4-hydroxyphenylethanol profile

4-Hydroxyphenylethanol, also known as tyrosol, is a natural phenolic compound found in olive oil, wine, and other plant sources. It exhibits antioxidant and anti-inflammatory properties, and has been studied for its potential benefits in cardiovascular health, neuroprotection, and anti-cancer activity. Tyrosol is synthesized via the decarboxylation of tyrosine by the enzyme tyrosine decarboxylase. It is also produced by the yeast Saccharomyces cerevisiae during the fermentation of grapes. Research on tyrosol focuses on its various biological activities and potential applications in pharmaceuticals, cosmetics, and food preservation.'

4-hydroxyphenylethanol: in chest gland secretion of galagos [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

2-(4-hydroxyphenyl)ethanol : A phenol substituted at position 4 by a 2-hydroxyethyl group. [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	10393
CHEMBL ID	53566
CHEBI ID	1879
SCHEMBL ID	43838
SCHEMBL ID	10620528
MeSH ID	M0058493

Synonym
tyrosol c
p-tyrosol
1ak4mu3snx ,
unii-1ak4mu3snx
4-hydroxybenzeneethanol
CHEBI:1879 ,
2-(4-hydroxyphenyl)ethanol
nsc59876
p-hydroxyphenethyl alcohol
nsc-59876
benzeneethanol, 4-hydroxy-
inchi=1/c8h10o2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,9-10h,5-6h
4-(2-hydroxyethyl)phenol
501-94-0
C06044
tyrosol
4-hydroxyphenylethanol
2-(4-hydroxyphenyl)ethanol, 98%
nsc 59876
einecs 207-930-8
4-hydroxyphenethyl alcohol
MLS001332423
MLS001332424
smr000857159
4-tyrosol
p-hydroxyphenylethanol
AC-2493
ethanol, 2-(4-hydroxyphenyl)-
947D0361-23C6-4863-8346-22AB05108AC5
AKOS000280287
CHEMBL53566 ,
BMSE000173
2-(p-hydroxyphenyl)ethanol
2-(4-hydroxyphenyl)ethyl alcohol
H0720
NCGC00246994-01
bdbm50339585
4-(2-hydroxy-ethyl)-phenol
4-hydroxyphenylethyl alcohol
HMS2230E12
S3773
p-hpea
FT-0608647
AM20060146
beta-(4-hydroxyphenyl)ethanol
4-hydroxy-benzeneethanol;4-hydroxyphenylethanol;beta-(4-hydroxyphenyl)ethanol
para-hydroxyphenylethanol
n-tyrosol
SCHEMBL43838
KS-5274
yrl ,
tyrosol (constituent of rhodiola rosea) [dsc]
metoprolol succinate impurity g [ep impurity]
hydroxyphenethyl alcohol, p-
tyrosol [mi]
metoprolol tartrate impurity g [ep impurity]
mfcd00002902
SY001653
SCHEMBL10620528
DTXSID8060111 ,
2-(4-hydroxyphenyl) ethanol
(4-hydroxyphenethyl) alcohol
2-(4-hydroxyphenyl)-ethanol
2-(4-hydroxyphenyl)-1-ethanol
4-hydroxyphenethylalcohol
2-(p-hydroxyphenyl) ethanol
4-hydroxybenzenethanol
4-(hydroxyethyl)phenol
4-hydroxyphenylmethylcarbinol
STR02735
CS-W019782
p-hydroxy-benzeneethanol
.beta.-(p-hydroxyphenyl)ethanol
ethanol, 2-(4-hydroxyphenyl)
.beta.-(4-hydroxyphenyl)ethanol
phenethyl alcohol, p-hydroxy-
p-hydroxyphenylethyl alcohol
p-thyrosol
metoprolol impurity 07
F0001-1309
2-(4-hydroxyphenyl)ethanol, analytical standard
beta-(p-hydroxyphenyl)ethanol
b-(4-hydroxyphenyl)ethanol
b-(p-hydroxyphenyl)ethanol
4-hydroxy-benzeneethanol
HY-N0474
tyrosol ,(s)
Q402607
A14486
EN300-116733
nsc 59876; p-hpea;4-hydroxyphenethyl alcohol
BCP34277
CCG-266147
tyrosol (constituent of rhodiola rosea)
metoprolol succinate impurity g (ep impurity)
dtxcid7040780
metoprolol tartrate impurity g (ep impurity)
Z1250886919

Excerpt	Reference	Relevance
" The protective effects of the tested extracts or isolated compounds were evaluated from their ability to decrease hydrogen peroxide-induced formation of single strand breaks in the nuclear DNA, while the toxic effects were estimated from the increase of DNA damage when the extracts or isolated compounds were incubated directly with the cells."	( DNA protecting and genotoxic effects of olive oil related components in cells exposed to hydrogen peroxide. Agalias, A; Aligiannis, N; Bazios, D; Doulias, PT; Galaris, D; Mitakou, S; Nousis, L, 2005)	0.33

Excerpt	Reference	Relevance
"The main pharmacokinetic parameters ofp-tyrosol upon intravenous injection have been experimentally studied in rats."	( [The main pharmacokinetic parameters of p-tyrosol upon intravenous injection in rats]. Cherkashina, IV; Chernysheva, GA; Krysin, AP; Plotnikov, MB; Smol'niakova, VI; Sorokina, IV; Tolstikova, TG, )	0.13
"The main pharmacokinetic parameters of p-tyrosol after single (in 3 doses) and repeated intravenous injection were studied in rats."	( [The main pharmacokinetic parameters of p-tyrosol upon intravenous injection in rats. II. Verification of the pharmacokinetics linearity and evaluation of the possible accumulation]. Cherkashina, IV; Chernysheva, GA; Krysin, AP; Plotnikov, MB; Smol'iakova, VI; Sorokina, IV; Tolstikova, TG, )	0.13
" Thus, the pharmacokinetic characteristics in rat and the gut microbial degradation of tyrosol acyl esters (TYr-Es) with fatty acids of C12:0, C18:0, and C18:2 were investigated for the first time."	( Evaluation of Absorption and Plasma Pharmacokinetics of Tyrosol Acyl Esters in Rats. Hu, Y; Liu, X; Qin, L; Shahidi, F; Wang, X; Xie, H; Yin, F; Zhang, J; Zhou, D, 2020)	0.56

Excerpt	Reference	Relevance
" One of the prerequisites to extrapolate these data to an in vivo situation is the knowledge of their bioavailability in humans."	( Capillary gas chromatography-mass spectrometry quantitative determination of hydroxytyrosol and tyrosol in human urine after olive oil intake. Covas, MI; de la Torre, R; Farré Albaladejo, M; Lamuela Raventós, RM; Menoyo Colomer, E; Miró-Casas, E; Rodriguez, JO, 2001)	0.31
" Oral bioavailability estimates of hydroxytyrosol when administered in an olive oil solution and when dosed as an aqueous solution were 99% and 75%, respectively."	( The in vivo fate of hydroxytyrosol and tyrosol, antioxidant phenolic constituents of olive oil, after intravenous and oral dosing of labeled compounds to rats. Freeman, MP; Hayball, PJ; Stretch, GL; Stupans, I; Tuck, KL, 2001)	0.31
" We have demonstrated the bioavailability of tyrosol in humans from virgin olive oil in its natural form."	( Bioavailability of tyrosol, an antioxidant phenolic compound present in wine and olive oil, in humans. Covas, MI; De La Torre, R; Farré-Albadalejo, M; Fitó, M; Gimeno, E; Marrugat, J; Miró-Casas, E, 2003)	0.32
" The method has been successfully applied to the pharmacokinetic study and the oral bioavailability was calculated."	( Simultaneous determination of salidroside and its aglycone metabolite p-tyrosol in rat plasma by liquid chromatography-tandem mass spectrometry. Fan, X; Guo, N; Hu, Z; Li, H; Wang, Y; Xu, T; Yu, T; Zhang, D; Zheng, J, 2012)	0.38
" Further studies are needed to determine the bioavailability of these compounds and their possible beneficial health effects when taken by moderate beer consumption."	( Beer and beer compounds: physiological effects on skin health. Becker, T; Chen, W; Qian, F; Ring, J, 2014)	0.4
" However, the bioavailability of the most important of these compounds, hydroxytyrosol (HT), and its transformation into derivatives within the organism after oral intake are still not completely understood, requiring further in vivo research."	( Gender differences in plasma and urine metabolites from Sprague-Dawley rats after oral administration of normal and high doses of hydroxytyrosol, hydroxytyrosol acetate, and DOPAC. Auñón, D; Domínguez-Perles, R; Ferreres, F; Gil-Izquierdo, A, 2017)	0.46
"Plasma and urine levels indicated that although the three compounds are efficiently absorbed in the gastrointestinal tract and show similar metabolism, the bioavailability is strongly dependent on the derivative considered, dosage, and gender."	( Gender differences in plasma and urine metabolites from Sprague-Dawley rats after oral administration of normal and high doses of hydroxytyrosol, hydroxytyrosol acetate, and DOPAC. Auñón, D; Domínguez-Perles, R; Ferreres, F; Gil-Izquierdo, A, 2017)	0.46
" In this regard, information regarding the bioavailability and metabolic disposition of hydroxytyrosol and tyrosol is of most importance to evaluate the impact they may have on human health."	( Metabolic disposition and biological significance of simple phenols of dietary origin: hydroxytyrosol and tyrosol. Boronat, A; de la Torre, R; Farré, M; Fitó, M; Khymenets, O; Kotronoulas, A; Olesti, E; Pastor, A; Pérez-Mañá, C; Pujadas, M; Rodríguez-Morató, J, 2016)	0.43
" These natural antioxidants molecules revealed several beneficial effects on human health, but a low bioavailability and accessibility to targeted site."	( Chemical characterization of liposomes containing nutraceutical compounds: Tyrosol, hydroxytyrosol and oleuropein. Bonechi, C; Consumi, M; Donati, A; Lamponi, S; Leone, G; Magnani, A; Pardini, A; Rossi, C; Rostom, H; Tamasi, G, 2019)	0.51
"Acrylamide and phenolic compounds on both fresh and cooked olives were monitored by HPLC/MS-MS and reversed-phase-HPLC methods along different procedures: elaboration process, high hydrostatic pressure (HHP), cooking treatment and bioavailability evaluation."	( Monitoring of acrylamide and phenolic compounds in table olive after high hydrostatic pressure and cooking treatments. Cabrera-Bañegil, M; Delgado-Adámez, J; Fernández, A; Lodolini, EM; Martín-Vertedor, D; Ramírez, R, 2019)	0.51
" This review summarizes recent findings regarding biological activities, metabolism and bioavailability of the major olive oil phenolic compounds-hydroxytyrosol, tyrosol, oleuropein, oleocanthal and oleacein-the most important being their antiatherogenic, cardioprotective, anticancer, neuroprotective and endocrine effects."	( Hydroxytyrosol, Tyrosol and Derivatives and Their Potential Effects on Human Health. Barbarić, M; Jakobušić Brala, C; Karković Marković, A; Torić, J, 2019)	0.51
" However, they have low bioavailability due to their low absorption and high metabolism in human liver and small intestine."	( De novo biosynthesis of tyrosol acetate and hydroxytyrosol acetate from glucose in engineered Escherichia coli. Fu, X; Guo, D; Li, X; Pan, H; Sun, Y, 2021)	0.62

Excerpt	Relevance	Reference
" For both compounds, the intravenously and orally administered oil-based dosings resulted in significantly greater elimination of the phenolics in urine within 24 h than the oral, aqueous dosing method."	( The in vivo fate of hydroxytyrosol and tyrosol, antioxidant phenolic constituents of olive oil, after intravenous and oral dosing of labeled compounds to rats. Freeman, MP; Hayball, PJ; Stretch, GL; Stupans, I; Tuck, KL, 2001)	0.31
" This method has the advantages of simple process and operation, less dosage of organic solvent, highly yield and reproducibility, suitable for the simultaneously preparation of tyrosol, crenulatin and salidroside."	( [Simultaneously preparation of grams of high purity tyrosol, crenulatin and salidroside from Rhodiola crenulata]. Li, SP; Luo, X; Wang, XJ; Wang, ZZ; Xiao, W; Zhang, Q; Zhao, YW, 2015)	0.42
" With extraction rate of salidroside, tyrosol, crenulatin and gallic acid as indexes, orthogonal test was used to evaluate effect of 4 factors on extracting technology, including concentration of solvent, the dosage of solvent, duration of extraction, and frequency of extraction."	( [Optimization of extraction technology for salidroside, tyrosol, crenulatin and gallic acid in Rhodiolae Crenulatae Radix et Rhizoma with orthogonal test]. Huang, WZ; Luo, X; Wang, XJ; Wang, ZZ; Xiao, W; Zhao, YW, 2015)	0.42
" The effects of substrate concentration, temperature, pH, time, and enzyme dosage on the concentration of TF produced are studied using the design of experiments methodology."	( Screening of Commercial Enzymes for Transfructosylation of Tyrosol: Effect of Process Conditions and Reaction Network. Antošová, M; Hollá, V; Karkeszová, K; Mastihuba, V; Polakovič, M, 2019)	0.51
" This work has studied the extraction of phenolic compounds from a type of OMWW, olive vegetation water, which presents these compounds in a more diluted dosage than in other studied to date, to revalue this waste stream."	( Sustainable recovery of phenolic antioxidants from real olive vegetation water with natural hydrophobic eutectic solvents and terpenoids. Álvarez-Torrellas, S; García, J; Larriba, M; Martín-Gutiérrez, D; Navarro, P; Rodríguez-Llorente, D; Suárez-Rodríguez, P, 2023)	0.91

Role	Description
anti-arrhythmia drug	A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.
antioxidant	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
cardiovascular drug	A drug that affects the rate or intensity of cardiac contraction, blood vessel diameter or blood volume.
protective agent	Synthetic or natural substance which is given to prevent a disease or disorder or are used in the process of treating a disease or injury due to a poisonous agent.
fungal metabolite	Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
geroprotector	Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
plant metabolite	Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[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
phenols	Organic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring.
[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
salidroside biosynthesis	2	15
L-tyrosine degradation III	9	13
tyrosine degradation III	12	12

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
GLS protein	Homo sapiens (human)	Potency	10.0000	0.3548	7.9355	39.8107	AID624170
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Carbonic anhydrase 1	Homo sapiens (human)	Ki	430.0000	0.0000	1.3726	10.0000	AID588186
Carbonic anhydrase 2	Homo sapiens (human)	Ki	8.7000	0.0000	0.7236	9.9200	AID588187
Hepatocyte growth factor receptor	Homo sapiens (human)	IC50 (µMol)	20.0000	0.0004	0.3722	10.0000	AID1311093
Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	IC50 (µMol)	6.6800	0.0002	2.4585	9.9600	AID1884016
Carbonic anhydrase	Mycobacterium tuberculosis H37Rv	Ki	12.1000	0.0120	2.7238	9.1200	AID588182
Beta-carbonic anhydrase 1	Mycobacterium tuberculosis H37Rv	Ki	0.8500	0.0048	3.3841	9.8400	AID588183
Carbonic anhydrase	Cryptococcus neoformans var. grubii	Ki	1.0800	0.0100	0.7364	8.3470	AID588185
Carbonic anhydrase	Candida albicans SC5314	Ki	1.1000	0.0105	1.4444	8.3470	AID588184
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Carbonic anhydrase 1	Homo sapiens (human)	Kinact	430.0000	0.0100	0.9387	8.6000	AID456398
Carbonic anhydrase 2	Homo sapiens (human)	Kinact	8.7000	0.0030	0.7946	10.0000	AID456397
Carbonic anhydrase 5A, mitochondrial	Homo sapiens (human)	Kinact	0.1010	0.0200	0.8580	9.4000	AID456399
Carbonic anhydrase 5B, mitochondrial	Homo sapiens (human)	Kinact	0.1050	0.0090	0.9231	9.0400	AID456400
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
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)
endothelial cell morphogenesis	Hepatocyte growth factor receptor	Homo sapiens (human)
signal transduction	Hepatocyte growth factor receptor	Homo sapiens (human)
cell surface receptor signaling pathway	Hepatocyte growth factor receptor	Homo sapiens (human)
negative regulation of autophagy	Hepatocyte growth factor receptor	Homo sapiens (human)
positive regulation of microtubule polymerization	Hepatocyte growth factor receptor	Homo sapiens (human)
negative regulation of Rho protein signal transduction	Hepatocyte growth factor receptor	Homo sapiens (human)
positive regulation of transcription by RNA polymerase II	Hepatocyte growth factor receptor	Homo sapiens (human)
hepatocyte growth factor receptor signaling pathway	Hepatocyte growth factor receptor	Homo sapiens (human)
branching morphogenesis of an epithelial tube	Hepatocyte growth factor receptor	Homo sapiens (human)
positive chemotaxis	Hepatocyte growth factor receptor	Homo sapiens (human)
negative regulation of stress fiber assembly	Hepatocyte growth factor receptor	Homo sapiens (human)
excitatory postsynaptic potential	Hepatocyte growth factor receptor	Homo sapiens (human)
establishment of skin barrier	Hepatocyte growth factor receptor	Homo sapiens (human)
negative regulation of thrombin-activated receptor signaling pathway	Hepatocyte growth factor receptor	Homo sapiens (human)
semaphorin-plexin signaling pathway	Hepatocyte growth factor receptor	Homo sapiens (human)
negative regulation of hydrogen peroxide-mediated programmed cell death	Hepatocyte growth factor receptor	Homo sapiens (human)
negative regulation of guanyl-nucleotide exchange factor activity	Hepatocyte growth factor receptor	Homo sapiens (human)
positive regulation of endothelial cell chemotaxis	Hepatocyte growth factor receptor	Homo sapiens (human)
liver development	Hepatocyte growth factor receptor	Homo sapiens (human)
cell surface receptor protein tyrosine kinase signaling pathway	Hepatocyte growth factor receptor	Homo sapiens (human)
phagocytosis	Hepatocyte growth factor receptor	Homo sapiens (human)
multicellular organism development	Hepatocyte growth factor receptor	Homo sapiens (human)
neuron differentiation	Hepatocyte growth factor receptor	Homo sapiens (human)
positive regulation of kinase activity	Hepatocyte growth factor receptor	Homo sapiens (human)
cell migration	Hepatocyte growth factor receptor	Homo sapiens (human)
pancreas development	Hepatocyte growth factor receptor	Homo sapiens (human)
nervous system development	Hepatocyte growth factor receptor	Homo sapiens (human)
one-carbon metabolic process	Carbonic anhydrase 5A, mitochondrial	Homo sapiens (human)
response to bacterium	Carbonic anhydrase 5B, mitochondrial	Homo sapiens (human)
one-carbon metabolic process	Carbonic anhydrase 5B, mitochondrial	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
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)
protein tyrosine kinase activity	Hepatocyte growth factor receptor	Homo sapiens (human)
protein binding	Hepatocyte growth factor receptor	Homo sapiens (human)
ATP binding	Hepatocyte growth factor receptor	Homo sapiens (human)
semaphorin receptor activity	Hepatocyte growth factor receptor	Homo sapiens (human)
protein phosphatase binding	Hepatocyte growth factor receptor	Homo sapiens (human)
identical protein binding	Hepatocyte growth factor receptor	Homo sapiens (human)
molecular function activator activity	Hepatocyte growth factor receptor	Homo sapiens (human)
hepatocyte growth factor receptor activity	Hepatocyte growth factor receptor	Homo sapiens (human)
3'-5'-RNA exonuclease activity	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2
RNA-dependent RNA polymerase activity	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2
cysteine-type endopeptidase activity	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2
mRNA 5'-cap (guanine-N7-)-methyltransferase activity	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2
mRNA (nucleoside-2'-O-)-methyltransferase activity	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2
mRNA guanylyltransferase activity	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2
RNA endonuclease activity, producing 3'-phosphomonoesters	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2
ISG15-specific peptidase activity	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2
5'-3' RNA helicase activity	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2
protein guanylyltransferase activity	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2
carbonate dehydratase activity	Carbonic anhydrase 5A, mitochondrial	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 5A, mitochondrial	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 5B, mitochondrial	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 5B, mitochondrial	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
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)
extracellular region	Hepatocyte growth factor receptor	Homo sapiens (human)
plasma membrane	Hepatocyte growth factor receptor	Homo sapiens (human)
basal plasma membrane	Hepatocyte growth factor receptor	Homo sapiens (human)
cell surface	Hepatocyte growth factor receptor	Homo sapiens (human)
membrane	Hepatocyte growth factor receptor	Homo sapiens (human)
postsynapse	Hepatocyte growth factor receptor	Homo sapiens (human)
basal plasma membrane	Hepatocyte growth factor receptor	Homo sapiens (human)
plasma membrane	Hepatocyte growth factor receptor	Homo sapiens (human)
receptor complex	Hepatocyte growth factor receptor	Homo sapiens (human)
double membrane vesicle viral factory outer membrane	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2
mitochondrial matrix	Carbonic anhydrase 5A, mitochondrial	Homo sapiens (human)
mitochondrion	Carbonic anhydrase 5A, mitochondrial	Homo sapiens (human)
cytoplasm	Carbonic anhydrase 5A, mitochondrial	Homo sapiens (human)
mitochondrion	Carbonic anhydrase 5A, mitochondrial	Homo sapiens (human)
mitochondrion	Carbonic anhydrase 5B, mitochondrial	Homo sapiens (human)
mitochondrial matrix	Carbonic anhydrase 5B, mitochondrial	Homo sapiens (human)
mitochondrion	Carbonic anhydrase 5B, mitochondrial	Homo sapiens (human)
cytoplasm	Carbonic anhydrase 5B, mitochondrial	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Assay ID	Title	Year	Journal	Article
AID651635	Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
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.
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.
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.
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.
AID1745845	Primary qHTS for Inhibitors of ATXN expression
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.
AID1317208	Cytotoxicity against human MRC5 cells assessed as inhibition of cell proliferation measured after 72 hrs by MTT assay	2016	European journal of medicinal chemistry, Aug-25, Volume: 119	Tyrosol and hydroxytyrosol derivatives as antitrypanosomal and antileishmanial agents.
AID361510	Cytotoxicity against human Hep3B cells	2008	Journal of natural products, Aug, Volume: 71, Issue:8	Characterization of polyketide metabolites from foliar endophytes of Picea glauca.
AID1754866	Antiproliferative activity against human PC-3 cells assessed as reduction in cell growth at 100 uM incubated for 72 hrs by trypan blue assay relative to control	2021	Bioorganic & medicinal chemistry, 07-15, Volume: 42	Solid-phase synthesis of curcumin mimics and their anticancer activity against human pancreatic, prostate, and colorectal cancer cell lines.
AID361511	Toxicity against Choristoneura fumiferana assessed as reduction in body weight by diet incorporation assay	2008	Journal of natural products, Aug, Volume: 71, Issue:8	Characterization of polyketide metabolites from foliar endophytes of Picea glauca.
AID1232402	Activity at mushroom tyrosinase assessed as decrease in absorbance using L-dopa as substrate by oxygen consumption assay	2015	Bioorganic & medicinal chemistry, Jul-01, Volume: 23, Issue:13	Identification of p-hydroxybenzyl alcohol, tyrosol, phloretin and its derivate phloridzin as tyrosinase substrates.
AID1706732	Neuroprotective activity against CoCl2-induced cytotoxicity in rat PC12 cells assessed as increase in cell viability at 1 uM pretreated with CoCl2 for 8 hrs followed by incubation with drug and measured after 24 hrs by MTT assay	2021	European journal of medicinal chemistry, Jan-01, Volume: 209	Synthesis and identification of a novel derivative of salidroside as a selective, competitive inhibitor of monoamine oxidase B with enhanced neuroprotective properties.
AID361512	Toxicity against Saccharomyces cerevisiae by disc diffusion method	2008	Journal of natural products, Aug, Volume: 71, Issue:8	Characterization of polyketide metabolites from foliar endophytes of Picea glauca.
AID740159	Cytotoxicity against human MCF10A cells at IC50 in wound healing assay after 24 hrs by MTT assay	2013	Bioorganic & medicinal chemistry, Apr-01, Volume: 21, Issue:7	Olive secoiridoids and semisynthetic bioisostere analogues for the control of metastatic breast cancer.
AID1232393	Inhibition of diphenolase activity of mushroom tyrosinase using L-dopa as substrate at 0.5 mM by spectrophotometric assay	2015	Bioorganic & medicinal chemistry, Jul-01, Volume: 23, Issue:13	Identification of p-hydroxybenzyl alcohol, tyrosol, phloretin and its derivate phloridzin as tyrosinase substrates.
AID1090647	Antifungal activity against Verticillium dahliae assessed as inhibition of mycelial radial growth measured after 350 hr	2007	Journal of agricultural and food chemistry, May-02, Volume: 55, Issue:9	Dysfunctionality of the xylem in Olea europaea L. Plants associated with the infection process by Verticillium dahliae Kleb. Role of phenolic compounds in plant defense mechanism.
AID1884016	Inhibition of SARS-CoV-2 papain-like protease using ISG15-Rh as substrate	2022	Journal of medicinal chemistry, 06-09, Volume: 65, Issue:11	Progress and Challenges in Targeting the SARS-CoV-2 Papain-like Protease.
AID588190	Selectivity ratio of Ki for human recombinant alpha-carbonic anhydrase 1 to Ki for Mycobacterium tuberculosis recombinant Rv3273 beta-carbonic anhydrase	2011	Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6	Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID456404	Selectivity ratio of Kinact for human recombinant carbonic anhydrase 2 to Kinact for human recombinant carbonic anhydrase 5B	2010	Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1	Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.
AID1317212	Antileishmanial activity against Leishmania donovani MHOM/ET/67/HU3 axenic amastigotes at 20 uM after 72 hrs by resazurin-based assay relative to control	2016	European journal of medicinal chemistry, Aug-25, Volume: 119	Tyrosol and hydroxytyrosol derivatives as antitrypanosomal and antileishmanial agents.
AID588187	Inhibition of human recombinant alpha-carbonic anhydrase 2 after 15 mins by stopped flow CO2 hydration assay	2011	Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6	Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID1694887	Induction of TrkB activation in human SH-SY5Y cells assessed as increase in phosphorylated TrkB level at 10 uM after 4 hrs by Western blot analysis	2020	RSC medicinal chemistry, Jan-01, Volume: 11, Issue:1	Conversion of amino acids to aryl/heteroaryl ethanol metabolites using human CYP2D6-expressing live baker's yeast.
AID456401	Selectivity ratio of Kinact for human recombinant carbonic anhydrase 1 to Kinact for human recombinant carbonic anhydrase 5A	2010	Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1	Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.
AID1694888	Neuroprotective activity against corticosterone-induced neurotoxicity in mouse N2a cells assessed as increase in cell viability at 10 uM preincubated for 24 hrs followed by corticosterone addition and measured after 24 hrs	2020	RSC medicinal chemistry, Jan-01, Volume: 11, Issue:1	Conversion of amino acids to aryl/heteroaryl ethanol metabolites using human CYP2D6-expressing live baker's yeast.
AID456402	Selectivity ratio of Kinact for human recombinant carbonic anhydrase 2 to Kinact for human recombinant carbonic anhydrase 5A	2010	Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1	Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.
AID740158	Cytotoxicity against human MCF10A cells at IC50 in MDA-MB-231 MTT assay after 24 hrs by MTT assay	2013	Bioorganic & medicinal chemistry, Apr-01, Volume: 21, Issue:7	Olive secoiridoids and semisynthetic bioisostere analogues for the control of metastatic breast cancer.
AID456399	Inhibition of human recombinant carbonic anhydrase 5A by stopped flow CO2 hydration method	2010	Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1	Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.
AID588194	Selectivity ratio of Ki for human recombinant alpha-carbonic anhydrase 2 to Ki for Mycobacterium tuberculosis recombinant Rv3273 beta-carbonic anhydrase	2011	Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6	Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID588192	Selectivity ratio of Ki for human recombinant alpha-carbonic anhydrase 1 to Ki for Candida albicans recombinant Nce103 beta-carbonic anhydrase	2011	Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6	Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID456397	Inhibition of human recombinant carbonic anhydrase 2 by stopped flow CO2 hydration method	2010	Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1	Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.
AID588186	Inhibition of human recombinant alpha-carbonic anhydrase 1 after 15 mins by stopped flow CO2 hydration assay	2011	Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6	Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID456400	Inhibition of human recombinant carbonic anhydrase 5B by stopped flow CO2 hydration method	2010	Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1	Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.
AID588184	Inhibition of Candida albicans recombinant Nce103 beta-carbonic anhydrase after 15 mins by stopped flow CO2 hydration assay	2011	Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6	Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID456398	Inhibition of human recombinant carbonic anhydrase 1 by stopped flow CO2 hydration method	2010	Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1	Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.
AID470188	Antioxidant activity assessed as oxygen radical scavenging activity by ORAC assay	2009	Journal of natural products, Nov, Volume: 72, Issue:11	Indole derivatives from a marine sponge-derived yeast as DPPH radical scavengers.
AID588183	Inhibition of Mycobacterium tuberculosis recombinant Rv1284 beta-carbonic anhydrase after 15 mins by stopped flow CO2 hydration assay	2011	Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6	Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID588196	Selectivity ratio of Ki for human recombinant alpha-carbonic anhydrase 2 to Ki for Candida albicans recombinant Nce103 beta-carbonic anhydrase	2011	Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6	Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID1754870	Antiproliferative activity against human PANC-1 cells assessed as cell death at 100 uM incubated for 72 hrs by trypan blue assay relative to control	2021	Bioorganic & medicinal chemistry, 07-15, Volume: 42	Solid-phase synthesis of curcumin mimics and their anticancer activity against human pancreatic, prostate, and colorectal cancer cell lines.
AID1232403	Activity at mushroom tyrosinase assessed as decrease in absorbance using DOMA as substrate by oxygen consumption assay	2015	Bioorganic & medicinal chemistry, Jul-01, Volume: 23, Issue:13	Identification of p-hydroxybenzyl alcohol, tyrosol, phloretin and its derivate phloridzin as tyrosinase substrates.
AID1317214	Selectivity index, ratio of IC50 for human MRC5 cells to IC50 for intracellular amastigotes of Leishmania donovani MHOM/ET/67/HU3 infected in human THP1 cells	2016	European journal of medicinal chemistry, Aug-25, Volume: 119	Tyrosol and hydroxytyrosol derivatives as antitrypanosomal and antileishmanial agents.
AID588193	Selectivity ratio of Ki for human recombinant alpha-carbonic anhydrase 1 to Ki for Cryptococcus neoformans recombinant Can2 beta-carbonic anhydrase	2011	Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6	Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID588185	Inhibition of Cryptococcus neoformans recombinant Can2 beta-carbonic anhydrase after 15 mins by stopped flow CO2 hydration assay	2011	Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6	Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID1694894	Induction of TrkB activation in human SH-SY5Y cells assessed as increase in ERK1/2 phosphorylation at 10 uM after 4 hrs by Western blot analysis	2020	RSC medicinal chemistry, Jan-01, Volume: 11, Issue:1	Conversion of amino acids to aryl/heteroaryl ethanol metabolites using human CYP2D6-expressing live baker's yeast.
AID1232404	Activity at mushroom tyrosinase by spectrophotometric assay in presence of hydrogen peroxide	2015	Bioorganic & medicinal chemistry, Jul-01, Volume: 23, Issue:13	Identification of p-hydroxybenzyl alcohol, tyrosol, phloretin and its derivate phloridzin as tyrosinase substrates.
AID1311098	Antimigratory activity against human MDA-MB-231 cells expressing c-MET assessed as inhibition of HGF-induced cell migration incubated for 24 hrs by Giemsa staining based wound healing assay	2016	European journal of medicinal chemistry, 08-08, Volume: 118	Novel c-Met inhibitory olive secoiridoid semisynthetic analogs for the control of invasive breast cancer.
AID1232395	Inhibition of diphenolase activity of mushroom tyrosinase using L-dopa as substrate at 1.5 mM by spectrophotometric assay	2015	Bioorganic & medicinal chemistry, Jul-01, Volume: 23, Issue:13	Identification of p-hydroxybenzyl alcohol, tyrosol, phloretin and its derivate phloridzin as tyrosinase substrates.
AID740160	Cytotoxicity against human MDA-MB-231 cells after 24 hrs by MTT assay	2013	Bioorganic & medicinal chemistry, Apr-01, Volume: 21, Issue:7	Olive secoiridoids and semisynthetic bioisostere analogues for the control of metastatic breast cancer.
AID1232394	Inhibition of diphenolase activity of mushroom tyrosinase using L-dopa as substrate at 1 mM by spectrophotometric assay	2015	Bioorganic & medicinal chemistry, Jul-01, Volume: 23, Issue:13	Identification of p-hydroxybenzyl alcohol, tyrosol, phloretin and its derivate phloridzin as tyrosinase substrates.
AID1694893	Induction of TrkB activation in human SH-SY5Y cells assessed as increase in Akt phosphorylation at 10 uM after 4 hrs by Western blot analysis	2020	RSC medicinal chemistry, Jan-01, Volume: 11, Issue:1	Conversion of amino acids to aryl/heteroaryl ethanol metabolites using human CYP2D6-expressing live baker's yeast.
AID1317207	Antitrypanosomal activity against Trypanosoma brucei rhodesiense	2016	European journal of medicinal chemistry, Aug-25, Volume: 119	Tyrosol and hydroxytyrosol derivatives as antitrypanosomal and antileishmanial agents.
AID1694889	Neuroprotective activity against corticosterone-induced neurotoxicity in human SH-SY5Y cells assessed as induction of BDNF neurotropic response at 10 uM preincubated for 2 hrs followed by corticosterone addition and measured after 4 hrs by ELISA	2020	RSC medicinal chemistry, Jan-01, Volume: 11, Issue:1	Conversion of amino acids to aryl/heteroaryl ethanol metabolites using human CYP2D6-expressing live baker's yeast.
AID1311093	Inhibition of recombinant human N-terminal His-tagged cytoplasmic c-MET kinase domain (956 to 1390 residues) phosphorylation expressed in baculovirus expression system using Tyr peptide-6 substrate incubated for 1 hr in presence of ATP by Z-Lyte assay	2016	European journal of medicinal chemistry, 08-08, Volume: 118	Novel c-Met inhibitory olive secoiridoid semisynthetic analogs for the control of invasive breast cancer.
AID1754867	Antiproliferative activity against human SW480 cells assessed as reduction in cell growth at 100 uM incubated for 72 hrs by trypan blue assay relative to control	2021	Bioorganic & medicinal chemistry, 07-15, Volume: 42	Solid-phase synthesis of curcumin mimics and their anticancer activity against human pancreatic, prostate, and colorectal cancer cell lines.
AID740168	Antimigratory activity against human MDA-MB-231 cells after 24 hrs by wound healing assay	2013	Bioorganic & medicinal chemistry, Apr-01, Volume: 21, Issue:7	Olive secoiridoids and semisynthetic bioisostere analogues for the control of metastatic breast cancer.
AID588188	Inhibition of Mycobacterium tuberculosis recombinant Rv1284 beta-carbonic anhydrase after 15 mins by stopped flow CO2 hydration assay relative to phenol	2011	Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6	Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID588195	Selectivity ratio of Ki for human recombinant alpha-carbonic anhydrase 2 to Ki for Mycobacterium tuberculosis recombinant Rv1284 beta-carbonic anhydrase	2011	Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6	Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID1754868	Antiproliferative activity against human PC-3 cells assessed as cell death at 100 uM incubated for 72 hrs by trypan blue assay (Rvb = 3%)	2021	Bioorganic & medicinal chemistry, 07-15, Volume: 42	Solid-phase synthesis of curcumin mimics and their anticancer activity against human pancreatic, prostate, and colorectal cancer cell lines.
AID1311094	Antiproliferative activity against human MDA-MB-231 cells expressing c-MET assessed as inhibition of HGF-induced cell growth incubated for 72 hrs by MTT assay	2016	European journal of medicinal chemistry, 08-08, Volume: 118	Novel c-Met inhibitory olive secoiridoid semisynthetic analogs for the control of invasive breast cancer.
AID470187	Antioxidant activity assessed as DPPH radical scavenging activity at 300 uM after 48 hrs by spectrophotometry	2009	Journal of natural products, Nov, Volume: 72, Issue:11	Indole derivatives from a marine sponge-derived yeast as DPPH radical scavengers.
AID588197	Selectivity ratio of Ki for human recombinant alpha-carbonic anhydrase 2 to Ki for Cryptococcus neoformans recombinant Can2 beta-carbonic anhydrase	2011	Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6	Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID588191	Selectivity ratio of Ki for human recombinant alpha-carbonic anhydrase 1 to Ki for Mycobacterium tuberculosis recombinant Rv1284 beta-carbonic anhydrase	2011	Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6	Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID1232401	Activity at mushroom tyrosinase assessed as decrease in absorbance using L-tyrosine as substrate by oxygen consumption assay	2015	Bioorganic & medicinal chemistry, Jul-01, Volume: 23, Issue:13	Identification of p-hydroxybenzyl alcohol, tyrosol, phloretin and its derivate phloridzin as tyrosinase substrates.
AID1317213	Antileishmanial activity against Leishmania donovani MHOM/ET/67/HU3 intracellular amastigotes infected in human THP1 cells after 72 hrs by luciferase coupled luminescence assay	2016	European journal of medicinal chemistry, Aug-25, Volume: 119	Tyrosol and hydroxytyrosol derivatives as antitrypanosomal and antileishmanial agents.
AID1073064	Inhibition of human recombinant 5-lipoxygenase expressed in Escherichia coli Bl21 (DE3) using arachidonic acid as substrate preincubated at 10 uM for 10 mins before substrate addition measured after 10 mins by HPLC analysis	2014	Journal of natural products, Mar-28, Volume: 77, Issue:3	One-step semisynthesis of oleacein and the determination as a 5-lipoxygenase inhibitor.
AID1317210	Selectivity index, ratio of IC50 for human MRC5 cells to IC50 for bloodstream form of Trypanosoma brucei brucei S16	2016	European journal of medicinal chemistry, Aug-25, Volume: 119	Tyrosol and hydroxytyrosol derivatives as antitrypanosomal and antileishmanial agents.
AID740155	Inhibition of c-MET phosphorylation (unknown origin) at 25 uM after 1 hr by Z'-LYTE kinase assay	2013	Bioorganic & medicinal chemistry, Apr-01, Volume: 21, Issue:7	Olive secoiridoids and semisynthetic bioisostere analogues for the control of metastatic breast cancer.
AID740166	Antimigratory activity against human MDA-MB-231 cells at 50 uM after 24 hrs by wound healing assay	2013	Bioorganic & medicinal chemistry, Apr-01, Volume: 21, Issue:7	Olive secoiridoids and semisynthetic bioisostere analogues for the control of metastatic breast cancer.
AID588182	Inhibition of Mycobacterium tuberculosis recombinant Rv3273 beta-carbonic anhydrase after 15 mins by stopped flow CO2 hydration assay	2011	Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6	Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID1317209	Antitrypanosomal activity against bloodstream form of Trypanosoma brucei brucei S16 assessed as inhibition of proliferation measured after 72 hrs by alamarBlue assay	2016	European journal of medicinal chemistry, Aug-25, Volume: 119	Tyrosol and hydroxytyrosol derivatives as antitrypanosomal and antileishmanial agents.
AID1090673	Inhibition of ATP sythesis in freshly lysed Spinacia oleracea (spinach) chloroplasts	2007	Journal of agricultural and food chemistry, May-16, Volume: 55, Issue:10	Inhibition of photophosphorylation and electron transport chain in thylakoids by lasiodiplodin, a natural product from Botryosphaeria rhodina.
AID1754865	Antiproliferative activity against human PANC-1 cells assessed as reduction in cell growth at 100 uM incubated for 72 hrs by trypan blue assay relative to control	2021	Bioorganic & medicinal chemistry, 07-15, Volume: 42	Solid-phase synthesis of curcumin mimics and their anticancer activity against human pancreatic, prostate, and colorectal cancer cell lines.
AID456403	Selectivity ratio of Kinact for human recombinant carbonic anhydrase 1 to Kinact for human recombinant carbonic anhydrase 5B	2010	Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1	Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.
AID1311095	Antiproliferative activity against human MDA-MB-468 cells expressing c-MET assessed as inhibition of HGF-induced cell growth incubated for 72 hrs by MTT assay	2016	European journal of medicinal chemistry, 08-08, Volume: 118	Novel c-Met inhibitory olive secoiridoid semisynthetic analogs for the control of invasive breast cancer.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	7 (1.55)	18.7374
1990's	14 (3.10)	18.2507
2000's	112 (24.83)	29.6817
2010's	226 (50.11)	24.3611
2020's	92 (20.40)	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	12 (2.56%)	5.53%
Reviews	17 (3.63%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	439 (93.80%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (2)

Trial Overview

Trial	Enrollment	Study Type	Start Date	Status
Foods Such as Virgin Olive Oil Rich in Phenolic Compounds, and Prebiotic Supplementation: Dietary Strategy to Tackle Sarcopenia in Early Elderly Subjects (FOOP-Sarc) [NCT05485402]	135 participants (Anticipated)	Interventional	2022-09-01	Recruiting
A Single-center, Crossover, Randomized and Controlled Nutritional Intervention Clinical Trial. A Nutritional Intervention Study [NCT02783989]	33 participants (Actual)	Interventional	2016-01-20	Completed
[information is prepared from clinicaltrials.gov, extracted Sep-2024]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
protocatechuic acid protocatechuic acid: RN given refers to parent cpd; structure. 3,4-dihydroxybenzoic acid : A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4.	2.4	2	0	catechols; dihydroxybenzoic acid	antineoplastic agent; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor; human xenobiotic metabolite; plant metabolite
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.	2.11	1	0	benzyl alcohols; phenols	plant metabolite
4-hydroxybenzaldehyde [no description available]	3.65	2	0	hydroxybenzaldehyde	EC 1.14.17.1 (dopamine beta-monooxygenase) inhibitor; mouse metabolite; plant metabolite
4-hydroxyphenylacetic acid 4-hydroxyphenylacetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group.	3.41	7	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.	2.72	3	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.	2.11	1	0	ethanediol; glycol	metabolite; mouse metabolite; solvent; toxin
acetic acid Acetic Acid: Product of the oxidation of ethanol and of the destructive distillation of wood. It is used locally, occasionally internally, as a counterirritant and also as a reagent. (Stedman, 26th ed). acetic acid : A simple monocarboxylic acid containing two carbons.	2.52	2	0	monocarboxylic acid	antimicrobial food preservative; Daphnia magna metabolite; food acidity regulator; protic solvent
acetaldehyde Acetaldehyde: A colorless, flammable liquid used in the manufacture of acetic acid, perfumes, and flavors. It is also an intermediate in the metabolism of alcohol. It has a general narcotic action and also causes irritation of mucous membranes. Large doses may cause death from respiratory paralysis.. acetaldehyde : The aldehyde formed from acetic acid by reduction of the carboxy group. It is the most abundant carcinogen in tobacco smoke.. aldehyde : A compound RC(=O)H, in which a carbonyl group is bonded to one hydrogen atom and to one R group.. acetyl group : A group, formally derived from acetic acid by dehydroxylation, which is fundamental to the biochemistry of all forms of life. When bound to coenzyme A, it is central to the metabolism of carbohydrates and fats.	2.17	1	0	aldehyde	carcinogenic agent; EC 3.5.1.4 (amidase) inhibitor; electron acceptor; Escherichia coli metabolite; human metabolite; mouse metabolite; mutagen; oxidising agent; Saccharomyces cerevisiae metabolite; teratogenic agent
adenine [no description available]	1.98	1	0	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae 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.	2.02	1	0	benzyl alcohols	antioxidant; fragrance; metabolite; 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.	2.6	1	0	fatty acid 4:0; straight-chain saturated fatty acid	human urinary metabolite; Mycoplasma genitalium metabolite
formic acid formic acid: RN given refers to parent cpd. formic acid : The simplest carboxylic acid, containing a single carbon. Occurs naturally in various sources including the venom of bee and ant stings, and is a useful organic synthetic reagent. Principally used as a preservative and antibacterial agent in livestock feed. Induces severe metabolic acidosis and ocular injury in human subjects.	2.21	1	0	monocarboxylic acid	antibacterial agent; astringent; metabolite; protic solvent; solvent
catechol [no description available]	2.49	2	0	catechols	allelochemical; genotoxin; plant metabolite
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.	2.25	1	0	tricarboxylic acid	antimicrobial agent; chelator; food acidity regulator; fundamental 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).	2.15	1	0	monohydroxybenzoic acid	algal metabolite; antifungal agent; antiinfective agent; EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor; keratolytic drug; plant hormone; plant metabolite
gallic acid gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.	3.49	7	0	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
dihydrolipoic acid dihydrolipoic acid: RN given refers to parent cpd without isomeric designation. dihydrolipoic acid : A thio-fatty acid that is reduced form of lipoic acid. A potent antioxidant shown to directly destroy superoxide, hydroperoxy and hydroxyl radicals; also has neuroprotective and anti-tumour effects.. dihydrolipoate : The conjugate base of dihydrolipoic acid.	2.08	1	0	thio-fatty acid	antioxidant; human metabolite; neuroprotective agent
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.	3.14	5	0	catechols; dihydroxyphenylacetic acid	human metabolite
lactic acid Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.	2.25	1	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.	2.04	1	0	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
formaldehyde paraform: polymerized formaldehyde; RN given refers to parent cpd; used in root canal therapy	2.06	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
glycerol Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.	2.06	1	0	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
histamine [no description available]	2.13	1	0	aralkylamino compound; imidazoles	human metabolite; mouse metabolite; neurotransmitter
homogentisic acid Homogentisic Acid: Dihydroxyphenylacetic acid with hydroxyls at the 2 and 5 positions of the phenyl ring.. homogentisic acid : A dihydroxyphenylacetic acid having the two hydroxy substituents at the 2- and 5-positions.	2	1	0	dihydroxyphenylacetic acid; hydroquinones	human metabolite; plant metabolite
hydroquinone [no description available]	2.06	1	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.	2.02	1	0	indole-3-acetic acids; monocarboxylic acid	auxin; human metabolite; mouse metabolite; plant hormone; plant metabolite
thioctic acid Thioctic Acid: An octanoic acid bridged with two sulfurs so that it is sometimes also called a pentanoic acid in some naming schemes. It is biosynthesized by cleavage of LINOLEIC ACID and is a coenzyme of oxoglutarate dehydrogenase (KETOGLUTARATE DEHYDROGENASE COMPLEX). It is used in DIETARY SUPPLEMENTS.	2.49	2	0	dithiolanes; heterocyclic fatty acid; thia fatty acid	fundamental metabolite; geroprotector
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	2.42	2	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
nitrites Nitrites: Salts of nitrous acid or compounds containing the group NO2-. The inorganic nitrites of the type MNO2 (where M=metal) are all insoluble, except the alkali nitrites. The organic nitrites may be isomeric, but not identical with the corresponding nitro compounds. (Grant & Hackh's Chemical Dictionary, 5th ed)	2.72	3	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species	human metabolite
phenol [no description available]	3.35	6	0	phenols	antiseptic drug; disinfectant; human xenobiotic metabolite; mouse metabolite
phenylacetic acid phenylacetic acid : A monocarboxylic acid that is toluene in which one of the hydrogens of the methyl group has been replaced by a carboxy group.	2.46	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
pyridoxine 4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol: structure in first source. vitamin B6 : Any member of the group of pyridines that exhibit biological activity against vitamin B6 deficiency. Vitamin B6 deficiency is associated with microcytic anemia, electroencephalographic abnormalities, dermatitis with cheilosis (scaling on the lips and cracks at the corners of the mouth) and glossitis (swollen tongue), depression and confusion, and weakened immune function. Vitamin B6 consists of the vitamers pyridoxine, pyridoxal, and pyridoxamine and their respective 5'-phosphate esters (and includes their corresponding ionized and salt forms).	2.08	1	0	hydroxymethylpyridine; methylpyridines; monohydroxypyridine; vitamin B6	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae 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.	2.03	1	0	2-oxo monocarboxylic acid	cofactor; fundamental metabolite
thiosulfates Thiosulfates: Inorganic salts of thiosulfuric acid possessing the general formula R2S2O3.. thiosulfate(2-) : A divalent inorganic anion obtained by removal of both protons from thiosulfuric acid.	2	1	0	divalent inorganic anion; sulfur oxide; sulfur oxoanion	human metabolite
dithionite Dithionite: Dithionite. The dithionous acid ion and its salts.	2.04	1	0	sulfur oxide; sulfur oxoanion
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.	2.03	1	0	alpha,omega-dicarboxylic acid; C4-dicarboxylic acid	anti-ulcer drug; fundamental metabolite; micronutrient; nutraceutical; radiation protective agent
sulfuric acid sulfuric acid : A sulfur oxoacid that consists of two oxo and two hydroxy groups joined covalently to a central sulfur atom.	2.21	1	0	sulfur oxoacid	catalyst
urea pseudourea: clinical use; structure. isourea : A carboximidic acid that is the imidic acid tautomer of urea, H2NC(=NH)OH, and its hydrocarbyl derivatives.	2.06	1	0	isourea; monocarboxylic acid amide; one-carbon compound	Daphnia magna metabolite; Escherichia coli metabolite; fertilizer; flour treatment agent; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
vanillin Vanilla: A plant genus of the family ORCHIDACEAE that is the source of the familiar flavoring used in foods and medicines (FLAVORING AGENTS).	2.48	2	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.	1.99	1	0	xanthine	Saccharomyces cerevisiae metabolite
catechin [no description available]	2.03	1	0	hydroxyflavan
menthol Menthol: A monoterpene cyclohexanol produced from mint oils.	2.6	1	0	p-menthane monoterpenoid; secondary alcohol	volatile oil component
1-anilino-8-naphthalenesulfonate 1-anilino-8-naphthalenesulfonate: RN given refers to parent cpd. 8-anilinonaphthalene-1-sulfonic acid : A naphthalenesulfonic acid that is naphthalene-1-sulfonic acid substituted by a phenylamino group at position 8.	3.17	5	0	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
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.	4.38	7	0	guaiacols; monocarboxylic acid	human metabolite; mouse metabolite
7,8-dihydroxyflavone 7,8-dihydroxyflavone : A dihydroxyflavone that is flavone substituted by hydroxy groups at positions 7 and 8. A dihydroxyflavone that is flavone substituted by hydroxy groups at positions 7 and 8. A naturally occurring flavonoid produced by several plants, including the weed Tridax procumbens (coalbuttons or tridax daisy) and the tree Godmania aesculifolia, In animal models, it has shown efficacy against several diseases of the nervous system, including Alzheimer's, Parkinson's, and Huntington's.	2.25	1	0	dihydroxyflavone	antidepressant; antineoplastic agent; antioxidant; plant metabolite; tropomyosin-related kinase B receptor agonist
2,2'-azobis(2-amidinopropane) 2,2'-azobis(2-amidinopropane): water-soluble free-radical initiator	2.25	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.	2.1	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)	2.46	2	0	monocarboxylic acid amide; sulfonamide; thiadiazoles	anticonvulsant; diuretic; EC 4.2.1.1 (carbonic anhydrase) inhibitor
benserazide Benserazide: An inhibitor of DOPA DECARBOXYLASE that does not enter the central nervous system. It is often given with LEVODOPA in the treatment of parkinsonism to prevent the conversion of levodopa to dopamine in the periphery, thereby increasing the amount that reaches the central nervous system and reducing the required dose. It has no antiparkinson actions when given alone.. benserazide : A carbohydrazide that results from the formal condensation of the carboxy group of DL-serine with the primary amino group of 4-(hydrazinylmethyl)benzene-1,2,3-triol. An aromatic-L-amino-acid decarboxylase inhibitor (DOPA decarboxylase inhibitor) that does not enter the central nervous system, it is used as its hydrochloride salt as an adjunct to levodopa in the treatment of parkinsonism. By preventing the conversion of levodopa to dopamine in the periphery, it causes an increase in the amount of levodopa reaching the central nervous system and so reduces the required dose. Benserazide has no antiparkinson actions when given alone.	1.96	1	0	carbohydrazide; catechols; primary alcohol; primary amino compound	antiparkinson drug; dopaminergic agent; EC 4.1.1.28 (aromatic-L-amino-acid decarboxylase) inhibitor
berberine [no description available]	2.57	2	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
busulfan [no description available]	2.25	1	0	methanesulfonate ester	alkylating agent; antineoplastic agent; carcinogenic agent; insect sterilant; teratogenic agent
camphor, (+-)-isomer [no description available]	2.6	1	0	bornane monoterpenoid; cyclic monoterpene ketone	plant metabolite
carprofen carprofen: RN given refers to cpd without isomeric designation. carprofen : Propanoic acid in which one of the methylene hydrogens is substituted by a 6-chloro-9H-carbazol-2-yl group. A non-steroidal anti-inflammatory drug, it is no longer used in human medicine but is still used for treatment of arthritis in elderly dogs.	2.21	1	0	carbazoles; organochlorine compound	EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-steroidal anti-inflammatory drug; photosensitizing agent
chloroxine chloroxine : A monohydroxyquinoline that is quinolin-8-ol in which the hydrogens at positions 5 and 7 have been substituted by chlorine. A synthetic antibacterial prepared by chlorination of quinolin-8-ol, it is used for the treatment of dandruff and seborrhoeic dermatitis of the scalp.	3.51	1	0	monohydroxyquinoline; organochlorine compound	antibacterial agent; antifungal drug; antiseborrheic
decanoic acid decanoate : A fatty acid anion 10:0 that is the conjugate base of decanoic acid.. decanoic acid : A C10, straight-chain saturated fatty acid.	2.11	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; anti-inflammatory agent; antibacterial agent; human metabolite; plant metabolite; volatile oil component
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.	2.13	1	0	alpha-amino acid; fluoroamino acid	trypanocidal 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.	2.07	1	0	diester; phthalate ester	EC 3.2.1.20 (alpha-glucosidase) inhibitor; environmental contaminant; metabolite; plasticiser; teratogenic agent
disulfiram [no description available]	3.51	1	0	organic disulfide; organosulfur acaricide	angiogenesis inhibitor; antineoplastic agent; apoptosis inducer; EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor; EC 3.1.1.1 (carboxylesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 5.99.1.2 (DNA topoisomerase) inhibitor; ferroptosis inducer; fungicide; NF-kappaB inhibitor
ebselen ebselen : A benzoselenazole that is 1,2-benzoselenazol-3-one carrying an additional phenyl substituent at position 2. Acts as a mimic of glutathione peroxidase.	3.51	1	0	benzoselenazole	anti-inflammatory drug; antibacterial agent; anticoronaviral agent; antifungal agent; antineoplastic agent; antioxidant; apoptosis inducer; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor; EC 2.5.1.7 (UDP-N-acetylglucosamine 1-carboxyvinyltransferase) inhibitor; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor; EC 3.1.3.25 (inositol-phosphate phosphatase) inhibitor; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; EC 3.5.4.1 (cytosine deaminase) inhibitor; EC 5.1.3.2 (UDP-glucose 4-epimerase) inhibitor; enzyme mimic; ferroptosis inhibitor; genotoxin; hepatoprotective agent; neuroprotective agent; radical scavenger
ether Ether: A mobile, very volatile, highly flammable liquid used as an inhalation anesthetic and as a solvent for waxes, fats, oils, perfumes, alkaloids, and gums. It is mildly irritating to skin and mucous membranes.. ether : An organooxygen compound with formula ROR, where R is not hydrogen.. diethyl ether : An ether in which the oxygen atom is linked to two ethyl groups.	2.43	2	0	ether; volatile organic compound	inhalation anaesthetic; non-polar solvent; refrigerant
fenofibrate Pharmavit: a polyvitamin product, comprising vitamins A, D2, B1, B2, B6, C, E, nicotinamide, & calcium pantothene; may be a promising agent for application to human populations exposed to carcinogenic and genetic hazards of ionizing radiation; RN from CHEMLINE	2.15	1	0	aromatic ether; chlorobenzophenone; isopropyl ester; monochlorobenzenes	antilipemic drug; environmental contaminant; geroprotector; xenobiotic
fluconazole Fluconazole: Triazole antifungal agent that is used to treat oropharyngeal CANDIDIASIS and cryptococcal MENINGITIS in AIDS.. fluconazole : A member of the class of triazoles that is propan-2-ol substituted at position 1 and 3 by 1H-1,2,4-triazol-1-yl groups and at position 2 by a 2,4-difluorophenyl group. It is an antifungal drug used for the treatment of mucosal candidiasis and for systemic infections including systemic candidiasis, coccidioidomycosis, and cryptococcosis.	2.55	2	0	conazole antifungal drug; difluorobenzene; tertiary alcohol; triazole antifungal drug	environmental contaminant; P450 inhibitor; xenobiotic
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.	2.15	1	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
2-propanol 2-Propanol: An isomer of 1-PROPANOL. It is a colorless liquid having disinfectant properties. It is used in the manufacture of acetone and its derivatives and as a solvent. Topically, it is used as an antiseptic.. propan-2-ol : A secondary alcohol that is propane in which one of the hydrogens attached to the central carbon is substituted by a hydroxy group.	2.08	1	0	secondary alcohol; secondary fatty alcohol	protic solvent
kojic acid [no description available]	2.17	1	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
beta-lapachone beta-lapachone: antineoplastic inhibitor of reverse transcriptase, DNA topoisomerase, and DNA polymerase. beta-lapachone : A benzochromenone that is 3,4-dihydro-2H-benzo[h]chromene-5,6-dione substituted by geminal methyl groups at position 2. Isolated from Tabebuia avellanedae, it exhibits antineoplastic and anti-inflammatory activities.	3.51	1	0	benzochromenone; orthoquinones	anti-inflammatory agent; antineoplastic agent; plant metabolite
methyl methanesulfonate [no description available]	2.25	1	0	methanesulfonate ester	alkylating agent; apoptosis inducer; carcinogenic agent; genotoxin; mutagen
niclosamide Niclosamide: An antihelmintic that is active against most tapeworms. (From Martindale, The Extra Pharmacopoeia, 30th ed, p48). niclosamide : A secondary carboxamide resulting from the formal condensation of the carboxy group of 5-chlorosalicylic acid with the amino group of 2-chloro-4-nitroaniline. It is an oral anthelmintic drug approved for use against tapeworm infections.	2.15	1	0	benzamides; C-nitro compound; monochlorobenzenes; salicylanilides; secondary carboxamide	anthelminthic drug; anticoronaviral agent; antiparasitic agent; apoptosis inducer; molluscicide; piscicide; STAT3 inhibitor
nifedipine Nifedipine: A potent vasodilator agent with calcium antagonistic action. It is a useful anti-anginal agent that also lowers blood pressure.	2.02	1	0	C-nitro compound; dihydropyridine; methyl ester	calcium channel blocker; human metabolite; tocolytic agent; vasodilator agent
octopamine Octopamine: An alpha-adrenergic sympathomimetic amine, biosynthesized from tyramine in the CNS and platelets and also in invertebrate nervous systems. It is used to treat hypotension and as a cardiotonic. The natural D(-) form is more potent than the L(+) form in producing cardiovascular adrenergic responses. It is also a neurotransmitter in some invertebrates.. octopamine : A member of the class of phenylethanolamines that is phenol which is substituted at the para- position by a 2-amino-1-hydroxyethyl group. A biogenic phenylethanolamine which has been found to act as a neurotransmitter, neurohormone or neuromodulator in invertebrates.	1.96	1	0	phenylethanolamines; tyramines	neurotransmitter
pentoxifylline [no description available]	2.13	1	0	oxopurine
phloretin [no description available]	2.11	1	0	dihydrochalcones	antineoplastic agent; plant 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
sulfanilamide [no description available]	2.46	2	0	substituted aniline; sulfonamide antibiotic; sulfonamide	antibacterial agent; drug allergen; EC 4.2.1.1 (carbonic anhydrase) inhibitor
tyramine [no description available]	5.25	4	1	monoamine molecular messenger; primary amino compound; tyramines	EC 3.1.1.8 (cholinesterase) inhibitor; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter
zonisamide Zonisamide: A benzisoxazole and sulfonamide derivative that acts as a CALCIUM CHANNEL blocker. It is used primarily as an adjunctive antiepileptic agent for the treatment of PARTIAL SEIZURES, with or without secondary generalization.. zonisamide : A 1,2-benzoxazole compound having a sulfamoylmethyl substituent at the 3-position.	2.46	2	0	1,2-benzoxazoles; sulfonamide	anticonvulsant; antioxidant; central nervous system drug; protective agent; T-type calcium channel blocker
prednisolone Prednisolone: A glucocorticoid with the general properties of the corticosteroids. It is the drug of choice for all conditions in which routine systemic corticosteroid therapy is indicated, except adrenal deficiency states.. prednisolone : A glucocorticoid that is prednisone in which the oxo group at position 11 has been reduced to the corresponding beta-hydroxy group. It is a drug metabolite of prednisone.	2.13	1	0	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	adrenergic agent; anti-inflammatory drug; antineoplastic agent; drug metabolite; environmental contaminant; immunosuppressive agent; xenobiotic
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.	2.04	1	0	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
aspartic acid Aspartic Acid: One of the non-essential amino acids commonly occurring in the L-form. It is found in animals and plants, especially in sugar cane and sugar beets. It may be a neurotransmitter.. aspartic acid : An alpha-amino acid that consists of succinic acid bearing a single alpha-amino substituent. L-aspartic acid : The L-enantiomer of aspartic acid.	2	1	0	aspartate family amino acid; aspartic acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; mouse metabolite; neurotransmitter
sucrose Saccharum: A plant genus of the family POACEAE widely cultivated in the tropics for the sweet cane that is processed into sugar.	2.72	2	0	glycosyl glycoside	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; sweetening agent
uridine diphosphate Uridine Diphosphate: A uracil nucleotide containing a pyrophosphate group esterified to C5 of the sugar moiety.	2.72	2	0	pyrimidine ribonucleoside 5'-diphosphate; uridine 5'-phosphate	Escherichia coli metabolite; mouse metabolite
galactose galactopyranose : The pyranose form of galactose.	2.15	1	0	D-galactose; galactopyranose	Escherichia coli metabolite; mouse metabolite
levodopa Levodopa: The naturally occurring form of DIHYDROXYPHENYLALANINE and the immediate precursor of DOPAMINE. Unlike dopamine itself, it can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to DOPAMINE. It is used for the treatment of PARKINSONIAN DISORDERS and is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system.. L-dopa : An optically active form of dopa having L-configuration. Used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease	2.47	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
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.	17.69	413	14	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.	6.19	16	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
phlorhizin [no description available]	2.48	2	0	aryl beta-D-glucoside; dihydrochalcones; monosaccharide derivative	antioxidant; plant metabolite
4-toluenesulfonic acid 4-toluenesulfonic acid: RN given refers to parent cpd; other RNs in 9th CI Form Index. toluene-4-sulfonic acid : An arenesulfonic acid that is benzenesulfonic acid in which the hydrogen at position 4 is replaced by a methyl group.	2.04	1	0	arenesulfonic acid; toluenes
lactose Lactose: A disaccharide of GLUCOSE and GALACTOSE in human and cow milk. It is used in pharmacy for tablets, in medicine as a nutrient, and in industry.. lactose : A glycosylglucose disaccharide, found most notably in milk, that consists of D-galactose and D-glucose fragments bonded through a beta-1->4 glycosidic linkage. The glucose fragment can be in either the alpha- or beta-pyranose form, whereas the galactose fragment can only have the beta-pyranose form.. beta-lactose : The beta-anomer of lactose.	2.15	1	0	lactose
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.	2.43	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
n-hexanal [no description available]	2.03	1	0	medium-chain fatty aldehyde; n-alkanal; saturated fatty aldehyde	human urinary metabolite
barbituric acid barbituric acid: RN given refers to parent cpd; structure from Merck Index, 9th ed, #966. barbituric acid : A barbiturate, the structure of which is that of perhydropyrimidine substituted at C-2, -4 and -6 by oxo groups. Barbituric acid is the parent compound of barbiturate drugs, although it is not itself pharmacologically active.	1.94	1	0	barbiturates	allergen; xenobiotic
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.	2.08	1	0	chloromethanes; one-carbon compound	carcinogenic agent; central nervous system drug; inhalation anaesthetic; non-polar solvent; refrigerant
n-pentanol n-pentanol: RN given refers to parent cpd. pentan-1-ol : A short-chain primary fatty alcohol that is pentane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It has been isolated from Melicope ptelefolia.	2.15	1	0	pentanol; short-chain primary fatty alcohol	human metabolite; plant metabolite
tryptophan Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3.	2.21	1	0	erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; tryptophan zwitterion; tryptophan	antidepressant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
methylamine methyl group : An alkyl group that is the univalent group derived from methane by removal of a hydrogen atom.	1.93	1	0	methylamines; one-carbon compound; primary aliphatic amine	mouse metabolite
tert-butyl alcohol tert-Butyl Alcohol: An isomer of butanol that contains a tertiary butyl group that consists of three methyl groups, each separately attached to a central (tertiary) carbon.. tert-butanol : A tertiary alcohol alcohol that is isobutane substituted by a hydroxy group at position 2.	2	1	0	tertiary alcohol	human xenobiotic metabolite
acrylamide [no description available]	2.21	1	0	acrylamides; N-acylammonia; primary carboxamide	alkylating agent; carcinogenic agent; Maillard reaction product; mutagen; neurotoxin
diisobutyl phthalate diisobutyl phthalate : A phthalate ester that is the diester obtained by the formal condensation of the carboxy groups of phthalic acid with two molecules of isobutanol.	2.07	1	0	diester; phthalate ester	plasticiser; PPAR modulator; teratogenic agent
isatin tribulin: endogenous MONOAMINE OXIDASE inhibitory activity extractable into ethyl acetate found in brain and many mammalian tissues and fluids; ISATIN is a major component; produced in excess following alcohol withdrawal;	1.98	1	0	indoledione	EC 1.4.3.4 (monoamine oxidase) inhibitor; plant metabolite
diphenyl diphenyl: RN given refers to unlabeled cpd; structure	2.21	1	0	aromatic fungicide; benzenes; biphenyls	antifungal agrochemical; antimicrobial food preservative
proflavine Proflavine: Topical antiseptic used mainly in wound dressings.. 3,6-diaminoacridine : An aminoacridine that is acridine that is substituted by amino groups at positions 3 and 6. A slow-acting bacteriostat that is effective against many Gram-positive bacteria (but ineffective against spores), its salts were formerly used for treatment of burns and infected wounds.	3.51	1	0	aminoacridines	antibacterial agent; antiseptic drug; carcinogenic agent; chromophore; intercalator
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)	2.72	3	0	benzoate ester; paraben; phenols	antifungal agent; antimicrobial agent
2,4-di-tert-butylphenol 2,4-di-tert-butylphenol: structure given in first source. 2,4-di-tert-butylphenol : A member of the class of phenols carrying two tert-butyl substituents at positions 2 and 4.	2.6	1	0	alkylbenzene; phenols	antioxidant; bacterial metabolite; marine metabolite
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.	1.99	1	0	aldehyde; furans	Maillard reaction product; metabolite
4-hydroxyacetophenone 4-hydroxyacetophenone: promotes secretion of bile & bile salts, which promotes griseofulvin absorption in the duodenum. 4'-hydroxyacetophenone : A monohydroxyacetophenone carrying a hydroxy substituent at position 4'.	2.47	2	0	monohydroxyacetophenone	fungal metabolite; mouse metabolite; 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.	3.17	5	0	methoxybenzoic acid; monohydroxybenzoic acid	plant metabolite
uridine diphosphate glucose Uridine Diphosphate Glucose: A key intermediate in carbohydrate metabolism. Serves as a precursor of glycogen, can be metabolized into UDPgalactose and UDPglucuronic acid which can then be incorporated into polysaccharides as galactose and glucuronic acid. Also serves as a precursor of sucrose lipopolysaccharides, and glycosphingolipids.. UDP-alpha-D-glucose : The alpha-anomer of UDP-alpha-D-glucose. It is used in nucleotide sugars metabolism.	2.17	1	0	UDP-D-glucose	fundamental metabolite
ethyl acetate ethyl acetate : The acetate ester formed between acetic acid and ethanol.	2.48	2	0	acetate ester; ethyl ester; volatile organic compound	EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor; metabolite; polar aprotic solvent; Saccharomyces cerevisiae metabolite
catechin Catechin: An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.. catechin : Members of the class of hydroxyflavan that have a flavan-3-ol skeleton and its substituted derivatives.. rac-catechin : A racemate comprising equimolar amounts of (+)- and (-)-catechin. (+)-catechin : The (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite.	3.67	9	0	catechin	antioxidant; plant metabolite
cyclopentane Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.	2.49	2	0	cycloalkane; cyclopentanes; volatile organic compound	non-polar solvent
isoxazoles Isoxazoles: Azoles with an OXYGEN and a NITROGEN next to each other at the 1,2 positions, in contrast to OXAZOLES that have nitrogens at the 1,3 positions.. isoxazole : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing three carbon atoms and an oxygen and nitrogen atom adjacent to each other. It is the parent of the class of isoxazoles.. isoxazoles : Oxazoles in which the N and O atoms are adjacent.	2.31	1	0	isoxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
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.	2.11	1	0	hydroxy monocarboxylic acid	plant metabolite
oleanolic acid [no description available]	2.6	1	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	plant metabolite
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.	2.17	1	0	3'-hydroxyflavanones; 4'-methoxyflavanones; dihydroxyflavanone; disaccharide derivative; flavanone glycoside; monomethoxyflavanone; rutinoside	mutagen
tryptophol tryptophol : An indolyl alcohol that is ethanol substituted by a 1H-indol-3-yl group at position 2.	5.33	9	0	indolyl alcohol	auxin; plant metabolite; Saccharomyces cerevisiae metabolite
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.	2.05	1	0	methoxybenzenes; phenols
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.	2.97	4	0	dialdehyde	biomarker
lignoceric acid lignoceric acid: RN given refers to parent cpd; structure. tetracosanoic acid : A C24 straight-chain saturated fatty acid.	2.03	1	0	straight-chain saturated fatty acid; very long-chain fatty acid	Daphnia tenebrosa metabolite; human metabolite; plant metabolite; volatile oil component
3-hydroxyflavone 3-hydroxyflavone: structure given in first source. flavonol : A monohydroxyflavone that is the 3-hydroxy derivative of flavone.	2.47	2	0	flavonols; monohydroxyflavone
dansyl chloride dansyl chloride: RN given refers to unlabeled cpd	2.15	1	0	aminonaphthalene; sulfonic acid derivative
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.	2.02	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.	2.44	2	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
3-hydroxybenzeneacetic acid 3-hydroxybenzeneacetic acid: metabolite of L-dopa; structure. 3-hydroxyphenylacetic acid : A monocarboxylic acid that is phenylacetic acid in which the hydrogen at position 3 on the benzene ring is replaced by a hydroxy group.	2.02	1	0	monocarboxylic acid; phenols	human xenobiotic metabolite
isovanillic acid 3-hydroxy-4-methoxybenzoic acid : A methoxybenzoic acid that is 4-methoxybenzoic acid bearing a hydroxy substituent at position 3.	2.07	1	0	methoxybenzoic acid; monohydroxybenzoic acid	antibacterial agent; plant metabolite
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).	2.55	2	0
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.	4.82	7	1	alpha-tocopherol	algal metabolite; antiatherogenic agent; anticoagulant; antioxidant; antiviral agent; EC 2.7.11.13 (protein kinase C) inhibitor; immunomodulator; micronutrient; nutraceutical; plant metabolite
tocopherols [no description available]	2.31	1	0
isobarbaloin aloin B : A C-glycosyl compound that is beta-D-glucopyranose in which the anomeric hydroxy group is replaced by a 4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9,10-dihydroanthracen-9-yl moiety (the 9R diastereoisomer).	3.51	1	0	anthracenes; C-glycosyl compound; cyclic ketone; phenols	laxative; metabolite
3-methoxy-4-hydroxyphenylethanol 3-Methoxy-4-hydroxyphenylethanol: Metabolite of serotonin and norepinephrine.	2.31	1	0	methoxybenzenes; phenols
2,2-bis(bromomethyl)-1,3-propanediol 2,2-bis(bromomethyl)-1,3-propanediol: structure given in first source	2.72	2	0	primary alcohol
streptomycin [no description available]	2.05	1	0	antibiotic antifungal drug; antibiotic fungicide; streptomycins	antibacterial drug; antifungal agrochemical; antimicrobial agent; antimicrobial drug; bacterial metabolite; protein synthesis inhibitor
carbonates Carbonates: Salts or ions of the theoretical carbonic acid, containing the radical CO2(3-). Carbonates are readily decomposed by acids. The carbonates of the alkali metals are water-soluble; all others are insoluble. (From Grant & Hackh's Chemical Dictionary, 5th ed). carbonates : Organooxygen compounds that are salts or esters of carbonic acid, H2CO3.	2.13	1	0	carbon oxoanion
raspberry ketone rheosmin: an NSAID that blocks NF-kappaB activation; isolated from Pinus densiflora; structure in first source. raspberry ketone : A ketone that is 4-phenylbutan-2-one in which the phenyl ring is substituted at position 4 by a hydroxy group. It is found in a variety of fruits including raspberries, blackberries and cranberries, and is used in perfumery and cosmetics.	2.6	1	0	methyl ketone; phenols	androgen antagonist; cosmetic; flavouring agent; fragrance; hepatoprotective agent; metabolite
molybdenum Molybdenum: A metallic element with the atomic symbol Mo, atomic number 42, and atomic weight 95.95. It is an essential trace element, being a component of the enzymes xanthine oxidase, aldehyde oxidase, and nitrate reductase.	2.15	1	0	chromium group element atom	micronutrient
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.	2.49	2	0	titanium group element 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.	2.21	1	0	copper group element atom; elemental gold
sodium thiosulfate sodium thiosulfate: do not confuse synonym sodium hyposulfite with sodium hyposulfite, synonym for di-Na salt of dithionous acid. sodium thiosulfate : An inorganic sodium salt composed of sodium and thiosulfate ions in a 2:1 ratio.	2	1	0	inorganic sodium salt	antidote to cyanide poisoning; antifungal drug; nephroprotective agent
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	2.43	2	0	dihydrogen
galactose aldohexose : A hexose with a (potential) aldehyde group at one end.	3	1	0
ozone Ozone: The unstable triatomic form of oxygen, O3. It is a powerful oxidant that is produced for various chemical and industrial uses. Its production is also catalyzed in the ATMOSPHERE by ULTRAVIOLET RAY irradiation of oxygen or other ozone precursors such as VOLATILE ORGANIC COMPOUNDS and NITROGEN OXIDES. About 90% of the ozone in the atmosphere exists in the stratosphere (STRATOSPHERIC OZONE).. ozone : An elemental molecule with formula O3. An explosive, pale blue gas (b.p. -112degreeC) that has a characteristic, pungent odour, it is continuously produced in the upper atmosphere by the action of solar ultraviolet radiation on atmospheric oxygen. It is an antimicrobial agent used in the production of bottled water, as well as in the treatment of meat, poultry and other foodstuffs.	2.04	1	0	elemental molecule; gas molecular entity; reactive oxygen species; triatomic oxygen	antiseptic drug; disinfectant; electrophilic reagent; greenhouse gas; mutagen; oxidising agent; tracer
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.	2.04	1	0	titanium oxides	food colouring
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.	2.44	2	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
ochracin ochracin: produced by Aspergillus alutaceus; structure in first source	2.15	1	0	isochromanes
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.	3.39	6	0	benzenes; phenyl acetates
4-ethylphenol 4-ethylphenol: RN given refers to parent cpd. 4-ethylphenol : A member of the class of phenols carrying an ethyl substituent at position 4.	2.9	4	0	phenols	fungal xenobiotic metabolite
isopentyl alcohol isopentyl alcohol: RN given refers to unlabeled parent cpd. isoamylol : An primary alcohol that is butan-1-ol in which a hydrogen at position 3 has been replaced by a methyl group.	2.15	1	0	alkyl alcohol; primary alcohol; volatile organic compound	antifungal agent; Saccharomyces cerevisiae metabolite; xenobiotic metabolite
1,4-dioxane 1,4-dioxane: dehydrating agent; polar solvent miscible both with water & most organic solvents. dioxane : Any member of the class of dioxanes that is a cyclohexane in which two carbon atoms are replaced by oxygen atoms.. 1,4-dioxane : A dioxane with oxygen atoms at positions 1 and 4.	2.02	1	0	dioxane; volatile organic compound	carcinogenic agent; metabolite; NMR chemical shift reference compound; non-polar solvent
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.	2.05	1	0	phenols	antioxidant; ferroptosis inhibitor; food additive; geroprotector
alkenes [no description available]	2.02	1	0
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.	2	1	0	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
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).	2.72	2	0	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
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.	2.08	1	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.	2.03	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]	2.04	1	0	chromanol; monocarboxylic acid; phenols	antioxidant; ferroptosis inhibitor; neuroprotective agent; radical scavenger; Wnt signalling inhibitor
itraconazole Itraconazole: A triazole antifungal agent that inhibits cytochrome P-450-dependent enzymes required for ERGOSTEROL synthesis.. itraconazole : An N-arylpiperazine that is cis-ketoconazole in which the imidazol-1-yl group is replaced by a 1,2,4-triazol-1-yl group and in which the actyl group attached to the piperazine moiety is replaced by a p-[(+-)1-sec-butyl-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl]phenyl group. A potent P-glycoprotein and CYP3A4 inhibitor, it is used as an antifungal drug for the treatment of various fungal infections, including aspergillosis, blastomycosis, candidiasis, chromoblastomycosis, coccidioidomycosis, cryptococcosis, histoplasmosis, and sporotrichosis.	2.11	1	0	aromatic ether; conazole antifungal drug; cyclic ketal; dichlorobenzene; dioxolane; N-arylpiperazine; triazole antifungal drug; triazoles	EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor; Hedgehog signaling pathway inhibitor; P450 inhibitor
zileuton [no description available]	2.1	1	0	1-benzothiophenes; ureas	anti-asthmatic drug; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; ferroptosis inhibitor; leukotriene antagonist; non-steroidal anti-inflammatory drug
urea formaldehyde foam urea formaldehyde foam: widely used foam insulation	2.06	1	0
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.	7.66	58	0	D-glucopyranose	epitope; mouse metabolite
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.	2.44	2	0	flavans; gallate ester; polyphenol	antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite
gallocatechol gallocatechol: structure give in first source; RN given for (trans-(+-))-omer; inhibits DNA-dependent DNA & RNA polymerases. (+)-gallocatechin : A gallocatechin that has (2R,3S)-configuration. It is found in green tea and bananas.. gallocatechin : A catechin that is a flavan substituted by hydroxy groups at positions 3, 3', 4', 5, 5' and 7 (the trans isomer). It is isolated from Acacia mearnsii.	2.05	1	0	gallocatechin	antioxidant; metabolite; radical scavenger
peroxynitric acid [no description available]	2	1	0	nitrogen oxoacid
triazoles Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.	2.76	2	0	1,2,3-triazole
lupulon lupulon: antibiotic from hops; structure. lupulone : A beta-bitter acid in which the acyl group is specified as 3-methylbutanoyl.. beta-bitter acid : An alicyclic ketone obtained by prenylation at positions 4, 6 and 6 of any 2-acylphloroglucinol. beta-bitter acids are well known for their contribution to the bitter taste of beer.	3.19	1	0	beta-bitter acid	angiogenesis inhibitor; antimicrobial agent; antineoplastic agent; apoptosis inducer
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.	2.15	1	0	isocoumarins
indole-3-carboxylic acid indole-3-carboxylic acid : An indole-3-carboxylic acid carrying a carboxy group at position 3.	2.6	1	0	indol-3-yl carboxylic acid	bacterial metabolite; human metabolite
hesperetin [no description available]	2.17	1	0	3'-hydroxyflavanones; 4'-methoxyflavanones; monomethoxyflavanone; trihydroxyflavanone	antineoplastic agent; antioxidant; plant metabolite
eburicoic acid eburicoic acid: structure	2.06	1	0
3,4-dihydroxyphenylethanol 3,4-dihydroxyphenylethanol: serotonin metabolite; structure	14.82	139	13	catechols; primary alcohol	antineoplastic agent; antioxidant; metabolite
4-(hydroxyphenyl)acetamide 4-(hydroxyphenyl)acetamide: structure given in first source; an impurity found in the HPLC assay for atenolol; do not confuse with acetaminophen	2.46	2	0	acetamides
zinniol zinniol: phytotoxin isolated from cultures as of Alternaris spp. and Phoma macdonaldii; structure given in first source	2	1	0	methoxybenzenes
7-ketocholesterol 7-ketocholesterol: inhibits uptake of cholesterol in rabbit aorta. 7-ketocholesterol : A cholestanoid that consists of cholesterol bearing an oxo substituent at position 7.	2.05	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; 7-oxo steroid; cholestanoid	neuroprotective agent
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.	2.05	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.	2.05	1	0	amino acid zwitterion; homocysteine; serine family amino acid	fundamental metabolite; mouse metabolite
glucuronic acid Glucuronic Acid: A sugar acid formed by the oxidation of the C-6 carbon of GLUCOSE. In addition to being a key intermediate metabolite of the uronic acid pathway, glucuronic acid also plays a role in the detoxification of certain drugs and toxins by conjugating with them to form GLUCURONIDES.. D-glucuronic acid : The D-enantiomer of glucuronic acid.. D-glucopyranuronic acid : A D-glucuronic acid in cyclic pyranose form.	2.6	1	0	D-glucuronic acid	algal metabolite
phorbolol myristate acetate [no description available]	2.08	1	0
procyanidin Proanthocyanidins: Dimers and oligomers of flavan-3-ol units (CATECHIN analogs) linked mainly through C4 to C8 bonds to leucoanthocyanidins. They are structurally similar to ANTHOCYANINS but are the result of a different fork in biosynthetic pathways.	2.77	3	0	proanthocyanidin
parthenolide [no description available]	2.6	1	0	germacranolide
1-hexadecyl-2-acetyl-glycero-3-phosphocholine Platelet Activating Factor: A phospholipid derivative formed by PLATELETS; BASOPHILS; NEUTROPHILS; MONOCYTES; and MACROPHAGES. It is a potent platelet aggregating agent and inducer of systemic anaphylactic symptoms, including HYPOTENSION; THROMBOCYTOPENIA; NEUTROPENIA; and BRONCHOCONSTRICTION.. 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine : A 2-acetyl-1-alkyl-sn-glycero-3-phosphocholine betaine which has hexadecyl as the alkyl group. PAF is a potent phospholipid activator and mediator of many leukocyte functions, including platelet aggregation, inflammation, and anaphylaxis.	2.47	2	0	2-acetyl-1-alkyl-sn-glycero-3-phosphocholine	antihypertensive agent; beta-adrenergic antagonist; bronchoconstrictor agent; hematologic agent; vasodilator agent
tanshinone tanshinone: from root of Salvia miltiorrhiza Bunge; RN given refers to tanshinone I; cardioprotective agent and neuroprotective agent	3.51	1	0	abietane diterpenoid	anticoronaviral agent
3-chloro-4-hydroxyphenylacetic acid 3-chloro-4-hydroxyphenylacetic acid: RN given refers to parent cpd. (3-chloro-4-hydroxyphenyl)acetic acid : A hydroxy monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is replaced by a 3-chloro-4-hydroxyphenyl group. It is a major chlorinated metabolite of chlorotyrosine.	2.46	2	0	hydroxy monocarboxylic acid; monochlorobenzenes; phenols	mammalian metabolite
maculosin maculosin: RN refers to (3S-trans)-isomer; isolated from Alternaria alternata; structure given in first source. maculosin : A homodetic cyclic peptide that is a dipeptide composed of L-proline and L-tyrosine joined by peptide linkages.	2.05	1	0	dipeptide; homodetic cyclic peptide; phenols; pyrrolopyrazine	metabolite
5-s-cysteinyldopamine [no description available]	2.05	1	0	S-conjugate
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.	2.11	1	0	biflavonoid; hydroxyflavan; polyphenol; proanthocyanidin	antioxidant; metabolite
methotrexate [no description available]	2.25	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
xylose xylopyranose: structure in first source	2.17	1	0	D-xylose
paclitaxel 6-prenylnaringenin: from hop plant (Humulus lupulus): structure in first source. 6-prenylnaringenin : A trihydroxyflavanone having a structure of naringenin prenylated at C-6.	2.25	1	0	(2S)-flavan-4-one; 4'-hydroxyflavanones; trihydroxyflavanone	T-type calcium channel blocker
hydroxyl radical Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.	2.58	2	0	oxygen hydride; oxygen radical; reactive oxygen species
rhodioloside [no description available]	7.14	44	0	glycoside
malvidin malvidin: RN given refers to parent cpd; coloring agent from flowers of Malvaviscus conzatti. malvidin : An anthocyanidin cation that is delphinidin carrying methyl substituents at positions 3' and 5'.	2.15	1	0	5-hydroxyanthocyanidin	biological pigment; metabolite
singlet oxygen Singlet Oxygen: An excited state of molecular oxygen generated photochemically or chemically. Singlet oxygen reacts with a variety of biological molecules such as NUCLEIC ACIDS; PROTEINS; and LIPIDS; causing oxidative damages.	2.21	1	0	chalcogen; monoatomic oxygen; nonmetal atom	macronutrient
cryptotanshinone cryptotanshinone: from Salvia miltiorrhiza	3.51	1	0	abietane diterpenoid	anticoronaviral agent
fenton's reagent Fenton's reagent: used for oxidizing sugars & alcohols	2.44	2	0
syringopicroside syringopicroside: from leaves of Syringa oblata Lindl.; structure given in first source	1.96	1	0
tanshinone ii a tashinone IIA: a cardiovascular agent with antineoplastic activity; isolated from Salvia miltiorrhiza; structure in first source	3.51	1	0	abietane diterpenoid
elenolic acid elenolic acid: extract of olive plant; RN given refers to (2S-(2alpha,3alpha,4beta))-isomer; structure	4.2	6	0
2,5-dihydroxybenzyl alcohol 2,5-dihydroxybenzyl alcohol: structure; RN given refers to parent cpd. gentisyl alcohol : An aromatic primary alcohol that is benzyl alcohol substituted by hydroxy groups at positions 2 and 5.	2.06	1	0	aromatic primary alcohol; phenols	antineoplastic agent; antioxidant; apoptosis inhibitor; fungal metabolite
cholesterol alpha-oxide cholesterol alpha-oxide: RN given refers to (3beta,5alpha,6alpha)-isomer; structure	2	1	0	3beta-hydroxy steroid; epoxy steroid; oxysterol
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.	2.03	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.	1.99	1	0	arenecarbaldehyde; furans; primary alcohol	indicator; Maillard reaction product
lanosterol [no description available]	2.06	1	0	14alpha-methyl steroid; 3beta-sterol; tetracyclic triterpenoid	bacterial metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
methyl 3,4-dihydroxybenzoate [no description available]	3.51	1	0	catechols; methyl ester	antioxidant; neuroprotective agent; plant metabolite
wortmannin [no description available]	1.99	1	0	acetate ester; cyclic ketone; delta-lactone; organic heteropentacyclic compound	anticoronaviral agent; antineoplastic agent; autophagy inhibitor; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor; geroprotector; Penicillium metabolite; radiosensitizing agent
o-iodoxybenzoic acid o-iodoxybenzoic acid: structure in first source. 1-hydroxy-1,3-dioxobenziodoxole : A benziodoxole compound having hydroxy and oxo substituents at the 1-position and an oxo substituent at the 3-position. It is a mild and efficient hypervalent iodine synthetic reagent used to carry out several selective oxidation reactions.	2.04	1	0	benziodoxole	EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; oxidising agent
naringenin (S)-naringenin : The (S)-enantiomer of naringenin.	2.17	1	0	(2S)-flavan-4-one; naringenin	expectorant; plant metabolite
taxifolin (+)-taxifolin : A taxifolin that has (2R,3R)-configuration.	2.17	1	0	taxifolin	metabolite
alpha bitter acid humulon: antibiotic from hops; structure	3.19	1	0	aromatic ketone; cyclic ketone; diketone; tertiary alpha-hydroxy ketone; triol	antibacterial drug; antioxidant; cyclooxygenase 2 inhibitor; 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)	4.25	6	0
teprotide Teprotide: A synthetic nonapeptide (Pyr-Trp-Pro-Arg-Pro-Gln-Ile-Pro-Pro) which is identical to the peptide from the venom of the snake, Bothrops jararaca. It inhibits kininase II and ANGIOTENSIN I and has been proposed as an antihypertensive agent.	2.01	1	0	peptide
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	3.08	4	0	cyclodextrin
ergosterol [no description available]	2.76	3	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; ergostanoid; phytosterols	fungal metabolite; Saccharomyces cerevisiae 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.	2.05	1	0	butenedioic acid	food acidity regulator; fundamental metabolite; geroprotector
farnesol Farnesol: A colorless liquid extracted from oils of plants such as citronella, neroli, cyclamen, and tuberose. It is an intermediate step in the biological synthesis of cholesterol from mevalonic acid in vertebrates. It has a delicate odor and is used in perfumery. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). (2-trans,6-trans)-farnesol : The (2-trans,6-trans)-stereoisomer of farnesol.. farnesol : A farnesane sesquiterpenoid that is dodeca-2,6,10-triene substituted by methyl groups at positions 3, 7 and 11 and a hydroxy group at position 1.	6.67	20	0	farnesol	plant metabolite
resveratrol trans-resveratrol : A resveratrol in which the double bond has E configuration.	3.76	10	0	resveratrol	antioxidant; phytoalexin; plant metabolite; quorum sensing inhibitor; radical scavenger
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.	2.83	3	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.	4.61	7	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.	2.05	1	0	D-galactopyranuronic acid
lycopene [no description available]	2.03	1	0	acyclic carotene	antioxidant; plant metabolite
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).	5.99	33	0
gamma-sitosterol clionasterol : A member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3.	2.93	4	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; phytosterols	marine metabolite; plant metabolite
l 743,872 [no description available]	2.15	1	0
micafungin Micafungin: A cyclic lipo-hexapeptide echinocandin antifungal agent that is used for the treatment and prevention of CANDIDIASIS.. micafungin : A cyclic hexapeptide echinocandin antibiotic which exerts its effect by inhibiting the synthesis of 1,3-beta-D-glucan, an integral component of the fungal cell wall. It is used as the sodium salt for the treatment of invasive candidiasis, and of aspergillosis in patients who are intolerant of other therapy.	2.15	1	0	antibiotic antifungal drug; echinocandin	antiinfective agent
8-prenylnaringenin 8-prenylnaringenin: a phytogenic antineoplastic agent; structure in first source. sophoraflavanone B : A trihydroxyflavanone that is (S)-naringenin having a prenyl group at position 8.	3.65	2	0	(2S)-flavan-4-one; 4'-hydroxyflavanones; trihydroxyflavanone	plant metabolite; platelet aggregation inhibitor
2-methyl-5-(4-methylanilino)-1,3-benzothiazole-4,7-dione [no description available]	3.51	1	0	aminotoluene
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).	2.31	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
isoxanthohumol isoxanthohumol: structure in first source	3.65	2	0	flavanones
hydroxyphenethylferulate hydroxyphenethylferulate: from the roots of Atropa acuminata (Solanaceae); structure in first source	2.13	1	0	hydroxycinnamic 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.	4.06	14	0	4-coumaric acid	food component; mouse metabolite; plant metabolite
glycosides [no description available]	3.17	5	0
squalene Addavax: an oil-water nanoemulsion and adjuvant containing squalene, Tween 80, and sorbitane trioleate	2.96	4	0	triterpene	human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	4.02	13	0	stilbene
xanthohumol xanthohumol: from hop plant, Humulus lupulus. xanthohumol : A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 4, 2' and 4', a methoxy group at position 6' and a prenyl group at position 3'. Isolated from Humulus lupulus, it induces apoptosis in human malignant glioblastoma cells.	3.65	2	0	aromatic ether; chalcones; polyphenol	anti-HIV-1 agent; antineoplastic agent; antiviral agent; apoptosis inducer; EC 2.3.1.20 (diacylglycerol O-acyltransferase) inhibitor; metabolite
caffeic acid trans-caffeic acid : The trans-isomer of caffeic acid.	4.35	19	0	caffeic acid	geroprotector; mouse metabolite
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.	2.15	1	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
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.	2.47	2	0	cinnamate ester; tannin	food component; plant metabolite
thioguanine anhydrous Thioguanine: An antineoplastic compound which also has antimetabolite action. The drug is used in the therapy of acute leukemia.. tioguanine : A 2-aminopurine that is the 6-thiono derivative of 2-amino-1,9-dihydro-6H-purine. Incorporates into DNA and inhibits synthesis. Used in the treatment of leukaemia.	3.51	1	0	2-aminopurines	anticoronaviral agent; antimetabolite; antineoplastic 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.	2.31	1	0	thiocarboxamide	hepatotoxic agent
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)	4.09	5	0
4-hydroxyphenethylene glycol [no description available]	1.96	1	0	phenols
cytellin cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982	2.93	4	0
ovalbumin Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.	2.31	1	0
fraxetin fraxetin : A hydroxycoumarin that is 6-methoxycoumarin in which the hydrogens at positions 7 and 8 have been replaced by hydroxy groups.	3	1	0	aromatic ether; hydroxycoumarin	anti-inflammatory agent; antibacterial agent; antimicrobial agent; antioxidant; apoptosis inducer; apoptosis inhibitor; Arabidopsis thaliana metabolite; hepatoprotective agent; hypoglycemic agent
farnesoic acid farnesoic acid : A methyl-branched, trienoic fatty acid consisting of dodeca-2,6,10-trienoic acid having three methyl substituents at the 3-, 7- and 11-positions.. (2E,6E)-farnesoic acid : A farnesoic acid in which the double bonds at positions 2 and 6 both have E-configuration.	2.21	1	0	farnesoic acid	animal metabolite
quercetin [no description available]	5.06	12	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
dinoprostone prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.	3.46	7	0	prostaglandins E	human metabolite; mouse metabolite; oxytocic
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.	2.21	1	0	trihydroxyflavone	antineoplastic agent; metabolite
luteolin [no description available]	2.71	3	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
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.	2.48	2	0	octadecadienoic acid; omega-6 fatty acid	algal metabolite; Daphnia galeata metabolite; plant metabolite
scopoletin [no description available]	2.1	1	0	hydroxycoumarin	plant growth regulator; plant metabolite
leukotriene b4 Leukotriene B4: The major metabolite in neutrophil polymorphonuclear leukocytes. It stimulates polymorphonuclear cell function (degranulation, formation of oxygen-centered free radicals, arachidonic acid release, and metabolism). (From Dictionary of Prostaglandins and Related Compounds, 1990). leukotriene B4 : A leukotriene composed of (6Z,8E,10E,14Z)-icosatetraenoic acid having (5S)- and (12R)-hydroxy substituents. It is a lipid mediator of inflammation that is generated from arachidonic acid via the 5-lipoxygenase pathway.	2.01	1	0	dihydroxy monocarboxylic acid; hydroxy polyunsaturated fatty acid; leukotriene; long-chain fatty acid	human metabolite; mouse metabolite; plant metabolite; vasoconstrictor agent
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.	2.03	1	0	beta-D-glucoside; glycosyloxyflavone; monosaccharide derivative; trihydroxyflavone	antioxidant; plant metabolite
rosin rosin: Resin from plant. Do not confuse with the specific compound: 3-phenyl-2-propenyl-(E)-beta-D-glucopyranoside, also know as rosin.	3.84	3	0
apigetrin apigetrin: structure given in first source. apigenin 7-O-beta-D-glucoside : A glycosyloxyflavone that is apigenin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	2.21	1	0	beta-D-glucoside; dihydroxyflavone; glycosyloxyflavone; monosaccharide derivative	antibacterial agent; metabolite; non-steroidal anti-inflammatory drug
cholecalciferol Cholecalciferol: Derivative of 7-dehydroxycholesterol formed by ULTRAVIOLET RAYS breaking of the C9-C10 bond. It differs from ERGOCALCIFEROL in having a single bond between C22 and C23 and lacking a methyl group at C24.. calciol : A hydroxy seco-steroid that is (5Z,7E)-9,10-secocholesta-5,7,10(19)-triene in which the pro-S hydrogen at position 3 has been replaced by a hydroxy group. It is the inactive form of vitamin D3, being hydroxylated in the liver to calcidiol (25-hydroxyvitamin D3), which is then further hydroxylated in the kidney to give calcitriol (1,25-dihydroxyvitamin D3), the active hormone.	2	1	0	D3 vitamins; hydroxy seco-steroid; seco-cholestane; secondary alcohol; steroid hormone	geroprotector; human metabolite
rutin Hydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders.	2.98	4	0	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite
kaempferol [no description available]	3.6	2	0	7-hydroxyflavonol; flavonols; tetrahydroxyflavone	antibacterial agent; geroprotector; human blood serum metabolite; human urinary metabolite; human xenobiotic metabolite; plant metabolite
alpha-linolenic acid linolenic acid : A two-membered subclass of octadecatrienoic acid comprising the (9Z,12Z,15Z)- and (6Z,9Z,12Z)-isomers. Linolenic acids are nutrients essential to the formation of prostaglandins and are also used in making paints and synthetic resins.. linolenate : A polyunsaturated fatty acid anion obtained by deprotonation of the carboxy group of either alpha- or gamma-linolenic acid.	2.48	2	0	linolenic acid; omega-3 fatty acid	micronutrient; mouse metabolite; nutraceutical
genistein [no description available]	2.41	2	0	7-hydroxyisoflavones	antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; geroprotector; human urinary metabolite; phytoestrogen; plant metabolite; tyrosine kinase inhibitor
amphotericin b Amphotericin B: Macrolide antifungal antibiotic produced by Streptomyces nodosus obtained from soil of the Orinoco river region of Venezuela.. amphotericin B : A macrolide antibiotic used to treat potentially life-threatening fungal infections.	2.8	3	0	antibiotic antifungal drug; macrolide antibiotic; polyene antibiotic	antiamoebic agent; antiprotozoal drug; bacterial metabolite
jasmonic acid jasmonic acid: a derivative of alpha-linolenic acid that has a role in plant response to herbivory analogous to the role of prostanoids in inflammation in mammals;. jasmonic acid : An oxo monocarboxylic acid that is (3-oxocyclopentyl)acetic acid substituted by a (2Z)-pent-2-en-1-yl group at position 2 of the cyclopentane ring.	2.49	2	0	oxo monocarboxylic acid	jasmonates; plant metabolite
2-hexenal, z-isomer 2-hexenal: product of lipid peroxidation in the rat liver; a green odor chemical; do not confuse with the hexabarbital synonym, hexenal; RN given refers to cpd without isomeric designation. 2-hexenal : A hexenal having the double bond at the 2-position.. (2E)-hexenal : A 2-hexenal in which the olefinic double bond has E configuration. It occurs naturally in a wide range of fruits, vegetables, and spices.	2.05	1	0	2-hexenal	antibacterial agent; flavouring agent; plant metabolite
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.	2	1	0	hydroxycoumarin	antioxidant; plant metabolite; ultraviolet filter
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.	6.05	35	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
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.	2.11	1	0	beta-D-galactoside; monosaccharide derivative; quercetin O-glycoside; tetrahydroxyflavone	hepatoprotective agent; plant metabolite
myricetin [no description available]	2.17	1	0	7-hydroxyflavonol; hexahydroxyflavone	antineoplastic agent; antioxidant; cyclooxygenase 1 inhibitor; food component; geroprotector; hypoglycemic agent; plant metabolite
pterostilbene [no description available]	2.41	1	0	diether; methoxybenzenes; stilbenol	anti-inflammatory agent; antineoplastic agent; antioxidant; apoptosis inducer; hypoglycemic agent; neuroprotective agent; neurotransmitter; plant metabolite; radical scavenger
acteoside acteoside: a protein kinase C inhibitor with hepatoprotective, anti-asthmatic, and analgesic activities; a phenylethanoid glycoside related to isoacteoside; from leaves of Lippia multiflora (Verbenaceae). acteoside : A glycoside that is the alpha-L-rhamnosyl-(1->3)-beta-D-glucoside of hydroxytyrosol in which the hydroxy group at position 4 of the glucopyranosyl moiety has undergone esterification by formal condensation with trans-caffeic acid.	3.38	6	0	catechols; cinnamate ester; disaccharide derivative; glycoside; polyphenol	anti-inflammatory agent; antibacterial agent; antileishmanial agent; neuroprotective agent; plant metabolite
ellagic acid [no description available]	2.05	1	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
2,4-heptadienal 2,4-heptadienal: structure in first source. (E,E)-hepta-2,4-dienal : A heptadienal in which the two double bonds are located at positions 2 and 4 (the E,E-geoisomer).	2.05	1	0	heptadienal	flavouring agent
methyl linoleate [no description available]	2.21	1	0	fatty acid methyl ester	plant metabolite
topiramate Topiramate: A sulfamate-substituted fructose analog that was originally identified as a hypoglycemic agent. It is used for the treatment of EPILEPSY and MIGRAINE DISORDERS, and may also promote weight loss.. topiramate : A hexose derivative that is 2,3:4,5-di-O-isopropylidene-beta-D-fructopyranose in which the hydroxy group has been converted to the corresponding sulfamate ester. It blocks voltage-dependent sodium channels and is used as an antiepileptic and for the prevention of migraine.	2.46	2	0	cyclic ketal; ketohexose derivative; sulfamate ester	anticonvulsant; sodium channel blocker
herbimycin herbimycin: herbicidal antibiotic produced by Streptomyces sp.; see also herbimycin B; structure for herbimycin A in second source. herbimycin : A 19-membered macrocyle incorporating a benzoquinone ring and a lactam functionality. It is an ansamycin antibiotic that induces apoptosis and displays antitumour effects.	1.99	1	0	1,4-benzoquinones; lactam; macrocycle	antimicrobial agent; apoptosis inducer; herbicide; Hsp90 inhibitor; tyrosine kinase inhibitor
1,2-oleoylphosphatidylcholine 1,2-oleoylphosphatidylcholine: RN given refers to (Z,Z)-isomer. dioleoyl phosphatidylcholine : A phosphatidylcholine in which the phosphatidyl acyl groups are both oleoyl.	2.49	2	0	phosphatidylcholine(1+)
syringin syringin: a phenylpropanoid glycoside; see also eleutherosides & lyoniside for eleutheroside A: 474-58-8. syringin : A monosaccharide derivative that is trans-sinapyl alcohol attached to a beta-D-glucopyranosyl residue at position 1 via a glycosidic linkage.	2.06	1	0	beta-D-glucoside; dimethoxybenzene; monosaccharide derivative; primary alcohol	hepatoprotective agent; plant metabolite
andrographolide [no description available]	2.11	1	0	carbobicyclic compound; gamma-lactone; labdane diterpenoid; primary alcohol; secondary alcohol	anti-HIV agent; anti-inflammatory drug; antineoplastic agent; metabolite
ergosterol-5,8-peroxide ergosterol-5,8-peroxide: also inhibits sulfatase; isolated from fungus Cercospora kikuchii; structure given in first source. ergosterol peroxide : An ergostanoid that is ergosta-6,22-dien-3-ol with a peroxy group between positions 5 and 8 (the 3beta,5alpha,8alpha,22E stereoisomer). Isolated from Ganoderma lucidum and Cordyceps sinensis, it exhibits antimycobacterial, trypanocidal and antineoplastic activities.	2.06	1	0	3beta-sterol; ergostanoid; organic peroxide; phytosterols	antimycobacterial drug; antineoplastic agent; metabolite; trypanocidal drug
monomethyl fumarate monomethyl fumarate : A dicarboxylic acid monoester resulting from the formal condensation of one of the carboxy groups of fumaric acid with methanol. Is is a metabolite of dimethyl fumarate and used for the the treatment of patients with relapsing multiple sclerosis (MS). It also induces the NFE2L2 (Nrf2) transcription factor by binding to KEAP1.	2.05	1	0	dicarboxylic acid monoester; enoate ester; methyl ester	antioxidant; drug metabolite; immunomodulator
boron Boron: A trace element with the atomic symbol B, atomic number 5, and atomic weight [10.806; 10.821]. Boron-10, an isotope of boron, is used as a neutron absorber in BORON NEUTRON CAPTURE THERAPY.	2.11	1	0	boron group element atom; metalloid atom; nonmetal atom	micronutrient
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	2.47	2	0
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.	2.15	1	0
caftaric acid [no description available]	2.57	2	0	hydroxycinnamic acid
coniferyl ferulate coniferyl ferulate: found in the rhizome of Cnidium officinale Makino; structure given in first source; RN given refers to cpd without isomeric designation	2.13	1	0
isoacteoside isoacteoside: a phenylethanoid glycoside isolated from Indian paintbrush (Verbenaceae) Castilleja linariaefolia; also in other plants; structure given in first source	2.1	1	0	hydroxycinnamic acid
((3z)-n-(3-chlorophenyl)-3-((3,5-dimethyl-4-((4-methylpiperazin-1-yl)carbonyl)-1h-pyrrol-2-yl)methylene)-n-methyl-2-oxo-2,3-dihydro-1h-indole-5-sulfonamide) [no description available]	2.08	1	0	sulfonamide
chlorhexidine Chlorhexidine: A disinfectant and topical anti-infective agent used also as mouthwash to prevent oral plaque.. chlorhexidine : A bisbiguanide compound with a structure consisting of two (p-chlorophenyl)guanide units linked by a hexamethylene bridge.	2.15	1	0	biguanides; monochlorobenzenes	antibacterial agent; antiinfective agent
rosavin rosavin: isolated from Rhodiola rosea; structure in first source	4.08	4	0	O-acyl carbohydrate
sincalide Sincalide: An octapeptide hormone present in the intestine and brain. When secreted from the gastric mucosa, it stimulates the release of bile from the gallbladder and digestive enzymes from the pancreas.	1.99	1	0	oligopeptide
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).	2.15	1	0	aminopyrimidine; benzamides; pyridines; secondary amino compound; secondary carboxamide; substituted aniline	antineoplastic agent; apoptosis inducer; autophagy inducer; cardioprotective agent; EC 3.5.1.98 (histone deacetylase) inhibitor; hepatotoxic agent
cerebroside d cerebroside D: isolated from the fungus Lactarium volemus; structure in first source	2.06	1	0
cerevisterol cerevisterol: in mushroom family; Russian. cerevisterol : An ergostanoid that is (22E)-ergosta-7,22-diene substituted by hydroxy groups at positions 3, 5 and 6 (the 3beta,5alpha,6beta stereoisomer). It has been isolated from the fungus, Xylaria species.	2.06	1	0	3beta-hydroxy steroid; 5alpha-hydroxy steroid; 6beta-hydroxy steroid; ergostanoid	Aspergillus metabolite
alpha-synuclein alpha-Synuclein: A synuclein that is a major component of LEWY BODIES and plays a role in SYNUCLEINOPATHIES, neurodegeneration and neuroprotection.	2.21	1	0
rosarin rosarin: isolated from Rhodiola rosea; structure in first source	2.75	3	0	O-acyl carbohydrate
2-hydroxy-3-methylanthraquinone 2-hydroxy-3-methylanthraquinone: apoptosis-inducing compound from Hedyotis diffusa WILLD; structure in first source	2.1	1	0
ym 155 sepantronium bromide : An organic bromide salt consisting of sepantronium cations and bromide anions. It has been found to selectively inhibit survivin (BIRC5) gene promoter activity and to down-regulate survivin in vitro, so leading to induction of apoptosis.	3.51	1	0	organic bromide salt	antineoplastic agent; apoptosis inducer; survivin suppressant
procyanidin b1 procyanidin B1 : A proanthocyanidin consisting of (-)-epicatechin and (+)-catechin units joined by a bond between positions 4 and 8' respectively in a beta-configuration.. Procyanidin B1 can be found in Cinnamomum verum (Ceylon cinnamon, in the rind, bark or cortex), in Uncaria guianensis (cat's claw, in the root), and in Vitis vinifera (common grape vine, in the leaf) or in peach.	2.11	1	0	biflavonoid; hydroxyflavan; polyphenol; proanthocyanidin	anti-inflammatory agent; EC 3.4.21.5 (thrombin) inhibitor; metabolite
Dihydrotanshinone I dihydrotanshinone I: extracted from Radix Salviae	3.51	1	0	abietane diterpenoid	anticoronaviral agent
2,4,3',5'-tetrahydroxystilbene oleocanthal: newly pressed extra-virgin olive oil contains oleocanthal, acting as a natural anti-inflammatory compound that has a potency and profile strikingly similar to that of ibuprofen; structure in first source. oleocanthal : A carboxylic ester that is the 2-(p-hydroxyphenyl)ethyl ester of (3S)-4-formyl-3-(2-oxoethyl)hex-4-enoic acid. Oleocanthal is found in olive oil but it is not clear whether the natural product is a mixture of E/Z isomers or a single isomer as the two isomers readily interconvert in solution; most pharmacological studies will have been performed using a mixture.	4.52	6	0
scopolamine hydrobromide [no description available]	2.41	1	0
phytosterols Phytosterols: A class of organic compounds known as sterols or STEROIDS derived from plants.. phytosterols : Sterols similar to cholesterol which occur in plants and vary only in carbon side chains and/or presence or absence of a double bond.	2.06	1	0
alloin [no description available]	3.51	1	0	anthracenes; C-glycosyl compound; cyclic ketone; phenols	laxative; metabolite
ligstroside ligstroside: structure in first source. ligstroside : 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 4-hydroxyphenethyl ester (the 2S,3E,4S stereoisomer). An important phenolic compound present in olive cultivars.	3.87	3	0	beta-D-glucoside; diester; methyl ester; phenols; pyrans; secoiridoid glycoside	antineoplastic agent; plant metabolite
lasiodiplodin lasiodiplodin: structure in first source	2.03	1	0
cytochrome c-t Cytochromes c: Cytochromes of the c type that are found in eukaryotic MITOCHONDRIA. They serve as redox intermediates that accept electrons from MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX III and transfer them to MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX IV.	2.07	1	0
agrimoniin agrimoniin: tannin of Agrimonia pilosa; structure given in first source. agrimoniin : A dimeric hydrolysable tannin in which 2 moles of potentillin monomer are linked via a dehydrogalloyl group; an antitumor tannin of Agrimonia pilosa Ledeb., which induces interleukin-1.	2.03	1	0	tannin
cellulose DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.	2.25	1	0	glycoside
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	2.49	2	0	1,2-diacyl-sn-glycero-3-phosphocholine
chlorophyll a Chlorophyll: Porphyrin derivatives containing magnesium that act to convert light energy in photosynthetic organisms.. chlorophyll : A family of magnesium porphyrins, defined by the presence of a fifth ring beyond the four pyrrole-like rings. The rings can have various side chains which usually include a long phytol chain.	2.05	1	0	chlorophyll; methyl ester	cofactor
endiandrin a endiandrin A: a potent glucocorticoid receptor binder isolated from the Australian plant Endiandra anthropophagorum; structure in first source	2.46	2	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.	3.9	4	0
2,3,4,10-tetrahydro-7,10-dimethyl-2,4-dioxobenzo(g)pteridine [no description available]	3.51	1	0	flavin
3,4-dihydroxyphenylethanol-elenolic acid dialdehyde oleacein: found in olive oil; structure in first source	3.78	2	0	alcohol; phenols
chitosan [no description available]	3.04	3	0
tanshinone ii a sodium sulfonate tanshinone II A sodium sulfonate: has cardioprotective activity; water-soluble derivative of tanshinone II A; isolated from Salvia militiorrhiza; relieves anginal pain; structure	3.51	1	0
methyl jasmonate [no description available]	2.6	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.	2.13	1	0	organic cation; sulfonium compound	coenzyme; cofactor; human metabolite; micronutrient; Mycoplasma genitalium metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
ethyl cellulose [no description available]	2.25	1	0	glycoside
GRL-0617 GRL-0617 : A benzamide resulting from the formal condensation of the carboxy group of 5-amino-2-methylbenzoic acid with the amino group of (1R)-1-(naphthalen-1-yl)ethan-1-amine. It is a potent noncovalent inhibitor (IC50 = 600 nM) of severe acute respiratory syndrome-coronavirus papain-like protease (SARS-CoV PLpro).	3.51	1	0	benzamides; naphthalenes; secondary carboxamide; substituted aniline	anticoronaviral agent; protease inhibitor
N-trans-sinapoyltyramine [no description available]	2.13	1	0	hydroxycinnamic acid	metabolite
2-hydroxy-5-carboxymethylmuconate semialdehyde 2-hydroxy-5-carboxymethylmuconate semialdehyde: metabolite of 3,4-dihydroxyphenylacetate; structure. 5-formyl-2-hydroxyhepta-2,4-dienedioate : Dicarboxylate anion of 5-formyl-2-hydroxyhepta-2,4-dienedioic acid; major species at pH 7.3.	2.03	1	0
KOM70144 KOM70144 : A benzamide that is GRL-0617 in which one of the hydrogen's of the primary amino group is replaced by an acetyl group. It an inhibitor of SARS-CoV and SARS-CoV-2 papain-like protease (PLpro) with an IC50 of 2.6 muM and 5.0 muM, respectively. It also inhibits SARS-CoV and SARS-CoV-2 infection of Vero E6 cells in vitro (EC50 values are 13.1 and 21 muM, respectively).	3.51	1	0	acetamides; benzamides; naphthalenes; secondary carboxamide	anticoronaviral agent; protease inhibitor
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.	3.5	1	1
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.	2.15	1	0
isoquercitrin [no description available]	2	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.	2.15	1	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.	3.95	4	0	benzenes; hydroxycoumarin; methyl ketone
phytoestrogens Phytoestrogens: Compounds derived from plants, primarily ISOFLAVONES that mimic or modulate endogenous estrogens, usually by binding to ESTROGEN RECEPTORS.	3.19	1	0
oleuropein aglycone oleuropein aglycone: an agonist of both TRPA1 and TRPV1 receptors. oleuropein aglycone : A secoiridoid 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 carboxylic acid moiety of the carboxymethyl substituent has been converted to the corresponding 3,4-dihydroxyphenethyl ester (the 2R,3E,4S stereoisomer). The most important phenolic compound present in olive cultivars.	2.25	1	0	catechols; diester; lactol; methyl ester; pyrans; secoiridoid	anti-inflammatory agent; antioxidant; mTOR inhibitor; neuroprotective agent; plant metabolite; TRPA1 channel agonist
agar Agar: A complex sulfated polymer of galactose units, extracted from Gelidium cartilagineum, Gracilaria confervoides, and related red algae. It is used as a gel in the preparation of solid culture media for microorganisms, as a bulk laxative, in making emulsions, and as a supporting medium for immunodiffusion and immunoelectrophoresis.. agar : A complex mixture of polysaccharides extracted from species of red algae. Its two main components are agarose and agaropectin. Agarose is the component responsible for the high-strength gelling properties of agar, while agaropectin provides the viscous properties.	2.15	1	0
hydroxytyrosyl acetate hydroxytyrosyl acetate: structure in first source	2.54	2	0
t-2 toxin T-2 Toxin: A potent mycotoxin produced in feedstuffs by several species of the genus FUSARIUM. It elicits a severe inflammatory reaction in animals and has teratogenic effects.. T-2 toxin : A trichothecene mycotoxin produced by fungi of the genus Fusarium. It is a common contaminant in food and feedstuffs of cereal origin and is known to cause a range of toxic effects in humans and animals.	2.6	1	0
trichodermin Trichodermin: Antifungal metabolite from several fungi, mainly Trichoderma viride; inhibits protein synthesis by binding to ribosomes; proposed as antifungal and antineoplastic; used as tool in cellular biochemistry.. trichodermin : A tetracyclic spiroepoxide which acts as an antifungal and protein synthesis inhibitor.	2.47	2	0
amyloid beta-peptides amyloid beta-protein (1-40): although acutely neurotoxic in both rat & monkey cerebral cortex, neuronal degeneration in primates resembles more closely to that found in Alzheimer's disease; amino acid sequence has been determined	2.25	1	0
liriodendrin, 1r-(1alpha,3abeta,4beta,6aalpha)-isomer eleutheroside E: from Eleutherococcus senticosus extract	2.06	1	0
inosine [no description available]	2.03	1	0	inosines; purines D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
pheophytin a pheophytin a: structure given in first source; RN given refers to (3S-(3alpha(2E,7S,11S),4beta,21beta))-isomer	2.41	1	0
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.	1.99	1	0	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger
trypan blue Trypan Blue: A diazo-naphthalene sulfonate that is widely used as a stain.. trypan blue : An organosulfonate salt that is the tetrasodium salt of 3,3'-[(3,3'-dimethylbiphenyl-4,4'-diyl)didiazene-2,1-diyl]bis(5-amino-4-hydroxynaphthalene-2,7-disulfonic acid).	2.13	1	0
prodigiosin Prodigiosin: 4-Methoxy-5-((5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl)- 2,2'-bi-1H-pyrrole. A toxic, bright red tripyrrole pigment from Serratia marcescens and others. It has antibacterial, anticoccidial, antimalarial, and antifungal activities, but is used mainly as a biochemical tool.. prodigiosin : A member of the class of tripyrroles that is a red-coloured pigment with antibiotic properties produced by Serratia marcescens.	2.31	1	0
maltodextrin maltodextrin : A dextrin in which the D-glucose units are linked by alpha-(1->4) glycosidic bonds.	2.13	1	0

Condition	Relationship Strength	Studies	Trials
Innate Inflammatory Response [description not available]	4.52	8	0
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	4.52	8	0
Breast Cancer [description not available]	2.48	2	0
Metastase [description not available]	2.08	1	0
Breast Neoplasms Tumors or cancer of the human BREAST.	2.48	2	0
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	2.08	1	0
Injury, Ischemia-Reperfusion [description not available]	3.02	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.	3.02	4	0
Cirrhosis, Liver [description not available]	4.26	10	0
Liver Cirrhosis Liver disease in which the normal microcirculation, the gross vascular anatomy, and the hepatic architecture have been variably destroyed and altered with fibrous septa surrounding regenerated or regenerating parenchymal nodules.	4.26	10	0
Atherogenesis [description not available]	5.31	4	1
Atherosclerosis A thickening and loss of elasticity of the walls of ARTERIES that occurs with formation of ATHEROSCLEROTIC PLAQUES within the ARTERIAL INTIMA.	5.31	4	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).	2.41	1	0
Cardiac Remodeling, Ventricular [description not available]	2.41	1	0
Cardiovascular Stroke [description not available]	2.78	3	0
Myocardial Infarction NECROSIS of the MYOCARDIUM caused by an obstruction of the blood supply to the heart (CORONARY CIRCULATION).	2.78	3	0
Acute Confusional Senile Dementia [description not available]	4.06	4	0
Age-Related Memory Disorders [description not available]	2.41	1	0
Alzheimer Disease A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)	4.06	4	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.	2.41	1	0
E coli Infections [description not available]	3.52	4	0
Diarrhea An increased liquidity or decreased consistency of FECES, such as running stool. Fecal consistency is related to the ratio of water-holding capacity of insoluble solids to total water, rather than the amount of water present. Diarrhea is not hyperdefecation or increased fecal weight.	3.52	4	0
Escherichia coli Infections Infections with bacteria of the species ESCHERICHIA COLI.	3.52	4	0
Chronic Illness [description not available]	3.52	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).	3.52	1	0
Autosomal Dominant Juvenile Parkinson Disease [description not available]	2.21	1	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	3.96	12	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.	2.21	1	0
Parkinsonian Disorders A group of disorders which feature impaired motor control characterized by bradykinesia, MUSCLE RIGIDITY; TREMOR; and postural instability. Parkinsonian diseases are generally divided into primary parkinsonism (see PARKINSON DISEASE), secondary parkinsonism (see PARKINSON DISEASE, SECONDARY) and inherited forms. These conditions are associated with dysfunction of dopaminergic or closely related motor integration neuronal pathways in the BASAL GANGLIA.	2.21	1	0
Anterior Circulation Transient Ischemic Attack [description not available]	2.49	2	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)	2.49	2	0
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	3.42	2	0
Degenerative Diseases, Central Nervous System [description not available]	3.17	1	0
Neurodegenerative Diseases Hereditary and sporadic conditions which are characterized by progressive nervous system dysfunction. These disorders are often associated with atrophy of the affected central or peripheral nervous system structures.	3.17	1	0
Diabetes Mellitus, Adult-Onset [description not available]	3.71	3	0
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.	3.71	3	0
Extravascular Hemolysis [description not available]	2.25	1	0
Hemolysis The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.	2.25	1	0
Benign Neoplasms [description not available]	3.87	2	0
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.	3.87	2	0
Alloxan Diabetes [description not available]	3.08	4	0
Astrocytoma, Grade IV [description not available]	2.31	1	0
Glioblastoma A malignant form of astrocytoma histologically characterized by pleomorphism of cells, nuclear atypia, microhemorrhage, and necrosis. They may arise in any region of the central nervous system, with a predilection for the cerebral hemispheres, basal ganglia, and commissural pathways. Clinical presentation most frequently occurs in the fifth or sixth decade of life with focal neurologic signs or seizures.	2.31	1	0
Asthma, Bronchial [description not available]	2.31	1	0
Asthma A form of bronchial disorder with three distinct components: airway hyper-responsiveness (RESPIRATORY HYPERSENSITIVITY), airway INFLAMMATION, and intermittent AIRWAY OBSTRUCTION. It is characterized by spasmodic contraction of airway smooth muscle, WHEEZING, and dyspnea (DYSPNEA, PAROXYSMAL).	2.31	1	0
Anasarca [description not available]	2.15	1	0
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	2.15	1	0
Lung Injury, Acute [description not available]	2.55	2	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).	2.55	2	0
Brain Vascular Disorders [description not available]	2.17	1	0
Blood Pressure, High [description not available]	3.39	2	0
Cerebrovascular Disorders A spectrum of pathological conditions of impaired blood flow in the brain. They can involve vessels (ARTERIES or VEINS) in the CEREBRUM, the CEREBELLUM, and the BRAIN STEM. Major categories include INTRACRANIAL ARTERIOVENOUS MALFORMATIONS; BRAIN ISCHEMIA; CEREBRAL HEMORRHAGE; and others.	2.17	1	0
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.	3.39	2	0
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	3.14	5	0
Coronary Occlusion Complete blockage of blood flow through one of the CORONARY ARTERIES, usually from CORONARY ATHEROSCLEROSIS.	2.17	1	0
Arrhythmia [description not available]	3.67	3	0
Injury, Myocardial Reperfusion [description not available]	3.17	5	0
Heart Disease, Ischemic [description not available]	2.49	2	0
Arrhythmias, Cardiac Any disturbances of the normal rhythmic beating of the heart or MYOCARDIAL CONTRACTION. Cardiac arrhythmias can be classified by the abnormalities in HEART RATE, disorders of electrical impulse generation, or impulse conduction.	3.67	3	0
Ventricular Fibrillation A potentially lethal cardiac arrhythmia that is characterized by uncoordinated extremely rapid firing of electrical impulses (400-600/min) in HEART VENTRICLES. Such asynchronous ventricular quivering or fibrillation prevents any effective cardiac output and results in unconsciousness (SYNCOPE). It is one of the major electrocardiographic patterns seen with CARDIAC ARREST.	2.48	2	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).	2.49	2	0
Sterility, Male [description not available]	2.17	1	0
Hypospermatogenesis [description not available]	2.17	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.	2.17	1	0
Uveitis, Anterior Inflammation of the anterior uvea comprising the iris, angle structures, and the ciliary body. Manifestations of this disorder include ciliary injection, exudation into the anterior chamber, iris changes, and adhesions between the iris and lens (posterior synechiae). Intraocular pressure may be increased or reduced.	2.21	1	0
Colitis Gravis [description not available]	2.21	1	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.	2.21	1	0
Infections, Prosthesis-Related [description not available]	2.21	1	0
Cognitive Decline [description not available]	2.21	1	0
Cognitive Dysfunction Diminished or impaired mental and/or intellectual function.	2.21	1	0
Abnormalities, Autosome [description not available]	2.08	1	0
Idiopathic Parkinson Disease [description not available]	2.47	2	0
Parkinson Disease A progressive, degenerative neurologic disease characterized by a TREMOR that is maximal at rest, retropulsion (i.e. a tendency to fall backwards), rigidity, stooped posture, slowness of voluntary movements, and a masklike facial expression. Pathologic features include loss of melanin containing neurons in the substantia nigra and other pigmented nuclei of the brainstem. LEWY BODIES are present in the substantia nigra and locus coeruleus but may also be found in a related condition (LEWY BODY DISEASE, DIFFUSE) characterized by dementia in combination with varying degrees of parkinsonism. (Adams et al., Principles of Neurology, 6th ed, p1059, pp1067-75)	2.47	2	0
Dermatoses [description not available]	3.01	1	0
Skin Diseases Diseases involving the DERMIS or EPIDERMIS.	3.01	1	0
Endotoxemia A condition characterized by the presence of ENDOTOXINS in the blood. On lysis, the outer cell wall of gram-negative bacteria enters the systemic circulation and initiates a pathophysiologic cascade of pro-inflammatory mediators.	2.08	1	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	2.47	2	0
Hyperglycemia, Postprandial Abnormally high BLOOD GLUCOSE level after a meal.	2.11	1	0
Hyperglycemia Abnormally high BLOOD GLUCOSE level.	2.11	1	0
Chronic Kidney Diseases [description not available]	3.5	1	1
Renal Insufficiency, Chronic Conditions in which the KIDNEYS perform below the normal level for more than three months. Chronic kidney insufficiency is classified by five stages according to the decline in GLOMERULAR FILTRATION RATE and the degree of kidney damage (as measured by the level of PROTEINURIA). The most severe form is the end-stage renal disease (CHRONIC KIDNEY FAILURE). (Kidney Foundation: Kidney Disease Outcome Quality Initiative, 2002)	3.5	1	1
Acute Liver Injury, Drug-Induced [description not available]	2.74	3	0
Chemical and Drug Induced Liver Injury A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.	2.74	3	0
Allergic Reaction [description not available]	2.11	1	0
Hypersensitivity Altered reactivity to an antigen, which can result in pathologic reactions upon subsequent exposure to that particular antigen.	2.11	1	0
Caries, Dental [description not available]	2.13	1	0
Dental Caries Localized destruction of the tooth surface initiated by decalcification of the enamel followed by enzymatic lysis of organic structures and leading to cavity formation. If left unchecked, the cavity may penetrate the enamel and dentin and reach the pulp.	2.13	1	0
Cognition Disorders Disorders characterized by disturbances in mental processes related to learning, thinking, reasoning, and judgment.	3.04	1	0
Anterior Choroidal Artery Infarction [description not available]	2.47	2	0
Cerebral Ischemia [description not available]	2.13	1	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).	2.47	2	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.	2.13	1	0
Uveitis Inflammation of part or all of the uvea, the middle (vascular) tunic of the eye, and commonly involving the other tunics (sclera and cornea, and the retina). (Dorland, 27th ed)	2.53	2	0
Age-Related Osteoporosis [description not available]	2.44	2	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.	2.44	2	0
Cirrhosis [description not available]	2.04	1	0
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	2.04	1	0
Anoxemia [description not available]	2.05	1	0
Hypoxia Sub-optimal OXYGEN levels in the ambient air of living organisms.	2.05	1	0
Hyperlipemia [description not available]	2.06	1	0
Hyperlipidemias Conditions with excess LIPIDS in the blood.	2.06	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.	4.09	3	1
Fatigue, Mental [description not available]	2.93	1	0
Depression Depressive states usually of moderate intensity in contrast with MAJOR DEPRESSIVE DISORDER present in neurotic and psychotic disorders.	3.35	2	0
Biliary Cirrhosis [description not available]	2.03	1	0
Liver Cirrhosis, Biliary FIBROSIS of the hepatic parenchyma due to obstruction of BILE flow (CHOLESTASIS) in the intrahepatic or extrahepatic bile ducts (BILE DUCTS, INTRAHEPATIC; BILE DUCTS, EXTRAHEPATIC). Primary biliary cholangitis involves the destruction of small intra-hepatic bile ducts and decreased bile secretion. Secondary biliary cholangitis is produced by prolonged obstruction of large intrahepatic or extrahepatic bile ducts from a variety of causes.	2.03	1	0
Coronary Heart Disease [description not available]	2.03	1	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.	2.03	1	0
Cardiac Diseases [description not available]	9.64	9	9
Heart Diseases Pathological conditions involving the HEART including its structural and functional abnormalities.	9.64	9	9
Cerebral Infarction, Middle Cerebral Artery [description not available]	2.03	1	0
Dyskinesia Syndromes [description not available]	2.03	1	0
Sensation Disorders Disorders of the special senses (i.e., VISION; HEARING; TASTE; and SMELL) or somatosensory system (i.e., afferent components of the PERIPHERAL NERVOUS SYSTEM).	2.03	1	0
Movement Disorders Syndromes which feature DYSKINESIAS as a cardinal manifestation of the disease process. Included in this category are degenerative, hereditary, post-infectious, medication-induced, post-inflammatory, and post-traumatic conditions.	2.03	1	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.	2.03	1	0
Bone Loss, Perimenopausal [description not available]	2.03	1	0
Osteoporosis, Postmenopausal Metabolic disorder associated with fractures of the femoral neck, vertebrae, and distal forearm. It occurs commonly in women within 15-20 years after menopause, and is caused by factors associated with menopause including estrogen deficiency.	2.03	1	0
Celiac Sprue [description not available]	2.03	1	0
Celiac Disease A malabsorption syndrome that is precipitated by the ingestion of foods containing GLUTEN, such as wheat, rye, and barley. It is characterized by INFLAMMATION of the SMALL INTESTINE, loss of MICROVILLI structure, failed INTESTINAL ABSORPTION, and MALNUTRITION.	2.03	1	0
Adenocarcinoma, Basal Cell [description not available]	2.04	1	0
Cancer of Colon [description not available]	2.04	1	0
Invasiveness, Neoplasm [description not available]	2.04	1	0
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	2.04	1	0
Colonic Neoplasms Tumors or cancer of the COLON.	2.04	1	0
Malignant Melanoma [description not available]	2.04	1	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)	2.04	1	0
Atrioventricular Nodal Re-Entrant Tachycardia [description not available]	2.03	1	0
Tachycardia, Ventricular An abnormally rapid ventricular rhythm usually in excess of 150 beats per minute. It is generated within the ventricle below the BUNDLE OF HIS, either as autonomic impulse formation or reentrant impulse conduction. Depending on the etiology, onset of ventricular tachycardia can be paroxysmal (sudden) or nonparoxysmal, its wide QRS complexes can be uniform or polymorphic, and the ventricular beating may be independent of the atrial beating (AV dissociation).	2.03	1	0
Hepatocellular Carcinoma [description not available]	2.04	1	0
Liver Dysfunction [description not available]	2.04	1	0
Cancer of Liver [description not available]	2.04	1	0
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	2.04	1	0
Liver Diseases Pathological processes of the LIVER.	2.04	1	0
Liver Neoplasms Tumors or cancer of the LIVER.	2.04	1	0
B16 Melanoma [description not available]	2.04	1	0
Muscle Relaxation That phase of a muscle twitch during which a muscle returns to a resting position.	2	1	0

4-hydroxyphenylethanol

Description

Cross-References

Synonyms (98)

Research Excerpts

Toxicity

Pharmacokinetics

Bioavailability

Dosage Studied

Roles (7)

Drug Classes (1)

Pathways (3)

Protein Targets (11)

Potency Measurements

Inhibition Measurements

Other Measurements

Biological Processes (40)

Molecular Functions (23)

Ceullar Components (15)

Bioassays (80)

Research

Studies (451)

Market Indicators

Research Demand Index: 26.83

Study Types

Clinical Trials (2)

Trial Overview

4-hydroxyphenylethanol

Description

Cross-References

Synonyms (98)

Research Excerpts

Toxicity

Pharmacokinetics

Bioavailability

Dosage Studied

Roles (7)

Drug Classes (1)

Pathways (3)

Protein Targets (11)

Potency Measurements

Inhibition Measurements

Other Measurements

Biological Processes (40)

Molecular Functions (23)

Ceullar Components (15)

Bioassays (80)

Research

Studies (451)

Market Indicators

Research Demand Index: 26.83

Study Types

Clinical Trials (2)

Trial Overview

Related Drugs (339)

Related Conditions (136)