2-amino-3-methylimidazo(4,5-f)quinoline profile

2-amino-3-methylimidazo(4,5-f)quinoline, also known as IQ, is a heterocyclic amine that is a potent mutagen and carcinogen. It is found in cooked meats, especially those cooked at high temperatures. IQ is formed during the cooking process through the reaction of creatinine and sugars with amino acids. The compound is a potent mutagen in bacterial and mammalian cells, and it has been shown to cause tumors in rodents. IQ is of significant interest to researchers because of its potential contribution to human cancer risk. Studies are ongoing to investigate the mechanisms of its toxicity, including its metabolism, DNA adduct formation, and cellular signaling pathways. Understanding the biological activity of IQ is crucial for developing strategies to mitigate its carcinogenic effects, such as reducing exposure to cooked meat and promoting healthy cooking practices.'
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2-amino-3-methylimidazo(4,5-f)quinoline: mutagen found in broiled food; RN given refers to parent cpd; structure given in first source; frequently abbreviated as IQ in the literature [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

3-methyl-3H-imidazo[4,5-f]quinolin-2-amine : An imidazoquinoline that is 3H-imidazo[4,5-f]quinoline substituted by a methyl group at position 3 and an amino group at position 2. [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	53462
CHEMBL ID	1233049
CHEBI ID	42725
SCHEMBL ID	605923
MeSH ID	M0093320

Synonym
chebi:42725 ,
CHEMBL1233049
76180-96-6
2-amino-3-methylimidazo(4,5-f)-quinoline
3-methyl-3h-imidazo(4,5-f)quinolin-2-amine
2-amino-3-methylimidazo[4,5-f]quinoline
3h-imidazo(4,5-f)quinolin-2-amine, 3-methyl-
ccris 1767
hsdb 7085
2-amino-3-methyl-3h-imidazo(4,5-f)quinoline
n3-iq
brn 5014055
2-amino-3-methylimidazo(4,5-f)quinoline
3h-imidazo(4,5-f)quinoline, 2-amino-3-methyl-
2-amino-3-methylimidazo(4,5-f)- quinoline
2-amino-3-methylimidazo(4,5-f)quinoline hydrobromide
2-amino-3-methylimidazolo(4,5-f)quinoline
2-amiq
giq ,
3-methyl-3h-imidazo[4,5-f]quinolin-2-amine
iq
2-amino-3-methyl-3h-imidazo-[4,5-f]-quinoline
FT-0661919
FT-0661921
FT-0661920
3-methylimidazo[4,5-f]quinolin-2-amine
NCGC00248800-01
C19180
unii-30gl3d3t0g
30gl3d3t0g ,
dtxsid4020745 ,
cas-76180-96-6
NCGC00258247-01
tox21_200693
dtxcid00745
2-amino-3-methyl-3h-imidazo[4,5-f]quinoline
(3-methyl-3h-pyrido[3,2-e]benzoimidazol-2-yl)-amine
FT-0611062
SCHEMBL605923
2-amino-3-methylimidazo(4,5-f)quinoline [hsdb]
iq [iarc]
PS-3912
mfcd00210316
ARZWATDYIYAUTA-UHFFFAOYSA-N
AKOS026675474
2-amino-3-methyl-3h-imidazo[4 pound not5-f]quinoline
'2-amino-3-methylimidazo[4,5-f]quinoline'
3-methyl-3h-imidazo[4,5-f]quinolin-2-ylamine
Q27120486
2-amino-3-methyl-3h-imidazo[4,5-f]quinoline 10 microg/ml in acetonitrile
CS-0326450
PD061036
iq (iarc)

Excerpt	Reference	Relevance
" The reactive N-hydroxylamine metabolites N-hydroxy-IQ and N-hydroxy-PhIP are toxic to isolated rat cardiomyocytes."	( Protective effect of N-acetylcysteine against heterocyclic amine-induced cardiotoxicity in cultured myocytes and in rats. Davis, CD; Snyderwine, EG, 1995)	0.29
" The toxic effects of heterocyclic amines were also evaluated in rats given IQ or PhIP (100 mg/kg, po 10 doses over 2 weeks)."	( Cardiotoxicity of heterocyclic amine food mutagens in cultured myocytes and in rats. Davis, CD; Farb, A; Snyderwine, EG; Thorgeirsson, SS; Virmani, R, 1994)	0.29

Excerpt	Reference	Relevance
"025% 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) for two weeks combined with partial hepatectomy at the end of the first week and followed by long-term treatment with phenobarbital (PB) or 3'-methyl-4-dimethylaminoazobenzene (3'-Me-DAB) from week 3 to week 86 resulted in dose-dependent development of liver and thyroid neoplastic and preneoplastic lesions."	( Dose-dependent induction of liver and thyroid neoplastic lesions by short-term administration of 2-amino-3-methylimidazo[4,5-f]quinoline combined with partial hepatectomy followed by phenobarbital or low dose 3'-methyl-4-dimethylaminoazobenzene promotion. Asamoto, M; Inoue, T; Ito, N; Nagao, M; Ogiso, T; Tsuda, H, 1988)	0.27
"Mutagenic activity detected in beef extracts and in fried beef heated for varying periods of time was purified and then analysed by high-performance liquid chromatography in combination with mass spectrometry (LC-MS)."	( Analysis of mutagenic heterocyclic amines in cooked beef products by high-performance liquid chromatography in combination with mass spectrometry. Aeschbacher, HU; Bur, H; Huynh-Ba, T; Milon, H; Turesky, RJ, 1988)	0.27

Excerpt	Relevance	Reference
" One polar metabolite present in the urine, IQ-sulphamate (39%), was found at considerably higher levels in rats dosed orally with IQ compared with those fed IQ (less than 6%)."	( Metabolism of 2-amino-3-methylimidazo[4,5-f]quinoline in the male rat. Inamasu, T; Luks, H; Vavrek, MT; Weisburger, JH, 1989)	0.28
" Among the many blood proteins modified in rats dosed intragastrically with [3H(G)]IQ, hemoglobin and albumin were modified in a dose dependent fashion."	( Binding of 2-amino-3-methylimidazo[4,5-f]quinoline to hemoglobin and albumin in vivo in the rat. Identification of an adduct suitable for dosimetry. Skipper, PL; Tannenbaum, SR; Turesky, RJ, 1987)	0.27
" N-Acetylcysteine pretreatment also significantly reduced the percentage of cardiac cells with T-tubule dilation and myelin figures in adult rats dosed with IQ."	( Protective effect of N-acetylcysteine against heterocyclic amine-induced cardiotoxicity in cultured myocytes and in rats. Davis, CD; Snyderwine, EG, 1995)	0.29
" The finding of high cardiac IQ-DNA adduct levels prompted a histopathological study of perfusion-fixed hearts from 10 tumor-bearing monkeys chronically dosed with IQ at 10 mg/kg or 20 mg/kg 5 days per week for 48-80 months."	( Cardiac damage induced by 2-amino-3-methyl-imidazo[4,5-f]quinoline in nonhuman primates. Adamson, RH; Farb, A; Thorgeirsson, UP; Virmani, R, 1994)	0.29
" In an ongoing carcinogenesis study, 34 out of 40 monkeys dosed with IQ have developed malignant liver tumors."	( Liver tumors and possible preneoplastic lesions, induced by a food-derived heterocyclic amine in cynomolgus monkeys; a study of histology and cytokeratin expression. Adamson, RH; Gomez, DE; Lindsay, CK; Sinha, CC; Thorgeirsson, UP, 1996)	0.29
"This study describes histopathological findings in 26 nonhuman primates (cynomolgus and rhesus monkeys) with liver tumors after dosing with IQ for time periods of 27 to 72 months."	( Histopathology of IQ-induced hepatocarcinogenesis in nonhuman primates. Adamson, RH; Gomez, DE; Nagy, P; Sinha, CC; Thorgeirsson, UP, 1995)	0.29
" Notably MeIQx is poorly activated in cynomolgus monkeys and lacks the potency of IQ to induce hepatocellular carcinoma after a 5-year dosing period."	( Metabolism of food-derived heterocyclic amines in nonhuman primates. Adamson, RH; Davis, CD; Nagao, M; Sadrieh, N; Schut, HA; Snyderwine, EG; Sugimura, T; Thorgeirsson, SS; Thorgeirsson, UP; Turesky, RJ; Turteltaub, KW, 1997)	0.3
" The present study examined the dose-response for induction of CYP1A1 versus CYP1A2 by I3C, and compared the profiles of induction with the dose-response for inhibition of IQ-DNA adducts in the colon of the F344 rat."	( Inhibition of 2-amino-3-methylimidazo[4,5-f]quinoline-DNA adducts by indole-3-carbinol: dose-response studies in the rat colon. Bailey, GS; Bjeldanes, LF; Dashwood, RH; Schut, HA; Williams, DE; Xu, M, 1997)	0.3
" The 2 week IQ dosing protocol was used in a second experiment in which male F344 rats from Simonsen Laboratories (SN) or NCI were fed AIN-93G, AIN-76A or chow diet."	( Effect of carcinogen dose fractionation, diet and source of F344 rat on the induction of colonic aberrant crypts by 2-amino-3-methylimidazo[4,5-f]quinoline. Chen, R; Dashwood, RH; Xu, M, 1999)	0.3
" There were dose-response relationships of DNA adducts ((32)P-postlabeling) and DNA strand breaks (comet assay) in colon and liver tissues, with the highest levels of DNA adducts and strand breaks in the colon."	( Mutagenicity of 2-amino-3-methylimidazo[4,5-f]quinoline in colon and liver of Big Blue rats: role of DNA adducts, strand breaks, DNA repair and oxidative stress. Autrup, H; Daneshvar, B; Dragsted, LO; Hald, MT; Loft, S; Møller, P; Poulsen, HE; Risom, L; Vogel, U; Wallin, H, 2002)	0.31
" Three hours after dosing with PhIP, PhIP-DNA adduct levels were statistically significantly lower in KO mice than in WT mice in all tissues examined."	( Effect of CYP1A2 deficiency on heterocyclic amine DNA adduct levels in mice. Kimura, S; Knight-Jones, L; Schut, HA; Snyderwine, EG; Yu, M, 2002)	0.31
" In animals not dosed with IQ, sucrose increased the adduct level in both organs but to a lower level than IQ."	( Effects of sucrose and cornstarch on 2-amino-3-methylimidazo[4,5-f]quinoline (IQ)-induced colon and liver carcinogenesis in F344 rats. Autrup, H; Dragsted, LO; Lindecrona, RH; Mølck, AM; Poulsen, M; Vogel, U, 2004)	0.32
" We especially looked for any deviation from linearity of the dose-response curves."	( A comparison of genotoxicity between three common heterocyclic amines and acrylamide. Abramsson-Zetterberg, L; Durling, LJ, 2005)	0.33
"01, respectively) in mice belonging to all EGCG dosing groups."	( Protective effects of epigallocatechin gallate on colon preneoplastic lesions induced by 2-amino-3-methylimidazo[4,5-f ] quinoline in mice. Li, YQ; Yang, XY; Yuan, JH, )	0.13
" This result indicates the importance of dosage when interpreting data on the carcinogenicity and metabolic activation of IQ."	( Low-dose carcinogenicity of 2-amino-3-methylimidazo[4,5-f ]quinoline in rats: Evidence for the existence of no-effect levels and a mechanism involving p21(Cip / WAF1). Fukushima, S; Hirose, M; Nakae, D; Takahashi, S; Tatematsu, M; Totsuka, Y; Tsuda, H; Wanibuchi, H; Wei, M, 2011)	0.37
" The selected dosage was 5 mg/kg for both heterocyclic amines."	( Impact of aqueous doash extract on urinary mutagenicity in rats exposed to heterocyclic amines. Ioanndes, C; Jalal, JA; Khan, JA; Moselhy, SS, 2013)	0.39

Role	Description
carcinogenic agent	A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.
[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
imidazoquinoline
[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]

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Luciferase	Photinus pyralis (common eastern firefly)	Potency	67.4626	0.0072	15.7588	89.3584	AID1224835
acetylcholinesterase	Homo sapiens (human)	Potency	45.1302	0.0025	41.7960	15,848.9004	AID1347395; AID1347398
RAR-related orphan receptor gamma	Mus musculus (house mouse)	Potency	25.7283	0.0060	38.0041	19,952.5996	AID1159521; AID1159523
GLI family zinc finger 3	Homo sapiens (human)	Potency	20.6137	0.0007	14.5928	83.7951	AID1259369
AR protein	Homo sapiens (human)	Potency	7.8763	0.0002	21.2231	8,912.5098	AID1259247; AID743054
nuclear receptor subfamily 1, group I, member 3	Homo sapiens (human)	Potency	30.7691	0.0010	22.6508	76.6163	AID1224838; AID1224839; AID1224893
retinoic acid nuclear receptor alpha variant 1	Homo sapiens (human)	Potency	43.1989	0.0030	41.6115	22,387.1992	AID1159552; AID1159553; AID1159555
estrogen-related nuclear receptor alpha	Homo sapiens (human)	Potency	20.6137	0.0015	30.6073	15,848.9004	AID1259401
pregnane X nuclear receptor	Homo sapiens (human)	Potency	51.7792	0.0054	28.0263	1,258.9301	AID1346982
aryl hydrocarbon receptor	Homo sapiens (human)	Potency	6.5712	0.0007	23.0674	1,258.9301	AID743085; AID743122
cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_a	Homo sapiens (human)	Potency	14.5934	0.0017	23.8393	78.1014	AID743083
thyroid stimulating hormone receptor	Homo sapiens (human)	Potency	51.7792	0.0016	28.0151	77.1139	AID1259385
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	109 (23.54)	18.7374
1990's	219 (47.30)	18.2507
2000's	105 (22.68)	29.6817
2010's	27 (5.83)	24.3611
2020's	3 (0.65)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	15 (3.13%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	465 (96.88%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	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.	2.31	1	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
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.	2.02	1	monocarboxylic acid	antibacterial agent; astringent; metabolite; protic solvent; solvent
chlorine chloride : A halide anion formed when chlorine picks up an electron to form an an anion.	1.97	1	halide anion; monoatomic chlorine	cofactor; Escherichia coli metabolite; human metabolite
coumarin 2H-chromen-2-one: coumarin derivative	1.99	1	coumarins	fluorescent dye; human metabolite; plant metabolite
creatine [no description available]	3.99	4	glycine derivative; guanidines; zwitterion	geroprotector; human metabolite; mouse metabolite; neuroprotective agent; nutraceutical
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	1	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
glycine [no description available]	2.38	2	alpha-amino acid; amino acid zwitterion; proteinogenic amino acid; serine family amino acid	EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor; fundamental metabolite; hepatoprotective agent; micronutrient; neurotransmitter; NMDA receptor agonist; nutraceutical
pyruvaldehyde Pyruvaldehyde: An organic compound used often as a reagent in organic synthesis, as a flavoring agent, and in tanning. It has been demonstrated as an intermediate in the metabolism of acetone and its derivatives in isolated cell preparations, in various culture media, and in vivo in certain animals.. methylglyoxal : A 2-oxo aldehyde derived from propanal.	1.98	1	2-oxo aldehyde; propanals	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
methanol Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.	2.4	2	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
niacinamide nicotinamide : A pyridinecarboxamide that is pyridine in which the hydrogen at position 3 is replaced by a carboxamide group.	1.97	1	pyridine alkaloid; pyridinecarboxamide; vitamin B3	anti-inflammatory agent; antioxidant; cofactor; EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; Escherichia coli metabolite; geroprotector; human urinary metabolite; metabolite; mouse metabolite; neuroprotective agent; Saccharomyces cerevisiae metabolite; Sir2 inhibitor
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	2.01	1	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)	2.37	2	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species	human metabolite
1-octanol 1-Octanol: A colorless, slightly viscous liquid used as a defoaming or wetting agent. It is also used as a solvent for protective coatings, waxes, and oils, and as a raw material for plasticizers. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). octan-1-ol : An octanol carrying the hydroxy group at position 1.	1.98	1	octanol; primary alcohol	antifungal agent; bacterial metabolite; fuel additive; kairomone; plant metabolite
4-nitrophenol 4-nitrophenol: RN given refers to parent cpd. mononitrophenol : A nitrophenol that is phenol carrying a single nitro substituent at unspecified position.. 4-nitrophenol : A member of the class of 4-nitrophenols that is phenol in which the hydrogen that is para to the hydroxy group has been replaced by a nitro group.	2.07	1	4-nitrophenols	human xenobiotic metabolite; mouse metabolite
pentachlorophenol PENTA: structure given in first source	1.96	1	aromatic fungicide; chlorophenol; organochlorine pesticide; pentachlorobenzenes	human xenobiotic metabolite
tryptamine [no description available]	2.66	3	aminoalkylindole; aralkylamino compound; indole alkaloid; tryptamines	human metabolite; mouse metabolite; plant 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).	1.99	1	benzaldehydes; monomethoxybenzene; phenols	anti-inflammatory agent; anticonvulsant; antioxidant; flavouring agent; plant metabolite
1,2-dimethylhydrazine 1,2-Dimethylhydrazine: A DNA alkylating agent that has been shown to be a potent carcinogen and is widely used to induce colon tumors in experimental animals.. 1,2-dimethylhydrazine : A member of the class of hydrazines that is hydrazine in which one of the hydrogens attached to each nitrogen is replaced by a methyl group. A powerful DNA alkylating agent and carcinogen, it is used to induce colon cancer in laboratory rats and mice.	2.93	4	hydrazines	alkylating agent; carcinogenic agent
2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine: mutagen from fried ground beef; structure given in first source. PhIP : An imidazopyridine that is 1H--imidazo[4,5-b]pyridine which is substituted at positions 1, 2, and 6 by methyl, amino, and phenyl groups, respectively. It is the most abundant of the mutagenic heterocyclic amines found in cooked meat and fish.	8.32	92	imidazopyridine; primary amino compound	carcinogenic agent; mutagen
2-aminofluorene [no description available]	3.07	5
3-methylcholanthrene Methylcholanthrene: A carcinogen that is often used in experimental cancer studies.. 3-methylcholanthrene : A pentacyclic ortho- and peri-fused polycyclic arene consisting of a dihydrocyclopenta[ij]tetraphene ring system with a methyl substituent at the 3-position.	2.89	4	ortho- and peri-fused polycyclic arene	aryl hydrocarbon receptor agonist; carcinogenic agent
5,5-dimethyl-1-pyrroline-1-oxide 5,5-dimethyl-1-pyrroline-1-oxide: do not confuse with DMPO (4',5'-dihydroxy-7-methoxy-4-phenyl-5,2'-oxidocoumarin). 5,5-dimethyl-1-pyrroline N-oxide : A member of the class of 1-pyrroline nitrones (1-pyrroline N-oxides) resulting from the formal N-oxidation of 5,5-dimethyl-1-pyrroline. Used as a spin trap for the study of radicals formed by enzymatic acetaldehyde oxidation.	3.49	2	1-pyrroline nitrones	neuroprotective agent; spin trapping reagent
5,8,11,14-eicosatetraynoic acid 5,8,11,14-Eicosatetraynoic Acid: A 20-carbon unsaturated fatty acid containing 4 alkyne bonds. It inhibits the enzymatic conversion of arachidonic acid to prostaglandins E(2) and F(2a).	1.99	1	long-chain fatty acid
theophylline [no description available]	2.05	1	dimethylxanthine	adenosine receptor antagonist; anti-asthmatic drug; anti-inflammatory agent; bronchodilator agent; drug metabolite; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; fungal metabolite; human blood serum metabolite; immunomodulator; muscle relaxant; vasodilator agent
antipyrine Antipyrine: An analgesic and antipyretic that has been given by mouth and as ear drops. Antipyrine is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver. (From Martindale, The Extra Pharmacopoeia, 30th ed, p29). antipyrine : A pyrazolone derivative that is 1,2-dihydropyrazol-3-one substituted with methyl groups at N-1 and C-5 and with a phenyl group at N-2.	3.17	1	pyrazolone	antipyretic; cyclooxygenase 3 inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
aspirin Aspirin: The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5). acetylsalicylate : A benzoate that is the conjugate base of acetylsalicylic acid, arising from deprotonation of the carboxy group.. acetylsalicylic acid : A member of the class of benzoic acids that is salicylic acid in which the hydrogen that is attached to the phenolic hydroxy group has been replaced by an acetoxy group. A non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity.	1.98	1	benzoic acids; phenyl acetates; salicylates	anticoagulant; antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; EC 1.1.1.188 (prostaglandin-F synthase) inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; plant activator; platelet aggregation inhibitor; prostaglandin antagonist; teratogenic agent
benzo(a)pyrene Benzo(a)pyrene: A potent mutagen and carcinogen. It is a public health concern because of its possible effects on industrial workers, as an environmental pollutant, an as a component of tobacco smoke.. benzo[a]pyrene : An ortho- and peri-fused polycyclic arene consisting of five fused benzene rings.	4.35	20	ortho- and peri-fused polycyclic arene	carcinogenic agent; mouse metabolite
beta-naphthoflavone beta-Naphthoflavone: A polyaromatic hydrocarbon inducer of P4501A1 and P4501A2 cytochromes. (Proc Soc Exp Biol Med 1994 Dec:207(3):302-308). beta-naphthoflavone : An extended flavonoid resulting from the formal fusion of a benzene ring with the f side of flavone.	3.38	7	extended flavonoid; naphtho-gamma-pyrone; organic heterotricyclic compound	aryl hydrocarbon receptor agonist
caffeine [no description available]	2.69	3	purine alkaloid; trimethylxanthine	adenosine A2A receptor antagonist; adenosine receptor antagonist; adjuvant; central nervous system stimulant; diuretic; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; environmental contaminant; food additive; fungal metabolite; geroprotector; human blood serum metabolite; mouse metabolite; mutagen; plant metabolite; psychotropic drug; ryanodine receptor agonist; xenobiotic
cetyltrimethylammonium ion Cetrimonium: Cetyltrimethylammonium compound whose salts and derivatives are used primarily as topical antiseptics.. cetyltrimethylammonium ion : A quaternary ammonium ion in which the substituents on nitrogen are one hexadecyl and three methyl groups.	1.99	1	quaternary ammonium ion
clofibrate angiokapsul: contains clofibrate & insoitolnicotinate	1.99	1	aromatic ether; ethyl ester; monochlorobenzenes	anticholesteremic drug; antilipemic drug; geroprotector; PPARalpha agonist
deferoxamine Deferoxamine: Natural product isolated from Streptomyces pilosus. It forms iron complexes and is used as a chelating agent, particularly in the mesylate form.. desferrioxamine B : An acyclic desferrioxamine that is butanedioic acid in which one of the carboxy groups undergoes formal condensation with the primary amino group of N-(5-aminopentyl)-N-hydroxyacetamide and the second carboxy group undergoes formal condensation with the hydroxyamino group of N(1)-(5-aminopentyl)-N(1)-hydroxy-N(4)-[5-(hydroxyamino)pentyl]butanediamide. It is a siderophore native to Streptomyces pilosus biosynthesised by the DesABCD enzyme cluster as a high affinity Fe(III) chelator.	1.96	1	acyclic desferrioxamine	bacterial metabolite; ferroptosis inhibitor; iron chelator; siderophore
ellipticine ellipticine : A organic heterotetracyclic compound that is pyrido[4,3-b]carbazole carrying two methyl substituents at positions 5 and 11.	2.4	2	indole alkaloid; organic heterotetracyclic compound; organonitrogen heterocyclic compound; polycyclic heteroarene	antineoplastic agent; plant metabolite
emodin Emodin: Purgative anthraquinone found in several plants, especially RHAMNUS PURSHIANA. It was formerly used as a laxative, but is now used mainly as a tool in toxicity studies.. emodin : A trihydroxyanthraquinone that is 9,10-anthraquinone which is substituted by hydroxy groups at positions 1, 3, and 8 and by a methyl group at position 6. It is present in the roots and barks of numerous plants (particularly rhubarb and buckthorn), moulds, and lichens. It is an active ingredient of various Chinese herbs.	1.97	1	trihydroxyanthraquinone	antineoplastic agent; laxative; plant metabolite; tyrosine kinase inhibitor
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.	2.04	1	ether; volatile organic compound	inhalation anaesthetic; non-polar solvent; refrigerant
ethoxyresorufin ethoxyresorufin: structure	1.98	1	phenoxazine
furafylline [no description available]	2.05	1	oxopurine
hydroxyurea [no description available]	1.96	1	one-carbon compound; ureas	antimetabolite; antimitotic; antineoplastic agent; DNA synthesis inhibitor; EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor; genotoxin; immunomodulator; radical scavenger; teratogenic agent
indole-3-carbinol indole-3-carbinol: occurs in edible cruciferous vegetables. indole-3-methanol : An indolyl alcohol carrying a hydroxymethyl group at position 3. It is a constituent of the cruciferous vegetables and had anticancer activity.	3.5	8	indolyl alcohol	antineoplastic agent; plant metabolite
indomethacin Indomethacin: A non-steroidal anti-inflammatory agent (NSAID) that inhibits CYCLOOXYGENASE, which is necessary for the formation of PROSTAGLANDINS and other AUTACOIDS. It also inhibits the motility of POLYMORPHONUCLEAR LEUKOCYTES.. indometacin : A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by p-chlorobenzoyl, methyl, and methoxy groups, respectively. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis.	1.99	1	aromatic ether; indole-3-acetic acids; monochlorobenzenes; N-acylindole	analgesic; drug metabolite; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; gout suppressant; non-steroidal anti-inflammatory drug; xenobiotic metabolite; xenobiotic
mesalamine Mesalamine: An anti-inflammatory agent, structurally related to the SALICYLATES, which is active in INFLAMMATORY BOWEL DISEASE. It is considered to be the active moiety of SULPHASALAZINE. (From Martindale, The Extra Pharmacopoeia, 30th ed). mesalamine : A monohydroxybenzoic acid that is salicylic acid substituted by an amino group at the 5-position.	3.18	1	amino acid; aromatic amine; monocarboxylic acid; monohydroxybenzoic acid; phenols	non-steroidal anti-inflammatory drug
methapyrilene Methapyrilene: Histamine H1 antagonist with sedative action used as a hypnotic and in allergies.. methapyrilene : A member of the class of ethylenediamine derivatives that is ethylenediamine in which one of the nitrogens is substituted by two methyl groups, and the other nitrogen is substituted by a 2-pyridyl group and a (2-thienyl)methyl group.	1.97	1	ethylenediamine derivative	anti-allergic agent; carcinogenic agent; H1-receptor antagonist; sedative
metyrapone Metyrapone: An inhibitor of the enzyme STEROID 11-BETA-MONOOXYGENASE. It is used as a test of the feedback hypothalamic-pituitary mechanism in the diagnosis of CUSHING SYNDROME.. metyrapone : An aromatic ketone that is 3,3-dimethylbutan-2-one in which the methyl groups at positions 1 and 4 are replaced by pyridin-3-yl groups. A steroid 11beta-monooxygenase (EC 1.14.15.4) inhibitor, it is used in the diagnosis of adrenal insufficiency.	2.37	2	aromatic ketone	antimetabolite; diagnostic agent; EC 1.14.15.4 (steroid 11beta-monooxygenase) inhibitor
phenobarbital Phenobarbital: A barbituric acid derivative that acts as a nonselective central nervous system depressant. It potentiates GAMMA-AMINOBUTYRIC ACID action on GABA-A RECEPTORS, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations.. phenobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and phenyl groups.	3.48	8	barbiturates	anticonvulsant; drug allergen; excitatory amino acid antagonist; sedative
sulforaphane sulforaphane: from Cardaria draba L.. sulforaphane : An isothiocyanate having a 4-(methylsulfinyl)butyl group attached to the nitrogen.	2.42	2	isothiocyanate; sulfoxide	antineoplastic agent; antioxidant; EC 3.5.1.98 (histone deacetylase) inhibitor; plant metabolite
tyramine [no description available]	2.38	2	monoamine molecular messenger; primary amino compound; tyramines	EC 3.1.1.8 (cholinesterase) inhibitor; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter
urethane [no description available]	3.07	1	carbamate ester	fungal metabolite; mutagen
mitomycin Mitomycin: An antineoplastic antibiotic produced by Streptomyces caespitosus. It is one of the bi- or tri-functional ALKYLATING AGENTS causing cross-linking of DNA and inhibition of DNA synthesis.. mitomycin : A family of aziridine-containing natural products isolated from Streptomyces caespitosus or Streptomyces lavendulae.	2.68	3	mitomycin	alkylating agent; antineoplastic agent
1,2,5,6-dibenzanthracene 1,2,5,6-dibenzanthracene: RN given refers to parent cpd	1.98	1	ortho-fused polycyclic arene	mutagen
n-hydroxy-2-aminofluorene N-hydroxy-2-aminofluorene: structure	1.98	1
2-acetylaminofluorene 2-Acetylaminofluorene: A hepatic carcinogen whose mechanism of activation involves N-hydroxylation to the aryl hydroxamic acid followed by enzymatic sulfonation to sulfoxyfluorenylacetamide. It is used to study the carcinogenicity and mutagenicity of aromatic amines.	3.48	8	2-acetamidofluorenes	antimitotic; carcinogenic agent; epitope; mutagen
diethylnitrosamine Diethylnitrosamine: A nitrosamine derivative with alkylating, carcinogenic, and mutagenic properties.. N-nitrosodiethylamine : A nitrosamine that is N-ethylethanamine substituted by a nitroso group at the N-atom.	3.25	6	nitrosamine	carcinogenic agent; hepatotoxic agent; mutagen
methyldimethylaminoazobenzene Methyldimethylaminoazobenzene: A very potent liver carcinogen.. 3-methyl-4'-dimethylaminoazobenzene : A member of the class of azobenzenes that is azobenzene in which one of the phenyl groups is substituted at position 3 by a methyl group, while the other is substituted at position 4 by a dimethylamino group. It is a potent liver carcinogen.	1.97	1
4-nitroquinoline-1-oxide 4-nitroquinoline N-oxide : A quinoline N-oxide carrying a nitro substituent at position 4.	3.26	6	C-nitro compound; quinoline N-oxide	carcinogenic agent
lysine Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.	1.98	1	aspartate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; lysine; organic molecular entity; proteinogenic amino acid	algal metabolite; anticonvulsant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
sulfamic acid sulfamic acid: standard in alkalimetry; RN given refers to parent cpd; structure. sulfamic acid : The simplest of the sulfamic acids consisting of a single sulfur atom covalently bound by single bonds to hydroxy and amino groups and by double bonds to two oxygen atoms.	2.68	3	sulfamic acids
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	3	glycosyl glycoside	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; sweetening agent
9,10-dimethyl-1,2-benzanthracene 9,10-Dimethyl-1,2-benzanthracene: Polycyclic aromatic hydrocarbon found in tobacco smoke that is a potent carcinogen.. 7,12-dimethyltetraphene : A tetraphene having methyl substituents at the 7- and 12-positions. It is a potent carcinogen and is present in tobacco smoke.	2.4	2	ortho-fused polycyclic arene; tetraphenes	carcinogenic agent
bromodeoxyuridine Bromodeoxyuridine: A nucleoside that substitutes for thymidine in DNA and thus acts as an antimetabolite. It causes breaks in chromosomes and has been proposed as an antiviral and antineoplastic agent. It has been given orphan drug status for use in the treatment of primary brain tumors.	2.7	3	pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent
carbostyril Quinolones: A group of derivatives of naphthyridine carboxylic acid, quinoline carboxylic acid, or NALIDIXIC ACID.. quinolin-2(1H)-one : A quinolone that is 1,2-dihydroquinoline substituted by an oxo group at position 2.	4.01	4	monohydroxyquinoline; quinolone	bacterial xenobiotic metabolite
ethyl methanesulfonate Ethyl Methanesulfonate: An antineoplastic agent with alkylating properties. It also acts as a mutagen by damaging DNA and is used experimentally for that effect.. ethyl methanesulfonate : A methanesulfonate ester resulting from the formal condensation of methanesulfonic acid with ethanol.	2.01	1	methanesulfonate ester	alkylating agent; antineoplastic agent; carcinogenic agent; genotoxin; mutagen; teratogenic agent
aniline [no description available]	2.1	1	anilines; primary arylamine
dimethylnitrosamine Dimethylnitrosamine: A nitrosamine derivative with alkylating, carcinogenic, and mutagenic properties. It causes serious liver damage and is a hepatocarcinogen in rodents.	2.94	4	nitrosamine	geroprotector; mutagen
androstenedione Androstenedione: A delta-4 C19 steroid that is produced not only in the TESTIS, but also in the OVARY and the ADRENAL CORTEX. Depending on the tissue type, androstenedione can serve as a precursor to TESTOSTERONE as well as ESTRONE and ESTRADIOL.. androst-4-ene-3,17-dione : A 3-oxo Delta(4)-steroid that is androst-4-ene substituted by oxo groups at positions 3 and 17. It is a steroid hormone synthesized in the adrenal glands and gonads.	1.97	1	17-oxo steroid; 3-oxo-Delta(4) steroid; androstanoid	androgen; Daphnia magna metabolite; human metabolite; mouse metabolite
histidine Histidine: An essential amino acid that is required for the production of HISTAMINE.. L-histidine : The L-enantiomer of the amino acid histidine.. histidine : An alpha-amino acid that is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3.	1.97	1	amino acid zwitterion; histidine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
threonine Threonine: An essential amino acid occurring naturally in the L-form, which is the active form. It is found in eggs, milk, gelatin, and other proteins.. threonine : An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 1-hydroxyethyl group.	2.41	2	amino acid zwitterion; aspartate family amino acid; L-alpha-amino acid; proteinogenic amino acid; threonine	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
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.	2.89	4	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
arginine Arginine: An essential amino acid that is physiologically active in the L-form.. arginine : An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group.	1.98	1	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
acetonitrile acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.	2.02	1	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
tert-butylhydroperoxide tert-Butylhydroperoxide: A direct-acting oxidative stress-inducing agent used to examine the effects of oxidant stress on Ca(2+)-dependent signal transduction in vascular endothelial cells. It is also used as a catalyst in polymerization reactions and to introduce peroxy groups into organic molecules.. tert-butyl hydroperoxide : An alkyl hydroperoxide in which the alkyl group is tert-butyl. It is widely used in a variety of oxidation processes.	2.73	3	alkyl hydroperoxide	antibacterial agent; oxidising agent
trichloroacetic acid Trichloroacetic Acid: A strong acid used as a protein precipitant in clinical chemistry and also as a caustic for removing warts.. trichloroacetic acid : A monocarboxylic acid that is acetic acid in which all three methyl hydrogens are substituted by chlorine.	1.99	1	monocarboxylic acid; organochlorine compound	carcinogenic agent; metabolite; mouse metabolite
acrylamide [no description available]	2.02	1	acrylamides; N-acylammonia; primary carboxamide	alkylating agent; carcinogenic agent; Maillard reaction product; mutagen; neurotoxin
1,4-dihydroxyanthraquinone 1,4-dihydroxyanthraquinone: structure given in first source. quinizarin : A dihydroxyanthraquinone having the two hydroxy substituents at the 1- and 4-positions; formally derived from anthraquinone by replacement of two hydrogen atoms by hydroxy groups	1.98	1	dihydroxyanthraquinone	dye
2,6-dihydroxyanthraquinone 2,6-dihydroxyanthraquinone: structure given in first source. anthraflavic acid : A dihydroxyanthraquinone that is anthracene substituted by hydroxy groups at C-3 and C-7 and oxo groups at C-9 and C-10.	3.08	1	dihydroxyanthraquinone	antimutagen; plant metabolite
2-aminodiphenyl aminobiphenyl : Any member of the class of biphenyls in which the biphenyl skeleton is substituted by at least one amino group.	1.96	1
quinoxalines quinoxaline : A naphthyridine in which the nitrogens are at positions 1 and 4.	7.39	88	mancude organic heterobicyclic parent; naphthyridine; ortho-fused heteroarene
4-biphenylamine 4-biphenylamine: used in detection of sulfates, & as a carcinogen in cancer research; RN given refers to parent cpd; structure. biphenyl-4-amine : An aminobiphenyl that is biphenyl substituted by an amino group at position 4.	2.69	3	aminobiphenyl	carcinogenic agent
trehalose alpha,alpha-trehalose : A trehalose in which both glucose residues have alpha-configuration at the anomeric carbon.	2.05	1	trehalose	Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
1,2-dichloro-4-nitrobenzene [no description available]	2.02	1
n-nitrosopiperidine N-nitrosopiperidine: structure. N-nitrosopiperidine : A nitrosamine that is piperidine in which the hydrogen attached to the nitrogen is replaced by a nitroso group. One of the many carcinogens detected in cigarette smoke, it is found in meat, cheese and spices that have been treated with the preservative sodium nitrite.	1.99	1	nitrosamine; piperidine	apoptosis inducer; carcinogenic agent; environmental contaminant; mutagen
acrolein [no description available]	1.99	1	enal	herbicide; human xenobiotic metabolite; toxin
3-methylpyridine 3-methylpyridine : A methylpyridine that is pyridine substituted by a methyl group at position 3.	1.98	1	methylpyridine
thiophenes Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.	1.98	1	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
diethylhexyl phthalate Diethylhexyl Phthalate: An ester of phthalic acid. It appears as a light-colored, odorless liquid and is used as a plasticizer for many resins and elastomers.. bis(2-ethylhexyl) phthalate : A phthalate ester that is the bis(2-ethylhexyl) ester of benzene-1,2-dicarboxylic acid.	2.02	1	diester; phthalate ester	androstane receptor agonist; apoptosis inhibitor; plasticiser
anthracene acene : A polycyclic aromatic hydrocarbon consisting of fused benzene rings in a rectilinear arrangement.. acenes : Polycyclic aromatic hydrocarbons consisting of fused benzene rings in a rectilinear arrangement and their substitution derivatives.	1.98	1	acene; anthracenes; ortho-fused tricyclic hydrocarbon
1-hydroxyanthraquinone [no description available]	1.98	1	monohydroxyanthraquinone
captan Captan: One of the phthalimide fungicides.. captan : A dicarboximide that is 3a,4,7,7a-tetrahydrophthalimide in which the hydrogen attached to the nitrogen is replaced by a trichloromethyl group. A non-systemic fungicide introduced in the 1950s, it is widely used for the control of fungal diseases in fruits, vegetables, and ornamental crops.	1.98	1	isoindoles; organochlorine compound; organosulfur compound; phthalimide fungicide	antifungal agrochemical
ethyl acetate ethyl acetate : The acetate ester formed between acetic acid and ethanol.	2	1	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.	3.25	6	catechin	antioxidant; plant metabolite
benzo(b)fluoranthene benzo[b]fluoranthene : An ortho- and peri-fused polycyclic arene that consists of a benzene ring fused with a acephenanthrylene ring.	1.98	1	ortho- and peri-fused polycyclic arene	mutagen
acridines Acridines: Compounds that include the structure of acridine.. acridine : A polycyclic heteroarene that is anthracene in which one of the central CH groups is replaced by a nitrogen atom.	2.05	1	acridines; mancude organic heterotricyclic parent; polycyclic heteroarene	genotoxin
indazoles Indazoles: A group of heterocyclic aromatic organic compounds consisting of the fusion of BENZENE and PYRAZOLES.	1.96	1	indazole
pyrazines Pyrazines: A heterocyclic aromatic organic compound with the chemical formula C4H4N2.. pyrazine : A diazine that is benzene in which the carbon atoms at positions 1 and 4 have been replaced by nitrogen atoms.	2.39	2	diazine; pyrazines	Daphnia magna metabolite
flavanone flavanone: RN given refers to cpd with unspecified isomeric designation; structure in first source. flavanone : The simplest member of the class of flavanones that consists of flavan bearing an oxo substituent at position 4.	1.98	1	flavanones
alpha-aminopyridine alpha-aminopyridine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #485. aminopyridine : Compounds containing a pyridine skeleton substituted by one or more amine groups.	2.71	3
oleanolic acid [no description available]	2	1	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.	2.01	1	3'-hydroxyflavanones; 4'-methoxyflavanones; dihydroxyflavanone; disaccharide derivative; flavanone glycoside; monomethoxyflavanone; rutinoside	mutagen
alpha-naphthoflavone alpha-naphthoflavone: inhibits P4501A1 and P4501A2; stimulates some activities of P4503A4. alpha-naphthoflavone : An extended flavonoid resulting from the formal fusion of a benzene ring with the h side of flavone. A synthetic compound, it is an inhibitor of aromatase (EC 1.14.14.14).	2.38	2	extended flavonoid; naphtho-gamma-pyrone; organic heterotricyclic compound	aryl hydrocarbon receptor agonist; aryl hydrocarbon receptor antagonist; EC 1.14.14.14 (aromatase) inhibitor
2-nitrofluorene 2-nitrofluorene: RN given refers to cpd with locant with nitro moiety in 2 position. 2-nitrofluorene : A nitroarene that is fluorene substituted by a nitro group at position 2.	2.68	3	nitroarene	carcinogenic agent; mutagen
2-anthramine 2-anthramine: structure	2.91	4	anthracenamine
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	1.98	1	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
methylnitrosourea Methylnitrosourea: A nitrosourea compound with alkylating, carcinogenic, and mutagenic properties.. N-methyl-N-nitrosourea : A member of the class of N-nitrosoureas that is urea in which one of the nitrogens is substituted by methyl and nitroso groups.	2.93	4	N-nitrosoureas	alkylating agent; carcinogenic agent; mutagen; teratogenic agent
n-nitrosopyrrolidine N-Nitrosopyrrolidine: Carcinogenic nitrosamine that may be formed from preservatives in meats during their preparation or in the liver during metabolism.	2.71	3	pyrrolidines
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.	1.99	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
guanazole Guanazole: A cytostatic triazole derivative which is not to be confused with guanazolo, the generic name for 8-azaguanine.. guanazole : An aromatic amine that is 1,2,4-triazole substituted at positions 3 and 5 by amino groups.	1.96	1	aromatic amine; triazoles	antineoplastic agent; DNA synthesis inhibitor; EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor
picloram Picloram: A picolinic acid derivative that is used as a herbicide.. picloram : A pyridinemonocarboxylic acid that is pyridine-2-carboxylic acid which is substituted by a chloro group at positions 3,5 and 6, and by an amino group at position 4. It is a systemic herbicide used to control deeply rooted herbaceous weeds and woody plants in rights-of-way, forestry, range lands, pastures, and small grain crops.	1.97	1	aminopyridine; chloropyridine; organochlorine pesticide; pyridinemonocarboxylic acid	herbicide; synthetic auxin
methionine sulfoximine methionine sulfoximine : A non-proteinogenic alpha-amino acid that is the sulfoximine derivative of methionine .	1.96	1	methionine derivative; non-proteinogenic alpha-amino acid; sulfoximide
diallyl disulfide diallyl disulfide: major constituent of garlic oil. diallyl disulfide : An organic disulfide where the organic group specified is allyl. It has been isolated from garlic and other species of the genus Allium.	1.99	1	organic disulfide	antifungal agent; antineoplastic agent; plant metabolite
phenethyl isothiocyanate phenethyl isothiocyanate: a dietary liver aldehyde dehydrogenase inhibitor; promotes urinary bladder carcinoma. phenethyl isothiocyanate : An isothiocyanate having a phenethyl group attached to the nitrogen. It is a naturally occurring compound found in some cruciferous vegetables (e.g. watercress) and is known to possess anticancer properties.	2.73	3	isothiocyanate	antineoplastic agent; EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor; metabolite
captafol captafol: RN given refers to cpd with specified chlorine locants. captafol : A dicarboximide that captan in which the trichloromethyl group is replaced by a 1,1,2,2-tetrachloroethyl group. A broad-spectrum fungicide used to control diseases in fruit and potatoes, it is no longer approved for use in the European Community.	1.98	1	isoindoles; organochlorine compound; organosulfur compound; phthalimide fungicide	antifungal agrochemical
7,12-dihydroxymethylbenz(a)anthracene 7,12-dihydroxymethylbenz(a)anthracene: structure given in first source	2.07	1
buthionine sulfoximine Buthionine Sulfoximine: A synthetic amino acid that depletes glutathione by irreversibly inhibiting gamma-glutamylcysteine synthetase. Inhibition of this enzyme is a critical step in glutathione biosynthesis. It has been shown to inhibit the proliferative response in human T-lymphocytes and inhibit macrophage activation. (J Biol Chem 1995;270(33):1945-7). 2-amino-4-(S-butylsulfonimidoyl)butanoic acid : A non-proteinogenic alpha-amino acid that is homocysteine in which the thiol group carries an oxo, imino and butyl groups.. S-butyl-DL-homocysteine (S,R)-sulfoximine : A sulfoximide that is the sulfoximine derivative of an analogue of DL-methionine in which the S-methyl group is replaced by S-butyl.	1.96	1	diastereoisomeric mixture; homocysteines; non-proteinogenic alpha-amino acid; sulfoximide	EC 6.3.2.2 (glutamate--cysteine ligase) inhibitor; ferroptosis inducer
palladium Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.	2.42	2	metal allergen; nickel group element atom; platinum group metal atom
cadmium Cadmium: An element with atomic symbol Cd, atomic number 48, and atomic weight 112.41. It is a metal and ingestion will lead to CADMIUM POISONING.. elemental cadmium : An element in the zinc group of the periodic table with atomic number 48, atomic mass 112, M.P. 321degreeC, and B.P. 765degreeC). An odourless, tasteless, and highly poisonous soft, ductile, lustrous metal with electropositive properties. It has eight stable isotopes: (106)Cd, (108)Cd,(110)Cd, (111)Cd, (112)Cd, (113)Cd, (114)Cd and (116)Cd, with (112)Cd and (114)Cd being the most common.	2.01	1	cadmium molecular entity; zinc group element atom
galactosamine 2-amino-2-deoxy-D-galactopyranose : The pyranose form of D-galactosamine.. D-galactosamine : The D-stereoisomer of galactosamine.	1.97	1	D-galactosamine; primary amino compound	toxin
ferric chloride ferric chloride: RN given refers to cpd with MF of Fe-Cl3; used to induce experimental arterial thrombosis to evaluate antithrombotic agents	1.97	1	iron coordination entity	astringent; Lewis acid
ferrous sulfate ferrous sulfate: Ferro-Gradumet is ferrous sulfate in controlled release form; RN given refers to Fe(+2)[1:1] salt. iron(2+) sulfate (anhydrous) : A compound of iron and sulfate in which the ratio of iron(2+) to sulfate ions is 1:1. Various hydrates occur naturally - most commonly the heptahydrate, which loses water to form the tetrahydrate at 57degreeC and the monohydrate at 65degreeC.	1.97	1	iron molecular entity; metal sulfate	reducing agent
chlorine Chlorine: An element with atomic symbol Cl, atomic number 17, and atomic weight 35, and member of the halogen family.	1.96	1	diatomic chlorine; gas molecular entity	bleaching agent
3,4,3',4'-tetrachloroazobenzene 3,4,3',4'-tetrachloroazobenzene: unwanted contaminant found in commercial synthesis of dichloroaniline or herbicides made from dichloroaniline; implicated in outbreak of acne in chemical workers; RN given refers to parent cpd; structure	1.96	1
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.	2.38	2	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
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.	2.39	2	benzenes; phenyl acetates
ursodeoxycholic acid Ursodeoxycholic Acid: An epimer of chenodeoxycholic acid. It is a mammalian bile acid found first in the bear and is apparently either a precursor or a product of chenodeoxycholate. Its administration changes the composition of bile and may dissolve gallstones. It is used as a cholagogue and choleretic.. ursodeoxycholic acid : A bile acid found in the bile of bears (Ursidae) as a conjugate with taurine. Used therapeutically, it prevents the synthesis and absorption of cholesterol and can lead to the dissolution of gallstones.. ursodeoxycholate : A bile acid anion that is the conjugate base of ursodeoxycholic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.	2	1	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
alkenes [no description available]	3.07	1
sodium azide Sodium Azide: A cytochrome oxidase inhibitor which is a nitridizing agent and an inhibitor of terminal oxidation. (From Merck Index, 12th ed). sodium azide : The sodium salt of hydrogen azide (hydrazoic acid).	1.99	1	inorganic sodium salt	antibacterial agent; explosive; mitochondrial respiratory-chain inhibitor; mutagen
4-acetylaminofluorene 4-acetylaminofluorene : A member of the class of acetamides that is acetamide in which one of the hydrogens attached to the nitrogen is replaced by a 9H-fluoren-4-yl group.	1.98	1	acetamides; fluorenes	mitogen
4-ipomeanol 4-ipomeanol: lung-toxic furanoterpenoid produced in moldy sweet potatoes in response to fungus infection; RN given refers to cpd without isomeric designation; structure	2.39	2	aromatic ketone
1,6-dinitropyrene [no description available]	1.99	1	pyrenes
1,8-dinitropyrene [no description available]	3.48	2	pyrenes
chlorodiphenyl (54% chlorine) Chlorodiphenyl (54% Chlorine): A mixture of polychlorinated biphenyls that induces hepatic microsomal UDP-glucuronyl transferase activity towards thyroxine.. Aroclor 1254 : A mixture of polychlorobiphenyls of unspecified composition, containing 54% chlorine (X = Cl or H).	4.57	8
diisopropanolnitrosamine diisopropanolnitrosamine: experimental carcinogen. N,N-bis(2-hydroxypropyl)nitrosamine : A nitrosamine that is dipropylamine in which the hydrogen attached to the nitrogen has been replaced by a nitroso group. It is a genotoxic carcinogen, targeting the lung, liver, thyroid, and kidney.	2.03	1	diol; nitrosamine; secondary alcohol	carcinogenic agent
4-(n-methyl-n-nitrosamino)-1-(3-pyridyl)-1-butanone 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone: structure; from tobacco smoke	1.99	1	nitrosamine; pyridines
glu-p-2 Glu-P-2: RN given refers to parent cpd	4.17	5	imidazopyridine
2-amino-6-methyldipyrido(1,2-a-3',2'-d)imidazole 2-amino-6-methyldipyrido(1,2-a-3',2'-d)imidazole: structure	4.46	23	imidazopyridine
adenosine quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit	2.05	1	adenosines; purines D-ribonucleoside	analgesic; anti-arrhythmia drug; fundamental metabolite; human metabolite; vasodilator agent
2-amino-3-methyl-9h-pyrido(2,3-b)indole 2-amino-3-methyl-9H-pyrido(2,3-b)indole: pyrolysis product of soybean globulins; structure	3.07	5	pyridoindole
2-amino-3,4-dimethylimidazo(4,5-f)quinoline 2-amino-3,4-dimethylimidazo(4,5-f)quinoline: strong mutagens found in broiled food; structure given in first source	8.02	69	aminoquinoline
2-amino-3,8-dimethylimidazo(4,5-f)quinoxaline 2-amino-3,8-dimethylimidazo(4,5-f)quinoxaline: strong mutagen found in broiled foods; structure given in first source. MeIQx : An imidazoquinoxaline that is 3H-imidazo[4,5-f]quinoxaline substituted at positions 3 and 8 by methyl groups and at position 2 by an amino group. A mutagenic compound found in cooked beef.	7.33	83	aromatic amine; imidazoquinoxaline	carcinogenic agent; genotoxin; Maillard reaction product; mutagen
isothiocyanic acid [no description available]	2.06	1	hydracid; one-carbon compound
2-amino-9h-pyrido(2,3-b)indole 2-amino-9H-pyrido(2,3-b)indole: pyrolysis product of soybean globulins; RN given refers to unlabeled cpd; structure	3.5	8	pyridoindole
norharman norharman: RN given refers to parent cpd. beta-carboline : The parent compound of the beta-carbolines, a tricyclic structure comprising an indole ring system ortho- fused to C-3 and C-4 of a pyridine ring.	2.76	3	beta-carbolines; mancude organic heterotricyclic parent	fungal metabolite; marine 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.	2.4	2	flavans; gallate ester; polyphenol	antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite
metaperiodate Periodic Acid: A strong oxidizing agent.	1.99	1	iodine 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.	1.96	1	1,2,3-triazole
erucin [no description available]	2.06	1	isothiocyanate
4-aminophenyl-beta-galactoside 4-aminophenyl-beta-galactoside: RN given refers to (beta-D)-isomer	2.05	1
3,4,8-trimethylimidazo(4,5-f)quinoxalin-2-amine 3,4,8-trimethylimidazo(4,5-f)quinoxalin-2-amine: structure given in first source	3.88	12	quinoxaline derivative
2-amino-3,7,8-trimethylimidazo(4,5-f)quinoxaline 2-amino-3,7,8-trimethylimidazo(4,5-f)quinoxaline: mutagen formed by heating mixture of creatinine, glucose & glycine; structure given in first source	2.89	4
2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine: directly acting genotoxic metabolite of 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine. N-hydroxy-PhIP : An imidazopyridine that is 1H--imidazo[4,5-b]pyridine which is substituted at positions 1, 2, and 6 by methyl, hydoxyamino, and phenyl groups, respectively. The active metabolite of the dietary carcinogen PhIP.	2.69	3	hydroxylamine; imidazopyridine	carcinogenic agent; genotoxin; human xenobiotic metabolite; mouse metabolite; mutagen; neurotoxin; rat metabolite
2-hydroxyamino-3-methylimidazolo(4,5-f)quinoline 2-hydroxyamino-3-methylimidazolo(4,5-f)quinoline: major reactive matabolite of mutagen 2-amino-3-methylimidazolo(4,5-f)quinoline in rat liver microsomes; structure in first source	3.37	7	quinolines
pentoxyresorufin [no description available]	1.99	1
epicatechin gallate epicatechin gallate: a steroid 5alpha-reductase inhibitor; RN given refers to the (cis)-isomer; structure given in first source; isolated from green tea. (-)-epicatechin-3-O-gallate : A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of epicatechin. A natural product found in Parapiptadenia rigida.	2.01	1	catechin; gallate ester; polyphenol	EC 3.2.1.1 (alpha-amylase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; metabolite
soyasapogenol b soyasapogenol B: RN given for (3beta,4beta,22beta)-isomer; structure in first source. soyasapogenol B : A pentacyclic triterpenoid that is oleanane containing a double bond between positions 12 and 13 and substituted by hydroxy groups at the 3beta, 22beta and 24-positions.	2	1	pentacyclic triterpenoid
elacridar Elacridar: inhibitor of MDR1 PROTEIN; structure given in first source	2.05	1
2,3-dihydro-3,5-dihydroxy-6-methyl-4h-pyran-4-one 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one: a Maillard reaction product of glucose and glycine; structure in first source	2	1
xylose xylopyranose: structure in first source	1.98	1	D-xylose
proline Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.	1.97	1	amino acid zwitterion; glutamine family amino acid; L-alpha-amino acid; proline; proteinogenic amino acid	algal metabolite; compatible osmolytes; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
metaperiodate metaperiodate: RN given refers to periodic acid, Na salt; structure. periodate : A monovalent inorganic anion obtained by deprotonation of periodic acid.	1.99	1	iodine oxoanion; monovalent inorganic anion
2'-hydroxyflavanone [no description available]	1.98	1
aflatoxin b1 Aflatoxin B1: A potent hepatotoxic and hepatocarcinogenic mycotoxin produced by the Aspergillus flavus group of fungi. It is also mutagenic, teratogenic, and causes immunosuppression in animals. It is found as a contaminant in peanuts, cottonseed meal, corn, and other grains. The mycotoxin requires epoxidation to aflatoxin B1 2,3-oxide for activation. Microsomal monooxygenases biotransform the toxin to the less toxic metabolites aflatoxin M1 and Q1.. aflatoxin B1 : An aflatoxin having a tetrahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h]chromene skeleton with oxygen functionality at positions 1, 4 and 11.	4.13	16	aflatoxin; aromatic ether; aromatic ketone	carcinogenic agent; human metabolite
2,3-dihydro-1h-imidazo(1,2-b)pyrazole 2,3-dihydro-1H-imidazo(1,2-b)pyrazole: inhibitor of DNA synthesis	1.96	1
raffinose Raffinose: A trisaccharide occurring in Australian manna (from Eucalyptus spp, Myrtaceae) and in cottonseed meal.. raffinose : A trisaccharide composed of alpha-D-galactopyranose, alpha-D-glucopyranose and beta-D-fructofuranose joined in sequence by 1->6 and 1<->2 glycosidic linkages, respectively.	2.05	1	raffinose family oligosaccharide; trisaccharide	mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
acetyl coenzyme a Acetyl Coenzyme A: Acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent.	1.96	1	acyl-CoA	acyl donor; coenzyme; effector; fundamental 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.	2.38	2	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
resveratrol trans-resveratrol : A resveratrol in which the double bond has E configuration.	2.01	1	resveratrol	antioxidant; phytoalexin; plant metabolite; quorum sensing inhibitor; radical scavenger
eicosapentaenoic acid icosapentaenoic acid : Any straight-chain, C20 polyunsaturated fatty acid having five C=C double bonds.. all-cis-5,8,11,14,17-icosapentaenoic acid : An icosapentaenoic acid having five cis-double bonds at positions 5, 8, 11, 14 and 17.	1.98	1	icosapentaenoic acid; omega-3 fatty acid	anticholesteremic drug; antidepressant; antineoplastic agent; Daphnia galeata metabolite; fungal metabolite; micronutrient; mouse metabolite; nutraceutical
lycopene [no description available]	2.72	3	acyclic carotene	antioxidant; plant metabolite
diethylstilbestrol Diethylstilbestrol: A synthetic nonsteroidal estrogen used in the treatment of menopausal and postmenopausal disorders. It was also used formerly as a growth promoter in animals. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), diethylstilbestrol has been listed as a known carcinogen. (Merck, 11th ed). diethylstilbestrol : An olefinic compound that is trans-hex-3-ene in which the hydrogens at positions 3 and 4 have been replaced by p-hydroxyphenyl groups.	1.98	1	olefinic compound; polyphenol	antifungal agent; antineoplastic agent; autophagy inducer; calcium channel blocker; carcinogenic agent; EC 1.1.1.146 (11beta-hydroxysteroid dehydrogenase) inhibitor; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; endocrine disruptor; xenoestrogen
bromochloroacetic acid Keratins: A class of fibrous proteins or scleroproteins that represents the principal constituent of EPIDERMIS; HAIR; NAILS; horny tissues, and the organic matrix of tooth ENAMEL. Two major conformational groups have been characterized, alpha-keratin, whose peptide backbone forms a coiled-coil alpha helical structure consisting of TYPE I KERATIN and a TYPE II KERATIN, and beta-keratin, whose backbone forms a zigzag or pleated sheet structure. alpha-Keratins have been classified into at least 20 subtypes. In addition multiple isoforms of subtypes have been found which may be due to GENE DUPLICATION.. bromochloroacetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is replaced by bromine while a second is replaced by chlorine. A low-melting (27.5-31.5degreeC), hygroscopic crystalline solid, it can be formed during the disinfection (by chlorination) of water that contains bromide ions and organic matter, so can occur in drinking water as a byproduct of the disinfection process.	1.99	1	2-bromocarboxylic acid; monocarboxylic acid; organochlorine compound
cinnamaldehyde 3-phenylprop-2-enal : A member of the class of cinnamaldehydes that is prop-2-enal in which a hydrogen at position 3 has been replaced by a phenyl group. The configuration of the double bond is not specified; the name "cinnamaldehyde" is widely used to refer to the E (trans) isomer.. (E)-cinnamaldehyde : The E (trans) stereoisomer of cinnamaldehyde, the parent of the class of cinnamaldehydes.	1.99	1	3-phenylprop-2-enal; cinnamaldehydes	antifungal agent; EC 4.3.1.24 (phenylalanine ammonia-lyase) inhibitor; flavouring agent; hypoglycemic agent; plant metabolite; sensitiser; vasodilator agent
chalcone trans-chalcone : The trans-isomer of chalcone.	1.98	1	chalcone	EC 3.2.1.1 (alpha-amylase) inhibitor
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	2.01	1	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.	2.73	3	aromatic ether; chalcones; polyphenol	anti-HIV-1 agent; antineoplastic agent; antiviral agent; apoptosis inducer; EC 2.3.1.20 (diacylglycerol O-acyltransferase) inhibitor; metabolite
thiohydantoins Thiohydantoins: Sulfur analogs of hydantoins with one or both carbonyl groups replaced by thiocarbonyl groups.	2.02	1
methimazole Methimazole: A thioureylene antithyroid agent that inhibits the formation of thyroid hormones by interfering with the incorporation of iodine into tyrosyl residues of thyroglobulin. This is done by interfering with the oxidation of iodide ion and iodotyrosyl groups through inhibition of the peroxidase enzyme.. methimazole : A member of the class of imidazoles that it imidazole-2-thione in which a methyl group replaces the hydrogen which is attached to a nitrogen.	1.96	1	1,3-dihydroimidazole-2-thiones	antithyroid drug
D-fructopyranose [no description available]	1.98	1	cyclic hemiketal; D-fructose; fructopyranose	sweetening agent
1,3-dihydroxy-4,4,5,5-tetramethyl-2-(4-carboxyphenyl)tetrahydroimidazole 1,3-dihydroxy-4,4,5,5-tetramethyl-2-(4-carboxyphenyl)tetrahydroimidazole: intermediate in the synthesis of imidazolineoxyl N-oxides; partial structure given in first source	2.03	1	benzoic acid; imidazolines; organic radical	apoptosis inhibitor; radical scavenger
nadp [no description available]	3.79	3
2-nitro-3-methylimidazo(4,5-f)quinoline 2-nitro-3-methylimidazo(4,5-f)quinoline: structure given in first source	2.9	4
mtt formazan MTT formazan: a blue MEM-insoluble mitochondrial byproduct; used to determine viability of cells with active mitochondrial dehydrogenase enzymes	1.98	1
quercetin [no description available]	2.72	3	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
linoleic acid Linoleic Acid: A doubly unsaturated fatty acid, occurring widely in plant glycosides. It is an essential fatty acid in mammalian nutrition and is used in the biosynthesis of prostaglandins and cell membranes. (From Stedman, 26th ed). linoleic acid : An octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry.	3.09	5	octadecadienoic acid; omega-6 fatty acid	algal metabolite; Daphnia galeata metabolite; plant metabolite
vitamin k semiquinone radical vitamin K semiquinone radical: found in active preparations of vitamin K-dependent carboxylase. vitamin K : Any member of a group of fat-soluble 2-methyl-1,4-napthoquinones that exhibit biological activity against vitamin K deficiency. Vitamin K is required for the synthesis of prothrombin and certain other blood coagulation factors.	1.99	1
beta carotene beta Carotene: A carotenoid that is a precursor of VITAMIN A. Beta carotene is administered to reduce the severity of photosensitivity reactions in patients with erythropoietic protoporphyria (PORPHYRIA, ERYTHROPOIETIC).. provitamin A : A provitamin that can be converted into vitamin A by enzymes from animal tissues.	1.99	1	carotenoid beta-end derivative; cyclic carotene	antioxidant; biological pigment; cofactor; ferroptosis inhibitor; human metabolite; mouse metabolite; plant metabolite; provitamin A
rutin Hydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders.	2.07	1	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite
kaempferol [no description available]	2.01	1	7-hydroxyflavonol; flavonols; tetrahydroxyflavone	antibacterial agent; geroprotector; human blood serum metabolite; human urinary metabolite; human xenobiotic metabolite; plant metabolite
harmine Harmine: Alkaloid isolated from seeds of PEGANUM HARMALA; ZYGOPHYLLACEAE. It is identical to banisterine, or telepathine, from Banisteria caapi and is one of the active ingredients of hallucinogenic drinks made in the western Amazon region from related plants. It has no therapeutic use, but (as banisterine) was hailed as a cure for postencephalitic PARKINSON DISEASE in the 1920's.. harmine : A harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7.	2.76	3	harmala alkaloid	anti-HIV agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; metabolite
genistein [no description available]	2.01	1	7-hydroxyisoflavones	antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; geroprotector; human urinary metabolite; phytoestrogen; plant metabolite; tyrosine kinase inhibitor
harman harman: a beta-carboline; RN given refers to parent cpd; structure. harman : An indole alkaloid fundamental parent with a structure of 9H-beta-carboline carrying a methyl substituent at C-1. It has been isolated from the bark of Sickingia rubra, Symplocus racemosa, Passiflora incarnata, Peganum harmala, Banisteriopsis caapi and Tribulus terrestris, as well as from tobacco smoke. It is a specific, reversible inhibitor of monoamine oxidase A.	2.76	3	harmala alkaloid; indole alkaloid fundamental parent; indole alkaloid	anti-HIV agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; plant metabolite
ellagic acid [no description available]	1.98	1	catechols; cyclic ketone; lactone; organic heterotetracyclic compound; polyphenol	antioxidant; EC 1.14.18.1 (tyrosinase) inhibitor; EC 2.3.1.5 (arylamine N-acetyltransferase) inhibitor; EC 2.4.1.1 (glycogen phosphorylase) inhibitor; EC 2.5.1.18 (glutathione transferase) inhibitor; EC 2.7.1.127 (inositol-trisphosphate 3-kinase) inhibitor; EC 2.7.1.151 (inositol-polyphosphate multikinase) inhibitor; EC 2.7.4.6 (nucleoside-diphosphate kinase) inhibitor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; EC 5.99.1.2 (DNA topoisomerase) inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; food additive; fungal metabolite; geroprotector; plant metabolite; skin lightening agent
3-amino-1,4-dimethyl-5h-pyrido(4,3-b)indole 3-amino-1,4-dimethyl-5H-pyrido(4,3-b)indole: structure	4.23	18	pyridoindole
3-amino-1-methyl-5h-pyrido(4,3-b)indole 3-amino-1-methyl-5H-pyrido(4,3-b)indole: structure	5.61	18	pyridoindole
cytochalasin b Cytochalasin B: A cytotoxic member of the CYTOCHALASINS.. cytochalasin B : An organic heterotricyclic compound, that is a mycotoxin which is cell permeable an an inhibitor of cytoplasmic division by blocking the formation of contractile microfilaments.	2.01	1	cytochalasin; lactam; lactone; organic heterotricyclic compound	actin polymerisation inhibitor; metabolite; mycotoxin; platelet aggregation inhibitor
8-oxo-7,8-dihydrodeoxyguanine 8-oxo-7,8-dihydrodeoxyguanine: structure given in first source	2.03	1
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	2.02	1	cysteinium	fundamental metabolite
selenium Selenium: An element with the atomic symbol Se, atomic number 34, and atomic weight 78.97. It is an essential micronutrient for mammals and other animals but is toxic in large amounts. Selenium protects intracellular structures against oxidative damage. It is an essential component of GLUTATHIONE PEROXIDASE.	2.01	1	chalcogen; nonmetal atom	micronutrient
1-(1-glycero)tetradeca-1,3,5,7,9-pentaene 1-(1-glycero)tetradeca-1,3,5,7,9-pentaene: fecapentaene mutagen of bacterial origin from human feces; structure given in first source	3.07	1
glucotropeolin [no description available]	2	1	aralkylglucosinolic acid; benzenes
beta-escin [no description available]	2	1
4-methyl-5-amino-1-formylisoquinoline thiosemicarbazone 4-methyl-5-amino-1-formylisoquinoline thiosemicarbazone: structure	1.96	1
phosphocreatine Phosphocreatine: An endogenous substance found mainly in skeletal muscle of vertebrates. It has been tried in the treatment of cardiac disorders and has been added to cardioplegic solutions. (Reynolds JEF(Ed): Martindale: The Extra Pharmacopoeia (electronic version). Micromedex, Inc, Englewood, CO, 1996). phosphagen : Any of a group of guanidine or amidine phosphates that function as storage depots for high-energy phosphate in muscle with the purpose of regenerating ATP from ADP during muscular contraction.. N-phosphocreatine : A phosphoamino acid consisting of creatine having a phospho group attached at the primary nitrogen of the guanidino group.	1.96	1	phosphagen; phosphoamino acid	human metabolite; mouse metabolite
formazans Formazans: Colored azo compounds formed by the reduction of tetrazolium salts. Employing this reaction, oxidoreductase activity can be determined quantitatively in tissue sections by allowing the enzymes to act on their specific substrates in the presence of tetrazolium salts.	1.98	1
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).	1.96	1	aminopyrimidine; benzamides; pyridines; secondary amino compound; secondary carboxamide; substituted aniline	antineoplastic agent; apoptosis inducer; autophagy inducer; cardioprotective agent; EC 3.5.1.98 (histone deacetylase) inhibitor; hepatotoxic agent
phosphoramidite phosphoramidite: structure in first source. phosphoramidite : A compound with the general formula (RO)2PNR2. Phosphoramidites can be regarded as phosphites that have an NR2 instead of an OH group, or as amides of phosphorous acid.	2.03	1
glycoursodeoxycholic acid glycoursodeoxycholic acid : A bile acid glycine conjugate derived from ursoodeoxycholic acid.. glycoursodeoxycholate : A N-acylglycinate that is the conjugate base of glycoursodeoxycholic acid. obtained by deprotonation of the carboxy group; major species at pH 7.3.	2	1	bile acid glycine conjugate; N-acylglycine	human blood serum metabolite; neuroprotective agent
cyanidin-3-o-beta-glucopyranoside cyanidin-3-O-beta-glucopyranoside: a natural compound distributed in several fruits & vegetables, such as strawberry, rhubarb, cherry, red cabbage, red onion, cranberries, etc.	2.31	1
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	2.38	2	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
oligonucleotides [no description available]	2.94	4
cellulose DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.	2.02	1	glycoside
sodium borate borax: see also sodium borate. borax : A hydrate that is the decahydrate form of disodium tetraborate.	1.99	1
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.	2.4	2	chlorophyll; methyl ester	cofactor
sodium nitrite Sodium Nitrite: Nitrous acid sodium salt. Used in many industrial processes, in meat curing, coloring, and preserving, and as a reagent in ANALYTICAL CHEMISTRY TECHNIQUES. It is used therapeutically as an antidote in cyanide poisoning. The compound is toxic and mutagenic and will react in vivo with secondary or tertiary amines thereby producing highly carcinogenic nitrosamines.. sodium nitrite : An inorganic sodium salt having nitrite as the counterion. Used as a food preservative and antidote to cyanide poisoning.	2.03	1	inorganic sodium salt; nitrite salt	antidote to cyanide poisoning; antihypertensive agent; antimicrobial food preservative; food antioxidant; poison
chiniofon Hydroxyquinolines: The 8-hydroxy derivatives inhibit various enzymes and their halogenated derivatives, though neurotoxic, are used as topical anti-infective agents, among other uses.	2.9	4
2,4-dichloro-6-phenylphenoxyethylamine 2,4-dichloro-6-phenylphenoxyethylamine: RN given refers to parent cpd; structure	1.96	1
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	2.41	2	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
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.	2.39	2	benzenes; hydroxycoumarin; methyl ketone
4-hydroxycoumarin 2-hydroxychromone: structure	2.02	1	hydroxycoumarin
transforming growth factor beta Transforming Growth Factor beta: A factor synthesized in a wide variety of tissues. It acts synergistically with TGF-alpha in inducing phenotypic transformation and can also act as a negative autocrine growth factor. TGF-beta has a potential role in embryonal development, cellular differentiation, hormone secretion, and immune function. TGF-beta is found mostly as homodimer forms of separate gene products TGF-beta1, TGF-beta2 or TGF-beta3. Heterodimers composed of TGF-beta1 and 2 (TGF-beta1.2) or of TGF-beta2 and 3 (TGF-beta2.3) have been isolated. The TGF-beta proteins are synthesized as precursor proteins.	2.07	1
okadaic acid Okadaic Acid: A specific inhibitor of phosphoserine/threonine protein phosphatase 1 and 2a. It is also a potent tumor promoter. It is produced by DINOFLAGELLATES and causes diarrhetic SHELLFISH POISONING.. okadaic acid : A polycyclic ether that is produced by several species of dinoflagellates, and is known to accumulate in both marine sponges and shellfish. A polyketide, polyether derivative of a C38 fatty acid, it is one of the primary causes of diarrhetic shellfish poisoning (DSP). It is a potent inhibitor of specific protein phosphatases and is known to have a variety of negative effects on cells.	1.97	1	ketal
3-(6-isobutyl-9-methoxy-1,4-dioxo-1,2,3,4,6,7,12,12a-octahydropyrazino(1',2'-1,6)pyrido(3,4-b)indol-3-yl)propionic acid tert-butyl ester 3-(6-isobutyl-9-methoxy-1,4-dioxo-1,2,3,4,6,7,12,12a-octahydropyrazino(1',2'-1,6)pyrido(3,4-b)indol-3-yl)propionic acid tert-butyl ester: a breast cancer resistance protein (BCRP) inhibitor; structure in first source	2.05	1
cyclin d1 Cyclin D1: Protein encoded by the bcl-1 gene which plays a critical role in regulating the cell cycle. Overexpression of cyclin D1 is the result of bcl-1 rearrangement, a t(11;14) translocation, and is implicated in various neoplasms.	2	1
thearubigin thearubigin: from black tea leaves; a catechin oxidized product; a mixture of heterogenous polyphenols	1.99	1
nitrophenols Nitrophenols: PHENOLS carrying nitro group substituents.	2.07	1
transforming growth factor alpha Transforming Growth Factor alpha: An EPIDERMAL GROWTH FACTOR related protein that is found in a variety of tissues including EPITHELIUM, and maternal DECIDUA. It is synthesized as a transmembrane protein which can be cleaved to release a soluble active form which binds to the EGF RECEPTOR.	2.4	2
deoxyguanosine [no description available]	3.88	12	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
guanine [no description available]	2.69	3	2-aminopurines; oxopurine; purine nucleobase	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
rifampin Rifampin: A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)	1.98	1	cyclic ketal; hydrazone; N-iminopiperazine; N-methylpiperazine; rifamycins; semisynthetic derivative; zwitterion	angiogenesis inhibitor; antiamoebic agent; antineoplastic agent; antitubercular agent; DNA synthesis inhibitor; EC 2.7.7.6 (RNA polymerase) inhibitor; Escherichia coli metabolite; geroprotector; leprostatic drug; neuroprotective agent; pregnane X receptor agonist; protein synthesis inhibitor
methylnitronitrosoguanidine Methylnitronitrosoguanidine: A nitrosoguanidine derivative with potent mutagenic and carcinogenic properties.. N-methyl-N'-nitro-N-nitrosoguanidine : An N-nitroguanidine compound having nitroso and methyl substituents at the N'-position	2.7	3	nitroso compound	alkylating agent
8-hydroxy-2'-deoxyguanosine 8-Hydroxy-2'-Deoxyguanosine: Common oxidized form of deoxyguanosine in which C-8 position of guanine base has a carbonyl group.. 8-hydroxy-2'-deoxyguanosine : Guanosine substituted at the purine 8-position by a hydroxy group. It is used as a biomarker of oxidative DNA damage.	2.42	2	guanosines	biomarker
concanavalin a Concanavalin A: A MANNOSE/GLUCOSE binding lectin isolated from the jack bean (Canavalia ensiformis). It is a potent mitogen used to stimulate cell proliferation in lymphocytes, primarily T-lymphocyte, cultures.	1.99	1
metallothionein Metallothionein: A low-molecular-weight (approx. 10 kD) protein occurring in the cytoplasm of kidney cortex and liver. It is rich in cysteinyl residues and contains no aromatic amino acids. Metallothionein shows high affinity for bivalent heavy metals.	2.01	1
phosphorus radioisotopes Phosphorus Radioisotopes: Unstable isotopes of phosphorus that decay or disintegrate emitting radiation. P atoms with atomic weights 28-34 except 31 are radioactive phosphorus isotopes.	3.68	10

Condition	Relationship Strength	Studies
Acute Liver Injury, Drug-Induced [description not available]	2.72	2
Innate Inflammatory Response [description not available]	2.31	1
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	2.31	1
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.	2.72	2
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.	2.17	1
Colitis Gravis [description not available]	3	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	4.32	7
Colorectal Cancer [description not available]	4.17	6
Colitis Inflammation of the COLON section of the large intestine (INTESTINE, LARGE), usually with symptoms such as DIARRHEA (often with blood and mucus), ABDOMINAL PAIN, and FEVER.	3	1
Colitis, Ulcerative Inflammation of the COLON that is predominantly confined to the MUCOSA. Its major symptoms include DIARRHEA, rectal BLEEDING, the passage of MUCUS, and ABDOMINAL PAIN.	3	1
Colorectal Neoplasms Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.	4.17	6
Cancer of Colon [description not available]	5.72	32
Cancer of Liver [description not available]	4.44	22
Condition, Preneoplastic [description not available]	4.25	18
Colonic Neoplasms Tumors or cancer of the COLON.	5.72	32
Liver Neoplasms Tumors or cancer of the LIVER.	4.44	22
Precancerous Conditions Pathological conditions that tend eventually to become malignant.	4.25	18
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	4.02	5
Benign Neoplasms [description not available]	4.63	6
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.	4.63	6
Aberrant Crypt Foci Clusters of colonic crypts that appear different from the surrounding mucosa when visualized after staining. They are of interest as putative precursors to colorectal adenomas and potential biomarkers for colorectal carcinoma.	2.06	1
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	4.35	20
Cell Transformation, Neoplastic Cell changes manifested by escape from control mechanisms, increased growth potential, alterations in the cell surface, karyotypic abnormalities, morphological and biochemical deviations from the norm, and other attributes conferring the ability to invade, metastasize, and kill.	3.6	9
Hepatocellular Carcinoma [description not available]	3.87	12
Experimental Hepatoma [description not available]	6.45	27
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.	3.87	12
Experimental Neoplasms [description not available]	4.84	13
Cancer of Skin [description not available]	4.28	7
Skin Neoplasms Tumors or cancer of the SKIN.	4.28	7
Cancer of Intestines [description not available]	4	5
Intestinal Neoplasms Tumors or cancer of the INTESTINES.	4	5
A-Thalassemia [description not available]	2.42	2
Anemia, Cooley's [description not available]	2.42	2
alpha-Thalassemia A disorder characterized by reduced synthesis of the alpha chains of hemoglobin. The severity of this condition can vary from mild anemia to death, depending on the number of genes deleted.	2.42	2
beta-Thalassemia A disorder characterized by reduced synthesis of the beta chains of hemoglobin. There is retardation of hemoglobin A synthesis in the heterozygous form (thalassemia minor), which is asymptomatic, while in the homozygous form (thalassemia major, Cooley's anemia, Mediterranean anemia, erythroblastic anemia), which can result in severe complications and even death, hemoglobin A synthesis is absent.	2.42	2
Weight Gain Increase in BODY WEIGHT over existing weight.	2.41	2
Adenocarcinoma, Basal Cell [description not available]	3.37	7
Adenoma, Basal Cell [description not available]	3.08	5
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	3.37	7
Adenoma A benign epithelial tumor with a glandular organization.	3.08	5
Chromosome-Defective Micronuclei [description not available]	2.41	2
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)	3.1	5
Adenoma, Hepatocellular [description not available]	2.03	1
Cancer of Lung [description not available]	5.2	7
Lung Neoplasms Tumors or cancer of the LUNG.	5.2	7
Diathesis [description not available]	2.44	2
Papilloma, Squamous Cell [description not available]	2.4	2
Cancer of Stomach [description not available]	3.08	5
Hyperplasia An increase in the number of cells in a tissue or organ without tumor formation. It differs from HYPERTROPHY, which is an increase in bulk without an increase in the number of cells.	2.4	2
Papilloma A circumscribed benign epithelial tumor projecting from the surrounding surface; more precisely, a benign epithelial neoplasm consisting of villous or arborescent outgrowths of fibrovascular stroma covered by neoplastic cells. (Stedman, 25th ed)	2.4	2
Stomach Neoplasms Tumors or cancer of the STOMACH.	3.08	5
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	2.4	2
Carcinoma, Epidermoid [description not available]	3.08	5
Carcinoma, Squamous Cell A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed)	3.08	5
Leukemia L 1210 [description not available]	1.96	1
Carcinoma, Anaplastic [description not available]	2.66	3
Carcinoma A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.	2.66	3
Academic Disorder, Developmental [description not available]	1.96	1
Learning Disabilities Conditions characterized by a significant discrepancy between an individual's perceived level of intellect and their ability to acquire new language and other cognitive skills. These may result from organic or psychological conditions. Relatively common subtypes include DYSLEXIA, DYSCALCULIA, and DYSGRAPHIA.	1.96	1
Experimental Leukemia [description not available]	1.96	1
Abnormalities, Autosome [description not available]	3.07	5
Cardiac Diseases [description not available]	2.39	2
Heart Diseases Pathological conditions involving the HEART including its structural and functional abnormalities.	2.39	2
Cirrhosis [description not available]	1.98	1
Cardiac Hypertrophy Enlargement of the HEART due to chamber HYPERTROPHY, an increase in wall thickness without an increase in the number of cells (MYOCYTES, CARDIAC). It is the result of increase in myocyte size, mitochondrial and myofibrillar mass, as well as changes in extracellular matrix.	1.98	1
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	1.98	1
Cardiomegaly Enlargement of the HEART, usually indicated by a cardiothoracic ratio above 0.50. Heart enlargement may involve the right, the left, or both HEART VENTRICLES or HEART ATRIA. Cardiomegaly is a nonspecific symptom seen in patients with chronic systolic heart failure (HEART FAILURE) or several forms of CARDIOMYOPATHIES.	1.98	1
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	1.98	1
Neoplasms, Sebaceous Gland [description not available]	2.38	2
Auricular Cancer [description not available]	2.66	3
Ear Neoplasms Tumors or cancer of any part of the hearing and equilibrium system of the body (the EXTERNAL EAR, the MIDDLE EAR, and the INNER EAR).	2.66	3
Experimental Mammary Neoplasms [description not available]	4.4	8
Cocarcinogenesis The combination of two or more different factors in the production of cancer.	2.38	2
Cancer of Rectum [description not available]	2.9	1
Rectal Neoplasms Tumors or cancer of the RECTUM.	2.9	1
Metastase [description not available]	2.67	3
Angiogenesis, Pathologic [description not available]	1.99	1
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	2.67	3
Invasiveness, Neoplasm [description not available]	1.98	1
Germinoblastoma [description not available]	2.39	2
Lymphoma A general term for various neoplastic diseases of the lymphoid tissue.	2.39	2
Fibroadenoma An adenoma containing fibrous tissue. It should be differentiated from ADENOFIBROMA which is a tumor composed of connective tissue (fibroma) containing glandular (adeno-) structures. (From Dorland, 27th ed)	1.99	1
Colonic Diseases Pathological processes in the COLON region of the large intestine (INTESTINE, LARGE).	1.99	1
Breast Cancer [description not available]	2.4	2
Breast Neoplasms Tumors or cancer of the human BREAST.	2.4	2
Bare Lymphocyte Syndrome [description not available]	2	1
Severe Combined Immunodeficiency Group of rare congenital disorders characterized by impairment of both humoral and cell-mediated immunity, leukopenia, and low or absent antibody levels. It is inherited as an X-linked or autosomal recessive defect. Mutations occurring in many different genes cause human Severe Combined Immunodeficiency (SCID).	2	1
Delayed Effects, Prenatal Exposure [description not available]	2	1
Adenoma, Prostatic [description not available]	2	1
Prostatic Hyperplasia Increase in constituent cells in the PROSTATE, leading to enlargement of the organ (hypertrophy) and adverse impact on the lower urinary tract function. This can be caused by increased rate of cell proliferation, reduced rate of cell death, or both.	2	1
Adenosarcoma A malignant neoplasm arising simultaneously or consecutively in mesodermal tissue and glandular epithelium of the same part. (Stedman, 25th ed)	2	1
Deficiency, Ascorbic Acid [description not available]	1.97	1
Ascorbic Acid Deficiency A condition due to a dietary deficiency of ascorbic acid (vitamin C), characterized by malaise, lethargy, and weakness. As the disease progresses, joints, muscles, and subcutaneous tissues may become the sites of hemorrhage. Ascorbic acid deficiency frequently develops into SCURVY in young children fed unsupplemented cow's milk exclusively during their first year. It develops also commonly in chronic alcoholism. (Cecil Textbook of Medicine, 19th ed, p1177)	1.97	1
Cancer of Gastrointestinal Tract [description not available]	2.89	1
Uremia A clinical syndrome associated with the retention of renal waste products or uremic toxins in the blood. It is usually the result of RENAL INSUFFICIENCY. Most uremic toxins are end products of protein or nitrogen CATABOLISM, such as UREA or CREATININE. Severe uremia can lead to multiple organ dysfunctions with a constellation of symptoms.	2.37	2
Alloxan Diabetes [description not available]	1.97	1
Cancer of the Thyroid [description not available]	1.97	1
Thyroid Neoplasms Tumors or cancer of the THYROID GLAND.	1.97	1
Cancer of the Thymus [description not available]	2.88	1
Fibrosarcoma A sarcoma derived from deep fibrous tissue, characterized by bundles of immature proliferating fibroblasts with variable collagen formation, which tends to invade locally and metastasize by the bloodstream. (Stedman, 25th ed)	2.88	1
Thymus Neoplasms Tumors or cancer of the THYMUS GLAND.	2.88	1
Granulomas [description not available]	1.97	1
Granuloma A relatively small nodular inflammatory lesion containing grouped mononuclear phagocytes, caused by infectious and noninfectious agents.	1.97	1
Alcohol Abuse [description not available]	1.96	1
Aprosodia [description not available]	1.96	1
Hemisensory Neglect [description not available]	1.96	1
Acoustic Perceptual Disorder [description not available]	1.96	1
Alcoholism A primary, chronic disease with genetic, psychosocial, and environmental factors influencing its development and manifestations. The disease is often progressive and fatal. It is characterized by impaired control over drinking, preoccupation with the drug alcohol, use of alcohol despite adverse consequences, and distortions in thinking, most notably denial. Each of these symptoms may be continuous or periodic. (Morse & Flavin for the Joint Commission of the National Council on Alcoholism and Drug Dependence and the American Society of Addiction Medicine to Study the Definition and Criteria for the Diagnosis of Alcoholism: in JAMA 1992;268:1012-4)	1.96	1
Perceptual Disorders Cognitive disorders characterized by an impaired ability to perceive the nature of objects or concepts through use of the sense organs. These include spatial neglect syndromes, where an individual does not attend to visual, auditory, or sensory stimuli presented from one side of the body.	1.96	1
Cancer of Pancreas [description not available]	1.96	1
Pancreatic Neoplasms Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).	1.96	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).	1.96	1

2-amino-3-methylimidazo(4,5-f)quinoline

Description

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Synonyms (53)

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Roles (1)

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Protein Targets (12)

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Studies (463)

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Research Demand Index: 17.57

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