protocatechuic acid profile

protocatechuic acid: RN given refers to parent cpd; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

3,4-dihydroxybenzoic acid : A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4. [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	72
CHEMBL ID	37537
CHEBI ID	36062
SCHEMBL ID	39435
MeSH ID	M0053486

Synonym
3,4-dihydroxy-benzoic acid
3, 4-dihydroxybenzoic acid
chebi:36062 ,
einecs 202-760-0
ccris 6291
brn 1448841
4,5-dihydroxybenzoic acid
protocatehuic acid
nsc 16631
nsc-16631
4-carboxy-1,2-dihydroxybenzene
mls000737807 ,
benzoic acid, 3,4-dihydroxy-
inchi=1/c7h6o4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9h,(h,10,11
99-50-3
protocatechuic acid
3,4-dihydroxybenzoic acid
protocatechuate
catechol-4-carboxylic acid
3,4-dihydroxybenzoic acid, >=97.0% (t)
976C8CCE-B25D-4E0A-9A6F-3CEEA7A6964F
pyrocatechol-4-carboxylic acid
ksc-10-128
KUC104409N
CHEMBL37537 ,
protacatechuic acid
BMSE000328
bdbm50100861
protocatechuic acid (m1)
cid_72
3,4-dihydroxybenzoate, viii
b-resorcylic acid
AKOS000119632
3,4-dihydroxybenzoate;3,4-dihydroxybenzoic acid
A846038
NCGC00246757-01
NCGC00246757-02
AE-562/40524392
tox21_200167
dtxsid4021212 ,
NCGC00257721-01
cas-99-50-3
dtxcid601212
BBL012232
STL163570
3,4-dihydroxy benzoic acid
HMS2270A17
S3975
hypogallic acid
36r5qj8l4b ,
unii-36r5qj8l4b
FT-0600028
AM20060767
4FHT
dihydroxybenzoic acid, 3,4-
fema no. 4430
protocatechuic acid [mi]
droxidopa metabolite (protocatechoic acid)
protocatechuic acid (pca)
3,4-dihydroxybenzoic acid [inci]
protocatechoic acid
protocatechoic acid (constituent of maritime pine) [dsc]
CCG-207950
SCHEMBL39435
mfcd00002509
CS-6092
HY-N0294
AC-9617
3,4-dihydroxybenzoic acid, analytical standard
protocatechuic acid, primary pharmaceutical reference standard
protocatechuic acid, united states pharmacopeia (usp) reference standard
b-resorcylate
beta-resorcylate
carbohydroquinonic acid
3,4-dihydroxybenzoic acid, vetec(tm) reagent grade, 97%
protocatechicacid
SY014104
Q418599
F11285
protocatechuic acid,(s)
1225528-47-1
AS-10808
zincselenite
EN300-21544
protocatechuicacid
Z104501142
protocatechoic acid (constituent of maritime pine)

Excerpt	Reference	Relevance
"Protocatechuic acid (PCA) is a naturally occurring phenolic acid with various biological and pharmacological activities."	( Protocatechuic acid attenuates lipopolysaccharide-induced septic lung injury in mice: The possible role through suppressing oxidative stress, inflammation and apoptosis. Abdel Moneim, AE; Albrakati, A; Alghamdi, AAA; Almalki, AA; Alsanie, WF; Alsharif, KF; Alzahrani, KJ; Bauomy, AA; Elshopakey, GE; Kabrah, SM; Kassab, RB; Lokman, MS; Ramadan, SS; Salem, FEH; Sberi, HA, 2021)	2.79
"Protocatechuic acid (PCA) is a biological agent with multiple functions."	( Protocatechuic acid protects mice from influenza A virus infection. Li, H; Li, Z; Ren, X; Wang, Q; Wang, X; Wu, J; Yang, L; Zhang, Y, 2022)	2.89
"Protocatechuic acid (PCA) is a natural polyphenol possessing anti-oxidant and anti-inflammatory activities."	( Pharmacological Postconditioning by Protocatechuic Acid Attenuates Brain Injury in Ischemia-Reperfusion (I/R) Mice Model: Implications of Nuclear Factor Erythroid-2-Related Factor Pathway. Grewal, AK; Khan, H; Kumar, M; Singh, TG, 2022)	1.72
"Protocatechuic acid (PCA) is an important phenolic compound with diverse industrial values. "	( Functional characterization of a new 3-dehydroshikimate dehydratase from Eupenicillium parvum and its potential for protocatechuic acid production. Ding, S; Lin, Q; Long, L; Wei, K, 2022)	2.37
"Protocatechuic acid (PCA) is a natural phenolic acid present in daily vegetables and fruits. "	( Protocatechuic Acid-Based Supramolecular Hydrogel Targets SerpinB9 to Achieve Local Chemotherapy for OSCC. Cao, L; Chen, Q; Li, Z; Liu, T; Luo, X; Yang, C; Zhao, H, 2022)	3.61
"Protocatechuic acid (PCA) is an important bioactive component of tea and has benefit to health."	( Protocatechuic Acid Delays Postovulatory Oocyte Ageing in Mouse. Chao, S; Ge, ZJ; Huang, GA; Li, LJ; Lu, J; Sun, QY; Yin, S; Zhang, XY; Zhao, L; Zhao, MH; Zhao, SX; Zhao, Y, 2023)	3.07
"Protocatechuic acid (PCA) is a polyphenolic compound with various potent biological activities."	( Protocatechuic acid reverses myocardial infarction mediated by β-adrenergic agonist via regulation of Nrf2/HO-1 pathway, inflammatory, apoptotic, and fibrotic events. Elhefny, MA; Jiang, H; Kassab, RB; Li, L; Lokman, MS; Ma, H; Sberi, HA; Xia, B; Zhang, Y, 2023)	3.07
"Protocatechuic acid (PCA) is a potent Sirt1 activator and exhibits antioxidant as well as anti-inflammatory properties."	( Impact of protocatechuic acid on alleviation of pulmonary damage induced by cyclophosphamide targeting peroxisome proliferator activator receptor, silent information regulator type-1, and fork head box protein in rats. Amin, MM; Elgohary, R; Elwahab, SA; Salama, A, 2023)	2.03
"Protocatechuic acid (PCA) is a natural component with multiple biological activities. "	( Protocatechuic Acid Alleviates Dextran-Sulfate-Sodium-Induced Ulcerative Colitis in Mice via the Regulation of Intestinal Flora and Ferroptosis. Hu, S; Li, L; Sun, X; Tan, Y; Xiao, S; Yang, X; Zhong, L; Zhou, F; Zhou, Z, 2023)	3.8
"Protocatechuic acid is a phenol-rich compound derived from herbs and owns vital functions in numerous diseases."	( Protocatechuic acid alleviates polycystic ovary syndrome symptoms in mice by PI3K signaling in granulosa cells to relieve ROS pressure and apoptosis. Nie, X; Tan, Y; Tong, X; Tong, Y; Wang, F; Yin, Y; Zhou, J; Zou, Y, 2023)	3.07
"Protocatechuic acid (PA) is a polyphenol-recognized for its efficacy as an antioxidant-possesses anticancer, anti-inflammatory, antioxidant properties. "	( Protocatechuic acid ameliorates testosterone-induced benign prostatic hyperplasia through the regulation of inflammation and oxidative stress in castrated rats. Abiola, OJ; Adaramoye, OA; Adeyanju, AA; Akanni, OO; Olowofela, OG; Owumi, SE, 2020)	3.44
"Protocatechuic acid (PCA) is a phenolic acid metabolite of the parent anthocyanin, kuromanin, found in blackberries and bilberries."	( Protocatechuic Acid Extends Survival, Improves Motor Function, Diminishes Gliosis, and Sustains Neuromuscular Junctions in the hSOD1 Baybayon-Grandgeorge, AN; Holsopple, J; Koza, LA; Linseman, DA; Mazzarino, RC; Olson, JR; Patterson, D; Pena, C; Winter, AN, 2020)	2.72
"Protocatechuic acid is a natural phenolic acid, which widely exists in our daily diet and herbs. "	( New progress in the pharmacology of protocatechuic acid: A compound ingested in daily foods and herbs frequently and heavily. Ci, Z; Feng, B; Han, L; He, Y; Luo, C; Ran, F; Song, J; Xu, H; Xu, R; Zhang, D, 2020)	2.28
"Protocatechuic acid (PCA) is a phenolic acid been proved neuroprotection in ICH without understanding of details."	( Protocatechuic Acid Suppresses Microglia Activation and Facilitates M1 to M2 Phenotype Switching in Intracerebral Hemorrhage Mice. Bian, L; Chen, X; Sun, Q; Sun, Y; Wang, B; Xi, Z; Xu, C; Zhong, Z, 2021)	2.79
"Protocatechuic acid (PCA) is a natural secondary metabolite commonly found in fruits, vegetables, grains, and herbal medicine."	( Research progress on intervention effect and mechanism of protocatechuic acid on nonalcoholic fatty liver disease. Gao, Y; Han, S; Huang, W; Ji, L; Liu, H; Tian, R; Xue, H; You, Y; Zhan, J; Zhang, R, 2022)	1.69
"Protocatechuic acid (PCA) is a phenolic compound found in many antiviral Chinese herbal medicines. "	( Protocatechuic acid inhibits hepatitis B virus replication by activating ERK1/2 pathway and down-regulating HNF4α and HNF1α in vitro. Cai, WT; Chen, Y; Dai, XQ; Han, FM; Wu, X, 2017)	3.34
"Protocatechuic acid (PCA) is an antiviral agent against Avian Influenza virus (AIV) and Infectious Bursal Disease (IBD) virus, but its antiviral mechanism is unknown. "	( Protocatechuic acid (PCA) induced a better antiviral effect by immune enhancement in SPF chickens. Chu, J; Guo, Y; He, C; Javed, MT; Xiao, H; Zhang, Q; Zuo, Z, 2018)	3.37
"Protocatechuic acid (PCA) is a type of phenolic acid found in green tea and has been shown to have potent antioxidant and anti-inflammatory properties. "	( Protective Effects of Protocatechuic Acid on Seizure-Induced Neuronal Death. Choi, BY; Choi, HC; Hong, DK; Jeong, JH; Kho, AR; Lee, MW; Lee, SH; Lee, SY; Song, HK; Suh, SW, 2018)	2.24
"Protocatechuic acid (PCA) is a natural antioxidant with beneficial cardiovascular properties. "	( Antihypertensive and antioxidant effects of protocatechuic acid in deoxycorticosterone acetate-salt hypertensive rats. Emami, R; Haghighatian, Z; Hajhashemi, V; Safaeian, L, 2018)	2.18
"Protocatechuic acid (PCA) is a major metabolite of the antioxidant polyphenols, which have been discovered in green tea."	( Effects of Protocatechuic Acid (PCA) on Global Cerebral Ischemia-Induced Hippocampal Neuronal Death. Choi, BY; Choi, HC; Hong, DK; Jeong, JH; Kho, AR; Lee, SH; Park, KH; Song, HK; Suh, SW, 2018)	1.59
"Protocatechuic acid (PCA) is a phenolic phytochemical widely reported to possess antidiabetic property."	( Protocatechuic acid ameliorates neurobehavioral deficits via suppression of oxidative damage, inflammation, caspase-3 and acetylcholinesterase activities in diabetic rats. Adedara, IA; Ajayi, OM; Ayeni, MF; Farombi, EO; Fasina, OB, 2019)	2.68
"Protocatechuic acid (PCA) is a phenolic compound believed to have neuroprotective and procognitive activity. "	( Administration of protocatechuic acid affects memory and restores hippocampal and cortical serotonin turnover in rat model of oral D-galactose-induced memory impairment. Blecharz-Klin, K; Joniec-Maciejak, I; Krzysztoforska, K; Mirowska-Guzel, D; Piechal, A; Pyrzanowska, J; Widy-Tyszkiewicz, E, 2019)	2.29
"Protocatechuic acid is an antioxidant which is shown to have analgesic activity in limited studies. "	( Cannabinoid system involves in the analgesic effect of protocatechuic acid. Arslan, R; Bektas, N; Dikmen, DY; Okcay, Y, 2019)	2.2
"Protocatechuic acid (PCA) is a phenolic compound, a main metabolite of anthocyanin, which has been reported to display various pharmacological properties."	( Protocatechuic acid exerts a cardioprotective effect in type 1 diabetic rats. Chattipakorn, N; Chattipakorn, SC; Kumfu, S; Pannangpetch, P; Semaming, Y, 2014)	2.57
"Protocatechuic acid (PCA) is a dihydroxybenzoic acid, a type of phenolic acid, isolated from the kernels of Alpinia oxyphylla Miq (AOF), a traditional Chinese herbal medicine the fruits of which are widely used as a tonic, aphrodisiac, anti-salivation and anti-diarrheatic."	( Nerve Regeneration Potential of Protocatechuic Acid in RSC96 Schwann Cells by Induction of Cellular Proliferation and Migration through IGF-IR-PI3K-Akt Signaling. Chung, LC; Day, CH; Ho, TJ; Huang, CY; Ju, DT; Liao, HE; Lin, CC; Padma, VV; Shibu, MA; Tsai, FJ, 2015)	1.42
"Protocatechuic acid (PCA) is a main metabolite of anthocyanins, whose daily intake is much higher than that of other polyphenols. "	( Protocatechuic acid induces antioxidant/detoxifying enzyme expression through JNK-mediated Nrf2 activation in murine macrophages. Carotenuto, S; D'Archivio, M; Filesi, C; Giovannini, C; Masella, R; Santangelo, C; Scazzocchio, B; Varì, R, 2011)	3.25
"Protocatechuic acid (PCA) is a major metabolite of anthocyanins. "	( Protocatechuic acid attenuates lipolysaccharide-induced acute lung injury. Cai, Q; Chu, X; Ci, X; Deng, X; Guan, M; Jiang, L; Liu, J; Wei, M; Yang, X; Zheng, C, 2012)	3.26

Excerpt	Reference	Relevance
"Protocatechuic acid (PCA) has a protective effect on alcoholic liver injury, but the role of PCA in type 2 diabetes-induced liver injury is not well known."	( Hepatoprotective effect of protocatechuic acid against type 2 diabetes-induced liver injury. Chen, S; Feng, Q; Lu, G; Wang, Y; Xu, K, 2023)	2.65
"Protocatechuic acid has a wide range of pharmacological activities including antioxidant, anti-inflammatory, neuroprotective, antibacterial, antiviral, anticancer, antiosteoporotic, analgesia, antiaging activties; protection from metabolic syndrome; and preservation of liver, kidneys, and reproductive functions."	( New progress in the pharmacology of protocatechuic acid: A compound ingested in daily foods and herbs frequently and heavily. Ci, Z; Feng, B; Han, L; He, Y; Luo, C; Ran, F; Song, J; Xu, H; Xu, R; Zhang, D, 2020)	1.55
"Protocatechuic acid (PCA) has been shown to possess anti-inflammatory and anti-bacterial functions."	( Dietary protocatechuic acid ameliorates ileal mucosal barrier injury and inflammatory response and improves intestinal microbiota composition in Yellow chickens challenged with Salmonella typhimurium. Cui, X; Gou, Z; Jiang, S; Wang, Y; Zhang, S, 2023)	2.07
"Protocatechuic acid (PCA) has a protective effect on alcoholic liver injury, but the role of PCA in type 2 diabetes-induced liver injury is not well known."	( Hepatoprotective effect of protocatechuic acid against type 2 diabetes-induced liver injury. Chen, S; Feng, Q; Lu, G; Wang, Y; Xu, K, 2023)	2.65
"Protocatechuic acid has a wide range of pharmacological activities including antioxidant, anti-inflammatory, neuroprotective, antibacterial, antiviral, anticancer, antiosteoporotic, analgesia, antiaging activties; protection from metabolic syndrome; and preservation of liver, kidneys, and reproductive functions."	( New progress in the pharmacology of protocatechuic acid: A compound ingested in daily foods and herbs frequently and heavily. Ci, Z; Feng, B; Han, L; He, Y; Luo, C; Ran, F; Song, J; Xu, H; Xu, R; Zhang, D, 2020)	1.55
"Protocatechuic acid (PCA) has been proved possessing neuroprotection in ICH."	( Protocatechuic acid attenuates brain edema and blood-brain barrier disruption after intracerebral hemorrhage in mice by promoting Nrf2/HO-1 pathway. Bian, L; Chen, X; Sun, Q; Sun, Y; Wang, B; Xi, Z; Xu, C; Zhong, Z, 2020)	2.72
"Protocatechuic acid (PCA) has been widely utilized in conventional pharmaceutical, cosmetic and functional food industries. "	( Metabolic engineering of Pseudomonas putida KT2440 for high-yield production of protocatechuic acid. Li, J; Ye, BC, 2021)	2.29
"Protocatechuic acid has very promising properties potentially useful in the inhibition of neurodegenerative diseases progression. "	( Pharmacological effects of protocatechuic acid and its therapeutic potential in neurodegenerative diseases: Review on the basis of Krzysztoforska, K; Mirowska-Guzel, D; Widy-Tyszkiewicz, E, 2019)	2.25
"Protocatechuic acid has demonstrated to have antioxidant and anti-inflammatory effects. "	( Protocatechuic acid inhibits Toll-like receptor-4-dependent activation of NF-κB by suppressing activation of the Akt, mTOR, JNK and p38-MAPK. Lee, CS; Nam, YJ, 2018)	3.37
"Protocatechuic acid (PCA) has been well studied for its neuroprotection value in several diseases, but the effect in intracerebral haemorrhage (ICH) has not been reported. "	( Protocatechuic acid exerts protective effects via suppression of the P38/JNK- NF-κB signalling pathway in an experimental mouse model of intracerebral haemorrhage. Bian, L; Chen, X; Hu, X; Ren, J; Sun, Q; Sun, Y; Wang, B; Xi, Z; Yang, GY; Yang, Y; Zhong, Z, 2019)	3.4
"Protocatechuic acid has reported containing antioxidant effects. "	( Anti-skin aging properties of protocatechuic acid in vitro and in vivo. Cho, SH; Jung, E; Park, D; Shin, S, 2020)	2.29
"Protocatechuic acid (PCA), which has been widely studied as a polyphenolic compound, induces expression of antioxidative genes that combat oxidative stress and cell apoptosis."	( Modulating the p66shc signaling pathway with protocatechuic acid protects the intestine from ischemia-reperfusion injury and alleviates secondary liver damage. Chang, H; Chen, Z; Li, Z; Ma, L; Ma, Z; Tian, X; Wang, G; Wang, S; Yao, J; Zhao, H, 2014)	1.38
"Protocatechuic acid (PCA) has been implicated in the progression of atherosclerosis. "	( Protocatechuic acid inhibits oleic acid-induced vascular smooth muscle cell proliferation through activation of AMP-activated protein kinase and cell cycle arrest in G0/G1 phase. Chan, KC; Chang, CH; Lin, MC; Ou, TT; Wang, CJ, 2015)	3.3
"Protocatechuic acid (PCA) has been reported to exert antioxidant and anti-hyperglycemic activities."	( Protocatechuic Acid Restores Vascular Responses in Rats With Chronic Diabetes Induced by Streptozotocin. Kongyingyoes, B; Kukongviriyapan, U; Pannangpetch, P; Semaming, Y; Thukhammee, W, 2016)	2.6
"Protocatechuic acid (PCA), which has antioxidant property, is a simple phenolic compound commonly found in many plants, vegetables, and fruits, notably in green tea and almonds. "	( Does protocatechuic acid, a natural antioxidant, reduce renal ischemia reperfusion injury in rats? Akşit, D; Akşit, H; Aslan, F; Başbuğ, M; Çavdar, F; Çıkman, Ö; Yıldar, M; Yüksel, M, 2017)	2.41
"Protocatechuic acid (PCA) has been isolated from the leaves of ilex chinenses and has numerous pharmacologic effects, including anti-inflammatory and antitumoral activities. "	( Protocatechuic acid suppresses ovalbumin-induced airway inflammation in a mouse allergic asthma model. Chen, C; Chu, X; Deng, X; Guan, M; Liu, F; Wei, M; Xie, X; Yang, X, 2013)	3.28
"Protocatechuic acid has antioxidant activity."	( Protective effect of protocatechuic acid isopropyl ester against murine models of sepsis: inhibition of TNF-alpha and nitric oxide production and augmentation of IL-10. Hong, YJ; Jung, JS; Kim, YH; Moon, YS; Song, DK; Suh, HW; Yan, JJ; Yun-Choi, HS, 2004)	1.36

Excerpt	Reference	Relevance
"Protocatechuic acid (PCA) plays a critical role in nutritional metabolism; it is a major metabolite of anthocyanins, which are flavonoids with a range of health benefits. "	( Protocatechuic Acid Attenuates Osteoclastogenesis by Downregulating JNK/c-Fos/NFATc1 Signaling and Prevents Inflammatory Bone Loss in Mice. Ahn, SJ; Baek, JM; Cheon, YH; Kim, JY; Lee, MS; Oh, J; Park, SH; Yoon, KH, 2016)	3.32

Excerpt	Reference	Relevance
"Protocatechuic acid treatment reversed these effects."	( Protocatechuic acid attenuates isoproterenol-induced cardiac hypertrophy via downregulation of ROCK1-Sp1-PKCγ axis. Bai, L; Han, X; Jeong, MH; Kee, HJ; Kee, SJ; Zhao, T, 2021)	2.79
"Protocatechuic acid treatment significantly decreased (P < 0.05) ST-induced proinflammatory cytokine (Interleukin-1β, Interleukin-6, Tumor necrosis factor-α, and Interferon-β) content in ileum."	( Dietary protocatechuic acid ameliorates ileal mucosal barrier injury and inflammatory response and improves intestinal microbiota composition in Yellow chickens challenged with Salmonella typhimurium. Cui, X; Gou, Z; Jiang, S; Wang, Y; Zhang, S, 2023)	2.07
"Protocatechuic acid treatment or transfection with short-interfering RNA against Kmo ameliorated transforming growth factor β1-induced upregulation of Kmo, Col1a1, Col1a2 and Fn1 in vivo or in neonatal rat cardiac fibroblasts."	( Protocatechuic acid prevents isoproterenol-induced heart failure in mice by downregulating kynurenine-3-monooxygenase. Bai, L; Han, X; He, X; Jeon, MJ; Jeong, MH; Jeong, SM; Kee, HJ; Kee, SJ; Kim, SH; Zhou, H, 2023)	3.07
"Protocatechuic acid treatment minimally reduced the MC-induced EROD and MROD, but the observed differences were statistically significant."	( Modulation of 3-methylcholanthrene-induced rat hepatic and renal cytochrome P450 and phase II enzymes by plant phenols: protocatechuic and tannic acids. Baer-Dubowska, W; Krajka-Kuźniak, V; Szaefer, H, 2004)	1.04
"The treatment with protocatechuic acid alone enhanced slightly the activities of all three phase II enzymes in liver."	( Modulation of 3-methylcholanthrene-induced rat hepatic and renal cytochrome P450 and phase II enzymes by plant phenols: protocatechuic and tannic acids. Baer-Dubowska, W; Krajka-Kuźniak, V; Szaefer, H, 2004)	0.64
"Pretreatment with protocatechuic acid isopropyl ester effectively suppressed the LPS/GalN-induced increase in plasma tumor necrosis factor (TNF)-alpha alanine aminotransferase (ALT), nitrite/nitrate levels, and hepatic malondialdehyde levels."	( Protective effect of protocatechuic acid isopropyl ester against murine models of sepsis: inhibition of TNF-alpha and nitric oxide production and augmentation of IL-10. Hong, YJ; Jung, JS; Kim, YH; Moon, YS; Song, DK; Suh, HW; Yan, JJ; Yun-Choi, HS, 2004)	0.97

Excerpt	Reference	Relevance
" Although not toxic to wild-type cells initially, the diphenolic caffeate was itself converted to a toxin over time in the absence of cells; the converted toxin was bactericidal."	( Toxicity caused by hydroxycinnamoyl-coenzyme A thioester accumulation in mutants of Acinetobacter sp. strain ADP1. Ornston, LN; Parke, D, 2004)	0.32
" Although this study is far from the demonstration of a toxic effect of the tested bioactives when administered to humans, it represents a starting point for future research aimed at verifying the existence of a potential hazard due to the wide use of high doses of multiple bioactives."	( Is cytotoxicity a determinant of the different in vitro and in vivo effects of bioactives? Bordoni, A; Danesi, F; Di Nunzio, M; Murgui-Bosch, L; Tomás-Chisbert, T; Tomás-Cobos, L; Valli, V, 2017)	0.46

Excerpt	Reference	Relevance
"0 software to calculate the pharmacokinetic parametes."	( [Effects of borneol on pharmacokinetics of protocatechuic acid in rabbits]. Lan, W; Liu, C; Wang, S; Yang, J; Zheng, X, 2009)	0.62
" Pharmacokinetic parameters were estimated using non-compartmental methods."	( Pharmacokinetics of phenolic compounds of Danshen extract in rat blood and brain by microdialysis sampling. Li, J; Wu, L; Yin, FX; Yuan, Y; Zhang, QL; Zhang, YJ, 2011)	0.37
" The main pharmacokinetic parameters of GA and PCA were obtained based on the analysis of the plasma sample by non-compartmental analysis."	( An UHPLC-MS/MS method for simultaneous quantification of gallic acid and protocatechuic acid in rat plasma after oral administration of Polygonum capitatum extract and its application to pharmacokinetics. Gong, X; Li, M; Ma, F; Zhao, Y; Zhou, X, 2015)	0.65
" Pharmacokinetic parameters for GA and PCA following oral administration of the extract were respectively: Cmax 246."	( An UHPLC-MS/MS method for simultaneous quantification of gallic acid and protocatechuic acid in rat plasma after oral administration of Polygonum capitatum extract and its application to pharmacokinetics. Gong, X; Li, M; Ma, F; Zhao, Y; Zhou, X, 2015)	0.65
" capitatum extract may be metabolized to GA, which affected the pharmacokinetic profiles of GA."	( An UHPLC-MS/MS method for simultaneous quantification of gallic acid and protocatechuic acid in rat plasma after oral administration of Polygonum capitatum extract and its application to pharmacokinetics. Gong, X; Li, M; Ma, F; Zhao, Y; Zhou, X, 2015)	0.65
"A very simple and selective high-performance liquid chromatography electrospray ionization tandem mass spectrometry (LC-MS-MS) method was developed for simultaneous determination and pharmacokinetic study of protocatechuic aldehyde (PAL) and its active metabolite protocatechuic acid (PCA)."	( Simultaneous Determination and Pharmacokinetic Study of Protocatechuic Aldehyde and Its Major Active Metabolite Protocatechuic Acid in Rat Plasma by Liquid Chromatography-Tandem Mass Spectrometry. Chu, Y; Guo, J; Li, S; Li, W; Liu, C; Ma, X; Wang, X; Yan, K; Zhou, S; Zhu, Y, )	0.52
"To develop a sensitive and reliable ultra performance liquid chromatography tandem mass spectrometry ( UPLC-MS / MS) method for simultaneous determination and pharmacokinetics of protocatechuic acid, kaempferol biotin glucoside and quercitrin in rat plasma, and study their pharmacokinetic characteristics in rats."	( [Simultaneous Determination of Protocatechuic Acid,Kaempferol Biotin Glucoside and Quercitrin in Rat Plasma and Pharmacokinetics By UPLC-MS/MS]. Chen, SY; Li, YJ; Sun, J; Xiang, WY; Yang, W; Zheng, L, 2016)	0.91
"The established method is specific,rapid,accurate and sensitive,and is proved to meet the requirements of biological sample analyses,and is suitable for the concentration determination of protocatechuic acid, kaempferol biotin glucoside and quercitrin in rat plasma, three compounds are all best fitted to the two-compartment open pharmacokinetic model."	( [Simultaneous Determination of Protocatechuic Acid,Kaempferol Biotin Glucoside and Quercitrin in Rat Plasma and Pharmacokinetics By UPLC-MS/MS]. Chen, SY; Li, YJ; Sun, J; Xiang, WY; Yang, W; Zheng, L, 2016)	0.91
"GA and PCA were absorbed into the blood within 1 h after administration and rapidly eliminated with a half-life of less than 2 h."	( Pharmacokinetics of gallic acid and protocatechuic acid in humans after dosing with Relinqing (RLQ) and the potential for RLQ-perpetrated drug-drug interactions on organic anion transporter (OAT) 1/3. Cao, Y; Du, X; Huang, Y; Li, Y; Li, Z; Liu, C; Sun, J; Wang, B; Wang, R; Wu, W, 2021)	0.9
"GA and PCA are recommended as PK-markers in RLQ-related pharmacokinetic and drug interaction studies."	( Pharmacokinetics of gallic acid and protocatechuic acid in humans after dosing with Relinqing (RLQ) and the potential for RLQ-perpetrated drug-drug interactions on organic anion transporter (OAT) 1/3. Cao, Y; Du, X; Huang, Y; Li, Y; Li, Z; Liu, C; Sun, J; Wang, B; Wang, R; Wu, W, 2021)	0.9

Excerpt	Reference	Relevance
"Relinqing granules (RLQ) are being used alone or in combination with antibacterial drugs to treat urological disorders."	( Pharmacokinetics of gallic acid and protocatechuic acid in humans after dosing with Relinqing (RLQ) and the potential for RLQ-perpetrated drug-drug interactions on organic anion transporter (OAT) 1/3. Cao, Y; Du, X; Huang, Y; Li, Y; Li, Z; Liu, C; Sun, J; Wang, B; Wang, R; Wu, W, 2021)	0.9

Excerpt	Reference	Relevance
" Our results suggested that low molecular weight polyphenols are absorbed in the intestine and metabolized to their glucuronide conjugates, which exhibit antioxidative activity in plasma, and that TA can enhance the bioavailability of wine polyphenols."	( Absorption and metabolism of antioxidative polyphenolic compounds in red wine. Harada, M; Kiso, Y; Koda, H; Sakane, T; Sezaki, H; Sugiura, N; Yamashita, S, 2002)	0.31
" However, one consistent result of these studies is that the systemic bioavailability of anthocyanins, including cyanidin 3-O-glucopyranoside (Cy-3G), is very poor."	( Neuroprotective effects of anthocyanins and their in vivo metabolites in SH-SY5Y cells. Angeloni, C; Cantelli-Forti, G; Hrelia, P; Hrelia, S; Marchesi, A; Morroni, F; Tarozzi, A, 2007)	0.34
" Borneol could improve the bioavailability of PA."	( [Effects of borneol on pharmacokinetics of protocatechuic acid in rabbits]. Lan, W; Liu, C; Wang, S; Yang, J; Zheng, X, 2009)	0.62
" Due to the poor understanding of the bioavailability of anthocyanins, the potential antiatherogenic mechanisms underlying the action remain largely unknown."	( Cyanidin-3-O-β-glucoside with the aid of its metabolite protocatechuic acid, reduces monocyte infiltration in apolipoprotein E-deficient mice. Ling, W; Wang, D; Yan, X; Yang, Y; Zou, T, 2011)	0.62
"Anthocyanins are being increasingly investigated for their neuroprotective and antineuroinflammatory effects; however, the overall bioavailability of many anthocyanins is relatively low."	( Comparison of the Neuroprotective and Anti-Inflammatory Effects of the Anthocyanin Metabolites, Protocatechuic Acid and 4-Hydroxybenzoic Acid. Arora, Y; Brenner, MC; Byars, C; Linseman, DA; Punessen, N; Snodgrass, M; Winter, AN, 2017)	0.67
"Previous studies indicated that cyanidin-3-O-β-glucoside (C3G) as a classical anthocyanin exerted an anti-fibrotic effect in the liver, but its bioavailability was quite low."	( Cyanidin-3-O-β-glucoside combined with its metabolite protocatechuic acid attenuated the activation of mice hepatic stellate cells. Guo, H; Jiang, X; Ling, W; Shen, T; Tang, X; Yang, W, 2017)	0.7
" 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
" These phytochemicals are poorly absorbed and may be transformed by gut microbiota into various metabolites that may impact the colonic mucosa or upon absorption have systemic bioactivity."	( Dietary Black Raspberries Impact the Colonic Microbiome and Phytochemical Metabolites in Mice. Bailey, MT; Clinton, SK; Gu, J; Riedl, KM; Schwartz, SJ; Thomas-Ahner, JM; Vodovotz, Y, 2019)	0.51
" Feeding black raspberries inhibited mammary cancer induction in rats and growth of cancer cells in nude mice, indicating systemic bioavailability of bioactive compounds."	( Effects of Black Raspberries and Their Constituents on Rat Prostate Carcinogenesis and Human Prostate Cancer Cell Growth In Vitro. Bosland, MC; Dodge, A; Eskra, JN; Schlicht, MJ, 2020)	0.56
"Current mechanism studies in plant heavy metal tolerance do not consider the effects of different phenolic acids on the bioavailability of heavy metals and the comparison with antioxidant enzyme system in the hydroxyl radical scavenging capacity."	( Effects of phenolic acids on free radical scavenging and heavy metal bioavailability in kandelia obovata under cadmium and zinc stress. Chen, S; Lin, R; Liu, J; Lu, H; Wang, Q; Yan, C; Yang, J, 2020)	0.56

Excerpt	Relevance	Reference
" These rats were fed diet containing 1000 or 2000 ppm PCA for 5 weeks, starting one week before the first dosing of AOM."	( Suppression of azoxymethane-induced rat colon aberrant crypt foci by dietary protocatechuic acid. Kawamori, T; Kojima, T; Mori, H; Ohnishi, M; Suzui, M; Tanaka, T, 1994)	0.52
" Dose-response studies using the pure compounds indicated that caffeic acid was the most active antioxidant with an IC50 < 1 mumol/l for copper-initiated low-density lipoprotein oxidation."	( Phenolic content of various beverages determines the extent of inhibition of human serum and low-density lipoprotein oxidation in vitro: identification and mechanism of action of some cinnamic acid derivatives from red wine. Abu-Amsha, R; Beilin, LJ; Croft, KD; Proudfoot, JM; Puddey, IB, 1996)	0.29
"5 mmol/kg dosed by gavage) for 5 days significantly decreased the serum levels of the hepatic enzyme markers alanine- and aspartate aminotransferase (ALT, alanine aminotransferase; AST, aspartate aminotransferase) induced by the 6-h treatment with LPS (i."	( Hibiscus protocatechuic acid inhibits lipopolysaccharide-induced rat hepatic damage. Cheng, MT; Chou, FP; Hsieh, YJ; Lin, WL; Tseng, TH; Wang, CJ, 2003)	0.74
" Utilizing DoE we systematically modified biosensor dose-response behavior by increasing the maximum signal output (up to 30-fold increase), improving dynamic range (>500-fold), expanding the sensing range (∼4-orders of magnitude), increasing sensitivity (by >1500-fold), and modulated the slope of the curve to afford biosensors designs with both digital and analogue dose-response behavior."	( Development of High-Performance Whole Cell Biosensors Aided by Statistical Modeling. Berepiki, A; Dixon, N; Kent, R; Machado, LFM, 2020)	0.56

Role	Description
human xenobiotic metabolite	Any human metabolite produced by metabolism of a xenobiotic compound in humans.
plant metabolite	Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
antineoplastic agent	A substance that inhibits or prevents the proliferation of neoplasms.
EC 1.1.1.25 (shikimate dehydrogenase) inhibitor	An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of shikimate dehydrogenase (EC 1.1.1.25).
EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor	An EC 1.14.11.* (oxidoreductase acting on paired donors, 2-oxoglutarate as one donor, incorporating 1 atom each of oxygen into both donors) inhibitor that interferes with the action of procollagen-proline dioxygenase (EC 1.14.11.2).
[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
dihydroxybenzoic acid	Any member of the class of hydroxybenzoic acids carrying two phenolic hydroxy groups on the benzene ring and its derivatives.
catechols	Any compound containing an o-diphenol component.
[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
Metabolism	1496	1108
Biological oxidations	150	276
Phase II - Conjugation of compounds	73	122
Methylation	13	38
Vanillin and isovanillin metabolism	0	4
Flavan-3-ol metabolic pathway	0	70

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Chain A, 2-oxoglutarate Oxygenase	Homo sapiens (human)	Potency	35.4813	0.1778	14.3909	39.8107	AID2147
phosphopantetheinyl transferase	Bacillus subtilis	Potency	31.6228	0.1413	37.9142	100.0000	AID1490
GLS protein	Homo sapiens (human)	Potency	3.9811	0.3548	7.9355	39.8107	AID624170
GLI family zinc finger 3	Homo sapiens (human)	Potency	30.6067	0.0007	14.5928	83.7951	AID1259369
Microtubule-associated protein tau	Homo sapiens (human)	Potency	2.8184	0.1800	13.5574	39.8107	AID1460
retinoid X nuclear receptor alpha	Homo sapiens (human)	Potency	24.5202	0.0008	17.5051	59.3239	AID1159527
Histone H2A.x	Cricetulus griseus (Chinese hamster)	Potency	112.9350	0.0391	47.5451	146.8240	AID1224845
lysosomal alpha-glucosidase preproprotein	Homo sapiens (human)	Potency	5.0119	0.0366	19.6376	50.1187	AID2100
thyroid hormone receptor beta isoform 2	Rattus norvegicus (Norway rat)	Potency	11.5411	0.0003	23.4451	159.6830	AID743065; AID743067
DNA polymerase beta	Homo sapiens (human)	Potency	25.1189	0.0224	21.0102	89.1251	AID485314
DNA polymerase iota isoform a (long)	Homo sapiens (human)	Potency	79.4328	0.0501	27.0736	89.1251	AID588590
lethal(3)malignant brain tumor-like protein 1 isoform I	Homo sapiens (human)	Potency	39.8107	0.0752	15.2253	39.8107	AID485360
geminin	Homo sapiens (human)	Potency	0.7308	0.0046	11.3741	33.4983	AID624297
Rap guanine nucleotide exchange factor 3	Homo sapiens (human)	Potency	125.8920	6.3096	60.2008	112.2020	AID720707
[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)
M18 aspartyl aminopeptidase	Plasmodium falciparum 3D7	IC50 (µMol)	0.4794	0.3851	13.0782	100.0000	AID2195
Polyphenol oxidase 2	Agaricus bisporus	IC50 (µMol)	100.0000	0.0340	3.9871	10.0000	AID1059453
Carbonic anhydrase 12	Homo sapiens (human)	Ki	4.0900	0.0002	1.1043	9.9000	AID568365
Carbonic anhydrase 1	Homo sapiens (human)	Ki	1.0800	0.0000	1.3726	10.0000	AID568362
Carbonic anhydrase 2	Homo sapiens (human)	Ki	0.4700	0.0000	0.7236	9.9200	AID568363
72 kDa type IV collagenase	Homo sapiens (human)	IC50 (µMol)	137.0000	0.0000	1.2848	10.0000	AID1799773
Matrilysin	Homo sapiens (human)	IC50 (µMol)	137.0000	0.0014	2.0859	10.0000	AID1799773
Prolyl 4-hydroxylase subunit alpha-1	Gallus gallus (chicken)	Ki	5.0000	5.0000	7.6667	9.0000	AID1799825
Carbonic anhydrase 4	Homo sapiens (human)	Ki	2.4500	0.0002	1.9720	9.9200	AID667535
Carbonic anhydrase 6	Homo sapiens (human)	Ki	4.7200	0.0001	1.4710	9.9200	AID607496; AID667536
Carbonic anhydrase 7	Homo sapiens (human)	Ki	7.8700	0.0002	1.3737	9.9000	AID729536
4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT6	Homo sapiens (human)	IC50 (µMol)	137.0000	0.0600	3.8956	8.3000	AID1799773
Anthrax toxin receptor 2	Homo sapiens (human)	IC50 (µMol)	300.0000	0.3000	0.4535	0.6070	AID725981
Xanthine dehydrogenase/oxidase	Bos taurus (cattle)	IC50 (µMol)	5.8000	0.0030	3.1015	9.8000	AID1800197
Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)	IC50 (µMol)	137.0000	0.0600	3.8956	8.3000	AID1799773
CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)	IC50 (µMol)	137.0000	0.0600	3.8956	8.3000	AID1799773
Carbonic anhydrase 9	Homo sapiens (human)	Ki	4.4500	0.0001	0.7874	9.9000	AID568364
Carbonic anhydrase	Dicentrarchus labrax (European seabass)	Ki	3.2100	2.1300	5.5333	9.4100	AID607497
Carbonic anhydrase 14	Homo sapiens (human)	Ki	0.6900	0.0002	1.5099	9.9000	AID729533
[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)
Chain A, Protocatechuate 3,4-dioxygenase alpha chain	Pseudomonas putida	Kd	1,100.0000	1,100.0000	1,100.0000	1,100.0000	AID977611
Chain B, Protocatechuate 3,4-dioxygenase beta chain	Pseudomonas putida	Kd	1,100.0000	1,100.0000	1,100.0000	1,100.0000	AID977611
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
estrous cycle	Carbonic anhydrase 12	Homo sapiens (human)
chloride ion homeostasis	Carbonic anhydrase 12	Homo sapiens (human)
one-carbon metabolic process	Carbonic anhydrase 12	Homo sapiens (human)
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)
one-carbon metabolic process	Carbonic anhydrase 1	Homo sapiens (human)
morphogenesis of an epithelium	Carbonic anhydrase 2	Homo sapiens (human)
positive regulation of synaptic transmission, GABAergic	Carbonic anhydrase 2	Homo sapiens (human)
positive regulation of cellular pH reduction	Carbonic anhydrase 2	Homo sapiens (human)
angiotensin-activated signaling pathway	Carbonic anhydrase 2	Homo sapiens (human)
regulation of monoatomic anion transport	Carbonic anhydrase 2	Homo sapiens (human)
secretion	Carbonic anhydrase 2	Homo sapiens (human)
regulation of intracellular pH	Carbonic anhydrase 2	Homo sapiens (human)
neuron cellular homeostasis	Carbonic anhydrase 2	Homo sapiens (human)
positive regulation of dipeptide transmembrane transport	Carbonic anhydrase 2	Homo sapiens (human)
regulation of chloride transport	Carbonic anhydrase 2	Homo sapiens (human)
carbon dioxide transport	Carbonic anhydrase 2	Homo sapiens (human)
one-carbon metabolic process	Carbonic anhydrase 2	Homo sapiens (human)
aromatic amino acid family biosynthetic process	3-dehydroquinate synthase	Escherichia coli K-12
amino acid biosynthetic process	3-dehydroquinate synthase	Escherichia coli K-12
aromatic amino acid family biosynthetic process	3-dehydroquinate synthase	Escherichia coli K-12
chorismate biosynthetic process	3-dehydroquinate synthase	Escherichia coli K-12
angiogenesis	72 kDa type IV collagenase	Homo sapiens (human)
ovarian follicle development	72 kDa type IV collagenase	Homo sapiens (human)
ovulation from ovarian follicle	72 kDa type IV collagenase	Homo sapiens (human)
luteinization	72 kDa type IV collagenase	Homo sapiens (human)
blood vessel maturation	72 kDa type IV collagenase	Homo sapiens (human)
intramembranous ossification	72 kDa type IV collagenase	Homo sapiens (human)
proteolysis	72 kDa type IV collagenase	Homo sapiens (human)
negative regulation of cell adhesion	72 kDa type IV collagenase	Homo sapiens (human)
heart development	72 kDa type IV collagenase	Homo sapiens (human)
embryo implantation	72 kDa type IV collagenase	Homo sapiens (human)
parturition	72 kDa type IV collagenase	Homo sapiens (human)
response to xenobiotic stimulus	72 kDa type IV collagenase	Homo sapiens (human)
response to mechanical stimulus	72 kDa type IV collagenase	Homo sapiens (human)
peripheral nervous system axon regeneration	72 kDa type IV collagenase	Homo sapiens (human)
response to activity	72 kDa type IV collagenase	Homo sapiens (human)
protein metabolic process	72 kDa type IV collagenase	Homo sapiens (human)
extracellular matrix disassembly	72 kDa type IV collagenase	Homo sapiens (human)
protein catabolic process	72 kDa type IV collagenase	Homo sapiens (human)
positive regulation of cell migration	72 kDa type IV collagenase	Homo sapiens (human)
collagen catabolic process	72 kDa type IV collagenase	Homo sapiens (human)
response to retinoic acid	72 kDa type IV collagenase	Homo sapiens (human)
cellular response to reactive oxygen species	72 kDa type IV collagenase	Homo sapiens (human)
response to nicotine	72 kDa type IV collagenase	Homo sapiens (human)
endodermal cell differentiation	72 kDa type IV collagenase	Homo sapiens (human)
response to hydrogen peroxide	72 kDa type IV collagenase	Homo sapiens (human)
response to estrogen	72 kDa type IV collagenase	Homo sapiens (human)
negative regulation of vasoconstriction	72 kDa type IV collagenase	Homo sapiens (human)
ephrin receptor signaling pathway	72 kDa type IV collagenase	Homo sapiens (human)
macrophage chemotaxis	72 kDa type IV collagenase	Homo sapiens (human)
response to electrical stimulus	72 kDa type IV collagenase	Homo sapiens (human)
response to hyperoxia	72 kDa type IV collagenase	Homo sapiens (human)
face morphogenesis	72 kDa type IV collagenase	Homo sapiens (human)
bone trabecula formation	72 kDa type IV collagenase	Homo sapiens (human)
prostate gland epithelium morphogenesis	72 kDa type IV collagenase	Homo sapiens (human)
cellular response to amino acid stimulus	72 kDa type IV collagenase	Homo sapiens (human)
cellular response to interleukin-1	72 kDa type IV collagenase	Homo sapiens (human)
cellular response to estradiol stimulus	72 kDa type IV collagenase	Homo sapiens (human)
cellular response to UV-A	72 kDa type IV collagenase	Homo sapiens (human)
cellular response to fluid shear stress	72 kDa type IV collagenase	Homo sapiens (human)
positive regulation of oxidative stress-induced neuron intrinsic apoptotic signaling pathway	72 kDa type IV collagenase	Homo sapiens (human)
response to amyloid-beta	72 kDa type IV collagenase	Homo sapiens (human)
positive regulation of vascular associated smooth muscle cell proliferation	72 kDa type IV collagenase	Homo sapiens (human)
extracellular matrix organization	72 kDa type IV collagenase	Homo sapiens (human)
response to hypoxia	72 kDa type IV collagenase	Homo sapiens (human)
tissue remodeling	72 kDa type IV collagenase	Homo sapiens (human)
membrane protein ectodomain proteolysis	Matrilysin	Homo sapiens (human)
membrane protein intracellular domain proteolysis	Matrilysin	Homo sapiens (human)
antibacterial peptide secretion	Matrilysin	Homo sapiens (human)
antibacterial peptide biosynthetic process	Matrilysin	Homo sapiens (human)
proteolysis	Matrilysin	Homo sapiens (human)
response to xenobiotic stimulus	Matrilysin	Homo sapiens (human)
extracellular matrix disassembly	Matrilysin	Homo sapiens (human)
positive regulation of cell migration	Matrilysin	Homo sapiens (human)
collagen catabolic process	Matrilysin	Homo sapiens (human)
regulation of cell population proliferation	Matrilysin	Homo sapiens (human)
defense response to Gram-negative bacterium	Matrilysin	Homo sapiens (human)
defense response to Gram-positive bacterium	Matrilysin	Homo sapiens (human)
extracellular matrix organization	Matrilysin	Homo sapiens (human)
peptidyl-proline hydroxylation to 4-hydroxy-L-proline	Prolyl 4-hydroxylase subunit alpha-1	Gallus gallus (chicken)
bicarbonate transport	Carbonic anhydrase 4	Homo sapiens (human)
one-carbon metabolic process	Carbonic anhydrase 4	Homo sapiens (human)
detection of chemical stimulus involved in sensory perception of bitter taste	Carbonic anhydrase 6	Homo sapiens (human)
one-carbon metabolic process	Carbonic anhydrase 6	Homo sapiens (human)
positive regulation of synaptic transmission, GABAergic	Carbonic anhydrase 7	Homo sapiens (human)
positive regulation of cellular pH reduction	Carbonic anhydrase 7	Homo sapiens (human)
neuron cellular homeostasis	Carbonic anhydrase 7	Homo sapiens (human)
regulation of chloride transport	Carbonic anhydrase 7	Homo sapiens (human)
regulation of intracellular pH	Carbonic anhydrase 7	Homo sapiens (human)
one-carbon metabolic process	Carbonic anhydrase 7	Homo sapiens (human)
protein glycosylation	4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT6	Homo sapiens (human)
protein N-linked glycosylation	4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT6	Homo sapiens (human)
protein O-linked glycosylation	4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT6	Homo sapiens (human)
ceramide metabolic process	4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT6	Homo sapiens (human)
glycosphingolipid biosynthetic process	4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT6	Homo sapiens (human)
oligosaccharide biosynthetic process	4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT6	Homo sapiens (human)
N-glycan fucosylation	4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT6	Homo sapiens (human)
L-fucose catabolic process	4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT6	Homo sapiens (human)
oocyte axis specification	4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT6	Homo sapiens (human)
xanthine catabolic process	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
regulation of type IV hypersensitivity	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
CD4-positive, CD25-positive, alpha-beta regulatory T cell differentiation	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
leukocyte migration involved in immune response	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
leukocyte migration involved in inflammatory response	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
protein glycosylation	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
ceramide metabolic process	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
inflammatory response	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
embryo implantation	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
oligosaccharide biosynthetic process	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
regulation of cell-cell adhesion	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
positive regulation of cell-cell adhesion	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
L-fucose catabolic process	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
positive regulation of cell adhesion	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
regulation of insulin receptor signaling pathway	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
regulation of cell adhesion molecule production	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
T cell migration	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
lymphocyte migration into lymph node	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
positive regulation of neutrophil migration	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
regulation of leukocyte cell-cell adhesion	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
regulation of leukocyte tethering or rolling	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
positive regulation of leukocyte tethering or rolling	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
positive regulation of leukocyte adhesion to vascular endothelial cell	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
regulation of neutrophil extravasation	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
fucosylation	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
memory B cell differentiation	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)
N-acetylneuraminate metabolic process	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)
protein N-linked glycosylation	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)
ganglioside biosynthetic process via lactosylceramide	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)
O-glycan processing	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)
keratan sulfate biosynthetic process	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)
viral protein processing	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)
protein modification process	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)
sialylation	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)
negative regulation of activated CD8-positive, alpha-beta T cell apoptotic process	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)
protein sialylation	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)
protein glycosylation	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)
response to hypoxia	Carbonic anhydrase 9	Homo sapiens (human)
morphogenesis of an epithelium	Carbonic anhydrase 9	Homo sapiens (human)
response to xenobiotic stimulus	Carbonic anhydrase 9	Homo sapiens (human)
response to testosterone	Carbonic anhydrase 9	Homo sapiens (human)
secretion	Carbonic anhydrase 9	Homo sapiens (human)
one-carbon metabolic process	Carbonic anhydrase 9	Homo sapiens (human)
one-carbon metabolic process	Carbonic anhydrase 14	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
zinc ion binding	Carbonic anhydrase 12	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 12	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)
arylesterase activity	Carbonic anhydrase 1	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 1	Homo sapiens (human)
protein binding	Carbonic anhydrase 1	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 1	Homo sapiens (human)
hydro-lyase activity	Carbonic anhydrase 1	Homo sapiens (human)
cyanamide hydratase activity	Carbonic anhydrase 1	Homo sapiens (human)
arylesterase activity	Carbonic anhydrase 2	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 2	Homo sapiens (human)
protein binding	Carbonic anhydrase 2	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 2	Homo sapiens (human)
cyanamide hydratase activity	Carbonic anhydrase 2	Homo sapiens (human)
nucleotide binding	3-dehydroquinate synthase	Escherichia coli K-12
3-dehydroquinate synthase activity	3-dehydroquinate synthase	Escherichia coli K-12
protein binding	3-dehydroquinate synthase	Escherichia coli K-12
zinc ion binding	3-dehydroquinate synthase	Escherichia coli K-12
lyase activity	3-dehydroquinate synthase	Escherichia coli K-12
metal ion binding	3-dehydroquinate synthase	Escherichia coli K-12
NAD+ binding	3-dehydroquinate synthase	Escherichia coli K-12
fibronectin binding	72 kDa type IV collagenase	Homo sapiens (human)
endopeptidase activity	72 kDa type IV collagenase	Homo sapiens (human)
metalloendopeptidase activity	72 kDa type IV collagenase	Homo sapiens (human)
serine-type endopeptidase activity	72 kDa type IV collagenase	Homo sapiens (human)
protein binding	72 kDa type IV collagenase	Homo sapiens (human)
metallopeptidase activity	72 kDa type IV collagenase	Homo sapiens (human)
zinc ion binding	72 kDa type IV collagenase	Homo sapiens (human)
endopeptidase activity	Matrilysin	Homo sapiens (human)
metalloendopeptidase activity	Matrilysin	Homo sapiens (human)
serine-type endopeptidase activity	Matrilysin	Homo sapiens (human)
protein binding	Matrilysin	Homo sapiens (human)
metallopeptidase activity	Matrilysin	Homo sapiens (human)
zinc ion binding	Matrilysin	Homo sapiens (human)
procollagen-proline 4-dioxygenase activity	Prolyl 4-hydroxylase subunit alpha-1	Gallus gallus (chicken)
iron ion binding	Prolyl 4-hydroxylase subunit alpha-1	Gallus gallus (chicken)
L-ascorbic acid binding	Prolyl 4-hydroxylase subunit alpha-1	Gallus gallus (chicken)
protein binding	Carbonic anhydrase 4	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 4	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 4	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 6	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 6	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 7	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 7	Homo sapiens (human)
fucosyltransferase activity	4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT6	Homo sapiens (human)
4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase activity	4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT6	Homo sapiens (human)
alpha-(1->3)-fucosyltransferase activity	4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT6	Homo sapiens (human)
protein binding	Anthrax toxin receptor 2	Homo sapiens (human)
metal ion binding	Anthrax toxin receptor 2	Homo sapiens (human)
transmembrane signaling receptor activity	Anthrax toxin receptor 2	Homo sapiens (human)
xanthine dehydrogenase activity	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
xanthine oxidase activity	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
iron ion binding	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
molybdenum ion binding	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
protein homodimerization activity	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
molybdopterin cofactor binding	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
flavin adenine dinucleotide binding	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
2 iron, 2 sulfur cluster binding	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
FAD binding	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
protein binding	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
fucosyltransferase activity	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase activity	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
alpha-(1->3)-fucosyltransferase activity	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
beta-galactoside (CMP) alpha-2,3-sialyltransferase activity	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)
sialyltransferase activity	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)
beta-D-galactosyl-(1->3)-N-acetyl-beta-D-galactosaminide alpha-2,3- sialyltransferase	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 9	Homo sapiens (human)
protein binding	Carbonic anhydrase 9	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 9	Homo sapiens (human)
molecular function activator activity	Carbonic anhydrase 9	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 14	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 14	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
plasma membrane	Carbonic anhydrase 12	Homo sapiens (human)
membrane	Carbonic anhydrase 12	Homo sapiens (human)
basolateral plasma membrane	Carbonic anhydrase 12	Homo sapiens (human)
apical plasma membrane	Carbonic anhydrase 12	Homo sapiens (human)
plasma membrane	Carbonic anhydrase 12	Homo sapiens (human)
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)
cytosol	Carbonic anhydrase 1	Homo sapiens (human)
extracellular exosome	Carbonic anhydrase 1	Homo sapiens (human)
cytoplasm	Carbonic anhydrase 2	Homo sapiens (human)
cytosol	Carbonic anhydrase 2	Homo sapiens (human)
plasma membrane	Carbonic anhydrase 2	Homo sapiens (human)
myelin sheath	Carbonic anhydrase 2	Homo sapiens (human)
apical part of cell	Carbonic anhydrase 2	Homo sapiens (human)
extracellular exosome	Carbonic anhydrase 2	Homo sapiens (human)
cytoplasm	Carbonic anhydrase 2	Homo sapiens (human)
plasma membrane	Carbonic anhydrase 2	Homo sapiens (human)
apical part of cell	Carbonic anhydrase 2	Homo sapiens (human)
cytoplasm	3-dehydroquinate synthase	Escherichia coli K-12
collagen-containing extracellular matrix	72 kDa type IV collagenase	Homo sapiens (human)
extracellular region	72 kDa type IV collagenase	Homo sapiens (human)
extracellular space	72 kDa type IV collagenase	Homo sapiens (human)
nucleus	72 kDa type IV collagenase	Homo sapiens (human)
mitochondrion	72 kDa type IV collagenase	Homo sapiens (human)
plasma membrane	72 kDa type IV collagenase	Homo sapiens (human)
sarcomere	72 kDa type IV collagenase	Homo sapiens (human)
collagen-containing extracellular matrix	72 kDa type IV collagenase	Homo sapiens (human)
extracellular space	72 kDa type IV collagenase	Homo sapiens (human)
extracellular region	Matrilysin	Homo sapiens (human)
extracellular matrix	Matrilysin	Homo sapiens (human)
extracellular exosome	Matrilysin	Homo sapiens (human)
extracellular space	Matrilysin	Homo sapiens (human)
endoplasmic reticulum lumen	Prolyl 4-hydroxylase subunit alpha-1	Gallus gallus (chicken)
endoplasmic reticulum	Prolyl 4-hydroxylase subunit alpha-1	Gallus gallus (chicken)
basolateral plasma membrane	Carbonic anhydrase 4	Homo sapiens (human)
rough endoplasmic reticulum	Carbonic anhydrase 4	Homo sapiens (human)
endoplasmic reticulum-Golgi intermediate compartment	Carbonic anhydrase 4	Homo sapiens (human)
Golgi apparatus	Carbonic anhydrase 4	Homo sapiens (human)
trans-Golgi network	Carbonic anhydrase 4	Homo sapiens (human)
plasma membrane	Carbonic anhydrase 4	Homo sapiens (human)
external side of plasma membrane	Carbonic anhydrase 4	Homo sapiens (human)
cell surface	Carbonic anhydrase 4	Homo sapiens (human)
membrane	Carbonic anhydrase 4	Homo sapiens (human)
apical plasma membrane	Carbonic anhydrase 4	Homo sapiens (human)
transport vesicle membrane	Carbonic anhydrase 4	Homo sapiens (human)
secretory granule membrane	Carbonic anhydrase 4	Homo sapiens (human)
brush border membrane	Carbonic anhydrase 4	Homo sapiens (human)
perinuclear region of cytoplasm	Carbonic anhydrase 4	Homo sapiens (human)
extracellular exosome	Carbonic anhydrase 4	Homo sapiens (human)
plasma membrane	Carbonic anhydrase 4	Homo sapiens (human)
extracellular region	Carbonic anhydrase 6	Homo sapiens (human)
extracellular space	Carbonic anhydrase 6	Homo sapiens (human)
cytosol	Carbonic anhydrase 6	Homo sapiens (human)
extracellular exosome	Carbonic anhydrase 6	Homo sapiens (human)
extracellular space	Carbonic anhydrase 6	Homo sapiens (human)
cytosol	Carbonic anhydrase 7	Homo sapiens (human)
cytoplasm	Carbonic anhydrase 7	Homo sapiens (human)
Golgi membrane	4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT6	Homo sapiens (human)
extracellular region	4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT6	Homo sapiens (human)
Golgi apparatus	4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT6	Homo sapiens (human)
Golgi cisterna membrane	4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT6	Homo sapiens (human)
extracellular exosome	4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT6	Homo sapiens (human)
methylosome	4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT6	Homo sapiens (human)
extracellular region	Anthrax toxin receptor 2	Homo sapiens (human)
endoplasmic reticulum membrane	Anthrax toxin receptor 2	Homo sapiens (human)
plasma membrane	Anthrax toxin receptor 2	Homo sapiens (human)
endosome membrane	Anthrax toxin receptor 2	Homo sapiens (human)
plasma membrane	Anthrax toxin receptor 2	Homo sapiens (human)
cell surface	Anthrax toxin receptor 2	Homo sapiens (human)
extracellular space	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
peroxisome	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
xanthine dehydrogenase complex	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
Golgi membrane	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
Golgi apparatus	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
trans-Golgi network	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
membrane	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
Golgi cisterna membrane	Alpha-(1,3)-fucosyltransferase 7	Homo sapiens (human)
Golgi membrane	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)
membrane	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)
trans-Golgi network membrane	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)
extracellular exosome	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)
Golgi medial cisterna membrane	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)
Golgi trans cisterna membrane	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)
membrane	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Homo sapiens (human)
nucleolus	Carbonic anhydrase 9	Homo sapiens (human)
plasma membrane	Carbonic anhydrase 9	Homo sapiens (human)
membrane	Carbonic anhydrase 9	Homo sapiens (human)
basolateral plasma membrane	Carbonic anhydrase 9	Homo sapiens (human)
microvillus membrane	Carbonic anhydrase 9	Homo sapiens (human)
plasma membrane	Carbonic anhydrase 9	Homo sapiens (human)
plasma membrane	Carbonic anhydrase 14	Homo sapiens (human)
membrane	Carbonic anhydrase 14	Homo sapiens (human)
basolateral plasma membrane	Carbonic anhydrase 14	Homo sapiens (human)
apical plasma membrane	Carbonic anhydrase 14	Homo sapiens (human)
plasma membrane	Carbonic anhydrase 14	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (236)

Assay ID	Title	Year	Journal	Article
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.
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.
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.
AID651635	Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1745845	Primary qHTS for Inhibitors of ATXN expression
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.
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.
AID1082339	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 2% under dark conditions measured 5 to 60 min post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID425005	DPPH radical scavenging activity assessed as ratio of antioxidant concentration to drug level causing 50% decrease in DPPH level at steady state at 100 ug by TLC autographic assay	2009	Journal of natural products, May-22, Volume: 72, Issue:5	Antioxidant phenylethanoid glycosides and a neolignan from Jacaranda caucana.
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.
AID338329	Antiplatelet activity against rat platelet rich plasma assessed as inhibition of ADP-induced platelet aggregation pretreated 2 mins before ADP challenge
AID1272397	Aqueous solubility of the compound	2016	Bioorganic & medicinal chemistry, Feb-15, Volume: 24, Issue:4	Identification of B. anthracis N(5)-carboxyaminoimidazole ribonucleotide mutase (PurE) active site binding compounds via fragment library screening.
AID549271	Antioxidant activity in mouse brain assessed as inhibition of Fe2+/ascorbate-induced lipid peroxidation up to 20 ug/ml by TBARS assay relative to control	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano).
AID1272395	Binding affinity to Bacillus anthracis PurE by Surface Plasmon Resonance analysis	2016	Bioorganic & medicinal chemistry, Feb-15, Volume: 24, Issue:4	Identification of B. anthracis N(5)-carboxyaminoimidazole ribonucleotide mutase (PurE) active site binding compounds via fragment library screening.
AID549261	Antioxidant activity assessed as DPPH radical scavenging activity at 5 ug/ml after 30 mins	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano).
AID1313263	Inhibition of chymotrypsin like activity of 20S proteasome (unknown origin) using suc-leu-leu-val-tyr-AMC as substrate at 10 uM after 40 mins in presence of zinc by fluorescence assay	2016	Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15	Cupriphilic compounds to aid in proteasome inhibition.
AID375992	Inhibition of HIV1 recombinant integrase expressed in Escherichia coli	2006	Journal of natural products, Apr, Volume: 69, Issue:4	Vanillic acid glycoside and quinic acid derivatives from Gardeniae Fructus.
AID642414	Estrogenic activity at ERalpha in human MVLN cells at 100 ug/mL after 24 hrs by luciferase reporter gene assay relative to E2	2012	Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1	Discovery of estrogen receptor α modulators from natural compounds in Si-Wu-Tang series decoctions using estrogen-responsive MCF-7 breast cancer cells.
AID1082345	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 2% under light conditions measured 5 to 60 min post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID642415	Estrogenic activity at ERalpha in human MVLN cells at 20 ug/mL after 24 hrs by luciferase reporter gene assay relative to E2	2012	Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1	Discovery of estrogen receptor α modulators from natural compounds in Si-Wu-Tang series decoctions using estrogen-responsive MCF-7 breast cancer cells.
AID1101855	Antifungal activity against Saccharomyces cerevisiae ATCC 7754 after 48 hr by microdilution method	2002	Journal of agricultural and food chemistry, Jul-03, Volume: 50, Issue:14	Molecular design of antifungal agents.
AID1059454	Antioxidant activity assessed as trolox equivalent of APPH-induced peroxyl radical scavenging activity at 5 to 20 uM measured every 1 min for 120 mins by ORAC fluorescence assay	2013	Bioorganic & medicinal chemistry letters, Dec-15, Volume: 23, Issue:24	Synthesis, antioxidant capacity, and structure-activity relationships of tri-O-methylnorbergenin analogues on tyrosinase inhibition.
AID546248	Antimelanogenic activity in mouse B16 cells assessed as decrease in tyrosinase expression at 20 ug/ml after 72 hrs by flow cytometry assay	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano).
AID1082324	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 1% under dark conditions measured 48 hr post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID761681	Antibacterial activity against Aspergillus flavus IMI 052104 at 50 ug/ml after 24 hrs by agar well diffusion method relative to control	2013	European journal of medicinal chemistry, Aug, Volume: 66	A novel one-pot synthesis and preliminary biological activity evaluation of cis-restricted polyhydroxy stilbenes incorporating protocatechuic acid and cinnamic acid fragments.
AID549276	Cytotoxicity against human HS68 cells up to 100 ug/ml after 72 hrs by MTT assay	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano).
AID546251	Antimelanogenic activity in mouse B16 cells assessed as decrease in TRP2 expression at 20 ug/ml after 72 hrs by Western blotting	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano).
AID566702	Inhibition of human recombinant MMP1 at 1 mM after 30 mins	2011	Journal of medicinal chemistry, Jan-27, Volume: 54, Issue:2	Identifying chelators for metalloprotein inhibitors using a fragment-based approach.
AID761689	Antioxidant activity assessed as DPPH free radical scavenging activity at 3.3 uM measured every 10 mins	2013	European journal of medicinal chemistry, Aug, Volume: 66	A novel one-pot synthesis and preliminary biological activity evaluation of cis-restricted polyhydroxy stilbenes incorporating protocatechuic acid and cinnamic acid fragments.
AID1313259	Inhibition of chymotrypsin like activity of 20S proteasome (unknown origin) using suc-leu-leu-val-tyr-AMC as substrate at 10 uM after 40 mins in presence of 1 uM copper by fluorescence assay	2016	Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15	Cupriphilic compounds to aid in proteasome inhibition.
AID293934	Inhibition of pieris rapae Phenoloxidase	2007	Bioorganic & medicinal chemistry, Mar-01, Volume: 15, Issue:5	3D-QSAR and molecular docking studies of benzaldehyde thiosemicarbazone, benzaldehyde, benzoic acid, and their derivatives as phenoloxidase inhibitors.
AID375989	Antioxidant activity assessed as superoxide anion scavenging activity by xanthine oxidase oxidation system relative to control	2006	Journal of natural products, Apr, Volume: 69, Issue:4	Vanillic acid glycoside and quinic acid derivatives from Gardeniae Fructus.
AID1417094	Inhibition of recombinant oligo-histidine-tagged Leishmania major DHODH expressed in Escherichia coli BL21(DE3) cells using DHO as substrate measured after 60 secs	2018	European journal of medicinal chemistry, Sep-05, Volume: 157	Natural products as inhibitors of Leishmania major dihydroorotate dehydrogenase.
AID568364	Inhibition of human carbonic anhydrase 9 preincubated for 15 mins by CO2 hydration stopped-flow assay	2011	Bioorganic & medicinal chemistry, Feb-15, Volume: 19, Issue:4	Kinetic and docking studies of phenol-based inhibitors of carbonic anhydrase isoforms I, II, IX and XII evidence a new binding mode within the enzyme active site.
AID55747	Dissociation constant against 1A dihydroate dehydrogenase (1A DHOD) from Lactococcus lactis at 25 degrees C pH 8.0	2001	Journal of medicinal chemistry, Aug-30, Volume: 44, Issue:18	Specific inhibition of a family 1A dihydroorotate dehydrogenase by benzoate pyrimidine analogues.
AID1082348	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 0.25% under dark conditions measured 48 hr post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID761678	Inhibition of mushroom tyrosinase using L-tyrosine as substrate at 23 uM after 30 mins by spectrophotometric analysis	2013	European journal of medicinal chemistry, Aug, Volume: 66	A novel one-pot synthesis and preliminary biological activity evaluation of cis-restricted polyhydroxy stilbenes incorporating protocatechuic acid and cinnamic acid fragments.
AID397160	Antioxidant activity against AAPH-induced lipid peroxidation in human plasma LDL at 0.01 to 0.1 umol/L preincubated for 1 hr before AAPH challenge	2001	Journal of natural products, Apr, Volume: 64, Issue:4	Specific antioxidant activity of caffeoyl derivatives and other natural phenolic compounds: LDL protection against oxidation and decrease in the proinflammatory lysophosphatidylcholine production.
AID1675091	Binding affinity to wild type rat DNA polymerase beta assessed as inhibition of dRP excision in presence of 32P-end labelled duplex DNA at 50 uM by SDS PAGE analysis	2020	Bioorganic & medicinal chemistry, 09-01, Volume: 28, Issue:17	An assay for DNA polymerase β lyase inhibitors that engage the catalytic nucleophile for binding.
AID276460	DPPH radical scavenging activity	2006	Bioorganic & medicinal chemistry letters, Nov-15, Volume: 16, Issue:22	Synthesis and free radical scavenging activity of a novel metabolite from the fungus Colletotrichum gloeosporioides.
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
AID549282	Antimelanogenic activity in mouse B16 cells assessed as decrease in MC1R expression at 20 ug/ml after 72 hrs by Western blotting	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano).
AID280296	Inhibition of attachment of HL60 cells to P-selectin at 109 uM after 5 mins	2007	Journal of medicinal chemistry, Mar-22, Volume: 50, Issue:6	Rational design of novel, potent small molecule pan-selectin antagonists.
AID566706	Inhibition of human recombinant MMP9 at 1 mM after 30 mins	2011	Journal of medicinal chemistry, Jan-27, Volume: 54, Issue:2	Identifying chelators for metalloprotein inhibitors using a fragment-based approach.
AID1675087	Binding affinity to human DNA polymerase beta with methyl-lysine modification at 72 assessed as inhibition of dRP excision in presence of 32P-end labelled duplex DNA at 25 uM by SDS PAGE	2020	Bioorganic & medicinal chemistry, 09-01, Volume: 28, Issue:17	An assay for DNA polymerase β lyase inhibitors that engage the catalytic nucleophile for binding.
AID1102544	Inhibition of tyrosinase activity in Oryza sativa Indica (rice) bran using L-tyrosine as substrate at 0.5 umol/ml after 60 min by spectrophotometric analysis	2003	Journal of agricultural and food chemistry, Nov-19, Volume: 51, Issue:24	Tyrosinase inhibitor from black rice bran.
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).
AID549286	Antimelanogenic activity in mouse B16 cells assessed as decrease in MITF expression at 20 ug/ml after 72 hrs by flow cytometry assay	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano).
AID3250	Inhibition constant for binding to Zn2+ form of 3-dehydroquinate synthase (DHQ) purified from Escherichia coli	2001	Bioorganic & medicinal chemistry letters, Jun-18, Volume: 11, Issue:12	Aromatic inhibitors of dehydroquinate synthase: synthesis, evaluation and implications for gallic acid biosynthesis.
AID1082342	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 0.25% under light conditions measured 5 to 60 min post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID1082358	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 0.25% under light conditions measured 24 hr post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID1239713	Anti-platelet activity in rat platelet rich plasma assessed as inhibition of ADP and calcium-induced platelet aggregation at 100 uM pre-incubated at 37 degC for 10 mins and measured 30 mins after ADP and calcium addition	2015	Bioorganic & medicinal chemistry letters, Aug-15, Volume: 25, Issue:16	Potential therapeutic agents for circulatory diseases from Bauhinia glauca Benth.subsp. pernervosa. (Da Ye Guan Men).
AID338336	Antiplatelet activity against rat platelet rich plasma assessed as inhibition of collagen-induced platelet aggregation at 0.25 mg/ml pretreated 2 mins before collagen challenge
AID549262	Antioxidant activity assessed as DPPH radical scavenging activity at 10 ug/ml after 30 mins	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano).
AID1244909	Cytotoxicity against human SW480 cells after 48 hrs by MTT assay	2015	European journal of medicinal chemistry, Sep-18, Volume: 102	Antitumor activity of endoperoxide-iron chelator conjugates-design, synthesis and biological evaluation.
AID758940	Agonist activity at human LXRalpha-LBD assessed as recruitment of co-activator peptide after 2 hrs by TR-FRET assay	2013	Bioorganic & medicinal chemistry letters, Jul-15, Volume: 23, Issue:14	Cyanidin, a natural flavonoid, is an agonistic ligand for liver X receptor alpha and beta and reduces cellular lipid accumulation in macrophages and hepatocytes.
AID311580	Antioxidant activity assessed as DPPH radical scavenging activity	2007	Journal of natural products, Oct, Volume: 70, Issue:10	Structures and radical-scavenging activities of phenolic constituents from the bark of Picea jezoensis var. jezoensis.
AID338330	Antiplatelet activity against rat platelet rich plasma assessed as inhibition of arachidonic acid-induced platelet aggregation pretreated 2 mins before arachidonic acid challenge
AID1424230	Electrochemical behaviour of the compound assessed as peak potential using disposable screen-printed carbon electrodes	2017	European journal of medicinal chemistry, Jun-16, Volume: 133	Free radicals and polyphenols: The redox chemistry of neurodegenerative diseases.
AID1313262	Inhibition of chymotrypsin like activity of 20S proteasome (unknown origin) using suc-leu-leu-val-tyr-AMC as substrate at 10 uM after 40 mins in presence of iron by fluorescence assay	2016	Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15	Cupriphilic compounds to aid in proteasome inhibition.
AID492404	Binding affinity to human serum albumin in 100 mM phosphate buffer at pH 7.4 assessed as formation of biotin-LC-hydrazide labeled protein carbonyls at 100 uM pretreated 60 mins before biotin-LC-hydrazide challenge measured after 60 mins by SDS-PAGE/Wester	2010	Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14	Structural characteristics of green tea catechins for formation of protein carbonyl in human serum albumin.
AID375991	Antioxidant activity assessed as inhibition of 2,2'-azobis(2-amidinopropane)dihydrochloride-induced lipid peroxidation at 3.125 ug/ml by ferric thiocyanate system relative to control	2006	Journal of natural products, Apr, Volume: 69, Issue:4	Vanillic acid glycoside and quinic acid derivatives from Gardeniae Fructus.
AID761680	Antibacterial activity against Fusarium graminearum ATCC 24373 at 50 ug/ml after 24 hrs by agar well diffusion method relative to control	2013	European journal of medicinal chemistry, Aug, Volume: 66	A novel one-pot synthesis and preliminary biological activity evaluation of cis-restricted polyhydroxy stilbenes incorporating protocatechuic acid and cinnamic acid fragments.
AID614100	Antimicrobial activity against Staphylococcus aureus ATCC 9144 after 24 hrs using thiazoyl blue by agar overlay bioautography method	2011	Bioorganic & medicinal chemistry, Sep-01, Volume: 19, Issue:17	Tylosema esculentum extractives and their bioactivity.
AID1082338	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 1% under dark conditions measured 5 to 60 min post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID400524	Antioxidant activity assessed as DPPH radical scavenging activity at 0.1 mg/mL	2004	Journal of natural products, Mar, Volume: 67, Issue:3	Antityrosinase principles and constituents of the petals of Crocus sativus.
AID338333	Antiplatelet activity against rat platelet rich plasma assessed as inhibition of arachidonic acid-induced platelet aggregation at 0.5 mg/ml pretreated 2 mins before arachidonic acid challenge
AID667535	Inhibition of human CA4 using 4NPA as substrate for 3 mins by Lineweaver burk plot analysis	2012	European journal of medicinal chemistry, Aug, Volume: 54	Synthesis and carbonic anhydrase inhibitory properties of novel bromophenols and their derivatives including natural products: vidalol B.
AID1675088	Binding affinity to wild type human DNA polymerase beta assessed as inhibition of dRP excision in presence of 32P-end labelled duplex DNA at 25 uM by SDS PAGE analysis	2020	Bioorganic & medicinal chemistry, 09-01, Volume: 28, Issue:17	An assay for DNA polymerase β lyase inhibitors that engage the catalytic nucleophile for binding.
AID1592383	Antioxidant activity assessed as DPPH radical scavenging activity measured after 45 mins by UV-Visible spectrophotometric based assay
AID55746	Inhibitory activity against family of dihydroorotate dehydrogenase 1A (1A DHOD) from Lactococcus lactis at 1 uMolar concentration	2001	Journal of medicinal chemistry, Aug-30, Volume: 44, Issue:18	Specific inhibition of a family 1A dihydroorotate dehydrogenase by benzoate pyrimidine analogues.
AID1244907	Cytotoxicity against human HL60 cells after 48 hrs by MTT assay	2015	European journal of medicinal chemistry, Sep-18, Volume: 102	Antitumor activity of endoperoxide-iron chelator conjugates-design, synthesis and biological evaluation.
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.
AID549281	Antimelanogenic activity in mouse B16 cells assessed as decrease in MCIR expression at 20 ug/ml after 72 hrs by flow cytometry assay	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano).
AID1449738	Inhibition of Malassezia globosa recombinant beta-carbonic anhydrase preincubated for 15 mins prior to testing measured for 10 to 100 secs by phenol red-based stopped-flow CO2 hydration assay	2017	Bioorganic & medicinal chemistry, 05-01, Volume: 25, Issue:9	Inhibition of Malassezia globosa carbonic anhydrase with phenols.
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.
AID761683	Antibacterial activity against Candida albicans ATCC 10231 at 50 ug/ml after 24 hrs by agar well diffusion method relative to nystatine	2013	European journal of medicinal chemistry, Aug, Volume: 66	A novel one-pot synthesis and preliminary biological activity evaluation of cis-restricted polyhydroxy stilbenes incorporating protocatechuic acid and cinnamic acid fragments.
AID1272394	Binding affinity to Bacillus anthracis PurE assessed as decrease in signal by STD-NMR analysis in presence of CAIR	2016	Bioorganic & medicinal chemistry, Feb-15, Volume: 24, Issue:4	Identification of B. anthracis N(5)-carboxyaminoimidazole ribonucleotide mutase (PurE) active site binding compounds via fragment library screening.
AID276003	Superoxide anion radical scavenging activity by xanthine/xanthine oxidase method	2006	Bioorganic & medicinal chemistry letters, Nov-01, Volume: 16, Issue:21	Free radical scavengers from the medicinal mushroom Inonotus xeranticus and their proposed biogenesis.
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.
AID1449688	Cytotoxicity against HEK293 cells harboring pendrin P123S mutant after 72 hrs by MTT assay	2017	Bioorganic & medicinal chemistry, 05-01, Volume: 25, Issue:9	Discovery of (2-aminophenyl)methanol as a new molecular chaperone that rescues the localization of P123S mutant pendrin stably expressed in HEK293 cells.
AID1449741	Selectivity ratio of Ki for recombinant human carbonic anhydrase 1 to Ki for recombinant Malassezia globosa beta-carbonic anhydrase	2017	Bioorganic & medicinal chemistry, 05-01, Volume: 25, Issue:9	Inhibition of Malassezia globosa carbonic anhydrase with phenols.
AID1082341	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 0.125% under light conditions measured 5 to 60 min post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID1371026	Inhibition of Saccharomyces cerevisiae alpha-glucosidase using p-nitrophenyl-alpha-D-glucopyranoside substrate incubated for 30 mins	2017	Journal of natural products, 04-28, Volume: 80, Issue:4	α-Glucosidase Inhibitory and Cytotoxic Taxane Diterpenoids from the Stem Bark of Taxus wallichiana.
AID1059453	Inhibition of mushroom tyrosinase using L-tyrosine as substrate preincubated for 10 mins followed by enzyme addition measured after 20 mins by microplate reader analysis	2013	Bioorganic & medicinal chemistry letters, Dec-15, Volume: 23, Issue:24	Synthesis, antioxidant capacity, and structure-activity relationships of tri-O-methylnorbergenin analogues on tyrosinase inhibition.
AID546249	Antimelanogenic activity in mouse B16 cells assessed as decrease in TRP1 expression at 20 ug/ml after 72 hrs by flow cytometry assay	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano).
AID276002	ABTS radical scavenging activity	2006	Bioorganic & medicinal chemistry letters, Nov-01, Volume: 16, Issue:21	Free radical scavengers from the medicinal mushroom Inonotus xeranticus and their proposed biogenesis.
AID611697	Inhibition of Escherichia coli beta-glucuronidase assessed as inhibition of p-nitrophenyl-beta-D-glucuronide hydrolysis preincubated for 30 mins measured 30 mins after substrate addition by spectrophotometry	2011	Journal of natural products, Jun-24, Volume: 74, Issue:6	Isoflavone dimers and other bioactive constituents from the figs of Ficus mucuso.
AID761682	Antibacterial activity against Aspergillus niger A3 at 50 ug/ml after 24 hrs by agar well diffusion method relative to control	2013	European journal of medicinal chemistry, Aug, Volume: 66	A novel one-pot synthesis and preliminary biological activity evaluation of cis-restricted polyhydroxy stilbenes incorporating protocatechuic acid and cinnamic acid fragments.
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).
AID758943	Binding affinity to human LXRalpha-LBD by surface plasmon resonance	2013	Bioorganic & medicinal chemistry letters, Jul-15, Volume: 23, Issue:14	Cyanidin, a natural flavonoid, is an agonistic ligand for liver X receptor alpha and beta and reduces cellular lipid accumulation in macrophages and hepatocytes.
AID1102543	Inhibition of tyrosinase activity in Oryza sativa Indica (rice) bran using L-tyrosine as substrate after 60 min by spectrophotometric analysis	2003	Journal of agricultural and food chemistry, Nov-19, Volume: 51, Issue:24	Tyrosinase inhibitor from black rice bran.
AID549265	Antioxidant activity assessed as DPPH radical scavenging activity after 30 mins	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano).
AID397159	Antioxidant activity against Cu2+-induced lipid peroxidation in human plasma LDL at 0.01 to 0.1 umol/L preincubated for 1 hr before Cu2+ challenge	2001	Journal of natural products, Apr, Volume: 64, Issue:4	Specific antioxidant activity of caffeoyl derivatives and other natural phenolic compounds: LDL protection against oxidation and decrease in the proinflammatory lysophosphatidylcholine production.
AID549278	Inhibition of DOPA oxidase activity of tyrosinase in mouse B16 cells at 10 to 20 ug/ml after 72 hrs by colorimetry	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano).
AID549284	Antioxidant activity in mouse BNL-CL2 cells assessed as inhibition of H2O2-induced ROS production by DCFHDA assay relative to alpha-tochopherol	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano).
AID1244908	Cytotoxicity against human A549 cells after 48 hrs by MTT assay	2015	European journal of medicinal chemistry, Sep-18, Volume: 102	Antitumor activity of endoperoxide-iron chelator conjugates-design, synthesis and biological evaluation.
AID3249	Inhibition constant for binding to Co2+ form of 3-dehydroquinate synthase (DHQ) purified from Escherichia coli	2001	Bioorganic & medicinal chemistry letters, Jun-18, Volume: 11, Issue:12	Aromatic inhibitors of dehydroquinate synthase: synthesis, evaluation and implications for gallic acid biosynthesis.
AID55861	Inhibition constant against 1A dihydroate dehydrogenase (1A DHOD) from Lactococcus lactis	2001	Journal of medicinal chemistry, Aug-30, Volume: 44, Issue:18	Specific inhibition of a family 1A dihydroorotate dehydrogenase by benzoate pyrimidine analogues.
AID549279	Antimelanogenic activity in mouse B16 cells assessed as inhibition of alpha-MSH-induced melanin formation after 72 hrs by spectrophotometry	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano).
AID338339	Antiplatelet activity against rat platelet rich plasma assessed as inhibition of ADP-induced platelet aggregation at 1 mg/ml pretreated 2 mins before ADP challenge
AID549275	Cytotoxicity against mouse B16 cells up to 100 ug/ml after 72 hrs by MTT assay	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano).
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.
AID280295	Inhibition of attachment of HL60 cells to E-selectin at 109 uM after 5 mins	2007	Journal of medicinal chemistry, Mar-22, Volume: 50, Issue:6	Rational design of novel, potent small molecule pan-selectin antagonists.
AID280294	Inhibition of human L-selectin after 2 hrs at 100 uM	2007	Journal of medicinal chemistry, Mar-22, Volume: 50, Issue:6	Rational design of novel, potent small molecule pan-selectin antagonists.
AID1698073	Neuroprotective activity against glutamate-induced cell death in mouse HT-22 cells assessed as increase in cell viability after 24 hrs by EZ-Cytox assay
AID388742	Inhibition of cataracted human eye lens aldose reductase	2008	Bioorganic & medicinal chemistry, Dec-01, Volume: 16, Issue:23	Inhibition of aldose reductase from cataracted eye lenses by finger millet (Eleusine coracana) polyphenols.
AID1082349	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 0.125% under dark conditions measured 24 hr post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID425006	Antioxidant activity assessed as protection against peroxyl radical-induced alkaline phosphatase activity loss by microplate assay	2009	Journal of natural products, May-22, Volume: 72, Issue:5	Antioxidant phenylethanoid glycosides and a neolignan from Jacaranda caucana.
AID667536	Inhibition of human CA6 using 4NPA as substrate for 3 mins by Lineweaver burk plot analysis	2012	European journal of medicinal chemistry, Aug, Volume: 54	Synthesis and carbonic anhydrase inhibitory properties of novel bromophenols and their derivatives including natural products: vidalol B.
AID1082359	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 0.5% under light conditions measured 24 hr post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID1449689	Cytotoxicity against HEK293 cells harboring pendrin P123S mutant assessed as decrease in cell viability at 15 mM after 72 hrs by MTT assay	2017	Bioorganic & medicinal chemistry, 05-01, Volume: 25, Issue:9	Discovery of (2-aminophenyl)methanol as a new molecular chaperone that rescues the localization of P123S mutant pendrin stably expressed in HEK293 cells.
AID1082355	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 0.125% under light conditions measured 48 hr post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID1453183	Binding affinity to CK2alpha (unknown origin) assessed as change in melting temperature by thermal shift assay	2017	Bioorganic & medicinal chemistry, 07-01, Volume: 25, Issue:13	A fragment-based approach leading to the discovery of a novel binding site and the selective CK2 inhibitor CAM4066.
AID1082347	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 0.125% under dark conditions measured 48 hr post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID280292	Inhibition of human P-selectin after 2 hrs at 100 uM	2007	Journal of medicinal chemistry, Mar-22, Volume: 50, Issue:6	Rational design of novel, potent small molecule pan-selectin antagonists.
AID647813	Antifilarial activity against microfilariae Brugia malayi assessed as inhibition of motility at 31.25 ug/ml incubated for 48 hrs followed by washout measured after 1 hr in the absence of drug by microscopic analysis	2012	European journal of medicinal chemistry, Apr, Volume: 50	Galactolipids from Bauhinia racemosa as a new class of antifilarial agents against human lymphatic filarial parasite, Brugia malayi.
AID1082356	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 0.25% under light conditions measured 48 hr post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID1592384	Antioxidant activity assessed as ABTS radical scavenging activity measured after 15 mins by UV-Visible spectrophotometric based assay
AID647625	Antioxidant activity assessed as trolox equivalent of ABTS radical scavenging activity relative to control	2012	European journal of medicinal chemistry, Apr, Volume: 50	New losartan-hydrocaffeic acid hybrids as antihypertensive-antioxidant dual drugs: Ester, amide and amine linkers.
AID450612	Antitumor initiating activity in human Chang cells assessed as ratio of inhibition of cellular transformation in presence of NOR1 to compound and NOR1 at 350 nmol treated 1 min before NOR1 addition measured after 1 hr by light microscopy	2009	Bioorganic & medicinal chemistry, Sep-01, Volume: 17, Issue:17	Anti-tumor-initiating effects of phenolic compounds isolated from the bark of Picea jezoensis var. jezoensis.
AID647808	Antifilarial activity against adult Brugia malayi assessed as inhibition of motility at 31.25 ug/ml incubated for 48 hrs followed by washout measured after 1 hr in the absence of drug by microscopic analysis	2012	European journal of medicinal chemistry, Apr, Volume: 50	Galactolipids from Bauhinia racemosa as a new class of antifilarial agents against human lymphatic filarial parasite, Brugia malayi.
AID1244910	Cytotoxicity against human SMMC7721 cells after 48 hrs by MTT assay	2015	European journal of medicinal chemistry, Sep-18, Volume: 102	Antitumor activity of endoperoxide-iron chelator conjugates-design, synthesis and biological evaluation.
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
AID549269	Antioxidant activity assessed as inhibition of Fe2+/ascorbate-induced lipid peroxidation by TBA assay	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano).
AID549268	Antioxidant activity assessed as ferrous ion chelating effect after 10 mins	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano).
AID549263	Antioxidant activity assessed as DPPH radical scavenging activity at 20 ug/ml after 30 mins	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano).
AID546252	Antimelanogenic activity in mouse B16 cells assessed as decrease in TRP1 expression at 20 ug/ml after 72 hrs by Western blotting	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano).
AID1542227	Inhibition of synthetic AcPHF6 peptide aggregation in pH 7.4 phosphate buffer assessed as reduction in fluorescence intensity at 50 uM and measured every minute over 2 hrs with 5 secs shaking prior to each reading by ThT fluorescence assay	2019	European journal of medicinal chemistry, Apr-01, Volume: 167	Repurposing nitrocatechols: 5-Nitro-α-cyanocarboxamide derivatives of caffeic acid and caffeic acid phenethyl ester effectively inhibit aggregation of tau-derived hexapeptide AcPHF6.
AID1082343	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 0.5% under light conditions measured 5 to 60 min post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID462333	Inhibition of theophylline-stimulated melanogenesis in mouse B16-4A5 cells at 30 uM after 72 hrs	2010	Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6	Melanogenesis inhibitors from the desert plant Anastatica hierochuntica in B16 melanoma cells.
AID276004	DPPH radical scavenging activity	2006	Bioorganic & medicinal chemistry letters, Nov-01, Volume: 16, Issue:21	Free radical scavengers from the medicinal mushroom Inonotus xeranticus and their proposed biogenesis.
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.
AID403754	Antitubercular activity against Mycobacterium tuberculosis 90-221387	2005	Journal of natural products, Sep, Volume: 68, Issue:9	Antitubercular constituents from the stem wood of Cinnamomum kotoense.
AID758939	Agonist activity at human LXRbeta-LBD assessed as recruitment of co-activator peptide after 2 hrs by TR-FRET assay	2013	Bioorganic & medicinal chemistry letters, Jul-15, Volume: 23, Issue:14	Cyanidin, a natural flavonoid, is an agonistic ligand for liver X receptor alpha and beta and reduces cellular lipid accumulation in macrophages and hepatocytes.
AID1248399	Inhibition of alpha-amylase (unknown origin) relative to control	2015	Bioorganic & medicinal chemistry, Oct-15, Volume: 23, Issue:20	From carbohydrates to drug-like fragments: Rational development of novel α-amylase inhibitors.
AID311581	Antioxidant activity assessed as superoxide anion radical scavenging activity	2007	Journal of natural products, Oct, Volume: 70, Issue:10	Structures and radical-scavenging activities of phenolic constituents from the bark of Picea jezoensis var. jezoensis.
AID1244912	Selectivity ratio of IC50 for human HL7702 cells to IC50 for human SMMC7721 cells	2015	European journal of medicinal chemistry, Sep-18, Volume: 102	Antitumor activity of endoperoxide-iron chelator conjugates-design, synthesis and biological evaluation.
AID462342	Toxicity in mouse B16-4A5 cells assessed as inhibition of cell proliferation at 30 uM in presence of 1 mM theophylline after 72 hrs by WST8 dye reduction assay	2010	Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6	Melanogenesis inhibitors from the desert plant Anastatica hierochuntica in B16 melanoma cells.
AID568362	Inhibition of human carbonic anhydrase 1 preincubated for 15 mins by CO2 hydration stopped-flow assay	2011	Bioorganic & medicinal chemistry, Feb-15, Volume: 19, Issue:4	Kinetic and docking studies of phenol-based inhibitors of carbonic anhydrase isoforms I, II, IX and XII evidence a new binding mode within the enzyme active site.
AID1675086	Binding affinity to human DNA polymerase beta with homo-lysine modification at 72 assessed as inhibition of dRP excision in presence of 32P-end labelled duplex DNA at 25 uM by SDS PAGE	2020	Bioorganic & medicinal chemistry, 09-01, Volume: 28, Issue:17	An assay for DNA polymerase β lyase inhibitors that engage the catalytic nucleophile for binding.
AID549272	Antioxidant activity in mouse liver assessed as inhibition of Fe2+/ascorbate-induced lipid peroxidation up to 100 ug/ml by TBARS assay relative to control	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano).
AID1592386	Electrochemical behavior of the compound assessed as redox potential corrected toward saturated Ag/AgCl reference electrode by differential pulse voltammetry
AID568363	Inhibition of human carbonic anhydrase 2 preincubated for 15 mins by CO2 hydration stopped-flow assay	2011	Bioorganic & medicinal chemistry, Feb-15, Volume: 19, Issue:4	Kinetic and docking studies of phenol-based inhibitors of carbonic anhydrase isoforms I, II, IX and XII evidence a new binding mode within the enzyme active site.
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.
AID549260	Antioxidant activity assessed as DPPH radical scavenging activity at 1 ug/ml after 30 mins	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano).
AID607496	Inhibition of human CA6 using 4-nitrophenylacetate substrate by esterase assay	2011	Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14	In vitro inhibition of α-carbonic anhydrase isozymes by some phenolic compounds.
AID397156	Antioxidant activity against Cu2+-induced lipid peroxidation in human plasma LDL at 1 umol/L preincubated for 1 hr before Cu2+ challenge	2001	Journal of natural products, Apr, Volume: 64, Issue:4	Specific antioxidant activity of caffeoyl derivatives and other natural phenolic compounds: LDL protection against oxidation and decrease in the proinflammatory lysophosphatidylcholine production.
AID549264	Antioxidant activity assessed as DPPH radical scavenging activity at 100 ug/ml after 30 mins	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano).
AID1424229	Electrochemical behaviour of the compound assessed as peak potential	2017	European journal of medicinal chemistry, Jun-16, Volume: 133	Free radicals and polyphenols: The redox chemistry of neurodegenerative diseases.
AID1082352	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 1% under dark conditions measured 24 hr post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID1449696	Chaperone activity at recombinant human C-terminal FLAG-tagged pendrin P123S mutant expressed in HEK293 cells assessed as increase in localization of protein mutant in plasma membrane at 1 to 30 mM after 12 hrs by DAPI staining based immunofluorescence mi	2017	Bioorganic & medicinal chemistry, 05-01, Volume: 25, Issue:9	Discovery of (2-aminophenyl)methanol as a new molecular chaperone that rescues the localization of P123S mutant pendrin stably expressed in HEK293 cells.
AID1082346	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 5% under light conditions measured 5 to 60 min post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID549283	Antimelanogenic activity in mouse B16 cells assessed as decrease in MITF expression at 20 ug/ml after 72 hrs by Western blotting	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano).
AID1082336	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 0.25% under dark conditions measured 5 to 60 min post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID1059449	Inhibition of mushroom tyrosinase using L-tyrosine as substrate at 100 uM preincubated for 10 mins followed by enzyme addition measured after 20 mins by microplate reader analysis relative to control	2013	Bioorganic & medicinal chemistry letters, Dec-15, Volume: 23, Issue:24	Synthesis, antioxidant capacity, and structure-activity relationships of tri-O-methylnorbergenin analogues on tyrosinase inhibition.
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.
AID549267	Antioxidant activity assessed as reducing capacity of the compound up to 100 ug/ml after 20 mins	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano).
AID566699	Inhibition of mushroom tyrosinase at 1 mM after 10 mins	2011	Journal of medicinal chemistry, Jan-27, Volume: 54, Issue:2	Identifying chelators for metalloprotein inhibitors using a fragment-based approach.
AID549274	Antioxidant activity in mouse BNL-CL2 cells assessed as inhibition of H2O2-induced ROS production at 20 ug/ml by DCFHDA assay	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano).
AID388743	Antioxidant activity assessed as DPPH radical scavenging activity after 20 mins	2008	Bioorganic & medicinal chemistry, Dec-01, Volume: 16, Issue:23	Inhibition of aldose reductase from cataracted eye lenses by finger millet (Eleusine coracana) polyphenols.
AID1244911	Cytotoxicity against human HL7702 cells after 48 hrs by MTT assay	2015	European journal of medicinal chemistry, Sep-18, Volume: 102	Antitumor activity of endoperoxide-iron chelator conjugates-design, synthesis and biological evaluation.
AID758944	Binding affinity to human LXRbeta-LBD by surface plasmon resonance	2013	Bioorganic & medicinal chemistry letters, Jul-15, Volume: 23, Issue:14	Cyanidin, a natural flavonoid, is an agonistic ligand for liver X receptor alpha and beta and reduces cellular lipid accumulation in macrophages and hepatocytes.
AID1371027	Cytotoxicity against human HeLa cells assessed as reduction in cell viability incubated for 72 hrs by WST-8 dye based assay	2017	Journal of natural products, 04-28, Volume: 80, Issue:4	α-Glucosidase Inhibitory and Cytotoxic Taxane Diterpenoids from the Stem Bark of Taxus wallichiana.
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.
AID1082335	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 0.125% under dark conditions measured 5 to 60 min post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID1449742	Selectivity ratio of Ki for recombinant human carbonic anhydrase 2 to Ki for recombinant Malassezia globosa beta-carbonic anhydrase	2017	Bioorganic & medicinal chemistry, 05-01, Volume: 25, Issue:9	Inhibition of Malassezia globosa carbonic anhydrase with phenols.
AID1082337	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 0.5% under dark conditions measured 5 to 60 min post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID566705	Inhibition of human recombinant MMP8 at 1 mM after 30 mins	2011	Journal of medicinal chemistry, Jan-27, Volume: 54, Issue:2	Identifying chelators for metalloprotein inhibitors using a fragment-based approach.
AID1082357	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 0.125% under light conditions measured 24 hr post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID360324	Antiplasmodial activity after 24 hrs against chloroquine-sensitive, mefloquine-resistant Plasmodium falciparum D6 infected human erythrocytes by [G-3H]hypoxanthine uptake	2001	Journal of natural products, May, Volume: 64, Issue:5	In vitro antiplasmodial activity of extracts of Tristaniopsis species and identification of the active constituents: ellagic acid and 3,4,5-trimethoxyphenyl-(6'-O-galloyl)-O-beta-D-glucopyranoside.
AID549266	Antioxidant activity assessed as trolox equivalent of ABTS radical scavenging activity after 12 to 16 hrs	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano).
AID1130099	Inhibition of human aromatase using androstenedione as substrate assessed as remaining estrone level at 10 uM after 30 mins by LC-MS/MS analysis relative to control	2014	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 24, Issue:7	Inhibitory effect of Rhus verniciflua Stokes extract on human aromatase activity; butin is its major bioactive component.
AID549270	Antioxidant activity in mouse liver assessed as inhibition of Fe2+/ascorbate-induced lipid peroxidation up to 20 ug/ml by TBARS assay relative to control	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano).
AID1082360	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 1% under light conditions measured 24 hr post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID546250	Antimelanogenic activity in mouse B16 cells assessed as decrease in tyrosinase expression at 20 ug/ml after 72 hrs by Western blotting	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano).
AID729536	Inhibition of human carbonic anhydrase 7 preincubated for 15 mins by CO2 hydration stopped-flow assay	2013	Bioorganic & medicinal chemistry, Mar-15, Volume: 21, Issue:6	Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV.
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
AID338331	Antiplatelet activity against rat platelet rich plasma assessed as inhibition of collagen-induced platelet aggregation pretreated 2 mins before collagen challenge
AID614103	Antimicrobial activity against Candida albicans ATCC 10231 after 24 hrs using thiazoyl blue by agar overlay bioautography method	2011	Bioorganic & medicinal chemistry, Sep-01, Volume: 19, Issue:17	Tylosema esculentum extractives and their bioactivity.
AID1313261	Inhibition of chymotrypsin like activity of 20S proteasome (unknown origin) using suc-leu-leu-val-tyr-AMC as substrate at 10 uM after 40 mins in presence of calcium by fluorescence assay	2016	Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15	Cupriphilic compounds to aid in proteasome inhibition.
AID1592385	Electrochemical behavior of the compound assessed as redox potential corrected toward saturated Ag/AgCl reference electrode by cyclic voltammetry
AID1082350	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 0.25% under dark conditions measured 24 hr post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID385427	Inhibition of soybean 15-lipoxygenase	2008	Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8	Inhibition of 15-lipoxygenase-catalysed oxygenation of arachidonic acid by substituted benzoic acids.
AID1082340	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 5% under dark conditions measured 5 to 60 min post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID375988	Antioxidant activity assessed as DPPH free radical scavenging activity relative to control	2006	Journal of natural products, Apr, Volume: 69, Issue:4	Vanillic acid glycoside and quinic acid derivatives from Gardeniae Fructus.
AID549285	Antimelanogenic activity in mouse B16 cells assessed as decrease in TRP2 expression at 20 ug/ml after 72 hrs by flow cytometry assay	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano).
AID566701	Inhibition of recombinant anthrax lethal factor at 1 mM after 30 mins by fluorescence assay	2011	Journal of medicinal chemistry, Jan-27, Volume: 54, Issue:2	Identifying chelators for metalloprotein inhibitors using a fragment-based approach.
AID1126662	Antioxidant activity assessed as DPPH radical scavenging activity by spectrophotometry	2014	European journal of medicinal chemistry, May-06, Volume: 78	One-pot synthesis and radical scavenging activity of novel polyhydroxylated 3-arylcoumarins.
AID1082344	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 1% under light conditions measured 5 to 60 min post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID614101	Antimicrobial activity against Bacillus subtilis ATCC 6633 after 24 hrs using thiazoyl blue by agar overlay bioautography method	2011	Bioorganic & medicinal chemistry, Sep-01, Volume: 19, Issue:17	Tylosema esculentum extractives and their bioactivity.
AID397155	Antioxidant activity against Cu2+-induced lipid peroxidation in human plasma LDL at 0.2 umol/L preincubated for 1 hr before Cu2+ challenge	2001	Journal of natural products, Apr, Volume: 64, Issue:4	Specific antioxidant activity of caffeoyl derivatives and other natural phenolic compounds: LDL protection against oxidation and decrease in the proinflammatory lysophosphatidylcholine production.
AID280290	Inhibition of human E-selectin after 2 hrs at 100 uM	2007	Journal of medicinal chemistry, Mar-22, Volume: 50, Issue:6	Rational design of novel, potent small molecule pan-selectin antagonists.
AID721517	Displacement of 2OG from catalytic domain of PHD2 (181 to 426) (unknown origin) Zn2 expressed in Escherichia coli at 150 uM	2013	Journal of medicinal chemistry, Jan-24, Volume: 56, Issue:2	Reporter ligand NMR screening method for 2-oxoglutarate oxygenase inhibitors.
AID1313260	Inhibition of chymotrypsin like activity of 20S proteasome (unknown origin) using suc-leu-leu-val-tyr-AMC as substrate at 10 uM after 40 mins in presence of nickel by fluorescence assay	2016	Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15	Cupriphilic compounds to aid in proteasome inhibition.
AID1082351	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 0.5% under dark conditions measured 24 hr post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID614104	Antimicrobial activity against Escherichia coli ATCC 11229 after 24 hrs using thiazoyl blue by agar overlay bioautography method	2011	Bioorganic & medicinal chemistry, Sep-01, Volume: 19, Issue:17	Tylosema esculentum extractives and their bioactivity.
AID1439493	Nematocidal activity against Meloidogyne incognita second-stage juveniles after 3 days by light microscopic method	2017	European journal of medicinal chemistry, Mar-31, Volume: 129	Medicinal plants used as anthelmintics: Ethnomedical, pharmacological, and phytochemical studies.
AID566700	Inhibition of human recombinant 5-lipoxygenase at 1 mM after 10 mins by fluorescence assay	2011	Journal of medicinal chemistry, Jan-27, Volume: 54, Issue:2	Identifying chelators for metalloprotein inhibitors using a fragment-based approach.
AID1417130	Antitrypanosomal activity against Trypanosoma brucei rhodesiense STIB 900 trypomastigotes after 72 hrs by Alamar Blue assay	2018	European journal of medicinal chemistry, Sep-05, Volume: 157	Natural products as inhibitors of Leishmania major dihydroorotate dehydrogenase.
AID1464282	Antineuroinflammatory activity in mouse BV2 cells assessed as inhibition of LPS-induced NO production after 24 hrs in presence of LPS by Griess reaction based assay	2017	Bioorganic & medicinal chemistry letters, 10-15, Volume: 27, Issue:20	Natural neuro-inflammatory inhibitors from Caragana turfanensis.
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.
AID566703	Inhibition of human recombinant MMP2 at 1 mM after 30 mins	2011	Journal of medicinal chemistry, Jan-27, Volume: 54, Issue:2	Identifying chelators for metalloprotein inhibitors using a fragment-based approach.
AID549280	Effect on nuclear morphology of mouse B16 cells at 20 ug/ml after 72 hrs by Hoechst 33342 staining in presence of alpha-MSH	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano).
AID566704	Inhibition of human recombinant MMP3 at 1 mM after 30 mins	2011	Journal of medicinal chemistry, Jan-27, Volume: 54, Issue:2	Identifying chelators for metalloprotein inhibitors using a fragment-based approach.
AID725981	Inhibition of CMG2 (40 to 217) C175A and R40C double mutant (unknown origin) interaction to full length PA E733C mutant expressed in Escherichia coli by FRET assay	2013	Journal of medicinal chemistry, Mar-14, Volume: 56, Issue:5	1,2,3,4,6-Penta-O-galloyl-β-D-glucopyranose inhibits angiogenesis via inhibition of capillary morphogenesis gene 2.
AID1675090	Binding affinity to rat DNA polymerase beta with methyl-lysine modification at 72 assessed as inhibition of dRP excision in presence of 32P-end labelled duplex DNA at 50 uM by SDS PAGE	2020	Bioorganic & medicinal chemistry, 09-01, Volume: 28, Issue:17	An assay for DNA polymerase β lyase inhibitors that engage the catalytic nucleophile for binding.
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.
AID549273	Antioxidant activity in mouse brain assessed as inhibition of Fe2+/ascorbate-induced lipid peroxidation up to 100 ug/ml by TBARS assay relative to control	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano).
AID1082330	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 0.5% under dark conditions measured 48 hr post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID1082334	Nematicidal activity against Heterodera zeae infective stage larvae assessed as nematode mortality at 0.5% under light conditions measured 48 hr post dose by stereoscopic microscopy	2011	Journal of agricultural and food chemistry, Sep-14, Volume: 59, Issue:17	Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae.
AID647818	Antifilarial activity against adult Brugia malayi at 31.25 ug/ml by MTT assay relative to control	2012	European journal of medicinal chemistry, Apr, Volume: 50	Galactolipids from Bauhinia racemosa as a new class of antifilarial agents against human lymphatic filarial parasite, Brugia malayi.
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.
AID729533	Inhibition of human carbonic anhydrase 14 preincubated for 15 mins by CO2 hydration stopped-flow assay	2013	Bioorganic & medicinal chemistry, Mar-15, Volume: 21, Issue:6	Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV.
AID1675089	Binding affinity to rat DNA polymerase beta with homo-lysine modification at 72 assessed as inhibition of dRP excision in presence of 32P-end labelled duplex DNA at 50 uM by SDS PAGE	2020	Bioorganic & medicinal chemistry, 09-01, Volume: 28, Issue:17	An assay for DNA polymerase β lyase inhibitors that engage the catalytic nucleophile for binding.
AID607497	Inhibition of Dicentrarchus labrax CA using 4-nitrophenylacetate substrate by esterase assay	2011	Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14	In vitro inhibition of α-carbonic anhydrase isozymes by some phenolic compounds.
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).
AID611698	Inhibition of Escherichia coli beta-glucuronidase assessed as inhibition of p-nitrophenyl-beta-D-glucuronide hydrolysis at 0.20 mM preincubated for 30 mins measured 30 mins after substrate addition by spectrophotometry	2011	Journal of natural products, Jun-24, Volume: 74, Issue:6	Isoflavone dimers and other bioactive constituents from the figs of Ficus mucuso.
AID1424231	Antioxidant activity assessed as DPPH free radical scavenging activity	2017	European journal of medicinal chemistry, Jun-16, Volume: 133	Free radicals and polyphenols: The redox chemistry of neurodegenerative diseases.
AID549277	Inhibition of tyrosinase in mouse B16 cells at 10 to 20 ug/ml after 72 hrs by spectrophotometry	2010	Journal of natural products, Nov-29, Volume: 73, Issue:11	Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano).
AID568365	Inhibition of human carbonic anhydrase 12 preincubated for 15 mins by CO2 hydration stopped-flow assay	2011	Bioorganic & medicinal chemistry, Feb-15, Volume: 19, Issue:4	Kinetic and docking studies of phenol-based inhibitors of carbonic anhydrase isoforms I, II, IX and XII evidence a new binding mode within the enzyme active site.
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.
AID614102	Antimicrobial activity against Pseudomonas aeruginosa NCTC 10332 after 24 hrs using thiazoyl blue by agar overlay bioautography method	2011	Bioorganic & medicinal chemistry, Sep-01, Volume: 19, Issue:17	Tylosema esculentum extractives and their bioactivity.
AID1799773	SPA Assay from Article 10.1016/j.abb.2004.02.039: \\Inhibition of fucosyltransferase VII by gallic acid and its derivatives.\\	2004	Archives of biochemistry and biophysics, May-01, Volume: 425, Issue:1	Inhibition of fucosyltransferase VII by gallic acid and its derivatives.
AID1803326	α-glucosidase Inhibitory Activity Assay from Article 10.3109/14756366.2012.719503: \\Structure-activity relationships of bergenin derivatives effect on a-glucosidase inhibition.\\	2013	Journal of enzyme inhibition and medicinal chemistry, Dec, Volume: 28, Issue:6	Structure-activity relationships of bergenin derivatives effect on α-glucosidase inhibition.
AID1800197	Xanthine Oxidase Activity from Article 10.1111/cbdd.12205: \\Antioxidant, a-glucosidase and xanthine oxidase inhibitory activity of bioactive compounds from maize (Zea mays L.).\\	2014	Chemical biology & drug design, Jan, Volume: 83, Issue:1	Antioxidant, α-glucosidase and xanthine oxidase inhibitory activity of bioactive compounds from maize (Zea mays L.).
AID1799825	Inhibition Assay from Article : \\Partial identity of the 2-oxoglutarate and ascorbate binding sites of prolyl 4-hydroxylase.\\	1986	The Journal of biological chemistry, Jun-15, Volume: 261, Issue:17	Partial identity of the 2-oxoglutarate and ascorbate binding sites of prolyl 4-hydroxylase.
AID1800198	Alpha-Glucosidase Assay from Article 10.1111/cbdd.12205: \\Antioxidant, a-glucosidase and xanthine oxidase inhibitory activity of bioactive compounds from maize (Zea mays L.).\\	2014	Chemical biology & drug design, Jan, Volume: 83, Issue:1	Antioxidant, α-glucosidase and xanthine oxidase inhibitory activity of bioactive compounds from maize (Zea mays L.).
AID977611	Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB	2013	Nucleic acids research, Apr-01, Volume: 41, Issue:6	Study of PcaV from Streptomyces coelicolor yields new insights into ligand-responsive MarR family transcription factors.
AID977611	Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB	2005	Biochemistry, Aug-23, Volume: 44, Issue:33	Roles of the equatorial tyrosyl iron ligand of protocatechuate 3,4-dioxygenase in catalysis.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	50 (5.34)	18.7374
1990's	73 (7.79)	18.2507
2000's	241 (25.72)	29.6817
2010's	417 (44.50)	24.3611
2020's	156 (16.65)	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	9 (0.93%)	5.53%
Reviews	18 (1.87%)	6.00%
Case Studies	1 (0.10%)	4.05%
Observational	1 (0.10%)	0.25%
Other	936 (96.99%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (1)

Trial Overview

Trial			Phase	Enrollment	Study Type	Start Date	Status
Effect of Protocatechuic Acid on Biochemical Markers of Immunity Status in Healthy Adults [NCT06121362]				50 participants (Anticipated)	Interventional	2023-12-31	Not yet recruiting
[information is prepared from clinicaltrials.gov, extracted Sep-2024]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
2,3-dihydroxybenzoic acid 2,3-dihydroxybenzoic acid: RN given refers to parent cpd. dihydroxybenzoic acid : Any member of the class of hydroxybenzoic acids carrying two phenolic hydroxy groups on the benzene ring and its derivatives.. 2,3-dihydroxybenzoic acid : A dihydroxybenzoic acid that is benzoic acid substituted by hydroxy groups at positions 2 and 3. It occurs naturally in Phyllanthus acidus and in the aquatic fern Salvinia molesta.	5	12	0	dihydroxybenzoic acid	human xenobiotic metabolite; plant metabolite
alpha-ketoglutaric acid 2-oxoglutaric acid : An oxo dicarboxylic acid that consists of glutaric acid bearing an oxo substituent at position 2. It is an intermediate metabolite in Krebs cycle.	2.08	1	0	oxo dicarboxylic acid	fundamental metabolite
3-oxoadipic acid 3-oxoadipic acid: RN given refers to parent cpd. 3-oxoadipic acid : An oxo dicarboxylic acid consisting of adipic acid having a single oxo group at the 3-position.	5.29	17	0	dicarboxylic fatty acid; oxo dicarboxylic acid	bacterial xenobiotic metabolite; human metabolite
3-hydroxybenzaldehyde [no description available]	2.03	1	0	hydroxybenzaldehyde
4-hydroxybenzyl alcohol 4-hydroxybenzyl alcohol: the aglycone of gastrodin. p-hydroxybenzyl alcohol : A member of the class of benzyl alcohols that is benzyl alcohol substituted by a hydroxy group at position 4. It has been isolated from Arcangelisia gusanlung.	2.48	2	0	benzyl alcohols; phenols	plant metabolite
4-hydroxybenzaldehyde [no description available]	3.14	5	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.	2.13	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.	11.8	78	0	monohydroxybenzoic acid	algal metabolite; plant metabolite
ethylene glycol Ethylene Glycol: A colorless, odorless, viscous dihydroxy alcohol. It has a sweet taste, but is poisonous if ingested. Ethylene glycol is the most important glycol commercially available and is manufactured on a large scale in the United States. It is used as an antifreeze and coolant, in hydraulic fluids, and in the manufacture of low-freezing dynamites and resins.. ethanediol : Any diol that is ethane or substituted ethane carrying two hydroxy groups.. ethylene glycol : A 1,2-glycol compound produced via reaction of ethylene oxide with water.	5.08	2	1	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.	3.01	4	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).	2.01	1	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]	2.06	1	0	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
adipic acid adipic acid : An alpha,omega-dicarboxylic acid that is the 1,4-dicarboxy derivative of butane.	2.6	1	0	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	food acidity regulator; human xenobiotic metabolite
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.	2.15	1	0	aminobenzoic acid	human metabolite; mouse metabolite
benzaldehyde [no description available]	2.46	2	0	benzaldehydes	EC 3.1.1.3 (triacylglycerol lipase) inhibitor; EC 3.5.5.1 (nitrilase) inhibitor; flavouring agent; fragrance; odorant receptor agonist; plant metabolite
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.	5.29	16	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.	2.04	1	0	benzyl alcohols	antioxidant; fragrance; metabolite; solvent
2,3-butylene glycol 2,3-butylene glycol: RN given refers to cpd without isomeric designation. butane-2,3-diol : A butanediol in which hydroxylation is at C-2 and C-3.	2.08	1	0	butanediol; glycol; secondary alcohol
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.	2.48	2	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.	2.07	1	0	fatty acid 4:0; straight-chain saturated fatty acid	human urinary metabolite; Mycoplasma genitalium metabolite
catechol [no description available]	6.02	37	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).	4.93	2	1	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
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.	4.07	4	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.	2.41	2	0	halide anion; monoatomic chlorine	cofactor; Escherichia coli metabolite; human metabolite
coumarin 2H-chromen-2-one: coumarin derivative	2.51	2	0	coumarins	fluorescent dye; human metabolite; plant metabolite
cuminaldehyde cuminaldehyde : A member of the class of benzaldehydes that is benzaldehyde substituted by an isopropyl group at position 4. It is a component of essential oils from Cumin and exhibits insecticidal activities.	2.03	1	0	benzaldehydes	insecticide; plant metabolite; volatile oil component
4-hydroxymandelic acid 4-hydroxymandelic acid: RN given refers to cpd without isomeric designation. 4-hydroxymandelic acid : A 2-hydroxy carboxylic acid that is mandelic acid bearing a phenolic hydroxy substituent at position 4.	1.97	1	0	2-hydroxy carboxylic acid; phenols	metabolite
salicylic acid Scalp: The outer covering of the calvaria. It is composed of several layers: SKIN; subcutaneous connective tissue; the occipitofrontal muscle which includes the tendinous galea aponeurotica; loose connective tissue; and the pericranium (the PERIOSTEUM of the SKULL).	5.48	20	0	monohydroxybenzoic acid	algal metabolite; antifungal agent; antiinfective agent; EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor; keratolytic drug; plant hormone; plant metabolite
digallic acid digallic acid: structure given in first source	2.08	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.	2.45	2	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.	2.81	3	0	benzenetriol; phenolic donor	algal metabolite
gallic acid gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.	10.55	110	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
hydrogen sulfide Hydrogen Sulfide: A flammable, poisonous gas with a characteristic odor of rotten eggs. It is used in the manufacture of chemicals, in metallurgy, and as an analytical reagent. (From Merck Index, 11th ed). hydrogen sulfide : A sulfur hydride consisting of a single sulfur atom bonded to two hydrogen atoms. A highly poisonous, flammable gas with a characteristic odour of rotten eggs, it is often produced by bacterial decomposition of organic matter in the absence of oxygen.. thiol : An organosulfur compound in which a thiol group, -SH, is attached to a carbon atom of any aliphatic or aromatic moiety.	5.09	1	1	gas molecular entity; hydracid; mononuclear parent hydride; sulfur hydride	Escherichia coli metabolite; genotoxin; metabolite; signalling molecule; toxin; vasodilator agent
4-aminophenol 4-aminophenol: RN given refers to parent cpd. 4-aminophenol : An amino phenol (one of the three possible isomers) which has the single amino substituent located para to the phenolic -OH group.	2.15	1	0	aminophenol	allergen; metabolite
3-chlorobenzoic acid [no description available]	2.43	2	0	monochlorobenzoic acid	drug 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.	2.44	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.	2.08	1	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.	2.79	3	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.	2.68	3	0	catechols; dihydroxyphenylacetic acid	human metabolite
glucono-1,4-lactone [no description available]	1.96	1	0	gamma-lactone
lactic acid Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.	7.46	2	0	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
dimethyl sulfoxide Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.	5.1	2	1	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	2.02	1	0	aldehyde; one-carbon compound	allergen; carcinogenic agent; disinfectant; EC 3.5.1.4 (amidase) inhibitor; environmental contaminant; Escherichia coli metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
glycine [no description available]	4.13	4	0	alpha-amino acid; amino acid zwitterion; proteinogenic amino acid; serine family amino acid	EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor; fundamental metabolite; hepatoprotective agent; micronutrient; neurotransmitter; NMDA receptor agonist; nutraceutical
glycerol Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.	5.03	2	1	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.	2.05	1	0	carbon oxoanion	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
histamine [no description available]	5.09	1	1	aralkylamino compound; imidazoles	human metabolite; mouse metabolite; neurotransmitter
homogentisic acid Homogentisic Acid: Dihydroxyphenylacetic acid with hydroxyls at the 2 and 5 positions of the phenyl ring.. homogentisic acid : A dihydroxyphenylacetic acid having the two hydroxy substituents at the 2- and 5-positions.	2.07	1	0	dihydroxyphenylacetic acid; hydroquinones	human metabolite; plant metabolite
hydrogen Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.	4.94	2	1	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
hydroquinone [no description available]	3.28	6	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.	2.05	1	0	indole-3-acetic acids; monocarboxylic acid	auxin; human metabolite; mouse metabolite; plant hormone; plant metabolite
dihydroxyphenylalanine Dihydroxyphenylalanine: A beta-hydroxylated derivative of phenylalanine. The D-form of dihydroxyphenylalanine has less physiologic activity than the L-form and is commonly used experimentally to determine whether the pharmacological effects of LEVODOPA are stereospecific.. dopa : A hydroxyphenylalanine carrying hydroxy substituents at positions 3 and 4 of the benzene ring.	2.68	3	0	hydroxyphenylalanine; non-proteinogenic alpha-amino acid; tyrosine derivative	human metabolite
kynurenine Kynurenine: A metabolite of the essential amino acid tryptophan metabolized via the tryptophan-kynurenine pathway.. kynurenine : A ketone that is alanine in which one of the methyl hydrogens is substituted by a 2-aminobenzoyl group.	7.6	1	0	aromatic ketone; non-proteinogenic alpha-amino acid; substituted aniline	human metabolite
malonic acid malonic acid : An alpha,omega-dicarboxylic acid in which the two carboxy groups are separated by a single methylene group.. dicarboxylic acid : Any carboxylic acid containing two carboxy groups.	2.15	1	0	alpha,omega-dicarboxylic acid	human 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.	4.17	16	0	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
melatonin [no description available]	10.2	2	1	acetamides; tryptamines	anticonvulsant; central nervous system depressant; geroprotector; hormone; human metabolite; immunological adjuvant; mouse metabolite; radical scavenger
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.	5.28	3	1	metal allergen; nickel group element atom	epitope; micronutrient
niacin Niacin: A water-soluble vitamin of the B complex occurring in various animal and plant tissues. It is required by the body for the formation of coenzymes NAD and NADP. It has PELLAGRA-curative, vasodilating, and antilipemic properties.. vitamin B3 : Any member of a group of vitamers that belong to the chemical structural class called pyridines that exhibit biological activity against vitamin B3 deficiency. Vitamin B3 deficiency causes a condition known as pellagra whose symptoms include depression, dermatitis and diarrhea. The vitamers include nicotinic acid and nicotinamide (and their ionized and salt forms).. nicotinic acid : A pyridinemonocarboxylic acid that is pyridine in which the hydrogen at position 3 is replaced by a carboxy group.	2.43	2	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.	2.46	2	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
nitrous oxide Nitrous Oxide: Nitrogen oxide (N2O). A colorless, odorless gas that is used as an anesthetic and analgesic. High concentrations cause a narcotic effect and may replace oxygen, causing death by asphyxia. It is also used as a food aerosol in the preparation of whipping cream.. dinitrogen oxide : A nitrogen oxide consisting of linear unsymmetrical molecules with formula N2O. While it is the most used gaseous anaesthetic in the world, its major commercial use, due to its solubility under pressure in vegetable fats combined with its non-toxicity in low concentrations, is as an aerosol spray propellant and aerating agent for canisters of 'whipped' cream.	2.97	1	0	gas molecular entity; nitrogen oxide	analgesic; bacterial metabolite; food packaging gas; food propellant; general anaesthetic; greenhouse gas; inhalation anaesthetic; NMDA receptor antagonist; raising agent; refrigerant; vasodilator agent
1-octanol 1-Octanol: A colorless, slightly viscous liquid used as a defoaming or wetting agent. It is also used as a solvent for protective coatings, waxes, and oils, and as a raw material for plasticizers. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). octan-1-ol : An octanol carrying the hydroxy group at position 1.	2.42	2	0	octanol; primary alcohol	antifungal agent; bacterial metabolite; fuel additive; kairomone; plant metabolite
hydroxide ion [no description available]	2.76	2	0	oxygen hydride	mouse metabolite
orotic acid Orotic Acid: An intermediate product in PYRIMIDINE synthesis which plays a role in chemical conversions between DIHYDROFOLATE and TETRAHYDROFOLATE.. orotic acid : A pyrimidinemonocarboxylic acid that is uracil bearing a carboxy substituent at position C-6.	2.17	1	0	pyrimidinemonocarboxylic acid	Escherichia coli metabolite; metabolite; mouse metabolite
oxaloacetic acid Oxaloacetic Acid: A dicarboxylic acid ketone that is an important metabolic intermediate of the CITRIC ACID CYCLE. It can be converted to ASPARTIC ACID by ASPARTATE TRANSAMINASE.. oxaloacetic acid : An oxodicarboxylic acid that is succinic acid bearing a single oxo group.	2.44	2	0	C4-dicarboxylic acid; oxo dicarboxylic acid	geroprotector; 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.	2.07	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.	2.37	2	0	aminobenzoic acid; aromatic amino-acid zwitterion	allergen; Escherichia coli metabolite; plant metabolite
palmitic acid Palmitic Acid: A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids.. hexadecanoic acid : A straight-chain, sixteen-carbon, saturated long-chain fatty acid.	2.99	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
phenanthrene phenanthrene : A polycyclic aromatic hydrocarbon composed of three fused benzene rings which takes its name from the two terms 'phenyl' and 'anthracene.'	2.7	3	0	ortho-fused polycyclic arene; ortho-fused tricyclic hydrocarbon; phenanthrenes	environmental contaminant; mouse metabolite
phenol [no description available]	3.62	8	0	phenols	antiseptic drug; disinfectant; human xenobiotic metabolite; mouse metabolite
phenylpyruvic acid phenylpyruvic acid: RN given refers to parent cpd. phenylpyruvate : A 2-oxo monocarboxylic acid anion resulting from deprotonation of the carboxy group of either keto- or enol-phenylpyruvic acid.. keto-phenylpyruvic acid : A 2-oxo monocarboxylic acid that is 3-phenylpropanoic acid substituted by an oxo group at position 2. It is an intermediate metabolite in the phenylalanine pathway.	2.15	1	0	2-oxo monocarboxylic acid	chromogenic compound; EC 6.4.1.1 (pyruvate carboxylase) inhibitor; fundamental metabolite
phenylacetic acid phenylacetic acid : A monocarboxylic acid that is toluene in which one of the hydrogens of the methyl group has been replaced by a carboxy group.	2.39	2	0	benzenes; monocarboxylic acid; phenylacetic acids	allergen; Aspergillus metabolite; auxin; EC 6.4.1.1 (pyruvate carboxylase) inhibitor; Escherichia coli metabolite; human metabolite; plant growth retardant; plant metabolite; Saccharomyces cerevisiae metabolite; toxin
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.	2.46	2	0	phosphoric acids	algal metabolite; fertilizer; human metabolite; NMR chemical shift reference compound; solvent
phthalic acid phthalic acid: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7178. phthalic acid : A benzenedicarboxylic acid cosisting of two carboxy groups at ortho positions.	3.27	6	0	benzenedicarboxylic acid	human xenobiotic metabolite
picolinic acid picolinic acid: iron-chelating agent that inhibits DNA synthesis; may interfere with iron-dependent production of stable free organic radical which is essential for ribonucleotide reductase formation of deoxyribonucleotides; RN given refers to parent cpd; structure in Merck Index, 9th ed, #7206. picolinic acid : A pyridinemonocarboxylic acid in which the carboxy group is located at position 2. It is an intermediate in the metabolism of tryptophan.	2.06	1	0	pyridinemonocarboxylic acid	human metabolite; MALDI matrix material
pyrogallol benzenetriol : A triol in which three hydroxy groups are substituted onto a benzene ring.	4.68	6	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.	2.42	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.	2.06	1	0	pyridinedicarboxylic acid	Escherichia coli metabolite; human metabolite; mouse metabolite; NMDA receptor agonist
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).	5.27	3	1	divalent inorganic anion; sulfur oxide; sulfur oxoanion
spermine [no description available]	2.06	1	0	polyazaalkane; tetramine	antioxidant; fundamental metabolite; immunosuppressive agent
succinic acid Succinic Acid: A water-soluble, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. (Hawley's Condensed Chemical Dictionary, 12th ed, p1099; McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed, p1851). succinic acid : An alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle.	3.17	5	0	alpha,omega-dicarboxylic acid; C4-dicarboxylic acid	anti-ulcer drug; fundamental metabolite; micronutrient; nutraceutical; radiation protective agent
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.	7.47	2	0	primary alcohol; vitamin B1	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
uracil 2,4-dihydroxypyrimidine: a urinary biomarker for bipolar disorder	5.09	1	1	pyrimidine nucleobase; pyrimidone	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; prodrug; Saccharomyces cerevisiae 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.	5.21	3	1	uric acid	Escherichia coli metabolite; human metabolite; mouse 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).	3.75	10	0	benzaldehydes; monomethoxybenzene; phenols	anti-inflammatory agent; anticonvulsant; antioxidant; flavouring agent; plant metabolite
xanthine 7H-xanthine : An oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-7 is protonated.. 9H-xanthine : An oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-9 is protonated.	2.01	1	0	xanthine	Saccharomyces cerevisiae 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.	2.08	1	0	secondary alcohol; tricarboxylic acid	fundamental metabolite
catechin [no description available]	2.44	2	0	hydroxyflavan
vanilmandelic acid Vanilmandelic Acid: A 3-O-methyl ether of 3,4-dihydroxymandelic acid. It is an end-stage metabolite of CATECHOLAMINES; EPINEPHRINE; and NOREPINEPHRINE.. vanillylmandelic acid : An aromatic ether that is the 3-O-methyl ether of 3,4-dihydroxymandelic acid.	1.97	1	0	2-hydroxy monocarboxylic acid; aromatic ether; phenols	human metabolite
mandelic acid SAMMA: mandelic acid condensation polymer	1.96	1	0	2-hydroxy monocarboxylic acid; benzenes	antibacterial agent; human xenobiotic metabolite
1,10-phenanthroline 1,10-phenanthroline: RN given refers to parent cpd; inhibits Zn-dependent metalloproteinases	2.06	1	0	phenanthroline	EC 2.7.1.1 (hexokinase) inhibitor; EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor
1-anilino-8-naphthalenesulfonate 1-anilino-8-naphthalenesulfonate: RN given refers to parent cpd. 8-anilinonaphthalene-1-sulfonic acid : A naphthalenesulfonic acid that is naphthalene-1-sulfonic acid substituted by a phenylamino group at position 8.	2.78	3	0	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
2,4-dichlorophenoxyacetic acid 2,4-Dichlorophenoxyacetic Acid: An herbicide with irritant effects on the eye and the gastrointestinal system.. 2,4-D : A chlorophenoxyacetic acid that is phenoxyacetic acid in which the ring hydrogens at postions 2 and 4 are substituted by chlorines.	1.96	1	0	chlorophenoxyacetic acid; dichlorobenzene	agrochemical; defoliant; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; environmental contaminant; phenoxy herbicide; synthetic auxin
beta-resorcylic acid beta-resorcylic acid: RN given refers to parent cpd; structure	3.64	9	0
2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine: mutagen from fried ground beef; structure given in first source. PhIP : An imidazopyridine that is 1H--imidazo[4,5-b]pyridine which is substituted at positions 1, 2, and 6 by methyl, amino, and phenyl groups, respectively. It is the most abundant of the mutagenic heterocyclic amines found in cooked meat and fish.	2.46	2	0	imidazopyridine; primary amino compound	carcinogenic agent; mutagen
pyrithione pyrithione: split from cephalosporin molecule; some metal complexes of this have fumarate reductase inhibitory activity and may be useful against trypanosomes; RN given refers to parent cpd; structure. pyrithione : A pyridinethione that is pyridine-2(1H)-thione in which the hydrogen attached to the nitrogen is replaced by a hydroxy group. It is a Zn(2+) ionophore; the zinc salt is used as an antifungal and antibacterial agent.	2.06	1	0	monohydroxypyridine; pyridinethione	ionophore
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.	2.42	2	0	ortho- and peri-fused polycyclic arene	aryl hydrocarbon receptor agonist; carcinogenic agent
3-nitropropionic acid 3-nitropropionic acid: succinate dehydrogenase inactivator; biosynthesized by FABACEAE plants from ASPARAGINE. 3-nitropropanoic acid : A C-nitro compound that is propanoic acid in which one of the methyl hydrogens has been replaced by a nitro group.	2.4	2	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.	2.49	2	0	guaiacols; monocarboxylic acid	human metabolite; mouse metabolite
5-fluoroindole-2-carboxylic acid 5-fluoroindole-2-carboxylic acid: N-methyl-D-aspartate receptor antagonist	2.54	2	0	indolyl carboxylic acid
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.	5.04	2	1	monohydroxyquinoline	antibacterial agent; antifungal agrochemical; antiseptic drug; iron chelator
tacrine Tacrine: A cholinesterase inhibitor that crosses the blood-brain barrier. Tacrine has been used to counter the effects of muscle relaxants, as a respiratory stimulant, and in the treatment of Alzheimer's disease and other central nervous system disorders.. tacrine : A member of the class of acridines that is 1,2,3,4-tetrahydroacridine substituted by an amino group at position 9. It is used in the treatment of Alzheimer's disease.	2.41	1	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	1.98	1	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.	2.15	1	0	acetamides; phenols	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; cyclooxygenase 3 inhibitor; environmental contaminant; ferroptosis inducer; geroprotector; hepatotoxic agent; human blood serum metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
acetazolamide Acetazolamide: One of the CARBONIC ANHYDRASE INHIBITORS that is sometimes effective against absence seizures. It is sometimes useful also as an adjunct in the treatment of tonic-clonic, myoclonic, and atonic seizures, particularly in women whose seizures occur or are exacerbated at specific times in the menstrual cycle. However, its usefulness is transient often because of rapid development of tolerance. Its antiepileptic effect may be due to its inhibitory effect on brain carbonic anhydrase, which leads to an increased transneuronal chloride gradient, increased chloride current, and increased inhibition. (From Smith and Reynard, Textbook of Pharmacology, 1991, p337)	2.78	3	0	monocarboxylic acid amide; sulfonamide; thiadiazoles	anticonvulsant; diuretic; EC 4.2.1.1 (carbonic anhydrase) inhibitor
acetohydroxamic acid acetohydroxamic acid: urease inhibitor. oxime : Compounds of structure R2C=NOH derived from condensation of aldehydes or ketones with hydroxylamine. Oximes from aldehydes may be called aldoximes; those from ketones may be called ketoximes.. N-hydroxyacetimidic acid : A carbohydroximic acid consisting of acetimidic acid having a hydroxy group attached to the imide nitrogen.. acetohydroxamic acid : A member of the class of acetohydroxamic acids that is acetamide in which one of the amino hydrogens has been replaced by a hydroxy group.	2.5	2	0	acetohydroxamic acids; carbohydroximic acid	algal metabolite; EC 3.5.1.5 (urease) inhibitor
alachlor alachlor : An aromatic amide that is N-(2,6-diethylphenyl)acetamide substituted by a methoxymethyl group at at the nitrogen atom while one of the hydrogens of the methyl group has been replaced by a chlorine atom.	7.11	1	0	aromatic amide; monocarboxylic acid amide; organochlorine compound	environmental contaminant; herbicide; xenobiotic
am 251 AM 251: an analog of SR141716A; structure given in first source. AM-251 : A carbohydrazide obtained by formal condensation of the carboxy group of 1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid with the amino group of 1-aminopiperidine. An antagonist at the CB1 cannabinoid receptor.	2.21	1	0	amidopiperidine; carbohydrazide; dichlorobenzene; organoiodine compound; pyrazoles	antidepressant; antineoplastic agent; apoptosis inducer; CB1 receptor antagonist
theophylline [no description available]	2.46	2	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
acetovanillone apocynin : An aromatic ketone that is 1-phenylethanone substituted by a hydroxy group at position 4 and a methoxy group at position 3.	2.74	3	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
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.	2.06	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.	4.4	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
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.	2.25	1	0	ortho- and peri-fused polycyclic arene	carcinogenic agent; mouse metabolite
butylbenzyl phthalate spatozoate: structure in first source	2.04	1	0	benzyl ester
berberine [no description available]	2.05	1	0	alkaloid antibiotic; berberine alkaloid; botanical anti-fungal agent; organic heteropentacyclic compound	antilipemic drug; antineoplastic agent; antioxidant; EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor; EC 1.21.3.3 (reticuline oxidase) inhibitor; EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor; EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor; EC 2.7.11.10 (IkappaB kinase) inhibitor; EC 3.1.1.4 (phospholipase A2) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; geroprotector; hypoglycemic agent; metabolite; potassium channel blocker
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.	2	1	0	extended flavonoid; naphtho-gamma-pyrone; organic heterotricyclic compound	aryl hydrocarbon receptor agonist
caffeine [no description available]	2.46	2	0	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
camphor, (+-)-isomer [no description available]	2.03	1	0	bornane monoterpenoid; cyclic monoterpene ketone	plant metabolite
carbofuran Carbofuran: A cholinesterase inhibitor that is used as a systemic insecticide, an acaricide, and nematocide. (From Merck Index, 11th ed)	2.06	1	0	1-benzofurans; carbamate ester	acaricide; agrochemical; avicide; carbamate insecticide; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; nematicide
cetyl alcohol cetyl alcohol: has been used for eczema, skin irritations; RN given refers to parent cpd; structure. hexadecanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of sixteen carbon atoms.. hexadecan-1-ol : A long-chain primary fatty alcohol that is hexadecane substituted by a hydroxy group at position 1.	2.06	1	0	hexadecanol; long-chain primary fatty alcohol	algal metabolite; flavouring agent; human metabolite; plant metabolite
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.	2	1	0	aminoquinoline; organochlorine compound; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; antirheumatic drug; autophagy inhibitor; dermatologic drug
chromone-2-carboxylic acid [no description available]	2.15	1	0	chromones
ciprofloxacin Ciprofloxacin: A broad-spectrum antimicrobial carboxyfluoroquinoline.. ciprofloxacin : A quinolone that is quinolin-4(1H)-one bearing cyclopropyl, carboxylic acid, fluoro and piperazin-1-yl substituents at positions 1, 3, 6 and 7, respectively.	2.05	1	0	aminoquinoline; cyclopropanes; fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone; zwitterion	antibacterial drug; antiinfective agent; antimicrobial agent; DNA synthesis inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; environmental contaminant; topoisomerase IV inhibitor; xenobiotic
cloxyquin cloxyquin: has antitubercular activity; structure in first source	2.06	1	0	organochlorine compound; quinolines
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.	3.78	3	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.	2.17	1	0	aromatic ether; cyclopropanecarboxylate ester; nitrile; organochlorine compound	agrochemical; molluscicide; pyrethroid ester acaricide; pyrethroid ester insecticide
deferoxamine Deferoxamine: Natural product isolated from Streptomyces pilosus. It forms iron complexes and is used as a chelating agent, particularly in the mesylate form.. desferrioxamine B : An acyclic desferrioxamine that is butanedioic acid in which one of the carboxy groups undergoes formal condensation with the primary amino group of N-(5-aminopentyl)-N-hydroxyacetamide and the second carboxy group undergoes formal condensation with the hydroxyamino group of N(1)-(5-aminopentyl)-N(1)-hydroxy-N(4)-[5-(hydroxyamino)pentyl]butanediamide. It is a siderophore native to Streptomyces pilosus biosynthesised by the DesABCD enzyme cluster as a high affinity Fe(III) chelator.	2.47	2	0	acyclic desferrioxamine	bacterial metabolite; ferroptosis inhibitor; iron chelator; siderophore
eflornithine Eflornithine: An inhibitor of ORNITHINE DECARBOXYLASE, the rate limiting enzyme of the polyamine biosynthetic pathway.. eflornithine : A fluoroamino acid that is ornithine substituted by a difluoromethyl group at position 2.	2	1	0	alpha-amino acid; fluoroamino acid	trypanocidal drug
dibenzothiophene dibenzothiophene : A mancude organic heterotricyclic parent that consists of a thiophene ring flanked by two benzene rings ortho-fused across the 2,3- and 4,5-positions.	2.46	2	0	dibenzothiophenes; mancude organic heterotricyclic parent	keratolytic drug
dibutyl phthalate Dibutyl Phthalate: A plasticizer used in most plastics and found in water, air, soil, plants and animals. It may have some adverse effects with long-term exposure.. dibutyl phthalate : A phthalate ester that is the diester obtained by the formal condensation of the carboxy groups of phthalic acid with two molecules of butan-1-ol. Although used extensively as a plasticiser, it is a ubiquitous environmental contaminant that poses a risk to humans.	2.44	2	0	diester; phthalate ester	EC 3.2.1.20 (alpha-glucosidase) inhibitor; environmental contaminant; metabolite; plasticiser; teratogenic 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.	2.54	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
diethylcarbamazine Diethylcarbamazine: An anthelmintic used primarily as the citrate in the treatment of filariasis, particularly infestations with Wucheria bancrofti or Loa loa.	2.07	1	0	N-carbamoylpiperazine; N-methylpiperazine
disulfiram [no description available]	2.77	3	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
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.	2.1	1	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.	5.09	1	1
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.	2.06	1	0	aromatic carboxylic acid; pyridines
vanoxerine vanoxerine: structure given in first source. vanoxerine : An N-alkylpiperazine that consists of piperazine bearing 2-bis(4-fluorophenyl)methoxy]ethyl and 3-phenylpropyl groups at positions 1 and 4 respectively. Potent, competitive inhibitor of dopamine uptake (Ki = 1 nM for inhibition of striatal dopamine uptake). Has > 100-fold lower affinity for the noradrenalin and 5-HT uptake carriers. Also a potent sigma ligand (IC50 = 48 nM). Centrally active following systemic administration.	2.04	1	0	ether; N-alkylpiperazine; organofluorine compound; tertiary amino compound	dopamine uptake inhibitor
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.	6.37	21	0	dihydroxybenzoic acid	EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; fungal metabolite; human metabolite; MALDI matrix material; mouse metabolite
glyburide Glyburide: An antidiabetic sulfonylurea derivative with actions like those of chlorpropamide. glyburide : An N-sulfonylurea that is acetohexamide in which the acetyl group is replaced by a 2-(5-chloro-2-methoxybenzamido)ethyl group.	2.53	2	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
beta-thujaplicin beta-thujaplicin: structure. beta-thujaplicin : A monoterpenoid that is cyclohepta-2,4,6-trien-1-one substituted by a hydroxy group at position 2 and an isopropyl group at position 4. Isolated from Thuja plicata and Chamaecyparis obtusa, it exhibits antimicrobial activities.	2.06	1	0	cyclic ketone; enol; monoterpenoid	antibacterial agent; antifungal agent; antineoplastic agent; antiplasmodial drug; plant metabolite
ethidium Ethidium: A trypanocidal agent and possible antiviral agent that is widely used in experimental cell biology and biochemistry. Ethidium has several experimentally useful properties including binding to nucleic acids, noncompetitive inhibition of nicotinic acetylcholine receptors, and fluorescence among others. It is most commonly used as the bromide.. ethidium : The fluorescent compound widely used in experimental cell biology and biochemistry to reveal double-stranded DNA and RNA.	2.01	1	0	phenanthridines	fluorochrome; intercalator
indole-3-carbinol indole-3-carbinol: occurs in edible cruciferous vegetables. indole-3-methanol : An indolyl alcohol carrying a hydroxymethyl group at position 3. It is a constituent of the cruciferous vegetables and had anticancer activity.	2.44	2	0	indolyl alcohol	antineoplastic agent; plant metabolite
isoflurane Isoflurane: A stable, non-explosive inhalation anesthetic, relatively free from significant side effects.	2.04	1	0	organofluorine compound	inhalation anaesthetic
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.	3.16	3	0	catechols; secondary alcohol; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; cardiotonic drug; sympathomimetic agent
ketamine Ketamine: A cyclohexanone derivative used for induction of anesthesia. Its mechanism of action is not well understood, but ketamine can block NMDA receptors (RECEPTORS, N-METHYL-D-ASPARTATE) and may interact with sigma receptors.. ketamine : A member of the class of cyclohexanones in which one of the hydrogens at position 2 is substituted by a 2-chlorophenyl group, while the other is substituted by a methylamino group.	2.04	1	0	cyclohexanones; monochlorobenzenes; secondary amino compound	analgesic; environmental contaminant; intravenous anaesthetic; neurotoxin; NMDA receptor antagonist; xenobiotic
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.	7.21	1	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
kojic acid [no description available]	3.34	6	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
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.	2.02	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; antibacterial agent; plant metabolite
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	2.07	1	0	biphenylyltetrazole; imidazoles	angiotensin receptor antagonist; anti-arrhythmia drug; antihypertensive agent; endothelin receptor 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	2.08	1	0	chromones; morpholines; organochlorine compound	autophagy inhibitor; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor; geroprotector
mefloquine hydrochloride [2,8-bis(trifluoromethyl)quinolin-4-yl]-(2-piperidyl)methanol : An organofluorine compound that consists of quinoline bearing trifluoromethyl substituents at positions 2 and 8 as well as a (2-piperidinyl)hydroxymethyl substituent at position 4.	2	1	0	organofluorine compound; piperidines; quinolines; secondary alcohol
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.	2.25	1	0	1,4-naphthoquinones; vitamin K	angiogenesis inhibitor; antineoplastic agent; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; human urinary metabolite; nutraceutical
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.	2.15	1	0	amino acid; aromatic amine; monocarboxylic acid; monohydroxybenzoic acid; phenols	non-steroidal anti-inflammatory drug
methyl methanesulfonate [no description available]	2	1	0	methanesulfonate ester	alkylating agent; apoptosis inducer; carcinogenic agent; genotoxin; mutagen
metronidazole Metronidazole: A nitroimidazole used to treat AMEBIASIS; VAGINITIS; TRICHOMONAS INFECTIONS; GIARDIASIS; ANAEROBIC BACTERIA; and TREPONEMAL INFECTIONS.. metronidazole : A member of the class of imidazoles substituted at C-1, -2 and -5 with 2-hydroxyethyl, nitro and methyl groups respectively. It has activity against anaerobic bacteria and protozoa, and has a radiosensitising effect on hypoxic tumour cells. It may be given by mouth in tablets, or as the benzoate in an oral suspension. The hydrochloride salt can be used in intravenous infusions. Metronidazole is a prodrug and is selective for anaerobic bacteria due to their ability to intracellularly reduce the nitro group of metronidazole to give nitroso-containing intermediates. These can covalently bind to DNA, disrupting its helical structure, inducing DNA strand breaks and inhibiting bacterial nucleic acid synthesis, ultimately resulting in bacterial cell death.	2.04	1	0	C-nitro compound; imidazoles; primary alcohol	antiamoebic agent; antibacterial drug; antimicrobial agent; antiparasitic agent; antitrichomonal drug; environmental contaminant; prodrug; radiosensitizing agent; xenobiotic
5-nitro-2-(3-phenylpropylamino)benzoic acid 5-nitro-2-(3-phenylpropylamino)benzoic acid: structure given in first source; chloride channel antagonist	2.6	1	0	nitrobenzoic acid
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.	7.37	2	0	aminobenzoic acid; phenols	antitubercular agent
quinone benzoquinone : The simplest members of the class of benzoquinones, consisting of cyclohexadiene which is substituted by two oxo groups.. 1,4-benzoquinone : The simplest member of the class of 1,4-benzoquinones, obtained by the formal oxidation of hydroquinone to the corresponding diketone. It is a metabolite of benzene.. quinone : Compounds having a fully conjugated cyclic dione structure, such as that of benzoquinones, derived from aromatic compounds by conversion of an even number of -CH= groups into -C(=O)- groups with any necessary rearrangement of double bonds (polycyclic and heterocyclic analogues are included).	2.71	3	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.	2.01	1	0	dimethylxanthine	central nervous system stimulant; human blood serum metabolite; human xenobiotic metabolite; mouse 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'.	2.05	1	0	aromatic amine; monomethoxyflavone	EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector
pentoxifylline [no description available]	7.31	1	0	oxopurine
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.	7.21	1	0	barbiturates	anticonvulsant; drug allergen; excitatory amino acid antagonist; sedative
piracetam Piracetam: A compound suggested to be both a nootropic and a neuroprotective agent.	2.07	1	0	organonitrogen compound; organooxygen compound
4-aminobenzoic acid para-Aminobenzoates: Benzoic acids, salts, or esters that contain an amino group attached to carbon number 4 of the benzene ring structure.. 4-aminobenzoate : An aromatic amino-acid anion that is the conjugate base of 4-aminobenzoic acid.	2.05	1	0	aminobenzoate; aromatic amino-acid anion	Escherichia coli metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
probucol Probucol: A drug used to lower LDL and HDL cholesterol yet has little effect on serum-triglyceride or VLDL cholesterol. (From Martindale, The Extra Pharmacopoeia, 30th ed, p993).. probucol : A dithioketal that is propane-2,2-dithiol in which the hydrogens attached to both sulfur atoms are replaced by 3,5-di-tert-butyl-4-hydroxyphenyl groups. An anticholesteremic drug with antioxidant and anti-inflammatory properties, it is used to treat high levels of cholesterol in blood.	2	1	0	dithioketal; polyphenol	anti-inflammatory drug; anticholesteremic drug; antilipemic drug; antioxidant; cardiovascular drug
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.	6.97	1	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.	2.96	4	0	trihydroxybenzoic acid
resorcinol resorcinol: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7951. resorcinol : A benzenediol that is benzene dihydroxylated at positions 1 and 3.	8.24	6	0	benzenediol; phenolic donor; resorcinols	erythropoietin inhibitor; sensitiser
salicyl alcohol salicyl alcohol: RN given refers to parent cpd; saligenin is the aglycone of salicin; structure; it is oxidatively metabolized to gentisic acid. salicyl alcohol : A hydroxybenzyl alcohol that is phenol substituted by a hydroxymethyl group at C-2.	2.15	1	0	aromatic primary alcohol; hydroxybenzyl alcohol	human urinary metabolite
salicylamide salamide: a major impurity of hydrochlorothiazide; structure in first source	2.06	1	0	phenols; salicylamides	antirheumatic drug; non-narcotic analgesic
sevoflurane Sevoflurane: A non-explosive inhalation anesthetic used in the induction and maintenance of general anesthesia. It does not cause respiratory irritation and may also prevent PLATELET AGGREGATION.. sevoflurane : An ether compound having fluoromethyl and 1,1,1,3,3,3-hexafluoroisopropyl as the two alkyl groups.	7.25	1	0	ether; organofluorine compound	central nervous system depressant; inhalation anaesthetic; platelet aggregation inhibitor
sulfadiazine Sulfadiazine: One of the short-acting SULFONAMIDES used in combination with PYRIMETHAMINE to treat toxoplasmosis in patients with acquired immunodeficiency syndrome and in newborns with congenital infections.. sulfadiazine : A sulfonamide consisting of pyrimidine with a 4-aminobenzenesulfonamido group at the 2-position.. diazine : The parent structure of the diazines.	5.09	1	1	pyrimidines; substituted aniline; sulfonamide antibiotic; sulfonamide	antiinfective agent; antimicrobial agent; antiprotozoal drug; coccidiostat; drug allergen; EC 1.1.1.153 [sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming)] inhibitor; EC 2.5.1.15 (dihydropteroate synthase) inhibitor; environmental contaminant; xenobiotic
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.	2.46	2	0	long-chain fatty acid; saturated fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; human metabolite; plant metabolite
sulfamethoxazole Sulfamethoxazole: A bacteriostatic antibacterial agent that interferes with folic acid synthesis in susceptible bacteria. Its broad spectrum of activity has been limited by the development of resistance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p208). sulfamethoxazole : An isoxazole (1,2-oxazole) compound having a methyl substituent at the 5-position and a 4-aminobenzenesulfonamido group at the 3-position.	2.05	1	0	isoxazoles; substituted aniline; sulfonamide antibiotic; sulfonamide	antibacterial agent; antiinfective agent; antimicrobial agent; drug allergen; EC 1.1.1.153 [sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming)] inhibitor; EC 2.5.1.15 (dihydropteroate synthase) inhibitor; environmental contaminant; epitope; P450 inhibitor; xenobiotic
sulfapyridine Sulfapyridine: Antibacterial, potentially toxic, used to treat certain skin diseases.. sulfapyridine : A sulfonamide consisting of pyridine with a 4-aminobenzenesulfonamido group at the 2-position.	2.03	1	0	pyridines; substituted aniline; sulfonamide antibiotic; sulfonamide	antiinfective agent; dermatologic drug; drug allergen; environmental contaminant; xenobiotic
sulforaphane sulforaphane: from Cardaria draba L.. sulforaphane : An isothiocyanate having a 4-(methylsulfinyl)butyl group attached to the nitrogen.	2.13	1	0	isothiocyanate; sulfoxide	antineoplastic agent; antioxidant; EC 3.5.1.98 (histone deacetylase) inhibitor; plant metabolite
theobromine Theobromine: 3,7-Dimethylxanthine. The principle alkaloid in Theobroma cacao (the cacao bean) and other plants. A xanthine alkaloid that is used as a bronchodilator and as a vasodilator. It has a weaker diuretic activity than THEOPHYLLINE and is also a less powerful stimulant of smooth muscle. It has practically no stimulant effect on the central nervous system. It was formerly used as a diuretic and in the treatment of angina pectoris and hypertension. (From Martindale, The Extra Pharmacopoeia, 30th ed, pp1318-9). theobromine : A dimethylxanthine having the two methyl groups located at positions 3 and 7. A purine alkaloid derived from the cacao plant, it is found in chocolate, as well as in a number of other foods, and is a vasodilator, diuretic and heart stimulator.	2.01	1	0	dimethylxanthine	adenosine receptor antagonist; bronchodilator agent; food component; human blood serum metabolite; mouse metabolite; plant metabolite; vasodilator agent
2-thiosalicylic acid 2-thiosalicylic acid: a degradation product of thimerosal; RN given refers to parent cpd. thiosalicylic acid : A sulfanylbenzoic acid that is the 2-sulfanyl derivative of benzoic acid.	2.15	1	0	sulfanylbenzoic acid	antipyretic; non-narcotic analgesic
triclosan [no description available]	5.04	2	1	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
trimethoprim Trimethoprim: A pyrimidine inhibitor of dihydrofolate reductase, it is an antibacterial related to PYRIMETHAMINE. It is potentiated by SULFONAMIDES and the TRIMETHOPRIM, SULFAMETHOXAZOLE DRUG COMBINATION is the form most often used. It is sometimes used alone as an antimalarial. TRIMETHOPRIM RESISTANCE has been reported.. trimethoprim : An aminopyrimidine antibiotic whose structure consists of pyrimidine 2,4-diamine and 1,2,3-trimethoxybenzene moieties linked by a methylene bridge.	2.05	1	0	aminopyrimidine; methoxybenzenes	antibacterial drug; diuretic; drug allergen; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; environmental contaminant; xenobiotic
tyramine [no description available]	2.06	1	0	monoamine molecular messenger; primary amino compound; tyramines	EC 3.1.1.8 (cholinesterase) inhibitor; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter
xylazine Xylazine: An adrenergic alpha-2 agonist used as a sedative, analgesic and centrally acting muscle relaxant in VETERINARY MEDICINE.. xylazine : A methyl benzene that is 1,3-dimethylbenzene which is substituted by a 5,6-dihydro-4H-1,3-thiazin-2-ylnitrilo group at position 2. It is an alpha2 adrenergic receptor agonist and frequently used in veterinary medicine as an emetic and sedative with analgesic and muscle relaxant properties.	2.04	1	0	1,3-thiazine; methylbenzene; secondary amino compound	alpha-adrenergic agonist; analgesic; emetic; muscle relaxant; sedative
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.	5.09	1	1	mitomycin	alkylating agent; antineoplastic agent
corticosterone [no description available]	2.58	2	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
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.	2.72	3	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
2-aminophenol [no description available]	2.43	2	0	aminophenol	bacterial metabolite
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.	2.17	1	0	pilocarpine	antiglaucoma drug
diethylnitrosamine Diethylnitrosamine: A nitrosamine derivative with alkylating, carcinogenic, and mutagenic properties.. N-nitrosodiethylamine : A nitrosamine that is N-ethylethanamine substituted by a nitroso group at the N-atom.	2.95	4	0	nitrosamine	carcinogenic agent; hepatotoxic agent; mutagen
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.	2.8	3	0	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
desoxycorticosterone acetate Desoxycorticosterone Acetate: The 21-acetate derivative of desoxycorticosterone.	2.17	1	0	corticosteroid hormone
4-nitroquinoline-1-oxide 4-nitroquinoline N-oxide : A quinoline N-oxide carrying a nitro substituent at position 4.	2.39	2	0	C-nitro compound; quinoline N-oxide	carcinogenic agent
chloramphenicol Amphenicol: Chloramphenicol and its derivatives.	2.4	2	0	C-nitro compound; carboxamide; diol; organochlorine compound	antibacterial drug; antimicrobial agent; Escherichia coli metabolite; geroprotector; Mycoplasma genitalium metabolite; protein synthesis inhibitor
sucrose Saccharum: A plant genus of the family POACEAE widely cultivated in the tropics for the sweet cane that is processed into sugar.	2.48	2	0	glycosyl glycoside	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; sweetening agent
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.	2.69	3	0	ortho-fused polycyclic arene; tetraphenes	carcinogenic agent
adenosine diphosphate Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.	2.08	1	0	adenosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	fundamental metabolite; human metabolite
2,3,4,6-tetrachlorophenol 2,3,4,6-tetrachlorophenol: RN given refers to parent cpd; see also record for tetrachlorophenol with locants for chloro groups not specified. 2,3,4,6-tetrachlorophenol : A tetrachlorophenol in which the chlorines are located at positions 2, 3, 4, and 6.	2.02	1	0	tetrachlorophenol	xenobiotic metabolite
bromodeoxyuridine Bromodeoxyuridine: A nucleoside that substitutes for thymidine in DNA and thus acts as an antimetabolite. It causes breaks in chromosomes and has been proposed as an antiviral and antineoplastic agent. It has been given orphan drug status for use in the treatment of primary brain tumors.	2.42	2	0	pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent
galactose galactopyranose : The pyranose form of galactose.	5.35	3	1	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.	5.8	3	1	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.	2.13	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	3.3	2	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.	2.03	1	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.	2.96	4	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.	2.13	1	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; proteinogenic amino acid; tyrosine	EC 1.3.1.43 (arogenate dehydrogenase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
cysteamine Cysteamine: A mercaptoethylamine compound that is endogenously derived from the COENZYME A degradative pathway. The fact that cysteamine is readily transported into LYSOSOMES where it reacts with CYSTINE to form cysteine-cysteamine disulfide and CYSTEINE has led to its use in CYSTINE DEPLETING AGENTS for the treatment of CYSTINOSIS.. cysteamine : An amine that consists of an ethane skeleton substituted with a thiol group at C-1 and an amino group at C-2.	2.06	1	0	amine; thiol	geroprotector; human metabolite; mouse metabolite; radiation protective agent
phlorhizin [no description available]	2.1	1	0	aryl beta-D-glucoside; dihydrochalcones; monosaccharide derivative	antioxidant; plant metabolite
adenosine monophosphate Adenosine Monophosphate: Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position.	1.98	1	0	adenosine 5'-phosphate; purine ribonucleoside 5'-monophosphate	adenosine A1 receptor agonist; cofactor; EC 3.1.3.1 (alkaline phosphatase) inhibitor; EC 3.1.3.11 (fructose-bisphosphatase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
methylene blue Methylene Blue: A compound consisting of dark green crystals or crystalline powder, having a bronze-like luster. Solutions in water or alcohol have a deep blue color. Methylene blue is used as a bacteriologic stain and as an indicator. It inhibits GUANYLATE CYCLASE, and has been used to treat cyanide poisoning and to lower levels of METHEMOGLOBIN.. methylene blue : An organic chloride salt having 3,7-bis(dimethylamino)phenothiazin-5-ium as the counterion. A commonly used dye that also exhibits antioxidant, antimalarial, antidepressant and cardioprotective properties.	2.02	1	0	organic chloride salt	acid-base indicator; antidepressant; antimalarial; antimicrobial agent; antioxidant; cardioprotective agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 4.6.1.2 (guanylate cyclase) inhibitor; fluorochrome; histological dye; neuroprotective agent; physical tracer
methacholine chloride Methacholine Chloride: A quaternary ammonium parasympathomimetic agent with the muscarinic actions of ACETYLCHOLINE. It is hydrolyzed by ACETYLCHOLINESTERASE at a considerably slower rate than ACETYLCHOLINE and is more resistant to hydrolysis by nonspecific CHOLINESTERASES so that its actions are more prolonged. It is used as a parasympathomimetic bronchoconstrictor agent and as a diagnostic aid for bronchial asthma. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1116)	2.08	1	0	quaternary ammonium salt
dimethylnitrosamine Dimethylnitrosamine: A nitrosamine derivative with alkylating, carcinogenic, and mutagenic properties. It causes serious liver damage and is a hepatocarcinogen in rodents.	2.1	1	0	nitrosamine	geroprotector; mutagen
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.	3.65	2	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
ficusin Ficusin: A naturally occurring furocoumarin, found in PSORALEA. After photoactivation with UV radiation, it binds DNA via single and double-stranded cross-linking.. psoralen : The simplest member of the class of psoralens that is 7H-furo[3,2-g]chromene having a keto group at position 7. It has been found in plants like Psoralea corylifolia and Ficus salicifolia.	3.25	1	0	psoralens	plant metabolite
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.	2.1	1	0	chloromethanes; one-carbon compound	carcinogenic agent; central nervous system drug; inhalation anaesthetic; non-polar solvent; refrigerant
trifluridine Trifluridine: An antiviral derivative of THYMIDINE used mainly in the treatment of primary keratoconjunctivitis and recurrent epithelial keratitis due to HERPES SIMPLEX virus. (From Martindale, The Extra Pharmacopoeia, 30th ed, p557). trifluridine : A pyrimidine 2'-deoxyribonucleoside compound having 5-trifluoromethyluracil as the nucleobase. An antiviral drug used mainly in the treatment of primary keratoconjunctivitis and recurrent epithelial keratitis.	5.09	1	1	nucleoside analogue; organofluorine compound; pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent; antiviral drug; EC 2.1.1.45 (thymidylate synthase) inhibitor
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.	2.25	1	0	C-nitro compound; organofluorine compound	agrochemical; allergen; chromatographic reagent; EC 2.7.3.2 (creatine kinase) inhibitor; protein-sequencing agent; spectrophotometric reagent
4-toluenesulfonamide 4-toluenesulfonamide: RN given refers to parent cpd. toluene-4-sulfonamide : A sulfonamide that is benzenesulfonamide bearing a methyl group at position 4.	2.06	1	0	sulfonamide
histidine Histidine: An essential amino acid that is required for the production of HISTAMINE.. L-histidine : The L-enantiomer of the amino acid histidine.. histidine : An alpha-amino acid that is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3.	2.41	1	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
chlorquinaldol Chlorquinaldol: Local anti-infective agent used for skin, gastrointestinal, and vaginal infections with fungi, protozoa, and certain bacteria. In animals, it causes central nervous system damage and is not administered parenterally. It is also used as antiseptic, fungistat, or deodorant.. chlorquinaldol : A monohydroxyquinoline that is quinolin-8-ol which is substituted by a methyl group at position 2 and by chlorine at positions 5 and 7. An antifungal and antibacterial, it was formerly used for topical treatment of skin conditions and vaginal infections.	5.09	1	1	monohydroxyquinoline; organochlorine compound	antibacterial drug; antiprotozoal drug; antiseptic drug
4-chlorobenzoic acid 4-chlorobenzoic acid: RN given refers to parent cpd. 4-chlorobenzoic acid : A monochlorobenzoic acid carrying a chloro substituent at position 4.	2.15	1	0	monochlorobenzoic acid	bacterial xenobiotic 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.	7.31	1	0	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
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.	7.77	3	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.	2.15	1	0	chloromethanes; volatile organic compound	carcinogenic agent; polar aprotic solvent; refrigerant
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.	7.4	2	0	alkyl hydroperoxide	antibacterial agent; oxidising agent
trichloroacetic acid Trichloroacetic Acid: A strong acid used as a protein precipitant in clinical chemistry and also as a caustic for removing warts.. trichloroacetic acid : A monocarboxylic acid that is acetic acid in which all three methyl hydrogens are substituted by chlorine.	2.15	1	0	monocarboxylic acid; organochlorine compound	carcinogenic agent; metabolite; mouse metabolite
quinic acid (-)-quinic acid : The (-)-enantiomer of quinic acid.	4.19	16	0
acrylic acid acrylic acid: RN given refers to parent cpd. acrylic acid : A alpha,beta-unsaturated monocarboxylic acid that is ethene substituted by a carboxy group.	2.02	1	0	alpha,beta-unsaturated monocarboxylic acid	metabolite
peracetic acid Peracetic Acid: A liquid that functions as a strong oxidizing agent. It has an acrid odor and is used as a disinfectant.. peracetic acid : A peroxy acid that is acetic acid in which the OH group is substituted by a hydroperoxy group. It is a versatile oxidising agent that is used as a disinfectant.	2.03	1	0	a peroxy acid	disinfectant; oxidising agent
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	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.	7.6	1	0	bisphenol	endocrine disruptor; environmental contaminant; xenobiotic; xenoestrogen
3-methylsalicylic acid 3-methylsalicylic acid : A monohydroxybenzoic acid consisting of salicylic acid carrying a methyl group at the 3-position.	2.06	1	0	monohydroxybenzoic acid	bacterial xenobiotic metabolite
lawsone lawsone: a molluscacide from leaves of Lawsonia inermis L. topical sunscreening agent; structure; powdered leaves of Lawsonia inermis(Lythraceae) used as brown hair dye. lawsone : 1,4-Naphthoquinone carrying a hydroxy function at C-2. It is obtained from the leaves of Lawsonia inermis.	2.06	1	0
rotenone Derris: A plant genus of the family FABACEAE. The root is a source of rotenoids (ROTENONE) and flavonoids. Some species of Pongamia have been reclassified to this genus and some to MILLETTIA. Some species of Deguelia have been reclassified to this genus.. rotenoid : Members of the class of tetrahydrochromenochromene that consists of a cis-fused tetrahydrochromeno[3,4-b]chromene skeleton and its substituted derivatives. The term was originally restricted to natural products, but is now also used to describe semi-synthetic and fully synthetic compounds.	7.04	1	0	organic heteropentacyclic compound; rotenones	antineoplastic agent; metabolite; mitochondrial NADH:ubiquinone reductase inhibitor; phytogenic insecticide; piscicide; toxin
1-hydroxy-2-naphthoic acid 1-hydroxy-2-naphthoic acid: RN given refers to parent cpd. 1-hydroxy-2-naphthoic acid : A naphthoic acid with the carboxy group at position 2 and carrying a hydroxy substituent at the 1-position. It is a xenobiotic metabolite produced by the biodegradation of phenanthrene by microorganisms.	2.66	2	0	hydroxy monocarboxylic acid; naphthoic acid; naphthols	bacterial xenobiotic metabolite; fungal xenobiotic metabolite
fluorene [no description available]	7.93	4	0	ortho-fused polycyclic arene; ortho-fused tricyclic hydrocarbon
2,6-xylidine 2,6-xylidine: RN given refers to parent cpd. 2,6-dimethylaniline : A primary arylamine that is aniline in which the hydrogens at the 2- and 6-positions are replaced by methyl groups. It is used in the production of some anasthetics and other chemicals. It is a drug metabolite of lidocaine (local anasthetic).	2.01	1	0	dimethylaniline; primary arylamine	carcinogenic agent; drug metabolite
5-methylsalicylic acid [no description available]	2.8	3	0
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.	3.25	1	0	monoterpenoid; phenols	volatile oil component
salicylaldehyde o-hydroxybenzaldehyde: structure in first source	2.03	1	0	hydroxybenzaldehyde	nematicide; plant metabolite
veratrole veratrole: structure. dimethoxybenzene : Any methoxybenzene that consists of a benzene skeleton substituted with two methoxy groups and its derivatives.. veratrole : A dimethoxybenzene with the methoxy groups at ortho-positions.	2.48	2	0	dimethoxybenzene	plant metabolite
uvitex swn Uvitex SWN: optical brightner from Ciba; structure	3.25	1	0	7-aminocoumarins	fluorochrome
xanthenes Xanthenes: Compounds with three aromatic rings in linear arrangement with an OXYGEN in the center ring.	2.44	2	0	xanthene
veratric acid veratric acid: RN given refers to parent cpd; structure. 3,4-dimethoxybenzoic acid : A member of the class of benzoic acids that is benzoic acid substituted by methoxy groups at positions 2 and 3.	8.98	13	0	benzoic acids	allergen; plant metabolite
2-naphthoic acid 2-naphthoic acid: RN given refers to parent cpd. 2-naphthoic acid : A naphthoic acid that is naphthalene carrying a carboxy group at position 2.	2.07	1	0	naphthoic acid	mouse metabolite; xenobiotic metabolite
quinaldic acid [no description available]	2.5	2	0	quinolinemonocarboxylic acid	human metabolite; Saccharomyces cerevisiae metabolite
methyleugenol methyleugenol: structure	3.25	1	0	phenylpropanoid
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)	5.56	68	0	benzoate ester; paraben; phenols	antifungal agent; antimicrobial agent
2,4-dihydroxybenzaldehyde 2,4-dihydroxybenzaldehyde : A dihydroxybenzaldehyde that is resorcinol which has been substituted by a formyl group para to one of the hydroxy groups.	2.46	2	0	dihydroxybenzaldehyde
2-toluidine 2-toluidine: RN given refers to parent cpd. o-toluidine : An aminotoluene in which the amino substituent is ortho to the methyl group.	2.01	1	0	aminotoluene	carcinogenic 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.	2.42	2	0	butan-4-olide	metabolite; neurotoxin
5-nitrosalicylic acid 5-nitrosalicylic acid : A monohydroxybenzoic acid in which the hydroxy group is ortho- to the carboxylic acid group and which has a nitro substituent para- to the phenolic hydroxy group.	2.15	1	0	4-nitrophenols; monohydroxybenzoic acid
sulfosalicylic acid 5-sulfosalicylic acid : An arenesulfonic acid that is benzoic acid substituted by a hydroxy at position C-2 and a sulfo group at C-5.	2.03	1	0	arenesulfonic acid; benzoic acids; phenols	metabolite
ethylene dimethacrylate ethylene glycol dimethacrylate : The enoate ester that is the 1,2-bis(methacryloyl) derivative of ethylene glycol.	2.07	1	0	enoate ester	allergen; cross-linking reagent; polymerisation monomer
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.	2.5	2	0	aldehyde; furans	Maillard reaction product; metabolite
4-tert-butylbenzoic acid 4-tert-butylbenzoic acid: RN given refers to parent cpd	2.03	1	0	alkylbenzene
3-aminobenzoic acid 3-aminobenzoic acid: RN given refers to parent cpd. 3-aminobenzoic acid : An aminobenzoic acid carrying an amino group at position 3.	2.15	1	0	aminobenzoic acid
3-hydroxybenzoic acid 3-hydroxybenzoic acid: RN given refers to parent cpd. 3-hydroxybenzoic acid : A monohydroxybenzoic acid that is benzoic acid substituted by a hydroxy group at position 3. It has been isolated from Taxus baccata. It is used as an intermediate in the synthesis of plasticisers, resins, pharmaceuticals, etc.	4.1	15	0	monohydroxybenzoic acid	bacterial metabolite; plant metabolite
alpha-resorcylic acid alpha-resorcylic acid: RN given refers to parent cpd. 3,5-dihydroxybenzoic acid : A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 5.	3.53	8	0	dihydroxybenzoic acid; resorcinols	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.	3.57	8	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.	2.46	2	0	paraben	antifungal agent; antimicrobial food preservative; neuroprotective agent; plant metabolite
4-cymene 4-cymene: structure. p-cymene : A monoterpene that is toluene substituted by an isopropyl group at position 4.	3.25	1	0	monoterpene; toluenes	human urinary metabolite; plant metabolite; volatile oil component
4-toluic acid 4-toluic acid: RN given refers to parent cpd; structure. p-toluic acid : A methylbenzoic acid in which the methyl substituent is located at position 4.	2.4	2	0	methylbenzoic acid
4-chloronitrobenzene [no description available]	2.02	1	0	C-nitro compound
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.	3.31	6	0	methoxybenzoic acid	plant metabolite
4-(dimethylamino)benzaldehyde p-dimethylaminobenzaldehyde: structure in first source. 4-(dimethylamino)benzaldehyde : A member of the class of benzaldehydes that is benzaldehyde carrying a dimethylamino substituent at position 4. Used as an indicator for detection of indoles and hydrazine.	2.03	1	0	benzaldehydes; substituted aniline; tertiary amino compound	chromogenic compound
terephthalic acid terephthalic acid: RN given refers to 1,4-benzenedicarboxylic acid. terephthalic acid : A benzenedicarboxylic acid carrying carboxy groups at positions 1 and 4. One of three possible isomers of benzenedicarboxylic acid, the others being phthalic and isophthalic acids.	2.44	2	0	benzenedicarboxylic acid
2,5-pyridinedicarboxylic acid 2,5-Pyridinedicarboxylic acid: RN given refers to parent cpd. isocinchomeronic acid : A pyridinedicarboxylic acid carrying carboxy groups at positions 2 and 5.	2.06	1	0	pyridinedicarboxylic acid
4-vinylpyridine 4-vinylpyridine: reagent for blocking cysteine function in proteins; RN given refers to parent cpd	2.07	1	0
phenylhydroxylamine phenylhydroxylamine: RN given refers to parent cpd. N-phenylhydroxylamine : An N-substituted amine that is a derivative of aniline in which one of the amino hydrogen atoms is replaced with a hydroxy substituent.	2.01	1	0	N-substituted amine
anisole anisole : A monomethoxybenzene that is benzene substituted by a methoxy group.	2.48	2	0	monomethoxybenzene	plant metabolite
2,4-dimethylphenol 2,4-dimethylphenol: RN given refers to parent cpd. 2,4-xylenol : A member of the class of phenols that phenol substituted by methyl groups at positions 2 and 4.	2.13	1	0	aromatic fungicide; phenols	disinfectant; volatile oil component
4-xylene p-xylene : A xylene with methyl groups at positions 1 and 4.	1.96	1	0	xylene
acrolein [no description available]	2.06	1	0	enal	herbicide; human xenobiotic metabolite; toxin
2-methylpentane Hexanes: Six-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Various polyneuropathies are caused by hexane poisoning.	2.01	1	0	alkane
bromobenzene [no description available]	2.01	1	0	bromoarene; bromobenzenes; volatile organic compound	hepatotoxic agent; mouse metabolite; non-polar solvent
pyrroles 1H-pyrrole : A tautomer of pyrrole that has the double bonds at positions 2 and 4.. pyrrole : A five-membered monocyclic heteroarene comprising one NH and four CH units which forms the parent compound of the pyrrole group of compounds. Its five-membered ring structure has three tautomers. A 'closed class'.. azole : Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen.	5.09	1	1	pyrrole; secondary amine
thiophenes Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.	2.46	2	0	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
1-hexanol 1-hexanol: RN given refers to parent cpd. hexanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of six carbon atoms.. hexan-1-ol : A primary alcohol that is hexane substituted by a hydroxy group at position 1.	2.01	1	0	hexanol; primary alcohol	alarm pheromone; antibacterial agent; fragrance; plant metabolite
heptanol Heptanol: A colorless liquid with a fragrant odor. It is used as an intermediate, solvent and in cosmetics.. heptanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of seven carbon atoms.. heptan-1-ol : A primary alcohol that is heptane substituted by a hydroxy group at position 1. It has been isolated from Capillipedium parviflorum.	2.01	1	0	heptanol; primary alcohol	flavouring agent; fragrance; gap junctional intercellular communication inhibitor; plant metabolite
n-decyl alcohol n-decyl alcohol: RN given refers to parent cpd. decanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of ten carbon atoms.. decan-1-ol : A fatty alcohol consisting of a hydroxy function at C-1 of an unbranched saturated chain of ten carbon atoms.	2.01	1	0	decanol; primary alcohol	metabolite; pheromone; protic solvent
undecan-1-ol undecan-1-ol : A primary alcohol that is undecane substituted by a hydroxy group at position 1.. undecanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of eleven carbon atoms.	2.01	1	0	primary alcohol; undecanol	flavouring agent; plant metabolite
dodecanol Dodecanol: A saturated 12-carbon fatty alcohol obtained from coconut oil fatty acids. It has a floral odor and is used in detergents, lubricating oils, and pharmaceuticals. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). dodecanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of twelve carbon atoms.. dodecan-1-ol : A primary alcohol that is dodecane in which a hydrogen from one of the methyl groups is replaced by a hydroxy group. It is registered for use in apple and pear orchards as a Lepidopteran pheromone/sex attractant, used to disrupt the mating behaviour of certain moths whose larvae destroy crops.	2.01	1	0	dodecanol; primary alcohol	bacterial metabolite; cosmetic; insect attractant; insecticide; pheromone; plant metabolite
1-tridecanol 1-tridecanol: RN given refers to parent cpd. tridecan-1-ol : A long-chain primary fatty alcohol that is tridecane substituted by a hydroxy group at position 1.. tridecanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of thirteen carbon atoms.	2.01	1	0	long-chain primary fatty alcohol; tridecanol	bacterial metabolite; human metabolite; plant metabolite
behenic acid behenic acid: RN given refers to parent cpd; structure. docosanoic acid : A straight-chain, C22, long-chain saturated fatty acid.	2.06	1	0	long-chain fatty acid; straight-chain saturated fatty acid	plant metabolite
desaspidin desaspidin: structure	3.25	1	0
3,4,5-trimethoxybenzoic acid 3,4,5-trimethoxybenzoic acid: RN given refers to parent cpd; structure. 3,4,5-trimethoxybenzoic acid : A benzoic acid derivative carrying 3-, 4- and 5-methoxy substituents.	2.44	2	0	benzoic acids; methoxybenzenes	human urinary metabolite; human xenobiotic metabolite; plant metabolite
maltol maltol: found in bark of young larch trees; isolated from Passiflora incarnata; possesses depressant properties in mice; potentiates hexobarbital-induced narcosis & inhibits spontaneous motor activity; structure	2.06	1	0	4-pyranones	metabolite
scoparone scoparone: structure. scoparone : A member of the class of coumarins that is esculetin in which the two hydroxy groups at positions 6 and 7 are replaced by methoxy groups. It is a major constituent of the Chinese herbal medicine Yin Chen Hao, and exhibits a variety of pharmacological activities such as anti-inflammatory, anti-allergic, and anti-tumor activities.	2.73	3	0	aromatic ether; coumarins	anti-allergic agent; anti-inflammatory agent; antihypertensive agent; antilipemic drug; immunosuppressive agent; plant metabolite
anthracene acene : A polycyclic aromatic hydrocarbon consisting of fused benzene rings in a rectilinear arrangement.. acenes : Polycyclic aromatic hydrocarbons consisting of fused benzene rings in a rectilinear arrangement and their substitution derivatives.	2.73	3	0	acene; anthracenes; ortho-fused tricyclic hydrocarbon
ethyl-p-hydroxybenzoate ethyl-p-hydroxybenzoate: structure	2.49	2	0	ethyl ester; paraben	antifungal agent; antimicrobial food preservative; phytoestrogen; plant metabolite
vanillic acid Vanillic Acid: A flavoring agent. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13).. vanillic acid : A monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3.	13.35	90	1	methoxybenzoic acid; monohydroxybenzoic acid	plant metabolite
3-nitrobenzoic acid 3-nitrobenzoic acid: RN given refers to parent cpd	1.98	1	0
pyrazolanthrone pyrazolanthrone: JNK (c-Jun N-terminal kinase) inhibitor; structure in first source. anthra[1,9-cd]pyrazol-6(2H)-one : A member of the class of anthrapyrazoles that is anthra[1,9-cd]pyrazole substituted at position 6 by an oxo group. An inhibitor of c-Jun N-terminal kinase.	2.48	2	0	anthrapyrazole; aromatic ketone; cyclic ketone	antineoplastic agent; c-Jun N-terminal kinase inhibitor; geroprotector
monobutyl phthalate monobutyl phthalate: RN given refers to parent cpd	2.03	1	0	phthalic acid monoester
syringaldehyde syringaldehyde: isolated from nonfermented fiber fractions of oat hulls and cottonseed hulls. syringaldehyde : A hydroxybenzaldehyde that is 4-hydroxybenzaldehyde substituted by methoxy groups at positions 3 and 5. Isolated from Pisonia aculeata and Panax japonicus var. major, it exhibits hypoglycemic activity.	2.44	2	0	dimethoxybenzene; hydroxybenzaldehyde	hypoglycemic agent; plant metabolite
2-Methoxybenzaldehyde [no description available]	2.03	1	0	carbonyl compound
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.	2.15	1	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.	6.56	14	1	alpha,beta-unsaturated monocarboxylic acid; cyclohexenecarboxylic acid; hydroxy monocarboxylic acid	Escherichia coli metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
nitrilotriacetic acid Nitrilotriacetic Acid: A derivative of acetic acid, N(CH2COOH)3. It is a complexing (sequestering) agent that forms stable complexes with Zn2+. (From Miall's Dictionary of Chemistry, 5th ed.)	2.01	1	0	NTA; tricarboxylic acid	carcinogenic agent; nephrotoxic agent
protocatechualdehyde protocatechualdehyde: found in wheat grains, wheat seedlings, & other plants; RN given refers to parent cpd; see also rancinamycins; structure	9.86	33	0	dihydroxybenzaldehyde
estragole estragole : A phenylpropanoid that is chavicol in which the hydroxy group is replaced by a methoxy group.	3.25	1	0	alkenylbenzene; monomethoxybenzene; phenylpropanoid	carcinogenic agent; flavouring agent; genotoxin; insect attractant; plant metabolite
ethyl acetate ethyl acetate : The acetate ester formed between acetic acid and ethanol.	8.3	6	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.	2.07	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	human metabolite; plant metabolite
1-nonanol nonanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of nine carbon atoms.. nonan-1-ol : A nonanol that is nonane substituted by a hydroxy group at position 1. It has been isolated as a component of volatile oils from plants like Hordeum vulgare.	2.01	1	0	nonanol; primary alcohol	antifungal agent; flavouring agent; plant metabolite; volatile oil component
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.	2.03	1	0	hydrochloride; organoammonium salt	anti-allergic agent; antiemetic; antiparkinson drug; antipruritic drug; H1-receptor antagonist; local anaesthetic; muscarinic antagonist; sedative
2-vanillin ortho-vanillin : A member of the class of benzaldehydes that is salicylaldehyde substituted by a methoxy group at position 3.	2.03	1	0	benzaldehydes; guaiacols	antimutagen; plant metabolite
mequinol mequinol: depigmenting agent; RN given refers to parent cpd	3.53	2	0	methoxybenzenes; phenols	metabolite
1,4-dimethoxybenzene 1,4-dimethoxybenzene: structure given in first source	2.48	2	0	dimethoxybenzene
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.	7.04	37	0	catechin	antioxidant; plant metabolite
fluoranthene fluoranthene: structure. fluoranthene : An ortho- and peri-fused polycyclic arene consisting of a naphthalene and benzene unit connected by a five-membered ring.	2.46	2	0	ortho- and peri-fused polycyclic arene
thiazoles [no description available]	2.25	1	0	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
hydrazine diamine : Any polyamine that contains two amino groups.	2.43	2	0	azane; hydrazines	EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
gamma-resorcylic acid [no description available]	3.3	6	0	dihydroxybenzoic acid	metabolite
liriodenine liriodenine: structure given in first source. liriodenine : An oxoaporphine alkaloid that is 4,5,6,6a-tetradehydronoraporphin-7-one substituted by a methylenedioxy group across positions 1 and 2. It is isolated from Annona glabra and has been shown to exhibit antimicrobial and cytotoxic activities.	2.02	1	0	alkaloid antibiotic; cyclic ketone; organic heteropentacyclic compound; oxacycle; oxoaporphine alkaloid	antifungal agent; antimicrobial agent; antineoplastic agent; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; metabolite
emetine Emetine: The principal alkaloid of ipecac, from the ground roots of Uragoga (or Cephaelis) ipecacuanha or U. acuminata, of the Rubiaceae. It is used as an amebicide in many different preparations and may cause serious cardiac, hepatic, or renal damage and violent diarrhea and vomiting. Emetine inhibits protein synthesis in EUKARYOTIC CELLS but not PROKARYOTIC CELLS.. emetine : A pyridoisoquinoline comprising emetam having methoxy substituents at the 6'-, 7'-, 10- and 11-positions. It is an antiprotozoal agent and emetic. It inhibits SARS-CoV2, Zika and Ebola virus replication and displays antimalarial, antineoplastic and antiamoebic properties.	2.17	1	0	isoquinoline alkaloid; pyridoisoquinoline	antiamoebic agent; anticoronaviral agent; antiinfective agent; antimalarial; antineoplastic agent; antiprotozoal drug; antiviral agent; autophagy inhibitor; emetic; expectorant; plant metabolite; protein synthesis inhibitor
9-fluorenone fluoren-9-one : The simplest member of the class fluoren-9-ones that is 9H-fluorene bearing an oxo substituent at position 9.	2	1	0	fluoren-9-ones	fungal xenobiotic metabolite
flavanone flavanone: RN given refers to cpd with unspecified isomeric designation; structure in first source. flavanone : The simplest member of the class of flavanones that consists of flavan bearing an oxo substituent at position 4.	2.1	1	0	flavanones
topanol 354 Topanol 354: structure	3.25	1	0	methoxybenzenes; phenols
2,4-pyridinedicarboxylic acid lutidinic acid : A pyridinedicarboxylic acid carrying carboxy groups at positions 2 and 4.	2.08	1	0	pyridinedicarboxylic acid
dipicolinic acid dipicolinic acid : A pyridinedicarboxylic acid carrying two carboxy groups at positions 2 and 6.	2.5	2	0	pyridinedicarboxylic acid	bacterial metabolite
4-hydroxyphenylethanol 4-hydroxyphenylethanol: in chest gland secretion of galagos. 2-(4-hydroxyphenyl)ethanol : A phenol substituted at position 4 by a 2-hydroxyethyl group.	2.4	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.	2.54	2	0	hydroxy monocarboxylic acid	plant metabolite
orcinol orcinol: used as reagent for pentoses, lignin, beet sugar, saccharoses, arabinose & diastase; RN given refers to parent cpd; structure. orcinol : A 5-alkylresorcinol in which the alkyl group is specified as methyl.	2.13	1	0	5-alkylresorcinol; dihydroxytoluene	Aspergillus metabolite
alpha-aminopyridine alpha-aminopyridine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #485. aminopyridine : Compounds containing a pyridine skeleton substituted by one or more amine groups.	2.01	1	0
hexacosanoic acid hexacosanoic acid: a C(26) saturated acid. hexacosanoic acid : A 26-carbon, straight-chain, saturated fatty acid.	2.15	1	0	fatty acid 26:0; straight-chain saturated fatty acid; very long-chain fatty acid
oleanolic acid [no description available]	4.46	6	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	plant metabolite
anemonin anemonin: a furanone dimer found in RANUNCULACEAE; do not confuse with anemonine which is 5-(carboxymethyl)-1,1-dimethylimidazolium hydroxide inner salt; ranunculine is hydrolyzed to protoanemonin which dimerizes to anemonin; structure	2.04	1	0
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.	2.25	1	0	3'-hydroxyflavanones; 4'-methoxyflavanones; dihydroxyflavanone; disaccharide derivative; flavanone glycoside; monomethoxyflavanone; rutinoside	mutagen
luminol Luminol: 5-Amino-2,3-dihydro-1,4-phthalazinedione. Substance that emits light on oxidation. It is used in chemical determinations.	5.24	3	1
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.	2.04	1	0	flavones	metabolite; nematicide
2,4,6-trimethylphenol [no description available]	3.25	1	0	hydroxytoluene
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.	10.68	24	0	benzoic acids; dimethoxybenzene; phenols	plant metabolite
hydroxyhydroquinone benzene-1,2,4-triol : A benzenetriol carrying hydroxy groups at positions 1, 2 and 4.	2.78	3	0	benzenetriol	mouse metabolite
tropolone Tropolone: A seven-membered aromatic ring compound. It is structurally related to a number of naturally occurring antifungal compounds (ANTIFUNGAL AGENTS).. tropolone : A cyclic ketone that is cyclohepta-2,4,6-trien-1-one substituted by a hydroxy group at position 2. It is a toxin produced by the agricultural pathogen Burkholderia plantarii.	2.06	1	0	alpha-hydroxy ketone; cyclic ketone; enol	bacterial metabolite; fungicide; toxin
pyrithiamine Pyrithiamine: A thiamine antagonist due to its inhibition of thiamine pyrophosphorylation. It is used to produce thiamine deficiency.. pyrithiamine : A pyridinium ion that is 3-(2-hydroxyethyl)-2-methylpyridine substituted at position 1 by a (4-amino-2-methylpyrimidin-5-yl)methyl group.	7.6	1	0
methoxyhydroxyphenylglycol Methoxyhydroxyphenylglycol: Synthesized from endogenous epinephrine and norepinephrine in vivo. It is found in brain, blood, CSF, and urine, where its concentrations are used to measure catecholamine turnover.	2.13	1	0	methoxybenzenes; phenols
cumic acid cumic acid : A member of the class of benzoic acids that is cumene substituted by at least one carboxy group.. p-cumic acid : A cumic acid that consists of benzoic acid substituted by an isopropyl group at position 4.	2.03	1	0	cumic acid	plant metabolite
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.	3.63	8	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.	2.06	1	0	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite
trinitrobenzenesulfonic acid Trinitrobenzenesulfonic Acid: A reagent that is used to neutralize peptide terminal amino groups.. 2,4,6-trinitrobenzenesulfonic acid : The arenesulfonic acid that is benzenesulfonic acid with three nitro substituents in the 2-, 4- and 6-positions.	2.15	1	0	arenesulfonic acid; C-nitro compound	epitope; explosive; reagent
paeonol paeonol: structure	2.01	1	0	methoxybenzenes; phenols	metabolite
formestane [no description available]	2.1	1	0	17-oxo steroid; 3-oxo-Delta(4) steroid; enol; hydroxy steroid	antineoplastic agent; EC 1.14.14.14 (aromatase) inhibitor
1,2-dihydroxynaphthalene 1,2-dihydroxynaphthalene: RN given refers to parent cpd	2.06	1	0	naphthalenediol	mouse metabolite
3-hydroxyflavone 3-hydroxyflavone: structure given in first source. flavonol : A monohydroxyflavone that is the 3-hydroxy derivative of flavone.	4.6	7	0	flavonols; monohydroxyflavone
8-aminoquinoline [no description available]	2.06	1	0
3-methoxybenzoic acid [no description available]	2.45	2	0	methoxybenzoic acid	flavouring agent; human urinary metabolite
3-aminophenol 3-aminophenol: RN given refers to parent cpd. 3-aminophenol : An aminophenol that is one of three amino derivatives of phenol which has the single amino substituent located meta to the phenolic -OH group.	2.52	2	0	aminophenol
3-methoxybenzaldehyde 3-methoxybenzaldehyde : A member of the class of benzaldehydes in which the hydrogen at position 3 of benzaldehyde has been replaced by a methoxy group.	2.03	1	0	benzaldehydes; monomethoxybenzene	Brassica napus metabolite
levulinic acid levulinic acid: inhibits 5-aminolevulinic acid dehydratase; RN given refers to parent cpd; structure in Merck Index, 9th ed, #5316. 4-oxopentanoic acid : An oxopentanoic acid with the oxo group in the 4-position.	2.13	1	0	oxopentanoic acid; straight-chain saturated fatty acid	plant metabolite
ethane sulfonate [no description available]	1.99	1	0	alkanesulfonic acid
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).	2	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
2,3,4-Trihydroxybenzoic acid [no description available]	2.03	1	0	hydroxybenzoic acid
2-hydroxyphenylacetic acid 2-hydroxyphenylacetic acid: structure. (2-hydroxyphenyl)acetic acid : A hydroxy monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 2-hydroxyphenyl group. It is a metabolite of phenylalanine and is excreted in the urine of patients suffering from diseases like phenylketonuria.	2.15	1	0	hydroxy monocarboxylic acid; phenols	human metabolite; mouse metabolite
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	3.85	3	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-hydrazinobenzoic acid 4-hydrazinobenzoic acid: structure given in first source	2.15	1	0
5-methyl-2-furfural 5-methyl-2-furfural: RN given refers to cpd with locants as specified	2.5	2	0	aldehyde; furans	EC 2.2.1.6 (acetolactate synthase) inhibitor; flavouring agent; human metabolite; Maillard reaction product
isovanillin isovanillin: inhibits aldehyde oxidase. isovanillin : A member of the class of benzaldehydes that is 4-methoxybenzaldehyde substituted by a hydroxy group at position 3. It is an inhibitor of aldehyde oxidase.	2.43	2	0	benzaldehydes; monomethoxybenzene; phenols	animal metabolite; antidiarrhoeal drug; antifungal agent; EC 1.2.3.1 (aldehyde oxidase) inhibitor; HIV protease inhibitor; plant metabolite
6-methyluracil 6-methyluracil: RN given refers to unlabeled cpd; structure. 6-methyluracil : A pyrimidone that is uracil with a methyl group at position 6.	2.06	1	0	pyrimidone	metabolite
Berberine chloride (TN) [no description available]	2.07	1	0	organic molecular entity
2-pyrrolecarboxylic acid 2-pyrrolecarboxylic acid: hypocalcemic action; structure. pyrrole-2-carboxylic acid : A pyrrolecarboxylic acid that is 1H-pyrrole carrying a carboxy substituent at position 2.	2.06	1	0	pyrrolecarboxylic acid	plant metabolite
4-hydroxyisophthalic acid 4-hydroxyisophthalic acid: structure given in first source	2.13	1	0
isovanillic acid 3-hydroxy-4-methoxybenzoic acid : A methoxybenzoic acid that is 4-methoxybenzoic acid bearing a hydroxy substituent at position 3.	3.97	13	0	methoxybenzoic acid; monohydroxybenzoic acid	antibacterial agent; plant metabolite
methylnitrosourea Methylnitrosourea: A nitrosourea compound with alkylating, carcinogenic, and mutagenic properties.. N-methyl-N-nitrosourea : A member of the class of N-nitrosoureas that is urea in which one of the nitrogens is substituted by methyl and nitroso groups.	1.98	1	0	N-nitrosoureas	alkylating agent; carcinogenic agent; mutagen; teratogenic agent
phenylphosphate phenylphosphate: structure given in first source. phenyl phosphate : An aryl phosphate resulting from the mono-esterification of phosphoric acid with phenol.	2.04	1	0	aryl phosphate	mouse metabolite
4-cyanophenol 4-cyanophenol: reversible monoamine oxidase inhibitor	2.15	1	0	phenols	EC 1.4.3.4 (monoamine oxidase) inhibitor
8-hydroxy-2-methylquinoline 8-hydroxy-2-methylquinoline: structure in first source	2.06	1	0	hydroxyquinoline
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.	2.48	2	0	gallate ester	plant metabolite
2-(2'-hydroxyphenyl)benzoxazole 2-(2'-hydroxyphenyl)benzoxazole: structure in first source. 2-(1,3-benzoxazol-2-yl)phenol : A member of the class of 1,3-benzoxazoles that is 1,3-benzoxazole substituted by a 2-hydroxyphenyl group at position 2.	2.06	1	0	1,3-benzoxazoles; phenols	geroprotector
3-hydroxypicolinic acid [no description available]	2.06	1	0	monocarboxylic acid; monohydroxypyridine	MALDI matrix material
nitrosobenzylmethylamine nitrosobenzylmethylamine: structure	2.1	1	0
8-hydroxyquinoline N-oxide 8-hydroxyquinoline N-oxide : A quinoline N-oxide carrying a hydroxy substituent at position 8.	2.06	1	0	monohydroxyquinoline; quinoline N-oxide
dihydroferulic acid dihydroferulic acid: structure in first source. dihydroferulic acid : A monocarboxylic acid that is propanoic acid in which one of the hydrogens at position 3 has been replaced by a 4-hydroxy-3-methoxyphenyl group.	2.13	1	0	guaiacols; monocarboxylic acid; phenylpropanoid	antioxidant; human xenobiotic metabolite; mouse metabolite; plant metabolite
lauryl gallate [no description available]	2.01	1	0	gallate ester
carmine Carmine: Coloring matter from the insect Coccus cacti L. It is used in foods, pharmaceuticals, toiletries, etc., as a dye, and also has use as a microscopic stain and biological marker.	5.09	1	1
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).	2.21	1	0
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.	10.4	3	1	zinc molecular entity
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.	3.73	10	0	alpha-tocopherol	algal metabolite; antiatherogenic agent; anticoagulant; antioxidant; antiviral agent; EC 2.7.11.13 (protein kinase C) inhibitor; immunomodulator; micronutrient; nutraceutical; plant metabolite
3,5-di-tert-butyl-4-hydroxybenzoic acid [no description available]	2.07	1	0
2,6-dimethoxybenzoic acid 2,6-dimethoxybenzoic acid: structure in first source	2.48	2	0	benzenes; carbonyl compound
clopyralid clopyralid : An organochlorine pesticide having a 3,6-dichlorinated picolinic acid structure.	2.06	1	0	organochlorine pesticide; pyridines	herbicide
orange g orange G : An organic sodium salt that is the disodium salt of 7-hydroxy-8-[(E)-phenyldiazenyl]naphthalene-1,3-disulfonic acid. It is often combined with other yellow dyes in alcoholic solution to stain erythrocytes in trichrome methods, and is used for demonstrating cells in the pancreas and pituitary.	2.21	1	0
diallyl trisulfide [no description available]	2.04	1	0	organic trisulfide	anti-inflammatory agent; antilipemic drug; antineoplastic agent; antioxidant; antiprotozoal drug; apoptosis inducer; estrogen receptor antagonist; insecticide; platelet aggregation inhibitor; vasodilator agent
4-chlorocatechol 4-chlorocatechol : A chlorocatechol that is catechol substituted by a chloro group at position 4.	7.35	2	0	chlorocatechol; monochlorobenzenes	bacterial xenobiotic metabolite
diallyl disulfide diallyl disulfide: major constituent of garlic oil. diallyl disulfide : An organic disulfide where the organic group specified is allyl. It has been isolated from garlic and other species of the genus Allium.	2.42	2	0	organic disulfide	antifungal agent; antineoplastic agent; plant metabolite
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.	2.11	1	0	isothiocyanate	antineoplastic agent; EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor; metabolite
acetosyringone acetosyringone: plant inducer which induces expression of VirE & VirG in A. tumefaciens. acetosyringone : A member of the class of acetophenones that is 1-phenylethanone substituted by a hydroxy group at position 4 and methoxy groups at positions 3 and 5.	2.02	1	0	acetophenones; dimethoxybenzene; phenols	anti-asthmatic drug; non-narcotic analgesic; non-steroidal anti-inflammatory drug; peripheral nervous system drug; plant metabolite
2-(2-hydroxyphenyl)benzothiazole 2-(1,3-benzothiazol-2-yl)phenol : A member of the class of benzothiazoles that is 1,3-benzothiazole substituted by a 2-hydroxyphenyl group at position 2.	2.06	1	0	benzothiazoles; phenols	geroprotector
4,5-dichlorocatechol [no description available]	2.13	1	0
dithiothreitol 1,4-dimercaptobutane-2,3-diol : A glycol that is butane-2,3-diol in which a hydrogen from each of the methyl groups is replaced by a thiol group.. 1,4-dithiothreitol : The threo-diastereomer of 1,4-dimercaptobutane-2,3-diol.	5.09	1	1	1,4-dimercaptobutane-2,3-diol; butanediols; dithiol; glycol; thiol	chelator; human metabolite; reducing agent
acedoben 4-acetamidobenzoic acid : A amidobenzoic acid that consists of benzoic acid bearing an acetamido substituent at position 4.	2.05	1	0	amidobenzoic acid
3-phenoxybenzoic acid 3-phenoxybenzoic acid: metabolite associated with exposure to pyrethroid insecticides. 3-phenoxybenzoic acid : A phenoxybenzoic acid in which the phenoxy group is meta to the carboxy group. It is a metabolite of pyrethroid insecticides.	2.52	2	0	phenoxybenzoic acid	human xenobiotic metabolite; marine xenobiotic metabolite
butylhydroxybutylnitrosamine Butylhydroxybutylnitrosamine: A substituted carcinogenic nitrosamine.. N-butyl-N-(4-hydroxybutyl)nitrosamine : A nitrosamine that has butyl and 4-hydroxybutyl substituents. In mice, it causes high-grade, invasive cancers in the urinary bladder, but not in any other tissues.	1.98	1	0	nitrosamine; primary alcohol	carcinogenic agent
3-o-methylgallic acid 3-O-methylgallic acid: structure in first source. 3-O-methylgallic acid : A member of the class of benzoic acids that is gallic acid in which the phenolic hydroxy group at position 3 is converted into the corresponding methyl ether.	1.97	1	0	benzoic acids; catechols
methyl vanillate methyl vanillate: isolated from Hovenia dulcis. methyl vanillate : A benzoate ester that is the methyl ester of vanillic acid.	2.01	1	0	aromatic ether; benzoate ester; phenols	antioxidant; plant metabolite
3-chlorocatechol 3-chlorocatechol: inhibits catechol-2,3-dioxygenase. chlorocatechol : Any member of the class of catechols that is catechol substituted by at least one chloro group.. 3-chlorocatechol : A chlorocatechol that is catechol in which the hydrogen adjacent to one of the hydroxy groups is replaced by a chlorine.	2.02	1	0	chlorocatechol; monochlorobenzenes
ethyl maltol ethyl maltol: structure given in first source	2.06	1	0	pyranone
2-aminobenzyl alcohol 2-aminobenzyl alcohol: structure given in first source	2.15	1	0
iridium Iridium: A metallic element with the atomic symbol Ir, atomic number 77, and atomic weight 192.22.	5.09	1	1	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.	7.05	1	0	elemental manganese; manganese group element atom	Escherichia coli metabolite; micronutrient
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.	5.09	1	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.	2.54	2	0	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.	2.82	3	0	cadmium molecular entity; zinc group element atom
europium Europium: An element of the rare earth family of metals. It has the atomic symbol Eu, atomic number 63, and atomic weight 152. Europium is used in the form of its salts as coatings for cathode ray tubes and in the form of its organic derivatives as shift reagents in NMR spectroscopy.	5.09	1	1	f-block element atom; lanthanoid atom
gadolinium Gadolinium: An element of the rare earth family of metals. It has the atomic symbol Gd, atomic number 64, and atomic weight 157.25. Its oxide is used in the control rods of some nuclear reactors.	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.	10.54	4	1	copper group element atom; elemental gold
yttrium Yttrium: An element of the rare earth family of metals. It has the atomic symbol Y, atomic number 39, and atomic weight 88.91. In conjunction with other rare earths, yttrium is used as a phosphor in television receivers and is a component of the yttrium-aluminum garnet (YAG) lasers.	2.02	1	0	d-block element atom; rare earth metal atom; scandium group element atom
galactosamine 2-amino-2-deoxy-D-galactopyranose : The pyranose form of D-galactosamine.. D-galactosamine : The D-stereoisomer of galactosamine.	7.13	1	0	D-galactosamine; primary amino compound	toxin
sodium nitrate sodium nitrate : The inorganic nitrate salt of sodium.	2.07	1	0	inorganic nitrate salt; inorganic sodium salt	fertilizer; NMR chemical shift reference compound
hypochlorous acid Hypochlorous Acid: An oxyacid of chlorine (HClO) containing monovalent chlorine that acts as an oxidizing or reducing agent.. hypochlorous acid : A chlorine oxoacid with formula HOCl; a weak, unstable acid, it is the active form of chlorine in water.	2.07	1	0	chlorine oxoacid; reactive oxygen species	EC 2.5.1.18 (glutathione transferase) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; human metabolite
ferrous chloride ferrous chloride: induces convulsions; RN given refers to parent cpd	2.03	1	0	iron coordination entity
copper sulfate Copper Sulfate: A sulfate salt of copper. It is a potent emetic and is used as an antidote for poisoning by phosphorus. It also can be used to prevent the growth of algae.. copper(II) sulfate : A metal sulfate compound having copper(2+) as the metal ion.	4.62	4	0	metal sulfate	emetic; fertilizer; sensitiser
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
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.	2.54	2	0	titanium oxides	food colouring
3,5-dichlorocatechol 3,5-dichlorocatechol : A dichlorocatechol carrying chloro groups at positions 3 and 5.	2.02	1	0	dichlorocatechol
selegiline Selegiline: A selective, irreversible inhibitor of Type B monoamine oxidase that is used for the treatment of newly diagnosed patients with PARKINSON DISEASE, and for the treatment of depressive disorders. The compound without isomeric designation is Deprenyl.	2	1	0	selegiline; terminal acetylenic compound	geroprotector
ferric nitrilotriacetate ferric nitrilotriacetate: induces diabetes in animals (iron loading)	2.01	1	0	iron chelate	carcinogenic agent; mutagen
tetradecanoylphorbol acetate Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.	3.27	6	0	acetate ester; diester; phorbol ester; tertiary alpha-hydroxy ketone; tetradecanoate ester	antineoplastic agent; apoptosis inducer; carcinogenic agent; mitogen; plant metabolite; protein kinase C agonist; reactive oxygen species generator
2,3-dihydroxypyridine 2,3-dihydroxypyridine: affects thyroid function. pyridine-2,3-diol : A dihydroxypyridine in which the two hydroxy groups are located at positions 2 and 3.	2.06	1	0	dihydroxypyridine
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.	2.46	2	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.	2.08	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
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.	2.01	1	0	aminoglycoside antibiotic; anthracycline; p-quinones; tetracenequinones	antineoplastic agent; bacterial metabolite
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
4-anisaldehyde 4-anisaldehyde: RN given refers to cpd with specified locants for methoxy moieties; structure in Merck, 9th ed, #696. p-methoxybenzaldehyde : A member of the class of benzaldehydes consisting of benzaldehyde itself carrying a methoxy substituent at position 4.	2.46	2	0	benzaldehydes	bacterial metabolite; human urinary metabolite; insect repellent; plant metabolite
acetylacetone acetylacetone : A beta-diketone that is pentane in which the hydrogens at positions 2 and 4 are replaced by oxo groups.	2.06	1	0	beta-diketone
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.	3.86	3	0	phenols	antioxidant; ferroptosis inhibitor; food additive; geroprotector
pyrene pyrene: structure in Merck Index, 9th ed, #7746. pyrene : An ortho- and peri-fused polycyclic arene consisting of four fused benzene rings, resulting in a flat aromatic system.	2.6	1	0	ortho- and peri-fused polycyclic arene	fluorescent probe; persistent organic pollutant
silybin silibinin : A flavonolignan isolated from milk thistle, Silybum marianum, that has been shown to exhibit antioxidant and antineoplastic activities.	2.05	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.	2.46	2	0
alkenes [no description available]	2.15	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.	3.59	2	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.	7.67	3	0
ferrozine Ferrozine: A ferroin compound that forms a stable magenta-colored solution with the ferrous ion. The complex has an absorption peak at 562 nm and is used as a reagent and indicator for iron.	2.03	1	0
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).	2.15	1	0	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
3-phenoxybenzaldehyde [no description available]	2.17	1	0
1-methyl-4-phenylpyridinium 1-Methyl-4-phenylpyridinium: An active neurotoxic metabolite of 1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE. The compound reduces dopamine levels, inhibits the biosynthesis of catecholamines, depletes cardiac norepinephrine and inactivates tyrosine hydroxylase. These and other toxic effects lead to cessation of oxidative phosphorylation, ATP depletion, and cell death. The compound, which is related to PARAQUAT, has also been used as an herbicide.. N-methyl-4-phenylpyridinium : A pyridinium ion that is N-methylpyridinium having a phenyl substituent at the 4-position.	2.71	3	0	pyridinium ion	apoptosis inducer; herbicide; human xenobiotic metabolite; neurotoxin
ng-nitroarginine methyl ester NG-Nitroarginine Methyl Ester: A non-selective inhibitor of nitric oxide synthase. It has been used experimentally to induce hypertension.	2.08	1	0	alpha-amino acid ester; L-arginine derivative; methyl ester; N-nitro compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid [no description available]	4.43	6	0	chromanol; monocarboxylic acid; phenols	antioxidant; ferroptosis inhibitor; neuroprotective agent; radical scavenger; Wnt signalling inhibitor
acarbose [no description available]	2.85	3	0	tetrasaccharide derivative	EC 3.2.1.1 (alpha-amylase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; geroprotector; hypoglycemic agent
piperacillin Piperacillin: Semisynthetic, broad-spectrum, AMPICILLIN derived ureidopenicillin antibiotic proposed for PSEUDOMONAS infections. It is also used in combination with other antibiotics.. piperacillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-[(4-ethyl-2,3-dioxopiperazin-1-yl)carboxamido]-2-phenylacetamido group.	2.05	1	0	penicillin allergen; penicillin	antibacterial drug
4-(n-methyl-n-nitrosamino)-1-(3-pyridyl)-1-butanone 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone: structure; from tobacco smoke	2	1	0	nitrosamine; pyridines
2-amino-3-methylimidazo(4,5-f)quinoline 2-amino-3-methylimidazo(4,5-f)quinoline: mutagen found in broiled food; RN given refers to parent cpd; structure given in first source; frequently abbreviated as IQ in the literature. 3-methyl-3H-imidazo[4,5-f]quinolin-2-amine : An imidazoquinoline that is 3H-imidazo[4,5-f]quinoline substituted by a methyl group at position 3 and an amino group at position 2.	2.31	1	0	imidazoquinoline	carcinogenic agent
esmolol methyl 3-{4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl}propanoate : A methyl ester that is methyl 3-(4-hydroxyphenyl)propanoate in which the hydrogen attached to the phenolic hydroxy group is substituted by a 2-hydroxy-3-(isopropylamino)propyl group.. esmolol : A racemate comprising equimolar amounts of (R)- and (S)-esmolol. A cardioselective and short-acting beta1 receptor blocker with rapid onset but lacking intrinsic sympathomimetic and membrane-stabilising properties, it is used as the hydrochloride salt in the management of supraventricular arrhythmias, and for the control of hypertension and tachycardia during surgery. While the S enantiomer possesses all of the heart rate control, both enantiomers contribute to lowering blood pressure.	5.09	1	1	aromatic ether; ethanolamines; methyl ester; secondary alcohol; secondary amino compound
adenosine quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit	2.08	1	0	adenosines; purines D-ribonucleoside	analgesic; anti-arrhythmia drug; fundamental metabolite; human metabolite; vasodilator agent
octyl gallate [no description available]	2.01	1	0	gallate ester	food antioxidant; hypoglycemic agent; plant metabolite
vanillyl alcohol vanillyl alcohol: structure. vanillyl alcohol : A monomethoxybenzene that is 2-methoxyphenol substituted by a hydroxymethyl group at position 4.	2.02	1	0	benzyl alcohols; guaiacols	plant metabolite
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.	6.12	44	0	D-glucopyranose	epitope; mouse metabolite
ursolic acid [no description available]	3.25	1	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	geroprotector; plant metabolite
betulinic acid [no description available]	3.91	3	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	anti-HIV agent; anti-inflammatory agent; antimalarial; antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; plant metabolite
baicalin [no description available]	2.49	2	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.	2.08	1	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
thionine thionine: do not confuse with the thionins which is a class of polypeptides; RN above is for the chloride;. thionine : An organic chloride salt composed of 3,7-diaminophenothiazin-5-ium and chloride ions in a 1:1 ratio. A strongly metachromatic dye, useful for the staining of acid mucopolysaccharides. It is also a common nuclear stain and can be used for the demonstration of Nissl substance in nerve cells of the CNS.	2.02	1	0
4-hydroxybenzamide [no description available]	2.15	1	0
epigallocatechin gallate epigallocatechin gallate: a steroid 5alpha-reductase inhibitor and antimutagen in green tea (Camellia sinensis). (-)-epigallocatechin 3-gallate : A gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (-)-epigallocatechin.	2.98	4	0	flavans; gallate ester; polyphenol	antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite
alpha-terthienyl [no description available]	2.06	1	0	terthiophene
3-amino-4-hydroxybenzoic acid 3-amino-4-hydroxybenzoic acid : A monohydroxybenzoic acid that is 4-hydroxybenzoic acid carrying an additional amino substitutent at position 3.	2.03	1	0	aminobenzoic acid; monohydroxybenzoic acid
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.	2.58	2	0	gallocatechin	antioxidant; metabolite; radical scavenger
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.	2.8	3	0	gallate ester; galloyl beta-D-glucose	anti-inflammatory agent; antineoplastic agent; geroprotector; hepatoprotective agent; plant metabolite; radiation protective agent; radical scavenger
glutathione disulfide Glutathione Disulfide: A GLUTATHIONE dimer formed by a disulfide bond between the cysteine sulfhydryl side chains during the course of being oxidized.	1.98	1	0	glutathione derivative; organic disulfide	Escherichia coli metabolite; mouse metabolite
bergenin bergenin: RN refers to (2R-(2alpha,3beta,4alpha,4aalpha,10bbeta))-isomer; structure	2.08	1	0	trihydroxybenzoic acid	metabolite
2,4,6-trihydroxybenzoic acid [no description available]	3.65	2	0	hydroxybenzoic acid
1,2,4-trimethoxybenzene 1,2,4-trimethoxybenzene: a volatile organic compound	2.48	2	0	methoxybenzenes
1,7-phenanthroline [no description available]	2.41	2	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.	5.09	1	1	1,2,3-triazole
5-fluorosalicylic acid 5-fluorosalicylic acid: structure given in first source; product from action of alkaline phosphatase on 5-fluorosalicyl phosphate; forms highly fluorescent terbium ternary complex	2.06	1	0
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.	3.25	1	0	(2S)-flavan-4-one; dihydroxyflavanone	antineoplastic agent; antioxidant; metabolite; neuroprotective agent; vasodilator agent
2,4,6-trihydroxybenzaldehyde 2,4,6-trihydroxybenzaldehyde: structure in first source	2.52	2	0	carboxylic ester
isocoumarins Isocoumarins: Compounds that differ from COUMARINS in having the positions of the ring and ketone oxygens reversed so the keto oxygen is at the 1-position of the molecule.. isocoumarin : The simplest member of the class of isocoumarins that is 1H-isochromene which is substituted by an oxo group at position 1.	2.13	1	0	isocoumarins
pyromeconic acid pyromeconic acid: from herb Dengzhanhua; structure	2.06	1	0
sesamol sesamol: constituent of sesame oil; RN given refers to parent cpd; structure in first source	2.25	1	0	benzodioxoles
2-hydroxypyrimidine pyrimidone : A pyrimidine carrying one or more oxo substituents.. pyrimidin-2-ol : The hydroxypyrimidine that is pyrimidine mono-substituted at C-2 by a hydroxy group.	2.06	1	0	hydroxypyrimidine	electron donor; Lewis base
1-octacosanol 1-octacosanol: RN given refers to parent cpd. octacosan-1-ol : An ultra-long-chain primary fatty alcohol that is octacosane in which a hydrogen attached to one of the terminal carbons is replaced by a hydroxy group.	2.07	1	0	fatty alcohol 28:0; ultra-long-chain primary fatty alcohol	plant metabolite
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.	2.17	1	0	organic peroxide; sesquiterpene lactone	antimalarial; plant metabolite
2-hydroxynicotinic acid [no description available]	2.15	1	0	aromatic carboxylic acid; pyridines
4-aminobenzyl alcohol 4-aminobenzyl alcohol: structure	2.15	1	0
allomaltol allomaltol: structure in first source	2.06	1	0
2-hydroxy-4-methoxybenzaldehyde 2-hydroxy-4-methoxybenzaldehyde: from African medicinal plants: Mondia whitei (Apocynaceae), Rhus vulagaris (Anacardiaceae), Sclerocarya caffra (Anacardiaceae)	2.03	1	0	methoxybenzenes; phenols
indole-3-carboxylic acid indole-3-carboxylic acid : An indole-3-carboxylic acid carrying a carboxy group at position 3.	2.13	1	0	indol-3-yl carboxylic acid	bacterial metabolite; human metabolite
1-hydroxy-2(1h)-pyridinone 1-hydroxy-2(1H)-pyridinone: structure in first source	2.06	1	0
2,5-dihydroxybenzaldehyde 2,5-dihydroxybenzaldehyde: structure in first source. 2,5-dihydroxybenzaldehyde : A dihydroxybenzaldehyde carrying hydroxy groups at positions 2 and 5.	2.03	1	0	dihydroxybenzaldehyde	human metabolite; mouse metabolite; Penicillium metabolite
epicatechin (-)-epicatechin : A catechin with (2R,3R)-configuration.	3.32	6	0	catechin; polyphenol	antioxidant
gallocatechol (-)-epigallocatechin : A flavan-3,3',4',5,5',7-hexol having (2R,3R)-configuration.	2.47	2	0	catechin; flavan-3,3',4',5,5',7-hexol	antioxidant; food component; plant metabolite
6-hydroxyflavone 6-hydroxyflavone: antioxidant; structure in first source	2.21	1	0	hydroxyflavonoid
tetrahydropalmatine [no description available]	2.07	1	0	an (S)-7,8,13,14-tetrahydroprotoberberine; berberine alkaloid; organic heterotetracyclic compound	adrenergic agent; dopaminergic antagonist; non-narcotic analgesic
sesamin (+)-sesamin : A lignan that consists of tetrahydro-1H,3H-furo[3,4-c]furan substituted by 1,3-benzodioxole groups at positions 1 and 4 (the 1S,3aR,4S,6aR stereoisomer). Isolated from Cinnamomum camphora, it exhibits cytotoxic activity.	2.25	1	0	benzodioxoles; furofuran; lignan	antineoplastic agent; neuroprotective agent; plant metabolite
betulin betulin: isolated from various white birch bark (BETULA). betulin : A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-hydroxymethyl substituents.	2.08	1	0	diol; pentacyclic triterpenoid	analgesic; anti-inflammatory agent; antineoplastic agent; antiviral agent; metabolite
5-iminodaunorubicin 5-iminodaunorubicin: RN given refers to parent cpd	2.01	1	0
alantolactone alantolactone: allergenic sesquiterpene lactone; crystalline mixture of alantolactones from group of sesquiterpenes; structure. alantolactone : A sesquiterpene lactone that is 3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2-one bearing two methyl substituents at positions 5 and 8a as well as a methylidene substituent at position 3.	2.07	1	0	naphthofuran; olefinic compound; sesquiterpene lactone	antineoplastic agent; apoptosis inducer; plant metabolite
6-hydroxynicotinic acid 6-hydroxynicotinic acid : A monohydroxypyridine that is the 6-hydroxy derivative of nicotinic acid.	2	1	0	monohydroxypyridine	Arabidopsis thaliana metabolite; human urinary metabolite; mouse metabolite
kaurenoic acid [no description available]	2.17	1	0	ent-kaurane diterpenoid	anti-HIV-1 agent; antineoplastic agent; plant metabolite
(-)-catechin (-)-catechin : The (-)-enantiomer of catechin.	2.49	2	0	catechin	metabolite
isoalantolactone isoalantolactone: RN given refers to (3aR-(3aalpha,4aalpha,8abeta,9aalpha))-isomer; structure. isoalantolactone : A sesquiterpene lactone of the eudesmanolide group. It has been isolated from Inula helenium.	2.07	1	0	eudesmane sesquiterpenoid; sesquiterpene lactone	antifungal agent; apoptosis inducer; plant metabolite
pinoresinol (+)-pinoresinol : An enantiomer of pinoresinol having (+)-1S,3aR,4S,6aR-configuration.	2.15	1	0	pinoresinol	hypoglycemic agent; phytoestrogen; plant metabolite
corilagin corilagin: isolated from Geranii herba. corilagin : An ellagitannin with a hexahydroxydiphenoyl group bridging over the 3-O and 6-O of the glucose core.	2.06	1	0	ellagitannin; gallate ester	antihypertensive agent; antioxidant; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; non-steroidal anti-inflammatory drug
1-aminoisoquinoline [no description available]	2.13	1	0
2,2'-dipicolylamine 2,2'-dipicolylamine: structure in first source	2.06	1	0
8-hydroxy-2-quinolinecarboxylic acid [no description available]	2.06	1	0	quinolines
fluoren-9-ol fluoren-9-ol : A member of the class of hydroxyfluorenes that is 9H-fluorene substituted by a hydroxy group at position 9 (the non-aromatic carbon).	2	1	0	hydroxyfluorenes; secondary alcohol	animal metabolite
3-chloro-2,4-pentanedione 3-chloro-2,4-pentanedione: structure in first source	2.06	1	0
3-(3,4-dimethoxyphenyl)propanoic acid 3-(3,4-dimethoxyphenyl)propanoic acid : A monocarboxylic acid that is propanoic acid substituted by a 3,4-dimethoxyphenyl group at position 3.	2.11	1	0	dimethoxybenzene; monocarboxylic acid
methyl gentisate methyl gentisate: skin lightening agent; structure in first source	2.08	1	0	benzoate ester; phenols
4-carboxybiphenyl ether 4-carboxybiphenyl ether: structure given in first source. 4-phenoxybenzoic acid : A phenoxybenzoic acid in which the phenoxy group is para to the carboxy group.	1.97	1	0	phenoxybenzoic acid
ethyl protocatechuate ethyl protocatechuate: structure. ethyl 3,4-dihydroxybenzoate : An ethyl ester resulting from the formal condensation of the carboxy group of 3,4-dihydroxybenzoic acid with ethanol. It is the anti-oxidative component of peanut seed testa.	8.04	4	0	catechols; ethyl ester	antibacterial agent; antioxidant; apoptosis inducer; EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor; plant metabolite
3,5-dihydroxy-4-methoxybenzoic acid 3,5-dihydroxy-4-methoxybenzoic acid: catechol methyltransferase inhibitor; N1 same as NM	2.47	2	0	trihydroxybenzoic acid
nonyl gallate [no description available]	2.01	1	0
3,4-dihydroxyphenylethanol 3,4-dihydroxyphenylethanol: serotonin metabolite; structure	2.72	3	0	catechols; primary alcohol	antineoplastic agent; antioxidant; metabolite
clarithromycin Clarithromycin: A semisynthetic macrolide antibiotic derived from ERYTHROMYCIN that is active against a variety of microorganisms. It can inhibit PROTEIN SYNTHESIS in BACTERIA by reversibly binding to the 50S ribosomal subunits. This inhibits the translocation of aminoacyl transfer-RNA and prevents peptide chain elongation.. clarithromycin : The 6-O-methyl ether of erythromycin A, clarithromycin is a macrolide antibiotic used in the treatment of respiratory-tract, skin and soft-tissue infections. It is also used to eradicate Helicobacter pylori in the treatment of peptic ulcer disease. It prevents bacteria from growing by interfering with their protein synthesis.	2.04	1	0	macrolide antibiotic	antibacterial drug; environmental contaminant; protein synthesis inhibitor; xenobiotic
5-amino-1,3,4-thiadiazole-2-sulfonamide 5-amino-1,3,4-thiadiazole-2-sulfonamide: structure in first source	2.06	1	0
3,4-dihydroxymandelic acid 3,4-dihydroxymandelic acid: metabolite of L-dopa; RN given refers to parent cpd without isomeric designation. 3,4-dihydroxymandelic acid : A catechol that is the 3,4-dihydroxy derivative of mandelic acid; a metabolite of L-dopa.	2.37	2	0	2-hydroxy monocarboxylic acid; catechols	antioxidant; drug metabolite; human metabolite; mouse metabolite
1-methyl-2-ethyl-3-hydroxypyridin-4-one [no description available]	2.06	1	0
cp094 1,2-diethyl-3-hydroxypyridin-4-one: structure given in first source	2.06	1	0
coenzyme a [no description available]	2.55	2	0	adenosine 3',5'-bisphosphate	coenzyme; Escherichia coli metabolite; mouse metabolite
1-methyl-3-hydroxypyridine-2-one [no description available]	2.06	1	0
9,10-dihydroxystearic acid 9,10-dihydroxyoctadecanoic acid : A hydroxy-fatty acid formally derived from octacecanoic (stearic) acid by hydroxy substitution at positions 9 and 10.	2.25	1	0	dihydroxy monocarboxylic acid; hydroxyoctadecanoic acid
aucubin [no description available]	2.07	1	0	organic molecular entity	metabolite
friedelin 3-friedelanone: from the stem bark of Irvingia gabonensis; structure in first source. friedelin : A pentacyclic triterpenoid that is perhydropicene which is substituted by an oxo group at position 3 and by methyl groups at the 4, 4a, 6b, 8a, 11, 11, 12b, and 14a-positions (the 4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS-enantiomer). It is the major triterpenoid constituent of cork.	2.02	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
3,4-dihydroxyphenylglycol 3,4-dihydroxyphenylglycol: noradrenaline metabolite in mouse brain; RN given refers to cpd without isomeric designation. 3,4-dihydroxyphenylethyleneglycol : A tetrol composed of ethyleneglycol having a 3,4-dihydroxyphenyl group at the 1-position.	2.13	1	0	catechols; tetrol	metabolite; mouse 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.	2.42	2	0	amino acid zwitterion; homocysteine; serine family amino acid	fundamental metabolite; mouse metabolite
2-amino-5-chlorophenol 2-amino-5-chlorophenol: structure given in first source. 2-amino-5-chlorophenol : Phenol carrying amino and chloro substituents at positions 2 and 5 respectively. It is part of the degradation pathway of 4-chloronitrobenzene, CHEBI:34399.	2.02	1	0	monochlorobenzenes; phenols; primary amino compound
fosthiazate fosthiazate: structure in first source	2.07	1	0	organic phosphonate; organothiophosphate insecticide; phosphonic ester	agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor; nematicide
taraxerol taraxerol: structure. taraxerol : A pentacyclic triterpenoid that is oleanan-3-ol lacking the methyl group at position 14, with an alpha-methyl substituent at position 13 and a double bond between positions 14 and 15.	2.21	1	0	pentacyclic triterpenoid; secondary alcohol	metabolite
picein picein: RN given refers to (beta-D)-isomer	2.11	1	0	glycoside
succinyl-coenzyme a [no description available]	2.42	2	0	omega-carboxyacyl-CoA	Escherichia coli metabolite; inhibitor; mouse metabolite
taraxerone taraxerone: structure	2.21	1	0	scalarane sesterterpenoid	metabolite
beta-hydroxyphenylpropionic acid beta-hydroxyphenylpropionic acid: benzoic acid metabolite in urine. 3-hydroxy-3-phenylpropionic acid : A 3-hydroxy carboxylic acid that is 3-phenylpropionic acid in which one of the hydrogens beta to the carboxy group is replaced by a hydroxy group.	2.07	1	0	3-hydroxy carboxylic acid; monocarboxylic acid
glycidyl nitrate glycidyl nitrate: a nitric oxide donor; structure in first source. peptidoglycan : A peptidoglycosaminoglycan formed by alternating residues of beta-(1->4)-linked N-acetylglucosamine and N-acetylmuramic acid {2-amino-3-O-[(S)-1-carboxyethyl]-2-deoxy-D-glucose} residues. Attached to the carboxy group of the muramic acid is a peptide chain of three to five amino acids.	2.07	1	0
1-ethyl-2-methyl-3-hydroxypyridin-4-one [no description available]	2.06	1	0
2-acetylcyclopentanone 2-acetylcyclopentanone: an enolate-forming compound that is protective against electrophilic drugs; structure in first source	2.06	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	2.08	1	0	glycoside; lignan
sesamolin sesamolin: constituent of sesame oil; RN given refers to the (1S-(1alpha,3aalpha,4alpha,6aalpha)-isomer); inhibits proliferation of human lymphocytic leukemia cells in culture	2.25	1	0	benzodioxoles
n-methyladenosine N-methyladenosine: is a inhibitor of cell differentiation. N(6)-methyladenosine : A methyladenosine compound with one methyl group attached to N(6) of the adenine nucleobase.	5.09	1	1	methyladenosine
octaethylporphyrin octaethylporphyrin: structure in first source	2.02	1	0
cobalt Cobalt: A trace element that is a component of vitamin B12. It has the atomic symbol Co, atomic number 27, and atomic weight 58.93. It is used in nuclear weapons, alloys, and pigments. Deficiency in animals leads to anemia; its excess in humans can lead to erythrocytosis.. cobalt(1+) : A monovalent inorganic cation obtained from cobalt.. cobalt atom : A cobalt group element atom that has atomic number 27.	4.04	4	0	cobalt group element atom; metal allergen	micronutrient
geniposide [no description available]	2.03	1	0	terpene glycoside
procyanidin Proanthocyanidins: Dimers and oligomers of flavan-3-ol units (CATECHIN analogs) linked mainly through C4 to C8 bonds to leucoanthocyanidins. They are structurally similar to ANTHOCYANINS but are the result of a different fork in biosynthetic pathways.	4.55	6	0	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.	2.05	1	0	catechin; gallate ester; polyphenol	EC 3.2.1.1 (alpha-amylase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; metabolite
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).	2.04	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.	2.39	2	0	octadecatetraenoic acid
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
aristolochic acid ii aristolochic acid II: structure given in first source. aristolochic acid B : An aristolochic acid that is phenanthrene-1-carboxylic acid substituted by a methylenedioxy group at the 3,4 positions and by a nitro group at position 10.	2.15	1	0	aristolochic acids; aromatic ether; C-nitro compound; cyclic acetal; monocarboxylic acid; organic heterotetracyclic compound	carcinogenic agent; metabolite; mutagen; nephrotoxin; toxin
exp3174 losartan carboxylic acid: structure given in first source. losartan carboxylic acid : A biphenylyltetrazole that is losartan with the hydroxymethyl group at position 5 on the imidazole ring replaced with a carboxylic acid.	2.07	1	0	biphenylyltetrazole; imidazoles; organochlorine compound	metabolite
homoorientin homoorientin: isolated from Swertia japonica; structure given in first source	2.45	2	0	flavone C-glycoside; tetrahydroxyflavone	antineoplastic agent; radical scavenger
tanshinone tanshinone: from root of Salvia miltiorrhiza Bunge; RN given refers to tanshinone I; cardioprotective agent and neuroprotective agent	2.93	4	0	abietane diterpenoid	anticoronaviral agent
gastrodin gastrodin: the glucoside of 4-hydroxybenzyl alcohol (gastrodigenin); isolated from Gastrodia elata Blume;	2.04	1	0	glycoside
ponasterone a ponasterone A: RN given refers to (2 beta,3 beta,5 beta,22R)-isomer	2.15	1	0	14alpha-hydroxy steroid; 20-hydroxy steroid; 22-hydroxy steroid; 2beta-hydroxy steroid; 3beta-hydroxy steroid; 6-oxo steroid; phytoecdysteroid
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).	2.15	1	0	gamma-lactone; lignan; polyphenol	angiogenesis inhibitor; anti-asthmatic agent; phytoestrogen; plant metabolite
aristolic acid aristolic acid: this is aristolochic acid without the nitro group	2.15	1	0
aspidin bb [no description available]	3.25	1	0
benzoyl-coenzyme a benzoyl-coenzyme A: RN given refers to unlabeled cpd	2.97	4	0
saccharolactone saccharolactone: used as index for assessing induction of hepatic enzymes by anticonvulsants; RN given refers to cpd without isomeric designation. D-glucaro-1,4-lactone : A delta-lactone that is D-glucono-1,4-lactone in which the hydroxy group at position 6 has been oxidised to the corresponding carboxylic acid.	2.06	1	0	aldarolactone; delta-lactone
astragaloside a [no description available]	2.15	1	0
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.	2.66	2	0	biflavonoid; hydroxyflavan; polyphenol; proanthocyanidin	antioxidant; metabolite
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.	2.78	3	0	4'-hydroxyflavanones; dihydroflavonols; secondary alpha-hydroxy ketone; tetrahydroxyflavanone	metabolite
3-hydroxydiploptene 3-hydroxydiploptene: biosynthesized from squalene or epoxy dihydrosqualene in cell-free system from Methylococcus capsulatus; RN given refers to (3beta)-isomer	2.07	1	0
methotrexate [no description available]	7.21	1	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
dihydroethidium dihydroethidium: RN given is for the (+-)-isomer	2.01	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.	3.95	3	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.	5.96	12	0	5-hydroxyanthocyanidin	antioxidant; metabolite; neuroprotective agent
xylose xylopyranose: structure in first source	2.72	2	0	D-xylose
4-amino-3-hydroxybenzoic acid [no description available]	2.03	1	0
4-propylbenzoic acid [no description available]	2.03	1	0	alkylbenzene
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.	3.31	1	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
8-(methylsulfonylamino)quinoline 8-(methylsulfonylamino)quinoline: has diabetogenic properties; structure given in first source	2.06	1	0
10-deacetyltaxol 10-deacetyltaxol: alkaloid from Taxus wallichiana, structure given in first source	2.15	1	0
hydroxyl radical Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.	8.35	16	1	oxygen hydride; oxygen radical; reactive oxygen species
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'.	2.13	1	0	5-hydroxyanthocyanidin	biological pigment; metabolite
cryptotanshinone cryptotanshinone: from Salvia miltiorrhiza	2.83	3	0	abietane diterpenoid	anticoronaviral agent
fenton's reagent Fenton's reagent: used for oxidizing sugars & alcohols	2.73	3	0
carbodiimides Carbodiimides: Compounds with the general formula RN=C=NR, where R is a hydrocarbyl group.. methanediimine : A carbodiimide in which both nitrogens are unsubstituted.	2.13	1	0	carbodiimide
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.	2.44	2	0	guaiacols; lignan; polyphenol; primary alcohol	plant metabolite
3-hydroxystigmast-5-en-7-one [no description available]	2.15	1	0	steroid
aminoimidazole ribotide 5-amino-1-(5-phospho-beta-D-ribosyl)imidazole : A 1-(phosphoribosyl)imidazole that is 5-aminoimidazole in which the proton at position 1 has been replaced by a 5-phospho-beta-D-ribofuranosyl group.	2.13	1	0	1-(phosphoribosyl)imidazole; aminoimidazole	bacterial metabolite
syringopicroside syringopicroside: from leaves of Syringa oblata Lindl.; structure given in first source	1.96	1	0
1-(2,6-dimethylphenoxy)-2-(3,4-dimethoxyphenylethylamino)propane [no description available]	2.13	1	0
methylinositol methylinositol: from Ebenus haussknechtii; structure in first source. pinitol : A cyclitol ether formed by etherification of the 3-hydroxy group of chiro-inositol. It is plant metabolite isolated from the leaves of Sutherlandia frutescens.. 1D-4-O-methyl-myo-inositol : A member of the class of methyl myo-inositols that is cyclohexane-1,2,3,4,5-pentol substituted by a methoxy group at position 6 (the 1R,2S,3S,4S,5S,6S-isomer).. D-pinitol : The D-enantiomer of pinitol.	3.25	1	0
3,4-dihydroxybenzophenone 3,4-dihydroxybenzophenone: structure in first source	2.08	1	0
(22r)-22-hydroxycholesterol (22R)-22-hydroxycholesterol : An oxysterol that is the 22R-hydroxy derivative of cholesterol.	2.08	1	0	22-hydroxy steroid; 3beta-hydroxy-Delta(5)-steroid; oxysterol
10-gingerol [no description available]	3.25	1	0	beta-hydroxy ketone; monomethoxybenzene; phenols
3-(2-carboxyindol-3-yl)propionic acid 3-(2-carboxyindol-3-yl)propionic acid: structure given in first source; NMDA antagonist	2.17	1	0
biotin vitamin B7 : Any member of a group of vitamers that belong to the chemical structural class called biotins that exhibit biological activity against vitamin B7 deficiency. Vitamin B7 deficiency is very rare in individuals who take a normal balanced diet. Foods rich in biotin are egg yolk, liver, cereals, vegetables (spinach, mushrooms) and rice. Symptoms associated with vitamin B7 deficiency include thinning hair, scaly skin rashes around eyes, nose and mouth, and brittle nails. The vitamers include biotin and its ionized and salt forms.	7.44	2	0	biotins; vitamin B7	coenzyme; cofactor; Escherichia coli metabolite; fundamental metabolite; human metabolite; mouse metabolite; nutraceutical; prosthetic group; Saccharomyces cerevisiae metabolite
angiotensin ii Giapreza: injectable form of angiotensin II used to increase blood pressure in adult patients with septic or other distributive shock. Ile(5)-angiotensin II : An angiotensin II that acts on the central nervous system (PDB entry: 1N9V).	7.52	2	0	amino acid zwitterion; angiotensin II	human metabolite
pinoresinol diglucoside pinoresinol diglucoside: major antihypertensive principle of Tu-Chung (Eucummia ulmoides, Oliver); structure	2.25	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.	4.51	22	0
sb 203580 [no description available]	2.48	2	0	imidazoles; monofluorobenzenes; pyridines; sulfoxide	EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector; Hsp90 inhibitor; neuroprotective agent
erlotinib hydrochloride [no description available]	5.09	1	1	hydrochloride; terminal acetylenic compound	antineoplastic agent; protein kinase inhibitor
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
7-epipaclitaxel [no description available]	2.15	1	0
scutellarin scutellarin: see scutellarein for aglycone. scutellarin : The glycosyloxyflavone which is the 7-O-glucuronide of scutellarein.	7.77	3	0	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.	1.99	1	0	aflatoxin; aromatic ether; aromatic ketone	carcinogenic agent; human metabolite
glycitin glycitin: structure in first source. glycitin : A glycosyloxyisoflavone that is isoflavone substituted by a methoxy group at position 6, a hydroxy group at position 4' and a beta-D-glucopyranosyloxy group at position 7.	2.04	1	0	7-hydroxyisoflavones 7-O-beta-D-glucoside; hydroxyisoflavone; methoxyisoflavone; monosaccharide derivative	plant metabolite
1,4,7-triazacyclononane 1,4,7-triazacyclononane: structure given in first source	2.06	1	0	azacycloalkane; crown amine; saturated organic heteromonocyclic parent
4-sulfocatechol 4-sulfocatechol: structure in first source. 3,4-dihydroxybenzenesulfonic acid : A benzene ring substituted with a sulphonic acid group at position C-1, and hydroxy groups at C-3 and C-4.	2.03	1	0	dihydroxybenzenesulfonic acid	metabolite
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.	2.05	1	0
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.	2.06	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; C29-steroid; phytosterols; stigmastane sterol	anticholesteremic drug; antioxidant; mouse metabolite; plant metabolite; sterol methyltransferase inhibitor
nsc13345 NSC13345: structure in first source	2.13	1	0	amidobenzoic acid
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.	2.13	1	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.	2.5	2	0	arenecarbaldehyde; furans; primary alcohol	indicator; Maillard reaction product
lanosterol [no description available]	2.05	1	0	14alpha-methyl steroid; 3beta-sterol; tetracyclic triterpenoid	bacterial metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	3.17	5	0
lupeol [no description available]	3.9	3	0	pentacyclic triterpenoid; secondary alcohol	anti-inflammatory drug; plant metabolite
methyl 3,4-dihydroxybenzoate [no description available]	3.3	6	0	catechols; methyl ester	antioxidant; neuroprotective agent; plant metabolite
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).	2.46	2	0	aromatic ether; lignan; oxolanes; phenols; primary alcohol	antifungal agent; plant metabolite
amyrin acetate [no description available]	2.46	2	0
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.	3.29	6	0	(dihydroxyphenyl)propanoic acid	antioxidant; human xenobiotic metabolite
jatrorrhizine chloride [no description available]	2.07	1	0
pomolic acid pomolic acid: from Rosa woodsii & Hyptis capitata; structure in first source	3.25	1	0	triterpenoid	metabolite
5-amino-8-hydroxyquinoline 5-amino-8-hydroxyquinoline: structure in first source	2.11	1	0
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.	2.07	1	0
arabinose [no description available]	2.01	1	0	L-arabinose	Escherichia coli metabolite; mouse metabolite
hexacyanoferrate iii hexacyanoferrate III: RN given refers to parent cpd	2.02	1	0
mevalonic acid Mevalonic Acid: A dihydroxy monocarboxylic acid and precursor in the biosynthetic pathway known as the mevalonate pathway, which produces terpenes and steroids that are vital for diverse cellular functions.. mevalonic acid : A racemate composed of equimolar amounts of (R)- and (S)-mevalonic acid.. (R)-mevalonic acid : The (R)-enantiomer of mevalonic acid.	5.12	2	1	3,5-dihydroxy-3-methylpentanoic acid
naringenin (S)-naringenin : The (S)-enantiomer of naringenin.	3.01	4	0	(2S)-flavan-4-one; naringenin	expectorant; plant metabolite
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.	2.02	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
3,4-dihydroxyphenyllactic acid 3,4-dihydroxyphenyllactic acid: from S. miltiorhiza Bge; dilates coronary artery; RN given refers to parent cpd without isomeric designation	3.91	12	0	2-hydroxy monocarboxylic acid; catechols
scopolin [no description available]	2.1	1	0	beta-D-glucoside; coumarins; monosaccharide derivative	plant metabolite
taxifolin (+)-taxifolin : A taxifolin that has (2R,3R)-configuration.	2.97	4	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.	2.01	1	0	tartaric acid	Escherichia coli metabolite
eriodictyol eriodictyol: structure. eriodictyol : A tetrahydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5, 7, 3' and 4' respectively.	2.79	3	0	3'-hydroxyflavanones; tetrahydroxyflavanone
pelargonidin pelargonidin: influences flower phenotype. pelargonidin : An anthocyanidin cation that is flavylium substituted by a hydroxy groups at positions 3, 5, 7 and 4'.	3.61	2	0	5-hydroxyanthocyanidin	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.	3.32	6	0	beta-D-glucoside; monosaccharide derivative	Escherichia coli metabolite; plant metabolite
limonene-1,2-epoxide limonene-1,2-epoxide: RN given refers to cpd without isomeric designation. (4R)-limonene 1,2-epoxide : The (R)-enantiomer of limonene 1,2-epoxide.	3.25	1	0	limonene 1,2-epoxide
silychristin silychristin : A flavonolignan isolated from Silybum marianum and has been shown to exhibit inhibitory activities against lipoxygenase and prostaglandin synthetase.	2.05	1	0	1-benzofurans; aromatic ether; flavonolignan; polyphenol; secondary alpha-hydroxy ketone	lipoxygenase inhibitor; metabolite; prostaglandin antagonist; radical scavenger
ginsenoside rg1 [no description available]	7.55	2	0	12beta-hydroxy steroid; 3beta-hydroxy-4,4-dimethylsteroid; beta-D-glucoside; ginsenoside; tetracyclic triterpenoid	neuroprotective agent; pro-angiogenic agent
notoginsenoside r1 notoginsenoside R1 : A ginsenoside found in Panax notoginseng that is dammarane which is substituted by hydroxy groups at the 3beta, 6alpha, 12beta and 20 pro-S positions, in which the hydroxy groups at positions 6 and 20 have been converted to the corresponding beta-D-xylopyranosyl-(1->2)-beta-D-glucopyranoside and beta-D-glucopyranoside respectively, and in which a double bond has been introduced at the 24-25 position.	7.15	1	0	12beta-hydroxy steroid; 3beta-hydroxy-4,4-dimethylsteroid; 3beta-hydroxy steroid; beta-D-glucoside; disaccharide derivative; ginsenoside; tetracyclic triterpenoid	antioxidant; apoptosis inducer; neuroprotective agent; phytoestrogen; plant metabolite
glaucolide b glaucolide B: sesquiterpene lactone from Veronia eremophila; antimicrobial cpd; structure given in first source; RN from CA Index Guide	2.17	1	0	carboxylic ester; ketone
farrerol farrerol: expectorant principle isolated from leaves of Rhododendron dauricum L; structure	2.11	1	0	organic molecular entity	metabolite
naringin [no description available]	4.24	5	0	(2S)-flavan-4-one; 4'-hydroxyflavanones; dihydroxyflavanone; disaccharide derivative; neohesperidoside	anti-inflammatory agent; antineoplastic agent; metabolite
ochratoxin a ochratoxin A: structure in first source & in Merck, 9th ed, #6549. ochratoxin A : A phenylalanine derivative resulting from the formal condensation of the amino group of L-phenylalanine with the carboxy group of (3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carboxylic acid (ochratoxin alpha). It is among the most widely occurring food-contaminating mycotoxins, produced by Aspergillus ochraceus, Aspergillus carbonarius and Penicillium verrucosum.	2.47	2	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
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.	3.25	1	0	beta-hydroxy ketone; guaiacols	antineoplastic agent; plant metabolite
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)	3.51	7	0
syringaresinol (+)-syringaresinol : The (7alpha,7'alpha,8alpha,8'alpha)-stereoisomer of syringaresinol.	2.02	1	0	syringaresinol	antineoplastic agent
acanthoside b acanthoside B: isolated from the herb Huanghuaren; RN given refers to (1S-(1alpha,3aalpha,4alpha,6aalpha))-isomer	2.51	2	0	beta-D-glucoside	metabolite
geniposidic acid [no description available]	2.47	2	0	terpene glycoside
epiafzelechin epiafzelechin: antioxidant; 3'-deoxy form of epicatechin; structure in first source. (-)-epiafzelechin : A catechin derivative having (2R,3R)-configuration.	2.07	1	0	catechin	plant metabolite
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	2.21	1	0	cyclodextrin
acarbose [no description available]	2.51	2	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.	1.97	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	4.04	13	0	cinnamic acid	plant metabolite
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.	2.43	2	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.	2.08	1	0	butenedioic acid	food acidity regulator; fundamental metabolite; geroprotector
resveratrol trans-resveratrol : A resveratrol in which the double bond has E configuration.	2.97	4	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).	1.98	1	0	retinol; vitamin A	human metabolite; mouse metabolite; plant metabolite
oleic acid Oleic Acid: An unsaturated fatty acid that is the most widely distributed and abundant fatty acid in nature. It is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. (Stedman, 26th ed). oleic acid : An octadec-9-enoic acid in which the double bond at C-9 has Z (cis) stereochemistry.	8.19	5	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.	6.56	59	0	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.	2.53	2	0	D-galactopyranuronic acid
t0901317 T0901317: an LXRalpha and LXRbeta agonist	2.08	1	0
roflumilast [no description available]	2.01	1	0	aromatic ether; benzamides; chloropyridine; cyclopropanes; organofluorine compound	anti-asthmatic drug; phosphodiesterase IV inhibitor
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).	1.99	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)	2.42	2	0	actinomycin	mutagen
conidendrin conidendrin: RN given for (3aR-(3aalpha,4alpha,9alpha,9abeta))-isomer; a phenyl-naphthyl-furanolactone	2.15	1	0	lignan	metabolite
gamma-sitosterol clionasterol : A member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3.	3.92	12	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; phytosterols	marine metabolite; plant metabolite
5-carboxy-8-hydroxyquinoline 5-carboxy-8-hydroxyquinoline: a JmjC histone demethylase inhibitor; structure in first source	2.08	1	0	quinolines
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	1	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
potassium bicarbonate potassium hydrogencarbonate : A potassium salt that is the monopotassium salt of carbonic acid. It has fungicidal properties and is used in organic farming for the control of powdery mildew and apple scab.	2.05	1	0	organic salt; potassium salt	antifungal agrochemical; buffer; food acidity regulator; raising agent
cinnamaldehyde 3-phenylprop-2-enal : A member of the class of cinnamaldehydes that is prop-2-enal in which a hydrogen at position 3 has been replaced by a phenyl group. The configuration of the double bond is not specified; the name "cinnamaldehyde" is widely used to refer to the E (trans) isomer.. (E)-cinnamaldehyde : The E (trans) stereoisomer of cinnamaldehyde, the parent of the class of cinnamaldehydes.	3.88	3	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
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.	4.14	4	0	2-coumaric acid; phenols	antioxidant; metabolite
3-coumaric acid 3-coumaric acid: RN given refers to cpd without isomeric designation in Chemline. trans-3-coumaric acid : A 3-coumaric acid that is phenol substituted with trans-2-propenoic acid at position C-3.. 3-coumaric acid : A monohydroxycinnamic acid in which the hydroxy substituent is located at C-3 of the phenyl ring.	3.25	1	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.	6.19	41	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.	3.25	1	0	anethole	flavouring agent
glycosides [no description available]	3.93	12	0
chalcone trans-chalcone : The trans-isomer of chalcone.	2.8	3	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.	4.89	10	0	sinapic acid	MALDI matrix material; plant metabolite
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	7.97	4	0	stilbene
isoliquiritigenin [no description available]	2.15	1	0	chalcones	antineoplastic agent; biological pigment; EC 1.14.18.1 (tyrosinase) inhibitor; GABA modulator; geroprotector; metabolite; NMDA receptor antagonist
phenyl-n-tert-butylnitrone phenyl-N-tert-butylnitrone: a spin-trapping agent	2.41	2	0
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.	3.75	10	0	alpha,beta-unsaturated monocarboxylic acid; sorbic acid
gw9662 2-chloro-5-nitrobenzanilide: pretreatment of peroxisome proliferator activated receptors with GW9662 results in the irreversible loss of ligand binding	2.11	1	0	benzamides
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.	5.09	1	1	inorganic sodium salt	food antioxidant
sesquiterpenes [no description available]	2.74	3	0
methylthiouracil Methylthiouracil: A thiourea antithyroid agent that inhibits the synthesis of thyroid hormone. It is used in the treatment of hyperthyroidism.	2.06	1	0	pyrimidone
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.	2.49	2	0	catechols; polyphenol; resorcinols; stilbenol	antineoplastic agent; apoptosis inducer; geroprotector; hypoglycemic agent; plant metabolite; protein kinase inhibitor; tyrosine kinase inhibitor
4,6-dimethyl-2-thiopyrimidine 4,6-dimethyl-2-thiopyrimidine: structure	2.06	1	0
ethyl coumarate ethyl coumarate: structure in first source	2.53	2	0	cinnamate ester
caffeic acid trans-caffeic acid : The trans-isomer of caffeic acid.	8.21	78	1	caffeic acid	geroprotector; mouse metabolite
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.	2.78	3	0	ferulic acids	antioxidant; biomarker; metabolite
4-(4-(4-chloro-phenyl)thiazol-2-ylamino)phenol [no description available]	2.11	1	0	substituted aniline
ethyl 2,4-dihydroxybenzoate ethyl 2,4-dihydroxybenzoate: isolated from Artocarpus elasticus; structure in first source	2.08	1	0
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.	3.76	2	0	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
nootkatone nootkatone: RN given refers to cpd without isomeric designation; structure given in first source. (+)-nootkatone : A sesquiterpenoid that is 4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one which is substituted by methyl groups at positions 4 and 4a, and by an isopropenyl group at position 6 (the 4R,4aS,6R stereoisomer).	2.6	1	0	carbobicyclic compound; enone; sesquiterpenoid	fragrance; insect repellent; plant metabolite
thiouracil Thiouracil: Occurs in seeds of Brassica and Crucifera species. Thiouracil has been used as antithyroid, coronary vasodilator, and in congestive heart failure although its use has been largely supplanted by other drugs. It is known to cause blood dyscrasias and suspected of terato- and carcinogenesis.. thiouracil : A nucleobase analogue that is uracil in which the oxo group at C-2 is replaced by a thioxo group.	2.06	1	0	nucleobase analogue; thiocarbonyl compound	antithyroid drug; metabolite
coniferyl alcohol coniferyl alcohol: structure. coniferol : A phenylpropanoid that is one of the main monolignols, produced by the reduction of the carboxy functional group in cinnamic acid and the addition of a hydroxy and a methoxy substituent to the aromatic ring.	2.03	1	0	guaiacols; phenylpropanoid	animal metabolite; monolignol; mouse metabolite; pheromone; plant metabolite; volatile oil component
chlorogenic acid caffeoylquinic acid: Antiviral Agent; structure in first source. chlorogenate : A monocarboxylic acid anion that is the conjugate base of chlorogenic acid; major species at pH 7.3.	8.36	50	2	cinnamate ester; tannin	food component; plant metabolite
indigo carmine Indigo Carmine: Indolesulfonic acid used as a dye in renal function testing for the detection of nitrates and chlorates, and in the testing of milk.. indigo carmine : An organic sodium salt resulting from the formal condensation of indigo carmine (acid form) with two equivalents of sodium hydroxide. It is an indicator at pH 11.5-14, changing from blue to yellow.	5.09	1	1
D-fructopyranose [no description available]	2.61	2	0	cyclic hemiketal; D-fructose; fructopyranose	sweetening agent
thioacetamide Thioacetamide: A crystalline compound used as a laboratory reagent in place of HYDROGEN SULFIDE. It is a potent hepatocarcinogen.. thioacetamide : A thiocarboxamide consiting of acetamide having the oxygen replaced by sulfur.	7.76	2	0	thiocarboxamide	hepatotoxic agent
4-thiouracil [no description available]	2.06	1	0
nadp [no description available]	2.44	2	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)	5.42	22	0
scopolamine [no description available]	2.17	1	0	3-hydroxy carboxylic acid
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.	2.03	1	0
cobaltous chloride cobaltous chloride: RN given refers to unlabeled cpd; RN in Chemline for cobalt trichloride: 10241-04-0; RN for 60-labeled cpd: 14543-09-0; RN for 57-labeled cpd: 164113-89-1; RN for 58-labeled cpd: 29377-09-1; structure. cobalt dichloride : A cobalt salt in which the cobalt metal is in the +2 oxidation state and the counter-anion is chloride. It is used as an indicator for water in desiccants.	3.17	1	0	cobalt salt; inorganic chloride	allergen; calcium channel blocker; sensitiser; two-colour indicator
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.	5.09	1	1	nitrogen oxide
oxalylglycine oxalylglycine: structure given in first source. N-oxalylglycine : An amino dicarboxylic acid that is iminodiacetic acid with an oxo substituent. It is used as an inhibitor of alpha-ketoglutarate dependent (EC 1.14.11.*) enzymes.	2.47	2	0	amino dicarboxylic acid; N-acylglycine	EC 1.14.11.* (oxidoreductase acting on paired donors, 2-oxoglutarate as one donor, incorporating 1 atom each of oxygen into both donors) inhibitor
pelargonidin-3-glucoside pelargonidin-3-glucoside: structure given in first source; RN given for chloride salt; RN for parent cpd not available 1/93. pelargonidin 3-O-beta-D-glucoside chloride : A member of the class of anthocyanin chlorides that has pelargonidin 3-O-beta-D-glucoside as the cationic counterpart.	2.83	3	0	anthocyanin chlorides
cytellin cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982	4.25	17	0
ginsenosides ginsenoside : Triterpenoid saponins with a dammarane-like skeleton originally isolated from ginseng (Panax) species. Use of the term has been extended to include semi-synthetic derivatives.	2.55	2	0
ovalbumin Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.	7.54	2	0
3-hydroxy-2-methyl-4h-pyran-4-thione 3-hydroxy-2-methyl-4H-pyran-4-thione: inhibits Bla2 beta-lactamase; structure in first source	2.06	1	0
am 630 iodopravadoline: an aminoalkylindole; a competitive cannabinoid receptor antagonist; structure given in first source	2.21	1	0	N-acylindole
tolcapone Tolcapone: A benzophenone and nitrophenol compound that acts as an inhibitor of CATECHOL O-METHYLTRANSFERASE, an enzyme involved in the metabolism of DOPAMINE and LEVODOPA. It is used in the treatment of PARKINSON DISEASE in patients for whom levodopa is ineffective or contraindicated.. tolcapone : Benzophenone substituted on one of the phenyl rings at C-3 and C-4 by hydroxy groups and at C-5 by a nitro group, and on the other phenyl ring by a methyl group at C-4. It is an inhibitor of catechol O-methyltransferase.	2.21	1	0	2-nitrophenols; benzophenones; catechols	antiparkinson drug; EC 2.1.1.6 (catechol O-methyltransferase) inhibitor
catechin gallate catechin gallate: structure in first source. (+)-catechin-3-O-gallate : A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3S)-hydroxy group of (+)-catechin.	7.47	2	0	flavans; gallate ester; polyphenol	metabolite
quercetin [no description available]	5.26	48	0	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
biochanin a [no description available]	2.04	1	0	4'-methoxyisoflavones; 7-hydroxyisoflavones	antineoplastic agent; EC 3.5.1.99 (fatty acid amide hydrolase) inhibitor; phytoestrogen; plant metabolite; tyrosine kinase inhibitor
formononetin [no description available]	2.77	3	0	4'-methoxyisoflavones; 7-hydroxyisoflavones	phytoestrogen; plant metabolite
acacetin 5,7-dihydroxy-4'-methoxyflavone : A monomethoxyflavone that is the 4'-methyl ether derivative of apigenin.	2.15	1	0	dihydroxyflavone; monomethoxyflavone	anticonvulsant; plant metabolite
apigenin Chamomile: Common name for several daisy-like plants (MATRICARIA; TRIPLEUROSPERMUM; ANTHEMIS; CHAMAEMELUM) native to Europe and Western Asia, now naturalized in the United States and Australia.	8.7	9	0	trihydroxyflavone	antineoplastic agent; metabolite
luteolin [no description available]	3.77	10	0	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.	2.58	2	0	4'-methoxyisoflavones; 7-hydroxyisoflavones	antioxidant; metabolite
linoleic acid Linoleic Acid: A doubly unsaturated fatty acid, occurring widely in plant glycosides. It is an essential fatty acid in mammalian nutrition and is used in the biosynthesis of prostaglandins and cell membranes. (From Stedman, 26th ed). linoleic acid : An octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry.	3.14	5	0	octadecadienoic acid; omega-6 fatty acid	algal metabolite; Daphnia galeata metabolite; plant metabolite
quercitrin [no description available]	8.39	6	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]	3.15	5	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.	3.52	7	0	carotenoid beta-end derivative; cyclic carotene	antioxidant; biological pigment; cofactor; ferroptosis inhibitor; human metabolite; mouse metabolite; plant metabolite; provitamin A
maleoylacetic acid maleoylacetic acid: RN given refers to (Z)-isomer. maleylacetic acid : A 4-oxohex-2-enedioic acid with a Z-configuration.. 4-oxohex-2-enedioate : An oxo dicarboxylate that is the conjugate base of 4-oxohex-2-enedioic acid.. maleylacetate : A 4-oxohex-2-enedioate that is the conjugate base of maleylacetic acid.	2.03	1	0	4-oxohex-2-enedioic acid	bacterial xenobiotic metabolite
coniferaldehyde coniferaldehyde: from aqueous extract of Senra incana. coniferyl aldehyde : A member of the class of cinnamaldehydes that is cinnamaldehyde substituted by a hydroxy group at position 4 and a methoxy group at position 3.	2.05	1	0	cinnamaldehydes; guaiacols; phenylpropanoid	antifungal agent; plant metabolite
feruloyltyramine feruloyltyramine: structure given in first source; isolated from Cannabis sativa seeds, roots, leaves, and resin; induces hypothermia and motor incoordination in mice; moupinamide is (E)-isomer	2.05	1	0	tyramines	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.	2.17	1	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.	2.51	2	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.	2.75	3	0	monomethoxyflavone; trihydroxyflavone	antineoplastic agent; antioxidant; metabolite
quercetin 3-o-methyl ether quercetin 3-O-methyl ether: from Rhamnus species; structure in first source. 3',4',5,7-tetrahydroxy-3-methoxyflavone : A tetrahydroxyflavone having the 4-hydroxy groups located at the 3'- 4'- 5- and 7-positions as well as a methoxy group at the 2-position.	2.49	2	0	monomethoxyflavone; tetrahydroxyflavone	antimicrobial agent; metabolite
apigetrin apigetrin: structure given in first source. apigenin 7-O-beta-D-glucoside : A glycosyloxyflavone that is apigenin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	2.17	1	0	beta-D-glucoside; dihydroxyflavone; glycosyloxyflavone; monosaccharide derivative	antibacterial agent; metabolite; non-steroidal anti-inflammatory drug
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.	3.18	5	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; phytosterols; stigmastane sterol	plant metabolite
quercetin 3-o-glucopyranoside quercetin 3-O-glucopyranoside: structure in first source. quercetin 3-O-beta-D-glucopyranoside : A quercetin O-glucoside that is quercetin with a beta-D-glucosyl residue attached at position 3. Isolated from Lepisorus contortus, it exhibits antineoplastic activityand has been found to decrease the rate of polymerization and sickling of red blood cells	3.16	5	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.	7.07	22	0	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite
kaempferol [no description available]	9.19	16	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.	2.15	1	0	prostaglandins Falpha	human metabolite; mouse metabolite
genistein [no description available]	4.62	4	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
entacapone entacapone: structure given in first source. entacapone : A monocarboxylic acid amide that is N,N-diethylprop-2-enamide in which the hydrogen at position 2 is substituted by a cyano group and the hydrogen at the 3E position is substituted by a 3,4-dihydroxy-5-nitrophenyl group.	2.21	1	0	2-nitrophenols; catechols; monocarboxylic acid amide; nitrile	antidyskinesia agent; antiparkinson drug; central nervous system drug; EC 2.1.1.6 (catechol O-methyltransferase) inhibitor
erucic acid [no description available]	2.07	1	0	docosenoic acid
butein [no description available]	2.1	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
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	2.1	1	0	1-benzofurans
spinasterol spinasterol: RN given refers to alpha-spinasterol ((3beta,5alpha,22E)-isomer)	2.21	1	0	steroid
5,7-dihydroxychromone 5,7-dihydroxychromone: isolated from the roots of Bauhinia hupehara	2.11	1	0	chromones
genistin genistin: glycoside of soy bean isoflavone, gentistein	2.46	2	0	7-hydroxyisoflavones 7-O-beta-D-glucoside
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.	7.45	2	0	hydroxycoumarin	antioxidant; plant metabolite; ultraviolet filter
esculin [no description available]	2.11	1	0	beta-D-glucoside; hydroxycoumarin	antioxidant; metabolite
7-hydroxycoumarin 7-oxycoumarin: derivatives have anti-oxidant properties. umbelliferone : A hydroxycoumarin that is coumarin substituted by a hydroxy group ay position 7.	2.17	1	0	hydroxycoumarin	fluorescent probe; food component; plant metabolite
budlein a budlein A: anti-inflammatory and analgesic sesquiterpene lactone from Viguiera robusta; structure in first source	2.17	1	0	sesquiterpenoid
costunolide [no description available]	2.07	1	0	germacranolide; heterobicyclic compound	anthelminthic drug; antiinfective agent; antineoplastic agent; antiparasitic agent; antiviral drug; metabolite
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.	1.99	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
amentoflavone [no description available]	2.02	1	0	biflavonoid; hydroxyflavone; ring assembly	angiogenesis inhibitor; antiviral agent; cathepsin B inhibitor; P450 inhibitor; plant metabolite
baicalein [no description available]	2.46	2	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.	9.1	4	0	7-hydroxyflavonol; dihydroxyflavone	anti-inflammatory agent; antineoplastic agent; antioxidant; EC 2.7.11.18 (myosin-light-chain kinase) inhibitor; hepatoprotective agent; plant metabolite
3,7,4'-trihydroxyflavone 3,7,4'-trihydroxyflavone: structure in first source	2.1	1	0	hydroxyflavan
diosmetin [no description available]	2.08	1	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
fisetin [no description available]	2.52	2	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.	2.63	2	0	7-hydroxyflavonol; trihydroxyflavone	antimicrobial agent; EC 3.1.1.3 (triacylglycerol lipase) inhibitor; plant metabolite
euxanthone euxanthone : A member of the class of xanthones that is 9H-xanthene substituted by hydroxy group at positions 1 and 7 and an oxo group at position 9. It has been isolated from Cratoxylum cochinchinense.	2.03	1	0	phenols; xanthones	metabolite; 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.	8.23	5	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	2.01	1	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.	2.99	4	0	7-hydroxyflavonol; monomethoxyflavone; tetrahydroxyflavone	anticoagulant; EC 1.14.18.1 (tyrosinase) inhibitor; metabolite
myricetin [no description available]	3.17	5	0	7-hydroxyflavonol; hexahydroxyflavone	antineoplastic agent; antioxidant; cyclooxygenase 1 inhibitor; food component; geroprotector; hypoglycemic agent; plant metabolite
myricitrin myricitrin: isolated from root bark of Myrica cerifera L.; structure. myricitrin : A glycosyloxyflavone that consists of myricetin attached to a alpha-L-rhamnopyranosyl residue at position 3 via a glycosidic linkage. Isolated from Myrica cerifera, it exhibits anti-allergic activity.	2.02	1	0	alpha-L-rhamnoside; glycosyloxyflavone; monosaccharide derivative; pentahydroxyflavone	anti-allergic agent; EC 1.14.13.39 (nitric oxide synthase) inhibitor; EC 2.7.11.13 (protein kinase C) inhibitor; plant metabolite
orientin orientin: structure given in first source; RN given refers to the (D-glucopyranosyl)-isomer. orientin : A C-glycosyl compound that is luteolin substituted by a beta-D-glucopyranosyl moiety at position 8.	2.03	1	0	3'-hydroxyflavonoid; C-glycosyl compound; tetrahydroxyflavone	antioxidant; metabolite
patuletin patuletin: structure given in first source; inhibits aldose reductase in rat lens. patuletin : A trimethoxyflavone that is quercetagetin methylated at position 6.	2.06	1	0	flavonols; monomethoxyflavone; pentahydroxyflavone	analgesic; antioxidant; EC 1.1.1.21 (aldehyde reductase) inhibitor; lipoxygenase inhibitor; metabolite
santin santin: from Tanacetum microphyllum; structure given in first source. santin : A trimethoxyflavone that is flavone substituted by methoxy groups at positions 3, 6 and 4' and hydroxy groups at positions 5 and 7 respectively.	2.17	1	0	dihydroxyflavone; trimethoxyflavone	plant metabolite
tamarixetin tamarixetin: isolated from Costsus spicatus. tamarixetin : A monomethoxyflavone that is quercetin methylated at position O-4'. Isolated from Cyperus teneriffae.	2.17	1	0	7-hydroxyflavonol; monomethoxyflavone; tetrahydroxyflavone	antioxidant; metabolite
tricin tricin: from Spartina cynosuroides and other plants; structure	2.04	1	0	3'-methoxyflavones; dimethoxyflavone; trihydroxyflavone	EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; metabolite
wogonin wogonin: structure in first source. wogonin : A dihydroxy- and monomethoxy-flavone in which the hydroxy groups are positioned at C-5 and C-7 and the methoxy group is at C-8.	2.44	2	0	dihydroxyflavone; monomethoxyflavone	angiogenesis inhibitor; antineoplastic agent; cyclooxygenase 2 inhibitor; plant metabolite
daidzein [no description available]	2.45	2	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
trans-2,3',4,5'-tetrahydroxystilbene trans-2,3',4,5'-tetrahydroxystilbene: hydroxystilbene oxyresveratrol	2.06	1	0	stilbenoid
chicoric acid chicoric acid: inhibits HIV-1 integrase	2.03	1	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	2.11	1	0	alkyl caffeate ester; quinic acid	plant metabolite
gingerenone a gingerenone A: has antineoplastic activity; isolated from Zingiber officinale; structure in first source	3.25	1	0	diarylheptanoid
3,4-di-o-caffeoylquinic acid 3,4-di-O-caffeoylquinic acid: isolated from Siphonostegia chinensis	2.52	2	0	quinic acid
caffeic acid phenethyl ester phenethyl caffeate : An alkyl caffeate ester in which 2-phenylethyl is the alkyl component.	2.21	1	0	alkyl caffeate ester	anti-inflammatory agent; antibacterial agent; antineoplastic agent; antioxidant; antiviral agent; immunomodulator; metabolite; neuroprotective agent
rosmarinic acid rosmarinic acid: RN given refers to parent cpd; promote OT project. (R)-rosmarinic acid : A stereoisomer of rosmarinic acid having (R)-configuration.. rosmarinic acid : The 1-carboxy-2-(2,4-dihydroxyphenyl)ethyl ester of trans-caffeic acid.	2.44	2	0	rosmarinic acid	geroprotector; plant metabolite
salvianolic acid a salvianolic acid A: a nootropic depside from Salvia miltiorrhizia	3.17	5	0	stilbenoid
shogaol shogaol: from ginger, ZINGIBER OFFICINALE; less mutagenic than GINGEROL; structure given in first source	3.25	1	0	enone; monomethoxybenzene; phenols
acteoside acteoside: a protein kinase C inhibitor with hepatoprotective, anti-asthmatic, and analgesic activities; a phenylethanoid glycoside related to isoacteoside; from leaves of Lippia multiflora (Verbenaceae). acteoside : A glycoside that is the alpha-L-rhamnosyl-(1->3)-beta-D-glucoside of hydroxytyrosol in which the hydroxy group at position 4 of the glucopyranosyl moiety has undergone esterification by formal condensation with trans-caffeic acid.	2.05	1	0	catechols; cinnamate ester; disaccharide derivative; glycoside; polyphenol	anti-inflammatory agent; antibacterial agent; antileishmanial agent; neuroprotective agent; plant metabolite
4'-methoxy-3',5,7-trihydroxyisoflavone 4'-methoxy-3',5,7-trihydroxyisoflavone: structure in first source. pratensein : A member of the class of 7-hydroxyisoflavones in which isoflavone is substituted by hydroxy groups at the 5, 7, and 3' positions, and by a methoxy group at the 4' position.	2.15	1	0	4'-methoxyisoflavones; 7-hydroxyisoflavones
wighteone wighteone : A member of the class of 7-hydroxyisoflavones that is isoflavone substituted by hydroxy groups at positions 5, 7 and 4' and a prenyl group at position 6. It has been isolated from Ficus mucuso.	2.06	1	0	7-hydroxyisoflavones	antifungal agent; plant metabolite
ellagic acid [no description available]	3.64	9	0	catechols; cyclic ketone; lactone; organic heterotetracyclic compound; polyphenol	antioxidant; EC 1.14.18.1 (tyrosinase) inhibitor; EC 2.3.1.5 (arylamine N-acetyltransferase) inhibitor; EC 2.4.1.1 (glycogen phosphorylase) inhibitor; EC 2.5.1.18 (glutathione transferase) inhibitor; EC 2.7.1.127 (inositol-trisphosphate 3-kinase) inhibitor; EC 2.7.1.151 (inositol-polyphosphate multikinase) inhibitor; EC 2.7.4.6 (nucleoside-diphosphate kinase) inhibitor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; EC 5.99.1.2 (DNA topoisomerase) inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; food additive; fungal metabolite; geroprotector; plant metabolite; skin lightening agent
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.	2.49	2	0	beta-D-glucoside; kaempferol O-glucoside; monosaccharide derivative; trihydroxyflavone	plant metabolite; trypanocidal drug
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.	2.15	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.	2.13	1	0	4-hydroxynon-2-enal; 4-hydroxynonenal
ubiquinone 6 [no description available]	2.06	1	0	ubiquinones	Saccharomyces cerevisiae metabolite
3',4',7-trihydroxyisoflavone 3',4',7-trihydroxyisoflavone: from Streptomyces sp OH-1049; structure given in first source. 3',4',7-trihydroxyisoflavone : A 7-hydroxyisoflavone that is daidzein substituted by a hydroxy group at position 3'.	2.15	1	0	7-hydroxyisoflavones	antineoplastic agent; EC 1.3.1.22 [3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+))] inhibitor; metabolite
isochlorogenic acid [no description available]	2.1	1	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).	2.47	2	0	cinnamyl alcohol	plant metabolite
corylin corylin: from Psoralea corylifolia (Leguminosae), has osteoblastic proliferation stimulating activity; structure in first source	2.06	1	0
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.	2.11	1	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.	7.46	2	0	beta-D-glucoside; dimethoxybenzene; monosaccharide derivative; primary alcohol	hepatoprotective agent; plant metabolite
ethyl caffeate (E)-ethyl 3-(3,4-dihydroxyphenyl)prop-2-enoate: structure in first source. ethyl trans-caffeate : An ethyl ester resulting from the formal condensation of the carboxy group of trans-caffeic acid with ethanol.	2.21	1	0	alkyl caffeate ester; ethyl ester; hydroxycinnamic acid	anti-inflammatory agent; antineoplastic agent; metabolite
fustin fustin : A dihydroflavonol that is the 2,3-dihydro derivative of fisetin.. tetrahydroxyflavanone : A hydroxyflavanone with atleast four hydroxy substituents.	2.1	1	0
glycitein glycitein : A methoxyisoflavone that is isoflavone substituted by a methoxy group at position 6 and hydroxy groups at positions 7 and 4'. It has been isolated from the mycelia of the fungus Cordyceps sinensis.	2.04	1	0	7-hydroxyisoflavone; methoxyisoflavone	fungal metabolite; phytoestrogen; plant metabolite
calycosin-7-o-beta-d-glucopyranoside calycosin-7-O-beta-D-glucoside: from Radix Astragali. calycosin-7-O-beta-D-glucoside : A glycosyloxyisoflavone that is calycosin substituted by a beta-D-glucopyranosyl residue at position at 7 via a glycosidic linkage.	2.15	1	0	4'-methoxyisoflavones; 7-hydroxyisoflavones 7-O-beta-D-glucoside; hydroxyisoflavone; monosaccharide derivative
isofraxidin isofraxidin: also see fraxidin	7.03	1	0	hydroxycoumarin
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.	2.11	1	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.	2.84	3	0	disaccharide derivative; kaempferol O-glucoside; rutinoside; trihydroxyflavone	metabolite; plant metabolite; radical scavenger
icariin [no description available]	2.1	1	0	flavonols; glycosyloxyflavone	antioxidant; bone density conservation agent; EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor; phytoestrogen
martynoside martynoside: isolated from Verbena bipinnatifida Nutt; structure in first source	2.05	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
neoisoliquiritin neoisoliquiritin: inhibits angiogenesis; isolated from licorice root; isoliquiritin is the (E)-isomer; structure in first source; isoliquiritin is also available	2.25	1	0	flavonoids; glycoside
octadecyl caffeate caffeic acid n-octadecyl ester: isolated from Daphne acutiloba Rehd; structure in first source	2.15	1	0
tiliroside tiliroside: isolated from seeds of Eremocarpus setigerus	2.41	1	0	cinnamate ester; glycosyloxyflavone; monosaccharide derivative; trihydroxyflavone	plant metabolite
quercetin 3-o-gentiobioside quercetin 3-O-gentiobioside: an antioxidant with hypoglycemic and anticholesteremic activities; structure in first source. quercetin 3-beta-gentiobioside : A quercetin O-glycoside in which the hydroxy hydrogen at position 3 of quercetin has been replaced by a gentiobiosyl group.	2.63	2	0	disaccharide derivative; quercetin O-glycoside; tetrahydroxyflavone	Brassica napus 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'.	2.59	2	0	beta-D-glucoside; flavonols; monosaccharide derivative; quercetin O-glucoside; tetrahydroxyflavone	antineoplastic agent; antioxidant; plant metabolite
3',4',7-trihydroxyflavone 3',4',7-trihydroxyflavone: from the Sudanese medicinal plant Albizia zygia; structure in first source	2.11	1	0	flavones
lead Lead: A soft, grayish metal with poisonous salts; atomic number 82, atomic weight 207.2, symbol Pb.	5.05	2	1	carbon group element atom; elemental lead; metal atom	neurotoxin
bay 11-7085 BAY11-7085 : A sulfone that is benzene substituted by [(E)-2-cyanoethenyl]sulfonyl and tert-butyl groups at position 1 and 4, respectively. It is an irreversible inhibitor of IkappaB-alpha phosphorylation in cells (IC50 = 10 muM) and prevents the activation of NF-kappaB.	2.17	1	0	benzenes; nitrile; sulfone	anti-inflammatory agent; antibacterial agent; antineoplastic agent; apoptosis inducer; autophagy inducer; EC 2.7.11.10 (IkappaB kinase) inhibitor; ferroptosis inducer; NF-kappaB inhibitor
muconic acid muconic acid: a metabolite of benzene; reported to be a reliable indicator of occupational exposure to benzene; structure given in first source. trans,trans-muconic acid : The trans,trans-isomer of muconic acid. It is metabolite of benzene in humans and serves as a biomarker of occupational exposure to benzene.. muconic acid : A hexadienedioic acid with unsaturation at positions 2 and 4.	8.57	8	0	muconic acid	biomarker; human xenobiotic metabolite
furanoheliangolide furanoheliangolide: structure in first source	2.17	1	0
aluminum Aluminum: A metallic element that has the atomic number 13, atomic symbol Al, and atomic weight 26.98.	7.76	3	0	boron group element atom; elemental aluminium; metal atom
methyl oleate [no description available]	2.06	1	0	fatty acid methyl ester
costunolide [no description available]	6.99	1	0
n-(4-hydroxy-beta-phenethyl)-4-hydroxycinnamide trans-N-p-coumaroyl tyramine: from the twigs of Celtis chinensis; structure in first source	2.05	1	0	hydroxycinnamic acid	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.	3.15	5	0	monocarboxylic acid anion	Saccharomyces cerevisiae metabolite
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	5.25	2	1	cysteinium	fundamental metabolite
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.	7.25	1	0	monoatomic phosphorus; nonmetal atom; pnictogen	macronutrient
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	3.02	4	0
nitecapone nitecapone: structure given in first source	1.97	1	0	hydroxycinnamic acid
artepillin c artepillin C: RN refers to (E)-isomer	2.15	1	0
cefepime Cefepime: A fourth-generation cephalosporin antibacterial agent that is used in the treatment of infections, including those of the abdomen, urinary tract, respiratory tract, and skin. It is effective against PSEUDOMONAS AERUGINOSA and may also be used in the empiric treatment of FEBRILE NEUTROPENIA.. cefepime : A cephalosporin bearing (1-methylpyrrolidinium-1-yl)methyl and (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido groups at positions 3 and 7, respectively, of the cephem skeleton.	5.09	1	1	cephalosporin; oxime O-ether	antibacterial drug
guajavarin guajavarin: from leaves of Psidium guajava	2.11	1	0
narcissin flavonol narcissin flavonol: flavanol glycoside from Strumpfia maritima; do not confuse with other narcissin in Chemline, an alkaloid (lycorine (NM))	2.49	2	0	disaccharide derivative; glycosyloxyflavone; monomethoxyflavone; trihydroxyflavone
lespenefril lespenefril: RN given refers to (L)-isomer. kaempferol 3,7-di-O-alpha-L-rhamnoside : A glycosyloxyflavone that is kaempferol attached to alpha-L-rhamnopyranosyl residues at positions 3 and 7 respectively via glycosidic linkages. It has been isolated from the aerial parts of Vicia faba and Lotus edulis.	2.08	1	0	alpha-L-rhamnoside; dihydroxyflavone; glycosyloxyflavone; monosaccharide derivative; polyphenol	anti-inflammatory agent; antidepressant; antineoplastic agent; apoptosis inducer; bone density conservation agent; hypoglycemic agent; immunomodulator; plant metabolite
3,8-dihydroxy-6h-dibenzo(b,d)pyran-6-one 3,8-dihydroxy-6H-dibenzo(b,d)pyran-6-one: metabolite of ellagic acid	2.05	1	0	coumarins	geroprotector
vitexin rhamnoside vitexin rhamnoside: an apigenin	2.1	1	0	flavonoids; glycoside
alpinumisoflavone alpinumisoflavone: extract from twigs of poisonous British plant	2.06	1	0	isoflavanones	metabolite
carbocyanines Carbocyanines: Compounds that contain three methine groups. They are frequently used as cationic dyes used for differential staining of biological materials.	2.04	1	0	cyanine dye; organic iodide salt	fluorochrome
quercetin-3'-o-beta-d-glucopyranoside quercetin 3'-O-glucoside: structure in first source	2.21	1	0
n-tert-butyl-(2-sulfophenyl)nitrone N-tert-butyl-(2-sulfophenyl)nitrone: Neuroprotectant	2	1	0
benzyl caffeate benzyl caffeate: isolated from Liaoxi propolis	2.21	1	0
su 1498 SU 1498: structure in first source. SU1498 : A monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2E)-2-cyano-3-[4-hydroxy-3,5-di(propan-2-yl)phenyl]prop-2-enoic acid with the amino group of 3-phenylpropylamine.	2.08	1	0	enamide; monocarboxylic acid amide; nitrile; phenols; secondary carboxamide	vascular endothelial growth factor receptor antagonist
bisabolol bisabolol: monocyclic sesquiterpene alcohol with strong bacteriocidal effects, especilly against M. Tuberc.; isolated from seed plant Populus tacamacaha; RN given refers to cpd without isomeric desigation	7.06	1	0
ma-1 tipiracil: inhibits thymidine phosphorylase. tipiracil : A member of the class of pyrimidones that is uracil substituted by chloro and (2-iminopyrrolidin-1-yl)methyl groups at positions 5 and 6 respectively. Used (as the hydrochloride salt) in combination with trifluridine, a nucleoside metabolic inhibitor, for treatment of advanced/relapsed unresectable colorectal cancer.	5.09	1	1	carboxamidine; organochlorine compound; pyrimidone; pyrrolidines	antineoplastic agent; EC 2.4.2.4 (thymidine phosphorylase) inhibitor
ginkgolide b [no description available]	2.08	1	0
tetrodotoxin Tetrodotoxin: An aminoperhydroquinazoline poison found mainly in the liver and ovaries of fishes in the order TETRAODONTIFORMES, which are eaten. The toxin causes paresthesia and paralysis through interference with neuromuscular conduction.. tetrodotoxin : A quinazoline alkaloid that is a marine toxin isolated from fish such as puffer fish. It has been shown to exhibit potential neutotoxicity due to its ability to block voltage-gated sodium channels.	2.04	1	0	azatetracycloalkane; oxatetracycloalkane; quinazoline alkaloid	animal metabolite; bacterial metabolite; marine metabolite; neurotoxin; voltage-gated sodium channel blocker
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.	2.15	1	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.	2.1	1	0
columbianadin columbianadin: furanocoumarin isolated from Peucedanum palustre; RN given refers to columbianadin, (S-(Z))-isomer. columbianadin : An alpha,beta-unsaturated carboxylic ester obtained by formal condensation of the carboxy group of angelic acid with the hydroxy group of 2-[(8S)-2-oxo-8,9-dihydro-2H-furo[2,3-h][1]benzopyran-8-yl]propan-2-ol.	2.07	1	0	alpha,beta-unsaturated carboxylic ester; furanocoumarin	anti-inflammatory agent; antineoplastic agent; apoptosis inducer; hepatoprotective agent; plant metabolite; rat metabolite
mofegiline [no description available]	2	1	0
kyn 54 KYN 54: structure given in first source; a novel synthesized retinoid; potential chemopreventive agent for intestinal neoplasm	2	1	0
(10)-shogaol (10)-shogaol: isolated from ginger; structure in first source	3.25	1	0	enone; monomethoxybenzene; phenols
hydroxysafflor yellow a hydroxysafflor yellow A: from Carthamus tinctorius; structure given in first source. hydroxysafflor yellow A : A C-glycosyl compound that is 3,4,5-trihydroxycyclohexa-2,5-dien-1-one which is substituted by beta-D-glucosyl groups at positions 2 and 4, and by a p-hydroxycinnamoyl group at position 6. It is the main bioactive compound of a traditional Chinese medicine obtained from safflower (Carthamus tinctorius).	2.05	1	0
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	3.17	5	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
alpha-cyperone alpha-cyperone: isolated from the rhizomes of Cyperus rotundus; structure in first source	2.07	1	0
quercetin-3-o-galactoside-7-o-glucoside quercetin-3-O-galactoside-7-O-glucoside: isolated from the seeds of Cuscuta chinensis	2.06	1	0
4,5-di-O-caffeoylquinic acid [no description available]	2.48	2	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.	3	4	0
4-isopropylbenzaldehyde thiosemicarbazone 4-isopropylbenzaldehyde thiosemicarbazone: structure in first source	2.03	1	0
beta-escin Escin: Pentacyclic triterpene saponins, biosynthesized from protoaescigenin and barringtogenol, occurring in the seeds of AESCULUS. It inhibits edema formation and decreases vascular fragility.	2.17	1	0	triterpenoid saponin
methyl chlorogenate methyl chlorogenate: from Eriobotrya japonica; structure in first source	3.01	4	0	quinic acid
isoacteoside isoacteoside: a phenylethanoid glycoside isolated from Indian paintbrush (Verbenaceae) Castilleja linariaefolia; also in other plants; structure given in first source	2.05	1	0	hydroxycinnamic acid
beta-escin [no description available]	2.5	2	0
3-hydroxy-4-methoxybenzaldehyde thiosemicarbazone 3-hydroxy-4-methoxybenzaldehyde thiosemicarbazone: inhibits cabbage butterfly larvae phenoloxidase; structure in first source	2.03	1	0
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
isoborneol isoborneol: RN given refers to cpd without isomeric designation; structure	2.8	3	0	borneol
epigallocatechin-3-o-(3''-o-methyl)-gallate [no description available]	2.05	1	0	catechin
bimosiamose bimosiamose: a selectin inhibitor	2.03	1	0
bicyclol bicyclol: an antihepatitis drug, on the metabolism and hepatotoxicity of aflatoxin B1 (AFB1) in rats.	2.05	1	0
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).	5.82	6	1	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
zeolites [no description available]	5.09	1	1
kaempferol 7-o-glucoside kaempferol 7-O-glucoside: structure in first source. kaempferol 7-O-beta-D-glucopyranoside : A kaempferol O-glucoside that is kaempferol attached to a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	2.02	1	0	beta-D-glucoside; flavonols; kaempferol O-glucoside; monosaccharide derivative; trihydroxyflavone	metabolite; plant metabolite; radical scavenger
artenimol artenimol: derivative of antimalarial drug artemisinin (quinghaosu)	2.11	1	0
alpha-synuclein alpha-Synuclein: A synuclein that is a major component of LEWY BODIES and plays a role in SYNUCLEINOPATHIES, neurodegeneration and neuroprotection.	7.5	2	0
corchoionoside c corchoionoside C: structure given in first source; from leaves of Corchorus olitorius	2.11	1	0
glucosyringic acid [no description available]	2.06	1	0
isosilybin b [no description available]	2.05	1	0
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.	5.06	2	1	alpha-D-glucosyl-(1->4)-D-mannopyranose
isosilybin a isosilybin A: has antineoplastic activity; structure in first source	2.05	1	0
regorafenib [no description available]	5.09	1	1	(trifluoromethyl)benzenes; aromatic ether; monochlorobenzenes; monofluorobenzenes; phenylureas; pyridinecarboxamide	antineoplastic agent; hepatotoxic agent; tyrosine kinase inhibitor
fg-4592 roxadustat: structure in first source. roxadustat : An N-acylglycine resulting from the formal condensation of the amino group of glycine with the carboxy group of 4-hydroxy-1-methyl-7-phenoxyisoquinoline-3-carboxylic acid. It is an inhibitor of hypoxia inducible factor prolyl hydroxylase (HIF-PH).	2.31	1	0	aromatic ether; isoquinolines; N-acylglycine	EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor; EC 1.14.11.29 (hypoxia-inducible factor-proline dioxygenase) inhibitor
ks370g KS370G: antihyperglycemic; structure in first source	2.21	1	0
petrobactin petrobactin: a photoreactive siderophore produced by the oil-degrading marine bacterium; structure in first source	2.04	1	0
syringaresinol, (1r-(1alpha, 3aalpha,4alpha,6aalpha))-isomer (-)-syringaresinol : The (7beta,7'beta,8beta,8'beta)-stereoisomer of syringaresinol.	2.15	1	0	syringaresinol
(+)-dehydrodiconiferyl alcohol (+)-dehydrodiconiferyl alcohol : A dehydrodiconiferyl alcohol that has (2S,3R)-configuration. A natural product isolated from several plant species including Allium sativum and Codonopsis pilosula.	2.05	1	0	dehydrodiconiferyl alcohol	antioxidant; plant metabolite
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.	2.13	1	0
odoratin odoratin: structure; RN given refers to cpd without isomeric designation	2.15	1	0
cleomiscosin d cleomiscosin D: from the root bark of Hibiscus syriacus (Malvaceae); structure in first source	2.13	1	0
peonidin 3-glucoside peonidin 3-glucoside: the methylated form of cyanidin 3-glucoside	2.31	1	0
15-deoxygoyazensolide 15-deoxygoyazensolide: an NSAID with schistossomicidal and trypanosomicidal activities; structure in first source	2.17	1	0
lyoniside lyoniside: see also eleutherosides & syringin for eleutheroside B: 118-34-3; RN given refers to (3beta)-isomer	3.33	6	0
friedelane friedelane: from leaves of Maytenus aquifolium (Celastraceae); structure in first source. friedelane : A triterpene that is docosahydropicene substituted by 8 methyl groups at positions 2, 2, 4a, 6a, 8a, 9, 12b and 14a.	2.05	1	0	triterpene	metabolite
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.	5.08	15	0
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	2.74	3	0	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
tannins gallotannin : A class of hydrolysable tannins obtained by condensation of the carboxy group of gallic acid (and its polymeric derivatives) with the hydroxy groups of a monosaccharide (most commonly glucose).	2.48	2	0	tannin
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.	4.55	7	0
cellulose DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.	1.98	1	0	glycoside
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)	2.15	1	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.	2.17	1	0	chlorophyll; methyl ester	cofactor
sphingosine kinase [no description available]	2.15	1	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.	2.06	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.	2.85	3	0
chitosan [no description available]	3.97	10	0
alpha-pyrone-4,6-dicarboxylic acid alpha-pyrone-4,6-dicarboxylic acid: structure. 2-oxo-2H-pyran-4,6-dicarboxylate : A dicarboxylic acid dianion obtained via deprotonation of both carboxy groups of 2-oxo-2H-pyran-4,6-dicarboxylic acid; major species at pH 7.3.	2.73	3	0	dicarboxylic acid dianion
balanophonin balanophonin: from fruit wall of Cirsium vulgare; structure in first source	2.05	1	0
muconolactone muconolactone: RN given refers to unlabeled parent cpd; structure given in first source. 5-oxo-2,5-dihydro-2-furylacetate : A monocarboxylic acid anion that is the conjugate base of 5-oxo-2,5-dihydro-2-furylacetic acid, formed via deprotonation of the carboxy group; major species at pH 7.3.	2.13	1	0	monocarboxylic acid anion
sodium bisulfite sodium bisulfite: has been used externally for parasitic skin diseases and as gastrointestinal antiseptic; structure. sodium hydrogensulfite : An inorganic sodium salt having hydrogensulfite as the counterion.	2.06	1	0	inorganic sodium salt; sulfite salt	allergen; food antioxidant; food colour retention agent; mutagen; reducing agent
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.	7.41	1	0	monosodium glutamate	flavouring agent
liriodendrin liriodendrin: 573-33-4 is liriodendrin; from bark of Plumeria rubra; structure given in first source	7.03	1	0
s-adenosylmethionine (R)-S-adenosyl-L-methionine : An S-adenosyl-L-methionine that has R-configuration.. S-adenosyl-L-methionine zwitterion : A zwitterionic tautomer of S-adenosyl-L-methionine arising from shift of the proton from the carboxy group to the amino group.. (R)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has R-configuration; major species at pH 7.3.. (S)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has S-configuration; major species at pH 7.3.. S-adenosyl-L-methionine : A sulfonium compound that is the S-adenosyl derivative of L-methionine. It is an intermediate in the metabolic pathway of methionine.	3.81	4	0	organic cation; sulfonium compound	coenzyme; cofactor; human metabolite; micronutrient; Mycoplasma genitalium metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
albiflorin albiflorin: glucoside in peony roots. albiflorin : A monoterpene glycoside with formula C23H28O11, originally isolated from the roots of Paeonia lactiflora.	2.15	1	0	benzoate ester; beta-D-glucoside; bridged compound; gamma-lactone; monoterpene glycoside; secondary alcohol	neuroprotective agent; plant metabolite
mannans [no description available]	2.15	1	0
nitrogenase Nitrogenase: An enzyme system that catalyzes the fixing of nitrogen in soil bacteria and blue-green algae (CYANOBACTERIA). EC 1.18.6.1.	2.03	1	0
10-nonacosanol 10-nonacosanol: from the root of Euphorbia ebracteolata. nonacosan-10-ol : A fatty alcohol that is nonacosane substituted by a hydroxy group at position 10.	2.05	1	0	secondary fatty alcohol; ultra-long-chain fatty alcohol	plant metabolite
prunin prunin: structure in first source	2.1	1	0
piperidines Piperidines: A family of hexahydropyridines.	2.21	1	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.	3.01	4	0
4-hydroxymellein 4-hydroxymellein: alpha-Glucosidase Inhibitor from Xylaria feejeensis associated with Hintonia latiflora; structure in first source. 4-hydroxymellein : An isochromane that is mellein bearing a hydroxy group at position 4.	2.13	1	0
typhaneoside typhaneoside: isolated from pollen of Typha angustfolia L. (puhuang); structure given in first source	2.21	1	0	flavonoids; glycoside
peoniflorin [no description available]	2.07	1	0
isoquercitrin [no description available]	2.98	4	0
heme Heme: The color-furnishing portion of hemoglobin. It is found free in tissues and as the prosthetic group in many hemeproteins.. ferroheme : Any iron(II)--porphyrin coordination complex.. ferroheme b : Heme b in which the iron has oxidation state +2.. heme : A heme is any tetrapyrrolic chelate of iron.	2.02	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.	3.67	9	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.	2.06	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.	2.05	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.	2.15	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.	4.83	10	0	monohydroxybenzoate	plant metabolite
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.	3.85	11	0	benzenes; hydroxycoumarin; methyl ketone
6-o-palmitoylascorbic acid [no description available]	2.11	1	0	fatty acid ester
4-hydroxycoumarin 2-hydroxychromone: structure	2.15	1	0	hydroxycoumarin
clorobiocin clorobiocin: chlorine-containing antibiotic related to novobiocin	2.06	1	0
enramycin enramycin: isolated from cultures of Streptomyces fungicidicus	2.21	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.	7.25	1	0	ketal
pyrethrins [no description available]	2.17	1	0
stigmasterol glucoside stigmasterol glucoside: toxic component of Cycas circinalis seeds possibly etiologic in Guamanian ALS-parkinsonism-dementia complex; structure in first source	2.01	1	0	steroid
pravastatin acanthoside D: from Salsola collina	2.1	1	0	glycoside; lignan
cyclin d1 Cyclin D1: Protein encoded by the bcl-1 gene which plays a critical role in regulating the cell cycle. Overexpression of cyclin D1 is the result of bcl-1 rearrangement, a t(11;14) translocation, and is implicated in various neoplasms.	2.05	1	0
ginkgolide b [no description available]	7.25	1	0
peoniflorin peoniflorin: from Radix and of Paeonia suffruticosa	3.05	4	0
flavin mononucleotide Flavin Mononucleotide: A coenzyme for a number of oxidative enzymes including NADH DEHYDROGENASE. It is the principal form in which RIBOFLAVIN is found in cells and tissues.	2.15	1	0
neohesperidin [no description available]	2.25	1	0
agathic acid agathic acid: labdane; RN given for (1S-(1alpha,4aalpha,5alpha(E),8abeta))-isomer; metabolite of isocupressic acid; structure in first source	2.17	1	0
deoxyguanosine [no description available]	2.45	2	0	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
guanosine diphosphate Guanosine Diphosphate: A guanine nucleotide containing two phosphate groups esterified to the sugar moiety.	2.02	1	0	guanosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	Escherichia coli metabolite; mouse metabolite; uncoupling protein inhibitor
hypoxanthine [no description available]	2.01	1	0	nucleobase analogue; oxopurine; purine nucleobase	fundamental metabolite
inosine [no description available]	2.11	1	0	inosines; purines D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae 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.	7.76	3	0	folic acids; N-acyl-amino acid	human metabolite; mouse metabolite; nutrient
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)	2.7	3	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
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.	2.94	4	0	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger
2,4-diaminohypoxanthine 2,4-diaminohypoxanthine: do not confuse abbreviation DAHP with various dehydro-deoxy-arabino-heptulosonic acid phosphates which also use DAHP; RN given refers to parent cpd; structure	2.06	1	0	hydroxypyrimidine
sildenafil citrate Sildenafil Citrate: A PHOSPHODIESTERASE TYPE-5 INHIBITOR; VASODILATOR AGENT and UROLOGICAL AGENT that is used in the treatment of ERECTILE DYSFUNCTION and PRIMARY PULMONARY HYPERTENSION.. sildenafil citrate : The citrate salt of sildenafil.	2.08	1	0	citrate salt	EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor; vasodilator agent
vardenafil dihydrochloride Vardenafil Dihydrochloride: A piperazine derivative, PHOSPHODIESTERASE 5 INHIBITOR and VASODILATOR AGENT that is used as a UROLOGICAL AGENT in the treatment of ERECTILE DYSFUNCTION.	2.08	1	0
salicylaldehyde thiosemicarbazone salicylaldehyde thiosemicarbazone: structure given in first source	2.03	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	1.98	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.	2.45	2	0	guanosines	biomarker
galloflavin galloflavin: structure in first source	2.13	1	0
cyanine dye 3 cyanine dye 3: structures of Cy3 derivatives given in first source	2.04	1	0
maltodextrin maltodextrin : A dextrin in which the D-glucose units are linked by alpha-(1->4) glycosidic bonds.	2.13	1	0
phosphorus radioisotopes Phosphorus Radioisotopes: Unstable isotopes of phosphorus that decay or disintegrate emitting radiation. P atoms with atomic weights 28-34 except 31 are radioactive phosphorus isotopes.	2.01	1	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.	2.1	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.	3.53	8	0

Condition	Relationship Strength	Studies	Trials
Complications of Diabetes Mellitus [description not available]	2.77	3	0
Cataract, Membranous [description not available]	2.04	1	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)	2.04	1	0
B16 Melanoma [description not available]	2.77	3	0
Innate Inflammatory Response [description not available]	7.56	27	1
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.	7.56	27	1
Blood Pressure, High [description not available]	2.8	3	0
Hypertension Persistently high systemic arterial BLOOD PRESSURE. Based on multiple readings (BLOOD PRESSURE DETERMINATION), hypertension is currently defined as when SYSTOLIC PRESSURE is consistently greater than 140 mm Hg or when DIASTOLIC PRESSURE is consistently 90 mm Hg or more.	2.8	3	0
Bancroftian Elephantiasis [description not available]	2.07	1	0
Elephantiasis, Filarial Parasitic infestation of the human lymphatic system by WUCHERERIA BANCROFTI or BRUGIA MALAYI. It is also called lymphatic filariasis.	2.07	1	0
Angiogenesis, Pathologic [description not available]	2.52	2	0
Cochlear Hearing Loss [description not available]	2.15	1	0
Nodular Goiter [description not available]	2.15	1	0
Goiter, Nodular An enlarged THYROID GLAND containing multiple nodules (THYROID NODULE), usually resulting from recurrent thyroid HYPERPLASIA and involution over many years to produce the irregular enlargement. Multinodular goiters may be nontoxic or may induce THYROTOXICOSIS.	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.	2.15	1	0
Scurf [description not available]	2.15	1	0
Dandruff Excessive shedding of dry scaly material from the scalp in humans.	2.15	1	0
Degenerative Diseases, Central Nervous System [description not available]	6.45	5	1
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.	11.45	5	1
Tauopathies Neurodegenerative disorders involving deposition of abnormal tau protein isoforms (TAU PROTEINS) in neurons and glial cells in the brain. Pathological aggregations of tau proteins are associated with mutation of the tau gene on chromosome 17 in patients with ALZHEIMER DISEASE; DEMENTIA; PARKINSONIAN DISORDERS; progressive supranuclear palsy (SUPRANUCLEAR PALSY, PROGRESSIVE); and corticobasal degeneration.	2.21	1	0
Protein Aggregation, Pathological A biochemical phenomenon in which misfolded proteins aggregate either intra- or extracellularly. Triggered by factors such as MUTATION; POST-TRANSLATIONAL MODIFICATIONS, and environmental stress, it is generally associated with ALZHEIMER DISEASE; PARKINSON DISEASE; HUNTINGTON DISEASE; and TYPE 2 DIABETES MELLITUS.	2.21	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.	7.82	2	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.	2.82	2	0
Lung Injury, Acute [description not available]	2.82	3	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).	2.82	3	0
Complex Regional Pain Syndrome [description not available]	2.31	1	0
Anoxemia [description not available]	2.96	4	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	10.82	50	4
Allodynia [description not available]	7.76	2	0
Nerve Pain [description not available]	2.76	2	0
Hypoxia Sub-optimal OXYGEN levels in the ambient air of living organisms.	2.96	4	0
Neuralgia Intense or aching pain that occurs along the course or distribution of a peripheral or cranial nerve.	2.76	2	0
Complex Regional Pain Syndromes Conditions characterized by pain involving an extremity or other body region, HYPERESTHESIA, and localized autonomic dysfunction following injury to soft tissue or nerve. The pain is usually associated with ERYTHEMA; SKIN TEMPERATURE changes, abnormal sudomotor activity (i.e., changes in sweating due to altered sympathetic innervation) or edema. The degree of pain and other manifestations is out of proportion to that expected from the inciting event. Two subtypes of this condition have been described: type I; (REFLEX SYMPATHETIC DYSTROPHY) and type II; (CAUSALGIA). (From Pain 1995 Oct;63(1):127-33)	2.31	1	0
Eczema, Atopic [description not available]	2.31	1	0
Dermatitis, Atopic A chronic inflammatory genetically determined disease of the skin marked by increased ability to form reagin (IgE), with increased susceptibility to allergic rhinitis and asthma, and hereditary disposition to a lowered threshold for pruritus. It is manifested by lichenification, excoriation, and crusting, mainly on the flexural surfaces of the elbow and knee. In infants it is known as infantile eczema.	2.31	1	0
Cancer of Colon [description not available]	8.18	9	4
Colonic Neoplasms Tumors or cancer of the COLON.	8.18	9	4
Acute Confusional Senile Dementia [description not available]	8.6	10	4
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)	8.6	10	4
Infections, Orthomyxoviridae [description not available]	2.58	2	0
Orthomyxoviridae Infections Virus diseases caused by the ORTHOMYXOVIRIDAE.	2.58	2	0
Brain Disorders [description not available]	2.51	2	0
Brain Diseases Pathologic conditions affecting the BRAIN, which is composed of the intracranial components of the CENTRAL NERVOUS SYSTEM. This includes (but is not limited to) the CEREBRAL CORTEX; intracranial white matter; BASAL GANGLIA; THALAMUS; HYPOTHALAMUS; BRAIN STEM; and CEREBELLUM.	2.51	2	0
Acute Brain Injuries [description not available]	2.98	4	0
Anterior Choroidal Artery Infarction [description not available]	2.41	1	0
Cerebral Ischemia [description not available]	8	4	0
Injury, Ischemia-Reperfusion [description not available]	5.94	8	1
Brain Injuries Acute and chronic (see also BRAIN INJURIES, CHRONIC) injuries to the brain, including the cerebral hemispheres, CEREBELLUM, and BRAIN STEM. Clinical manifestations depend on the nature of injury. Diffuse trauma to the brain is frequently associated with DIFFUSE AXONAL INJURY or COMA, POST-TRAUMATIC. Localized injuries may be associated with NEUROBEHAVIORAL MANIFESTATIONS; HEMIPARESIS, or other focal neurologic deficits.	2.98	4	0
Cerebral Infarction The formation of an area of NECROSIS in the CEREBRUM caused by an insufficiency of arterial or venous blood flow. Infarcts of the cerebrum are generally classified by hemisphere (i.e., left vs. right), lobe (e.g., frontal lobe infarction), arterial distribution (e.g., INFARCTION, ANTERIOR CEREBRAL ARTERY), and etiology (e.g., embolic infarction).	2.41	1	0
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.	3	4	0
Reperfusion Injury Adverse functional, metabolic, or structural changes in tissues that result from the restoration of blood flow to the tissue (REPERFUSION) following ISCHEMIA.	5.94	8	1
Anasarca [description not available]	3.18	5	0
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	8.18	5	0
Acute Post-Traumatic Stress Disorder [description not available]	2.41	1	0
Stress Disorders, Post-Traumatic A class of traumatic stress disorders with symptoms that last more than one month.	2.41	1	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	3.84	11	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.	10.48	4	1
Experimental Hepatoma [description not available]	2.76	3	0
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	10.35	12	9
Alloxan Diabetes [description not available]	4.84	11	0
Chronic Hepatitis B [description not available]	2.41	1	0
Hepatitis B Virus Infection [description not available]	2.41	1	0
Hepatitis B INFLAMMATION of the LIVER in humans caused by a member of the ORTHOHEPADNAVIRUS genus, HEPATITIS B VIRUS. It is primarily transmitted by parenteral exposure, such as transfusion of contaminated blood or blood products, but can also be transmitted via sexual or intimate personal contact.	2.41	1	0
Hepatitis B, Chronic INFLAMMATION of the LIVER in humans caused by HEPATITIS B VIRUS lasting six months or more. It is primarily transmitted by parenteral exposure, such as transfusion of contaminated blood or blood products, but can also be transmitted via sexual or intimate personal contact.	2.41	1	0
Diabetes Mellitus, Adult-Onset [description not available]	3.47	5	0
Insulin Sensitivity [description not available]	6.27	10	1
Diabetes Mellitus, Type 2 A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.	3.47	5	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.	6.27	10	1
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).	10.5	4	1
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	8.11	4	0
Cardiovascular Stroke [description not available]	2.97	4	0
Myocardial Infarction NECROSIS of the MYOCARDIUM caused by an obstruction of the blood supply to the heart (CORONARY CIRCULATION).	2.97	4	0
Deficiency, Thiamine [description not available]	2.6	1	0
Korsakoff Psychosis [description not available]	2.6	1	0
Thiamine Deficiency A nutritional condition produced by a deficiency of THIAMINE in the diet, characterized by anorexia, irritability, and weight loss. Later, patients experience weakness, peripheral neuropathy, headache, and tachycardia. In addition to being caused by a poor diet, thiamine deficiency in the United States most commonly occurs as a result of alcoholism, since ethanol interferes with thiamine absorption. In countries relying on polished rice as a dietary staple, BERIBERI prevalence is very high. (From Cecil Textbook of Medicine, 19th ed, p1171)	7.6	1	0
Acute Kidney Failure [description not available]	2.66	2	0
Acute Kidney Injury Abrupt reduction in kidney function. Acute kidney injury encompasses the entire spectrum of the syndrome including acute kidney failure; ACUTE KIDNEY TUBULAR NECROSIS; and other less severe conditions.	2.66	2	0
Breast Cancer [description not available]	2.53	2	0
Animal Mammary Carcinoma [description not available]	2.6	1	0
Breast Neoplasms Tumors or cancer of the human BREAST.	2.53	2	0
Cirrhosis [description not available]	2.72	2	0
Cardiac Failure [description not available]	3.01	2	0
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	7.72	2	0
Heart Failure A heterogeneous condition in which the heart is unable to pump out sufficient blood to meet the metabolic need of the body. Heart failure can be caused by structural defects, functional abnormalities (VENTRICULAR DYSFUNCTION), or a sudden overload beyond its capacity. Chronic heart failure is more common than acute heart failure which results from sudden insult to cardiac function, such as MYOCARDIAL INFARCTION.	8.01	2	0
Bowel Diseases, Inflammatory [description not available]	5.31	2	1
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.	3.01	3	0
Inflammatory Bowel Diseases Chronic, non-specific inflammation of the GASTROINTESTINAL TRACT. Etiology may be genetic or environmental. This term includes CROHN DISEASE and ULCERATIVE COLITIS.	5.31	2	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.	5.31	2	1
Colitis Gravis [description not available]	2.63	2	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.	2.63	2	0
Mastitis INFLAMMATION of the BREAST, or MAMMARY GLAND.	7.6	1	0
Genetic Predisposition [description not available]	4.91	1	1
Cholangiocellular Carcinoma [description not available]	4.91	1	1
Blood Poisoning [description not available]	10.08	11	9
Apnea, Obstructive Sleep [description not available]	4.92	2	1
Airflow Obstruction, Chronic [description not available]	8.03	4	4
Malnourishment [description not available]	4.91	1	1
DDPAC [description not available]	4.91	1	1
Cognitive Decline [description not available]	5.02	2	1
Fatty Liver, Nonalcoholic [description not available]	5.84	3	1
2019 Novel Coronavirus Disease [description not available]	4.91	1	1
Adenocarcinoma, Basal Cell [description not available]	5.23	4	1
ALS - Amyotrophic Lateral Sclerosis [description not available]	5.09	3	1
Asthma, Bronchial [description not available]	5.39	4	1
Bacterial Disease [description not available]	4.91	1	1
Bile Duct Cancer [description not available]	4.91	1	1
Bone Cancer [description not available]	4.91	1	1
African Lymphoma [description not available]	4.91	1	1
Campylobacter Infection [description not available]	8.03	4	4
Carcinoma, Epidermoid [description not available]	5.22	4	1
Vibrio cholerae Infection [description not available]	4.91	1	1
Cancer of Esophagus [description not available]	4.9	2	1
Esophagitis, Reflux [description not available]	4.91	1	1
Exanthem [description not available]	4.91	1	1
Cholera Infantum [description not available]	4.91	1	1
Cancer of Gastrointestinal Tract [description not available]	4.91	1	1
Female Genital Neoplasms [description not available]	4.91	1	1
Hepatitis, Viral, Non-A, Non-B, Parenterally-Transmitted [description not available]	4.91	1	1
Hepatocellular Carcinoma [description not available]	5.67	6	1
Leukocytopenia [description not available]	4.91	1	1
Cirrhosis, Liver [description not available]	5.27	3	1
Cancer of Liver [description not available]	5.76	7	1
Metaplasia A condition in which there is a change of one adult cell type to another similar adult cell type.	4.91	1	1
MS (Multiple Sclerosis) [description not available]	4.91	1	1
Cardiomyopathies, Primary [description not available]	4.91	1	1
Benign Neoplasms [description not available]	5.78	4	1
Ache [description not available]	8.17	7	4
Cancer of Pancreas [description not available]	11.85	16	16
Complication, Postoperative [description not available]	4.92	2	1
Embolism, Pulmonary [description not available]	4.91	1	1
Cancer of Rectum [description not available]	8.03	4	4
Breathing Sounds [description not available]	4.91	1	1
Osteogenic Sarcoma [description not available]	4.91	1	1
Endotoxin Shock [description not available]	4.91	1	1
Cancer of Skin [description not available]	5.03	3	1
Cancer of the Thyroid [description not available]	4.91	1	1
Colorectal Cancer [description not available]	5.76	3	1
Critical Illness A disease or state in which death is possible or imminent.	4.91	1	1
Carcinoma, Ductal, Pancreatic [description not available]	4.91	1	1
Hoarseness An unnaturally deep or rough quality of voice.	4.91	1	1
Bronchospasm, Exercise-Induced [description not available]	4.91	1	1
Delayed Effects, Prenatal Exposure [description not available]	4.91	1	1
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	5.23	4	1
Alcohol Drinking Behaviors associated with the ingesting of ALCOHOLIC BEVERAGES, including social drinking.	4.91	1	1
Amyotrophic Lateral Sclerosis A degenerative disorder affecting upper MOTOR NEURONS in the brain and lower motor neurons in the brain stem and SPINAL CORD. Disease onset is usually after the age of 50 and the process is usually fatal within 3 to 6 years. Clinical manifestations include progressive weakness, atrophy, FASCICULATION, hyperreflexia, DYSARTHRIA, dysphagia, and eventual paralysis of respiratory function. Pathologic features include the replacement of motor neurons with fibrous ASTROCYTES and atrophy of anterior SPINAL NERVE ROOTS and corticospinal tracts. (From Adams et al., Principles of Neurology, 6th ed, pp1089-94)	5.09	3	1
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).	5.39	4	1
Asthma, Exercise-Induced Asthma attacks following a period of exercise. Usually the induced attack is short-lived and regresses spontaneously. The magnitude of postexertional airway obstruction is strongly influenced by the environment in which exercise is performed (i.e. inhalation of cold air during physical exertion markedly augments the severity of the airway obstruction; conversely, warm humid air blunts or abolishes it).	4.91	1	1
Atrophy Decrease in the size of a cell, tissue, organ, or multiple organs, associated with a variety of pathological conditions such as abnormal cellular changes, ischemia, malnutrition, or hormonal changes.	4.96	2	1
Bacterial Infections Infections by bacteria, general or unspecified.	4.91	1	1
Bile Duct Neoplasms Tumors or cancer of the BILE DUCTS.	4.91	1	1
Bone Neoplasms Tumors or cancer located in bone tissue or specific BONES.	4.91	1	1
Burkitt Lymphoma A form of undifferentiated malignant LYMPHOMA usually found in central Africa, but also reported in other parts of the world. It is commonly manifested as a large osteolytic lesion in the jaw or as an abdominal mass. B-cell antigens are expressed on the immature cells that make up the tumor in virtually all cases of Burkitt lymphoma. The Epstein-Barr virus (HERPESVIRUS 4, HUMAN) has been isolated from Burkitt lymphoma cases in Africa and it is implicated as the causative agent in these cases; however, most non-African cases are EBV-negative.	4.91	1	1
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)	5.22	4	1
Cholera An acute diarrheal disease endemic in India and Southeast Asia whose causative agent is VIBRIO CHOLERAE. This condition can lead to severe dehydration in a matter of hours unless quickly treated.	4.91	1	1
Esophageal Neoplasms Tumors or cancer of the ESOPHAGUS.	4.9	2	1
Esophagitis, Peptic INFLAMMATION of the ESOPHAGUS that is caused by the reflux of GASTRIC JUICE with contents of the STOMACH and DUODENUM.	4.91	1	1
Exanthema Diseases in which skin eruptions or rashes are a prominent manifestation. Classically, six such diseases were described with similar rashes; they were numbered in the order in which they were reported. Only the fourth (Duke's disease), fifth (ERYTHEMA INFECTIOSUM), and sixth (EXANTHEMA SUBITUM) numeric designations survive as occasional synonyms in current terminology.	4.91	1	1
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.	4.91	1	1
Genital Neoplasms, Female Tumor or cancer of the female reproductive tract (GENITALIA, FEMALE).	4.91	1	1
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.	4.91	1	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.	5.67	6	1
Leukopenia A decrease in the number of LEUKOCYTES in a blood sample below the normal range (LEUKOCYTE COUNT less than 4000).	4.91	1	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.	5.27	3	1
Liver Neoplasms Tumors or cancer of the LIVER.	5.76	7	1
Multiple Sclerosis An autoimmune disorder mainly affecting young adults and characterized by destruction of myelin in the central nervous system. Pathologic findings include multiple sharply demarcated areas of demyelination throughout the white matter of the central nervous system. Clinical manifestations include visual loss, extra-ocular movement disorders, paresthesias, loss of sensation, weakness, dysarthria, spasticity, ataxia, and bladder dysfunction. The usual pattern is one of recurrent attacks followed by partial recovery (see MULTIPLE SCLEROSIS, RELAPSING-REMITTING), but acute fulminating and chronic progressive forms (see MULTIPLE SCLEROSIS, CHRONIC PROGRESSIVE) also occur. (Adams et al., Principles of Neurology, 6th ed, p903)	4.91	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).	4.91	1	1
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	5.78	4	1
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	8.17	7	4
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).	11.85	16	16
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.	4.92	2	1
Pulmonary Embolism Blocking of the PULMONARY ARTERY or one of its branches by an EMBOLUS.	4.91	1	1
Rectal Neoplasms Tumors or cancer of the RECTUM.	8.03	4	4
Respiratory Sounds Noises, normal and abnormal, heard on auscultation over any part of the RESPIRATORY TRACT.	4.91	1	1
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)	4.91	1	1
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)	6.11	11	1
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.	4.91	1	1
Skin Neoplasms Tumors or cancer of the SKIN.	5.03	3	1
Thyroid Neoplasms Tumors or cancer of the THYROID GLAND.	4.91	1	1
Colorectal Neoplasms Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.	5.76	3	1
Cholangiocarcinoma A malignant tumor arising from the epithelium of the BILE DUCTS.	4.91	1	1
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.	15.08	11	9
Sleep Apnea, Obstructive A disorder characterized by recurrent apneas during sleep despite persistent respiratory efforts. It is due to upper airway obstruction. The respiratory pauses may induce HYPERCAPNIA or HYPOXIA. Cardiac arrhythmias and elevation of systemic and pulmonary arterial pressures may occur. Frequent partial arousals occur throughout sleep, resulting in relative SLEEP DEPRIVATION and daytime tiredness. Associated conditions include OBESITY; ACROMEGALY; MYXEDEMA; micrognathia; MYOTONIC DYSTROPHY; adenotonsilar dystrophy; and NEUROMUSCULAR DISEASES. (From Adams et al., Principles of Neurology, 6th ed, p395)	4.92	2	1
Carcinoma, Pancreatic Ductal Carcinoma that arises from the PANCREATIC DUCTS. It accounts for the majority of cancers derived from the PANCREAS.	4.91	1	1
Pulmonary Disease, Chronic Obstructive A disease of chronic diffuse irreversible airflow obstruction. Subcategories of COPD include CHRONIC BRONCHITIS and PULMONARY EMPHYSEMA.	8.03	4	4
Malnutrition An imbalanced nutritional status resulting from insufficient intake of nutrients to meet normal physiological requirement.	4.91	1	1
Azoospermia A condition of having no sperm present in the ejaculate (SEMEN).	4.91	1	1
Sarcopenia Progressive decline in muscle mass due to aging which results in decreased functional capacity of muscles.	4.91	1	1
Frontotemporal Dementia The most common clinical form of FRONTOTEMPORAL LOBAR DEGENERATION, this dementia presents with personality and behavioral changes often associated with disinhibition, apathy, and lack of insight.	4.91	1	1
Cognitive Dysfunction Diminished or impaired mental and/or intellectual function.	5.02	2	1
Non-alcoholic Fatty Liver Disease Fatty liver finding without excessive ALCOHOL CONSUMPTION.	5.84	3	1
Polycystic Ovarian Syndrome [description not available]	2.6	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.	7.6	1	0
Ovarian Diseases Pathological processes of the OVARY.	2.82	2	0
Adnexal Torsion [description not available]	2.6	1	0
Abnormality, Torsion [description not available]	2.6	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.	2.6	1	0
Cancer of Prostate [description not available]	2.78	3	0
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	2.78	3	0
Alcoholic Liver Diseases [description not available]	2.21	1	0
Liver Diseases, Alcoholic Liver diseases associated with ALCOHOLISM. It usually refers to the coexistence of two or more subentities, i.e., ALCOHOLIC FATTY LIVER; ALCOHOLIC HEPATITIS; and ALCOHOLIC CIRRHOSIS.	2.21	1	0
Impaired Glucose Tolerance [description not available]	2.21	1	0
Dyslipidemia [description not available]	2.59	2	0
Liver Steatosis [description not available]	2.51	2	0
Hyperglycemia, Postprandial Abnormally high BLOOD GLUCOSE level after a meal.	2.59	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.	2.51	2	0
Hyperglycemia Abnormally high BLOOD GLUCOSE level.	2.59	2	0
Glucose Intolerance A pathological state in which BLOOD GLUCOSE level is less than approximately 140 mg/100 ml of PLASMA at fasting, and above approximately 200 mg/100 ml plasma at 30-, 60-, or 90-minute during a GLUCOSE TOLERANCE TEST. This condition is seen frequently in DIABETES MELLITUS, but also occurs with other diseases and MALNUTRITION.	2.21	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.	2.59	2	0
E coli Infections [description not available]	2.69	2	0
Escherichia coli Infections Infections with bacteria of the species ESCHERICHIA COLI.	2.69	2	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.	2.25	1	0
Autoimmune Diabetes [description not available]	2.54	2	0
Diabetes Mellitus, Type 1 A subtype of DIABETES MELLITUS that is characterized by INSULIN deficiency. It is manifested by the sudden onset of severe HYPERGLYCEMIA, rapid progression to DIABETIC KETOACIDOSIS, and DEATH unless treated with insulin. The disease may occur at any age, but is most common in childhood or adolescence.	2.54	2	0
Atherogenesis [description not available]	4.4	7	0
Atherosclerosis A thickening and loss of elasticity of the walls of ARTERIES that occurs with formation of ATHEROSCLEROTIC PLAQUES within the ARTERIAL INTIMA.	4.4	7	0
Adenoma, Prostatic [description not available]	2.25	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.	7.25	1	0
Rheumatoid Arthritis [description not available]	7.25	1	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.	2.25	1	0
Contact Dermatitis [description not available]	2.73	3	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.	2.73	3	0
Astrocytosis [description not available]	2.25	1	0
Arteriosclerosis, Coronary [description not available]	2.25	1	0
Rodent Diseases Diseases of rodents of the order RODENTIA. This term includes diseases of Sciuridae (squirrels), Geomyidae (gophers), Heteromyidae (pouched mice), Castoridae (beavers), Cricetidae (rats and mice), Muridae (Old World rats and mice), Erethizontidae (porcupines), and Caviidae (guinea pigs).	2.25	1	0
Coronary Artery Disease Pathological processes of CORONARY ARTERIES that may derive from a congenital abnormality, atherosclerotic, or non-atherosclerotic cause.	7.25	1	0
Cognition Disorders Disorders characterized by disturbances in mental processes related to learning, thinking, reasoning, and judgment.	2.87	3	0
Sterility, Male [description not available]	2.25	1	0
Infertility, Male The inability of the male to effect FERTILIZATION of an OVUM after a specified period of unprotected intercourse. Male sterility is permanent infertility.	2.25	1	0
Idiopathic Parkinson Disease [description not available]	2.76	3	0
Parkinson Disease A progressive, degenerative neurologic disease characterized by a TREMOR that is maximal at rest, retropulsion (i.e. a tendency to fall backwards), rigidity, stooped posture, slowness of voluntary movements, and a masklike facial expression. Pathologic features include loss of melanin containing neurons in the substantia nigra and other pigmented nuclei of the brainstem. LEWY BODIES are present in the substantia nigra and locus coeruleus but may also be found in a related condition (LEWY BODY DISEASE, DIFFUSE) characterized by dementia in combination with varying degrees of parkinsonism. (Adams et al., Principles of Neurology, 6th ed, p1059, pp1067-75)	7.76	3	0
Arthritis, Degenerative [description not available]	2.78	3	0
Osteoarthritis A progressive, degenerative joint disease, the most common form of arthritis, especially in older persons. The disease is thought to result not from the aging process but from biochemical changes and biomechanical stresses affecting articular cartilage. In the foreign literature it is often called osteoarthrosis deformans.	2.78	3	0
Brain Swelling [description not available]	2.63	2	0
Brain Hemorrhage, Cerebral [description not available]	2.94	3	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)	7.63	2	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.	2.94	3	0
Cancer of Lung [description not available]	2.74	3	0
Lung Neoplasms Tumors or cancer of the LUNG.	2.74	3	0
Cerebral Infarction, Middle Cerebral Artery [description not available]	2.73	3	0
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.	2.73	3	0
Diabetes Mellitus A heterogeneous group of disorders characterized by HYPERGLYCEMIA and GLUCOSE INTOLERANCE.	3.55	2	0
Chronic Illness [description not available]	2.31	1	0
Chronic Disease Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).	2.31	1	0
Acute Liver Injury, Drug-Induced [description not available]	3.45	7	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.	3.45	7	0
HPV Infection [description not available]	2.31	1	0
Papillomavirus Infections Neoplasms of the skin and mucous membranes caused by papillomaviruses. They are usually benign but some have a high risk for malignant progression.	2.31	1	0
Infections, Staphylococcal [description not available]	2.57	2	0
Staphylococcal Infections Infections with bacteria of the genus STAPHYLOCOCCUS.	2.57	2	0
MODS [description not available]	2.31	1	0
Acute Edematous Pancreatitis [description not available]	2.31	1	0
Multiple Organ Failure A progressive condition usually characterized by combined failure of several organs such as the lungs, liver, kidney, along with some clotting mechanisms, usually postinjury or postoperative.	2.31	1	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.	7.31	1	0
Diabetes Mellitus, Gestational [description not available]	2.31	1	0
Diabetes, Gestational Diabetes mellitus induced by PREGNANCY but resolved at the end of pregnancy. It does not include previously diagnosed diabetics who become pregnant (PREGNANCY IN DIABETICS). Gestational diabetes usually develops in late pregnancy when insulin antagonistic hormones peaks leading to INSULIN RESISTANCE; GLUCOSE INTOLERANCE; and HYPERGLYCEMIA.	2.31	1	0
Malignant Melanoma [description not available]	2.42	2	0
Melanoma A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)	7.42	2	0
Encephalopathy, Traumatic [description not available]	2.15	1	0
Brain Injuries, Traumatic A form of acquired brain injury which occurs when a sudden trauma causes damage to the brain.	2.15	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.	4.21	3	1
Newcastle Disease An acute febrile, contagious, viral disease of birds caused by an AVULAVIRUS called NEWCASTLE DISEASE VIRUS. It is characterized by respiratory and nervous symptoms in fowl and is transmissible to man causing a severe, but transient conjunctivitis.	2.17	1	0
Diabetic Glomerulosclerosis [description not available]	3.7	3	0
Diabetic Nephropathies KIDNEY injuries associated with diabetes mellitus and affecting KIDNEY GLOMERULUS; ARTERIOLES; KIDNEY TUBULES; and the interstitium. Clinical signs include persistent PROTEINURIA, from microalbuminuria progressing to ALBUMINURIA of greater than 300 mg/24 h, leading to reduced GLOMERULAR FILTRATION RATE and END-STAGE RENAL DISEASE.	3.7	3	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.	2.17	1	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.	2.17	1	0
Aura [description not available]	2.17	1	0
Epilepsy A disorder characterized by recurrent episodes of paroxysmal brain dysfunction due to a sudden, disorderly, and excessive neuronal discharge. Epilepsy classification systems are generally based upon: (1) clinical features of the seizure episodes (e.g., motor seizure), (2) etiology (e.g., post-traumatic), (3) anatomic site of seizure origin (e.g., frontal lobe seizure), (4) tendency to spread to other structures in the brain, and (5) temporal patterns (e.g., nocturnal epilepsy). (From Adams et al., Principles of Neurology, 6th ed, p313)	2.17	1	0
Cancer of Ovary [description not available]	2.17	1	0
Ovarian Neoplasms Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.	2.17	1	0
Birnaviridae Infections Virus diseases caused by the BIRNAVIRIDAE.	3.9	2	1
Adverse Drug Event [description not available]	2.21	1	0
Drug-Related Side Effects and Adverse Reactions Disorders that result from the intended use of PHARMACEUTICAL PREPARATIONS. Included in this heading are a broad variety of chemically-induced adverse conditions due to toxicity, DRUG INTERACTIONS, and metabolic effects of pharmaceuticals.	2.21	1	0
Airway Remodeling The structural changes in the number, mass, size and/or composition of the airway tissues.	2.21	1	0
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	2.77	3	0
Injuries, Spinal Cord [description not available]	2.21	1	0
Hematoma, Epidural, Spinal A rare epidural hematoma in the spinal epidural space, usually due to a vascular malformation (CENTRAL NERVOUS SYSTEM VASCULAR MALFORMATIONS) or TRAUMA. Spontaneous spinal epidural hematoma is a neurologic emergency due to a rapidly evolving compressive MYELOPATHY.	2.21	1	0
Spinal Cord Injuries Penetrating and non-penetrating injuries to the spinal cord resulting from traumatic external forces (e.g., WOUNDS, GUNSHOT; WHIPLASH INJURIES; etc.).	2.21	1	0
Depression Depressive states usually of moderate intensity in contrast with MAJOR DEPRESSIVE DISORDER present in neurotic and psychotic disorders.	2.88	3	0
Age-Related Memory Disorders [description not available]	2.21	1	0
Memory Disorders Disturbances in registering an impression, in the retention of an acquired impression, or in the recall of an impression. Memory impairments are associated with DEMENTIA; CRANIOCEREBRAL TRAUMA; ENCEPHALITIS; ALCOHOLISM (see also ALCOHOL AMNESTIC DISORDER); SCHIZOPHRENIA; and other conditions.	2.21	1	0
Testicular Diseases Pathological processes of the TESTIS.	2.21	1	0
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	2.46	2	0
Skin Aging The process of aging due to changes in the structure and elasticity of the skin over time. It may be a part of physiological aging or it may be due to the effects of ultraviolet radiation, usually through exposure to sunlight.	8.64	1	1
Fish Diseases Diseases of freshwater, marine, hatchery or aquarium fish. This term includes diseases of both teleosts (true fish) and elasmobranchs (sharks, rays and skates).	2.08	1	0
Condition, Preneoplastic [description not available]	2.69	3	0
Precancerous Conditions Pathological conditions that tend eventually to become malignant.	2.69	3	0
Liver Dysfunction [description not available]	3.67	3	0
Liver Diseases Pathological processes of the LIVER.	3.67	3	0
Age-Related Osteoporosis [description not available]	2.1	1	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.	2.1	1	0
Injury, Myocardial Reperfusion [description not available]	2.52	2	0
Heart Disease, Ischemic [description not available]	2.74	3	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).	7.74	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.	2.1	1	0
Pneumonia, Viral Inflammation of the lung parenchyma that is caused by a viral infection.	2.1	1	0
Carcinoma, Non-Small Cell Lung [description not available]	2.1	1	0
Carcinoma, Non-Small-Cell Lung A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.	2.1	1	0
Bacterial Skin Diseases [description not available]	2.1	1	0
Skin Diseases, Bacterial Skin diseases caused by bacteria.	2.1	1	0
Parodontosis [description not available]	2.11	1	0
Periodontal Diseases Pathological processes involving the PERIODONTIUM including the gum (GINGIVA), the alveolar bone (ALVEOLAR PROCESS), the DENTAL CEMENTUM, and the PERIODONTAL LIGAMENT.	2.11	1	0
Burns Injuries to tissues caused by contact with heat, steam, chemicals (BURNS, CHEMICAL), electricity (BURNS, ELECTRIC), or the like.	2.11	1	0
Weight Gain Increase in BODY WEIGHT over existing weight.	2.77	3	0
Bone Loss, Osteoclastic [description not available]	2.13	1	0
Hyperlipemia [description not available]	2.49	2	0
Hyperlipidemias Conditions with excess LIPIDS in the blood.	2.49	2	0
Blood Clot [description not available]	2.8	3	0
Thrombosis Formation and development of a thrombus or blood clot in the blood vessel.	2.8	3	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)	2.13	1	0
Cancer of Mouth [description not available]	2.7	3	0
Cancer of Pharynx [description not available]	2.13	1	0
Mouth Neoplasms Tumors or cancer of the MOUTH.	2.7	3	0
Pharyngeal Neoplasms Tumors or cancer of the PHARYNX.	2.13	1	0
Acute Disease Disease having a short and relatively severe course.	2.13	1	0
Anxiety Feelings or emotions of dread, apprehension, and impending disaster but not disabling as with ANXIETY DISORDERS.	2.15	1	0
Angina at Rest [description not available]	2.05	1	0
Angina, Unstable Precordial pain at rest, which may precede a MYOCARDIAL INFARCTION.	2.05	1	0
Cancer of Cervix [description not available]	2.05	1	0
Uterine Cervical Neoplasms Tumors or cancer of the UTERINE CERVIX.	2.05	1	0
Itching [description not available]	2.05	1	0
Pruritus An intense itching sensation that produces the urge to rub or scratch the skin to obtain relief.	2.05	1	0
Pheochromocytoma, Extra-Adrenal [description not available]	2.05	1	0
Pheochromocytoma A usually benign, well-encapsulated, lobular, vascular tumor of chromaffin tissue of the ADRENAL MEDULLA or sympathetic paraganglia. The cardinal symptom, reflecting the increased secretion of EPINEPHRINE and NOREPINEPHRINE, is HYPERTENSION, which may be persistent or intermittent. During severe attacks, there may be HEADACHE; SWEATING, palpitation, apprehension, TREMOR; PALLOR or FLUSHING of the face, NAUSEA and VOMITING, pain in the CHEST and ABDOMEN, and paresthesias of the extremities. The incidence of malignancy is as low as 5% but the pathologic distinction between benign and malignant pheochromocytomas is not clear. (Dorland, 27th ed; DeVita Jr et al., Cancer: Principles & Practice of Oncology, 3d ed, p1298)	7.05	1	0
MPTP Neurotoxicity Syndrome [description not available]	2.05	1	0
Metastase [description not available]	2.06	1	0
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	2.06	1	0
Leucocythaemia [description not available]	2.43	2	0
Leukemia A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)	7.43	2	0
Adjuvant Arthritis [description not available]	2.36	2	0
Granulomas [description not available]	2.06	1	0
Granuloma A relatively small nodular inflammatory lesion containing grouped mononuclear phagocytes, caused by infectious and noninfectious agents.	2.06	1	0
Coronary Heart Disease [description not available]	2.4	2	0
Coronary Disease An imbalance between myocardial functional requirements and the capacity of the CORONARY VESSELS to supply sufficient blood flow. It is a form of MYOCARDIAL ISCHEMIA (insufficient blood supply to the heart muscle) caused by a decreased capacity of the coronary vessels.	2.4	2	0
Anemia A reduction in the number of circulating ERYTHROCYTES or in the quantity of HEMOGLOBIN.	2.99	1	0
Elevated Cholesterol [description not available]	2.07	1	0
Hypercholesterolemia A condition with abnormally high levels of CHOLESTEROL in the blood. It is defined as a cholesterol value exceeding the 95th percentile for the population.	2.07	1	0
Bleeding [description not available]	2.07	1	0
Hemorrhage Bleeding or escape of blood from a vessel.	2.07	1	0
Chronic Lung Injury [description not available]	2.07	1	0
Airway Hyper-Responsiveness [description not available]	2.08	1	0
Carbon Tetrachloride Poisoning Poisoning that results from ingestion, injection, inhalation, or skin absorption of CARBON TETRACHLORIDE.	2.03	1	0
Nerve Degeneration Loss of functional activity and trophic degeneration of nerve axons and their terminal arborizations following the destruction of their cells of origin or interruption of their continuity with these cells. The pathology is characteristic of neurodegenerative diseases. Often the process of nerve degeneration is studied in research on neuroanatomical localization and correlation of the neurophysiology of neural pathways.	2.72	3	0
Cancer of Stomach [description not available]	2.4	2	0
Stomach Neoplasms Tumors or cancer of the STOMACH.	2.4	2	0
Encephalopathy, Toxic [description not available]	2.04	1	0
Angor Pectoris [description not available]	2.36	2	0
Angina Pectoris The symptom of paroxysmal pain consequent to MYOCARDIAL ISCHEMIA usually of distinctive character, location and radiation. It is thought to be provoked by a transient stressful situation during which the oxygen requirements of the MYOCARDIUM exceed that supplied by the CORONARY CIRCULATION.	2.36	2	0
Bladder Cancer [description not available]	1.98	1	0
Carcinoma, Anaplastic [description not available]	1.98	1	0
Papilloma, Squamous Cell [description not available]	3.08	5	0
Urinary Bladder Neoplasms Tumors or cancer of the URINARY BLADDER.	1.98	1	0
Carcinoma A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.	1.98	1	0
Papilloma A circumscribed benign epithelial tumor projecting from the surrounding surface; more precisely, a benign epithelial neoplasm consisting of villous or arborescent outgrowths of fibrovascular stroma covered by neoplastic cells. (Stedman, 25th ed)	3.08	5	0
Cancer of Digestive System [description not available]	1.98	1	0
Digestive System Neoplasms Tumors or cancer of the DIGESTIVE SYSTEM.	1.98	1	0
Cancer of the Tongue [description not available]	1.98	1	0
Tongue Neoplasms Tumors or cancer of the TONGUE.	1.98	1	0
Adenoma, Basal Cell [description not available]	2.39	2	0
Adenoma A benign epithelial tumor with a glandular organization.	2.39	2	0
Experimental Neoplasms [description not available]	1.99	1	0
Bacterial Infections, Gram-Positive [description not available]	1.99	1	0
Gram-Positive Bacterial Infections Infections caused by bacteria that retain the crystal violet stain (positive) when treated by the gram-staining method.	1.99	1	0
Hyperplasia An increase in the number of cells in a tissue or organ without tumor formation. It differs from HYPERTROPHY, which is an increase in bulk without an increase in the number of cells.	2.39	2	0
Akinetic-Rigid Variant of Huntington Disease [description not available]	1.99	1	0
Huntington Disease A familial disorder inherited as an autosomal dominant trait and characterized by the onset of progressive CHOREA and DEMENTIA in the fourth or fifth decade of life. Common initial manifestations include paranoia; poor impulse control; DEPRESSION; HALLUCINATIONS; and DELUSIONS. Eventually intellectual impairment; loss of fine motor control; ATHETOSIS; and diffuse chorea involving axial and limb musculature develops, leading to a vegetative state within 10-15 years of disease onset. The juvenile variant has a more fulminant course including SEIZURES; ATAXIA; dementia; and chorea. (From Adams et al., Principles of Neurology, 6th ed, pp1060-4)	1.99	1	0
Experimental Mammary Neoplasms [description not available]	2	1	0
Anterior Circulation Transient Ischemic Attack [description not available]	2	1	0
Ischemic Attack, Transient Brief reversible episodes of focal, nonconvulsive ischemic dysfunction of the brain having a duration of less than 24 hours, and usually less than one hour, caused by transient thrombotic or embolic blood vessel occlusion or stenosis. Events may be classified by arterial distribution, temporal pattern, or etiology (e.g., embolic vs. thrombotic). (From Adams et al., Principles of Neurology, 6th ed, pp814-6)	2	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.	2.01	1	0
Injuries Used with anatomic headings, animals, and sports for wounds and injuries. Excludes cell damage, for which pathology is used.	6.29	9	0
Wounds and Injuries Damage inflicted on the body as the direct or indirect result of an external force, with or without disruption of structural continuity.	6.29	9	0
Leiomyosarcoma, Epithelioid [description not available]	1.98	1	0
Leiomyosarcoma A sarcoma containing large spindle cells of smooth muscle. Although it rarely occurs in soft tissue, it is common in the viscera. It is the most common soft tissue sarcoma of the gastrointestinal tract and uterus. The median age of patients is 60 years. (From Dorland, 27th ed; Holland et al., Cancer Medicine, 3d ed, p1865)	1.98	1	0
Chromosome Deletion Actual loss of portion of a chromosome.	1.97	1	0

protocatechuic acid

Description

Cross-References

Synonyms (87)

Research Excerpts

Overview

Effects

Actions

Treatment

Toxicity

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Dosage Studied

Roles (5)

Drug Classes (2)

Pathways (6)

Protein Targets (39)

Potency Measurements

Inhibition Measurements

Activation Measurements

Biological Processes (131)

Molecular Functions (38)

Ceullar Components (45)

Bioassays (236)

Research

Studies (937)

Market Indicators

Research Demand Index: 53.43

Study Types

Clinical Trials (1)

Trial Overview

protocatechuic acid

Description

Cross-References

Synonyms (87)

Research Excerpts

Overview

Effects

Actions

Treatment

Toxicity

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Dosage Studied

Roles (5)

Drug Classes (2)

Pathways (6)

Protein Targets (39)

Potency Measurements

Inhibition Measurements

Activation Measurements

Biological Processes (131)

Molecular Functions (38)

Ceullar Components (45)

Bioassays (236)

Research

Studies (937)

Market Indicators

Research Demand Index: 53.43

Study Types

Clinical Trials (1)

Trial Overview

Related Drugs (947)

Related Conditions (374)