chlorogenic acid profile

caffeoylquinic acid: Antiviral Agent; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

chlorogenate : A monocarboxylic acid anion that is the conjugate base of chlorogenic acid; major species at pH 7.3. [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	1794427
CHEMBL ID	284616
CHEBI ID	16112
CHEBI ID	95271
SCHEMBL ID	19466
MeSH ID	M0004165

Synonym
BIDD:ER0453
MLS002153805
smr000857273
trans-chlorogenic acid
BRD-K47114202-001-06-2
5-o-(3,4-dihydroxycinnamoyl)-l-quinic acid
[1s-(1alpha,3beta,4alpha,5alpha)]3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid
CHEBI:16112 ,
202650-88-2
edit(1s,3r,4r,5r)-3-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid
SDCCGMLS-0066467.P001
nsc-70861
3-o-caffeoylquinic acid
PRESTWICK3_000427
PRESTWICK_112
cas-327-97-9
BPBIO1_000456
PRESTWICK2_000427
ACON1_000581
327-97-9
3-(3,4-dihydroxycinnamoyl)quinic acid
3-caffeoylquinic acid
cyclohexanecarboxylic acid, 3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxy-, (1s,3r,4r,5r)-
heriguard
NSC70861 ,
NSC407296 ,
SPECTRUM5_000733
BSPBIO_000414
nsc-407296
[1s-(1alpha,3beta,4alpha,5alpha)]-3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid
hlorogenic acid
1,3,4,5-tetrahydroxycyclohexanecarboxylic acid 3-(3,4-dihydroxycinnamate)
3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy] 1,4,5-trihydroxycyclohexanecarboxylic acid
3-o-(3,4-dihydroxycinnamoyl)-d-quinic acid
cyclohexanecarboxylic acid, 3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxy-, [1s-(1alpha,3beta,4alpha,5alpha)]-
cyclohexanecarboxylic acid, 3-[[(2e)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxy-, (1s,3r,4r,5r)-
nsc 70861
einecs 206-325-6
ccris 1400
cyclohexanecarboxylic acid, 3-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,4,5-trihydroxy-, (1s-(1-alpha,3-beta,4-alpha,5-alpha))-
nsc 407296
caffeoyl quinic acid
C00852
chlorogenic acid ,
chlorogenate
BSPBIO_003353
SPECTRUM210800
NCGC00168941-01
NCGC00168941-03
NCGC00168941-02
3 caffeoylquinic acid
acid, 3-caffeoylquinic
acid, chlorogenic
cyclohexanecarboxylic acid, 3-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,4,5-trihydroxy-, (1s-(1alpha,3beta,4alpha,5alpha))-
3-o-caffeoyl-d-quinic acid
chlorogenic acid, >=95% (titration)
D54CAE3D-CDDA-455D-A28E-77FC9EFE4A43
AC-6032
32CF6D13-8F08-485F-B79E-F8A6AC318E07
quinic acid, 3-caffeoyl-, e-
quinic acid, 5-caffeoyl-
trans-5-o-caffeoylquinic acid
trans-caffeic acid 5-o-d-quinate
CHEMBL284616 ,
5-cqa
cp chlorogenic acid
BMSE000387
1,3,4,5-tetrahydroxycyclohexanecarboxylic acid 3-(3,4-dihydroxycinnamate
(1s,3r,4r,5r)-3-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxycyclohexanecarboxylic acid
chlorogenic acid (8ci)
(1s,3r,4r,5r)-3-[(e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylic acid
HMS1569E16
HMS1923C11
caffeoylquinic acid
HMS2096E16
cyclohexanecarboxylic acid, 3-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,4,5-trihydroxy-, (1s,3r,4r,5r)-
(1r,3s,4s,5s)-3-[(e)-3-(3,4-dihydroxy-phenyl)-acryloyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic acid
5-caffeoyl quinic acid
3-[3-(3,4-dihydroxy-phenyl)-acryloyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic acid
(1s,3r,4r,5r)-3-[(e)-3-(3,4-dihydroxy-phenyl)-acryloyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic acid
bdbm50327036
(1s,3r,4r,5r,e)-3-(3-(3,4-dihydroxyphenyl)acryloyloxy)-1,4,5-trihydroxycyclohexanecarboxylic acid
3-[(e)-3-(3,4-dihydroxy-phenyl)-acryloyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic acid
chlorogenicacid
dtxsid3024786 ,
dtxcid604786
tox21_202495
NCGC00260044-01
AKOS015955866
HMS2235F03
CCG-38471
3-trans-caffeoylquinic acid
3-caffeoylquinate
3-(3,4-dihydroxycinnamoyl)quinate
cyclohexanecarboxylic acid, 3-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,4,5-trihydroxy-, (1s-(1-.alpha.,3-.beta.,4-.alpha.,5-.alpha.))-
cyclohexanecarboxylic acid, 3-(((2e)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-1,4,5-trihydroxy-, (1s,3r,4r,5r)-
chlorogenic acid [usp-rs]
318ADP12RI ,
chlorogenic acid [mi]
chlorogenic acid [who-dd]
(+)-chlorogenic acid
chlorogenic acid (constituent of st. john's wort) [dsc]
S2280
CWVRJTMFETXNAD-JUHZACGLSA-N
(1s,3r,4r,5r)-3-[(e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxy-cyclohexanecarboxylic acid
SCHEMBL19466
CS-3766
unii-318adp12ri
(1s,3r,4r,5r)-3-(((e)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4,5-trihydroxycyclohexane-1-carboxylic acid
HY-N0055
HMS3649E06
(1s,3r,4r,5r)-3-[(e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylicacid
mfcd00003862
(1s,3r,4r,5r)-3-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid
caffetannic acid
sr-01000841185
SR-01000841185-4
CHEBI:95271
chlorogenic acid, united states pharmacopeia (usp) reference standard
chlorogenic acid, primary pharmaceutical reference standard
hlorogenate
chlorogenic acid, european pharmacopoeia (ep) reference standard
DB12029
(e)-chlorogenic acid
Q421964
F16266
(1s,3r,4r,5r)-3-((e)-3-(3,4-dihydroxyphenyl)acryloyloxy)-1,4,5-trihydroxycyclohexanecarboxylic acid
igasuric acid
caffeylquinic acid
helianthic acid
AS-12284
SR-01000946600-1
sr-01000946600
cyclohexanecarboxylic acid,3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxy-,(1s,3r,4r,5r)-
chlorogenic-acid
(1s,3r,4r,5r)-3-(((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4,5-trihydroxycyclohexanecarboxylic acid
bdbm513080
(1s,3r,4r,5r)-3-(((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4,5-trihydroxycyclohexanecarboxylicacid
chlorogenic acid 10 microg/ml in acetonitrile
chlorogenic acid 1000 microg/ml in acetone
DTXSID101318952
gtpl12477
chlorogenic acid1510
chlorogenic acid (usp-rs)
chlorogenic acid (constituent of st. john's wort)
(1s-(1alpha,3beta,4alpha,5alpha))3-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,4,5-trihydroxycyclohexanecarboxylic acid
edit(1s,3r,4r,5r)-3-(((2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl)oxy)-1,4,5-trihydroxycyclohexane-1-carboxylic acid
chlorogenic acid (constituent of echinacea angustifolia root, echinacea pallida root, echinacea purpurea root and echinacea purpurea aerial parts)
chlorogenic acid,

Excerpt	Reference	Relevance
"Chlorogenic acid (CGA) is a phenylpropanoid compound that is well known to improve the antioxidant capacity and other biological activities. "	( Chlorogenic acid alleviates thioacetamide-induced toxicity and promotes liver development in zebrafish (Danio rerio) through the Wnt signaling pathway. Deng, Y; Fu, J; Guo, J; Liu, Y; Lu, H; Wei, L; Xiong, G; Zhang, J, 2022)	3.61
"Chlorogenic acid (CGA) is a polyphenolic substance derived from various medicinal plants."	( Chlorogenic acid delays the progression of Parkinson's disease via autophagy induction in He, CL; Long, T; Pan, R; Qin, DL; Qiu, WQ; Tang, Y; Teng, JF; Wu, AG; Wu, JM; Yu, CL; Yu, L; Zhou, XG, 2023)	3.07
"Chlorogenic acid is a polyphenolic compound that is present in various plants."	( Chlorogenic acid alleviates cerebral ischemia-induced neuroinflammation via attenuating nuclear factor kappa B activation. Kang, JB; Kim, MO; Koh, PO; Park, DJ; Shah, MA, 2022)	2.89
"Chlorogenic acid (CGA) is a natural polyphenolic compound in Lonicerae Japonicae Flos, which traditionally has the beneficial function for eyes and is commonly included in many anti-diabetic formulas."	( Chlorogenic acid improves diabetic retinopathy by alleviating blood-retinal-barrier dysfunction via inducing Nrf2 activation. Du, A; Ji, L; Lu, B; Ouyang, H; Wang, Z; Zhang, T; Zhou, L, 2022)	2.89
"Chlorogenic acid (CGA) is a natural polyphenolic compound found in human dietary products. "	( Chlorogenic Acid Inhibits Lipid Deposition by Regulating the Enterohepatic FXR-FGF15 Pathway. Gao, Z; Li, J; Wang, D; Wang, H; Wu, J; Ye, X, 2022)	3.61
"Chlorogenic acid (CGA) is a phenolic compound that is widely distributed in honeysuckle, Eucommia, fruits and vegetables. "	( The Regulatory effect of chlorogenic acid on gut-brain function and its mechanism: A systematic review. Fu, C; Liu, C; Qu, Z; Xiang, R; Zeng, L, 2022)	2.47
"Chlorogenic acid (CA) is an ingredient isolated from nature product and exerts anti-inflammatory property."	( Chlorogenic acid attenuates inflammation in LPS-induced Human gingival fibroblasts via CysLT1R/Nrf2/NLRP3 signaling. Fu, T; Guo, Y; Huang, X; Liu, Y; Qiu, S; Shen, H, 2022)	2.89
"Chlorogenic acid (CGA) is a natural polyphenolic compound."	( Chlorogenic acid alleviated liver fibrosis in methionine and choline deficient diet-induced nonalcoholic steatohepatitis in mice and its mechanism. Guo, Q; Ji, L; Kai, G; Lu, B; Miao, H; Ouyang, H; Wei, M, 2022)	2.89
"Chlorogenic acid (CGA) is a naturally occurring non-flavonoid polyphenol found in green coffee beans, teas, certain fruits, and vegetables, that exerts antiviral, antitumor, antibacterial, and antioxidant effects. "	( A review of the protective effects of chlorogenic acid against different chemicals. Hayes, AW; Karimi, G; Rashidi, R; Rezaee, R; Shakeri, A, 2022)	2.44
"Chlorogenic acid (CGA) is a functional phenolic acid widely used in food and medicine-related fields. "	( Ameliorative effects of chlorogenic acid on alcoholic liver injury in mice via gut microbiota informatics. Cheng, Y; Guo, Y; Hu, B; Jiang, W; Liu, C; Qian, H; Wang, C; Zhu, H, 2022)	2.47
"Chlorogenic acid (CGA) is a natural compound with many important pharmacological effects including anti-hypertension. "	( Moderation of gut microbiota and bile acid metabolism by chlorogenic acid improves high-fructose-induced salt-sensitive hypertension in mice. Chen, Y; Lai, S; Liang, Z; Lin, Y; Liu, Y; Tao, Y; Wang, L; Zhu, Q; Zhu, Y, 2022)	2.41
"Chlorogenic acid (CGA) is a polyphenol compound found in a variety of foods, including coffee, tea, cherries, and apples. "	( Chlorogenic Acid Inhibition of Esophageal Squamous Cell Carcinoma Metastasis Chang, HW; Chen, CH; Chen, JY; Chen, YK; Goan, YG; Hour, TC; Ngoc, NTM; Su, YF; Tung, CW, 2022)	3.61
"Chlorogenic acid (CGA) is a well-known antioxidant in coffee due to its strong ability to remove ROS."	( Chlorogenic Acid, the Main Antioxidant in Coffee, Reduces Radiation-Induced Apoptosis and DNA Damage via NF-E2-Related Factor 2 (Nrf2) Activation in Hepatocellular Carcinoma. He, X; Wu, L; Yan, D; Yan, S; Yin, X, 2022)	2.89
"Chlorogenic acid (CGA) is a natural product with anti-inflammatory effects."	( Protective effects of chlorogenic acid on inflammatory responses induced by Staphylococcus aureus and milk protein synthesis in bovine mammary epithelial cells. Bai, L; Bao, L; Chen, Y; Hao, H; Ji, Q; Lu, X; Wang, L; Wang, M; Wang, Y; Wang, Z; Zhang, M, 2022)	1.76
"Chlorogenic acid (CGA) is a highly abundant bioactive compound in green coffee beans. "	( Chlorogenic acid enhances endothelial barrier function and promotes endothelial tube formation: A proteomics approach and functional validation. Kanlaya, R; Nanthawuttiphan, S; Subkod, C; Thongboonkerd, V; Wuttimongkolchai, N, 2022)	3.61
"Chlorogenic acid (CGA) is a naturally occurring polyphenolic compound with potential anti-inflammatory and antioxidant bioactivities."	( Chlorogenic acid enhances alveolar macrophages phagocytosis in acute respiratory distress syndrome by activating G protein-coupled receptor 37 (GPR 37). Cai, N; Gao, F; He, F; Jiang, M; Wu, C, 2022)	2.89
"Chlorogenic acid is a phenolic compound found in various fruits and coffee and exerts antioxidant, anti-inflammatory, and anti-apoptotic effects."	( Chlorogenic acid alleviates the reduction of Akt and Bad phosphorylation and of phospho-Bad and 14-3-3 binding in an animal model of stroke. Kang, JB; Kim, MO; Koh, PO; Shah, MA, 2022)	2.89
"Chlorogenic acid (CGA) is a polyphenol prevalent in daily food and plants. "	( Chlorogenic acid improves food allergy through the AMPK/ACC/CPT-1 pathway. Che, H; Sun, S; Yun, Z; Zou, Z, 2022)	3.61
"Chlorogenic acid (CGA) is an ester between caffeic and quinic acid. "	( A highly active esterase from Lactobacillus helveticus hydrolyzes chlorogenic acid in sunflower meal to prevent chlorogenic acid induced greening in sunflower protein isolates. Drucker, CT; Lo Verde, C; Lyon, KA; Muniz, JC; Okumura, TLS; Owens, CP; Pepra-Ameyaw, NB; Sermet, CS; Were Senger, L, 2022)	2.4
"Chlorogenic acid (CGA) is a phenolic compound widely found in plants. "	( Preparation of polyvinyl alcohol hydrogel containing chlorogenic acid microspheres and its evaluation for use in skin wound healing. Chahardoli, F; Haddadi, R; Pourmoslemi, S; Soleimani Asl, S; Tamri, P, 2023)	2.6
"Chlorogenic acid (CGA) is a dietary polyphenol with a wide range of pharmacological effects and it has a protective effect on HIRI; however, its specific mechanism remains unclear."	( Chlorogenic Acid Alleviates Hepatic Ischemia-Reperfusion Injury by Inhibiting Oxidative Stress, Inflammation, and Mitochondria-Mediated Apoptosis In Vivo and In Vitro. Feng, Z; Geng, X; Li, K; Liu, K; Ma, X; Peng, C; Wang, L, 2023)	3.07
"Chlorogenic acid (CA) is a polyphenolic compound, found in many herbs and foods including coffee, berries and potatoes. "	( Chlorogenic acid alleviated testicular inflammation and apoptosis in tunicamycin induced endoplasmic reticulum stress. Heidari, F; Komeili-Movahhed, T; Moslehi, A, 2023)	3.8
"Chlorogenic acid is a key chemical in antioxidation and antisepsis. "	( Full-length transcriptome sequencing and transgenic tobacco revealed the key genes in the chlorogenic acid synthesis pathway of Sambucus chinensis L. Chen, M; Huang, Y; Liu, B; Quan, H; Ruan, Y; Tan, C; Wang, M; Xiao, M; Zhang, Y, )	1.8
"Chlorogenic acid (CGA) is a powerful antioxidant polyphenol molecule found in many diets and liquid beverages, playing a preventive and therapeutic role in various diseases caused by oxidative stress and inflammation. "	( Therapeutic Effects and Molecular Mechanism of Chlorogenic Acid on Polycystic Ovarian Syndrome: Role of HIF-1alpha. Shi, C; Wang, Z; Zhang, Z, 2023)	2.61
"Chlorogenic acid (CGA) is a phenolic compound appearing in coffee, honeysuckle, and eucommia that showed their potential as antioxidants and neuroprotectors."	( Neuroprotective effect of chlorogenic acid on Parkinson's disease like symptoms through boosting the autophagy in zebrafish. Finiuk, N; Gao, X; Jin, M; Liu, K; Liu, X; Rostyslav, P; Sik, A; Stoika, R; Zhang, B; Zheng, Y, 2023)	1.93
"Chlorogenic acid (CGA) is a potential botanical insecticide metabolite that naturally occurs in various plants. "	( The effect of chlorogenic acid, a potential botanical insecticide, on gene transcription and protein expression of carboxylesterases in the armyworm (Mythimna separata). Fang, Y; Gao, SJ; Lin, DJ; Wang, JD; Wang, R; Zhang, YX, 2023)	2.71
"Chlorogenic acid (CGA) is a bioactive substance with anti-inflammatory activities. "	( Chlorogenic Acid Alleviates LPS-Induced Inflammation and Oxidative Stress by Modulating CD36/AMPK/PGC-1α in RAW264.7 Macrophages. Chen, L; Gu, T; Liu, J; Lu, L; Tian, Y; Wu, W; Xu, W; Zeng, T; Zhang, Z, 2023)	3.8
"Chlorogenic acid (CGA) is a naturally occurring plant component with the purpose of alleviating hepatic lipid deposition biological activities. "	( Chlorogenic Acid Modulates Autophagy by Inhibiting the Activity of ALKBH5 Demethylase, Thereby Ameliorating Hepatic Steatosis. Cao, Q; Chen, F; Fang, X; Liu, J; Ma, D; Meng, F; Song, C; Wang, Y; Zhang, C; Zhu, Y, 2023)	3.8
"Chlorogenic acid (CGA) is an important bioactive polyphenol with extensive biological properties. "	( An optimized 3D-printed capsule scaffold utilizing artificial neural network for the targeted delivery of chlorogenic acid to the colon. Chen, H; Hu, H; Liu, Q; Liu, S; Liu, W; Wang, Y; Zhang, L; Zhao, R, 2023)	2.57
"Chlorogenic acid (CGA) is a phenolic compound contained in plant-related products that modulates many cellular functions and inhibits cell proliferation in several cancer types."	( Chlorogenic acid activates ERK1/2 and inhibits proliferation of osteosarcoma cells. Catauro, M; Chiosi, E; Illiano, M; Naviglio, S; Pacifico, S; Ragone, A; Salzillo, A; Sapio, L; Spina, A, 2020)	2.72
"Chlorogenic acid (CGA) is a small-molecule compound, that has been shown to have a wide range of biological activities, including antitumor."	( Chlorogenic acid inhibits esophageal squamous cell carcinoma growth in vitro and in vivo by downregulating the expression of BMI1 and SOX2. Feng, C; Han, Y; Huang, S; Jiang, J; Li, R; Li, X; Liu, Z; Wang, L; Zhan, Y, 2020)	2.72
"Chlorogenic acid (CGA) is a common phenolic acid found in fruits and vegetables, as well as traditional Chinese medicine, which is responsible for a variety of physiological activities."	( Chlorogenic Acid Stimulates the Thermogenesis of Brown Adipocytes by Promoting the Uptake of Glucose and the Function of Mitochondria. Guo, J; Han, X; Huang, W; You, Y; Zhan, J; Zhang, Y, 2019)	2.68
"Chlorogenic acid (CGA) is a polyphenol widely distributed in plants and plant-derived food with antioxidant and protective activities against cell stress. "	( Effects of chlorogenic acid on thermal stress tolerance in C. elegans via HIF-1, HSF-1 and autophagy. Asis, R; Carranza, ADV; Carrari, F; Chiabrando, GA; Saragusti, A, 2020)	2.39
"Chlorogenic acid is a widely distributed natural compound with many important pharmacological effects, which are found in a variety of plants. "	( Pharmacological action and potential targets of chlorogenic acid. Miao, M; Xiang, L, 2020)	2.26
"Chlorogenic acid (CA) is a phenolic compound commonly found in human plant-based diets. "	( Use of Chlorogenic Acid against Diabetes Mellitus and Its Complications. Guo, K; Yan, Y; Yang, H; Zhou, F; Zhou, X, 2020)	2.46
"Chlorogenic acid (CGA) is a phenolic compound with well-known antibacterial properties against pathogens. "	( Structural and Biochemical Analyses Reveal that Chlorogenic Acid Inhibits the Shikimate Pathway. Dev, A; Gaur, S; Katiki, M; Kumar, P; Neetu, N; Tomar, S, 2020)	2.26
"Chlorogenic acid is a type of phenolic acid found in many plants. "	( Chlorogenic acid ameliorates obesity by preventing energy balance shift in high-fat diet induced obese mice. He, X; Huang, K; Miao, T; Sheng, Y; Xu, J; Xu, W; Zhao, C; Zheng, S, 2021)	3.51
"Chlorogenic acid (CGA) is a strong phenolic antioxidant with antibacterial properties composed by a caffeoyl ester of quinic acid. "	( Interaction of chlorogenic acid with model lipid membranes and its influence on antiradical activity. Cejas, JP; Disalvo, EA; Frias, MA; Nazareno, MA; Rosa, AS, 2021)	2.42
"Chlorogenic acid (CGA) is a polyphenol compound with various pharmacological traits, such as anticancer properties."	( Chlorogenic acid induces 4T1 breast cancer tumor's apoptosis via p53, Bax, Bcl-2, and caspase-3 signaling pathways in BALB/c mice. Changizi, Z; Eidi, A; Moslehi, A; Rohani, AH, 2021)	2.79
"Chlorogenic acid is an herbal compound with various effects such as antiviral, antioxidant, and anticancer effect with low toxicity, which inhibits cell proliferation. "	( Chlorogenic acid inhibits growth of 4T1 breast cancer cells through involvement in Bax/Bcl2 pathway. Changizi, Z; Eidi, A; Moslehi, A; Rohani, AH, )	3.02
"Chlorogenic acid (CGA) is a kind of traditional Chinese medicine, abundant in honeysuckle and eucommia, and has a wide range of biological activities, and pharmacological effects. "	( Chlorogenic Acid Improves PTSD-like Symptoms and Associated Mechanisms. Chen, XD; Feng, S; Huang, H; Lu, FN; Lu, XM; Tang, JJ; Wang, YT, 2021)	3.51
"Chlorogenic acid (CGA) is a potential inhibitor of Coronavirus Disease 2019 (COVID-19). "	( Chlorogenic acid, a natural product as potential inhibitor of COVID-19: virtual screening experiment based on network pharmacology and molecular docking. Luo, SY; Tang, C; Wang, WX; Zhang, Y; Zhang, YR; Zhang, YS, 2022)	3.61
"Chlorogenic acid (CGA) is a type of polyphenolic substance that is widely extracted from many traditional Chinese medicines (eg, "	( Chlorogenic Acid Inhibits Human Glioma U373 Cell Progression via Regulating the SRC/MAPKs Signal Pathway: Based on Network Pharmacology Analysis. Chen, J; Wang, H; Zhang, F; Zhang, S; Zhou, J, 2021)	3.51
"Chlorogenic acid is a plant polyphenol with antioxidant and antimicrobial activities. "	( Chlorogenic acid induces ROS-dependent apoptosis in Fusarium fujikuroi and decreases the postharvest rot of cherry tomato. Bi, W; Kai, K; Ma, Z; Shi, W; Wang, R; Ye, Y; Zhang, D, 2021)	3.51
"Chlorogenic acid (CGA) is a phenolic compound that has been well studied for its antiviral, anti-inflammatory and immune stimulating properties. "	( Chlorogenic acid is a positive regulator of MDA5, TLR7 and NF-κB signaling pathways mediated antiviral responses against Gammacoronavirus infection. Abaidullah, M; Jia, R; Li, L; Peng, S; Song, X; Yin, Z; Zou, Y, 2021)	3.51
"Chlorogenic acid (CA) is a common phytochemical, which can attenuate neuroinflammation."	( Beneficial effects of chlorogenic acid treatment on neuroinflammation after deep hypothermic circulatory arrest may be mediated through CYLD/NF-κB signaling. Cao, H; Chen, Q; Lei, YQ; Liu, JF; Wang, ZC, 2021)	1.66
"Chlorogenic acid (CGA), which is a natural compound found in various plants, has been reported to exert notable anti‑inflammatory activities. "	( Chlorogenic acid prevents inflammatory responses in IL‑1β‑stimulated human SW‑1353 chondrocytes, a model for osteoarthritis. Dai, BL; Liu, CC; Ma, YJ; Wang, Y; Yang, H; Zhang, Q; Zhang, Y, 2017)	3.34
"Chlorogenic acid (CGA) is a quinic acid conjugate of caffeic acid, and a phytochemical found in many fruits and beverages that acts as an antioxidant. "	( Chlorogenic acid supplementation during in vitro maturation improves maturation, fertilization and developmental competence of porcine oocytes. Do, L; Nguyen, TV; Otoi, T; Sato, Y; Takagi, M; Taniguchi, M; Tanihara, F; Van Nguyen, T, 2017)	3.34
"Chlorogenic acid (CGA) is a phenolic secondary metabolite which accumulates in diverse plant tissues and can be found in several agro-industrial by-products and waste."	( Chlorogenic acid is a fungicide active against phytopathogenic fungi. de la Canal, L; Del Rio, M; Jacobi, S; Martínez, G; Pinedo, M; Regente, M, 2017)	2.62
"The chlorogenic acid (CGA) is a natural product isolated from Cecropia obtusifolia, which possesses several pharmacological properties, such as: anti-carcinogenic, neuroprotective, antioxidant, anti-inflammatory, hypoglycemic, and hypolipidemic. "	( Potential of the chlorogenic acid as multitarget agent: Insulin-secretagogue and PPAR α/γ dual agonist. Alarcon-Aguilar, FJ; de Los Angeles Fortis Barrera, M; Miranda-Perez, E; Perez-Ramos, J; Sanchez, MB; Verjan, JCG, 2017)	1.35
"Chlorogenic acid (CA) is a phenolic compound purified from coffee, fruits and their associated beverages, which possess various biological properties, such as antioxidant and anticarcinogenic activities. "	( Chlorogenic acid suppresses lipopolysaccharide‑induced nitric oxide and interleukin‑1β expression by inhibiting JAK2/STAT3 activation in RAW264.7 cells. Joo, YE; Kim, SH; Myung, DS; Park, SY; Park, YL; Rew, JS, 2017)	3.34
"Chlorogenic Acid (CGA, 3-CQA) is a most abundant isomer among caffeoylquinic acid isomers (3-, 4-, and 5-CQA), that currently known as 5-CQA as per guidelines of IUPAC."	( Chlorogenic acid (CGA): A pharmacological review and call for further research. Abbas, M; Ahmad, F; Babazadeh, D; FangFang, X; Hejazi, V; Kamboh, AA; Khan, GJ; Modarresi-Ghazani, F; Naveed, M; Shumzaid, M; WenHua, L; XiaoHui, Z, 2018)	2.64
"Chlorogenic acid (CGA) is a polyphenol found in coffee and medicinal herbs such as Lonicera japonica. "	( Effects of chlorogenic acid on carbachol-induced contraction of mouse urinary bladder. Kaneda, T; Sasaki, N; Shimizu, K; Urakawa, N, 2018)	2.31
"Chlorogenic acid (CGA) is a natural phenolic acid, which is an important component of biologically active dietary phenols isolated from various species. "	( Dietary chlorogenic acid improves growth performance of weaned pigs through maintaining antioxidant capacity and intestinal digestion and absorption function. Chen, D; Chen, J; He, J; Li, Y; Luo, J; Mao, X; Yu, B; Zheng, P, 2018)	2.36
"Chlorogenic acid (CGA) is a phenolic compound with various health-promoting properties, including antioxidant effects and a wide range of antibacterial activities. "	( Depletion of reactive oxygen species induced by chlorogenic acid triggers apoptosis-like death in Escherichia coli. Lee, B; Lee, DG, 2018)	2.18
"Chlorogenic acid (CGA) is a polyphenol present in many human dietary foods. "	( Chlorogenic Acid Improves the Regorafenib Effects in Human Hepatocellular Carcinoma Cells. Carella, N; Cavallini, A; D'Alessandro, R; Lippolis, C; Messa, C; Refolo, MG, 2018)	3.37
"Chlorogenic acid (CGA) is a natural polyphenol present in human diet and plants, possessing potent antioxidant and anti-inflammatory activities."	( Chlorogenic acid improves intestinal barrier functions by suppressing mucosa inflammation and improving antioxidant capacity in weaned pigs. Chen, D; Chen, J; He, J; Huang, Z; Luo, J; Mao, X; Yu, B; Yu, J; Zheng, P, 2018)	2.64
"Chlorogenic acids (CGAs) are a group of phenolic compounds found in worldwide consumed beverages such as coffee and green tea. "	( Chlorogenic acids inhibit glutamate dehydrogenase and decrease intracellular ATP levels in cultures of chick embryo retina cells. Calaza, KDC; Cossenza, M; Domith, I; Duarte-Silva, AT; Garcia, CG; Paes-de-Carvalho, R, 2018)	3.37
"Chlorogenic acid (CGA) is a very common dietary polyphenolic compound. "	( Silica/Polyethylene Glycol Hybrid Materials Prepared by a Sol-Gel Method and Containing Chlorogenic Acid. Capasso, L; Catauro, M; Illiano, M; Naviglio, S; Salzillo, A; Sapio, L; Tranquillo, E, 2018)	2.15
"Chlorogenic acid (CA) is a natural compound used as an antioxidant in the preparation of food, drugs, and cosmetics. "	( Water-in-oil-in-water double emulsions loaded with chlorogenic acid: release mechanisms and oxidative stability. Dima, C; Dima, S, 2018)	2.18
"Chlorogenic acid (CA) is a polyphenol compound that possesses anticancer effects on several types of tumors. "	( Chlorogenic acid inhibits osteosarcoma carcinogenesis via suppressing the STAT3/Snail pathway. Bao, Z; Han, X; Jiang, X; Yin, G; Zhang, F, 2019)	3.4
"Chlorogenic acid (5CQA) is a dietary polyphenol known for its high biological activity. "	( Antioxidative activity of chlorogenic acid relative to trolox in aqueous solution - DFT study. Marković, S; Tošović, J, 2019)	2.26
"Chlorogenic acid (CGA) is a major component of green coffee beans. "	( Bioactivity of Fermented Green Coffee Bean Extract Containing High Chlorogenic Acid and Surfactin. Jeong, Y; Kim, B; Kim, HS; Kim, I; Kim, JK; Kim, SW; Lee, BH; Lee, DS; Lee, HI; Lee, SG; Park, T, 2019)	2.19
"Chlorogenic acid (CGA) is a phenolic compound and exerts antiarthritic activities in arthritis."	( Chlorogenic Acid Inhibits BAFF Expression in Collagen-Induced Arthritis and Human Synoviocyte MH7A Cells by Modulating the Activation of the NF- Fu, X; He, F; Huang, G; Liu, H; Lyu, X; Xu, Z; Zhong, D, 2019)	2.68
"Chlorogenic acid (CGA) is a widely applied traditional Chinese medicine ingredient which can be used for the treatment of osteoporosis. "	( Chlorogenic Acid Alleviates Thiram-Induced Tibial Dyschondroplasia by Modulating Caspases, BECN1 Expression and ECM Degradation. Huang, S; Jiang, X; Li, J; Mehmood, K; Tong, X; Zhang, H; Zhang, J; Zhang, L, 2019)	3.4
"Chlorogenic acid (CGA) is a quinic acid conjugate of caffeic acid. "	( Therapeutic Promises of Chlorogenic Acid with Special Emphasis on its Anti-Obesity Property. Iqbal, MS; Kumar, R; Sharma, A; Srivastava, JK, 2020)	2.31
"Chlorogenic acid (CGA), which is a key component of coffee, has many biological effects such as anti-inflammation activity. "	( Chlorogenic acid attenuates ventricular remodeling after myocardial infarction in mice. Isobe, M; Kanno, Y; Ogawa, M; Suzuki, J; Watanabe, R; Zempo, H, 2013)	3.28
"Chlorogenic acid is a polyphenol compound abundant in coffee."	( Biogenic silver nanoparticles with chlorogenic acid as a bioreducing agent. Cho, S; Jun, SH; Kang, YH; Kim, HS; Noh, HJ; Park, Y, 2013)	1.39
"Chlorogenic acids (CGA) are a class of polyphenols noted for their health benefits. "	( The effect of processing on chlorogenic acid content of commercially available coffee. Gibson, GR; Mills, CE; Mottram, DS; Oruna-Concha, MJ; Spencer, JP, 2013)	2.13
"Chlorogenic acid is a potent phenolic antioxidant. "	( Chlorogenic acid inhibits human platelet activation and thrombus formation. Alarcón, M; Caballero, J; Fuentes, E; Palomo, I; Rojas, A, 2014)	3.29
"Chlorogenic acid is a major phenolic compound that forms a substantial part of plant foods and is an ester of caffeic acid and quinic acid. "	( Caffeic and chlorogenic acids inhibit key enzymes linked to type 2 diabetes (in vitro): a comparative study. Adefegha, SA; Ademiluyi, AO; Agunloye, OM; Akinyemi, AJ; Oboh, G, 2015)	2.24
"Chlorogenic acid is a superoxide radical scavenger with weak xanthine oxidase inhibitory activity."	( In vitro and in vivo studies on adlay-derived seed extracts: phenolic profiles, antioxidant activities, serum uric acid suppression, and xanthine oxidase inhibitory effects. Dong, Y; Lin, L; Su, G; Sun-Waterhouse, D; Wang, X; Zhao, M; Zhu, D, 2014)	1.12
"Chlorogenic acid (CGA) is a well-known natural antioxidant in human diet. "	( Pharmacologic overview of systemic chlorogenic acid therapy on experimental wound healing. Bagdas, D; Cinkilic, N; Etoz, BC; Gul, NY; Gul, Z; Gurun, MS; Inan, S; Ozyigit, MO; Tas, S; Topal, A; Turacozen, O; Ziyanok, S, 2014)	2.12
"Chlorogenic acid (CHA) is an antioxidant polyphenol prevalent in human diet, with coffee, fruits, and vegetables being its main source. "	( Anti-inflammatory effect of chlorogenic acid on the IL-8 production in Caco-2 cells and the dextran sulphate sodium-induced colitis symptoms in C57BL/6 mice. Bae, MJ; Ogiwara, H; Satsu, H; Shimizu, M; Shin, HS; Totsuka, M; Zhao, Z, 2015)	2.15
"Chlorogenic acid is a water-soluble agent that promotes CFTR-mediated Cl(-) transport in mouse and human sinonasal epithelium. "	( Chlorogenic Acid Activates CFTR-Mediated Cl- Secretion in Mice and Humans: Therapeutic Implications for Chronic Rhinosinusitis. Cho, DY; Dunlap, QA; Illing, EA; Skinner, DF; Sorscher, EJ; Woodworth, BA; Zhang, S, 2015)	3.3
"Neochlorogenic acid (NCA) is a natural polyphenolic compound found in dried fruits and other plants."	( Neochlorogenic Acid Inhibits Lipopolysaccharide-Induced Activation and Pro-inflammatory Responses in BV2 Microglial Cells. Choi, SY; Hur, J; Kim, M; Lee, P, 2015)	1.55
"Chlorogenic acid (CGA) is a phenolic acid that ubiquitously exists in fruits. "	( Chlorogenic acid increased 5-hydroxymethylfurfural formation when heating fructose alone or with aspartic acid at two pH levels. Bai, W; Huang, C; Lin, X; Ou, S; Pei, K; Wu, T; Zhang, G; Zhang, Z; Zou, Y, 2016)	3.32
"Chlorogenic acid (CGA) is an important compound in E."	( Antidepressant Potential of Chlorogenic Acid-Enriched Extract from Eucommia ulmoides Oliver Bark with Neuron Protection and Promotion of Serotonin Release through Enhancing Synapsin I Expression. Cao, S; Chen, H; Li, H; Qin, D; Tang, Y; Wu, J; Yang, L, 2016)	1.45
"Chlorogenic acid (CGA) is a polyphenol derivative that widely exists in higher plants like fruits, vegetables, black teas, and some traditional Chinese medicines. "	( Application of a nanostructured platform and imprinted sol-gel film for determination of chlorogenic acid in food samples. Gonzaga, FB; Goulart, MOF; Kubota, LT; Lima, PR; Miguel, EM; Ribeiro, CM; Santos, WJR; Silva, CBD; Silva, JDS, 2016)	2.1
"Chlorogenic acid is a well known natural product with important bioactivities. "	( Synthesis, Anti-HCV, Antioxidant and Reduction of Intracellular Reactive Oxygen Species Generation of a Chlorogenic Acid Analogue with an Amide Bond Replacing the Ester Bond. Daneshtalab, M; Hattori, M; Ma, CM; Wang, LN; Wang, W, 2016)	2.09
"Chlorogenic acid (CRA) is an abundant phenolic compound in the human diet. "	( Role of potassium channels in chlorogenic acid-induced apoptotic volume decrease and cell cycle arrest in Candida albicans. Lee, DG; Yun, J, 2017)	2.19
"Chlorogenic acid is a quinyl ester of caffeic acid that has increased hydrophilicity and also shows stronger XO inhibitory activity compared with caffeic acid."	( Hydrophilic ester-bearing chlorogenic acid binds to a novel domain to inhibit xanthine oxidase. Chen, CS; Huang, SH; Huang, ST; Lai, ZY; Lin, CM; Wang, SH; Yu, SH, 2009)	1.37
"Chlorogenic acid (CGA) is a naturally occurring phenolic acid in human diet. "	( Chlorogenic acid inhibits lipopolysaccharide-induced cyclooxygenase-2 expression in RAW264.7 cells through suppressing NF-kappaB and JNK/AP-1 activation. Fu, J; Huang, H; Kong, X; Luo, L; Shan, J; Yin, Z; Zhao, Z, 2009)	3.24
"Chlorogenic acid is a phenolic compound present in coffee, apples, pears, berries, almonds, artichokes, and aubergines."	( Chlorogenic acid attenuates adhesion molecules upregulation in IL-1beta-treated endothelial cells. Chang, T; Chang, WC; Chen, CH; Lee, MF; Yu, YM, 2010)	2.52
"Chlorogenic acid is an ester of caffeic acid, quinic acid, and a phenolic compound that has antibacterial, antifungal, antioxidant, and antitumor activities."	( Studies on a chlorogenic acid-producing endophytic fungi isolated from Eucommia ulmoides Oliver. Bai, L; Chen, X; Li, S; Sang, X; Zhang, S, 2010)	1.45
"Chlorogenic acid is a natural potent antioxidant. "	( Chlorogenic acid UVA–UVB photostability. Almeida, RL; Barros, SB; Filho, CA; Rivelli, DP; Ropke, CD; Sawada, TC, )	3.02
"Chlorogenic acid is a major polyphenolic component of many plants and beverages, and is particularly abundant in coffee. "	( Neuroprotective effects of chlorogenic acid on scopolamine-induced amnesia via anti-acetylcholinesterase and anti-oxidative activities in mice. Hong, SI; Jang, CG; Jo, TH; Kim, HC; Kim, JA; Kim, YB; Kwon, SH; Lee, CK; Lee, HK; Lee, SY; Park, YI, 2010)	2.1
"Chlorogenic acid (CA) is a well-known ester of caffeic acid present in some food. "	( Comparison of the binding affinity of chlorogenic acid with two serum albumins. Du, W; Wang, Y; Xu, J; Zhang, T, 2011)	2.08
"Chlorogenic acids (CGAs) are a family of esters formed between quinic acid and certain cinnamic acids, most commonly caffeic, p-coumaric and ferulic acid. "	( Profiling the chlorogenic acids of Rudbeckia hirta, Helianthus tuberosus, Carlina acaulis and Symphyotrichum novae-angliae leaves by LC-MS(n). Deshpande, S; Jaiswal, R; Kuhnert, N, )	1.93
"Chlorogenic acid (CGA) is a phenolic compound formed by the esterification of caffeic and quinic acids."	( Chlorogenic acid inhibits the formation of advanced glycation end products and associated protein cross-linking. Jeong, IH; Kim, CS; Kim, J; Kim, JM; Kim, JS; Lee, YM, 2011)	2.53
"Chlorogenic acid is an ester of caffeic and quinic acids, and is one of the most widely consumed polyphenols because it is abundant in foods, especially coffee. "	( Coffee polyphenol caffeic acid but not chlorogenic acid increases 5'AMP-activated protein kinase and insulin-independent glucose transport in rat skeletal muscle. Egawa, T; Hayashi, T; Kurogi, E; Ma, X; Oshima, R; Tsuda, S, 2012)	2.09
"Chlorogenic acids (CGAs) are a group of soluble phenolic compounds that are produced by a variety of plants, including Coffea canephora (robusta coffee). "	( Purification, crystallization and preliminary X-ray diffraction analysis of a hydroxycinnamoyl-CoA shikimate/quinate hydroxycinnamoyltransferase (HCT) from Coffea canephora involved in chlorogenic acid biosynthesis. Lallemand, LA; McCarthy, AA; McCarthy, JG; McSweeney, S, 2012)	2.01
"Chlorogenic acid (CGA) is a plant polyphenol with known antioxidant properties. "	( The coffee constituent chlorogenic acid induces cellular DNA damage and formation of topoisomerase I- and II-DNA complexes in cells. Austin, C; Burgos-Morón, E; Calderón-Montaño, JM; López-Lázaro, M; Mateos, S; Orta, ML; Pastor, N; Pérez-Guerrero, C, 2012)	2.13
"Chlorogenic acids (CGAs) are a group of phenolic secondary metabolites produced by certain plant species and an important component of coffee (Coffea spp.). "	( A structural basis for the biosynthesis of the major chlorogenic acids found in coffee. Acajjaoui, S; Jez, JM; Lallemand, LA; Lee, SG; McCarthy, AA; McCarthy, JG; McSweeney, S; Timmins, J; Wang, Y; Zubieta, C, 2012)	2.07
"Chlorogenic acid is a well-known antioxidant and has more isomers according to the difference in binding location and number of caffeic on quinic acid. "	( Antioxidant and DNA-protective activities of chlorogenic acid isomers. Hu, QP; Liu, Y; Xu, JG, 2012)	2.08
"Chlorogenic acid (CGA) is a type of polyphenol with anti-inflammatory, antioxidant activities. "	( Chlorogenic acid reduces liver inflammation and fibrosis through inhibition of toll-like receptor 4 signaling pathway. Dang, X; Dong, L; Jia, M; Jiang, J; Lu, X; Shi, H; Zhao, G; Zhao, J, 2013)	3.28
"Chlorogenic acid (CGA) is a natural organic phenolic compound that is found in many plants, fruits and vegetables. "	( Antihyperalgesic activity of chlorogenic acid in experimental neuropathic pain. Bagdas, D; Cinkilic, N; Gurun, MS; Ozboluk, HY; Ozyigit, MO, 2013)	2.12
"Chlorogenic acid is a suitable component for the quality control of C. "	( [Determination of chlorogenic acid in chrysanthemum morifolium Ramat.flower]. Chen, Z; Li, Z; Liao, L; Lin, S, 1999)	2.08
"Chlorogenic acid is a major polyphenol in coffee; coffee drinkers consume up to 1 g chlorogenic acid/d."	( Consumption of high doses of chlorogenic acid, present in coffee, or of black tea increases plasma total homocysteine concentrations in humans. Hollman, PC; Katan, MB; Olthof, MR; Zock, PL, 2001)	1.32
"Chlorogenic acid, which is an ester of caffeic acid with quinic acid, also stimulated the formation of the hydroxyl radicals."	( Enhancement by catechols of hydroxyl-radical formation in the presence of ferric ions and hydrogen peroxide. Ishii, T; Iwahashi, H; Kido, R; Morishita, H; Sugata, R, 1989)	1
"Chlorogenic acid is a naturally occurring phenolic compound found in all higher plants. "	( Thermal stability of 5-o-caffeoylquinic acid in aqueous solutions at different heating conditions. Dawidowicz, AL; Typek, R, 2010)	1.8

Excerpt	Reference	Relevance
"Chlorogenic acid has an antioxidant capacity and may prevent capillary regression."	( Protective effects of chlorogenic acid on capillary regression caused by disuse muscle atrophy. Fujino, H; Hirabayashi, T; Kondo, H; Lin, H; Ma, X; Maeshige, N; Nakanishi, R; Nakayama, E; Pan, H; Xing, J, 2021)	1.66
"Chlorogenic acid has an anti-obesity effect with an unclear mechanism."	( Chlorogenic acid ameliorates obesity by preventing energy balance shift in high-fat diet induced obese mice. He, X; Huang, K; Miao, T; Sheng, Y; Xu, J; Xu, W; Zhao, C; Zheng, S, 2021)	2.79
"Chlorogenic acid has a molecular structure similar to bioflavonoids that activate transepithelial Cl(-) transport in sinonasal epithelia."	( Chlorogenic Acid Activates CFTR-Mediated Cl- Secretion in Mice and Humans: Therapeutic Implications for Chronic Rhinosinusitis. Cho, DY; Dunlap, QA; Illing, EA; Skinner, DF; Sorscher, EJ; Woodworth, BA; Zhang, S, 2015)	2.58
"Chlorogenic acid (CA) has been discovered to regulate macrophage polarization in pneumonia. "	( Mechanism of chlorogenic acid in alveolar macrophage polarization in Klebsiella pneumoniae-induced pneumonia. Chen, L; He, W; Li, QR; Shen, FX; Tan, SR; Wang, HF; Wang, Z; Yang, L, 2022)	2.53
"Chlorogenic acid (1) has been shown to delay intestinal glucose absorption by inhibiting the activity of α-glucosidase (α-Glu) and α-amylase (α-Amy)."	( Synthesis and in vitro evaluation of chlorogenic acid amides as potential hypoglycemic agents and their synergistic effect with acarbose. Cardullo, N; Floresta, G; Muccilli, V; Rescifina, A; Tringali, C, 2021)	1.62
"Chlorogenic acid has an antioxidant capacity and may prevent capillary regression."	( Protective effects of chlorogenic acid on capillary regression caused by disuse muscle atrophy. Fujino, H; Hirabayashi, T; Kondo, H; Lin, H; Ma, X; Maeshige, N; Nakanishi, R; Nakayama, E; Pan, H; Xing, J, 2021)	1.66
"Chlorogenic acid has multiple biological activities such as antivirus and anti-inflammation, while few researches have revealed its therapeutic functions in neuroinflammation."	( Chlorogenic Acid Alleviates the Inflammatory Stress of LPS-Induced BV2 Cell via Interacting with TLR4-Mediated Downstream Pathway. Chai, J; Jing, P; Luo, T; Xiong, L; Xu, W, 2022)	2.89
"Chlorogenic acid (CGA) has exhibited lipid-lowering effects."	( Chlorogenic acid improves anti-lipogenic activity of metformin by positive regulating of AMPK signaling in HepG2 cells. Khorzoughi, RB; Meshkani, R; Moradi-Sardareh, H; Namvarjah, F; Panahi, G; Pasalar, P; Shokri-Afra, H, 2022)	2.89
"Chlorogenic acid (CGA) has been reported to have various biological activities, such as anti-inflammatory, anti-oxidant and anti-apoptosis effects. "	( Neuroprotective Effects of Chlorogenic Acid in a Mouse Model of Intracerebral Hemorrhage Associated with Reduced Extracellular Matrix Metalloproteinase Inducer. Li, Z; Liu, Y; Mu, Y; Wang, F; Xue, M; Yong, VW, 2022)	2.46
"Chlorogenic acid (CGA) has good antioxidant effects, but its explicit mechanism in cerebral ischaemia-reperfusion injury is still uncertain."	( Chlorogenic acid promotes angiogenesis and attenuates apoptosis following cerebral ischaemia-reperfusion injury by regulating the PI3K-Akt signalling. Fan, Y; Li, Y; Lin, K; Lin, Q; Luo, S; Yang, Y; Zhang, F; Zhou, X, 2022)	3.61
"Chlorogenic acid (CGA) has been shown to possess potent antioxidant, anti-inflammatory, and immunoprotective properties."	( Targeting TLR4/3 using chlorogenic acid ameliorates LPS+POLY I:C-induced acute respiratory distress syndrome via alleviating oxidative stress-mediated NLRP3/NF-κB axis. Jain, S; Jannu, AK; Naidu, VGM; Panda, SR; Rajdev, B; Saha, P; Sharma, P; Syamprasad, NP, 2023)	1.94
"Chlorogenic acid (CGA) has been reported to have anti-inflammatory effects and can improve memory function."	( Chlorogenic acid may improve memory function and decrease inflamation of frontal lobe in diabetic rat. Arfian, N; Kencana, SMS; Munawaroh, F; Saputri, LAAWS; Sari, DCR, 2023)	3.07
"Chlorogenic acid (CGA) has been considered as one of important active components in a number of medicinal herbs. "	( Structural Optimization of Caffeoyl Salicylate Scaffold as NO Production Inhibitors. Li, DD; Wang, Z; Xia, CJ; Xiao, W; Yu, P; Zhao, LG, 2019)	1.96
"Chlorogenic Acid (CA) has diverse, recognized health effects."	( Effects and Mechanism of Chlorogenic Acid on Weight Loss. Ban, G; Dai, J; Ding, Y; Ge, M; Li, L; Yang, H; Zhang, L; Zhong, Y, 2020)	2.3
"Chlorogenic acid has an anti-obesity effect with an unclear mechanism."	( Chlorogenic acid ameliorates obesity by preventing energy balance shift in high-fat diet induced obese mice. He, X; Huang, K; Miao, T; Sheng, Y; Xu, J; Xu, W; Zhao, C; Zheng, S, 2021)	2.79
"Chlorogenic acid (CGA) has antibacterial, antiviral, antioxidative and immunoregulatory effects, but its role in anaphylactic disease remains unclear."	( Chlorogenic Acid Alleviates Allergic Inflammatory Responses Through Regulating Th1/Th2 Balance in Ovalbumin-Induced Allergic Rhinitis Mice. Dong, F; Tan, J; Zheng, Y, 2020)	2.72
"Isochlorogenic acid (ICGA), which has medicinal value, has been discovered in various plants."	( Isochlorogenic acid (ICGA): natural medicine with potentials in pharmaceutical developments. Cao, Y; DU, HZ; Hou, XY; Jiang, H; Liu, DH; Liu, Q; Shen, Z; Wang, HN, 2020)	1.69
"Chlorogenic acid has antioxidant, anti-inflammatory, and anti-apoptotic properties."	( Chlorogenic acid alleviates neurobehavioral disorders and brain damage in focal ischemia animal models. Kang, JB; Kim, MO; Koh, PO; Park, DJ; Shah, MA, 2021)	2.79
"Chlorogenic acid (CGA) has many biological properties, including antibacterial, antioxidant and anti-inflammatory properties, and is one of the most abundant phenolic acids available in the human diet. "	( Dietary chlorogenic acid regulates gut microbiota, serum-free amino acids and colonic serotonin levels in growing pigs. Huang, F; Li, Q; Li, Y; Liu, W; Ruan, Z; Shu, X; Wu, X; Wu, Y; Yan, Y; Zhou, Q, 2018)	2.36
"Chlorogenic acid has been described as a novel polyphenol with metabolic effects on glucose homeostasis. "	( Effect of Chlorogenic Acid Administration on Glycemic Control, Insulin Secretion, and Insulin Sensitivity in Patients with Impaired Glucose Tolerance. Aceves-de la Mora, MCA; González-Ortiz, M; Martínez-Abundis, E; Ramos-Núñez, JL; Zuñiga, LY, 2018)	2.33
"Chlorogenic acid (CGA) has been reported to exhibit potent anti-inflammatory activity. "	( Design, synthesis, and anti-inflammatory activity of caffeoyl salicylate analogs as NO production inhibitors. Ding, G; Li, DD; Ni, JJ; Wang, ZZ; Xia, CJ; Xiao, W; Yu, P; Zhao, LG, 2018)	1.92
"Chlorogenic acid (CGA) has been demonstrated to possess potent neuroprotective activities against oxidative stress in various cellular models and pathological conditions."	( Chlorogenic Acid Prevents AMPA-Mediated Excitotoxicity in Optic Nerve Oligodendrocytes Through a PKC and Caspase-Dependent Pathways. Amri, M; Rebai, O, 2018)	2.64
"Chlorogenic acid has important antibacterial, antioxidant, and anti-inflammatory functions; however, the effect of CGA on BMEC and neutrophils exposed to S."	( The protective effect of chlorogenic acid on bovine mammary epithelial cells and neutrophil function. Gong, XX; Su, XS; Zhan, K; Zhao, GQ, 2018)	1.51
"Chlorogenic acid intake has been associated with decreased risk of cardiovascular disease and type 2 diabetes."	( Chlorogenic acid attenuates high-carbohydrate, high-fat diet-induced cardiovascular, liver, and metabolic changes in rats. Bhandarkar, NS; Brown, L; Panchal, SK, 2019)	2.68
"Chlorogenic acid (CGA) has prominently medicinal and nutritional values."	( In vivo protective effects of chlorogenic acid against triptolide-induced hepatotoxicity and its mechanism. Chen, RX; Cheng, YX; Cui, Y; Ding, NN; Liu, C; Wang, JM; Zhang, LL, 2018)	1.49
"Chlorogenic acid (CGA) has been shown to stimulate glucose uptake in skeletal muscle through the activation of AMPK. "	( Anti-diabetic and anti-lipidemic effects of chlorogenic acid are mediated by ampk activation. Hsu, A; Ong, KW; Tan, BK, 2013)	2.09
"Chlorogenic acid (CA) has been reported to inhibit several pathogens, but the influence of subinhibitory concentrations of CA on virulence expression of pathogens has not been fully elucidated. "	( Effect of subinhibitory concentrations of chlorogenic acid on reducing the virulence factor production by Staphylococcus aureus. Guo, Y; Li, G; Qiao, M; Wang, X; Xia, X; Xu, Y, 2014)	2.11
"Chlorogenic acid has a molecular structure similar to bioflavonoids that activate transepithelial Cl(-) transport in sinonasal epithelia."	( Chlorogenic Acid Activates CFTR-Mediated Cl- Secretion in Mice and Humans: Therapeutic Implications for Chronic Rhinosinusitis. Cho, DY; Dunlap, QA; Illing, EA; Skinner, DF; Sorscher, EJ; Woodworth, BA; Zhang, S, 2015)	2.58
"Chlorogenic acid (CGA) has been reported to prevent acetaminophen (AP)-induced hepatotoxicity when mice were pre-administered orally with CGA for consecutive 7days before AP intoxication in our previous study. "	( The therapeutic detoxification of chlorogenic acid against acetaminophen-induced liver injury by ameliorating hepatic inflammation. Ji, L; Lu, B; Sheng, Y; Zheng, Z, 2015)	2.14
"Chlorogenic acid lactones have been identified as key contributors to coffee bitterness. "	( Selective enzymatic hydrolysis of chlorogenic acid lactones in a model system and in a coffee extract. Application to reduction of coffee bitterness. Bel-Rhlid, R; Blank, I; Gartenmann, K; Kraehenbuehl, K; Mauroux, O; Page-Zoerkler, N, 2017)	2.18
"Chlorogenic acid (CGA) has potential antioxidant effects and its pharmacological action in osteoblasts is not clearly understood."	( Cytoprotective effect of chlorogenic acid against hydrogen peroxide-induced oxidative stress in MC3T3-E1 cells through PI3K/Akt-mediated Nrf2/HO-1 signaling pathway. Chen, W; Gao, J; Gu, X; Han, B; Han, D; Liu, G; Shahid, M; Shan, R; Zou, J, 2017)	1.48
"Chlorogenic acid has shown antimicrobial activity against a wide range of organisms,including bacteria, yeasts, molds, viruses, and amoebas."	( Chlorogenic Acid: Recent Advances on Its Dual Role as a Food Additive and a Nutraceutical against Metabolic Syndrome. Cisneros-Zevallos, L; Jacobo-Velázquez, DA; Santana-Gálvez, J, 2017)	2.62
"Chlorogenic acid has the best synergistic effect of 44.8%."	( Quantification of antioxidant capacity in a microemulsion system: synergistic effects of chlorogenic acid with alpha-tocopherol. Han, MY; Huang, D; Sim, WL, 2009)	1.3
"Chlorogenic acid (CHA) has been proved to be an activator of calcineurin (CN) in our previous research. "	( Interaction of calcineurin with its activator, chlorogenic acid revealed by spectroscopic methods. Jiang, M; Wei, Q; Wu, H; Xie, M; Yin, Y; Zheng, J, 2009)	2.05
"Chlorogenic acid (Chl) has been reported to possess a wide range of biological and pharmacological properties including induction of apoptosis of Bcr-Abl(+) chronic myeloid leukemia (CML) cell lines and clinical leukemia samples via inhibition of Bcr-Abl phosphorylation. "	( Involvement of ROS in chlorogenic acid-induced apoptosis of Bcr-Abl+ CML cells. Bagchi, J; Bandyopadhyay, S; Biswas, N; Chaudhuri, J; Chaudhuri, U; Chowdhury, AA; Jaisankar, P; Konar, A; Mandal, L; Manna, A; Mukherjee, T; Pal, BC; Rakshit, S, 2010)	2.12
"Chlorogenic acid (CGA) has been shown to delay intestinal glucose absorption and inhibit gluconeogenesis. "	( Chlorogenic acid stimulates glucose transport in skeletal muscle via AMPK activation: a contributor to the beneficial effects of coffee on diabetes. Hsu, A; Ong, KW; Tan, BK, 2012)	3.26
"Chlorogenic acid (CGA) has been reported to have various beneficial effects on the cardiovascular and central nervous systems. "	( Chlorogenic acid ameliorates brain damage and edema by inhibiting matrix metalloproteinase-2 and 9 in a rat model of focal cerebral ischemia. Bae, J; Bu, Y; Chang, MS; Choi, HY; Jang, HJ; Jeong, CH; Kim, KS; Kim, SM; Lee, B; Lee, JS; Lee, K; Park, JW; Park, SH, 2012)	3.26
"Neochlorogenic acid (9), which has not previously been reported from goldenseal, and chlorogenic acid (6) reached their highest levels in leaves (0.9% 9 and 0.5% 6)."	( A new glucosyl feruloyl quinic acid as a potential marker for roots and rhizomes of goldenseal, Hydrastis canadensis. Douglas, JA; Follett, JM; McNamara, CE; Parmenter, GA; Perry, NB, 2004)	0.84
"Chlorogenic acid (CGA) has been proved to be an activator of calcineurin (CN) in our previous research. "	( Calmodulin-dependent activation of calcineurin by chlorogenic acid. Jia, Z; Song, Y; Tong, L; Wei, Q; Zhang, W, 2007)	2.04

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"Chlorogenic acid (CGA) displays cognition-improving properties, but the underlying mechanisms remain unclear. "	( Chlorogenic Acid Ameliorates High-Fat and High-Fructose Diet-Induced Cognitive Impairment via Mediating the Microbiota-Gut-Brain Axis. Hu, CY; Meng, YH; Tian, D; Zhang, SQ, 2022)	3.61
"Chlorogenic acid can inhibit microglial polarization toward the M1 phenotype and improve neuroinflammation-induced cognitive dysfunction in mice by modulating these key targets in the TNF signaling pathway."	( Effect and mechanism of chlorogenic acid on cognitive dysfunction in mice by lipopolysaccharide-induced neuroinflammation. Kang, Y; Li, X; Ma, K; Si, J; Su, X; Wang, L; Xiong, S, 2023)	2.66
"Chlorogenic acid (CGA) plays a pivotal role in the regulation of the mammalian cell heat stress response."	( Chlorogenic acid ameliorates the heat stress-induced impairment of porcine Sertoli cells by suppressing oxidative stress and apoptosis. Liang, S; Qi, JJ; Sun, BX; Sun, H; Wang, DL; Yang, YW; Zhang, SX, 2024)	3.61
"Chlorogenic acid (CGA) plays a crucial role in defense response, immune regulation, and the response to abiotic stress in plants. "	( Genetic Architecture Underlying the Metabolites of Chlorogenic Acid Biosynthesis in Du, Q; Fang, Y; Li, L; Li, P; Lu, W; Quan, M; Song, F; Xiao, L; Yao, L; Zhang, D, 2021)	2.32
"Chlorogenic acid could inhibit the pulmonary fibrosis through endoplasmic reticulum stress inhibition in vivo and in vitro."	( Amelioration of bleomycin-induced pulmonary fibrosis by chlorogenic acid through endoplasmic reticulum stress inhibition. Chen, JY; Chen, Q; Dong, J; Nie, J; Shuai, W; Wang, H; Wang, YC; Xia, JM; Zhu, JX, 2017)	1.42
"Chlorogenic acid (CGA) plays an important role in protecting plants against pathogens and promoting human health. "	( Cloning and functional characterization of a p-coumaroyl quinate/shikimate 3'-hydroxylase from potato (Solanum tuberosum). Knollenberg, BJ; Lin, H; Liu, J; Tian, L; Yu, S, 2018)	1.92
"Chlorogenic acid could inhibit ER stress induced cell death and levels of indicators of ER stress caused by palmitic acid."	( Chlorogenic acid against palmitic acid in endoplasmic reticulum stress-mediated apoptosis resulting in protective effect of primary rat hepatocytes. Lv, J; Miao, L; Wu, G; Zhang, H; Zhang, Y; Zhang, Z, 2018)	2.64
"Chlorogenic acid displays several important roles in the therapeutic properties of many herbs, such as antioxidant activity, antibacterial, antiviral, scavenging free radicals and exciting central nervous system. "	( [Recent progress of potential effects and mechanisms of chlorogenic acid and its intestinal metabolites on central nervous system diseases]. Jia, W; Li, Y; Shi, XW; Xing, LN; Zhou, MM, 2015)	2.11
"Chlorogenic acid can lower blood pressure acutely, an effect that, if sustained, would benefit cardiovascular health."	( Acute effects of chlorogenic acid on nitric oxide status, endothelial function, and blood pressure in healthy volunteers: a randomized trial. Bondonno, CP; Considine, MJ; Croft, KD; Hodgson, JM; Liu, AH; Mas, E; Mubarak, A; Rich, L, 2012)	1.44

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"Chlorogenic acid treatment attenuated these increases caused by MCAO."	( Chlorogenic acid alleviates cerebral ischemia-induced neuroinflammation via attenuating nuclear factor kappa B activation. Kang, JB; Kim, MO; Koh, PO; Park, DJ; Shah, MA, 2022)	2.89
"Chlorogenic acid treatment of injured zebrafish embryos showed low-developmental toxicity."	( Chlorogenic acid-enriched extract of Ilex kudingcha C.J. Tseng tea inhibits neutrophil recruitment in injured zebrafish by promoting reverse migration via the focal adhesion pathway. Liu, X; Piao, L; Zhang, W, 2020)	2.72
"Chlorogenic acid treatment attenuated the increase in the number of TUNEL-positive cells in the cerebral cortex of MCAO animals."	( Chlorogenic acid alleviates neurobehavioral disorders and brain damage in focal ischemia animal models. Kang, JB; Kim, MO; Koh, PO; Park, DJ; Shah, MA, 2021)	2.79
"Chlorogenic acid pretreatment in OP-treated groups restored all the mentioned parameters to approach the normal values."	( The Role of Chlorogenic Acid Supplementation in Anemia and Mineral Disturbances Induced by 4-Tert-Octylphenol Toxicity. Arbid, MSS; Gomaa, NE; Koriem, KMM, 2018)	1.58
"When treated with chlorogenic acid (CGA), significant structural changes and improved functionalities of QPH were detected."	( Possible role of polypeptide-chlorogenic acid interaction in the physicochemical and sensory characteristics of quinoa-modified coffee beverage. Ji, X; Jiang, J; Wang, L; Zhao, J, 2023)	1.52
"Treatment with chlorogenic acid significantly reduced the apoptotic damage and reversed molecular alterations in cerebral cortex neurons after IR."	( Involvement of miR-27a/smurf1/ TNF-α and mitochondrial apoptotic pathway in apoptosis induced by cerebral ischemia-reperfusion injury in rats: The protective effect of chlorogenic acid. Naderi, R; Salimi, R; Shirpoor, A, 2023)	1.44
"Upon treatment with chlorogenic acid, suppression of the onset of diabetes, reduced serum glucose and insulin concentrations, improved glucose tolerance and increased body weight and visceral fat weight were observed."	( Chlorogenic acid inhibits forming of diabetes mellitus in rats induced by high-fat high-sucrose and streptozotocin. Hu, Y; Jin, C; Kang, J; Mei, Z; Peng, S; Wang, Y; Wang, Z; Xiang, M, 2020)	2.32
"Treatment with chlorogenic acid (25-50 μM) significantly decreased gene expression and concentration of proinflammatory cytokines IL-6 and IL-8 compared to LPS-treated cells."	( Chlorogenic Acid Combined with Lactobacillus plantarum 2142 Reduced LPS-Induced Intestinal Inflammation and Oxidative Stress in IPEC-J2 Cells. Farkas, O; Gálfi, P; Palócz, O; Pászti-Gere, E, 2016)	2.22

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" After preincubation of cardiomyocytes with the test compounds (100, 200 microm; 1 h) the cardiomyocytes were treated with the toxic agent, DOX (100 microm; 8 h)."	( Chemoprotective effect of plant phenolics against anthracycline-induced toxicity on rat cardiomyocytes. Part II. caffeic, chlorogenic and rosmarinic acids. Chlopcíková, S; Lichnovský, V; Miketová, P; Psotová, J; Simánek, V; Sousek, J, 2004)	0.32
" Thus, CGA from GCE is effective in decreasing blood pressure and safe for patients with mild hypertension."	( The blood pressure-lowering effect and safety of chlorogenic acid from green coffee bean extract in essential hypertension. Arai, Y; Kajihara, Y; Kusaura, T; Mitsui, Y; Okawa, W; Saito, I; Watanabe, T, 2006)	0.59
" Based upon this finding, we have attempted to design a novel, effective and safe mucosal vaccine by using CT with several dosages of APE as nasal adjuvants."	( Co-administration of cholera toxin and apple polyphenol extract as a novel and safe mucosal adjuvant strategy. Fujihashi, K; Hagiwara, Y; Inaba, N; Kanno, H; Kobayashi, R; Noda, M; Sato, S; Takahashi, K; Yoshino, N, 2009)	0.35
" However, the precise causes of these adverse reactions are not yet fully understood."	( Role of chlorogenic acid in the toxicity induced by Chinese herbal injections. Dong, X; Fang, SH; Gao, JY; Gu, FM; Li, BQ; Miao, XM; Yang, GQ; Zhang, JX; Zhao, H, 2010)	0.79
" It is obvious that hawthorn, particularly flavonoids constituents with antioxidative activity, reduced the oxidative stress and genotoxicity induced by toxic compounds."	( Protective effect of hawthorn extract against genotoxicity induced by methyl methanesulfonate in human lymphocytes. Azadbakht, M; Hosseinimehr, SJ; Mahmodzadeh, A; Mohammadifar, S; Tanha, M, 2011)	0.37
" Because STLs were detected in both AE and LRE, there is strong evidence that these terpenoids are the main toxic compounds in the leaves of the yacon."	( Renal toxicity caused by oral use of medicinal plants: the yacon example. Da Costa, FB; de Oliveira, RB; de Paula, DA; dos Santos, WF; Franco, JJ; Gobbo-Neto, L; Rocha, BA; Uyemura, SA, 2011)	0.37
" Furthermore, different antioxidant molecules may prevent degeneration induced by the toxic effects of 3-NP."	( Protective effects of chlorogenic acid in 3-nitropropionic acid induced toxicity and genotoxicity. Alarcón-Herrera, N; Ávila-Acevedo, G; Bellido, B; Flores-Maya, S; García-Bores, AM; Hernández-Echeagaray, E; Mendoza, E, 2017)	0.77
"Despite the recurring outbreak of resistance mechanisms and adverse reactions, doxorubicin (Doxo) still remains the standard-of-care for several cancers, including osteosarcoma (OS)."	( Chlorogenic Acid Enhances Doxorubicin-Mediated Cytotoxic Effect in Osteosarcoma Cells. Naviglio, S; Ragone, A; Salzillo, A; Sapio, L; Spina, A, 2021)	2.06

Excerpt	Reference	Relevance
" The disposition of chlorogenic acid at each dose was best fitted to a two-compartment pharmacokinetic model."	( Determination of chlorogenic acid in rat blood by microdialysis coupled with microbore liquid chromatography and its application to pharmacokinetic studies. Chen, CF; Chen, YF; Shum, AY; Tsai, TH, 2000)	0.97
"A simple and sensitive high-performance liquid chromatography (HPLC) method has been developed for the determination of chlorogenic acid (3-O-caffeoyl-D-quinic acid) in plasma and applied to its pharmacokinetic study in rabbits after administration of Flos Lonicerae extract."	( HPLC determination and pharmacokinetics of chlorogenic acid in rabbit plasma after an oral dose of Flos Lonicerae extract. Chen, H; Li, F; Li, L; Yang, H; Yuan, B, 2004)	0.79
" Various potential pharmacodynamic effects have been observed in vitro for mono- and dicaffeoylquinic acids (e."	( Bioavailability and pharmacokinetics of caffeoylquinic acids and flavonoids after oral administration of Artichoke leaf extracts in humans. Derendorf, H; Drewelow, B; Müller, SC; Ploch, M; Veit, M; Windeck, T; Wittemer, SM, 2005)	0.33
" The method was successfully applied to the pharmacokinetic study of CGA in Yin-Huang granules."	( Determination and pharmacokinetic study of chlorogenic acid in rat dosed with Yin-Huang granules by RP-HPLC. Chen, XG; Han, FJ; Hu, ZD; Li, HS; Li, XP; Luo, JY; Yu, J, 2006)	0.6
" This assay has been successfully applied in the pharmacokinetic study of chlorogenic acid and baicalin in vivo through intravenous administration of Yinhuang injection to rats."	( Gradient high-performance liquid chromatography for the simultaneous determination of chlorogenic acid and baicalin in plasma and its application in the study of pharmacokinetics in rats. Deng, L; Fu, Y; Gao, R; Gong, T; Zhang, ZR; Zheng, Q, 2007)	0.79
" This method was validated for specificity, accuracy and precision and was successfully applied to the pharmacokinetic study of syringin and chlorogenic acid in rat plasma after intravenous administration of Aidi lyophilizer."	( Determination and pharmacokinetic study of syringin and chlorogenic acid in rat plasma after administration of Aidi lyophilizer. Bi, KS; Jia, Y; Li, Q; Shen, ZD; Sun, LX; Wang, ZW; Xu, L, 2006)	0.78
" The pharmacokinetic profile of ChA in dog after an intravenous injection was best described by a two-compartment model."	( Pharmacokinetics and excretion of chlorogenic acid in beagle dogs. Liu, J; Ren, X; Xu, XP; Zhang, J; Zhong, S; Zhou, S, 2008)	0.63
" The method was successfully applied to a pharmacokinetic study in rats after an intragastric administration of echinacoside (100 mg/kg)."	( A sensitive and specific liquid chromatography/tandem mass spectrometry method for determination of echinacoside and its pharmacokinetic application in rats. Dai, L; Hao, H; Jiang, Y; Tu, P; Wang, G; Wang, Q; Wang, Y; Yang, H; Zhang, Y; Zheng, C, 2009)	0.35
" The method was successfully applied to a pharmacokinetic study of Mailuoning injection in 10 healthy volunteers."	( Liquid chromatograph/tandem mass spectrometry assay for the simultaneous determination of chlorogenic acid and cinnamic acid in plasma and its application to a pharmacokinetic study. Chen, M; Chu, J; Ju, W; Liu, S; Wu, T; Xu, M; Zhang, J, 2010)	0.58
" The validated method was applied to a comparative pharmacokinetic study in rats after administration of Shuang-huang-lian solutions via intravenous, peroral or intratracheal routes."	( An LC-MS/MS method for the simultaneous determination of chlorogenic acid, forsythiaside A and baicalin in rat plasma and its application to pharmacokinetic study of shuang-huang-lian in rats. Chang, Q; Liao, YH; Liu, CY; Quan, LH; Wei, W; Ye, JX, 2010)	0.61
" The method was validated in terms of selectivity, linearity and sensitivity, and shows advantages in monitoring the pharmacokinetic behaviors of these three compounds."	( Pharmacokinetic study of major bioactive components in rats after oral administration of extract of Ilex hainanensis by high-performance liquid chromatography/electrospray ionization mass spectrometry. Chen, LH; Chen, XQ; Cui, WX; Lv, F; Wang, Q; Wen, XD; Yang, J, 2013)	0.39
" In this research, a comparative study was conducted to compare the pharmacokinetic difference of chlorogenic acid (ChA) after oral administration of LJF and SHL to normal and febrile rats with approximately the same dose of 60 mg/kg, and the antipyrexia effect of LJF and SHL on rectal temperature changes induced by Baker's yeast was investigated."	( Comparative pharmacokinetic study of chlorogenic acid after oral administration of Lonicerae Japonicae Flos and Shuang-Huang-Lian in normal and febrile rats. Gao, R; Gao, Y; Liang, G; Lin, Y; Yu, B, 2014)	0.89
" Chlorogenic acid-derived metabolites were found to be separated into two groups showing different pharmacokinetic properties."	( Bioappearance and pharmacokinetics of bioactives upon coffee consumption. Beusch, A; Dieminger, N; Dunkel, A; Hauner, H; Hofmann, T; Lang, R; Lee, YM; Skurk, T; Suess, B; Wahl, A, 2013)	1.3
" Therefore, pharmacokinetic studies of the caffeoylquinic acids are needed."	( A rapid and sensitive UPLC-MS/MS method for quantification of two caffeoylquinic acids and four main active components in rat plasma after an intravenous administration of Qingkailing injection and its application to a pharmacokinetic study. Gao, X; Guo, M; Liu, H; Peng, L; Song, Y; Su, J; Zhang, L; Zhao, L, 2014)	0.4
"Few studies describing the pharmacokinetic properties of chlorogenic acid (CA) and corydaline (CRD) which are marker compounds of a new prokinetic botanical agent, DA-9701, have been reported."	( Pharmacokinetics of chlorogenic acid and corydaline in DA-9701, a new botanical gastroprokinetic agent, in rats. Jeong, JS; Jung, JW; Kang, HE; Kim, JM; Lee, HS; Lee, MG; Son, M, 2014)	0.97
" The validated method was successfully applied to a pharmacokinetic study of the four bioactive components in rats after intravenous administration of Reduning injection."	( Simultaneous determination of neochlorogenic acid, chlorogenic acid, cryptochlorogenic acid and geniposide in rat plasma by UPLC-MS/MS and its application to a pharmacokinetic study after administration of Reduning injection. Fu, X; Li, F; Wang, Y; Wang, Z; Wen, J; Xiao, W; Xiong, Z; Zhao, L; Zheng, W, 2015)	0.7
"To study on the effects of Achyranthes bidentata on Tongsaimai pellets main active ingredients chlorogenic acid, isoliquiritin, harpagoside and glycyrrhizin in rats in vivo pharmacokinetic behaviors, a method for the simultaneous determination of chlorogenic acid, isoliquiritin, harpagoside and liquiritigenin in rat plasma was established by UPLC-MS/MS."	( [Studies on effects of Achyranthes bidentata on tongsaimai pellets main active ingredients chlorogenic acid, isoliquiritin, harpagoside and glycyrrhizin in vivo pharmacokinetics]. Bi, XL; Cheng, J; Di, LQ; Kang, A; Li, JS; Shan, JJ; Zhao, XL, 2014)	0.84
" This study provided the pharmacokinetic profiles and the tissue regional distribution of MCQAs, DCQAs and caffeic acid."	( Comparative pharmacokinetics and tissue distribution study of mono-, and di-caffeoylquinic acids isomers of Ainsliaea fragrans Champ by a fast UHPLC-MS/MS method. Feng, Y; Huang, J; Song, Y; Su, D, 2014)	0.4
" We conducted a phase I and pharmacokinetic study with the phenolic compound-enriched product extracted from Erigeron breviscapus, Erigerontis hydroxybenzenes injection (EHI), in healthy Chinese volunteers."	( Clinical tolerability and pharmacokinetics of Erigerontis hydroxybenzene injection: results of a randomized phase I study in healthy Chinese volunteers. Dai, GL; Fang, ZY; Ju, WZ; Liu, F; Liu, SJ; Wu, T; Xiong, NN; Zhang, J; Zhao, Y; Zhou, L, 2015)	0.42
" The method validation results demonstrated that the proposed method was sensitive, specific, and reliable, which was successfully applied to the pharmacokinetic study of four components after oral administration of Echinacea purpurea extract."	( Simultaneous determination and pharmacokinetic study of four phenol compounds in rat plasma by ultra-high performance liquid chromatography with tandem mass spectrometry after oral administration of Echinacea purpurea extract. Du, Y; Gan, C; Gao, M; Liu, L; Wang, L; Wu, L; Yang, C, 2016)	0.43
" However, its pharmacokinetic properties and bioavailability remained unresolved."	( Pharmacokinetics of isochlorgenic acid C in rats by HPLC-MS: Absolute bioavailability and dose proportionality. Cen, MF; Cheng, XG; Huang, LH; Wang, GX; Wang, SJ; Xiong, XH; Zang, LQ; Zhong, YM, 2016)	0.43
" The regression analysis of AUC(0-∞) and Cmax at the three doses (5, 10 and 25mgkg(-1)) indicated that the equations were y=35."	( Pharmacokinetics of isochlorgenic acid C in rats by HPLC-MS: Absolute bioavailability and dose proportionality. Cen, MF; Cheng, XG; Huang, LH; Wang, GX; Wang, SJ; Xiong, XH; Zang, LQ; Zhong, YM, 2016)	0.43
" Bioavailability of IAC in rats was poor and both Cmax and AUC(0-∞) of IAC had a positive correlation with dose."	( Pharmacokinetics of isochlorgenic acid C in rats by HPLC-MS: Absolute bioavailability and dose proportionality. Cen, MF; Cheng, XG; Huang, LH; Wang, GX; Wang, SJ; Xiong, XH; Zang, LQ; Zhong, YM, 2016)	0.43
" It was successfully applied to a pharmacokinetic study of CGA and TCA in healthy Chinese volunteers after oral administration of Shuanghua Baihe tablets (SBTs)."	( Simultaneous quantification of chlorogenic acid and taurocholic acid in human plasma by LC-MS/MS and its application to a pharmacokinetic study after oral administration of Shuanghua Baihe tablets. Cheng, ML; Ding, L; Gu, P; Liu, RJ; Liu, YJ; Ma, PC; Wu, Y; Zheng, L, 2016)	0.72
" The pharmacokinetic parameters of the 3,4-, 3,5- and 4,5- DCQA were remarkably different from those in normal rats."	( Simultaneous determination of three di-caffeoylquinic acids by UHPLC-MS/MS in rat plasma and its application to a comparative pharmacokinetic study in normal and acute lung injury rat. Ma, C; Wang, Y; Wu, X; Xiao, W; Xiong, Z, 2017)	0.46
" The validated method was successfully applied to pharmacokinetic study of isochlorogenic acid A in rats for the first time."	( Development and Validation of a HPLC Method for Determination of Isochlorogenic Acid A in Rat Plasma and Application to Pharmacokinetic Study. Cen, M; Cheng, X; Liang, H; Wang, S; Xiong, X; Zeng, J, 2017)	0.92
"In order to research and enhance bioavailability of chlorogenic acid and rutin(CA-R) via the oral route, chitosan coated composite phospholipid liposomes (C-CPLs) were applied to study on preparation, permeability and pharmacokinetic of C-CA-R-CPLs."	( Chitosan coated chlorogenic acid and rutincomposite phospholipid liposomes: Preparation, characterizations, permeability and pharmacokinetic. He, C; Jiang, W; Li, J; Xing, J; Zeng, C; Zheng, R, 2018)	1.08
" This method was successfully applied to pharmacokinetic study of CGA in Chinese subjects with advanced solid tumor after intramuscular injection administration of Chlorogenic acid for injection (CAFI)."	( Development of an LC-MS/MS method for quantitative analysis of Chlorogenic acid in human plasma and its application to a pharmacokinetic study in Chinese patients with advanced solid tumor. Bing Xu, G; Gao, J; Gong, JF; Kou, FR; Li, Y; Shen, L; Yang, F; Zhang, C, 2020)	0.99
" 4 software was used to fit pharmacokinetic parameters."	( [Simultaneous determination of four components of Shuganning Injection in rat plasma by UPLC-MS/MS and its application to a pharmacokinetic study]. Gong, ZP; He, F; Hu, HJ; Kang, NF; Li, M; Li, Y; Li, YT; Liu, LQ; Wang, AM; Wang, YL; Xiao, HQ; Zhang, Y, 2020)	0.56
" Nevertheless, no study has been performed on the exposure differences of the pharmacodynamic material basis in vivo caused by different extraction methods."	( Integrated metabolism, network pharmacology, and pharmacokinetics to explore the exposure differences of the pharmacodynamic material basis in vivo caused by different extraction methods for Saussurea involucrata. Chen, B; Liu, M; Lyu, H; Ma, C; Tu, S; Wu, C; Xu, X; Yang, L; Yiming, A, 2022)	0.72
"Based on the integrated strategy of metabolism, network pharmacology, and pharmacokinetics, we aimed to reveal exposure differences in pharmacodynamic substances caused by different extraction methods."	( Integrated metabolism, network pharmacology, and pharmacokinetics to explore the exposure differences of the pharmacodynamic material basis in vivo caused by different extraction methods for Saussurea involucrata. Chen, B; Liu, M; Lyu, H; Ma, C; Tu, S; Wu, C; Xu, X; Yang, L; Yiming, A, 2022)	0.72
" Twenty-three prototype components were analyzed by network pharmacology, and seven critical active components were selected as representative markers for the pharmacokinetic study."	( Integrated metabolism, network pharmacology, and pharmacokinetics to explore the exposure differences of the pharmacodynamic material basis in vivo caused by different extraction methods for Saussurea involucrata. Chen, B; Liu, M; Lyu, H; Ma, C; Tu, S; Wu, C; Xu, X; Yang, L; Yiming, A, 2022)	0.72
" This research aimed to provide the basis of metabolism in vivo for further studying these pharmacodynamic differences."	( Integrated metabolism, network pharmacology, and pharmacokinetics to explore the exposure differences of the pharmacodynamic material basis in vivo caused by different extraction methods for Saussurea involucrata. Chen, B; Liu, M; Lyu, H; Ma, C; Tu, S; Wu, C; Xu, X; Yang, L; Yiming, A, 2022)	0.72
"The present study investigated the pharmacodynamic material basis of Laportea bulbifera in the treatment of rheumatoid arthritis."	( [Potential pharmacodynamic substances of Laportea bulbifera in treatment of rheumatoid arthritis based on serum pharmacochemistry and pharmacology]. Chen, SY; Chen, Y; Gong, ZP; Huang, Y; Lan, YY; Li, YT; Tang, J; Wang, YL; Wu, D; Zhang, Q; Zheng, L, 2022)	0.72

Excerpt	Reference	Relevance
"The present study analyses the effect of two plant phenolic compounds, namely chlorogenic acid and ferulic acid, and a plant alkaloid, berberine, alone and also in combination with two commercial oral hypoglycemic drugs (OHD), namely metformin and 2,4-thiazolodinedione (THZ), on the uptake of 2-deoxyglucose (2DG) by L6 myotubes."	( Synergistic effect of phytochemicals in combination with hypoglycemic drugs on glucose uptake in myotubes. Doble, M; Prabhakar, PK, 2009)	0.58
" Here, we developed an effective strategy, typical ultraviolet (UV) spectra in combination with diagnostic mass fragmentation analysis based on HPLC-DAD-QTOF-MS/MS, to comprehensively profile CGA in the buds of Lonicera macranthoides."	( Typical ultraviolet spectra in combination with diagnostic mass fragmentation analysis for the rapid and comprehensive profiling of chlorogenic acids in the buds of Lonicera macranthoides. Cai, P; Chen, L; Chen, W; Hu, X; Huang, LQ; Shi, SY; Zhang, SH, 2016)	0.64
" Microdialysis combined with liquid chromatography coupled to quadrupole time-of-flight tandem mass spectrometry (LC/QTOF-MS/MS) was established for the purpose of screening of the multiple bioactive compounds in traditional Chinese medicines (TCMs)."	( Characterization of interaction property of multi-components in Gardenia jasminoides with aldose reductase by microdialysis combined with liquid chromatography coupled to mass spectrometry. Liu, S; Liu, Z; Song, F; Wang, L; Xing, J, 2016)	0.43
" However, drug-drug Interactions (DDIs) between DCQAs and possible concomitant drugs were not fully understood in clinic."	( Organic anion transporter 3 (OAT3)-mediated transport of dicaffeoylquinic acids and prediction of potential drug-drug interaction. Deng, S; Feng, L; Huo, X; Lin, Y; Ma, X; Ren, J; Sun, C; Sun, Q; Tian, X; Wang, C; Wang, Y; Zhang, B; Zhang, Z, 2019)	0.51
"Near-infrared spectroscopy (NIRS) combined with chemometrics was used to analyze the main active ingredients including chlorogenic acid, caffeic acid, luteoloside, baicalin, ursodesoxycholic acid, and chenodeoxycholic acid in the Tanreqing injection."	( Rapid analysis of the Tanreqing injection by near-infrared spectroscopy combined with least squares support vector machine and Gaussian process modeling techniques. Li, W; Liu, S; Pan, J; Qu, H; Xue, D; Yan, X, 2019)	0.72
" 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)	0.56
" A novel comprehensive and effective approach to mine trace unknown compounds combined with structure recognition in complex matrix is developed, in order to profiling potential Chlorogenic acids (CGAs) in Lonicera Flos (LFs): using multiple neutral loss/precursor ion (NL/PI) markers scans combined with high resolution mass spectrometry (HRMS)."	( Multi-marker scans coupled to high-resolution mass spectrometry strategy for global profiling combined with structure recognition of unknown trace chlorogenic acids in Lonicera Flos. Chen, F; Duan, X; Feng, F; Feng, X; Liu, T; Wang, E; Wu, H; Zhang, F, 2021)	1.01
"The antibacterial and antibiofilm mechanisms of ultrasound combined with chlorogenic acid treatment for Salmonella enteritidis under biofilm and planktonic condition were investigated."	( Contribution of ultrasound in combination with chlorogenic acid against Salmonella enteritidis under biofilm and planktonic condition. Liu, F; Sun, J; Sun, Z; Wang, D, 2022)	1.21
"This study employed Box-Behnken design combined with flux attenuation to explore the nanofiltration conditions for separation of alcohol precipitation liquid during the preparation of Reduning Injection and discussed the applicability of nanofiltration in the separation of the liquid with high-concentration ethanol."	( [Exploration of nanofiltration conditions for separation of alcohol precipitation liquid during preparation of Reduning Injection by Box-Behnken design combined with flux attenuation]. Jiang, JL; Li, CY; Peng, GP; Zhang, YT; Zhi, XL; Zou, YC, 2022)	0.72
" In conclusion, CGA in combination with EGCG ameliorated the gut alterations induced by aging, in part, through antioxidant and anti-inflammatory effects, along with its gut microbiota modulatory capacity."	( Chlorogenic acid combined with epigallocatechin-3-gallate mitigates D-galactose-induced gut aging in mice. Mackenzie, GG; Su, Z; Wei, R, 2023)	2.35

Excerpt	Reference	Relevance
" The study described here has investigated the bioavailability of ferulic acid in humans, from tomato consumption, through the monitoring of the pharmacokinetics of excretion in relation to intake."	( Bioavailability of ferulic acid. Bourne, LC; Rice-Evans, C, 1998)	0.3
" These results suggest that chlorogenic acid is not well absorbed from the digestive tract, unlike caffeic acid, and subject to almost no structural changes to the easily absorbed forms."	( Absorption of chlorogenic acid and caffeic acid in rats after oral administration. Azuma, K; Higashio, H; Ippoushi, K; Ito, H; Nakayama, M; Terao, J, 2000)	0.96
" To the best of our knowledge, this is the first study demonstrating naringenin bioavailability in humans after consumption of a meal containing cooked tomato paste."	( Naringenin from cooked tomato paste is bioavailable in men. Bugianesi, R; Catasta, G; D'Uva, A; Maiani, G; Spigno, P, 2002)	0.31
" However, adequate intakes and absorption rate of phenolic compounds are necessary for these beneficial effects."	( Influence of cooking process on phenolic marker compounds of vegetables. Andlauer, W; Fürst, P; Hubert, M; Rings, A; Stumpf, C, 2003)	0.32
" Such a high abundance of microbial metabolites shows that the bioavailability of chlorogenic acid depends largely on its metabolism by the gut microflora."	( Chlorogenic acid bioavailability largely depends on its metabolism by the gut microflora in rats. Besson, C; Gonthier, MP; Rémésy, C; Scalbert, A; Verny, MA, 2003)	1.99
" The bioavailability of these compounds is an essential requirement to sustain their in vivo role."	( Effect of domestic cooking on human bioavailability of naringenin, chlorogenic acid, lycopene and beta-carotene in cherry tomatoes. Azzini, E; Bugianesi, R; Catasta, G; Ferracane, R; Leonardi, C; Maiani, G; Salucci, M, 2004)	0.56
"This investigation was carried out to evaluate the effect of domestic cooking on the bioavailability in humans of antioxidant molecules after the administration of a test meal containing cherry tomatoes."	( Effect of domestic cooking on human bioavailability of naringenin, chlorogenic acid, lycopene and beta-carotene in cherry tomatoes. Azzini, E; Bugianesi, R; Catasta, G; Ferracane, R; Leonardi, C; Maiani, G; Salucci, M, 2004)	0.56
" Considering that both naringenin and chlorogenic acid are widely studied for their potential healthy properties, evidence of their bioavailability and of the factors influencing their bioaccessibility is an important tool to sustain the possibility that these polyphenols play a biological role in human physiology."	( Effect of domestic cooking on human bioavailability of naringenin, chlorogenic acid, lycopene and beta-carotene in cherry tomatoes. Azzini, E; Bugianesi, R; Catasta, G; Ferracane, R; Leonardi, C; Maiani, G; Salucci, M, 2004)	0.83
" Thus, HHQ-free coffee might regulate vascular tone by improving the bioavailability of nitric oxide in SHR."	( Improvement of hypertension and vascular dysfunction by hydroxyhydroquinone-free coffee in a genetic model of hypertension. Fujii, A; Kameyama, A; Nishizawa, Y; Ohminami, H; Saito, I; Shibuya, Y; Suzuki, A; Tokimitsu, I; Yamamoto, M; Yamamoto, N, 2006)	0.33
"The bioavailability of chlorogenic acid, a major polyphenol of the human diet that is particularly abundant in coffee and various fruits, was explored in rats."	( Chlorogenic acid is absorbed in its intact form in the stomach of rats. Besson, C; Gil-Izquierdo, A; Lafay, S; Manach, C; Morand, C; Scalbert, A, 2006)	2.09
"Dietary CQA reduces oxidative stress and improves nitric oxide bioavailability by inhibiting excessive production of reactive oxygen species in the vasculature, and leads to the attenuation of endothelial dysfunction, vascular hypertrophy, and hypertension in spontaneously hypertensive rats."	( Chlorogenic acid attenuates hypertension and improves endothelial function in spontaneously hypertensive rats. Fujii, A; Jokura, H; Saito, I; Suzuki, A; Tokimitsu, I; Yamamoto, M; Yamamoto, N, 2006)	1.78
" Their bioavailability therefore appears to be governed largely by their uptake into the gut mucosa."	( Absorption and metabolism of caffeic acid and chlorogenic acid in the small intestine of rats. Besson, C; Lafay, S; Manach, C; Morand, C; Scalbert, A, 2006)	0.59
" CQA absorption and bioavailability were then studied in vitro using a Caco-2 cell model coupled with an in vitro digestion process, and in vivo, in a chronic supplementation study in which rats were fed daily coffee or coffee and milk for 3 weeks."	( Chlorogenic acid is poorly absorbed, independently of the food matrix: A Caco-2 cells and rat chronic absorption study. Dupas, C; Maillard, MN; Marsset Baglieri, A; Ordonaud, C; Tomé, D, 2006)	1.78
" Several studies have shown the effect on animal models of artichoke extracts, while information on human bioavailability and metabolism of hydroxycinnamates derivatives is still lacking."	( Absorption and metabolism of bioactive molecules after oral consumption of cooked edible heads of Cynara scolymus L. (cultivar Violetto di Provenza) in human subjects: a pilot study. Azzini, E; Bugianesi, R; Catasta, G; Di Venere, D; Durazzo, A; Foddai, MS; Linsalata, V; Maiani, G; Miccadei, S; Romano, F, 2007)	0.34
" Despite the potential biopharmacological properties attributed to these compounds, little is known about their bioavailability in humans."	( Chlorogenic acid compounds from coffee are differentially absorbed and metabolized in humans. Donangelo, C; Farah, A; Monteiro, M; Perrone, D; Trugo, LC, 2007)	1.78
" Absorption rate constants were determined by the plot of log remaining amount of drug in perfusate vs."	( Absorptive profile of chlorogenic acid in rats. Chen, Z; Jiang, X; Li, C; Li, K; Ma, G; Ren, J, 2007)	0.65
" However, data on the bioavailability of CGA from green coffee in humans are inexistent."	( Chlorogenic acids from green coffee extract are highly bioavailable in humans. Donangelo, CM; Farah, A; Lafay, S; Monteiro, M, 2008)	1.79
" Central to this opportunity is a need to better understand factors that may affect the bioavailability of specific phenolic components from coffee and tea based beverages."	( The influence of beverage composition on delivery of phenolic compounds from coffee and tea. Ferruzzi, MG, 2010)	0.36
" However, their high hydrophilicity results in a poor bioavailability hindering the development of efficient antioxidant strategies."	( Does hydrophobicity always enhance antioxidant drugs? A cut-off effect of the chain length of functionalized chlorogenate esters on ROS-overexpressing fibroblasts. Cabello, G; Chabi, B; Laguerre, M; Lecomte, J; López Giraldo, LJ; Villeneuve, P; Wrutniak-Cabello, C, 2011)	0.37
"Different studies have shown that milk may interact with polyphenols and affect their bioavailability in humans."	( Effect of simultaneous consumption of milk and coffee on chlorogenic acids' bioavailability in humans. Duarte, GS; Farah, A, 2011)	0.61
" In future, this analytical method will give more confidence in compound identification to provide a more comprehensive assessment of coffee polyphenol bioavailability studies in humans."	( Identification of novel circulating coffee metabolites in human plasma by liquid chromatography-mass spectrometry. Dionisi, F; Guy, P; Nagy, K; Redeuil, K; Renouf, M; Rezzi, S; Smarrito-Menozzi, C; Williamson, G, 2011)	0.37
" In conclusion, hydrolysis of the extract of Ilex paraguariensis is a strategy to improve its bioavailability and in vivo antioxidant activity."	( Hydrolysis influence on phytochemical composition, antioxidant activity, plasma concentration, and tissue distribution of hydroethanolic Ilex paraguariensis extract components. Almeida, RL; Barros, SB; Rivelli, DP; Ropke, CD, 2011)	0.37
" The absorption rate constant K(a) and the hourly absorption percentages A were essentially unchanged."	( [Study on in situ intestinal absorption of active ingredients in Shuanghuanglian oral liquid in rats]. Bi, X; Chen, L; Di, L; Du, Q; Zhou, W, 2011)	0.37
" Mechanistically, the metabolites of CGAs attenuate oxidative stress (reactive oxygen species), which leads to the benefit of blood-pressure reduction through improved endothelial function and nitric oxide bioavailability in the arterial vasculature."	( Antihypertensive effects and mechanisms of chlorogenic acids. Ballevre, O; Luo, H; Wang, J; Zhang, W; Zhao, Y, 2012)	0.64
"This paper reviews recent human studies on the bioavailability of chlorogenic acids in coffee and green tea flavan-3-ols in which the identification of metabolites, catabolites and parent compounds in plasma, urine and ileal fluid was based on mass spectrometric methodology."	( Bioavailability of coffee chlorogenic acids and green tea flavan-3-ols. Calani, L; Crozier, A; Del Rio, D; Stalmach, A, 2010)	0.9
" The CGA is well absorbed orally, and its effects on gastric ulcer have not been previously reported."	( Antiulcerogenic activity of chlorogenic acid in different models of gastric ulcer. de Melo, IL; de Oliveira e Silva, AM; Farsky, SH; Machado, ID; Mancini-Filho, J; Santin, JR; Shimoyama, AT, 2013)	0.68
" Meanwhile, the combined formula SHL exhibits higher bioavailability of ChA and superior antipyrexia effect than the single herb."	( Comparative pharmacokinetic study of chlorogenic acid after oral administration of Lonicerae Japonicae Flos and Shuang-Huang-Lian in normal and febrile rats. Gao, R; Gao, Y; Liang, G; Lin, Y; Yu, B, 2014)	0.68
" This study is one of a series with the aim of determining possible effects of food matrices on caffeoylquinic acid (CQA) bioavailability using ileostomy volunteers."	( Absorption and isomerization of caffeoylquinic acids from different foods using ileostomist volunteers. Erk, T; Melcher, R; Renouf, M; Richling, E; Steiling, H; Williamson, G, 2014)	0.4
"Our results show that variations in food matrices and variations in phenolic composition have a major influence on intestinal bioavailability and interesterification of the investigated subclass of polyphenols, the CQAs."	( Absorption and isomerization of caffeoylquinic acids from different foods using ileostomist volunteers. Erk, T; Melcher, R; Renouf, M; Richling, E; Steiling, H; Williamson, G, 2014)	0.4
" Thus, specific data on their bioavailability in the upper gastrointestinal tract are of high interest, since some molecules are absorbed here and so are not metabolized by colonic microflora."	( Structure- and dose-absorption relationships of coffee polyphenols. Dionisi, F; Erk, T; Hauser, J; Renouf, M; Richling, E; Steiling, H; Williamson, G, )	0.13
" Since piperine is known to enhance curcumin bioavailability to more than two thousand times by inhibiting its efflux, a conjugate of curcumin-piperic acid was also used."	( Human papilloma virus 16 E6 protein as a target for curcuminoids, curcumin conjugates and congeners for chemoprevention of oral and cervical cancers. Misra, K; Singh, AK, 2013)	0.39
" Pathways involved in colonic catabolism of CGAs are proposed and comparison with studies on the bioavailability of coffee CGAs ingested by humans helped distinguish between colonic catabolites and phase II metabolites of CGAs."	( Catabolism of coffee chlorogenic acids by human colonic microbiota. Alan, C; Concepción, C; Ludwig, IA; Paz de Peña, M, )	0.45
" Even though coffee intake has been associated with some health benefits in epidemiological studies, the bioavailability of coffee phenolics is not fully understood."	( Dose-response plasma appearance of coffee chlorogenic and phenolic acids in adults. Barron, D; Beaumont, M; Dionisi, F; Giuffrida, F; Lepage, M; Marmet, C; Renouf, M; Williamson, G, 2014)	0.4
"We performed a dose-response study measuring plasma bioavailability of phenolics after drinking three increasing, but still nutritionally relevant doses of instant pure soluble coffee."	( Dose-response plasma appearance of coffee chlorogenic and phenolic acids in adults. Barron, D; Beaumont, M; Dionisi, F; Giuffrida, F; Lepage, M; Marmet, C; Renouf, M; Williamson, G, 2014)	0.4
" CGAs were not well absorbed in their intact form, regardless of the dose."	( Dose-response plasma appearance of coffee chlorogenic and phenolic acids in adults. Barron, D; Beaumont, M; Dionisi, F; Giuffrida, F; Lepage, M; Marmet, C; Renouf, M; Williamson, G, 2014)	0.4
"This study confirmed previous findings about coffee bioavailability but also showed that coffee phenolics appear in a positive dose-response manner in plasma when drank at nutritionally relevant doses."	( Dose-response plasma appearance of coffee chlorogenic and phenolic acids in adults. Barron, D; Beaumont, M; Dionisi, F; Giuffrida, F; Lepage, M; Marmet, C; Renouf, M; Williamson, G, 2014)	0.4
" Incomplete absorption of CA, its decomposition in the gastrointestinal tract, and/or pre-systemic metabolism resulted in extremely low oral bioavailability (F) of CA (0."	( Pharmacokinetics of chlorogenic acid and corydaline in DA-9701, a new botanical gastroprokinetic agent, in rats. Jeong, JS; Jung, JW; Kang, HE; Kim, JM; Lee, HS; Lee, MG; Son, M, 2014)	0.73
" 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
" At the concentrations of 20 to 80 microg x mL(-1), the difference of absorption rate constants (K(a)) was not statistically significant."	( [Enhancers on the transmembrane transport of chlorogenic acid]. Deng, SQ; Jiang, XH; Ren, J; Wang, LL; Xiao, Y, 2014)	0.66
" It was found that bergenin and chlorogenic acid had typical extravascular administration concentration-time curves; flavonoids had a bimodal distribution improving bioavailability and extending the pharmacodynamics period."	( An LC-MS/MS method for the simultaneous determination and pharmacokinetic studies of bergenin, chlorogenic acid and four flavonoids in rat plasma after oral administration of a QingGanSanJie decotion extract. Chai, Y; Li, W; Lv, L; Qian, X; Zhang, G; Zhang, H; Zhao, L, 2014)	0.9
" Peak plasma concentration and urinary excretion values showed trends towards a reduced bioavailability of chlorogenic acids associated with the highest dose ingested, when expressed as percentages of intake."	( Impact of dose on the bioavailability of coffee chlorogenic acids in humans. Crozier, A; Stalmach, A; Williamson, G, 2014)	0.87
" The bioavailability and the distribution of each compound and its metabolites also contribute to coffee mechanisms of action."	( Coffee components and cardiovascular risk: beneficial and detrimental effects. Buscemi, S; Galvano, F; Godos, J; Grosso, G; Li Volti, G; Marventano, S; Pluchinotta, FR, 2014)	0.4
" In this study, the potential for bioavailability of the artichoke polyphenols was estimated by using both in vitro digestion and Caco-2 human intestinal cell models."	( Polyphenols from artichoke heads (Cynara cardunculus (L.) subsp. scolymus Hayek): in vitro bio-accessibility, intestinal uptake and bioavailability. Cardinali, A; D'Antuono, I; Garbetta, A; Linsalata, V; Minervini, F, 2015)	0.42
" Moreover, an in vitro gastrointestinal digestion model, applied to determine the effect of processing on the bioavailability of mulberry antioxidants, indicated a higher anthocyanin bioavailability for the fruit matrix than for the juice matrix."	( The effects of juice processing on black mulberry antioxidants. Beekwilder, J; Boyacioglu, D; Capanoglu, E; Hall, R; Tomas, M; Toydemir, G, 2015)	0.42
"The present work was aimed at developing an optimized oral nanostructured lipid carrier (NLC) formulation of poorly soluble atorvastatin Ca (AT Ca) and assessing its in vitro release, oral bioavailability and pharmacodynamic activity."	( Chlorogenic acid stabilized nanostructured lipid carriers (NLC) of atorvastatin: formulation, design and in vivo evaluation. Ali, J; Baboota, S; Khan, S; Narang, JK; Narang, RS, 2016)	1.88
" Isolation and identification of these metabolites may be used as references for in vivo bioavailability experiments and for investigating their bioactivity in in vitro experiments."	( Development and Validation of an in vitro Experimental GastroIntestinal Dialysis Model with Colon Phase to Study the Availability and Colonic Metabolisation of Polyphenolic Compounds. Bosscher, D; Breynaert, A; Claeys, M; Cos, P; Hermans, N; Kahnt, A; Pieters, L, 2015)	0.42
"Although ingestion of coffee and its constituent chlorogenic acid (CGA) protects the retina from oxidative stress, the bioaccessibility and bioavailability of coffee metabolites are not well understood."	( Effects of phenolic acid metabolites formed after chlorogenic acid consumption on retinal degeneration in vivo. Ahn, HR; Choi, Y; Jang, H; Jung, SH; Lee, CY, 2015)	0.92
"We evaluated the bioavailability of chlorogenic acids (CGAs) in 2 coffees and the effects of their consumption on the plasma antioxidant capacity (AC), the serum lipid profile, and the vascular function in healthy adults."	( Coffee Consumption Increases the Antioxidant Capacity of Plasma and Has No Effect on the Lipid Profile or Vascular Function in Healthy Adults in a Randomized Controlled Trial. Agudelo-Ochoa, GM; Duque-Ramírez, M; Lara-Guzmán, OJ; Muñoz-Durango, K; Naranjo-Cano, M; Pulgarín-Zapata, IC; Quintero-Ortiz, MM; Velásquez-Rodriguez, CM, 2016)	0.71
"In the present study, a formulation system consisting of cholesterol and phosphatidyl choline was used to prepare an effective chlorogenic acid-loaded liposome (CAL) with an improved oral bioavailability and an increased antioxidant activity."	( Enhanced oral bioavailability and in vivo antioxidant activity of chlorogenic acid via liposomal formulation. Feng, Y; Firempong, CK; Omari-Siaw, E; Pu, Z; Sun, C; Wan, J; Xu, X; Xu, Y; Yu, J; Yuan, Y; Zhu, Y, 2016)	0.88
"Understanding the bioavailability and metabolism of coffee compounds will contribute to identify the unknown biological mechanism(s) linked to their beneficial effects."	( The roasting process does not influence the extent of conjugation of coffee chlorogenic and phenolic acids. Actis-Goretta, L; Beaumont, M; Renouf, M; Sanchez-Bridge, B; Sauser, J, 2016)	0.43
" However, its pharmacokinetic properties and bioavailability remained unresolved."	( Pharmacokinetics of isochlorgenic acid C in rats by HPLC-MS: Absolute bioavailability and dose proportionality. Cen, MF; Cheng, XG; Huang, LH; Wang, GX; Wang, SJ; Xiong, XH; Zang, LQ; Zhong, YM, 2016)	0.43
"To determine the absolute bioavailability in rats and the dose proportionality on the pharmacokinetics of single oral dose of IAC."	( Pharmacokinetics of isochlorgenic acid C in rats by HPLC-MS: Absolute bioavailability and dose proportionality. Cen, MF; Cheng, XG; Huang, LH; Wang, GX; Wang, SJ; Xiong, XH; Zang, LQ; Zhong, YM, 2016)	0.43
" Absolute bioavailability in rats was determined by comparing pharmacokinetic data after administration of single oral (5, 10 and 25mgkg(-1)) and intravenous (5mgkg(-1)) doses of IAC."	( Pharmacokinetics of isochlorgenic acid C in rats by HPLC-MS: Absolute bioavailability and dose proportionality. Cen, MF; Cheng, XG; Huang, LH; Wang, GX; Wang, SJ; Xiong, XH; Zang, LQ; Zhong, YM, 2016)	0.43
"Experimental data showed that absolute oral bioavailability of IAC in rats across the doses ranged between 14."	( Pharmacokinetics of isochlorgenic acid C in rats by HPLC-MS: Absolute bioavailability and dose proportionality. Cen, MF; Cheng, XG; Huang, LH; Wang, GX; Wang, SJ; Xiong, XH; Zang, LQ; Zhong, YM, 2016)	0.43
"A new HPLC-MS method was developed to determine the bioavailability and the dose proportionality of IAC."	( Pharmacokinetics of isochlorgenic acid C in rats by HPLC-MS: Absolute bioavailability and dose proportionality. Cen, MF; Cheng, XG; Huang, LH; Wang, GX; Wang, SJ; Xiong, XH; Zang, LQ; Zhong, YM, 2016)	0.43
" In addition, we also discuss its biosynthesis, sources, bioavailability and metabolism, to provide a broad perspective of the therapeutic implications of this compound in brain health and disease."	( Chlorogenic Acid and Mental Diseases: From Chemistry to Medicine. Braidy, N; Daglia, M; Gortzi, O; Manayi, A; Nabavi, SF; Nabavi, SM; Setzer, WN; Sureda, A; Tejada, S, 2017)	1.9
" AN could only be detected in the plasma and liver homogenate of normal mice, which was poorly absorbed in OVX mice and low in other measured tissues."	( Pharmacokinetics and tissue distribution of five active ingredients of Eucommiae cortex in normal and ovariectomized mice by UHPLC-MS/MS. An, J; Hu, F; Wang, C; Wang, Z; Yang, L; Zhang, Z, 2016)	0.43
"The purpose of this study was to develop a self-microemulsifying drug delivery system (SMEDDS) to improve the oral bioavailability of Chlorogenic acid (CA), an important bioactive compound from Lonicerae Japonicae Flos with poor permeability."	( Characterization, pharmacokinetics and tissue distribution of chlorogenic acid-loaded self-microemulsifying drug delivery system. Chen, L; Chen, QZ; Jing, J; Liu, CS; Lv, JJ; Wang, S; Xiong, YA, 2017)	0.9
" The bioavailability of these compounds depends among others on their interactions with other components of the diet, mainly proteins."	( Influence of the Form of Administration of Chlorogenic Acids on Oxidative Stress Induced by High fat Diet in Rats. Budryn, G; Grzelczyk, J; Juśkiewicz, J; Zaczyńska, D; Zduńczyk, Z; Żyżelewicz, D, 2017)	0.72
"The data indicate bioavailability of early and late phase WBB metabolites peaking at different times during the 24 h period, which may be important for maximizing their biological activity."	( Characterization of Wild Blueberry Polyphenols Bioavailability and Kinetic Profile in Plasma over 24-h Period in Human Subjects. Burton-Freeman, B; Edirisinghe, I; Sandhu, A; Zhong, S, 2017)	0.46
" We carried out a randomized crossover pilot clinical trial to evaluate the matrix effect (raw flesh and juice) of 'Ataulfo' mango on the bioavailability of its phenolic compounds."	( Processing 'Ataulfo' Mango into Juice Preserves the Bioavailability and Antioxidant Capacity of Its Phenolic Compounds. Astiazaran-Garcia, H; Blumberg, JB; Chen, CO; González-Aguilar, GA; Quirós-Sauceda, AE; Wall-Medrano, A, 2017)	0.46
" The absolute bioavailability was calculated to be 22."	( Development and Validation of a HPLC Method for Determination of Isochlorogenic Acid A in Rat Plasma and Application to Pharmacokinetic Study. Cen, M; Cheng, X; Liang, H; Wang, S; Xiong, X; Zeng, J, 2017)	0.69
"The bioavailability and oxidative damage toxicity of lead (Pb) in seven food matrices, including rice, milk, tomato, garlic, apple, kelp and pork, were determined using an in vitro digestion/Caco-2 cell model and a rat pheochromocytoma (PC12) oxidative damage model."	( Effect of food matrices on the in vitro bioavailability and oxidative damage in PC12 cells of lead. Fang, Y; Hu, Q; Li, P; Pei, F; Shen, X; Shi, Y; Wu, J; Xia, J; Xie, M, 2018)	0.48
"In order to research and enhance bioavailability of chlorogenic acid and rutin(CA-R) via the oral route, chitosan coated composite phospholipid liposomes (C-CPLs) were applied to study on preparation, permeability and pharmacokinetic of C-CA-R-CPLs."	( Chitosan coated chlorogenic acid and rutincomposite phospholipid liposomes: Preparation, characterizations, permeability and pharmacokinetic. He, C; Jiang, W; Li, J; Xing, J; Zeng, C; Zheng, R, 2018)	1.08
" The alkaloids caffeine and trigonelline, as well as the polyphenol chlorogenic acid, are some of the most important bioactive organic compounds of these beverages, displaying high levels in both espresso and common brews and/or increased bioavailability after consumption."	( Drinking for protection? Epidemiological and experimental evidence on the beneficial effects of coffee or major coffee compounds against gastrointestinal and liver carcinogenesis. Barbisan, LF; Chaves, MAG; Cogliati, B; Moreno, FS; Rocha, AB; Romualdo, GR; Vinken, M, 2019)	0.75
" Due to the difficulty of extraction and purification, poor stability, poor solubility, low absolute bioavailability of oral administration, the possibility of allergies caused by injection, and so on, there are difficulties in its medicinal research and development."	( Pharmacological action and potential targets of chlorogenic acid. Miao, M; Xiang, L, 2020)	0.81
" It is currently unknown whether these protective effects are related to caffeine (CAF), or to its combination with other common and/or highly bioavailable coffee compounds, such as trigonelline (TRI) and chlorogenic acid (CGA)."	( The combination of coffee compounds attenuates early fibrosis-associated hepatocarcinogenesis in mice: involvement of miRNA profile modulation. Barbisan, LF; Cogliati, B; da Silva, TC; Evangelista, AF; Moreno, FS; Prata, GB; Reis, RM; Romualdo, GR; Vinken, M, 2020)	0.75
" However, the bioavailability of curcumin is a major barrier to its biological efficacy."	( Chlorogenic Acid Potentiates the Anti-Inflammatory Activity of Curcumin in LPS-Stimulated THP-1 Cells. Bisht, A; Dickens, M; Mutukumira, AN; Rutherfurd-Markwick, K; Singh, H; Thota, R, 2020)	2
" However, little research has been conducted concerning the bioavailability of polyphenols, especially in the colon."	( Simulated Gastrointestinal Biotransformation of Chlorogenic Acid, Flavonoids, Flavonolignans and Triterpenoid Saponins in Cecropia obtusifolia Leaf Extract. Breynaert, A; Caballero-George, C; Foubert, K; Hermans, N; Peeters, L; Pieters, L; Rivera-Mondragón, A; Van, AA, 2021)	0.88
" These effects are dependent on the bioavailability of chlorogenic acid, which is determined by the pharmacokinetic properties: absorption, distribution, metabolism and excretion (ADME)."	( Demonstrating the involvement of an active efflux mechanism in the intestinal absorption of chlorogenic acid and quinic acid using a Caco-2 bidirectional permeability assay. Hermans, N; Jörissen, J; Lebeer, S; Mortelé, O; Spacova, I; van Nuijs, ALN, 2021)	1.09
" The results showed that caffeine and ferulic acid, as well as green Robusta coffee, demonstrated the greatest inhibition of MAO-A activity, which may increase the bioavailability of serotonin."	( Evaluation of the inhibition of monoamine oxidase A by bioactive coffee compounds protecting serotonin degradation. Budryn, G; Gałązka-Czarnecka, I; Grzelczyk, J; Oracz, J; Peña-García, J; Pérez-Sánchez, H; Szwajgier, D, 2021)	0.62
" Self-microemulsifying drug delivery systems (SMEDDS) have attracted increasing attention to improving oral bioavailability by taking advantage of the intestinal lymphatic transport pathway."	( Oral SMEDDS promotes lymphatic transport and mesenteric lymph nodes target of chlorogenic acid for effective T-cell antitumor immunity. Chen, X; Gao, L; Gao, Y; Ji, M; Jin, J; Li, L; Li, R; Li, Y; Lian, C; Liao, H; Liu, Y; Sun, T; Wang, B; Wang, H; Wang, Z; Xu, X; Xu, Y; Yang, Y; Ye, J, 2021)	0.85
" The results confirm that changes in gut microbiota related to obesity are associated with differences in microbiotic biotransformation of xenobiotics and thus possibly influencing the activity, bioavailability and toxicity of orally administered xenobiotics and drugs."	( Obesity influences the microbiotic biotransformation of chlorogenic acid. Dirinck, E; Hermans, N; Jorens, PG; Lammens, C; Malhotra-Kumar, S; Mortelé, O; van Nuijs, ALN; Xavier, BB, 2022)	0.97
" Further studies should focus on active concentrations and bioavailability of polyphenols, confirming optimal intake and hypoallergenic of polyphenols based on clinical trials."	( A review on polyphenols and their potential application to reduce food allergenicity. Cheng, J; Fu, G; Guo, M; Pi, X; Sun, Y, 2023)	0.91
" The in vivo intestinal absorption rate of chlorogenic acid (CA), the active component of the EEGS, both in a single form and in the EEGS were monitored by the single-pass intestinal perfusion (SPIP) method in rats."	( Synergistic effects of trans-p-coumaric acid isolated from the ethanol extract of Gynura procumbens in promoting intestinal absorption of chlorogenic acid and reversing alcoholic fatty liver disease. He, YM; Huang, XL; Li, YS; Mu, YM; Tang, HB; Wang, C, 2022)	1.19
" Among the 12 main components identified, five main compounds were well absorbed with Papp in the order of benzoic acid > chlorogenic acid > astragaloside > hyperoside > rutin."	( The transported active mulberry leaf phenolics inhibited adipogenesis through PPAR-γ and Leptin signaling pathway. Li, E; Li, Q; Liao, S; Liu, F; Liu, T; Pang, D; Zou, Y, 2022)	0.93
" Currently, the main drug treatment is antibiotic therapy; however, systemic antibiotic therapy still has various drawbacks such as bacterial resistance, low bioavailability and burst release."	( Sustained release of chlorogenic acid-loaded nanomicelles alleviates bone loss in mouse periodontitis. Fang, X; Hu, JF; Hu, QY; Li, H; Sun, ZJ; Xu, J; Xu, Z; Zhang, L, 2022)	1.04
" Despite its low oral bioavailability (about 33%), CGA has drawn considerable attention due to its wide range of biological activities and numerous molecular targets."	( Chlorogenic Acid: A Dietary Phenolic Acid with Promising Pharmacotherapeutic Potential. Pandey, AK; Singh, AK; Singla, RK, 2023)	2.35
"In this study, a combined in vitro digestion/Caco-2 model was performed with the aim to determine the phenolic compounds bioavailability of two yarrow extracts."	( Bioavailability Assessment of Yarrow Phenolic Compounds Using an In Vitro Digestion/Caco-2 Cell Model: Anti-Inflammatory Activity of Basolateral Fraction. Jaime, L; Santoyo, S; Siles-Sánchez, MLN; Villalva, M, 2022)	0.72
" These findings provide mechanistic insights into the therapeutic use of herbal ingredients with poor bioavailability via their interaction with the gut microbiota."	( Limosilactobacillus reuteri and caffeoylquinic acid synergistically promote adipose browning and ameliorate obesity-associated disorders. Guo, X; Li, C; Liang, X; Lin, S; Liu, Y; Wang, J; Wang, K; Wang, Y; Xie, C; Xu, H; Xu, J; Yu, M; Zhong, X, 2022)	0.72
" However, due to the low bioavailability of CGA, its application dose is usually high in vivo."	( A Flower-like Brain Targeted Selenium Nanocluster Lowers the Chlorogenic Acid Dose for Ameliorating Cognitive Impairment in APP/PS1 Mice. Cui, Y; Li, C; Li, Z; Liang, H; Wang, N; Wang, Y; Yang, L; Zheng, G, 2023)	1.15
" For in-vitro experiment, the modified Franz diffusion cell method was used to determine the transdermal absorption rate and 24h cumulative transdermal absorption amount of the active ingredients of crossbow-medicine liquid."	( Effect of microneedle roller on promoting transdermal absorption of crossbow-medicine liquid via transdermal administration of Traditional Chinese Medicine and the safety of crossbow-medicine needle therapy: An experimental study. Cui, J; Luo, H; Zan, F, 2023)	0.91
" The 24h cumulative transdermal absorption amount and transdermal absorption rate of each ingredient in microneedle-roller group were significantly higher than those in crossbow-medicine liquid application group (all P < 0."	( Effect of microneedle roller on promoting transdermal absorption of crossbow-medicine liquid via transdermal administration of Traditional Chinese Medicine and the safety of crossbow-medicine needle therapy: An experimental study. Cui, J; Luo, H; Zan, F, 2023)	0.91

Excerpt	Relevance	Reference
" Dose-response curves did show reduction of CSC- and BaP-induced mutagenicity by ellagic acid, riboflavin and chlorophyllin."	( Antimutagenic activity of some naturally occurring compounds towards cigarette-smoke condensate and benzo[a]pyrene in the Salmonella/microsome assay. Terwel, L; van der Hoeven, JC, 1985)	0.27
" 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
" In the present study, the dose-response for CGA in HHQ-free coffee on BP were investigated in mildly hypertensive men and women."	( Hydroxyhydroquinone-free coffee: a double-blind, randomized controlled dose-response study of blood pressure. Chikama, A; Katsuragi, Y; Mori, K; Shioya, Y; Tokimitsu, I; Watanabe, T; Yamaguchi, T, 2008)	0.35
" As a result, a significant correlation between BP change and the three dose-response patterns was observed (p<0."	( Hydroxyhydroquinone-free coffee: a double-blind, randomized controlled dose-response study of blood pressure. Chikama, A; Katsuragi, Y; Mori, K; Shioya, Y; Tokimitsu, I; Watanabe, T; Yamaguchi, T, 2008)	0.35
" Most studies confirm a protective effect against type 2 diabetes, with some dose-response in function of the degree of daily coffee consumption."	( [Does coffee protect against type 2 diabetes?]. Legrand, D; Scheen, AJ, 2007)	0.34
" A low dosage of ferulic acid in rodent diets stimulates insulin production and alleviates symptoms caused by diabetes (M."	( Biochemical properties of two cinnamoyl esterases purified from a Lactobacillus johnsonii strain isolated from stool samples of diabetes-resistant rats. Gonzalez, CF; Lai, KK; Lorca, GL, 2009)	0.35
" Mice nasally immunized with OVA plus CT and an optimal dosage of APE showed significantly reduced levels of inflammatory responses as well as total and OVA-specific IgE antibodies when compared with mice given without APE."	( Co-administration of cholera toxin and apple polyphenol extract as a novel and safe mucosal adjuvant strategy. Fujihashi, K; Hagiwara, Y; Inaba, N; Kanno, H; Kobayashi, R; Noda, M; Sato, S; Takahashi, K; Yoshino, N, 2009)	0.35
" Furthermore, chlorogenic acid significantly reduced the adhesion of human monocyte cells (U937) to IL-1beta-treated HUVECs in a dose-response manner."	( Chlorogenic acid attenuates adhesion molecules upregulation in IL-1beta-treated endothelial cells. Chang, T; Chang, WC; Chen, CH; Lee, MF; Yu, YM, 2010)	2.16
" The behavioral activity of extracts dosed intraperitoneally in the range 100-400 mg/kg was examined in adult male Wistar rats, in the elevated plus maze, spontaneous locomotor activity, and grip strength tests, mainly predictive of anxiolytic, sedative and myorelaxant actions, respectively."	( Behavioural characterization of four endemic Stachys taxa. Cook, JM; Divljaković, J; Grayer, RJ; Kukić, JM; Marin, PD; Milinković, MM; Petrović, SD; Savić, MM; Van Linn, M, 2010)	0.36
" Together the present study clearly reflects that combined dosage of tetrahydrocurcumin and chlorogenic acid augments enzymic antioxidants with a concomitant decrease in lipid peroxidation and protects against streptozotocin-nicotinamide-induced type 2 diabetes in experimental rats."	( Comparative and combined effect of chlorogenic acid and tetrahydrocurcumin on antioxidant disparities in chemical induced experimental diabetes. Karthikesan, K; Menon, VP; Pari, L, 2010)	0.86
" To assess absorption in the small intestine, we performed a dose-response study with a randomized, double-blinded, crossover design with ileostomist subjects."	( Dose-dependent absorption of chlorogenic acids in the small intestine assessed by coffee consumption in ileostomists. Barron, D; Dionisi, F; Erk, T; Marmet, C; Melcher, R; Renouf, M; Richling, E; Steiling, H; Williamson, G, 2012)	0.67
" Results from both in vitro, in situ as well as in vivo studies consistently indicated that Chito-oligosaccharide (COS) at dosage of 25 mg/kg could enhance intestinal permeabilities significantly as well as the in vivo bioavailabilities of both FTA and CHA than CMCs in Flos Lonicerae-Fructus Forsythiae herb couple preparations, and was safe for gastrointestine from morphological observation."	( Improvement of intestinal absorption of forsythoside A and chlorogenic acid by different carboxymethyl chitosan and chito-oligosaccharide, application to Flos Lonicerae-Fructus Forsythiae herb couple preparations. Cai, B; Di, L; Shan, J; Wang, H; Yin, A; Zhou, W; Zhu, X, 2013)	0.63
"We performed a dose-response study measuring plasma bioavailability of phenolics after drinking three increasing, but still nutritionally relevant doses of instant pure soluble coffee."	( Dose-response plasma appearance of coffee chlorogenic and phenolic acids in adults. Barron, D; Beaumont, M; Dionisi, F; Giuffrida, F; Lepage, M; Marmet, C; Renouf, M; Williamson, G, 2014)	0.4
"This study confirmed previous findings about coffee bioavailability but also showed that coffee phenolics appear in a positive dose-response manner in plasma when drank at nutritionally relevant doses."	( Dose-response plasma appearance of coffee chlorogenic and phenolic acids in adults. Barron, D; Beaumont, M; Dionisi, F; Giuffrida, F; Lepage, M; Marmet, C; Renouf, M; Williamson, G, 2014)	0.4
" Dose-response curves for FAO were constructed and the highest non-effective dose (typically 1-10 nM) was used with either leucine (0."	( Synergistic effects of polyphenols and methylxanthines with Leucine on AMPK/Sirtuin-mediated metabolism in muscle cells and adipocytes. Bruckbauer, A; Zemel, MB, 2014)	0.4
" The recommended application dosage is 200 mg kg(-1) and further studies are needed to clarify the action model of CGA efficiency."	( Effects of dietary chlorogenic acid on growth performance, antioxidant capacity of white shrimp Litopenaeus vannamei under normal condition and combined stress of low-salinity and nitrite. Duan, YF; Huang, Z; Li, J; Li, Z; Lin, HZ; Niu, J; Wang, J; Wang, Y, 2015)	0.75
" After investigation of their dose-response behaviors and structure-activity relationships, chlorogenic acids and flavonoid glycosides were found to be DNA-binders via both minor groove-binding and intercalation modes."	( An analysis method for simultaneous screening of deoxyribonucleic acid-binding active compounds and investigating their mechanisms by ultra-fast liquid chromatography tandem mass spectrometry coupled with fluorescence detection technology. Chen, S; Lin, Z; Ren, B; Tong, L; Wang, H; Zhang, C, 2015)	0.64
" In order to investigate the protective effects of CA on alcohol-induced apoptosis in rat pheochromocytoma PC12 cells, in the present study, cell viability and the optimal dosage of CA were first quantified by MTT assay."	( Beneficial effects of chlorogenic acid on alcohol-induced damage in PC12 cells. Fang, SQ; Lu, XM; Shu, YH; Wang, YT; Wei, JX; Xiao, L, 2016)	0.75
"Decoction of single medicinal herb is a reference for the standardization of different dosage form of Chinese medicine and it provides a new direction for solving the problems existing in the quality of Chinese medicinal granules such no uniform dosage forms and no clear quality standard."	( [Quality evaluation of decoction of single medicinal herb--a case of Lonicerae Japinicae Flos]. Chen, SL; Dai, YT; Dong, Q; Fan, ZQ; Li, Q; Takehisa, T; Tong, JY; Wang, DD, 2017)	0.46
"To investigate the optimal dosage ratio of chlorogenic acid and gardenia glycosides in\ treating the rates with fatty liver disease induced by high-fat feed."	( Optimization of dosage ratio of chlorogenic acid and gardenia glycosides in the treatment of rats with fatty liver disease induced by\ high-fat feed. Chen, S; Li, H; Liang, H; Tang, J; Wu, C; Yang, J, 2016)	0.98
" Multiple\ regression analysis was conducted to test the optimal dosage ratio of chlorogenic acid and gardenia\ glycosides."	( Optimization of dosage ratio of chlorogenic acid and gardenia glycosides in the treatment of rats with fatty liver disease induced by\ high-fat feed. Chen, S; Li, H; Liang, H; Tang, J; Wu, C; Yang, J, 2016)	0.94
" Combination of 90 mg chlorogenic\ acid and 90 mg Gardenia glycosides was the optimal dosage ratio of chlorogenic acid and gardenia\ glycosides in the treatment of rats with fatty liver induced by high-fat diet."	( Optimization of dosage ratio of chlorogenic acid and gardenia glycosides in the treatment of rats with fatty liver disease induced by\ high-fat feed. Chen, S; Li, H; Liang, H; Tang, J; Wu, C; Yang, J, 2016)	0.93
"Standard decoction of traditional Chinese medicine (TCM) is prepared by standardized process, and can be used as references to evaluate the quality of dosage forms such as decoction and dispensing granules."	( [Research and application of quality standard for standard decoction of Chrysanthemi Flos]. Hao, YD; Li, DH; Wang, JN, 2018)	0.48
" Additionally, the thermal dosage in the treatment of cancer cells could also probably harm the healthy cells."	( Thermal cycling-hyperthermia in combination with polyphenols, epigallocatechin gallate and chlorogenic acid, exerts synergistic anticancer effect against human pancreatic cancer PANC-1 cells. Chao, CY; Chen, WT; Hsieh, CH; Kuo, YY; Lu, CH, 2019)	0.73
" 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
" In order to have a better understanding of the biological properties of chlorogenic acid and to optimize formulation and dosing of chlorogenic acid-containing food supplements, information on the absorption of chlorogenic acid and its microbial biotransformation products is of essence."	( Demonstrating the involvement of an active efflux mechanism in the intestinal absorption of chlorogenic acid and quinic acid using a Caco-2 bidirectional permeability assay. Hermans, N; Jörissen, J; Lebeer, S; Mortelé, O; Spacova, I; van Nuijs, ALN, 2021)	1.07
" These findings could aid in the development of optimal formulation and dosing strategies of chlorogenic acid in food supplements in order to obtain beneficial health effects."	( Demonstrating the involvement of an active efflux mechanism in the intestinal absorption of chlorogenic acid and quinic acid using a Caco-2 bidirectional permeability assay. Hermans, N; Jörissen, J; Lebeer, S; Mortelé, O; Spacova, I; van Nuijs, ALN, 2021)	1.06
" Combining the previous analysis of qualitative and quantitative preparation quality markers of Yulian Tang with the above result of dose-response relationship, we finally identified 15 preparation quality markers of Yulian Tang with anti-inflammatory activity, namely berberine, coptisine, palmatine, magnoflorine, epiberberine, limonin, columbamine, jatrorrhizine, neochlorogenic acid, chlorogenic acid, groenlandicine, evodiamine, rutaecarpine, dehydrocostus lactone and costunolide."	( [Research of preparation quality markers of Yulian Tang with anti-inflammatory activity]. DU, MB; Gu, WW; Li, T; Li, X; Liu, SZ; Mu, J; Ran, QS; Shen, S; Xu, J, 2022)	0.89
"(5) Optimal dosing and timing are approximately two to four cups (approximately 473-946 ml or 16-32 oz."	( International society of sports nutrition position stand: coffee and sports performance. Anderson, DE; Antonio, J; Campbell, BI; Campbell, SC; Escalante, G; Kalman, DS; Kerksick, CM; Kreider, RB; Lowery, LM; Nelson, MT; Scanlon, KF; Stack, A; VanDusseldorp, TA; Ziegenfuss, TN, 2023)	0.91

Role	Description
plant metabolite	Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
food component	A physiological role played by any substance that is distributed in foodstuffs. It includes materials derived from plants or animals, such as vitamins or minerals, as well as environmental contaminants.
[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
tannin	Any of a group of astringent polyphenolic vegetable principles or compounds, chiefly complex glucosides of catechol and pyrogallol.
cinnamate ester
[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
Flavonoid Biosynthesis	11	50
Stilbenoid, Diarylheptanoid, and Gingerol Biosynthesis	4	17
chlorogenic acid degradation	0	5

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Chain A, JmjC domain-containing histone demethylation protein 3A	Homo sapiens (human)	Potency	17.7828	0.6310	35.7641	100.0000	AID504339
GLS protein	Homo sapiens (human)	Potency	35.4813	0.3548	7.9355	39.8107	AID624170
apical membrane antigen 1, AMA1	Plasmodium falciparum 3D7	Potency	39.8107	0.7079	12.1943	39.8107	AID720542
euchromatic histone-lysine N-methyltransferase 2	Homo sapiens (human)	Potency	12.5893	0.0355	20.9770	89.1251	AID504332
thyroid stimulating hormone receptor	Homo sapiens (human)	Potency	55.3704	0.0016	28.0151	77.1139	AID1259385
Histone H2A.x	Cricetulus griseus (Chinese hamster)	Potency	25.2586	0.0391	47.5451	146.8240	AID1224845; AID1224896
urokinase-type plasminogen activator precursor	Mus musculus (house mouse)	Potency	1.1220	0.1585	5.2879	12.5893	AID540303
plasminogen precursor	Mus musculus (house mouse)	Potency	1.1220	0.1585	5.2879	12.5893	AID540303
urokinase plasminogen activator surface receptor precursor	Mus musculus (house mouse)	Potency	1.1220	0.1585	5.2879	12.5893	AID540303
geminin	Homo sapiens (human)	Potency	3.2643	0.0046	11.3741	33.4983	AID624297
Rap guanine nucleotide exchange factor 3	Homo sapiens (human)	Potency	31.6228	6.3096	60.2008	112.2020	AID720709
Rap guanine nucleotide exchange factor 4	Homo sapiens (human)	Potency	39.8107	3.9811	46.7448	112.2020	AID720708
[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)
1,3-beta-D-glucan synthase catalytic subunit	Candida albicans	IC50 (µMol)	90.0000	0.0002	0.0002	0.0002	AID515789
Histone deacetylase 3	Homo sapiens (human)	IC50 (µMol)	258.3333	0.0004	0.6196	10.0000	AID1293874; AID1293875; AID447579
Histone deacetylase 3	Homo sapiens (human)	Ki	0.1350	0.0002	0.4237	8.1900	AID447579
Aldo-keto reductase family 1 member B10	Homo sapiens (human)	IC50 (µMol)	7.9000	0.0010	1.9445	9.6000	AID641086
Amyloid-beta precursor protein	Homo sapiens (human)	IC50 (µMol)	92.9000	0.0005	3.8895	10.0000	AID688479
Aldo-keto reductase family 1 member B1	Rattus norvegicus (Norway rat)	IC50 (µMol)	0.9500	0.0004	1.8773	10.0000	AID654333
Replicase polyprotein 1ab	Severe acute respiratory syndrome-related coronavirus	IC50 (µMol)	39.4800	0.0040	2.9266	9.9600	AID1805801
Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	IC50 (µMol)	39.4800	0.0002	2.4585	9.9600	AID1805801
Aldo-keto reductase family 1 member B1	Homo sapiens (human)	IC50 (µMol)	1.0500	0.0010	1.1913	10.0000	AID639825; AID641085
Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)	IC50 (µMol)	77.9000	0.7000	4.5804	9.4500	AID1374940
Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)	IC50 (µMol)	5.6000	0.0005	3.4984	9.7600	AID1374929; AID1755200
Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)	Ki	4,107.5500	0.1900	4.8327	9.6000	AID1374930; AID1802327
Histone deacetylase 4	Homo sapiens (human)	IC50 (µMol)	258.3333	0.0006	1.0526	10.0000	AID1293874; AID1293875; AID447579
Histone deacetylase 4	Homo sapiens (human)	Ki	0.1350	0.0002	1.6255	9.1242	AID447579
Histone deacetylase 1	Homo sapiens (human)	IC50 (µMol)	258.3333	0.0001	0.5543	9.9000	AID1293874; AID1293875; AID447579
Histone deacetylase 1	Homo sapiens (human)	Ki	0.1350	0.0000	0.4988	8.1900	AID447579
Integrase	Human immunodeficiency virus 1	IC50 (µMol)	59.4500	0.0005	1.5443	10.0000	AID91425; AID91426; AID93700; AID93702; AID93705; AID93707
Histone deacetylase 7	Homo sapiens (human)	IC50 (µMol)	258.3333	0.0007	1.0260	9.9000	AID1293874; AID1293875; AID447579
Histone deacetylase 7	Homo sapiens (human)	Ki	0.1350	0.0002	2.0005	9.5000	AID447579
Histone deacetylase 2	Homo sapiens (human)	IC50 (µMol)	258.3333	0.0001	0.7221	9.9700	AID1293874; AID1293875; AID447579
Histone deacetylase 2	Homo sapiens (human)	Ki	0.1350	0.0000	0.4709	8.1900	AID447579
Polyamine deacetylase HDAC10	Homo sapiens (human)	IC50 (µMol)	258.3333	0.0005	0.7245	9.9000	AID1293874; AID1293875; AID447579
Polyamine deacetylase HDAC10	Homo sapiens (human)	Ki	0.1350	0.0000	0.7687	8.1900	AID447579
Histone deacetylase 11	Homo sapiens (human)	IC50 (µMol)	258.3333	0.0003	0.9298	9.9000	AID1293874; AID1293875; AID447579
Histone deacetylase 11	Homo sapiens (human)	Ki	0.1350	0.0001	1.2147	8.1900	AID447579
Histone deacetylase 8	Homo sapiens (human)	IC50 (µMol)	258.3333	0.0007	0.9947	9.9000	AID1293874; AID1293875; AID447579
Histone deacetylase 8	Homo sapiens (human)	Ki	0.1350	0.0002	0.7525	8.1900	AID447579
Histone deacetylase 6	Homo sapiens (human)	IC50 (µMol)	258.3333	0.0000	0.5376	9.9000	AID1293874; AID1293875; AID447579
Histone deacetylase 6	Homo sapiens (human)	Ki	0.1350	0.0001	0.4156	8.1900	AID447579
Histone deacetylase 9	Homo sapiens (human)	IC50 (µMol)	258.3333	0.0005	0.9413	9.9000	AID1293874; AID1293875; AID447579
Histone deacetylase 9	Homo sapiens (human)	Ki	0.1350	0.0002	1.8520	9.0000	AID447579
Histone deacetylase 5	Homo sapiens (human)	IC50 (µMol)	258.3333	0.0007	0.9610	10.0000	AID1293874; AID1293875; AID447579
Histone deacetylase 5	Homo sapiens (human)	Ki	0.1350	0.0002	1.2993	9.5000	AID447579
large T antigen	Betapolyomavirus macacae	IC50 (µMol)	14.6700	0.1600	24.9724	100.0000	AID1903
[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)
Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)	Kd	1,500.0000	6.0800	6.0800	6.0800	AID1802328
[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	1.2600	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
negative regulation of myotube differentiation	Histone deacetylase 3	Homo sapiens (human)
negative regulation of transcription by RNA polymerase II	Histone deacetylase 3	Homo sapiens (human)
establishment of mitotic spindle orientation	Histone deacetylase 3	Homo sapiens (human)
in utero embryonic development	Histone deacetylase 3	Homo sapiens (human)
positive regulation of protein phosphorylation	Histone deacetylase 3	Homo sapiens (human)
chromatin organization	Histone deacetylase 3	Homo sapiens (human)
transcription by RNA polymerase II	Histone deacetylase 3	Homo sapiens (human)
protein deacetylation	Histone deacetylase 3	Homo sapiens (human)
regulation of mitotic cell cycle	Histone deacetylase 3	Homo sapiens (human)
positive regulation of protein ubiquitination	Histone deacetylase 3	Homo sapiens (human)
regulation of protein stability	Histone deacetylase 3	Homo sapiens (human)
positive regulation of TOR signaling	Histone deacetylase 3	Homo sapiens (human)
circadian regulation of gene expression	Histone deacetylase 3	Homo sapiens (human)
regulation of multicellular organism growth	Histone deacetylase 3	Homo sapiens (human)
positive regulation of protein import into nucleus	Histone deacetylase 3	Homo sapiens (human)
regulation of circadian rhythm	Histone deacetylase 3	Homo sapiens (human)
negative regulation of apoptotic process	Histone deacetylase 3	Homo sapiens (human)
negative regulation of DNA-templated transcription	Histone deacetylase 3	Homo sapiens (human)
positive regulation of transcription by RNA polymerase II	Histone deacetylase 3	Homo sapiens (human)
negative regulation of JNK cascade	Histone deacetylase 3	Homo sapiens (human)
spindle assembly	Histone deacetylase 3	Homo sapiens (human)
establishment of skin barrier	Histone deacetylase 3	Homo sapiens (human)
cellular response to fluid shear stress	Histone deacetylase 3	Homo sapiens (human)
positive regulation of cold-induced thermogenesis	Histone deacetylase 3	Homo sapiens (human)
DNA repair-dependent chromatin remodeling	Histone deacetylase 3	Homo sapiens (human)
cornified envelope assembly	Histone deacetylase 3	Homo sapiens (human)
negative regulation of cardiac muscle cell differentiation	Histone deacetylase 3	Homo sapiens (human)
epigenetic regulation of gene expression	Histone deacetylase 3	Homo sapiens (human)
retinoid metabolic process	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
farnesol catabolic process	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
retinol metabolic process	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
daunorubicin metabolic process	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
doxorubicin metabolic process	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
cellular detoxification of aldehyde	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
angiogenesis	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
adaptive immune response	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
signal transduction	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathway	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
associative learning	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
Rap protein signal transduction	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
regulation of actin cytoskeleton organization	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
negative regulation of syncytium formation by plasma membrane fusion	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
intracellular signal transduction	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
positive regulation of GTPase activity	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
regulation of angiogenesis	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
positive regulation of angiogenesis	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
positive regulation of protein export from nucleus	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
positive regulation of stress fiber assembly	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
regulation of phosphatidylinositol 3-kinase/protein kinase B signal transduction	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
positive regulation of syncytium formation by plasma membrane fusion	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
establishment of endothelial barrier	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
cellular response to cAMP	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
Ras protein signal transduction	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
regulation of insulin secretion	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
regulation of gene expression	Amyloid-beta precursor protein	Homo sapiens (human)
cognition	Amyloid-beta precursor protein	Homo sapiens (human)
G2/M transition of mitotic cell cycle	Amyloid-beta precursor protein	Homo sapiens (human)
microglial cell activation	Amyloid-beta precursor protein	Homo sapiens (human)
positive regulation of protein phosphorylation	Amyloid-beta precursor protein	Homo sapiens (human)
suckling behavior	Amyloid-beta precursor protein	Homo sapiens (human)
astrocyte activation involved in immune response	Amyloid-beta precursor protein	Homo sapiens (human)
regulation of translation	Amyloid-beta precursor protein	Homo sapiens (human)
protein phosphorylation	Amyloid-beta precursor protein	Homo sapiens (human)
intracellular copper ion homeostasis	Amyloid-beta precursor protein	Homo sapiens (human)
endocytosis	Amyloid-beta precursor protein	Homo sapiens (human)
response to oxidative stress	Amyloid-beta precursor protein	Homo sapiens (human)
cell adhesion	Amyloid-beta precursor protein	Homo sapiens (human)
regulation of epidermal growth factor-activated receptor activity	Amyloid-beta precursor protein	Homo sapiens (human)
Notch signaling pathway	Amyloid-beta precursor protein	Homo sapiens (human)
axonogenesis	Amyloid-beta precursor protein	Homo sapiens (human)
learning or memory	Amyloid-beta precursor protein	Homo sapiens (human)
learning	Amyloid-beta precursor protein	Homo sapiens (human)
mating behavior	Amyloid-beta precursor protein	Homo sapiens (human)
locomotory behavior	Amyloid-beta precursor protein	Homo sapiens (human)
axo-dendritic transport	Amyloid-beta precursor protein	Homo sapiens (human)
cholesterol metabolic process	Amyloid-beta precursor protein	Homo sapiens (human)
negative regulation of cell population proliferation	Amyloid-beta precursor protein	Homo sapiens (human)
adult locomotory behavior	Amyloid-beta precursor protein	Homo sapiens (human)
visual learning	Amyloid-beta precursor protein	Homo sapiens (human)
regulation of gene expression	Amyloid-beta precursor protein	Homo sapiens (human)
positive regulation of gene expression	Amyloid-beta precursor protein	Homo sapiens (human)
negative regulation of gene expression	Amyloid-beta precursor protein	Homo sapiens (human)
positive regulation of peptidyl-threonine phosphorylation	Amyloid-beta precursor protein	Homo sapiens (human)
positive regulation of G2/M transition of mitotic cell cycle	Amyloid-beta precursor protein	Homo sapiens (human)
microglia development	Amyloid-beta precursor protein	Homo sapiens (human)
axon midline choice point recognition	Amyloid-beta precursor protein	Homo sapiens (human)
neuron remodeling	Amyloid-beta precursor protein	Homo sapiens (human)
dendrite development	Amyloid-beta precursor protein	Homo sapiens (human)
regulation of Wnt signaling pathway	Amyloid-beta precursor protein	Homo sapiens (human)
extracellular matrix organization	Amyloid-beta precursor protein	Homo sapiens (human)
forebrain development	Amyloid-beta precursor protein	Homo sapiens (human)
neuron projection development	Amyloid-beta precursor protein	Homo sapiens (human)
positive regulation of chemokine production	Amyloid-beta precursor protein	Homo sapiens (human)
positive regulation of interleukin-1 beta production	Amyloid-beta precursor protein	Homo sapiens (human)
positive regulation of interleukin-6 production	Amyloid-beta precursor protein	Homo sapiens (human)
positive regulation of tumor necrosis factor production	Amyloid-beta precursor protein	Homo sapiens (human)
positive regulation of peptidyl-serine phosphorylation	Amyloid-beta precursor protein	Homo sapiens (human)
ionotropic glutamate receptor signaling pathway	Amyloid-beta precursor protein	Homo sapiens (human)
regulation of multicellular organism growth	Amyloid-beta precursor protein	Homo sapiens (human)
negative regulation of neuron differentiation	Amyloid-beta precursor protein	Homo sapiens (human)
positive regulation of glycolytic process	Amyloid-beta precursor protein	Homo sapiens (human)
positive regulation of mitotic cell cycle	Amyloid-beta precursor protein	Homo sapiens (human)
positive regulation of transcription by RNA polymerase II	Amyloid-beta precursor protein	Homo sapiens (human)
positive regulation of JNK cascade	Amyloid-beta precursor protein	Homo sapiens (human)
astrocyte activation	Amyloid-beta precursor protein	Homo sapiens (human)
regulation of long-term neuronal synaptic plasticity	Amyloid-beta precursor protein	Homo sapiens (human)
collateral sprouting in absence of injury	Amyloid-beta precursor protein	Homo sapiens (human)
positive regulation of inflammatory response	Amyloid-beta precursor protein	Homo sapiens (human)
regulation of peptidyl-tyrosine phosphorylation	Amyloid-beta precursor protein	Homo sapiens (human)
regulation of synapse structure or activity	Amyloid-beta precursor protein	Homo sapiens (human)
synapse organization	Amyloid-beta precursor protein	Homo sapiens (human)
positive regulation of calcium-mediated signaling	Amyloid-beta precursor protein	Homo sapiens (human)
neuromuscular process controlling balance	Amyloid-beta precursor protein	Homo sapiens (human)
synaptic assembly at neuromuscular junction	Amyloid-beta precursor protein	Homo sapiens (human)
positive regulation of protein metabolic process	Amyloid-beta precursor protein	Homo sapiens (human)
neuron apoptotic process	Amyloid-beta precursor protein	Homo sapiens (human)
smooth endoplasmic reticulum calcium ion homeostasis	Amyloid-beta precursor protein	Homo sapiens (human)
neuron cellular homeostasis	Amyloid-beta precursor protein	Homo sapiens (human)
positive regulation of ERK1 and ERK2 cascade	Amyloid-beta precursor protein	Homo sapiens (human)
response to interleukin-1	Amyloid-beta precursor protein	Homo sapiens (human)
modulation of excitatory postsynaptic potential	Amyloid-beta precursor protein	Homo sapiens (human)
NMDA selective glutamate receptor signaling pathway	Amyloid-beta precursor protein	Homo sapiens (human)
regulation of spontaneous synaptic transmission	Amyloid-beta precursor protein	Homo sapiens (human)
cytosolic mRNA polyadenylation	Amyloid-beta precursor protein	Homo sapiens (human)
negative regulation of long-term synaptic potentiation	Amyloid-beta precursor protein	Homo sapiens (human)
positive regulation of long-term synaptic potentiation	Amyloid-beta precursor protein	Homo sapiens (human)
positive regulation of non-canonical NF-kappaB signal transduction	Amyloid-beta precursor protein	Homo sapiens (human)
cellular response to amyloid-beta	Amyloid-beta precursor protein	Homo sapiens (human)
regulation of presynapse assembly	Amyloid-beta precursor protein	Homo sapiens (human)
positive regulation of amyloid fibril formation	Amyloid-beta precursor protein	Homo sapiens (human)
amyloid fibril formation	Amyloid-beta precursor protein	Homo sapiens (human)
neuron projection maintenance	Amyloid-beta precursor protein	Homo sapiens (human)
positive regulation of T cell migration	Amyloid-beta precursor protein	Homo sapiens (human)
central nervous system development	Amyloid-beta precursor protein	Homo sapiens (human)
symbiont-mediated perturbation of host ubiquitin-like protein modification	Replicase polyprotein 1ab	Severe acute respiratory syndrome-related coronavirus
retinoid metabolic process	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
epithelial cell maturation	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
renal water homeostasis	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
carbohydrate metabolic process	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
prostaglandin metabolic process	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
C21-steroid hormone biosynthetic process	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
L-ascorbic acid biosynthetic process	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
regulation of urine volume	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
retinol metabolic process	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
negative regulation of apoptotic process	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
daunorubicin metabolic process	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
doxorubicin metabolic process	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
fructose biosynthetic process	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
cellular hyperosmotic salinity response	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
metanephric collecting duct development	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
negative regulation of transcription by RNA polymerase II	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
negative regulation of cell population proliferation	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
insulin receptor signaling pathway	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
negative regulation of tumor necrosis factor-mediated signaling pathway	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
negative regulation of lipid storage	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
B cell differentiation	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
T cell differentiation	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
erythrocyte differentiation	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
peptidyl-tyrosine dephosphorylation	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
insulin receptor recycling	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
negative regulation of epidermal growth factor receptor signaling pathway	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
negative regulation of tyrosine phosphorylation of STAT protein	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
glucose homeostasis	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
negative regulation of macrophage differentiation	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
positive regulation of gluconeogenesis	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
negative regulation of insulin receptor signaling pathway	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
negative regulation of inflammatory response	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
negative regulation of T cell receptor signaling pathway	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
negative regulation of chemotaxis	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
regulation of type II interferon-mediated signaling pathway	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
negative regulation of type II interferon-mediated signaling pathway	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
negative regulation of type I interferon-mediated signaling pathway	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
negative regulation of interleukin-6-mediated signaling pathway	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
negative regulation of ERK1 and ERK2 cascade	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
regulation of hepatocyte growth factor receptor signaling pathway	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
negative regulation of interleukin-2-mediated signaling pathway	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
negative regulation of interleukin-4-mediated signaling pathway	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
negative regulation of macrophage colony-stimulating factor signaling pathway	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
negative regulation of positive thymic T cell selection	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
positive regulation of endoplasmic reticulum stress-induced intrinsic apoptotic signaling pathway	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
positive regulation of PERK-mediated unfolded protein response	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
negative regulation of platelet-derived growth factor receptor-beta signaling pathway	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
negative regulation of receptor signaling pathway via JAK-STAT	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
positive regulation of JUN kinase activity	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
protein dephosphorylation	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
insulin receptor signaling pathway	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
regulation of signal transduction	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
negative regulation of signal transduction	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
actin cytoskeleton organization	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
regulation of endocytosis	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
negative regulation of vascular endothelial growth factor receptor signaling pathway	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
endoplasmic reticulum unfolded protein response	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
regulation of intracellular protein transport	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
cellular response to unfolded protein	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
peptidyl-tyrosine dephosphorylation	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
platelet-derived growth factor receptor-beta signaling pathway	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
IRE1-mediated unfolded protein response	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
insulin receptor recycling	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
negative regulation of MAP kinase activity	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
negative regulation of insulin receptor signaling pathway	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
regulation of type I interferon-mediated signaling pathway	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
growth hormone receptor signaling pathway via JAK-STAT	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
positive regulation of protein tyrosine kinase activity	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
negative regulation of ERK1 and ERK2 cascade	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
regulation of hepatocyte growth factor receptor signaling pathway	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
negative regulation of endoplasmic reticulum stress-induced intrinsic apoptotic signaling pathway	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
positive regulation of IRE1-mediated unfolded protein response	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
negative regulation of PERK-mediated unfolded protein response	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
peptidyl-tyrosine dephosphorylation involved in inactivation of protein kinase activity	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
positive regulation of receptor catabolic process	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
negative regulation of transcription by RNA polymerase II	Histone deacetylase 4	Homo sapiens (human)
negative regulation of transcription by RNA polymerase II	Histone deacetylase 4	Homo sapiens (human)
chromatin remodeling	Histone deacetylase 4	Homo sapiens (human)
protein deacetylation	Histone deacetylase 4	Homo sapiens (human)
inflammatory response	Histone deacetylase 4	Homo sapiens (human)
nervous system development	Histone deacetylase 4	Homo sapiens (human)
positive regulation of cell population proliferation	Histone deacetylase 4	Homo sapiens (human)
negative regulation of myotube differentiation	Histone deacetylase 4	Homo sapiens (human)
negative regulation of transcription by competitive promoter binding	Histone deacetylase 4	Homo sapiens (human)
response to denervation involved in regulation of muscle adaptation	Histone deacetylase 4	Homo sapiens (human)
cardiac muscle hypertrophy in response to stress	Histone deacetylase 4	Homo sapiens (human)
protein sumoylation	Histone deacetylase 4	Homo sapiens (human)
B cell differentiation	Histone deacetylase 4	Homo sapiens (human)
positive regulation of protein sumoylation	Histone deacetylase 4	Homo sapiens (human)
peptidyl-lysine deacetylation	Histone deacetylase 4	Homo sapiens (human)
B cell activation	Histone deacetylase 4	Homo sapiens (human)
regulation of protein binding	Histone deacetylase 4	Homo sapiens (human)
negative regulation of DNA-binding transcription factor activity	Histone deacetylase 4	Homo sapiens (human)
negative regulation of gene expression, epigenetic	Histone deacetylase 4	Homo sapiens (human)
negative regulation of glycolytic process	Histone deacetylase 4	Homo sapiens (human)
positive regulation of DNA-templated transcription	Histone deacetylase 4	Homo sapiens (human)
positive regulation of transcription by RNA polymerase II	Histone deacetylase 4	Homo sapiens (human)
positive regulation of DNA-binding transcription factor activity	Histone deacetylase 4	Homo sapiens (human)
type I interferon-mediated signaling pathway	Histone deacetylase 4	Homo sapiens (human)
response to interleukin-1	Histone deacetylase 4	Homo sapiens (human)
response to oxidative stress	Lactoperoxidase	Bos taurus (cattle)
thiocyanate metabolic process	Lactoperoxidase	Bos taurus (cattle)
antibacterial humoral response	Lactoperoxidase	Bos taurus (cattle)
hydrogen peroxide catabolic process	Lactoperoxidase	Bos taurus (cattle)
cellular oxidant detoxification	Lactoperoxidase	Bos taurus (cattle)
negative regulation of myotube differentiation	Histone deacetylase 1	Homo sapiens (human)
negative regulation of apoptotic process	Histone deacetylase 1	Homo sapiens (human)
positive regulation of signaling receptor activity	Histone deacetylase 1	Homo sapiens (human)
negative regulation of transcription by RNA polymerase II	Histone deacetylase 1	Homo sapiens (human)
chromatin organization	Histone deacetylase 1	Homo sapiens (human)
chromatin remodeling	Histone deacetylase 1	Homo sapiens (human)
DNA methylation-dependent heterochromatin formation	Histone deacetylase 1	Homo sapiens (human)
regulation of transcription by RNA polymerase II	Histone deacetylase 1	Homo sapiens (human)
protein deacetylation	Histone deacetylase 1	Homo sapiens (human)
endoderm development	Histone deacetylase 1	Homo sapiens (human)
positive regulation of cell population proliferation	Histone deacetylase 1	Homo sapiens (human)
epidermal cell differentiation	Histone deacetylase 1	Homo sapiens (human)
positive regulation of gene expression	Histone deacetylase 1	Homo sapiens (human)
negative regulation of gene expression	Histone deacetylase 1	Homo sapiens (human)
hippocampus development	Histone deacetylase 1	Homo sapiens (human)
neuron differentiation	Histone deacetylase 1	Homo sapiens (human)
negative regulation of cell migration	Histone deacetylase 1	Homo sapiens (human)
negative regulation of transforming growth factor beta receptor signaling pathway	Histone deacetylase 1	Homo sapiens (human)
circadian regulation of gene expression	Histone deacetylase 1	Homo sapiens (human)
cellular response to platelet-derived growth factor stimulus	Histone deacetylase 1	Homo sapiens (human)
odontogenesis of dentin-containing tooth	Histone deacetylase 1	Homo sapiens (human)
regulation of cell fate specification	Histone deacetylase 1	Homo sapiens (human)
embryonic digit morphogenesis	Histone deacetylase 1	Homo sapiens (human)
negative regulation of apoptotic process	Histone deacetylase 1	Homo sapiens (human)
negative regulation of canonical NF-kappaB signal transduction	Histone deacetylase 1	Homo sapiens (human)
negative regulation by host of viral transcription	Histone deacetylase 1	Homo sapiens (human)
negative regulation of gene expression, epigenetic	Histone deacetylase 1	Homo sapiens (human)
negative regulation of DNA-templated transcription	Histone deacetylase 1	Homo sapiens (human)
positive regulation of DNA-templated transcription	Histone deacetylase 1	Homo sapiens (human)
positive regulation of transcription by RNA polymerase II	Histone deacetylase 1	Homo sapiens (human)
positive regulation of smooth muscle cell proliferation	Histone deacetylase 1	Homo sapiens (human)
oligodendrocyte differentiation	Histone deacetylase 1	Homo sapiens (human)
positive regulation of oligodendrocyte differentiation	Histone deacetylase 1	Homo sapiens (human)
negative regulation of androgen receptor signaling pathway	Histone deacetylase 1	Homo sapiens (human)
hair follicle placode formation	Histone deacetylase 1	Homo sapiens (human)
eyelid development in camera-type eye	Histone deacetylase 1	Homo sapiens (human)
fungiform papilla formation	Histone deacetylase 1	Homo sapiens (human)
negative regulation of canonical Wnt signaling pathway	Histone deacetylase 1	Homo sapiens (human)
negative regulation of stem cell population maintenance	Histone deacetylase 1	Homo sapiens (human)
positive regulation of stem cell population maintenance	Histone deacetylase 1	Homo sapiens (human)
regulation of stem cell differentiation	Histone deacetylase 1	Homo sapiens (human)
negative regulation of intrinsic apoptotic signaling pathway	Histone deacetylase 1	Homo sapiens (human)
heterochromatin formation	Histone deacetylase 1	Homo sapiens (human)
negative regulation of transcription by RNA polymerase II	Histone deacetylase 7	Homo sapiens (human)
vasculogenesis	Histone deacetylase 7	Homo sapiens (human)
chromatin remodeling	Histone deacetylase 7	Homo sapiens (human)
protein deacetylation	Histone deacetylase 7	Homo sapiens (human)
cell-cell junction assembly	Histone deacetylase 7	Homo sapiens (human)
protein sumoylation	Histone deacetylase 7	Homo sapiens (human)
negative regulation of interleukin-2 production	Histone deacetylase 7	Homo sapiens (human)
negative regulation of osteoblast differentiation	Histone deacetylase 7	Homo sapiens (human)
regulation of mRNA processing	Histone deacetylase 7	Homo sapiens (human)
positive regulation of cell migration involved in sprouting angiogenesis	Histone deacetylase 7	Homo sapiens (human)
negative regulation of non-canonical NF-kappaB signal transduction	Histone deacetylase 7	Homo sapiens (human)
adaptive immune response	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
G protein-coupled receptor signaling pathway	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathway	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
calcium-ion regulated exocytosis	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
regulation of exocytosis	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
insulin secretion	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
positive regulation of insulin secretion	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
regulation of synaptic vesicle cycle	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
Ras protein signal transduction	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
regulation of insulin secretion	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
positive regulation of signaling receptor activity	Histone deacetylase 2	Homo sapiens (human)
negative regulation of transcription by RNA polymerase II	Histone deacetylase 2	Homo sapiens (human)
response to amphetamine	Histone deacetylase 2	Homo sapiens (human)
cardiac muscle hypertrophy	Histone deacetylase 2	Homo sapiens (human)
chromatin remodeling	Histone deacetylase 2	Homo sapiens (human)
positive regulation of cell population proliferation	Histone deacetylase 2	Homo sapiens (human)
response to xenobiotic stimulus	Histone deacetylase 2	Homo sapiens (human)
epidermal cell differentiation	Histone deacetylase 2	Homo sapiens (human)
positive regulation of epithelial to mesenchymal transition	Histone deacetylase 2	Homo sapiens (human)
negative regulation of transcription by competitive promoter binding	Histone deacetylase 2	Homo sapiens (human)
negative regulation of neuron projection development	Histone deacetylase 2	Homo sapiens (human)
dendrite development	Histone deacetylase 2	Homo sapiens (human)
negative regulation of cell migration	Histone deacetylase 2	Homo sapiens (human)
negative regulation of transforming growth factor beta receptor signaling pathway	Histone deacetylase 2	Homo sapiens (human)
response to caffeine	Histone deacetylase 2	Homo sapiens (human)
heterochromatin formation	Histone deacetylase 2	Homo sapiens (human)
response to lipopolysaccharide	Histone deacetylase 2	Homo sapiens (human)
positive regulation of interleukin-1 production	Histone deacetylase 2	Homo sapiens (human)
positive regulation of tumor necrosis factor production	Histone deacetylase 2	Homo sapiens (human)
circadian regulation of gene expression	Histone deacetylase 2	Homo sapiens (human)
positive regulation of collagen biosynthetic process	Histone deacetylase 2	Homo sapiens (human)
cellular response to heat	Histone deacetylase 2	Homo sapiens (human)
response to nicotine	Histone deacetylase 2	Homo sapiens (human)
protein modification process	Histone deacetylase 2	Homo sapiens (human)
response to cocaine	Histone deacetylase 2	Homo sapiens (human)
odontogenesis of dentin-containing tooth	Histone deacetylase 2	Homo sapiens (human)
positive regulation of tyrosine phosphorylation of STAT protein	Histone deacetylase 2	Homo sapiens (human)
regulation of cell fate specification	Histone deacetylase 2	Homo sapiens (human)
embryonic digit morphogenesis	Histone deacetylase 2	Homo sapiens (human)
negative regulation of apoptotic process	Histone deacetylase 2	Homo sapiens (human)
negative regulation of DNA-binding transcription factor activity	Histone deacetylase 2	Homo sapiens (human)
negative regulation of MHC class II biosynthetic process	Histone deacetylase 2	Homo sapiens (human)
positive regulation of proteolysis	Histone deacetylase 2	Homo sapiens (human)
negative regulation of DNA-templated transcription	Histone deacetylase 2	Homo sapiens (human)
positive regulation of DNA-templated transcription	Histone deacetylase 2	Homo sapiens (human)
positive regulation of transcription by RNA polymerase II	Histone deacetylase 2	Homo sapiens (human)
behavioral response to ethanol	Histone deacetylase 2	Homo sapiens (human)
positive regulation of oligodendrocyte differentiation	Histone deacetylase 2	Homo sapiens (human)
response to hyperoxia	Histone deacetylase 2	Homo sapiens (human)
hair follicle placode formation	Histone deacetylase 2	Homo sapiens (human)
negative regulation of dendritic spine development	Histone deacetylase 2	Homo sapiens (human)
eyelid development in camera-type eye	Histone deacetylase 2	Homo sapiens (human)
fungiform papilla formation	Histone deacetylase 2	Homo sapiens (human)
cellular response to hydrogen peroxide	Histone deacetylase 2	Homo sapiens (human)
cellular response to retinoic acid	Histone deacetylase 2	Homo sapiens (human)
cellular response to transforming growth factor beta stimulus	Histone deacetylase 2	Homo sapiens (human)
positive regulation of male mating behavior	Histone deacetylase 2	Homo sapiens (human)
negative regulation of stem cell population maintenance	Histone deacetylase 2	Homo sapiens (human)
positive regulation of stem cell population maintenance	Histone deacetylase 2	Homo sapiens (human)
cellular response to dopamine	Histone deacetylase 2	Homo sapiens (human)
response to amyloid-beta	Histone deacetylase 2	Homo sapiens (human)
regulation of stem cell differentiation	Histone deacetylase 2	Homo sapiens (human)
negative regulation of peptidyl-lysine acetylation	Histone deacetylase 2	Homo sapiens (human)
negative regulation of transcription by RNA polymerase II	Polyamine deacetylase HDAC10	Homo sapiens (human)
DNA repair	Polyamine deacetylase HDAC10	Homo sapiens (human)
chromatin organization	Polyamine deacetylase HDAC10	Homo sapiens (human)
regulation of DNA-templated transcription	Polyamine deacetylase HDAC10	Homo sapiens (human)
macroautophagy	Polyamine deacetylase HDAC10	Homo sapiens (human)
positive regulation of mismatch repair	Polyamine deacetylase HDAC10	Homo sapiens (human)
homologous recombination	Polyamine deacetylase HDAC10	Homo sapiens (human)
negative regulation of DNA-templated transcription	Polyamine deacetylase HDAC10	Homo sapiens (human)
polyamine deacetylation	Polyamine deacetylase HDAC10	Homo sapiens (human)
spermidine deacetylation	Polyamine deacetylase HDAC10	Homo sapiens (human)
epigenetic regulation of gene expression	Polyamine deacetylase HDAC10	Homo sapiens (human)
chromatin organization	Histone deacetylase 11	Homo sapiens (human)
oligodendrocyte development	Histone deacetylase 11	Homo sapiens (human)
epigenetic regulation of gene expression	Histone deacetylase 11	Homo sapiens (human)
negative regulation of transcription by RNA polymerase II	Histone deacetylase 8	Homo sapiens (human)
chromatin organization	Histone deacetylase 8	Homo sapiens (human)
mitotic sister chromatid cohesion	Histone deacetylase 8	Homo sapiens (human)
negative regulation of protein ubiquitination	Histone deacetylase 8	Homo sapiens (human)
regulation of protein stability	Histone deacetylase 8	Homo sapiens (human)
regulation of telomere maintenance	Histone deacetylase 8	Homo sapiens (human)
epigenetic regulation of gene expression	Histone deacetylase 8	Homo sapiens (human)
polyamine deacetylation	Histone deacetylase 6	Homo sapiens (human)
spermidine deacetylation	Histone deacetylase 6	Homo sapiens (human)
positive regulation of signaling receptor activity	Histone deacetylase 6	Homo sapiens (human)
protein polyubiquitination	Histone deacetylase 6	Homo sapiens (human)
response to amphetamine	Histone deacetylase 6	Homo sapiens (human)
protein deacetylation	Histone deacetylase 6	Homo sapiens (human)
protein quality control for misfolded or incompletely synthesized proteins	Histone deacetylase 6	Homo sapiens (human)
intracellular protein transport	Histone deacetylase 6	Homo sapiens (human)
autophagy	Histone deacetylase 6	Homo sapiens (human)
actin filament organization	Histone deacetylase 6	Homo sapiens (human)
negative regulation of microtubule depolymerization	Histone deacetylase 6	Homo sapiens (human)
regulation of autophagy	Histone deacetylase 6	Homo sapiens (human)
positive regulation of epithelial cell migration	Histone deacetylase 6	Homo sapiens (human)
negative regulation of hydrogen peroxide metabolic process	Histone deacetylase 6	Homo sapiens (human)
regulation of macroautophagy	Histone deacetylase 6	Homo sapiens (human)
axonal transport of mitochondrion	Histone deacetylase 6	Homo sapiens (human)
negative regulation of protein-containing complex assembly	Histone deacetylase 6	Homo sapiens (human)
regulation of protein stability	Histone deacetylase 6	Homo sapiens (human)
protein destabilization	Histone deacetylase 6	Homo sapiens (human)
lysosome localization	Histone deacetylase 6	Homo sapiens (human)
protein-containing complex disassembly	Histone deacetylase 6	Homo sapiens (human)
positive regulation of peptidyl-serine phosphorylation	Histone deacetylase 6	Homo sapiens (human)
cellular response to heat	Histone deacetylase 6	Homo sapiens (human)
peptidyl-lysine deacetylation	Histone deacetylase 6	Homo sapiens (human)
response to immobilization stress	Histone deacetylase 6	Homo sapiens (human)
cellular response to topologically incorrect protein	Histone deacetylase 6	Homo sapiens (human)
erythrocyte enucleation	Histone deacetylase 6	Homo sapiens (human)
ubiquitin-dependent protein catabolic process via the multivesicular body sorting pathway	Histone deacetylase 6	Homo sapiens (human)
negative regulation of protein-containing complex disassembly	Histone deacetylase 6	Homo sapiens (human)
regulation of fat cell differentiation	Histone deacetylase 6	Homo sapiens (human)
negative regulation of gene expression, epigenetic	Histone deacetylase 6	Homo sapiens (human)
negative regulation of proteolysis	Histone deacetylase 6	Homo sapiens (human)
negative regulation of DNA-templated transcription	Histone deacetylase 6	Homo sapiens (human)
collateral sprouting	Histone deacetylase 6	Homo sapiens (human)
negative regulation of axon extension involved in axon guidance	Histone deacetylase 6	Homo sapiens (human)
positive regulation of dendrite morphogenesis	Histone deacetylase 6	Homo sapiens (human)
negative regulation of oxidoreductase activity	Histone deacetylase 6	Homo sapiens (human)
response to corticosterone	Histone deacetylase 6	Homo sapiens (human)
response to misfolded protein	Histone deacetylase 6	Homo sapiens (human)
positive regulation of synaptic transmission, glutamatergic	Histone deacetylase 6	Homo sapiens (human)
cilium assembly	Histone deacetylase 6	Homo sapiens (human)
regulation of microtubule-based movement	Histone deacetylase 6	Homo sapiens (human)
regulation of androgen receptor signaling pathway	Histone deacetylase 6	Homo sapiens (human)
dendritic spine morphogenesis	Histone deacetylase 6	Homo sapiens (human)
cilium disassembly	Histone deacetylase 6	Homo sapiens (human)
parkin-mediated stimulation of mitophagy in response to mitochondrial depolarization	Histone deacetylase 6	Homo sapiens (human)
regulation of establishment of protein localization	Histone deacetylase 6	Homo sapiens (human)
cellular response to hydrogen peroxide	Histone deacetylase 6	Homo sapiens (human)
aggresome assembly	Histone deacetylase 6	Homo sapiens (human)
polyubiquitinated misfolded protein transport	Histone deacetylase 6	Homo sapiens (human)
response to growth factor	Histone deacetylase 6	Homo sapiens (human)
cellular response to misfolded protein	Histone deacetylase 6	Homo sapiens (human)
cellular response to parathyroid hormone stimulus	Histone deacetylase 6	Homo sapiens (human)
response to dexamethasone	Histone deacetylase 6	Homo sapiens (human)
tubulin deacetylation	Histone deacetylase 6	Homo sapiens (human)
positive regulation of tubulin deacetylation	Histone deacetylase 6	Homo sapiens (human)
positive regulation of cellular response to oxidative stress	Histone deacetylase 6	Homo sapiens (human)
negative regulation of protein acetylation	Histone deacetylase 6	Homo sapiens (human)
regulation of autophagy of mitochondrion	Histone deacetylase 6	Homo sapiens (human)
positive regulation of cholangiocyte proliferation	Histone deacetylase 6	Homo sapiens (human)
negative regulation of aggrephagy	Histone deacetylase 6	Homo sapiens (human)
epigenetic regulation of gene expression	Histone deacetylase 6	Homo sapiens (human)
negative regulation of transcription by RNA polymerase II	Histone deacetylase 9	Homo sapiens (human)
negative regulation of transcription by RNA polymerase II	Histone deacetylase 9	Homo sapiens (human)
negative regulation of cytokine production	Histone deacetylase 9	Homo sapiens (human)
response to amphetamine	Histone deacetylase 9	Homo sapiens (human)
inflammatory response	Histone deacetylase 9	Homo sapiens (human)
heart development	Histone deacetylase 9	Homo sapiens (human)
neuron differentiation	Histone deacetylase 9	Homo sapiens (human)
B cell differentiation	Histone deacetylase 9	Homo sapiens (human)
cellular response to insulin stimulus	Histone deacetylase 9	Homo sapiens (human)
peptidyl-lysine deacetylation	Histone deacetylase 9	Homo sapiens (human)
B cell activation	Histone deacetylase 9	Homo sapiens (human)
cholesterol homeostasis	Histone deacetylase 9	Homo sapiens (human)
negative regulation of gene expression, epigenetic	Histone deacetylase 9	Homo sapiens (human)
negative regulation of DNA-templated transcription	Histone deacetylase 9	Homo sapiens (human)
regulation of skeletal muscle fiber development	Histone deacetylase 9	Homo sapiens (human)
regulation of striated muscle cell differentiation	Histone deacetylase 9	Homo sapiens (human)
positive regulation of cell migration involved in sprouting angiogenesis	Histone deacetylase 9	Homo sapiens (human)
negative regulation of transcription by RNA polymerase II	Histone deacetylase 5	Homo sapiens (human)
negative regulation of transcription by RNA polymerase II	Histone deacetylase 5	Homo sapiens (human)
inflammatory response	Histone deacetylase 5	Homo sapiens (human)
response to xenobiotic stimulus	Histone deacetylase 5	Homo sapiens (human)
regulation of myotube differentiation	Histone deacetylase 5	Homo sapiens (human)
negative regulation of myotube differentiation	Histone deacetylase 5	Homo sapiens (human)
response to activity	Histone deacetylase 5	Homo sapiens (human)
neuron differentiation	Histone deacetylase 5	Homo sapiens (human)
B cell differentiation	Histone deacetylase 5	Homo sapiens (human)
cellular response to insulin stimulus	Histone deacetylase 5	Homo sapiens (human)
B cell activation	Histone deacetylase 5	Homo sapiens (human)
response to cocaine	Histone deacetylase 5	Homo sapiens (human)
regulation of protein binding	Histone deacetylase 5	Homo sapiens (human)
negative regulation of gene expression, epigenetic	Histone deacetylase 5	Homo sapiens (human)
negative regulation of DNA-templated transcription	Histone deacetylase 5	Homo sapiens (human)
positive regulation of transcription by RNA polymerase II	Histone deacetylase 5	Homo sapiens (human)
positive regulation of DNA-binding transcription factor activity	Histone deacetylase 5	Homo sapiens (human)
cellular response to lipopolysaccharide	Histone deacetylase 5	Homo sapiens (human)
negative regulation of cell migration involved in sprouting angiogenesis	Histone deacetylase 5	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
transcription corepressor binding	Histone deacetylase 3	Homo sapiens (human)
chromatin binding	Histone deacetylase 3	Homo sapiens (human)
transcription corepressor activity	Histone deacetylase 3	Homo sapiens (human)
histone deacetylase activity	Histone deacetylase 3	Homo sapiens (human)
protein binding	Histone deacetylase 3	Homo sapiens (human)
enzyme binding	Histone deacetylase 3	Homo sapiens (human)
cyclin binding	Histone deacetylase 3	Homo sapiens (human)
chromatin DNA binding	Histone deacetylase 3	Homo sapiens (human)
protein lysine deacetylase activity	Histone deacetylase 3	Homo sapiens (human)
histone deacetylase binding	Histone deacetylase 3	Homo sapiens (human)
NF-kappaB binding	Histone deacetylase 3	Homo sapiens (human)
DNA-binding transcription factor binding	Histone deacetylase 3	Homo sapiens (human)
protein decrotonylase activity	Histone deacetylase 3	Homo sapiens (human)
histone decrotonylase activity	Histone deacetylase 3	Homo sapiens (human)
protein de-2-hydroxyisobutyrylase activity	Histone deacetylase 3	Homo sapiens (human)
retinal dehydrogenase activity	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
aldo-keto reductase (NADPH) activity	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
protein binding	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
alcohol dehydrogenase (NADP+) activity	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
geranylgeranyl reductase activity	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
allyl-alcohol dehydrogenase activity	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
indanol dehydrogenase activity	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
all-trans-retinol dehydrogenase (NADP+) activity	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
aldose reductase (NADPH) activity	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
guanyl-nucleotide exchange factor activity	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
protein binding	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
protein domain specific binding	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
cAMP binding	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA binding	Amyloid-beta precursor protein	Homo sapiens (human)
DNA binding	Amyloid-beta precursor protein	Homo sapiens (human)
serine-type endopeptidase inhibitor activity	Amyloid-beta precursor protein	Homo sapiens (human)
signaling receptor binding	Amyloid-beta precursor protein	Homo sapiens (human)
protein binding	Amyloid-beta precursor protein	Homo sapiens (human)
heparin binding	Amyloid-beta precursor protein	Homo sapiens (human)
enzyme binding	Amyloid-beta precursor protein	Homo sapiens (human)
identical protein binding	Amyloid-beta precursor protein	Homo sapiens (human)
transition metal ion binding	Amyloid-beta precursor protein	Homo sapiens (human)
receptor ligand activity	Amyloid-beta precursor protein	Homo sapiens (human)
PTB domain binding	Amyloid-beta precursor protein	Homo sapiens (human)
protein serine/threonine kinase binding	Amyloid-beta precursor protein	Homo sapiens (human)
signaling receptor activator activity	Amyloid-beta precursor protein	Homo sapiens (human)
3'-5'-RNA exonuclease activity	Replicase polyprotein 1ab	Severe acute respiratory syndrome-related coronavirus
RNA-dependent RNA polymerase activity	Replicase polyprotein 1ab	Severe acute respiratory syndrome-related coronavirus
cysteine-type endopeptidase activity	Replicase polyprotein 1ab	Severe acute respiratory syndrome-related coronavirus
mRNA 5'-cap (guanine-N7-)-methyltransferase activity	Replicase polyprotein 1ab	Severe acute respiratory syndrome-related coronavirus
mRNA (nucleoside-2'-O-)-methyltransferase activity	Replicase polyprotein 1ab	Severe acute respiratory syndrome-related coronavirus
5'-3' RNA helicase activity	Replicase polyprotein 1ab	Severe acute respiratory syndrome-related coronavirus
K63-linked deubiquitinase activity	Replicase polyprotein 1ab	Severe acute respiratory syndrome-related coronavirus
K48-linked deubiquitinase activity	Replicase polyprotein 1ab	Severe acute respiratory syndrome-related coronavirus
3'-5'-RNA exonuclease activity	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2
RNA-dependent RNA polymerase activity	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2
cysteine-type endopeptidase activity	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2
mRNA 5'-cap (guanine-N7-)-methyltransferase activity	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2
mRNA (nucleoside-2'-O-)-methyltransferase activity	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2
mRNA guanylyltransferase activity	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2
RNA endonuclease activity, producing 3'-phosphomonoesters	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2
ISG15-specific peptidase activity	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2
5'-3' RNA helicase activity	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2
protein guanylyltransferase activity	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2
retinal dehydrogenase activity	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
aldose reductase (NADPH) activity	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
protein binding	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
electron transfer activity	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
prostaglandin H2 endoperoxidase reductase activity	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
glyceraldehyde oxidoreductase activity	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
allyl-alcohol dehydrogenase activity	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
L-glucuronate reductase activity	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
glycerol dehydrogenase [NADP+] activity	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
all-trans-retinol dehydrogenase (NADP+) activity	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
protein tyrosine phosphatase activity	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
integrin binding	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
protein binding	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
protein kinase binding	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
syntaxin binding	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
receptor tyrosine kinase binding	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
STAT family protein binding	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
non-membrane spanning protein tyrosine phosphatase activity	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
RNA binding	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
protein tyrosine phosphatase activity	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
insulin receptor binding	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
protein binding	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
zinc ion binding	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
enzyme binding	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
protein kinase binding	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
receptor tyrosine kinase binding	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
cadherin binding	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
ephrin receptor binding	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
protein phosphatase 2A binding	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
non-membrane spanning protein tyrosine phosphatase activity	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
transcription cis-regulatory region binding	Histone deacetylase 4	Homo sapiens (human)
histone binding	Histone deacetylase 4	Homo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA binding	Histone deacetylase 4	Homo sapiens (human)
histone deacetylase activity	Histone deacetylase 4	Homo sapiens (human)
protein binding	Histone deacetylase 4	Homo sapiens (human)
zinc ion binding	Histone deacetylase 4	Homo sapiens (human)
SUMO transferase activity	Histone deacetylase 4	Homo sapiens (human)
potassium ion binding	Histone deacetylase 4	Homo sapiens (human)
protein lysine deacetylase activity	Histone deacetylase 4	Homo sapiens (human)
identical protein binding	Histone deacetylase 4	Homo sapiens (human)
histone deacetylase binding	Histone deacetylase 4	Homo sapiens (human)
molecular adaptor activity	Histone deacetylase 4	Homo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor binding	Histone deacetylase 4	Homo sapiens (human)
DNA-binding transcription factor binding	Histone deacetylase 4	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)
nucleosomal DNA binding	Histone deacetylase 1	Homo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA binding	Histone deacetylase 1	Homo sapiens (human)
RNA polymerase II core promoter sequence-specific DNA binding	Histone deacetylase 1	Homo sapiens (human)
core promoter sequence-specific DNA binding	Histone deacetylase 1	Homo sapiens (human)
transcription corepressor binding	Histone deacetylase 1	Homo sapiens (human)
p53 binding	Histone deacetylase 1	Homo sapiens (human)
transcription corepressor activity	Histone deacetylase 1	Homo sapiens (human)
histone deacetylase activity	Histone deacetylase 1	Homo sapiens (human)
protein binding	Histone deacetylase 1	Homo sapiens (human)
enzyme binding	Histone deacetylase 1	Homo sapiens (human)
protein lysine deacetylase activity	Histone deacetylase 1	Homo sapiens (human)
Krueppel-associated box domain binding	Histone deacetylase 1	Homo sapiens (human)
histone deacetylase binding	Histone deacetylase 1	Homo sapiens (human)
NF-kappaB binding	Histone deacetylase 1	Homo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor binding	Histone deacetylase 1	Homo sapiens (human)
E-box binding	Histone deacetylase 1	Homo sapiens (human)
DNA-binding transcription factor binding	Histone deacetylase 1	Homo sapiens (human)
histone decrotonylase activity	Histone deacetylase 1	Homo sapiens (human)
promoter-specific chromatin binding	Histone deacetylase 1	Homo sapiens (human)
chromatin binding	Histone deacetylase 7	Homo sapiens (human)
transcription corepressor activity	Histone deacetylase 7	Homo sapiens (human)
histone deacetylase activity	Histone deacetylase 7	Homo sapiens (human)
protein kinase C binding	Histone deacetylase 7	Homo sapiens (human)
protein binding	Histone deacetylase 7	Homo sapiens (human)
SUMO transferase activity	Histone deacetylase 7	Homo sapiens (human)
protein kinase binding	Histone deacetylase 7	Homo sapiens (human)
protein lysine deacetylase activity	Histone deacetylase 7	Homo sapiens (human)
metal ion binding	Histone deacetylase 7	Homo sapiens (human)
14-3-3 protein binding	Histone deacetylase 7	Homo sapiens (human)
DNA-binding transcription factor binding	Histone deacetylase 7	Homo sapiens (human)
guanyl-nucleotide exchange factor activity	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
protein binding	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
cAMP binding	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
protein-macromolecule adaptor activity	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
small GTPase binding	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
nucleosomal DNA binding	Histone deacetylase 2	Homo sapiens (human)
chromatin binding	Histone deacetylase 2	Homo sapiens (human)
RNA binding	Histone deacetylase 2	Homo sapiens (human)
histone deacetylase activity	Histone deacetylase 2	Homo sapiens (human)
protein binding	Histone deacetylase 2	Homo sapiens (human)
enzyme binding	Histone deacetylase 2	Homo sapiens (human)
heat shock protein binding	Histone deacetylase 2	Homo sapiens (human)
protein lysine deacetylase activity	Histone deacetylase 2	Homo sapiens (human)
histone binding	Histone deacetylase 2	Homo sapiens (human)
histone deacetylase binding	Histone deacetylase 2	Homo sapiens (human)
NF-kappaB binding	Histone deacetylase 2	Homo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor binding	Histone deacetylase 2	Homo sapiens (human)
histone decrotonylase activity	Histone deacetylase 2	Homo sapiens (human)
protein de-2-hydroxyisobutyrylase activity	Histone deacetylase 2	Homo sapiens (human)
promoter-specific chromatin binding	Histone deacetylase 2	Homo sapiens (human)
protein lysine deacetylase activity	Polyamine deacetylase HDAC10	Homo sapiens (human)
histone deacetylase activity	Polyamine deacetylase HDAC10	Homo sapiens (human)
protein binding	Polyamine deacetylase HDAC10	Homo sapiens (human)
zinc ion binding	Polyamine deacetylase HDAC10	Homo sapiens (human)
deacetylase activity	Polyamine deacetylase HDAC10	Homo sapiens (human)
enzyme binding	Polyamine deacetylase HDAC10	Homo sapiens (human)
protein lysine deacetylase activity	Polyamine deacetylase HDAC10	Homo sapiens (human)
histone deacetylase binding	Polyamine deacetylase HDAC10	Homo sapiens (human)
acetylputrescine deacetylase activity	Polyamine deacetylase HDAC10	Homo sapiens (human)
acetylspermidine deacetylase activity	Polyamine deacetylase HDAC10	Homo sapiens (human)
histone deacetylase activity	Histone deacetylase 11	Homo sapiens (human)
protein binding	Histone deacetylase 11	Homo sapiens (human)
DNA-binding transcription factor binding	Histone deacetylase 11	Homo sapiens (human)
histone deacetylase activity	Histone deacetylase 8	Homo sapiens (human)
protein binding	Histone deacetylase 8	Homo sapiens (human)
Hsp70 protein binding	Histone deacetylase 8	Homo sapiens (human)
protein lysine deacetylase activity	Histone deacetylase 8	Homo sapiens (human)
metal ion binding	Histone deacetylase 8	Homo sapiens (human)
Hsp90 protein binding	Histone deacetylase 8	Homo sapiens (human)
DNA-binding transcription factor binding	Histone deacetylase 8	Homo sapiens (human)
histone decrotonylase activity	Histone deacetylase 8	Homo sapiens (human)
acetylspermidine deacetylase activity	Histone deacetylase 6	Homo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA binding	Histone deacetylase 6	Homo sapiens (human)
transcription corepressor binding	Histone deacetylase 6	Homo sapiens (human)
actin binding	Histone deacetylase 6	Homo sapiens (human)
histone deacetylase activity	Histone deacetylase 6	Homo sapiens (human)
protein binding	Histone deacetylase 6	Homo sapiens (human)
beta-catenin binding	Histone deacetylase 6	Homo sapiens (human)
microtubule binding	Histone deacetylase 6	Homo sapiens (human)
zinc ion binding	Histone deacetylase 6	Homo sapiens (human)
enzyme binding	Histone deacetylase 6	Homo sapiens (human)
polyubiquitin modification-dependent protein binding	Histone deacetylase 6	Homo sapiens (human)
ubiquitin protein ligase binding	Histone deacetylase 6	Homo sapiens (human)
protein lysine deacetylase activity	Histone deacetylase 6	Homo sapiens (human)
histone deacetylase binding	Histone deacetylase 6	Homo sapiens (human)
tubulin deacetylase activity	Histone deacetylase 6	Homo sapiens (human)
alpha-tubulin binding	Histone deacetylase 6	Homo sapiens (human)
ubiquitin binding	Histone deacetylase 6	Homo sapiens (human)
tau protein binding	Histone deacetylase 6	Homo sapiens (human)
beta-tubulin binding	Histone deacetylase 6	Homo sapiens (human)
misfolded protein binding	Histone deacetylase 6	Homo sapiens (human)
Hsp90 protein binding	Histone deacetylase 6	Homo sapiens (human)
dynein complex binding	Histone deacetylase 6	Homo sapiens (human)
transcription factor binding	Histone deacetylase 6	Homo sapiens (human)
transcription corepressor activity	Histone deacetylase 9	Homo sapiens (human)
histone deacetylase activity	Histone deacetylase 9	Homo sapiens (human)
protein kinase C binding	Histone deacetylase 9	Homo sapiens (human)
protein binding	Histone deacetylase 9	Homo sapiens (human)
histone H3K14 deacetylase activity	Histone deacetylase 9	Homo sapiens (human)
histone H3K9 deacetylase activity	Histone deacetylase 9	Homo sapiens (human)
protein lysine deacetylase activity	Histone deacetylase 9	Homo sapiens (human)
histone H4K16 deacetylase activity	Histone deacetylase 9	Homo sapiens (human)
histone deacetylase binding	Histone deacetylase 9	Homo sapiens (human)
metal ion binding	Histone deacetylase 9	Homo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor binding	Histone deacetylase 9	Homo sapiens (human)
DNA-binding transcription factor binding	Histone deacetylase 9	Homo sapiens (human)
transcription cis-regulatory region binding	Histone deacetylase 5	Homo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA binding	Histone deacetylase 5	Homo sapiens (human)
transcription corepressor binding	Histone deacetylase 5	Homo sapiens (human)
chromatin binding	Histone deacetylase 5	Homo sapiens (human)
histone deacetylase activity	Histone deacetylase 5	Homo sapiens (human)
protein kinase C binding	Histone deacetylase 5	Homo sapiens (human)
protein binding	Histone deacetylase 5	Homo sapiens (human)
protein lysine deacetylase activity	Histone deacetylase 5	Homo sapiens (human)
identical protein binding	Histone deacetylase 5	Homo sapiens (human)
histone deacetylase binding	Histone deacetylase 5	Homo sapiens (human)
metal ion binding	Histone deacetylase 5	Homo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor binding	Histone deacetylase 5	Homo sapiens (human)
DNA-binding transcription factor binding	Histone deacetylase 5	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
nucleus	Histone deacetylase 3	Homo sapiens (human)
nucleoplasm	Histone deacetylase 3	Homo sapiens (human)
cytoplasm	Histone deacetylase 3	Homo sapiens (human)
Golgi apparatus	Histone deacetylase 3	Homo sapiens (human)
cytosol	Histone deacetylase 3	Homo sapiens (human)
plasma membrane	Histone deacetylase 3	Homo sapiens (human)
mitotic spindle	Histone deacetylase 3	Homo sapiens (human)
histone deacetylase complex	Histone deacetylase 3	Homo sapiens (human)
transcription repressor complex	Histone deacetylase 3	Homo sapiens (human)
nucleus	Histone deacetylase 3	Homo sapiens (human)
extracellular region	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
lysosome	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
cytosol	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
cytosol	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
mitochondrion	Aldo-keto reductase family 1 member B10	Homo sapiens (human)
plasma membrane	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
cortical actin cytoskeleton	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
plasma membrane	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
microvillus	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
endomembrane system	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
membrane	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
lamellipodium	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
filopodium	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
extracellular exosome	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
extracellular space	Amyloid-beta precursor protein	Homo sapiens (human)
dendrite	Amyloid-beta precursor protein	Homo sapiens (human)
extracellular region	Amyloid-beta precursor protein	Homo sapiens (human)
extracellular space	Amyloid-beta precursor protein	Homo sapiens (human)
nuclear envelope lumen	Amyloid-beta precursor protein	Homo sapiens (human)
cytoplasm	Amyloid-beta precursor protein	Homo sapiens (human)
mitochondrial inner membrane	Amyloid-beta precursor protein	Homo sapiens (human)
endosome	Amyloid-beta precursor protein	Homo sapiens (human)
early endosome	Amyloid-beta precursor protein	Homo sapiens (human)
endoplasmic reticulum	Amyloid-beta precursor protein	Homo sapiens (human)
endoplasmic reticulum lumen	Amyloid-beta precursor protein	Homo sapiens (human)
smooth endoplasmic reticulum	Amyloid-beta precursor protein	Homo sapiens (human)
Golgi apparatus	Amyloid-beta precursor protein	Homo sapiens (human)
Golgi lumen	Amyloid-beta precursor protein	Homo sapiens (human)
Golgi-associated vesicle	Amyloid-beta precursor protein	Homo sapiens (human)
cytosol	Amyloid-beta precursor protein	Homo sapiens (human)
plasma membrane	Amyloid-beta precursor protein	Homo sapiens (human)
clathrin-coated pit	Amyloid-beta precursor protein	Homo sapiens (human)
cell-cell junction	Amyloid-beta precursor protein	Homo sapiens (human)
synaptic vesicle	Amyloid-beta precursor protein	Homo sapiens (human)
cell surface	Amyloid-beta precursor protein	Homo sapiens (human)
membrane	Amyloid-beta precursor protein	Homo sapiens (human)
COPII-coated ER to Golgi transport vesicle	Amyloid-beta precursor protein	Homo sapiens (human)
axon	Amyloid-beta precursor protein	Homo sapiens (human)
growth cone	Amyloid-beta precursor protein	Homo sapiens (human)
platelet alpha granule lumen	Amyloid-beta precursor protein	Homo sapiens (human)
neuromuscular junction	Amyloid-beta precursor protein	Homo sapiens (human)
endosome lumen	Amyloid-beta precursor protein	Homo sapiens (human)
trans-Golgi network membrane	Amyloid-beta precursor protein	Homo sapiens (human)
ciliary rootlet	Amyloid-beta precursor protein	Homo sapiens (human)
dendritic spine	Amyloid-beta precursor protein	Homo sapiens (human)
dendritic shaft	Amyloid-beta precursor protein	Homo sapiens (human)
perikaryon	Amyloid-beta precursor protein	Homo sapiens (human)
membrane raft	Amyloid-beta precursor protein	Homo sapiens (human)
apical part of cell	Amyloid-beta precursor protein	Homo sapiens (human)
synapse	Amyloid-beta precursor protein	Homo sapiens (human)
perinuclear region of cytoplasm	Amyloid-beta precursor protein	Homo sapiens (human)
presynaptic active zone	Amyloid-beta precursor protein	Homo sapiens (human)
spindle midzone	Amyloid-beta precursor protein	Homo sapiens (human)
recycling endosome	Amyloid-beta precursor protein	Homo sapiens (human)
extracellular exosome	Amyloid-beta precursor protein	Homo sapiens (human)
receptor complex	Amyloid-beta precursor protein	Homo sapiens (human)
early endosome	Amyloid-beta precursor protein	Homo sapiens (human)
membrane raft	Amyloid-beta precursor protein	Homo sapiens (human)
cell surface	Amyloid-beta precursor protein	Homo sapiens (human)
Golgi apparatus	Amyloid-beta precursor protein	Homo sapiens (human)
plasma membrane	Amyloid-beta precursor protein	Homo sapiens (human)
double membrane vesicle viral factory outer membrane	Replicase polyprotein 1ab	Severe acute respiratory syndrome-related coronavirus
double membrane vesicle viral factory outer membrane	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2
extracellular space	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
nucleoplasm	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
cytosol	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
extracellular exosome	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
cytosol	Aldo-keto reductase family 1 member B1	Homo sapiens (human)
plasma membrane	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
nucleoplasm	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
endoplasmic reticulum	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
endoplasmic reticulum-Golgi intermediate compartment	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
cytosol	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
endosome lumen	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
cytoplasm	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
nucleus	Tyrosine-protein phosphatase non-receptor type 2	Homo sapiens (human)
plasma membrane	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
cytoplasm	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
mitochondrial matrix	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
early endosome	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
endoplasmic reticulum	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
cytosol	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
mitochondrial crista	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
endosome lumen	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
sorting endosome	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
cytoplasmic side of endoplasmic reticulum membrane	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
protein-containing complex	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
endoplasmic reticulum	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
cytoplasm	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
early endosome	Tyrosine-protein phosphatase non-receptor type 1	Homo sapiens (human)
nucleus	Histone deacetylase 4	Homo sapiens (human)
nucleoplasm	Histone deacetylase 4	Homo sapiens (human)
cytoplasm	Histone deacetylase 4	Homo sapiens (human)
cytosol	Histone deacetylase 4	Homo sapiens (human)
nuclear speck	Histone deacetylase 4	Homo sapiens (human)
histone deacetylase complex	Histone deacetylase 4	Homo sapiens (human)
chromatin	Histone deacetylase 4	Homo sapiens (human)
transcription repressor complex	Histone deacetylase 4	Homo sapiens (human)
extracellular space	Lactoperoxidase	Bos taurus (cattle)
cytoplasm	Lactoperoxidase	Bos taurus (cattle)
nucleus	Histone deacetylase 1	Homo sapiens (human)
nucleoplasm	Histone deacetylase 1	Homo sapiens (human)
cytoplasm	Histone deacetylase 1	Homo sapiens (human)
cytosol	Histone deacetylase 1	Homo sapiens (human)
NuRD complex	Histone deacetylase 1	Homo sapiens (human)
neuronal cell body	Histone deacetylase 1	Homo sapiens (human)
Sin3-type complex	Histone deacetylase 1	Homo sapiens (human)
histone deacetylase complex	Histone deacetylase 1	Homo sapiens (human)
chromatin	Histone deacetylase 1	Homo sapiens (human)
heterochromatin	Histone deacetylase 1	Homo sapiens (human)
transcription repressor complex	Histone deacetylase 1	Homo sapiens (human)
protein-containing complex	Histone deacetylase 1	Homo sapiens (human)
nucleus	Histone deacetylase 1	Homo sapiens (human)
nucleus	Histone deacetylase 7	Homo sapiens (human)
nucleoplasm	Histone deacetylase 7	Homo sapiens (human)
cytoplasm	Histone deacetylase 7	Homo sapiens (human)
cytosol	Histone deacetylase 7	Homo sapiens (human)
cytosol	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
plasma membrane	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
membrane	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
hippocampal mossy fiber to CA3 synapse	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
plasma membrane	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
chromosome, telomeric region	Histone deacetylase 2	Homo sapiens (human)
nucleus	Histone deacetylase 2	Homo sapiens (human)
nucleoplasm	Histone deacetylase 2	Homo sapiens (human)
cytoplasm	Histone deacetylase 2	Homo sapiens (human)
NuRD complex	Histone deacetylase 2	Homo sapiens (human)
Sin3-type complex	Histone deacetylase 2	Homo sapiens (human)
histone deacetylase complex	Histone deacetylase 2	Homo sapiens (human)
chromatin	Histone deacetylase 2	Homo sapiens (human)
protein-containing complex	Histone deacetylase 2	Homo sapiens (human)
ESC/E(Z) complex	Histone deacetylase 2	Homo sapiens (human)
nucleus	Histone deacetylase 2	Homo sapiens (human)
nucleus	Polyamine deacetylase HDAC10	Homo sapiens (human)
nucleoplasm	Polyamine deacetylase HDAC10	Homo sapiens (human)
cytoplasm	Polyamine deacetylase HDAC10	Homo sapiens (human)
cytosol	Polyamine deacetylase HDAC10	Homo sapiens (human)
intracellular membrane-bounded organelle	Polyamine deacetylase HDAC10	Homo sapiens (human)
histone deacetylase complex	Polyamine deacetylase HDAC10	Homo sapiens (human)
nucleus	Histone deacetylase 11	Homo sapiens (human)
plasma membrane	Histone deacetylase 11	Homo sapiens (human)
histone deacetylase complex	Histone deacetylase 11	Homo sapiens (human)
nuclear chromosome	Histone deacetylase 8	Homo sapiens (human)
nucleus	Histone deacetylase 8	Homo sapiens (human)
nucleoplasm	Histone deacetylase 8	Homo sapiens (human)
cytoplasm	Histone deacetylase 8	Homo sapiens (human)
histone deacetylase complex	Histone deacetylase 8	Homo sapiens (human)
nucleus	Histone deacetylase 8	Homo sapiens (human)
nucleus	Histone deacetylase 6	Homo sapiens (human)
nucleoplasm	Histone deacetylase 6	Homo sapiens (human)
cytoplasm	Histone deacetylase 6	Homo sapiens (human)
multivesicular body	Histone deacetylase 6	Homo sapiens (human)
centrosome	Histone deacetylase 6	Homo sapiens (human)
cytosol	Histone deacetylase 6	Homo sapiens (human)
microtubule	Histone deacetylase 6	Homo sapiens (human)
caveola	Histone deacetylase 6	Homo sapiens (human)
inclusion body	Histone deacetylase 6	Homo sapiens (human)
aggresome	Histone deacetylase 6	Homo sapiens (human)
axon	Histone deacetylase 6	Homo sapiens (human)
dendrite	Histone deacetylase 6	Homo sapiens (human)
cell leading edge	Histone deacetylase 6	Homo sapiens (human)
ciliary basal body	Histone deacetylase 6	Homo sapiens (human)
perikaryon	Histone deacetylase 6	Homo sapiens (human)
perinuclear region of cytoplasm	Histone deacetylase 6	Homo sapiens (human)
axon cytoplasm	Histone deacetylase 6	Homo sapiens (human)
histone deacetylase complex	Histone deacetylase 6	Homo sapiens (human)
microtubule associated complex	Histone deacetylase 6	Homo sapiens (human)
nucleus	Histone deacetylase 9	Homo sapiens (human)
nucleoplasm	Histone deacetylase 9	Homo sapiens (human)
cytoplasm	Histone deacetylase 9	Homo sapiens (human)
histone deacetylase complex	Histone deacetylase 9	Homo sapiens (human)
transcription regulator complex	Histone deacetylase 9	Homo sapiens (human)
histone methyltransferase complex	Histone deacetylase 9	Homo sapiens (human)
nucleus	Histone deacetylase 5	Homo sapiens (human)
nucleoplasm	Histone deacetylase 5	Homo sapiens (human)
cytoplasm	Histone deacetylase 5	Homo sapiens (human)
Golgi apparatus	Histone deacetylase 5	Homo sapiens (human)
cytosol	Histone deacetylase 5	Homo sapiens (human)
nuclear speck	Histone deacetylase 5	Homo sapiens (human)
histone deacetylase complex	Histone deacetylase 5	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Assay ID	Title	Year	Journal	Article
AID1172639	Inhibition of cell proliferation of human U251 cells assessed as cell viability at 100 uM after 72 hrs by sulforhodamine B assay	2014	Bioorganic & medicinal chemistry letters, Nov-15, Volume: 24, Issue:22	Bioactive triterpenoid saponins and phenolic compounds against glioma cells.
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.
AID1374941	Selectivity index, ratio of IC50 for TCPTP (unknown origin) to IC50 for PTP1B (unknown origin)	2018	Bioorganic & medicinal chemistry letters, 04-15, Volume: 28, Issue:7	Identification of caffeoylquinic acid derivatives as natural protein tyrosine phosphatase 1B inhibitors from Artemisia princeps.
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.
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.
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.
AID1374937	Selectivity index, ratio of inhibition of PTP1B (unknown origin) to inhibition of VHR (unknown origin)	2018	Bioorganic & medicinal chemistry letters, 04-15, Volume: 28, Issue:7	Identification of caffeoylquinic acid derivatives as natural protein tyrosine phosphatase 1B inhibitors from Artemisia princeps.
AID379093	Growth inhibition of BALB/c mouse cloned 3T3/A31 cells at 100 ug/mL after 72 hrs by nigrosin assay	1999	Journal of natural products, Mar, Volume: 62, Issue:3	Activities of plant-derived phenols in a fibroblast cell culture model
AID379093	Growth inhibition of BALB/c mouse cloned 3T3/A31 cells at 100 ug/mL after 72 hrs by nigrosin assay	1999	Journal of natural products, Mar, Volume: 62, Issue:3	Activities of plant-derived phenols in a fibroblast cell culture model.
AID378766	Induction of resting HMNC proliferation assessed as [3H]thymidine uptake after 3 days by lymphoproliferation test	1999	Journal of natural products, Mar, Volume: 62, Issue:3	Immunomodulatory principles of Dichrocephala bicolor.
AID91425	Inhibition of HIV-1 integrase, under 1 uM for the 3''-preprocessing	2000	Journal of medicinal chemistry, Jun-01, Volume: 43, Issue:11	Developing a dynamic pharmacophore model for HIV-1 integrase.
AID397153	Antioxidant activity against Cu2+-induced lipid peroxidation in human plasma LDL 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.
AID1374931	Inhibition of PTP1B (unknown origin) at 100 uM relative to control	2018	Bioorganic & medicinal chemistry letters, 04-15, Volume: 28, Issue:7	Identification of caffeoylquinic acid derivatives as natural protein tyrosine phosphatase 1B inhibitors from Artemisia princeps.
AID1374930	Non-competitive inhibition of PTP1B (unknown origin) using p-NPP as substrate by Lineweaver-Burk plot analysis	2018	Bioorganic & medicinal chemistry letters, 04-15, Volume: 28, Issue:7	Identification of caffeoylquinic acid derivatives as natural protein tyrosine phosphatase 1B inhibitors from Artemisia princeps.
AID718323	Antioxidant activity assessed as trolox equivalents of ABTS radical scavenging activity at 15 mins by TEAC assay	2012	Journal of natural products, Dec-28, Volume: 75, Issue:12	Antioxidant glucosylated caffeoylquinic acid derivatives in the invasive tropical soda apple, Solanum viarum.
AID580002	Antiobesity activity against high-fat diet fed ICR mouse assessed as change in food intake per day after 4 weeks (high fat diet fed group = 5.51 +/- 0.20 g/day)	2011	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 21, Issue:6	Anti-obesity compounds in green leaves of Eucommia ulmoides.
AID718317	Antioxidant activity assessed as DPPH radical scavenging activity	2012	Journal of natural products, Dec-28, Volume: 75, Issue:12	Antioxidant glucosylated caffeoylquinic acid derivatives in the invasive tropical soda apple, Solanum viarum.
AID1766076	Inhibition of preadipocyte differentiation in mouse 3T3-L1 cells assessed as lipid droplet accumulation at 100 uM incubated for 8 days by Oil Red O staining method relative to untreated control	2021	Bioorganic & medicinal chemistry letters, 10-01, Volume: 49	Phytochemicals from the flowers of Prunus persica (L.) Batsch: Anti-adipogenic effect of mandelamide on 3T3-L1 preadipocytes.
AID91561	Percentage inhibition of compound against 3'-processing of HIV-1 integrase at 100 ug/mL	1997	Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6	Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching.
AID1569185	Inhibition of M-CSF/RANKL-induced osteoclast differentiation in C57BL/6 mouse bone marrow macrophage assessed as reduction in multinucleated TRAP+ cells incubated for 6 days with fresh media replacement on day 3 and measured on day 6 by TRAP staining-base
AID1326319	Antibacterial activity against Klebsiella pneumoniae ATCC BAA-1144 after 18 hrs by broth microdilution method	2016	Bioorganic & medicinal chemistry, 12-15, Volume: 24, Issue:24	Recent advances in the discovery and development of antibacterial agents targeting the cell-division protein FtsZ.
AID1151282	Bactericidal activity against BacLight Green labeled Escherichia coli up to 30 ug/ml	2014	Journal of natural products, May-23, Volume: 77, Issue:5	Development of a fluorometric microplate antiadhesion assay using uropathogenic Escherichia coli and human uroepithelial cells.
AID1460718	Neuroprotective activity in human SH-SY5Y cells assessed as reduction in glutamate-induced cytotoxicity at 10 uM relative to untreated control	2017	Journal of natural products, 04-28, Volume: 80, Issue:4	Neuroprotective Caffeoylquinic Acid Derivatives from the Flowers of Chrysanthemum morifolium.
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.
AID718454	Antioxidant activity assessed as trolox equivalents of ABTS radical scavenging activity at 10 mins by TEAC assay	2012	Journal of natural products, Dec-28, Volume: 75, Issue:12	Antioxidant glucosylated caffeoylquinic acid derivatives in the invasive tropical soda apple, Solanum viarum.
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.
AID1374934	Inhibition of SHP1 (unknown origin) at 100 uM relative to control	2018	Bioorganic & medicinal chemistry letters, 04-15, Volume: 28, Issue:7	Identification of caffeoylquinic acid derivatives as natural protein tyrosine phosphatase 1B inhibitors from Artemisia princeps.
AID1256762	Inhibition of Mycobacterium tuberculosis MTCC 300 DAH7PS expressed in Escherichia coli BL21 (DE3) using 25 to 125 uM PEP/100 uM E4P as substrate at 10 uM by spectrophotometric analysis relative to control	2015	European journal of medicinal chemistry, Nov-13, Volume: 105	Inhibition of 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase from Mycobacterium tuberculosis: in silico screening and in vitro validation.
AID1420910	Antioxidant activity assessed as DPPH free radical scavenging activity	2018	European journal of medicinal chemistry, Oct-05, Volume: 158	Antibacterial and antioxidant activities for natural and synthetic dual-active compounds.
AID378767	Immunomodulatory activity in resting HMNC assessed as IFN-gamma production at 10 ug/mL after 3 days by EIA realtive to control	1999	Journal of natural products, Mar, Volume: 62, Issue:3	Immunomodulatory principles of Dichrocephala bicolor.
AID718320	Antioxidant activity assessed as trolox equivalents of ABTS radical scavenging activity at 35 mins by TEAC assay	2012	Journal of natural products, Dec-28, Volume: 75, Issue:12	Antioxidant glucosylated caffeoylquinic acid derivatives in the invasive tropical soda apple, Solanum viarum.
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.
AID624609	Specific activity of expressed human recombinant UGT1A6	2000	Annual review of pharmacology and toxicology, , Volume: 40	Human UDP-glucuronosyltransferases: metabolism, expression, and disease.
AID1056520	Antiinflammatory activity in rat polymorphonuclear leukocytes assessed as inhibition of PAF-induced release of glucuronidase at 10 uM	2013	Journal of natural products, Dec-27, Volume: 76, Issue:12	Homosecoiridoid alkaloids with amino acid units from the flower buds of Lonicera japonica.
AID1374932	Inhibition of TCPTP (unknown origin) at 100 uM relative to control	2018	Bioorganic & medicinal chemistry letters, 04-15, Volume: 28, Issue:7	Identification of caffeoylquinic acid derivatives as natural protein tyrosine phosphatase 1B inhibitors from Artemisia princeps.
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.
AID1705065	Inhibition of biotinylated 5-(4-((Z)-3-Carboxy-3-hydroxyacryloyl)-4-(4-chlorobenzyl)piperidine-1-carbonyl)-2-((13,35-dioxo-39-((3aR,4R,6aS)-2-oxohexahydro-1H-thieno[3,4-d]imidazole-4-yl)-3,6,9,16,19,22,25,28,31-nonaoxa-12,34-diazanonatriacontyl)oxy)benzoi	2020	European journal of medicinal chemistry, Dec-15, Volume: 208	Unraveling the anti-influenza effect of flavonoids: Experimental validation of luteolin and its congeners as potent influenza endonuclease inhibitors.
AID1374935	Inhibition of SHP2 (unknown origin) at 100 uM relative to control	2018	Bioorganic & medicinal chemistry letters, 04-15, Volume: 28, Issue:7	Identification of caffeoylquinic acid derivatives as natural protein tyrosine phosphatase 1B inhibitors from Artemisia princeps.
AID378770	Immunomodulatory activity in resting HMNC assessed as IFN-gamma production after 3 days by EIA	1999	Journal of natural products, Mar, Volume: 62, Issue:3	Immunomodulatory principles of Dichrocephala bicolor.
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.
AID1755200	Inhibition of PTP1B (unknown origin)	2021	Bioorganic & medicinal chemistry, 08-15, Volume: 44	Pyrrolo[1,2-a]quinoxal-5-inium salts and 4,5-dihydropyrrolo[1,2-a]quinoxalines: Synthesis, activity and computational docking for protein tyrosine phosphatase 1B.
AID1326307	Antibacterial activity against methicillin-resistant Staphylococcus aureus ATCC BAA-41 after 18 hrs by broth microdilution method	2016	Bioorganic & medicinal chemistry, 12-15, Volume: 24, Issue:24	Recent advances in the discovery and development of antibacterial agents targeting the cell-division protein FtsZ.
AID1764181	Hypolipidemic activity against oleic acid/palmitic acid-induced hyperlipidemia in human HepG2 cells assessed as reduction in triglycerides content	2021	Bioorganic & medicinal chemistry letters, 09-01, Volume: 47	Phenolic compounds from the leaves of Crataegus pinnatifida Bge. var. major N.E.Br. And their lipid-lowering effects.
AID1699042	Inhibition of quorum sensing system in Stenotrophomonas maltophilia	2020	Bioorganic & medicinal chemistry, 11-01, Volume: 28, Issue:21	Next generation quorum sensing inhibitors: Accounts on structure activity relationship studies and biological activities.
AID1176147	Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-stimulated TNFalpha production at 2 uM by ELISA	2015	Bioorganic & medicinal chemistry letters, Jan-15, Volume: 25, Issue:2	Anti-inflammatory components of Chrysanthemum indicum flowers.
AID688479	Inhibition of human amyloid beta (1 to 42) aggregation after 24 hrs by thioflavin-T fluorescence assay	2012	Bioorganic & medicinal chemistry, Oct-01, Volume: 20, Issue:19	Protective effects of caffeoylquinic acids on the aggregation and neurotoxicity of the 42-residue amyloid β-protein.
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.
AID1766075	Cytotoxicity against in mouse 3T3-L1 cells assessed as reduction in cell viability at 100 uM incubated for 24 hrs by MTT assay relative to control	2021	Bioorganic & medicinal chemistry letters, 10-01, Volume: 49	Phytochemicals from the flowers of Prunus persica (L.) Batsch: Anti-adipogenic effect of mandelamide on 3T3-L1 preadipocytes.
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.
AID104233	Lethal dose (LD5) concentration inhibiting growth of MT-2 cells by 5%	1999	Journal of medicinal chemistry, Feb-11, Volume: 42, Issue:3	Structure-activity relationships: analogues of the dicaffeoylquinic and dicaffeoyltartaric acids as potent inhibitors of human immunodeficiency virus type 1 integrase and replication.
AID1223493	Apparent permeability from apical to basolateral side in human Caco2 cells at 500 uM at pH 7.4 after 1 hr by HPLC-DAD analysis	2012	Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 40, Issue:2	Predicting phenolic acid absorption in Caco-2 cells: a theoretical permeability model and mechanistic study.
AID1223495	Efflux ratio of apparent permeability from basolateral to apical side over apical to basolateral side in human Caco2 cells at 500 uM after 1 hr by HPLC-DAD analysis	2012	Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 40, Issue:2	Predicting phenolic acid absorption in Caco-2 cells: a theoretical permeability model and mechanistic study.
AID1460719	Neuroprotective activity in human SH-SY5Y cells assessed as reduction in hydrogen peroxide-induced cytotoxicity by measuring cell viability level at 10 uM (Rvb = 50.7+/- 2.6%)	2017	Journal of natural products, 04-28, Volume: 80, Issue:4	Neuroprotective Caffeoylquinic Acid Derivatives from the Flowers of Chrysanthemum morifolium.
AID1056519	Cytotoxicity against human A549 cells at 10 uM after 96 hrs by MTT assay	2013	Journal of natural products, Dec-27, Volume: 76, Issue:12	Homosecoiridoid alkaloids with amino acid units from the flower buds of Lonicera japonica.
AID1223496	Apparent permeability across human Caco2 cells with high TEER resistance at 500 uM after 1 hr by HPLC-DAD analysis	2012	Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 40, Issue:2	Predicting phenolic acid absorption in Caco-2 cells: a theoretical permeability model and mechanistic study.
AID91578	Inhibition of Human Immunodeficiency Virus Type 1 integrase (HIV-1 IN) in the disintegration reaction at a concentration of 25 uM	1999	Journal of medicinal chemistry, Feb-11, Volume: 42, Issue:3	Structure-activity relationships: analogues of the dicaffeoylquinic and dicaffeoyltartaric acids as potent inhibitors of human immunodeficiency virus type 1 integrase and replication.
AID1374940	Inhibition of TCPTP (unknown origin)	2018	Bioorganic & medicinal chemistry letters, 04-15, Volume: 28, Issue:7	Identification of caffeoylquinic acid derivatives as natural protein tyrosine phosphatase 1B inhibitors from Artemisia princeps.
AID1420942	Antibacterial activity against Enterococcus faecalis	2018	European journal of medicinal chemistry, Oct-05, Volume: 158	Antibacterial and antioxidant activities for natural and synthetic dual-active compounds.
AID1256763	Inhibition of Mycobacterium tuberculosis MTCC 300 DAH7PS expressed in Escherichia coli BL21 (DE3) using 25 to 125 uM PEP/100 uM E4P as substrate by spectrophotometric analysis	2015	European journal of medicinal chemistry, Nov-13, Volume: 105	Inhibition of 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase from Mycobacterium tuberculosis: in silico screening and in vitro validation.
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.
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.
AID93700	Inhibitory concentration of compound against 3'-processing of HIV-1 integrase in experiment 1	1997	Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6	Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching.
AID378769	Immunomodulatory activity in phytochemagglutininin-stimulatedHMNC assessed as IFN-gamma production after 3 days by EIA	1999	Journal of natural products, Mar, Volume: 62, Issue:3	Immunomodulatory principles of Dichrocephala bicolor.
AID1326317	Antimicrobial activity against vancomycin-resistant Enterococcus faecalis after 18 hrs by broth microdilution method	2016	Bioorganic & medicinal chemistry, 12-15, Volume: 24, Issue:24	Recent advances in the discovery and development of antibacterial agents targeting the cell-division protein FtsZ.
AID91562	Percentage inhibition against strand transfer of HIV-1 integrase at 100 ug/mL	1997	Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6	Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching.
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.
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.
AID1374938	Selectivity index, ratio of inhibition of PTP1B (unknown origin) to inhibition of SHP1 (unknown origin)	2018	Bioorganic & medicinal chemistry letters, 04-15, Volume: 28, Issue:7	Identification of caffeoylquinic acid derivatives as natural protein tyrosine phosphatase 1B inhibitors from Artemisia princeps.
AID580006	Antiobesity activity against high-fat diet fed ICR mouse assessed as increase in basal metabolic rate at 0.1 % after 4 weeks	2011	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 21, Issue:6	Anti-obesity compounds in green leaves of Eucommia ulmoides.
AID91426	Tested for inhibition of HIV-1 integrase, under 1 uM for the strand transfer	2000	Journal of medicinal chemistry, Jun-01, Volume: 43, Issue:11	Developing a dynamic pharmacophore model for HIV-1 integrase.
AID419928	Inhibition of STAT1 SH2 domain at 200 uM	2009	Bioorganic & medicinal chemistry letters, Jun-15, Volume: 19, Issue:12	Natural product inhibitors of protein-protein interactions mediated by Src-family SH2 domains.
AID735121	Gastroprotective activity in rat assessed as protection against ethanol-induced gastric injury	2013	Journal of natural products, Mar-22, Volume: 76, Issue:3	Mexican antidiabetic herbs: valuable sources of inhibitors of α-glucosidases.
AID1223497	Apparent permeability across human Caco2 cells with low TEER resistance at 500 uM after 1 hr by HPLC-DAD analysis	2012	Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 40, Issue:2	Predicting phenolic acid absorption in Caco-2 cells: a theoretical permeability model and mechanistic study.
AID338035	Hepatoprotective activity against carbon tetrachloride-induced hepatotoxicity in fasted Sprague-Dawley rat hepatocytes assessed as serum glutamic pyruvate transaminase release at 0.1 mg/ml administered before 10 mins of carbon tetrachloride challenge meas
AID357272	Inhibition of A23187-induced LTB4 formation in human polymorphonuclear leukocytes
AID718319	Antioxidant activity assessed as trolox equivalents of ABTS radical scavenging activity at 30 mins by TEAC assay	2012	Journal of natural products, Dec-28, Volume: 75, Issue:12	Antioxidant glucosylated caffeoylquinic acid derivatives in the invasive tropical soda apple, Solanum viarum.
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.
AID447578	Inhibition of HDAC in human Hela cells nuclear extracts assessed as residual activity at 500 uM by fluorimetric assay	2009	Bioorganic & medicinal chemistry, Jul-15, Volume: 17, Issue:14	Molecular modifications on carboxylic acid derivatives as potent histone deacetylase inhibitors: Activity and docking studies.
AID1374936	Selectivity index, ratio of inhibition of PTP1B (unknown origin) to inhibition of TCPTP (unknown origin)	2018	Bioorganic & medicinal chemistry letters, 04-15, Volume: 28, Issue:7	Identification of caffeoylquinic acid derivatives as natural protein tyrosine phosphatase 1B inhibitors from Artemisia princeps.
AID379094	Stimulation of BALB/c mouse cloned 3T3/A31 cells growth at 0.01 to 0.1 ug/mL	1999	Journal of natural products, Mar, Volume: 62, Issue:3	Activities of plant-derived phenols in a fibroblast cell culture model
AID379094	Stimulation of BALB/c mouse cloned 3T3/A31 cells growth at 0.01 to 0.1 ug/mL	1999	Journal of natural products, Mar, Volume: 62, Issue:3	Activities of plant-derived phenols in a fibroblast cell culture model.
AID338032	Hepatoprotective activity against carbon tetrachloride-induced hepatotoxicity in fasted Sprague-Dawley rat hepatocytes assessed as serum glutamic oxaloacetic transaminase release at 1 mg/ml administered before 10 mins of carbon tetrachloride challenge mea
AID338037	Hepatoprotective activity against carbon tetrachloride-induced hepatotoxicity in fasted Sprague-Dawley rat hepatocytes assessed as serum glutamic pyruvate transaminase release at 3 mg/ml administered before 10 mins of carbon tetrachloride challenge measur
AID1705068	Inhibition of Influenza A virus (A/California/07/2009(H1N1)) neuraminidase at 400 uM by DNA-linked inhibitor antibody assay	2020	European journal of medicinal chemistry, Dec-15, Volume: 208	Unraveling the anti-influenza effect of flavonoids: Experimental validation of luteolin and its congeners as potent influenza endonuclease inhibitors.
AID1374929	Inhibition of PTP1B (unknown origin)	2018	Bioorganic & medicinal chemistry letters, 04-15, Volume: 28, Issue:7	Identification of caffeoylquinic acid derivatives as natural protein tyrosine phosphatase 1B inhibitors from Artemisia princeps.
AID580005	Antiobesity activity against high-fat diet fed ICR mouse assessed as decrease in plasma free fatty acid level after 4 weeks relative to high-fat diet fed group	2011	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 21, Issue:6	Anti-obesity compounds in green leaves of Eucommia ulmoides.
AID1420941	Antibacterial activity against Staphylococcus aureus	2018	European journal of medicinal chemistry, Oct-05, Volume: 158	Antibacterial and antioxidant activities for natural and synthetic dual-active compounds.
AID515790	Antifungal activity against Candida albicans by NCCLS method	2010	Bioorganic & medicinal chemistry, Oct-01, Volume: 18, Issue:19	Synthesis, anti-fungal and 1,3-β-D-glucan synthase inhibitory activities of caffeic and quinic acid derivatives.
AID356132	Antioxidant activity assessed as DPPH radical scavenging activity after 30 mins	2003	Journal of natural products, Jul, Volume: 66, Issue:7	Bioactive novel polyphenols from the fruit of Manilkara zapota (Sapodilla).
AID338034	Hepatoprotective activity against carbon tetrachloride-induced hepatotoxicity in fasted Sprague-Dawley rat hepatocytes assessed as serum glutamic pyruvate transaminase release at 0.01 mg/ml administered before 10 mins of carbon tetrachloride challenge mea
AID654332	Inhibition of advanced glycation end-products formation after 14 days by spectrofluorimetry	2012	Journal of natural products, Feb-24, Volume: 75, Issue:2	Chemical constituents from the aerial parts of Aster koraiensis with protein glycation and aldose reductase inhibitory activities.
AID736009	Antioxidant activity assessed as DPPH radical scavenging activity after 30 mins by microplate reader	2013	Journal of natural products, Feb-22, Volume: 76, Issue:2	Flavone tetraglycosides and benzyl alcohol glycosides from the Mongolian medicinal plant Dracocephalum ruyschiana.
AID1256312	Increase in glucose-stimulated insulin secretion in rat INS-1E cells at 1 uM after 60 mins in presence of 16.7 mM glucose	2015	Journal of natural products, Oct-23, Volume: 78, Issue:10	Cafestol, a Bioactive Substance in Coffee, Stimulates Insulin Secretion and Increases Glucose Uptake in Muscle Cells: Studies in Vitro.
AID309262	Antifungal activity against Candida albicans ATCC 90028 after 18 to 24 hrs	2007	Bioorganic & medicinal chemistry, Nov-01, Volume: 15, Issue:21	Synthesis of chlorogenic acid derivatives with promising antifungal activity.
AID718321	Antioxidant activity assessed as trolox equivalents of ABTS radical scavenging activity at 25 mins by TEAC assay	2012	Journal of natural products, Dec-28, Volume: 75, Issue:12	Antioxidant glucosylated caffeoylquinic acid derivatives in the invasive tropical soda apple, Solanum viarum.
AID420055	Inhibition of STAT5b SH2 domain at 200 uM	2009	Bioorganic & medicinal chemistry letters, Jun-15, Volume: 19, Issue:12	Natural product inhibitors of protein-protein interactions mediated by Src-family SH2 domains.
AID1326318	Antimicrobial activity against vancomycin-sensitive Enterococcus faecalis after 18 hrs by broth microdilution method	2016	Bioorganic & medicinal chemistry, 12-15, Volume: 24, Issue:24	Recent advances in the discovery and development of antibacterial agents targeting the cell-division protein FtsZ.
AID378768	Immunomodulatory activity in phytochemagglutininin-stimulatedHMNC assessed as IFN-gamma production at 10 ug/mL after 3 days by EIA realtive to control	1999	Journal of natural products, Mar, Volume: 62, Issue:3	Immunomodulatory principles of Dichrocephala bicolor.
AID419927	Inhibition of SRC SH2 domain at 200 uM	2009	Bioorganic & medicinal chemistry letters, Jun-15, Volume: 19, Issue:12	Natural product inhibitors of protein-protein interactions mediated by Src-family SH2 domains.
AID1326306	Antibacterial activity against Escherichia coli ATCC 25922 after 18 hrs by broth microdilution method	2016	Bioorganic & medicinal chemistry, 12-15, Volume: 24, Issue:24	Recent advances in the discovery and development of antibacterial agents targeting the cell-division protein FtsZ.
AID93705	Inhibitory concentration of compound against strand transfer of HIV-1 integrase in experiment 1	1997	Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6	Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching.
AID1265118	Inhibition of recombinant human N-terminal His6-tagged AKR1B10 expressed in Escherichia coli BL21 cells using all-trans-retinal as substrate at 20 uM incubated for 15 mins by HPLC method	2015	Journal of natural products, Nov-25, Volume: 78, Issue:11	Flavones Inhibit the Activity of AKR1B10, a Promising Therapeutic Target for Cancer Treatment.
AID780479	Antimicrobial activity against Pseudomonas aeruginosa PaM02 at > 128 ug/ml by microtitre plate reader analysis	2013	Bioorganic & medicinal chemistry, Nov-15, Volume: 21, Issue:22	Spectroscopic identification and anti-biofilm properties of polar metabolites from the medicinal plant Helichrysum italicum against Pseudomonas aeruginosa.
AID447579	Inhibition of HDAC in human Hela cells nuclear extracts by fluorimetric assay	2009	Bioorganic & medicinal chemistry, Jul-15, Volume: 17, Issue:14	Molecular modifications on carboxylic acid derivatives as potent histone deacetylase inhibitors: Activity and docking studies.
AID391607	Inhibition of Bacillus stearothermophilus alpha-glucosidase	2008	Journal of medicinal chemistry, Oct-09, Volume: 51, Issue:19	Chlorogenic acid derivatives with alkyl chains of different lengths and orientations: potent alpha-glucosidase inhibitors.
AID294174	Inhibition of diphenolase activity of mushroom tyrosinase at 0.049 mM	2007	Bioorganic & medicinal chemistry, Apr-01, Volume: 15, Issue:7	Identification of tyrosinase inhibitors from Marrubium velutinum and Marrubium cylleneum.
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.
AID311351	Inhibition of Cu2+ induced human LDL oxidation	2007	Journal of natural products, Sep, Volume: 70, Issue:9	Targeted natural product isolation guided by HPLC-SPE-NMR: constituents of Hubertia species.
AID624612	Specific activity of expressed human recombinant UGT1A9	2000	Annual review of pharmacology and toxicology, , Volume: 40	Human UDP-glucuronosyltransferases: metabolism, expression, and disease.
AID378765	Induction of phytohemagglutininin-activated HMNC proliferation assessed as [3H]thymidine uptake after 3 days by lymphoproliferation test	1999	Journal of natural products, Mar, Volume: 62, Issue:3	Immunomodulatory principles of Dichrocephala bicolor.
AID311973	Hepatoprotective activity against HBV in human HepG2.2.15 cells	2007	Bioorganic & medicinal chemistry letters, Dec-15, Volume: 17, Issue:24	Isolation of quinic acid derivatives and flavonoids from the aerial parts of Lactuca indica L. and their hepatoprotective activity in vitro.
AID1293874	Inhibition of HDAC in human HeLa nuclear extract using fluor de lys as substrate after 10 to 15 mins by spectrofluorometry	2016	Bioorganic & medicinal chemistry letters, May-01, Volume: 26, Issue:9	Identification of new quinic acid derivatives as histone deacetylase inhibitors by fluorescence-based cellular assay.
AID1374933	Inhibition of VHR (unknown origin) at 100 uM relative to control	2018	Bioorganic & medicinal chemistry letters, 04-15, Volume: 28, Issue:7	Identification of caffeoylquinic acid derivatives as natural protein tyrosine phosphatase 1B inhibitors from Artemisia princeps.
AID106907	Concentration that inhibits Human Immunodeficiency Virus Type 1 (HIV-1)-induced death of MT-2 cells	1999	Journal of medicinal chemistry, Feb-11, Volume: 42, Issue:3	Structure-activity relationships: analogues of the dicaffeoylquinic and dicaffeoyltartaric acids as potent inhibitors of human immunodeficiency virus type 1 integrase and replication.
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.
AID465832	Hepatoprotective activity in rat WB-F344 cells assessed as inhibition of D-galactosamine-induced cytotoxicity at 10 uM after 1 hrs by MTT assay relative to control treated before D-galactosamine challenge	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	Hepatoprotective constituents from the roots and stems of Erycibe hainanesis.
AID379089	Growth inhibition of BALB/c mouse cloned 3T3/A31 cells after 72 hrs by nigrosin assay	1999	Journal of natural products, Mar, Volume: 62, Issue:3	Activities of plant-derived phenols in a fibroblast cell culture model
AID379089	Growth inhibition of BALB/c mouse cloned 3T3/A31 cells after 72 hrs by nigrosin assay	1999	Journal of natural products, Mar, Volume: 62, Issue:3	Activities of plant-derived phenols in a fibroblast cell culture model.
AID1374939	Selectivity index, ratio of inhibition of PTP1B (unknown origin) to inhibition of SHP2 (unknown origin)	2018	Bioorganic & medicinal chemistry letters, 04-15, Volume: 28, Issue:7	Identification of caffeoylquinic acid derivatives as natural protein tyrosine phosphatase 1B inhibitors from Artemisia princeps.
AID357273	Inhibition of A23187-induced 12-hydroxy-5,8,10-heptadecatrienoic acid formation in human polymorphonuclear leukocytes
AID449328	Antioxidant activity assessed as DPPH radical scavenging activity by UV-visible spectrophotometry	2009	Bioorganic & medicinal chemistry letters, Sep-15, Volume: 19, Issue:18	Synthesis and biological evaluation of quinic acid derivatives as anti-inflammatory agents.
AID718318	Antioxidant activity assessed as trolox equivalents of ABTS radical scavenging activity at 40 mins by TEAC assay	2012	Journal of natural products, Dec-28, Volume: 75, Issue:12	Antioxidant glucosylated caffeoylquinic acid derivatives in the invasive tropical soda apple, Solanum viarum.
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.
AID289011	Antioxidant activity assessed as DPPH radical scavenging activity	2007	Journal of natural products, Jun, Volume: 70, Issue:6	Biologically active natural products from Mongolian medicinal plants Scorzonera divaricata and Scorzonera pseudodivaricata.
AID1293873	Inhibition of HDAC in mouse C127-LT cells assessed as activation of EGFP expression at 10 uM after 24 hrs by fluorescence microscopy	2016	Bioorganic & medicinal chemistry letters, May-01, Volume: 26, Issue:9	Identification of new quinic acid derivatives as histone deacetylase inhibitors by fluorescence-based cellular assay.
AID1326320	Antibacterial activity against methicillin-sensitive Staphylococcus aureus after 18 hrs by broth microdilution method	2016	Bioorganic & medicinal chemistry, 12-15, Volume: 24, Issue:24	Recent advances in the discovery and development of antibacterial agents targeting the cell-division protein FtsZ.
AID356134	Cytotoxicity against human SW480 cells after 72 hrs by MTT assay	2003	Journal of natural products, Jul, Volume: 66, Issue:7	Bioactive novel polyphenols from the fruit of Manilkara zapota (Sapodilla).
AID309266	Lethality in brine shrimp at 100 ug/ml	2007	Bioorganic & medicinal chemistry, Nov-01, Volume: 15, Issue:21	Synthesis of chlorogenic acid derivatives with promising antifungal activity.
AID1223494	Apparent permeability from basolateral to apical side in human Caco2 cells at 500 uM at pH 7.4 after 1 hr by HPLC-DAD analysis	2012	Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 40, Issue:2	Predicting phenolic acid absorption in Caco-2 cells: a theoretical permeability model and mechanistic study.
AID93702	Inhibitory concentration of compound against 3'-processing of HIV-1 integrase in experiment 2	1997	Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6	Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching.
AID718322	Antioxidant activity assessed as trolox equivalents of ABTS radical scavenging activity at 20 mins by TEAC assay	2012	Journal of natural products, Dec-28, Volume: 75, Issue:12	Antioxidant glucosylated caffeoylquinic acid derivatives in the invasive tropical soda apple, Solanum viarum.
AID420054	Inhibition of STAT3 SH2 domain at 200 uM	2009	Bioorganic & medicinal chemistry letters, Jun-15, Volume: 19, Issue:12	Natural product inhibitors of protein-protein interactions mediated by Src-family SH2 domains.
AID780477	Inhibition of biofilm formation of Pseudomonas aeruginosa PaM02 at 128 ug/ml after 24 hrs by crystal violet staining-based ELISA reader analysis	2013	Bioorganic & medicinal chemistry, Nov-15, Volume: 21, Issue:22	Spectroscopic identification and anti-biofilm properties of polar metabolites from the medicinal plant Helichrysum italicum against Pseudomonas aeruginosa.
AID697853	Inhibition of horse BChE at 2 mg/ml by Ellman's method	2012	Bioorganic & medicinal chemistry, Nov-15, Volume: 20, Issue:22	Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.
AID1326311	Inhibition of Escherichia coli FtsZ polymerization expressed in Escherichia coli BL21 assessed as reduction in light scattering intensity in presence of GTP by fluorescence spectrometric analysis	2016	Bioorganic & medicinal chemistry, 12-15, Volume: 24, Issue:24	Recent advances in the discovery and development of antibacterial agents targeting the cell-division protein FtsZ.
AID580001	Antiobesity activity against high-fat diet fed ICR mouse assessed as change in body weight after 4 weeks (high fat diet fed group = 9.50 +/- 0.68 g)	2011	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 21, Issue:6	Anti-obesity compounds in green leaves of Eucommia ulmoides.
AID355885	Antimicrobial activity against Helicobacter pylori isolates after 36 hrs under aerobic condition by microdilution method	2003	Journal of natural products, May, Volume: 66, Issue:5	Sesquiterpene lactones from Anthemis altissima and their anti-Helicobacter pylori activity.
AID338031	Hepatoprotective activity against carbon tetrachloride-induced hepatotoxicity in fasted Sprague-Dawley rat hepatocytes assessed as serum glutamic oxaloacetic transaminase release at 0.1 mg/ml administered before 10 mins of carbon tetrachloride challenge m
AID1424235	Antioxidant activity assessed as alkoxyl radical scavenging activity by measuring rate constant by ESR spin trapping method	2017	European journal of medicinal chemistry, Jun-16, Volume: 133	Free radicals and polyphenols: The redox chemistry of neurodegenerative diseases.
AID357275	Inhibition of A23187-induced 15HETE formation in human polymorphonuclear leukocytes
AID580004	Antiobesity activity against high-fat diet fed ICR mouse assessed as decrease in plasma triglyceride level after 4 weeks relative to high-fat diet fed group	2011	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 21, Issue:6	Anti-obesity compounds in green leaves of Eucommia ulmoides.
AID592361	Antioxidant activity assessed as DPPH free radical scavenging activity after 30 mins in dark by spectrophotometry	2011	Journal of natural products, Mar-25, Volume: 74, Issue:3	An unprecedented neolignan skeleton from Chimarrhis turbinata.
AID1176142	Cytotoxicity against mouse RAW264.7 cells at 50 uM by MTT assay	2015	Bioorganic & medicinal chemistry letters, Jan-15, Volume: 25, Issue:2	Anti-inflammatory components of Chrysanthemum indicum flowers.
AID1179732	Antioxidant activity assessed as superoxide anion radical scavenging activity at 10 uM by PMS-NADH-NBT system based spectrophotometry	2014	Bioorganic & medicinal chemistry, Aug-01, Volume: 22, Issue:15	Synthesis, antioxidant and cytoprotective evaluation of potential antiatherogenic phenolic hydrazones. A structure-activity relationship insight.
AID93707	Inhibitory concentration of compound against strand transfer of HIV-1 integrase in experiment 2	1997	Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6	Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching.
AID697852	Inhibition of electric eel AChE at 2 mg/ml by Ellman's method	2012	Bioorganic & medicinal chemistry, Nov-15, Volume: 20, Issue:22	Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.
AID1569194	Osteo-blastogenic activity in mouse MC3T3-E1 cells assessed as stimulation of ALP activity at 10 uM supplemented with fresh medium every 3 to 4 days and measured after 14 days relative to control
AID378764	Induction of phytohemagglutininin-activated HMNC proliferation assessed as [3H]thymidine uptake at 10 ug/mL after 3 days by lymphoproliferation test relative to control	1999	Journal of natural products, Mar, Volume: 62, Issue:3	Immunomodulatory principles of Dichrocephala bicolor.
AID1056518	Cytotoxicity against human BGC823 cells at 10 uM after 96 hrs by MTT assay	2013	Journal of natural products, Dec-27, Volume: 76, Issue:12	Homosecoiridoid alkaloids with amino acid units from the flower buds of Lonicera japonica.
AID338030	Hepatoprotective activity against carbon tetrachloride-induced hepatotoxicity in fasted Sprague-Dawley rat hepatocytes assessed as serum glutamic oxaloacetic transaminase release at 0.01 mg/ml administered before 10 mins of carbon tetrachloride challenge
AID1193989	Inhibition of LPS-induced IL-6 production in wild-type C57BL/6 mouse BMDC pretreated with compound for 1 hr before LPS treatment measured 16 hrs by ELISA	2015	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7	Chemical constituents from Kandelia candel with their inhibitory effects on pro-inflammatory cytokines production in LPS-stimulated bone marrow-derived dendritic cells (BMDCs).
AID1293875	Inhibition of HDAC in human HeLa cells using Boc-Lys(AC)-AMC as substrate after 24 to 48 hrs by spectrofluorometry	2016	Bioorganic & medicinal chemistry letters, May-01, Volume: 26, Issue:9	Identification of new quinic acid derivatives as histone deacetylase inhibitors by fluorescence-based cellular assay.
AID338033	Hepatoprotective activity against carbon tetrachloride-induced hepatotoxicity in fasted Sprague-Dawley rat hepatocytes assessed as serum glutamic oxaloacetic transaminase release at 3 mg/ml administered before 10 mins of carbon tetrachloride challenge mea
AID515789	Inhibition of Candida albicans 1,3 beta-D-glucan synthase	2010	Bioorganic & medicinal chemistry, Oct-01, Volume: 18, Issue:19	Synthesis, anti-fungal and 1,3-β-D-glucan synthase inhibitory activities of caffeic and quinic acid derivatives.
AID1256761	Inhibition of Mycobacterium tuberculosis MTCC 300 DAH7PS expressed in Escherichia coli BL21 (DE3) using 25 to 125 uM PEP/100 uM E4P as substrate up to 50 nM by spectrophotometric analysis	2015	European journal of medicinal chemistry, Nov-13, Volume: 105	Inhibition of 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase from Mycobacterium tuberculosis: in silico screening and in vitro validation.
AID1223489	1-Octanol-water distribution coefficient, log D of the compound at pH 7.4 by shake flask method	2012	Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 40, Issue:2	Predicting phenolic acid absorption in Caco-2 cells: a theoretical permeability model and mechanistic study.
AID1056514	Cytotoxicity against human HCT8 cells at 10 uM after 96 hrs by MTT assay	2013	Journal of natural products, Dec-27, Volume: 76, Issue:12	Homosecoiridoid alkaloids with amino acid units from the flower buds of Lonicera japonica.
AID355888	Antimicrobial activity against Pseudomonas aeruginosa ATCC 27853 after 36 hrs under aerobic condition by microdilution method	2003	Journal of natural products, May, Volume: 66, Issue:5	Sesquiterpene lactones from Anthemis altissima and their anti-Helicobacter pylori activity.
AID580000	Antiobesity activity against high-fat diet fed ICR mouse assessed as change in final body weight after 4 weeks (high fat diet fed group = 35.5 +/- 0.68 g)	2011	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 21, Issue:6	Anti-obesity compounds in green leaves of Eucommia ulmoides.
AID1176144	Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-stimulated nitric oxide production at 0.4 to 10 uM after 24 hrs by Griess assay	2015	Bioorganic & medicinal chemistry letters, Jan-15, Volume: 25, Issue:2	Anti-inflammatory components of Chrysanthemum indicum flowers.
AID1193990	Inhibition of LPS-induced TNF-alpha production in wild-type C57BL/6 mouse BMDC pretreated with compound for 1 hr before LPS treatment measured 16 hrs by ELISA	2015	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7	Chemical constituents from Kandelia candel with their inhibitory effects on pro-inflammatory cytokines production in LPS-stimulated bone marrow-derived dendritic cells (BMDCs).
AID1056516	Cytotoxicity against human Bel7402 cells at 10 uM after 96 hrs by MTT assay	2013	Journal of natural products, Dec-27, Volume: 76, Issue:12	Homosecoiridoid alkaloids with amino acid units from the flower buds of Lonicera japonica.
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.
AID1272817	Antioxidative activity of the compound assessed as DPPH radical scavenging activity	2016	Bioorganic & medicinal chemistry letters, Feb-01, Volume: 26, Issue:3	Alkenes with antioxidative activities from Murraya koenigii (L.) Spreng.
AID654333	Inhibition of Sprague-Dawley rat lens aldose reductase	2012	Journal of natural products, Feb-24, Volume: 75, Issue:2	Chemical constituents from the aerial parts of Aster koraiensis with protein glycation and aldose reductase inhibitory activities.
AID357274	Inhibition of A23187-induced 5HETE formation in human polymorphonuclear leukocytes
AID579999	Antiobesity activity against high-fat diet fed ICR mouse assessed as change in initial body weight after 4 weeks (high fat diet fed group = 25.9 +/- 0.38 g)	2011	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 21, Issue:6	Anti-obesity compounds in green leaves of Eucommia ulmoides.
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.
AID641085	Inhibition of human recombinant N-terminus His6-tagged AKR1B1 expressed in Escherichia coli BL21 DE3 assessed as pyridine-3-aldehyde reduction by spectrometric analysis	2012	European journal of medicinal chemistry, Feb, Volume: 48	Design, synthesis and evaluation of caffeic acid phenethyl ester-based inhibitors targeting a selectivity pocket in the active site of human aldo-keto reductase 1B10.
AID1176146	Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-stimulated TNFalpha production at 10 uM by ELISA	2015	Bioorganic & medicinal chemistry letters, Jan-15, Volume: 25, Issue:2	Anti-inflammatory components of Chrysanthemum indicum flowers.
AID309265	Antifungal activity against Candida krusei ATCC 6258	2007	Bioorganic & medicinal chemistry, Nov-01, Volume: 15, Issue:21	Synthesis of chlorogenic acid derivatives with promising antifungal activity.
AID311974	Antiviral activity against hepatitis B virus assessed as inhibition of viral particle production	2007	Bioorganic & medicinal chemistry letters, Dec-15, Volume: 17, Issue:24	Isolation of quinic acid derivatives and flavonoids from the aerial parts of Lactuca indica L. and their hepatoprotective activity in vitro.
AID1169291	Inhibition of TTR V30M mutant (unknown origin) expressed in Escherichia coli assessed as inhibition of amyloid fibril formation by fluorescence assay	2014	Journal of medicinal chemistry, Nov-13, Volume: 57, Issue:21	Inhibitory activities of propolis and its promising component, caffeic acid phenethyl ester, against amyloidogenesis of human transthyretin.
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.
AID397154	Antioxidant activity against AAPH-induced lipid peroxidation in human plasma LDL 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.
AID718324	Antioxidant activity assessed as trolox equivalents of ABTS radical scavenging activity at 5 mins by TEAC assay	2012	Journal of natural products, Dec-28, Volume: 75, Issue:12	Antioxidant glucosylated caffeoylquinic acid derivatives in the invasive tropical soda apple, Solanum viarum.
AID391608	Inhibition of Saccharomyces cerevisiae alpha-glucosidase	2008	Journal of medicinal chemistry, Oct-09, Volume: 51, Issue:19	Chlorogenic acid derivatives with alkyl chains of different lengths and orientations: potent alpha-glucosidase inhibitors.
AID639825	Inhibition of human recombinant aldose reductase using D-glyceraldehyde as substrate preincubated for 10 mins before substrate addition measured for every 10 secs for 50 mins by spectrophotometry	2012	Bioorganic & medicinal chemistry, Feb-01, Volume: 20, Issue:3	Construction of an Indonesian herbal constituents database and its use in Random Forest modelling in a search for inhibitors of aldose reductase.
AID1056515	Cytotoxicity against human Ketr3 cells at 10 uM after 96 hrs by MTT assay	2013	Journal of natural products, Dec-27, Volume: 76, Issue:12	Homosecoiridoid alkaloids with amino acid units from the flower buds of Lonicera japonica.
AID356133	Cytotoxicity against human HCT116 cells after 72 hrs by MTT assay	2003	Journal of natural products, Jul, Volume: 66, Issue:7	Bioactive novel polyphenols from the fruit of Manilkara zapota (Sapodilla).
AID75271	Inhibition glucose-6-phosphate hydrolysis in highly intact microsomal preparations obtained from livers of 20-h fasted rats.	1997	Journal of medicinal chemistry, Jan-17, Volume: 40, Issue:2	Chlorogenic acid and synthetic chlorogenic acid derivatives: novel inhibitors of hepatic glucose-6-phosphate translocase.
AID1327604	Inhibition of hog pancreas alpha-amylase using starch as substrate preincubated for 10 mins followed by substrate addition measured after 10 mins by dinitrosalicylic acid color reagent-based UV-Vis spectrophotometric analysis	2016	Journal of natural products, 08-26, Volume: 79, Issue:8	α-Glucosidase and α-Amylase Inhibitors from Arcytophyllum thymifolium.
AID355887	Antimicrobial activity against Proteus mirabilis isolates after 36 hrs under aerobic condition by microdilution method	2003	Journal of natural products, May, Volume: 66, Issue:5	Sesquiterpene lactones from Anthemis altissima and their anti-Helicobacter pylori activity.
AID1056513	Antiviral activity against HIV1 infected in human 293T cells expressing VSV-G assessed as inhibition of viral p24 production at 10 uM after 48 hrs by ELISA	2013	Journal of natural products, Dec-27, Volume: 76, Issue:12	Homosecoiridoid alkaloids with amino acid units from the flower buds of Lonicera japonica.
AID1424233	Antioxidant activity assessed as hydroxyl radical scavenging activity by measuring rate constant using UV irradiation by ESR spin trapping method	2017	European journal of medicinal chemistry, Jun-16, Volume: 133	Free radicals and polyphenols: The redox chemistry of neurodegenerative diseases.
AID592088	Antihemorrhagic activity in ddY mouse assessed as inhibition of Protobothrops flavoviridis venom-induced hemorrhage incubated with compound for 10 mins measured after 24 hrs	2011	Bioorganic & medicinal chemistry, Apr-01, Volume: 19, Issue:7	Contribution of cinnamic acid analogues in rosmarinic acid to inhibition of snake venom induced hemorrhage.
AID1056517	Cytotoxicity against human MCF7 cells at 10 uM after 96 hrs by MTT assay	2013	Journal of natural products, Dec-27, Volume: 76, Issue:12	Homosecoiridoid alkaloids with amino acid units from the flower buds of Lonicera japonica.
AID1460717	Neuroprotective activity in human SH-SY5Y cells assessed as reduction in oxygen-glucose deprivation-induced cytotoxicity at 10 uM relative to untreated control	2017	Journal of natural products, 04-28, Volume: 80, Issue:4	Neuroprotective Caffeoylquinic Acid Derivatives from the Flowers of Chrysanthemum morifolium.
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.
AID1696517	Antioxidant activity in pH 6.6 phosphate buffer assessed as increase in ferric ion-reducing activity at 1 mg/ml incubated for 20 mins followed by FeCl3 addition and measured after 30 mins by FRAP assay	2020	Bioorganic & medicinal chemistry letters, 11-01, Volume: 30, Issue:21	Isolation, reactivity, pharmacological activities and total synthesis of hispanolone and structurally related diterpenes from Labiatae plants.
AID1424234	Antioxidant activity assessed as singlet oxygen scavenging activity by measuring rate constant using VIS irradiation by ESR spin trapping method	2017	European journal of medicinal chemistry, Jun-16, Volume: 133	Free radicals and polyphenols: The redox chemistry of neurodegenerative diseases.
AID641086	Inhibition of human recombinant N-terminus His6-tagged AKR1B10 expressed in Escherichia coli BL21 DE3 assessed as pyridine-3-aldehyde reduction by spectrometric analysis	2012	European journal of medicinal chemistry, Feb, Volume: 48	Design, synthesis and evaluation of caffeic acid phenethyl ester-based inhibitors targeting a selectivity pocket in the active site of human aldo-keto reductase 1B10.
AID1424232	Antioxidant activity assessed as superoxide anion free radical scavenging activity by measuring rate constant using UV irradiation by ESR spin trapping method	2017	European journal of medicinal chemistry, Jun-16, Volume: 133	Free radicals and polyphenols: The redox chemistry of neurodegenerative diseases.
AID1546538	Antioxidant activity assessed as ONOO scavenging activity	2020	Bioorganic & medicinal chemistry, 01-01, Volume: 28, Issue:1	Artemisia: a promising plant for the treatment of cancer.
AID492140	Antioxidant activity assessed as formazan formation induced absorbance changes at 25 ppm at 570 nm at 37 degC for 6 hrs by MTT assay	2010	Journal of natural products, Jul-23, Volume: 73, Issue:7	An efficient and economical MTT assay for determining the antioxidant activity of plant natural product extracts and pure compounds.
AID357288	Cytotoxicity against human polymorphonuclear leukocytes assessed as occurrence of cell suspension or lactate dehydrogenase release at 1 to 1000 uM
AID1569195	Osteo-blastogenic activity in mouse MC3T3-E1 cells assessed as stimulation of ALP activity at 50 uM supplemented with fresh medium every 3 to 4 days and measured after 14 days relative to control
AID419926	Inhibition of LCK SH2 domain at 200 uM	2009	Bioorganic & medicinal chemistry letters, Jun-15, Volume: 19, Issue:12	Natural product inhibitors of protein-protein interactions mediated by Src-family SH2 domains.
AID378763	Induction of resting HMNC proliferation assessed as [3H]thymidine uptake at 10 ug/mL after 3 days by lymphoproliferation test relative to control	1999	Journal of natural products, Mar, Volume: 62, Issue:3	Immunomodulatory principles of Dichrocephala bicolor.
AID357283	Enhancement of PGE2 formation in A-23187-stimulated human polymorphonuclear leukocytes at 100 uM
AID1172640	Inhibition of cell proliferation of rat C6 cells assessed as cell viability at 100 uM after 72 hrs by sulforhodamine B assay	2014	Bioorganic & medicinal chemistry letters, Nov-15, Volume: 24, Issue:22	Bioactive triterpenoid saponins and phenolic compounds against glioma cells.
AID338036	Hepatoprotective activity against carbon tetrachloride-induced hepatotoxicity in fasted Sprague-Dawley rat hepatocytes assessed as serum glutamate pyruvate transaminase release at 1 mg/ml administered before 10 mins of carbon tetrachloride challenge measu
AID718455	Antioxidant activity assessed as trolox equivalents of ABTS radical scavenging activity at 0 min by TEAC assay	2012	Journal of natural products, Dec-28, Volume: 75, Issue:12	Antioxidant glucosylated caffeoylquinic acid derivatives in the invasive tropical soda apple, Solanum viarum.
AID1151279	Inhibition of BacLight Green labeled Escherichia coli adherence to human UEC after 1 hr by flow cytometry analysis	2014	Journal of natural products, May-23, Volume: 77, Issue:5	Development of a fluorometric microplate antiadhesion assay using uropathogenic Escherichia coli and human uroepithelial cells.
AID1193988	Inhibition of LPS-induced IL-12 p40 production in wild-type C57BL/6 mouse BMDC pretreated with compound for 1 hr before LPS treatment measured 16 hrs by ELISA	2015	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7	Chemical constituents from Kandelia candel with their inhibitory effects on pro-inflammatory cytokines production in LPS-stimulated bone marrow-derived dendritic cells (BMDCs).
AID580003	Antiobesity activity against high-fat diet fed ICR mouse assessed as decrease in weight adipose tissue weight after 4 weeks relative to high-fat diet fed group	2011	Bioorganic & medicinal chemistry letters, Mar-15, Volume: 21, Issue:6	Anti-obesity compounds in green leaves of Eucommia ulmoides.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745845	Primary qHTS for Inhibitors of ATXN expression
AID651635	Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID504812	Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign	2010	Endocrinology, Jul, Volume: 151, Issue:7	A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504810	Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign	2010	Endocrinology, Jul, Volume: 151, Issue:7	A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
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.
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.
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.
AID1805801	Various Assay from Article 10.1021/acs.jmedchem.1c00409: \\Perspectives on SARS-CoV-2 Main Protease Inhibitors.\\	2021	Journal of medicinal chemistry, 12-09, Volume: 64, Issue:23	Perspectives on SARS-CoV-2 Main Protease Inhibitors.
AID1802328	NMR Chemical Shift Titration Assay from Article 10.1021/acs.biochem.6b01025: \\Characterization of Protein Tyrosine Phosphatase 1B Inhibition by Chlorogenic Acid and Cichoric Acid.\\	2017	Biochemistry, Jan-10, Volume: 56, Issue:1	Characterization of Protein Tyrosine Phosphatase 1B Inhibition by Chlorogenic Acid and Cichoric Acid.
AID1802327	PTP1B Inhibition Assay from Article 10.1021/acs.biochem.6b01025: \\Characterization of Protein Tyrosine Phosphatase 1B Inhibition by Chlorogenic Acid and Cichoric Acid.\\	2017	Biochemistry, Jan-10, Volume: 56, Issue:1	Characterization of Protein Tyrosine Phosphatase 1B Inhibition by Chlorogenic Acid and Cichoric Acid.
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	176 (5.51)	18.7374
1990's	91 (2.85)	18.2507
2000's	564 (17.66)	29.6817
2010's	1609 (50.38)	24.3611
2020's	754 (23.61)	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	76 (2.32%)	5.53%
Reviews	110 (3.36%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	1 (0.03%)	0.25%
Other	3,089 (94.29%)	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
dinitrochlorobenzene Dinitrochlorobenzene: A skin irritant that may cause dermatitis of both primary and allergic types. Contact sensitization with DNCB has been used as a measure of cellular immunity. DNCB is also used as a reagent for the detection and determination of pyridine compounds.. 1-chloro-2,4-dinitrobenzene : A C-nitro compound that is chlorobenzene carrying a nitro substituent at each of the 2- and 4-positions.	1.96	1	0	C-nitro compound; monochlorobenzenes	allergen; epitope; sensitiser
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.	2.05	1	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.	8.36	50	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
3-hydroxyanthranilic acid 3-Hydroxyanthranilic Acid: An oxidation product of tryptophan metabolism. It may be a free radical scavenger and a carcinogen.. 3-hydroxyanthranilic acid : An aminobenzoic acid that is benzoic acid substituted at C-2 by an amine group and at C-3 by a hydroxy group. It is an intermediate in the metabolism of the amino acid tryptophan.. 3-hydroxyanthranilate : A hydroxybenzoate that is the conjugate base of 3-hydroxyanthranilic acid.	2.05	1	0	aminobenzoic acid; monohydroxybenzoic acid	human metabolite; mouse 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.	2.47	2	0	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.	2.54	2	0	benzenes; monocarboxylic acid	antifungal agent; human metabolite; plant metabolite
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.	3.21	5	0	amino acid zwitterion; gamma-amino acid; monocarboxylic acid	human metabolite; neurotransmitter; Saccharomyces cerevisiae metabolite; signalling molecule
4-hydroxybenzaldehyde [no description available]	2.08	1	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.	2.1	1	0	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.	5.48	11	0	monohydroxybenzoic acid	algal metabolite; plant metabolite
5-hydroxytryptophan 5-Hydroxytryptophan: The immediate precursor in the biosynthesis of SEROTONIN from tryptophan. It is used as an antiepileptic and antidepressant.. 5-hydroxytryptophan : A tryptophan derivative that is tryptophan substituted by a hydroxy group at position 5.	2.15	1	0	hydroxytryptophan	human metabolite; neurotransmitter
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.	7.58	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.	3.79	10	0	monocarboxylic acid	antimicrobial food preservative; Daphnia magna metabolite; food acidity regulator; protic solvent
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	2.76	2	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]	2.76	3	0	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
ammonium hydroxide azane : Saturated acyclic nitrogen hydrides having the general formula NnHn+2.	2.69	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.	2.05	1	0	aminobenzoic acid	human metabolite; mouse metabolite
beta-alanine [no description available]	2.1	1	0	amino acid zwitterion; beta-amino acid	agonist; fundamental metabolite; human metabolite; inhibitor; neurotransmitter
benzene [no description available]	5.19	3	1	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.	4.87	10	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.	3.1	1	0	benzyl alcohols	antioxidant; fragrance; metabolite; solvent
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)	2.52	2	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.	2.79	3	0	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.	3.82	3	0	fatty acid 4:0; straight-chain saturated fatty acid	human urinary metabolite; Mycoplasma genitalium metabolite
carbamates [no description available]	2.85	4	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.	1.97	1	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.	2.52	2	0	monocarboxylic acid	antibacterial agent; astringent; metabolite; protic solvent; solvent
aminooxyacetic acid Aminooxyacetic Acid: A compound that inhibits aminobutyrate aminotransferase activity in vivo, thereby raising the level of gamma-aminobutyric acid in tissues.. (aminooxy)acetic acid : A member of the class of hydroxylamines that is acetic acid substituted at postion 2 by an aminooxy group. It is a compound which inhibits aminobutyrate aminotransferase activity in vivo, resulting in increased levels of gamma-aminobutyric acid in tissues.	2.01	1	0	amino acid; hydroxylamines; monocarboxylic acid	anticonvulsant; EC 2.6.1.19 (4-aminobutyrate--2-oxoglutarate transaminase) inhibitor; EC 4.2.1.22 (cystathionine beta-synthase) inhibitor; nootropic agent
carnitine [no description available]	2.31	1	0	amino-acid betaine	human metabolite; mouse metabolite
catechol [no description available]	3.42	7	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).	3.11	4	0	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
choline [no description available]	8.33	6	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.	2.6	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.	4.88	10	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.	3.07	5	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.	2.79	3	0	chlorine molecular entity; gas molecular entity; hydrogen halide; mononuclear parent hydride	mouse metabolite
coumarin 2H-chromen-2-one: coumarin derivative	4.95	6	0	coumarins	fluorescent dye; human metabolite; plant 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).	6.4	21	0	monohydroxybenzoic acid	algal metabolite; antifungal agent; antiinfective agent; EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor; keratolytic drug; plant hormone; plant metabolite
3-methylcatechol 3-methylbenzene-1,2-diol: structure in first source. dihydroxytoluene : Any hydroxytoluene that has two hydroxy substituents. 3-methylcatechol : A methylcatechol carrying a methyl substituent at position 3. It is a xenobiotic metabolite produced by some bacteria capable of degrading nitroaromatic compounds present in pesticide-contaminated soil samples.	2.05	1	0	methylcatechol	bacterial xenobiotic metabolite
digallic acid digallic acid: structure given in first source	1.99	1	0	benzoate ester; gallate ester
octane Octanes: Eight-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives.. octane : A straight chain alkane composed of 8 carbon atoms.	2.02	1	0	alkane	xenobiotic
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.	3.53	8	0	benzenetriol; phenolic donor	algal metabolite
gallic acid gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.	10.1	95	2	trihydroxybenzoic acid	antineoplastic agent; antioxidant; apoptosis inducer; astringent; cyclooxygenase 2 inhibitor; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; geroprotector; human xenobiotic metabolite; plant 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.	3.81	3	0	medium-chain fatty acid; straight-chain saturated fatty acid	antibacterial agent; Escherichia coli metabolite; human metabolite
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.	3.81	3	0	aminophenol	allergen; metabolite
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.	3.78	2	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.	3.29	6	0	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.	3.57	8	0	2-hydroxydicarboxylic acid; C4-dicarboxylic acid	food acidity regulator; fundamental metabolite
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.	2.39	2	0	catechols; dihydroxyphenylacetic acid	human metabolite
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.	3.16	5	0	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
dimethylglycine dimethylglycine: metabolic product of calcium pangamate; mutagen when mixed with nitrite; RN given refers to parent cpd. N,N-dimethylglycine : An N-methylglycine that is glycine carrying two N-methyl substituents.	2.02	1	0	amino acid zwitterion; N-methyl-amino acid; N-methylglycines	Daphnia magna metabolite; human metabolite; mouse 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.	2.58	2	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	2.37	2	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]	2.7	3	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
glyceraldehyde Glyceraldehyde: An aldotriose containing the propionaldehyde structure with hydroxy groups at the 2- and 3-positions. It is involved in the formation of ADVANCED GLYCOSYLATION END PRODUCTS.. glyceraldehyde : An aldotriose comprising propanal having hydroxy groups at the 2- and 3-positions. It plays role in the formation of advanced glycation end-products (AGEs), a deleterious accompaniment to ageing.. aldose : Aldehydic parent sugars (polyhydroxy aldehydes H[CH(OH)]nC(=O)H, n >= 2) and their intramolecular hemiacetals.	2.37	2	0	aldotriose	fundamental metabolite
glycerol Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.	2.43	2	0	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
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.	2.42	2	0	carbon oxoanion	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
histamine [no description available]	8.35	6	0	aralkylamino compound; imidazoles	human metabolite; mouse metabolite; neurotransmitter
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.	2.13	1	0	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
hydroquinone [no description available]	4.02	4	0	benzenediol; hydroquinones	antioxidant; carcinogenic agent; cofactor; Escherichia coli metabolite; human xenobiotic metabolite; mouse metabolite; skin lightening agent
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.	3.3	6	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..	2.31	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.	3.04	5	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.	2.46	2	0	piperidinemonocarboxylic acid
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.	2.01	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.	3.46	7	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.	10.83	27	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.	2.4	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.	2.81	3	0	cyclitol; hexol
melatonin [no description available]	2.44	2	0	acetamides; tryptamines	anticonvulsant; central nervous system depressant; geroprotector; hormone; human metabolite; immunological adjuvant; mouse metabolite; radical scavenger
naringenin [no description available]	2.13	1	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.	10.33	3	1	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.	5.28	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.	4.41	6	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.	5.54	16	1	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
nitroxyl nitroxyl: hydroxamic acid oxidized to nitroxyl free radical. nitroxyl : A nitrogen oxoacid consisting of an oxygen atom double-bonded to an NH group.	4.8	1	1	nitrogen oxoacid
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)	5.28	12	1	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species	human metabolite
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
hydroxide ion [no description available]	2.21	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.	2.6	1	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
triphosphoric acid triphosphoric acid: used as water softener, peptizing agent, emulsifier & dispersing agent; ingredient of cleansers; meat preservative; RN given refers to parent cpd; structure	2.15	1	0	acyclic phosphorus acid anhydride; phosphorus oxoacid
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.	3.02	4	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
phenol [no description available]	9.98	11	0	phenols	antiseptic drug; disinfectant; human xenobiotic metabolite; mouse 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.	2.01	1	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
phosphoric acid phosphoric acid: concise etchant is 37% H3PO4. phosphoric acid : A phosphorus oxoacid that consists of one oxo and three hydroxy groups joined covalently to a central phosphorus atom.	2.1	1	0	phosphoric acids	algal metabolite; fertilizer; human metabolite; NMR chemical shift reference compound; solvent
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	0	pyridinemonocarboxylic acid	human metabolite; MALDI matrix material
propionic acid propionic acid : A short-chain saturated fatty acid comprising ethane attached to the carbon of a carboxy group.	7.52	2	0	saturated fatty acid; short-chain fatty acid	antifungal drug
purine 1H-purine : The 1H-tautomer of purine.. 3H-purine : The 3H-tautomer of purine.. 9H-purine : The 9H-tautomer of purine.. 7H-purine : The 7H-tautomer of purine.	7.02	1	0	purine
putrescine [no description available]	2.71	3	0	alkane-alpha,omega-diamine	antioxidant; fundamental metabolite
pyrazinamide pyrazinecarboxamide : A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of pyrazinoic acid (pyrazine-2-carboxylic acid) with ammonia. A prodrug for pyrazinoic acid, pyrazinecarboxamide is used as part of multidrug regimens for the treatment of tuberculosis.	2.05	1	0	monocarboxylic acid amide; N-acylammonia; pyrazines	antitubercular agent; prodrug
pyrazinoic acid pyrazinoic acid: active metabolite of pyrazinamide; structure. pyrazine-2-carboxylic acid : The parent compound of the class of pyrazinecarboxylic acids, that is pyrazine bearing a single carboxy substituent. The active metabolite of the antitubercular drug pyrazinamide.	2.05	1	0	pyrazinecarboxylic acid	antitubercular agent; drug metabolite
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.	1.99	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
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).	3.39	1	1	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.	6.18	10	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.	2.44	2	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.	2	1	0	pyridinedicarboxylic acid	Escherichia coli metabolite; human metabolite; mouse metabolite; NMDA receptor agonist
sarcosine cocobetaine: N-alkyl-betaine; cause of shampoo dermatitis	2.02	1	0	N-alkylglycine zwitterion; N-alkylglycine; N-methyl-amino acid; N-methylglycines	Escherichia coli metabolite; glycine receptor agonist; glycine transporter 1 inhibitor; human metabolite; mouse metabolite
selenious acid Selenious Acid: A selenium compound with the molecular formula H2SO3. It used as a source of SELENIUM, especially for patients that develop selenium deficiency following prolonged PARENTERAL NUTRITION.	2.13	1	0	selenium oxoacid
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).	2.77	3	0	divalent inorganic anion; sulfur oxide; sulfur oxoanion
spermidine [no description available]	2.02	1	0	polyazaalkane; triamine	autophagy inducer; fundamental metabolite; geroprotector
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.	5.25	3	1	alpha,omega-dicarboxylic acid; C4-dicarboxylic acid	anti-ulcer drug; fundamental metabolite; micronutrient; nutraceutical; radiation protective agent
sulfur dioxide Sulfur Dioxide: A highly toxic, colorless, nonflammable gas. It is used as a pharmaceutical aid and antioxidant. It is also an environmental air pollutant.	2.1	1	0	sulfur oxide	Escherichia coli metabolite; food bleaching agent; refrigerant
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.	8.05	5	0	primary alcohol; vitamin B1	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
thymine [no description available]	1.94	1	0	pyrimidine nucleobase; pyrimidone	Escherichia coli metabolite; human metabolite; mouse metabolite
toluene methylbenzene : Any alkylbenzene that is benzene substituted with one or more methyl groups.	5.27	3	1	methylbenzene; toluenes; volatile organic compound	cholinergic antagonist; fuel additive; neurotoxin; non-polar solvent
trimethyloxamine trimethyloxamine: used in manufacture of quaternary ammonium cpds; insect attractant; warming agent for gas; oxidant; structure. trimethylamine N-oxide : A tertiary amine oxide resulting from the oxidation of the amino group of trimethylamine.	3.08	4	0	tertiary amine oxide	Escherichia coli metabolite; metabolite; osmolyte
trimethylamine [no description available]	3.11	3	0	methylamines; tertiary amine	Escherichia coli metabolite; human xenobiotic metabolite
tryptophan [no description available]	3.1	1	0	alpha-amino acid; amino acid zwitterion; aminoalkylindole; aromatic amino acid; polar amino acid	Daphnia magna 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.	6.92	11	1	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.	5.18	3	1	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).	4.1	4	0	benzaldehydes; monomethoxybenzene; phenols	anti-inflammatory agent; anticonvulsant; antioxidant; flavouring agent; plant metabolite
isocitric acid isocitric acid: RN given refers to unlabeled parent cpd. isocitric acid : A tricarboxylic acid that is propan-1-ol with a hydrogen at each of the 3 carbon positions replaced by a carboxy group.	7.15	1	0	secondary alcohol; tricarboxylic acid	fundamental metabolite
catechin [no description available]	4.37	6	0	hydroxyflavan
epibatidine [no description available]	2.07	1	0	alkaloid
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.	2.17	1	0	non-proteinogenic alpha-amino acid
menthol Menthol: A monoterpene cyclohexanol produced from mint oils.	3.1	1	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]	2.31	1	0	catechin
mandelic acid SAMMA: mandelic acid condensation polymer	2.05	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	7.05	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.	2.41	1	0	hydrazines	alkylating agent; carcinogenic agent
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.	4.37	18	0	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine: A dopaminergic neurotoxic compound which produces irreversible clinical, chemical, and pathological alterations that mimic those found in Parkinson disease.. 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine : A tetrahydropyridine that is 1,2,3,6-tetrahydropyridine substituted by a methyl group at position 1 and a phenyl group at position 4.	2.76	2	0	methylpyridines; phenylpyridine; tetrahydropyridine	neurotoxin
1-methylimidazole 1-methyl-1H-imidazole : A 1H-imidazole having a methyl substituent at the N-1 position.	2.41	1	0	imidazoles
2-aminofluorene [no description available]	3.5	2	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.	7.38	2	0	alkanethiol; primary alcohol	geroprotector
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.	2.01	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.	7.15	1	0	C-nitro compound	antimycobacterial drug; EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor; mycotoxin; neurotoxin
pleconaril WIN 63843: structure given in first source	2.08	1	0
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.	3.1	1	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.	2.01	1	0	1-pyrroline nitrones	neuroprotective agent; spin trapping reagent
phenytoin [no description available]	2.54	2	0	imidazolidine-2,4-dione	anticonvulsant; drug allergen; sodium channel blocker; teratogenic agent
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.	2.41	1	0	indole-3-acetic acids	drug metabolite; human metabolite; mouse metabolite
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.	2.05	1	0	dihydroxyflavone	antidepressant; antineoplastic agent; antioxidant; plant metabolite; tropomyosin-related kinase B receptor agonist
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.	3.52	2	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.	3.93	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	2.7	3	0	monoazo compound
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.	5	11	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
albendazole [no description available]	4.8	1	1	aryl sulfide; benzimidazoles; benzimidazolylcarbamate fungicide; carbamate ester	anthelminthic drug; microtubule-destabilising agent; tubulin modulator
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.	2.07	1	0	secondary alcohol; secondary amino compound	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; sympatholytic agent
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.	2.51	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.	2.06	1	0	N-acylglycine	Daphnia magna metabolite
theophylline [no description available]	8.48	7	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
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.	3.1	1	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.	2.15	1	0	dihydropyridine; ethyl ester; methyl ester; monochlorobenzenes; primary amino compound	antihypertensive agent; calcium channel blocker; vasodilator agent
anastrozole [no description available]	2.41	1	0	nitrile; triazoles	antineoplastic agent; EC 1.14.14.14 (aromatase) inhibitor
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.	2.07	1	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.	2.02	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.	6.96	1	0	enoate ester; methyl ester; pyridine alkaloid; tetrahydropyridine	metabolite; muscarinic agonist
aristolochic acid i aristolochic acid I: phospholipase A inhibitor. aristolochic acid A : An aristolochic acid that is phenanthrene-1-carboxylic acid that is substituted by a methylenedioxy group at the 3,4 positions, by a methoxy group at position 8, and by a nitro group at position 10. It is the most abundant of the aristolochic acids and is found in almost all Aristolochia (birthworts or pipevines) species. It has been tried in a number of treatments for inflammatory disorders, mainly in Chinese and folk medicine. However, there is concern over their use as aristolochic acid is both carcinogenic and nephrotoxic.	2.07	1	0	aristolochic acids; aromatic ether; C-nitro compound; cyclic acetal; monocarboxylic acid; organic heterotetracyclic compound	carcinogenic agent; metabolite; mutagen; nephrotoxin; toxin
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.	4.39	6	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
baclofen [no description available]	2.05	1	0	amino acid zwitterion; gamma-amino acid; monocarboxylic acid; monochlorobenzenes; primary amino compound	central nervous system depressant; GABA agonist; muscle relaxant
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.	2.9	4	0	ortho- and peri-fused polycyclic arene	carcinogenic agent; mouse metabolite
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.	2.41	2	0	pyrrolidines; tertiary amine	anti-arrhythmia drug; antihypertensive agent; calcium channel blocker; vasodilator agent
berberine [no description available]	10.12	9	1	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
5-methoxypsoralen 5-Methoxypsoralen: A linear furanocoumarin that has phototoxic and anti-inflammatory properties, with effects similar to METHOXSALEN. It is used in PUVA THERAPY for the treatment of PSORIASIS.. 5-methoxypsoralen : A 5-methoxyfurocoumarin that is psoralen substituted by a methoxy group at position 5.	2.5	2	0	5-methoxyfurocoumarin; organic heterotricyclic compound; psoralens	hepatoprotective agent; plant metabolite
2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one: from maize extracts; structure given in first source. DIMBOA : A lactol that is DIBOA in which the hydrogen at position 7 is replaced by a methoxy group. It has been isolated from the maize plants.	2.05	1	0	aromatic ether; benzoxazine; cyclic hydroxamic acid; lactol	allelochemical; plant metabolite
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
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.	2.05	1	0	carbamate ester; quaternary ammonium ion	muscarinic agonist
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.	2.11	1	0	bibenzimidazole; N-methylpiperazine	anthelminthic drug; fluorochrome
bronopol [no description available]	2.31	1	0	nitro compound
bumetanide [no description available]	3.1	1	0	amino acid; benzoic acids; sulfonamide	diuretic; EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor
caffeine [no description available]	16.92	181	16	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.	2.49	2	0	aromatic ether; nitrile; polyether; tertiary amino compound
N-[4-methyl-1-oxo-1-(1-oxohexan-2-ylamino)pentan-2-yl]carbamic acid (phenylmethyl) ester [no description available]	2.31	1	0	leucine derivative
camphor, (+-)-isomer [no description available]	2.41	1	0	bornane monoterpenoid; cyclic monoterpene ketone	plant metabolite
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.	3.53	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
carmofur [no description available]	2.31	1	0	organohalogen compound; pyrimidines
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.	2.05	1	0	quaternary ammonium ion
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.	5.05	2	1	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.	3.57	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.	3.1	1	0	organochlorine compound; phenothiazines; tertiary amine	anticoronaviral agent; antiemetic; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; phenothiazine antipsychotic drug
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.	2.07	1	0	aliphatic sulfide; guanidines; imidazoles; nitrile	adjuvant; analgesic; anti-ulcer drug; H2-receptor antagonist; P450 inhibitor
eucalyptol [no description available]	3.91	3	0
ciprofibrate [no description available]	3.1	1	0	cyclopropanes; monocarboxylic acid; organochlorine compound	antilipemic drug
clofibrate angiokapsul: contains clofibrate & insoitolnicotinate	3.1	1	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
4-chloro-N-(2,6-dimethyl-1-piperidinyl)-3-sulfamoylbenzamide [no description available]	3.1	1	0	sulfonamide
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
cypermethrin cypermethrin : A carboxylic ester resulting from the formal condensation between 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid and the alcoholic hydroxy group of hydroxy(3-phenoxyphenyl)acetonitrile.. zeta-cypermethrin : A diastereoisomeric mixture comprising the isomeric pair (1R)-cis-(alphaS)- and (1S)-trans-(alphaR)-cypermethrin together with the isomeric pair (1S)-cis-(alphaS)- and (1S)-trans-(alphaS)-cypermethrin where the ratio between the isomeric pairs lies in the range 45:55 to 55:45.	2.01	1	0	aromatic ether; cyclopropanecarboxylate ester; nitrile; organochlorine compound	agrochemical; molluscicide; pyrethroid ester acaricide; pyrethroid ester insecticide
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
danthron danthron: structure. chrysazin : A dihydroxyanthraquinone that is anthracene-9,10-dione substituted by hydroxy groups at positions 1 and 8.	3.1	1	0	dihydroxyanthraquinone	apoptosis inducer; plant metabolite
dapi DAPI: RN given refers to parent cpd.	2.13	1	0	indoles	fluorochrome
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.	3.53	2	0	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; anti-inflammatory agent; antibacterial agent; human metabolite; plant metabolite; volatile oil component
2,3-dimethoxy-5-methyl-6-decyl-1,4-benzoquinone 2,3-dimethoxy-5-methyl-6-decyl-1,4-benzoquinone: ubiquinol analog. 6-decylubiquinone : A member of the class of 1,4-benzoquinones that is 2,3-dimethoxybenzoquinone which has been substituted at positions 5 and 6 by decyl and methyl groups.	2.07	1	0	1,4-benzoquinones	cofactor
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.	3.1	1	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.	2.07	1	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.	2.04	1	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
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.	7.59	2	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
3,4-dihydroxybenzohydroxamic acid [no description available]	1.99	1	0	benzoic acids
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
3,3'-diindolylmethane 3,3'-diindolylmethane: anti-inflammatory from edible cruciferous vegetables; a cytochrome P-450 antagonist	2.07	1	0	indoles	antineoplastic agent; P450 inhibitor
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.	3.86	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
disulfiram [no description available]	2.31	1	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.	3.52	2	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
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.	7.63	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
ebselen ebselen : A benzoselenazole that is 1,2-benzoselenazol-3-one carrying an additional phenyl substituent at position 2. Acts as a mimic of glutathione peroxidase.	2.31	1	0	benzoselenazole	anti-inflammatory drug; antibacterial agent; anticoronaviral agent; antifungal agent; antineoplastic agent; antioxidant; apoptosis inducer; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor; EC 2.5.1.7 (UDP-N-acetylglucosamine 1-carboxyvinyltransferase) inhibitor; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor; EC 3.1.3.25 (inositol-phosphate phosphatase) inhibitor; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; EC 3.5.4.1 (cytosine deaminase) inhibitor; EC 5.1.3.2 (UDP-glucose 4-epimerase) inhibitor; enzyme mimic; ferroptosis inhibitor; genotoxin; hepatoprotective agent; neuroprotective agent; radical scavenger
ellipticine ellipticine : A organic heterotetracyclic compound that is pyrido[4,3-b]carbazole carrying two methyl substituents at positions 5 and 11.	2.07	1	0	indole alkaloid; organic heterotetracyclic compound; organonitrogen heterocyclic compound; polycyclic heteroarene	antineoplastic agent; plant metabolite
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.	2.07	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.	4.78	5	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.	2.47	2	0
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.	3.1	1	0	aromatic ether; aromatic ketone; dichlorobenzene; monocarboxylic acid	EC 2.5.1.18 (glutathione transferase) inhibitor; ion transport inhibitor; loop diuretic
ethylenediamine ethylenediamine: RN given refers to parent cpd; edamine is the recommended contraction for the ethylenediamine radical. ethylenediamine : An alkane-alpha,omega-diamine in which the alkane is ethane.	2.15	1	0	alkane-alpha,omega-diamine	GABA agonist
etodolac Etodolac: A non-steroidal anti-inflammatory agent and cyclooxygenase-2 (COX-2) inhibitor with potent analgesic and anti-arthritic properties. It has been shown to be effective in the treatment of OSTEOARTHRITIS; RHEUMATOID ARTHRITIS; ANKYLOSING SPONDYLITIS; and in the alleviation of postoperative pain (PAIN, POSTOPERATIVE).. etodolac : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl moiety. A preferential inhibitor of cyclo-oxygenase 2 and non-steroidal anti-inflammatory, it is used for the treatment of rheumatoid arthritis and osteoarthritis, and for the alleviation of postoperative pain. Administered as the racemate, only the (S)-enantiomer is active.	2.15	1	0	monocarboxylic acid; organic heterotricyclic compound	antipyretic; cyclooxygenase 2 inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
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.	2.04	1	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.	2.07	1	0	dichlorobenzene; dihydropyridine; ethyl ester; methyl ester	anti-arrhythmia drug; antihypertensive agent; calcium channel blocker; vasodilator agent
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
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.	2.51	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.	2.11	1	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]	3.1	1	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.	2.03	1	0	ethyl ester; imidazobenzodiazepine; organofluorine compound	antidote to benzodiazepine poisoning; GABA antagonist
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.	7.11	1	0	nucleobase analogue; organofluorine compound	antimetabolite; antineoplastic agent; environmental contaminant; immunosuppressive agent; radiosensitizing agent; xenobiotic
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.	3.57	2	0	chlorobenzoic acid; furans; sulfonamide	environmental contaminant; loop diuretic; xenobiotic
fusaric acid Fusaric Acid: A picolinic acid derivative isolated from various Fusarium species. It has been proposed for a variety of therapeutic applications but is primarily used as a research tool. Its mechanisms of action are poorly understood. It probably inhibits DOPAMINE BETA-HYDROXYLASE, the enzyme that converts dopamine to norepinephrine. It may also have other actions, including the inhibition of cell proliferation and DNA synthesis.	2	1	0	aromatic carboxylic acid; pyridines
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.	2.25	1	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.	3.25	1	0	dihydroxybenzoic acid	EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; fungal metabolite; human metabolite; MALDI matrix material; mouse metabolite
glutaral Glutaral: One of the protein CROSS-LINKING REAGENTS that is used as a disinfectant for sterilization of heat-sensitive equipment and as a laboratory reagent, especially as a fixative.. glutaraldehyde : A dialdehyde comprised of pentane with aldehyde functions at C-1 and C-5.	2.6	1	0	dialdehyde	cross-linking reagent; disinfectant; fixative
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.	2.78	3	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
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.	2.78	3	0
guaifenesin Guaifenesin: An expectorant that also has some muscle relaxing action. It is used in many cough preparations.	2.21	1	0	methoxybenzenes
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.	2.31	1	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.	2.13	1	0	phosphocholines; phospholipid	anti-inflammatory agent; anticoronaviral agent; antifungal agent; antineoplastic agent; antiprotozoal drug; apoptosis inducer; immunomodulator; protein kinase inhibitor
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.	1.94	1	0	barbiturates
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.	7.52	2	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.	7.06	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
hypericin [no description available]	3.76	10	0
ibuprofen Midol: combination of cinnamedrine, phenacetin, aspirin & caffeine	3.53	2	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.	2.07	1	0	benzenes; monocarboxylic acid amide; tertiary amino compound	anti-arrhythmia drug; drug allergen; environmental contaminant; local anaesthetic; xenobiotic
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.	3.53	2	0	dibenzoazepine	adrenergic uptake inhibitor; antidepressant; EC 3.4.21.26 (prolyl oligopeptidase) 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.	7.77	3	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.	5.45	11	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
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.	2.17	1	0	3-isobutyl-1-methylxanthine
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.	3.36	6	0	catechols; secondary alcohol; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; cardiotonic drug; sympathomimetic agent
nsc 664704 kenpaullone: inhibits CDK1/cyclin B; structure in first source. kenpaullone : An indolobenzazepine that is paullone in which the hydrogen at position 9 is replaced by a bromo substituent. It is an ATP-competitive inhibitor of cyclin-dependent kinases (CDKs) and glycogen synthase kinase 3beta (GSK3beta).	2.07	1	0	indolobenzazepine; lactam; organobromine compound	cardioprotective agent; EC 2.7.11.22 (cyclin-dependent kinase) inhibitor; EC 2.7.11.26 (tau-protein kinase) inhibitor; geroprotector
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.	3.53	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
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.	2.07	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.	2.74	3	0	6-aminopurines; furans	cytokinin; geroprotector
kojic acid [no description available]	2.77	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
mimosine Mimosine: 3-Hydroxy-4-oxo-1(4H)-pyridinealanine. An antineoplastic alanine-substituted pyridine derivative isolated from Leucena glauca.	2.03	1	0	alpha-amino acid
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.	3.1	1	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
lapachol lapachol : A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone substituted by hydroxy and 3-methylbut-2-en-1-yl groups at positions 2 and 3, respectively. It is a natural compound that exhibits antibacterial and anticancer properties, first isolated in 1882 from the bark of Tabebuia avellanedae.	2.25	1	0
beta-lapachone beta-lapachone: antineoplastic inhibitor of reverse transcriptase, DNA topoisomerase, and DNA polymerase. beta-lapachone : A benzochromenone that is 3,4-dihydro-2H-benzo[h]chromene-5,6-dione substituted by geminal methyl groups at position 2. Isolated from Tabebuia avellanedae, it exhibits antineoplastic and anti-inflammatory activities.	2.54	2	0	benzochromenone; orthoquinones	anti-inflammatory agent; antineoplastic agent; plant metabolite
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.	4.06	4	0	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; antibacterial agent; plant metabolite
lavendustin a lavendustin A: from Streptomyces griseolavendus; structure given in first source	2.07	1	0	aromatic amine
lavendustin b [no description available]	2.07	1	0
leflunomide Leflunomide: An isoxazole derivative that inhibits dihydroorotate dehydrogenase, the fourth enzyme in the pyrimidine biosynthetic pathway. It is used an immunosuppressive agent in the treatment of RHEUMATOID ARTHRITIS and PSORIATIC ARTHRITIS.. leflunomide : A monocarboxylic acid amide obtained by formal condensation of the carboxy group of 5-methyl-1,2-oxazole-4-carboxylic acid with the anilino group of 4-(trifluoromethyl)aniline. The prodrug of teriflunomide.	2.05	1	0	(trifluoromethyl)benzenes; isoxazoles; monocarboxylic acid amide	antineoplastic agent; antiparasitic agent; EC 1.3.98.1 [dihydroorotate oxidase (fumarate)] inhibitor; EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; hepatotoxic agent; immunosuppressive agent; non-steroidal anti-inflammatory drug; prodrug; pyrimidine synthesis inhibitor; tyrosine kinase inhibitor
letrozole [no description available]	2.41	1	0	nitrile; triazoles	antineoplastic agent; EC 1.14.14.14 (aromatase) inhibitor
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	3.1	1	0	biphenylyltetrazole; imidazoles	angiotensin receptor antagonist; anti-arrhythmia drug; antihypertensive agent; endothelin receptor antagonist
loxapine Loxapine: An antipsychotic agent used in SCHIZOPHRENIA.	3.1	1	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	2.13	1	0	chromones; morpholines; organochlorine compound	autophagy inhibitor; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor; geroprotector
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.	2.54	2	0	1,4-naphthoquinones; vitamin K	angiogenesis inhibitor; antineoplastic agent; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; human urinary metabolite; nutraceutical
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.	3.1	1	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.	3.55	2	0	amino acid; aromatic amine; monocarboxylic acid; monohydroxybenzoic acid; phenols	non-steroidal anti-inflammatory drug
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.	6.63	7	2	guanidines	environmental contaminant; geroprotector; hypoglycemic agent; xenobiotic
methacrylic acid methacrylic acid: RN given refers to parent cpd. methacrylic acid : An alpha,beta-unsaturated monocarboxylic acid that is acrylic acid in which the hydrogen at position 2 is substituted by a methyl group.	2.46	2	0	alpha,beta-unsaturated monocarboxylic acid
methoxsalen Methoxsalen: A naturally occurring furocoumarin compound found in several species of plants, including Psoralea corylifolia. It is a photoactive substance that forms DNA ADDUCTS in the presence of ultraviolet A irradiation.. methoxsalen : A member of the class of psoralens that is 7H-furo[3,2-g]chromen-7-one in which the 9 position is substituted by a methoxy group. It is a constituent of the fruits of Ammi majus. Like other psoralens, trioxsalen causes photosensitization of the skin. It is administered topically or orally in conjunction with UV-A for phototherapy treatment of vitiligo and severe psoriasis.	2.5	2	0	aromatic ether; psoralens	antineoplastic agent; cross-linking reagent; dermatologic drug; photosensitizing agent; plant metabolite
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.	2.1	1	0	benzoate ester; methyl ester; salicylates	flavouring agent; insect attractant; metabolite
methyl methanesulfonate [no description available]	2.42	2	0	methanesulfonate ester	alkylating agent; apoptosis inducer; carcinogenic agent; genotoxin; mutagen
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.	2.07	1	0	aromatic ether; propanolamine; secondary alcohol; secondary amino compound	antihypertensive agent; beta-adrenergic antagonist; environmental contaminant; geroprotector; xenobiotic
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.	3.1	1	0	aromatic ether; primary amino compound	anti-arrhythmia drug
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.	2.41	1	0	dialkylarylamine; tertiary amino compound
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.	3.5	2	0	dihydroxyanthraquinone	analgesic; antineoplastic agent
entinostat [no description available]	2.13	1	0	benzamides; carbamate ester; primary amino compound; pyridines; substituted aniline	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor
myristicin myristicin: asaricin is an isomer; structure; a methylene dioxy version of elemicin;	2.07	1	0	organic molecular entity	metabolite
nalidixic acid [no description available]	2.53	2	0	1,8-naphthyridine derivative; monocarboxylic acid; quinolone antibiotic	antibacterial drug; antimicrobial agent; DNA synthesis inhibitor
nevirapine Nevirapine: A potent, non-nucleoside reverse transcriptase inhibitor used in combination with nucleoside analogues for treatment of HIV INFECTIONS and AIDS.. nevirapine : A dipyridodiazepine that is 5,11-dihydro-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepine which is substituted by methyl, oxo, and cyclopropyl groups at positions 4, 6, and 11, respectively. A non-nucleoside reverse transcriptase inhibitor with activity against HIV-1, it is used in combination with other antiretrovirals for the treatment of HIV infection.	2.07	1	0	cyclopropanes; dipyridodiazepine	antiviral drug; HIV-1 reverse transcriptase inhibitor
niclosamide Niclosamide: An antihelmintic that is active against most tapeworms. (From Martindale, The Extra Pharmacopoeia, 30th ed, p48). niclosamide : A secondary carboxamide resulting from the formal condensation of the carboxy group of 5-chlorosalicylic acid with the amino group of 2-chloro-4-nitroaniline. It is an oral anthelmintic drug approved for use against tapeworm infections.	2.31	1	0	benzamides; C-nitro compound; monochlorobenzenes; salicylanilides; secondary carboxamide	anthelminthic drug; anticoronaviral agent; antiparasitic agent; apoptosis inducer; molluscicide; piscicide; STAT3 inhibitor
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.	3.8	1	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.	2.07	1	0	C-nitro compound; dicarboxylic acids and O-substituted derivatives; diester; dihydropyridine; ethyl ester; methyl ester	antihypertensive agent; calcium channel blocker; geroprotector; vasodilator agent
masoprocol nordihydroguaretic acid: antioxidant compound found in the creosote bush (Larrea tridentata)	2.1	1	0	catechols; lignan; tetrol	antioxidant; ferroptosis inhibitor; geroprotector; plant metabolite
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.	3.1	1	0	organic tricyclic compound; secondary amine	adrenergic uptake inhibitor; analgesic; antidepressant; antineoplastic agent; apoptosis inducer; drug metabolite
6,7-dimethoxy-3-(4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3H-isobenzofuran-1-one [no description available]	2.07	1	0	isoquinolines
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.	2.01	1	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.	2.42	2	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.	4.8	1	1	3-oxo monocarboxylic acid; N-arylpiperazine; N-methylpiperazine; organofluorine compound; oxazinoquinoline
omeprazole Omeprazole: A 4-methoxy-3,5-dimethylpyridyl, 5-methoxybenzimidazole derivative of timoprazole that is used in the therapy of STOMACH ULCERS and ZOLLINGER-ELLISON SYNDROME. The drug inhibits an H(+)-K(+)-EXCHANGING ATPASE which is found in GASTRIC PARIETAL CELLS.. omeprazole : A racemate comprising equimolar amounts of (R)- and (S)-omeprazole.. 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole : A member of the class of benzimidazoles that is 1H-benzimidazole which is substituted by a [4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl group at position 2 and a methoxy group at position 5.	2.08	1	0	aromatic ether; benzimidazoles; pyridines; sulfoxide
oxonic acid Oxonic Acid: Antagonist of urate oxidase.	2.57	2	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).	2.72	2	0	benzenetriol; catecholamine; primary amino compound	drug metabolite; human metabolite; neurotoxin
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.	3.1	1	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).	3.43	7	0	1,4-benzoquinones	cofactor; human xenobiotic metabolite; mouse metabolite
1,7-dimethylxanthine 1,7-dimethylxanthine : A dimethylxanthine having the two methyl groups located at positions 1 and 7. It is a metabolite of caffeine and theobromine in animals.	2.31	1	0	dimethylxanthine	central nervous system stimulant; human blood serum metabolite; human xenobiotic metabolite; mouse metabolite
patulin Patulin: 4-Hydroxy-4H-furo(3,2-c)pyran-2(6H)-one. A mycotoxin produced by several species of Aspergillus and Penicillium. It is found in unfermented apple and grape juice and field crops. It has antibiotic properties and has been shown to be carcinogenic and mutagenic and causes chromosome damage in biological systems.. patulin : A furopyran and lactone that is (2H-pyran-3(6H)-ylidene)acetic acid which is substituted by hydroxy groups at positions 2 and 4 and in which the hydroxy group at position 4 has condensed with the carboxy group to give the corresponding bicyclic lactone. A mycotoxin produced by several species of Aspergillus and Penicillium, it has antibiotic properties but has been shown to be carcinogenic and mutagenic.	7.57	2	0	furopyran; gamma-lactone; lactol	antimicrobial agent; Aspergillus metabolite; carcinogenic agent; mutagen; mycotoxin; Penicillium metabolite
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'.	2.47	2	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.	2.07	1	0	barbiturates	GABAA receptor agonist
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.	3.51	2	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.	3.1	1	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.	3.84	3	0	2,1-benzoxathiole; arenesulfonate ester; phenols; sultone	acid-base indicator; diagnostic agent; two-colour indicator
4-phenylbutyric acid 4-phenylbutyric acid: RN refers to the parent cpd. 4-phenylbutyric acid : A monocarboxylic acid the structure of which is that of butyric acid substituted with a phenyl group at C-4. It is a histone deacetylase inhibitor that displays anticancer activity. It inhibits cell proliferation, invasion and migration and induces apoptosis in glioma cells. It also inhibits protein isoprenylation, depletes plasma glutamine, increases production of foetal haemoglobin through transcriptional activation of the gamma-globin gene and affects hPPARgamma activation.	2.05	1	0	monocarboxylic acid	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor; prodrug
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.	3.47	2	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
phenylmethylsulfonyl fluoride Phenylmethylsulfonyl Fluoride: An enzyme inhibitor that inactivates IRC-50 arvin, subtilisin, and the fatty acid synthetase complex.. phenylmethanesulfonyl fluoride : An acyl fluoride with phenylmethanesulfonyl as the acyl group.	2.08	1	0	acyl fluoride	serine proteinase inhibitor
phloretin [no description available]	4.43	6	0	dihydrochalcones	antineoplastic agent; plant metabolite
ag 1879 3-(4-chlorophenyl)-1-(1,1-dimethylethyl)-1H-pyrazolo(3,4-d)pyrimidin-4-amine: Fyn kinase inhibitor	2.05	1	0	aromatic amine; monochlorobenzenes; pyrazolopyrimidine	beta-adrenergic antagonist; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; geroprotector
practolol Practolol: A beta-1 adrenergic antagonist that has been used in the emergency treatment of CARDIAC ARRYTHMIAS.. practolol : N-(4-Hydroxyphenyl)acetamide in which the hydrogen of the phenolic hydroxy group is substituted by a 3-(isopropylaminoamino)-2-hydroxypropyl group. A selective beta blocker, it has been used in the emergency treatment of cardiac arrhythmias.	2.07	1	0	acetamides; ethanolamines; propanolamine; secondary alcohol; secondary amino compound	anti-arrhythmia drug; beta-adrenergic antagonist
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.	3.47	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.	2.43	2	0	dithioketal; polyphenol	anti-inflammatory drug; anticholesteremic drug; antilipemic drug; antioxidant; cardiovascular drug
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.	3.1	1	0	phenothiazines; tertiary amine	anti-allergic agent; anticoronaviral agent; antiemetic; antipruritic drug; H1-receptor antagonist; local anaesthetic; sedative
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.	7.46	2	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.	3.53	2	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.	3.1	1	0	trihydroxybenzoic acid
protoporphyrin ix protoporphyrin IX: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7685. protoporphyrin : A cyclic tetrapyrrole that consists of porphyrin bearing four methyl substituents at positions 3, 8, 13 and 17, two vinyl substituents at positions 7 and 12 and two 2-carboxyethyl substituents at positions 2 and 18. The parent of the class of protoporphyrins.	2.31	1	0
pseudohypericin pseudohypericin: structure given in first source	2.97	4	0
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.	3.1	1	0	aromatic ether; ethylenediamine derivative	H1-receptor antagonist
pyrimethamine Maloprim: contains above 2 cpds	4.8	1	1	aminopyrimidine; monochlorobenzenes	antimalarial; antiprotozoal drug; EC 1.5.1.3 (dihydrofolate reductase) inhibitor
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.	3.5	2	0	tetrahydroxyanthraquinone	EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor
3-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-5-iodo-1H-indol-2-one [no description available]	2.31	1	0	indoles
opc 12759 rebamipide: structure in first source; RN refers to (+-)-isomer; inhibits gastric xanthine oxidase	2.15	1	0	secondary carboxamide
rimantadine Rimantadine: An RNA synthesis inhibitor that is used as an antiviral agent in the prophylaxis and treatment of influenza.	2.93	1	0	alkylamine
4-(3-butoxy-4-methoxybenzyl)-2-imidazolidinone 4-(3-Butoxy-4-methoxybenzyl)-2-imidazolidinone: Inhibitor of phosphodiesterases.	2.17	1	0	methoxybenzenes
rofecoxib [no description available]	2.01	1	0	butenolide; sulfone	analgesic; cyclooxygenase 2 inhibitor; non-steroidal anti-inflammatory drug
salicylamide salamide: a major impurity of hydrochlorothiazide; structure in first source	3.1	1	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.	2.07	1	0	alkaloid antibiotic; benzophenanthridine alkaloid; botanical anti-fungal agent
alkannin [no description available]	2.31	1	0	naphthoquinone
sodium fluoride [no description available]	5.06	2	1	fluoride salt	mutagen
4-phenylbutyric acid, sodium salt sodium phenylbutyrate : The organic sodium salt of 4-phenylbutyric acid. A prodrug for phenylacetate, it is used to treat urea cycle disorders.	2.05	1	0	organic sodium salt	EC 3.5.1.98 (histone deacetylase) inhibitor; geroprotector; neuroprotective agent; orphan drug; prodrug
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.	2.05	1	0	long-chain fatty acid; saturated fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; human metabolite; plant metabolite
streptonigrin [no description available]	2.07	1	0	pyridines; quinolone	antimicrobial agent; antineoplastic agent
vorinostat Vorinostat: A hydroxamic acid and anilide derivative that acts as a HISTONE DEACETYLASE inhibitor. It is used in the treatment of CUTANEOUS T-CELL LYMPHOMA and SEZARY SYNDROME.. vorinostat : A dicarboxylic acid diamide comprising suberic (octanedioic) acid coupled to aniline and hydroxylamine. A histone deacetylase inhibitor, it is marketed under the name Zolinza for the treatment of cutaneous T cell lymphoma (CTCL).	2.05	1	0	dicarboxylic acid diamide; hydroxamic acid	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor
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
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
sulforaphane sulforaphane: from Cardaria draba L.. sulforaphane : An isothiocyanate having a 4-(methylsulfinyl)butyl group attached to the nitrogen.	2.55	2	0	isothiocyanate; sulfoxide	antineoplastic agent; antioxidant; EC 3.5.1.98 (histone deacetylase) inhibitor; plant metabolite
sulpiride Sulpiride: A dopamine D2-receptor antagonist. It has been used therapeutically as an antidepressant, antipsychotic, and as a digestive aid. (From Merck Index, 11th ed). sulpiride : A member of the class of benzamides obtained from formal condensation between the carboxy group of 2-methoxy-5-sulfamoylbenzoic acid and the primary amino group of (1-ethylpyrrolidin-2-yl)methylamine.	2.07	1	0	benzamides; N-alkylpyrrolidine; sulfonamide	antidepressant; antiemetic; antipsychotic agent; dopaminergic antagonist
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.	3.1	1	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
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]	5.96	3	2	imidazotetrazine; monocarboxylic acid amide; triazene derivative	alkylating agent; antineoplastic agent; prodrug
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.	3.1	1	0	diarylmethane
tetrahydropapaverine tetrahydropapaverine: RN given refers to parent cpd. 1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline : A benzylisoquinoline alkaloid that is norlaudanosoline in which the four phenolic hydrogens have been replaced by methyl groups.	2.07	1	0	aromatic ether; benzylisoquinoline alkaloid; benzyltetrahydroisoquinoline; polyether; secondary amino compound
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.	3.18	5	0	dimethylxanthine	adenosine receptor antagonist; bronchodilator agent; food component; human blood serum metabolite; mouse metabolite; plant metabolite; vasodilator agent
2,4-thiazolidinedione thiazolidine-2,4-dione: structure in first source. 1,3-thiazolidine-2,4-dione : A thiazolidenedione carrying oxo substituents at positions 2 and 4.	2.05	1	0	thiazolidenedione
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.	3.41	5	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
triclosan [no description available]	2.31	1	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]	3.1	1	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
trigonelline trigonelline: in hydra among other organisms; RN given refers to hydroxide inner salt; structure. N-methylnicotinic acid : A pyridinium ion consisting of nicotinic acid having a methyl substituent on the pyridine nitrogen.. N-methylnicotinate : An iminium betaine that is the conjugate base of N-methylnicotinic acid, arising from deprotonation of the carboxy group.	10.89	35	4	alkaloid; iminium betaine	food component; human urinary metabolite; plant metabolite
trioxsalen Trioxsalen: Pigmenting photosensitizing agent obtained from several plants, mainly Psoralea corylifolia. It is administered either topically or orally in conjunction with ultraviolet light in the treatment of vitiligo.. lactone : Any cyclic carboxylic ester containing a 1-oxacycloalkan-2-one structure, or an analogue having unsaturation or heteroatoms replacing one or more carbon atoms of the ring.. antipsoriatic : A drug used to treat psoriasis.. trioxsalen : 7H-Furo[3,2-g]chromen-7-one in which positions 2, 5, and 9 are substituted by methyl groups. Like other psoralens, trioxsalen causes photosensitization of the skin. It is administered orally in conjunction with UV-A for phototherapy treatment of vitiligo. After photoactivation it creates interstrand cross-links in DNA, inhibiting DNA synthesis and cell division, and can lead to cell injury; recovery from the cell injury may be followed by increased melanisation of the epidermis.	2.07	1	0	psoralens	dermatologic drug; photosensitizing agent
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]	2.47	2	0	monoamine molecular messenger; primary amino compound; tyramines	EC 3.1.1.8 (cholinesterase) inhibitor; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter
2,3-bis(2-methoxy-4-nitro-5-sulfophenyl)-5-((phenylamino)carbonyl)-2h-tetrazolium hydroxide 2,3-bis(2-methoxy-4-nitro-5-sulfophenyl)-5-((phenylamino)carbonyl)-2H-tetrazolium hydroxide: structure given in first source	2.02	1	0
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
mitomycin Mitomycin: An antineoplastic antibiotic produced by Streptomyces caespitosus. It is one of the bi- or tri-functional ALKYLATING AGENTS causing cross-linking of DNA and inhibition of DNA synthesis.. mitomycin : A family of aziridine-containing natural products isolated from Streptomyces caespitosus or Streptomyces lavendulae.	2.48	2	0	mitomycin	alkylating agent; antineoplastic agent
corticosterone [no description available]	9.47	6	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.	7.41	2	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
sorbitol D-glucitol : The D-enantiomer of glucitol (also known as D-sorbitol).	7.21	1	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.	2.81	3	0	pyrimidone	hyperglycemic agent; metabolite
thymidine [no description available]	1.94	1	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.	2.11	1	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.	3.1	1	0	2-halophenol; iodophenol; L-phenylalanine derivative; non-proteinogenic L-alpha-amino acid; thyroxine zwitterion; thyroxine	antithyroid drug; human metabolite; mouse metabolite; thyroid hormone
carbachol Carbachol: A slowly hydrolyzed CHOLINERGIC AGONIST that acts at both MUSCARINIC RECEPTORS and NICOTINIC RECEPTORS.	7.17	1	0	ammonium salt; carbamate ester	cardiotonic drug; miotic; muscarinic agonist; nicotinic acetylcholine receptor agonist; non-narcotic analgesic
aldosterone [no description available]	3.1	1	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
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.	3.53	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
pilocarpine hydrochloride pilocarpine hydrochloride : The hydrochloride salt of (+)-pilocarpine, a medication used to treat increased pressure inside the eye and dry mouth.	2.07	1	0	hydrochloride
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.	7.13	1	0	pilocarpine	antiglaucoma drug
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.	2.48	2	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.	3.55	2	0	2-halophenol; amino acid zwitterion; iodophenol; iodothyronine	human metabolite; mouse metabolite; thyroid hormone
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.	8.45	7	0	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
cantharidin Cantharidin: A toxic compound, isolated from the Spanish fly or blistering beetle (Lytta (Cantharis) vesicatoria) and other insects. It is a potent and specific inhibitor of protein phosphatases 1 (PP1) and 2A (PP2A). This compound can produce severe skin inflammation, and is extremely toxic if ingested orally.. cantharidin : A monoterpenoid with an epoxy-bridged cyclic dicarboxylic anhydride structure secreted by many species of blister beetle, and most notably by the Spanish fly, Lytta vesicatoria. Natural toxin inhibitor of protein phosphatases 1 and 2A.	2.07	1	0	cyclic dicarboxylic anhydride; monoterpenoid	EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; herbicide
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.	3.21	5	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.	2.57	2	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.	2.69	3	0	C-nitro compound; quinoline N-oxide	carcinogenic agent
chloramphenicol Amphenicol: Chloramphenicol and its derivatives.	3.1	1	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.	7.13	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.	4.8	1	1	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.	8.39	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.	2.37	2	0	pseudohalide anion	EC 1.9.3.1 (cytochrome c oxidase) inhibitor
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.	2.07	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.	9.37	19	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.	3.1	1	0	17-hydroxy steroid; 3-hydroxy steroid; terminal acetylenic compound	xenoestrogen
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.	2.91	4	0	ortho-fused polycyclic arene; tetraphenes	carcinogenic agent
aminopyrine Aminopyrine: A pyrazolone with analgesic, anti-inflammatory, and antipyretic properties but has risk of AGRANULOCYTOSIS. A breath test with 13C-labeled aminopyrine has been used as a non-invasive measure of CYTOCHROME P-450 metabolic activity in LIVER FUNCTION TESTS.. aminophenazone : A pyrazolone that is 1,2-dihydro-3H-pyrazol-3-one substituted by a dimethylamino group at position 4, methyl groups at positions 1 and 5 and a phenyl group at position 2. It exhibits analgesic, anti-inflammatory, and antipyretic properties.	2.47	2	0	pyrazolone; tertiary amino compound	antipyretic; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
uridine [no description available]	2.77	3	0	uridines	drug metabolite; fundamental metabolite; human metabolite
uridine diphosphate Uridine Diphosphate: A uracil nucleotide containing a pyrophosphate group esterified to C5 of the sugar moiety.	2.13	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.	2.07	1	0	kanamycins	bacterial metabolite
galactose galactopyranose : The pyranose form of galactose.	3.03	4	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.	2.15	1	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.	2.41	1	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	2.97	4	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.	3.06	5	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.	3.77	10	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.	7.28	32	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
veratramine veratramine: structure. veratramine : A piperidine alkaloid comprising the 14,15,16,17-tetradehydro derivative of veratraman having two hydroxy groups at the 3- and 23-positions.	2.07	1	0	piperidine alkaloid
phlorhizin [no description available]	5.57	16	1	aryl beta-D-glucoside; dihydrochalcones; monosaccharide derivative	antioxidant; plant metabolite
papaverine hydrochloride [no description available]	2.07	1	0
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.	2.93	4	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
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.	7.69	2	0	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.	2.6	1	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.	8.93	13	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.	2.07	1	0	alkaloid; colchicine	anti-inflammatory agent; gout suppressant; mutagen
yohimbine hydrochloride [no description available]	2.07	1	0
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.	2.07	1	0	antibiotic fungicide; cyclic ketone; dicarboximide; piperidine antibiotic; piperidones; secondary alcohol	anticoronaviral agent; bacterial metabolite; ferroptosis inhibitor; neuroprotective agent; protein synthesis inhibitor
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.	2.6	1	0	chloromethanes; one-carbon compound	carcinogenic agent; central nervous system drug; inhalation anaesthetic; non-polar solvent; refrigerant
gliotoxin Gliotoxin: A fungal toxin produced by various species of Trichoderma, Gladiocladium fimbriatum, Aspergillus fumigatus, and Penicillium. It is used as an immunosuppressive agent.. gliotoxin : A pyrazinoindole with a disulfide bridge spanning a dioxo-substituted pyrazine ring; mycotoxin produced by several species of fungi.	2.07	1	0	dipeptide; organic disulfide; organic heterotetracyclic compound; pyrazinoindole	antifungal agent; EC 2.5.1.58 (protein farnesyltransferase) inhibitor; immunosuppressive agent; mycotoxin; proteasome inhibitor
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
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.	2.07	1	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.	3.1	1	0	beta-lactam antibiotic; penicillin allergen; penicillin	antibacterial drug
mannitol [no description available]	4.07	3	1	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
dithionitrobenzoic acid Dithionitrobenzoic Acid: A standard reagent for the determination of reactive sulfhydryl groups by absorbance measurements. It is used primarily for the determination of sulfhydryl and disulfide groups in proteins. The color produced is due to the formation of a thio anion, 3-carboxyl-4-nitrothiophenolate.. dithionitrobenzoic acid : An organic disulfide that results from the formal oxidative dimerisation of 2-nitro-5-thiobenzoic acid. An indicator used to quantify the number or concentration of thiol groups.	2.07	1	0	nitrobenzoic acid; organic disulfide	indicator
dinitrofluorobenzene Dinitrofluorobenzene: Irritants and reagents for labeling terminal amino acid groups.. 1-fluoro-2,4-dinitrobenzene : The organofluorine compound that is benzene with a fluoro substituent at the 1-position and two nitro substituents in the 2- and 4-positions.	2.17	1	0	C-nitro compound; organofluorine compound	agrochemical; allergen; chromatographic reagent; EC 2.7.3.2 (creatine kinase) inhibitor; protein-sequencing agent; spectrophotometric reagent
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.	2.05	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.	7.67	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.	2.05	1	0	pentanol; short-chain primary fatty alcohol	human metabolite; plant metabolite
veratridine [no description available]	2.07	1	0	steroid	sodium channel modulator
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.	2.05	1	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.	7.76	3	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]	3.1	1	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.	5.42	14	1	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
isoleucine Isoleucine: An essential branched-chain aliphatic amino acid found in many proteins. It is an isomer of LEUCINE. It is important in hemoglobin synthesis and regulation of blood sugar and energy levels.. isoleucine : A 2-amino-3-methylpentanoic acid having either (2R,3R)- or (2S,3S)-configuration.. L-isoleucine : The L-enantiomer of isoleucine.	1.94	1	0	aspartate family amino acid; isoleucine; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
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.	7.78	3	0	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
ethane Ethane: A two carbon alkane with the formula H3C-CH3.. ethane : An alkane comprising of two carbon atoms.	1.95	1	0	alkane; gas molecular entity	plant metabolite; refrigerant
ethylene Plastipore: high density polyethylene sponge biocompatible material; used as posts in dental bridges	2.52	2	0	alkene; gas molecular entity	plant hormone; refrigerant
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.	3.58	8	0	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
methylene chloride Methylene Chloride: A chlorinated hydrocarbon that has been used as an inhalation anesthetic and acts as a narcotic in high concentrations. Its primary use is as a solvent in manufacturing and food technology.. dichloromethane : A member of the class of chloromethanes that is methane in which two of the hydrogens have been replaced by chlorine. A dense, non-flammible colourless liquid at room temperature (b.p. 40degreeC, d = 1.33) which is immiscible with water, it is widely used as a solvent, a paint stripper, and for the removal of caffeine from coffee and tea.	2.88	3	0	chloromethanes; volatile organic compound	carcinogenic agent; polar aprotic solvent; refrigerant
tetramethylsilane [no description available]	2	1	0	organosilicon compound	NMR chemical shift reference compound
tert-amyl alcohol 2-methylbutan-2-ol : A tertiary alcohol that is propan-1-ol in which both of the hydrogens at position 1 have been replaced by methyl groups.	2.05	1	0	aliphatic alcohol; tertiary alcohol	protic 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.	3.66	9	0	alkyl hydroperoxide	antibacterial agent; oxidising agent
gibberellic acid gibberellic acid: RN given refers to (1alpha,2beta,4aalpha,4bbeta,10beta)-isomer; structure. gibberellin A3 : A C19-gibberellin that is a pentacyclic diterpenoid responsible for promoting growth and elongation of cells in plants. Initially identified in Gibberella fujikuroi,it differs from gibberellin A1 in the presence of a double bond between C-3 and C-4.	2.07	1	0	C19-gibberellin; gibberellin monocarboxylic acid; lactone; organic heteropentacyclic compound	mouse metabolite; plant metabolite
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.	4.8	1	1	benzenes; piperidines	anaesthetic; neurotoxin; NMDA receptor antagonist; psychotropic drug
quinic acid (-)-quinic acid : The (-)-enantiomer of quinic acid.	16.25	519	10
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.	3.1	1	0	monoterpenoid; tertiary alcohol	antimicrobial agent; fragrance; plant metabolite; volatile oil component
acrylamide [no description available]	3.42	6	0	acrylamides; N-acylammonia; primary carboxamide	alkylating agent; carcinogenic agent; Maillard reaction product; mutagen; neurotoxin
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.	4.8	1	1	alpha,beta-unsaturated monocarboxylic acid	metabolite
isobutyric acid isobutyric acid: RN given refers to parent cpd. isobutyric acid : A branched fatty acid comprising propanoic acid carrying a methyl branch at C-2.	2.05	1	0	branched-chain saturated fatty acid; fatty acid 4:0; methyl-branched fatty acid	Daphnia magna metabolite; plant metabolite; volatile oil component
pantothenic acid Pantothenic Acid: A butyryl-beta-alanine that can also be viewed as pantoic acid complexed with BETA ALANINE. It is incorporated into COENZYME A and protects cells against peroxidative damage by increasing the level of GLUTATHIONE.. pantothenic acid : A member of the class of pantothenic acids that is an amide formed from pantoic acid and beta-alanine.. vitamin B5 : Any member of a group of vitamers that belong to the chemical structural class called pantothenic acids that exhibit biological activity against vitamin B5 deficiency. Deficiency of vitamin B5 is rare due to its widespread distribution in whole grain cereals, legumes and meat. Symptoms associated with vitamin B5 deficiency are difficult to asses since they are subtle and resemble those of other B vitamin deficiencies. The vitamers include (R)-pantothenic acid and its ionized and salt forms.. (R)-pantothenate : A pantothenate that is the conjugate base of (R)-pantothenic acid, obtained by deprotonation of the carboxy group.. (R)-pantothenic acid : A pantothenic acid having R-configuration.	2.21	1	0	pantothenic acid; vitamin B5	antidote to curare poisoning; geroprotector; human blood serum 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.	2.41	1	0	bisphenol	endocrine disruptor; environmental contaminant; xenobiotic; xenoestrogen
dehydrocholic acid Dehydrocholic Acid: A semisynthetic bile acid made from cholic acid. It is used as a cholagogue, hydrocholeretic, diuretic, and as a diagnostic aid.. 3,7,12-trioxo-5beta-cholanic acid : An oxo-5beta-cholanic acid in which three oxo substituents are located at positions 3, 7 and 12 on the cholanic acid skeleton.	1.94	1	0	12-oxo steroid; 3-oxo-5beta-steroid; 7-oxo steroid; oxo-5beta-cholanic acid	gastrointestinal drug
taurocholic acid Taurocholic Acid: The product of conjugation of cholic acid with taurine. Its sodium salt is the chief ingredient of the bile of carnivorous animals. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and cholerectic.. taurocholate : An organosulfonate oxoanion that is the conjugate base of taurocholic acid.. taurocholic acid : A bile acid taurine conjugate of cholic acid that usually occurs as the sodium salt of bile in mammals.	7.77	3	0	amino sulfonic acid; bile acid taurine conjugate	human metabolite
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
rhodamine b rhodamine B: RN & N1 from 9th CI Form Index; RN given refers to parent cpd; structure in Merck Index, 9th ed, #7973; TETRAETHYLRHODAMINE was see RHODAMINES 1975-93; use RHODAMINES to search TETRAETHYLRHODAMINE 1975-93. rhodamine B : An organic chloride salt having N-[9-(2-carboxyphenyl)-6-(diethylamino)-3H-xanthen-3-ylidene]-N-ethylethanaminium as the counterion. An amphoteric dye commonly used as a fluorochrome.	4.8	1	1	organic chloride salt; xanthene dye	fluorescent probe; fluorochrome; histological dye
visnagin visnagin: from Musineon divaricatum. visnagin : A furanochromone that is furo[3,2-g]chromen-5-one which is substituted at positions 4 and 7 by methoxy and methyl groups, respectively. Found in the toothpick-plant, Ammi visnaga.	2.07	1	0	aromatic ether; furanochromone; polyketide	anti-inflammatory agent; antihypertensive agent; EC 1.1.1.37 (malate dehydrogenase) inhibitor; phytotoxin; plant metabolite; vasodilator agent
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
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.	3.3	5	0	organic heteropentacyclic compound; rotenones	antineoplastic agent; metabolite; mitochondrial NADH:ubiquinone reductase inhibitor; phytogenic insecticide; piscicide; toxin
skimmianine skimmianine: furanoquinoline alkaloid from Teclea (RUTACEAE)	2.07	1	0	alkaloid antibiotic; organic heterotricyclic compound; organonitrogen heterocyclic compound; oxacycle
syrosingopine syrosingopine: was heading 1963-94; SYRINGOPINE was see SYROSINGOPINE 1977-94; use RESERPINE to search SYROSINGOPINE 1966-94	2.07	1	0	yohimban alkaloid
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.	7.6	1	0	organic cation	defoliant; herbicide
1-naphthaleneacetic acid 1-naphthaleneacetic acid: a plant growth regulator; RN given refers to parent cpd. naphthylacetic acid : A monocarboxylic acid that is naphthalene substituted by a carboxymethyl group at any position.. 1-naphthaleneacetic acid : A naphthylacetic acid substituted by a carboxymethyl group at position 1.	2.06	1	0	naphthylacetic acid	synthetic auxin
phthalide 2-benzofuran-1(3H)-one : A gamma-lactone that is 1,3-dihydro-2-benzofuran in which the hydrogens at position 1 are replaced by an oxo group.. isobenzofuranone : A 2-benzofuran containing one or more oxo groups.	2.55	2	0	2-benzofurans; gamma-lactone
gramine gramine : An aminoalkylindole that is indole carrying a dimethylaminomethyl substituent at postion 3.	2.07	1	0	aminoalkylindole; indole alkaloid; tertiary amino compound	antibacterial agent; antiviral agent; plant metabolite; serotonergic antagonist
n-vinyl-2-pyrrolidinone N-vinyl-2-pyrrolidinone: monomer of POVIDONE; structure given in first source	5.19	3	1	pyrrolidin-2-ones
2-furoic acid 2-furoic acid: RN given refers to parent cpd. furoic acid : A monocarboxylic acid that consists of a furan ring having a single carboxylic acid group on any ring position and derivatives thereof.. 2-furoic acid : A furoic acid having the carboxylic acid group located at position 2.	2.31	1	0	furoic acid	bacterial xenobiotic metabolite; human xenobiotic metabolite; inhibitor; plant metabolite; Saccharomyces cerevisiae metabolite
2-nitroaniline [no description available]	3.35	1	0
pyromellitic acid pyromellitic acid: RN given refers to parent cpd; structure. pyromellitic acid : A tetracarboxylic acid that is benzene substituted by four carboxy groups at positions 1, 2, 4 and 5 respectively.	2.31	1	0	benzoic acids; tetracarboxylic acid
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.	4.58	4	0	monoterpenoid; phenols	volatile oil component
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
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.	3.8	3	0	naphthylamine	carcinogenic agent
diphenyl diphenyl: RN given refers to unlabeled cpd; structure	2.94	3	0	aromatic fungicide; benzenes; biphenyls	antifungal agrochemical; antimicrobial food preservative
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.	3.1	1	0	hydroxybiphenyls
xanthenes Xanthenes: Compounds with three aromatic rings in linear arrangement with an OXYGEN in the center ring.	2.69	3	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.	3.1	1	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
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.	2.07	1	0	naphthoic acid	mouse metabolite; xenobiotic metabolite
creosol [no description available]	2.11	1	0	methoxybenzenes; phenols
1-phenylpropanol 1-phenylpropanol: structure in first source	3.31	6	0	organic molecular entity
synephrine [no description available]	3.23	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)	4.75	9	0	benzoate ester; paraben; phenols	antifungal agent; antimicrobial agent
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.	2.97	4	0	butan-4-olide	metabolite; neurotoxin
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.	3.48	7	0	aldehyde; furans	Maillard reaction product; metabolite
furfuryl mercaptan furfuryl mercaptan: major flavoring agent in coffee; structure in first source	2.02	1	0	heteroarene
p-tert-butyl catechol [no description available]	2.03	1	0
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
pyrrolidonecarboxylic acid Pyrrolidonecarboxylic Acid: A cyclized derivative of L-GLUTAMIC ACID. Elevated blood levels may be associated with problems of GLUTAMINE or GLUTATHIONE metabolism.. 5-oxo-L-proline : An optically active form of 5-oxoproline having L-configuration.	2.52	2	0	5-oxoproline; L-proline derivative; non-proteinogenic L-alpha-amino acid	algal 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.	2.9	3	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.	3.1	1	0	paraben	antifungal agent; antimicrobial food preservative; neuroprotective agent; plant metabolite
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'.	4.5	7	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.	2.1	1	0	methoxybenzoic acid	plant metabolite
ethylbenzene [no description available]	4.8	1	1	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.	2.05	1	0	styrenes; vinylarene; volatile organic compound	mouse metabolite; mutagen; plant metabolite
4-vinylpyridine 4-vinylpyridine: reagent for blocking cysteine function in proteins; RN given refers to parent cpd	2.21	1	0
benzylamine aminotoluene : Any member of the class of toluenes carrying one or more amino groups.	2.41	1	0	aralkylamine; primary amine	allergen; EC 3.5.5.1 (nitrilase) inhibitor; plant metabolite
4-benzylphenol 4-benzylphenol: metabolite of diphenylmethane; RN given refers to parent cpd	3.1	1	0
2-ethylhexanol [no description available]	3.1	1	0	primary alcohol	plant metabolite; volatile oil component
ethylene dibromide Ethylene Dibromide: An effective soil fumigant, insecticide, and nematocide. In humans, it causes severe burning of skin and irritation of the eyes and respiratory tract. Prolonged inhalation may cause liver necrosis. It is also used in gasoline. Members of this group have caused liver and lung cancers in rodents. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), 1,2-dibromoethane may reasonably be anticipated to be a carcinogen.. 1,2-dibromoethane : A bromoalkane that is ethane carrying bromo substituents at positions 1 and 2. It is produced by marine algae.	2.02	1	0	bromoalkane; bromohydrocarbon	algal metabolite; carcinogenic agent; fumigant; marine metabolite; mouse metabolite; mutagen
acrolein [no description available]	3.35	1	0	enal	herbicide; human xenobiotic metabolite; toxin
glyoxal [no description available]	2.42	2	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.	2.57	2	0	alkane
n-pentanoic acid n-pentanoic acid: RN given refers to unlabeled parent cpd. valeric acid : A straight-chain saturated fatty acid containing five carbon atoms.	2.05	1	0	short-chain fatty acid; straight-chain saturated fatty acid	plant metabolite
pentane Pentanes: Five-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives.. pentane : A straight chain alkane consisting of 5 carbon atoms.	2.01	1	0	alkane; volatile organic compound	non-polar solvent; refrigerant
tetrahydrofuran oxolane : A cyclic ether that is butane in which one hydrogen from each methyl group is substituted by an oxygen.	2.43	2	0	cyclic ether; oxolanes; saturated organic heteromonocyclic parent; volatile organic compound	polar aprotic solvent
furan furan : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing four carbons and one oxygen, with formula C4H4O. It is a toxic, flammable, low-boiling (31degreeC) colourless liquid.	2.25	1	0	furans; mancude organic heteromonocyclic parent; monocyclic heteroarene	carcinogenic agent; hepatotoxic agent; Maillard reaction product
isopropyl myristate isopropyl myristate: used for microemulsions; structure	2.48	2	0	fatty acid ester
n-hexane hexane : An unbranched alkane containing six carbon atoms.	2.15	1	0	alkane; volatile organic compound	neurotoxin; non-polar solvent
piperidine [no description available]	2.17	1	0	azacycloalkane; piperidines; saturated organic heteromonocyclic parent; secondary amine	base; catalyst; human metabolite; non-polar solvent; plant metabolite; protic solvent; reagent
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.	2.05	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; antifeedant; Daphnia magna metabolite; plant metabolite
undecanoic acid undecanoic acid : A straight-chain, eleven-carbon saturated medium-chain fatty acid found in body fluids; the most fungitoxic of the C7:0 - C18:0 fatty acid series.. undecanoate : A medium-chain fatty acid anion that is the conjugate base of undecanoic acid; used in tandem with testosterone cation in the treatment of male hypogonadism. Major species at pH 7.3.	2.05	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	antifungal agent; human metabolite
behenic acid behenic acid: RN given refers to parent cpd; structure. docosanoic acid : A straight-chain, C22, long-chain saturated fatty acid.	2.05	1	0	long-chain fatty acid; straight-chain saturated fatty acid	plant metabolite
methylergonovine Methylergonovine: A homolog of ERGONOVINE containing one more CH2 group. (Merck Index, 11th ed)	2.07	1	0	ergoline alkaloid
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
chloranil Chloranil: A quinone fungicide used for treatment of seeds and foliage.. tetrachloro-1,4-benzoquinone : A member of the class of 1,4-benzoquiones that is 1,4-benzoquinone in which all four hydrogens are substituted by chlorines.	2.57	2	0	1,4-benzoquinones; organochlorine compound	EC 2.7.1.33 (pantothenate kinase) inhibitor; 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
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.	4.8	1	1	aminoglycoside	allergen; antibacterial drug; Escherichia coli metabolite
2,2'-methylenebis(4-methyl-6-tert-butylphenol) [no description available]	2.07	1	0	diarylmethane
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.	4.73	5	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
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.	3.1	1	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.	7.88	30	2	methoxybenzoic acid; monohydroxybenzoic acid	plant metabolite
indolebutyric acid indolebutyric acid: RN given refers to parent cpd. indole-3-butyric acid : A indol-3-yl carboxylic acid that is butanoic acid carrying a 1H-indol-3-yl substituent at position 1.	2.45	2	0	indol-3-yl carboxylic acid	auxin; plant hormone; plant 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
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.	3.53	2	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.	5.33	17	0	alpha,beta-unsaturated monocarboxylic acid; cyclohexenecarboxylic acid; hydroxy monocarboxylic acid	Escherichia coli metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
protocatechualdehyde protocatechualdehyde: found in wheat grains, wheat seedlings, & other plants; RN given refers to parent cpd; see also rancinamycins; structure	2.74	3	0	dihydroxybenzaldehyde
4-tert-octylphenol 4-tert-octylphenol: structure given in first source	7.17	1	0	alkylbenzene
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.	3.06	4	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.	3.53	2	0	medium-chain fatty acid; straight-chain saturated fatty acid	human metabolite; plant metabolite
pregnenolone [no description available]	3.1	1	0	20-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; C21-steroid	human metabolite; mouse metabolite
diphenhydramine hydrochloride Antitussive Agents: Agents that suppress cough. They act centrally on the medullary cough center. EXPECTORANTS, also used in the treatment of cough, act locally.. diphenhydramine hydrochloride : The hydrochloride salt of diphenhydramine.	3.18	5	0	hydrochloride; organoammonium salt	anti-allergic agent; antiemetic; antiparkinson drug; antipruritic drug; H1-receptor antagonist; local anaesthetic; muscarinic antagonist; sedative
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
mequinol mequinol: depigmenting agent; RN given refers to parent cpd	4.31	3	0	methoxybenzenes; phenols	metabolite
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.	13.35	164	8	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
perylene Perylene: A 20-carbon dibenz(de,kl)anthracene that can be viewed as a naphthalene fused to a phenalene or as dinaphthalene. It is used as fluorescent lipid probe in the cytochemistry of membranes and is a polycyclic hydrocarbon pollutant in soil and water. Derivatives may be carcinogenic.. perylene : An ortho- and peri-fused polycyclic arene comprising of five benzene rings that is anthracene in which the d,e and k,l sides are fused to benzene rings.	3.76	10	0	ortho- and peri-fused polycyclic arene; perylenes
benz(a)acridine [no description available]	2.15	1	0	organonitrogen heterocyclic compound; polycyclic heteroarene
benz(c)acridine [no description available]	2.13	1	0	organonitrogen heterocyclic compound; polycyclic heteroarene
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.	2.11	1	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.	3.11	5	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.	4.8	1	1	indazole
benzoxazoles 1,3-benzoxazole : A benzoxazole in which the benzene ring is fused to a 1,3-oxazole ring across positions 4 and 5.. benzoxazole : Compounds based on a fused 1,2- or 1,3-oxazole and benzene bicyclic ring skeleton.	1.99	1	0	1,3-benzoxazoles; mancude organic heterobicyclic parent
azulene [no description available]	2.04	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.	3.31	6	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.	2.05	1	0	isoxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
thiazoles [no description available]	5.42	4	1	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.	2.74	3	0	diazine; pyrazines	Daphnia magna metabolite
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.	3.23	1	0	phenethylamine alkaloid; phenylethanolamines	bacterial metabolite; environmental contaminant; nasal decongestant; plant metabolite; sympathomimetic agent; vasoconstrictor agent; xenobiotic
hydrazine diamine : Any polyamine that contains two amino groups.	5.46	4	1	azane; hydrazines	EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
thiocyanate thiocyanate: RN given refers to parent cpd. thiocyanate : A pseudohalide anion obtained by deprotonation of the thiol group of thiocyanic acid.	2.04	1	0	pseudohalide anion; sulfur molecular entity	human metabolite
monocrotaline Monocrotaline: A pyrrolizidine alkaloid and a toxic plant constituent that poisons livestock and humans through the ingestion of contaminated grains and other foods. The alkaloid causes pulmonary artery hypertension, right ventricular hypertrophy, and pathological changes in the pulmonary vasculature. Significant attenuation of the cardiopulmonary changes are noted after oral magnesium treatment.	7.79	3	0	pyrrolizidine alkaloid
perfluorooctanoic acid perfluorooctanoic acid: RN given refers to parent cpd. perfluorooctanoic acid : A fluoroalkanoic acid that is perfluorinated octanoic acid.	7.31	1	0	fluoroalkanoic acid	carcinogenic agent; endocrine disruptor; environmental contaminant; surfactant; xenobiotic
citrulline citrulline : The parent compound of the citrulline class consisting of ornithine having a carbamoyl group at the N(5)-position.	2.06	1	0	amino acid zwitterion; citrulline	Daphnia magna metabolite; EC 1.14.13.39 (nitric oxide synthase) inhibitor; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; protective agent; Saccharomyces cerevisiae metabolite
4-hydroxyphenobarbital [no description available]	3.1	1	0	barbiturates
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
4-methylcatechol [no description available]	2.48	2	0	methylcatechol	antioxidant; carcinogenic agent; hapten; human metabolite; plant metabolite
hydantoins Hydantoins: Compounds based on imidazolidine dione. Some derivatives are ANTICONVULSANTS.. imidazolidine-2,4-dione : An imidazolidinone with oxo groups at position 2 and 4.	4.8	1	1	imidazolidine-2,4-dione
jervine jervine: teratogen from Veratrum grandiflorum; RN given refers to parent cpd(3beta,23beta)-isomer; structure	2.07	1	0	piperidines
glycyrrhetinic acid [no description available]	2.07	1	0	cyclic terpene ketone; hydroxy monocarboxylic acid; pentacyclic triterpenoid	immunomodulator; plant metabolite
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.	3.85	3	0	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human metabolite; mouse 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.	3.68	9	0
boldine [no description available]	2.54	2	0	aporphine alkaloid
rhein [no description available]	3.65	2	0	dihydroxyanthraquinone
indirubin [no description available]	2.07	1	0
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
plumbagin plumbagin: a superoxide anion generator. plumbagin : A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 2 and 5 are substituted by methyl and hydroxy groups, respectively.	3.93	3	0	hydroxy-1,4-naphthoquinone; phenols	anticoagulant; antineoplastic agent; immunological adjuvant; metabolite
cepharanthine cepharanthine: isoquinoline alkaloid from tubers of STEPHANIA; stimulates recovery of immunologic function in lymphatic system after administration of antineoplastic agents or x-irradiation. cepharanthine : A bisbenzylisoquinoline alkaloid from tubers of Stephania; stimulates recovery of immunologic function in lymphatic system after administration of antineoplastic agents or x-irradiation.	2.07	1	0	bisbenzylisoquinoline alkaloid; isoquinolines
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.	2.07	1	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.	3.1	1	0	dihydroxyanthraquinone	anti-inflammatory agent; antiviral agent; plant metabolite
osthol osthol: from Cnidium monnieri and Angelica pubescens (both Apiaceae); structure given in first source	2.07	1	0	botanical anti-fungal agent; coumarins	metabolite
cytisine [no description available]	2.07	1	0	alkaloid; bridged compound; lactam; organic heterotricyclic compound; secondary amino compound	nicotinic acetylcholine receptor agonist; phytotoxin; plant metabolite
bicuculline Bicuculline: An isoquinoline alkaloid obtained from Dicentra cucullaria and other plants. It is a competitive antagonist for GABA-A receptors.. bicuculline : A benzylisoquinoline alkaloid that is 6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline which is substituted at the 5-pro-S position by a (6R)-8-oxo-6,8-dihydrofuro[3,4-e][1,3]benzodioxol-6-yl group. A light-sensitive competitive antagonist of GABAA receptors. It was originally identified in 1932 in plant alkaloid extracts and has been isolated from Dicentra cucullaria, Adlumia fungosa, Fumariaceae, and several Corydalis species.	2.07	1	0	benzylisoquinoline alkaloid; isoquinoline alkaloid; isoquinolines	agrochemical; central nervous system stimulant; GABA-gated chloride channel antagonist; GABAA receptor antagonist; neurotoxin
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.	2.43	2	0	flavanones
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.	2.07	1	0	dicarboxylic acid; L-proline derivative; non-proteinogenic L-alpha-amino acid; pyrrolidinecarboxylic acid	antinematodal drug; excitatory amino acid agonist
topanol 354 Topanol 354: structure	3.25	1	0	methoxybenzenes; phenols
thymoquinone thymoquinone: constituent of cedarwood; can cause dermatitis; structure. thymoquinone : A member of the class of 1,4-benzoquinones that is 1,4-bezoquinone in which the hydrogens at positions 2 and 5 are replaced by methyl and isopropyl groups, respectively. It is a natural compound isolated from Nigella sativa which has demonstrated promising chemotherapeutic activity.	3.63	2	0	1,4-benzoquinones	adjuvant; anti-inflammatory agent; antidepressant; antineoplastic agent; antioxidant; cardioprotective agent; plant metabolite
capillin capillin: insecticidal principle of Artemisia nilagirica Clarke	3.35	1	0	aromatic ketone; ynone
dithiol dithiol: structure	2.31	1	0
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).	4.06	2	0	botanical anti-fungal agent; p-menthane monoterpenoid; phenols	agrochemical; antimicrobial agent; flavouring agent; TRPA1 channel agonist; volatile oil component
3-pyridinaldehyde pyridine-3-carbaldehyde : A pyridinecarbaldehyde that is pyridine substituted by a formyl group at position 3.	2.11	1	0	pyridinecarbaldehyde
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.	2.47	2	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.	2.78	3	0	hydroxy monocarboxylic acid	plant metabolite
azomethane azomethane: structure	3.1	1	0
isovaleric acid isovaleric acid: structure. isovaleric acid : A C5, branched-chain saturated fatty acid.	2.05	1	0	branched-chain saturated fatty acid; methylbutyric acid; short-chain fatty acid	mammalian metabolite; plant metabolite
margaric acid margaric acid: RN given refers to unlabeled parent cpd. heptadecanoic acid : A C17 saturated fatty acid and trace component of fats in ruminants.	2.05	1	0	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; mammalian metabolite
arachidic acid icosanoic acid : A C20 striaght-chain saturated fatty acid which forms a minor constituent of peanut (L. arachis) and corn oils. Used as an organic thin film in the production of liquid crystals for a wide variety of technical applications.	2.05	1	0	long-chain fatty acid; straight-chain saturated fatty acid	plant metabolite
oleanolic acid [no description available]	3.95	12	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	plant metabolite
dihydroergotamine Dihydroergotamine: A 9,10alpha-dihydro derivative of ERGOTAMINE. It is used as a vasoconstrictor, specifically for the therapy of MIGRAINE DISORDERS.. dihydroergotamine : Ergotamine in which a single bond replaces the double bond between positions 9 and 10. A semisynthetic ergot alkaloid with weaker oxytocic and vasoconstrictor properties than ergotamine, it is used (as the methanesulfonic or tartaric acid salts) for the treatment of migraine and orthostatic hypotension.	2.31	1	0	ergot alkaloid; semisynthetic derivative	dopamine agonist; non-narcotic analgesic; serotonergic agonist; sympatholytic agent; vasoconstrictor agent
abietic acid abietic acid : An abietane diterpenoid that is abieta-7,13-diene substituted by a carboxy group at position 18.	2.47	2	0	abietane diterpenoid; monocarboxylic acid	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.	2.44	2	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.	4.14	14	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.	3.1	1	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.	2.43	2	0
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.	3.45	7	0	flavones	metabolite; nematicide
2,4,6-trimethylphenol [no description available]	3.25	1	0	hydroxytoluene
azomycin azomycin: RN given refers to parent cpd with specified locant; structure	2.07	1	0	C-nitro compound; imidazoles	antitubercular agent
chamazulene chamazulene: structure	2.08	1	0	sesquiterpenoid
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.	5.09	12	0	benzoic acids; dimethoxybenzene; phenols	plant metabolite
herniarin herniarin: methoxy analog of umbelliferone; structure. herniarin : A member of the class of coumarins that is coumarin substituted by a methoxy group at position 7.	2.47	2	0	coumarins	fluorochrome
6-methoxybenzoxazolinone 6-methoxybenzoxazolinone: plant derivative which stimulates reproduction in Microtus montanus. 6-methoxy-2-benzoxazolinone : A 2-benzoxazolinone that is substituted by a methoxy group at position 6.	1.99	1	0	aromatic ether; benzoxazole	antibacterial agent; anticonvulsant; antifungal agent; muscle relaxant; plant metabolite
hydroxyhydroquinone benzene-1,2,4-triol : A benzenetriol carrying hydroxy groups at positions 1, 2 and 4.	5.47	5	3	benzenetriol	mouse metabolite
4-iodophenol [no description available]	3.1	1	0	iodophenol
2,2,4-trimethylpentane 2,2,4-trimethylpentane: nephrotoxic. isooctane : An alkane that consists of pentane bearing two methyl substituents at position 2 and a single methyl substituent at position 4.	2.02	1	0	alkane; volatile organic compound	fuel additive; nephrotoxin; non-polar solvent
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.	5.8	31	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.	7.83	3	0	arenesulfonic acid; C-nitro compound	epitope; explosive; reagent
1-naphthylisothiocyanate 1-Naphthylisothiocyanate: A tool for the study of liver damage which causes bile stasis and hyperbilirubinemia acutely and bile duct hyperplasia and biliary cirrhosis chronically, with changes in hepatocyte function. It may cause skin and kidney damage.	2.46	2	0	isothiocyanate	insecticide
lignoceric acid lignoceric acid: RN given refers to parent cpd; structure. tetracosanoic acid : A C24 straight-chain saturated fatty acid.	2.05	1	0	straight-chain saturated fatty acid; very long-chain fatty acid	Daphnia tenebrosa metabolite; human metabolite; plant metabolite; volatile oil component
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.	3.1	1	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.	2.05	1	0	2-hydroxy monocarboxylic acid; hydroxybutyric acid	algal metabolite; human metabolite
3-hydroxyflavone 3-hydroxyflavone: structure given in first source. flavonol : A monohydroxyflavone that is the 3-hydroxy derivative of flavone.	7.25	28	1	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
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
1-methylcyclopropane 1-methylcyclopropane: do not confuse with MCP cpd (1-methylcyclopropene)	2.03	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
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).	3.1	1	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]	2.08	1	0	hexitol	Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite
n-methyl-n-nitrosoaniline N-methyl-N-nitrosoaniline: structure	6.95	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.	4.25	5	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
4-(dimethylamino)benzoic acid [no description available]	2.31	1	0
5-methyl-2-furfural 5-methyl-2-furfural: RN given refers to cpd with locants as specified	2.54	2	0	aldehyde; furans	EC 2.2.1.6 (acetolactate synthase) inhibitor; flavouring agent; human metabolite; Maillard reaction product
4,4'-bisphenol f 4,4'-bisphenol F: RN given refers to parent cpd. bisphenol F : A bisphenol that is methane in which two of the hydrogens have been replaced by 4-hydroxyphenyl groups.	2.08	1	0	bisphenol; diarylmethane	environmental food contaminant; xenoestrogen
Berberine chloride (TN) [no description available]	3.6	2	0	organic molecular entity
tridecanoic acid tridecanoate : A long-chain fatty acid anion resulting from the removal of a proton from the carboxy group of tridecanoic acid.. tridecanoic acid : A C13 straight-chain saturated fatty acid.	2.05	1	0	long-chain fatty acid; straight-chain saturated fatty acid	plant metabolite
isovanillic acid 3-hydroxy-4-methoxybenzoic acid : A methoxybenzoic acid that is 4-methoxybenzoic acid bearing a hydroxy substituent at position 3.	2.44	2	0	methoxybenzoic acid; monohydroxybenzoic acid	antibacterial agent; plant metabolite
4-propylphenol 4-propylphenol: structure given in first source	3.1	1	0	alkylbenzene
nonadecanoic acid nonadecanoic acid : A C19 straight-chain fatty acid of plant or bacterial origin. An intermediate in the biodegradation of n-icosane, it has been shown to inhibit cancer growth.	2.05	1	0	long-chain fatty acid; straight-chain saturated fatty acid	fungal metabolite
mannoheptulose Mannoheptulose: A 7-carbon keto sugar having the mannose configuration.. D-keto-manno-heptulose : The open chain form of D-manno-heptulose.. D-manno-heptulose : A manno-heptulose with a D-configuration. It has been found in avocados.	2.6	1	0	D-manno-heptulose
agaric acid agaric acid: adenine nucleotide translocase antagonist	2.31	1	0
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.	2	1	0	N-nitrosoureas	alkylating agent; carcinogenic agent; mutagen; teratogenic agent
levonorgestrel Levonorgestrel: A synthetic progestational hormone with actions similar to those of PROGESTERONE and about twice as potent as its racemic or (+-)-isomer (NORGESTREL). It is used for contraception, control of menstrual disorders, and treatment of endometriosis.	4.8	1	1	17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; terminal acetylenic compound	contraceptive drug; female contraceptive drug; progestin; synthetic oral contraceptive
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.	2.15	1	0	gallate ester	plant metabolite
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.	8.55	2	0	organofluorine compound; secondary alcohol	drug metabolite
1-methylpyridinium 1-methylpyridinium: RN given refers to parent cpd	7.81	11	4	methylpyridines
deoxycytidine [no description available]	2.15	1	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
chlormequat Chlormequat: A plant growth regulator that is commonly used on ornamental plants.. chlormequat : A quaternary ammonium ion that is choline in which the hydroxy group has been replaced by a chlorine. Its salts (particularly the chloride salt, known as chlormequat chloride) are used as plant growth retardants.	2.1	1	0	quaternary ammonium ion	plant growth retardant
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.	3.85	2	1	guaiacols; monocarboxylic acid; phenylpropanoid	antioxidant; human xenobiotic metabolite; mouse metabolite; plant metabolite
calcium peroxide [no description available]	4.8	1	1	calcium oxides
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).	2.96	3	0
cadmium sulfide [no description available]	2.15	1	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)	2.46	2	0	alkali metal hydroxide
manganese dioxide [no description available]	4.8	1	1	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.	5.14	2	1	zinc molecular entity
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.	7.25	1	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.	4.36	7	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	23	1	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]	2.78	3	0
vincamine Vincamine: A major alkaloid of Vinca minor L., Apocynaceae. It has been used therapeutically as a vasodilator and antihypertensive agent, particularly in cerebrovascular disorders.	2.07	1	0	alkaloid ester; hemiaminal; methyl ester; organic heteropentacyclic compound; vinca alkaloid	antihypertensive agent; metabolite; vasodilator agent
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
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.	2.97	4	0	organic cation	geroprotector; herbicide
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.	2.46	2	0	hydroquinones	food antioxidant
guanoxan guanoxan: was MH 1976-92 (see under GUANIDINES 1976-90); use GUANIDINES to search GUANOXAN 1976-92; antihypertensive agent similar in its mechanism of action to guanethidine; may cause liver damage	2.07	1	0	benzodioxine
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
phenethyl isothiocyanate phenethyl isothiocyanate: a dietary liver aldehyde dehydrogenase inhibitor; promotes urinary bladder carcinoma. phenethyl isothiocyanate : An isothiocyanate having a phenethyl group attached to the nitrogen. It is a naturally occurring compound found in some cruciferous vegetables (e.g. watercress) and is known to possess anticancer properties.	2.31	1	0	isothiocyanate	antineoplastic agent; EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor; metabolite
muscarine [no description available]	2.07	1	0
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.	2.02	1	0	2-benzofurans; gamma-lactone; organic heteropentacyclic compound; oxaspiro compound; polyphenol; xanthene dye	fluorescent dye; radioopaque medium
heneicosanoic acid henicosanoic acid : A long-chain fatty acid that is henicosane in which one of the methyl groups has been oxidised to give the corresponding carboxylic acid.	2.05	1	0	long-chain fatty acid; straight-chain saturated fatty acid
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.	2.15	1	0	organic chloride salt	fluorochrome; geroprotector; histological dye
tricosanoic acid tricosanoic acid : A very long-chain fatty acid that is tricosane in which one of the methyl groups has been oxidised to the corresponding carboxylic acid.	2.05	1	0	straight-chain saturated fatty acid; very long-chain fatty acid	Daphnia magna metabolite; human metabolite; plant metabolite
1,2-benzisothiazoline-3-one 1,2-benzisothiazoline-3-one: a preservative in water-based solutions such as paints, cutting fluids, printing inks, cleaning agents, polyvinyl chloride gloves, etc.. benzo[d]isothiazol-3-one : An organic heterobicyclic compound based on a fused 1,2-thiazole and benzene bicyclic ring skeleton, with the S atom positioned adjacent to one of the positions of ring fusion.	2.31	1	0	organic heterobicyclic compound; organonitrogen heterocyclic compound	disinfectant; drug allergen; environmental contaminant; platelet aggregation inhibitor; sensitiser; xenobiotic
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
methyl methanethiosulfonate S-methyl methanethiosulfonate : A sulfonic acid derivative obtained by condensaton of methanesulfonic acid with methanethiol.	1.99	1	0	sulfonic acid derivative; thiosulfonate ester	metabolite
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.	2.53	2	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.	2.43	2	0	thujene	plant metabolite
mannose mannopyranose : The pyranose form of mannose.	2.02	1	0	D-aldohexose; D-mannose; mannopyranose	metabolite
palmatine burasaine: structure in first source	2.1	1	0	berberine alkaloid; organic heterotetracyclic compound	plant metabolite
ecdysone [no description available]	2.07	1	0	14alpha-hydroxy steroid; 22-hydroxy steroid; 25-hydroxy steroid; 2beta-hydroxy steroid; 3beta-sterol; 6-oxo steroid; ecdysteroid	prohormone
streptomycin [no description available]	2.43	2	0	antibiotic antifungal drug; antibiotic fungicide; streptomycins	antibacterial drug; antifungal agrochemical; antimicrobial agent; antimicrobial drug; bacterial metabolite; protein synthesis inhibitor
pentaethylenehexamine [no description available]	2	1	0
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
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
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.	4.21	2	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.	2.83	3	0	amino dicarboxylic acid; D-alpha-amino acid; D-aspartic acid derivative; secondary amino compound	neurotransmitter agent
ammonium nitrate ammonium nitrate: structure. ammonium nitrate : The ammonium salt of nitric acid.	2.01	1	0	ammonium salt; inorganic molecular entity; inorganic nitrate salt	explosive; fertilizer; oxidising agent
psoromic acid psoromic acid: structure in first source	1.99	1	0	carbonyl compound
n-deacetyl-n-formylcolchicine N-deacetyl-N-formylcolchicine: structure given in first source	2.07	1	0	cyclic ketone
iridium Iridium: A metallic element with the atomic symbol Ir, atomic number 77, and atomic weight 192.22.	7.05	1	0	cobalt group element atom; platinum group metal 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.	5.42	4	1	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.	4.8	1	1	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.	5.05	2	1	chromium group element atom	micronutrient
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.	2.25	1	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.	7.41	1	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.	5.8	6	1	copper group element atom; elemental silver	Escherichia coli metabolite
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.	5.3	2	1	titanium group element atom
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.	3.3	5	0	cadmium molecular entity; zinc group element 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.	2.46	2	0	chromium group element atom; metal allergen	micronutrient
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.	7.17	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.	5.98	7	1	copper group element atom; elemental gold
zirconium Zirconium: A rather rare metallic element with atomic number 40, atomic weight 91.224, and symbol Zr.	3.06	4	0	titanium group element atom
aluminum chloride Aluminum Chloride: A compound with the chemical formula AlCl3; the anhydrous salt is used as a catalyst in organic chemical synthesis, and hydrated salts are used topically as antiperspirants, and for the management of HYPERHYDROSIS.	3.06	4	0	aluminium coordination entity	Lewis acid
galactosamine 2-amino-2-deoxy-D-galactopyranose : The pyranose form of D-galactosamine.. D-galactosamine : The D-stereoisomer of galactosamine.	5.47	4	1	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.	8.14	5	0	chlorine oxoacid; reactive oxygen species	EC 2.5.1.18 (glutathione transferase) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; human metabolite
camptothecin NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source	2.07	1	0	delta-lactone; pyranoindolizinoquinoline; quinoline alkaloid; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor; genotoxin; plant metabolite
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.	2.02	1	0	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.	2.02	1	0	diatomic bromine
potassium persulfate [no description available]	2.15	1	0
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.	4.8	1	1	metal sulfate; zinc molecular entity	fertilizer
potassium nitrate potassium nitrate: RN given refers to cpd with MF of K-HNO3; when combined with charcoal and sulfur it can form EXPLOSIVE AGENTS. potassium nitrate : The inorganic nitrate salt of potassium.	2.01	1	0	inorganic nitrate salt; potassium salt	fertilizer
sodium sulfate [no description available]	7.6	1	0	inorganic sodium salt
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.	5.14	2	1	calcium phosphate
silver nitrate Silver Nitrate: A silver salt with powerful germicidal activity. It has been used topically to prevent OPHTHALMIA NEONATORUM.	1.94	1	0	inorganic nitrate salt; silver salt	astringent
chlorine Chlorine: An element with atomic symbol Cl, atomic number 17, and atomic weight 35, and member of the halogen family.	2.77	3	0	diatomic chlorine; gas molecular entity	bleaching agent
nitrous acid Nitrous Acid: Nitrous acid (HNO2). A weak acid that exists only in solution. It can form water-soluble nitrites and stable esters. (From Merck Index, 11th ed)	2.04	1	0	nitrogen oxoacid
butylated hydroxyanisole [no description available]	3.1	1	0
galactose aldohexose : A hexose with a (potential) aldehyde group at one end.	2.17	1	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.	2.43	2	0	elemental molecule; gas molecular entity; reactive oxygen species; triatomic oxygen	antiseptic drug; disinfectant; electrophilic reagent; greenhouse gas; mutagen; oxidising agent; tracer
ammonium ferric sulfate ammonium ferrous sulfate: supplies nutritional iron. ferrous ammonium sulfate (anhydrous) : A compound of ammonium, iron and sulfate in which the ratio of ammonium to iron(2+) to sulfate ions is 2:1:2.	2	1	0	ammonium salt; iron molecular entity; metal sulfate	ferroptosis inducer
sodium selenite disodium selenite : An inorganic sodium salt composed of sodium and selenite ions in a 2:1 ratio.	2.08	1	0	inorganic sodium salt; selenite salt	nutraceutical
4-chloro-7-nitrobenzofurazan 4-Chloro-7-nitrobenzofurazan: A benzofuran derivative used as a protein reagent since the terminal N-NBD-protein conjugate possesses interesting fluorescence and spectral properties. It has also been used as a covalent inhibitor of both beef heart mitochondrial ATPase and bacterial ATPase.. 4-chloro-7-nitrobenzofurazan : A benzoxadiazole that is 2,1,3-benzoxadiazole which is substituted at position 4 by chlorine and at position 7 by a nitro group.	2.04	1	0	benzoxadiazole; C-nitro compound; organochlorine compound	EC 1.4.3.4 (monoamine oxidase) inhibitor; EC 3.6.1.3 (adenosinetriphosphatase) inhibitor; fluorescent probe; fluorochrome
cadmium nitrate cadmium nitrate: RN given refers to parent cpd. cadmium nitrate : An inorganic nitrate salt having Cd(2+) as the counterion.	2.15	1	0	cadmium salt; inorganic nitrate salt	carcinogenic agent; genotoxin; hepatotoxic agent
chloramine [no description available]	7	1	0	halide
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.	2.44	2	0	ammonium salt; inorganic chloride	ferroptosis inhibitor
ethionine L-ethionine : An S-ethylhomocysteine that has S-configuration at the chiral centre.	2.02	1	0	S-ethylhomocysteine	antimetabolite; carcinogenic agent
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.	4.8	1	1	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.	2.03	1	0
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.	3.8	1	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
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.	3.8	11	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
fluorides [no description available]	1.94	1	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
stannic oxide tin dioxide : A tin oxide compound consisting of tin(IV) covalently bound to two oxygen atoms.	2.25	1	0	tin oxide
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.	2.11	1	0	anthocyanin chlorides
1-deoxynojirimycin 1-deoxy-nojirimycin: structure in first source. duvoglustat : An optically active form of 2-(hydroxymethyl)piperidine-3,4,5-triol having 2R,3R,4R,5S-configuration.	2.13	1	0	2-(hydroxymethyl)piperidine-3,4,5-triol; piperidine alkaloid	anti-HIV agent; anti-obesity agent; bacterial metabolite; EC 3.2.1.20 (alpha-glucosidase) inhibitor; hepatoprotective agent; hypoglycemic agent; plant metabolite
iodine [no description available]	2.21	1	0	halide anion; monoatomic iodine	human metabolite
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.	3.1	1	0	aminoglycoside antibiotic; anthracycline; p-quinones; tetracenequinones	antineoplastic agent; bacterial metabolite
2-bromoergocryptine mesylate [no description available]	2.07	1	0	methanesulfonate salt	antiparkinson drug
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.	2.07	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.	3.65	9	0	benzenes; phenyl acetates
n-phenylethanolamine [no description available]	3.1	1	0	aralkylamine
cetylpyridinium chloride anhydrous tserigel: according to first source contains polyvinylbutyral & cetylpyridinium chloride; UD only lists cetylpyridinium chloride as constituent. cetylpyridinium chloride : A pyridinium salt that has N-hexadecylpyridinium as the cation and chloride as the anion. It has antiseptic properties and is used in solutions or lozenges for the treatment of minor infections of the mouth and throat.	6.79	5	0	chloride salt; organic chloride salt	antiseptic drug; surfactant
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.	3.1	1	0	phenols	fungal xenobiotic metabolite
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.	3.53	2	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.	4.58	4	0	phenols	antioxidant; ferroptosis inhibitor; food additive; geroprotector
1,4,5,8-naphthalenetetracarboxylic acid 1,4,5,8-naphthalenetetracarboxylic acid: structure given in first source	1.99	1	0
silybin silibinin : A flavonolignan isolated from milk thistle, Silybum marianum, that has been shown to exhibit antioxidant and antineoplastic activities.	2.25	1	0	aromatic ether; benzodioxine; flavonolignan; polyphenol; secondary alpha-hydroxy ketone	antineoplastic agent; antioxidant; hepatoprotective agent; plant metabolite
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.	2.15	1	0
alkenes [no description available]	2.07	1	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).	2.1	1	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.	3.83	10	0	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
azoxymethane Azoxymethane: A potent carcinogen and neurotoxic compound. It is particularly effective in inducing colon carcinomas.	7.94	4	0
azides Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.	2	1	0	pseudohalide anion	mitochondrial respiratory-chain inhibitor
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.	3.56	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.	2.08	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).	4.18	4	0	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
etoposide [no description available]	2.07	1	0	beta-D-glucoside; furonaphthodioxole; organic heterotetracyclic compound	antineoplastic agent; DNA synthesis inhibitor
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
ribavirin Rebetron: Rebetron is tradename	3.38	2	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
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.	2.07	1	0	butyrate ester; phorbol ester; tertiary alpha-hydroxy ketone
cephradine Cephradine: A semi-synthetic cephalosporin antibiotic.. cephradine : A first-generation cephalosporin antibiotic with a methyl substituent at position 3, and a (2R)-2-amino-2-cyclohexa-1,4-dien-1-ylacetamido substituent at position 7, of the cephem skeleton.	2.07	1	0	beta-lactam antibiotic allergen; cephalosporin	antibacterial drug
imidazolidinyl urea imidazolidinyl urea: RN given refers to parent cpd	2	1	0	ureas	antimicrobial 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.	2.15	1	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
deoxynivalenol deoxynivalenol : A trichothecene mycotoxin produced by Fusarium to which wheat, barley, maize (corn) and their products are susceptible to contamination.	7.82	3	0	cyclic ketone; enone; primary alcohol; secondary alpha-hydroxy ketone; trichothecene; triol	mycotoxin
quisqualic acid Quisqualic Acid: An agonist at two subsets of excitatory amino acid receptors, ionotropic receptors that directly control membrane channels and metabotropic receptors that indirectly mediate calcium mobilization from intracellular stores. The compound is obtained from the seeds and fruit of Quisqualis chinensis.	2.07	1	0	non-proteinogenic alpha-amino acid
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid [no description available]	5.16	14	0	chromanol; monocarboxylic acid; phenols	antioxidant; ferroptosis inhibitor; neuroprotective agent; radical scavenger; Wnt signalling inhibitor
nitazoxanide nitazoxanide: a 5-nitrothiazolyl derivative used for a broad range of intestinal parasitic infections including CRYPTOSPORIDIUM and GIARDIA; it is a redox-active nitrothiazolyl-salicylamide prodrug	2.6	1	0	benzamides; carboxylic ester
acarbose [no description available]	2.61	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
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.	2.41	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.	2.25	1	0	alkanethiol; L-proline derivative; N-acylpyrrolidine; pyrrolidinemonocarboxylic acid	antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor
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.	2.07	1	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
fenoldopam mesylate [no description available]	2.25	1	0	benzazepine
1-octanesulfonic acid 1-octanesulfonic acid: RN given refers to parent cpd	2.11	1	0	organosulfonic acid	local anaesthetic
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
swainsonine Swainsonine: An indolizidine alkaloid from the plant Swainsona canescens that is a potent alpha-mannosidase inhibitor. Swainsonine also exhibits antimetastatic, antiproliferative, and immunomodulatory activity.. swainsonine : An indolizidine alkaloid isolated from the plant Swainsona canescens with three hydroxy substituents at positions 1, 2 and 8.	2.07	1	0	indolizidine alkaloid	antineoplastic agent; EC 3.2.1.114 (mannosyl-oligosaccharide 1,3-1,6-alpha-mannosidase) inhibitor; immunological adjuvant; plant metabolite
castanospermine castanospermine: indolizidine alkaloid from seeds of Australian legume, Castanospermum australe. castanospermine : A tetrahydroxyindolizidine alkaloid that consists of octahydroindolizine having four hydroxy substituents located at positions 1, 6, 7 and 8 (the 1S,6S,7R,8R,8aR-diastereomer).	2.07	1	0	indolizidine alkaloid	anti-HIV-1 agent; anti-inflammatory agent; EC 3.2.1.* (glycosidase) inhibitor; metabolite
simvastatin Simvastatin: A derivative of LOVASTATIN and potent competitive inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A reductase (HYDROXYMETHYLGLUTARYL COA REDUCTASES), which is the rate-limiting enzyme in cholesterol biosynthesis. It may also interfere with steroid hormone production. Due to the induction of hepatic LDL RECEPTORS, it increases breakdown of LDL CHOLESTEROL.. simvastatin : A member of the class of hexahydronaphthalenes that is lovastatin in which the 2-methylbutyrate ester moiety has been replaced by a 2,2-dimethylbutyrate ester group. It is used as a cholesterol-lowering and anti-cardiovascular disease drug.	3.21	4	0	delta-lactone; fatty acid ester; hexahydronaphthalenes; statin (semi-synthetic)	EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor; EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor; ferroptosis inducer; geroprotector; prodrug
salmeterol xinafoate Salmeterol Xinafoate: A selective ADRENERGIC BETA-2 RECEPTOR agonist that functions as a BRONCHODILATOR when administered by inhalation. It is used to manage the symptoms of ASTHMA and CHRONIC OBSTRUCTIVE PULMONARY DISEASE.	4.8	1	1	naphthoic acid
mibefradil Mibefradil: A benzimidazoyl-substituted tetraline that selectively binds and inhibits CALCIUM CHANNELS, T-TYPE.	2.07	1	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.	2.15	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]	7.52	2	0	aromatic amide; dihydroxy monocarboxylic acid; monofluorobenzenes; pyrroles; statin (synthetic)	environmental contaminant; xenobiotic
adenosine quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit	10.65	5	1	adenosines; purines D-ribonucleoside	analgesic; anti-arrhythmia drug; fundamental metabolite; human metabolite; vasodilator agent
octyl gallate [no description available]	3.1	1	0	gallate ester	food antioxidant; hypoglycemic agent; plant metabolite
pyranine pyranine: structure	2.17	1	0	organic sodium salt	fluorochrome
nitrogen trioxide [no description available]	7.03	1	0	nitrogen oxide
zinc ethylphenyldithiocarbamate [no description available]	2.31	1	0
zircon zircon: RN given refers to Zr(+4)[1:1] salt; structure	2.1	1	0
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.	2.45	2	0	6-aminopurines	cytokinin; plant metabolite
cuprous chloride cuprous chloride: RN given refers to unlabeled cpd. copper(I) chloride : An inorganic chloride of copper in which the metal is in the +1 oxidation state.	2.01	1	0	copper molecular entity; inorganic chloride	agrochemical; molluscicide
daunorubicin hydrochloride [no description available]	2.07	1	0	anthracycline
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
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.	4.24	5	0	hydrochloride	adrenergic antagonist; antidepressant; H1-receptor antagonist; sedative; serotonin uptake inhibitor
4-[1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol [no description available]	3.1	1	0	stilbenoid
3,4,5,3',4'-pentachlorobiphenyl 3,3',4,4',5-pentachlorobiphenyl : A pentachlorobiphenyl in which the chlorines are located at the 3, 4, 5, 3', and 4' positions.	2.13	1	0	pentachlorobiphenyl; trichlorobenzene
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.	10.07	120	2	D-glucopyranose	epitope; mouse metabolite
mevastatin mevastatin: antifungal metabolite from Penicillium brevicopactum; potent inhibitory activity to sterol synthesis; structure. mevastatin : A carboxylic ester that is pravastatin that is lacking the allylic hydroxy group. A hydroxymethylglutaryl-CoA reductase inhibitor (statin) isolated from Penicillium citrinum and from Penicillium brevicompactum, its clinical use as a lipid-regulating drug ceased following reports of toxicity in animals.	2.07	1	0	2-pyranones; carboxylic ester; hexahydronaphthalenes; polyketide; statin (naturally occurring)	antifungal agent; apoptosis inducer; EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor; fungal metabolite; Penicillium metabolite
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.	2.08	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]	3.49	7	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	geroprotector; plant metabolite
norharman norharman: RN given refers to parent cpd. beta-carboline : The parent compound of the beta-carbolines, a tricyclic structure comprising an indole ring system ortho- fused to C-3 and C-4 of a pyridine ring.	2.07	1	0	beta-carbolines; mancude organic heterotricyclic parent	fungal metabolite; marine metabolite
betulinic acid [no description available]	2.54	2	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
arctigenin arctigenin: precursor to catechols; in many plants	2.78	3	0	lignan
baicalin [no description available]	5.83	34	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
oseltamivir Oseltamivir: An acetamido cyclohexene that is a structural homolog of SIALIC ACID and inhibits NEURAMINIDASE.. oseltamivir : A cyclohexenecarboxylate ester that is the ethyl ester of oseltamivir acid. An antiviral prodrug (it is hydrolysed to the active free carboxylic acid in the liver), it is used to slow the spread of influenza.	2.5	2	0	acetamides; amino acid ester; cyclohexenecarboxylate ester; primary amino compound	antiviral drug; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor; environmental contaminant; prodrug; xenobiotic
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.	6.47	30	0	flavans; gallate ester; polyphenol	antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite
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.	2.82	3	0	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	1.96	1	0
metaperiodate Periodic Acid: A strong oxidizing agent.	2.38	2	0	iodine oxoacid
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.	2.61	2	0	gallate ester; galloyl beta-D-glucose	anti-inflammatory agent; antineoplastic agent; geroprotector; hepatoprotective agent; plant metabolite; radiation protective agent; radical scavenger
peroxynitric acid [no description available]	2.91	4	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.	2.15	1	0	glutathione derivative; organic disulfide	Escherichia coli metabolite; mouse metabolite
baccatin iii [no description available]	2.07	1	0	acetate ester; benzoate ester; tetracyclic diterpenoid	plant metabolite
secoisolariciresinol secoisolariciresinol: RN given refers to ((R-(R,R))-isomer); RN for cpd without isomeric designation not available 8/89; precursor of lignans found in human urine; structure given in first source. secoisolariciresinol : A lignan that is butane-1,4-diol in which the 2 and 3 positions are substituted by 4-hydroxy-3-methoxybenzyl groups. (-)-secoisolariciresinol : An enantiomer of secoisolariciresinol having (-)-(2R,3R)-configuration.	2.11	1	0	secoisolariciresinol	antidepressant; phytoestrogen; plant metabolite
taleranol taleranol: a metabolite of ZEARALENONE which is a non-steroidal estrogenic lactone used as an anabolic compound in animal feed; a stereoisomer of ZERANOL (alpha-zearalanol)	2.07	1	0	macrolide
narasin [no description available]	2.07	1	0	diterpene glycoside
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
quassin quassin: article discusses quassinoid principle; structure	2.07	1	0	triterpenoid
tomatidine tomatidine: RN given refers to (3beta,5alpha,22beta,25S)-isomer; structure. tomatidine : A 3beta-hydroxy steroid resulting from the substitution of the 3beta-hydrogen of tomatidane by a hydroxy group.	2.07	1	0	3beta-hydroxy steroid; azaspiro compound; oxaspiro compound
aloxistatin aloxistatin: a membrane-permeable cysteine protease inhibitor. aloxistatin : An L-leucine derivative that is the amide obtained by formal condensation of the carboxy group of (2S,3S)-3-(ethoxycarbonyl)oxirane-2-carboxylic acid with the amino group of N-(3-methylbutyl)-L-leucinamide.	2.07	1	0	epoxide; ethyl ester; L-leucine derivative; monocarboxylic acid amide	anticoronaviral agent; cathepsin B inhibitor
physodic acid physodic acid: lichen constituent	1.99	1	0	carbonyl compound
rutecarpine rutacarpine: from Evodia rutaecarpa; an ingredient in zhuyu hewei zhitong capsules	2.07	1	0	beta-carbolines
telmisartan Telmisartan: A biphenyl compound and benzimidazole derivative that acts as an angiotensin II type 1 receptor antagonist. It is used in the management of HYPERTENSION.. telmisartan : A member of the class of benzimidazoles used widely in the treatment of hypertension.	7.21	1	0	benzimidazoles; biphenyls; carboxybiphenyl	angiotensin receptor antagonist; antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; environmental contaminant; xenobiotic
bergenin bergenin: RN refers to (2R-(2alpha,3beta,4alpha,4aalpha,10bbeta))-isomer; structure	7.49	2	0	trihydroxybenzoic acid	metabolite
allyl methyl sulfide [no description available]	2.02	1	0	organic sulfide
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
thiochrome thiochrome: structure	1.96	1	0
5-nitrosalicylaldehyde [no description available]	2.4	2	0
5,5'-methylenedisalicylic acid 5,5'-methylenedisalicylic acid: inhibits attachment of ribosomes to microsomal membranes; RN given refers to parent cpd; structure in first source & Merck Index, 9th ed, #5934	1.99	1	0
n-acetyl-l-arginine N-acetyl-L-arginine: has effect on convulsive seizures. N(alpha)-acetyl-L-arginine : An N-acetyl-L-amino acid that is L-arginine in which one of the hydrogens attached to the nitrogen is replaced by an acetyl group.	2.01	1	0	N-acetyl-L-amino acid	human metabolite
1,7-phenanthroline [no description available]	2.05	1	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.	2.41	2	0	1,2,3-triazole
atranorin atranorin: RN given refers to parent cpd; structure given in first source	1.99	1	0	carbonyl compound
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.	2.07	1	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.	2.17	1	0	aromatic ketone; benzenetriol; methyl ketone	MALDI matrix material; plant metabolite
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.	2.52	2	0	isocoumarins
5-hydroxyflavone [no description available]	2.52	2	0	flavones
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
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
fluorodeoxyglucose f18 Fluorodeoxyglucose F18: The compound is given by intravenous injection to do POSITRON-EMISSION TOMOGRAPHY for the assessment of cerebral and myocardial glucose metabolism in various physiological or pathological states including stroke and myocardial ischemia. It is also employed for the detection of malignant tumors including those of the brain, liver, and thyroid gland. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1162)	4.8	1	1	2-deoxy-2-((18)F)fluoro-D-glucose; 2-deoxy-2-fluoro-aldehydo-D-glucose
talinolol [no description available]	2.07	1	0	ureas
artemisinin (+)-artemisinin : A sesquiterpene lactone obtained from sweet wormwood, Artemisia annua, which is used as an antimalarial for the treatment of multi-drug resistant strains of falciparum malaria.	8.65	2	0	organic peroxide; sesquiterpene lactone	antimalarial; plant metabolite
artemether Artemether: An artemisinin derivative that is used in the treatment of MALARIA.. artemether : An artemisinin derivative that is artemisinin in which the lactone has been converted to the corresponding lactol methyl ether. It is used in combination with lumefantrine as an antimalarial for the treatment of multi-drug resistant strains of falciparum malaria.	3.35	1	0	artemisinin derivative; cyclic acetal; organic peroxide; semisynthetic derivative; sesquiterpenoid	antimalarial
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
4-benzoylbenzoic acid 4-carboxybenzophenone: a photosensitizer agent	2.17	1	0
beta-hydroxyisovaleric acid 3-hydroxyisovaleric acid : A 3-hydroxy monocarboxylic acid that is isovaleric acid substituted at position 3 by a hydroxy group. Used as indicator of biotin deficiency.	2.1	1	0	3-hydroxy monocarboxylic acid	human metabolite
2-hydroxy-4-methoxybenzaldehyde 2-hydroxy-4-methoxybenzaldehyde: from African medicinal plants: Mondia whitei (Apocynaceae), Rhus vulagaris (Anacardiaceae), Sclerocarya caffra (Anacardiaceae)	2.11	1	0	methoxybenzenes; phenols
2,3-diaminonaphthalene [no description available]	2.41	2	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.	2.07	1	0	aromatic ether; hydroxycoumarin	plant metabolite
2-hydroxychavicol 2-hydroxychavicol: antimutagen from betel leaf; structure given in first source	2.07	1	0
vinburnine [no description available]	2.07	1	0	alkaloid
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.	2.49	2	0
voriconazole Voriconazole: A triazole antifungal agent that specifically inhibits STEROL 14-ALPHA-DEMETHYLASE and CYTOCHROME P-450 CYP3A.. voriconazole : A triazole-based antifungal agent used for the treatment of esophageal candidiasis, invasive pulmonary aspergillosis, and serious fungal infections caused by Scedosporium apiospermum and Fusarium spp. It is an inhibitor of cytochrome P450 2C9 (CYP2C9) and CYP3A4.	2.17	1	0	conazole antifungal drug; difluorobenzene; pyrimidines; tertiary alcohol; triazole antifungal drug	P450 inhibitor
vanitiolide [no description available]	2.31	1	0	methoxybenzenes; phenols
epicatechin (-)-epicatechin : A catechin with (2R,3R)-configuration.	3.8	10	0	catechin; polyphenol	antioxidant
gallocatechol (-)-epigallocatechin : A flavan-3,3',4',5,5',7-hexol having (2R,3R)-configuration.	2.59	2	0	catechin; flavan-3,3',4',5,5',7-hexol	antioxidant; food component; plant metabolite
hesperetin [no description available]	3.46	7	0	3'-hydroxyflavanones; 4'-methoxyflavanones; monomethoxyflavanone; trihydroxyflavanone	antineoplastic agent; antioxidant; plant metabolite
magnolol [no description available]	2.07	1	0	biphenyls
honokiol [no description available]	2.07	1	0	biphenyls
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.	4.14	4	0	benzodioxoles; furofuran; lignan	antineoplastic agent; neuroprotective agent; plant metabolite
chelerythrine chloride [no description available]	2.07	1	0
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.	2.44	2	0	diol; pentacyclic triterpenoid	analgesic; anti-inflammatory agent; antineoplastic agent; antiviral agent; metabolite
tetrahydroalstonine tetrahydroalstonine : A heteropentacyclic compound that is (20alpha)-16,17-didehydro-18-oxayohimban which is substituted at position 16 by a methoxycarbonyl group and at position 19 by a methyl group. It is a metabolite found in several plant species.	2.07	1	0	methyl ester; organic heteropentacyclic compound; yohimban alkaloid	plant metabolite
hernandezine hernandezine: from Thalictrum glandulosissimum; structure given in first source; RN given refers to (1beta)-isomer; RN for cpd without isomeric designation not avail 3/91	2.07	1	0	bisbenzylisoquinoline alkaloid; isoquinolines
narciclasine narciclasine: antitumor alkaloid from bulbs of Narcissus species	2.25	1	0	phenanthridines	metabolite
picropodophyllin picropodophyllin: isolated from American May apple (Podophyllum); inhibits IGF-I autophosphorylation without interfering with tyrosine kinase activity. picropodophyllotoxin : An organic heterotetracyclic compound that has a furonaphthodioxole skeleton bearing 3,4,5-trimethoxyphenyl and hydroxy substituents.	2.07	1	0	furonaphthodioxole; lignan; organic heterotetracyclic compound	antineoplastic agent; insulin-like growth factor receptor 1 antagonist; plant metabolite; tyrosine kinase inhibitor
methyl fluorone black methyl fluorone black: structure	1.99	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.	7.11	1	0	naphthofuran; olefinic compound; sesquiterpene lactone	antineoplastic agent; apoptosis inducer; plant metabolite
indole-2-carboxylic acid [no description available]	2.05	1	0	indolyl carboxylic acid
tetrandrine tetrandrine: a bisbenzylisoquinoline that exhibits antifibrogenic activity	2.07	1	0	bisbenzylisoquinoline alkaloid; isoquinolines
(-)-catechin (-)-catechin : The (-)-enantiomer of catechin.	2.52	2	0	catechin	metabolite
dehydrocostus lactone dehydrocostus lactone : An organic heterotricyclic compound and guaianolide sesquiterpene lactone that is acrylic acid which is substituted at position 2 by a 4-hydroxy-3,8-bis(methylene)decahydoazulen-5-yl group and in which the hydroxy group and the carboxy group have undergone formal condensation to afford the corresponding gamma-lactone.	2.07	1	0	gamma-lactone; guaiane sesquiterpenoid; organic heterotricyclic compound; sesquiterpene lactone	antimycobacterial drug; antineoplastic agent; apoptosis inducer; cyclooxygenase 2 inhibitor; metabolite; trypanocidal drug
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.	3.35	1	0	eudesmane sesquiterpenoid; sesquiterpene lactone	antifungal agent; apoptosis inducer; plant metabolite
LSM-4272 [no description available]	2.31	1	0	beta-carbolines
hederagenin [no description available]	2.03	1	0	dihydroxy monocarboxylic acid; pentacyclic triterpenoid; sapogenin	plant metabolite
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.	2.11	1	0	aporphine alkaloid; quaternary ammonium ion	plant metabolite
madecassic acid [no description available]	2.07	1	0	monocarboxylic acid; pentacyclic triterpenoid; tetrol	antioxidant; plant metabolite
panaxadiol panaxadiol: a protopanaxadiol with the side chain cyclized into a pyran which is an artifact of acidic hydrolysis; RN refers to (3 beta,12 beta,20R)-isomer	2.07	1	0	triterpenoid saponin
tryptanthrine tryptanthrine: minor constituent of traditional Chinese medicine qing dai	2.07	1	0	alkaloid antibiotic; organic heterotetracyclic compound; organonitrogen heterocyclic compound
homoeriodictyol homoeriodictyol: structure in first source. homoeriodictyol : A trihydroxyflavanone that consists of 3'-methoxyflavanone in which the three hydroxy substituents are located at positions 4', 5, and 7.	2.07	1	0	3'-methoxyflavanones; 4'-hydroxyflavanones; monomethoxyflavanone; trihydroxyflavanone	flavouring agent; metabolite
stictic acid stictic acid: antioxidant from lichen, Usnea articulata; structure in first source	1.99	1	0	aromatic ether
perfluorooctane sulfonic acid perfluorooctane-1-sulfonic acid : A perfluoroalkanesulfonic acid that is octane-1-sulfonic acid in which all seventeen of the hydrogens that are attached to carbons hvae been replaced by fluorines.	3	1	0	perfluoroalkanesulfonic acid	antilipemic drug; persistent organic pollutant
4-hydroxyindole hydroxyindoles : Any member of the class of indoles carrying at least one hydroxy group.	2.07	1	0	hydroxyindoles; phenols
citronellal, (r)-isomer (R)-(+)-citronellal : The (3R)-stereoisomer of 3,7-dimethyloct-6-enal (citronellal).	2.01	1	0	citronellal
2',7'-dichlorodihydrofluorescein diacetate [no description available]	2.07	1	0
4'-methoxyflavone 4'-methoxyflavone: from seeds of Psoralea corylifolia (Fabaceae); structure in first source	2.05	1	0	ether; flavonoids
rosiglitazone [no description available]	2.54	2	0	aminopyridine; thiazolidinediones	EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor; ferroptosis inhibitor; insulin-sensitizing drug
5-hydroxymethyl-2-furoic acid 5-hydroxymethyl-2-furoic acid: structure in first source. 5-hydroxymethyl-2-furoic acid : A member of the class of furoic acids that is 2-furoic acid substituted at position 5 by a hydroxymethyl group.	2.5	2	0	aromatic primary alcohol; furoic acid	bacterial xenobiotic metabolite; fungal metabolite; human urinary metabolite; nematicide
3,4-dihydroxyphenylethanol 3,4-dihydroxyphenylethanol: serotonin metabolite; structure	2.47	2	0	catechols; primary alcohol	antineoplastic agent; antioxidant; metabolite
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.	2.07	1	0	3'-hydroxyflavanones; 4'-hydroxyflavanones; disaccharide derivative; flavanone glycoside; rutinoside; trihydroxyflavanone	antioxidant
asperuloside asperuloside : A iridoid monoterpenoid glycoside isolated from Galium verum.	2.49	2	0	acetate ester; beta-D-glucoside; gamma-lactone; iridoid monoterpenoid; monosaccharide derivative	metabolite
alpha-bergamotene alpha-bergamotene: RR (13434-59-4) refers to the (trans)-isomer. alpha-bergamotene : A sesquiterpene consisting of a bicyclo[3.1.1]hept-2-ene skeleton substituted at positions 2 and 6 by methyl groups and at position 6 by a 4-methylpent-3-en-1-yl group.	2.02	1	0	bridged compound; polycyclic olefin; sesquiterpene	plant metabolite; volatile oil component
coenzyme a [no description available]	7.94	4	0	adenosine 3',5'-bisphosphate	coenzyme; Escherichia coli metabolite; mouse metabolite
loganin [no description available]	3.34	6	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
7,8-dihydromethysticin [no description available]	2.07	1	0	2-pyranones; aromatic ether
gentiopicroside gentiopicroside: a secoiridoid in Gentiana with rearrangement to two pyran rings	2.15	1	0	glycoside
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
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.	8.62	9	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
loganic acid loganic acid: structure. loganic acid : A cyclopentapyran that is 1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid substituted at positions 1, 6 and 7 by beta-D-glucosyloxy, hydroxy and methyl groups respectively	2.15	1	0	alpha,beta-unsaturated monocarboxylic acid; cyclopentapyran; glucoside	plant metabolite
cinchonine [no description available]	2.07	1	0	(8xi)-cinchonan-9-ol; cinchona alkaloid	metabolite
fibrinogen Fibrinogen: Plasma glycoprotein clotted by thrombin, composed of a dimer of three non-identical pairs of polypeptide chains (alpha, beta, gamma) held together by disulfide bonds. Fibrinogen clotting is a sol-gel change involving complex molecular arrangements: whereas fibrinogen is cleaved by thrombin to form polypeptides A and B, the proteolytic action of other enzymes yields different fibrinogen degradation products.. D-iditol : The D-enantiomer of iditol.	5.05	2	1	iditol	fungal metabolite
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]	2.81	3	0	organic molecular entity	metabolite
lupinine lupinine: RN given refers to parent cpd(1R-trans)-isomer; structure	2.07	1	0	quinolizidine alkaloid
matrine [no description available]	2.07	1	0	alkaloid
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.	2.07	1	0	cyclic terpene ketone; pentacyclic triterpenoid	anti-inflammatory drug; antipyretic; non-narcotic analgesic; plant metabolite
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.	10.46	4	1	amino acid zwitterion; homocysteine; serine family amino acid	fundamental metabolite; mouse metabolite
quinine hydrochloride [no description available]	2.07	1	0
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
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
sarsasapogenin [no description available]	2.07	1	0	sapogenin
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.	2.21	1	0	pentacyclic triterpenoid; secondary alcohol	metabolite
7-amino-4-methylcoumarin 7-amino-4-methylcoumarin: RN given refers to parent cpd	3.1	1	0	7-aminocoumarins	fluorochrome
tetcyclacis [no description available]	1.97	1	0
nsc-87877 NSC-87877: potent Shp2 (nonreceptor protein tyrosine phosphatase) inhibitor; structure in first source	2.11	1	0
lopinavir [no description available]	3.4	2	0	amphetamines; dicarboxylic acid diamide	anticoronaviral agent; antiviral drug; HIV protease inhibitor
gamma-tocopherol gamma-Tocopherol: A natural tocopherol with less antioxidant activity than ALPHA-TOCOPHEROL. It exhibits antioxidant activity by virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus. As in BETA-TOCOPHEROL, it also has three methyl groups on the 6-chromanol nucleus but at different sites.. gamma-tocopherol : A tocopherol in which the chroman-6-ol core is substituted by methyl groups at positions 7 and 8. It is found particularly in maize (corn) oil and soya bean (soybean) oils.	2.13	1	0	tocopherol; vitamin E	algal metabolite; food antioxidant; plant metabolite
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
corynanthine Corynanthine: A stereoisomer of yohimbine.	2.07	1	0	yohimban alkaloid
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
prunin protein, prunus prunin protein, Prunus: a legumin-like type of globulin; structure given in first source. naringenin 7-O-beta-D-glucoside : A flavanone 7-O-beta-D-glucoside that is (S)-naringenin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	2.54	2	0	(2S)-flavan-4-one; 4'-hydroxyflavanones; dihydroxyflavanone; flavanone 7-O-beta-D-glucoside; monosaccharide derivative	antibacterial agent; antilipemic drug; hypoglycemic agent; metabolite
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
podocarpic acid podocarpic acid: structure. podocarpic acid : An abietane diterpenoid lacking the isopropyl substituent with an aromatic C-ring and a hydroxy group at the 12-position.	2.07	1	0	abietane diterpenoid
harmol hydrochloride [no description available]	3.53	2	0
5-Methoxyflavone 5-methoxyflavone: DNA polymerase-beta inhibitor and neuroprotective agent against beta-amyloid toxicity; structure in first source	2.07	1	0	ether; flavonoids
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.	2.17	1	0	D-glucuronic acid	algal metabolite
diffractaic acid difractaic acid: from Lichen, Usnea steineri; active against Gram-positive, multidrug-resistant bacteria; structure in first source	1.99	1	0	carbonyl compound
4',5,6,7-tetramethoxyflavone 4',5,6,7-tetramethoxyflavone: structure given in first source; from plant Eupatorium odoratum. 4',5,6,7-tetramethoxyflavone : A tetramethoxyflavone that is the tetra-O-methyl derivative of scutellarein.	2.03	1	0	tetramethoxyflavone	antimutagen; plant metabolite
2-(4-hydroxyphenyl)-5,6,7,8-tetrahydroxy-4H-1-benzopyran-4-one 2-(4-hydroxyphenyl)-5,6,7,8-tetrahydroxy-4H-1-benzopyran-4-one : A pentahydroxyflavone that is flavone substituted by hydroxy groups at positions 5, 6, 7, 8, and 4' respectively.	2.03	1	0	pentahydroxyflavone
eupatorin eupatorin: a flavonoid from the East Asian medicinal plant Orthosiphon spicatus; prevents oxidative inactivation of 15-lipoxygenase; structure given in first source. eupatorin : A trimethoxyflavone that is 6-hydroxyluteolin in which the phenolic hydogens at positions 4', 6 and 7 have been replaced by methyl groups.	3.35	1	0	dihydroxyflavone; polyphenol; trimethoxyflavone	anti-inflammatory agent; antineoplastic agent; apoptosis inducer; Brassica napus metabolite; calcium channel blocker; P450 inhibitor; vasodilator agent
10-hydroxycamptothecin [no description available]	2.07	1	0	pyranoindolizinoquinoline
3,5,7,3',4'-pentamethoxyflavone 3,5,7,3',4'-pentamethoxyflavone: causes relaxation of cavernosum; structure in first source	2.25	1	0
1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid 1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid: structure given in first source; RN given refers to cpd without isomeric designation. 1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid : A member of the class of beta-carbolines that is 1,2,3,4-tetrahydro-beta-carboline substituted at position 3 by a carboxy group.	2.04	1	0	alpha-amino acid; aromatic amino acid; beta-carboline alkaloid	human urinary metabolite; human xenobiotic metabolite; plant metabolite; rat metabolite
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
zpck ZPCK: alkylates histidine residue at active center of bovine chymotrypsin	2.31	1	0
syringaresinol [no description available]	2.08	1	0	aromatic ether; furofuran; lignan; polyether; polyphenol	plant metabolite
arctiin arctiin: from fruits of Arctium lappa L; RN given refers to (3R-trans)-isomer; RN for cpd without isomeric designation not avail 12/92	3.95	12	0	glycoside; lignan
3,4,5-trihydroxybenzohydroxamic acid [no description available]	1.99	1	0
corydaline [no description available]	7.49	2	0	isoquinoline alkaloid; isoquinolines
demissidine [no description available]	2.07	1	0	alkaloid; organic heteropolycyclic compound; steroid
tingenone tingenone: quinonoid triterpene isolated from Euonymus tingens	2.31	1	0
cycloleucalenol cycloleucalenol: structure	2.13	1	0	3beta-sterol; pentacyclic triterpenoid; phytosterols
cinchonidine cinchonidine: has antimalarial activity; diastereoisomer of cinchonine with distinct physiochemical properties; RN given refers to parent cpd(8alpha,9R)-isomer. cinchonidine : 8-epi-Cinchonan in which a hydrogen at position 9 is substituted by hydroxy (R configuration). A diasteroisomer of cinchonine, it occurs in the bark of most varieties of Cinchona shrubs, and is frequently used for directing chirality in asymmetric synthesis.	2.07	1	0	(8xi)-cinchonan-9-ol; cinchona alkaloid	metabolite
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
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.	2.72	3	0	aromatic ether; secondary amino compound	metabolite
hydrogen sulfite [no description available]	2.06	1	0	sulfur oxoanion	human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
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.	2.21	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
fluo-3 Fluo-3: fluorescent Ca(2+) indicator; permits continuous monitoring of Ca without interference with use of UV-sensitive caged compounds	2.08	1	0	xanthene dye	fluorochrome
propidium iodide [no description available]	2.07	1	0	organic iodide salt
3-((3-cholamidopropyl)dimethylammonium)-1-propanesulfonate 3-((3-cholamidopropyl)dimethylammonium)-1-propanesulfonate: a surfactant; structure given in first source	2.4	2	0	1,1-diunsubstituted alkanesulfonate
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	2.07	1	0	beta-carbolines
geniposide [no description available]	10.47	18	0	terpene glycoside
phorbol-12-myristate [no description available]	2.25	1	0
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.	13.14	43	6	proanthocyanidin
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.	3	4	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
deguelin deguelin: a natural product from Mundulea sericea; RN refers to (7aS-cis)-isomer; structure given in first source. deguelin : A rotenone that is 13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one substituted by methoxy groups at positions 9 and 10, and by two methyl groups at position 3 (the 7aS,13aS-stereoisomer). It exists in abundant quantities in the bark, roots, and leaves of the Leguminosae family of plants and reported to exert anti-tumour effects in various cancers.	2.07	1	0	aromatic ether; diether; organic heteropentacyclic compound; rotenones	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; antiviral agent; apoptosis inducer; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; mitochondrial NADH:ubiquinone reductase inhibitor; plant metabolite
catechin (+)-catechin monohydrate : The monohydrate of (+)-catechin.	2.07	1	0	hydrate	geroprotector
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).	2.07	1	0	7-hydroxyisoflavones 7-O-beta-D-glucoside; hydroxyisoflavone; monosaccharide derivative	plant metabolite
parinaric acid parinaric acid: long-chain polyenoic fatty acid; RN given refers to cpd without isomeric designation. parinaric acid : An octadecatetraenoic acid containing a conjugated system of double bonds at positions 9, 11, 13 and 15.	2.67	3	0	octadecatetraenoic acid
triptolide [no description available]	4.06	3	0	diterpenoid; epoxide; gamma-lactam; organic heteroheptacyclic compound	antispermatogenic agent; plant metabolite
cafestol [no description available]	8.37	14	0	diterpenoid; furans; organic heteropentacyclic compound; primary alcohol; tertiary alcohol	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; antioxidant; apoptosis inducer; hypoglycemic agent; plant metabolite
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.	4.38	4	1
parthenolide [no description available]	2.07	1	0	germacranolide
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.	2.08	1	0	2-acetyl-1-alkyl-sn-glycero-3-phosphocholine	antihypertensive agent; beta-adrenergic antagonist; bronchoconstrictor agent; hematologic agent; vasodilator agent
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.	2.73	3	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
homoorientin homoorientin: isolated from Swertia japonica; structure given in first source	5.6	4	1	flavone C-glycoside; tetrahydroxyflavone	antineoplastic agent; radical scavenger
kahweol [no description available]	8.14	11	0	diterpenoid; furans; organic heteropentacyclic compound; primary alcohol; tertiary alcohol	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; antioxidant; apoptosis inducer; plant metabolite
valerates Valerates: Derivatives of valeric acid, including its salts and esters.	2.1	1	0	short-chain fatty acid anion; straight-chain saturated fatty acid anion	plant metabolite
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.	2.54	2	0	4',7-dihydroxyflavanone	hormone agonist; plant metabolite
ibuprofen, (r)-isomer [no description available]	3.1	1	0	ibuprofen
tanshinone tanshinone: from root of Salvia miltiorrhiza Bunge; RN given refers to tanshinone I; cardioprotective agent and neuroprotective agent	2.79	3	0	abietane diterpenoid	anticoronaviral agent
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
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
gastrodin gastrodin: the glucoside of 4-hydroxybenzyl alcohol (gastrodigenin); isolated from Gastrodia elata Blume;	2.21	1	0	glycoside
asiatic acid [no description available]	2.48	2	0	monocarboxylic acid; pentacyclic triterpenoid; triol	angiogenesis modulating agent; metabolite
cynaropicrin cynaropicrin: structure given in first source; RN given for ((3aR-(3aalpha,4alpha,6aalpha,8beta,9aalpha,9bbeta)))-isomer	2.13	1	0	sesquiterpene lactone
matairesinol matairesinol: lignan that is a central precursor in plants in the biosynthesis of numerous lignans (coordinate with specific); RN refers to (3R-trans)-isomer. (-)-matairesinol : A lignan that is gamma-butyrolactone in which the 3 and 4 positions are substituted by 4-hydroxy-3-methoxybenzyl groups (the 3R,4R-diastereomer).	2.1	1	0	gamma-lactone; lignan; polyphenol	angiogenesis inhibitor; anti-asthmatic agent; phytoestrogen; plant metabolite
benzo(a)pyrene-3,6-quinol [no description available]	3.1	1	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.	2.47	2	0	fatty acid anion 8:0; straight-chain saturated fatty acid anion	human metabolite; Saccharomyces cerevisiae metabolite
carboxypolymethylene carbomer: high molecular polyanionic substance	2.1	1	0
angustmycin a angustmycin A: structure; from Streptomyces hygroscopicus; inhibits GMP synthesis	2.07	1	0	6-aminopurines
razadyne Razadyne: Name of the FDA approved preparation from J&J.	2.07	1	0
alliin alliin: nutritional supplement in diet; possible therapeutic use in anemia and splenic hypertrophy; structure. alliin : An L-alanine derivative in which one of the methyl hydrogens of L-alanine has been replaced by an (S)-allylsulfinyl group.	2.13	1	0	alpha-amino acid
phytosphingosine phytosphingosine: differ with an additional hydroxyl at C-4 & no double bond between C-4 & C-5	2.07	1	0	amino alcohol; sphingoid; triol	mouse metabolite; Saccharomyces cerevisiae metabolite
dolichol-d-glucosylmonophosphate beta-D-glucose 1-phosphate : The beta-anomer of D-glucose 1-phosphate.	2	1	0	D-glucopyranose 1-phosphate
tetradecanoylphorbol acetate [no description available]	2.07	1	0
astragaloside a [no description available]	2.41	1	0
celastrol [no description available]	2.54	2	0	monocarboxylic acid; pentacyclic triterpenoid	anti-inflammatory drug; antineoplastic agent; antioxidant; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; Hsp90 inhibitor; 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.	5.64	16	1	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.	2.07	1	0	furonaphthodioxole; organic heterotetracyclic compound; phenols	antineoplastic 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.	2.06	1	0	4'-hydroxyflavanones; dihydroflavonols; secondary alpha-hydroxy ketone; tetrahydroxyflavanone	metabolite
phenoxy radical phenoxy radical : An organic radical generated from phenol.	1.99	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).	4.66	8	0	nitrogen oxoacid
n-(n-(3-carboxyoxirane-2-carbonyl)leucyl)isoamylamine N-(N-(3-carboxyoxirane-2-carbonyl)leucyl)isoamylamine: inhibits calcium-activated neutral protease; see also record for E-64; RN given refers to (2-S-(2alpha,3beta)(R*)-isomer)	2.07	1	0	leucine derivative
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.	2.57	2	0	L-lysine derivative; non-proteinogenic L-alpha-amino acid	antigen
e 64 E 64: cysteine protease inhibitor of microbial origin, which inhibits cathepsin B (EC 3.4.22.1) and cathepsin L (EC 3.4.22.-)	2.07	1	0	dicarboxylic acid monoamide; epoxy monocarboxylic acid; guanidines; L-leucine derivative; zwitterion	antimalarial; antiparasitic agent; protease inhibitor
proanthocyanidin a2 procyanidin A2: structure in first source. proanthocyanidin A2 : A proanthocyanidin obtained by the condensation of (-)-epicatechin units.	2.52	2	0	hydroxyflavan; proanthocyanidin	angiogenesis modulating agent; anti-HIV agent; antioxidant; metabolite
tetrahydrocurcumin tetrahydrocurcumin : A beta-diketone that is curcumin in which both of the double bonds have been reduced to single bonds.	2.75	3	0	beta-diketone; diarylheptanoid; polyphenol	metabolite
eriodictyol 7-glucuronide eriodictyol 7-glucuronide: from Davallia mariesii; structure given in first source; RN given refers to (R)-isomer. (2R)-eriodictoyl-7-O-beta-D-glucopyranosiduronic acid : A beta-D-glucosiduronic acid that is the 7-O-glucuronide of (2R)-eriodictyol. Isolated from the flowers of Chrysanthemum indicum, it exhibits inhibitory activity for rat lens aldose reductase.	2.01	1	0	3'-hydroxyflavonoid; beta-D-glucosiduronic acid	EC 1.1.1.21 (aldehyde reductase) inhibitor; metabolite
tert-butyl beta-carboline-3-carboxylate tert-butyl beta-carboline-3-carboxylate: benzodiazepine receptor antagonist	2.05	1	0
1,3-bis(tris(hydroxymethyl)methylamino)propane bis-tris propane : A water-soluble buffer substance used for the preparation of the biochemical and biological buffer solutions; pKa = 6.8 at 20 degreeC.	2	1	0	hexol	buffer
methotrexate [no description available]	2.78	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
1,4-dideoxy-1,4-iminoarabinitol 1,4-dideoxy-1,4-iminoarabinitol: RN given refers to (2S-(2alpha,3beta,4alpha))-isomer; structure given in first source	2.02	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.	3.18	5	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.	8.38	6	0	5-hydroxyanthocyanidin	antioxidant; metabolite; neuroprotective agent
xylose xylopyranose: structure in first source	2.06	1	0	D-xylose
phytol [no description available]	3.51	1	0
sinensetin sinensetin: isolated from citrus fruit; exhibit antiadhesive action on platelets. sinensetin : A pentamethoxyflavone that is flavone substituted by methoxy groups at positions 5, 6, 7, 3' and 4' respectively.	2.07	1	0	pentamethoxyflavone	plant metabolite
3',4'-dihydroxyflavone 3',4'-dihydroxyflavone: inhibitors of arachidonic acid peroxidation	2.25	1	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.	3.39	7	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.	2.47	2	0
harmalol hydrochloride [no description available]	2.07	1	0
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.	7.25	1	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
5-hydroxy-3',4',6,7-tetramethoxyflavone 5-hydroxy-3',4',6,7-tetramethoxyflavone: isolated from Artemisia argyi	3.35	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.	2.31	1	0	aromatic ether; cyclopropanes; fluoroquinolone antibiotic; pyrrolidinopiperidine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone	antibacterial drug
hyoscyamine Hyoscyamine: The 3(S)-endo isomer of atropine.. (S)-atropine : An atropine with a 2S-configuration.	2.07	1	0	tropane alkaloid
schizandrin a schizandrin A: the major lignan, 2-9%, of Schisandra plant; has hepatoprotective, antioxidant, and antineoplastic activities	2.07	1	0
atractylenolide iii atractylenolide III: from Atractylodes macrocephala Koidz; structure in first source	2.08	1	0	naphthofuran	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.	3.53	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
hydroxyl radical Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.	5.03	9	1	oxygen hydride; oxygen radical; reactive oxygen species
schizandrin b (+)-schisandrin B : An organic heterotetracyclic compound that is found in Fructus Schisandrae and Schisandra chinensis.	2.07	1	0	aromatic ether; cyclic acetal; organic heterotetracyclic compound; oxacycle; tannin	anti-asthmatic agent; anti-inflammatory agent; antilipemic drug; antioxidant; apoptosis inhibitor; hepatoprotective agent; nephroprotective agent; neuroprotective agent; plant metabolite
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.	2.43	2	0	camphor
rhodioloside [no description available]	2.13	1	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'.	8.02	4	0	5-hydroxyanthocyanidin	biological pigment; metabolite
gadolinium oxide gadolinium oxide: RN given refers to cpd with MF of Gd2-O3	2.17	1	0
celastrol methyl ester celastrol methyl ester: isolated from Tripterygium wilfordii; potent inhibitory activity on both Kir2.1 and ERG1 potassium channels, leading to LONG QT SYNDROME	2.31	1	0	carboxylic ester
hirudonine hirudonine: RN given refers to parent cpd; structure	2	1	0
miltirone miltirone: from Salvis miltiorrhiza Bunge; central benzodiazepine receptor ligand; structure given in first source	2.31	1	0	abietane diterpenoid
cirsiliol cirsiliol: potent inhibitor of arachidonate lipooxygenase. cirsiliol : A dimethoxyflavone that is flavone substituted by methoxy groups at positions 6 and 7 and hydroxy groups at positions 5, 3' and 4' respectively.	3.35	1	0	dimethoxyflavone; trihydroxyflavone	plant metabolite
cryptotanshinone cryptotanshinone: from Salvia miltiorrhiza	2.54	2	0	abietane diterpenoid	anticoronaviral agent
isosakuranetin isosakuranetin: structure in first source. 4'-methoxy-5,7-dihydroxyflavanone : A dihydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5 and 7 and a methoxy group at position 4' (the 2S stereoisomer).	2.07	1	0	(2S)-flavan-4-one; 4'-methoxyflavanones; dihydroxyflavanone; monomethoxyflavanone	plant metabolite
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.	2.07	1	0	guaiacols; lignan; polyphenol; primary alcohol	plant metabolite
vanillactic acid vanillactic acid: metabolite of catecholamines	2.06	1	0	2-oxo monocarboxylic acid
sweroside [no description available]	3	4	0	glycoside
secologanin (-)-secologanin : An iridoid monoterpenoid that is acetaldehyde in which on of the hydrogens of the methyl group has been replaced by a 2-(beta-D-glucopyranosyloxy)-3,4-dihydro-2H-pyran-4-yl group which is substituted at positions 3 and 5 by a vinyl and a methoxycarbonyl group, respectively (the 2S,3R,4S stereoisomer).	2.13	1	0	aldehyde; beta-D-glucoside; enoate ester; methyl ester; pyrans; secoiridoid glycoside	plant metabolite
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.	2.25	1	0	dihydromyricetin; secondary alpha-hydroxy ketone	antineoplastic agent; antioxidant; metabolite
dihydroguaiaretic acid dihydroguaiaretic acid: lignan extracted form Larrea divaricata; inhibitory to beef heart mitochondrial succinoxidase & NADH-oxidase; RN given refers to cpd without isomeric designation	2.1	1	0
capsidiol capsidiol: isolated from cultured cells of Nicotiana silvestris; structure given in first source. capsidiol : An eremophilane sesquiterpenoid that is (+)-5-epi-aristolochene bearing additional 1beta- and 3alpha-hydroxy substituents. It is a phytoalexin produced in Nicotiana and Capsicum plant species in response to pathogen attack.	2.07	1	0	eremophilane sesquiterpenoid; octahydronaphthalenes; sesquiterpene phytoalexin	antifungal agent; plant metabolite
isovitexin [no description available]	2.49	2	0	C-glycosyl compound; trihydroxyflavone	EC 3.2.1.20 (alpha-glucosidase) inhibitor; metabolite
cirsilineol cirsilineol: isolated from Thymus carnosus Boiss.. cirsilineol : A trimethoxyflavone that is flavone substituted by methoxy groups at positions 6, 7 and 3' and hydroxy groups at positions 5 and 4' respectively.	3.35	1	0	dihydroxyflavone; trimethoxyflavone	antineoplastic agent; plant metabolite
pannarin pannarin: photoirradiation of above cpd leads to its decomposition which is reduced by oxygen. pannarin : A member of the class of depsidones that is 11H-dibenzo[b,e][1,4]dioxepine substituted by methyl groups at positions 1,6 and 9, chloro group at position 2, hydroxy group at position 3, formyl group at position 4, methoxy group at position 8 and an oxo group at position 11. It is a lichen metabolite isolated from several Psoroma species.	1.99	1	0	aldehyde; aromatic ether; depsidones; organic heterotricyclic compound; organochlorine compound; phenols	antimicrobial agent; antineoplastic agent; apoptosis inducer; lichen 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	2.1	1	0
secoxyloganin secoxyloganin: from Guettarda playpoda. secoxyloganin : A secoiridoid glycoside that is [(2R,3R,4S)-2-hydroxy-5-(methoxycarbonyl)-3-vinyl-3,4-dihydro-2H-pyran-4-yl]acetic acid in which the anometric hydroxy group has been converted to the corresponding beta-D-glucoside. It has been isolated from several plant species and exhibits antioxidant and anti-allergic properties.	3.17	5	0	beta-D-glucoside; dicarboxylic acid monoester; enoate ester; methyl ester; monosaccharide derivative; pyrans; secoiridoid glycoside	anti-allergic agent; antioxidant; plant metabolite
sclareol sclareol: structure given in first source. sclareol : A labdane diterpenoid that is labd-14-ene substituted by hydroxy groups at positions 8 and 13. It has been isolated from Salvia sclarea.	2.07	1	0	labdane diterpenoid	antifungal agent; antimicrobial agent; apoptosis inducer; fragrance; plant metabolite
tanshinone ii a tashinone IIA: a cardiovascular agent with antineoplastic activity; isolated from Salvia miltiorrhiza; structure in first source	2.8	3	0	abietane diterpenoid
2-phenyl-1,2-benzisothiazol-3-(2h)-one 2-phenyl-1,2-benzisothiazol-3-(2H)-one: structure given in first source; sulfur analog of ebselen	2.31	1	0
4'-hydroxyflavanone 4'-hydroxyflavanone: structure in first source. 4'-hydroxyflavanones : Any hydroxyflavanone having a hydroxy substituent located at position 4'.	2.11	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.	2.03	1	0	iodine oxoanion; monovalent inorganic anion
leucodin leucodin: structure in first source	3.63	2	0	sesquiterpene lactone
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.	2.52	2	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
alpha-aminooxy-beta-phenylpropionic acid alpha-aminooxy-beta-phenylpropionic acid: inhibits phenylalanine ammonia-lyase; RN given refers to (S)-isomer	2.46	2	0
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).	5.4	3	1	amino acid zwitterion; angiotensin II	human metabolite
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	2.25	1	0
pinoresinol diglucoside pinoresinol diglucoside: major antihypertensive principle of Tu-Chung (Eucummia ulmoides, Oliver); structure	2.17	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.	2.01	1	0
yomogin yomogin: eudesmane sesquiterpene from Artemisia princeps; inhibits inducible nitric oxide synthase production in macrophages; structure in first source	3.35	1	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.	5.32	17	0
zm 241385 ZM 241385: a high affinity radioligand selective for the A2a adenosine receptor	2.1	1	0	diamino-1,3,5-triazine
2'-hydroxyflavanone [no description available]	2.11	1	0
organophosphonates hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.	5.29	3	1	divalent inorganic anion; phosphite ion
limonin [no description available]	2.07	1	0	epoxide; furans; hexacyclic triterpenoid; lactone; limonoid; organic heterohexacyclic compound	inhibitor; metabolite; volatile oil component
medioresinol medioresinol: has both leishmanicidal and antifungal activities; isolated from Sambucus williamsii; structure in first source. (-)-medioresinol : A lignan that is tetrahydro-1H,3H-furo[3,4-c]furan substituted by a 4-hydroxy-3,5-dimethoxyphenyl group at position 1 and a 4-hydroxy-3-methoxyphenyl group at position 4. It has been isolated from the stems of Sinocalamus affinis.	2.08	1	0	dimethoxybenzene; furofuran; lignan; polyphenol	plant metabolite
(+)-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.	5	8	1	glucosiduronic acid; glycosyloxyflavone; monosaccharide derivative; trihydroxyflavone	antineoplastic agent; proteasome inhibitor
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.	7.66	2	0	aflatoxin; aromatic ether; aromatic ketone	carcinogenic agent; human metabolite
benzyl d-glucopyranoside benzyl beta-D-glucopyranoside : A beta-D-glucoside that is beta-D-glucopyranose in which the hydroxy group at position 1R is substituted by a benzyloxy group.	3.42	2	0	benzenes; beta-D-glucoside	plant metabolite
carboxyebselen carboxyebselen: a nitric oxide synthase inhibitor	2.31	1	0
beta-alanine amide beta-alanine amide: structure. beta-alaninamide : An amino acid amide compound consisting of propionamide having a 3-amino substituent.	2.1	1	0	amino acid amide
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
maduramicin maduramicin: isolated from Actinomadura rubra	2.07	1	0
chelidonine chelidonine: benzophenanthridine derived from scoulerine from Chelidonium majus; RN given refers to parent cpd (chelidonine, (5bR-(5balpha,6beta,12alpha))-isomer)	2.07	1	0	alkaloid antibiotic; alkaloid fundamental parent; benzophenanthridine alkaloid
hydrastine [no description available]	2.02	1	0	isoquinolines	metabolite
(-)-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.	2.05	1	0	catechin; gallate ester; polyphenol	antineoplastic agent; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; human xenobiotic metabolite; plant metabolite
troleandomycin Troleandomycin: A macrolide antibiotic that is similar to ERYTHROMYCIN.. troleandomycin : A semi-synthetic macrolide antibiotic obtained by acetylation of the three free hydroxy groups of oleandomycin. Troleandomycin is only found in individuals that have taken the drug.	2.07	1	0	acetate ester; epoxide; macrolide antibiotic; monosaccharide derivative; polyketide; semisynthetic derivative	EC 1.14.13.97 (taurochenodeoxycholate 6alpha-hydroxylase) inhibitor; xenobiotic
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.	2.6	1	0	anabasine
cynarine 1,3-dicaffeoylquinic acid: structure in first source. 1,3-dicaffeoylquinic acid : An alkyl caffeate ester obtained by the formal condensation of hydroxy groups at positions 1 and 3 of ()-quinic acid with two molecules of trans-caffeic acid.	4.18	3	1
lapatinib [no description available]	7.11	1	0	furans; organochlorine compound; organofluorine compound; quinazolines	antineoplastic agent; tyrosine kinase inhibitor
darunavir Darunavir: An HIV PROTEASE INHIBITOR that is used in the treatment of AIDS and HIV INFECTIONS. Due to the emergence of ANTIVIRAL DRUG RESISTANCE when used alone, it is administered in combination with other ANTI-HIV AGENTS.. darunavir : An N,N-disubstituted benzenesulfonamide bearing an unsubstituted amino group at the 4-position, used for the treatment of HIV infection. A second-generation HIV protease inhibitor, darunavir was designed to form robust interactions with the protease enzyme from many strains of HIV, including those from treatment-experienced patients with multiple resistance mutations to other protease inhibitors.	2.31	1	0	carbamate ester; furofuran; sulfonamide	antiviral drug; HIV protease inhibitor
lenalidomide [no description available]	4.8	1	1	aromatic amine; dicarboximide; isoindoles; piperidones	angiogenesis inhibitor; antineoplastic agent; immunomodulator
1-methylpropyl-2-imidazolyl disulfide 1-methylpropyl-2-imidazolyl disulfide: a thioredoxin inhibitor with antineoplastic activity	2.31	1	0	imidazoles
santonin Santonin: Anthelmintic isolated from the dried unexpanded flower heads of Artemisia maritima and other species of Artemisia found principally in Russian and Chinese Turkestan and the Southern Ural region. (From Merck, 11th ed.)	2.07	1	0	botanical anti-fungal agent; santonin	plant metabolite
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.	2.07	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; C29-steroid; phytosterols; stigmastane sterol	anticholesteremic drug; antioxidant; mouse metabolite; plant metabolite; sterol methyltransferase inhibitor
deoxycholic acid Deoxycholic Acid: A bile acid formed by bacterial action from cholate. It is usually conjugated with glycine or taurine. Deoxycholic acid acts as a detergent to solubilize fats for intestinal absorption, is reabsorbed itself, and is used as a choleretic and detergent.. deoxycholic acid : A bile acid that is 5beta-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 12 respectively.	2.47	2	0	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human blood serum metabolite
3-nitrotyrosine 3-nitrotyrosine: RN given refers to parent cpd without isomeric designation. 3-nitrotyrosine : A nitrotyrosine comprising tyrosine having a nitro group at the 3-position on the phenyl ring.	3.28	6	0	2-nitrophenols; C-nitro compound; nitrotyrosine; non-proteinogenic alpha-amino acid
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.	8.48	7	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
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
vincristine sulfate [no description available]	2.07	1	0	organic sulfate salt	antineoplastic agent; geroprotector
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.	2.07	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.	3.21	5	0
lupeol [no description available]	4.11	3	0	pentacyclic triterpenoid; secondary alcohol	anti-inflammatory drug; plant metabolite
calendula Calendula: A plant genus of the family ASTERACEAE. Members contain CAROTENOIDS, essential oils (OILS, VOLATILE), flavonoids, mucilage, SAPONINS, and STEROLS. The plants are used both topically and internally. The common name of Marigold is also used for TAGETES.	2.08	1	0
acetylstrophanthidin acetylstrophanthidin: structure. acetylstrophanthidin : An acetate ester that is strophanidin acetylated at the 3beta-hydroxy group.	2.07	1	0	acetate ester	anti-arrhythmia drug
nsc 95397 [no description available]	2.31	1	0	1,4-naphthoquinones
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].	2.66	3	0
withaferin a withaferin A: an antiestrogen and phytogenic antineoplastic agent isolated from leaves of Withania somnifera Dun.; structure. withaferin A : A withanolide that is 5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione substituted by hydroxy groups at positions 4 and 27 (the 4beta,5beta,6beta,22R stereoisomer). Isolated from Physalis longifolia, it exhibits cytotoxic activity.	2.41	1	0	27-hydroxy steroid; 4-hydroxy steroid; delta-lactone; enone; epoxy steroid; ergostanoid; primary alcohol; secondary alcohol; withanolide	antineoplastic agent; apoptosis inducer
Harringtonine harringtonin: alkaloid C from Caphalotaxus fortunei	2.07	1	0	alkaloid
acivicin [no description available]	2.07	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
ketopinic acid ketopinic acid: structure in first source	2.07	1	0
wortmannin [no description available]	2.07	1	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
lariciresinol lariciresinol: found in human urine. (+)-lariciresinol : A lignan that is tetrahydrofuran substituted at positions 2, 3 and 4 by 4-hydroxy-3-methoxyphenyl, hydroxymethyl and 4-hydroxy-3-methoxybenzyl groups respectively (the 2S,3R,4R-diastereomer).	2.07	1	0	aromatic ether; lignan; oxolanes; phenols; primary alcohol	antifungal agent; 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.	5.22	11	1	(dihydroxyphenyl)propanoic acid	antioxidant; human xenobiotic metabolite
gitoxigenin gitoxigenin: structure	2.07	1	0	14beta-hydroxy steroid; 16beta-hydroxy steroid; 3beta-hydroxy steroid
graveoline graveoline: structure in first source	2.07	1	0	quinolines
4-oxy-6-(4-oxybezoyloxy)dauc-8,9-en 4-oxy-6-(4-oxybezoyloxy)dauc-8,9-en: RN given for (3R-(3alpha,3abeta,4beta,8aalpha))-isomer; a natural benzyl ester of a carotyl type azulene sesquiterpenoid; structure in first source	2.07	1	0
trimethoprim, sulfamethoxazole drug combination Trimethoprim, Sulfamethoxazole Drug Combination: A drug combination with broad-spectrum antibacterial activity against both gram-positive and gram-negative organisms. It is effective in the treatment of many infections, including PNEUMOCYSTIS PNEUMONIA in AIDS.. co-trimoxazole : A two-component mixture comprising trimethoprim and sulfamethoxazole.	2.08	1	0
nsc 663284 NSC 663284: structure in first source	2.31	1	0	quinolone
bortezomib [no description available]	10.25	2	1	amino acid amide; L-phenylalanine derivative; pyrazines	antineoplastic agent; antiprotozoal drug; protease inhibitor; proteasome inhibitor
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.	2.05	1	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.	2.03	1	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.	2.96	4	0
isomaltose [no description available]	2	1	0	glycosylglucose	human metabolite; metabolite; mouse metabolite
arabinose [no description available]	7.46	2	0	L-arabinose	Escherichia coli metabolite; mouse metabolite
n-acetylneuraminic acid N-Acetylneuraminic Acid: An N-acyl derivative of neuraminic acid. N-acetylneuraminic acid occurs in many polysaccharides, glycoproteins, and glycolipids in animals and bacteria. (From Dorland, 28th ed, p1518). N-acetylneuraminic acid : An N-acylneuraminic acid where the N-acyl group is specified as acetyl.	2.31	1	0	N-acetylneuraminic acids	antioxidant; bacterial metabolite; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor; human metabolite; mouse metabolite
fibrin Fibrin: A protein derived from FIBRINOGEN in the presence of THROMBIN, which forms part of the blood clot.	2.15	1	0	peptide
canavanine L-canavanine : A non-proteinogenic L-alpha-amino acid that is L-homoserine substituted at oxygen with a guanidino (carbamimidamido) group. Although structurally related to L-arginine, it is non-proteinogenic.	2.03	1	0	amino acid zwitterion; non-proteinogenic L-alpha-amino acid	phytogenic insecticide; plant metabolite
amylopectin Amylopectin: A highly branched glucan in starch.. amylopectin : A polydisperse highly branched polysaccharide derivative composed of chains of D-glucopyranose residues in alpha(1->4) glycosidic linkage. The chains are joined together by alpha(1->6) glycosidic linkages. A small number of alpha(1->3) glycosidic linkages and some 6-phosphate ester groups also may occur. The branches in amylopectin typically contain 24 to 30 glucose residues.	7.25	1	0
hexacyanoferrate iii hexacyanoferrate III: RN given refers to parent cpd	2.42	2	0
naringenin (S)-naringenin : The (S)-enantiomer of naringenin.	12.14	15	1	(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.	2.41	1	0
3-dehydroquinic acid 3-dehydroquinic acid: structure in first source. 3-dehydroquinic acid : A 4-oxo monocarboxylic acid derived from quinic acid by oxidation of the hydroxy group at position 3 to the corresponding keto group.	2.08	1	0	2-hydroxy monocarboxylic acid; 4-hydroxy monocarboxylic acid; 4-oxo monocarboxylic acid; 5-hydroxy monocarboxylic acid; secondary alpha-hydroxy ketone	Escherichia coli metabolite
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.	7.02	1	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	2.21	1	0	2-hydroxy monocarboxylic acid; catechols
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.	2.44	2	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
salicin [no description available]	7.06	1	0	aromatic primary alcohol; aryl beta-D-glucoside; benzyl alcohols	antipyretic; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; prodrug
scopolin [no description available]	7.97	4	0	beta-D-glucoside; coumarins; monosaccharide derivative	plant metabolite
puromycin [no description available]	2.07	1	0	puromycins	antiinfective agent; antimicrobial agent; antineoplastic agent; EC 3.4.11.14 (cytosol alanyl aminopeptidase) inhibitor; EC 3.4.14.2 (dipeptidyl-peptidase II) inhibitor; nucleoside antibiotic; protein synthesis inhibitor
taxifolin (+)-taxifolin : A taxifolin that has (2R,3R)-configuration.	4.58	7	0	taxifolin	metabolite
tartaric acid tartaric acid: RN given refers to cpd with unspecified isomeric designation. D-tartaric acid : The D-enantiomer of tartaric acid.	2.42	2	0	tartaric acid	Escherichia coli metabolite
l-bornesitol L-bornesitol: Antineoplastic Agents, Phytogenic from Hancornia speciosa; structure in first source. 1D-3-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 1S,2R,3R,4S,5S,6R-isomer).	2.11	1	0
cholesteryl glucoside cholesteryl glucoside: RN given refers to cpd without isomeric designation	2.05	1	0	monosaccharide derivative; sterol 3-beta-D-glucoside
mimosine L-mimosine : An L-alpha-amino acid that is propionic acid substituted by an amino group at position 2 and a 3-hydroxy-4-oxopyridin-1(4H)-yl group at position 3 (the 2S-stereoisomer). It a non-protein plant amino acid isolated from Mimosa pudica.	2.07	1	0	4-pyridones; amino acid zwitterion; non-proteinogenic L-alpha-amino acid	EC 1.14.18.1 (tyrosinase) inhibitor; plant metabolite
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.	4.11	4	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'.	7.75	3	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.	4.58	7	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.	2.69	3	0	cellotriose
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.	2.07	1	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
conessine conessine : A steroid alkaloid that is con-5-enine substituted by a N,N-dimethylamino group at position 3. It has been isolated from the plant species of the family Apocynaceae.	2.07	1	0	steroid alkaloid; tertiary amino compound	antibacterial agent; antimalarial; H3-receptor antagonist; plant metabolite
griseofulvin Griseofulvin: An antifungal agent used in the treatment of TINEA infections.. griseofulvin : An oxaspiro compound produced by Penicillium griseofulvum. It is used by mouth as an antifungal drug for infections involving the scalp, hair, nails and skin that do not respond to topical treatment.	2.48	2	0	1-benzofurans; antibiotic antifungal drug; benzofuran antifungal drug; organochlorine compound; oxaspiro compound	antibacterial agent; Penicillium metabolite
digitoxin Digitoxin: A cardiac glycoside sometimes used in place of DIGOXIN. It has a longer half-life than digoxin; toxic effects, which are similar to those of digoxin, are longer lasting. (From Martindale, The Extra Pharmacopoeia, 30th ed, p665). digitoxin : A cardenolide glycoside in which the 3beta-hydroxy group of digitoxigenin carries a 2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl trisaccharide chain.	2.07	1	0	cardenolide glycoside	EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor
hyperforin hyperforin: a prenylated acylphloroglucinol derivative; antibiotic component of novoimanine; psychoactive agent in St. John's wort; Russian; structure;. hyperforin : A cyclic terpene ketone that is a prenylated carbobicyclic acylphloroglucinol derivative produced by St. John's Wort, Hypericum perforatum.	3.31	6	0
abacavir abacavir: a carbocyclic nucleoside with potent selective anti-HIV activity. abacavir : A 2,6-diaminopurine that is (1S)-cyclopent-2-en-1-ylmethanol in which the pro-R hydrogen at the 4-position is substituted by a 2-amino-6-(cyclopropylamino)-9H-purin-9-yl group. A nucleoside analogue reverse transcriptase inhibitor (NRTI) with antiretroviral activity against HIV, it is used (particularly as the sulfate) with other antiretrovirals in combination therapy of HIV infection.	2.31	1	0	2,6-diaminopurines	antiviral drug; drug allergen; HIV-1 reverse transcriptase inhibitor
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
deltaline [no description available]	2.07	1	0	acetate ester; cyclic acetal; diterpene alkaloid; organic polycyclic compound; tertiary alcohol; tertiary amino compound
silychristin silychristin : A flavonolignan isolated from Silybum marianum and has been shown to exhibit inhibitory activities against lipoxygenase and prostaglandin synthetase.	2.25	1	0	1-benzofurans; aromatic ether; flavonolignan; polyphenol; secondary alpha-hydroxy ketone	lipoxygenase inhibitor; metabolite; prostaglandin antagonist; radical scavenger
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
petunidin petunidin: RN given for chloride salt. petunidin : An anthocyanidin cation that is flavylium bearing five hydroxy substituents at positions 3, 3', 4', 5 and 7 as well as a methoxy substituent at position 5'.	2.1	1	0	5-hydroxyanthocyanidin	plant metabolite
ruscogenin ruscogenin: basic sapogenin of Ruscus sp.; RN given refers to (1 beta,3 beta,25R)-isomer	2.11	1	0	triterpenoid
ginsenoside rf ginsenoside Rf: from ginseng. ginsenoside Rf : A ginsenoside found in Panax ginseng and Panax japonicus var. major that is dammarane which is substituted by hydroxy groups at the 3beta, 6alpha, 12beta and 20 pro-S positions, in which the hydroxy group at position 6 has been converted to the corresponding beta-D-glucopyranosyl-(1->2)-beta-D-glucopyranoside, and in which a double bond has been introduced at the 24-25 position.	2.05	1	0	12beta-hydroxy steroid; 20-hydroxy steroid; 3beta-hydroxy-4,4-dimethylsteroid; 3beta-hydroxy steroid; beta-D-glucoside; disaccharide derivative; ginsenoside; tetracyclic triterpenoid	antineoplastic agent; apoptosis inducer; plant metabolite
ferruginol ferruginol: structure in first source. ferruginol : An abietane diterpenoid that is abieta-8,11,13-triene substituted by a hydroxy group at positions 12.	2.31	1	0	abietane diterpenoid; carbotricyclic compound; meroterpenoid; phenols	antibacterial agent; antineoplastic agent; plant metabolite; protective agent
ingenol [no description available]	2.07	1	0	cyclic terpene ketone; tetracyclic diterpenoid
isopimaric acid isopimaric acid: isolated from the bark of Illicium jadifengpi	2.31	1	0	carbotricyclic compound; diterpenoid; monocarboxylic acid
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.	2.1	1	0	catechin; tetrahydroxyflavan	EC 3.2.1.20 (alpha-glucosidase) inhibitor; plant metabolite
picrotin picrotin: the less toxic component of PICROTOXIN lacking GABA activity. picrotin : An organic heteropentacyclic compound that is picrotoxinin in which the olefinic double bond has undergone addition of water to give the corresponding tertiary alcohol. It is the less toxic component of picrotoxin, lacking GABA activity.	2.07	1	0	diol; epoxide; gamma-lactone; organic heteropentacyclic compound; picrotoxane sesquiterpenoid; tertiary alcohol	plant metabolite
picrotoxinin [no description available]	2.07	1	0	epoxide; gamma-lactone; organic heteropentacyclic compound; picrotoxane sesquiterpenoid; tertiary alcohol	GABA antagonist; plant metabolite; serotonergic antagonist
naringin [no description available]	9.77	9	0	(2S)-flavan-4-one; 4'-hydroxyflavanones; dihydroxyflavanone; disaccharide derivative; neohesperidoside	anti-inflammatory agent; antineoplastic agent; metabolite
isonaringin isonaringin: structure in first source. narirutin : A disaccharide derivative that is (S)-naringenin substituted by a 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	2.07	1	0	(2S)-flavan-4-one; 4'-hydroxyflavanones; dihydroxyflavanone; disaccharide derivative; rutinoside	anti-inflammatory agent; antioxidant; 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.	2.76	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
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.	2.49	2	0	C-glycosyl compound; trihydroxyflavone	metabolite
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.	2.07	1	0	beta-hydroxy ketone; guaiacols	antineoplastic agent; plant metabolite
ononin [no description available]	2.07	1	0	4'-methoxyisoflavones; 7-hydroxyisoflavones 7-O-beta-D-glucoside; monosaccharide derivative	plant metabolite
securinine securinine: a quinolizine pseudoalkaloid (not from amino acid) from Securinega suffurutiosa or Securinini nitras	2.07	1	0	indolizines
hinokinin hinokinin: suppresses expression of both HBsAg and HBeAg. hinokinin : A lignan that is dihydrofuran-2(3H)-one (gamma-butyrolactone) substituted by a 3,4-methylenedioxybenzyl group at positions 3 and 4 (the 3R,4R-diastereoisomer).	2.11	1	0	benzodioxoles; gamma-lactone; lignan	trypanocidal drug
Dubinidine [no description available]	2.07	1	0	organic heterotricyclic compound; organonitrogen heterocyclic compound; oxacycle
alpha-chaconine alpha-chaconine: glycoside of solanidine; structure in 5th source	2.05	1	0	glycoalkaloid; steroid saponin
cyclopamine [no description available]	2.07	1	0	piperidines	glioma-associated oncogene inhibitor
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)	5.83	27	0
acanthoside b acanthoside B: isolated from the herb Huanghuaren; RN given refers to (1S-(1alpha,3aalpha,4alpha,6aalpha))-isomer	2.11	1	0	beta-D-glucoside	metabolite
acetylleucyl-leucyl-norleucinal acetylleucyl-leucyl-norleucinal: a proteasome inhibitor. acetylleucyl-leucyl-norleucinal : A tripeptide composed of N-acetylleucyl, leucyl and norleucinal residues joined in sequence.	2.31	1	0	aldehyde; tripeptide	cysteine protease inhibitor
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.	2	1	0	tripeptide
geniposidic acid [no description available]	8.69	9	0	terpene glycoside
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.	7.25	1	0	arsenic molecular entity; inorganic sodium salt	antibacterial agent; antifungal agent; antineoplastic agent; carcinogenic agent; herbicide; insecticide; rodenticide
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.	2.42	2	0	anthocyanin cation; aromatic ether; beta-D-glucoside	metabolite
doxorubicin hydrochloride [no description available]	2.07	1	0	anthracycline
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	2.07	1	0	alkaloid	geroprotector
dihydroergocristine monomesylate dihydroergocristine mesylate : The methanesulfonic acid salt of dihydroergocristine. It has been used as the for the symptomatic treatment of mental deterioration associated with cerebrovascular insufficiency and in peripheral vascular disease. It is also a component of ergoloid mesylate (codergocrine mesilate), a mixture of ergot alkaloid derivatives that is used as a vasodilator and has shown mild benefits in the treatment of vascular dementia.	2.07	1	0	methanesulfonate salt	alpha-adrenergic antagonist; geroprotector; vasodilator agent
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	3.32	6	0	cyclodextrin
acarbose [no description available]	2.04	1	0	amino cyclitol; glycoside
acetyl coenzyme a Acetyl Coenzyme A: Acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent.	2.41	1	0	acyl-CoA	acyl donor; coenzyme; effector; fundamental metabolite
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	7.36	29	0	cinnamic acid	plant metabolite
ergosterol [no description available]	8.55	2	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; ergostanoid; phytosterols	fungal metabolite; Saccharomyces cerevisiae metabolite
trichostatin a trichostatin A: chelates zinc ion in the active site of histone deacetylases, resulting in preventing histone unpacking so DNA is less available for transcription; do not confuse with TRICHOSANTHIN which is a protein; found in STREPTOMYCES	2.48	2	0	antibiotic antifungal agent; hydroxamic acid; trichostatin	bacterial metabolite; EC 3.5.1.98 (histone deacetylase) inhibitor; geroprotector
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.	4.2	5	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.	2.91	4	0	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
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.	2.13	1	0	butenedioic acid	food acidity regulator; fundamental metabolite; geroprotector
resveratrol trans-resveratrol : A resveratrol in which the double bond has E configuration.	6.62	19	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).	4.07	4	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.	3.52	6	0	octadec-9-enoic acid	antioxidant; Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; Escherichia coli metabolite; mouse metabolite; plant metabolite; solvent
ferulic acid ferulate : A monocarboxylic acid anion obtained by the deprotonation of the carboxy group of ferulic acid.	12.24	125	2	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.	3.2	4	0	D-galactopyranuronic acid
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.	2.52	2	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.	3.53	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
5-hydroxyferulic acid 5-hydroxyferulic acid : Ferulic acid in which the ring hydrogen at position 5 is substituted by a hydroxy group.. (E)-5-hydroxyferulic acid : The E-isomer of 5-hydroxyferulic acid.	2.15	1	0	5-hydroxyferulic acid
lycopene [no description available]	4.85	7	1	acyclic carotene	antioxidant; plant metabolite
gw 3965 GW 3965: a liver X receptor ligand	2.31	1	0	diarylmethane
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
alitretinoin Alitretinoin: A retinoid that is used for the treatment of chronic hand ECZEMA unresponsive to topical CORTICOSTEROIDS. It is also used to treat cutaneous lesions associated with AIDS-related KAPOSI SARCOMA.	2.07	1	0	retinoic acid	antineoplastic agent; keratolytic drug; metabolite; retinoid X receptor agonist
L-cycloserine L-cycloserine : A 4-amino-1,2-oxazolidin-3-one that has S configuration. An antibiotic isolated from Erwinia uredovora.	2.07	1	0	4-amino-1,2-oxazolidin-3-one	anti-HIV agent; anticonvulsant; EC 2.3.1.50 (serine C-palmitoyltransferase) inhibitor
gs 4071 GS 4071: The acid form.. oseltamivir acid : A cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid which is substituted at positions 3, 4, and 5 by pentan-3-yloxy, acetamido, and amino groups, respectively (the 3R,4R,5S enantiomer). An antiviral drug, it is used as the corresponding ethyl ester prodrug, oseltamivir, to slow the spread of influenza.	2.25	1	0	acetate ester; amino acid; cyclohexenecarboxylic acid; primary amino compound	antiviral drug; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor; marine xenobiotic metabolite
1,3,6-tri-o-galloyl-beta-d-glucose 1,3,6-tri-O-galloylglucose: structure in first source	2.15	1	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).	6.17	38	0
12-deoxyphorbol 13-acetate [no description available]	2.07	1	0	phorbol ester	metabolite
artenimol [no description available]	3.35	1	0
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)	2.07	1	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.	3.17	5	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; phytosterols	marine metabolite; plant metabolite
aphidicolin Aphidicolin: An antiviral antibiotic produced by Cephalosporium aphidicola and other fungi. It inhibits the growth of eukaryotic cells and certain animal viruses by selectively inhibiting the cellular replication of DNA polymerase II or the viral-induced DNA polymerases. The drug may be useful for controlling excessive cell proliferation in patients with cancer, psoriasis or other dermatitis with little or no adverse effect upon non-multiplying cells.. aphidicolin : A tetracyclic diterpenoid that has an tetradecahydro-8,11a-methanocyclohepta[a]naphthalene skeleton with two hydroxymethyl substituents at positions 4 and 9, two methyl substituents at positions 4 and 11b and two hydroxy substituents at positions 3 and 9. An antibiotic with antiviral and antimitotical properties. Aphidicolin is a reversible inhibitor of eukaryotic nuclear DNA replication.	2.07	1	0	tetracyclic diterpenoid	antimicrobial agent; antimitotic; antineoplastic agent; antiviral drug; apoptosis inducer; Aspergillus metabolite; DNA synthesis inhibitor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; fungal metabolite
benzyloxycarbonylleucyl-leucyl-leucine aldehyde benzyloxycarbonylleucyl-leucyl-leucine aldehyde: proteasome inhibitor. N-benzyloxycarbonyl-L-leucyl-L-leucyl-L-leucinal : A tripeptide that is L-leucyl-L-leucyl-L-leucine in which the C-terminal carboxy group has been reduced to the corresponding aldehyde and the N-terminal amino group is protected as its benzyloxycarbonyl derivative.	2.31	1	0	amino aldehyde; carbamate ester; tripeptide	proteasome inhibitor
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.	2.31	1	0	nucleoside analogue; phosphonic acids	antiviral drug; drug metabolite; HIV-1 reverse transcriptase inhibitor
(+)-usnic acid [no description available]	2.42	2	0	usnic acid
beta, beta-dimethylacrylshikonin, (+)-isomer [no description available]	2.07	1	0	hydroxy-1,4-naphthoquinone
shikonin shikonin: a naphthazarin; has antineoplastic and angiogenesis inhibiting activities	2.07	1	0	hydroxy-1,4-naphthoquinone
5,7,3',4',5'-pentamethoxyflavone 5,7,3',4',5'-pentamethoxyflavone: antineoplastic agent that reverses P-glycoprotein-mediated multidrug resistance; structure in first source	2.25	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).	2.41	2	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
maltitol maltitol : An alpha-D-glucoside consisting of D-glucitol having an alpha-D-glucosyl residue attached at the 4-position. Used as a sugar substitute.	2	1	0	alpha-D-glucoside; glycosyl alditol	laxative; metabolite; sweetening agent
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.	2.79	3	0	beta-D-glucoside; flavanone glycoside; monohydroxyflavanone; monosaccharide derivative	anti-inflammatory agent; anticoronaviral agent; plant metabolite
1-(2-Naphthylmethyl)-2,3-dioxo-indoline-5-carboxamide [no description available]	2.31	1	0	indolecarboxamide	anticoronaviral agent
potassium permanganate Potassium Permanganate: Permanganic acid (HMnO4), potassium salt. A highly oxidative, water-soluble compound with purple crystals, and a sweet taste. (From McGraw-Hill Dictionary of Scientific and Technical Information, 4th ed)	1.95	1	0
dipyrone Dipyrone: A drug that has analgesic, anti-inflammatory, and antipyretic properties. It is the sodium sulfonate of AMINOPYRINE.. metamizole sodium : An organic sodium salt of antipyrine substituted at C-4 by a methyl(sulfonatomethyl)amino group, commonly used as a powerful analgesic and antipyretic.	2.17	1	0	organic sodium salt	anti-inflammatory agent; antipyretic; antirheumatic drug; cyclooxygenase 3 inhibitor; non-narcotic analgesic; peripheral nervous system drug; prodrug
4-phenylcoumarin 4-phenylcoumarin: structure given in first source. 4-phenylcoumarin : The simplest member of the class of neoflavones that is coumarin substituted by a phenyl group at position 4.	2.5	2	0	neoflavones
iron tetraphenylporphyrin [no description available]	2.02	1	0
carbenoxolone sodium Carbenoxolone: An agent derived from licorice root. It is used for the treatment of digestive tract ulcers, especially in the stomach. Antidiuretic side effects are frequent, but otherwise the drug is low in toxicity.	2.08	1	0	triterpenoid
crotonic acid crotonic acid: a stereospecific unsaturated carboxylic acid found in CROTON OIL. butenoic acid : Any C4, straight-chain fatty acid containing one double bond.. crotonic acid : A but-2-enoic acid with a trans- double bond at C-2. It has been isolated from Daucus carota.	2.06	1	0	2-butenoic acid	plant metabolite
rhapontin rhapontin: constituent of rhubarb rhizome	2.07	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
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.	5.14	5	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
methyl cinnamate methyl cinnamate: RN given refers to cpd without isomeric designation. methyl cinnamate : A methyl ester resulting from the formal condensation of methyl cinnamic acid with methanol. It is found naturally in the essential oils of Alpinia and Basil leaf oil, and widely used in the flavor and perfume industries.. methyl trans-cinnamate : The E (trans) isomer of methyl cinnamate.	2.06	1	0	methyl cinnamate	antibacterial agent; fungal metabolite; nematicide; plant metabolite
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.	3.9	3	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.	4.46	6	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	55	0	4-coumaric acid	food component; mouse metabolite; plant metabolite
anethole anethole: an isomer of estragole; structurally similar to CAPSAICIN; has some neurological and insecticidal and skin absorption effects; RN given refers to unspecified stereoisomer. anethole : A monomethoxybenzene that is methoxybenzene substituted by a prop-1-en-1-yl group at position 4.. trans-anethole : The trans-stereoisomer of anethole.	1.99	1	0	anethole	flavouring agent
geraniol [no description available]	3.1	1	0	3,7-dimethylocta-2,6-dien-1-ol; monoterpenoid; primary alcohol	allergen; fragrance; plant metabolite; volatile oil component
glycosides [no description available]	7.25	71	0
3-Methoxycinnamic acid [no description available]	2.13	1	0	hydroxycinnamic acid
chalcone trans-chalcone : The trans-isomer of chalcone.	3.18	5	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.	4.66	8	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)	2.51	2	0	isomethyleugenol
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.	2.55	2	0	benzodioxoles; N-acylpiperidine; piperidine alkaloid; tertiary carboxamide	food component; human blood serum metabolite; NF-kappaB inhibitor; plant metabolite
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	4.17	15	0	stilbene
isoliquiritigenin [no description available]	2.07	1	0	chalcones	antineoplastic agent; biological pigment; EC 1.14.18.1 (tyrosinase) inhibitor; GABA modulator; geroprotector; metabolite; NMDA receptor antagonist
Methylenedioxycinnamic acid [no description available]	2.05	1	0	hydroxycinnamic acid
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.	2.46	2	0	alpha,beta-unsaturated monocarboxylic acid; sorbic acid
rauwolscine Rauwolscine: A stereoisomer of yohimbine.	2.07	1	0	methyl 17-hydroxy-20xi-yohimban-16-carboxylate
flavin-adenine dinucleotide Flavin-Adenine Dinucleotide: A condensation product of riboflavin and adenosine diphosphate. The coenzyme of various aerobic dehydrogenases, e.g., D-amino acid oxidase and L-amino acid oxidase. (Lehninger, Principles of Biochemistry, 1982, p972)	2.41	1	0	flavin adenine dinucleotide; vitamin B2	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; prosthetic group
amygdalin [no description available]	2.25	1	0
amygdalin (R)-amygdalin : An amygdalin in which the stereocentre on the cyanohydrin function has R-configuration.	2.07	1	0	amygdalin	antineoplastic agent; apoptosis inducer; plant metabolite
sodium metabisulfite sodium metabisulfite: request from searcher; RN given refers to disulfurous acid, di-Na salt. sodium disulfite : An inorganic sodium salt composed of sodium and disulfite ions in a 2:1 ratio.	2.1	1	0	inorganic sodium salt	food antioxidant
hydrastine, (r-(r,s))-isomer [no description available]	2.07	1	0	isoquinolines
nsc 4347 NSC 4347: structure in first source	2.55	2	0
sesquiterpenes [no description available]	6.12	22	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
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	1	0	aryl thiol; purines; thiocarbonyl compound	anticoronaviral agent; antimetabolite; antineoplastic agent
vasicine vasicine: RN given refers to (R)-isomer	2.07	1	0
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.	2.99	4	0	catechols; polyphenol; resorcinols; stilbenol	antineoplastic agent; apoptosis inducer; geroprotector; hypoglycemic agent; plant metabolite; protein kinase inhibitor; tyrosine kinase inhibitor
phenylthiourea Phenylthiourea: Phenylthiourea is a THIOUREA derivative containing a phenyl ring. Depending on their genetic makeup, humans can find it either bitter-tasting or tasteless.. N-phenylthiourea : A member of the class of thioureas that is thiourea in which one of the hydrogens is replaced by a phenyl group. Depending on their genetic makeup, humans find it either very bitter-tasting or tasteless. This unusual property resulted in N-phenylthiourea being used in paternity testing prior to the advent of DNA testing.	1.94	1	0	thioureas	EC 1.14.18.1 (tyrosinase) inhibitor
caffeic acid trans-caffeic acid : The trans-isomer of caffeic acid.	13.69	355	4	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.	3.71	9	0	alkyl caffeate ester; methyl ester
1-(4-Methoxyphenyl)-2-nitroethylene 4-methoxy-beta-nitrostyrene: has vasodilator activity; structure in first source	2.31	1	0	methoxybenzenes
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.	4.52	7	0	methoxycinnamic acid
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
ethyl ferulate ethyl ferulate: structure in first source	2.05	1	0
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.	2.07	1	0	N-alkylpyrrolidine; pyridines; pyrrolidin-2-ones; pyrrolidine alkaloid	antidepressant; biomarker; human xenobiotic metabolite; plant metabolite
heliotrine [no description available]	2.07	1	0	pyrrolizines
sclareolide [no description available]	2.07	1	0	naphthofuran
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.	8.37	30	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
hypocrellin b hypocrellin B: photosensitive pigments isolated from Hypocrella bambusae Sacc; structure given in first source	2.07	1	0
thiohydantoins Thiohydantoins: Sulfur analogs of hydantoins with one or both carbonyl groups replaced by thiocarbonyl groups.	4.8	1	1
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.	3.89	3	0	capsaicinoid	non-narcotic analgesic; TRPV1 agonist; voltage-gated sodium channel blocker
epalrestat epalrestat : A monocarboxylic acid that is 1,3-thiazolidine which is substituted on the nitrogen by a carboxymethyl group, at positions 2 and 4 by thioxo and oxo groups, respectively, and at position 5 by a 2-methyl-3-phenylprop-2-en-1-ylidene group. It is an inhibitor of aldose reductase (which catalyses the conversion of glucose to sorbitol) and is used for the treatment of some diabetic complications, including neuropathy.	2.07	1	0	monocarboxylic acid; thiazolidines	EC 1.1.1.21 (aldehyde reductase) inhibitor
beta-styrylacrylic acid beta-styrylacrylic acid: RN given refers to parent cpd; structure	2.06	1	0
aurapten aurapten: RN refers to (E)-isomer; structure given in first source. auraptene : A member of the class of coumarins that is umbelliferone in which the phenolic hydrogen has been replaced by a geranyl group. Ii is isolated from several edible fruits and vegetables and exhibits a variety of therapeutic properties.	2.07	1	0	coumarins; monoterpenoid	antihypertensive agent; antineoplastic agent; antioxidant; apoptosis inducer; dopaminergic agent; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; gamma-secretase modulator; gastrointestinal drug; hepatoprotective agent; matrix metalloproteinase inhibitor; neuroprotective agent; plant metabolite; PPARalpha agonist; vulnerary
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.	2.41	1	0	epoxide	metabolite
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.	4.8	1	1	one-carbon compound; thioureas; ureas	antioxidant; chromophore
D-fructopyranose [no description available]	6.45	14	1	cyclic hemiketal; D-fructose; fructopyranose	sweetening agent
potassium oxonate potassium oxonate: used to induce hyperuricemia in mice	2.31	1	0	organic molecular entity
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.	2.89	3	0	thiocarboxamide	hepatotoxic agent
tempo TEMPO: structure. TEMPO : A member of the class of aminoxyls that is piperidine that carries an oxidanediyl group at position 1 and methyl groups at positions 2, 2, 6, and 6, respectively.	2.04	1	0	aminoxyls; piperidines	catalyst; ferroptosis inhibitor; radical scavenger
fumonisin b2 fumonisin B2: produced by Fusarium moniliforme MRC 826; structure given in first source; has cancer-promoting ability. fumonisin B2 : A fumonisin that is (2S,3S,12S,14S,15R,16R)-2-amino-12,16-dimethylicosane-3,14,15-triol in which the hydroxy groups at positions 14 and 15 have each been esterified by condensation with the 1-carboxy group of 3-carboxyglutaric acid (giving a 3-carboxyglutarate ester group with R configuration in each case).	2.07	1	0	diester; diol; fumonisin; primary amino compound	Aspergillus metabolite; carcinogenic agent
tamoxifen [no description available]	7.76	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
1-butyl-3-methylimidazolium chloride 1-butyl-3-methylimidazolium chloride: structure in first source	2.15	1	0
1-butyl-3-methylimidazolium tetrafluoroborate [no description available]	2.21	1	0
nadp [no description available]	3.14	5	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)	5.32	50	0
5-(4-Chloro-benzenesulfonyl)-pyrimidine-2,4-diamine [no description available]	2.31	1	0	sulfonic acid derivative	anticoronaviral agent
S-[5-(trifluoromethyl)-4H-1,2,4-triazol-3-yl] 5-(phenylethynyl)furan-2-carbothioate [no description available]	2.31	1	0	acetylenic compound; furans; organofluorine compound; thioester; triazoles
artemotil artemotil: structure given in first source; RN given refers to cpd without isomeric designation	3.35	1	0	artemisinin derivative
lincomycin Lincomycin: An antibiotic produced by Streptomyces lincolnensis var. lincolnensis. It has been used in the treatment of staphylococcal, streptococcal, and Bacteroides fragilis infections.. lincomycin : A carbohydrate-containing antibiotic produced by the actinomyces Streptomyces lincolnensis.	2.07	1	0	carbohydrate-containing antibiotic; L-proline derivative; monocarboxylic acid amide; pyrrolidinecarboxamide; S-glycosyl compound	antimicrobial agent; bacterial metabolite
valinomycin Valinomycin: A cyclododecadepsipeptide ionophore antibiotic produced by Streptomyces fulvissimus and related to the enniatins. It is composed of 3 moles each of L-valine, D-alpha-hydroxyisovaleric acid, D-valine, and L-lactic acid linked alternately to form a 36-membered ring. (From Merck Index, 11th ed) Valinomycin is a potassium selective ionophore and is commonly used as a tool in biochemical studies.. valinomycin : A twelve-membered cyclodepsipeptide composed of three repeating D-alpha-hydroxyisovaleryl-D-valyl-L-lactoyl-L-valyl units joined in sequence. An antibiotic found in several Streptomyces strains.	2.07	1	0	cyclodepsipeptide; macrocycle	antimicrobial agent; antiviral agent; bacterial metabolite; potassium ionophore
estrone sulfate estrone sulfate: sulfoconjugated estrone; RN given refers to parent cpd	2.06	1	0	17-oxo steroid; steroid sulfate	human metabolite; mouse metabolite
thiamine disulfide thiamine disulfide: structure	1.95	1	0	aminopyrimidine; formamides; homoallylic alcohol; organic disulfide
telaprevir [no description available]	2.31	1	0	cyclopentapyrrole; cyclopropanes; oligopeptide; pyrazines	antiviral drug; hepatitis C protease inhibitor; peptidomimetic
8-hydroxypinoresinol 8-hydroxypinoresinol: cytoprotective lignan from Forsythia suspensa; structure in first source	2.06	1	0	lignan
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.	3.05	4	0
glycylproline Gly-Pro : A dipeptide consisting of L-proline having a glycyl residue attached to its alpha-amino group.	2.07	1	0	dipeptide zwitterion; dipeptide	metabolite
nitrogen dioxide Nitrogen Dioxide: Nitrogen oxide (NO2). A highly poisonous gas. Exposure produces inflammation of lungs that may only cause slight pain or pass unnoticed, but resulting edema several days later may cause death. (From Merck, 11th ed) It is a major atmospheric pollutant that is able to absorb UV light that does not reach the earth's surface.	7.44	2	0	nitrogen oxide
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]	3.8	1	1	cinchona alkaloid	antimalarial; muscle relaxant; non-narcotic analgesic
12-deoxyphorbolphenylacetate-20-acetate [no description available]	2.07	1	0
brassinin [no description available]	2.07	1	0	dithiocarbamic ester; indole phytoalexin
cystine [no description available]	1.94	1	0
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
chaetomellic acid a chaetomellic acid A: structure given in first source; an inhibitor of farnesyl-protein transferase	2.07	1	0
hirsutine [no description available]	2.07	1	0
3-deoxyvasicine, hydrochloride [no description available]	2.07	1	0
emetine dihydrochloride emetine dihydrochloride : The dihydrochloride salt of emetine.. emetine dihydrochloride hydrate : A hydrate that is the monohydrate of the dihydrochloride salt of emetine.	2.07	1	0	hydrochloride	anticoronaviral agent; antimalarial; antineoplastic agent; antiprotozoal drug; antiviral agent; autophagy inhibitor; emetic; protein synthesis inhibitor
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
piperolactam a piperolactam A: isolated from Houttynia cordata; structure in first source	2.13	1	0	alkaloid
ladanein ladanein: from Marrubium peregrinum; structure in first source. ladanein : A dimethoxyflavone that is scutellarein in which the hydroxy groups at positions 4' and 7 are replaced by methoxy groups. It is an effective anti-HCV agent.	2.03	1	0	dihydroxyflavone; dimethoxyflavone	antiviral agent; plant metabolite; radical scavenger
cytellin cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982	3.17	5	0
eugenyl-beta-d-glucopyranoside [no description available]	2.48	2	0
wogonoside wogonoside: from Scutellaria baicalensis; structure in first source. wogonin 7-O-beta-D-glucuronide : The glycosyloxyflavone which is the 7-O-glucuronide of wogonin.	2.07	1	0	beta-D-glucosiduronic acid; glycosyloxyflavone; monohydroxyflavone; monomethoxyflavone; monosaccharide derivative
salinomycin salinomycin: from Streptomyces albus; RN given refers to parent cpd; structure	2.07	1	0	polyketide; spiroketal	animal growth promotant; potassium ionophore
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.	2.52	2	0
silybin [no description available]	2.49	2	0
N-(4-Butan-2-ylphenyl)-N-[2-(cyclopentylamino)-2-oxo-1-pyridin-3-ylethyl]furan-2-carboxamide [no description available]	2.31	1	0	aromatic amide; furans	anticoronaviral agent
ovalbumin Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.	3.82	10	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.	2.46	2	0	organic sodium salt	detergent; protein denaturant
prohexadione-ca prohexadione-Ca: a 2-oxoglutarate-dependent dioxygenase inhibitor reduces the incidence and severity of fire blight caused by Erwinia amylovora and other plant diseases. prohexadione(2-) : An organic anion derived from prohexadione by deprotonation of both the carboxy group and a hydroxy group of any of the enolate forms of the triketo moiety. The corresponding calcium salt, prohexadione-calcium, is used as an anti-lodging agent in small-grain cereals.	2.01	1	0
crocin crocin: a free radical scavenger	3.33	6	0
galactomannan galactomannan: a galectin inhibitor. galactomannan : A heteroglycan consisting of a mannan backbone with galactose side groups.	2.07	1	0	oligosaccharide
8-(Trifluoromethyl)-9H-purin-6-amine [no description available]	2.31	1	0	6-aminopurines	anticoronaviral agent
l 663536 MK-886: orally active leukotriene biosynthesis inhibitor. 3-[3-(tert-butylsulfanyl)-1-(4-chlorobenzyl)-5-(propan-2-yl)-1H-indol-2-yl]-2,2-dimethylpropanoic acid : A member of the class of indoles that is 1H-indole substituted by a isopropyl group at position 5, a tert-butylsulfanediyl group at position 3, a 4-chlorobenzyl group at position 1 and a 2-carboxy-2-methylpropyl group at position 2. It acts as an inhibitor of arachidonate 5-lipoxygenase.	2.31	1	0	aryl sulfide; indoles; monocarboxylic acid; monochlorobenzenes	antineoplastic agent; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; leukotriene antagonist
Artemin [no description available]	3.35	1	0	sesquiterpene lactone
flavan-3-ol flavan-3-ol: structure in first source	6.44	4	1	hydroxyflavonoid
suramin sodium suramin(6-) : An organosulfate oxoanion that is the hexanion of suramin resulting from the deprotonation of the six sulfo groups; major species at pH 7.3.	2.31	1	0	organosulfate oxoanion
4-benzyl-2-methyl-1,2,4-thiadiazolidine-3,5-dione 4-benzyl-2-methyl-1,2,4-thiadiazolidine-3,5-dione: a GSK3beta inhibitor. TDZD-8 : A member of the class of thiadiazolidines that is 1,2,4-thiadiazolidine-3,5-dione which is substituted by a methyl group at position 2 and by a benzyl group at position 4. It is a non-ATP competitive inhibitor of glycogen synthase kinase 3beta (GSK3beta). An experimental compound which was being developed for the potential treatment of Alzheimer's disease.	2.31	1	0	benzenes; thiadiazolidine	anti-inflammatory agent; antineoplastic agent; apoptosis inducer; EC 2.7.11.26 (tau-protein kinase) inhibitor; neuroprotective agent
sodium borohydride sodium borohydride: RN given refers to parent cpd	1.99	1	0	inorganic sodium salt; metal tetrahydridoborate
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.	2.31	1	0	triazolopyrazine; trifluorobenzene	EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; environmental contaminant; hypoglycemic agent; serine proteinase inhibitor; xenobiotic
osteoprotegerin Osteoprotegerin: A secreted member of the TNF receptor superfamily that negatively regulates osteoclastogenesis. It is a soluble decoy receptor of RANK LIGAND that inhibits both CELL DIFFERENTIATION and function of OSTEOCLASTS by inhibiting the interaction between RANK LIGAND and RECEPTOR ACTIVATOR OF NUCLEAR FACTOR-KAPPA B.	2.15	1	0	long-chain fatty acid
sodium butyrate [no description available]	2.05	1	0	organic sodium salt	EC 3.5.1.98 (histone deacetylase) inhibitor; geroprotector
ginkgetin ginkgetin: from Cephalotaxus drupacea; biflavone; active against HSV-1; structure given in first source. ginkgetin : A biflavonoid that is the 7,4'-dimethyl ether derivative of amentoflavone. Isolated from Ginkgo biloba and Dioon, it exhibits anti-HSV-1, antineoplastic and inhibitory activities towards arachidonate 5-lipoxygenase and cyclooxygenase 2.	2.31	1	0	biflavonoid; hydroxyflavone; methoxyflavone; ring assembly	anti-HSV-1 agent; antineoplastic agent; cyclooxygenase 2 inhibitor; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; metabolite
ganhuangenin ganhuangenin: flavonoid from Scutellaria rehderiana; lipid peroxide antagonist	2.1	1	0
fraxetin fraxetin : A hydroxycoumarin that is 6-methoxycoumarin in which the hydrogens at positions 7 and 8 have been replaced by hydroxy groups.	2.13	1	0	aromatic ether; hydroxycoumarin	anti-inflammatory agent; antibacterial agent; antimicrobial agent; antioxidant; apoptosis inducer; apoptosis inhibitor; Arabidopsis thaliana metabolite; hepatoprotective agent; hypoglycemic agent
5,6-dehydrokawain 5,6-dehydrokawain: from Alpinia speciosa rhizoma; RN given for cpd without isomeric designation; structure given in first source	2.07	1	0	2-pyranones; aromatic ether
eupatilin eupatilin: isolated from Artemisia argyi. eupatilin : A trimethoxyflavone that is flavone substituted by hydroxy groups at C-5 and C-7 and methoxy groups at C-6, C-3' and C-4' respectively. Isolated from Citrus reticulata and Salvia tomentosa, it exhibits anti-inflammatory, anti-ulcer and antineoplastic activities.	3.93	3	0	dihydroxyflavone; trimethoxyflavone	anti-inflammatory agent; anti-ulcer drug; antineoplastic agent; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; metabolite
9,10-dihydrolysergol 9,10-dihydrolysergol: RN given refers to cpd without isomeric designation	2.07	1	0
quercetin 3-o-glucuronide quercetin 3-O-glucuronide: structure in first source. miquelianin : A quercetin O-glycoside that consists of quercetin attached to a beta-D-glucuronopyranosyl moiety at position 3 via a glycosidic linkage. Isolated from Salvia and Phaseolus vulgaris, it exhibits antioxidant and antidepressant activities.	2.81	3	0	beta-D-glucosiduronic acid; quercetin O-glycoside	antidepressant; antioxidant; metabolite
geranylgeranic acid geranylgeranic acid: RN given refers to cpd without isomeric designation. (2E,6E,10E)-geranylgeranic acid : A diterpenoid obtained by formal oxidation of the CH2OH group of (E,E,E)-geranylgeraniol to the corresponding carboxylic acid.	2.07	1	0	alpha,beta-unsaturated monocarboxylic acid; diterpenoid; methyl-branched fatty acid; trienoic fatty acid
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.	7.21	1	0	sphing-4-enine	human metabolite; mouse metabolite
quercetin [no description available]	12.96	190	4	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]	3.85	3	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.	4.35	18	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.	5.12	5	2	monocarboxylic acid; prostaglandins Falpha	human metabolite; mouse metabolite
biochanin a [no description available]	3.13	5	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]	2.76	3	0	4'-methoxyisoflavones; 7-hydroxyisoflavones	phytoestrogen; plant metabolite
prostaglandin b1 prostaglandin Bx: phospholipase A2 inhibitor; polymeric derivative of diketo-PGB1; mean MW 2,200. prostaglandin B1 : A member of the class of prostaglandins B that is prosta-8(12),13-dien-1-oic acid carrying oxo and hydroxy substituents at positions 9 and 15 respectively (the 13E,15S-stereoisomer).	2.07	1	0	prostaglandins B	human metabolite
sterigmatocystin [no description available]	2.07	1	0	sterigmatocystins	metabolite
12-oxophytodienoic acid 12-oxophytodienoic acid: structure given in first source; a jasmonate precursor that induces phytoalexin synthesis	2.21	1	0	carbocyclic fatty acid; olefinic fatty acid; oxo carboxylic acid
vitexin [no description available]	3.62	8	0	C-glycosyl compound; trihydroxyflavone	antineoplastic agent; EC 3.2.1.20 (alpha-glucosidase) inhibitor; plant metabolite; platelet aggregation inhibitor
acacetin 5,7-dihydroxy-4'-methoxyflavone : A monomethoxyflavone that is the 4'-methyl ether derivative of apigenin.	4.44	6	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.	8.28	47	1	trihydroxyflavone	antineoplastic agent; metabolite
luteolin [no description available]	9.8	67	4	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.	2.21	1	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.	3.14	5	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	1.99	1	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
quercitrin [no description available]	4.26	17	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]	6.31	19	0	hydroxycoumarin	plant growth regulator; plant metabolite
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.	5.93	23	1	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.	2.42	2	0	dihydroxy monocarboxylic acid; hydroxy polyunsaturated fatty acid; leukotriene; long-chain fatty acid	human metabolite; mouse metabolite; plant metabolite; vasoconstrictor agent
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.	2.49	2	0	epoxy monocarboxylic acid; thromboxanes A	mouse 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	2.49	2	0	tyramines	metabolite
4-coumaroylshikimic acid [no description available]	2.98	4	0	alpha,beta-unsaturated monocarboxylic acid; cyclohexenecarboxylic acid
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.	3.53	2	0	hydroxycoumarin	antineoplastic agent; hyaluronic acid synthesis inhibitor
daphnetin [no description available]	3.23	1	0	hydroxycoumarin
luteolin-7-glucuronide luteolin-7-glucuronide: isolated from Lycopus europaeus L.; active against pregnant mare serum gonadotropin. luteolin 7-O-beta-D-glucosiduronic acid : A luteolin glucosiduronic acid consisting of luteolin having a beta-D-glucosiduronic acid residue attached at the 7-position.	2.15	1	0	glycosyloxyflavone; luteolin O-glucuronoside; monosaccharide derivative; trihydroxyflavone	metabolite
5'-o-caffeoylquinic acid trans-5-O-caffeoyl-D-quinic acid : A cinnamate ester obtained by formal condensation of the carboxy group of trans-caffeic acid with the 5-hydroxy group of quinic acid.	4.12	4	0	cinnamate ester; cyclitol carboxylic acid	plant metabolite
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.	5.67	27	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.	2.1	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.	2.77	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.	2.01	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.	4.25	6	0	beta-D-glucoside; dihydroxyflavone; glycosyloxyflavone; monosaccharide derivative	antibacterial agent; metabolite; non-steroidal anti-inflammatory drug
alprostadil [no description available]	2.07	1	0	prostaglandins E	anticoagulant; human metabolite; platelet aggregation inhibitor; vasodilator agent
apiin apiin: structure. apiin : A beta-D-glucoside having a beta-D-apiosyl residue at the 2-position and a 5,4'-dihydroxyflavon-7-yl moiety at the anomeric position.	2.25	1	0	beta-D-glucoside; dihydroxyflavone; glycosyloxyflavone	EC 3.2.1.18 (exo-alpha-sialidase) inhibitor; plant 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.	3.51	1	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
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	3.68	9	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.	8.22	186	0	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite
kaempferol [no description available]	6.78	28	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.	2.08	1	0	prostaglandins Falpha	human metabolite; mouse metabolite
senecionine senecionine: RN given refers to parent cpd; structure. senecionine : A pyrrolizidine alkaloid isolated from the plant species of the genus Senecio.	2.07	1	0	lactone; pyrrolizidine alkaloid; tertiary alcohol	plant 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.	3.11	4	0	linolenic acid; omega-3 fatty acid	micronutrient; mouse metabolite; nutraceutical
naringenin chalcone naringenin chalcone: RN given refers to cpd with unspecified stereoisomer & from CA Vol 92 Form Index; RN for cpd not in Chemline 7/6/83; structure in first source. 2',4,4',6'-tetrahydroxychalcone : A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 2' ,4, 4', and 6' respectively.	2.43	2	0	chalcones; polyphenol	anti-allergic agent; anti-inflammatory agent; metabolite
genistein [no description available]	4.66	8	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.	2.77	3	0	antibiotic antifungal drug; macrolide antibiotic; polyene antibiotic	antiamoebic agent; antiprotozoal drug; bacterial metabolite
erucic acid [no description available]	2.05	1	0	docosenoic acid
nervonic acid (15Z)-tetracosenoic acid : A tetracosenoic acid having a cis-double bond at position 15.	2.05	1	0	tetracosenoic acid
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.	2.02	1	0	oxo monocarboxylic acid	jasmonates; plant metabolite
butein [no description available]	2.07	1	0	chalcones; polyphenol	antineoplastic agent; antioxidant; EC 1.1.1.21 (aldehyde reductase) inhibitor; geroprotector; hypoglycemic agent; plant metabolite; radiosensitizing agent; tyrosine kinase inhibitor
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.	8.04	4	0	carotenol	food colouring; plant metabolite
isobavachalcone isobavachalcone: RN given for (E)-isomer; structure in first source. isobavachalcone : A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 4, 2' and 4' and a prenyl group at position 3'.	2.31	1	0	chalcones; polyphenol	antibacterial agent; metabolite; platelet aggregation inhibitor
okanin okanin: hypoglycemic from Coreopsis tinctoria; structure in first source. okanin : A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 3, 4, 2', 3', and 4' respectively.	2.57	2	0	benzenetriol; chalcones	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	2.07	1	0	1-benzofurans
spinasterol spinasterol: RN given refers to alpha-spinasterol ((3beta,5alpha,22E)-isomer)	2.07	1	0	steroid
capillarisin capillarisin: from Artemisiae capillaris Herba.; structure	3.35	1	0	coumarins
5,7-dihydroxychromone 5,7-dihydroxychromone: isolated from the roots of Bauhinia hupehara	2.06	1	0	chromones
genistin genistin: glycoside of soy bean isoflavone, gentistein	2.47	2	0	7-hydroxyisoflavones 7-O-beta-D-glucoside
chartreusin chartreusin: structure	2.07	1	0	benzochromenone; glycoside
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.	3.78	3	0	hydroxycoumarin	antioxidant; plant metabolite; ultraviolet filter
esculin [no description available]	2.69	3	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.	4.33	3	0	hydroxycoumarin	fluorescent probe; food component; plant metabolite
alpha-farnesene alpha-farnesene: structure given in first source. alpha-farnesene : A farnesene that is 1,3,6,10-tetraene substituted by methyl groups at positions 3, 7 and 11 respectively.. farnesene : A sesquiterpene that is any of the four possible isomers of 3,7,11-trimethyl-1,3,6,10-dodecatetraene (alpha-farnesene) or of the two possible isomers of 7,11-dimethyl-3-methylene-1,6,10-dodecatriene.	2.58	2	0	alpha-farnesene
humulene humulene: structure given in first source. (1E,4E,8E)-alpha-humulene : The (1E,4E,8E)-isomer of alpha-humulene.	5.3	2	1	alpha-humulene
harpagoside harpagoside: glycoside of a cyclopenta[c]pyran from root of S. African plant Harpagophytum procumbens DC; structure in Negwer, 5th ed, #5281, 7th ed #9921; Harpagophytum extract WS 1531 is plant extract containing harpagoside; Antidiabetic Agent	7.1	1	0	terpene glycoside
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.	2.11	1	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
methysticin [no description available]	2.07	1	0	2-pyranones; aromatic ether
yangonin yangonin: structure in first source	2.07	1	0	2-pyranones; aromatic ether
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.	7.53	2	0	macrolide; resorcinols	fungal metabolite; mycoestrogen
amentoflavone [no description available]	8.01	4	0	biflavonoid; hydroxyflavone; ring assembly	angiogenesis inhibitor; antiviral agent; cathepsin B inhibitor; P450 inhibitor; plant metabolite
baicalein [no description available]	9.94	11	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.	4.51	7	0	7-hydroxyflavonol; dihydroxyflavone	anti-inflammatory agent; antineoplastic agent; antioxidant; EC 2.7.11.18 (myosin-light-chain kinase) inhibitor; hepatoprotective agent; plant metabolite
chrysosplenetin b chrysosplenetin B: constituent of the root of Berneuxia thibetica Decne. chrysosplenetin : A tetramethoxyflavone that is the 3,6,7,3'-tetramethyl ether derivative of quercetagetin.	2.1	1	0	dihydroxyflavone; tetramethoxyflavone	antiviral agent; plant metabolite
datiscetin datiscetin : A tetrahydroxyflavone that is 7-hydroxyflavonol bearing two additional hydroxy substituents at positions 2' and 5.	2.5	2	0	7-hydroxyflavonol; tetrahydroxyflavone
3,7,4'-trihydroxyflavone 3,7,4'-trihydroxyflavone: structure in first source	2.13	1	0	hydroxyflavan
diosmetin [no description available]	3.17	5	0	3'-hydroxyflavonoid; monomethoxyflavone; trihydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; antioxidant; apoptosis inducer; bone density conservation agent; cardioprotective agent; plant metabolite; tropomyosin-related kinase B receptor agonist; vasodilator agent
diosmin [no description available]	2.07	1	0	dihydroxyflavanone; disaccharide derivative; glycosyloxyflavone; monomethoxyflavone; rutinoside	anti-inflammatory agent; antioxidant
fisetin [no description available]	4.09	4	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.	3.53	2	0	7-hydroxyflavonol; trihydroxyflavone	antimicrobial agent; EC 3.1.1.3 (triacylglycerol lipase) inhibitor; plant metabolite
genkwanin genkwanin: structure. genkwanin : A monomethoxyflavone that is apigenin in which the hydroxy group at position 7 is methylated.	3.35	1	0	dihydroxyflavone; monomethoxyflavone	metabolite
hispidulin hispidulin : A monomethoxyflavone that is scutellarein methylated at position 6.	2.15	1	0	monomethoxyflavone; trihydroxyflavone	anti-inflammatory agent; anticonvulsant; antineoplastic agent; antioxidant; apoptosis inducer; 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.	4.6	24	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	7.97	4	0	C-glycosyl compound; xanthones	anti-inflammatory agent; antioxidant; hypoglycemic agent; plant metabolite
3-methylquercetin isorhamnetin : A monomethoxyflavone that is quercetin in which the hydroxy group at position 3' is replaced by a methoxy group.	5.4	10	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.	2.01	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.	3.15	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]	5.31	12	1	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.	2.49	2	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.	2.83	3	0	3'-hydroxyflavonoid; C-glycosyl compound; tetrahydroxyflavone	antioxidant; 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	1	0	flavonols; hexahydroxyflavone	antioxidant; antiviral agent; plant metabolite
rhamnetin rhamnetin: aglycone of xanthorhamnin; from Rhamnus. rhamnetin : A monomethoxyflavone that is quercetin methylated at position 7.	3.16	5	0	monomethoxyflavone; tetrahydroxyflavone	anti-inflammatory agent; antioxidant; 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'.	2.5	2	0	7-hydroxyflavonol; pentahydroxyflavone	plant metabolite
sciadopitysin sciadopitysin: biflavonoid from Taxus celebica & Ginkgo biloba. sciadopitysin : A biflavonoid that is a 7, 4', 4'''-trimethyl ether derivative of amentoflavone.	2.31	1	0	biflavonoid; hydroxyflavone; methoxyflavone; ring assembly	bone density conservation agent; platelet aggregation inhibitor
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.	2.31	1	0	tetrahydroxyflavone	metabolite
tamarixetin tamarixetin: isolated from Costsus spicatus. tamarixetin : A monomethoxyflavone that is quercetin methylated at position O-4'. Isolated from Cyperus teneriffae.	2.07	1	0	7-hydroxyflavonol; monomethoxyflavone; tetrahydroxyflavone	antioxidant; metabolite
tricetin tricetin : Flavone hydroxylated at positions 3', 4', 5, 5' and 7.	2.25	1	0	pentahydroxyflavone	antineoplastic agent; metabolite
tricin tricin: from Spartina cynosuroides and other plants; structure	3.03	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.	2.78	3	0	dihydroxyflavone; monomethoxyflavone	angiogenesis inhibitor; antineoplastic agent; cyclooxygenase 2 inhibitor; plant metabolite
coumestrol Coumestrol: A daidzein derivative occurring naturally in forage crops which has some estrogenic activity.. coumestrol : A member of the class of coumestans that is coumestan with hydroxy substituents at positions 3 and 9.	2.07	1	0	coumestans; delta-lactone; polyphenol	anti-inflammatory agent; antioxidant; plant metabolite
daidzein [no description available]	2.97	4	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
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
5-o-caffeoylshikimic acid 5-O-caffeoylshikimic acid: from bracken fern, Pteridium aquilinum; structure given in first source. 5-[(E)-caffeoyl]shikimic acid : A carboxylic ester obtained by formal condensation of the carboxy group of (E)-caffeic acid with the 5-hydroxy group of shikimic acid.	2.17	1	0	alpha,beta-unsaturated monocarboxylic acid; carboxylic ester; catechols; cyclohexenecarboxylic acid	plant metabolite
chicoric acid chicoric acid: inhibits HIV-1 integrase	9.85	32	0	organooxygen compound	geroprotector; HIV-1 integrase inhibitor
cynarine cynarine: active principle of the artichoke; functions primarily as a cholagogue and choleretic and also as antilipemic agent	10.62	27	0	alkyl caffeate ester; quinic acid	plant metabolite
echinacoside echinacoside: from Buddleja species; has antihepatotoxic activity	2.73	3	0	oligosaccharide
forsythiaside forsythiaside: RN given refers to (E)-isomer; structure given in first source; from the unripe fruit of Forsythia suspensa (qinglianquiao)	3.85	11	0	hydroxycinnamic acid
3,4-di-o-caffeoylquinic acid 3,4-di-O-caffeoylquinic acid: isolated from Siphonostegia chinensis	11.54	42	1	quinic acid
phaselic acid phaselic acid: structure in first source	2.08	1	0	hydroxycinnamic acid
caffeic acid phenethyl ester phenethyl caffeate : An alkyl caffeate ester in which 2-phenylethyl is the alkyl component.	3.57	8	0	alkyl caffeate ester	anti-inflammatory agent; antibacterial agent; antineoplastic agent; antioxidant; antiviral agent; immunomodulator; metabolite; neuroprotective agent
1,1-dimethylallyl caffeic acid ester 1,1-dimethylallyl caffeic acid ester: structure given in first source	2.1	1	0	hydroxycinnamic acid
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.	11.14	37	0	rosmarinic acid	geroprotector; plant metabolite
salvianolic acid a salvianolic acid A: a nootropic depside from Salvia miltiorrhizia	2.05	1	0	stilbenoid
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.	3.36	6	0	catechols; cinnamate ester; disaccharide derivative; glycoside; polyphenol	anti-inflammatory agent; antibacterial agent; antileishmanial agent; neuroprotective agent; plant metabolite
prunetin prunetin: reduces herpes virus-1 plaque formation. prunetin : A hydroxyisoflavone that is genistein in which the hydroxy group at position 7 is replaced by a methoxy group.	2.07	1	0	7-methoxyisoflavones; hydroxyisoflavone	anti-inflammatory agent; EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor; EC 1.3.1.22 [3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+))] inhibitor; 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.	2.07	1	0	aromatic ether; coumestans; delta-lactone; polyphenol	antineoplastic agent; apoptosis inducer; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; hepatoprotective agent; metabolite
rottlerin rottlerin: an angiogenesis inhibitor; an inhibitor of protein kinase Cdelta (PKCdelta) and calmodulin kinase III; RN refers to (E)-isomer; do not confuse this chalcone with an anthraquinone that is also called rottlerin (RN 481-72-1);. rottlerin : A chromenol that is 2,2-dimethyl-2H-chromene substituted by hydroxy groups at positions 5 and 7, a 3-acetyl-2,4,6-trihydroxy-5-methylbenzyl group at position 6 and a (1E)-3-oxo-1-phenylprop-1-en-3-yl group at position 8. A potassium channel opener, it is isolated from Mallotus philippensis.	2.07	1	0	aromatic ketone; benzenetriol; chromenol; enone; methyl ketone	anti-allergic agent; antihypertensive agent; antineoplastic agent; apoptosis inducer; K-ATP channel agonist; metabolite
ellagic acid [no description available]	7.02	24	1	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
7-hydroxyflavone 7-hydroxyflavone : A hydroxyflavonoid in which the flavone nucleus is substituted at position 7 by a hydroxy group.	2.49	2	0	hydroxyflavonoid
prostaglandin a1 [no description available]	2.07	1	0	prostaglandins A
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.	7.31	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.	2.07	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.	3.97	12	0	beta-D-glucoside; kaempferol O-glucoside; monosaccharide derivative; trihydroxyflavone	plant metabolite; trypanocidal drug
rhoifolin rhoifolin: from many plants. apigenin 7-O-neohesperidoside : An apigenin derivative having an alpha-(1->2)-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety attached to the 7-hydroxy group.	2.07	1	0	dihydroxyflavone; glycosyloxyflavone; neohesperidoside	metabolite
vitexin rhamnoside 2''-O-rhamnopyranosylvitexin: has both analgesic and anti-inflammatory activities; isolated from Alternanthera maritima; structure in first source. vitexin 2''-O-alpha-L-rhamnoside : A derivative of vitexin having an alpha-L-rhamnosyl residue attached at the 2''-position of the glucitol moiety.	2.54	2	0	C-glycosyl compound; disaccharide derivative; trihydroxyflavone	plant metabolite
veronicastroside veronicastroside: a flavonoid; second source Yak. Zas. shows same melting point, absorption, Rf and color tests for lonicerin (luteolin-7-rhamnoglucoside from Lonicera) and veronicastroside (luteolin-7-neohesperidoside from Trachelospermum);. luteolin 7-O-neohesperidoside : A disaccharide derivative that is luteolin substituted by a 2-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	2.07	1	0	disaccharide derivative; glycosyloxyflavone; neohesperidoside; trihydroxyflavone	antibacterial agent; metabolite
quercimeritrin quercimeritrin: from Rumex luminiastrum. quercetin 7-O-beta-D-glucoside : A quercetin O-glucoside in which a glucosyl residue is attached at position 7 of quercetin via a beta-glycosidic linkage.	3.03	1	0	beta-D-glucoside; flavonols; monosaccharide derivative; quercetin O-glucoside; tetrahydroxyflavone	antioxidant; metabolite
domoic acid domoic acid: kainic acid analog, heterocyclic amino acid from seaweed; RN given refers to parent cpd; structure. domoic acid : An L-proline derivative that is L-proline substituted by a carboxymethyl group at position 3 and a 6-carboxyhepta-2,4-dien-2-yl group at position 4. It is produced by the diatomic algal Pseudo-nitzschia. It is an analogue of kainic acid and a neurotoxin which causes amnesic shellfish poisoning (ASP).	2.07	1	0	L-proline derivative; non-proteinogenic L-alpha-amino acid; pyrrolidinecarboxylic acid; tricarboxylic acid	algal metabolite; hapten; marine metabolite; neuromuscular agent; neurotoxin
8-epi-prostaglandin f2alpha 8-epi-prostaglandin F2alpha: a potent preglomerular vasoconstrictor acting principally through thromboxane A2 receptor activation. 8-epi-prostaglandin F2alpha : An isoprostane that is prostaglandin F2alpha having inverted stereochemistry at the 8-position.	4.7	3	2	F2-isoprostane	biomarker; bronchoconstrictor agent; vasoconstrictor agent
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
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.	3.53	2	0	retinoic acid	antineoplastic agent; keratolytic drug; teratogenic agent
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.	2.08	1	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.	2.55	2	0	4-hydroxynon-2-enal; 4-hydroxynonenal
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	2.21	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]	3.1	1	0	morphinane alkaloid; organic heteropentacyclic compound	antitussive; drug allergen; environmental contaminant; opioid analgesic; opioid receptor agonist; prodrug; xenobiotic
cyclosporine ramihyphin A: one of the metabolites produced by Fusarium sp. S-435; RN given refers to cpd with unknown MF	2.07	1	0	homodetic cyclic peptide	anti-asthmatic drug; anticoronaviral agent; antifungal agent; antirheumatic drug; carcinogenic agent; dermatologic drug; EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; geroprotector; immunosuppressive agent; metabolite
methyl linoleate [no description available]	2.05	1	0	fatty acid methyl ester	plant metabolite
phenylethyl 3-methylcaffeate phenylethyl 3-methylcaffeate: a caffeic acid ester present in propolis, a natural resin produced by honey bees; structure given in first source	2.1	1	0
natamycin [no description available]	2.07	1	0	antibiotic antifungal drug; dicarboxylic acid monoester; epoxide; macrolide antibiotic; monosaccharide derivative; polyene antibiotic	antifungal agrochemical; antimicrobial food preservative; apoptosis inducer; bacterial metabolite; ophthalmology drug
quercetin [no description available]	2.13	1	0
rutin sulfate rutin sulfate: RN refers to Na salt	1.99	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	2.39	2	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
oleyl alcohol oleyl alcohol: structure; RN given refers to cpd without isomeric designation	7.6	1	0	fatty alcohol 18:1; long-chain primary fatty alcohol	metabolite; nonionic surfactant
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.	3.51	2	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.	3.1	1	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.	2.07	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
brefeldin a [no description available]	2.07	1	0	macrolide antibiotic	Penicillium metabolite
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.	3.82	3	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
fluticasone Fluticasone: A STEROID with GLUCOCORTICOID RECEPTOR activity that is used to manage the symptoms of ASTHMA; ALLERGIC RHINITIS, and ATOPIC DERMATITIS.. fluticasone : A trifluorinated corticosteroid used in the form of its propionate ester for treatment of allergic rhinitis.	4.8	1	1	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 3-oxo-Delta(4) steroid; corticosteroid; fluorinated steroid; thioester	anti-allergic agent; anti-asthmatic drug
benzyloxycarbonyl-phe-ala-fluormethylketone cathepsin B inhibitor : A cysteine protease inhibitor which inhibits cathepsin B (EC 3.4.22.1).	2.31	1	0
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.	2.15	1	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.	2.46	2	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
vinorelbine [no description available]	2.07	1	0	acetate ester; methyl ester; organic heteropentacyclic compound; organic heterotetracyclic compound; ring assembly; vinca alkaloid	antineoplastic agent; photosensitizing agent
10-hydroxy-2-decenoic acid (E)-10-hydroxydec-2-enoic acid : An omega-hydroxy amino acid that is 2-decenoic acid in which one of the hydrogens attached to the terminal carbon is replaced by a hydroxy group and in which the C=C double bond has E configuration. It is a component of royal jelly.	2.05	1	0	alpha,beta-unsaturated monocarboxylic acid; hydroxy monounsaturated fatty acid; omega-hydroxy-medium-chain fatty acid; straight-chain fatty acid	animal metabolite; geroprotector
casticin casticin: from fruit of Vitex rotundifolia; structure in second source. casticin : A tetramethoxyflavone that consists of quercetagetin in which the hydroxy groups at positions 3, 6, 7 and 4' have been replaced by methoxy groups. It has been isolated from Eremophila mitchellii.	2.1	1	0	dihydroxyflavone; tetramethoxyflavone	apoptosis inducer; plant metabolite
bilobetin bilobetin: a phospholipase A2 antagonist	2.31	1	0	flavonoid oligomer
bisdemethoxycurcumin curcumin III: structure in first source. bisdemethoxycurcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by 4-hydroxycinnamoyl groups.	2.47	2	0	beta-diketone; diarylheptanoid; enone; polyphenol	EC 3.2.1.1 (alpha-amylase) inhibitor; metabolite
centaureidin centaureidin: structure given in first source; isolated from Tanacetum microphyllum, Brickellia veronicaefolia. centaureidin : A trihydroxyflavone that consists of quercetagetin in which the hydroxy groups at positions 3, 6 and 4' have been replaced by methoxy groups. It has been isolated from Eremophila mitchellii and Athroisma proteiforme.	2.01	1	0	trihydroxyflavone; trimethoxyflavone	antineoplastic agent; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; plant metabolite
isochlorogenic acid [no description available]	6.51	31	0	quinic acid
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).	3.53	2	0	cinnamyl alcohol	plant metabolite
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.	2.58	2	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.	4.49	8	0	beta-D-glucoside; dimethoxybenzene; monosaccharide derivative; primary alcohol	hepatoprotective agent; plant metabolite
linarin linarin: flavone glycoside isolated from leaves of Linaria japonica MIQ	3.48	7	0
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.	3.13	5	0	alkyl caffeate ester; ethyl ester; hydroxycinnamic acid	anti-inflammatory agent; antineoplastic agent; metabolite
eupatin eupatin : A trimethoxyflavone that is quercetagetin methylated at positions 4', 6 and 7.	2.41	1	0	flavonols; trihydroxyflavone; trimethoxyflavone
fumarprotocetraric acid fumarprotocetraric acid: RN given refers to (E)-isomer; structure given in first source	1.99	1	0	carbonyl compound
andrographolide [no description available]	2.81	3	0	carbobicyclic compound; gamma-lactone; labdane diterpenoid; primary alcohol; secondary alcohol	anti-HIV agent; anti-inflammatory drug; antineoplastic agent; metabolite
isofraxidin isofraxidin: also see fraxidin	9.08	4	0	hydroxycoumarin
isomangiferin isomangiferin: structure given in first source. isomangiferin : A member of the class of xanthones that is 9H-xanthen-9-one substituted by hydroxy groups at positions 1, 3, 6 and 7 and a 1,5-anhydro-D-glucitol moiety at position 1.	2.42	2	0	C-glycosyl compound; polyphenol; xanthones	anti-HSV-1 agent; plant metabolite
isorhamnetin 3-o-glucoside isorhamnetin 3-O-glucoside: from the flowers of Persea gratissima; structure in first source. isorhamnetin 3-O-beta-D-glucopyranoside : A glycosyloxyflavone that is isorhamnetin substituted at position 3 by a beta-D-glucosyl residue.	4.25	6	0	beta-D-glucoside; glycosyloxyflavone; monomethoxyflavone; monosaccharide derivative; trihydroxyflavone	metabolite
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.	3.71	9	0	disaccharide derivative; kaempferol O-glucoside; rutinoside; trihydroxyflavone	metabolite; plant metabolite; radical scavenger
Kumatakenin [no description available]	3.35	1	0	ether; flavonoids
icariin [no description available]	2.49	2	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	2.25	1	0	butenolide	metabolite
martynoside martynoside: isolated from Verbena bipinnatifida Nutt; structure in first source	2.03	1	0
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.	2.08	1	0	4-coumaric acid methyl ester
methyl linolenate [no description available]	2.05	1	0	fatty acid methyl ester	insect attractant; plant metabolite
neoisoliquiritin neoisoliquiritin: inhibits angiogenesis; isolated from licorice root; isoliquiritin is the (E)-isomer; structure in first source; isoliquiritin is also available	2.55	2	0	flavonoids; glycoside
octadecyl caffeate caffeic acid n-octadecyl ester: isolated from Daphne acutiloba Rehd; structure in first source	2.07	1	0
artemetin [no description available]	3.35	1	0	ether; flavonoids
salazinic acid salazinic acid: lichen metabolite; structure in first source	1.99	1	0
tiliroside tiliroside: isolated from seeds of Eremocarpus setigerus	2.51	2	0	cinnamate ester; glycosyloxyflavone; monosaccharide derivative; trihydroxyflavone	plant metabolite
spiraeoside spiraeoside: from flowers of Filipendula ulmaria (L.); structure given in first source. quercetin 4'-O-beta-D-glucopyranoside : A quercetin O-glucoside that is quercetin with a beta-D-glucosyl residue attached at position 4'.	2.07	1	0	beta-D-glucoside; flavonols; monosaccharide derivative; quercetin O-glucoside; tetrahydroxyflavone	antineoplastic agent; antioxidant; plant metabolite
atractylenolide i atractylenolide I: from Atractylodes macrocephala Koidz; structure in first source	2.08	1	0
thunberginol a thunberginol A: isolated from Hydrangeae dulcis folium; structure given in first source	2.25	1	0
5,7,2'-trihydroxyflavone 5,7,2'-trihydroxyflavone: has inhibitory effects on the EBV-EA activation & on mouse skin tumor promotion in an in vivo two-stage carcinogenesis test; from Scutellaria baicalensis; structure given in first source	2.25	1	0	flavones
5-hydroxy-3,3',4',7-tetramethoxyflavone 5-hydroxy-3,7,3',4'-tetramethoxyflavone: from the rhizome of Kaempferia parviflora; inhibits monocyte adhesion and cellular reactive oxygen species production in human umbilical vein endothelial cells. 5-hydroxy-3,3',4',7-tetramethoxyflavone : A monohydroxyflavone that is 5-hydroxyflavone which is substituted by methoxy groups at positions 3,3',4' and 7.	2.52	2	0	3'-methoxyflavones; monohydroxyflavone; tetramethoxyflavone	plant metabolite
lead Lead: A soft, grayish metal with poisonous salts; atomic number 82, atomic weight 207.2, symbol Pb.	3.36	6	0	carbon group element atom; elemental lead; metal atom	neurotoxin
butylidenephthalide butylidenephthalide: structure in first source. (Z)-3-butylidenephthalide : A gamma-lactone that is phthalide substituted by a butylidene group at position 3. Isolated from Ligusticum porteri, it exhibits hypoglycemic activity.	3.18	1	0	isobenzofuranone
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)	1.99	1	0
13-hydroperoxy-9,11-octadecadienoic acid 13-hydroperoxy-9,11-octadecadienoic acid: RN given refers to (E,Z)-isomer; RN for unspecified isomer not in Chemline 8/12/83. 13-HPODE : An HPODE (hydroperoxyoctadecadienoic acid) in which the double bonds are at positions 9 and 11 (E and Z geometry, respectively) and the hydroperoxy group is at position 13.	2.01	1	0	hydroperoxy polyunsaturated fatty acid; octadecadienoic acid
6,7-dihydroxyflavone 6,7-dihydroxyflavone: intensifies effect of antibiotics on Staphylococcus aureus; structure in first source	2.07	1	0
(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.	2.07	1	0	dihydroxy monocarboxylic acid; indoles; organofluorine compound
flavokawain a flavokawain A: from kava extract, induces apoptosis in bladder cancer cells; structure in first source	2.07	1	0	chalcones
flavokawain b flavokawain B: from Piper methysticum Forst (Kava Kava) roots; structure in first source. flavokawain B : A member of the class of chalcones that consists of trans-chalcone substituted by hydroxy group at positions 2' and methoxy groups at positions 4' and 6'. Isolated from Piper methysticum and Piper rusbyi, it exhibits antileishmanial, anti-inflammatory and antineoplastic activities.	2.07	1	0	chalcones; dimethoxybenzene; phenols	anti-inflammatory agent; antileishmanial agent; antineoplastic agent; apoptosis inducer; metabolite
trimethyltin trimethyltin : An organotin compound that consists of stannane in which three of the four hydrogens are substituted by methyl groups.	2.13	1	0
aluminum Aluminum: A metallic element that has the atomic number 13, atomic symbol Al, and atomic weight 26.98.	8.24	5	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.	4.8	1	1	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.	4.8	1	1	metal atom; pnictogen
thallium Thallium: A heavy, bluish white metal, atomic number 81, atomic weight [204.382; 204.385], symbol Tl.. thallium : A metallic element first identified and named from the brilliant green line in its flame spectrum (from Greek thetaalphalambdalambdaomicronsigma, a green shoot).	2.31	1	0	boron group element atom
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)	2.76	2	0	metalloid atom; pnictogen	micronutrient
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.	3.55	2	0	cyclopropanes; morphinane-like compound; organic heteropentacyclic compound	antidote to opioid poisoning; central nervous system depressant; environmental contaminant; mu-opioid receptor antagonist; xenobiotic
indinavir sulfate Indinavir: A potent and specific HIV protease inhibitor that appears to have good oral bioavailability.	2.31	1	0	dicarboxylic acid diamide; N-(2-hydroxyethyl)piperazine; piperazinecarboxamide	HIV protease inhibitor
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.	10.82	6	1	chalcogen; nonmetal atom	macronutrient
methylazoxymethanol acetate Methylazoxymethanol Acetate: The aglycone of CYCASIN. It acts as a potent carcinogen and neurotoxin and inhibits hepatic DNA, RNA, and protein synthesis.	6.96	1	0	azoxy compound
kavain [no description available]	2.07	1	0	racemate	glycine receptor antagonist
2-Phenylethyl 3-phenyl-2-propenoate [no description available]	2.49	2	0	cinnamate ester
indolylacryloylglycine indolylacryloylglycine: chromogen found in urine; RN given refers to cpd without isomeric designation	2.07	1	0	N-acyl-amino acid
n-(4-hydroxy-beta-phenethyl)-4-hydroxycinnamide trans-N-p-coumaroyl tyramine: from the twigs of Celtis chinensis; structure in first source	2.05	1	0	hydroxycinnamic acid	metabolite
abscisic acid, (+,-)-isomer 2-cis-abscisic acid : A member of the class of abscisic acids in which the double bond betweeen positions 2 and 3 has cis- (natural) geometry.	2.07	1	0	abscisic acids	abscisic acid receptor agonist
jaceosidin jaceosidin : A trihydroxyflavone that is flavone with hydroxy groups at positions 5, 7 and 4' and methoxy groups at positions 3' and 6. Isolated from Salvia tomentosa and Artemisia asiatica, it exhibits anti-allergic, anti-inflammatory and apoptosis inducing activties.	3.65	2	0	dimethoxyflavone; trihydroxyflavone	anti-allergic agent; anti-inflammatory agent; antineoplastic agent; apoptosis inducer; metabolite
veratrine Veratrine: A voltage-gated sodium channel activator.	2.07	1	0	alkaloid
puerarin [no description available]	2.63	2	0	C-glycosyl compound; isoflavonoid
vinblastine sulfate [no description available]	2.07	1	0
catharanthine [no description available]	2.07	1	0	alkaloid ester; bridged compound; methyl ester; monoterpenoid indole alkaloid; organic heteropentacyclic compound; tertiary amino compound
cytochalasin e cytochalasin E: structure	2.07	1	0	cytochalasan alkaloid	metabolite
cytochalasin d [no description available]	2.07	1	0
hispanolone hispanolone: structure in first source	3.35	1	0
sinomenine sinomenine: isolated from root of Sinomenium acutum; antirheumatic, antineuralgic	2.45	2	0	morphinane alkaloid
ecdysterone Ecdysterone: A steroid hormone that regulates the processes of MOLTING or ecdysis in insects. Ecdysterone is the 20-hydroxylated ECDYSONE.. 20-hydroxyecdysone : An ecdysteroid that is ecdysone substituted by a hydroxy group at position 20.	2.07	1	0	14alpha-hydroxy steroid; 20-hydroxy steroid; 22-hydroxy steroid; 25-hydroxy steroid; 2beta-hydroxy steroid; 3beta-sterol; ecdysteroid; phytoecdysteroid	animal metabolite; plant metabolite
fumarates Fumarates: Compounds based on fumaric acid.. fumarate(2-) : A C4-dicarboxylate that is the E-isomer of but-2-enedioate(2-)	2.13	1	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.	2.08	1	0	monocarboxylic acid anion	Saccharomyces cerevisiae metabolite
bleomycin [no description available]	2.07	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.	4.18	17	0	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].	7.53	2	0	carbon group element atom; metalloid atom; nonmetal atom
phosphorus Phosphorus: A non-metal element that has the atomic symbol P, atomic number 15, and atomic weight 31. It is an essential element that takes part in a broad variety of biochemical reactions.	2.17	1	0	monoatomic phosphorus; nonmetal atom; pnictogen	macronutrient
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.	2.91	4	0	boron group element atom; metalloid atom; nonmetal atom	micronutrient
normorphine normorphine: RN given refers to (5 alpha,6 alpha)-isomer	3.1	1	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	4.55	22	0
bakuchiol bakuchiol: chief component of Psoralea corylifolia Linn; structure	2.54	2	0
zerumbone zerumbone: RN given for (E,E,E)-isomer; structure in first source. zerumbone : A sesquiterpenoid and cyclic ketone that is (1E,4E,8E)-alpha-humulene which is substituted by an oxo group at the carbon atom attached to two double bonds. It is obtained by steam distillation from a type of edible ginger, Zingiber zerumbet Smith, grown particularly in southeast Asia.	2.07	1	0	cyclic ketone; sesquiterpenoid	anti-inflammatory agent; glioma-associated oncogene inhibitor; plant metabolite
artepillin c artepillin C: RN refers to (E)-isomer	2.77	3	0
cinanserin Cinanserin: A serotonin antagonist with limited antihistaminic, anticholinergic, and immunosuppressive activity.. cinanserin : An aryl sulfide that is (2E)-3-phenyl-N-(2-sulfanylphenyl)prop-2-enamide in which the hydrogen of the thiol group is substituted by a 3-(dimethylamino)propyl group. It is a 5-hydroxytryptamine receptor antagonist and an inhibitor of SARS-CoV replication.	2.31	1	0	aryl sulfide; cinnamamides; secondary carboxamide; tertiary amino compound	anticoronaviral agent; antiviral agent; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor
solanesol solanesol : A nonaprenol that is hexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-ol substituted by 9 methyl groups at positions 3, 7, 11, 15, 19, 23, 27, 31 and 35 (the all-trans0stereoisomer).	2.07	1	0	nonaprenol; primary alcohol	plant metabolite
ceftriaxone [no description available]	2.07	1	0	1,2,4-triazines; 1,3-thiazoles; cephalosporin; oxime O-ether	antibacterial drug; drug allergen; EC 3.5.2.6 (beta-lactamase) inhibitor
guajavarin guajavarin: from leaves of Psidium guajava	2.53	2	0
narcissin flavonol narcissin flavonol: flavanol glycoside from Strumpfia maritima; do not confuse with other narcissin in Chemline, an alkaloid (lycorine (NM))	3.18	5	0	disaccharide derivative; glycosyloxyflavone; monomethoxyflavone; trihydroxyflavone
naltrindole benzofuran naltrindole benzofuran: structure given in first source	3.1	1	0	morphinane alkaloid
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.	2.06	1	0	disaccharide derivative; quercetin O-glucoside; tetrahydroxyflavone	antioxidant; plant metabolite
citrusinine i citrusinine I: acridone alkaloid isolated from Rutaceae	2.04	1	0	acridines
vitexin rhamnoside vitexin rhamnoside: an apigenin	2.07	1	0	flavonoids; glycoside
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.	2.53	2	0	alpha-L-arabinofuranoside; monosaccharide derivative; quercetin O-glycoside; tetrahydroxyflavone	hepatoprotective agent; plant metabolite
naltrindole naltrindole: delta opioid receptor antagonist	3.1	1	0	isoquinolines
(1S,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-[oxo-(3,4,5-trimethoxyphenyl)methoxy]-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylic acid methyl ester [no description available]	2.07	1	0	yohimban alkaloid
guanabenz Guanabenz: An alpha-2 selective adrenergic agonist used as an antihypertensive agent.	2.07	1	0	dichlorobenzene
famotidine [no description available]	2	1	0	1,3-thiazoles; guanidines; sulfonamide	anti-ulcer drug; H2-receptor antagonist; P450 inhibitor
abscisic acid Abscisic Acid: Abscission-accelerating plant growth substance isolated from young cotton fruit, leaves of sycamore, birch, and other plants, and from potatoes, lemons, avocados, and other fruits.. (S)-2-trans-abscisic acid : A 2-trans-abscisic acid with (S)-configuration at the chiral centre.. (+)-abscisic acid : The naturally occurring (1'S)-(+) enantiomer of abscisic acid. It is an important sesquiterpenoid plant hormone which acts as a regulator of plant responses to environmental stresses such as drought and cold.	2.77	3	0	2-trans-abscisic acid
n-caproylsphingosine N-(hexanoyl)sphing-4-enine : An N-acylsphingosine consisting of sphing-4-enine bearing a hexanoyl group on nitrogen.	2.07	1	0	N-acylsphingosine
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.	2.07	1	0	beta-D-glucoside; monosaccharide derivative; steroid saponin	plant metabolite
quercetin-3'-o-beta-d-glucopyranoside quercetin 3'-O-glucoside: structure in first source	2.79	3	0
germacrene a germacrene A: RN given for (S-(E,E))-isomer; structure in first source	2.02	1	0	germacrene; sesquiterpene
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.	2.63	2	0	ethyl ester; isoindoles; monochlorobenzenes	herbicide
benzyl caffeate benzyl caffeate: isolated from Liaoxi propolis	2.49	2	0
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.	1.97	1	0	ammonium salt; inorganic sulfate salt	fertilizer
caffeoyl-coenzyme a caffeoyl-coenzyme A: structure given in first source	2.74	3	0
caffeoylmalic acid caffeoylmalic acid: from extracts of Chelidonium majus & Corydalis lutea	2.47	2	0	hydroxycinnamic acid
N-[(5-methyl-1,2-oxazol-3-yl)carbonyl]-L-alanyl-L-valyl-N-{(2S,3E)-5-(benzyloxy)-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide N-[(5-methyl-1,2-oxazol-3-yl)carbonyl]-L-alanyl-L-valyl-N-{(2S,3E)-5-(benzyloxy)-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide : A tripeptide resulting from the formal condensation of the carboxy group of N-[(5-methyl-1,2-oxazol-3-yl)carbonyl]-L-alanyl-L-valine with the amino group of benzyl (2E,4S)-4-(L-leucylamino)-5-[(3S)-2-oxopyrrolidin-3-yl]pent-2-enoate. It is an inhibitor of the main protease of SARS-CoV-2.	2.31	1	0	benzyl ester; isoxazoles; pyrrolidin-2-ones; tripeptide	anticoronaviral agent; antiviral agent; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor
monorden monorden: inhibits HSP90 Heat-Shock Proteins, DNA topoisomerase VI and human Topoisomerase II	2.07	1	0	cyclic ketone; enone; epoxide; macrolide antibiotic; monochlorobenzenes; phenols	antifungal agent; metabolite; tyrosine kinase inhibitor
ginkgolide b [no description available]	2.48	2	0
ro 42-5892 remikiren : An L-histidine derivative that is L-histidine in which one of the amino hydrogens is replaced by a (2S)-2-[(2-methylpropane-2-sulfonyl)methyl]-3-phenylpropanoyl group and the carboxy group is replaced by a [(2S,3R,4S)-1-cyclohexyl-4-cyclopropyl-3,4-dihydroxybutan-2-yl]amino group. It is a renin inhibitor which was under development for the treatment of hypertension (now discontinued).	2.07	1	0	cyclopropanes; diol; L-histidine derivative; secondary carboxamide; sulfone	antihypertensive agent; EC 3.4.23.15 (renin) inhibitor; peptidomimetic; vasodilator agent
quercetin-3-o-alpha-l-rhamnopyranoside quercetin-3-O-alpha-L-rhamnopyranoside: from Rhododendron ovatum Planch; structure in first source	2.17	1	0
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.	2.58	2	0	chalcogen; nonmetal atom	micronutrient
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.	2.41	2	0
homatropine hydrobromide, (endo-(+-)-isomer) [no description available]	2.07	1	0
hydrocotarnine hydrobromide [no description available]	2.07	1	0
salsolinol hydrobromide [no description available]	2.07	1	0
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.	2.11	1	0	maleate salt; tetracyclic antidepressant	anaesthetic; anticonvulsant; neuroprotective agent; nicotinic antagonist; NMDA receptor antagonist
lasalocid sodium lasalocid sodium : The sodium salt of lasalocid. It is a veterinary ionophore antibiotic used for prevention and treatment of coccidiosis in poultry.	2.07	1	0	benzoates; organic sodium salt	coccidiostat; ionophore
tiacrilast tiacrilast: structure given in first source	2.07	1	0
sclerotiorin sclerotiorin: isolated from monoverticillate Penicillia; RN given for (R-(R,S-(E,E)))-isomer; structure in first source	2.07	1	0	azaphilone
himbacine himbacine: muscarine receptor antagonist; RN given refers to (3S-(3alpha,3aalpha,4beta(1E,2(2R,6S)),4abeta,8aalpha,9aalpha))-isomer; structure given in first source. himbacine : A piperidine alkaloid that is decahydronaphtho[2,3-c]furan-1(3H)-one substituted by a methyl group at position 3 and a 2-[(2R,6S)-1,6-dimethylpiperidin-2-yl]ethenyl group at position 4. It has been isolated from the bark of Australian magnolias.	2.07	1	0	gamma-lactone; organic heterotricyclic compound; piperidine alkaloid	muscarinic antagonist
ebelactone b ebelactone B: esterase inhibitor; structure given in first source; see also ebelactone A	2.07	1	0
(2e,4e,6e,10e)-3,7,11,15-tetramethyl-2,4,6,10,14-hexadecapentaenoic acid (2E,4E,6E,10E)-3,7,11,15-tetramethyl-2,4,6,10,14-hexadecapentaenoic acid: an acyclic retinoid that suppresses hepatocellular carcinoma recurrence; structure in first source	1.97	1	0
3-o-methylbutein 3-O-methylbutein: RN given refers to (E)-isomer; structure given in first source	2.07	1	0	chalcones
thermozymocidin thermozymocidin: a serine palmitoyltransferase inhibitor; FTY720 is an analog	2.07	1	0	alpha-amino fatty acid; hydroxy monocarboxylic acid; non-proteinogenic alpha-amino acid; sphingoid	antifungal agent; antimicrobial agent; antineoplastic agent; apoptosis inducer; EC 2.3.1.50 (serine C-palmitoyltransferase) inhibitor; fungal metabolite; immunosuppressive agent
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	2.07	1	0
tussilagone tussilagone: an oplopanone type saturated indene sesquiterpene; platelet activating factor antagonist	2.08	1	0
kyn 54 KYN 54: structure given in first source; a novel synthesized retinoid; potential chemopreventive agent for intestinal neoplasm	1.99	1	0
4-coumaroyl-coenzyme a 4-coumaroyl-coenzyme A: structure given in first source. trans-4-coumaroyl-CoA : A 4-coumaroyl-CoA in which the double bond of the coumaroyl group has trans-geochemistry.. 4-coumaroyl-CoA : The S-(4-coumaroyl) derivative of coenzyme A.	2.08	1	0	4-coumaroyl-CoA
drupanin Drupanin: anti-oxidant and anti-cancer; structure in first source	2.07	1	0
caftaric acid [no description available]	8.79	10	0	hydroxycinnamic acid
marein marein: hypoglycemic from Coreopsis tinctoria; structure in first source	2.81	3	0	flavonoids; glycoside
2-coumaroylquinic acid 2-coumaroylquinic acid: precursor of chlorogenic acid & metabolite of cinnamic acid in Cestrum Poep gii, a plant; RN in Chemline for (5beta)-isomer: 1899-30-5; structure. 5-p-coumaroylquinic acid : A cinnamate ester obtained by formal condensation of the carboxy group of 4-coumaric acid with the 5-hydroxy group of (-)-quinic acid.. trans-5-O-(4-coumaroyl)-D-quinic acid : The 5-O-(4-coumaroyl) derivative of (-)-quinic acid.	3.18	5	0	quinic acid
coniferyl ferulate coniferyl ferulate: found in the rhizome of Cnidium officinale Makino; structure given in first source; RN given refers to cpd without isomeric designation	2.25	1	0
bifenthrin bifenthrin: a type I pyrethroid. bifenthrin : A carboxylic ester obtained by formal condensation of cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylic acid and [(2-methyl-1,1'-biphenyl)-3-yl]methanol.. kappa-bifenthrin : A carboxylic ester obtained by formal condensation of the carboxy group of (1R,3R)-3-[(1Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropanecarboxylic acid with the hydroxy group of [(2-methyl-1,1'-biphenyl)-3-yl]methanol.	2.13	1	0	carboxylic ester; cyclopropanecarboxylate ester; cyclopropanes; organochlorine compound; organofluorine compound	pyrethroid ester acaricide; pyrethroid ester insecticide
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	7.78	3	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
trilobatin trilobatin: anti-inflammatory from Lithocarpus polystachyus leaves; structure in first source. trilobatin : An aryl beta-D-glucoside that is phloretin attached to a beta-D-glucopyranosyl residue at position 4' via a glycosidic linkage. It is isolated from the leaves of the Chinese sweet tea Lithocarpus polystachyus and exhibits significant anti-hyperglycemic, anti-oxidative and anti-inflammatory properties.	3.27	1	0	aryl beta-D-glucoside; dihydrochalcones; monosaccharide derivative	anti-inflammatory agent; antioxidant; plant metabolite; sweetening agent
19-hydroxycholesterol 19-hydroxycholesterol: structure given in first source	3.1	1	0	cholestanoid
4,5-di-O-caffeoylquinic acid [no description available]	3.43	7	0	quinic acid
indigo carmine 3,5-di-O-(E)-caffeoylquinic acid: from roots of Lychnophora ericoides; structure in first source. 3,5-di-O-caffeoyl quinic acid : A carboxylic ester that is the diester obtained by the condensation of the hydroxy groups at positions 3 and 5 of (-)-quinic acid with the carboxy group of trans-caffeic acid. Isolated from Brazilian propolis and Suaeda glauca, it exhibits hepatoprotective and cytotoxic activities.	7.09	74	1
methyl chlorogenate methyl chlorogenate: from Eriobotrya japonica; structure in first source	5.06	15	0	quinic acid
isoacteoside isoacteoside: a phenylethanoid glycoside isolated from Indian paintbrush (Verbenaceae) Castilleja linariaefolia; also in other plants; structure given in first source	2.13	1	0	hydroxycinnamic acid
Ethyl (E,4S)-4-[[(2S)-2-[[(2S)-3-methyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]-3-phenylpropanoyl]amino]-5-[(3S)-2-oxopyrrolidin-3-yl]pent-2-enoate [no description available]	2.31	1	0	dipeptide	anticoronaviral agent
clovamide clovamide: RN given for (Z)-isomer; structure in first source	2.08	1	0	tyrosine derivative
beta-escin [no description available]	6.92	20	1
borneol [no description available]	3.1	1	0	borneol
emetine hydrochloride [no description available]	2.01	1	0
hydroxyachillin hydroxyachillin: isolated from Tanacetum microphyllum; structure given in first source	2.46	2	0	gamma-lactone
nifurtimox Nifurtimox: A nitrofuran thiazine that has been used against TRYPANOSOMIASIS.	2.13	1	0	nitrofuran antibiotic
butylscopolammonium bromide Butylscopolammonium Bromide: Antimuscarinic quaternary ammonium derivative of scopolamine used to treat cramps in gastrointestinal, urinary, uterine, and biliary tracts, and to facilitate radiologic visualization of the gastrointestinal tract.	2.07	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.	2.02	1	0	isoquinoline alkaloid fundamental parent; morphinane alkaloid
mdl 201053 MDL 201053: Immunosuppressive Agent; RN given refers to compound with no isomeric designation	2.31	1	0
fumagillin [no description available]	2.07	1	0	antibiotic antifungal drug; carboxylic ester; dicarboxylic acid monoester; meroterpenoid; organooxygen heterocyclic antibiotic; spiro-epoxide	angiogenesis inhibitor; antibacterial drug; antimicrobial agent; antiprotozoal drug; fungal metabolite; methionine aminopeptidase 2 inhibitor
artesunate artesunic acid: RN given for (3R-(3alpha,5abeta,6beta,8abeta,9alpha,10alpha,12beta,(2aR*))-isomer; succinic ester of artemether	3.63	2	0	artemisinin derivative; cyclic acetal; dicarboxylic acid monoester; hemisuccinate; semisynthetic derivative; sesquiterpenoid	antimalarial; antineoplastic agent; ferroptosis inducer
ginsenoside rb2 [no description available]	2.1	1	0	12beta-hydroxy steroid; beta-D-glucoside; disaccharide derivative; ginsenoside; tetracyclic triterpenoid	antiviral agent; hypoglycemic agent; plant metabolite
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
anisodamine [no description available]	2.07	1	0
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.	4.32	5	0	beta-D-glucoside; rebaudioside; tetracyclic diterpenoid	sweetening agent
isoborneol isoborneol: RN given refers to cpd without isomeric designation; structure	2.41	1	0	borneol
5-Chloro-3-pyridinyl 2-furoate [no description available]	2.31	1	0	carboxylic ester	anticoronaviral agent
bufalin bufalin: cardiotonic; powerful anesthetic & one of the active constituents of the Chinese drug ch'an su(senso); in Japan prepared from skin of Bufo bufo garfarizans; RN given refers to (3beta,5beta)-isomer. bufalin : A 14beta-hydroxy steroid that is bufan-20,22-dienolide having hydroxy substituents at the 5beta- and 14beta-positions. It has been isolated from the skin of the toad Bufo bufo.	2.07	1	0	14beta-hydroxy steroid; 3beta-hydroxy steroid	animal metabolite; anti-inflammatory agent; antineoplastic agent; cardiotonic drug
hypericum Hypericum: Genus of perennial plants in the family CLUSIACEAE (sometimes classified as Hypericaceae). Herbal and homeopathic preparations are used for depression, neuralgias, and a variety of other conditions. Hypericum contains flavonoids; GLYCOSIDES; mucilage, TANNINS; volatile oils (OILS, ESSENTIAL), hypericin and hyperforin.. 6-formamidopenicillanic acid : A penicillanic acid having a (6R)-formamido substituent.	9.32	18	0	penicillanic acids
alpha-solanine [no description available]	2.07	1	0	glycoalkaloid; organic heterohexacyclic compound; steroid saponin; trisaccharide derivative	antineoplastic agent; apoptosis inducer; phytotoxin; plant metabolite
chlorhexidine Chlorhexidine: A disinfectant and topical anti-infective agent used also as mouthwash to prevent oral plaque.. chlorhexidine : A bisbiguanide compound with a structure consisting of two (p-chlorophenyl)guanide units linked by a hexamethylene bridge.	2	1	0	biguanides; monochlorobenzenes	antibacterial agent; antiinfective agent
3-O-feruloyl-D-quinic acid 3-O-feruloyl-D-quinic acid : A quinic acid that is the 3-O-feruloyl derivative of D-quinic acid.	2.07	1	0	enoate ester; quinic acid	plant metabolite
gw 311616 GW 311616: structure in first source	2.03	1	0
ginsenoside f1 ginsenoside F1: from ginseng. ginsenoside F1 : A ginsenoside found in Panax species that is dammarane which is substituted by hydroxy groups at the 3beta, 6alpha, 12beta and 20 pro-S positions, in which the hydroxy group at position 20 has been converted to the corresponding beta-D-glucopyranoside, and in which a double bond has been introduced at the 24-25 position.	2.1	1	0	12beta-hydroxy steroid; 3beta-hydroxy-4,4-dimethylsteroid; 3beta-hydroxy steroid; 6alpha-hydroxy steroid; beta-D-glucoside; ginsenoside; tetracyclic triterpenoid	apoptosis inhibitor; plant metabolite
bicyclol bicyclol: an antihepatitis drug, on the metabolism and hepatotoxicity of aflatoxin B1 (AFB1) in rats.	2.05	1	0
platyphylloside platyphylloside: from the bark of black alder, inhibits the growth of sensitive and multi-drug resistant non-small cell lung carcinoma cells; structure in first source	2.03	1	0
mumbaistatin mumbaistatin: inhibits glucose-6-phosphate translocase; isolated from Streptomyces sp.; structure in first source	2.05	1	0
apigenin-7-o-rutinoside [no description available]	2.07	1	0
gambogic acid gambogic acid: RN given refers to (1R-(1alpha,1(Z),3abeta,5alpha,11beta,14aS*))-isomer	2.07	1	0	pyranoxanthones	metabolite
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).	4.11	14	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
s 4048 S 4048: structure in first source	2	1	0
ginsenoside rb1 [no description available]	2.1	1	0	ginsenoside; glycoside; tetracyclic triterpenoid	anti-inflammatory drug; anti-obesity agent; apoptosis inhibitor; neuroprotective agent; plant metabolite; radical scavenger
sucrose monolaurate sucrose monolaurate: RN given refers to monolaurate	2.1	1	0
bn 52020 [no description available]	2.07	1	0
prunin protein, prunus naringenin-7-O-glucoside: from Dracocephalum rupestre; has protective effects against doxorubicin-induced apoptosis	2.13	1	0
sp 100030 N-(3,5-bis(trifluoromethyl)phenyl)-2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxamide: transcription factor inhibitor specific to T-cells	2.31	1	0
ginsenoside f2 ginsenoside F2: isolated from the leaves of Panax ginseng. ginsenoside F2 : 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-glucopyranosides, and in which a double bond has been introduced at the 24-25 position.	2.1	1	0	12beta-hydroxy steroid; beta-D-glucoside; ginsenoside; tetracyclic triterpenoid	antineoplastic agent; apoptosis inducer; plant metabolite
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.	2.57	2	0	ginsenoside; glycoside; tetracyclic triterpenoid	angiogenesis modulating agent; antineoplastic agent; apoptosis inducer; plant metabolite
sorbitan monooleate [no description available]	2.17	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.	3.1	1	0	morphinane alkaloid
rhodamine 123 [no description available]	2.07	1	0	organic chloride salt; xanthene dye	fluorochrome
tocotrienols tocotrienol : A tocol in which the hydrocarbon chain at position 2 contains three double bonds.	3.5	1	1	diterpenoid
gw0742 GW 610742: structure in first source	2.31	1	0	monocarboxylic acid
negundoside negundoside: an antioxidant irridiod glycoside from leaves of Vitex negundo; structure in first source	2.11	1	0
benzyloxycarbonyl-isoleucyl-glutamyl(o-tert-butyl)-alanyl-leucinal benzyloxycarbonyl-isoleucyl-glutamyl(O-tert-butyl)-alanyl-leucinal: inhibits chymotrypsin activity of the proteasome	2.31	1	0
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.	4.8	1	1
hypaconitine hypaconitine: RN given refers to the (1alpha,6alpha,14alpha,15alpha,16beta)-isomer	2.6	1	0
methyl 3,5-di-o-caffeoyl quinate 3,5-dicaffeoylquinic acid methyl ester: results suggest that the effect of 3,5-dicaffeoylquinic esters on CHS is associated with a decrease in the production of interleukins, but not with the inhibition of iNOS expression. Moreover, esterification of the carboxyl group at C-1 enhanced protection against tyrosine nitration in the skin. methyl 3,5-di-O-caffeoyl quinate : A methyl ester resulting from the formal condensation of the carboxy group of 3,5-di-O-caffeoyl quinic acid with methanol. Isolated from Suaeda glauca and Dichrocephala bicolor, it exhibits hepatoprotective activity.	4.38	7	0
bismuth tripotassium dicitrate bismuth tripotassium dicitrate: contains tripotassium di-citratobismuthate used in gastric & duodenal ulcer therapy; do not confuse with colloidal bismuth subnitrate	2.08	1	0
octyl caffeate octyl caffeate: an antioxidant; structure in first source	2.1	1	0
sepantronium sepantronium: a survivin suppressant with antineoplastic activity. sepantronium : An organic cation that is 1-(2-methoxyethyl)-2-methyl-1H-naphtho[2,3-d]imidazole-4,9-dione in which the nitrogen at position 3 of the napthoimidazole moiety has been alkylated by a pyrazin-2-ylmethyl group.	2.31	1	0	organic cation
delphinidin 3-sambubioside delphinidin 3-sambubioside: a Hibiscus anthocyanin that induces apoptosis in human leukemia cells through reactive oxygen species-mediated mitochondrial pathway. delphinidin 3-O-beta-D-sambubioside : An anthocyanidin 3-O-beta-D-sambubioside having delphinidin as the anthocyanidin component.	2.07	1	0	anthocyanidin 3-O-beta-D-sambubioside	apoptosis inducer; metabolite
carmine carminic acid : A tetrahydroxyanthraquinone that is that is 1,3,4,6-tetrahydroxy-9,10-anthraquinone substituted by a methyl group at position 8, a carboxy group at position 7 and a 1,5-anhydro-D-glucitol moiety at position 2 via a C-glycosidic linkage. It is a natural dye isolated from several insects such as Dactylopius coccus.	2.07	1	0	C-glycosyl compound; monocarboxylic acid; tetrahydroxyanthraquinone	animal metabolite; histological dye
gymnasterkoreayne b gymnasterkoreayne B: from Gymnaster koraiensis; structure in first source	2.08	1	0
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.	2.82	2	0
corchoionoside c corchoionoside C: structure given in first source; from leaves of Corchorus olitorius	2.11	1	0
n-(3-amino-1-(cyclobutylmethyl)-2,3-dioxopropyl)-3-(2-((((1,1-dimethylethyl)amino)carbonyl)amino)-3,3-dimethyl-1-oxobutyl)-6,6-dimethyl-3-azabicyclo(3.1.0)hexan-2-carboxamide boceprevir : A synthetic tripeptide consisting of N-(tert-butylcarbamoyl)-3-methyl-L-valyl, a cyclopropyl-fused prolyl and 3-amino-4-cyclobutyl-2-oxobutanamide residues joined in sequence. Used for treatment of chronic hepatitis C virus genotype 1 infection.	2.31	1	0	tripeptide; ureas	antiviral drug; hepatitis C protease inhibitor; peptidomimetic
2-hydroxyestriol 2-hydroxyestriol: structure	3.1	1	0
bavachinin bavachinin: do not confuse with bavachin	2.07	1	0	flavanones
triptohypol C triptohypol C : A pentacyclic triterpenoid with formula C29H40O4, originally isolated from the root bark of Tripterygium regelii.	2.31	1	0	benzenediols; monocarboxylic acid; pentacyclic triterpenoid	apoptosis inducer; plant metabolite
biapigenin biapigenin: bis-apigenin coupled at 3' & 3' positions; inhibits various cytochrome P450 enzymes; isolated from St. John's Wort	2.01	1	0	flavonoid oligomer
2,3-bis(3'-hydroxybenzyl)butyrolactone, (trans)-isomer [no description available]	2.1	1	0
ribose ribopyranose : The pyranose form of ribose.	2.54	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.	2.03	1	0	alpha-D-glucosyl-(1->4)-D-mannopyranose
Diosmetin 7-O-beta-D-glucopyranoside [no description available]	2.15	1	0	flavonoids; glycoside
grayanotoxin iii grayanotoxin III: from leaves of Leucothoe grayana (Ericaceae); RN refers to (3beta,6beta,14R)-isomer; structure given in first source	2.07	1	0
benzyl glucopyranoside benzyl glucopyranoside: structure in first source	2.02	1	0
bakkenolide b bakkenolide B: antineoplastic agent isolated from Petasites tatewakianus; structure in first source	2.25	1	0	terpene lactone
regorafenib [no description available]	7.17	1	0	(trifluoromethyl)benzenes; aromatic ether; monochlorobenzenes; monofluorobenzenes; phenylureas; pyridinecarboxamide	antineoplastic agent; hepatotoxic agent; tyrosine kinase inhibitor
2-(4-chlorophenyl)-1,2-benzothiazol-3-one [no description available]	2.31	1	0	benzothiazoles
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.	4.21	3	1	biflavonoid; hydroxyflavan; polyphenol; proanthocyanidin	anti-inflammatory agent; EC 3.4.21.5 (thrombin) inhibitor; metabolite
Phenylethyl beta-D-glucopyranoside [no description available]	3.03	1	0	glycoside
np 031112 tideglusib: an NSAID and neuroprotective agent. tideglusib : A member of the class of thiadiazolidines that is 1,2,4-thiadiazolidine-3,5-dione which is substituted by a naphthalen-1-yl group at position 2 and by a benzyl group at position 4. It is a non-ATP competitive inhibitor of glycogen synthase kinase 3beta (GSK3beta) and has neuroprotective effects. Currently under clinical investigation for the treatment of Alzheimer's disease and progressive supranuclear palsy.	2.31	1	0	benzenes; naphthalenes; thiadiazolidine	anti-inflammatory agent; apoptosis inducer; EC 2.7.11.26 (tau-protein kinase) inhibitor; neuroprotective agent
linoleic acid hydroperoxide linoleic acid hydroperoxide: RN refers to (Z,Z)-isomer. linoleic acid hydroperoxide : A HPODE that is a mono-hydroperoxy derivative of linoleic acid	2.01	1	0
Dihydrotanshinone I dihydrotanshinone I: extracted from Radix Salviae	2.54	2	0	abietane diterpenoid	anticoronaviral agent
dorsomorphin dorsomorphin: an AMPK inhibitor. dorsomorphin : A pyrazolopyrimidine that is pyrazolo[1,5-a]pyrimidine which is substituted at positions 3 and 6 by pyridin-4-yl and p-[2-(piperidin-1-yl)ethoxy]phenyl groups, respectively. It is a potent, selective, reversible, and ATP-competitive inhibitor of AMPK (AMP-activated protein kinase, EC 2.7.11.31) and a selective inhibitor of bone morphogenetic protein (BMP) signaling.	2.07	1	0	aromatic ether; piperidines; pyrazolopyrimidine; pyridines	bone morphogenetic protein receptor antagonist; EC 2.7.11.31 {[hydroxymethylglutaryl-CoA reductase (NADPH)] kinase} inhibitor
carfilzomib [no description available]	4.8	1	1	epoxide; morpholines; tetrapeptide	antineoplastic agent; proteasome inhibitor
mk-0893 [no description available]	2.31	1	0
chlorophyll b [no description available]	2.4	2	0	chlorophyll	cofactor
ginsenoside rd ginsenoside Rd: RN refers to (3beta,12beta)-isomer. ginsenoside Rd : A ginsenoside found in Panax ginseng and Panax japonicus var. major that is (20S)-ginsenoside Rg3 in which the hydroxy group at position 20 has been converted to its beta-D-glucopyranoside.	2.1	1	0	beta-D-glucoside; ginsenoside; tetracyclic triterpenoid	anti-inflammatory drug; apoptosis inducer; immunosuppressive agent; neuroprotective agent; plant metabolite; vulnerary
2-(n-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-2-deoxyglucose 2-(N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-2-deoxyglucose: fluorescent probe for glucose uptake activity in E coli; structure given in first source	2.04	1	0
empagliflozin [no description available]	4.8	1	1	aromatic ether; C-glycosyl compound; monochlorobenzenes; tetrahydrofuryl ether	hypoglycemic agent; sodium-glucose transport protein subtype 2 inhibitor
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.	2.07	1	0	benzoxazole
scopolamine hydrobromide [no description available]	2.9	2	0
asperulosidic acid asperulosidic acid: from the fruit juice of Morinda citrifolia (noni), a plant originally grown in the Hawaiian and Tahitian islands, has long been used by islanders to treat diseases, including cancer; structure in first source	2.13	1	0	glycoside; iridoid monoterpenoid
cinobufagin cinobufagin: isolated from Chinese medicinal preparation ch'an su; derived from toad venom	2.07	1	0	steroid lactone
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.	2.53	2	0
atropine sulfate [no description available]	2.07	1	0
cannogenin thevetoside cannogenin thevetoside: from Thevetia neriifolia; minor descriptor (75-84); on-line & Index Medicus search CARDENOLIDES (77-84), CARDANOLIDES (75-76); RN given refers to (3beta,5beta)-isomer	2.07	1	0	cardenolide glycoside
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)	2.52	2	0
ginsenoside rc [no description available]	2.1	1	0	12beta-hydroxy steroid; beta-D-glucoside; disaccharide derivative; ginsenoside; tetracyclic triterpenoid	hypoglycemic agent; plant metabolite
ginsenoside rb3 [no description available]	2.1	1	0	12beta-hydroxy steroid; beta-D-glucoside; disaccharide derivative; ginsenoside; tetracyclic triterpenoid	antidepressant; antioxidant; cardioprotective agent; neuroprotective agent; NMDA receptor antagonist; plant metabolite
acid phosphatase Acid Phosphatase: An enzyme that catalyzes the conversion of an orthophosphoric monoester and water to an alcohol and orthophosphate. EC 3.1.3.2.	2.15	1	0
1-deoxynojirimycin hydrochloride [no description available]	2.04	1	0
eriodictyol 7-O-beta-D-glucopyranoside [no description available]	2.07	1	0	beta-D-glucoside; flavanone glycoside; monosaccharide derivative; trihydroxyflavanone	plant metabolite; radical scavenger
benzoylhypaconine benzoylhypaconine: Aconitum alkaloid in serum. benzoylhypaconine : A diterpene alkaloid with formula C31H43NO9 that is isolated from several Aconitum species.	2.08	1	0
luteolin-7-o-glucuronide luteolin-7-O-glucuronide: from the leaves and flowers of the cannabinoid-free cannabis (Cannabis sativa subsp. sativa L., Cannabaceae); structure in first source	2.03	1	0
4,5-dicaffeoyl quinic acid 4,5-dicaffeoyl quinic acid: structure in first source	3.57	8	0
(3z,6alpha,7alpha)-isomer of 3-butylidene-4,5,6,7-tetrahydro-6,7-dihydroxy-1(3h)-isobenzofuranone senkyunolide H: from Ligusticum chuanxiong; structure nin first source	2.25	1	0	2-benzofurans
ludartin ludartin: a TRPA1 channel activator; structure in first source	3.35	1	0
hypocrellin a hypocrellin A: isolated from fungus Hypocrella bambusae sacc	2.07	1	0
lyoniside lyoniside: see also eleutherosides & syringin for eleutheroside B: 118-34-3; RN given refers to (3beta)-isomer	2.48	2	0
2',7'-dichlorodihydrofluorescein 2',7'-dichlorodihydrofluorescein: nonfluorescent, reduced form of 2',7'-dichlorofluorescein	2.06	1	0
cyclo[18]carbon cyclo[18]carbon : An allotrope of carbon with molecular formula C18 existing as a ring of eighteen carbon atoms, connected by alternating triple and single bonds.	2.21	1	0	carbocyclic compound; elemental carbon
2-aminoindan-2-phosphonic acid 2-aminoindan-2-phosphonic acid: inhibits salicylic acid synthesis	2.48	2	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.	3.03	4	0
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	2.1	1	0	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
Benzotriazol-1-yl 1H-indole-5-carboxylate [no description available]	2.31	1	0	indolyl carboxylic acid	anticoronaviral agent
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.	3.38	6	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).	3.78	2	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	2.25	1	0
vitisin a [no description available]	2.07	1	0	benzofurans
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.	2.04	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.	11.8	5	2	peptide hormone
beta-endorphin beta-Endorphin: A 31-amino acid peptide that is the C-terminal fragment of BETA-LIPOTROPIN. It acts on OPIOID RECEPTORS and is an analgesic. Its first four amino acids at the N-terminal are identical to the tetrapeptide sequence of METHIONINE ENKEPHALIN and LEUCINE ENKEPHALIN.. beta-endorphin : A polypeptide consisting of 31 amino acid residues in the sequence Tyr-Gly-Gly-Phe-Met-Thr-Ser-Glu-Lys-Ser-Gln-Thr-Pro-Leu-Val-Thr-Leu-Phe-Lys-Asn-Ala-Ile-Ile-Lys-Asn-Ala-Tyr-Lys-Lys-Gly-Glu. It is an endogenous opioid peptide neurotransmitter found in the neurons of both the central and peripheral nervous system and results from processing of the precursor protein proopiomelanocortin (POMC).	2.15	1	0
angiotensinogen Angiotensinogen: An alpha-globulin of about 453 amino acids, depending on the species. It is produced by the liver in response to lowered blood pressure and secreted into blood circulation. Angiotensinogen is the inactive precursor of the ANGIOTENSINS produced in the body by successive enzyme cleavages. Cleavage of angiotensinogen by RENIN yields the decapeptide ANGIOTENSIN I. Further cleavage of angiotensin I (by ANGIOTENSIN CONVERTING ENZYME) yields the potent vasoconstrictor octapeptide ANGIOTENSIN II; and then, via other enzymes, other angiotensins also involved in the hemodynamic-regulating RENIN-ANGIOTENSIN SYSTEM.	2.15	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.	14.95	53	4
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.	7.46	7	3
oritavancin oritavancin : A semisynthetic glycopeptide used (as its bisphosphate salt) for the treatment of acute bacterial skin and skin structure infections caused or suspected to be caused by susceptible isolates of designated Gram-positive microorganisms including MRSA.	2.31	1	0	disaccharide derivative; glycopeptide; semisynthetic derivative	antibacterial drug; antimicrobial agent
incretins Incretins: Peptides which stimulate INSULIN release from the PANCREATIC BETA CELLS following oral nutrient ingestion, or postprandially.	4.84	2	2
5-Bromopyridin-3-yl furan-2-carboxylate [no description available]	2.31	1	0	carboxylic ester	anticoronaviral agent
(5-Chloropyridin-3-yl) 1H-indole-5-carboxylate [no description available]	2.31	1	0	indolyl carboxylic acid	anticoronaviral agent
5-Chloropyridin-3-yl 1H-indole-2-carboxylate [no description available]	2.31	1	0	indolyl carboxylic acid	anticoronaviral agent
cellulose DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.	4.96	2	1	glycoside
quercetin [no description available]	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)	2.05	1	0
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	3.09	5	0	1,2-diacyl-sn-glycero-3-phosphocholine
atractyloside Atractyloside: A glycoside of a kaurene type diterpene that is found in some plants including Atractylis gummifera (ATRACTYLIS); COFFEE; XANTHIUM, and CALLILEPIS. Toxicity is due to inhibition of ADENINE NUCLEOTIDE TRANSLOCASE.	2.58	2	0
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.	8.53	8	0	chlorophyll; methyl ester	cofactor
phenylmercuric acetate Phenylmercuric Acetate: A phenyl mercury compound used mainly as a fungicide. Has also been used as a herbicide, slimicide, and bacteriocide.	2.31	1	0	arylmercury compound; benzenes
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.	2.31	1	0	alkylmercury compound	antifungal drug; antiseptic drug; disinfectant; drug allergen
sphingosine kinase [no description available]	2.58	2	0
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.	2.31	1	0
pinoresinol pinoresinol: in plants; a furo[3,4-c]furan created from dimer of coniferyl alcohol. pinoresinol : A lignan that is tetrahydro-1H,3H-furo[3,4-c]furan substituted at positions 1 and 4 by 4-hydroxy-3-methoxyphenyl groups.	8.51	7	0
dihydrorobinetin dihydrorobinetin: structure in first source	2.07	1	0
benzoylaconine benzoylaconine: alkaloid isolated from Aconitum carmichaeli. benzoylaconine : A diterpene alkaloid with formula C32H45NO10 that is isolated from several Aconitum species.	2.08	1	0	benzoate ester; bridged compound; diterpene alkaloid; organic heteropolycyclic compound; polyether; secondary alcohol; tertiary alcohol; tertiary amino compound; tetrol	phytotoxin; plant metabolite
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.	7.13	1	0
2-hydroxyursolic acid 2-hydroxyursolic acid: isolated from the stem bark of Physocarpus intermedius; structure in first source	2.08	1	0
hydroxyoctadecadienoic acid hydroxyoctadecadienoic acid: structure in first source	2.04	1	0
5,6,2',3',5',6'-hexamethoxyflavone 5,6,2',3',5',6'-hexamethoxyflavone: from the Yucatec Mayan plant Casimiroa tetrameria; structure in first source	2.1	1	0
ginsenoside rg2 ginsenoside Rg2: structure in first source; RN given refers to (6-deoxy-alpha-L-mannopyranosyl)-isomer. ginsenoside Rg2 : A ginsenoside found in Panax species that is dammarane which is substituted by hydroxy groups at the 3beta, 6alpha, 12beta and 20 pro-S positions, in which the hydroxy group at position 6 has been converted to the corresponding alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside, and in which a double bond has been introduced at the 24-25 position.	2.1	1	0	12beta-hydroxy steroid; 20-hydroxy steroid; 3beta-hydroxy-4,4-dimethylsteroid; 3beta-hydroxy steroid; beta-D-glucoside; disaccharide derivative; ginsenoside; tetracyclic triterpenoid	anticoagulant; cardioprotective agent; plant metabolite
notoginsenoside r2 notoginsenoside R2: from the roots of commercial ginseng	2.1	1	0	triterpenoid saponin
dipsacoside b dipsacoside B: from flowers of Lonicera macranthoides Hand	2.78	3	0
ilexgenin a ilexgenin A: extract from the leaves of the plant	2.08	1	0
chitosan [no description available]	4.44	17	0
9-(tetrahydro-2-furyl)-adenine [no description available]	2.1	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.	2.47	2	0	inorganic sodium salt; sulfite salt	allergen; food antioxidant; food colour retention agent; mutagen; reducing agent
sodium lactate Sodium Lactate: The sodium salt of racemic or inactive lactic acid. It is a hygroscopic agent used intravenously as a systemic and urinary alkalizer.. sodium lactate : An organic sodium salt having lactate as the counterion.	2.05	1	0	lactate salt; organic sodium salt	food acidity regulator; food preservative
monensin [no description available]	2.07	1	0
sodium nitrite Sodium Nitrite: Nitrous acid sodium salt. Used in many industrial processes, in meat curing, coloring, and preserving, and as a reagent in ANALYTICAL CHEMISTRY TECHNIQUES. It is used therapeutically as an antidote in cyanide poisoning. The compound is toxic and mutagenic and will react in vivo with secondary or tertiary amines thereby producing highly carcinogenic nitrosamines.. sodium nitrite : An inorganic sodium salt having nitrite as the counterion. Used as a food preservative and antidote to cyanide poisoning.	2.06	1	0	inorganic sodium salt; nitrite salt	antidote to cyanide poisoning; antihypertensive agent; antimicrobial food preservative; food antioxidant; poison
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.	2.61	2	0	monosodium glutamate	flavouring agent
angoroside c angoroside C: angoroside C is the (E)-isomer; structure in first source	2.41	1	0
forsythoside b forsythoside B: structure in first source	2.63	2	0
methyl jasmonate [no description available]	3.16	5	0
liriodendrin liriodendrin: 573-33-4 is liriodendrin; from bark of Plumeria rubra; structure given in first source	7.03	1	0
benzoylmesaconine benzoylmesaconine: structure in first source. benzoylmesaconine : A diterpene alkaloid with formula C31H43NO10 that is isolated from several Aconitum species.	2.08	1	0	benzoate ester; bridged compound; diterpene alkaloid; organic heteropolycyclic compound; polyether; secondary alcohol; tertiary alcohol; tertiary amino compound; tetrol	analgesic; antiinfective agent; plant metabolite
arabinogalactan [no description available]	2.11	1	0
catechin [no description available]	2.05	1	0
niraparib niraparib: structure in first source. niraparib : A 2-[4-(piperidin-3-yl)phenyl]-2H-indazole-7-carboxamide that has S-configuration. It is a potent inhibitor of PARP1 and PARP2 (IC50 of 3.8 and 2.1 nM, respectively) and approved as a first-line maintenance treatment for women with advanced ovarian cancer after responding to platinum-based chemotherapy.	4.8	1	1	2-[4-(piperidin-3-yl)phenyl]-2H-indazole-7-carboxamide	antineoplastic agent; apoptosis inducer; EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor; radiosensitizing agent
pc190723 PC190723: Antibacterial; an inhibitor of FtsZ with potent and selective anti-staphylococcal activity including methicillin- and multi-drug-resistant Staphylococcus aureus; structure in first source	3.23	1	0
egg white Egg White: The white of an egg, especially a chicken's egg, used in cooking. It contains albumin. (Random House Unabridged Dictionary, 2d ed)	2.17	1	0
cardiovascular agents Cardiovascular Agents: Agents that affect the rate or intensity of cardiac contraction, blood vessel diameter, or blood volume.	3.19	1	0
(5-Chloropyridin-3-yl) 1H-indole-4-carboxylate [no description available]	2.31	1	0	indolyl carboxylic acid	anticoronaviral agent
mannans [no description available]	2.07	1	0
plx4032 [no description available]	4.8	1	1	aromatic ketone; difluorobenzene; monochlorobenzenes; pyrrolopyridine; sulfonamide	antineoplastic agent; B-Raf inhibitor
glycolipids [no description available]	2.41	1	0
piperidines Piperidines: A family of hexahydropyridines.	5.79	6	1
resolvin d1 resolvin D1: an anti-inflammatory lipid mediator; structure in first source. resolvin D1 : A resolvin that is docosa-4Z,9E,11E,13Z,15E,19Z-hexaenoic acid which is substituted by hydroxy groups at the 7, 8, and 17 positions (the 7S,8R,17S-stereoisomer).	7.41	1	0	hydroxy polyunsaturated fatty acid; resolvin; triol	anti-inflammatory agent
cyanidin 3-galactoside cyanidin 3-galactoside: structure in first source	2.53	2	0
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.	3.63	8	0
typhaneoside typhaneoside: isolated from pollen of Typha angustfolia L. (puhuang); structure given in first source	2.21	1	0	flavonoids; glycoside
phillyrin [no description available]	3.14	5	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.	2.1	1	0	12beta-hydroxy steroid; beta-D-glucoside; disaccharide derivative; ginsenoside; tetracyclic triterpenoid	plant metabolite
Benzyl N-[(2S)-3-methyl-1-[[(2S)-4-methyl-1-oxo-1-[[(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]-1-(1,3-thiazol-2-yl)propan-2-yl]amino]pentan-2-yl]amino]-1-oxobutan-2-yl]carbamate [no description available]	2.31	1	0	dipeptide	anticoronaviral agent
amg-837 AMG-837: GPR40 agonist	2.31	1	0
chrysophaentin a chrysophaentin A: structure in first source	3.23	1	0
(20R)-ginsenoside Rg3 (20R)-ginsenoside Rg3 : A ginsenoside found in Panax japonicus var. major that is dammarane which is substituted by hydroxy groups at the 3beta, 12beta and 20 pro-R 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.	2.1	1	0	ginsenoside; glycoside; tetracyclic triterpenoid	antioxidant; plant metabolite
N-[(1R)-2-(tert-butylamino)-2-oxo-1-(3-pyridinyl)ethyl]-N-(4-tert-butylphenyl)-2-furancarboxamide [no description available]	2.31	1	0	aromatic amide; furans
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.	1.95	1	0
isoquercitrin [no description available]	9.43	20	0
gardenoside gardenoside: structure given in first source; RN given refers to 1S(1alpha,4alpha,7alpha,7aalpha)-isomer. gardenoside : A cyclopentapyran that is 7-deoxyloganin with a methyl and hydrogen replaced by hydroxy and hydroxymethyl groups at position 7.	2.1	1	0	beta-D-glucoside; cyclopentapyran; enoate ester; methyl ester; monosaccharide derivative; tertiary alcohol	metabolite
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.	1.96	1	0
heparitin sulfate Heparitin Sulfate: A heteropolysaccharide that is similar in structure to HEPARIN. It accumulates in individuals with MUCOPOLYSACCHARIDOSIS.	2.41	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.	5.49	63	0	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.	3.1	1	0
minocycline Minocycline: A TETRACYCLINE analog, having a 7-dimethylamino and lacking the 5 methyl and hydroxyl groups, which is effective against tetracycline-resistant STAPHYLOCOCCUS infections.. minocycline : A tetracycline analogue having a dimethylamino group at position 7 and lacking the methyl and hydroxy groups at position 5.	2.07	1	0
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.	3.08	5	0	monohydroxybenzoate	plant metabolite
dicumarol Dicumarol: An oral anticoagulant that interferes with the metabolism of vitamin K. It is also used in biochemical experiments as an inhibitor of reductases.	2.07	1	0	hydroxycoumarin	anticoagulant; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; Hsp90 inhibitor; vitamin K antagonist
piroxicam [no description available]	2.42	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.	6.35	30	0	benzenes; hydroxycoumarin; methyl ketone
citrinin Citrinin: Antibiotic and mycotoxin from Aspergillus niveus and Penicillium citrinum.	2.07	1	0
4-hydroxycoumarin 2-hydroxychromone: structure	3.1	1	0	hydroxycoumarin
vulpinic acid vulpinic acid: RN given refers to cpd without isomeric designation; structure given in first source; vulpinic acid refers to (E)-isomer	2.07	1	0	butenolide
byl719 [no description available]	4.8	1	1	proline derivative
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.	2.17	1	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.	2.08	1	0
phytoestrogens Phytoestrogens: Compounds derived from plants, primarily ISOFLAVONES that mimic or modulate endogenous estrogens, usually by binding to ESTROGEN RECEPTORS.	2.03	1	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.	2.05	1	0	ketal
pyrethrins [no description available]	2.45	2	0
ajmaline [no description available]	2.07	1	0
maysin maysin: structure in first source. maysin : A flavone C-glycoside that is luteolin attached to a disaccharide residue at position 6. It has been isolated from natural product Petrorhagia velutina and Zea mays and exhibits insecticidal and neuroprotective activities.	2.72	3	0	disaccharide derivative; flavone C-glycoside; secondary alpha-hydroxy ketone; tetrahydroxyflavone	insecticide; neuroprotective agent; plant metabolite
macranthoidin b [no description available]	2.78	3	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.	2.38	2	0
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.	3.03	4	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.	3.14	5	0
kudinoside a kudinoside A: isolated from leaves of Ilex kudincha; structure in first source	2.17	1	0
thearubigin thearubigin: from black tea leaves; a catechin oxidized product; a mixture of heterogenous polyphenols	6.99	1	0
cyanidin 3-sambubioside cyanidin 3-sambubioside: structure in first source	2.07	1	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.	2.06	1	0
nitrophenols Nitrophenols: PHENOLS carrying nitro group substituents.	1.94	1	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.	2.9	2	0	cyclodepsipeptide; cyclooctadepsipeptide	antineoplastic agent; fungal metabolite; insecticide
bictegravir bictegravir: HIV Integrase Inhibitors. bictegravir : A monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2R,5S,13aR)-8-hydroxy-7,9-dioxo-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxylic acid with the amino group of 2,4,6-trifluorobenzylamine. It is a second-generation integrase strand transfer inhibitor (INSTI) and used (as its sodium salt) for the treatment of HIV-1.	2.31	1	0	monocarboxylic acid amide; organic heterotetracyclic compound; secondary carboxamide; trifluorobenzene	HIV-1 integrase inhibitor
isookanin isookanin: from Bidens bipinnata; structure in first source	2.13	1	0
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.	2.72	3	0
punicalin punicalin: hepatoprotective agent isolated from Terminalia catappa	2.25	1	0	tannin
5,6-epoxyretinoic acid 5,6-epoxyretinoic acid: RN given refers to parent cpd without isomeric designation. 5,6-epoxyretinoic acid : A retinoid obtained by epoxidation across the 5,6-double bond of retinoic acid.	1.96	1	0
rabdosiin rabdosiin: isolated from the stem of Rabdosia Japonica; structure in first source	1.99	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.	2.52	2	0
carboxyatractyloside carboxyatractyloside: RN given refers to parent cpd; structure	2.21	1	0
tridihexethyl mesaconitine: RN given refers to parent cpd(1alpha,3alpha,6alpha,14alpha,15alpha,16beta)-isomer	2.6	1	0
t-2 toxin T-2 Toxin: A potent mycotoxin produced in feedstuffs by several species of the genus FUSARIUM. It elicits a severe inflammatory reaction in animals and has teratogenic effects.. T-2 toxin : A trichothecene mycotoxin produced by fungi of the genus Fusarium. It is a common contaminant in food and feedstuffs of cereal origin and is known to cause a range of toxic effects in humans and animals.	2.13	1	0
ht-2 toxin HT-2 toxin : A trichothecene mycotoxin that is T-2 toxin in which the acetyloxy group at position 4S has been hydrolysed to the corresponding hydroxy group. It is the major metabolite of T-2 toxin.	2.13	1	0
baccharin baccharin: antileukemic trichothecene triepoxide isolated from Baccharis megapotamica, a higher plant but may be plant-altered fungal metabolite; structure	2.05	1	0
peoniflorin peoniflorin: from Radix and of Paeonia suffruticosa	2.49	2	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.	3.81	2	1
aconitine Aconitine: A C19 norditerpenoid alkaloid (DITERPENES) from the root of ACONITUM; DELPHINIUM and larkspurs. It activates VOLTAGE-GATED SODIUM CHANNELS. It has been used to induce ARRHYTHMIAS in experimental animals and it has anti-inflammatory and anti-neuralgic properties.. aconitine : A diterpenoid that is 20-ethyl-3alpha,13,15alpha-trihydroxy-1alpha,6alpha,16beta-trimethoxy-4-(methoxymethyl)aconitane-8,14alpha-diol having acetate and benzoate groups at the 8- and 14-positions respectively.	2.08	1	0
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).	2.63	2	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.	2.13	1	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.	7.83	3	0
akebia saponin d akebia saponin D: isolated from Dipsacus asper; structure in first source. akebia saponin D : A triterpenoid saponin that is hederagenin attached to a alpha-L-arabinopyranosyl residue at position 3 via a glycosidic linkage and a 6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl residue at position 28 via an ester linkage. It is the active ingredient found in the traditional Chinese herb Radix Dipsaci.	2.15	1	0
neohesperidin [no description available]	2.08	1	0
alpha-solanine [no description available]	2.05	1	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.	3.27	6	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	2.05	1	0
senkyunolide i senkyunolide I: has antioxidant and anti-migraine activities; isolated from Ligusticum chuanxiong; structure in first source	2.25	1	0
liriodendrin, 1r-(1alpha,3abeta,4beta,6aalpha)-isomer eleutheroside E: from Eleutherococcus senticosus extract	2.07	1	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)	2.49	2	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.	2.06	1	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.	2.54	2	0	3',5'-cyclic purine nucleotide; guanyl ribonucleotide	Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
deoxyguanosine [no description available]	7.71	3	0	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
dihydrofolate dihydrofolic acid : A folic acid derivative acted upon by dihydrofolate reductase to produce tetrahydrofolic acid. It interacts with bacteria during cell division and is targeted by various drugs to prevent nucleic acid synthesis.	2	1	0	dihydrofolic acids	Escherichia coli metabolite; mouse metabolite
guanine [no description available]	2.06	1	0	2-aminopurines; oxopurine; purine nucleobase	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
hypoxanthine [no description available]	2.31	1	0	nucleobase analogue; oxopurine; purine nucleobase	fundamental 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.	4.16	3	1	folic acids; N-acyl-amino acid	human metabolite; mouse metabolite; nutrient
viomycin [no description available]	2	1	0	heterodetic cyclic peptide; peptide antibiotic	antitubercular agent
pheophytin a pheophytin a: structure given in first source; RN given refers to (3S-(3alpha(2E,7S,11S),4beta,21beta))-isomer	2.98	4	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)	3.53	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.	3.1	1	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
dacarbazine (E)-dacarbazine : A dacarbazine in which the N=N double bond adopts a trans-configuration.	3.99	1	1	dacarbazine
sildenafil sildenafil : A pyrazolo[4,3-d]pyrimidin-7-one having a methyl substituent at the 1-position, a propyl substituent at the 3-position and a 2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl group at the 5-position.	2.31	1	0	piperazines; pyrazolopyrimidine; sulfonamide	EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor; vasodilator agent
penciclovir penciclovir : A member of the class of 2-aminopurines that is guanine in which the hydrogen at position 9 is substituted by a 4-hydroxy-3-(hydroxymethyl)but-1-yl group. An antiviral drug, it is administered topically for treatment of herpes labialis. A prodrug, famciclovir, is used for oral administration.	2.06	1	0	2-aminopurines; propane-1,3-diols	antiviral drug
salinazid [no description available]	2.1	1	0	aromatic carboxylic acid; pyridinemonocarboxylic acid
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.	4.03	13	0	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger
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.	3.1	1	0	dibenzodiazepine; organochlorine compound; piperazines	delta-opioid receptor agonist; metabolite; serotonergic antagonist
phthivazide [no description available]	2.1	1	0
oosporein oosporein: from Chaetomium trilaterale; found in moldy peanuts	7.21	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	1.96	1	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.	2.71	3	0	guanosines	biomarker
amg531 [no description available]	2.31	1	0
alpha-cyclopiazonic acid [no description available]	2.07	1	0	alpha-cyclopiazonic acids
fagopyrin [no description available]	2.02	1	0
lipoteichoic acid lipoteichoic acid: lipopolysaccharides with an acyl group anchored to the cell membrane of gram-positive bacteria; functions as an adhesion molecule to facilitate the binding of bacteria to cells, colonization, and invasion; interacts with CD14 to induce NF-κB activation and inflammatory cytokine production; can function as surface antigen; inhibits remineraliztion of artificial lesions and surface-softened enamels;. lipoteichoic acid : A teichoic acid which is covalently bound to a lipid.	2.6	1	0
fructooligosaccharide [no description available]	2.59	2	0	oligosaccharide
maltodextrin maltodextrin : A dextrin in which the D-glucose units are linked by alpha-(1->4) glycosidic bonds.	8.14	4	0
N-[(2S)-3-cyclohexyl-1-oxo-1-({(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}amino)propan-2-yl]-1H-indole-2-carboxamide N-[(2S)-3-cyclohexyl-1-oxo-1-({(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}amino)propan-2-yl]-1H-indole-2-carboxamide : A secondary carboxamide resulting from the formal condensation of the carboxy group of 1H-indole-2-carboxylic acid with the primary amino group of 3-cyclohexyl-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-alaninamide. It is an inhibitor of SARS coronavirus main proteinase and inhibits SARS-CoV-2 replication in cell culture (EC50 = 0.53 muM).	2.31	1	0	aldehyde; indolecarboxamide; oligopeptide; pyrrolidin-2-ones; secondary carboxamide	anticoronaviral agent; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor
enhydrin enhydrin: from Tetragonotheca sp. (Asteraceae); structure in first source	2.49	2	0	sesquiterpene lactone
3-fluoro-Nalpha-(1H-indol-2-ylcarbonyl)-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide 3-fluoro-Nalpha-(1H-indol-2-ylcarbonyl)-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide : A secondary carboxamide resulting from the formal condensation of the carboxy group of 1H-indole-2-carboxylic acid with the primary amino group of 3-fluoro-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide. It is an inhibitor of SARS coronavirus main proteinase and inhibits SARS-CoV-2 replication in cell culture (EC50 = 0.72 muM).	2.31	1	0	aldehyde; indolecarboxamide; monofluorobenzenes; oligopeptide; pyrrolidin-2-ones; secondary carboxamide	anticoronaviral agent; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor
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.	7.15	1	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.	3.01	4	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.	5.74	5	1
pyrimidinones Pyrimidinones: Heterocyclic compounds known as 2-pyrimidones (or 2-hydroxypyrimidines) and 4-pyrimidones (or 4-hydroxypyrimidines) with the general formula C4H4N2O.	2.93	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.	2.82	3	0

Condition	Indicated	Relationship Strength	Studies	Trials
Bilirubinemia [description not available]	0	2.92	1	0
Benign Neoplasms [description not available]	0	9.52	24	2
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.	1	11.52	24	2
Cancer of Colon [description not available]	0	4.31	18	0
Colonic Neoplasms Tumors or cancer of the COLON.	0	4.31	18	0
Liver Dysfunction [description not available]	0	6.5	9	1
Liver Diseases Pathological processes of the LIVER.	0	6.5	9	1
Innate Inflammatory Response [description not available]	0	12.83	95	6
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.	0	12.83	95	6
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	0	15.85	44	4
Bleeding [description not available]	0	4.84	2	1
Hemorrhage Bleeding or escape of blood from a vessel.	0	4.84	2	1
Encephalitis, Polio [description not available]	0	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)	0	2.06	1	0
Acute Confusional Senile Dementia [description not available]	0	4.03	12	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)	0	4.03	12	0
Diabetes Mellitus, Adult-Onset [description not available]	0	14.24	55	4
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.	0	14.24	55	4
Amyloid Neuropathy Type 1 [description not available]	0	2.1	1	0
Amyloidosis A group of sporadic, familial and/or inherited, degenerative, and infectious disease processes, linked by the common theme of abnormal protein folding and deposition of AMYLOID. As the amyloid deposits enlarge they displace normal tissue structures, causing disruption of function. Various signs and symptoms depend on the location and size of the deposits.	0	2.1	1	0
Amyloid Neuropathies, Familial Inherited disorders of the peripheral nervous system associated with the deposition of AMYLOID in nerve tissue. The different clinical types based on symptoms correspond to the presence of a variety of mutations in several different proteins including transthyretin (PREALBUMIN); APOLIPOPROTEIN A-I; and GELSOLIN.	0	2.1	1	0
Glial Cell Tumors [description not available]	0	6.35	6	2
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)	0	6.35	6	2
Anemia, Fanconi [description not available]	0	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)	0	2.13	1	0
Degenerative Diseases, Central Nervous System [description not available]	0	6.16	12	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.	0	6.16	12	0
Bacterial Disease [description not available]	0	3.09	1	0
Bacterial Infections Infections by bacteria, general or unspecified.	0	3.09	1	0
Experimental Neoplasms [description not available]	0	3.6	2	0
Acquired Immune Deficiency Syndrome [description not available]	0	2.75	3	0
HIV Coinfection [description not available]	0	2.76	2	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.	0	2.75	3	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).	0	2.76	2	0
Malignant Melanoma [description not available]	0	6.12	5	1
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)	0	11.12	5	1
Acute Ischemic Stroke [description not available]	0	4.45	3	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.	0	4.45	3	1
Arthritis, Degenerative [description not available]	0	5.7	6	1
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.	0	5.7	6	1
Cancer of Stomach [description not available]	0	10.09	12	9
Stomach Neoplasms Tumors or cancer of the STOMACH.	0	10.09	12	9
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	0	12.89	118	10
Experimental Lung Inflammation Inflammation of any part, segment or lobe, of the lung parenchyma.	0	3.36	5	0
Pneumonia Infection of the lung often accompanied by inflammation.	0	3.36	5	0
Alloxan Diabetes [description not available]	0	7.19	31	1
Hyperglycemia, Postprandial Abnormally high BLOOD GLUCOSE level after a meal.	0	6.03	9	0
Hyperglycemia Abnormally high BLOOD GLUCOSE level.	0	11.03	9	0
Diabetic Cardiomyopathies Diabetes complications in which VENTRICULAR REMODELING in the absence of CORONARY ATHEROSCLEROSIS and hypertension results in cardiac dysfunctions, typically LEFT VENTRICULAR DYSFUNCTION. The changes also result in myocardial hypertrophy, myocardial necrosis and fibrosis, and collagen deposition due to impaired glucose tolerance.	0	2.76	2	0
Anoxemia [description not available]	0	3.43	6	0
Hypoxia Sub-optimal OXYGEN levels in the ambient air of living organisms.	0	3.43	6	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.	0	2.72	2	0
Idiopathic Parkinson Disease [description not available]	0	9.66	16	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)	0	9.66	16	0
Atrophy, Muscle [description not available]	0	2.31	1	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.	0	2.31	1	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.	0	6.29	6	2
Weight Gain Increase in BODY WEIGHT over existing weight.	0	4.75	10	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.	0	7.55	2	0
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.	0	6.29	6	2
Cardiac Failure [description not available]	0	8.07	6	4
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.	0	8.07	6	4
Injuries, Spinal Cord [description not available]	0	2.66	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.).	0	2.66	2	0
Cerebral Infarction, Middle Cerebral Artery [description not available]	0	6.62	8	2
Cerebral Ischemia [description not available]	0	7.08	14	2
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.	0	7.08	14	2
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.	0	6.62	8	2
Disbacteriosis [description not available]	0	3.65	7	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).	0	9.51	37	2
Diabetic Retinopathy Disease of the RETINA as a complication of DIABETES MELLITUS. It is characterized by the progressive microvascular complications, such as ANEURYSM, interretinal EDEMA, and intraocular PATHOLOGIC NEOVASCULARIZATION.	0	3.07	4	0
Cognitive Decline [description not available]	0	6.83	11	1
Cognitive Dysfunction Diminished or impaired mental and/or intellectual function.	0	11.83	11	1
Injury, Ischemia-Reperfusion [description not available]	0	8.78	14	4
Reperfusion Injury Adverse functional, metabolic, or structural changes in tissues that result from the restoration of blood flow to the tissue (REPERFUSION) following ISCHEMIA.	0	8.78	14	4
Contact Dermatitis [description not available]	0	2.9	4	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.	0	2.9	4	0
Elevated Cholesterol [description not available]	0	6.22	7	1
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.	0	6.22	7	1
Spermatic Cord Torsion The twisting of the SPERMATIC CORD due to an anatomical abnormality that left the TESTIS mobile and dangling in the SCROTUM. The initial effect of testicular torsion is obstruction of venous return. Depending on the duration and degree of cord rotation, testicular symptoms range from EDEMA to interrupted arterial flow and testicular pain. If blood flow to testis is absent for 4 to 6 h, SPERMATOGENESIS may be permanently lost.	0	2.41	1	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.	0	5.72	5	1
Kidney Stones [description not available]	0	2.41	1	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.	0	2.41	1	0
Pericementitis [description not available]	0	5.53	4	1
Periodontitis Inflammation and loss of connective tissues supporting or surrounding the teeth. This may involve any part of the PERIODONTIUM. Periodontitis is currently classified by disease progression (CHRONIC PERIODONTITIS; AGGRESSIVE PERIODONTITIS) instead of age of onset. (From 1999 International Workshop for a Classification of Periodontal Diseases and Conditions, American Academy of Periodontology)	0	10.53	4	1
Enterovirus Infections Diseases caused by ENTEROVIRUS.	0	2.85	3	0
Fatty Liver, Nonalcoholic [description not available]	0	7.45	20	2
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)	0	2.41	1	0
Cirrhosis, Liver [description not available]	0	11.29	19	1
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.	0	11.29	19	1
Non-alcoholic Fatty Liver Disease Fatty liver finding without excessive ALCOHOL CONSUMPTION.	0	7.45	20	2
Age-Related Osteoporosis [description not available]	0	9.34	13	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.	0	14.34	13	0
Blood Pressure, High [description not available]	0	9.61	15	4
Cardiovascular Diseases Pathological conditions involving the CARDIOVASCULAR SYSTEM including the HEART; the BLOOD VESSELS; or the PERICARDIUM.	0	14.53	30	10
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.	0	9.61	15	4
Breast Cancer [description not available]	0	9.01	19	4
Breast Neoplasms Tumors or cancer of the human BREAST.	0	9.01	19	4
Allergy, Food [description not available]	0	6.08	11	0
Food Hypersensitivity Gastrointestinal disturbances, skin eruptions, or shock due to allergic reactions to allergens in food.	0	6.08	11	0
Liver Steatosis [description not available]	0	7.67	21	1
Alcoholic Fatty Liver [description not available]	0	7.63	2	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.	0	7.67	21	1
Insulin Sensitivity [description not available]	0	14.4	46	9
Prediabetes [description not available]	0	8.16	3	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.	0	14.4	46	9
Prediabetic State The time period before the development of symptomatic diabetes. For example, certain risk factors can be observed in subjects who subsequently develop INSULIN RESISTANCE as in type 2 diabetes (DIABETES MELLITUS, TYPE 2).	0	3.16	3	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.	0	9.25	16	4
Pain, Chronic [description not available]	0	3.79	3	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.	0	8.79	3	0
Anoxia-Ischemia, Brain [description not available]	0	2.41	1	0
Acute Brain Injuries [description not available]	0	5.37	3	1
Infarct [description not available]	0	2.41	1	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.	0	5.37	3	1
Hypoxia-Ischemia, Brain A disorder characterized by a reduction of oxygen in the blood combined with reduced blood flow (ISCHEMIA) to the brain from a localized obstruction of a cerebral artery or from systemic hypoperfusion. Prolonged hypoxia-ischemia is associated with ISCHEMIC ATTACK, TRANSIENT; BRAIN INFARCTION; BRAIN EDEMA; COMA; and other conditions.	0	7.41	1	0
Alcoholic Liver Diseases [description not available]	0	3.81	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.	0	3.81	2	0
Esophageal Squamous Cell Carcinoma A carcinoma that originates usually from cells on the surface of the middle and lower third of the ESOPHAGUS. Tumor cells exhibit typical squamous morphology and form large polypoid lesions. Mutations in RNF6, LZTS1, TGFBR2, DEC1, and WWOX1 genes are associated with this cancer.	0	5.31	3	1
Cancer of Esophagus [description not available]	0	5.31	3	1
Invasiveness, Neoplasm [description not available]	0	3.36	6	0
Esophageal Neoplasms Tumors or cancer of the ESOPHAGUS.	0	5.31	3	1
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.	0	3.47	6	0
Chondrodystrophic Myotonia [description not available]	0	3.21	4	0
Atherogenesis [description not available]	0	5.94	8	1
Atherosclerosis A thickening and loss of elasticity of the walls of ARTERIES that occurs with formation of ATHEROSCLEROTIC PLAQUES within the ARTERIAL INTIMA.	0	5.94	8	1
Multiple Primary Neoplasms [description not available]	0	2.41	1	0
Brain Hemorrhage, Cerebral [description not available]	0	2.41	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.	0	7.41	1	0
Hepatocellular Carcinoma [description not available]	0	11.48	25	1
Cancer of Liver [description not available]	0	11.94	31	1
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.	0	11.48	25	1
Liver Neoplasms Tumors or cancer of the LIVER.	0	11.94	31	1
Chronic Kidney Diseases [description not available]	0	2.41	1	0
Cirrhosis [description not available]	0	3.27	4	0
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	0	3.27	4	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.	0	3.7	8	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)	0	2.41	1	0
2019 Novel Coronavirus Disease [description not available]	0	8.09	6	4
Diabetes Mellitus A heterogeneous group of disorders characterized by HYPERGLYCEMIA and GLUCOSE INTOLERANCE.	0	14.63	16	5
Apoplexy [description not available]	0	4.95	7	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)	0	4.95	7	1
Mastitis, Bovine INFLAMMATION of the UDDER in cows.	0	3.18	4	0
Infections, Staphylococcal [description not available]	0	3.12	4	0
Staphylococcal Infections Infections with bacteria of the genus STAPHYLOCOCCUS.	0	3.12	4	0
Angiogenesis, Pathologic [description not available]	0	8.24	8	4
Ache [description not available]	0	3.58	8	0
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	0	3.58	8	0
Colitis Gravis [description not available]	0	4.07	5	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.	0	3.67	8	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.	0	4.07	5	0
Blood Clot [description not available]	0	5.44	7	0
Thrombosis Formation and development of a thrombus or blood clot in the blood vessel.	0	5.44	7	0
Adjuvant Arthritis [description not available]	0	2.86	3	0
Rheumatoid Arthritis [description not available]	0	2.94	3	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.	0	2.94	3	0
Chronic Lung Injury [description not available]	0	2.63	2	0
Acute Respiratory Distress Syndrome [description not available]	0	5.41	3	1
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.	0	5.41	3	1
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)	0	2.59	2	0
Retinal Diseases Diseases involving the RETINA.	0	2.81	3	0
Cancer of Ovary [description not available]	0	3.5	6	0
Acute Bacterial Prostatitis [description not available]	0	2.57	2	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.	0	3.5	6	0
Prostatitis Infiltration of inflammatory cells into the parenchyma of PROSTATE. The subtypes are classified by their varied laboratory analysis, clinical presentation and response to treatment.	0	2.57	2	0
Break-Bone Fever [description not available]	0	2.41	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.	0	2.41	1	0
Carcinoma, Epidermoid [description not available]	0	6.39	11	1
Cancer of Skin [description not available]	0	4.99	13	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)	0	6.39	11	1
Skin Neoplasms Tumors or cancer of the SKIN.	0	4.99	13	0
Colorectal Cancer [description not available]	0	10.21	23	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.	0	10.21	23	0
Acne [description not available]	0	2.82	2	0
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.	0	7.82	2	0
Gastric Ulcer [description not available]	0	3.67	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).	0	3.67	9	0
Ulcer A lesion on the surface of the skin or a mucous surface, produced by the sloughing of inflammatory necrotic tissue.	0	7.6	1	0
Idiopathic Inflammatory Myopathies [description not available]	0	2.6	1	0
Myositis Inflammation of a muscle or muscle tissue.	0	2.6	1	0
E coli Infections [description not available]	0	2.6	1	0
Escherichia coli Infections Infections with bacteria of the species ESCHERICHIA COLI.	0	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.	0	11.6	6	1
Acute Liver Injury, Drug-Induced [description not available]	0	7.02	26	1
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.	0	3.01	2	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.	0	2.69	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.	0	7.02	26	1
Lung Injury, Acute [description not available]	0	3.25	5	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).	0	3.25	5	0
Mastitis INFLAMMATION of the BREAST, or MAMMARY GLAND.	0	7.59	2	0
Minimal Disease, Residual [description not available]	0	2.6	1	0
Bone Cancer [description not available]	0	3.01	3	0
Osteogenic Sarcoma [description not available]	0	3.21	4	0
Bone Neoplasms Tumors or cancer located in bone tissue or specific BONES.	0	3.01	3	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)	0	3.21	4	0
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	0	5.93	7	1
Cryptosporidium Infection [description not available]	0	2.6	1	0
Cryptosporidiosis Intestinal infection with organisms of the genus CRYPTOSPORIDIUM. It occurs in both animals and humans. Symptoms include severe DIARRHEA.	0	7.6	1	0
Benign Neoplasms, Brain [description not available]	0	8.31	6	5
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.	0	8.31	6	5
Alveolitis, Fibrosing [description not available]	0	2.66	2	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.	0	2.66	2	0
Polycystic Ovarian Syndrome [description not available]	0	8.52	1	0
Polycystic Ovary Syndrome A complex disorder characterized by infertility, HIRSUTISM; OBESITY; and various menstrual disturbances such as OLIGOMENORRHEA; AMENORRHEA; ANOVULATION. Polycystic ovary syndrome is usually associated with bilateral enlarged ovaries studded with atretic follicles, not with cysts. The term, polycystic ovary, is misleading.	0	3.52	1	0
Depression Depressive states usually of moderate intensity in contrast with MAJOR DEPRESSIVE DISORDER present in neurotic and psychotic disorders.	0	3.02	4	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.	0	8.51	7	0
Colitis, Mucous [description not available]	0	2.6	1	0
Irritable Bowel Syndrome A disorder with chronic or recurrent colonic symptoms without a clearcut etiology. This condition is characterized by chronic or recurrent ABDOMINAL PAIN, bloating, MUCUS in FECES, and an erratic disturbance of DEFECATION.	0	7.6	1	0
Weight Reduction [description not available]	0	7.29	7	2
Weight Loss Decrease in existing BODY WEIGHT.	0	7.29	7	2
Injury, Myocardial Reperfusion [description not available]	0	2.63	2	0
Intestinal Diseases Pathological processes in any segment of the INTESTINE from DUODENUM to RECTUM.	0	2.21	1	0
Age-Related Memory Disorders [description not available]	0	4.3	6	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.	0	4.3	6	0
Bowel Diseases, Inflammatory [description not available]	0	2.51	2	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.	0	2.51	2	0
ER-Negative PR-Negative HER2-Negative Breast Cancer [description not available]	0	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.	0	2.9	3	0
Bacteroidaceae Infections Infections with bacteria of the family BACTEROIDACEAE.	0	2.21	1	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)	0	6.52	42	1
Adenocarcinoma Of Kidney [description not available]	0	2.21	1	0
Cancer of Kidney [description not available]	0	2.21	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.	0	2.21	1	0
Kidney Neoplasms Tumors or cancers of the KIDNEY.	0	2.21	1	0
Tetraploid [description not available]	0	2.58	2	0
Blood Poisoning [description not available]	0	3.73	3	0
Brain Inflammation [description not available]	0	3.17	1	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.	0	3.17	1	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.	0	8.73	3	0
Gouty Arthritis [description not available]	0	2.59	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.	0	2.59	2	0
Cancer of Pancreas [description not available]	0	2.63	2	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).	0	2.63	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)	0	7.25	1	0
Bladder Pain Syndrome [description not available]	0	2.25	1	0
Cystitis, Interstitial A condition with recurring discomfort or pain in the URINARY BLADDER and the surrounding pelvic region without an identifiable disease. Severity of pain in interstitial cystitis varies greatly and often is accompanied by increased urination frequency and urgency.	0	2.25	1	0
Candida Infection [description not available]	0	2.5	2	0
Dermatomycoses Superficial infections of the skin or its appendages by any of various fungi.	0	2.25	1	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)	0	2.5	2	0
Dermatoses [description not available]	0	3.64	1	1
Skin Diseases Diseases involving the DERMIS or EPIDERMIS.	0	3.64	1	1
Anasarca [description not available]	0	4.25	17	0
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	0	4.25	17	0
Ureteral Obstruction Blockage in any part of the URETER causing obstruction of urine flow from the kidney to the URINARY BLADDER. The obstruction may be congenital, acquired, unilateral, bilateral, complete, partial, acute, or chronic. Depending on the degree and duration of the obstruction, clinical features vary greatly such as HYDRONEPHROSIS and obstructive nephropathy.	0	2.25	1	0
Complications of Diabetes Mellitus [description not available]	0	8.73	12	4
Bacteroides Infections Infections with bacteria of the genus BACTEROIDES.	0	2.25	1	0
Allergy, Peanut [description not available]	0	2.25	1	0
Peanut Hypersensitivity Allergic reaction to peanuts that is triggered by the immune system.	0	2.25	1	0
Dyslipidemia [description not available]	0	4.38	2	0
Abdominal Obesity [description not available]	0	3.17	1	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.	0	4.38	2	0
Infections, Coronavirus [description not available]	0	5.29	3	1
Pneumonia, Viral Inflammation of the lung parenchyma that is caused by a viral infection.	0	4.99	2	1
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).	0	5.29	3	1
Disease Exacerbation [description not available]	0	7.91	5	4
Genetic Predisposition [description not available]	0	4.83	2	1
Chronic Illness [description not available]	0	5.79	4	1
Attachment Loss, Periodontal [description not available]	0	4.62	1	1
Chemical Dependence [description not available]	0	4.77	2	1
Osteoarthritis of Knee [description not available]	0	4.62	1	1
Deafness, Transitory [description not available]	0	4.62	1	1
Liver Abscess, Pyogenic Single or multiple areas of PUS due to bacterial infection within the hepatic parenchyma. It can be caused by a variety of BACTERIA, local or disseminated from infections elsewhere such as in APPENDICITIS; CHOLECYSTITIS; PERITONITIS; and after LIVER TRANSPLANTATION.	0	4.62	1	1
Acute Kidney Failure [description not available]	0	8.09	7	4
Adverse Drug Event [description not available]	0	4.82	2	1
Ancylostomiasis Infection of humans or animals with hookworms of the genus ANCYLOSTOMA. Characteristics include anemia, dyspepsia, eosinophilia, and abdominal swelling.	0	4.62	1	1
Auricular Fibrillation [description not available]	0	4.62	1	1
Bladder Cancer [description not available]	0	4.62	1	1
Bladder Disorder, Neurogenic [description not available]	0	4.62	1	1
Carcinoma, Non-Small Cell Lung [description not available]	0	5.61	5	1
Caries, Dental [description not available]	0	4.62	1	1
Canine Diseases [description not available]	0	4.62	1	1
Fistula Abnormal communication most commonly seen between two internal organs, or between an internal organ and the surface of the body.	0	4.62	1	1
Cancer of Gastrointestinal Tract [description not available]	0	5.43	2	1
Astrocytoma, Grade IV [description not available]	0	4.92	2	1
Focal Segmental Glomerulosclerosis [description not available]	0	4.62	1	1
Infections, Klebsiella [description not available]	0	4.99	2	1
Cancer of Lung [description not available]	0	6.41	14	1
Mitral Incompetence [description not available]	0	4.62	1	1
Kahler Disease [description not available]	0	4.62	1	1
Cardiomyopathies, Primary [description not available]	0	4.62	1	1
Morbid Obesity [description not available]	0	4.62	1	1
Pocket, Periodontal [description not available]	0	4.62	1	1
Complication, Postoperative [description not available]	0	4.62	1	1
Condition, Preneoplastic [description not available]	0	5.27	4	1
Cancer of Prostate [description not available]	0	7.74	4	4
Embolism, Pulmonary [description not available]	0	4.62	1	1
Sarcoma, Epithelioid [description not available]	0	4.85	2	1
Linear Skull Fracture [description not available]	0	4.62	1	1
Nicotine Addiction [description not available]	0	4.62	1	1
Zoonoses Diseases of non-human animals that may be transmitted to HUMANS or may be transmitted from humans to non-human animals.	0	4.62	1	1
Coxarthrosis [description not available]	0	4.62	1	1
MPTP Neurotoxicity Syndrome [description not available]	0	4.62	1	1
Shoulder Injuries Injuries involving the SHOULDERS and SHOULDER JOINT.	0	4.62	1	1
Hemorrhage, Gingival [description not available]	0	4.62	1	1
Local Neoplasm Recurrence [description not available]	0	4.62	1	1
Acute Disease Disease having a short and relatively severe course.	0	4.8	2	1
Atrial Fibrillation Abnormal cardiac rhythm that is characterized by rapid, uncoordinated firing of electrical impulses in the upper chambers of the heart (HEART ATRIA). In such case, blood cannot be effectively pumped into the lower chambers of the heart (HEART VENTRICLES). It is caused by abnormal impulse generation.	0	4.62	1	1
Biliary Tract Diseases Diseases in any part of the BILIARY TRACT including the BILE DUCTS and the GALLBLADDER.	0	4.62	1	1
Urinary Bladder Neoplasms Tumors or cancer of the URINARY BLADDER.	0	4.62	1	1
Urinary Bladder, Neurogenic Dysfunction of the URINARY BLADDER due to disease of the central or peripheral nervous system pathways involved in the control of URINATION. This is often associated with SPINAL CORD DISEASES, but may also be caused by BRAIN DISEASES or PERIPHERAL NERVE DISEASES.	0	4.62	1	1
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.	0	5.61	5	1
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).	0	5.79	4	1
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.	0	4.62	1	1
Gingival Hemorrhage The flowing of blood from the marginal gingival area, particularly the sulcus, seen in such conditions as GINGIVITIS, marginal PERIODONTITIS, injury, and ASCORBIC ACID DEFICIENCY.	0	4.62	1	1
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.	1	11.92	2	1
Glomerulosclerosis, Focal Segmental A clinicopathological syndrome or diagnostic term for a type of glomerular injury that has multiple causes, primary or secondary. Clinical features include PROTEINURIA, reduced GLOMERULAR FILTRATION RATE, and EDEMA. Kidney biopsy initially indicates focal segmental glomerular consolidation (hyalinosis) or scarring which can progress to globally sclerotic glomeruli leading to eventual KIDNEY FAILURE.	0	4.62	1	1
Klebsiella Infections Infections with bacteria of the genus KLEBSIELLA.	0	4.99	2	1
Lung Neoplasms Tumors or cancer of the LUNG.	1	8.41	14	1
Mitral Valve Insufficiency Backflow of blood from the LEFT VENTRICLE into the LEFT ATRIUM due to imperfect closure of the MITRAL VALVE. This can lead to mitral valve regurgitation.	0	4.62	1	1
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.	0	4.62	1	1
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).	0	4.62	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.	0	4.62	1	1
Periodontal Pocket An abnormal extension of a gingival sulcus accompanied by the apical migration of the epithelial attachment and bone resorption.	0	4.62	1	1
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.	0	4.62	1	1
Precancerous Conditions Pathological conditions that tend eventually to become malignant.	0	5.27	4	1
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	0	12.31	14	4
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	0	7.74	4	4
Pulmonary Embolism Blocking of the PULMONARY ARTERY or one of its branches by an EMBOLUS.	0	4.62	1	1
Sarcoma A connective tissue neoplasm formed by proliferation of mesodermal cells; it is usually highly malignant.	0	4.85	2	1
Tobacco Use Disorder Tobacco used to the detriment of a person's health or social functioning. Tobacco dependence is included.	0	4.62	1	1
Vitiligo A disorder consisting of areas of macular depigmentation, commonly on extensor aspects of extremities, on the face or neck, and in skin folds. Age of onset is often in young adulthood and the condition tends to progress gradually with lesions enlarging and extending until a quiescent state is reached.	0	4.62	1	1
Osteoarthritis, Hip Noninflammatory degenerative disease of the hip joint which usually appears in late middle or old age. It is characterized by growth or maturational disturbances in the femoral neck and head, as well as acetabular dysplasia. A dominant symptom is pain on weight-bearing or motion.	0	4.62	1	1
Substance-Related Disorders Disorders related to substance use or abuse.	0	4.77	2	1
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)	0	4.62	1	1
Hearing Loss A general term for the complete or partial loss of the ability to hear from one or both ears.	0	4.62	1	1
Lipid Metabolism Disorders Pathological conditions resulting from abnormal anabolism or catabolism of lipids in the body.	0	4.62	1	1
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.	0	13.09	7	4
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.	0	4.82	2	1
Allergic Rhinitis [description not available]	0	2.66	2	0
Rhinitis, Allergic An inflammation of the NASAL MUCOSA triggered by ALLERGENS.	0	2.66	2	0
Cardiovascular Stroke [description not available]	0	3.14	5	0
Myocardial Infarction NECROSIS of the MYOCARDIUM caused by an obstruction of the blood supply to the heart (CORONARY CIRCULATION).	0	3.14	5	0
Metastase [description not available]	0	2.58	2	0
Experimental Mammary Neoplasms [description not available]	0	2.58	2	0
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	0	2.58	2	0
Anxiety Feelings or emotions of dread, apprehension, and impending disaster but not disabling as with ANXIETY DISORDERS.	0	3.38	6	0
Sore Throat [description not available]	0	2.25	1	0
Pharyngitis Inflammation of the throat (PHARYNX).	0	2.25	1	0
Bacterial Pneumonia [description not available]	0	2.25	1	0
Pneumonia, Bacterial Inflammation of the lung parenchyma that is caused by bacterial infections.	0	2.25	1	0
Clostridioides difficile Infection [description not available]	0	2.25	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.	0	2.98	3	0
Clostridium Infections Infections with bacteria of the genus CLOSTRIDIUM and closely related CLOSTRIDIOIDES species.	0	2.25	1	0
Carcinoma, Ductal, Pancreatic [description not available]	0	2.31	1	0
Carcinoma, Pancreatic Ductal Carcinoma that arises from the PANCREATIC DUCTS. It accounts for the majority of cancers derived from the PANCREAS.	0	2.31	1	0
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.	0	3.64	1	1
Hot Flashes A sudden, temporary sensation of heat predominantly experienced by some women during MENOPAUSE. (Random House Unabridged Dictionary, 2d ed)	0	3.64	1	1
Impaired Glucose Tolerance [description not available]	0	15.82	13	1
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.	1	12.82	13	1
Anxiety Neuroses [description not available]	0	2.5	2	0
Acute Post-Traumatic Stress Disorder [description not available]	0	2.31	1	0
Anxiety Disorders Persistent and disabling ANXIETY.	0	2.5	2	0
Stress Disorders, Post-Traumatic A class of traumatic stress disorders with symptoms that last more than one month.	0	2.31	1	0
Birnaviridae Infections Virus diseases caused by the BIRNAVIRIDAE.	0	2.31	1	0
Degenerative Disc Disease [description not available]	0	2.57	2	0
Intervertebral Disc Degeneration Degenerative changes in the INTERVERTEBRAL DISC due to aging or structural damage, especially to the vertebral end-plates.	0	7.57	2	0
Endomyometritis Inflammation of both the ENDOMETRIUM and the MYOMETRIUM, usually caused by infections after a CESAREAN SECTION.	0	2.31	1	0
Endometritis Inflammation of the ENDOMETRIUM, usually caused by intrauterine infections. Endometritis is the most common cause of postpartum fever.	0	7.31	1	0
Alpha Virus Infections [description not available]	0	2.31	1	0
Dermatitis Medicamentosa [description not available]	0	2.31	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.	0	2.31	1	0
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	0	2.95	4	0
Acute Edematous Pancreatitis [description not available]	0	2.61	2	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.	0	2.61	2	0
Adenoma, Prostatic [description not available]	0	2.15	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.	0	7.15	1	0
Deficiency Diseases A condition produced by dietary or metabolic deficiency. The term includes all diseases caused by an insufficient supply of essential nutrients, i.e., protein (or amino acids), vitamins, and minerals. It also includes an inadequacy of calories. (From Dorland, 27th ed; Stedman, 25th ed)	0	2.17	1	0
Anemia A reduction in the number of circulating ERYTHROCYTES or in the quantity of HEMOGLOBIN.	0	7.17	1	0
Dehydration The condition that results from excessive loss of water from a living organism.	0	2.15	1	0
Infections, Nematode [description not available]	0	2.15	1	0
Ovine Diseases [description not available]	0	2.15	1	0
Bile Duct Obstruction [description not available]	0	3.05	4	0
Cholestasis Impairment of bile flow due to obstruction in small bile ducts (INTRAHEPATIC CHOLESTASIS) or obstruction in large bile ducts (EXTRAHEPATIC CHOLESTASIS).	0	8.05	4	0
B16 Melanoma [description not available]	0	8	4	0
Infection, Wound [description not available]	0	2.59	2	0
Burns Injuries to tissues caused by contact with heat, steam, chemicals (BURNS, CHEMICAL), electricity (BURNS, ELECTRIC), or the like.	0	2.17	1	0
Neovascularization, Optic Disc [description not available]	0	2.55	2	0
Retinal Neovascularization Formation of new blood vessels originating from the retinal veins and extending along the inner (vitreal) surface of the retina.	0	2.55	2	0
Bone Loss, Osteoclastic [description not available]	0	2.52	2	0
Plica Syndrome [description not available]	0	2.17	1	0
Synovitis Inflammation of the SYNOVIAL MEMBRANE.	0	2.17	1	0
Diabetic Glomerulosclerosis [description not available]	0	2.55	2	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.	0	2.55	2	0
Hand Foot and Mouth Disease [description not available]	0	2.15	1	0
Hand, Foot and Mouth Disease A mild, highly infectious viral disease of children, characterized by vesicular lesions in the mouth and on the hands and feet. It is caused by coxsackieviruses A.	0	2.15	1	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.	0	2.76	3	0
Muscle Relaxation That phase of a muscle twitch during which a muscle returns to a resting position.	0	2.49	2	0
Extravascular Hemolysis [description not available]	0	4.1	14	0
Hemolysis The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.	0	4.1	14	0
Swine Diseases Diseases of domestic swine and of the wild boar of the genus Sus.	0	2.17	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.	0	2.17	1	0
Injuries, Knee [description not available]	0	2.17	1	0
Knee Injuries Injuries to the knee or the knee joint.	0	2.17	1	0
Lassitude [description not available]	0	2.17	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.	0	2.17	1	0
Eczema, Atopic [description not available]	0	3.08	5	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.	0	3.08	5	0
Grippe [description not available]	0	2.55	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.	0	2.55	2	0
Allergy, Egg [description not available]	0	2.17	1	0
Cognition Disorders Disorders characterized by disturbances in mental processes related to learning, thinking, reasoning, and judgment.	0	5.52	5	1
Colicky Pain [description not available]	0	2.52	2	0
Abdominal Pain Sensation of discomfort, distress, or agony in the abdominal region.	0	2.52	2	0
Palsy [description not available]	0	2.17	1	0
Paralysis A general term most often used to describe severe or complete loss of muscle strength due to motor system disease from the level of the cerebral cortex to the muscle fiber. This term may also occasionally refer to a loss of sensory function. (From Adams et al., Principles of Neurology, 6th ed, p45)	0	2.17	1	0
Infections, Pseudomonas [description not available]	0	2.61	2	0
Pseudomonas Infections Infections with bacteria of the genus PSEUDOMONAS.	0	2.61	2	0
Gastritis Inflammation of the GASTRIC MUCOSA, a lesion observed in a number of unrelated disorders.	0	2.51	2	0
Edema, Pulmonary [description not available]	0	2.21	1	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.	0	2.21	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.	0	4.07	3	1
Constriction, Pathological [description not available]	0	2.21	1	0
Constriction, Pathologic The condition of an anatomical structure's being constricted beyond normal dimensions.	0	2.21	1	0
Depression, Involutional Form of depression in those MIDDLE AGE with feelings of ANXIETY.	0	3.47	2	0
Depressive Disorder, Major Disorder in which five (or more) of the following symptoms have been present during the same 2-week period and represent a change from previous functioning; at least one of the symptoms is either (1) depressed mood or (2) loss of interest or pleasure. Symptoms include: depressed mood most of the day, nearly every daily; markedly diminished interest or pleasure in activities most of the day, nearly every day; significant weight loss when not dieting or weight gain; Insomnia or hypersomnia nearly every day; psychomotor agitation or retardation nearly every day; fatigue or loss of energy nearly every day; feelings of worthlessness or excessive or inappropriate guilt; diminished ability to think or concentrate, or indecisiveness, nearly every day; or recurrent thoughts of death, recurrent suicidal ideation without a specific plan, or a suicide attempt. (DSM-5)	0	3.47	2	0
Amyloid Deposits [description not available]	0	2.25	1	0
Health Care Associated Infection [description not available]	0	2.21	1	0
Cross Infection Any infection which a patient contracts in a health-care institution.	0	2.21	1	0
Anterior Choroidal Artery Infarction [description not available]	0	2.77	3	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).	0	2.77	3	0
Pyrexia [description not available]	0	2.46	2	0
Fever An abnormal elevation of body temperature, usually as a result of a pathologic process.	0	2.46	2	0
Itching [description not available]	0	2.48	2	0
Pruritus An intense itching sensation that produces the urge to rub or scratch the skin to obtain relief.	0	2.48	2	0
Lung Adenocarcinoma [description not available]	0	2.54	2	0
Adenocarcinoma, Basal Cell [description not available]	0	3.19	5	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.	0	2.54	2	0
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	0	3.19	5	0
Cancer of Cervix [description not available]	0	2.51	2	0
Cancer of Mouth [description not available]	0	2.44	2	0
Uterine Cervical Neoplasms Tumors or cancer of the UTERINE CERVIX.	0	2.51	2	0
Mouth Neoplasms Tumors or cancer of the MOUTH.	0	2.44	2	0
Cardiac Remodeling, Ventricular [description not available]	0	2.08	1	0
Hyperlipemia [description not available]	0	4.98	8	1
Hyperlipidemias Conditions with excess LIPIDS in the blood.	0	4.98	8	1
Acute Promyelocytic Leukemia [description not available]	0	7.08	1	0
Leukemia, Promyelocytic, Acute An acute myeloid leukemia in which abnormal PROMYELOCYTES predominate. It is frequently associated with DISSEMINATED INTRAVASCULAR COAGULATION.	0	2.08	1	0
Allergic Reaction [description not available]	0	8.58	9	0
Hypersensitivity Altered reactivity to an antigen, which can result in pathologic reactions upon subsequent exposure to that particular antigen.	0	8.58	9	0
Allodynia [description not available]	0	2.49	2	0
Nerve Pain [description not available]	0	2.49	2	0
Neuralgia Intense or aching pain that occurs along the course or distribution of a peripheral or cranial nerve.	0	2.49	2	0
Retinal Degeneration A retrogressive pathological change in the retina, focal or generalized, caused by genetic defects, inflammation, trauma, vascular disease, or aging. Degeneration affecting predominantly the macula lutea of the retina is MACULAR DEGENERATION. (Newell, Ophthalmology: Principles and Concepts, 7th ed, p304)	0	2.51	2	0
Bilateral Headache [description not available]	0	3.47	1	1
Headache The symptom of PAIN in the cranial region. It may be an isolated benign occurrence or manifestation of a wide variety of HEADACHE DISORDERS.	0	3.47	1	1
Pigmentary Retinopathy [description not available]	0	2.1	1	0
Retinitis Pigmentosa Hereditary, progressive degeneration of the retina due to death of ROD PHOTORECEPTORS initially and subsequent death of CONE PHOTORECEPTORS. It is characterized by deposition of pigment in the retina.	0	7.1	1	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)	0	3.6	8	0
Carbon Tetrachloride Poisoning Poisoning that results from ingestion, injection, inhalation, or skin absorption of CARBON TETRACHLORIDE.	0	2.1	1	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.	0	2.1	1	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.	0	2.1	1	0
Asymmetric Diabetic Proximal Motor Neuropathy [description not available]	0	2.77	3	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)	0	2.77	3	0
Food Poisoning, Staphylococcal [description not available]	0	2.1	1	0
Angiospasm, Intracranial [description not available]	0	2.1	1	0
Hemorrhage, Subarachnoid [description not available]	0	2.1	1	0
Subarachnoid Hemorrhage Bleeding into the intracranial or spinal SUBARACHNOID SPACE, most resulting from INTRACRANIAL ANEURYSM rupture. It can occur after traumatic injuries (SUBARACHNOID HEMORRHAGE, TRAUMATIC). Clinical features include HEADACHE; NAUSEA; VOMITING, nuchal rigidity, variable neurological deficits and reduced mental status.	0	2.1	1	0
Vasospasm, Intracranial Constriction of arteries in the SKULL due to sudden, sharp, and often persistent smooth muscle contraction in blood vessels. Intracranial vasospasm results in reduced vessel lumen caliber, restricted blood flow to the brain, and BRAIN ISCHEMIA that may lead to hypoxic-ischemic brain injury (HYPOXIA-ISCHEMIA, BRAIN).	0	2.1	1	0
Urinary Tract Infections Inflammatory responses of the epithelium of the URINARY TRACT to microbial invasions. They are often bacterial infections with associated BACTERIURIA and PYURIA.	0	3.48	1	1
Encephalopathy, Toxic [description not available]	0	3.76	3	0
Academic Disorder, Developmental [description not available]	0	2.48	2	0
Learning Disabilities Conditions characterized by a significant discrepancy between an individual's perceived level of intellect and their ability to acquire new language and other cognitive skills. These may result from organic or psychological conditions. Relatively common subtypes include DYSLEXIA, DYSCALCULIA, and DYSGRAPHIA.	0	2.48	2	0
Atheroma [description not available]	0	2.1	1	0
Hepatitis B Virus Infection [description not available]	0	7.81	3	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.	0	7.81	3	0
Urinary Calculi Low-density crystals or stones in any part of the URINARY TRACT. Their chemical compositions often include CALCIUM OXALATE, magnesium ammonium phosphate (struvite), CYSTINE, or URIC ACID.	0	2.1	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.	0	7.48	2	0
Endotoxin Shock [description not available]	0	2.11	1	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.	0	2.11	1	0
Pulmonary Hypertension [description not available]	0	2.11	1	0
Hypertension, Pulmonary Increased VASCULAR RESISTANCE in the PULMONARY CIRCULATION, usually secondary to HEART DISEASES or LUNG DISEASES.	0	2.11	1	0
Herpes Simplex Virus Infection [description not available]	0	2.11	1	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.)	0	2.11	1	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.	0	2.11	1	0
Anaphylactic Reaction [description not available]	0	8.32	6	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.	0	3.32	6	0
Incontinentia Pigmenti Achromians [description not available]	0	2.11	1	0
Sinus Infections [description not available]	0	2.11	1	0
Paranasal Sinus Diseases Diseases affecting or involving the PARANASAL SINUSES and generally manifesting as inflammation, abscesses, cysts, or tumors.	0	2.11	1	0
Sinusitis Inflammation of the NASAL MUCOSA in one or more of the PARANASAL SINUSES.	0	7.11	1	0
Central Nervous System Disease [description not available]	0	8.03	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.	0	8.03	1	0
Chromosome-Defective Micronuclei [description not available]	0	2.49	2	0
Bone Loss, Perimenopausal [description not available]	0	2.53	2	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.	0	2.53	2	0
Infections, Orthomyxoviridae [description not available]	0	2.13	1	0
Orthomyxoviridae Infections Virus diseases caused by the ORTHOMYXOVIRIDAE.	0	2.13	1	0
Cataract, Membranous [description not available]	0	2.99	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)	0	2.99	4	0
Antibody Deficiency Syndrome [description not available]	0	2.13	1	0
Immunologic Deficiency Syndromes Syndromes in which there is a deficiency or defect in the mechanisms of immunity, either cellular or humoral.	0	2.13	1	0
Overweight A status with BODY WEIGHT that is above certain standards. In the scale of BODY MASS INDEX, overweight is defined as having a BMI of 25.0-29.9 kg/m2. Overweight may or may not be due to increases in body fat (ADIPOSE TISSUE), hence overweight does not equal over fat.	0	6.56	3	2
Psychoses [description not available]	0	3.06	1	0
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)	0	3.06	1	0
Blood Pressure, Low [description not available]	0	3.51	1	1
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.	0	3.51	1	1
Pleurisy INFLAMMATION of PLEURA, the lining of the LUNG. When PARIETAL PLEURA is involved, there is pleuritic CHEST PAIN.	0	2.47	2	0
Erythema Redness of the skin produced by congestion of the capillaries. This condition may result from a variety of disease processes.	0	2.13	1	0
Clinically Isolated CNS Demyelinating Syndrome [description not available]	0	2.13	1	0
Demyelinating Diseases Diseases characterized by loss or dysfunction of myelin in the central or peripheral nervous system.	0	2.13	1	0
Wounds, Penetrating Wounds caused by objects penetrating the skin.	0	2.13	1	0
Hepatitis, Viral, Non-A, Non-B, Parenterally-Transmitted [description not available]	0	2.13	1	0
Hepatitis C INFLAMMATION of the LIVER in humans caused by HEPATITIS C VIRUS, a single-stranded RNA virus. Its incubation period is 30-90 days. Hepatitis C is transmitted primarily by contaminated blood parenterally and is often associated with transfusion and intravenous drug abuse. However, in a significant number of cases, the source of hepatitis C infection is unknown.	0	2.13	1	0
Hepatic Veno Occlusive Disease [description not available]	0	2.13	1	0
Hepatic Veno-Occlusive Disease Liver disease that is caused by injuries to the ENDOTHELIAL CELLS of the vessels and subendothelial EDEMA, but not by THROMBOSIS. Extracellular matrix, rich in FIBRONECTINS, is usually deposited around the HEPATIC VEINS leading to venous outflow occlusion and sinusoidal obstruction.	0	2.13	1	0
Aura [description not available]	0	2.13	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)	0	2.13	1	0
Primary Peritonitis [description not available]	0	2.13	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.	0	2.13	1	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.	0	2.13	1	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.	0	2.13	1	0
Thromboembolism, Venous [description not available]	0	2.15	1	0
Venous Thromboembolism Obstruction of a vein or VEINS (embolism) by a blood clot (THROMBUS) in the blood stream.	0	2.15	1	0
Gastroenteritis INFLAMMATION of any segment of the GASTROINTESTINAL TRACT from ESOPHAGUS to RECTUM. Causes of gastroenteritis are many including genetic, infection, HYPERSENSITIVITY, drug effects, and CANCER.	0	2.13	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.	0	2.13	1	0
Schistosoma japonicum Infection [description not available]	0	2.15	1	0
Arrhythmia [description not available]	0	2.15	1	0
Cardiac Diseases [description not available]	0	2.46	2	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.	0	2.15	1	0
Heart Diseases Pathological conditions involving the HEART including its structural and functional abnormalities.	0	2.46	2	0
Hepatitis, Animal INFLAMMATION of the LIVER in non-human animals.	0	2.15	1	0
Cochlear Hearing Loss [description not available]	0	2.15	1	0
Hearing Loss, Sensorineural Hearing loss resulting from damage to the COCHLEA and the sensorineural elements which lie internally beyond the oval and round windows. These elements include the AUDITORY NERVE and its connections in the BRAINSTEM.	0	2.15	1	0
Dermatitis Any inflammation of the skin.	0	2.38	2	0
Ascites Accumulation or retention of free fluid within the peritoneal cavity.	0	3.06	1	0
Hyperhomocysteinemia Condition in which the plasma levels of homocysteine and related metabolites are elevated (	0	2.15	1	0
Arthritides, Bacterial [description not available]	0	2.04	1	0
Alcohol Drinking Behaviors associated with the ingesting of ALCOHOLIC BEVERAGES, including social drinking.	0	2.05	1	0
Hepatitis, Viral, Animal INFLAMMATION of the LIVER in animals due to viral infection.	0	2.05	1	0
Infections, Hepadnaviridae [description not available]	0	2.05	1	0
Hepadnaviridae Infections Virus diseases caused by the HEPADNAVIRIDAE.	0	2.05	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)	0	2.44	2	0
Granulomas [description not available]	0	2.05	1	0
Granuloma A relatively small nodular inflammatory lesion containing grouped mononuclear phagocytes, caused by infectious and noninfectious agents.	0	2.05	1	0
Aortic Diseases Pathological processes involving any part of the AORTA.	0	2.05	1	0
Atopic Hypersensitivity [description not available]	0	2.88	4	0
Infections, Helicobacter [description not available]	0	2.05	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.	0	2.05	1	0
Choroid Neovascularization [description not available]	0	2.05	1	0
Injuries, Radiation [description not available]	0	2.05	1	0
Asthma, Bronchial [description not available]	0	2.05	1	0
Eosinophilia, Pulmonary [description not available]	0	2.05	1	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).	0	7.05	1	0
Pulmonary Eosinophilia A condition characterized by infiltration of the lung with EOSINOPHILS due to inflammation or other disease processes. Major eosinophilic lung diseases are the eosinophilic pneumonias caused by infections, allergens, or toxic agents.	0	7.05	1	0
Granulocytic Leukemia, Chronic [description not available]	0	2.44	2	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.	0	2.44	2	0
Amnesia-Memory Loss [description not available]	0	2.54	2	0
Amnesia Pathologic partial or complete loss of the ability to recall past experiences (AMNESIA, RETROGRADE) or to form new memories (AMNESIA, ANTEROGRADE). This condition may be of organic or psychologic origin. Organic forms of amnesia are usually associated with dysfunction of the DIENCEPHALON or HIPPOCAMPUS. (From Adams et al., Principles of Neurology, 6th ed, pp426-7)	0	7.54	2	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.	0	2.44	2	0
Intestinal Polyps Discrete abnormal tissue masses that protrude into the lumen of the INTESTINE. A polyp is attached to the intestinal wall either by a stalk, pedunculus, or by a broad base.	0	2.06	1	0
Arterial Obstructive Diseases [description not available]	0	2.06	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.	0	2.06	1	0
Cholera Infantum [description not available]	0	2.47	2	0
Allergy, Drug [description not available]	0	2.48	2	0
Drug Hypersensitivity Immunologically mediated adverse reactions to medicinal substances used legally or illegally.	0	2.48	2	0
Delayed Hypersensitivity [description not available]	0	2.07	1	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.	0	2.5	2	0
Autism [description not available]	0	2.07	1	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)	0	2.07	1	0
Food Poisoning [description not available]	0	2.06	1	0
Brain Swelling [description not available]	0	2.07	1	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)	0	2.07	1	0
Symptom Cluster [description not available]	0	2.08	1	0
Pelvic Pain Pain in the pelvic region of genital and non-genital origin.	0	2.08	1	0
Syndrome A characteristic symptom complex.	0	2.08	1	0
Absence Seizure [description not available]	0	2.9	4	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.	0	2.9	4	0
Diathesis [description not available]	0	2.01	1	0
Orthopedic Disorders [description not available]	0	1.93	1	0
Musculoskeletal Diseases Diseases of the muscles and their associated ligaments and other connective tissue and of the bones and cartilage viewed collectively.	0	1.93	1	0
Diseases of Immune System [description not available]	0	2.34	2	0
Immune System Diseases Disorders caused by abnormal or absent immunologic mechanisms, whether humoral, cell-mediated, or both.	0	2.34	2	0
Diseases, Occupational [description not available]	0	1.94	1	0
Respiratory Syndrome, Acute, Severe [description not available]	0	2.93	1	0
Severe Acute Respiratory Syndrome A viral disorder characterized by high FEVER, dry COUGH, shortness of breath (DYSPNEA) or breathing difficulties, and atypical PNEUMONIA. A virus in the genus CORONAVIRUS is the suspected agent.	0	2.93	1	0
Intertrochanteric Fractures [description not available]	0	8.98	9	0
Hip Fractures Fractures of the FEMUR HEAD; the FEMUR NECK; (FEMORAL NECK FRACTURES); the trochanters; or the inter- or subtrochanteric region. Excludes fractures of the acetabulum and fractures of the femoral shaft below the subtrochanteric region (FEMORAL FRACTURES).	0	8.98	9	0
Gastric Diseases [description not available]	0	2.03	1	0
Adenoma, beta-Cell [description not available]	0	2.03	1	0
Insulinoma A benign tumor of the PANCREATIC BETA CELLS. Insulinoma secretes excess INSULIN resulting in HYPOGLYCEMIA.	0	2.03	1	0
Brain Emboli [description not available]	0	2.03	1	0
Adenoma, Basal Cell [description not available]	0	1.96	1	0
Adenoma A benign epithelial tumor with a glandular organization.	0	1.96	1	0
Abnormalities, Autosome [description not available]	0	2.66	3	0
Cancer of the Tongue [description not available]	0	1.98	1	0
Tongue Neoplasms Tumors or cancer of the TONGUE.	0	1.98	1	0
Granulocytic Leukemia [description not available]	0	1.99	1	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.	0	1.99	1	0
Basophilic Leukemia, Acute [description not available]	0	2.7	3	0
Leukemia, Basophilic, Acute A rare acute myeloid leukemia in which the primary differentiation is to BASOPHILS. It is characterized by an extreme increase of immature basophilic granulated cells in the bone marrow and blood. Mature basophils are usually sparse.	0	2.7	3	0
Deficiency, Glucosephosphatase [description not available]	0	2.41	2	0
Glycogen Storage Disease Type I An autosomal recessive disease in which gene expression of glucose-6-phosphatase is absent, resulting in hypoglycemia due to lack of glucose production. Accumulation of glycogen in liver and kidney leads to organomegaly, particularly massive hepatomegaly. Increased concentrations of lactic acid and hyperlipidemia appear in the plasma. Clinical gout often appears in early childhood.	0	2.41	2	0
Cancer of Salivary Gland [description not available]	0	2	1	0
Salivary Gland Neoplasms Tumors or cancer of the SALIVARY GLANDS.	0	2	1	0
Coronary Heart Disease [description not available]	0	2.35	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.	0	2.35	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.	0	1.95	1	0
Experimental Hepatoma [description not available]	0	2.37	2	0
Hepatitis INFLAMMATION of the LIVER.	0	1.96	1	0
Leukemia L5178 An experimental lymphocytic leukemia of mice.	0	1.97	1	0
Cancer of Intestines [description not available]	0	1.96	1	0
Intestinal Neoplasms Tumors or cancer of the INTESTINES.	0	1.96	1	0
Fetal Death Death of the developing young in utero. BIRTH of a dead FETUS is STILLBIRTH.	0	1.95	1	0
Hydronephrosis Abnormal enlargement or swelling of a KIDNEY due to dilation of the KIDNEY CALICES and the KIDNEY PELVIS. It is often associated with obstruction of the URETER or chronic kidney diseases that prevents normal drainage of urine into the URINARY BLADDER.	0	1.95	1	0
Amyoplasia Congenita [description not available]	0	1.95	1	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.	0	1.95	1	0
Fatigue, Mental [description not available]	0	1.94	1	0
Infection [description not available]	0	1.95	1	0
Infections Invasion of the host organism by microorganisms or their toxins or by parasites that can cause pathological conditions or diseases.	0	1.95	1	0
Celiac Sprue [description not available]	0	2.86	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.	0	2.86	1	0
Eperythrozoonosis [description not available]	0	1.94	1	0
Cerebral Arteriosclerosis [description not available]	0	1.94	1	0
Intracranial Arteriosclerosis Vascular diseases characterized by thickening and hardening of the walls of ARTERIES inside the SKULL. There are three subtypes: (1) atherosclerosis with fatty deposits in the ARTERIAL INTIMA; (2) Monckeberg's sclerosis with calcium deposits in the media and (3) arteriolosclerosis involving the small caliber arteries. Clinical signs include HEADACHE; CONFUSION; transient blindness (AMAUROSIS FUGAX); speech impairment; and HEMIPARESIS.	0	1.94	1	0
Colitis, Granulomatous [description not available]	0	2.6	1	0
Crohn Disease A chronic transmural inflammation that may involve any part of the DIGESTIVE TRACT from MOUTH to ANUS, mostly found in the ILEUM, the CECUM, and the COLON. In Crohn disease, the inflammation, extending through the intestinal wall from the MUCOSA to the serosa, is characteristically asymmetric and segmental. Epithelioid GRANULOMAS may be seen in some patients.	0	2.6	1	0
Cachexia General ill health, malnutrition, and weight loss, usually associated with chronic disease.	0	2.25	1	0
Leukocytosis A transient increase in the number of leukocytes in a body fluid.	0	2.13	1	0
Autoimmune Diabetes [description not available]	0	2.11	1	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.	0	2.11	1	0
Heart Disease, Ischemic [description not available]	0	2.13	1	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).	0	2.13	1	0
Infections, Respiratory Syncytial Virus [description not available]	0	2.02	1	0
Respiratory Syncytial Virus Infections Pneumovirus infections caused by the RESPIRATORY SYNCYTIAL VIRUSES. Humans and cattle are most affected but infections in goats and sheep have been reported.	0	2.02	1	0

chlorogenic acid

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