2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine profile

2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine: mutagen from fried ground beef; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

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. [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	1530
CHEMBL ID	1213271
CHEBI ID	76290
SCHEMBL ID	151718
MeSH ID	M0142001

Synonym
CHEMBL1213271
2-amino-1-methyl-6- phenylimidazo[4,5- b]pyridine
chebi:76290 ,
105650-23-5
1-methyl-6-phenyl-1h-imidazo[4,5-b]pyridin-2-amine
phip
2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine
PIQ ,
2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine
2-amino-1methyl-6-phenylimidazo [4,5-b]pyridine (phip)
2-amino-1-methyl-6-phenyl-imidazo [4,5-b] pyridine
DB08398
FT-0661932
FT-0661933
1-methyl-6-phenylimidazo[4,5-b]pyridin-2-amine
A801292
(3h)phip
1h-imidazo(4,5-b)pyridin-2-amine, 1-methyl-6-phenyl-, labeled with tritium
138370-35-1
1h-imidazo(4,5-b)pyridine, 2-amino-1-methyl-6-phenyl-
ccris 2954
1-methyl-6-phenyl-1h-imidazo(4,5-b)pyridin-2-amine
hsdb 7768
brn 5951264
unii-909c6un66t
909c6un66t ,
1h-imidazo(4,5-b)pyridin-2-amine, 1-methyl-6-phenyl-
imidazo(4,5-b)pyridine, 2-amino-1-methyl-6-phenyl-
FT-0611009
amino-1-methyl-6-phenylimidazo(4,5-b)pyridine, 2-
phip [mi]
phip [iarc]
2-amino-1-methyl-6-phenyl-1h-imidazo(4,5-b)pyridine
2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine [hsdb]
AKOS022175457
SCHEMBL151718
mfcd00210745
2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine
DTXSID3037628 ,
J-507739
1h-imidazo(4,5-b)pyridin-2-amine, 1-methyl-6-phenyl- (9ci)
2-amino-1-methyl-6-phenyl-imidazo(4,5-b)pyridine
2-amino-1-methyl-6-phenyl-1h-imidazo[4,5-b]pyridine
2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine (phip)
1-methyl-6-phenyl-1h-imidazo[4,5-b]pyridin-2-amine, 9ci
1185024-97-8
Q4596855
HY-118716
2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (phip)
CS-0068303
MS-23263
?-phenyl-2-pyridineacetamide-d4
dtxcid1017628
phip (iarc)
2-amino-1methyl-6-phenylimidazo (4,5-b)pyridine

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
" In this study, changes of 2-amino-1-methyl-6-phenylimidazo[4,5-b] pyridine (PhIP)-DNA adduct formations in the liver, colon and lung, as assessed by the 32P-postlabeling method and immunohistochemical analysis, and carcinogenic and/or toxic susceptibility of both sexes of XPA-deficient mice (XPA-/-) to PhIP, which is a carcinogenic heterocyclic amine, was examined."	( Delay of DNA-adduct repair and severe toxicity in xeroderma pigmentosum group A gene (XPA) deficient mice treated with 2-amino-1-methyl-6-phenyl-imidazo [4,5-b] pyridine (PhIP). Imaida, K; Ito, N; Ito, T; Ogawa, K; Shirai, T; Takahashi, S; Tanaka, K; Totsuka, Y; Wakabayashi, K; Yamaguchi, T, 2000)	0.31
" The results show that PhIP is extremely toxic to XPA(-/-) mice, even at doses 10-fold lower than tolerated by wild-type C57BL/6 mice."	( Intestinal toxicity and carcinogenic potential of the food mutagen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in DNA repair deficient XPA-/- mice. Beems, RB; Hamzink, M; Klein, JC; van Kreijl, CF; van Steeg , H; Zomer, G; Zwart, PE, 2001)	0.31
" However, the toxic effects and related mechanisms of co-exposure to HAA in humans remain unknown."	( Differential toxicity of heterocyclic aromatic amines and their mixture in metabolically competent HepaRG cells. Aninat, C; Anthérieu, S; Dumont, J; Guguen-Guillouzo, C; Guillouzo, A; Jossé, R; Lambert, C; Le Hegarat, L; Robin, MA, 2010)	0.36
" If formed in vivo, ABAQ may give rise to adverse genotoxic effects."	( In vivo genotoxicity of a novel heterocyclic amine, aminobenzoazepinoquinolinone-derivative (ABAQ), produced by the Maillard reaction between glucose and l-tryptophan. Coulibaly, S; Hasei, T; Kobayashi, S; Nakagama, H; Nishizaki, M; Okazaki, M; Totsuka, Y; Wakabayashi, K; Watanabe, T, 2014)	0.4
" These results suggest that neuromelanin has a critical role in HAA toxicity and adverse effects on mitochondria."	( Neuromelanin formation exacerbates HAA-induced mitochondrial toxicity and mitophagy impairments. Cannon, JR; Foguth, RM; Lawana, V; Um, SY, 2020)	0.56

Excerpt	Reference	Relevance
" In the present study, groups of 6-week-old F344 and ACI male rats, the former strain being susceptible to colon carcinogenesis induced by 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) and the latter being relatively resistant, were subjected to a long-term carcinogenesis experiment using our intermittent feeding protocol of PhIP in combination with a high-fat diet, which serves as a relevant risk factor that promotes the development of colon cancers."	( Differential gene expression profiles in colon epithelium of two rat strains with distinct susceptibility to colon carcinogenesis after exposure to PhIP in combination with dietary high fat. Fujiwara, K; Nagao, M; Nakagama, H; Ochiai, M; Ohki, M; Ohta, T; Sugimura, T; Ubagai, T, 2003)	0.32

Excerpt	Reference	Relevance
" The variability in relative systemic bioavailability was assessed from the percentage of ingested amine excreted unchanged in the urine."	( Intra- and interindividual variability in systemic exposure in humans to 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline and 2-amino-1-methyl- 6-phenylimidazo[4,5-b]pyridine, carcinogens present in cooked beef. Boobis, AR; Davies, DS; Gooderham, NJ; Knize, MG; Lynch, AM; Murray, S, 1992)	0.28
" We report the first study of the bioavailability and fate of this heterocyclic amine at a human dietary equivalent dose using the high sensitivity offered by accelerator mass spectrometry."	( Fate and distribution of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in mice at a human dietary equivalent dose. Frantz, CE; Shen, N; Turteltaub, KW; Vogel, JS, 1992)	0.28
"The bioavailability and the bioreactivity of the carcinogenic heterocyclic amine [2-14C]2-amino-1-methyl-6-phenyl-imidazo[4,5-b]pyridine (PhIP) have been investigated at a dose approximating that likely from the human diet by accelerator mass spectrometry (AMS)."	( Low-level biological dosimetry of heterocyclic amine carcinogens isolated from cooked food. Buonarati, MH; Felton, JS; Frantz, C; Turteltaub, KW; Vogel, JS, 1993)	0.29
" Studies using these assays have demonstrated that both MeIQx and PhIP are well absorbed and extensively metabolised following ingestion of amine-containing beef by humans."	( Chemical methods for assessing systemic exposure to dietary heterocyclic amines in man. Boobis, AR; Davies, DS; de la Torre, R; Gooderham, NJ; Lynch, A; Murray, S; Segura, J, 1996)	0.29
" In the studies reported in this paper it is demonstrated that both MelIQx and PhIP are well absorbed and extensively metabolized following ingestion of amine-containing beef by humans."	( Systemic exposure to dietary heterocyclic amines in man. Boobis, AR; Davies, DS; de la Torre, R; Gooderham, NJ; Lynch, A; Murray, S; Segura, J, 1995)	0.29
" The aim of this study was to examine the bioavailability of these compounds to human breast tissue and their ability to bind to DNA to form DNA adducts."	( Analysis of DNA adducts by accelerator mass spectrometry in human breast tissue after administration of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine and benzo[a]pyrene. Coxhead, JM; Cupid, BC; Garner, RC; Lightfoot, TJ; Nicholson, S, 2000)	0.31
" In accordance, BSO treatment increased oral bioavailability in intact Wistar rats."	( Increased bioavailability of the food-derived carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in MRP2-deficient rats. de Waart, DR; Dietrich, CG; Elferink, RP; Ottenhoff, R; Schoots, IG, 2001)	0.31
" These data suggest that the transport of AFB(1) and DBP can be inhibited by CHL, which supports a model of direct binding in the intestinal tract of CHL to these carcinogens with resultant reduction of bioavailability as one mechanism of action as a cancer chemopreventive agent."	( Effects of chlorophyllin on transport of dibenzo(a, l)pyrene, 2-amino-1-methyl-6-phenylimidazo-[4,5-b]pyridine, and aflatoxin B(1) across Caco-2 cell monolayers. Gray, JE; Mata, JE; Rodriguez-Proteau, R; Williams, DE; Yu, Z, 2004)	0.32
" Selective down-regulation during cholestasis might be the consequence of species-specific transcriptional and posttranscriptional mechanisms and contributes to higher bioavailability of a food-derived carcinogen."	( Consequences of bile duct obstruction on intestinal expression and function of multidrug resistance-associated protein 2. Dietrich, CG; Gartung, C; Geier, A; Lammert, F; Matern, S; Oude Elferink, RP; Roeb, E; Salein, N, 2004)	0.32
" This points to flavonoid-mediated stimulation of the bioavailability of PhIP and, thus, a possible adverse effect of these supposed beneficial food ingredients."	( An in vitro and in silico study on the flavonoid-mediated modulation of the transport of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) through Caco-2 monolayers. Alink, GM; Freidig, AP; Groten, JP; Rietjens, IM; Schutte, ME; van de Sandt, JJ, 2006)	0.33
" This flavonoid-mediated increase in PhIP transport through Caco-2 monolayers may point at a possible increased bioavailability of PhIP in the presence of flavonoid mixtures in the in vivo situation."	( Effects of flavonoid mixtures on the transport of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) through Caco-2 monolayers: an in vitro and kinetic modeling approach to predict the combined effects on transporter inhibition. Boersma, MG; Groten, JP; Rietjens, IM; Schutte, ME; Verhallen, DA, 2008)	0.35
" It is concluded that quercetin increases the bioavailability of the pro-carcinogen PhIP in rats pointing at a potential adverse effect of this supposed beneficial food ingredient."	( Quercetin increases the bioavailability of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in rats. Alink, GM; Freidig, AP; Groten, JP; Rietjens, IM; Schutte, ME; Spenkelink, B; Vaessen, JC; van de Sandt, JJ, 2008)	0.35
" These findings signify that the exposure and bioavailability of PhIP are high in canines."	( Biomonitoring the cooked meat carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in canine fur. Gu, D; Modiano, JF; Neuman, ZL; Turesky, RJ, 2012)	0.38
" The intestinal absorption of PHIP-M1 is comparable with that of PHIP and a moderate to high bioavailability has to be expected."	( Development of an online-SPE-LC-MS method for the investigation of the intestinal absorption of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PHIP) and its bacterial metabolite PHIP-M1 in a Caco-2 Transwell system. Schebb, NH; Steinberg, P; von Elsner, L; Willenberg, I, 2015)	0.42
" In the present study, we applied the Caco-2-transwell-system in order to investigate the modulation of intestinal bioavailability by soluble fibers."	( Investigation of the effects of soluble fibers on the absorption of resveratrol and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PHIP) in the Caco-2 cellular model of intestinal absorption. Schebb, NH; Willenberg, I; Wonik, J, 2015)	0.42

Excerpt	Relevance	Reference
" HPLC separation followed by liquid scintillation counting of hydrolyzed liver DNA from a rat dosed with [3H]PhIP showed that radioactivity coeluted with the hydrolysis product of the synthetic PhIP-2-deoxyguanosine adduct, indicating that PhIP in vivo also forms an N2-(2'-deoxyguanosin-8-yl)-PhIP adduct."	( Reaction of the N2-acetoxy derivative of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) with 2'-deoxyguanosine and DNA. Synthesis and identification of N2-(2'-deoxyguanosin-8-yl)-PhIP. Andersson, R; Dragsted, L; Frandsen, H; Grivas, S; Larsen, JC, 1992)	0.28
" Significantly higher levels of labelled compounds could be detected in the blood of animals dosed ip than in that of those dosed by gavage at 6 and 12 hr after dosing."	( The metabolic disposition of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in the induced mouse. Felton, JS; Healy, SK; Knize, MG; Tucker, JD; Turteltaub, KW, 1989)	0.28
" Urine samples and faecal extracts from 3H-PhIP or 2-14C-DiMeIQx dosed rats were analysed by these ELISA assays, and high correlations between radioactivity and response in the ELISA assays were observed."	( Antibodies to the food mutagens, 2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine and 2-amino-3,4,8-trimethylimidazo[4,5-f]quinoxaline: useful for immunoassay and immunoaffinity chromatography of biological samples. Dragsted, LO; Frandsen, H; Grivas, S; Larsen, JC, 1995)	0.29
" 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
" Animals were killed 1, 2, 6, 12, 16 or 20 days after dosing (4 animals/time point) and their liver, lungs, stomach, small intestine, cecum, colon, kidneys, WBC, heart and spleen were removed for isolation of DNA and assay of PhIP-DNA adducts by 32P-postlabeling."	( Removal of DNA adducts of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in the male Fischer-344 rat. Cummings, DA; Schut, HA, 1994)	0.29
"In these studies, the food promutagen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) was evaluated for its immunotoxicity in B6C3F1 mice following oral 5-day dosing at total doses of 50 and 150 mg/kg."	( Inhibition of humoral immunity and mitogen responsiveness of lymphoid cells following oral administration of the heterocyclic food mutagen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) to B6C3F1 mice. Archuleta, MM; Born, JL; Burchiel, SW; Davis, DA; Felton, JS; Knize, MG, 1994)	0.29
" Adducts in white blood cell DNA increased with daily dosing for 9 days."	( DNA adduct levels of 2-amino-1-methyl-6-phenylimidazo-[4,5-b]pyridine (PhIP) in tissues of cynomolgus monkeys after single or multiple dosing. Adamson, RH; Nagao, M; Schut, HA; Snyderwine, EG; Sugimura, T, 1994)	0.29
" HPLC analysis of stomach contents and tissues of newborn mice exposed for 4 hr to lactating dams dosed ip with [3H]PhIP (5."	( Transfer of the food mutagen PhIP to foetuses and newborn mice following maternal exposure. Brittebo, EB; Jägerstad, IM; Karlsson, AA; Skog, KI, 1994)	0.29
" DNA adducts from hepatocytes dosed with N-hydroxy-PhIP, however, resulted in a decrease in adduct levels from cells pretreated with PCP or DCNP."	( The role of sulfation and/or acetylation in the metabolism of the cooked-food mutagen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in Salmonella typhimurium and isolated rat hepatocytes. Buonarati, MH; Felton, JS; Malfatti, MA; Shen, NH; Turteltaub, KW, )	0.13
" Incubations of 3-methylcholanthrene-induced colon slices dosed with 50 microMolar [(3)H]PhIP produced no detectable metabolites."	( The capability of rat colon tissue slices to metabolize the cooked-food carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine. Connors, MS; Felton, JS; Malfatti, MA; Mauthe, RJ, 1996)	0.29
" The results indicate that unconjugated N-OH-PhIP is not excreted in the urine after oral dosing with PhIP and that the two isomeric N-glucuronides of N-OH-PhIP, which are formed as major metabolites, are stable under acidic conditions."	( Metabolic activation and DNA adduct detection of PhIP in dogs, rats, and humans in relation to urinary bladder and colon carcinogenesis. Bartsch, H; Butler, MA; Friesen, MD; Ilett, KF; Kaderlik, RK; Kadlubar, F; Lin, D; Minchin, RF; Mulder, GJ; Teitel, CH, 1995)	0.29
"The carcinogenic potential of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), identified as the most abundant mutagenic heterocyclic amine in cooked meat and fish, was investigated in dose-response studies."	( Carcinogenicity of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in rats: dose-response studies. Hasegawa, R; Ito, N; Masui, T; Sano, M; Shirai, T; Tamano, S, 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
" HPLC analysis of samples of urine and extracts from faeces, from rats dosed with [3H]PhIP-dG, showed that approximately 90% of the radioactivity co-eluted with PhIP-dG, indicating that PhIP-dG is excreted unmetabolized."	( Excretion of DNA adducts of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine and 2-amino-3,4,8-trimethylimidazo[4,5-f]quinoxaline, PhIP-dG, PhIP-DNA and DiMeIQx-DNA from the rat. Frandsen, H, 1997)	0.3
" The current experimental data demonstrate that only a 20-week period of PhIP treatment is sufficient for induction of ventral carcinomas and that long-term pharmacological dosing with testosterone propionate which applied through a Silastic tube embedded in the subcutis after PhIP treatment can induce invasive carcinomas in the anterior prostate and seminal vesicles."	( Carcinogenicity of 2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine (PhIP) in the rat prostate and induction of invasive carcinomas by subsequent treatment with testosterone propionate. Asamoto, M; Cui, L; Futakuchi, M; Ito, N; Kato, K; Shirai, T; Takahashi, S, 1999)	0.3
" At 20 weeks after the last dosing of PhIP, all animals were killed and complete autopsy was made."	( Chemopreventive effects of ONO-8711, a selective prostaglandin E receptor EP(1) antagonist, on breast cancer development. Kawamori, T; Kondo, K; Maruyama, T; Nakatsugi, S; Ohuchida, S; Sugimura, T; Uchiya, N; Wakabayashi, K; Watanabe, K; Yamamoto, H, 2001)	0.31
" These featured dietary administration of PhIP at different dose levels and for different durations, and included intragastric dosing for a short period, or continuous dietary administration after initiation with other carcinogen, namely 3,2'-dimethyl-4-aminobiphenyl (DMAB) or 1,2-dimethylhydrazine (DMH)."	( Organ differences in the enhancing potential of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine on carcinogenicity in the prostate, colon and pancreas. Asamoto, M; Futakuchi, M; Imaida, K; Kato, K; Shirai, T; Suzuki, S; Takahashi, S, 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
" CR itself caused significant induction of MN at dose levels > or =15 microg/ml; in combination experiments with B(a)P and PhIP, U-shaped dose-response curves were obtained and protection was found only in a narrow dose range (5 - 10 microg/ml)."	( Effect of chrysin, a flavonoid compound, on the mutagenic activity of 2-amino-1-methyl-6-phenylimidazo[4,5- b]pyridine (PhIP) and benzo(a)pyrene (B(a)P) in bacterial and human hepatoma (HepG2) cells. Chakraborty, A; Ecker, S; Kassie, F; Knasmüller, S; Lhoste, E; Mohn, G; Uhl, M, 2003)	0.32
" We detected significant dose-response relationship and correlation (r=0."	( Detection of 2-amino-1-methyl-6-phenylimidazo[4,5-b]-pyridine-DNA adducts in normal breast tissues and risk of breast cancer. Bondy, ML; Chang, P; Li, D; Sahin, AA; Shirai, T; Singletary, SE; Takahashi, S; Zhu, J, 2003)	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
" Urine was collected for 24 hours after dosing for metabolite analysis, and DNA was extracted from colon tissue and analyzed by accelerator mass spectrometry for DNA adducts."	( The urinary metabolite profile of the dietary carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine is predictive of colon DNA adducts after a low-dose exposure in humans. Dingley, KH; Felton, JS; Lang, NP; Malfatti, MA; Mulakken, N; Nelson, D; Nowell-Kadlubar, S; Turteltaub, KW; Ubick, EA, 2006)	0.33
" To distinguish between blocking and suppressing effects, and thus provide mechanistic insights into prevention during the initiation versus post-initiation phases of carcinogenesis, white tea, and green tea were administered at 2% (w/v) as the sole source of drinking fluid either 2 wk before and 2 wk during PhIP dosing (100 mg/kg, every other day by oral gavage), or starting 1 wk after the carcinogen and continued until the study was terminated at 16 wk."	( Comparison of white tea, green tea, epigallocatechin-3-gallate, and caffeine as inhibitors of PhIP-induced colonic aberrant crypts. Bailey, GS; Carter, O; Dashwood, RH; Dashwood, WM; Fischer, KA; Löhr, CV; Orner, GA; Pereira, CB; Wang, R; Williams, DE, 2007)	0.34
" PhIP/HF dosing caused a significant increase in the bromodeoxyuridine labeling index throughout the entire colon, and within the colonic crypt column cleaved caspase-3 was elevated in the basal and central zones, but reduced in the luminal region."	( beta-catenin is strongly elevated in rat colonic epithelium following short-term intermittent treatment with 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) and a high-fat diet. Dashwood, RH; Dashwood, WM; Fischer, KA; Löhr, CV; Nakagama, H; Wang, R; Williams, DE, 2008)	0.35
"45 micromol PhIP/kg bw and 30 micromol quercetin/kg bw significantly increased the blood AUC(0-8h) of PhIP in rats to 131+/-14% of the AUC(0-8h) for rats dosed with PhIP alone."	( Quercetin increases the bioavailability of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in rats. Alink, GM; Freidig, AP; Groten, JP; Rietjens, IM; Schutte, ME; Spenkelink, B; Vaessen, JC; van de Sandt, JJ, 2008)	0.35
" 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
"The animal feeding study of PhIP found a significant dose-response relationship between dosage and PhIP in rat fur."	( Validity of a self-administered food frequency questionnaire in the estimation of heterocyclic aromatic amines. Ishihara, J; Iwasaki, M; Mukai, T; Takachi, R; Totsuka, Y; Tsugane, S, 2014)	0.4
" In addition, we assessed a dose-response relationship."	( Dietary Heterocyclic Amine Intake and Colorectal Adenoma Risk: A Systematic Review and Meta-analysis. Castaño, PR; Linseisen, J; Martínez Góngora, V; Matthes, KL; Rohrmann, S, 2019)	0.51
" Furthermore, we observed a significant dose-response effect for PhIP, MeIQx, and mutagenicity index."	( Dietary Heterocyclic Amine Intake and Colorectal Adenoma Risk: A Systematic Review and Meta-analysis. Castaño, PR; Linseisen, J; Martínez Góngora, V; Matthes, KL; Rohrmann, S, 2019)	0.51
" In addition, our dose-response analyses showed an increased risk of CRA for PhIP, MeIQx, and mutagenicity index."	( Dietary Heterocyclic Amine Intake and Colorectal Adenoma Risk: A Systematic Review and Meta-analysis. Castaño, PR; Linseisen, J; Martínez Góngora, V; Matthes, KL; Rohrmann, S, 2019)	0.51

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.
mutagen	An agent that increases the frequency of mutations above the normal background level, usually by interacting directly with DNA and causing it damage, including base substitution.
[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
imidazopyridine
primary amino compound	A compound formally derived from ammonia by replacing one hydrogen atom by an organyl group.
[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]

Assay ID	Title	Year	Journal	Article
AID681275	TP_TRANSPORTER: transcellular transport in MDCKII	2003	Cancer research, Oct-01, Volume: 63, Issue:19	The breast cancer resistance protein (Bcrp1/Abcg2) restricts exposure to the dietary carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine.
AID497849	Inhibition of NF-kappaB expressed in human MCF7 cells assessed as inhibition of TNF-alpha-induced IL6 mRNA expression by RT-PCR	2008	Nature chemical biology, Apr, Volume: 4, Issue:4	NFkappaB selectivity of estrogen receptor ligands revealed by comparative crystallographic analyses.
AID681448	TP_TRANSPORTER: biliary excretion	2003	Cancer research, Oct-01, Volume: 63, Issue:19	The breast cancer resistance protein (Bcrp1/Abcg2) restricts exposure to the dietary carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine.
AID497848	Inhibition of NF-kappaB expressed in human MCF7 cells assessed as inhibition of TNF-alpha-induced MCP1 mRNA expression by RT-PCR	2008	Nature chemical biology, Apr, Volume: 4, Issue:4	NFkappaB selectivity of estrogen receptor ligands revealed by comparative crystallographic analyses.
AID680783	TP_TRANSPORTER: transepithelial transport (basal to apical) in MRP2-expressing MDCKII cells	2001	Molecular pharmacology, May, Volume: 59, Issue:5	Increased bioavailability of the food-derived carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in MRP2-deficient rats.
AID497850	Inhibition of NF-kappaB expressed in human MCF7 cells assessed as inhibition of TNF-alpha-induced IL8 mRNA expression by RT-PCR	2008	Nature chemical biology, Apr, Volume: 4, Issue:4	NFkappaB selectivity of estrogen receptor ligands revealed by comparative crystallographic analyses.
AID497847	Inhibition of NF-kappaB expressed in human MCF7 cells assessed as inhibition of TNF-alpha-induced transcriptional activity by luciferase reporter gene assay	2008	Nature chemical biology, Apr, Volume: 4, Issue:4	NFkappaB selectivity of estrogen receptor ligands revealed by comparative crystallographic analyses.
AID497846	Activity at estrogen receptor expressed in human MCF7 cells assessed as increase in receptor-mediated transcription by ERE-luciferase reporter gene assay relative to estradiol	2008	Nature chemical biology, Apr, Volume: 4, Issue:4	NFkappaB selectivity of estrogen receptor ligands revealed by comparative crystallographic analyses.
AID682139	TP_TRANSPORTER: intestinal excretion	2003	Cancer research, Oct-01, Volume: 63, Issue:19	The breast cancer resistance protein (Bcrp1/Abcg2) restricts exposure to the dietary carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	12 (1.44)	18.7374
1990's	313 (37.49)	18.2507
2000's	310 (37.13)	29.6817
2010's	161 (19.28)	24.3611
2020's	39 (4.67)	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	6 (0.70%)	5.53%
Reviews	49 (5.72%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	801 (93.57%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
dinitrochlorobenzene Dinitrochlorobenzene: A skin irritant that may cause dermatitis of both primary and allergic types. Contact sensitization with DNCB has been used as a measure of cellular immunity. DNCB is also used as a reagent for the detection and determination of pyridine compounds.. 1-chloro-2,4-dinitrobenzene : A C-nitro compound that is chlorobenzene carrying a nitro substituent at each of the 2- and 4-positions.	2	1	0	C-nitro compound; monochlorobenzenes	allergen; epitope; sensitiser
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.	2.46	2	0	catechols; dihydroxybenzoic acid	antineoplastic agent; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor; human xenobiotic metabolite; plant metabolite
acetaldehyde Acetaldehyde: A colorless, flammable liquid used in the manufacture of acetic acid, perfumes, and flavors. It is also an intermediate in the metabolism of alcohol. It has a general narcotic action and also causes irritation of mucous membranes. Large doses may cause death from respiratory paralysis.. acetaldehyde : The aldehyde formed from acetic acid by reduction of the carboxy group. It is the most abundant carcinogen in tobacco smoke.. aldehyde : A compound RC(=O)H, in which a carbonyl group is bonded to one hydrogen atom and to one R group.. acetyl group : A group, formally derived from acetic acid by dehydroxylation, which is fundamental to the biochemistry of all forms of life. When bound to coenzyme A, it is central to the metabolism of carbohydrates and fats.	3.96	12	0	aldehyde	carcinogenic agent; EC 3.5.1.4 (amidase) inhibitor; electron acceptor; Escherichia coli metabolite; human metabolite; mouse metabolite; mutagen; oxidising agent; Saccharomyces cerevisiae metabolite; teratogenic agent
ammonium hydroxide azane : Saturated acyclic nitrogen hydrides having the general formula NnHn+2.	2.1	1	0	azane; gas molecular entity; mononuclear parent hydride	EC 3.5.1.4 (amidase) inhibitor; metabolite; mouse metabolite; neurotoxin; NMR chemical shift reference compound; nucleophilic reagent; refrigerant
1-butanol 1-Butanol: A four carbon linear hydrocarbon that has a hydroxy group at position 1.. butan-1-ol : A primary alcohol that is butane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It it produced in small amounts in humans by the gut microbes.	1.99	1	0	alkyl alcohol; primary alcohol; short-chain primary fatty alcohol	human metabolite; mouse metabolite; protic solvent
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	0	monocarboxylic acid	antibacterial agent; astringent; metabolite; protic solvent; solvent
hydrochloric acid Hydrochloric Acid: A strong corrosive acid that is commonly used as a laboratory reagent. It is formed by dissolving hydrogen chloride in water. GASTRIC ACID is the hydrochloric acid component of GASTRIC JUICE.. hydrogen chloride : A mononuclear parent hydride consisting of covalently bonded hydrogen and chlorine atoms.	2.04	1	0	chlorine molecular entity; gas molecular entity; hydrogen halide; mononuclear parent hydride	mouse metabolite
coumarin 2H-chromen-2-one: coumarin derivative	1.99	1	0	coumarins	fluorescent dye; human metabolite; plant metabolite
gallic acid gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.	2.39	2	0	trihydroxybenzoic acid	antineoplastic agent; antioxidant; apoptosis inducer; astringent; cyclooxygenase 2 inhibitor; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; geroprotector; human xenobiotic metabolite; plant metabolite
creatine [no description available]	4.8	7	1	glycine derivative; guanidines; zwitterion	geroprotector; human metabolite; mouse metabolite; neuroprotective agent; nutraceutical
formaldehyde paraform: polymerized formaldehyde; RN given refers to parent cpd; used in root canal therapy	2.73	3	0	aldehyde; one-carbon compound	allergen; carcinogenic agent; disinfectant; EC 3.5.1.4 (amidase) inhibitor; environmental contaminant; Escherichia coli metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
glyceraldehyde Glyceraldehyde: An aldotriose containing the propionaldehyde structure with hydroxy groups at the 2- and 3-positions. It is involved in the formation of ADVANCED GLYCOSYLATION END PRODUCTS.. glyceraldehyde : An aldotriose comprising propanal having hydroxy groups at the 2- and 3-positions. It plays role in the formation of advanced glycation end-products (AGEs), a deleterious accompaniment to ageing.. aldose : Aldehydic parent sugars (polyhydroxy aldehydes H[CH(OH)]nC(=O)H, n >= 2) and their intramolecular hemiacetals.	2.13	1	0	aldotriose	fundamental metabolite
glycerol Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.	2.79	3	0	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
histamine [no description available]	2.31	1	0	aralkylamino compound; imidazoles	human metabolite; mouse metabolite; neurotransmitter
indole [no description available]	2.21	1	0	indole; polycyclic heteroarene	Escherichia coli metabolite
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.	2.66	2	0	2-oxo aldehyde; propanals	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
melatonin [no description available]	3.57	2	0	acetamides; tryptamines	anticonvulsant; central nervous system depressant; geroprotector; hormone; human metabolite; immunological adjuvant; mouse metabolite; radical scavenger
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	2.08	1	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
nitrites Nitrites: Salts of nitrous acid or compounds containing the group NO2-. The inorganic nitrites of the type MNO2 (where M=metal) are all insoluble, except the alkali nitrites. The organic nitrites may be isomeric, but not identical with the corresponding nitro compounds. (Grant & Hackh's Chemical Dictionary, 5th ed)	2.08	1	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species	human metabolite
palmitic acid Palmitic Acid: A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids.. hexadecanoic acid : A straight-chain, sixteen-carbon, saturated long-chain fatty acid.	2.6	1	0	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; EC 1.1.1.189 (prostaglandin-E2 9-reductase) inhibitor; plant metabolite
pentachlorophenol PENTA: structure given in first source	2.39	2	0	aromatic fungicide; chlorophenol; organochlorine pesticide; pentachlorobenzenes	human xenobiotic metabolite
phenylacetaldehyde [no description available]	3.91	11	0	alpha-CH2-containing aldehyde; phenylacetaldehydes	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
pyridine azine : An organonitrogen compound of general structure RCH=N-N=CHR or RR'C=N-N=CRR'.	3.09	4	0	azaarene; mancude organic heteromonocyclic parent; monocyclic heteroarene; pyridines	environmental contaminant; NMR chemical shift reference compound
sulfites Sulfites: Inorganic salts of sulfurous acid.. sulfites : Any sulfurous acid derivative that is a salt or an ester of sulfurous acid.. organosulfonate oxoanion : An organic anion obtained by deprotonation of the sufonate group(s) of any organosulfonic acid.. sulfite : A sulfur oxoanion that is the conjugate base of hydrogen sulfite (H2SO3).	2.4	2	0	divalent inorganic anion; sulfur oxide; sulfur oxoanion
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	0	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.	3.39	7	0	hydrazines	alkylating agent; carcinogenic agent
2-aminofluorene [no description available]	2.69	3	0
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.	3.07	5	0	ortho- and peri-fused polycyclic arene	aryl hydrocarbon receptor agonist; carcinogenic agent
theophylline [no description available]	5.58	5	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.	3.57	2	0	pyrazolone	antipyretic; cyclooxygenase 3 inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
arecoline Arecoline: An alkaloid obtained from the betel nut (Areca catechu), fruit of a palm tree. It is an agonist at both muscarinic and nicotinic acetylcholine receptors. It is used in the form of various salts as a ganglionic stimulant, a parasympathomimetic, and a vermifuge, especially in veterinary practice. It has been used as a euphoriant in the Pacific Islands.. arecoline : A tetrahydropyridine that is 1,2,5,6-tetrahydropyridine with a methyl group at position 1, and a methoxycarbonyl group at position 3. An alkaloid found in the areca nut, it acts as an agonist of muscarinic acetylcholine.	3.15	1	0	enoate ester; methyl ester; pyridine alkaloid; tetrahydropyridine	metabolite; muscarinic agonist
aspirin Aspirin: The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5). acetylsalicylate : A benzoate that is the conjugate base of acetylsalicylic acid, arising from deprotonation of the carboxy group.. acetylsalicylic acid : A member of the class of benzoic acids that is salicylic acid in which the hydrogen that is attached to the phenolic hydroxy group has been replaced by an acetoxy group. A non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity.	2.68	3	0	benzoic acids; phenyl acetates; salicylates	anticoagulant; antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; EC 1.1.1.188 (prostaglandin-F synthase) inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; plant activator; platelet aggregation inhibitor; prostaglandin antagonist; teratogenic agent
benzo(a)pyrene Benzo(a)pyrene: A potent mutagen and carcinogen. It is a public health concern because of its possible effects on industrial workers, as an environmental pollutant, an as a component of tobacco smoke.. benzo[a]pyrene : An ortho- and peri-fused polycyclic arene consisting of five fused benzene rings.	9.25	38	1	ortho- and peri-fused polycyclic arene	carcinogenic agent; mouse metabolite
benzyl isothiocyanate benzyl isothiocyanate: inhibits carcinogen-induced neoplasia; structure in Negwer, 5th ed, #715; also promotes urinary bladder carcinoma	2.41	2	0	benzenes; isothiocyanate	antibacterial drug
beta-naphthoflavone beta-Naphthoflavone: A polyaromatic hydrocarbon inducer of P4501A1 and P4501A2 cytochromes. (Proc Soc Exp Biol Med 1994 Dec:207(3):302-308). beta-naphthoflavone : An extended flavonoid resulting from the formal fusion of a benzene ring with the f side of flavone.	3.38	7	0	extended flavonoid; naphtho-gamma-pyrone; organic heterotricyclic compound	aryl hydrocarbon receptor agonist
caffeine [no description available]	3.51	8	0	purine alkaloid; trimethylxanthine	adenosine A2A receptor antagonist; adenosine receptor antagonist; adjuvant; central nervous system stimulant; diuretic; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; environmental contaminant; food additive; fungal metabolite; geroprotector; human blood serum metabolite; mouse metabolite; mutagen; plant metabolite; psychotropic drug; ryanodine receptor agonist; xenobiotic
verapamil Verapamil: A calcium channel blocker that is a class IV anti-arrhythmia agent.. verapamil : A racemate comprising equimolar amounts of dexverapamil and (S)-verapamil. An L-type calcium channel blocker of the phenylalkylamine class, it is used (particularly as the hydrochloride salt) in the treatment of hypertension, angina pectoris and cardiac arrhythmia, and as a preventive medication for migraine.. 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile : A tertiary amino compound that is 3,4-dimethoxyphenylethylamine in which the hydrogens attached to the nitrogen are replaced by a methyl group and a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.	2	1	0	aromatic ether; nitrile; polyether; tertiary amino compound
camphor, (+-)-isomer [no description available]	1.97	1	0	bornane monoterpenoid; cyclic monoterpene ketone	plant metabolite
cimetidine Cimetidine: A histamine congener, it competitively inhibits HISTAMINE binding to HISTAMINE H2 RECEPTORS. Cimetidine has a range of pharmacological actions. It inhibits GASTRIC ACID secretion, as well as PEPSIN and GASTRIN output.. cimetidine : A member of the class of guanidines that consists of guanidine carrying a methyl substituent at position 1, a cyano group at position 2 and a 2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl group at position 3. It is a H2-receptor antagonist that inhibits the production of acid in stomach.	7.02	1	0	aliphatic sulfide; guanidines; imidazoles; nitrile	adjuvant; analgesic; anti-ulcer drug; H2-receptor antagonist; P450 inhibitor
dantrolene Dantrolene: Skeletal muscle relaxant that acts by interfering with excitation-contraction coupling in the muscle fiber. It is used in spasticity and other neuromuscular abnormalities. Although the mechanism of action is probably not central, dantrolene is usually grouped with the central muscle relaxants.. dantrolene : The hydrazone resulting from the formal condensation of 5-(4-nitrophenyl)furfural with 1-aminohydantoin. A ryanodine receptor antagonist used for the relief of chronic severe spasticity and malignant hyperthermia.	2.04	1	0	hydrazone; imidazolidine-2,4-dione	muscle relaxant; neuroprotective agent; ryanodine receptor antagonist
debrisoquin Debrisoquin: An adrenergic neuron-blocking drug similar in effects to GUANETHIDINE. It is also noteworthy in being a substrate for a polymorphic cytochrome P-450 enzyme. Persons with certain isoforms of this enzyme are unable to properly metabolize this and many other clinically important drugs. They are commonly referred to as having a debrisoquin 4-hydroxylase polymorphism.	1.97	1	0	carboxamidine; isoquinolines	adrenergic agent; antihypertensive agent; human metabolite; sympatholytic agent
eflornithine Eflornithine: An inhibitor of ORNITHINE DECARBOXYLASE, the rate limiting enzyme of the polyamine biosynthetic pathway.. eflornithine : A fluoroamino acid that is ornithine substituted by a difluoromethyl group at position 2.	2.4	2	0	alpha-amino acid; fluoroamino acid	trypanocidal drug
dipyridamole Dipyridamole: A phosphodiesterase inhibitor that blocks uptake and metabolism of adenosine by erythrocytes and vascular endothelial cells. Dipyridamole also potentiates the antiaggregating action of prostacyclin. (From AMA Drug Evaluations Annual, 1994, p752). dipyridamole : A pyrimidopyrimidine that is 2,2',2'',2'''-(pyrimido[5,4-d]pyrimidine-2,6-diyldinitrilo)tetraethanol substituted by piperidin-1-yl groups at positions 4 and 8 respectively. A vasodilator agent, it inhibits the formation of blood clots.	2.1	1	0	piperidines; pyrimidopyrimidine; tertiary amino compound; tetrol	adenosine phosphodiesterase inhibitor; EC 3.5.4.4 (adenosine deaminase) inhibitor; platelet aggregation inhibitor; vasodilator agent
furafylline [no description available]	5.58	5	1	oxopurine
ethidium Ethidium: A trypanocidal agent and possible antiviral agent that is widely used in experimental cell biology and biochemistry. Ethidium has several experimentally useful properties including binding to nucleic acids, noncompetitive inhibition of nicotinic acetylcholine receptors, and fluorescence among others. It is most commonly used as the bromide.. ethidium : The fluorescent compound widely used in experimental cell biology and biochemistry to reveal double-stranded DNA and RNA.	1.99	1	0	phenanthridines	fluorochrome; intercalator
hydroxyurea [no description available]	2.02	1	0	one-carbon compound; ureas	antimetabolite; antimitotic; antineoplastic agent; DNA synthesis inhibitor; EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor; genotoxin; immunomodulator; radical scavenger; teratogenic agent
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.	3.61	9	0	indolyl alcohol	antineoplastic agent; plant metabolite
mimosine Mimosine: 3-Hydroxy-4-oxo-1(4H)-pyridinealanine. An antineoplastic alanine-substituted pyridine derivative isolated from Leucena glauca.	2.11	1	0	alpha-amino acid
lamotrigine [no description available]	2.11	1	0	1,2,4-triazines; dichlorobenzene; primary arylamine	anticonvulsant; antidepressant; antimanic drug; calcium channel blocker; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; environmental contaminant; excitatory amino acid antagonist; geroprotector; non-narcotic analgesic; xenobiotic
metformin Metformin: A biguanide hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. Metformin improves glycemic control by improving insulin sensitivity and decreasing intestinal absorption of glucose. (From Martindale, The Extra Pharmacopoeia, 30th ed, p289). metformin : A member of the class of guanidines that is biguanide the carrying two methyl substituents at position 1.	2.66	2	0	guanidines	environmental contaminant; geroprotector; hypoglycemic agent; xenobiotic
methyl parathion Methyl Parathion: The methyl homolog of parathion. An effective, but highly toxic, organothiophosphate insecticide and cholinesterase inhibitor.. parathion-methyl : A C-nitro compound that is 4-nitrophenol substituted by a (dimethoxyphosphorothioyl)oxy group at position 4.	2.01	1	0	C-nitro compound; organic thiophosphate; organothiophosphate insecticide	acaricide; agrochemical; antifungal agent; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; environmental contaminant; genotoxin
mitoxantrone Mitoxantrone: An anthracenedione-derived antineoplastic agent.. mitoxantrone : A dihydroxyanthraquinone that is 1,4-dihydroxy-9,10-anthraquinone which is substituted by 6-hydroxy-1,4-diazahexyl groups at positions 5 and 8.	2.07	1	0	dihydroxyanthraquinone	analgesic; antineoplastic agent
nimesulide nimesulide: structure. nimesulide : An aromatic ether having phenyl and 2-methylsulfonamido-5-nitrophenyl as the two aryl groups.	2.41	2	0	aromatic ether; C-nitro compound; sulfonamide	cyclooxygenase 2 inhibitor; non-steroidal anti-inflammatory drug
pd 98059 2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one: inhibits MAP kinase kinase (MEK) activity, p42 MAPK and p44 MAPK; structure in first source. 2-(2-amino-3-methoxyphenyl)chromen-4-one : A member of the class of monomethoxyflavones that is 3'-methoxyflavone bearing an additional amino substituent at position 2'.	2.03	1	0	aromatic amine; monomethoxyflavone	EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector
phenacetin Saridon: contains phenacetin, caffeine, propyphenazone & pyrithyldione	3.37	1	1	acetamides; aromatic ether	cyclooxygenase 3 inhibitor; non-narcotic analgesic; peripheral nervous system drug
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.	2.67	3	0	barbiturates	anticonvulsant; drug allergen; excitatory amino acid antagonist; sedative
prazosin Prazosin: A selective adrenergic alpha-1 antagonist used in the treatment of HEART FAILURE; HYPERTENSION; PHEOCHROMOCYTOMA; RAYNAUD DISEASE; PROSTATIC HYPERTROPHY; and URINARY RETENTION.. prazosin : A member of the class of piperazines that is piperazine substituted by a furan-2-ylcarbonyl group and a 4-amino-6,7-dimethoxyquinazolin-2-yl group at positions 1 and 4 respectively.	2.04	1	0	aromatic ether; furans; monocarboxylic acid amide; piperazines; quinazolines	alpha-adrenergic antagonist; antihypertensive agent; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
safrole Safrole: A member of the BENZODIOXOLES that is a constituent of several VOLATILE OILS, notably SASSAFRAS oil. It is a precursor in the synthesis of the insecticide PIPERONYL BUTOXIDE and the drug N-methyl-3,4-methylenedioxyamphetamine (MDMA).. safrole : A member of the class of benzodioxoles that is 1,3-benzodioxole which is substituted by an allyl group at position 5. It is found in several plants, including black pepper, cinnamon and nutmeg, and is present in several essential oils, notably that of sassafras. It has insecticidal properties and has been used as a topical antiseptic. Although not thought to pose a significant carcinogenic risk to humans, findings of weak carcinogenicity in rats have resulted in the banning of its (previously widespread) use in perfumes and soaps, and as a food additive.	1.97	1	0	benzodioxoles	flavouring agent; insecticide; metabolite; plant metabolite
sulforaphane sulforaphane: from Cardaria draba L.. sulforaphane : An isothiocyanate having a 4-(methylsulfinyl)butyl group attached to the nitrogen.	2.48	2	0	isothiocyanate; sulfoxide	antineoplastic agent; antioxidant; EC 3.5.1.98 (histone deacetylase) inhibitor; plant metabolite
triamterene Triamterene: A pteridinetriamine compound that inhibits SODIUM reabsorption through SODIUM CHANNELS in renal EPITHELIAL CELLS.. triamterene : Pteridine substituted at positions 2, 4 and 7 with amino groups and at position 6 with a phenyl group. A sodium channel blocker, it is used as a diuretic in the treatment of hypertension and oedema.	2.04	1	0	pteridines	diuretic; sodium channel blocker
1,4-phenylenebis(methylene)selenocyanate 1,4-phenylenebis(methylene)selenocyanate: structure given in first source; inhibits DMBA-induced carcinogenesis by inhibiting DMBA-DNA adduct formation	2	1	0
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.	3.12	1	0	mitomycin	alkylating agent; antineoplastic agent
thymidine [no description available]	1.98	1	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite
aldosterone [no description available]	2.42	2	0	11beta-hydroxy steroid; 18-oxo steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid hormone; mineralocorticoid; primary alpha-hydroxy ketone; steroid aldehyde	human metabolite; mouse metabolite
n-hydroxy-2-aminofluorene N-hydroxy-2-aminofluorene: structure	1.98	1	0
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.	3.24	6	0	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.	2.38	2	0	nitrosamine	carcinogenic agent; hepatotoxic agent; mutagen
4-nitroquinoline-1-oxide 4-nitroquinoline N-oxide : A quinoline N-oxide carrying a nitro substituent at position 4.	2.53	2	0	C-nitro compound; quinoline N-oxide	carcinogenic agent
allyl isothiocyanate allyl isothiocyanate: used in the manufacture of flavors, war gases; medical use as a counterirritant; structure. allyl isothiocyanate : An isothiocyanate with the formula CH2=CHCH2N=C=S. A colorless oil with boiling point 152degreeC, it is responsible for the pungent taste of mustard, horseradish, and wasabi.	2.41	1	0	alkenyl isothiocyanate; isothiocyanate	antimicrobial agent; antineoplastic agent; apoptosis inducer; lachrymator; metabolite
ethinyl estradiol Ethinyl Estradiol: A semisynthetic alkylated ESTRADIOL with a 17-alpha-ethinyl substitution. It has high estrogenic potency when administered orally, and is often used as the estrogenic component in ORAL CONTRACEPTIVES.. 17alpha-ethynylestradiol : A 3-hydroxy steroid that is estradiol substituted by a ethynyl group at position 17. It is a xenoestrogen synthesized from estradiol and has been shown to exhibit high estrogenic potency on oral administration.	2.01	1	0	17-hydroxy steroid; 3-hydroxy steroid; terminal acetylenic compound	xenoestrogen
9,10-dimethyl-1,2-benzanthracene 9,10-Dimethyl-1,2-benzanthracene: Polycyclic aromatic hydrocarbon found in tobacco smoke that is a potent carcinogen.. 7,12-dimethyltetraphene : A tetraphene having methyl substituents at the 7- and 12-positions. It is a potent carcinogen and is present in tobacco smoke.	5.48	12	0	ortho-fused polycyclic arene; tetraphenes	carcinogenic agent
uridine diphosphate Uridine Diphosphate: A uracil nucleotide containing a pyrophosphate group esterified to C5 of the sugar moiety.	2.6	1	0	pyrimidine ribonucleoside 5'-diphosphate; uridine 5'-phosphate	Escherichia coli metabolite; mouse metabolite
bromodeoxyuridine Bromodeoxyuridine: A nucleoside that substitutes for thymidine in DNA and thus acts as an antimetabolite. It causes breaks in chromosomes and has been proposed as an antiviral and antineoplastic agent. It has been given orphan drug status for use in the treatment of primary brain tumors.	2.01	1	0	pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent
p-aminoazobenzene p-Aminoazobenzene: Used in the form of its salts as a dye and as an intermediate in manufacture of Acid Yellow, diazo dyes, and indulines.. 4-(phenylazo)aniline : Azobenzene substituted at one of the 4-positions by an amino group. It has a role as a dye and an allergen.	1.99	1	0
tyrosine Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.	2.97	4	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; proteinogenic amino acid; tyrosine	EC 1.3.1.43 (arogenate dehydrogenase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
phlorhizin [no description available]	2.13	1	0	aryl beta-D-glucoside; dihydrochalcones; monosaccharide derivative	antioxidant; plant metabolite
methylene blue Methylene Blue: A compound consisting of dark green crystals or crystalline powder, having a bronze-like luster. Solutions in water or alcohol have a deep blue color. Methylene blue is used as a bacteriologic stain and as an indicator. It inhibits GUANYLATE CYCLASE, and has been used to treat cyanide poisoning and to lower levels of METHEMOGLOBIN.. methylene blue : An organic chloride salt having 3,7-bis(dimethylamino)phenothiazin-5-ium as the counterion. A commonly used dye that also exhibits antioxidant, antimalarial, antidepressant and cardioprotective properties.	2.02	1	0	organic chloride salt	acid-base indicator; antidepressant; antimalarial; antimicrobial agent; antioxidant; cardioprotective agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 4.6.1.2 (guanylate cyclase) inhibitor; fluorochrome; histological dye; neuroprotective agent; physical tracer
aniline [no description available]	1.99	1	0	anilines; primary arylamine
dimethylnitrosamine Dimethylnitrosamine: A nitrosamine derivative with alkylating, carcinogenic, and mutagenic properties. It causes serious liver damage and is a hepatocarcinogen in rodents.	3.62	9	0	nitrosamine	geroprotector; mutagen
phenylalanine Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.	4.74	11	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; phenylalanine; proteinogenic amino acid	algal metabolite; EC 3.1.3.1 (alkaline phosphatase) inhibitor; Escherichia coli metabolite; human xenobiotic metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
colchicine (S)-colchicine : A colchicine that has (S)-configuration. It is a secondary metabolite, has anti-inflammatory properties and is used to treat gout, crystal-induced joint inflammation, familial Mediterranean fever, and many other conditions.	2.02	1	0	alkaloid; colchicine	anti-inflammatory agent; gout suppressant; mutagen
cytarabine [no description available]	2.02	1	0	beta-D-arabinoside; monosaccharide derivative; pyrimidine nucleoside	antimetabolite; antineoplastic agent; antiviral agent; immunosuppressive agent
histidine Histidine: An essential amino acid that is required for the production of HISTAMINE.. L-histidine : The L-enantiomer of the amino acid histidine.. histidine : An alpha-amino acid that is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3.	2.42	2	0	amino acid zwitterion; histidine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
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.	2.54	2	0	erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; tryptophan zwitterion; tryptophan	antidepressant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
boranes Boranes: The collective name for the boron hydrides, which are analogous to the alkanes and silanes. Numerous boranes are known. Some have high calorific values and are used in high-energy fuels. (From Grant & Hackh's Chemical Dictionary, 5th ed). borane : The simplest borane, consisting of a single boron atom carrying three hydrogens.. boranes : The molecular hydrides of boron.	2.13	1	0	boranes; mononuclear parent hydride
propane Propane: A three carbon alkane with the formula H3CCH2CH3.	2.44	2	0	alkane; gas molecular entity	food propellant
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.	2.44	2	0	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
tert-butylhydroperoxide tert-Butylhydroperoxide: A direct-acting oxidative stress-inducing agent used to examine the effects of oxidant stress on Ca(2+)-dependent signal transduction in vascular endothelial cells. It is also used as a catalyst in polymerization reactions and to introduce peroxy groups into organic molecules.. tert-butyl hydroperoxide : An alkyl hydroperoxide in which the alkyl group is tert-butyl. It is widely used in a variety of oxidation processes.	2.06	1	0	alkyl hydroperoxide	antibacterial agent; oxidising agent
acrylamide [no description available]	3.17	5	0	acrylamides; N-acylammonia; primary carboxamide	alkylating agent; carcinogenic agent; Maillard reaction product; mutagen; neurotoxin
quinoxalines quinoxaline : A naphthyridine in which the nitrogens are at positions 1 and 4.	13.04	159	3	mancude organic heterobicyclic parent; naphthyridine; ortho-fused heteroarene
quinoline [no description available]	2.31	1	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinolines
4-biphenylamine 4-biphenylamine: used in detection of sulfates, & as a carcinogen in cancer research; RN given refers to parent cpd; structure. biphenyl-4-amine : An aminobiphenyl that is biphenyl substituted by an amino group at position 4.	3.71	10	0	aminobiphenyl	carcinogenic agent
4-butyrolactone 4-Butyrolactone: One of the FURANS with a carbonyl thereby forming a cyclic lactone. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent.. tetrahydrofuranone : Any oxolane having an oxo- substituent at any position on the tetrahydrofuran ring.. gamma-butyrolactone : A butan-4-olide that is tetrahydrofuran substituted by an oxo group at position 2.	2.01	1	0	butan-4-olide	metabolite; neurotoxin
furaldehyde Furaldehyde: A heterocyclic compound consisting of a furan where the hydrogen at position 2 is substituted by a formyl group.. furfural : An aldehyde that is furan with the hydrogen at position 2 substituted by a formyl group.	2.49	2	0	aldehyde; furans	Maillard reaction product; metabolite
methyl gallate methyl gallate: has both immunosuppressive and phytogenic antineoplastic activities; isolated from Acer saccharinum. methyl 3,4,5-trihydroxybenzoate : A gallate ester obtained by the formal condensation of gallic acid with methanol. It exhibits anti-oxidant, anti-tumor, anti-microbial and anti-inflammatory properties.	1.99	1	0	gallate ester	anti-inflammatory agent; antioxidant; plant metabolite
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.	2.4	2	0	nitrosamine; piperidine	apoptosis inducer; carcinogenic agent; environmental contaminant; mutagen
acrolein [no description available]	1.99	1	0	enal	herbicide; human xenobiotic metabolite; toxin
glyoxal [no description available]	2.31	1	0	dialdehyde	agrochemical; allergen; pesticide; plant growth regulator
3-hydroxybutanal [no description available]	2.13	1	0
acetic anhydride acetic anhydride: RN given refers to unlabeled cpd; structure. acetic anhydride : An acyclic carboxylic anhydride derived from acetic acid.	1.98	1	0	acyclic carboxylic anhydride	metabolite; reagent
thiophenes Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.	2.69	3	0	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
diethylene glycol glycol ether : A hydroxyether which contains both an ether and alcohol functional groups. It is one of the most versatile classes of organic solvents which are commonly used in paints, cleaners, adhesives, pharmaceuticals and cosmetics.	1.97	1	0	hydroxyether
dipropyl sulfide [no description available]	2	1	0	aliphatic sulfide
4-nitrosodimethylaniline 4-nitrosodimethylaniline: structure; RN given refers to parent cpd. N,N-dimethyl-4-nitrosoaniline : A member of the class of dimethylanilines that is N,N-dimethylaniline having a nitroso group at the 4-position.	1.99	1	0	dimethylaniline; nitroso compound; tertiary amino compound
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.	5.33	21	0	catechin	antioxidant; plant metabolite
dibenzo(a,l)pyrene dibenzo(a,l)pyrene: structure in first source	2.02	1	0	ortho- and peri-fused polycyclic arene	human metabolite; 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.	2.03	1	0	acridines; mancude organic heterotricyclic parent; polycyclic heteroarene	genotoxin
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	0	diazine; pyrazines	Daphnia magna metabolite
hydrazine diamine : Any polyamine that contains two amino groups.	2.44	2	0	azane; hydrazines	EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
paraoxon [no description available]	2.01	1	0	aryl dialkyl phosphate; organophosphate insecticide	EC 3.1.1.7 (acetylcholinesterase) inhibitor; mouse metabolite
lithocholic acid Lithocholic Acid: A bile acid formed from chenodeoxycholate by bacterial action, usually conjugated with glycine or taurine. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as cholagogue and choleretic.. lithocholic acid : A monohydroxy-5beta-cholanic acid with a alpha-hydroxy substituent at position 3. It is a bile acid obtained from chenodeoxycholic acid by bacterial action.. lithocholate : A bile acid anion that is the conjugate base of lithocholic acid.	1.99	1	0	bile acid; C24-steroid; monohydroxy-5beta-cholanic acid	geroprotector; human metabolite; mouse metabolite
phosphoadenosine phosphosulfate Phosphoadenosine Phosphosulfate: 3'-Phosphoadenosine-5'-phosphosulfate. Key intermediate in the formation by living cells of sulfate esters of phenols, alcohols, steroids, sulfated polysaccharides, and simple esters, such as choline sulfate. It is formed from sulfate ion and ATP in a two-step process. This compound also is an important step in the process of sulfur fixation in plants and microorganisms.. 3'-phospho-5'-adenylyl sulfate : An adenosine bisphosphate having monophosphate groups at the 3'- and 5'-positions and a sulfo group attached to the phosphate at position 5'.	2.38	2	0	acyl sulfate; adenosine bisphosphate; purine ribonucleoside bisphosphate	Escherichia coli metabolite; mouse metabolite
flavanone flavanone: RN given refers to cpd with unspecified isomeric designation; structure in first source. flavanone : The simplest member of the class of flavanones that consists of flavan bearing an oxo substituent at position 4.	2.01	1	0	flavanones
azomethane azomethane: structure	2.02	1	0
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.	3.46	7	0
dihydrotestosterone Dihydrotestosterone: A potent androgenic metabolite of TESTOSTERONE. It is produced by the action of the enzyme 3-OXO-5-ALPHA-STEROID 4-DEHYDROGENASE.. 17beta-hydroxyandrostan-3-one : A 17beta-hydroxy steroid that is testosterone in which the 4-5 double bond has been reduced to a single bond with unspecified configuration at position 5.. 17beta-hydroxy-5alpha-androstan-3-one : A 17beta-hydroxy steroid that is testosterone in which the 4,5 double bond has been reduced to a single bond with alpha-configuration at position 5.	2.05	1	0	17beta-hydroxy steroid; 17beta-hydroxyandrostan-3-one; 3-oxo-5alpha-steroid	androgen; Daphnia magna metabolite; human metabolite; mouse metabolite
azomycin azomycin: RN given refers to parent cpd with specified locant; structure	2.41	2	0	C-nitro compound; imidazoles	antitubercular agent
malondialdehyde Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.	2.49	2	0	dialdehyde	biomarker
1-naphthylisothiocyanate 1-Naphthylisothiocyanate: A tool for the study of liver damage which causes bile stasis and hyperbilirubinemia acutely and bile duct hyperplasia and biliary cirrhosis chronically, with changes in hepatocyte function. It may cause skin and kidney damage.	2.02	1	0	isothiocyanate	insecticide
allyl sulfide allyl sulfide: essence of garlic; inhibits CYP2E1	2.71	3	0	organic sulfide
alpha-naphthoflavone alpha-naphthoflavone: inhibits P4501A1 and P4501A2; stimulates some activities of P4503A4. alpha-naphthoflavone : An extended flavonoid resulting from the formal fusion of a benzene ring with the h side of flavone. A synthetic compound, it is an inhibitor of aromatase (EC 1.14.14.14).	3.08	5	0	extended flavonoid; naphtho-gamma-pyrone; organic heterotricyclic compound	aryl hydrocarbon receptor agonist; aryl hydrocarbon receptor antagonist; EC 1.14.14.14 (aromatase) inhibitor
2-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.	1.99	1	0	nitroarene	carcinogenic agent; mutagen
2,4-dichloro-1-nitrobenzene [no description available]	2	1	0
2-anthramine 2-anthramine: structure	2.71	3	0	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	0	acetylcysteine; L-cysteine derivative; N-acetyl-L-amino acid	antidote to paracetamol poisoning; antiinfective agent; antioxidant; antiviral drug; ferroptosis inhibitor; geroprotector; human metabolite; mucolytic; radical scavenger; vulnerary
2,6-dichloro-4-nitrophenol [no description available]	1.98	1	0
2,5-dimethylfuran 2,5-dimethylfuran: metabolite of n-hexane. 2,5-dimethylfuran : A member of the class of furans that is furan in which the hydrogens at positions 2 and 5 are replaced by methyl groups.	2.11	1	0	furans	antifungal agent; bacterial metabolite; fuel; fumigant; human urinary metabolite; Maillard reaction product; plant metabolite
n-propyl disulfide n-propyl disulfide: major flavor component of onions; non-nitrogenous, pungent volatile oil. dipropyl disulfide : An organic disulfide where the alkyl groups specified are propyl. It is a component of the essential oils obtained from Allium.	2.01	1	0	organic disulfide	plant metabolite
methylnitrosourea Methylnitrosourea: A nitrosourea compound with alkylating, carcinogenic, and mutagenic properties.. N-methyl-N-nitrosourea : A member of the class of N-nitrosoureas that is urea in which one of the nitrogens is substituted by methyl and nitroso groups.	3.79	3	0	N-nitrosoureas	alkylating agent; carcinogenic agent; mutagen; teratogenic agent
ethylnitrosourea Ethylnitrosourea: A nitrosourea compound with alkylating, carcinogenic, and mutagenic properties.. N-ethyl-N-nitrosourea : A member of the class of N-nitrosoureas that is urea in which one of the nitrogens is substituted by ethyl and nitroso groups.	2.41	2	0	N-nitrosoureas	alkylating agent; carcinogenic agent; genotoxin; mutagen
n-nitrosopyrrolidine N-Nitrosopyrrolidine: Carcinogenic nitrosamine that may be formed from preservatives in meats during their preparation or in the liver during metabolism.	2.43	2	0	pyrrolidines
methylparaoxon [no description available]	2.01	1	0	C-nitro compound
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.	2.44	2	0	alpha-tocopherol	algal metabolite; antiatherogenic agent; anticoagulant; antioxidant; antiviral agent; EC 2.7.11.13 (protein kinase C) inhibitor; immunomodulator; micronutrient; nutraceutical; plant metabolite
tocopherols [no description available]	2.54	2	0
diallyl disulfide diallyl disulfide: major constituent of garlic oil. diallyl disulfide : An organic disulfide where the organic group specified is allyl. It has been isolated from garlic and other species of the genus Allium.	2.91	4	0	organic disulfide	antifungal agent; antineoplastic agent; plant metabolite
phenethyl isothiocyanate phenethyl isothiocyanate: a dietary liver aldehyde dehydrogenase inhibitor; promotes urinary bladder carcinoma. phenethyl isothiocyanate : An isothiocyanate having a phenethyl group attached to the nitrogen. It is a naturally occurring compound found in some cruciferous vegetables (e.g. watercress) and is known to possess anticancer properties.	2.71	3	0	isothiocyanate	antineoplastic agent; EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor; metabolite
3-methoxy-4-aminoazobenzene [no description available]	1.99	1	0
butylhydroxybutylnitrosamine Butylhydroxybutylnitrosamine: A substituted carcinogenic nitrosamine.. N-butyl-N-(4-hydroxybutyl)nitrosamine : A nitrosamine that has butyl and 4-hydroxybutyl substituents. In mice, it causes high-grade, invasive cancers in the urinary bladder, but not in any other tissues.	1.98	1	0	nitrosamine; primary alcohol	carcinogenic agent
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.	1.99	1	0	diastereoisomeric mixture; homocysteines; non-proteinogenic alpha-amino acid; sulfoximide	EC 6.3.2.2 (glutamate--cysteine ligase) inhibitor; ferroptosis inducer
1-nitropyrene [no description available]	2.4	2	0	nitroarene	carcinogenic agent
acetoxyacetylaminofluorene Acetoxyacetylaminofluorene: An alkylating agent that forms DNA ADDUCTS at the C-8 position in GUANINE, resulting in single strand breaks. It has demonstrated carcinogenic action.. N-acetoxy-2-acetamidofluorene : A 2-acetamidofluorene compound in which the parent 2-acetamidofluorene is substituted on nitrogen by an acetoxy group.	2.01	1	0	2-acetamidofluorenes	carcinogenic agent; mutagen
iridium Iridium: A metallic element with the atomic symbol Ir, atomic number 77, and atomic weight 192.22.	2.13	1	0	cobalt group element atom; platinum group metal atom
6-nitrochrysene 6-nitrochrysene: RN given refers to cpd with locant for nitro group in position 6	2.43	2	0	carbopolycyclic compound
sodium sulfite [no description available]	1.99	1	0	inorganic sodium salt; sulfite salt	food preservative; reducing agent
cadmium chloride Cadmium Chloride: A cadmium halide in the form of colorless crystals, soluble in water, methanol, and ethanol. It is used in photography, in dyeing, and calico printing, and as a solution to precipitate sulfides. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). cadmium dichloride : A cadmium coordination entity in which cadmium(2+) and Cl(-) ions are present in the ratio 2:1. Although considered to be ionic, it has considerable covalent character to its bonding.	2.07	1	0	cadmium coordination entity
benzo(a)pyrene 7,8-dihydrodiol benzo(a)pyrene 7,8-dihydrodiol: RN given refers to cpd without isomeric designation	1.98	1	0	pyrenes
2',3-dimethyl-4-aminobiphenyl 2',3-dimethyl-4-aminobiphenyl: RN given refers to parent cpd; structure	4.6	8	0
phosphotyrosine Phosphotyrosine: An amino acid that occurs in endogenous proteins. Tyrosine phosphorylation and dephosphorylation plays a role in cellular signal transduction and possibly in cell growth control and carcinogenesis.. O(4)-phospho-L-tyrosine : A non-proteinogenic L-alpha-amino acid that is L-tyrosine phosphorylated at the phenolic hydroxy group.	2.03	1	0	L-tyrosine derivative; non-proteinogenic L-alpha-amino acid; O(4)-phosphotyrosine	Escherichia coli metabolite; immunogen
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.	2.01	1	0	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
transferrin Transferrin: An iron-binding beta1-globulin that is synthesized in the LIVER and secreted into the blood. It plays a central role in the transport of IRON throughout the circulation. A variety of transferrin isoforms exist in humans, including some that are considered markers for specific disease states.	1.99	1	0
azoxymethane Azoxymethane: A potent carcinogen and neurotoxic compound. It is particularly effective in inducing colon carcinomas.	3.12	5	0
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	1.99	1	0	aromatic ketone
1,2,7,8-tetrachlorodibenzo-p-dioxin 1,2,7,8-tetrachlorodibenzo-p-dioxin: structure in first source	2.04	1	0
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).	3.36	7	0
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.	1.98	1	0	diol; nitrosamine; secondary alcohol	carcinogenic agent
nitrosobis(2-oxopropyl)amine nitrosobis(2-oxopropyl)amine: structure. nitrosobis(2-oxopropyl)amine : A nitrosamine that is iminodiacetone that is substituted by a nitroso group at the N-atom. It induces pancreatic ductal adenocarcinomas in Syrian golden hamsters (other rodents are not susceptible).	3.1	1	0	ketone; nitrosamine	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	3.14	5	0	nitrosamine; pyridines
oltipraz oltipraz : A 1,2-dithiole that is 3H-1,2-dithiole-3-thione substituted at positions 4 and 5 by methyl and pyrazin-2-yl groups respectively.	2.39	2	0	1,2-dithiole; pyrazines	angiogenesis modulating agent; antimutagen; antineoplastic agent; antioxidant; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; neurotoxin; protective agent; schistosomicide drug
glu-p-2 Glu-P-2: RN given refers to parent cpd	2.9	4	0	imidazopyridine
2-amino-6-methyldipyrido(1,2-a-3',2'-d)imidazole 2-amino-6-methyldipyrido(1,2-a-3',2'-d)imidazole: structure	3.85	12	0	imidazopyridine
2-amino-3-methylimidazo(4,5-f)quinoline 2-amino-3-methylimidazo(4,5-f)quinoline: mutagen found in broiled food; RN given refers to parent cpd; structure given in first source; frequently abbreviated as IQ in the literature. 3-methyl-3H-imidazo[4,5-f]quinolin-2-amine : An imidazoquinoline that is 3H-imidazo[4,5-f]quinoline substituted by a methyl group at position 3 and an amino group at position 2.	8.32	92	0	imidazoquinoline	carcinogenic agent
adenosine quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit	2.11	1	0	adenosines; purines D-ribonucleoside	analgesic; anti-arrhythmia drug; fundamental metabolite; human metabolite; vasodilator agent
dimethylhydrazines Dimethylhydrazines: Hydrazines substituted with two methyl groups in any position.	2.38	2	0
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	2.9	4	0	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	8.71	45	0	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.	12.82	146	3	aromatic amine; imidazoquinoxaline	carcinogenic agent; genotoxin; Maillard reaction product; mutagen
isothiocyanic acid [no description available]	2.02	1	0	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	3.81	11	0	pyridoindole
glucose, (beta-d)-isomer beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.	2.7	3	0	D-glucopyranose	epitope; mouse metabolite
norharman norharman: RN given refers to parent cpd. beta-carboline : The parent compound of the beta-carbolines, a tricyclic structure comprising an indole ring system ortho- fused to C-3 and C-4 of a pyridine ring.	3.56	8	0	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.	3.63	9	0	flavans; gallate ester; polyphenol	antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite
gallocatechol gallocatechol: structure give in first source; RN given for (trans-(+-))-omer; inhibits DNA-dependent DNA & RNA polymerases. (+)-gallocatechin : A gallocatechin that has (2R,3S)-configuration. It is found in green tea and bananas.. gallocatechin : A catechin that is a flavan substituted by hydroxy groups at positions 3, 3', 4', 5, 5' and 7 (the trans isomer). It is isolated from Acacia mearnsii.	2	1	0	gallocatechin	antioxidant; metabolite; radical scavenger
bathocuproine bathocuproine: reagent for copper; RN given refers to parent cpd	2.01	1	0
1,7-phenanthroline [no description available]	2.01	1	0	phenanthroline
alpha-carboline alpha-carboline: RN given refers to unlabeled cpd; structure given in first source	1.99	1	0	pyridoindole
1h-tetrazole tetrazole : An azaarene that is a five-membered ring composed of 4 nitrogen and 1 carbon atom.. 2H-tetrazole : A tetrazole tautomer where the proton is located on the 2 position.	2.03	1	0	one-carbon compound; tetrazole
tangeretin tangeretin: structure given in first source; from citrus plants; inhibits invasion of MO4 mouse cells into embryonic chick heart in vitro. tangeretin : A pentamethoxyflavone flavone with methoxy groups at positions 4', 5, 6 , 7 and 8.. pentamethoxyflavone : A methoxyflavone that is flavone substituted by a five methoxy groups.	2.4	2	0	pentamethoxyflavone	antineoplastic agent; plant metabolite
delphinidin Paraffin: A mixture of solid hydrocarbons obtained from petroleum. It has a wide range of uses including as a stiffening agent in ointments, as a lubricant, and as a topical anti-inflammatory. It is also commonly used as an embedding material in histology.. delphinidin chloride : An anthocyanidin chloride that has delphinidin as the cationic counterpart.	2	1	0	anthocyanidin chloride
1,2-dithiol-3-thione 1,2-dithiol-3-thione: has antioxidant activity; structure given in first source	2	1	0	1,2-dithiole
nobiletin nobiletin : A methoxyflavone that is flavone substituted by methoxy groups at positions 5, 6, 7, 8, 3' and 4' respectively.	2.06	1	0	methoxyflavone	antineoplastic agent; plant metabolite
2-amino-1-methylbenzimidazole 2-amino-1-methylbenzimidazole: structure in first source	2.11	1	0	benzimidazoles
reuterin [no description available]	2.13	1	0	alpha-CH2-containing aldehyde; propanals
n-hydroxy-4-aminobiphenyl [no description available]	2.03	1	0	aminobiphenyl; N-substituted amine	carcinogenic agent; human xenobiotic metabolite
2-aminoimidazole 2-aminoimidazole: from catabolism of arginine	2.1	1	0
nicotine (S)-nicotine : A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has S-configuration. The naturally occurring and most active enantiomer of nicotine, isolated from Nicotiana tabacum.	2.44	2	0	3-(1-methylpyrrolidin-2-yl)pyridine	anxiolytic drug; biomarker; immunomodulator; mitogen; neurotoxin; nicotinic acetylcholine receptor agonist; peripheral nervous system drug; phytogenic insecticide; plant metabolite; psychotropic drug; teratogenic agent; xenobiotic
glycidamide glycidamide: metabolite of acrylamide; structure given in first source	2.76	3	0
delta-tocopherol [no description available]	2.15	1	0	tocopherol; vitamin E	food antioxidant; plant metabolite
gamma-tocopherol gamma-Tocopherol: A natural tocopherol with less antioxidant activity than ALPHA-TOCOPHEROL. It exhibits antioxidant activity by virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus. As in BETA-TOCOPHEROL, it also has three methyl groups on the 6-chromanol nucleus but at different sites.. gamma-tocopherol : A tocopherol in which the chroman-6-ol core is substituted by methyl groups at positions 7 and 8. It is found particularly in maize (corn) oil and soya bean (soybean) oils.	2.15	1	0	tocopherol; vitamin E	algal metabolite; food antioxidant; plant metabolite
pyrimidine dimers Pyrimidine Dimers: Dimers found in DNA chains damaged by ULTRAVIOLET RAYS. They consist of two adjacent PYRIMIDINE NUCLEOTIDES, usually THYMINE nucleotides, in which the pyrimidine residues are covalently joined by a cyclobutane ring. These dimers block DNA REPLICATION.	1.99	1	0
glucuronic acid Glucuronic Acid: A sugar acid formed by the oxidation of the C-6 carbon of GLUCOSE. In addition to being a key intermediate metabolite of the uronic acid pathway, glucuronic acid also plays a role in the detoxification of certain drugs and toxins by conjugating with them to form GLUCURONIDES.. D-glucuronic acid : The D-enantiomer of glucuronic acid.. D-glucopyranuronic acid : A D-glucuronic acid in cyclic pyranose form.	1.97	1	0	D-glucuronic acid	algal metabolite
arctiin arctiin: from fruits of Arctium lappa L; RN given refers to (3R-trans)-isomer; RN for cpd without isomeric designation not avail 12/92	2	1	0	glycoside; lignan
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	6.82	34	2	quinoxaline derivative
fulvestrant Fulvestrant: An estradiol derivative and estrogen receptor antagonist that is used for the treatment of estrogen receptor-positive, locally advanced or metastatic breast cancer.. fulvestrant : A 3-hydroxy steroid that is 17beta-estradiol in which the 7alpha hydrogen has been replaced by a nonyl group in which one of the hydrogens of the terminal methyl has been replaced by a (4,4,5,5,5-pentafluoropentyl)sulfinyl group. An estrogen receptor antagonist, it is used in the treatment of breast cancer.	2.72	3	0	17beta-hydroxy steroid; 3-hydroxy steroid; organofluorine compound; sulfoxide	antineoplastic agent; estrogen antagonist; estrogen receptor antagonist
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	4.69	9	0
2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine: directly acting genotoxic metabolite of 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine. N-hydroxy-PhIP : An imidazopyridine that is 1H--imidazo[4,5-b]pyridine which is substituted at positions 1, 2, and 6 by methyl, hydoxyamino, and phenyl groups, respectively. The active metabolite of the dietary carcinogen PhIP.	4.4	21	0	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	2.4	2	0	quinolines
pentoxyresorufin [no description available]	1.99	1	0
procyanidin Proanthocyanidins: Dimers and oligomers of flavan-3-ol units (CATECHIN analogs) linked mainly through C4 to C8 bonds to leucoanthocyanidins. They are structurally similar to ANTHOCYANINS but are the result of a different fork in biosynthetic pathways.	2.42	2	0	proanthocyanidin
epicatechin gallate epicatechin gallate: a steroid 5alpha-reductase inhibitor; RN given refers to the (cis)-isomer; structure given in first source; isolated from green tea. (-)-epicatechin-3-O-gallate : A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of epicatechin. A natural product found in Parapiptadenia rigida.	3.64	3	0	catechin; gallate ester; polyphenol	EC 3.2.1.1 (alpha-amylase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; metabolite
cafestol [no description available]	3.8	3	0	diterpenoid; furans; organic heteropentacyclic compound; primary alcohol; tertiary alcohol	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; antioxidant; apoptosis inducer; hypoglycemic agent; plant metabolite
proanthocyanidin proanthocyanidin: RN given refers to proanthocyanidin A; Cannabinoid Receptor CB1 antagonist. proanthocyanidin : A flavonoid oligomer obtained by the the condensation of two or more units of hydroxyflavans.	2.01	1	0
1-hexadecyl-2-acetyl-glycero-3-phosphocholine Platelet Activating Factor: A phospholipid derivative formed by PLATELETS; BASOPHILS; NEUTROPHILS; MONOCYTES; and MACROPHAGES. It is a potent platelet aggregating agent and inducer of systemic anaphylactic symptoms, including HYPOTENSION; THROMBOCYTOPENIA; NEUTROPENIA; and BRONCHOCONSTRICTION.. 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine : A 2-acetyl-1-alkyl-sn-glycero-3-phosphocholine betaine which has hexadecyl as the alkyl group. PAF is a potent phospholipid activator and mediator of many leukocyte functions, including platelet aggregation, inflammation, and anaphylaxis.	2.01	1	0	2-acetyl-1-alkyl-sn-glycero-3-phosphocholine	antihypertensive agent; beta-adrenergic antagonist; bronchoconstrictor agent; hematologic agent; vasodilator agent
2-amino-1-methyl-6-(4-hydroxyphenyl)imidazo(4,5-b)pyridine 2-amino-1-methyl-6-(4-hydroxyphenyl)imidazo(4,5-b)pyridine: structure given in first source	2.96	4	0
kahweol [no description available]	4.02	4	0	diterpenoid; furans; organic heteropentacyclic compound; primary alcohol; tertiary alcohol	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; antioxidant; apoptosis inducer; plant metabolite
1-o-hexyl-2,3,5-trimethylhydroquinone [no description available]	2.4	2	0
elacridar Elacridar: inhibitor of MDR1 PROTEIN; structure given in first source	2.03	1	0
proline Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.	2.31	1	0	amino acid zwitterion; glutamine family amino acid; L-alpha-amino acid; proline; proteinogenic amino acid	algal metabolite; compatible osmolytes; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
tracheloside tracheloside: a lignan isolated from the seeds of Arctium lappa and Carthamus tinctorius; structure given in first source	2.01	1	0	glycoside; lignan	metabolite
lignin Lignin: The most abundant natural aromatic organic polymer found in all vascular plants. Lignin together with cellulose and hemicellulose are the major cell wall components of the fibers of all wood and grass species. Lignin is composed of coniferyl, p-coumaryl, and sinapyl alcohols in varying ratios in different plant species. (From Merck Index, 11th ed). lignin : A polyphenylpropanoid derived from three monolignol monomers: trans-p-coumaryl alcohol, coniferol and trans-sinapyl alcohol. There is extensive cross-linking and no defined primary structure.	2.03	1	0
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.	5.62	14	0	aflatoxin; aromatic ether; aromatic ketone	carcinogenic agent; human metabolite
deoxycholic acid Deoxycholic Acid: A bile acid formed by bacterial action from cholate. It is usually conjugated with glycine or taurine. Deoxycholic acid acts as a detergent to solubilize fats for intestinal absorption, is reabsorbed itself, and is used as a choleretic and detergent.. deoxycholic acid : A bile acid that is 5beta-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 12 respectively.	2.01	1	0	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human blood serum metabolite
3-nitrotyrosine 3-nitrotyrosine: RN given refers to parent cpd without isomeric designation. 3-nitrotyrosine : A nitrotyrosine comprising tyrosine having a nitro group at the 3-position on the phenyl ring.	2.55	2	0	2-nitrophenols; C-nitro compound; nitrotyrosine; non-proteinogenic alpha-amino acid
5-hydroxymethylfurfural 5-hydroxymethylfurfural: has antisickling activity; HMF is the causative component in honey that affects the presystemic metabolism and pharmacokinetics of GZ in-vivo. 5-hydroxymethylfurfural : A member of the class of furans that is furan which is substituted at positions 2 and 5 by formyl and hydroxymethyl substituents, respectively. Virtually absent from fresh foods, it is naturally generated in sugar-containing foods during storage, and especially by drying or cooking. It is the causative component in honey that affects the presystemic metabolism and pharmacokinetics of GZ in-vivo.	2.49	2	0	arenecarbaldehyde; furans; primary alcohol	indicator; Maillard reaction product
aminoflavone aminoflavone: structure in first source	3.15	1	0
carnosine polaprezinc: stimulates bone growth	2.31	1	0	amino acid zwitterion; dipeptide	anticonvulsant; antineoplastic agent; antioxidant; Daphnia magna metabolite; geroprotector; human metabolite; mouse metabolite; neuroprotective agent
naringenin (S)-naringenin : The (S)-enantiomer of naringenin.	3.63	3	0	(2S)-flavan-4-one; naringenin	expectorant; plant metabolite
quinidine Quinidine: An optical isomer of quinine, extracted from the bark of the CHINCHONA tree and similar plant species. This alkaloid dampens the excitability of cardiac and skeletal muscles by blocking sodium and potassium currents across cellular membranes. It prolongs cellular ACTION POTENTIALS, and decreases automaticity. Quinidine also blocks muscarinic and alpha-adrenergic neurotransmission.. quinidine : A cinchona alkaloid consisting of cinchonine with the hydrogen at the 6-position of the quinoline ring substituted by methoxy.	1.97	1	0	cinchona alkaloid	alpha-adrenergic antagonist; anti-arrhythmia drug; antimalarial; drug allergen; EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor; EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor; muscarinic antagonist; P450 inhibitor; potassium channel blocker; sodium channel blocker
naringin [no description available]	2	1	0	(2S)-flavan-4-one; 4'-hydroxyflavanones; dihydroxyflavanone; disaccharide derivative; neohesperidoside	anti-inflammatory agent; antineoplastic agent; metabolite
lignans Lignans: A class of dibenzylbutane derivatives which occurs in higher plants and in fluids (bile, serum, urine, etc.) in man and other animals. These compounds, which have a potential anti-cancer role, can be synthesized in vitro by human fecal flora. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)	2.01	1	0
acetyl coenzyme a Acetyl Coenzyme A: Acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent.	2.4	2	0	acyl-CoA	acyl donor; coenzyme; effector; fundamental metabolite
ergosterol [no description available]	2.11	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; ergostanoid; phytosterols	fungal metabolite; Saccharomyces cerevisiae metabolite
tretinoin Tretinoin: An important regulator of GENE EXPRESSION during growth and development, and in NEOPLASMS. Tretinoin, also known as retinoic acid and derived from maternal VITAMIN A, is essential for normal GROWTH; and EMBRYONIC DEVELOPMENT. An excess of tretinoin can be teratogenic. It is used in the treatment of PSORIASIS; ACNE VULGARIS; and several other SKIN DISEASES. It has also been approved for use in promyelocytic leukemia (LEUKEMIA, PROMYELOCYTIC, ACUTE).. retinoic acid : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraenoic acid substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).. all-trans-retinoic acid : A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry.	2.02	1	0	retinoic acid; vitamin A	anti-inflammatory agent; antineoplastic agent; antioxidant; AP-1 antagonist; human metabolite; keratolytic drug; retinoic acid receptor agonist; retinoid X receptor agonist; signalling molecule
arachidonic acid icosa-5,8,11,14-tetraenoic acid : Any icosatetraenoic acid with the double bonds at positions 5, 8, 11 and 14.. arachidonate : A long-chain fatty acid anion resulting from the removal of a proton from the carboxy group of arachidonic acid.	1.98	1	0	icosa-5,8,11,14-tetraenoic acid; long-chain fatty acid; omega-6 fatty acid	Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite; mouse metabolite
resveratrol trans-resveratrol : A resveratrol in which the double bond has E configuration.	3	4	0	resveratrol	antioxidant; phytoalexin; plant metabolite; quorum sensing inhibitor; radical scavenger
retinol Vitamin A: Retinol and derivatives of retinol that play an essential role in metabolic functioning of the retina, the growth of and differentiation of epithelial tissue, the growth of bone, reproduction, and the immune response. Dietary vitamin A is derived from a variety of CAROTENOIDS found in plants. It is enriched in the liver, egg yolks, and the fat component of dairy products.. vitamin A : Any member of a group of fat-soluble retinoids produced via metabolism of provitamin A carotenoids that exhibit biological activity against vitamin A deficiency. Vitamin A is involved in immune function, vision, reproduction, and cellular communication.. all-trans-retinol : A retinol in which all four exocyclic double bonds have E- (trans-) geometry.. retinol : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraen-1-ol substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).	1.99	1	0	retinol; vitamin A	human metabolite; mouse metabolite; plant metabolite
lycopene [no description available]	2.92	4	0	acyclic carotene	antioxidant; plant metabolite
imidazolidines [no description available]	2.41	1	0	azacycloalkane; imidazolidines; saturated organic heteromonocyclic parent
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	0	3-phenylprop-2-enal; cinnamaldehydes	antifungal agent; EC 4.3.1.24 (phenylalanine ammonia-lyase) inhibitor; flavouring agent; hypoglycemic agent; plant metabolite; sensitiser; vasodilator agent
glycosides [no description available]	2.31	1	0
isosafrole isosafrole: RN given refers to cpd without isomeric designation	1.97	1	0	benzodioxoles
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	2.76	3	0	stilbene
xanthohumol xanthohumol: from hop plant, Humulus lupulus. xanthohumol : A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 4, 2' and 4', a methoxy group at position 6' and a prenyl group at position 3'. Isolated from Humulus lupulus, it induces apoptosis in human malignant glioblastoma cells.	2.07	1	0	aromatic ether; chalcones; polyphenol	anti-HIV-1 agent; antineoplastic agent; antiviral agent; apoptosis inducer; EC 2.3.1.20 (diacylglycerol O-acyltransferase) inhibitor; metabolite
sesquiterpenes [no description available]	2.02	1	0
caffeic acid trans-caffeic acid : The trans-isomer of caffeic acid.	2.57	2	0	caffeic acid	geroprotector; mouse metabolite
curcumin Curcumin: A yellow-orange dye obtained from tumeric, the powdered root of CURCUMA longa. It is used in the preparation of curcuma paper and the detection of boron. Curcumin appears to possess a spectrum of pharmacological properties, due primarily to its inhibitory effects on metabolic enzymes.. curcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa.	2.72	3	0	aromatic ether; beta-diketone; diarylheptanoid; enone; polyphenol	anti-inflammatory agent; antifungal agent; antineoplastic agent; biological pigment; contraceptive drug; dye; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; EC 1.8.1.9 (thioredoxin reductase) inhibitor; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; flavouring agent; food colouring; geroprotector; hepatoprotective agent; immunomodulator; iron chelator; ligand; lipoxygenase inhibitor; metabolite; neuroprotective agent; nutraceutical; radical scavenger
sulindac Sulindac: A sulfinylindene derivative prodrug whose sulfinyl moiety is converted in vivo to an active NSAID analgesic. Specifically, the prodrug is converted by liver enzymes to a sulfide which is excreted in the bile and then reabsorbed from the intestine. This helps to maintain constant blood levels with reduced gastrointestinal side effects.. sulindac : A monocarboxylic acid that is 1-benzylidene-1H-indene which is substituted at positions 2, 3, and 5 by methyl, carboxymethyl, and fluorine respectively, and in which the phenyl group of the benzylidene moiety is substituted at the para position by a methylsulfinyl group. It is a prodrug for the corresponding sulfide, a non-steroidal anti-inflammatory drug, used particularly in the treatment of acute and chronic inflammatory conditions.	2.01	1	0	monocarboxylic acid; organofluorine compound; sulfoxide	analgesic; antineoplastic agent; antipyretic; apoptosis inducer; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; prodrug; tocolytic agent
tamoxifen [no description available]	1.97	1	0	stilbenoid; tertiary amino compound	angiogenesis inhibitor; antineoplastic agent; bone density conservation agent; EC 1.2.3.1 (aldehyde oxidase) inhibitor; EC 2.7.11.13 (protein kinase C) inhibitor; estrogen antagonist; estrogen receptor antagonist; estrogen receptor modulator
1,1-diphenyl-2-picrylhydrazyl 1,1-diphenyl-2-picrylhydrazyl: A diphenyl picrate; the ability to decolorize this stable radical indicates reactivity of tested compounds (Banda, Anal Chem 46:1772-7 1974)	2.13	1	0
2-nitro-3-methylimidazo(4,5-f)quinoline 2-nitro-3-methylimidazo(4,5-f)quinoline: structure given in first source	2.4	2	0
mtt formazan MTT formazan: a blue MEM-insoluble mitochondrial byproduct; used to determine viability of cells with active mitochondrial dehydrogenase enzymes	1.98	1	0
alpha-chymotrypsin Chymotrypsin: A serine endopeptidase secreted by the pancreas as its zymogen, CHYMOTRYPSINOGEN and carried in the pancreatic juice to the duodenum where it is activated by TRYPSIN. It selectively cleaves aromatic amino acids on the carboxyl side.	2.1	1	0
quercetin [no description available]	3.82	11	0	7-hydroxyflavonol; pentahydroxyflavone	antibacterial agent; antineoplastic agent; antioxidant; Aurora kinase inhibitor; chelator; EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor; geroprotector; phytoestrogen; plant metabolite; protein kinase inhibitor; radical scavenger
ubiquinone q2 Ubiquinone Q2: interacts with iron atom to form acceptor quinone complex; RN given refers to cpd with unspecified isomeric designation	1.99	1	0	ubiquinones
apigenin Chamomile: Common name for several daisy-like plants (MATRICARIA; TRIPLEUROSPERMUM; ANTHEMIS; CHAMAEMELUM) native to Europe and Western Asia, now naturalized in the United States and Australia.	2	1	0	trihydroxyflavone	antineoplastic agent; metabolite
linoleic acid Linoleic Acid: A doubly unsaturated fatty acid, occurring widely in plant glycosides. It is an essential fatty acid in mammalian nutrition and is used in the biosynthesis of prostaglandins and cell membranes. (From Stedman, 26th ed). linoleic acid : An octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry.	3.71	10	0	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	0
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.	2.4	2	0	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	0	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite
kaempferol [no description available]	2.01	1	0	7-hydroxyflavonol; flavonols; tetrahydroxyflavone	antibacterial agent; geroprotector; human blood serum metabolite; human urinary metabolite; human xenobiotic metabolite; plant metabolite
alpha-linolenic acid linolenic acid : A two-membered subclass of octadecatrienoic acid comprising the (9Z,12Z,15Z)- and (6Z,9Z,12Z)-isomers. Linolenic acids are nutrients essential to the formation of prostaglandins and are also used in making paints and synthetic resins.. linolenate : A polyunsaturated fatty acid anion obtained by deprotonation of the carboxy group of either alpha- or gamma-linolenic acid.	2.01	1	0	linolenic acid; omega-3 fatty acid	micronutrient; mouse metabolite; nutraceutical
harmine Harmine: Alkaloid isolated from seeds of PEGANUM HARMALA; ZYGOPHYLLACEAE. It is identical to banisterine, or telepathine, from Banisteria caapi and is one of the active ingredients of hallucinogenic drinks made in the western Amazon region from related plants. It has no therapeutic use, but (as banisterine) was hailed as a cure for postencephalitic PARKINSON DISEASE in the 1920's.. harmine : A harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7.	3.76	10	0	harmala alkaloid	anti-HIV agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; metabolite
genistein [no description available]	2.69	3	0	7-hydroxyisoflavones	antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; geroprotector; human urinary metabolite; phytoestrogen; plant metabolite; tyrosine kinase inhibitor
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.	3.57	8	0	harmala alkaloid; indole alkaloid fundamental parent; indole alkaloid	anti-HIV agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; plant metabolite
chrysin chrysin : A dihydroxyflavone in which the two hydroxy groups are located at positions 5 and 7.	2.7	3	0	7-hydroxyflavonol; dihydroxyflavone	anti-inflammatory agent; antineoplastic agent; antioxidant; EC 2.7.11.18 (myosin-light-chain kinase) inhibitor; hepatoprotective agent; plant metabolite
mangiferin shamimin: isolated from the leaves of Bombax ceiba; structure in first source	2.31	1	0	C-glycosyl compound; xanthones	anti-inflammatory agent; antioxidant; hypoglycemic agent; plant metabolite
myricetin [no description available]	2.81	3	0	7-hydroxyflavonol; hexahydroxyflavone	antineoplastic agent; antioxidant; cyclooxygenase 1 inhibitor; food component; geroprotector; hypoglycemic agent; plant metabolite
daidzein [no description available]	1.99	1	0	7-hydroxyisoflavones	antineoplastic agent; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; phytoestrogen; plant metabolite
shogaol shogaol: from ginger, ZINGIBER OFFICINALE; less mutagenic than GINGEROL; structure given in first source	2.21	1	0	enone; monomethoxybenzene; phenols
3-amino-1,4-dimethyl-5h-pyrido(4,3-b)indole 3-amino-1,4-dimethyl-5H-pyrido(4,3-b)indole: structure	3.69	10	0	pyridoindole
3-amino-1-methyl-5h-pyrido(4,3-b)indole 3-amino-1-methyl-5H-pyrido(4,3-b)indole: structure	5.17	11	0	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	0	cytochalasin; lactam; lactone; organic heterotricyclic compound	actin polymerisation inhibitor; metabolite; mycotoxin; platelet aggregation inhibitor
ag-490 [no description available]	2	1	0	catechols; enamide; monocarboxylic acid amide; nitrile; secondary carboxamide	anti-inflammatory agent; antioxidant; apoptosis inducer; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; geroprotector; STAT3 inhibitor
ethylmorphine Ethylmorphine: A narcotic analgesic and antitussive. It is metabolized in the liver by ETHYLMORPHINE-N-DEMETHYLASE and used as an indicator of liver function.	1.98	1	0	morphinane alkaloid
sulfur Sulfur: An element that is a member of the chalcogen family. It has an atomic symbol S, atomic number 16, and atomic weight [32.059; 32.076]. It is found in the amino acids cysteine and methionine.	2.01	1	0	chalcogen; nonmetal atom	macronutrient
deoxyribose [no description available]	1.98	1	0	deoxypentose	human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	2.72	3	0	cysteinium	fundamental metabolite
caftaric acid [no description available]	2.06	1	0	hydroxycinnamic acid
4-oxo-2-nonenal 4-oxo-2-nonenal: reacts with 2'-deoxyguanosine; a product of lipid peroxidation; structure in first source. (E)-4-oxonon-2-enal : The enal that is (E)-non-2-enal substituted with an oxo group at C-4.	2.49	2	0	enal; enone	human metabolite
verlukast verlukast: LTD4 receptor antagonist	2.03	1	0
sq-23377 Ionomycin: A divalent calcium ionophore that is widely used as a tool to investigate the role of intracellular calcium in cellular processes.. ionomycin : A very long-chain fatty acid that is docosa-10,16-dienoic acid which is substituted by methyl groups at positions 4, 6, 8, 12, 14, 18 and 20, by hydroxy groups at positions 11, 19 and 21, and by a (2',5-dimethyloctahydro-2,2'-bifuran-5-yl)ethanol group at position 21. An ionophore produced by Streptomyces conglobatus, it is used in research to raise the intracellular level of Ca(2+) and as a research tool to understand Ca(2+) transport across biological membranes.	2.04	1	0	cyclic ether; enol; polyunsaturated fatty acid; very long-chain fatty acid	calcium ionophore; 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	0
s-allylcysteine S-allylcysteine: structure in first source; RN given refers to (L)-isomer. S-allylcysteine : An S-hydrocarbyl-L-cysteine that is L-cysteine in which the hydrogen attached to the sulphur is replaced by a prop-2-enyl group. It commonly occurs in garlic and has been found to exhibit antineoplastic activity.	2.41	1	0	L-alpha-amino acid zwitterion; S-hydrocarbyl-L-cysteine	antineoplastic agent; metabolite
ono 8711 ONO 8711: a prostaglandin E receptor EP1 antagonist; structure in first source	2	1	0
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	0
ribose ribopyranose : The pyranose form of ribose.	1.98	1	0	D-ribose; ribopyranose
4-(2-phenyl-5,7-bis(trifluoromethyl)pyrazolo(1,5-a)pyrimidin-3-yl)phenol 4-(2-phenyl-5,7-bis(trifluoromethyl)pyrazolo(1,5-a)pyrimidin-3-yl)phenol: a selective estrogen receptor modulator	2.04	1	0	pyrazoles; ring assembly
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	1	0
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	2.01	1	0	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
tannins Tannins: Polyphenolic compounds with molecular weights of around 500-3000 daltons and containing enough hydroxyl groups (1-2 per 100 MW) for effective cross linking of other compounds (ASTRINGENTS). The two main types are HYDROLYZABLE TANNINS and CONDENSED TANNINS. Historically, the term has applied to many compounds and plant extracts able to render skin COLLAGEN impervious to degradation. The word tannin derives from the Celtic word for OAK TREE which was used for leather processing.	2	1	0
oligonucleotides [no description available]	3.14	5	0
cellulose DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.	1.99	1	0	glycoside
ubiquinone Ubiquinone: A lipid-soluble benzoquinone which is involved in ELECTRON TRANSPORT in mitochondrial preparations. The compound occurs in the majority of aerobic organisms, from bacteria to higher plants and animals.	1.99	1	0
chitosan [no description available]	2.31	1	0
sodium bisulfite sodium bisulfite: has been used externally for parasitic skin diseases and as gastrointestinal antiseptic; structure. sodium hydrogensulfite : An inorganic sodium salt having hydrogensulfite as the counterion.	2.01	1	0	inorganic sodium salt; sulfite salt	allergen; food antioxidant; food colour retention agent; mutagen; reducing agent
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	0	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.	2.1	1	0
2-(acetoxyamino)-1-methyl-6-phenylimidazo(4,5-b)pyridine [no description available]	2.07	1	0	phenylpyridine
interleukin-8 Interleukin-8: A member of the CXC chemokine family that plays a role in the regulation of the acute inflammatory response. It is secreted by variety of cell types and induces CHEMOTAXIS of NEUTROPHILS and other inflammatory cells.	2.04	1	0
heme Heme: The color-furnishing portion of hemoglobin. It is found free in tissues and as the prosthetic group in many hemeproteins.. ferroheme : Any iron(II)--porphyrin coordination complex.. ferroheme b : Heme b in which the iron has oxidation state +2.. heme : A heme is any tetrapyrrolic chelate of iron.	1.97	1	0
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	3.85	2	1	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.	2.4	2	0	benzenes; hydroxycoumarin; methyl ketone
phytoestrogens Phytoestrogens: Compounds derived from plants, primarily ISOFLAVONES that mimic or modulate endogenous estrogens, usually by binding to ESTROGEN RECEPTORS.	2	1	0
okadaic acid Okadaic Acid: A specific inhibitor of phosphoserine/threonine protein phosphatase 1 and 2a. It is also a potent tumor promoter. It is produced by DINOFLAGELLATES and causes diarrhetic SHELLFISH POISONING.. okadaic acid : A polycyclic ether that is produced by several species of dinoflagellates, and is known to accumulate in both marine sponges and shellfish. A polyketide, polyether derivative of a C38 fatty acid, it is one of the primary causes of diarrhetic shellfish poisoning (DSP). It is a potent inhibitor of specific protein phosphatases and is known to have a variety of negative effects on cells.	1.98	1	0	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	2.11	1	0
cyclin d1 Cyclin D1: Protein encoded by the bcl-1 gene which plays a critical role in regulating the cell cycle. Overexpression of cyclin D1 is the result of bcl-1 rearrangement, a t(11;14) translocation, and is implicated in various neoplasms.	3.15	5	0
caseins Caseins: A mixture of related phosphoproteins occurring in milk and cheese. The group is characterized as one of the most nutritive milk proteins, containing all of the common amino acids and rich in the essential ones.	2.4	2	0
thearubigin thearubigin: from black tea leaves; a catechin oxidized product; a mixture of heterogenous polyphenols	2.39	2	0
cafestol palmitate [no description available]	2.42	2	0
nitrophenols Nitrophenols: PHENOLS carrying nitro group substituents.	1.98	1	0
glucagon-like peptide 2 Glucagon-Like Peptide 2: A 33-amino acid peptide derived from the C-terminal of PROGLUCAGON and mainly produced by the INTESTINAL L CELLS. It stimulates intestinal mucosal growth and decreased apoptosis of ENTEROCYTES. GLP-2 enhances gastrointestinal function and plays an important role in nutrient homeostasis.	2.07	1	0
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.	1.98	1	0
lactoferrin Lactoferrin: An iron-binding protein that was originally characterized as a milk protein. It is widely distributed in secretory fluids and is found in the neutrophilic granules of LEUKOCYTES. The N-terminal part of lactoferrin possesses a serine protease which functions to inactivate the TYPE III SECRETION SYSTEM used by bacteria to export virulence proteins for host cell invasion.	2.02	1	0
muramidase Muramidase: A basic enzyme that is present in saliva, tears, egg white, and many animal fluids. It functions as an antibacterial agent. The enzyme catalyzes the hydrolysis of 1,4-beta-linkages between N-acetylmuramic acid and N-acetyl-D-glucosamine residues in peptidoglycan and between N-acetyl-D-glucosamine residues in chitodextrin. EC 3.2.1.17.	2.02	1	0
deoxyguanosine [no description available]	4.21	17	0	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
guanine [no description available]	2.92	4	0	2-aminopurines; oxopurine; purine nucleobase	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
folic acid folcysteine: used to promote fertility in chickens. vitamin B9 : Any B-vitamin that exhibits biological activity against vitamin B9 deficiency. Vitamin B9 refers to the many forms of folic acid and its derivatives, including tetrahydrofolic acid (the active form), methyltetrahydrofolate (the primary form found in blood), methenyltetrahydrofolate, folinic acid amongst others. They are present in abundance in green leafy vegetables, citrus fruits, and animal products. Lack of vitamin B9 leads to anemia, a condition in which the body cannot produce sufficient number of red blood cells. Symptoms of vitamin B9 deficiency include fatigue, muscle weakness, and pale skin.	2.07	1	0	folic acids; N-acyl-amino acid	human metabolite; mouse metabolite; nutrient
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	4.62	4	0	nitroso compound	alkylating agent
8-hydroxy-2'-deoxyguanosine 8-Hydroxy-2'-Deoxyguanosine: Common oxidized form of deoxyguanosine in which C-8 position of guanine base has a carbonyl group.. 8-hydroxy-2'-deoxyguanosine : Guanosine substituted at the purine 8-position by a hydroxy group. It is used as a biomarker of oxidative DNA damage.	2.94	4	0	guanosines	biomarker
n-(deoxyguanosin-8-yl)-2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine N-(deoxyguanosin-8-yl)-2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine: structure given in first source; major adduct formed by the food-borne carcinogen 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine with DNA	3.25	6	0
alcian blue Alcian Blue: A copper-containing dye used as a gelling agent for lubricants, for staining of bacteria and for the dyeing of histiocytes and fibroblasts in vivo.	2.02	1	0
lipoteichoic acid lipoteichoic acid: lipopolysaccharides with an acyl group anchored to the cell membrane of gram-positive bacteria; functions as an adhesion molecule to facilitate the binding of bacteria to cells, colonization, and invasion; interacts with CD14 to induce NF-κB activation and inflammatory cytokine production; can function as surface antigen; inhibits remineraliztion of artificial lesions and surface-softened enamels;. lipoteichoic acid : A teichoic acid which is covalently bound to a lipid.	2.05	1	0
phosphorus radioisotopes Phosphorus Radioisotopes: Unstable isotopes of phosphorus that decay or disintegrate emitting radiation. P atoms with atomic weights 28-34 except 31 are radioactive phosphorus isotopes.	4.87	11	0

Condition	Relationship Strength	Studies	Trials
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	4.08	15	0
2019 Novel Coronavirus Disease [description not available]	2.41	1	0
Allergic Reaction [description not available]	3.14	1	0
Hypersensitivity Altered reactivity to an antigen, which can result in pathologic reactions upon subsequent exposure to that particular antigen.	3.14	1	0
Breast Cancer [description not available]	7.38	23	0
Innate Inflammatory Response [description not available]	4.35	7	0
Breast Neoplasms Tumors or cancer of the human BREAST.	7.38	23	0
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	4.35	7	0
Encephalopathy, Toxic [description not available]	2.85	3	0
Adenocarcinoma Of Kidney [description not available]	3.73	3	0
Cancer of Kidney [description not available]	2.57	2	0
Metastase [description not available]	2.52	2	0
Carcinoma, Renal Cell A heterogeneous group of sporadic or hereditary carcinoma derived from cells of the KIDNEYS. There are several subtypes including the clear cells, the papillary, the chromophobe, the collecting duct, the spindle cells (sarcomatoid), or mixed cell-type carcinoma.	3.73	3	0
Kidney Neoplasms Tumors or cancers of the KIDNEY.	2.57	2	0
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	2.52	2	0
Disease Exacerbation [description not available]	3.87	4	0
Acute Confusional Senile Dementia [description not available]	2.25	1	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	6.73	21	0
Protein Aggregation, Pathological A biochemical phenomenon in which misfolded proteins aggregate either intra- or extracellularly. Triggered by factors such as MUTATION; POST-TRANSLATIONAL MODIFICATIONS, and environmental stress, it is generally associated with ALZHEIMER DISEASE; PARKINSON DISEASE; HUNTINGTON DISEASE; and TYPE 2 DIABETES MELLITUS.	2.25	1	0
Alzheimer Disease A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)	2.25	1	0
Benign Monoclonal Gammopathies [description not available]	2.25	1	0
Chromosome-Defective Micronuclei [description not available]	2.96	4	0
Adolescent Obesity [description not available]	2.25	1	0
Morbid Obesity [description not available]	2.25	1	0
Obesity, Morbid The condition of weighing two, three, or more times the ideal weight, so called because it is associated with many serious and life-threatening disorders. In the BODY MASS INDEX, morbid obesity is defined as having a BMI greater than 40.0 kg/m2.	2.25	1	0
Colorectal Cancer [description not available]	6.38	27	0
Colorectal Neoplasms Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.	6.38	27	0
Experimental Mammary Neoplasms [description not available]	7.64	65	0
Autosomal Dominant Juvenile Parkinson Disease [description not available]	2.25	1	0
Parkinsonian Disorders A group of disorders which feature impaired motor control characterized by bradykinesia, MUSCLE RIGIDITY; TREMOR; and postural instability. Parkinsonian diseases are generally divided into primary parkinsonism (see PARKINSON DISEASE), secondary parkinsonism (see PARKINSON DISEASE, SECONDARY) and inherited forms. These conditions are associated with dysfunction of dopaminergic or closely related motor integration neuronal pathways in the BASAL GANGLIA.	2.25	1	0
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	4.65	10	0
Colonic Diseases Pathological processes in the COLON region of the large intestine (INTESTINE, LARGE).	2.95	4	0
Cancer of Colon [description not available]	8.07	84	0
Colonic Neoplasms Tumors or cancer of the COLON.	8.07	84	0
Colitis, Mucous [description not available]	2.15	1	0
Irritable Bowel Syndrome A disorder with chronic or recurrent colonic symptoms without a clearcut etiology. This condition is characterized by chronic or recurrent ABDOMINAL PAIN, bloating, MUCUS in FECES, and an erratic disturbance of DEFECATION.	2.15	1	0
Atherosclerotic Parkinsonism [description not available]	2.17	1	0
Parkinson Disease, Secondary Conditions which feature clinical manifestations resembling primary Parkinson disease that are caused by a known or suspected condition. Examples include parkinsonism caused by vascular injury, drugs, trauma, toxin exposure, neoplasms, infections and degenerative or hereditary conditions. Clinical features may include bradykinesia, rigidity, parkinsonian gait, and masked facies. In general, tremor is less prominent in secondary parkinsonism than in the primary form. (From Joynt, Clinical Neurology, 1998, Ch38, pp39-42)	2.17	1	0
Cancer of Prostate [description not available]	7.51	29	1
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	7.51	29	1
Benign Neoplasms [description not available]	7.11	18	0
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	7.11	18	0
Adenoma, Basal Cell [description not available]	5.33	21	0
Adenoma A benign epithelial tumor with a glandular organization.	5.33	21	0
Carcinogenesis The origin, production or development of cancer through genotypic and phenotypic changes which upset the normal balance between cell proliferation and cell death. Carcinogenesis generally requires a constellation of steps, which may occur quickly or over a period of many years.	3.72	9	0
Cancer of Rectum [description not available]	2.08	1	0
Rectal Neoplasms Tumors or cancer of the RECTUM.	2.08	1	0
Cancer of Liver [description not available]	3.72	10	0
Liver Neoplasms Tumors or cancer of the LIVER.	3.72	10	0
Infections, Helicobacter [description not available]	2.08	1	0
Helicobacter Infections Infections with organisms of the genus HELICOBACTER, particularly, in humans, HELICOBACTER PYLORI. The clinical manifestations are focused in the stomach, usually the gastric mucosa and antrum, and the upper duodenum. This infection plays a major role in the pathogenesis of type B gastritis and peptic ulcer disease.	2.08	1	0
Angiogenesis, Pathologic [description not available]	2.08	1	0
Cancer, Radiation-Induced [description not available]	2.1	1	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	4.78	31	0
Cell Transformation, Neoplastic Cell changes manifested by escape from control mechanisms, increased growth potential, alterations in the cell surface, karyotypic abnormalities, morphological and biochemical deviations from the norm, and other attributes conferring the ability to invade, metastasize, and kill.	5.62	17	0
Diathesis [description not available]	3.29	6	0
Aberrant Crypt Foci Clusters of colonic crypts that appear different from the surrounding mucosa when visualized after staining. They are of interest as putative precursors to colorectal adenomas and potential biomarkers for colorectal carcinoma.	2.99	4	0
Obesity A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).	2.52	2	0
E coli Infections [description not available]	2.11	1	0
Acute Bacterial Prostatitis [description not available]	2.11	1	0
Escherichia coli Infections Infections with bacteria of the species ESCHERICHIA COLI.	2.11	1	0
Prostatitis Infiltration of inflammatory cells into the parenchyma of PROSTATE. The subtypes are classified by their varied laboratory analysis, clinical presentation and response to treatment.	2.11	1	0
Chronic Illness [description not available]	2.13	1	0
Chronic Disease Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).	2.13	1	0
Colitis Inflammation of the COLON section of the large intestine (INTESTINE, LARGE), usually with symptoms such as DIARRHEA (often with blood and mucus), ABDOMINAL PAIN, and FEVER.	3.16	5	0
Cancer of Intestines [description not available]	4.68	28	0
Intestinal Neoplasms Tumors or cancer of the INTESTINES.	4.68	28	0
Weight Gain Increase in BODY WEIGHT over existing weight.	2.44	2	0
Genetic Predisposition [description not available]	6.9	11	1
Intraepithelial Prostatic Neoplasia [description not available]	3.14	5	0
Prostatic Intraepithelial Neoplasia A premalignant change arising in the prostatic epithelium, regarded as the most important and most likely precursor of prostatic adenocarcinoma. The neoplasia takes the form of an intra-acinar or ductal proliferation of secretory cells with unequivocal nuclear anaplasia, which corresponds to nuclear grade 2 and 3 invasive prostate cancer.	3.14	5	0
Chromosomal Instability An increased tendency to acquire CHROMOSOME ABERRATIONS when various processes involved in chromosome replication, repair, or segregation are dysfunctional.	2.13	1	0
Abnormalities, Autosome [description not available]	3.26	6	0
Carcinoma, Epidermoid [description not available]	2.45	2	0
Cancer of Skin [description not available]	2.15	1	0
Invasiveness, Neoplasm [description not available]	2.74	3	0
Carcinoma, Squamous Cell A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed)	2.45	2	0
Skin Neoplasms Tumors or cancer of the SKIN.	2.15	1	0
Cancer of Lung [description not available]	2.92	4	0
Lung Neoplasms Tumors or cancer of the LUNG.	2.92	4	0
Adenocarcinoma, Basal Cell [description not available]	5.75	33	0
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	5.75	33	0
Cancer of Stomach [description not available]	3.1	5	0
Stomach Neoplasms Tumors or cancer of the STOMACH.	3.1	5	0
Hepatocellular Carcinoma [description not available]	3.1	5	0
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	3.1	5	0
Condition, Preneoplastic [description not available]	4.77	31	0
Precancerous Conditions Pathological conditions that tend eventually to become malignant.	4.77	31	0
Genome Instability [description not available]	2.48	2	0
Choriocarcinoma A malignant metastatic form of trophoblastic tumors. Unlike the HYDATIDIFORM MOLE, choriocarcinoma contains no CHORIONIC VILLI but rather sheets of undifferentiated cytotrophoblasts and syncytiotrophoblasts (TROPHOBLASTS). It is characterized by the large amounts of CHORIONIC GONADOTROPIN produced. Tissue origins can be determined by DNA analyses: placental (fetal) origin or non-placental origin (CHORIOCARCINOMA, NON-GESTATIONAL).	2.07	1	0
Experimental Neoplasms [description not available]	4.14	16	0
Cancer of Pancreas [description not available]	3.25	6	0
Pancreatic Neoplasms Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).	3.25	6	0
Carcinoma, Anaplastic [description not available]	2.92	4	0
Carcinoma A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.	2.92	4	0
Polyps Discrete abnormal tissue masses that protrude into the lumen of the DIGESTIVE TRACT or the RESPIRATORY TRACT. Polyps can be spheroidal, hemispheroidal, or irregular mound-shaped structures attached to the MUCOUS MEMBRANE of the lumen wall either by a stalk, pedunculus, or by a broad base.	2.01	1	0
Complications, Pregnancy [description not available]	2.01	1	0
Experimental Hepatoma [description not available]	3.78	11	0
Cocarcinogenesis The combination of two or more different factors in the production of cancer.	3.87	12	0
Animal Mammary Carcinoma [description not available]	5.1	10	0
Cancer of the Tongue [description not available]	2.01	1	0
Tongue Neoplasms Tumors or cancer of the TONGUE.	2.01	1	0
A-Thalassemia [description not available]	2.42	2	0
Anemia, Cooley's [description not available]	2.42	2	0
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	0
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	0
Bile Duct Obstruction [description not available]	2.02	1	0
Cholestasis Impairment of bile flow due to obstruction in small bile ducts (INTRAHEPATIC CHOLESTASIS) or obstruction in large bile ducts (EXTRAHEPATIC CHOLESTASIS).	2.02	1	0
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	2.91	4	0
Biliary Cirrhosis [description not available]	2.02	1	0
Liver Cirrhosis, Biliary FIBROSIS of the hepatic parenchyma due to obstruction of BILE flow (CHOLESTASIS) in the intrahepatic or extrahepatic bile ducts (BILE DUCTS, INTRAHEPATIC; BILE DUCTS, EXTRAHEPATIC). Primary biliary cholangitis involves the destruction of small intra-hepatic bile ducts and decreased bile secretion. Secondary biliary cholangitis is produced by prolonged obstruction of large intrahepatic or extrahepatic bile ducts from a variety of causes.	2.02	1	0
Adenomatous Polyposis Coli, Familial [description not available]	2.44	2	0
Adenomatous Polyposis Coli A polyposis syndrome due to an autosomal dominant mutation of the APC genes (GENES, APC) on CHROMOSOME 5. The syndrome is characterized by the development of hundreds of ADENOMATOUS POLYPS in the COLON and RECTUM of affected individuals by early adulthood.	2.44	2	0
Multiple Neurofibromas [description not available]	2.02	1	0
Neurofibromatoses A group of disorders characterized by an autosomal dominant pattern of inheritance with high rates of spontaneous mutation and multiple neurofibromas or neurilemmomas. NEUROFIBROMATOSIS 1 (generalized neurofibromatosis) accounts for approximately 95% of cases, although multiple additional subtypes (e.g., NEUROFIBROMATOSIS 2, neurofibromatosis 3, etc.) have been described. (From Neurochirurgie 1998 Nov;44(4):267-72)	2.02	1	0
Metaplasia A condition in which there is a change of one adult cell type to another similar adult cell type.	2.02	1	0
Signet Ring Cell Carcinoma [description not available]	2.02	1	0
Carcinoma, Signet Ring Cell A poorly differentiated adenocarcinoma in which the nucleus is pressed to one side by a cytoplasmic droplet of mucus. It usually arises in the gastrointestinal system.	2.02	1	0
Hematologic Malignancies [description not available]	2.41	2	0
Hematologic Neoplasms Neoplasms located in the blood and blood-forming tissue (the bone marrow and lymphatic tissue). The commonest forms are the various types of LEUKEMIA, of LYMPHOMA, and of the progressive, life-threatening forms of the MYELODYSPLASTIC SYNDROMES.	2.41	2	0
Chromosomal Breakage [description not available]	2.03	1	0
Atrophy Decrease in the size of a cell, tissue, organ, or multiple organs, associated with a variety of pathological conditions such as abnormal cellular changes, ischemia, malnutrition, or hormonal changes.	2.03	1	0
Hyperlipemia [description not available]	2.95	1	0
Alcohol Drinking Behaviors associated with the ingesting of ALCOHOLIC BEVERAGES, including social drinking.	2.95	1	0
Hyperlipidemias Conditions with excess LIPIDS in the blood.	2.95	1	0
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)	2.68	3	0
Cataract, Membranous [description not available]	1.98	1	0
Cataract Partial or complete opacity on or in the lens or capsule of one or both eyes, impairing vision or causing blindness. The many kinds of cataract are classified by their morphology (size, shape, location) or etiology (cause and time of occurrence). (Dorland, 27th ed)	1.98	1	0
Fibrosarcoma A sarcoma derived from deep fibrous tissue, characterized by bundles of immature proliferating fibroblasts with variable collagen formation, which tends to invade locally and metastasize by the bloodstream. (Stedman, 25th ed)	1.98	1	0
Intestinal Polyps Discrete abnormal tissue masses that protrude into the lumen of the INTESTINE. A polyp is attached to the intestinal wall either by a stalk, pedunculus, or by a broad base.	1.99	1	0
Germinoblastoma [description not available]	3.49	8	0
Lymphoma A general term for various neoplastic diseases of the lymphoid tissue.	3.49	8	0
Bladder Cancer [description not available]	1.98	1	0
Urinary Bladder Neoplasms Tumors or cancer of the URINARY BLADDER.	1.98	1	0
Cirrhosis [description not available]	1.98	1	0
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	1.98	1	0
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	1.98	1	0
Adenoma, Prostatic [description not available]	2.4	2	0
Prostatic Hyperplasia Increase in constituent cells in the PROSTATE, leading to enlargement of the organ (hypertrophy) and adverse impact on the lower urinary tract function. This can be caused by increased rate of cell proliferation, reduced rate of cell death, or both.	2.4	2	0
Papilloma, Intraductal A small, often impalpable benign papilloma arising in a lactiferous duct and frequently causing bleeding from the nipple. (Stedman, 25th ed)	1.99	1	0
Neoplasm Metastasis, Unknown Primary [description not available]	1.99	1	0
Colon Cancer, Familial Nonpolyposis [description not available]	2	1	0
Colorectal Neoplasms, Hereditary Nonpolyposis A group of autosomal-dominant inherited diseases in which COLON CANCER arises in discrete adenomas. Unlike FAMILIAL POLYPOSIS COLI with hundreds of polyps, hereditary nonpolyposis colorectal neoplasms occur much later, in the fourth and fifth decades. HNPCC has been associated with germline mutations in mismatch repair (MMR) genes. It has been subdivided into Lynch syndrome I or site-specific colonic cancer, and LYNCH SYNDROME II which includes extracolonic cancer.	2	1	0
Arteriosclerosis Thickening and loss of elasticity of the walls of ARTERIES of all sizes. There are many forms classified by the types of lesions and arteries involved, such as ATHEROSCLEROSIS with fatty lesions in the ARTERIAL INTIMA of medium and large muscular arteries.	2	1	0
Hypertriglyceridemia A condition of elevated levels of TRIGLYCERIDES in the blood.	2	1	0
Carcinoma, Oat Cell [description not available]	2	1	0
Carcinoma, Small Cell An anaplastic, highly malignant, and usually bronchogenic carcinoma composed of small ovoid cells with scanty neoplasm. It is characterized by a dominant, deeply basophilic nucleus, and absent or indistinct nucleoli. (From Stedman, 25th ed; Holland et al., Cancer Medicine, 3d ed, p1286-7)	2	1	0
Aberrant Tissue [description not available]	2	1	0
Carcinoma, Colloid [description not available]	2	1	0
Cancer of Jejunum [description not available]	2	1	0
Adenocarcinoma, Mucinous An adenocarcinoma producing mucin in significant amounts. (From Dorland, 27th ed)	2	1	0
Hyperplasia An increase in the number of cells in a tissue or organ without tumor formation. It differs from HYPERTROPHY, which is an increase in bulk without an increase in the number of cells.	2.94	4	0
Cancer of Duodenum [description not available]	2.01	1	0
B-Cell Lymphoma [description not available]	2.01	1	0
Lymphoma, B-Cell A group of heterogeneous lymphoid tumors generally expressing one or more B-cell antigens or representing malignant transformations of B-lymphocytes.	2.01	1	0
Cancer of Gastrointestinal Tract [description not available]	2.07	1	0

2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine

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