gallic acid profile

gallate : A trihydroxybenzoate that is the conjugate base of gallic acid. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

ID Source	ID
PubMed CID	370
CHEMBL ID	288114
CHEBI ID	30778
SCHEMBL ID	15012
MeSH ID	M0008960

Synonym
BIDD:ER0374
CHEBI:30778 ,
nsc36997
nsc-36997
DIVK1C_006403
KBIO1_001347
SDCCGMLS-0066503.P001
nsc-674319
SPECTRUM_000342
benzoic acid,4,5-trihydroxy-
wln: qvr cq dq eq
nsc20103
nsc-20103
3,5-trihydroxybenzoic acid
gallic acid, tech.
acid, gallic
BSPBIO_001668
OPREA1_087792
SPECTRUM5_000108
nsc674319
ai3-16412
benzoic acid, 3,4,5-trihydroxy-
hsdb 2117
ccris 5523
NCGC00091125-01
einecs 205-749-9
kyselina 3,4,5-trihydroxybenzoova [czech]
nsc 674319
brn 2050274
nsc 20103
kyselina gallova [czech]
STK298718
149-91-7
pyrogallol-5-carboxylic acid
C01424
CPD-183 ,
gallic acid ,
gallate
3,4,5-trihydroxybenzoic acid
galop
inchi=1/c7h6o5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,8-10h,(h,11,12
gallic acid, 97.5-102.5% (titration)
NCGC00091125-03
NCGC00091125-02
KBIO2_003390
KBIO3_001168
KBIOGR_002008
KBIO2_005958
KBIO2_000822
KBIOSS_000822
SPECTRUM2_000399
SPBIO_000617
SPECTRUM3_000254
SPECPLUS_000307
SPECTRUM4_001544
SPECTRUM210369
NCGC00091125-04
78563C7D-0E2D-4766-A8EA-670A03C78FCF
HMS2091A07
AC-1206
3,4,5-trihydroxybenzoate, x
gallic acid, f
bdbm50085536
CHEMBL288114 ,
BMSE000389
gallic acid anhydrous
G0011
HMS1923K07
AKOS000119625
NCGC00091125-05
tox21_202515
NCGC00260064-01
GDE ,
BBL009937
nsc755825
nsc-755825
pharmakon1600-00210369
tox21_111089
cas-149-91-7
dtxsid0020650 ,
dtxcid60650
S4603
CCG-38670
kyselina 3,4,5-trihydroxybenzoova
gallic acid [nf]
3-10-00-02070 (beilstein handbook reference)
unii-632xd903sp
632xd903sp ,
kyselina gallova
FT-0626592
gallic acid [inci]
gallic acid [hsdb]
gallic acid [mi]
gallic acid [who-dd]
gtpl5549
BRD-K77345217-001-01-9
SCHEMBL15012
tox21_111089_1
NCGC00091125-07
Q-201146
PS-8710
3,4,5-trihydroxybenzoic acid;
AB00052697_03
mfcd00002510
F1908-0156
gallic acid, certified reference material, tracecert(r)
3,4,5-trihydroxybenzoic acid, anhydrous
SR-05000001537-3
sr-05000001537
gallic acid tech.
3,4,5-trihydroxy-benzoate
3,4,5-trihydroxy-benzoic acid
SR-05000001537-1
SR-05000001537-2
gallic acid, puriss., 98.0%
SBI-0052184.P002
CS-8191
BCP18127
5-trihydroxybenzoic acid
HY-N0523
137657-43-3
3,4,5-trihydroxybenzoic acid (acd/name 4.0)
Q375837
SY038078
gallic-acid
D85056
3,4,5-trihydroxybenzoicacid
EN300-21542
gallic acid1520
gallic acid (constituent of grape seeds oligomeric proanthocyanidins)
3,4,5-hydroxybenzoic acid
Z104501122

Excerpt	Reference	Relevance
"Gallic acid is a common botanic phenolic compound, which is present in plants and foods worldwide. "	( Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover. Nam, B; Rho, JK; Shin, DM; Son, J, 2016)	3.32
"Gallic acid (GA) is a phenolic acid with anti-amyloidogenic activity against Aβ in buffered solutions."	( Influence of in vitro neuronal membranes on the anti-amyloidogenic activity of gallic acid: Implication for the therapy of Alzheimer's disease. Andrade, S; Loureiro, JA; Pereira, MDC, 2021)	1.57
"Gallic acid (GA) is a phenolic acid exclusively found in natural sources such as gallnut, sumac, tea leaves, and oak bark."	( Gallic acid for cancer therapy: Molecular mechanisms and boosting efficacy by nanoscopical delivery. Ahn, KS; Ang, HL; Ashrafizadeh, M; Hashemi, F; Hushmandi, K; Khan, H; Kumar, AP; Makvandi, P; Mirzaei, S; Nabavi, N; Samarghandian, S; Sethi, G; Varma, RS; Zabolian, A; Zarrabi, A, 2021)	2.79
"Gallic acid (GA) is a polyphenolic agent with interesting pharmacological impacts on the cardiovascular system."	( Gallic acid protects against isoproterenol-induced cardiotoxicity in rats. Hesari, M; Hoseinkhani, Z; Ramezani-Aliakbari, F; Ramezani-Aliakbari, S; Shackebaei, D, )	3.02
"Gallic acid (GA) is a plant-derived triphenolic chemical with multiple cardio-protective properties, such as antiobesity, anti-inflammation, and antioxidation."	( Low-Dose Gallic Acid Administration Does Not Improve Diet-Induced Metabolic Disorders and Atherosclerosis in Apoe Knockout Mice. An, X; Bai, J; Liao, J; Lin, QY; Liu, S; Wang, Y; Xie, Y, 2022)	1.86
"Gallic acid (GA) is a secondary metabolite found in plants. "	( Gallic acid modulates purine metabolism and oxidative stress induced by ethanol exposure in zebrafish brain. Baldin, SL; Bernardo, HT; da Costa Pereira, B; de Farias, ACS; de Pieri Pickler, K; Dondossola, ER; Machado-de-Ávila, RA; Pacheco, SD; Rico, EP; Scussel, R; Wanderley, AG, 2022)	3.61
"Gallic acid is a phytophenol and shows high binding affinity toward the ACE-2 receptors, which may be helpful for better outcomes in the treatment of COVID-19 pathogenesis."	( Therapeutic Role of Phytophenol Gallic Acid for the Cure of COVID-19 Pathogenesis. Baraskar, K; Shrivastava, R; Shrivastava, VK; Thakur, P, 2023)	1.92
"Gallic acid (GA) is a natural ingredient in many traditional Chinese medicines, which has many biological activities, such as antibacterial, and antiseptic."	( Bactericidal activity of gallic acid against multi-drug resistance Escherichia coli. Bo, R; Li, J; Liu, M; Su, H; Tian, Q; Wei, S; Xu, S; Zheng, S, 2022)	1.75
"Gallic acid (GA) is a natural polyphenolic compound derived from Rhus chinensis Mill. "	( Gallic acid alleviates gastric precancerous lesions through inhibition of epithelial mesenchymal transition via Wnt/β-catenin signaling pathway. Chen, N; Li, Y; Liao, W; Lv, S; Mou, Y; Tang, J; Wan, L; Wang, J; Wen, Y; Zeng, J; Zhao, M; Zhao, Z; Zheng, Q, 2023)	3.8
"Gallic acid is a powerful antioxidant with multiple therapeutic applications, usually obtained from the acidic hydrolysis of tannins produced by many plants. "	( From degrader to producer: reversing the gallic acid metabolism of Pseudomonas putida KT2440. Dias, FMS; Gomez, JGC; Pantoja, RK; Silva, LF, 2023)	2.62
"Gallic acid (GA) is a naturally occurring phenolic acid with metabolic disease-related clinical significance and preclinical benefits."	( Gallic acid impairs fructose-driven de novo lipogenesis and ameliorates hepatic steatosis via AMPK-dependent suppression of SREBP-1/ACC/FASN cascade. Cao, P; Chen, L; Chen, X; Lu, Y; Qiu, Z; Song, Y; Yang, Y; Zhang, C; Zheng, G, 2023)	3.07
"Gallic acid is a phenolic acid present in various plants, nuts, and fruits. "	( Phenethyl Ester of Gallic Acid Ameliorates Experimental Autoimmune Encephalomyelitis. Antoniou, T; Dimitrijević, M; Djedovic, N; Gkalpinos, VK; Jevtić, B; Lazarević, M; Miljković, Đ; Momčilović, M; Stanisavljević, S; Stegnjaić, G; Tsiailanis, AD; Tzakos, AG, 2022)	2.49
"Gallic acid is a well-recognized naturally occurring compound possessing antioxidant activities. "	( Free radical scavenging activity of gallic acid toward various reactive oxygen, nitrogen, and sulfur species: a DFT approach. Das, DK; Mittal, A; Vashistha, VK, 2023)	2.63
"Gallic acid (GA) is an endogenous plant polyphenol found in fruits, nuts, and plants that has antioxidant, antimicrobial, and growth-promoting effects. "	( An evaluation of gallic acid supplementation to corn-soybean-gluten meal-based diet in broilers. Biswas, S; Cho, SB; Kim, IH, 2023)	2.69
"Gallic acid (GA) is a triphenolic compound with beneficial biological activities including anti-inflammatory, antidiabetic, antihypertensive, and antioxidant effects."	( Gallic acid as a Sestrin (SESN2) activator and potential obesity therapeutic agent: A molecular docking study. Aguilar, CM; de Paula, AMB; Guimarães, ALS; Lescano, CH; Pires de Oliveira, I; Queiroz, LDRP; Santos, SHS; Sousa, JN, 2023)	3.07
"Gallic acid (GA) is a phenolic compound derived from a wide range of fruits."	( Mitochondrial biogenesis and apoptosis as underlying mechanisms involved in the cardioprotective effects of Gallic acid against D-galactose-induced aging. Karimi, SA; Ramezani-Aliakbari, F; Raoufi, S; Sarihi, A; Zamani, A; Zarei, M, 2023)	1.84
"Gallic acid is a type of phenolic acid that has been shown to be a potential drug candidate to treat diabetic kidney disease, an important complication of diabetes."	( Gallic acid improves the metformin effects on diabetic kidney disease in mice. Hong, Y; Sun, W; Wang, J; Xu, X; Zhang, K; Zhang, L, 2023)	3.07
"Gallic acid (GA) is a natural anti-cancer compound that can be found in many food sources, including edible mushrooms, fruits, and vegetables. "	( Gallic Acid Triggers Iron-Dependent Cell Death with Apoptotic, Ferroptotic, and Necroptotic Features. Cheung, PCK; Tang, HM, 2019)	3.4
"Gallic acid (GA) is a natural polyphenol with remarkable antioxidant power present in several vegetables and fruits. "	( Biodegradable and biocompatible spherical dendrimer nanoparticles with a gallic acid shell and a double-acting strong antioxidant activity as potential device to fight diseases from "oxidative stress". Alfei, S; Catena, S; Turrini, F, 2020)	2.23
"Gallic acid (GA) is a plant polyphenol that has been used against CIRI."	( Improved Neuroprotective Effects of Gallic Acid-Loaded Chitosan Nanoparticles Against Ischemic Stroke. Li, D; Sun, Y; Zhao, Y; Zhu, Z, 2020)	1.55
"Gallic acid (GA) is a natural free radical "scavenger." We evaluated the GA protective role regarding binge or subchronic (SbChro) KET-induced toxicity in adolescent rats."	( Binge and Subchronic Exposure to Ketamine Promote Memory Impairments and Damages in the Hippocampus and Peripheral Tissues in Rats: Gallic Acid Protective Effects. Brum, GF; Burger, ME; Metz, VG; Milanesi, LH; Rosa, HZ; Rosa, JLO; Rossato, DR, 2020)	1.48
"Gallic acid is a phenolic compound that has antioxidant properties."	( Gallic acid exerts anti-inflammatory, anti-oxidative stress, and nephroprotective effects against paraquat-induced renal injury in male rats. Heibati, F; Heidarian, E; Nouri, A, 2021)	2.79
"Gallic acid (GA) is a natural polyphenol, which exhibits a broad spectrum of biological activities, but its therapeutic application was limited due to poor bioavailability and toxicity."	( Surface modified PAMAM dendrimers with gallic acid inhibit, cell proliferation, cell migration and inflammatory response to augment apoptotic cell death in human colon carcinoma cells. Kumar, A; Pathak, C; Priyadarshi, K; Sharma, A; Shirsath, K; Waghela, NB, 2021)	1.61
"Gallic acid (GA) is a polyphenolic compound with proven efficacy against hepatic fibrosis in experimental animals. "	( Impact of Reverse Micelle Loaded Lipid Nanocapsules on the Delivery of Gallic Acid into Activated Hepatic Stellate Cells: A Promising Therapeutic Approach for Hepatic Fibrosis. El-Maadawy, WH; ElMeshad, AN; Radwan, SAA; Shoukri, RA; Yousry, C, 2020)	2.23
"Gallic acid (GA) is a widespread naturally occurring phenolic acid and one of the main active monomers that forms polyphenols such as tannins. "	( Gallic acid as a key substance to inhibit proliferation and adipogenesis in bovine subcutaneous adipocyte. Jin, Q; Liu, G; Liu, X; Tan, X; Wei, C; Zhang, X, 2022)	3.61
"Gallic acid (GA) is a representative phenolic substance and was used to test the adsorption properties of the prepared AMCS."	( Arginine-modified magnetic chitosan: Preparation, characterization and adsorption of gallic acid in sugar solution. Chai, Z; Chen, D; Chen, M; Li, C; Liang, X; Song, X; Wu, J; Yang, Y; Zhu, Y, 2020)	1.5
"Gallic acid (GA) is a naturally occurring polyphenol compound present in fruits, vegetables, and herbal medicines. "	( Impact of Gallic Acid on Gut Health: Focus on the Gut Microbiome, Immune Response, and Mechanisms of Action. Deng, B; Deng, J; Liao, P; Sindaye, D; Tan, C; Xiao, Z; Xin, Z; Yang, K; Yin, Y; Zhang, F; Zhang, L, 2020)	2.4
"Gallic acid (GA) is a natural phenolic compound with therapeutic effects that are often challenged by its rapid metabolism and clearance. "	( Preparation, characterization and therapeutic properties of gum arabic-stabilized gallic acid nanoparticles. Azarian, MMS; Hassani, A; Hussain, SA; Ibrahim, WN, 2020)	2.23
"Gallic acid (GA) is an important active ingredient for its pharmacological activities. "	( Metabolite and Microbiome Profilings of Pickled Tea Elucidate the Role of Anaerobic Fermentation in Promoting High Levels of Gallic Acid Accumulation. Chen, WJ; Huang, YY; Liu, YZ; Wu, S; Xu, WC; Zhang, H, 2020)	2.21
"Gallic acid (GA) is a polyphenolic compound that has attracted significant interest due to its antioxidant action through free radical elimination and metal chelation. "	( Gallic Acid Reverses Neurochemical Changes Induced by Prolonged Ethanol Exposure in the Zebrafish Brain. Agostini, JF; Baldin, SL; Bernardo, HT; de Farias, ACS; Rico, EP; Santo, GD; Wanderley, AG, 2021)	3.51
"Gallic acid is an active phenolic acid widely distributed in plants, and there is compelling evidence to prove its anti-inflammatory effects. "	( Gallic Acid Alleviates Gouty Arthritis by Inhibiting NLRP3 Inflammasome Activation and Pyroptosis Through Enhancing Nrf2 Signaling. Chen, D; Fu, Z; Huang, X; Li, X; Li, Y; Lin, Y; Liu, A; Luo, T; Pan, H; Weng, A; Yao, Y, 2020)	3.44
"Gallic acid is a well-established antioxidant, presenting a promising new selective anti-cancer drug, while gold nanoparticles (GNPs) can be developed as versatile nontoxic carriers for anti-cancer drug delivery."	( Gallic acid-gold nanoparticles enhance radiation-induced cell death of human glioma U251 cells. Fu, X; Hu, W; Jing, Z; Li, M; Liang, W; Ma, J; Meng, E; Wang, H; Wang, X; Yang, Z; Zhang, H; Zhou, S, 2021)	2.79
"Gallic acid is a phenolic compound which affects several pharmacological and biochemical pathways and has strong antioxidant, anti-inflammatory, antimutagenic and anticancer properties."	( Identification of novel anti-cancer agents, applying Minuchehr, Z; Sabouni, F; Taghvaei, A; Taghvaei, S, 2022)	1.44
"Gallic acid is a phenolic compound with biological and pharmacological activities. "	( Hepatoprotective effect of gallic acid against type 2-induced diabetic liver injury in male rats through modulation of fetuin-A and GLP-1 with involvement of ERK1/2/NF-κB and Wnt1/β-catenin signaling pathways. Abd-Elmoniem, HA; Bashar, SM; Elhadidy, MG; Hamed, B; Helmy, S; Mostafa, AF, 2021)	2.36
"Gallic acid (GA) is an abundant natural polyphenolic compound found in vegetable and fruits that reduces the cardiac disease risk factor. "	( Gallic acid attenuates cadmium mediated cardiac hypertrophic remodelling through upregulation of Nrf2 and PECAM-1signalling in rats. Andiapppan, R; Christopher, G; John, S; Paneerselvam, G; Selvam, GS; Sundaresan, S, 2021)	3.51
"Gallic acid is a phenolic compound that exhibits antibacterial, antioxidative and anti-inflammatory functions. "	( Gallic acid mitigates LPS-induced inflammatory response via suppressing NF-κB signalling pathway in IPEC-J2 cells. Cai, L; Jiang, X; Li, X; Li, Y; Wei, Z; Zhao, X, 2022)	3.61
"Gallic acid is a natural phenolic compound that displays anti-cancer properties in clinically relevant cell culture and rodent models. "	( Gene expression profile analysis of gallic acid-induced cell death process. Cheung, PCK; Tang, HM, 2021)	2.34
"Gallic acid (GA) is a polyphenol natural compound found in many medicinal plant species, including pomegranate rind (Punica granatum L.), and has been shown to have antiinflammatory and antibacterial properties. "	( Antifungal Activity of Gallic Acid In Vitro and In Vivo. Aibai, S; Dawuti, G; Dou, Q; Li, ZJ; Liu, HG; Liu, M; Ma, Y, 2017)	2.21
"Gallic acid (GA) is a naturally occurring compound with valuable antioxidant activity. "	( Gallic acid-PAMAM and gallic acid-phospholipid conjugates, physicochemical characterization and in vivo evaluation. Abdou, EM; Masoud, MM, 2018)	3.37
"Gallic acid (GA) is a naturally occurring phytochemical that has strong antioxidant and antibacterial activities. "	( Rational engineering of p-hydroxybenzoate hydroxylase to enable efficient gallic acid synthesis via a novel artificial biosynthetic pathway. Chen, Z; Shen, X; Wang, J; Yan, Y; Yuan, Q, 2017)	2.13
"Gallic acid is a trihydroxybenzoic acid found in natural herbal plants. "	( Gallic Acid Inhibited Matrix Invasion and AP-1/ETS-1-Mediated MMP-1 Transcription in Human Nasopharyngeal Carcinoma Cells. Huang, ST; Pang, JS; Wu, HT; Yen, JH, 2017)	3.34
"Gallic acid (GA) is a phenolic acid that is widespread in plant foods."	( Influence of gallic acid on α-amylase and α-glucosidase inhibitory properties of acarbose. Adefegha, SA; Oboh, G; Ogunbadejo, MD; Ogunsuyi, OB, 2016)	1.52
"Gallic acid is a polyphenolic compost appointed to interfere with neoplastic cells behavior. "	( Gallic acid modulates phenotypic behavior and gene expression in oral squamous cell carcinoma cells by interfering with leptin pathway. Batista, PR; da Rocha, RG; da Silveira, LH; de Carvalho Fraga, CA; de Oliveira, PSL; de Paula, AMB; Farias, LC; Guimarães, ALS; Guimarães, TA; Melo, GA; Santos, EMS; Santos, HO; Santos, SH, 2018)	3.37
"Gallic acid is a phytochemical having wide range of biological activities."	( Gallic acid attenuates type I diabetic nephropathy in rats. Garud, MS; Kulkarni, YA, 2018)	2.64
"Gallic acid is a trihydroxybenzoic acid found to exert an anticancer effect against a variety of cancer cells."	( Gallic Acid Induces Apoptosis in Human Gastric Adenocarcinoma Cells. Chiu, YM; Ho, TY; Hsieh, CT; Lee, YJ; Shieh, DC; Tsai, CL; Tsay, GJ; Wu, YY, 2018)	2.64
"Gallic acid is a trihydroxybenzoic acid found in tea leaves and some plants. "	( Gallic acid improves cardiac dysfunction and fibrosis in pressure overload-induced heart failure. Choi, SY; Jeong, MH; Jin, L; Kee, HJ; Kim, GR; Kim, HS; Liu, B; Piao, ZH; Ryu, Y; Sun, S, 2018)	3.37
"Gallic acid is a powerful anti-inflammatory agent."	( Gallic acid attenuates allergic airway inflammation via suppressed interleukin-33 and group 2 innate lymphoid cells in ovalbumin-induced asthma in mice. Feng, J; Han, S; Lv, L; Ma, C; Wang, X; Zhao, H, 2018)	2.64
"Gallic acid derivative is a derivative of Gallic acid that can be extracted from Chinese herbal medicine."	( A novel Gallic acid derivative attenuates BLM-induced pulmonary fibrosis in mice. Cao, B; Chen, H; Chen, Y; Li, W; Liu, B; Liu, T; Liu, Y; Rong, Y, 2018)	1.64
"Gallic acid (GA) is an important phenolic compound possessing various pharmacological properties including anti-inflammatory, antioxidant and free radical scavenging activities."	( Ameliorative effect of gallic acid on sodium arsenite-induced spleno-, cardio- and hemato-toxicity in rats. Goudarzi, M; Hosseinzadeh, A; Houshmand, G; Kalantar, M; Mansouri, E; Mehrzadi, S; Sezavar, SH, 2019)	1.55
"Gallic acid (GA) is a dietary phenolic acid found in tea, red wine, and some plants. "	( Gallic Acid Suppresses Cardiac Hypertrophic Remodeling and Heart Failure. Chen, C; Li, HH; Liu, Y; Xia, YL; Yan, X; Zhang, L; Zhang, YL; Zou, LX, 2019)	3.4
"Gallic acid (GA) is an important phenolic compound, which could protect different tissues from oxidative stress induced damage."	( Gallic acid ameliorates sodium arsenite-induced renal and hepatic toxicity in rats. Gholamine, B; Goudarzi, M; Hosseinzadeh, A; Houshmand, G; Kalantar, M; Mehrzadi, S, 2021)	2.79
"Gallic acid (GA) is a well-known antioxidant compound, found in tea leaves, various fruits, fruit seeds and in fruit-derived foods and beverages."	( Electrochemical strategies for gallic acid detection: Potential for application in clinical, food or environmental analyses. Aleya, L; Badea, GE; Badea, M; Bungau, S; di Modugno, F; Floroian, L; Iovan, C; Restani, P; Tit, DM, 2019)	1.52
"Gallic acid (GA) is an anticancer agent and effective against many types of tumor cells."	( Synthesis of dual functional gallic-acid-based carbon dots for bioimaging and antitumor therapy. Li, J; Li, Z; Liu, L; Lu, S; Qu, Z; Sui, G; Sun, T; Wang, H; Wang, T; Zhao, W, 2019)	1.24
"Gallic acid (GA) is an interesting pharmaceutical component of plants. "	( Preparation, characterization and in vitro release study of gallic acid loaded silica nanoparticles for controlled release. Feng, S; Hu, H; Nie, L; Suo, J, 2013)	2.07
"Gallic acid is a polyphenolic compound and is reported to be renoprotective because of its antioxidant activity in various preclinical studies. "	( Explicit role of peroxisome proliferator-activated receptor gamma in gallic acid-mediated protection against ischemia-reperfusion-induced acute kidney injury in rats. Bhatti, R; Singh, AP; Singh, JP, 2014)	2.08
"Gallic acid (GA) is a polyphenolic compound commonly found in green tea and various berries and possesses a wide range of biological activities."	( Gallic acid functions as a TRPA1 antagonist with relevant antinociceptive and antiedematogenic effects in mice. Athayde, ML; Boligon, AA; Ferreira, J; Hoffmeister, C; Klafke, JZ; Pinheiro, FV; Pinheiro, KV; Rosa, F; Rossato, MF; Tonello, R; Trevisan, G, 2014)	2.57
"Gallic acid (GA) is a natural product that induces cell death through cell cycle arrest and induction of apoptosis."	( Gallic acid inhibits migration and invasion of SCC-4 human oral cancer cells through actions of NF-κB, Ras and matrix metalloproteinase-2 and -9. Chung, JG; Kuo, CL; Lai, KC; Lin, JP; Ma, YS; Weng, SW, 2014)	2.57
"Gallic acid is a well known antioxidant compounds which has neuroprotective actions in different models of neurodegeneration, neurotoxicity and oxidative stress."	( Polyphenols: well beyond the antioxidant capacity: gallic acid and related compounds as neuroprotective agents: you are what you eat! Daglia, M; Di Lorenzo, A; Nabavi, SF; Nabavi, SM; Talas, ZS, 2014)	1.38
"Gallic acid is a phytochemical derived from various herbs, and has anti-fungal, anti-viral, and antioxidant properties."	( Galloyl-RGD as a new cosmetic ingredient. Jung, DH; Kim, SH; Kim, SJ; Park, DH; Park, KM, 2014)	1.12
"Gallic acid is a ubiquitous compound, widely distributed in the vegetal kingdom and frequently found in the human diet. "	( Radical scavenging ability of gallic acid toward OH and OOH radicals. Reaction mechanism and rate constants from the density functional theory. Galano, A; Marino, T; Russo, N, 2014)	2.13
"1.Gallic acid is a main polyphenol in various fruits and plants. "	( Time-dependent inhibition of CYP3A4 by gallic acid in human liver microsomes and recombinant systems. Pu, QH; Shi, L; Yu, C, 2015)	1.41
"Gallic acid is unlikely to be an effective antimicrobial against Campylobacter in a practical sense unless further interventions to ensure an effective bactericidal mode of action against all strains are developed."	( Antimicrobial activity of gallic acid against thermophilic Campylobacter is strain specific and associated with a loss of calcium ions. Dykes, GA; Sarjit, A; Wang, Y, 2015)	1.44
"Gallic acid is a polyhydroxy phenolic compound found in various natural products."	( Gallic Acid Decreases Inflammatory Cytokine Secretion Through Histone Acetyltransferase/Histone Deacetylase Regulation in High Glucose-Induced Human Monocytes. Lee, SY; Lee, W; Son, YJ; Yun, JM, 2015)	2.58
"As gallic acid (GA) is a hydrolysated natural product of tannin in Chinese gall, this research studied the effects of GA on the growth and biofilm formation of bacteria (Escherichia coli [Gram-negative] and Streptococcus mutans [Gram-positive]) under different conditions, such as nutrient levels, temperatures (25 and 37 °C) and incubation times (24 and 48 h)."	( Inhibition of Gallic Acid on the Growth and Biofilm Formation of Escherichia coli and Streptococcus mutans. Huang, Q; Li, J; Liu, L; Shao, D; Shi, J; Tang, R; Yang, H, 2015)	1.29
"Gallic acid (GA) is a naturally occurring plant polyphenol compound. "	( Characteristics and kinetics of hexavalent chromium reduction by gallic acid in aqueous solutions. Chen, Z; Li, Q; Zhao, Y, 2015)	2.1
"Gallic acid (GA) is a polyhydroxy phenolic compound that has been detected in various natural products, such as green tea, strawberries, grapes, bananas, and many other fruits. "	( Gallic acid attenuates dextran sulfate sodium-induced experimental colitis in BALB/c mice. Looi, CY; Mohebali, N; Norhaizan, ME; Pandurangan, AK, 2015)	3.3
"Gallic acid (GA) is a model hydroxybenzoic acid that occurs esterified in the lignocellulosic biomass of higher plants. "	( Molecular adaptation of Lactobacillus plantarum WCFS1 to gallic acid revealed by genome-scale transcriptomic signature and physiological analysis. de las Rivas, B; López de Felipe, F; Matesanz, R; Muñoz, R; Reverón, I, 2015)	2.1
"Gallic acid is an important polyphenol compound presenting various biological activities. "	( Nanoencapsulation of gallic acid and evaluation of its cytotoxicity and antioxidant activity. de Cristo Soares Alves, A; Khalil, NM; Mainardes, RM, 2016)	2.2
"Gallic acid (GA) is a polyphenol present in many plants. "	( Antioxidant Capacity of Gallic Acid in vitro Assayed on Human Erythrocytes. Colina, J; Gallardo, MJ; Jemiola-Rzeminska, M; Manrique-Moreno, M; Sepúlveda, B; Strzalka, K; Suwalsky, M, 2016)	2.18
"Gallic acid (GA) is a polyhydroxy phenolic compound which can inhibit the growth of cancer cells."	( The reduction of IL-6 gene expression, pAKT, pERK1/2, pSTAT3 signaling pathways and invasion activity by gallic acid in prostate cancer PC3 cells. Ghatreh-Samani, K; Heidarian, E; Keloushadi, M; Valipour, P, 2016)	1.37
"Gallic acid is a phenolic acid found in many natural products and have shown anti-inflammatory, anti-tumor, anti-mutagenic and antioxidant actions."	( Gallic acid reduces cell growth by induction of apoptosis and reduction of IL-8 in HepG2 cells. Basso, BS; Catarina, AV; Chiela, ECF; De Mesquita, FC; De Oliveira, JR; Dias, HB; Donadio, MVF; Haute, GV; Jaeger, N; Krause, GC; Lima, KG; Marczak, ES; Martha, BA; Nunes, FB; Pedrazza, L; Schuster, AD; Thomé, MP, 2016)	2.6
"Gallic acid is a naturally available polyphenol, possess strong antioxidant activity with a capacity to inhibit the formation of tumors in several cancer models."	( Antiproliferative potential of gallic acid against diethylnitrosamine-induced rat hepatocellular carcinoma. Anandakumar, P; Devaki, T; Jagan, S; Kamaraj, S; Ramakrishnan, G, 2008)	1.35
"Gallic acid (GA) is a polyphenol widely present in tea and other plants which is popularly used in the traditional medicine of China."	( Chemopreventive efficacy of gallic acid, an antioxidant and anticarcinogenic polyphenol, against 1,2-dimethyl hydrazine induced rat colon carcinogenesis. Giftson, JS; Jayanthi, S; Nalini, N, 2010)	1.38
"Gallic acid is a polyhydroxyphenolic compound which can be found in various natural products. "	( Gallic acid inhibits murine leukemia WEHI-3 cells in vivo and promotes macrophage phagocytosis. Chiang, JH; Chiu, TH; Chung, JG; Ho, CC; Lin, SY; Liu, KC; Lu, CC; Tang, YJ; Wu, CL; Yang, JS; Yang, MD, )	3.02
"Gallic acid is a normal constituent of many edible foods, thus directly interacts with epithelial tissue in intestine. "	( Effect of gallic acid on alkaline phosphatase and peptidase activities in rat intestine. Mahajan, N; Mahmood, A, 2009)	2.2
"Gallic acid (GA) is a natural polyphenol, and we tested its in-vitro cytotoxicity after 24 h in prostate cancer LNCaP cells."	( Autoxidation of gallic acid induces ROS-dependent death in human prostate cancer LNCaP cells. Agharahimi, M; Badisa, RB; Goodman, CB; Mazzio, E; Oriaku, ET; Russell, LH; Zhu, ZP, 2012)	1.45
"Gallic acid (GA) is a plant phenol isolated from water caltrop which is reported to have anti-inflammatory and anti-cancer effects. "	( Gallic acid as a cancer-selective agent induces apoptosis in pancreatic cancer cells. Li, D; Liu, Z; Niu, F; Yu, L, 2012)	3.26
"Gallic acid is a natural polyphenolic acid found in gall nuts, sumac, oak bark, tea leaves, grapes and wine, with potent antioxidant and antiapoptotic activity."	( Gallic acid decreases vacuous chewing movements induced by reserpine in rats. Bürger, ME; de Freitas, CM; Fachinetto, R; Ferrari, MC; Peroza, LR; Reckziegel, P; Schaffer, LF, 2013)	2.55
"Gallic acid (GA) is a phenolic compound, which has been reported to suppress melanogenesis in melanoma cells. "	( In vitro and in vivo studies disclosed the depigmenting effects of gallic acid: a novel skin lightening agent for hyperpigmentary skin diseases. Hseu, YC; Hsu, LS; Kumar, KJ; Liao, JW; Vani, MG; Wang, SY; Yang, HL, )	1.81
"Gallic acid (GA) is a naturally occurring polyhydroxyphenolic compound and an excellent free radical scavenger. "	( Gallic acid inhibits ribonucleotide reductase and cyclooxygenases in human HL-60 promyelocytic leukemia cells. Bernhaus, A; Elford, HL; Fritzer-Szekeres, M; Grusch, M; Herbacek, I; Horvath, Z; Illmer, C; Krupitza, G; Losert, A; Madlener, S; Saiko, P; Szekeres, T, 2007)	3.23
"Gallic acid was found to be a major compound in the ethyl acetate extract and Geraniin showed highest NO scavenging activity among the isolated compounds."	( Nitric oxide radical scavenging active components from Phyllanthus emblica L. Karunakaran, RJ; Kumaran, A, 2006)	1.06
"Gallic acid (GA) is a naturally abundant plant phenolic compound in the human diet and is known to reduce the risk of disease. "	( Effect of gallic acid on high fat diet-induced dyslipidaemia, hepatosteatosis and oxidative stress in rats. Hsu, CL; Yen, GC, 2007)	2.18
"Gallic acid (GA) is a common part of the human diet, both in the free form and as a metabolite of tannic acid and propyl gallate. "	( Reduction in antiviral activity of human beta interferon by gallic acid. Archer, DL; Osborne, LC; Peeler, JT, 1981)	1.95
"Gallic acid is a naturally occurring plant phenol obtained by the hydrolysis of tannins and is known to show some pharmacological activities. "	( Assessment of the no-observed-adverse-effect level (NOAEL) of gallic acid in mice. Devaraj, H; Niranjali Devaraj, S; Rajalakshmi, K, 2001)	1.99
"Gallic acid is a polyphenol present in carcinogenic oak wood dust, but not in beech, ash, pine or spruce dusts, as confirmed by HPLC analyses."	( Determination of gallic acid in wood dust as an indicator of oak content. Kangas, J; Lindroos, L; Mämmelä, P; Savolainen, H; Tuomainen, A; Vartiainen, T, 2001)	1.37

Excerpt	Reference	Relevance
"Gallic acid and hispidin have been previously described by us as inhibitors of horseradish peroxidase (Benarous, K., Benali, F. "	( In vitro oxidation of hispidin and gallic acid by horseradish peroxidase. Benarous, K; Tarasek, D; Wojtasek, H; Yousfi, M, 2023)	2.63
"Gallic acid has been reported to mitigate cardiac hypertrophy, fibrosis and arterial hypertension. "	( Syringic acid mitigates isoproterenol-induced cardiac hypertrophy and fibrosis by downregulating Ereg. Bai, L; Han, X; Jeong, MH; Kee, HJ, 2022)	2.16
"Gallic acid (GA) has attracted extensive attention due to its excellent health benefits. "	( Construction of double network hydrogels using agarose and gallic acid with antibacterial and anti-inflammatory properties for wound healing. Gong, W; Gong, X; He, W; Hou, Y; Hu, J; Huang, H; Wang, R; Wang, X, 2023)	2.6
"Gallic Acid (GA) has shown efficacious results against the hyperproliferation of keratinocytes while lipid-polymer loaded hybrid nanoparticles (LPHNs) have an edge over lipidic and polymeric nanoparticles considering drug loading, controlled release, stability, and retention."	( Self-assembled Gallic acid loaded lecithin-chitosan hybrid nanostructured gel as a potential tool against imiquimod-induced psoriasis. Abourehab, MAS; Hazari, SA; Kesharwani, P; Sheikh, A; Tulbah, AS, 2023)	1.98
"Gallic acid has received a significant amount of interest for its biological properties. "	( Co-production of gallic acid and a novel cell-associated tannase by a pigment-producing yeast, Sporidiobolus ruineniae A45.2. Haltrich, D; Kanpiengjai, A; Khanongnuch, C; Kittibunchakul, S; Lumyong, S; Nguyen, TH, 2020)	2.34
"Gallic acid has been shown to both modulate factors leading to the onset of neurodegenerative disorders, as well as directly inhibit amyloid formation."	( Gallic acid oxidation products alter the formation pathway of insulin amyloid fibrils. Sakalauskas, A; Smirnovas, V; Ziaunys, M, 2020)	2.72
"Gallic acid has enhanced the stability of hazelnut oil against oxidation ~3 times over that of pure sample."	( Enrichment of Hazelnut Oil with Several Polyphenols: An Alternative Approach to A New Functional Food. Bilgin, M; Güçlü, K; Gülmez, Ö; Özyürek, M; Şahin, S, 2021)	1.34
"Gallic acid has been reported to possess a number of psychopharmacological activities. "	( Protective effect of gallic acid in experimental model of ketamine-induced psychosis: possible behaviour, biochemical, neurochemical and cellular alterations. Dhingra, MS; Dhingra, S; Jindal, DK; Kumar, A; Parle, M; Yadav, M, 2018)	2.24
"Gallic acid has inhibitory effects on fluoxetine-induced liver damage. "	( Anti-inflammatory and ameliorative effects of gallic acid on fluoxetine-induced oxidative stress and liver damage in rats. Amini, SA; Heidarian, E; Karimi-Khouzani, O, 2017)	2.16
"Gallic acid has been reported to inhibit the migration and invasive capability of various cancers."	( Gallic Acid Inhibited Matrix Invasion and AP-1/ETS-1-Mediated MMP-1 Transcription in Human Nasopharyngeal Carcinoma Cells. Huang, ST; Pang, JS; Wu, HT; Yen, JH, 2017)	2.62
"Gallic acid (GA) has been reported to have beneficial effects on cancer, vascular calcification, and diabetes-induced myocardial dysfunction. "	( Gallic Acid Reduces Blood Pressure and Attenuates Oxidative Stress and Cardiac Hypertrophy in Spontaneously Hypertensive Rats. Choi, SY; Jeong, MH; Jin, L; Kee, HJ; Kim, GR; Lin, MQ; Liu, B; Piao, ZH; Ryu, Y; Seok, YM; Sun, S, 2017)	3.34
"Gallic acid (GA) has been shown to inhibit carcinogenesis in animal models and various cancer cell lines."	( Gallic acid inhibits bladder cancer cell proliferation and migration via regulating fatty acid synthase (FAS). Chen, SC; Huang, HP; Liao, CC; Wang, CJ, 2018)	2.64
"Gallic acid has received a great deal of attention as a molecule of enormous therapeutic and indusrial potential."	( Recent trends and advancements in microbial tannase-catalyzed biotransformation of tannins: a review. Dhiman, S; Mukherjee, G; Singh, AK, 2018)	1.2
"Gallic acid (GA) has well-documented antioxidant and CNS effects affecting glutathione, catalase and malonaldehyde levels in brain."	( Nanoparticle mediated brain targeted delivery of gallic acid: in vivo behavioral and biochemical studies for protection against scopolamine-induced amnesia. Mishra, DN; Nagpal, K; Singh, SK, )	1.83
"Gallic acid has been identified as an antioxidant component of the edible and medicinal plant Peltiphyllum peltatum. "	( In vivo protective effects of gallic acid isolated from Peltiphyllum peltatum against sodium fluoride-induced oxidative stress in rat erythrocytes. Daglia, M; Habtemariam, S; Hajizadeh Moghaddam, A; Nabavi, SF; Nabavi, SM; Sureda, A, 2013)	2.12
"Gallic acid has been shown to possess cytotoxic properties in several cancer cell lines and to inhibit carcinogenesis in animal models."	( Dietary gallic acid and anthocyanin cytotoxicity on human fibrosarcoma HT1080 cells. A study on the mode of action. Carbajo, RJ; de Pascual-Teresa, B; de Pascual-Teresa, S; Fabre, B; Filipiak, K; Hidalgo, M; Pineda-Lucena, A; Ramos, A; Silvan, JM, 2014)	1.56
"Gallic acid has been reported to activate peroxisome proliferator-activated receptor gamma (PPAR-γ) in vitro."	( Explicit role of peroxisome proliferator-activated receptor gamma in gallic acid-mediated protection against ischemia-reperfusion-induced acute kidney injury in rats. Bhatti, R; Singh, AP; Singh, JP, 2014)	1.36
"Gallic acid (GA) has long been associated with a wide range of biological activities. "	( Proteomic study reveals a co-occurrence of gallic acid-induced apoptosis and glycolysis in B16F10 melanoma cells. Hsu, JL; Lin, JJ; Liu, C; Tsai, CC; Wu, YJ; Yang, ZY, 2014)	2.11
"Gallic acid has been suggested as a potential antimicrobial for the control of Campylobacter but its effectiveness is poorly studied. "	( Antimicrobial activity of gallic acid against thermophilic Campylobacter is strain specific and associated with a loss of calcium ions. Dykes, GA; Sarjit, A; Wang, Y, 2015)	2.16
"Gallic acid (GA) has been shown to inhibit demineralization and enhance remineralization of enamel; however, GA solution is highly acidic. "	( Changes in composition and enamel demineralization inhibition activities of gallic acid at different pH values. Deng, M; Huang, S; Huang, X; Li, J; Liu, H; Liu, M; Ten Cate, JM; Xie, X; Zhang, J; Zhou, X, 2015)	2.09
"Gallic acid has been covalently conjugated to SBA-15 mesoporous silica surface through different linkers. "	( SBA-15 Mesoporous Silica Modified with Gallic Acid and Evaluation of Its Cytotoxic Activity. Kurczewska, J; Lewandowski, D; Pińska, A; Ruszkowski, P; Schroeder, G, 2015)	2.13
"Gallic acid has potent antioxidant properties."	( Effects of gallic acid on delta - aminolevulinic dehydratase activity and in the biochemical, histological and oxidative stress parameters in the liver and kidney of diabetic rats. Baldissareli, J; Chitolina Schetinger, MR; da Costa Krewer, C; da Silva Pereira, A; de Oliveira, JS; de Oliveira, LS; Lopes, TF; Morsch, VM; Reichert, KP; Spanevello, RM; Thomé, GR, 2016)	1.55
"Gallic acid (GA) has various biological properties including anti-cancer effect. "	( Enhancement of gallic acid-induced human pulmonary fibroblast cell death by N-acetyl cysteine and L-buthionine sulfoximine. Park, WH; You, BR, 2011)	2.16
"Gallic acid (GA) has various biological properties, including an anti-cancer effect. "	( MAPK inhibitors differentially affect gallic acid-induced human pulmonary fibroblast cell growth inhibition. Park, WH, )	1.85
"Gallic acid (GA) has been demonstrated to possess multiple biological activities including anticancer function."	( Gallic acid suppresses the migration and invasion of PC-3 human prostate cancer cells via inhibition of matrix metalloproteinase-2 and -9 signaling pathways. Chiang, JH; Chueh, FS; Chung, JG; Huang, AC; Lin, HY; Liu, KC; Lu, CC; Meng, M; Wu, PP; Yang, JS, 2011)	2.53
"Gallic acid (GA) has various biological effects including apoptosis. "	( Involvement of reactive oxygen species and glutathione in gallic acid-induced human umbilical vein endothelial cell death. Kim, SH; Park, WH, 2012)	2.07
"Gallic acid therapy has significantly reduced the increase in these biomarkers, indicating a possible hepatoprotective effect of gallic acid."	( Investigation of the possible protective role of gallic acid on paraoxanase and arylesterase activities in livers of rats with acute alcohol intoxication. Bayramoğlu, G; Canbek, M; Kanbak, G; Kartkaya, K; Oğlakçi, A; Şentürk, H, 2013)	1.37
"Gallic acid has been reported to be responsible for the invasive success of nonnative genotypes of Phragmites australis in North America. "	( Evidence does not support a role for gallic acid in Phragmites australis invasion success. Allman, J; Bergosh, RG; Li, M; Posner, M; Weidenhamer, JD, 2013)	2.11
"Gallic acid has been modified to naphthophenone derivatives with esterified fatty acid side chain. "	( Synthesis of a novel plant growth promoter from gallic acid. Bhattacharya, AK; Chattopadhyay, SK; Darokar, MP; Garg, A; Khanuja, SP; Negi, AS; Srivastava, V, 2005)	2.03

Excerpt	Reference	Relevance
"Gallic acid could also lower the concentration of hydrocortisone required to inhibit the activation of DC."	( Gallic Acid Is the Major Active Component of Cortex Moutan in Inhibiting Immune Maturation of Human Monocyte-Derived Dendritic Cells. Chan, BC; Hon, KL; Hu, SQ; Hui, PC; Lau, CB; Leung, PC; Li, LF; Wat, E; Wong, CK; Wong, EC; Zhang, VX, 2015)	2.58
"Gallic acid was chosen because it shows anticancer activity without harming health cells."	( Complexation and molecular modeling studies of europium(III)-gallic acid-amino acid complexes. Coutinho, JA; Khan, I; Taha, M, 2016)	1.4
"Gallic acid (GA) can inhibit the growth of human cancer cells in vitro and in vivo."	( Gallic acid inhibits the migration and invasion of A375.S2 human melanoma cells through the inhibition of matrix metalloproteinase-2 and Ras. Chen, HY; Chung, JG; Lai, TY; Lin, HY; Lin, JG; Lo, C; Ma, YS; Weng, SW; Yang, JH; Yang, JS, 2011)	2.53
"Gallic acid at lower doses significantly, but not completely, scavenged the eugenol radical."	( Effect of antioxidants on radical intensity and cytotoxic activity of eugenol. Fujisawa, S; Ida, Y; Sakagami, H; Satoh, K; Tanaka, T, )	0.85

Excerpt	Reference	Relevance
"Gallic acid and lutein treatment caused a significant reduction of KKU055, KKU100, and KKU213A cell viability."	( Microalga Chlorella sp. extract induced apoptotic cell death of cholangiocarcinoma via AKT/mTOR signaling pathway. Duangjan, K; Jantakee, K; Panwong, S; Panya, A; Pekkoh, J; Sawasdee, N; Wathikthinnakon, M; Yenchitsomanus, PT, 2023)	1.63
"Gallic acid treatment improved these scores."	( Effects of gallic acid on gingival wounds. Deveci, B; Tekin, GG, 2023)	2.02
"Gallic acid treatment significantly lowered plasma levels of the creatinine and blood urea nitrogen and elevated the levels of the protein and albumin."	( Gallic acid attenuates type I diabetic nephropathy in rats. Garud, MS; Kulkarni, YA, 2018)	2.64
"Gallic acid derivative treatment significantly reduced lung histological changes and decreased inflammatory cell infiltration."	( A novel Gallic acid derivative attenuates BLM-induced pulmonary fibrosis in mice. Cao, B; Chen, H; Chen, Y; Li, W; Liu, B; Liu, T; Liu, Y; Rong, Y, 2018)	1.64
"Gallic acid pretreatment attenuated concentric cardiac hypertrophy."	( Gallic acid prevents isoproterenol-induced cardiac hypertrophy and fibrosis through regulation of JNK2 signaling and Smad3 binding activity. Cho, JY; Choi, SY; Jeong, MH; Jin, L; Kee, HJ; Kim, GR; Lin, MQ; Piao, ZH; Ryu, Y, 2016)	2.6
"Gallic acid treatment showed protective effects in these parameters evaluated, and also prevented a decrease in the activity of catalase and glutathione S-transferase, and vitamin C levels in the liver of diabetic rats."	( Effects of gallic acid on delta - aminolevulinic dehydratase activity and in the biochemical, histological and oxidative stress parameters in the liver and kidney of diabetic rats. Baldissareli, J; Chitolina Schetinger, MR; da Costa Krewer, C; da Silva Pereira, A; de Oliveira, JS; de Oliveira, LS; Lopes, TF; Morsch, VM; Reichert, KP; Spanevello, RM; Thomé, GR, 2016)	1.55
"Gallic acid treatment significantly attenuated these alterations and decreased the levels of AgNORs and PCNA."	( Antiproliferative potential of gallic acid against diethylnitrosamine-induced rat hepatocellular carcinoma. Anandakumar, P; Devaki, T; Jagan, S; Kamaraj, S; Ramakrishnan, G, 2008)	1.35
"Gallic acid pretreatment showed significant protective effect on all the biochemical parameters studied."	( Cardioprotective effect of gallic acid on cardiac troponin-T, cardiac marker enzymes, lipid peroxidation products and antioxidants in experimentally induced myocardial infarction in Wistar rats. Prince, PS; Priscilla, DH, 2009)	1.37
"Gallic acid treatment repressed Akt/ERK-mediated c-Fos phosphorylation and JNK1-mediated ATF-2 phosphorylation."	( Gallic acid downregulates matrix metalloproteinase-2 (MMP-2) and MMP-9 in human leukemia cells with expressed Bcr/Abl. Chang, LS; Chen, YJ, 2012)	2.54
"Gallic acid treatment partly restored this decreased paraoxonase activity, which resulted from ethanol administration."	( Investigation of the possible protective role of gallic acid on paraoxanase and arylesterase activities in livers of rats with acute alcohol intoxication. Bayramoğlu, G; Canbek, M; Kanbak, G; Kartkaya, K; Oğlakçi, A; Şentürk, H, 2013)	1.37
"Gallic acid treatment at the concentrations that do not affect cell viability (0.1 and 1 μM) induced cellular apoptosis of RA FLS."	( Gallic acid, a natural polyphenolic acid, induces apoptosis and inhibits proinflammatory gene expressions in rheumatoid arthritis fibroblast-like synoviocytes. Chung, SJ; Lee, SK; Lee, SW; Park, MC; Park, YB; Yoon, CH, 2013)	2.55
"Gallic acid treatment was found to induce apoptosis of RA FLS through regulation of apoptosis-related protein expressions and to reduce the expression of pro-inflammatory genes in RA FLS. "	( Gallic acid, a natural polyphenolic acid, induces apoptosis and inhibits proinflammatory gene expressions in rheumatoid arthritis fibroblast-like synoviocytes. Chung, SJ; Lee, SK; Lee, SW; Park, MC; Park, YB; Yoon, CH, 2013)	3.28
"Gallic acid treatment of DU145 cells resulted in a strong cell growth inhibition, cell cycle arrest, and apoptotic death in a dose- and time-dependent manner, together with a decrease in cyclin-dependent kinases and cyclins but strong induction in Cip1/p21."	( Gallic acid causes inactivating phosphorylation of cdc25A/cdc25C-cdc2 via ATM-Chk2 activation, leading to cell cycle arrest, and induces apoptosis in human prostate carcinoma DU145 cells. Agarwal, C; Agarwal, R; Tyagi, A, 2006)	2.5
"Treatment with gallic acid resulted in a significant reduction in proliferation and induction of apoptosis, only in EGFR-mutant NSCLC cells."	( Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover. Nam, B; Rho, JK; Shin, DM; Son, J, 2016)	2.22
"Pretreatment with gallic acid and lithium prevented hyperlocomotion and brain oxidative damage."	( Gallic acid protects cerebral cortex, hippocampus, and striatum against oxidative damage and cholinergic dysfunction in an experimental model of manic-like behavior: Comparison with lithium effects. Bona, NP; de Mattos, BDS; Gamaro, GD; Pedra, NS; Recart, VM; Soares, MSP; Spanevello, R; Spohr, L; Stefanello, F; Teixeira, FC, 2021)	2.39
"Co-treatment with gallic acid preserved all these changes approximately to the normal levels."	( Gallic acid suppresses inflammation and oxidative stress through modulating Nrf2-HO-1-NF-κB signaling pathways in elastase-induced emphysema in rats. Badavi, M; Dianat, M; Mard, SA; Radan, M; Sohrabi, F, 2021)	2.39
"The treatment with gallic acid showed significant ameliorations in abnormalities of fluoxetine-induced liver injury as represented by the improvement of hepatic CAT, SOD activities, vitamin C levels, serum biochemical parameters, and histopathological changes, in addition to the recovery of antioxidant defense system status."	( Anti-inflammatory and ameliorative effects of gallic acid on fluoxetine-induced oxidative stress and liver damage in rats. Amini, SA; Heidarian, E; Karimi-Khouzani, O, 2017)	1.03
"Treatment with gallic acid as well as fruit juice of E."	( Suppression of abdominal fat and anti-hyperlipidemic potential of Emblica officinalis: Upregulation of PPARs and identification of active moiety. Bakrania, AK; Chen, Y; Han, J; Patel, SS; Variya, BC, 2018)	0.82
"Pre-treatment with gallic acid suppressed lipid peroxidation in erythrocytes in a dose-dependent manner."	( In vivo protective effects of gallic acid isolated from Peltiphyllum peltatum against sodium fluoride-induced oxidative stress in rat erythrocytes. Daglia, M; Habtemariam, S; Hajizadeh Moghaddam, A; Nabavi, SF; Nabavi, SM; Sureda, A, 2013)	1
"Treatment with gallic acid led to the accumulation of ubiquitinated protein aggregates and the reduction in chymotrypsin-like proteasome activities indicating proteasome inhibition."	( Gallic acid protects against endothelial injury by restoring the depletion of DNA methyltransferase 1 and inhibiting proteasome activities. Chan, K; Kam, A; Li, GQ; Li, KM; Nammi, S; Razmovski-Naumovski, V, 2014)	2.18
"Pretreatment with gallic acid and famotidine in combinations for 7 days, protected the gastric mucosa significantly (p<0.05, 0.01), which was evidenced by decrease in ulcer index, gastric juice volume, free and total acidity, total protein, pepsin and DNA content, and increase in pH, carbohydrates concentration in gastric juice. "	( Synergistic effect of the combination of gallic acid and famotidine in protection of rat gastric mucosa. Asokkumar, K; Sen, S; Sivashanmugam, AT; Subhadradevi, V; Umamaheswari, M, 2014)	1
"Pre—treatment of gallic acid and mitochondrially targeted gallic acid to sodium nitroprusside treated mitochondria not only significantly reduced the oxidative stress but also prevented mitochondrial permeability pore transition to a significant difference."	( Efficiency of mitochondrially targeted gallic acid in reducing brain mitochondrial oxidative damage. Ghafourifar, P; Jat, D; Parihar, MS; Parihar, P, 2014)	1
"Treatment with gallic acid was observed to significantly mitigate SCI-induced oxidative stress and the inflammatory response by reducing the oxidative stress, decreasing the expression of NF-κB and COX-2 as well as increasing the antioxidant status of cells."	( Protective effects of gallic acid against spinal cord injury-induced oxidative stress. Wang, R; Wang, Z; Yang, YH; Zheng, J, 2015)	1.07
"Treatment with gallic acid, EGFR inhibitor, or Src inhibitor reduced DNA looping."	( Gallic acid abolishes the EGFR/Src/Akt/Erk-mediated expression of matrix metalloproteinase-9 in MCF-7 breast cancer cells. Chang, LS; Chen, YJ; Huang, CH; Jhang, LM; Lee, YC; Lin, KN, 2016)	2.22
"Treatment with gallic acid methyl ester (12.5 and 50 microM) or PGG (3.125, 12.5 and 50 microM) reduced hepatocyte necrosis induced by tert-butyl hydroperoxide."	( 1,2,3,4,6-penta-O-galloyl-beta-D-glucose from Galla Rhois protects primary rat hepatocytes from necrosis and apoptosis. An, RB; Kim, YC; Park, EJ; Sohn, DH; Zhao, YZ, 2008)	0.69
"Pretreatment with gallic acid (15 mg/kg) to isoproterenol treated rats significantly (P<0.05) prevented the changes in the activities of cardiac marker enzymes, the levels of lipid peroxidation products, reduced glutathione and the activities of lysosomal enzymes."	( Gallic acid prevents lysosomal damage in isoproterenol induced cardiotoxicity in Wistar rats. Devika, PT; Priscilla, H; Stanely Mainzen Prince, P, 2009)	2.12
"Oral treatment with gallic acid (10 and 20mg/kg) daily for a period of 21days showed significant (P<0.05) protective effects on all the biochemical parameters studied."	( Antihyperglycaemic, antilipid peroxidative and antioxidant effects of gallic acid on streptozotocin induced diabetic Wistar rats. Kumar, R; Prince, PS; Punithavathi, VR; Selvakumari, J, 2011)	0.92
"Oral treatment with gallic acid (10 mg and 20 mg/kg) for 21 days significantly decreased the levels of blood glucose, brain lipid peroxidation products, and lipids and significantly increased the activities of brain enzymic antioxidants in diabetic rats."	( Effects of gallic acid on brain lipid peroxide and lipid metabolism in streptozotocin-induced diabetic Wistar rats. Kumar, MR; Selvakumari, CJ; Stanely Mainzen Prince, P, )	0.84
"Co-treatment of gallic acid significantly prevented the lindane induced alterations in kidney and liver tissues with a decrease in LPO, serum marker enzyme activity and a significant increase in antioxidant levels."	( Protective effect of gallic acid against lindane induced toxicity in experimental rats. Arun Felix, T; Baskaran, R; Poornima, P; Sowmya, P; Vijaya Padma, V, 2011)	1.02
"Pretreatment with gallic acid at 20 mg/kg was exhibited significant reduction in the thiobarbituric acid reactive substances level (37.06 ± 1.4 nmol MDA eq/g tissue, p > 0.05 vs."	( Protective role of gallic acid on sodium fluoride induced oxidative stress in rat brain. Habtemariam, S; Jafari, M; Nabavi, SF; Nabavi, SM; Sureda, A, 2012)	1.03
"Pretreatment with gallic acid (1-10 microM) significantly attenuated the relaxation induced by acetylcholine, and that with 10 microM gallic acid also reduced the potency of sodium nitroprusside in the relaxation, without a reduction in efficacy, in endothelium-denuded arteries."	( Endothelium-dependent contraction of rat thoracic aorta induced by gallic acid. Hayashi, H; Miyaichi, Y; Sanae, F, 2003)	0.88
"Pre-treatment with gallic acid significantly rendered K562 cells more susceptible to NK cell-mediated necrosis, while pre-treatment with rutin significantly rendered K562 cells more susceptible to apoptosis."	( Effect of phenols on natural killer (NK) cell-mediated death in the K562 human leukemic cell line. Andrikopoulos, NK; Dedoussis, GV; Kaliora, AC, 2005)	0.65
"Pretreatment of gallic acid inhibited 10 microM Abeta (25-35)-induced elevation of cytosolic Ca(2+) concentration ([Ca(2+)](c)) and generation of reactive oxygen species (ROS), which were measured by fluorescent dyes."	( Neuroprotective properties of gallic acid from Sanguisorbae radix on amyloid beta protein (25--35)-induced toxicity in cultured rat cortical neurons. Bae, K; Ban, JY; Cho, SO; Ju, HS; Kim, JY; Lee, HJ; Nguyen, HT; Seong, YH; Song, KS, 2008)	0.97

Excerpt	Reference	Relevance
" Bismuth blood and urine levels obtained from patients after administration of a new anti-ulcer drug (Bicitropeptide) in a well controlled clinical trial are discussed and suggest that that this bismuth containing drug behaves pharmacologically in a manner similar to the inorganic bismuth salts in man, low bismuth blood levels and the absence of toxic side effects being conspicuous features of the drug."	( Bismuth toxicity in man II. Review of bismuth blood and urine levels in patients after administration of therapeutic bismuth formulations in relation to the problem of bismuth toxicity in man. Mekel, R; Serfontein, WJ, 1979)	0.26
" In conclusion, gallic acid-induced cytotoxicity in mouse spermatogonia, mouse spermatocytes, and mouse Sertoli cells in vitro may be of toxicological research interest considering the testicular toxic potential of gallic acid."	( Cytotoxic effect of gallic acid on testicular cell lines with increasing H2O2 level in GC-1 spg cells. Chang, MS; Choi, HY; Kim, DR; Kim, H; Park, EH; Park, SK; Park, W; Yang, WM, 2008)	1.02
" There were no dose-related adverse events or differences between groups in uterine size, food intake, corpora lutea, implantations, litter size, number of live fetuses, and gender distribution of fetuses or fetal resorptions."	( Oral dose-ranging developmental toxicity study of an herbal supplement (NT) and gallic acid in rats. Amen, RJ; Booth, A; Greenway, FL; Scott, M, 2010)	0.59
"Lindane is an organochlorine pesticide that persists in the environment, bioaccumulate through food chain and has a risk of causing adverse effects to human health and the environment."	( Protective effect of gallic acid against lindane induced toxicity in experimental rats. Arun Felix, T; Baskaran, R; Poornima, P; Sowmya, P; Vijaya Padma, V, 2011)	0.69
" It was observed that C(14) decreased lung metastasis in vivo by 80% and increased the survival rate of the animals without toxic effects."	( Antimetastatic activity and low systemic toxicity of tetradecyl gallate in a preclinical melanoma mouse model. Carvalho, DR; Creczynski-Pasa, TB; de Cordova, CA; Locatelli, C; Mascarello, A; Nunes, RJ; Pilati, C; Yunes, RA, 2012)	0.38
"The present study assessed the toxic effects of stable aqueous colloidal suspensions of gallic-acid-stabilized C(70) fullerene on Daphnia magna."	( Toxicity of aqueous C70-gallic acid suspension in Daphnia magna. Ke, PC; Klaine, SJ; Mount, AS; Seda, BC, 2012)	0.69
" Prefibrillar species were more toxic than mature fibrils."	( Dendrimers reduce toxicity of Aβ 1-28 peptide during aggregation and accelerate fibril formation. Correa, J; Fernandez-Megia, E; Fernandez-Villamarin, M; Ionov, M; Klajnert, B; Riguera, R; Sousa-Herves, A; Wasiak, T, 2012)	0.38
"5 up to 125 μM without any adverse effect."	( Protective effects of the key compounds isolated from Corni fructus against β-amyloid-induced neurotoxicity in PC12 cells. Hong, SY; Jeong, WS; Jun, M, 2012)	0.38
" Preventing the initial aggregation event of IAPP is one strategy for slowing, and possibly preventing, the toxic effects of IAPP oligomeric intermediates."	( IAPP aggregation and cellular toxicity are inhibited by 1,2,3,4,6-penta-O-galloyl-β-D-glucose. Bruno, E; Kao, PY; Moffet, DA; Nogaj, LA; Pereira, C; Roman, KP; Takiguchi, M, 2013)	0.39
") leaf extract or ethyl gallate could be used as potential antioxidants with safe therapeutic application in cancer chemotherapy."	( In vitro protection of biological macromolecules against oxidative stress and in vivo toxicity evaluation of Acacia nilotica (L.) and ethyl gallate in rats. Arul, J; Chandrasekaran, R; Mohan, S; Thiagarajan, K, 2014)	0.4
" Gallic acid was practically non-toxic (96-h lethal concentration (LC50) > 100 mg/L) whereas pelargonic acid was slightly toxic (96-h LC50 of 81."	( Acute toxicity and sublethal effects of gallic and pelargonic acids on the zebrafish Danio rerio. Fontaine, P; Milla, S; Techer, D; Thomas, M; Viot, S, 2015)	1.33
"Cyclophosphamide (CPA) is a widely used anticancer chemotherapeutic agent and its toxicity has been associated with its toxic metabolites phosphormide mustard."	( Gallic Acid Ameliorates Cyclophosphamide-Induced Neurotoxicity in Wistar Rats Through Free Radical Scavenging Activity and Improvement in Antioxidant Defense System. Akinrinde, AS; Dada, RO; Olowu, ER; Omobowale, TO; Oyagbemi, AA; Saba, AB, 2016)	1.88
" Single dosing of NADPH or omitting toxic components from the MAS preparation did also not reduce embryotoxicity."	( Antioxidants reduce reactive oxygen species but not embryotoxicity in the metabolic Danio rerio test (mDarT). Bars, C; Knapen, D; Pype, C; Saad, MA; Van Cruchten, SJ; Van Ginneken, CJ; Verbueken, E, 2017)	0.46
"The major side effect of gentamicin (GEN) is nephrotoxicity which in turn restricts the clinical use of this drug."	( Ameliorative effects of gallic acid on gentamicin-induced nephrotoxicity in rats. Fatemi, I; Ghaznavi, H; Gholamine, B; Goudarzi, M; Hosseini Tabatabaei, SMT; Kalantar, M; Kalantari, H; Mehrabani, M; Mehrzadi, S, 2018)	0.79
" Over all the results of acute and subacute toxicity studies conclude that oral administration of TCF, TAB and 7MG were observed to be relatively non-toxic and affords practical guidance for selecting safe dose for further clinical trials."	( Safety assessment of methanolic extract of Terminalia chebula fruit, Terminalia arjuna bark and its bioactive constituent 7-methyl gallic acid: In vitro and in vivo studies. Archunan, G; Muniasamy, S; Suganthy, N, 2018)	0.69
" The QUIN is involved in the development of several toxic cascades which leads to the neuronal degeneration processes."	( Effect of wedelolactone and gallic acid on quinolinic acid-induced neurotoxicity and impaired motor function: significance to sporadic amyotrophic lateral sclerosis. Goli, D; S, M; T, P, 2018)	0.77
"Arsenic is an important toxic chemical affecting millions of people around the world."	( Ameliorative effect of gallic acid on sodium arsenite-induced spleno-, cardio- and hemato-toxicity in rats. Goudarzi, M; Hosseinzadeh, A; Houshmand, G; Kalantar, M; Mansouri, E; Mehrzadi, S; Sezavar, SH, 2019)	0.82
"Chronic exposure to toxic inorganic arsenic results in the adverse health effects including skin lesions, cardiovascular diseases, diabetes, neurological disorders, and liver and kidney diseases."	( Gallic acid ameliorates sodium arsenite-induced renal and hepatic toxicity in rats. Gholamine, B; Goudarzi, M; Hosseinzadeh, A; Houshmand, G; Kalantar, M; Mehrzadi, S, 2021)	2.06
" Results indicated that gallic and ferulic acids can exert toxic effects on in vitro cell models at high concentrations, suggesting that an excessive and uncontrolled consumption of polyphenols may induce negative effects on the intestinal wall."	( Are Supplements Safe? Effects of Gallic and Ferulic Acids on In Vitro Cell Models. Abduazizova, V; Dinelli, G; Spisni, E; Tibaldi, C; Truzzi, F; Valerii, MC; Zhang, Y, 2020)	0.56
"Mitochondria are the main target organelles through which drugs and chemicals exert their toxic effect on cardiomyocytes."	( Gallic acid inhibits celecoxib-induced mitochondrial permeability transition and reduces its toxicity in isolated cardiomyocytes and mitochondria. Atashbar, S; Salimi, A; Shabani, M, 2021)	2.06
" The macrophage lineage cytotoxicity assay showed that the chloroform fraction was more toxic than the acetate fraction."	( Molecular docking studies and evaluation of the antiretroviral activity and cytotoxicity of the species Lafoensia pacari Saint-Hilaire. Araújo, MV; Bento, ES; Costa, JGD; Cunha, AL; Ferreira, RCS; Fonseca, SA; Lima, FCA; Moreira, MSA; Rocha, TJM; Sabino, AR; Santana, AEG; Santos, AF; Silva, KWL; Silva, MSCE, 2022)	0.72
" Simultaneously, no toxicity was detected after acute or subacute treatment of KFWD, providing valuable evidence for the traditional safe use of KF."	( Kochiae Fructus: Evaluation on the antioxidant properties and oral safety of its water decoction. Chen, XL; Han, M; Li, B; Li, LH; Wang, HL; Zhang, K; Zhang, YM; Zhao, X, 2022)	0.72

Excerpt	Reference	Relevance
" Concentrations of GA and its metabolite, 4-O-methylgallic acid (4OMGA), were determined, and the pharmacokinetic parameters were calculated."	( Pharmacokinetics of gallic acid and its relative bioavailability from tea in healthy humans. Aoyagi, K; Bitsch, I; Koyama, A; Shahrzad, S; Winter, A, 2001)	0.88
" So the pharmacokinetic parameters were calculated out."	( [Study on the pharmacokinetics and bioavailability of syringic acid in rabbits]. Guo, X; Liu, Y; Lü, Z; Xie, W, 2003)	0.32
" The validated HPLC-MS/MS method was successfully applied to the pharmacokinetic study in rats following oral administration of leonurine."	( Quantification of leonurine, a novel potential cardiovascular agent, in rat plasma by liquid chromatography-tandem mass spectrometry and its application to pharmacokinetic study in rats. Cai, W; Ma, G; Sha, X; Shi, X; Zheng, Y; Zhu, Q; Zhu, Y, 2012)	0.38
"The purpose of this study was to investigate the potential pharmacokinetic interactions with natural products (such as piperine (PIP), gallic acid (GA) and cinnamic acid (CA)) and rosuvastatin (RSV) (a specific breast cancer resistance protein, BCRP substrate) in rats."	( Effects of piperine, cinnamic acid and gallic acid on rosuvastatin pharmacokinetics in rats. Basu, S; Jana, S; Patel, H; Patel, VB, 2013)	0.86
" The results demonstrated that the present LC-MS/MS method was sensitive enough for pharmacokinetic study of stachydrine and leonurine following oral administration of Herba Leonuri extract."	( Simultaneous determination and pharmacokinetic study of stachydrine and leonurine in rat plasma after oral administration of Herba Leonuri extract by LC-MS/MS. Li, B; Li, X; Wu, J, 2013)	0.39
" Cmax and AUC of gallic acid were increased (P<0."	( Influence of processing on pharmacokinetic of typical constituents in radix polygoni multiflori after oral administration by LC-ESI-MS/MS. Chang, YX; Gao, XM; He, J; Li, J; Ma, WF; Zhang, BL; Zhang, L; Zhang, P; Zheng, F, 2013)	0.73
" The LC-MS/MS method could be used to evaluate the effect of processing on pharmacokinetic of typical constituents in radix polygoni multiflori after oral administration."	( Influence of processing on pharmacokinetic of typical constituents in radix polygoni multiflori after oral administration by LC-ESI-MS/MS. Chang, YX; Gao, XM; He, J; Li, J; Ma, WF; Zhang, BL; Zhang, L; Zhang, P; Zheng, F, 2013)	0.39
" The main pharmacokinetic parameters of GA and PCA were obtained based on the analysis of the plasma sample by non-compartmental analysis."	( An UHPLC-MS/MS method for simultaneous quantification of gallic acid and protocatechuic acid in rat plasma after oral administration of Polygonum capitatum extract and its application to pharmacokinetics. Gong, X; Li, M; Ma, F; Zhao, Y; Zhou, X, 2015)	0.66
" Pharmacokinetic parameters for GA and PCA following oral administration of the extract were respectively: Cmax 246."	( An UHPLC-MS/MS method for simultaneous quantification of gallic acid and protocatechuic acid in rat plasma after oral administration of Polygonum capitatum extract and its application to pharmacokinetics. Gong, X; Li, M; Ma, F; Zhao, Y; Zhou, X, 2015)	0.66
" capitatum extract may be metabolized to GA, which affected the pharmacokinetic profiles of GA."	( An UHPLC-MS/MS method for simultaneous quantification of gallic acid and protocatechuic acid in rat plasma after oral administration of Polygonum capitatum extract and its application to pharmacokinetics. Gong, X; Li, M; Ma, F; Zhao, Y; Zhou, X, 2015)	0.66
" However, knowledge concerning the pharmacokinetic characteristics of MG and PGG is limited."	( A validated liquid chromatography-tandem mass spectrometry method for the determination of methyl gallate and pentagalloyl glucopyranose: application to pharmacokinetic studies. Bavovada, R; Gao, S; Hu, M; Jiamboonsri, P; Pithayanukul, P, 2015)	0.42
" Due to the low exposure of the five main medicative ingredients (amygdalin, cinnamic acid, gallic acid, paeoniflorin and paeonol) of GZFL in human, a strategy was built to qualitatively and quantitatively identify the possible metabolites of GZFL and to describe the pharmacokinetic profiles of GZFL in human."	( Integrated identification, qualification and quantification strategy for pharmacokinetic profile study of Guizhi Fuling capsule in healthy volunteers. Aa, JY; Gu, SY; Jin, XL; Ou-Yang, BC; Peng, Y; Sun, JG; Wang, GJ; Wang, Y; Wang, ZZ; Xiao, W; Zhang, KR; Zhong, YX, 2016)	0.65
"05) in the pharmacokinetic parameters between the primary dysmenorrhoea and normal groups."	( Comparative pharmacokinetics study of leonurine and stachydrine in normal rats and rats with cold-stagnation and blood-stasis primary dysmenorrhoea after the administration of Leonurus japonicus houtt electuary. Gong, LY; Kamara, MO; Ma, HY; Meng, FH; Sun, Q; Wang, L; Wen, YQ; Zhao, N, 2019)	0.51
" Whereas, the pharmacokinetic was conducted in rats by administering either MAR alone or combined with MG through oral and/or intravenous routes."	( Evaluation of the pharmacokinetic-pharmacodynamic integration of marbofloxacin in combination with methyl gallate against Salmonella Typhimurium in rats. Birhanu, BT; Lee, EB; Park, SC, 2020)	0.56
"GA and PCA were absorbed into the blood within 1 h after administration and rapidly eliminated with a half-life of less than 2 h."	( Pharmacokinetics of gallic acid and protocatechuic acid in humans after dosing with Relinqing (RLQ) and the potential for RLQ-perpetrated drug-drug interactions on organic anion transporter (OAT) 1/3. Cao, Y; Du, X; Huang, Y; Li, Y; Li, Z; Liu, C; Sun, J; Wang, B; Wang, R; Wu, W, 2021)	0.94
"GA and PCA are recommended as PK-markers in RLQ-related pharmacokinetic and drug interaction studies."	( Pharmacokinetics of gallic acid and protocatechuic acid in humans after dosing with Relinqing (RLQ) and the potential for RLQ-perpetrated drug-drug interactions on organic anion transporter (OAT) 1/3. Cao, Y; Du, X; Huang, Y; Li, Y; Li, Z; Liu, C; Sun, J; Wang, B; Wang, R; Wu, W, 2021)	0.94
" However, the pharmacokinetic and target tissue distribution data of QLP are still unknown."	( Simultaneous determination of multiple constituents of Qi-Lin pill by UPLC-MS/MS: Applications to pharmacokinetics and testicular tissue distribution in rats. Dai, Y; Fan, CL; Li, RX; Li, ZT; Su, ZJ; Tang, XY; Wang, XX; Wei, W; Xu, WY; Yao, ZH; Zhao, PC, 2023)	0.91

Excerpt	Reference	Relevance
" ESR spectroscopy might be applicable for the detection of drug-drug interaction."	( [Detection of drug-drug interaction by ESR spectroscopy]. Sakagami, H; Satoh, K, 1999)	0.3
" This study investigated the antibacterial activities of nalidixic acid in combination with methyl gallate and carvacrol against nalidixic acid resistant bacteria."	( Antibacterial activity of methyl gallate isolated from Galla Rhois or carvacrol combined with nalidixic acid against nalidixic acid resistant bacteria. Chae, HS; Choi, JG; Jang, HJ; Kang, OH; Kwon, DY; Lee, YS; Oh, YC; Shin, DW, 2009)	0.35
"The antimicrobial activities of tetracycline, mupirocin, and fusidic acid are tested in combination with Epicatechin Gallate (ECG), and Ethyl Gallate (EG) using 2 Methicillin resistant (MRSA) and 2 Methicillin sensitive (MSSA) strains of Staphylococcus aureus."	( In vitro drug interactions of gallates with antibiotics in Staphylococcus Aureus. Chu Sing Lim, L; Sakharkar, KR; Sakharkar, MK; Soe, WM; Tzer Pin Lin, R, 2010)	0.36
"To study the anti-cataract effect of gigantol combined with syringic acid and their action mechanism."	( [Study on anti-cataract effect of gigantol combined with syringic acid and their mechanism]. Diao, H; Fang, H; Gao, X; Gu, L; Gu, Q; Qi, H; Wang, L; Wang, Z; Wei, X; Yi, Y, 2012)	0.38
"H202-induced lens oxidative injury in vitro rat model was establish to observe the impact of gigantol combined with syringic acid on lens transparency under a dissecting microscope."	( [Study on anti-cataract effect of gigantol combined with syringic acid and their mechanism]. Diao, H; Fang, H; Gao, X; Gu, L; Gu, Q; Qi, H; Wang, L; Wang, Z; Wei, X; Yi, Y, 2012)	0.38
"Gigantol combined with syringic acid shows good anti-cataract, their action mechanism is reflected in their good collaborative inhibitory effect on AR."	( [Study on anti-cataract effect of gigantol combined with syringic acid and their mechanism]. Diao, H; Fang, H; Gao, X; Gu, L; Gu, Q; Qi, H; Wang, L; Wang, Z; Wei, X; Yi, Y, 2012)	0.38
" In combination with tannins, antibiotics showed increased MICs, suggesting that tannins interfered with antibacterial activity."	( Effect of tannic and gallic acids alone or in combination with carbenicillin or tetracycline on Chromobacterium violaceum CV026 growth, motility, and biofilm formation. Dusane, DH; O'May, C; Tufenkji, N, 2015)	0.74
"A simple, rapid and reliable microwave-assisted extraction (MAE) combined with ultra performance liquid chromatography tandem mass spectrometry method was developed for simultaneous determination of the seven bioactive constituents in Guizhi Fuling capsule (GFC), namely gallic acid, amygdalin, albiflorin, paeoniflorin, paeonol, cinnamic acid and pachymic acid, respectively."	( Simultaneous determination of seven bioactive components in Guizhi Fuling capsule by microwave-assisted extraction combined with ultra performance liquid chromatography tandem mass spectrometry. Sui, Y; Wang, ZZ; Xiao, W; Xiong, ZL; Zhao, LS; Zhao, YT, 2016)	0.61
"The aim of this study was to: (a) develop a simple, high performance thin layer chromatographic (HPTLC) method combined with direct 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay to rapidly assess and compare free radical scavenging activity or anti-oxidant activity for major classes of polyphenolics present in wines; and (b) to investigate relationship between free radical scavenging activity to the total polyphenolic content (TPC) and total antioxidant capacity (TAC) in the wine samples."	( Development and validation of a simple high performance thin layer chromatography method combined with direct 1,1-diphenyl-2-picrylhydrazyl assay to quantify free radical scavenging activity in wine. Agatonovic-Kustrin, S; Morton, DW; Yusof, AP, 2016)	0.43
" Combined with retention time, accurate mass, characteristic fragments and previous literature data, the structures of the filtered compounds were identified or tentatively characterized."	( [Rapid analysis on phenolic compounds in Rheum palmatum based on UPLC-Q-TOF/MSE combined with diagnostic ions filter]. Fu, S; Gao, XY; Huang, ZH; Liu, YH; Lu, ZW; Wang, ML; Wang, Q; Xie, ZY; Yu, HH; Zhang, QQ; Zhang, ZX; Zhao, HZ; Zhou, WJ, 2017)	0.46
" To increase its yield of arachidonic acid, heavy ion beam irradiation mutagenesis of Mortierella alpina was carried out in combination with triclosan and octyl gallate treatment."	( Heavy ion mutagenesis combined with triclosan screening provides a new strategy for improving the arachidonic acid yield in Mortierella alpina. Cui, Q; Feng, Y; Li, X; Lu, D; Song, X; Zhang, H, 2018)	0.48
" In this present study, we demonstrated that as-prepared gallic acid (GA) coated reduced graphene oxide (rGO) combined with radiofrequency (RF) ablation has facilitated for the treatment of human renal epithelial cancer (A-489) cells without disturbing the renal proximal epithelial (HK-2) cells."	( Effects of gallic acid biofabricated rGO nanosheets combined with radiofrequency radiation for the treatment of renal cell carcinoma. Chen, C; Guo, Z; Jiang, Z; Jin, H; Liu, X; Sun, S; Zhang, J, 2018)	1.12
" Furthermore, MG alone or in combination with sub-MIC of MRB decreased the motility of Salmonella Typhimurium."	( Inhibition of Salmonella Typhimurium adhesion, invasion, and intracellular survival via treatment with methyl gallate alone and in combination with marbofloxacin. Birhanu, BT; Hossain, MA; Lee, SJ; Park, NH; Park, SC, 2018)	0.48
" No data are available about the efficacy of CHA and GA combined with azoles on the antifungal susceptibility and on the virulence of both fungi."	( Effect of chlorogenic and gallic acids combined with azoles on antifungal susceptibility and virulence of multidrug-resistant Candida spp. and Malassezia furfur isolates. Aneke, CI; Annoscia, G; Boekhout, T; Cafarchia, C; Otranto, D; Rhimi, W, 2020)	0.86
" Whereas, the pharmacokinetic was conducted in rats by administering either MAR alone or combined with MG through oral and/or intravenous routes."	( Evaluation of the pharmacokinetic-pharmacodynamic integration of marbofloxacin in combination with methyl gallate against Salmonella Typhimurium in rats. Birhanu, BT; Lee, EB; Park, SC, 2020)	0.56
"Relinqing granules (RLQ) are being used alone or in combination with antibacterial drugs to treat urological disorders."	( Pharmacokinetics of gallic acid and protocatechuic acid in humans after dosing with Relinqing (RLQ) and the potential for RLQ-perpetrated drug-drug interactions on organic anion transporter (OAT) 1/3. Cao, Y; Du, X; Huang, Y; Li, Y; Li, Z; Liu, C; Sun, J; Wang, B; Wang, R; Wu, W, 2021)	0.94
"To verify synergistic effects, we investigated the antimicrobial activity of seven phenolic phytochemicals (gallic acid; epicatechin; epigallocatechin gallate; daidzein; genistein; myricetin; 3-hydroxy-6-methoxyflavone) in combination with six antibiotics against multidrug-resistant isolates from the ESKAPE group."	( Synergistic antimicrobial activities of epigallocatechin gallate, myricetin, daidzein, gallic acid, epicatechin, 3-hydroxy-6-methoxyflavone and genistein combined with antibiotics against ESKAPE pathogens. Borchardt, J; Böttcher, I; Buchmann, D; Guenther, S; Schaufler, K; Schultze, N, 2022)	1.16
"The aim of this study is to demonstrate the potential use of phenolic natural compounds in combination with conventional antibiotics against multidrug-resistant bacteria of the ESKAPE group."	( Synergistic antimicrobial activities of epigallocatechin gallate, myricetin, daidzein, gallic acid, epicatechin, 3-hydroxy-6-methoxyflavone and genistein combined with antibiotics against ESKAPE pathogens. Borchardt, J; Böttcher, I; Buchmann, D; Guenther, S; Schaufler, K; Schultze, N, 2022)	0.94
" The juice was combined with the six abovementioned antioxidants at different concentrations, then treated by HHP at 550 MPa/10 min/25 °C and stored at 4 °C for 20 days."	( Effects of different antioxidants combined with high hydrostatic pressure on the color and anthocyanin retention of a blueberry juice blend during storage. Bi, X; Che, Z; Li, J; Li, M; Ning, N; Wang, X; Wang, Y; Xing, Y, 2023)	0.91
"The effect of gallic acid alkyl esters and their combination with monoacylglycerol (MAG) and 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) on the formation of hydroperoxides and hexanal were determined during the oxidation of stripped soybean oil."	( Interfacial behavior of gallic acid and its alkyl esters in stripped soybean oil in combination with monoacylglycerol and phospholipid. Ahmadi Gavlighi, H; Barba, FJ; Barzegar, M; Delfanian, M; Sahari, MA, 2023)	1.58

Excerpt	Reference	Relevance
"Glucoconjugates of (+/-)-ibuprofen, (+/-)-alpha-tocopherol (vitamin E), gentisic acid, gallic acid, 2,6-bis(tert-butyl)-4-thiophenol, and N-acetyl-L-cysteine were prepared with the objective of increasing the bioavailability of such antioxidant and anti-inflammatory drugs."	( Synthesis of antioxidative and anti-inflammatory drugs glucoconjugates. Beyreuther, K; Picard, MA; Uhrig, RK; Wiessler, M, 2000)	0.53
" Thus, the therapeutic efficacy of oral administration at the various doses of eugeniin was similar to that of intraperitoneal administration, suggesting that the oral bioavailability of eugeniin was high with respect to absorption."	( Biological characterization of eugeniin as an anti-herpes simplex virus type 1 compound in vitro and in vivo. Hozumi, T; Kadota, S; Kurokawa, M; Namba, T; Shiraki, K; Tsurita, M, 2001)	0.31
" We conducted a study using acidum gallicum tablets that contained 10% GA and 90% glucose and a black tea brew that contained 93% of its GA in free form to determine the pharmacokinetics and relative bioavailability of GA in healthy humans."	( Pharmacokinetics of gallic acid and its relative bioavailability from tea in healthy humans. Aoyagi, K; Bitsch, I; Koyama, A; Shahrzad, S; Winter, A, 2001)	0.63
" Our results suggested that low molecular weight polyphenols are absorbed in the intestine and metabolized to their glucuronide conjugates, which exhibit antioxidative activity in plasma, and that TA can enhance the bioavailability of wine polyphenols."	( Absorption and metabolism of antioxidative polyphenolic compounds in red wine. Harada, M; Kiso, Y; Koda, H; Sakane, T; Sezaki, H; Sugiura, N; Yamashita, S, 2002)	0.31
"Polyphenols are antioxidants, which are known to influence bioavailability of metals in the body."	( Coordination of aluminium with purpurogallin and theaflavin digallate. Astill, C; Baderschneider, B; O'Coinceanainn, M, 2003)	0.32
"To study the pharmacokinetics and bioavailability of syringic acid(SA) in rabbits by HPLC."	( [Study on the pharmacokinetics and bioavailability of syringic acid in rabbits]. Guo, X; Liu, Y; Lü, Z; Xie, W, 2003)	0.32
" By comparing the AUC of the two curves, bioavailability was obtained."	( [Study on the pharmacokinetics and bioavailability of syringic acid in rabbits]. Guo, X; Liu, Y; Lü, Z; Xie, W, 2003)	0.32
" fitted in a two-compartment open model and the absolute bioavailability was 86."	( [Study on the pharmacokinetics and bioavailability of syringic acid in rabbits]. Guo, X; Liu, Y; Lü, Z; Xie, W, 2003)	0.32
" The relative bioavailability of CA against GA was about 70."	( Intestinal absorption of p-coumaric and gallic acids in rats after oral administration. Hitomi, Y; Konishi, Y; Yoshioka, E, 2004)	0.59
" Currently, more attention is mainly focused on intestinal microflora biodegradation of tannins especially ellagitannins which can contribute to the definition of their bioavailability for both human beings and ruminants."	( Biodegradation of gallotannins and ellagitannins. Dongying, J; Kai, Y; Li, M; Qiang, H, 2006)	0.33
" The extract was also tested for its oral bioavailability by using the serum of normal rats gavaged with the extract in the assay."	( Gallic acid is partially responsible for the antiangiogenic activities of Rubus leaf extract. Greenway, FL; Lewis, J; Liu, D; Liu, Z; Schwimer, J; Woltering, EA; York, DA, 2006)	1.78
"Consumption of polyphenols is associated with health promotion through diet, although many are poorly absorbed in animals and humans alike."	( Protection of lipids from oxidation by epicatechin, trans-resveratrol, and gallic and caffeic acids in intestinal model systems. Chetrit, D; Kerem, Z; Regev-Shoshani, G; Shoseyov, O, 2006)	0.33
"The present study explored the bioavailability and brain deposition of a grape seed polyphenolic extract (GSPE) previously found to attenuate cognitive deterioration in a mouse model of Alzheimer's disease (AD)."	( Bioavailability of gallic acid and catechins from grape seed polyphenol extract is improved by repeated dosing in rats: implications for treatment in Alzheimer's disease. Cooper, B; Ferruzzi, MG; Ho, L; Janle, EM; Lobo, JK; Pasinetti, GM; Simon, JE; Weaver, C; Welch, C; Wu, QL, 2009)	0.68
"The bioavailability values observed are in agreement with previous reports, although the dosage of polyphenols ingested in this study is remarkably lower."	( Bioavailability of catechins from ready-to-drink tea. Brighenti, F; Calani, L; Cordero, C; Del Rio, D; Jechiu, L; Scazzina, F, 2010)	0.36
" However, bioavailability studies have shown low concentration of anthocyanins in plasma and urine."	( Metabolism of anthocyanins by human gut microflora and their influence on gut bacterial growth. de Pascual-Teresa, S; Hidalgo, M; Kallithraka, S; Kolida, S; Oruna-Concha, MJ; Spencer, JP; Walton, GE, 2012)	0.38
" The protective effects of SA are mediated by reducing oxidative stress and retaining the bioavailability of NO in the cardiovascular system."	( Syringic acid ameliorates (L)-NAME-induced hypertension by reducing oxidative stress. Kumar, S; Prahalathan, P; Raja, B, 2012)	0.38
"These results indicate that influence of the processing could improve the bioavailability of gallic acid and reduce the absorption of PM-SG, polydatin and emodin in rats."	( Influence of processing on pharmacokinetic of typical constituents in radix polygoni multiflori after oral administration by LC-ESI-MS/MS. Chang, YX; Gao, XM; He, J; Li, J; Ma, WF; Zhang, BL; Zhang, L; Zhang, P; Zheng, F, 2013)	0.61
" Also, the complex improved the pharmacokinetics of GA by increasing the relative bioavailability and elimination half-life."	( The gallic acid-phospholipid complex improved the antioxidant potential of gallic acid by enhancing its bioavailability. Ahammed, SM; Bhattacharyya, S; Mukherjee, PK; Saha, BP, 2013)	0.95
" However, the short lifetime and the autoxidation of GA in aqueous solution significantly reduces its bioavailability and the residence time in the body system."	( Preparation, characterization and in vitro release study of gallic acid loaded silica nanoparticles for controlled release. Feng, S; Hu, H; Nie, L; Suo, J, 2013)	0.63
" In this study, we compared the bioavailability of EGCG and O-methyl EGCGs in rats, and clarified the pharmacokinetics of O-methyl EGCGs."	( Comparison of (-)-epigallocatechin-3-O-gallate (EGCG) and O-methyl EGCG bioavailability in rats. Ichiyanagi, T; Ito, R; Ito, T; Maruki-Uchida, H; Oritani, Y; Setoguchi, Y, 2013)	0.39
" It has a good solubility and bioavailability but short half-life."	( Characterization of freeze-dried gallic acid/xyloglucan. Hirun, N; Sangfai, T; Tantishaiyakul, V, 2015)	0.7
" The efficacy of the polyphenols declined with increasing pH, indicating potential polymerization and corresponding reduced bioavailability of the polyphenols."	( Natural xenobiotics to prevent cyanobacterial and algal growth in freshwater: contrasting efficacy of tannic acid, gallic acid, and gramine. Bährs, H; Chakrabarti, S; Laue, P; Steinberg, CE, 2014)	0.61
" Our results suggest that polyphenolic compounds might be potential structural bases and source to find and project nature-based, safe, orally bioavailable direct thrombin inhibitors."	( Thrombin inhibitory activity of some polyphenolic compounds. Bijak, M; Krotkiewski, H; Nowak, P; Pawlaczyk, I; Ponczek, M; Saluk, J; Wachowicz, B; Ziewiecki, R, 2014)	0.4
" In order to increase the bioavailability of gallic acid inside the mitochondria we synthesized mitochondrially targeted gallic acid and explored its preventive effects against sodium nitroprusside induced oxidative stress in isolated mitochondria."	( Efficiency of mitochondrially targeted gallic acid in reducing brain mitochondrial oxidative damage. Ghafourifar, P; Jat, D; Parihar, MS; Parihar, P, 2014)	0.93
" In this article, a leonurine O/O microemulsion (LE-ME) was prepared and investigated for its in vivo pharmacokinetic behavior and bioavailability in the mouse body using an aqueous suspension of leonurine (LE-SWW) for the control group."	( A study on the PK and BA profiles in the mouse body for leonurine O/O microemulsion with determination by the LC-MS/MS method. Ding, Q; Lu, C; Lu, T; Sun, Y; Yuan, Y; Zhang, X, 2016)	0.43
" In depth-knowledge of the mechanisms used by tolerant microorganisms to adapt to hydroxybenzoic acids would be a step forward to improve the bioavailability of GA or select/engineer production hosts with improved metabolic traits for the bioconversion of pretreated lignocellulosic biomass."	( Molecular adaptation of Lactobacillus plantarum WCFS1 to gallic acid revealed by genome-scale transcriptomic signature and physiological analysis. de las Rivas, B; López de Felipe, F; Matesanz, R; Muñoz, R; Reverón, I, 2015)	0.66
" Therefore, this study was performed to evaluate the factors affecting their oral bioavailability as pure compounds and as components in MSKE."	( Factors Influencing Oral Bioavailability of Thai Mango Seed Kernel Extract and Its Key Phenolic Principles. Bavovada, R; Gao, S; Hu, M; Jiamboonsri, P; Leanpolchareanchai, J; Pithayanukul, P; Yin, T, 2015)	0.42
" In the present study, the effects of gallic acid and ellagic acid pretreatment on intestinal transport and oral bioavailability of metoprolol were investigated."	( Enhanced oral bioavailability of metoprolol with gallic acid and ellagic acid in male Wistar rats: involvement of CYP2D6 inhibition. Athukuri, BL; Neerati, P, 2016)	0.96
" The bioavailability study was conducted to evaluate the pharmacokinetic parameters of orally administered metoprolol in rats."	( Enhanced oral bioavailability of metoprolol with gallic acid and ellagic acid in male Wistar rats: involvement of CYP2D6 inhibition. Athukuri, BL; Neerati, P, 2016)	0.69
"Gallic acid and ellagic acid significantly enhanced the oral bioavailability of metoprolol by inhibiting CYP2D6-mediated metabolism in the rat liver."	( Enhanced oral bioavailability of metoprolol with gallic acid and ellagic acid in male Wistar rats: involvement of CYP2D6 inhibition. Athukuri, BL; Neerati, P, 2016)	2.13
" In-silico ADME and toxicity risk assessment was done for pharmacokinetic and bioavailability compliance evaluation."	( In-silico & In-vitro Identification of Structure-Activity Relationship Pattern of Serpentine & Gallic Acid Targeting PI3Kγ as Potential Anticancer Target. Dubey, V; Kalani, K; Khan, F; Luqman, S; Sharma, P; Shukla, A; Srivastava, SK, 2017)	0.67
" Its oral bioavailability is limited by its high metabolism and rapid clearance."	( Gallic acid-PAMAM and gallic acid-phospholipid conjugates, physicochemical characterization and in vivo evaluation. Abdou, EM; Masoud, MM, 2018)	1.92
"Despite limited bioavailability and rapid degradation, dietary anthocyanins are antioxidants with cardiovascular benefits."	( Bioavailable Concentrations of Delphinidin and Its Metabolite, Gallic Acid, Induce Antioxidant Protection Associated with Increased Intracellular Glutathione in Cultured Endothelial Cells. Deakin, SJ; Duthie, GG; Goszcz, K; Megson, IL; Stewart, D, 2017)	0.69
" Results from permeability studies evidenced that SYA did not impact Imatinib's permeability across membranes while suggesting improved bioavailability through higher kinetic solubility at the biological barriers."	( Bioinspired co-crystals of Imatinib providing enhanced kinetic solubility. Dix, I; Galli, B; Gutmann, M; Harlacher, C; Holzgrabe, U; Meinel, L; Müller-Buschbaum, K; Piechon, P; Reggane, M; Saedtler, M; Wiest, J; Zottnick, SH, 2018)	0.48
" It also suggested that more attention should be paid to Mannich-type metabolites of polyphenol-formaldehyde-amino acids in research into the pharmacokinetics and bioavailability of polyphenols."	( Investigation of serum amino acids involved in gallic acid detoxification of formaldehyde by liquid chromatography/tandem mass spectrometry and neutral loss scan. Cai, N; Huang, J; Jiang, HP; Ju, XL; Wang, X, 2018)	0.74
" Pharmacokinetic analysis revealed that GA–NC displayed a characteristic sustained release profile with\ 4-fold increase in bioavailability in normal and HCC-induced rats."	( Improving Anti-Cancer Potentiality and Bioavailability of Gallic Acid by Designing Polymeric Nanocomposite Formulation Abd-Rabou, AA; Ahmed, HH; Galal, AF; Mehaya, FM; Shalby, AB, 2018)	0.73
" Therefore, approaches to improve the bioavailability and biodegradability of this poor-water soluble and non-biodegradable phenolic compound are warranted."	( New Perspectives on the Efficacy of Gallic Acid in Cosmetics & Nanocosmeceuticals. Hussain, T; Khan, BA; Mahmood, T; Menaa, F; Ray, SD; Shahzad, Y; Yousaf, AM, 2018)	0.76
"In this study, syringic acid-loaded TPGS liposome (SA-TPGS-Ls) was successfully prepared to improve oral bioavailability of syringic acid (SA)."	( Preparation and Characterization of Syringic Acid-Loaded TPGS Liposome with Enhanced Oral Bioavailability and In Vivo Antioxidant Efficiency. Adu-Frimpong, M; Li, W; Liu, Y; Sun, C; Wang, Q; Xu, X; Yu, J, 2019)	0.51
" This result implied that Leonurus japonicus houtt electuary remained longer and was absorbed slower in rats with primary dysmenorrhoea and exhibited higher bioavailability and peak concentration."	( Comparative pharmacokinetics study of leonurine and stachydrine in normal rats and rats with cold-stagnation and blood-stasis primary dysmenorrhoea after the administration of Leonurus japonicus houtt electuary. Gong, LY; Kamara, MO; Ma, HY; Meng, FH; Sun, Q; Wang, L; Wen, YQ; Zhao, N, 2019)	0.51
" The oral bioavailability of linagliptin is low (29."	( Enhanced oral bioavailability of linagliptin by the influence of gallic acid and ellagic acid in male Wistar albino rats: involvement of p-glycoprotein inhibition. Shaik, M; Vanapatla, SR, 2019)	0.75
" This study indicated the potential of phospholipids in promoting the bioavailability of EGCG3''Me and might contribute to the production of functional food with better tea catechins absorption."	( The regulation effect of EGCG3''Me phospholipid complex on gut flora of a high-fat diet-induced obesity mouse model. Cheng, L; Lin, Y; Yang, H; Zhang, X, 2019)	0.51
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."	( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019)	0.51
" Nevertheless, low solubility and bioavailability hamper the application of SA."	( Development of TPGS/F127/F68 mixed polymeric micelles: Enhanced oral bioavailability and hepatoprotection of syringic acid against carbon tetrachloride-induced hepatotoxicity. Adu-Frimpong, M; Deng, W; Li, W; Li, Y; Ma, P; Sun, C; Xu, X; Yu, J; Zhang, H; Zhu, Y, 2020)	0.56
"Cocrystallization with co-former (CCF) has proved to be a powerful approach to improve the solubility and even bioavailability of poorly water-soluble active pharmaceutical ingredients (APIs)."	( Characterizations and Assays of α-Glucosidase Inhibition Activity on Gallic Acid Cocrystals: Can the Cocrystals be Defined as a New Chemical Entity During Binding with the α-Glucosidase? He, B; Jia, Y; Li, C; Wang, J; Xue, N; Yang, C, 2020)	0.79
"The possibility of combining the health benefits of kafirin and polyphenols and improving the bioavailability of resveratrol using hollow kafirin nanoparticles via gallic acid crosslinking was investigated."	( Resveratrol-loaded hollow kafirin nanoparticles via gallic acid crosslinking: An evaluation compared with their solid and non-crosslinked counterparts. Liu, M; Pu, C; Sun, Q; Tang, W; Zhu, Y, 2020)	1
" Gallic acid (GA) is a natural polyphenol, which exhibits a broad spectrum of biological activities, but its therapeutic application was limited due to poor bioavailability and toxicity."	( Surface modified PAMAM dendrimers with gallic acid inhibit, cell proliferation, cell migration and inflammatory response to augment apoptotic cell death in human colon carcinoma cells. Kumar, A; Pathak, C; Priyadarshi, K; Sharma, A; Shirsath, K; Waghela, NB, 2021)	1.8
" However, it suffers from poor bioavailability and rapid clearance that hinders its clinical investigation."	( Impact of Reverse Micelle Loaded Lipid Nanocapsules on the Delivery of Gallic Acid into Activated Hepatic Stellate Cells: A Promising Therapeutic Approach for Hepatic Fibrosis. El-Maadawy, WH; ElMeshad, AN; Radwan, SAA; Shoukri, RA; Yousry, C, 2020)	0.79
" Solubility, dissolution rate, and oral bioavailability and hypoglycemic effect of the two cocrystals were evaluated."	( The mechanism of binding with the α-glucosidase in vitro and the evaluation on hypoglycemic effect in vivo: Cocrystals involving synergism of gallic acid and conformer. He, B; Jia, Y; Li, M; Wang, J; Xue, N; Yang, C, 2020)	0.76
" However, the therapeutic applicability of GA is hampered owing to its low bioavailability and rapid clearance."	( Zein/Phospholipid Composite Nanoparticles for Successful Delivery of Gallic Acid into aHSCs: Influence of Size, Surface Charge, and Vitamin A Coupling. El-Maadawy, WH; ElMeshad, AN; Radwan, SAA; Shoukri, RA; Yousry, C, 2020)	0.79
" Additionally, we identified supporting evidence for the nephroprotective function of gallic acid using molecular docking and bioavailability investigations."	( Identification of gallic acid as a active ingredient of Syzygium aromaticum against tacrolimus-induced damage in renal epithelial LLC-PK1 cells and rat kidney. Hong, G; Jung, K; Kang, KS; Kim, CE; Kim, DW; Lee, HL; Lee, JH; Park, M, 2021)	1.18
" The bioavailability of mango polyphenols, especially polymeric gallotannins, is largely dependent on the intestinal microbiota, where the generation of absorbable metabolites depends on microbial enzymes."	( Mango ( Arbizu, S; Castellon-Chicas, MJ; Drury, NL; Kim, H; Mertens-Talcott, SU; Smith, S; Talcott, ST, 2021)	0.62
" Plant-derived-natural products have poor bioavailability which restricts their anti-tumor activity."	( Gallic acid for cancer therapy: Molecular mechanisms and boosting efficacy by nanoscopical delivery. Ahn, KS; Ang, HL; Ashrafizadeh, M; Hashemi, F; Hushmandi, K; Khan, H; Kumar, AP; Makvandi, P; Mirzaei, S; Nabavi, N; Samarghandian, S; Sethi, G; Varma, RS; Zabolian, A; Zarrabi, A, 2021)	2.06
" In addition nanotechnology-mediated approaches are also discussed to enhance bioavailability and therapeutic efficacy."	( Gallic Acid: A Dietary Polyphenol that Exhibits Anti-neoplastic Activities by Modulating Multiple Oncogenic Targets. Aggarwal, D; Garg, VK; Kaur, G; Khan, MA; Mistry, H; Mittal, S; Sak, K; Tuli, HS; Yerer, MB, 2022)	2.16
" In normal and DMH-induced rats, a pharmacokinetic study demonstrated that polyherbal nanoparticles had a typical sustained release profile with a fourfold increase in bioavailability when compared to polyherbal extract."	( Improving gallic acid and quercetin bioavailability by polymeric nanoparticle formulation. Killedar, S; Patil, P, 2021)	1.02
"The objective of this study was to assess how in vitro gastrointestinal digestion influenced the bioaccessibility and potential bioavailability of phenolic compounds and methylxanthines in thecocoa shell (CS) in the form of flour (CSF) and aqueous extract (CSE)."	( Gastrointestinal fate of phenolic compounds and amino derivatives from the cocoa shell: An in vitro and in silico approach. Aguilera, Y; Benítez, V; Braojos, C; Cañas, S; Dueñas, M; Ferreras-Charro, R; Martín-Cabrejas, MA; Rebollo-Hernanz, M, 2022)	0.72
" The phenethyl ester of gallic acid (PEGA) was synthesized with the aim of increasing the bioavailability of gallic acid, and thus its pharmacological potential."	( Phenethyl Ester of Gallic Acid Ameliorates Experimental Autoimmune Encephalomyelitis. Antoniou, T; Dimitrijević, M; Djedovic, N; Gkalpinos, VK; Jevtić, B; Lazarević, M; Miljković, Đ; Momčilović, M; Stanisavljević, S; Stegnjaić, G; Tsiailanis, AD; Tzakos, AG, 2022)	1.36
" A complex synthesized from GA and soybean lecithin (SL-GAC), significantly improved bioavailability of GA and pharmacological activities."	( Amelioration effects of the soybean lecithin-gallic acid complex on iron-overload-induced oxidative stress and liver damage in C57BL/6J mice. Cui, W; Dai, W; Fang, F; Gao, Y; Wu, C; Yan, F; Zhang, W, 2023)	1.17

Excerpt	Relevance	Reference
" The dose-response curve for this suppression was very similar to that for stimulation of inositol monophosphate (IP1) formation and for stimulation of the initial rise of [Ca2+]i elicited by carbachol."	( Suppressive effect of carbachol on forskolin-stimulated neurite outgrowth in human neuroblastoma NB-OK1 cells. Nakagawa-Yagi, Y; Nakamura, H; Saito, Y; Takada, Y, 1992)	0.28
" From cumulative dose-response curves, pD2 values of various calcium antagonists for the negative inotropic activity were determined in diabetic and control hearts."	( Effects of various calcium antagonists in isolated perfused hearts from diabetic and age-matched control rats. Heijnis, JB; Mathy, MJ; van Zwieten, PA, 1991)	0.28
" In spite of the high dosage as well as the large interindividual variability in the urinary recovery and the serum concentrations potential "toxic" serum levels of 100 micrograms/l were never reached."	( [Effect of meals on resorption of bismuth from an oral bismuth gallate/bismuth nitrate preparation]. Klotz, U; Leonhardt, H, 1991)	0.28
" In addition, the similarity of the dose-response curves for the bradykinin-mediated increase in Ca2+, PGE2, and cAMP (half-maximal stimulation of 12, 11, and 13 nM, respectively) and the ability of the B2-antagonist (B4307) to block each of these effects of bradykinin suggest that all three effects are mediated by the same bradykinin (B2) receptor."	( Effects of kinins on cultured arterial smooth muscle. Breckon, R; Dixon, BS; Fortune, J; Linas, SL; Marzec-Calvert, R; Stewart, JM; Vavrek, RJ, 1990)	0.28
" In the presence of TMB-8 the dose-response curve for carbachol-induced amylase release shifts to the right, suggesting competitive antagonism at the muscarinic receptor."	( Stimulatory and inhibitory effects of TMB-8 on pancreatic enzyme secretion. De Pont, JJ; Van Nooij, IG; Willems, PH, 1986)	0.27
" Furthermore, enhancement of the respiratory burst and calcium transients occurred in a parallel dose-response range for rIFN-gamma."	( Relation of cytosolic calcium to the microbicidal activation of blood monocytes by recombinant gamma interferon. Kemmerich, B; Pennington, JE; Small, GJ, 1986)	0.27
" Intravenously administered PGE2 at a five times higher dosage failed to significantly alter net water and electrolyte fluxes."	( Central nervous system influence of prostaglandin E2 on jejunal water and electrolyte transport in conscious dogs. Bueno, L; Primi, MP, 1986)	0.27
" The dose-response curve of the fluorescence change and that of the superoxide release of th cells were very similar."	( Release of the membrane-calcium and its relation to the superoxide formation by polymorphonuclear leukocytes. Matsumoto, T; Minakami, S; Nabi, ZF; Takeshige, K, 1982)	0.26
" A dose-response relationship resulted when explants were challenged with methacholine in nutrient medium containing varied calcium concentrations (0."	( The calcium dependency of mucus glycoconjugate secretion by canine tracheal explants. Barbieri, EJ; Bobyock, E; Chernick, WS; McMichael, RF, 1984)	0.27
"An ion-pair column chromatographic/UV spectrophotometric method for assaying trimethobenzamide hydrochloride in capsules and injections is presented, as well as a method for the detection of 3,4,5- trimethoxybenzoic acid in trimethobenzamide hydrochloride bulk drug and dosage forms."	( Quantitative analysis of trimethobenzamide hydrochloride by ion-pair column chromatography and semiquantitative analysis of 3,4,5-trimethoxybenzoic acid by thin-layer chromatography. Naviasky, H, 1984)	0.27
" Nifedipine (100 micrograms/kg, 300 micrograms/kg, and 1000 micrograms/kg) inhibited in a dose-dependent manner the pressor responses to the alpha 1- and alpha 2-adrenoceptor agonists, the dose-response curves to the alpha 2-adrenoceptor agonists being shifted further to the right."	( A comparison of the effects of TMB-8 and nifedipine on pressor responses to alpha 1- and alpha 2-adrenoceptor agonists in pithed rats. Aleixandre, MA; Pintado, A; Puerro, M, 1995)	0.29
" Rats that were not dosed with NMBA had no tumors."	( Effects of theaflavins on N-nitrosomethylbenzylamine-induced esophageal tumorigenesis. Balentine, DA; Boone, CW; Harbowy, ME; Kelloff, GJ; Kresty, LA; Morse, MA; Steele, VE; Stoner, GD, 1997)	0.3
" The antioxidant capacity of Gala apples and seven phenolic standards, determined by both ABTS()(-) and DPPH() scavenging assays, showed a dose-response of the first-order."	( Vitamin C equivalent antioxidant capacity (VCEAC) of phenolic phytochemicals. Kim, DO; Lee, CY; Lee, HJ; Lee, KW, 2002)	0.31
" Rightward shift of the dose-response curves due to coinfusion of inhibitors served to assess contribution of different pathways: trimethoxybenzoate (TMB-8) against Ca2+ mobilization, nifedipine against Ca2+ influx, staurosporine and Ro-318220 against PKC, and Y-27632 and HA-1077 against ROK."	( Variations in cell signaling pathways for different vasoconstrictor agonists in renal circulation of the rat. Bauer, J; Parekh, N, 2003)	0.32
" They shifted dose-response curves of Ang II, norepinephrine, and AVP to sevenfold and higher values."	( Variations in cell signaling pathways for different vasoconstrictor agonists in renal circulation of the rat. Bauer, J; Parekh, N, 2003)	0.32
" The 500 mg/kg GSH ester reduced hearing loss and OHC loss, but protection decreased as dosage increased, suggesting possible toxicity."	( Glutathione ester but not glutathione protects against cisplatin-induced ototoxicity in a rat model. Campbell, KC; Hughes, LF; Larsen, DL; Meech, RP; Rybak, LP, 2003)	0.32
" The serum concentration of intact CA in the portal vein peaked 10 min after dosing (C(max) was 165."	( Intestinal absorption of p-coumaric and gallic acids in rats after oral administration. Hitomi, Y; Konishi, Y; Yoshioka, E, 2004)	0.59
" It is natural and potent enough for manageable dosing regimens."	( Black raspberry extract and fractions contain angiogenesis inhibitors. Anthony, CT; Greenway, FL; Liu, D; Liu, Z; Schwimer, J; Woltering, EA, 2005)	0.33
" Rats were orally administrated gentisic acid (GEA), gallic acid (GA), ferulic acid (FA), and p-coumaric acid (p-CA) at a dosage of 100 mg/kg body weight for 14 consecutive days."	( Induction of hepatic antioxidant enzymes by phenolic acids in rats is accompanied by increased levels of multidrug resistance-associated protein 3 mRNA expression. Yeh, CT; Yen, GC, 2006)	0.58
" According to the results, gentisic acid, gallic acid and p-coumaric acid in a dosage of 100 mg/kg of body weight for 14 consecutive days significantly increased P-form PST (PST-P) activity as compared with that of the control rats (P<."	( Modulation of hepatic phase II phenol sulfotransferase and antioxidant status by phenolic acids in rats. Yeh, CT; Yen, GC, 2006)	0.6
" The results demonstrated that the extract at dosage of 40-225 mg/100 g significantly increased the activity of SOD (superoxide dismutase) and reduced the lipid peroxidation in both blood and liver of rat."	( In vitro and vivo antioxidant activities of daylily flowers and the involvement of phenolic compounds. Mao, L; Que, F; Zheng, X, 2007)	0.34
" Gallic acid, ferulic acid and p-coumaric acid at a dosage of 100 mg kg(-1) body weight significantly increased the activities of cardiac superoxide dismutase, glutathione peroxidase (GPx) and catalase (CAT) as compared with control rats (P<."	( Inducing gene expression of cardiac antioxidant enzymes by dietary phenolic acids in rats. Ching, LC; Yeh, CT; Yen, GC, 2009)	1.26
" To investigate whether similar effects are present in the hippocampus, AMPA dose-response and calcium movement blockade were performed."	( Nimodipine inhibits TMB-8 potentiation of AMPA-induced hippocampal neurodegeneration. Bernal, F; Mahy, N; Petegnief, V; Pugliese, M; Rodríguez, MJ; Ursu, G, 2009)	0.35
" niveum were stimulated at lower concentrations of syringic acid, though inhibited by higher dosage compared with control."	( In vitro physiological responses of Fusarium oxysporum f. sp. niveum to exogenously applied syringic acid. Cao, Y; Chen, AQ; Chen, G; Huang, QW; Liu, YX; Luo, J; Mao, ZS; Shen, QR; Tang, Z; Wu, HS, )	0.13
" This study suggests that brain deposition of GA, C, and EC is affected by repeated dosing of GSPE."	( Bioavailability of gallic acid and catechins from grape seed polyphenol extract is improved by repeated dosing in rats: implications for treatment in Alzheimer's disease. Cooper, B; Ferruzzi, MG; Ho, L; Janle, EM; Lobo, JK; Pasinetti, GM; Simon, JE; Weaver, C; Welch, C; Wu, QL, 2009)	0.68
" Because diabetes is associated with increased oxidative stress, we hypothesized that a labeled recombinant PON1 (rePON1) would detect differences in HDL capacity to bind PON1 under specific experimental conditions, such as oxidation, addition of polyphenols, or in vivo dosing of diabetic patients with polyphenols."	( Pomegranate juice polyphenols increase recombinant paraoxonase-1 binding to high-density lipoprotein: studies in vitro and in diabetic patients. Aviram, M; Fuhrman, B; Volkova, N, 2010)	0.36
"The bioavailability values observed are in agreement with previous reports, although the dosage of polyphenols ingested in this study is remarkably lower."	( Bioavailability of catechins from ready-to-drink tea. Brighenti, F; Calani, L; Cordero, C; Del Rio, D; Jechiu, L; Scazzina, F, 2010)	0.36
" From this active fraction, seven compounds have been isolated and four compounds (pinosylvin, galangin, quercetin and methyl gallate) have been examined for their dose-response effect on the viability of A549 cells and on TNF-α inhibitory activity."	( Bioactivity guided isolation of anticancer constituents from leaves of Alnus sieboldiana (Betulaceae). Asakawa, Y; Kuzuhara, T; Ludwiczuk, A; Saha, A, 2011)	0.37
" To understand the GA effects on the endogenous metabolism of mammals, we systematically analyzed the metabonomic responses of rat plasma, liver, urine, and feces to a single GA dosage of 120 and 600 mg/kg, which were below the no-obvious-adverse-effect-level of 1 g/kg for rats."	( Gallic acid intake induces alterations to systems metabolism in rats. Shi, X; Tang, H; Wang, Y; Xiao, C, 2013)	1.83
" Moreover, the high dosage used indicates low potency of leonurine."	( 3,5-Dimethoxy-4-(3-(2-carbonyl-ethyldisulfanyl)-propionyl)-benzoic acid 4-guanidino-butyl ester: a novel twin drug that prevents primary cardiac myocytes from hypoxia-induced apoptosis. Gu, X; Guo, W; Liu, C; Maerz, S; Zhu, Y, 2013)	0.39
"A dehydrated vegetables mixture loaded in four pharmaceutical dosage forms as powder, effervescent granulate, sugar granulate and gumdrops were investigated for their antioxidant capacity using 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) radical scavenging capacity assay, oxygen radical absorbance capacity assay and ferric reducing antioxidant potential assay."	( Antioxidant activity evaluation of new dosage forms as vehicles for dehydrated vegetables. Clares-Naveros, B; Fernández-Arroyo, S; Fernández-Campos, F; García-Salas, P; Romero-de Soto, MD; Segura-Carretero, A, 2013)	0.39
" With extraction rate of salidroside, tyrosol, crenulatin and gallic acid as indexes, orthogonal test was used to evaluate effect of 4 factors on extracting technology, including concentration of solvent, the dosage of solvent, duration of extraction, and frequency of extraction."	( [Optimization of extraction technology for salidroside, tyrosol, crenulatin and gallic acid in Rhodiolae Crenulatae Radix et Rhizoma with orthogonal test]. Huang, WZ; Luo, X; Wang, XJ; Wang, ZZ; Xiao, W; Zhao, YW, 2015)	0.88
" PG low aqueous solubility represents a major drawback to its incorporation in topical dosage forms."	( Pentyl Gallate Nanoemulsions as Potential Topical Treatment of Herpes Labialis. Colombo, M; Dall Agnol, D; De Araújo Lopes, SC; Kelmann, RG; Koester, LS; Nunes, RJ; Oliveira Simões, CM; Pistore, M; Rigotto, C; Roman, SS; Silva, IT; Teixeira, HF, 2016)	0.43
" Single dosing of NADPH or omitting toxic components from the MAS preparation did also not reduce embryotoxicity."	( Antioxidants reduce reactive oxygen species but not embryotoxicity in the metabolic Danio rerio test (mDarT). Bars, C; Knapen, D; Pype, C; Saad, MA; Van Cruchten, SJ; Van Ginneken, CJ; Verbueken, E, 2017)	0.46
" These animal data need to be confirmed in a clinical setting to determine whether linagliptin dosing should be adjusted when given concomitantly with these phytochemicals or gallic acid/ellagic acid-containing dietary supplements."	( Enhanced oral bioavailability of linagliptin by the influence of gallic acid and ellagic acid in male Wistar albino rats: involvement of p-glycoprotein inhibition. Shaik, M; Vanapatla, SR, 2019)	0.94
" 90% lethality of IJs at concentrations higher than 1200 ppm and the remaining live IJs did not develop further, and they also totally inhibited strongyle L3 exsheathment in a dose-response fashion."	( Can an entomopathogenic nematode serve, as proxy for strongyles, in assessing the anthelmintic effects of phenolic compounds? Awwad, S; Azaizeh, H; Glazer, I; Haj-Zaroubi, M; Landau, SY; Markovics, A; Muklada, H; Salame, L; Santhi, VS, 2020)	0.56
" According to pharmacokinetic studies, the absorption and elimination of GA after oral administration are fast, while the structural optimization or dosage form adjustment of GA is beneficial to increase its bioavailability."	( Gallic acid: Pharmacological activities and molecular mechanisms involved in inflammation-related diseases. Ai, X; Bai, J; Chen, X; Hou, Y; Meng, X; Tang, C; Wang, X; Zhang, Y, 2021)	2.06
" The dose-response analysis of MG (0."	( Protective effect of methyl gallate on murine antigen-induced arthritis by inhibiting inflammatory process and bone erosion. Alabarse, PVG; Amendoeira, FC; Correa, LB; Ferraris, FK; Fukada, SY; Garcia, EB; Henriques, MG; Pádua, TA; Rosas, EC; Saraiva, EM, 2022)	0.72
" Our data showed that GA administration by oral gavage at a daily dosage of 20 mg/kg body weight did not significantly ameliorate WTD-induced hyperlipidemia, hepatosteatosis, adipogenesis, or insulin resistance; furthermore, GA administration did not significantly ameliorate WTD-induced atherosclerosis."	( Low-Dose Gallic Acid Administration Does Not Improve Diet-Induced Metabolic Disorders and Atherosclerosis in Apoe Knockout Mice. An, X; Bai, J; Liao, J; Lin, QY; Liu, S; Wang, Y; Xie, Y, 2022)	1.14
" Developing allelochemical-based algicides has previously faced difficulties, including dosage requirements and chemical instability."	( Necrosis of Microcystis aeruginosa causing tannin derivatives in Rhus chinensis stem. Eom, SH; Lim, YJ, 2023)	0.91
" After 56 days of oral FEX treatment, the total ACF number in the low FEX dosage (DL) group was significantly lower compared to the D group (p < 0."	( Jaboticaba (Myrciaria cauliflora) Fruit Extract Suppressed Aberrant Crypt Formation in 1,2-Dimetylhydrazine-Induced Rats. Ardanareswari, K; Chung, YC; Liao, JW; Lowisia, W; Soedarini, B, 2023)	0.91
"A simple, rapid, precise, sensitive, and reproducible reverse-phase high-performance liquid chromatography (RP-HPLC) method has been developed for the quantitative analysis of gallic acid in the pharmaceutical dosage form."	( Method Development and Validation of Gallic Acid in Liquid Dosage Form by Using RP-HPLC Method. Maheshwari, PU; Munemma, R; Roja, A; Swathi, K, 2023)	1.38

Role	Description
astringent	A compound that causes the contraction of body tissues, typically used to reduce bleeding from minor abrasions.
cyclooxygenase 2 inhibitor	A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
plant metabolite	Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
antioxidant	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
antineoplastic agent	A substance that inhibits or prevents the proliferation of neoplasms.
human xenobiotic metabolite	Any human metabolite produced by metabolism of a xenobiotic compound in humans.
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor	A lipoxygenase inhibitor that interferes with the action of arachidonate 15-lipoxygenase (EC 1.13.11.33).
apoptosis inducer	Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
geroprotector	Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Class	Description
trihydroxybenzoic acid
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathway	Proteins	Compounds
Flavan-3-ol metabolic pathway	0	70

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASE	Homo sapiens (human)	Potency	16.1269	0.0032	45.4673	12,589.2998	AID2517
Chain A, TYROSYL-DNA PHOSPHODIESTERASE	Homo sapiens (human)	Potency	11.7116	0.0040	23.8416	100.0000	AID485290; AID489007
Chain A, Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	8.8325	0.1409	11.1940	39.8107	AID2451; AID2787
Chain A, HADH2 protein	Homo sapiens (human)	Potency	10.0014	0.0251	20.2376	39.8107	AID886; AID893
Chain B, HADH2 protein	Homo sapiens (human)	Potency	10.0014	0.0251	20.2376	39.8107	AID886; AID893
Chain A, 2-oxoglutarate Oxygenase	Homo sapiens (human)	Potency	0.3548	0.1778	14.3909	39.8107	AID2147
Luciferase	Photinus pyralis (common eastern firefly)	Potency	51.2881	0.0072	15.7588	89.3584	AID1224835
interleukin 8	Homo sapiens (human)	Potency	47.3079	0.0473	49.4806	74.9780	AID651758
acetylcholinesterase	Homo sapiens (human)	Potency	80.4210	0.0025	41.7960	15,848.9004	AID1347398
phosphopantetheinyl transferase	Bacillus subtilis	Potency	8.9125	0.1413	37.9142	100.0000	AID1490
RAR-related orphan receptor gamma	Mus musculus (house mouse)	Potency	26.6032	0.0060	38.0041	19,952.5996	AID1159521
GLS protein	Homo sapiens (human)	Potency	10.0000	0.3548	7.9355	39.8107	AID624170
TDP1 protein	Homo sapiens (human)	Potency	14.4911	0.0008	11.3822	44.6684	AID686978; AID686979
GLI family zinc finger 3	Homo sapiens (human)	Potency	24.4118	0.0007	14.5928	83.7951	AID1259369; AID1259392
Microtubule-associated protein tau	Homo sapiens (human)	Potency	1.6271	0.1800	13.5574	39.8107	AID1460; AID1468
AR protein	Homo sapiens (human)	Potency	6.0070	0.0002	21.2231	8,912.5098	AID743036
aldehyde dehydrogenase 1 family, member A1	Homo sapiens (human)	Potency	5.4539	0.0112	12.4002	100.0000	AID1030
hypothetical protein, conserved	Trypanosoma brucei	Potency	12.5893	0.2239	11.2451	35.4813	AID624173
cytochrome P450 family 3 subfamily A polypeptide 4	Homo sapiens (human)	Potency	1.7377	0.0123	7.9835	43.2770	AID1645841
glucocorticoid receptor [Homo sapiens]	Homo sapiens (human)	Potency	9.8875	0.0002	14.3764	60.0339	AID588533; AID720691; AID720692
retinoic acid nuclear receptor alpha variant 1	Homo sapiens (human)	Potency	59.9623	0.0030	41.6115	22,387.1992	AID1159552; AID1159553; AID1159555
estrogen-related nuclear receptor alpha	Homo sapiens (human)	Potency	40.5271	0.0015	30.6073	15,848.9004	AID1224841; AID1224848; AID1224849; AID1259401; AID1259403
farnesoid X nuclear receptor	Homo sapiens (human)	Potency	62.2336	0.3758	27.4851	61.6524	AID743220
estrogen nuclear receptor alpha	Homo sapiens (human)	Potency	38.8472	0.0002	29.3054	16,493.5996	AID1259244; AID1259248; AID588514; AID743075
67.9K protein	Vaccinia virus	Potency	19.7020	0.0001	8.4406	100.0000	AID720579; AID720580
euchromatic histone-lysine N-methyltransferase 2	Homo sapiens (human)	Potency	1.9953	0.0355	20.9770	89.1251	AID504332
cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_a	Homo sapiens (human)	Potency	69.2179	0.0017	23.8393	78.1014	AID743083
v-jun sarcoma virus 17 oncogene homolog (avian)	Homo sapiens (human)	Potency	58.8496	0.0578	21.1097	61.2679	AID1159526; AID1159528
Histone H2A.x	Cricetulus griseus (Chinese hamster)	Potency	31.8759	0.0391	47.5451	146.8240	AID1224845; AID1224896
cellular tumor antigen p53 isoform a	Homo sapiens (human)	Potency	11.2947	0.3162	12.4435	31.6228	AID902; AID924
15-hydroxyprostaglandin dehydrogenase [NAD(+)] isoform 1	Homo sapiens (human)	Potency	7.0795	0.0018	15.6638	39.8107	AID894
vitamin D3 receptor isoform VDRA	Homo sapiens (human)	Potency	50.1187	0.3548	28.0659	89.1251	AID504847
fructose-bisphosphate aldolase A	Oryctolagus cuniculus (rabbit)	Potency	19.9526	0.8913	16.5762	39.8107	AID2794
thyroid hormone receptor beta isoform 2	Rattus norvegicus (Norway rat)	Potency	49.3276	0.0003	23.4451	159.6830	AID743065; AID743067
heat shock protein beta-1	Homo sapiens (human)	Potency	55.4657	0.0420	27.3789	61.6448	AID743210
glyceraldehyde-3-phosphate dehydrogenase isoform 1	Homo sapiens (human)	Potency	25.1189	1.1220	11.1877	39.8107	AID2795
mitogen-activated protein kinase 1	Homo sapiens (human)	Potency	23.7530	0.0398	16.7842	39.8107	AID1454; AID995
nuclear factor erythroid 2-related factor 2 isoform 1	Homo sapiens (human)	Potency	5.5630	0.0006	27.2152	1,122.0200	AID651741; AID743202; AID743219
nuclear receptor ROR-gamma isoform 1	Mus musculus (house mouse)	Potency	13.8914	0.0079	8.2332	1,122.0200	AID2546; AID2551
DNA polymerase kappa isoform 1	Homo sapiens (human)	Potency	10.0000	0.0316	22.3146	100.0000	AID588579
survival motor neuron protein isoform d	Homo sapiens (human)	Potency	15.8489	0.1259	12.2344	35.4813	AID1458
histone acetyltransferase KAT2A isoform 1	Homo sapiens (human)	Potency	39.8107	0.2512	15.8432	39.8107	AID504327
lethal factor (plasmid)	Bacillus anthracis str. A2012	Potency	15.8489	0.0200	10.7869	31.6228	AID912
lamin isoform A-delta10	Homo sapiens (human)	Potency	0.2818	0.8913	12.0676	28.1838	AID1487
Voltage-dependent calcium channel gamma-2 subunit	Mus musculus (house mouse)	Potency	49.0025	0.0015	57.7890	15,848.9004	AID1259244
Cellular tumor antigen p53	Homo sapiens (human)	Potency	5.4982	0.0023	19.5956	74.0614	AID651631
Integrin beta-3	Homo sapiens (human)	Potency	12.5893	0.3162	11.4157	31.6228	AID924
Integrin alpha-IIb	Homo sapiens (human)	Potency	12.5893	0.3162	11.4157	31.6228	AID924
Glutamate receptor 2	Rattus norvegicus (Norway rat)	Potency	49.0025	0.0015	51.7393	15,848.9004	AID1259244
ATP-dependent phosphofructokinase	Trypanosoma brucei brucei TREU927	Potency	31.6228	0.0601	10.7453	37.9330	AID492961
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Carbonic anhydrase 12	Homo sapiens (human)	Ki	7.7800	0.0002	1.1043	9.9000	AID462279
Pancreatic triacylglycerol lipase	Sus scrofa (pig)	IC50 (µMol)	1,000.0000	0.0040	1.1024	6.5000	AID691434
Urokinase-type plasminogen activator	Homo sapiens (human)	IC50 (µMol)	6.6000	0.0370	3.3859	10.0000	AID1799783
Tissue-type plasminogen activator	Homo sapiens (human)	IC50 (µMol)	6.6000	0.0340	2.5425	6.6000	AID1799783
Carbonic anhydrase 1	Homo sapiens (human)	Ki	604.4000	0.0000	1.3726	10.0000	AID1799599; AID462270
Carbonic anhydrase 2	Homo sapiens (human)	Ki	604.0833	0.0000	0.7236	9.9200	AID1799599; AID462271
Plasminogen activator inhibitor 1	Homo sapiens (human)	IC50 (µMol)	6.6000	0.0910	4.8928	10.0000	AID1799783
Urokinase-type plasminogen activator	Mus musculus (house mouse)	IC50 (µMol)	6.6000	0.0910	2.9202	6.6000	AID1799783
Carbonic anhydrase 3	Homo sapiens (human)	Ki	7.4900	0.0002	2.0102	10.0000	AID462272
72 kDa type IV collagenase	Homo sapiens (human)	IC50 (µMol)	65.0086	0.0000	1.2848	10.0000	AID1799773
Matrilysin	Homo sapiens (human)	IC50 (µMol)	65.0086	0.0014	2.0859	10.0000	AID1799773
Angiotensin-converting enzyme	Homo sapiens (human)	IC50 (µMol)	7,700.0000	0.0001	0.5336	10.0000	AID338980
P-selectin	Homo sapiens (human)	IC50 (µMol)	19.1000	5.0000	5.0000	5.0000	AID280291
E-selectin	Homo sapiens (human)	IC50 (µMol)	500.0000	0.0200	2.2133	6.6000	AID280289
Prolyl 4-hydroxylase subunit alpha-1	Gallus gallus (chicken)	Ki	30.0000	5.0000	7.6667	9.0000	AID1799825
Carbonic anhydrase 4	Homo sapiens (human)	Ki	9.8000	0.0002	1.9720	9.9200	AID462273
Carbonic anhydrase 6	Homo sapiens (human)	Ki	6.1300	0.0001	1.4710	9.9200	AID462276
Adenosine receptor A1	Rattus norvegicus (Norway rat)	Ki	8.2600	0.0001	1.2092	9.9700	AID462275; AID462279; AID462281
Dipeptidyl peptidase 4	Homo sapiens (human)	IC50 (µMol)	4.6500	0.0001	0.4444	10.0000	AID1395903
Proteasome subunit beta type-5	Homo sapiens (human)	IC50 (µMol)	7,100.0000	0.0005	0.9394	10.0000	AID1633145
Nitric oxide synthase, inducible	Mus musculus (house mouse)	IC50 (µMol)	50.0000	0.0010	3.3911	9.6000	AID344829
Adenosine receptor A2a	Rattus norvegicus (Norway rat)	Ki	6.5500	0.0002	1.4940	10.0000	AID462277; AID462281
Carbonic anhydrase 5A, mitochondrial	Homo sapiens (human)	Ki	4.0800	0.0000	1.2725	9.9000	AID462274
Alpha-synuclein	Homo sapiens (human)	IC50 (µMol)	4.4300	0.1900	3.8204	9.8000	AID1664684
Carbonic anhydrase 7	Homo sapiens (human)	Ki	6.0700	0.0002	1.3737	9.9000	AID462277
4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT6	Homo sapiens (human)	IC50 (µMol)	65.0086	0.0600	3.8956	8.3000	AID1799773
Squalene monooxygenase	Rattus norvegicus (Norway rat)	IC50 (µMol)	73.0000	0.0610	2.3446	10.0000	AID357307
Autoinducer 2-binding periplasmic protein LuxP	Vibrio harveyi	IC50 (µMol)	50.0000	2.0000	3.0000	4.0000	AID314588
Anthrax toxin receptor 2	Homo sapiens (human)	IC50 (µMol)	300.0000	0.3000	0.4535	0.6070	AID725981
Disintegrin and metalloproteinase domain-containing protein 17	Homo sapiens (human)	IC50 (µMol)	200.0000	0.0002	1.0140	10.0000	AID1799774
Polypeptide N-acetylgalactosaminyltransferase 2	Homo sapiens (human)	IC50 (µMol)	1.3700	0.5100	1.6437	3.1200	AID1588066
Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)	IC50 (µMol)	65.0086	0.0600	3.8956	8.3000	AID1799773
CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)	IC50 (µMol)	65.0086	0.0600	3.8956	8.3000	AID1799773
Carbonic anhydrase 9	Homo sapiens (human)	Ki	6.9900	0.0001	0.7874	9.9000	AID462278
Carbonic anhydrase	Dicentrarchus labrax (European seabass)	Ki	4.1300	2.1300	5.5333	9.4100	AID607497
Reverse transcriptase/RNaseH	Human immunodeficiency virus 1	IC50 (µMol)	100.0000	0.0001	1.0768	10.0000	AID83435
Carbonic anhydrase 13	Mus musculus (house mouse)	Ki	9.8600	0.0002	1.3974	9.9000	AID462280
Carbonic anhydrase 14	Homo sapiens (human)	Ki	7.0300	0.0002	1.5099	9.9000	AID462281
Carbonic anhydrase 5B, mitochondrial	Homo sapiens (human)	Ki	9.9700	0.0000	1.3412	9.9700	AID462275
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Polypeptide N-acetylgalactosaminyltransferase 2	Homo sapiens (human)	Kd	0.9240	0.2940	0.5297	0.9240	AID1588067
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Lactoperoxidase	Bos taurus (cattle)	Km	176.7800	0.3000	1.5778	8.4100	AID1490876
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
estrous cycle	Carbonic anhydrase 12	Homo sapiens (human)
chloride ion homeostasis	Carbonic anhydrase 12	Homo sapiens (human)
one-carbon metabolic process	Carbonic anhydrase 12	Homo sapiens (human)
positive regulation of cell migration	Urokinase-type plasminogen activator	Homo sapiens (human)
response to hypoxia	Urokinase-type plasminogen activator	Homo sapiens (human)
proteolysis	Urokinase-type plasminogen activator	Homo sapiens (human)
chemotaxis	Urokinase-type plasminogen activator	Homo sapiens (human)
signal transduction	Urokinase-type plasminogen activator	Homo sapiens (human)
blood coagulation	Urokinase-type plasminogen activator	Homo sapiens (human)
regulation of signaling receptor activity	Urokinase-type plasminogen activator	Homo sapiens (human)
regulation of plasminogen activation	Urokinase-type plasminogen activator	Homo sapiens (human)
negative regulation of plasminogen activation	Urokinase-type plasminogen activator	Homo sapiens (human)
smooth muscle cell migration	Urokinase-type plasminogen activator	Homo sapiens (human)
regulation of smooth muscle cell migration	Urokinase-type plasminogen activator	Homo sapiens (human)
regulation of cell adhesion	Urokinase-type plasminogen activator	Homo sapiens (human)
plasminogen activation	Urokinase-type plasminogen activator	Homo sapiens (human)
regulation of cell adhesion mediated by integrin	Urokinase-type plasminogen activator	Homo sapiens (human)
urokinase plasminogen activator signaling pathway	Urokinase-type plasminogen activator	Homo sapiens (human)
regulation of cell population proliferation	Urokinase-type plasminogen activator	Homo sapiens (human)
fibrinolysis	Urokinase-type plasminogen activator	Homo sapiens (human)
regulation of fibrinolysis	Urokinase-type plasminogen activator	Homo sapiens (human)
negative regulation of fibrinolysis	Urokinase-type plasminogen activator	Homo sapiens (human)
regulation of wound healing	Urokinase-type plasminogen activator	Homo sapiens (human)
regulation of smooth muscle cell-matrix adhesion	Urokinase-type plasminogen activator	Homo sapiens (human)
response to hypoxia	Tissue-type plasminogen activator	Homo sapiens (human)
proteolysis	Tissue-type plasminogen activator	Homo sapiens (human)
blood coagulation	Tissue-type plasminogen activator	Homo sapiens (human)
negative regulation of plasminogen activation	Tissue-type plasminogen activator	Homo sapiens (human)
plasminogen activation	Tissue-type plasminogen activator	Homo sapiens (human)
protein modification process	Tissue-type plasminogen activator	Homo sapiens (human)
fibrinolysis	Tissue-type plasminogen activator	Homo sapiens (human)
negative regulation of proteolysis	Tissue-type plasminogen activator	Homo sapiens (human)
negative regulation of fibrinolysis	Tissue-type plasminogen activator	Homo sapiens (human)
prevention of polyspermy	Tissue-type plasminogen activator	Homo sapiens (human)
trans-synaptic signaling by BDNF, modulating synaptic transmission	Tissue-type plasminogen activator	Homo sapiens (human)
platelet-derived growth factor receptor signaling pathway	Tissue-type plasminogen activator	Homo sapiens (human)
smooth muscle cell migration	Tissue-type plasminogen activator	Homo sapiens (human)
one-carbon metabolic process	Carbonic anhydrase 1	Homo sapiens (human)
morphogenesis of an epithelium	Carbonic anhydrase 2	Homo sapiens (human)
positive regulation of synaptic transmission, GABAergic	Carbonic anhydrase 2	Homo sapiens (human)
positive regulation of cellular pH reduction	Carbonic anhydrase 2	Homo sapiens (human)
angiotensin-activated signaling pathway	Carbonic anhydrase 2	Homo sapiens (human)
regulation of monoatomic anion transport	Carbonic anhydrase 2	Homo sapiens (human)
secretion	Carbonic anhydrase 2	Homo sapiens (human)
regulation of intracellular pH	Carbonic anhydrase 2	Homo sapiens (human)
neuron cellular homeostasis	Carbonic anhydrase 2	Homo sapiens (human)
positive regulation of dipeptide transmembrane transport	Carbonic anhydrase 2	Homo sapiens (human)
regulation of chloride transport	Carbonic anhydrase 2	Homo sapiens (human)
carbon dioxide transport	Carbonic anhydrase 2	Homo sapiens (human)
one-carbon metabolic process	Carbonic anhydrase 2	Homo sapiens (human)
negative regulation of cell population proliferation	Cellular tumor antigen p53	Homo sapiens (human)
regulation of cell cycle	Cellular tumor antigen p53	Homo sapiens (human)
regulation of cell cycle G2/M phase transition	Cellular tumor antigen p53	Homo sapiens (human)
DNA damage response	Cellular tumor antigen p53	Homo sapiens (human)
ER overload response	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to glucose starvation	Cellular tumor antigen p53	Homo sapiens (human)
intrinsic apoptotic signaling pathway in response to DNA damage by p53 class mediator	Cellular tumor antigen p53	Homo sapiens (human)
regulation of apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of transcription by RNA polymerase II	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of miRNA transcription	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of transcription by RNA polymerase II	Cellular tumor antigen p53	Homo sapiens (human)
mitophagy	Cellular tumor antigen p53	Homo sapiens (human)
in utero embryonic development	Cellular tumor antigen p53	Homo sapiens (human)
somitogenesis	Cellular tumor antigen p53	Homo sapiens (human)
release of cytochrome c from mitochondria	Cellular tumor antigen p53	Homo sapiens (human)
hematopoietic progenitor cell differentiation	Cellular tumor antigen p53	Homo sapiens (human)
T cell proliferation involved in immune response	Cellular tumor antigen p53	Homo sapiens (human)
B cell lineage commitment	Cellular tumor antigen p53	Homo sapiens (human)
T cell lineage commitment	Cellular tumor antigen p53	Homo sapiens (human)
response to ischemia	Cellular tumor antigen p53	Homo sapiens (human)
nucleotide-excision repair	Cellular tumor antigen p53	Homo sapiens (human)
double-strand break repair	Cellular tumor antigen p53	Homo sapiens (human)
regulation of DNA-templated transcription	Cellular tumor antigen p53	Homo sapiens (human)
regulation of transcription by RNA polymerase II	Cellular tumor antigen p53	Homo sapiens (human)
protein import into nucleus	Cellular tumor antigen p53	Homo sapiens (human)
autophagy	Cellular tumor antigen p53	Homo sapiens (human)
DNA damage response	Cellular tumor antigen p53	Homo sapiens (human)
DNA damage response, signal transduction by p53 class mediator resulting in cell cycle arrest	Cellular tumor antigen p53	Homo sapiens (human)
DNA damage response, signal transduction by p53 class mediator resulting in transcription of p21 class mediator	Cellular tumor antigen p53	Homo sapiens (human)
transforming growth factor beta receptor signaling pathway	Cellular tumor antigen p53	Homo sapiens (human)
Ras protein signal transduction	Cellular tumor antigen p53	Homo sapiens (human)
gastrulation	Cellular tumor antigen p53	Homo sapiens (human)
neuroblast proliferation	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of neuroblast proliferation	Cellular tumor antigen p53	Homo sapiens (human)
protein localization	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of DNA replication	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of cell population proliferation	Cellular tumor antigen p53	Homo sapiens (human)
determination of adult lifespan	Cellular tumor antigen p53	Homo sapiens (human)
mRNA transcription	Cellular tumor antigen p53	Homo sapiens (human)
rRNA transcription	Cellular tumor antigen p53	Homo sapiens (human)
response to salt stress	Cellular tumor antigen p53	Homo sapiens (human)
response to inorganic substance	Cellular tumor antigen p53	Homo sapiens (human)
response to X-ray	Cellular tumor antigen p53	Homo sapiens (human)
response to gamma radiation	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of gene expression	Cellular tumor antigen p53	Homo sapiens (human)
cardiac muscle cell apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of cardiac muscle cell apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
glial cell proliferation	Cellular tumor antigen p53	Homo sapiens (human)
viral process	Cellular tumor antigen p53	Homo sapiens (human)
glucose catabolic process to lactate via pyruvate	Cellular tumor antigen p53	Homo sapiens (human)
cerebellum development	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of cell growth	Cellular tumor antigen p53	Homo sapiens (human)
DNA damage response, signal transduction by p53 class mediator	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of transforming growth factor beta receptor signaling pathway	Cellular tumor antigen p53	Homo sapiens (human)
mitotic G1 DNA damage checkpoint signaling	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of telomere maintenance via telomerase	Cellular tumor antigen p53	Homo sapiens (human)
T cell differentiation in thymus	Cellular tumor antigen p53	Homo sapiens (human)
tumor necrosis factor-mediated signaling pathway	Cellular tumor antigen p53	Homo sapiens (human)
regulation of tissue remodeling	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to UV	Cellular tumor antigen p53	Homo sapiens (human)
multicellular organism growth	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of mitochondrial membrane permeability	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to glucose starvation	Cellular tumor antigen p53	Homo sapiens (human)
intrinsic apoptotic signaling pathway in response to DNA damage by p53 class mediator	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
entrainment of circadian clock by photoperiod	Cellular tumor antigen p53	Homo sapiens (human)
mitochondrial DNA repair	Cellular tumor antigen p53	Homo sapiens (human)
regulation of DNA damage response, signal transduction by p53 class mediator	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of neuron apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
transcription initiation-coupled chromatin remodeling	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of proteolysis	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of DNA-templated transcription	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of DNA-templated transcription	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of RNA polymerase II transcription preinitiation complex assembly	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of transcription by RNA polymerase II	Cellular tumor antigen p53	Homo sapiens (human)
response to antibiotic	Cellular tumor antigen p53	Homo sapiens (human)
fibroblast proliferation	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of fibroblast proliferation	Cellular tumor antigen p53	Homo sapiens (human)
circadian behavior	Cellular tumor antigen p53	Homo sapiens (human)
bone marrow development	Cellular tumor antigen p53	Homo sapiens (human)
embryonic organ development	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of peptidyl-tyrosine phosphorylation	Cellular tumor antigen p53	Homo sapiens (human)
protein stabilization	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of helicase activity	Cellular tumor antigen p53	Homo sapiens (human)
protein tetramerization	Cellular tumor antigen p53	Homo sapiens (human)
chromosome organization	Cellular tumor antigen p53	Homo sapiens (human)
neuron apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
regulation of cell cycle	Cellular tumor antigen p53	Homo sapiens (human)
hematopoietic stem cell differentiation	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of glial cell proliferation	Cellular tumor antigen p53	Homo sapiens (human)
type II interferon-mediated signaling pathway	Cellular tumor antigen p53	Homo sapiens (human)
cardiac septum morphogenesis	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of programmed necrotic cell death	Cellular tumor antigen p53	Homo sapiens (human)
protein-containing complex assembly	Cellular tumor antigen p53	Homo sapiens (human)
intrinsic apoptotic signaling pathway in response to endoplasmic reticulum stress	Cellular tumor antigen p53	Homo sapiens (human)
thymocyte apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of thymocyte apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
necroptotic process	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to hypoxia	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to xenobiotic stimulus	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to ionizing radiation	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to gamma radiation	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to UV-C	Cellular tumor antigen p53	Homo sapiens (human)
stem cell proliferation	Cellular tumor antigen p53	Homo sapiens (human)
signal transduction by p53 class mediator	Cellular tumor antigen p53	Homo sapiens (human)
intrinsic apoptotic signaling pathway by p53 class mediator	Cellular tumor antigen p53	Homo sapiens (human)
reactive oxygen species metabolic process	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to actinomycin D	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of release of cytochrome c from mitochondria	Cellular tumor antigen p53	Homo sapiens (human)
cellular senescence	Cellular tumor antigen p53	Homo sapiens (human)
replicative senescence	Cellular tumor antigen p53	Homo sapiens (human)
oxidative stress-induced premature senescence	Cellular tumor antigen p53	Homo sapiens (human)
intrinsic apoptotic signaling pathway	Cellular tumor antigen p53	Homo sapiens (human)
oligodendrocyte apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of execution phase of apoptosis	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of mitophagy	Cellular tumor antigen p53	Homo sapiens (human)
regulation of mitochondrial membrane permeability involved in apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
regulation of intrinsic apoptotic signaling pathway by p53 class mediator	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of miRNA transcription	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of G1 to G0 transition	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of miRNA processing	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of glucose catabolic process to lactate via pyruvate	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of pentose-phosphate shunt	Cellular tumor antigen p53	Homo sapiens (human)
intrinsic apoptotic signaling pathway in response to hypoxia	Cellular tumor antigen p53	Homo sapiens (human)
regulation of fibroblast apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of reactive oxygen species metabolic process	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of reactive oxygen species metabolic process	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of stem cell proliferation	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of cellular senescence	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of intrinsic apoptotic signaling pathway	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of low-density lipoprotein receptor activity	Integrin beta-3	Homo sapiens (human)
positive regulation of protein phosphorylation	Integrin beta-3	Homo sapiens (human)
positive regulation of endothelial cell proliferation	Integrin beta-3	Homo sapiens (human)
positive regulation of cell-matrix adhesion	Integrin beta-3	Homo sapiens (human)
cell-substrate junction assembly	Integrin beta-3	Homo sapiens (human)
cell adhesion	Integrin beta-3	Homo sapiens (human)
cell-matrix adhesion	Integrin beta-3	Homo sapiens (human)
integrin-mediated signaling pathway	Integrin beta-3	Homo sapiens (human)
embryo implantation	Integrin beta-3	Homo sapiens (human)
blood coagulation	Integrin beta-3	Homo sapiens (human)
positive regulation of endothelial cell migration	Integrin beta-3	Homo sapiens (human)
positive regulation of gene expression	Integrin beta-3	Homo sapiens (human)
negative regulation of macrophage derived foam cell differentiation	Integrin beta-3	Homo sapiens (human)
positive regulation of fibroblast migration	Integrin beta-3	Homo sapiens (human)
negative regulation of lipid storage	Integrin beta-3	Homo sapiens (human)
response to activity	Integrin beta-3	Homo sapiens (human)
smooth muscle cell migration	Integrin beta-3	Homo sapiens (human)
positive regulation of smooth muscle cell migration	Integrin beta-3	Homo sapiens (human)
platelet activation	Integrin beta-3	Homo sapiens (human)
positive regulation of vascular endothelial growth factor receptor signaling pathway	Integrin beta-3	Homo sapiens (human)
cell-substrate adhesion	Integrin beta-3	Homo sapiens (human)
activation of protein kinase activity	Integrin beta-3	Homo sapiens (human)
negative regulation of lipid transport	Integrin beta-3	Homo sapiens (human)
regulation of protein localization	Integrin beta-3	Homo sapiens (human)
regulation of actin cytoskeleton organization	Integrin beta-3	Homo sapiens (human)
cell adhesion mediated by integrin	Integrin beta-3	Homo sapiens (human)
positive regulation of cell adhesion mediated by integrin	Integrin beta-3	Homo sapiens (human)
positive regulation of osteoblast proliferation	Integrin beta-3	Homo sapiens (human)
heterotypic cell-cell adhesion	Integrin beta-3	Homo sapiens (human)
substrate adhesion-dependent cell spreading	Integrin beta-3	Homo sapiens (human)
tube development	Integrin beta-3	Homo sapiens (human)
wound healing, spreading of epidermal cells	Integrin beta-3	Homo sapiens (human)
cellular response to platelet-derived growth factor stimulus	Integrin beta-3	Homo sapiens (human)
apolipoprotein A-I-mediated signaling pathway	Integrin beta-3	Homo sapiens (human)
wound healing	Integrin beta-3	Homo sapiens (human)
apoptotic cell clearance	Integrin beta-3	Homo sapiens (human)
regulation of bone resorption	Integrin beta-3	Homo sapiens (human)
positive regulation of angiogenesis	Integrin beta-3	Homo sapiens (human)
positive regulation of bone resorption	Integrin beta-3	Homo sapiens (human)
symbiont entry into host cell	Integrin beta-3	Homo sapiens (human)
platelet-derived growth factor receptor signaling pathway	Integrin beta-3	Homo sapiens (human)
positive regulation of fibroblast proliferation	Integrin beta-3	Homo sapiens (human)
mesodermal cell differentiation	Integrin beta-3	Homo sapiens (human)
positive regulation of smooth muscle cell proliferation	Integrin beta-3	Homo sapiens (human)
positive regulation of peptidyl-tyrosine phosphorylation	Integrin beta-3	Homo sapiens (human)
negative regulation of lipoprotein metabolic process	Integrin beta-3	Homo sapiens (human)
negative chemotaxis	Integrin beta-3	Homo sapiens (human)
regulation of release of sequestered calcium ion into cytosol	Integrin beta-3	Homo sapiens (human)
regulation of serotonin uptake	Integrin beta-3	Homo sapiens (human)
angiogenesis involved in wound healing	Integrin beta-3	Homo sapiens (human)
positive regulation of ERK1 and ERK2 cascade	Integrin beta-3	Homo sapiens (human)
platelet aggregation	Integrin beta-3	Homo sapiens (human)
cellular response to mechanical stimulus	Integrin beta-3	Homo sapiens (human)
cellular response to xenobiotic stimulus	Integrin beta-3	Homo sapiens (human)
positive regulation of glomerular mesangial cell proliferation	Integrin beta-3	Homo sapiens (human)
blood coagulation, fibrin clot formation	Integrin beta-3	Homo sapiens (human)
maintenance of postsynaptic specialization structure	Integrin beta-3	Homo sapiens (human)
regulation of postsynaptic neurotransmitter receptor internalization	Integrin beta-3	Homo sapiens (human)
regulation of postsynaptic neurotransmitter receptor diffusion trapping	Integrin beta-3	Homo sapiens (human)
positive regulation of substrate adhesion-dependent cell spreading	Integrin beta-3	Homo sapiens (human)
positive regulation of adenylate cyclase-inhibiting opioid receptor signaling pathway	Integrin beta-3	Homo sapiens (human)
regulation of trophoblast cell migration	Integrin beta-3	Homo sapiens (human)
regulation of extracellular matrix organization	Integrin beta-3	Homo sapiens (human)
cellular response to insulin-like growth factor stimulus	Integrin beta-3	Homo sapiens (human)
negative regulation of endothelial cell apoptotic process	Integrin beta-3	Homo sapiens (human)
positive regulation of T cell migration	Integrin beta-3	Homo sapiens (human)
cell migration	Integrin beta-3	Homo sapiens (human)
angiogenesis	Plasminogen activator inhibitor 1	Homo sapiens (human)
regulation of signaling receptor activity	Plasminogen activator inhibitor 1	Homo sapiens (human)
negative regulation of plasminogen activation	Plasminogen activator inhibitor 1	Homo sapiens (human)
negative regulation of endopeptidase activity	Plasminogen activator inhibitor 1	Homo sapiens (human)
negative regulation of smooth muscle cell migration	Plasminogen activator inhibitor 1	Homo sapiens (human)
positive regulation of blood coagulation	Plasminogen activator inhibitor 1	Homo sapiens (human)
negative regulation of blood coagulation	Plasminogen activator inhibitor 1	Homo sapiens (human)
negative regulation of cell migration	Plasminogen activator inhibitor 1	Homo sapiens (human)
positive regulation of interleukin-8 production	Plasminogen activator inhibitor 1	Homo sapiens (human)
negative regulation of cell adhesion mediated by integrin	Plasminogen activator inhibitor 1	Homo sapiens (human)
positive regulation of leukotriene production involved in inflammatory response	Plasminogen activator inhibitor 1	Homo sapiens (human)
fibrinolysis	Plasminogen activator inhibitor 1	Homo sapiens (human)
positive regulation of angiogenesis	Plasminogen activator inhibitor 1	Homo sapiens (human)
positive regulation of receptor-mediated endocytosis	Plasminogen activator inhibitor 1	Homo sapiens (human)
positive regulation of inflammatory response	Plasminogen activator inhibitor 1	Homo sapiens (human)
defense response to Gram-negative bacterium	Plasminogen activator inhibitor 1	Homo sapiens (human)
negative regulation of fibrinolysis	Plasminogen activator inhibitor 1	Homo sapiens (human)
negative regulation of vascular wound healing	Plasminogen activator inhibitor 1	Homo sapiens (human)
negative regulation of wound healing	Plasminogen activator inhibitor 1	Homo sapiens (human)
cellular response to lipopolysaccharide	Plasminogen activator inhibitor 1	Homo sapiens (human)
positive regulation of monocyte chemotaxis	Plasminogen activator inhibitor 1	Homo sapiens (human)
replicative senescence	Plasminogen activator inhibitor 1	Homo sapiens (human)
dentinogenesis	Plasminogen activator inhibitor 1	Homo sapiens (human)
positive regulation of odontoblast differentiation	Plasminogen activator inhibitor 1	Homo sapiens (human)
negative regulation of extrinsic apoptotic signaling pathway via death domain receptors	Plasminogen activator inhibitor 1	Homo sapiens (human)
negative regulation of smooth muscle cell-matrix adhesion	Plasminogen activator inhibitor 1	Homo sapiens (human)
negative regulation of endothelial cell apoptotic process	Plasminogen activator inhibitor 1	Homo sapiens (human)
response to bacterium	Carbonic anhydrase 3	Homo sapiens (human)
one-carbon metabolic process	Carbonic anhydrase 3	Homo sapiens (human)
angiogenesis	72 kDa type IV collagenase	Homo sapiens (human)
ovarian follicle development	72 kDa type IV collagenase	Homo sapiens (human)
ovulation from ovarian follicle	72 kDa type IV collagenase	Homo sapiens (human)
luteinization	72 kDa type IV collagenase	Homo sapiens (human)
blood vessel maturation	72 kDa type IV collagenase	Homo sapiens (human)
intramembranous ossification	72 kDa type IV collagenase	Homo sapiens (human)
proteolysis	72 kDa type IV collagenase	Homo sapiens (human)
negative regulation of cell adhesion	72 kDa type IV collagenase	Homo sapiens (human)
heart development	72 kDa type IV collagenase	Homo sapiens (human)
embryo implantation	72 kDa type IV collagenase	Homo sapiens (human)
parturition	72 kDa type IV collagenase	Homo sapiens (human)
response to xenobiotic stimulus	72 kDa type IV collagenase	Homo sapiens (human)
response to mechanical stimulus	72 kDa type IV collagenase	Homo sapiens (human)
peripheral nervous system axon regeneration	72 kDa type IV collagenase	Homo sapiens (human)
response to activity	72 kDa type IV collagenase	Homo sapiens (human)
protein metabolic process	72 kDa type IV collagenase	Homo sapiens (human)
extracellular matrix disassembly	72 kDa type IV collagenase	Homo sapiens (human)
protein catabolic process	72 kDa type IV collagenase	Homo sapiens (human)
positive regulation of cell migration	72 kDa type IV collagenase	Homo sapiens (human)
collagen catabolic process	72 kDa type IV collagenase	Homo sapiens (human)
response to retinoic acid	72 kDa type IV collagenase	Homo sapiens (human)
cellular response to reactive oxygen species	72 kDa type IV collagenase	Homo sapiens (human)
response to nicotine	72 kDa type IV collagenase	Homo sapiens (human)
endodermal cell differentiation	72 kDa type IV collagenase	Homo sapiens (human)
response to hydrogen peroxide	72 kDa type IV collagenase	Homo sapiens (human)
response to estrogen	72 kDa type IV collagenase	Homo sapiens (human)
negative regulation of vasoconstriction	72 kDa type IV collagenase	Homo sapiens (human)
ephrin receptor signaling pathway	72 kDa type IV collagenase	Homo sapiens (human)
macrophage chemotaxis	72 kDa type IV collagenase	Homo sapiens (human)
response to electrical stimulus	72 kDa type IV collagenase	Homo sapiens (human)
response to hyperoxia	72 kDa type IV collagenase	Homo sapiens (human)
face morphogenesis	72 kDa type IV collagenase	Homo sapiens (human)
bone trabecula formation	72 kDa type IV collagenase	Homo sapiens (human)
prostate gland epithelium morphogenesis	72 kDa type IV collagenase	Homo sapiens (human)
cellular response to amino acid stimulus	72 kDa type IV collagenase	Homo sapiens (human)
cellular response to interleukin-1	72 kDa type IV collagenase	Homo sapiens (human)
cellular response to estradiol stimulus	72 kDa type IV collagenase	Homo sapiens (human)
cellular response to UV-A	72 kDa type IV collagenase	Homo sapiens (human)
cellular response to fluid shear stress	72 kDa type IV collagenase	Homo sapiens (human)
positive regulation of oxidative stress-induced neuron intrinsic apoptotic signaling pathway	72 kDa type IV collagenase	Homo sapiens (human)
response to amyloid-beta	72 kDa type IV collagenase	Homo sapiens (human)
positive regulation of vascular associated smooth muscle cell proliferation	72 kDa type IV collagenase	Homo sapiens (human)
extracellular matrix organization	72 kDa type IV collagenase	Homo sapiens (human)
response to hypoxia	72 kDa type IV collagenase	Homo sapiens (human)
tissue remodeling	72 kDa type IV collagenase	Homo sapiens (human)
positive regulation of leukocyte migration	Integrin alpha-IIb	Homo sapiens (human)
cell-matrix adhesion	Integrin alpha-IIb	Homo sapiens (human)
integrin-mediated signaling pathway	Integrin alpha-IIb	Homo sapiens (human)
angiogenesis	Integrin alpha-IIb	Homo sapiens (human)
cell-cell adhesion	Integrin alpha-IIb	Homo sapiens (human)
cell adhesion mediated by integrin	Integrin alpha-IIb	Homo sapiens (human)
membrane protein ectodomain proteolysis	Matrilysin	Homo sapiens (human)
membrane protein intracellular domain proteolysis	Matrilysin	Homo sapiens (human)
antibacterial peptide secretion	Matrilysin	Homo sapiens (human)
antibacterial peptide biosynthetic process	Matrilysin	Homo sapiens (human)
proteolysis	Matrilysin	Homo sapiens (human)
response to xenobiotic stimulus	Matrilysin	Homo sapiens (human)
extracellular matrix disassembly	Matrilysin	Homo sapiens (human)
positive regulation of cell migration	Matrilysin	Homo sapiens (human)
collagen catabolic process	Matrilysin	Homo sapiens (human)
regulation of cell population proliferation	Matrilysin	Homo sapiens (human)
defense response to Gram-negative bacterium	Matrilysin	Homo sapiens (human)
defense response to Gram-positive bacterium	Matrilysin	Homo sapiens (human)
extracellular matrix organization	Matrilysin	Homo sapiens (human)
response to hypoxia	Angiotensin-converting enzyme	Homo sapiens (human)
kidney development	Angiotensin-converting enzyme	Homo sapiens (human)
blood vessel remodeling	Angiotensin-converting enzyme	Homo sapiens (human)
angiotensin maturation	Angiotensin-converting enzyme	Homo sapiens (human)
regulation of renal output by angiotensin	Angiotensin-converting enzyme	Homo sapiens (human)
neutrophil mediated immunity	Angiotensin-converting enzyme	Homo sapiens (human)
antigen processing and presentation of peptide antigen via MHC class I	Angiotensin-converting enzyme	Homo sapiens (human)
regulation of systemic arterial blood pressure by renin-angiotensin	Angiotensin-converting enzyme	Homo sapiens (human)
proteolysis	Angiotensin-converting enzyme	Homo sapiens (human)
spermatogenesis	Angiotensin-converting enzyme	Homo sapiens (human)
female pregnancy	Angiotensin-converting enzyme	Homo sapiens (human)
regulation of blood pressure	Angiotensin-converting enzyme	Homo sapiens (human)
male gonad development	Angiotensin-converting enzyme	Homo sapiens (human)
response to xenobiotic stimulus	Angiotensin-converting enzyme	Homo sapiens (human)
embryo development ending in birth or egg hatching	Angiotensin-converting enzyme	Homo sapiens (human)
post-transcriptional regulation of gene expression	Angiotensin-converting enzyme	Homo sapiens (human)
negative regulation of gene expression	Angiotensin-converting enzyme	Homo sapiens (human)
substance P catabolic process	Angiotensin-converting enzyme	Homo sapiens (human)
bradykinin catabolic process	Angiotensin-converting enzyme	Homo sapiens (human)
regulation of smooth muscle cell migration	Angiotensin-converting enzyme	Homo sapiens (human)
regulation of vasoconstriction	Angiotensin-converting enzyme	Homo sapiens (human)
animal organ regeneration	Angiotensin-converting enzyme	Homo sapiens (human)
response to nutrient levels	Angiotensin-converting enzyme	Homo sapiens (human)
response to lipopolysaccharide	Angiotensin-converting enzyme	Homo sapiens (human)
mononuclear cell proliferation	Angiotensin-converting enzyme	Homo sapiens (human)
response to laminar fluid shear stress	Angiotensin-converting enzyme	Homo sapiens (human)
angiotensin-activated signaling pathway	Angiotensin-converting enzyme	Homo sapiens (human)
vasoconstriction	Angiotensin-converting enzyme	Homo sapiens (human)
hormone metabolic process	Angiotensin-converting enzyme	Homo sapiens (human)
hormone catabolic process	Angiotensin-converting enzyme	Homo sapiens (human)
eating behavior	Angiotensin-converting enzyme	Homo sapiens (human)
positive regulation of apoptotic process	Angiotensin-converting enzyme	Homo sapiens (human)
peptide catabolic process	Angiotensin-converting enzyme	Homo sapiens (human)
positive regulation of vasoconstriction	Angiotensin-converting enzyme	Homo sapiens (human)
negative regulation of glucose import	Angiotensin-converting enzyme	Homo sapiens (human)
regulation of synaptic plasticity	Angiotensin-converting enzyme	Homo sapiens (human)
lung alveolus development	Angiotensin-converting enzyme	Homo sapiens (human)
amyloid-beta metabolic process	Angiotensin-converting enzyme	Homo sapiens (human)
arachidonic acid secretion	Angiotensin-converting enzyme	Homo sapiens (human)
positive regulation of neurogenesis	Angiotensin-converting enzyme	Homo sapiens (human)
heart contraction	Angiotensin-converting enzyme	Homo sapiens (human)
regulation of angiotensin metabolic process	Angiotensin-converting enzyme	Homo sapiens (human)
hematopoietic stem cell differentiation	Angiotensin-converting enzyme	Homo sapiens (human)
angiogenesis involved in coronary vascular morphogenesis	Angiotensin-converting enzyme	Homo sapiens (human)
cellular response to glucose stimulus	Angiotensin-converting enzyme	Homo sapiens (human)
response to dexamethasone	Angiotensin-converting enzyme	Homo sapiens (human)
cell proliferation in bone marrow	Angiotensin-converting enzyme	Homo sapiens (human)
regulation of heart rate by cardiac conduction	Angiotensin-converting enzyme	Homo sapiens (human)
negative regulation of calcium ion import	Angiotensin-converting enzyme	Homo sapiens (human)
response to thyroid hormone	Angiotensin-converting enzyme	Homo sapiens (human)
blood vessel diameter maintenance	Angiotensin-converting enzyme	Homo sapiens (human)
regulation of hematopoietic stem cell proliferation	Angiotensin-converting enzyme	Homo sapiens (human)
negative regulation of gap junction assembly	Angiotensin-converting enzyme	Homo sapiens (human)
cellular response to aldosterone	Angiotensin-converting enzyme	Homo sapiens (human)
positive regulation of peptidyl-cysteine S-nitrosylation	Angiotensin-converting enzyme	Homo sapiens (human)
positive regulation of systemic arterial blood pressure	Angiotensin-converting enzyme	Homo sapiens (human)
cell adhesion	L-selectin	Homo sapiens (human)
leukocyte cell-cell adhesion	L-selectin	Homo sapiens (human)
calcium-dependent cell-cell adhesion via plasma membrane cell adhesion molecules	L-selectin	Homo sapiens (human)
leukocyte tethering or rolling	L-selectin	Homo sapiens (human)
heterophilic cell-cell adhesion via plasma membrane cell adhesion molecules	L-selectin	Homo sapiens (human)
response to cytokine	L-selectin	Homo sapiens (human)
positive regulation of leukocyte migration	P-selectin	Homo sapiens (human)
inflammatory response	P-selectin	Homo sapiens (human)
cell adhesion	P-selectin	Homo sapiens (human)
leukocyte cell-cell adhesion	P-selectin	Homo sapiens (human)
positive regulation of platelet activation	P-selectin	Homo sapiens (human)
calcium-dependent cell-cell adhesion via plasma membrane cell adhesion molecules	P-selectin	Homo sapiens (human)
response to lipopolysaccharide	P-selectin	Homo sapiens (human)
regulation of integrin activation	P-selectin	Homo sapiens (human)
defense response to Gram-negative bacterium	P-selectin	Homo sapiens (human)
leukocyte tethering or rolling	P-selectin	Homo sapiens (human)
positive regulation of phosphatidylinositol 3-kinase/protein kinase B signal transduction	P-selectin	Homo sapiens (human)
cell-cell adhesion	P-selectin	Homo sapiens (human)
positive regulation of leukocyte tethering or rolling	P-selectin	Homo sapiens (human)
response to cytokine	P-selectin	Homo sapiens (human)
heterophilic cell-cell adhesion via plasma membrane cell adhesion molecules	P-selectin	Homo sapiens (human)
positive regulation of receptor internalization	E-selectin	Homo sapiens (human)
leukocyte migration involved in inflammatory response	E-selectin	Homo sapiens (human)
positive regulation of leukocyte migration	E-selectin	Homo sapiens (human)
inflammatory response	E-selectin	Homo sapiens (human)
heterophilic cell-cell adhesion via plasma membrane cell adhesion molecules	E-selectin	Homo sapiens (human)
leukocyte cell-cell adhesion	E-selectin	Homo sapiens (human)
activation of phospholipase C activity	E-selectin	Homo sapiens (human)
calcium-mediated signaling	E-selectin	Homo sapiens (human)
actin filament-based process	E-selectin	Homo sapiens (human)
response to lipopolysaccharide	E-selectin	Homo sapiens (human)
response to tumor necrosis factor	E-selectin	Homo sapiens (human)
regulation of inflammatory response	E-selectin	Homo sapiens (human)
leukocyte tethering or rolling	E-selectin	Homo sapiens (human)
response to interleukin-1	E-selectin	Homo sapiens (human)
positive regulation of leukocyte tethering or rolling	E-selectin	Homo sapiens (human)
response to cytokine	E-selectin	Homo sapiens (human)
peptidyl-proline hydroxylation to 4-hydroxy-L-proline	Prolyl 4-hydroxylase subunit alpha-1	Gallus gallus (chicken)
bicarbonate transport	Carbonic anhydrase 4	Homo sapiens (human)
one-carbon metabolic process	Carbonic anhydrase 4	Homo sapiens (human)
detection of chemical stimulus involved in sensory perception of bitter taste	Carbonic anhydrase 6	Homo sapiens (human)
one-carbon metabolic process	Carbonic anhydrase 6	Homo sapiens (human)
behavioral fear response	Dipeptidyl peptidase 4	Homo sapiens (human)
response to hypoxia	Dipeptidyl peptidase 4	Homo sapiens (human)
proteolysis	Dipeptidyl peptidase 4	Homo sapiens (human)
cell adhesion	Dipeptidyl peptidase 4	Homo sapiens (human)
positive regulation of cell population proliferation	Dipeptidyl peptidase 4	Homo sapiens (human)
negative regulation of extracellular matrix disassembly	Dipeptidyl peptidase 4	Homo sapiens (human)
peptide hormone processing	Dipeptidyl peptidase 4	Homo sapiens (human)
receptor-mediated endocytosis of virus by host cell	Dipeptidyl peptidase 4	Homo sapiens (human)
T cell costimulation	Dipeptidyl peptidase 4	Homo sapiens (human)
regulation of cell-cell adhesion mediated by integrin	Dipeptidyl peptidase 4	Homo sapiens (human)
locomotory exploration behavior	Dipeptidyl peptidase 4	Homo sapiens (human)
psychomotor behavior	Dipeptidyl peptidase 4	Homo sapiens (human)
T cell activation	Dipeptidyl peptidase 4	Homo sapiens (human)
endothelial cell migration	Dipeptidyl peptidase 4	Homo sapiens (human)
symbiont entry into host cell	Dipeptidyl peptidase 4	Homo sapiens (human)
receptor-mediated virion attachment to host cell	Dipeptidyl peptidase 4	Homo sapiens (human)
negative chemotaxis	Dipeptidyl peptidase 4	Homo sapiens (human)
membrane fusion	Dipeptidyl peptidase 4	Homo sapiens (human)
negative regulation of neutrophil chemotaxis	Dipeptidyl peptidase 4	Homo sapiens (human)
glucagon processing	Dipeptidyl peptidase 4	Homo sapiens (human)
proteolysis	Proteasome subunit beta type-5	Homo sapiens (human)
response to oxidative stress	Proteasome subunit beta type-5	Homo sapiens (human)
proteasome-mediated ubiquitin-dependent protein catabolic process	Proteasome subunit beta type-5	Homo sapiens (human)
one-carbon metabolic process	Carbonic anhydrase 5A, mitochondrial	Homo sapiens (human)
calcium ion homeostasis	Alpha-synuclein	Homo sapiens (human)
negative regulation of transcription by RNA polymerase II	Alpha-synuclein	Homo sapiens (human)
microglial cell activation	Alpha-synuclein	Homo sapiens (human)
positive regulation of receptor recycling	Alpha-synuclein	Homo sapiens (human)
positive regulation of neurotransmitter secretion	Alpha-synuclein	Homo sapiens (human)
negative regulation of protein kinase activity	Alpha-synuclein	Homo sapiens (human)
fatty acid metabolic process	Alpha-synuclein	Homo sapiens (human)
neutral lipid metabolic process	Alpha-synuclein	Homo sapiens (human)
phospholipid metabolic process	Alpha-synuclein	Homo sapiens (human)
activation of cysteine-type endopeptidase activity involved in apoptotic process	Alpha-synuclein	Homo sapiens (human)
mitochondrial membrane organization	Alpha-synuclein	Homo sapiens (human)
adult locomotory behavior	Alpha-synuclein	Homo sapiens (human)
response to xenobiotic stimulus	Alpha-synuclein	Homo sapiens (human)
response to iron(II) ion	Alpha-synuclein	Homo sapiens (human)
regulation of phospholipase activity	Alpha-synuclein	Homo sapiens (human)
negative regulation of platelet-derived growth factor receptor signaling pathway	Alpha-synuclein	Homo sapiens (human)
regulation of glutamate secretion	Alpha-synuclein	Homo sapiens (human)
regulation of dopamine secretion	Alpha-synuclein	Homo sapiens (human)
synaptic vesicle exocytosis	Alpha-synuclein	Homo sapiens (human)
synaptic vesicle priming	Alpha-synuclein	Homo sapiens (human)
regulation of transmembrane transporter activity	Alpha-synuclein	Homo sapiens (human)
negative regulation of microtubule polymerization	Alpha-synuclein	Homo sapiens (human)
receptor internalization	Alpha-synuclein	Homo sapiens (human)
protein destabilization	Alpha-synuclein	Homo sapiens (human)
response to magnesium ion	Alpha-synuclein	Homo sapiens (human)
negative regulation of transporter activity	Alpha-synuclein	Homo sapiens (human)
response to lipopolysaccharide	Alpha-synuclein	Homo sapiens (human)
negative regulation of monooxygenase activity	Alpha-synuclein	Homo sapiens (human)
positive regulation of peptidyl-serine phosphorylation	Alpha-synuclein	Homo sapiens (human)
response to type II interferon	Alpha-synuclein	Homo sapiens (human)
cellular response to oxidative stress	Alpha-synuclein	Homo sapiens (human)
SNARE complex assembly	Alpha-synuclein	Homo sapiens (human)
positive regulation of SNARE complex assembly	Alpha-synuclein	Homo sapiens (human)
regulation of locomotion	Alpha-synuclein	Homo sapiens (human)
dopamine biosynthetic process	Alpha-synuclein	Homo sapiens (human)
mitochondrial ATP synthesis coupled electron transport	Alpha-synuclein	Homo sapiens (human)
regulation of macrophage activation	Alpha-synuclein	Homo sapiens (human)

Process	via Protein(s)	Taxonomy
zinc ion binding	Carbonic anhydrase 12	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 12	Homo sapiens (human)
serine-type endopeptidase activity	Urokinase-type plasminogen activator	Homo sapiens (human)
protein binding	Urokinase-type plasminogen activator	Homo sapiens (human)
serine-type endopeptidase activity	Tissue-type plasminogen activator	Homo sapiens (human)
signaling receptor binding	Tissue-type plasminogen activator	Homo sapiens (human)
protein binding	Tissue-type plasminogen activator	Homo sapiens (human)
phosphoprotein binding	Tissue-type plasminogen activator	Homo sapiens (human)
arylesterase activity	Carbonic anhydrase 1	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 1	Homo sapiens (human)
protein binding	Carbonic anhydrase 1	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 1	Homo sapiens (human)
hydro-lyase activity	Carbonic anhydrase 1	Homo sapiens (human)
cyanamide hydratase activity	Carbonic anhydrase 1	Homo sapiens (human)
arylesterase activity	Carbonic anhydrase 2	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 2	Homo sapiens (human)
protein binding	Carbonic anhydrase 2	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 2	Homo sapiens (human)
cyanamide hydratase activity	Carbonic anhydrase 2	Homo sapiens (human)
transcription cis-regulatory region binding	Cellular tumor antigen p53	Homo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA binding	Cellular tumor antigen p53	Homo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specific	Cellular tumor antigen p53	Homo sapiens (human)
cis-regulatory region sequence-specific DNA binding	Cellular tumor antigen p53	Homo sapiens (human)
core promoter sequence-specific DNA binding	Cellular tumor antigen p53	Homo sapiens (human)
TFIID-class transcription factor complex binding	Cellular tumor antigen p53	Homo sapiens (human)
DNA-binding transcription repressor activity, RNA polymerase II-specific	Cellular tumor antigen p53	Homo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specific	Cellular tumor antigen p53	Homo sapiens (human)
protease binding	Cellular tumor antigen p53	Homo sapiens (human)
p53 binding	Cellular tumor antigen p53	Homo sapiens (human)
DNA binding	Cellular tumor antigen p53	Homo sapiens (human)
chromatin binding	Cellular tumor antigen p53	Homo sapiens (human)
DNA-binding transcription factor activity	Cellular tumor antigen p53	Homo sapiens (human)
mRNA 3'-UTR binding	Cellular tumor antigen p53	Homo sapiens (human)
copper ion binding	Cellular tumor antigen p53	Homo sapiens (human)
protein binding	Cellular tumor antigen p53	Homo sapiens (human)
zinc ion binding	Cellular tumor antigen p53	Homo sapiens (human)
enzyme binding	Cellular tumor antigen p53	Homo sapiens (human)
receptor tyrosine kinase binding	Cellular tumor antigen p53	Homo sapiens (human)
ubiquitin protein ligase binding	Cellular tumor antigen p53	Homo sapiens (human)
histone deacetylase regulator activity	Cellular tumor antigen p53	Homo sapiens (human)
ATP-dependent DNA/DNA annealing activity	Cellular tumor antigen p53	Homo sapiens (human)
identical protein binding	Cellular tumor antigen p53	Homo sapiens (human)
histone deacetylase binding	Cellular tumor antigen p53	Homo sapiens (human)
protein heterodimerization activity	Cellular tumor antigen p53	Homo sapiens (human)
protein-folding chaperone binding	Cellular tumor antigen p53	Homo sapiens (human)
protein phosphatase 2A binding	Cellular tumor antigen p53	Homo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor binding	Cellular tumor antigen p53	Homo sapiens (human)
14-3-3 protein binding	Cellular tumor antigen p53	Homo sapiens (human)
MDM2/MDM4 family protein binding	Cellular tumor antigen p53	Homo sapiens (human)
disordered domain specific binding	Cellular tumor antigen p53	Homo sapiens (human)
general transcription initiation factor binding	Cellular tumor antigen p53	Homo sapiens (human)
molecular function activator activity	Cellular tumor antigen p53	Homo sapiens (human)
promoter-specific chromatin binding	Cellular tumor antigen p53	Homo sapiens (human)
fibroblast growth factor binding	Integrin beta-3	Homo sapiens (human)
C-X3-C chemokine binding	Integrin beta-3	Homo sapiens (human)
insulin-like growth factor I binding	Integrin beta-3	Homo sapiens (human)
neuregulin binding	Integrin beta-3	Homo sapiens (human)
virus receptor activity	Integrin beta-3	Homo sapiens (human)
fibronectin binding	Integrin beta-3	Homo sapiens (human)
protease binding	Integrin beta-3	Homo sapiens (human)
protein disulfide isomerase activity	Integrin beta-3	Homo sapiens (human)
protein kinase C binding	Integrin beta-3	Homo sapiens (human)
platelet-derived growth factor receptor binding	Integrin beta-3	Homo sapiens (human)
integrin binding	Integrin beta-3	Homo sapiens (human)
protein binding	Integrin beta-3	Homo sapiens (human)
coreceptor activity	Integrin beta-3	Homo sapiens (human)
enzyme binding	Integrin beta-3	Homo sapiens (human)
identical protein binding	Integrin beta-3	Homo sapiens (human)
vascular endothelial growth factor receptor 2 binding	Integrin beta-3	Homo sapiens (human)
metal ion binding	Integrin beta-3	Homo sapiens (human)
cell adhesion molecule binding	Integrin beta-3	Homo sapiens (human)
extracellular matrix binding	Integrin beta-3	Homo sapiens (human)
fibrinogen binding	Integrin beta-3	Homo sapiens (human)
protease binding	Plasminogen activator inhibitor 1	Homo sapiens (human)
serine-type endopeptidase inhibitor activity	Plasminogen activator inhibitor 1	Homo sapiens (human)
signaling receptor binding	Plasminogen activator inhibitor 1	Homo sapiens (human)
protein binding	Plasminogen activator inhibitor 1	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 3	Homo sapiens (human)
protein binding	Carbonic anhydrase 3	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 3	Homo sapiens (human)
nickel cation binding	Carbonic anhydrase 3	Homo sapiens (human)
fibronectin binding	72 kDa type IV collagenase	Homo sapiens (human)
endopeptidase activity	72 kDa type IV collagenase	Homo sapiens (human)
metalloendopeptidase activity	72 kDa type IV collagenase	Homo sapiens (human)
serine-type endopeptidase activity	72 kDa type IV collagenase	Homo sapiens (human)
protein binding	72 kDa type IV collagenase	Homo sapiens (human)
metallopeptidase activity	72 kDa type IV collagenase	Homo sapiens (human)
zinc ion binding	72 kDa type IV collagenase	Homo sapiens (human)
protein binding	Integrin alpha-IIb	Homo sapiens (human)
identical protein binding	Integrin alpha-IIb	Homo sapiens (human)
metal ion binding	Integrin alpha-IIb	Homo sapiens (human)
extracellular matrix binding	Integrin alpha-IIb	Homo sapiens (human)
molecular adaptor activity	Integrin alpha-IIb	Homo sapiens (human)
fibrinogen binding	Integrin alpha-IIb	Homo sapiens (human)
integrin binding	Integrin alpha-IIb	Homo sapiens (human)
endopeptidase activity	Matrilysin	Homo sapiens (human)
metalloendopeptidase activity	Matrilysin	Homo sapiens (human)
serine-type endopeptidase activity	Matrilysin	Homo sapiens (human)
protein binding	Matrilysin	Homo sapiens (human)
metallopeptidase activity	Matrilysin	Homo sapiens (human)
zinc ion binding	Matrilysin	Homo sapiens (human)
endopeptidase activity	Angiotensin-converting enzyme	Homo sapiens (human)
carboxypeptidase activity	Angiotensin-converting enzyme	Homo sapiens (human)
metalloendopeptidase activity	Angiotensin-converting enzyme	Homo sapiens (human)
calmodulin binding	Angiotensin-converting enzyme	Homo sapiens (human)
peptidase activity	Angiotensin-converting enzyme	Homo sapiens (human)
metallopeptidase activity	Angiotensin-converting enzyme	Homo sapiens (human)
exopeptidase activity	Angiotensin-converting enzyme	Homo sapiens (human)
tripeptidyl-peptidase activity	Angiotensin-converting enzyme	Homo sapiens (human)
peptidyl-dipeptidase activity	Angiotensin-converting enzyme	Homo sapiens (human)
zinc ion binding	Angiotensin-converting enzyme	Homo sapiens (human)
chloride ion binding	Angiotensin-converting enzyme	Homo sapiens (human)
mitogen-activated protein kinase kinase binding	Angiotensin-converting enzyme	Homo sapiens (human)
bradykinin receptor binding	Angiotensin-converting enzyme	Homo sapiens (human)
mitogen-activated protein kinase binding	Angiotensin-converting enzyme	Homo sapiens (human)
metallodipeptidase activity	Angiotensin-converting enzyme	Homo sapiens (human)
heterocyclic compound binding	Angiotensin-converting enzyme	Homo sapiens (human)
protease binding	L-selectin	Homo sapiens (human)
calcium ion binding	L-selectin	Homo sapiens (human)
protein binding	L-selectin	Homo sapiens (human)
heparin binding	L-selectin	Homo sapiens (human)
carbohydrate binding	L-selectin	Homo sapiens (human)
glycosphingolipid binding	L-selectin	Homo sapiens (human)
oligosaccharide binding	L-selectin	Homo sapiens (human)
sialic acid binding	L-selectin	Homo sapiens (human)
lipopolysaccharide binding	P-selectin	Homo sapiens (human)
integrin binding	P-selectin	Homo sapiens (human)
calcium ion binding	P-selectin	Homo sapiens (human)
protein binding	P-selectin	Homo sapiens (human)
heparin binding	P-selectin	Homo sapiens (human)
sialic acid binding	P-selectin	Homo sapiens (human)
fucose binding	P-selectin	Homo sapiens (human)
glycosphingolipid binding	P-selectin	Homo sapiens (human)
calcium-dependent protein binding	P-selectin	Homo sapiens (human)
oligosaccharide binding	P-selectin	Homo sapiens (human)
transmembrane signaling receptor activity	E-selectin	Homo sapiens (human)
protein binding	E-selectin	Homo sapiens (human)
sialic acid binding	E-selectin	Homo sapiens (human)
phospholipase binding	E-selectin	Homo sapiens (human)
metal ion binding	E-selectin	Homo sapiens (human)
oligosaccharide binding	E-selectin	Homo sapiens (human)
procollagen-proline 4-dioxygenase activity	Prolyl 4-hydroxylase subunit alpha-1	Gallus gallus (chicken)
iron ion binding	Prolyl 4-hydroxylase subunit alpha-1	Gallus gallus (chicken)
L-ascorbic acid binding	Prolyl 4-hydroxylase subunit alpha-1	Gallus gallus (chicken)
protein binding	Carbonic anhydrase 4	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 4	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 4	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 6	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 6	Homo sapiens (human)
virus receptor activity	Dipeptidyl peptidase 4	Homo sapiens (human)
protease binding	Dipeptidyl peptidase 4	Homo sapiens (human)
aminopeptidase activity	Dipeptidyl peptidase 4	Homo sapiens (human)
serine-type endopeptidase activity	Dipeptidyl peptidase 4	Homo sapiens (human)
signaling receptor binding	Dipeptidyl peptidase 4	Homo sapiens (human)
protein binding	Dipeptidyl peptidase 4	Homo sapiens (human)
serine-type peptidase activity	Dipeptidyl peptidase 4	Homo sapiens (human)
dipeptidyl-peptidase activity	Dipeptidyl peptidase 4	Homo sapiens (human)
identical protein binding	Dipeptidyl peptidase 4	Homo sapiens (human)
protein homodimerization activity	Dipeptidyl peptidase 4	Homo sapiens (human)
chemorepellent activity	Dipeptidyl peptidase 4	Homo sapiens (human)
threonine-type endopeptidase activity	Proteasome subunit beta type-5	Homo sapiens (human)
protein binding	Proteasome subunit beta type-5	Homo sapiens (human)
peptidase activity	Proteasome subunit beta type-5	Homo sapiens (human)
endopeptidase activity	Proteasome subunit beta type-5	Homo sapiens (human)
G protein-coupled adenosine receptor activity	Adenosine receptor A2a	Rattus norvegicus (Norway rat)
carbonate dehydratase activity	Carbonic anhydrase 5A, mitochondrial	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 5A, mitochondrial	Homo sapiens (human)
fatty acid binding	Alpha-synuclein	Homo sapiens (human)
phospholipase D inhibitor activity	Alpha-synuclein	Homo sapiens (human)
SNARE binding	Alpha-synuclein	Homo sapiens (human)
magnesium ion binding	Alpha-synuclein	Homo sapiens (human)
transcription cis-regulatory region binding	Alpha-synuclein	Homo sapiens (human)
actin binding	Alpha-synuclein	Homo sapiens (human)
protein kinase inhibitor activity	Alpha-synuclein	Homo sapiens (human)
copper ion binding	Alpha-synuclein	Homo sapiens (human)
calcium ion binding	Alpha-synuclein	Homo sapiens (human)
protein binding	Alpha-synuclein	Homo sapiens (human)
phospholipid binding	Alpha-synuclein	Homo sapiens (human)
ferrous iron binding	Alpha-synuclein	Homo sapiens (human)
zinc ion binding	Alpha-synuclein	Homo sapiens (human)
lipid binding	Alpha-synuclein	Homo sapiens (human)
oxidoreductase activity	Alpha-synuclein	Homo sapiens (human)
kinesin binding	Alpha-synuclein	Homo sapiens (human)
Hsp70 protein binding	Alpha-synuclein	Homo sapiens (human)
histone binding	Alpha-synuclein	Homo sapiens (human)
identical protein binding	Alpha-synuclein	Homo sapiens (human)
alpha-tubulin binding	Alpha-synuclein	Homo sapiens (human)
cysteine-type endopeptidase inhibitor activity involved in apoptotic process	Alpha-synuclein	Homo sapiens (human)
tau protein binding	Alpha-synuclein	Homo sapiens (human)
phosphoprotein binding	Alpha-synuclein	Homo sapiens (human)
molecular adaptor activity	Alpha-synuclein	Homo sapiens (human)
dynein complex binding	Alpha-synuclein	Homo sapiens (human)
cuprous ion binding	Alpha-synuclein	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 7	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 7	Homo sapiens (human)
fucosyltransferase activity	4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT6	Homo sapiens (human)
4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase activity	4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT6	Homo sapiens (human)
alpha-(1->3)-fucosyltransferase activity	4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT6	Homo sapiens (human)
protein binding	Anthrax toxin receptor 2	Homo sapiens (human)
metal ion binding	Anthrax toxin receptor 2	Homo sapiens (human)
transmembrane signaling receptor activity	Anthrax toxin receptor 2	Homo sapiens (human)
endopeptidase activity	Disintegrin and metalloproteinase domain-containing protein 17	Homo sapiens (human)
metalloendopeptidase activity	Disintegrin and metalloproteinase domain-containing protein 17	Homo sapiens (human)
Notch binding	Disintegrin and metalloproteinase domain-containing protein 17	Homo sapiens (human)
interleukin-6 receptor binding	Disintegrin and metalloproteinase domain-containing protein 17	Homo sapiens (human)
integrin binding	Disintegrin and metalloproteinase domain-containing protein 17	Homo sapiens (human)
protein binding	Disintegrin and metalloproteinase domain-containing protein 17	Homo sapiens (human)
peptidase activity	Disintegrin and metalloproteinase domain-containing protein 17	Homo sapiens (human)
metallopeptidase activity	Disintegrin and metalloproteinase domain-containing protein 17	Homo sapiens (human)
SH3 domain binding	Disintegrin and metalloproteinase domain-containing protein 17	Homo sapiens (human)
cytokine binding	Disintegrin and metalloproteinase domain-containing protein 17	Homo sapiens (human)
PDZ domain binding	Disintegrin and metalloproteinase domain-containing protein 17	Homo sapiens (human)
tumor necrosis factor binding	Disintegrin and metalloproteinase domain-containing protein 17	Homo sapiens (human)
metal ion binding	Disintegrin and metalloproteinase domain-containing protein 17	Homo sapiens (human)
metalloendopeptidase activity involved in amyloid precursor protein catabolic process	Disintegrin and metalloproteinase domain-containing protein 17	Homo sapiens (human)
peroxidase activity	Lactoperoxidase	Bos taurus (cattle)
calcium ion binding	Lactoperoxidase	Bos taurus (cattle)
heme binding	Lactoperoxidase	Bos taurus (cattle)
thiocyanate peroxidase activity	Lactoperoxidase	Bos taurus (cattle)
lactoperoxidase activity	Lactoperoxidase	Bos taurus (cattle)
polypeptide N-acetylgalactosaminyltransferase activity	Polypeptide N-acetylgalactosaminyltransferase 2	Homo sapiens (human)
protein binding	Polypeptide N-acetylgalactosaminyltransferase 2	Homo sapiens (human)
manganese ion binding	Polypeptide N-acetylgalactosaminyltransferase 2	Homo sapiens (human)
carbohydrate binding	Polypeptide N-acetylgalactosaminyltransferase 2	Homo sapiens (human)
protein binding	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
fucosyltransferase activity	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase activity	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
alpha-(1->3)-fucosyltransferase activity	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
beta-galactoside (CMP) alpha-2,3-sialyltransferase activity	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)
sialyltransferase activity	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)
beta-D-galactosyl-(1->3)-N-acetyl-beta-D-galactosaminide alpha-2,3- sialyltransferase	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 9	Homo sapiens (human)
protein binding	Carbonic anhydrase 9	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 9	Homo sapiens (human)
molecular function activator activity	Carbonic anhydrase 9	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 14	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 14	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 5B, mitochondrial	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 5B, mitochondrial	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
plasma membrane	Carbonic anhydrase 12	Homo sapiens (human)
membrane	Carbonic anhydrase 12	Homo sapiens (human)
basolateral plasma membrane	Carbonic anhydrase 12	Homo sapiens (human)
apical plasma membrane	Carbonic anhydrase 12	Homo sapiens (human)
plasma membrane	Carbonic anhydrase 12	Homo sapiens (human)
extracellular region	Urokinase-type plasminogen activator	Homo sapiens (human)
extracellular space	Urokinase-type plasminogen activator	Homo sapiens (human)
plasma membrane	Urokinase-type plasminogen activator	Homo sapiens (human)
focal adhesion	Urokinase-type plasminogen activator	Homo sapiens (human)
external side of plasma membrane	Urokinase-type plasminogen activator	Homo sapiens (human)
cell surface	Urokinase-type plasminogen activator	Homo sapiens (human)
specific granule membrane	Urokinase-type plasminogen activator	Homo sapiens (human)
extracellular exosome	Urokinase-type plasminogen activator	Homo sapiens (human)
tertiary granule membrane	Urokinase-type plasminogen activator	Homo sapiens (human)
serine protease inhibitor complex	Urokinase-type plasminogen activator	Homo sapiens (human)
protein complex involved in cell-matrix adhesion	Urokinase-type plasminogen activator	Homo sapiens (human)
serine-type endopeptidase complex	Urokinase-type plasminogen activator	Homo sapiens (human)
extracellular space	Urokinase-type plasminogen activator	Homo sapiens (human)
collagen-containing extracellular matrix	Tissue-type plasminogen activator	Homo sapiens (human)
extracellular region	Tissue-type plasminogen activator	Homo sapiens (human)
cytoplasm	Tissue-type plasminogen activator	Homo sapiens (human)
cell surface	Tissue-type plasminogen activator	Homo sapiens (human)
secretory granule	Tissue-type plasminogen activator	Homo sapiens (human)
apical part of cell	Tissue-type plasminogen activator	Homo sapiens (human)
extracellular exosome	Tissue-type plasminogen activator	Homo sapiens (human)
serine protease inhibitor complex	Tissue-type plasminogen activator	Homo sapiens (human)
Schaffer collateral - CA1 synapse	Tissue-type plasminogen activator	Homo sapiens (human)
glutamatergic synapse	Tissue-type plasminogen activator	Homo sapiens (human)
extracellular space	Tissue-type plasminogen activator	Homo sapiens (human)
cytosol	Carbonic anhydrase 1	Homo sapiens (human)
extracellular exosome	Carbonic anhydrase 1	Homo sapiens (human)
cytoplasm	Carbonic anhydrase 2	Homo sapiens (human)
cytosol	Carbonic anhydrase 2	Homo sapiens (human)
plasma membrane	Carbonic anhydrase 2	Homo sapiens (human)
myelin sheath	Carbonic anhydrase 2	Homo sapiens (human)
apical part of cell	Carbonic anhydrase 2	Homo sapiens (human)
extracellular exosome	Carbonic anhydrase 2	Homo sapiens (human)
cytoplasm	Carbonic anhydrase 2	Homo sapiens (human)
plasma membrane	Carbonic anhydrase 2	Homo sapiens (human)
apical part of cell	Carbonic anhydrase 2	Homo sapiens (human)
nuclear body	Cellular tumor antigen p53	Homo sapiens (human)
nucleus	Cellular tumor antigen p53	Homo sapiens (human)
nucleoplasm	Cellular tumor antigen p53	Homo sapiens (human)
replication fork	Cellular tumor antigen p53	Homo sapiens (human)
nucleolus	Cellular tumor antigen p53	Homo sapiens (human)
cytoplasm	Cellular tumor antigen p53	Homo sapiens (human)
mitochondrion	Cellular tumor antigen p53	Homo sapiens (human)
mitochondrial matrix	Cellular tumor antigen p53	Homo sapiens (human)
endoplasmic reticulum	Cellular tumor antigen p53	Homo sapiens (human)
centrosome	Cellular tumor antigen p53	Homo sapiens (human)
cytosol	Cellular tumor antigen p53	Homo sapiens (human)
nuclear matrix	Cellular tumor antigen p53	Homo sapiens (human)
PML body	Cellular tumor antigen p53	Homo sapiens (human)
transcription repressor complex	Cellular tumor antigen p53	Homo sapiens (human)
site of double-strand break	Cellular tumor antigen p53	Homo sapiens (human)
germ cell nucleus	Cellular tumor antigen p53	Homo sapiens (human)
chromatin	Cellular tumor antigen p53	Homo sapiens (human)
transcription regulator complex	Cellular tumor antigen p53	Homo sapiens (human)
protein-containing complex	Cellular tumor antigen p53	Homo sapiens (human)
glutamatergic synapse	Integrin beta-3	Homo sapiens (human)
nucleus	Integrin beta-3	Homo sapiens (human)
nucleoplasm	Integrin beta-3	Homo sapiens (human)
plasma membrane	Integrin beta-3	Homo sapiens (human)
cell-cell junction	Integrin beta-3	Homo sapiens (human)
focal adhesion	Integrin beta-3	Homo sapiens (human)
external side of plasma membrane	Integrin beta-3	Homo sapiens (human)
cell surface	Integrin beta-3	Homo sapiens (human)
apical plasma membrane	Integrin beta-3	Homo sapiens (human)
platelet alpha granule membrane	Integrin beta-3	Homo sapiens (human)
lamellipodium membrane	Integrin beta-3	Homo sapiens (human)
filopodium membrane	Integrin beta-3	Homo sapiens (human)
microvillus membrane	Integrin beta-3	Homo sapiens (human)
ruffle membrane	Integrin beta-3	Homo sapiens (human)
integrin alphav-beta3 complex	Integrin beta-3	Homo sapiens (human)
melanosome	Integrin beta-3	Homo sapiens (human)
synapse	Integrin beta-3	Homo sapiens (human)
postsynaptic membrane	Integrin beta-3	Homo sapiens (human)
extracellular exosome	Integrin beta-3	Homo sapiens (human)
integrin alphaIIb-beta3 complex	Integrin beta-3	Homo sapiens (human)
glycinergic synapse	Integrin beta-3	Homo sapiens (human)
integrin complex	Integrin beta-3	Homo sapiens (human)
protein-containing complex	Integrin beta-3	Homo sapiens (human)
alphav-beta3 integrin-PKCalpha complex	Integrin beta-3	Homo sapiens (human)
alphav-beta3 integrin-IGF-1-IGF1R complex	Integrin beta-3	Homo sapiens (human)
alphav-beta3 integrin-HMGB1 complex	Integrin beta-3	Homo sapiens (human)
receptor complex	Integrin beta-3	Homo sapiens (human)
alphav-beta3 integrin-vitronectin complex	Integrin beta-3	Homo sapiens (human)
alpha9-beta1 integrin-ADAM8 complex	Integrin beta-3	Homo sapiens (human)
focal adhesion	Integrin beta-3	Homo sapiens (human)
cell surface	Integrin beta-3	Homo sapiens (human)
synapse	Integrin beta-3	Homo sapiens (human)
collagen-containing extracellular matrix	Plasminogen activator inhibitor 1	Homo sapiens (human)
extracellular region	Plasminogen activator inhibitor 1	Homo sapiens (human)
extracellular space	Plasminogen activator inhibitor 1	Homo sapiens (human)
plasma membrane	Plasminogen activator inhibitor 1	Homo sapiens (human)
platelet alpha granule lumen	Plasminogen activator inhibitor 1	Homo sapiens (human)
collagen-containing extracellular matrix	Plasminogen activator inhibitor 1	Homo sapiens (human)
extracellular exosome	Plasminogen activator inhibitor 1	Homo sapiens (human)
serine protease inhibitor complex	Plasminogen activator inhibitor 1	Homo sapiens (human)
peptidase inhibitor complex	Plasminogen activator inhibitor 1	Homo sapiens (human)
extracellular space	Plasminogen activator inhibitor 1	Homo sapiens (human)
cytosol	Carbonic anhydrase 3	Homo sapiens (human)
cytosol	Carbonic anhydrase 3	Homo sapiens (human)
cytoplasm	Carbonic anhydrase 3	Homo sapiens (human)
collagen-containing extracellular matrix	72 kDa type IV collagenase	Homo sapiens (human)
extracellular region	72 kDa type IV collagenase	Homo sapiens (human)
extracellular space	72 kDa type IV collagenase	Homo sapiens (human)
nucleus	72 kDa type IV collagenase	Homo sapiens (human)
mitochondrion	72 kDa type IV collagenase	Homo sapiens (human)
plasma membrane	72 kDa type IV collagenase	Homo sapiens (human)
sarcomere	72 kDa type IV collagenase	Homo sapiens (human)
collagen-containing extracellular matrix	72 kDa type IV collagenase	Homo sapiens (human)
extracellular space	72 kDa type IV collagenase	Homo sapiens (human)
plasma membrane	Integrin alpha-IIb	Homo sapiens (human)
focal adhesion	Integrin alpha-IIb	Homo sapiens (human)
cell surface	Integrin alpha-IIb	Homo sapiens (human)
platelet alpha granule membrane	Integrin alpha-IIb	Homo sapiens (human)
extracellular exosome	Integrin alpha-IIb	Homo sapiens (human)
integrin alphaIIb-beta3 complex	Integrin alpha-IIb	Homo sapiens (human)
blood microparticle	Integrin alpha-IIb	Homo sapiens (human)
integrin complex	Integrin alpha-IIb	Homo sapiens (human)
external side of plasma membrane	Integrin alpha-IIb	Homo sapiens (human)
extracellular region	Matrilysin	Homo sapiens (human)
extracellular matrix	Matrilysin	Homo sapiens (human)
extracellular exosome	Matrilysin	Homo sapiens (human)
extracellular space	Matrilysin	Homo sapiens (human)
extracellular space	Angiotensin-converting enzyme	Homo sapiens (human)
extracellular region	Angiotensin-converting enzyme	Homo sapiens (human)
extracellular space	Angiotensin-converting enzyme	Homo sapiens (human)
lysosome	Angiotensin-converting enzyme	Homo sapiens (human)
endosome	Angiotensin-converting enzyme	Homo sapiens (human)
plasma membrane	Angiotensin-converting enzyme	Homo sapiens (human)
external side of plasma membrane	Angiotensin-converting enzyme	Homo sapiens (human)
basal plasma membrane	Angiotensin-converting enzyme	Homo sapiens (human)
brush border membrane	Angiotensin-converting enzyme	Homo sapiens (human)
extracellular exosome	Angiotensin-converting enzyme	Homo sapiens (human)
sperm midpiece	Angiotensin-converting enzyme	Homo sapiens (human)
plasma membrane	Angiotensin-converting enzyme	Homo sapiens (human)
plasma membrane	L-selectin	Homo sapiens (human)
secretory granule membrane	L-selectin	Homo sapiens (human)
external side of plasma membrane	L-selectin	Homo sapiens (human)
extracellular space	L-selectin	Homo sapiens (human)
extracellular space	P-selectin	Homo sapiens (human)
plasma membrane	P-selectin	Homo sapiens (human)
external side of plasma membrane	P-selectin	Homo sapiens (human)
platelet dense granule membrane	P-selectin	Homo sapiens (human)
platelet alpha granule membrane	P-selectin	Homo sapiens (human)
extracellular space	P-selectin	Homo sapiens (human)
external side of plasma membrane	P-selectin	Homo sapiens (human)
extracellular space	E-selectin	Homo sapiens (human)
plasma membrane	E-selectin	Homo sapiens (human)
caveola	E-selectin	Homo sapiens (human)
clathrin-coated pit	E-selectin	Homo sapiens (human)
cortical cytoskeleton	E-selectin	Homo sapiens (human)
membrane raft	E-selectin	Homo sapiens (human)
perinuclear region of cytoplasm	E-selectin	Homo sapiens (human)
external side of plasma membrane	E-selectin	Homo sapiens (human)
extracellular space	E-selectin	Homo sapiens (human)
endoplasmic reticulum lumen	Prolyl 4-hydroxylase subunit alpha-1	Gallus gallus (chicken)
endoplasmic reticulum	Prolyl 4-hydroxylase subunit alpha-1	Gallus gallus (chicken)
plasma membrane	Glutamate receptor 2	Rattus norvegicus (Norway rat)
basolateral plasma membrane	Carbonic anhydrase 4	Homo sapiens (human)
rough endoplasmic reticulum	Carbonic anhydrase 4	Homo sapiens (human)
endoplasmic reticulum-Golgi intermediate compartment	Carbonic anhydrase 4	Homo sapiens (human)
Golgi apparatus	Carbonic anhydrase 4	Homo sapiens (human)
trans-Golgi network	Carbonic anhydrase 4	Homo sapiens (human)
plasma membrane	Carbonic anhydrase 4	Homo sapiens (human)
external side of plasma membrane	Carbonic anhydrase 4	Homo sapiens (human)
cell surface	Carbonic anhydrase 4	Homo sapiens (human)
membrane	Carbonic anhydrase 4	Homo sapiens (human)
apical plasma membrane	Carbonic anhydrase 4	Homo sapiens (human)
transport vesicle membrane	Carbonic anhydrase 4	Homo sapiens (human)
secretory granule membrane	Carbonic anhydrase 4	Homo sapiens (human)
brush border membrane	Carbonic anhydrase 4	Homo sapiens (human)
perinuclear region of cytoplasm	Carbonic anhydrase 4	Homo sapiens (human)
extracellular exosome	Carbonic anhydrase 4	Homo sapiens (human)
plasma membrane	Carbonic anhydrase 4	Homo sapiens (human)
extracellular region	Carbonic anhydrase 6	Homo sapiens (human)
extracellular space	Carbonic anhydrase 6	Homo sapiens (human)
cytosol	Carbonic anhydrase 6	Homo sapiens (human)
extracellular exosome	Carbonic anhydrase 6	Homo sapiens (human)
extracellular space	Carbonic anhydrase 6	Homo sapiens (human)
extracellular region	Dipeptidyl peptidase 4	Homo sapiens (human)
lysosomal membrane	Dipeptidyl peptidase 4	Homo sapiens (human)
plasma membrane	Dipeptidyl peptidase 4	Homo sapiens (human)
focal adhesion	Dipeptidyl peptidase 4	Homo sapiens (human)
cell surface	Dipeptidyl peptidase 4	Homo sapiens (human)
membrane	Dipeptidyl peptidase 4	Homo sapiens (human)
apical plasma membrane	Dipeptidyl peptidase 4	Homo sapiens (human)
lamellipodium	Dipeptidyl peptidase 4	Homo sapiens (human)
endocytic vesicle	Dipeptidyl peptidase 4	Homo sapiens (human)
lamellipodium membrane	Dipeptidyl peptidase 4	Homo sapiens (human)
membrane raft	Dipeptidyl peptidase 4	Homo sapiens (human)
intercellular canaliculus	Dipeptidyl peptidase 4	Homo sapiens (human)
extracellular exosome	Dipeptidyl peptidase 4	Homo sapiens (human)
plasma membrane	Dipeptidyl peptidase 4	Homo sapiens (human)
nucleus	Proteasome subunit beta type-5	Homo sapiens (human)
cytoplasm	Proteasome subunit beta type-5	Homo sapiens (human)
proteasome complex	Proteasome subunit beta type-5	Homo sapiens (human)
nucleus	Proteasome subunit beta type-5	Homo sapiens (human)
nucleoplasm	Proteasome subunit beta type-5	Homo sapiens (human)
centrosome	Proteasome subunit beta type-5	Homo sapiens (human)
cytosol	Proteasome subunit beta type-5	Homo sapiens (human)
extracellular exosome	Proteasome subunit beta type-5	Homo sapiens (human)
proteasome core complex	Proteasome subunit beta type-5	Homo sapiens (human)
proteasome core complex, beta-subunit complex	Proteasome subunit beta type-5	Homo sapiens (human)
cytosol	Proteasome subunit beta type-5	Homo sapiens (human)
Golgi membrane	Adenosine receptor A2a	Rattus norvegicus (Norway rat)
mitochondrial matrix	Carbonic anhydrase 5A, mitochondrial	Homo sapiens (human)
mitochondrion	Carbonic anhydrase 5A, mitochondrial	Homo sapiens (human)
cytoplasm	Carbonic anhydrase 5A, mitochondrial	Homo sapiens (human)
mitochondrion	Carbonic anhydrase 5A, mitochondrial	Homo sapiens (human)
platelet alpha granule membrane	Alpha-synuclein	Homo sapiens (human)
extracellular region	Alpha-synuclein	Homo sapiens (human)
extracellular space	Alpha-synuclein	Homo sapiens (human)
nucleus	Alpha-synuclein	Homo sapiens (human)
cytoplasm	Alpha-synuclein	Homo sapiens (human)
mitochondrion	Alpha-synuclein	Homo sapiens (human)
lysosome	Alpha-synuclein	Homo sapiens (human)
cytosol	Alpha-synuclein	Homo sapiens (human)
plasma membrane	Alpha-synuclein	Homo sapiens (human)
cell cortex	Alpha-synuclein	Homo sapiens (human)
actin cytoskeleton	Alpha-synuclein	Homo sapiens (human)
membrane	Alpha-synuclein	Homo sapiens (human)
inclusion body	Alpha-synuclein	Homo sapiens (human)
axon	Alpha-synuclein	Homo sapiens (human)
growth cone	Alpha-synuclein	Homo sapiens (human)
synaptic vesicle membrane	Alpha-synuclein	Homo sapiens (human)
perinuclear region of cytoplasm	Alpha-synuclein	Homo sapiens (human)
postsynapse	Alpha-synuclein	Homo sapiens (human)
supramolecular fiber	Alpha-synuclein	Homo sapiens (human)
protein-containing complex	Alpha-synuclein	Homo sapiens (human)
cytoplasm	Alpha-synuclein	Homo sapiens (human)
axon terminus	Alpha-synuclein	Homo sapiens (human)
neuronal cell body	Alpha-synuclein	Homo sapiens (human)
cytosol	Carbonic anhydrase 7	Homo sapiens (human)
cytoplasm	Carbonic anhydrase 7	Homo sapiens (human)
Golgi membrane	4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT6	Homo sapiens (human)
extracellular region	4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT6	Homo sapiens (human)
Golgi apparatus	4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT6	Homo sapiens (human)
Golgi cisterna membrane	4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT6	Homo sapiens (human)
extracellular exosome	4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT6	Homo sapiens (human)
methylosome	4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT6	Homo sapiens (human)
extracellular region	Anthrax toxin receptor 2	Homo sapiens (human)
endoplasmic reticulum membrane	Anthrax toxin receptor 2	Homo sapiens (human)
plasma membrane	Anthrax toxin receptor 2	Homo sapiens (human)
endosome membrane	Anthrax toxin receptor 2	Homo sapiens (human)
plasma membrane	Anthrax toxin receptor 2	Homo sapiens (human)
cell surface	Anthrax toxin receptor 2	Homo sapiens (human)
cell-cell junction	Disintegrin and metalloproteinase domain-containing protein 17	Homo sapiens (human)
focal adhesion	Disintegrin and metalloproteinase domain-containing protein 17	Homo sapiens (human)
ruffle membrane	Disintegrin and metalloproteinase domain-containing protein 17	Homo sapiens (human)
Golgi membrane	Disintegrin and metalloproteinase domain-containing protein 17	Homo sapiens (human)
cytoplasm	Disintegrin and metalloproteinase domain-containing protein 17	Homo sapiens (human)
endoplasmic reticulum lumen	Disintegrin and metalloproteinase domain-containing protein 17	Homo sapiens (human)
cytosol	Disintegrin and metalloproteinase domain-containing protein 17	Homo sapiens (human)
plasma membrane	Disintegrin and metalloproteinase domain-containing protein 17	Homo sapiens (human)
cell surface	Disintegrin and metalloproteinase domain-containing protein 17	Homo sapiens (human)
actin cytoskeleton	Disintegrin and metalloproteinase domain-containing protein 17	Homo sapiens (human)
membrane	Disintegrin and metalloproteinase domain-containing protein 17	Homo sapiens (human)
apical plasma membrane	Disintegrin and metalloproteinase domain-containing protein 17	Homo sapiens (human)
membrane raft	Disintegrin and metalloproteinase domain-containing protein 17	Homo sapiens (human)
plasma membrane	Disintegrin and metalloproteinase domain-containing protein 17	Homo sapiens (human)
extracellular space	Lactoperoxidase	Bos taurus (cattle)
cytoplasm	Lactoperoxidase	Bos taurus (cattle)
Golgi apparatus	Polypeptide N-acetylgalactosaminyltransferase 2	Homo sapiens (human)
Golgi membrane	Polypeptide N-acetylgalactosaminyltransferase 2	Homo sapiens (human)
extracellular region	Polypeptide N-acetylgalactosaminyltransferase 2	Homo sapiens (human)
endoplasmic reticulum membrane	Polypeptide N-acetylgalactosaminyltransferase 2	Homo sapiens (human)
Golgi apparatus	Polypeptide N-acetylgalactosaminyltransferase 2	Homo sapiens (human)
Golgi stack	Polypeptide N-acetylgalactosaminyltransferase 2	Homo sapiens (human)
membrane	Polypeptide N-acetylgalactosaminyltransferase 2	Homo sapiens (human)
Golgi cisterna membrane	Polypeptide N-acetylgalactosaminyltransferase 2	Homo sapiens (human)
perinuclear region of cytoplasm	Polypeptide N-acetylgalactosaminyltransferase 2	Homo sapiens (human)
Golgi apparatus	Polypeptide N-acetylgalactosaminyltransferase 2	Homo sapiens (human)
Golgi membrane	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
Golgi apparatus	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
trans-Golgi network	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
membrane	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
Golgi cisterna membrane	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
Golgi membrane	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)
membrane	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)
trans-Golgi network membrane	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)
extracellular exosome	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)
Golgi medial cisterna membrane	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)
Golgi trans cisterna membrane	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)
membrane	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)
nucleolus	Carbonic anhydrase 9	Homo sapiens (human)
plasma membrane	Carbonic anhydrase 9	Homo sapiens (human)
membrane	Carbonic anhydrase 9	Homo sapiens (human)
basolateral plasma membrane	Carbonic anhydrase 9	Homo sapiens (human)
microvillus membrane	Carbonic anhydrase 9	Homo sapiens (human)
plasma membrane	Carbonic anhydrase 9	Homo sapiens (human)
plasma membrane	Carbonic anhydrase 14	Homo sapiens (human)
membrane	Carbonic anhydrase 14	Homo sapiens (human)
basolateral plasma membrane	Carbonic anhydrase 14	Homo sapiens (human)
apical plasma membrane	Carbonic anhydrase 14	Homo sapiens (human)
plasma membrane	Carbonic anhydrase 14	Homo sapiens (human)
mitochondrion	Carbonic anhydrase 5B, mitochondrial	Homo sapiens (human)
mitochondrial matrix	Carbonic anhydrase 5B, mitochondrial	Homo sapiens (human)
mitochondrion	Carbonic anhydrase 5B, mitochondrial	Homo sapiens (human)
cytoplasm	Carbonic anhydrase 5B, mitochondrial	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (592)

Assay ID	Title	Year	Journal	Article
AID1347351	U-118MG Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347393	qHTS for inhibitors of ER calcium dysfunction: SERCaMP assay screened against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347363	Firefly luciferase counterscreen qHTS: Assay Interference Panel against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347387	Cytotoxicity qHTS for assessment of Hepg2 cells membrane integrity screened against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347345	OV-KATE Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347400	Viability qHTS for inhibitors of the SERCaMP assay screened against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347349	Panc-1005 Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347402	qHTS for inhibitors of Rabies Virus screened against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347376	10-beta competent E. coli microbial cell viability qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347381	Inflammasome Signaling qHTS Counterscreen: IL-1-beta AlphaLISA counterscreen against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347357	HEK293 18hr Apoptosis Induction qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347378	qHTS for H2AX Agonists against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347352	COV-362 Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347362	Diaphorse counterscreen qHTS: Assay Interference Panel against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347391	qHTS for activators of Nrf2/ARE signaling pathway screened against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347361	HEK293 12hr Apoptosis Induction qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347377	DH5-alpha competent E. coli microbial cell viability qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347394	Vero-766 cells viability qHTS against the NCATS CANVASS Library: Counterscreen for Zika virus inhibition assay	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347370	qHTS for ATAD5 Antagonist screened against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347160	Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors	2020	Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49	Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347358	HPAF-II 12hr Apoptosis Induction qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347369	MCF7 Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347347	UWB1.289 Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347373	qHTS for Constitutive Androstane Receptor (CAR) Agonist screened against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347365	SDT Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347368	G06 Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347353	A2780 Cisplatin Sensitive Ovarian Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347356	HPAF-II 24hr Apoptosis Induction qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347359	HEK293 24hr Apoptosis Induction qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347348	OV-SAHO Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347396	qHTS for inhibitors of Wild type Zika virus screened against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347367	qHTS for ATAD5 Agonist screened against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347389	qHTS assay for small molecule disruptors of mitochondrial membrane potential screened against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347355	HEK-293 Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347375	qHTS for Hypoxia signaling pathway (HIF-1) agonists against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347390	Secretion counterscreen for inhibitors of the SERCaMP assay screened against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347346	HPAF-II Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347350	SW1088 Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347379	qHTS for Inflammasome Signaling Inhibitors: IL-1-beta AlphaLISA screen against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347364	KB-8-5-11 Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347366	KB-3-1 Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347372	qHTS for Constitutive Androstane Receptor (CAR) Antagonist screened against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347354	UWB1.289-WTBRCA1 Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347371	J3T Cancer Cell Toxicity qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347392	qHTS for activators of dead-cell proteases activity screened against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347360	HPAF-II 18hr Apoptosis Induction qHTS against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347388	qHTS for Activators of p53 Stress Response Pathway screened against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347380	qHTS for Antimalaria activity screened against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347401	Redox Reaction Profiling qHTS: Assay Interference Panel against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1347374	qHTS for Hypoxia signaling pathway (HIF-1) antagonists against the NCATS CANVASS Library	2018	ACS central science, Dec-26, Volume: 4, Issue:12	Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.
AID1311760	Antiinflammatory activity against LPS-stimulated mouse RAW264.7 cells assessed as TNFalpha levels at 5 umol/L by ELISA (Rvb = 183.21 +/- 5.36 pg/mL)	2016	Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15	Anti-inflammatory polyphenol constituents derived from Cissus pteroclada Hayata.
AID1197620	Antiviral activity against HIV1 3B infected in human CEM cells assessed as reduction in virus-induced cytopathicity after 4 to 5 days by microscopy based syncytium cell formation assay	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID1082350	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 0.25% under dark conditions measured 24 hr post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID711604	Increase of frequency of pharyngeal pumping in Caenorhabditis elegans at 300 uM on 9th day of adulthood	2011	Journal of natural products, Aug-26, Volume: 74, Issue:8	Diversity of polyphenol action in Caenorhabditis elegans: between toxicity and longevity.
AID462279	Inhibition of human CA12 by stopped-flow CO2 hydration assay	2010	Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6	Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids.
AID381926	Cytotoxicity against african green monkey VERO cells	2008	Bioorganic & medicinal chemistry, Apr-01, Volume: 16, Issue:7	Ester derivatives of gallic acid with potential toxicity toward L1210 leukemia cells.
AID380374	DPPH radical scavenging activity at 20 uM after 30 mins by spectrophotometric assay	2000	Journal of natural products, Jun, Volume: 63, Issue:6	Galloylglucosides from berries of Pimenta dioica.
AID1311780	Antiinflammatory activity against LPS-stimulated mouse RAW264.7 cells assessed as COX2 levels at 25 umol/L by ELISA (Rvb = 159.64 +/- 13.56 pg/mL)	2016	Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15	Anti-inflammatory polyphenol constituents derived from Cissus pteroclada Hayata.
AID377795	Cytotoxicity against dog RBC	2005	Journal of natural products, Apr, Volume: 68, Issue:4	Anti-babesial and anti-plasmodial compounds from Phyllanthus niruri.
AID417964	Antimicrobial activity against Aspergillus flavus after 48 hrs by broth microdilution technique	2009	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 19, Issue:6	Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi.
AID1491528	Cytoprotective activity against H2O2-induced apoptosis in rat PC12 cells assessed as late apoptotic cells at 100 uM preincubated for 0.5 hrs followed by H2O2 addition measured after 2 hrs by Annexin V-FITC/propidium iodide staining based flow cytometry (R	2017	European journal of medicinal chemistry, Sep-29, Volume: 138	Synthesis and anti-oxidant activity evaluation of (±)-Anastatins A, B and their analogs.
AID732058	Cytotoxicity against human PLC/PRF/5 cells	2013	European journal of medicinal chemistry, Feb, Volume: 60	Alkyl esters of gallic acid as anticancer agents: a review.
AID381922	Decrease in mitochondrial glutathione level in mouse L1210 cells	2008	Bioorganic & medicinal chemistry, Apr-01, Volume: 16, Issue:7	Ester derivatives of gallic acid with potential toxicity toward L1210 leukemia cells.
AID1311773	Antiinflammatory activity against LPS-stimulated mouse RAW264.7 cells assessed as iNOS levels at 25 umol/L by ELISA (Rvb = 31.63 +/- 3.26 U/mL)	2016	Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15	Anti-inflammatory polyphenol constituents derived from Cissus pteroclada Hayata.
AID83435	Inhibition of polymerization in wild type HIV-1 RT with poly rC/dG12-18 template primer and [3H]dGTP	2001	Bioorganic & medicinal chemistry letters, Oct-22, Volume: 11, Issue:20	Simplified catechin-gallate inhibitors of HIV-1 reverse transcriptase.
AID1187066	Inhibition of insulin fibril formation (unknown origin) assessed as turbidity at 1:5 insulin to compound ratio at pH2 up to 12 hrs by UV/vis spectrometry	2014	European journal of medicinal chemistry, Oct-06, Volume: 85	Gallic acid, one of the components in many plant tissues, is a potential inhibitor for insulin amyloid fibril formation.
AID1311775	Inhibition of NFkappaB signaling pathway in LPS-stimulated mouse RAW264.7 cells assessed as protein levels at 5 umol/L by ELISA (Rvb = 1.23 +/- 0.06 pg/mL)	2016	Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15	Anti-inflammatory polyphenol constituents derived from Cissus pteroclada Hayata.
AID1630424	Increase in PARP level in human NCI-H460 cells harboring wild-type EGFR at 30 and 60 uM by immunoblotting analysis	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID1083160	Antifungal activity against Neofusicoccum luteum CBS110299 assessed as growth inhibition measured after 1 to 10 days	2012	Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48	Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID1055132	Effect on RCM-kappa-casein-induced cytotoxicity against rat PC12 cells assessed as increase in cell viability at 1:2 protein to compound molar ratio after 48 hrs by MTT assay relative to control	2013	Bioorganic & medicinal chemistry letters, Dec-01, Volume: 23, Issue:23	Gallic acid is the major component of grape seed extract that inhibits amyloid fibril formation.
AID1494600	Anticomplement activity in rabbit erythrocytes assessed as concentration required for 50% hemolytic inhibition by alternative pathway pretreated for 10 mins with normal human serum followed by erythrocyte addition measured after 30 mins by spectrophotomet	2018	Bioorganic & medicinal chemistry letters, 05-15, Volume: 28, Issue:9	Anticomplement compounds from Polygonum chinense.
AID1491521	Cytoprotective activity against H2O2-induced oxidative damage in rat PC12 cells assessed as reduction in morphological changes by measuring membrane blebbing at 10 to 100 uM preincubated for 0.5 hrs followed by H2O2 addition measured after 2 hrs	2017	European journal of medicinal chemistry, Sep-29, Volume: 138	Synthesis and anti-oxidant activity evaluation of (±)-Anastatins A, B and their analogs.
AID1630441	Induction of EGFR turnover in human NCI-H1975 cells harboring EGFR-mutant at 60 uM measured after 24 hrs in presence of proteosome inhibitor bortezomib by immunoblotting analysis	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID1128677	Cytotoxicity against human CCRF-CEM cells after 48 hrs by neutral red assay	2014	Journal of medicinal chemistry, Mar-27, Volume: 57, Issue:6	Antiproliferative and uncoupling effects of delocalized, lipophilic, cationic gallic acid derivatives on cancer cell lines. Validation in vivo in singenic mice.
AID1399448	Induction of apoptosis in human A549 cells assessed as early apoptotic cells at 2.5 uM after 48 hrs by Annexin-V-FITC/propidium iodide staining based flow cytometry (Rvb = 15.2%)	2018	Bioorganic & medicinal chemistry, 08-15, Volume: 26, Issue:15	Anti-angiogenic and anticancer effects of baicalein derivatives based on transgenic zebrafish model.
AID1591479	Antioxidant activity assessed as DPPH radical scavenging activity at 10 uM preincubated for 5 mins followed by DPPH addition and measured after 30 mins by ultraviolet spectrophotometric analysis relative to control	2019	Bioorganic & medicinal chemistry, 07-15, Volume: 27, Issue:14	Naphthalene-triazolopyrimidine hybrid compounds as potential multifunctional anti-Alzheimer's agents.
AID1310999	Cytotoxicity against BAECs assessed as decrease in total intracellular LDH content at 15 mM measured after 3 hrs by LDH assay relative to vehicle control	2016	European journal of medicinal chemistry, Aug-25, Volume: 119	On the vasoprotective mechanisms underlying novel β-phosphorylated nitrones: Focus on free radical characterization, scavenging and NO-donation in a biological model of oxidative stress.
AID711617	Increase of lifespan of L4 larvae of Caenorhabditis elegans at 300 uM in presence of heat killed bacteria	2011	Journal of natural products, Aug-26, Volume: 74, Issue:8	Diversity of polyphenol action in Caenorhabditis elegans: between toxicity and longevity.
AID1129834	Inhibition of Influenza A virus (A/RI/5+/1957(H2N2)) recombinant neuraminidase using MUNANA as substrate after 30 mins	2014	Bioorganic & medicinal chemistry, Apr-01, Volume: 22, Issue:7	Benzophenone C-glucosides and gallotannins from mango tree stem bark with broad-spectrum anti-viral activity.
AID1363739	Inhibition of Influenza A (A/California/04/2009) (H1N1) clinical isolate N-terminal truncated PA endonuclease using 5'-FAM/3-TAMRA quencer labeled 17-mer ssDNA-oligo as substrate measured over 45 mins by FRET assay	2018	Journal of medicinal chemistry, 11-21, Volume: 61, Issue:22	Structure-Activity Relationships in Metal-Binding Pharmacophores for Influenza Endonuclease.
AID1630448	Increase in cleaved caspase3 level in human gefitinib-resistant PC9 cells harboring EGFR T790M mutant at 30 and 60 uM by immunoblotting analysis	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID638443	Antioxidant activity assessed as DPPH free radical scavenging activity after 30 mins	2012	Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1	Maplexins, new α-glucosidase inhibitors from red maple (Acer rubrum) stems.
AID381928	Induction of apoptosis in human CEM cells assessed as internucleosomal breakdown of DNA chromatin at 30 uM	2008	Bioorganic & medicinal chemistry, Apr-01, Volume: 16, Issue:7	Ester derivatives of gallic acid with potential toxicity toward L1210 leukemia cells.
AID1204902	Antioxidant activity assessed as DPPH free radical scavenging activity measured as decoloration of a MeOH solution after 10 mins by spectrophotometry	2015	Journal of natural products, Feb-27, Volume: 78, Issue:2	Iridoid glycosides from Barleria lupulina.
AID1082344	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 1% under light conditions measured 5 to 60 min post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID607497	Inhibition of Dicentrarchus labrax CA using 4-nitrophenylacetate substrate by esterase assay	2011	Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14	In vitro inhibition of α-carbonic anhydrase isozymes by some phenolic compounds.
AID736487	Antioxidant activity assessed as inhibition of DPPH radical formation measured every min for 45 mins by spectrophotometric analysis	2013	European journal of medicinal chemistry, Apr, Volume: 62	Exploring nature profits: development of novel and potent lipophilic antioxidants based on galloyl-cinnamic hybrids.
AID377830	Antioxidant activity assessed as DPPH radical scavenging activity after 30 mins	2005	Journal of natural products, Apr, Volume: 68, Issue:4	Chemical constituents of the fruits of Morinda citrifolia (Noni) and their antioxidant activity.
AID1491517	Antioxidant activity assessed as vitamin-c equivalents of ferric ion reducing activity by measuring Fe2+ levels using Fe3+-TPTZ by FRAP assay	2017	European journal of medicinal chemistry, Sep-29, Volume: 138	Synthesis and anti-oxidant activity evaluation of (±)-Anastatins A, B and their analogs.
AID1187074	Inhibition of insulin fibril formation (unknown origin) assessed as secondary structural changes at 1:5 insulin to compound ratio at pH2 up to 12 hrs by FT-IR technique	2014	European journal of medicinal chemistry, Oct-06, Volume: 85	Gallic acid, one of the components in many plant tissues, is a potential inhibitor for insulin amyloid fibril formation.
AID417969	Antimicrobial activity against Trichophyton mentagrophytes after 48 hrs by broth microdilution technique	2009	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 19, Issue:6	Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi.
AID711624	Increase of lifespan of L4 larvae of Caenorhabditis elegans at 35 degC after 8 hrs	2011	Journal of natural products, Aug-26, Volume: 74, Issue:8	Diversity of polyphenol action in Caenorhabditis elegans: between toxicity and longevity.
AID1630426	Effect on ROS level in human NCI-H1650 cells harboring EGFR-mutant at 60 uM	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID1197622	Cytotoxicity against human CEM cells assessed as inhibition of cell proliferation	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID382837	DPPH radical scavenging activity after 180 mins	2008	Journal of natural products, May, Volume: 71, Issue:5	Phenolic glycosides from berries of Pimenta dioica.
AID1105379	Antioxidant activity assessed as DPPH free radical scavenging activity at 0.1 ug/mL after 20 min by UV-Vis spectrophotometric analysis	2013	European journal of medicinal chemistry, Jan, Volume: 59	Microwave synthesis, characterization and bio-efficacy evaluation of novel chalcone based 6-carbethoxy-2-cyclohexen-1-one and 2H-indazol-3-ol derivatives.
AID475261	Antioxidant activity assessed as DPPH free radical scavenging activity at 1 uM after 4 mins by spectrophotometry	2010	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 20, Issue:7	Synthesis and biological evaluation of nitrogen-containing benzophenone analogues as TNF-alpha and IL-6 inhibitors with antioxidant activity.
AID536046	Antioxidant activity against ABTS radical assessed as Trolox equivalent	2010	Bioorganic & medicinal chemistry, Nov-15, Volume: 18, Issue:22	Synthesis and antioxidant properties of pulvinic acids analogues.
AID1588069	Binding affinity of human recombinant FLAG-tagged ppGalNAcT2 expressed in HEK293 cells assessed as dissociation rate by SPR analysis	2019	Bioorganic & medicinal chemistry, 08-01, Volume: 27, Issue:15	Inhibition of polypeptide N-acetyl-α-galactosaminyltransferases is an underlying mechanism of dietary polyphenols preventing colorectal tumorigenesis.
AID1630413	Induction of apoptosis in human NCI-H1975 harboring EGFR-mutant cells assessed as cell death measured after 24 hrs by Annexin-V/PI staining based analysis	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID1310992	Antioxidant activity assessed as inhibition of allopurinol-xanthine oxidase system-mediated superoxide formation measured over 7 mins by lucigenin-based chemiluminescence analysis	2016	European journal of medicinal chemistry, Aug-25, Volume: 119	On the vasoprotective mechanisms underlying novel β-phosphorylated nitrones: Focus on free radical characterization, scavenging and NO-donation in a biological model of oxidative stress.
AID437510	Inhibition of MET kinase	2009	Journal of medicinal chemistry, Nov-12, Volume: 52, Issue:21	Tea catechins inhibit hepatocyte growth factor receptor (MET kinase) activity in human colon cancer cells: kinetic and molecular docking studies.
AID380372	DPPH radical scavenging activity at 80 uM after 30 mins by spectrophotometric assay	2000	Journal of natural products, Jun, Volume: 63, Issue:6	Galloylglucosides from berries of Pimenta dioica.
AID1082340	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 5% under dark conditions measured 5 to 60 min post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID1082357	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 0.125% under light conditions measured 24 hr post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID1630449	Increase in cleaved caspase3 level in human erlotinib-resistant PC9 cells harboring EGFR T790M mutant at 30 and 60 uM by immunoblotting analysis	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID1197646	Antiviral activity against punta toro virus	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID315606	Growth inhibition of human BGC823 cells at 5 uM after 72 hrs by MTT assay relative to control	2008	Bioorganic & medicinal chemistry, Feb-01, Volume: 16, Issue:3	Studies on the chemical constituents and anticancer activity of Saxifraga stolonifera (L) Meeb.
AID1311762	Antiinflammatory activity against LPS-stimulated mouse RAW264.7 cells assessed as TNFalpha levels at 50 umol/L by ELISA (Rvb = 183.21 +/- 5.36 pg/mL)	2016	Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15	Anti-inflammatory polyphenol constituents derived from Cissus pteroclada Hayata.
AID1664683	Inhibition of alpha-synuclein aggregation (unknown origin) at 30 uM incubated for 3 days by thioflavin T based fluorescence assay relative to control	2020	Bioorganic & medicinal chemistry, 08-01, Volume: 28, Issue:15	Amide derivatives of Gallic acid: Design, synthesis and evaluation of inhibitory activities against in vitro α-synuclein aggregation.
AID1128678	Cytotoxicity against mouse MM3MG cells after 48 hrs by neutral red assay	2014	Journal of medicinal chemistry, Mar-27, Volume: 57, Issue:6	Antiproliferative and uncoupling effects of delocalized, lipophilic, cationic gallic acid derivatives on cancer cell lines. Validation in vivo in singenic mice.
AID732038	Antimigratory activity against human U87 cells at 40 ug/ml after 8 hrs by wound closure assay	2013	European journal of medicinal chemistry, Feb, Volume: 60	Alkyl esters of gallic acid as anticancer agents: a review.
AID1311766	Antiinflammatory activity against LPS-stimulated mouse RAW264.7 cells assessed as PGE2 levels at 5 umol/L by ELISA (Rvb = 33.2 +/- 2.33 pg/mL)	2016	Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15	Anti-inflammatory polyphenol constituents derived from Cissus pteroclada Hayata.
AID462277	Inhibition of human CA7 by stopped-flow CO2 hydration assay	2010	Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6	Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids.
AID1630436	Inhibition of EGFR-mediated ERK phosphorylation in human A549 cells harboring wild-type EGFR at 30 and 60 uM measured after 24 hrs by immunoblotting analysis	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID397831	Antioxidant activity assessed as DPPH radical scavenging activity after 20 mins by UV-visible spectrophotometry	2002	Journal of natural products, Dec, Volume: 65, Issue:12	An extract of Tagetes lucida and its phenolic constituents as antioxidants.
AID501210	Cytotoxicity against african green monkey Vero cells after 3 days by MTT assay	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	Phloroglucinol glycosides from the fresh fruits of Eucalyptus maideni.
AID132501	Inhibitory activity against nitric oxide production in LPS-activated mouse peritoneal macrophages	2000	Bioorganic & medicinal chemistry letters, Feb-21, Volume: 10, Issue:4	Effects of stilbene constituents from rhubarb on nitric oxide production in lipopolysaccharide-activated macrophages.
AID1630421	Increase in PARP level in human NCI-H1975 cells harboring EGFR-mutant at 30 and 60 uM by immunoblotting analysis	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID397160	Antioxidant activity against AAPH-induced lipid peroxidation in human plasma LDL at 0.01 to 0.1 umol/L preincubated for 1 hr before AAPH challenge	2001	Journal of natural products, Apr, Volume: 64, Issue:4	Specific antioxidant activity of caffeoyl derivatives and other natural phenolic compounds: LDL protection against oxidation and decrease in the proinflammatory lysophosphatidylcholine production.
AID642415	Estrogenic activity at ERalpha in human MVLN cells at 20 ug/mL after 24 hrs by luciferase reporter gene assay relative to E2	2012	Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1	Discovery of estrogen receptor α modulators from natural compounds in Si-Wu-Tang series decoctions using estrogen-responsive MCF-7 breast cancer cells.
AID732053	Cytotoxicity against mouse WEHI231 cells	2013	European journal of medicinal chemistry, Feb, Volume: 60	Alkyl esters of gallic acid as anticancer agents: a review.
AID1187068	Inhibition of insulin fibril formation (unknown origin) assessed as turbidity at 1:50 insulin to compound ratio at pH2 up to 12 hrs by UV/vis spectrometry	2014	European journal of medicinal chemistry, Oct-06, Volume: 85	Gallic acid, one of the components in many plant tissues, is a potential inhibitor for insulin amyloid fibril formation.
AID475264	Antioxidant activity assessed as DPPH free radical scavenging activity at 1 uM after 10 mins by spectrophotometry	2010	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 20, Issue:7	Synthesis and biological evaluation of nitrogen-containing benzophenone analogues as TNF-alpha and IL-6 inhibitors with antioxidant activity.
AID1395903	Inhibition of DPP4 (unknown origin) using Gly-Pro-AMC as substrate preincubated for 4 secs followed by substrate addition and measured after 30 mins by luminescence assay	2018	European journal of medicinal chemistry, May-10, Volume: 151	Recent progress of the development of dipeptidyl peptidase-4 inhibitors for the treatment of type 2 diabetes mellitus.
AID1891162	Inhibition of alpha-glycosidase (unknown origin) using pre-mix of compound and maltose substrate for 10 mins and then followed by enzyme addition and further incubated for 10 mins by microplate reader analysis	2022	Bioorganic & medicinal chemistry letters, 06-01, Volume: 65	Polyphenolic compounds: Synthesis, assessment of antimicrobial effect and enzymes inhibition against important medicinal enzymes with computational details.
AID1630445	Induction of apoptosis in human erlotinib-resistant PC9 cells harboring EGFR T790M mutant assessed as cell death at 30 and 60 uM measured after 24 hrs by Annexin-V/PI staining based analysis	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID380094	Antioxidant activity assessed as DPPH free radical scavenging activity	2006	Journal of natural products, Mar, Volume: 69, Issue:3	Polyphenolic constituents of Actaea racemosa.
AID1126662	Antioxidant activity assessed as DPPH radical scavenging activity by spectrophotometry	2014	European journal of medicinal chemistry, May-06, Volume: 78	One-pot synthesis and radical scavenging activity of novel polyhydroxylated 3-arylcoumarins.
AID1064675	Antioxidant activity of the compound assessed as inhibition of ABTS radicals at 9 uM after 20 mins by spectrophotometric analysis	2014	Bioorganic & medicinal chemistry, Feb-01, Volume: 22, Issue:3	Synthesis, modelling and biological characterization of 3-substituted-1H-indoles as ligands of GluN2B-containing N-methyl-d-aspartate receptors.
AID401338	Antioxidant activity assessed by singlet oxygen scavenging assay	1996	Journal of natural products, Feb, Volume: 59, Issue:2	Natural polyphenols (vegetable tannins) as drugs: possible modes of action.
AID1105375	Antioxidant activity assessed as DPPH free radical scavenging activity at 0.6 ug/mL after 20 min by UV-Vis spectrophotometric analysis	2013	European journal of medicinal chemistry, Jan, Volume: 59	Microwave synthesis, characterization and bio-efficacy evaluation of novel chalcone based 6-carbethoxy-2-cyclohexen-1-one and 2H-indazol-3-ol derivatives.
AID311581	Antioxidant activity assessed as superoxide anion radical scavenging activity	2007	Journal of natural products, Oct, Volume: 70, Issue:10	Structures and radical-scavenging activities of phenolic constituents from the bark of Picea jezoensis var. jezoensis.
AID378879	Antioxidant activity in human HL60 cells assessed as reduction of cytochrome-c release	2000	Journal of natural products, Jan, Volume: 63, Issue:1	Acylated flavonol glycosides from the flower of Inula britannica.
AID1337771	Cytoprotective activity against H2O2-induced oxidative stress in rat PC12 cells assessed as early apoptotic cells at 10 uM pretreated for 0.5 hrs followed by H2O2 challenge measured after 2 hrs by Annexin-V-FITC/propidium iodide staining based flow cytome	2017	European journal of medicinal chemistry, Jan-05, Volume: 125	Synthesis and antioxidant evaluation of desmethylxanthohumol analogs and their dimers.
AID732036	Antimigratory activity against human U251 cells at 40 ug/ml after 8 hrs by wound closure assay	2013	European journal of medicinal chemistry, Feb, Volume: 60	Alkyl esters of gallic acid as anticancer agents: a review.
AID400987	Inhibition of AMV reverse transcriptase activity assessed as incorporation of dTMP in poly(rA)-oligo(dT) at 100 uM
AID1082349	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 0.125% under dark conditions measured 24 hr post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID732041	Inhibition of ADAM17 alpha-secretase activity in human UI87 cells using amyloid beta precursor protein as substrate at 30 ug/ml after 24 hrs by fluorimetric analysis	2013	European journal of medicinal chemistry, Feb, Volume: 60	Alkyl esters of gallic acid as anticancer agents: a review.
AID417960	Antifungal activity against Candida tropicalis after 48 hrs by broth microdilution technique	2009	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 19, Issue:6	Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi.
AID1082343	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 0.5% under light conditions measured 5 to 60 min post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID1491520	Cytoprotective activity against H2O2-induced oxidative damage in rat PC12 cells assessed as reduction in morphological changes by measuring cell shrinkage at 10 to 100 uM preincubated for 0.5 hrs followed by H2O2 addition measured after 2 hrs	2017	European journal of medicinal chemistry, Sep-29, Volume: 138	Synthesis and anti-oxidant activity evaluation of (±)-Anastatins A, B and their analogs.
AID732044	Cytotoxicity against rat epithelial cells	2013	European journal of medicinal chemistry, Feb, Volume: 60	Alkyl esters of gallic acid as anticancer agents: a review.
AID462280	Inhibition of mouse CA13 by stopped-flow CO2 hydration assay	2010	Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6	Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids.
AID711595	Increase of lifespan of Caenorhabditis elegans assessed as ascorbic acid equivalent of water soluble antioxidant metabolites at 300 uM by photochemiluminescence assay	2011	Journal of natural products, Aug-26, Volume: 74, Issue:8	Diversity of polyphenol action in Caenorhabditis elegans: between toxicity and longevity.
AID1588068	Binding affinity of human recombinant FLAG-tagged ppGalNAcT2 expressed in HEK293 cells assessed as association rate by SPR analysis	2019	Bioorganic & medicinal chemistry, 08-01, Volume: 27, Issue:15	Inhibition of polypeptide N-acetyl-α-galactosaminyltransferases is an underlying mechanism of dietary polyphenols preventing colorectal tumorigenesis.
AID400984	Inhibition of AMV reverse transcriptase activity assessed as incorporation of dTMP in poly(rA)-oligo(dT) at 0.1 uM
AID1630440	Effect on EGFR mRNA levels in human NCI-H1975 cells harboring EGFR-mutant at 30 uM by quantitative RT-PCR method	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID1191657	Antioxidant activity assessed as DMPD scavenging activity after 15 mins by spectrophotometry	2015	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 25, Issue:5	Schiff's bases of quinazolinone derivatives: Synthesis and SAR studies of a novel series of potential anti-inflammatory and antioxidants.
AID1630442	Antiproliferative activity against human gefitinib-resistant PC9 cells harboring EGFR T790M mutant assessed as cell viability measured after 24 hrs	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID1311779	Antiinflammatory activity against LPS-stimulated mouse RAW264.7 cells assessed as COX2 levels at 5 umol/L by ELISA (Rvb = 159.64 +/- 13.56 pg/mL)	2016	Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15	Anti-inflammatory polyphenol constituents derived from Cissus pteroclada Hayata.
AID1630437	Decrease in EGFR level in human NCI-H460 cells harboring wild-type EGFR at 30 and 60 uM measured after 24 hrs by immunoblotting analysis	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID732559	Cytotoxicity against mouse RAW264.7 cells assessed as decreased cell viability at 50 uM after 6 hrs by MTT assay	2013	Journal of medicinal chemistry, Feb-14, Volume: 56, Issue:3	A novel semisynthetic flavonoid 7-O-galloyltaxifolin upregulates heme oxygenase-1 in RAW264.7 cells via MAPK/Nrf2 pathway.
AID1187067	Inhibition of insulin fibril formation (unknown origin) assessed as turbidity at 1:10 insulin to compound ratio at pH2 up to 12 hrs by UV/vis spectrometry	2014	European journal of medicinal chemistry, Oct-06, Volume: 85	Gallic acid, one of the components in many plant tissues, is a potential inhibitor for insulin amyloid fibril formation.
AID711620	Increase of lifespan of L4 larvae of Caenorhabditis elegans at 300 uM after 8 hrs in presence of H2O2	2011	Journal of natural products, Aug-26, Volume: 74, Issue:8	Diversity of polyphenol action in Caenorhabditis elegans: between toxicity and longevity.
AID401061	Antioxidant activity assessed as DPPH free radical scavenging activity	1998	Journal of natural products, May, Volume: 61, Issue:5	Antioxidant flavonoid glycosides from Daphniphyllum calycinum.
AID462272	Inhibition of human CA3 by stopped-flow CO2 hydration assay	2010	Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6	Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids.
AID1524671	Covalent inhibition of purified Sporosarcinia pasteurii urease by phenol red based method
AID1664684	Inhibition of alpha-synuclein (unknown origin) aggregation incubated for 3 days by thioflavin T based fluorescence assay	2020	Bioorganic & medicinal chemistry, 08-01, Volume: 28, Issue:15	Amide derivatives of Gallic acid: Design, synthesis and evaluation of inhibitory activities against in vitro α-synuclein aggregation.
AID1176782	Antioxidant activity assessed as DPPH radical scavenging activity after 30 mins by UV-spectrophotometry	2015	Journal of natural products, Jan-23, Volume: 78, Issue:1	Unusual C,O-Fused Glycosylapigenins from Serjania marginata Leaves.
AID1491525	Cytoprotective activity against H2O2-induced apoptosis in rat PC12 cells assessed as necrotic cells at 10 uM preincubated for 0.5 hrs followed by H2O2 addition measured after 2 hrs by Annexin V-FITC/propidium iodide staining based flow cytometry (Rvb = 2%	2017	European journal of medicinal chemistry, Sep-29, Volume: 138	Synthesis and anti-oxidant activity evaluation of (±)-Anastatins A, B and their analogs.
AID1337777	Antioxidant activity assessed as vitamin-c equivalent measured after 20 mins by FRAP assay	2017	European journal of medicinal chemistry, Jan-05, Volume: 125	Synthesis and antioxidant evaluation of desmethylxanthohumol analogs and their dimers.
AID1186044	Cytotoxicity against human HL60 cells assessed as cell survival at 50 uM after 72 hrs by CCK8 assay	2014	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 24, Issue:17	Phytochemical analysis and antileukemic activity of polyphenolic constituents of Toona sinensis.
AID1588066	Inhibition of catalytic activity of human recombinant FLAG-tagged ppGalNAcT2 expressed in HEK293T cells and using 5-FAM labelled-EA2 peptide as substrate incubated for 30 mins by HPLC-based enzyme assay	2019	Bioorganic & medicinal chemistry, 08-01, Volume: 27, Issue:15	Inhibition of polypeptide N-acetyl-α-galactosaminyltransferases is an underlying mechanism of dietary polyphenols preventing colorectal tumorigenesis.
AID1809201	Induction of osteoblast differentiation in rat Calvaria osteoblast cells measured assessed as increase in alkaline phosphatase activity at 10 pM incubated for 48 hrs using PNPP as substrate
AID400992	Inhibition of AMV reverse transcriptase activity assessed as incorporation of dGMP in poly(rC)-oligo(dG) at 100 uM
AID1110808	Antimicrobial activity against Corynebacterium accolens at 100 ug after 24 hr by disk diffusion method	2005	Phytochemistry, Jan, Volume: 66, Issue:2	Bioactive ellagitannins from Cunonia macrophylla, an endemic Cunoniaceae from New Caledonia.
AID1105397	Antioxidant activity assessed as DPPH free radical scavenging activity after 20 min by UV-Vis spectrophotometric analysis	2013	European journal of medicinal chemistry, Jan, Volume: 59	Microwave synthesis, characterization and bio-efficacy evaluation of novel chalcone based 6-carbethoxy-2-cyclohexen-1-one and 2H-indazol-3-ol derivatives.
AID381930	Induction of apoptosis in human CEM cells assessed as internucleosomal breakdown of DNA chromatin at 100 uM	2008	Bioorganic & medicinal chemistry, Apr-01, Volume: 16, Issue:7	Ester derivatives of gallic acid with potential toxicity toward L1210 leukemia cells.
AID1311767	Antiinflammatory activity against LPS-stimulated mouse RAW264.7 cells assessed as PGE2 levels at 25 umol/L by ELISA (Rvb = 33.2 +/- 2.33 pg/mL)	2016	Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15	Anti-inflammatory polyphenol constituents derived from Cissus pteroclada Hayata.
AID1310995	Cytotoxicity against human A549 cells assessed as reduction in cell viability measured after 48 hrs by FMCA assay	2016	European journal of medicinal chemistry, Aug-25, Volume: 119	On the vasoprotective mechanisms underlying novel β-phosphorylated nitrones: Focus on free radical characterization, scavenging and NO-donation in a biological model of oxidative stress.
AID1239713	Anti-platelet activity in rat platelet rich plasma assessed as inhibition of ADP and calcium-induced platelet aggregation at 100 uM pre-incubated at 37 degC for 10 mins and measured 30 mins after ADP and calcium addition	2015	Bioorganic & medicinal chemistry letters, Aug-15, Volume: 25, Issue:16	Potential therapeutic agents for circulatory diseases from Bauhinia glauca Benth.subsp. pernervosa. (Da Ye Guan Men).
AID417963	Antimicrobial activity against Aspergillus fumigatus after 48 hrs by broth microdilution technique	2009	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 19, Issue:6	Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi.
AID1592386	Electrochemical behavior of the compound assessed as redox potential corrected toward saturated Ag/AgCl reference electrode by differential pulse voltammetry
AID1399447	Induction of apoptosis in human A549 cells assessed as live cells at 2.5 uM after 48 hrs by Annexin-V-FITC/propidium iodide staining based flow cytometry (Rvb = 75.2%)	2018	Bioorganic & medicinal chemistry, 08-15, Volume: 26, Issue:15	Anti-angiogenic and anticancer effects of baicalein derivatives based on transgenic zebrafish model.
AID548181	Antioxidant activity assessed as DPPH radical scavenging activity	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Benzophenones and biflavonoids from Rheedia edulis.
AID1064677	Antioxidant activity of the compound assessed as inhibition of ABTS radicals at 33 uM after 20 mins by spectrophotometric analysis	2014	Bioorganic & medicinal chemistry, Feb-01, Volume: 22, Issue:3	Synthesis, modelling and biological characterization of 3-substituted-1H-indoles as ligands of GluN2B-containing N-methyl-d-aspartate receptors.
AID280291	Inhibition of human P-selectin after 2 hrs	2007	Journal of medicinal chemistry, Mar-22, Volume: 50, Issue:6	Rational design of novel, potent small molecule pan-selectin antagonists.
AID400990	Inhibition of AMV reverse transcriptase activity assessed as incorporation of dGMP in poly(rC)-oligo(dG) at 1 uM
AID614099	Antioxidant activity assessed as H2O2 scavenging activity at 12.5 to 250 ug/mL after 30 mins by spectrophotometric analysisic analysis	2011	Bioorganic & medicinal chemistry, Sep-01, Volume: 19, Issue:17	Tylosema esculentum extractives and their bioactivity.
AID642414	Estrogenic activity at ERalpha in human MVLN cells at 100 ug/mL after 24 hrs by luciferase reporter gene assay relative to E2	2012	Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1	Discovery of estrogen receptor α modulators from natural compounds in Si-Wu-Tang series decoctions using estrogen-responsive MCF-7 breast cancer cells.
AID1491529	Cytoprotective activity against H2O2-induced apoptosis in rat PC12 cells assessed as necrotic cells at 100 uM preincubated for 0.5 hrs followed by H2O2 addition measured after 2 hrs by Annexin V-FITC/propidium iodide staining based flow cytometry (Rvb = 2	2017	European journal of medicinal chemistry, Sep-29, Volume: 138	Synthesis and anti-oxidant activity evaluation of (±)-Anastatins A, B and their analogs.
AID388743	Antioxidant activity assessed as DPPH radical scavenging activity after 20 mins	2008	Bioorganic & medicinal chemistry, Dec-01, Volume: 16, Issue:23	Inhibition of aldose reductase from cataracted eye lenses by finger millet (Eleusine coracana) polyphenols.
AID1082339	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 2% under dark conditions measured 5 to 60 min post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID417959	Antifungal activity against Candida albicans after 48 hrs by broth microdilution technique	2009	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 19, Issue:6	Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi.
AID417966	Antimicrobial activity against Microsporum gypseum after 48 hrs by broth microdilution technique	2009	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 19, Issue:6	Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi.
AID711619	Increase of lifespan of L4 larvae of Caenorhabditis elegans assessed as lifespan increasing concentration after 8 hrs	2011	Journal of natural products, Aug-26, Volume: 74, Issue:8	Diversity of polyphenol action in Caenorhabditis elegans: between toxicity and longevity.
AID1101855	Antifungal activity against Saccharomyces cerevisiae ATCC 7754 after 48 hr by microdilution method	2002	Journal of agricultural and food chemistry, Jul-03, Volume: 50, Issue:14	Molecular design of antifungal agents.
AID1631496	Antioxidant activity assessed as DPPH radical scavenging activity after 5 mins by spectrophotometric analysis	2016	Journal of natural products, Apr-22, Volume: 79, Issue:4	Minor Pyranonaphthoquinones from the Apothecia of the Lichen Ophioparma ventosa.
AID730116	Antioxidant activity assessed as DPPH radical scavenging activity at 0.1 mM	2013	Bioorganic & medicinal chemistry, Feb-15, Volume: 21, Issue:4	N-(Phenoxyalkyl)amides as MT(1) and MT(2) ligands: antioxidant properties and inhibition of Ca(2+)/CaM-dependent kinase II.
AID732060	Cytotoxicity against human HL60 cells	2013	European journal of medicinal chemistry, Feb, Volume: 60	Alkyl esters of gallic acid as anticancer agents: a review.
AID83434	Inhibitory concentration against polymerization in A17 double mutant HIV-1 RT using a template primer of poly rC/dG12-18 and [3H]dGTP; ND is not determined	2001	Bioorganic & medicinal chemistry letters, Oct-22, Volume: 11, Issue:20	Simplified catechin-gallate inhibitors of HIV-1 reverse transcriptase.
AID1197645	Antiviral activity against influenza A virus (H1N1)	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID1311772	Antiinflammatory activity against LPS-stimulated mouse RAW264.7 cells assessed as iNOS levels at 5 umol/L by ELISA (Rvb = 31.63 +/- 3.26 U/mL)	2016	Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15	Anti-inflammatory polyphenol constituents derived from Cissus pteroclada Hayata.
AID1082336	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 0.25% under dark conditions measured 5 to 60 min post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID1055137	Inhibition of reduced carboxymethylated-kappa-casein (unknown origin) conversion to amyloid fibrils at 1:0.1 protein to compound molar ratio after 1000 mins by thioflavin T fluorescence assay relative to control	2013	Bioorganic & medicinal chemistry letters, Dec-01, Volume: 23, Issue:23	Gallic acid is the major component of grape seed extract that inhibits amyloid fibril formation.
AID1083162	Antifungal activity against Neofusicoccum parvum Bp0014 assessed as growth inhibition measured after 1 to 10 days	2012	Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48	Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID1167300	Antioxidant activity assessed as DPPH radical scavenging activity incubated at room temperature for 20 mins by UV-visible spectrophotometry	2014	Bioorganic & medicinal chemistry letters, Nov-01, Volume: 24, Issue:21	Design, synthesis and exploring the quantitative structure-activity relationship of some antioxidant flavonoid analogues.
AID1082335	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 0.125% under dark conditions measured 5 to 60 min post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID462271	Inhibition of human CA2 by stopped-flow CO2 hydration assay	2010	Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6	Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids.
AID711605	Reduction of frequency of pharyngeal pumping in Caenorhabditis elegans at 300 uM on 3rd to 9th day of adulthood	2011	Journal of natural products, Aug-26, Volume: 74, Issue:8	Diversity of polyphenol action in Caenorhabditis elegans: between toxicity and longevity.
AID315608	Growth inhibition of human BGC823 cells at 50 uM after 72 hrs by MTT assay relative to control	2008	Bioorganic & medicinal chemistry, Feb-01, Volume: 16, Issue:3	Studies on the chemical constituents and anticancer activity of Saxifraga stolonifera (L) Meeb.
AID344830	Antioxidant activity assessed as DPPH radical scavenging activity at 50 uM	2008	Bioorganic & medicinal chemistry, Nov-15, Volume: 16, Issue:22	New diterpenoids and the bioactivity of Erythrophleum fordii.
AID1110809	Antimicrobial activity against Staphylococcus aureus at 100 ug after 24 hr by disk diffusion method	2005	Phytochemistry, Jan, Volume: 66, Issue:2	Bioactive ellagitannins from Cunonia macrophylla, an endemic Cunoniaceae from New Caledonia.
AID1592385	Electrochemical behavior of the compound assessed as redox potential corrected toward saturated Ag/AgCl reference electrode by cyclic voltammetry
AID710235	Antioxidant activity assessed as scavenging of glucose oxidase-generated H2O2 and hydroxyl radicals by chemiluminescence assay	2012	Journal of medicinal chemistry, Dec-13, Volume: 55, Issue:23	Carbamate derivatives of indolines as cholinesterase inhibitors and antioxidants for the treatment of Alzheimer's disease.
AID1762129	Cytotoxicity against human ER-positive MCF7 cells assessed as decrease in cell proliferation at 12.5 to 100 uM incubated for 24 hrs	2021	Bioorganic & medicinal chemistry letters, 05-15, Volume: 40	Estrogenic activity of ethyl gallate and its potential use in hormone replacement therapy.
AID380376	DPPH radical scavenging activity at 5 uM after 30 mins by spectrophotometric assay	2000	Journal of natural products, Jun, Volume: 63, Issue:6	Galloylglucosides from berries of Pimenta dioica.
AID1256913	Inhibition of human IDH1 expressed in IPTG-induced Escherichia coli BL21 cells assessed as reduction of NADP+ to NADPH after 5 mins by spectrophotometry	2015	Bioorganic & medicinal chemistry letters, Dec-01, Volume: 25, Issue:23	Discovery of α-mangostin as a novel competitive inhibitor against mutant isocitrate dehydrogenase-1.
AID1105378	Antioxidant activity assessed as DPPH free radical scavenging activity at 0.2 ug/mL after 20 min by UV-Vis spectrophotometric analysis	2013	European journal of medicinal chemistry, Jan, Volume: 59	Microwave synthesis, characterization and bio-efficacy evaluation of novel chalcone based 6-carbethoxy-2-cyclohexen-1-one and 2H-indazol-3-ol derivatives.
AID1187072	Inhibition of insulin fibril formation (unknown origin) assessed as decrease in ThT fluorescence at 1:50 insulin to compound ratio at pH2 up to 12 hrs by ThT binding assay	2014	European journal of medicinal chemistry, Oct-06, Volume: 85	Gallic acid, one of the components in many plant tissues, is a potential inhibitor for insulin amyloid fibril formation.
AID730114	Antioxidant activity assessed as DPPH radical scavenging activity at 1 mM	2013	Bioorganic & medicinal chemistry, Feb-15, Volume: 21, Issue:4	N-(Phenoxyalkyl)amides as MT(1) and MT(2) ligands: antioxidant properties and inhibition of Ca(2+)/CaM-dependent kinase II.
AID1762124	Cytotoxicity against human ER-positive MCF7 cells assessed as cell proliferation at 50 uM incubated for 144 hrs by Soto's E-screen assay relative to control	2021	Bioorganic & medicinal chemistry letters, 05-15, Volume: 40	Estrogenic activity of ethyl gallate and its potential use in hormone replacement therapy.
AID397155	Antioxidant activity against Cu2+-induced lipid peroxidation in human plasma LDL at 0.2 umol/L preincubated for 1 hr before Cu2+ challenge	2001	Journal of natural products, Apr, Volume: 64, Issue:4	Specific antioxidant activity of caffeoyl derivatives and other natural phenolic compounds: LDL protection against oxidation and decrease in the proinflammatory lysophosphatidylcholine production.
AID381925	Decrease in cytoplasmic glutathione level in mouse L1210 cells	2008	Bioorganic & medicinal chemistry, Apr-01, Volume: 16, Issue:7	Ester derivatives of gallic acid with potential toxicity toward L1210 leukemia cells.
AID1055131	Effect on RCM-kappa-casein-induced cytotoxicity against rat PC12 cells at 1:0.1 to 1:0.5 protein to compound molar ratio after 48 hrs by MTT assay	2013	Bioorganic & medicinal chemistry letters, Dec-01, Volume: 23, Issue:23	Gallic acid is the major component of grape seed extract that inhibits amyloid fibril formation.
AID401337	Antioxidant activity assessed by hydroxyl radical scavenging assay	1996	Journal of natural products, Feb, Volume: 59, Issue:2	Natural polyphenols (vegetable tannins) as drugs: possible modes of action.
AID1083156	Antifungal activity against Diplodia seriata LAT28 assessed as growth inhibition measured after 1 to 10 days	2012	Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48	Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID730113	Antioxidant activity assessed as DPPH radical scavenging activity	2013	Bioorganic & medicinal chemistry, Feb-15, Volume: 21, Issue:4	N-(Phenoxyalkyl)amides as MT(1) and MT(2) ligands: antioxidant properties and inhibition of Ca(2+)/CaM-dependent kinase II.
AID1630411	Antiproliferative activity against human A549 cells harboring wild-type EGFR assessed as cell viability at 30 and 60 uM measured after 24 hrs	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID400991	Inhibition of AMV reverse transcriptase activity assessed as incorporation of dGMP in poly(rC)-oligo(dG) at 10 uM
AID1540296	Cytotoxicity against mouse RAW264.7 cells after 24 hrs by MTT assay
AID624606	Specific activity of expressed human recombinant UGT1A1	2000	Annual review of pharmacology and toxicology, , Volume: 40	Human UDP-glucuronosyltransferases: metabolism, expression, and disease.
AID105091	Percent reduction in cell viability of MOLT-3 cells 72 hr after incubation with the compound	2003	Journal of medicinal chemistry, Dec-04, Volume: 46, Issue:25	Anticancer activity of phenolic acids of natural or synthetic origin: a structure-activity study.
AID380377	DPPH radical scavenging activity at 2.5 uM after 30 mins by spectrophotometric assay	2000	Journal of natural products, Jun, Volume: 63, Issue:6	Galloylglucosides from berries of Pimenta dioica.
AID355135	Antimicrobial activity against Porphyromonas gingivalis ATCC 33277 by disk diffusion method	1996	Journal of natural products, Oct, Volume: 59, Issue:10	Compounds from Syzygium aromaticum possessing growth inhibitory activity against oral pathogens.
AID462270	Inhibition of human CA1 by stopped-flow CO2 hydration assay	2010	Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6	Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids.
AID614102	Antimicrobial activity against Pseudomonas aeruginosa NCTC 10332 after 24 hrs using thiazoyl blue by agar overlay bioautography method	2011	Bioorganic & medicinal chemistry, Sep-01, Volume: 19, Issue:17	Tylosema esculentum extractives and their bioactivity.
AID1311776	Inhibition of NFkappaB signaling pathway in LPS-stimulated mouse RAW264.7 cells assessed as protein levels at 25 umol/L by ELISA (Rvb = 1.23 +/- 0.06 pg/mL)	2016	Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15	Anti-inflammatory polyphenol constituents derived from Cissus pteroclada Hayata.
AID711609	Reduction of initial reproduction rate in Caenorhabditis elegans assessed as first egg deposition at 300 uM after 85 hrs	2011	Journal of natural products, Aug-26, Volume: 74, Issue:8	Diversity of polyphenol action in Caenorhabditis elegans: between toxicity and longevity.
AID417965	Antimicrobial activity against Aspergillus niger after 48 hrs by broth microdilution technique	2009	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 19, Issue:6	Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi.
AID355138	Antimicrobial activity against Actinomyces viscosus W1053 by disk diffusion method	1996	Journal of natural products, Oct, Volume: 59, Issue:10	Compounds from Syzygium aromaticum possessing growth inhibitory activity against oral pathogens.
AID1311781	Antiinflammatory activity against LPS-stimulated mouse RAW264.7 cells assessed as COX2 levels at 50 umol/L by ELISA (Rvb = 159.64 +/- 13.56 pg/mL)	2016	Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15	Anti-inflammatory polyphenol constituents derived from Cissus pteroclada Hayata.
AID1759524	Nephroprotective activity in Sprague-Dawley rat assessed as reduction in FK506-induced kidney dysfunction by measuring decrease in serum creatinine level measured after 14 days	2021	Bioorganic & medicinal chemistry letters, 06-01, Volume: 41	Identification of gallic acid as a active ingredient of Syzygium aromaticum against tacrolimus-induced damage in renal epithelial LLC-PK1 cells and rat kidney.
AID336478	Inhibition of COX2 at 100 uM by scintillation proximity assay	2002	Journal of natural products, Nov, Volume: 65, Issue:11	Screening of ubiquitous plant constituents for COX-2 inhibition with a scintillation proximity based assay.
AID357307	Inhibition of C-terminal hexahistidine-tagged rat recombinant squalene epoxidase without N-terminal putative membrane domain expressed in Escherichia coli	2001	Journal of natural products, Aug, Volume: 64, Issue:8	Ellagitannins and hexahydroxydiphenoyl esters as inhibitors of vertebrate squalene epoxidase.
AID763542	Antioxidant activity assessed as inhibition of ABTS free radical generation at 17 uM after 20 mins by UV spectrophotometric analysis relative to control	2013	Bioorganic & medicinal chemistry, Aug-01, Volume: 21, Issue:15	Indole derivatives as dual-effective agents for the treatment of neurodegenerative diseases: synthesis, biological evaluation, and molecular modeling studies.
AID1082346	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 5% under light conditions measured 5 to 60 min post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID1311000	Potentiation of SNP-induced vasorelaxant activity in Sprague-Dawley rat endothelium-intact aortic rings assessed as SNP EC50 for reduction in L-phenylephrine hydrochloride-induced contraction by (Rvb = 7.98 +/- 0.02 No_unit)	2016	European journal of medicinal chemistry, Aug-25, Volume: 119	On the vasoprotective mechanisms underlying novel β-phosphorylated nitrones: Focus on free radical characterization, scavenging and NO-donation in a biological model of oxidative stress.
AID462274	Inhibition of human CA5A by stopped-flow CO2 hydration assay	2010	Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6	Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids.
AID228902	Effective dose required for antioxidant activity was measured as dose giving 50% decolorization of 2,2-diphenyl-1-picryl-hydrazyl (DPPH)	2002	Bioorganic & medicinal chemistry letters, Jun-17, Volume: 12, Issue:12	Synthesis and biological activity of polygalloyl-dendrimers as stable tannic acid mimics.
AID381918	Cytotoxicity against mouse L1210 cells after 72 hrs by MTT assay	2008	Bioorganic & medicinal chemistry, Apr-01, Volume: 16, Issue:7	Ester derivatives of gallic acid with potential toxicity toward L1210 leukemia cells.
AID768928	Inhibition of human thrombin amidolytic activity using D-Phe-Pip-Arg-pNA as substrate at 0.1 to 1000 uM preincubated for 10 mins followed by substrate addition measured every 12 secs for 10 mins by spectrophotometric analysis	2014	Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, , Volume: 23	Thrombin inhibitory activity of some polyphenolic compounds.
AID1809200	Induction of osteoblast differentiation in rat Calvaria osteoblast cells measured assessed as increase in alkaline phosphatase activity at 1 pM incubated for 48 hrs using PNPP as substrate
AID732054	Cytotoxicity against human A549 cells	2013	European journal of medicinal chemistry, Feb, Volume: 60	Alkyl esters of gallic acid as anticancer agents: a review.
AID232817	The degree of collagen cross-linking by hydrothermal shrinkage temperature was determined	2002	Bioorganic & medicinal chemistry letters, Jun-17, Volume: 12, Issue:12	Synthesis and biological activity of polygalloyl-dendrimers as stable tannic acid mimics.
AID1873810	Inhibition of amyloid beta 1 to 42 aggregation (unknown origin) incubated for 24 hrs by inverted fluorescence microscopic analysis relative to control	2022	Bioorganic & medicinal chemistry, 08-15, Volume: 68	Chemical analysis of amyloid β aggregation inhibitors derived from Geranium thunbergii.
AID1490876	Induction of H2O2-inactivated bovine milk lactoperoxidase pseudo-halogenating activity assessed as increase in hypothiocyanate formation by measuring substrate Km using thiocyanate as substrate by Lineweaver-Burk plot	2017	Journal of natural products, 05-26, Volume: 80, Issue:5	Tannins and Tannin-Related Derivatives Enhance the (Pseudo-)Halogenating Activity of Lactoperoxidase.
AID1197643	Antiviral activity against sindbis virus	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID1630412	Antiproliferative activity against human NCI-H460 cells harboring wild-type EGFR assessed as cell viability at 30 and 60 uM measured after 24 hrs	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID1055139	Inhibition of reduced carboxymethylated-kappa-casein (unknown origin) conversion to amyloid fibrils at 1:1 protein to compound molar ratio after 1000 mins by thioflavin T fluorescence assay relative to control	2013	Bioorganic & medicinal chemistry letters, Dec-01, Volume: 23, Issue:23	Gallic acid is the major component of grape seed extract that inhibits amyloid fibril formation.
AID1197647	Antiviral activity against feline coronavirus	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID1674380	Antifungal activity against Candida albicans SC5314 by CLSI protocol-based broth serial dilution method
AID462281	Inhibition of human CA14 by stopped-flow CO2 hydration assay	2010	Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6	Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids.
AID555340	Effect on growth in Staphylococcus aureus MN8 at 0.50 % after 24 hrs (Rvb = 100%)	2009	Antimicrobial agents and chemotherapy, May, Volume: 53, Issue:5	Surfactants, aromatic and isoprenoid compounds, and fatty acid biosynthesis inhibitors suppress Staphylococcus aureus production of toxic shock syndrome toxin 1.
AID732052	Cytotoxicity against mouse L929 cells	2013	European journal of medicinal chemistry, Feb, Volume: 60	Alkyl esters of gallic acid as anticancer agents: a review.
AID314588	Antagonist activity at LuxP receptor in Vibrio harveyi MM32 assessed as inhibition of autoinducer-2-mediated quorum sensing after 3 to 4 hrs	2008	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 18, Issue:5	Pyrogallol and its analogs can antagonize bacterial quorum sensing in Vibrio harveyi.
AID1064676	Antioxidant activity of the compound assessed as inhibition of ABTS radicals at 17 uM after 20 mins by spectrophotometric analysis	2014	Bioorganic & medicinal chemistry, Feb-01, Volume: 22, Issue:3	Synthesis, modelling and biological characterization of 3-substituted-1H-indoles as ligands of GluN2B-containing N-methyl-d-aspartate receptors.
AID710230	Antioxidant activity of the compound assessed as DPPH radical scavenging at 10 uM after 30 secs by spectrophotometry	2012	Journal of medicinal chemistry, Dec-13, Volume: 55, Issue:23	Carbamate derivatives of indolines as cholinesterase inhibitors and antioxidants for the treatment of Alzheimer's disease.
AID1630409	Antiproliferative activity against human NCI-H1975 cells harboring EGFR-mutant assessed as cell viability measured after 24 hrs	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID732550	Activation of Nrf2 in mouse RAW264.7 cells assessed as upregulation of Hmox1 gene expression at 50 uM after 6 hrs by real-time PCR analysis relative to GAPDH mRNA expression	2013	Journal of medicinal chemistry, Feb-14, Volume: 56, Issue:3	A novel semisynthetic flavonoid 7-O-galloyltaxifolin upregulates heme oxygenase-1 in RAW264.7 cells via MAPK/Nrf2 pathway.
AID671761	Inhibition of SARS coronavirus nsP13 helicase activity expressed in Escherichia coli Rosetta assessed inhibition of DNA unwinding activity at 10 uM by FRET assay	2012	Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12	Identification of myricetin and scutellarein as novel chemical inhibitors of the SARS coronavirus helicase, nsP13.
AID1228618	Antioxidant activity assessed as DPPH radical-scavenging activity incubated for 30 mins by spectrophotometry	2015	Journal of natural products, May-22, Volume: 78, Issue:5	Anti-inflammatory Hydrolyzable Tannins from Myricaria bracteata.
AID614101	Antimicrobial activity against Bacillus subtilis ATCC 6633 after 24 hrs using thiazoyl blue by agar overlay bioautography method	2011	Bioorganic & medicinal chemistry, Sep-01, Volume: 19, Issue:17	Tylosema esculentum extractives and their bioactivity.
AID1337776	Antioxidant activity against H2O2-induced oxidative stress in rat PC12 cells assessed as GSH level per gram of protein at 10 uM pretreated for 0.5 hrs followed by H2O2 challenge measured after 2 hrs by GSH peroxidase assay (Rvb = 59.93 umol)	2017	European journal of medicinal chemistry, Jan-05, Volume: 125	Synthesis and antioxidant evaluation of desmethylxanthohumol analogs and their dimers.
AID1110810	Antimicrobial activity against Pectobacterium carotovorum at 100 ug after 24 hr by disk diffusion method	2005	Phytochemistry, Jan, Volume: 66, Issue:2	Bioactive ellagitannins from Cunonia macrophylla, an endemic Cunoniaceae from New Caledonia.
AID1630420	Increase in cleaved caspase3 level in human NCI-H460 cells harboring wild-type EGFR at 30 and 60 uM by immunoblotting analysis	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID381924	Genotoxicity against african green monkey VERO cells	2008	Bioorganic & medicinal chemistry, Apr-01, Volume: 16, Issue:7	Ester derivatives of gallic acid with potential toxicity toward L1210 leukemia cells.
AID1491524	Cytoprotective activity against H2O2-induced apoptosis in rat PC12 cells assessed as late apoptotic cells at 10 uM preincubated for 0.5 hrs followed by H2O2 addition measured after 2 hrs by Annexin V-FITC/propidium iodide staining based flow cytometry (Rv	2017	European journal of medicinal chemistry, Sep-29, Volume: 138	Synthesis and anti-oxidant activity evaluation of (±)-Anastatins A, B and their analogs.
AID977599	Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	2013	Molecular pharmacology, Jun, Volume: 83, Issue:6	Structure-based identification of OATP1B1/3 inhibitors.
AID378648	Antioxidant activity assessed as DPPH radical scavenging activity after 30 mins	2000	Journal of natural products, Dec, Volume: 63, Issue:12	Activity-guided isolation of antioxidative constituents of Cotinus coggygria.
AID1105373	Antioxidant activity assessed as DPPH free radical scavenging activity at 3 ug/mL after 20 min by UV-Vis spectrophotometric analysis	2013	European journal of medicinal chemistry, Jan, Volume: 59	Microwave synthesis, characterization and bio-efficacy evaluation of novel chalcone based 6-carbethoxy-2-cyclohexen-1-one and 2H-indazol-3-ol derivatives.
AID338980	Inhibition of ACE by fluorometric assay
AID1311765	Antiinflammatory activity against LPS-stimulated mouse RAW264.7 cells assessed as IL1beta levels at 50 umol/L by ELISA (Rvb = 8.70 +/- 0.365 pg/mL)	2016	Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15	Anti-inflammatory polyphenol constituents derived from Cissus pteroclada Hayata.
AID1491527	Cytoprotective activity against H2O2-induced apoptosis in rat PC12 cells assessed as early apoptotic cells at 100 uM preincubated for 0.5 hrs followed by H2O2 addition measured after 2 hrs by Annexin V-FITC/propidium iodide staining based flow cytometry (	2017	European journal of medicinal chemistry, Sep-29, Volume: 138	Synthesis and anti-oxidant activity evaluation of (±)-Anastatins A, B and their analogs.
AID1491522	Cytoprotective activity against H2O2-induced apoptosis in rat PC12 cells assessed as live cells at 10 uM preincubated for 0.5 hrs followed by H2O2 addition measured after 2 hrs by Annexin V-FITC/propidium iodide staining based flow cytometry (Rvb = 37.3%)	2017	European journal of medicinal chemistry, Sep-29, Volume: 138	Synthesis and anti-oxidant activity evaluation of (±)-Anastatins A, B and their analogs.
AID378878	Antioxidant activity assessed as DPPH free radical scavenging activity	2000	Journal of natural products, Jan, Volume: 63, Issue:1	Acylated flavonol glycosides from the flower of Inula britannica.
AID417962	Antifungal activity against Cryptococcus neoformans after 48 hrs by broth microdilution technique	2009	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 19, Issue:6	Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi.
AID1630416	Induction of apoptosis in human NCI-H460 cells harboring wild-type EGFR assessed as cell death at 30 and 60 uM measured after 24 hrs by Annexin-V/PI staining based analysis	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID711621	Increase of lifespan of L4 larvae of Caenorhabditis elegans at 300 uM at 35 degC after 8 hrs	2011	Journal of natural products, Aug-26, Volume: 74, Issue:8	Diversity of polyphenol action in Caenorhabditis elegans: between toxicity and longevity.
AID1083154	Antifungal activity against Diplodia seriata BoF98-1 assessed as growth inhibition measured after 1 to 10 days	2012	Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48	Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID1105371	Antioxidant activity assessed as DPPH free radical scavenging activity at 4 ug/mL after 20 min by UV-Vis spectrophotometric analysis	2013	European journal of medicinal chemistry, Jan, Volume: 59	Microwave synthesis, characterization and bio-efficacy evaluation of novel chalcone based 6-carbethoxy-2-cyclohexen-1-one and 2H-indazol-3-ol derivatives.
AID1311763	Antiinflammatory activity against LPS-stimulated mouse RAW264.7 cells assessed as IL1beta levels at 5 umol/L by ELISA (Rvb = 8.70 +/- 0.365 pg/mL)	2016	Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15	Anti-inflammatory polyphenol constituents derived from Cissus pteroclada Hayata.
AID357365	Antioxidant activity assessed as DPPH free radical scavenging activity after 30 mins	2001	Journal of natural products, Aug, Volume: 64, Issue:8	Samioside, a new phenylethanoid glycoside with free-radical scavenging and antimicrobial activities from Phlomis samia.
AID1083155	Antifungal activity against Diplodia seriata BoF99-1 assessed as growth inhibition measured after 1 to 10 days	2012	Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48	Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID711601	Increase of mean lifespan of L4 larvae of Caenorhabditis elegans harboring eat-2 (ad465) at 300 uM after 8 hrs	2011	Journal of natural products, Aug-26, Volume: 74, Issue:8	Diversity of polyphenol action in Caenorhabditis elegans: between toxicity and longevity.
AID1630428	Induction of apoptosis in human NCI-H1650 cells harboring EGFR-mutant assessed as cell death at 60 uM in presence of NAC	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID1311759	Cytotoxicity against LPS-stimulated mouse RAW264.7 cells assessed as reduction in cell viability at 50 umol/L after 24 hrs by MTT assay	2016	Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15	Anti-inflammatory polyphenol constituents derived from Cissus pteroclada Hayata.
AID1470585	Antioxidant activity assessed as DPPH free radical scavenging activity at 100 ppm after 30 mins in dark by spectrophotometric method relative to control	2017	European journal of medicinal chemistry, May-26, Volume: 132	Recent synthetic and medicinal perspectives of dihydropyrimidinones: A review.
AID1630439	Inhibition of EGFR-mediated ERK phosphorylation in human NCI-H460 cells harboring wild-type EGFR at 30 and 60 uM measured after 24 hrs by immunoblotting analysis	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID1197642	Antiviral activity against reovirus	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID1197649	Antiviral activity against chikungunya virus	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID1337775	Antioxidant activity against H2O2-induced oxidative stress in rat PC12 cells assessed as 8-OHdG level at 10 uM pretreated for 0.5 hrs followed by H2O2 challenge measured after 2 hrs (Rvb = 123.97 ng/L)	2017	European journal of medicinal chemistry, Jan-05, Volume: 125	Synthesis and antioxidant evaluation of desmethylxanthohumol analogs and their dimers.
AID385427	Inhibition of soybean 15-lipoxygenase	2008	Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8	Inhibition of 15-lipoxygenase-catalysed oxygenation of arachidonic acid by substituted benzoic acids.
AID355136	Antimicrobial activity against Prevotella intermedia by disk diffusion method	1996	Journal of natural products, Oct, Volume: 59, Issue:10	Compounds from Syzygium aromaticum possessing growth inhibitory activity against oral pathogens.
AID1491523	Cytoprotective activity against H2O2-induced apoptosis in rat PC12 cells assessed as early apoptotic cells at 10 uM preincubated for 0.5 hrs followed by H2O2 addition measured after 2 hrs by Annexin V-FITC/propidium iodide staining based flow cytometry (R	2017	European journal of medicinal chemistry, Sep-29, Volume: 138	Synthesis and anti-oxidant activity evaluation of (±)-Anastatins A, B and their analogs.
AID536052	Antioxidant activity assessed as DPPH free radical scavenging activity by measuring [DPPH]/antioxidant EC50 ratio measured every 5 mins for 1 hr	2010	Bioorganic & medicinal chemistry, Nov-15, Volume: 18, Issue:22	Synthesis and antioxidant properties of pulvinic acids analogues.
AID1705585	Cytoprotective activity against H2O2-induced cell death in human PC-12 cells assessed as cell viability at 10 uM incubated for 0.5 hrs followed by H2O2 stimulation and measured after 2 hrs by MTT assay	2020	European journal of medicinal chemistry, Dec-01, Volume: 207	Preparation, characterization, antioxidant evaluation of new curcumin derivatives and effects of forming HSA-bound nanoparticles on the stability and activity.
AID1873811	Inhibition of amyloid beta 1 to 42 aggregation (unknown origin) incubated for 24 hrs by ThT fluorescence assay	2022	Bioorganic & medicinal chemistry, 08-15, Volume: 68	Chemical analysis of amyloid β aggregation inhibitors derived from Geranium thunbergii.
AID1542227	Inhibition of synthetic AcPHF6 peptide aggregation in pH 7.4 phosphate buffer assessed as reduction in fluorescence intensity at 50 uM and measured every minute over 2 hrs with 5 secs shaking prior to each reading by ThT fluorescence assay	2019	European journal of medicinal chemistry, Apr-01, Volume: 167	Repurposing nitrocatechols: 5-Nitro-α-cyanocarboxamide derivatives of caffeic acid and caffeic acid phenethyl ester effectively inhibit aggregation of tau-derived hexapeptide AcPHF6.
AID397158	Antioxidant activity against AAPH-induced lipid peroxidation in human plasma LDL at 1 umol/L preincubated for 1 hr before AAPH challenge	2001	Journal of natural products, Apr, Volume: 64, Issue:4	Specific antioxidant activity of caffeoyl derivatives and other natural phenolic compounds: LDL protection against oxidation and decrease in the proinflammatory lysophosphatidylcholine production.
AID1630408	Inhibition of EGFR mutant-mediated AKT phosphorylation in human NCI-H1650 cells harboring EGFR-mutant at 30 and 60 uM measured after 24 hrs by immunoblotting analysis	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID1082337	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 0.5% under dark conditions measured 5 to 60 min post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID381920	Cytotoxicity against human CEM cells after 72 hrs by MTT assay	2008	Bioorganic & medicinal chemistry, Apr-01, Volume: 16, Issue:7	Ester derivatives of gallic acid with potential toxicity toward L1210 leukemia cells.
AID614098	Antioxidant activity assessed as DPPH radical scavenging activity after 30 mins by spectrophotometric analysisic analysis	2011	Bioorganic & medicinal chemistry, Sep-01, Volume: 19, Issue:17	Tylosema esculentum extractives and their bioactivity.
AID555373	Induction of toxin TSST-1 production in Staphylococcus aureus MN8 at 0.10 % after 24 hrs relative to control	2009	Antimicrobial agents and chemotherapy, May, Volume: 53, Issue:5	Surfactants, aromatic and isoprenoid compounds, and fatty acid biosynthesis inhibitors suppress Staphylococcus aureus production of toxic shock syndrome toxin 1.
AID1082338	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 1% under dark conditions measured 5 to 60 min post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID397159	Antioxidant activity against Cu2+-induced lipid peroxidation in human plasma LDL at 0.01 to 0.1 umol/L preincubated for 1 hr before Cu2+ challenge	2001	Journal of natural products, Apr, Volume: 64, Issue:4	Specific antioxidant activity of caffeoyl derivatives and other natural phenolic compounds: LDL protection against oxidation and decrease in the proinflammatory lysophosphatidylcholine production.
AID711622	Increase of lifespan of L4 larvae of Caenorhabditis elegans after 8 hrs in presence of H2O2	2011	Journal of natural products, Aug-26, Volume: 74, Issue:8	Diversity of polyphenol action in Caenorhabditis elegans: between toxicity and longevity.
AID732040	Inhibition of ADAM17 alpha-secretase activity in human UI87 cells using amyloid beta precursor protein as substrate at 40 ug/ml after 24 hrs by fluorimetric analysis	2013	European journal of medicinal chemistry, Feb, Volume: 60	Alkyl esters of gallic acid as anticancer agents: a review.
AID1129835	Inhibition of His-6-tagged Coxsackievirus B3 3C protease expressed in Escherichia coli BL21(DE3) using Asp-Glu-EDANS-(5-((2-aminoethyl)amino)naphthalene-1-sulfonic acid)-MSAIFQGPISK-DABCYL (4-((4-(dimethylamino)phenyl)azo)benzoic acid) as peptide substrat	2014	Bioorganic & medicinal chemistry, Apr-01, Volume: 22, Issue:7	Benzophenone C-glucosides and gallotannins from mango tree stem bark with broad-spectrum anti-viral activity.
AID616482	Antioxidant activity assessed as DPPH free radical scavenging activity	2011	Bioorganic & medicinal chemistry letters, Sep-15, Volume: 21, Issue:18	Synthesis and antioxygenic activities of seabuckthorn flavone-3-ols and analogs.
AID1424231	Antioxidant activity assessed as DPPH free radical scavenging activity	2017	European journal of medicinal chemistry, Jun-16, Volume: 133	Free radicals and polyphenols: The redox chemistry of neurodegenerative diseases.
AID1161575	Antioxidant activity assessed as total polyphenolics measured as gallic acid equivalent after 30 mins by Folin-Ciocalteu assay	2014	Bioorganic & medicinal chemistry, Oct-01, Volume: 22, Issue:19	Shogaol-huprine hybrids: dual antioxidant and anticholinesterase agents with β-amyloid and tau anti-aggregating properties.
AID1197639	Antiviral activity against human coxsackievirus B4	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID311580	Antioxidant activity assessed as DPPH radical scavenging activity	2007	Journal of natural products, Oct, Volume: 70, Issue:10	Structures and radical-scavenging activities of phenolic constituents from the bark of Picea jezoensis var. jezoensis.
AID400989	Inhibition of AMV reverse transcriptase activity assessed as incorporation of dGMP in poly(rC)-oligo(dG) at 0.1 uM
AID1470586	Antioxidant activity assessed as DPPH free radical scavenging activity at 12.5 ppm after 30 mins in dark by spectrophotometric method relative to control	2017	European journal of medicinal chemistry, May-26, Volume: 132	Recent synthetic and medicinal perspectives of dihydropyrimidinones: A review.
AID1197637	Antiviral activity against vaccinia virus	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID377909	Antioxidant activity assessed as DPPH free radical scavenging activity	2000	Journal of natural products, Oct, Volume: 63, Issue:10	Urinary metabolites of gallic acid in rats and their radical-scavenging effects on 1,1-diphenyl-2-picrylhydrazyl radical.
AID462275	Inhibition of human CA5B by stopped-flow CO2 hydration assay	2010	Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6	Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids.
AID1311770	Antiinflammatory activity against LPS-stimulated mouse RAW264.7 cells assessed as NO levels at 25 umol/L by ELISA (Rvb = 0.95 +/- 0.052 umol/mL)	2016	Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15	Anti-inflammatory polyphenol constituents derived from Cissus pteroclada Hayata.
AID381917	Cytotoxicity against mouse L1210 cells after 48 hrs by MTT assay	2008	Bioorganic & medicinal chemistry, Apr-01, Volume: 16, Issue:7	Ester derivatives of gallic acid with potential toxicity toward L1210 leukemia cells.
AID1105376	Antioxidant activity assessed as DPPH free radical scavenging activity at 0.8 ug/mL after 20 min by UV-Vis spectrophotometric analysis	2013	European journal of medicinal chemistry, Jan, Volume: 59	Microwave synthesis, characterization and bio-efficacy evaluation of novel chalcone based 6-carbethoxy-2-cyclohexen-1-one and 2H-indazol-3-ol derivatives.
AID1674379	Antifungal activity against Cryptococcus neoformans JEC21 by CLSI protocol-based broth serial dilution method
AID1083171	Antifungal activity against Togninia minima SO21 assessed as susceptibility at 500 uM measured after 1 to 10 days	2012	Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48	Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID1083159	Antifungal activity against Diplodia mutila BRA08 assessed as growth inhibition measured after 1 to 10 days	2012	Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48	Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID1591480	Antioxidant activity assessed as DPPH radical scavenging activity at 100 uM preincubated for 5 mins followed by DPPH addition and measured after 30 mins by ultraviolet spectrophotometric analysis relative to control	2019	Bioorganic & medicinal chemistry, 07-15, Volume: 27, Issue:14	Naphthalene-triazolopyrimidine hybrid compounds as potential multifunctional anti-Alzheimer's agents.
AID1674378	Antifungal activity against Cryptococcus neoformans H99 by CLSI protocol-based broth serial dilution method
AID1630418	Increase in cleaved caspase3 level in human NCI-H1650 cells harboring EGFR-mutant at 30 and 60 uM by immunoblotting analysis	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID1064674	Antioxidant activity of the compound assessed as inhibition of ABTS radicals after 20 mins by spectrophotometric analysis	2014	Bioorganic & medicinal chemistry, Feb-01, Volume: 22, Issue:3	Synthesis, modelling and biological characterization of 3-substituted-1H-indoles as ligands of GluN2B-containing N-methyl-d-aspartate receptors.
AID1197638	Antiviral activity against vesicular stomatitis virus	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID1197640	Antiviral activity against RSV	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID1630415	Induction of apoptosis in human A549 cells harboring wild-type EGFR assessed as cell death at 30 and 60 uM measured after 24 hrs by Annexin-V/PI staining based analysis	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID1161574	Antioxidant activity assessed as DPPH free radical scavenging activity measured as trolox equivalent after 30 mins by spectrophotometry	2014	Bioorganic & medicinal chemistry, Oct-01, Volume: 22, Issue:19	Shogaol-huprine hybrids: dual antioxidant and anticholinesterase agents with β-amyloid and tau anti-aggregating properties.
AID730115	Antioxidant activity assessed as DPPH radical scavenging activity at 5.5 mM	2013	Bioorganic & medicinal chemistry, Feb-15, Volume: 21, Issue:4	N-(Phenoxyalkyl)amides as MT(1) and MT(2) ligands: antioxidant properties and inhibition of Ca(2+)/CaM-dependent kinase II.
AID462273	Inhibition of human CA4 by stopped-flow CO2 hydration assay	2010	Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6	Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids.
AID689851	Antioxidant activity assessed as superoxide dismutase-like activity by SOD-WST assay	2012	Journal of natural products, Oct-26, Volume: 75, Issue:10	Diarylheptanoid sulfates and related compounds from Myrica rubra bark.
AID1310996	Cytotoxicity against human A549 cells assessed as reduction in cell viability measured after 48 hrs by luminescence-based ATP assay	2016	European journal of medicinal chemistry, Aug-25, Volume: 119	On the vasoprotective mechanisms underlying novel β-phosphorylated nitrones: Focus on free radical characterization, scavenging and NO-donation in a biological model of oxidative stress.
AID1337772	Cytoprotective activity against H2O2-induced oxidative stress in rat PC12 cells assessed as late apoptotic cells at 10 uM pretreated for 0.5 hrs followed by H2O2 challenge measured after 2 hrs by Annexin-V-FITC/propidium iodide staining based flow cytomet	2017	European journal of medicinal chemistry, Jan-05, Volume: 125	Synthesis and antioxidant evaluation of desmethylxanthohumol analogs and their dimers.
AID1128675	Cytotoxicity against mouse TA3/Ha cells after 48 hrs by neutral red assay	2014	Journal of medicinal chemistry, Mar-27, Volume: 57, Issue:6	Antiproliferative and uncoupling effects of delocalized, lipophilic, cationic gallic acid derivatives on cancer cell lines. Validation in vivo in singenic mice.
AID269889	DPPH radical scavenging activity in ethanol solution	2006	Bioorganic & medicinal chemistry letters, Aug-01, Volume: 16, Issue:15	Proton dissociation is important to understanding structure-activity relationships of gallic acid antioxidants.
AID1337778	Antioxidant activity assessed as ABTS radical scavenging activity measured after 10 mins by ABTS assay	2017	European journal of medicinal chemistry, Jan-05, Volume: 125	Synthesis and antioxidant evaluation of desmethylxanthohumol analogs and their dimers.
AID1082360	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 1% under light conditions measured 24 hr post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID1470594	Antioxidant activity assessed as cupric ion reducing activity by measuring increase in absorbance at 100 ppm by CUPRAC assay	2017	European journal of medicinal chemistry, May-26, Volume: 132	Recent synthetic and medicinal perspectives of dihydropyrimidinones: A review.
AID344828	Inhibition of NADPH oxidase in LPS-induced mouse BV2 cells assessed as NOX-dependent ROS production at 50 uM	2008	Bioorganic & medicinal chemistry, Nov-15, Volume: 16, Issue:22	New diterpenoids and the bioactivity of Erythrophleum fordii.
AID614104	Antimicrobial activity against Escherichia coli ATCC 11229 after 24 hrs using thiazoyl blue by agar overlay bioautography method	2011	Bioorganic & medicinal chemistry, Sep-01, Volume: 19, Issue:17	Tylosema esculentum extractives and their bioactivity.
AID1083157	Antifungal activity against Lasiodiplodia theobromae CBS116460 assessed as growth inhibition measured after 1 to 10 days	2012	Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48	Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID397157	Antioxidant activity against AAPH-induced lipid peroxidation in human plasma LDL at 0.2 umol/L preincubated for 1 hr before AAPH challenge	2001	Journal of natural products, Apr, Volume: 64, Issue:4	Specific antioxidant activity of caffeoyl derivatives and other natural phenolic compounds: LDL protection against oxidation and decrease in the proinflammatory lysophosphatidylcholine production.
AID1310998	Cytotoxicity against BAEC assessed as reduction in cell viability measured after 24 hrs by MTT assay	2016	European journal of medicinal chemistry, Aug-25, Volume: 119	On the vasoprotective mechanisms underlying novel β-phosphorylated nitrones: Focus on free radical characterization, scavenging and NO-donation in a biological model of oxidative stress.
AID339009	Cytotoxicity against mouse P388 cells
AID1187073	Inhibition of insulin fibril formation (unknown origin) assessed as secondary structural changes at 1:5 insulin to compound ratio at pH2 up to 12 hrs by Far-UV CD spectra	2014	European journal of medicinal chemistry, Oct-06, Volume: 85	Gallic acid, one of the components in many plant tissues, is a potential inhibitor for insulin amyloid fibril formation.
AID1494599	Anticomplement activity in sheep erythrocytes assessed as concentration required for 50% hemolytic inhibition by classic pathway pretreated for 10 mins with guinea pig serum followed by erythrocyte addition measured after 30 mins by spectrophotometeric me	2018	Bioorganic & medicinal chemistry letters, 05-15, Volume: 28, Issue:9	Anticomplement compounds from Polygonum chinense.
AID388742	Inhibition of cataracted human eye lens aldose reductase	2008	Bioorganic & medicinal chemistry, Dec-01, Volume: 16, Issue:23	Inhibition of aldose reductase from cataracted eye lenses by finger millet (Eleusine coracana) polyphenols.
AID1110806	Inhibition of xanthine oxidase assessed as conversion of xanthine to uric acid incubated for 3 min	2005	Phytochemistry, Jan, Volume: 66, Issue:2	Bioactive ellagitannins from Cunonia macrophylla, an endemic Cunoniaceae from New Caledonia.
AID1311774	Antiinflammatory activity against LPS-stimulated mouse RAW264.7 cells assessed as iNOS levels at 50 umol/L by ELISA (Rvb = 31.63 +/- 3.26 U/mL)	2016	Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15	Anti-inflammatory polyphenol constituents derived from Cissus pteroclada Hayata.
AID448520	Toxicity against Artemia salina assessed as number of the nauplii died after 24 hrs	2009	European journal of medicinal chemistry, Nov, Volume: 44, Issue:11	Synthesis of some novel pyrazolo[3,4-b]pyridine and pyrazolo[3,4-d]pyrimidine derivatives bearing 5,6-diphenyl-1,2,4-triazine moiety as potential antimicrobial agents.
AID1187071	Inhibition of insulin fibril formation (unknown origin) assessed as decrease in ThT fluorescence at 1:5 insulin to compound ratio at pH2 up to 12 hrs by ThT binding assay	2014	European journal of medicinal chemistry, Oct-06, Volume: 85	Gallic acid, one of the components in many plant tissues, is a potential inhibitor for insulin amyloid fibril formation.
AID400993	Inhibition of AMV reverse transcriptase activity assessed as incorporation of dGMP in poly(rC)-oligo(dG) at 1000 uM
AID1873809	Inhibition of amyloid beta 1 to 42 aggregation (unknown origin) incubated for 24 hrs by inverted fluorescence microscopic analysis	2022	Bioorganic & medicinal chemistry, 08-15, Volume: 68	Chemical analysis of amyloid β aggregation inhibitors derived from Geranium thunbergii.
AID377794	Antiplasmodial activity against chloroquine-susceptible Plasmodium falciparum FCR3 in human erythrocytes after 24 hrs	2005	Journal of natural products, Apr, Volume: 68, Issue:4	Anti-babesial and anti-plasmodial compounds from Phyllanthus niruri.
AID1630452	Induction of EGFR turnover in human NCI-H1975 cells harboring EGFR-mutant assessed as receptor half life prolongation at 60 uM in presence of cycloheximide by immunoblotting analysis	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID397104	Inhibition of Rauscher murine leukemia virus reverse transcriptase assessed as incorporation of [3H]dTMP at 10 ug/ml
AID1082351	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 0.5% under dark conditions measured 24 hr post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID1197648	Antiviral activity against feline herpesvirus	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID397156	Antioxidant activity against Cu2+-induced lipid peroxidation in human plasma LDL at 1 umol/L preincubated for 1 hr before Cu2+ challenge	2001	Journal of natural products, Apr, Volume: 64, Issue:4	Specific antioxidant activity of caffeoyl derivatives and other natural phenolic compounds: LDL protection against oxidation and decrease in the proinflammatory lysophosphatidylcholine production.
AID462278	Inhibition of human CA9 by stopped-flow CO2 hydration assay	2010	Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6	Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids.
AID707113	Inhibition of LPS-induced NO production in mouse RAW264.7 cells assessed as reduction in nitrite level within 24 hrs by Griess reagent method	2012	Journal of natural products, May-25, Volume: 75, Issue:5	Inhibition of NF-κB-dependent cytokine and inducible nitric oxide synthesis by the macrocyclic ellagitannin oenothein B in TLR-stimulated RAW 264.7 macrophages.
AID315609	Growth inhibition of human BGC823 cells at 100 uM after 72 hrs by MTT assay relative to control	2008	Bioorganic & medicinal chemistry, Feb-01, Volume: 16, Issue:3	Studies on the chemical constituents and anticancer activity of Saxifraga stolonifera (L) Meeb.
AID417968	Antimicrobial activity against Trichophyton rubrum after 48 hrs by broth microdilution technique	2009	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 19, Issue:6	Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi.
AID417961	Antifungal activity against Saccharomyces cerevisiae after 48 hrs by broth microdilution technique	2009	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 19, Issue:6	Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi.
AID614100	Antimicrobial activity against Staphylococcus aureus ATCC 9144 after 24 hrs using thiazoyl blue by agar overlay bioautography method	2011	Bioorganic & medicinal chemistry, Sep-01, Volume: 19, Issue:17	Tylosema esculentum extractives and their bioactivity.
AID548182	Antioxidant activity assessed as ABTS radical scavenging activity	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Benzophenones and biflavonoids from Rheedia edulis.
AID638442	Inhibition of yeast alpha-glucosidase using p-nitrophenyl-alpha-D-glucopyranoside as substrate preincubated for 10 mins before substrate addition measured after 5 mins by micro-plate reader analysis	2012	Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1	Maplexins, new α-glucosidase inhibitors from red maple (Acer rubrum) stems.
AID1055130	Inhibition of amyloid beta (1 to 40) (unknown origin) aggregation at 1:0.1 to 1:2 protein to compound molar ratio up to 10 hrs by thioflavin T fluorescence assay	2013	Bioorganic & medicinal chemistry letters, Dec-01, Volume: 23, Issue:23	Gallic acid is the major component of grape seed extract that inhibits amyloid fibril formation.
AID436175	Antiinflammatory activity in human neutrophils assessed as respiratory burst inhibition at 1000 ug/ml by WST-1 assay	2008	Journal of natural products, Nov, Volume: 71, Issue:11	Inhibitory effect of macabarterin, a polyoxygenated ellagitannin from Macaranga barteri, on human neutrophil respiratory burst activity.
AID400985	Inhibition of AMV reverse transcriptase activity assessed as incorporation of dTMP in poly(rA)-oligo(dT) at 1 uM
AID1479538	Antioxidant activity assessed as DPPH radical scavenging activity incubated in dark for 20 mins	2018	Journal of medicinal chemistry, 02-22, Volume: 61, Issue:4	The Synthesized Plant Metabolite 3,4,5-Tri-O-Galloylquinic Acid Methyl Ester Inhibits Calcium Oxalate Crystal Growth in a Drosophila Model, Downregulates Renal Cell Surface Annexin A1 Expression, and Decreases Crystal Adhesion to Cells.
AID1082341	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 0.125% under light conditions measured 5 to 60 min post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID400988	Inhibition of AMV reverse transcriptase activity assessed as incorporation of dTMP in poly(rA)-oligo(dT) at 1000 uM
AID1424229	Electrochemical behaviour of the compound assessed as peak potential	2017	European journal of medicinal chemistry, Jun-16, Volume: 133	Free radicals and polyphenols: The redox chemistry of neurodegenerative diseases.
AID691435	Inhibition of porcine pancreatic lipase using micellar solution of triolein as substrate at 1 mM preincubated for 5 mins before substrate addition measured after 30 mins	2012	Bioorganic & medicinal chemistry letters, Oct-15, Volume: 22, Issue:20	Substrate-like water soluble lipase inhibitors from Filipendula kamtschatica.
AID1311764	Antiinflammatory activity against LPS-stimulated mouse RAW264.7 cells assessed as IL1beta levels at 25 umol/L by ELISA (Rvb = 8.70 +/- 0.365 pg/mL)	2016	Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15	Anti-inflammatory polyphenol constituents derived from Cissus pteroclada Hayata.
AID711625	Increase of lifespan of L4 larvae of Caenorhabditis elegans after 8 hrs	2011	Journal of natural products, Aug-26, Volume: 74, Issue:8	Diversity of polyphenol action in Caenorhabditis elegans: between toxicity and longevity.
AID555372	Induction of toxin TSST-1 production in Staphylococcus aureus MN8 at 0.50 % after 24 hrs relative to control	2009	Antimicrobial agents and chemotherapy, May, Volume: 53, Issue:5	Surfactants, aromatic and isoprenoid compounds, and fatty acid biosynthesis inhibitors suppress Staphylococcus aureus production of toxic shock syndrome toxin 1.
AID732039	Antimigratory activity against human U87 cells at 30 ug/ml after 8 hrs by wound closure assay	2013	European journal of medicinal chemistry, Feb, Volume: 60	Alkyl esters of gallic acid as anticancer agents: a review.
AID1055140	Inhibition of reduced carboxymethylated-kappa-casein (unknown origin) conversion to amyloid fibrils after 1000 mins by thioflavin T fluorescence assay	2013	Bioorganic & medicinal chemistry letters, Dec-01, Volume: 23, Issue:23	Gallic acid is the major component of grape seed extract that inhibits amyloid fibril formation.
AID671764	Inhibition of HCV NS3 helicase ATP hydrolysis activity overexpressed in Escherichia coli BL21(DE3) assessed as inhibition of inorganic phosphate release by AM/MG-based colometric analysis in the presence of M13 ssDNA	2012	Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12	Identification of myricetin and scutellarein as novel chemical inhibitors of the SARS coronavirus helicase, nsP13.
AID86649	Percent reduction in cell viability of HeLa cells 72 hr after incubation with compound	2003	Journal of medicinal chemistry, Dec-04, Volume: 46, Issue:25	Anticancer activity of phenolic acids of natural or synthetic origin: a structure-activity study.
AID1759523	Antioxidant activity assessed as reduction in FK506-induced ROS production by DPPH assay	2021	Bioorganic & medicinal chemistry letters, 06-01, Volume: 41	Identification of gallic acid as a active ingredient of Syzygium aromaticum against tacrolimus-induced damage in renal epithelial LLC-PK1 cells and rat kidney.
AID397105	Inhibition of HIV reverse transcriptase expressed in Escherichia coli assessed as incorporation of [3H]dTMP at 10 ug/ml
AID732051	Cytotoxicity against human K562 cells	2013	European journal of medicinal chemistry, Feb, Volume: 60	Alkyl esters of gallic acid as anticancer agents: a review.
AID1310991	Antioxidant activity assessed as AAPH free radical scavenging activity measured as trolox equivalent by TRAP assay	2016	European journal of medicinal chemistry, Aug-25, Volume: 119	On the vasoprotective mechanisms underlying novel β-phosphorylated nitrones: Focus on free radical characterization, scavenging and NO-donation in a biological model of oxidative stress.
AID1630431	Inhibition of EGFR mutant-mediated ERK phosphorylation in human NCI-H1975 cells harboring EGFR-mutant at 30 and 60 uM measured after 24 hrs by immunoblotting analysis	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID1310997	Cytotoxicity against human A549 cells assessed as reduction in cell viability measured after 48 hrs by MTT assay	2016	European journal of medicinal chemistry, Aug-25, Volume: 119	On the vasoprotective mechanisms underlying novel β-phosphorylated nitrones: Focus on free radical characterization, scavenging and NO-donation in a biological model of oxidative stress.
AID1588067	Binding affinity of human recombinant FLAG-tagged ppGalNAcT2 expressed in HEK293 cells assessed as dissociation constant by SPR analysis	2019	Bioorganic & medicinal chemistry, 08-01, Volume: 27, Issue:15	Inhibition of polypeptide N-acetyl-α-galactosaminyltransferases is an underlying mechanism of dietary polyphenols preventing colorectal tumorigenesis.
AID1311777	Inhibition of NFkappaB signaling pathway in LPS-stimulated mouse RAW264.7 cells assessed as protein levels at 50umol/L by ELISA (Rvb = 1.23 +/- 0.06 pg/mL)	2016	Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15	Anti-inflammatory polyphenol constituents derived from Cissus pteroclada Hayata.
AID1110807	Antimicrobial activity against Candida albicans at 100 ug after 24 hr by disk diffusion method	2005	Phytochemistry, Jan, Volume: 66, Issue:2	Bioactive ellagitannins from Cunonia macrophylla, an endemic Cunoniaceae from New Caledonia.
AID475260	Antioxidant activity assessed as DPPH free radical scavenging activity at 1 uM after 2 mins by spectrophotometry	2010	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 20, Issue:7	Synthesis and biological evaluation of nitrogen-containing benzophenone analogues as TNF-alpha and IL-6 inhibitors with antioxidant activity.
AID1105372	Antioxidant activity assessed as DPPH free radical scavenging activity at 2 ug/mL after 20 min by UV-Vis spectrophotometric analysis	2013	European journal of medicinal chemistry, Jan, Volume: 59	Microwave synthesis, characterization and bio-efficacy evaluation of novel chalcone based 6-carbethoxy-2-cyclohexen-1-one and 2H-indazol-3-ol derivatives.
AID1891161	Inhibition of alpha-glycosidase (unknown origin) using pre-mix of compound and enzyme for 10 mins and then followed by maltose substrate addition and further incubated for 10 mins by microplate reader analysis	2022	Bioorganic & medicinal chemistry letters, 06-01, Volume: 65	Polyphenolic compounds: Synthesis, assessment of antimicrobial effect and enzymes inhibition against important medicinal enzymes with computational details.
AID732049	Cytotoxicity against human imatinib-resistant K562 cells	2013	European journal of medicinal chemistry, Feb, Volume: 60	Alkyl esters of gallic acid as anticancer agents: a review.
AID977602	Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	2013	Molecular pharmacology, Jun, Volume: 83, Issue:6	Structure-based identification of OATP1B1/3 inhibitors.
AID280293	Inhibition of human L-selectin after 2 hrs	2007	Journal of medicinal chemistry, Mar-22, Volume: 50, Issue:6	Rational design of novel, potent small molecule pan-selectin antagonists.
AID1490877	Induction of H2O2-inactivated bovine milk lactoperoxidase pseudo-halogenating activity assessed as increase in hypothiocyanate formation by measuring substrate Kcat using thiocyanate as substrate by Lineweaver-Burk plot	2017	Journal of natural products, 05-26, Volume: 80, Issue:5	Tannins and Tannin-Related Derivatives Enhance the (Pseudo-)Halogenating Activity of Lactoperoxidase.
AID732056	Cytotoxicity against human P388D1 cells	2013	European journal of medicinal chemistry, Feb, Volume: 60	Alkyl esters of gallic acid as anticancer agents: a review.
AID395150	ABTS radical scavenging activity assessed as Trolox equivalent antioxidant capacity	2009	European journal of medicinal chemistry, Jan, Volume: 44, Issue:1	QSAR study of antioxidant activity of wine polyphenols.
AID314590	Growth inhibition of Vibrio harveyi assessed as time required to double bacterial growth relative to control	2008	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 18, Issue:5	Pyrogallol and its analogs can antagonize bacterial quorum sensing in Vibrio harveyi.
AID377793	Antibabesial activity against Babesia gibsoni in dog erythrocytes after 72 hrs	2005	Journal of natural products, Apr, Volume: 68, Issue:4	Anti-babesial and anti-plasmodial compounds from Phyllanthus niruri.
AID1130099	Inhibition of human aromatase using androstenedione as substrate assessed as remaining estrone level at 10 uM after 30 mins by LC-MS/MS analysis relative to control	2014	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 24, Issue:7	Inhibitory effect of Rhus verniciflua Stokes extract on human aromatase activity; butin is its major bioactive component.
AID732042	Inhibition of ADAM17 alpha-secretase activity in human UI87 cells using amyloid beta precursor protein as substrate at 20 ug/ml after 24 hrs by fluorimetric analysis	2013	European journal of medicinal chemistry, Feb, Volume: 60	Alkyl esters of gallic acid as anticancer agents: a review.
AID380373	DPPH radical scavenging activity at 40 uM after 30 mins by spectrophotometric assay	2000	Journal of natural products, Jun, Volume: 63, Issue:6	Galloylglucosides from berries of Pimenta dioica.
AID1762120	Cytotoxicity against human ER-positive MCF7 cells assessed as increase in cell proliferation at 12.5 to 100 uM incubated for 24 hrs	2021	Bioorganic & medicinal chemistry letters, 05-15, Volume: 40	Estrogenic activity of ethyl gallate and its potential use in hormone replacement therapy.
AID1479527	Inhibition of calcium oxalate monohydrate crystal binding to MDCK1 cell surface at 10 uM preincubated for 3 hrs followed by calcium oxalate monohydrate crystal addition measured after 30 mins by phase contrast microscopy	2018	Journal of medicinal chemistry, 02-22, Volume: 61, Issue:4	The Synthesized Plant Metabolite 3,4,5-Tri-O-Galloylquinic Acid Methyl Ester Inhibits Calcium Oxalate Crystal Growth in a Drosophila Model, Downregulates Renal Cell Surface Annexin A1 Expression, and Decreases Crystal Adhesion to Cells.
AID1630450	Increase in PARP level in human gefitinib-resistant PC9 cells harboring EGFR T790M mutant at 30 and 60 uM by immunoblotting analysis	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID1630443	Antiproliferative activity against human erlotinib-resistant PC9 cells harboring EGFR T790M mutant assessed as cell viability measured after 24 hrs	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID381929	Induction of apoptosis in mouse L1210 cells assessed as internucleosomal breakdown of DNA chromatin at 100 uM	2008	Bioorganic & medicinal chemistry, Apr-01, Volume: 16, Issue:7	Ester derivatives of gallic acid with potential toxicity toward L1210 leukemia cells.
AID400986	Inhibition of AMV reverse transcriptase activity assessed as incorporation of dTMP in poly(rA)-oligo(dT) at 10 uM
AID1399450	Induction of apoptosis in human A549 cells assessed as necrotic cells at 2.5 uM after 48 hrs by Annexin-V-FITC/propidium iodide staining based flow cytometry (Rvb = 5.45%)	2018	Bioorganic & medicinal chemistry, 08-15, Volume: 26, Issue:15	Anti-angiogenic and anticancer effects of baicalein derivatives based on transgenic zebrafish model.
AID1479531	Cytotoxicity against MDCK1 cells assessed as decrease in cell viability after 24 hrs by MTT assay	2018	Journal of medicinal chemistry, 02-22, Volume: 61, Issue:4	The Synthesized Plant Metabolite 3,4,5-Tri-O-Galloylquinic Acid Methyl Ester Inhibits Calcium Oxalate Crystal Growth in a Drosophila Model, Downregulates Renal Cell Surface Annexin A1 Expression, and Decreases Crystal Adhesion to Cells.
AID711596	Increase of lifespan of Caenorhabditis elegans assessed as trolox equivalent of lipid soluble antioxidant metabolites at 300 uM by photochemiluminescence assay	2011	Journal of natural products, Aug-26, Volume: 74, Issue:8	Diversity of polyphenol action in Caenorhabditis elegans: between toxicity and longevity.
AID1055136	Inhibition of reduced carboxymethylated-kappa-casein (unknown origin) conversion to amyloid fibrils assessed as decrease in number of long, unbranched and mature amyloid fibrils at 1:2 protein to compound molar ratio after 1000 mins by transmission electr	2013	Bioorganic & medicinal chemistry letters, Dec-01, Volume: 23, Issue:23	Gallic acid is the major component of grape seed extract that inhibits amyloid fibril formation.
AID1465954	Inhibition of SPI-1 T3SS in Salmonella typhimurium expressing SopE2-CPG2-HA fusion protein assessed as reduction in type 3 protein secretion using Glu-CyFur as substrate at 25 uM after 4 hrs by fluorescence assay	2017	Bioorganic & medicinal chemistry, 06-01, Volume: 25, Issue:11	Epigallocatechin-3-gallate inhibits bacterial virulence and invasion of host cells.
AID1399449	Induction of apoptosis in human A549 cells assessed as late apoptotic cells at 2.5 uM after 48 hrs by Annexin-V-FITC/propidium iodide staining based flow cytometry (Rvb = 4.05%)	2018	Bioorganic & medicinal chemistry, 08-15, Volume: 26, Issue:15	Anti-angiogenic and anticancer effects of baicalein derivatives based on transgenic zebrafish model.
AID1630446	Decrease in EGFR level in human gefitinib-resistant PC9 cells harboring EGFR T790M mutant at 30 and 60 uM measured after 24 hrs by immunoblotting analysis	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID1337770	Cytoprotective activity against H2O2-induced oxidative stress in rat PC12 cells assessed as viable cells at 10 uM pretreated for 0.5 hrs followed by H2O2 challenge measured after 2 hrs by Annexin-V-FITC/propidium iodide staining based flow cytometry (Rvb	2017	European journal of medicinal chemistry, Jan-05, Volume: 125	Synthesis and antioxidant evaluation of desmethylxanthohumol analogs and their dimers.
AID381919	Cytotoxicity against human CEM cells after 24 hrs by MTT assay	2008	Bioorganic & medicinal chemistry, Apr-01, Volume: 16, Issue:7	Ester derivatives of gallic acid with potential toxicity toward L1210 leukemia cells.
AID1630425	Effect on ROS level in human NCI-H1975 cells harboring EGFR-mutant at 60 uM	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID732547	Activation of Nrf2 in mouse RAW264.7 cells assessed as upregulation of HO1 protein expression at 50 uM after 6 hrs by Western blotting analysis	2013	Journal of medicinal chemistry, Feb-14, Volume: 56, Issue:3	A novel semisynthetic flavonoid 7-O-galloyltaxifolin upregulates heme oxygenase-1 in RAW264.7 cells via MAPK/Nrf2 pathway.
AID1630417	Increase in cleaved caspase3 level in human NCI-H1975 cells harboring EGFR-mutant at 30 and 60 uM by immunoblotting analysis	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID1873812	Inhibition of amyloid beta 1 to 42 aggregation (unknown origin) incubated for 24 hrs by ThT fluorescence assay relative to control	2022	Bioorganic & medicinal chemistry, 08-15, Volume: 68	Chemical analysis of amyloid β aggregation inhibitors derived from Geranium thunbergii.
AID710229	Antioxidant activity of the compound assessed as DHR radical scavenging activity at 10 uM by fluorescence assay	2012	Journal of medicinal chemistry, Dec-13, Volume: 55, Issue:23	Carbamate derivatives of indolines as cholinesterase inhibitors and antioxidants for the treatment of Alzheimer's disease.
AID475262	Antioxidant activity assessed as DPPH free radical scavenging activity at 1 uM after 6 mins by spectrophotometry	2010	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 20, Issue:7	Synthesis and biological evaluation of nitrogen-containing benzophenone analogues as TNF-alpha and IL-6 inhibitors with antioxidant activity.
AID715002	Inhibition of mushroom tyrosinase using L-DOPA as substrate at 100 ug/ml after 10 mins	2012	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 22, Issue:17	Design, synthesis and molecular simulation studies of dihydrostilbene derivatives as potent tyrosinase inhibitors.
AID555341	Effect on growth in Staphylococcus aureus MN8 at 0.10 % after 24 hrs (Rvb = 100%)	2009	Antimicrobial agents and chemotherapy, May, Volume: 53, Issue:5	Surfactants, aromatic and isoprenoid compounds, and fatty acid biosynthesis inhibitors suppress Staphylococcus aureus production of toxic shock syndrome toxin 1.
AID1630410	Antiproliferative activity against human NCI-H1650 cells harboring EGFR-mutant assessed as cell viability measured after 24 hrs	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID725981	Inhibition of CMG2 (40 to 217) C175A and R40C double mutant (unknown origin) interaction to full length PA E733C mutant expressed in Escherichia coli by FRET assay	2013	Journal of medicinal chemistry, Mar-14, Volume: 56, Issue:5	1,2,3,4,6-Penta-O-galloyl-β-D-glucopyranose inhibits angiogenesis via inhibition of capillary morphogenesis gene 2.
AID1187070	Inhibition of insulin fibril formation (unknown origin) assessed as turbidity at 1:20 insulin to compound ratio at pH2 up to 12 hrs by atomic force microscopy	2014	European journal of medicinal chemistry, Oct-06, Volume: 85	Gallic acid, one of the components in many plant tissues, is a potential inhibitor for insulin amyloid fibril formation.
AID1337773	Cytoprotective activity against H2O2-induced oxidative stress in rat PC12 cells assessed as necrotic cells at 10 uM pretreated for 0.5 hrs followed by H2O2 challenge measured after 2 hrs by Annexin-V-FITC/propidium iodide staining based flow cytometry (Rv	2017	European journal of medicinal chemistry, Jan-05, Volume: 125	Synthesis and antioxidant evaluation of desmethylxanthohumol analogs and their dimers.
AID380375	DPPH radical scavenging activity at 10 uM after 30 mins by spectrophotometric assay	2000	Journal of natural products, Jun, Volume: 63, Issue:6	Galloylglucosides from berries of Pimenta dioica.
AID1311758	Cytotoxicity against mouse RAW264.7 cells assessed as reduction in cell viability at 50 umol/L after 24 hrs by MTT assay	2016	Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15	Anti-inflammatory polyphenol constituents derived from Cissus pteroclada Hayata.
AID732037	Antimigratory activity against human U251 cells at 30 ug/ml after 8 hrs by wound closure assay	2013	European journal of medicinal chemistry, Feb, Volume: 60	Alkyl esters of gallic acid as anticancer agents: a review.
AID1082352	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 1% under dark conditions measured 24 hr post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID1630423	Increase in PARP level in human A549 cells harboring wild-type EGFR at 30 and 60 uM by immunoblotting analysis	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID462276	Inhibition of human CA6 by stopped-flow CO2 hydration assay	2010	Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6	Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids.
AID1630451	Increase in PARP level in human erlotinib-resistant PC9 cells harboring EGFR T790M mutant at 30 and 60 uM by immunoblotting analysis	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID1055129	Inhibition of amyloid beta (1 to 40) (unknown origin) aggregation at 1:0.1 to 1:2 protein to compound molar ratio after 20 hrs by transmission electron microscopic analysis	2013	Bioorganic & medicinal chemistry letters, Dec-01, Volume: 23, Issue:23	Gallic acid is the major component of grape seed extract that inhibits amyloid fibril formation.
AID1055134	Cytotoxicity against rat PC12 cells assessed as cell viability at 5 uM after 48 hrs by MTT assay	2013	Bioorganic & medicinal chemistry letters, Dec-01, Volume: 23, Issue:23	Gallic acid is the major component of grape seed extract that inhibits amyloid fibril formation.
AID1873347	Inhibition of non-enzymatic glycation in hemoglobin (unknown origin) by spectrophotometric analysis	2022	Bioorganic & medicinal chemistry letters, 08-01, Volume: 69	New pyrazole-tetrazole hybrid compounds as potent α-amylase and non-enzymatic glycation inhibitors.
AID1337768	Antioxidant activity against H2O2-induced oxidative stress in rat PC12 cells assessed as viable cells at 100 uM pretreated for 0.5 hrs followed by H2O2 challenge measured after 2 hrs by MTT assay (Rvb = 25.47%)	2017	European journal of medicinal chemistry, Jan-05, Volume: 125	Synthesis and antioxidant evaluation of desmethylxanthohumol analogs and their dimers.
AID1337774	Cytoprotective activity against H2O2-induced oxidative stress in rat PC12 cells assessed as lactate dehydrogenase release at 10 uM pretreated for 30 mins followed by H2O2 challenge measured after 2 hrs by spectrophotometric method (Rvb = 479.77 U/L)	2017	European journal of medicinal chemistry, Jan-05, Volume: 125	Synthesis and antioxidant evaluation of desmethylxanthohumol analogs and their dimers.
AID1592383	Antioxidant activity assessed as DPPH radical scavenging activity measured after 45 mins by UV-Visible spectrophotometric based assay
AID1631834	Antitrypanosomal activity against Trypanosoma brucei brucei Lister 427 bloodstream forms after 72 hrs by resazurin-based assay	2016	Journal of medicinal chemistry, 08-25, Volume: 59, Issue:16	Profiling of Flavonol Derivatives for the Development of Antitrypanosomatidic Drugs.
AID732043	Cytotoxicity against rat fibroblast cells	2013	European journal of medicinal chemistry, Feb, Volume: 60	Alkyl esters of gallic acid as anticancer agents: a review.
AID1311001	Potentiation of SNP-induced vasorelaxant activity in Sprague-Dawley rat endothelium-intact aortic rings assessed as reduction in L-phenylephrine hydrochloride-induced contraction at 200 uM relative to SNP	2016	European journal of medicinal chemistry, Aug-25, Volume: 119	On the vasoprotective mechanisms underlying novel β-phosphorylated nitrones: Focus on free radical characterization, scavenging and NO-donation in a biological model of oxidative stress.
AID377796	Cytotoxicity against human RBC	2005	Journal of natural products, Apr, Volume: 68, Issue:4	Anti-babesial and anti-plasmodial compounds from Phyllanthus niruri.
AID1630414	Induction of apoptosis in human NCI-H1650 cells harboring EGFR-mutant assessed as cell death measured after 24 hrs by Annexin-V/PI staining based analysis	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID711612	Increase of body length of L4 larvae of Caenorhabditis elegans at 300 uM by microscopic analysis	2011	Journal of natural products, Aug-26, Volume: 74, Issue:8	Diversity of polyphenol action in Caenorhabditis elegans: between toxicity and longevity.
AID1630429	Decrease in EGFR level in human NCI-H1975 cells harboring EGFR-mutant measured after 24 hrs by immunoblotting analysis	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID315607	Growth inhibition of human BGC823 cells at 10 uM after 72 hrs by MTT assay relative to control	2008	Bioorganic & medicinal chemistry, Feb-01, Volume: 16, Issue:3	Studies on the chemical constituents and anticancer activity of Saxifraga stolonifera (L) Meeb.
AID711600	Increase of median lifespan of L4 larvae of Caenorhabditis elegans harboring eat-2 (ad465) at 300 uM after 8 hrs	2011	Journal of natural products, Aug-26, Volume: 74, Issue:8	Diversity of polyphenol action in Caenorhabditis elegans: between toxicity and longevity.
AID671762	Inhibition of HCV NS3 helicase overexpressed in Escherichia coli BL21(DE3) assessed as inhibition of DNA unwinding activity at 10 uM by FRET assay	2012	Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12	Identification of myricetin and scutellarein as novel chemical inhibitors of the SARS coronavirus helicase, nsP13.
AID1197621	Antiviral activity against HIV2 ROD infected in human CEM cells assessed as reduction in virus-induced cytopathicity after 4 to 5 days by microscopy based syncytium cell formation assay	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID401336	Antioxidant activity assessed by superoxide anion scavenging assay	1996	Journal of natural products, Feb, Volume: 59, Issue:2	Natural polyphenols (vegetable tannins) as drugs: possible modes of action.
AID736486	Antioxidant activity assessed as inhibition of ABTS radical formation for 15 mins by spectrophotometric analysis	2013	European journal of medicinal chemistry, Apr, Volume: 62	Exploring nature profits: development of novel and potent lipophilic antioxidants based on galloyl-cinnamic hybrids.
AID1705581	Cytoprotective activity against H2O2-induced cell death in human PC-12 cells assessed as cell viability at 30 to 100 uM incubated for 0.5 hrs followed by H2O2 stimulation and measured after 2 hrs by MTT assay	2020	European journal of medicinal chemistry, Dec-01, Volume: 207	Preparation, characterization, antioxidant evaluation of new curcumin derivatives and effects of forming HSA-bound nanoparticles on the stability and activity.
AID486891	Antioxidant activity assessed as DPPH radical scavenging activity after 2 hrs	2010	Journal of natural products, Jun-25, Volume: 73, Issue:6	Dihydro-beta-agarofuran sesquiterpenes and pentacyclic triterpenoids from the root bark of Osyris lanceolata.
AID1310990	Antioxidant activity assessed as DPPH scavenging activity measured after 3 mins by spectrophotometric method	2016	European journal of medicinal chemistry, Aug-25, Volume: 119	On the vasoprotective mechanisms underlying novel β-phosphorylated nitrones: Focus on free radical characterization, scavenging and NO-donation in a biological model of oxidative stress.
AID691434	Inhibition of porcine pancreatic lipase using micellar solution of triolein as substrate preincubated for 5 mins before substrate addition measured after 30 mins	2012	Bioorganic & medicinal chemistry letters, Oct-15, Volume: 22, Issue:20	Substrate-like water soluble lipase inhibitors from Filipendula kamtschatica.
AID1083163	Antifungal activity against Botryosphaeria dothidea OGE14 assessed as growth inhibition measured after 1 to 10 days relative to control	2012	Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48	Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID1256912	Inhibition of human IDH1 R132H mutant expressed in IPTG-induced Escherichia coli BL21 cells assessed as oxidation of NADPH to NADP+ after 5 mins by spectrophotometry	2015	Bioorganic & medicinal chemistry letters, Dec-01, Volume: 25, Issue:23	Discovery of α-mangostin as a novel competitive inhibitor against mutant isocitrate dehydrogenase-1.
AID1186051	Retention time of the compound by UPLC analysis	2014	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 24, Issue:17	Phytochemical analysis and antileukemic activity of polyphenolic constituents of Toona sinensis.
AID1630434	Decrease in EGFR level in human A549 cells harboring wild-type EGFR at 30 and 60 uM measured after 24 hrs by immunoblotting analysis	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID781325	pKa (acid-base dissociation constant) as determined by Liao ref: J Chem Info Model 2009	2014	Pharmaceutical research, Apr, Volume: 31, Issue:4	Comparison of the accuracy of experimental and predicted pKa values of basic and acidic compounds.
AID355137	Antimicrobial activity against Streptococcus mutans Ingbritt by disk diffusion method	1996	Journal of natural products, Oct, Volume: 59, Issue:10	Compounds from Syzygium aromaticum possessing growth inhibitory activity against oral pathogens.
AID1311761	Antiinflammatory activity against LPS-stimulated mouse RAW264.7 cells assessed as TNFalpha levels at 25 umol/L by ELISA (Rvb = 183.21 +/- 5.36 pg/mL)	2016	Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15	Anti-inflammatory polyphenol constituents derived from Cissus pteroclada Hayata.
AID1630430	Inhibition of EGFR mutant-mediated AKT phosphorylation in human NCI-H1975 cells harboring EGFR-mutant at 30 and 60 uM measured after 24 hrs by immunoblotting analysis	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID1311771	Antiinflammatory activity against LPS-stimulated mouse RAW264.7 cells assessed as NO levels at 50 umol/L by ELISA (Rvb = 0.95 +/- 0.052 umol/mL)	2016	Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15	Anti-inflammatory polyphenol constituents derived from Cissus pteroclada Hayata.
AID732059	Cytotoxicity against rat dRLh-84 cells	2013	European journal of medicinal chemistry, Feb, Volume: 60	Alkyl esters of gallic acid as anticancer agents: a review.
AID732055	Cytotoxicity against human Calu6 cells	2013	European journal of medicinal chemistry, Feb, Volume: 60	Alkyl esters of gallic acid as anticancer agents: a review.
AID1594825	Antioxidant activity assessed as superoxide dismutase-like activity measured after 20 mins by WST-based assay	2019	Journal of natural products, 06-28, Volume: 82, Issue:6	Konamycins A and B and Rubromycins CA1 and CA2, Aromatic Polyketides from the Tunicate-Derived Streptomyces hyaluromycini MB-PO13
AID501209	Antiviral activity against HSV1 infected african green monkey Vero cells assessed as reduction of plaque formation after 3 days by using crystal violet stain	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	Phloroglucinol glycosides from the fresh fruits of Eucalyptus maideni.
AID1490878	Induction of H2O2-inactivated bovine milk lactoperoxidase pseudo-halogenating activity assessed as increase in hypothiocyanate formation by measuring ratio of Kcat to Km for substrate using thiocyanate as substrate by Lineweaver-Burk plot	2017	Journal of natural products, 05-26, Volume: 80, Issue:5	Tannins and Tannin-Related Derivatives Enhance the (Pseudo-)Halogenating Activity of Lactoperoxidase.
AID1630447	Decrease in EGFR level in human erlotinib-resistant PC9 cells harboring EGFR T790M mutant at 30 and 60 uM measured after 24 hrs by immunoblotting analysis	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID397117	Inhibition of Rauscher murine leukemia virus reverse transcriptase activity
AID1105377	Antioxidant activity assessed as DPPH free radical scavenging activity at 0.4 ug/mL after 20 min by UV-Vis spectrophotometric analysis	2013	European journal of medicinal chemistry, Jan, Volume: 59	Microwave synthesis, characterization and bio-efficacy evaluation of novel chalcone based 6-carbethoxy-2-cyclohexen-1-one and 2H-indazol-3-ol derivatives.
AID1630433	Inhibition of EGFR mutant-mediated ERK phosphorylation in human NCI-H1650 cells harboring EGFR-mutant measured after 24 hrs by immunoblotting analysis	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID1540298	Anti-inflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced nitric oxide production preincubated for 2 hrs followed by LPS stimulation and measured after 24 hrs by by Griess assay
AID1158457	Enhancement of GLUT4 translocation in rat L6 cells expressing pIRAP-mOrange cDNAs at 10 uM after 10 mins by fluorescence assay relative to control	2014	Bioorganic & medicinal chemistry letters, Jul-15, Volume: 24, Issue:14	Chemical constituents from Eucalyptus citriodora Hook leaves and their glucose transporter 4 translocation activities.
AID1759522	Cytoprotective activity against pig LLC-PK1 cells assessed as reduction in FK506-induced cytotoxicity incubated for 2 hrs followed by FK506 stimulation and measured after 24 hrs by MTT assay	2021	Bioorganic & medicinal chemistry letters, 06-01, Volume: 41	Identification of gallic acid as a active ingredient of Syzygium aromaticum against tacrolimus-induced damage in renal epithelial LLC-PK1 cells and rat kidney.
AID1633145	Inhibition of chymotrypsin-like activity of purified human 20S proteasome assessed as decrease in AMC hydrolysis using Suc-Leu-Leu-Val-Tyr-AMC as substrate incubated for 30 mins by fluorometric analysis	2019	European journal of medicinal chemistry, Apr-01, Volume: 167	Another look at phenolic compounds in cancer therapy the effect of polyphenols on ubiquitin-proteasome system.
AID1082358	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 0.25% under light conditions measured 24 hr post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID1082359	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 0.5% under light conditions measured 24 hr post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID1055135	Binding affinity to reduced carboxymethylated-kappa-casein (unknown origin) at 1:2 protein to compound molar ratio after 20 hrs by far-UV-CD spectroscopic analysis	2013	Bioorganic & medicinal chemistry letters, Dec-01, Volume: 23, Issue:23	Gallic acid is the major component of grape seed extract that inhibits amyloid fibril formation.
AID1197641	Antiviral activity against human parainfluenza virus 3	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID732046	Cytotoxicity against human KB cells	2013	European journal of medicinal chemistry, Feb, Volume: 60	Alkyl esters of gallic acid as anticancer agents: a review.
AID1083161	Antifungal activity against Neofusicoccum parvum PER20 assessed as growth inhibition measured after 1 to 10 days	2012	Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48	Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID763541	Antioxidant activity assessed as inhibition of ABTS free radical generation at 9 uM after 20 mins by UV spectrophotometric analysis relative to control	2013	Bioorganic & medicinal chemistry, Aug-01, Volume: 21, Issue:15	Indole derivatives as dual-effective agents for the treatment of neurodegenerative diseases: synthesis, biological evaluation, and molecular modeling studies.
AID1599994	Antagonist activity at TLR2 in mouse RAW264.7 cells assessed as PAM3CSK4-induced NO production measured after 24 hrs by Griess assay	2019	European journal of medicinal chemistry, Oct-01, Volume: 179	Structure-activity relationship study and biological evaluation of SAC-Garlic acid conjugates as novel anti-inflammatory agents.
AID264487	[1-3H]-2-deoxy-D-glucose uptake in 3T3 L1 adipocytes	2006	Journal of medicinal chemistry, May-04, Volume: 49, Issue:9	Synthesis and structure-activity relationship study of antidiabetic penta-O-galloyl-D-glucopyranose and its analogues.
AID1228617	Antioxidant activity assessed as hydroxy radical-scavenging activity	2015	Journal of natural products, May-22, Volume: 78, Issue:5	Anti-inflammatory Hydrolyzable Tannins from Myricaria bracteata.
AID1187069	Inhibition of insulin fibril formation (unknown origin) assessed as turbidity at pH2 up to 12 hrs by UV/vis spectrometry	2014	European journal of medicinal chemistry, Oct-06, Volume: 85	Gallic acid, one of the components in many plant tissues, is a potential inhibitor for insulin amyloid fibril formation.
AID1491526	Cytoprotective activity against H2O2-induced apoptosis in rat PC12 cells assessed as live cells at 100 uM preincubated for 0.5 hrs followed by H2O2 addition measured after 2 hrs by Annexin V-FITC/propidium iodide staining based flow cytometry (Rvb = 37.3%	2017	European journal of medicinal chemistry, Sep-29, Volume: 138	Synthesis and anti-oxidant activity evaluation of (±)-Anastatins A, B and their analogs.
AID381923	Decrease in cytoplasmic glutathione level in mouse L1210 cells at 100 uM	2008	Bioorganic & medicinal chemistry, Apr-01, Volume: 16, Issue:7	Ester derivatives of gallic acid with potential toxicity toward L1210 leukemia cells.
AID1105370	Antioxidant activity assessed as DPPH free radical scavenging activity at 5 ug/mL after 20 min by UV-Vis spectrophotometric analysis	2013	European journal of medicinal chemistry, Jan, Volume: 59	Microwave synthesis, characterization and bio-efficacy evaluation of novel chalcone based 6-carbethoxy-2-cyclohexen-1-one and 2H-indazol-3-ol derivatives.
AID711623	Toxicity in L4 larvae of Caenorhabditis elegans at 800 uM after 8 hrs	2011	Journal of natural products, Aug-26, Volume: 74, Issue:8	Diversity of polyphenol action in Caenorhabditis elegans: between toxicity and longevity.
AID417967	Antimicrobial activity against Epidermophyton floccosum after 48 hrs by broth microdilution technique	2009	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 19, Issue:6	Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi.
AID1082345	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 2% under light conditions measured 5 to 60 min post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID1630438	Inhibition of EGFR-mediated AKT phosphorylation in human NCI-H460 cells harboring wild-type EGFR at 30 and 60 uM measured after 24 hrs by immunoblotting analysis	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID1129833	Inhibition of Influenza A virus (A/RI/5+/1957(H2N2)) recombinant neuraminidase using MUNANA as substrate at 100 uM after 30 mins	2014	Bioorganic & medicinal chemistry, Apr-01, Volume: 22, Issue:7	Benzophenone C-glucosides and gallotannins from mango tree stem bark with broad-spectrum anti-viral activity.
AID1055133	Reduction in RCM-kappa-casein-induced cytotoxicity against rat PC12 cells after 48 hrs by MTT assay	2013	Bioorganic & medicinal chemistry letters, Dec-01, Volume: 23, Issue:23	Gallic acid is the major component of grape seed extract that inhibits amyloid fibril formation.
AID732061	Cytotoxicity against human HL60RG cells	2013	European journal of medicinal chemistry, Feb, Volume: 60	Alkyl esters of gallic acid as anticancer agents: a review.
AID1197644	Antiviral activity against influenza A virus H3N2	2015	European journal of medicinal chemistry, Mar-06, Volume: 92	Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID1485218	Antioxidant activity assessed as reduction in AAPH-induced DNA oxidation up to 400 uM measured every 2 hrs by TBARS assay	2017	European journal of medicinal chemistry, Jul-28, Volume: 135	2-Isocyano glucose used in Ugi four-component reaction: An approach to enhance inhibitory effect against DNA oxidation.
AID732057	Cytotoxicity against human HeLa cells	2013	European journal of medicinal chemistry, Feb, Volume: 60	Alkyl esters of gallic acid as anticancer agents: a review.
AID1128676	Cytotoxicity against mouse multidrug-resistant TA3-MTX-R cells after 48 hrs by neutral red assay	2014	Journal of medicinal chemistry, Mar-27, Volume: 57, Issue:6	Antiproliferative and uncoupling effects of delocalized, lipophilic, cationic gallic acid derivatives on cancer cell lines. Validation in vivo in singenic mice.
AID381927	Induction of apoptosis in mouse L1210 cells assessed as internucleosomal breakdown of DNA chromatin at 30 uM	2008	Bioorganic & medicinal chemistry, Apr-01, Volume: 16, Issue:7	Ester derivatives of gallic acid with potential toxicity toward L1210 leukemia cells.
AID1592384	Antioxidant activity assessed as ABTS radical scavenging activity measured after 15 mins by UV-Visible spectrophotometric based assay
AID1055138	Inhibition of reduced carboxymethylated-kappa-casein (unknown origin) conversion to amyloid fibrils at 1:0.5 protein to compound molar ratio after 1000 mins by thioflavin T fluorescence assay relative to control	2013	Bioorganic & medicinal chemistry letters, Dec-01, Volume: 23, Issue:23	Gallic acid is the major component of grape seed extract that inhibits amyloid fibril formation.
AID280289	Inhibition of human E-selectin after 2 hrs	2007	Journal of medicinal chemistry, Mar-22, Volume: 50, Issue:6	Rational design of novel, potent small molecule pan-selectin antagonists.
AID269890	DPPH radical scavenging activity in liposome	2006	Bioorganic & medicinal chemistry letters, Aug-01, Volume: 16, Issue:15	Proton dissociation is important to understanding structure-activity relationships of gallic acid antioxidants.
AID710231	Antioxidant activity assessed as scavenging of morpholino sydononimine based nitric oxide release by chemiluminescence assay	2012	Journal of medicinal chemistry, Dec-13, Volume: 55, Issue:23	Carbamate derivatives of indolines as cholinesterase inhibitors and antioxidants for the treatment of Alzheimer's disease.
AID614103	Antimicrobial activity against Candida albicans ATCC 10231 after 24 hrs using thiazoyl blue by agar overlay bioautography method	2011	Bioorganic & medicinal chemistry, Sep-01, Volume: 19, Issue:17	Tylosema esculentum extractives and their bioactivity.
AID1161573	Antioxidant activity assessed as ABTS free radical scavenging activity measured as trolox equivalent after 1 hr by spectrophotometry	2014	Bioorganic & medicinal chemistry, Oct-01, Volume: 22, Issue:19	Shogaol-huprine hybrids: dual antioxidant and anticholinesterase agents with β-amyloid and tau anti-aggregating properties.
AID1311769	Antiinflammatory activity against LPS-stimulated mouse RAW264.7 cells assessed as NO levels at 5 umol/L by ELISA (Rvb = 0.95 +/- 0.052 umol/mL)	2016	Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15	Anti-inflammatory polyphenol constituents derived from Cissus pteroclada Hayata.
AID1630432	Decrease in EGFR level in human NCI-H1650 cells harboring EGFR-mutant at 30 and 60 uM by RT-PCR method	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID1055141	Inhibition of reduced carboxymethylated-kappa-casein (unknown origin) conversion to amyloid fibrils at 1:2 protein to compound molar ratio after 1000 mins by thioflavin T fluorescence assay relative to control	2013	Bioorganic & medicinal chemistry letters, Dec-01, Volume: 23, Issue:23	Gallic acid is the major component of grape seed extract that inhibits amyloid fibril formation.
AID475023	Antioxidant activity assessed as DPPH free radical scavenging activity at 1 mM after 20 mins by spectrophotometry	2010	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 20, Issue:7	Synthesis and biological evaluation of nitrogen-containing benzophenone analogues as TNF-alpha and IL-6 inhibitors with antioxidant activity.
AID397586	Effect on human plasma LDL-PLA2 activity by LS-3B fluorescence spectrometry	2001	Journal of natural products, Apr, Volume: 64, Issue:4	Specific antioxidant activity of caffeoyl derivatives and other natural phenolic compounds: LDL protection against oxidation and decrease in the proinflammatory lysophosphatidylcholine production.
AID1083149	Nematotoxic activity against freshly hatched Meloidogyne incognita J2 (root-knot nematode) isolated from tomato roots assessed as induction of nematode paralysis measured 24 hr after immersion in compound test solutions	2012	Journal of agricultural and food chemistry, Nov-28, Volume: 60, Issue:47	Nematotoxic phenolic compounds from Melia azedarach against Meloidogyne incognita.
AID1630427	Induction of apoptosis in human NCI-H1975 cells harboring EGFR-mutant assessed as cell death at 60 uM in presence of NAC	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID344829	Inhibition of iNOS-mediated NO production in LPS-induced mouse BV2 cells	2008	Bioorganic & medicinal chemistry, Nov-15, Volume: 16, Issue:22	New diterpenoids and the bioactivity of Erythrophleum fordii.
AID1630419	Increase in cleaved caspase3 level in human A549 cells harboring wild-type EGFR at 30 and 60 uM by immunoblotting analysis	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID101828	Percent reduction in cell viability of MDA-MB-231 cells 72 hr after incubation with compound	2003	Journal of medicinal chemistry, Dec-04, Volume: 46, Issue:25	Anticancer activity of phenolic acids of natural or synthetic origin: a structure-activity study.
AID1083158	Antifungal activity against Diplodia seriata PLU03 assessed as growth inhibition measured after 1 to 10 days	2012	Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48	Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID1630435	Inhibition of EGFR-mediated AKT phosphorylation in human A549 cells harboring wild-type EGFR at 30 and 60 uM measured after 24 hrs by immunoblotting analysis	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID486890	Antioxidant activity assessed as DPPH radical scavenging activity after 30 mins	2010	Journal of natural products, Jun-25, Volume: 73, Issue:6	Dihydro-beta-agarofuran sesquiterpenes and pentacyclic triterpenoids from the root bark of Osyris lanceolata.
AID486892	Antioxidant activity assessed as DPPH radical scavenging activity after 8 hrs	2010	Journal of natural products, Jun-25, Volume: 73, Issue:6	Dihydro-beta-agarofuran sesquiterpenes and pentacyclic triterpenoids from the root bark of Osyris lanceolata.
AID397116	Inhibition of HIV reverse transcriptase activity expressed in Escherichia coli
AID475263	Antioxidant activity assessed as DPPH free radical scavenging activity at 1 uM after 8 mins by spectrophotometry	2010	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 20, Issue:7	Synthesis and biological evaluation of nitrogen-containing benzophenone analogues as TNF-alpha and IL-6 inhibitors with antioxidant activity.
AID1730561	Inhibition of Stenotrophomonas maltophilia SmltD using UDP-MurNAc-L-Ala-L-Glu as substrate in presence of ATP incubated for 5 mins by HPLC	2021	Bioorganic & medicinal chemistry letters, 03-15, Volume: 36	Flavonoids from Woodfordia fruticosa as potential SmltD inhibitors in the alternative biosynthetic pathway of peptidoglycan.
AID1082342	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 0.25% under light conditions measured 5 to 60 min post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID1191655	Antioxidant activity assessed as ABTS scavenging activity after 6 mins by spectrophotometry	2015	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 25, Issue:5	Schiff's bases of quinazolinone derivatives: Synthesis and SAR studies of a novel series of potential anti-inflammatory and antioxidants.
AID1630422	Increase in PARP level in human NCI-H1650 cells harboring EGFR-mutant at 30 and 60 uM by immunoblotting analysis	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID360324	Antiplasmodial activity after 24 hrs against chloroquine-sensitive, mefloquine-resistant Plasmodium falciparum D6 infected human erythrocytes by [G-3H]hypoxanthine uptake	2001	Journal of natural products, May, Volume: 64, Issue:5	In vitro antiplasmodial activity of extracts of Tristaniopsis species and identification of the active constituents: ellagic acid and 3,4,5-trimethoxyphenyl-(6'-O-galloyl)-O-beta-D-glucopyranoside.
AID1105374	Antioxidant activity assessed as DPPH free radical scavenging activity at 1 ug/mL after 20 min by UV-Vis spectrophotometric analysis	2013	European journal of medicinal chemistry, Jan, Volume: 59	Microwave synthesis, characterization and bio-efficacy evaluation of novel chalcone based 6-carbethoxy-2-cyclohexen-1-one and 2H-indazol-3-ol derivatives.
AID1311768	Antiinflammatory activity against LPS-stimulated mouse RAW264.7 cells assessed as PGE2 levels at 50 umol/L by ELISA (Rvb = 33.2 +/- 2.33 pg/mL)	2016	Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15	Anti-inflammatory polyphenol constituents derived from Cissus pteroclada Hayata.
AID1630444	Induction of apoptosis in human gefitinib-resistant PC9 cells harboring EGFR T790M mutant assessed as cell death at 30 and 60 uM measured after 24 hrs by Annexin-V/PI staining based analysis	2016	Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19	Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.
AID1296008	Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening	2020	SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1	Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346986	P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen	2019	Molecular pharmacology, 11, Volume: 96, Issue:5	A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346987	P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen	2019	Molecular pharmacology, 11, Volume: 96, Issue:5	A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347107	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh30 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347101	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-12 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347093	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-MC cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347407	qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS Pharmaceutical Collection	2020	ACS chemical biology, 07-17, Volume: 15, Issue:7	High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle.
AID1347089	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for TC32 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347100	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for LAN-5 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1508630	Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay	2021	Cell reports, 04-27, Volume: 35, Issue:4	A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347086	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347092	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for A673 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347083	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347104	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for RD cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1745845	Primary qHTS for Inhibitors of ATXN expression
AID1347097	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Saos-2 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347154	Primary screen GU AMC qHTS for Zika virus inhibitors	2020	Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49	Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347105	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for MG 63 (6-TG R) cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347102	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh18 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347091	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SJ-GBM2 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347095	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB-EBc1 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID651635	Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1347082	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347094	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-37 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347090	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for DAOY cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347424	RapidFire Mass Spectrometry qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)	2019	The Journal of biological chemistry, 11-15, Volume: 294, Issue:46	Physiologically relevant orthogonal assays for the discovery of small-molecule modulators of WIP1 phosphatase in high-throughput screens.
AID1347425	Rhodamine-PBP qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)	2019	The Journal of biological chemistry, 11-15, Volume: 294, Issue:46	Physiologically relevant orthogonal assays for the discovery of small-molecule modulators of WIP1 phosphatase in high-throughput screens.
AID1347108	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh41 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347103	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for OHS-50 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347099	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB1643 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347098	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-SH cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347096	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for U-2 OS cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347106	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for control Hh wild type fibroblast cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID504749	qHTS profiling for inhibitors of Plasmodium falciparum proliferation	2011	Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043	Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
AID588519	A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities	2011	Antiviral research, Sep, Volume: 91, Issue:3	High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID540299	A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis	2010	Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21	Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID1799773	SPA Assay from Article 10.1016/j.abb.2004.02.039: \\Inhibition of fucosyltransferase VII by gallic acid and its derivatives.\\	2004	Archives of biochemistry and biophysics, May-01, Volume: 425, Issue:1	Inhibition of fucosyltransferase VII by gallic acid and its derivatives.
AID1799774	TACE Inhibition Assay from Article 10.1016/j.abb.2004.02.039: \\Inhibition of fucosyltransferase VII by gallic acid and its derivatives.\\	2004	Archives of biochemistry and biophysics, May-01, Volume: 425, Issue:1	Inhibition of fucosyltransferase VII by gallic acid and its derivatives.
AID1799599	Esterase Activity Assay from Article 10.1111/j.1747-0285.2010.00965.x: \\Carbonic anhydrase inhibitors: Inhibition of human erythrocyte isozymes I and II with a series of phenolic acids.\\	2010	Chemical biology & drug design, May, Volume: 75, Issue:5	Carbonic anhydrase inhibitors: Inhibition of human erythrocyte isozymes I and II with a series of phenolic acids.
AID1799783	Enzymatic Assay from Article 10.1074/jbc.M109.067967: \\Characterization of a novel class of polyphenolic inhibitors of plasminogen activator inhibitor-1.\\	2010	The Journal of biological chemistry, Mar-12, Volume: 285, Issue:11	Characterization of a novel class of polyphenolic inhibitors of plasminogen activator inhibitor-1.
AID1799825	Inhibition Assay from Article : \\Partial identity of the 2-oxoglutarate and ascorbate binding sites of prolyl 4-hydroxylase.\\	1986	The Journal of biological chemistry, Jun-15, Volume: 261, Issue:17	Partial identity of the 2-oxoglutarate and ascorbate binding sites of prolyl 4-hydroxylase.
AID1159607	Screen for inhibitors of RMI FANCM (MM2) intereaction	2016	Journal of biomolecular screening, Jul, Volume: 21, Issue:6	A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
AID1345928	Human carbonic anhydrase 1 (4.2.1.1 Carbonate dehydratases)	2010	Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6	Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids.
AID1159550	Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening	2015	Nature cell biology, Nov, Volume: 17, Issue:11	6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	609 (13.25)	18.7374
1990's	431 (9.38)	18.2507
2000's	833 (18.13)	29.6817
2010's	1914 (41.65)	24.3611
2020's	808 (17.58)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	42 (0.88%)	5.53%
Reviews	99 (2.07%)	6.00%
Case Studies	31 (0.65%)	4.05%
Observational	1 (0.02%)	0.25%
Other	4,620 (96.39%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
2,3-dihydroxybenzoic acid 2,3-dihydroxybenzoic acid: RN given refers to parent cpd. dihydroxybenzoic acid : Any member of the class of hydroxybenzoic acids carrying two phenolic hydroxy groups on the benzene ring and its derivatives.. 2,3-dihydroxybenzoic acid : A dihydroxybenzoic acid that is benzoic acid substituted by hydroxy groups at positions 2 and 3. It occurs naturally in Phyllanthus acidus and in the aquatic fern Salvinia molesta.	4.39	6	0	dihydroxybenzoic acid	human xenobiotic metabolite; plant metabolite
protocatechuic acid protocatechuic acid: RN given refers to parent cpd; structure. 3,4-dihydroxybenzoic acid : A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4.	10.55	110	2	catechols; dihydroxybenzoic acid	antineoplastic agent; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor; human xenobiotic metabolite; plant metabolite
dihydro-3-coumaric acid dihydro-3-coumaric acid: intermediate in biosynthesis of dihydrophenanthrenes from phenylalanine. 3-(3-hydroxyphenyl)propanoic acid : A monocarboxylic acid that is propionic acid carrying a 3-hydroxyphenyl substituent at C-3.	3.87	2	1	monocarboxylic acid	Escherichia coli metabolite; human xenobiotic metabolite
3-phenylpropionic acid 3-phenylpropionic acid: RN given refers to parent cpd. 3-phenylpropionic acid : A monocarboxylic acid that is propionic acid substituted at position 3 by a phenyl group.	2.51	2	0	benzenes; monocarboxylic acid	antifungal agent; human metabolite; plant metabolite
cysteine sulfinic acid cysteine sulfinic acid: metabolite of sulfur-containing amino acids	2	1	0
gamma-aminobutyric acid gamma-Aminobutyric Acid: The most common inhibitory neurotransmitter in the central nervous system.. gamma-aminobutyric acid : A gamma-amino acid that is butanoic acid with the amino substituent located at C-4.	3.49	7	0	amino acid zwitterion; gamma-amino acid; monocarboxylic acid	human metabolite; neurotransmitter; Saccharomyces cerevisiae metabolite; signalling molecule
4-hydroxybenzyl alcohol 4-hydroxybenzyl alcohol: the aglycone of gastrodin. p-hydroxybenzyl alcohol : A member of the class of benzyl alcohols that is benzyl alcohol substituted by a hydroxy group at position 4. It has been isolated from Arcangelisia gusanlung.	2.31	1	0	benzyl alcohols; phenols	plant metabolite
4-hydroxybenzaldehyde [no description available]	2.45	2	0	hydroxybenzaldehyde	EC 1.14.17.1 (dopamine beta-monooxygenase) inhibitor; mouse metabolite; plant metabolite
4-hydroxyphenylacetic acid 4-hydroxyphenylacetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group.	5.08	3	1	monocarboxylic acid; phenols	fungal metabolite; human metabolite; mouse metabolite; plant metabolite
4-hydroxybenzoic acid 4-hydroxybenzoic acid : A monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring.	8.11	42	1	monohydroxybenzoic acid	algal metabolite; plant metabolite
ethylene glycol Ethylene Glycol: A colorless, odorless, viscous dihydroxy alcohol. It has a sweet taste, but is poisonous if ingested. Ethylene glycol is the most important glycol commercially available and is manufactured on a large scale in the United States. It is used as an antifreeze and coolant, in hydraulic fluids, and in the manufacture of low-freezing dynamites and resins.. ethanediol : Any diol that is ethane or substituted ethane carrying two hydroxy groups.. ethylene glycol : A 1,2-glycol compound produced via reaction of ethylene oxide with water.	2.54	2	0	ethanediol; glycol	metabolite; mouse metabolite; solvent; toxin
acetic acid Acetic Acid: Product of the oxidation of ethanol and of the destructive distillation of wood. It is used locally, occasionally internally, as a counterirritant and also as a reagent. (Stedman, 26th ed). acetic acid : A simple monocarboxylic acid containing two carbons.	3.67	9	0	monocarboxylic acid	antimicrobial food preservative; Daphnia magna metabolite; food acidity regulator; protic solvent
acetaldehyde Acetaldehyde: A colorless, flammable liquid used in the manufacture of acetic acid, perfumes, and flavors. It is also an intermediate in the metabolism of alcohol. It has a general narcotic action and also causes irritation of mucous membranes. Large doses may cause death from respiratory paralysis.. acetaldehyde : The aldehyde formed from acetic acid by reduction of the carboxy group. It is the most abundant carcinogen in tobacco smoke.. aldehyde : A compound RC(=O)H, in which a carbonyl group is bonded to one hydrogen atom and to one R group.. acetyl group : A group, formally derived from acetic acid by dehydroxylation, which is fundamental to the biochemistry of all forms of life. When bound to coenzyme A, it is central to the metabolism of carbohydrates and fats.	7.94	4	0	aldehyde	carcinogenic agent; EC 3.5.1.4 (amidase) inhibitor; electron acceptor; Escherichia coli metabolite; human metabolite; mouse metabolite; mutagen; oxidising agent; Saccharomyces cerevisiae metabolite; teratogenic agent
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	3.83	11	0	ketone body; methyl ketone; propanones; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; human metabolite; polar aprotic solvent
adenine [no description available]	7.68	3	0	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
adipic acid adipic acid : An alpha,omega-dicarboxylic acid that is the 1,4-dicarboxy derivative of butane.	2.13	1	0	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	food acidity regulator; human xenobiotic metabolite
allantoin [no description available]	2.08	1	0	imidazolidine-2,4-dione; ureas	Escherichia coli metabolite; human metabolite; Saccharomyces cerevisiae metabolite; vulnerary
ammonium hydroxide azane : Saturated acyclic nitrogen hydrides having the general formula NnHn+2.	3.04	3	0	azane; gas molecular entity; mononuclear parent hydride	EC 3.5.1.4 (amidase) inhibitor; metabolite; mouse metabolite; neurotoxin; NMR chemical shift reference compound; nucleophilic reagent; refrigerant
anthranilic acid anthranilic acid: RN given refers to parent cpd; structure in Negwer, 5th ed, #565. anthranilic acid : An aminobenzoic acid that is benzoic acid having a single amino substituent located at position 2. It is a metabolite produced in L-tryptophan-kynurenine pathway in the central nervous system.	2.73	3	0	aminobenzoic acid	human metabolite; mouse metabolite
quinacrine Quinacrine: An acridine derivative formerly widely used as an antimalarial but superseded by chloroquine in recent years. It has also been used as an anthelmintic and in the treatment of giardiasis and malignant effusions. It is used in cell biological experiments as an inhibitor of phospholipase A2.. quinacrine : A member of the class of acridines that is acridine substituted by a chloro group at position 6, a methoxy group at position 2 and a [5-(diethylamino)pentan-2-yl]nitrilo group at position 9.	3.08	5	0	acridines; aromatic ether; organochlorine compound; tertiary amino compound	antimalarial; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor
beta-alanine [no description available]	2.1	1	0	amino acid zwitterion; beta-amino acid	agonist; fundamental metabolite; human metabolite; inhibitor; neurotransmitter
benzaldehyde [no description available]	2.49	2	0	benzaldehydes	EC 3.1.1.3 (triacylglycerol lipase) inhibitor; EC 3.5.5.1 (nitrilase) inhibitor; flavouring agent; fragrance; odorant receptor agonist; plant metabolite
benzene [no description available]	2.8	3	0	aromatic annulene; benzenes; volatile organic compound	carcinogenic agent; environmental contaminant; non-polar solvent
benzoic acid Benzoic Acid: A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid.. benzoic acid : A compound comprising a benzene ring core carrying a carboxylic acid substituent.. aromatic carboxylic acid : Any carboxylic acid in which the carboxy group is directly bonded to an aromatic ring.	6.45	31	0	benzoic acids	algal metabolite; antimicrobial food preservative; drug allergen; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 3.1.1.3 (triacylglycerol lipase) inhibitor; human xenobiotic metabolite; plant metabolite
benzyl alcohol Benzyl Alcohol: A colorless liquid with a sharp burning taste and slight odor. It is used as a local anesthetic and to reduce pain associated with LIDOCAINE injection. Also, it is used in the manufacture of other benzyl compounds, as a pharmaceutic aid, and in perfumery and flavoring.. hydroxytoluene : Any member of the class of toluenes carrying one or more hydroxy substituents.. benzyl alcohol : An aromatic alcohol that consists of benzene bearing a single hydroxymethyl substituent.. aromatic alcohol : Any alcohol in which the alcoholic hydroxy group is attached to a carbon which is itself bonded to an aromatic ring.. aromatic primary alcohol : Any primary alcohol in which the alcoholic hydroxy group is attached to a carbon which is itself bonded to an aromatic ring.	3.52	2	0	benzyl alcohols	antioxidant; fragrance; metabolite; solvent
betaine glycine betaine : The amino acid betaine derived from glycine.	2.1	1	0	amino-acid betaine; glycine derivative	fundamental metabolite
bromide Bromides: Salts of hydrobromic acid, HBr, with the bromine atom in the 1- oxidation state. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	2.25	1	0	halide anion; monoatomic bromine
1-butanol 1-Butanol: A four carbon linear hydrocarbon that has a hydroxy group at position 1.. butan-1-ol : A primary alcohol that is butane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It it produced in small amounts in humans by the gut microbes.	4.51	5	1	alkyl alcohol; primary alcohol; short-chain primary fatty alcohol	human metabolite; mouse metabolite; protic solvent
butyric acid Butyric Acid: A four carbon acid, CH3CH2CH2COOH, with an unpleasant odor that occurs in butter and animal fat as the glycerol ester.. butyrate : A short-chain fatty acid anion that is the conjugate base of butyric acid, obtained by deprotonation of the carboxy group.. butyric acid : A straight-chain saturated fatty acid that is butane in which one of the terminal methyl groups has been oxidised to a carboxy group.	3.85	3	0	fatty acid 4:0; straight-chain saturated fatty acid	human urinary metabolite; Mycoplasma genitalium metabolite
carbamates [no description available]	2.4	2	0	amino-acid anion
carbon monoxide Carbon Monoxide: Carbon monoxide (CO). A poisonous colorless, odorless, tasteless gas. It combines with hemoglobin to form carboxyhemoglobin, which has no oxygen carrying capacity. The resultant oxygen deprivation causes headache, dizziness, decreased pulse and respiratory rates, unconsciousness, and death. (From Merck Index, 11th ed). carbon monoxide : A one-carbon compound in which the carbon is joined only to a single oxygen. It is a colourless, odourless, tasteless, toxic gas.	2.36	2	0	carbon oxide; gas molecular entity; one-carbon compound	biomarker; EC 1.9.3.1 (cytochrome c oxidase) inhibitor; human metabolite; ligand; metabolite; mitochondrial respiratory-chain inhibitor; mouse metabolite; neurotoxin; neurotransmitter; P450 inhibitor; probe; signalling molecule; vasodilator agent
formic acid formic acid: RN given refers to parent cpd. formic acid : The simplest carboxylic acid, containing a single carbon. Occurs naturally in various sources including the venom of bee and ant stings, and is a useful organic synthetic reagent. Principally used as a preservative and antibacterial agent in livestock feed. Induces severe metabolic acidosis and ocular injury in human subjects.	3.3	6	0	monocarboxylic acid	antibacterial agent; astringent; metabolite; protic solvent; solvent
carnitine [no description available]	1.97	1	0	amino-acid betaine	human metabolite; mouse metabolite
catechol [no description available]	4.65	27	0	catechols	allelochemical; genotoxin; plant metabolite
methane Methane: The simplest saturated hydrocarbon. It is a colorless, flammable gas, slightly soluble in water. It is one of the chief constituents of natural gas and is formed in the decomposition of organic matter. (Grant & Hackh's Chemical Dictionary, 5th ed). methane : A one-carbon compound in which the carbon is attached by single bonds to four hydrogen atoms. It is a colourless, odourless, non-toxic but flammable gas (b.p. -161degreeC).	9.07	13	0	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
choline [no description available]	3.51	8	0	cholines	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter; nutrient; plant metabolite; Saccharomyces cerevisiae metabolite
aconitic acid Aconitic Acid: A tricarboxylic acid with the formula (COOH)-CH2-C(COOH)=CH-COOH.. aconitic acid : A tricarboxylic acid that is prop-1-ene substituted by carboxy groups at positions 1, 2 and 3.	2.15	1	0	tricarboxylic acid
citric acid, anhydrous Citric Acid: A key intermediate in metabolism. It is an acid compound found in citrus fruits. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability.. citric acid : A tricarboxylic acid that is propane-1,2,3-tricarboxylic acid bearing a hydroxy substituent at position 2. It is an important metabolite in the pathway of all aerobic organisms.	5.61	13	0	tricarboxylic acid	antimicrobial agent; chelator; food acidity regulator; fundamental metabolite
chlorine chloride : A halide anion formed when chlorine picks up an electron to form an an anion.	4.05	15	0	halide anion; monoatomic chlorine	cofactor; Escherichia coli metabolite; human metabolite
hydrochloric acid Hydrochloric Acid: A strong corrosive acid that is commonly used as a laboratory reagent. It is formed by dissolving hydrogen chloride in water. GASTRIC ACID is the hydrochloric acid component of GASTRIC JUICE.. hydrogen chloride : A mononuclear parent hydride consisting of covalently bonded hydrogen and chlorine atoms.	2.89	4	0	chlorine molecular entity; gas molecular entity; hydrogen halide; mononuclear parent hydride	mouse metabolite
coumarin 2H-chromen-2-one: coumarin derivative	2.66	3	0	coumarins	fluorescent dye; human metabolite; plant metabolite
4-hydroxymandelic acid 4-hydroxymandelic acid: RN given refers to cpd without isomeric designation. 4-hydroxymandelic acid : A 2-hydroxy carboxylic acid that is mandelic acid bearing a phenolic hydroxy substituent at position 4.	1.97	1	0	2-hydroxy carboxylic acid; phenols	metabolite
salicylic acid Scalp: The outer covering of the calvaria. It is composed of several layers: SKIN; subcutaneous connective tissue; the occipitofrontal muscle which includes the tendinous galea aponeurotica; loose connective tissue; and the pericranium (the PERIOSTEUM of the SKULL).	6.32	28	0	monohydroxybenzoic acid	algal metabolite; antifungal agent; antiinfective agent; EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor; keratolytic drug; plant hormone; plant metabolite
digallic acid digallic acid: structure given in first source	3.86	11	0	benzoate ester; gallate ester
phloroglucinol Phloroglucinol: A trinitrobenzene derivative with antispasmodic properties that is used primarily as a laboratory reagent.. phloroglucinol : A benzenetriol with hydroxy groups at position 1, 3 and 5.	3.24	6	0	benzenetriol; phenolic donor	algal metabolite
octanoic acid octanoic acid: RN given refers to parent cpd; structure in Merck Index, 9th ed, #1764. octanoic acid : A straight-chain saturated fatty acid that is heptane in which one of the hydrogens of a terminal methyl group has been replaced by a carboxy group. Octanoic acid is also known as caprylic acid.	3.86	3	0	medium-chain fatty acid; straight-chain saturated fatty acid	antibacterial agent; Escherichia coli metabolite; human metabolite
hydrogen sulfide Hydrogen Sulfide: A flammable, poisonous gas with a characteristic odor of rotten eggs. It is used in the manufacture of chemicals, in metallurgy, and as an analytical reagent. (From Merck Index, 11th ed). hydrogen sulfide : A sulfur hydride consisting of a single sulfur atom bonded to two hydrogen atoms. A highly poisonous, flammable gas with a characteristic odour of rotten eggs, it is often produced by bacterial decomposition of organic matter in the absence of oxygen.. thiol : An organosulfur compound in which a thiol group, -SH, is attached to a carbon atom of any aliphatic or aromatic moiety.	2.05	1	0	gas molecular entity; hydracid; mononuclear parent hydride; sulfur hydride	Escherichia coli metabolite; genotoxin; metabolite; signalling molecule; toxin; vasodilator agent
4-aminophenol 4-aminophenol: RN given refers to parent cpd. 4-aminophenol : An amino phenol (one of the three possible isomers) which has the single amino substituent located para to the phenolic -OH group.	3.1	1	0	aminophenol	allergen; metabolite
bupropion Bupropion: A propiophenone-derived antidepressant and antismoking agent that inhibits the uptake of DOPAMINE.. bupropion : An aromatic ketone that is propiophenone carrying a tert-butylamino group at position 2 and a chloro substituent at position 3 on the phenyl ring.	2.1	1	0	aromatic ketone; monochlorobenzenes; secondary amino compound	antidepressant; environmental contaminant; xenobiotic
guaiacol Guaiacol: An agent thought to have disinfectant properties and used as an expectorant. (From Martindale, The Extra Pharmacopoeia, 30th ed, p747). methylcatechol : Any member of the class of catechols carrying one or more methyl substituents.. guaiacol : A monomethoxybenzene that consists of phenol with a methoxy substituent at the ortho position.	3.6	9	0	guaiacols	disinfectant; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; expectorant; plant metabolite
hippuric acid hippuric acid: RN given refers to parent cpd; structure in Merck Index, 9th ed, #4591. N-benzoylglycine : An N-acylglycine in which the acyl group is specified as benzoyl.	4.79	2	1	N-acylglycine	human blood serum metabolite; uremic toxin
malic acid malic acid : A 2-hydroxydicarboxylic acid that is succinic acid in which one of the hydrogens attached to a carbon is replaced by a hydroxy group.. 2-hydroxydicarboxylic acid : Any dicarboxylic acid carrying a hydroxy group on the carbon atom at position alpha to the carboxy group.	2.73	3	0	2-hydroxydicarboxylic acid; C4-dicarboxylic acid	food acidity regulator; fundamental metabolite
phosphonoacetic acid Phosphonoacetic Acid: A simple organophosphorus compound that inhibits DNA polymerase, especially in viruses and is used as an antiviral agent.. phosphonoacetic acid : A member of the class of phosphonic acids that is phosphonic acid in which the hydrogen attached to the phosphorous is replaced by a carboxymethyl group.	2	1	0	monocarboxylic acid; phosphonic acids	antiviral agent; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor
3,4-dihydroxyphenylacetic acid 3,4-Dihydroxyphenylacetic Acid: A deaminated metabolite of LEVODOPA.. (3,4-dihydroxyphenyl)acetic acid : A dihydroxyphenylacetic acid having the two hydroxy substituents located at the 3- and 4-positions. It is a metabolite of dopamine.. dihydroxyphenylacetic acid : A dihydroxy monocarboxylic acid consisting of phenylacetic acid having two phenolic hydroxy substituents.	5.71	7	1	catechols; dihydroxyphenylacetic acid	human metabolite
glucono-1,4-lactone [no description available]	1.96	1	0	gamma-lactone
lactic acid Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.	7.77	3	0	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
dimethyl sulfoxide Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.	3.27	6	0	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
formaldehyde paraform: polymerized formaldehyde; RN given refers to parent cpd; used in root canal therapy	8.39	7	0	aldehyde; one-carbon compound	allergen; carcinogenic agent; disinfectant; EC 3.5.1.4 (amidase) inhibitor; environmental contaminant; Escherichia coli metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
glycine [no description available]	4.35	6	0	alpha-amino acid; amino acid zwitterion; proteinogenic amino acid; serine family amino acid	EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor; fundamental metabolite; hepatoprotective agent; micronutrient; neurotransmitter; NMDA receptor agonist; nutraceutical
glycerol Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.	4.11	14	0	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
glycolic acid glycolic acid: RN given refers to parent cpd. glycolic acid : A 2-hydroxy monocarboxylic acid that is acetic acid where the methyl group has been hydroxylated.	2.15	1	0	2-hydroxy monocarboxylic acid; primary alcohol	keratolytic drug; metabolite
hydrogen carbonate Bicarbonates: Inorganic salts that contain the -HCO3 radical. They are an important factor in determining the pH of the blood and the concentration of bicarbonate ions is regulated by the kidney. Levels in the blood are an index of the alkali reserve or buffering capacity.. hydrogencarbonate : The carbon oxoanion resulting from the removal of a proton from carbonic acid.	2.69	3	0	carbon oxoanion	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
histamine [no description available]	3.99	14	0	aralkylamino compound; imidazoles	human metabolite; mouse metabolite; neurotransmitter
homogentisic acid Homogentisic Acid: Dihydroxyphenylacetic acid with hydroxyls at the 2 and 5 positions of the phenyl ring.. homogentisic acid : A dihydroxyphenylacetic acid having the two hydroxy substituents at the 2- and 5-positions.	2.71	3	0	dihydroxyphenylacetic acid; hydroquinones	human metabolite; plant metabolite
hydrogen Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.	3.67	9	0	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
hydroquinone [no description available]	4.91	11	0	benzenediol; hydroquinones	antioxidant; carcinogenic agent; cofactor; Escherichia coli metabolite; human xenobiotic metabolite; mouse metabolite; skin lightening agent
imidazole imidazole: RN given refers to parent cpd. 1H-imidazole : An imidazole tautomer which has the migrating hydrogen at position 1.	1.97	1	0	imidazole
indole [no description available]	2.78	3	0	indole; polycyclic heteroarene	Escherichia coli metabolite
indoleacetic acid indoleacetic acid: RN given refers to unlabeled parent cpd; structure in Merck Index, 9th ed, #4841. auxin : Any of a group of compounds, both naturally occurring and synthetic, that induce cell elongation in plant stems (from Greek alphaupsilonxialphanuomega, "to grow").. indole-3-acetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group.	2.53	2	0	indole-3-acetic acids; monocarboxylic acid	auxin; human metabolite; mouse metabolite; plant hormone; plant metabolite
iodine Iodine: A nonmetallic element of the halogen group that is represented by the atomic symbol I, atomic number 53, and atomic weight of 126.90. It is a nutritionally essential element, especially important in thyroid hormone synthesis. In solution, it has anti-infective properties and is used topically.. diiodine : Molecule comprising two covalently bonded iodine atoms with overall zero charge..	2.02	1	0	diatomic iodine	nutrient
dihydroxyphenylalanine Dihydroxyphenylalanine: A beta-hydroxylated derivative of phenylalanine. The D-form of dihydroxyphenylalanine has less physiologic activity than the L-form and is commonly used experimentally to determine whether the pharmacological effects of LEVODOPA are stereospecific.. dopa : A hydroxyphenylalanine carrying hydroxy substituents at positions 3 and 4 of the benzene ring.	2.87	4	0	hydroxyphenylalanine; non-proteinogenic alpha-amino acid; tyrosine derivative	human metabolite
pipecolic acid pipecolic acid: RN given refers to cpd without isomeric designation. pipecolic acid : A piperidinemonocarboxylic acid in which the carboxy group is located at position C-2.. pipecolate : A piperidinecarboxylate that is the conjugate base of pipecolic acid.	2.01	1	0	piperidinemonocarboxylic acid
2,3,4,5-tetrahydroxypentanal [no description available]	2.6	1	0	hydroxyaldehyde; pentose; polyol
lipoamide Lipozyme: lipase from Rhizomucor miehei immobilized on anion exchange resin	2.46	2	0	dithiolanes; monocarboxylic acid amide	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
thioctic acid Thioctic Acid: An octanoic acid bridged with two sulfurs so that it is sometimes also called a pentanoic acid in some naming schemes. It is biosynthesized by cleavage of LINOLEIC ACID and is a coenzyme of oxoglutarate dehydrogenase (KETOGLUTARATE DEHYDROGENASE COMPLEX). It is used in DIETARY SUPPLEMENTS.	2.08	1	0	dithiolanes; heterocyclic fatty acid; thia fatty acid	fundamental metabolite; geroprotector
pyruvaldehyde Pyruvaldehyde: An organic compound used often as a reagent in organic synthesis, as a flavoring agent, and in tanning. It has been demonstrated as an intermediate in the metabolism of acetone and its derivatives in isolated cell preparations, in various culture media, and in vivo in certain animals.. methylglyoxal : A 2-oxo aldehyde derived from propanal.	3.94	11	0	2-oxo aldehyde; propanals	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
methanol Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.	6.58	60	0	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
phytic acid Phytic Acid: Complexing agent for removal of traces of heavy metal ions. It acts also as a hypocalcemic agent.. myo-inositol hexakisphosphate : A myo-inositol hexakisphosphate in which each hydroxy group of myo-inositol is monophosphorylated.	2.59	2	0	inositol phosphate
inositol Inositol: An isomer of glucose that has traditionally been considered to be a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in man. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1379) Inositol phospholipids are important in signal transduction.. inositol : Any cyclohexane-1,2,3,4,5,6-hexol.. 1D-chiro-inositol : Belonging to the inositol family of compounds, D-chiro-inositol (DCI) is an isomer of glucose. It is an important secondary messenger in insulin signal transduction.. muco-inositol : An inositol that is cyclohexane-1,2,3,4,5,6-hexol having a (1R,2R,3r,4R,5S,6r)-configuration.	8.84	3	0	cyclitol; hexol
melatonin [no description available]	4.14	4	0	acetamides; tryptamines	anticonvulsant; central nervous system depressant; geroprotector; hormone; human metabolite; immunological adjuvant; mouse metabolite; radical scavenger
croton oil [no description available]	7.1	1	0	N-acyl-hexosamine
n-acetylserotonin N-acetylserotonin : An N-acylserotonin resulting from the formal condensation of the primary amino group of serotonin with the carboxy group of acetic acid.	2.17	1	0	acetamides; N-acylserotonin; phenols	antioxidant; human metabolite; mouse metabolite; tropomyosin-related kinase B receptor agonist
naringenin [no description available]	3.95	3	0	4'-hydroxyflavanones; trihydroxyflavanone
nickel Nickel: A trace element with the atomic symbol Ni, atomic number 28, and atomic weight 58.69. It is a cofactor of the enzyme UREASE.. nickel ion : A nickel atom having a net electric charge.. nickel atom : Chemical element (nickel group element atom) with atomic number 28.	3.48	8	0	metal allergen; nickel group element atom	epitope; micronutrient
niacinamide nicotinamide : A pyridinecarboxamide that is pyridine in which the hydrogen at position 3 is replaced by a carboxamide group.	9.28	4	1	pyridine alkaloid; pyridinecarboxamide; vitamin B3	anti-inflammatory agent; antioxidant; cofactor; EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; Escherichia coli metabolite; geroprotector; human urinary metabolite; metabolite; mouse metabolite; neuroprotective agent; Saccharomyces cerevisiae metabolite; Sir2 inhibitor
niacin Niacin: A water-soluble vitamin of the B complex occurring in various animal and plant tissues. It is required by the body for the formation of coenzymes NAD and NADP. It has PELLAGRA-curative, vasodilating, and antilipemic properties.. vitamin B3 : Any member of a group of vitamers that belong to the chemical structural class called pyridines that exhibit biological activity against vitamin B3 deficiency. Vitamin B3 deficiency causes a condition known as pellagra whose symptoms include depression, dermatitis and diarrhea. The vitamers include nicotinic acid and nicotinamide (and their ionized and salt forms).. nicotinic acid : A pyridinemonocarboxylic acid that is pyridine in which the hydrogen at position 3 is replaced by a carboxy group.	2.98	4	0	pyridine alkaloid; pyridinemonocarboxylic acid; vitamin B3	antidote; antilipemic drug; EC 3.5.1.19 (nicotinamidase) inhibitor; Escherichia coli metabolite; human urinary metabolite; metabolite; mouse metabolite; plant metabolite; vasodilator agent
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	3.73	10	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
nitric acid Nitric Acid: Nitric acid (HNO3). A colorless liquid that is used in the manufacture of inorganic and organic nitrates and nitro compounds for fertilizers, dye intermediates, explosives, and many different organic chemicals. Continued exposure to vapor may cause chronic bronchitis; chemical pneumonitis may occur. (From Merck Index, 11th ed). nitric acid : A nitrogen oxoacid of formula HNO3 in which the nitrogen atom is bonded to a hydroxy group and by equivalent bonds to the remaining two oxygen atoms.	1.99	1	0	nitrogen oxoacid	protic solvent; reagent
nitrites Nitrites: Salts of nitrous acid or compounds containing the group NO2-. The inorganic nitrites of the type MNO2 (where M=metal) are all insoluble, except the alkali nitrites. The organic nitrites may be isomeric, but not identical with the corresponding nitro compounds. (Grant & Hackh's Chemical Dictionary, 5th ed)	3.6	9	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species	human metabolite
nitrous oxide Nitrous Oxide: Nitrogen oxide (N2O). A colorless, odorless gas that is used as an anesthetic and analgesic. High concentrations cause a narcotic effect and may replace oxygen, causing death by asphyxia. It is also used as a food aerosol in the preparation of whipping cream.. dinitrogen oxide : A nitrogen oxide consisting of linear unsymmetrical molecules with formula N2O. While it is the most used gaseous anaesthetic in the world, its major commercial use, due to its solubility under pressure in vegetable fats combined with its non-toxicity in low concentrations, is as an aerosol spray propellant and aerating agent for canisters of 'whipped' cream.	7.57	2	0	gas molecular entity; nitrogen oxide	analgesic; bacterial metabolite; food packaging gas; food propellant; general anaesthetic; greenhouse gas; inhalation anaesthetic; NMDA receptor antagonist; raising agent; refrigerant; vasodilator agent
n,n-dimethylaniline N,N-dimethylaniline: RN given refers to parent cpd; structure. dimethylaniline : A methylaniline carrying at least two methyl groups.. N,N-dimethylaniline : A tertiary amine that is aniline in which the amino hydrogens are replaced by two methyl groups.	3.1	1	0	dimethylaniline; tertiary amine
1-octanol 1-Octanol: A colorless, slightly viscous liquid used as a defoaming or wetting agent. It is also used as a solvent for protective coatings, waxes, and oils, and as a raw material for plasticizers. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). octan-1-ol : An octanol carrying the hydroxy group at position 1.	2.75	3	0	octanol; primary alcohol	antifungal agent; bacterial metabolite; fuel additive; kairomone; plant metabolite
hydroxide ion [no description available]	2.25	1	0	oxygen hydride	mouse metabolite
oxalic acid Oxalic Acid: A strong dicarboxylic acid occurring in many plants and vegetables. It is produced in the body by metabolism of glyoxylic acid or ascorbic acid. It is not metabolized but excreted in the urine. It is used as an analytical reagent and general reducing agent.. oxalic acid : An alpha,omega-dicarboxylic acid that is ethane substituted by carboxyl groups at positions 1 and 2.	2.03	1	0	alpha,omega-dicarboxylic acid	algal metabolite; human metabolite; plant metabolite
4-aminobenzoic acid 4-Aminobenzoic Acid: An aminobenzoic acid isomer that combines with pteridine and GLUTAMIC ACID to form FOLIC ACID. The fact that 4-aminobenzoic acid absorbs light throughout the UVB range has also resulted in its use as an ingredient in SUNSCREENS.. 4-ammoniobenzoate : A zwitterion obtained by transfer of a proton from the carboxy to the amino group of 4-aminobenzoic acid.. 4-aminobenzoic acid : An aminobenzoic acid in which the amino group is para to the carboxy group.	3.28	6	0	aminobenzoic acid; aromatic amino-acid zwitterion	allergen; Escherichia coli metabolite; plant metabolite
4-nitrophenol 4-nitrophenol: RN given refers to parent cpd. mononitrophenol : A nitrophenol that is phenol carrying a single nitro substituent at unspecified position.. 4-nitrophenol : A member of the class of 4-nitrophenols that is phenol in which the hydrogen that is para to the hydroxy group has been replaced by a nitro group.	3.1	1	0	4-nitrophenols	human xenobiotic metabolite; mouse metabolite
palmitic acid Palmitic Acid: A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids.. hexadecanoic acid : A straight-chain, sixteen-carbon, saturated long-chain fatty acid.	3.69	9	0	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; EC 1.1.1.189 (prostaglandin-E2 9-reductase) inhibitor; plant metabolite
pentachlorophenol PENTA: structure given in first source	7.44	2	0	aromatic fungicide; chlorophenol; organochlorine pesticide; pentachlorobenzenes	human xenobiotic metabolite
phenanthrene phenanthrene : A polycyclic aromatic hydrocarbon composed of three fused benzene rings which takes its name from the two terms 'phenyl' and 'anthracene.'	2.31	1	0	ortho-fused polycyclic arene; ortho-fused tricyclic hydrocarbon; phenanthrenes	environmental contaminant; mouse metabolite
phenol [no description available]	6	32	0	phenols	antiseptic drug; disinfectant; human xenobiotic metabolite; mouse metabolite
phenylacetaldehyde [no description available]	7.59	2	0	alpha-CH2-containing aldehyde; phenylacetaldehydes	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
phenylacetic acid phenylacetic acid : A monocarboxylic acid that is toluene in which one of the hydrogens of the methyl group has been replaced by a carboxy group.	2.39	2	0	benzenes; monocarboxylic acid; phenylacetic acids	allergen; Aspergillus metabolite; auxin; EC 6.4.1.1 (pyruvate carboxylase) inhibitor; Escherichia coli metabolite; human metabolite; plant growth retardant; plant metabolite; Saccharomyces cerevisiae metabolite; toxin
phenethylamine phenethylamine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7016. 2-phenylethylamine : A phenylethylamine having the phenyl substituent at the 2-position.	2.17	1	0	alkaloid; aralkylamine; phenylethylamine	Escherichia coli metabolite; human metabolite; mouse metabolite
phosphoenolpyruvate Phosphoenolpyruvate: A monocarboxylic acid anion derived from selective deprotonation of the carboxy group of phosphoenolpyruvic acid. It is a metabolic intermediate in GLYCOLYSIS; GLUCONEOGENESIS; and other pathways.. phosphoenolpyruvate : A monocarboxylic acid anion resuting from selective deprotonation of the carboxy group of phosphoenolpyruvic acid.. phosphoenolpyruvic acid : A monocarboxylic acid that is acrylic acid substituted by a phosphonooxy group at position 2. It is a metabolic intermediate in pathways like glycolysis and gluconeogenesis.	2	1	0	carboxyalkyl phosphate; monocarboxylic acid	fundamental metabolite
phosphorylcholine Phosphorylcholine: Calcium and magnesium salts used therapeutically in hepatobiliary dysfunction.. phosphocholine : The phosphate of choline; and the parent compound of the phosphocholine family.	1.99	1	0	phosphocholines	allergen; epitope; hapten; human metabolite; mouse metabolite
phthalic acid phthalic acid: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7178. phthalic acid : A benzenedicarboxylic acid cosisting of two carboxy groups at ortho positions.	2.37	2	0	benzenedicarboxylic acid	human xenobiotic metabolite
picolinic acid picolinic acid: iron-chelating agent that inhibits DNA synthesis; may interfere with iron-dependent production of stable free organic radical which is essential for ribonucleotide reductase formation of deoxyribonucleotides; RN given refers to parent cpd; structure in Merck Index, 9th ed, #7206. picolinic acid : A pyridinemonocarboxylic acid in which the carboxy group is located at position 2. It is an intermediate in the metabolism of tryptophan.	2.1	1	0	pyridinemonocarboxylic acid	human metabolite; MALDI matrix material
propylene glycol Propylene Glycol: A clear, colorless, viscous organic solvent and diluent used in pharmaceutical preparations.. propane-1,2-diol : The simplest member of the class of propane-1,2-diols, consisting of propane in which a hydrogen at position 1 and a hydrogen at position 2 are substituted by hydroxy groups. A colourless, viscous, hygroscopic, low-melting (-59degreeC) and high-boiling (188degreeC) liquid with low toxicity, it is used as a solvent, emulsifying agent, and antifreeze.	2.48	2	0	glycol; propane-1,2-diols	allergen; human xenobiotic metabolite; mouse metabolite; protic solvent
1-propanol 1-Propanol: A colorless liquid made by oxidation of aliphatic hydrocarbons that is used as a solvent and chemical intermediate.. propan-1-ol : The parent member of the class of propan-1-ols that is propane in which a hydrogen of one of the methyl groups is replaced by a hydroxy group.	2.87	4	0	propan-1-ols; short-chain primary fatty alcohol	metabolite; protic solvent
propionic acid propionic acid : A short-chain saturated fatty acid comprising ethane attached to the carbon of a carboxy group.	2.1	1	0	saturated fatty acid; short-chain fatty acid	antifungal drug
pteridines [no description available]	2.17	1	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; pteridines
putrescine [no description available]	2.17	1	0	alkane-alpha,omega-diamine	antioxidant; fundamental metabolite
pyridine azine : An organonitrogen compound of general structure RCH=N-N=CHR or RR'C=N-N=CRR'.	1.98	1	0	azaarene; mancude organic heteromonocyclic parent; monocyclic heteroarene; pyridines	environmental contaminant; NMR chemical shift reference compound
pyridoxal phosphate Pyridoxal Phosphate: This is the active form of VITAMIN B 6 serving as a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into pyridoxamine phosphate (PYRIDOXAMINE).. pyridoxal 5'-phosphate : The monophosphate ester obtained by condensation of phosphoric acid with the primary hydroxy group of pyridoxal.	2.02	1	0	methylpyridines; monohydroxypyridine; pyridinecarbaldehyde; vitamin B6 phosphate	coenzyme; cofactor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
pyridoxamine [no description available]	2.1	1	0	aminoalkylpyridine; hydroxymethylpyridine; monohydroxypyridine; vitamin B6	Escherichia coli metabolite; human metabolite; iron chelator; mouse metabolite; nephroprotective agent; plant metabolite; Saccharomyces cerevisiae metabolite
pyridoxine 4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol: structure in first source. vitamin B6 : Any member of the group of pyridines that exhibit biological activity against vitamin B6 deficiency. Vitamin B6 deficiency is associated with microcytic anemia, electroencephalographic abnormalities, dermatitis with cheilosis (scaling on the lips and cracks at the corners of the mouth) and glossitis (swollen tongue), depression and confusion, and weakened immune function. Vitamin B6 consists of the vitamers pyridoxine, pyridoxal, and pyridoxamine and their respective 5'-phosphate esters (and includes their corresponding ionized and salt forms).	2.39	2	0	hydroxymethylpyridine; methylpyridines; monohydroxypyridine; vitamin B6	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
pyrogallol benzenetriol : A triol in which three hydroxy groups are substituted onto a benzene ring.	8.56	70	1	benzenetriol; phenolic donor	plant metabolite
pyruvic acid Pyruvic Acid: An intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed). pyruvic acid : A 2-oxo monocarboxylic acid that is the 2-keto derivative of propionic acid. It is a metabolite obtained during glycolysis.	2.8	3	0	2-oxo monocarboxylic acid	cofactor; fundamental metabolite
quinolinic acid Quinolinic Acid: A metabolite of tryptophan with a possible role in neurodegenerative disorders. Elevated CSF levels of quinolinic acid are correlated with the severity of neuropsychological deficits in patients who have AIDS.. pyridinedicarboxylic acid : Any member of the class of pyridines carrying two carboxy groups.. quinolinic acid : A pyridinedicarboxylic acid that is pyridine substituted by carboxy groups at positions 2 and 3. It is a metabolite of tryptophan.	7.49	2	0	pyridinedicarboxylic acid	Escherichia coli metabolite; human metabolite; mouse metabolite; NMDA receptor agonist
dimethyl sulfide dimethyl sulfide: structure. dimethyl sulfide : A methyl sulfide in which the sulfur atom is substituted by two methyl groups. It is produced naturally by some marine algae.. methyl sulfide : Any aliphatic sulfide in which at least one of the organyl groups attached to the sulfur is a methyl group.	2.17	1	0	aliphatic sulfide	algal metabolite; bacterial xenobiotic metabolite; EC 3.5.1.4 (amidase) inhibitor; Escherichia coli metabolite; marine metabolite
sulfites Sulfites: Inorganic salts of sulfurous acid.. sulfites : Any sulfurous acid derivative that is a salt or an ester of sulfurous acid.. organosulfonate oxoanion : An organic anion obtained by deprotonation of the sufonate group(s) of any organosulfonic acid.. sulfite : A sulfur oxoanion that is the conjugate base of hydrogen sulfite (H2SO3).	2.68	3	0	divalent inorganic anion; sulfur oxide; sulfur oxoanion
spermine [no description available]	2.01	1	0	polyazaalkane; tetramine	antioxidant; fundamental metabolite; immunosuppressive agent
succinic acid Succinic Acid: A water-soluble, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. (Hawley's Condensed Chemical Dictionary, 12th ed, p1099; McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed, p1851). succinic acid : An alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle.	4.18	5	0	alpha,omega-dicarboxylic acid; C4-dicarboxylic acid	anti-ulcer drug; fundamental metabolite; micronutrient; nutraceutical; radiation protective agent
sulfuric acid sulfuric acid : A sulfur oxoacid that consists of two oxo and two hydroxy groups joined covalently to a central sulfur atom.	2.47	2	0	sulfur oxoacid	catalyst
taurine [no description available]	3.78	3	0	amino sulfonic acid; zwitterion	antioxidant; Escherichia coli metabolite; glycine receptor agonist; human metabolite; mouse metabolite; nutrient; radical scavenger; Saccharomyces cerevisiae metabolite
thiamine thiamine(1+) : A primary alcohol that is 1,3-thiazol-3-ium substituted by (4-amino-2-methylpyrimidin-5-yl)methyl, methyl and 2-hydroxyethyl groups at positions 3, 4 and 5, respectively.	2.35	2	0	primary alcohol; vitamin B1	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
toluene methylbenzene : Any alkylbenzene that is benzene substituted with one or more methyl groups.	2.66	3	0	methylbenzene; toluenes; volatile organic compound	cholinergic antagonist; fuel additive; neurotoxin; non-polar solvent
trimethylamine [no description available]	2.57	2	0	methylamines; tertiary amine	Escherichia coli metabolite; human xenobiotic metabolite
tryptophan [no description available]	3.54	2	0	alpha-amino acid; amino acid zwitterion; aminoalkylindole; aromatic amino acid; polar amino acid	Daphnia magna metabolite
tryptamine [no description available]	7.52	2	0	aminoalkylindole; aralkylamino compound; indole alkaloid; tryptamines	human metabolite; mouse metabolite; plant metabolite
uric acid Uric Acid: An oxidation product, via XANTHINE OXIDASE, of oxypurines such as XANTHINE and HYPOXANTHINE. It is the final oxidation product of purine catabolism in humans and primates, whereas in most other mammals URATE OXIDASE further oxidizes it to ALLANTOIN.. uric acid : An oxopurine that is the final oxidation product of purine metabolism.. 6-hydroxy-1H-purine-2,8(7H,9H)-dione : A tautomer of uric acid having oxo groups at C-2 and C-8 and a hydroxy group at C-6.. 7,9-dihydro-1H-purine-2,6,8(3H)-trione : An oxopurine in which the purine ring is substituted by oxo groups at positions 2, 6, and 8.	7.32	17	2	uric acid	Escherichia coli metabolite; human metabolite; mouse metabolite
urea pseudourea: clinical use; structure. isourea : A carboximidic acid that is the imidic acid tautomer of urea, H2NC(=NH)OH, and its hydrocarbyl derivatives.	8.14	5	0	isourea; monocarboxylic acid amide; one-carbon compound	Daphnia magna metabolite; Escherichia coli metabolite; fertilizer; flour treatment agent; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
vanillin Vanilla: A plant genus of the family ORCHIDACEAE that is the source of the familiar flavoring used in foods and medicines (FLAVORING AGENTS).	5.23	15	0	benzaldehydes; monomethoxybenzene; phenols	anti-inflammatory agent; anticonvulsant; antioxidant; flavouring agent; plant metabolite
catechin [no description available]	4.39	6	0	hydroxyflavan
2-amino-5-phosphonovalerate 2-Amino-5-phosphonovalerate: The D-enantiomer is a potent and specific antagonist of NMDA glutamate receptors (RECEPTORS, N-METHYL-D-ASPARTATE). The L form is inactive at NMDA receptors but may affect the AP4 (2-amino-4-phosphonobutyrate; APB) excitatory amino acid receptors.	2.69	3	0	non-proteinogenic alpha-amino acid	NMDA receptor antagonist
alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid: An IBOTENIC ACID homolog and glutamate agonist. The compound is the defining agonist for the AMPA subtype of glutamate receptors (RECEPTORS, AMPA). It has been used as a radionuclide imaging agent but is more commonly used as an experimental tool in cell biological studies.	2.73	3	0	non-proteinogenic alpha-amino acid
ibotenic acid Ibotenic Acid: A neurotoxic isoxazole (similar to KAINIC ACID and MUSCIMOL) found in AMANITA mushrooms. It causes motor depression, ataxia, and changes in mood, perceptions and feelings, and is a potent excitatory amino acid agonist.	2	1	0	non-proteinogenic alpha-amino acid	neurotoxin
gallopamil Gallopamil: Coronary vasodilator that is an analog of iproveratril (VERAPAMIL) with one more methoxy group on the benzene ring.	3.67	10	0	benzenes; organic amino compound
vanilmandelic acid Vanilmandelic Acid: A 3-O-methyl ether of 3,4-dihydroxymandelic acid. It is an end-stage metabolite of CATECHOLAMINES; EPINEPHRINE; and NOREPINEPHRINE.. vanillylmandelic acid : An aromatic ether that is the 3-O-methyl ether of 3,4-dihydroxymandelic acid.	1.97	1	0	2-hydroxy monocarboxylic acid; aromatic ether; phenols	human metabolite
menthol Menthol: A monoterpene cyclohexanol produced from mint oils.	3.8	3	0	p-menthane monoterpenoid; secondary alcohol	volatile oil component
5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl 3,4,5-trihydroxybenzoate [no description available]	2.17	1	0	catechin
mandelic acid SAMMA: mandelic acid condensation polymer	1.96	1	0	2-hydroxy monocarboxylic acid; benzenes	antibacterial agent; human xenobiotic metabolite
1,10-phenanthroline 1,10-phenanthroline: RN given refers to parent cpd; inhibits Zn-dependent metalloproteinases	7.06	1	0	phenanthroline	EC 2.7.1.1 (hexokinase) inhibitor; EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor
1,2-dimethylhydrazine 1,2-Dimethylhydrazine: A DNA alkylating agent that has been shown to be a potent carcinogen and is widely used to induce colon tumors in experimental animals.. 1,2-dimethylhydrazine : A member of the class of hydrazines that is hydrazine in which one of the hydrogens attached to each nitrogen is replaced by a methyl group. A powerful DNA alkylating agent and carcinogen, it is used to induce colon cancer in laboratory rats and mice.	3.04	4	0	hydrazines	alkylating agent; carcinogenic agent
1,2-dioctanoylglycerol 1,2-dioctanoylglycerol: functions as bioregulator of protein kinase C in human platelets	2.38	2	0
1,3-dipropyl-8-cyclopentylxanthine DPCPX : An oxopurine that is 7H-xanthine substituted at positions 1 and 3 by propyl groups and at position 8 by a cyclohexyl group.	2	1	0	oxopurine	adenosine A1 receptor antagonist; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor
1-anilino-8-naphthalenesulfonate 1-anilino-8-naphthalenesulfonate: RN given refers to parent cpd. 8-anilinonaphthalene-1-sulfonic acid : A naphthalenesulfonic acid that is naphthalene-1-sulfonic acid substituted by a phenylamino group at position 8.	3.68	9	0	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
edelfosine edelfosine: RN given refers to parent cpd. edelfosine : A racemate comprising equimolar amounts of (R)- and (S)-edelfosine.. 1-octadecyl-2-methylglycero-3-phosphocholine : A glycerophosphocholine that is glycero-3-phosphocholine substituted at positions 1 and 2 by octadecyl and methyl groups respectively.	1.99	1	0	glycerophosphocholine
n-(3-(aminomethyl)benzyl)acetamidine N-(3-(aminomethyl)benzyl)acetamidine: structure in first source. N-[3-(aminomethyl)benzyl]acetamidine : An aralkylamine that is Nbenzylacetamidine substituted at position 3 on the benzene ring by an aminomethyl group. An inhibitor of nitric oxide synthase.	2.07	1	0	aralkylamine; carboxamidine; primary amino compound	angiogenesis inhibitor; EC 1.14.13.39 (nitric oxide synthase) inhibitor; geroprotector
1h-(1,2,4)oxadiazolo(4,3-a)quinoxalin-1-one 1H-(1,2,4)oxadiazolo(4,3-a)quinoxalin-1-one: structure given in first source; inhibits guanylyl cyclase. 1H-[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one : A member of the class of oxadiazoloquinoxalines that is 1H-[1,2,4]oxadiazolo[4,3-a]quinoxaline substituted at position 1 by an oxo group.	2.01	1	0	oxadiazoloquinoxaline	EC 4.6.1.2 (guanylate cyclase) inhibitor
2,4-dichlorophenoxyacetic acid 2,4-Dichlorophenoxyacetic Acid: An herbicide with irritant effects on the eye and the gastrointestinal system.. 2,4-D : A chlorophenoxyacetic acid that is phenoxyacetic acid in which the ring hydrogens at postions 2 and 4 are substituted by chlorines.	2.77	3	0	chlorophenoxyacetic acid; dichlorobenzene	agrochemical; defoliant; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; environmental contaminant; phenoxy herbicide; synthetic auxin
beta-resorcylic acid beta-resorcylic acid: RN given refers to parent cpd; structure	2.93	4	0
2,4-dinitrophenol 2,4-Dinitrophenol: A toxic dye, chemically related to trinitrophenol (picric acid), used in biochemical studies of oxidative processes where it uncouples oxidative phosphorylation. It is also used as a metabolic stimulant. (Stedman, 26th ed). dinitrophenol : Members of the class of nitrophenol carrying two nitro substituents.. 2,4-dinitrophenol : A dinitrophenol having the nitro groups at the 2- and 4-positions.	2.02	1	0	dinitrophenol	allergen; antiseptic drug; bacterial xenobiotic metabolite; geroprotector; oxidative phosphorylation inhibitor
2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine: mutagen from fried ground beef; structure given in first source. PhIP : An imidazopyridine that is 1H--imidazo[4,5-b]pyridine which is substituted at positions 1, 2, and 6 by methyl, amino, and phenyl groups, respectively. It is the most abundant of the mutagenic heterocyclic amines found in cooked meat and fish.	2.39	2	0	imidazopyridine; primary amino compound	carcinogenic agent; mutagen
2-aminofluorene [no description available]	3.1	1	0
mercaptoethanol Mercaptoethanol: A water-soluble thiol derived from hydrogen sulfide and ethanol. It is used as a reducing agent for disulfide bonds and to protect sulfhydryl groups from oxidation.	2.65	3	0	alkanethiol; primary alcohol	geroprotector
2-aminoethoxydiphenyl borate 2-aminoethoxydiphenyl borate: is a novel membrane-penetrable modulator and transient receptor potential channel blocker; structure in first source; do not confuse with 2-APB cpd. 2-aminoethoxydiphenylborane : An organoboron compound that is diphenylborane in which the borane hydrogen is replaced by a 2-aminoethoxy group.	3.13	5	0	organoboron compound; primary amino compound	calcium channel blocker; IP3 receptor antagonist; potassium channel opener
amitrole Amitrole: A non-selective post-emergence, translocated herbicide. According to the Seventh Annual Report on Carcinogens (PB95-109781, 1994) this substance may reasonably be anticipated to be a carcinogen. (From Merck Index, 12th ed) It is an irreversible inhibitor of CATALASE, and thus impairs activity of peroxisomes.. amitrole : A member of the class of triazoles that is 1H-1,2,4-triazole substituted by an amino group at position 3. Used to control annual grasses and aquatic weeds (but not on food crops because it causes cancer in laboratory animals). Its use within the EU was banned from September 2017 on the grounds of potential groundwater contamination and risks to aquatic life; there have also been concerns about its endocrine-disrupting properties.	2	1	0	aromatic amine; triazoles	carotenoid biosynthesis inhibitor; EC 1.11.1.6 (catalase) inhibitor; herbicide
aminopropionitrile Aminopropionitrile: Reagent used as an intermediate in the manufacture of beta-alanine and pantothenic acid.	2	1	0	aminopropionitrile	antineoplastic agent; antirheumatic drug; collagen cross-linking inhibitor; plant metabolite
3-methylcholanthrene Methylcholanthrene: A carcinogen that is often used in experimental cancer studies.. 3-methylcholanthrene : A pentacyclic ortho- and peri-fused polycyclic arene consisting of a dihydrocyclopenta[ij]tetraphene ring system with a methyl substituent at the 3-position.	1.95	1	0	ortho- and peri-fused polycyclic arene	aryl hydrocarbon receptor agonist; carcinogenic agent
3-nitropropionic acid 3-nitropropionic acid: succinate dehydrogenase inactivator; biosynthesized by FABACEAE plants from ASPARAGINE. 3-nitropropanoic acid : A C-nitro compound that is propanoic acid in which one of the methyl hydrogens has been replaced by a nitro group.	2.45	2	0	C-nitro compound	antimycobacterial drug; EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor; mycotoxin; neurotoxin
4-aminopyridine [no description available]	3.08	5	0	aminopyridine; aromatic amine	avicide; orphan drug; potassium channel blocker
4-diphenylacetoxy-1,1-dimethylpiperidinium 4-diphenylacetoxy-1,1-dimethylpiperidinium: muscarinic receptor antagonist; RN given refers to parent cpd; do not confuse abbreviation 4-DAMP with a similar cpd which does not contain dimethyl groups. 4-DAMP(1+) : A quaternary ammonium salt obtained by formal methylation of the tertiary amino function of 4-diphenylacetoxy-N-methylpiperidine.	1.99	1	0	quaternary ammonium ion	cholinergic antagonist; muscarinic antagonist
homovanillic acid Homovanillic Acid: A 3-O-methyl ETHER of (3,4-dihydroxyphenyl)acetic acid.. homovanillate : A hydroxy monocarboxylic acid anion which is obtained by deprotonation of the carboxy group of homovanillic acid.. homovanillic acid : A monocarboxylic acid that is the 3-O-methyl ether of (3,4-dihydroxyphenyl)acetic acid. It is a catecholamine metabolite.	3.54	2	0	guaiacols; monocarboxylic acid	human metabolite; mouse metabolite
5,5-dimethyl-1-pyrroline-1-oxide 5,5-dimethyl-1-pyrroline-1-oxide: do not confuse with DMPO (4',5'-dihydroxy-7-methoxy-4-phenyl-5,2'-oxidocoumarin). 5,5-dimethyl-1-pyrroline N-oxide : A member of the class of 1-pyrroline nitrones (1-pyrroline N-oxides) resulting from the formal N-oxidation of 5,5-dimethyl-1-pyrroline. Used as a spin trap for the study of radicals formed by enzymatic acetaldehyde oxidation.	1.99	1	0	1-pyrroline nitrones	neuroprotective agent; spin trapping reagent
phenytoin [no description available]	3.25	1	0	imidazolidine-2,4-dione	anticonvulsant; drug allergen; sodium channel blocker; teratogenic agent
5,8,11,14-eicosatetraynoic acid 5,8,11,14-Eicosatetraynoic Acid: A 20-carbon unsaturated fatty acid containing 4 alkyne bonds. It inhibits the enzymatic conversion of arachidonic acid to prostaglandins E(2) and F(2a).	1.97	1	0	long-chain fatty acid
5-(n,n-hexamethylene)amiloride 5-(N,N-hexamethylene)amiloride: inhibitor of Na+-H+ exchange; has anti-HIV-1 activity. 5-(N,N-hexamethylene)amiloride : A member of the class of pyrazines that is amiloride in which the two amino hydrogens at position N-5 are replaced by a hexamethylene moiety, resulting in the formation of an azepane ring.	1.98	1	0	aromatic amine; azepanes; guanidines; monocarboxylic acid amide; organochlorine compound; pyrazines	antineoplastic agent; apoptosis inducer; odorant receptor antagonist; sodium channel blocker
ethylisopropylamiloride ethylisopropylamiloride: structure in first source. ethylisopropylamiloride : A member of the class of pyrazines that is amiloride in which the amino substitutent of the pyrazine ring that is adjacent to the chloro substituent has been substituted by an ethyl group and by an isopropyl group.	1.97	1	0	aromatic amine; guanidines; monocarboxylic acid amide; organochlorine compound; pyrazines; tertiary amino compound	anti-arrhythmia drug; neuroprotective agent; sodium channel blocker
hydroxyindoleacetic acid (5-hydroxyindol-3-yl)acetic acid : A member of the class of indole-3-acetic acids that is indole-3-acetic acid substituted by a hydroxy group at C-5.	2.17	1	0	indole-3-acetic acids	drug metabolite; human metabolite; mouse metabolite
5-methoxytryptamine 5-Methoxytryptamine: Serotonin derivative proposed as potentiator for hypnotics and sedatives.. 5-methoxytryptamine : A member of the class of tryptamines that is the methyl ether derivative of serotonin.	2.17	1	0	aromatic ether; primary amino compound; tryptamines	5-hydroxytryptamine 2A receptor agonist; 5-hydroxytryptamine 2B receptor agonist; 5-hydroxytryptamine 2C receptor agonist; antioxidant; cardioprotective agent; human metabolite; mouse metabolite; neuroprotective agent; radiation protective agent; serotonergic agonist
6-hydroxymelatonin 6-hydroxymelatonin : A member of the class of tryptamines that is melatonin with a hydroxy group substituent at position 6.	3.1	1	0	acetamides; tryptamines	metabolite; mouse metabolite
7,8-dihydroxyflavone 7,8-dihydroxyflavone : A dihydroxyflavone that is flavone substituted by hydroxy groups at positions 7 and 8. A dihydroxyflavone that is flavone substituted by hydroxy groups at positions 7 and 8. A naturally occurring flavonoid produced by several plants, including the weed Tridax procumbens (coalbuttons or tridax daisy) and the tree Godmania aesculifolia, In animal models, it has shown efficacy against several diseases of the nervous system, including Alzheimer's, Parkinson's, and Huntington's.	2.17	1	0	dihydroxyflavone	antidepressant; antineoplastic agent; antioxidant; plant metabolite; tropomyosin-related kinase B receptor agonist
7-chlorokynurenic acid 7-chlorokynurenic acid: selective antagonist at the glycine modulatory site of the N-methyl-D-aspartate receptor complex; structure given in first source. 7-chlorokynurenic acid : A quinolinemonocarboxylic acid that is quinaldic acid which is substituted by a hydroxy group at position 4 and by a chlorine at position 7. It is a potent NMDA glutamate receptor antagonist which antagonizes the strychnine-insensitive glycine site of the NMDA receptor. It also prevents neurodegeneration produced by quinolinic acid.	2.01	1	0	organochlorine compound; quinolinemonocarboxylic acid	neuroprotective agent; NMDA receptor antagonist
4',7-dihydroxyflavanone [no description available]	2.17	1	0	4'-hydroxyflavanones; dihydroxyflavanone; polyphenol	Brassica napus metabolite; fungal xenobiotic metabolite
7-nitroindazole 7-nitroindazole: an inhibitor of nitric oxide synthase; exhibits anti-nociceptive activity without increasing blood pressure	2.01	1	0
oxyquinoline Oxyquinoline: An antiseptic with mild fungistatic, bacteriostatic, anthelmintic, and amebicidal action. It is also used as a reagent and metal chelator, as a carrier for radio-indium for diagnostic purposes, and its halogenated derivatives are used in addition as topical anti-infective agents and oral antiamebics.. quinolin-8-ol : A monohydroxyquinoline that is quinoline substituted by a hydroxy group at position 8. Its fungicidal properties are used for the control of grey mould on vines and tomatoes.	3.1	1	0	monohydroxyquinoline	antibacterial agent; antifungal agrochemical; antiseptic drug; iron chelator
tacrine Tacrine: A cholinesterase inhibitor that crosses the blood-brain barrier. Tacrine has been used to counter the effects of muscle relaxants, as a respiratory stimulant, and in the treatment of Alzheimer's disease and other central nervous system disorders.. tacrine : A member of the class of acridines that is 1,2,3,4-tetrahydroacridine substituted by an amino group at position 9. It is used in the treatment of Alzheimer's disease.	2.74	3	0	acridines; aromatic amine	EC 3.1.1.7 (acetylcholinesterase) inhibitor
2,2'-azobis(2-amidinopropane) 2,2'-azobis(2-amidinopropane): water-soluble free-radical initiator	8.58	8	0	monoazo compound
acebutolol Acebutolol: A cardioselective beta-1 adrenergic antagonist with little effect on the bronchial receptors. The drug has stabilizing and quinidine-like effects on cardiac rhythm, as well as weak inherent sympathomimetic action.. acebutolol : An ether that is the 2-acetyl-4-(butanoylamino)phenyl ether of the primary hydroxy group of 3-(propan-2-ylamino)propane-1,2-diol.	2.1	1	0	aromatic amide; ethanolamines; ether; monocarboxylic acid amide; propanolamine; secondary amino compound	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; sympathomimetic agent
acetaminophen Acetaminophen: Analgesic antipyretic derivative of acetanilide. It has weak anti-inflammatory properties and is used as a common analgesic, but may cause liver, blood cell, and kidney damage.. paracetamol : A member of the class of phenols that is 4-aminophenol in which one of the hydrogens attached to the amino group has been replaced by an acetyl group.	4.36	6	0	acetamides; phenols	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; cyclooxygenase 3 inhibitor; environmental contaminant; ferroptosis inducer; geroprotector; hepatotoxic agent; human blood serum metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
acetazolamide Acetazolamide: One of the CARBONIC ANHYDRASE INHIBITORS that is sometimes effective against absence seizures. It is sometimes useful also as an adjunct in the treatment of tonic-clonic, myoclonic, and atonic seizures, particularly in women whose seizures occur or are exacerbated at specific times in the menstrual cycle. However, its usefulness is transient often because of rapid development of tolerance. Its antiepileptic effect may be due to its inhibitory effect on brain carbonic anhydrase, which leads to an increased transneuronal chloride gradient, increased chloride current, and increased inhibition. (From Smith and Reynard, Textbook of Pharmacology, 1991, p337)	2.75	3	0	monocarboxylic acid amide; sulfonamide; thiadiazoles	anticonvulsant; diuretic; EC 4.2.1.1 (carbonic anhydrase) inhibitor
beta-aminoethyl isothiourea beta-Aminoethyl Isothiourea: A radiation-protective agent that can inhibit DNA damage by binding to the DNA. It also increases the susceptibility of blood cells to complement-mediated lysis.	2.64	3	0
tyrphostin a23 tyrphostin A23: inhibits EGF-stimulated thymidine incorporation as well as EGF-stimulated receptor autophosphorylation & tyrosine phosphorylation & cell proliferation; structure given in first source	2.41	2	0	catechols
tyrphostin 25 [no description available]	2.04	1	0	benzenetriol
albuterol Albuterol: A short-acting beta-2 adrenergic agonist that is primarily used as a bronchodilator agent to treat ASTHMA. Albuterol is prepared as a racemic mixture of R(-) and S(+) stereoisomers. The stereospecific preparation of R(-) isomer of albuterol is referred to as levalbuterol.. albuterol : A member of the class of phenylethanolamines that is 4-(2-amino-1-hydroxyethyl)-2-(hydroxymethyl)phenol having a tert-butyl group attached to the nirogen atom. It acts as a beta-adrenergic agonist used in the treatment of asthma and chronic obstructive pulmonary disease (COPD).	1.96	1	0	phenols; phenylethanolamines; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; environmental contaminant; xenobiotic
tocopheroxy radical tocopheroxy radical: RN given refers to radical ion (1+), (2R-(2R(4R,8R*)))-isomer; RN for cpd without isomeric designation not available 12/90	2	1	0	tocopherol
alprenolol Alprenolol: One of the ADRENERGIC BETA-ANTAGONISTS used as an antihypertensive, anti-anginal, and anti-arrhythmic agent.. alprenolol : A secondary alcohol that is propan-2-ol substituted by a 2-allylphenoxy group at position 1 and an isopropylamino group at position 3. It is a beta-adrenergic antagonist used as a antihypertensive, anti-arrhythmia and a sympatholytic agent.	2.1	1	0	secondary alcohol; secondary amino compound	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; sympatholytic agent
amantadine amant: an antiviral compound consisting of an adamantane derivative chemically linked to a water-solube polyanioic matrix; structure in first source	2.1	1	0	adamantanes; primary aliphatic amine	analgesic; antiparkinson drug; antiviral drug; dopaminergic agent; NMDA receptor antagonist; non-narcotic analgesic
pimagedine pimagedine: diamine oxidase & nitric oxide synthase inhibitor; an advanced glycosylation end product inhibitor; used in the treatment of diabetic complications; structure. aminoguanidine : A one-carbon compound whose unique structure renders it capable of acting as a derivative of hydrazine, guanidine or formamide.	2.46	2	0	guanidines; one-carbon compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor; EC 1.4.3.4 (monoamine oxidase) inhibitor
p-aminohippuric acid p-Aminohippuric Acid: The glycine amide of 4-aminobenzoic acid. Its sodium salt is used as a diagnostic aid to measure effective renal plasma flow (ERPF) and excretory capacity.. p-aminohippurate : A hippurate that is the conjugate base of p-aminohippuric acid, arising from deprotonation of the carboxy group.. p-aminohippuric acid : An N-acylglycine that is the 4-amino derivative of hippuric acid; used as a diagnostic agent in the measurement of renal plasma flow.	1.99	1	0	N-acylglycine	Daphnia magna metabolite
theophylline [no description available]	3.69	10	0	dimethylxanthine	adenosine receptor antagonist; anti-asthmatic drug; anti-inflammatory agent; bronchodilator agent; drug metabolite; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; fungal metabolite; human blood serum metabolite; immunomodulator; muscle relaxant; vasodilator agent
amiodarone Amiodarone: An antianginal and class III antiarrhythmic drug. It increases the duration of ventricular and atrial muscle action by inhibiting POTASSIUM CHANNELS and VOLTAGE-GATED SODIUM CHANNELS. There is a resulting decrease in heart rate and in vascular resistance.. amiodarone : A member of the class of 1-benzofurans that is 1-benzofuran substituted by a butyl group at position 2 and a 4-[2-(diethylamino)ethoxy]-3,5-diiodobenzoyl group at position 3. It is a cardiovascular drug used for the treatment of cardiac dysrhythmias.	2.1	1	0	1-benzofurans; aromatic ketone; organoiodine compound; tertiary amino compound	cardiovascular drug
dan 2163 [no description available]	2.1	1	0	aromatic amide; aromatic amine; benzamides; pyrrolidines; sulfone	environmental contaminant; second generation antipsychotic; xenobiotic
amitriptyline Amitriptyline: Tricyclic antidepressant with anticholinergic and sedative properties. It appears to prevent the re-uptake of norepinephrine and serotonin at nerve terminals, thus potentiating the action of these neurotransmitters. Amitriptyline also appears to antagonize cholinergic and alpha-1 adrenergic responses to bioactive amines.. amitriptyline : An organic tricyclic compound that is 10,11-dihydro-5H-dibenzo[a,d][7]annulene substituted by a 3-(dimethylamino)propylidene group at position 5.	3.54	2	0	carbotricyclic compound; tertiary amine	adrenergic uptake inhibitor; antidepressant; environmental contaminant; tropomyosin-related kinase B receptor agonist; xenobiotic
amlodipine Amlodipine: A long-acting dihydropyridine calcium channel blocker. It is effective in the treatment of ANGINA PECTORIS and HYPERTENSION.. amlodipine : A fully substituted dialkyl 1,4-dihydropyridine-3,5-dicarboxylate derivative, which is used for the treatment of hypertension, chronic stable angina and confirmed or suspected vasospastic angina.	2.1	1	0	dihydropyridine; ethyl ester; methyl ester; monochlorobenzenes; primary amino compound	antihypertensive agent; calcium channel blocker; vasodilator agent
amodiaquine Amodiaquine: A 4-aminoquinoline compound with anti-inflammatory properties.. amodiaquine : A quinoline having a chloro group at the 7-position and an aryl amino group at the 4-position.	2.1	1	0	aminoquinoline; organochlorine compound; phenols; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; drug allergen; EC 2.1.1.8 (histamine N-methyltransferase) inhibitor; non-steroidal anti-inflammatory drug; prodrug
amoxapine Amoxapine: The N-demethylated derivative of the antipsychotic agent LOXAPINE that works by blocking the reuptake of norepinephrine, serotonin, or both; it also blocks dopamine receptors. Amoxapine is used for the treatment of depression.. amoxapine : A dibenzooxazepine compound having a chloro substituent at the 2-position and a piperazin-1-yl group at the 11-position.	2.1	1	0	dibenzooxazepine	adrenergic uptake inhibitor; antidepressant; dopaminergic antagonist; geroprotector; serotonin uptake inhibitor
anthralin Anthralin: An anthracene derivative that disrupts MITOCHONDRIA function and structure and is used for the treatment of DERMATOSES, especially PSORIASIS. It may cause FOLLICULITIS.. anthralin : An anthracene compound derived by the substitution of -OH groups for hydrogen at C-1 and C-8, and with an oxo group at C-9.	2.17	1	0	anthracenes	antipsoriatic
antipyrine Antipyrine: An analgesic and antipyretic that has been given by mouth and as ear drops. Antipyrine is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver. (From Martindale, The Extra Pharmacopoeia, 30th ed, p29). antipyrine : A pyrazolone derivative that is 1,2-dihydropyrazol-3-one substituted with methyl groups at N-1 and C-5 and with a phenyl group at N-2.	2.35	2	0	pyrazolone	antipyretic; cyclooxygenase 3 inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
acetovanillone apocynin : An aromatic ketone that is 1-phenylethanone substituted by a hydroxy group at position 4 and a methoxy group at position 3.	2.15	1	0	acetophenones; aromatic ketone; methyl ketone	antirheumatic drug; EC 1.6.3.1. [NAD(P)H oxidase (H2O2-forming)] inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; peripheral nervous system drug; plant metabolite
arecoline Arecoline: An alkaloid obtained from the betel nut (Areca catechu), fruit of a palm tree. It is an agonist at both muscarinic and nicotinic acetylcholine receptors. It is used in the form of various salts as a ganglionic stimulant, a parasympathomimetic, and a vermifuge, especially in veterinary practice. It has been used as a euphoriant in the Pacific Islands.. arecoline : A tetrahydropyridine that is 1,2,5,6-tetrahydropyridine with a methyl group at position 1, and a methoxycarbonyl group at position 3. An alkaloid found in the areca nut, it acts as an agonist of muscarinic acetylcholine.	2.1	1	0	enoate ester; methyl ester; pyridine alkaloid; tetrahydropyridine	metabolite; muscarinic agonist
aspirin Aspirin: The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5). acetylsalicylate : A benzoate that is the conjugate base of acetylsalicylic acid, arising from deprotonation of the carboxy group.. acetylsalicylic acid : A member of the class of benzoic acids that is salicylic acid in which the hydrogen that is attached to the phenolic hydroxy group has been replaced by an acetoxy group. A non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity.	6.1	16	0	benzoic acids; phenyl acetates; salicylates	anticoagulant; antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; EC 1.1.1.188 (prostaglandin-F synthase) inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; plant activator; platelet aggregation inhibitor; prostaglandin antagonist; teratogenic agent
atenolol Atenolol: A cardioselective beta-1 adrenergic blocker possessing properties and potency similar to PROPRANOLOL, but without a negative inotropic effect.. atenolol : An ethanolamine compound having a (4-carbamoylmethylphenoxy)methyl group at the 1-position and an N-isopropyl substituent.	2.1	1	0	ethanolamines; monocarboxylic acid amide; propanolamine	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; environmental contaminant; sympatholytic agent; xenobiotic
azathioprine Azathioprine: An immunosuppressive agent used in combination with cyclophosphamide and hydroxychloroquine in the treatment of rheumatoid arthritis. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), this substance has been listed as a known carcinogen. (Merck Index, 11th ed). azathioprine : A thiopurine that is 6-mercaptopurine in which the mercapto hydrogen is replaced by a 1-methyl-4-nitroimidazol-5-yl group. It is a prodrug for mercaptopurine and is used as an immunosuppressant, prescribed for the treatment of inflammatory conditions and after organ transplantation and also for treatment of Crohn's didease and MS.	2.37	2	0	aryl sulfide; C-nitro compound; imidazoles; thiopurine	antimetabolite; antineoplastic agent; carcinogenic agent; DNA synthesis inhibitor; hepatotoxic agent; immunosuppressive agent; prodrug
azelastine azelastine: azeptin is azelastine hydrochloride; structure; eye drop formulation effective in relieving symptoms of allergic conjunctivitis; do not confuse with 5-loxin which is an extract of Boswellia. azelastine : A phthalazine compound having an oxo substituent at the 1-position, a 1-methylazepan-4-yl group at the 2-position and a 4-chlorobenzyl substituent at the 4-position.	2.1	1	0	monochlorobenzenes; phthalazines; tertiary amino compound	anti-allergic agent; anti-asthmatic drug; bronchodilator agent; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; H1-receptor antagonist; platelet aggregation inhibitor
baclofen [no description available]	1.98	1	0	amino acid zwitterion; gamma-amino acid; monocarboxylic acid; monochlorobenzenes; primary amino compound	central nervous system depressant; GABA agonist; muscle relaxant
2,2-bis(4-glycidyloxyphenyl)propane 2,2-bis(4-glycidyloxyphenyl)propane: structure	2.1	1	0	diarylmethane
bay-k-8644 3-Pyridinecarboxylic acid, 1,4-dihydro-2,6-dimethyl-5-nitro-4-(2-(trifluoromethyl)phenyl)-, Methyl ester: A dihydropyridine derivative, which, in contrast to NIFEDIPINE, functions as a calcium channel agonist. The compound facilitates Ca2+ influx through partially activated voltage-dependent Ca2+ channels, thereby causing vasoconstrictor and positive inotropic effects. It is used primarily as a research tool.. Bay-K-8644 : A racemate comprising equimolar amounts of (R)- and (S)-Bay-K-8644. methyl 2,6-dimethyl-5-nitro-4-[2-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3-carboxylate : A pentasubstituted dihydropyridine carrying methoxycarbonyl, 2-(trifluoromethyl)phenyl and nitro substituents at positions 3, 4 and 5 respectively as well as two methyl substituents at positions 2 and 6.	3.77	11	0	(trifluoromethyl)benzenes; C-nitro compound; dihydropyridine; methyl ester
benzo(a)pyrene Benzo(a)pyrene: A potent mutagen and carcinogen. It is a public health concern because of its possible effects on industrial workers, as an environmental pollutant, an as a component of tobacco smoke.. benzo[a]pyrene : An ortho- and peri-fused polycyclic arene consisting of five fused benzene rings.	2.94	4	0	ortho- and peri-fused polycyclic arene	carcinogenic agent; mouse metabolite
benzyl isothiocyanate benzyl isothiocyanate: inhibits carcinogen-induced neoplasia; structure in Negwer, 5th ed, #715; also promotes urinary bladder carcinoma	2.03	1	0	benzenes; isothiocyanate	antibacterial drug
bepridil Bepridil: A long-acting calcium-blocking agent with significant anti-anginal activity. The drug produces significant coronary vasodilation and modest peripheral effects. It has antihypertensive and selective anti-arrhythmia activities and acts as a calmodulin antagonist.. bepridil : A tertiary amine in which the substituents on nitrogen are benzyl, phenyl and 3-(2-methylpropoxy)-2-(pyrrolidin-1-yl)propyl.	5	9	0	pyrrolidines; tertiary amine	anti-arrhythmia drug; antihypertensive agent; calcium channel blocker; vasodilator agent
berberine [no description available]	8.17	5	0	alkaloid antibiotic; berberine alkaloid; botanical anti-fungal agent; organic heteropentacyclic compound	antilipemic drug; antineoplastic agent; antioxidant; EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor; EC 1.21.3.3 (reticuline oxidase) inhibitor; EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor; EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor; EC 2.7.11.10 (IkappaB kinase) inhibitor; EC 3.1.1.4 (phospholipase A2) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; geroprotector; hypoglycemic agent; metabolite; potassium channel blocker
diminazene Diminazene: An effective trypanocidal agent.. diminazene : A triazene derivative that is triazene in which each of the terminal nitrogens is substituted by a 4-carbamimidoylphenyl group.	2.21	1	0	carboxamidine; triazene derivative	antiparasitic agent; trypanocidal drug
beta-naphthoflavone beta-Naphthoflavone: A polyaromatic hydrocarbon inducer of P4501A1 and P4501A2 cytochromes. (Proc Soc Exp Biol Med 1994 Dec:207(3):302-308). beta-naphthoflavone : An extended flavonoid resulting from the formal fusion of a benzene ring with the f side of flavone.	3.1	1	0	extended flavonoid; naphtho-gamma-pyrone; organic heterotricyclic compound	aryl hydrocarbon receptor agonist
betaxolol [no description available]	2.1	1	0	propanolamine	antihypertensive agent; beta-adrenergic antagonist; sympatholytic agent
bethanechol Bethanechol: A slowly hydrolyzing muscarinic agonist with no nicotinic effects. Bethanechol is generally used to increase smooth muscle tone, as in the GI tract following abdominal surgery or in urinary retention in the absence of obstruction. It may cause hypotension, HEART RATE changes, and BRONCHIAL SPASM.. bethanechol : The carbamic acid ester of 2-methylcholine. A slowly hydrolysed muscarinic agonist with no nicotinic effects, it is used as its chloride salt to increase smooth muscle tone, as in the gastrointestinal tract following abdominal surgery, treatment of gastro-oesophageal reflux disease, and as an alternative to catheterisation in the treatment of non-obstructive urinary retention.	1.98	1	0	carbamate ester; quaternary ammonium ion	muscarinic agonist
2,5-di-tert-butylhydroquinone 2,5-di-tert-butylbenzene-1,4-diol : A member of the class of hydroquinones that is benzene-1,4-diol substituted by tert-butyl groups at position 2 and 5.	2.9	4	0	hydroquinones
bisbenzimidazole Bisbenzimidazole: A benzimidazole antifilarial agent; it is fluorescent when it binds to certain nucleotides in DNA, thus providing a tool for the study of DNA replication; it also interferes with mitosis.	2.44	2	0	bibenzimidazole; N-methylpiperazine	anthelminthic drug; fluorochrome
bisindolylmaleimide i bisindolylmaleimide I: a bis(indolyl)maleimide	2.41	2	0
bisoprolol Bisoprolol: A cardioselective beta-1 adrenergic blocker. It is effective in the management of HYPERTENSION and ANGINA PECTORIS.	2.1	1	0	secondary alcohol; secondary amine	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; sympatholytic agent
bufexamac Bufexamac: A benzeneacetamide with anti-inflammatory, analgesic, and antipyretic action. It is administered topically, orally, or rectally.. bufexamac : A hydroxamic acid derived from phenylacetamide in which the benzene moiety is substituted at C-4 by a butoxy group. It has anti-inflammatory, analgesic, and antipyretic properties.	2.01	1	0	aromatic ether; hydroxamic acid	antipyretic; non-narcotic analgesic; non-steroidal anti-inflammatory drug
bumetanide [no description available]	4.2	5	0	amino acid; benzoic acids; sulfonamide	diuretic; EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor
buspirone Buspirone: An anxiolytic agent and serotonin receptor agonist belonging to the azaspirodecanedione class of compounds. Its structure is unrelated to those of the BENZODIAZAPINES, but it has an efficacy comparable to DIAZEPAM.. buspirone : An azaspiro compound that is 8-azaspiro[4.5]decane-7,9-dione substituted at the nitrogen atom by a 4-(piperazin-1-yl)butyl group which in turn is substituted by a pyrimidin-2-yl group at the N(4) position.	2.5	2	0	azaspiro compound; N-alkylpiperazine; N-arylpiperazine; organic heteropolycyclic compound; piperidones; pyrimidines	anxiolytic drug; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; sedative; serotonergic agonist
caffeine [no description available]	8.12	73	1	purine alkaloid; trimethylxanthine	adenosine A2A receptor antagonist; adenosine receptor antagonist; adjuvant; central nervous system stimulant; diuretic; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; environmental contaminant; food additive; fungal metabolite; geroprotector; human blood serum metabolite; mouse metabolite; mutagen; plant metabolite; psychotropic drug; ryanodine receptor agonist; xenobiotic
verapamil Verapamil: A calcium channel blocker that is a class IV anti-arrhythmia agent.. verapamil : A racemate comprising equimolar amounts of dexverapamil and (S)-verapamil. An L-type calcium channel blocker of the phenylalkylamine class, it is used (particularly as the hydrochloride salt) in the treatment of hypertension, angina pectoris and cardiac arrhythmia, and as a preventive medication for migraine.. 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile : A tertiary amino compound that is 3,4-dimethoxyphenylethylamine in which the hydrogens attached to the nitrogen are replaced by a methyl group and a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.	5.67	80	0	aromatic ether; nitrile; polyether; tertiary amino compound
calmidazolium calmidazolium: powerful inhibitor of or red blood cell Ca++-ATPase & Ca++ transport into inside-out red blood cell vesicles; RN refers to chloride; structure in first source; an antagonist of calmodulin. calmidazolium : An imidazolium ion that is imidazolium cation substituted by a bis(4-chlorophenyl)methyl group at position 1 and a 2-[(2,4-dichlorobenzyl)oxy]-2-(2,4-dichlorophenyl)ethyl group at position 3. It acts as an antagonist of calmodulin, a calcium binding messenger protein.	4.05	15	0	imidazolium ion	apoptosis inducer; calmodulin antagonist
camphor, (+-)-isomer [no description available]	2.1	1	0	bornane monoterpenoid; cyclic monoterpene ketone	plant metabolite
candesartan candesartan: a nonpeptide angiotensin II receptor antagonist. candesartan : A benzimidazolecarboxylic acid that is 1H-benzimidazole-7-carboxylic acid substituted by an ethoxy group at position 2 and a ({2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl}methyl) group at position 1. It is a angiotensin receptor antagonist used for the treatment of hypertension.	2.02	1	0	benzimidazolecarboxylic acid; biphenylyltetrazole	angiotensin receptor antagonist; antihypertensive agent; environmental contaminant; xenobiotic
carbamazepine Carbamazepine: A dibenzazepine that acts as a sodium channel blocker. It is used as an anticonvulsant for the treatment of grand mal and psychomotor or focal SEIZURES. It may also be used in the management of BIPOLAR DISORDER, and has analgesic properties.. carbamazepine : A dibenzoazepine that is 5H-dibenzo[b,f]azepine carrying a carbamoyl substituent at the azepine nitrogen, used as an anticonvulsant.	4.06	2	0	dibenzoazepine; ureas	analgesic; anticonvulsant; antimanic drug; drug allergen; EC 3.5.1.98 (histone deacetylase) inhibitor; environmental contaminant; glutamate transporter activator; mitogen; non-narcotic analgesic; sodium channel blocker; xenobiotic
carbidopa [no description available]	2.1	1	0	benzenes; monocarboxylic acid
carbofuran Carbofuran: A cholinesterase inhibitor that is used as a systemic insecticide, an acaricide, and nematocide. (From Merck Index, 11th ed)	2.06	1	0	1-benzofurans; carbamate ester	acaricide; agrochemical; avicide; carbamate insecticide; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; nematicide
carvedilol [no description available]	2.1	1	0	carbazoles; secondary alcohol; secondary amino compound	alpha-adrenergic antagonist; antihypertensive agent; beta-adrenergic antagonist; cardiovascular drug; vasodilator agent
carbonyl cyanide m-chlorophenyl hydrazone Carbonyl Cyanide m-Chlorophenyl Hydrazone: A proton ionophore. It is commonly used as an uncoupling agent and inhibitor of photosynthesis because of its effects on mitochondrial and chloroplast membranes.. CCCP : A member of the class of monochlorobenzenes that is benzene substituted by 2-(1,3-dinitrilopropan-2-ylidene)hydrazinyl and chloro groups at positions 1 and 3, respectively. It is a mitochondrial depolarizing agent that induces reactive oxygen species mediated cell death.	2.1	1	0	hydrazone; monochlorobenzenes; nitrile	antibacterial agent; geroprotector; ionophore
celecoxib [no description available]	7.31	1	0	organofluorine compound; pyrazoles; sulfonamide; toluenes	cyclooxygenase 2 inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug
celiprolol Celiprolol: A cardioselective beta-1 adrenergic antagonist that has intrinsic sympathomimetic activity. It is used in the management of ANGINA PECTORIS and HYPERTENSION.	2.1	1	0	aromatic ketone
cetyltrimethylammonium ion Cetrimonium: Cetyltrimethylammonium compound whose salts and derivatives are used primarily as topical antiseptics.. cetyltrimethylammonium ion : A quaternary ammonium ion in which the substituents on nitrogen are one hexadecyl and three methyl groups.	2.21	1	0	quaternary ammonium ion
cetyl alcohol cetyl alcohol: has been used for eczema, skin irritations; RN given refers to parent cpd; structure. hexadecanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of sixteen carbon atoms.. hexadecan-1-ol : A long-chain primary fatty alcohol that is hexadecane substituted by a hydroxy group at position 1.	2.06	1	0	hexadecanol; long-chain primary fatty alcohol	algal metabolite; flavouring agent; human metabolite; plant metabolite
cetylpyridinium Cetylpyridinium: Cationic bactericidal surfactant used as a topical antiseptic for skin, wounds, mucous membranes, instruments, etc.; and also as a component in mouthwash and lozenges.	1.94	1	0	pyridinium ion
chelerythrine chelerythrine : A benzophenanthridine alkaloid isolated from the root of Zanthoxylum simulans, Chelidonium majus L., and other Papaveraceae.	2.42	2	0	benzophenanthridine alkaloid; organic cation	antibacterial agent; antineoplastic agent; EC 2.7.11.13 (protein kinase C) inhibitor
chloroquine Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.	3.1	5	0	aminoquinoline; organochlorine compound; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; antirheumatic drug; autophagy inhibitor; dermatologic drug
chlorpheniramine Chlorpheniramine: A histamine H1 antagonist used in allergic reactions, hay fever, rhinitis, urticaria, and asthma. It has also been used in veterinary applications. One of the most widely used of the classical antihistaminics, it generally causes less drowsiness and sedation than PROMETHAZINE.. chlorphenamine : A tertiary amino compound that is propylamine which is substituted at position 3 by a pyridin-2-yl group and a p-chlorophenyl group and in which the hydrogens attached to the nitrogen are replaced by methyl groups. A histamine H1 antagonist, it is used to relieve the symptoms of hay fever, rhinitis, urticaria, and asthma.	3.54	2	0	monochlorobenzenes; pyridines; tertiary amino compound	anti-allergic agent; antidepressant; antipruritic drug; H1-receptor antagonist; histamine antagonist; serotonin uptake inhibitor
chlorpromazine Chlorpromazine: The prototypical phenothiazine antipsychotic drug. Like the other drugs in this class chlorpromazine's antipsychotic actions are thought to be due to long-term adaptation by the brain to blocking DOPAMINE RECEPTORS. Chlorpromazine has several other actions and therapeutic uses, including as an antiemetic and in the treatment of intractable hiccup.. chlorpromazine : A substituted phenothiazine in which the ring nitrogen at position 10 is attached to C-3 of an N,N-dimethylpropanamine moiety.	5.08	14	0	organochlorine compound; phenothiazines; tertiary amine	anticoronaviral agent; antiemetic; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; phenothiazine antipsychotic drug
chlorpyrifos Chlorpyrifos: An organothiophosphate cholinesterase inhibitor that is used as an insecticide and as an acaricide.. chlorpyrifos : An organic thiophosphate that is O,O-diethyl hydrogen phosphorothioate in which the hydrogen of the hydroxy group has been replaced by a 3,5,6-trichloropyridin-2-yl group.	2.25	1	0	chloropyridine; organic thiophosphate	acaricide; agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; environmental contaminant; insecticide; xenobiotic
cilostamide cilostamide: selective inhibitor of cyclic AMP phosphodiesterase & platelet aggregation; structure	1.98	1	0	quinolines
cimetidine Cimetidine: A histamine congener, it competitively inhibits HISTAMINE binding to HISTAMINE H2 RECEPTORS. Cimetidine has a range of pharmacological actions. It inhibits GASTRIC ACID secretion, as well as PEPSIN and GASTRIN output.. cimetidine : A member of the class of guanidines that consists of guanidine carrying a methyl substituent at position 1, a cyano group at position 2 and a 2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl group at position 3. It is a H2-receptor antagonist that inhibits the production of acid in stomach.	2.1	1	0	aliphatic sulfide; guanidines; imidazoles; nitrile	adjuvant; analgesic; anti-ulcer drug; H2-receptor antagonist; P450 inhibitor
eucalyptol [no description available]	4.27	5	0
cinoxacin Cinoxacin: Synthetic antimicrobial related to OXOLINIC ACID and NALIDIXIC ACID and used in URINARY TRACT INFECTIONS.. cinoxacin : A member of the class of cinnolines that is 6,7-methylenedioxycinnolin-4(1H)-one bearing an ethyl group at position 1 and a carboxylic acid group at position 3. An analogue of oxolinic acid, it has similar antibacterial actions. It was formerly used for the treatment of urinary tract infections.	2.1	1	0	cinnolines; oxacycle; oxo carboxylic acid	antibacterial drug; antiinfective agent
ciprofibrate [no description available]	3.1	1	0	cyclopropanes; monocarboxylic acid; organochlorine compound	antilipemic drug
ciprofloxacin Ciprofloxacin: A broad-spectrum antimicrobial carboxyfluoroquinoline.. ciprofloxacin : A quinolone that is quinolin-4(1H)-one bearing cyclopropyl, carboxylic acid, fluoro and piperazin-1-yl substituents at positions 1, 3, 6 and 7, respectively.	3.01	4	0	aminoquinoline; cyclopropanes; fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone; zwitterion	antibacterial drug; antiinfective agent; antimicrobial agent; DNA synthesis inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; environmental contaminant; topoisomerase IV inhibitor; xenobiotic
citalopram Citalopram: A furancarbonitrile that is one of the serotonin uptake inhibitors used as an antidepressant. The drug is also effective in reducing ethanol uptake in alcoholics and is used in depressed patients who also suffer from TARDIVE DYSKINESIA in preference to tricyclic antidepressants, which aggravate dyskinesia.. citalopram : A racemate comprising equimolar amounts of (R)-citalopram and its enantiomer, escitalopram. It is used as an antidepressant, although only escitalopram is active.. 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile : A nitrile that is 1,3-dihydro-2-benzofuran-5-carbonitrile in which one of the hydrogens at position 1 is replaced by a p-fluorophenyl group, while the other is replaced by a 3-(dimethylamino)propyl group.	2.1	1	0	2-benzofurans; cyclic ether; nitrile; organofluorine compound; tertiary amino compound
clenbuterol Clenbuterol: A substituted phenylaminoethanol that has beta-2 adrenomimetic properties at very low doses. It is used as a bronchodilator in asthma.. clenbuterol : A substituted aniline that is 2,6-dichloroaniline in which the hydrogen at position 4 has been replaced by a 2-(tert-butylamino)-1-hydroxyethyl group.	2.41	1	0	amino alcohol; dichlorobenzene; ethanolamines; primary arylamine; secondary amino compound; substituted aniline	beta-adrenergic agonist; bronchodilator agent; sympathomimetic agent
clofibrate angiokapsul: contains clofibrate & insoitolnicotinate	3.47	2	0	aromatic ether; ethyl ester; monochlorobenzenes	anticholesteremic drug; antilipemic drug; geroprotector; PPARalpha agonist
clofibric acid Clofibric Acid: An antilipemic agent that is the biologically active metabolite of CLOFIBRATE.. clofibric acid : A monocarboxylic acid that is isobutyric acid substituted at position 2 by a p-chlorophenoxy group. It is a metabolite of the drug clofibrate.	3.1	1	0	aromatic ether; monocarboxylic acid; monochlorobenzenes	anticholesteremic drug; antilipemic drug; antineoplastic agent; herbicide; marine xenobiotic metabolite; PPARalpha agonist
clomipramine Clomipramine: A tricyclic antidepressant similar to IMIPRAMINE that selectively inhibits the uptake of serotonin in the brain. It is readily absorbed from the gastrointestinal tract and demethylated in the liver to form its primary active metabolite, desmethylclomipramine.. clomipramine : A dibenzoazepine that is 10,11-dihydro-5H-dibenzo[b,f]azepine which is substituted by chlorine at position 3 and in which the hydrogen attached to the nitrogen is replaced by a 3-(dimethylamino)propyl group. One of the more sedating tricyclic antidepressants, it is used as the hydrochloride salt for the treatment of depression as well as obsessive-compulsive disorder and phobias.	2.1	1	0	dibenzoazepine	anticoronaviral agent; antidepressant; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor; serotonergic antagonist; serotonergic drug; serotonin uptake inhibitor
clonidine Clonidine: An imidazoline sympatholytic agent that stimulates ALPHA-2 ADRENERGIC RECEPTORS and central IMIDAZOLINE RECEPTORS. It is commonly used in the management of HYPERTENSION.. clonidine (amino form) : A clonidine that is 4,5-dihydro-1H-imidazol-2-amine in which one of the amino hydrogens is replaced by a 2,6-dichlorophenyl group.	2.69	3	0	clonidine; imidazoline
4-chloro-N-(2,6-dimethyl-1-piperidinyl)-3-sulfamoylbenzamide [no description available]	3.1	1	0	sulfonamide
clotrimazole [no description available]	2.02	1	0	conazole antifungal drug; imidazole antifungal drug; imidazoles; monochlorobenzenes	antiinfective agent; environmental contaminant; xenobiotic
4-cresol 4-cresol: RN given refers to parent cpd. p-cresol : A cresol that consists of toluene substituted by a hydroxy group at position 4. It is a metabolite of aromatic amino acid metabolism produced by intestinal microflora in humans and animals.	4.06	2	0	cresol	Escherichia coli metabolite; human metabolite; uremic toxin
cyclobenzaprine cyclobenzaprine: RN given refers to parent cpd; Lisseril is synonymous for HCl; structure. cyclobenzaprine : 5-Methylidene-5H-dibenzo[a,d]cycloheptene in which one of the hydrogens of the methylidene group is substituted by a 2-(dimethylamino)ethyl group. A centrally acting skeletal muscle relaxant, it is used as its hydrochloride salt in the symptomatic treatment of painful muscle spasm.	2.1	1	0	carbotricyclic compound	antidepressant; muscle relaxant; tranquilizing drug
cycloleucine Cycloleucine: An amino acid formed by cyclization of leucine. It has cytostatic, immunosuppressive and antineoplastic activities.. 1-aminocyclopentanecarboxylic acid : A non-proteinogenic alpha-amino acid that is cyclopentane substituted at position 1 by amino and carboxy groups.	2	1	0	non-proteinogenic alpha-amino acid	EC 2.5.1.6 (methionine adenosyltransferase) inhibitor
cyproheptadine Cyproheptadine: A serotonin antagonist and a histamine H1 blocker used as antipruritic, appetite stimulant, antiallergic, and for the post-gastrectomy dumping syndrome, etc.. cyproheptadine : The product resulting from the formal oxidative coupling of position 5 of 5H-dibenzo[a,d]cycloheptene with position 4 of 1-methylpiperidine resulting in the formation of a double bond between the two fragments. It is a sedating antihistamine with antimuscarinic and calcium-channel blocking actions. It is used (particularly as the hydrochloride sesquihydrate) for the relief of allergic conditions including rhinitis, conjunctivitis due to inhalant allergens and foods, urticaria and angioedema, and in pruritic skin disorders. Unlike other antihistamines, it is also a seratonin receptor antagonist, making it useful in conditions such as vascular headache and anorexia.	3.1	1	0	piperidines; tertiary amine	anti-allergic agent; antipruritic drug; gastrointestinal drug; H1-receptor antagonist; serotonergic antagonist
cystamine [no description available]	2.35	2	0	organic disulfide; primary amino compound	EC 2.3.2.13 (protein-glutamine gamma-glutamyltransferase) inhibitor
danthron danthron: structure. chrysazin : A dihydroxyanthraquinone that is anthracene-9,10-dione substituted by hydroxy groups at positions 1 and 8.	3.54	2	0	dihydroxyanthraquinone	apoptosis inducer; plant metabolite
dantrolene Dantrolene: Skeletal muscle relaxant that acts by interfering with excitation-contraction coupling in the muscle fiber. It is used in spasticity and other neuromuscular abnormalities. Although the mechanism of action is probably not central, dantrolene is usually grouped with the central muscle relaxants.. dantrolene : The hydrazone resulting from the formal condensation of 5-(4-nitrophenyl)furfural with 1-aminohydantoin. A ryanodine receptor antagonist used for the relief of chronic severe spasticity and malignant hyperthermia.	5.32	18	0	hydrazone; imidazolidine-2,4-dione	muscle relaxant; neuroprotective agent; ryanodine receptor antagonist
dapsone [no description available]	3.1	1	0	substituted aniline; sulfone	anti-inflammatory drug; antiinfective agent; antimalarial; leprostatic drug
decanoic acid decanoate : A fatty acid anion 10:0 that is the conjugate base of decanoic acid.. decanoic acid : A C10, straight-chain saturated fatty acid.	3.1	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; anti-inflammatory agent; antibacterial agent; human metabolite; plant metabolite; volatile oil component
deferoxamine Deferoxamine: Natural product isolated from Streptomyces pilosus. It forms iron complexes and is used as a chelating agent, particularly in the mesylate form.. desferrioxamine B : An acyclic desferrioxamine that is butanedioic acid in which one of the carboxy groups undergoes formal condensation with the primary amino group of N-(5-aminopentyl)-N-hydroxyacetamide and the second carboxy group undergoes formal condensation with the hydroxyamino group of N(1)-(5-aminopentyl)-N(1)-hydroxy-N(4)-[5-(hydroxyamino)pentyl]butanediamide. It is a siderophore native to Streptomyces pilosus biosynthesised by the DesABCD enzyme cluster as a high affinity Fe(III) chelator.	3.41	7	0	acyclic desferrioxamine	bacterial metabolite; ferroptosis inhibitor; iron chelator; siderophore
dephostatin dephostatin: from Streptomyces sp. MJ742-NF5; structure given in first source	2.25	1	0
desipramine Desipramine: A tricyclic dibenzazepine compound that potentiates neurotransmission. Desipramine selectively blocks reuptake of norepinephrine from the neural synapse, and also appears to impair serotonin transport. This compound also possesses minor anticholinergic activity, through its affinity to muscarinic receptors.. desipramine : A dibenzoazepine consisting of 10,11-dihydro-5H-dibenzo[b,f]azepine substituted on nitrogen with a 3-(methylamino)propyl group.	4.05	4	0	dibenzoazepine; secondary amino compound	adrenergic uptake inhibitor; alpha-adrenergic antagonist; antidepressant; cholinergic antagonist; drug allergen; EC 3.1.4.12 (sphingomyelin phosphodiesterase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; H1-receptor antagonist; serotonin uptake inhibitor
diazepam Diazepam: A benzodiazepine with anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties and a long duration of action. Its actions are mediated by enhancement of GAMMA-AMINOBUTYRIC ACID activity.. diazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a methyl group at position 1 and a phenyl group at position 5.	2.69	3	0	1,4-benzodiazepinone; organochlorine compound	anticonvulsant; anxiolytic drug; environmental contaminant; sedative; xenobiotic
diazoxide Diazoxide: A benzothiadiazine derivative that is a peripheral vasodilator used for hypertensive emergencies. It lacks diuretic effect, apparently because it lacks a sulfonamide group.. diazoxide : A benzothiadiazine that is the S,S-dioxide of 2H-1,2,4-benzothiadiazine which is substituted at position 3 by a methyl group and at position 7 by chlorine. A peripheral vasodilator, it increases the concentration of glucose in the plasma and inhibits the secretion of insulin by the beta- cells of the pancreas. It is used orally in the management of intractable hypoglycaemia and intravenously in the management of hypertensive emergencies.	2.37	2	0	benzothiadiazine; organochlorine compound; sulfone	antihypertensive agent; beta-adrenergic agonist; bronchodilator agent; cardiotonic drug; diuretic; K-ATP channel agonist; sodium channel blocker; sympathomimetic agent; vasodilator agent
dibucaine Dibucaine: A local anesthetic of the amide type now generally used for surface anesthesia. It is one of the most potent and toxic of the long-acting local anesthetics and its parenteral use is restricted to spinal anesthesia. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1006). cinchocaine : A monocarboxylic acid amide that is the 2-(diethylamino)ethyl amide of 2-butoxyquinoline-4-carboxylic acid. One of the most potent and toxic of the long-acting local anesthetics, its parenteral use was restricted to spinal anesthesia. It is now generally only used (usually as the hydrochloride) in creams and ointments and in suppositories for temporary relief of pain and itching associated with skin and anorectal conditions.	1.98	1	0	aromatic ether; monocarboxylic acid amide; tertiary amino compound	topical anaesthetic
diclofenac Diclofenac: A non-steroidal anti-inflammatory agent (NSAID) with antipyretic and analgesic actions. It is primarily available as the sodium salt.. diclofenac : A monocarboxylic acid consisting of phenylacetic acid having a (2,6-dichlorophenyl)amino group at the 2-position.	3.31	5	0	amino acid; aromatic amine; dichlorobenzene; monocarboxylic acid; secondary amino compound	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
ddt 1,1-bis(p-chlorophenyl)-2,2,2-trichloroethane: structure in first source	1.96	1	0	benzenoid aromatic compound; chlorophenylethane; monochlorobenzenes; organochlorine insecticide	bridged diphenyl acaricide; carcinogenic agent; endocrine disruptor; persistent organic pollutant
pentetic acid Pentetic Acid: An iron chelating agent with properties like EDETIC ACID. DTPA has also been used as a chelator for other metals, such as plutonium.	2.69	3	0	pentacarboxylic acid	copper chelator
diflunisal Diflunisal: A salicylate derivative and anti-inflammatory analgesic with actions and side effects similar to those of ASPIRIN.. diflunisal : An organofluorine compound comprising salicylic acid having a 2,4-difluorophenyl group at the 5-position.	3.54	2	0	monohydroxybenzoic acid; organofluorine compound	non-narcotic analgesic; non-steroidal anti-inflammatory drug
dimercaprol Dimercaprol: An anti-gas warfare agent that is effective against Lewisite (dichloro(2-chlorovinyl)arsine) and formerly known as British Anti-Lewisite or BAL. It acts as a chelating agent and is used in the treatment of arsenic, gold, and other heavy metal poisoning.. dimercaprol : A dithiol that is propane-1,2-dithiol in which one of the methyl hydrogens is replaced by a hydroxy group. a chelating agent originally developed during World War II as an experimental antidote against the arsenic-based poison gas Lewisite, it has been used clinically since 1949 for the treatment of poisoning by arsenic, mercury and gold. It can also be used for treatment of poisoning by antimony, bismuth and possibly thallium, and (with sodium calcium edetate) in cases of acute leaad poisoning. Administration is by (painful) intramuscular injection of a suspension of dimercaprol in peanut oil, typically every 4 hours for 2-10 days depending on the toxicity. In the past, dimercaprol was also used for the treatment of Wilson's disease, a severely debilitating genetic disorder in which the body tends to retain copper, with resultant liver and brain injury.	2.38	2	0	dithiol; primary alcohol	chelator
diphenhydramine Diphenhydramine: A histamine H1 antagonist used as an antiemetic, antitussive, for dermatoses and pruritus, for hypersensitivity reactions, as a hypnotic, an antiparkinson, and as an ingredient in common cold preparations. It has some undesired antimuscarinic and sedative effects.. diphenhydramine : An ether that is the benzhydryl ether of 2-(dimethylamino)ethanol. It is a H1-receptor antagonist used as a antipruritic and antitussive drug.. antitussive : An agent that suppresses cough. Antitussives have a central or a peripheral action on the cough reflex, or a combination of both. Compare with expectorants, which are considered to increase the volume of secretions in the respiratory tract, so facilitating their removal by ciliary action and coughing, and mucolytics, which decrease the viscosity of mucus, facilitating its removal by ciliary action and expectoration.	3.84	3	0	ether; tertiary amino compound	anti-allergic agent; antidyskinesia agent; antiemetic; antiparkinson drug; antipruritic drug; antitussive; H1-receptor antagonist; local anaesthetic; muscarinic antagonist; oneirogen; sedative
diphenyleneiodonium diphenyleneiodonium: structure in first source; NADPH oxidase inhibitor. dibenziodolium : An organic cation that is fluorene in which the methylene group is replaced by a positively charged iodine.	2.04	1	0	organic cation
benzophenone benzophenone : The simplest member of the class of benzophenones, being formaldehyde in which both hydrogens are replaced by phenyl groups.	2.11	1	0	benzophenones	photosensitizing agent; plant metabolite
dipyridamole Dipyridamole: A phosphodiesterase inhibitor that blocks uptake and metabolism of adenosine by erythrocytes and vascular endothelial cells. Dipyridamole also potentiates the antiaggregating action of prostacyclin. (From AMA Drug Evaluations Annual, 1994, p752). dipyridamole : A pyrimidopyrimidine that is 2,2',2'',2'''-(pyrimido[5,4-d]pyrimidine-2,6-diyldinitrilo)tetraethanol substituted by piperidin-1-yl groups at positions 4 and 8 respectively. A vasodilator agent, it inhibits the formation of blood clots.	1.94	1	0	piperidines; pyrimidopyrimidine; tertiary amino compound; tetrol	adenosine phosphodiesterase inhibitor; EC 3.5.4.4 (adenosine deaminase) inhibitor; platelet aggregation inhibitor; vasodilator agent
disopyramide Disopyramide: A class I anti-arrhythmic agent (one that interferes directly with the depolarization of the cardiac membrane and thus serves as a membrane-stabilizing agent) with a depressant action on the heart similar to that of guanidine. It also possesses some anticholinergic and local anesthetic properties.. disopyramide : A monocarboxylic acid amide that is butanamide substituted by a diisopropylamino group at position 4, a phenyl group at position 2 and a pyridin-2-yl group at position 2. It is used as a anti-arrhythmia drug.	2.1	1	0	monocarboxylic acid amide; pyridines; tertiary amino compound	anti-arrhythmia drug
disulfiram [no description available]	2.37	2	0	organic disulfide; organosulfur acaricide	angiogenesis inhibitor; antineoplastic agent; apoptosis inducer; EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor; EC 3.1.1.1 (carboxylesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 5.99.1.2 (DNA topoisomerase) inhibitor; ferroptosis inducer; fungicide; NF-kappaB inhibitor
valproic acid Valproic Acid: A fatty acid with anticonvulsant and anti-manic properties that is used in the treatment of EPILEPSY and BIPOLAR DISORDER. The mechanisms of its therapeutic actions are not well understood. It may act by increasing GAMMA-AMINOBUTYRIC ACID levels in the brain or by altering the properties of VOLTAGE-GATED SODIUM CHANNELS.. valproic acid : A branched-chain saturated fatty acid that comprises of a propyl substituent on a pentanoic acid stem.	3.9	3	0	branched-chain fatty acid; branched-chain saturated fatty acid	anticonvulsant; antimanic drug; EC 3.5.1.98 (histone deacetylase) inhibitor; GABA agent; neuroprotective agent; psychotropic drug; teratogenic agent
domperidone Domperidone: A specific blocker of dopamine receptors. It speeds gastrointestinal peristalsis, causes prolactin release, and is used as antiemetic and tool in the study of dopaminergic mechanisms.. domperidone : 1-[3-(Piperidin-1-yl)propyl]-1,3-dihydro-2H-benzimidazol-2-one in which the 4-position of the piperidine ring is substituted by a 5-chloro-1,3-dihydro-2H-benzimidazol-2-on-1-yl group. A dopamine antagonist, it is used as an antiemetic for the short-term treatment of nausea and vomiting, and to control gastrointestinal effects of dopaminergic drugs given in the management of parkinsonism. The free base is used in oral suspensions, while the maleate salt is used in tablet preparations.	2.1	1	0	benzimidazoles; heteroarylpiperidine	antiemetic; dopaminergic antagonist
donepezil Donepezil: An indan and piperidine derivative that acts as a selective and reversible inhibitor of ACETYLCHOLINESTERASE. Donepezil is highly selective for the central nervous system and is used in the management of mild to moderate DEMENTIA in ALZHEIMER DISEASE.. donepezil : A racemate comprising equimolar amounts of (R)- and (S)-donepezil. A centrally acting reversible acetylcholinesterase inhibitor, its main therapeutic use is in the treatment of Alzheimer's disease where it is used to increase cortical acetylcholine.. 2-[(1-benzylpiperidin-4-yl)methyl]-5,6-dimethoxyindan-1-one : A member of the class of indanones that is 5,6-dimethoxyindan-1-one which is substituted at position 2 by an (N-benzylpiperidin-4-yl)methyl group.	2.54	2	0	aromatic ether; indanones; piperidines; racemate	EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; nootropic agent
doxepin Doxepin: A dibenzoxepin tricyclic compound. It displays a range of pharmacological actions including maintaining adrenergic innervation. Its mechanism of action is not fully understood, but it appears to block reuptake of monoaminergic neurotransmitters into presynaptic terminals. It also possesses anticholinergic activity and modulates antagonism of histamine H(1)- and H(2)-receptors.. doxepin : A dibenzooxepine that is 6,11-dihydrodibenzo[b,e]oxepine substituted by a 3-(dimethylamino)propylidene group at position 11. It is used as an antidepressant drug.	3.1	1	0	dibenzooxepine; tertiary amino compound	antidepressant
doxylamine Doxylamine: Histamine H1 antagonist with pronounced sedative properties. It is used in allergies and as an antitussive, antiemetic, and hypnotic. Doxylamine has also been administered in veterinary applications and was formerly used in PARKINSONISM.	3.1	1	0	pyridines; tertiary amine	anti-allergic agent; antiemetic; antitussive; cholinergic antagonist; H1-receptor antagonist; histamine antagonist; sedative
droperidol Droperidol: A butyrophenone with general properties similar to those of HALOPERIDOL. It is used in conjunction with an opioid analgesic such as FENTANYL to maintain the patient in a calm state of neuroleptanalgesia with indifference to surroundings but still able to cooperate with the surgeon. It is also used as a premedicant, as an antiemetic, and for the control of agitation in acute psychoses. (From Martindale, The Extra Pharmacopoeia, 29th ed, p593). droperidol : An organofluorine compound that is haloperidol in which the hydroxy group has been eliminated with the introduction of a double bond in the piperidine ring, and the 4-chlorophenyl group has been replaced by a benzimidazol-2-on-1-yl group. It is used in the management of chemotherapy-induced nausea and vomiting, and in conjunction with an opioid analgesic such as fentanyl to maintain the patient in a calm state of neuroleptanalgesia with indifference to surroundings but still able to cooperate with the surgeon.	2.1	1	0	aromatic ketone; benzimidazoles; organofluorine compound	anaesthesia adjuvant; antiemetic; dopaminergic antagonist; first generation antipsychotic
dyclonine [no description available]	2.1	1	0	aromatic ketone; piperidines	topical anaesthetic
9-(2-hydroxy-3-nonyl)adenine 9-(2-hydroxy-3-nonyl)adenine: specific inhibitor of adenosine deaminase	1.96	1	0
embelin embelin: from Embelia fruit (Myrsinaceae). embelin : A member of the class of dihydroxy-1,4-benzoquinones that is 2,5-dihydroxy-1,4-benzoquinone which is substituted by an undecyl group at position 3. Isolated from Lysimachia punctata and Embelia ribes, it exhibits antimicrobial, antineoplastic and inhibitory activity towards hepatitis C protease.	7.6	1	0	dihydroxy-1,4-benzoquinones	antimicrobial agent; antineoplastic agent; hepatitis C protease inhibitor; plant metabolite
emodin Emodin: Purgative anthraquinone found in several plants, especially RHAMNUS PURSHIANA. It was formerly used as a laxative, but is now used mainly as a tool in toxicity studies.. emodin : A trihydroxyanthraquinone that is 9,10-anthraquinone which is substituted by hydroxy groups at positions 1, 3, and 8 and by a methyl group at position 6. It is present in the roots and barks of numerous plants (particularly rhubarb and buckthorn), moulds, and lichens. It is an active ingredient of various Chinese herbs.	5.54	12	0	trihydroxyanthraquinone	antineoplastic agent; laxative; plant metabolite; tyrosine kinase inhibitor
erythrosine Fluoresceins: A family of spiro(isobenzofuran-1(3H),9'-(9H)xanthen)-3-one derivatives. These are used as dyes, as indicators for various metals, and as fluorescent labels in immunoassays.	4.78	7	1
ethacrynic acid Ethacrynic Acid: A compound that inhibits symport of sodium, potassium, and chloride primarily in the ascending limb of Henle, but also in the proximal and distal tubules. This pharmacological action results in excretion of these ions, increased urinary output, and reduction in extracellular fluid. This compound has been classified as a loop or high ceiling diuretic.. etacrynic acid : An aromatic ether that is phenoxyacetic acid in which the phenyl ring is substituted by chlorines at positions 2 and 3, and by a 2-methylidenebutanoyl group at position 4. It is a loop diuretic used to treat high blood pressure resulting from diseases such as congestive heart failure, liver failure, and kidney failure. It is also a glutathione S-transferase (EC 2.5.1.18) inhibitor.	3.54	2	0	aromatic ether; aromatic ketone; dichlorobenzene; monocarboxylic acid	EC 2.5.1.18 (glutathione transferase) inhibitor; ion transport inhibitor; loop diuretic
ether Ether: A mobile, very volatile, highly flammable liquid used as an inhalation anesthetic and as a solvent for waxes, fats, oils, perfumes, alkaloids, and gums. It is mildly irritating to skin and mucous membranes.. ether : An organooxygen compound with formula ROR, where R is not hydrogen.. diethyl ether : An ether in which the oxygen atom is linked to two ethyl groups.	2.74	3	0	ether; volatile organic compound	inhalation anaesthetic; non-polar solvent; refrigerant
ethoxyquin Ethoxyquin: Antioxidant; also a post-harvest dip to prevent scald on apples and pears.. ethoxyquin : A quinoline that is 1,2-dihydroquinoline bearing three methyl substituents at position 2, 2 and 4 as well as an ethoxy substituent at position 6.	3.06	1	0	aromatic ether; quinolines	antifungal agrochemical; food antioxidant; genotoxin; geroprotector; herbicide; Hsp90 inhibitor; neuroprotective agent; UDP-glucuronosyltransferase activator
eicosapentaenoic acid ethyl ester [no description available]	2	1	0
famotidine Famotidine: A competitive histamine H2-receptor antagonist. Its main pharmacodynamic effect is the inhibition of gastric secretion.	7.1	1	0	1,3-thiazoles; guanidines; sulfonamide	anti-ulcer drug; H2-receptor antagonist; P450 inhibitor
carbonyl cyanide p-trifluoromethoxyphenylhydrazone Carbonyl Cyanide p-Trifluoromethoxyphenylhydrazone: A proton ionophore that is commonly used as an uncoupling agent in biochemical studies.. carbonyl cyanide p-trifluoromethoxyphenylhydrazone : A hydrazone that is hydrazonomalononitrile in which one of the hydrazine hydrogens is substituted by a p-trifluoromethoxyphenyl group.	2.7	3	0	aromatic ether; hydrazone; nitrile; organofluorine compound	ATP synthase inhibitor; geroprotector; ionophore
felodipine Felodipine: A dihydropyridine calcium antagonist with positive inotropic effects. It lowers blood pressure by reducing peripheral vascular resistance through a highly selective action on smooth muscle in arteriolar resistance vessels.. felodipine : The mixed (methyl, ethyl) diester of 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid. A calcium-channel blocker, it lowers blood pressure by reducing peripheral vascular resistance through a highly selective action on smooth muscle in arteriolar resistance vessels. It is used in the management of hypertension and angina pectoris.	1.96	1	0	dichlorobenzene; dihydropyridine; ethyl ester; methyl ester	anti-arrhythmia drug; antihypertensive agent; calcium channel blocker; vasodilator agent
fendiline Fendiline: Coronary vasodilator; inhibits calcium function in muscle cells in excitation-contraction coupling; proposed as antiarrhythmic and antianginal agents.	2.1	1	0	diarylmethane
fenoprofen Fenoprofen: A propionic acid derivative that is used as a non-steroidal anti-inflammatory agent.. fenoprofen : A monocarboxylic acid that is propanoic acid in which one of the hydrogens at position 2 is substituted by a 3-phenoxyphenyl group. A non-steroidal anti-inflammatory drug, the dihydrate form of the calcium salt is used for the management of mild to moderate pain and for the relief of pain and inflammation associated with disorders such as arthritis. It is pharmacologically similar to aspirin, but causes less gastrointestinal bleeding.	3.1	1	0	monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; non-narcotic analgesic; non-steroidal anti-inflammatory drug
berotek Fenoterol: A synthetic adrenergic beta-2 agonist that is used as a bronchodilator and tocolytic.. fenoterol : A member of the class resorcinols that is 5-(1-hydroxyethyl)benzene-1,3-diol in which one of the methyl hydrogens is replaced by a 1-(4-hydroxyphenyl)propan-2-amino group. A beta2-adrenergic agonist, it is used (as the hydrobromide salt) as a bronchodilator in the management of reversible airway obstruction.	3.1	1	0	resorcinols; secondary alcohol; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; sympathomimetic agent; tocolytic agent
fentanyl Fentanyl: A potent narcotic analgesic, abuse of which leads to habituation or addiction. It is primarily a mu-opioid agonist. Fentanyl is also used as an adjunct to general anesthetics, and as an anesthetic for induction and maintenance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1078). fentanyl : A monocarboxylic acid amide resulting from the formal condensation of the aryl amino group of N-phenyl-1-(2-phenylethyl)piperidin-4-amine with propanoic acid.	2.1	1	0	anilide; monocarboxylic acid amide; piperidines	adjuvant; anaesthesia adjuvant; anaesthetic; intravenous anaesthetic; mu-opioid receptor agonist; opioid analgesic
flecainide Flecainide: A potent anti-arrhythmia agent, effective in a wide range of ventricular and atrial ARRHYTHMIAS and TACHYCARDIAS.. flecainide : A monocarboxylic acid amide obtained by formal condensation of the carboxy group of 2,5-bis(2,2,2-trifluoroethoxy)benzoic acid with the primary amino group of piperidin-2-ylmethylamine. An antiarrhythmic agent used (in the form of its acetate salt) to prevent and treat tachyarrhythmia (abnormal fast rhythm of the heart).	2.1	1	0	aromatic ether; monocarboxylic acid amide; organofluorine compound; piperidines	anti-arrhythmia drug
fleroxacin Fleroxacin: A broad-spectrum antimicrobial fluoroquinolone. The drug strongly inhibits the DNA-supercoiling activity of DNA GYRASE.. fleroxacin : A fluoroquinolone antibiotic that is 4-oxo-1,4-dihydroquinoline which is substituted at positions 1, 3, 6, 7 and 8 by 2-fluoroethyl, carboxy, fluoro, 4-methylpiperazin-1-yl and fluoro groups, respectively. It is active against many Gram-positive and Gram-negative bacteria.	2.1	1	0	difluorobenzene; fluoroquinolone antibiotic; monocarboxylic acid; N-alkylpiperazine; quinolines	antibacterial drug; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; topoisomerase IV inhibitor
fluconazole Fluconazole: Triazole antifungal agent that is used to treat oropharyngeal CANDIDIASIS and cryptococcal MENINGITIS in AIDS.. fluconazole : A member of the class of triazoles that is propan-2-ol substituted at position 1 and 3 by 1H-1,2,4-triazol-1-yl groups and at position 2 by a 2,4-difluorophenyl group. It is an antifungal drug used for the treatment of mucosal candidiasis and for systemic infections including systemic candidiasis, coccidioidomycosis, and cryptococcosis.	2.57	2	0	conazole antifungal drug; difluorobenzene; tertiary alcohol; triazole antifungal drug	environmental contaminant; P450 inhibitor; xenobiotic
flufenamic acid Flufenamic Acid: An anthranilic acid derivative with analgesic, anti-inflammatory, and antipyretic properties. It is used in musculoskeletal and joint disorders and administered by mouth and topically. (From Martindale, The Extra Pharmacopoeia, 30th ed, p16). flufenamic acid : An aromatic amino acid consisting of anthranilic acid carrying an N-(trifluoromethyl)phenyl substituent. An analgesic and anti-inflammatory, it is used in rheumatic disorders.	2.44	2	0	aromatic amino acid; organofluorine compound	antipyretic; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
fluphenazine [no description available]	3.48	2	0	N-alkylpiperazine; organofluorine compound; phenothiazines	anticoronaviral agent; dopaminergic antagonist; phenothiazine antipsychotic drug
flumazenil Flumazenil: A potent benzodiazepine receptor antagonist. Since it reverses the sedative and other actions of benzodiazepines, it has been suggested as an antidote to benzodiazepine overdoses.. flumazenil : An organic heterotricyclic compound that is 5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine which is substituted at positions 3, 5, 6, and 8 by ethoxycarbonyl, methyl, oxo, and fluoro groups, respectively. It is used as an antidote to benzodiazepine overdose.	2.1	1	0	ethyl ester; imidazobenzodiazepine; organofluorine compound	antidote to benzodiazepine poisoning; GABA antagonist
flumequine flumequine: structure. flumequine : A racemate comprising equimolar amounts of R- and S-flumequine. A broad-spectrum antibiotic, formerly used in veterinary medicine for stock breeding and treatment of aquacultures.. 9-fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid : A member of the class of pyridoquinolines that is 1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline carrying additional carboxy, methyl and fluoro substituents at positions 2, 5 and 9 respectively.	2.1	1	0	3-oxo monocarboxylic acid; organofluorine compound; pyridoquinoline; quinolone antibiotic
fluorescite fluorescein (acid form) : A xanthene dye that is highly fluorescent and commonly used as a fluorescent tracer.	3.1	1	0	benzoic acids; cyclic ketone; hydroxy monocarboxylic acid; organic heterotricyclic compound; phenols; xanthene dye	fluorescent dye; radioopaque medium
fluorouracil Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.	2.48	2	0	nucleobase analogue; organofluorine compound	antimetabolite; antineoplastic agent; environmental contaminant; immunosuppressive agent; radiosensitizing agent; xenobiotic
fluoxetine Fluoxetine: The first highly specific serotonin uptake inhibitor. It is used as an antidepressant and often has a more acceptable side-effects profile than traditional antidepressants.. fluoxetine : A racemate comprising equimolar amounts of (R)- and (S)-fluoxetine. A selective serotonin reuptake inhibitor (SSRI), it is used (generally as the hydrochloride salt) for the treatment of depression (and the depressive phase of bipolar disorder), bullimia nervosa, and obsessive-compulsive disorder.. N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine : An aromatic ether consisting of 4-trifluoromethylphenol in which the hydrogen of the phenolic hydroxy group is replaced by a 3-(methylamino)-1-phenylpropyl group.	8.39	6	0	(trifluoromethyl)benzenes; aromatic ether; secondary amino compound
flurbiprofen Flurbiprofen: An anti-inflammatory analgesic and antipyretic of the phenylalkynoic acid series. It has been shown to reduce bone resorption in periodontal disease by inhibiting CARBONIC ANHYDRASE.. flurbiprofen : A monocarboxylic acid that is a 2-fluoro-[1,1'-biphenyl-4-yl] moiety linked to C-2 of propionic acid. A non-steroidal anti-inflammatory, analgesic and antipyretic, it is used as a pre-operative anti-miotic as well as orally for arthritis or dental pain.	2.1	1	0	fluorobiphenyl; monocarboxylic acid	antipyretic; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
fluspirilene Fluspirilene: A long-acting injectable antipsychotic agent used for chronic schizophrenia.	2.1	1	0	diarylmethane
foscarnet Foscarnet: An antiviral agent used in the treatment of cytomegalovirus retinitis. Foscarnet also shows activity against human herpesviruses and HIV.. phosphonoformic acid : Phosphoric acid in which one of the hydroxy groups is replaced by a carboxylic acid group. It is used as the trisodium salt as an antiviral agent in the treatment of cytomegalovirus retinitis (CMV retinitis, an inflamation of the retina that can lead to blindness) and as an alternative to ganciclovir for AIDS patients who require concurrent antiretroviral therapy but are unable to tolerate ganciclovir due to haematological toxicity.	1.98	1	0	carboxylic acid; one-carbon compound; phosphonic acids	antiviral drug; geroprotector; HIV-1 reverse transcriptase inhibitor; sodium-dependent Pi-transporter inhibitor
furosemide Furosemide: A benzoic-sulfonamide-furan. It is a diuretic with fast onset and short duration that is used for EDEMA and chronic RENAL INSUFFICIENCY.. furosemide : A chlorobenzoic acid that is 4-chlorobenzoic acid substituted by a (furan-2-ylmethyl)amino and a sulfamoyl group at position 2 and 5 respectively. It is a diuretic used in the treatment of congestive heart failure.	3.54	2	0	chlorobenzoic acid; furans; sulfonamide	environmental contaminant; loop diuretic; xenobiotic
gentamicin Gentamicins: A complex of closely related aminoglycosides obtained from MICROMONOSPORA purpurea and related species. They are broad-spectrum antibiotics, but may cause ear and kidney damage. They act to inhibit PROTEIN BIOSYNTHESIS.	7.73	3	0
2,5-dihydroxybenzoic acid 2,5-dihydroxybenzoic acid: RN given refers to parent cpd; a oxidative product of saligenin. 2,5-dihydroxybenzoic acid : A dihydroxybenzoic acid having the two hydroxy groups at the 2- and 5-positions.	5.9	18	0	dihydroxybenzoic acid	EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; fungal metabolite; human metabolite; MALDI matrix material; mouse metabolite
glyburide Glyburide: An antidiabetic sulfonylurea derivative with actions like those of chlorpropamide. glyburide : An N-sulfonylurea that is acetohexamide in which the acetyl group is replaced by a 2-(5-chloro-2-methoxybenzamido)ethyl group.	2.92	4	0	monochlorobenzenes; N-sulfonylurea	anti-arrhythmia drug; EC 2.7.1.33 (pantothenate kinase) inhibitor; EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor; hypoglycemic agent
gö6983 [no description available]	2.11	1	0	indoles; maleimides
go 6976 [no description available]	2.44	2	0	indolocarbazole; organic heterohexacyclic compound	EC 2.7.11.13 (protein kinase C) inhibitor
gossypol Gossypol: A dimeric sesquiterpene found in cottonseed (GOSSYPIUM). The (-) isomer is active as a male contraceptive (CONTRACEPTIVE AGENTS, MALE) whereas toxic symptoms are associated with the (+) isomer.	2	1	0
guaifenesin Guaifenesin: An expectorant that also has some muscle relaxing action. It is used in many cough preparations.	3.14	5	0	methoxybenzenes
guanidine Guanidine: A strong organic base existing primarily as guanidium ions at physiological pH. It is found in the urine as a normal product of protein metabolism. It is also used in laboratory research as a protein denaturant. (From Martindale, the Extra Pharmacopoeia, 30th ed and Merck Index, 12th ed) It is also used in the treatment of myasthenia and as a fluorescent probe in HPLC.. guanidine : An aminocarboxamidine, the parent compound of the guanidines.	2.69	2	0	carboxamidine; guanidines; one-carbon compound
bis(2-guanidinoethyl)disulfide bis(2-guanidinoethyl)disulfide: bifunctional cation; RN given refers to parent cpd; structure	2	1	0
n-(2-(methylamino)ethyl)-5-isoquinolinesulfonamide [no description available]	2.39	2	0	isoquinolines; sulfonamide
1-(5-isoquinolinesulfonyl)-2-methylpiperazine 1-(5-Isoquinolinesulfonyl)-2-Methylpiperazine: A specific protein kinase C inhibitor, which inhibits superoxide release from human neutrophils (PMN) stimulated with phorbol myristate acetate or synthetic diacylglycerol.. 1-(5-isoquinolinesulfonyl)-2-methylpiperazine : A member of the class of N-sulfonylpiperazines that is 2-methylpiperazine substituted at position 1 by a 5-isoquinolinesulfonyl group.	3.93	13	0	isoquinolines; N-sulfonylpiperazine	EC 2.7.11.13 (protein kinase C) inhibitor
n-(2-aminoethyl)-5-isoquinolinesulfonamide [no description available]	1.98	1	0
fasudil fasudil: intracellular calcium antagonist; structure in first source. fasudil : An isoquinoline substituted by a (1,4-diazepan-1-yl)sulfonyl group at position 5. It is a Rho-kinase inhibitor and its hydrochloride hydrate form is approved for the treatment of cerebral vasospasm and cerebral ischemia.	2.01	1	0	isoquinolines; N-sulfonyldiazepane	antihypertensive agent; calcium channel blocker; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; geroprotector; neuroprotective agent; nootropic agent; vasodilator agent
haloperidol Haloperidol: A phenyl-piperidinyl-butyrophenone that is used primarily to treat SCHIZOPHRENIA and other PSYCHOSES. It is also used in schizoaffective disorder, DELUSIONAL DISORDERS, ballism, and TOURETTE SYNDROME (a drug of choice) and occasionally as adjunctive therapy in INTELLECTUAL DISABILITY and the chorea of HUNTINGTON DISEASE. It is a potent antiemetic and is used in the treatment of intractable HICCUPS. (From AMA Drug Evaluations Annual, 1994, p279). haloperidol : A compound composed of a central piperidine structure with hydroxy and p-chlorophenyl substituents at position 4 and an N-linked p-fluorobutyrophenone moiety.	3.09	5	0	aromatic ketone; hydroxypiperidine; monochlorobenzenes; organofluorine compound; tertiary alcohol	antidyskinesia agent; antiemetic; dopaminergic antagonist; first generation antipsychotic; serotonergic antagonist
halothane [no description available]	1.97	1	0	haloalkane; organobromine compound; organochlorine compound; organofluorine compound	inhalation anaesthetic
harmaline Harmaline: A beta-carboline alkaloid isolated from seeds of PEGANUM.. harmaline : A harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7 and has been reduced across the 3,4 bond.	2.41	2	0	harmala alkaloid	oneirogen
hexachlorophene Hexachlorophene: A chlorinated bisphenol antiseptic with a bacteriostatic action against Gram-positive organisms, but much less effective against Gram-negative organisms. It is mainly used in soaps and creams and is an ingredient of various preparations used for skin disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p797). hexachlorophene : An organochlorine compound that is diphenylmethane in which each of the phenyl groups is substituted by chlorines at positions 2, 3, and 5, and by a hydroxy group at position 6. An antiseptic that is effective against Gram-positive organisms, it is used in soaps and creams for the treatment of various skin disorders. It is also used in agriculture as an acaricide and fungicide, but is not approved for such use within the European Union.	2.46	2	0	bridged diphenyl fungicide; polyphenol; trichlorobenzene	acaricide; antibacterial agent; antifungal agrochemical; antiseptic drug
miltefosine miltefosine: hexadecyl phosphocholine derivative of cisplatin; did not substantially activate HIV long terminal repeat; less toxic than cisplatin. miltefosine : A phospholipid that is the hexadecyl monoester of phosphocholine.	2.44	2	0	phosphocholines; phospholipid	anti-inflammatory agent; anticoronaviral agent; antifungal agent; antineoplastic agent; antiprotozoal drug; apoptosis inducer; immunomodulator; protein kinase inhibitor
hexamethonium Hexamethonium: A nicotinic cholinergic antagonist often referred to as the prototypical ganglionic blocker. It is poorly absorbed from the gastrointestinal tract and does not cross the blood-brain barrier. It has been used for a variety of therapeutic purposes including hypertension but, like the other ganglionic blockers, it has been replaced by more specific drugs for most purposes, although it is widely used a research tool.	2.39	2	0	quaternary ammonium salt
hexobarbital Hexobarbital: A barbiturate that is effective as a hypnotic and sedative.. hexobarbital : A member of the class of barbiturates taht is barbituric acid substituted at N-1 by methyl and at C-5 by methyl and cyclohex-1-enyl groups.	2.37	2	0	barbiturates
hexylresorcinol [no description available]	2.07	1	0	resorcinols
ethidium Ethidium: A trypanocidal agent and possible antiviral agent that is widely used in experimental cell biology and biochemistry. Ethidium has several experimentally useful properties including binding to nucleic acids, noncompetitive inhibition of nicotinic acetylcholine receptors, and fluorescence among others. It is most commonly used as the bromide.. ethidium : The fluorescent compound widely used in experimental cell biology and biochemistry to reveal double-stranded DNA and RNA.	2.81	3	0	phenanthridines	fluorochrome; intercalator
hydrochlorothiazide Hydrochlorothiazide: A thiazide diuretic often considered the prototypical member of this class. It reduces the reabsorption of electrolytes from the renal tubules. This results in increased excretion of water and electrolytes, including sodium, potassium, chloride, and magnesium. It is used in the treatment of several disorders including edema, hypertension, diabetes insipidus, and hypoparathyroidism.. hydrochlorothiazide : A benzothiadiazine that is 3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide substituted by a chloro group at position 6 and a sulfonamide at 7. It is diuretic used for the treatment of hypertension and congestive heart failure.	2.15	1	0	benzothiadiazine; organochlorine compound; sulfonamide	antihypertensive agent; diuretic; environmental contaminant; xenobiotic
hydroxychloroquine Hydroxychloroquine: A chemotherapeutic agent that acts against erythrocytic forms of malarial parasites. Hydroxychloroquine appears to concentrate in food vacuoles of affected protozoa. It inhibits plasmodial heme polymerase. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p970). hydroxychloroquine : An aminoquinoline that is chloroquine in which one of the N-ethyl groups is hydroxylated at position 2. An antimalarial with properties similar to chloroquine that acts against erythrocytic forms of malarial parasites, it is mainly used as the sulfate salt for the treatment of lupus erythematosus, rheumatoid arthritis, and light-sensitive skin eruptions.	2.31	1	0	aminoquinoline; organochlorine compound; primary alcohol; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; antirheumatic drug; dermatologic drug
hydroxyurea [no description available]	1.96	1	0	one-carbon compound; ureas	antimetabolite; antimitotic; antineoplastic agent; DNA synthesis inhibitor; EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor; genotoxin; immunomodulator; radical scavenger; teratogenic agent
ibuprofen Midol: combination of cinnamedrine, phenacetin, aspirin & caffeine	3.81	3	0	monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; radical scavenger; xenobiotic
lidocaine Lidocaine: A local anesthetic and cardiac depressant used as an antiarrhythmia agent. Its actions are more intense and its effects more prolonged than those of PROCAINE but its duration of action is shorter than that of BUPIVACAINE or PRILOCAINE.. lidocaine : The monocarboxylic acid amide resulting from the formal condensation of N,N-diethylglycine with 2,6-dimethylaniline.	3.08	5	0	benzenes; monocarboxylic acid amide; tertiary amino compound	anti-arrhythmia drug; drug allergen; environmental contaminant; local anaesthetic; xenobiotic
mephentermine Mephentermine: A sympathomimetic agent with specificity for alpha-1 adrenergic receptors. It is used to maintain BLOOD PRESSURE in hypotensive states such as following SPINAL ANESTHESIA.	2.1	1	0	amphetamines
ifenprodil ifenprodil: NMDA receptor antagonist	2.45	2	0	piperidines
imipramine Imipramine: The prototypical tricyclic antidepressant. It has been used in major depression, dysthymia, bipolar depression, attention-deficit disorders, agoraphobia, and panic disorders. It has less sedative effect than some other members of this therapeutic group.. imipramine : A dibenzoazepine that is 5H-dibenzo[b,f]azepine substituted by a 3-(dimethylamino)propyl group at the nitrogen atom.	4.02	4	0	dibenzoazepine	adrenergic uptake inhibitor; antidepressant; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
amrinone Amrinone: A positive inotropic cardiotonic (CARDIOTONIC AGENTS) with vasodilator properties, phosphodiesterase 3 inhibitory activity, and the ability to stimulate calcium ion influx into the cardiac cell.. amrinone : A 3,4'-bipyridine substituted at positions 5 and 6 by an amino group and a keto function respectively. A pyridine phosphodiesterase 3 inhibitor, it is a drug that may improve the prognosis in patients with congestive heart failure.	1.96	1	0	bipyridines	EC 3.1.4.* (phosphoric diester hydrolase) inhibitor
indole-3-carbinol indole-3-carbinol: occurs in edible cruciferous vegetables. indole-3-methanol : An indolyl alcohol carrying a hydroxymethyl group at position 3. It is a constituent of the cruciferous vegetables and had anticancer activity.	2.02	1	0	indolyl alcohol	antineoplastic agent; plant metabolite
indomethacin Indomethacin: A non-steroidal anti-inflammatory agent (NSAID) that inhibits CYCLOOXYGENASE, which is necessary for the formation of PROSTAGLANDINS and other AUTACOIDS. It also inhibits the motility of POLYMORPHONUCLEAR LEUKOCYTES.. indometacin : A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by p-chlorobenzoyl, methyl, and methoxy groups, respectively. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis.	5.57	23	0	aromatic ether; indole-3-acetic acids; monochlorobenzenes; N-acylindole	analgesic; drug metabolite; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; gout suppressant; non-steroidal anti-inflammatory drug; xenobiotic metabolite; xenobiotic
avapro Irbesartan: A spiro compound, biphenyl and tetrazole derivative that acts as an angiotensin II type 1 receptor antagonist. It is used in the management of HYPERTENSION, and in the treatment of kidney disease.. irbesartan : A biphenylyltetrazole that is an angiotensin II receptor antagonist used mainly for the treatment of hypertension.	2.17	1	0	azaspiro compound; biphenylyltetrazole	angiotensin receptor antagonist; antihypertensive agent; environmental contaminant; xenobiotic
1-methyl-3-isobutylxanthine 1-Methyl-3-isobutylxanthine: A potent cyclic nucleotide phosphodiesterase inhibitor; due to this action, the compound increases cyclic AMP and cyclic GMP in tissue and thereby activates CYCLIC NUCLEOTIDE-REGULATED PROTEIN KINASES. 3-isobutyl-1-methylxanthine : An oxopurine that is xanthine which is substituted at positions 1 and 3 by methyl and isobutyl groups, respectively.	3.98	14	0	3-isobutyl-1-methylxanthine
isoniazid Hydra: A genus of freshwater polyps in the family Hydridae, order Hydroida, class HYDROZOA. They are of special interest because of their complex organization and because their adult organization corresponds roughly to the gastrula of higher animals.. hydrazide : Compounds derived from oxoacids RkE(=O)l(OH)m (l =/= 0) by replacing -OH by -NRNR2 (R groups are commonly H). (IUPAC).	7.69	2	0	carbohydrazide	antitubercular agent; drug allergen
2-propanol 2-Propanol: An isomer of 1-PROPANOL. It is a colorless liquid having disinfectant properties. It is used in the manufacture of acetone and its derivatives and as a solvent. Topically, it is used as an antiseptic.. propan-2-ol : A secondary alcohol that is propane in which one of the hydrogens attached to the central carbon is substituted by a hydroxy group.	2.05	1	0	secondary alcohol; secondary fatty alcohol	protic solvent
isoproterenol Isoproterenol: Isopropyl analog of EPINEPHRINE; beta-sympathomimetic that acts on the heart, bronchi, skeletal muscle, alimentary tract, etc. It is used mainly as bronchodilator and heart stimulant.. isoprenaline : A secondary amino compound that is noradrenaline in which one of the hydrogens attached to the nitrogen is replaced by an isopropyl group. A sympathomimetic acting almost exclusively on beta-adrenergic receptors, it is used (mainly as the hydrochloride salt) as a bronghodilator and heart stimulant for the management of a variety of cardiac disorders.	4.55	25	0	catechols; secondary alcohol; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; cardiotonic drug; sympathomimetic agent
isradipine Isradipine: A potent antagonist of CALCIUM CHANNELS that is highly selective for VASCULAR SMOOTH MUSCLE. It is effective in the treatment of chronic stable angina pectoris, hypertension, and congestive cardiac failure.	1.98	1	0	benzoxadiazole; dihydropyridine; isopropyl ester; methyl ester
juglone juglone: structure. juglone : A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogen at position 5 has been replaced by a hydroxy group. A plant-derived 1,4-naphthoquinone with confirmed antibacterial and antitumor activities.	2.1	1	0	hydroxy-1,4-naphthoquinone	geroprotector; herbicide; reactive oxygen species generator
ketamine Ketamine: A cyclohexanone derivative used for induction of anesthesia. Its mechanism of action is not well understood, but ketamine can block NMDA receptors (RECEPTORS, N-METHYL-D-ASPARTATE) and may interact with sigma receptors.. ketamine : A member of the class of cyclohexanones in which one of the hydrogens at position 2 is substituted by a 2-chlorophenyl group, while the other is substituted by a methylamino group.	3.16	5	0	cyclohexanones; monochlorobenzenes; secondary amino compound	analgesic; environmental contaminant; intravenous anaesthetic; neurotoxin; NMDA receptor antagonist; xenobiotic
ketanserin Ketanserin: A selective serotonin receptor antagonist with weak adrenergic receptor blocking properties. The drug is effective in lowering blood pressure in essential hypertension. It also inhibits platelet aggregation. It is well tolerated and is particularly effective in older patients.. ketanserin : A member of the class of quinazolines that is quinazoline-2,4(1H,3H)-dione which is substituted at position 3 by a 2-[4-(p-fluorobenzoyl)piperidin-1-yl]ethyl group.	2.37	2	0	aromatic ketone; organofluorine compound; piperidines; quinazolines	alpha-adrenergic antagonist; antihypertensive agent; cardiovascular drug; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; serotonergic antagonist
ketoconazole 1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine : A dioxolane that is 1,3-dioxolane which is substituted at positions 2, 2, and 4 by imidazol-1-ylmethyl, 2,4-dichlorophenyl, and [para-(4-acetylpiperazin-1-yl)phenoxy]methyl groups, respectively.	2.45	2	0	dichlorobenzene; dioxolane; ether; imidazoles; N-acylpiperazine; N-arylpiperazine
ketoprofen Ketoprofen: An IBUPROFEN-type anti-inflammatory analgesic and antipyretic. It is used in the treatment of rheumatoid arthritis and osteoarthritis.. ketoprofen : An oxo monocarboxylic acid that consists of propionic acid substituted by a 3-benzoylphenyl group at position 2.	3.54	2	0	benzophenones; oxo monocarboxylic acid	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-steroidal anti-inflammatory drug; xenobiotic
ketorolac Ketorolac: A pyrrolizine carboxylic acid derivative structurally related to INDOMETHACIN. It is an NSAID and is used principally for its analgesic activity. (From Martindale The Extra Pharmacopoeia, 31st ed). ketorolac : A racemate comprising equimolar amounts of (R)-(+)- and (S)-(-)-5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid. While only the (S)-(-) enantiomer is a COX1 and COX2 inhibitor, the (R)-(+) enantiomer exhibits potent analgesic activity. A non-steroidal anti-inflammatory drug, ketorolac is mainly used (generally as the tromethamine salt) for its potent analgesic properties in the short-term management of post-operative pain, and in eye drops to relieve the ocular itching associated with seasonal allergic conjunctivitis. It was withdrawn from the market in many countries in 1993 following association with haemorrhage and renal failure.. 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid : A member of the class of pyrrolizines that is 2,3-dihydro-1H-pyrrolizine which is substituted at positions 1 and 5 by carboxy and benzoyl groups, respectively.	2.1	1	0	amino acid; aromatic ketone; monocarboxylic acid; pyrrolizines; racemate	analgesic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; non-steroidal anti-inflammatory drug
ketotifen Ketotifen: A cycloheptathiophene blocker of histamine H1 receptors and release of inflammatory mediators. It has been proposed for the treatment of asthma, rhinitis, skin allergies, and anaphylaxis.. ketotifen : An organic heterotricyclic compound that is 4,9-dihydro-10H-benzo[4,5]cyclohepta[1,2-b]thiophen-10-one which is substituted at position 4 by a 1-methylpiperidin-4-ylidene group. A blocker of histamine H1 receptors with a stabilising action on mast cells, it is used (usually as its hydrogen fumarate salt) for the treatment of asthma, where it may take several weeks to exert its full effect.	3.1	1	0	cyclic ketone; olefinic compound; organic heterotricyclic compound; organosulfur heterocyclic compound; piperidines; tertiary amino compound	anti-asthmatic drug; H1-receptor antagonist
khellin Khellin: A vasodilator that also has bronchodilatory action. It has been employed in the treatment of angina pectoris, in the treatment of asthma, and in conjunction with ultraviolet light A, has been tried in the treatment of vitiligo. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1024). khellin : A furanochrome in which the basic tricyclic skeleton is substituted at positions 4 and 9 with methoxy groups and at position 7 with a methyl group. A major constituent of the plant Ammi visnaga it is a herbal folk medicine used for various illnesses, its main effect being as a vasodilator.	2.17	1	0	furanochromone; organic heterotricyclic compound; oxacycle	anti-asthmatic agent; bronchodilator agent; cardiovascular drug; vasodilator agent
kinetin Kinetin: A furanyl adenine found in PLANTS and FUNGI. It has plant growth regulation effects.. cytokinin : A phytohormone that promote cell division, or cytokinesis, in plant roots and shoots.. kinetin : A member of the class of 6-aminopurines that is adenine carrying a (furan-2-ylmethyl) substituent at the exocyclic amino group.	2.08	1	0	6-aminopurines; furans	cytokinin; geroprotector
kojic acid [no description available]	2.87	3	0	4-pyranones; enol; primary alcohol	Aspergillus metabolite; EC 1.10.3.1 (catechol oxidase) inhibitor; EC 1.10.3.2 (laccase) inhibitor; EC 1.13.11.24 (quercetin 2,3-dioxygenase) inhibitor; EC 1.14.18.1 (tyrosinase) inhibitor; EC 1.4.3.3 (D-amino-acid oxidase) inhibitor; NF-kappaB inhibitor; skin lightening agent
kynurenic acid Kynurenic Acid: A broad-spectrum excitatory amino acid antagonist used as a research tool.. kynurenic acid : A quinolinemonocarboxylic acid that is quinoline-2-carboxylic acid substituted by a hydroxy group at C-4.	2.44	2	0	monohydroxyquinoline; quinolinemonocarboxylic acid	G-protein-coupled receptor agonist; human metabolite; neuroprotective agent; nicotinic antagonist; NMDA receptor antagonist; Saccharomyces cerevisiae metabolite
3-phenyllactic acid 3-phenyllactic acid: alpha-hydroxy analog of phenylalanine; RN given refers to cpd without isomeric designation. 3-phenyllactic acid : A 2-hydroxy monocarboxylic acid that is lactic acid in which one of the methyl hydrogens is substituted by a phenyl group.	2.17	1	0	2-hydroxy monocarboxylic acid	human metabolite
2-amino-3-phosphonopropionic acid 2-amino-3-phosphonopropionic acid: metabotropic glutamate receptor antagonist; do not confuse AP-3 used as an abbreviation for this with enhancer-binding protein AP-3 (a trans-activator) or clathrin assembly protein AP-3. 2-amino-3-phosphonopropanoic acid : A non-proteinogenc alpha-amino acid that is alanine in which one of the hydrogens of the terminal methyl group has been replaced by a dihydroxy(oxido)-lambda(5)-phosphanyl group.	2	1	0	alanine derivative; non-proteinogenic alpha-amino acid; phosphonic acids	human metabolite; metabotropic glutamate receptor antagonist
labetalol Labetalol: A salicylamide derivative that is a non-cardioselective blocker of BETA-ADRENERGIC RECEPTORS and ALPHA-1 ADRENERGIC RECEPTORS.. labetalol : A diastereoisomeric mixture of approximately equal amounts of all four possible stereoisomers ((R,S)-labetolol, (S,R)-labetolol, (S,S)-labetalol and (R,R)-labetalol). It is an adrenergic antagonist used to treat high blood pressure.. 2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzamide : A member of the class of benzamides that is benzamide substituted by a hydroxy group at position 2 and by a 1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl group at position 5.	3.54	2	0	benzamides; benzenes; phenols; primary carboxamide; salicylamides; secondary alcohol; secondary amino compound
lamotrigine [no description available]	3.1	1	0	1,2,4-triazines; dichlorobenzene; primary arylamine	anticonvulsant; antidepressant; antimanic drug; calcium channel blocker; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; environmental contaminant; excitatory amino acid antagonist; geroprotector; non-narcotic analgesic; xenobiotic
lansoprazole Lansoprazole: A 2,2,2-trifluoroethoxypyridyl derivative of timoprazole that is used in the therapy of STOMACH ULCERS and ZOLLINGER-ELLISON SYNDROME. The drug inhibits H(+)-K(+)-EXCHANGING ATPASE which is found in GASTRIC PARIETAL CELLS. Lansoprazole is a racemic mixture of (R)- and (S)-isomers.	2.03	1	0	benzimidazoles; pyridines; sulfoxide	anti-ulcer drug; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor
lauric acid dodecanoic acid : A straight-chain, twelve-carbon medium-chain saturated fatty acid with strong bactericidal properties; the main fatty acid in coconut oil and palm kernel oil.	9.94	2	1	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; antibacterial agent; plant metabolite
tetramisole 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole : An imidazothiazole that is imidazo[2,1-b][1,3]thiazole in which the double bonds at the 2-3 and 5-6 positions have been reduced to single bonds and in which one of the hydrogens at position 6 is replaced by a phenyl group.. tetramisole : A racemate comprising equimolar amounts of levamisole and dexamisole.	2	1	0	imidazothiazole	environmental contaminant; xenobiotic
lidoflazine Lidoflazine: Coronary vasodilator with some antiarrhythmic action.	1.97	1	0	diarylmethane
lomefloxacin lomefloxacin: structure given in first source. lomefloxacin : A fluoroquinolone antibiotic, used (generally as the hydrochloride salt) to treat bacterial infections including bronchitis and urinary tract infections. It is also used to prevent urinary tract infections prior to surgery.	2.5	2	0	fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone	antimicrobial agent; antitubercular agent; photosensitizing agent
lorazepam Lorazepam: A benzodiazepine used as an anti-anxiety agent with few side effects. It also has hypnotic, anticonvulsant, and considerable sedative properties and has been proposed as a preanesthetic agent.	3.1	1	0	benzodiazepine
losartan Losartan: An antagonist of ANGIOTENSIN TYPE 1 RECEPTOR with antihypertensive activity due to the reduced pressor effect of ANGIOTENSIN II.. losartan : A biphenylyltetrazole where a 1,1'-biphenyl group is attached at the 5-position and has an additional trisubstituted imidazol-1-ylmethyl group at the 4'-position	3.8	3	0	biphenylyltetrazole; imidazoles	angiotensin receptor antagonist; anti-arrhythmia drug; antihypertensive agent; endothelin receptor antagonist
loxapine Loxapine: An antipsychotic agent used in SCHIZOPHRENIA.	3.54	2	0	dibenzooxazepine	antipsychotic agent; dopaminergic antagonist
2-(4-morpholinyl)-8-phenyl-4h-1-benzopyran-4-one 2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one: specific inhibitor of phosphatidylinositol 3-kinase; structure in first source	2.69	2	0	chromones; morpholines; organochlorine compound	autophagy inhibitor; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor; geroprotector
maprotiline Maprotiline: A bridged-ring tetracyclic antidepressant that is both mechanistically and functionally similar to the tricyclic antidepressants, including side effects associated with its use.	2.1	1	0	anthracenes
mefenamic acid Mefenamic Acid: A non-steroidal anti-inflammatory agent with analgesic, anti-inflammatory, and antipyretic properties. It is an inhibitor of cyclooxygenase.. mefenamic acid : An aminobenzoic acid that is anthranilic acid in which one of the hydrogens attached to the nitrogen is replaced by a 2,3-dimethylphenyl group. Although classed as a non-steroidal anti-inflammatory drug, its anti-inflammatory properties are considered to be minor. It is used to relieve mild to moderate pain, including headaches, dental pain, osteoarthritis and rheumatoid arthritis.	2.1	1	0	aminobenzoic acid; secondary amino compound	analgesic; antipyretic; antirheumatic drug; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-steroidal anti-inflammatory drug; xenobiotic
mefloquine hydrochloride [2,8-bis(trifluoromethyl)quinolin-4-yl]-(2-piperidyl)methanol : An organofluorine compound that consists of quinoline bearing trifluoromethyl substituents at positions 2 and 8 as well as a (2-piperidinyl)hydroxymethyl substituent at position 4.	2	1	0	organofluorine compound; piperidines; quinolines; secondary alcohol
memantine [no description available]	1.99	1	0	adamantanes; primary aliphatic amine	antidepressant; antiparkinson drug; dopaminergic agent; neuroprotective agent; NMDA receptor antagonist
vitamin k 3 Vitamin K 3: A synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo.	2.6	1	0	1,4-naphthoquinones; vitamin K	angiogenesis inhibitor; antineoplastic agent; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; human urinary metabolite; nutraceutical
mepenzolate mepenzolic acid: anticholinergic, antispasmodic agent; RN given refers to parent cpd; structure	1.97	1	0	diarylmethane
meperidine Meperidine: A narcotic analgesic that can be used for the relief of most types of moderate to severe pain, including postoperative pain and the pain of labor. Prolonged use may lead to dependence of the morphine type; withdrawal symptoms appear more rapidly than with morphine and are of shorter duration.. pethidine : A piperidinecarboxylate ester that is piperidine which is substituted by a methyl group at position 1 and by phenyl and ethoxycarbonyl groups at position 4. It is an analgesic which is used for the treatment of moderate to severe pain, including postoperative pain and labour pain.	3.54	2	0	ethyl ester; piperidinecarboxylate ester; tertiary amino compound	antispasmodic drug; kappa-opioid receptor agonist; mu-opioid receptor agonist; opioid analgesic
mesalamine Mesalamine: An anti-inflammatory agent, structurally related to the SALICYLATES, which is active in INFLAMMATORY BOWEL DISEASE. It is considered to be the active moiety of SULPHASALAZINE. (From Martindale, The Extra Pharmacopoeia, 30th ed). mesalamine : A monohydroxybenzoic acid that is salicylic acid substituted by an amino group at the 5-position.	4.01	4	0	amino acid; aromatic amine; monocarboxylic acid; monohydroxybenzoic acid; phenols	non-steroidal anti-inflammatory drug
mescaline Mescaline: Hallucinogenic alkaloid isolated from the flowering heads (peyote) of Lophophora (formerly Anhalonium) williamsii, a Mexican cactus used in Indian religious rites and as an experimental psychotomimetic. Among its cellular effects are agonist actions at some types of serotonin receptors. It has no accepted therapeutic uses although it is legal for religious use by members of the Native American Church.. mescaline : A phenethylamine alkaloid that is phenethylamine substituted at positions 3, 4 and 5 by methoxy groups.	2.38	2	0	methoxybenzenes; phenethylamine alkaloid; primary amino compound	hallucinogen
mesoridazine Mesoridazine: A phenothiazine antipsychotic with effects similar to CHLORPROMAZINE.. mesoridazine : A phenothiazine substituted at position 2 (para to the S atom) by a methylsulfinyl group, and on the nitrogen by a 2-(1-methylpiperidin-2-yl)ethyl group.	2.1	1	0	phenothiazines; sulfoxide; tertiary amino compound	dopaminergic antagonist; first generation antipsychotic
metformin Metformin: A biguanide hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. Metformin improves glycemic control by improving insulin sensitivity and decreasing intestinal absorption of glucose. (From Martindale, The Extra Pharmacopoeia, 30th ed, p289). metformin : A member of the class of guanidines that is biguanide the carrying two methyl substituents at position 1.	3.54	5	0	guanidines	environmental contaminant; geroprotector; hypoglycemic agent; xenobiotic
methenamine Methenamine: An anti-infective agent most commonly used in the treatment of urinary tract infections. Its anti-infective action derives from the slow release of formaldehyde by hydrolysis at acidic pH. (From Martindale, The Extra Pharmacopoeia, 30th ed, p173). hexamethylenetetramine : A polycyclic cage that is adamantane in which the carbon atoms at positions 1, 3, 5 and 7 are replaced by nitrogen atoms.	2.1	1	0	polyazaalkane; polycyclic cage; tetramine	antibacterial drug
methoxyphenamine methoxyphenamine: structure. methoxyphenamine : An amphetamine methylated on nitrogen and with the phenyl ring methoxylated at C-2. A beta-adrenergic receptor agonist, it is used as a bronchodilator.	2.1	1	0	amphetamines	beta-adrenergic agonist; bronchodilator agent
nocodazole [no description available]	1.96	1	0	aromatic ketone; benzimidazoles; carbamate ester; thiophenes	antimitotic; antineoplastic agent; microtubule-destabilising agent; tubulin modulator
methyl salicylate methyl salicylate: used in over-the-counter liniments, ointments, lotions for relief of musculoskeletal aches and pains; has hemolytic effect on human & sheep erythrocytes; RN given refers to parent cpd; structure in Merck Index, 9th ed, #5990. methyl salicylate : A benzoate ester that is the methyl ester of salicylic acid.	2.07	1	0	benzoate ester; methyl ester; salicylates	flavouring agent; insect attractant; metabolite
3-Hydroxy-alpha-methyl-DL-tyrosine [no description available]	2.1	1	0	benzenes; monocarboxylic acid
methyl methanesulfonate [no description available]	1.96	1	0	methanesulfonate ester	alkylating agent; apoptosis inducer; carcinogenic agent; genotoxin; mutagen
metoclopramide Metoclopramide: A dopamine D2 antagonist that is used as an antiemetic.. metoclopramide : A member of the class of benzamides resulting from the formal condensation of 4-amino-5-chloro-2-methoxybenzoic acid with the primary amino group of N,N-diethylethane-1,2-diamine.	2.1	1	0	benzamides; monochlorobenzenes; substituted aniline; tertiary amino compound	antiemetic; dopaminergic antagonist; environmental contaminant; gastrointestinal drug; xenobiotic
metoprolol Metoprolol: A selective adrenergic beta-1 blocking agent that is commonly used to treat ANGINA PECTORIS; HYPERTENSION; and CARDIAC ARRHYTHMIAS.. metoprolol : A propanolamine that is 1-(propan-2-ylamino)propan-2-ol substituted by a 4-(2-methoxyethyl)phenoxy group at position 1.	7.52	2	0	aromatic ether; propanolamine; secondary alcohol; secondary amino compound	antihypertensive agent; beta-adrenergic antagonist; environmental contaminant; geroprotector; xenobiotic
metronidazole Metronidazole: A nitroimidazole used to treat AMEBIASIS; VAGINITIS; TRICHOMONAS INFECTIONS; GIARDIASIS; ANAEROBIC BACTERIA; and TREPONEMAL INFECTIONS.. metronidazole : A member of the class of imidazoles substituted at C-1, -2 and -5 with 2-hydroxyethyl, nitro and methyl groups respectively. It has activity against anaerobic bacteria and protozoa, and has a radiosensitising effect on hypoxic tumour cells. It may be given by mouth in tablets, or as the benzoate in an oral suspension. The hydrochloride salt can be used in intravenous infusions. Metronidazole is a prodrug and is selective for anaerobic bacteria due to their ability to intracellularly reduce the nitro group of metronidazole to give nitroso-containing intermediates. These can covalently bind to DNA, disrupting its helical structure, inducing DNA strand breaks and inhibiting bacterial nucleic acid synthesis, ultimately resulting in bacterial cell death.	4.11	2	1	C-nitro compound; imidazoles; primary alcohol	antiamoebic agent; antibacterial drug; antimicrobial agent; antiparasitic agent; antitrichomonal drug; environmental contaminant; prodrug; radiosensitizing agent; xenobiotic
metyrapone Metyrapone: An inhibitor of the enzyme STEROID 11-BETA-MONOOXYGENASE. It is used as a test of the feedback hypothalamic-pituitary mechanism in the diagnosis of CUSHING SYNDROME.. metyrapone : An aromatic ketone that is 3,3-dimethylbutan-2-one in which the methyl groups at positions 1 and 4 are replaced by pyridin-3-yl groups. A steroid 11beta-monooxygenase (EC 1.14.15.4) inhibitor, it is used in the diagnosis of adrenal insufficiency.	1.95	1	0	aromatic ketone	antimetabolite; diagnostic agent; EC 1.14.15.4 (steroid 11beta-monooxygenase) inhibitor
mexiletine Mexiletine: Antiarrhythmic agent pharmacologically similar to LIDOCAINE. It may have some anticonvulsant properties.. mexiletine : An aromatic ether which is 2,6-dimethylphenyl ether of 2-aminopropan-1-ol.	3.54	2	0	aromatic ether; primary amino compound	anti-arrhythmia drug
miconazole Miconazole: An imidazole antifungal agent that is used topically and by intravenous infusion.. 1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole : A member of the class of imidazoles that is 1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanol in which the hydroxyl hydrogen is replaced by a 2,4-dichlorobenzyl group.. miconazole : A racemate composed of equimolar amounts of (R)- and (S)-miconazole. Used (as its nitrate salt) to treat skin infections such as athlete's foot, jock itch, ringworm and other fungal skin infections. It inhibits the synthesis of ergosterol, a critical component of fungal cell membranes.	2.05	1	0	dichlorobenzene; ether; imidazoles
minoxidil Minoxidil: A potent direct-acting peripheral vasodilator (VASODILATOR AGENTS) that reduces peripheral resistance and produces a fall in BLOOD PRESSURE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p371). minoxidil : A pyrimidine N-oxide that is pyrimidine-2,4-diamine 3-oxide substituted by a piperidin-1-yl group at position 6.	1.98	1	0	dialkylarylamine; tertiary amino compound
mirtazapine Mirtazapine: A piperazinoazepine tetracyclic compound that enhances the release of NOREPINEPHRINE and SEROTONIN through blockage of presynaptic ALPHA-2 ADRENERGIC RECEPTORS. It also blocks both 5-HT2 and 5-HT3 serotonin receptors and is a potent HISTAMINE H1 RECEPTOR antagonist. It is used for the treatment of depression, and may also be useful for the treatment of anxiety disorders.	2.1	1	0	benzazepine; tetracyclic antidepressant	alpha-adrenergic antagonist; anxiolytic drug; H1-receptor antagonist; histamine antagonist; oneirogen; serotonergic antagonist
mitoxantrone Mitoxantrone: An anthracenedione-derived antineoplastic agent.. mitoxantrone : A dihydroxyanthraquinone that is 1,4-dihydroxy-9,10-anthraquinone which is substituted by 6-hydroxy-1,4-diazahexyl groups at positions 5 and 8.	3.1	1	0	dihydroxyanthraquinone	analgesic; antineoplastic agent
molsidomine Molsidomine: A morpholinyl sydnone imine ethyl ester, having a nitrogen in place of the keto oxygen. It acts as NITRIC OXIDE DONORS and is a vasodilator that has been used in ANGINA PECTORIS.. molsidomine : A member of the class of oxadiazoles that is 1,2,3-oxadiazole substituted by morpholin-4-yl and (ethoxycarbonyl)azanidyl groups at positions 3 and 5, respectively. It is used as a vasodilator drug for the treatment of myocardial ischemic syndrome and congestive heart failure.	2.42	2	0	ethyl ester; morpholines; oxadiazole; zwitterion	antioxidant; apoptosis inhibitor; cardioprotective agent; nitric oxide donor; vasodilator agent
muscimol Muscimol: A neurotoxic isoxazole isolated from species of AMANITA. It is obtained by decarboxylation of IBOTENIC ACID. Muscimol is a potent agonist of GABA-A RECEPTORS and is used mainly as an experimental tool in animal and tissue studies.. muscimol : A member of the class of isoxazoles that is 1,2-oxazol-3(2H)-one substituted by an aminomethyl group at position 5. It has been isolated from mushrooms of the genus Amanita.	1.98	1	0	alkaloid; isoxazoles; primary amino compound	fungal metabolite; GABA agonist; oneirogen; psychotropic drug
w 12 W 12: calmodulin antagonist; W13 analog with Cl deleted from benzene ring	1.96	1	0	naphthalenes; sulfonic acid derivative
n-(4-aminobutyl)-5-chloro-2-naphthalenesulfonamide N-(4-aminobutyl)-5-chloro-2-naphthalenesulfonamide: calmodulin antagonist; structure given in first source. N-(4-aminobutyl)-5-chloronaphthalene-2-sulfonamide : A sulfonamide that is 5-chloronaphthalene-2-sulfonamide in which one of the hydrogens of the nitrogen atom is substituted by a 4-aminobutyl group.	1.96	1	0	naphthalenes; organochlorine compound; primary amino compound; sulfonamide
n-(6-aminohexyl)-1-naphthalenesulfonamide N-(6-aminohexyl)-1-naphthalenesulfonamide: calmodulin antagonist; RN given refers to parent cpd	3.07	5	0	naphthalenes; sulfonic acid derivative
ethylmaleimide Ethylmaleimide: A sulfhydryl reagent that is widely used in experimental biochemical studies.	3.08	5	0	maleimides	anticoronaviral agent; EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor; EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor; EC 2.7.1.1 (hexokinase) inhibitor
fenamic acid fenamic acid: has chloride and potassium channel-blocking activity; RN given refers to parent cpd. fenamic acid : An aminobenzoic acid that is the N-phenyl derivative of anthranilic acid. It acts as a parent skeleton for the synthesis of several non-steroidal anti-inflammatory drugs.	2.02	1	0	aminobenzoic acid; secondary amino compound	membrane transport modulator
nalidixic acid [no description available]	2.47	2	0	1,8-naphthyridine derivative; monocarboxylic acid; quinolone antibiotic	antibacterial drug; antimicrobial agent; DNA synthesis inhibitor
nefazodone nefazodone: may be useful as an opiate adjunct	2.1	1	0	aromatic ether; monochlorobenzenes; N-alkylpiperazine; N-arylpiperazine; triazoles	alpha-adrenergic antagonist; analgesic; antidepressant; serotonergic antagonist; serotonin uptake inhibitor
nicardipine Nicardipine: A potent calcium channel blockader with marked vasodilator action. It has antihypertensive properties and is effective in the treatment of angina and coronary spasms without showing cardiodepressant effects. It has also been used in the treatment of asthma and enhances the action of specific antineoplastic agents.. nicardipine : A racemate comprising equimolar amounts of (R)- and (S)-nicardipine. It is a calcium channel blocker which is used to treat hypertension.. 2-[benzyl(methyl)amino]ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate : A dihydropyridine that is 1,4-dihydropyridine substituted by a methyl, {2-[benzyl(methyl)amino]ethoxy}carbonyl, 3-nitrophenyl, methoxycarbonyl and methyl groups at positions 2, 3, 4, 5 and 6, respectively.	3.48	8	0	benzenes; C-nitro compound; diester; dihydropyridine; methyl ester; tertiary amino compound
nifedipine Nifedipine: A potent vasodilator agent with calcium antagonistic action. It is a useful anti-anginal agent that also lowers blood pressure.	5.16	47	0	C-nitro compound; dihydropyridine; methyl ester	calcium channel blocker; human metabolite; tocolytic agent; vasodilator agent
niflumic acid Niflumic Acid: An analgesic and anti-inflammatory agent used in the treatment of rheumatoid arthritis.	2.7	3	0	aromatic carboxylic acid; pyridines
nimodipine Nimodipine: A calcium channel blockader with preferential cerebrovascular activity. It has marked cerebrovascular dilating effects and lowers blood pressure.. nimodipine : A dihydropyridine that is 1,4-dihydropyridine which is substituted by methyl groups at positions 2 and 6, a (2-methoxyethoxy)carbonyl group at position 3, a m-nitrophenyl group at position 4, and an isopropoxycarbonyl group at position 5. An L-type calcium channel blocker, it acts particularly on cerebral circulation, and is used both orally and intravenously for the prevention and treatment of subarachnoid hemorrhage from ruptured intracranial aneurysm.	4.64	6	1	2-methoxyethyl ester; C-nitro compound; dicarboxylic acids and O-substituted derivatives; diester; dihydropyridine; isopropyl ester	antihypertensive agent; calcium channel blocker; cardiovascular drug; vasodilator agent
nitrendipine Nitrendipine: A calcium channel blocker with marked vasodilator action. It is an effective antihypertensive agent and differs from other calcium channel blockers in that it does not reduce glomerular filtration rate and is mildly natriuretic, rather than sodium retentive.. nitrendipine : A dihydropyridine that is 1,4-dihydropyridine substituted by methyl groups at positions 2 and 6, a 3-nitrophenyl group at position 4, a ethoxycarbonyl group at position 3 and a methoxycarbonyl group at position 5. It is a calcium-channel blocker used in the treatment of hypertension.	2.65	3	0	C-nitro compound; dicarboxylic acids and O-substituted derivatives; diester; dihydropyridine; ethyl ester; methyl ester	antihypertensive agent; calcium channel blocker; geroprotector; vasodilator agent
nitroglycerin Nitroglycerin: A volatile vasodilator which relieves ANGINA PECTORIS by stimulating GUANYLATE CYCLASE and lowering cytosolic calcium. It is also sometimes used for TOCOLYSIS and explosives.. nitroglycerol : A nitrate ester that is glycerol in which nitro group(s) replace the hydrogen(s) attached to one or more of the hydroxy groups.. nitroglycerin : A nitroglycerol that is glycerol in which the hydrogen atoms of all three hydroxy groups are replaced by nitro groups. It acts as a prodrug, releasing nitric oxide to open blood vessels and so alleviate heart pain.	1.94	1	0	nitroglycerol	explosive; muscle relaxant; nitric oxide donor; prodrug; tocolytic agent; vasodilator agent; xenobiotic
masoprocol nordihydroguaretic acid: antioxidant compound found in the creosote bush (Larrea tridentata)	1.99	1	0	catechols; lignan; tetrol	antioxidant; ferroptosis inhibitor; geroprotector; plant metabolite
norfloxacin Norfloxacin: A synthetic fluoroquinolone (FLUOROQUINOLONES) with broad-spectrum antibacterial activity against most gram-negative and gram-positive bacteria. Norfloxacin inhibits bacterial DNA GYRASE.. norfloxacin : A quinolinemonocarboxylic acid with broad-spectrum antibacterial activity against most gram-negative and gram-positive bacteria. Norfloxacin is bactericidal and its mode of action depends on blocking of bacterial DNA replication by binding itself to an enzyme called DNA gyrase.	3.03	4	0	fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone	antibacterial drug; DNA synthesis inhibitor; environmental contaminant; xenobiotic
nortriptyline Nortriptyline: A metabolite of AMITRIPTYLINE that is also used as an antidepressive agent. Nortriptyline is used in major depression, dysthymia, and atypical depressions.. nortriptyline : An organic tricyclic compound that is 10,11-dihydro-5H-dibenzo[a,d][7]annulene substituted by a 3-(methylamino)propylidene group at position 5. It is an active metabolite of amitriptyline.	3.54	2	0	organic tricyclic compound; secondary amine	adrenergic uptake inhibitor; analgesic; antidepressant; antineoplastic agent; apoptosis inducer; drug metabolite
n-(2-cyclohexyloxy-4-nitrophenyl)methanesulfonamide N-(2-cyclohexyloxy-4-nitrophenyl)methanesulfonamide: structure given in first source. NS-398 : A C-nitro compound that is N-methylsulfonyl-4-nitroaniline bearing an additional cyclohexyloxy substituent at position 2.	2.7	3	0	aromatic ether; C-nitro compound; sulfonamide	antineoplastic agent; cyclooxygenase 2 inhibitor
octopamine Octopamine: An alpha-adrenergic sympathomimetic amine, biosynthesized from tyramine in the CNS and platelets and also in invertebrate nervous systems. It is used to treat hypotension and as a cardiotonic. The natural D(-) form is more potent than the L(+) form in producing cardiovascular adrenergic responses. It is also a neurotransmitter in some invertebrates.. octopamine : A member of the class of phenylethanolamines that is phenol which is substituted at the para- position by a 2-amino-1-hydroxyethyl group. A biogenic phenylethanolamine which has been found to act as a neurotransmitter, neurohormone or neuromodulator in invertebrates.	2.17	1	0	phenylethanolamines; tyramines	neurotransmitter
ofloxacin Ofloxacin: A synthetic fluoroquinolone antibacterial agent that inhibits the supercoiling activity of bacterial DNA GYRASE, halting DNA REPLICATION.. 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid : An oxazinoquinoline that is 2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinolin-7-one substituted by methyl, carboxy, fluoro, and 4-methylpiperazin-1-yl groups at positions 3, 6, 9, and 10, respectively.. ofloxacin : A racemate comprising equimolar amounts of levofloxacin and dextrofloxacin. It is a synthetic fluoroquinolone antibacterial agent which inhibits the supercoiling activity of bacterial DNA gyrase, halting DNA replication.	2.5	2	0	3-oxo monocarboxylic acid; N-arylpiperazine; N-methylpiperazine; organofluorine compound; oxazinoquinoline
oxonic acid Oxonic Acid: Antagonist of urate oxidase.	2.41	1	0	1,3,5-triazines; monocarboxylic acid
oxazepam Oxazepam: A benzodiazepine used in the treatment of anxiety, alcohol withdrawal, and insomnia.. oxazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a hydroxy group at position 3 and phenyl group at position 5.	3.1	1	0	1,4-benzodiazepinone; organochlorine compound	anxiolytic drug; environmental contaminant; xenobiotic
oxidopamine Oxidopamine: A neurotransmitter analogue that depletes noradrenergic stores in nerve endings and induces a reduction of dopamine levels in the brain. Its mechanism of action is related to the production of cytolytic free-radicals.. oxidopamine : A benzenetriol that is phenethylamine in which the hydrogens at positions 2, 4, and 5 on the phenyl ring are replaced by hydroxy groups. It occurs naturally in human urine, but is also produced as a metabolite of the drug DOPA (used for the treatment of Parkinson's disease).	3.44	7	0	benzenetriol; catecholamine; primary amino compound	drug metabolite; human metabolite; neurotoxin
oxotremorine Oxotremorine: A non-hydrolyzed muscarinic agonist used as a research tool.	2.42	2	0	N-alkylpyrrolidine
oxprenolol Oxprenolol: A beta-adrenergic antagonist used in the treatment of hypertension, angina pectoris, arrhythmias, and anxiety.	2.1	1	0	aromatic ether
oxybenzone oxybenzone : A hydroxybenzophenone that is benzophenone which is substituted at the 2- and 4-positions of one of the benzene rings by hydroxy and methoxy groups respectively.	2.11	1	0	hydroxybenzophenone; monomethoxybenzene	dermatologic drug; environmental contaminant; protective agent; ultraviolet filter; xenobiotic
oxybutynin oxybutynin: RN given refers to parent cpd. oxybutynin : A racemate comprising equimolar amounts of (R)-oxybutynin and esoxybutynin. An antispasmodic used for the treatment of overactive bladder.	2.21	1	0	acetylenic compound; carboxylic ester; racemate; tertiary alcohol; tertiary amino compound	antispasmodic drug; calcium channel blocker; local anaesthetic; muscarinic antagonist; muscle relaxant; parasympatholytic
oxyphenbutazone Oxyphenbutazone: A non-steroidal anti-inflammatory drug. Oxyphenbutazone eyedrops have been used abroad in the management of postoperative ocular inflammation, superficial eye injuries, and episcleritis. (From AMA, Drug Evaluations Annual, 1994, p2000) It had been used by mouth in rheumatic disorders such as ankylosing spondylitis, osteoarthritis, and rheumatoid arthritis but such use is no longer considered justified owing to the risk of severe hematological adverse effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p27). oxyphenbutazone : A metabolite of phenylbutazone obtained by hydroxylation at position 4 of one of the phenyl rings. Commonly used (as its hydrate) to treat pain, swelling and stiffness associated with arthritis and gout, it was withdrawn from the market 1984 following association with blood dyscrasis and Stevens-Johnson syndrome.	3.1	1	0	phenols; pyrazolidines	antimicrobial agent; antineoplastic agent; antipyretic; drug metabolite; gout suppressant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic metabolite
aminosalicylic acid Aminosalicylic Acid: An antitubercular agent often administered in association with ISONIAZID. The sodium salt of the drug is better tolerated than the free acid.. 4-aminosalicylic acid : An aminobenzoic acid that is salicylic acid substituted by an amino group at position 4.	3.54	2	0	aminobenzoic acid; phenols	antitubercular agent
quinone benzoquinone : The simplest members of the class of benzoquinones, consisting of cyclohexadiene which is substituted by two oxo groups.. 1,4-benzoquinone : The simplest member of the class of 1,4-benzoquinones, obtained by the formal oxidation of hydroquinone to the corresponding diketone. It is a metabolite of benzene.. quinone : Compounds having a fully conjugated cyclic dione structure, such as that of benzoquinones, derived from aromatic compounds by conversion of an even number of -CH= groups into -C(=O)- groups with any necessary rearrangement of double bonds (polycyclic and heterocyclic analogues are included).	3.63	9	0	1,4-benzoquinones	cofactor; human xenobiotic metabolite; mouse metabolite
pantoprazole Pantoprazole: 2-pyridinylmethylsulfinylbenzimidazole proton pump inhibitor that is used in the treatment of GASTROESOPHAGEAL REFLUX and PEPTIC ULCER.. pantoprazole : A member of the class of benzimidazoles that is 1H-benzimidazole substituted by a difluoromethoxy group at position 5 and a [(3,4-dimethoxypyridin-2-yl)methyl]sulfinyl group at position 2.	2.15	1	0	aromatic ether; benzimidazoles; organofluorine compound; pyridines; sulfoxide	anti-ulcer drug; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; environmental contaminant; xenobiotic
papaverine Papaverine: An alkaloid found in opium but not closely related to the other opium alkaloids in its structure or pharmacological actions. It is a direct-acting smooth muscle relaxant used in the treatment of impotence and as a vasodilator, especially for cerebral vasodilation. The mechanism of its pharmacological actions is not clear, but it apparently can inhibit phosphodiesterases and it may have direct actions on calcium channels.. papaverine : A benzylisoquinoline alkaloid that is isoquinoline substituted by methoxy groups at positions 6 and 7 and a 3,4-dimethoxybenzyl group at position 1. It has been isolated from Papaver somniferum.	1.96	1	0	benzylisoquinoline alkaloid; dimethoxybenzene; isoquinolines	antispasmodic drug; vasodilator agent
pd 98059 2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one: inhibits MAP kinase kinase (MEK) activity, p42 MAPK and p44 MAPK; structure in first source. 2-(2-amino-3-methoxyphenyl)chromen-4-one : A member of the class of monomethoxyflavones that is 3'-methoxyflavone bearing an additional amino substituent at position 2'.	3.27	6	0	aromatic amine; monomethoxyflavone	EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector
pentamidine Pentamidine: Antiprotozoal agent effective in trypanosomiasis, leishmaniasis, and some fungal infections; used in treatment of PNEUMOCYSTIS pneumonia in HIV-infected patients. It may cause diabetes mellitus, central nervous system damage, and other toxic effects.. pentamidine : A diether consisting of pentane-1,5-diol in which both hydroxyl hydrogens have been replaced by 4-amidinophenyl groups. A trypanocidal drug that is used for treatment of cutaneous leishmaniasis and Chagas disease.	2.13	1	0	aromatic ether; carboxamidine; diether	anti-inflammatory agent; antifungal agent; calmodulin antagonist; chemokine receptor 5 antagonist; EC 2.3.1.48 (histone acetyltransferase) inhibitor; NMDA receptor antagonist; S100 calcium-binding protein B inhibitor; trypanocidal drug; xenobiotic
pentobarbital Pentobarbital: A short-acting barbiturate that is effective as a sedative and hypnotic (but not as an anti-anxiety) agent and is usually given orally. It is prescribed more frequently for sleep induction than for sedation but, like similar agents, may lose its effectiveness by the second week of continued administration. (From AMA Drug Evaluations Annual, 1994, p236). pentobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and sec-pentyl groups.	2.42	2	0	barbiturates	GABAA receptor agonist
pentoxifylline [no description available]	1.98	1	0	oxopurine
periciazine periciazine: was heading 1963-94 (Prov 1963-72); use PHENOTHIAZINES to search PROPERICIAZINE 1966-94. periciazine : A member of the class of phenothiazines that is 10H-phenothiazine substituted by a 3-(4-hydroxypiperidin-1-yl)propyl group at the nitrogen atom and a carbonitrile group at position 2. Periciazine is a first generation antipsychotic.	2.1	1	0	hydroxypiperidine; nitrile; phenothiazines	adrenergic antagonist; first generation antipsychotic; sedative
pheniramine Pheniramine: One of the HISTAMINE H1 ANTAGONISTS with little sedative action. It is used in treatment of hay fever, rhinitis, allergic dermatoses, and pruritus.	3.1	1	0	pyridines; tertiary amino compound
phenobarbital Phenobarbital: A barbituric acid derivative that acts as a nonselective central nervous system depressant. It potentiates GAMMA-AMINOBUTYRIC ACID action on GABA-A RECEPTORS, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations.. phenobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and phenyl groups.	4.45	7	0	barbiturates	anticonvulsant; drug allergen; excitatory amino acid antagonist; sedative
phenolphthalein Phenolphthalein: An acid-base indicator which is colorless in acid solution, but turns pink to red as the solution becomes alkaline. It is used medicinally as a cathartic.	3.5	2	0	phenols
phenolsulfonphthalein Phenolsulfonphthalein: Red dye, pH indicator, and diagnostic aid for determination of renal function. It is used also for studies of the gastrointestinal and other systems.. phenol red : 3H-2,1-Benzoxathiole 1,1-dioxide in which both of the hydrogens at position 3 have been substituted by 4-hydroxyphenyl groups. A pH indicator changing colour from yellow below pH 6.8 to bright pink above pH 8.2, it is commonly used as an indicator in cell cultures and in home swimming pool test kits. It is also used in the (now infrequently performed) phenolsulfonphthalein (PSP) test for estimation of overall blood flow through the kidney.	3.5	2	0	2,1-benzoxathiole; arenesulfonate ester; phenols; sultone	acid-base indicator; diagnostic agent; two-colour indicator
phenoxybenzamine Phenoxybenzamine: An alpha-adrenergic antagonist with long duration of action. It has been used to treat hypertension and as a peripheral vasodilator.	1.99	1	0	aromatic amine
phenylbutazone Phenylbutazone: A butyl-diphenyl-pyrazolidinedione that has anti-inflammatory, antipyretic, and analgesic activities. It has been used in ANKYLOSING SPONDYLITIS; RHEUMATOID ARTHRITIS; and REACTIVE ARTHRITIS.. phenylbutazone : A member of the class of pyrazolidines that is 1,2-diphenylpyrazolidine-3,5-dione carrying a butyl group at the 4-position.	3.1	1	0	pyrazolidines	antirheumatic drug; EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor; metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; peripheral nervous system drug
phloretin [no description available]	2.11	1	0	dihydrochalcones	antineoplastic agent; plant metabolite
pindolol Pindolol: A moderately lipophilic beta blocker (ADRENERGIC BETA-ANTAGONISTS). It is non-cardioselective and has intrinsic sympathomimetic actions, but little membrane-stabilizing activity. (From Martindale, The Extra Pharmocopoeia, 30th ed, p638). pindolol : A member of the class of indols which is the 2-hydroxy-3-(isopropylamino)propyl ether derivative of 1H-indol-4-ol.	2.1	1	0	indoles; secondary amine	antiglaucoma drug; antihypertensive agent; beta-adrenergic antagonist; serotonergic antagonist; vasodilator agent
pirenzepine Pirenzepine: An antimuscarinic agent that inhibits gastric secretion at lower doses than are required to affect gastrointestinal motility, salivary, central nervous system, cardiovascular, ocular, and urinary function. It promotes the healing of duodenal ulcers and due to its cytoprotective action is beneficial in the prevention of duodenal ulcer recurrence. It also potentiates the effect of other antiulcer agents such as CIMETIDINE and RANITIDINE. It is generally well tolerated by patients.	2.39	2	0	pyridobenzodiazepine	anti-ulcer drug; antispasmodic drug; muscarinic antagonist
potassium chloride Potassium Chloride: A white crystal or crystalline powder used in BUFFERS; FERTILIZERS; and EXPLOSIVES. It can be used to replenish ELECTROLYTES and restore WATER-ELECTROLYTE BALANCE in treating HYPOKALEMIA.. potassium chloride : A metal chloride salt with a K(+) counterion.	4.28	19	0	inorganic chloride; inorganic potassium salt; potassium salt	fertilizer
4-aminobenzoic acid para-Aminobenzoates: Benzoic acids, salts, or esters that contain an amino group attached to carbon number 4 of the benzene ring structure.. 4-aminobenzoate : An aromatic amino-acid anion that is the conjugate base of 4-aminobenzoic acid.	2.05	1	0	aminobenzoate; aromatic amino-acid anion	Escherichia coli metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
pyridoxal phosphate-6-azophenyl-2',4'-disulfonic acid pyridoxal phosphate-6-azophenyl-2',4'-disulfonic acid: a novel antagonist that selectively blocks P2 purinoceptor receptors; a useful tool to study co-transmission in tissues when ATP and coexisting neurotransmitters act in concert. 5'-phosphopyridoxal-6-azobenzene-2,4-disulfonic acid : An arenesulfonic acid that is pyridoxal 5'-phosphate carrying an additional 2,4-disulfophenylazo substituent at position 6.	2.02	1	0	arenesulfonic acid; azobenzenes; methylpyridines; monohydroxypyridine; organic phosphate; pyridinecarbaldehyde	purinergic receptor P2X antagonist
prazosin Prazosin: A selective adrenergic alpha-1 antagonist used in the treatment of HEART FAILURE; HYPERTENSION; PHEOCHROMOCYTOMA; RAYNAUD DISEASE; PROSTATIC HYPERTROPHY; and URINARY RETENTION.. prazosin : A member of the class of piperazines that is piperazine substituted by a furan-2-ylcarbonyl group and a 4-amino-6,7-dimethoxyquinazolin-2-yl group at positions 1 and 4 respectively.	2.38	2	0	aromatic ether; furans; monocarboxylic acid amide; piperazines; quinazolines	alpha-adrenergic antagonist; antihypertensive agent; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
primaquine Primaquine: An aminoquinoline that is given by mouth to produce a radical cure and prevent relapse of vivax and ovale malarias following treatment with a blood schizontocide. It has also been used to prevent transmission of falciparum malaria by those returning to areas where there is a potential for re-introduction of malaria. Adverse effects include anemias and GI disturbances. (From Martindale, The Extra Pharmacopeia, 30th ed, p404). primaquine : An N-substituted diamine that is pentane-1,4-diamine substituted by a 6-methoxyquinolin-8-yl group at the N(4) position. It is a drug used in the treatment of malaria and Pneumocystis pneumonia.	2.39	2	0	aminoquinoline; aromatic ether; N-substituted diamine	antimalarial
probenecid Probenecid: The prototypical uricosuric agent. It inhibits the renal excretion of organic anions and reduces tubular reabsorption of urate. Probenecid has also been used to treat patients with renal impairment, and, because it reduces the renal tubular excretion of other drugs, has been used as an adjunct to antibacterial therapy.. probenecid : A sulfonamide in which the nitrogen of 4-sulfamoylbenzoic acid is substituted with two propyl groups.	3.54	2	0	benzoic acids; sulfonamide	uricosuric drug
probucol Probucol: A drug used to lower LDL and HDL cholesterol yet has little effect on serum-triglyceride or VLDL cholesterol. (From Martindale, The Extra Pharmacopoeia, 30th ed, p993).. probucol : A dithioketal that is propane-2,2-dithiol in which the hydrogens attached to both sulfur atoms are replaced by 3,5-di-tert-butyl-4-hydroxyphenyl groups. An anticholesteremic drug with antioxidant and anti-inflammatory properties, it is used to treat high levels of cholesterol in blood.	2	1	0	dithioketal; polyphenol	anti-inflammatory drug; anticholesteremic drug; antilipemic drug; antioxidant; cardiovascular drug
procainamide Procainamide: A class Ia antiarrhythmic drug that is structurally-related to PROCAINE.. procainamide : A benzamide that is 4-aminobenzamide substituted on the amide N by a 2-(diethylamino)ethyl group. It is a pharmaceutical antiarrhythmic agent used for the medical treatment of cardiac arrhythmias.	2.1	1	0	benzamides	anti-arrhythmia drug; platelet aggregation inhibitor; sodium channel blocker
procaine Procaine: A local anesthetic of the ester type that has a slow onset and a short duration of action. It is mainly used for infiltration anesthesia, peripheral nerve block, and spinal block. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1016).. procaine : A benzoate ester, formally the result of esterification of 4-aminobenzoic acid with 2-diethylaminoethanol but formed experimentally by reaction of ethyl 4-aminobenzoate with 2-diethylaminoethanol.	3.22	6	0	benzoate ester; substituted aniline; tertiary amino compound	central nervous system depressant; drug allergen; local anaesthetic; peripheral nervous system drug
promazine Promazine: A phenothiazine with actions similar to CHLORPROMAZINE but with less antipsychotic activity. It is primarily used in short-term treatment of disturbed behavior and as an antiemetic.. promazine : A phenothiazine deriative in which the phenothiazine tricycle has a 3-(dimethylaminopropyl) group at the N-10 position.	2.5	2	0	phenothiazines; tertiary amine	antiemetic; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; H1-receptor antagonist; muscarinic antagonist; phenothiazine antipsychotic drug; serotonergic antagonist
promethazine Promethazine: A phenothiazine derivative with histamine H1-blocking, antimuscarinic, and sedative properties. It is used as an antiallergic, in pruritus, for motion sickness and sedation, and also in animals.. promethazine : A tertiary amine that is a substituted phenothiazine in which the ring nitrogen at position 10 is attached to C-3 of an N,N-dimethylpropan-2-amine moiety.	3.98	4	0	phenothiazines; tertiary amine	anti-allergic agent; anticoronaviral agent; antiemetic; antipruritic drug; H1-receptor antagonist; local anaesthetic; sedative
propafenone Propafenone: An antiarrhythmia agent that is particularly effective in ventricular arrhythmias. It also has weak beta-blocking activity.. propafenone : An aromatic ketone that is 3-(propylamino)propane-1,2-diol in which the hydrogen of the primary hydroxy group is replaced by a 2-(3-phenylpropanoyl)phenyl group. It is a class 1C antiarrhythmic drug with local anesthetic effects, and is used as the hydrochloride salt in the management of supraventricular and ventricular arrhythmias.	2.1	1	0	aromatic ketone; secondary alcohol; secondary amino compound	anti-arrhythmia drug
propidium Propidium: Quaternary ammonium analog of ethidium; an intercalating dye with a specific affinity to certain forms of DNA and, used as diiodide, to separate them in density gradients; also forms fluorescent complexes with cholinesterase which it inhibits.	2.03	1	0	phenanthridines; quaternary ammonium ion	fluorochrome; intercalator
propofol Propofol: An intravenous anesthetic agent which has the advantage of a very rapid onset after infusion or bolus injection plus a very short recovery period of a couple of minutes. (From Smith and Reynard, Textbook of Pharmacology, 1992, 1st ed, p206). Propofol has been used as ANTICONVULSANTS and ANTIEMETICS.. propofol : A phenol resulting from the formal substitution of the hydrogen at the 2 position of 1,3-diisopropylbenzene by a hydroxy group.	3.1	1	0	phenols	anticonvulsant; antiemetic; intravenous anaesthetic; radical scavenger; sedative
propranolol Propranolol: A widely used non-cardioselective beta-adrenergic antagonist. Propranolol has been used for MYOCARDIAL INFARCTION; ARRHYTHMIA; ANGINA PECTORIS; HYPERTENSION; HYPERTHYROIDISM; MIGRAINE; PHEOCHROMOCYTOMA; and ANXIETY but adverse effects instigate replacement by newer drugs.. propranolol : A propanolamine that is propan-2-ol substituted by a propan-2-ylamino group at position 1 and a naphthalen-1-yloxy group at position 3.	4.79	10	0	naphthalenes; propanolamine; secondary amine	anti-arrhythmia drug; antihypertensive agent; anxiolytic drug; beta-adrenergic antagonist; environmental contaminant; human blood serum metabolite; vasodilator agent; xenobiotic
propyl gallate Propyl Gallate: Antioxidant for foods, fats, oils, ethers, emulsions, waxes, and transformer oils.	8.39	110	0	trihydroxybenzoic acid
pyrilamine Pyrilamine: A histamine H1 antagonist. It has mild hypnotic properties and some local anesthetic action and is used for allergies (including skin eruptions) both parenterally and locally. It is a common ingredient of cold remedies.. mepyramine : An ethylenediamine derivative that is ethylenediamine in which one of the amino nitrogens is substituted by two methyl groups and the remaining amino nitrogen is substituted by a 4-methoxybenzyl and a pyridin-2-yl group.	3.79	3	0	aromatic ether; ethylenediamine derivative	H1-receptor antagonist
1,2,5,8-tetrahydroxy anthraquinone 1,2,5,8-tetrahydroxy anthraquinone: structure in first source. quinalizarin : A tetrahydroxyanthraquinone having the four hydroxy groups at the 1-, 2-, 5- and 8-positions.	3.53	2	0	tetrahydroxyanthraquinone	EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor
ranitidine [no description available]	2.1	1	0	aralkylamine
resorcinol resorcinol: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7951. resorcinol : A benzenediol that is benzene dihydroxylated at positions 1 and 3.	3.53	8	0	benzenediol; phenolic donor; resorcinols	erythropoietin inhibitor; sensitiser
1,6-bis(cyclohexyloximinocarbonyl)hexane 1,6-bis(cyclohexyloximinocarbonyl)hexane: selective inhibitor of canine platelet diglyceride lipase	2	1	0	carbamate ester; organonitrogen compound
risperidone Risperidone: A selective blocker of DOPAMINE D2 RECEPTORS and SEROTONIN 5-HT2 RECEPTORS that acts as an atypical antipsychotic agent. It has been shown to improve both positive and negative symptoms in the treatment of SCHIZOPHRENIA.. risperidone : A member of the class of pyridopyrimidines that is 2-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one carrying an additional 2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl group at position 2.	2.1	1	0	1,2-benzoxazoles; heteroarylpiperidine; organofluorine compound; pyridopyrimidine	alpha-adrenergic antagonist; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; H1-receptor antagonist; psychotropic drug; second generation antipsychotic; serotonergic antagonist
ro 31-8220 Ro 31-8220: a protein kinase C inhibitor	2.01	1	0	imidothiocarbamic ester; indoles; maleimides	EC 2.7.11.13 (protein kinase C) inhibitor
rofecoxib [no description available]	2.01	1	0	butenolide; sulfone	analgesic; cyclooxygenase 2 inhibitor; non-steroidal anti-inflammatory drug
rolipram [no description available]	1.98	1	0	pyrrolidin-2-ones	antidepressant; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor
4-bromotetramisole 4-bromotetramisole: available in levo & dextro form; L-form potent inhibitor of non specific alkaline phosphatase; RN given refers to cpd without isomeric designation	2	1	0
salicylamide salamide: a major impurity of hydrochlorothiazide; structure in first source	3.52	2	0	phenols; salicylamides	antirheumatic drug; non-narcotic analgesic
sanguinarine benzophenanthridine alkaloid : A specific group of isoquinoline alkaloids that occur only in higher plants and are constituents mainly of the Papaveraceae family.	1.99	1	0	alkaloid antibiotic; benzophenanthridine alkaloid; botanical anti-fungal agent
sennoside a&b [no description available]	3.41	1	1
sulfadiazine Sulfadiazine: One of the short-acting SULFONAMIDES used in combination with PYRIMETHAMINE to treat toxoplasmosis in patients with acquired immunodeficiency syndrome and in newborns with congenital infections.. sulfadiazine : A sulfonamide consisting of pyrimidine with a 4-aminobenzenesulfonamido group at the 2-position.. diazine : The parent structure of the diazines.	2.21	1	0	pyrimidines; substituted aniline; sulfonamide antibiotic; sulfonamide	antiinfective agent; antimicrobial agent; antiprotozoal drug; coccidiostat; drug allergen; EC 1.1.1.153 [sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming)] inhibitor; EC 2.5.1.15 (dihydropteroate synthase) inhibitor; environmental contaminant; xenobiotic
linsidomine linsidomine: RN given refers to parent cpd; structure	2.01	1	0	morpholines
sodium fluoride [no description available]	4.85	12	0	fluoride salt	mutagen
sotalol Sotalol: An adrenergic beta-antagonist that is used in the treatment of life-threatening arrhythmias.. sotalol : A sulfonamide that is N-phenylmethanesulfonamide in which the phenyl group is substituted at position 4 by a 1-hydroxy-2-(isopropylamino)ethyl group. It has both beta-adrenoreceptor blocking (Vaughan Williams Class II) and cardiac action potential duration prolongation (Vaughan Williams Class III) antiarrhythmic properties. It is used (usually as the hydrochloride salt) for the management of ventricular and supraventricular arrhythmias.	2.1	1	0	ethanolamines; secondary alcohol; secondary amino compound; sulfonamide	anti-arrhythmia drug; beta-adrenergic antagonist; environmental contaminant; xenobiotic
stearic acid octadecanoic acid : A C18 straight-chain saturated fatty acid component of many animal and vegetable lipids. As well as in the diet, it is used in hardening soaps, softening plastics and in making cosmetics, candles and plastics.	7.77	3	0	long-chain fatty acid; saturated fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; human metabolite; plant metabolite
sulfadimethoxine Sulfadimethoxine: A sulfanilamide that is used as an anti-infective agent.. sulfadimethoxine : A sulfonamide consisting of pyrimidine having methoxy substituents at the 2- and 6-positions and a 4-aminobenzenesulfonamido group at the 4-position.	3.1	1	0	aromatic ether; pyrimidines; substituted aniline; sulfonamide antibiotic; sulfonamide	antiinfective agent; antimicrobial agent; drug allergen; environmental contaminant; xenobiotic
sulfamethoxazole Sulfamethoxazole: A bacteriostatic antibacterial agent that interferes with folic acid synthesis in susceptible bacteria. Its broad spectrum of activity has been limited by the development of resistance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p208). sulfamethoxazole : An isoxazole (1,2-oxazole) compound having a methyl substituent at the 5-position and a 4-aminobenzenesulfonamido group at the 3-position.	3.27	5	0	isoxazoles; substituted aniline; sulfonamide antibiotic; sulfonamide	antibacterial agent; antiinfective agent; antimicrobial agent; drug allergen; EC 1.1.1.153 [sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming)] inhibitor; EC 2.5.1.15 (dihydropteroate synthase) inhibitor; environmental contaminant; epitope; P450 inhibitor; xenobiotic
sulfapyridine Sulfapyridine: Antibacterial, potentially toxic, used to treat certain skin diseases.. sulfapyridine : A sulfonamide consisting of pyridine with a 4-aminobenzenesulfonamido group at the 2-position.	1.98	1	0	pyridines; substituted aniline; sulfonamide antibiotic; sulfonamide	antiinfective agent; dermatologic drug; drug allergen; environmental contaminant; xenobiotic
sulfasalazine Sulfasalazine: A drug that is used in the management of inflammatory bowel diseases. Its activity is generally considered to lie in its metabolic breakdown product, 5-aminosalicylic acid (see MESALAMINE) released in the colon. (From Martindale, The Extra Pharmacopoeia, 30th ed, p907). sulfasalazine : An azobenzene consisting of diphenyldiazene having a carboxy substituent at the 4-position, a hydroxy substituent at the 3-position and a 2-pyridylaminosulphonyl substituent at the 4'-position.	2.69	3	0
sulfathiazole Sulfathiazole: A sulfathiazole compound that is used as a short-acting anti-infective agent. It is no longer commonly used systemically due to its toxicity, but may still be applied topically in combination with other drugs for the treatment of vaginal and skin infections, and is still used in veterinary medicine.. sulfathiazole : A 1,3-thiazole compound having a 4-aminobenzenesulfonamido group at the 2-position.	3.1	1	0	1,3-thiazoles; substituted aniline; sulfonamide antibiotic; sulfonamide	antiinfective agent; drug allergen; EC 2.5.1.15 (dihydropteroate synthase) inhibitor; environmental contaminant; xenobiotic
sulfinpyrazone Sulfinpyrazone: A uricosuric drug that is used to reduce the serum urate levels in gout therapy. It lacks anti-inflammatory, analgesic, and diuretic properties.	3.1	1	0	pyrazolidines; sulfoxide	uricosuric drug
sulfobromophthalein Sulfobromophthalein: A phenolphthalein that is used as a diagnostic aid in hepatic function determination.	1.95	1	0	2-benzofurans; organobromine compound; organosulfonic acid; phenols	dye
sulforaphane sulforaphane: from Cardaria draba L.. sulforaphane : An isothiocyanate having a 4-(methylsulfinyl)butyl group attached to the nitrogen.	7.17	1	0	isothiocyanate; sulfoxide	antineoplastic agent; antioxidant; EC 3.5.1.98 (histone deacetylase) inhibitor; plant metabolite
sumatriptan Sumatriptan: A serotonin agonist that acts selectively at 5HT1 receptors. It is used in the treatment of MIGRAINE DISORDERS.. sumatriptan : A sulfonamide that consists of N,N-dimethyltryptamine bearing an additional (N-methylsulfamoyl)methyl substituent at position 5. Selective agonist for a vascular 5-HT1 receptor subtype (probably a member of the 5-HT1D family). Used (in the form of its succinate salt) for the acute treatment of migraine with or without aura in adults.	2.1	1	0	sulfonamide; tryptamines	serotonergic agonist; vasoconstrictor agent
suprofen Suprofen: An IBUPROFEN-type anti-inflammatory analgesic and antipyretic. It inhibits prostaglandin synthesis and has been proposed as an anti-arthritic.. suprofen : An aromatic ketone that is thiophene substituted at C-2 by a 4-(1-carboxyethyl)benzoyl group.	3.54	2	0	aromatic ketone; monocarboxylic acid; thiophenes	antirheumatic drug; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; peripheral nervous system drug
suramin Suramin: A polyanionic compound with an unknown mechanism of action. It is used parenterally in the treatment of African trypanosomiasis and it has been used clinically with diethylcarbamazine to kill the adult Onchocerca. (From AMA Drug Evaluations Annual, 1992, p1643) It has also been shown to have potent antineoplastic properties.. suramin : A member of the class of phenylureas that is urea in which each of the amino groups has been substituted by a 3-({2-methyl-5-[(4,6,8-trisulfo-1-naphthyl)carbamoyl]phenyl}carbamoyl)phenyl group. An activator of both the rabbit skeletal muscle RyR1 and sheep cardiac RyR2 isoform ryanodine receptor channels, it has been used for the treatment of human African trypanosomiasis for over 100 years.	3.1	5	0	naphthalenesulfonic acid; phenylureas; secondary carboxamide	angiogenesis inhibitor; antinematodal drug; antineoplastic agent; apoptosis inhibitor; EC 2.7.11.13 (protein kinase C) inhibitor; GABA antagonist; GABA-gated chloride channel antagonist; purinergic receptor P2 antagonist; ryanodine receptor agonist; trypanocidal drug
talipexole talipexole: dopamine receptor agonist; structure given in first source	2.38	2	0	azepine
gatifloxacin Gatifloxacin: A fluoroquinolone antibacterial agent and DNA TOPOISOMERASE II inhibitor that is used as an ophthalmic solution for the treatment of BACTERIAL CONJUNCTIVITIS.. gatifloxacin : A monocarboxylic acid that is 4-oxo-1,4-dihydroquinoline-3-carboxylic acid which is substituted on the nitrogen by a cyclopropyl group and at positions 6, 7, and 8 by fluoro, 3-methylpiperazin-1-yl, and methoxy groups, respectively. Gatifloxacin is an antibiotic of the fourth-generation fluoroquinolone family, that like other members of that family, inhibits the bacterial topoisomerase type-II enzymes.	2.1	1	0	N-arylpiperazine; organofluorine compound; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone	antiinfective agent; antimicrobial agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
temazepam Temazepam: A benzodiazepine that acts as a GAMMA-AMINOBUTYRIC ACID modulator and anti-anxiety agent.	3.1	1	0	benzodiazepine
temozolomide [no description available]	2.21	1	0	imidazotetrazine; monocarboxylic acid amide; triazene derivative	alkylating agent; antineoplastic agent; prodrug
terbutaline Terbutaline: A selective beta-2 adrenergic agonist used as a bronchodilator and tocolytic.. terbutaline : A member of the class of phenylethanolamines that is catechol substituted at position 5 by a 2-(tert-butylamino)-1-hydroxyethyl group.	2.1	1	0	phenylethanolamines; resorcinols	anti-asthmatic drug; beta-adrenergic agonist; bronchodilator agent; EC 3.1.1.7 (acetylcholinesterase) inhibitor; hypoglycemic agent; sympathomimetic agent; tocolytic agent
terfenadine Terfenadine: A selective histamine H1-receptor antagonist devoid of central nervous system depressant activity. The drug was used for ALLERGY but withdrawn due to causing LONG QT SYNDROME.	3.54	2	0	diarylmethane
tetracaine Tetracaine: A potent local anesthetic of the ester type used for surface and spinal anesthesia.. tetracaine : A benzoate ester in which 4-N-butylbenzoic acid and 2-(dimethylamino)ethanol have combined to form the ester bond; a local ester anaesthetic (ester caine) used for surface and spinal anaesthesia.	2.91	4	0	benzoate ester; tertiary amino compound	local anaesthetic
tetraethylammonium Tetraethylammonium: A potassium-selective ion channel blocker. (From J Gen Phys 1994;104(1):173-90)	2.69	3	0	quaternary ammonium ion
theobromine Theobromine: 3,7-Dimethylxanthine. The principle alkaloid in Theobroma cacao (the cacao bean) and other plants. A xanthine alkaloid that is used as a bronchodilator and as a vasodilator. It has a weaker diuretic activity than THEOPHYLLINE and is also a less powerful stimulant of smooth muscle. It has practically no stimulant effect on the central nervous system. It was formerly used as a diuretic and in the treatment of angina pectoris and hypertension. (From Martindale, The Extra Pharmacopoeia, 30th ed, pp1318-9). theobromine : A dimethylxanthine having the two methyl groups located at positions 3 and 7. A purine alkaloid derived from the cacao plant, it is found in chocolate, as well as in a number of other foods, and is a vasodilator, diuretic and heart stimulator.	2.96	4	0	dimethylxanthine	adenosine receptor antagonist; bronchodilator agent; food component; human blood serum metabolite; mouse metabolite; plant metabolite; vasodilator agent
thiotepa Thiotepa: A very toxic alkylating antineoplastic agent also used as an insect sterilant. It causes skin, gastrointestinal, CNS, and bone marrow damage. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), thiotepa may reasonably be anticipated to be a carcinogen (Merck Index, 11th ed).	1.94	1	0	aziridines
thiram Thiram: A dithiocarbamate chemical, used commercially in the rubber processing industry and as a fungicide. In vivo studies indicate that it inactivates the enzyme GLUTATHIONE REDUCTASE. It has mutagenic activity and may induce chromosomal aberrations.. thiram : An organic disulfide that results from the formal oxidative dimerisation of N,N-dimethyldithiocarbamic acid. It is widely used as a fungicidal seed treatment.	1.95	1	0	organic disulfide	antibacterial drug; antifungal agrochemical; antiseptic drug
thonzylamine thonzylamine: major descriptor (72-84); file-maintained to PYRIMIDINES	3.1	1	0	methoxybenzenes
tiaprofenic acid tiaprofenic acid: RN given refers to parent cpd; structure. tiaprofenic acid : An aromatic ketone that is thiophene substituted at C-2 by benzoyl and at C-4 by a 1-carboxyethyl group.	3.1	1	0	aromatic ketone; monocarboxylic acid; thiophenes	drug allergen; non-steroidal anti-inflammatory drug
tiopronin Tiopronin: Sulfhydryl acylated derivative of GLYCINE.	1.95	1	0	N-acyl-amino acid
8-(n,n-diethylamino)octyl-3,4,5-trimethoxybenzoate 8-(N,N-diethylamino)octyl-3,4,5-trimethoxybenzoate: intracellular calcium antagonist; RN given refers to parent cpd	9.55	556	0	trihydroxybenzoic acid
tolazoline Tolazoline: A vasodilator that apparently has direct actions on blood vessels and also increases cardiac output. Tolazoline can interact to some degree with histamine, adrenergic, and cholinergic receptors, but the mechanisms of its therapeutic effects are not clear. It is used in treatment of persistent pulmonary hypertension of the newborn.. tolazoline : A member of the class of imidazoles that is 4,5-dihydro-1H-imidazole substituted by a benzyl group.	1.96	1	0	imidazoles	alpha-adrenergic antagonist; antihypertensive agent; vasodilator agent
tolmetin Tolmetin: A non-steroidal anti-inflammatory agent (ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL) similar in mode of action to INDOMETHACIN.. tolmetin : A monocarboxylic acid that is (1-methylpyrrol-2-yl)acetic acid substituted at position 5 on the pyrrole ring by a 4-methylbenzoyl group. Used in the form of its sodium salt dihydrate as a nonselective nonsteroidal anti-inflammatory drug.	2.1	1	0	aromatic ketone; monocarboxylic acid; pyrroles	EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-steroidal anti-inflammatory drug
trazodone Trazodone: A serotonin uptake inhibitor that is used as an antidepressive agent. It has been shown to be effective in patients with major depressive disorders and other subsets of depressive disorders. It is generally more useful in depressive disorders associated with insomnia and anxiety. This drug does not aggravate psychotic symptoms in patients with schizophrenia or schizoaffective disorders. (From AMA Drug Evaluations Annual, 1994, p309). trazodone : An N-arylpiperazine in which one nitrogen is substituted by a 3-chlorophenyl group, while the other is substituted by a 3-(3-oxo[1,2,4]triazolo[4,3-a]pyridin-2(3H)-yl)propyl group.	2.1	1	0	monochlorobenzenes; N-alkylpiperazine; N-arylpiperazine; triazolopyridine	adrenergic antagonist; antidepressant; anxiolytic drug; H1-receptor antagonist; sedative; serotonin uptake inhibitor
triclosan [no description available]	2.49	2	0	aromatic ether; dichlorobenzene; monochlorobenzenes; phenols	antibacterial agent; antimalarial; drug allergen; EC 1.3.1.9 [enoyl-[acyl-carrier-protein] reductase (NADH)] inhibitor; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; fungicide; persistent organic pollutant; xenobiotic
trifluoperazine [no description available]	6.31	50	0	N-alkylpiperazine; N-methylpiperazine; organofluorine compound; phenothiazines	antiemetic; calmodulin antagonist; dopaminergic antagonist; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor; EC 5.3.3.5 (cholestenol Delta-isomerase) inhibitor; phenothiazine antipsychotic drug
triflupromazine Triflupromazine: A phenothiazine used as an antipsychotic agent and as an antiemetic.. triflupromazine : A member of the class of phenothiazines that is 10H-phenothiazine having a trifluoromethyl subsitituent at the 2-position and a 3-(dimethylamino)propyl group at the N-10 position.	3.1	1	0	organofluorine compound; phenothiazines; tertiary amine	anticoronaviral agent; antiemetic; dopaminergic antagonist; first generation antipsychotic
trimeprazine Trimeprazine: A phenothiazine derivative that is used as an antipruritic.	2.1	1	0	phenothiazines
trimethadione Trimethadione: An anticonvulsant effective in absence seizures, but generally reserved for refractory cases because of its toxicity. (From AMA Drug Evaluations Annual, 1994, p378). trimethadione : An oxazolidinone that is 1,3-oxazolidine-2,4-dione substituted by methyl groups at positions 3, 5 and 5. It is an antiepileptic agent.	2.15	1	0	oxazolidinone	anticonvulsant; geroprotector
trimethobenzamide trimethobenzamide: major descriptor (64-84); on-line search BENZAMIDES (64-84); Index Medicus search TRIMETHOBENZAMIDE (64-84); RN given refers to parent cpd. trimethobenzamide : The amide obtained by formal condensation of 3,4,5-trihydroxybenzoic acid with 4-[2-(N,N-dimethylamino)ethoxy]benzylamine. It is used to prevent nausea and vomitting in humans.	1.96	1	0	benzamides; tertiary amino compound	antiemetic
trimethoprim Trimethoprim: A pyrimidine inhibitor of dihydrofolate reductase, it is an antibacterial related to PYRIMETHAMINE. It is potentiated by SULFONAMIDES and the TRIMETHOPRIM, SULFAMETHOXAZOLE DRUG COMBINATION is the form most often used. It is sometimes used alone as an antimalarial. TRIMETHOPRIM RESISTANCE has been reported.. trimethoprim : An aminopyrimidine antibiotic whose structure consists of pyrimidine 2,4-diamine and 1,2,3-trimethoxybenzene moieties linked by a methylene bridge.	2.45	2	0	aminopyrimidine; methoxybenzenes	antibacterial drug; diuretic; drug allergen; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; environmental contaminant; xenobiotic
trimipramine Trimipramine: Tricyclic antidepressant similar to IMIPRAMINE, but with more antihistaminic and sedative properties.. trimipramine : A dibenzoazepine that is 10,11-dihydro-5H-dibenzo[b,f]azepine substituted by a 3-(dimethylamino)-2-methylpropyl group at the nitrogen atom. It is used as an antidepressant.	2.1	1	0	dibenzoazepine; tertiary amino compound	antidepressant; environmental contaminant; xenobiotic
tripelennamine Tripelennamine: A histamine H1 antagonist with low sedative action but frequent gastrointestinal irritation. It is used to treat ASTHMA; HAY FEVER; URTICARIA; and RHINITIS; and also in veterinary applications. Tripelennamine is administered by various routes, including topically.	3.1	1	0	aromatic amine
tyramine [no description available]	3	4	0	monoamine molecular messenger; primary amino compound; tyramines	EC 3.1.1.8 (cholinesterase) inhibitor; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter
urethane [no description available]	7.15	1	0	carbamate ester	fungal metabolite; mutagen
venlafaxine venlafaxine : A tertiary amino compound that is N,N-dimethylethanamine substituted at position 1 by a 1-hydroxycyclohexyl and 4-methoxyphenyl group.	2.1	1	0	cyclohexanols; monomethoxybenzene; tertiary alcohol; tertiary amino compound	adrenergic uptake inhibitor; analgesic; antidepressant; dopamine uptake inhibitor; environmental contaminant; serotonin uptake inhibitor; xenobiotic
w 7 W 7: RN given refers to parent cpd; structure; calmodulin antagonist	4.89	36	0
n,n-bis(3,4-dimethoxyphenethyl)-n-methylamine N,N-bis(3,4-dimethoxyphenethyl)-N-methylamine: structure given in first source	1.97	1	0	dimethoxybenzene
zomepirac zomepirac: RN given refers to parent cpd; structure	3.1	1	0	aromatic ketone; monocarboxylic acid; monochlorobenzenes; pyrroles	cardiovascular drug; non-steroidal anti-inflammatory drug
corticosterone [no description available]	4.6	8	0	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone	human metabolite; mouse metabolite
estriol hormonin: estrogen replacement; each tablet contains 600 ug micronized 17beta-estradiol, 270 ug estriol and 1.4 mg estrone. chlorapatite : A phosphate mineral with the formula Ca5(PO4)3Cl.	3.1	1	0	16alpha-hydroxy steroid; 17beta-hydroxy steroid; 3-hydroxy steroid	estrogen; human metabolite; human xenobiotic metabolite; mouse metabolite
reserpine Reserpine: An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria. Reserpine inhibits the uptake of norepinephrine into storage vesicles resulting in depletion of catecholamines and serotonin from central and peripheral axon terminals. It has been used as an antihypertensive and an antipsychotic as well as a research tool, but its adverse effects limit its clinical use.. reserpine : An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria.	3.07	5	0	alkaloid ester; methyl ester; yohimban alkaloid	adrenergic uptake inhibitor; antihypertensive agent; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; environmental contaminant; first generation antipsychotic; plant metabolite; xenobiotic
phentolamine Phentolamine: A nonselective alpha-adrenergic antagonist. It is used in the treatment of hypertension and hypertensive emergencies, pheochromocytoma, vasospasm of RAYNAUD DISEASE and frostbite, clonidine withdrawal syndrome, impotence, and peripheral vascular disease.. phentolamine : A substituted aniline that is 3-aminophenol in which the hydrogens of the amino group are replaced by 4-methylphenyl and 4,5-dihydro-1H-imidazol-2-ylmethyl groups respectively. An alpha-adrenergic antagonist, it is used for the treatment of hypertension.	1.96	1	0	imidazoles; phenols; substituted aniline; tertiary amino compound	alpha-adrenergic antagonist; vasodilator agent
6-methylthiopurine 6-methylthiopurine : A thiopurine that is 9H-purine substituted by a methylsulfanyl group at position 6.	1.98	1	0	thiopurine
sorbitol D-glucitol : The D-enantiomer of glucitol (also known as D-sorbitol).	3	4	0	glucitol	cathartic; Escherichia coli metabolite; food humectant; human metabolite; laxative; metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite; sweetening agent
alloxan Alloxan: Acidic compound formed by oxidation of URIC ACID. It is isolated as an efflorescent crystalline hydrate.. alloxan : A member of the class of pyrimidones, the structure of which is that of perhydropyrimidine substituted at C-2, -4, -5 and -6 by oxo groups.	7.1	1	0	pyrimidone	hyperglycemic agent; metabolite
thymidine [no description available]	2.37	2	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite
2-aminophenol [no description available]	3.1	1	0	aminophenol	bacterial metabolite
hydroxyproline Hydroxyproline: A hydroxylated form of the imino acid proline. A deficiency in ASCORBIC ACID can result in impaired hydroxyproline formation.. hydroxyproline : A proline derivative that is proline substituted by at least one hydroxy group.	2.77	3	0	4-hydroxyproline; L-alpha-amino acid zwitterion	human metabolite; mouse metabolite; plant metabolite
thyroxine Thyroxine: The major hormone derived from the thyroid gland. Thyroxine is synthesized via the iodination of tyrosines (MONOIODOTYROSINE) and the coupling of iodotyrosines (DIIODOTYROSINE) in the THYROGLOBULIN. Thyroxine is released from thyroglobulin by proteolysis and secreted into the blood. Thyroxine is peripherally deiodinated to form TRIIODOTHYRONINE which exerts a broad spectrum of stimulatory effects on cell metabolism.. thyroxine : An iodothyronine compound having iodo substituents at the 3-, 3'-, 5- and 5'-positions.	4.16	5	0	2-halophenol; iodophenol; L-phenylalanine derivative; non-proteinogenic L-alpha-amino acid; thyroxine zwitterion; thyroxine	antithyroid drug; human metabolite; mouse metabolite; thyroid hormone
dextroamphetamine Dextroamphetamine: The d-form of AMPHETAMINE. It is a central nervous system stimulant and a sympathomimetic. It has also been used in the treatment of narcolepsy and of attention deficit disorders and hyperactivity in children. Dextroamphetamine has multiple mechanisms of action including blocking uptake of adrenergics and dopamine, stimulating release of monamines, and inhibiting monoamine oxidase. It is also a drug of abuse and a psychotomimetic.. (S)-amphetamine : A 1-phenylpropan-2-amine that has S configuration.	2.1	1	0	1-phenylpropan-2-amine	adrenergic agent; adrenergic uptake inhibitor; dopamine uptake inhibitor; dopaminergic agent; neurotoxin; sympathomimetic agent
carbachol Carbachol: A slowly hydrolyzed CHOLINERGIC AGONIST that acts at both MUSCARINIC RECEPTORS and NICOTINIC RECEPTORS.	4.33	20	0	ammonium salt; carbamate ester	cardiotonic drug; miotic; muscarinic agonist; nicotinic acetylcholine receptor agonist; non-narcotic analgesic
aldosterone [no description available]	4.45	7	0	11beta-hydroxy steroid; 18-oxo steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid hormone; mineralocorticoid; primary alpha-hydroxy ketone; steroid aldehyde	human metabolite; mouse metabolite
penicillamine Penicillamine: 3-Mercapto-D-valine. The most characteristic degradation product of the penicillin antibiotics. It is used as an antirheumatic and as a chelating agent in Wilson's disease.. penicillamine : An alpha-amino acid having the structure of valine substituted at the beta position with a sulfanyl group.	3.12	5	0	non-proteinogenic alpha-amino acid; penicillamine	antirheumatic drug; chelator; copper chelator; drug allergen
tetrahydrocortisol [no description available]	3.1	1	0	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3alpha-hydroxy steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone
prednisone Prednisone: A synthetic anti-inflammatory glucocorticoid derived from CORTISONE. It is biologically inert and converted to PREDNISOLONE in the liver.. prednisone : A synthetic glucocorticoid drug that is particularly effective as an immunosuppressant, and affects virtually all of the immune system. Prednisone is a prodrug that is converted by the liver into prednisolone (a beta-hydroxy group instead of the oxo group at position 11), which is the active drug and also a steroid.	3.1	1	0	11-oxo steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	adrenergic agent; anti-inflammatory drug; antineoplastic agent; immunosuppressive agent; prodrug
tetrahydrocortisone [no description available]	3.1	1	0	21-hydroxy steroid
estrone Hydroxyestrones: Estrone derivatives substituted with one or more hydroxyl groups in any position. They are important metabolites of estrone and other estrogens.	3.56	2	0	17-oxo steroid; 3-hydroxy steroid; phenolic steroid; phenols	antineoplastic agent; bone density conservation agent; estrogen; human metabolite; mouse metabolite
androsterone [no description available]	3.1	1	0	17-oxo steroid; 3alpha-hydroxy steroid; androstanoid; C19-steroid	androgen; anticonvulsant; human blood serum metabolite; human metabolite; human urinary metabolite; mouse metabolite; pheromone
etiocholanolone Etiocholanolone: The 5-beta-reduced isomer of ANDROSTERONE. Etiocholanolone is a major metabolite of TESTOSTERONE and ANDROSTENEDIONE in many mammalian species including humans. It is excreted in the URINE.. 3alpha-hydroxy-5beta-androstan-17-one : An androstanoid that is 5beta-androstane substituted by an alpha-hydroxy group at position 3 and an oxo group at position 17. It is a metabolite of testosterone in mammals.	3.1	1	0	17-oxo steroid; 3alpha-hydroxy steroid; androstanoid	human metabolite; mouse metabolite
dehydroepiandrosterone Dehydroepiandrosterone: A major C19 steroid produced by the ADRENAL CORTEX. It is also produced in small quantities in the TESTIS and the OVARY. Dehydroepiandrosterone (DHEA) can be converted to TESTOSTERONE; ANDROSTENEDIONE; ESTRADIOL; and ESTRONE. Most of DHEA is sulfated (DEHYDROEPIANDROSTERONE SULFATE) before secretion.. dehydroepiandrosterone : An androstanoid that is androst-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 17. It is a naturally occurring steroid hormone produced by the adrenal glands.	3.1	1	0	17-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; androstanoid	androgen; human metabolite; mouse metabolite
hydroxyacetylaminofluorene Hydroxyacetylaminofluorene: A N-hydroxylated derivative of 2-ACETYLAMINOFLUORENE that has demonstrated carcinogenic action.	3.1	1	0	2-acetamidofluorenes
2-acetylaminofluorene 2-Acetylaminofluorene: A hepatic carcinogen whose mechanism of activation involves N-hydroxylation to the aryl hydroxamic acid followed by enzymatic sulfonation to sulfoxyfluorenylacetamide. It is used to study the carcinogenicity and mutagenicity of aromatic amines.	2.37	2	0	2-acetamidofluorenes	antimitotic; carcinogenic agent; epitope; mutagen
penicillin g Penicillin G: A penicillin derivative commonly used in the form of its sodium or potassium salts in the treatment of a variety of infections. It is effective against most gram-positive bacteria and against gram-negative cocci. It has also been used as an experimental convulsant because of its actions on GAMMA-AMINOBUTYRIC ACID mediated synaptic transmission.. benzylpenicillin : A penicillin in which the substituent at position 6 of the penam ring is a phenylacetamido group.	2.75	3	0	penicillin allergen; penicillin	antibacterial drug; drug allergen; epitope
pilocarpine Pilocarpine: A slowly hydrolyzed muscarinic agonist with no nicotinic effects. Pilocarpine is used as a miotic and in the treatment of glaucoma.. (+)-pilocarpine : The (+)-enantiomer of pilocarpine.	7.77	3	0	pilocarpine	antiglaucoma drug
dimethylphenylpiperazinium iodide Dimethylphenylpiperazinium Iodide: A selective nicotinic cholinergic agonist used as a research tool. DMPP activates nicotinic receptors in autonomic ganglia but has little effect at the neuromuscular junction.	2.38	2	0	N-arylpiperazine; organic iodide salt; piperazinium salt; quaternary ammonium salt	nicotinic acetylcholine receptor agonist
pentylenetetrazole Pentylenetetrazole: A pharmaceutical agent that displays activity as a central nervous system and respiratory stimulant. It is considered a non-competitive GAMMA-AMINOBUTYRIC ACID antagonist. Pentylenetetrazole has been used experimentally to study seizure phenomenon and to identify pharmaceuticals that may control seizure susceptibility.. pentetrazol : An organic heterobicyclic compound that is 1H-tetrazole in which the hydrogens at positions 1 and 5 are replaced by a pentane-1,5-diyl group. A central and respiratory stimulant, it was formerly used for the treatment of cough and other respiratory tract disorders, cardiovascular disorders including hypotension, and pruritis.	2.6	1	0	organic heterobicyclic compound; organonitrogen heterocyclic compound
triiodothyronine Triiodothyronine: A T3 thyroid hormone normally synthesized and secreted by the thyroid gland in much smaller quantities than thyroxine (T4). Most T3 is derived from peripheral monodeiodination of T4 at the 5' position of the outer ring of the iodothyronine nucleus. The hormone finally delivered and used by the tissues is mainly T3.. 3,3',5-triiodo-L-thyronine : An iodothyronine compound having iodo substituents at the 3-, 3'- and 5-positions. Although some is produced in the thyroid, most of the 3,3',5-triiodo-L-thyronine in the body is generated by mono-deiodination of L-thyroxine in the peripheral tissues. Its metabolic activity is about 3 to 5 times that of L-thyroxine. The sodium salt is used in the treatment of hypothyroidism.	3.54	2	0	2-halophenol; amino acid zwitterion; iodophenol; iodothyronine	human metabolite; mouse metabolite; thyroid hormone
diethylnitrosamine Diethylnitrosamine: A nitrosamine derivative with alkylating, carcinogenic, and mutagenic properties.. N-nitrosodiethylamine : A nitrosamine that is N-ethylethanamine substituted by a nitroso group at the N-atom.	8.3	6	0	nitrosamine	carcinogenic agent; hepatotoxic agent; mutagen
isonicotinic acid isonicotinic acid : A pyridinemonocarboxylic acid in which the carboxy group is at position 4 of the pyridine ring.	2.1	1	0	pyridinemonocarboxylic acid	algal metabolite; human metabolite
isoflurophate Isoflurophate: A di-isopropyl-fluorophosphate which is an irreversible cholinesterase inhibitor used to investigate the NERVOUS SYSTEM.	1.94	1	0	dialkyl phosphate
carbon tetrachloride Carbon Tetrachloride: A solvent for oils, fats, lacquers, varnishes, rubber waxes, and resins, and a starting material in the manufacturing of organic compounds. Poisoning by inhalation, ingestion or skin absorption is possible and may be fatal. (Merck Index, 11th ed). tetrachloromethane : A chlorocarbon that is methane in which all the hydrogens have been replaced by chloro groups.	4.39	21	0	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
alanine Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.	2.71	3	0	alanine zwitterion; alanine; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid	EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor; fundamental metabolite
serine Serine: A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids.. serine : An alpha-amino acid that is alanine substituted at position 3 by a hydroxy group.	2.68	3	0	L-alpha-amino acid; proteinogenic amino acid; serine family amino acid; serine zwitterion; serine	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
benz(a)anthracene benz(a)anthracene: 4 fused rings of which one is angular in contrast to the linear NAPHTHACENES. tetraphene : An angular ortho-fused polycyclic arene consisting of four fused benzene rings.	3.1	1	0	ortho-fused polycyclic arene; tetraphenes
4-nitroquinoline-1-oxide 4-nitroquinoline N-oxide : A quinoline N-oxide carrying a nitro substituent at position 4.	2.41	2	0	C-nitro compound; quinoline N-oxide	carcinogenic agent
chloramphenicol Amphenicol: Chloramphenicol and its derivatives.	4.33	6	0	C-nitro compound; carboxamide; diol; organochlorine compound	antibacterial drug; antimicrobial agent; Escherichia coli metabolite; geroprotector; Mycoplasma genitalium metabolite; protein synthesis inhibitor
aspartic acid Aspartic Acid: One of the non-essential amino acids commonly occurring in the L-form. It is found in animals and plants, especially in sugar cane and sugar beets. It may be a neurotransmitter.. aspartic acid : An alpha-amino acid that consists of succinic acid bearing a single alpha-amino substituent. L-aspartic acid : The L-enantiomer of aspartic acid.	2.1	1	0	aspartate family amino acid; aspartic acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; mouse metabolite; neurotransmitter
glutamine Glutamine: A non-essential amino acid present abundantly throughout the body and is involved in many metabolic processes. It is synthesized from GLUTAMIC ACID and AMMONIA. It is the principal carrier of NITROGEN in the body and is an important energy source for many cells.. L-glutamine : An optically active form of glutamine having L-configuration.. glutamine : An alpha-amino acid that consists of butyric acid bearing an amino substituent at position 2 and a carbamoyl substituent at position 4.	7.41	1	0	amino acid zwitterion; glutamine family amino acid; glutamine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	EC 1.14.13.39 (nitric oxide synthase) inhibitor; Escherichia coli metabolite; human metabolite; metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
lysine Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.	8.43	7	0	aspartate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; lysine; organic molecular entity; proteinogenic amino acid	algal metabolite; anticonvulsant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
cyanides Cyanides: Inorganic salts of HYDROGEN CYANIDE containing the -CN radical. The concept also includes isocyanides. It is distinguished from NITRILES, which denotes organic compounds containing the -CN radical.. cyanides : Salts and C-organyl derivatives of hydrogen cyanide, HC#N.. isocyanide : The isomer HN(+)#C(-) of hydrocyanic acid, HC#N, and its hydrocarbyl derivatives RNC (RN(+)#C(-)).. cyanide : A pseudohalide anion that is the conjugate base of hydrogen cyanide.	3.07	5	0	pseudohalide anion	EC 1.9.3.1 (cytochrome c oxidase) inhibitor
vincristine [no description available]	2.13	1	0	acetate ester; formamides; methyl ester; organic heteropentacyclic compound; organic heterotetracyclic compound; tertiary alcohol; tertiary amino compound; vinca alkaloid	antineoplastic agent; drug; microtubule-destabilising agent; plant metabolite; tubulin modulator
physostigmine Physostigmine: A cholinesterase inhibitor that is rapidly absorbed through membranes. It can be applied topically to the conjunctiva. It also can cross the blood-brain barrier and is used when central nervous system effects are desired, as in the treatment of severe anticholinergic toxicity.	2.1	1	0	carbamate ester; indole alkaloid	antidote to curare poisoning; EC 3.1.1.8 (cholinesterase) inhibitor; miotic
sucrose Saccharum: A plant genus of the family POACEAE widely cultivated in the tropics for the sweet cane that is processed into sugar.	8.96	12	0	glycosyl glycoside	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; sweetening agent
ethinyl estradiol Ethinyl Estradiol: A semisynthetic alkylated ESTRADIOL with a 17-alpha-ethinyl substitution. It has high estrogenic potency when administered orally, and is often used as the estrogenic component in ORAL CONTRACEPTIVES.. 17alpha-ethynylestradiol : A 3-hydroxy steroid that is estradiol substituted by a ethynyl group at position 17. It is a xenoestrogen synthesized from estradiol and has been shown to exhibit high estrogenic potency on oral administration.	3.49	2	0	17-hydroxy steroid; 3-hydroxy steroid; terminal acetylenic compound	xenoestrogen
tubocurarine Tubocurarine: A neuromuscular blocker and active ingredient in CURARE; plant based alkaloid of Menispermaceae.. tubocurarine : A benzylisoquinoline alkaloid muscle relaxant which constitutes the active component of curare.. isoquinoline alkaloid : Any alkaloid that has a structure based on an isoquinoline nucleus. They are derived from the amino acids like tyrosine and phenylalanine.	1.97	1	0	bisbenzylisoquinoline alkaloid	drug allergen; muscle relaxant; nicotinic antagonist
9,10-dimethyl-1,2-benzanthracene 9,10-Dimethyl-1,2-benzanthracene: Polycyclic aromatic hydrocarbon found in tobacco smoke that is a potent carcinogen.. 7,12-dimethyltetraphene : A tetraphene having methyl substituents at the 7- and 12-positions. It is a potent carcinogen and is present in tobacco smoke.	3.13	5	0	ortho-fused polycyclic arene; tetraphenes	carcinogenic agent
adenosine diphosphate Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.	4.87	8	1	adenosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	fundamental metabolite; human metabolite
2,3,4,6-tetrachlorophenol 2,3,4,6-tetrachlorophenol: RN given refers to parent cpd; see also record for tetrachlorophenol with locants for chloro groups not specified. 2,3,4,6-tetrachlorophenol : A tetrachlorophenol in which the chlorines are located at positions 2, 3, 4, and 6.	2.02	1	0	tetrachlorophenol	xenobiotic metabolite
uridine diphosphate Uridine Diphosphate: A uracil nucleotide containing a pyrophosphate group esterified to C5 of the sugar moiety.	2.41	1	0	pyrimidine ribonucleoside 5'-diphosphate; uridine 5'-phosphate	Escherichia coli metabolite; mouse metabolite
kanamycin a Kanamycin: Antibiotic complex produced by Streptomyces kanamyceticus from Japanese soil. Comprises 3 components: kanamycin A, the major component, and kanamycins B and C, the minor components.. kanamycin : Kanamycin is a naturally occurring antibiotic complex from Streptomyces kanamyceticus that consists of several components: kanamycin A, the major component (also usually designated as kanamycin), and kanamycins B, C, D and X the minor components.	2.08	1	0	kanamycins	bacterial metabolite
galactose galactopyranose : The pyranose form of galactose.	3.36	5	0	D-galactose; galactopyranose	Escherichia coli metabolite; mouse metabolite
carbostyril Quinolones: A group of derivatives of naphthyridine carboxylic acid, quinoline carboxylic acid, or NALIDIXIC ACID.. quinolin-2(1H)-one : A quinolone that is 1,2-dihydroquinoline substituted by an oxo group at position 2.	2.39	2	0	monohydroxyquinoline; quinolone	bacterial xenobiotic metabolite
phenylephrine Phenylephrine: An alpha-1 adrenergic agonist used as a mydriatic, nasal decongestant, and cardiotonic agent.. phenylephrine : A member of the class of the class of phenylethanolamines that is (1R)-2-(methylamino)-1-phenylethan-1-ol carrying an additional hydroxy substituent at position 3 on the phenyl ring.	3.7	10	0	phenols; phenylethanolamines; secondary amino compound	alpha-adrenergic agonist; cardiotonic drug; mydriatic agent; nasal decongestant; protective agent; sympathomimetic agent; vasoconstrictor agent
levodopa Levodopa: The naturally occurring form of DIHYDROXYPHENYLALANINE and the immediate precursor of DOPAMINE. Unlike dopamine itself, it can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to DOPAMINE. It is used for the treatment of PARKINSONIAN DISORDERS and is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system.. L-dopa : An optically active form of dopa having L-configuration. Used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease	2.71	3	0	amino acid zwitterion; dopa; L-tyrosine derivative; non-proteinogenic L-alpha-amino acid	allelochemical; antidyskinesia agent; antiparkinson drug; dopaminergic agent; hapten; human metabolite; mouse metabolite; neurotoxin; plant growth retardant; plant metabolite; prodrug
edetic acid Edetic Acid: A chelating agent that sequesters a variety of polyvalent cations such as CALCIUM. It is used in pharmaceutical manufacturing and as a food additive.	4.18	17	0	ethylenediamine derivative; polyamino carboxylic acid; tetracarboxylic acid	anticoagulant; antidote; chelator; copper chelator; geroprotector
phenylethyl alcohol Phenylethyl Alcohol: An antimicrobial, antiseptic, and disinfectant that is used also as an aromatic essence and preservative in pharmaceutics and perfumery.. 2-phenylethanol : A primary alcohol that is ethanol substituted by a phenyl group at position 2.	5.21	14	0	benzenes; primary alcohol	Aspergillus metabolite; fragrance; plant growth retardant; plant metabolite; Saccharomyces cerevisiae metabolite
tyrosine Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.	10.57	17	1	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; proteinogenic amino acid; tyrosine	EC 1.3.1.43 (arogenate dehydrogenase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
cysteamine Cysteamine: A mercaptoethylamine compound that is endogenously derived from the COENZYME A degradative pathway. The fact that cysteamine is readily transported into LYSOSOMES where it reacts with CYSTINE to form cysteine-cysteamine disulfide and CYSTEINE has led to its use in CYSTINE DEPLETING AGENTS for the treatment of CYSTINOSIS.. cysteamine : An amine that consists of an ethane skeleton substituted with a thiol group at C-1 and an amino group at C-2.	2.66	3	0	amine; thiol	geroprotector; human metabolite; mouse metabolite; radiation protective agent
phlorhizin [no description available]	2.69	3	0	aryl beta-D-glucoside; dihydrochalcones; monosaccharide derivative	antioxidant; plant metabolite
methoxamine Methoxamine: An alpha-1 adrenergic agonist that causes prolonged peripheral VASOCONSTRICTION.. methoxamine : An amphetamine in which the parent 1-phenylpropan-2-amine skeleton is substituted at position 1 with an hydroxy group and the phenyl ring is 2- and 5-substituted with methoxy groups. It is an antihypotensive agent (pressor), an agonist acting directly at alpha-adrenoceptors with selectivity for the alpha-1 adrenoceptor subtype similar to phenylephrine .	2.89	4	0	amphetamines	alpha-adrenergic agonist; antihypotensive agent
adenosine monophosphate Adenosine Monophosphate: Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position.	2.43	2	0	adenosine 5'-phosphate; purine ribonucleoside 5'-monophosphate	adenosine A1 receptor agonist; cofactor; EC 3.1.3.1 (alkaline phosphatase) inhibitor; EC 3.1.3.11 (fructose-bisphosphatase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
methicillin Methicillin: One of the PENICILLINS which is resistant to PENICILLINASE but susceptible to a penicillin-binding protein. It is inactivated by gastric acid so administered by injection.. methicillin : A penicillin that is 6-aminopenicillanic acid in which one of the amino hydrogens is replaced by a 2,6-dimethoxybenzoyl group.	2.05	1	0	penicillin allergen; penicillin	antibacterial drug
n-methyltryptamine N-methyltryptamine: RN given refers to parent cpd	2.17	1	0	tryptamine alkaloid; tryptamines	metabolite
methylene blue Methylene Blue: A compound consisting of dark green crystals or crystalline powder, having a bronze-like luster. Solutions in water or alcohol have a deep blue color. Methylene blue is used as a bacteriologic stain and as an indicator. It inhibits GUANYLATE CYCLASE, and has been used to treat cyanide poisoning and to lower levels of METHEMOGLOBIN.. methylene blue : An organic chloride salt having 3,7-bis(dimethylamino)phenothiazin-5-ium as the counterion. A commonly used dye that also exhibits antioxidant, antimalarial, antidepressant and cardioprotective properties.	3.05	5	0	organic chloride salt	acid-base indicator; antidepressant; antimalarial; antimicrobial agent; antioxidant; cardioprotective agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 4.6.1.2 (guanylate cyclase) inhibitor; fluorochrome; histological dye; neuroprotective agent; physical tracer
zoxazolamine Zoxazolamine: A uricosuric and muscle relaxant. Zoxazolamine acts centrally as a muscle relaxant, but the mechanism of its action is not understood.	1.99	1	0	benzoxazole
leucine Leucine: An essential branched-chain amino acid important for hemoglobin formation.. leucine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isobutyl group.	3.25	6	0	amino acid zwitterion; L-alpha-amino acid; leucine; proteinogenic amino acid; pyruvate family amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
berlition berlition: antioxidant preparation containing alpha-lipoic acid, used in the neuroprotective therapy of chronic brain ischemia for correction of free-radical processes. (R)-lipoic acid : The (R)-enantiomer of lipoic acid. A vitamin-like, C8 thia fatty acid with anti-oxidant properties.. lipoic acid : A heterocyclic thia fatty acid comprising pentanoic acid with a 1,2-dithiolan-3-yl group at the 5-position.	2.01	1	0	dithiolanes; heterocyclic fatty acid; lipoic acid; thia fatty acid	cofactor; nutraceutical; prosthetic group
aniline [no description available]	3.1	1	0	anilines; primary arylamine
dimethylnitrosamine Dimethylnitrosamine: A nitrosamine derivative with alkylating, carcinogenic, and mutagenic properties. It causes serious liver damage and is a hepatocarcinogen in rodents.	7.69	3	0	nitrosamine	geroprotector; mutagen
uridine triphosphate Uridine Triphosphate: Uridine 5'-(tetrahydrogen triphosphate). A uracil nucleotide containing three phosphate groups esterified to the sugar moiety.	2.4	2	0	pyrimidine ribonucleoside 5'-triphosphate; uridine 5'-phosphate	Escherichia coli metabolite; mouse metabolite
methionine Methionine: A sulfur-containing essential L-amino acid that is important in many body functions.. methionine : A sulfur-containing amino acid that is butyric acid bearing an amino substituent at position 2 and a methylthio substituent at position 4.	4.99	9	1	aspartate family amino acid; L-alpha-amino acid; methionine zwitterion; methionine; proteinogenic amino acid	antidote to paracetamol poisoning; human metabolite; micronutrient; mouse metabolite; nutraceutical
1,2-dipalmitoylphosphatidylcholine 1,2-Dipalmitoylphosphatidylcholine: Synthetic phospholipid used in liposomes and lipid bilayers to study biological membranes. It is also a major constituent of PULMONARY SURFACTANTS.	2.93	4	0
phenylalanine Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.	4.16	5	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; phenylalanine; proteinogenic amino acid	algal metabolite; EC 3.1.3.1 (alkaline phosphatase) inhibitor; Escherichia coli metabolite; human xenobiotic metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
desoxycorticosterone Desoxycorticosterone: A steroid metabolite that is the 11-deoxy derivative of CORTICOSTERONE and the 21-hydroxy derivative of PROGESTERONE	3.1	1	0	20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; mineralocorticoid; primary alpha-hydroxy ketone	human metabolite; mouse metabolite
colchicine (S)-colchicine : A colchicine that has (S)-configuration. It is a secondary metabolite, has anti-inflammatory properties and is used to treat gout, crystal-induced joint inflammation, familial Mediterranean fever, and many other conditions.	3.23	6	0	alkaloid; colchicine	anti-inflammatory agent; gout suppressant; mutagen
gallamine triethiodide Gallamine Triethiodide: A synthetic nondepolarizing blocking drug. The actions of gallamine triethiodide are similar to those of TUBOCURARINE, but this agent blocks the cardiac vagus and may cause sinus tachycardia and, occasionally, hypertension and increased cardiac output. It should be used cautiously in patients at risk from increased heart rate but may be preferred for patients with bradycardia. (From AMA Drug Evaluations Annual, 1992, p198)	2.39	2	0
cytidine [no description available]	2.45	2	0	cytidines	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
cytidine triphosphate Cytidine Triphosphate: Cytidine 5'-(tetrahydrogen triphosphate). A cytosine nucleotide containing three phosphate groups esterified to the sugar moiety.	2.03	1	0	cytidine 5'-phosphate; pyrimidine ribonucleoside 5'-triphosphate	Escherichia coli metabolite; mouse metabolite
oxacillin Oxacillin: An antibiotic similar to FLUCLOXACILLIN used in resistant staphylococci infections.. oxacillin : A penicillin antibiotic carrying a 5-methyl-3-phenylisoxazole-4-carboxamide group at position 6beta.	2.94	4	0	penicillin	antibacterial agent; antibacterial drug
cycloheximide Cycloheximide: Antibiotic substance isolated from streptomycin-producing strains of Streptomyces griseus. It acts by inhibiting elongation during protein synthesis.. cycloheximide : A dicarboximide that is 4-(2-hydroxyethyl)piperidine-2,6-dione in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 3,5-dimethyl-2-oxocyclohexyl group. It is an antibiotic produced by the bacterium Streptomyces griseus.	3.07	5	0	antibiotic fungicide; cyclic ketone; dicarboximide; piperidine antibiotic; piperidones; secondary alcohol	anticoronaviral agent; bacterial metabolite; ferroptosis inhibitor; neuroprotective agent; protein synthesis inhibitor
ficusin Ficusin: A naturally occurring furocoumarin, found in PSORALEA. After photoactivation with UV radiation, it binds DNA via single and double-stranded cross-linking.. psoralen : The simplest member of the class of psoralens that is 7H-furo[3,2-g]chromene having a keto group at position 7. It has been found in plants like Psoralea corylifolia and Ficus salicifolia.	2	1	0	psoralens	plant metabolite
egtazic acid Egtazic Acid: A chelating agent relatively more specific for calcium and less toxic than EDETIC ACID.. ethylene glycol bis(2-aminoethyl)tetraacetic acid : A diether that is ethylene glycol in which the hydrogens of the hydroxy groups have been replaced by 2-[bis(carboxymethyl)amino]ethyl group respectively.	5.64	77	0	diether; tertiary amino compound; tetracarboxylic acid	chelator
chloroform Chloroform: A commonly used laboratory solvent. It was previously used as an anesthetic, but was banned from use in the U.S. due to its suspected carcinogenicity.. chloroform : A one-carbon compound that is methane in which three of the hydrogens are replaced by chlorines.	3.4	7	0	chloromethanes; one-carbon compound	carcinogenic agent; central nervous system drug; inhalation anaesthetic; non-polar solvent; refrigerant
sodium citrate, anhydrous Sodium Citrate: Sodium salts of citric acid that are used as buffers and food preservatives. They are used medically as anticoagulants in stored blood, and for urine alkalization in the prevention of KIDNEY STONES.. sodium citrate : The trisodium salt of citric acid.	2.6	1	0	organic sodium salt	anticoagulant; flavouring agent
norethindrone Norethindrone: A synthetic progestational hormone with actions similar to those of PROGESTERONE but functioning as a more potent inhibitor of ovulation. It has weak estrogenic and androgenic properties. The hormone has been used in treating amenorrhea, functional uterine bleeding, endometriosis, and for CONTRACEPTION.. norethisterone : A 17beta-hydroxy steroid that is testosterone in which the hydrogen at position 17 is replaced by an ethynyl group and in which the methyl group attached to position 10 is replaced by hydrogen.	3.1	1	0	17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; terminal acetylenic compound; tertiary alcohol	progestin; synthetic oral contraceptive
norethynodrel Norethynodrel: A synthetic progestational hormone with actions and uses similar to those of PROGESTERONE. It has been used in the treatment of functional uterine bleeding and ENDOMETRIOSIS. As a contraceptive (CONTRACEPTIVE AGENTS), it has usually been administered in combination with MESTRANOL.	3.1	1	0	oxo steroid
17-alpha-hydroxyprogesterone 17alpha-hydroxyprogesterone : A 17alpha-hydroxy steroid that is the 17alpha-hydroxy derivative of progesterone.	3.1	1	0	17alpha-hydroxy-C21-steroid; 17alpha-hydroxy steroid; tertiary alpha-hydroxy ketone	human metabolite; metabolite; mouse metabolite; progestin
chlorisondamine Chlorisondamine: A nicotinic antagonist used primarily as a ganglionic blocker in animal research. It has been used as an antihypertensive agent but has been supplanted by more specific drugs in most clinical applications.	2.03	1	0	isoindoles
tubercidin Tubercidin: An antibiotic purine ribonucleoside that readily substitutes for adenosine in the biological system, but its incorporation into DNA and RNA has an inhibitory effect on the metabolism of these nucleic acids.. tubercidin : An N-glycosylpyrrolopyrimidine that is adenosine in which the in the 5-membered ring that is not attached to the ribose moiety is replaced by a carbon. Tubercidin is produced in the culture broth of Streptomyces tubericidus.	2.37	2	0	antibiotic antifungal agent; N-glycosylpyrrolopyrimidine; ribonucleoside	antimetabolite; antineoplastic agent; bacterial metabolite
ampicillin Ampicillin: Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic.. ampicillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-phenylacetamido group.	9.08	4	0	beta-lactam antibiotic; penicillin allergen; penicillin	antibacterial drug
mannitol [no description available]	3.1	5	0	mannitol	allergen; antiglaucoma drug; compatible osmolytes; Escherichia coli metabolite; food anticaking agent; food bulking agent; food humectant; food stabiliser; food thickening agent; hapten; metabolite; osmotic diuretic; sweetening agent
cytarabine [no description available]	2.06	1	0	beta-D-arabinoside; monosaccharide derivative; pyrimidine nucleoside	antimetabolite; antineoplastic agent; antiviral agent; immunosuppressive agent
ornithine Ornithine: An amino acid produced in the urea cycle by the splitting off of urea from arginine.. ornithine : An alpha-amino acid that is pentanoic acid bearing two amino substituents at positions 2 and 5.	1.94	1	0	non-proteinogenic L-alpha-amino acid; ornithine	algal metabolite; hepatoprotective agent; mouse metabolite
asparagine Asparagine: A non-essential amino acid that is involved in the metabolic control of cell functions in nerve and brain tissue. It is biosynthesized from ASPARTIC ACID and AMMONIA by asparagine synthetase. (From Concise Encyclopedia Biochemistry and Molecular Biology, 3rd ed). asparagine : An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 2-amino-2-oxoethyl group.	1.94	1	0	amino acid zwitterion; asparagine; aspartate family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
histidine Histidine: An essential amino acid that is required for the production of HISTAMINE.. L-histidine : The L-enantiomer of the amino acid histidine.. histidine : An alpha-amino acid that is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3.	2.67	3	0	amino acid zwitterion; histidine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
n-pentanol n-pentanol: RN given refers to parent cpd. pentan-1-ol : A short-chain primary fatty alcohol that is pentane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It has been isolated from Melicope ptelefolia.	2.15	1	0	pentanol; short-chain primary fatty alcohol	human metabolite; plant metabolite
valine Valine: A branched-chain essential amino acid that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway.. valine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isopropyl group.. L-valine : The L-enantiomer of valine.	2.37	2	0	L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid; valine	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
threonine Threonine: An essential amino acid occurring naturally in the L-form, which is the active form. It is found in eggs, milk, gelatin, and other proteins.. threonine : An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 1-hydroxyethyl group.	1.94	1	0	amino acid zwitterion; aspartate family amino acid; L-alpha-amino acid; proteinogenic amino acid; threonine	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
alizarin [no description available]	3.52	2	0	dihydroxyanthraquinone	chromophore; dye; plant metabolite
tryptophan Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3.	3.53	8	0	erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; tryptophan zwitterion; tryptophan	antidepressant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
n,n'-diphenyl-4-phenylenediamine N,N'-diphenyl-4-phenylenediamine: in veterinary medicine, has been used to prevent vitamin E deficiency in lambs; structure. N,N'-diphenyl-1,4-phenylenediamine : An N-substituted diamine that is 1,4-phenylenediamine in which one hydrogen from each amino group is replaced by a phenyl group.	1.96	1	0	N-substituted diamine; secondary amino compound	antioxidant
arginine Arginine: An essential amino acid that is physiologically active in the L-form.. arginine : An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group.	4.3	18	0	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
methyl bromide methyl bromide: used in ionization chambers, degreasing wool, extracting oils; insect fumigant; high concentrations can produce pulmonary edema,narcosis; chronic exposure can cause CNS depression,kidney injury; RN given refers to parent cpd; structure. bromomethane : A one-carbon compound in which the carbon is attached by single bonds to three hydrogen atoms and one bromine atom. It is produced naturally by marine algae.	2.25	1	0	bromohydrocarbon; bromomethanes; methyl halides	algal metabolite; fumigant insecticide; marine metabolite
ethylene Plastipore: high density polyethylene sponge biocompatible material; used as posts in dental bridges	1.97	1	0	alkene; gas molecular entity	plant hormone; refrigerant
acetylene [no description available]	2.41	1	0	alkyne; gas molecular entity; terminal acetylenic compound
methyl chloride Methyl Chloride: A hydrocarbon used as an industrial solvent. It has been used as an aerosal propellent, as a refrigerant and as a local anesthetic. (From Martindale, The Extra Pharmacopoeia, 31st ed, p1403). chlorocarbon : Compounds consisting wholly of chlorine and carbon.. chloromethane : A one-carbon compound that is methane in which one of the hydrogens is replaced by a chloro group.	2.44	2	0	chloromethanes; methyl halides	marine metabolite; mutagen; refrigerant
methylamine methyl group : An alkyl group that is the univalent group derived from methane by removal of a hydrogen atom.	2.37	2	0	methylamines; one-carbon compound; primary aliphatic amine	mouse metabolite
ethylamine ethylamine : A two-carbon primary aliphatic amine.	2.1	1	0	primary aliphatic amine	human metabolite
acetonitrile acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.	8.23	5	0	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
tert-butylhydroperoxide tert-Butylhydroperoxide: A direct-acting oxidative stress-inducing agent used to examine the effects of oxidant stress on Ca(2+)-dependent signal transduction in vascular endothelial cells. It is also used as a catalyst in polymerization reactions and to introduce peroxy groups into organic molecules.. tert-butyl hydroperoxide : An alkyl hydroperoxide in which the alkyl group is tert-butyl. It is widely used in a variety of oxidation processes.	2.44	2	0	alkyl hydroperoxide	antibacterial agent; oxidising agent
phencyclidine Phencyclidine: A hallucinogen formerly used as a veterinary anesthetic, and briefly as a general anesthetic for humans. Phencyclidine is similar to KETAMINE in structure and in many of its effects. Like ketamine, it can produce a dissociative state. It exerts its pharmacological action through inhibition of NMDA receptors (RECEPTORS, N-METHYL-D-ASPARTATE). As a drug of abuse, it is known as PCP and Angel Dust.. phencyclidine : A member of the class of piperidines that is piperidine in which the nitrogen is substituted with a 1-phenylcyclohexyl group. Formerly used as an anaesthetic agent, it exhibits both hallucinogenic and neurotoxic effects.	3.55	8	0	benzenes; piperidines	anaesthetic; neurotoxin; NMDA receptor antagonist; psychotropic drug
divinyl sulfone divinyl sulfone: cross-linking reagent for agarose gels. divinyl sulfone : A sulfone compound having two S-vinyl substituents.	2.1	1	0	sulfone	cross-linking reagent
tromethamine Tromethamine: An organic amine proton acceptor. It is used in the synthesis of surface-active agents and pharmaceuticals; as an emulsifying agent for cosmetic creams and lotions, mineral oil and paraffin wax emulsions, as a biological buffer, and used as an alkalizer. (From Merck, 11th ed; Martindale, The Extra Pharmacopoeia, 30th ed, p1424)	2.1	1	0	primary amino compound; triol	buffer
quinic acid (-)-quinic acid : The (-)-enantiomer of quinic acid.	4.87	33	0
tetraethoxysilane [no description available]	2.15	1	0
triparanol Triparanol: Antilipemic agent with high ophthalmic toxicity. According to Merck Index, 11th ed, the compound was withdrawn from the market in 1962 because of its association with the formation of irreversible cataracts.	1.95	1	0	stilbenoid	anticoronaviral agent
linalool linalool: RN given refers to parent cpd without isomeric designation; structure. linalool : A monoterpenoid that is octa-1,6-diene substituted by methyl groups at positions 3 and 7 and a hydroxy group at position 3. It has been isolated from plants like Ocimum canum.	4.09	4	0	monoterpenoid; tertiary alcohol	antimicrobial agent; fragrance; plant metabolite; volatile oil component
acrylic acid acrylic acid: RN given refers to parent cpd. acrylic acid : A alpha,beta-unsaturated monocarboxylic acid that is ethene substituted by a carboxy group.	2.25	1	0	alpha,beta-unsaturated monocarboxylic acid	metabolite
bisphenol a 4,4'-isopropylidene diphenol: stimulates proliferative responses and cytokine productions of murine spleen cells and thymus cells in vitro. bisphenol : By usage, the methylenediphenols, HOC6H4CH2C6H4OH, commonly p,p-methylenediphenol, and their substitution products (generally derived from condensation of two equivalent amounts of a phenol with an aldehyde or ketone). The term also includes analogues in the the methylene (or substituted methylene) group has been replaced by a heteroatom.. bisphenol A : A bisphenol that is 4,4'-methanediyldiphenol in which the methylene hydrogens are replaced by two methyl groups.	3.35	5	0	bisphenol	endocrine disruptor; environmental contaminant; xenobiotic; xenoestrogen
cumene hydroperoxide cumene hydroperoxide: RN given refers to parent cpd. cumene hydroperoxide : A peroxol that is cumene in which the alpha-hydrogen is replaced by a hydroperoxy group.	2.73	3	0	peroxol	environmental contaminant; Mycoplasma genitalium metabolite; oxidising agent
terpin terpene : A hydrocarbon of biological origin having carbon skeleton formally derived from isoprene [CH2=C(CH3)CH=CH2].	2.05	1	0	p-menthane monoterpenoid
1,4-dihydroxyanthraquinone 1,4-dihydroxyanthraquinone: structure given in first source. quinizarin : A dihydroxyanthraquinone having the two hydroxy substituents at the 1- and 4-positions; formally derived from anthraquinone by replacement of two hydrogen atoms by hydroxy groups	3.1	1	0	dihydroxyanthraquinone	dye
cyclizine Cyclizine: A histamine H1 antagonist given by mouth or parenterally for the control of postoperative and drug-induced vomiting and in motion sickness. (From Martindale, The Extra Pharmacopoeia, 30th ed, p935). cyclizine : An N-alkylpiperazine in which one nitrogen of the piperazine ring is substituted by a methyl group, while the other is substituted by a diphenylmethyl group.	3.1	1	0	N-alkylpiperazine	antiemetic; central nervous system depressant; cholinergic antagonist; H1-receptor antagonist; local anaesthetic
bis(p-chlorophenyl)acetic acid bis(p-chlorophenyl)acetic acid: a metabolite of DDT; RN given refers to parent cpd.. bis(4-chlorophenyl)acetic acid : A organochlorine compound comprising acetic acid having two 4-chlorophenyl substituents attached at the 2-position.	1.96	1	0	monocarboxylic acid; monochlorobenzenes
lawsone lawsone: a molluscacide from leaves of Lawsonia inermis L. topical sunscreening agent; structure; powdered leaves of Lawsonia inermis(Lythraceae) used as brown hair dye. lawsone : 1,4-Naphthoquinone carrying a hydroxy function at C-2. It is obtained from the leaves of Lawsonia inermis.	2.05	1	0
rotenone Derris: A plant genus of the family FABACEAE. The root is a source of rotenoids (ROTENONE) and flavonoids. Some species of Pongamia have been reclassified to this genus and some to MILLETTIA. Some species of Deguelia have been reclassified to this genus.. rotenoid : Members of the class of tetrahydrochromenochromene that consists of a cis-fused tetrahydrochromeno[3,4-b]chromene skeleton and its substituted derivatives. The term was originally restricted to natural products, but is now also used to describe semi-synthetic and fully synthetic compounds.	7.59	2	0	organic heteropentacyclic compound; rotenones	antineoplastic agent; metabolite; mitochondrial NADH:ubiquinone reductase inhibitor; phytogenic insecticide; piscicide; toxin
2,6-dihydroxyanthraquinone 2,6-dihydroxyanthraquinone: structure given in first source. anthraflavic acid : A dihydroxyanthraquinone that is anthracene substituted by hydroxy groups at C-3 and C-7 and oxo groups at C-9 and C-10.	3.1	1	0	dihydroxyanthraquinone	antimutagen; plant metabolite
9,10-anthraquinone 9,10-anthraquinone : An anthraquinone that is anthracene in which positions 9 and 10 have been oxidised to carbonyls.	3.1	1	0	anthraquinone
diquat Diquat: A contact herbicide used also to produce desiccation and defoliation. (From Merck Index, 11th ed). diquat : The organic cation formed formally by addition of an ethylene bridge between the nitrogen atoms of 2,2'-bipyridine. Most often available as the dibromide.	2.15	1	0	organic cation	defoliant; herbicide
pyocyanine Pyocyanine: Antibiotic pigment produced by Pseudomonas aeruginosa.. pyocyanine : An iminium betaine that is 5-methylphenazin-5-ium which is substituted at position 1 by an oxidanidyl group. An antibiotic pigment produced by Pseudomonas aeruginosa.	2.21	1	0	iminium betaine; phenazines	antibacterial agent; bacterial metabolite; biological pigment; virulence factor
brompheniramine Brompheniramine: Histamine H1 antagonist used in treatment of allergies, rhinitis, and urticaria.. brompheniramine : Pheniramine in which the hydrogen at position 4 of the phenyl substituent is substituted by bromine. A histamine H1 receptor antagonist, brompheniramine is used (commonly as its maleate salt) for the symptomatic relief of allergic conditions, including rhinitis and conjunctivitis.	2.1	1	0	organobromine compound; pyridines	anti-allergic agent; H1-receptor antagonist
penicillin v Penicillin V: A broad-spectrum penicillin antibiotic used orally in the treatment of mild to moderate infections by susceptible gram-positive organisms.. phenoxymethylpenicillin : A penicillin compound having a 6beta-(phenoxyacetyl)amino side-chain.	2.1	1	0	penicillin allergen; penicillin
gramine gramine : An aminoalkylindole that is indole carrying a dimethylaminomethyl substituent at postion 3.	7.53	2	0	aminoalkylindole; indole alkaloid; tertiary amino compound	antibacterial agent; antiviral agent; plant metabolite; serotonergic antagonist
2,4,6-trichlorophenol [no description available]	2.02	1	0	trichlorophenol	carcinogenic agent
n-vinyl-2-pyrrolidinone N-vinyl-2-pyrrolidinone: monomer of POVIDONE; structure given in first source	2.78	3	0	pyrrolidin-2-ones
picric acid picric acid: used as antiseptic, astringent & stimulant for epitheliazation; structure. picric acid : A C-nitro compound comprising phenol having three nitro substtituents at the 2-, 4- and 6-positions.	2.06	1	0	C-nitro compound	antiseptic drug; explosive; fixative
thymol Thymol: A phenol obtained from thyme oil or other volatile oils used as a stabilizer in pharmaceutical preparations, and as an antiseptic (antibacterial or antifungal) agent.. thymol : A phenol that is a natural monoterpene derivative of cymene.	5.25	9	0	monoterpenoid; phenols	volatile oil component
salicylaldehyde o-hydroxybenzaldehyde: structure in first source	2.49	2	0	hydroxybenzaldehyde	nematicide; plant metabolite
1-naphthol 1-naphthol: RN given refers to parent cpd. 1-naphthol : A naphthol carrying a hydroxy group at position 1.. hydroxynaphthalene : Any member of the class of naphthalenes that is naphthalene carrying one or more hydroxy groups.	3.1	1	0	naphthol	genotoxin; human xenobiotic metabolite
2-aminodiphenyl aminobiphenyl : Any member of the class of biphenyls in which the biphenyl skeleton is substituted by at least one amino group.	3.1	1	0
2-phenylphenol 2-phenylphenol: RN given refers to parent cpd; structure. biphenyl-2-ol : A member of the class of hydroxybiphenyls that is biphenyl substituted by a hydroxy group at position 2. It is generally used as a post-harvest fungicide for citrus fruits.	3.1	1	0	hydroxybiphenyls	antifungal agrochemical; environmental food contaminant
xanthone xanthone : The parent compound of the xanthone class consisting of xanthene bearing a single oxo substituent at position 9.	7.11	1	0	xanthones	insecticide
quinoxalines quinoxaline : A naphthyridine in which the nitrogens are at positions 1 and 4.	3.12	5	0	mancude organic heterobicyclic parent; naphthyridine; ortho-fused heteroarene
quinoline [no description available]	3.1	1	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinolines
2-naphthylamine 2-Naphthylamine: A naphthalene derivative with carcinogenic action.. 2-naphthylamine : A naphthylamine carrying the amino group at position 2.	3.1	1	0	naphthylamine	carcinogenic agent
diphenyl diphenyl: RN given refers to unlabeled cpd; structure	2.91	3	0	aromatic fungicide; benzenes; biphenyls	antifungal agrochemical; antimicrobial food preservative
phenylpiperazine phenylpiperazine: RN given refers to parent cpd	2.1	1	0
4-biphenylamine 4-biphenylamine: used in detection of sulfates, & as a carcinogen in cancer research; RN given refers to parent cpd; structure. biphenyl-4-amine : An aminobiphenyl that is biphenyl substituted by an amino group at position 4.	3.1	1	0	aminobiphenyl	carcinogenic agent
4-phenylphenol 4-phenylphenol: RN given refers to cpd without isomeric designation. biphenyl-4-ol : A member of the class of hydroxybiphenyls that is biphenyl carrying a hydroxy group at position 4.	3.52	2	0	hydroxybiphenyls
xanthenes Xanthenes: Compounds with three aromatic rings in linear arrangement with an OXYGEN in the center ring.	2.91	4	0	xanthene
benzidine benzidine: RN given refers to parent cpd. benzidine : A member of the class of biphenyls that is 1,1'-biphenyl in which the hydrogen at the para-position of each phenyl group has been replaced by an amino group.	3.8	3	0	biphenyls; substituted aniline	carcinogenic agent
4,4'-dihydroxybiphenyl biphenyl-4,4'-diol : A member of the class of hydroxybiphenyls that is biphenyl with hydroxy groups at positions 4 and 4'.	3.1	1	0	hydroxybiphenyls
veratryl alcohol (3,4-dimethoxyphenyl)methanol : A member of the class of benzyl alcohols that is benzyl alcohol in which the hydrogens at positions 3 and 4 of the phenyl group are substituted by methoxy groups.	2.06	1	0	benzyl alcohols; dimethoxybenzene; primary alcohol	fungal metabolite
n,n-diethyl 4-phenylenediamine N,N-diethyl 4-phenylenediamine: RN given refers to parent cpd	2.03	1	0
veratric acid veratric acid: RN given refers to parent cpd; structure. 3,4-dimethoxybenzoic acid : A member of the class of benzoic acids that is benzoic acid substituted by methoxy groups at positions 2 and 3.	2.44	2	0	benzoic acids	allergen; plant metabolite
2-naphthoic acid 2-naphthoic acid: RN given refers to parent cpd. 2-naphthoic acid : A naphthoic acid that is naphthalene carrying a carboxy group at position 2.	2.49	2	0	naphthoic acid	mouse metabolite; xenobiotic metabolite
mecoprop mecoprop: RN given refers to cpd without isomeric designation; structure. 2-(4-chloro-2-methylphenoxy)propanoic acid : A monocarboxylic acid that is lactic acid in which the hydroxyl hydrogen is replaced by a 4-chloro-2-methylphenyl group.. mecoprop : A racemate comprising equimolar amounts of (R)- and (S)-mecoprop.	2.1	1	0	aromatic ether; monocarboxylic acid; monochlorobenzenes
synephrine [no description available]	2.1	1	0	ethanolamines; phenethylamine alkaloid; phenols	alpha-adrenergic agonist; plant metabolite
propylparaben Parabens: Methyl, propyl, butyl, and ethyl esters of p-hydroxybenzoic acid. They have been approved by the FDA as antimicrobial agents for foods and pharmaceuticals. (From Hawley's Condensed Chemical Dictionary, 11th ed, p872)	7.43	36	1	benzoate ester; paraben; phenols	antifungal agent; antimicrobial agent
benzoyl peroxide Benzoyl Peroxide: A peroxide derivative that has been used topically for BURNS and as a dermatologic agent in the treatment of ACNE and POISON IVY DERMATITIS. It is used also as a bleach in the food industry.	9.02	2	1	carbonyl compound
2,4-dihydroxybenzaldehyde 2,4-dihydroxybenzaldehyde : A dihydroxybenzaldehyde that is resorcinol which has been substituted by a formyl group para to one of the hydroxy groups.	2.1	1	0	dihydroxybenzaldehyde
1,2-diaminobenzene 1,2-diaminobenzene: RN given refers to parent cpd. 1,2-phenylenediamine : A phenylenediamine in which the two amino groups are ortho to each other.	2.11	1	0	phenylenediamine	hydrogen donor
4-butyrolactone 4-Butyrolactone: One of the FURANS with a carbonyl thereby forming a cyclic lactone. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent.. tetrahydrofuranone : Any oxolane having an oxo- substituent at any position on the tetrahydrofuran ring.. gamma-butyrolactone : A butan-4-olide that is tetrahydrofuran substituted by an oxo group at position 2.	2.76	3	0	butan-4-olide	metabolite; neurotoxin
ethyl lactate ethyl lactate: RN given refers to cpd with unspecified isomeric designation. ethyl 2-hydroxypropanoate : The ethyl ester obtained of 2-hydroxypropanoic acid.	2.72	2	0	ethyl ester; lactate ester; secondary alcohol	metabolite
furfuryl alcohol furfuryl alcohol: structure. furfuryl alcohol : A furan bearing a hydroxymethyl substituent at the 2-position.	2.07	1	0	furans; primary alcohol	Maillard reaction product
furaldehyde Furaldehyde: A heterocyclic compound consisting of a furan where the hydrogen at position 2 is substituted by a formyl group.. furfural : An aldehyde that is furan with the hydrogen at position 2 substituted by a formyl group.	4.09	14	0	aldehyde; furans	Maillard reaction product; metabolite
butylphen butylphen: irritant; structure. 4-tert-butylphenol : A member of the class of phenols that is phenol substituted with a tert-butyl group at position 4.	3.1	1	0	phenols	allergen
3-hydroxybenzoic acid 3-hydroxybenzoic acid: RN given refers to parent cpd. 3-hydroxybenzoic acid : A monohydroxybenzoic acid that is benzoic acid substituted by a hydroxy group at position 3. It has been isolated from Taxus baccata. It is used as an intermediate in the synthesis of plasticisers, resins, pharmaceuticals, etc.	3.11	5	0	monohydroxybenzoic acid	bacterial metabolite; plant metabolite
alpha-resorcylic acid alpha-resorcylic acid: RN given refers to parent cpd. 3,5-dihydroxybenzoic acid : A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 5.	3.28	6	0	dihydroxybenzoic acid; resorcinols	metabolite
trehalose alpha,alpha-trehalose : A trehalose in which both glucose residues have alpha-configuration at the anomeric carbon.	2.13	1	0	trehalose	Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
methyl gallate methyl gallate: has both immunosuppressive and phytogenic antineoplastic activities; isolated from Acer saccharinum. methyl 3,4,5-trihydroxybenzoate : A gallate ester obtained by the formal condensation of gallic acid with methanol. It exhibits anti-oxidant, anti-tumor, anti-microbial and anti-inflammatory properties.	7.44	143	0	gallate ester	anti-inflammatory agent; antioxidant; plant metabolite
methylparaben methylparaben: used as a preservative in cosmetics but potentiates UV-induced damage of skin; RN given refers to parent cpd. methylparaben : A 4-hydroxybenzoate ester resulting from the formal condensation of the carboxy group of 4-hydroxybenzoic acid with methanol. It is the most frequently used antimicrobial preservative in cosmetics. It occurs naturally in several fruits, particularly in blueberries.	4.02	4	0	paraben	antifungal agent; antimicrobial food preservative; neuroprotective agent; plant metabolite
alpha phellandrene alpha phellandrene: can be irritating to, & absorbed by the skin; ingestion can cause vomiting, diarrhea; RN given refers to cpd without isomeric designation; structure. alpha-phellandrene : One of a pair of phellandrene cyclic monoterpene double-bond isomers in which both double bonds are endocyclic (cf. alpha-phellandrene, where one of them is exocyclic).	2.25	1	0	cyclohexadiene; phellandrene	antimicrobial agent; plant metabolite; volatile oil component
gamma-terpinene gamma-terpinene: RN given refers to gamma-terpinene; structure. gamma-terpinene : One of three isomeric monoterpenes differing in the positions of their two double bonds (alpha- and beta-terpinene being the others). In gamma-terpinene the double bonds are at the 1- and 4-positions of the p-menthane skeleton.	2.72	2	0	cyclohexadiene; monoterpene	antioxidant; human xenobiotic metabolite; plant metabolite; volatile oil component
4-cymene 4-cymene: structure. p-cymene : A monoterpene that is toluene substituted by an isopropyl group at position 4.	2.52	2	0	monoterpene; toluenes	human urinary metabolite; plant metabolite; volatile oil component
4-isopropylphenol [no description available]	3.1	1	0	phenols	flavouring agent
4-hydroxyacetophenone 4-hydroxyacetophenone: promotes secretion of bile & bile salts, which promotes griseofulvin absorption in the duodenum. 4'-hydroxyacetophenone : A monohydroxyacetophenone carrying a hydroxy substituent at position 4'.	3.1	1	0	monohydroxyacetophenone	fungal metabolite; mouse metabolite; plant metabolite
4-anisic acid 4-methoxybenzoic acid: structure in first source. 4-methoxybenzoic acid : A methoxybenzoic acid substituted with a methoxy group at position C-4.	2.41	2	0	methoxybenzoic acid	plant metabolite
ethylbenzene [no description available]	2.03	1	0	alkylbenzene
styrene Styrene: A colorless, toxic liquid with a strong aromatic odor. It is used to make rubbers, polymers and copolymers, and polystyrene plastics.. styrene : A vinylarene that is benzene carrying a vinyl group. It has been isolated from the benzoin resin produced by Styrax species.	2.51	2	0	styrenes; vinylarene; volatile organic compound	mouse metabolite; mutagen; plant metabolite
nicotinyl alcohol Nicotinyl Alcohol: Alcohol analog of NICOTINIC ACID which is a direct-acting peripheral vasodilator that causes flushing and may decrease blood pressure. It is used in vasospasm and threatened GANGRENE.. 3-pyridinemethanol : A member of the class of pyridines that is pyridine which is substituted by a hydroxymethyl group at position 3 .	1.95	1	0	aromatic primary alcohol; pyridines	antilipemic drug; vasodilator agent
anisole anisole : A monomethoxybenzene that is benzene substituted by a methoxy group.	2.44	2	0	monomethoxybenzene	plant metabolite
quinuclidines Quinuclidines: A class of organic compounds which contain two rings that share a pair of bridgehead carbon atoms and contains an amine group.	2.01	1	0	quinuclidines; saturated organic heterobicyclic parent
4-benzylphenol 4-benzylphenol: metabolite of diphenylmethane; RN given refers to parent cpd	3.52	2	0
diphenylmethane diphenylmethane : A diarylmethane that is methane substituted by two phenyl groups.	2.07	1	0	diarylmethane
boric acid [no description available]	7.51	2	0	boric acids	astringent
1,2-dihydrostilbene 1,2-dihydrostilbene: intermdiate in biosynthesis of dihydrophenanthrenes from phenylalanine. 1,2-dihydrostilbene : A diphenylethane that is the 1,2-dihydro derivative of stilbene.	2	1	0	diphenylethane
2-ethylhexanol [no description available]	3.1	1	0	primary alcohol	plant metabolite; volatile oil component
4-anisidine 4-anisidine: RN given refers to parent cpd. p-anisidine : A substituted aniline that is aniline in which the hydrogen para to the amino group has been replaced by a methoxy group. It is used as a reagent for the detection of oxidation products such as aldehydes and ketones in fats and oils.	2.15	1	0	methoxybenzenes; primary amino compound; substituted aniline	genotoxin; reagent
4-phenylenediamine 4-phenylenediamine: agent hair dye responsible for contact dermatitis; RN given refers to parent cpd. 1,4-phenylenediamine : A phenylenediamine in which the amino functions are at positions 1 and 4 of the benzene nucleus.	3.97	2	1	phenylenediamine	allergen; dye; hapten; reagent
2,5-dioxopiperazine piperazine-2,5-dione : A cyclic peptide that is piperazine in which the hydrogens at positions 2 and 5 are replaced by oxo groups.	2.31	1	0	2,5-diketopiperazines; cyclic peptide
epichlorohydrin Epichlorohydrin: A chlorinated epoxy compound used as an industrial solvent. It is a strong skin irritant and carcinogen.. epichlorohydrin : An epoxide that is 1,2-epoxypropene in which one of the methyl hydrogens is substituted by chlorine.	2.13	1	0	epoxide; organochlorine compound
acrolein [no description available]	3.6	8	0	enal	herbicide; human xenobiotic metabolite; toxin
allylamine Allylamine: Possesses an unusual and selective cytotoxicity for VASCULAR SMOOTH MUSCLE cells in dogs and rats. Useful for experiments dealing with arterial injury, myocardial fibrosis or cardiac decompensation.	7.49	2	0	alkylamine
glyoxal [no description available]	2.8	3	0	dialdehyde	agrochemical; allergen; pesticide; plant growth regulator
2-methylpentane Hexanes: Six-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Various polyneuropathies are caused by hexane poisoning.	3.05	4	0	alkane
deanol Deanol: An antidepressive agent that has also been used in the treatment of movement disorders. The mechanism of action is not well understood.. N,N-dimethylethanolamine : A tertiary amine that is ethanolamine having two N-methyl substituents.	2.1	1	0	ethanolamines; tertiary amine	curing agent; radical scavenger
acetic anhydride acetic anhydride: RN given refers to unlabeled cpd; structure. acetic anhydride : An acyclic carboxylic anhydride derived from acetic acid.	2.6	1	0	acyclic carboxylic anhydride	metabolite; reagent
melamine melamine: RN given refers to parent cpd; structure. melamine : A trimer of cyanamide, with a 1,3,5-triazine skeleton.	7.11	1	0	triamino-1,3,5-triazine	xenobiotic metabolite
bromobenzene [no description available]	2.02	1	0	bromoarene; bromobenzenes; volatile organic compound	hepatotoxic agent; mouse metabolite; non-polar solvent
cyclohexanol Cyclohexanols: Monohydroxy derivatives of cyclohexanes that contain the general formula R-C6H11O. They have a camphorlike odor and are used in making soaps, insecticides, germicides, dry cleaning, and plasticizers.. cyclohexanols : An alcohol in which one or more hydroxy groups are attached to a cyclohexane skeleton.	2.99	4	0	cyclohexanols; secondary alcohol	solvent
thiophenol thiophenol : A thiol in which the sulfanyl group is attached to a phenyl group.	2	1	0	aryl thiol
4-methylmorpholine [no description available]	2.1	1	0
n-butylamine n-butylamine: RN given refers to parent cpd. butan-1-amine : A primary aliphatic amine that is butane substituted by an amino group at position 1.	2.1	1	0	primary aliphatic amine
pyrroles 1H-pyrrole : A tautomer of pyrrole that has the double bonds at positions 2 and 4.. pyrrole : A five-membered monocyclic heteroarene comprising one NH and four CH units which forms the parent compound of the pyrrole group of compounds. Its five-membered ring structure has three tautomers. A 'closed class'.. azole : Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen.	3.55	8	0	pyrrole; secondary amine
thiophenes Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.	2.69	3	0	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
isopropyl myristate isopropyl myristate: used for microemulsions; structure	2.17	1	0	fatty acid ester
n-hexane hexane : An unbranched alkane containing six carbon atoms.	2.63	2	0	alkane; volatile organic compound	neurotoxin; non-polar solvent
piperidine [no description available]	2.1	1	0	azacycloalkane; piperidines; saturated organic heteromonocyclic parent; secondary amine	base; catalyst; human metabolite; non-polar solvent; plant metabolite; protic solvent; reagent
morpholine [no description available]	2.1	1	0	morpholines; saturated organic heteromonocyclic parent	NMR chemical shift reference compound
1-hexanol 1-hexanol: RN given refers to parent cpd. hexanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of six carbon atoms.. hexan-1-ol : A primary alcohol that is hexane substituted by a hydroxy group at position 1.	2.01	1	0	hexanol; primary alcohol	alarm pheromone; antibacterial agent; fragrance; plant metabolite
hexahydroazepine hexahydroazepine: RN given refers to parent cpd. azepane : An azacycloalkane that is cycloheptane in which one of the carbon atoms is replaced by a nitrogen atom.	2.1	1	0	azacycloalkane; azepanes; saturated organic heteromonocyclic parent
heptanol Heptanol: A colorless liquid with a fragrant odor. It is used as an intermediate, solvent and in cosmetics.. heptanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of seven carbon atoms.. heptan-1-ol : A primary alcohol that is heptane substituted by a hydroxy group at position 1. It has been isolated from Capillipedium parviflorum.	2.01	1	0	heptanol; primary alcohol	flavouring agent; fragrance; gap junctional intercellular communication inhibitor; plant metabolite
pelargonic acid pelargonic acid: K salt acts as cariostatic agent; RN given refers to parent cpd; structure. nonanoic acid : A C9 straight-chain saturated fatty acid which occurs naturally as esters of the oil of pelargonium. Has antifungal properties, and is also used as a herbicide as well as in the preparation of plasticisers and lacquers.	2.82	3	0	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; antifeedant; Daphnia magna metabolite; plant metabolite
triethylene glycol triethylene glycol : A poly(ethylene glycol) that is octane-1,8-diol in which the carbon atoms at positions 3 and 6 have been replaced by oxygen atoms.	9.79	9	0	diol; poly(ethylene glycol); primary alcohol	plasticiser
n-decyl alcohol n-decyl alcohol: RN given refers to parent cpd. decanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of ten carbon atoms.. decan-1-ol : A fatty alcohol consisting of a hydroxy function at C-1 of an unbranched saturated chain of ten carbon atoms.	2.01	1	0	decanol; primary alcohol	metabolite; pheromone; protic solvent
undecan-1-ol undecan-1-ol : A primary alcohol that is undecane substituted by a hydroxy group at position 1.. undecanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of eleven carbon atoms.	2.01	1	0	primary alcohol; undecanol	flavouring agent; plant metabolite
dodecanol Dodecanol: A saturated 12-carbon fatty alcohol obtained from coconut oil fatty acids. It has a floral odor and is used in detergents, lubricating oils, and pharmaceuticals. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). dodecanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of twelve carbon atoms.. dodecan-1-ol : A primary alcohol that is dodecane in which a hydrogen from one of the methyl groups is replaced by a hydroxy group. It is registered for use in apple and pear orchards as a Lepidopteran pheromone/sex attractant, used to disrupt the mating behaviour of certain moths whose larvae destroy crops.	2.01	1	0	dodecanol; primary alcohol	bacterial metabolite; cosmetic; insect attractant; insecticide; pheromone; plant metabolite
1-tridecanol 1-tridecanol: RN given refers to parent cpd. tridecan-1-ol : A long-chain primary fatty alcohol that is tridecane substituted by a hydroxy group at position 1.. tridecanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of thirteen carbon atoms.	2.01	1	0	long-chain primary fatty alcohol; tridecanol	bacterial metabolite; human metabolite; plant metabolite
behenic acid behenic acid: RN given refers to parent cpd; structure. docosanoic acid : A straight-chain, C22, long-chain saturated fatty acid.	2.46	2	0	long-chain fatty acid; straight-chain saturated fatty acid	plant metabolite
stearyl alcohol octadecan-1-ol : A long-chain primary fatty alcohol consisting of a hydroxy function at C-1 of an unbranched saturated chain of 18 carbon atoms.. octadecanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of eighteen carbon atoms.	1.99	1	0	long-chain primary fatty alcohol; octadecanol	algal metabolite; human metabolite; plant metabolite
ergotamine Ergotamine: A vasoconstrictor found in ergot of Central Europe. It is a serotonin agonist that has been used as an oxytocic agent and in the treatment of MIGRAINE DISORDERS.. ergotamine : A peptide ergot alkaloid that is dihydroergotamine in which a double bond replaces the single bond between positions 9 and 10.	2.1	1	0	peptide ergot alkaloid	alpha-adrenergic agonist; mycotoxin; non-narcotic analgesic; oxytocic; serotonergic agonist; vasoconstrictor agent
obidoxime chloride Obidoxime Chloride: Cholinesterase reactivator occurring in two interchangeable isomeric forms, syn and anti.	1.98	1	0
propylene propylene: structure	2.6	1	0	alkene; gas molecular entity	refrigerant; xenobiotic
2,2,2-trichloroethanol [no description available]	3.1	1	0	chloroethanol	mouse metabolite
anthrarufin 1,5-dihydroxyanthraquinone: used in ferric ion sensing as an inclusion complex with beta-cyclodextrin; structure in first source. anthrarufin : A dihydroxyanthraquinone that is anthracene-9,10-dione substituted by hydroxy groups at positions 1 and 5.	3.1	1	0	dihydroxyanthraquinone
3,4,5-trimethoxybenzoic acid 3,4,5-trimethoxybenzoic acid: RN given refers to parent cpd; structure. 3,4,5-trimethoxybenzoic acid : A benzoic acid derivative carrying 3-, 4- and 5-methoxy substituents.	4.69	29	0	benzoic acids; methoxybenzenes	human urinary metabolite; human xenobiotic metabolite; plant metabolite
maltol maltol: found in bark of young larch trees; isolated from Passiflora incarnata; possesses depressant properties in mice; potentiates hexobarbital-induced narcosis & inhibits spontaneous motor activity; structure	2.05	1	0	4-pyranones	metabolite
2-toluic acid 2-toluic acid: RN given refers to parent cpd; structure. o-toluic acid : A methylbenzoic acid that is benzoic acid substituted by a methyl group at position 2.	3.1	1	0	methylbenzoic acid	xenobiotic metabolite
2'-hydroxyacetophenone 2-acetylphenol : A monohydroxyacetophenone that is acetophenone in which one of the hydrogens ortho to the acetyl group has been replaced by a hydroxy group.	2.1	1	0	monohydroxyacetophenone; phenols	flavouring agent
framycetin Framycetin: A component of NEOMYCIN that is produced by Streptomyces fradiae. On hydrolysis it yields neamine and neobiosamine B. (From Merck Index, 11th ed). framycetin : A tetracyclic antibacterial agent derived from neomycin, being a glycoside ester of neamine and neobiosamine B.	3.77	11	0	aminoglycoside	allergen; antibacterial drug; Escherichia coli metabolite
scoparone scoparone: structure. scoparone : A member of the class of coumarins that is esculetin in which the two hydroxy groups at positions 6 and 7 are replaced by methoxy groups. It is a major constituent of the Chinese herbal medicine Yin Chen Hao, and exhibits a variety of pharmacological activities such as anti-inflammatory, anti-allergic, and anti-tumor activities.	2.05	1	0	aromatic ether; coumarins	anti-allergic agent; anti-inflammatory agent; antihypertensive agent; antilipemic drug; immunosuppressive agent; plant metabolite
ethyl-p-hydroxybenzoate ethyl-p-hydroxybenzoate: structure	3.1	1	0	ethyl ester; paraben	antifungal agent; antimicrobial food preservative; phytoestrogen; plant metabolite
piperonal piperonal: has been used as a pediculicide; structure. piperonal : An arenecarbaldehyde that is 1,3-benzodioxole substituted by a formyl substituent at position 5. It has been isolated from Piper nigrum.	2.1	1	0	arenecarbaldehyde; benzodioxoles	fragrance; insect repellent; plant metabolite
n-methylpyrrolidine N-methylpyrrolidine: RN given refers to parent cpd	2.1	1	0
3-tert-butyl-4-hydroxyanisole 3-tert-butyl-4-hydroxyanisole : An aromatic ether that is 4-methoxyphenol in which one of the hydrogens ortho- to the phenolic hydroxy group is replaced by a tert-butyl group.	3.54	2	0	aromatic ether; phenols	antioxidant; human xenobiotic metabolite
vanillic acid Vanillic Acid: A flavoring agent. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13).. vanillic acid : A monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3.	13.49	103	1	methoxybenzoic acid; monohydroxybenzoic acid	plant metabolite
triethylamine [no description available]	2.1	1	0	tertiary amine
pyrazolanthrone pyrazolanthrone: JNK (c-Jun N-terminal kinase) inhibitor; structure in first source. anthra[1,9-cd]pyrazol-6(2H)-one : A member of the class of anthrapyrazoles that is anthra[1,9-cd]pyrazole substituted at position 6 by an oxo group. An inhibitor of c-Jun N-terminal kinase.	2.05	1	0	anthrapyrazole; aromatic ketone; cyclic ketone	antineoplastic agent; c-Jun N-terminal kinase inhibitor; geroprotector
meglumine Meglumine: 1-Deoxy-1-(methylamino)-D-glucitol. A derivative of sorbitol in which the hydroxyl group in position 1 is replaced by a methylamino group. Often used in conjunction with iodinated organic compounds as contrast medium.. N-methylglucamine : A hexosamine that is D-glucitol in which the hydroxy group at position 1 is substituted by the nitrogen of a methylamino group. A crystalline base, it is used in preparing salts of certain acids for use as diagnostic radiopaque media, while its antimonate is used as an antiprotozoal in the treatment of leishmaniasis.	2.42	2	0	hexosamine; secondary amino compound
chloroprocaine chloroprocaine: RN given refers to parent cpd; structure. chloroprocaine : Procaine in which one of the hydrogens ortho- to the carboxylic acid group is substituted by chlorine. It is used as its monohydrochloride salt as a local anaesthetic, particularly for oral surgery. It has the advantage over lidocaine of constricting blood vessels, so reducing bleeding.	2.1	1	0	benzoate ester; monochlorobenzenes	central nervous system depressant; local anaesthetic; peripheral nervous system drug
uridine diphosphate glucose Uridine Diphosphate Glucose: A key intermediate in carbohydrate metabolism. Serves as a precursor of glycogen, can be metabolized into UDPgalactose and UDPglucuronic acid which can then be incorporated into polysaccharides as galactose and glucuronic acid. Also serves as a precursor of sucrose lipopolysaccharides, and glycosphingolipids.. UDP-alpha-D-glucose : The alpha-anomer of UDP-alpha-D-glucose. It is used in nucleotide sugars metabolism.	2.04	1	0	UDP-D-glucose	fundamental metabolite
1-naphthylamine 1-Naphthylamine: A suspected industrial carcinogen (and listed as such by OSHA). Its N-hydroxy metabolite is strongly carcinogenic and mutagenic.. naphthylamine : A primary arylamine that is naphthalene substituted by an amino group at unspecified position.. 1-naphthylamine : A naphthylamine that is naphthalene substituted by an amino group at position 1.	3.1	1	0	naphthylamine	human xenobiotic metabolite
syringaldehyde syringaldehyde: isolated from nonfermented fiber fractions of oat hulls and cottonseed hulls. syringaldehyde : A hydroxybenzaldehyde that is 4-hydroxybenzaldehyde substituted by methoxy groups at positions 3 and 5. Isolated from Pisonia aculeata and Panax japonicus var. major, it exhibits hypoglycemic activity.	3.7	9	0	dimethoxybenzene; hydroxybenzaldehyde	hypoglycemic agent; plant metabolite
2-naphthol 2-naphthol: RN given refers to parent cpd. 2-naphthol : A naphthol carrying a hydroxy group at position 2.. naphthols : Any hydroxynaphthalene derivative that has a single hydroxy substituent.	4.26	3	0	naphthol	antinematodal drug; genotoxin; human urinary metabolite; human xenobiotic metabolite; mouse metabolite; radical scavenger
shikimic acid Shikimic Acid: A tri-hydroxy cyclohexene carboxylic acid important in biosynthesis of so many compounds that the shikimate pathway is named after it.. shikimic acid : A cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid substituted by hydroxy groups at positions 3, 4 and 5 (the 3R,4S,5R stereoisomer). It is an intermediate metabolite in plants and microorganisms.	10.05	13	0	alpha,beta-unsaturated monocarboxylic acid; cyclohexenecarboxylic acid; hydroxy monocarboxylic acid	Escherichia coli metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
nitrilotriacetic acid Nitrilotriacetic Acid: A derivative of acetic acid, N(CH2COOH)3. It is a complexing (sequestering) agent that forms stable complexes with Zn2+. (From Miall's Dictionary of Chemistry, 5th ed.)	2.03	1	0	NTA; tricarboxylic acid	carcinogenic agent; nephrotoxic agent
protocatechualdehyde protocatechualdehyde: found in wheat grains, wheat seedlings, & other plants; RN given refers to parent cpd; see also rancinamycins; structure	2.97	4	0	dihydroxybenzaldehyde
citronellol citronellol: alcohol form of citronellal; found in rose oil; RN given refers to parent cpd without isomeric designation; structure. citronellol : A monoterpenoid that is oct-6-ene substituted by a hydroxy group at position 1 and methyl groups at positions 3 and 7.. insect repellent : An insecticide that acts as a repellent to insects.	3.51	2	0	monoterpenoid	plant metabolite
ethyl acetate ethyl acetate : The acetate ester formed between acetic acid and ethanol.	4.33	17	0	acetate ester; ethyl ester; volatile organic compound	EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor; metabolite; polar aprotic solvent; Saccharomyces cerevisiae metabolite
hexanoic acid hexanoic acid : A C6, straight-chain saturated fatty acid.	4.08	4	0	medium-chain fatty acid; straight-chain saturated fatty acid	human metabolite; plant metabolite
n-heptane Heptanes: Seven-carbon alkanes with the formula C7H16.. heptane : A straight-chain alkane with seven carbon atoms. It has been found in Jeffrey pine (Pinus jeffreyi).	2	1	0	alkane; volatile organic compound	non-polar solvent; plant metabolite
1-nonanol nonanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of nine carbon atoms.. nonan-1-ol : A nonanol that is nonane substituted by a hydroxy group at position 1. It has been isolated as a component of volatile oils from plants like Hordeum vulgare.	2.01	1	0	nonanol; primary alcohol	antifungal agent; flavouring agent; plant metabolite; volatile oil component
sodium cyanide Sodium Cyanide: A highly poisonous compound that is an inhibitor of many metabolic processes and is used as a test reagent for the function of chemoreceptors. It is also used in many industrial processes.. sodium cyanide : A cyanide salt containing equal numbers of sodium cations and cyanide anions.	1.98	1	0	cyanide salt; one-carbon compound; sodium salt	EC 1.15.1.1 (superoxide dismutase) inhibitor
pregnenolone [no description available]	3.5	2	0	20-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; C21-steroid	human metabolite; mouse metabolite
yohimbine Yohimbine: A plant alkaloid with alpha-2-adrenergic blocking activity. Yohimbine has been used as a mydriatic and in the treatment of ERECTILE DYSFUNCTION.. yohimbine : An indole alkaloid with alpha2-adrenoceptor antagonist activity. It is produced by Corynanthe johimbe and Rauwolfia serpentina.	2.17	1	0	methyl 17-hydroxy-20xi-yohimban-16-carboxylate	alpha-adrenergic antagonist; dopamine receptor D2 antagonist; serotonergic antagonist
2-chloroadenosine 5-chloroformycin A: structure given in first source	2.38	2	0	purine nucleoside
ditiocarb Ditiocarb: A chelating agent that has been used to mobilize toxic metals from the tissues of humans and experimental animals. It is the main metabolite of DISULFIRAM.. diethyldithiocarbamic acid : A member of the class of dithiocarbamic acids that is diethylcarbamic acid in which both of the oxygens are replaced by sulfur.	3.1	1	0	dithiocarbamic acids	chelator; copper chelator
1,2-dihydroxybenzene-3,5-disulfonic acid disodium salt 1,2-Dihydroxybenzene-3,5-Disulfonic Acid Disodium Salt: A colorimetric reagent for iron, manganese, titanium, molybdenum, and complexes of zirconium. (From Merck Index, 11th ed)	1.97	1	0	organic molecular entity
dulcin dulcin: structure	2.02	1	0	ureas
mequinol mequinol: depigmenting agent; RN given refers to parent cpd	4.53	4	0	methoxybenzenes; phenols	metabolite
potassium cyanide [no description available]	2.38	2	0	cyanide salt; one-carbon compound; potassium salt	EC 1.15.1.1 (superoxide dismutase) inhibitor; EC 1.9.3.1 (cytochrome c oxidase) inhibitor; neurotoxin
aziridine [no description available]	2.1	1	0	azacycloalkane; aziridines; saturated organic heteromonocyclic parent	alkylating agent
catechin Catechin: An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.. catechin : Members of the class of hydroxyflavan that have a flavan-3-ol skeleton and its substituted derivatives.. rac-catechin : A racemate comprising equimolar amounts of (+)- and (-)-catechin. (+)-catechin : The (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite.	13.7	435	3	catechin	antioxidant; plant metabolite
phenetidine Phenetidine: Used in the manufacture of acetophenetidin.. 4-ethoxyaniline : An aromatic ether that is aniline in which the hydrogen at position 4 is replaced by an ethoxy group. It is a hydrolysis metabolite of phenacetin.	3.1	1	0	aromatic ether; primary amino compound; substituted aniline	drug metabolite
quinazolines Quinazolines: A group of aromatic heterocyclic compounds that contain a bicyclic structure with two fused six-membered aromatic rings, a benzene ring and a pyrimidine ring.. quinazoline : A mancude organic heterobicyclic parent that is naphthalene in which the carbon atoms at positions 1 and 3 have been replaced by nitrogen atoms.. quinazolines : Any organic heterobicyclic compound based on a quinazoline skeleton and its substituted derivatives.	2.74	3	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinazolines
acridines Acridines: Compounds that include the structure of acridine.. acridine : A polycyclic heteroarene that is anthracene in which one of the central CH groups is replaced by a nitrogen atom.	1.99	1	0	acridines; mancude organic heterotricyclic parent; polycyclic heteroarene	genotoxin
indazoles Indazoles: A group of heterocyclic aromatic organic compounds consisting of the fusion of BENZENE and PYRAZOLES.	2.01	1	0	indazole
azulene [no description available]	2.15	1	0	azulenes; mancude carbobicyclic parent; ortho-fused bicyclic arene	plant metabolite; volatile oil component
cyclopentane Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.	2.9	3	0	cycloalkane; cyclopentanes; volatile organic compound	non-polar solvent
isoxazoles Isoxazoles: Azoles with an OXYGEN and a NITROGEN next to each other at the 1,2 positions, in contrast to OXAZOLES that have nitrogens at the 1,3 positions.. isoxazole : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing three carbon atoms and an oxygen and nitrogen atom adjacent to each other. It is the parent of the class of isoxazoles.. isoxazoles : Oxazoles in which the N and O atoms are adjacent.	2.41	2	0	isoxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
oxazoles Oxazoles: Five-membered heterocyclic ring structures containing an oxygen in the 1-position and a nitrogen in the 3-position, in distinction from ISOXAZOLES where they are at the 1,2 positions.. 1,3-oxazole : A five-membered monocyclic heteroarene that is an analogue of cyclopentadiene with O in place of CH2 at position 1 and N in place of CH at position 3.. oxazole : An azole based on a five-membered heterocyclic aromatic skeleton containing one N and one O atom.	2.69	3	0	1,3-oxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
thiazoles [no description available]	4.13	15	0	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
pyrazines Pyrazines: A heterocyclic aromatic organic compound with the chemical formula C4H4N2.. pyrazine : A diazine that is benzene in which the carbon atoms at positions 1 and 4 have been replaced by nitrogen atoms.	2.41	1	0	diazine; pyrazines	Daphnia magna metabolite
nitroblue tetrazolium Nitroblue Tetrazolium: Colorless to yellow dye that is reducible to blue or black formazan crystals by certain cells; formerly used to distinguish between nonbacterial and bacterial diseases, the latter causing neutrophils to reduce the dye; used to confirm diagnosis of chronic granulomatous disease.	2.4	2	0	organic cation
ephedrine Ephedrine: A phenethylamine found in EPHEDRA SINICA. PSEUDOEPHEDRINE is an isomer. It is an alpha- and beta-adrenergic agonist that may also enhance release of norepinephrine. It has been used for asthma, heart failure, rhinitis, and urinary incontinence, and for its central nervous system stimulatory effects in the treatment of narcolepsy and depression. It has become less extensively used with the advent of more selective agonists.. (-)-ephedrine : A phenethylamine alkaloid that is 2-phenylethanamine substituted by a methyl group at the amino nitrogen and a methyl and a hydroxy group at position 2 and 1 respectively.	2.1	1	0	phenethylamine alkaloid; phenylethanolamines	bacterial metabolite; environmental contaminant; nasal decongestant; plant metabolite; sympathomimetic agent; vasoconstrictor agent; xenobiotic
diiodotyrosine Diiodotyrosine: A product from the iodination of MONOIODOTYROSINE. In the biosynthesis of thyroid hormones, diiodotyrosine residues are coupled with other monoiodotyrosine or diiodotyrosine residues to form T4 or T3 thyroid hormones (THYROXINE and TRIIODOTHYRONINE).. diiodotyrosine : A dihalogenated L-tyrosine which has two iodo-substituents on the benzyl moiety.. 3,5-diiodo-L-tyrosine : A diiodotyrosine that is L-tyrosine carrying iodo-substituents at positions C-3 and C-5 of the benzyl group. It is an intermediate in the thyroid hormone synthesis.	2.34	2	0	diiodotyrosine; L-tyrosine derivative; non-proteinogenic L-alpha-amino acid	human metabolite; mouse metabolite
muscarine Muscarine: A toxic alkaloid found in Amanita muscaria (fly fungus) and other fungi of the Inocybe species. It is the first parasympathomimetic substance ever studied and causes profound parasympathetic activation that may end in convulsions and death. The specific antidote is atropine.	2.38	2	0	monosaccharide
hydrazine diamine : Any polyamine that contains two amino groups.	3.5	8	0	azane; hydrazines	EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
gamma-resorcylic acid [no description available]	2.4	2	0	dihydroxybenzoic acid	metabolite
4-hydroxyphenyllactic acid 4-hydroxyphenyllactic acid: tyrosing metabolite; RN given refers to cpd without isomeric designation. 3-(4-hydroxyphenyl)lactic acid : A 2-hydroxy carboxylic acid that is lactic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group.	2.17	1	0	2-hydroxy carboxylic acid; phenols	bacterial metabolite; human metabolite
paraoxon [no description available]	2.03	1	0	aryl dialkyl phosphate; organophosphate insecticide	EC 3.1.1.7 (acetylcholinesterase) inhibitor; mouse metabolite
dibenzepin dibenzepin: was heading 1975-94 (see under DIBENZAZEPINES 1975-90); use DIBENZAZEPINES to search DIBENZEPIN 1975-94; tricyclic antidepressant similar in action to imipramine	2.1	1	0	dibenzodiazepine
galantamine Galantamine: A benzazepine derived from norbelladine. It is found in GALANTHUS and other AMARYLLIDACEAE. It is a cholinesterase inhibitor that has been used to reverse the muscular effects of GALLAMINE TRIETHIODIDE and TUBOCURARINE and has been studied as a treatment for ALZHEIMER DISEASE and other central nervous system disorders.. galanthamine : A benzazepine alkaloid isolated from certain species of daffodils.	2.59	2	0	benzazepine alkaloid fundamental parent; benzazepine alkaloid; organic heterotetracyclic compound; tertiary amino compound	antidote to curare poisoning; cholinergic drug; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; plant metabolite
methysergide Methysergide: An ergot derivative that is a congener of LYSERGIC ACID DIETHYLAMIDE. It antagonizes the effects of serotonin in blood vessels and gastrointestinal smooth muscle, but has few of the properties of other ergot alkaloids. Methysergide is used prophylactically in migraine and other vascular headaches and to antagonize serotonin in the carcinoid syndrome.. methysergide : A synthetic ergot alkaloid, structurally related to the oxytocic agent methylergonovine and to the potent hallucinogen LSD and used prophylactically to reduce the frequency and intensity of severe vascular headaches.	1.98	1	0	ergoline alkaloid
thymidine monophosphate Thymidine Monophosphate: 5-Thymidylic acid. A thymine nucleotide containing one phosphate group esterified to the deoxyribose moiety.. dTMP : The neutral species of thymidine 5'-monophosphate (2'-deoxythymidine 5'-monophosphate).	1.96	1	0	thymidine 5'-monophosphate	fundamental metabolite
cuprizone [no description available]	2.21	1	0	organonitrogen compound; organooxygen compound
methyl-4-tyramine methyl-4-tyramine: found in barley malt; RN given refers to parent cpd; structure given in first source	2.17	1	0	tyramines	mouse metabolite
trifluoroethylamine trifluoroethylamine: RN given refers to cpd with unspecified fluorine locants	2.1	1	0
4-hydroxyphenobarbital [no description available]	3.1	1	0	barbiturates
prenylamine Prenylamine: A drug formerly used in the treatment of angina pectoris but superseded by less hazardous drugs. Prenylamine depletes myocardial catecholamine stores and has some calcium channel blocking activity. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1406)	1.96	1	0	diarylmethane
lithocholic acid Lithocholic Acid: A bile acid formed from chenodeoxycholate by bacterial action, usually conjugated with glycine or taurine. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as cholagogue and choleretic.. lithocholic acid : A monohydroxy-5beta-cholanic acid with a alpha-hydroxy substituent at position 3. It is a bile acid obtained from chenodeoxycholic acid by bacterial action.. lithocholate : A bile acid anion that is the conjugate base of lithocholic acid.	3.1	1	0	bile acid; C24-steroid; monohydroxy-5beta-cholanic acid	geroprotector; human metabolite; mouse metabolite
xanthinol niacinate Xanthinol Niacinate: A vasodilator used in peripheral vascular disorders and insufficiency. It may cause gastric discomfort and hypotension.	1.95	1	0
thiazolidine-4-carboxylic acid thiazolidine-4-carboxylic acid: active against thimerosal intoxication; acts on cell membranes of tumor cells causing reverse transformation to normal cells; RN given refers to parent cpd	1.97	1	0	alpha-amino acid zwitterion; non-proteinogenic alpha-amino acid; sulfur-containing amino acid; thiazolidinemonocarboxylic acid	antidote; antioxidant; hepatoprotective agent
4-methylcatechol [no description available]	2.52	2	0	methylcatechol	antioxidant; carcinogenic agent; hapten; human metabolite; plant metabolite
2-fluoroethylamine 2-fluoroethylamine: structure in first source	2.1	1	0
fluorobenzenes Fluorobenzenes: Derivatives of BENZENE that contain FLUORINE.. monofluorobenzene : The simplest member of the class of monofluorobenzenes that is benzene carrying a single fluoro substituent.. fluorobenzenes : Any fluoroarene that is a benzene or a substituted benzene carrying at least one fluoro group.	2.08	1	0	monofluorobenzenes	NMR chemical shift reference compound
dextropropoxyphene Dextropropoxyphene: A narcotic analgesic structurally related to METHADONE. Only the dextro-isomer has an analgesic effect; the levo-isomer appears to exert an antitussive effect.. propoxyphene : A racemate of the (1R,2R)- and (1S,2R)- diastereoisomers.. dextropropoxyphene : The (1S,2R)-(+)-diastereoisomer of propoxyphene.	2.1	1	0	1-benzyl-3-(dimethylamino)-2-methyl-1-phenylpropyl propanoate	mu-opioid receptor agonist; opioid analgesic
mesoxalic acid mesoxalic acid: structure	2.05	1	0	oxo dicarboxylic acid
chenodeoxycholic acid Chenodeoxycholic Acid: A bile acid, usually conjugated with either glycine or taurine. It acts as a detergent to solubilize fats for intestinal absorption and is reabsorbed by the small intestine. It is used as cholagogue, a choleretic laxative, and to prevent or dissolve gallstones.. chenodeoxycholic acid : A dihydroxy-5beta-cholanic acid that is (5beta)-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 7 respectively.. chenodeoxycholate : Conjugate base of chenodeoxycholic acid; major species at pH 7.3.	3.1	1	0	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
naphthazarin naphthazarin: fish toxin; isolated for first time from the walnut onigurmi, Juglans mandshurica maxim var. Sieboldiana Makino; structure. naphthazarin : A naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 5 and 8 are replaced by hydroxy groups.	2.1	1	0	hydroxy-1,4-naphthoquinone	acaricide; antibacterial agent; antineoplastic agent; apoptosis inducer; geroprotector; plant metabolite
fusarium Fusarium: A mitosporic Hypocreales fungal genus, various species of which are important parasitic pathogens of plants and a variety of vertebrates. Teleomorphs include GIBBERELLA.	4.56	7	0
boldine [no description available]	2.31	1	0	aporphine alkaloid
rhein [no description available]	4.12	3	1	dihydroxyanthraquinone
epitestosterone Epitestosterone: The 17-alpha isomer of TESTOSTERONE, derived from PREGNENOLONE via the delta5-steroid pathway, and via 5-androstene-3-beta,17-alpha-diol. Epitestosterone acts as an antiandrogen in various target tissues. The ratio between testosterone/epitestosterone is used to monitor anabolic drug abuse.. epitestosterone : An androstanoid that is the C-17 epimer of testosterone.	3.1	1	0	17alpha-hydroxy steroid; 3-oxo-Delta(4) steroid; androstanoid	androgen antagonist; human metabolite
aloe emodin aloe emodin: structure distinct from emodin; this does not mean emodin from aloe. Aloe emodin : A dihydroxyanthraquinone that is chrysazin carrying a hydroxymethyl group at position 3. It has been isolated from plant species of the genus Aloe.	2.42	2	0	aromatic primary alcohol; dihydroxyanthraquinone	antineoplastic agent; plant metabolite
chrysophanic acid chrysophanic acid: RN given refers to parent cpd; structure in Merck, 9th ed, #2260. chrysophanol : A trihydroxyanthraquinone that is chrysazin with a methyl substituent at C-3. It has been isolated from Aloe vera and exhibits antiviral and anti-inflammatory activity.	4.22	5	0	dihydroxyanthraquinone	anti-inflammatory agent; antiviral agent; plant metabolite
imperatorin imperatorin: tumor necrosis factor antagonist; furanocoumarin from West African medicinal plant Clausena anisata; structure in Negwer, 5th ed, #3005. imperatorin : A member of the class of psoralens that is psoralen substituted by a prenyloxy group at position 8. Isolated from Angelica dahurica and Angelica koreana, it acts as a acetylcholinesterase inhibitor.	2.49	2	0	psoralens	EC 3.1.1.7 (acetylcholinesterase) inhibitor; metabolite
phosphoadenosine phosphosulfate Phosphoadenosine Phosphosulfate: 3'-Phosphoadenosine-5'-phosphosulfate. Key intermediate in the formation by living cells of sulfate esters of phenols, alcohols, steroids, sulfated polysaccharides, and simple esters, such as choline sulfate. It is formed from sulfate ion and ATP in a two-step process. This compound also is an important step in the process of sulfur fixation in plants and microorganisms.. 3'-phospho-5'-adenylyl sulfate : An adenosine bisphosphate having monophosphate groups at the 3'- and 5'-positions and a sulfo group attached to the phosphate at position 5'.	1.99	1	0	acyl sulfate; adenosine bisphosphate; purine ribonucleoside bisphosphate	Escherichia coli metabolite; mouse metabolite
flavanone flavanone: RN given refers to cpd with unspecified isomeric designation; structure in first source. flavanone : The simplest member of the class of flavanones that consists of flavan bearing an oxo substituent at position 4.	2.1	1	0	flavanones
salicylurate salicylurate: RN given refers to parent cpd. salicyluric acid : An N-acylglycine in which the acyl group is specified as 2-hydroxybenzoyl.. salicylurate : A monocarboxylic acid anion that is the conjugate base of salicyluric acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.	2.07	1	0	N-acylglycine; secondary carboxamide	human xenobiotic metabolite; uremic toxin
kainic acid Kainic Acid: (2S-(2 alpha,3 beta,4 beta))-2-Carboxy-4-(1-methylethenyl)-3-pyrrolidineacetic acid. Ascaricide obtained from the red alga Digenea simplex. It is a potent excitatory amino acid agonist at some types of excitatory amino acid receptors and has been used to discriminate among receptor types. Like many excitatory amino acid agonists it can cause neurotoxicity and has been used experimentally for that purpose.	7.52	2	0	dicarboxylic acid; L-proline derivative; non-proteinogenic L-alpha-amino acid; pyrrolidinecarboxylic acid	antinematodal drug; excitatory amino acid agonist
indole-3-carbaldehyde indole-3-carbaldehyde: metabolite of tryptophan; structure. indole-3-carbaldehyde : A heteroarenecarbaldehyde that is indole in which the hydrogen at position 3 has been replaced by a formyl group.	2.02	1	0	heteroarenecarbaldehyde; indole alkaloid; indoles	bacterial metabolite; human xenobiotic metabolite; marine metabolite; plant metabolite
topanol 354 Topanol 354: structure	3.25	1	0	methoxybenzenes; phenols
arecaidine [no description available]	2.1	1	0	citraconoyl group
carvacrol carvacrol : A phenol that is a natural monoterpene derivative of cymene. An inhibitor of bacterial growth, it is used as a food additive. Potent activator of the human ion channels transient receptor potential V3 (TRPV3) and A1 (TRPA1).	4.8	9	0	botanical anti-fungal agent; p-menthane monoterpenoid; phenols	agrochemical; antimicrobial agent; flavouring agent; TRPA1 channel agonist; volatile oil component
dipicolinic acid dipicolinic acid : A pyridinedicarboxylic acid carrying two carboxy groups at positions 2 and 6.	2.17	1	0	pyridinedicarboxylic acid	bacterial metabolite
4-hydroxyphenylethanol 4-hydroxyphenylethanol: in chest gland secretion of galagos. 2-(4-hydroxyphenyl)ethanol : A phenol substituted at position 4 by a 2-hydroxyethyl group.	3.49	7	0	phenols	anti-arrhythmia drug; antioxidant; cardiovascular drug; fungal metabolite; geroprotector; plant metabolite; protective agent
phloretic acid phloretic acid: structure. N-hydroxysuccinimide ester : An ester of N-hydroxysuccinimide.. phloretic acid : A hydroxy monocarboxylic acid consisting of propionic acid having a 4-hydroxyphenyl group at the 3-position.	2.59	2	0	hydroxy monocarboxylic acid	plant metabolite
azetidine [no description available]	2.1	1	0	azacycloalkane; azetidines; saturated organic heteromonocyclic parent
alpha-aminopyridine alpha-aminopyridine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #485. aminopyridine : Compounds containing a pyridine skeleton substituted by one or more amine groups.	2.37	2	0
thiazolidines Thiazolidines: Reduced (protonated) form of THIAZOLES. They can be oxidized to THIAZOLIDINEDIONES.	1.97	1	0	thiazolidine
hexacosanoic acid hexacosanoic acid: a C(26) saturated acid. hexacosanoic acid : A 26-carbon, straight-chain, saturated fatty acid.	2.01	1	0	fatty acid 26:0; straight-chain saturated fatty acid; very long-chain fatty acid
oleanolic acid [no description available]	5.71	25	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	plant metabolite
abietic acid abietic acid : An abietane diterpenoid that is abieta-7,13-diene substituted by a carboxy group at position 18.	2.01	1	0	abietane diterpenoid; monocarboxylic acid	plant metabolite
hematoxylin Hematoxylin: A dye obtained from the heartwood of logwood (Haematoxylon campechianum Linn., Leguminosae) used as a stain in microscopy and in the manufacture of ink.	2.33	2	0	organic heterotetracyclic compound; oxacycle; polyphenol; tertiary alcohol	histological dye; plant metabolite
podophyllotoxin Podophyllum: A genus of poisonous American herbs, family BERBERIDACEAE. The roots yield PODOPHYLLOTOXIN and other pharmacologically important agents. The plant was formerly used as a cholagogue and cathartic. It is different from the European mandrake, MANDRAGORA.	2.9	4	0	furonaphthodioxole; lignan; organic heterotetracyclic compound	antimitotic; antineoplastic agent; keratolytic drug; microtubule-destabilising agent; plant metabolite; tubulin modulator
hesperidin Hesperidin: A flavanone glycoside found in CITRUS fruit peels.. hesperidin : A disaccharide derivative that consists of hesperetin substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	7.78	3	0	3'-hydroxyflavanones; 4'-methoxyflavanones; dihydroxyflavanone; disaccharide derivative; flavanone glycoside; monomethoxyflavanone; rutinoside	mutagen
androstenediol Androstenediol: An intermediate in TESTOSTERONE biosynthesis, found in the TESTIS or the ADRENAL GLANDS. Androstenediol, derived from DEHYDROEPIANDROSTERONE by the reduction of the 17-keto group (17-HYDROXYSTEROID DEHYDROGENASES), is converted to TESTOSTERONE by the oxidation of the 3-beta hydroxyl group to a 3-keto group (3-HYDROXYSTEROID DEHYDROGENASES).. androst-5-ene-3beta,17beta-diol : A 3beta-hydroxy-Delta(5)-steroid that is 3beta-hydroxyandrost-5-ene carrying an additional hydroxy group at position 17beta.	3.1	1	0	17beta-hydroxy steroid; 3beta-hydroxy-Delta(5)-steroid	androgen; human metabolite; mouse metabolite; radiation protective agent
dihydrotestosterone Dihydrotestosterone: A potent androgenic metabolite of TESTOSTERONE. It is produced by the action of the enzyme 3-OXO-5-ALPHA-STEROID 4-DEHYDROGENASE.. 17beta-hydroxyandrostan-3-one : A 17beta-hydroxy steroid that is testosterone in which the 4-5 double bond has been reduced to a single bond with unspecified configuration at position 5.. 17beta-hydroxy-5alpha-androstan-3-one : A 17beta-hydroxy steroid that is testosterone in which the 4,5 double bond has been reduced to a single bond with alpha-configuration at position 5.	3.53	2	0	17beta-hydroxy steroid; 17beta-hydroxyandrostan-3-one; 3-oxo-5alpha-steroid	androgen; Daphnia magna metabolite; human metabolite; mouse metabolite
luminol Luminol: 5-Amino-2,3-dihydro-1,4-phthalazinedione. Substance that emits light on oxidation. It is used in chemical determinations.	2.48	2	0
physcione physcione: structure. physcion : A dihydroxyanthraquinone that is 9,10-anthraquinone bearing hydroxy substituents at positions 1 and 8, a methoxy group at position 3, and a methyl group at position 6. It has been widely isolated and characterised from both terrestrial and marine sources.	2.77	3	0	dihydroxyanthraquinone	anti-inflammatory agent; antibacterial agent; antifungal agent; antineoplastic agent; apoptosis inducer; hepatoprotective agent; metabolite
n-hydroxyphthalimide N-hydroxyphthalimide: causes contact dermititis	2.17	1	0
ricinine [no description available]	2.07	1	0	nitrile; pyridine alkaloid; pyridone
flavone flavone: RN given refers to unlabeled cpd; structure given in first source. flavone : The simplest member of the class of flavones that consists of 4H-chromen-4-one bearing a phenyl substituent at position 2.	4.33	5	0	flavones	metabolite; nematicide
gluconic acid gluconic acid: zinc gluconate has anti-inflammatory activity; RN given refers to (D)-isomer; all RRs refers to (D)-isomer unless otherwise noted. ketogluconic acid : A gluconic acid that contains a ketonic carbonyl group.. D-gluconic acid : A gluconic acid having D-configuration.	2.1	1	0	gluconic acid	chelator; Penicillium metabolite
copper gluconate Gluconates: Derivatives of gluconic acid (the structural formula HOCH2(CHOH)4COOH), including its salts and esters.	1.95	1	0	organic molecular entity
2,4,6-trimethylphenol [no description available]	3.25	1	0	hydroxytoluene
gallacetophenone gallacetophenone: structure in first source	2.43	2	0	aromatic ketone
1,2,3,4-tetrahydro-1-naphthalenol 1,2,3,4-tetrahydro-1-naphthalenol: structure in first source	3.1	1	0
syringic acid syringic acid: RN given refers to parent cpd; structure in third source. syringic acid : A dimethoxybenzene that is 3,5-dimethyl ether derivative of gallic acid.	11.03	245	2	benzoic acids; dimethoxybenzene; phenols	plant metabolite
hydroxyhydroquinone benzene-1,2,4-triol : A benzenetriol carrying hydroxy groups at positions 1, 2 and 4.	2	1	0	benzenetriol	mouse metabolite
tropolone Tropolone: A seven-membered aromatic ring compound. It is structurally related to a number of naturally occurring antifungal compounds (ANTIFUNGAL AGENTS).. tropolone : A cyclic ketone that is cyclohepta-2,4,6-trien-1-one substituted by a hydroxy group at position 2. It is a toxin produced by the agricultural pathogen Burkholderia plantarii.	1.95	1	0	alpha-hydroxy ketone; cyclic ketone; enol	bacterial metabolite; fungicide; toxin
methamphetamine Methamphetamine: A central nervous system stimulant and sympathomimetic with actions and uses similar to DEXTROAMPHETAMINE. The smokable form is a drug of abuse and is referred to as crank, crystal, crystal meth, ice, and speed.. methamphetamine : A member of the class of amphetamines in which the amino group of (S)-amphetamine carries a methyl substituent.	2.1	1	0	amphetamines; secondary amine	central nervous system stimulant; environmental contaminant; neurotoxin; psychotropic drug; xenobiotic
4-iodophenol [no description available]	3.1	1	0	iodophenol
uranyl acetate uranyl acetate: used after fixation in uranaffin procedure; RN given refers to parent cpd	7.47	2	0
malondialdehyde Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.	10.33	50	0	dialdehyde	biomarker
myristic acid Myristic Acid: A saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. It is used to synthesize flavor and as an ingredient in soaps and cosmetics. (From Dorland, 28th ed). tetradecanoic acid : A straight-chain, fourteen-carbon, long-chain saturated fatty acid mostly found in milk fat.. tetradecanoate : A long-chain fatty acid anion that is the conjugate base of myristic acid; major species at pH 7.3.	3.53	2	0	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite
trinitrobenzenesulfonic acid Trinitrobenzenesulfonic Acid: A reagent that is used to neutralize peptide terminal amino groups.. 2,4,6-trinitrobenzenesulfonic acid : The arenesulfonic acid that is benzenesulfonic acid with three nitro substituents in the 2-, 4- and 6-positions.	2.48	2	0	arenesulfonic acid; C-nitro compound	epitope; explosive; reagent
gentian violet Gentian Violet: A dye that is a mixture of violet rosanilinis with antibacterial, antifungal, and anthelmintic properties.. crystal violet : An organic chloride salt that is the monochloride salt of crystal violet cation. It has been used in creams for the topical treatment of bacterial and fungal infections, being effective against some Gram-positive bacteria (notably Staphylococcus species) and some pathogenic fungi (including Candida species) but use declined following reports of animal carcinogenicity. It has also been used for dying wood, silk, and paper, as well as a histological stain.	2.6	1	0	organic chloride salt	anthelminthic drug; antibacterial agent; antifungal agent; antiseptic drug; histological dye
aminopenicillanic acid aminopenicillanic acid: RN given refers to parent cpd; structure. 6-aminopenicillanic acid : A penicillanic acid compound having a (6R)-amino substituent. The active nucleus common to all penicillins, it may be substituted at the 6-amino position to form the semisynthetic penicillins, resulting in a variety of antibacterial and pharmacologic characteristics.	2.1	1	0	amino acid zwitterion; penicillanic acids	allergen
paeonol paeonol: structure	3.86	11	0	methoxybenzenes; phenols	metabolite
neutral red Neutral Red: A vital dye used as an indicator and biological stain. Various adverse effects have been observed in biological systems.. neutral red : A hydrochloride obtained by combining the free base of neutral red with one equivalent of hydrochloric acid. Neutral red acts as a pH indicator, changing from red to yellow between pH 6.8 and 8.0.	2.46	2	0	hydrochloride	acid-base indicator; dye; two-colour indicator
glycyl-glycyl-glycine glycyl-glycyl-glycine : A tripeptide in which three glycine units are linked via peptide bonds in a linear sequence.	2.1	1	0	tripeptide zwitterion; tripeptide
diethylzinc [no description available]	7.11	1	0
18-hydroxycorticosterone [no description available]	1.97	1	0	11beta-hydroxy steroid; 18-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo steroid; primary alpha-hydroxy ketone	human metabolite; mouse metabolite
4-methyl-1-(1-methylethyl)-3-cyclohexen-1-ol 4-methyl-1-(1-methylethyl)-3-cyclohexen-1-ol: structure in first source. 4-terpineol : A terpineol that is 1-menthene carrying a hydroxy substituent at position 4.	3.52	2	0	terpineol; tertiary alcohol	anti-inflammatory agent; antibacterial agent; antineoplastic agent; antioxidant; antiparasitic agent; apoptosis inducer; plant metabolite; volatile oil component
2-hydroxybutyric acid 2-hydroxybutyric acid: RN given refers to cpd without isomeric designation. hydroxybutyric acid : Any compound comprising a butyric acid core carrying at least one hydroxy substituent.. 2-hydroxybutyric acid : A hydroxybutyric acid having a single hydroxyl group located at position 2; urinary secretion of 2-hydroxybutyric acid is increased with alcohol ingestion or vigorous physical exercise and is associated with lactic acidosis and ketoacidosis in humans and diabetes in animals.	2.13	1	0	2-hydroxy monocarboxylic acid; hydroxybutyric acid	algal metabolite; human metabolite
formestane [no description available]	2.1	1	0	17-oxo steroid; 3-oxo-Delta(4) steroid; enol; hydroxy steroid	antineoplastic agent; EC 1.14.14.14 (aromatase) inhibitor
3-hydroxyflavone 3-hydroxyflavone: structure given in first source. flavonol : A monohydroxyflavone that is the 3-hydroxy derivative of flavone.	5.98	32	0	flavonols; monohydroxyflavone
6-hydroxyquinoline quinolin-6-ol : A monohydroxyquinoline that is quinoline substituted by a hydroxy group at position 6.	3.1	1	0	monohydroxyquinoline
3-hydroxybiphenyl 3-hydroxybiphenyl: structure given in first source. biphenyl-3-ol : A member of the class of hydroxybiphenyls that is phenol in which the hydrogen at position 3 has been replaced by a phenyl group.	3.1	1	0	hydroxybiphenyls
3-methoxybenzoic acid [no description available]	1.98	1	0	methoxybenzoic acid	flavouring agent; human urinary metabolite
diphenylamine Diphenylamine: In humans it may be irritating to mucous membranes. Methemoglobinemia has been produced experimentally. In veterinary use, it is one of active ingredients in topical agents for prevention and treatment of screwworm infestation. An indicator in tests for nitrate poisoning.. diphenylamine : An aromatic amine containing two phenyl substituents. It has been used as a fungicide for the treatment of superficial scald in apples and pears, but is no longer approved for this purpose within the European Union.	3.1	1	0	aromatic amine; bridged diphenyl fungicide; secondary amino compound	antifungal agrochemical; antioxidant; carotogenesis inhibitor; EC 1.3.99.29 [phytoene desaturase (zeta-carotene-forming)] inhibitor; ferroptosis inhibitor; radical scavenger
n-methylphenethylamine N-methylphenethylamine: substrate for type A & B monoamine oxidase; RN given refers to parent cpd	2.17	1	0
methylurea N-methyl urea : A member of the class of ureas that is urea substituted by a methyl group at one of the nitrogen atoms.	1.96	1	0	ureas
n,n-dimethylethylamine [no description available]	2.1	1	0
triphenylphosphine triphenylphosphine: RN given refers to parent cpd. triphenylphosphine : A member of the class of tertiary phosphines that is phosphane in which the three hydrogens are replaced by phenyl groups.	2.1	1	0	benzenes; tertiary phosphine	NMR chemical shift reference compound; reducing agent
alpha-naphthoflavone alpha-naphthoflavone: inhibits P4501A1 and P4501A2; stimulates some activities of P4503A4. alpha-naphthoflavone : An extended flavonoid resulting from the formal fusion of a benzene ring with the h side of flavone. A synthetic compound, it is an inhibitor of aromatase (EC 1.14.14.14).	3.5	2	0	extended flavonoid; naphtho-gamma-pyrone; organic heterotricyclic compound	aryl hydrocarbon receptor agonist; aryl hydrocarbon receptor antagonist; EC 1.14.14.14 (aromatase) inhibitor
galactitol [no description available]	1.96	1	0	hexitol	Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite
2,3,4-Trihydroxybenzoic acid [no description available]	2.76	3	0	hydroxybenzoic acid
2-anthramine 2-anthramine: structure	2.01	1	0	anthracenamine
diethylmethylamine [no description available]	2.1	1	0
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	5.46	19	0	acetylcysteine; L-cysteine derivative; N-acetyl-L-amino acid	antidote to paracetamol poisoning; antiinfective agent; antioxidant; antiviral drug; ferroptosis inhibitor; geroprotector; human metabolite; mucolytic; radical scavenger; vulnerary
benzenesulfinic acid [no description available]	2.21	1	0	organosulfinic acid
4-ethylbenzoic acid [no description available]	2	1	0	benzoic acids
5-methyl-2-furfural 5-methyl-2-furfural: RN given refers to cpd with locants as specified	2.07	1	0	aldehyde; furans	EC 2.2.1.6 (acetolactate synthase) inhibitor; flavouring agent; human metabolite; Maillard reaction product
3-hydroxybenzeneacetic acid 3-hydroxybenzeneacetic acid: metabolite of L-dopa; structure. 3-hydroxyphenylacetic acid : A monocarboxylic acid that is phenylacetic acid in which the hydrogen at position 3 on the benzene ring is replaced by a hydroxy group.	5.35	2	2	monocarboxylic acid; phenols	human xenobiotic metabolite
glycine ethyl ester glycine ethyl ester: RN given refers to parent cpd	2.1	1	0
n-methylpiperidine N-methylpiperidine: RN given refers to parent cpd	2.1	1	0
nonacosane nonacosane: constituent of Apocynum venetum leaf. nonacosane : A straight-chain alkane comprising of 29 carbon atoms.	2.04	1	0	long-chain alkane	plant metabolite; volatile oil component
hentriacontane [no description available]	2.04	1	0	long-chain alkane	antitubercular agent
Berberine chloride (TN) [no description available]	2.07	1	0	organic molecular entity
benzydamine Benzydamine: A benzyl-indazole having analgesic, antipyretic, and anti-inflammatory effects. It is used to reduce post-surgical and post-traumatic pain and edema and to promote healing. It is also used topically in treatment of RHEUMATIC DISEASES and INFLAMMATION of the mouth and throat.. benzydamine : A member of the class of indazoles carrying benzyl and 3-(dimethylamino)propyl groups at positions 1 and 3 respectively. A locally-acting nonsteroidal anti-inflammatory drug that also exhibits local anaesthetic and analgesic properties.	2.1	1	0	aromatic ether; indazoles; tertiary amino compound	analgesic; central nervous system stimulant; hallucinogen; local anaesthetic; non-steroidal anti-inflammatory drug
erythromycin Erythromycin: A bacteriostatic antibiotic macrolide produced by Streptomyces erythreus. Erythromycin A is considered its major active component. In sensitive organisms, it inhibits protein synthesis by binding to 50S ribosomal subunits. This binding process inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins.. erythromycin : Any of several wide-spectrum macrolide antibiotics obtained from actinomycete Saccharopolyspora erythraea (formerly known as Streptomyces erythraeus).. erythromycin A : An erythromycin that consists of erythronolide A having 2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl and 3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl residues attahced at positions 4 and 6 respectively.	4.77	6	1	cyclic ketone; erythromycin
precocene ii precocene II: has antibacterial, antifungal, insecticidal, and antioxidant activities; from plants of genus Ageratum; an antiallotropin compound capable of inhibiting juvenile hormone biosynthesis	3.23	1	0	chromenes	precocenes
isovanillic acid 3-hydroxy-4-methoxybenzoic acid : A methoxybenzoic acid that is 4-methoxybenzoic acid bearing a hydroxy substituent at position 3.	3.14	5	0	methoxybenzoic acid; monohydroxybenzoic acid	antibacterial agent; plant metabolite
4-propylphenol 4-propylphenol: structure given in first source	3.1	1	0	alkylbenzene
2-piperidone 2-piperidone: structure given in first source. piperidin-2-one : A delta-lactam that is piperidine which is substituted by an oxo group at position 2.	1.96	1	0	delta-lactam; piperidones	EC 1.2.1.88 (L-glutamate gamma-semialdehyde dehydrogenase) inhibitor
methylnitrosourea Methylnitrosourea: A nitrosourea compound with alkylating, carcinogenic, and mutagenic properties.. N-methyl-N-nitrosourea : A member of the class of N-nitrosoureas that is urea in which one of the nitrogens is substituted by methyl and nitroso groups.	1.97	1	0	N-nitrosoureas	alkylating agent; carcinogenic agent; mutagen; teratogenic agent
diphenyliodonium diphenyliodonium: RN given refers to the parent coumpound; inhibitor of neutrophil superoxide generating oxidase; structure has been determined	1.99	1	0
4-methylimidazole 4-methylimidazole: RN given refers to parent cpd. 4-methylimidazole : Imidazole substituted at position 4 by a methyl group.	2.13	1	0	imidazoles	carcinogenic agent; reaction intermediate
tempidon 2,2,6,6-tetramethyl-4-piperidinone: structure in first source	2.1	1	0	piperidones
ethyl gallate ethyl gallate: used with osmium in procedure for mapping neuronal pathways. ethyl gallate : A gallate ester obtained by the formal condensation of gallic acid with ethanol.	11.85	81	0	gallate ester	plant metabolite
amaranth dye Amaranth Dye: A sulfonic acid-based naphthylazo dye used as a coloring agent for foodstuffs and medicines and as a dye and chemical indicator. It was banned by the FDA in 1976 for use in foods, drugs, and cosmetics. (From Merck Index, 11th ed)	2.07	1	0
hexafluoroisopropanol 1,1,1,3,3,3-hexafluoropropan-2-ol : An organofluorine compound formed by substitution of all the methyl protons in propan-2-ol by fluorine. It is a metabolite of inhalation anesthetic sevoflurane.	3.1	1	0	organofluorine compound; secondary alcohol	drug metabolite
nitrosobenzylmethylamine nitrosobenzylmethylamine: structure	1.99	1	0
deoxycytidine [no description available]	2.06	1	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
2,6-dichloroindophenol 2,6-Dichloroindophenol: A dye used as a reagent in the determination of vitamin C.. 2,6-dichloroindophenol : A quinone imine that is indophenol substituted by chloro groups at positions 2 and 6.. N-3,5-dichloro-4-hydroxyphenyl-1,4-benzoquinone imine : 1,4-benzoquinone imine having a 3,5-dichloro-4-hydroxyphenyl substituent attached to the nitrogen atom.	2.06	1	0	dichlorobenzene; quinone imine
rhodamine 6g rhodamine 6G: RN given refers to HCl	2.05	1	0
5-methoxyindole 5-methoxyindole: structure in first source	2.08	1	0	indoles
n-butyl gallate [no description available]	3.41	7	0
1,3-propane sultone 1,3-propane sultone: sultone is usually defined as a derivative of 1,8-naphtholsulfonic acid; structure	1.96	1	0	sultone
dihydroferulic acid dihydroferulic acid: structure in first source. dihydroferulic acid : A monocarboxylic acid that is propanoic acid in which one of the hydrogens at position 3 has been replaced by a 4-hydroxy-3-methoxyphenyl group.	2.49	2	0	guaiacols; monocarboxylic acid; phenylpropanoid	antioxidant; human xenobiotic metabolite; mouse metabolite; plant metabolite
lauryl gallate [no description available]	7.68	62	0	gallate ester
durapatite Durapatite: The mineral component of bones and teeth; it has been used therapeutically as a prosthetic aid and in the prevention and treatment of osteoporosis.. hydroxylapatite : A phosphate mineral with the formula Ca5(PO4)3(OH).	3.38	6	0
cadmium sulfide [no description available]	7.52	2	0	cadmium molecular entity
sodium hydroxide Sodium Hydroxide: A highly caustic substance that is used to neutralize acids and make sodium salts. (From Merck Index, 11th ed)	1.94	1	0	alkali metal hydroxide
manganese dioxide [no description available]	2.21	1	0	manganese molecular entity; metal oxide
zinc oxide Zinc Oxide: A mild astringent and topical protectant with some antiseptic action. It is also used in bandages, pastes, ointments, dental cements, and as a sunblock.	3.35	6	0	zinc molecular entity
monolaurin monolaurin: RN given refers to cpd with unspecified monolaurin locant. 1-monolauroylglycerol : A 1-monoglyceride with dodecanoyl (lauroyl) as the acyl group.. rac-1-monolauroylglycerol : A rac-1-monoacylglycerol comprising equal amounts of 1-lauroyl-sn-glycerol and 3-lauroyl-sn-glycerol	2.05	1	0	1-monoglyceride; dodecanoate ester; rac-1-monoacylglycerol
ferrous oxide [no description available]	2.21	1	0	iron oxide
vancomycin Vancomycin: Antibacterial obtained from Streptomyces orientalis. It is a glycopeptide related to RISTOCETIN that inhibits bacterial cell wall assembly and is toxic to kidneys and the inner ear.. vancomycin : A complex glycopeptide from Streptomyces orientalis. It inhibits a specific step in the synthesis of the peptidoglycan layer in the Gram-positive bacteria Staphylococcus aureus and Clostridium difficile.	2.83	3	0	glycopeptide	antibacterial drug; antimicrobial agent; bacterial metabolite
glycyrrhizic acid glycyrrhizinic acid : A triterpenoid saponin that is the glucosiduronide derivative of 3beta-hydroxy-11-oxoolean-12-en-30-oic acid.	8.33	5	0	enone; glucosiduronic acid; pentacyclic triterpenoid; tricarboxylic acid; triterpenoid saponin	EC 3.4.21.5 (thrombin) inhibitor; plant metabolite
d-alpha tocopherol Vitamin E: A generic descriptor for all TOCOPHEROLS and TOCOTRIENOLS that exhibit ALPHA-TOCOPHEROL activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of ISOPRENOIDS.. tocopherol : A collective name for a group of closely related lipids that contain a chroman-6-ol nucleus substituted at position 2 by a methyl group and by a saturated hydrocarbon chain consisting of three isoprenoid units. They are designated as alpha-, beta-, gamma-, and delta-tocopherol depending on the number and position of additional methyl substituents on the aromatic ring. Tocopherols occur in vegetable oils and vegetable oil products, almost exclusively with R,R,R configuration. Tocotrienols differ from tocopherols only in having three double bonds in the hydrocarbon chain.. vitamin E : Any member of a group of fat-soluble chromanols that exhibit biological activity against vitamin E deficiency. The vitamers in this class consists of a chroman-6-ol core which is substituted at position 2 by a methyl group and (also at position 2) either a saturated or a triply-unsaturated hydrocarbon chain consisting of three isoprenoid units. The major function of vitamin E is to act as a natural antioxidant by scavenging free radicals and molecular oxygen.. (R,R,R)-alpha-tocopherol : An alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils.	7.74	49	0	alpha-tocopherol	algal metabolite; antiatherogenic agent; anticoagulant; antioxidant; antiviral agent; EC 2.7.11.13 (protein kinase C) inhibitor; immunomodulator; micronutrient; nutraceutical; plant metabolite
tocopherols [no description available]	4.25	5	0
fenchol fenchol: RN given refers to cpd with unspecified isomeric designation	3.1	1	0
4-n-Butylphenol [no description available]	3.1	1	0	phenols
4-hydroxyazobenzene 4-hydroxyazobenzene: structure in first source	3.1	1	0
clopyralid clopyralid : An organochlorine pesticide having a 3,6-dichlorinated picolinic acid structure.	2.1	1	0	organochlorine pesticide; pyridines	herbicide
dimethylaminopropionitrile [no description available]	2.1	1	0
4-nitrothiophenolate 4-nitrothiophenolate: RN given refers to parent cpd	3.1	1	0
5 alpha-androstane-3 alpha,17 beta-diol 5alpha-androstane-3alpha,17beta-diol : The 5alpha-stereoisomer of androstane-3alpha,17beta-diol.	3.1	1	0	androstane-3alpha,17beta-diol	Daphnia magna metabolite; human metabolite
paraquat Paraquat: A poisonous dipyridilium compound used as contact herbicide. Contact with concentrated solutions causes irritation of the skin, cracking and shedding of the nails, and delayed healing of cuts and wounds.. paraquat : An organic cation that consists of 4,4'-bipyridine bearing two N-methyl substituents loctated at the 1- and 1'-positions.	7.31	1	0	organic cation	geroprotector; herbicide
orange g orange G : An organic sodium salt that is the disodium salt of 7-hydroxy-8-[(E)-phenyldiazenyl]naphthalene-1,3-disulfonic acid. It is often combined with other yellow dyes in alcoholic solution to stain erythrocytes in trichrome methods, and is used for demonstrating cells in the pancreas and pituitary.	2.21	1	0
tetrabutylammonium tetrabutylammonium: lipophilic probe; RN given refers to parent cpd	2.06	1	0	quaternary ammonium ion
2-tert-butylhydroquinone 2-tert-butylhydroquinone: an anticarcinogenic and chemopreventive agent. 2-tert-butylhydroquinone : A member of the class of hydroquinones in which one of the ring hydrogens of hydroquinone is replaced by a tert-butyl group.	3.29	6	0	hydroquinones	food antioxidant
5-hydroxyindole [no description available]	2.49	2	0	hydroxyindoles	human metabolite
amiloride Amiloride: A pyrazine compound inhibiting SODIUM reabsorption through SODIUM CHANNELS in renal EPITHELIAL CELLS. This inhibition creates a negative potential in the luminal membranes of principal cells, located in the distal convoluted tubule and collecting duct. Negative potential reduces secretion of potassium and hydrogen ions. Amiloride is used in conjunction with DIURETICS to spare POTASSIUM loss. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p705). amiloride : A member of the class of pyrazines resulting from the formal monoacylation of guanidine with the carboxy group of 3,5-diamino-6-chloropyrazine-2-carboxylic acid.	5.01	13	0	aromatic amine; guanidines; organochlorine compound; pyrazines	diuretic; sodium channel blocker
pimozide Pimozide: A diphenylbutylpiperidine that is effective as an antipsychotic agent and as an alternative to HALOPERIDOL for the suppression of vocal and motor tics in patients with Tourette syndrome. Although the precise mechanism of action is unknown, blockade of postsynaptic dopamine receptors has been postulated. (From AMA Drug Evaluations Annual, 1994, p403). pimozide : A member of the class of benzimidazoles that is 1,3-dihydro-2H-benzimidazol-2-one in which one of the nitrogens is substituted by a piperidin-4-yl group, which in turn is substituted on the nitrogen by a 4,4-bis(p-fluorophenyl)butyl group.	2.4	2	0	benzimidazoles; heteroarylpiperidine; organofluorine compound	antidyskinesia agent; dopaminergic antagonist; first generation antipsychotic; H1-receptor antagonist; serotonergic antagonist
1,6-diaminohexane 1,6-diaminohexane: Russian drug; RN given refers to parent cpd; structure. hexane-1,6-diamine : A C6 alkane-alpha,omega-diamine.	2.51	2	0	alkane-alpha,omega-diamine	human xenobiotic metabolite
menthol (+-)-menthol : A racemate comprising equimolar amounts of (+)- and (-)-menthol. Both (+-)- and (-)-menthol are used to relieve symptoms of conditions such as bronchitis and sinusitis. When applied to the skin, menthol dilates the blood vessels, giving a sensation of coldness followed by an analgesic effect that relieves itching. It is therefore used in creams and ointments for the relief of pruritis and urticaria.. (-)-menthol : A p-menthan-3-ol which has (1R,2S,5R)-stereochemistry. It is the most common naturally occurring enantiomer.	3.51	2	0	p-menthan-3-ol	antipruritic drug; antispasmodic drug; antitussive
5-phenylvaleric acid 5-phenylvaleric acid: from Polygonum salicifolium. 5-phenylpentanoic acid : A monocarboxylic acid that is valeric acid substituted by a phenyl group at the delta-position.	2.1	1	0	benzenes; monocarboxylic acid
fluorescein Fluorescein: A phthalic indicator dye that appears yellow-green in normal tear film and bright green in a more alkaline medium such as the aqueous humor.. fluorescein (lactone form) : A xanthene dye that is highly fluorescent, detectable even when present in minute quantities. Used forensically to detect traces of blood, in analytical chemistry as an indicator in silver nitrate titrations and in microscopy.	2.69	3	0	2-benzofurans; gamma-lactone; organic heteropentacyclic compound; oxaspiro compound; polyphenol; xanthene dye	fluorescent dye; radioopaque medium
thioflavin t thioflavin T: RN given refers to chloride; structure. thioflavine T : An organic chloride salt having 2-[4-(dimethylamino)phenyl]-3,6-dimethyl-1,3-benzothiazol-3-ium as the counterion. It is widely used to visualise and quantify the presence of amyloids, both in vitro and in vivo.	2.78	3	0	organic chloride salt	fluorochrome; geroprotector; histological dye
acetosyringone acetosyringone: plant inducer which induces expression of VirE & VirG in A. tumefaciens. acetosyringone : A member of the class of acetophenones that is 1-phenylethanone substituted by a hydroxy group at position 4 and methoxy groups at positions 3 and 5.	2.44	2	0	acetophenones; dimethoxybenzene; phenols	anti-asthmatic drug; non-narcotic analgesic; non-steroidal anti-inflammatory drug; peripheral nervous system drug; plant metabolite
hydroxyphenytoin hydroxyphenytoin: main metabolite of diphenylhydantoin; reduces Na(+) inhibition at high Na:K ratios; RN given refers to cpd without isomeric designation; structure. 4-hydroxyphenytoin : A imidazolidine-2,4-dione that consists of hydantoin bearing phenyl and 4-hydroxyphenyl substituents at position 5.	3.1	1	0	imidazolidine-2,4-dione; phenols	metabolite
isophorone diamine isophorone diamine: curing agent for polymers; structure given in first source; RN given refers to parent cpd	2.21	1	0
methional [no description available]	1.97	1	0	aliphatic sulfide	prostaglandin antagonist
fluorescein-5-isothiocyanate Fluorescein-5-isothiocyanate: Fluorescent probe capable of being conjugated to tissue and proteins. It is used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.. fluorescein 5-isothiocyanate : The 5-isomer of fluorescein isothiocyanate. Acts as a fluorescent probe capable of being conjugated to tissue and proteins; used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.	1.96	1	0	fluorescein isothiocyanate
sabinene sabinene: RN given refers to cpd without isomeric designation. sabinene : A thujene that is a bicyclic monoterpene isolated from the essential oils of various plant species.	3.78	10	0	thujene	plant metabolite
mannose mannopyranose : The pyranose form of mannose.	2.75	3	0	D-aldohexose; D-mannose; mannopyranose	metabolite
dithiothreitol 1,4-dimercaptobutane-2,3-diol : A glycol that is butane-2,3-diol in which a hydrogen from each of the methyl groups is replaced by a thiol group.. 1,4-dithiothreitol : The threo-diastereomer of 1,4-dimercaptobutane-2,3-diol.	2.9	4	0	1,4-dimercaptobutane-2,3-diol; butanediols; dithiol; glycol; thiol	chelator; human metabolite; reducing agent
cyclacillin Cyclacillin: A cyclohexylamido analog of PENICILLANIC ACID.	2.1	1	0	penicillin	antibacterial drug
cyclic cmp Cyclic CMP: A cyclic nucleotide formed from CYTIDINE TRIPHOSPHATE by the action of cytidylate cyclase. It is a potential cyclic nucleotide intracellular mediator of signal transductions.. 3',5'-cyclic CMP : A 3',5'-cyclic pyrimidine nucleotide having cytosine as the nucleobase.	1.99	1	0	3',5'-cyclic pyrimidine nucleotide	human metabolite
acedoben 4-acetamidobenzoic acid : A amidobenzoic acid that consists of benzoic acid bearing an acetamido substituent at position 4.	2.05	1	0	amidobenzoic acid
3-phenoxybenzoic acid 3-phenoxybenzoic acid: metabolite associated with exposure to pyrethroid insecticides. 3-phenoxybenzoic acid : A phenoxybenzoic acid in which the phenoxy group is meta to the carboxy group. It is a metabolite of pyrethroid insecticides.	2.25	1	0	phenoxybenzoic acid	human xenobiotic metabolite; marine xenobiotic metabolite
streptomycin [no description available]	3.08	5	0	antibiotic antifungal drug; antibiotic fungicide; streptomycins	antibacterial drug; antifungal agrochemical; antimicrobial agent; antimicrobial drug; bacterial metabolite; protein synthesis inhibitor
carbonates Carbonates: Salts or ions of the theoretical carbonic acid, containing the radical CO2(3-). Carbonates are readily decomposed by acids. The carbonates of the alkali metals are water-soluble; all others are insoluble. (From Grant & Hackh's Chemical Dictionary, 5th ed). carbonates : Organooxygen compounds that are salts or esters of carbonic acid, H2CO3.	3.04	1	0	carbon oxoanion
butylhydroxybutylnitrosamine Butylhydroxybutylnitrosamine: A substituted carcinogenic nitrosamine.. N-butyl-N-(4-hydroxybutyl)nitrosamine : A nitrosamine that has butyl and 4-hydroxybutyl substituents. In mice, it causes high-grade, invasive cancers in the urinary bladder, but not in any other tissues.	1.97	1	0	nitrosamine; primary alcohol	carcinogenic agent
3-o-methylgallic acid 3-O-methylgallic acid: structure in first source. 3-O-methylgallic acid : A member of the class of benzoic acids that is gallic acid in which the phenolic hydroxy group at position 3 is converted into the corresponding methyl ether.	8.28	21	1	benzoic acids; catechols
methyl vanillate methyl vanillate: isolated from Hovenia dulcis. methyl vanillate : A benzoate ester that is the methyl ester of vanillic acid.	2.41	1	0	aromatic ether; benzoate ester; phenols	antioxidant; plant metabolite
cocamidopropyl betaine cocamidopropyl betaine: structure given in first source; Genagen CAB, Tego Betain, Rewoteric AMB 14 usually contain 30% cocamidopropyl betaine (CAPB). cocamidopropyl betaine : A mixture of carboxamidopropyl betaines derived from fatty acids of varying chain lengths. The principal component is lauramidopropyl betaine.. lauramidopropyl betaine : An ammonium betaine in which the the ammonium nitrogen is substituted by two methyl groups and a lauramidopropyl group. It is the major (>50%) component of cocamidopropyl betaine.	2.1	1	0	ammonium betaine	surfactant
mono-(2-ethylhexyl)phthalate mono-(2-ethylhexyl)phthalate: RN given refers to parent cpd. mono(2-ethylhexyl) phthalate : The mono(2-ethylhexyl) ester of benzene-1,2-dicarboxylic acid.	3.1	1	0	phthalic acid monoester
fructosamine Fructosamine: An amino sugar formed when glucose non-enzymatically reacts with the N-terminal amino group of proteins. The fructose moiety is derived from glucose by the classical Amadori rearrangement.	2.13	1	0
tabersonine [no description available]	2.17	1	0	alkaloid ester; methyl ester; monoterpenoid indole alkaloid; organic heteropentacyclic compound	antineoplastic agent; metabolite
carbenicillin Carbenicillin: Broad-spectrum semisynthetic penicillin derivative used parenterally. It is susceptible to gastric juice and penicillinase and may damage platelet function.. carbenicillin : A penicillin antibiotic having a 6beta-2-carboxy-2-phenylacetamido side-chain.	7.11	1	0	penicillin allergen; penicillin	antibacterial drug
1-naphthalenemethanol 1-naphthalenemethanol: structure given in first source. (1-naphthyl)methanol : A naphthylmethanol that is methanol in which one of the hydrogens of the methyl group is replaced by a naphthalen-1-yl group.	3.1	1	0	naphthylmethanol	mouse metabolite
dexpropranolol [no description available]	3.1	1	0	propranolol
buthionine sulfoximine Buthionine Sulfoximine: A synthetic amino acid that depletes glutathione by irreversibly inhibiting gamma-glutamylcysteine synthetase. Inhibition of this enzyme is a critical step in glutathione biosynthesis. It has been shown to inhibit the proliferative response in human T-lymphocytes and inhibit macrophage activation. (J Biol Chem 1995;270(33):1945-7). 2-amino-4-(S-butylsulfonimidoyl)butanoic acid : A non-proteinogenic alpha-amino acid that is homocysteine in which the thiol group carries an oxo, imino and butyl groups.. S-butyl-DL-homocysteine (S,R)-sulfoximine : A sulfoximide that is the sulfoximine derivative of an analogue of DL-methionine in which the S-methyl group is replaced by S-butyl.	2.78	3	0	diastereoisomeric mixture; homocysteines; non-proteinogenic alpha-amino acid; sulfoximide	EC 6.3.2.2 (glutamate--cysteine ligase) inhibitor; ferroptosis inducer
1-nitropyrene [no description available]	2.41	1	0	nitroarene	carcinogenic agent
limonene Limonene: A naturally-occurring class of MONOTERPENES which occur as a clear colorless liquid at room temperature. Limonene is the major component in the oil of oranges which has many uses, including as flavor and fragrance. It is recognized as safe in food by the Food and Drug Administration (FDA).. limonene : A monoterpene that is cyclohex-1-ene substituted by a methyl group at position 1 and a prop-1-en-2-yl group at position 4 respectively.	9.62	5	1	cycloalkene; p-menthadiene	human metabolite
n-methylaspartate N-Methylaspartate: An amino acid that, as the D-isomer, is the defining agonist for the NMDA receptor subtype of glutamate receptors (RECEPTORS, NMDA).. N-methyl-D-aspartic acid : An aspartic acid derivative having an N-methyl substituent and D-configuration.	2.4	2	0	amino dicarboxylic acid; D-alpha-amino acid; D-aspartic acid derivative; secondary amino compound	neurotransmitter agent
3-deazaadenosine 3-deazaadenosine: RN given refers to parent cpd.	2.37	2	0
lanthanum [no description available]	4.22	18	0	f-block element atom; lanthanoid atom; scandium group element atom
manganese Manganese: A trace element with atomic symbol Mn, atomic number 25, and atomic weight 54.94. It is concentrated in cell mitochondria, mostly in the pituitary gland, liver, pancreas, kidney, and bone, influences the synthesis of mucopolysaccharides, stimulates hepatic synthesis of cholesterol and fatty acids, and is a cofactor in many enzymes, including arginase and alkaline phosphatase in the liver. (From AMA Drug Evaluations Annual 1992, p2035). manganese(4+) : A manganese cation that is monoatomic and has a formal charge of +4.	3.79	11	0	elemental manganese; manganese group element atom	Escherichia coli metabolite; micronutrient
mercury Mercury: A silver metallic element that exists as a liquid at room temperature. It has the atomic symbol Hg (from hydrargyrum, liquid silver), atomic number 80, and atomic weight 200.59. Mercury is used in many industrial applications and its salts have been employed therapeutically as purgatives, antisyphilitics, disinfectants, and astringents. It can be absorbed through the skin and mucous membranes which leads to MERCURY POISONING. Because of its toxicity, the clinical use of mercury and mercurials is diminishing.. mercury(0) : Elemental mercury of oxidation state zero.	4	4	0	elemental mercury; zinc group element atom	neurotoxin
molybdenum Molybdenum: A metallic element with the atomic symbol Mo, atomic number 42, and atomic weight 95.95. It is an essential trace element, being a component of the enzymes xanthine oxidase, aldehyde oxidase, and nitrate reductase.	3.41	7	0	chromium group element atom	micronutrient
osmium Osmium: A very hard, gray, toxic, and nearly infusible metal element, atomic number 76, atomic weight 190.2, symbol Os.	2.35	2	0	iron group element atom; platinum group metal atom
palladium Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.	2.88	3	0	metal allergen; nickel group element atom; platinum group metal atom
platinum Platinum: A heavy, soft, whitish metal, resembling tin, with atomic number 78, atomic weight 195.084, symbol Pt. It is used in manufacturing equipment for laboratory and industrial use. It occurs as a black powder (platinum black) and as a spongy substance (spongy platinum) and may have been known in Pliny's time as alutiae.	2.54	2	0	elemental platinum; nickel group element atom; platinum group metal atom
ruthenium Ruthenium: A hard, brittle, grayish-white rare earth metal with an atomic symbol Ru, atomic number 44, and atomic weight 101.07. It is used as a catalyst and hardener for PLATINUM and PALLADIUM.	8.02	4	0	iron group element atom; platinum group metal atom
silver Silver: An element with the atomic symbol Ag, atomic number 47, and atomic weight 107.87. It is a soft metal that is used medically in surgical instruments, dental prostheses, and alloys. Long-continued use of silver salts can lead to a form of poisoning known as ARGYRIA.	4.09	13	0	copper group element atom; elemental silver	Escherichia coli metabolite
tantalum Tantalum: A rare metallic element, atomic number 73, atomic weight 180.948, symbol Ta. It is a noncorrosive and malleable metal that has been used for plates or disks to replace cranial defects, for wire sutures, and for making prosthetic devices.	2.08	1	0	vanadium group element atom
titanium Titanium: A dark-gray, metallic element of widespread distribution but occurring in small amounts with atomic number, 22, atomic weight, 47.867 and symbol, Ti; specific gravity, 4.5; used for fixation of fractures.	8.69	9	0	titanium group element atom
tungsten Tungsten: A metallic element with the atomic symbol W, atomic number 74, and atomic weight 183.85. It is used in many manufacturing applications, including increasing the hardness, toughness, and tensile strength of steel; manufacture of filaments for incandescent light bulbs; and in contact points for automotive and electrical apparatus.	2.39	2	0	chromium group element atom	micronutrient
cadmium Cadmium: An element with atomic symbol Cd, atomic number 48, and atomic weight 112.41. It is a metal and ingestion will lead to CADMIUM POISONING.. elemental cadmium : An element in the zinc group of the periodic table with atomic number 48, atomic mass 112, M.P. 321degreeC, and B.P. 765degreeC). An odourless, tasteless, and highly poisonous soft, ductile, lustrous metal with electropositive properties. It has eight stable isotopes: (106)Cd, (108)Cd,(110)Cd, (111)Cd, (112)Cd, (113)Cd, (114)Cd and (116)Cd, with (112)Cd and (114)Cd being the most common.	4.61	8	0	cadmium molecular entity; zinc group element atom
cerium Cerium: An element of the rare earth family of metals. It has the atomic symbol Ce, atomic number 58, and atomic weight 140.12. Cerium is a malleable metal used in industrial applications.	3	4	0	f-block element atom; lanthanoid atom
chromium Chromium: A trace element that plays a role in glucose metabolism. It has the atomic symbol Cr, atomic number 24, and atomic weight 52. According to the Fourth Annual Report on Carcinogens (NTP85-002,1985), chromium and some of its compounds have been listed as known carcinogens.. chromium ion : An chromium atom having a net electric charge.. chromium atom : A chromium group element atom that has atomic number 24.	3.76	10	0	chromium group element atom; metal allergen	micronutrient
europium Europium: An element of the rare earth family of metals. It has the atomic symbol Eu, atomic number 63, and atomic weight 152. Europium is used in the form of its salts as coatings for cathode ray tubes and in the form of its organic derivatives as shift reagents in NMR spectroscopy.	7.57	2	0	f-block element atom; lanthanoid atom
gadolinium Gadolinium: An element of the rare earth family of metals. It has the atomic symbol Gd, atomic number 64, and atomic weight 157.25. Its oxide is used in the control rods of some nuclear reactors.	2.01	1	0	f-block element atom; lanthanoid atom
gold Gold: A yellow metallic element with the atomic symbol Au, atomic number 79, and atomic weight 197. It is used in jewelry, goldplating of other metals, as currency, and in dental restoration. Many of its clinical applications, such as ANTIRHEUMATIC AGENTS, are in the form of its salts.	4.8	28	0	copper group element atom; elemental gold
holmium Holmium: An element of the rare earth family of metals. It has the atomic symbol Ho, atomic number 67, and atomic weight 164.93.	2.04	1	0	f-block element atom; lanthanoid atom
uranium Uranium: A radioactive element of the actinide series of metals. It has an atomic symbol U, atomic number 92, and atomic weight 238.03. U-235 is used as the fissionable fuel in nuclear weapons and as fuel in nuclear power reactors.	1.97	1	0	actinoid atom; f-block element atom; monoatomic uranium
vanadium Vanadium: A metallic element with the atomic symbol V, atomic number 23, and atomic weight 50.94. It is used in the manufacture of vanadium steel. Prolonged exposure can lead to chronic intoxication caused by absorption usually via the lungs.	2.69	3	0	elemental vanadium; vanadium group element atom	micronutrient
ytterbium Ytterbium: An element of the rare earth family of metals. It has the atomic symbol Yb, atomic number 70, and atomic weight 173. Ytterbium has been used in lasers and as a portable x-ray source.	2.04	1	0	f-block element atom; lanthanoid atom
yttrium Yttrium: An element of the rare earth family of metals. It has the atomic symbol Y, atomic number 39, and atomic weight 88.91. In conjunction with other rare earths, yttrium is used as a phosphor in television receivers and is a component of the yttrium-aluminum garnet (YAG) lasers.	2.13	1	0	d-block element atom; rare earth metal atom; scandium group element atom
zirconium Zirconium: A rather rare metallic element with atomic number 40, atomic weight 91.224, and symbol Zr.	2.58	2	0	titanium group element atom
galactosamine 2-amino-2-deoxy-D-galactopyranose : The pyranose form of D-galactosamine.. D-galactosamine : The D-stereoisomer of galactosamine.	7.5	2	0	D-galactosamine; primary amino compound	toxin
hypochlorous acid Hypochlorous Acid: An oxyacid of chlorine (HClO) containing monovalent chlorine that acts as an oxidizing or reducing agent.. hypochlorous acid : A chlorine oxoacid with formula HOCl; a weak, unstable acid, it is the active form of chlorine in water.	2.46	2	0	chlorine oxoacid; reactive oxygen species	EC 2.5.1.18 (glutathione transferase) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; human metabolite
nickel chloride nickel chloride: RN given refers to cpd with MF of Ni-Cl2. nickel dichloride : A compound of nickel and chloride in which the ratio of nickel (in the +2 oxidation state) to chloride is 1:2.	1.99	1	0	nickel coordination entity	calcium channel blocker; hapten
ferrous sulfate ferrous sulfate: Ferro-Gradumet is ferrous sulfate in controlled release form; RN given refers to Fe(+2)[1:1] salt. iron(2+) sulfate (anhydrous) : A compound of iron and sulfate in which the ratio of iron(2+) to sulfate ions is 1:1. Various hydrates occur naturally - most commonly the heptahydrate, which loses water to form the tetrahydrate at 57degreeC and the monohydrate at 65degreeC.	4.7	6	1	iron molecular entity; metal sulfate	reducing agent
bromine Bromine: A halogen with the atomic symbol Br, atomic number 35, and atomic weight 79.904. It is a volatile reddish-brown liquid that gives off suffocating vapors, is corrosive to the skin, and may cause severe gastroenteritis if ingested.	1.95	1	0	diatomic bromine
barium sulfate Barium Sulfate: A compound used as an x-ray contrast medium that occurs in nature as the mineral barite. It is also used in various manufacturing applications and mixed into heavy concrete to serve as a radiation shield.. barium sulfate : A metal sulfate with formula BaO4S. Virtually insoluble in water at room temperature, it is mostly used as a component in oil well drilling fluid it occurs naturally as the mineral barite.	1.94	1	0	barium salt; inorganic barium salt; metal sulfate	radioopaque medium
s-methylcysteine S-methylcysteine: RN given refers to parent cpd without isomeric designation. S-methylcysteine : A cysteine derivative that is L-cysteine in which the hydrogen attached to the sulfur is replaced by a methyl group.	2.21	1	0	S-alkyl-L-cysteine zwitterion; S-alkyl-L-cysteine	human urinary metabolite; plant metabolite
zinc sulfate Zinc Sulfate: A compound given in the treatment of conditions associated with zinc deficiency such as acrodermatitis enteropathica. Externally, zinc sulfate is used as an astringent in lotions and eye drops. (Reynolds JEF(Ed): Martindale: The Extra Pharmacopoeia (electronic version). Micromedex, Inc, Englewood, CO, 1995). zinc sulfate : A metal sulfate compound having zinc(2+) as the counterion.	2.13	1	0	metal sulfate; zinc molecular entity	fertilizer
sodium sulfate [no description available]	2.41	1	0	inorganic sodium salt
sodium sulfite [no description available]	2.05	1	0	inorganic sodium salt; sulfite salt	food preservative; reducing agent
tricalcium phosphate tricalcium phosphate: a form of tricalcium phosphate used as bioceramic bone replacement material; see also records for alpha-tricalcium phosphate, beta-tricalcium phosphate, calcium phosphate; apatitic tricalcium phosphate Ca9(HPO4)(PO4)5(OH) is the calcium orthophosphate leading to beta tricalcium phosphate Ca3(PO4)2 (b-TCP). calcium phosphate : A calcium salt composed of calcium and phosphate/diphosphate ions; present in milk and used for the mineralisation of calcified tissues.	2.07	1	0	calcium phosphate
ferrous chloride ferrous chloride: induces convulsions; RN given refers to parent cpd	2.05	1	0	iron coordination entity
chromates Chromates: Salts of chromic acid containing the CrO(2-)4 radical.. chromate(2-) : A chromium oxoanion resulting from the removal of two protons from chromic acid.	1.94	1	0	chromium oxoanion; divalent inorganic anion	oxidising agent
copper sulfate Copper Sulfate: A sulfate salt of copper. It is a potent emetic and is used as an antidote for poisoning by phosphorus. It also can be used to prevent the growth of algae.. copper(II) sulfate : A metal sulfate compound having copper(2+) as the metal ion.	4.35	4	1	metal sulfate	emetic; fertilizer; sensitiser
calcium sulfate Calcium Sulfate: A calcium salt that is used for a variety of purposes including: building materials, as a desiccant, in dentistry as an impression material, cast, or die, and in medicine for immobilizing casts and as a tablet excipient. It exists in various forms and states of hydration. Plaster of Paris is a mixture of powdered and heat-treated gypsum.	2.06	1	0	calcium salt; inorganic calcium salt
potassium dichromate Potassium Dichromate: Chromic acid (H2Cr2O7), dipotassium salt. A compound having bright orange-red crystals and used in dyeing, staining, tanning leather, as bleach, oxidizer, depolarizer for dry cells, etc. Medically it has been used externally as an astringent, antiseptic, and caustic. When taken internally, it is a corrosive poison.. potassium dichromate : A potassium salt that is the dipotassium salt of dichromic acid.	2.13	1	0	potassium salt	allergen; oxidising agent; sensitiser
fluorine Fluorine: A nonmetallic, diatomic gas that is a trace element and member of the halogen family. It is used in dentistry as fluoride (FLUORIDES) to prevent dental caries.	2.21	1	0	diatomic fluorine; gas molecular entity	NMR chemical shift reference compound
chlorine Chlorine: An element with atomic symbol Cl, atomic number 17, and atomic weight 35, and member of the halogen family.	2.03	1	0	diatomic chlorine; gas molecular entity	bleaching agent
deuterium oxide Deuterium Oxide: The isotopic compound of hydrogen of mass 2 (deuterium) with oxygen. (From Grant & Hackh's Chemical Dictionary, 5th ed) It is used to study mechanisms and rates of chemical or nuclear reactions, as well as biological processes.	2.41	1	0	deuterated compound; water	NMR solvent
butylated hydroxyanisole [no description available]	3.79	3	0
galactose aldohexose : A hexose with a (potential) aldehyde group at one end.	5.57	22	0
ozone Ozone: The unstable triatomic form of oxygen, O3. It is a powerful oxidant that is produced for various chemical and industrial uses. Its production is also catalyzed in the ATMOSPHERE by ULTRAVIOLET RAY irradiation of oxygen or other ozone precursors such as VOLATILE ORGANIC COMPOUNDS and NITROGEN OXIDES. About 90% of the ozone in the atmosphere exists in the stratosphere (STRATOSPHERIC OZONE).. ozone : An elemental molecule with formula O3. An explosive, pale blue gas (b.p. -112degreeC) that has a characteristic, pungent odour, it is continuously produced in the upper atmosphere by the action of solar ultraviolet radiation on atmospheric oxygen. It is an antimicrobial agent used in the production of bottled water, as well as in the treatment of meat, poultry and other foodstuffs.	7.96	4	0	elemental molecule; gas molecular entity; reactive oxygen species; triatomic oxygen	antiseptic drug; disinfectant; electrophilic reagent; greenhouse gas; mutagen; oxidising agent; tracer
ferric sulfate ferric sulfate: RN given refers to Fe(+3)[3:2] salt). iron(3+) sulfate : A compound of iron and sulfate in which the ratio of iron(3+) to sulfate ions is 3:2.	2.46	2	0	iron molecular entity; metal sulfate	astringent; catalyst; mordant
aluminum sulfate aluminium sulfate (anhydrous) : An aluminium sulfate that contains no water of crystallisation.	2.39	2	0	aluminium sulfate
lead nitrate lead nitrate: RN given refers to unspecified lead nitrate	2.06	1	0	inorganic nitrate salt; lead coordination entity
barium chloride barium chloride: RN given refers to parent cpd. barium chloride : The inorganic dichloride salt of barium.	1.96	1	0	barium salt; inorganic chloride	potassium channel blocker
trolamine salicylate Arthritis: Acute or chronic inflammation of JOINTS.	2.1	1	0
ammonium chloride Ammonium Chloride: An acidifying agent that has expectorant and diuretic effects. Also used in etching and batteries and as a flux in electroplating.. ammonium chloride : An inorganic chloride having ammonium as the counterion.	2.38	2	0	ammonium salt; inorganic chloride	ferroptosis inhibitor
3-hydroxybenzo(a)pyrene 3-hydroxybenzo(a)pyrene: RN given refers to unlabeled parent cpd	3.1	1	0	ortho- and peri-fused polycyclic arene
titanium dioxide titanium dioxide: used medically as protectant against externally caused irritation & sunlight; high concentrations of dust may cause irritation to respiratory tract; RN given refers to titanium oxide (TiO2); structure. titanium dioxide : A titanium oxide with the formula TiO2. A naturally occurring oxide sourced from ilmenite, rutile and anatase, it has a wide range of applications.	3.32	6	0	titanium oxides	food colouring
tiletamine hydrochloride Cyclohexanones: Cyclohexane ring substituted by one or more ketones in any position.. cyclohexanones : Any alicyclic ketone based on a cyclohexane skeleton and its substituted derivatives thereof.	2.73	3	0
selegiline Selegiline: A selective, irreversible inhibitor of Type B monoamine oxidase that is used for the treatment of newly diagnosed patients with PARKINSON DISEASE, and for the treatment of depressive disorders. The compound without isomeric designation is Deprenyl.	2.1	1	0	selegiline; terminal acetylenic compound	geroprotector
levamisole Levamisole: An antihelminthic drug that has been tried experimentally in rheumatic disorders where it apparently restores the immune response by increasing macrophage chemotaxis and T-lymphocyte function. Paradoxically, this immune enhancement appears to be beneficial in rheumatoid arthritis where dermatitis, leukopenia, and thrombocytopenia, and nausea and vomiting have been reported as side effects. (From Smith and Reynard, Textbook of Pharmacology, 1991, p435-6). levamisole : A 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole that has S configuration. It is used (generally as the monohydrochloride salt) to treat parasitic worm infections in pigs, sheep and cattle and was formerly used in humans as an adjuvant to chemotherapy for the treatment of various cancers. It is also widely used as an adulterant to coccaine.	4.15	3	1	6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole	antinematodal drug; antirheumatic drug; EC 3.1.3.1 (alkaline phosphatase) inhibitor; immunological adjuvant; immunomodulator
4-n-Pentylphenol [no description available]	3.1	1	0	phenols
cephalexin Cephalexin: A semisynthetic cephalosporin antibiotic with antimicrobial activity similar to that of CEPHALORIDINE or CEPHALOTHIN, but somewhat less potent. It is effective against both gram-positive and gram-negative organisms.. cephalexin : A semisynthetic first-generation cephalosporin antibiotic having methyl and beta-(2R)-2-amino-2-phenylacetamido groups at the 3- and 7- of the cephem skeleton, respectively. It is effective against both Gram-negative and Gram-positive organisms, and is used for treatment of infections of the skin, respiratory tract and urinary tract.	2.1	1	0	beta-lactam antibiotic allergen; cephalosporin; semisynthetic derivative	antibacterial drug
cromolyn sodium Cromolyn Sodium: A chromone complex that acts by inhibiting the release of chemical mediators from sensitized MAST CELLS. It is used in the prophylactic treatment of both allergic and exercise-induced asthma, but does not affect an established asthmatic attack.. disodium cromoglycate : An organic sodium salt that is the disodium salt of cromoglycic acid.	2.49	2	0	organic sodium salt	anti-asthmatic drug; drug allergen
ferric nitrilotriacetate ferric nitrilotriacetate: induces diabetes in animals (iron loading)	2.03	1	0	iron chelate	carcinogenic agent; mutagen
tetradecanoylphorbol acetate Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.	5.6	74	0	acetate ester; diester; phorbol ester; tertiary alpha-hydroxy ketone; tetradecanoate ester	antineoplastic agent; apoptosis inducer; carcinogenic agent; mitogen; plant metabolite; protein kinase C agonist; reactive oxygen species generator
2,3-dihydroxypyridine 2,3-dihydroxypyridine: affects thyroid function. pyridine-2,3-diol : A dihydroxypyridine in which the two hydroxy groups are located at positions 2 and 3.	2.04	1	0	dihydroxypyridine
fluorides [no description available]	2.94	4	0	halide anion; monoatomic fluorine
9-hydroxybenzo(a)pyrene 9-hydroxybenzo(a)pyrene: RN given refers to unlabeled parent cpd	3.1	1	0	ortho- and peri-fused polycyclic arene
chromium chromium hexavalent ion: a human respiratory carcinogen	2.88	3	0	chromium cation; monoatomic hexacation
keracyanin cyanidin 3-rutinoside: an anthocyanin compound. cyanidin 3-O-rutinoside chloride : A member of the class of anthocyanin chlorides that has cyanidin 3-O-rutinoside as the cationic counterpart.	2.08	1	0	anthocyanin chlorides
iodine [no description available]	2.69	3	0	halide anion; monoatomic iodine	human metabolite
osmium tetroxide Osmium Tetroxide: (T-4)-Osmium oxide (OsO4). A highly toxic and volatile oxide of osmium used in industry as an oxidizing agent. It is also used as a histological fixative and stain and as a synovectomy agent in arthritic joints. Its vapor can cause eye, skin, and lung damage.. osmium tetroxide : An osmium coordination entity consisting of four oxygen atoms bound to a central osmium atom via covalent double bonds.	2.67	3	0	osmium coordination entity	fixative; histological dye; oxidising agent; poison
daunorubicin Daunorubicin: A very toxic anthracycline aminoglycoside antineoplastic isolated from Streptomyces peucetius and others, used in treatment of LEUKEMIA and other NEOPLASMS.. anthracycline : Anthracyclines are polyketides that have a tetrahydronaphthacenedione ring structure attached by a glycosidic linkage to the amino sugar daunosamine.. daunorubicin : A natural product found in Actinomadura roseola.	3.51	2	0	aminoglycoside antibiotic; anthracycline; p-quinones; tetracenequinones	antineoplastic agent; bacterial metabolite
razoxane Razoxane: An antimitotic agent with immunosuppressive properties.	1.96	1	0	N-alkylpiperazine
zingerone zingerone: pungent principle of ginger; structure. zingerone : A methyl ketone that is 4-phenylbutan-2-one in which the phenyl ring is substituted at positions 3 and 4 by methoxy and hydroxy groups respectively. The major pungent component in ginger.	2.21	1	0	methyl ketone; monomethoxybenzene; phenols	anti-inflammatory agent; antiemetic; antioxidant; flavouring agent; fragrance; plant metabolite; radiation protective agent
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	4.5	23	0	benzenes; phenyl acetates
n-phenylethanolamine [no description available]	3.1	1	0	aralkylamine
phenoxyethanol phenoxyethanol: structure. 2-phenoxyethanol : An aromatic ether that is phenol substituted on oxygen by a 2-hydroxyethyl group.	2.05	1	0	aromatic ether; glycol ether; primary alcohol	antiinfective agent; central nervous system depressant
4-ethylphenol 4-ethylphenol: RN given refers to parent cpd. 4-ethylphenol : A member of the class of phenols carrying an ethyl substituent at position 4.	3.84	3	0	phenols	fungal xenobiotic metabolite
4-anisaldehyde 4-anisaldehyde: RN given refers to cpd with specified locants for methoxy moieties; structure in Merck, 9th ed, #696. p-methoxybenzaldehyde : A member of the class of benzaldehydes consisting of benzaldehyde itself carrying a methoxy substituent at position 4.	2.55	2	0	benzaldehydes	bacterial metabolite; human urinary metabolite; insect repellent; plant metabolite
myrcene myrcene: structure in first source. beta-myrcene : A monoterpene that is octa-1,6-diene bearing methylene and methyl substituents at positions 3 and 7 respectively.	2.05	1	0	monoterpene	anabolic agent; anti-inflammatory agent; flavouring agent; fragrance; plant metabolite; volatile oil component
isopentyl alcohol isopentyl alcohol: RN given refers to unlabeled parent cpd. isoamylol : An primary alcohol that is butan-1-ol in which a hydrogen at position 3 has been replaced by a methyl group.	2.15	1	0	alkyl alcohol; primary alcohol; volatile organic compound	antifungal agent; Saccharomyces cerevisiae metabolite; xenobiotic metabolite
pyrrolidine [no description available]	2.1	1	0	azacycloalkane; pyrrolidines; saturated organic heteromonocyclic parent
1,4-dioxane 1,4-dioxane: dehydrating agent; polar solvent miscible both with water & most organic solvents. dioxane : Any member of the class of dioxanes that is a cyclohexane in which two carbon atoms are replaced by oxygen atoms.. 1,4-dioxane : A dioxane with oxygen atoms at positions 1 and 4.	2.25	1	0	dioxane; volatile organic compound	carcinogenic agent; metabolite; NMR chemical shift reference compound; non-polar solvent
ursodeoxycholic acid Ursodeoxycholic Acid: An epimer of chenodeoxycholic acid. It is a mammalian bile acid found first in the bear and is apparently either a precursor or a product of chenodeoxycholate. Its administration changes the composition of bile and may dissolve gallstones. It is used as a cholagogue and choleretic.. ursodeoxycholic acid : A bile acid found in the bile of bears (Ursidae) as a conjugate with taurine. Used therapeutically, it prevents the synthesis and absorption of cholesterol and can lead to the dissolution of gallstones.. ursodeoxycholate : A bile acid anion that is the conjugate base of ursodeoxycholic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.	3.1	1	0	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
pregnanolone Pregnanolone: A pregnane found in the urine of pregnant women and sows. It has anesthetic, hypnotic, and sedative properties.. 3alpha-hydroxy-5beta-pregnan-20-one : The 3alpha-stereoisomer of 3-hydroxy-5beta-pregnan-20-one.	3.1	1	0	3-hydroxy-5beta-pregnan-20-one; 3alpha-hydroxy steroid	human metabolite; intravenous anaesthetic; sedative
butylated hydroxytoluene 2,6-di-tert-butyl-4-methylphenol : A member of the class of phenols that is 4-methylphenol substituted by tert-butyl groups at positions 2 and 6.	5.25	6	0	phenols	antioxidant; ferroptosis inhibitor; food additive; geroprotector
pyrene pyrene: structure in Merck Index, 9th ed, #7746. pyrene : An ortho- and peri-fused polycyclic arene consisting of four fused benzene rings, resulting in a flat aromatic system.	2.59	2	0	ortho- and peri-fused polycyclic arene	fluorescent probe; persistent organic pollutant
metipranolol Metipranolol: A beta-adrenergic antagonist effective for both beta-1 and beta-2 receptors. It is used as an antiarrhythmic, antihypertensive, and antiglaucoma agent.. metipranolol : 3-(Propan-2-ylamino)propane-1,2-diol in which the hydrogen of the primary hydroxy group is substituted by a 4-acetoxy-2,3,5-trimethylphenoxy group. A non-cardioselective beta-blocker, it is used to lower intra-ocular pressure in the management of open-angle glaucoma.	2.1	1	0	acetate ester; aromatic ether; propanolamine; secondary amino compound	anti-arrhythmia drug; antiglaucoma drug; antihypertensive agent; beta-adrenergic antagonist
8-bromo cyclic adenosine monophosphate 8-Bromo Cyclic Adenosine Monophosphate: A long-acting derivative of cyclic AMP. It is an activator of cyclic AMP-dependent protein kinase, but resistant to degradation by cyclic AMP phosphodiesterase.. 8-Br-cAMP : A 3',5'-cyclic purine nucleotide that is 3',5'-cyclic AMP bearing an additional bromo substituent at position 8 on the adenine ring. An activator of cyclic AMP-dependent protein kinase, but resistant to degradation by cyclic AMP phosphodiesterase.	3.48	8	0	3',5'-cyclic purine nucleotide; adenyl ribonucleotide; organobromine compound	antidepressant; protein kinase agonist
transferrin Transferrin: An iron-binding beta1-globulin that is synthesized in the LIVER and secreted into the blood. It plays a central role in the transport of IRON throughout the circulation. A variety of transferrin isoforms exist in humans, including some that are considered markers for specific disease states.	2.66	2	0
propamocarb propamocarb: RN given refers to parent cpd. propamocarb : A carbamate ester that is the propyl ester of 3-(dimethylamino)propylcarbamic acid. It is a systemic fungicide, used (normally as the hydrochloride salt) for the control of soil, root and leaf diseases caused by oomycetes, particularly Phytophthora and Pythium species.	2.1	1	0	carbamate ester; carbamate fungicide; tertiary amino compound	antifungal agrochemical; environmental contaminant; xenobiotic
aluminum oxide hydroxide aluminum oxide hydroxide: RN given refers to Al2O3.xH2O	2.53	2	0	aluminium hydroxides; aluminium oxides
alkenes [no description available]	2.99	4	0
calcium oxalate Calcium Oxalate: The calcium salt of oxalic acid, occurring in the urine as crystals and in certain calculi.. calcium oxalate : The calcium salt of oxalic acid, which in excess in the urine may lead to formation of oxalate calculi (kidney stones).	3.17	4	0	organic calcium salt
glutamic acid Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.	3.82	11	0	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
torpedo Torpedo: A genus of the Torpedinidae family consisting of several species. Members of this family have powerful electric organs and are commonly called electric rays.	2	1	0
sodium azide Sodium Azide: A cytochrome oxidase inhibitor which is a nitridizing agent and an inhibitor of terminal oxidation. (From Merck Index, 12th ed). sodium azide : The sodium salt of hydrogen azide (hydrazoic acid).	1.97	1	0	inorganic sodium salt	antibacterial agent; explosive; mitochondrial respiratory-chain inhibitor; mutagen
azides Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.	2.69	3	0	pseudohalide anion	mitochondrial respiratory-chain inhibitor
adenosine diphosphate ribose Adenosine Diphosphate Ribose: An ester formed between the aldehydic carbon of RIBOSE and the terminal phosphate of ADENOSINE DIPHOSPHATE. It is produced by the hydrolysis of nicotinamide-adenine dinucleotide (NAD) by a variety of enzymes, some of which transfer an ADP-ribosyl group to target proteins.	2.69	3	0	ADP-sugar	Escherichia coli metabolite; mouse metabolite
amoxicillin Amoxicillin: A broad-spectrum semisynthetic antibiotic similar to AMPICILLIN except that its resistance to gastric acid permits higher serum levels with oral administration.. amoxicillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-(4-hydroxyphenyl)acetamido group.	2.1	1	0	penicillin allergen; penicillin	antibacterial drug
timolol (S)-timolol (anhydrous) : The (S)-(-) (more active) enantiomer of timolol. A beta-adrenergic antagonist, both the hemihydrate and the maleate salt are used in the mangement of glaucoma, hypertension, angina pectoris and myocardial infarction, and for the prevention of migraine.	2.1	1	0	timolol	anti-arrhythmia drug; antiglaucoma drug; antihypertensive agent; beta-adrenergic antagonist
norflurazone norflurazone: structure. norflurazon : A pyridazinone that is pyridazin-3(2H)-one which is substituted at positions 2, 4, and 5 by m-(trifluoromethyl)phenyl, chloro, and methylamino groups, respectively. A pre-emergence herbicide used to control grasses and broad-leafed weeds in a variety of crops. Not approved for use within the European Union.	2.05	1	0	(trifluoromethyl)benzenes; organochlorine compound; pyridazinone; secondary amino compound	agrochemical; carotenoid biosynthesis inhibitor; herbicide
ferrozine Ferrozine: A ferroin compound that forms a stable magenta-colored solution with the ferrous ion. The complex has an absorption peak at 562 nm and is used as a reagent and indicator for iron.	2.05	1	0
nigericin Nigericin: A polyether antibiotic which affects ion transport and ATPase activity in mitochondria. It is produced by Streptomyces hygroscopicus. (From Merck Index, 11th ed). nigericin : A polyether antibiotic which affects ion transport and ATPase activity in mitochondria. It is produced by Streptomyces hygroscopicus.	1.97	1	0	polycyclic ether	antibacterial agent; antimicrobial agent; bacterial metabolite; potassium ionophore
zidovudine Zidovudine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.. zidovudine : A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.	3.49	2	0	azide; pyrimidine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; HIV-1 reverse transcriptase inhibitor
tobramycin Tobramycin: An aminoglycoside, broad-spectrum antibiotic produced by Streptomyces tenebrarius. It is effective against gram-negative bacteria, especially the PSEUDOMONAS species. It is a 10% component of the antibiotic complex, NEBRAMYCIN, produced by the same species.. tobramycin : A amino cyclitol glycoside that is kanamycin B lacking the 3-hydroxy substituent from the 2,6-diaminoglucose ring.	7.31	1	0	amino cyclitol glycoside	antibacterial agent; antimicrobial agent; toxin
paclitaxel Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).	3.26	5	0	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
etoposide [no description available]	1.97	1	0	beta-D-glucoside; furonaphthodioxole; organic heterotetracyclic compound	antineoplastic agent; DNA synthesis inhibitor
substance p [no description available]	2.39	2	0	peptide	neurokinin-1 receptor agonist; neurotransmitter; vasodilator agent
6-hydroxybenzo(a)pyrene 6-hydroxybenzo(a)pyrene: RN given refers to parent cpd; structure in first source	3.1	1	0	ortho- and peri-fused polycyclic arene
7-hydroxytropolone 7-hydroxytropolone: structure	2.17	1	0
phenyl-2-aminoethyl sulfide phenyl-2-aminoethyl sulfide: dopamine-beta-hydroxylase substrate; structure given in first source	2.1	1	0
enilconazole enilconazole: RN given refers to parent cpd. enilconazole : A racemate comprising equimolar amounts of (R)- and (S)-enilconazole. A fungicide used to control a wide range of fungi including Tilletia and Helminthosporium spp. on fruit, vegetables and ornamentals. In veterinary medicine, it is used topically for the treatment of fungal skin infections in cattle, dogs, and horses; it is also used by inhalation for the treatment of aspergillosis in ostriches.. 1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole : A member of the class of imidazoles in which the hydrogen at position 1 is replaced by a 2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl group.	2.21	1	0	dichlorobenzene; ether; imidazoles
ribavirin Rebetron: Rebetron is tradename	2.05	1	0	1-ribosyltriazole; aromatic amide; monocarboxylic acid amide; primary carboxamide	anticoronaviral agent; antiinfective agent; antimetabolite; antiviral agent; EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
lentinan [no description available]	2.17	1	0
amikacin Amikacin: A broad-spectrum antibiotic derived from KANAMYCIN. It is reno- and oto-toxic like the other aminoglycoside antibiotics.. amikacin : An amino cyclitol glycoside that is kanamycin A acylated at the N-1 position by a 4-amino-2-hydroxybutyryl group.	2.03	1	0	alpha-D-glucoside; amino cyclitol glycoside; aminoglycoside; carboxamide	antibacterial drug; antimicrobial agent; nephrotoxin
phorbol 12,13-dibutyrate Phorbol 12,13-Dibutyrate: A phorbol ester found in CROTON OIL which, in addition to being a potent skin tumor promoter, is also an effective activator of calcium-activated, phospholipid-dependent protein kinase (protein kinase C). Due to its activation of this enzyme, phorbol 12,13-dibutyrate profoundly affects many different biological systems.	2.4	2	0	butyrate ester; phorbol ester; tertiary alpha-hydroxy ketone
tolamolol [no description available]	2.1	1	0
methyldopa Methyldopa: An alpha-2 adrenergic agonist that has both central and peripheral nervous system effects. Its primary clinical use is as an antihypertensive agent.. alpha-methyl-L-dopa : A derivative of L-tyrosine having a methyl group at the alpha-position and an additional hydroxy group at the 3-position on the phenyl ring.	2.38	2	0	L-tyrosine derivative; non-proteinogenic L-alpha-amino acid	alpha-adrenergic agonist; antihypertensive agent; hapten; peripheral nervous system drug; sympatholytic agent
sq-11725 Nadolol: A non-selective beta-adrenergic antagonist with a long half-life, used in cardiovascular disease to treat arrhythmias, angina pectoris, and hypertension. Nadolol is also used for MIGRAINE DISORDERS and for tremor.. nadolol : Nadolol is a diastereoisomeric mixture consisting of equimolar amounts of the four possible 2,3-cis-isomers of 5-[3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydronaphthalene-2,3-diol.	2.1	1	0
diltiazem Diltiazem: A benzothiazepine derivative with vasodilating action due to its antagonism of the actions of CALCIUM ion on membrane functions.. diltiazem : A 5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate in which both stereocentres have S configuration. A calcium-channel blocker and vasodilator, it is used as the hydrochloride in the management of angina pectoris and hypertension.	9.28	19	0	5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate	antihypertensive agent; calcium channel blocker; vasodilator agent
ng-nitroarginine methyl ester NG-Nitroarginine Methyl Ester: A non-selective inhibitor of nitric oxide synthase. It has been used experimentally to induce hypertension.	3.3	6	0	alpha-amino acid ester; L-arginine derivative; methyl ester; N-nitro compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor
dexibuprofen dexibuprofen: structure in first source	3.1	1	0	ibuprofen	non-narcotic analgesic; non-steroidal anti-inflammatory drug
benoxaprofen benoxaprofen: RN given refers to parent cpd; structure. benoxaprofen : A monocarboxylic acid that is propionic acid substituted at position 2 by a 2-(4-chlorophenyl)-1,3-benzoxazol-5-yl group. It was used as a non-steroidal anti-inflammatory drug until 1982 when it was withdrawn from the market due to adverse side-effects including liver necrosis, photosensitivity, and carcinogenicity in animals.	3.1	1	0	1,3-benzoxazoles; monocarboxylic acid; monochlorobenzenes	antipsoriatic; antipyretic; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; hepatotoxic agent; nephrotoxin; non-narcotic analgesic; non-steroidal anti-inflammatory drug; protein kinase C agonist
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid [no description available]	6.21	41	0	chromanol; monocarboxylic acid; phenols	antioxidant; ferroptosis inhibitor; neuroprotective agent; radical scavenger; Wnt signalling inhibitor
3,3',5,5'-tetramethylbenzidine T1023: radioprotective NO-Synthase Inhibitor	3.14	5	0
sufentanil Sufentanil: An opioid analgesic that is used as an adjunct in anesthesia, in balanced anesthesia, and as a primary anesthetic agent.. sufentanil : An anilide resulting from the formal condensation of the aryl amino group of 4-(methoxymethyl)-N-phenyl-1-[2-(2-thienyl)ethyl]piperidin-4-amine with propanoic acid.	2.1	1	0	anilide; ether; piperidines; thiophenes	anaesthesia adjuvant; intravenous anaesthetic; mu-opioid receptor agonist; opioid analgesic
acarbose [no description available]	2.82	2	0	tetrasaccharide derivative	EC 3.2.1.1 (alpha-amylase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; geroprotector; hypoglycemic agent
2-hydroxybenzo(a)pyrene 2-hydroxybenzo(a)pyrene: RN given refers to parent cpd; structure in first source	3.1	1	0	ortho- and peri-fused polycyclic arene
indacrinone indacrinone: polyvalent saluretic; RN given refers to parent cpd without isomeric designation; structure	2.13	1	0
Flamprop [no description available]	2.1	1	0	benzamides
clorsulon clorsulon: potent fasciolicide; structure	1.98	1	0	benzenes; sulfonamide
piperacillin Piperacillin: Semisynthetic, broad-spectrum, AMPICILLIN derived ureidopenicillin antibiotic proposed for PSEUDOMONAS infections. It is also used in combination with other antibiotics.. piperacillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-[(4-ethyl-2,3-dioxopiperazin-1-yl)carboxamido]-2-phenylacetamido group.	2.05	1	0	penicillin allergen; penicillin	antibacterial drug
paroxetine Paroxetine: A serotonin uptake inhibitor that is effective in the treatment of depression.. paroxetine : A benzodioxole that consists of piperidine bearing 1,3-benzodioxol-5-yloxy)methyl and 4-fluorophenyl substituents at positions 3 and 4 respectively; the (3S,4R)-diastereomer. Highly potent and selective 5-HT uptake inhibitor that binds with high affinity to the serotonin transporter (Ki = 0.05 nM). Ki values are 1.1, 350 and 1100 nM for inhibition of [3H]-5-HT, [3H]-l-NA and [3H]-DA uptake respectively. Displays minimal affinity for alpha1-, alpha2- or beta-adrenoceptors, 5-HT2A, 5-HT1A, D2 or H1 receptors at concentrations below 1000 nM, however displays weak affinity for muscarinic ACh receptors (Ki = 42 nM). Antidepressant and anxiolytic in vivo.	2.1	1	0	aromatic ether; benzodioxoles; organofluorine compound; piperidines	antidepressant; anxiolytic drug; hepatotoxic agent; P450 inhibitor; serotonin uptake inhibitor
captopril Captopril: A potent and specific inhibitor of PEPTIDYL-DIPEPTIDASE A. It blocks the conversion of ANGIOTENSIN I to ANGIOTENSIN II, a vasoconstrictor and important regulator of arterial blood pressure. Captopril acts to suppress the RENIN-ANGIOTENSIN SYSTEM and inhibits pressure responses to exogenous angiotensin.. captopril : A L-proline derivative in which L-proline is substituted on nitrogen with a (2S)-2-methyl-3-sulfanylpropanoyl group. It is used as an anti-hypertensive ACE inhibitor drug.	2.01	1	0	alkanethiol; L-proline derivative; N-acylpyrrolidine; pyrrolidinemonocarboxylic acid	antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor
bw-755c 4,5-Dihydro-1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-3-amine: A dual inhibitor of both cyclooxygenase and lipoxygenase pathways. It exerts an anti-inflammatory effect by inhibiting the formation of prostaglandins and leukotrienes. The drug also enhances pulmonary hypoxic vasoconstriction and has a protective effect after myocardial ischemia.	1.97	1	0
colforsin Colforsin: Potent activator of the adenylate cyclase system and the biosynthesis of cyclic AMP. From the plant COLEUS FORSKOHLII. Has antihypertensive, positive inotropic, platelet aggregation inhibitory, and smooth muscle relaxant activities; also lowers intraocular pressure and promotes release of hormones from the pituitary gland.	4.23	18	0	acetate ester; cyclic ketone; labdane diterpenoid; organic heterotricyclic compound; tertiary alpha-hydroxy ketone; triol	adenylate cyclase agonist; anti-HIV agent; antihypertensive agent; plant metabolite; platelet aggregation inhibitor; protein kinase A agonist
2-amino-6-methyldipyrido(1,2-a-3',2'-d)imidazole 2-amino-6-methyldipyrido(1,2-a-3',2'-d)imidazole: structure	1.97	1	0	imidazopyridine
sulotroban sulotroban: thromboxane receptor antagonist	2	1	0
lovastatin Lovastatin: A fungal metabolite isolated from cultures of Aspergillus terreus. The compound is a potent anticholesteremic agent. It inhibits 3-hydroxy-3-methylglutaryl coenzyme A reductase (HYDROXYMETHYLGLUTARYL COA REDUCTASES), which is the rate-limiting enzyme in cholesterol biosynthesis. It also stimulates the production of low-density lipoprotein receptors in the liver.. lovastatin : A fatty acid ester that is mevastatin carrying an additional methyl group on the carbobicyclic skeleton. It is used in as an anticholesteremic drug and has been found in fungal species such as Aspergillus terreus and Pleurotus ostreatus (oyster mushroom).	7.02	1	0	delta-lactone; fatty acid ester; hexahydronaphthalenes; polyketide; statin (naturally occurring)	anticholesteremic drug; antineoplastic agent; Aspergillus metabolite; prodrug
remoxipride Remoxipride: An antipsychotic agent that is specific for dopamine D2 receptors. It has been shown to be effective in the treatment of schizophrenia.	2.42	2	0	dimethoxybenzene
quinpirole Quinpirole: A dopamine D2/D3 receptor agonist.. quinpirole : A pyrazoloquinoline that is (4aR,8aR)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrazolo[3,4-g]quinoline substituted by a propyl group at position 5. It acts as a dopamine agonist.	1.98	1	0	pyrazoloquinoline	dopamine agonist
atomoxetine atomoxetine : A secondary amino compound having methyl and 3-(2-methylphenoxy)-3-phenylpropan-1-yl substituents.	2.1	1	0	aromatic ether; secondary amino compound; toluenes	adrenergic uptake inhibitor; antidepressant; environmental contaminant; xenobiotic
ilmofosine ilmofosine: used in treatment of colonic adenocarcinoma in rats; structure given in first source; RN given refers to hydroxide inner salt	1.99	1	0
mifepristone Mifepristone: A progestational and glucocorticoid hormone antagonist. Its inhibition of progesterone induces bleeding during the luteal phase and in early pregnancy by releasing endogenous prostaglandins from the endometrium or decidua. As a glucocorticoid receptor antagonist, the drug has been used to treat hypercortisolism in patients with nonpituitary CUSHING SYNDROME.	2.7	3	0	3-oxo-Delta(4) steroid; acetylenic compound; tertiary amino compound	abortifacient; contraceptive drug; hormone antagonist; synthetic oral contraceptive
fura-2 Fura-2: A fluorescent calcium chelating agent which is used to study intracellular calcium in tissues.	4.23	18	0
eticlopride eticlopride: blocks dopamine-D2 binding sites; structure given in first source; RN given refers to (S)-isomer	2.01	1	0	salicylamides
imiquimod Imiquimod: A topically-applied aminoquinoline immune modulator that induces interferon production. It is used in the treatment of external genital and perianal warts, superficial CARCINOMA, BASAL CELL; and ACTINIC KERATOSIS.. imiquimod : An imidazoquinoline fused [4,5-c] carrying isobutyl and amino substituents at N-1 and C-4 respectively. A prescription medication, it acts as an immune response modifier and is used to treat genital warts, superficial basal cell carcinoma, and actinic keratosis.	7.6	1	0	imidazoquinoline	antineoplastic agent; interferon inducer
n-(8-aminohexyl)-5-iodonaphthalene-1-sulfonamide N-(8-aminohexyl)-5-iodonaphthalene-1-sulfonamide: calmodulin antagonist	1.97	1	0
marbofloxacin [no description available]	2.61	2	0	quinolines
mibefradil Mibefradil: A benzimidazoyl-substituted tetraline that selectively binds and inhibits CALCIUM CHANNELS, T-TYPE.	2.4	2	0	tetralins	T-type calcium channel blocker
gemcitabine gemcitabine : A 2'-deoxycytidine having geminal fluoro substituents in the 2'-position. An inhibitor of ribonucleotide reductase, gemcitabine is used in the treatment of various carcinomas, particularly non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer.	2.06	1	0	organofluorine compound; pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent; antiviral drug; DNA synthesis inhibitor; EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor; environmental contaminant; immunosuppressive agent; photosensitizing agent; prodrug; radiosensitizing agent; xenobiotic
atorvastatin [no description available]	2.5	2	0	aromatic amide; dihydroxy monocarboxylic acid; monofluorobenzenes; pyrroles; statin (synthetic)	environmental contaminant; xenobiotic
irinotecan [no description available]	2.1	1	0	carbamate ester; delta-lactone; N-acylpiperidine; pyranoindolizinoquinoline; ring assembly; tertiary alcohol; tertiary amino compound	antineoplastic agent; apoptosis inducer; EC 5.99.1.2 (DNA topoisomerase) inhibitor; prodrug
zanamivir Zanamivir: A guanido-neuraminic acid that is used to inhibit NEURAMINIDASE.	2.1	1	0	guanidines	antiviral agent; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor
adenosine quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit	3.59	9	0	adenosines; purines D-ribonucleoside	analgesic; anti-arrhythmia drug; fundamental metabolite; human metabolite; vasodilator agent
octyl gallate [no description available]	12.86	95	0	gallate ester	food antioxidant; hypoglycemic agent; plant metabolite
pyranine pyranine: structure	2.08	1	0	organic sodium salt	fluorochrome
d-lactic acid (R)-lactic acid : An optically active form of lactic acid having (R)-configuration.	2.1	1	0	2-hydroxypropanoic acid	Escherichia coli metabolite; human metabolite
vanadates Vanadates: Oxyvanadium ions in various states of oxidation. They act primarily as ion transport inhibitors due to their inhibition of Na(+)-, K(+)-, and Ca(+)-ATPase transport systems. They also have insulin-like action, positive inotropic action on cardiac ventricular muscle, and other metabolic effects.. vanadate(3-) : A vanadium oxoanion that is a trianion with formula VO4 in which the vanadium is in the +5 oxidation state and is attached to four oxygen atoms.	2.67	3	0	trivalent inorganic anion; vanadium oxoanion	EC 3.1.3.1 (alkaline phosphatase) inhibitor; EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; EC 3.1.3.41 (4-nitrophenylphosphatase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor
1,2-dibromo-2,4-dicyanobutane 1,2-dibromo-2,4-dicyanobutane: biocide used in glue implicated in contact dermatitis; euxyl K 400 is a 2-phenoxyethanol mixture. 2-bromo-2-(bromomethyl)pentanedinitrile : An organobromine compound that consists of pentanedinitrile bearing bromo and bromomethyl substituents at position 2.	2.1	1	0	aliphatic nitrile; organobromine compound	allergen; sensitiser
2-amino-3,8-dimethylimidazo(4,5-f)quinoxaline 2-amino-3,8-dimethylimidazo(4,5-f)quinoxaline: strong mutagen found in broiled foods; structure given in first source. MeIQx : An imidazoquinoxaline that is 3H-imidazo[4,5-f]quinoxaline substituted at positions 3 and 8 by methyl groups and at position 2 by an amino group. A mutagenic compound found in cooked beef.	1.98	1	0	aromatic amine; imidazoquinoxaline	carcinogenic agent; genotoxin; Maillard reaction product; mutagen
vanillyl alcohol vanillyl alcohol: structure. vanillyl alcohol : A monomethoxybenzene that is 2-methoxyphenol substituted by a hydroxymethyl group at position 4.	2.44	2	0	benzyl alcohols; guaiacols	plant metabolite
2-methyl-5-(1-methylethyl)bicyclo(3.1.0)hexan-2-ol 2-methyl-5-(1-methylethyl)bicyclo(3.1.0)hexan-2-ol: fragrance ingredient; structure in first source	2.13	1	0	p-menthane monoterpenoid
benzylaminopurine benzylaminopurine: a plant growth regulator. N-benzyladenine : A member of the class of 6-aminopurines that is adenine in which one of the hydrogens of the amino group is replaced by a benzyl group.	2.08	1	0	6-aminopurines	cytokinin; plant metabolite
4-ethylguaiacol 4-ethylguaiacol: a constituent of wood creosote; suppresses intestinal smooth muscle contraction	2.11	1	0	methoxybenzenes; phenols
caloreen caloreen: glucose polymer with average length of five glucose units for dietary energy supplement. dextrin : Glucans produced by the hydrolysis of starch or glycogen. They are mixtures of polymers of D-glucose units linked by alpha(1->4) or alpha(1->6) glycosidic bonds.	2.07	1	0
2-amino-9h-pyrido(2,3-b)indole 2-amino-9H-pyrido(2,3-b)indole: pyrolysis product of soybean globulins; RN given refers to unlabeled cpd; structure	1.97	1	0	pyridoindole
venlafaxine hydrochloride Venlafaxine Hydrochloride: A cyclohexanol and phenylethylamine derivative that functions as a SEROTONIN AND NORADRENALINE REUPTAKE INHIBITOR (SNRI) and is used as an ANTIDEPRESSIVE AGENT.	2.08	1	0	hydrochloride
trazodone hydrochloride Triticum: A plant genus of the family POACEAE that is the source of EDIBLE GRAIN. A hybrid with rye (SECALE CEREALE) is called TRITICALE. The seed is ground into FLOUR and used to make BREAD, and is the source of WHEAT GERM AGGLUTININS.. trazodone hydrochloride : A hydrochloride salt prepared from equimolar amounts of trazodone and hydrogen chloride.	4.31	17	0	hydrochloride	adrenergic antagonist; antidepressant; H1-receptor antagonist; sedative; serotonin uptake inhibitor
trovafloxacin trovafloxacin: a trifluoronaphthyridone derivative of 7-(3-azabicyclo(3.1.0)hexyl)naphthyridone; has antineoplastic activity. trovafloxacin : A 1,8-naphthyridine derivative that is 4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid bearing additional 2,4-difluorophenyl, fluoro and 6-amino-3-azabicyclo[3.1.0]hex-3-yl substituents at positions 1, 6 and 7 respectively. A broad-spectrum antibiotic that was withdrawn from the market due to risk of liver failure.	2.1	1	0
4-[1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol [no description available]	3.1	1	0	stilbenoid
glycosine glycosine: structure	2.05	1	0	quinazolines
glucose, (beta-d)-isomer beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.	8.97	182	0	D-glucopyranose	epitope; mouse metabolite
lanthanum chloride lanthanum chloride: RN given refers to parent cpd	2	1	0
dihydrochalcone dihydrochalcone : A member of the class of dihydrochalcones that is acetophenone in which one of the hydrogens of the methyl group is replaced by a benzyl group.	2.07	1	0	dihydrochalcones	plant metabolite
2',7'-dichlorofluorescein 2',7'-dichlorofluorescein: RN given refers to parent cpd	3.1	1	0	2-benzofurans	fluorochrome
ursolic acid [no description available]	8.88	11	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	geroprotector; plant metabolite
meglumine antimoniate Meglumine Antimoniate: ANTIMONY salt of meglumine that is used in the treatment of LEISHMANIASIS.	2.25	1	0
1,5-anhydroglucitol 1,5-anhydroglucitol: structure. 1,5-anhydro-D-glucitol : An anhydro sugar of D-glucitol.	2.52	2	0	anhydro sugar	human metabolite
thiazolyl blue thiazolyl blue: RN & II refers to bromide. 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide : The bromide salt of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium.	3.15	5	0	organic bromide salt	colorimetric reagent; dye
thymidine 5'-triphosphate thymidine 5'-triphosphate: RN given refers to parent cpd. dTTP : A thymidine phosphate having a triphosphate group at the 5'-position.	2.03	1	0	pyrimidine 2'-deoxyribonucleoside 5'-triphosphate; thymidine phosphate	Escherichia coli metabolite; mouse metabolite
betulinic acid [no description available]	5.26	8	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	anti-HIV agent; anti-inflammatory agent; antimalarial; antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; plant metabolite
baicalin [no description available]	2.07	1	0	dihydroxyflavone; glucosiduronic acid; glycosyloxyflavone; monosaccharide derivative	antiatherosclerotic agent; antibacterial agent; anticoronaviral agent; antineoplastic agent; antioxidant; cardioprotective agent; EC 2.7.7.48 (RNA-directed RNA polymerase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; ferroptosis inhibitor; neuroprotective agent; non-steroidal anti-inflammatory drug; plant metabolite; prodrug
diminazene aceturate [no description available]	2.02	1	0
epigallocatechin gallate epigallocatechin gallate: a steroid 5alpha-reductase inhibitor and antimutagen in green tea (Camellia sinensis). (-)-epigallocatechin 3-gallate : A gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (-)-epigallocatechin.	10.45	124	1	flavans; gallate ester; polyphenol	antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite
alpha-terthienyl [no description available]	2.06	1	0	terthiophene
fluorexon fluorexon: structure	2.43	2	0	xanthene dye	fluorochrome
gallocatechol gallocatechol: structure give in first source; RN given for (trans-(+-))-omer; inhibits DNA-dependent DNA & RNA polymerases. (+)-gallocatechin : A gallocatechin that has (2R,3S)-configuration. It is found in green tea and bananas.. gallocatechin : A catechin that is a flavan substituted by hydroxy groups at positions 3, 3', 4', 5, 5' and 7 (the trans isomer). It is isolated from Acacia mearnsii.	6.22	31	1	gallocatechin	antioxidant; metabolite; radical scavenger
10,10'-dimethyl-9,9'-biacridinium 10,10'-dimethyl-9,9'-biacridinium: chemoluminescent probe; RN given refers to dinitrate; Lucigenin refers to dinitrate	1.99	1	0
salvin salvin: a biocyclic diterpenoid; from sage and rosemary (Lamiaceae)	2.66	2	0	abietane diterpenoid; carbotricyclic compound; catechols; monocarboxylic acid	angiogenesis modulating agent; anti-inflammatory agent; antineoplastic agent; antioxidant; apoptosis inducer; food preservative; HIV protease inhibitor; plant metabolite
1,2-dipalmitoylphosphatidylglycerol dipalmitoyl phosphatidylglycerol : A phosphatidylglycerol in which the phosphatidyl acyl groups are both palmitoyl.	1.97	1	0	phosphatidylglycerol
metaperiodate Periodic Acid: A strong oxidizing agent.	2.13	1	0	iodine oxoacid
neocuproine neocuproine: Spectrophotometric determination of copper and ultramicro blood sugar determinations; structure; RN given refers to parent cpd. neocuproine : A member of the class of phenanthrolines that is 1,10-phenanthroline bearing two methyl substituents at positions 2 and 9.	2.44	2	0	phenanthrolines	chelator; copper chelator
1,2,3,4,6-pentakis-O-galloyl-beta-D-glucose pentagalloylglucose: pentahydroxy gallic acid ester of glucose; a phytogenic antineoplastic agent and antibacterial agent. 1,2,3,4,6-pentakis-O-galloyl-beta-D-glucose : A galloyl-beta-D-glucose compound having five galloyl groups in the 1-, 2-, 3-, 4- and 6-positions.	6.1	38	0	gallate ester; galloyl beta-D-glucose	anti-inflammatory agent; antineoplastic agent; geroprotector; hepatoprotective agent; plant metabolite; radiation protective agent; radical scavenger
pyrrolidine dithiocarbamate pyrrolidine dithiocarbamic acid: spelled pyrolidine in J Nutr 1979 reference; RN given refers to parent cpd. pyrrolidine dithiocarbamate : A member of the class of dithiocarbamic acids that is the N-dithiocarboxy derivative of pyrrolidine.	2.69	3	0	dithiocarbamic acids; pyrrolidines	anticonvulsant; antineoplastic agent; geroprotector; neuroprotective agent; NF-kappaB inhibitor; radical scavenger
peroxynitric acid [no description available]	2	1	0	nitrogen oxoacid
glutathione disulfide Glutathione Disulfide: A GLUTATHIONE dimer formed by a disulfide bond between the cysteine sulfhydryl side chains during the course of being oxidized.	2.03	1	0	glutathione derivative; organic disulfide	Escherichia coli metabolite; mouse metabolite
sinefungin [no description available]	1.98	1	0	adenosines; non-proteinogenic alpha-amino acid	antifungal agent; antimicrobial agent
cephalosporin c cephalosporin C: RN given refers to parent cpd; structure in Merck, 9th ed, #1937. cephalosporin C : A cephalosporin antibiotic carrying a 3-acetoxymethyl substituent and a 6-oxo-N(6)-L-lysino group at position 7.	2.57	2	0	cephalosporin	fungal metabolite
16-hydroxytestosterone 16-hydroxytestosterone: RN given refers to (16alpha,17beta)-isomer. 16alpha-hydroxytestosterone : A C19-steroid that is testosterone in which the hydrogen at the 16alpha position has been replaced by a hydroxy group.	3.1	1	0	16alpha-hydroxy steroid; 17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; androstanoid; C19-steroid; diol; secondary alcohol	androgen
rutecarpine rutacarpine: from Evodia rutaecarpa; an ingredient in zhuyu hewei zhitong capsules	1.99	1	0	beta-carbolines
tretoquinol Tretoquinol: An adrenergic beta-agonist used as a bronchodilator agent in asthma therapy.	1.95	1	0	isoquinolines
d 888 devapamil: structure given in first source. devapamil : A nitrile that acts as an L-type calcium channel blocker.	1.97	1	0	aromatic ether; nitrile; tertiary amino compound	anti-arrhythmia drug; calcium channel blocker; vasodilator agent
web 2086 WEB 2086: structure given in first source; PAF antagonist	1.97	1	0	organonitrogen heterocyclic compound; organosulfur heterocyclic compound
methacycline [no description available]	1.96	1	0	1,2-diglyceride
bergenin bergenin: RN refers to (2R-(2alpha,3beta,4alpha,4aalpha,10bbeta))-isomer; structure	4.02	13	0	trihydroxybenzoic acid	metabolite
2-methoxyestradiol 2-methoxy-17beta-estradiol : A 17beta-hydroxy steroid, being 17beta-estradiol methoxylated at C-2.	3.1	1	0	17beta-hydroxy steroid; 3-hydroxy steroid	angiogenesis modulating agent; antimitotic; antineoplastic agent; human metabolite; metabolite; mouse metabolite
hexaconazole 2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol : A member of the class of triazoles that is 1-hexyl-1H-1,2,4-triazole in which the hydrogens at position 2 of the hexyl chain are replaced by hydroxy and 2,4-dichlorophenyl groups.. hexaconazole : A racemate comprising equimolar amounts of (R)- and (S)-hexaconazole. An agricultural fungicide introduced in the 1980s, it is not approved for use within the European Union.	2.08	1	0	dichlorobenzene; tertiary alcohol; triazoles	chelator
2,4,6-trihydroxybenzoic acid [no description available]	3.48	2	0	hydroxybenzoic acid
violuric acid violuric acid: an antihypoxic agent	2.47	2	0
salicylhydroxamic acid [no description available]	2.41	2	0	hydroxamic acid; phenols	antibacterial drug; EC 1.11.2.2 (myeloperoxidase) inhibitor; EC 3.5.1.5 (urease) inhibitor; trypanocidal drug
xanthoxyline xanthoxyline: isolated from Sebastiania schottiana (Euphorbiaceae); structure given in first source; also present in Xanthoxylum, Rutaceae, Artemisia and other plants	2.1	1	0	carboxylic ester
fast blue bb Fast Blue BB: RN given refers to parent cpd	2.06	1	0
thiamorpholine thiamorpholine: RN given refers to parent cpd. thiomorpholine : A saturated organic heteromonocyclic parent that is an analogue of morpholine where the oxygen atom is replaced by sulfur.	2.1	1	0	saturated organic heteromonocyclic parent; thiomorpholines
2-ethoxybenzoic acid [no description available]	1.96	1	0
1,7-phenanthroline [no description available]	2.73	3	0	phenanthroline
triazoles Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.	2.68	3	0	1,2,3-triazole
pinocembrin pinocembrin : A dihydroxyflavanone in which the two hydroxy groups are located at positions 5 and 7. A natural product found in Piper sarmentosum and Cryptocarya chartacea.	2.5	2	0	(2S)-flavan-4-one; dihydroxyflavanone	antineoplastic agent; antioxidant; metabolite; neuroprotective agent; vasodilator agent
2,4,6-trihydroxyacetophenone monoacetylphloroglucinol: structure in first source. 2',4',6'-trihydroxyacetophenone : A benzenetriol that is acetophenone in which the hydrogens at positions 2, 4, and 6 on the phenyl group are replaced by hydroxy groups. It is used as a matrix in matrix-assisted laser desorption/ionization (MALDI) mass spectrometry for the analysis of acidic glycans and glycopeptides.	2.13	1	0	aromatic ketone; benzenetriol; methyl ketone	MALDI matrix material; plant metabolite
2,4,6-trihydroxybenzaldehyde 2,4,6-trihydroxybenzaldehyde: structure in first source	2.78	3	0	carboxylic ester
isocoumarins Isocoumarins: Compounds that differ from COUMARINS in having the positions of the ring and ketone oxygens reversed so the keto oxygen is at the 1-position of the molecule.. isocoumarin : The simplest member of the class of isocoumarins that is 1H-isochromene which is substituted by an oxo group at position 1.	2.01	1	0	isocoumarins
5-hydroxyflavone [no description available]	2.13	1	0	flavones
pyromeconic acid pyromeconic acid: from herb Dengzhanhua; structure	2.17	1	0
coumalic acid coumalic acid: RN given for parent cpd	2.07	1	0	pyranone
phenylacetylglycine phenylacetylglycine : A N-acylglycine that is glycine substituted on nitrogen with a phenylacetyl group.	2.08	1	0	monocarboxylic acid amide; monocarboxylic acid; N-acylglycine	human metabolite; mouse metabolite
2,6-dimethyl-1,4-benzoquinone [no description available]	1.99	1	0
delphinidin Paraffin: A mixture of solid hydrocarbons obtained from petroleum. It has a wide range of uses including as a stiffening agent in ointments, as a lubricant, and as a topical anti-inflammatory. It is also commonly used as an embedding material in histology.. delphinidin chloride : An anthocyanidin chloride that has delphinidin as the cationic counterpart.	2.01	1	0	anthocyanidin chloride
5,6,7,8-tetrahydro-1-naphthol 5,6,7,8-tetrahydro-1-naphthol : 1-naphthol hydrogenated at C-5, -6, -7 and -8.	3.1	1	0	tetralins
sesamol sesamol: constituent of sesame oil; RN given refers to parent cpd; structure in first source	2.94	4	0	benzodioxoles
n-acetyltyrosine N-acetyl-L-tyrosine : An N-acetyltyrosine in which the chiral centre has L configuration.	2.05	1	0	N-acetyltyrosine; N-acyl-L-tyrosine	biomarker; EC 2.1.1.4 (acetylserotonin O-methyltransferase) inhibitor; human urinary metabolite
alfatradiol alfatradiol: used for treating androgenetic alopecia. 17alpha-estradiol : An estradiol that is estra-1,3,5(10)-triene substituted by hydroxy groups at positions 3 and 17 (the 17alpha stereoisomer).	3.1	1	0	17alpha-hydroxy steroid; 3-hydroxy steroid; estradiol	estrogen; geroprotector
pirozadil pirozadil: structure	2.65	3	0	trihydroxybenzoic acid
4-hydroxyquinoline 4-quinolone : A quinolone that is 1,4-dihydroquinoline substituted by an oxo group at position 4.	3.1	1	0	monohydroxyquinoline; quinolone
glycyl-glycyl-glycyl-glycine [no description available]	2.1	1	0
malvidin chloride [no description available]	3.27	1	0
allomaltol allomaltol: structure in first source	2.17	1	0
isoscopoletin isoscopoletin : A hydroxycoumarin that is esculetin in which the hydroxy group at position 7 is replaced by a methoxy group. It is the major primary metabolite of scoparone.	2.05	1	0	aromatic ether; hydroxycoumarin	plant metabolite
methyl syringate methyl syringate : A benzoate ester obtained by the formal condensation of carboxy group of syringic acid with methanol.	5.63	22	0	benzoate ester; dimethoxybenzene; phenols	plant metabolite
2,3,4-trihydroxbenzophenone 2,3,4-trihydroxbenzophenone : A benzenetriol that is benzophenone in which one of the phenyl groups is substituted by hydroxy groups at positions 2, 3, and 4. It is a redox mediator.	2.04	1	0	benzenetriol; hydroxybenzophenone	drug metabolite; EC 1.14.18.1 (tyrosinase) inhibitor; human urinary metabolite; quorum sensing inhibitor; rat metabolite
n-methylscopolamine N-Methylscopolamine: A muscarinic antagonist used to study binding characteristics of muscarinic cholinergic receptors.	2.4	2	0
cromakalim Cromakalim: A potassium-channel opening vasodilator that has been investigated in the management of hypertension. It has also been tried in patients with asthma. (Martindale, The Extra Pharmacopoeia, 30th ed, p352)	1.98	1	0
nebivolol 2,2'-iminobis[1-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)ethanol] : A member of the class of chromanes that is 2,2'-iminodiethanol in which one hydrogen attached to each hydroxy-bearing carbon is replaced by a 6-fluorochroman-2-yl group.	2.1	1	0	chromanes; diol; organofluorine compound; secondary alcohol; secondary amino compound
tyloxapol tyloxapol: non-ionic detergent with surface-active properties; incompatible with metals; surfactant also used in inhalation therapy; N1 is from CA Vol 90 Form Index; N1 in Chemline is same as synonym 8. tyloxapol : A polymeric compound resulting from the reaction of 4-(1,1,3,3-tetramethylbutyl)phenol with formaldehyde to give a chain in which 6-8 molecules are linked together by CH2 groups ortho to the phenolic hydroxy groups, which have then undergone reaction with oxirane to give polyoxyethyleneoxy moieties, Ar(OCH2CH2)xOH, where x = 8-10. A nonionic liquic polymer, it inhibits lipoprotein lipase and hence clearance of triglyceride from the plasma, so is used to induce hyperlipidaemia in test animals. Also used as a surfactant to aid liquefaction and removal of mucus- and pus-containing bronchopulmonary secretions.	2.17	1	0
masoprocol Masoprocol: A potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. The compound also inhibits formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase to a lesser extent. It also serves as an antioxidant in fats and oils.. masoprocol : The meso-form of nordihydroguaiaretic acid. An antioxidant found in the creosote bush, Larrea divaricata, it is a potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. It also inhibits (though to a lesser extent) formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase.	3.37	7	0	nordihydroguaiaretic acid	antineoplastic agent; hypoglycemic agent; lipoxygenase inhibitor; metabolite
tocophersolan tocophersolan: RN given refers to parent cpd	2.63	2	0	tocol
carazolol carazolol: RN given refers to parent cpd without isomeric designation; structure	2.1	1	0	carbazoles
fagomine fagomine: structure in first source	2.04	1	0	piperidines
epicatechin (-)-epicatechin : A catechin with (2R,3R)-configuration.	3.85	11	0	catechin; polyphenol	antioxidant
gallocatechol (-)-epigallocatechin : A flavan-3,3',4',5,5',7-hexol having (2R,3R)-configuration.	4.12	4	0	catechin; flavan-3,3',4',5,5',7-hexol	antioxidant; food component; plant metabolite
hesperetin [no description available]	3.92	3	0	3'-hydroxyflavanones; 4'-methoxyflavanones; monomethoxyflavanone; trihydroxyflavanone	antineoplastic agent; antioxidant; plant metabolite
methotrimeprazine Methotrimeprazine: A phenothiazine with pharmacological activity similar to that of both CHLORPROMAZINE and PROMETHAZINE. It has the histamine-antagonist properties of the antihistamines together with CENTRAL NERVOUS SYSTEM effects resembling those of chlorpromazine. (From Martindale, The Extra Pharmacopoeia, 30th ed, p604). methotrimeprazine : A member of the class of phenothiazines that is 10H-phenothiazine substituted by a (2R)-3-(dimethylamino)-2-methylpropyl group and a methoxy group at positions 10 and 2 respectively.	2.1	1	0	phenothiazines; tertiary amine	anticoronaviral agent; cholinergic antagonist; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; non-narcotic analgesic; phenothiazine antipsychotic drug; serotonergic antagonist
magnolol [no description available]	2.46	2	0	biphenyls
tetrahydropalmatine [no description available]	2.07	1	0	an (S)-7,8,13,14-tetrahydroprotoberberine; berberine alkaloid; organic heterotetracyclic compound	adrenergic agent; dopaminergic antagonist; non-narcotic analgesic
sesamin (+)-sesamin : A lignan that consists of tetrahydro-1H,3H-furo[3,4-c]furan substituted by 1,3-benzodioxole groups at positions 1 and 4 (the 1S,3aR,4S,6aR stereoisomer). Isolated from Cinnamomum camphora, it exhibits cytotoxic activity.	2.91	3	0	benzodioxoles; furofuran; lignan	antineoplastic agent; neuroprotective agent; plant metabolite
betulin betulin: isolated from various white birch bark (BETULA). betulin : A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-hydroxymethyl substituents.	2.01	1	0	diol; pentacyclic triterpenoid	analgesic; anti-inflammatory agent; antineoplastic agent; antiviral agent; metabolite
oleandomycin [no description available]	2.1	1	0	oleandomycins
3-deazaaristeromycin 3-deazaaristeromycin: antagonist of S-adenosylhomocysteinase	1.96	1	0
alantolactone alantolactone: allergenic sesquiterpene lactone; crystalline mixture of alantolactones from group of sesquiterpenes; structure. alantolactone : A sesquiterpene lactone that is 3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2-one bearing two methyl substituents at positions 5 and 8a as well as a methylidene substituent at position 3.	2.07	1	0	naphthofuran; olefinic compound; sesquiterpene lactone	antineoplastic agent; apoptosis inducer; plant metabolite
serpentine (alkaloid) serpentine (alkaloid): do not confuse with mineral serpentine; RN given refers to (19alpha)-isomer; structure	2.15	1	0	carboxylic ester; iminium betaine; indole alkaloid; quinolizines; zwitterion
sennoside A sennoside A : A member of the class of sennosides that is rel-(9R,9'R)-9,9',10,10'-tetrahydro-9,9'-bianthracene-2,2'-dicarboxylic acid which is substituted by hydroxy groups at positions 4 and 4', by beta-D-glucopyranosyloxy groups at positions 5 and 5', and by oxo groups at positions 10 and 10'. The exact stereochemisty at positions 9 and 9' is not known - it may be R,R (as shown) or S,S.	2.05	1	0	oxo dicarboxylic acid; sennosides
beta-amyrin beta-amyrin: alpha-amyrin is also available; a 5 ring triterpene derived from oleanane that differs from alpha-amyrin in having the 29-carbon at the 20 position; RN given refers to (3 beta)-isomer. beta-amyrin : A pentacyclic triterpenoid that is oleanane substituted at the 3beta-position by a hydroxy group and containing a double bond between positions 12 and 13. It is one of the most commonly occurring triterpenoids in higher plants.	3.13	5	0	pentacyclic triterpenoid; secondary alcohol	Aspergillus metabolite; plant metabolite
(-)-catechin (-)-catechin : The (-)-enantiomer of catechin.	2.49	2	0	catechin	metabolite
alpha-amyrin alpha-amyrin: beta-amyrin is also available; a 5 ring triterpene derived from taraxasterol that differs from beta-amyrin in having the 29-carbon at the 19 position. alpha-amyrin : A pentacyclic triterpenoid that is ursane which contains a double bond between positions 12 and 13 and in which the hydrogen at the 3beta position is substituted by a hydroxy group.	2.49	2	0	pentacyclic triterpenoid; secondary alcohol
1,2,3,6-tetragalloylglucose 1,2,3,6-tetragalloylglucose: structure given in first source. 1,2,3,6-tetrakis-O-galloyl-beta-D-glucose : A galloyl-beta-D-glucose compound having four galloyl groups in the 1-, 2-, 3- and 6-positions.	3.09	5	0	gallate ester; galloyl beta-D-glucose
3,5-di-tert-butyl-4-hydroxybenzaldehyde 3,5-di-tert-butyl-4-hydroxybenzaldehyde: structure in first source	2.13	1	0	hydroxybenzaldehyde
isoalantolactone isoalantolactone: RN given refers to (3aR-(3aalpha,4aalpha,8abeta,9aalpha))-isomer; structure. isoalantolactone : A sesquiterpene lactone of the eudesmanolide group. It has been isolated from Inula helenium.	2.07	1	0	eudesmane sesquiterpenoid; sesquiterpene lactone	antifungal agent; apoptosis inducer; plant metabolite
strictinin strictinin: antioxidant from green tea leaves (Camellia sinensis L.); structure in first source	8	4	0
magnoflorine magnoflorine: opium alkaloid having the aporphine configuration; RN given refers to parent cpd(S)-isomer; structure. (S)-magnoflorine : An aporphine alkaloid that is (S)-corytuberine in which the nitrogen has been quaternised by an additional methyl group.	2.06	1	0	aporphine alkaloid; quaternary ammonium ion	plant metabolite
calpeptin [no description available]	2.1	1	0	amino acid amide
madecassic acid [no description available]	2.1	1	0	monocarboxylic acid; pentacyclic triterpenoid; tetrol	antioxidant; plant metabolite
corilagin corilagin: isolated from Geranii herba. corilagin : An ellagitannin with a hexahydroxydiphenoyl group bridging over the 3-O and 6-O of the glucose core.	5.77	26	0	ellagitannin; gallate ester	antihypertensive agent; antioxidant; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; non-steroidal anti-inflammatory drug
arjunolic acid arjunolic acid: oleanane type; isol from Cochlospermum tinctorium (Bixaceae); structure given in first source; RN given refers to (2alpha,3beta,4alpha)-isomer; RN for cpd without isomeric designation not avail 12/89. arjunolic acid : A pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by hydroxy groups at positions 2, 3 and 23 (the 2alpha,3beta stereoisomer). Isolated from Symplocos lancifolia and Juglans sinensis, it exhibits antioxidant and antimicrobial activities.	3.35	1	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	antibacterial agent; antifungal agent; antioxidant; metabolite
casuarictin sanguiin H 11: regulates chemotaxis of neutrophil; from plant, Sanguisorba officinalis; structure in first source	2.41	2	0	tannin
maslinic acid (2Alpha,3beta)-2,3-dihydroxyolean-12-en-28-oic acid: from Luehea divaricata and Agrimonia eupatoria	2.17	1	0	dihydroxy monocarboxylic acid; pentacyclic triterpenoid	anti-inflammatory agent; antineoplastic agent; antioxidant; plant metabolite
carbohydrazide carbohydrazide: structure. carbohydrazide : A hydrazide consisting of hydrazine carrying one or more carboacyl groups.. carbonyl dihydrazine : A carbohydrazide obtained by formal condensation between hydrazinecarboxylic acid and hydrazine.	2.11	1	0	carbohydrazide; one-carbon compound
ceric oxide ceric oxide: RN given refers to cpd with MF CeO2. ceric oxide : A metal oxide with formula CeO2. It is used for polishing glass, in coatings for infra-red filters to prevent reflection, and as an oxidant and catalyst in organic synthesis.	2.63	2	0	cerium molecular entity; metal oxide
triphenylmethylphosphonium triphenylmethylphosphonium: RN given refers to parent cpd	1.96	1	0
3,4-dimethoxy-5-hydroxybenzoic acid 3,4-dimethoxy-5-hydroxybenzoic acid: thiopurine methyltransferase inhibitor	2.9	4	0	trihydroxybenzoic acid
1,3,7,9-tetramethyluric acid 1,3,7,9-tetramethyluric acid: RN from CHEMID. 1,3,7,9-tetramethyluric acid : An oxopurine that is uric acid in which the hydrogens at positions 1,3,7 and 9 are replaced by methyl groups. It is a purine alkaloid that is found in Chinese tea known as kucha (Camellia assamica var. kucha) and exhibits anti-inflammatory and analgesic properties.	2.25	1	0	oxopurine; purine alkaloid	analgesic; anti-inflammatory agent; human xenobiotic metabolite; plant metabolite
citronellal, (r)-isomer (R)-(+)-citronellal : The (3R)-stereoisomer of 3,7-dimethyloct-6-enal (citronellal).	2.01	1	0	citronellal
n-(hydroxymethyl)carbazole N-(hydroxymethyl)carbazole: structure given in first source	2.1	1	0
phenylalanyl-phenylalanyl-phenylalanine phenylalanyl-phenylalanyl-phenylalanine: RN given refers to all (L)-isomer	2.1	1	0	oligopeptide
1-hydroxybenzotriazole 1-hydroxybenzotriazole: RN given refers to parent cpd	2.05	1	0	benzotriazoles
3-(4-methoxybenzoyl)propionic acid 3-(4-methoxybenzoyl)propionic acid: a selectin inhibitor	2.1	1	0
dimethylaminopropanol dimethylaminopropanol: dimethylamine precursor	2.1	1	0
ethyl protocatechuate ethyl protocatechuate: structure. ethyl 3,4-dihydroxybenzoate : An ethyl ester resulting from the formal condensation of the carboxy group of 3,4-dihydroxybenzoic acid with ethanol. It is the anti-oxidative component of peanut seed testa.	2.17	1	0	catechols; ethyl ester	antibacterial agent; antioxidant; apoptosis inducer; EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor; plant metabolite
2',7'-dichlorodihydrofluorescein diacetate [no description available]	2.1	1	0
4'-methoxyflavone 4'-methoxyflavone: from seeds of Psoralea corylifolia (Fabaceae); structure in first source	2.1	1	0	ether; flavonoids
rivastigmine [no description available]	2.49	2	0	carbamate ester; tertiary amino compound	cholinergic drug; EC 3.1.1.8 (cholinesterase) inhibitor; neuroprotective agent
tamiflu [no description available]	2.1	1	0	phosphate salt
3,5-dihydroxy-4-methoxybenzoic acid 3,5-dihydroxy-4-methoxybenzoic acid: catechol methyltransferase inhibitor; N1 same as NM	7.82	29	7	trihydroxybenzoic acid
dodecyltetraethylene glycol monoether [no description available]	2.05	1	0	poly(ethylene glycol)
glucose alpha-D-glucose : D-Glucopyranose having alpha-configuration at the anomeric centre.. (1->6)-alpha-D-glucan : An alpha-D-glucan in which the glucose units are connected by (1->6) linkages.. (1->3)-alpha-D-glucan : An alpha-D-glucan in which the glucose units are connected by (1->3) linkages.	2.03	1	0	D-glucopyranose	mouse metabolite
n-hydroxysuccinimide N-hydroxysuccinimide: structure	2.13	1	0
gallanilide [no description available]	3.06	5	0
3,7-dimethyl-7-octen-1-ol Geranium: A plant genus of the family GERANIACEAE. Geranium is also used as a common name for PELARGONIUM.	2.47	2	0
s20098 [no description available]	2.15	1	0	acetamides
nonyl gallate [no description available]	2.95	4	0
3,4-dihydroxyphenylethanol 3,4-dihydroxyphenylethanol: serotonin metabolite; structure	4.29	5	0	catechols; primary alcohol	antineoplastic agent; antioxidant; metabolite
4-phenylbutylamine 4-phenylbutylamine: used as a drug partition into lipid bilayers in a cubic liquid-crystalline phase. 4-phenylbutylamine : A phenylalkylamine that is benzene in which one of the hydrogens is substituted by a 4-aminobutyl group.	2.1	1	0	benzenes; phenylalkylamine; primary amino compound
eriocitrin eriocitrin: structure in first source. eriocitrin : A disaccharide derivative that consists of eriodictyol substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	3.27	1	0	3'-hydroxyflavanones; 4'-hydroxyflavanones; disaccharide derivative; flavanone glycoside; rutinoside; trihydroxyflavanone	antioxidant
3,4,5-trihydroxybenzaldehyde 3,4,5-trihydroxybenzaldehyde: isolated from Geum japonicum; structure in first source	2.5	2	0
3-(trimethoxysilyl)propylamine 3-(trimethoxysilyl)propylamine: reagent for making polymers; structure in first source	2.15	1	0
clarithromycin Clarithromycin: A semisynthetic macrolide antibiotic derived from ERYTHROMYCIN that is active against a variety of microorganisms. It can inhibit PROTEIN SYNTHESIS in BACTERIA by reversibly binding to the 50S ribosomal subunits. This inhibits the translocation of aminoacyl transfer-RNA and prevents peptide chain elongation.. clarithromycin : The 6-O-methyl ether of erythromycin A, clarithromycin is a macrolide antibiotic used in the treatment of respiratory-tract, skin and soft-tissue infections. It is also used to eradicate Helicobacter pylori in the treatment of peptic ulcer disease. It prevents bacteria from growing by interfering with their protein synthesis.	2.1	1	0	macrolide antibiotic	antibacterial drug; environmental contaminant; protein synthesis inhibitor; xenobiotic
asperuloside asperuloside : A iridoid monoterpenoid glycoside isolated from Galium verum.	2.02	1	0	acetate ester; beta-D-glucoside; gamma-lactone; iridoid monoterpenoid; monosaccharide derivative	metabolite
bromates Bromates: Negative ions or salts derived from bromic acid, HBrO3.	2.05	1	0	bromine oxoanion; monovalent inorganic anion
3,4-dihydroxymandelic acid 3,4-dihydroxymandelic acid: metabolite of L-dopa; RN given refers to parent cpd without isomeric designation. 3,4-dihydroxymandelic acid : A catechol that is the 3,4-dihydroxy derivative of mandelic acid; a metabolite of L-dopa.	1.96	1	0	2-hydroxy monocarboxylic acid; catechols	antioxidant; drug metabolite; human metabolite; mouse metabolite
loganin [no description available]	2.43	2	0	beta-D-glucoside; cyclopentapyran; enoate ester; iridoid monoterpenoid; methyl ester; monosaccharide derivative; secondary alcohol	anti-inflammatory agent; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; EC 3.4.23.46 (memapsin 2) inhibitor; neuroprotective agent; plant metabolite
glycinexylidide glycinexylidide: dealkylated metabolite of lidocaine; structure; RN given refers to parent cpd with dimethylphenyl moiety in positions 2,6. glycinexylidide : A amino acid amide with 2,6-dimethylaniline and glycine components; an active metabolite of lidocaine, formed by oxidative deethylation. Used as an indicator of hepatic function.	2.1	1	0	amino acid amide	drug metabolite
Trp-Trp tryptophyltryptophan: an antigelation agent. Trp-Trp : A dipeptide formed from two L-tryptophan residues.	2.1	1	0	dipeptide	Mycoplasma genitalium metabolite
gentiopicroside gentiopicroside: a secoiridoid in Gentiana with rearrangement to two pyran rings	2.41	1	0	glycoside
kampirone 1-(2-pyrimidinyl)piperazine: metabolite of buspirone; structure given in first source	2.1	1	0	N-arylpiperazine
5,7-dimethoxyflavone chrysin 5,7-dimethyl ether : A dimethoxyflavone that is the 5,7-dimethyl ether derivative of chrysin.	2.13	1	0	dimethoxyflavone	plant metabolite
mebeverine gamma-oryzanol: present in rice bran is associated with various physiological functions; RN given refers to gamma-oryzanol	2.15	1	0
nicotine (S)-nicotine : A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has S-configuration. The naturally occurring and most active enantiomer of nicotine, isolated from Nicotiana tabacum.	3.07	5	0	3-(1-methylpyrrolidin-2-yl)pyridine	anxiolytic drug; biomarker; immunomodulator; mitogen; neurotoxin; nicotinic acetylcholine receptor agonist; peripheral nervous system drug; phytogenic insecticide; plant metabolite; psychotropic drug; teratogenic agent; xenobiotic
sennoside B sennoside B : A member of the class of sennosides that is (9R,9'S)-9,9',10,10'-tetrahydro-9,9'-bianthracene-2,2'-dicarboxylic acid which is substituted by hydroxy groups at positions 4 and 4', by beta-D-glucopyranosyloxy groups at positions 5 and 5', and by oxo groups at positions 10 and 10'.	2.01	1	0	oxo dicarboxylic acid; sennosides
17-alpha-hydroxypregnenolone 17-alpha-Hydroxypregnenolone: A 21-carbon steroid that is converted from PREGNENOLONE by STEROID 17-ALPHA-HYDROXYLASE. It is an intermediate in the delta-5 pathway of biosynthesis of GONADAL STEROID HORMONES and the adrenal CORTICOSTEROIDS.. 17alpha-hydroxypregnenolone : A hydroxypregnenolone carrying an alpha-hydroxy group at position 17.	3.1	1	0	17alpha-hydroxy-C21-steroid; 17alpha-hydroxy steroid; 3beta-hydroxy-Delta(5)-steroid; hydroxypregnenolone; tertiary alpha-hydroxy ketone	human metabolite; mouse metabolite
aucubin [no description available]	2.07	1	0	organic molecular entity	metabolite
friedelin 3-friedelanone: from the stem bark of Irvingia gabonensis; structure in first source. friedelin : A pentacyclic triterpenoid that is perhydropicene which is substituted by an oxo group at position 3 and by methyl groups at the 4, 4a, 6b, 8a, 11, 11, 12b, and 14a-positions (the 4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS-enantiomer). It is the major triterpenoid constituent of cork.	3.15	5	0	cyclic terpene ketone; pentacyclic triterpenoid	anti-inflammatory drug; antipyretic; non-narcotic analgesic; plant metabolite
cadmium telluride cadmium telluride: used in radiation monitoring device	2.25	1	0
goethite [no description available]	2.25	1	0
catalpol [no description available]	2.07	1	0	organic molecular entity	metabolite
homocysteine Homocysteine: A thiol-containing amino acid formed by a demethylation of METHIONINE.. homocysteine : A sulfur-containing amino acid consisting of a glycine core with a 2-mercaptoethyl side-chain.. L-homocysteine : A homocysteine that has L configuration.	5.22	6	2	amino acid zwitterion; homocysteine; serine family amino acid	fundamental metabolite; mouse metabolite
5-(3-hydroxyphenyl)-5-phenylhydantoin 5-(3-hydroxyphenyl)-5-phenylhydantoin: metabolite of phenytoin; RN given refers to cpd without isomeric designation	3.1	1	0
8-((4-chlorophenyl)thio)cyclic-3',5'-amp 8-((4-chlorophenyl)thio)cyclic-3',5'-AMP: lowers cAMP in heart & fat cells; cAMP-dependent kinase inhibitor. 8-(4-chlorophenylthio)-cAMP : A 3',5'-cyclic purine nucleotide that is 3',5'-cyclic AMP in which the hydrogen at position 2 on the purine fragment is replaced by a 4-chlorophenylthio group.	1.97	1	0	3',5'-cyclic purine nucleotide; adenyl ribonucleotide; aryl sulfide; organochlorine compound	protein kinase agonist
fosthiazate fosthiazate: structure in first source	2.07	1	0	organic phosphonate; organothiophosphate insecticide; phosphonic ester	agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor; nematicide
taraxerol taraxerol: structure. taraxerol : A pentacyclic triterpenoid that is oleanan-3-ol lacking the methyl group at position 14, with an alpha-methyl substituent at position 13 and a double bond between positions 14 and 15.	3.18	5	0	pentacyclic triterpenoid; secondary alcohol	metabolite
beta-amyrin acetate [no description available]	2.04	1	0	triterpenoid
spathulenol [no description available]	2.49	2	0	carbotricyclic compound; olefinic compound; sesquiterpenoid; tertiary alcohol	anaesthetic; plant metabolite; vasodilator agent; volatile oil component
7-amino-4-methylcoumarin 7-amino-4-methylcoumarin: RN given refers to parent cpd	3.1	1	0	7-aminocoumarins	fluorochrome
11-hydroxyprogesterone, (11alpha)-isomer 11alpha-hydroxyprogesterone : A 11alpha-hydroxy steroid that is pregn-4-ene-3,20-dione substituted by a hydroxy group at position 11.	3.1	1	0	11alpha-hydroxy steroid; 20-oxo steroid; 3-oxo-Delta(4) steroid
taraxerone taraxerone: structure	2.04	1	0	scalarane sesterterpenoid	metabolite
brexanolone brexanolone: a mixture of allopregnanolone and sulfobutylether‐beta‐cyclodextrin for treatment of postpartum depression. brexanolone : A 3-hydroxy-5alpha-pregnan-20-one in which the hydroxy group at position 3 has alpha-configuration. It is a metabolite of the sex hormone progesterone and used for the treatment of postpartum depression in women.	3.1	1	0	3-hydroxy-5alpha-pregnan-20-one	antidepressant; GABA modulator; human metabolite; intravenous anaesthetic; sedative
uvaol uvaol: from Vauquelinia corymbosa (Rosaceae)	2.08	1	0	triterpenoid	metabolite
3,5-diiodothyronine, (l)-isomer [no description available]	3.1	1	0	phenylalanine derivative
isopelletierine isopelletierine: RN given refers to cpd without isomeric designation; synonym pelletierine refers to (-)-isomer	2.1	1	0	citraconoyl group
glycidyl nitrate glycidyl nitrate: a nitric oxide donor; structure in first source. peptidoglycan : A peptidoglycosaminoglycan formed by alternating residues of beta-(1->4)-linked N-acetylglucosamine and N-acetylmuramic acid {2-amino-3-O-[(S)-1-carboxyethyl]-2-deoxy-D-glucose} residues. Attached to the carboxy group of the muramic acid is a peptide chain of three to five amino acids.	2.13	1	0
6-methoxy-8-hydroxy-3-methyl-3,4-dihydroisocoumarin 6-methoxy-8-hydroxy-3-methyl-3,4-dihydroisocoumarin: structure given in first source; a phytoalexin isolated from Daucus carota	2.01	1	0	isochromanes
titanium nitride (tin) titanium nitride: RN given refers to unspecified MF	2.15	1	0
n-dodecanoylglutamic acid N-dodecanoylglutamic acid: RN refers to (DL)-isomer; structure given in first source	2.07	1	0
xanthorrhizol xanthorrhizol: structure in first source	2.11	1	0	sesquiterpenoid
fenpropimorph [no description available]	2.1	1	0	alkylbenzene
6-deoxyglucose 6-deoxyglucose: RN given refers to (D)-isomer; Main Heading DEOXYGLUCOSE refers to 2-deoxyglucose	1.96	1	0	quinovose
1,2-hexanediol [no description available]	2.11	1	0
pyrogallol sulfonphthalein [no description available]	2.08	1	0
1-(2-pyridinyl)piperazine 1-(2-pyridinyl)piperazine: metabolite of buspirone & gepirone	2.1	1	0
harmol hydrochloride [no description available]	3.1	1	0
diprotin a [no description available]	3.27	1	0	peptide
glucuronic acid Glucuronic Acid: A sugar acid formed by the oxidation of the C-6 carbon of GLUCOSE. In addition to being a key intermediate metabolite of the uronic acid pathway, glucuronic acid also plays a role in the detoxification of certain drugs and toxins by conjugating with them to form GLUCURONIDES.. D-glucuronic acid : The D-enantiomer of glucuronic acid.. D-glucopyranuronic acid : A D-glucuronic acid in cyclic pyranose form.	2.78	3	0	D-glucuronic acid	algal metabolite
2-hydroxy-5-methoxybenzaldehyde 2-hydroxy-5-methoxybenzaldehyde: structure in first source. 5-methoxysalicylaldehyde : A member of the class of benzaldehydes carrying hydroxy and methoxy substituents at positions 2 and 5 respectively.	2.25	1	0	benzaldehydes; monomethoxybenzene; phenols
10-hydroxycamptothecin [no description available]	2.04	1	0	pyranoindolizinoquinoline
quindoline quindoline: a fused indole-quinoline alkaloid from CRYPTOLEPIS sanguinolenta; structure	2.17	1	0
diosgenin [no description available]	3.1	1	0	3beta-sterol; hexacyclic triterpenoid; sapogenin; spiroketal	antineoplastic agent; antiviral agent; apoptosis inducer; metabolite
sarsasapogenin, (3beta,5alpha,25r)-isomer tigogenin : A widely used steroidal sapogenin isolated from several plant species and used for synthesizing steroid drugs.	3.1	1	0	sapogenin	gout suppressant; plant metabolite
m3omg M3OMG: has antidepressant activity	3.29	6	0
syringaresinol [no description available]	2.47	2	0	aromatic ether; furofuran; lignan; polyether; polyphenol	plant metabolite
carbobenzoxyphenylalanylmethionine [no description available]	1.96	1	0
loliolide loliolide: RN given refers to (6S-cis)-isomer	1.96	1	0	benzofurans	metabolite
coumarin 6 coumarin 6: structure in first source	2.25	1	0	7-aminocoumarins	fluorochrome
karanjin karanjin: structure given in first source	2.1	1	0	extended flavonoid
chimaphilin chimaphilin: isolated from Chimaphila umbellata; structure given in first source	2.52	2	0	1,4-naphthoquinones
friedelinol friedelinol: isolated from seeds of Aster auriculatus Franch; structure given in first source; RN given refers to friedelanol (friedelinol), the (3alpha)-isomer	2.03	1	0
sesamolin sesamolin: constituent of sesame oil; RN given refers to the (1S-(1alpha,3aalpha,4alpha,6aalpha)-isomer); inhibits proliferation of human lymphocytic leukemia cells in culture	2.25	1	0	benzodioxoles
3 alpha,17 alpha-dihydroxy-5 beta-pregnan-20-one 3alpha,17alpha-dihydroxy-5beta-pregnan-20-one : A 17alpha-hydroxy steroid that is 3alpha-hydroxy-5beta-pregnan-20-one carrying an additional hydroxy group at position 17alpha.	3.1	1	0	17alpha-hydroxy steroid; 20-oxo steroid; 3alpha-hydroxy steroid; C21-steroid; corticosteroid hormone	human urinary metabolite
2-methoxyestriol [no description available]	3.1	1	0
cobalt Cobalt: A trace element that is a component of vitamin B12. It has the atomic symbol Co, atomic number 27, and atomic weight 58.93. It is used in nuclear weapons, alloys, and pigments. Deficiency in animals leads to anemia; its excess in humans can lead to erythrocytosis.. cobalt(1+) : A monovalent inorganic cation obtained from cobalt.. cobalt atom : A cobalt group element atom that has atomic number 27.	4.03	14	0	cobalt group element atom; metal allergen	micronutrient
p-methoxy-n-methylphenethylamine p-Methoxy-N-methylphenethylamine: A potent mast cell degranulator. It is involved in histamine release.. N,O-dimethyltyramine : A secondary amino compound that is tyramine in which the hydrogen of the phenolic hydroxy group has been replaced by a methyl group.	3.68	10	0	aromatic ether; secondary amino compound	metabolite
1,2-bis(2-aminophenoxy)ethane-n,n,n',n'-tetraacetic acid 1,2-bis(2-aminophenoxy)ethane-N,N,N',N'-tetraacetic acid: structure in first source	4.06	15	0	polyamino carboxylic acid; tetracarboxylic acid	chelator
1-amino-1,3-dicarboxycyclopentane 1-amino-1,3-dicarboxycyclopentane: RN given refers to (cis)-isomer	2	1	0
u 73122 1-(6-((3-methoxyestra-1,3,5(10)-trien-17-yl)amino)hexyl)-1H-pyrrole-2,5-dione: structure given in first source. U-73122 : An aza-steroid that is 3-O-methyl-17beta-estradiol in which the 17beta-hydroxy group is replaced by a 6-(maleimid-1-yl)hexylamino group. An inibitor of phospholipase C.	4.15	16	0	aromatic ether; aza-steroid; maleimides	EC 3.1.4.11 (phosphoinositide phospholipase C) inhibitor
arginyl-glycyl-aspartic acid arginyl-glycyl-aspartic acid: amino acid sequence of basic unit of widespread cellular recognition system	2.81	3	0	oligopeptide
vitamin b 6 Vitamin B 6: VITAMIN B 6 refers to several PICOLINES (especially PYRIDOXINE; PYRIDOXAL; & PYRIDOXAMINE) that are efficiently converted by the body to PYRIDOXAL PHOSPHATE which is a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, and aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into PYRIDOXAMINE phosphate. Although pyridoxine and Vitamin B 6 are still frequently used as synonyms, especially by medical researchers, this practice is erroneous and sometimes misleading (EE Snell; Ann NY Acad Sci, vol 585 pg 1, 1990). Most of vitamin B6 is eventually degraded to PYRIDOXIC ACID and excreted in the urine.	3.4	1	1
1,4-dihydropyridine [no description available]	1.97	1	0
quin2 Quin2: fluorescent highly selective Ca indicator, binding Ca 1:1; structure given in first source	3.84	12	0
diacetyldichlorofluorescein diacetyldichlorofluorescein: stable storage form of dichlorofluorescein	3.82	2	1
eudragit rs Eudragit RS: copolymer of acrylic & methacrylic acid esters & quaternary ammonium groups; used for microcapsules	2.25	1	0
2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine: directly acting genotoxic metabolite of 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine. N-hydroxy-PhIP : An imidazopyridine that is 1H--imidazo[4,5-b]pyridine which is substituted at positions 1, 2, and 6 by methyl, hydoxyamino, and phenyl groups, respectively. The active metabolite of the dietary carcinogen PhIP.	3.1	1	0	hydroxylamine; imidazopyridine	carcinogenic agent; genotoxin; human xenobiotic metabolite; mouse metabolite; mutagen; neurotoxin; rat metabolite
1-(2-(3-(4-methoxyphenyl)propoxy)-4-methoxyphenylethyl)-1h-imidazole 1-(2-(3-(4-methoxyphenyl)propoxy)-4-methoxyphenylethyl)-1H-imidazole: inhibits platelet aggregation & Ca2+ entry into platelets. SKF-96365 free base : An ether that is 2-(1H-imidazol-1-yl)-1-(4-methoxyphenyl)ethanol in which the hydrogen of the hydroxy group has been substituted by a 3-(4-methoxyphenyl)propyl group.	1.99	1	0	ether; imidazoles; monomethoxybenzene	TRP channel blocker
fluo-3 Fluo-3: fluorescent Ca(2+) indicator; permits continuous monitoring of Ca without interference with use of UV-sensitive caged compounds	2.43	2	0	xanthene dye	fluorochrome
fpl 55712 FPL 55712: inhibitor of SRS-A and LTC4 and LTD4 receptors	1.96	1	0	aromatic ketone
prolinedithiocarbamate prolinedithiocarbamate: do not confuse with pyrrolidine dithiocarbamate which is also abbreviated PDTC	2.13	1	0
indo-1 indo-1: structure given in first source	2.38	2	0	indoles	fluorochrome
fura-2-am fura-2-am: pentaester precursor of fura-2	2.41	2	0
quin2-acetoxymethyl ester Quin2-acetoxymethyl ester: structure given in first source	3.07	5	0
thiamethoxam Thiamethoxam: A nitro-oxazine and thiazole derivative that is used as a broad spectrum neonicotinoid insecticide.. thiamethoxam : An oxadiazane that is tetrahydro-N-nitro-4H-1,3,5-oxadiazin-4-imine bearing (2-chloro-1,3-thiazol-5-yl)methyl and methyl substituents at positions 3 and 5 respectively.	2.31	1	0	1,3-thiazoles; 2-nitroguanidine derivative; organochlorine compound; oxadiazane	antifeedant; carcinogenic agent; environmental contaminant; neonicotinoid insectide; xenobiotic
s-ethyl glutathione [no description available]	2.01	1	0	oligopeptide
l-lactic acid (S)-lactic acid : An optically active form of lactic acid having (S)-configuration.	2.1	1	0	(2S)-2-hydroxy monocarboxylic acid; 2-hydroxypropanoic acid	Escherichia coli metabolite; human metabolite
bismuth nitrate [no description available]	1.98	1	0
22-hydroxycholesterol [no description available]	2	1	0	cholanoid
inositol-1,3,4,5-tetrakisphosphate inositol-1,3,4,5-tetrakisphosphate: for cpd without numerical locants of phosphate groups, index INOSITOL PHOSPHATES. 1D-myo-inositol 1,3,4,5-tetrakisphosphate : A myo-inositol tetrakisphosphate having the four phosphates placed in the 1-, 3-, 4- and 5-positions.	1.98	1	0	inositol phosphate
methoctramine methoctramine: structure given in first source. methoctramine : A tetramine that is N,N'-bis(6-aminohexyl)octane-1,8-diamine where the primary amino groups both carry 2-methoxybenzyl substituents.. methoctramine tetrahydrochloride : A hydrochloride obtained by combining methoctramine with four molar equivalents of hydrochloric acid.	1.99	1	0	hydrochloride	muscarinic antagonist
tryptoline tryptoline: neurotoxic factor that may be involved in development of Parkinson's disease; enzymatic prep from human brain converts tryptamine to tryptoline; RN given refers to parent cpd; structure	2.17	1	0	beta-carbolines
geniposide [no description available]	2.13	1	0	terpene glycoside
procyanidin Proanthocyanidins: Dimers and oligomers of flavan-3-ol units (CATECHIN analogs) linked mainly through C4 to C8 bonds to leucoanthocyanidins. They are structurally similar to ANTHOCYANINS but are the result of a different fork in biosynthetic pathways.	5.27	48	0	proanthocyanidin
dityrosine dityrosine: o,o'-biphenol analog of tyrosine; isolated from insoluble protein of human cataractous lenses; structure. dityrosine : A biphenyl compound comprising two tyrosine residues linked at carbon-3 of their benzene rings.	2.01	1	0	biphenyls; non-proteinogenic alpha-amino acid; tyrosine derivative	biomarker
epicatechin gallate epicatechin gallate: a steroid 5alpha-reductase inhibitor; RN given refers to the (cis)-isomer; structure given in first source; isolated from green tea. (-)-epicatechin-3-O-gallate : A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of epicatechin. A natural product found in Parapiptadenia rigida.	6.1	36	0	catechin; gallate ester; polyphenol	EC 3.2.1.1 (alpha-amylase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; metabolite
ecopipam ecopipam: structure given in first source	3.1	1	0	benzazepine
daidzin daidzin: a potent, selective, and reversible inhibitor of human mitochondrial aldehyde dehydrogenase. daidzein 7-O-beta-D-glucoside : A glycosyloxyisoflavone that is daidzein attached to a beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage. It is used in the treatment of alcohol dependency (antidipsotropic).	2.46	2	0	7-hydroxyisoflavones 7-O-beta-D-glucoside; hydroxyisoflavone; monosaccharide derivative	plant metabolite
sri 63-441 SRI 63-441: structure given in first source; PAF antagonist	1.97	1	0
ml 9 [no description available]	2.4	2	0
proanthocyanidin proanthocyanidin: RN given refers to proanthocyanidin A; Cannabinoid Receptor CB1 antagonist. proanthocyanidin : A flavonoid oligomer obtained by the the condensation of two or more units of hydroxyflavans.	3.55	8	0
kt 5823 KT 5823: indolocarbazole; activates human neutrophils & fails to inhibit cGMP-dependent protein kinase phosphorylation of vimentin. KT 5823 : An organic heterooctacyclic compound that is 1H,1'H-2,2'-biindole in which the nitrogens have undergone formal oxidative coupling to positions 2 and 5 of methyl (3R)-3-methoxy-2-methyltetrahydrofuran-3-carboxylate (the 2S,3R,5R product), and in which the 3 and 3' positions of the biindole moiety have also undergone formal oxidative coupling to positions 3 and 4 of 1-methyl-1,5-dihydro-2H-pyrrol-2-one.	2.41	2	0	gamma-lactam; hemiaminal; indolocarbazole; methyl ester; organic heterooctacyclic compound	EC 2.7.11.12 (cGMP-dependent protein kinase) inhibitor
1-hexadecyl-2-acetyl-glycero-3-phosphocholine Platelet Activating Factor: A phospholipid derivative formed by PLATELETS; BASOPHILS; NEUTROPHILS; MONOCYTES; and MACROPHAGES. It is a potent platelet aggregating agent and inducer of systemic anaphylactic symptoms, including HYPOTENSION; THROMBOCYTOPENIA; NEUTROPENIA; and BRONCHOCONSTRICTION.. 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine : A 2-acetyl-1-alkyl-sn-glycero-3-phosphocholine betaine which has hexadecyl as the alkyl group. PAF is a potent phospholipid activator and mediator of many leukocyte functions, including platelet aggregation, inflammation, and anaphylaxis.	3.99	14	0	2-acetyl-1-alkyl-sn-glycero-3-phosphocholine	antihypertensive agent; beta-adrenergic antagonist; bronchoconstrictor agent; hematologic agent; vasodilator agent
testosterone 17-glucosiduronate testosterone glucuronate: natural conjugate isolated from human plasma; RN given refers to (beta)-isomer. testosterone 17-glucosiduronic acid : A steroid glucosiduronic that is testosterone carrying a glucosiduronic acid residue at position 17.	2.07	1	0	3-oxo steroid; beta-D-glucosiduronic acid; enone; steroid glucosiduronic acid	human metabolite
deoxyglucose Deoxyglucose: 2-Deoxy-D-arabino-hexose. An antimetabolite of glucose with antiviral activity.. deoxyglucose : A deoxyhexose comprising glucose having at least one hydroxy group replaced by hydrogen.	4.34	19	0
5,6-dihydroxyindole [no description available]	2.1	1	0	dihydroxyindole	mouse metabolite
st 587 St 587: clonidine derivative which is selective alpha(1)-adrenoceptor stimulator with lipophilic properties; structure in first source	1.97	1	0
2,3-bis(3'-hydroxybenzyl)butyrolactone 2,3-bis(3'-hydroxybenzyl)butyrolactone: lignan isolated from urine of humans & other mammals; RN given refers to cpd without isomeric designation; structure given in second source	2.03	1	0	lignan
3',4'-dichlorobenzamil 3',4'-dichlorobenzamil: inhibits Na-Ca exchange in membrane vesicle & papillary muscle preparations from guinea pig heart	1.98	1	0	guanidines; pyrazines
homoorientin homoorientin: isolated from Swertia japonica; structure given in first source	2.42	2	0	flavone C-glycoside; tetrahydroxyflavone	antineoplastic agent; radical scavenger
u 73343 U 73343: an inactive analog of U 73122	2.02	1	0
liquiritigenin liquiritigenin: structure given in first source; isolated from Pterocarpus marsupium. 4',7-dihydroxyflavanone : A dihydroxyflavanone in which the two hydroxy substituents are located at positions 4' and 7.. liquiritigenin : A dihydroxyflavanone compound having the two hydroxy substituents at the 4'- and 7-positions. Isolated from the root of Glycyrrhizae uralensis, it is a selective agonist for oestrogen receptor beta.	3.31	1	0	4',7-dihydroxyflavanone	hormone agonist; plant metabolite
3-deoxyglucosone 3-deoxyglucosone: RN given refers to (D)-isomer. 3-deoxyglucosone : A deoxyketohexose comprising the open-chain form of D-glucose lacking the -OH group at the 3-position and having the keto group at the 2-position.	2.15	1	0	deoxyglucose; deoxyketohexose
ibuprofen, (r)-isomer [no description available]	3.54	2	0	ibuprofen
thromboxanes thromboxane : A class of oxygenated oxane derivatives, originally derived from prostaglandin precursors in platelets, that stimulate aggregation of platelets and constriction of blood vessels.	3.22	6	0
11-hydroxytestosterone 11-hydroxytestosterone: RN given refers to (11 beta,17 beta)-isomer. 11beta-hydroxytestosterone : An androstanoid that is testosterone carrying an additional hydroxy substituent at the 11beta-position.	3.1	1	0	11beta-hydroxy steroid; 17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; androstanoid; C19-steroid	bacterial xenobiotic metabolite; human xenobiotic metabolite; marine metabolite
pumiliotoxin c pumiliotoxin C: isolated from skin of Dendrobates pumilio (frog); see also records for pumiliotoxin A, pumiliotoxin B & pumiliotoxins	2.17	1	0
norbuprenorphine norbuprenorphine: metabolite of buprenorphine found in urine & feces; RN given refers to (5alpha,7alpha)-isomer; structure given in first source	3.1	1	0	phenanthrenes
bn 50739 BN 50739: platelet activating factor antagonist; structure given in first source	2.38	2	0
geraniin Geraniin: in various plants; structure in first source	2.97	4	0
2,5-bis(3,4,5-trimethoxyphenyl)tetrahydrofuran 2,5-bis(3,4,5-trimethoxyphenyl)tetrahydrofuran: orally active & competitive receptor antagonist of platelet activating factor; structure given in first source	1.98	1	0
stachydrine stachydrine: RN given refers to hydroxide inner salt (S)-isomer; structure. L-proline betaine : An amino acid betaine that is L-proline zwitterion in which both of the hydrogens attached to the nitrogen are replaced by methyl groups.	3.3	6	0	alkaloid; amino-acid betaine; N-methyl-L-alpha-amino acid	food component; human blood serum metabolite; plant metabolite
echinuline echinuline: tri-isoprenylated cyclic dipeptide from Aspergillus amstelodami; structure; Rn given refers to (3S-cis)-isomer. echinulin : An indole alkaloid with formula C29H39N3O2. It is a fungal metabolite found in several Aspergillus species.	2.04	1	0	2,5-diketopiperazines; indole alkaloid; indoles; olefinic compound	Aspergillus metabolite; marine metabolite; plant metabolite
asiatic acid [no description available]	2.49	2	0	monocarboxylic acid; pentacyclic triterpenoid; triol	angiogenesis modulating agent; metabolite
astilbin astilbin: dihydroflavonol from Kohki tea processed from Engelhardtia chrysolepis (huang-qui); astilbin is the (2R-trans)-isomer; neoisoastilbin is the (2S-cis)-isomer and is Sweetening Agents; isoastilbin is the (2R-cis)-isomer; structure in first source;. astilbin : A flavanone glycoside that is (+)-taxifolin substituted by a alpha-L-rhamnosyl moiety at position 3 via a glycosidic linkage.	2.6	1	0	3'-hydroxyflavanones; 4'-hydroxyflavanones; alpha-L-rhamnoside; flavanone glycoside; monosaccharide derivative; tetrahydroxyflavanone	anti-inflammatory agent; plant metabolite; radical scavenger
benzo(a)pyrene-3,6-quinol [no description available]	3.1	1	0
cd 349 CD 349: structure given in first source	2.38	2	0
caprylates Caprylates: Derivatives of caprylic acid. Included under this heading are a broad variety of acid forms, salts, esters, and amides that contain a carboxy terminated eight carbon aliphatic structure.. octanoate : A straight-chain saturated fatty acid anion that is the conjugate base of octanoic acid (caprylic acid); believed to block adipogenesis.	2.55	2	0	fatty acid anion 8:0; straight-chain saturated fatty acid anion	human metabolite; Saccharomyces cerevisiae metabolite
1,3,4-thiadiazole 1,3,4-thiadiazole: structure given in first source	7.6	1	0	thiadiazole
1-hydroxyethyl radical ethoxide : An organic anion that is the conjugate base of ethanol.	2.08	1	0	organic anion	human metabolite; Saccharomyces cerevisiae metabolite
deramciclane deramciclane: structure in first source; RN refers to (exo-EGYT 3886)-isomer	2.1	1	0
pentosidine pentosidine: structure given in first source. pentosidine : An imidazopyridine having norleucine and ornithine residues attached via their side-chains at the 4- and 2-positions respectively.	2.15	1	0	imidazopyridine; non-proteinogenic L-alpha-amino acid	biomarker; cross-linking reagent
2,3-dihydro-3,5-dihydroxy-6-methyl-4h-pyran-4-one 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one: a Maillard reaction product of glucose and glycine; structure in first source	2.06	1	0
allitol allitol: structure in first source	2.04	1	0	hexitol
nepitrin [no description available]	2	1	0	flavonoids; glycoside
2-o-methylpyrogallol 2-O-methylpyrogallol: metabolite of gallic acid; structure in first source	2.4	2	0	methoxybenzenes; phenols
egta acetoxymethyl ester EGTA acetoxymethyl ester: membrane-permeable form of EGTA	2.41	2	0
diazaquinomycin a diazaquinomycin A: structure given in first source	2.17	1	0	quinolone
l 659989 L 659989: structure given in first source; platelet activating factor receptor antagonist; RN given refers to cpd without isomeric designation	1.97	1	0
1-ethyl-3-(3-dimethylaminoethyl)carbodiimide 1-ethyl-3-(3-dimethylaminoethyl)carbodiimide: carboxyl modifying agent	2.13	1	0
erythrose 4-phosphate erythrose 4-phosphate: RN given refers to (R-(R,R))-isomer. D-erythrose 4-phosphate : An erythrose phosphate that is D-erythrose carrying a phosphate group at position 4. It is an intermediate in the pentose phosphate pathway and Calvin cycle.	2	1	0	erythrose phosphate	Escherichia coli metabolite; human metabolite; mouse metabolite
procyanidin b2 procyanidin B2 : A proanthocyanidin consisting of two molecules of (-)-epicatechin joined by a bond between positions 4 and 8' in a beta-configuration. Procyanidin B2 can be found in Cinchona pubescens (Chinchona, in the rind, bark and cortex), in Cinnamomum verum (Ceylon cinnamon, in the rind, bark and cortex), in Crataegus monogyna (Common hawthorn, in the flower and blossom), in Uncaria guianensis (Cat's claw, in the root), in Vitis vinifera (Common grape vine, in the leaf), in Litchi chinensis (litchi, in the pericarp), in the apple, in Ecdysanthera utilis and in red wine.	4.67	8	0	biflavonoid; hydroxyflavan; polyphenol; proanthocyanidin	antioxidant; metabolite
4'-demethylepipodophyllotoxin 4'-demethylepipodophyllotoxin: structure in first source. 4'-demethylepipodophyllotoxin : An organic heterotetracyclic compound that is the 9- epimer of 4'-demethylpodophyllotoxin.	1.97	1	0	furonaphthodioxole; organic heterotetracyclic compound; phenols	antineoplastic agent
betulonic acid betulonic acid: isolated from Rush javanica; strucure in first source	2.11	1	0	triterpenoid	anticoronaviral agent
aromadedrin aromadedrin: inhibits protein kinase C; the dihydro makes it a flavone rather than a flavonol. (+)-dihydrokaempferol : A tetrahydroxyflavanone having hydroxy groupa at the 3-, 4'-, 5- and 7-positions.	2.98	4	0	4'-hydroxyflavanones; dihydroflavonols; secondary alpha-hydroxy ketone; tetrahydroxyflavanone	metabolite
phenoxy radical phenoxy radical : An organic radical generated from phenol.	1.97	1	0	organic radical
peroxynitrous acid Peroxynitrous Acid: A potent oxidant synthesized by the cell during its normal metabolism. Peroxynitrite is formed from the reaction of two free radicals, NITRIC OXIDE and the superoxide anion (SUPEROXIDES).	4.07	4	0	nitrogen oxoacid
fullerene c60 Fullerenes: A polyhedral CARBON structure composed of around 60-80 carbon atoms in pentagon and hexagon configuration. They are named after Buckminster Fuller because of structural resemblance to geodesic domes. Fullerenes can be made in high temperature such as arc discharge in an inert atmosphere.. fullerene : A compound composed solely of an even number of carbon atoms, which form a cage-like fused-ring polycyclic system with twelve five-membered rings and the rest six-membered rings. The term has been broadened to include any closed cage structure consisting entirely of three-coordinate carbon atoms.	3.33	6	0	fullerene	geroprotector
imatinib mesylate imatinib methanesulfonate : A methanesulfonate (mesylate) salt that is the monomesylate salt of imatinib. Used for treatment of chronic myelogenous leukemia and gastrointestinal stromal tumours.	2.52	2	0	methanesulfonate salt	anticoronaviral agent; antineoplastic agent; apoptosis inducer; tyrosine kinase inhibitor
gefitinib [no description available]	2.13	1	0	aromatic ether; monochlorobenzenes; monofluorobenzenes; morpholines; quinazolines; secondary amino compound; tertiary amino compound	antineoplastic agent; epidermal growth factor receptor antagonist
prolyl-phenylalanyl-arginine-4-nitroanilide prolyl-phenylalanyl-arginine-4-nitroanilide: chromogenic cpd	2.88	1	0
(3,4-dihydroxyphenylamino)-2-imidazoline (3,4-dihydroxyphenylamino)-2-imidazoline: potent agonist at dopamine receptors mediating neuronal inhibition; RN given refers to parent cpd; structure in UD indicates phenyl-imino group	2.02	1	0
cgp 42112a CGP 42112A: a hexapeptide analog of angiotensin II; activation of Receptor, Angiotensin, Type 2 results in vasodilation. CGP-42112A : A hexapeptide consisting of L-tyrosine, L-lysine, L-histidine, L-proline and L-isoleucine amino acid residues coupled in sequence and in which the amino group of the L-tyrosyl residue is substituted by a (pyridin-3-ylcarbonyl)nitrilo group and in which the L-lysyl side chain amino group is substituted by a {N(2)-[(benzyloxy)carbonyl]-L-arginyl}nitrilo group. It is a potent angiotensin II receptor type 2 (AT2 receptor) agonist.	1.98	1	0	benzyl ester; oligopeptide; pyridinecarboxamide	angiotensin receptor agonist; anti-inflammatory agent; antineoplastic agent; neuroprotective agent; vasodilator agent
n(6)-carboxymethyllysine N(6)-carboxymethyllysine: RN given refers to (L)-isomer; structure given in first source. N(6)-carboxymethyl-L-lysine : An L-lysine derivative with a carboxymethyl substituent at the N(6)-position.	2.53	2	0	L-lysine derivative; non-proteinogenic L-alpha-amino acid	antigen
cyclic adp-ribose Cyclic ADP-Ribose: A pyridine nucleotide that mobilizes CALCIUM. It is synthesized from nicotinamide adenine dinucleotide (NAD) by ADP RIBOSE CYCLASE.	2.41	2	0	cyclic purine nucleotide; nucleotide-sugar	metabolite; ryanodine receptor agonist
cgp 28392 CGP 28392: partial calcium channel agonist; structure given in first source	1.97	1	0	aromatic ether
benzoylarginine ethyl ester benzoylarginine ethyl ester: used as substrate for trypsin; RN given refers to parent cpd	2.74	3	0
1-((3,5-dichloro)-2,6-dihydroxy-4-methoxyphenyl)-1-hexanone 1-((3,5-dichloro)-2,6-dihydroxy-4-methoxyphenyl)-1-hexanone: structure given in first source. 1-(3,5-dichloro-2,6-dihydroxy-4-methoxyphenyl)hexan-1-one : A differentiation-inducing factor that is hexaphenone bearing two chloro substituents at positions 3 and 5, two hydroxy substituents at positions 2 and 6 as well as a single methoxy substituent at position 4. A secreted, chlorinated molecule that controls cell fate during development of Dictyostelium cells.	3.37	7	0	dichlorobenzene; differentiation-inducing factor; monomethoxybenzene; resorcinols	eukaryotic metabolite; signalling molecule
indo-1 pentaacetoxymethyl ester Indo-1 pentaacetoxymethyl ester: calcium-specific chelating agent; calcium ion fluorescent probe	1.97	1	0
naadp nicotinic acid-adenine dinucleotide phosphate : A nicotinic acid dinucleotide that is NADP(+) in which the carboxamide group on the pyridine ring is replaced by a carboxy group.	1.99	1	0	nicotinic acid dinucleotide	calcium channel agonist; metabolite; signalling molecule
procyanidin b2-3,3'-di-o-gallate procyanidin B2-3,3'-di-O-gallate: structure in first source	2	1	0	flavonoid oligomer
proanthocyanidin a2 procyanidin A2: structure in first source. proanthocyanidin A2 : A proanthocyanidin obtained by the condensation of (-)-epicatechin units.	2.85	3	0	hydroxyflavan; proanthocyanidin	angiogenesis modulating agent; anti-HIV agent; antioxidant; metabolite
fraxinellone fraxinellone: structure given in first source; RN given for (3R-cis)-isomer	2.17	1	0	2-benzofurans
glabridin [no description available]	2.17	1	0	hydroxyisoflavans	antiplasmodial drug
glucogallin glucogallin: RN given refers to (D-glucose)-isomer	10.34	17	0
4,5-diaminopentanoic acid 4,5-diaminopentanoic acid: structure given in first source; RN given is for parent cpd without isomeric designation	1.98	1	0
methotrexate [no description available]	2.84	3	0	dicarboxylic acid; monocarboxylic acid amide; pteridines	abortifacient; antimetabolite; antineoplastic agent; antirheumatic drug; dermatologic drug; DNA synthesis inhibitor; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; immunosuppressive agent
u 66985 U 66985: structure given in first source	1.97	1	0
3,4,5-tri-o-galloylquinic acid 3,4,5-tri-O-galloylquinic acid: DNA polymerase inhibitor; structure given in first source	3.29	6	0
2-n-propyl-3-dimethylamino-5,6-methylenedioxyindene 2-n-propyl-3-dimethylamino-5,6-methylenedioxyindene: affects calcium-induced arrhythmias; RN given refers to parent cpd	1.96	1	0
2-n-butyl-3-(dimethylamino)-5,6-methylenedioxyindene 2-n-butyl-3-(dimethylamino)-5,6-methylenedioxyindene: affects calcium-induced arrhythmias; RN given refers to parent cpd	1.97	1	0
delphinidin delphinidin: RN given refers to parent cpd;. delphinidin : An anthocyanidin cation consisting of benzopyrylium with hydroxy substituents at the 3-, 5- and 7-positions and a 3,4,5-trihydroxyphenyl group at the 2-position. It is a plant pigment responsible for the colours of the plants of the genera Viola and Delphinium.	3.51	7	0	5-hydroxyanthocyanidin	antineoplastic agent; biological pigment; plant metabolite
cyanidin cyanidin: RN given refers to parent cpd; structure. cyanidin cation : An anthocyanidin cation that is flavylium substituted at positions 3, 3', 4', 5 and 7 by hydroxy groups.	3.04	4	0	5-hydroxyanthocyanidin	antioxidant; metabolite; neuroprotective agent
methyl-beta-d-fructoside methylfructoside: RN given refers to (beta-D)-isomer	2.02	1	0
wl 19 WL 19: structure given in first source; angiotensin II type 2 receptor antagoinst	1.98	1	0
cornuside cornuside: a bisiridoid glucoside from Cornus officinalis Sieb et Zucc; structure given in first source	2.04	1	0
6-bromo-3-(bromomethyl)-7-methyl-2,3,7-trichloro-1-octene 6-bromo-3-(bromomethyl)-7-methyl-2,3,7-trichloro-1-octene: structure given in first source	2.17	1	0	monoterpenoid; organobromine compound; organochlorine compound	algal metabolite; antineoplastic agent; marine metabolite
4-(3,4,4-trimethyl-5-oxo-2-thioxo-1-imidazolidinyl)-2-(trifluoromethyl)benzonitrile 4-(3,4,4-trimethyl-5-oxo-2-thioxo-1-imidazolidinyl)-2-(trifluoromethyl)benzonitrile: a non-steroidal antiandrogen; structure given in first source	1.99	1	0
omega-n-methylarginine omega-N-Methylarginine: A competitive inhibitor of nitric oxide synthetase.. N(omega)-methyl-L-arginine : A L-arginine derivative with a N(omega)-methyl substituent.	2.4	2	0	amino acid zwitterion; arginine derivative; guanidines; L-arginine derivative; non-proteinogenic L-alpha-amino acid
calcium specific chelator calcium specific chelator: structure in first source; do not confuse with MAPTAM	1.99	1	0
triiodothyronine L-homocysteine thiolactone : A thiolactone arising from formal condensation of the mercapto (sulfanyl) and carboxylic acid groups of L-homocysteine.	1.96	1	0	tetrahydrothiophenes; thiolactone	human metabolite
aspartame [no description available]	2.1	1	0	carboxylic acid; dipeptide zwitterion; dipeptide; methyl ester	apoptosis inhibitor; EC 3.1.3.1 (alkaline phosphatase) inhibitor; environmental contaminant; micronutrient; nutraceutical; sweetening agent; xenobiotic
xylose xylopyranose: structure in first source	2.69	2	0	D-xylose
valerylsalicylate valerylsalicylic acid: significantly inhibited [3H]thymidine; inhibitor of normal epithelial cell proliferation and growth of malignant cells. valerylsalicylic acid : A valerate ester that is salicylic acid in which the phenolic hydrogen is replaced by a valeryl (pentanoyl) group.	2.01	1	0	benzoic acids; salicylates; valerate ester	cyclooxygenase 1 inhibitor
salicylideneaniline salicylideneaniline: structure in first source	7.07	1	0
beta-lactams 2-azetidinone: structure in first source. azetidin-2-one : An unsubstituted beta-lactam compound.. beta-lactam : A lactam in which the amide bond is contained within a four-membered ring, which includes the amide nitrogen and the carbonyl carbon.	3.28	6	0	beta-lactam antibiotic allergen; beta-lactam
phytol [no description available]	4.06	3	0
proline Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.	3.83	11	0	amino acid zwitterion; glutamine family amino acid; L-alpha-amino acid; proline; proteinogenic amino acid	algal metabolite; compatible osmolytes; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
cucurbitaceae Cucurbitaceae: The gourd plant family of the order Violales, subclass Dilleniidae, class Magnoliopsida. It is sometimes placed in its own order, Cucurbitales. 'Melon' generally refers to CUCUMIS; CITRULLUS; or MOMORDICA.	3	4	0
procyanidin b3 procyanidin B3 : A proanthocyanidin consisting of two molecules of (+)-catechin joined by a bond between positions 4 and 8' in alpha-configuration. It can be found in red wine, in barley, in beer, in peach or in Jatropha macrantha, the Huanarpo Macho.	2.8	3	0	biflavonoid; hydroxyflavan; polyphenol; proanthocyanidin	anti-inflammatory agent; antioxidant; EC 2.3.1.48 (histone acetyltransferase) inhibitor; metabolite
6-methoxyflavone 6-methoxyflavone: suppresses NFAT-mediated T cell activation; structure in first source	7.41	1	0	ether; flavonoids
levofloxacin Levofloxacin: The L-isomer of Ofloxacin.. levofloxacin : An optically active form of ofloxacin having (S)-configuration; an inhibitor of bacterial topoisomerase IV and DNA gyrase.	7.83	3	0	9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid; fluoroquinolone antibiotic; quinolone antibiotic	antibacterial drug; DNA synthesis inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; topoisomerase IV inhibitor
4'-chloroflavone 4'-chloroflavone: structure given in first source	2.1	1	0
tellimagrandin ii tellimagrandin II: isolated from Filipendula palmata; structure in first source	3.76	10	0
2,4,6-tribromo-3-hydroxybenzoic acid 2,4,6-tribromo-3-hydroxybenzoic acid: structure given in first source	2.31	1	0
3,3',4,5'-tetrahydroxybibenzyl 3,3',4,5'-tetrahydroxybibenzyl: from Cassia garrettiana; structure given in first source	2	1	0
moxifloxacin Moxifloxacin: A fluoroquinolone that acts as an inhibitor of DNA TOPOISOMERASE II and is used as a broad-spectrum antibacterial agent.. moxifloxacin : A quinolone that consists of 4-oxo-1,4-dihydroquinoline-3-carboxylic acid bearing a cyclopropyl substituent at position 1, a fluoro substitiuent at position 6, a (4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl group at position 7 and a methoxy substituent at position 8. A member of the fluoroquinolone class of antibacterial agents.	2.1	1	0	aromatic ether; cyclopropanes; fluoroquinolone antibiotic; pyrrolidinopiperidine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone	antibacterial drug
phorbols Phorbols: The parent alcohol of the tumor promoting compounds from CROTON OIL (Croton tiglium).	3.75	11	0	diterpene; terpenoid fundamental parent
kolaviron kolaviron: antihepatotoxic fraction of biflavonones from Garcinia kola seeds; phalloidine antagonist. kolaflavanone : A biflavonoid isolated from the seeds of Garcinia kola that has been shown to exhibit hepatoprotective activity.	7.13	1	0	4'-methoxyflavanones; biflavonoid; dihydroflavonols; ring assembly; secondary alpha-hydroxy ketone	hepatoprotective agent; plant metabolite
spinosin spinosin: isolated from seeds of Ziziph spinosa; structure given in first source. spinosin : A flavone C-glycoside that is flavone substituted by hydroxy groups at positions 5 and 4', a methoxy group at position 7 and a 2-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl residue at position 6 via a C-glycosidic linkage.	2.31	1	0	dihydroxyflavone; flavone C-glycoside; monomethoxyflavone	anxiolytic drug; plant metabolite
naproxen Naproxen: An anti-inflammatory agent with analgesic and antipyretic properties. Both the acid and its sodium salt are used in the treatment of rheumatoid arthritis and other rheumatic or musculoskeletal disorders, dysmenorrhea, and acute gout.. naproxen : A methoxynaphthalene that is 2-methoxynaphthalene substituted by a carboxy ethyl group at position 6. Naproxen is a non-steroidal anti-inflammatory drug commonly used for the reduction of pain, fever, inflammation and stiffness caused by conditions such as osteoarthritis, kidney stones, rheumatoid arthritis, psoriatic arthritis, gout, ankylosing spondylitis, menstrual cramps, tendinitis, bursitis, and for the treatment of primary dysmenorrhea. It works by inhibiting both the COX-1 and COX-2 enzymes.	3.54	2	0	methoxynaphthalene; monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; gout suppressant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
birb 796 [no description available]	2.11	1	0	aromatic ether; morpholines; naphthalenes; pyrazoles; ureas	EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; immunomodulator
hydroxyl radical Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.	5.93	30	0	oxygen hydride; oxygen radical; reactive oxygen species
pseudonicotine pseudonicotine: structure. (R)-nicotine : A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has R-configuration.	2.17	1	0	3-(1-methylpyrrolidin-2-yl)pyridine
camphora camphora: a component of Guanxingao, a kind of traditional Chinese rubber electuary medicine which is able to either cure or guard against coronary heart disease and angina pectoris. (R)-camphor : The (R)- enantiomer of camphor.	2.01	1	0	camphor
rhodioloside [no description available]	2.59	2	0	glycoside
malvidin malvidin: RN given refers to parent cpd; coloring agent from flowers of Malvaviscus conzatti. malvidin : An anthocyanidin cation that is delphinidin carrying methyl substituents at positions 3' and 5'.	3.2	5	0	5-hydroxyanthocyanidin	biological pigment; metabolite
yttria yttria: molecular formula Y2-O3	2.13	1	0
singlet oxygen Singlet Oxygen: An excited state of molecular oxygen generated photochemically or chemically. Singlet oxygen reacts with a variety of biological molecules such as NUCLEIC ACIDS; PROTEINS; and LIPIDS; causing oxidative damages.	3.08	4	0	chalcogen; monoatomic oxygen; nonmetal atom	macronutrient
peroxymonosulfate peroxymonosulfate: oxidizing agent in prevention of tooth discoloration; RN given refers to ion(2-)	7.07	1	0	sulfur oxide; sulfur oxoanion
fenton's reagent Fenton's reagent: used for oxidizing sugars & alcohols	7.95	4	0
cyc 202 seliciclib : 2,6-Diaminopurine carrying benzylamino, (2R)-1-hydroxybutan-2-yl and isopropyl substituents at C-6, C-2-N and N-9 respectively. It is an experimental drug candidate in the family of pharmacological cyclin-dependent kinase (CDK) inhibitors.	2.13	1	0	2,6-diaminopurines	antiviral drug; EC 2.7.11.22 (cyclin-dependent kinase) inhibitor
carbodiimides Carbodiimides: Compounds with the general formula RN=C=NR, where R is a hydrocarbyl group.. methanediimine : A carbodiimide in which both nitrogens are unsubstituted.	2.8	3	0	carbodiimide
cortolone [no description available]	3.1	1	0	21-hydroxy steroid
isolariciresinol isolariciresinol: RN given refers to ((1-S-(1alpha,2beta,3alpha))-isomer); structure given in first source. (+)-isolariciresinol : A lignan that is 5,6,7,8-tetrahydronaphthalen-2-ol substituted by hydroxymethyl groups at positions 6 and 7, a methoxy group at position 3 and a 4-hydroxy-3-methoxyphenyl group at position 8. It has been isolated from the roots of Rubia yunnanensis.	2.03	1	0	guaiacols; lignan; polyphenol; primary alcohol	plant metabolite
isoflavanone isoflavanone: structure given in first source; RN from CA Index Guide. isoflavanone : Isoflavone in which the double bond between positions 2 and 3 has been reduced to a single bond.	2	1	0	isoflavanones
rosenthal's inhibitor Rosenthal's inhibitor: RN given refers to acetate salt; inhibits phopholipases A1 and A2	1.96	1	0
sweroside [no description available]	2.49	2	0	glycoside
leonurine leonurine: has neuroprotective activity; isolated from leaves of Leonurus artemisia; has uterotonic effect; structure	9.95	115	1	trihydroxybenzoic acid
gentisuric acid gentisuric acid: structure	2.07	1	0	N-acylglycine
maprounic acid maprounic acid: from Maprounea africana; structure given in first source. maprounic acid : A pentacyclic triterpenoid isolated from Maprounea africana and has been shown to exhibit inhibitory activity against HIV-1 reverse transcriptase.	2.49	2	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	HIV-1 reverse transcriptase inhibitor; plant metabolite
deferrioxamine e deferrioxamine E: may act as siderophore in Streptomyces. desferrioxamine E : A cyclic hydroxamic acid siderophore that is produced by several bacterial species and exhibits antitumour activity.	2.17	1	0	cyclic desferrioxamine; cyclic hydroxamic acid; macrocycle	antineoplastic agent; bacterial metabolite; marine metabolite; siderophore
ampelopsin ampelopsin: hepatoprotective agent; isolated from Hovenia dulcis; RN given for (2R-trans)-isomer; structure in first source. (+)-dihydromyricetin : An optically active form of dihydromyricetin having (2R,3R)-configuration.	2.08	1	0	dihydromyricetin; secondary alpha-hydroxy ketone	antineoplastic agent; antioxidant; metabolite
myricanone myricanone: from stem bark of Myrica rubra; structure given in first source. Myricanone : A cyclic ketone isolated from the bark of Morella species and has been shown to exhibit cytotoxic activity against cancer cells.	2.07	1	0	aromatic ether; cyclic ketone; diarylheptanoid; methoxybenzenes; phenols	antineoplastic agent; plant metabolite
myricanol myricanol: from stem bark of Myrica rubra; RN given for (R)-isomer; structure given in first source	2.07	1	0
isovitexin [no description available]	2.07	1	0	C-glycosyl compound; trihydroxyflavone	EC 3.2.1.20 (alpha-glucosidase) inhibitor; metabolite
8-o-acetyl shanzhiside methyl ester 8-O-acetyl shanzhiside methyl ester: an iridoid glucoside; from Phlomis mongolica Turcz; RN given refers to (1S-(1alpha,4aalpha,5alpha,7alpha,7aalpha))-isomer; structure given in first source	2.11	1	0
methylinositol methylinositol: from Ebenus haussknechtii; structure in first source. pinitol : A cyclitol ether formed by etherification of the 3-hydroxy group of chiro-inositol. It is plant metabolite isolated from the leaves of Sutherlandia frutescens.. 1D-4-O-methyl-myo-inositol : A member of the class of methyl myo-inositols that is cyclohexane-1,2,3,4,5-pentol substituted by a methoxy group at position 6 (the 1R,2S,3S,4S,5S,6S-isomer).. D-pinitol : The D-enantiomer of pinitol.	2.04	1	0
hamaudol hamaudol: intermediate in the synthesis of furanochromones	2.49	2	0	chromenes
ferric thiocyanate [no description available]	2.08	1	0
4'-hydroxyflavanone 4'-hydroxyflavanone: structure in first source. 4'-hydroxyflavanones : Any hydroxyflavanone having a hydroxy substituent located at position 4'.	2.17	1	0	4'-hydroxyflavanones; monohydroxyflavanone
metaperiodate metaperiodate: RN given refers to periodic acid, Na salt; structure. periodate : A monovalent inorganic anion obtained by deprotonation of periodic acid.	2.13	1	0	iodine oxoanion; monovalent inorganic anion
protoporphyrin ix monomethyl ester protoporphyrin IX monomethyl ester: RN given refers to protoporphyrin IX 18-monomethyl ester. protoporphyrin monomethyl ester : A dicarboxylic acid monoester that is the monomethyl ester of protoporphyrin.	2.11	1	0
n-valyltryptophan N-valyltryptophan: RN given refers to (L)-isomer	3.27	1	0	peptide
3-(2-carboxyindol-3-yl)propionic acid 3-(2-carboxyindol-3-yl)propionic acid: structure given in first source; NMDA antagonist	2.17	1	0
procyanidin C1 procyanidin trimer C1: a flavonoid found in multiple plant sources including grape, apple, and cacao, which has antioxidant and anti-inflammatory properties. procyanidin C1 : A proanthocyanidin consisting of three (-)-epicatechin units joined by two successive (4beta->8)-linkages.	2.15	1	0	hydroxyflavan; polyphenol; proanthocyanidin	anti-inflammatory agent; antioxidant; EC 1.17.3.2 (xanthine oxidase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; lipoxygenase inhibitor; metabolite
biotin vitamin B7 : Any member of a group of vitamers that belong to the chemical structural class called biotins that exhibit biological activity against vitamin B7 deficiency. Vitamin B7 deficiency is very rare in individuals who take a normal balanced diet. Foods rich in biotin are egg yolk, liver, cereals, vegetables (spinach, mushrooms) and rice. Symptoms associated with vitamin B7 deficiency include thinning hair, scaly skin rashes around eyes, nose and mouth, and brittle nails. The vitamers include biotin and its ionized and salt forms.	2.48	2	0	biotins; vitamin B7	coenzyme; cofactor; Escherichia coli metabolite; fundamental metabolite; human metabolite; mouse metabolite; nutraceutical; prosthetic group; Saccharomyces cerevisiae metabolite
angiotensin ii Giapreza: injectable form of angiotensin II used to increase blood pressure in adult patients with septic or other distributive shock. Ile(5)-angiotensin II : An angiotensin II that acts on the central nervous system (PDB entry: 1N9V).	9.83	33	0	amino acid zwitterion; angiotensin II	human metabolite
n-formylmethionyl-methionyl-phenylalanine [no description available]	1.96	1	0
3-n-butyl-4,5-dihydrophthalide 3-N-butyl-4,5-dihydrophthalide: from seeds of Apium graveolens Linn.; RN given refers to (-)-isomer; structure given in first source	2.07	1	0
pinoresinol diglucoside pinoresinol diglucoside: major antihypertensive principle of Tu-Chung (Eucummia ulmoides, Oliver); structure	2.25	1	0
atropine tropan-3alpha-yl 3-hydroxy-2-phenylpropanoate : A tropane alkaloid that is (1R,5)-8-methyl-8-azabicyclo[3.2.1]octane substituted by a (3-hydroxy-2-phenylpropanoyl)oxy group at position 3.	4.07	15	0
lignin Lignin: The most abundant natural aromatic organic polymer found in all vascular plants. Lignin together with cellulose and hemicellulose are the major cell wall components of the fibers of all wood and grass species. Lignin is composed of coniferyl, p-coumaryl, and sinapyl alcohols in varying ratios in different plant species. (From Merck Index, 11th ed). lignin : A polyphenylpropanoid derived from three monolignol monomers: trans-p-coumaryl alcohol, coniferol and trans-sinapyl alcohol. There is extensive cross-linking and no defined primary structure.	6.67	28	0
sb 203580 [no description available]	2.97	4	0	imidazoles; monofluorobenzenes; pyridines; sulfoxide	EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector; Hsp90 inhibitor; neuroprotective agent
erlotinib hydrochloride [no description available]	2.13	1	0	hydrochloride; terminal acetylenic compound	antineoplastic agent; protein kinase inhibitor
agn 2979 AGN 2979: RN given refers to parent cpd; structure given in first source	1.96	1	0
(+)-epicatechin (+)-epicatechin : A catechin that is flavan carrying five hydroxy substituents at positions 3, 3', 4', 5 and 7 (the 2S,3S-stereoisomer).	2.07	1	0	catechin; polyphenol	cyclooxygenase 1 inhibitor; plant metabolite
scutellarin scutellarin: see scutellarein for aglycone. scutellarin : The glycosyloxyflavone which is the 7-O-glucuronide of scutellarein.	2.78	3	0	glucosiduronic acid; glycosyloxyflavone; monosaccharide derivative; trihydroxyflavone	antineoplastic agent; proteasome inhibitor
6-o-veratroyl catalpol [no description available]	2.49	2	0
dihydroresveratrol dihydroresveratrol: structure in first source. dihydroresveratrol : A stilbenol that is 1,1'-ethane-1,2-diyldibenzene with hydroxy groups at positions 1, 3 and 4'.	2	1	0	stilbenol	plant metabolite; xenobiotic metabolite
aflatoxin b1 Aflatoxin B1: A potent hepatotoxic and hepatocarcinogenic mycotoxin produced by the Aspergillus flavus group of fungi. It is also mutagenic, teratogenic, and causes immunosuppression in animals. It is found as a contaminant in peanuts, cottonseed meal, corn, and other grains. The mycotoxin requires epoxidation to aflatoxin B1 2,3-oxide for activation. Microsomal monooxygenases biotransform the toxin to the less toxic metabolites aflatoxin M1 and Q1.. aflatoxin B1 : An aflatoxin having a tetrahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h]chromene skeleton with oxygen functionality at positions 1, 4 and 11.	2.73	3	0	aflatoxin; aromatic ether; aromatic ketone	carcinogenic agent; human metabolite
glycitin glycitin: structure in first source. glycitin : A glycosyloxyisoflavone that is isoflavone substituted by a methoxy group at position 6, a hydroxy group at position 4' and a beta-D-glucopyranosyloxy group at position 7.	2.04	1	0	7-hydroxyisoflavones 7-O-beta-D-glucoside; hydroxyisoflavone; methoxyisoflavone; monosaccharide derivative	plant metabolite
cirsimaritin cirsimaritin: has antagonist or partial agonist activity on benzodiazepine receptors. cirsimaritin : A dimethoxyflavone that is flavone substituted by methoxy groups at positions 6 and 7 and hydroxy groups at positions 5 and 4' respectively.	3.27	1	0	dihydroxyflavone; dimethoxyflavone
cgp 42700 CGP 42700: staurosporine derivative	1.99	1	0
hamamelose hamamelose: common sugar of green land plants	2.6	1	0	aldopentose
s-benzylcysteine [no description available]	2.21	1	0	S-aryl-L-cysteine zwitterion
carbocysteine Carbocysteine: A compound formed when iodoacetic acid reacts with sulfhydryl groups in proteins. It has been used as an anti-infective nasal spray with mucolytic and expectorant action.. S-carboxymethyl-L-cysteine : An L-cysteine thioether that is L-cysteine in which the hydrogen of the thiol group has been replaced by a carboxymethyl group.	3.1	1	0	L-cysteine thioether; non-proteinogenic L-alpha-amino acid	mucolytic
(-)-gallocatechin gallate (-)-gallocatechin gallate : A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of (-)-gallocatechin. A natural product found in found in green tea.	3.6	2	0	catechin; gallate ester; polyphenol	antineoplastic agent; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; human xenobiotic metabolite; plant metabolite
anabasine Anabasine: A piperidine botanical insecticide.. (S)-anabasine : The (S)-enantiomer of anabasine.. anabasine : A pyridine alkaloid that is pyridine substituted by a piperidin-2-yl group at position 3.	2.03	1	0	anabasine
tv3326 [no description available]	2.07	1	0	indanes
lapatinib [no description available]	2.11	1	0	furans; organochlorine compound; organofluorine compound; quinazolines	antineoplastic agent; tyrosine kinase inhibitor
cholic acid Cholic Acid: A major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion.. cholic acid : A bile acid that is 5beta-cholan-24-oic acid bearing three alpha-hydroxy substituents at position 3, 7 and 12.	3.1	1	0	12alpha-hydroxy steroid; 3alpha-hydroxy steroid; 7alpha-hydroxy steroid; bile acid; C24-steroid; trihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
sitosterol, (3beta)-isomer Sobatum: tradename; active fraction of Solanum trilobatum; reduces side-effects of radiation-induced toxicity. sitosterol : A member of the class of phytosterols that is stigmast-5-ene substituted by a beta-hydroxy group at position 3.	3.15	5	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; C29-steroid; phytosterols; stigmastane sterol	anticholesteremic drug; antioxidant; mouse metabolite; plant metabolite; sterol methyltransferase inhibitor
cortisone [no description available]	1.95	1	0	11-oxo steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	human metabolite; mouse metabolite
4-allyl-2,6-dimethoxyphenol 4-allyl-2,6-dimethoxyphenol: structure in first source. 4-allyl-2,6-dimethoxyphenol : A member of the class of phenols that is phenol substituted by an allyl group at position 4 and methoxy groups at positions 2 and 6 respectively.	2.49	2	0	dimethoxybenzene; phenols; phenylpropanoid
5-hydroxymethylfurfural 5-hydroxymethylfurfural: has antisickling activity; HMF is the causative component in honey that affects the presystemic metabolism and pharmacokinetics of GZ in-vivo. 5-hydroxymethylfurfural : A member of the class of furans that is furan which is substituted at positions 2 and 5 by formyl and hydroxymethyl substituents, respectively. Virtually absent from fresh foods, it is naturally generated in sugar-containing foods during storage, and especially by drying or cooking. It is the causative component in honey that affects the presystemic metabolism and pharmacokinetics of GZ in-vivo.	8.79	10	0	arenecarbaldehyde; furans; primary alcohol	indicator; Maillard reaction product
5 alpha-androstane-3 beta,17 beta-diol 5alpha-androstane-3beta,17beta-diol : An androstane-3,17-diol that is 5alpha-androstane substituted by beta-hydroxy groups at positions 3 and 17. It is a metabolite of dihydrotestosterone.	3.1	1	0	17beta-hydroxy steroid; 3beta-hydroxy steroid; androstane-3,17-diol	Daphnia magna metabolite; human metabolite
cortol [no description available]	3.1	1	0	21-hydroxy steroid
lanosterol [no description available]	2.46	2	0	14alpha-methyl steroid; 3beta-sterol; tetracyclic triterpenoid	bacterial metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
21-hydroxypregnenolone 21-hydroxypregnenolone: RN given refers to (3beta)-isomer;. 21-hydroxypregnenolone : A hydroxypregnenolone that is pregnenolone which has been substituted by a hydroxy group at position 21.	3.1	1	0	21-hydroxy steroid; hydroxypregnenolone; primary alpha-hydroxy ketone	mouse metabolite
2-hydroxyestradiol 2-hydroxyestradiol: catechol estrogen; RN given refers to (17 beta)-isomer. 2-hydroxy-17beta-estradiol : A 2-hydroxy steroid that consists of 17beta-estradiol having an additional hydroxy group at position 2.	3.1	1	0	17beta-hydroxy steroid; 2-hydroxy steroid	carcinogenic agent; human metabolite; metabolite; mouse metabolite; prodrug
epietiocholanolone epietiocholanolone : A 3beta-hydroxy steroid that is 5beta-androstane substituted by a hydroxy group at position 3beta and an oxo group at position 17. It is a metabolite of testosterone.	3.1	1	0	17-oxo steroid; 3beta-hydroxy steroid; androstanoid	androgen; animal metabolite; human blood serum metabolite; mouse metabolite; rat metabolite
anisomycin Anisomycin: An antibiotic isolated from various Streptomyces species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system.. (-)-anisomycin : An antibiotic isolated from various Streptomyces species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system.	2.08	1	0	monohydroxypyrrolidine; organonitrogen heterocyclic antibiotic	anticoronaviral agent; antimicrobial agent; antineoplastic agent; antiparasitic agent; bacterial metabolite; DNA synthesis inhibitor; protein synthesis inhibitor
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	3.78	11	0
1-(2,4-Dihydroxyphenyl)-2-(4-methoxyphenyl)ethanone [no description available]	2.07	1	0	stilbenoid
lupeol [no description available]	7.99	4	0	pentacyclic triterpenoid; secondary alcohol	anti-inflammatory drug; plant metabolite
solanine Solanine: A mixture of alpha-chaconine and alpha-solanine, found in SOLANACEAE plants.. solanine : A glycoalkaloid poison found in species of the nightshade family (Solanaceae), such as the potato (Solanum tuberosum). It is a trisccharide derivative of solanidine [(22beta)-solanid-5-en-3beta-ol].	2.05	1	0
phenethicillin phenethicillin: minor descriptor (85); major descriptor (63-84); on-line search PENICILLIN, PHENOXYMETHYL/AA (66-85); Index Medicus search PHENETHICILLIN (63-84); RN given refers to (2S-(2alpha,5alpha,6beta))-isomer. phenethicillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-phenoxypropanamido group.	2.1	1	0	penicillin allergen; penicillin
methyl 3,4-dihydroxybenzoate [no description available]	2.48	2	0	catechols; methyl ester	antioxidant; neuroprotective agent; plant metabolite
acivicin [no description available]	1.99	1	0	isoxazoles; non-proteinogenic L-alpha-amino acid; organochlorine compound	antileishmanial agent; antimetabolite; antimicrobial agent; antineoplastic agent; EC 2.3.2.2 (gamma-glutamyltransferase) inhibitor; glutamine antagonist; metabolite
wortmannin [no description available]	3.43	7	0	acetate ester; cyclic ketone; delta-lactone; organic heteropentacyclic compound	anticoronaviral agent; antineoplastic agent; autophagy inhibitor; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor; geroprotector; Penicillium metabolite; radiosensitizing agent
medicarpin (-)-medicarpin : The (-)-enantiomer of medicarpin.	3.31	1	0	medicarpin	plant metabolite
3,4-dihydroxyphenylpropionic acid 3,4-dihydroxyphenylpropionic acid: metabolite of caffeic acid; RN given refers to parent cpd; structure. 3-(3,4-dihydroxyphenyl)propanoic acid : A monocarboxylic acid that is 3-phenylpropionic acid substituted by hydroxy groups at positions 3 and 4. Also known as dihydrocaffeic acid, it is a metabolite of caffeic acid and exhibits antioxidant activity.	2.93	4	0	(dihydroxyphenyl)propanoic acid	antioxidant; human xenobiotic metabolite
phyllanthin [no description available]	8.31	1	0	lignan
jatrorrhizine chloride [no description available]	2.07	1	0
8-deoxygartanin 8-deoxygartanin: a butyrylcholinesterase inhibitor; isolated from Garcinia mangostana; structure in first source	2.49	2	0	xanthones
crinine crinine: structure in first source	2.17	1	0	alkaloid
dihydropyridines Dihydropyridines: Pyridine moieties which are partially saturated by the addition of two hydrogen atoms in any position.	3.07	5	0
carboplatin [no description available]	7.31	1	0
lithium chloride Lithium Chloride: A salt of lithium that has been used experimentally as an immunomodulator.. lithium chloride : A metal chloride salt with a Li(+) counterion.	2.68	3	0	inorganic chloride; lithium salt	antimanic drug; geroprotector
s-adenosylhomocysteine S-Adenosylhomocysteine: 5'-S-(3-Amino-3-carboxypropyl)-5'-thioadenosine. Formed from S-adenosylmethionine after transmethylation reactions.. S-adenosyl-L-homocysteine : An organic sulfide that is the S-adenosyl derivative of L-homocysteine.	2.42	2	0	adenosines; amino acid zwitterion; homocysteine derivative; homocysteines; organic sulfide	cofactor; EC 2.1.1.72 [site-specific DNA-methyltransferase (adenine-specific)] inhibitor; EC 2.1.1.79 (cyclopropane-fatty-acyl-phospholipid synthase) inhibitor; epitope; fundamental metabolite
glycogen glycogen : A polydisperse, highly branched glucan composed of chains of D-glucopyranose residues in alpha(1->4) glycosidic linkage, joined together by alpha(1->6) glycosidic linkages. A small number of alpha(1->3) glycosidic linkages and some cumulative alpha(1->6) links also may occur. The branches in glycogen typically contain 8 to 12 glucose residues.	2.78	3	0
fibrin Fibrin: A protein derived from FIBRINOGEN in the presence of THROMBIN, which forms part of the blood clot.	8	4	0	peptide
bradykinin [no description available]	4.23	18	0	oligopeptide	human blood serum metabolite; vasodilator agent
hexacyanoferrate iii hexacyanoferrate III: RN given refers to parent cpd	2.41	2	0
glucosamine D-glucosamine : An amino sugar whose structure comprises D-glucose having an amino substituent at position 2.. 2-amino-2-deoxy-D-glucopyranose : A D-glucosamine whose structure comprises D-glucopyranose having an amino substituent at position 2.	2.31	1	0	D-glucosamine	Escherichia coli metabolite; geroprotector; mouse metabolite
polygalacturonic acid galacturonic acid: N1 same as NM; RN given refers to parent cpd with unspecified isomeric designation. D-galactopyranuronic acid : The pyranose form of D-galacturonic acid. D-galacturonic acid : The D-enantiomer of galacturonic acid. It is the main component of pectin.	2.21	1	0	D-galacturonic acid
carnosine polaprezinc: stimulates bone growth	7.1	1	0	amino acid zwitterion; dipeptide	anticonvulsant; antineoplastic agent; antioxidant; Daphnia magna metabolite; geroprotector; human metabolite; mouse metabolite; neuroprotective agent
naringenin (S)-naringenin : The (S)-enantiomer of naringenin.	11.22	17	0	(2S)-flavan-4-one; naringenin	expectorant; plant metabolite
epiglucan epiglucan: a highly side-chain/branched alkali-insoluble cell wall glucan from fungus such as Epicoccum nigrum, Botrytis cinerea, ascomycetes & basidiomycetes; also isolated S-4001 from Lei Wan (polyporus mylitiae), HA-beta-glucan from mushroom Pleutotus ostreatus (Fr.) Quel., and translam from seaweed Laminaria cichorioides; with commercially important functional properties including emulsification and friction reduction.	3.06	4	0
oxytocin Oxytocin: A nonapeptide hormone released from the neurohypophysis (PITUITARY GLAND, POSTERIOR). It differs from VASOPRESSIN by two amino acids at residues 3 and 8. Oxytocin acts on SMOOTH MUSCLE CELLS, such as causing UTERINE CONTRACTIONS and MILK EJECTION.. oxytocin : A cyclic nonapeptide hormone with amino acid sequence CYIQNCPLG that also acts as a neurotransmitter in the brain; the principal uterine-contracting and milk-ejecting hormone of the posterior pituitary. Together with the neuropeptide vasopressin, it is believed to influence social cognition and behaviour.	2.38	2	0	heterodetic cyclic peptide; peptide hormone	oxytocic; vasodilator agent
theanine theanine: RN given refers to (L)-isomer; precursor of ethylamine; found in green tea. N(5)-ethyl-L-glutamine : A N(5)-alkylglutamine where the alkyl group is ethyl. It has been isolated from green tea.	8.43	7	0	amino acid zwitterion; N(5)-alkyl-L-glutamine	geroprotector; neuroprotective agent; plant metabolite
3,4-dihydroxyphenyllactic acid 3,4-dihydroxyphenyllactic acid: from S. miltiorhiza Bge; dilates coronary artery; RN given refers to parent cpd without isomeric designation	2.61	2	0	2-hydroxy monocarboxylic acid; catechols
inositol 1,4,5-trisphosphate Inositol 1,4,5-Trisphosphate: Intracellular messenger formed by the action of phospholipase C on phosphatidylinositol 4,5-bisphosphate, which is one of the phospholipids that make up the cell membrane. Inositol 1,4,5-trisphosphate is released into the cytoplasm where it releases calcium ions from internal stores within the cell's endoplasmic reticulum. These calcium ions stimulate the activity of B kinase or calmodulin.	4.55	25	0	myo-inositol trisphosphate	mouse metabolite
ouabain Ouabain: A cardioactive glycoside consisting of rhamnose and ouabagenin, obtained from the seeds of Strophanthus gratus and other plants of the Apocynaceae; used like DIGITALIS. It is commonly used in cell biological studies as an inhibitor of the NA(+)-K(+)-EXCHANGING ATPASE.. cardiac glycoside : Steroid lactones containing sugar residues that act on the contractile force of the cardiac muscles.. ouabain : A steroid hormone that is a multi-hydroxylated alpha-L-rhamnosyl cardenoloide. It binds to and inhibits the plasma membrane Na(+)/K(+)-ATPase (sodium pump). It has been isolated naturally from Strophanthus gratus.	3.99	14	0	11alpha-hydroxy steroid; 14beta-hydroxy steroid; 5beta-hydroxy steroid; alpha-L-rhamnoside; cardenolide glycoside; steroid hormone	anti-arrhythmia drug; cardiotonic drug; EC 2.3.3.1 [citrate (Si)-synthase] inhibitor; EC 3.1.3.41 (4-nitrophenylphosphatase) inhibitor; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; ion transport inhibitor; plant metabolite
casein hydrolysate casein hydrolysate: an ingredient of trypticase soy broth; casitone is a tryptic digest of casein	2.13	1	0
taxifolin (+)-taxifolin : A taxifolin that has (2R,3R)-configuration.	3.46	7	0	taxifolin	metabolite
desmosterol Desmosterol: An intermediate in the synthesis of cholesterol.. desmosterol : A cholestanoid that is cholesta-5,24-diene substituted by a beta-hydroxy group at position 3. It is an intermediate metabolite obtained during the synthesis of cholesterol.	1.95	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; C27-steroid; cholestanoid	human metabolite; mouse metabolite
tosylphenylalanyl chloromethyl ketone Tosylphenylalanyl Chloromethyl Ketone: An inhibitor of Serine Endopeptidases. Acts as alkylating agent and is known to interfere with the translation process.. N-tosyl-L-phenylalanyl chloromethyl ketone : The N-tosyl derivative of L-phenylalanyl chloromethyl ketone.	1.97	1	0	alpha-chloroketone; sulfonamide	alkylating agent; serine proteinase inhibitor
tartaric acid tartaric acid: RN given refers to cpd with unspecified isomeric designation. D-tartaric acid : The D-enantiomer of tartaric acid.	2.74	3	0	tartaric acid	Escherichia coli metabolite
n-formylmethionine N-formyl-L-methionine : A L-methionine derivative in which one of the hydrogens attached to the nitrogen is replaced by a formyl group.	2.36	2	0	L-methionine derivative; N-formyl amino acid; proteinogenic amino acid	metabolite
protochlorophyllide Protochlorophyllide: A photo-active pigment localized in prolamellar bodies occurring within the proplastids of dark-grown bean leaves. In the process of photoconversion, the highly fluorescent protochlorophyllide is converted to chlorophyll.. protochlorophyllide : An analogue of chlorophyll that lacks the phytol side-chain. The parent of the protochlorophyllide class.	2.11	1	0
nitroarginine Nitroarginine: An inhibitor of nitric oxide synthetase which has been shown to prevent glutamate toxicity. Nitroarginine has been experimentally tested for its ability to prevent ammonia toxicity and ammonia-induced alterations in brain energy and ammonia metabolites. (Neurochem Res 1995:200(4):451-6). N(gamma)-nitro-L-arginine : An L-arginine derivative that is L-arginine in which the terminal nitrogen of the guanidyl group is replaced by a nitro group.	1.99	1	0	guanidines; L-arginine derivative; N-nitro compound; non-proteinogenic L-alpha-amino acid
inositol 3-phosphate inositol 3-phosphate: RN given refers to (myo)-isomer	1.98	1	0
1,2,6-tri-o-galloyl-beta-d-glucopyranose 1,2,6-tri-O-galloyl-beta-D-glucopyranose: from Terminalia chebula fruits, effective against multidrug-resistant uropathogens; structure in first source. 1,2,6-tris-O-galloyl-beta-D-glucose : A galloyl-beta-D-glucose compound having the galloyl groups in the 1-, 2- and 6-positions.	2	1	0	gallate ester; galloyl beta-D-glucose
2-hydroxyestrone 2-hydroxyestrone: catechol estrogen which is a major metabolite of estradiol in man & animals; RN given refers to parent cpd. 2-hydroxyestrone : A 2-hydroxy steroid that is estrone substituted by a hydroxy group at position 2.	3.1	1	0	2-hydroxy steroid; catechols	human metabolite
eriodictyol eriodictyol: structure. eriodictyol : A tetrahydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5, 7, 3' and 4' respectively.	3.94	3	0	3'-hydroxyflavanones; tetrahydroxyflavanone
pelargonidin pelargonidin: influences flower phenotype. pelargonidin : An anthocyanidin cation that is flavylium substituted by a hydroxy groups at positions 3, 5, 7 and 4'.	2.25	1	0	5-hydroxyanthocyanidin	plant metabolite
(+)-limonene (4R)-limonene : An optically active form of limonene having (4R)-configuration.	2.01	1	0	limonene	plant metabolite
arbutin hydroquinone O-beta-D-glucopyranoside : A monosaccharide derivative that is hydroquinone attached to a beta-D-glucopyranosyl residue at position 4 via a glycosidic linkage.	4.86	10	0	beta-D-glucoside; monosaccharide derivative	Escherichia coli metabolite; plant metabolite
cellulase Cellulase: An endocellulase with specificity for the hydrolysis of 1,4-beta-glucosidic linkages in CELLULOSE, lichenin, and cereal beta-glucans.. beta-cellotriose : A cellotriose with a beta-configuration at the anomeric position.	2.83	3	0	cellotriose
strychnine Strychnine: An alkaloid found in the seeds of STRYCHNOS NUX-VOMICA. It is a competitive antagonist at glycine receptors and thus a convulsant. It has been used as an analeptic, in the treatment of nonketotic hyperglycinemia and sleep apnea, and as a rat poison.. strychnine : A monoterpenoid indole alkaloid that is strychnidine bearing a keto substituent at the 10-position.	2.39	2	0	monoterpenoid indole alkaloid; organic heteroheptacyclic compound	avicide; cholinergic antagonist; glycine receptor antagonist; neurotransmitter agent; rodenticide
quinidine Quinidine: An optical isomer of quinine, extracted from the bark of the CHINCHONA tree and similar plant species. This alkaloid dampens the excitability of cardiac and skeletal muscles by blocking sodium and potassium currents across cellular membranes. It prolongs cellular ACTION POTENTIALS, and decreases automaticity. Quinidine also blocks muscarinic and alpha-adrenergic neurotransmission.. quinidine : A cinchona alkaloid consisting of cinchonine with the hydrogen at the 6-position of the quinoline ring substituted by methoxy.	2.89	4	0	cinchona alkaloid	alpha-adrenergic antagonist; anti-arrhythmia drug; antimalarial; drug allergen; EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor; EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor; muscarinic antagonist; P450 inhibitor; potassium channel blocker; sodium channel blocker
monensin Monensin: An antiprotozoal agent produced by Streptomyces cinnamonensis. It exerts its effect during the development of first-generation trophozoites into first-generation schizonts within the intestinal epithelial cells. It does not interfere with hosts' development of acquired immunity to the majority of coccidial species. Monensin is a sodium and proton selective ionophore and is widely used as such in biochemical studies.. monensin A : A spiroketal, monensin A is the major component of monensin, a mixture of antibiotic substances produced by Streptomyces cinnamonensis. An antiprotozoal, it is used as the sodium salt as a feed additive for the prevention of coccidiosis in poultry and as a growth promoter in cattle.	3.36	7	0	cyclic hemiketal; monocarboxylic acid; polyether antibiotic; spiroketal	antifungal agent; coccidiostat; ionophore
epiandrosterone epiandrosterone : A 3beta-hydroxy steroid that is (5alpha)-androstane substituted by a beta-hydroxy group at position 3 and an oxo group at position 17.	3.1	1	0	17-oxo steroid; 3beta-hydroxy steroid; androstanoid	androgen; human metabolite
netilmicin Netilmicin: Semisynthetic 1-N-ethyl derivative of SISOMYCIN, an aminoglycoside antibiotic with action similar to gentamicin, but less ear and kidney toxicity.	2	1	0
norpseudoephedrine norpseudoephedrine: major metabolite of diethylpropion in man under acidic urine conditions; RN given refers to cpd without isomeric designation;. cathine : An amphetamine that is propylbenzene substituted by a hydroxy group at position 1 and by an amino group at position 2 (the 1S,2S-stereoisomer).	2.1	1	0	amphetamines; phenethylamine alkaloid	central nervous system stimulant; plant metabolite; psychotropic drug
cyanidin 3-o-beta-d-glucopyranoside cyanidin 3-O-beta-D-glucoside : An anthocyanin cation that is a cyanidin cation linked to a beta-D-glucosyl moiety at position 3.	3.27	1	0	anthocyanin cation; beta-D-glucoside; monosaccharide derivative	metabolite
euphol euphol: from Euphorbia acaulis Roxb.; structure given in first source	2.03	1	0	triterpenoid
ryanodine Ryanodine: A methylpyrrole-carboxylate from RYANIA that disrupts the RYANODINE RECEPTOR CALCIUM RELEASE CHANNEL to modify CALCIUM release from SARCOPLASMIC RETICULUM resulting in alteration of MUSCLE CONTRACTION. It was previously used in INSECTICIDES. It is used experimentally in conjunction with THAPSIGARGIN and other inhibitors of CALCIUM ATPASE uptake of calcium into SARCOPLASMIC RETICULUM.. ryanodine : An insecticide alkaloid isolated from South American plant Ryania speciosa.	4.55	25	0
peonidin peonidin: a COX-2 inhibitor with protein kinase inhibitory and phytogenic antineoplastic activities; RN given for chloride salt. peonidin : An anthocyanidin cation that is flavylium bearing four hydroxy substituents at positions 3, 4', 5 and 7 as well as a methoxy substituent at position 3'.	2.25	1	0	5-hydroxyanthocyanidin	antineoplastic agent; antioxidant; apoptosis inducer; metabolite
biflorin biflorin: isolated from Capraria biflora; structure in first source	1.99	1	0	chromones
columbin columbin: from Tinospora Cordifolia Miers & Calumbae Radix (the root of Jateorhiza columba MIERS, Menispermacea) ; structure given in first source	2.6	1	0	organic heterotricyclic compound; organooxygen compound
stevioside stevioside: Kaurene glucoside from leaves of Stevia rebaudiana; 300 times as sweet as sugar. stevioside : A diterpene glycoside that is rubusoside in which the hydroxy group at position 2 of the allylic beta-D-glucoside has been converted to the corresponding beta-D-glucoside. It is a natural herbal sweetener that is 250-300 times sweeter than sucrose (though with a bitter aftertaste), extracted from the Stevia rebaudiana plant native to South America.. diterpene glycoside : A terpene glycoside in which the terpene moiety is a diterpenoid.	2.41	1	0	beta-D-glucoside; bridged compound; diterpene glycoside; ent-kaurane diterpenoid; tetracyclic diterpenoid	anti-inflammatory agent; antineoplastic agent; antioxidant; hypoglycemic agent; plant metabolite; sweetening agent
afzelechin afzelechin: from Hovenia dulcis; structure in first source. afzelechin : A tetrahydroxyflavan that is (2S)-flavan substituted by hydroxy groups at positions 3, 5, 7 and 4' respectively.	2.17	1	0	catechin; tetrahydroxyflavan	EC 3.2.1.20 (alpha-glucosidase) inhibitor; plant metabolite
micheliolide micheliolide: has antineoplastic activity; structure in first source	2.17	1	0	sesquiterpene lactone
farrerol farrerol: expectorant principle isolated from leaves of Rhododendron dauricum L; structure	2.11	1	0	organic molecular entity	metabolite
naringin [no description available]	4.66	8	0	(2S)-flavan-4-one; 4'-hydroxyflavanones; dihydroxyflavanone; disaccharide derivative; neohesperidoside	anti-inflammatory agent; antineoplastic agent; metabolite
ochratoxin a ochratoxin A: structure in first source & in Merck, 9th ed, #6549. ochratoxin A : A phenylalanine derivative resulting from the formal condensation of the amino group of L-phenylalanine with the carboxy group of (3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carboxylic acid (ochratoxin alpha). It is among the most widely occurring food-contaminating mycotoxins, produced by Aspergillus ochraceus, Aspergillus carbonarius and Penicillium verrucosum.	7.77	3	0	isochromanes; monocarboxylic acid amide; N-acyl-L-phenylalanine; organochlorine compound; phenylalanine derivative	Aspergillus metabolite; calcium channel blocker; carcinogenic agent; mycotoxin; nephrotoxin; Penicillium metabolite; teratogenic agent
theasinensin a theasinensin A: a tea polyphenol formed from (-)-epigallocatechin gallate, suppresses antibiotic resistance of methicillin-resistant Staphylococcus aureus. theasinensin A : A biflavonoid that is obtained by coupling of two molecules of (-)-epigallocatechin 3-gallate resulting in a bond between positions C-2 of the hydroxyphenyl ring. It is a natural product found in oolong tea.	2.95	4	0	biflavonoid; gallate ester; proanthocyanidin	anti-inflammatory agent; anticoronaviral agent; apoptosis inducer; EC 3.2.1.20 (alpha-glucosidase) inhibitor; hepatoprotective agent; hypoglycemic agent; melanin synthesis inhibitor; plant metabolite
vicenin ii vicenin: isolated from the leaves of the Indian plant Ocimum sanctum were tested for their radioprotective effect in mice. isovitexin 8-C-beta-glucoside : A C-glycosyl compound that is isovitexin in which the hydrogen at position 8 is replaced by a beta-D-glucosyl residue.	2.17	1	0	C-glycosyl compound; trihydroxyflavone	metabolite
casuarinin casuarinin: a hydrolyzable tannin from the bark of Terminalia arjuna (Combretaceae)	2.31	1	0	tannin
Chebulagic acid [no description available]	2.42	2	0	tannin
eugeniin eugeniin: structure in first source. eugeniin : An ellagitannin isolated from the dried flower buds of Eugenia caryophyllata. It exhibits alpha-glucosidase inhibitory activity and antiviral activity against acyclovir and phosphonoacetic acid (PAA)-resistant herpes simplex virus type 1 (HSV-1) as well as the wild-type HSV-1.	4.81	10	0	beta-D-glucoside; ellagitannin; gallate ester; lactone	anti-HSV-1 agent; antifungal agent; antineoplastic agent; EC 3.2.1.20 (alpha-glucosidase) inhibitor; metabolite
Pedunculagin pedunculagin: from the walnut (Juglans regia) pellicle	2	1	0	tannin
tellimagrandin i tellimagrandin I: isolated from Filipendula palmata; RN given for (D)-isomer	5.54	21	0	tannin
chrysophanol 8-o-glucoside chrysophanol 8-O-glucoside: has anti-hepatitis B virus activity; also has antiplatelet and anticoagulant activities; isolated from Rheum palmatum. chrysophanol 8-O-beta-D-glucoside : A beta-D-glucoside in which the aglycone species is chrysophanol, the glycosidic linkage being to the hydroxy group at C-8.	2	1	0	beta-D-glucoside; monohydroxyanthraquinone
gingerol gingerol: an active ingredient in GINGER along with SHOGAOL. a nonvolatile methoxy phenyl decanone. gingerol : A beta-hydroxy ketone that is 5-hydroxydecan-3-one substituted by a 4-hydroxy-3-methoxyphenyl moiety at position 1; believed to inhibit adipogenesis. It is a constituent of fresh ginger.	2.21	1	0	beta-hydroxy ketone; guaiacols	antineoplastic agent; plant metabolite
alpha-chaconine alpha-chaconine: glycoside of solanidine; structure in 5th source	7.05	1	0	glycoalkaloid; steroid saponin
theogallin theogallin: structure in first source. theogallin : A gallate ester resulting from the formal condensation of gallic acid with the (5R)-hydroxy group of (-)-quinic acid (i.e. the hydroxy group on the same side of the cyclohexane ring as the carboxy group).	3.16	5	0	gallate ester; monocarboxylic acid; tertiary alcohol
lignans Lignans: A class of dibenzylbutane derivatives which occurs in higher plants and in fluids (bile, serum, urine, etc.) in man and other animals. These compounds, which have a potential anti-cancer role, can be synthesized in vitro by human fecal flora. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)	5.13	13	0
1-alpha-terpineol (S)-(-)-alpha-terpineol : The (S)-enantiomer of alpha-terpineol.	3.1	1	0	alpha-terpineol	plant metabolite
n-formylmethionine leucyl-phenylalanine N-Formylmethionine Leucyl-Phenylalanine: A formylated tripeptide originally isolated from bacterial filtrates that is positively chemotactic to polymorphonuclear leucocytes, and causes them to release lysosomal enzymes and become metabolically activated.. N-formyl-L-methionyl-L-leucyl-L-phenylalanine : A tripeptide composed of L-Met, L-Leu and L-Phe in a linear sequence with a formyl group at the amino terminus. It acts as a potent inducer of leucocyte chemotaxis and macrophage activator as well as a ligand for the FPR receptor.	3.67	10	0	tripeptide
diprenorphine Diprenorphine: A narcotic antagonist similar in action to NALOXONE. It is used to remobilize animals after ETORPHINE neuroleptanalgesia and is considered a specific antagonist to etorphine.	3.1	1	0	morphinane alkaloid
sodium arsenite sodium arsenite : An inoganic sodium salt with formula with formula NaAsO2.	2.66	2	0	arsenic molecular entity; inorganic sodium salt	antibacterial agent; antifungal agent; antineoplastic agent; carcinogenic agent; herbicide; insecticide; rodenticide
epiafzelechin epiafzelechin: antioxidant; 3'-deoxy form of epicatechin; structure in first source. (-)-epiafzelechin : A catechin derivative having (2R,3R)-configuration.	2.17	1	0	catechin	plant metabolite
petunidin-3-glucoside [no description available]	2.25	1	0	anthocyanin cation; aromatic ether; beta-D-glucoside	antioxidant; metabolite
malvidin-3-glucoside malvidin 3-O-beta-D-glucoside : An anthocyanin cation consisting of malvidin having a beta-D-glucosyl residue attached at the 3-hydroxy position.	3.19	5	0	anthocyanin cation; aromatic ether; beta-D-glucoside	metabolite
pancracine pancracine: structure in first source	2.17	1	0	isoquinoline alkaloid fundamental parent; isoquinoline alkaloid
tolterodine [no description available]	2.1	1	0	tertiary amine	antispasmodic drug; muscarinic antagonist; muscle relaxant
vinpocetine vinpocetine: whole issue of Arzneim Forsch (23 articles) discuss this drug; Arzneim Forsch 26(10a);1976; RN given refers to parent cpd with unspecified isomeric designation	2.1	1	0	alkaloid	geroprotector
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	3.54	7	0	cyclodextrin
acarbose [no description available]	2.07	1	0	amino cyclitol; glycoside
e-z cinnamic acid cinnamic acid : A monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia.. trans-cinnamic acid : The E (trans) isomer of cinnamic acid	5.98	32	0	cinnamic acid	plant metabolite
ergosterol [no description available]	4.28	5	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; ergostanoid; phytosterols	fungal metabolite; Saccharomyces cerevisiae metabolite
tretinoin Tretinoin: An important regulator of GENE EXPRESSION during growth and development, and in NEOPLASMS. Tretinoin, also known as retinoic acid and derived from maternal VITAMIN A, is essential for normal GROWTH; and EMBRYONIC DEVELOPMENT. An excess of tretinoin can be teratogenic. It is used in the treatment of PSORIASIS; ACNE VULGARIS; and several other SKIN DISEASES. It has also been approved for use in promyelocytic leukemia (LEUKEMIA, PROMYELOCYTIC, ACUTE).. retinoic acid : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraenoic acid substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).. all-trans-retinoic acid : A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry.	3.76	3	0	retinoic acid; vitamin A	anti-inflammatory agent; antineoplastic agent; antioxidant; AP-1 antagonist; human metabolite; keratolytic drug; retinoic acid receptor agonist; retinoid X receptor agonist; signalling molecule
arachidonic acid icosa-5,8,11,14-tetraenoic acid : Any icosatetraenoic acid with the double bonds at positions 5, 8, 11 and 14.. arachidonate : A long-chain fatty acid anion resulting from the removal of a proton from the carboxy group of arachidonic acid.	6.28	36	1	icosa-5,8,11,14-tetraenoic acid; long-chain fatty acid; omega-6 fatty acid	Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite; mouse metabolite
alpha-cyclodextrin alpha-cyclodextrin : A cycloamylose composed of six alpha-(1->4) linked D-glucopyranose units.	2.21	1	0	cyclodextrin
fumaric acid fumaric acid: see also record for ferrous fumarate; use FUMARATES for general fumaric acid esters. fumaric acid : A butenedioic acid in which the C=C double bond has E geometry. It is an intermediate metabolite in the citric acid cycle.	4.04	4	0	butenedioic acid	food acidity regulator; fundamental metabolite; geroprotector
farnesol Farnesol: A colorless liquid extracted from oils of plants such as citronella, neroli, cyclamen, and tuberose. It is an intermediate step in the biological synthesis of cholesterol from mevalonic acid in vertebrates. It has a delicate odor and is used in perfumery. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). (2-trans,6-trans)-farnesol : The (2-trans,6-trans)-stereoisomer of farnesol.. farnesol : A farnesane sesquiterpenoid that is dodeca-2,6,10-triene substituted by methyl groups at positions 3, 7 and 11 and a hydroxy group at position 1.	2	1	0	farnesol	plant metabolite
resveratrol trans-resveratrol : A resveratrol in which the double bond has E configuration.	7.42	44	0	resveratrol	antioxidant; phytoalexin; plant metabolite; quorum sensing inhibitor; radical scavenger
retinol Vitamin A: Retinol and derivatives of retinol that play an essential role in metabolic functioning of the retina, the growth of and differentiation of epithelial tissue, the growth of bone, reproduction, and the immune response. Dietary vitamin A is derived from a variety of CAROTENOIDS found in plants. It is enriched in the liver, egg yolks, and the fat component of dairy products.. vitamin A : Any member of a group of fat-soluble retinoids produced via metabolism of provitamin A carotenoids that exhibit biological activity against vitamin A deficiency. Vitamin A is involved in immune function, vision, reproduction, and cellular communication.. all-trans-retinol : A retinol in which all four exocyclic double bonds have E- (trans-) geometry.. retinol : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraen-1-ol substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).	4.38	6	0	retinol; vitamin A	human metabolite; mouse metabolite; plant metabolite
oleic acid Oleic Acid: An unsaturated fatty acid that is the most widely distributed and abundant fatty acid in nature. It is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. (Stedman, 26th ed). oleic acid : An octadec-9-enoic acid in which the double bond at C-9 has Z (cis) stereochemistry.	8.97	13	0	octadec-9-enoic acid	antioxidant; Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; Escherichia coli metabolite; mouse metabolite; plant metabolite; solvent
tacrolimus Tacrolimus: A macrolide isolated from the culture broth of a strain of Streptomyces tsukubaensis that has strong immunosuppressive activity in vivo and prevents the activation of T-lymphocytes in response to antigenic or mitogenic stimulation in vitro.. tacrolimus (anhydrous) : A macrolide lactam containing a 23-membered lactone ring, originally isolated from the fermentation broth of a Japanese soil sample that contained the bacteria Streptomyces tsukubaensis.	8.03	4	0	macrolide lactam	bacterial metabolite; immunosuppressive agent
ferulic acid ferulate : A monocarboxylic acid anion obtained by the deprotonation of the carboxy group of ferulic acid.	10.65	133	1	ferulic acids	anti-inflammatory agent; antioxidant; apoptosis inhibitor; cardioprotective agent; MALDI matrix material; plant metabolite
pectins Pectins: High molecular weight polysaccharides present in the cell walls of all plants. Pectins cement cell walls together. They are used as emulsifiers and stabilizers in the food industry. They have been tried for a variety of therapeutic uses including as antidiarrheals, where they are now generally considered ineffective, and in the treatment of hypercholesterolemia.. alpha-D-galacturonic acid : The alpha-anomer of D-galacturonic acid.	9	12	0	D-galactopyranuronic acid
cocaine Cocaine: An alkaloid ester extracted from the leaves of plants including coca. It is a local anesthetic and vasoconstrictor and is clinically used for that purpose, particularly in the eye, ear, nose, and throat. It also has powerful central nervous system effects similar to the amphetamines and is a drug of abuse. Cocaine, like amphetamines, acts by multiple mechanisms on brain catecholaminergic neurons; the mechanism of its reinforcing effects is thought to involve inhibition of dopamine uptake.. cocaine : A tropane alkaloid obtained from leaves of the South American shrub Erythroxylon coca.	2.57	2	0	benzoate ester; methyl ester; tertiary amino compound; tropane alkaloid	adrenergic uptake inhibitor; central nervous system stimulant; dopamine uptake inhibitor; environmental contaminant; local anaesthetic; mouse metabolite; plant metabolite; serotonin uptake inhibitor; sodium channel blocker; sympathomimetic agent; vasoconstrictor agent; xenobiotic
eicosapentaenoic acid icosapentaenoic acid : Any straight-chain, C20 polyunsaturated fatty acid having five C=C double bonds.. all-cis-5,8,11,14,17-icosapentaenoic acid : An icosapentaenoic acid having five cis-double bonds at positions 5, 8, 11, 14 and 17.	2.8	3	0	icosapentaenoic acid; omega-3 fatty acid	anticholesteremic drug; antidepressant; antineoplastic agent; Daphnia galeata metabolite; fungal metabolite; micronutrient; mouse metabolite; nutraceutical
alpha-methyl-4-carboxyphenylglycine alpha-methyl-4-carboxyphenylglycine: glutamate receptor antagonist. (S)-alpha-methyl-4-carboxyphenylglycine : A non-proteinogenic alpha-amino acid that is alanine in which the alpha-hydrogen is replaced by a 4-carboxyphenyl group (the S-enantiomer). It is a non-selective group I/group II metabotropic glutamate receptor (mGluR) antagonist.	2	1	0	non-proteinogenic alpha-amino acid	metabotropic glutamate receptor antagonist
thapsigargin Thapsigargin: A sesquiterpene lactone found in roots of THAPSIA. It inhibits SARCOPLASMIC RETICULUM CALCIUM-TRANSPORTING ATPASES.. thapsigargin : An organic heterotricyclic compound that is a hexa-oxygenated 6,7-guaianolide isolated fron the roots of Thapsia garganica L., Apiaceae. A potent skin irritant, it is used in traditional medicine as a counter-irritant. Thapsigargin inhibits Ca(2+)-transporting ATPase mediated uptake of calcium ions into sarcoplasmic reticulum and is used in experimentation examining the impacts of increasing cytosolic calcium concentrations.	4.7	29	0	butyrate ester; organic heterotricyclic compound; sesquiterpene lactone	calcium channel blocker; EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor
mycophenolic acid Mycophenolic Acid: Compound derived from Penicillium stoloniferum and related species. It blocks de novo biosynthesis of purine nucleotides by inhibition of the enzyme inosine monophosphate dehydrogenase (IMP DEHYDROGENASE). Mycophenolic acid exerts selective effects on the immune system in which it prevents the proliferation of T-CELLS, LYMPHOCYTES, and the formation of antibodies from B-CELLS. It may also inhibit recruitment of LEUKOCYTES to sites of INFLAMMATION.. mycophenolate : A monocarboxylic acid anion resulting from the removal of a proton from the carboxy group of mycophenolic acid.. mycophenolic acid : A member of the class of 2-benzofurans that is 2-benzofuran-1(3H)-one which is substituted at positions 4, 5, 6, and 7 by methyl, methoxy, (2E)-5-carboxy-3-methylpent-2-en-1-yl, and hydroxy groups, respectively. It is an antibiotic produced by Penicillium brevi-compactum, P. stoloniferum, P. echinulatum and related species. An immunosuppressant, it is widely used (partiularly as its sodium salt and as the 2-(morpholin-4-yl)ethyl ester prodrug, mycophenolate mofetil) to prevent tissue rejection following organ transplants and for the treatment of certain autoimmune diseases.	3.51	2	0	2-benzofurans; gamma-lactone; monocarboxylic acid; phenols	anticoronaviral agent; antimicrobial agent; antineoplastic agent; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; environmental contaminant; immunosuppressive agent; mycotoxin; Penicillium metabolite; xenobiotic
mupirocin Mupirocin: A topically used antibiotic from a strain of Pseudomonas fluorescens. It has shown excellent activity against gram-positive staphylococci and streptococci. The antibiotic is used primarily for the treatment of primary and secondary skin disorders, nasal infections, and wound healing.. mupirocin : An alpha,beta-unsaturated ester resulting from the formal condensation of the alcoholic hydroxy group of 9-hydroxynonanoic acid with the carboxy group of (2E)-4-[(2S)-tetrahydro-2H-pyran-2-yl]-3-methylbut-2-enoic acid in which the tetrahydropyranyl ring is substituted at positions 3 and 4 by hydroxy groups and at position 5 by a {(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl}methyl group. Originally isolated from the Gram-negative bacterium Pseudomonas fluorescens, it is used as a topical antibiotic for the treatment of Gram-positive bacterial infections.	2.05	1	0	alpha,beta-unsaturated carboxylic ester; epoxide; monocarboxylic acid; oxanes; secondary alcohol; triol	antibacterial drug; bacterial metabolite; protein synthesis inhibitor
lycopene [no description available]	2.47	2	0	acyclic carotene	antioxidant; plant metabolite
y 27632 Y 27632: RN given for di-HCl salt; inhibits Rho-associated protein kinase; inhibits calcium sensitization to affect smooth muscle relaxation; structure in first source. Y-27632 : A monocarboxylic acid amide that is trans-[(1R)-1-aminoethyl]cyclohexanecarboxamide in which one of the nitrogens of the aminocarbony group is substituted by a pyridine nucleus. It has been shown to exhibit inhibitory activity against Rho-associated protein kinase (ROCK) enzyme.	2.73	3	0	aromatic amide
prostaglandin d2 Prostaglandin D2: The principal cyclooxygenase metabolite of arachidonic acid. It is released upon activation of mast cells and is also synthesized by alveolar macrophages. Among its many biological actions, the most important are its bronchoconstrictor, platelet-activating-factor-inhibitory, and cytotoxic effects.. prostaglandin D2 : A member of the class of prostaglandins D that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9 and 15 and an oxo group at position 11 (the 5Z,9alpha,13E,15S- stereoisomer).	2.9	4	0	prostaglandins D	human metabolite; mouse metabolite
diethylstilbestrol Diethylstilbestrol: A synthetic nonsteroidal estrogen used in the treatment of menopausal and postmenopausal disorders. It was also used formerly as a growth promoter in animals. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), diethylstilbestrol has been listed as a known carcinogen. (Merck, 11th ed). diethylstilbestrol : An olefinic compound that is trans-hex-3-ene in which the hydrogens at positions 3 and 4 have been replaced by p-hydroxyphenyl groups.	3.1	1	0	olefinic compound; polyphenol	antifungal agent; antineoplastic agent; autophagy inducer; calcium channel blocker; carcinogenic agent; EC 1.1.1.146 (11beta-hydroxysteroid dehydrogenase) inhibitor; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; endocrine disruptor; xenoestrogen
h 89 N-(2-(4-bromocinnamylamino)ethyl)-5-isoquinolinesulfonamide: structure given in first source. N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide : A member of the class of isoquinolines that is the sulfonamide obtained by formal condensation of the sulfo group of isoquinoline-5-sulfonic acid with the primary amino group of N(1)-[3-(4-bromophenyl)prop-2-en-1-yl]ethane-1,2-diamine. It is a protein kinase A inhibitor.. (E)-N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide : A N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide in which the double bond adopts a trans-configuration.	2.1	1	0	N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide
3-hydroxyhippuric acid 3-hydroxyhippuric acid: a kynureninase inhibitor; structure in first source. m-hydroxyhippuric acid : An N-acylglycine that is hippuric acid (N-benzoylglycine) substituted at position 3 on the phenyl ring by a hydroxy group.	3.46	1	1	N-acylglycine; phenols	metabolite
1,3,6-tri-o-galloyl-beta-d-glucose 1,3,6-tri-O-galloylglucose: structure in first source	4.06	4	0
iridoids Iridoids: A type of MONOTERPENES, derived from geraniol. They have the general form of cyclopentanopyran, but in some cases, one of the rings is broken as in the case of secoiridoid. They are different from the similarly named iridals (TRITERPENES).	3.54	8	0
kt 5720 KT 5720: indolocarbazole; synthetic derivative of K 252a. KT 5720 : An organic heterooctacyclic compound that is 1H,1'H-2,2'-biindole in which the nitrogens have undergone formal oxidative coupling to positions 2 and 5 of hexyl (3S)-3-hydroxy-2-methyltetrahydrofuran-3-carboxylate (the 2R,3S,5S product), and in which the 3 and 3' positions of the biindole moiety have also undergone formal oxidative coupling to positions 3 and 4 of 1,5-dihydro-2H-pyrrol-2-one.	2.01	1	0	carboxylic ester; gamma-lactam; hemiaminal; indolocarbazole; organic heterooctacyclic compound; semisynthetic derivative; tertiary alcohol	EC 2.7.11.11 (cAMP-dependent protein kinase) inhibitor
cefamandole Cefamandole: Semisynthetic wide-spectrum cephalosporin with prolonged action, probably due to beta-lactamase resistance. It is used also as the nafate.. cefamandole : A cephalosporin compound having (R)-mandelamido and N-methylthiotetrazole side-groups.	2.1	1	0	cephalosporin; semisynthetic derivative	antibacterial drug
dactinomycin Dactinomycin: A compound composed of a two CYCLIC PEPTIDES attached to a phenoxazine that is derived from STREPTOMYCES parvullus. It binds to DNA and inhibits RNA synthesis (transcription), with chain elongation more sensitive than initiation, termination, or release. As a result of impaired mRNA production, protein synthesis also declines after dactinomycin therapy. (From AMA Drug Evaluations Annual, 1993, p2015)	2.95	4	0	actinomycin	mutagen
gamma-sitosterol clionasterol : A member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3.	4.41	20	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; phytosterols	marine metabolite; plant metabolite
melphalan Melphalan: An alkylating nitrogen mustard that is used as an antineoplastic in the form of the levo isomer - MELPHALAN, the racemic mixture - MERPHALAN, and the dextro isomer - MEDPHALAN; toxic to bone marrow, but little vesicant action; potential carcinogen.. melphalan : A phenylalanine derivative comprising L-phenylalanine having [bis(2-chloroethyl)amino group at the 4-position on the phenyl ring.	1.94	1	0	L-phenylalanine derivative; nitrogen mustard; non-proteinogenic L-alpha-amino acid; organochlorine compound	alkylating agent; antineoplastic agent; carcinogenic agent; drug allergen; immunosuppressive agent
tenofovir tenofovir (anhydrous) : A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens is replaced by a [(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(isopropyloxycarbonyloxymethyl) ester (disoproxil ester) prodrug is used as the fumaric acid salt in combination therapy for the treatment of HIV infection.	2.11	1	0	nucleoside analogue; phosphonic acids	antiviral drug; drug metabolite; HIV-1 reverse transcriptase inhibitor
Epigallocatechin 3,5-Digallate [no description available]	2.05	1	0	catechin
euscaphic acid euscaphic acid: isolated from medicinal plant, Euscaphis japonica Pax.; structure; RN given refers to 2alpha,3alpha-isomer. euscaphic acid : A pentacyclic triterpenoid that is urs-12-en-28-oic acid substituted by hydroxy groups at positions 2, 3 and 19 respectively (the 2alpha,3alpha-stereoisomer). It has been isolated from the leaves of Rosa laevigata.	2.1	1	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid; triol	plant metabolite
cinnamtannin b-1 cinnamtannin B-1: COX2 Inhibitor from bay wood and bark of Cinnamomum cassia; structure in second source. cinnamtannin B-1 : A proanthocyanidin found in Cinnamomum cassia and Cinnamomum zeylanicum.	2.11	1	0	proanthocyanidin	cyclooxygenase 2 inhibitor; plant metabolite
pentyl gallate pentyl gallate: food and pharmaceutical antioxidant with ability of electron-donating; structure in first source	3.57	8	0
morolic acid morolic acid: from Pistacia terebinthus galls; structure in first source	2.11	1	0
riboflavin vitamin B2 : Any member of a group of vitamers that belong to the chemical structural class called flavins that exhibit biological activity against vitamin B2 deficiency. Symptoms associated with vitamin B2 deficiency include glossitis, seborrhea, angular stomaitis, cheilosis and photophobia. The vitamers include riboflavin and its phosphate derivatives (and includes their salt, ionised and hydrate forms).	2.75	3	0	flavin; vitamin B2	anti-inflammatory agent; antioxidant; cofactor; Escherichia coli metabolite; food colouring; fundamental metabolite; human urinary metabolite; mouse metabolite; photosensitizing agent; plant metabolite
laninamivir laninamivir: an antiviral agent	2.1	1	0	acetamides
likviriton liquiritin: isoalted from Glycyrrhizae radix. liquiritin : A flavanone glycoside that is liquiritigenin attached to a beta-D-glucopyranosyl residue at position 4' via a glycosidic linkage.	2.53	2	0	beta-D-glucoside; flavanone glycoside; monohydroxyflavanone; monosaccharide derivative	anti-inflammatory agent; anticoronaviral agent; plant metabolite
sodium bicarbonate Sodium Bicarbonate: A white, crystalline powder that is commonly used as a pH buffering agent, an electrolyte replenisher, systemic alkalizer and in topical cleansing solutions.	2.21	1	0	one-carbon compound; organic sodium salt	antacid; food anticaking agent
potassium bicarbonate potassium hydrogencarbonate : A potassium salt that is the monopotassium salt of carbonic acid. It has fungicidal properties and is used in organic farming for the control of powdery mildew and apple scab.	2.05	1	0	organic salt; potassium salt	antifungal agrochemical; buffer; food acidity regulator; raising agent
potassium acetate Potassium Acetate: A potassium salt used to replenish ELECTROLYTES, for restoration of WATER-ELECTROLYTE BALANCE, as well as a urinary and systemic alkalizer, which can be administered orally or by intravenous infusion. Formerly, it was used in DIURETICS and EXPECTORANTS.. potassium acetate : A potassium salt comprising equal numbers of potassium and acetate ions	2.07	1	0	potassium salt	food acidity regulator
sodium acetate, anhydrous Sodium Acetate: The trihydrate sodium salt of acetic acid, which is used as a source of sodium ions in solutions for dialysis and as a systemic and urinary alkalizer, diuretic, and expectorant.	2.05	1	0	organic sodium salt	NMR chemical shift reference compound
3-mercaptohexanol 3-mercaptohexanol: structure in first source. 3-mercaptohexanol : An alkanethiol that is hexane substituted at positions 1 and 3 by hydroxy and sulfanyl groups respectively.	2.08	1	0	alkanethiol; primary alcohol	flavouring agent; plant metabolite; Saccharomyces cerevisiae metabolite
spathulenol spathulenol: sesquiterpene alcohol isolated from essential oils of Artemisia vulgaris L. & Artemisia dracunculus L.. spathulenol : A tricyclic sesquiterpenoid that is 4-methylidenedecahydro-1H-cyclopropa[e]azulene carrying three methyl substituents at positions 1, 1 and 7 as well as a hydroxy substituent at position 7.	2.21	1	0
6-hydroxyindole 6-hydroxyindole: structure in first source	2.49	2	0
bromochloroacetic acid Keratins: A class of fibrous proteins or scleroproteins that represents the principal constituent of EPIDERMIS; HAIR; NAILS; horny tissues, and the organic matrix of tooth ENAMEL. Two major conformational groups have been characterized, alpha-keratin, whose peptide backbone forms a coiled-coil alpha helical structure consisting of TYPE I KERATIN and a TYPE II KERATIN, and beta-keratin, whose backbone forms a zigzag or pleated sheet structure. alpha-Keratins have been classified into at least 20 subtypes. In addition multiple isoforms of subtypes have been found which may be due to GENE DUPLICATION.. bromochloroacetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is replaced by bromine while a second is replaced by chlorine. A low-melting (27.5-31.5degreeC), hygroscopic crystalline solid, it can be formed during the disinfection (by chlorination) of water that contains bromide ions and organic matter, so can occur in drinking water as a byproduct of the disinfection process.	2.07	1	0	2-bromocarboxylic acid; monocarboxylic acid; organochlorine compound
rhapontin rhapontin: constituent of rhubarb rhizome	2	1	0	rhaponticin	angiogenesis inhibitor; anti-allergic agent; anti-inflammatory agent; antilipemic drug; antineoplastic agent; apoptosis inducer; EC 2.3.1.85 (fatty acid synthase) inhibitor; hypoglycemic agent; neuroprotective agent; plant metabolite
hydroxyphenethylferulate hydroxyphenethylferulate: from the roots of Atropa acuminata (Solanaceae); structure in first source	2.17	1	0	hydroxycinnamic acid
cinnamaldehyde 3-phenylprop-2-enal : A member of the class of cinnamaldehydes that is prop-2-enal in which a hydrogen at position 3 has been replaced by a phenyl group. The configuration of the double bond is not specified; the name "cinnamaldehyde" is widely used to refer to the E (trans) isomer.. (E)-cinnamaldehyde : The E (trans) stereoisomer of cinnamaldehyde, the parent of the class of cinnamaldehydes.	3.78	10	0	3-phenylprop-2-enal; cinnamaldehydes	antifungal agent; EC 4.3.1.24 (phenylalanine ammonia-lyase) inhibitor; flavouring agent; hypoglycemic agent; plant metabolite; sensitiser; vasodilator agent
elaidic acid [no description available]	2.41	2	0	octadec-9-enoic acid	food component
2-hydroxycinnamic acid trans-2-coumaric acid : The trans-isomer of 2-coumaric acid.. 2-coumaric acid : A monohydroxycinnamic acid in which the hydroxy substituent is located at C-2 of the phenyl ring.	3.64	2	0	2-coumaric acid; phenols	antioxidant; metabolite
3-coumaric acid 3-coumaric acid: RN given refers to cpd without isomeric designation in Chemline. trans-3-coumaric acid : A 3-coumaric acid that is phenol substituted with trans-2-propenoic acid at position C-3.. 3-coumaric acid : A monohydroxycinnamic acid in which the hydroxy substituent is located at C-3 of the phenyl ring.	3.64	2	0	3-coumaric acid
trans-4-coumaric acid hydroxycinnamic acid : Any member of the class of cinnamic acids carrying one or more hydroxy substituents.. trans-4-coumaric acid : The trans-isomer of 4-coumaric acid.. 4-coumaric acid : A coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring.	7.99	61	1	4-coumaric acid	food component; mouse metabolite; plant metabolite
geraniol [no description available]	4.08	4	0	3,7-dimethylocta-2,6-dien-1-ol; monoterpenoid; primary alcohol	allergen; fragrance; plant metabolite; volatile oil component
glycosides [no description available]	6.55	59	0
3-Methoxycinnamic acid [no description available]	2.13	1	0	hydroxycinnamic acid
benzylideneacetone benzylideneacetone: RN given refers to cpd without isomeric; structure in Merck Index, 9th ed, #1153. trans-benzylideneacetone : The trans-isomer of benzylideneacetone. It acts as an inhibitor of the enzyme phospholipase A2 (EC 3.1.1.4) of insects like diamond back moth.. benzylideneacetone : An enone in which a phenyl ring is attached to the beta-carbon atom of but-3-en-2-one. Although both cis- and trans-isomers are possible for the alpha,beta-unsaturated ketone, only the trans-isomer is observed.	2.1	1	0	benzylideneacetone	bacterial metabolite; EC 3.1.1.4 (phospholipase A2) inhibitor; flavouring agent; fragrance
chalcone trans-chalcone : The trans-isomer of chalcone.	4.65	8	0	chalcone	EC 3.2.1.1 (alpha-amylase) inhibitor
sinapinic acid sinapinic acid: a matrix for matrix-assisted laser desorption technique for protein MW determination; a constituent of propolis. trans-sinapic acid : A sinapic acid in which the double bond has trans-configuration.	7.07	24	0	sinapic acid	MALDI matrix material; plant metabolite
isomethyleugenol Methylation: Addition of methyl groups. In histo-chemistry methylation is used to esterify carboxyl groups and remove sulfate groups by treating tissue sections with hot methanol in the presence of hydrochloric acid. (From Stedman, 25th ed)	5.57	17	1	isomethyleugenol
beta-ionone beta-ionone: stimulator of carotenogenesis; carotenoid inhibitor; intermediate in synthesis of Vit A; RN given refers to cpd without isomeric designation; structure. beta-ionone : An ionone that is but-3-en-2-one substituted by a 2,6,6-trimethylcyclohex-1-en-1-yl group at position 4.	2.05	1	0	ionone	antioxidant; fragrance
retinaldehyde Retinaldehyde: A diterpene derived from the carotenoid VITAMIN A which functions as the active component of the visual cycle. It is the prosthetic group of RHODOPSIN (i.e., covalently bonded to ROD OPSIN as 11-cis-retinal). When stimulated by visible light, rhodopsin transforms this cis-isomer of retinal to the trans-isomer (11-trans-retinal). This transformation straightens-out the bend of the retinal molecule and causes a change in the shape of rhodopsin triggering the visual process. A series of energy-requiring enzyme-catalyzed reactions convert the 11-trans-retinal back to the cis-isomer.. all-trans-retinal : A retinal in which all four exocyclic double bonds have E- (trans-) geometry.	1.98	1	0	retinal; vitamin A	gap junctional intercellular communication inhibitor; human metabolite; mouse metabolite
piperine piperine : A N-acylpiperidine that is piperidine substituted by a (1E,3E)-1-(1,3-benzodioxol-5-yl)-5-oxopenta-1,3-dien-5-yl group at the nitrogen atom. It is an alkaloid isolated from the plant Piper nigrum.	3.75	9	0	benzodioxoles; N-acylpiperidine; piperidine alkaloid; tertiary carboxamide	food component; human blood serum metabolite; NF-kappaB inhibitor; plant metabolite
squalene Addavax: an oil-water nanoemulsion and adjuvant containing squalene, Tween 80, and sorbitane trioleate	2.41	2	0	triterpene	human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	6.19	40	0	stilbene
2'-hydroxychalcone 2'-hydroxychalcone : A member of the class of chalcones that is trans-chalcone substituted by a hydroxy group at position 2'.	2.1	1	0	chalcones; phenols	anti-inflammatory agent
isoliquiritigenin [no description available]	3.91	3	0	chalcones	antineoplastic agent; biological pigment; EC 1.14.18.1 (tyrosinase) inhibitor; GABA modulator; geroprotector; metabolite; NMDA receptor antagonist
phenyl-n-tert-butylnitrone phenyl-N-tert-butylnitrone: a spin-trapping agent	2.46	2	0
trichodermamide b trichodermamide B: from cultures of the marine-derived fungus Trichoderma virens; structure in first source	2.17	1	0
2,4,4'-trihydroxydeoxybenzoin 2,4,4'-trihydroxydeoxybenzoin: structure in first source	2.07	1	0
4'-methoxychalcone 4'-methoxychalcone: RN given refers to compound with no isomeric designation	2.08	1	0	chalcones
sorbic acid Sorbic Acid: Mold and yeast inhibitor. Used as a fungistatic agent for foods, especially cheeses.. (2E,4E)-hexa-2,4-dienoic acid : A sorbic acid having trans-double bonds at positions 2 and 4; a food preservative that can induce cutaneous vasodilation and stinging upon topical application to humans. It is the most thermodynamically stable of the four possible geometric isomers possible, as well as the one with the highest antimicrobial activity.. sorbic acid : A hexadienoic acid with double bonds at C-2 and C-4; it has four geometrical isomers, of which the trans,trans-form is naturally occurring.	2.44	2	0	alpha,beta-unsaturated monocarboxylic acid; sorbic acid
ricinoleic acid ricinoleic acid: RN given refers to (R-(Z))-isomer; structure in Merck Index, 9th ed, #8005. ricinoleic acid : A (9Z)-12-hydroxyoctadec-9-enoic acid in which the 12-hydroxy group has R-configuration..	1.96	1	0	(9Z)-12-hydroxyoctadec-9-enoic acid
cannabidiol Cannabidiol: Compound isolated from Cannabis sativa extract.. cannabidiol : An cannabinoid that is cyclohexene which is substituted by a methyl group at position 1, a 2,6-dihydroxy-4-pentylphenyl group at position 3, and a prop-1-en-2-yl group at position 4.	2.31	1	0	olefinic compound; phytocannabinoid; resorcinols	antimicrobial agent; plant metabolite
arginine vasopressin Arginine Vasopressin: The predominant form of mammalian antidiuretic hormone. It is a nonapeptide containing an ARGININE at residue 8 and two disulfide-linked cysteines at residues of 1 and 6. Arg-vasopressin is used to treat DIABETES INSIPIDUS or to improve vasomotor tone and BLOOD PRESSURE.. argipressin : The predominant form of mammalian vasopressin (antidiuretic hormone). It is a nonapeptide containing an arginine at residue 8 and two disulfide-linked cysteines at residues of 1 and 6.	3.93	13	0	vasopressin	cardiovascular drug; hematologic agent; mitogen
azidopine azidopine: structure given in first source	1.98	1	0	benzamides
amygdalin [no description available]	2.77	3	0
tropisetron Tropisetron: An indole derivative and 5-HT3 RECEPTOR antagonist that is used for the prevention of nausea and vomiting.. tropisetron : An indolyl carboxylate ester obtained by formal condensation of the carboxy group of indole-3-carboxylic acid with the hydroxy group of tropine.	1.98	1	0	indolyl carboxylic acid
propylthiouracil Propylthiouracil: A thiourea antithyroid agent. Propythiouracil inhibits the synthesis of thyroxine and inhibits the peripheral conversion of throxine to tri-iodothyronine. It is used in the treatment of hyperthyroidism. (From Martindale, The Extra Pharmacopeoia, 30th ed, p534). 6-propyl-2-thiouracil : A pyrimidinethione consisting of uracil in which the 2-oxo group is substituted by a thio group and the hydrogen at position 6 is substituted by a propyl group.	2.31	1	0	pyrimidinethione	antidote to paracetamol poisoning; antimetabolite; antioxidant; antithyroid drug; carcinogenic agent; EC 1.14.13.39 (nitric oxide synthase) inhibitor; hormone antagonist
nsc 4347 NSC 4347: structure in first source	2.57	2	0
sesquiterpenes [no description available]	3.48	7	0
dienestrol Dienestrol: A synthetic, non-steroidal estrogen structurally related to stilbestrol. It is used, usually as the cream, in the treatment of menopausal and postmenopausal symptoms.. dienestrol : An olefinic compound that is hexa-2,4-diene substituted by 4-hydroxyphenyl groups at positions 3 and 4 respectively.	3.1	1	0
doxepin hydrochloride [no description available]	2.1	1	0
mercaptopurine Mercaptopurine: An antimetabolite antineoplastic agent with immunosuppressant properties. It interferes with nucleic acid synthesis by inhibiting purine metabolism and is used, usually in combination with other drugs, in the treatment of or in remission maintenance programs for leukemia.. purine-6-thiol : A thiol that is the tautomer of mercaptopurine.. mercaptopurine : A member of the class of purines that is 6,7-dihydro-1H-purine carrying a thione group at position 6. An adenine analogue, it is used in the treatment of acute lymphocytic leukemia (ALL), chronic myeloid leukemia (CML), Crohn's disease, and ulcerative colitis.	2.67	3	0	aryl thiol; purines; thiocarbonyl compound	anticoronaviral agent; antimetabolite; antineoplastic agent
3,3',4,5'-tetrahydroxystilbene 3,3',4,5'-tetrahydroxystilbene: demethyl derivative of isorhapontigenin; structure in first source; a Syk kinase inhibitor; found in heartwood of FABACEAE; inhibitor of photosynthesis in spinach chloroplasts; may be inhibitor of plant growth; RN given refers to (E)-isomer. piceatannol : A stilbenol that is trans-stilbene in which one of the phenyl groups is substituted by hydroxy groups at positions 3 and 4, while the other phenyl group is substituted by hydroxy groups at positions 3 and 5.	2.71	3	0	catechols; polyphenol; resorcinols; stilbenol	antineoplastic agent; apoptosis inducer; geroprotector; hypoglycemic agent; plant metabolite; protein kinase inhibitor; tyrosine kinase inhibitor
ethyl coumarate ethyl coumarate: structure in first source	2.21	1	0	cinnamate ester
(2S)-7-hydroxyflavanone [no description available]	3.31	1	0	7-hydroxyflavanone
caffeic acid trans-caffeic acid : The trans-isomer of caffeic acid.	10.71	141	1	caffeic acid	geroprotector; mouse metabolite
methyl caffeate methyl caffeate: from plant Gaillardia pulchella. methyl caffeate : An alkyl caffeate ester formed by the formal condensation of caffeic acid with methyl alcohol.	2.11	1	0	alkyl caffeate ester; methyl ester
captax captax: RN given refers to parent cpd. 1,3-benzothiazole-2-thiol : 1,3-Benzothiazole substituted at the 2-position with a sulfanyl group.	3.1	1	0	aryl thiol; benzothiazoles	carcinogenic agent; metabolite
3-(3,4-dimethoxyphenyl)propenoic acid 3-(3,4-dimethoxyphenyl)propenoic acid: structure given in first source; RN given refers to parent cpd. 3,4-dimethoxycinnamic acid : A methoxycinnamic acid that is trans-cinnamic acid substituted by methoxy groups at positions 3' and 4' respectively.	2.01	1	0	methoxycinnamic acid
3,4,5-trimethoxycinnamic acid 3,4,5-trimethoxycinnamic acid : A methoxycinnamic acid with three methoxy substituents at the 3-, 4- and 5-positions.	1.96	1	0
isoferulic acid isoferulic acid: isomer of ferulic acid; structure. isoferulic acid : A ferulic acid consisting of trans-cinnamic acid bearing methoxy and hydroxy substituents at positions 4 and 3 respectively on the phenyl ring.	2.75	3	0	ferulic acids	antioxidant; biomarker; metabolite
isoeugenol trans-isoeugenol : The trans-stereoisomer of isoeugenol.	2.03	1	0	isoeugenol	plant metabolite
cotinine Cotinine: The N-glucuronide conjugate of cotinine is a major urinary metabolite of NICOTINE. It thus serves as a biomarker of exposure to tobacco SMOKING. It has CNS stimulating properties.. (-)-cotinine : An N-alkylpyrrolidine that consists of N-methylpyrrolidinone bearing a pyridin-3-yl substituent at position C-5 (the 5S-enantiomer). It is an alkaloid commonly found in Nicotiana tabacum.	3.39	1	1	N-alkylpyrrolidine; pyridines; pyrrolidin-2-ones; pyrrolidine alkaloid	antidepressant; biomarker; human xenobiotic metabolite; plant metabolite
flunarizine Flunarizine: Flunarizine is a selective calcium entry blocker with calmodulin binding properties and histamine H1 blocking activity. It is effective in the prophylaxis of migraine, occlusive peripheral vascular disease, vertigo of central and peripheral origin, and as an adjuvant in the therapy of epilepsy.	1.96	1	0	diarylmethane
thiothixene [no description available]	3.1	1	0	N-methylpiperazine	anticoronaviral agent
curcumin Curcumin: A yellow-orange dye obtained from tumeric, the powdered root of CURCUMA longa. It is used in the preparation of curcuma paper and the detection of boron. Curcumin appears to possess a spectrum of pharmacological properties, due primarily to its inhibitory effects on metabolic enzymes.. curcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa.	8.09	27	1	aromatic ether; beta-diketone; diarylheptanoid; enone; polyphenol	anti-inflammatory agent; antifungal agent; antineoplastic agent; biological pigment; contraceptive drug; dye; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; EC 1.8.1.9 (thioredoxin reductase) inhibitor; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; flavouring agent; food colouring; geroprotector; hepatoprotective agent; immunomodulator; iron chelator; ligand; lipoxygenase inhibitor; metabolite; neuroprotective agent; nutraceutical; radical scavenger
hc 030031 2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)-N-(4-isopropylphenyl)acetamide: a TRPA1 channel blocker	2.08	1	0
rhodanine 2-mercaptothiazolinone: metabolite in urine from persons exposed to CS2; structure	7.7	3	0	thiazolidinone
cinnarizine Cinnarizine: A piperazine derivative having histamine H1-receptor and calcium-channel blocking activity with vasodilating and antiemetic properties but it induces PARKINSONIAN DISORDERS.	1.96	1	0	diarylmethane; N-alkylpiperazine; olefinic compound	anti-allergic agent; antiemetic; calcium channel blocker; geroprotector; H1-receptor antagonist; histamine antagonist; muscarinic antagonist
sulindac Sulindac: A sulfinylindene derivative prodrug whose sulfinyl moiety is converted in vivo to an active NSAID analgesic. Specifically, the prodrug is converted by liver enzymes to a sulfide which is excreted in the bile and then reabsorbed from the intestine. This helps to maintain constant blood levels with reduced gastrointestinal side effects.. sulindac : A monocarboxylic acid that is 1-benzylidene-1H-indene which is substituted at positions 2, 3, and 5 by methyl, carboxymethyl, and fluorine respectively, and in which the phenyl group of the benzylidene moiety is substituted at the para position by a methylsulfinyl group. It is a prodrug for the corresponding sulfide, a non-steroidal anti-inflammatory drug, used particularly in the treatment of acute and chronic inflammatory conditions.	2.03	1	0	monocarboxylic acid; organofluorine compound; sulfoxide	analgesic; antineoplastic agent; antipyretic; apoptosis inducer; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; prodrug; tocolytic agent
capsaicin ALGRX-4975: an injectable capsaicin (TRPV1 receptor agonist) formulation for longlasting pain relief. capsaicinoid : A family of aromatic fatty amides produced as secondary metabolites by chilli peppers.	3.81	3	0	capsaicinoid	non-narcotic analgesic; TRPV1 agonist; voltage-gated sodium channel blocker
metiamide Metiamide: A histamine H2 receptor antagonist that is used as an anti-ulcer agent.	1.95	1	0	imidazoles
terbinafine [no description available]	2.47	2	0	acetylenic compound; allylamine antifungal drug; enyne; naphthalenes; tertiary amine	EC 1.14.13.132 (squalene monooxygenase) inhibitor; P450 inhibitor; sterol biosynthesis inhibitor
coniferyl alcohol coniferyl alcohol: structure. coniferol : A phenylpropanoid that is one of the main monolignols, produced by the reduction of the carboxy functional group in cinnamic acid and the addition of a hydroxy and a methoxy substituent to the aromatic ring.	2.07	1	0	guaiacols; phenylpropanoid	animal metabolite; monolignol; mouse metabolite; pheromone; plant metabolite; volatile oil component
n-(4-(n-(3-methoxypyrazin-2-yl)sulfamoyl)phenyl)-3-(5-nitrothiophene-2-yl)acrylamide N-(4-(N-(3-methoxypyrazin-2-yl)sulfamoyl)phenyl)-3-(5-nitrothiophene-2-yl)acrylamide: prevents the necrosome from interacting with downstream effectors; structure in first source. necrosulfonamide : A sulfonamide that is a 3-methoxypyrazin-2-yl derivative of (E)-N-(4-(N-(4,6-dimethylpyrimidin-2-yl)sulfamoyl)phenyl)-3-(5-nitrothiophene-2-yl)acrylamide. Necrosulfonamide specifically blocks necrosis downstream of the activation of RIP3 (the receptor-interacting serine-threonine kinase 3), a key signalling molecule in the programmed necrosis (necroptosis) pathway.	2.21	1	0	pyrazines; sulfonamide; thiophenes	necroptosis inhibitor; neuroprotective agent
oxazolone Oxazolone: Immunologic adjuvant and sensitizing agent.	2.13	1	0
caryophyllene oxide caryophyllene oxide: has butyrylcholinesterase inhibitory activity; structure in first source. epoxide : Any cyclic ether in which the oxygen atom forms part of a 3-membered ring.	2.13	1	0	epoxide	metabolite
chlorogenic acid caffeoylquinic acid: Antiviral Agent; structure in first source. chlorogenate : A monocarboxylic acid anion that is the conjugate base of chlorogenic acid; major species at pH 7.3.	10.1	95	2	cinnamate ester; tannin	food component; plant metabolite
thiobarbituric acid thiobarbituric acid: RN given refers to parent cpd. 2-thiobarbituric acid : A barbiturate, the structure of which is that of barbituric acid in which the oxygen at C-2 is replaced by sulfur.	1.98	1	0	barbiturates	allergen; reagent
thiourea Thiourea: A photographic fixative used also in the manufacture of resins. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), this substance may reasonably be anticipated to be a carcinogen (Merck Index, 9th ed). Many of its derivatives are ANTITHYROID AGENTS and/or FREE RADICAL SCAVENGERS.. thiourea : The simplest member of the thiourea class, consisting of urea with the oxygen atom substituted by sulfur.	2.38	2	0	one-carbon compound; thioureas; ureas	antioxidant; chromophore
D-fructopyranose [no description available]	3.65	8	0	cyclic hemiketal; D-fructose; fructopyranose	sweetening agent
thioacetamide Thioacetamide: A crystalline compound used as a laboratory reagent in place of HYDROGEN SULFIDE. It is a potent hepatocarcinogen.. thioacetamide : A thiocarboxamide consiting of acetamide having the oxygen replaced by sulfur.	3.07	3	0	thiocarboxamide	hepatotoxic agent
brij-58 Cetomacrogol: Non-ionic surfactant of the polyethylene glycol family. It is used as a solubilizer and emulsifying agent in foods, cosmetics, and pharmaceuticals, often as an ointment base, and also as a research tool.	2.57	2	0
tungsten carbide tungsten carbide: RN given refers to cpd with unspecified MF	2.15	1	0
digoxin Digoxin: A cardiotonic glycoside obtained mainly from Digitalis lanata; it consists of three sugars and the aglycone DIGOXIGENIN. Digoxin has positive inotropic and negative chronotropic activity. It is used to control ventricular rate in ATRIAL FIBRILLATION and in the management of congestive heart failure with atrial fibrillation. Its use in congestive heart failure and sinus rhythm is less certain. The margin between toxic and therapeutic doses is small. (From Martindale, The Extra Pharmacopoeia, 30th ed, p666). digoxin : A cardenolide glycoside that is digitoxin beta-hydroxylated at C-12. A cardiac glycoside extracted from the foxglove plant, Digitalis lanata, it is used to control ventricular rate in atrial fibrillation and in the management of congestive heart failure with atrial fibrillation, but the margin between toxic and therapeutic doses is small.	2.44	2	0	cardenolide glycoside; steroid saponin	anti-arrhythmia drug; cardiotonic drug; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; epitope
1,6-anhydro-beta-glucopyranose 1,6-anhydro-beta-glucopyranose: RN given refers to (beta-D)-isomer. levoglucosan : A anhydrohexose that is the 1,6-anhydro-derivative of beta-D-glucopyranose.	2.02	1	0	anhydrohexose	Arabidopsis thaliana metabolite; biomarker; human metabolite
buthionine buthionine: RN given refers to cpd without isomeric designation	7.06	1	0
ytterbium(iii) triflate [no description available]	2.08	1	0
1,3-dihydroxy-4,4,5,5-tetramethyl-2-(4-carboxyphenyl)tetrahydroimidazole 1,3-dihydroxy-4,4,5,5-tetramethyl-2-(4-carboxyphenyl)tetrahydroimidazole: intermediate in the synthesis of imidazolineoxyl N-oxides; partial structure given in first source	2.01	1	0	benzoic acid; imidazolines; organic radical	apoptosis inhibitor; radical scavenger
tamoxifen [no description available]	2.52	2	0	stilbenoid; tertiary amino compound	angiogenesis inhibitor; antineoplastic agent; bone density conservation agent; EC 1.2.3.1 (aldehyde oxidase) inhibitor; EC 2.7.11.13 (protein kinase C) inhibitor; estrogen antagonist; estrogen receptor antagonist; estrogen receptor modulator
sodium taurodeoxycholate Taurodeoxycholic Acid: A bile salt formed in the liver by conjugation of deoxycholate with taurine, usually as the sodium salt. It is used as a cholagogue and choleretic, also industrially as a fat emulsifier.. taurodeoxycholic acid : A bile acid taurine conjugate of deoxycholic acid.. taurodeoxycholate : An organosulfonate oxoanion that is the conjugate base of taurodeoxycholic acid.	1.97	1	0	bile acid taurine conjugate	human metabolite
4-methylumbelliferyl glucoside 4-methylumbelliferyl glucoside: RN given refers to (beta)-isomer. 4-methylumbelliferyl beta-D-glucoside : A beta-D-glucoside having a 4-methylumbelliferyl substituent at the anomeric position.	2.1	1	0	beta-D-glucoside; coumarins; monosaccharide derivative	chromogenic compound
nadp [no description available]	3.86	12	0
1,1-diphenyl-2-picrylhydrazyl 1,1-diphenyl-2-picrylhydrazyl: A diphenyl picrate; the ability to decolorize this stable radical indicates reactivity of tested compounds (Banda, Anal Chem 46:1772-7 1974)	10.01	115	1
fusidic acid Fusidic Acid: An antibiotic isolated from the fermentation broth of Fusidium coccineum. (From Merck Index, 11th ed). It acts by inhibiting translocation during protein synthesis.. fusidic acid : A steroid antibiotic that is isolated from the fermentation broth of Fusidium coccineum.	2.05	1	0	11alpha-hydroxy steroid; 3alpha-hydroxy steroid; alpha,beta-unsaturated monocarboxylic acid; steroid acid; steroid antibiotic; sterol ester	EC 2.7.1.33 (pantothenate kinase) inhibitor; Escherichia coli metabolite; protein synthesis inhibitor
Geraniin [no description available]	2.47	2	0	tannin
helvolic acid helvolic acid: structure. helvolic acid : A steroid C-21 acid having a 29-nordammarane skeleton substituted with an acetoxy group at C-16 and oxo groups at C-3 and -7, with double bonds at C-1, -17(20) and -24.	2.17	1	0	3-oxo-Delta(1) steroid; acetate ester; monocarboxylic acid; steroid acid	antibacterial agent; fungal metabolite; mycotoxin
u 0126 U 0126: protein kinase kinase inhibitor; structure in first source	2.45	2	0	aryl sulfide; dinitrile; enamine; substituted aniline	antineoplastic agent; antioxidant; apoptosis inducer; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; osteogenesis regulator; vasoconstrictor agent
telaprevir [no description available]	2.11	1	0	cyclopentapyrrole; cyclopropanes; oligopeptide; pyrazines	antiviral drug; hepatitis C protease inhibitor; peptidomimetic
laccase Laccase: A copper-containing oxidoreductase enzyme that catalyzes the oxidation of 4-benzenediol to 4-benzosemiquinone. It also has activity towards a variety of O-quinols and P-quinols. It primarily found in FUNGI and is involved in LIGNIN degradation, pigment biosynthesis and detoxification of lignin-derived products.	5.08	39	0
lithium Lithium: An element in the alkali metals family. It has the atomic symbol Li, atomic number 3, and atomic weight [6.938; 6.997]. Salts of lithium are used in treating BIPOLAR DISORDER.	7.91	4	0	alkali metal atom
cobaltous chloride cobaltous chloride: RN given refers to unlabeled cpd; RN in Chemline for cobalt trichloride: 10241-04-0; RN for 60-labeled cpd: 14543-09-0; RN for 57-labeled cpd: 164113-89-1; RN for 58-labeled cpd: 29377-09-1; structure. cobalt dichloride : A cobalt salt in which the cobalt metal is in the +2 oxidation state and the counter-anion is chloride. It is used as an indicator for water in desiccants.	3.16	5	0	cobalt salt; inorganic chloride	allergen; calcium channel blocker; sensitiser; two-colour indicator
raclopride Raclopride: A substituted benzamide that has antipsychotic properties. It is a dopamine D2 receptor (see RECEPTORS, DOPAMINE D2) antagonist.	1.98	1	0	salicylamides
orlistat Orlistat: A lactone derivative of LEUCINE that acts as a pancreatic lipase inhibitor to limit the absorption of dietary fat; it is used in the management of obesity.. orlistat : A carboxylic ester resulting from the formal condensation of the carboxy group of N-formyl-L-leucine with the hydroxy group of (3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one. A pancreatic lipase inhibitor, it is used as an anti-obesity drug.	2.07	1	0	beta-lactone; carboxylic ester; formamides; L-leucine derivative	anti-obesity agent; bacterial metabolite; EC 2.3.1.85 (fatty acid synthase) inhibitor; EC 3.1.1.3 (triacylglycerol lipase) inhibitor
quinine [no description available]	4.35	4	1	cinchona alkaloid	antimalarial; muscle relaxant; non-narcotic analgesic
mitragynine [no description available]	2.17	1	0	monoterpenoid indole alkaloid
1,2-bis(2-aminophenoxy)ethane n,n,n',n'-tetraacetic acid acetoxymethyl ester [no description available]	3.11	5	0
u-50488 3,4-Dichloro-N-methyl-N-(2-(1-pyrrolidinyl)-cyclohexyl)-benzeneacetamide, (trans)-Isomer: A non-peptide, kappa-opioid receptor agonist which has also been found to stimulate the release of adrenocorticotropin (ADRENOCORTICOTROPIC HORMONE) via the release of hypothalamic arginine vasopressin (ARGININE VASOPRESSIN) and CORTICOTROPIN-RELEASING HORMONE. (From J Pharmacol Exp Ther 1997;280(1):416-21). U50488 : A monocarboxylic acid amide obtained by formal condensation between the carboxy group of 3,4-dichlorophenylacetic acid and the secondary amino group of (1R,2R)-N-methyl-2-(pyrrolidin-1-yl)cyclohexanamine	1.97	1	0	dichlorobenzene; monocarboxylic acid amide; N-alkylpyrrolidine	analgesic; antitussive; calcium channel blocker; diuretic; kappa-opioid receptor agonist
sch 23390 SCH 23390: a selective D1-receptor antagonist. SCH 23390 : A benzazepine that is 2,3,4,5-tetrahydro-3-benzazepine bearing a phenyl substituent at position 1, a methyl substituent at position 3, a chloro substituent at position 7 and a hydroxy substituent at position 8.	3.1	1	0	benzazepine
paynantheine paynantheine: structure in first source	2.17	1	0
thionicotinamide adenine dinucleotide phosphate [no description available]	1.99	1	0
1,2-diamino-4,5-methylenedioxybenzene 1,2-diamino-4,5-methylenedioxybenzene: used to determine alpha-keto acids in human serum & urine	2.31	1	0
calixarenes Calixarenes: Phenolic metacyclophanes derived from condensation of PHENOLS and ALDEHYDES. The name derives from the vase-like molecular structures. A bracketed [n] indicates the number of aromatic rings.. calixarenes : Originally macrocyclic compounds capable of assuming a basket (or "calix") shaped conformation. They are formed from p-hydrocarbyl phenols and formaldehyde. The term now applies to a variety of derivatives by substitution of the hydrocarbon cyclo{oligo[(1,3-phenylene)methylene]}.. calixarene : A macrocycle composed of 1,3-phenylene groups linked by methylene groups. The number of 1,3-phenylene units in the macrocycle is denoted by the "n" in calix[n]arene name.	2	1	0
chimonanthine chimonanthine: structure in first source. chimonanthine : A ring assembly that is 2,2',3,3',8,8',8a,8a'-octahydro-1H,1'H-3a,3a'-bipyrrolo[2,3-b]indole substituted by methyl groups at positions 1 and 1'.	2.17	1	0	chimonanthine
cytellin cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982	4.79	30	0
gigantol gigantol: structure in first source	2.5	2	0
ginsenosides ginsenoside : Triterpenoid saponins with a dammarane-like skeleton originally isolated from ginseng (Panax) species. Use of the term has been extended to include semi-synthetic derivatives.	2.03	1	0
silybin [no description available]	2.1	1	0
ovalbumin Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.	8.26	6	0
sodium dodecyl sulfate Sodium Dodecyl Sulfate: An anionic surfactant, usually a mixture of sodium alkyl sulfates, mainly the lauryl; lowers surface tension of aqueous solutions; used as fat emulsifier, wetting agent, detergent in cosmetics, pharmaceuticals and toothpastes; also as research tool in protein biochemistry.. sodium dodecyl sulfate : An organic sodium salt that is the sodium salt of dodecyl hydrogen sulfate.	3.34	6	0	organic sodium salt	detergent; protein denaturant
butin butin: isolated from seeds of Butea monosperma; structure given in first source. butin : A trihydroxyflavanone in which the three hydroxy substituents are located at positions 3', 4' and 7. It is found in Acacia mearnsii, Vernonia anthelmintica and Dalbergia odorifera and has a protective affect against oxidative stress-induced mitochondrial dysfunction.	2.17	1	0	flavanones
crocin crocin: a free radical scavenger	2.03	1	0
galactomannan galactomannan: a galectin inhibitor. galactomannan : A heteroglycan consisting of a mannan backbone with galactose side groups.	2.25	1	0	oligosaccharide
2-amino-4-nitrophenol [no description available]	2.02	1	0	4-nitrophenols
flavan-3-ol flavan-3-ol: structure in first source	3.57	8	0	hydroxyflavonoid
fg 9041 FG 9041: structure given in first source	2	1	0	quinoxaline derivative
homoserine lactone homoserine lactone: a putative signal for starvation in E. coli; structure in first source. homoserinium lactone : The conjugate acid of homoserine lactone; major species at pH 7.3.. homoserine lactone : A butan-4-olide having an amino substituent at the 2-position.	2.13	1	0	ammonium ion derivative; organic cation
naphthoquinones Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.	3.54	8	0
digitoxigenin Digitoxigenin: 3 beta,14-Dihydroxy-5 beta-card-20(22)enolide. A cardenolide which is the aglycon of digitoxin. Synonyms: Cerberigenin; Echujetin; Evonogenin; Thevetigenin.. digitoxigenin : A 5beta-cardenolide that is 5beta-cardanolide with hydroxy substituents at the 3beta- and 14beta-positions and double bond unsaturation at C(20)-C(22).	3.1	1	0	14beta-hydroxy steroid; 3beta-hydroxy steroid
sitagliptin sitagliptin : A triazolopyrazine that exhibits hypoglycemic activity.	3.27	1	0	triazolopyrazine; trifluorobenzene	EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; environmental contaminant; hypoglycemic agent; serine proteinase inhibitor; xenobiotic
tolcapone Tolcapone: A benzophenone and nitrophenol compound that acts as an inhibitor of CATECHOL O-METHYLTRANSFERASE, an enzyme involved in the metabolism of DOPAMINE and LEVODOPA. It is used in the treatment of PARKINSON DISEASE in patients for whom levodopa is ineffective or contraindicated.. tolcapone : Benzophenone substituted on one of the phenyl rings at C-3 and C-4 by hydroxy groups and at C-5 by a nitro group, and on the other phenyl ring by a methyl group at C-4. It is an inhibitor of catechol O-methyltransferase.	2.21	1	0	2-nitrophenols; benzophenones; catechols	antiparkinson drug; EC 2.1.1.6 (catechol O-methyltransferase) inhibitor
3-deoxyisoochracinic acid 3-deoxyisoochracinic acid: structure in first source	2.17	1	0
pyrroloquinoline pyrroloquinoline: check to see if actually PYRROLOQUINOLINE QUINONE (PQQ COFACTOR)	2.25	1	0
2-mercaptoacetate 2-mercaptoacetate: RN given refers to parent cpd	2.1	1	0	monocarboxylic acid anion
catechin gallate catechin gallate: structure in first source. (+)-catechin-3-O-gallate : A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3S)-hydroxy group of (+)-catechin.	3.02	4	0	flavans; gallate ester; polyphenol	metabolite
gallocatechin-3-gallate gallocatechin gallate: structure in first source. (+)-gallocatechin gallate : A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3S)-hydroxy group of (+)-gallocatechin.	3.08	4	0	catechin; gallate ester; polyphenol	plant metabolite
sphingosine sphing-4-enine : A sphingenine in which the C=C double bond is located at the 4-position.. sphingenine : A 2-aminooctadecene-1,3-diol having (2S,3R)-configuration.. sphingoid : Sphinganine, its homologs and stereoisomers, and the hydroxy and unsaturated derivatives of these compounds.. 2-aminooctadec-4-ene-1,3-diol : A 2-aminooctadecene-1,3-diol having its double bond at position 4.	2.7	3	0	sphing-4-enine	human metabolite; mouse metabolite
quercetin [no description available]	11.17	234	1	7-hydroxyflavonol; pentahydroxyflavone	antibacterial agent; antineoplastic agent; antioxidant; Aurora kinase inhibitor; chelator; EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor; geroprotector; phytoestrogen; plant metabolite; protein kinase inhibitor; radical scavenger
bilirubin [no description available]	4.35	6	0	biladienes; dicarboxylic acid	antioxidant; human metabolite; mouse metabolite
dinoprostone prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.	5.04	41	0	prostaglandins E	human metabolite; mouse metabolite; oxytocic
dinoprost Dinoprost: A naturally occurring prostaglandin that has oxytocic, luteolytic, and abortifacient activities. Due to its vasocontractile properties, the compound has a variety of other biological actions.. prostaglandin F2alpha : A prostaglandins Falpha that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15. It is a naturally occurring prostaglandin used to induce labor.	5.44	15	1	monocarboxylic acid; prostaglandins Falpha	human metabolite; mouse metabolite
biochanin a [no description available]	2.04	1	0	4'-methoxyisoflavones; 7-hydroxyisoflavones	antineoplastic agent; EC 3.5.1.99 (fatty acid amide hydrolase) inhibitor; phytoestrogen; plant metabolite; tyrosine kinase inhibitor
formononetin [no description available]	3.59	2	0	4'-methoxyisoflavones; 7-hydroxyisoflavones	phytoestrogen; plant metabolite
sinapine sinapine: black mustard seeds, seeds of Brassica nigra; RN given refers to parent; structure. sinapine : An acylcholine in which the acyl group specified is sinapoyl.	2.21	1	0	acylcholine	antioxidant; photosynthetic electron-transport chain inhibitor; plant metabolite
arachidonyltrifluoromethane arachidonyltrifluoromethane: structure given in first source; inhibits 85-kDa phospholipase A2. AACOCF3 : A fatty acid derivative that is arachidonic acid in which the OH part of the carboxy group has been replaced by a trifluoromethyl group	2.01	1	0	fatty acid derivative; ketone; olefinic compound; organofluorine compound	EC 3.1.1.4 (phospholipase A2) inhibitor
tylosin [no description available]	2.1	1	0	aldehyde; disaccharide derivative; enone; leucomycin; macrolide antibiotic; monosaccharide derivative	allergen; bacterial metabolite; environmental contaminant; xenobiotic
acacetin 5,7-dihydroxy-4'-methoxyflavone : A monomethoxyflavone that is the 4'-methyl ether derivative of apigenin.	2.15	1	0	dihydroxyflavone; monomethoxyflavone	anticonvulsant; plant metabolite
apigenin Chamomile: Common name for several daisy-like plants (MATRICARIA; TRIPLEUROSPERMUM; ANTHEMIS; CHAMAEMELUM) native to Europe and Western Asia, now naturalized in the United States and Australia.	6.38	20	0	trihydroxyflavone	antineoplastic agent; metabolite
luteolin [no description available]	7.74	28	1	3'-hydroxyflavonoid; tetrahydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; apoptosis inducer; c-Jun N-terminal kinase inhibitor; EC 2.3.1.85 (fatty acid synthase) inhibitor; immunomodulator; nephroprotective agent; plant metabolite; radical scavenger; vascular endothelial growth factor receptor antagonist
7,3'-dihydroxy-4'-methoxyisoflavone 7,3'-dihydroxy-4'-methoxyisoflavone: isolated from Astragali radix; structure in first source. calycosin : A member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone which is substituted by an additional hydroxy group at the 3' position and a methoxy group at the 4' position.	2.55	2	0	4'-methoxyisoflavones; 7-hydroxyisoflavones	antioxidant; metabolite
linoleic acid Linoleic Acid: A doubly unsaturated fatty acid, occurring widely in plant glycosides. It is an essential fatty acid in mammalian nutrition and is used in the biosynthesis of prostaglandins and cell membranes. (From Stedman, 26th ed). linoleic acid : An octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry.	5.64	17	0	octadecadienoic acid; omega-6 fatty acid	algal metabolite; Daphnia galeata metabolite; plant metabolite
calcitriol dihydroxy-vitamin D3: as a major in vitro metabolite of 1alpha,25-dihydroxyvitamin D3, produced in primary cultures of neonatal human keratinocytes	2.67	3	0	D3 vitamins; hydroxycalciol; triol	antineoplastic agent; antipsoriatic; bone density conservation agent; calcium channel agonist; calcium channel modulator; hormone; human metabolite; immunomodulator; metabolite; mouse metabolite; nutraceutical
pinosylvin pinosylvin: phytoalexin found in pine and eucalyptus	2.06	1	0	pinosylvin
quercitrin [no description available]	4.2	16	0	alpha-L-rhamnoside; monosaccharide derivative; quercetin O-glycoside; tetrahydroxyflavone	antileishmanial agent; antioxidant; EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.14.18.1 (tyrosinase) inhibitor; plant metabolite
scopoletin [no description available]	4.75	9	0	hydroxycoumarin	plant growth regulator; plant metabolite
vomifoliol blumenol A: a phytotoxin isolated from Oryza sativa Awaakamai; structure in first source. vomifoliol : A fenchane monoterpenoid that is 3,5,5-trimethylcyclohex-2-en-1-one substituted by a hydroxy and a (1E)-3-hydroxybut-1-en-1-yl group at position 4.. (6S,9R)-vomifoliol : A (6S)-vomifoliol with a R configuration for the hydroxy group at position 9.	2.05	1	0	(6S)-vomifoliol	metabolite; phytotoxin
beta carotene beta Carotene: A carotenoid that is a precursor of VITAMIN A. Beta carotene is administered to reduce the severity of photosensitivity reactions in patients with erythropoietic protoporphyria (PORPHYRIA, ERYTHROPOIETIC).. provitamin A : A provitamin that can be converted into vitamin A by enzymes from animal tissues.	5.41	18	0	carotenoid beta-end derivative; cyclic carotene	antioxidant; biological pigment; cofactor; ferroptosis inhibitor; human metabolite; mouse metabolite; plant metabolite; provitamin A
leukotriene b4 Leukotriene B4: The major metabolite in neutrophil polymorphonuclear leukocytes. It stimulates polymorphonuclear cell function (degranulation, formation of oxygen-centered free radicals, arachidonic acid release, and metabolism). (From Dictionary of Prostaglandins and Related Compounds, 1990). leukotriene B4 : A leukotriene composed of (6Z,8E,10E,14Z)-icosatetraenoic acid having (5S)- and (12R)-hydroxy substituents. It is a lipid mediator of inflammation that is generated from arachidonic acid via the 5-lipoxygenase pathway.	3.23	6	0	dihydroxy monocarboxylic acid; hydroxy polyunsaturated fatty acid; leukotriene; long-chain fatty acid	human metabolite; mouse metabolite; plant metabolite; vasoconstrictor agent
leukotriene c4 Leukotriene C4: The conjugation product of LEUKOTRIENE A4 and glutathione. It is the major arachidonic acid metabolite in macrophages and human mast cells as well as in antigen-sensitized lung tissue. It stimulates mucus secretion in the lung, and produces contractions of nonvascular and some VASCULAR SMOOTH MUSCLE. (From Dictionary of Prostaglandins and Related Compounds, 1990). leukotriene C4 : A leukotriene that is (5S,7E,9E,11Z,14Z)-5-hydroxyicosa-7,9,11,14-tetraenoic acid in which a glutathionyl group is attached at position 6 via a sulfide linkage.	2.03	1	0	leukotriene	bronchoconstrictor agent; human metabolite; mouse metabolite
thromboxane a2 Thromboxane A2: An unstable intermediate between the prostaglandin endoperoxides and thromboxane B2. The compound has a bicyclic oxaneoxetane structure. It is a potent inducer of platelet aggregation and causes vasoconstriction. It is the principal component of rabbit aorta contracting substance (RCS).. thromboxane A2 : A thromboxane which is produced by activated platelets and has prothrombotic properties: it stimulates activation of new platelets as well as increases platelet aggregation.	3.07	5	0	epoxy monocarboxylic acid; thromboxanes A	mouse metabolite
sinapyl alcohol sinapyl alcohol: has anti-inflammatory and antinociceptive properties; structure in first source. trans-sinapyl alcohol : Sinapyl alcohol in which the configuration of the propenyl double bond is E. It is one of the main monolignols.. sinapyl alcohol : A primary alcohol, being cinnamyl alcohol hydroxylated at C-4 and methoxylated at C-3 and -5.	2.07	1	0	sinapyl alcohol	monolignol
retinol palmitate retinol palmitate: RN given refers to parent cpd; structure. retinyl palmitate : A palmitate ester of retinol with undefined geometry about the C=C bonds.. all-trans-retinyl palmitate : An all-trans-retinyl ester obtained by formal condensation of the carboxy group of palmitic (hexadecanoic acid) with the hydroxy group of all-trans-retinol. It is used in cosmetic products to treat various skin disorders such as acne, skin aging, wrinkles, dark spots, and also protect against psoriasis.	2.01	1	0	all-trans-retinyl ester; retinyl palmitate	antioxidant; Escherichia coli metabolite; human xenobiotic metabolite
coniferaldehyde coniferaldehyde: from aqueous extract of Senra incana. coniferyl aldehyde : A member of the class of cinnamaldehydes that is cinnamaldehyde substituted by a hydroxy group at position 4 and a methoxy group at position 3.	2.25	1	0	cinnamaldehydes; guaiacols; phenylpropanoid	antifungal agent; plant metabolite
feruloyltyramine feruloyltyramine: structure given in first source; isolated from Cannabis sativa seeds, roots, leaves, and resin; induces hypothermia and motor incoordination in mice; moupinamide is (E)-isomer	2.17	1	0	tyramines	metabolite
hymecromone Hymecromone: A coumarin derivative possessing properties as a spasmolytic, choleretic and light-protective agent. It is also used in ANALYTICAL CHEMISTRY TECHNIQUES for the determination of NITRIC ACID.	3.1	1	0	hydroxycoumarin	antineoplastic agent; hyaluronic acid synthesis inhibitor
daphnetin [no description available]	2.04	1	0	hydroxycoumarin
luteolin-7-glucoside luteolin-7-glucoside: has both antiasthmatic and antineoplastic activities; has 3C protease inhibitory activity; isolated from Ligustrum lucidum. luteolin 7-O-beta-D-glucoside : A glycosyloxyflavone that is luteolin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	2.84	3	0	beta-D-glucoside; glycosyloxyflavone; monosaccharide derivative; trihydroxyflavone	antioxidant; plant metabolite
gossypetin gossypetin: inhibits activity of penicillinase enzyme in E coli. gossypetin : A hexahydroxyflavone having the hydroxy groups placed at the 3-, 3'-, 4'-, 5- 7- and 8-positions.	2.06	1	0	7-hydroxyflavonol; hexahydroxyflavone	plant metabolite
chrysoeriol chrysoeriol: isolated from leaves of Eurya japonica & E. emarginata. 4',5,7-trihydroxy-3'-methoxyflavone : The 3'-O-methyl derivative of luteolin.	2.75	3	0	monomethoxyflavone; trihydroxyflavone	antineoplastic agent; antioxidant; metabolite
quercetin 3-o-methyl ether quercetin 3-O-methyl ether: from Rhamnus species; structure in first source. 3',4',5,7-tetrahydroxy-3-methoxyflavone : A tetrahydroxyflavone having the 4-hydroxy groups located at the 3'- 4'- 5- and 7-positions as well as a methoxy group at the 2-position.	2.11	1	0	monomethoxyflavone; tetrahydroxyflavone	antimicrobial agent; metabolite
apigetrin apigetrin: structure given in first source. apigenin 7-O-beta-D-glucoside : A glycosyloxyflavone that is apigenin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	2.21	1	0	beta-D-glucoside; dihydroxyflavone; glycosyloxyflavone; monosaccharide derivative	antibacterial agent; metabolite; non-steroidal anti-inflammatory drug
alprostadil [no description available]	2.9	4	0	prostaglandins E	anticoagulant; human metabolite; platelet aggregation inhibitor; vasodilator agent
5-hydroxy-6,8,11,14-eicosatetraenoic acid 5(S)-HETE : A HETE having a (5S)-hydroxy group and (6E)-, (8Z)-, (11Z)- and (14Z)-double bonds.. 5-HETE : A HETE having a 5-hydroxy group and (6E)-, (8Z)-, (11Z)- and (14Z)-double bonds.	2.66	3	0	HETE	human metabolite; mouse metabolite
vitamin d 2 Ergocalciferols: Derivatives of ERGOSTEROL formed by ULTRAVIOLET RAYS breaking of the C9-C10 bond. They differ from CHOLECALCIFEROL in having a double bond between C22 and C23 and a methyl group at C24.. vitamin D2 : A vitamin D supplement and has been isolated from alfalfa.	3.1	1	0	hydroxy seco-steroid; seco-ergostane; vitamin D	bone density conservation agent; nutraceutical; plant metabolite; rodenticide
stigmasterol stigmasta-5,22-dien-3-ol: isolated from freeze-dried powder of Blackberries (Rubus ursinus L.) which showed an activity on inhibition of chemocarcinogen. stigmasterol : A 3beta-sterol that consists of 3beta-hydroxystigmastane having double bonds at the 5,6- and 22,23-positions.	4.29	5	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; phytosterols; stigmastane sterol	plant metabolite
cholecalciferol Cholecalciferol: Derivative of 7-dehydroxycholesterol formed by ULTRAVIOLET RAYS breaking of the C9-C10 bond. It differs from ERGOCALCIFEROL in having a single bond between C22 and C23 and lacking a methyl group at C24.. calciol : A hydroxy seco-steroid that is (5Z,7E)-9,10-secocholesta-5,7,10(19)-triene in which the pro-S hydrogen at position 3 has been replaced by a hydroxy group. It is the inactive form of vitamin D3, being hydroxylated in the liver to calcidiol (25-hydroxyvitamin D3), which is then further hydroxylated in the kidney to give calcitriol (1,25-dihydroxyvitamin D3), the active hormone.	3.1	1	0	D3 vitamins; hydroxy seco-steroid; seco-cholestane; secondary alcohol; steroid hormone	geroprotector; human metabolite
sinapaldehyde sinapyl aldehyde: structure in first source. (E)-sinapaldehyde : A member of the class of cinnamaldehydes that is cinnamaldehyde substituted by a hydroxy group at position 4 and methoxy groups at positions 3 and 5.	2.25	1	0	cinnamaldehydes; dimethoxybenzene; phenols	antifungal agent; plant metabolite
quercetin 3-o-glucopyranoside quercetin 3-O-glucopyranoside: structure in first source. quercetin 3-O-beta-D-glucopyranoside : A quercetin O-glucoside that is quercetin with a beta-D-glucosyl residue attached at position 3. Isolated from Lepisorus contortus, it exhibits antineoplastic activityand has been found to decrease the rate of polymerization and sickling of red blood cells	3.57	8	0	beta-D-glucoside; monosaccharide derivative; quercetin O-glucoside; tetrahydroxyflavone	antineoplastic agent; antioxidant; antipruritic drug; bone density conservation agent; geroprotector; histamine antagonist; osteogenesis regulator; plant metabolite
rutin Hydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders.	8.98	88	0	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite
kaempferol [no description available]	11.7	40	0	7-hydroxyflavonol; flavonols; tetrahydroxyflavone	antibacterial agent; geroprotector; human blood serum metabolite; human urinary metabolite; human xenobiotic metabolite; plant metabolite
6-ketoprostaglandin f1 alpha 6-Ketoprostaglandin F1 alpha: The physiologically active and stable hydrolysis product of EPOPROSTENOL. Found in nearly all mammalian tissue.. 6-oxoprostaglandin F1alpha : A prostaglandin Falpha that is prostaglandin F1alpha bearing a keto substituent at the 6-position.	3.84	12	0	prostaglandins Falpha	human metabolite; mouse metabolite
alpha-linolenic acid linolenic acid : A two-membered subclass of octadecatrienoic acid comprising the (9Z,12Z,15Z)- and (6Z,9Z,12Z)-isomers. Linolenic acids are nutrients essential to the formation of prostaglandins and are also used in making paints and synthetic resins.. linolenate : A polyunsaturated fatty acid anion obtained by deprotonation of the carboxy group of either alpha- or gamma-linolenic acid.	2.07	1	0	linolenic acid; omega-3 fatty acid	micronutrient; mouse metabolite; nutraceutical
harmine Harmine: Alkaloid isolated from seeds of PEGANUM HARMALA; ZYGOPHYLLACEAE. It is identical to banisterine, or telepathine, from Banisteria caapi and is one of the active ingredients of hallucinogenic drinks made in the western Amazon region from related plants. It has no therapeutic use, but (as banisterine) was hailed as a cure for postencephalitic PARKINSON DISEASE in the 1920's.. harmine : A harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7.	2.17	1	0	harmala alkaloid	anti-HIV agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; metabolite
genistein [no description available]	6.16	16	0	7-hydroxyisoflavones	antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; geroprotector; human urinary metabolite; phytoestrogen; plant metabolite; tyrosine kinase inhibitor
amphotericin b Amphotericin B: Macrolide antifungal antibiotic produced by Streptomyces nodosus obtained from soil of the Orinoco river region of Venezuela.. amphotericin B : A macrolide antibiotic used to treat potentially life-threatening fungal infections.	3.16	5	0	antibiotic antifungal drug; macrolide antibiotic; polyene antibiotic	antiamoebic agent; antiprotozoal drug; bacterial metabolite
entacapone entacapone: structure given in first source. entacapone : A monocarboxylic acid amide that is N,N-diethylprop-2-enamide in which the hydrogen at position 2 is substituted by a cyano group and the hydrogen at the 3E position is substituted by a 3,4-dihydroxy-5-nitrophenyl group.	2.21	1	0	2-nitrophenols; catechols; monocarboxylic acid amide; nitrile	antidyskinesia agent; antiparkinson drug; central nervous system drug; EC 2.1.1.6 (catechol O-methyltransferase) inhibitor
jasmonic acid jasmonic acid: a derivative of alpha-linolenic acid that has a role in plant response to herbivory analogous to the role of prostanoids in inflammation in mammals;. jasmonic acid : An oxo monocarboxylic acid that is (3-oxocyclopentyl)acetic acid substituted by a (2Z)-pent-2-en-1-yl group at position 2 of the cyclopentane ring.	2.59	2	0	oxo monocarboxylic acid	jasmonates; plant metabolite
butein [no description available]	2.42	2	0	chalcones; polyphenol	antineoplastic agent; antioxidant; EC 1.1.1.21 (aldehyde reductase) inhibitor; geroprotector; hypoglycemic agent; plant metabolite; radiosensitizing agent; tyrosine kinase inhibitor
astaxanthine astaxanthine: a keto form of carotene; pigment in flesh of Scottish salmon (Salmo salar) crustacoa-lobster (Homarus gammarus, flamingo feathers; structure; a carotenoid without vitamin A activity, has shown anti-oxidant and anti-inflammatory activities. astaxanthin : A carotenone that consists of beta,beta-carotene-4,4'-dione bearing two hydroxy substituents at positions 3 and 3' (the 3S,3'S diastereomer). A carotenoid pigment found mainly in animals (crustaceans, echinoderms) but also occurring in plants. It can occur free (as a red pigment), as an ester, or as a blue, brown or green chromoprotein.	2.05	1	0	carotenol; carotenone	animal metabolite; anticoagulant; antioxidant; food colouring; plant metabolite
capsorubin [no description available]	7.31	1	0	carotenone
lutein Lutein: A xanthophyll found in the major LIGHT-HARVESTING PROTEIN COMPLEXES of plants. Dietary lutein accumulates in the MACULA LUTEA.. xanthophyll : A subclass of carotenoids consisting of the oxygenated carotenes.	3.01	2	0	carotenol	food colouring; plant metabolite
sulfuretin sulfuretin: the chalcone C ring closes into a 5 instead of the more typical 6 membered ring leaving a phenyl methane at the 2 position instead of the typical phenyl	2.99	4	0	1-benzofurans
spinasterol spinasterol: RN given refers to alpha-spinasterol ((3beta,5alpha,22E)-isomer)	2.04	1	0	steroid
5,7-dihydroxychromone 5,7-dihydroxychromone: isolated from the roots of Bauhinia hupehara	2.11	1	0	chromones
genistin genistin: glycoside of soy bean isoflavone, gentistein	2.04	1	0	7-hydroxyisoflavones 7-O-beta-D-glucoside
ophiobolin a ophiobolin A: sesterterpene; phytotoxin produced by plant pathogen Helminthosporium maydis; natural product inhibitor of calmodulin; RN refers to (18R)-isomer; structure given in first source. ophiobolin A : A sesterterpenoid that is ophiobolane with a hydroxy group at position 3, oxo groups at positions 5 and 25, double bonds at positions 7-8 and 19-20, and an oxygen link between positions 14 and 18.	1.99	1	0	cyclic ketone; enal; oxaspiro compound; sesterterpenoid; tertiary alcohol
esculetin esculetin: used in filters for absorption of ultraviolet light; structure. esculetin : A hydroxycoumarin that is umbelliferone in which the hydrogen at position 6 is substituted by a hydroxy group. It is used in filters for absorption of ultraviolet light.	3.1	1	0	hydroxycoumarin	antioxidant; plant metabolite; ultraviolet filter
esculin [no description available]	2.01	1	0	beta-D-glucoside; hydroxycoumarin	antioxidant; metabolite
7-hydroxycoumarin 7-oxycoumarin: derivatives have anti-oxidant properties. umbelliferone : A hydroxycoumarin that is coumarin substituted by a hydroxy group ay position 7.	3.51	2	0	hydroxycoumarin	fluorescent probe; food component; plant metabolite
costunolide [no description available]	2.07	1	0	germacranolide; heterobicyclic compound	anthelminthic drug; antiinfective agent; antineoplastic agent; antiparasitic agent; antiviral drug; metabolite
humulene humulene: structure given in first source. (1E,4E,8E)-alpha-humulene : The (1E,4E,8E)-isomer of alpha-humulene.	2.17	1	0	alpha-humulene
oleuropein oleuropein: iridoid isolated from leaves and fruit of Olea and Ligustrum (Oleaceae). oleuropein : A secoiridoid glycoside that is the methyl ester of 3,4-dihydro-2H-pyran-5-carboxylic acid which is substituted at positions 2, 3, and 4 by hydroxy, ethylidene, and carboxymethyl groups, respectively and in which the anomeric hydroxy group at position 2 has been converted into its beta-D-glucoside and the carboxylic acid moiety of the carboxymethyl substituent has been converted to the corresponding 3,4-dihydroxyphenethyl ester (the 2S,3E,4S stereoisomer). The most important phenolic compound present in olive cultivars.	4.4	6	0	beta-D-glucoside; catechols; diester; methyl ester; pyrans; secoiridoid glycoside	anti-inflammatory agent; antihypertensive agent; antineoplastic agent; antioxidant; apoptosis inducer; NF-kappaB inhibitor; nutraceutical; plant metabolite; radical scavenger
zearalenone Zearalenone: (S-(E))-3,4,5,6,8,10-Hexahydro-14,16-dihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione. One of a group of compounds known under the general designation of resorcylic acid lactones. Cis, trans, dextro and levo forms have been isolated from the fungus Gibberella zeae (formerly Fusarium graminearum). They have estrogenic activity, cause toxicity in livestock as feed contaminant, and have been used as anabolic or estrogen substitutes.. zearalenone : A macrolide comprising a fourteen-membered lactone fused to 1,3-dihydroxybenzene; a potent estrogenic metabolite produced by some Giberella species.	7.41	1	0	macrolide; resorcinols	fungal metabolite; mycoestrogen
agathisflavone agathisflavone: bis-apigenin coupled at 6 and 8 positions; isolated from the plant Canarium manii; has hepatoprotective activity against carbon tetrachloride-induced hepatotoxicity. agathisflavone : A biflavonoid that is obtained by oxidative coupling of two molecules of apigenin resulting in a bond between positions C-6 and C-8 of the two chromene rings.	2.17	1	0	biaryl; biflavonoid; hydroxyflavone	antineoplastic agent; antiviral agent; hepatoprotective agent; metabolite
amentoflavone [no description available]	2.75	3	0	biflavonoid; hydroxyflavone; ring assembly	angiogenesis inhibitor; antiviral agent; cathepsin B inhibitor; P450 inhibitor; plant metabolite
axillarin axillarin: isolated from Pulicaria crispa or Filifdium sibiricum; structure given in first source. axillarin : A dimethoxyflavone that is the 3,6-dimethyl ether derivative of quercetagetin.	2	1	0	dimethoxyflavone; tetrahydroxyflavone	plant metabolite
baicalein [no description available]	4.56	7	0	trihydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antibacterial agent; anticoronaviral agent; antifungal agent; antineoplastic agent; antioxidant; apoptosis inducer; EC 1.13.11.31 (arachidonate 12-lipoxygenase) inhibitor; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; EC 4.1.1.17 (ornithine decarboxylase) inhibitor; ferroptosis inhibitor; geroprotector; hormone antagonist; plant metabolite; prostaglandin antagonist; radical scavenger
chrysin chrysin : A dihydroxyflavone in which the two hydroxy groups are located at positions 5 and 7.	5.39	10	0	7-hydroxyflavonol; dihydroxyflavone	anti-inflammatory agent; antineoplastic agent; antioxidant; EC 2.7.11.18 (myosin-light-chain kinase) inhibitor; hepatoprotective agent; plant metabolite
datiscetin datiscetin : A tetrahydroxyflavone that is 7-hydroxyflavonol bearing two additional hydroxy substituents at positions 2' and 5.	2.13	1	0	7-hydroxyflavonol; tetrahydroxyflavone
3,7,4'-trihydroxyflavone 3,7,4'-trihydroxyflavone: structure in first source	2.52	2	0	hydroxyflavan
fisetin [no description available]	4.57	7	0	3'-hydroxyflavonoid; 7-hydroxyflavonol; tetrahydroxyflavone	anti-inflammatory agent; antioxidant; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; geroprotector; metabolite; plant metabolite
galangin 5,7-dihydroxyflavonol: antimicrobial from the twigs of Populus nigra x Populus deltoides; structure in first source. galangin : A 7-hydroxyflavonol with additional hydroxy groups at positions 3 and 5 respectively; a growth inhibitor of breast tumor cells.	4.25	5	0	7-hydroxyflavonol; trihydroxyflavone	antimicrobial agent; EC 3.1.1.3 (triacylglycerol lipase) inhibitor; plant metabolite
gossypin gossypin: do not confuse with gossypin(e) which is synonym for choline. gossypin : A glycosyloxyflavone that is gossypetin attached to a beta-D-glucopyranosyl residue at position 8 via a glycosidic linkage.	2.5	2	0	7-hydroxyflavonol; glycosyloxyflavone; monosaccharide derivative; pentahydroxyflavone	neuroprotective agent; plant metabolite
hispidulin hispidulin : A monomethoxyflavone that is scutellarein methylated at position 6.	3.64	2	0	monomethoxyflavone; trihydroxyflavone	anti-inflammatory agent; anticonvulsant; antineoplastic agent; antioxidant; apoptosis inducer; plant metabolite
gartanin gartanin : A member of the class of xanthones that is 9H-xanthen-9-one substituted by hydroxy groups at positions 1, 3, 5 and 8 and prenyl groups at positions 2 and 4.	2.11	1	0	polyphenol; xanthones	antineoplastic agent; plant metabolite
gentisin gentisin: a hydroxyxanthone from methanol extract of Gentianae (Gentian?) radix and Calophyllum. gentisin : A member of the class of xanthones that is 9H-xanthen-9-one substituted by hydroxy groups at positions 1 and 7 and a methoxy group at position 3.	2.17	1	0	aromatic ether; polyphenol; xanthones	plant metabolite
isogentisin isogentisin: found in plants such as Guttiferae & Gentianaceae.; structure. isogentisin : A member of the class of xanthones that is 9H-xanthen-9-one substituted by hydroxy groups at positions 1 and 3 and a methoxy group at position 7.	2.17	1	0	aromatic ether; polyphenol; xanthones	EC 1.4.3.4 (monoamine oxidase) inhibitor; plant metabolite
hyperoside quercetin 3-O-beta-D-galactopyranoside : A quercetin O-glycoside that is quercetin with a beta-D-galactosyl residue attached at position 3. Isolated from Artemisia capillaris, it exhibits hepatoprotective activity.	3.6	8	0	beta-D-galactoside; monosaccharide derivative; quercetin O-glycoside; tetrahydroxyflavone	hepatoprotective agent; plant metabolite
mangiferin shamimin: isolated from the leaves of Bombax ceiba; structure in first source	3.31	6	0	C-glycosyl compound; xanthones	anti-inflammatory agent; antioxidant; hypoglycemic agent; plant metabolite
mangostin mangostin: xanthone from rind of Garcinia mangostana Linn. fruit. alpha-mangostin : A member of the class of xanthones that is 9H-xanthene substituted by hydroxy group at positions 1, 3 and 6, a methoxy group at position 7, an oxo group at position 9 and prenyl groups at positions 2 and 8. Isolated from the stems of Cratoxylum cochinchinense, it exhibits antioxidant, antimicrobial and antitumour activities.	2.49	2	0	aromatic ether; phenols; xanthones	antimicrobial agent; antineoplastic agent; antioxidant; plant metabolite
3-methylquercetin isorhamnetin : A monomethoxyflavone that is quercetin in which the hydroxy group at position 3' is replaced by a methoxy group.	3.49	7	0	7-hydroxyflavonol; monomethoxyflavone; tetrahydroxyflavone	anticoagulant; EC 1.14.18.1 (tyrosinase) inhibitor; metabolite
kaempferide kaempferide: structure in first source. kaempferide : A monomethoxyflavone that is the 4'-O-methyl derivative of kaempferol.	2.06	1	0	7-hydroxyflavonol; monomethoxyflavone; trihydroxyflavone	antihypertensive agent; metabolite
morin morin: a light yellowish pigment found in the wood of old fustic (Chlorophora tinctoria). morin : A pentahydroxyflavone that is 7-hydroxyflavonol bearing three additional hydroxy substituents at positions 2' 4' and 5.	3.13	5	0	7-hydroxyflavonol; pentahydroxyflavone	angiogenesis modulating agent; anti-inflammatory agent; antibacterial agent; antihypertensive agent; antineoplastic agent; antioxidant; EC 5.99.1.2 (DNA topoisomerase) inhibitor; hepatoprotective agent; metabolite; neuroprotective agent
myricetin [no description available]	6.13	37	0	7-hydroxyflavonol; hexahydroxyflavone	antineoplastic agent; antioxidant; cyclooxygenase 1 inhibitor; food component; geroprotector; hypoglycemic agent; plant metabolite
myricitrin myricitrin: isolated from root bark of Myrica cerifera L.; structure. myricitrin : A glycosyloxyflavone that consists of myricetin attached to a alpha-L-rhamnopyranosyl residue at position 3 via a glycosidic linkage. Isolated from Myrica cerifera, it exhibits anti-allergic activity.	2.94	4	0	alpha-L-rhamnoside; glycosyloxyflavone; monosaccharide derivative; pentahydroxyflavone	anti-allergic agent; EC 1.14.13.39 (nitric oxide synthase) inhibitor; EC 2.7.11.13 (protein kinase C) inhibitor; plant metabolite
orientin orientin: structure given in first source; RN given refers to the (D-glucopyranosyl)-isomer. orientin : A C-glycosyl compound that is luteolin substituted by a beta-D-glucopyranosyl moiety at position 8.	2.03	1	0	3'-hydroxyflavonoid; C-glycosyl compound; tetrahydroxyflavone	antioxidant; metabolite
patuletin patuletin: structure given in first source; inhibits aldose reductase in rat lens. patuletin : A trimethoxyflavone that is quercetagetin methylated at position 6.	2.73	3	0	flavonols; monomethoxyflavone; pentahydroxyflavone	analgesic; antioxidant; EC 1.1.1.21 (aldehyde reductase) inhibitor; lipoxygenase inhibitor; metabolite
quercetagetin quercetagetin: structure given in first source; inhibits aldose reductase in rat lens. quercetagetin : A hexahydroxyflavone that is flavone substituted by hydroxy groups at positions 3, 5, 6, 7, 3' and 4' respectively.	2.06	1	0	flavonols; hexahydroxyflavone	antioxidant; antiviral agent; plant metabolite
robinetin robinetin: structure given in first source. robinetin : A pentahydroxyflavone that is flavone substituted by hydroxy groups at positions 3, 7, 3, 4' and 5'.	2.13	1	0	7-hydroxyflavonol; pentahydroxyflavone	plant metabolite
scutellarein scutellarein: aglycone of scutellarin from Scutellaria baicalensis; carthamidin is 2S isomer of scutellarein; do not confuse with isoscutellarein and/or isocarthamidin which are respective regioisomers, or with the scutelarin protein. scutellarein : Flavone substituted with hydroxy groups at C-4', -5, -6 and -7.	2.49	2	0	tetrahydroxyflavone	metabolite
tamarixetin tamarixetin: isolated from Costsus spicatus. tamarixetin : A monomethoxyflavone that is quercetin methylated at position O-4'. Isolated from Cyperus teneriffae.	2.06	1	0	7-hydroxyflavonol; monomethoxyflavone; tetrahydroxyflavone	antioxidant; metabolite
tricetin tricetin : Flavone hydroxylated at positions 3', 4', 5, 5' and 7.	2.05	1	0	pentahydroxyflavone	antineoplastic agent; metabolite
tricin tricin: from Spartina cynosuroides and other plants; structure	2.04	1	0	3'-methoxyflavones; dimethoxyflavone; trihydroxyflavone	EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; metabolite
wogonin wogonin: structure in first source. wogonin : A dihydroxy- and monomethoxy-flavone in which the hydroxy groups are positioned at C-5 and C-7 and the methoxy group is at C-8.	2.52	2	0	dihydroxyflavone; monomethoxyflavone	angiogenesis inhibitor; antineoplastic agent; cyclooxygenase 2 inhibitor; plant metabolite
daidzein [no description available]	9.3	5	0	7-hydroxyisoflavones	antineoplastic agent; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; phytoestrogen; plant metabolite
isorhapontin isorhapontin: from spruce (Picea); structure in first source	2	1	0	glycoside; stilbenoid
trans-2,3',4,5'-tetrahydroxystilbene trans-2,3',4,5'-tetrahydroxystilbene: hydroxystilbene oxyresveratrol	2.11	1	0	stilbenoid
polydatin trans-piceid : A stilbenoid that is trans-resveratrol substituted at position 3 by a beta-D-glucosyl residue.	2.07	1	0	beta-D-glucoside; monosaccharide derivative; polyphenol; stilbenoid	anti-arrhythmia drug; antioxidant; geroprotector; hepatoprotective agent; metabolite; nephroprotective agent; potassium channel modulator
pterostilbene [no description available]	2.07	1	0	diether; methoxybenzenes; stilbenol	anti-inflammatory agent; antineoplastic agent; antioxidant; apoptosis inducer; hypoglycemic agent; neuroprotective agent; neurotransmitter; plant metabolite; radical scavenger
epsilon-viniferin epsilon-viniferin: stilbene dimer; isolated from the Oriental medicinal plant Vitis coignetiae; structure given in first source. (-)-trans-epsilon-viniferin : A stilbenoid that is the (-)-trans-stereoisomer of epsilon-viniferin, obtained by cyclodimerisation of trans-resveratrol.	2.07	1	0	1-benzofurans; polyphenol; stilbenoid	metabolite
cynarine cynarine: active principle of the artichoke; functions primarily as a cholagogue and choleretic and also as antilipemic agent	2.07	1	0	alkyl caffeate ester; quinic acid	plant metabolite
echinacoside echinacoside: from Buddleja species; has antihepatotoxic activity	2.13	1	0	oligosaccharide
forsythiaside forsythiaside: RN given refers to (E)-isomer; structure given in first source; from the unripe fruit of Forsythia suspensa (qinglianquiao)	2.11	1	0	hydroxycinnamic acid
3,4-di-o-caffeoylquinic acid 3,4-di-O-caffeoylquinic acid: isolated from Siphonostegia chinensis	2.03	1	0	quinic acid
caffeic acid phenethyl ester phenethyl caffeate : An alkyl caffeate ester in which 2-phenylethyl is the alkyl component.	2.46	2	0	alkyl caffeate ester	anti-inflammatory agent; antibacterial agent; antineoplastic agent; antioxidant; antiviral agent; immunomodulator; metabolite; neuroprotective agent
rosmarinic acid rosmarinic acid: RN given refers to parent cpd; promote OT project. (R)-rosmarinic acid : A stereoisomer of rosmarinic acid having (R)-configuration.. rosmarinic acid : The 1-carboxy-2-(2,4-dihydroxyphenyl)ethyl ester of trans-caffeic acid.	4.03	13	0	rosmarinic acid	geroprotector; plant metabolite
salvianolic acid a salvianolic acid A: a nootropic depside from Salvia miltiorrhizia	2.11	1	0	stilbenoid
shogaol shogaol: from ginger, ZINGIBER OFFICINALE; less mutagenic than GINGEROL; structure given in first source	2.1	1	0	enone; monomethoxybenzene; phenols
acteoside acteoside: a protein kinase C inhibitor with hepatoprotective, anti-asthmatic, and analgesic activities; a phenylethanoid glycoside related to isoacteoside; from leaves of Lippia multiflora (Verbenaceae). acteoside : A glycoside that is the alpha-L-rhamnosyl-(1->3)-beta-D-glucoside of hydroxytyrosol in which the hydroxy group at position 4 of the glucopyranosyl moiety has undergone esterification by formal condensation with trans-caffeic acid.	2.45	2	0	catechols; cinnamate ester; disaccharide derivative; glycoside; polyphenol	anti-inflammatory agent; antibacterial agent; antileishmanial agent; neuroprotective agent; plant metabolite
wedelolactone wedelolactone: antihepatotoxic coumestan from Eclipta prostrata and Wedelia calendulacea (both Asteraceae); structure given in first source. wedelolactone : A member of the class of coumestans that is coumestan with hydroxy substituents as positions 1, 8 and 9 and a methoxy substituent at position 3.	2.82	3	0	aromatic ether; coumestans; delta-lactone; polyphenol	antineoplastic agent; apoptosis inducer; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; hepatoprotective agent; metabolite
ellagic acid [no description available]	8.92	153	0	catechols; cyclic ketone; lactone; organic heterotetracyclic compound; polyphenol	antioxidant; EC 1.14.18.1 (tyrosinase) inhibitor; EC 2.3.1.5 (arylamine N-acetyltransferase) inhibitor; EC 2.4.1.1 (glycogen phosphorylase) inhibitor; EC 2.5.1.18 (glutathione transferase) inhibitor; EC 2.7.1.127 (inositol-trisphosphate 3-kinase) inhibitor; EC 2.7.1.151 (inositol-polyphosphate multikinase) inhibitor; EC 2.7.4.6 (nucleoside-diphosphate kinase) inhibitor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; EC 5.99.1.2 (DNA topoisomerase) inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; food additive; fungal metabolite; geroprotector; plant metabolite; skin lightening agent
3,3',4-o-trimethylellagic acid 3,7,8-tri-O-methylellagic acid: structure given in first source	2.03	1	0	tannin
coenzyme q10 coenzyme Q10: Ubiquinone ring with a chain of 10 isoprene units; redox equilibrium with ubiqunol serving in mitochondrial inner membrane to transfer electrons; presence during reconstitution of acetylcholine receptor into phospholipid vesicles yields vesicles active in catalyzing carbamylcholine-sensitive Na+ flux; coenzyme Q10 depletion has been noted with use of statins. coenzyme Q10 : A ubiquinone having a side chain of 10 isoprenoid units. In the naturally occurring isomer, all isoprenyl double bonds are in the E- configuration.	2	1	0	ubiquinones	antioxidant; ferroptosis inhibitor; human metabolite
tectochrysin tectochrysin: structure in first source. tectochrysin : A monohydroxyflavone that is flavone substituted by a hydroxy group at position 4 and a methoxy group at position 7 respectively.	2.13	1	0	monohydroxyflavone; monomethoxyflavone	antidiarrhoeal drug; antineoplastic agent; plant metabolite
cerulenin Cerulenin: An epoxydodecadienamide isolated from several species, including ACREMONIUM, Acrocylindrum, and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function.. cerulenin : An epoxydodecadienamide isolated from several species, including Acremonium, Acrocylindrum and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function.	2.05	1	0	epoxide; monocarboxylic acid amide	antifungal agent; antiinfective agent; antilipemic drug; antimetabolite; antimicrobial agent; fatty acid synthesis inhibitor
astragalin kaempferol-3-O-glucoside: isolated from the pit of Mahkota dewa; structure in first source. kaempferol 3-O-beta-D-glucoside : A kaempferol O-glucoside in which a glucosyl residue is attached at position 3 of kaempferol via a beta-glycosidic linkage.	3.46	7	0	beta-D-glucoside; kaempferol O-glucoside; monosaccharide derivative; trihydroxyflavone	plant metabolite; trypanocidal drug
kaempferol-3-o-galactoside kaempferol-3-O-galactoside: isolated from Ardisia pusilla; RN given refers to (3-(beta-D-galactopyranosyloxy))-isomer. kaempferol 3-O-beta-D-galactoside : A beta-D-galactoside compound with a 4',5,7-trihydroxychromen-3-yl group at the anomeric position.	2.42	2	0	beta-D-galactoside; glycosyloxyflavone; monosaccharide derivative; trihydroxyflavone	antifungal agent; plant metabolite
kaempferol 3-o-sophoroside kaempferol 3-O-sophoroside: isolated from leaves of Cassia alata. kaempferol 3-O-beta-D-glucosyl-(1->2)-beta-D-glucoside : A sophoroside that is kaempferol attached to a beta-D-sophorosyl residue at position 3 via a glycosidic linkage.	2.13	1	0	sophoroside; trihydroxyflavone	plant metabolite
4-acetamido-4'-isothiocyanatostilbene-2,2'-disulfonic acid 4-Acetamido-4'-isothiocyanatostilbene-2,2'-disulfonic Acid: A non-penetrating amino reagent (commonly called SITS) which acts as an inhibitor of anion transport in erythrocytes and other cells.	2.66	3	0	stilbenoid
4-hydroxyestradiol 4-hydroxyestradiol: catechol estrogen. 4-hydroxy-17beta-estradiol : A 4-hydroxy steroid that consists of 17beta-estradiol having an additional hydroxy group at position 4.	3.1	1	0	4-hydroxy steroid	metabolite
11-ketotestosterone 11-ketotestosterone: RN given refers to cpd without isomeric designation. 11-oxotestosterone : A 3-oxo Delta(4)-steroid that is testosterone carrying an additional oxo substituent at position 11.	2.15	1	0	11-oxo steroid; 17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; androstanoid	androgen; human metabolite; marine xenobiotic metabolite
isotretinoin Isotretinoin: A topical dermatologic agent that is used in the treatment of ACNE VULGARIS and several other skin diseases. The drug has teratogenic and other adverse effects.. isotretinoin : A retinoic acid that is all-trans-retinoic acid in which the double bond which is alpha,beta- to the carboxy group is isomerised to Z configuration. A synthetic retinoid, it is used for the treatment of severe cases of acne and other skin diseases.	3.54	2	0	retinoic acid	antineoplastic agent; keratolytic drug; teratogenic agent
misoprostol Misoprostol: A synthetic analog of natural prostaglandin E1. It produces a dose-related inhibition of gastric acid and pepsin secretion, and enhances mucosal resistance to injury. It is an effective anti-ulcer agent and also has oxytocic properties.. misoprostol : A diastereoisomeric mixture composed of approximately equal amounts of a double racemate of four of the sixteen possible diastereoisomers of methyl (13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate that is racemic prostaglandin E1 which is lacking the hydroxy group at position 15, but which has an additional hydroxy group at position 16. It is a synthetic prostaglandin E1 analogue, used in the treatment of gastric and duodenal ulcers. A weak abortifacient, it is also used for cervical ripening prior to surgical termination of pregnancy. The (11R,16S)-diastereoisomer is the pharmacologically active form.	2.06	1	0
triprolidine Triprolidine: Histamine H1 antagonist used in allergic rhinitis; ASTHMA; and URTICARIA. It is a component of COUGH and COLD medicines. It may cause drowsiness.. triprolidine : An N-alkylpyrrolidine that is acrivastine in which the pyridine ring is lacking the propenoic acid substituent. It is a sedating antihistamine that is used (generally as the monohydrochloride monohydrate) for the relief of the symptoms of uticaria, rhinitis, and various pruritic skin disorders.	2.1	1	0	N-alkylpyrrolidine; olefinic compound; pyridines	H1-receptor antagonist
thromboxane b2 Thromboxane B2: A stable, physiologically active compound formed in vivo from the prostaglandin endoperoxides. It is important in the platelet-release reaction (release of ADP and serotonin).. thromboxane B2 : A member of the class of thromboxanes B that is (5Z,13E)-thromboxa-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15.	3.07	5	0	thromboxanes B	human metabolite; mouse metabolite
4-hydroxy-2-nonenal 4-hydroxy-2-nonenal: cytotoxic product from peroxidation of liver microsomal lipids; RN given refers to cpd without isomeric designation. 4-hydroxynon-2-enal : An enal consisting of non-2-ene having an oxo group at the 1-position and a hydroxy group at the 4-position.. 4-hydroxynonenal : A monounsaturated fatty aldehyde that is nonanal that has undergone dehydrogenation to introduce a double bond at any position in the aliphatic chain and in which a hydrogen at position 4 has been replaced by a hydroxy group.	2.21	1	0	4-hydroxynon-2-enal; 4-hydroxynonenal
1-monooleoyl-rac-glycerol Peceol: lipid excipient containing readily dispersible mixture of mono- & diglycerides of oleic acid. 1-oleoylglycerol : A 1-monoglyceride where the acyl group is oleoyl.. monooleoylglycerol : A monoglyceride in which the acyl group is oleoyl with the position of acylation unspecified.	2.48	2	0	1-acylglycerol 18:1; monooleoylglycerol	plant metabolite
sphingosine 1-phosphate sphingosine 1-phosphate: RN given refers to (R-(R,S-(E)))-isomer; RN for cpd without isomeric designation not available 8/89. sphingosine 1-phosphate : A phosphosphingolipid that consists of sphingosine having a phospho group attached at position 1	1.99	1	0	sphingoid 1-phosphate	mouse metabolite; signalling molecule; sphingosine-1-phosphate receptor agonist; T-cell proliferation inhibitor; vasodilator agent
hyodeoxycholic acid hyodeoxycholic acid: differs from deoxycholic acid in that the 6 alpha-OH is in the 12 position in the former; RN given refers to (3alpha,5beta,6alpha)-isomer. hyodeoxycholic acid : A member of the class of 5beta-cholanic acids that is (5beta)-cholan-24-oic acid substituted by alpha-hydroxy groups at positions 3 and 6.	3.1	1	0	5beta-cholanic acids; 6alpha,20xi-murideoxycholic acid; bile acid; C24-steroid	human metabolite; mouse metabolite
codeine [no description available]	3.54	2	0	morphinane alkaloid; organic heteropentacyclic compound	antitussive; drug allergen; environmental contaminant; opioid analgesic; opioid receptor agonist; prodrug; xenobiotic
methyl linoleate [no description available]	2	1	0	fatty acid methyl ester	plant metabolite
quercetin [no description available]	2.13	1	0
3-amino-1,4-dimethyl-5h-pyrido(4,3-b)indole 3-amino-1,4-dimethyl-5H-pyrido(4,3-b)indole: structure	1.97	1	0	pyridoindole
3-amino-1-methyl-5h-pyrido(4,3-b)indole 3-amino-1-methyl-5H-pyrido(4,3-b)indole: structure	1.97	1	0	pyridoindole
dihydrocodeine dihydrocodeine: RN refers to parent cpd(5alpha,6alpha)-isomer	2.1	1	0	morphinane alkaloid
diminazene aceturate diminazene diaceturate : An N-acetylglycinate salt resulting from the reaction of diminazene with 2 mol eq. of N-acetylglycine.	2.21	1	0	N-acetylglycinate salt	antiparasitic agent; trypanocidal drug
hydromorphone Hydromorphone: An opioid analgesic made from MORPHINE and used mainly as an analgesic. It has a shorter duration of action than morphine.. hydromorphone : A morphinane alkaloid that is a hydrogenated ketone derivative of morphine. A semi-synthetic drug, it is a centrally acting pain medication of the opioid class.	3.1	1	0	morphinane alkaloid; organic heteropentacyclic compound	mu-opioid receptor agonist; opioid analgesic
nalmefene nalmefene: RN given refers to 5-alpha isomer	3.1	1	0	morphinane alkaloid
nalorphine Nalorphine: A narcotic antagonist with some agonist properties. It is an antagonist at mu opioid receptors and an agonist at kappa opioid receptors. Given alone it produces a broad spectrum of unpleasant effects and it is considered to be clinically obsolete.	3.1	1	0	morphinane alkaloid
naloxone Naloxone: A specific opiate antagonist that has no agonist activity. It is a competitive antagonist at mu, delta, and kappa opioid receptors.. naloxone : A synthetic morphinane alkaloid that is morphinone in which the enone double bond has been reduced to a single bond, the hydrogen at position 14 has been replaced by a hydroxy group, and the methyl group attached to the nitrogen has been replaced by an allyl group. A specific opioid antagonist, it is used (commonly as its hydrochloride salt) to reverse the effects of opioids, both following their use of opioids during surgery and in cases of known or suspected opioid overdose.	4.03	4	0	morphinane alkaloid; organic heteropentacyclic compound; tertiary alcohol	antidote to opioid poisoning; central nervous system depressant; mu-opioid receptor antagonist
oxycodone Oxycodone: A semisynthetic derivative of CODEINE.. oxycodone : A semisynthetic opioid of formula C18H21NO4 that is derived from thebaine. It is a moderately potent opioid analgesic, generally used for relief of moderate to severe pain.	3.54	2	0	organic heteropentacyclic compound; semisynthetic derivative	antitussive; mu-opioid receptor agonist; opioid analgesic
oxymorphone Oxymorphone: An opioid analgesic with actions and uses similar to those of MORPHINE, apart from an absence of cough suppressant activity. It is used in the treatment of moderate to severe pain, including pain in obstetrics. It may also be used as an adjunct to anesthesia. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1092)	3.1	1	0	morphinane alkaloid
sirolimus Sirolimus: A macrolide compound obtained from Streptomyces hygroscopicus that acts by selectively blocking the transcriptional activation of cytokines thereby inhibiting cytokine production. It is bioactive only when bound to IMMUNOPHILINS. Sirolimus is a potent immunosuppressant and possesses both antifungal and antineoplastic properties.. sirolimus : A macrolide lactam isolated from Streptomyces hygroscopicus consisting of a 29-membered ring containing 4 trans double bonds, three of which are conjugated. It is an antibiotic, immunosupressive and antineoplastic agent.	2.11	1	0	antibiotic antifungal drug; cyclic acetal; cyclic ketone; ether; macrolide lactam; organic heterotricyclic compound; secondary alcohol	antibacterial drug; anticoronaviral agent; antineoplastic agent; bacterial metabolite; geroprotector; immunosuppressive agent; mTOR inhibitor
6alpha-hydroxy-17beta-estradiol 6alpha-hydroxy-17beta-estradiol : A 4-hydroxy steroid that consists of 17beta-estradiol bearing an additional 6alpha-hydroxy substituent.	3.1	1	0	6alpha-hydroxy steroid
morphine Meconium: The thick green-to-black mucilaginous material found in the intestines of a full-term fetus. It consists of secretions of the INTESTINAL GLANDS; BILE PIGMENTS; FATTY ACIDS; AMNIOTIC FLUID; and intrauterine debris. It constitutes the first stools passed by a newborn.	4	4	0	morphinane alkaloid; organic heteropentacyclic compound; tertiary amino compound	anaesthetic; drug allergen; environmental contaminant; geroprotector; mu-opioid receptor agonist; opioid analgesic; plant metabolite; vasodilator agent; xenobiotic
rutin quercetin-3-O-rutinoside: structure in first source	3.73	2	0	flavonoids; glycoside
2-methylthio-atp 2-methylthio-ATP: purinergic receptors agonist; relaxes mammalian gut preparations; structure given in first source	1.99	1	0
benzphetamine Benzphetamine: A sympathomimetic agent with properties similar to DEXTROAMPHETAMINE. It is used in the treatment of obesity. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1222). benzphetamine : Dextroamphetamine in which the the hydrogens attached to the amino group are substituted by a methyl and a benzyl group. A sympathomimetic agent with properties similar to dextroamphetamine, it is used as its hydrochloride salt in the treatment of obesity.	1.95	1	0	amphetamines; tertiary amine	adrenergic uptake inhibitor; appetite depressant; dopamine uptake inhibitor; sympathomimetic agent
clobetasol Clobetasol: A derivative of PREDNISOLONE with high glucocorticoid activity and low mineralocorticoid activity. Absorbed through the skin faster than FLUOCINONIDE, it is used topically in treatment of PSORIASIS but may cause marked adrenocortical suppression.. clobetasol : A 3-oxo-Delta(1),Delta(4)-steroid that is 16beta-methylpregna-1,4-diene-3,20-dione bearing hydroxy groups at the 11beta and 17alpha positions, fluorine at position 9, and a chlorine substituent at position 21. It is used as its 17alpha-propionate ester to treat various skin disorders, including exzema and psoriasis.	2.41	1	0	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 3-oxo-Delta(1),Delta(4)-steroid; chlorinated steroid; fluorinated steroid; glucocorticoid; tertiary alpha-hydroxy ketone	anti-inflammatory drug; SMO receptor agonist
deamino arginine vasopressin Deamino Arginine Vasopressin: A synthetic analog of the pituitary hormone, ARGININE VASOPRESSIN. Its action is mediated by the VASOPRESSIN receptor V2. It has prolonged antidiuretic activity, but little pressor effects. It also modulates levels of circulating FACTOR VIII and VON WILLEBRAND FACTOR.	2.38	2	0	heterodetic cyclic peptide	diagnostic agent; renal agent; vasopressin receptor agonist
fluprostenol fluprostenol: synthetic prostaglandin F 2 alpha analog used as an abortifacient; RN given refers to ((1alpha(Z),2beta(1E,3R*),3alpha,5alpha)-(+-))-isomer. fluprostenol : An organofluorine compound that is racemic prostaglandin F2alpha in which the pentyl group is replaced by a 3-(trifluoromethyl)phenoxymethyl group. A synthetic analogue of prostaglandin F2alpha, ophthalmic solutions of its isopropyl ester prodrug, travoprost, are used as a topical medication for controlling the progression of open-angle glaucoma and ocular hypertension, by reducing intraocular pressure. The isopropyl ester group of travoprost is hydrolysed to the biologically active free acid by esterases in the cornea.	2	1	0	(trifluoromethyl)benzenes; hydroxy monocarboxylic acid; prostaglandins Falpha	abortifacient; antiglaucoma drug; antihypertensive agent; female contraceptive drug; prostaglandin receptor agonist
herbimycin herbimycin: herbicidal antibiotic produced by Streptomyces sp.; see also herbimycin B; structure for herbimycin A in second source. herbimycin : A 19-membered macrocyle incorporating a benzoquinone ring and a lactam functionality. It is an ansamycin antibiotic that induces apoptosis and displays antitumour effects.	2	1	0	1,4-benzoquinones; lactam; macrocycle	antimicrobial agent; apoptosis inducer; herbicide; Hsp90 inhibitor; tyrosine kinase inhibitor
preclamol preclamol: centrally acting dopamine receptor agonist with selectivity for autoreceptors	1.99	1	0
lysophosphatidic acid lysophosphatidic acid: RN given refers to parent cpd. 1-oleoyl-sn-glycerol 3-phosphate : A 1-acyl-sn-glycerol 3-phosphate having oleoyl as the 1-O-acyl group.. lysophosphatidic acid : A member of the class of lysophosphatidic acids obtained by hydrolytic removal of one of the two acyl groups of any phosphatidic acid. A 'closed' class.	2.02	1	0	1-acyl-sn-glycerol 3-phosphate
lysophosphatidylcholines lysophosphatidylcholine : An acylglycerophosphocholine resulting from partial hydrolysis of a phosphatidylcholine, which removes one of the fatty acyl groups. The structure is depicted in the image where R1 = acyl, R2 = H or where R1 = H, R2 = acyl.	2.67	3	0	1-O-acyl-sn-glycero-3-phosphocholine
cytochalasin b Cytochalasin B: A cytotoxic member of the CYTOCHALASINS.. cytochalasin B : An organic heterotricyclic compound, that is a mycotoxin which is cell permeable an an inhibitor of cytoplasmic division by blocking the formation of contractile microfilaments.	4.22	18	0	cytochalasin; lactam; lactone; organic heterotricyclic compound	actin polymerisation inhibitor; metabolite; mycotoxin; platelet aggregation inhibitor
nalbuphine Nalbuphine: A narcotic used as a pain medication. It appears to be an agonist at KAPPA RECEPTORS and an antagonist or partial agonist at MU RECEPTORS.	3.1	1	0	organic heteropentacyclic compound	mu-opioid receptor antagonist; opioid analgesic
pd 123319 PD123319 : An imidazopyridine consisting of 4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine having 4-(dimethylamino)-3-methylbenzyl, diphenylacetyl and carboxy and groups at positions 1, 5 and 6 respectively	2.07	1	0	imidazopyridine	angiotensin receptor antagonist; endothelin receptor antagonist; vasoconstrictor agent
calyculin a calyculin A: RN given refers to (5S-(5alpha(2R(1S,3S,4S,5R,6R,7E,9E,11E,13Z),3R),7beta(E(S)),*beta,9alpha))-isomer	1.99	1	0
kn 93 KN 93: reduces dopamine content in PC12h cells. KN-93 : A sulfonamide resulting from the formal condensation of p-methoxybenzenesulfonic acid with the anilino nitrogen of 2-(aminomethyl)-N-(2-hydroxyethyl)aniline in which the hydrogens of the primary amino group have been replaced by methyl and p-chlorocinnamyl groups. KN-93 is a selective inhibitor of Ca(2+)/calmodulin-dependent protein kinase II.	2.01	1	0	monochlorobenzenes; monomethoxybenzene; primary alcohol; sulfonamide; tertiary amino compound	EC 2.7.11.17 (Ca(2+)/calmodulin-dependent protein kinase) inhibitor; geroprotector
1,2-oleoylphosphatidylcholine 1,2-oleoylphosphatidylcholine: RN given refers to (Z,Z)-isomer. dioleoyl phosphatidylcholine : A phosphatidylcholine in which the phosphatidyl acyl groups are both oleoyl.	2.77	3	0	phosphatidylcholine(1+)
broussonin b broussonin B: structure in first source	3.31	1	0
cinnamyl alcohol cinnamyl alcohol: RN given refers to parent cpd without isomeric designation. (E)-cinnamyl alcohol : The E (trans) stereoisomer of cinnamyl alcohol.. cinnamyl alcohol : A primary alcohol comprising an allyl core with a hydroxy substituent at the 1-position and a phenyl substituent at the 3-position (geometry of the C=C bond unspecified).	3.1	1	0	cinnamyl alcohol	plant metabolite
desoxyrhaponticin [no description available]	2	1	0	glycoside; stilbenoid
kaempferol 3-o-rhamnoside kaempferol 3-O-rhamnoside: from apple (Malus domestica) leaves; structure in first source. afzelin : A glycosyloxyflavone that is kaempferol attached to an alpha-L-rhamnosyl residue at position 3 via a glycosidic linkage.	3.2	5	0	glycosyloxyflavone; monosaccharide derivative; trihydroxyflavone	anti-inflammatory agent; antibacterial agent; plant metabolite
syringin syringin: a phenylpropanoid glycoside; see also eleutherosides & lyoniside for eleutheroside A: 474-58-8. syringin : A monosaccharide derivative that is trans-sinapyl alcohol attached to a beta-D-glucopyranosyl residue at position 1 via a glycosidic linkage.	2.79	3	0	beta-D-glucoside; dimethoxybenzene; monosaccharide derivative; primary alcohol	hepatoprotective agent; plant metabolite
ethyl caffeate (E)-ethyl 3-(3,4-dihydroxyphenyl)prop-2-enoate: structure in first source. ethyl trans-caffeate : An ethyl ester resulting from the formal condensation of the carboxy group of trans-caffeic acid with ethanol.	2.53	2	0	alkyl caffeate ester; ethyl ester; hydroxycinnamic acid	anti-inflammatory agent; antineoplastic agent; metabolite
fustin fustin : A dihydroflavonol that is the 2,3-dihydro derivative of fisetin.. tetrahydroxyflavanone : A hydroxyflavanone with atleast four hydroxy substituents.	2.8	3	0
glycitein glycitein : A methoxyisoflavone that is isoflavone substituted by a methoxy group at position 6 and hydroxy groups at positions 7 and 4'. It has been isolated from the mycelia of the fungus Cordyceps sinensis.	2.04	1	0	7-hydroxyisoflavone; methoxyisoflavone	fungal metabolite; phytoestrogen; plant metabolite
ginnalin a ginnalin A: isolated from Acer pycnanthum; structure in first source	3.83	10	0
andrographolide [no description available]	2.6	1	0	carbobicyclic compound; gamma-lactone; labdane diterpenoid; primary alcohol; secondary alcohol	anti-HIV agent; anti-inflammatory drug; antineoplastic agent; metabolite
isorhapontigenin isorhapontigenin: isolated from the seeds of Aiphanes aculeata Willd. (Arecaceae); structure in first source	2	1	0	stilbenoid
kaempferol-3-o-rutinoside kaempferol-3-O-rutinoside: isolated from the methanolic extract of the whole plants of Diodia teres through repeated silica gel and Sephadex LH-20 column chromatography; structure in first source. kaempferol-3-rutinoside : A kaempferol O-glucoside that is kaempferol attached to a rutinosyl [6-deoxy-alpha-L-mannosyl-(1->6)-beta-D-glucosyl] residue at position 3 via a glycosidic linkage. It has been isolated from the leaves of Solanum campaniforme.	2.49	2	0	disaccharide derivative; kaempferol O-glucoside; rutinoside; trihydroxyflavone	metabolite; plant metabolite; radical scavenger
icaritin icaritin: structure in first source	2.49	2	0
icariin [no description available]	2.8	3	0	flavonols; glycosyloxyflavone	antioxidant; bone density conservation agent; EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor; phytoestrogen
ligustilide ligustilide: found in Umbelliferae plants; RN given refers to cpd without isomeric designation; structure in first source	2.07	1	0	butenolide	metabolite
methyl brevifolincarboxylate methyl brevifolincarboxylate: isolated from Phyllanthus urinaria; structure in first source. methyl brevifolincarboxylate : An organic heterotricyclic compound that is 1,2,3,5-tetrahydrocyclopenta[c]isochromene substituted by hydroxy groups at positions 7, 8 and 9, oxo groups at positions 3 and 5 and a methoxycarbonyl group at position 1. Isolated from Phyllanthus urinaria and Phyllanthus niruri, it exhibits vasorelaxant activity.	2.17	1	0	cyclic ketone; delta-lactone; organic heterotricyclic compound; phenols	EC 5.99.1.2 (DNA topoisomerase) inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; metabolite; platelet aggregation inhibitor; radical scavenger; vasodilator agent
methyl-p-coumarate methyl-p-coumarate: structure in first source. 4-coumaric acid methyl ester : A cinnamate ester that is the methyl ester of 4-coumaric acid.	2.45	2	0	4-coumaric acid methyl ester
neoisoliquiritin neoisoliquiritin: inhibits angiogenesis; isolated from licorice root; isoliquiritin is the (E)-isomer; structure in first source; isoliquiritin is also available	2.08	1	0	flavonoids; glycoside
5,7-dihydroxy-6-methoxy-2-phenylchromen-4-one 5,7-dihydroxy-6-methoxy-2-phenylchromen-4-one: isolated from the Chinese herb Scutellariae radix. oroxylin A : A dihydroxy- and monomethoxy-flavone in which the hydroxy groups are positioned at C-5 and C-7 and the methoxy group is at C-6.	2.17	1	0	dihydroxyflavone; monomethoxyflavone	antineoplastic agent; EC 1.14.13.39 (nitric oxide synthase) inhibitor
tiliroside tiliroside: isolated from seeds of Eremocarpus setigerus	2.49	2	0	cinnamate ester; glycosyloxyflavone; monosaccharide derivative; trihydroxyflavone	plant metabolite
kaempferol-7-methyl ether rhamnocitrin : A monomethoxyflavone that is the 7-methyl ether derivative of kaempferol.	1.99	1	0	flavonols; monomethoxyflavone; trihydroxyflavone	plant metabolite
rhapontigenin rhapontigenin: structure in first source	2	1	0	stilbenoid
sophoricoside sophoricoside: from fruit of Sophora japonica; structure in first source	2.07	1	0	acrovestone; isoflavonoid
squamosamide squamosamide: natural compound from Annoma squamosa; FLZ is the synthetic cyclic analog; structure in first source	2.17	1	0
3',4',7-trihydroxyflavone 3',4',7-trihydroxyflavone: from the Sudanese medicinal plant Albizia zygia; structure in first source	2.54	2	0	flavones
casein kinase ii Casein Kinase II: A ubiquitous casein kinase that is comprised of two distinct catalytic subunits and dimeric regulatory subunit. Casein kinase II has been shown to phosphorylate a large number of substrates, many of which are proteins involved in the regulation of gene expression.	2.41	2	0
spd-304 SPD-304: structure in first source	2.11	1	0
semaxinib semaxanib : An oxindole that is 3-methyleneoxindole in which one of the hydrogens of the methylene group is replaced by a 3,5-dimethylpyrrol-2-yl group.	2.17	1	0	olefinic compound; oxindoles; pyrroles	angiogenesis modulating agent; antineoplastic agent; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor; vascular endothelial growth factor receptor antagonist
2'-hydroxy-4-methoxychalcone [no description available]	2.1	1	0
nifuroxazide nifuroxazide: structure	2.03	1	0	benzoic acids
ermanin ermanin: from Tanacetum microphyllum; structure given in first source. 3,4'-dimethylkaempferol : A dimethoxyflavone that is kaempferol in which the hydroxy groups at position 3 and 4' have been replaced by methoxy groups. It is a component of bee glue and isolated from several plant species including Tanacetum microphyllum.	2	1	0	dihydroxyflavone; dimethoxyflavone	anti-inflammatory agent; antimycobacterial drug; antineoplastic agent; apoptosis inducer; plant metabolite
guttiferone a guttiferone A: antibacterial from Clusiaceae family; structure in first source	2.05	1	0
lead Lead: A soft, grayish metal with poisonous salts; atomic number 82, atomic weight 207.2, symbol Pb.	4.63	8	0	carbon group element atom; elemental lead; metal atom	neurotoxin
12-hydroxy-5,8,10,14-eicosatetraenoic acid 12-Hydroxy-5,8,10,14-eicosatetraenoic Acid: A lipoxygenase metabolite of ARACHIDONIC ACID. It is a highly selective ligand used to label mu-opioid receptors in both membranes and tissue sections. The 12-S-HETE analog has been reported to augment tumor cell metastatic potential through activation of protein kinase C. (J Pharmacol Exp Ther 1995; 274(3):1545-51; J Natl Cancer Inst 1994; 86(15):1145-51)	2.4	2	0
15-hydroxy-5,8,11,13-eicosatetraenoic acid 15-hydroxy-5,8,11,13-eicosatetraenoic acid: potent & selective inhibitor of platelet lipoxygenase; RN given refers to cpd without isomeric designation	2.67	3	0
4-amylcinnamoylanthranilic acid 4-amylcinnamoylanthranilic acid: phospholipase A2 inhibitor. N-(p-amylcinnamoyl)anthranilic acid : An amidobenzoic acid that is anthranilic acid in which one of the anilino hydrogens is replaced by a 4-pentylcinnamoyl group. It is a transient receptor potential (TRP) channel blocker and phospholipase A2 (PLA2) inhibitor.	2	1	0	amidobenzoic acid; cinnamamides; secondary carboxamide	EC 3.1.1.4 (phospholipase A2) inhibitor; TRP channel blocker
(6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid (6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid : A dihydroxy monocarboxylic acid that is N-isopropylindole which is substituted at position 3 by a p-fluorophenyl group and at position 2 by a 6-carboxy-3,5-dihydroxyhex-1-en-1-yl group. It has four possible diastereoisomers.	2.1	1	0	dihydroxy monocarboxylic acid; indoles; organofluorine compound
5,5',6,6'-tetrachloro-1,1',3,3'-tetraethylbenzimidazolocarbocyanine 5,5',6,6'-tetrachloro-1,1',3,3'-tetraethylbenzimidazolocarbocyanine: structure given in first source. 1,1',3,3'-tetraethyl-5,5',6,6'-tetrachloroimidacarbocyanine : The cationic form of a C3 cyanine dye having 1,3-diethyl-5,6-dichloroindoleinine units at each end.	2.05	1	0	cyanine dye; indolium ion	fluorochrome
diamide Diamide: A sulfhydryl reagent which oxidizes sulfhydryl groups to the disulfide form. It is a radiation-sensitizing agent of anoxic bacterial and mammalian cells.	1.99	1	0	1,1'-azobis(N,N-dimethylformamide)
15-hydroxy-11 alpha,9 alpha-(epoxymethano)prosta-5,13-dienoic acid 15-Hydroxy-11 alpha,9 alpha-(epoxymethano)prosta-5,13-dienoic Acid: A stable prostaglandin endoperoxide analog which serves as a thromboxane mimetic. Its actions include mimicking the hydro-osmotic effect of VASOPRESSIN and activation of TYPE C PHOSPHOLIPASES. (From J Pharmacol Exp Ther 1983;224(1): 108-117; Biochem J 1984;222(1):103-110)	3.08	5	0
5,7-dihydroxy-4-methylcoumarin [no description available]	2.02	1	0	hydroxycoumarin
cesium Cesium: A member of the alkali metals. It has an atomic symbol Cs, atomic number 50, and atomic weight 132.91. Cesium has many industrial applications, including the construction of atomic clocks based on its atomic vibrational frequency.	2.25	1	0	alkali metal atom
barium Barium: An element of the alkaline earth group of metals. It has an atomic symbol Ba, atomic number 56, and atomic weight 138. All of its acid-soluble salts are poisonous.	2.87	4	0	alkaline earth metal atom; elemental barium
7,8-dihydroxy-4-methylcoumarin 7,8-dihydroxy-4-methylcoumarin: possess strong antioxidant and radical scavenging activities; structure in first source	2.02	1	0	hydroxycoumarin
rubidium Rubidium: An element that is an alkali metal. It has an atomic symbol Rb, atomic number 37, and atomic weight 85.47. It is used as a chemical reagent and in the manufacture of photoelectric cells.	2.91	4	0	alkali metal atom
codeine phosphate [no description available]	2.1	1	0
aluminum Aluminum: A metallic element that has the atomic number 13, atomic symbol Al, and atomic weight 26.98.	3.82	11	0	boron group element atom; elemental aluminium; metal atom
levorphanol Levorphanol: A narcotic analgesic that may be habit-forming. It is nearly as effective orally as by injection.	3.1	1	0	morphinane alkaloid
strontium Strontium: An element of the alkaline earth family of metals. It has the atomic symbol Sr, atomic number 38, and atomic weight 87.62.	1.96	1	0	alkaline earth metal atom
bismuth Bismuth: A metallic element that has the atomic symbol Bi, and atomic number 83. Its principal isotope is Bismuth 209.	8.6	28	2	metal atom; pnictogen
dihydromorphine Dihydromorphine: A semisynthetic analgesic used in the study of narcotic receptors.	2.1	1	0	morphinane alkaloid
arsenic Arsenic: A shiny gray element with atomic symbol As, atomic number 33, and atomic weight 75. It occurs throughout the universe, mostly in the form of metallic arsenides. Most forms are toxic. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), arsenic and certain arsenic compounds have been listed as known carcinogens. (From Merck Index, 11th ed)	2.9	3	0	metalloid atom; pnictogen	micronutrient
indium Indium: A metallic element, atomic number 49, atomic weight 114.818, symbol In. It is named from its blue line in the spectrum.. indium atom : A metallic element first identified and named from the brilliant indigo (Latin indicum) blue line in its flame spectrum.	1.94	1	0	boron group element atom
naltrexone Naltrexone: Derivative of noroxymorphone that is the N-cyclopropylmethyl congener of NALOXONE. It is a narcotic antagonist that is effective orally, longer lasting and more potent than naloxone, and has been proposed for the treatment of heroin addiction. The FDA has approved naltrexone for the treatment of alcohol dependence.. naltrexone : An organic heteropentacyclic compound that is naloxone substituted in which the allyl group attached to the nitrogen is replaced by a cyclopropylmethyl group. A mu-opioid receptor antagonist, it is used to treat alcohol dependence.	3.1	1	0	cyclopropanes; morphinane-like compound; organic heteropentacyclic compound	antidote to opioid poisoning; central nervous system depressant; environmental contaminant; mu-opioid receptor antagonist; xenobiotic
morphine-6-glucuronide morphine-6-glucuronide: RN given refers to (5alpha,6alpha)-isomer	2.1	1	0	morphinane alkaloid
gallium Gallium: A rare, metallic element designated by the symbol, Ga, atomic number 31, and atomic weight 69.72.. gallium atom : A metallic element predicted as eka-aluminium by Mendeleev in 1870 and discovered by Paul-Emile Lecoq de Boisbaudran in 1875. Named in honour of France (Latin Gallia) and perhaps also from the Latin gallus cock, a translation of Lecoq.	2.67	3	0	boron group element atom
butorphanol Butorphanol: A synthetic morphinan analgesic with narcotic antagonist action. It is used in the management of severe pain.. butorphanol : Levorphanol in which a hydrogen at position 14 of the morphinan skeleton is substituted by hydroxy and one of the hydrogens of the N-methyl group is substituted by cyclopropyl. A semi-synthetic opioid agonist-antagonist analgesic, it is used as its (S,S)-tartaric acid salt for relief or moderate to severe pain.	2.1	1	0	morphinane alkaloid	antitussive; kappa-opioid receptor agonist; mu-opioid receptor agonist; opioid analgesic
ramipril Ramipril: A long-acting angiotensin-converting enzyme inhibitor. It is a prodrug that is transformed in the liver to its active metabolite ramiprilat.. ramipril : A dipeptide that is the prodrug for ramiprilat, the active metabolite obtained by hydrolysis of the ethyl ester group. An angiotensin-converting enzyme (ACE) inhibitor, used to treat high blood pressure and congestive heart failure.. quark : Quarks comprise one of two classes of the fundamental particles. Quarks possess fractional electric charges and are not observed in free state. The word "quark" first appears in James Joyce's Finnegans Wake and has been chosen by Murray Gell-Mann as a name for fundamental building blocks of particles.	1.97	1	0	azabicycloalkane; cyclopentapyrrole; dicarboxylic acid monoester; dipeptide; ethyl ester	bradykinin receptor B2 agonist; cardioprotective agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; matrix metalloproteinase inhibitor; prodrug
sulfur Sulfur: An element that is a member of the chalcogen family. It has an atomic symbol S, atomic number 16, and atomic weight [32.059; 32.076]. It is found in the amino acids cysteine and methionine.	8	4	0	chalcogen; nonmetal atom	macronutrient
methyl oleate [no description available]	2.06	1	0	fatty acid methyl ester
costunolide [no description available]	2	1	0
n-(4-hydroxy-beta-phenethyl)-4-hydroxycinnamide trans-N-p-coumaroyl tyramine: from the twigs of Celtis chinensis; structure in first source	2.13	1	0	hydroxycinnamic acid	metabolite
plastoquinone [no description available]	2.51	2	0	plastoquinone
urolithin b urolithin B: has antiproliferative activity; structure in first source	2.54	2	0	coumarins
radicinin radicinin: mold metabolite from plant pathogen Stemphylium radicinum; RN given refers to (2S-(2alpha,3beta,7E))-isomer; structure	2.17	1	0	aromatic ketone
4,3',5'-tri-o-methylpiceatannol [no description available]	2	1	0
eleostearic acid eleostearic acid: RN given refers to cpd with unspecified isomeric designation	2.11	1	0	octadecatrienoic acid
3,3',4,5'-tetramethoxy-trans-stilbene (E)-3,4,3',5'-tetramethoxystilbene: from the leaves of Eugenia rigida; structure in first source	2	1	0
3,4',5-trimethoxystilbene 3,4',5-trimethoxystilbene: structure in first source	2	1	0
enalapril Enalapril: An angiotensin-converting enzyme inhibitor that is used to treat HYPERTENSION and HEART FAILURE.. enalapril : A dicarboxylic acid monoester that is ethyl 4-phenylbutanoate in which a hydrogen alpha to the carboxy group is substituted by the amino group of L-alanyl-L-proline (S-configuration).	2.1	1	0	dicarboxylic acid monoester; dipeptide	antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; geroprotector; prodrug
calycanthine calycanthine: the principal alkaloid of the plant family Calycanthaceae; RN given refers to (4bS)-(4balpha,5alpha,10balpha,11alpha)-isomer. calycanthine : The principal alkaloid of the plant family Calycanthaceae.	2.17	1	0	aminal; calycanthaceous alkaloid; organonitrogen heterocyclic compound
cytochalasin e cytochalasin E: structure	1.99	1	0	cytochalasan alkaloid	metabolite
dimyristoylphosphatidylcholine 1,2-di-O-myristoyl-sn-glycero-3-phosphocholine : A 1,2-diacyl-sn-glycero-3-phosphocholine where the two phosphatidyl acyl groups are specified as tetradecanoyl (myristoyl).. dimyristoyl phosphatidylcholine : A phosphatidylcholine where the phosphatidyl acyl groups are specified as tetradecanoyl (myristoyl).	2.54	2	0	1,2-diacyl-sn-glycero-3-phosphocholine; phosphatidylcholine 28:0; tetradecanoate ester	antigen; mouse metabolite
sedoheptulose [no description available]	2.03	1	0	ketoheptose
deoxyribose [no description available]	2.42	2	0	deoxypentose	human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
fumarates Fumarates: Compounds based on fumaric acid.. fumarate(2-) : A C4-dicarboxylate that is the E-isomer of but-2-enedioate(2-)	4.19	5	0	butenedioate; C4-dicarboxylate	human metabolite; metabolite; Saccharomyces cerevisiae metabolite
3-dehydroshikimate 3-dehydroshikimate : A monocarboxylic acid anion that is the conjugate base of 3-dehydroshikimic acid, arising from deprotonation of the carboxy group.. 3-dehydroshikimic acid : A 4-oxo monocarboxylic acid that is shikimic acid in which the allylic hydroxy group has been oxidised to the corresponding keto group.	2.93	4	0	monocarboxylic acid anion	Saccharomyces cerevisiae metabolite
beryllium Beryllium: An element with the atomic symbol Be, atomic number 4, and atomic weight 9.01218. Short exposure to this element can lead to a type of poisoning known as BERYLLIOSIS.. beryllium atom : Alkaline earth metal atom with atomic number 4.	7.03	1	0	alkaline earth metal atom; elemental beryllium; metal allergen	adjuvant; carcinogenic agent; epitope
bleomycin [no description available]	2.05	1	0	bleomycin	antineoplastic agent; metabolite
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	5.44	14	1	cysteinium	fundamental metabolite
silicon Silicon: A trace element that constitutes about 27.6% of the earth's crust in the form of SILICON DIOXIDE. It does not occur free in nature. Silicon has the atomic symbol Si, atomic number 14, and atomic weight [28.084; 28.086].	7.39	2	0	carbon group element atom; metalloid atom; nonmetal atom
boron Boron: A trace element with the atomic symbol B, atomic number 5, and atomic weight [10.806; 10.821]. Boron-10, an isotope of boron, is used as a neutron absorber in BORON NEUTRON CAPTURE THERAPY.	2.48	2	0	boron group element atom; metalloid atom; nonmetal atom	micronutrient
heroin Heroin: A narcotic analgesic that may be habit-forming. It is a controlled substance (opium derivative) listed in the U.S. Code of Federal Regulations, Title 21 Parts 329.1, 1308.11 (1987). Sale is forbidden in the United States by Federal statute. (Merck Index, 11th ed). heroin : A morphinane alkaloid that is morphine bearing two acetyl substituents on the O-3 and O-6 positions. As with other opioids, heroin is used as both an analgesic and a recreational drug. Frequent and regular administration is associated with tolerance and physical dependence, which may develop into addiction. Its use includes treatment for acute pain, such as in severe physical trauma, myocardial infarction, post-surgical pain, and chronic pain, including end-stage cancer and other terminal illnesses.	2.1	1	0	morphinane alkaloid	mu-opioid receptor agonist; opioid analgesic; prodrug
enalaprilat anhydrous Enalaprilat: The active metabolite of ENALAPRIL and one of the potent, intravenously administered, ANGIOTENSIN-CONVERTING ENZYME INHIBITORS. It is an effective agent for the treatment of essential hypertension and has beneficial hemodynamic effects in heart failure. The drug produces renal vasodilation with an increase in sodium excretion.. enalaprilat dihydrate : The dihydrate form of enalaprilat, an angiotensin-converting enzyme (ACE) inhibitor that is used (often in the form of its prodrug, enalapril) in the treatment of hypertension and heart failure, for reduction of proteinuria and renal disease in patients with nephropathies, and for the prevention of stroke, myocardial infarction, and cardiac death in high-risk patients. Unlike enalapril, enalaprilat is not absorbed by mouth but is administered by intravenous injection.. enalaprilat (anhydrous) : Enalapril in which the ethyl ester group has been hydrolysed to the corresponding carboxylic acid. Enalaprilat is an angiotensin-converting enzyme (ACE) inhibitor and is used (often in the form of its prodrug, enalapril) in the treatment of hypertension and heart failure, for reduction of proteinuria and renal disease in patients with nephropathies, and for the prevention of stroke, myocardial infarction, and cardiac death in high-risk patients. Unlike enalapril, enalaprilat is not absorbed by mouth but is given by intravenous injection, usually as the dihydrate.	2.44	2	0	dicarboxylic acid; dipeptide	antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor
normorphine normorphine: RN given refers to (5 alpha,6 alpha)-isomer	3.54	2	0	morphinane alkaloid
2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid 2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid: chromogen in glucose oxidase-peroxidase method for determining serum glucose; used in free radical scavenging assays; structure in first source	5	36	0
gamma-mangostin gamma-mangostin : A member of the class of xanthones that is 9H-xanthene substituted by hydroxy group at positions 1, 3, 6 and 7, an oxo group at position 9 and prenyl groups at positions 2 and 8. Isolated from the stems of Cratoxylum cochinchinense, it exhibits antitumour activity.	2.49	2	0	phenols; xanthones	antineoplastic agent; plant metabolite; protein kinase inhibitor
ramiprilat ramiprilat : A dipeptide that is the active metabolite of ramipril. An angiotensin-converting enzyme (ACE) inhibitor, used to treat high blood pressure and congestive heart failure.	1.97	1	0	azabicycloalkane; cyclopentapyrrole; dicarboxylic acid; dipeptide	bradykinin receptor B2 agonist; cardioprotective agent; drug metabolite; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; matrix metalloproteinase inhibitor
2,3-dehydrosilybin dehydrosilybin: inhibits cytochrome P450 1A1 catalytic activity; structure in first source	2.13	1	0	flavonolignan
panaxynol [no description available]	2.01	1	0	long-chain fatty alcohol
artepillin c artepillin C: RN refers to (E)-isomer	2.15	1	0
pepstatin pepstatin: inhibits the aspartic protease endothiapepsin	2.39	2	0	pentapeptide; secondary carboxamide	bacterial metabolite; EC 3.4.23.* (aspartic endopeptidase) inhibitor
pradimicin a pradimicin A: from actinomycete strain No. P157-2; has inhibitory effect against HIV in vitro; structure given in first source. pradimicin A : A member of the class of pradimicins that is isolated from the cultured broth of Actinomadura hibisca No. P157-2 (ATCC 53557).	2.11	1	0	aromatic ether; carboxylic acid; disaccharide derivative; L-alanine derivative; p-quinones; polyphenol; pradimicin; secondary alcohol
cefepime Cefepime: A fourth-generation cephalosporin antibacterial agent that is used in the treatment of infections, including those of the abdomen, urinary tract, respiratory tract, and skin. It is effective against PSEUDOMONAS AERUGINOSA and may also be used in the empiric treatment of FEBRILE NEUTROPENIA.. cefepime : A cephalosporin bearing (1-methylpyrrolidinium-1-yl)methyl and (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido groups at positions 3 and 7, respectively, of the cephem skeleton.	2.41	1	0	cephalosporin; oxime O-ether	antibacterial drug
guajavarin guajavarin: from leaves of Psidium guajava	2.76	3	0
narcissin flavonol narcissin flavonol: flavanol glycoside from Strumpfia maritima; do not confuse with other narcissin in Chemline, an alkaloid (lycorine (NM))	2.45	2	0	disaccharide derivative; glycosyloxyflavone; monomethoxyflavone; trihydroxyflavone
urolithin d urolithin D: has antiproliferative activity; structure in first source	2.21	1	0	hydroxycoumarin
xanthoepocin Xanthoepocin: an antibiotic from Penicillium simplicissimum IFO5762; structure in first source	2.17	1	0
pachymic acid pachymic acid: inhibits phospholipase A2; isolated from Poria cocos; structure in first source	2.13	1	0	triterpenoid
morphine-3-glucuronide morphine-3-glucuronide: RN given refers to (5alpha,6alpha)-isomer	2.1	1	0	morphinane alkaloid
lespenefril lespenefril: RN given refers to (L)-isomer. kaempferol 3,7-di-O-alpha-L-rhamnoside : A glycosyloxyflavone that is kaempferol attached to alpha-L-rhamnopyranosyl residues at positions 3 and 7 respectively via glycosidic linkages. It has been isolated from the aerial parts of Vicia faba and Lotus edulis.	2.05	1	0	alpha-L-rhamnoside; dihydroxyflavone; glycosyloxyflavone; monosaccharide derivative; polyphenol	anti-inflammatory agent; antidepressant; antineoplastic agent; apoptosis inducer; bone density conservation agent; hypoglycemic agent; immunomodulator; plant metabolite
sinigrin sinigrin: glucosinate in mustard seeds etc.; RN given refers to parent cpd. sinigrin : An alkenylglucosinolic acid that consists of 1-thio-beta-D-glucopyranose having a 4-[(sulfooxy)imino]but-1-en-4-yl group attached to the anomeric sulfur.	2.03	1	0	alkenylglucosinolic acid
naltrindole benzofuran naltrindole benzofuran: structure given in first source	3.1	1	0	morphinane alkaloid
myricetin 3-o-glucuronide myricetin 3-O-glucuronide: from Epilobium angustifolium. myricetin 3-O-glucuronide : A myricetin O-glucuronide that is myricetin with a beta-D-glucosiduronic acid residue attached at the 3-position.	2.15	1	0	monosaccharide derivative; myricetin O-glucuronide; pentahydroxyflavone	metabolite
quercetin 3-sambubioside quercetin 3-sambubioside: isolated from Actinidia arguta. quercetin 3-O-[beta-D-xylosyl-(1->2)-beta-D-glucoside] : A quercetin O-glucoside that is quercetin attached to a beta-D-sambubiosyl residue at position 3 via a glycosidc linkage.	2.44	2	0	disaccharide derivative; quercetin O-glucoside; tetrahydroxyflavone	antioxidant; plant metabolite
3,8-dihydroxy-6h-dibenzo(b,d)pyran-6-one 3,8-dihydroxy-6H-dibenzo(b,d)pyran-6-one: metabolite of ellagic acid	2.47	2	0	coumarins	geroprotector
3,3'-di-o-methylellagic acid 3,3'-di-O-methylellagic acid: structure given in first source	2.59	2	0
avicularin avicularin: from Polygonum aviculare L.; RN given refers to L-isomer. avicularin : A quercetin O-glycoside in which an alpha-L-arabinofuranosyl residue is attached at position 3 of quercetin via a glycosidic linkage. It is isolated particularly from Juglans regia and Foeniculum vulgare.	2.44	2	0	alpha-L-arabinofuranoside; monosaccharide derivative; quercetin O-glycoside; tetrahydroxyflavone	hepatoprotective agent; plant metabolite
hibifolin hibifolin: isolated from Helichrysum bracteatum; structure given in first source	2.06	1	0
beta-Mangostin [no description available]	2.11	1	0	xanthones
9-Hydroxycalabaxanthone [no description available]	2.11	1	0	xanthones
naltrindole naltrindole: delta opioid receptor antagonist	3.1	1	0	isoquinolines
carbocyanines Carbocyanines: Compounds that contain three methine groups. They are frequently used as cationic dyes used for differential staining of biological materials.	2.05	1	0	cyanine dye; organic iodide salt	fluorochrome
lyoniside daucosterol : A steroid saponin that is sitosterol attached to a beta-D-glucopyranosyl residue at position 3 via a glycosidic linkage. It has bee isolated from Panax japonicus var. major and Breynia fruticosa.	2.75	3	0	beta-D-glucoside; monosaccharide derivative; steroid saponin	plant metabolite
quercetin-3'-o-beta-d-glucopyranoside quercetin 3'-O-glucoside: structure in first source	2.58	2	0
cinidon-ethyl Lotus: A genus of the PEA FAMILY. The genus Lotus, formerly known as Tetragonolobus, is unrelated to other plants with the common name of lotus (NELUMBO and NYMPHAEA).. cinidon ethyl : A carboxylic ester and organochlorine compound that is the ethyl ester of cinidon.	2.25	1	0	ethyl ester; isoindoles; monochlorobenzenes	herbicide
1,2-dielaidoylphosphatidylethanolamine 1,2-dielaidoylphosphatidylethanolamine: RN given refers to (E,E)-isomer; member of a class of cationic lipid formulations called cytofectins	2.1	1	0
benzyl caffeate benzyl caffeate: isolated from Liaoxi propolis	2.21	1	0
6-(bromomethylene)tetrahydro-3-(1-naphthaleneyl)-2h-pyran-2-one 6-(bromomethylene)tetrahydro-3-(1-naphthaleneyl)-2H-pyran-2-one: structure given in first source; potent irreversible, mechanism-based inhibitor of myocardial calcium-independent phospholipase A2	2.01	1	0	naphthalenes
ammonium sulfate Ammonium Sulfate: Sulfuric acid diammonium salt. It is used in CHEMICAL FRACTIONATION of proteins.. ammonium sulfate : An inorganic sulfate salt obtained by reaction of sulfuric acid with two equivalents of ammonia. A high-melting (decomposes above 280degreeC) white solid which is very soluble in water (70.6 g/100 g water at 0degreeC; 103.8 g/100 g water at 100degreeC), it is widely used as a fertilizer for alkaline soils.	2.17	1	0	ammonium salt; inorganic sulfate salt	fertilizer
4,4'-diisothiocyanostilbene-2,2'-disulfonic acid 4,4'-Diisothiocyanostilbene-2,2'-Disulfonic Acid: An inhibitor of anion conductance including band 3-mediated anion transport.	3.23	6	0
3,5-dihydroxy-4'-methoxystilbene 4'-methoxyresveratrol: has anti-inflammatory effects in cell culture model	2	1	0
mastoparan [no description available]	1.99	1	0	mastoparans; peptidyl amide	antimicrobial agent
tetrodotoxin Tetrodotoxin: An aminoperhydroquinazoline poison found mainly in the liver and ovaries of fishes in the order TETRAODONTIFORMES, which are eaten. The toxin causes paresthesia and paralysis through interference with neuromuscular conduction.. tetrodotoxin : A quinazoline alkaloid that is a marine toxin isolated from fish such as puffer fish. It has been shown to exhibit potential neutotoxicity due to its ability to block voltage-gated sodium channels.	2.9	4	0	azatetracycloalkane; oxatetracycloalkane; quinazoline alkaloid	animal metabolite; bacterial metabolite; marine metabolite; neurotoxin; voltage-gated sodium channel blocker
quercetin-3-o-alpha-l-rhamnopyranoside quercetin-3-O-alpha-L-rhamnopyranoside: from Rhododendron ovatum Planch; structure in first source	2.74	3	0
germanium Germanium: A rare metal element with a blue-gray appearance and atomic symbol Ge, atomic number 32, and atomic weight 72.63.	2.17	1	0	carbon group element atom; metalloid atom; nonmetal atom
selenium Selenium: An element with the atomic symbol Se, atomic number 34, and atomic weight 78.97. It is an essential micronutrient for mammals and other animals but is toxic in large amounts. Selenium protects intracellular structures against oxidative damage. It is an essential component of GLUTATHIONE PEROXIDASE.	7.94	4	0	chalcogen; nonmetal atom	micronutrient
tellurium Tellurium: An element that is a member of the chalcogen family. It has the atomic symbol Te, atomic number 52, and atomic weight 127.60. It has been used as a coloring agent and in the manufacture of electrical equipment. Exposure may cause nausea, vomiting, and CNS depression.	7.82	2	0	chalcogen; metalloid atom
oxalates Oxalates: Derivatives of OXALIC ACID. Included under this heading are a broad variety of acid forms, salts, esters, and amides that are derived from the ethanedioic acid structure.	2.38	2	0
(-)-catechin-3-O-gallate (-)-catechin-3-O-gallate : A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of (-)-catechin.	3.68	2	0	flavans; gallate ester; polyphenol	metabolite
dizocilpine maleate Dizocilpine Maleate: A potent noncompetitive antagonist of the NMDA receptor (RECEPTORS, N-METHYL-D-ASPARTATE) used mainly as a research tool. The drug has been considered for the wide variety of neurodegenerative conditions or disorders in which NMDA receptors may play an important role. Its use has been primarily limited to animal and tissue experiments because of its psychotropic effects.. dizocilpine maleate : A maleate salt obtained by reaction of dizocilpine with one equivalent of maleic acid.	2.91	4	0	maleate salt; tetracyclic antidepressant	anaesthetic; anticonvulsant; neuroprotective agent; nicotinic antagonist; NMDA receptor antagonist
antimycin a Antimycin A: An antibiotic substance produced by Streptomyces species. It inhibits mitochondrial respiration and may deplete cellular levels of ATP. Antimycin A1 has been used as a fungicide, insecticide, and miticide. (From Merck Index, 12th ed). antimycin A : A nine-membered bis-lactone having methyl substituents at the 2- and 6-positions, an n-hexyl substituent at the 8-position, an acyloxy substituent at the 7-position and an aroylamido substituent at the 3-position. It is produced by Streptomyces bacteria and has found commercial use as a fish poison.	2.38	2	0	amidobenzoic acid
1-palmitoyl-2-oleoylphosphatidylcholine 1-palmitoyl-2-oleoylphosphatidylcholine: RN given refers to (Z)-isomer	2.53	2	0
falcarindiol falcarindiol: from leaves of Schefflera digitata (Araliaceae) and in carrots; inhibits germination of spores of most common dermatophyte fungi	2.01	1	0	organic molecular entity	metabolite
columbianadin columbianadin: furanocoumarin isolated from Peucedanum palustre; RN given refers to columbianadin, (S-(Z))-isomer. columbianadin : An alpha,beta-unsaturated carboxylic ester obtained by formal condensation of the carboxy group of angelic acid with the hydroxy group of 2-[(8S)-2-oxo-8,9-dihydro-2H-furo[2,3-h][1]benzopyran-8-yl]propan-2-ol.	2.07	1	0	alpha,beta-unsaturated carboxylic ester; furanocoumarin	anti-inflammatory agent; antineoplastic agent; apoptosis inducer; hepatoprotective agent; plant metabolite; rat metabolite
carboprostacyclin carboprostacyclin: potent stable prostacyclin analog which inhibits platelet aggretation; do not confuse with carboprost (15-methyl-PGF2alpha); RN given refers to (3aS-(2Z,3aalpha,4alpha(1E,R*),5beta,6aalpha))-isomer; structure given in first source	1.97	1	0	prostanoid
1-oleoyl-2-acetylglycerol [no description available]	3.22	6	0	1,2-diglyceride
12-o-tetradeca-2,4,6,8-tetranoylphorbol-13-acetate [no description available]	1.96	1	0
bis(1,3-dibutylbarbiturate)trimethine oxonol bis(1,3-dibutylbarbiturate)trimethine oxonol: fluorescent probe for membrane potentials	2.02	1	0
herboxidiene herboxidiene: structure in first source; isolated from Streptomyces chromofuscus; a potent and selective herbicide (e.g. inactive against wheat); up-regulates the gene expression of LDL receptor	2.17	1	0
2,3,5,4'-tetrahydroxystilbene 2-o-glucopyranoside 2,3,5,4'-tetrahydroxystilbene 2-O-glucopyranoside: isolated from dried root tubers of Polygonum multiflorum; structure in first source	2.52	2	0
aurachin c aurachin C: extracted from myxobacterium, Stigmatella aurantiaca strain Sg a15; MF: C25-H33-N-O2; MW: 379; structure given in first source. aurachin C : A C-type aurachin that is quinolin-4-one which is substituted by a hydroxy group at positions 1, a methyl group at position 2, and a triprenyl group at position 3.	1.98	1	0	C-type aurachin; hydroxylamines; organic heterobicyclic compound; quinolone	antibacterial agent; bacterial metabolite; EC 1.8.5.4 (sulfide:quinone reductase) inhibitor
caftaric acid [no description available]	2.88	3	0	hydroxycinnamic acid
plastoquinol plastoquinol: reduced form of plastoquinone. plastoquinol : A prenyl- or polyprenyl-hydroquinone that results from the reduction of a plastoquinone to the corresponding hydroquinone.. plastoquinol-9 : A plastoquinol in which an all-E nonaprenyl group is attached to position 5 of 2,3-dimethylhydroquinone.	2.1	1	0	plastoquinol
fukinolic acid fukinolic acid: also a carboxypeptidase A inhibitor; RN given for (S-(R,S))-isomer; structure in first source	2.03	1	0	hydroxycinnamic acid
perflubron demethylxanthohumol: an apoptosis-inducing agent from hops; structure in first source. desmethylxanthohumol : A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 4, 2', 4', and 6' and a 3-methylbut-2-en-1-yl group at position 3'.	2.15	1	0	2-acyl-4-prenylphloroglucinol; chalcones	plant metabolite
hydroxysafflor yellow a hydroxysafflor yellow A: from Carthamus tinctorius; structure given in first source. hydroxysafflor yellow A : A C-glycosyl compound that is 3,4,5-trihydroxycyclohexa-2,5-dien-1-one which is substituted by beta-D-glucosyl groups at positions 2 and 4, and by a p-hydroxycinnamoyl group at position 6. It is the main bioactive compound of a traditional Chinese medicine obtained from safflower (Carthamus tinctorius).	2.51	2	0
chlorophyll chlorophyll a': RN refers to (SP-4-2-(3S-(3alpha(2E,7S,11S),4beta,21alpha)))-isomer	2.1	1	0
pai 039 tiplaxtinin: inhibitor of plasminogen activator inhibitor-1	2.05	1	0	indole-3-acetic acids
salvianolic acid B salvianolic acid B: isolated from Salvia miltiorrhiza. salvianolic acid B : A member of the class of 1-benzofurans that is an antioxidant and free radical scavenging compound extracted from S. miltiorrhiza	2.13	1	0	1-benzofurans; catechols; dicarboxylic acid; enoate ester; polyphenol	anti-inflammatory agent; antidepressant; antineoplastic agent; antioxidant; apoptosis inducer; autophagy inhibitor; cardioprotective agent; hepatoprotective agent; hypoglycemic agent; neuroprotective agent; osteogenesis regulator; plant metabolite
i(3)so3-galactosylceramide Sulfoglycosphingolipids: GLYCOSPHINGOLIPIDS with a sulfate group esterified to one of the sugar groups.. 1-(3-O-sulfo-beta-D-galactosyl)-N-tetracosanoylsphingosine : A D-galactosyl-N-acylsphingosine having a sulfo group at the 3-position on the galactose ring and tetracosanoyl as the N-acyl group.	2.38	2	0	galactosylceramide sulfate; N-acyl-beta-D-galactosylsphingosine
alpha-cyperone alpha-cyperone: isolated from the rhizomes of Cyperus rotundus; structure in first source	2.07	1	0
19-hydroxycholesterol 19-hydroxycholesterol: structure given in first source	3.1	1	0	cholestanoid
2''-galloylhyperin 2''-galloylhyperin: isolated from Pyrola calliantha	3.33	6	0	flavonoids; glycoside
(1Ar,7aS,10aS,10bS)-1a,5-dimethyl-8-methylidene-2,3,6,7,7a,8,10a,10b-octahydrooxireno[9,10]cyclodeca[1,2-b]furan-9(1aH)-one [no description available]	2.17	1	0	germacranolide
methyl chlorogenate methyl chlorogenate: from Eriobotrya japonica; structure in first source	2.13	1	0	quinic acid
isoacteoside isoacteoside: a phenylethanoid glycoside isolated from Indian paintbrush (Verbenaceae) Castilleja linariaefolia; also in other plants; structure given in first source	2.01	1	0	hydroxycinnamic acid
panduratin a panduratin A: isolated from Kaempferia pandurata; structure in first source	2.54	2	0	diarylheptanoid	metabolite
rosaramicin rosaramicin: RN given refers to parent cpd. rosaramicin : A macrolide antibiotic with activity against Neisseria gonorrhoeae, Chlamydia trachomatis, Ureaplasma urealyticum and Mycoplasma hominis.	2.1	1	0	aldehyde; enone; epoxide; macrolide antibiotic; monosaccharide derivative	bacterial metabolite
beta-escin [no description available]	5.24	11	1
borneol [no description available]	3.1	1	0	borneol
emetine hydrochloride [no description available]	2.01	1	0
s-nitroso-n-acetylpenicillamine S-Nitroso-N-Acetylpenicillamine: A sulfur-containing alkyl thionitrite that is one of the NITRIC OXIDE DONORS.	1.99	1	0	nitroso compound; nitrosothio compound	nitric oxide donor; vasodilator agent
nifurtimox Nifurtimox: A nitrofuran thiazine that has been used against TRYPANOSOMIASIS.	2.13	1	0	nitrofuran antibiotic
shellac shellac: RN given refers to parent cpd	2.1	1	0
morphinans Morphinans: Compounds based on a partially saturated iminoethanophenanthrene, which can be described as ethylimino-bridged benzo-decahydronaphthalenes. They include some of the OPIOIDS found in PAPAVER that are used as ANALGESICS.	1.95	1	0	isoquinoline alkaloid fundamental parent; morphinane alkaloid
ergoline Ergolines: A series of structurally-related alkaloids that contain the ergoline backbone structure.. ergoline : An indole alkaloid whose structural skeleton is found in many naturally occurring and synthetic ergolines which are known to bind to neurotransmitter receptors, such as dopamine, noradrenaline and serotonin receptors and function as unselective agonists or antagonists at these receptors.	1.98	1	0	diamine; ergoline alkaloid; indole alkaloid fundamental parent; indole alkaloid; organic heterotetracyclic compound
adenosine-3',5'-cyclic phosphorothioate adenosine-3',5'-cyclic phosphorothioate: RP-cAMP-S is a protein kinase A inhibitor; SP-cAMP-S is a protein kinase A agonist. (Sp)-cAMPS : A nucleoside 3',5'-cyclic phosphorothioate having adenine as the nucleobase (the Sp-stereoisomer).. (Rp)-cAMPS : A nucleoside 3',5'-cyclic phosphorothioate having adenine as the nucleobase (the Rp-stereoisomer).	2	1	0	nucleoside 3',5'-cyclic phosphorothioate
sq-23377 Ionomycin: A divalent calcium ionophore that is widely used as a tool to investigate the role of intracellular calcium in cellular processes.. ionomycin : A very long-chain fatty acid that is docosa-10,16-dienoic acid which is substituted by methyl groups at positions 4, 6, 8, 12, 14, 18 and 20, by hydroxy groups at positions 11, 19 and 21, and by a (2',5-dimethyloctahydro-2,2'-bifuran-5-yl)ethanol group at position 21. An ionophore produced by Streptomyces conglobatus, it is used in research to raise the intracellular level of Ca(2+) and as a research tool to understand Ca(2+) transport across biological membranes.	4.47	23	0	cyclic ether; enol; polyunsaturated fatty acid; very long-chain fatty acid	calcium ionophore; metabolite
roxithromycin (E)-roxithromycin : A major geometrical isomer of roxithromycin.	2.1	1	0	roxithromycin	environmental contaminant; xenobiotic
cefdinir [no description available]	2.1	1	0	cephalosporin; ketoxime	antibacterial drug
(3S,6S,9S,12R)-3-[(2S)-Butan-2-yl]-6-[(1-methoxyindol-3-yl)methyl]-9-(6-oxooctyl)-1,4,7,10-tetrazabicyclo[10.4.0]hexadecane-2,5,8,11-tetrone [no description available]	2.17	1	0	oligopeptide
beta-elemene beta-elemene: increases tumor cell immunogenicity by inducing, at least in part, elevated expression of heat shock protein 70 on tumor cell surface. beta-elemene : A sesquiterpene that consists of cyclohexane bearing methyl and vinyl substituents at position 1 as well as two isopropenyl substituents at positions 2 and 4.. (-)-beta-elemene : The (-)-enantiomer of beta-elemene that has (1S,2S,4R)-configuration.	2.21	1	0	beta-elemene	antineoplastic agent
vildagliptin [no description available]	3.27	1	0	amino acid amide
corosolic acid [no description available]	2.1	1	0	triterpenoid	metabolite
panobinostat Panobinostat: An indole and hydroxamic acid derivative that acts as a HISTONE DEACETYLASE inhibitor. It is used as an antineoplastic agent in combination with BORTEZOMIB and DEXAMETHASONE for the treatment of MULTIPLE MYELOMA.. panobinostat : A hydroxamic acid obtained by formal condensation of the carboxy group of (2E)-3-[4-({[2-(2-methylindol-3-yl)ethyl]amino}methyl)phenyl]prop-2-enoic acid with the amino group of hydroxylamine. A histone deacetylase inhibitor used (as its lactate salt) in combination with bortezomib and dexamethasone for the treatment of multiple myeloma.	7.17	1	0	cinnamamides; hydroxamic acid; methylindole; secondary amino compound	angiogenesis modulating agent; antineoplastic agent; EC 3.5.1.98 (histone deacetylase) inhibitor
rebaudioside a rebaudioside A: glucoside isolated from the leaves of the paraguayan shrub, Stevia rebaudiana; has taste properties superior to stevioside; structure in first source. rebaudioside A : A rebaudioside that is rubusoside in which the hydroxy groups at positions 3 and 4 of the beta-D-glucopyranosyloxy group at the 13alpha position have both been converted to the corresponding beta-D-glucopyranoside.	2.41	1	0	beta-D-glucoside; rebaudioside; tetracyclic diterpenoid	sweetening agent
isoborneol isoborneol: RN given refers to cpd without isomeric designation; structure	2.01	1	0	borneol
phenylalanylphenylalanine Phe-Phe : A dipeptide formed from two L-phenylalanine residues.	2.1	1	0	dipeptide; L-aminoacyl-L-amino acid zwitterion	human blood serum metabolite; Mycoplasma genitalium metabolite
staurosporine staurosporinium : Conjugate acid of staurosporine.	4.24	18	0	ammonium ion derivative
13-epi-sclareol 13-epi-sclareol: an unusual labdane diterpene from the roots of Coleus forskohlii with cell growth inhibitory action in breast and uterine cancers in vitro; structure in first source	2.17	1	0
formazans Formazans: Colored azo compounds formed by the reduction of tetrazolium salts. Employing this reaction, oxidoreductase activity can be determined quantitatively in tissue sections by allowing the enzymes to act on their specific substrates in the presence of tetrazolium salts.	7.53	2	0
ferrihydrite ferric oxyhydroxide: an antiferromagnetic material; constitutes the core of natural ferritin; mol form 5Fe2O3.9H2O	7.31	1	0
s-allylcysteine S-allylcysteine: structure in first source; RN given refers to (L)-isomer. S-allylcysteine : An S-hydrocarbyl-L-cysteine that is L-cysteine in which the hydrogen attached to the sulphur is replaced by a prop-2-enyl group. It commonly occurs in garlic and has been found to exhibit antineoplastic activity.	2.21	1	0	L-alpha-amino acid zwitterion; S-hydrocarbyl-L-cysteine	antineoplastic agent; metabolite
bimosiamose bimosiamose: a selectin inhibitor	2.03	1	0
midostaurin midostaurin : An organic heterooctacyclic compound that is the N-benzoyl derivative of staurosporine.	1.99	1	0	benzamides; gamma-lactam; indolocarbazole; organic heterooctacyclic compound	antineoplastic agent; EC 2.7.11.13 (protein kinase C) inhibitor
dmp 728 DMP 728: structure in first source; RN given refers to the monomethane sulfate	1.99	1	0
sincalide Sincalide: An octapeptide hormone present in the intestine and brain. When secreted from the gastric mucosa, it stimulates the release of bile from the gallbladder and digestive enzymes from the pancreas.	3.08	5	0	oligopeptide
vasopressin, 1-(1-mercaptocyclohexaneacetic acid)-2-(o- methyl-l-tyrosine)-8-l-arginine- vasopressin, 1-(1-mercaptocyclohexaneacetic acid)-2-(O- methyl-L-tyrosine)-8-L-arginine-: highly potent antagonist of vasopressor response to arginine-vasopressin; structure in first source	1.97	1	0
fructosyl-lysine fructosyllysine : A glyco-amino acid consisting of a D-fructosyl residue attached to the epsilon-amino group of L-lysine.	2.21	1	0	fructosamine; glyco-amino acid	Escherichia coli metabolite
n(6)-cyclohexyladenosine N(6)-cyclohexyladenosine: structure given in first source; receptors, purinergic P1 agonist	1.97	1	0
gentamicin sulfate [no description available]	2.02	1	0
pinellic acid pinellic acid: structure in first source. pinellic acid : A trihydroxyoctadecenoic acid with hydroxy groups at positions C-9, -12, and 13, and an E (cis) double bond at position 10.	2.11	1	0	TriHOME	adjuvant; anti-inflammatory agent
mocetinostat mocetinostat: undergoing phase II clinical trials for treatment of cancer. mocetinostat : A benzamide obtained by formal condensation of the carboxy group of 4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzoic acid with one of the amino groups of benzene-1,2-diamine. It is an orally active and isotype-selective HDAC inhibitor which exhibits antitumour activity (IC50 = 0.15, 0.29, 1.66 and 0.59 muM for HDAC1, HDAC2, HDAC3 and HDAC11).	4.53	23	0	aminopyrimidine; benzamides; pyridines; secondary amino compound; secondary carboxamide; substituted aniline	antineoplastic agent; apoptosis inducer; autophagy inducer; cardioprotective agent; EC 3.5.1.98 (histone deacetylase) inhibitor; hepatotoxic agent
proanthocyanidin a1 procyanidin A1: from aqueous extract of peanut skin; structure in first source	2.11	1	0	flavonoid oligomer
lipid a Lipid A: Lipid A is the biologically active component of lipopolysaccharides. It shows strong endotoxic activity and exhibits immunogenic properties.. lipid A : The glycolipid moiety of bacterial lipopolysaccharide (R can be either hydrogen or a fatty acyl group).	2.39	2	0	dodecanoate ester; lipid A; tetradecanoate ester	Escherichia coli metabolite
mart-1 antigen MART-1 Antigen: A melanosome-specific protein that plays a role in the expression, stability, trafficking, and processing of GP100 MELANOMA ANTIGEN, which is critical to the formation of Stage II MELANOSOMES. The protein is used as an antigen marker for MELANOMA cells.	2.01	1	0
ginsenoside rb1 [no description available]	2.49	2	0	ginsenoside; glycoside; tetracyclic triterpenoid	anti-inflammatory drug; anti-obesity agent; apoptosis inhibitor; neuroprotective agent; plant metabolite; radical scavenger
ginsenoside rg3 ginsenoside Rg3: from Red ginseng; inhibits lung metastasis of tumor cells; structure given in first source. (20S)-ginsenoside Rg3 : A ginsenoside found in Panax ginseng and Panax japonicus var. major that is dammarane which is substituted by hydroxy groups at the 3beta, 12beta and 20 pro-S positions, in which the hydroxy group at position 3 has been converted to the corresponding beta-D-glucopyranosyl-beta-D-glucopyranoside, and in which a double bond has been introduced at the 24-25 position.	2.03	1	0	ginsenoside; glycoside; tetracyclic triterpenoid	angiogenesis modulating agent; antineoplastic agent; apoptosis inducer; plant metabolite
sorbitan monooleate [no description available]	2	1	0	fatty acid ester
norcodeine norcodeine: RN given refers to (5 alpha,6 alpha)-isomer. norcodeine : A morphinane-like compound that is the N-demethylated derivative of codeine.	3.54	2	0	morphinane alkaloid
glutinol glutinol: from a medicinal lichen, Usnea longissima; structure in first source. glutinol : A pentacyclic triterpenoid that is picene which has been fully hydrogenated except for a double bond between the 4a and 5 positions and is substituted by methyl groups at the 4, 4, 6bbeta, 8abeta, 11, 11, 12balpha and 14bbeta positions, and by a hydroxy group at the 3beta position.	2.04	1	0	pentacyclic triterpenoid; secondary alcohol
zeolites [no description available]	2.31	1	0
4-n-butyl-1-(4-(2-methylphenyl)-4-oxo-1-butyl)-piperidine hydrogen chloride [no description available]	2.1	1	0
g(m1) ganglioside G(M1) Ganglioside: A specific monosialoganglioside that accumulates abnormally within the nervous system due to a deficiency of GM1-b-galactosidase, resulting in GM1 gangliosidosis.. ganglioside GM1 : A sialotetraosylceramide consisting of a branched pentasaccharide made up from one sialyl residue, two galactose residues, one N-acetylgalactosamine residue and a glucose residue at the reducing end attached to N-stearoylsphingosine via a beta-linkage.	2.03	1	0	alpha-N-acetylneuraminosyl-(2->3)-[beta-D-galactosyl-(1->3)-N-acetyl-beta-D-galactosaminyl-(1->4)]-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1')-N-acylsphingosine; sialotetraosylceramide
4-hydroxyestrone 4-hydroxyestrone : A 4-hydroxy steroid that is estrone substituted by a hydroxy group at position 4.	3.1	1	0	17-oxo steroid; 3-hydroxy steroid; 4-hydroxy steroid; catechols; phenolic steroid	carcinogenic agent; estrogen; human urinary metabolite
aluminum oxide Aluminum Oxide: An oxide of aluminum, occurring in nature as various minerals such as bauxite, corundum, etc. It is used as an adsorbent, desiccating agent, and catalyst, and in the manufacture of dental cements and refractories.	8.03	4	0
linagliptin Linagliptin: A purine and quinazoline derivative that functions as an INCRETIN and DIPEPTIDYL-PEPTIDASE IV INHIBTOR. It is used as a HYPOGLYCEMIC AGENT in the treatment of TYPE II DIABETES MELLITUS.. linagliptin : A xanthine that is 7H-xanthine bearing (4-methylquinazolin-2-yl)methyl, methyl, but-2-yn-1-yl and 3-aminopiperidin-1-yl substituents at positions 1, 3, 7 and 8 respectively (the R-enantiomer). Used for treatment of type II diabetes.	8.69	2	0	aminopiperidine; quinazolines	EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; hypoglycemic agent
bismuth tripotassium dicitrate bismuth tripotassium dicitrate: contains tripotassium di-citratobismuthate used in gastric & duodenal ulcer therapy; do not confuse with colloidal bismuth subnitrate	2.38	2	0
huprine y huprine Y: structure in first source	2.1	1	0
decanoylcarnitine decanoylcarnitine: therapeutic agent for diabetic acidosis; RN given refers to cpd without isomeric designation. O-decanoylcarnitine : An O-acylcarnitine compound having decanoyl as the acyl substituent.	2.1	1	0	decanoate ester; O-acylcarnitine	human urinary metabolite
11 beta-hydroxyandrosterone 11 beta-hydroxyandrosterone: RN given refers to (3alpha,5alpha,11beta)-isomer; structure	3.1	1	0	3-hydroxy steroid	androgen
alpha-synuclein alpha-Synuclein: A synuclein that is a major component of LEWY BODIES and plays a role in SYNUCLEINOPATHIES, neurodegeneration and neuroprotection.	2.55	2	0
akuammicine akuammicine: from Strychnos sp;; structure in first source. akuammicine : A monoterpenoid indole alkaloid with formula C20H22N2O2, isolated from several plant species including Alstonia spatulata, Catharanthus roseus and Vinca major.	2.17	1	0	methyl ester; monoterpenoid indole alkaloid; organic heteropentacyclic compound; tertiary amino compound	plant metabolite
2-hydroxyestriol 2-hydroxyestriol: structure	3.1	1	0
glucosyringic acid [no description available]	2.47	2	0
hermitamide b hermitamide B: isolated from Lyngbya majuscula; structure in first source	2.17	1	0
macelignan macelignan: an NSAID with antioxidant, free radical scavenging, and neuroprotective activities; structure in first source	2.11	1	0	lignan
1-(hexylthio)-2-(hexanoylamino)-1,2-dideoxy-sn-glycero-3-phosphocholine 1-(hexylthio)-2-(hexanoylamino)-1,2-dideoxy-sn-glycero-3-phosphocholine: structure given in first source; an inhibitor of cobra venom phospholipase A2	2.01	1	0
furosin furosin: an ellagitannin from extract of leaves & stems of Phyllanthus sellowianus; structure given in first source	2	1	0
trans-delta-tocotrienoloic acid tocotrienoloic acid: from leaves of Tovomitopsis psychotriifolia; structure given in first source	2.17	1	0	tocotrienol
oxadiazoles Oxadiazoles: Compounds containing five-membered heteroaromatic rings containing two carbons, two nitrogens, and one oxygen atom which exist in various regioisomeric forms.	2.45	2	0
2,3-bis(3'-hydroxybenzyl)butyrolactone, (trans)-isomer [no description available]	2.03	1	0
nodulisporic acid a nodulisporic acid A: a novel indole diterpene insecticide; structure in first source	2.17	1	0
ucn 1028 c calphostin C: structure given in first source; isolated from Cladosporium cladosporioides	3.39	7	0
methyl cholate methyl cholate: RN given refers to (3 alpha,5 beta,7 alpha,12 alpha)-isomer	2.11	1	0	bile acid
ribose ribopyranose : The pyranose form of ribose.	2.69	2	0	D-ribose; ribopyranose
acebutolol alpha-D-glucosyl-(1->4)-alpha-D-mannose : An alpha-D-glucosyl-(1->4)-D-mannopyranose in which the anomeric hydroxy group has alpha configuration.	2.21	1	0	alpha-D-glucosyl-(1->4)-D-mannopyranose
Diosmetin 7-O-beta-D-glucopyranoside [no description available]	2.11	1	0	flavonoids; glycoside
idopyranose L-idose : The L-stereoisomer of idose.. L-idopyranose : The pyranose form of L-idose.	2.25	1	0	L-idose
palytoxin palytoxin: coelenterate toxin; composed of substituted N-3-hydroxypropyl-trans-3-amidoacrylamides. palytoxin : A polyol marine coelenterate toxin composed of substituted N-3-hydroxypropyl-trans-3-amidoacrylamides and produced by species of Palythoa and Zoanthus soft corals (collectively called zoantharians), either as a defence mechanism or to assist them in capturing prey. An ionophore that forms cation channels through Na+/K+-ATPase, it is a potent vasoconstrictor useful in evaluation of anti-angina agents. It is considered to be one of the most poisonous non-protein substances known, second only to maitotoxin in terms of toxicity in mice.	1.96	1	0	polyol	toxin
procyanidin b1 procyanidin B1 : A proanthocyanidin consisting of (-)-epicatechin and (+)-catechin units joined by a bond between positions 4 and 8' respectively in a beta-configuration.. Procyanidin B1 can be found in Cinnamomum verum (Ceylon cinnamon, in the rind, bark or cortex), in Uncaria guianensis (cat's claw, in the root), and in Vitis vinifera (common grape vine, in the leaf) or in peach.	2.46	2	0	biflavonoid; hydroxyflavan; polyphenol; proanthocyanidin	anti-inflammatory agent; EC 3.4.21.5 (thrombin) inhibitor; metabolite
nystatin a1 Nystatin: Macrolide antifungal antibiotic complex produced by Streptomyces noursei, S. aureus, and other Streptomyces species. The biologically active components of the complex are nystatin A1, A2, and A3.. nystatin : A heterogeneous mixture of polyene compounds produced by cultures of Streptomyces noursei. It mainly consists of three biologically active components designated nystatin A1, nystatin A2, and nystatin A3. It is used to treat oral and dermal fungal infections.. nystatin A1 : A polyene macrolide antibiotic; part of the nystatin complex produced by several Streptomyces species. It is an antifungal antibiotic used for the treatment of topical fungal infections caused by a broad spectrum of fungal pathogens comprising yeast-like and filamentous species.	2.47	2	0	nystatins
pirarubicin [no description available]	7.31	1	0	anthracycline
ks370g KS370G: antihyperglycemic; structure in first source	2.21	1	0
alogliptin alogliptin: structure in first source. alogliptin : A piperidine that is 3-methyl-2,4-dioxo-3,4-dihydropyrimidine carrying additional 2-cyanobenzyl and 3-aminopiperidin-1-yl groups at positions 1 and 2 respectively (the R-enantiomer). Used in the form of its benzoate salt for treatment of type 2 diabetes.	3.27	1	0	nitrile; piperidines; primary amino compound; pyrimidines	EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; hypoglycemic agent
gosogliptin [no description available]	3.27	1	0	amino acid amide
ro 31-8425 Ro 31-8425: structure given in first source	2.11	1	0
veratridine Veratridine: A benzoate-cevane found in VERATRUM and Schoenocaulon. It activates SODIUM CHANNELS to stay open longer than normal.	1.97	1	0
2,4,3',5'-tetrahydroxystilbene oleocanthal: newly pressed extra-virgin olive oil contains oleocanthal, acting as a natural anti-inflammatory compound that has a potency and profile strikingly similar to that of ibuprofen; structure in first source. oleocanthal : A carboxylic ester that is the 2-(p-hydroxyphenyl)ethyl ester of (3S)-4-formyl-3-(2-oxoethyl)hex-4-enoic acid. Oleocanthal is found in olive oil but it is not clear whether the natural product is a mixture of E/Z isomers or a single isomer as the two isomers readily interconvert in solution; most pharmacological studies will have been performed using a mixture.	2.03	1	0
lyoniresinol lyoniresinol: isoalted from the vine stem of Bauhinia championii; structure in first source. (+)-lyoniresinol : A lignan that is tetralin substituted by a 4-hydroxy-3,5-dimethoxy group at position 4, hydroxymethyl groups at positions 2 and 3, methoxy groups at positions 5 and 7 and a hydroxy group at position 6. Isolated from Machilus robusta and Sinocalamus affinis, it exhibits antineoplastic activity.	2.02	1	0	dimethoxybenzene; lignan; polyphenol; primary alcohol; tetralins	antineoplastic agent; metabolite
scopadulcic acid b scopadulcic acid B: isolated from Scorparia dulcis	2.17	1	0
gliocladin c gliocladin C: structure in first source	2.17	1	0
losartan potassium Erythropoietin: Glycoprotein hormone, secreted chiefly by the KIDNEY in the adult and the LIVER in the FETUS, that acts on erythroid stem cells of the BONE MARROW to stimulate proliferation and differentiation.	2.4	2	0
zincophorin zincophorin: 25 carbon polypropionate from Streptomyces griseus; griseochelin and M 144255 are the same monocarboxylic acid ionophore	2.17	1	0	pyrans	bacterial metabolite; ionophore
streptazolin streptazolin: from culture of Streptomyces sp.; structure in first source	2.17	1	0
chatancin chatancin: structure in first source	2.17	1	0
teneligliptin [no description available]	3.27	1	0	amino acid amide
palmitoylcarnitine Palmitoylcarnitine: A long-chain fatty acid ester of carnitine which facilitates the transfer of long-chain fatty acids from cytoplasm into mitochondria during the oxidation of fatty acids.. O-palmitoyl-L-carnitine : An O-acyl-L-carnitine in which the acyl group is specified as palmitoyl (hexadecanoyl).	1.97	1	0	O-palmitoylcarnitine; saturated fatty acyl-L-carnitine	EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; human metabolite; mouse metabolite
calcimycin Calcimycin: An ionophorous, polyether antibiotic from Streptomyces chartreusensis. It binds and transports CALCIUM and other divalent cations across membranes and uncouples oxidative phosphorylation while inhibiting ATPase of rat liver mitochondria. The substance is used mostly as a biochemical tool to study the role of divalent cations in various biological systems.	6.9	91	0	benzoxazole
dextrothyroxine [no description available]	2.41	1	0
sepharose agarose : A linear polysaccharide made up from alternating D-galactose and 3,6-anhydro-alpha-L-galactopyranose residues joined by alpha-(1->3)- and beta-(1->4)-linkages.	2.61	2	0
indocyanine green Indocyanine Green: A tricarbocyanine dye that is used diagnostically in liver function tests and to determine blood volume and cardiac output.	2.52	2	0	1,1-diunsubstituted alkanesulfonate; benzoindole; cyanine dye
copper oxychloride [no description available]	2.6	1	0
pituitrin Pituitrin: A substance or extract from the neurohypophysis (PITUITARY GLAND, POSTERIOR).	3.67	10	0
verproside verproside: from Pseudolysimachion longifolium; structure in first source	2.49	2	0	glycoside	metabolite
minecoside [no description available]	2.49	2	0	hydroxycinnamic acid	metabolite
morelloflavone morelloflavone: also inhibits cruzain; RN given for (2S-trans)-isomer; structure in first source. (+)-morelloflavone : A biflavonoid found in Rheedia edulis and Garcinia livingstonei.	2.17	1	0	biflavonoid; hydroxyflavanone; hydroxyflavone	plant metabolite
leojaponin leojaponin: from Leonurus japonicus leaves; structure in first source	2.15	1	0
cinnamosmolide cinnamosmolide: isolated from several species of Canellaceae family; structure in first source	2.17	1	0
phytosterols Phytosterols: A class of organic compounds known as sterols or STEROIDS derived from plants.. phytosterols : Sterols similar to cholesterol which occur in plants and vary only in carbon side chains and/or presence or absence of a double bond.	3.01	4	0
myricetin-3-o-galactoside myricetin-3-O-galactoside: antioxidant and antigenotoxic from Myrtus communis; structure in first source	2.15	1	0
clove Madagascar: One of the Indian Ocean Islands off the southeast coast of Africa. Its capital is Antananarivo. It was formerly called the Malagasy Republic. Discovered by the Portuguese in 1500, its history has been tied predominantly to the French, becoming a French protectorate in 1882, a French colony in 1896, and a territory within the French union in 1946. The Malagasy Republic was established in the French Community in 1958 but it achieved independence in 1960. Its name was changed to Madagascar in 1975. (From Webster's New Geographical Dictionary, 1988, p714)	3.64	8	0
helicide helicide: structure given in first source	2.02	1	0	glycoside
erythrosine Erythrosine: A tetraiodofluorescein used as a red coloring in some foods (cherries, fish), as a disclosure of DENTAL PLAQUE, and as a stain of some cell types. It has structural similarity to THYROXINE.. erythrosin B : An organic sodium salt that is the disodium salt of 2-(2,4,5,7-tetraiodo-6-oxido-3-oxo-8a,10a-dihydroxanthen-9-yl)benzoic acid.	1.98	1	0
mefloquine Mefloquine: A phospholipid-interacting antimalarial drug (ANTIMALARIALS). It is very effective against PLASMODIUM FALCIPARUM with very few side effects.. mefloquine : A racemate composed of (+)-(11R,2'S)- and (-)-(11S,2'R)-enantiomers of mefloquine. An antimalarial agent which acts as a blood schizonticide; its mechanism of action is unknown.	2.17	1	0
Shanzhiside methyl ester [no description available]	2.11	1	0	glycoside; iridoid monoterpenoid
cleomiscosin d cleomiscosin D: from the root bark of Hibiscus syriacus (Malvaceae); structure in first source	2.13	1	0
prim-o-glucosylcimifugin prim-O-glucosylcimifugin: from Peucedanum dissolutum; structure in first source	2.49	2	0	organic heterotricyclic compound; oxacycle
15-deoxygoyazensolide 15-deoxygoyazensolide: an NSAID with schistossomicidal and trypanosomicidal activities; structure in first source	2.17	1	0
lyoniside lyoniside: see also eleutherosides & syringin for eleutheroside B: 118-34-3; RN given refers to (3beta)-isomer	3.92	12	0
icatibant icatibant: a potent bradykinin (B2) receptor antagonist; WIN 65365 is an L-Tic(7) stereoisomer. icatibant : A ten-membered synthetic oligopeptide consisting of D-Arg, Arg, Pro, Hyp, Gly, Thi, Ser, D-Tic, Oic, and Arg residues joined in sequrence. A bradykinin receptor antagonist used as its acetate salt for the treatment of acute attacks of hereditary angioedema in adult patients.	2	1	0
mitragynine speciogynine: structure in first source	2.17	1	0
cyanidin-3-o-beta-glucopyranoside cyanidin-3-O-beta-glucopyranoside: a natural compound distributed in several fruits & vegetables, such as strawberry, rhubarb, cherry, red cabbage, red onion, cranberries, etc.	3.37	6	0
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	4.46	7	0	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
trelagliptin trelagliptin: a dipeptidyl peptidase IV inhibitor	3.27	1	0	benzenes; nitrile
cytochrome c-t Cytochromes c: Cytochromes of the c type that are found in eukaryotic MITOCHONDRIA. They serve as redox intermediates that accept electrons from MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX III and transfer them to MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX IV.	3.85	11	0
jaboticabin jaboticabin: depside from the fruit of jaboticaba (Myrciaria cauliflora); structure in first source	2.07	1	0
melitten Melitten: Basic polypeptide from the venom of the honey bee (Apis mellifera). It contains 26 amino acids, has cytolytic properties, causes contracture of muscle, releases histamine, and disrupts surface tension, probably due to lysis of cell and mitochondrial membranes.	4.59	8	0
cholecystokinin Cholecystokinin: A peptide, of about 33 amino acids, secreted by the upper INTESTINAL MUCOSA and also found in the central nervous system. It causes gallbladder contraction, release of pancreatic exocrine (or digestive) enzymes, and affects other gastrointestinal functions. Cholecystokinin may be the mediator of satiety.	2.66	3	0
ceruletide Ceruletide: A specific decapeptide obtained from the skin of Hila caerulea, an Australian amphibian. Caerulein is similar in action and composition to CHOLECYSTOKININ. It stimulates gastric, biliary, and pancreatic secretion; and certain smooth muscle. It is used in paralytic ileus and as diagnostic aid in pancreatic malfunction.. ceruletide : A decapeptide comprising 5-oxoprolyl, glutamyl, aspartyl, O-sulfotyrosyl, threonyl, glycyl, tryptopyl, methionyl, aspartyl and phenylalaninamide residues in sequence. Found in the skins of certain Australian amphibians, it is an analogue of the gastrointestinal peptide hormone cholecystokinin and stimulates gastric, biliary, and pancreatic secretion. It is used in cases of paralysis of the intestine (paralytic ileus) and as a diagnostic aid in pancreatic malfunction.	1.99	1	0	oligopeptide	diagnostic agent; gastrointestinal drug
motilin Motilin: A peptide of about 22-amino acids isolated from the DUODENUM. At low pH it inhibits gastric motor activity, whereas at high pH it has a stimulating effect.	2.91	4	0
atrial natriuretic factor Atrial Natriuretic Factor: A potent natriuretic and vasodilatory peptide or mixture of different-sized low molecular weight PEPTIDES derived from a common precursor and secreted mainly by the HEART ATRIUM. All these peptides share a sequence of about 20 AMINO ACIDS.	3.69	10	0	polypeptide
oenothein a oenothein A: from leaves of Oenothera biennis; structure given in first source	2.46	2	0
tannins gallotannin : A class of hydrolysable tannins obtained by condensation of the carboxy group of gallic acid (and its polymeric derivatives) with the hydroxy groups of a monosaccharide (most commonly glucose).	2.96	4	0	tannin
oenothein b oenothein B: from Oenothera erythrosepala Bordas; exhibits strong antitumor activity against MM2 ascites tumors & inhibits the growth of Meth-A solid-type tumors in mice; 5 alpha reductase testosterone inhibitor	3.09	4	0
thymalfasin Thymalfasin: A thymus hormone polypeptide found in thymosin fraction 5 (a crude thymus gland extract) but now produced by synthesis. It is used alone or with interferon as an immunomodulator for the treatment of CHRONIC HEPATITIS B and HEPATITIS C. Thymalfasin is also used for the treatment of chemotherapy-induced immunosuppression, and to enhance the efficacy of influenza and hepatitis B vaccines in immunocompromised patients.	2	1	0	polypeptide
glycoprotein e2, hepatitis c virus glycoprotein E2, Hepatitis C virus: RN refers to quasispecies 4E; amino acid sequence known; caution: HCV also stands for hog cholera virus	2.05	1	0
sanguiin h 6 sanguiin H 6: a cytotoxic dimeric ellagitannin from Sanguisorba officinalis; structure given in first source	2	1	0
vitisin a [no description available]	2.07	1	0	benzofurans
fullerene c70 [no description available]	2.07	1	0	fullerene
omega-conotoxin (conus magus) Conus magus toxin: from marine mollusk Conus magus; 25-27 amino acid peptide; MW 3 kDa	1.99	1	0
gastrins Gastrins: A family of gastrointestinal peptide hormones that excite the secretion of GASTRIC JUICE. They may also occur in the central nervous system where they are presumed to be neurotransmitters.	1.95	1	0
gramicidin a Gramicidin: A group of peptide antibiotics from BACILLUS brevis. Gramicidin C or S is a cyclic, ten-amino acid polypeptide and gramicidins A, B, D are linear. Gramicidin is one of the two principal components of TYROTHRICIN.	1.99	1	0
glucagon Glucagon: A 29-amino acid pancreatic peptide derived from proglucagon which is also the precursor of intestinal GLUCAGON-LIKE PEPTIDES. Glucagon is secreted by PANCREATIC ALPHA CELLS and plays an important role in regulation of BLOOD GLUCOSE concentration, ketone metabolism, and several other biochemical and physiological processes. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1511). glucagon : A 29-amino acid peptide hormone consisting of His, Ser, Gln, Gly, Thr, Phe, Thr, Ser, Asp, Tyr, Ser, Lys, Tyr, Leu, Asp, Ser, Arg, Arg, Ala, Gln, Asp, Phe, Val, Gln, Trp, Leu, Met, Asn and Thr residues joined in sequence.	1.97	1	0	peptide hormone
neuropeptide y Neuropeptide Y: A 36-amino acid peptide present in many organs and in many sympathetic noradrenergic neurons. It has vasoconstrictor and natriuretic activity and regulates local blood flow, glandular secretion, and smooth muscle activity. The peptide also stimulates feeding and drinking behavior and influences secretion of pituitary hormones.	1.98	1	0
s6c sarafotoxin sarafotoxins s6: several isotoxins from Atractaspis engaddensis; has strong cardiotoxic activity; all contain 21 amino acid residues; see also endothelium-derived vasoconstrictor factor	2.02	1	0
irl 1620 sovateltide: a potent, specific ligand for the endothelin-B receptor	2.02	1	0
tannins Tannins: Polyphenolic compounds with molecular weights of around 500-3000 daltons and containing enough hydroxyl groups (1-2 per 100 MW) for effective cross linking of other compounds (ASTRINGENTS). The two main types are HYDROLYZABLE TANNINS and CONDENSED TANNINS. Historically, the term has applied to many compounds and plant extracts able to render skin COLLAGEN impervious to degradation. The word tannin derives from the Celtic word for OAK TREE which was used for leather processing.	11.8	202	2
glucagon-like peptide 1 Glucagon-Like Peptide 1: A peptide of 36 or 37 amino acids that is derived from PROGLUCAGON and mainly produced by the INTESTINAL L CELLS. GLP-1(1-37 or 1-36) is further N-terminally truncated resulting in GLP-1(7-37) or GLP-1-(7-36) which can be amidated. These GLP-1 peptides are known to enhance glucose-dependent INSULIN release, suppress GLUCAGON release and gastric emptying, lower BLOOD GLUCOSE, and reduce food intake.	3.09	4	0
incretins Incretins: Peptides which stimulate INSULIN release from the PANCREATIC BETA CELLS following oral nutrient ingestion, or postprandially.	2.17	1	0
c-peptide C-Peptide: The middle segment of proinsulin that is between the N-terminal B-chain and the C-terminal A-chain. It is a pancreatic peptide of about 31 residues, depending on the species. Upon proteolytic cleavage of proinsulin, equimolar INSULIN and C-peptide are released. C-peptide immunoassay has been used to assess pancreatic beta cell function in diabetic patients with circulating insulin antibodies or exogenous insulin. Half-life of C-peptide is 30 min, almost 8 times that of insulin.	2.49	2	0
cellulose DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.	8.93	12	0	glycoside
ceftiofur ceftiofur: structure in first source	2.25	1	0
perovskite calcium titanate : A calcium salt with the formula CaTiO3, generally obtained in the form of the mineral perovskite.	2.05	1	0
endothelin-1 Endothelin-1: A 21-amino acid peptide produced in a variety of tissues including endothelial and vascular smooth-muscle cells, neurons and astrocytes in the central nervous system, and endometrial cells. It acts as a modulator of vasomotor tone, cell proliferation, and hormone production. (N Eng J Med 1995;333(6):356-63)	2.69	3	0
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	3.71	10	0	1,2-diacyl-sn-glycero-3-phosphocholine
chlorophyll a Chlorophyll: Porphyrin derivatives containing magnesium that act to convert light energy in photosynthetic organisms.. chlorophyll : A family of magnesium porphyrins, defined by the presence of a fifth ring beyond the four pyrrole-like rings. The rings can have various side chains which usually include a long phytol chain.	3.45	7	0	chlorophyll; methyl ester	cofactor
bismuth subsalicylate bismuth subsalicylate: bismuth subsalicylate is the active ingredient of Pepto-Bismol and in Kaopectate; used to treat nausea, heartburn, indigestion, upset stomach, diarrhea and other temporary discomforts of the stomach; used with Azoles and other drugs to treat Helicobacter. bismuth subsalicylate : A bismuth salt of salicylic acid.	1.97	1	0
bismuth subgallate bismuth subgallate: RN given refers to parent cpd	11.65	38	6
thimerosal Thimerosal: An ethylmercury-sulfidobenzoate that has been used as a preservative in VACCINES; ANTIVENINS; and OINTMENTS. It was formerly used as a topical antiseptic. It degrades to ethylmercury and thiosalicylate.. thimerosal : An alkylmercury compound (approximately 49% mercury by weight) used as an antiseptic and antifungal agent.	2.72	3	0	alkylmercury compound	antifungal drug; antiseptic drug; disinfectant; drug allergen
ubiquinone Ubiquinone: A lipid-soluble benzoquinone which is involved in ELECTRON TRANSPORT in mitochondrial preparations. The compound occurs in the majority of aerobic organisms, from bacteria to higher plants and animals.	2	1	0
calpain Calpain: Cysteine proteinase found in many tissues. Hydrolyzes a variety of endogenous proteins including NEUROPEPTIDES; CYTOSKELETAL PROTEINS; proteins from SMOOTH MUSCLE; CARDIAC MUSCLE; liver; platelets; and erythrocytes. Two subclasses having high and low calcium sensitivity are known. Removes Z-discs and M-lines from myofibrils. Activates phosphorylase kinase and cyclic nucleotide-independent protein kinase. This enzyme was formerly listed as EC 3.4.22.4.	7.99	4	0
lucifer yellow lucifer yellow: RN given refers to di-Li salt	2.39	2	0	organic lithium salt	fluorochrome
2-hydroxyursolic acid 2-hydroxyursolic acid: isolated from the stem bark of Physocarpus intermedius; structure in first source	2.08	1	0
theaflavin-3,3'-digallate theaflavin-3,3'-digallate: structure in first source	2	1	0
spongia-13(16),14-dien-19-oic acid spongia-13(16),14-dien-19-oic acid : A tetracyclic diterpenoid that is 3b,4,5,5a,6,7,8,9,9a,9b,10,11-dodecahydrophenanthro[1,2-c]furan substituted by methyl groups at positions 3b, 6 and 9 and a carboxy group at position 6. Isolated from Spongia, it exhibits inhibitory activity against androgen receptor.	2.17	1	0	cyclic ether; monocarboxylic acid; tetracyclic diterpenoid	androgen antagonist; metabolite
roquefortine [no description available]	2.17	1	0	pyrroloindole
oxypaeoniflora oxypaeoniflora: from Paeonia lactiflora	2.49	2	0	4-hydroxybenzoate ester; beta-D-glucoside; bridged compound; cyclic acetal; lactol; monoterpene glycoside	plant metabolite
3-(3,4-dihydroxyphenyl)lactate 3-(3,4-dihydroxyphenyl)lactate : A hydroxy monocarboxylic acid anion that is the conjugate base of 3-(3,4-dihydroxyphenyl)lactic acid; major species at pH 7.3.	2.17	1	0	hydroxy monocarboxylic acid anion
chitosan [no description available]	7.43	75	0
alpha-pyrone-4,6-dicarboxylic acid alpha-pyrone-4,6-dicarboxylic acid: structure. 2-oxo-2H-pyran-4,6-dicarboxylate : A dicarboxylic acid dianion obtained via deprotonation of both carboxy groups of 2-oxo-2H-pyran-4,6-dicarboxylic acid; major species at pH 7.3.	1.96	1	0	dicarboxylic acid dianion
s-propargylcysteine S-propargylcysteine: a memory enhancing agent; structure in first source	2.21	1	0
balanophonin balanophonin: from fruit wall of Cirsium vulgare; structure in first source	2.41	1	0
s-nitro-n-acetylpenicillamine S-nitro-N-acetylpenicillamine: a NO donor	2.01	1	0
bucladesine Bucladesine: A cyclic nucleotide derivative that mimics the action of endogenous CYCLIC AMP and is capable of permeating the cell membrane. It has vasodilator properties and is used as a cardiac stimulant. (From Merck Index, 11th ed). bucladesine : A 3',5'-cyclic purine nucleotide that is the 2'-butanoate ester and 6-N-butanoyl derivative of 3',5'-cyclic AMP.	4.17	17	0	3',5'-cyclic purine nucleotide
potassium iodate [no description available]	2.01	1	0
sodium bisulfite sodium bisulfite: has been used externally for parasitic skin diseases and as gastrointestinal antiseptic; structure. sodium hydrogensulfite : An inorganic sodium salt having hydrogensulfite as the counterion.	2.06	1	0	inorganic sodium salt; sulfite salt	allergen; food antioxidant; food colour retention agent; mutagen; reducing agent
methyl orange methyl orange: indictor of pH with strong acids & bases; also used as reagent to form ion pairs with, and thereby isolate, certain compounds from biological material; minor descriptor (75-86); on-line & INDEX MEDICUS search AZO COMPOUNDS (75-86); file maintained to Azo cpds	2.15	1	0
stearates Stearates: Salts and esters of the 18-carbon saturated, monocarboxylic acid--stearic acid.	1.96	1	0
sodium glutamate Sodium Glutamate: One of the FLAVORING AGENTS used to impart a meat-like flavor.. monosodium glutamate : An organic sodium salt that is the monosodium salt of glutamic acid.	2.42	2	0	monosodium glutamate	flavouring agent
ro13-9904 Ceftriaxone: A broad-spectrum cephalosporin antibiotic and cefotaxime derivative with a very long half-life and high penetrability to meninges, eyes and inner ears.. ceftriaxone : A third-generation cephalosporin compound having 2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetylamino and [(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl side-groups.	2.25	1	0
mersalyl Mersalyl: A toxic thiol mercury salt formerly used as a diuretic. It inhibits various biochemical functions, especially in mitochondria, and is used to study those functions.	2.37	2	0
chiniofon Hydroxyquinolines: The 8-hydroxy derivatives inhibit various enzymes and their halogenated derivatives, though neurotoxic, are used as topical anti-infective agents, among other uses.	2.11	1	0
methyl jasmonate [no description available]	2.25	1	0
rubusoside rubusoside: from RUBUS. rubusoside : A steviol glycoside that is steviol in which both the carboxy group and the tertiary allylic hydroxy group have been converted to their corresponding beta-D-glucosides. A precious bioactive natural sweetener which mainly exists the in Chinese sweet tea plant, Rubus suavissimus.	2.05	1	0	beta-D-glucoside; bridged compound; steviol glycoside; tetracyclic diterpenoid	plant metabolite; sweetening agent
s-adenosylmethionine (R)-S-adenosyl-L-methionine : An S-adenosyl-L-methionine that has R-configuration.. S-adenosyl-L-methionine zwitterion : A zwitterionic tautomer of S-adenosyl-L-methionine arising from shift of the proton from the carboxy group to the amino group.. (R)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has R-configuration; major species at pH 7.3.. (S)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has S-configuration; major species at pH 7.3.. S-adenosyl-L-methionine : A sulfonium compound that is the S-adenosyl derivative of L-methionine. It is an intermediate in the metabolic pathway of methionine.	1.98	1	0	organic cation; sulfonium compound	coenzyme; cofactor; human metabolite; micronutrient; Mycoplasma genitalium metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
marinopyrrole a marinopyrrole A: antibiotic from a marine Streptomyces sp.; structure in first source. (-)-marinopyrrole A : A member of the class of pyrroles that is 1'H-1,3'-bipyrrole substituted by four chloro groups at positions 4, 4', 5 and 5' and two 2-hydroxybenzoyl moieties at positions 2 and 2'. It is isolated from Streptomyces sp.CNQ-418 and exhibits cytotoxic and antibacterial activities.	2.17	1	0	aromatic ketone; organochlorine compound; phenols; pyrroles	antibacterial agent; antimicrobial agent; antineoplastic agent; bacterial metabolite; marine metabolite
ethyl cellulose [no description available]	2.6	1	0	glycoside
colletoic acid colletoic acid: an 11beta-hydroxysteroid dehydrogenase type 1 inhibitor from Colletotrichum gloeosporioides; structure in first source	2.17	1	0
albiflorin albiflorin: glucoside in peony roots. albiflorin : A monoterpene glycoside with formula C23H28O11, originally isolated from the roots of Paeonia lactiflora.	3.5	7	0	benzoate ester; beta-D-glucoside; bridged compound; gamma-lactone; monoterpene glycoside; secondary alcohol	neuroprotective agent; plant metabolite
4,4-difluoro-4-bora-3a,4a-diaza-s-indacene [no description available]	2.03	1	0	BODIPY compound
cardiovascular agents Cardiovascular Agents: Agents that affect the rate or intensity of cardiac contraction, blood vessel diameter, or blood volume.	2.44	2	0
neurotensin neurotensin, Tyr(11)-: RN given refers to parent cpd & (D)-isomer; RN for cpd without isomeric designation not avail 5/91	1.99	1	0	peptide hormone	human metabolite; mitogen; neurotransmitter; vulnerary
mannans [no description available]	3.43	7	0
ipomoeassin f ipomoeassin F: a cytotoxic macrocyclic glycoresin from the leaves of Ipomoea squamosa from the Suriname rainforest	2.17	1	0
peptones Peptones: Derived proteins or mixtures of cleavage products produced by the partial hydrolysis of a native protein either by an acid or by an enzyme. Peptones are readily soluble in water, and are not precipitable by heat, by alkalis, or by saturation with ammonium sulfate. (Dorland, 28th ed)	1.97	1	0
glycolipids [no description available]	2.21	1	0
piperidines Piperidines: A family of hexahydropyridines.	4.08	15	0
6,8-dihydroxy-2,2,4,4-tetramethyl-7-(3-methylbutanoyl)-9-(2-methylpropyl)-9h-xanthene-1,3-dione [no description available]	2.17	1	0	xanthenes
thymosin Thymosin: Thymosin. A family of heat-stable, polypeptide hormones secreted by the thymus gland. Their biological activities include lymphocytopoiesis, restoration of immunological competence and enhancement of expression of T-cell characteristics and function. They have therapeutic potential in patients having primary or secondary immunodeficiency diseases, cancer or diseases related to aging.	2	1	0
7-hydroxymitragynine 7-hydroxymitragynine: an orally active opioid analgesic from the Thai medicinal herb Mitragyna speciosa; structure in first source	2.17	1	0	alkaloid
interleukin-8 Interleukin-8: A member of the CXC chemokine family that plays a role in the regulation of the acute inflammatory response. It is secreted by variety of cell types and induces CHEMOTAXIS of NEUTROPHILS and other inflammatory cells.	8.15	5	0
mauritianin mauritianin: from Chenopodium quinoa	2.06	1	0
antibiotic cv-1 [no description available]	2.02	1	0
anagliptin anagliptin: anagliptin hydrochloride salt is the active compound	3.27	1	0	amino acid amide
dorrigocin b dorrigocin B: isolated from the fermentation broth & mycelium of Streptomyces platensis; structure given in first source	2.17	1	0
dorrigocin a dorrigocin A: isolated from the fermentation broth & mycelium of Streptomyces platensis; structure given in first source	2.17	1	0
typhaneoside typhaneoside: isolated from pollen of Typha angustfolia L. (puhuang); structure given in first source	2.21	1	0	flavonoids; glycoside
hamamelitannin hamamelitannin: cytotoxic from witch hazel (Hamamelis virginiana); structure in first source	11.05	21	0	gallate ester
phillyrin [no description available]	2.11	1	0
gypenoside XVII gypenoside XVII : A ginsenoside found in Panax species that is dammarane which is substituted by hydroxy groups at the 3beta, 12beta and 20 pro-S positions, in which the hydroxy groups at positions 3 and 20 have been converted to the corresponding beta-D-glucopyranoside and beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranoside respectively, and in which a double bond has been introduced at the 24-25 position.	2.49	2	0	12beta-hydroxy steroid; beta-D-glucoside; disaccharide derivative; ginsenoside; tetracyclic triterpenoid	plant metabolite
punicalagin punicalagin: hepatoprotective agent isolated from Terminalia catappa; structure in first source	8.86	11	0	tannin
tylosin [no description available]	2.21	1	0
mk-3102 [no description available]	3.27	1	0	pyrrolopyrazole
peoniflorin [no description available]	2.07	1	0
benzoylpaeoniflorin benzoylpaeoniflorin: from Paeonia lactiflora	2.31	1	0
galloylpaeoniflorin galloylpaeoniflorin: an acylated monoterpene glucoside from paeony root; structure in first source	2.76	3	0
methylcellulose Methylcellulose: Methylester of cellulose. Methylcellulose is used as an emulsifying and suspending agent in cosmetics, pharmaceutics and the chemical industry. It is used therapeutically as a bulk laxative.	7.15	1	0
isoquercitrin [no description available]	3.18	5	0
bocillin fl BOCILLIN FL: used for detecting pencillin-binding proteins; structure in first source	2.02	1	0
tatanan a tatanan A: from the rhizomes of Acorus tatarinowii Schott; structure in first source	2.17	1	0
vasoactive intestinal peptide Vasoactive Intestinal Peptide: A highly basic, 28 amino acid neuropeptide released from intestinal mucosa. It has a wide range of biological actions affecting the cardiovascular, gastrointestinal, and respiratory systems and is neuroprotective. It binds special receptors (RECEPTORS, VASOACTIVE INTESTINAL PEPTIDE).	1.98	1	0
natriuretic peptide, brain Natriuretic Peptide, Brain: A PEPTIDE that is secreted by the BRAIN and the HEART ATRIA, stored mainly in cardiac ventricular MYOCARDIUM. It can cause NATRIURESIS; DIURESIS; VASODILATION; and inhibits secretion of RENIN and ALDOSTERONE. It improves heart function. It contains 32 AMINO ACIDS.	2.17	1	0	polypeptide
heme Heme: The color-furnishing portion of hemoglobin. It is found free in tissues and as the prosthetic group in many hemeproteins.. ferroheme : Any iron(II)--porphyrin coordination complex.. ferroheme b : Heme b in which the iron has oxidation state +2.. heme : A heme is any tetrapyrrolic chelate of iron.	2.31	1	0
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	9.89	116	1	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
novobiocin Novobiocin: An antibiotic compound derived from Streptomyces niveus. It has a chemical structure similar to coumarin. Novobiocin binds to DNA gyrase, and blocks adenosine triphosphatase (ATPase) activity. (From Reynolds, Martindale The Extra Pharmacopoeia, 30th ed, p189). novobiocin : A coumarin-derived antibiotic obtained from Streptomyces niveus.	3.1	1	0	carbamate ester; ether; hexoside; hydroxycoumarin; monocarboxylic acid amide; monosaccharide derivative; phenols	antibacterial agent; antimicrobial agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; Escherichia coli metabolite; hepatoprotective agent
tetracycline Tetracycline: A naphthacene antibiotic that inhibits AMINO ACYL TRNA binding during protein synthesis.. tetracycline : A broad-spectrum polyketide antibiotic produced by the Streptomyces genus of actinobacteria.	4.88	10	0
chlortetracycline Chlortetracycline: A TETRACYCLINE with a 7-chloro substitution.. chlortetracycline : A member of the class of tetracyclines with formula C22H23ClN2O8 isolated from Streptomyces aureofaciens.	3.58	9	0
oxytetracycline, anhydrous Oxytetracycline: A TETRACYCLINE analog isolated from the actinomycete STREPTOMYCES RIMOSUS and used in a wide variety of clinical conditions.. oxytetracycline : A tetracycline used for treatment of infections caused by a variety of Gram positive and Gram negative microorganisms including Mycoplasma pneumoniae, Pasteurella pestis, Escherichia coli, Haemophilus influenzae (respiratory infections), and Diplococcus pneumoniae.	2.35	2	0
isoascorbic acid isoascorbic acid: food antioxidant; (L)-isomer is ascorbic acid; RN given refers to (D)-isomer; structure	2.44	2	0	ascorbic acid
salicylates Salicylates: The salts or esters of salicylic acids, or salicylate esters of an organic acid. Some of these have analgesic, antipyretic, and anti-inflammatory activities by inhibiting prostaglandin synthesis.. hydroxybenzoate : Any benzoate derivative carrying a single carboxylate group and at least one hydroxy substituent.. salicylates : Any salt or ester arising from reaction of the carboxy group of salicylic acid, or any ester resulting from the condensation of the phenolic hydroxy group of salicylic acid with an organic acid.. salicylate : A monohydroxybenzoate that is the conjugate base of salicylic acid.	3.35	7	0	monohydroxybenzoate	plant metabolite
piroxicam [no description available]	2.4	2	0	benzothiazine; monocarboxylic acid amide; pyridines	analgesic; antirheumatic drug; cyclooxygenase 1 inhibitor; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-steroidal anti-inflammatory drug
warfarin Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.	4.37	20	0	benzenes; hydroxycoumarin; methyl ketone
6-o-palmitoylascorbic acid [no description available]	2.76	3	0	fatty acid ester
4-hydroxycoumarin 2-hydroxychromone: structure	3.1	1	0	hydroxycoumarin
hispidin hispidin: metabolite of Basidiomycete Polyporus hispidus. hispidin : Fungal metabolite first found in basidiomycete Inonotus hispidus (formerly Polyporus hispidus).	7.53	2	0	2-pyranones; catechols	antioxidant; EC 2.7.11.13 (protein kinase C) inhibitor; fungal metabolite
ilicicolin h ilicicolin H: structure in first source. ilicicolin H : An aromatic ketone in which the ketone carbonyl group is attached to a (1R,2R,4aS,7S,8aR)-4,7-dimethyl-1-[(1E)-prop-1-en-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-yl group and a 4-hydroxy-5-(4-hydroxyphenyl)-2-oxo-1,2-dihydropyridin-3-yl group. Isolated from the from the "imperfect" fungus Cylindrocladium iliciola strain MFC-870.	2.17	1	0	aromatic ketone; carbobicyclic compound; ilicicolin; monohydroxypyridine; octahydronaphthalenes; phenols; pyridone	antimicrobial agent; mitochondrial respiratory-chain inhibitor
11-o-galloylbergenin 11-O-galloylbergenin: analgesic and anti-inflammatory; structure in first source	3.48	7	0
betalains Betalains: Compounds derived from TYROSINE via betalamic acid, including BETAXANTHINS and BETACYANINS. They are found in the Caryophyllales order of PLANTS and some BASIDIOMYCETES.	2.63	2	0
epidermal growth factor Epidermal Growth Factor: A 6-kDa polypeptide growth factor initially discovered in mouse submaxillary glands. Human epidermal growth factor was originally isolated from urine based on its ability to inhibit gastric secretion and called urogastrone. Epidermal growth factor exerts a wide variety of biological effects including the promotion of proliferation and differentiation of mesenchymal and EPITHELIAL CELLS. It is synthesized as a transmembrane protein which can be cleaved to release a soluble active form.	3.09	5	0
gastrin-releasing peptide Gastrin-Releasing Peptide: Neuropeptide and gut hormone that helps regulate GASTRIC ACID secretion and motor function. Once released from nerves in the antrum of the STOMACH, the neuropeptide stimulates release of GASTRIN from the GASTRIN-SECRETING CELLS.	1.97	1	0
kaolinite Kaolin: The most common mineral of a group of hydrated aluminum silicates, approximately H2Al2Si2O8-H2O. It is prepared for pharmaceutical and medicinal purposes by levigating with water to remove sand, etc. (From Merck Index, 11th ed) The name is derived from Kao-ling (Chinese: high ridge), the original site. (From Grant & Hackh's Chemical Dictionary, 5th ed). kaolin : An aluminosilicate soft white mineral named after the hill in China (Kao-ling) from which it was mined for centuries. In its natural state kaolin is a white, soft powder consisting principally of the mineral kaolinite, and varying amounts of other minerals such as muscovite, quartz, feldspar, and anatase. It is used in the manufacture of china and porcelain and also widely used in the production of paper, rubber, paint, drying agents, and many other products.	2.88	1	0	aluminosilicate mineral; mixture	antidiarrhoeal drug; excipient
clay Clay: A naturally-occurring rock or soil constituent characterized by particles with a diameter of less than 0.005 mm. It is composed primarily of hydrous aluminum silicates, trace amounts of metal OXIDES, and organic matter.	7.69	2	0
charybdotoxin [no description available]	2.68	3	0
transforming growth factor beta Transforming Growth Factor beta: A factor synthesized in a wide variety of tissues. It acts synergistically with TGF-alpha in inducing phenotypic transformation and can also act as a negative autocrine growth factor. TGF-beta has a potential role in embryonal development, cellular differentiation, hormone secretion, and immune function. TGF-beta is found mostly as homodimer forms of separate gene products TGF-beta1, TGF-beta2 or TGF-beta3. Heterodimers composed of TGF-beta1 and 2 (TGF-beta1.2) or of TGF-beta2 and 3 (TGF-beta2.3) have been isolated. The TGF-beta proteins are synthesized as precursor proteins.	3.33	6	0
myricetin-3-o-rhamnoside myricetin-3-O-rhamnoside: antioxidant and antigenotoxic from Myrtus communis; structure in first source	2.55	2	0
okadaic acid Okadaic Acid: A specific inhibitor of phosphoserine/threonine protein phosphatase 1 and 2a. It is also a potent tumor promoter. It is produced by DINOFLAGELLATES and causes diarrhetic SHELLFISH POISONING.. okadaic acid : A polycyclic ether that is produced by several species of dinoflagellates, and is known to accumulate in both marine sponges and shellfish. A polyketide, polyether derivative of a C38 fatty acid, it is one of the primary causes of diarrhetic shellfish poisoning (DSP). It is a potent inhibitor of specific protein phosphatases and is known to have a variety of negative effects on cells.	2.68	3	0	ketal
tatanan b tatanan B: from the rhizomes of Acorus tatarinowii Schott; structure in first source	2.53	2	0
chebulic acid chebulic acid: from the ripe fruits of Terminalia chebula	2.17	1	0
gracilioether f gracilioether F: structure in first source	2.17	1	0
agar Agar: A complex sulfated polymer of galactose units, extracted from Gelidium cartilagineum, Gracilaria confervoides, and related red algae. It is used as a gel in the preparation of solid culture media for microorganisms, as a bulk laxative, in making emulsions, and as a supporting medium for immunodiffusion and immunoelectrophoresis.. agar : A complex mixture of polysaccharides extracted from species of red algae. Its two main components are agarose and agaropectin. Agarose is the component responsible for the high-strength gelling properties of agar, while agaropectin provides the viscous properties.	1.94	1	0
hypophyllanthin hypophyllanthin: Anti-inflammatory from Phyllanthus amarus	8.31	1	0
cryptocaryol a cryptocaryol A: from Cryptocarya spp.; structure in first source. cryptocaryol A : A member of the class of 2-pyranones that is 5,6-dihydro-2H-pyran-2-one substituted by a 2,4,6,8,10-pentahydroxypentacosyl group at position 6. It has been isolated from Cryptocarya species.	2.17	1	0	2-pyranones; pentol	plant metabolite
cyclin d1 Cyclin D1: Protein encoded by the bcl-1 gene which plays a critical role in regulating the cell cycle. Overexpression of cyclin D1 is the result of bcl-1 rearrangement, a t(11;14) translocation, and is implicated in various neoplasms.	2.49	2	0
caseins Caseins: A mixture of related phosphoproteins occurring in milk and cheese. The group is characterized as one of the most nutritive milk proteins, containing all of the common amino acids and rich in the essential ones.	4.61	10	0
butobendin butobendin: RN refers to (S-(R,R))-isomer; Craviten is tradename; structure given in first source	1.96	1	0
thearubigin thearubigin: from black tea leaves; a catechin oxidized product; a mixture of heterogenous polyphenols	3.27	6	0
ellagitannin ellagitannin: structure; precoxin A/ praecoxin A is a purified ellagitannin. ellagitannin : A form of hydrolysable tannin produced from ellagic acid. Ellagitannins are glucosides which are readily hydrolysed by water to regenerate ellagic acid when the plants are eaten.	10.3	16	0
phthalocyanine phthalocyanine : A tetrapyrrole fundamental parent that consists of four isoindole-type units, with the connecting carbon atoms in the macrocycle replaced by nitrogen.	7.6	1	0	phthalocyanines; tetrapyrrole fundamental parent
nitrophenols Nitrophenols: PHENOLS carrying nitro group substituents.	2.65	3	0
bassianolide bassianolide: cyclodepsipeptide from mycelia of Beauveria bassiana; inhibits isotonic contractions induced by acetylcholine. bassianolide : A cyclodepsipeptide consisting of a cyclic tetramer of the depsipeptide D-Hiv-N-methyl-L-leucine (where D-Hiv = D-alpha-hydroxyisovaleric acid). Found in the fungal species Beauveria bassiana and Verticillium lecanii, it has insecticidal properties and is used as a commercial biopesticide to control of insects of agricultural, veterinary and medical significance. For elucidation of the structure, see Suzuki et al., Tetrahedron Lett. 1977 v25, 2167-2170.	2.31	1	0	cyclodepsipeptide; cyclooctadepsipeptide	antineoplastic agent; fungal metabolite; insecticide
norbergenin norbergenin: bergenin derivative isolated from the root of Ardisia crenata	2.13	1	0
neuropeptide y, leu(31)-pro(34)- neuropeptide Y, Leu(31)-Pro(34)-: specific Y1 receptor agonist	1.98	1	0
angiotensin i Angiotensin I: A decapeptide that is cleaved from precursor angiotensinogen by RENIN. Angiotensin I has limited biological activity. It is converted to angiotensin II, a potent vasoconstrictor, after the removal of two amino acids at the C-terminal by ANGIOTENSIN CONVERTING ENZYME.. angiotensin I : A ten amino acid peptide formed by renin cleavage of angiotensinogen. Angiotensin I has no direct biological function except that high levels can stimulate catecholamine production. It is metabolized to its biologically active byproduct angiotensin II, a potent vasoconstrictor, by angiotensin converting enzyme (ACE) through cleavage of the two terminal amino acids.. angiotensin I dizwitterion : A peptide zwitterion that is the dizwitterionic form of angiotensin I having both carboxy groups deprotonated and the aspartyl amino group and arginine side-chain protonated. It is the major species at pH 7.3.	1.97	1	0	angiotensin; peptide zwitterion	human metabolite; neurotransmitter agent
hyaluronoglucosaminidase Hyaluronoglucosaminidase: An enzyme that catalyzes the random hydrolysis of 1,4-linkages between N-acetyl-beta-D-glucosamine and D-glucuronate residues in hyaluronate. (From Enzyme Nomenclature, 1992) There has been use as ANTINEOPLASTIC AGENTS to limit NEOPLASM METASTASIS.	2.99	4	0
tetrahydroamentoflavone tetrahydroamentoflavone: isolated from Semecarpus anacardium; structure in first source	2.58	2	0
amyloid beta-peptides amyloid beta-protein (1-28): binding of synthetic beta-amyloid peptide fragments to glycosaminoglycan is pH-dependent	2.07	1	0
diospyros Diospyros: A plant genus of the family EBENACEAE, order Ebenales, subclass Dilleniidae, class Magnoliopsida best known for the edible fruit and the antibacterial activity and compounds of the wood.	3.74	9	0
ginkgolide b [no description available]	2.38	2	0
morroniside morroniside: from Cornus officinalis; protects cultured human umbilical vein endothelial cells from damage by high ambient glucose; a component of cornel iridoid glycoside; structure in first source	2.04	1	0
chebulinic acid chebulinic acid: one of the allagitannins in the seeds of Euphoria longana; structure given in first source	8.56	8	0
chebulagic acid [no description available]	3.42	7	0
gibberellins [no description available]	2.08	1	0
hexenuronic acid [no description available]	2.06	1	0
nonactin nonactin: macrolide tetrolide antibiotic isolated from cycloheximide-producing species of Streptomyces; minor descriptor (75-86); on-line & INDEX MEDICUS search ANTIBIOTICS (75-86)	1.99	1	0
casuarictin casuarictin: RN given refers to beta-D-Glc stereoisomer; RN for cpd without isomeric designation not avail 3/92; precursor of ellagic acid; structure given in first source	3.33	6	0
peoniflorin peoniflorin: from Radix and of Paeonia suffruticosa	4.29	17	0
vitamin b 12 Vitamin B 12: A cobalt-containing coordination compound produced by intestinal micro-organisms and found also in soil and water. Higher plants do not concentrate vitamin B 12 from the soil and so are a poor source of the substance as compared with animal tissues. INTRINSIC FACTOR is important for the assimilation of vitamin B 12.	4.05	3	1
s 8932 [no description available]	2.31	1	0	aromatic amine; C-nucleoside; carboxylic ester; nitrile; phosphoramidate ester; pyrrolotriazine	anticoronaviral agent; antiviral drug; prodrug
cyclosporine Cyclosporine: A cyclic undecapeptide from an extract of soil fungi. It is a powerful immunosupressant with a specific action on T-lymphocytes. It is used for the prophylaxis of graft rejection in organ and tissue transplantation. (From Martindale, The Extra Pharmacopoeia, 30th ed).	2.71	3	0
blasticidin s blasticidin S: RN given refers to (S)-isomer; structure. blasticidin S : A blasticidin that is an antibiotic obtained from Streptomyces griseochromogene.	3.23	1	0
silybin Silybin: The major active component of silymarin flavonoids extracted from seeds of the MILK THISTLE, Silybum marianum; it is used in the treatment of HEPATITIS; LIVER CIRRHOSIS; and CHEMICAL AND DRUG INDUCED LIVER INJURY, and has antineoplastic activity; silybins A and B are diastereomers.	2.79	3	0
peptide yy Peptide YY: A 36-amino acid peptide produced by the L cells of the distal small intestine and colon. Peptide YY inhibits gastric and pancreatic secretion.. peptide YY : A 36-membered human gut polypeptide consisting of Tyr, Pro, Ile, Lys, Pro, Glu, Ala, Pro, Gly, Glu, Asp, Ala, Ser, Pro, Glu, Glu, Leu, Asn, Arg, Tyr, Tyr, Ala, Ser, Leu, Arg, His, Tyr, Leu, Asn, Leu, Val, Thr, Arg, Gln, Arg and Tyr-NH2 residues joined in sequence.	2.74	3	0
lactoferrin Lactoferrin: An iron-binding protein that was originally characterized as a milk protein. It is widely distributed in secretory fluids and is found in the neutrophilic granules of LEUKOCYTES. The N-terminal part of lactoferrin possesses a serine protease which functions to inactivate the TYPE III SECRETION SYSTEM used by bacteria to export virulence proteins for host cell invasion.	7.76	2	0
digitonin Digitonin: A glycoside obtained from Digitalis purpurea; the aglycone is digitogenin which is bound to five sugars. Digitonin solubilizes lipids, especially in membranes and is used as a tool in cellular biochemistry, and reagent for precipitating cholesterol. It has no cardiac effects.. digitonin : A spirostanyl glycoside that is digitogenin in which the 3-hydroxy group is substituted by a beta-D-glucopyranosyl-(1->3)-beta-D-galactopyranosyl-(1->2)-[beta-D-xylopyranosyl-(1->3)]-beta-D-glucopyranosyl-(1->4)-beta-D-galactopyranosyl group. It is a steroidal saponin isolated from the foxglove plant, Digitalis purpurea. It is used extensively as a mild non-ionic detergent for extracting proteins from membranes for structure and function studies.	1.97	1	0
catalpol catalpol: component of dihuang; RN given refers to (1aS-(1aalpha,1bbeta,2beta,5abeta,6beta,6aalpha))-isomer; RN for cpd without isomeric designation not avail 12/92	2.31	1	0
masticadienolic acid masticadienolic acid: an antifungal agent from Pistacia terebinthus galls; structure in first source	2.17	1	0
beta-amyrin palmitate beta-amyrin palmitate: alpha-amyrin palmitate is also available; may activate noradrenergic activity	2.11	1	0
jarosite [no description available]	7.25	1	0
vanadium diascorbate vanadium diascorbate: structure given in first source	2.4	2	0
orabase Orabase: used in therapy of oral mucosal ulcers	2.13	1	0
apyrase Apyrase: A calcium-activated enzyme that catalyzes the hydrolysis of ATP to yield AMP and orthophosphate. It can also act on ADP and other nucleoside triphosphates and diphosphates. EC 3.6.1.5.	2.13	1	0
thromboplastin Thromboplastin: Constituent composed of protein and phospholipid that is widely distributed in many tissues. It serves as a cofactor with factor VIIa to activate factor X in the extrinsic pathway of blood coagulation.	2.88	4	0
muramidase Muramidase: A basic enzyme that is present in saliva, tears, egg white, and many animal fluids. It functions as an antibacterial agent. The enzyme catalyzes the hydrolysis of 1,4-beta-linkages between N-acetylmuramic acid and N-acetyl-D-glucosamine residues in peptidoglycan and between N-acetyl-D-glucosamine residues in chitodextrin. EC 3.2.1.17.	4.02	14	0
amyloid beta-peptides amyloid beta-protein (1-40): although acutely neurotoxic in both rat & monkey cerebral cortex, neuronal degeneration in primates resembles more closely to that found in Alzheimer's disease; amino acid sequence has been determined	2.55	2	0
exudates Malaysia: A parliamentary democracy with a constitutional monarch in southeast Asia, consisting of 11 states (West Malaysia) on the Malay Peninsula and two states (East Malaysia) on the island of BORNEO. It is also called the Federation of Malaysia. Its capital is Kuala Lumpur. Before 1963 it was the Union of Malaya. It reorganized in 1948 as the Federation of Malaya, becoming independent from British Malaya in 1957 and becoming Malaysia in 1963 as a federation of Malaya, Sabah, Sarawak, and Singapore (which seceded in 1965). The form Malay- probably derives from the Tamil malay, mountain, with reference to its geography. (From Webster's New Geographical Dictionary, 1988, p715 & Room, Brewer's Dictionary of Names, 1992, p329)	2.74	3	0
neuropeptide y (13-36) [no description available]	1.98	1	0
acyclovir Acyclovir: A GUANOSINE analog that acts as an antimetabolite. Viruses are especially susceptible. Used especially against herpes.. acyclovir : An oxopurine that is guanine substituted by a (2-hydroxyethoxy)methyl substituent at position 9. Used in the treatment of viral infections.	2.74	3	0	2-aminopurines; oxopurine	antimetabolite; antiviral drug
cyclic gmp Cyclic GMP: Guanosine cyclic 3',5'-(hydrogen phosphate). A guanine nucleotide containing one phosphate group which is esterified to the sugar moiety in both the 3'- and 5'-positions. It is a cellular regulatory agent and has been described as a second messenger. Its levels increase in response to a variety of hormones, including acetylcholine, insulin, and oxytocin and it has been found to activate specific protein kinases. (From Merck Index, 11th ed). 3',5'-cyclic GMP : A 3',5'-cyclic purine nucleotide in which the purine nucleobase is specified as guanidine.	3.58	9	0	3',5'-cyclic purine nucleotide; guanyl ribonucleotide	Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
deoxyguanosine [no description available]	7.42	2	0	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
guanosine diphosphate Guanosine Diphosphate: A guanine nucleotide containing two phosphate groups esterified to the sugar moiety.	2.4	2	0	guanosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	Escherichia coli metabolite; mouse metabolite; uncoupling protein inhibitor
guanosine triphosphate Guanosine Triphosphate: Guanosine 5'-(tetrahydrogen triphosphate). A guanine nucleotide containing three phosphate groups esterified to the sugar moiety.	2.94	4	0	guanosine 5'-phosphate; purine ribonucleoside 5'-triphosphate	Escherichia coli metabolite; mouse metabolite; uncoupling protein inhibitor
hypoxanthine [no description available]	2.02	1	0	nucleobase analogue; oxopurine; purine nucleobase	fundamental metabolite
inosine [no description available]	2.36	2	0	inosines; purines D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
inosine triphosphate Inosine Triphosphate: Inosine 5'-(tetrahydrogen triphosphate). An inosine nucleotide containing three phosphate groups esterified to the sugar moiety. Synonym: IRPPP.	2.38	2	0	inosine phosphate; purine ribonucleoside 5'-triphosphate	Escherichia coli metabolite; human metabolite; mouse metabolite
folic acid folcysteine: used to promote fertility in chickens. vitamin B9 : Any B-vitamin that exhibits biological activity against vitamin B9 deficiency. Vitamin B9 refers to the many forms of folic acid and its derivatives, including tetrahydrofolic acid (the active form), methyltetrahydrofolate (the primary form found in blood), methenyltetrahydrofolate, folinic acid amongst others. They are present in abundance in green leafy vegetables, citrus fruits, and animal products. Lack of vitamin B9 leads to anemia, a condition in which the body cannot produce sufficient number of red blood cells. Symptoms of vitamin B9 deficiency include fatigue, muscle weakness, and pale skin.	4.81	7	1	folic acids; N-acyl-amino acid	human metabolite; mouse metabolite; nutrient
3-methyladenine N3-methyladenine: structure in first source	1.96	1	0
guanosine 5'-o-(3-thiotriphosphate) Guanosine 5'-O-(3-Thiotriphosphate): Guanosine 5'-(trihydrogen diphosphate), monoanhydride with phosphorothioic acid. A stable GTP analog which enjoys a variety of physiological actions such as stimulation of guanine nucleotide-binding proteins, phosphoinositide hydrolysis, cyclic AMP accumulation, and activation of specific proto-oncogenes.	2.43	2	0	nucleoside triphosphate analogue
pheophytin a pheophytin a: structure given in first source; RN given refers to (3S-(3alpha(2E,7S,11S),4beta,21beta))-isomer	2.83	3	0
neopterin [no description available]	2.11	1	0
rifampin Rifampin: A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)	3.56	2	0	cyclic ketal; hydrazone; N-iminopiperazine; N-methylpiperazine; rifamycins; semisynthetic derivative; zwitterion	angiogenesis inhibitor; antiamoebic agent; antineoplastic agent; antitubercular agent; DNA synthesis inhibitor; EC 2.7.7.6 (RNA polymerase) inhibitor; Escherichia coli metabolite; geroprotector; leprostatic drug; neuroprotective agent; pregnane X receptor agonist; protein synthesis inhibitor
clozapine Clozapine: A tricylic dibenzodiazepine, classified as an atypical antipsychotic agent. It binds several types of central nervous system receptors, and displays a unique pharmacological profile. Clozapine is a serotonin antagonist, with strong binding to 5-HT 2A/2C receptor subtype. It also displays strong affinity to several dopaminergic receptors, but shows only weak antagonism at the dopamine D2 receptor, a receptor commonly thought to modulate neuroleptic activity. Agranulocytosis is a major adverse effect associated with administration of this agent.. clozapine : A benzodiazepine that is 5H-dibenzo[b,e][1,4]diazepine substituted by a chloro group at position 8 and a 4-methylpiperazin-1-yl group at position 11. It is a second generation antipsychotic used in the treatment of psychiatric disorders like schizophrenia.	3.54	2	0	benzodiazepine; N-arylpiperazine; N-methylpiperazine; organochlorine compound	adrenergic antagonist; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; environmental contaminant; GABA antagonist; histamine antagonist; muscarinic antagonist; second generation antipsychotic; serotonergic antagonist; xenobiotic
olanzapine Olanzapine: A benzodiazepine derivative that binds SEROTONIN RECEPTORS; MUSCARINIC RECEPTORS; HISTAMINE H1 RECEPTORS; ADRENERGIC ALPHA-1 RECEPTORS; and DOPAMINE RECEPTORS. It is an antipsychotic agent used in the treatment of SCHIZOPHRENIA; BIPOLAR DISORDER; and MAJOR DEPRESSIVE DISORDER; it may also reduce nausea and vomiting in patients undergoing chemotherapy.. olanzapine : A benzodiazepine that is 10H-thieno[2,3-b][1,5]benzodiazepine substituted by a methyl group at position 2 and a 4-methylpiperazin-1-yl group at position 4.	2.1	1	0	benzodiazepine; N-arylpiperazine; N-methylpiperazine	antiemetic; dopaminergic antagonist; histamine antagonist; muscarinic antagonist; second generation antipsychotic; serotonergic antagonist; serotonin uptake inhibitor
zaprinast zaprinast: anaphylaxis inhibitor; structure	1.97	1	0	triazolopyrimidines
allopurinol Allopurinol: A XANTHINE OXIDASE inhibitor that decreases URIC ACID production. It also acts as an antimetabolite on some simpler organisms.. allopurinol : A bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring.	4.23	17	0	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger
2,2'-(hydroxynitrosohydrazono)bis-ethanamine 2,2'-(hydroxynitrosohydrazono)bis-ethanamine: a nitric oxide (NO) generating compound. 1,1-bis(2-aminoethyl)-2-hydroxy-3-oxotriazane : A nitroso compound that is triazane in which the the nitrogen at position 1 is substituted by two 2-aminoethyl groups, that at position 2 is substituted by a hydroxy group, and that at position 3 is substituted by an oxo group.	2.03	1	0
3,4,5-trihydroxybenzamidoxime 3,4,5-trihydroxybenzamidoxime: structure given in first source	2.03	1	0	benzenetriol
norclozapine norclozapine: structure given in first source. N-desmethylclozapine : A dibenzodoazepine substituted with chloro and piperazino groups which is a major metabolite of clozapine; a potent and selective 5-HT2C serotonin receptor antagonist.	3.54	2	0	dibenzodiazepine; organochlorine compound; piperazines	delta-opioid receptor agonist; metabolite; serotonergic antagonist
guanosine 5'-o-(2-thiodiphosphate) [no description available]	1.98	1	0	nucleoside diphosphate analogue
5,6,7,8-tetrahydrofolic acid 5,6,7,8-tetrahydrofolic acid: RN given refers to (DL)-isomer	2.42	2	0	tetrahydrofolic acid
8-bromocyclic gmp 8-bromo-3',5'-cyclic GMP : A 3',5'-cyclic purine nucleotide that is 3',5'-cyclic GMP bearing an additional bromo substituent at position 8 on the guanine ring. A membrane permeable cGMP analogue that activates protein kinase G (PKG). It is 4.3-fold more potent than cGMP in activating PKG1alpha and promotes relaxation of tracheal and vascular smooth muscle tissue in vitro.	2.38	2	0	3',5'-cyclic purine nucleotide; organobromine compound	muscle relaxant; protein kinase G agonist
nataxazole nataxazole: has antineoplastic activity; isolated from Streptomyces; structure in first source	2.17	1	0
methylnitronitrosoguanidine Methylnitronitrosoguanidine: A nitrosoguanidine derivative with potent mutagenic and carcinogenic properties.. N-methyl-N'-nitro-N-nitrosoguanidine : An N-nitroguanidine compound having nitroso and methyl substituents at the N'-position	3.09	5	0	nitroso compound	alkylating agent
8-hydroxy-2'-deoxyguanosine 8-Hydroxy-2'-Deoxyguanosine: Common oxidized form of deoxyguanosine in which C-8 position of guanine base has a carbonyl group.. 8-hydroxy-2'-deoxyguanosine : Guanosine substituted at the purine 8-position by a hydroxy group. It is used as a biomarker of oxidative DNA damage.	7.42	2	0	guanosines	biomarker
antipyrylazo iii antipyrylazo III: a metallochromic indicator	1.97	1	0
5-methyltetrahydrofolate 5-methyltetrahydrofolate : A group of heterocyclic compounds based on the 5-methyl-5,6,7,8-tetrahydropteroic acid skeleton conjugated with one or more L-glutamic acid or L-glutamate units.	2.41	1	0
2',4'-dichlorobenzamil amiloride [no description available]	1.98	1	0
defibrotide defibrotide: Single-stranded polydeoxyribonucleotide extracted from mammalian organs and used in the treatment of HEPATIC VENO-OCCLUSIVE DISEASE in patients with kidney or lung abnormalities following HEMATOPOIETIC STEM CELL TRANSPLANTATION	1.99	1	0
dibutyryl cyclic gmp Dibutyryl Cyclic GMP: N-(1-Oxobutyl)-cyclic 3',5'-(hydrogen phosphate)-2'-butanoate guanosine. A derivative of cyclic GMP. It has a higher resistance to extracellular and intracellular phosphodiesterase than cyclic GMP.	1.97	1	0
maltodextrin maltodextrin : A dextrin in which the D-glucose units are linked by alpha-(1->4) glycosidic bonds.	2.13	1	0
concanavalin a Concanavalin A: A MANNOSE/GLUCOSE binding lectin isolated from the jack bean (Canavalia ensiformis). It is a potent mitogen used to stimulate cell proliferation in lymphocytes, primarily T-lymphocyte, cultures.	3.93	13	0
metallothionein Metallothionein: A low-molecular-weight (approx. 10 kD) protein occurring in the cytoplasm of kidney cortex and liver. It is rich in cysteinyl residues and contains no aromatic amino acids. Metallothionein shows high affinity for bivalent heavy metals.	1.98	1	0
vescalagin vescalagin: structure in first source; castalagin is the (33beta)-isomer of vescalagin	2.69	2	0
leptin Leptin: A 16-kDa peptide hormone secreted from WHITE ADIPOCYTES. Leptin serves as a feedback signal from fat cells to the CENTRAL NERVOUS SYSTEM in regulation of food intake, energy balance, and fat storage.	8.21	5	0
tetrafluoroaluminate tetrafluoroaluminate: induces inositol phosphate formation	2.07	1	0
phenanthrenes Phenanthrenes: POLYCYCLIC AROMATIC HYDROCARBONS composed of three fused BENZENE rings.. phenanthrenes : Any benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof.	2.31	1	0

Condition	Relationship Strength	Studies	Trials
Bilirubinemia [description not available]	2.92	1	0
Benign Neoplasms [description not available]	9.83	51	1
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	9.83	51	1
Adenocarcinoma, Basal Cell [description not available]	5.11	16	0
Breast Cancer [description not available]	5.86	34	0
Cancer of Cervix [description not available]	3.88	11	0
Leukemia, Lymphocytic [description not available]	2.01	1	0
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	10.11	16	0
Breast Neoplasms Tumors or cancer of the human BREAST.	5.86	34	0
Uterine Cervical Neoplasms Tumors or cancer of the UTERINE CERVIX.	3.88	11	0
Leukemia, Lymphoid Leukemia associated with HYPERPLASIA of the lymphoid tissues and increased numbers of circulating malignant LYMPHOCYTES and lymphoblasts.	2.01	1	0
Diabetes Mellitus A heterogeneous group of disorders characterized by HYPERGLYCEMIA and GLUCOSE INTOLERANCE.	5.37	9	0
Leucocythaemia [description not available]	4.42	7	0
Leukemia L 1210 [description not available]	2.04	1	0
Leukemia A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)	4.42	7	0
Complications of Diabetes Mellitus [description not available]	2.96	4	0
Cataract, Membranous [description not available]	3.01	4	0
Cataract Partial or complete opacity on or in the lens or capsule of one or both eyes, impairing vision or causing blindness. The many kinds of cataract are classified by their morphology (size, shape, location) or etiology (cause and time of occurrence). (Dorland, 27th ed)	8.01	4	0
Endotoxin Shock [description not available]	3.32	6	0
Shock, Septic Sepsis associated with HYPOTENSION or hypoperfusion despite adequate fluid resuscitation. Perfusion abnormalities may include but are not limited to LACTIC ACIDOSIS; OLIGURIA; or acute alteration in mental status.	3.32	6	0
Cancer of Colon [description not available]	7.74	22	1
Colonic Neoplasms Tumors or cancer of the COLON.	7.74	22	1
Encephalitis, Polio [description not available]	2.06	1	0
Poliomyelitis An acute infectious disease of humans, particularly children, caused by any of three serotypes of human poliovirus (POLIOVIRUS). Usually the infection is limited to the gastrointestinal tract and nasopharynx, and is often asymptomatic. The central nervous system, primarily the spinal cord, may be affected, leading to rapidly progressive paralysis, coarse FASCICULATION and hyporeflexia. Motor neurons are primarily affected. Encephalitis may also occur. The virus replicates in the nervous system, and may cause significant neuronal loss, most notably in the spinal cord. A rare related condition, nonpoliovirus poliomyelitis, may result from infections with nonpoliovirus enteroviruses. (From Adams et al., Principles of Neurology, 6th ed, pp764-5)	2.06	1	0
Obesity A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).	8.21	33	1
Acute Confusional Senile Dementia [description not available]	4.79	28	0
Alzheimer Disease A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)	4.79	28	0
Angiogenesis, Pathologic [description not available]	5.01	8	0
Degenerative Diseases, Central Nervous System [description not available]	5.47	9	0
Neurodegenerative Diseases Hereditary and sporadic conditions which are characterized by progressive nervous system dysfunction. These disorders are often associated with atrophy of the affected central or peripheral nervous system structures.	5.47	9	0
Protein Aggregation, Pathological A biochemical phenomenon in which misfolded proteins aggregate either intra- or extracellularly. Triggered by factors such as MUTATION; POST-TRANSLATIONAL MODIFICATIONS, and environmental stress, it is generally associated with ALZHEIMER DISEASE; PARKINSON DISEASE; HUNTINGTON DISEASE; and TYPE 2 DIABETES MELLITUS.	3.11	4	0
HIV Human immunodeficiency virus. A non-taxonomic and historical term referring to any of two species, specifically HIV-1 and/or HIV-2. Prior to 1986, this was called human T-lymphotropic virus type III/lymphadenopathy-associated virus (HTLV-III/LAV). From 1986-1990, it was an official species called HIV. Since 1991, HIV was no longer considered an official species name; the two species were designated HIV-1 and HIV-2.	2.11	1	0
Adjuvant Arthritis [description not available]	3.87	10	0
Anemia, Fanconi [description not available]	2.13	1	0
Fanconi Anemia Congenital disorder affecting all bone marrow elements, resulting in ANEMIA; LEUKOPENIA; and THROMBOPENIA, and associated with cardiac, renal, and limb malformations as well as dermal pigmentary changes. Spontaneous CHROMOSOME BREAKAGE is a feature of this disease along with predisposition to LEUKEMIA. There are at least 7 complementation groups in Fanconi anemia: FANCA, FANCB, FANCC, FANCD1, FANCD2, FANCE, FANCF, FANCG, and FANCL. (from Online Mendelian Inheritance in Man, http://www.ncbi.nlm.nih.gov/entrez/dispomim.cgi?id=227650, August 20, 2004)	2.13	1	0
Carcinoma, Non-Small Cell Lung [description not available]	3.73	9	0
Cancer of Lung [description not available]	4.85	31	0
Carcinoma, Non-Small-Cell Lung A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.	3.73	9	0
Lung Neoplasms Tumors or cancer of the LUNG.	4.85	31	0
Diabetes Mellitus, Adult-Onset [description not available]	7.29	20	1
Diabetes Mellitus, Type 2 A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.	7.29	20	1
Extravascular Hemolysis [description not available]	4.63	25	0
Hemolysis The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.	9.63	25	0
Tauopathies Neurodegenerative disorders involving deposition of abnormal tau protein isoforms (TAU PROTEINS) in neurons and glial cells in the brain. Pathological aggregations of tau proteins are associated with mutation of the tau gene on chromosome 17 in patients with ALZHEIMER DISEASE; DEMENTIA; PARKINSONIAN DISORDERS; progressive supranuclear palsy (SUPRANUCLEAR PALSY, PROGRESSIVE); and corticobasal degeneration.	2.72	2	0
Carcinogenesis The origin, production or development of cancer through genotypic and phenotypic changes which upset the normal balance between cell proliferation and cell death. Carcinogenesis generally requires a constellation of steps, which may occur quickly or over a period of many years.	2.63	2	0
Colorectal Cancer [description not available]	5.18	15	0
Colorectal Neoplasms Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.	5.18	15	0
Congenital Zika Syndrome [description not available]	2.76	2	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	9.9	119	1
Zika Virus Infection A viral disease transmitted by the bite of AEDES mosquitoes infected with ZIKA VIRUS. Its mild DENGUE-like symptoms include fever, rash, headaches and ARTHRALGIA. The viral infection during pregnancy, in rare cases, is associated with congenital brain and ocular abnormalities, called Congenital Zika Syndrome, including MICROCEPHALY and may also lead to GUILLAIN-BARRE SYNDROME.	2.76	2	0
2019 Novel Coronavirus Disease [description not available]	4.96	9	0
Chronic Lung Injury [description not available]	2.69	2	0
Grippe [description not available]	2.9	2	0
Infections, Orthomyxoviridae [description not available]	2.75	3	0
Experimental Lung Inflammation Inflammation of any part, segment or lobe, of the lung parenchyma.	2.59	2	0
Influenza, Human An acute viral infection in humans involving the respiratory tract. It is marked by inflammation of the NASAL MUCOSA; the PHARYNX; and conjunctiva, and by headache and severe, often generalized, myalgia.	2.9	2	0
Orthomyxoviridae Infections Virus diseases caused by the ORTHOMYXOVIRIDAE.	2.75	3	0
Pneumonia Infection of the lung often accompanied by inflammation.	2.59	2	0
Innate Inflammatory Response [description not available]	8.59	71	0
Arthritis, Degenerative [description not available]	3.88	10	0
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	8.59	71	0
Osteoarthritis A progressive, degenerative joint disease, the most common form of arthritis, especially in older persons. The disease is thought to result not from the aging process but from biochemical changes and biomechanical stresses affecting articular cartilage. In the foreign literature it is often called osteoarthrosis deformans.	3.88	10	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	12.02	41	2
Alloxan Diabetes [description not available]	6.05	40	0
Eye Disorders [description not available]	7.31	1	0
Eye Diseases Diseases affecting the eye.	2.31	1	0
Urinary Lithiasis [description not available]	2.82	2	0
Kidney Stones [description not available]	2.66	2	0
Kidney Calculi Stones in the KIDNEY, usually formed in the urine-collecting area of the kidney (KIDNEY PELVIS). Their sizes vary and most contains CALCIUM OXALATE.	2.66	2	0
Urolithiasis Formation of stones in any part of the URINARY TRACT, usually in the KIDNEY; URINARY BLADDER; or the URETER.	7.82	2	0
Colitis Gravis [description not available]	3.59	7	0
Colitis, Ulcerative Inflammation of the COLON that is predominantly confined to the MUCOSA. Its major symptoms include DIARRHEA, rectal BLEEDING, the passage of MUCUS, and ABDOMINAL PAIN.	3.59	7	0
Kidney Failure A severe irreversible decline in the ability of kidneys to remove wastes, concentrate URINE, and maintain ELECTROLYTE BALANCE; BLOOD PRESSURE; and CALCIUM metabolism.	2.31	1	0
Renal Insufficiency Conditions in which the KIDNEYS perform below the normal level in the ability to remove wastes, concentrate URINE, and maintain ELECTROLYTE BALANCE; BLOOD PRESSURE; and CALCIUM metabolism. Renal insufficiency can be classified by the degree of kidney damage (as measured by the level of PROTEINURIA) and reduction in GLOMERULAR FILTRATION RATE.	2.31	1	0
Blood Poisoning [description not available]	2.88	3	0
Sepsis Systemic inflammatory response syndrome with a proven or suspected infectious etiology. When sepsis is associated with organ dysfunction distant from the site of infection, it is called severe sepsis. When sepsis is accompanied by HYPOTENSION despite adequate fluid infusion, it is called SEPTIC SHOCK.	7.88	3	0
Encephalopathy, Hepatic [description not available]	2.9	2	0
Hepatic Encephalopathy A syndrome characterized by central nervous system dysfunction in association with LIVER FAILURE, including portal-systemic shunts. Clinical features include lethargy and CONFUSION (frequently progressing to COMA); ASTERIXIS; NYSTAGMUS, PATHOLOGIC; brisk oculovestibular reflexes; decorticate and decerebrate posturing; MUSCLE SPASTICITY; and bilateral extensor plantar reflexes (see REFLEX, BABINSKI). ELECTROENCEPHALOGRAPHY may demonstrate triphasic waves. (From Adams et al., Principles of Neurology, 6th ed, pp1117-20; Plum & Posner, Diagnosis of Stupor and Coma, 3rd ed, p222-5)	7.9	2	0
Hyperglycemia, Postprandial Abnormally high BLOOD GLUCOSE level after a meal.	4.99	13	0
Insulin Sensitivity [description not available]	13.04	10	1
Hyperglycemia Abnormally high BLOOD GLUCOSE level.	4.99	13	0
Insulin Resistance Diminished effectiveness of INSULIN in lowering blood sugar levels: requiring the use of 200 units or more of insulin per day to prevent HYPERGLYCEMIA or KETOSIS.	13.04	10	1
Menopause The last menstrual period. Permanent cessation of menses (MENSTRUATION) is usually defined after 6 to 12 months of AMENORRHEA in a woman over 45 years of age. In the United States, menopause generally occurs in women between 48 and 55 years of age.	2.41	1	0
Acute Kidney Failure [description not available]	3.8	9	0
Acute Kidney Injury Abrupt reduction in kidney function. Acute kidney injury encompasses the entire spectrum of the syndrome including acute kidney failure; ACUTE KIDNEY TUBULAR NECROSIS; and other less severe conditions.	8.8	9	0
Rheumatoid Arthritis [description not available]	3.46	6	0
Arthritis, Rheumatoid A chronic systemic disease, primarily of the joints, marked by inflammatory changes in the synovial membranes and articular structures, widespread fibrinoid degeneration of the collagen fibers in mesenchymal tissues, and by atrophy and rarefaction of bony structures. Etiology is unknown, but autoimmune mechanisms have been implicated.	3.46	6	0
Acute Ischemic Stroke [description not available]	5.58	4	1
Cerebral Ischemia [description not available]	6.43	14	1
Ischemic Stroke Stroke due to BRAIN ISCHEMIA resulting in interruption or reduction of blood flow to a part of the brain. When obstruction is due to a BLOOD CLOT formed within in a cerebral blood vessel it is a thrombotic stroke. When obstruction is formed elsewhere and moved to block a cerebral blood vessel (see CEREBRAL EMBOLISM) it is referred to as embolic stroke. Wake-up stroke refers to ischemic stroke occurring during sleep while cryptogenic stroke refers to ischemic stroke of unknown origin.	10.58	4	1
Brain Ischemia Localized reduction of blood flow to brain tissue due to arterial obstruction or systemic hypoperfusion. This frequently occurs in conjunction with brain hypoxia (HYPOXIA, BRAIN). Prolonged ischemia is associated with BRAIN INFARCTION.	6.43	14	1
Left Ventricular Hypertrophy [description not available]	2.66	2	0
Cardiac Hypertrophy Enlargement of the HEART due to chamber HYPERTROPHY, an increase in wall thickness without an increase in the number of cells (MYOCYTES, CARDIAC). It is the result of increase in myocyte size, mitochondrial and myofibrillar mass, as well as changes in extracellular matrix.	3.74	8	0
Cardiomegaly Enlargement of the HEART, usually indicated by a cardiothoracic ratio above 0.50. Heart enlargement may involve the right, the left, or both HEART VENTRICLES or HEART ATRIA. Cardiomegaly is a nonspecific symptom seen in patients with chronic systolic heart failure (HEART FAILURE) or several forms of CARDIOMYOPATHIES.	3.74	8	0
Hypertrophy, Left Ventricular Enlargement of the LEFT VENTRICLE of the heart. This increase in ventricular mass is attributed to sustained abnormal pressure or volume loads and is a contributor to cardiovascular morbidity and mortality.	2.66	2	0
Acute Liver Injury, Drug-Induced [description not available]	4.96	36	0
Iron Overload An excessive accumulation of iron in the body due to a greater than normal absorption of iron from the gastrointestinal tract or from parenteral injection. This may arise from idiopathic hemochromatosis, excessive iron intake, chronic alcoholism, certain types of refractory anemia, or transfusional hemosiderosis. (From Churchill's Illustrated Medical Dictionary, 1989)	8.04	3	0
Chemical and Drug Induced Liver Injury A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.	4.96	36	0
Bowel Diseases, Inflammatory [description not available]	2.94	3	0
Inflammatory Bowel Diseases Chronic, non-specific inflammation of the GASTROINTESTINAL TRACT. Etiology may be genetic or environmental. This term includes CROHN DISEASE and ULCERATIVE COLITIS.	2.94	3	0
Cerebral Infarction, Middle Cerebral Artery [description not available]	4.45	4	1
Apoplexy [description not available]	5.04	8	1
Infarction, Middle Cerebral Artery NECROSIS occurring in the MIDDLE CEREBRAL ARTERY distribution system which brings blood to the entire lateral aspects of each CEREBRAL HEMISPHERE. Clinical signs include impaired cognition; APHASIA; AGRAPHIA; weak and numbness in the face and arms, contralaterally or bilaterally depending on the infarction.	4.45	4	1
Stroke A group of pathological conditions characterized by sudden, non-convulsive loss of neurological function due to BRAIN ISCHEMIA or INTRACRANIAL HEMORRHAGES. Stroke is classified by the type of tissue NECROSIS, such as the anatomic location, vasculature involved, etiology, age of the affected individual, and hemorrhagic vs. non-hemorrhagic nature. (From Adams et al., Principles of Neurology, 6th ed, pp777-810)	10.04	8	1
Pleurisy INFLAMMATION of PLEURA, the lining of the LUNG. When PARIETAL PLEURA is involved, there is pleuritic CHEST PAIN.	2.59	2	0
Autism [description not available]	2.41	1	0
Age-Related Memory Disorders [description not available]	3.17	5	0
Autistic Disorder A disorder beginning in childhood. It is marked by the presence of markedly abnormal or impaired development in social interaction and communication and a markedly restricted repertoire of activity and interest. Manifestations of the disorder vary greatly depending on the developmental level and chronological age of the individual. (DSM-V)	2.41	1	0
Memory Disorders Disturbances in registering an impression, in the retention of an acquired impression, or in the recall of an impression. Memory impairments are associated with DEMENTIA; CRANIOCEREBRAL TRAUMA; ENCEPHALITIS; ALCOHOLISM (see also ALCOHOL AMNESTIC DISORDER); SCHIZOPHRENIA; and other conditions.	3.17	5	0
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	4.88	13	0
Endometrioma An enlarged area of ENDOMETRIOSIS that resembles a tumor. It is usually found in the OVARY. When it is filled with old blood, it is known as a chocolate cyst.	2.96	3	0
Endometriosis A condition in which functional endometrial tissue is present outside the UTERUS. It is often confined to the PELVIS involving the OVARY, the ligaments, cul-de-sac, and the uterovesical peritoneum.	2.96	3	0
B-Cell Chronic Lymphocytic Leukemia [description not available]	2.41	1	0
Leukemia, Lymphocytic, Chronic, B-Cell A chronic leukemia characterized by abnormal B-lymphocytes and often generalized lymphadenopathy. In patients presenting predominately with blood and bone marrow involvement it is called chronic lymphocytic leukemia (CLL); in those predominately with enlarged lymph nodes it is called small lymphocytic lymphoma. These terms represent spectrums of the same disease.	2.41	1	0
Palmoplantaris Pustulosis [description not available]	3.69	6	0
Psoriasis A common genetically determined, chronic, inflammatory skin disease characterized by rounded erythematous, dry, scaling patches. The lesions have a predilection for nails, scalp, genitalia, extensor surfaces, and the lumbosacral region. Accelerated epidermopoiesis is considered to be the fundamental pathologic feature in psoriasis.	3.69	6	0
Plica Syndrome [description not available]	2.41	1	0
Gout Metabolic disorder characterized by recurrent acute arthritis, hyperuricemia and deposition of sodium urate in and around the joints, sometimes with formation of URIC ACID calculi.	2.53	2	0
Synovitis Inflammation of the SYNOVIAL MEMBRANE.	7.41	1	0
Chemical and Drug Induced Liver Injury, Chronic Liver disease lasting six months or more, caused by an adverse effect of a drug or chemical. The adverse effect may be caused by drugs, drug metabolites, chemicals from the environment, or an idiosyncratic response.	2.53	2	0
Aspergillus Infection [description not available]	2.93	3	0
Eye Infections, Fungal Infection by a variety of fungi, usually through four possible mechanisms: superficial infection producing conjunctivitis, keratitis, or lacrimal obstruction; extension of infection from neighboring structures - skin, paranasal sinuses, nasopharynx; direct introduction during surgery or accidental penetrating trauma; or via the blood or lymphatic routes in patients with underlying mycoses.	2.82	2	0
Aspergillosis Infections with fungi of the genus ASPERGILLUS.	2.93	3	0
Keratitis Inflammation of the cornea.	3.07	3	0
Atherogenesis [description not available]	5.07	14	0
Cardiovascular Diseases Pathological conditions involving the CARDIOVASCULAR SYSTEM including the HEART; the BLOOD VESSELS; or the PERICARDIUM.	6.68	6	2
Atherosclerosis A thickening and loss of elasticity of the walls of ARTERIES that occurs with formation of ATHEROSCLEROTIC PLAQUES within the ARTERIAL INTIMA.	5.07	14	0
Age-Related Osteoporosis [description not available]	3.69	8	0
Osteoporosis Reduction of bone mass without alteration in the composition of bone, leading to fractures. Primary osteoporosis can be of two major types: postmenopausal osteoporosis (OSTEOPOROSIS, POSTMENOPAUSAL) and age-related or senile osteoporosis.	3.69	8	0
Depression Depressive states usually of moderate intensity in contrast with MAJOR DEPRESSIVE DISORDER present in neurotic and psychotic disorders.	5.35	12	1
Cirrhosis [description not available]	4.03	12	0
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	4.03	12	0
Rhabdomyolysis Necrosis or disintegration of skeletal muscle often followed by myoglobinuria.	7.41	1	0
Carcinoma, Epidermoid [description not available]	4.26	17	0
Hepatocellular Carcinoma [description not available]	4.13	15	0
Cancer of Liver [description not available]	4.34	19	0
Cancer of the Tongue [description not available]	2.93	3	0
Carcinoma, Squamous Cell A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed)	4.26	17	0
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	4.13	15	0
Liver Neoplasms Tumors or cancer of the LIVER.	4.34	19	0
Tongue Neoplasms Tumors or cancer of the TONGUE.	2.93	3	0
Infection, Wound [description not available]	2.89	3	0
HIV Coinfection [description not available]	3.07	4	0
HIV Infections Includes the spectrum of human immunodeficiency virus infections that range from asymptomatic seropositivity, thru AIDS-related complex (ARC), to acquired immunodeficiency syndrome (AIDS).	3.07	4	0
E coli Infections [description not available]	2.41	1	0
Infections, Staphylococcal [description not available]	5.15	16	0
Escherichia coli Infections Infections with bacteria of the species ESCHERICHIA COLI.	2.41	1	0
Staphylococcal Infections Infections with bacteria of the genus STAPHYLOCOCCUS.	5.15	16	0
Anasarca [description not available]	4.36	19	0
Bleeding [description not available]	5.24	7	0
Envenomation, Snakebite [description not available]	2.54	2	0
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	9.36	19	0
Hemorrhage Bleeding or escape of blood from a vessel.	10.24	7	0
Fasting Hypoglycemia HYPOGLYCEMIA expressed in the postabsorptive state, after prolonged FASTING, or an overnight fast.	2.54	2	0
Hypoglycemia A syndrome of abnormally low BLOOD GLUCOSE level. Clinical hypoglycemia has diverse etiologies. Severe hypoglycemia eventually lead to glucose deprivation of the CENTRAL NERVOUS SYSTEM resulting in HUNGER; SWEATING; PARESTHESIA; impaired mental function; SEIZURES; COMA; and even DEATH.	2.54	2	0
Chronic Hepatitis B [description not available]	2.41	1	0
Hepatitis B Virus Infection [description not available]	2.41	1	0
Hepatitis B INFLAMMATION of the LIVER in humans caused by a member of the ORTHOHEPADNAVIRUS genus, HEPATITIS B VIRUS. It is primarily transmitted by parenteral exposure, such as transfusion of contaminated blood or blood products, but can also be transmitted via sexual or intimate personal contact.	2.41	1	0
Hepatitis B, Chronic INFLAMMATION of the LIVER in humans caused by HEPATITIS B VIRUS lasting six months or more. It is primarily transmitted by parenteral exposure, such as transfusion of contaminated blood or blood products, but can also be transmitted via sexual or intimate personal contact.	2.41	1	0
Atheroma [description not available]	3.13	4	0
Epithelial Ovarian Cancer [description not available]	2.41	1	0
Cancer of Ovary [description not available]	3.84	9	0
Carcinoma, Ovarian Epithelial A malignant neoplasm that originates in cells on the surface EPITHELIUM of the ovary and is the most common form of ovarian cancer. There are five histologic subtypes: papillary serous, endometrioid, mucinous, clear cell, and transitional cell. Mutations in BRCA1, OPCML, PRKN, PIK3CA, AKT1, CTNNB1, RRAS2, and CDH1 genes are associated with this cancer.	2.41	1	0
Ovarian Neoplasms Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.	3.84	9	0
Injury, Ischemia-Reperfusion [description not available]	3.99	12	0
Ischemia A hypoperfusion of the BLOOD through an organ or tissue caused by a PATHOLOGIC CONSTRICTION or obstruction of its BLOOD VESSELS, or an absence of BLOOD CIRCULATION.	2.76	3	0
Reperfusion Injury Adverse functional, metabolic, or structural changes in tissues that result from the restoration of blood flow to the tissue (REPERFUSION) following ISCHEMIA.	8.99	12	0
Nephrolithiasis Formation of stones in the KIDNEY.	2.41	1	0
Hyperuricemia Excessive URIC ACID or urate in blood as defined by its solubility in plasma at 37 degrees C; greater than 0.42mmol per liter (7.0mg/dL) in men or 0.36mmol per liter (6.0mg/dL) in women. This condition is caused by overproduction of uric acid or impaired renal clearance. Hyperuricemia can be acquired, drug-induced or genetically determined (LESCH-NYHAN SYNDROME). It is associated with HYPERTENSION and GOUT.	2.53	2	0
Dermatitis Any inflammation of the skin.	2.41	1	0
Osteogenic Sarcoma [description not available]	2.97	4	0
Osteosarcoma A sarcoma originating in bone-forming cells, affecting the ends of long bones. It is the most common and most malignant of sarcomas of the bones, and occurs chiefly among 10- to 25-year-old youths. (From Stedman, 25th ed)	7.97	4	0
Blood Clot [description not available]	2.41	1	0
Thrombosis Formation and development of a thrombus or blood clot in the blood vessel.	2.41	1	0
Infections, Nematode [description not available]	2.69	2	0
Caprine Diseases [description not available]	2.41	1	0
Haemonchiasis Infection with nematodes of the genus HAEMONCHUS, characterized by digestive abnormalities and anemia similar to that from hookworm infestation.	2.41	1	0
Benign Neoplasms, Brain [description not available]	3.47	7	0
Astrocytoma, Grade IV [description not available]	3.49	7	0
Glial Cell Tumors [description not available]	3.68	9	0
Brain Neoplasms Neoplasms of the intracranial components of the central nervous system, including the cerebral hemispheres, basal ganglia, hypothalamus, thalamus, brain stem, and cerebellum. Brain neoplasms are subdivided into primary (originating from brain tissue) and secondary (i.e., metastatic) forms. Primary neoplasms are subdivided into benign and malignant forms. In general, brain tumors may also be classified by age of onset, histologic type, or presenting location in the brain.	3.47	7	0
Glioblastoma A malignant form of astrocytoma histologically characterized by pleomorphism of cells, nuclear atypia, microhemorrhage, and necrosis. They may arise in any region of the central nervous system, with a predilection for the cerebral hemispheres, basal ganglia, and commissural pathways. Clinical presentation most frequently occurs in the fifth or sixth decade of life with focal neurologic signs or seizures.	3.49	7	0
Glioma Benign and malignant central nervous system neoplasms derived from glial cells (i.e., astrocytes, oligodendrocytes, and ependymocytes). Astrocytes may give rise to astrocytomas (ASTROCYTOMA) or glioblastoma multiforme (see GLIOBLASTOMA). Oligodendrocytes give rise to oligodendrogliomas (OLIGODENDROGLIOMA) and ependymocytes may undergo transformation to become EPENDYMOMA; CHOROID PLEXUS NEOPLASMS; or colloid cysts of the third ventricle. (From Escourolle et al., Manual of Basic Neuropathology, 2nd ed, p21)	3.68	9	0
Cardiac Rupture, Traumatic [description not available]	2.41	1	0
Hyperthyroid [description not available]	7.6	1	0
Central Hypothyroidism [description not available]	2.82	2	0
Hyperthyroidism Hypersecretion of THYROID HORMONES from the THYROID GLAND. Elevated levels of thyroid hormones increase BASAL METABOLIC RATE.	7.6	1	0
Hypothyroidism A syndrome that results from abnormally low secretion of THYROID HORMONES from the THYROID GLAND, leading to a decrease in BASAL METABOLIC RATE. In its most severe form, there is accumulation of MUCOPOLYSACCHARIDES in the SKIN and EDEMA, known as MYXEDEMA. It may be primary or secondary due to other pituitary disease, or hypothalamic dysfunction.	2.82	2	0
Condition, Preneoplastic [description not available]	2.6	1	0
Cancer of Stomach [description not available]	3.33	6	0
Cough A sudden, audible expulsion of air from the lungs through a partially closed glottis, preceded by inhalation. It is a protective response that serves to clear the trachea, bronchi, and/or lungs of irritants and secretions, or to prevent aspiration of foreign materials into the lungs.	2.6	1	0
Precancerous Conditions Pathological conditions that tend eventually to become malignant.	2.6	1	0
Stomach Neoplasms Tumors or cancer of the STOMACH.	3.33	6	0
Carcinoma, Basal Cell, Pigmented [description not available]	2.6	1	0
Cancer of Skin [description not available]	3.96	13	0
Carcinoma, Basal Cell A malignant skin neoplasm that seldom metastasizes but has potentialities for local invasion and destruction. Clinically it is divided into types: nodular, cicatricial, morphaic, and erythematoid (pagetoid). They develop on hair-bearing skin, most commonly on sun-exposed areas. Approximately 85% are found on the head and neck area and the remaining 15% on the trunk and limbs. (From DeVita Jr et al., Cancer: Principles & Practice of Oncology, 3d ed, p1471)	2.6	1	0
Skin Neoplasms Tumors or cancer of the SKIN.	3.96	13	0
Liver Dysfunction [description not available]	4.17	15	0
Liver Diseases Pathological processes of the LIVER.	4.17	15	0
Fatty Liver, Nonalcoholic [description not available]	3.9	9	0
Non-alcoholic Fatty Liver Disease Fatty liver finding without excessive ALCOHOL CONSUMPTION.	8.9	9	0
Allergic Encephalomyelitis [description not available]	2.94	3	0
Vascular Diseases Pathological processes involving any of the BLOOD VESSELS in the cardiac or peripheral circulation. They include diseases of ARTERIES; VEINS; and rest of the vasculature system in the body.	2.6	1	0
Idiopathic Parkinson Disease [description not available]	2.89	3	0
Parkinson Disease A progressive, degenerative neurologic disease characterized by a TREMOR that is maximal at rest, retropulsion (i.e. a tendency to fall backwards), rigidity, stooped posture, slowness of voluntary movements, and a masklike facial expression. Pathologic features include loss of melanin containing neurons in the substantia nigra and other pigmented nuclei of the brainstem. LEWY BODIES are present in the substantia nigra and locus coeruleus but may also be found in a related condition (LEWY BODY DISEASE, DIFFUSE) characterized by dementia in combination with varying degrees of parkinsonism. (Adams et al., Principles of Neurology, 6th ed, p1059, pp1067-75)	2.89	3	0
Pain, Chronic [description not available]	2.6	1	0
Nerve Pain [description not available]	2.6	1	0
Neuralgia Intense or aching pain that occurs along the course or distribution of a peripheral or cranial nerve.	2.6	1	0
Chronic Pain Aching sensation that persists for more than a few months. It may or may not be associated with trauma or disease, and may persist after the initial injury has healed. Its localization, character, and timing are more vague than with acute pain.	7.6	1	0
Cholangiocellular Carcinoma [description not available]	2.87	3	0
Bile Duct Cancer [description not available]	2.87	3	0
Bile Duct Neoplasms Tumors or cancer of the BILE DUCTS.	2.87	3	0
Cholangiocarcinoma A malignant tumor arising from the epithelium of the BILE DUCTS.	2.87	3	0
Chronic Encephalopathy, Post-Concussive [description not available]	2.6	1	0
Chronic Traumatic Encephalopathy Degenerative brain disease linked to repetitive brain trauma. Progressive symptoms may include MEMORY LOSS; AGGRESSION; or DEPRESSION.	7.6	1	0
Aberrant Crypt Foci Clusters of colonic crypts that appear different from the surrounding mucosa when visualized after staining. They are of interest as putative precursors to colorectal adenomas and potential biomarkers for colorectal carcinoma.	2.6	1	0
Animal Mammary Carcinoma [description not available]	2.6	1	0
Burns Injuries to tissues caused by contact with heat, steam, chemicals (BURNS, CHEMICAL), electricity (BURNS, ELECTRIC), or the like.	2.95	4	0
Eczema, Atopic [description not available]	2.98	4	0
Dermatitis, Atopic A chronic inflammatory genetically determined disease of the skin marked by increased ability to form reagin (IgE), with increased susceptibility to allergic rhinitis and asthma, and hereditary disposition to a lowered threshold for pruritus. It is manifested by lichenification, excoriation, and crusting, mainly on the flexural surfaces of the elbow and knee. In infants it is known as infantile eczema.	2.98	4	0
Bacterial Disease [description not available]	2.57	2	0
Bacterial Infections Infections by bacteria, general or unspecified.	2.57	2	0
Aura [description not available]	2.6	1	0
Absence Seizure [description not available]	2.6	1	0
Epilepsy A disorder characterized by recurrent episodes of paroxysmal brain dysfunction due to a sudden, disorderly, and excessive neuronal discharge. Epilepsy classification systems are generally based upon: (1) clinical features of the seizure episodes (e.g., motor seizure), (2) etiology (e.g., post-traumatic), (3) anatomic site of seizure origin (e.g., frontal lobe seizure), (4) tendency to spread to other structures in the brain, and (5) temporal patterns (e.g., nocturnal epilepsy). (From Adams et al., Principles of Neurology, 6th ed, p313)	2.6	1	0
Seizures Clinical or subclinical disturbances of cortical function due to a sudden, abnormal, excessive, and disorganized discharge of brain cells. Clinical manifestations include abnormal motor, sensory and psychic phenomena. Recurrent seizures are usually referred to as EPILEPSY or seizure disorder.	2.6	1	0
Hymenolepiasis Infection with tapeworms of the genus Hymenolepis.	2.6	1	0
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	8.85	11	0
Pyrosis [description not available]	2.6	1	0
Heartburn Substernal pain or burning sensation, usually associated with regurgitation of gastric juice into the esophagus.	2.6	1	0
Cicatrization The formation of fibrous tissue in the place of normal tissue during the process of WOUND HEALING. It includes scar tissue formation occurring in healing internal organs as well as in the skin after surface injuries.	2.6	1	0
Cicatrix The fibrous tissue that replaces normal tissue during the process of WOUND HEALING.	2.6	1	0
Diabetic Glomerulosclerosis [description not available]	3.45	6	0
Diabetic Nephropathies KIDNEY injuries associated with diabetes mellitus and affecting KIDNEY GLOMERULUS; ARTERIOLES; KIDNEY TUBULES; and the interstitium. Clinical signs include persistent PROTEINURIA, from microalbuminuria progressing to ALBUMINURIA of greater than 300 mg/24 h, leading to reduced GLOMERULAR FILTRATION RATE and END-STAGE RENAL DISEASE.	3.45	6	0
Acute Respiratory Distress Syndrome [description not available]	2.6	1	0
Respiratory Distress Syndrome A syndrome characterized by progressive life-threatening RESPIRATORY INSUFFICIENCY in the absence of known LUNG DISEASES, usually following a systemic insult such as surgery or major TRAUMA.	2.6	1	0
Cancer of Pancreas [description not available]	3.28	6	0
Pancreatic Neoplasms Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).	3.28	6	0
Experimental Neoplasms [description not available]	4.06	15	0
Lung Injury, Acute [description not available]	3.41	6	0
Acute Lung Injury A condition of lung damage that is characterized by bilateral pulmonary infiltrates (PULMONARY EDEMA) rich in NEUTROPHILS, and in the absence of clinical HEART FAILURE. This can represent a spectrum of pulmonary lesions, endothelial and epithelial, due to numerous factors (physical, chemical, or biological).	3.41	6	0
Chondromalacia Softening and degeneration of the CARTILAGE.	2.25	1	0
Cartilage Diseases Pathological processes involving the chondral tissue (CARTILAGE).	2.25	1	0
Diarrhea An increased liquidity or decreased consistency of FECES, such as running stool. Fecal consistency is related to the ratio of water-holding capacity of insoluble solids to total water, rather than the amount of water present. Diarrhea is not hyperdefecation or increased fecal weight.	5.7	7	1
Amentia [description not available]	2.21	1	0
Dementia An acquired organic mental disorder with loss of intellectual abilities of sufficient severity to interfere with social or occupational functioning. The dysfunction is multifaceted and involves memory, behavior, personality, judgment, attention, spatial relations, language, abstract thought, and other executive functions. The intellectual decline is usually progressive, and initially spares the level of consciousness.	2.21	1	0
Malignant Melanoma [description not available]	3.78	10	0
Melanoma A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)	3.78	10	0
Acne [description not available]	9.3	3	1
Acne Vulgaris A chronic disorder of the pilosebaceous apparatus associated with an increase in sebum secretion. It is characterized by open comedones (blackheads), closed comedones (whiteheads), and pustular nodules. The cause is unknown, but heredity and age are predisposing factors.	9.3	3	1
Recrudescence [description not available]	3.36	2	0
Aging, Premature Changes in the organism associated with senescence, occurring at an accelerated rate.	2.25	1	0
Cardiovascular Stroke [description not available]	4.02	13	0
Myocardial Infarction NECROSIS of the MYOCARDIUM caused by an obstruction of the blood supply to the heart (CORONARY CIRCULATION).	4.02	13	0
Hypertrophy General increase in bulk of a part or organ due to CELL ENLARGEMENT and accumulation of FLUIDS AND SECRETIONS, not due to tumor formation, nor to an increase in the number of cells (HYPERPLASIA).	7.25	1	0
Allergic Contact Dermatitis [description not available]	5.29	12	1
Alopecia Cicatrisata [description not available]	2.25	1	0
Lichen Ruber Planus [description not available]	2.25	1	0
Alopecia Absence of hair from areas where it is normally present.	2.25	1	0
Lichen Planus An inflammatory, pruritic disease of the skin and mucous membranes, which can be either generalized or localized. It is characterized by distinctive purplish, flat-topped papules having a predilection for the trunk and flexor surfaces. The lesions may be discrete or coalesce to form plaques. Histologically, there is a saw-tooth pattern of epidermal hyperplasia and vacuolar alteration of the basal layer of the epidermis along with an intense upper dermal inflammatory infiltrate composed predominantly of T-cells. Etiology is unknown.	2.25	1	0
Dermatitis, Allergic Contact A contact dermatitis due to allergic sensitization to various substances. These substances subsequently produce inflammatory reactions in the skin of those who have acquired hypersensitivity to them as a result of prior exposure.	5.29	12	1
Parodontosis [description not available]	2.97	4	0
Alveolar Bone Atrophy [description not available]	2.52	2	0
Periodontal Diseases Pathological processes involving the PERIODONTIUM including the gum (GINGIVA), the alveolar bone (ALVEOLAR PROCESS), the DENTAL CEMENTUM, and the PERIODONTAL LIGAMENT.	2.97	4	0
Metastase [description not available]	3.51	2	0
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	3.51	2	0
Debility [description not available]	2.25	1	0
Anaphylactic Reaction [description not available]	2.48	2	0
Anaphylaxis An acute hypersensitivity reaction due to exposure to a previously encountered ANTIGEN. The reaction may include rapidly progressing URTICARIA, respiratory distress, vascular collapse, systemic SHOCK, and death.	2.48	2	0
Cardiac Toxicity [description not available]	2.9	3	0
Cardiotoxicity Damage to the HEART or its function secondary to exposure to toxic substances such as drugs used in CHEMOTHERAPY; IMMUNOTHERAPY; or RADIATION.	2.9	3	0
Airflow Obstruction, Chronic [description not available]	2.69	2	0
Emphysema A pathological accumulation of air in tissues or organs.	2.69	2	0
Pulmonary Disease, Chronic Obstructive A disease of chronic diffuse irreversible airflow obstruction. Subcategories of COPD include CHRONIC BRONCHITIS and PULMONARY EMPHYSEMA.	2.69	2	0
Gastric Ulcer [description not available]	3.7	9	0
Stomach Ulcer Ulceration of the GASTRIC MUCOSA due to contact with GASTRIC JUICE. It is often associated with HELICOBACTER PYLORI infection or consumption of nonsteroidal anti-inflammatory drugs (NSAIDS).	3.7	9	0
Candida Infection [description not available]	3.4	6	0
Dermatomycoses Superficial infections of the skin or its appendages by any of various fungi.	2.69	3	0
Candidiasis Infection with a fungus of the genus CANDIDA. It is usually a superficial infection of the moist areas of the body and is generally caused by CANDIDA ALBICANS. (Dorland, 27th ed)	3.4	6	0
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	4.02	12	0
Cirrhosis, Liver [description not available]	3.38	6	0
Liver Cirrhosis Liver disease in which the normal microcirculation, the gross vascular anatomy, and the hepatic architecture have been variably destroyed and altered with fibrous septa surrounding regenerated or regenerating parenchymal nodules.	3.38	6	0
Adverse Drug Event [description not available]	2.58	2	0
Drug-Related Side Effects and Adverse Reactions Disorders that result from the intended use of PHARMACEUTICAL PREPARATIONS. Included in this heading are a broad variety of chemically-induced adverse conditions due to toxicity, DRUG INTERACTIONS, and metabolic effects of pharmaceuticals.	2.58	2	0
Salmonella Infections, Animal Infections in animals with bacteria of the genus SALMONELLA.	2.55	2	0
Disease Exacerbation [description not available]	3.46	7	0
Abscess, Amebic [description not available]	2.25	1	0
Amebiasis Infection with any of various amebae. It is an asymptomatic carrier state in most individuals, but diseases ranging from chronic, mild diarrhea to fulminant dysentery may occur.	2.25	1	0
MODS [description not available]	2.25	1	0
Acute Disease Disease having a short and relatively severe course.	3.37	7	0
Multiple Organ Failure A progressive condition usually characterized by combined failure of several organs such as the lungs, liver, kidney, along with some clotting mechanisms, usually postinjury or postoperative.	2.25	1	0
Heavy Metal Poisoning Poisoning that results from chronic or acute ingestion, injection, inhalation, or skin absorption of HEAVY METALS. Acute and chronic exposures can cause ANEMIA; KIDNEY and LIVER damage; PULMONARY EDEMA; MEMORY LOSS and behavioral changes; bone deformities in children; and MISCARRIAGE or PREMATURE LABOR in pregnant women.	2.25	1	0
Cancer of Prostate [description not available]	6.61	18	1
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	6.61	18	1
Atrophy, Muscle [description not available]	2.43	2	0
Muscular Atrophy Derangement in size and number of muscle fibers occurring with aging, reduction in blood supply, or following immobilization, prolonged weightlessness, malnutrition, and particularly in denervation.	2.43	2	0
Preterm Birth [description not available]	2.25	1	0
Premature Birth CHILDBIRTH before 37 weeks of PREGNANCY (259 days from the first day of the mother's last menstrual period, or 245 days after FERTILIZATION).	2.25	1	0
Carcinoma, Anaplastic [description not available]	3.23	6	0
Carcinoma A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.	3.23	6	0
Cardiometabolic Syndrome A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components not only include metabolic dysfunctions of METABOLIC SYNDROME but also HYPERTENSION, and ABDOMINAL OBESITY.	4.62	5	1
Metabolic Syndrome A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components of metabolic syndrome include ABDOMINAL OBESITY; atherogenic DYSLIPIDEMIA; HYPERTENSION; HYPERGLYCEMIA; INSULIN RESISTANCE; a proinflammatory state; and a prothrombotic (THROMBOSIS) state.	9.62	5	1
Carcinoma, Squamous Cell of Head and Neck [description not available]	2.25	1	0
Cancer of Mouth [description not available]	3.63	8	0
Invasiveness, Neoplasm [description not available]	4.28	17	0
Squamous Cell Carcinoma of Head and Neck The most common type of head and neck carcinoma that originates from cells on the surface of the NASAL CAVITY; MOUTH; PARANASAL SINUSES, SALIVARY GLANDS, and LARYNX. Mutations in TNFRSF10B, PTEN, and ING1 genes are associated with this cancer.	2.25	1	0
Mouth Neoplasms Tumors or cancer of the MOUTH.	3.63	8	0
Injury, Myocardial Reperfusion [description not available]	3.01	4	0
Vaginitis Inflammation of the vagina characterized by pain and a purulent discharge.	3.64	1	1
Injuries, Spinal Cord [description not available]	2.57	2	0
Spinal Cord Injuries Penetrating and non-penetrating injuries to the spinal cord resulting from traumatic external forces (e.g., WOUNDS, GUNSHOT; WHIPLASH INJURIES; etc.).	2.57	2	0
Alveolitis, Fibrosing [description not available]	3.22	5	0
Pulmonary Fibrosis A process in which normal lung tissues are progressively replaced by FIBROBLASTS and COLLAGEN causing an irreversible loss of the ability to transfer oxygen into the bloodstream via PULMONARY ALVEOLI. Patients show progressive DYSPNEA finally resulting in death.	3.22	5	0
Allodynia [description not available]	3.15	5	0
Blood Pressure, High [description not available]	4.06	14	0
Hypertension Persistently high systemic arterial BLOOD PRESSURE. Based on multiple readings (BLOOD PRESSURE DETERMINATION), hypertension is currently defined as when SYSTOLIC PRESSURE is consistently greater than 140 mm Hg or when DIASTOLIC PRESSURE is consistently 90 mm Hg or more.	9.06	14	0
Intestinal Diseases Pathological processes in any segment of the INTESTINE from DUODENUM to RECTUM.	2.25	1	0
B16 Melanoma [description not available]	3.83	11	0
Hyperlipemia [description not available]	3.16	5	0
Hyperlipidemias Conditions with excess LIPIDS in the blood.	3.16	5	0
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	4.58	24	0
Degenerative Disc Disease [description not available]	2.25	1	0
Intervertebral Disc Degeneration Degenerative changes in the INTERVERTEBRAL DISC due to aging or structural damage, especially to the vertebral end-plates.	2.25	1	0
Cardiac Remodeling, Ventricular [description not available]	2.61	2	0
Central Nervous System Disease [description not available]	3.23	1	0
Central Nervous System Diseases Diseases of any component of the brain (including the cerebral hemispheres, diencephalon, brain stem, and cerebellum) or the spinal cord.	3.23	1	0
ER-Negative PR-Negative HER2-Negative Breast Cancer [description not available]	2.9	3	0
Triple Negative Breast Neoplasms Breast neoplasms that do not express ESTROGEN RECEPTORS; PROGESTERONE RECEPTORS; and do not overexpress the NEU RECEPTOR/HER-2 PROTO-ONCOGENE PROTEIN.	2.9	3	0
Gouty Arthritis [description not available]	7.61	2	0
Arthritis, Gouty Arthritis, especially of the great toe, as a result of gout. Acute gouty arthritis often is precipitated by trauma, infection, surgery, etc. The initial attacks are usually monoarticular but later attacks are often polyarticular. Acute and chronic gouty arthritis are associated with accumulation of MONOSODIUM URATE in and around affected joints.	2.61	2	0
Hypomania [description not available]	3.64	2	0
Autosomal Dominant Juvenile Parkinson Disease [description not available]	2.79	3	0
Parkinsonian Disorders A group of disorders which feature impaired motor control characterized by bradykinesia, MUSCLE RIGIDITY; TREMOR; and postural instability. Parkinsonian diseases are generally divided into primary parkinsonism (see PARKINSON DISEASE), secondary parkinsonism (see PARKINSON DISEASE, SECONDARY) and inherited forms. These conditions are associated with dysfunction of dopaminergic or closely related motor integration neuronal pathways in the BASAL GANGLIA.	2.79	3	0
Alpha Virus Infections [description not available]	2.31	1	0
Dysembryoma [description not available]	2.31	1	0
Teratoma A true neoplasm composed of a number of different types of tissue, none of which is native to the area in which it occurs. It is composed of tissues that are derived from three germinal layers, the endoderm, mesoderm, and ectoderm. They are classified histologically as mature (benign) or immature (malignant). (From DeVita Jr et al., Cancer: Principles & Practice of Oncology, 3d ed, p1642)	2.31	1	0
Caries, Dental [description not available]	3.77	10	0
Dental Caries Localized destruction of the tooth surface initiated by decalcification of the enamel followed by enzymatic lysis of organic structures and leading to cavity formation. If left unchecked, the cavity may penetrate the enamel and dentin and reach the pulp.	3.77	10	0
Disease, Pulmonary [description not available]	2.68	3	0
Lung Diseases Pathological processes involving any part of the LUNG.	2.68	3	0
Cancer of Endometrium [description not available]	2.31	1	0
Endometrial Neoplasms Tumors or cancer of ENDOMETRIUM, the mucous lining of the UTERUS. These neoplasms can be benign or malignant. Their classification and grading are based on the various cell types and the percent of undifferentiated cells.	2.31	1	0
Drug Associated Myopathies [description not available]	2.31	1	0
Endomyometritis Inflammation of both the ENDOMETRIUM and the MYOMETRIUM, usually caused by infections after a CESAREAN SECTION.	2.63	2	0
Endometritis Inflammation of the ENDOMETRIUM, usually caused by intrauterine infections. Endometritis is the most common cause of postpartum fever.	2.63	2	0
Affective Psychosis, Bipolar [description not available]	3.23	1	0
Bipolar Disorder A major affective disorder marked by severe mood swings (manic or major depressive episodes) and a tendency to remission and recurrence.	3.23	1	0
Carcinoma, Ehrlich Tumor A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.	3.08	5	0
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	4.36	19	0
Infections, Klebsiella [description not available]	2.41	1	0
Klebsiella Infections Infections with bacteria of the genus KLEBSIELLA.	2.41	1	0
Skin Aging The process of aging due to changes in the structure and elasticity of the skin over time. It may be a part of physiological aging or it may be due to the effects of ultraviolet radiation, usually through exposure to sunlight.	10.45	7	2
Cardio-Renal Syndrome Condition where a primary dysfunction of either heart or kidney results in failure of the other organ (e.g., HEART FAILURE with worsening RENAL INSUFFICIENCY).	2.54	2	0
Chronic Illness [description not available]	2.94	4	0
Chronic Liver Failure [description not available]	2.15	1	0
Chronic Disease Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).	2.94	4	0
End Stage Liver Disease Final stage of a liver disease when the liver failure is irreversible and LIVER TRANSPLANTATION is needed.	2.15	1	0
Adenomyosis The extension of endometrial tissue (ENDOMETRIUM) into the MYOMETRIUM. It usually occurs in women in their reproductive years and may result in a diffusely enlarged uterus with ectopic and benign endometrial glands and stroma.	2.15	1	0
Angiogranuloma [description not available]	2.15	1	0
Nails, Ingrown Excessive lateral nail growth into the nail fold. Because the lateral margin of the nail acts as a foreign body, inflammation and granulation may result. It is caused by improperly fitting shoes and by improper trimming of the nail.	2.15	1	0
Infections, Salmonella [description not available]	2.15	1	0
Allergic Reaction [description not available]	3.37	7	0
Hypersensitivity Altered reactivity to an antigen, which can result in pathologic reactions upon subsequent exposure to that particular antigen.	3.37	7	0
Nerve Degeneration Loss of functional activity and trophic degeneration of nerve axons and their terminal arborizations following the destruction of their cells of origin or interruption of their continuity with these cells. The pathology is characteristic of neurodegenerative diseases. Often the process of nerve degeneration is studied in research on neuroanatomical localization and correlation of the neurophysiology of neural pathways.	2.81	3	0
Dehydration The condition that results from excessive loss of water from a living organism.	2.15	1	0
Psychoses [description not available]	3.78	2	1
Psychotic Disorders Disorders in which there is a loss of ego boundaries or a gross impairment in reality testing with delusions or prominent hallucinations. (From DSM-IV, 1994)	3.78	2	1
Infections, Helicobacter [description not available]	2.15	1	0
Helicobacter Infections Infections with organisms of the genus HELICOBACTER, particularly, in humans, HELICOBACTER PYLORI. The clinical manifestations are focused in the stomach, usually the gastric mucosa and antrum, and the upper duodenum. This infection plays a major role in the pathogenesis of type B gastritis and peptic ulcer disease.	2.15	1	0
Nasopharyngeal Carcinoma A carcinoma that originates in the EPITHELIUM of the NASOPHARYNX and includes four subtypes: keratinizing squamous cell, non-keratinizing, basaloid squamous cell, and PAPILLARY ADENOCARCINOMA. It is most prevalent in Southeast Asian populations and is associated with EPSTEIN-BARR VIRUS INFECTIONS. Somatic mutations associated with this cancer have been identified in NPCR, BAP1, UBAP1, ERBB2, ERBB3, MLL2, PIK3CA, KRAS, NRAS, and ARID1A genes.	7.15	1	0
Cancer of Nasopharynx [description not available]	2.69	3	0
Nasopharyngeal Neoplasms Tumors or cancer of the NASOPHARYNX.	2.69	3	0
Bone Loss, Osteoclastic [description not available]	3.2	5	0
Lung Adenocarcinoma [description not available]	7.17	1	0
Adenocarcinoma of Lung A carcinoma originating in the lung and the most common lung cancer type in never-smokers. Malignant cells exhibit distinct features such as glandular epithelial, or tubular morphology. Mutations in KRAS, EGFR, BRAF, and ERBB2 genes are associated with this cancer.	2.17	1	0
Weight Reduction [description not available]	5.11	5	2
Weight Gain Increase in BODY WEIGHT over existing weight.	7.85	3	0
Weight Loss Decrease in existing BODY WEIGHT.	10.11	5	2
Brain Inflammation [description not available]	3.23	5	0
Encephalitis Inflammation of the BRAIN due to infection, autoimmune processes, toxins, and other conditions. Viral infections (see ENCEPHALITIS, VIRAL) are a relatively frequent cause of this condition.	3.23	5	0
Brain Disorders [description not available]	2.89	4	0
Myoclonic Jerk [description not available]	2.42	2	0
Brain Diseases Pathologic conditions affecting the BRAIN, which is composed of the intracranial components of the CENTRAL NERVOUS SYSTEM. This includes (but is not limited to) the CEREBRAL CORTEX; intracranial white matter; BASAL GANGLIA; THALAMUS; HYPOTHALAMUS; BRAIN STEM; and CEREBELLUM.	2.89	4	0
Cardiac Failure [description not available]	2.87	3	0
Heart Failure A heterogeneous condition in which the heart is unable to pump out sufficient blood to meet the metabolic need of the body. Heart failure can be caused by structural defects, functional abnormalities (VENTRICULAR DYSFUNCTION), or a sudden overload beyond its capacity. Chronic heart failure is more common than acute heart failure which results from sudden insult to cardiac function, such as MYOCARDIAL INFARCTION.	2.87	3	0
Autoimmune Diabetes [description not available]	2.86	3	0
Diabetes Mellitus, Type 1 A subtype of DIABETES MELLITUS that is characterized by INSULIN deficiency. It is manifested by the sudden onset of severe HYPERGLYCEMIA, rapid progression to DIABETIC KETOACIDOSIS, and DEATH unless treated with insulin. The disease may occur at any age, but is most common in childhood or adolescence.	2.86	3	0
Acute Lymphoid Leukemia [description not available]	2.15	1	0
Precursor Cell Lymphoblastic Leukemia-Lymphoma A neoplasm characterized by abnormalities of the lymphoid cell precursors leading to excessive lymphoblasts in the marrow and other organs. It is the most common cancer in children and accounts for the vast majority of all childhood leukemias.	2.15	1	0
Dyslipidemia [description not available]	8.02	4	0
Dyslipidemias Abnormalities in the serum levels of LIPIDS, including overproduction or deficiency. Abnormal serum lipid profiles may include high total CHOLESTEROL, high TRIGLYCERIDES, low HIGH DENSITY LIPOPROTEIN CHOLESTEROL, and elevated LOW DENSITY LIPOPROTEIN CHOLESTEROL.	3.02	4	0
Hypertriglyceridemia A condition of elevated levels of TRIGLYCERIDES in the blood.	7.52	2	0
Infections, Respiratory [description not available]	2.17	1	0
Respiratory Tract Infections Invasion of the host RESPIRATORY SYSTEM by microorganisms, usually leading to pathological processes or diseases.	2.17	1	0
Food Poisoning, Salmonella [description not available]	2.17	1	0
Salmonella Food Poisoning Poisoning caused by ingestion of food harboring species of SALMONELLA. Conditions of raising, shipping, slaughtering, and marketing of domestic animals contribute to the spread of this bacterium in the food supply.	2.17	1	0
Adhesions, Tissue [description not available]	2.59	2	0
Complication, Postoperative [description not available]	5.42	5	1
Abscess, Abdominal [description not available]	2.17	1	0
Postoperative Complications Pathologic processes that affect patients after a surgical procedure. They may or may not be related to the disease for which the surgery was done, and they may or may not be direct results of the surgery.	5.42	5	1
Abdominal Abscess An abscess located in the abdominal cavity, i.e., the cavity between the diaphragm above and the pelvis below. (From Dorland, 27th ed)	2.17	1	0
Brain Swelling [description not available]	2.13	1	0
Brain Hemorrhage, Cerebral [description not available]	2.52	2	0
Brain Edema Increased intracellular or extracellular fluid in brain tissue. Cytotoxic brain edema (swelling due to increased intracellular fluid) is indicative of a disturbance in cell metabolism, and is commonly associated with hypoxic or ischemic injuries (see HYPOXIA, BRAIN). An increase in extracellular fluid may be caused by increased brain capillary permeability (vasogenic edema), an osmotic gradient, local blockages in interstitial fluid pathways, or by obstruction of CSF flow (e.g., obstructive HYDROCEPHALUS). (From Childs Nerv Syst 1992 Sep; 8(6):301-6)	2.13	1	0
Cerebral Hemorrhage Bleeding into one or both CEREBRAL HEMISPHERES including the BASAL GANGLIA and the CEREBRAL CORTEX. It is often associated with HYPERTENSION and CRANIOCEREBRAL TRAUMA.	7.52	2	0
Hematoma A collection of blood outside the BLOOD VESSELS. Hematoma can be localized in an organ, space, or tissue.	2.13	1	0
Bladder Cancer [description not available]	7.71	3	0
Urinary Bladder Neoplasms Tumors or cancer of the URINARY BLADDER.	2.71	3	0
Injuries Used with anatomic headings, animals, and sports for wounds and injuries. Excludes cell damage, for which pathology is used.	2.58	2	0
Wounds and Injuries Damage inflicted on the body as the direct or indirect result of an external force, with or without disruption of structural continuity.	2.58	2	0
Cancer of Gallbladder [description not available]	2.17	1	0
Gallbladder Neoplasms Tumors or cancer of the gallbladder.	2.17	1	0
Neovascularization, Optic Disc [description not available]	2.17	1	0
Retinal Neovascularization Formation of new blood vessels originating from the retinal veins and extending along the inner (vitreal) surface of the retina.	2.17	1	0
Brucella Infection [description not available]	2.55	2	0
Brucellosis Infection caused by bacteria of the genus BRUCELLA mainly involving the MONONUCLEAR PHAGOCYTE SYSTEM. This condition is characterized by fever, weakness, malaise, and weight loss.	2.55	2	0
Brain Vascular Disorders [description not available]	2.17	1	0
Cerebrovascular Disorders A spectrum of pathological conditions of impaired blood flow in the brain. They can involve vessels (ARTERIES or VEINS) in the CEREBRUM, the CEREBELLUM, and the BRAIN STEM. Major categories include INTRACRANIAL ARTERIOVENOUS MALFORMATIONS; BRAIN ISCHEMIA; CEREBRAL HEMORRHAGE; and others.	2.17	1	0
Tooth Erosion Progressive loss of the hard substance of a tooth by chemical processes that do not involve bacterial action. (Jablonski, Dictionary of Dentistry, 1992, p296)	2.17	1	0
Blastomyces brasiliensis Infection [description not available]	2.17	1	0
Acute Myelogenous Leukemia [description not available]	2.72	3	0
Leukemia, Myeloid, Acute Clonal expansion of myeloid blasts in bone marrow, blood, and other tissue. Myeloid leukemias develop from changes in cells that normally produce NEUTROPHILS; BASOPHILS; EOSINOPHILS; and MONOCYTES.	2.72	3	0
Constriction, Pathological [description not available]	2.17	1	0
Constriction, Pathologic The condition of an anatomical structure's being constricted beyond normal dimensions.	2.17	1	0
Anxiety Feelings or emotions of dread, apprehension, and impending disaster but not disabling as with ANXIETY DISORDERS.	2.84	3	0
Flatus [description not available]	3.56	1	1
Morbid Obesity [description not available]	3.56	1	1
Flatulence Production or presence of gas in the gastrointestinal tract which may be expelled through the anus.	3.56	1	1
Obesity, Morbid The condition of weighing two, three, or more times the ideal weight, so called because it is associated with many serious and life-threatening disorders. In the BODY MASS INDEX, morbid obesity is defined as having a BMI greater than 40.0 kg/m2.	3.56	1	1
Pheochromocytoma, Extra-Adrenal [description not available]	2.42	2	0
Neuroblastoma A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)	3.5	8	0
Pheochromocytoma A usually benign, well-encapsulated, lobular, vascular tumor of chromaffin tissue of the ADRENAL MEDULLA or sympathetic paraganglia. The cardinal symptom, reflecting the increased secretion of EPINEPHRINE and NOREPINEPHRINE, is HYPERTENSION, which may be persistent or intermittent. During severe attacks, there may be HEADACHE; SWEATING, palpitation, apprehension, TREMOR; PALLOR or FLUSHING of the face, NAUSEA and VOMITING, pain in the CHEST and ABDOMEN, and paresthesias of the extremities. The incidence of malignancy is as low as 5% but the pathologic distinction between benign and malignant pheochromocytomas is not clear. (Dorland, 27th ed; DeVita Jr et al., Cancer: Principles & Practice of Oncology, 3d ed, p1298)	2.42	2	0
ALS - Amyotrophic Lateral Sclerosis [description not available]	2.58	2	0
Amyotrophic Lateral Sclerosis A degenerative disorder affecting upper MOTOR NEURONS in the brain and lower motor neurons in the brain stem and SPINAL CORD. Disease onset is usually after the age of 50 and the process is usually fatal within 3 to 6 years. Clinical manifestations include progressive weakness, atrophy, FASCICULATION, hyperreflexia, DYSARTHRIA, dysphagia, and eventual paralysis of respiratory function. Pathologic features include the replacement of motor neurons with fibrous ASTROCYTES and atrophy of anterior SPINAL NERVE ROOTS and corticospinal tracts. (From Adams et al., Principles of Neurology, 6th ed, pp1089-94)	2.58	2	0
Asthma, Bronchial [description not available]	3.37	7	0
Asthma A form of bronchial disorder with three distinct components: airway hyper-responsiveness (RESPIRATORY HYPERSENSITIVITY), airway INFLAMMATION, and intermittent AIRWAY OBSTRUCTION. It is characterized by spasmodic contraction of airway smooth muscle, WHEEZING, and dyspnea (DYSPNEA, PAROXYSMAL).	3.37	7	0
Keloid A sharply elevated, irregularly shaped, progressively enlarging scar resulting from formation of excessive amounts of collagen in the dermis during connective tissue repair. It is differentiated from a hypertrophic scar (CICATRIX, HYPERTROPHIC) in that the former does not spread to surrounding tissues.	7.17	1	0
Adenocarcinoma Of Kidney [description not available]	2.5	2	0
Cancer of Kidney [description not available]	2.17	1	0
Carcinoma, Renal Cell A heterogeneous group of sporadic or hereditary carcinoma derived from cells of the KIDNEYS. There are several subtypes including the clear cells, the papillary, the chromophobe, the collecting duct, the spindle cells (sarcomatoid), or mixed cell-type carcinoma.	2.5	2	0
Kidney Neoplasms Tumors or cancers of the KIDNEY.	2.17	1	0
Proteinuria The presence of proteins in the urine, an indicator of KIDNEY DISEASES.	2.53	2	0
Leishmania Infection [description not available]	2.21	1	0
Leishmaniasis A disease caused by any of a number of species of protozoa in the genus LEISHMANIA. There are four major clinical types of this infection: cutaneous (Old and New World) (LEISHMANIASIS, CUTANEOUS), diffuse cutaneous (LEISHMANIASIS, DIFFUSE CUTANEOUS), mucocutaneous (LEISHMANIASIS, MUCOCUTANEOUS), and visceral (LEISHMANIASIS, VISCERAL).	2.21	1	0
Poultry Diseases Diseases of birds which are raised as a source of meat or eggs for human consumption and are usually found in barnyards, hatcheries, etc. The concept is differentiated from BIRD DISEASES which is for diseases of birds not considered poultry and usually found in zoos, parks, and the wild.	2.21	1	0
Cancer of Esophagus [description not available]	3.16	5	0
Esophageal Neoplasms Tumors or cancer of the ESOPHAGUS.	3.16	5	0
Carditis [description not available]	2.61	2	0
Myocarditis Inflammatory processes of the muscular walls of the heart (MYOCARDIUM) which result in injury to the cardiac muscle cells (MYOCYTES, CARDIAC). Manifestations range from subclinical to sudden death (DEATH, SUDDEN). Myocarditis in association with cardiac dysfunction is classified as inflammatory CARDIOMYOPATHY usually caused by INFECTION, autoimmune diseases, or responses to toxic substances. Myocarditis is also a common cause of DILATED CARDIOMYOPATHY and other cardiomyopathies.	2.61	2	0
Choline Deficiency A condition produced by a deficiency of CHOLINE in animals. Choline is known as a lipotropic agent because it has been shown to promote the transport of excess fat from the liver under certain conditions in laboratory animals. Combined deficiency of choline (included in the B vitamin complex) and all other methyl group donors causes liver cirrhosis in some animals. Unlike compounds normally considered as vitamins, choline does not serve as a cofactor in enzymatic reactions. (From Saunders Dictionary & Encyclopedia of Laboratory Medicine and Technology, 1984)	2.21	1	0
MS (Multiple Sclerosis) [description not available]	2.21	1	0
Multiple Sclerosis An autoimmune disorder mainly affecting young adults and characterized by destruction of myelin in the central nervous system. Pathologic findings include multiple sharply demarcated areas of demyelination throughout the white matter of the central nervous system. Clinical manifestations include visual loss, extra-ocular movement disorders, paresthesias, loss of sensation, weakness, dysarthria, spasticity, ataxia, and bladder dysfunction. The usual pattern is one of recurrent attacks followed by partial recovery (see MULTIPLE SCLEROSIS, RELAPSING-REMITTING), but acute fulminating and chronic progressive forms (see MULTIPLE SCLEROSIS, CHRONIC PROGRESSIVE) also occur. (Adams et al., Principles of Neurology, 6th ed, p903)	2.21	1	0
Clinically Isolated CNS Demyelinating Syndrome [description not available]	2.21	1	0
Demyelinating Diseases Diseases characterized by loss or dysfunction of myelin in the central or peripheral nervous system.	2.21	1	0
Vibrio cholerae Infection [description not available]	2.55	2	0
Cholera An acute diarrheal disease endemic in India and Southeast Asia whose causative agent is VIBRIO CHOLERAE. This condition can lead to severe dehydration in a matter of hours unless quickly treated.	2.55	2	0
Edema, Pulmonary [description not available]	2.42	2	0
Pulmonary Edema Excessive accumulation of extravascular fluid in the lung, an indication of a serious underlying disease or disorder. Pulmonary edema prevents efficient PULMONARY GAS EXCHANGE in the PULMONARY ALVEOLI, and can be life-threatening.	2.42	2	0
Bacterial Infections, Gram-Positive [description not available]	2.21	1	0
Gram-Positive Bacterial Infections Infections caused by bacteria that retain the crystal violet stain (positive) when treated by the gram-staining method.	2.21	1	0
Carbon Tetrachloride Poisoning Poisoning that results from ingestion, injection, inhalation, or skin absorption of CARBON TETRACHLORIDE.	3.93	13	0
Experimental Hepatoma [description not available]	2.71	3	0
Acute Promyelocytic Leukemia [description not available]	2.79	3	0
Leukemia, Promyelocytic, Acute An acute myeloid leukemia in which abnormal PROMYELOCYTES predominate. It is frequently associated with DISSEMINATED INTRAVASCULAR COAGULATION.	2.79	3	0
Menstruation, Painful [description not available]	2.21	1	0
Dysmenorrhea Painful menstruation.	2.21	1	0
Atrophy Decrease in the size of a cell, tissue, organ, or multiple organs, associated with a variety of pathological conditions such as abnormal cellular changes, ischemia, malnutrition, or hormonal changes.	2.25	1	0
Allergic Rhinitis [description not available]	7.37	2	0
Rhinitis, Allergic An inflammation of the NASAL MUCOSA triggered by ALLERGENS.	2.37	2	0
Acquired Immune Deficiency Syndrome [description not available]	2.21	1	0
Acquired Immunodeficiency Syndrome An acquired defect of cellular immunity associated with infection by the human immunodeficiency virus (HIV), a CD4-positive T-lymphocyte count under 200 cells/microliter or less than 14% of total lymphocytes, and increased susceptibility to opportunistic infections and malignant neoplasms. Clinical manifestations also include emaciation (wasting) and dementia. These elements reflect criteria for AIDS as defined by the CDC in 1993.	2.21	1	0
Bovine Diseases [description not available]	2.45	2	0
Intestinal Diseases, Parasitic Infections of the INTESTINES with PARASITES, commonly involving PARASITIC WORMS. Infections with roundworms (NEMATODE INFECTIONS) and tapeworms (CESTODE INFECTIONS) are also known as HELMINTHIASIS.	2.21	1	0
African Sleeping Sickness [description not available]	2.21	1	0
Trypanosomiasis, African A disease endemic among people and animals in Central Africa. It is caused by various species of trypanosomes, particularly T. gambiense and T. rhodesiense. Its second host is the TSETSE FLY. Involvement of the central nervous system produces African sleeping sickness. Nagana is a rapidly fatal trypanosomiasis of horses and other animals.	2.21	1	0
Female Genital Diseases [description not available]	3.17	1	0
Genital Diseases, Female Pathological processes involving the female reproductive tract (GENITALIA, FEMALE).	3.17	1	0
Dental Fluoroses [description not available]	2.21	1	0
Fluorosis, Dental A chronic endemic form of hypoplasia of the dental enamel caused by drinking water with a high fluorine content during the time of tooth formation, and characterized by defective calcification that gives a white chalky appearance to the enamel, which gradually undergoes brown discoloration. (Jablonski's Dictionary of Dentistry, 1992, p286)	2.21	1	0
Alcoholic Liver Diseases [description not available]	2.54	2	0
Liver Diseases, Alcoholic Liver diseases associated with ALCOHOLISM. It usually refers to the coexistence of two or more subentities, i.e., ALCOHOLIC FATTY LIVER; ALCOHOLIC HEPATITIS; and ALCOHOLIC CIRRHOSIS.	2.54	2	0
Anterior Circulation Transient Ischemic Attack [description not available]	2.08	1	0
Ischemic Attack, Transient Brief reversible episodes of focal, nonconvulsive ischemic dysfunction of the brain having a duration of less than 24 hours, and usually less than one hour, caused by transient thrombotic or embolic blood vessel occlusion or stenosis. Events may be classified by arterial distribution, temporal pattern, or etiology (e.g., embolic vs. thrombotic). (From Adams et al., Principles of Neurology, 6th ed, pp814-6)	2.08	1	0
Cardiomyopathies, Primary [description not available]	2.81	3	0
Cardiomyopathies A group of diseases in which the dominant feature is the involvement of the CARDIAC MUSCLE itself. Cardiomyopathies are classified according to their predominant pathophysiological features (DILATED CARDIOMYOPATHY; HYPERTROPHIC CARDIOMYOPATHY; RESTRICTIVE CARDIOMYOPATHY) or their etiological/pathological factors (CARDIOMYOPATHY, ALCOHOLIC; ENDOCARDIAL FIBROELASTOSIS).	2.81	3	0
Cicatrix, Hypertrophic An elevated scar, resembling a KELOID, but which does not spread into surrounding tissues. It is formed by enlargement and overgrowth of cicatricial tissue and regresses spontaneously.	2.8	3	0
Protein Folding Diseases [description not available]	2.08	1	0
Food Poisoning [description not available]	3.47	7	0
Break-Bone Fever [description not available]	2.08	1	0
Dengue An acute febrile disease transmitted by the bite of AEDES mosquitoes infected with DENGUE VIRUS. It is self-limiting and characterized by fever, myalgia, headache, and rash. SEVERE DENGUE is a more virulent form of dengue.	2.08	1	0
Lassitude [description not available]	2.08	1	0
Fatigue The state of weariness following a period of exertion, mental or physical, characterized by a decreased capacity for work and reduced efficiency to respond to stimuli.	2.08	1	0
Abnormalities, Autosome [description not available]	3.22	6	0
Chromosome-Defective Micronuclei [description not available]	2.08	1	0
Bone Cancer [description not available]	2.49	2	0
Bone Neoplasms Tumors or cancer located in bone tissue or specific BONES.	2.49	2	0
Chondrosarcoma A slowly growing malignant neoplasm derived from cartilage cells, occurring most frequently in pelvic bones or near the ends of long bones, in middle-aged and old people. Most chondrosarcomas arise de novo, but some may develop in a preexisting benign cartilaginous lesion or in patients with ENCHONDROMATOSIS. (Stedman, 25th ed)	7.1	1	0
Impaired Glucose Tolerance [description not available]	2.08	1	0
Glucose Intolerance A pathological state in which BLOOD GLUCOSE level is less than approximately 140 mg/100 ml of PLASMA at fasting, and above approximately 200 mg/100 ml plasma at 30-, 60-, or 90-minute during a GLUCOSE TOLERANCE TEST. This condition is seen frequently in DIABETES MELLITUS, but also occurs with other diseases and MALNUTRITION.	2.08	1	0
Fibrosarcoma A sarcoma derived from deep fibrous tissue, characterized by bundles of immature proliferating fibroblasts with variable collagen formation, which tends to invade locally and metastasize by the bloodstream. (Stedman, 25th ed)	2.96	4	0
Papilloma, Squamous Cell [description not available]	2.71	3	0
Papilloma A circumscribed benign epithelial tumor projecting from the surrounding surface; more precisely, a benign epithelial neoplasm consisting of villous or arborescent outgrowths of fibrovascular stroma covered by neoplastic cells. (Stedman, 25th ed)	2.71	3	0
Endotoxemia A condition characterized by the presence of ENDOTOXINS in the blood. On lysis, the outer cell wall of gram-negative bacteria enters the systemic circulation and initiates a pathophysiologic cascade of pro-inflammatory mediators.	2.73	3	0
Cachexia General ill health, malnutrition, and weight loss, usually associated with chronic disease.	2.08	1	0
Ache [description not available]	3.61	9	0
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	3.61	9	0
Cognition Disorders Disorders characterized by disturbances in mental processes related to learning, thinking, reasoning, and judgment.	3.19	5	0
Infections, Staphylococcal Skin [description not available]	2.1	1	0
Staphylococcal Skin Infections Infections to the skin caused by bacteria of the genus STAPHYLOCOCCUS.	2.1	1	0
Elevated Cholesterol [description not available]	2.49	2	0
Hypercholesterolemia A condition with abnormally high levels of CHOLESTEROL in the blood. It is defined as a cholesterol value exceeding the 95th percentile for the population.	2.49	2	0
Gastroduodenal Ulcer [description not available]	2.42	2	0
Peptic Ulcer Ulcer that occurs in the regions of the GASTROINTESTINAL TRACT which come into contact with GASTRIC JUICE containing PEPSIN and GASTRIC ACID. It occurs when there are defects in the MUCOSA barrier. The common forms of peptic ulcers are associated with HELICOBACTER PYLORI and the consumption of nonsteroidal anti-inflammatory drugs (NSAIDS).	2.42	2	0
Germinoblastoma [description not available]	2.92	4	0
Lymphoma A general term for various neoplastic diseases of the lymphoid tissue.	2.92	4	0
Polyarthritis [description not available]	2.1	1	0
Arthritis Acute or chronic inflammation of JOINTS.	2.1	1	0
Mastitis INFLAMMATION of the BREAST, or MAMMARY GLAND.	2.11	1	0
Anoxemia [description not available]	2.71	3	0
Hypoxia Sub-optimal OXYGEN levels in the ambient air of living organisms.	7.71	3	0
Vascular Calcification Deposition of calcium into the blood vessel structures. Excessive calcification of the vessels are associated with ATHEROSCLEROTIC PLAQUES formation particularly after MYOCARDIAL INFARCTION (see MONCKEBERG MEDIAL CALCIFIC SCLEROSIS) and chronic kidney diseases which in turn increase VASCULAR STIFFNESS.	7.1	1	0
Electrolytes Substances that dissociate into two or more ions, to some extent, in water. Solutions of electrolytes thus conduct an electric current and can be decomposed by it (ELECTROLYSIS). (Grant & Hackh's Chemical Dictionary, 5th ed)	2.11	1	0
HPV Infection [description not available]	2.11	1	0
Papillomavirus Infections Neoplasms of the skin and mucous membranes caused by papillomaviruses. They are usually benign but some have a high risk for malignant progression.	2.11	1	0
Demineralization, Tooth [description not available]	4.08	5	0
Bone Loss, Perimenopausal [description not available]	2.11	1	0
Osteoporosis, Postmenopausal Metabolic disorder associated with fractures of the femoral neck, vertebrae, and distal forearm. It occurs commonly in women within 15-20 years after menopause, and is caused by factors associated with menopause including estrogen deficiency.	2.11	1	0
Urethral Obstruction Partial or complete blockage in any part of the URETHRA that can lead to difficulty or inability to empty the URINARY BLADDER. It is characterized by an enlarged, often damaged, bladder with frequent urges to void.	2.11	1	0
Osteoarthritis of Knee [description not available]	2.11	1	0
Osteoarthritis, Knee Noninflammatory degenerative disease of the knee joint consisting of three large categories: conditions that block normal synchronous movement, conditions that produce abnormal pathways of motion, and conditions that cause stress concentration resulting in changes to articular cartilage. (Crenshaw, Campbell's Operative Orthopaedics, 8th ed, p2019)	2.11	1	0
Experimental Spinal Cord Ischemia [description not available]	2.11	1	0
Acute Edematous Pancreatitis [description not available]	2.66	3	0
Pancreatitis INFLAMMATION of the PANCREAS. Pancreatitis is classified as acute unless there are computed tomographic or endoscopic retrograde cholangiopancreatographic findings of CHRONIC PANCREATITIS (International Symposium on Acute Pancreatitis, Atlanta, 1992). The two most common forms of acute pancreatitis are ALCOHOLIC PANCREATITIS and gallstone pancreatitis.	2.66	3	0
Teratogenesis The formation of CONGENITAL ABNORMALITIES.	2.11	1	0
Acute Brain Injuries [description not available]	2.78	3	0
Brain Injuries Acute and chronic (see also BRAIN INJURIES, CHRONIC) injuries to the brain, including the cerebral hemispheres, CEREBELLUM, and BRAIN STEM. Clinical manifestations depend on the nature of injury. Diffuse trauma to the brain is frequently associated with DIFFUSE AXONAL INJURY or COMA, POST-TRAUMATIC. Localized injuries may be associated with NEUROBEHAVIORAL MANIFESTATIONS; HEMIPARESIS, or other focal neurologic deficits.	2.78	3	0
Primary Peritonitis [description not available]	2.11	1	0
Peritonitis INFLAMMATION of the PERITONEUM lining the ABDOMINAL CAVITY as the result of infectious, autoimmune, or chemical processes. Primary peritonitis is due to infection of the PERITONEAL CAVITY via hematogenous or lymphatic spread and without intra-abdominal source. Secondary peritonitis arises from the ABDOMINAL CAVITY itself through RUPTURE or ABSCESS of intra-abdominal organs.	2.11	1	0
Glaucoma An ocular disease, occurring in many forms, having as its primary characteristics an unstable or a sustained increase in the intraocular pressure which the eye cannot withstand without damage to its structure or impairment of its function. The consequences of the increased pressure may be manifested in a variety of symptoms, depending upon type and severity, such as excavation of the optic disk, hardness of the eyeball, corneal anesthesia, reduced visual acuity, seeing of colored halos around lights, disturbed dark adaptation, visual field defects, and headaches. (Dictionary of Visual Science, 4th ed)	2.82	3	0
Colitis Inflammation of the COLON section of the large intestine (INTESTINE, LARGE), usually with symptoms such as DIARRHEA (often with blood and mucus), ABDOMINAL PAIN, and FEVER.	2.77	3	0
American Trypanosomiasis [description not available]	2.42	2	0
Chagas Disease Infection with the protozoan parasite TRYPANOSOMA CRUZI, a form of TRYPANOSOMIASIS endemic in Central and South America. It is named after the Brazilian physician Carlos Chagas, who discovered the parasite. Infection by the parasite (positive serologic result only) is distinguished from the clinical manifestations that develop years later, such as destruction of PARASYMPATHETIC GANGLIA; CHAGAS CARDIOMYOPATHY; and dysfunction of the ESOPHAGUS or COLON.	2.42	2	0
Hepatitis INFLAMMATION of the LIVER.	3.57	3	0
Experimental Mammary Neoplasms [description not available]	2.68	3	0
Liver Steatosis [description not available]	3.08	5	0
Fatty Liver Lipid infiltration of the hepatic parenchymal cells resulting in a yellow-colored liver. The abnormal lipid accumulation is usually in the form of TRIGLYCERIDES, either as a single large droplet or multiple small droplets. Fatty liver is caused by an imbalance in the metabolism of FATTY ACIDS.	3.08	5	0
Dentin Hypersensitivity [description not available]	7.13	1	0
Disease Resistance The capacity of an organism to defend itself against pathological processes or the agents of those processes. This most often involves innate immunity whereby the organism responds to pathogens in a generic way. The term disease resistance is used most frequently when referring to plants.	2.13	1	0
Carcinoma, Small Cell Lung [description not available]	2.13	1	0
Small Cell Lung Carcinoma A form of highly malignant lung cancer that is composed of small ovoid cells (SMALL CELL CARCINOMA).	2.13	1	0
Cold Sore [description not available]	2.13	1	0
Dermatoses [description not available]	2.91	4	0
Herpes Labialis Herpes simplex, caused by type 1 virus, primarily spread by oral secretions and usually occurring as a concomitant of fever. It may also develop in the absence of fever or prior illness. It commonly involves the facial region, especially the lips and the nares. (Dorland, 27th ed.)	2.13	1	0
Skin Diseases Diseases involving the DERMIS or EPIDERMIS.	2.91	4	0
Cardiac Diseases [description not available]	2.39	2	0
Heart Diseases Pathological conditions involving the HEART including its structural and functional abnormalities.	2.39	2	0
Peripheral Nerve Injury [description not available]	2.15	1	0
Peripheral Nerve Injuries Injuries to the PERIPHERAL NERVES.	2.15	1	0
Alcoholic Hepatitis [description not available]	2.13	1	0
Hepatitis, Alcoholic INFLAMMATION of the LIVER due to ALCOHOL ABUSE. It is characterized by NECROSIS of HEPATOCYTES, infiltration by NEUTROPHILS, and deposit of MALLORY BODIES. Depending on its severity, the inflammatory lesion may be reversible or progress to LIVER CIRRHOSIS.	2.13	1	0
Cognitive Decline [description not available]	2.13	1	0
Cognitive Dysfunction Diminished or impaired mental and/or intellectual function.	2.13	1	0
Malignant Mesothelioma [description not available]	7.13	1	0
Mesothelioma A tumor derived from mesothelial tissue (peritoneum, pleura, pericardium). It appears as broad sheets of cells, with some regions containing spindle-shaped, sarcoma-like cells and other regions showing adenomatous patterns. Pleural mesotheliomas have been linked to exposure to asbestos. (Dorland, 27th ed)	7.13	1	0
Koch's Disease [description not available]	2.15	1	0
Tuberculosis Any of the infectious diseases of man and other animals caused by species of MYCOBACTERIUM TUBERCULOSIS.	7.15	1	0
Bacterial Skin Diseases [description not available]	2.15	1	0
Skin Diseases, Bacterial Skin diseases caused by bacteria.	2.15	1	0
Genome Instability [description not available]	2.04	1	0
Catheter-Associated Infections [description not available]	3.38	2	0
Infection, Postoperative Wound [description not available]	2.96	1	0
Infections, Prosthesis-Related [description not available]	3.36	2	0
Calcification, Pathologic [description not available]	2.38	2	0
Calcinosis Pathologic deposition of calcium salts in tissues.	2.38	2	0
Carcinoma, Lewis Lung A carcinoma discovered by Dr. Margaret R. Lewis of the Wistar Institute in 1951. This tumor originated spontaneously as a carcinoma of the lung of a C57BL mouse. The tumor does not appear to be grossly hemorrhagic and the majority of the tumor tissue is a semifirm homogeneous mass. (From Cancer Chemother Rep 2 1972 Nov;(3)1:325) It is also called 3LL and LLC and is used as a transplantable malignancy.	2.42	2	0
Adenoma, Basal Cell [description not available]	2.38	2	0
Adenoma A benign epithelial tumor with a glandular organization.	7.38	2	0
Muscle Contraction A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.	5.88	39	0
Complications, Pregnancy [description not available]	2.01	1	0
Hemorrhoids Swollen veins in the lower part of the RECTUM or ANUS. Hemorrhoids can be inside the anus (internal), under the skin around the anus (external), or protruding from inside to outside of the anus. People with hemorrhoids may or may not exhibit symptoms which include bleeding, itching, and pain.	2.01	1	0
Infections, Picornaviridae [description not available]	2.05	1	0
Heart Disease, Ischemic [description not available]	3.13	5	0
Myocardial Ischemia A disorder of cardiac function caused by insufficient blood flow to the muscle tissue of the heart. The decreased blood flow may be due to narrowing of the coronary arteries (CORONARY ARTERY DISEASE), to obstruction by a thrombus (CORONARY THROMBOSIS), or less commonly, to diffuse narrowing of arterioles and other small vessels within the heart. Severe interruption of the blood supply to the myocardial tissue may result in necrosis of cardiac muscle (MYOCARDIAL INFARCTION).	3.13	5	0
Gastric Diseases [description not available]	2.47	2	0
Adult Periodontitis [description not available]	2.05	1	0
Pyrexia [description not available]	2.05	1	0
Sore Throat [description not available]	2.05	1	0
Fever An abnormal elevation of body temperature, usually as a result of a pathologic process.	2.05	1	0
Pharyngitis Inflammation of the throat (PHARYNX).	2.05	1	0
Blood Loss, Postoperative [description not available]	6.61	4	1
Metabolic Acidosis [description not available]	2.41	2	0
Acidosis A pathologic condition of acid accumulation or depletion of base in the body. The two main types are RESPIRATORY ACIDOSIS and metabolic acidosis, due to metabolic acid build up.	2.41	2	0
T-Cell Lymphoma [description not available]	2.43	2	0
Lymphoma, T-Cell A group of heterogeneous lymphoid tumors representing malignant transformations of T-lymphocytes.	2.43	2	0
Blood Pressure, Low [description not available]	2.65	3	0
Hypotension Abnormally low BLOOD PRESSURE that can result in inadequate blood flow to the brain and other vital organs. Common symptom is DIZZINESS but greater negative impacts on the body occur when there is prolonged depravation of oxygen and nutrients.	2.65	3	0
Anterior Choroidal Artery Infarction [description not available]	2.45	2	0
Cerebral Infarction The formation of an area of NECROSIS in the CEREBRUM caused by an insufficiency of arterial or venous blood flow. Infarcts of the cerebrum are generally classified by hemisphere (i.e., left vs. right), lobe (e.g., frontal lobe infarction), arterial distribution (e.g., INFARCTION, ANTERIOR CEREBRAL ARTERY), and etiology (e.g., embolic infarction).	2.45	2	0
Lead Poisoning, Nervous System Injury to the nervous system secondary to exposure to lead compounds. Two distinct clinical patterns occur in children (LEAD POISONING, NERVOUS SYSTEM, CHILDHOOD) and adults (LEAD POISONING, NERVOUS SYSTEM, ADULT). In children, lead poisoning typically produces an encephalopathy. In adults, exposure to toxic levels of lead is associated with a peripheral neuropathy.	2.06	1	0
Health Care Associated Infection [description not available]	2.06	1	0
Cross Infection Any infection which a patient contracts in a health-care institution.	2.06	1	0
Pelvic Pain Pain in the pelvic region of genital and non-genital origin.	2.06	1	0
Cystitis Inflammation of the URINARY BLADDER, either from bacterial or non-bacterial causes. Cystitis is usually associated with painful urination (dysuria), increased frequency, urgency, and suprapubic pain.	2.06	1	0
Campylobacter Infection [description not available]	2.06	1	0
Herpes Simplex Virus Infection [description not available]	4.03	5	0
Herpes Simplex A group of acute infections caused by herpes simplex virus type 1 or type 2 that is characterized by the development of one or more small fluid-filled vesicles with a raised erythematous base on the skin or mucous membrane. It occurs as a primary infection or recurs due to a reactivation of a latent infection. (Dorland, 27th ed.)	4.03	5	0
Infections, Pseudomonas [description not available]	2.48	2	0
Shock, Cardiogenic Shock resulting from diminution of cardiac output in heart disease.	2.48	2	0
Pseudomonas Infections Infections with bacteria of the genus PSEUDOMONAS.	2.48	2	0
Hemorrhage, Uterine [description not available]	2.06	1	0
Abortion, Incomplete Premature loss of PREGNANCY in which not all the products of CONCEPTION have been expelled.	2.06	1	0
Uterine Hemorrhage Bleeding from blood vessels in the UTERUS, sometimes manifested as vaginal bleeding.	2.06	1	0
Encephalopathy, Toxic [description not available]	2.06	1	0
Chronic Kidney Diseases [description not available]	2.07	1	0
Renal Insufficiency, Chronic Conditions in which the KIDNEYS perform below the normal level for more than three months. Chronic kidney insufficiency is classified by five stages according to the decline in GLOMERULAR FILTRATION RATE and the degree of kidney damage (as measured by the level of PROTEINURIA). The most severe form is the end-stage renal disease (CHRONIC KIDNEY FAILURE). (Kidney Foundation: Kidney Disease Outcome Quality Initiative, 2002)	2.07	1	0
Granulocytic Leukemia, Chronic [description not available]	2.07	1	0
Leukemia, Myelogenous, Chronic, BCR-ABL Positive Clonal hematopoetic disorder caused by an acquired genetic defect in PLURIPOTENT STEM CELLS. It starts in MYELOID CELLS of the bone marrow, invades the blood and then other organs. The condition progresses from a stable, more indolent, chronic phase (LEUKEMIA, MYELOID, CHRONIC PHASE) lasting up to 7 years, to an advanced phase composed of an accelerated phase (LEUKEMIA, MYELOID, ACCELERATED PHASE) and BLAST CRISIS.	2.07	1	0
Absence Status [description not available]	2.07	1	0
Status Epilepticus A prolonged seizure or seizures repeated frequently enough to prevent recovery between episodes occurring over a period of 20-30 minutes. The most common subtype is generalized tonic-clonic status epilepticus, a potentially fatal condition associated with neuronal injury and respiratory and metabolic dysfunction. Nonconvulsive forms include petit mal status and complex partial status, which may manifest as behavioral disturbances. Simple partial status epilepticus consists of persistent motor, sensory, or autonomic seizures that do not impair cognition (see also EPILEPSIA PARTIALIS CONTINUA). Subclinical status epilepticus generally refers to seizures occurring in an unresponsive or comatose individual in the absence of overt signs of seizure activity. (From N Engl J Med 1998 Apr 2;338(14):970-6; Neurologia 1997 Dec;12 Suppl 6:25-30)	7.07	1	0
Dyskinesia Syndromes [description not available]	2.38	2	0
Movement Disorders Syndromes which feature DYSKINESIAS as a cardinal manifestation of the disease process. Included in this category are degenerative, hereditary, post-infectious, medication-induced, post-inflammatory, and post-traumatic conditions.	2.38	2	0
Caries, Cervical [description not available]	2.48	2	0
Hepatic Insufficiency Conditions in which the LIVER functions fall below the normal ranges. Severe hepatic insufficiency may cause LIVER FAILURE or DEATH. Treatment may include LIVER TRANSPLANTATION.	2.07	1	0
Facial Dermatoses Skin diseases involving the FACE.	2.08	1	0
Mucositis, Oral [description not available]	2.67	3	0
Microglossia [description not available]	2.42	2	0
Stomatitis INFLAMMATION of the soft tissues of the MOUTH, such as MUCOSA; PALATE; GINGIVA; and LIP.	2.67	3	0
Alcoholic Intoxication An acute brain syndrome which results from the excessive ingestion of ETHANOL or ALCOHOLIC BEVERAGES.	2.08	1	0
Amyloid Deposits [description not available]	2.07	1	0
Acinetobacter Infections Infections with bacteria of the genus ACINETOBACTER.	2.08	1	0
Alcoholic Pancreatitis [description not available]	2.07	1	0
Cell Transformation, Neoplastic Cell changes manifested by escape from control mechanisms, increased growth potential, alterations in the cell surface, karyotypic abnormalities, morphological and biochemical deviations from the norm, and other attributes conferring the ability to invade, metastasize, and kill.	2.41	2	0
Cholera Infantum [description not available]	2.08	1	0
Equine Diseases [description not available]	2.44	2	0
Methemoglobinemia The presence of methemoglobin in the blood, resulting in cyanosis. A small amount of methemoglobin is present in the blood normally, but injury or toxic agents convert a larger proportion of hemoglobin into methemoglobin, which does not function reversibly as an oxygen carrier. Methemoglobinemia may be due to a defect in the enzyme NADH methemoglobin reductase (an autosomal recessive trait) or to an abnormality in hemoglobin M (an autosomal dominant trait). (Dorland, 27th ed)	2.08	1	0
Plant Poisoning Poisoning by the ingestion of plants or its leaves, berries, roots or stalks. The manifestations in both humans and animals vary in severity from mild to life threatening. In animals, especially domestic animals, it is usually the result of ingesting moldy or fermented forage.	2.08	1	0
Dyskinesia, Medication-Induced [description not available]	2.08	1	0
Dyskinesia, Drug-Induced Abnormal movements, including HYPERKINESIS; HYPOKINESIA; TREMOR; and DYSTONIA, associated with the use of certain medications or drugs. Muscles of the face, trunk, neck, and extremities are most commonly affected. Tardive dyskinesia refers to abnormal hyperkinetic movements of the muscles of the face, tongue, and neck associated with the use of neuroleptic agents (see ANTIPSYCHOTIC AGENTS). (Adams et al., Principles of Neurology, 6th ed, p1199)	2.08	1	0
Entamoeba histolytica Infection [description not available]	2.01	1	0
Deafness, Transitory [description not available]	2.01	1	0
Hearing Loss A general term for the complete or partial loss of the ability to hear from one or both ears.	2.01	1	0
Back Injuries General or unspecified injuries to the posterior part of the trunk. It includes injuries to the muscles of the back.	2.01	1	0
Wounds, Penetrating Wounds caused by objects penetrating the skin.	2.01	1	0
Diseases of Immune System [description not available]	2.33	2	0
Immune System Diseases Disorders caused by abnormal or absent immunologic mechanisms, whether humoral, cell-mediated, or both.	2.33	2	0
Injuries, Radiation [description not available]	3.03	5	0
Experimental Radiation Injuries [description not available]	3.19	6	0
Hyperoxia An abnormal increase in the amount of oxygen in the tissues and organs.	1.94	1	0
Ascites Accumulation or retention of free fluid within the peritoneal cavity.	1.94	1	0
Christmas Disease [description not available]	1.94	1	0
Deficiency, Factor 7 [description not available]	1.94	1	0
Autosomal Hemophilia A [description not available]	1.94	1	0
Hemophilia B A deficiency of blood coagulation factor IX inherited as an X-linked disorder. (Also known as Christmas Disease, after the first patient studied in detail, not the holy day.) Historical and clinical features resemble those in classic hemophilia (HEMOPHILIA A), but patients present with fewer symptoms. Severity of bleeding is usually similar in members of a single family. Many patients are asymptomatic until the hemostatic system is stressed by surgery or trauma. Treatment is similar to that for hemophilia A. (From Cecil Textbook of Medicine, 19th ed, p1008)	1.94	1	0
Factor VII Deficiency An autosomal recessive characteristic or a coagulation disorder acquired in association with VITAMIN K DEFICIENCY. FACTOR VII is a Vitamin K dependent glycoprotein essential to the extrinsic pathway of coagulation.	1.94	1	0
Hemophilia A The classic hemophilia resulting from a deficiency of factor VIII. It is an inherited disorder of blood coagulation characterized by a permanent tendency to hemorrhage.	1.94	1	0
Tachyarrhythmia [description not available]	2.34	2	0
Tachycardia Abnormally rapid heartbeat, usually with a HEART RATE above 100 beats per minute for adults. Tachycardia accompanied by disturbance in the cardiac depolarization (cardiac arrhythmia) is called tachyarrhythmia.	2.34	2	0
Dermatitis, Eczematous [description not available]	3.04	5	0
Dermatitis, Occupational A recurrent contact dermatitis caused by substances found in the work place.	3.06	5	0
Eczema A pruritic papulovesicular dermatitis occurring as a reaction to many endogenous and exogenous agents (Dorland, 27th ed).	3.04	5	0
Autosomal Chromosome Disorders [description not available]	2.36	2	0
Acute Rheumatic Fever [description not available]	1.93	1	0
Di Guglielmo Disease [description not available]	2.39	2	0
Leukemia, Erythroblastic, Acute A myeloproliferative disorder characterized by neoplastic proliferation of erythroblastic and myeloblastic elements with atypical erythroblasts and myeloblasts in the peripheral blood.	2.39	2	0
Peripheral Nerve Diseases [description not available]	2.02	1	0
Peripheral Nervous System Diseases Diseases of the peripheral nerves external to the brain and spinal cord, which includes diseases of the nerve roots, ganglia, plexi, autonomic nerves, sensory nerves, and motor nerves.	2.02	1	0
Hives [description not available]	1.92	1	0
Urticaria A vascular reaction of the skin characterized by erythema and wheal formation due to localized increase of vascular permeability. The causative mechanism may be allergy, infection, or stress.	1.92	1	0
Cheilitis Granulomatosa [description not available]	2.01	1	0
Hay Fever [description not available]	2.02	1	0
Rhinitis, Allergic, Nonseasonal [description not available]	2.02	1	0
Rhinitis, Allergic, Seasonal Allergic rhinitis that occurs at the same time every year. It is characterized by acute CONJUNCTIVITIS with lacrimation and ITCHING, and regarded as an allergic condition triggered by specific ALLERGENS.	2.02	1	0
Rhinitis, Allergic, Perennial Inflammation of the mucous membrane of the nose similar to that found in hay fever except that symptoms persist throughout the year. The causes are usually air-borne allergens, particularly dusts, feathers, molds, animal fur, etc.	2.02	1	0
Group A Strep Infection [description not available]	2.02	1	0
Streptococcal Infections Infections with bacteria of the genus STREPTOCOCCUS.	2.02	1	0
Arteriosclerosis Thickening and loss of elasticity of the walls of ARTERIES of all sizes. There are many forms classified by the types of lesions and arteries involved, such as ATHEROSCLEROSIS with fatty lesions in the ARTERIAL INTIMA of medium and large muscular arteries.	3.99	5	0
Apolipoprotein B-100, Familial Defective [description not available]	2.02	1	0
Hyperlipoproteinemia Type II A group of familial disorders characterized by elevated circulating cholesterol contained in either LOW-DENSITY LIPOPROTEINS alone or also in VERY-LOW-DENSITY LIPOPROTEINS (pre-beta lipoproteins).	2.02	1	0
Delayed Hypersensitivity [description not available]	3.32	2	0
Kahler Disease [description not available]	2.02	1	0
Multiple Myeloma A malignancy of mature PLASMA CELLS engaging in monoclonal immunoglobulin production. It is characterized by hyperglobulinemia, excess Bence-Jones proteins (free monoclonal IMMUNOGLOBULIN LIGHT CHAINS) in the urine, skeletal destruction, bone pain, and fractures. Other features include ANEMIA; HYPERCALCEMIA; and RENAL INSUFFICIENCY.	2.02	1	0
Infections, Chlamydia [description not available]	2.02	1	0
Chlamydia Infections Infections with bacteria of the genus CHLAMYDIA.	2.02	1	0
Hormone-Dependent Neoplasms [description not available]	2.02	1	0
Dermatitis Seborrheica [description not available]	2.03	1	0
Dermatitis, Seborrheic A chronic inflammatory disease of the skin with unknown etiology. It is characterized by moderate ERYTHEMA, dry, moist, or greasy (SEBACEOUS GLAND) scaling and yellow crusted patches on various areas, especially the scalp, that exfoliate as dandruff. Seborrheic dermatitis is common in children and adolescents with HIV INFECTIONS.	2.03	1	0
Nervous System Disorders [description not available]	2.38	2	0
Nervous System Diseases Diseases of the central and peripheral nervous system. This includes disorders of the brain, spinal cord, cranial nerves, peripheral nerves, nerve roots, autonomic nervous system, neuromuscular junction, and muscle.	2.38	2	0
Cancer of Gastrointestinal Tract [description not available]	2.04	1	0
Central Nervous System Neoplasm [description not available]	2.04	1	0
Central Nervous System Neoplasms Benign and malignant neoplastic processes that arise from or secondarily involve the brain, spinal cord, or meninges.	2.04	1	0
Asymmetric Diabetic Proximal Motor Neuropathy [description not available]	2.04	1	0
Diabetic Neuropathies Peripheral, autonomic, and cranial nerve disorders that are associated with DIABETES MELLITUS. These conditions usually result from diabetic microvascular injury involving small blood vessels that supply nerves (VASA NERVORUM). Relatively common conditions which may be associated with diabetic neuropathy include third nerve palsy (see OCULOMOTOR NERVE DISEASES); MONONEUROPATHY; mononeuropathy multiplex; diabetic amyotrophy; a painful POLYNEUROPATHY; autonomic neuropathy; and thoracoabdominal neuropathy. (From Adams et al., Principles of Neurology, 6th ed, p1325)	2.04	1	0
Deficiency, Vitamin E [description not available]	1.96	1	0
Pulmonary Hypertension [description not available]	1.96	1	0
Hypertension, Pulmonary Increased VASCULAR RESISTANCE in the PULMONARY CIRCULATION, usually secondary to HEART DISEASES or LUNG DISEASES.	1.96	1	0
Bronchospasm [description not available]	2.66	3	0
Bronchial Spasm Spasmodic contraction of the smooth muscle of the bronchi.	2.66	3	0
Contact Dermatitis [description not available]	5.13	18	0
Dermatitis, Contact A type of acute or chronic skin reaction in which sensitivity is manifested by reactivity to materials or substances coming in contact with the skin. It may involve allergic or non-allergic mechanisms.	5.13	18	0
Abnormalities, Drug-Induced Congenital abnormalities caused by medicinal substances or drugs of abuse given to or taken by the mother, or to which she is inadvertently exposed during the manufacture of such substances. The concept excludes abnormalities resulting from exposure to non-medicinal chemicals in the environment.	1.96	1	0
Cheilitis Inflammation of the lips. It is of various etiologies and degrees of pathology.	2.89	4	0
Blood Loss, Surgical Loss of blood during a surgical procedure.	5.25	2	2
Cancer of Pituitary [description not available]	2.38	2	0
Pituitary Neoplasms Neoplasms which arise from or metastasize to the PITUITARY GLAND. The majority of pituitary neoplasms are adenomas, which are divided into non-secreting and secreting forms. Hormone producing forms are further classified by the type of hormone they secrete. Pituitary adenomas may also be characterized by their staining properties (see ADENOMA, BASOPHIL; ADENOMA, ACIDOPHIL; and ADENOMA, CHROMOPHOBE). Pituitary tumors may compress adjacent structures, including the HYPOTHALAMUS, several CRANIAL NERVES, and the OPTIC CHIASM. Chiasmal compression may result in bitemporal HEMIANOPSIA.	2.38	2	0
Aneuploid [description not available]	1.98	1	0
Burning Mouth Syndrome A group of painful oral symptoms associated with a burning or similar sensation. There is usually a significant organic component with a degree of functional overlay; it is not limited to the psychophysiologic group of disorders.	1.98	1	0
Erythema Redness of the skin produced by congestion of the capillaries. This condition may result from a variety of disease processes.	1.98	1	0
Behavior Disorders [description not available]	2.65	3	0
Sensation Disorders Disorders of the special senses (i.e., VISION; HEARING; TASTE; and SMELL) or somatosensory system (i.e., afferent components of the PERIPHERAL NERVOUS SYSTEM).	1.98	1	0
Mental Disorders Psychiatric illness or diseases manifested by breakdowns in the adaptational process expressed primarily as abnormalities of thought, feeling, and behavior producing either distress or impairment of function.	2.65	3	0
Muscle Relaxation That phase of a muscle twitch during which a muscle returns to a resting position.	3.24	6	0
Hyperplasia An increase in the number of cells in a tissue or organ without tumor formation. It differs from HYPERTROPHY, which is an increase in bulk without an increase in the number of cells.	2.38	2	0
Cirrhoses, Experimental Liver [description not available]	1.98	1	0
Mouth Diseases Diseases involving the MOUTH.	1.98	1	0
Lip Diseases Diseases involving the LIP.	1.98	1	0
Granulocytic Leukemia [description not available]	2.39	2	0
Leukemia, Myeloid Form of leukemia characterized by an uncontrolled proliferation of the myeloid lineage and their precursors (MYELOID PROGENITOR CELLS) in the bone marrow and other sites.	2.39	2	0
Ankylosing Spondylarthritis [description not available]	1.99	1	0
Spondylitis, Ankylosing A chronic inflammatory condition affecting the axial joints, such as the SACROILIAC JOINT and other intervertebral or costovertebral joints. It occurs predominantly in young males and is characterized by pain and stiffness of joints (ANKYLOSIS) with inflammation at tendon insertions.	1.99	1	0
Hand Dermatosis [description not available]	1.99	1	0
Hand Dermatoses Skin diseases involving the HANDS.	1.99	1	0
Bronchitis Inflammation of the large airways in the lung including any part of the BRONCHI, from the PRIMARY BRONCHI to the TERTIARY BRONCHI.	1.99	1	0
B-Cell Lymphoma [description not available]	2.4	2	0
Lymphoma, B-Cell A group of heterogeneous lymphoid tumors generally expressing one or more B-cell antigens or representing malignant transformations of B-lymphocytes.	2.4	2	0
Cytomegalic Inclusion Disease [description not available]	2.91	1	0
Cytomegalovirus Infections Infection with CYTOMEGALOVIRUS, characterized by enlarged cells bearing intranuclear inclusions. Infection may be in almost any organ, but the salivary glands are the most common site in children, as are the lungs in adults.	2.91	1	0
Infections, Coronavirus [description not available]	1.99	1	0
Rotavirus Infections Infection with any of the rotaviruses. Specific infections include human infantile diarrhea, neonatal calf diarrhea, and epidemic diarrhea of infant mice.	1.99	1	0
Coronavirus Infections Virus diseases caused by the CORONAVIRUS genus. Some specifics include transmissible enteritis of turkeys (ENTERITIS, TRANSMISSIBLE, OF TURKEYS); FELINE INFECTIOUS PERITONITIS; and transmissible gastroenteritis of swine (GASTROENTERITIS, TRANSMISSIBLE, OF SWINE).	1.99	1	0
Cancer of Larynx [description not available]	2	1	0
Laryngeal Neoplasms Cancers or tumors of the LARYNX or any of its parts: the GLOTTIS; EPIGLOTTIS; LARYNGEAL CARTILAGES; LARYNGEAL MUSCLES; and VOCAL CORDS.	2	1	0
Hepatoblastoma A malignant neoplasm occurring in young children, primarily in the liver, composed of tissue resembling embryonal or fetal hepatic epithelium, or mixed epithelial and mesenchymal tissues. (Stedman, 25th ed)	2	1	0
Carcinoma, Oat Cell [description not available]	2	1	0
Carcinoma, Small Cell An anaplastic, highly malignant, and usually bronchogenic carcinoma composed of small ovoid cells with scanty neoplasm. It is characterized by a dominant, deeply basophilic nucleus, and absent or indistinct nucleoli. (From Stedman, 25th ed; Holland et al., Cancer Medicine, 3d ed, p1286-7)	2	1	0
Acute Hypercapnic Respiratory Failure [description not available]	2	1	0
Respiratory Insufficiency Failure to adequately provide oxygen to cells of the body and to remove excess carbon dioxide from them. (Stedman, 25th ed)	2	1	0
Dermatitis, Periocular [description not available]	2	1	0
Dermatitis, Perioral A papular eruption of unknown etiology that progresses to residual papular erythema and scaling usually confined to the area of the mouth, and almost exclusively occurring in young women. It may also be localized or extend to involve the eyelids and adjacent glabella area of the forehead (periocular dermatitis). (Dorland, 28th ed)	2	1	0
Arterial Obstructive Diseases [description not available]	2	1	0
Arterial Occlusive Diseases Pathological processes which result in the partial or complete obstruction of ARTERIES. They are characterized by greatly reduced or absence of blood flow through these vessels. They are also known as arterial insufficiency.	2	1	0
Diffuse Large B-Cell Lymphoma [description not available]	2	1	0
Lymphoma, Large B-Cell, Diffuse Malignant lymphoma composed of large B lymphoid cells whose nuclear size can exceed normal macrophage nuclei, or more than twice the size of a normal lymphocyte. The pattern is predominantly diffuse. Most of these lymphomas represent the malignant counterpart of B-lymphocytes at midstage in the process of differentiation.	2	1	0
Atopic Hypersensitivity [description not available]	2.65	3	0
Hypertension, Renal Persistent high BLOOD PRESSURE due to KIDNEY DISEASES, such as those involving the renal parenchyma, the renal vasculature, or tumors that secrete RENIN.	2	1	0
Cell Transformation, Viral An inheritable change in cells manifested by changes in cell division and growth and alterations in cell surface properties. It is induced by infection with a transforming virus.	2.38	2	0
Age-Related Macular Degeneration [description not available]	2.92	1	0
Macular Degeneration Degenerative changes in the RETINA usually of older adults which results in a loss of vision in the center of the visual field (the MACULA LUTEA) because of damage to the retina. It occurs in dry and wet forms.	2.92	1	0
Arbovirus Infections Infections caused by arthropod-borne viruses, general or unspecified.	1.95	1	0
Dermatitis Exfoliativa [description not available]	1.95	1	0
Allergy, Food [description not available]	2.35	2	0
Dermatitis, Exfoliative The widespread involvement of the skin by a scaly, erythematous dermatitis occurring either as a secondary or reactive process to an underlying cutaneous disorder (e.g., atopic dermatitis, psoriasis, etc.), or as a primary or idiopathic disease. It is often associated with the loss of hair and nails, hyperkeratosis of the palms and soles, and pruritus. (From Dorland, 27th ed)	1.95	1	0
Food Hypersensitivity Gastrointestinal disturbances, skin eruptions, or shock due to allergic reactions to allergens in food.	2.35	2	0
Dermatitis Medicamentosa [description not available]	3.34	7	0
Arthritis, Juvenile Chronic [description not available]	1.95	1	0
Arthritis, Juvenile Arthritis in children, with onset before 16 years of age. The terms juvenile rheumatoid arthritis (JRA) and juvenile idiopathic arthritis (JIA) refer to classification systems for chronic arthritis in children. Only one subtype of juvenile arthritis (polyarticular-onset, rheumatoid factor-positive) clinically resembles adult rheumatoid arthritis and is considered its childhood equivalent.	1.95	1	0
Hyperventilation A pulmonary ventilation rate faster than is metabolically necessary for the exchange of gases. It is the result of an increased frequency of breathing, an increased tidal volume, or a combination of both. It causes an excess intake of oxygen and the blowing off of carbon dioxide.	1.95	1	0
Arrhythmia [description not available]	1.95	1	0
Arrhythmias, Cardiac Any disturbances of the normal rhythmic beating of the heart or MYOCARDIAL CONTRACTION. Cardiac arrhythmias can be classified by the abnormalities in HEART RATE, disorders of electrical impulse generation, or impulse conduction.	1.95	1	0
Bile Duct Obstruction [description not available]	1.95	1	0
Cholestasis Impairment of bile flow due to obstruction in small bile ducts (INTRAHEPATIC CHOLESTASIS) or obstruction in large bile ducts (EXTRAHEPATIC CHOLESTASIS).	1.95	1	0
Allergy, Drug [description not available]	3.28	2	0
Drug Hypersensitivity Immunologically mediated adverse reactions to medicinal substances used legally or illegally.	3.28	2	0
Circulatory Collapse [description not available]	2.36	2	0
Shock A pathological condition manifested by failure to perfuse or oxygenate vital organs.	2.36	2	0
Bright Disease A historical classification which is no longer used. It described acute glomerulonephritis, acute nephritic syndrome, or acute nephritis. Named for Richard Bright.	1.98	1	0
Chronic Kidney Failure [description not available]	1.98	1	0
Glomerulonephritis Inflammation of the renal glomeruli (KIDNEY GLOMERULUS) that can be classified by the type of glomerular injuries including antibody deposition, complement activation, cellular proliferation, and glomerulosclerosis. These structural and functional abnormalities usually lead to HEMATURIA; PROTEINURIA; HYPERTENSION; and RENAL INSUFFICIENCY.	1.98	1	0
Kidney Failure, Chronic The end-stage of CHRONIC RENAL INSUFFICIENCY. It is characterized by the severe irreversible kidney damage (as measured by the level of PROTEINURIA) and the reduction in GLOMERULAR FILTRATION RATE to less than 15 ml per min (Kidney Foundation: Kidney Disease Outcome Quality Initiative, 2002). These patients generally require HEMODIALYSIS or KIDNEY TRANSPLANTATION.	1.98	1	0
Bronchial Hyperreactivity Tendency of the smooth muscle of the tracheobronchial tree to contract more intensely in response to a given stimulus than it does in the response seen in normal individuals. This condition is present in virtually all symptomatic patients with asthma. The most prominent manifestation of this smooth muscle contraction is a decrease in airway caliber that can be readily measured in the pulmonary function laboratory.	6.98	1	0
Foreign-Body Reaction Chronic inflammation and granuloma formation around irritating foreign bodies.	1.98	1	0
Acid Aspiration Syndrome [description not available]	1.98	1	0
Pneumonia, Aspiration A type of lung inflammation resulting from the aspiration of food, liquid, or gastric contents into the upper RESPIRATORY TRACT.	1.98	1	0
Adenoma, beta-Cell [description not available]	2.38	2	0
Insulinoma A benign tumor of the PANCREATIC BETA CELLS. Insulinoma secretes excess INSULIN resulting in HYPOGLYCEMIA.	2.38	2	0
Anesthesia A state characterized by loss of feeling or sensation. This depression of nerve function is usually the result of pharmacologic action and is induced to allow performance of surgery or other painful procedures.	1.97	1	0
Rachitis [description not available]	1.97	1	0
Anesthesia Related Hyperthermia [description not available]	1.97	1	0
Benign Infantile Myoclonic Epilepsy [description not available]	1.97	1	0
Atherosclerotic Parkinsonism [description not available]	1.97	1	0
Epilepsies, Myoclonic A clinically diverse group of epilepsy syndromes characterized either by myoclonic seizures or by myoclonus in association with other seizure types. Myoclonic epilepsy syndromes are divided into three subtypes based on etiology: familial, cryptogenic, and symptomatic.	1.97	1	0
Parkinson Disease, Secondary Conditions which feature clinical manifestations resembling primary Parkinson disease that are caused by a known or suspected condition. Examples include parkinsonism caused by vascular injury, drugs, trauma, toxin exposure, neoplasms, infections and degenerative or hereditary conditions. Clinical features may include bradykinesia, rigidity, parkinsonian gait, and masked facies. In general, tremor is less prominent in secondary parkinsonism than in the primary form. (From Joynt, Clinical Neurology, 1998, Ch38, pp39-42)	1.97	1	0
Cytomegalovirus A genus of the family HERPESVIRIDAE, subfamily BETAHERPESVIRINAE, infecting the salivary glands, liver, spleen, lungs, eyes, and other organs, in which they produce characteristically enlarged cells with intranuclear inclusions. Infection with Cytomegalovirus is also seen as an opportunistic infection in AIDS.	1.97	1	0
Cystic Fibrosis of Pancreas [description not available]	1.96	1	0
Cystic Fibrosis An autosomal recessive genetic disease of the EXOCRINE GLANDS. It is caused by mutations in the gene encoding the CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR expressed in several organs including the LUNG, the PANCREAS, the BILIARY SYSTEM, and the SWEAT GLANDS. Cystic fibrosis is characterized by epithelial secretory dysfunction associated with ductal obstruction resulting in AIRWAY OBSTRUCTION; chronic RESPIRATORY INFECTIONS; PANCREATIC INSUFFICIENCY; maldigestion; salt depletion; and HEAT PROSTRATION.	1.96	1	0
Ventricular Fibrillation A potentially lethal cardiac arrhythmia that is characterized by uncoordinated extremely rapid firing of electrical impulses (400-600/min) in HEART VENTRICLES. Such asynchronous ventricular quivering or fibrillation prevents any effective cardiac output and results in unconsciousness (SYNCOPE). It is one of the major electrocardiographic patterns seen with CARDIAC ARREST.	1.97	1	0
Actinic Reticuloid Syndrome [description not available]	2.36	2	0
Cocarcinogenesis The combination of two or more different factors in the production of cancer.	1.97	1	0
Adipocere [description not available]	1.97	1	0
Adrenal Cancer [description not available]	1.97	1	0
Coronary Heart Disease [description not available]	2.36	2	0
Coronary Disease An imbalance between myocardial functional requirements and the capacity of the CORONARY VESSELS to supply sufficient blood flow. It is a form of MYOCARDIAL ISCHEMIA (insufficient blood supply to the heart muscle) caused by a decreased capacity of the coronary vessels.	2.36	2	0
Aggression Behavior which may be manifested by destructive and attacking action which is verbal or physical, by covert attitudes of hostility or by obstructionism.	1.96	1	0
Adenoma, Prostatic [description not available]	1.95	1	0
Prostatic Hyperplasia Increase in constituent cells in the PROSTATE, leading to enlargement of the organ (hypertrophy) and adverse impact on the lower urinary tract function. This can be caused by increased rate of cell proliferation, reduced rate of cell death, or both.	1.95	1	0
Hamartoma A focal malformation resembling a neoplasm, composed of an overgrowth of mature cells and tissues that normally occur in the affected area.	6.95	1	0
Keratoderma Blennorrhagicum [description not available]	1.95	1	0
Itching [description not available]	1.95	1	0
Acanthosis Nigricans A circumscribed melanosis consisting of a brown-pigmented, velvety verrucosity or fine papillomatosis appearing in the axillae and other body folds. It occurs in association with endocrine disorders, underlying malignancy, administration of certain drugs, or as in inherited disorder.	6.95	1	0
Keratosis Any horny growth such as a wart or callus.	1.95	1	0
Pruritus An intense itching sensation that produces the urge to rub or scratch the skin to obtain relief.	1.95	1	0
Lichen Simplex Chronicus [description not available]	2.35	2	0
Neurodermatitis An extremely variable eczematous skin disease that is presumed to be a response to prolonged vigorous scratching, rubbing, or pinching to relieve intense pruritus. It varies in intensity, severity, course, and morphologic expression in different individuals. Neurodermatitis is believed by some to be psychogenic. The circumscribed or localized form is often referred to as lichen simplex chronicus.	2.35	2	0
Anterior Optic Neuritis [description not available]	1.94	1	0
Optic Neuritis Inflammation of the optic nerve. Commonly associated conditions include autoimmune disorders such as MULTIPLE SCLEROSIS, infections, and granulomatous diseases. Clinical features include retro-orbital pain that is aggravated by eye movement, loss of color vision, and contrast sensitivity that may progress to severe visual loss, an afferent pupillary defect (Marcus-Gunn pupil), and in some instances optic disc hyperemia and swelling. Inflammation may occur in the portion of the nerve within the globe (neuropapillitis or anterior optic neuritis) or the portion behind the globe (retrobulbar neuritis or posterior optic neuritis).	1.94	1	0
Focal Neurologic Deficits [description not available]	1.94	1	0
Psychoses, Drug [description not available]	2.35	2	0
Atypical Lipoma [description not available]	2.86	1	0
Lipoma A benign tumor composed of fat cells (ADIPOCYTES). It can be surrounded by a thin layer of connective tissue (encapsulated), or diffuse without the capsule.	2.86	1	0
Symptom Cluster [description not available]	1.95	1	0
Action Tremor [description not available]	1.95	1	0
Syndrome A characteristic symptom complex.	1.95	1	0
Tremor Cyclical movement of a body part that can represent either a physiologic process or a manifestation of disease. Intention or action tremor, a common manifestation of CEREBELLAR DISEASES, is aggravated by movement. In contrast, resting tremor is maximal when there is no attempt at voluntary movement, and occurs as a relatively frequent manifestation of PARKINSON DISEASE.	1.95	1	0
Dementia Praecox [description not available]	3.33	1	1
Schizophrenia A severe emotional disorder of psychotic depth characteristically marked by a retreat from reality with delusion formation, HALLUCINATIONS, emotional disharmony, and regressive behavior.	3.33	1	1
Experimental Leukemia [description not available]	1.95	1	0
Ataxia Impairment of the ability to perform smoothly coordinated voluntary movements. This condition may affect the limbs, trunk, eyes, pharynx, larynx, and other structures. Ataxia may result from impaired sensory or motor function. Sensory ataxia may result from posterior column injury or PERIPHERAL NERVE DISEASES. Motor ataxia may be associated with CEREBELLAR DISEASES; CEREBRAL CORTEX diseases; THALAMIC DISEASES; BASAL GANGLIA DISEASES; injury to the RED NUCLEUS; and other conditions.	1.95	1	0
Distorted Hearing [description not available]	1.95	1	0
Day Blindness [description not available]	1.95	1	0
Empyema, Gall Bladder [description not available]	1.94	1	0
Cholecystitis Inflammation of the GALLBLADDER; generally caused by impairment of BILE flow, GALLSTONES in the BILIARY TRACT, infections, or other diseases.	1.94	1	0
Celiac Sprue [description not available]	1.94	1	0
Ileitis Inflammation of any segment of the ILEUM and the ILEOCECAL VALVE.	1.94	1	0
Celiac Disease A malabsorption syndrome that is precipitated by the ingestion of foods containing GLUTEN, such as wheat, rye, and barley. It is characterized by INFLAMMATION of the SMALL INTESTINE, loss of MICROVILLI structure, failed INTESTINAL ABSORPTION, and MALNUTRITION.	1.94	1	0
Bagassosis A diffuse parenchymal lung disease caused by inhaled dust from processing SUGARCANE (bagasse), usually in the manufacturing of wallboard.	1.94	1	0
Pneumoconiosis A diffuse parenchymal lung disease caused by inhalation of dust and by tissue reaction to their presence. These inorganic, organic, particulate, or vaporized matters usually are inhaled by workers in their occupational environment, leading to the various forms (ASBESTOSIS; BYSSINOSIS; and others). Similar air pollution can also have deleterious effects on the general population.	1.94	1	0

gallic acid

Description

Cross-References

Synonyms (132)

Research Excerpts

Overview

Effects

Actions

Treatment

Toxicity

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Dosage Studied

Roles (9)

Drug Classes (1)

Pathways (1)

Protein Targets (92)

Potency Measurements

Inhibition Measurements

Activation Measurements

Other Measurements

Biological Processes (513)

Molecular Functions (133)

Ceullar Components (108)

Bioassays (592)

Research

Studies (4,595)

Market Indicators

Research Demand Index: 63.61

Study Types

gallic acid

Description

Cross-References

Synonyms (132)

Research Excerpts

Overview

Effects

Actions

Treatment

Toxicity

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Dosage Studied

Roles (9)

Drug Classes (1)

Pathways (1)

Protein Targets (92)

Potency Measurements

Inhibition Measurements

Activation Measurements

Other Measurements

Biological Processes (513)

Molecular Functions (133)

Ceullar Components (108)

Bioassays (592)

Research

Studies (4,595)

Market Indicators

Research Demand Index: 63.61

Study Types

Related Drugs (2,485)

Related Conditions (826)