benzo(a)pyrene profile

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. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

benzo[a]pyrene : An ortho- and peri-fused polycyclic arene consisting of five fused benzene rings. [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	2336
CHEMBL ID	31184
CHEBI ID	29865
MeSH ID	M0002349

Synonym
BIDD:ER0497
BRD-K09668667-001-02-0
benzo[def]chrysene
CHEBI:29865 ,
benzo[pqr]tetraphene
(b(a)p)
benzo(a)pyrene
3,4-benzopirene
benz[a]pyrene
3,4-benzopyrene
3,4-benz[a]pyrene
nsc-21914
BP ,
3,4-benzpyrene
3,4-benzpyren
nsc21914
3,4-benzypyrene
benzo[d,f]chrysene
3,4-bp
wln: l d6 b6666 2ab tj
b[a]p
6,7-benzopyrene
3,4-benzopyrene (carcinogen)
DIVK1C_007049
NCI60_001824
3,4-benzylpyrene
benzo[d,e,f]chrysene
ai3-50461
einecs 200-028-5
rcra waste no. u022
b(a)p
benzo(def)chrysene
nsc 21914
3,4-benz(a)pyrene
coal tar pitch volatiles: benzo(a)pyrene
3,4-benzo(a)pyrene
ccris 76
3,4-benzopirene [italian]
hsdb 2554
benz(a)pyrene
benzo(d,e,f)chrysene
3,4-benzpyren [german]
rcra waste number u022
SPECTRUM_001871
SPECTRUM5_001824
50-32-8
benzpyrene
C07535
benzo[a]pyrene
benzo[a]pyrene, >=96% (hplc)
benzo[a]pyrene, analytical standard, for environmental analysis
KBIO3_002470
KBIOGR_001138
KBIO2_004953
KBIO1_001993
KBIOSS_002390
KBIO2_002385
KBIO2_007521
SPECTRUM2_001081
SPECPLUS_000953
SPECTRUM4_000609
SPECTRUM3_001695
SPBIO_001122
benzo[a]pyrene (bap)
BSPBIO_003250
NCGC00178185-01
3,4 benzpyrene
3,4 benzopyrene
B0085
MLS002695983
smr000393676
bdbm50137506
benzo[a]-pyrene
CHEMBL31184 ,
NCGC00178185-02
benzo(a)pyrene, radical ion(1-)
34505-58-3
HMS3089C04
tox21_200710
NCGC00258264-01
cas-50-32-8
dtxsid2020139 ,
dtxcid40139
A828066
A828067
6699-27-0
benzo(a)pyrene radical cation
benzo(3,4)pyrene, radical ion(1+)
benzo(a)pyrene, labeled with tritium
42299-33-2
benzo(a)pyrene, radical ion(1+)
CCG-39759
unii-3417wma06d
3417wma06d ,
FT-0614185
EPITOPE ID:117721
AKOS015907666
benzo(a)pyrene [iarc]
benzo(a)pyrene [hsdb]
benzo(a)pyrene [mi]
AM61580
benzo pyrene[bap]
CS-7789
mfcd00003602
benzo[a]pyrene, certified reference material, tracecert(r)
benzo[a]pyrene, vial of 1 g, analytical standard
benzo[a]pyrene 100 microg/ml in cyclohexane
benzo[a]pyrene 100 microg/ml in acetonitrile
benzo[a]pyrene 10 microg/ml in acetonitrile
HY-107377
Q306051
SY048151
3,4-benzopyrene (purified by sublimation)
HMS3746C17
benzo[a]pyrene 1000 microg/ml in acetone
52 - low level cip2 contaminants
benzo(a)pyrene-7 8-d2 98
benzopireno
benzo(a)pyrene (iarc)
6,7-benzpyren
benzo(pqr)tetraphene
3,4-benzpyrene (carcinogen)

Excerpt	Reference	Relevance
"0 mmol/kg) alone were toxic to mice induced with benzo(a)pyrene but not to control or phenobarbitone-induced mice."	( Cysteine isopropylester protects against paracetamol-induced toxicity. Butterworth, M; Cohen, GM; Smith, LL; Upshall, DG, 1992)	0.54
" 7,12-Dimethylbenz(a)anthracene (DMBA) and 7-hydroxymethyl-12-methylbenz(a)anthracene (7-OHM-12-MBA), but not benzo(a)pyrene (BP), selectively produce necrosis in the two inner zones of the rat adrenal cortex and are toxic to cultured rat adrenocortical cells."	( Influence of effectors of prostaglandin metabolism on the toxicity induced by 7-hydroxymethyl-12-methylbenz(a)anthracene in cultured rat adrenal cells. Hallberg, E; Rydström, J, 1990)	0.49
" These experiments suggest that toxic effects to one ovary may result in compensatory hypertrophy of the contralateral ovary."	( Ovarian toxicity of benzo(a)pyrene and metabolites in mice. Mattison, DR; Singh, H; Takizawa, K; Thomford, PJ, 1989)	0.6
" Analysis of the bone marrow and peripheral blood changes showed that severe toxic chemical bone marrow depression in D2 mice by continued oral BaP cannot serve as an experimental model system of acute aplastic anemia."	( Acute hematotoxicity of oral benzo(a)pyrene: the role of the Ah locus. Anselstetter, V; Heimpel, H, 1986)	0.56
" GSH inhibited the mutagenicity at low (essentially non-lethal) concentrations of BP-diol, but did not do so at toxic concentrations."	( Modulation of the cytotoxicity and mutagenicity of benzo[a]pyrene and benzo[a]pyrene 7,8-diol by glutathione and glutathione S-transferases in mammalian cells (CHO/HGPRT assay). Hsie, AW; Recio, L, 1987)	0.27
"Serially cultivated keratinocytes of human and rat epidermis and esophagus were compared with respect to their sensitivity to toxic effects of 3-methylcholanthrene and ability to metabolize benzo(a)pyrene."	( Polycyclic aromatic hydrocarbon toxicity and induction of metabolism in cultivated esophageal and epidermal keratinocytes. Heimann, R; Rice, RH, 1983)	0.46
"A strain of rat liver epithelial cells (LP), a clone of LP (C3) and a series of transformed lines derived from these cell strains, were examined for their sensitivity to the toxic effects of benzo[a]pyrene (BP)."	( Sensitivity of normal and transformed rat liver epithelial cells to benzo[a]pyrene toxicity. Paraskeva, C; Parkinson, EK, 1981)	0.26
"Study in cell cultures of toxic action and metabolism of benz(a)pyrene and its derivatives substituted in the 6th position has shown that the toxic effect of the compounds depends on the substituent moiety."	( [Mechanisms of the toxic effect of benz(a)pyrene and its derivatives in tissue culture]. Belitskiĭ, GA; Khitrovo, IA; Kobliakov, VA, 1981)	0.26
" The toxic effects of benzo[a]pyrene (BP) and 7,12-dimethylbenz[a]anthracene (DMBA) were studied in these two cell lines."	( Cytotoxic effects and metabolism of benzo[a]pyrene and 7,12-dimethylbenz[a]anthracene in duodenal and ileal epithelial cell cultures. Isselbacher, KJ; Quaroni, A, 1981)	0.26
" No differences were observed in the toxic effects of methylnitrosourea, a carcinogen that does not need metabolic activation, on normal and variant fibroblasts."	( Effect of glucose-6-phosphate dehydrogenase deficiency on the benz(a)pyrene toxicity for in vitro cultured human skin fibroblasts. Daino, L; Feo, F; Frassetto, S; Garcea, R; Gaspa, L; La Spina, V; Ledda, GM; Pascale, R; Pirisi, L; Zanetti, S, 1982)	0.26
" Presence of the high-affinity receptor leads to greater cytochrome P1-450 induction by benzo[a]pyrene; in turn, enhanced benzo[a]pyrene metabolism can result in more toxic intermediates or greater detoxication, depending upon the test system studied."	( Bone marrow toxicity induced by oral benzo[a]pyrene: protection resides at the level of the intestine and liver. Harrison, DE; Legraverend, C; Nebert, DW; Ruscetti, FW, 1983)	0.27
" More toxic metabolites (especially benzo[a]pyrene 1,6- and 3,6-quinones) are shown to occur in Ahd/Ahd embryos than in Ahb/Ahd embryos."	( Importance of the route of administration for genetic differences in benzo[a]pyrene-induced in utero toxicity and teratogenicity. Guenthner, TM; Legraverend, C; Nebert, DW, 1984)	0.27
" In contrast, no difference between the normal and the deficient fibroblasts exists as regards the toxic effect of methylnitrosourea, a carcinogen that does not need metabolic activation."	( Modulatory effect of glucose-6-phosphate dehydrogenase deficiency on benzo(a)pyrene toxicity and transforming activity for in vitro-cultured human skin fibroblasts. Daino, L; Feo, F; Frassetto, S; Garcea, R; Gaspa, L; Pascale, R; Pirisi, L, 1984)	0.5
" gigas larva test showed the clastogenic action of BaP and the toxic effect of cupric sulfate on culture cells as well as the slighter toxic effect of paper mill effluent on spats."	( The micronucleus assay in Crassostrea gigas for the detection of seawater genotoxicity. Burgeot, T; Galgani, F; His, E, 1995)	0.29
"5 ppb) had no toxic effects on the larvae."	( Effects of light on the cytotoxicity and genotoxicity of benzo(a)pyrene and an oil refinery effluent in the newt. Fernandez, M; l'Haridon, J, 1994)	0.53
"The authors previously demonstrated that simulated solar radiation (SSR), with a fluence rate of only 40 mumol m-2 sec-1, increased polycyclic aromatic hydrocarbon (PAH) toxicity to the duckweed Lemna gibba and that PAHs photomodified in SSR (generally oxygenation of the ring system) are more toxic than the parent compounds (Huang et al."	( Increased polycyclic aromatic hydrocarbon toxicity following their photomodification in natural sunlight: impacts on the duckweed Lemna gibba L. G-3. Dixon, DG; Greenberg, BM; Huang, XD, 1995)	0.29
"The association of small quantities of ferric oxide with Benzo[a]Pyrene (BaP) appears to increase in vivo the toxic effect of BaP."	( Toxicity of ferric oxide and benzo[a]pyrene alone or in combination in respiratory tract of Sprague Dawley rats. Balduyck, M; Boutin, AC; Gosset, P; Haguenoer, JM; Huet, G; Marez, T; Shirali, P; Venembre, P, 1996)	0.29
" Later on, we have studied toxic effects of iron oxides (Hematite Fe2O3 and Magnetite Fe3O4), benzo[a]pyrene (BaP) and Pyrene, alone or in combination."	( Toxicity of iron oxides and metabolites of benzo[a]pyrene alone or in combination in cells culture and identification by laser microprobe mass spectrometry. Boutin, AC; Gosset, P; Hachimi, A; Haguenoer, JM; Marez, T; Maunit, B; Muller, JF; Shirali, P, 1996)	0.29
" However, the net effect was still for AHA to ameliorate PAH photo-induced toxicity even though UV has the potential to photooxidize AHA and enhance the production of potentially toxic reactive oxygen species from AHA photosensitization."	( Amelioration of the photo-induced toxicity of polycyclic aromatic hydrocarbons by a commercial humic acid. Dixon, DG; Gensemer, RW; Greenberg, BM, 1998)	0.3
" Most toxic effects were only observed in the highest-dose group (90 mg/kg), but compared to the general toxicity, some parameters indicating immunotoxic effects were also affected at lower doses (10 and 30 mg/kg)."	( Detection of immunotoxicity of benzo[a]pyrene in a subacute toxicity study after oral exposure in rats. De Jong, WH; Kroese, ED; Van Loveren, H; Vos, JG, 1999)	0.3
" The guinea pig is the most susceptible mammal known, with an LD50 in the range 1-2 micrograms TCDD/kg, whereas the hamster is the most resistant species with an LD50 greater than 3000 micrograms/kg."	( Interspecies differences in cancer susceptibility and toxicity. Hengstler, JG; Oesch, F; Steinberg, P; Van der Burg, B, 1999)	0.3
" These data suggest that UGT1A7 may be preferentially active toward B[a]P-quinones and that UGT1A7 may represent the PAH-inducible UGT activity previously implicated in protection against toxic redox cycling by B[a]P-3,6-quinone."	( Differential protection by rat UDP-glucuronosyltransferase 1A7 against Benzo[a]pyrene-3,6-quinone- versus Benzo[a]pyrene-induced cytotoxic effects in human lymphoblastoid cells. Crespi, CL; Grove, AD; Kessler, FK; Llewellyn, GC; Ritter, JK; White, KL, 2000)	0.31
" Although a single 500 mg/kg dose of BaP was toxic to Cyp1a1(+/-) mice (serum liver enzyme elevated about 2-fold above control levels at 48 h), Cyp1a1(-/-) mice displayed no hepatotoxicity."	( Benzo[a]pyrene-induced toxicity: paradoxical protection in Cyp1a1(-/-) knockout mice having increased hepatic BaP-DNA adduct levels. Dalton, TP; Genter, MB; Nebert, DW; Shertzer, HG; Talaska, G; Uno, S; Warshawsky, D, 2001)	0.31
" These complexes were tested on benzo(a)pyrene-induced tumours in Wistar rats to detect their antitumour and toxic effects."	( Antitumour and toxic effects on Wistar rats of two new platinum complexes. Agnantis, N; Charalabopoulos, K; Evangelou, A; Hadjiliadis, N; Ioachim, E; Karkabounas, S; Papalimneou, V; Syrigos, K, 2002)	0.6
" Toxic effects included a decrease in leucocyte cell count, mild haemolysis, mild haematuria, mild hepatotoxicity, elevated body temperature and hair loss."	( Antitumour and toxic effects on Wistar rats of two new platinum complexes. Agnantis, N; Charalabopoulos, K; Evangelou, A; Hadjiliadis, N; Ioachim, E; Karkabounas, S; Papalimneou, V; Syrigos, K, 2002)	0.31
" The polycyclic aromatic hydrocarbons (PAHs) were not highly toxic to either bacterial strain; the toxicity of their degradation products depended on the method of chemical processing."	( Microbiological evaluation of toxicity of three polycyclic aromatic hydrocarbons and their decomposition products formed by advanced oxidation processes. Jamroz, T; Ledakowicz, S; Miller, JS; Sencio, B, 2003)	0.32
" In congenic mice with a low affinity AhR (AhR(d)), DMBA and BP are equally toxic to the BM whereas AhR(d) x CYP1B1-null mice are fully protected."	( Bone marrow cytotoxicity of benzo[a]pyrene is dependent on CYP1B1 but is diminished by Ah receptor-mediated induction of CYP1A1 in liver. Czuprynski, CJ; Galván, N; Jaskula-Sztul, R; Jefcoate, CR; MacWilliams, PS, 2003)	0.32
" It was found that both Caco-2 and Hep G2 cells can metabolize B[a]P to toxic metabolites including B[a]P-7,8-hydrodiol (7,8-diol), an immediate precursor to the highly-reactive ultimate toxicant of B[a]P, B[a]P-7,8-hydrodiol-9,10-epoxide (BPDE), possibly mediated by cytochrome P450 1A1/2 activity."	( Feasibility of a simple double-layered coculture system incorporating metabolic processes of the intestine and liver tissue: application to the analysis of benzo[a]pyrene toxicity. Choi, S; Nishikawa, M; Sakai, Y; Sakoda, A, 2004)	0.32
" This study investigated whether HC modulates cigarette carcinogen benzo[a]pyrene (B[a]P)-mediated toxic effects."	( Hydroxychavicol modulates benzo[a]pyrene-induced genotoxicity through induction of dihydrodiol dehydrogenase. Chang, KW; Chi, CW; Liu, TY; Tang, DW, 2004)	0.32
" A "relative risk index" (RRI) was developed to account for the combined effects of compound-specific bioavailability and toxic potency in estimating excess cancer risk."	( Combined effects of contaminant desorption and toxicity on risk from PAH contaminated sediments. Kosson, DS; Rockne, KJ; Shor, LM; Taghon, GL; Young, LY, 2004)	0.32
" The report of a positive correlation between human plasma B[a]P levels and body mass index, together with B[a]P's lipophilicity, led us to test for possible adverse effects of B[a]P on adipose tissue."	( Benzo[a]pyrene impairs beta-adrenergic stimulation of adipose tissue lipolysis and causes weight gain in mice. A novel molecular mechanism of toxicity for a common food pollutant. Bihain, BE; Irigaray, P; Jacquenet, S; Méjean, L; Notet, V; Ogier, V; Sibille, P; Yen, FT, 2006)	0.33
" Studies have established that B(a)P requires metabolic activation to highly reactive species to elicit many of its adverse effects."	( Benzo(a)pyrene-induced acute neurotoxicity in the F-344 rat: role of oxidative stress. Das, SK; Mukherjee, S; Ramesh, A; Saunders, CR; Shockley, DC, )	1.57
" The immune system can be a target for many chemicals including environmental contaminants and drugs with potential adverse effects on human health."	( In vitro tests to evaluate immunotoxicity: a preliminary study. Carfi', M; Corsini, E; Gennari, A; Gribaldo, L; Hartung, T; Malerba, I; Pallardy, M; Pieters, R; Van Loveren, H; Vohr, HW, 2007)	0.34
" Toxic potency assessment of soil PAHs presented a good relationship with benzo(a)pyrene (BaP) levels, toxic equivalent concentrations based on BaP (TEQ(BaP)) and dioxin-like toxic equivalent concentrations (TEQ(TCDD))."	( Polycyclic aromatic hydrocarbons in Dalian soils: distribution and toxicity assessment. Chen, J; Qiao, X; Tian, F; Wang, Z; Yang, P, 2007)	0.57
"Genotoxicity biomarkers are widely measured in ecotoxicology as molecular toxic endpoints of major environmental pollutants."	( Investigating the relationship between embryotoxic and genotoxic effects of benzo[a]pyrene, 17alpha-ethinylestradiol and endosulfan on Crassostrea gigas embryos. Akcha, F; Caisey, X; Quiniou, F; Rousseau, S; Wessel, N, 2007)	0.34
"A novel sediment-contact assay using embryos of the transgenic medaka was developed to fully characterize the toxic effects induced by exposure to a mixture of organic pollutants in sediments."	( Characterization of toxic effects of sediment-associated organic pollutants using the lambda transgenic medaka. Budzinski, H; Cachot, J; Law, M; Norris, M; Peluhet, L; Pottier, D; Winn, R, 2007)	0.34
" PBO alone was not particularly toxic to grass shrimp larvae."	( Piperonyl butoxide enhances the bioconcentration and photoinduced toxicity of fluoranthene and benzo[a]pyrene to larvae of the grass shrimp (Palaemonetes pugio). Garner, TR; Weinstein, JE, 2008)	0.35
" These results suggest that immature plum extracts may counteract toxic effects of carcinogens, such as B(alpha)P, and therefore possess the chemopreventive efficacy."	( Inhibitory effects of methanol extract of plum (Prunus salicina L., cv. 'Soldam') fruits against benzo(alpha)pyrene-induced toxicity in mice. Kim, HJ; Lee, IS; Yu, MH, 2008)	0.35
" CYP1A1-inducible chemicals, such as benzo[a]pyrene and 2,3,7,8-tetrachlorodibenzo-p-dioxin, are known to have adverse effects (i."	( Omeprazole alleviates benzo[a]pyrene cytotoxicity by inhibition of CYP1A1 activity in human and mouse hepatoma cells. Kawanishi, M; Ohsako, S; Shiizaki, K; Yagi, T, 2008)	0.35
"A bioassay was developed to assess the toxic effects of ingested prey contaminated by polycyclic aromatic hydrocarbons (PAHs) using the teleost Fundulus heteroclitus as a predator and the polychaete Nereis virens as a benthic vector."	( A fish bioassay to evaluate the toxicity associated with the ingestion of benzo[a]pyrene-contaminated benthic prey. Couillard, CM; Laplatte, B; Pelletier, E, 2009)	0.35
"The present study is the first in a series reporting on in vitro toxic potencies of oils."	( Specific in vitro toxicity of crude and refined petroleum products. 1. Aryl hydrocarbon receptor-mediated responses. Jonker, MT; Murk, AJ; Vrabie, CM, 2009)	0.35
" However, the toxic effects and related mechanism of co-exposure to BaP and PCB126 remain unknown."	( PCB126 enhanced the genotoxicity of BaP in HepG2 cells by modulating metabolic enzyme and DNA repair activities. Chen, XM; Liu, AL; Lu, WQ; Wei, W; Xie, SH; Zhang, C, 2009)	0.35
" While these compounds are primarily known for their carcinogenicity, B[a]P and its metabolites are also toxic for mammalian immune cells."	( Modulation of benzo[a]pyrene induced immunotoxicity in mice actively immunized with a B[a]P-diphtheria toxoid conjugate. Farinelle, S; Grova, N; Muller, CP; Prodhomme, EJ; Schellenberger, MT; Willième, S, 2009)	0.35
" The toxicity of PAHs mixtures can be characterized more accurately by developing and establishing toxic equivalency factors (TEFs) for PAHs."	( Distribution of polycyclic aromatic hydrocarbons in marine sediments and their potential toxic effects. Da Luz, EC; Froehner, S; Maceno, M; Machado, KS; Souza, DB, 2010)	0.36
" Altogether, our data emphasize that (i) a combination of analytical approaches is required to assess the genotoxicity of complex mixtures and (ii) risk assessment based on additivity consideration such as toxic equivalent factors may be misleading."	( Relative contribution of DNA strand breaks and DNA adducts to the genotoxicity of benzo[a]pyrene as a pure compound and in complex mixtures. Douki, T; Lefebvre, E; Maitre, A; Marie, C; Marques, M; Ravanat, JL; Tarantini, A, 2009)	0.35
"Polycyclic aromatic hydrocarbons (PAHs) are ubiquitous environmental contaminants with various toxic effects including immune suppression."	( Identification of AhR-regulated genes involved in PAH-induced immunotoxicity using a highly-sensitive DNA chip, 3D-Gene Human Immunity and Metabolic Syndrome 9k. Hashimoto, H; Ichikawa, M; Iwano, S; Miyamoto, Y; Takizawa, S, 2010)	0.36
" The ADP1_recA_lux was used to detect a variety of toxic or potentially toxic compounds including mitomycin C (MMC), methyl methanesulfonate, ethidium bromide, H2O2, toluene, single-wall nanocarbon tubes (SWNCT), nano Au colloids (20 nm), pyrene, beno[a]pyrene, and UV light."	( Optimization of bacterial whole cell bioreporters for toxicity assay of environmental samples. Banwart, SA; Huang, WE; Lerner, DN; Li, G; Song, Y; Thompson, IP; Thornton, SF, 2009)	0.35
" The carcinogenicity of the pitches, evaluated on the basis of benzo[a]pyrene toxic equivalency factors, also followed the same tendency."	( Preparation of low toxicity pitches by thermal oxidative condensation of anthracene oil. Alvarez, P; Blanco, C; Granda, M; José Fernández, J; Menéndez, R; Santamaría, R; Sutil, J; Viña, JA, 2009)	0.35
"Although, heavy metals and polycyclic aromatic hydrocarbons (PAHs) have been reported at high levels in marine mammals, little is known about the toxic effects of some of these contaminants."	( Toxic effects of various pollutants in 11B7501 lymphoma B cell line from harbour seal (Phoca vitulina). Fortier, M; Fournier, M; Frouin, H, 2010)	0.36
" Adverse effects of B(a)P were tested by cytokinesis-block micronucleus (CBMN) cytome assays."	( [Cytotoxicity and genomic damage of benzo[a]pyrene in gene transformed cell model]. Bin, P; Chen, W; Dai, YF; Duan, HW; Liu, Q; Liu, QJ; Niu, Y; Wang, YD; Zheng, YX, 2010)	0.36
" Significant adverse effects were observed on the reproductive system, including decreased sperm count, increased production of abnormal sperm, changes in serum testosterone levels and irregular arrangements of the seminiferous epithelium."	( The combined toxicity of dibutyl phthalate and benzo(a)pyrene on the reproductive system of male Sprague Dawley rats in vivo. An, H; Ao, L; Cao, J; Chen, X; Liu, W; Sun, L; Wang, Y; Zhou, Z, 2011)	0.63
" Our findings demonstrate that the two OPP parent chemicals and IMP degradate can mediate a number of toxic effects or cellular alterations at very low concentrations."	( Sublethal genotoxicity and cell alterations by organophosphorus pesticides in MCF-7 cells: implications for environmentally relevant concentrations. Halsall, CJ; Llabjani, V; Martin, FL; Ukpebor, J, 2011)	0.37
" It is concluded that exposure to BaP may exert adverse effects on the immune system of broilers which may increase their susceptibility to disease, and Ns supplementation significantly reduces these alterations."	( Efficacy of Nigella sativa in alleviating benzo[a]pyrene-induced immunotoxicity in broilers. Karim, AJ; Latif, IK; Niu, JP; Noordin, MM; Zamri-Saad, M; Zuki, AB, 2011)	0.37
" However, the existing data on their toxic effects in vitro and/or in vivo are still largely incomplete."	( Toxic effects of methylated benzo[a]pyrenes in rat liver stem-like cells. Ciganek, M; Hulinková, P; Krčková, S; Krčmář, P; Machala, M; Marvanová, S; Milcová, A; Neča, J; Pálková, L; Pĕnčíková, K; Topinka, J; Trilecová, L; Vondráček, J, 2011)	0.37
"To gain insight into the toxic effects of the carcinogenic PAH benzo[a]pyrene (BaP) on the typical marine benthic polychaete Perinereis nuntia, we amplified and sequenced genes by creating subtractive cDNA libraries between worms exposed to BaP and solvent control."	( Toxicity evaluation of benzo[a]pyrene on the polychaete Perinereis nuntia using subtractive cDNA libraries. Bian, M; Chen, B; Huang, H; Lin, K; Liu, Z; Qiu, X; Yu, W; Yu, X; Zheng, S, 2011)	0.37
" (±)-anti-BPDE and B[a]P-7,8-trans-dihydrodiol, an intermediate in (±)-anti-BPDE metabolism, are toxic to A549 cells at concentrations with an IC(50) of ∼2 μM."	( Aldo-keto reductases protect lung adenocarcinoma cells from the acute toxicity of B[a]P-7,8-trans-dihydrodiol. Abedin, Z; Field, J; Sen, S, 2012)	0.38
" Embryo toxic responses showed a clear dose-related tendency whereas no clear dose-dependent effect was observed in micronucleus induction."	( Linking embryo toxicity with genotoxic responses in the freshwater snail Physa acuta: single exposure to benzo(a)pyrene, fluoxetine, bisphenol A, vinclozolin and exposure to binary mixtures with benzo(a)pyrene. Aparicio, N; Fernández, C; Sánchez-Argüello, P, 2012)	0.59
" Exposure to BaP elicits many adverse biological effects, including tumor formation, immunosuppression, teratogenicity, and hormonal effects."	( Review on proteomic analyses of benzo[a]pyrene toxicity. Pink, M; Rettenmeier, AW; Schmitz-Spanke, S; Verma, N, 2012)	0.38
" Aroclor1254 was more toxic than Bap to embryos and larvae."	( Toxic effects of benzo[a]pyrene (Bap) and Aroclor1254 on embryogenesis, larval growth, survival and metamorphosis of the bivalve Meretrix meretrix. Liu, B; Wang, Q; Wang, X; Yang, H, 2012)	0.38
" However, different toxic effects were observed for the combined exposure to PAHs and phytoestrogen in zebrafish."	( Protective effects of genistein and estradiol on PAHs-induced developmental toxicity in zebrafish embryos. Bai, C; Chen, J; Cui, Y; Huang, C; Lu, F; Ren, X; Wang, X; Yang, D, 2012)	0.38
"Because polycyclic aromatic hydrocarbons (PAHs) and polybrominated diphenylethers (PBDEs) are ubiquitous and coexist in the environment and in wildlife, there are potential interactions between them that could cause toxic effects."	( Modulation of benzo[a]pyrene-induced toxic effects in Japanese medaka (Oryzias latipes) by 2,2',4,4'-tetrabromodiphenyl ether. Fan, Z; Hu, J; Huang, C; Luo, K; Zhao, Y, 2013)	0.39
" Can reliable predictions of the aquatic toxicity of crude oil, a multi-component mixture, be described from toxicity data on individual PAH compounds? Naphthalene, the most abundant PAH compound, and benzo(a)pyrene, a highly toxic PAH compound, were selected as model compounds to quantify toxicity of crude oil on two phytoplankton species, Ditylum brightwellii and Heterocapsa triquetra, by analyzing the effects of different concentrations of these PAHs on growth rate."	( Can crude oil toxicity on phytoplankton be predicted based on toxicity data on benzo(a)pyrene and naphthalene? Bargu, S; Ozhan, K, 2014)	0.82
"5) collected at four localities from heavily polluted areas of the Czech Republic or two representative toxic polycyclic aromatic hydrocarbons (PAHs) present in EOMs, benzo[a]pyrene (B[a]P) and benzo[k]fluoranthene (B[k]F)."	( Genotoxicity but not the AhR-mediated activity of PAHs is inhibited by other components of complex mixtures of ambient air pollutants. Ciganek, M; Kléma, J; Krčková, S; Líbalová, H; Machala, M; Milcová, A; Schmuczerová, J; Šrám, RJ; Topinka, J; Uhlířová, K, 2014)	0.4
" In TD modeling, aryl hydrocarbon hydroxylase (AHH) activity assay, comet assay, protein carbonyl measurement and lipid peroxidation level determination in digestive gland were used as biomarkers to reflect toxic effects."	( A physiologically based toxicokinetic and toxicodynamic model links the tissue distribution of benzo[a]pyrene and toxic effects in the scallop Chlamys farreri. Liu, D; Pan, L; Wang, J; Yang, H, 2014)	0.4
" The objectives of the present study were to investigate the adverse effects of BaP on normal human lung epithelial cells (BEAS-2B), the potential protective effects of curcumin and VE against BaP-induced cellular damage, and the molecular mechanisms of action."	( Curcumin and vitamin E protect against adverse effects of benzo[a]pyrene in lung epithelial cells. Cai, Q; Cromie, MM; Gao, W; Lv, T; Singh, K; Zhu, W, 2014)	0.4
" The toxic effects of BaP on fish embryos have been described in detail, but some potentially toxic effects of BaP might have been neglected owing to the limitations of traditional techniques."	( Use of toxicogenomics to predict the potential toxic effect of Benzo(a)pyrene on zebrafish embryos: ocular developmental toxicity. Huang, L; Lin, JJ; Wang, C; Wu, M; Zhang, Y; Zuo, Z, 2014)	0.64
" The most toxic fraction contained several known aryl hydrocarbon receptor (AhR) agonists (e."	( Effect-directed analysis of Elizabeth River porewater: developmental toxicity in zebrafish (Danio rerio). Clark, BW; Cooper, EM; Di Giulio, RT; Fang, M; Ferguson, PL; Garner, LV; Getzinger, GJ; Stapleton, HM, 2014)	0.4
" In behavior test it showed that there was an adverse effect on rats in the B(a)P -group."	( Adverse effect of sub-chronic exposure to benzo(a)pyrene and protective effect of butylated hydroxyanisole on learning and memory ability in male Sprague-Dawley rat. Cao, X; Cheng, S; Duan, L; Liang, X; Luo, L; Tang, Y; Tu, B, 2014)	0.67
"A whole-cell bacterial bioreporter Acinetobacter baylyi strain ADP1_recA_lux that responds to genotoxins was employed to directly assess the adverse effects of the bioavailable fraction of mitomycin C (MMC), benzo[a]pyrene (BaP), chromium (VI) and lead (II) in amended soils and soil samples from two fragile areas in China without soil pre-treatment."	( A whole-cell bioreporter approach for the genotoxicity assessment of bioavailability of toxic compounds in contaminated soil in China. Huang, WE; Jia, J; Jiang, B; Li, C; Li, G; Liu, Z; Song, Y; Tang, H; Tian, S; Zhang, X, 2014)	0.4
"The purpose of this study was to investigate the toxic effects induced by benzo[a]pyrene (BaP)."	( Toxic effects upon exposure to benzo[a]pyrene in juvenile white shrimp Litopenaeus vannamei. Pan, L; Ren, X; Wang, L, 2015)	0.42
"The aryl hydrocarbon receptor (AHR) is a ligand-activated transcription factor that mediates many of the toxic effects of dioxin-like compounds (DLCs) and some polycyclic aromatic hydrocarbons (PAHs)."	( Zebrafish cardiotoxicity: the effects of CYP1A inhibition and AHR2 knockdown following exposure to weak aryl hydrocarbon receptor agonists. Brown, DR; Clark, BW; Di Giulio, RT; Garner, LV, 2015)	0.42
"Benzo[a]pyrene (BaP) is a priority Polycyclic Aromatic Hydrocarbon (PAH), which is toxic to aquatic organisms and has been widely detected in the environment."	( Comparison of species sensitivity distributions constructed with predicted acute toxicity data from interspecies correlation estimation models and measured acute data for benzo[a]pyrene. Gao, X; Lin, Y; Liu, Z; Ni, J; Shi, X; Wu, J; Yan, Z; Yi, X, 2016)	0.43
" However, little is known about the constituents of wood smoke and biological mechanisms that are responsible for adverse health effects."	( Toxicity of wood smoke particles in human A549 lung epithelial cells: the role of PAHs, soot and zinc. Diabaté, S; Dilger, M; Orasche, J; Paur, HR; Weiss, C; Zimmermann, R, 2016)	0.43
"Evaluation of DNA quality of gametes is a relevant method to predict potential consequences of pollutants in the next generations, as it allows to define adverse outcome pathways implicated in pollutant-mediated toxicity for risk assessment."	( Spermatozoa: A relevant biological target for genotoxicity assessment of contaminants in the estuarine bivalve Scrobicularia plana. Bruneau, M; Châtel, A; Goupil, A; Lièvre, C; Mouneyrac, C, 2017)	0.46
" The effect of ozonation was immediate in the BaP solution; 89% of this toxic compound was decomposed after only 1 min of treatment."	( Efficacy of Ozonation Treatments of Smoked Fish for Reducing Its Benzo[a]pyrene Concentration and Toxicity. Ancans, J; Bartkevics, V; Bartkiene, E; Rozentale, I; Viksna, A, 2016)	0.43
" In this study, we focused on the toxic effects of BaP (1 µg/L and 10 µg/L) on gills of the pearl oyster Pinctada martensii using combined metabolomic and proteomic approaches."	( An integrated metabolomic and proteomic study of toxic effects of Benzo[a]pyrene on gills of the pearl oyster Pinctada martensii. Chen, H; Diao, X; Wang, H; Zhou, H, 2018)	0.48
" The aim of this study was to investigate the mechanism by which folic acid can inhibit the toxic effects of BaP both in vivo and in vitro."	( The intervention mechanism of folic acid for benzo(a)pyrene toxic effects in vitro and in vivo. Chen, Y; Gong, Z; Wang, L; Wang, P; Wu, Y, 2019)	0.77
"Several studies have suggested that air pollutants combine exposure have greater adverse effects."	( Gene profiles to characterize the combined toxicity induced by low level co-exposure of silica nanoparticles and benzo[a]pyrene using whole genome microarrays in zebrafish embryos. Asweto, CO; Duan, J; Hu, H; Liang, S; Liu, M; Sun, Z; Wang, L; Yang, H, 2018)	0.48
"Benzo(a)pyrene (BaP) is a highly toxic polycyclic aromatic hydrocarbon and has strong affinity to suspended materials and sediments in the aquatic environment."	( Growth, energy metabolism and transcriptomic responses in Chinese mitten crab (Eriocheir sinensis) to benzo[α]pyrene (BaP) toxicity. Chen, L; Ding, Q; Li, E; Qin, JG; Wang, X; Yu, N, 2018)	1.92
" We compared the developmental neurotoxicity of nicotine to that of the PAH archetype, benzo[a]pyrene (BaP), and also evaluated the effects of combined exposure to assess whether PAHs might exacerbate the adverse effects of nicotine."	( The Developmental Neurotoxicity of Tobacco Smoke Can Be Mimicked by a Combination of Nicotine and Benzo[a]Pyrene: Effects on Cholinergic and Serotonergic Systems. Ko, A; Levin, ED; Seidler, FJ; Skavicus, S; Slotkin, TA, 2019)	0.51
"Skin is a major barrier against external insults and is exposed to combinations of chemical and/or physical toxic agents."	( Solar simulated light exposure alters metabolization and genotoxicity induced by benzo[a]pyrene in human skin. Béal, D; Bourgart, E; Calissi, C; Douki, T; Giot, JP; Leccia, MT; Maitre, A; Marques, M; von Koschembahr, A; Youssef, A, 2018)	0.48
"Cadmium (Cd) and benzo [a]pyrene (BaP) often co-occur in the environment, and the critical body residue of organisms is used as an indicator of the toxic effects of contaminants."	( Benzo(a)pyrene inhibits the accumulation and toxicity of cadmium in subcellular fractions of Eisenia fetida. Han, L; Hu, F; Li, H; Norton, JM; Xu, L; Zhang, L; Zhao, C; Zhou, L, 2019)	1.96
" In utero B[a]P exposure exerts multiple adverse effects on embryo development, although the underlying molecular mechanisms have still not been clearly elucidated."	( A human embryonic stem cell-based model for benzo[a]pyrene-induced embryotoxicity. Chi, Y; Dong, S; Wang, H; Zhu, Y, 2019)	0.51
"To examine the adverse effects of the benzo[α]pyrene (B[α]P), the monogonont rotifer Brachionus rotundiformis was exposed to various concentration of B[α]P (0 [control], 1, 10, and 100 μg/L) and measured life cycle parameters (e."	( Adverse effects, expression of defense-related genes, and oxidative stress-induced MAPK pathway in the benzo[α]pyrene-exposed rotifer Brachionus rotundiformis. Byeon, E; Han, J; Hwang, UK; Kang, HM; Lee, JS; Lee, MC; Park, JC; Sayed, AEH; Yoon, DS, 2019)	0.51
" Combined exposure to F-MWCNTs and BaP decreases cytotoxicity compared to individual exposure, but the difference is not statistically significant in all toxicity assays; hence, the two-factorial analysis indicated an additive toxic interaction."	( Individual and combined toxicity of carboxylic acid functionalized multi-walled carbon nanotubes and benzo a pyrene in lung adenocarcinoma cells. Khodagholi, F; Mehrabi, Y; Mohammadian, Y; Omidi, M; Peirovi, H; Pourahmad, J; Rafieepour, A; Rezazadeh Azari, M, 2019)	0.51
" Persistent organic compounds polychlorinated biphenyls (PCBs) could exert toxic effects on Zebrafish embryos through affecting amino acid metabolism, DNA and protein methylation and biosynthesis."	( [Progress in study on the role of metabolomics in toxic effects of environmental pollutants and the underlying mechanism]. Fu, J; Hu, J, 2019)	0.51
" In this study, we evaluated the toxic effects of intratracheally instilled benzo[a]pyrene (B[a]P) on hepatic lipid metabolism of C57BL/6 mice at relevant environmental exposure levels by using two different mass-based lipidomics approaches."	( Hepatotoxic effects of inhalation exposure to polycyclic aromatic hydrocarbons on lipid metabolism of C57BL/6 mice. Jin, Y; Li, C; Li, F; Li, J; Luo, Q; Ren, S; Wu, Y; Xiang, B, 2020)	0.56
"Polycyclic aromatic hydrocarbons (PAHs), such as benzo[a]pyrene (BaP), are widely distributed in air, water, and sediments; however, limited data are available regarding their potential adverse effects on the early life stages of fish."	( Potential mechanisms underlying embryonic developmental toxicity caused by benzo[a]pyrene in Japanese medaka (Oryzias latipes). Arizono, K; Hirano, M; Ichikawa, N; Ishibashi, H; Koyama, J; Tominaga, N; Uchida, M; Yamaguchi, A, 2020)	0.56
" Accordingly, both adverse effects were diminished with a lower concentration of B[a]P and a lower SSL dose, leading to less oxidative stress."	( Toxicity and DNA repair in normal human keratinocytes co-exposed to benzo[a]pyrene and sunlight. Béal, D; Douki, T; Giot, JP; Gudimard, L; von Koschembahr, A; Youssef, A, 2020)	0.56
"Increasing production of corannulene (COR), a non-planar polycyclic aromatic hydrocarbon (PAH) with promising applications in many fields, has raised a concern about its potential toxic effects."	( Comparative toxicity analysis of corannulene and benzo[a]pyrene in mice. Bi, Y; Huang, J; Li, C; Li, G; Ma, R; Saeed, K; Xing, Y; Xiong, H; Zhang, Y, 2020)	0.56
"Benzo[a]pyrene (BaP), a widely existed polycyclic aromatic hydrocarbon pollutant in aquatic environment, has toxic effects on marine animals and their generations, but the intergenerational immunotoxic mechanism underlying has not been clearly understood."	( The intergenerational toxic effects on offspring of medaka fish Oryzias melastigma from parental benzo[a]pyrene exposure via interference of the circadian rhythm. Chen, F; Chen, H; Liu, Y; Wang, KJ; Yin, X; Zeb, R, 2020)	0.56
"The aim: of this work was to experimentally study the modifying role of toxic substances (phenol) in the manifestation of genotoxic and immunological changes in the body when exposed to a carcinogen (benzo[a]pyrene)."	( THE MODIFYING ROLE OF TOXIC SUBSTANCES ON GENOTOXIC EFFECT IN THE BODY DURING COMBINED ADMINISTRATION WITH CARCINOGEN (BENZO[A]PYRENE). Balenko, NV; Chernychenko, IO; Grygorenko, LE; Ostash, OM; Shvager, OV; Stepanchuk, SV, 2021)	0.62
"In natural environment, the existence of interactions of toxic mixtures could induce diverse biochemical pathways and consequently exert different toxicological responses in aquatic organisms."	( The cadmium toxicity in gills of Mytilus coruscus was accentuated by benzo(a)pyrene of higher dose but not lower dose. Li, P; Wang, H; Xu, K, 2021)	0.86
" The most notable tissue-specific effects and morphometric endpoints were observed upon sub-chronic exposure, such as changes in key genes involved in detoxification, DNA damage, and altered reproductive morphological endpoints; showing that sub-chronic BaP doses have longer-lasting toxic effects."	( Gene expression analysis on growth, development and toxicity pathways of male Nile tilapia (Oreochromis niloticus), after acute and sub-chronic benzo (α) pyrene exposures. Albores-Medina, A; Albornoz-Abud, NA; Cañizares-Martínez, MA; Canul-Marín, GF; Chan-Cuá, I; Colli-Dula, RC; Hernández-Núñez, E; Rodríguez-Canul, R; Valdés-Lozano, D, 2021)	0.62
" Beside some well-documented adverse effects on the development and reproduction of aquatic organisms, BaP was recently shown to affect fish bone formation and skeletal development through mechanisms that remain poorly understood."	( New insights into benzo[⍺]pyrene osteotoxicity in zebrafish. Bebianno, MJ; Bensimon-Brito, A; Cancela, ML; Cardeira-da-Silva, J; Cordelières, FP; Gavaia, PJ; Günther, S; Laizé, V; Ramkumar, S; Stainier, DYR; Tarasco, M, 2021)	0.62
"The quantitative adverse outcome pathway (qAOP) is proposed to inform dose-responses at multiple biological levels for the purpose of toxicity prediction."	( High throughput data-based, toxicity pathway-oriented development of a quantitative adverse outcome pathway network linking AHR activation to lung damages. Chen, N; Chen, S; Guan, H; Jin, Y; Li, C; Li, D; Liu, Y; Luo, J; Ma, W; Qi, G; Shou, Y; Xu, L; Yu, D; Zhang, Q; Zheng, Y, 2022)	0.72
"04 μg/L B[a]P could play the adverse role in DNA integrity at the mature and spawn stages."	( Reproductive toxicity induced by benzo[a]pyrene exposure: first exploration highlighting the multi-stage molecular mechanism in female scallop Chlamys farreri. Gao, Z; Li, D; Miao, J; Pan, L; Xu, R; Yang, Y; Zhou, Y, 2022)	0.72
" Data demonstrated that flame retarded furnishings slowed the generation of toxic levels of acutely toxic gases."	( Evaluation of potential toxicity of smoke from controlled burns of furnished rooms - effect of flame retardancy. Blais, MS; Droege, W; Hendriks, G; Osimitz, TG, 2022)	0.72
" In the current study, the combined toxic effects of B[a] P and Cr(VI) were studied in human bronchial epithelial cells (16 HBE)."	( Effects of chromium (VI) on the toxicity of benzo[z]pyrene in 16HBE cells. Wang, J; Xia, B, 2022)	0.72
" Here, a new "Bottom-up" approach was proposed to identify miRNAs that are responsible for environmental exposure-induced adverse outcomes."	( Identifying microRNAs that drive BaP-induced pulmonary effects: Multiple patterns of mechanisms underlying activation of the toxicity pathways. Chen, N; Du, C; Guan, H; Jin, Y; Li, C; Liu, Y; Luo, J; Ma, W; Shou, Y; Xu, L; Yu, D; Zhang, Q; Zhao, K; Zheng, Y, 2022)	0.72
" Single exposure of PS MPs or B[a]P decreased the mean epithelial thickness (MET) of digestive tubules and enhanced reactive oxygen species (ROS) levels in haemolymph, while upon co-exposure the adverse impacts were alleviated."	( Polystyrene microplastics alleviate adverse effects of benzo[a]pyrene on tissues and cells of the marine mussel, Mytilus galloprovincialis. Cong, Y; Ding, G; Li, Z; Shi, H; Wang, J; Wang, Y; Zhang, M, 2023)	0.91
" Combined with the effects of environmental concentrations, the toxic effects of low concentrations of commercially available NAs (0."	( Transcriptome reveals the toxicity and genetic response of zebrafish to naphthenic acids and benzo[a]pyrene at ambient concentrations. Kong, Q; Ma, J; Si, P; Zhang, H, 2023)	0.91
" Indeed, in some of the multi-dose animal studies, maximal adverse effects were observed at lower B[a]P doses, according to a non-monotonic dose-response curve typical of endocrine-disrupting compounds."	( Developmental exposure to polycyclic aromatic hydrocarbons (PAHs): Focus on benzo[a]pyrene neurotoxicity. Racca, A; Ricceri, L; Tartaglione, AM, 2023)	0.91

Excerpt	Reference	Relevance
" We have described the metabolic elimination of B(a)P using a physiologically based pharmacokinetic model applied retrospectively to existing data sets of B(a)P metabolism and disposition in rats."	( Action by the lungs on circulating xenobiotic agents, with a case study of physiologically based pharmacokinetic modeling of benzo(a)pyrene disposition. Roth, RA; Vinegar, A, 1990)	0.49
" BaP entered the blood rapidly with an average half-life of 11 min in experiments in which the IPLs received only BaP on perfusion."	( The pharmacokinetics of benzo[alpha]pyrene in the isolated perfused rabbit lung: the influence of benzo[alpha]pyrene, n-dodecane, particulate, or sulfur dioxide. Bingham, E; Morgan, DD; Niemeier, RW; Warshawsky, D, 1984)	0.27
" Despite significant public health concern, physiologically based pharmacokinetic (PBPK) modeling efforts for PAHs have so far been limited to naphthalene, plus simpler PK models for pyrene, nitropyrene, and benzo[a]pyrene (B[a]P)."	( Preliminary physiologically based pharmacokinetic models for benzo[a]pyrene and dibenzo[def,p]chrysene in rodents. Amin, SG; Anderson, KA; Corley, RA; Crowell, SR; Krishnegowda, G; Sharma, AK; Soelberg, JJ; Williams, DE, 2011)	0.37
" A rat physiologically-based pharmacokinetic model of BaP and 3-OHBaP was built."	( Understanding the linked kinetics of benzo(a)pyrene and 3-hydroxybenzo(a)pyrene biomarker of exposure using physiologically-based pharmacokinetic modelling in rats. Bouchard, M; Heredia-Ortiz, R, 2013)	0.66
" In the present study, we have used a human physiologically-based pharmacokinetic (PBPK) model and an simple compartmental toxicokinetic model of benzo(a)pyrene (BaP) kinetics and its 3-hydroxybenzo(a)pyrene (3-OHBaP) metabolite to reproduce the time-course of this biomarker of exposure in the urine of industrially exposed workers and in turn predict the most plausible exposure scenarios."	( Use of physiologically-based pharmacokinetic modeling to simulate the profiles of 3-hydroxybenzo(a)pyrene in workers exposed to polycyclic aromatic hydrocarbons. Barbeau, D; Bouchard, M; Heredia Ortiz, R; Lafontaine, M; Maître, A, 2014)	0.82
" A physiologically based pharmacokinetic (PBPK) model for BaP for the rat was extended to simulate inhalation exposures to BaP in rats and humans including particle deposition and dissolution of absorbed BaP and renal elimination of 3-hydroxy benzo[a]pyrene (3-OH BaP) in humans."	( Predicting lung dosimetry of inhaled particleborne benzo[a]pyrene using physiologically based pharmacokinetic modeling. Campbell, J; Clewell, H; Crowell, S; Franzen, A; Gentry, R; Loccisano, A; Lumpkin, M; Meredith, C; Van Landingham, C, 2016)	0.43
" The time courses of BaP and 3-OHBaP were simulated by using a physiologically based pharmacokinetic model with Advanced Continuous Simulation Language (ACSLX)."	( Physiologically-based pharmacokinetic modeling of benzo(a)pyrene and the metabolite in humans of different ages. Deng, L; Deng, Q; Liu, H, 2021)	0.87

Excerpt	Reference	Relevance
" These data demonstrate that sequential treatment with BaP in combination with MeoA is associated with induction of highly proliferative phenotypes in GMCs characterized by differential expression of growth-related protooncogenes."	( Induction of highly proliferative phenotypes in cultured glomerular mesangial cells by benzo[a]pyrene alone or in combination with methoxamine. Bowes, RC; Ramos, KS; Weber, TJ, 1995)	0.29
" Resveratrol partially reversed the inhibitory effects of low concentrations of LPS alone, and completely reversed the inhibition of nodule formation when low concentrations of LPS were combined with BaP."	( Inhibition of osteogenesis in vitro by a cigarette smoke-associated hydrocarbon combined with Porphyromonas gingivalis lipopolysaccharide: reversal by resveratrol. Andreou, V; Casper, RF; D'Addario, M; Ellen, RP; Sukhu, B; Tenenbaum, HC; Zohar, R, 2004)	0.32
" Melatonin in combination with B(a)P induced rises in the GSH level in liver and brain, as compared to the receiving B(a)P alone."	( Effects of melatonin on lipid peroxidation and antioxidative enzyme activities in the liver, kidneys and brain of rats administered with benzo(a)pyrene. Dzięgiel, P; Januszewska, L; Jethon, Z; Magdalan, J; Murawska-Ciałowicz, E; Podhorska-Okołów, M; Sozański, T; Zawadzki, M, 2011)	0.57
" Thus, we investigated whether quercetin supplementation suppresses the harmful effects of benzo[a]pyrene (BaP) alone or combined with β-carotene in the lungs of Mongolian gerbils."	( Quercetin supplementation suppresses the secretion of pro-inflammatory cytokines in the lungs of Mongolian gerbils and in A549 cells exposed to benzo[a]pyrene alone or in combination with β-carotene: in vivo and ex vivo studies. Chan, ST; Chuang, CH; Liao, JW; Liu, KL; Tseng, MJ; Yeh, CL; Yeh, SL, 2012)	0.38

Excerpt	Reference	Relevance
" Oral bioavailability of a mixture of naturally produced metabolites was significantly less than that of the parent BaP."	( Relative bioavailability and DNA adduct formation of benzo[a]pyrene and metabolites in the diet of the winter flounder. Cahill, JM; Kleinow, KM; McElroy, AE; Sisson, JD, 1991)	0.28
"To evaluate health risks associated with exposure to particulates in the environment, it is necessary to quantify the bioavailability of carcinogens associated with the particulates."	( Bioavailability in vivo of benzo[a]pyrene adsorbed to diesel particulate. Bevan, DR; Ruggio, DM, 1991)	0.28
"The role of absorption rate and enzyme activity on cutaneous metabolism of topically applied xenobiotics was assessed by determining the simultaneous percutaneous penetration/metabolism of benzo[a]pyrene (B[a]P) and 7-ethoxycoumarin (7-EC) in intact, metabolically viable skin of Sencar mice, hairless guinea pigs, and humans."	( Metabolism of xenobiotics during percutaneous penetration: role of absorption rate and cutaneous enzyme activity. Bronaugh, RL; Collier, SW; Stewart, RF; Storm, JE, 1990)	0.28
"Little is known about the bioavailability of inhaled organic compounds that are associated with particles."	( Studies on the ability of rat lung and liver microsomes to facilitate transfer and metabolism of benzo[a]pyrene from diesel particles. Bond, JA; Henderson, RF; Leung, HW; Mauderly, JL; McClellan, RO, 1988)	0.27
" In all four samples, an increase in humus concentration decreased the bioavailability of BaP in a logarithmic manner."	( Effects of humus concentrations on benzo[a]pyrene accumulation from water to Daphnia magna: comparison of natural waters and standard preparations. Gjessing, E; Johnsen, S; Kukkonen, J; Oikari, A, 1989)	0.28
" Calculations of bioavailability and mean dissolution time in the lung produced results in concordance with experimental data."	( Bioavailability of benzo(a)pyrene deposited in the lung. Correlation with dissolution from urban air particulates and covalently bound DNA adducts. Nicklasson, M; Nybom, L; Söderkvist, P; Toftgård, R; Törnquist, S, )	0.46
" These highly lipophilic compounds are well absorbed in the intestine."	( The influence of bile on the bioavailability of polynuclear aromatic hydrocarbons from the rat intestine. Barrowman, JA; Rahimtula, A; Rahman, A, 1986)	0.27
" The bioavailability was determined to be about 10% in these experiments."	( Pharmacokinetics of low doses of benzo[a]pyrene in the rat. Foth, H; Kahl, GF; Kahl, R, 1988)	0.27
" However, methods developed in these experiments will facilitate future studies of the bioavailability of endogenous BaP on carbon blacks, especially in terms of determining the experimental conditions under which elution may occur."	( Elution of benzo[a]pyrene from carbon blacks into biomembranes in vitro. Bevan, DR; Worrell, WJ, 1985)	0.27
" This technique provides a convenient method for evaluating the potential bioavailability of PAH associated with other carbonaceous particulates which occur in the environment."	( In vitro technique to study elution of benzo[a]pyrene from particulates into biomembranes with application to woodstove particulates. Bevan, DR; Yonda, NT, 1985)	0.27
" The toxicology of dihydrodiol is more complex than what can be deduced solely on the basis of diminished bioavailability of the epoxide precursor, and the increased hydrophilicity associated with the dihydrodiol moiety."	( Toxicological significance of dihydrodiol metabolites. Hsia, MT, 1982)	0.26
"This study assessed the effect of concomitant lipid absorption on the bioavailability and lymphatic transport of benzo(a)pyrene (BP), a carcinogenic polycyclic aromatic hydrocarbon (PAH)."	( Similar bioavailability and lymphatic transport of benzo(a)pyrene when administered to rats in different amounts of dietary fat. Barrowman, JA; Laher, JM; Patton, JS; Rigler, MW; Vetter, RD, 1984)	0.73
" In summary, the in vitro data was consistent with the in vivo data in demonstrating that 14C-benzo[a]pyrene was well absorbed through skin."	( In vivo and in vitro dermal absorption of benzo[a]pyrene in rat, guinea pig, human and tissue-cultured skin. Chu, I; Moody, RP; Nadeau, B, 1995)	0.29
"In isopods from contaminated sites relatively low levels of high molecular weight polycyclic aromatic hydrocarbons (PAHs) have been observed, which may be caused by either a low bioavailability or a high elimination rate."	( Uptake and elimination of benzo[a]pyrene in the terrestrial isopod Porcellio scaber. van Brummelen, TC; van Straalen, NM, 1996)	0.29
" This study examined the effect of dose and previous dietary exposure to the inducer ss-naphthoflavone (BNF) upon the intestinal metabolism of BaP and the systemic bioavailability of BaP-derived products in catfish."	( Bioavailability and biotransformation of benzo(a)pyrene in an isolated perfused In situ catfish intestinal preparation. James, MO; Kleinow, KM; Tong, Z; Venugopalan, CS, 1998)	0.57
" Bioavailability of sediment-sorbed PAHs declined with contact time between sediment and animals."	( Accumulation kinetics of polycyclic aromatic hydrocarbons adsorbed to sediment by the mollusk Corbicula fluminea. Djomo, JE; Ferrier, V; Garrigues, P; Narbonne, JF; Ribera, D, 1999)	0.3
" Systemic bioavailability (body uptake) is viewed as a good indicator of skin penetration following cutaneous exposures."	( Studies on the dermal and systemic bioavailability of polycyclic aromatic compounds in high viscosity oil products. Booth, ED; Brandt, HC; Loose, RW; Potter, D; Priston, RA; Watson, WP; Wright, AS, )	0.13
" The degree of adduct formation from a particular oil product, which we term the Bioavailability Index (BI), was shown to be a function of both the viscosity of the oil product, which affected the transport of the PAC through the carrier, and the aromaticity, which affected the partition of PAC between the carrier and the skin."	( Development of a carcinogenic potency index for dermal exposure to viscous oil products. Booth, ED; Brandt, HC; de Groot, PC; Watson, WP, )	0.13
" The difference in octanol-water partition coefficient, log P(ow) between n-dodecane compared to tetrahydrofuran is considered to be the most likely reason for the reduction in the bioavailability of benzo(a)pyrene and/or its metabolites and hence the degree of genotoxicity in tissues."	( Effects of solvent on DNA adduct formation in skin and lung of CD1 mice exposed cutaneously to benzo(a)pyrene. Booth, ED; Loose, RW; Watson, WP, 1999)	0.71
" Time-course bioavailability results indicated that greater than 95% of the parent compound is cleared from blood 240 min postexposure."	( Modulation in the developmental expression profile of Sp1 subsequent to transplacental exposure of fetal rats to desorbed benzo[a]pyrene following maternal inhalation. Greenwood, M; Hood, DB; Inyang, F; Nayyar, T; Ramesh, A, 2000)	0.31
" 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
", ozonation and biodegradation) to overcome the inherent bacterial bioavailability limitation, and hence bioremediation limitation, of polycyclic aromatic hydrocarbons in soil."	( Combined ozonation and biodegradation for remediation of mixtures of polycyclic aromatic hydrocarbons in soil. Kukor, JJ; Nam, K, 2000)	0.31
" The results suggest that chemically dispersing oil may have the greatest effect on bioavailability of hydrocarbons, both through waterborne and food chain exposures."	( The effect of different oil spill remediation techniques on petroleum hydrocarbon elimination in Australian bass (Macquaria novemaculeata). Cohen, AM; Gagnon, MM; Nugegoda, D, 2001)	0.31
" The bioavailability of BaP increased as a function of exposure concentration, and toxicokinetic analysis indicates first-order pharmacokinetics for BaP."	( Toxicokinetics of inhaled benzo[a]pyrene: plasma and lung bioavailability. Greenwood, M; Hood, DB; Inyang, F; Ramesh, A, 2001)	0.31
"Contaminant bioavailability via digestive exposure was examined for 18 species of marine benthic invertebrates, using incubation of digestive fluids with sediments that were spiked with either radiolabeled benzo-[a]-pyrene (BaP) or zinc."	( Benzo[a]pyrene and zinc solubilization by digestive fluids of benthic invertebrates--a cross-phyletic study. Bock, MJ; Mayer, LM; Weston, DP, 2001)	0.31
" The extractability of BaP and HCBP from sediment using traditional solvents was then compared to the transfer efficiency (TE) of a benthic invertebrate (Lumbriculus variegatus) to relate chemical extractability to bioavailability in the organisms."	( Chemical and biological availability of sediment-sorbed benzo[a]pyrene and hexachlorobiphenyl. Lydy, MJ; Schuler, LJ, 2001)	0.31
" Recent studies in mammals suggest that intestinal pgp may modulate intestinal bioavailability of dietary xenobiotics."	( P-glycoprotein in the catfish intestine: inducibility by xenobiotics and functional properties. Doi, AM; Holmes, E; Kleinow, KM, 2001)	0.31
"The objective of this study was to evaluate the bioavailability of Benzo(a)pyrene [B(a)p], subsequent to oral exposure."	( Metabolism, bioavailability, and toxicokinetics of benzo(alpha)pyrene in F-344 rats following oral administration. Archibong, AE; Hood, DB; Inyang, F; Knuckles, ME; Nyanda, AM; Ramesh, A, 2001)	0.55
" The effects of dissolved organic matter (DOM) on the bioavailability of atrazine, pyrene and benzo[a]pyrene (B[a]P) was evaluated."	( Bioavailability of atrazine, pyrene and benzo[a]pyrene in European river waters. Akkanen, J; Haitzer, M; Kukkonen, JV; Penttinen, S, 2001)	0.31
"A series of experiments were conducted with benzo(a)pyrene (B(a)P) spiked sediments to determine if bioavailability of sediment-associated contaminants is affected by multiple species interactions."	( Bioavailability of sediment-associated benzo(a)pyrene within single- versus multiple-species systems. Heagler, MG; Lydy, MJ; Schuler, LJ, 2002)	0.85
" 14C portal absorption rate was high for 14C-phenanthrene (95%), it was close to 33% for 14C-benzo[a]pyrene and very low for 14C-TCDD (9%)."	( Portal absorption of 14C after ingestion of spiked milk with 14C-phenanthrene, 14C-benzo[a]pyrene or 14C-TCDD in growing pigs. Feidt, C; Grova, N; Laurent, C; Laurent, F; Lichtfouse, E; Mpassi, D; Rychen, G, 2002)	0.31
" These results suggest that strain BPC1 has a specialized niche in the benzo[a]pyrene-mineralizing consortium; namely, it grows on metabolites produced by fellow members and contributes to benzo[a]pyrene mineralization by increasing the bioavailability of this compound."	( Rhodanobacter sp. strain BPC1 in a benzo[a]pyrene-mineralizing bacterial consortium. Harayama, S; Kanaly, RA; Watanabe, K, 2002)	0.31
" Multiple molecular biomarkers provided a sensitive, physiologically based method of determining contaminant presence and bioavailability to aquatic organisms."	( Laboratory and field validation of multiple molecular biomarkers of contaminant exposure in rainbow trout (Oncorhynchus mykiss). Burton, GA; Lattier, D; McClain, JS; Oris, JT, 2003)	0.32
" Overall, the bioavailability of HCBP in spiked sediments tended to decrease with duration of aging, based on k(s) values and bioaccumulation factors (BAFs)."	( Toxicokinetics of sediment-sorbed benzo[a]pyrene and hexachlorobiphenyl using the freshwater invertebrates Hyalella azteca, Chironomus tentans, and Lumbriculus variegatus. Bailer, AJ; Lydy, MJ; Schuler, LJ; Wheeler, M, 2003)	0.32
" Results showed that bioavailability of the model compounds was reduced by the presence of DOM."	( Measuring the bioavailability of two hydrophobic organic compounds in the presence of dissolved organic matter. Akkanen, J; Kukkonen, JV, 2003)	0.32
" These findings suggest that the physicochemical properties of the xenobiotics and intestinal epithelium play key roles in the selective permeability and in the bioavailability of the tested micropollutants."	( Intestinal absorption of 14C from 14C-phenanthrene, 14C-benzo[a]pyrene and 14C-tetrachlorodibenzo-para-dioxin: approaches with the Caco-2 cell line and with portal absorption measurements in growing pigs. Cavret, S; Feidt, C; Laurent, C; Laurent, F; Rychen, G, )	0.13
"A study was conducted to determine the effect of nonaqueous-phase liquids (NAPLs) on the bioavailability of benzo[a]pyrene (BaP) in soil."	( Effect of nonaqueous-phase liquids on the availability of polycyclic aromatic hydrocarbons in soil for worm uptake and bacterial genotoxicity. Alexander, M; Alexander, RR; Quiñones-Rivera, A, 2003)	0.32
" Bioavailability of BaP in desorbed sediments was assessed by toxicokinetic measures of uptake, bioaccumulation, and elimination in the deposit-feeding, freshwater tubificid oligochaete Ilyodrilus templetoni."	( Bioavailability and assimilation of sediment-associated benzo[a]pyrene by Ilyodrilus templetoni (Oligochaeta). Fleeger, JW; Lu, X; Reible, DD, 2004)	0.32
" These results appear to be correlated with in vivo data on the effects of orally administered B[a]P, that is, low (10%) bioavailability in the rats and almost no acute lethal toxicity in rats or mice."	( Feasibility of a simple double-layered coculture system incorporating metabolic processes of the intestine and liver tissue: application to the analysis of benzo[a]pyrene toxicity. Choi, S; Nishikawa, M; Sakai, Y; Sakoda, A, 2004)	0.32
" Consequently, other factors, such as bioavailability of waterborne polycyclic aromatic hydrocarbons (PAHs) to the target cells, are important for the localization of PAH adducts in the gill."	( Cell-specific CYP1A expression and benzo[a]pyrene adduct formation in gills of rainbow trout (Oncorhynchus mykiss) following CYP1A induction in the laboratory and in the field. Brandt, I; Brunström, B; Ingebrigtsen, K; Jönsson, ME, 2004)	0.32
"We investigated the bioavailability via diet of spiked benzo[a]pyrene (BaP) and 2,2',5,5'-tetrachlorobiphenyl (PCB-52) from different carbonaceous (non-carbonate, carbon containing) particle types to clams (Macoma balthica) collected from San Francisco Bay."	( Effects of particulate carbonaceous matter on the bioavailability of benzo[a]pyrene and 2,2',5,5'-tetrachlorobiphenyl to the clam, Macoma balthica. Allen-King, RM; Luoma, SN; Luthy, RG; McLeod, PB; van den Heuvel-Greve, MJ, 2004)	0.32
" A "relative risk index" (RRI) was developed to account for the combined effects of compound-specific bioavailability and toxic potency in estimating excess cancer risk."	( Combined effects of contaminant desorption and toxicity on risk from PAH contaminated sediments. Kosson, DS; Rockne, KJ; Shor, LM; Taghon, GL; Young, LY, 2004)	0.32
"The influence of anaerobic conditions on aqueous-phase polycyclic aromatic hydrocarbon (PAH) bioavailability was investigated in laboratory microcosms."	( Impact of imposed anaerobic conditions and microbial activity on aqueous-phase solubility of polycyclic aromatic hydrocarbons from soil. Christman, RF; Pfaender, FK; Pravecek, TL, 2005)	0.33
" These findings suggested that intestinal metabolism might play a key role in intestinal barrier permeability and thus in the bioavailability of tested micropollutants."	( Intestinal metabolism of PAH: in vitro demonstration and study of its impact on PAH transfer through the intestinal epithelium. Cavret, S; Feidt, C, 2005)	0.33
"The biodegradation of two substrates and the ability of dissolved organic matter (DOM) to influence benzo[a]pyrene bioavailability as DOM biodegradation progressed were monitored in reactors."	( The ability of dissolved organic matter (DOM) to influence benzo[a]pyrene bioavailability increases with DOM biodegradation. Garric, J; Gourlay, C; Mouchel, JM; Tusseau-Vuillemin, MH, 2005)	0.33
"In bioavailability studies, the biota sediment accumulation factor (BSAF) is invoked to describe the thermodynamic partitioning of a hydrophobic organic contaminant (HOC) between the organism lipid and the organic carbon fraction of the sedimentary matrix and accounts for differences in bioavailability among sediments."	( The contrasting roles of sedimentary plant-derived carbon and black carbon on sediment-spiked hydrophobic organic contaminant bioavailability to Diporeia species and Lumbriculus variegatus. Gossiaux, DC; Gunnarsson, J; Kukkonen, JV; Landrum, PF; Mitra, S; Weston, D, 2005)	0.33
"Biotransformation in the intestine may influence the bioavailability and toxicity of ingested xenobiotics."	( Properties and regional expression of a CYP3A-like protein in channel catfish intestine. Celander, MC; James, MO; Lou, Z; Rowland-Faux, L, 2005)	0.33
"In order to better asses the influence of organic matter on the bioavailability of hydrophobic organic contaminants, the effect of algae and POM of bacterial origin on the bioaccumulation of benzo[a]pyrene in Daphnia magna was evaluated."	( Influence of algal and bacterial particulate organic matter on benzo[a]pyrene bioaccumulation in Daphnia magna. Garric, J; Gourlay, C; Mouchel, JM; Tusseau-Vuillemin, MH, 2005)	0.33
" Production of mucus by the gills likely served to prevent lesions by reducing the bioavailability of the chemicals tested, which could explain that dose-effect relationships and synergistic effects were not observed."	( DNA damage (comet assay) and 8-oxodGuo (HPLC-EC) in relation to oxidative stress in the freshwater bivalve Unio tumidus. Charissou, AM; Cossu-Leguille, C; Lemiere, S; Vasseur, P, )	0.13
" Concerns exist regarding the long-term stability of sequestered contaminants in the environment, and stability needs to be demonstrated if bioavailability considerations are to be adopted into the risk assessment and remediation of contaminated land."	( Effect of cyclodextrin and transformer oil amendments on the chemical extractability of aged [14C]polychlorinated biphenyl and [14C]polycyclic aromatic hydrocarbon residues in soil. Burauel, P; Doick, KJ; Jones, KC; Semple, KT, 2005)	0.33
" The observed low bioavailability of PAHs probably inhibited PAH phytoremediation, as diffusion-limited mass transfer would limit the release of PAHs to the aqueous phase."	( Physicochemical characterization of coke-plant soil for the assessment of polycyclic aromatic hydrocarbon availability and the feasibility of phytoremediation. Ahn, S; Luthy, RG; Werner, D, 2005)	0.33
" At higher exposure levels the capacity of the epithelium to dissolve and metabolize BaP became saturated, and the absorption rate remained constant until crystalline BaP had dissolved, and the process proceeded with much smaller fractions of BaP metabolites produced in the mucosa."	( Increasing exposure levels cause an abrupt change in the absorption and metabolism of acutely inhaled benzo(a)pyrene in the isolated, ventilated, and perfused lung of the rat. Blomgren, B; Ewing, P; Gerde, P; Ryrfeldt, A, 2006)	0.55
"The high molecular weight polycyclic aromatic hydrocarbon (HMW PAH) benzo[a]pyrene is generally persistent in the environment and its persistence may be due to bioavailability limitations."	( Bioavailability of benzo[a]pyrene during NAPL-enhanced biodegradation in soil and in liquid culture. Kanaly, RA; Matsui, S; Watanabe, K, 2006)	0.33
" Hence, SFS is a potential means to simplify the present non-exhaustive hydroxypropyl-beta-cyclodextrin (HPCD)-based extraction technique for the evaluation of PAH bioavailability in soil."	( Rapid quantification of polycyclic aromatic hydrocarbons in hydroxypropyl-beta-cyclodextrin (HPCD) soil extracts by synchronous fluorescence spectroscopy (SFS). Broderick, J; Hua, G; Killham, K; Semple, KT; Singleton, I, 2007)	0.34
" The purpose of this research was to measure the bioavailability of [14C]-BaP bound to pristine soils or field-contaminated sediment using an in vitro model of gastrointestinal digestion followed by sorption to human enterocytes (Caco-2 cells) or to a surrogate membrane, ethylene vinyl acetate (EVA) thin film."	( Benzo[a]pyrene bioavailability from pristine soil and contaminated sediment assessed using two in vitro models. Eickhoff, C; Gobas, FA; Moore, MM; Pinto, LJ; Tsang, WS; Vasiluk, L; Walji, ZA, 2007)	0.34
" Soil parameters such as organic carbon content, structure and particle size distribution can modulate the bioavailability of contaminants to biological receptors."	( Hepatic and immune biological effect assays in C57BL/6 mice to measure polycyclic aromatic hydrocarbon bioavailability under laboratory exposures with increasing environmental relevance. Ataria, JM; Gooneratne, R; O'Halloran, K, 2007)	0.34
"In order to develop a new method to study the desorption and bioavailability of hydrophobic organic chemicals (HOCs) in soils, a method using semi-permeable membrane device (SPMD) to study desorption of HOCs in soils has been set up, and assisted desorption of polycyclic aromatic hydrocarbons (PAHs), phenanthrene(PHE), pyrene(PYE), and benzo[a] pyrene (B[a]PYE) in three different kinds of soils was studied using SPMD."	( [Desorption of polycyclic aromatic hydrocarbons in soils assisted by SPMD]. Huo, C; Sun, HW; Wang, CP, 2007)	0.34
" The bioavailability of BaP is discussed in relation to previous in vitro and in vivo studies in perspective with dermal exposure to contaminated soils."	( Contaminated soils (I): In vitro dermal absorption of benzo[a]pyrene in human skin. Chu, I; Joncas, J; Moody, RP; Richardson, M, 2007)	0.34
" It was concluded that adsorption of PAH onto these particles could decrease their bioavailability and so their abilities to affect cell cytokine production."	( Effect of polycyclic aromatic hydrocarbons and carbon black particles on pro-inflammatory cytokine secretion: impact of PAH coating onto particles. Bennasroune, A; Falla, J; Foucaud, L; Goulaouic, S; Laval-Gilly, P, 2008)	0.35
" Thus, temperature and aging had a minor effect on bioavailability estimates."	( Examining the role of temperature and sediment-chemical contact time on desorption and bioavailability of sediment-associated tetrabromo diphenyl ether and benzo(a)pyrene. Kukkonen, JV; Leppänen, MT; Sormunen, AJ, 2009)	0.55
" Results suggest the technique is not able to directly reflect bioavailability of BaP transformation products."	( Potential use of DNA adducts to detect mutagenic compounds in soil. Hua, G; Killham, K; Lyons, B; Singleton, I, 2009)	0.35
"Benzo[a]pyrene (B[a]P) conjugate vaccines based on ovalbumin, tetanus toxoid and diphtheria toxoid (DT) as carrier proteins were developed to investigate the effect of specific antibodies on the bioavailability of this ubiquitous carcinogen and its metabolites."	( Modulation of carcinogen bioavailability by immunisation with benzo[a]pyrene-conjugate vaccines. Farinelle, S; Grova, N; Muller, CP; Prodhomme, EJ; Schellenberger, MT, 2009)	0.35
" Thus, small-intestinal P450-mediated first-pass metabolism is a key determinant of the systemic bioavailability of oral BaP."	( The role of small-intestinal P450 enzymes in protection against systemic exposure of orally administered benzo[a]pyrene. Fang, C; Zhang, QY, 2010)	0.36
" Our data reveal that luteolin is able to interfere with crucial steps of drug metabolism and thereby enhances the bioavailability of B(a)P."	( Luteolin enhances the bioavailability of benzo(a)pyrene in human colon carcinoma cells. Abel, J; Bothe, H; Fritsche, E; Götz, C; Haarmann-Stemmann, T; Stobbe-Maicherski, N, 2010)	0.63
" Surfactants, known pharmaceutically to alter membrane permeability, change drug bioavailability and attenuate transporter function are also found in contaminant mixtures in the aquatic environment."	( Enhanced bioaccumulation of dietary contaminants in catfish with exposure to the waterborne surfactant linear alkylbenzene sulfonate. Kleinow, KM; Tan, X; Uppu, P; Yim, SY, 2010)	0.36
"Black carbon (BC) and chemical properties may play a significant role in defining the bioavailability of hydrophobic organic compounds (HOCs) in sediment."	( Influence of black carbon and chemical planarity on bioavailability of sediment-associated contaminants. Akkanen, J; Kukkonen, JV; Lydy, MJ; Pehkonen, S; You, J, 2010)	0.36
" A concordance between BaP reactive metabolite levels and adduct concentrations indicates that the bioavailability of reactive metabolites determines the binding with DNA and consequently the formation and persistence of adducts in an acute exposure regimen."	( Ovarian susceptibility to benzo[a]pyrene: tissue burden of metabolites and DNA adducts in F-344 rats. Archibong, AE; Niaz, MS; Ramesh, A, 2010)	0.36
" However, in this work, we demonstrate, for the first time, that, upon complexation of polyaromatic hydrocarbons with mucins, enhanced bioavailability and, therefore, toxicity are obtained."	( Enhanced bioavailability of polyaromatic hydrocarbons in the form of mucin complexes. Belgorodsky, B; Drug, E; Ermakov, N; Fadeev, L; Frenkel-Pinter, M; Gozin, M; Landesman-Milo, D; Peer, D, 2011)	0.37
" However, poor bioavailability following ingestion limits their efficacy in vivo."	( Sustained systemic delivery of green tea polyphenols by polymeric implants significantly diminishes benzo[a]pyrene-induced DNA adducts. Cai, J; Cao, P; Gupta, RC; Spencer, WA; Vadhanam, MV, 2011)	0.37
"Oral formulations of 5-fluorouracil (5-FU) with enhanced bioavailability were developed using microemulsion as a drug carrier system."	( Development and evaluation of novel microemulsion based oral formulations of 5-fluorouracil using non-everted rat intestine sac model. Maheshwari, M, 2012)	0.38
" However, biodegradation of BaP has been limited because of its bioavailability and toxicity."	( Fate and cometabolic degradation of benzo[a]pyrene by white-rot fungus Armillaria sp. F022. Hadibarata, T; Kristanti, RA, 2012)	0.38
") Thus, overall results suggest that nano-encapsulation of PD (NPD) increases drug bioavailability and thereby has a better chemo-preventive action against lung cancer in vivo and on A549 cells in vitro than that of PD."	( Poly (lactide-co-glycolide) encapsulated extract of Phytolacca decandra demonstrates better intervention against induced lung adenocarcinoma in mice and on A549 cells. Bhadra, K; Das, J; Das, S; Khuda-Bukhsh, AR; Samadder, A, 2012)	0.38
" Therefore, establishing numeric chronic toxicity thresholds for sediment-associated BaP with the consideration of the bioavailability would improve the accuracy of assessing PAH-related sediment toxicity."	( Chronic toxicity thresholds for sediment-associated Benzo[a]pyrene in the Midge (Chironomus dilutus). Du, J; Huang, ZC; Li, Y; You, J, 2014)	0.4
" The enhanced PAHs degradation in FCOM-amended sediments was related to higher PAH-degrading bacteria number and bioavailability with a result of biostimulation and priming effect by labile carbon and high-value nutrition in FCOM."	( Accelerated removal of pyrene and benzo[a]pyrene in freshwater sediments with amendment of cyanobacteria-derived organic matter. Jiang, H; Li, X; Shi, Y; Yan, Z, 2014)	0.4
"Oral bioavailability of benzo[a]pyrene (B[a]P) was studied in a swine model using eight spiked soil samples after incubation for 50 and/or 90 days."	( Effects of ageing and soil properties on the oral bioavailability of benzo[a]pyrene using a swine model. Dong, Z; Duan, L; Kuchel, T; Liu, Y; Mallavarapu, M; Naidu, R; Palanisami, T; Semple, KT, 2014)	0.4
" Pharmacokinetics analysis showed good bioavailability of PPP in lung and plasma."	( Targeting the insulin-like growth factor-1 receptor by picropodophyllin for lung cancer chemoprevention. Lubet, RA; Pan, J; Wang, Y; You, M; Zhang, Q, 2015)	0.42
" Subjects with reduced ABCG2 or ABCC2 expression might have higher oral bioavailability for BP due to a reduced excretion and so might be more susceptible to BP-induced carcinogenesis."	( The role of the efflux carriers Abcg2 and Abcc2 for the hepatobiliary elimination of benzo[a]pyrene and its metabolites in mice. Aretz, J; Geyer, J; Hessel, S; Kranz, J; Lampen, A; Petzinger, E; Seidel, A, 2014)	0.4
" In this study we investigated effects of titanium dioxide nanoparticles (TiO2NP) on the blue mussel (Mytilus edulis) and determined their influence on the bioavailability and toxicity of benzo(a)pyrene (B(a)P), a carcinogenic polyaromatic hydrocarbon (PAH)."	( The impact of TiO2 nanoparticles on uptake and toxicity of benzo(a)pyrene in the blue mussel (Mytilus edulis). Bączek, T; Bergum, S; Ciesielski, TM; Farkas, J; Jenssen, BM; Konieczna, L; Nilsen, EW; Olsen, AJ; Salaberria, I; Salvenmoser, W, 2015)	0.85
"Polycyclic aromatic hydrocarbon (PAH) bioavailability from ingested soils will vary between soils; however, the nature of this variation is not well characterized."	( Is received dose from ingested soil independent of soil PAH concentrations?-Animal model results. Cave, M; James, K; Peters, RE; Siciliano, SD; Wickstrom, M, 2016)	0.43
"56), which indicated that ASE extraction techniques could not predict PAHs bioavailability to earthworms because it overestimated the risk of PAHs."	( [Aging Law of PAHs in Contaminated Soil and Their Enrichment in Earthworms Characterized by Chemical Extraction Techniques]. Bian, YR; Gu, CG; Jiang, X; Li, J; Liu, ZT; Wang, DZ; Yang, XL; Zhang, YN, 2015)	0.42
"We compare B[a]P bioavailability using a rat model to that estimated in a swine model, to investigate the correlation between these two animal models."	( Comparison of oral bioavailability of benzo[a]pyrene in soils using rat and swine and the implications for human health risk assessment. Dong, Z; Duan, L; Herde, P; Kuchel, T; Liu, Y; Mallavarapu, M; Naidu, R; Semple, KT, 2016)	0.43
" B[a]P bioavailability was estimated by the area under the plasma B[a]P concentration-time curve (AUC) and faecal excretion as well in the rats."	( Comparison of oral bioavailability of benzo[a]pyrene in soils using rat and swine and the implications for human health risk assessment. Dong, Z; Duan, L; Herde, P; Kuchel, T; Liu, Y; Mallavarapu, M; Naidu, R; Semple, KT, 2016)	0.43
" However, absolute bioavailability was significantly higher when using faecal excretion assay (p<0."	( Comparison of oral bioavailability of benzo[a]pyrene in soils using rat and swine and the implications for human health risk assessment. Dong, Z; Duan, L; Herde, P; Kuchel, T; Liu, Y; Mallavarapu, M; Naidu, R; Semple, KT, 2016)	0.43
"The objective of this study was to examine the influence of soil composition, PAH concentration, and source material type on PAH bioavailability using an approach capable of measuring uptake at low, environmentally relevant PAH concentrations (down to 1 ppm)."	( Effects of Source and Concentration on Relative Oral Bioavailability of Benzo(a)pyrene from Soil. Lowney, Y; Munson, JW; Roberts, SM; Ruby, MV, 2016)	0.67
" This role has not been conclusively determined to date because CBNs can decrease the bioavailability of contaminants or represent an additional source of intake."	( Carbon nanopowder acts as a Trojan-horse for benzo(α)pyrene in Danio rerio embryos. Armini, A; Ascagni, M; Binelli, A; Bini, L; Del Giacco, L; Della Torre, C; Ghilardi, A; La Porta, C; Landi, C; Madaschi, L; Maggioni, D; Magni, S; Parolini, M; Prosperi, L; Santo, N, 2017)	0.46
" Correspondingly, chemical analysis of the system showed that these genetic changes resulted in increases in the levels of easily oxidizable organic carbon and humic acids which may have resulted in increased BaP bioavailability and increased degradation rates."	( Interconnection of Key Microbial Functional Genes for Enhanced Benzo[a]pyrene Biodegradation in Sediments by Microbial Electrochemistry. Cai, H; He, Y; He, Z; Jiang, HL; Krumholz, LR; Van Nostrand, JD; Yan, Z; Zhou, J, 2017)	0.46
" An orthogonal design experiment revealed that BaP biodegradation was greatly enhanced by surfactants such as Tween 80, Triton X-100 and linoleic acid, suggesting that bioavailability is the major limiting factor in bacterial metabolism of BaP."	( Biodegradation of high-molecular weight PAHs by Rhodococcus wratislaviensis strain 9: Overexpression of amidohydrolase induced by pyrene and BaP. Megharaj, M; Naidu, R; Subashchandrabose, SR; Venkateswarlu, K, 2019)	0.51
" Adsorption of BaP to F-MWCNTs could mitigate the bioavailability and toxicity of BaP in biological systems."	( Individual and combined toxicity of carboxylic acid functionalized multi-walled carbon nanotubes and benzo a pyrene in lung adenocarcinoma cells. Khodagholi, F; Mehrabi, Y; Mohammadian, Y; Omidi, M; Peirovi, H; Pourahmad, J; Rafieepour, A; Rezazadeh Azari, M, 2019)	0.51
" In addition, the absorption rate of naphthalene and phenanthrene by keratinocytes was higher than that of pyrene and benzo[a]pyrene, with the latter being of higher molecular weight."	( Dermal bioaccessibility and absorption of polycyclic aromatic hydrocarbons (PAHs) in indoor dust and its implication in risk assessment. Chen, Z; Kang, Y; Li, C; Li, H; Lin, X; Luo, K; Man, YB; Sun, N; Zeng, D; Zhu, M, 2020)	0.56
" Cyp1a induction and fluorescent analyses proved BaP bioavailability after transfer via Paramecium and Artemia."	( Microplastics and sorbed contaminants - Trophic exposure in fish sensitive early life stages. Batel, A; Bégout, ML; Braunbeck, T; Bringer, A; Cousin, X; Hess, S, 2020)	0.56
" However, the mechanism of mobilization of hydrophobic compounds by non-motile microorganisms such as filamentous fungi needs investigations to improve pollutant bioavailability and bioremediation efficiency."	( A compartmentalized microsystem helps understanding the uptake of benzo[a]pyrene by fungi during soil bioremediation processes. Baranger, C; Deleu, M; Fayeulle, A; Le Goff, A; Lins, L; Pezron, I, 2021)	0.62
" These findings indicate that omega GST may play an important role in the phase II detoxification of PAHs in polychaete worms, and the persistence and bioavailability of PAHs may depend on benzene rings."	( Expression profile of a novel glutathione S-transferase gene in the marine polychaete Perinereis aibuhitensis in short-term responses to phenanthrene, fluoranthene, and benzo[α]pyrene. Li, D; Ma, X; Wang, L; Wang, Y; Yang, D; Yang, X; Yuan, X; Zhang, A; Zhao, H; Zhou, Y, 2021)	0.62
"There is a strong need for certified reference materials in the quality assurance of nonionic soil contaminant bioavailability estimations through physicochemical methods."	( Determining the bioavailability of benzo(a)pyrene through standardized desorption extraction in a certified reference contaminated soil. Ortega-Calvo, JJ; Posada-Baquero, R; Semple, KT; Ternero, M, 2022)	1
" Furthermore, the evolution of organic matter pools in terms of accessibility and complexity may drive the bioavailability of these pollutants, leading to their significant removal."	( Combining sequential extraction and 3D fluorescence to investigate the behavior of antibiotic and polycyclic aromatic hydrocarbons during solar drying of sewage sludge. An-Nori, A; Barret, M; Bousquet-Melou, A; El Fels, L; El Gharous, M; El Mejahed, K; Ezzariai, A; Hafidi, M; Kouisni, L; Lacroix, MZ; Merlina, G; Patureau, D; Pinelli, E; Riboul, D, 2022)	0.72
" Use of alternative and short-term toxicity testing methods, improved mixture characterization, understanding the fate and bioavailability of PAH mixtures, and understanding exposure route-related differences in carcinogenicity are discussed as ways to improve the understanding of the risks of PAHs."	( The Long Goodbye: Finally Moving on from the Relative Potency Approach to a Mixtures Approach for Polycyclic Aromatic Hydrocarbons (PAHs). Haber, LT; Pecquet, AM; Vincent, MJ; White, LM, 2022)	0.72
" This work revealed that the bioavailability of G-Rg3 was relatively poor."	( The preventive role of the red gingeng ginsenoside Rg3 in the treatment of lung tumorigenesis induced by benzo(a)pyrene. Fei, S; Liu, L; Xiong, J; Yang, S; You, M; Yuan, H, 2023)	1.12
" Due to its high surface to volume ratio, GO can adsorb persistent organic pollutants (POPs), such as benzo(a)pyrene (BaP), and act as carrier of POPs, increasing their bioavailability to marine organisms."	( Fate and effects of graphene oxide alone and with sorbed benzo(a)pyrene in mussels Mytilus galloprovincialis. Bilbao, E; Blasco, N; Cajaraville, MP; González-Soto, N; Guilhermino, L; Irazola, M, 2023)	1.37
" In addition, the bioavailability analysis results demonstrated that the water- and butanol-extractable BaP increased with elevated temperatures."	( Thermally enhanced biodegradation of benzo[a]pyrene and benzene co-contaminated soil: Bioavailability and generation of ROS. Ali, M; Chen, X; Liu, X; Song, X; Tang, Z; Wang, Q; Zhang, M; Zhang, Z, 2023)	0.91
"The limited bioavailability of polycyclic aromatic hydrocarbons (PAHs) in soils poses a challenge for their biodegradation."	( Degradation of benzo [a] pyrene in the soil enhanced by soapwort: The role of soapwort and functional microbial community. Dai, W; Liu, Y; Tian, K; Wang, H; Wang, N; Yao, D, 2023)	0.91

Excerpt	Relevance	Reference
" A mathematical estimation of the risk caused by a certain height of exposure is usually done under the assumption of a linear dose-response relationship by means of an arithmetical factor which gives the ratio of risk to dose in the low-response range and which has to be found on the basis of epidemiological or experimental data."	( [Methods of risk assessment from data of experimental carcinogenesis studies]. Csicsaky, M; Pott, F; Roller, M, 1992)	0.28
" The mutagenic activities were calculated by least squares linear regression from the slope of the linear portion of each dose-response curve."	( Results of a comparative study on the Salmonella pre-incubation and plate incorporation assays using test samples from the IPCS collaborative study. Endo, O; Goto, S; Matsushita, H, )	0.13
" cyanellus) were dosed per os with allyl formate (ALF) and carbon tetrachloride (CCl4), and the induction of liver EROD (7-ethoxyresorufin O-deethylase) activity was subsequently challenged by injections of beta-naphthoflavone (BNF) and benzo[a]pyrene (B[a]P)."	( Effects of hepatotoxicants on the induction of microsomal monooxygenase activity in sunfish liver by beta-naphthoflavone and benzo[a]pyrene. Jimenez, B; Oikari, A, 1992)	0.28
" Mice were dosed with a daily sc dose of 200 mg/kg B(a)P or vehicle for 4 days."	( Evaluation of murine splenic cell type metabolism of benzo[a]pyrene and functionality in vitro following repeated in vivo exposure to benzo[a]pyrene. Kawabata, TT; Ladics, GS; Munson, AE; White, KL, 1992)	0.28
" Dose-response studies demonstrated a positive relationship between BPDE-DNA adduct formation, the immunocytochemical staining signal and the BPDE concentration in the culture medium."	( Immunocytochemical visualization of DNA adducts in mouse tissues and human white blood cells following treatment with benzo[a]pyrene or its diol epoxide. A quantitative approach. den Engelse, L; Hillebrand, MJ; Kriek, E; Scherer, E; van Schooten, FJ, 1991)	0.28
" In the dose-response study, a dose-related inhibition of the mitomycin C (MMC)-induced MPCE frequency by estradiol (E2) treatment was observed."	( Effect of estrogen on induction of micronuclei by mutagens in male mice. Miyamoto, H; Nagae, Y; Shimizu, H; Suzuki, Y, 1991)	0.28
" The retention in tissues, extent of DNA adduct formation in liver and intestine, and metabolite composition of bile was investigated in southern flounder following gavage with pure [3H]- or [14C]benzo[a]pyrene (BaP), pure [14C]benzo[a]pyrene-7,8-dihydrodiol (BaP-7,8D), or hepatopancreas from spiny lobsters previously dosed with [3H]- or [14C]BaP (Metab."	( Southern flounder hepatic and intestinal metabolism and DNA binding of benzo[a]pyrene (BaP) metabolites following dietary administration of low doses of BaP, BaP-7,8-dihydrodiol or a BaP metabolite mixture. Altman, AH; Boyle, SM; Cromer, EA; James, MO; Schell, JD, 1991)	0.28
"A factorial experimental design was used within this study to evaluate the influence of multiple metabolic activation system concentrations on the dose-response exhibited by promutagens (indirect-acting mutagens) in the Salmonella spiral and plate assays."	( Evaluating the relationship of metabolic activation system concentrations and chemical dose concentrations for the Salmonella spiral and plate assays. Allison, JC; Claxton, LD; Creason, J; Houk, VS, 1991)	0.28
" BaP-tetrol levels were measured in rats dosed intraperitoneally with 242, 71 and 24 mumol BaP kg-1 body weight in corn oil."	( Globin adducts of benzo[a]pyrene: markers of inhalation exposure as measured in F344/N rats. Bechtold, WE; Bond, JA; Griffith, WC; Kilmer, JW; Sun, JD; Wolff, RK, 1991)	0.28
" The substantial cell killing and regenerative proliferation, and the correspondence between the dose-response patterns for epidermal damage and tumors, together with the initial appearance of tumors in the benign form, a characteristic of the action of promoting agents, provided evidence that the tissue damage associated with the high dose levels of B[a]P used in this study reflected tumor-promoting activity in this mouse epidermal tumorigenesis model."	( Benzo[a]pyrene-induced skin damage and tumor promotion in the mouse. Albert, RE; Andringa, A; Baxter, CS; Cody, T; Miller, ML; Shukla, R, 1991)	0.28
" The dose-response curves for all compounds show a plateau with higher exposures."	( Drosophila wing-spot test: improved detectability of genotoxicity of polycyclic aromatic hydrocarbons. Frölich, A; Würgler, FE, 1990)	0.28
" EMS was examined in the absence of any exogenous metabolic activation system, and the mutagenic dose-response obtained served to calibrate the assay."	( Mutation assays of ethyl methanesulphonate, benzidine and benzo[a]pyrene using Chinese hamster V79 cells. O'Donovan, MR, 1990)	0.28
" helix showed antimutagenic activity against BaP (1 microgram) and SU (5 microliters) with a dose-response relationship."	( Antimutagenic activity of some saponins isolated from Calendula officinalis L., C. arvensis L. and Hedera helix L. Balansard, G; De Méo, M; Dumenil, G; Elias, R; Laget, M; Vidal-Ollivier, E, 1990)	0.28
"Mice were exposed to benzo(a)pyrene at a dosage of 50, 100 and 200 micrograms/g by single intraperitoneal injection route."	( [Effects of benzo(a)pyrene on the humoral immunity of mice exposed by single intraperitoneal injection]. Zhao, XL, 1990)	0.98
" Parallelism of dose-response curves of different materials and quantitative reproducibility of dermal carcinogenesis data were also examined."	( Estimation of epidermal carcinogenic potency. Lewis, SC; McKee, RH; Nicolich, MJ; Scala, RA, 1990)	0.28
" Viral interferon induction was inhibited in a dose-response manner by B[a]P (+/- S9) in combination with selected particles."	( Coinhibition of viral interferon induction by benzo[a]pyrene in association with occupation-related particles. Booth, JA; Flowers, L; Hahon, N, 1990)	0.28
" Twenty-four hours after administration of B[a]P or diesel particulate extract, the AHH activity increased in a dose-response manner in the lung, but not in liver."	( Induction of aryl hydrocarbon hydroxylase in rat tissue following intratracheal instillation of diesel particulate extract and benzo[a]pyrene. Chen, KC, 1986)	0.27
" In a dose-response study, 7-ethoxyresorufin O-deethylase (EROD) activity appeared to be maximally induced in C57BL/6J and DBA/2J mice at 7 days following exposure to 3 and 30 micrograms of TCDD/kg respectively."	( Biphasic response for hepatic microsomal enzyme induction by 2,3,7,8-tetrachlorodibenzo-p-dioxin in C57BL/6J and DBA/2J mice. Guengerich, FP; Olson, JR; Shen, ES, 1989)	0.28
" We determined whether electrophilic metabolites could be detected in mouse serum 4 h after BaP dosing (i."	( Transport of DNA-adducting metabolites in mouse serum following benzo[a]pyrene administration. Atherholt, TB; Ginsberg, GL, 1989)	0.28
" BaP induced similar, but not identical, SCE dose-response curves for each species."	( Sensitivity of rat and mouse peripheral blood lymphocytes to BaP adduction and SCE formation. Earley, K; Erexson, GL; Gupta, RC; Kligerman, AD; Nesnow, S, 1989)	0.28
" The integral role of S9 for BaP bioactivation and the resultant inhibition of viral IFN induction was substantiated by dose-response relationships, time-dependency of effects, and reversibility of adverse reactivity."	( Benzo[a]pyrene: kinetics of in vitro bioactivation in relation to inhibition of viral interferon induction. Booth, JA; Hahon, N, 1988)	0.27
" The induction rate of CA in the cells of the fish species exposed to the chemicals tested for 48 hr clearly shows not only an increase in the CA frequency in a dose-response manner above the control, but also a species response dependency."	( Carcinogenic-mutagenic chemicals induced chromosomal aberrations in the kidney cells of three cyprinids. Al-Sabti, K, 1985)	0.27
" By convolution calculation, with in vitro desorption as input function and the disposition of B(a)P dosed intratracheally to the lung in an alveolar surfactant solution as reference, hypothetical areas under B(a)P buffer concentration vs."	( Bioavailability of benzo(a)pyrene deposited in the lung. Correlation with dissolution from urban air particulates and covalently bound DNA adducts. Nicklasson, M; Nybom, L; Söderkvist, P; Toftgård, R; Törnquist, S, )	0.46
" These results correlated closely with the dose-response relationships for tumor initiation by the two hydrocarbons."	( Correlation between formation of a specific hydrocarbon-deoxyribonucleoside adduct and tumor-initiating activity of 7,12-dimethylbenz(a)anthracene and its 9- and 10-monofluoroderivatives in mice. DiGiovanni, J; Fisher, EP; Sawyer, TW, 1986)	0.27
" The liver microsomal metabolism of n-hexane increased to about the same extent at all dosage levels."	( Phthalate esters: effects of orally administered dibutylphthalate on cytochrome P-450 mediated metabolism in rat liver and lung. Nilsen, OG; Walseth, F, 1986)	0.27
" Analyses of dose-response curves suggest (i) CuDIPS preferentially inhibits BP mutagenesis; (ii) the antimutagenic activity of CuDIPS towards DMBA and the cytotoxicity of the copper complex are derived from the DIPS component of the chelate; (iii) the antimutagenic activity of CuDIPS towards BP requires both copper and DIPS; and (iv) DIPS and CuDIPS induced cytotoxicity is required for inhibition of mutagenesis."	( Survey of cytotoxicities and antimutagenic and antitumor initiating activities of Cu(II)(3,5-diisopropylsalicylate)2 and its analogs in a keratinocyte-mediated mutation assay and the murine skin multistage carcinogenesis model. Colby, AB; Reiners, JJ, 1988)	0.27
"55 mumol) with the dose-response relationship indicating a saturation of tumor multiplicity at approximately 7 tumors/animal."	( Dose-response relationships of the tumorigenicity of cyclopenta[cd]pyrene, benzo[a]pyrene and 6-nitrochrysene in a newborn mouse lung adenoma bioassay. Busby, WF; Cornelisse, J; Kellenbach, ER; Lugtenburg, J; Stevens, EK, 1988)	0.27
" The dose-response curves for the induction of hepatic microsomal AHH by 3-methylcholanthrene (MC) were indistinguishable in both +4S and -4S rats and comparable results were observed for 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) as an inducer."	( Role of the 4-5S binding protein in the induction of aryl hydrocarbon hydroxylase in the rat. Harris, M; Kamps, C; Safe, S, 1988)	0.27
" Antibody responses which are suppressed in BaP dosed mice can be reconstituted in vitro by the addition of exogenous interleukin-1."	( Modulation of interleukin-1 production by macrophages following benzo(a)pyrene exposure. Bick, PH; Lyte, M, 1986)	0.51
"Rats, germfree and conventional, were dosed with 14C-labelled benzo[a]pyrene."	( Studies on the chromatographic fractionation of metabolites of benzo[a]pyrene in faeces and urine from germfree and conventional rats. Egestad, B; Gustafsson, JA; Hyvönen, K; Pettersson, P; Rafter, J; Sjövall, J, 1987)	0.27
" Animals dosed for 7 days with 13cisRA, retinyl acetate, or 4HPR showed a 38, 27, and 40% reduction in binding of benzo(a)pyrene to liver DNA and a 29, 32, and 21% reduction in binding to stomach DNA, respectively, when the carcinogen was administered on the eighth day, and the tissues were harvested 24 h later."	( Effects of retinoids on metabolizing enzymes and on binding of benzo(a)pyrene to rat tissue DNA. Hill, DL; Lindamood, C; McCarthy, DJ, 1987)	0.72
" The same oil was then examined in combination with benzo(a)pyrene (BaP) and, from the dose-response obtained, it was clear that the oil did not prevent BaP induced nuclear enlargement."	( Nuclear enlargement produced in mouse skin by carcinogenic mineral oils. Grasso, P; Ingram, AJ, 1987)	0.52
" Inhibition of AHH activity was still present 24 h after dosing (41%)."	( Lung metabolism of benzo[a]pyrene in rats treated with p-xylene and/or ethanol. Bogdanffy, MS; Brown, DR; Roberts, AE; Schatz, RA, 1986)	0.27
" Low levels of covalent binding of 3H to DNA of liver and gut mucosa were obtained in guinea-pigs dosed orally with 3H-benzo[a]pyrene."	( The intestinal metabolism and DNA binding of benzo[a]pyrene in guinea-pigs fed normal, high-fat and high-cholesterol diets. Bowes, SG; Renwick, AG, 1986)	0.27
" Similarly, the topical application of 2,500 nmol of ellagic acid at 2 h, 1 h and 5 min before and at 10 min after the application of 2 nmol of [3H]B[a]P did not inhibit the formation of DNA-bound adducts, but the same dosing regimen of 3-O-decylellagic acid (total dose of 10,000 nmol) resulted in a modest inhibition in the formation of DNA-bound adducts."	( Effect of ellagic acid and 3-O-decylellagic acid on the formation of benzo[a]pyrene-derived DNA adducts in vivo and on the tumorigenicity of 3-methylcholanthrene in mice. Chang, RL; Conney, AH; Huang, MT; Jerina, DM; Sayer, JM; Smart, RC; Wood, AW, 1986)	0.27
" The same dosage levels of BP and methadone were also given to pseudopregnant rats (PSP) with an induced decidual cell reaction (DCR) in an attempt to distinguish whether adverse effects occur in the maternal or fetal compartment or both."	( A comparative study of the reproductive effects of methadone and benzo[a]pyrene in the pregnant and pseudopregnant rat. Bui, QQ; Tran, MB; West, WL, 1986)	0.27
" Dose-response curves did show reduction of CSC- and BaP-induced mutagenicity by ellagic acid, riboflavin and chlorophyllin."	( Antimutagenic activity of some naturally occurring compounds towards cigarette-smoke condensate and benzo[a]pyrene in the Salmonella/microsome assay. Terwel, L; van der Hoeven, JC, 1985)	0.27
" Dose-response curves for mutagenicity of quercetin with or without AAF (5 micrograms/plate) were examined."	( The effect of quercetin on the mutagenicity of 2-acetylaminofluorene and benzo[alpha]pyrene in Salmonella typhimurium strains. Fukui, S; Hirai, K; Hirayama, T; Nohara, M; Ogawa, S; Tokuda, M, 1985)	0.27
" Dose-response relationships were obtained for NMU and NC as well as for BaP."	( Local application to mouse skin as a carcinogen specific test system for non-volatile nitroso compounds. Brune, H; Deutsch-Wenzel, RP; Grimmer, G; Misfeld, J, 1985)	0.27
"This work is a graphical study of all known dose-response data for neoplasia induced by B(a)P, benzene, benzidine, and chromium administered to test animals."	( Animal studies and prediction of human tumors can be aided by graphical sorting of animal data: neoplastic risk from B(a)P, benzene, benzidine, and chromium. Jones, TD; Walsh, PJ, 1985)	0.27
" Besides, dependence of theophylline elimination rate constant on the time of chrysene dosing was also shown."	( The effect of chrysene and some polycyclic aromatic hydrocarbons on the elimination of theophylline in rats. Brandys, J; Piekoszewski, W, 1985)	0.27
" By comparing dose-response curves obtained with three protocols which overcome the optical and cytochemical difficulties of sperm measurement in different ways we conclude the response is due to X-ray-induced DNA content variability."	( Radiation-induced DNA content variability in mouse sperm. Gledhill, BL; Lake, S; Pinkel, D; Van Dilla, MA; Wyrobek, AJ, 1983)	0.27
" Time-response and dose-response were studied for chromosomal aberrations induced by transplacental treatment of mouse embryos."	( New approaches to mutagenicity studies in animals for carcinogenic and mutagenic agents. II. Clastogenic effects determined in transplacentally treated mouse embryos. Adler, ID, 1983)	0.27
" The tumor incidence demonstrated a clear-cut dose-response relationship."	( Contribution of polycyclic aromatic hydrocarbons to the carcinogenic impact of gasoline engine exhaust condensate evaluated by implantation into the lungs of rats. Brune, H; Dettbarn, G; Deutsch-Wenzel, R; Grimmer, G; Misfeld, J, 1984)	0.27
" However, at low BP dosage (0."	( Effect of visible light on benzo(a)pyrene binding to DNA of cultured human skin epithelial cells. Baeck, AE; Camalier, RF; Gantt, R; Price, FM; Sanford, KK; Stephens, EV; Taylor, WG, 1981)	0.56
" This reverse dose-response may be due to the relatively high cytotoxicity of CPEP, BP, which was compared to CPEP at the low dose, elicited tumors in 100% of the mice."	( Carcinogenicity of the environmental pollutants cyclopenteno-[cd]pyrene and cyclopentano[cd]pyrene in mouse skin. Cavalieri, E; Munhall, A; Rogan, E; Toth, B, 1981)	0.26
" A positive dose-response relationship in transformation by benzo[a]pyrene occurred."	( Equivalency of endothelial cell growth supplement to irradiated feeder cells in carcinogen-induced morphologic transformation of Syrian hamster embryo cells. DiPaolo, JA; Evans, CH, 1982)	0.26
" Dose-response studies in which benzo[a]pyrene-deoxyguanosine adducts were quantified by enzyme-linked immunosorbent assay and compared with intensity of immunofluorescence demonstrated that decreasing doses of the carcinogen resulted in fewer numbers of adducts as well as proportionally less fluorescence."	( Indirect immunofluorescent localization of benzo[a]pyrene adducted to nucleic acids in cultured mouse keratinocyte nuclei. Beckwith, JB; Poirier, MC; Stanley, JR; Weinstein, IB; Yuspa, SH, 1982)	0.26
" For both BP and DMN the human cells and the CHO cells showed dose-response slopes that were significantly different from zero, except CHO cells treated with BP for 1 hr and S-3299 cells treated with DMN."	( Sister chromatid exchange response of human diploid fibroblasts and Chinese hamster ovary cells to dimethylnitrosamine and benzo(a)pyrene. Biggs, D; Douglas, GR; Kwok, SE; Tomkins, DJ, 1982)	0.47
" Dose-response curves for fertility reduction and primordial oocyte destruction were identical."	( The effect of benzo(a)pyrene on fertility, primordial oocyte number, and ovarian response to pregnant mare's serum gonadotropin. Mattison, DR; Nightingale, MR; White, NB, 1980)	0.62
" The tumor-initiating activity of B(a)P, its covalent binding to mouse epidermal DNA, and the formation of the major hydrocarbon/deoxyribonucleoside adduct showed approximately parallel dose-response curves."	( Formation of benzo(a)pyrene/DNA adducts and their relationship to tumor initiation in mouse epidermis. Ashurst, SW; Cohen, GM; DiGiovanni, J; Nesnow, S; Slaga, TJ, 1983)	0.64
" Subsequent studies on placentas derived from 67 women who smoked 10 to 40 cigarettes per day demonstrated a definite dose-response relationship between AHH activity and the number of cigarettes smoked/day."	( Population distribution of placental benzo(a)pyrene metabolism in smokers. Bansal, SK; Caballes, L; Gottlieb, K; Gurtoo, HL; Marinello, AJ; Mulhern, AI; Vaught, JB; Williams, CJ, 1983)	0.54
" In both stomach and liver, the formation of acid-hydrolyzable and non-acid-hydrolyzable BP-DNA adducts was linearly related to dose, over a carcinogen dosage range of 10(-8) to 10(-3) g (liver) or 10(-7) to 10(-3) g (stomach)."	( Wide-range linear dose-response curve for DNA binding of orally administered benzo(a)pyrene in mice. Dunn, BP, 1983)	0.49
" In lung and liver of untreated animals, the dose-response curves for BPDEI:DNA adduct levels were sigmoidal."	( Dose-response relationships for the binding of benzo(a)pyrene metabolites to DNA and protein in lung, liver, and forestomach of control and butylated hydroxyanisole-treated mice. Adriaenssens, PI; Anderson, MW; White, CM, 1983)	0.52
" A transforming dose-response curve is achieved but the frequency of transformation is less than half the expected for 38 d foci, compared on the basis of percent transformants per cell plated."	( Colony transformation in C3H 10T1/2 cells: stepwise development of neoplastic change in vitro. Garry, VF; Nelson, RL, 1983)	0.27
" Animals were treated with a dosage regimen of aspirin which inhibited PES but had no effect on the cytochrome P-450-dependent oxidation of 7,8-dihydrodihydroxybenzo(a)pyrene."	( Effect of aspirin and indomethacin on the formation of benzo(a)pyrene-induced pulmonary adenomas and DNA adducts in A/HeJ mice. Adriaenssens, PI; Anderson, MW; Boorman, GA; Eling, TE; Sivarajah, K, 1983)	0.71
" The induction of SCEs followed a dose-response pattern with plateaus at high doses of PAH."	( Activation of polycyclic hydrocarbons in Reuber H4-II-E hepatoma cells. An in vitro system for the induction of SCEs. Bynum, G; Dean, RG; Hadley, E; Jacobson-Kram, D, 1983)	0.27
" The research of the relations is intricate because no simple dose-response relations are existing between environmental influence and population."	( [Importance of atmospheric air pollution in the development of diseases]. Horn, K, 1983)	0.27
" Time-course and dose-response studies in C57BL/6Ha mice revealed that the metabolism of aflatoxin B1/B2 to aflatoxin M1/M2 (AFB1/B2-4-hydroxylase activity) was induced by both MC and beta NF."	( Genetic expression of aflatoxin metabolism. Effects of 3-methylcholanthrene and beta-naphthoflavone on hepatic microsomal metabolism and mutagenic activation of aflatoxins. Gurtoo, HL; Raina, V; Williams, CJ, 1983)	0.27
" Dose-response relationships were obtained for DBa,hAC as well as for BaP."	( Experimental studies on the carcinogenicity of five nitrogen containing polycyclic aromatic compounds directly injected into rat lungs. Brune, H; Deutsch-Wenzel, RP; Grimmer, G, 1983)	0.27
"3 mg, single dosage per mouse) and 2-bromoethanol in 2 dosages (1."	( [Carcinogenic activity of ethylene oxide and its reaction products 2-chlorethanol, 2-bromoethanol, ethylene glycol and diethylene glycol. II. Testing of 2-chlorethanol and 2-bromoethanol for carcinogenic activity]. Dunkelberg, H, 1983)	0.27
" In this case the effective dosage was equivalent to an air volume of 2-5 cbm."	( [Biological effect of smog extract. VII. Severe disorders of the cell cycle and its phases in kidney cultures as effected by extract and fractions of smog from a heavily industrialized area]. Behmer, A; Seemayer, NH, 1983)	0.27
" The dose-response patterns differed completely between CSCs and BaP."	( Toxic and transforming effects of cigarette smoke condensates in fetal Syrian golden hamster lung cell cultures. Emura, M; Mohr, U, 1983)	0.27
" The tumor incidence exhibited a clear cut dose-response relationship."	( The contribution of polycyclic aromatic hydrocarbons to the carcinogenic impact of emission condensate from coal-fired residential furnaces evaluated by topical application to the skin of mice. Abel, U; Brune, H; Dettbarn, G; Deutsch-Wenzel, R; Grimmer, G; Misfeld, J; Timm, J, 1984)	0.27
" BP dose-response studies showed that, in cells of different maturation states, BP-DNA adduct levels were similar."	( Benzo(a)pyrene-DNA adduct formation and removal in mouse epidermis in vivo and in vitro: relationship of DNA binding to initiation of skin carcinogenesis. Nakayama, J; Poirier, MC; Yuspa, SH, 1984)	1.71
" One hundred thirty-seven animals survived the dosing period."	( The effect of diethylhydroxylamine on the incidence of tumors induced by benzo(a)pyrene in the mouse. Heicklen, J; Massaro, EJ; Miller, GD; Wilson, T, 1984)	0.5
" The probit and Weibull analysis of the results showed a linear dose-response relationship for both tumor incidences and tumor induction times."	( Investigation on the carcinogenicity of emission condensate from brown coal-fired residential furnaces applied to mouse skin. Brune, H; Dettbarn, G; Deutsch-Wenzel, RP; Grimmer, G; Misfeld, J; Timm, J, 1984)	0.27
" The highest frequency of micronuclei and dose-response relationship between PGE2 doses and micronucleus frequency were observed 30 h after injection of MMC to mice administered PGE2 24 h previously."	( Effects of prostaglandin E2 on the micronucleus formation in mouse bone marrow cells by various mutagens. Fukumoto, M; Ishikawa, T; Kadokura, M; Okonogi, H; Sakaba, H; Shimizu, H; Suzuki, Y, 1994)	0.29
"The traditional multistage (MS) model of carcinogenesis implies several empirically testable properties for dose-response functions."	( An exact analysis of the multistage model explaining dose-response concavity. Cox, LA, 1995)	0.29
" Similarly, sum total of free (+)-anti-benzo[a]pyrene-7,8-dihydrodiol-9,10-epoxide, glutathione conjugates and DNA-bound metabolites formed from precursor (-)-7R-trans-benzo[a]pyrene-7,8-dihydrodiol showed marked reduction in both the male and female ferrets after ETS exposure in a dose-response manner."	( Depression of hepatic cytochrome P450 monooxygenases after chronic environmental tobacco smoke exposure of young ferrets. Fujita, I; Kikkawa, Y; Rasmussen, RE; Sindhu, RK; Yamamoto, R, 1995)	0.29
" Studies with the intact lung and with isolated lung cells show that carcinogen metabolism and pharmacokinetics depend both on the route of exposure and dosage and on the distribution of specific enzymes."	( Effects of induction and age-dependent enzyme expression on lung bioavailability, metabolism, and DNA binding of urban air particulate-absorbed benzo[a]pyrene, 2-nitrofluorene, and 3-amino-1,4-dimethyl-5H-pyridol-(4,3)-indole. Gøtze, JP; Lindeskog, P; Törnquist, CS, 1994)	0.29
" Dose-response relations between total PAH, pyrene, carcinogenic PAHs, and 1-hydroxypyrene for smokers, and polycyclic aromatic hydrocarbons adsorbed to dust for non-smokers are suggested."	( Exposure of iron foundry workers to polycyclic aromatic hydrocarbons: benzo(a)pyrene-albumin adducts and 1-hydroxypyrene as biomarkers for exposure. Autrup, H; Hansen, AM; Omland, O; Overgaard, E; Sherson, D; Sigsgaard, T, 1994)	0.52
" BPDE-DNA adducts reached their maximum at 24 h after all dosage regimens, but were very well detectable also at 12 and 48 h after the treatment, while no adducts were measurable at 1 week and thereafter."	( Benzo[a]pyrene-7,8-diol-9,10-epoxide-DNA adducts and increased p53 protein in mouse skin. Bjelogrlic, NM; Mäkinen, M; Stenbäck, F; Vähäkangas, K, 1994)	0.29
" The number and size of arterial lesions in the brachiocephalic arteries in WC and SR females but not males were significantly enhanced after long-term dosing with BaP."	( Benzo(a)pyrene enhances atherosclerosis in White Carneau and Show Racer pigeons. Baird, MB; Darrow, D; Hough, JL; Pacini, CS; Sfeir, GT; Wheelock, C, 1993)	1.73
" Adduct analyses with varying amounts of DNA from lungs of mid- and high-exposure animals clearly indicate that the dose-response for DNA adduct formation is nonlinear."	( Ninety-day inhalation study in rats, using aged and diluted sidestream smoke from a reference cigarette: DNA adducts and alveolar macrophage cytogenetics. Brown, BG; Coggins, CR; Doolittle, DJ; Hayes, AW; Lee, CK; Reed, EA, 1993)	0.29
" No dose-response relationship was observed between the air benzo[alpha]pyrene concentrations and DNA adduct levels or percentage of detectable samples."	( DNA adducts as biomarkers for assessing exposure to polycyclic aromatic hydrocarbons in tissues from Xuan Wei women with high exposure to coal combustion emissions and high lung cancer mortality. Lee, X; Lewtas, J; Mumford, JL; Santella, RM; Young, TL, 1993)	0.29
" Therefore, a study was undertaken to determine in a dose-response manner the effect of AM phagocytosis of a carrier particle (Fe2O3) on the metabolism of a carcinogen (BaP) and on the production of reactive oxygen."	( Influence of the dose levels of cocarcinogen ferric oxide on the metabolism of benzo[a]pyrene by pulmonary alveolar macrophages in suspension culture. Greife, AL; Warshawsky, D, 1993)	0.29
" Dose-response studies were conducted at low doses in mouse skin by initiation-promotion and repeated application to compare its activity to that of 7,12-dimethylbenz[a]anthracene (DMBA), benzo[a]pyrene (B[a]P), DB[a,l]P-8,9-dihydrodiol and DB[a,l]P-11,12-dihydrodiol."	( Tumor-initiating activity and carcinogenicity of dibenzo[a,l]pyrene versus 7,12-dimethylbenz[a]anthracene and benzo[a]pyrene at low doses in mouse skin. Cavalieri, EL; Higginbotham, S; Johansson, SL; RamaKrishna, NV; Rogan, EG, 1993)	0.29
", 500, 250, and 50 micrograms/ml, in the presence of bioactivation, and at the highest dosage (500 micrograms/ml) in the absence of bioactivation."	( In vitro transforming effect of the fungicides metalaxyl and zineb. Bonora, B; Colacci, A; Grilli, S; Perocco, P, 1995)	0.29
" To verify this aspect further, the urinary excretion kinetic of 3-OHBaP following acute intraperitoneal dosing (31."	( Benzo(a)pyrenediolepoxide-hemoglobin adducts and 3-hydroxy-benzo(a)pyrene urinary excretion profiles in rats subchronically exposed to benzo(a)pyrene. Bouchard, M; Viau, C, 1995)	1.73
" This approach considers the mechanism of action of each compound and accounts for the fact that the extent of increase in toxic response caused by an incremental change of dose is determined by its position on the dose-response curve rather than on the absolute amount of dose administered."	( Immunosuppressive potential of several polycyclic aromatic hydrocarbons (PAHs) found at a Superfund site: new model used to evaluate additive interactions between benzo[a]pyrene and TCDD. Lipinskas, T; Silkworth, JB; Stoner, CR, 1995)	0.29
" The use of a combined PB/beta NF induction regime using oral dosing is therefore considered to be a suitable substitute for Aroclor 1254."	( Evaluation of phenobarbital/beta-naphthoflavone as an alternative S9-induction regime to Aroclor 1254 in the rat for use in in vitro genotoxicity assays. Callander, RD; Clay, P; Elcombe, CR; Elliott, BM; Mackay, JM, 1995)	0.29
" The animals were sacrificed at 6 hr, 24 hr, 48 hr, 7 days or 14 days after dosing to harvest skin specimens for the determination of radioactivity by autoradiographic and liquid scintillation methods, and to determine the dose that remained in the body."	( Skin reservoir formation and bioavailability of dermally administered chemicals in hairless guinea pigs. Bronaugh, R; Chu, I; Dick, D; Tryphonas, L, 1996)	0.29
" Slopes from the linear portions of the mutagenicity dose-response curves were analyzed by ANOVA comparisons."	( Effect of dietary casein levels on activation of promutagens in the spiral Salmonella mutagenicity assay. I. Studies with noninduced rat liver S9. Dauterman, WC; DeMarini, DM; Woodall, GM, 1996)	0.29
" Slopes from the linear portions of the mutagenicity dose-response curves were analyzed by ANOVA comparisons."	( Effect of dietary casein levels on activation of promutagens in the spiral Salmonella mutagenicity assay. II. Studies with induced rat liver S9. Dauterman, WC; DeMarini, DM; Woodall, GM, 1996)	0.29
" Adduct levels increased with increasing dose, but the slope of the dose-response was different in each organ."	( Chronic, topical exposure to benzo[a]pyrene induces relatively high steady-state levels of DNA adducts in target tissues and alters kinetics of adduct loss. Collins, T; Jaeger, M; Reilman, R; Talaska, G; Warshawsky, D, 1996)	0.29
" For both lung and stomach cancers, significant dose-response gradients were observed for exposure to total dust and benzo(a)pyrene, but not for specific chemical components of dust."	( Cancer risks among iron and steel workers in Anshan, China, Part II: Case-control studies of lung and stomach cancer. Blot, WJ; Brown, LM; Cao, RM; Dosemeci, M; Fraumeni, JF; Gao, GS; Guan, DX; Liu, TF; Pan, GW; Sheng, JH; Stone, BJ; Xu, Z; Yan, ZS, 1996)	0.5
" Toxicity constraints precluded administration of dosages high enough to induce statistically significant levels of terata in litters dosed with alpha-chaconine and permitted the attainment of only marginal statistical significance for alpha-solanine."	( Induction of terata in hamsters by solanidane alkaloids derived from Solanum tuberosum. Gaffield, W; Keeler, RF, 1996)	0.29
"The author discussed problems arising from the use of different mathematical dose-response models for extrapolation of cancer risk from high to low doses."	( [Methods of extrapolating risk from from high to low doses and their effect on determining MAC values]. Szymczak, W, 1996)	0.29
" Lutz, Dose-response relationship and low dose extrapolation in chemical carcinogenesis, Carcinogenesis, 11 (1990) 1243-1247) as a superlinear dose response."	( Air pollution exposure-DNA adduct dosimetry in humans and rodents: evidence for non-linearity at high doses. Dobiás, L; Lewtas, J; Walsh, D; Williams, R, 1997)	0.3
" Activation of PMN with PMA, or addition of more activated PMN in relation to the number of lung cells, further increased the number of adducts, the latter in a dose-response manner."	( Neutrophils amplify the formation of DNA adducts by benzo[a]pyrene in lung target cells. Borm, PJ; Godschalk, RW; Knaapen, AM; Schins, RP; Schooten, FJ, 1997)	0.3
"Groups of 4 male Wistar rats were dosed intravenously with 14C-labeled benzo[a]pyrene dissolved in an Emulphor/water vehicle at 3 different dose levels and killed at 1 of 15 specific time intervals from 5 min to 32 h after dosing."	( Pharmacokinetics of benzo[a]pyrene in the rat. Chu, I; McMullen, E; Moir, D; Viau, A; Withey, J, 1998)	0.3
" Conversely, more complex dose-response relationships were found by detecting in parallel the levels of an oxidative DNA lesion (8-OHdG) and of CYP1A-immunopositive proteins (the latter measured in the digestive gland only)."	( Tissue dose, DNA adducts, oxidative DNA damage and CYP1A-immunopositive proteins in mussels exposed to waterborne benzo[a]pyrene. Canova, S; Degan, P; Livingstone, DR; Peters, LD; Venier, P; Voltan, R, 1998)	0.3
" Dose-response curves for 1-NP and B[a]P were obtained; the number of net revertants/plate at the peak mutagenic dosage were 880 for 1-NP and 490 for B[a]P."	( Antimutagenic effects of natural phenolic compounds in beans. Castaño-Tostado, E; de Mejía, EG; Loarca-Piña, G, 1999)	0.3
" The dosage was 25 micromol/kg body weight of each substance, administered on 5 occasions with an interval of 12-14 days."	( DNA adduct formation and persistence in liver and extrahepatic tissues of northern pike (Esox lucius) following oral exposure to benzo[a]pyrene, benzo[k]fluoranthene and 7H-dibenzo[c,g]carbazole. Balk, L; Ericson, G; Noaksson, E, 1999)	0.3
" The in vivo dosing of flounder with benzo[a]pyrene (BaP) to produced DNA adducts in similar chromatographic positions to the diagonal radioactive zones in the Tyne caught flounder are also described."	( The detection of biomarkers of genotoxin exposure in the European flounder (Platichthys flesus) collected from the River Tyne Estuary. Kirby, MF; Lyons, BP; Stewart, C, 1999)	0.3
" A dose-response relationship was observed after exposing RTG-2 cells to vincristine sulfate and benzo(a)pyrene."	( Flow cytometric detection of micronuclei and cell cycle alterations in fish-derived cells after exposure to three model genotoxic agents: mitomycin C, vincristine sulfate and benzo(a)pyrene. Castaño, A; Llorente, MT; Sánchez, P, 2000)	0.72
" Primordial follicle destruction is known to result from dosing of mice and rats with three polycyclic aromatic hydrocarbons (PAHs), contaminants commonly found in cigarette smoke."	( Ovotoxicity in female Fischer rats and B6 mice induced by low-dose exposure to three polycyclic aromatic hydrocarbons: comparison through calculation of an ovotoxic index. Borman, SM; Christian, PJ; Hoyer, PB; Sipes, IG, 2000)	0.31
" Dose-response studies were carried out in mice for each chemical; each produced a unique pattern of gene induction."	( Applications of gene arrays in environmental toxicology: fingerprints of gene regulation associated with cadmium chloride, benzo(a)pyrene, and trichloroethylene. Bartosiewicz, M; Buckpitt, A; Penn, S, 2001)	0.52
" The extent of induced mutation was higher than that observed using rat embryo cells as the activating layer, although the shape of the dose-response curves was different."	( Metabolism of benzo[a]pyrene in human epidermal keratinocytes in culture. Kitano, Y; Kuroki, T; Nemoto, N, 1980)	0.26
"Dietary myo-inositol is an effective inhibitor of lung tumor induction in mice, but no dose-response studies have been reported."	( Dose-response study of myo-inositol as an inhibitor of lung tumorigenesis induced in A/J mice by benzo. Hecht, SS; Kenney, PM; Upadhyaya, P; Wang, M, 2001)	0.31
" A clear dose-response effect on formation of DNA adducts was obtained for B[a]P and a Standard Reference Material (SRM) of diesel particulate matter."	( Time- and dose-dependent DNA binding of PAHs derived from diesel particle extracts, benzo[a]pyrene and 5-methychrysene in a human mammary carcinoma cell line (MCF-7). Isotalo, S; Kuljukka-Rabb, T; Mikkonen, S; Peltonen, K; Rantanen, L; Savela, K, 2001)	0.31
"Bioavailability and toxicokinetic studies are essential in order to establish dose-response relationships of widely distributed environmental toxicants such as benzo[a]pyrene (BaP), a polycyclic aromatic hydrocarbon."	( Toxicokinetics of inhaled benzo[a]pyrene: plasma and lung bioavailability. Greenwood, M; Hood, DB; Inyang, F; Ramesh, A, 2001)	0.31
"2 mg/kg) dose of Cd, and in one treatment BP was dosed 4 days after Cd."	( Interactive effects of cadmium and benzo[a]pyrene on metallothionein induction in mummichog (Fundulus heteroclitus). Faisal, M; Roberts, MH; van den Hurk, P, )	0.13
" Neurotoxic effects peaked at 2 h after dosing and lasted 48 h after dosing for all dose groups."	( Modulation of neurotoxic behavior in F-344 rats by temporal disposition of benzo(a)pyrene. Ramesh, A; Saunders, CR; Shockley, DC, 2002)	0.54
" The dose-response relationship between biomarker and exposure dose was further incorporated into a dose-tumor response equation, obtained from 2-yr bioassay, to predict cancer risk."	( A proposed methodology of cancer risk assessment modeling using biomarkers. Kim, S; Lee, BM; Yoo, SD, 2002)	0.31
" Biological monitoring was performed through dosing of 1-hydroxypyrene (pyrene metabolite) in urine samples taken at the end of each workshift."	( Assessment of exposure to polycyclic aromatic hydrocarbons in police in Florence, Italy, through personal air sampling and biological monitoring of the urinary metabolite 1-hydroxypyrene. Bavazzano, P; Boddi, V; Gottardi, M; Lanciotti, E; Perico, A, )	0.13
"In order to study the effect of arsenic on DNA damage, Sprague-Dawley rats were dosed with sodium arsenite (10 mg/kg) with or without 800 microg of benzo(a)pyrene (BP) by intramammilary injection."	( Arsenic inhibits the repair of DNA damage induced by benzo(a)pyrene. Barnard, R; Chiswell, B; Ng, JC; Prakash, AS; Tran, HP, 2002)	0.76
" There was a significant correlation between deformity occurrence and EROD induction in embryos dosed with PCB alone but not for embryos dosed with BaP alone, or a combination of BaP and PCB 126."	( Effects of single and combined exposures to benzo(a)pyrene and 3,3'4,4'5-pentachlorobiphenyl on EROD activity and development in Fundulus heteroclitus. Di Giulio, RT; Swails, EE; Wassenberg, DM, )	0.39
" to study the dose-response relationship between B[a]P exposure and DNA adduct formation; and (c)."	( Tissue differences, dose-response relationship and persistence of DNA adducts in blue mussels (Mytilus edulis L) exposed to benzo[a]pyrene. Dalla Zuanna, L; Ericson, G; Gilek, M; Skarphéinsdóttir, H, 2003)	0.32
"0 mg [7,8-(3)H]benzo[a]pyrene (BP) were assayed by the same four assays and a dose-response was obtained with all assays."	( Highly sensitive chemiluminescence immunoassay for benzo[a]pyrene-DNA adducts: validation by comparison with other methods, and use in human biomonitoring. Beland, FA; Camara, JE; Divi, RL; Fu, PP; Ghei, M; Poirier, MC; Rothman, N; Schoket, B; Sinha, R; Von Tungeln, LS, 2002)	0.31
" The effects of BaP were estimated in terms of dose-response and time-response, with regard to the serum level of several APPs such as alpha-1-acid-glycoprotein (AAG), alpha-1-antitrypsin (AAT), C-reactive protein (CRP), and haptoglobin (HPT)."	( Acute-phase response to benzo[a]pyrene and induction of rat ALDH3A1. Karamanakos, P; Kostoula, A; Levidiotou, S; Marselos, M; Pappas, P; Sotiropoulou, M, 2003)	0.32
" to determine an EROD dose-response relationship of the contaminants used; and (3)."	( Induction of EROD activity in European eel (Anguilla anguilla) experimentally exposed to benzo[a]pyrene and beta-naphthoflavone. Bonacci, S; Chiea, R; Corsi, I; Focardi, S; Regoli, F, 2003)	0.32
" Inhibition of genotoxicity by spinach and peaches was not caused by any delay in maturation of micronucleated erythrocytes as shown by experiments with sampling times of 24, 48, and 72 h after dosing of BaP."	( Inhibition of clastogenicity of benzo[a]pyrene and of its trans-7,8-dihydrodiol in mice in vivo by fruits, vegetables, and flavonoids. Edenharder, R; Köttgen, V; Krieg, H; Platt, KL, 2003)	0.32
" 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)	0.52
" In this study, laparotomy on GD 8 was performed on timed-pregnant rats followed by dosing via nose-only exposure for 4h a day for 10 days (GD 11-GD 20) to three concentrations of a B(a)P: carbon black aerosol (25, 75 and 100 microg/m(3))."	( Assessment of metabolites and AhR and CYP1A1 mRNA expression subsequent to prenatal exposure to inhaled benzo(a)pyrene. Hood, DB; Nayyar, T; Ramesh, A; Wu, J, 2003)	0.53
"The three phosphorylated MAPKs expressional levels especially p-ERK1 had different extents of changes with dose-response relationship under BaP exposure."	( [Effects of mitogen activated protein kinase signal transduction pathways on heat shock protein 70 gene expression in endothelial cells exposed to benzo(a)pryene]. He, HZ; Hu, BC; Jiang, CZ; Ke, L; Wu, TC; Xu, Q; Yang, JB, 2004)	0.32
" At 3, 6, and 9 weeks, fish in each treatment group were dosed intraperitoneally with 10 mg tritiated benzo[a]pyrene [3H]-B[a]P/kg (B[a]P) to examine the effects of diet composition and energy intake on xenobiotic biotransformation and excretion."	( Influence of diet and ration level on benzo[a]pyrene metabolism and excretion in rainbow trout (Oncorhynchus mykiss). Higgs, D; Kennedy, CJ; Tierney, K, 2004)	0.32
" Fetal sensitivity and dose-response characteristics with regard to transplacental mutagenesis by these compounds have never been quantified."	( The mutagenic effects of 7,12-dimethylbenz[a]anthacene, 3-methylcholanthrene and benzo[a]pyrene to the developing Syrian hamster fetus measured by an in vivo/in vitro mutation assay. Donovan, PJ; Nardone, R; Smith, GT, 2004)	0.32
" Based in part on the emerging benchmark dose (BMD) method, the modified BMD method we used involves applying a suite of conventional mathematical models to tumor dose-response data."	( Application of benzo(a)pyrene and coal tar tumor dose-response data to a modified benchmark dose method of guideline development. Fitzgerald, DJ; Pester, BA; Robinson, NI, 2004)	0.68
"05), and indicated a dose-response relationship."	( Monitoring of pollution of air fine particles (PM2.5) and study on their genetic toxicity. Xu, DQ; Zhang, WL, 2004)	0.32
"01), and there was obvious dose-response relationship."	( [Effects of selenium on benzo[a] pyrene-induce DNA damage in mouse lung cells]. Chen, XM; Chen, XN; Li, XY; Lu, WQ; Mei, YH; Yu, RA; Zhu, JL, 2004)	0.32
" Bioaccumulation experiments were performed with Lumbriculus variegatus and Diporeia species exposed in seven sediments dosed with 2,4,5,2',4',5'-hexachlorobiphenyl (HCBP) and benzo[a]pyrene (BaP) or pyrene (PY) and 3,4,3',4'-tetrachlorobiphenyl (TCBP)."	( The contrasting roles of sedimentary plant-derived carbon and black carbon on sediment-spiked hydrophobic organic contaminant bioavailability to Diporeia species and Lumbriculus variegatus. Gossiaux, DC; Gunnarsson, J; Kukkonen, JV; Landrum, PF; Mitra, S; Weston, D, 2005)	0.33
" No significant dose-response relationship was found with the two compounds and no synergistic effect was observed between Fe3+ and B[a]P."	( DNA damage (comet assay) and 8-oxodGuo (HPLC-EC) in relation to oxidative stress in the freshwater bivalve Unio tumidus. Charissou, AM; Cossu-Leguille, C; Lemiere, S; Vasseur, P, )	0.13
" Many lines of convergent data obtained with oral benzo[a]pyrene dosing suggest that: 1) inducible CYP1A1, probably in both intestine and liver, is most important in detoxication; 2) CYP1B1 in spleen and marrow is responsible for metabolic activation of benzo[a]pyrene, which results in immune damage in the absence of CYP1A1; 3) both thymus atrophy and hepatocyte hypertrophy are independent of CYP1B1 metabolism but rather may reflect long-term activation of the aryl hydrocarbon receptor; and 4) the magnitude of immune damage in Cyp1a1-/- and Cyp1a1/1b1-/- mice is independent of plasma benzo[a]pyrene and total-body burden and clearance."	( Oral benzo[a]pyrene in Cyp1 knockout mouse lines: CYP1A1 important in detoxication, CYP1B1 metabolism required for immune damage independent of total-body burden and clearance rate. Curran, CP; Dalton, TP; Derkenne, S; Dragin, N; Gonzalez, FJ; Miller, ML; Nebert, DW; Shertzer, HG; Uno, S, 2006)	0.33
" In two separate experiments channel catfish (Ictalurus punctatus) were dosed with mixtures of benzo[a]pyrene with cadmium, chlorinated phenols or borneol."	( Bile fluorescence, heme oxygenase induction, and increased biliverdin excretion by mixtures of environmental toxicants. van den Hurk, P, 2006)	0.33
" Embryos incubated directly on sediments dosed with the reference mutagen, benzo[alpha]pyrene (BaP), were examined for BaP uptake and metabolism."	( Uptake, metabolism, mutant frequencies and mutational spectra in lambda transgenic medaka embryos exposed to benzo[alpha]pyrene dosed sediments. Bogler, A; McElroy, AE; Mendelman, LV; Norris, M; Setlow, R; Weisbaum, D; Winn, R, 2006)	0.33
" Channel catfish (Ictalurus punctatus) were dosed with mixtures of benzo[a]pyrene and cadmium, chlorinated phenols or borneol."	( Heme oxygenase induction and biliverdin excretion: implications for the bile fluorescence biomarker. van den Hurk, P, 2006)	0.33
" Calf thymus DNA reacted with B[a]PDE in vitro and mouse liver DNA samples at different time points following dosing intraperitoneally with 50, 100, and 200 mg/kg B[a]P was analyzed."	( Detection and quantitation of benzo[a]pyrene-derived DNA adducts in mouse liver by liquid chromatography-tandem mass spectrometry: comparison with 32P-postlabeling. Azim-Araghi, A; Farmer, PB; Gaskell, M; Kaur, B; Koukouves, G; Kyrtopoulos, SA; Le Pla, RC; Roach, J; Singh, R; Souliotis, VL, 2006)	0.33
" Dose-response and time-course studies indicated that mutagenicity was reduced up to 3-fold by hGSTP1 expression, compared with cells expressing hCYP1A1 alone."	( Expression of human glutathione S-transferase P1 confers resistance to benzo[a]pyrene or benzo[a]pyrene-7,8-dihydrodiol mutagenesis, macromolecular alkylation and formation of stable N2-Gua-BPDE adducts in stably transfected V79MZ cells co-expressing hCYP Doehmer, J; Fleming, MH; Gupta, RC; Kabler, SL; Kushman, ME; Morrow, CS; Ravoori, S; Townsend, AJ, 2007)	0.34
" A dose-response relationship was demonstrated between intestinal EROD activities and the levels of foodborne BaP."	( Temporal changes of ethoxyresorufin-o-deethylase (EROD) activities and lysosome accumulation in intestine of fish on chronic exposure to dietary benzo[a]pyrene: linking erod induction to cytological effects. Au, DW; Yuen, BB, 2006)	0.33
"To compare the dose-response relationships for two common measures of coal tar-derived substances, benzene-soluble material (BSM) and benzo(a)pyrene (BaP), and to evaluate which among these is more strongly related to the health outcomes."	( Comparison of two indices of exposure to polycyclic aromatic hydrocarbons in a retrospective aluminium smelter cohort. Demers, PA; Friesen, MC; Le, ND; Lorenzi, MF; Spinelli, JJ, 2007)	0.54
" The shape, magnitude and precision of the dose-response relationships and cumulative exposure levels for BSM and BaP were evaluated."	( Comparison of two indices of exposure to polycyclic aromatic hydrocarbons in a retrospective aluminium smelter cohort. Demers, PA; Friesen, MC; Le, ND; Lorenzi, MF; Spinelli, JJ, 2007)	0.34
" The log-log dose-response models, where risk of disease plateaus at high exposure levels, were the best-fitting models for lung cancer and AMI."	( Comparison of two indices of exposure to polycyclic aromatic hydrocarbons in a retrospective aluminium smelter cohort. Demers, PA; Friesen, MC; Le, ND; Lorenzi, MF; Spinelli, JJ, 2007)	0.34
" Both S-29606 and S-30621 were dosed via nose-only inhalation 5 days a week, for 16 weeks, whereas Zileuton was administered orally."	( Effects of novel 5-lipoxygenase inhibitors on the incidence of pulmonary adenomas in the A/J murine model when administered via nose-only inhalation. Angersbach, BS; Karlage, K; Kuehl, PJ; Merrill, BA; Myrdal, PB; Wightman, PD, 2007)	0.34
" Lung tumor yield was examined on the 84th day and 140 days after B(a)P dosing and 240 days after NTCU treatment."	( Oral consumption of pomegranate fruit extract inhibits growth and progression of primary lung tumors in mice. Afaq, F; Khan, N; Kim, K; Kweon, MH; Mukhtar, H, 2007)	0.34
" Dose-response curves for growth inhibition were determined and four concentrations eliciting from "no effect" up to a severe growth inhibition were chosen for further investigation to detect alterations at gene expression level by Real-Time PCR."	( Gene regulation in the marine diatom Thalassiosira pseudonana upon exposure to polycyclic aromatic hydrocarbons (PAHs). Bopp, SK; Lettieri, T, 2007)	0.34
" The results indicated that significant dose-response relationship was observed between ABA contents and the concentrations of single fluoranthene and combined pollution of fluoranthene and benzo(a)pyrene, and ABA content responded more intensive to single fluoranthene than to combined treatment."	( [Dose-response relationships between endogenous phytohormones of high plant and concentrations of fluoranthene and benzo(a)pyrene in soils]. Li, XY; Song, YF; Sun, TH; Zhou, QX, 2007)	0.74
" To further investigate reciprocal effects of different chemicals, the fish Trematomus bernacchii was exposed to trace metals (Cd, Cu, Hg, Ni, Pb) and benzo[a]pyrene (BaP, as a model PAH), dosed alone and in combinations."	( Oxidative and modulatory effects of trace metals on metabolism of polycyclic aromatic hydrocarbons in the Antarctic fish Trematomus bernacchii. Barucca, M; Benedetti, M; Canapa, A; Fattorini, D; Martuccio, G; Nigro, M; Regoli, F, 2007)	0.34
" However, no laboratory dose-response and/or time course studies related to applied biomarkers have been reported on chub yet."	( Hepatic biomarker responses to organic contaminants in feral chub (Leuciscus cephalus)--laboratory characterization and field study in the Sava River, Croatia. Ahel, M; Calić, V; Grubesić, MS; Krca, S; Smital, T; Terzić, S; Zaja, R, 2007)	0.34
" In this study, we investigated the effect of two dosing regimens on the mutagenicity of DB[a,l]P and B[a]P in vivo using the Big Blue(R) transgenic mouse system."	( Mutations induced by benzo[a]pyrene and dibenzo[a,l]pyrene in lacI transgenic B6C3F1 mouse lung result from stable DNA adducts. George, MH; Leavitt, SA; Moore, T; Ross, JA, 2008)	0.35
" The dose-response curve of B(a)P was linear for Olive TM, but sigmoid for CBMN frequency."	( [Different change of olive tail moment and cytokinesis-block micronucleus frequency of the cells of 4 kinds treated with polycyclic aromatic hydrocarbon]. Cheng, J; Duan, H; Leng, S; Niu, Y, 2008)	0.35
" To validate this method in killifish, DNA damage was measured in liver, brain, and muscle of fish dosed with 10 mg/kg benzo[a]pyrene."	( The long amplicon quantitative PCR for DNA damage assay as a sensitive method of assessing DNA damage in the environmental model, Atlantic killifish (Fundulus heteroclitus). Cho, Y; Di Giulio, RT; Jung, D; Meyer, JN, 2009)	0.35
" Induction of intestinal metallothionein mRNA was apparent, however, and a linear dose-response relationship was observed for metallothionein expression and cadmium dose in the intestine, but not the other organs, which showed no induction."	( Dietary cadmium and benzo(a)pyrene increased intestinal metallothionein expression in the fish Fundulus heteroclitus. Mitelberg, A; Perez-Matus, A; Rezvankhah, S; Roesijadi, G; Torruellas, K; Van Veld, PA, 2009)	0.68
" Embryos were dosed from 24 to 120 h post-fertilization (hpf) and were analyzed for induction of CYP1 enzymatic activity as measured by the ethoxyresorufin-O-deethylase (EROD) assay, cardiac deformities, and BaP metabolic profile."	( Effect of CYP1A inhibition on the biotransformation of benzo[a]pyrene in two populations of Fundulus heteroclitus with different exposure histories. Di Giulio, RT; Willett, KL; Wills, LP; Zhu, S, 2009)	0.35
"8 microg/g dry weight of BaP, and exhibited a dose-response relationship in fish exposed to SN diets."	( A fish bioassay to evaluate the toxicity associated with the ingestion of benzo[a]pyrene-contaminated benthic prey. Couillard, CM; Laplatte, B; Pelletier, E, 2009)	0.35
" A dosage up to 10 microg/ml of AN was devoid of mutagenic activity."	( Effect of annatto on micronuclei induction by direct and indirect mutagens in HepG2 cells. Angeli, JP; Antunes, LM; Barcelos, GR; Mantovani, MS; Rocha, BA; Serpeloni, JM, 2009)	0.35
" Thus, ACB-PCR may be useful in characterizing the shape of a dose-response curve at low doses and establishing relationships between DNA adducts and tumor-associated mutations."	( K-Ras mutant fraction in A/J mouse lung increases as a function of benzo[a]pyrene dose. Green, T; Knapp, GW; Meng, F; Parsons, BL; Ross, JA, 2010)	0.36
" Here, we examined mtDNA and nDNA damage in the Atlantic killifish (Fundulus heteroclitus) from a highly contaminated Superfund site (Elizabeth River, VA, USA) and from a reference site (King's Creek, VA, USA) that were dosed with 10 mg/kg BaP."	( Effects of benzo[a]pyrene on mitochondrial and nuclear DNA damage in Atlantic killifish (Fundulus heteroclitus) from a creosote-contaminated and reference site. Cho, Y; Collins, LB; Di Giulio, RT; Jung, D; Swenberg, JA, 2009)	0.35
" Fish dosed with 10mg/kg BaP had increased EROD activity in the mitochondrial fraction compared to controls."	( Identification of mitochondrial cytochrome P450 induced in response to polycyclic aromatic hydrocarbons in the mummichog (Fundulus heteroclitus). Di Giulio, RT; Jung, D, 2010)	0.36
" Carcinogenicity studies of coal tar mixtures, considered to be representative of the genotoxic and carcinogenic PAH in food, have been used for dose-response modelling."	( Application of the margin-of-exposure (MoE) approach to substances in food that are genotoxic and carcinogenic e.g.: benzo[a]pyrene and polycyclic aromatic hydrocarbons. Benford, D; Dinovi, M; Setzer, RW, 2010)	0.36
" Following high dosage of oral BaP (125 mg/kg/day), ablation of the mouse Cyp1a1 gene causes immunosuppression and death within ∼28 days, whereas Cyp1(+/+) wild-type mice remain healthy for >12 months on this regimen."	( Oral benzo[a]pyrene-induced cancer: two distinct types in different target organs depend on the mouse Cyp1 genotype. Chen, J; Dragin, N; Gonzalez, FJ; Johansson, E; Miller, ML; Nebert, DW; Rubio, CA; Shi, Z; Stringer, KF; Uno, S, 2010)	0.36
" Additional groups of mice were dosed once with BPQ or BP-7,8-diol each at 30 mg/kg and tissues harvested 48 and 72 h later, or with B[a]P (50mg/kg, a tumorigenic dose) and tissues harvested 72 h later."	( Lack of contribution of covalent benzo[a]pyrene-7,8-quinone-DNA adducts in benzo[a]pyrene-induced mouse lung tumorigenesis. Adams, LD; George, MH; King, LC; Moore, T; Nelson, G; Nesnow, S; Padgett, WT; Ross, JA, 2010)	0.36
"The apoptotic rate of neuron increased in both the middle dose group and the high dose group compared with controls, and had a dose-response tendency with the concentration of B(a)P."	( [Changes of mitochondria membrane potential and cytoplasmic cytochrome C in neuron apoptosis induced by benzo(a)pyrene]. Liu, HJ; Nie, JS; Niu, Q; Zhang, HM; Zhang, QL; Zhao, J, 2010)	0.58
" However, dose-response relationship differed between these two PAHs with a concentration-dependent inhibition of BPDE-N²-dGuo DNA by B[k]F whereas a constant level of potentiation for B[b]F was observed for concentrations higher than 1 μM."	( Polycyclic aromatic hydrocarbons in binary mixtures modulate the efficiency of benzo[a]pyrene to form DNA adducts in human cells. Douki, T; Lefèbvre, E; Maître, A; Marques, M; Rajhi, A; Tarantini, A, 2011)	0.37
" The aim of this study was to develop a partition-controlled dosing system to maintain constant concentrations of benzo(a)pyrene, 1,2-dichlorobenzene, and 1,2,4-trichlorobenzene in an ethoxyresorufin-O-deethylase (EROD) assay and a cytotoxicity assay with the rainbow trout (Oncorhynchus mykiss) cell lines RTL-W1 and RTgill-W1."	( Development of a partition-controlled dosing system for cell assays. Busser, FJ; Escher, BI; Hermens, JL; Kramer, NI; Oosterwijk, MT; Schirmer, K, 2010)	0.57
" Induction kinetics were calculated using a logistic-like model and approximate dose-response curves were designed."	( EROD activity in peripheral blood lymphocytes and 1-hydroxypyrene in urine and milk as biomarkers of PAH exposure in dairy ruminants. Chahin, A; Dziurla, MA; Guiavarc'h, YP; Jondreville, C; Rychen, G; Yen, FT, 2011)	0.37
" We investigated the pattern of dose-response in mammalian cells to various environmental contaminants using a range of concentrations that span those that are environmentally relevant (10(-12)M to 10(-3)M)."	( Derivation by infrared spectroscopy with multivariate analysis of bimodal contaminant-induced dose-response effects in MCF-7 cells. Jones, KC; Llabjani, V; Martin, FL; Shore, RF; Trevisan, J, 2011)	0.37
"5 and 5 micromol/L), observing dose-response relationship and time-dependent relationship, respectively."	( [Effect of benzo [a] pyrene on HSP70 expression in rat cortical neurons in vitro]. Xu, G; Zheng, J, 2011)	0.37
" Muta™Mouse were dosed daily for 28 days with benzo[a]pyrene (BaP; 0, 25, 50 and 75 mg/kg body weight/day) by oral gavage."	( Simultaneous measurement of benzo[a]pyrene-induced Pig-a and lacZ mutations, micronuclei and DNA adducts in Muta™ Mouse. Arlt, VM; Dertinger, SD; Douglas, GR; Gingerich, J; Lemieux, CL; Phillips, DH; Phonethepswath, S; Torous, DK; White, PA, 2011)	0.37
" The dosing time-dependency of benzo[α]pyrene-induced Cyp1a1 expression was also modulated by Clock gene mutation."	( Aryl hydrocarbon receptor-mediated Cyp1a1 expression is modulated in a CLOCK-dependent circadian manner. Koyanagi, S; Kusunose, N; Matsunaga, N; Ohdo, S; Tanimura, N, 2011)	0.37
" A dose-response increase in the expression of hsp70 and IL-1β mRNA was found."	( Gene expression of heat shock protein 70, interleukin-1β and tumor necrosis factor α as tools to identify immunotoxic effects on Xenopus laevis: a dose-response study with benzo[a]pyrene and its degradation products. Fernández, C; Martini, F; Pablos, MV; Tarazona, JV, 2012)	0.38
" A dose-response of BaP on diatoms has been made and the effect of this compound on the expression of selected genes was assessed by quantitative real time-PCR."	( Transcriptomics responses in marine diatom Thalassiosira pseudonana exposed to the polycyclic aromatic hydrocarbon benzo[a]pyrene. Bopp, SK; Carvalho, RN; Lettieri, T, 2011)	0.37
" In general, there was increased damage in the spermatozoa by comparison with the lymphocytes, with altered slopes in the dose-response curves."	( Comet-assay parameters as rapid biomarkers of exposure to dietary/environmental compounds -- an in vitro feasibility study on spermatozoa and lymphocytes. Anderson, D; Baumgartner, A; Cemeli, E; Kurzawa-Zegota, M; Laubenthal, J, 2012)	0.38
" The shape of bacterial population (logarithm of colony-forming unit) dose-response curve generally matched those of biliary FACs concentrations."	( Use of intestinal Pseudomonas aeruginosa in fish to detect the environmental pollutant benzo[a]pyrene. Christianus, A; Courtenay, SC; Ishak, Z; Karami, A; Masoumian, M; Shamsuddin, ZH, 2012)	0.38
" The results of these studies indicate that cigarette smoking, coffee drinking, and the ingestion of charcoal-broiled beef (all resulting in exposure to polycyclic aromatic hydrocarbons) can influence the dosing regimen needed for proper drug therapy and are potential confounders of clinical trials with drugs metabolized by polycyclic aromatic hydrocarbon-inducible enzymes."	( Cigarette smoking, coffee drinking, and ingestion of charcoal-broiled beef as potential modifiers of drug therapy and confounders of clinical trials. Conney, AH; Reidenberg, MM, 2012)	0.38
" The ability to effectively monitor these endpoints in short-term and repeated dosing schedules was investigated with the carcinogen/noncarcinogen pair benzo(a)pyrene (BP) and pyrene (Pyr)."	( In vivo flow cytometric Pig-a and micronucleus assays: highly sensitive discrimination of the carcinogen/noncarcinogen pair benzo(a)pyrene and pyrene using acute and repeated-dose designs. Avlasevich, SL; Bell, S; Bemis, JC; Bryce, SM; Custer, LL; Dertinger, SD; Gleason, C; MacGregor, JT; Mereness, J; Phonethepswath, S; Torous, DK; Weller, P, 2012)	0.78
"This study represents a first attempt at applying a fuzzy inference system (FIS) and an adaptive neuro-fuzzy inference system (ANFIS) to the field of aquatic biomonitoring for classification of the dosage and time of benzo[a]pyrene (BaP) injection through selected biomarkers in African catfish (Clarias gariepinus)."	( Fuzzy logic and adaptive neuro-fuzzy inference system for characterization of contaminant exposure through selected biomarkers in African catfish. Courtenay, SC; Hollert, H; Karami, A; Keiter, S, 2013)	0.39
" This was done to evaluate potential degradation and thereby biological conversion of the cyclodextrins if dosed orally, as the intestinal tract contains α-amylase for digestive purposes."	( In vitro investigations of α-amylase mediated hydrolysis of cyclodextrins in the presence of ibuprofen, flurbiprofen, or benzo[a]pyrene. Holm, R; Jørgensen, EB; Larsen, KL; Lumholdt, LR, 2012)	0.38
"The use of sensitive test systems makes it possible to detect weakly genotoxic chemicals and to better define the shape of dose-response relationships, which make it easier to interpret the mechanism behind possible effects."	( The use of immunomagnetic separation of erythrocytes in the in vivo flow cytometer-based micronucleus assay. Abramsson-Zetterberg, L; Carlsson, R; Sand, S, 2013)	0.39
"Although pulmonary dosing of large porous particles has been shown to sustain drug delivery for a few days, there are no reports on safety or long term delivery."	( Supercritical fluid technology based large porous celecoxib-PLGA microparticles do not induce pulmonary fibrosis and sustain drug delivery and efficacy for several weeks following a single dose. Dhanda, DS; Kompella, UB; Mirvish, SS; Tyagi, P, 2013)	0.39
"We reviewed the literature on health effects, community exposure data, and dose-response relationships of the principal hazardous agents emitted."	( Community health risk assessment of primary aluminum smelter emissions. Larivière, C; Martin, SC, 2014)	0.4
" The present study compares thin-film and solvent-delivery dosing techniques as well as single versus multiple chemical dosing for measuring biotransformation rates of selected polycyclic aromatic hydrocarbons in rainbow trout (Oncorhynchus mykiss) liver S9."	( In vitro biotransformation rates in fish liver S9: effect of dosing techniques. Delafoulhouze, M; Gobas, FA; Kennedy, CJ; Lee, DH; Lee, YS; Moore, MM; Otton, SV, 2014)	0.4
" In this study we evaluate whether interindividual variation in baseline enzyme activity (EA)/gene expression (GE) levels in liver predispose for the variation in toxicity responses by assessing dose-response relationships for several prototypical hepatotoxicants."	( Interindividual variation in response to xenobiotic exposure established in precision-cut human liver slices. Castell, JV; Claessen, SM; Dejong, CH; Jetten, MJ; Kleinjans, JC; Lahoz, A; van Delft, JH, 2014)	0.4
" We found that toxicogenomics provided rich mechanistic data applicable to hazard identification, dose-response analysis, and quantitative RA of BaP."	( Integrating toxicogenomics into human health risk assessment: lessons learned from the benzo[a]pyrene case study. Bourdon-Lacombe, J; Buick, JK; Chepelev, NL; Halappanavar, S; Kuo, B; Labib, S; Lemieux, F; Malik, AI; Moffat, ID; Williams, A; Yauk, CL, 2015)	0.42
" carpio showed the highest CYP1A induction level and the steepest slope in the dose-response curve."	( Benzo(a)pyrene-induced cytochrome p4501A expression of four freshwater fishes (Oryzias latipes, Danio rerio, Cyprinus carpio, and Zacco platypus). Lee, JW; Lee, SK; Yoon, HG, 2015)	1.86
" Depletion rate constants measured using thin-film sorbent dosing experiments were not statistically different from the maximum depletion rate constants derived using a series of solvent delivery-based depletion experiments for 3 of the 4 test chemicals."	( Concentration dependence of biotransformation in fish liver S9: Optimizing substrate concentrations to estimate hepatic clearance for bioaccumulation assessment. Allard, GN; Campbell, DA; Gobas, FA; Lo, JC; Otton, SV, 2015)	0.42
" We first assessed the effects of BaP (150 and 300 µg kg(-1) body weight) dosed via gavage from day 14 to 17 of pregnancy on gestation length in Long Evans rats."	( Altered expression of histone deacetylases, inflammatory cytokines and contractile-associated factors in uterine myometrium of Long Evans rats gestationally exposed to benzo[a]pyrene. Al-Hendy, A; Bobb, LE; Foster, TL; Hood, DB; Ladson, GM; Laknaur, A; Ramesh, A; Thota, C, 2016)	0.43
" Both cyclodextrins lowered the area under the curve and therefore the absorption of benzo[a]pyrene by up to a factor of 2 when dosed in high concentrations, thus indicating that overdosing of cyclodextrins may limit the oral absorption of a compound."	( Does the Digestibility of Cyclodextrins Influence the In Vivo Absorption of Benzo[a]pyrene in Rats? Holm, R; Olesen, NE; Vana, V, 2016)	0.43
" The colon tumor numbers showed a B(a)P dose-response relationship."	( Western diet enhances benzo(a)pyrene-induced colon tumorigenesis in a polyposis in rat coli (PIRC) rat model of colon cancer. Adunyah, SE; Amos-Landgraf, JM; Guo, Z; Harris, KL; Okoro, E; Pulliam, SR; Ramesh, A; Washington, MK, 2016)	0.75
" Dose-response modelling suggested that the mutational response in male germ cells to BaP is sub-linear at low doses."	( Benzo(a)pyrene Is Mutagenic in Mouse Spermatogonial Stem Cells and Dividing Spermatogonia. Beal, MA; Marchetti, F; O'Brien, JM; Yauk, CL, 2016)	1.88
"Twelve spiked soil samples and a spiked silica sand (reference material) were dosed to rats in parallel with a swine study."	( Comparison of oral bioavailability of benzo[a]pyrene in soils using rat and swine and the implications for human health risk assessment. Dong, Z; Duan, L; Herde, P; Kuchel, T; Liu, Y; Mallavarapu, M; Naidu, R; Semple, KT, 2016)	0.43
"Both AUC and faecal excretion assays showed linear dose-response for the reference material."	( Comparison of oral bioavailability of benzo[a]pyrene in soils using rat and swine and the implications for human health risk assessment. Dong, Z; Duan, L; Herde, P; Kuchel, T; Liu, Y; Mallavarapu, M; Naidu, R; Semple, KT, 2016)	0.43
" BaP-induced Cyp1a1 and Cyp1b1 mRNA levels were higher 4 hours after dosing at noon than at 4 hours after dosing at midnight, and this corresponded with parallel changes in Per gene expression."	( Circadian Regulation of Benzo[a]Pyrene Metabolism and DNA Adduct Formation in Breast Cells and the Mouse Mammary Gland. Barhoumi, R; Metz, RP; Porter, WW; Schmitt, EE, 2017)	0.46
" We also dosed with benzo[k]fluoranthene (BkF) and showed significant induction of CYP1A activity, with no concurrent increase in CYP3A activity."	( A non-destructive BFCOD assay for in vivo measurement of cytochrome P450 3A (CYP3A) enzyme activity in fish embryos and larvae. Carey, AN; Matson, CW; Oziolor, EM, 2017)	0.46
" Based on dose-response of γH2AX and Hill model, the ability to induce DSBs was evaluated: NNN-acetate > B[a]P > NNK-acetate > tar > nicotine."	( Genotoxicity analysis of five particle matter toxicants from cigarette smoke based on γH2AX assay combined with Hill/Two-component model. Chen, H; Hou, H; Hu, Q; Liu, Y; Wang, A; Zhang, S, 2018)	0.48
" The dosage of the dermal and oral ingestion entry routes of PAHs was determined."	( Groundwater contamination by polycyclic aromatic hydrocarbon due to diesel spill from a telecom base station in a Nigerian City: assessment of human health risk exposure. Ochonogor, A; Ugochukwu, UC, 2018)	0.48
" 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
" In addition, FLT1 hypermethylation and gene suppression appeared in primary human lymphocytes in a dose-response manner following COEs treatment."	( FLT1 hypermethylation is involved in polycyclic aromatic hydrocarbons-induced cell transformation. Chen, L; Chen, S; Chen, W; Dong, G; Duan, H; He, Z; Li, D; Li, H; Li, Q; Niu, Y; Wang, Q; Wang, Z; Xiao, Y; Xing, X; Ye, L; Yu, D; Zhang, R; Zheng, Y, 2019)	0.51
" Passive dosing promises to have an advantage over traditional 'solvent spiking' exposure methods and involves the establishment and maintenance of known chemical concentrations in the in vitro medium, and therefore aqueous phase."	( Comparison of passive-dosed and solvent spiked exposures of pro-carcinogen, benzo[a]pyrene, to human lymphoblastoid cell line, MCL-5. Chapman, FM; Chapman, KE; Doak, SH; Hastie, C; Jenkins, GJS; Sanders, DJ; Scott, AD; Sparham, C; van Egmond, R, 2020)	0.56
"Findings will provide timely information on the safety, efficacy, and optimal dosing of t-PA to treat moderate/severe COVID-19-induced ARDS, which can be rapidly adapted to a phase III trial (NCT04357730; FDA IND 149634)."	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Beckers, C; Bedel, J; Bedlack, R; Bermúdez de Castro, JM; Berry, JD; Berthier, C; Bhattacharya, D; Biadgo, B; Bianco, G; Bianco, M; Bibi, S; Bigliardi, AP; Billheimer, D; Birnie, DH; Biswas, K; Blair, HC; Bognetti, P; Bolan, PJ; Bolla, JR; Bolze, A; Bonnaillie, P; Borlimi, R; Bórquez, J; Bottari, NB; Boulleys-Nana, JR; Brighetti, G; Brodeur, GM; Budnyak, T; Budnyk, S; Bukirwa, VD; Bulman, DM; Burm, R; Busman-Sahay, K; Butcher, TW; Cai, C; Cai, H; Cai, L; Cairati, M; Calvano, CD; Camacho-Ordóñez, A; Camela, E; Cameron, T; Campbell, BS; Cansian, RL; Cao, Y; Caporale, AS; Carciofi, AC; Cardozo, V; Carè, J; Carlos, AF; Carozza, R; Carroll, CJW; Carsetti, A; Carubelli, V; Casarotta, E; Casas, M; Caselli, G; Castillo-Lora, J; Cataldi, TRI; Cavalcante, ELB; Cavaleiro, A; Cayci, Z; Cebrián-Tarancón, C; Cedrone, E; Cella, D; Cereda, C; Ceretti, A; Ceroni, M; Cha, YH; Chai, X; Chang, EF; Chang, TS; Chanteux, H; Chao, M; Chaplin, BP; Chaturvedi, S; Chaturvedi, V; Chaudhary, DK; Chen, A; Chen, C; 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Douglas, RG; Duarte, PF; Dullaart, RPF; Duscha, BD; Edwards, LA; Edwards, TE; Eichenwald, EC; El-Baba, TJ; Elashiry, M; Elashiry, MM; Elashry, SH; Elliott, A; Elsayed, R; Emerson, MS; Emmanuel, YO; Emory, TH; Endale-Mangamba, LM; Enten, GA; Estefanía-Fernández, K; Estes, JD; Estrada-Mena, FJ; Evans, S; Ezra, L; Faria de, RO; Farraj, AK; Favre, C; Feng, B; Feng, J; Feng, L; Feng, W; Feng, X; Feng, Z; Fernandes, CLF; Fernández-Cuadros, ME; Fernie, AR; Ferrari, D; Florindo, PR; Fong, PC; Fontes, EPB; Fontinha, D; Fornari, VJ; Fox, NP; Fu, Q; Fujitaka, Y; Fukuhara, K; Fumeaux, T; Fuqua, C; Fustinoni, S; Gabbanelli, V; Gaikwad, S; Gall, ET; Galli, A; Gancedo, MA; Gandhi, MM; Gao, D; Gao, K; Gao, M; Gao, Q; Gao, X; Gao, Y; Gaponenko, V; Garber, A; Garcia, EM; García-Campos, C; García-Donas, J; García-Pérez, AL; Gasparri, F; Ge, C; Ge, D; Ge, JB; Ge, X; George, I; George, LA; Germani, G; Ghassemi Tabrizi, S; Gibon, Y; Gillent, E; Gillies, RS; Gilmour, MI; Goble, S; Goh, JC; Goiri, F; Goldfinger, LE; Golian, M; Gómez, MA; Gonçalves, J; Góngora-García, OR; Gonul, I; González, MA; Govers, TM; Grant, PC; Gray, EH; Gray, JE; Green, MS; Greenwald, I; Gregory, MJ; Gretzke, D; Griffin-Nolan, RJ; Griffith, DC; Gruppen, EG; Guaita, A; Guan, P; Guan, X; Guerci, P; Guerrero, DT; Guo, M; Guo, P; Guo, R; Guo, X; Gupta, J; Guz, G; Hajizadeh, N; Hamada, H; Haman-Wabi, AB; Han, TT; Hannan, N; Hao, S; Harjola, VP; Harmon, M; Hartmann, MSM; Hartwig, JF; Hasani, M; Hawthorne, WJ; Haykal-Coates, N; Hazari, MS; He, DL; He, P; He, SG; Héau, C; Hebbar Kannur, K; Helvaci, O; Heuberger, DM; Hidalgo, F; Hilty, MP; Hirata, K; Hirsch, A; Hoffman, AM; Hoffmann, JF; Holloway, RW; Holmes, RK; Hong, S; Hongisto, M; Hopf, NB; Hörlein, R; Hoshino, N; Hou, Y; Hoven, NF; Hsieh, YY; Hsu, CT; Hu, CW; Hu, JH; Hu, MY; Hu, Y; Hu, Z; Huang, C; Huang, D; Huang, DQ; Huang, L; Huang, Q; Huang, R; Huang, S; Huang, SC; Huang, W; Huang, Y; Huffman, KM; Hung, CH; Hung, CT; Huurman, R; Hwang, SM; Hyun, S; Ibrahim, AM; Iddi-Faical, A; 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Laloo, A; Langaro, MC; Langham, MC; Lao, X; Larocca, MC; Lassus, J; Lattimer, TA; Lazar, S; Le, MH; Leal, DB; Leal, M; Leary, A; Ledermann, JA; Lee, JF; Lee, MV; Lee, NH; Leeds, CM; Leeds, JS; Lefrandt, JD; Leicht, AS; Leonard, M; Lev, S; Levy, K; Li, B; Li, C; Li, CM; Li, DH; Li, H; Li, J; Li, L; Li, LJ; Li, N; Li, P; Li, T; Li, X; Li, XH; Li, XQ; Li, XX; Li, Y; Li, Z; Li, ZY; Liao, YF; Lin, CC; Lin, MH; Lin, Y; Ling, Y; Links, TP; Lira-Romero, E; Liu, C; Liu, D; Liu, H; Liu, J; Liu, L; Liu, LP; Liu, M; Liu, T; Liu, W; Liu, X; Liu, XH; Liu, Y; Liuwantara, D; Ljumanovic, N; Lobo, L; Lokhande, K; Lopes, A; Lopes, RMRM; López-Gutiérrez, JC; López-Muñoz, MJ; López-Santamaría, M; Lorenzo, C; Lorusso, D; Losito, I; Lu, C; Lu, H; Lu, HZ; Lu, SH; Lu, SN; Lu, Y; Lu, ZY; Luboga, F; Luo, JJ; Luo, KL; Luo, Y; Lutomski, CA; Lv, W; M Piedade, MF; Ma, J; Ma, JQ; Ma, JX; Ma, N; Ma, P; Ma, S; Maciel, M; Madureira, M; Maganaris, C; Maginn, EJ; Mahnashi, MH; Maierhofer, M; Majetschak, M; Malla, TR; Maloney, L; Mann, DL; Mansuri, A; Marelli, E; Margulis, CJ; Marrella, A; Martin, BL; Martín-Francés, L; Martínez de Pinillos, M; Martínez-Navarro, EM; Martinez-Quintanilla Jimenez, D; Martínez-Velasco, A; Martínez-Villaseñor, L; Martinón-Torres, M; Martins, BA; Massongo, M; Mathew, AP; Mathews, D; Matsui, J; Matsumoto, KI; Mau, T; Maves, RC; Mayclin, SJ; Mayer, JM; Maynard, ND; Mayr, T; Mboowa, MG; McEvoy, MP; McIntyre, RC; McKay, JA; McPhail, MJW; McVeigh, AL; Mebazaa, A; Medici, V; Medina, DN; Mehmood, T; Mei-Li, C; Melku, M; Meloncelli, S; Mendes, GC; Mendoza-Velásquez, C; Mercadante, R; Mercado, MI; Merenda, MEZ; Meunier, J; Mi, SL; Michels, M; Mijatovic, V; Mikhailov, V; Milheiro, SA; Miller, DC; Ming, F; Mitsuishi, M; Miyashita, T; Mo, J; Mo, S; Modesto-Mata, M; Moeller, S; Monte, A; Monteiro, L; Montomoli, J; Moore, EE; Moore, HB; Moore, PK; Mor, MK; Moratalla-López, N; Moratilla Lapeña, L; Moreira, R; Moreno, MA; Mörk, AC; Morton, M; Mosier, JM; Mou, LH; Mougharbel, AS; Muccillo-Baisch, AL; Muñoz-Serrano, AJ; Mustafa, B; Nair, GM; Nakanishi, I; Nakanjako, D; Naraparaju, K; Nawani, N; Neffati, R; Neil, EC; Neilipovitz, D; Neira-Borrajo, I; Nelson, MT; Nery, PB; Nese, M; Nguyen, F; Nguyen, MH; Niazy, AA; Nicolaï, J; Nogueira, F; Norbäck, D; Novaretti, JV; O'Donnell, T; O'Dowd, A; O'Malley, DM; Oaknin, A; Ogata, K; Ohkubo, K; Ojha, M; Olaleye, MT; Olawande, B; Olomo, EJ; Ong, EWY; Ono, A; Onwumere, J; Ortiz Bibriesca, DM; Ou, X; Oza, AM; Ozturk, K; Özütemiz, C; Palacio-Pastrana, C; Palaparthi, A; Palevsky, PM; Pan, K; Pantanetti, S; Papachristou, DJ; Pariani, A; Parikh, CR; Parissis, J; Paroul, N; Parry, S; Patel, N; Patel, SM; Patel, VC; Pawar, S; Pefura-Yone, EW; Peixoto Andrade, BCO; Pelepenko, LE; Peña-Lora, D; Peng, S; Pérez-Moro, OS; Perez-Ortiz, AC; Perry, LM; Peter, CM; Phillips, NJ; Phillips, P; Pia Tek, J; Piner, LW; Pinto, EA; Pinto, SN; Piyachaturawat, P; Poka-Mayap, V; Polledri, E; Poloni, TE; Ponessa, G; Poole, ST; Post, AK; Potter, TM; Pressly, BB; Prouty, MG; Prudêncio, M; Pulkki, K; Pupier, C; Qian, H; Qian, ZP; Qiu, Y; Qu, G; Rahimi, S; Rahman, AU; Ramadan, H; Ramanna, S; Ramirez, I; Randolph, GJ; Rasheed, A; Rault, J; Raviprakash, V; Reale, E; Redpath, C; Rema, V; Remucal, CK; Remy, D; Ren, T; Ribeiro, LB; Riboli, G; Richards, J; Rieger, V; Rieusset, J; Riva, A; Rivabella Maknis, T; Robbins, JL; Robinson, CV; Roche-Campo, F; Rodriguez, R; Rodríguez-de-Cía, J; Rollenhagen, JE; Rosen, EP; Rub, D; Rubin, N; Rubin, NT; Ruurda, JP; Saad, O; Sabell, T; Saber, SE; Sabet, M; Sadek, MM; Saejio, A; Salinas, RM; Saliu, IO; Sande, D; Sang, D; Sangenito, LS; Santos, ALSD; Sarmiento Caldas, MC; Sassaroli, S; Sassi, V; Sato, J; Sauaia, A; Saunders, K; Saunders, PR; Savarino, SJ; Scambia, G; Scanlon, N; Schetinger, MR; Schinkel, AFL; Schladweiler, MC; Schofield, CJ; Schuepbach, RA; Schulz, J; Schwartz, N; Scorcella, C; Seeley, J; Seemann, F; Seinige, D; Sengoku, T; Seravalli, J; Sgromo, B; Shaheen, MY; Shan, L; Shanmugam, S; Shao, H; Sharma, S; Shaw, KJ; Shen, BQ; Shen, CH; Shen, P; Shen, S; Shen, Y; Shen, Z; Shi, J; Shi-Li, L; Shimoda, K; Shoji, Y; Shun, C; Silva, MA; Silva-Cardoso, J; Simas, NK; Simirgiotis, MJ; Sincock, SA; Singh, MP; Sionis, A; Siu, J; Sivieri, EM; Sjerps, MJ; Skoczen, SL; Slabon, A; Slette, IJ; Smith, MD; Smith, S; Smith, TG; Snapp, KS; Snow, SJ; Soares, MCF; Soberman, D; Solares, MD; Soliman, I; Song, J; Sorooshian, A; Sorrell, TC; Spinar, J; Staudt, A; Steinhart, C; Stern, ST; Stevens, DM; Stiers, KM; Stimming, U; Su, YG; Subbian, V; Suga, H; Sukhija-Cohen, A; Suksamrarn, A; Suksen, K; Sun, J; Sun, M; Sun, P; Sun, W; Sun, XF; Sun, Y; Sundell, J; Susan, LF; Sutjarit, N; Swamy, KV; Swisher, EM; Sykes, C; Takahashi, JA; Talmor, DS; Tan, B; Tan, ZK; Tang, L; Tang, S; Tanner, JJ; Tanwar, M; Tarazi, Z; Tarvasmäki, T; Tay, FR; Teketel, A; Temitayo, GI; Thersleff, T; Thiessen Philbrook, H; Thompson, LC; Thongon, N; Tian, B; Tian, F; Tian, Q; Timothy, AT; Tingle, MD; Titze, IR; Tolppanen, H; Tong, W; Toyoda, H; Tronconi, L; Tseng, CH; Tu, H; Tu, YJ; Tung, SY; Turpault, S; Tuynman, JB; Uemoto, AT; Ugurlu, M; Ullah, S; Underwood, RS; Ungell, AL; Usandizaga-Elio, I; Vakonakis, I; van Boxel, GI; van den Beucken, JJJP; van der Boom, T; van Slegtenhorst, MA; Vanni, JR; Vaquera, A; Vasconcellos, RS; Velayos, M; Vena, R; Ventura, G; Verso, MG; Vincent, RP; Vitale, F; Vitali, S; Vlek, SL; Vleugels, MPH; Volkmann, N; Vukelic, M; Wagner Mackenzie, B; Wairagala, P; Waller, SB; Wan, J; Wan, MT; Wan, Y; Wang, CC; Wang, H; Wang, J; Wang, JF; Wang, K; Wang, L; Wang, M; Wang, S; Wang, WM; Wang, X; Wang, Y; Wang, YD; Wang, YF; Wang, Z; Wang, ZG; Warriner, K; Weberpals, JI; Weerachayaphorn, J; Wehrli, FW; Wei, J; Wei, KL; Weinheimer, CJ; Weisbord, SD; Wen, S; Wendel Garcia, PD; Williams, JW; Williams, R; Winkler, C; Wirman, AP; Wong, S; Woods, CM; Wu, B; Wu, C; Wu, F; Wu, P; Wu, S; Wu, Y; Wu, YN; Wu, ZH; Wurtzel, JGT; Xia, L; Xia, Z; Xia, ZZ; Xiao, H; Xie, C; Xin, ZM; Xing, Y; Xing, Z; Xu, S; Xu, SB; Xu, T; Xu, X; Xu, Y; Xue, L; Xun, J; Yaffe, MB; Yalew, A; Yamamoto, S; Yan, D; Yan, H; Yan, S; Yan, X; Yang, AD; Yang, E; Yang, H; Yang, J; Yang, JL; Yang, K; Yang, M; Yang, P; Yang, Q; Yang, S; Yang, W; Yang, X; Yang, Y; Yao, JC; Yao, WL; Yao, Y; Yaqub, TB; Ye, J; Ye, W; Yen, CW; Yeter, HH; Yin, C; Yip, V; Yong-Yi, J; Yu, HJ; Yu, MF; Yu, S; Yu, W; Yu, WW; Yu, X; Yuan, P; Yuan, Q; Yue, XY; Zaia, AA; Zakhary, SY; Zalwango, F; Zamalloa, A; Zamparo, P; Zampini, IC; Zani, JL; Zeitoun, R; Zeng, N; Zenteno, JC; Zepeda-Palacio, C; Zhai, C; Zhang, B; Zhang, G; Zhang, J; Zhang, K; Zhang, Q; Zhang, R; Zhang, T; Zhang, X; Zhang, Y; Zhang, YY; Zhao, B; Zhao, D; Zhao, G; Zhao, H; Zhao, Q; Zhao, R; Zhao, S; Zhao, T; Zhao, X; Zhao, XA; Zhao, Y; Zhao, Z; Zheng, Z; Zhi-Min, G; Zhou, CL; Zhou, HD; Zhou, J; Zhou, W; Zhou, XQ; Zhou, Z; Zhu, C; Zhu, H; Zhu, L; Zhu, Y; Zitzmann, N; Zou, L; Zou, Y, 2022)	0.72
" The BaP dose-response relationship suggested that Polζ plays a central role in TLS when protective mechanisms against BaP mutagenesis, such as error-free TLS, are saturated."	( The role of DNA polymerase ζ in benzo[a]pyrene-induced mutagenesis in the mouse lung. Grúz, P; Ishii, Y; Masumura, K; Nohmi, T; Ogawa, K; Takasu, S; Umemura, T, 2021)	0.62
" The absorbance decreased significantly over time following treatment with each endocrine disruptor at the concentration confirmed by the dose-response analysis."	( Effects of polycyclic aromatic hydrocarbons on the proliferation and differentiation of placental cells. Choi, SK; Jo, HG; Jo, YS; Kim, AY; Kim, WJ; Ko, HS, 2022)	0.72
"Two prototypical genotoxicants, benzo[a]pyrene (B[a]P) and colchicine (COL), were selected as model compounds to deduce their quantitative genotoxic dose-response relationship at low doses in a multi-endpoint genotoxicity assessment platform."	( Characterization of benzo[a]pyrene and colchicine based on an in vivo repeat-dosing multi-endpoint genotoxicity quantitative assessment platform. Chen, J; Chen, Y; Huo, J; Li, R; Liu, Y; Zeng, Z; Zhang, L; Zhu, X, 2022)	0.72
" We orally dosed timed-pregnant female mice with 0 or 2 mg/kg-day BaP in oil from E6."	( Gestational Benzo[a]pyrene Exposure Destroys F1 Ovarian Germ Cells Through Mitochondrial Apoptosis Pathway and Diminishes Surviving Oocyte Quality. Lee, M; Leon Parada, K; Luderer, U; Malott, KF; Swanson, E, 2022)	0.72
"Compared with mono-culture, cell proliferation increased, apoptosis decreased, and DNA damage decreased in a dose-response relationship in co-culture."	( Acute cytotoxicity test of PM Chen, Y; Du, Y; Huang, Z; Liang, L; Liu, J; Liu, Y; Xie, R; Yang, Q; Zhou, J; Zou, H, 2022)	0.72
" PAH congeners were spiked in silicon rubber membrane (SRMs) and were then introduced into the cell medium by the passive dosing method to reach a freely dissolved concentration for BeWo cell exposure."	( Effects of polycyclic aromatic hydrocarbons on gestational hormone production in a placental cell line: Application of passive dosing to in vitro tests. Alzate B, V; García L, JJ; Gil, VC; Molina P, FJ; Noreña, E; Porras, J; Quintana-Castillo, JC; Ramos-Contreras, C; Sanchez, JB; Tavera, EA; Valderrama, JFN, 2022)	0.72
" But long-term exposure to BaP or exposure to a high dosage of BaP could decrease OCR associated with maximal respiratory, spare capacity, and glycolysis metabolism."	( Benzo(a)pyrene-induced mitochondrial respiration and glycolysis disturbance in human neuroblastoma cells. Cheng, L; Li, Z; Lyu, Y; Yang, J; Zheng, J, 2023)	2.35
" Indeed, in some of the multi-dose animal studies, maximal adverse effects were observed at lower B[a]P doses, according to a non-monotonic dose-response curve typical of endocrine-disrupting compounds."	( Developmental exposure to polycyclic aromatic hydrocarbons (PAHs): Focus on benzo[a]pyrene neurotoxicity. Racca, A; Ricceri, L; Tartaglione, AM, 2023)	0.91
" Here, we used passive dosing and fluorescence-based techniques confirm the partial solubilization of BaPs adsorbed on CNTs by PS in simulated alveolar fluid."	( Dual role of pulmonary surfactant corona in modulating carbon nanotube toxicity and benzo[a]pyrene bioaccessibility. Hu, G; Luo, Z; Xu, D; Xu, Y; Yue, T; Zhao, J, 2023)	0.91
" The extremely high sensitivity of accelerator mass spectrometry (AMS) allows for dosing humans with known carcinogens with de minimus risk."	( Impact of phenanthrene co-administration on the toxicokinetics of benzo[a]pyrene in humans. UPLC-accelerator mass spectrometry following oral microdosing. Anderson, KA; Labut, EM; Maier, MLV; Ognibene, TJ; Pennington, JM; Siddens, LK; Smith, JN; Tidwell, LG; Tilton, SC; Turteltaub, KW; Uesugi, SL; Vertel, EA; Williams, DE, 2023)	0.91

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.
mouse metabolite	Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
[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
ortho- and peri-fused polycyclic arene
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathway	Proteins	Compounds
Benzo(a)pyrene metabolism	0	5

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Chain A, JmjC domain-containing histone demethylation protein 3A	Homo sapiens (human)	Potency	12.5893	0.6310	35.7641	100.0000	AID504339
Luciferase	Photinus pyralis (common eastern firefly)	Potency	10.2228	0.0072	15.7588	89.3584	AID1224835
acid sphingomyelinase	Homo sapiens (human)	Potency	25.1189	14.1254	24.0613	39.8107	AID504937
acetylcholinesterase	Homo sapiens (human)	Potency	64.5014	0.0025	41.7960	15,848.9004	AID1347395
glp-1 receptor, partial	Homo sapiens (human)	Potency	12.5893	0.0184	6.8060	14.1254	AID624417
hypoxia-inducible factor 1 alpha subunit	Homo sapiens (human)	Potency	27.6553	3.1890	29.8841	59.4836	AID1224846; AID1224894
RAR-related orphan receptor gamma	Mus musculus (house mouse)	Potency	15.4257	0.0060	38.0041	19,952.5996	AID1159521; AID1159523
SMAD family member 2	Homo sapiens (human)	Potency	33.2674	0.1737	34.3047	61.8120	AID1346859; AID1346924; AID1347035
SMAD family member 3	Homo sapiens (human)	Potency	33.2674	0.1737	34.3047	61.8120	AID1346859; AID1346924; AID1347035
GLI family zinc finger 3	Homo sapiens (human)	Potency	44.1147	0.0007	14.5928	83.7951	AID1259369
AR protein	Homo sapiens (human)	Potency	11.4719	0.0002	21.2231	8,912.5098	AID1259243; AID1259247; AID743035; AID743036; AID743042; AID743053; AID743054; AID743063
Smad3	Homo sapiens (human)	Potency	2.5119	0.0052	7.8098	29.0929	AID588855
apical membrane antigen 1, AMA1	Plasmodium falciparum 3D7	Potency	15.8489	0.7079	12.1943	39.8107	AID720542
caspase 7, apoptosis-related cysteine protease	Homo sapiens (human)	Potency	6.9917	0.0133	26.9810	70.7614	AID1346978
estrogen receptor 2 (ER beta)	Homo sapiens (human)	Potency	33.7547	0.0006	57.9133	22,387.1992	AID1259377; AID1259378; AID1259394
nuclear receptor subfamily 1, group I, member 3	Homo sapiens (human)	Potency	13.0376	0.0010	22.6508	76.6163	AID1224838; AID1224839; AID1224893
progesterone receptor	Homo sapiens (human)	Potency	46.8061	0.0004	17.9460	75.1148	AID1346784; AID1346795
glucocorticoid receptor [Homo sapiens]	Homo sapiens (human)	Potency	11.9128	0.0002	14.3764	60.0339	AID720691; AID720692; AID720719
retinoic acid nuclear receptor alpha variant 1	Homo sapiens (human)	Potency	17.3847	0.0030	41.6115	22,387.1992	AID1159552; AID1159553; AID1159555
retinoid X nuclear receptor alpha	Homo sapiens (human)	Potency	22.2986	0.0008	17.5051	59.3239	AID1159527
estrogen-related nuclear receptor alpha	Homo sapiens (human)	Potency	23.4828	0.0015	30.6073	15,848.9004	AID1224841; AID1224842; AID1224848; AID1224849; AID1259401; AID1259403
farnesoid X nuclear receptor	Homo sapiens (human)	Potency	38.5190	0.3758	27.4851	61.6524	AID743217; AID743220; AID743239
pregnane X nuclear receptor	Homo sapiens (human)	Potency	5.5537	0.0054	28.0263	1,258.9301	AID1346982
estrogen nuclear receptor alpha	Homo sapiens (human)	Potency	15.2006	0.0002	29.3054	16,493.5996	AID1259244; AID1259248; AID743069; AID743075; AID743077; AID743078; AID743079; AID743080; AID743091
peroxisome proliferator-activated receptor delta	Homo sapiens (human)	Potency	32.2732	0.0010	24.5048	61.6448	AID743212; AID743215; AID743227
peroxisome proliferator activated receptor gamma	Homo sapiens (human)	Potency	34.7074	0.0010	19.4141	70.9645	AID743094; AID743140; AID743191
vitamin D (1,25- dihydroxyvitamin D3) receptor	Homo sapiens (human)	Potency	34.5280	0.0237	23.2282	63.5986	AID743222; AID743223; AID743241
caspase-3	Homo sapiens (human)	Potency	6.9917	0.0133	26.9810	70.7614	AID1346978
aryl hydrocarbon receptor	Homo sapiens (human)	Potency	1.6069	0.0007	23.0674	1,258.9301	AID743085; AID743122
cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_a	Homo sapiens (human)	Potency	31.2308	0.0017	23.8393	78.1014	AID743083
activating transcription factor 6	Homo sapiens (human)	Potency	29.3565	0.1434	27.6121	59.8106	AID1159516; AID1159519
nuclear factor of kappa light polypeptide gene enhancer in B-cells 1 (p105), isoform CRA_a	Homo sapiens (human)	Potency	56.0115	19.7391	45.9784	64.9432	AID1159509
v-jun sarcoma virus 17 oncogene homolog (avian)	Homo sapiens (human)	Potency	25.0194	0.0578	21.1097	61.2679	AID1159526
chromobox protein homolog 1	Homo sapiens (human)	Potency	39.8107	0.0060	26.1688	89.1251	AID540317
nuclear factor erythroid 2-related factor 2 isoform 2	Homo sapiens (human)	Potency	18.3564	0.0041	9.9848	25.9290	AID504444
thyroid hormone receptor beta isoform 2	Rattus norvegicus (Norway rat)	Potency	0.1589	0.0003	23.4451	159.6830	AID743065; AID743067
heat shock protein beta-1	Homo sapiens (human)	Potency	30.0660	0.0420	27.3789	61.6448	AID743210; AID743228
importin subunit beta-1 isoform 1	Homo sapiens (human)	Potency	8.3591	5.8048	36.1306	65.1308	AID540253; AID540263
snurportin-1	Homo sapiens (human)	Potency	8.3591	5.8048	36.1306	65.1308	AID540253; AID540263
nuclear factor erythroid 2-related factor 2 isoform 1	Homo sapiens (human)	Potency	34.3944	0.0006	27.2152	1,122.0200	AID743202; AID743219
peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens (human)	Potency	84.9214	0.4256	12.0591	28.1838	AID504891
GTP-binding nuclear protein Ran isoform 1	Homo sapiens (human)	Potency	2.5929	5.8048	16.9962	25.9290	AID540253
DNA polymerase iota isoform a (long)	Homo sapiens (human)	Potency	89.1251	0.0501	27.0736	89.1251	AID588590
geminin	Homo sapiens (human)	Potency	13.2005	0.0046	11.3741	33.4983	AID624296; AID624297
DNA dC->dU-editing enzyme APOBEC-3F isoform a	Homo sapiens (human)	Potency	4.4668	0.0259	11.2398	31.6228	AID602313
Voltage-dependent calcium channel gamma-2 subunit	Mus musculus (house mouse)	Potency	0.9876	0.0015	57.7890	15,848.9004	AID1259244
Cellular tumor antigen p53	Homo sapiens (human)	Potency	3.7949	0.0023	19.5956	74.0614	AID651631; AID720552
Glutamate receptor 2	Rattus norvegicus (Norway rat)	Potency	0.9876	0.0015	51.7393	15,848.9004	AID1259244
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)	IC50 (µMol)	41.5030	0.0001	0.5453	10.0000	AID625186
Cytochrome P450 1A2	Homo sapiens (human)	IC50 (µMol)	0.0400	0.0001	1.7740	10.0000	AID625245
Tyrosine-protein kinase Fyn	Homo sapiens (human)	IC50 (µMol)	26.2350	0.0002	1.6789	8.6800	AID625185
Amine oxidase [flavin-containing] A	Homo sapiens (human)	IC50 (µMol)	5.9720	0.0000	2.3789	9.7700	AID625150
Acetylcholinesterase	Homo sapiens (human)	IC50 (µMol)	28.0000	0.0000	0.9332	10.0000	AID625193
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Aryl hydrocarbon receptor	Homo sapiens (human)	EC50 (µMol)	1.3525	0.0015	1.9769	10.0000	AID39218; AID458180
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
cell surface receptor signaling pathway	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
positive regulation of protein phosphorylation	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
protein phosphorylation	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
signal transduction	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
enzyme-linked receptor protein signaling pathway	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
cell surface receptor protein tyrosine kinase signaling pathway	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
heart development	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
neuromuscular junction development	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
motor neuron axon guidance	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
Schwann cell development	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
peptidyl-tyrosine phosphorylation	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
positive regulation of cell growth	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
regulation of microtubule-based process	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
immature T cell proliferation in thymus	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
negative regulation of immature T cell proliferation in thymus	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
positive regulation of Rho protein signal transduction	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
intracellular signal transduction	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
ERBB2-ERBB3 signaling pathway	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
ERBB2-EGFR signaling pathway	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
ERBB2-ERBB4 signaling pathway	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
wound healing	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
myelination	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
positive regulation of MAP kinase activity	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
phosphatidylinositol 3-kinase/protein kinase B signal transduction	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
positive regulation of translation	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
regulation of angiogenesis	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
positive regulation of cell adhesion	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
positive regulation of transcription by RNA polymerase I	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
oligodendrocyte differentiation	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
positive regulation of epithelial cell proliferation	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
regulation of ERK1 and ERK2 cascade	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
cellular response to growth factor stimulus	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
cellular response to epidermal growth factor stimulus	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
semaphorin-plexin signaling pathway	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
positive regulation of protein targeting to membrane	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
neurotransmitter receptor localization to postsynaptic specialization membrane	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
neurogenesis	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
positive regulation of MAPK cascade	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
negative regulation of apoptotic process	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
positive regulation of kinase activity	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
multicellular organism development	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
positive regulation of cell population proliferation	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
neuron differentiation	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
negative regulation of cell population proliferation	Cellular tumor antigen p53	Homo sapiens (human)
regulation of cell cycle	Cellular tumor antigen p53	Homo sapiens (human)
regulation of cell cycle G2/M phase transition	Cellular tumor antigen p53	Homo sapiens (human)
DNA damage response	Cellular tumor antigen p53	Homo sapiens (human)
ER overload response	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to glucose starvation	Cellular tumor antigen p53	Homo sapiens (human)
intrinsic apoptotic signaling pathway in response to DNA damage by p53 class mediator	Cellular tumor antigen p53	Homo sapiens (human)
regulation of apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of transcription by RNA polymerase II	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of miRNA transcription	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of transcription by RNA polymerase II	Cellular tumor antigen p53	Homo sapiens (human)
mitophagy	Cellular tumor antigen p53	Homo sapiens (human)
in utero embryonic development	Cellular tumor antigen p53	Homo sapiens (human)
somitogenesis	Cellular tumor antigen p53	Homo sapiens (human)
release of cytochrome c from mitochondria	Cellular tumor antigen p53	Homo sapiens (human)
hematopoietic progenitor cell differentiation	Cellular tumor antigen p53	Homo sapiens (human)
T cell proliferation involved in immune response	Cellular tumor antigen p53	Homo sapiens (human)
B cell lineage commitment	Cellular tumor antigen p53	Homo sapiens (human)
T cell lineage commitment	Cellular tumor antigen p53	Homo sapiens (human)
response to ischemia	Cellular tumor antigen p53	Homo sapiens (human)
nucleotide-excision repair	Cellular tumor antigen p53	Homo sapiens (human)
double-strand break repair	Cellular tumor antigen p53	Homo sapiens (human)
regulation of DNA-templated transcription	Cellular tumor antigen p53	Homo sapiens (human)
regulation of transcription by RNA polymerase II	Cellular tumor antigen p53	Homo sapiens (human)
protein import into nucleus	Cellular tumor antigen p53	Homo sapiens (human)
autophagy	Cellular tumor antigen p53	Homo sapiens (human)
DNA damage response	Cellular tumor antigen p53	Homo sapiens (human)
DNA damage response, signal transduction by p53 class mediator resulting in cell cycle arrest	Cellular tumor antigen p53	Homo sapiens (human)
DNA damage response, signal transduction by p53 class mediator resulting in transcription of p21 class mediator	Cellular tumor antigen p53	Homo sapiens (human)
transforming growth factor beta receptor signaling pathway	Cellular tumor antigen p53	Homo sapiens (human)
Ras protein signal transduction	Cellular tumor antigen p53	Homo sapiens (human)
gastrulation	Cellular tumor antigen p53	Homo sapiens (human)
neuroblast proliferation	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of neuroblast proliferation	Cellular tumor antigen p53	Homo sapiens (human)
protein localization	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of DNA replication	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of cell population proliferation	Cellular tumor antigen p53	Homo sapiens (human)
determination of adult lifespan	Cellular tumor antigen p53	Homo sapiens (human)
mRNA transcription	Cellular tumor antigen p53	Homo sapiens (human)
rRNA transcription	Cellular tumor antigen p53	Homo sapiens (human)
response to salt stress	Cellular tumor antigen p53	Homo sapiens (human)
response to inorganic substance	Cellular tumor antigen p53	Homo sapiens (human)
response to X-ray	Cellular tumor antigen p53	Homo sapiens (human)
response to gamma radiation	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of gene expression	Cellular tumor antigen p53	Homo sapiens (human)
cardiac muscle cell apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of cardiac muscle cell apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
glial cell proliferation	Cellular tumor antigen p53	Homo sapiens (human)
viral process	Cellular tumor antigen p53	Homo sapiens (human)
glucose catabolic process to lactate via pyruvate	Cellular tumor antigen p53	Homo sapiens (human)
cerebellum development	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of cell growth	Cellular tumor antigen p53	Homo sapiens (human)
DNA damage response, signal transduction by p53 class mediator	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of transforming growth factor beta receptor signaling pathway	Cellular tumor antigen p53	Homo sapiens (human)
mitotic G1 DNA damage checkpoint signaling	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of telomere maintenance via telomerase	Cellular tumor antigen p53	Homo sapiens (human)
T cell differentiation in thymus	Cellular tumor antigen p53	Homo sapiens (human)
tumor necrosis factor-mediated signaling pathway	Cellular tumor antigen p53	Homo sapiens (human)
regulation of tissue remodeling	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to UV	Cellular tumor antigen p53	Homo sapiens (human)
multicellular organism growth	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of mitochondrial membrane permeability	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to glucose starvation	Cellular tumor antigen p53	Homo sapiens (human)
intrinsic apoptotic signaling pathway in response to DNA damage by p53 class mediator	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
entrainment of circadian clock by photoperiod	Cellular tumor antigen p53	Homo sapiens (human)
mitochondrial DNA repair	Cellular tumor antigen p53	Homo sapiens (human)
regulation of DNA damage response, signal transduction by p53 class mediator	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of neuron apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
transcription initiation-coupled chromatin remodeling	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of proteolysis	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of DNA-templated transcription	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of DNA-templated transcription	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of RNA polymerase II transcription preinitiation complex assembly	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of transcription by RNA polymerase II	Cellular tumor antigen p53	Homo sapiens (human)
response to antibiotic	Cellular tumor antigen p53	Homo sapiens (human)
fibroblast proliferation	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of fibroblast proliferation	Cellular tumor antigen p53	Homo sapiens (human)
circadian behavior	Cellular tumor antigen p53	Homo sapiens (human)
bone marrow development	Cellular tumor antigen p53	Homo sapiens (human)
embryonic organ development	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of peptidyl-tyrosine phosphorylation	Cellular tumor antigen p53	Homo sapiens (human)
protein stabilization	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of helicase activity	Cellular tumor antigen p53	Homo sapiens (human)
protein tetramerization	Cellular tumor antigen p53	Homo sapiens (human)
chromosome organization	Cellular tumor antigen p53	Homo sapiens (human)
neuron apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
regulation of cell cycle	Cellular tumor antigen p53	Homo sapiens (human)
hematopoietic stem cell differentiation	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of glial cell proliferation	Cellular tumor antigen p53	Homo sapiens (human)
type II interferon-mediated signaling pathway	Cellular tumor antigen p53	Homo sapiens (human)
cardiac septum morphogenesis	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of programmed necrotic cell death	Cellular tumor antigen p53	Homo sapiens (human)
protein-containing complex assembly	Cellular tumor antigen p53	Homo sapiens (human)
intrinsic apoptotic signaling pathway in response to endoplasmic reticulum stress	Cellular tumor antigen p53	Homo sapiens (human)
thymocyte apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of thymocyte apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
necroptotic process	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to hypoxia	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to xenobiotic stimulus	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to ionizing radiation	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to gamma radiation	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to UV-C	Cellular tumor antigen p53	Homo sapiens (human)
stem cell proliferation	Cellular tumor antigen p53	Homo sapiens (human)
signal transduction by p53 class mediator	Cellular tumor antigen p53	Homo sapiens (human)
intrinsic apoptotic signaling pathway by p53 class mediator	Cellular tumor antigen p53	Homo sapiens (human)
reactive oxygen species metabolic process	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to actinomycin D	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of release of cytochrome c from mitochondria	Cellular tumor antigen p53	Homo sapiens (human)
cellular senescence	Cellular tumor antigen p53	Homo sapiens (human)
replicative senescence	Cellular tumor antigen p53	Homo sapiens (human)
oxidative stress-induced premature senescence	Cellular tumor antigen p53	Homo sapiens (human)
intrinsic apoptotic signaling pathway	Cellular tumor antigen p53	Homo sapiens (human)
oligodendrocyte apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of execution phase of apoptosis	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of mitophagy	Cellular tumor antigen p53	Homo sapiens (human)
regulation of mitochondrial membrane permeability involved in apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
regulation of intrinsic apoptotic signaling pathway by p53 class mediator	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of miRNA transcription	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of G1 to G0 transition	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of miRNA processing	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of glucose catabolic process to lactate via pyruvate	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of pentose-phosphate shunt	Cellular tumor antigen p53	Homo sapiens (human)
intrinsic apoptotic signaling pathway in response to hypoxia	Cellular tumor antigen p53	Homo sapiens (human)
regulation of fibroblast apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of reactive oxygen species metabolic process	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of reactive oxygen species metabolic process	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of stem cell proliferation	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of cellular senescence	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of intrinsic apoptotic signaling pathway	Cellular tumor antigen p53	Homo sapiens (human)
steroid catabolic process	Cytochrome P450 1A2	Homo sapiens (human)
porphyrin-containing compound metabolic process	Cytochrome P450 1A2	Homo sapiens (human)
xenobiotic metabolic process	Cytochrome P450 1A2	Homo sapiens (human)
cholesterol metabolic process	Cytochrome P450 1A2	Homo sapiens (human)
estrogen metabolic process	Cytochrome P450 1A2	Homo sapiens (human)
toxin biosynthetic process	Cytochrome P450 1A2	Homo sapiens (human)
post-embryonic development	Cytochrome P450 1A2	Homo sapiens (human)
alkaloid metabolic process	Cytochrome P450 1A2	Homo sapiens (human)
regulation of gene expression	Cytochrome P450 1A2	Homo sapiens (human)
monoterpenoid metabolic process	Cytochrome P450 1A2	Homo sapiens (human)
dibenzo-p-dioxin metabolic process	Cytochrome P450 1A2	Homo sapiens (human)
epoxygenase P450 pathway	Cytochrome P450 1A2	Homo sapiens (human)
lung development	Cytochrome P450 1A2	Homo sapiens (human)
methylation	Cytochrome P450 1A2	Homo sapiens (human)
monocarboxylic acid metabolic process	Cytochrome P450 1A2	Homo sapiens (human)
xenobiotic catabolic process	Cytochrome P450 1A2	Homo sapiens (human)
retinol metabolic process	Cytochrome P450 1A2	Homo sapiens (human)
long-chain fatty acid biosynthetic process	Cytochrome P450 1A2	Homo sapiens (human)
cellular respiration	Cytochrome P450 1A2	Homo sapiens (human)
aflatoxin metabolic process	Cytochrome P450 1A2	Homo sapiens (human)
hydrogen peroxide biosynthetic process	Cytochrome P450 1A2	Homo sapiens (human)
oxidative demethylation	Cytochrome P450 1A2	Homo sapiens (human)
cellular response to cadmium ion	Cytochrome P450 1A2	Homo sapiens (human)
omega-hydroxylase P450 pathway	Cytochrome P450 1A2	Homo sapiens (human)
response to singlet oxygen	Tyrosine-protein kinase Fyn	Homo sapiens (human)
neuron migration	Tyrosine-protein kinase Fyn	Homo sapiens (human)
stimulatory C-type lectin receptor signaling pathway	Tyrosine-protein kinase Fyn	Homo sapiens (human)
adaptive immune response	Tyrosine-protein kinase Fyn	Homo sapiens (human)
negative regulation of inflammatory response to antigenic stimulus	Tyrosine-protein kinase Fyn	Homo sapiens (human)
heart process	Tyrosine-protein kinase Fyn	Homo sapiens (human)
protein phosphorylation	Tyrosine-protein kinase Fyn	Homo sapiens (human)
calcium ion transport	Tyrosine-protein kinase Fyn	Homo sapiens (human)
G protein-coupled glutamate receptor signaling pathway	Tyrosine-protein kinase Fyn	Homo sapiens (human)
axon guidance	Tyrosine-protein kinase Fyn	Homo sapiens (human)
learning	Tyrosine-protein kinase Fyn	Homo sapiens (human)
feeding behavior	Tyrosine-protein kinase Fyn	Homo sapiens (human)
regulation of cell shape	Tyrosine-protein kinase Fyn	Homo sapiens (human)
gene expression	Tyrosine-protein kinase Fyn	Homo sapiens (human)
negative regulation of gene expression	Tyrosine-protein kinase Fyn	Homo sapiens (human)
negative regulation of hydrogen peroxide biosynthetic process	Tyrosine-protein kinase Fyn	Homo sapiens (human)
positive regulation of neuron projection development	Tyrosine-protein kinase Fyn	Homo sapiens (human)
protein ubiquitination	Tyrosine-protein kinase Fyn	Homo sapiens (human)
peptidyl-tyrosine phosphorylation	Tyrosine-protein kinase Fyn	Homo sapiens (human)
protein catabolic process	Tyrosine-protein kinase Fyn	Homo sapiens (human)
forebrain development	Tyrosine-protein kinase Fyn	Homo sapiens (human)
T cell costimulation	Tyrosine-protein kinase Fyn	Homo sapiens (human)
negative regulation of protein ubiquitination	Tyrosine-protein kinase Fyn	Homo sapiens (human)
intracellular signal transduction	Tyrosine-protein kinase Fyn	Homo sapiens (human)
cellular response to platelet-derived growth factor stimulus	Tyrosine-protein kinase Fyn	Homo sapiens (human)
Fc-gamma receptor signaling pathway involved in phagocytosis	Tyrosine-protein kinase Fyn	Homo sapiens (human)
negative regulation of protein catabolic process	Tyrosine-protein kinase Fyn	Homo sapiens (human)
positive regulation of tyrosine phosphorylation of STAT protein	Tyrosine-protein kinase Fyn	Homo sapiens (human)
response to ethanol	Tyrosine-protein kinase Fyn	Homo sapiens (human)
vascular endothelial growth factor receptor signaling pathway	Tyrosine-protein kinase Fyn	Homo sapiens (human)
ephrin receptor signaling pathway	Tyrosine-protein kinase Fyn	Homo sapiens (human)
dendrite morphogenesis	Tyrosine-protein kinase Fyn	Homo sapiens (human)
regulation of peptidyl-tyrosine phosphorylation	Tyrosine-protein kinase Fyn	Homo sapiens (human)
activated T cell proliferation	Tyrosine-protein kinase Fyn	Homo sapiens (human)
modulation of chemical synaptic transmission	Tyrosine-protein kinase Fyn	Homo sapiens (human)
T cell receptor signaling pathway	Tyrosine-protein kinase Fyn	Homo sapiens (human)
leukocyte migration	Tyrosine-protein kinase Fyn	Homo sapiens (human)
detection of mechanical stimulus involved in sensory perception of pain	Tyrosine-protein kinase Fyn	Homo sapiens (human)
cellular response to hydrogen peroxide	Tyrosine-protein kinase Fyn	Homo sapiens (human)
cellular response to transforming growth factor beta stimulus	Tyrosine-protein kinase Fyn	Homo sapiens (human)
positive regulation of protein targeting to membrane	Tyrosine-protein kinase Fyn	Homo sapiens (human)
dendritic spine maintenance	Tyrosine-protein kinase Fyn	Homo sapiens (human)
positive regulation of protein localization to nucleus	Tyrosine-protein kinase Fyn	Homo sapiens (human)
regulation of glutamate receptor signaling pathway	Tyrosine-protein kinase Fyn	Homo sapiens (human)
negative regulation of oxidative stress-induced intrinsic apoptotic signaling pathway	Tyrosine-protein kinase Fyn	Homo sapiens (human)
negative regulation of dendritic spine maintenance	Tyrosine-protein kinase Fyn	Homo sapiens (human)
response to amyloid-beta	Tyrosine-protein kinase Fyn	Homo sapiens (human)
cellular response to amyloid-beta	Tyrosine-protein kinase Fyn	Homo sapiens (human)
cellular response to L-glutamate	Tyrosine-protein kinase Fyn	Homo sapiens (human)
cellular response to glycine	Tyrosine-protein kinase Fyn	Homo sapiens (human)
positive regulation of protein localization to membrane	Tyrosine-protein kinase Fyn	Homo sapiens (human)
regulation of calcium ion import across plasma membrane	Tyrosine-protein kinase Fyn	Homo sapiens (human)
positive regulation of cysteine-type endopeptidase activity	Tyrosine-protein kinase Fyn	Homo sapiens (human)
innate immune response	Tyrosine-protein kinase Fyn	Homo sapiens (human)
cell differentiation	Tyrosine-protein kinase Fyn	Homo sapiens (human)
cell surface receptor protein tyrosine kinase signaling pathway	Tyrosine-protein kinase Fyn	Homo sapiens (human)
biogenic amine metabolic process	Amine oxidase [flavin-containing] A	Homo sapiens (human)
positive regulation of signal transduction	Amine oxidase [flavin-containing] A	Homo sapiens (human)
dopamine catabolic process	Amine oxidase [flavin-containing] A	Homo sapiens (human)
acetylcholine catabolic process in synaptic cleft	Acetylcholinesterase	Homo sapiens (human)
regulation of receptor recycling	Acetylcholinesterase	Homo sapiens (human)
osteoblast development	Acetylcholinesterase	Homo sapiens (human)
acetylcholine catabolic process	Acetylcholinesterase	Homo sapiens (human)
cell adhesion	Acetylcholinesterase	Homo sapiens (human)
nervous system development	Acetylcholinesterase	Homo sapiens (human)
synapse assembly	Acetylcholinesterase	Homo sapiens (human)
receptor internalization	Acetylcholinesterase	Homo sapiens (human)
negative regulation of synaptic transmission, cholinergic	Acetylcholinesterase	Homo sapiens (human)
amyloid precursor protein metabolic process	Acetylcholinesterase	Homo sapiens (human)
positive regulation of protein secretion	Acetylcholinesterase	Homo sapiens (human)
retina development in camera-type eye	Acetylcholinesterase	Homo sapiens (human)
acetylcholine receptor signaling pathway	Acetylcholinesterase	Homo sapiens (human)
positive regulation of cold-induced thermogenesis	Acetylcholinesterase	Homo sapiens (human)
blood vessel development	Aryl hydrocarbon receptor	Homo sapiens (human)
regulation of adaptive immune response	Aryl hydrocarbon receptor	Homo sapiens (human)
negative regulation of T cell mediated immune response to tumor cell	Aryl hydrocarbon receptor	Homo sapiens (human)
regulation of DNA-templated transcription	Aryl hydrocarbon receptor	Homo sapiens (human)
regulation of transcription by RNA polymerase II	Aryl hydrocarbon receptor	Homo sapiens (human)
xenobiotic metabolic process	Aryl hydrocarbon receptor	Homo sapiens (human)
apoptotic process	Aryl hydrocarbon receptor	Homo sapiens (human)
response to xenobiotic stimulus	Aryl hydrocarbon receptor	Homo sapiens (human)
response to toxic substance	Aryl hydrocarbon receptor	Homo sapiens (human)
regulation of gene expression	Aryl hydrocarbon receptor	Homo sapiens (human)
cAMP-mediated signaling	Aryl hydrocarbon receptor	Homo sapiens (human)
intracellular receptor signaling pathway	Aryl hydrocarbon receptor	Homo sapiens (human)
regulation of B cell proliferation	Aryl hydrocarbon receptor	Homo sapiens (human)
circadian regulation of gene expression	Aryl hydrocarbon receptor	Homo sapiens (human)
negative regulation of DNA-templated transcription	Aryl hydrocarbon receptor	Homo sapiens (human)
positive regulation of DNA-templated transcription	Aryl hydrocarbon receptor	Homo sapiens (human)
positive regulation of transcription by RNA polymerase II	Aryl hydrocarbon receptor	Homo sapiens (human)
negative regulation of inflammatory response	Aryl hydrocarbon receptor	Homo sapiens (human)
cellular response to molecule of bacterial origin	Aryl hydrocarbon receptor	Homo sapiens (human)
cellular response to cAMP	Aryl hydrocarbon receptor	Homo sapiens (human)
cellular response to forskolin	Aryl hydrocarbon receptor	Homo sapiens (human)
cellular response to 2,3,7,8-tetrachlorodibenzodioxine	Aryl hydrocarbon receptor	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
growth factor binding	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
RNA polymerase I core binding	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
protein tyrosine kinase activity	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
transmembrane receptor protein tyrosine kinase activity	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
transmembrane signaling receptor activity	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
signaling receptor binding	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
protein binding	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
ATP binding	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
coreceptor activity	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
receptor tyrosine kinase binding	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
identical protein binding	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
ErbB-3 class receptor binding	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
protein heterodimerization activity	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
transcription cis-regulatory region binding	Cellular tumor antigen p53	Homo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA binding	Cellular tumor antigen p53	Homo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specific	Cellular tumor antigen p53	Homo sapiens (human)
cis-regulatory region sequence-specific DNA binding	Cellular tumor antigen p53	Homo sapiens (human)
core promoter sequence-specific DNA binding	Cellular tumor antigen p53	Homo sapiens (human)
TFIID-class transcription factor complex binding	Cellular tumor antigen p53	Homo sapiens (human)
DNA-binding transcription repressor activity, RNA polymerase II-specific	Cellular tumor antigen p53	Homo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specific	Cellular tumor antigen p53	Homo sapiens (human)
protease binding	Cellular tumor antigen p53	Homo sapiens (human)
p53 binding	Cellular tumor antigen p53	Homo sapiens (human)
DNA binding	Cellular tumor antigen p53	Homo sapiens (human)
chromatin binding	Cellular tumor antigen p53	Homo sapiens (human)
DNA-binding transcription factor activity	Cellular tumor antigen p53	Homo sapiens (human)
mRNA 3'-UTR binding	Cellular tumor antigen p53	Homo sapiens (human)
copper ion binding	Cellular tumor antigen p53	Homo sapiens (human)
protein binding	Cellular tumor antigen p53	Homo sapiens (human)
zinc ion binding	Cellular tumor antigen p53	Homo sapiens (human)
enzyme binding	Cellular tumor antigen p53	Homo sapiens (human)
receptor tyrosine kinase binding	Cellular tumor antigen p53	Homo sapiens (human)
ubiquitin protein ligase binding	Cellular tumor antigen p53	Homo sapiens (human)
histone deacetylase regulator activity	Cellular tumor antigen p53	Homo sapiens (human)
ATP-dependent DNA/DNA annealing activity	Cellular tumor antigen p53	Homo sapiens (human)
identical protein binding	Cellular tumor antigen p53	Homo sapiens (human)
histone deacetylase binding	Cellular tumor antigen p53	Homo sapiens (human)
protein heterodimerization activity	Cellular tumor antigen p53	Homo sapiens (human)
protein-folding chaperone binding	Cellular tumor antigen p53	Homo sapiens (human)
protein phosphatase 2A binding	Cellular tumor antigen p53	Homo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor binding	Cellular tumor antigen p53	Homo sapiens (human)
14-3-3 protein binding	Cellular tumor antigen p53	Homo sapiens (human)
MDM2/MDM4 family protein binding	Cellular tumor antigen p53	Homo sapiens (human)
disordered domain specific binding	Cellular tumor antigen p53	Homo sapiens (human)
general transcription initiation factor binding	Cellular tumor antigen p53	Homo sapiens (human)
molecular function activator activity	Cellular tumor antigen p53	Homo sapiens (human)
promoter-specific chromatin binding	Cellular tumor antigen p53	Homo sapiens (human)
monooxygenase activity	Cytochrome P450 1A2	Homo sapiens (human)
iron ion binding	Cytochrome P450 1A2	Homo sapiens (human)
protein binding	Cytochrome P450 1A2	Homo sapiens (human)
electron transfer activity	Cytochrome P450 1A2	Homo sapiens (human)
oxidoreductase activity	Cytochrome P450 1A2	Homo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen	Cytochrome P450 1A2	Homo sapiens (human)
enzyme binding	Cytochrome P450 1A2	Homo sapiens (human)
heme binding	Cytochrome P450 1A2	Homo sapiens (human)
demethylase activity	Cytochrome P450 1A2	Homo sapiens (human)
caffeine oxidase activity	Cytochrome P450 1A2	Homo sapiens (human)
aromatase activity	Cytochrome P450 1A2	Homo sapiens (human)
estrogen 16-alpha-hydroxylase activity	Cytochrome P450 1A2	Homo sapiens (human)
estrogen 2-hydroxylase activity	Cytochrome P450 1A2	Homo sapiens (human)
hydroperoxy icosatetraenoate dehydratase activity	Cytochrome P450 1A2	Homo sapiens (human)
protein tyrosine kinase activity	Tyrosine-protein kinase Fyn	Homo sapiens (human)
non-membrane spanning protein tyrosine kinase activity	Tyrosine-protein kinase Fyn	Homo sapiens (human)
protein binding	Tyrosine-protein kinase Fyn	Homo sapiens (human)
ATP binding	Tyrosine-protein kinase Fyn	Homo sapiens (human)
phospholipase activator activity	Tyrosine-protein kinase Fyn	Homo sapiens (human)
enzyme binding	Tyrosine-protein kinase Fyn	Homo sapiens (human)
type 5 metabotropic glutamate receptor binding	Tyrosine-protein kinase Fyn	Homo sapiens (human)
identical protein binding	Tyrosine-protein kinase Fyn	Homo sapiens (human)
alpha-tubulin binding	Tyrosine-protein kinase Fyn	Homo sapiens (human)
phospholipase binding	Tyrosine-protein kinase Fyn	Homo sapiens (human)
transmembrane transporter binding	Tyrosine-protein kinase Fyn	Homo sapiens (human)
metal ion binding	Tyrosine-protein kinase Fyn	Homo sapiens (human)
ephrin receptor binding	Tyrosine-protein kinase Fyn	Homo sapiens (human)
tau protein binding	Tyrosine-protein kinase Fyn	Homo sapiens (human)
tau-protein kinase activity	Tyrosine-protein kinase Fyn	Homo sapiens (human)
growth factor receptor binding	Tyrosine-protein kinase Fyn	Homo sapiens (human)
scaffold protein binding	Tyrosine-protein kinase Fyn	Homo sapiens (human)
disordered domain specific binding	Tyrosine-protein kinase Fyn	Homo sapiens (human)
signaling receptor binding	Tyrosine-protein kinase Fyn	Homo sapiens (human)
protein binding	Amine oxidase [flavin-containing] A	Homo sapiens (human)
primary amine oxidase activity	Amine oxidase [flavin-containing] A	Homo sapiens (human)
aliphatic amine oxidase activity	Amine oxidase [flavin-containing] A	Homo sapiens (human)
monoamine oxidase activity	Amine oxidase [flavin-containing] A	Homo sapiens (human)
flavin adenine dinucleotide binding	Amine oxidase [flavin-containing] A	Homo sapiens (human)
amyloid-beta binding	Acetylcholinesterase	Homo sapiens (human)
acetylcholinesterase activity	Acetylcholinesterase	Homo sapiens (human)
cholinesterase activity	Acetylcholinesterase	Homo sapiens (human)
protein binding	Acetylcholinesterase	Homo sapiens (human)
collagen binding	Acetylcholinesterase	Homo sapiens (human)
hydrolase activity	Acetylcholinesterase	Homo sapiens (human)
serine hydrolase activity	Acetylcholinesterase	Homo sapiens (human)
acetylcholine binding	Acetylcholinesterase	Homo sapiens (human)
protein homodimerization activity	Acetylcholinesterase	Homo sapiens (human)
laminin binding	Acetylcholinesterase	Homo sapiens (human)
nuclear receptor activity	Aryl hydrocarbon receptor	Homo sapiens (human)
transcription cis-regulatory region binding	Aryl hydrocarbon receptor	Homo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specific	Aryl hydrocarbon receptor	Homo sapiens (human)
cis-regulatory region sequence-specific DNA binding	Aryl hydrocarbon receptor	Homo sapiens (human)
TFIID-class transcription factor complex binding	Aryl hydrocarbon receptor	Homo sapiens (human)
transcription coactivator binding	Aryl hydrocarbon receptor	Homo sapiens (human)
DNA binding	Aryl hydrocarbon receptor	Homo sapiens (human)
DNA-binding transcription factor activity	Aryl hydrocarbon receptor	Homo sapiens (human)
nuclear receptor activity	Aryl hydrocarbon receptor	Homo sapiens (human)
protein binding	Aryl hydrocarbon receptor	Homo sapiens (human)
TBP-class protein binding	Aryl hydrocarbon receptor	Homo sapiens (human)
protein homodimerization activity	Aryl hydrocarbon receptor	Homo sapiens (human)
protein heterodimerization activity	Aryl hydrocarbon receptor	Homo sapiens (human)
Hsp90 protein binding	Aryl hydrocarbon receptor	Homo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor binding	Aryl hydrocarbon receptor	Homo sapiens (human)
E-box binding	Aryl hydrocarbon receptor	Homo sapiens (human)
sequence-specific double-stranded DNA binding	Aryl hydrocarbon receptor	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
semaphorin receptor complex	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
nucleus	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
nucleoplasm	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
early endosome	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
cytosol	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
plasma membrane	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
endosome membrane	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
membrane	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
basolateral plasma membrane	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
apical plasma membrane	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
neuromuscular junction	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
ruffle membrane	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
presynaptic membrane	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
myelin sheath	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
perinuclear region of cytoplasm	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
ERBB3:ERBB2 complex	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
receptor complex	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
plasma membrane	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
basal plasma membrane	Receptor tyrosine-protein kinase erbB-2	Homo sapiens (human)
nuclear body	Cellular tumor antigen p53	Homo sapiens (human)
nucleus	Cellular tumor antigen p53	Homo sapiens (human)
nucleoplasm	Cellular tumor antigen p53	Homo sapiens (human)
replication fork	Cellular tumor antigen p53	Homo sapiens (human)
nucleolus	Cellular tumor antigen p53	Homo sapiens (human)
cytoplasm	Cellular tumor antigen p53	Homo sapiens (human)
mitochondrion	Cellular tumor antigen p53	Homo sapiens (human)
mitochondrial matrix	Cellular tumor antigen p53	Homo sapiens (human)
endoplasmic reticulum	Cellular tumor antigen p53	Homo sapiens (human)
centrosome	Cellular tumor antigen p53	Homo sapiens (human)
cytosol	Cellular tumor antigen p53	Homo sapiens (human)
nuclear matrix	Cellular tumor antigen p53	Homo sapiens (human)
PML body	Cellular tumor antigen p53	Homo sapiens (human)
transcription repressor complex	Cellular tumor antigen p53	Homo sapiens (human)
site of double-strand break	Cellular tumor antigen p53	Homo sapiens (human)
germ cell nucleus	Cellular tumor antigen p53	Homo sapiens (human)
chromatin	Cellular tumor antigen p53	Homo sapiens (human)
transcription regulator complex	Cellular tumor antigen p53	Homo sapiens (human)
protein-containing complex	Cellular tumor antigen p53	Homo sapiens (human)
endoplasmic reticulum membrane	Cytochrome P450 1A2	Homo sapiens (human)
intracellular membrane-bounded organelle	Cytochrome P450 1A2	Homo sapiens (human)
intracellular membrane-bounded organelle	Cytochrome P450 1A2	Homo sapiens (human)
membrane raft	Tyrosine-protein kinase Fyn	Homo sapiens (human)
dendrite	Tyrosine-protein kinase Fyn	Homo sapiens (human)
nucleus	Tyrosine-protein kinase Fyn	Homo sapiens (human)
mitochondrion	Tyrosine-protein kinase Fyn	Homo sapiens (human)
endosome	Tyrosine-protein kinase Fyn	Homo sapiens (human)
cytosol	Tyrosine-protein kinase Fyn	Homo sapiens (human)
actin filament	Tyrosine-protein kinase Fyn	Homo sapiens (human)
plasma membrane	Tyrosine-protein kinase Fyn	Homo sapiens (human)
postsynaptic density	Tyrosine-protein kinase Fyn	Homo sapiens (human)
dendrite	Tyrosine-protein kinase Fyn	Homo sapiens (human)
perikaryon	Tyrosine-protein kinase Fyn	Homo sapiens (human)
cell body	Tyrosine-protein kinase Fyn	Homo sapiens (human)
membrane raft	Tyrosine-protein kinase Fyn	Homo sapiens (human)
perinuclear region of cytoplasm	Tyrosine-protein kinase Fyn	Homo sapiens (human)
perinuclear endoplasmic reticulum	Tyrosine-protein kinase Fyn	Homo sapiens (human)
glial cell projection	Tyrosine-protein kinase Fyn	Homo sapiens (human)
Schaffer collateral - CA1 synapse	Tyrosine-protein kinase Fyn	Homo sapiens (human)
plasma membrane	Tyrosine-protein kinase Fyn	Homo sapiens (human)
plasma membrane	Glutamate receptor 2	Rattus norvegicus (Norway rat)
mitochondrion	Amine oxidase [flavin-containing] A	Homo sapiens (human)
mitochondrial outer membrane	Amine oxidase [flavin-containing] A	Homo sapiens (human)
cytosol	Amine oxidase [flavin-containing] A	Homo sapiens (human)
mitochondrion	Amine oxidase [flavin-containing] A	Homo sapiens (human)
extracellular region	Acetylcholinesterase	Homo sapiens (human)
basement membrane	Acetylcholinesterase	Homo sapiens (human)
extracellular space	Acetylcholinesterase	Homo sapiens (human)
nucleus	Acetylcholinesterase	Homo sapiens (human)
Golgi apparatus	Acetylcholinesterase	Homo sapiens (human)
plasma membrane	Acetylcholinesterase	Homo sapiens (human)
cell surface	Acetylcholinesterase	Homo sapiens (human)
membrane	Acetylcholinesterase	Homo sapiens (human)
neuromuscular junction	Acetylcholinesterase	Homo sapiens (human)
synaptic cleft	Acetylcholinesterase	Homo sapiens (human)
synapse	Acetylcholinesterase	Homo sapiens (human)
perinuclear region of cytoplasm	Acetylcholinesterase	Homo sapiens (human)
side of membrane	Acetylcholinesterase	Homo sapiens (human)
nucleus	Aryl hydrocarbon receptor	Homo sapiens (human)
nuclear aryl hydrocarbon receptor complex	Aryl hydrocarbon receptor	Homo sapiens (human)
nucleus	Aryl hydrocarbon receptor	Homo sapiens (human)
nucleoplasm	Aryl hydrocarbon receptor	Homo sapiens (human)
cytoplasm	Aryl hydrocarbon receptor	Homo sapiens (human)
cytosol	Aryl hydrocarbon receptor	Homo sapiens (human)
chromatin	Aryl hydrocarbon receptor	Homo sapiens (human)
transcription regulator complex	Aryl hydrocarbon receptor	Homo sapiens (human)
protein-containing complex	Aryl hydrocarbon receptor	Homo sapiens (human)
cytosolic aryl hydrocarbon receptor complex	Aryl hydrocarbon receptor	Homo sapiens (human)
aryl hydrocarbon receptor complex	Aryl hydrocarbon receptor	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Assay ID	Title	Year	Journal	Article
AID977602	Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	2013	Molecular pharmacology, Jun, Volume: 83, Issue:6	Structure-based identification of OATP1B1/3 inhibitors.
AID39218	Concentration to bind to human AhR-modied electrode	2004	Bioorganic & medicinal chemistry letters, Jan-05, Volume: 14, Issue:1	An electrochemical device for the assay of the interaction between a dioxin receptor and its various ligands.
AID977599	Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	2013	Molecular pharmacology, Jun, Volume: 83, Issue:6	Structure-based identification of OATP1B1/3 inhibitors.
AID252214	Average fold change in expression of CYP1A1 at 1 mM after co-treatment with compound and TSA in human MCF-7 cells	2005	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 15, Issue:5	Effects of suberoylanilide hydroxamic acid and trichostatin A on induction of cytochrome P450 enzymes and benzo[a]pyrene DNA adduct formation in human cells.
AID458180	Agonist activity at aryl hydrocarbon receptor in human MCF7 cells after 24 hrs CYP1A1-dependent EROD assay	2010	Bioorganic & medicinal chemistry, Feb, Volume: 18, Issue:3	beta-Naphthoflavone analogs as potent and soluble aryl hydrocarbon receptor agonists: improvement of solubility by disruption of molecular planarity.
AID252222	Average fold change in expression of CYP1A1 after co-treatment with compound of concentration 1 mM in human MCF-7 cells	2005	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 15, Issue:5	Effects of suberoylanilide hydroxamic acid and trichostatin A on induction of cytochrome P450 enzymes and benzo[a]pyrene DNA adduct formation in human cells.
AID603957	Octanol-water partition coefficient, log P of the compound	2008	European journal of medicinal chemistry, Apr, Volume: 43, Issue:4	QSPR modeling of octanol/water partition coefficient for vitamins by optimal descriptors calculated with SMILES.
AID189501	Rate of hydroxylation by liver microsomes in rats induced with 3-MC; Rates are expressed as pmol of product per 30 min per mg of protein	1980	Journal of medicinal chemistry, Aug, Volume: 23, Issue:8	Metabolism of 6-substituted benzo[a]pyrene derivatives: O-dealkylation and regiospecificity in aromatic hydroxylation.
AID252219	Average fold change in expression of CYP1B1 after treatment with compound of concentration 1 mM in human MCF-7 cells	2005	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 15, Issue:5	Effects of suberoylanilide hydroxamic acid and trichostatin A on induction of cytochrome P450 enzymes and benzo[a]pyrene DNA adduct formation in human cells.
AID252215	Average fold change in expression of CYP1B1 at 1 mM after co-treatment with compound and TSA in human MCF-7 cells	2005	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 15, Issue:5	Effects of suberoylanilide hydroxamic acid and trichostatin A on induction of cytochrome P450 enzymes and benzo[a]pyrene DNA adduct formation in human cells.
AID252224	Average fold change in expression of CYP1B1 after co-treatment with compound of concentration 1 mM in human MCF-7 cells	2005	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 15, Issue:5	Effects of suberoylanilide hydroxamic acid and trichostatin A on induction of cytochrome P450 enzymes and benzo[a]pyrene DNA adduct formation in human cells.
AID39092	Compound tested for its binding to human Orphan receptor (AhR); Active	2004	Bioorganic & medicinal chemistry letters, Jan-05, Volume: 14, Issue:1	An electrochemical device for the assay of the interaction between a dioxin receptor and its various ligands.
AID465491	Mutagenic activity in Salmonella Typhimurium TA100 assessed as increase in number of revertants at 0.5 ug/plate by Ames test presence of S9 fraction (Rvb=124+/-13)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID1459079	Mutagenicity in Salmonella typhimurium TA100 assessed as revertant colonies/plate in presence of liver S9 fraction at 2 ug/plate by Ames test (Rvb = 129 +/- 3 No_unit)	2017	European journal of medicinal chemistry, Jan-05, Volume: 125	New potent biaryl sulfate-based hepatitis C virus inhibitors.
AID465501	Mutagenic activity in Salmonella Typhimurium TA102 assessed as increase in number of revertants at 0.5 ug/plate by Ames test presence of S9 fraction (Rvb=369+/-34)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID713040	Genotoxicity in human HepG2 cells assessed as micronuclei formation at 50 uM after 24 hrs by DAPI staining	2012	Journal of medicinal chemistry, Oct-11, Volume: 55, Issue:19	Optimization of a small tropomyosin-related kinase B (TrkB) agonist 7,8-dihydroxyflavone active in mouse models of depression.
AID252221	Average fold change in expression of CYP1B1 after treatment with compound of concentration 0.1 mM in human MCF-7 cells	2005	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 15, Issue:5	Effects of suberoylanilide hydroxamic acid and trichostatin A on induction of cytochrome P450 enzymes and benzo[a]pyrene DNA adduct formation in human cells.
AID1897744	Inhibition of Hedgehog-signalling dependent purmorphamine induced osteoblast differentiation in mouse C3H 10T1/2 cells assessed as reduction in ALP expression at 0.01 to 100 uM incubated for 96 hrs by CDP-Star luminogenic substrate based assay	2022	Journal of medicinal chemistry, 12-22, Volume: 65, Issue:24	The Highly Potent AhR Agonist Picoberin Modulates Hh-Dependent Osteoblast Differentiation.
AID249991	Mean B[a]P DNA binding at 4 uM in human MCF-7 cells	2005	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 15, Issue:5	Effects of suberoylanilide hydroxamic acid and trichostatin A on induction of cytochrome P450 enzymes and benzo[a]pyrene DNA adduct formation in human cells.
AID1320140	Cytotoxicity against CHL cells assessed as structural aberrations at 20 ug/ml preincubated for 6 hrs followed by 18 hrs incubation in fresh medium in presence of S9 fraction by Giemsa-staining-based microscopic analysis	2016	Bioorganic & medicinal chemistry, 11-01, Volume: 24, Issue:21	Phosphonate-based irreversible inhibitors of human γ-glutamyl transpeptidase (GGT). GGsTop is a non-toxic and highly selective inhibitor with critical electrostatic interaction with an active-site residue Lys562 for enhanced inhibitory activity.
AID680127	TP_TRANSPORTER: transepithelial transport (basal to apical) in MDR1-expressing LLC-PK1 cells	1998	Archives of biochemistry and biophysics, Feb-15, Volume: 350, Issue:2	Human MDR1 and mouse mdr1a P-glycoprotein alter the cellular retention and disposition of erythromycin, but not of retinoic acid or benzo(a)pyrene.
AID1241897	Genotoxicity in Salmonella typhimurium TA100 assessed as induction of revertant colonies at 2 ug/plate in presence of S9 mix by Ames test relative untreated control	2015	European journal of medicinal chemistry, Aug-28, Volume: 101	Novel benzidine and diaminofluorene prolinamide derivatives as potent hepatitis C virus NS5A inhibitors.
AID1320144	Cytotoxicity against CHL cells assessed as chromatid gap at 20 ug/ml preincubated for 6 hrs followed by 18 hrs incubation in fresh medium in presence of S9 fraction by Giemsa-staining-based microscopic analysis	2016	Bioorganic & medicinal chemistry, 11-01, Volume: 24, Issue:21	Phosphonate-based irreversible inhibitors of human γ-glutamyl transpeptidase (GGT). GGsTop is a non-toxic and highly selective inhibitor with critical electrostatic interaction with an active-site residue Lys562 for enhanced inhibitory activity.
AID160321	Competition for [3H]benzo[a]pyrene-binding site of polycyclic aromatic hydrocarbon binding protein (PBP) from mouse liver	1990	Journal of medicinal chemistry, Feb, Volume: 33, Issue:2	Voronoi binding site model of a polycyclic aromatic hydrocarbon binding protein.
AID1459077	Mutagenicity in Salmonella typhimurium TA98 assessed as revertant colonies/plate in presence of liver S9 fraction at 2 ug/plate by Ames test (Rvb = 25 +/- 3 No_unit)	2017	European journal of medicinal chemistry, Jan-05, Volume: 125	New potent biaryl sulfate-based hepatitis C virus inhibitors.
AID252216	Average fold change in expression of CYP1A1 at 1 mM after co-treatment with compound and SAHA in human MCF-7 cells	2005	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 15, Issue:5	Effects of suberoylanilide hydroxamic acid and trichostatin A on induction of cytochrome P450 enzymes and benzo[a]pyrene DNA adduct formation in human cells.
AID189496	Rate of 3-hydroxylation by lung microsomes in rats induced with PB; Rates are expressed as pmol of product per 30 min per mg of protein	1980	Journal of medicinal chemistry, Aug, Volume: 23, Issue:8	Metabolism of 6-substituted benzo[a]pyrene derivatives: O-dealkylation and regiospecificity in aromatic hydroxylation.
AID465471	Mutagenic activity in Salmonella Typhimurium TA98 assessed as increase in number of revertants at 0.5 ug/plate by Ames test presence of S9 fraction (Rvb=34+/- 4)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID679794	TP_TRANSPORTER: Northern blot in vitro, nonparenchymal ral liver epithelial cells	1996	Biochemical pharmacology, Jun-14, Volume: 51, Issue:11	P-glycoprotein induction in rat liver epithelial cells in response to acute 3-methylcholanthrene treatment.
AID1687886	Genotoxicity in human HepG2 assessed as survival at 100 ug/ml measured after 24 hrs by micronucleus test (Rvb = 100%)	2020	European journal of medicinal chemistry, Jan-15, Volume: 186	Novel nitroimidazole derivatives evaluated for their trypanocidal, cytotoxic, and genotoxic activities.
AID679999	TP_TRANSPORTER: transepithelial transport (basal to apical) in mdr1a-expressing LLC-PK1 cell	1998	Archives of biochemistry and biophysics, Feb-15, Volume: 350, Issue:2	Human MDR1 and mouse mdr1a P-glycoprotein alter the cellular retention and disposition of erythromycin, but not of retinoic acid or benzo(a)pyrene.
AID1201521	Mutagenicity in Salmonella typhimurium TA100 at 2.5 mM after 1 hr by Ames test in presence of S9 fraction	2015	European journal of medicinal chemistry, May-05, Volume: 95	Discovery of new thienopyrimidinone derivatives displaying antimalarial properties toward both erythrocytic and hepatic stages of Plasmodium.
AID252220	Average fold change in expression of CYP1A1 after treatment with compound of concentration 0.1 mM in human MCF-7 cells	2005	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 15, Issue:5	Effects of suberoylanilide hydroxamic acid and trichostatin A on induction of cytochrome P450 enzymes and benzo[a]pyrene DNA adduct formation in human cells.
AID252218	Average fold change in expression of CYP1A1 after treatment with compound of concentration 1 mM in human MCF-7 cells	2005	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 15, Issue:5	Effects of suberoylanilide hydroxamic acid and trichostatin A on induction of cytochrome P450 enzymes and benzo[a]pyrene DNA adduct formation in human cells.
AID252223	Average fold change in expression of CYP1A1 after treatment with compound of concentration 0.01 mM in human MCF-7 cells	2005	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 15, Issue:5	Effects of suberoylanilide hydroxamic acid and trichostatin A on induction of cytochrome P450 enzymes and benzo[a]pyrene DNA adduct formation in human cells.
AID252217	Average fold change in expression of CYP1B1 at 1 mM after co-treatment with compound and SAHA in human MCF-7 cells	2005	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 15, Issue:5	Effects of suberoylanilide hydroxamic acid and trichostatin A on induction of cytochrome P450 enzymes and benzo[a]pyrene DNA adduct formation in human cells.
AID1201520	Mutagenicity in Salmonella typhimurium TA97A at 2.5 mM after 1 hr by Ames test in presence of S9 fraction	2015	European journal of medicinal chemistry, May-05, Volume: 95	Discovery of new thienopyrimidinone derivatives displaying antimalarial properties toward both erythrocytic and hepatic stages of Plasmodium.
AID250199	Mean B[a]P DNA binding at 4 uM after co-treatment with compound and TSA (2 uM) in human MCF-7 cells	2005	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 15, Issue:5	Effects of suberoylanilide hydroxamic acid and trichostatin A on induction of cytochrome P450 enzymes and benzo[a]pyrene DNA adduct formation in human cells.
AID1687884	Genotoxicity in human HepG2 assessed as mitotic index at 100 ug/ml measured after 24 hrs by micronucleus test (Rvb = 61 to 108 No_unit)	2020	European journal of medicinal chemistry, Jan-15, Volume: 186	Novel nitroimidazole derivatives evaluated for their trypanocidal, cytotoxic, and genotoxic activities.
AID1320168	Cytotoxicity against CHL cells assessed as number of cells with numerical aberrations at 20 ug/ml preincubated for 6 hrs followed by 18 hrs incubation in fresh medium in presence of S9 fraction by Giemsa staining-based microscopic analysis relative to con	2016	Bioorganic & medicinal chemistry, 11-01, Volume: 24, Issue:21	Phosphonate-based irreversible inhibitors of human γ-glutamyl transpeptidase (GGT). GGsTop is a non-toxic and highly selective inhibitor with critical electrostatic interaction with an active-site residue Lys562 for enhanced inhibitory activity.
AID250212	Mean B[a]P DNA binding at 4 uM after co-treatment with compound and SAHA (2 uM) in human MCF-7 cells	2005	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 15, Issue:5	Effects of suberoylanilide hydroxamic acid and trichostatin A on induction of cytochrome P450 enzymes and benzo[a]pyrene DNA adduct formation in human cells.
AID189495	Rate of 3-hydroxylation by lung microsomes in rats induced with 3-MC; Rates are expressed as pmol of product per 30 min per mg of protein	1980	Journal of medicinal chemistry, Aug, Volume: 23, Issue:8	Metabolism of 6-substituted benzo[a]pyrene derivatives: O-dealkylation and regiospecificity in aromatic hydroxylation.
AID252225	Average fold change in expression of CYP1B1 after treatment with compound of concentration 0.01 mM in human MCF-7 cells	2005	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 15, Issue:5	Effects of suberoylanilide hydroxamic acid and trichostatin A on induction of cytochrome P450 enzymes and benzo[a]pyrene DNA adduct formation in human cells.
AID1687885	Genotoxicity in human HepG2 assessed as number of micronucleated cells at 100 ug/ml measured after 24 hrs by micronucleus test (Rvb = 14 to 18 No_unit)	2020	European journal of medicinal chemistry, Jan-15, Volume: 186	Novel nitroimidazole derivatives evaluated for their trypanocidal, cytotoxic, and genotoxic activities.
AID1241896	Genotoxicity in Salmonella typhimurium TA98 assessed as induction of revertant colonies at 2 ug/plate in presence of S9 mix by Ames test relative untreated control	2015	European journal of medicinal chemistry, Aug-28, Volume: 101	Novel benzidine and diaminofluorene prolinamide derivatives as potent hepatitis C virus NS5A inhibitors.
AID189502	Rate of hydroxylation by liver microsomes in rats induced with PB; Rates are expressed as pmol of product per 30 min per mg of protein	1980	Journal of medicinal chemistry, Aug, Volume: 23, Issue:8	Metabolism of 6-substituted benzo[a]pyrene derivatives: O-dealkylation and regiospecificity in aromatic hydroxylation.
AID465481	Mutagenic activity in Salmonella Typhimurium TA97a assessed as increase in number of revertants at 0.5 ug/plate by Ames test presence of S9 fraction (Rvb=154+/-18)	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745845	Primary qHTS for Inhibitors of ATXN expression
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635	Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1159607	Screen for inhibitors of RMI FANCM (MM2) intereaction	2016	Journal of biomolecular screening, Jul, Volume: 21, Issue:6	A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
AID1159550	Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening	2015	Nature cell biology, Nov, Volume: 17, Issue:11	6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1789 (25.77)	18.7374
1990's	1303 (18.77)	18.2507
2000's	1519 (21.88)	29.6817
2010's	1729 (24.91)	24.3611
2020's	602 (8.67)	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	17 (0.23%)	5.53%
Reviews	194 (2.65%)	6.00%
Case Studies	2 (0.03%)	4.05%
Observational	1 (0.01%)	0.25%
Other	7,097 (97.07%)	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.	3.23	6	0	C-nitro compound; monochlorobenzenes	allergen; epitope; sensitiser
ethylene dichloride ethylene dichloride: RN given refers to 1,2-isomer; structure given in first source. 1,2-dichloroethane : A member of the class of chloroethanes substituted by two chloro groups at positions 1 and 2.	2.52	2	0	chloroethanes	hepatotoxic agent; mutagen; non-polar solvent
1,2,4-trichlorobenzene 1,2,4-trichlorobenzene : A trichlorobenzene with chloro substituents at positions 1, 2 and 4.	2.45	2	0	trichlorobenzene
ethylene chlorohydrin Ethylene Chlorohydrin: Used as a solvent, in the manufacture of insecticides, and for treating sweet potatoes before planting. May cause nausea, vomiting, pains in head and chest, stupefaction. Irritates mucous membranes and causes kidney and liver degeneration.. chloroethanol : An organochlorine compound that is ethanol substituted by at least one chloro group.	2.36	2	0	chloroethanol	xenobiotic metabolite
protocatechuic acid protocatechuic acid: RN given refers to parent cpd; structure. 3,4-dihydroxybenzoic acid : A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4.	2.25	1	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
aminolevulinic acid Aminolevulinic Acid: A compound produced from succinyl-CoA and GLYCINE as an intermediate in heme synthesis. It is used as a PHOTOCHEMOTHERAPY for actinic KERATOSIS.. 5-aminolevulinic acid : The simplest delta-amino acid in which the hydrogens at the gamma position are replaced by an oxo group. It is metabolised to protoporphyrin IX, a photoactive compound which accumulates in the skin. Used (in the form of the hydrochloride salt)in combination with blue light illumination for the treatment of minimally to moderately thick actinic keratosis of the face or scalp.	2.11	1	0	4-oxo monocarboxylic acid; amino acid zwitterion; delta-amino acid	antineoplastic agent; dermatologic drug; Escherichia coli metabolite; human metabolite; mouse metabolite; photosensitizing agent; plant metabolite; prodrug; Saccharomyces cerevisiae metabolite
5-hydroxytryptophan 5-Hydroxytryptophan: The immediate precursor in the biosynthesis of SEROTONIN from tryptophan. It is used as an antiepileptic and antidepressant.. 5-hydroxytryptophan : A tryptophan derivative that is tryptophan substituted by a hydroxy group at position 5.	1.96	1	0	hydroxytryptophan	human metabolite; neurotransmitter
ethylene glycol Ethylene Glycol: A colorless, odorless, viscous dihydroxy alcohol. It has a sweet taste, but is poisonous if ingested. Ethylene glycol is the most important glycol commercially available and is manufactured on a large scale in the United States. It is used as an antifreeze and coolant, in hydraulic fluids, and in the manufacture of low-freezing dynamites and resins.. ethanediol : Any diol that is ethane or substituted ethane carrying two hydroxy groups.. ethylene glycol : A 1,2-glycol compound produced via reaction of ethylene oxide with water.	2.52	2	0	ethanediol; glycol	metabolite; mouse metabolite; solvent; toxin
acetic acid Acetic Acid: Product of the oxidation of ethanol and of the destructive distillation of wood. It is used locally, occasionally internally, as a counterirritant and also as a reagent. (Stedman, 26th ed). acetic acid : A simple monocarboxylic acid containing two carbons.	2.42	2	0	monocarboxylic acid	antimicrobial food preservative; Daphnia magna metabolite; food acidity regulator; protic solvent
acetaldehyde Acetaldehyde: A colorless, flammable liquid used in the manufacture of acetic acid, perfumes, and flavors. It is also an intermediate in the metabolism of alcohol. It has a general narcotic action and also causes irritation of mucous membranes. Large doses may cause death from respiratory paralysis.. acetaldehyde : The aldehyde formed from acetic acid by reduction of the carboxy group. It is the most abundant carcinogen in tobacco smoke.. aldehyde : A compound RC(=O)H, in which a carbonyl group is bonded to one hydrogen atom and to one R group.. acetyl group : A group, formally derived from acetic acid by dehydroxylation, which is fundamental to the biochemistry of all forms of life. When bound to coenzyme A, it is central to the metabolism of carbohydrates and fats.	2.92	4	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
acetamide acetimidic acid : A carboximidic acid that is acetic acid in which the carbonyl oxygen is replaced by an imino group.	2.38	2	0	acetamides; carboximidic acid; monocarboxylic acid amide; N-acylammonia
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	3.99	14	0	ketone body; methyl ketone; propanones; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; human metabolite; polar aprotic solvent
adenine [no description available]	3.96	13	0	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
allantoin [no description available]	1.97	1	0	imidazolidine-2,4-dione; ureas	Escherichia coli metabolite; human metabolite; Saccharomyces cerevisiae metabolite; vulnerary
ammonium hydroxide azane : Saturated acyclic nitrogen hydrides having the general formula NnHn+2.	2.4	2	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
quinacrine Quinacrine: An acridine derivative formerly widely used as an antimalarial but superseded by chloroquine in recent years. It has also been used as an anthelmintic and in the treatment of giardiasis and malignant effusions. It is used in cell biological experiments as an inhibitor of phospholipase A2.. quinacrine : A member of the class of acridines that is acridine substituted by a chloro group at position 6, a methoxy group at position 2 and a [5-(diethylamino)pentan-2-yl]nitrilo group at position 9.	1.96	1	0	acridines; aromatic ether; organochlorine compound; tertiary amino compound	antimalarial; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor
benzene [no description available]	12.27	42	0	aromatic annulene; benzenes; volatile organic compound	carcinogenic agent; environmental contaminant; non-polar solvent
benzoic acid Benzoic Acid: A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid.. benzoic acid : A compound comprising a benzene ring core carrying a carboxylic acid substituent.. aromatic carboxylic acid : Any carboxylic acid in which the carboxy group is directly bonded to an aromatic ring.	1.97	1	0	benzoic acids	algal metabolite; antimicrobial food preservative; drug allergen; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 3.1.1.3 (triacylglycerol lipase) inhibitor; human xenobiotic metabolite; plant metabolite
betaine glycine betaine : The amino acid betaine derived from glycine.	4.9	1	1	amino-acid betaine; glycine derivative	fundamental metabolite
bromide Bromides: Salts of hydrobromic acid, HBr, with the bromine atom in the 1- oxidation state. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	2.05	1	0	halide anion; monoatomic bromine
1-butanol 1-Butanol: A four carbon linear hydrocarbon that has a hydroxy group at position 1.. butan-1-ol : A primary alcohol that is butane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It it produced in small amounts in humans by the gut microbes.	3.41	7	0	alkyl alcohol; primary alcohol; short-chain primary fatty alcohol	human metabolite; mouse metabolite; protic solvent
butyric acid Butyric Acid: A four carbon acid, CH3CH2CH2COOH, with an unpleasant odor that occurs in butter and animal fat as the glycerol ester.. butyrate : A short-chain fatty acid anion that is the conjugate base of butyric acid, obtained by deprotonation of the carboxy group.. butyric acid : A straight-chain saturated fatty acid that is butane in which one of the terminal methyl groups has been oxidised to a carboxy group.	2.74	3	0	fatty acid 4:0; straight-chain saturated fatty acid	human urinary metabolite; Mycoplasma genitalium metabolite
carbamates [no description available]	2.31	1	0	amino-acid anion
carbon monoxide Carbon Monoxide: Carbon monoxide (CO). A poisonous colorless, odorless, tasteless gas. It combines with hemoglobin to form carboxyhemoglobin, which has no oxygen carrying capacity. The resultant oxygen deprivation causes headache, dizziness, decreased pulse and respiratory rates, unconsciousness, and death. (From Merck Index, 11th ed). carbon monoxide : A one-carbon compound in which the carbon is joined only to a single oxygen. It is a colourless, odourless, tasteless, toxic gas.	5.68	15	0	carbon oxide; gas molecular entity; one-carbon compound	biomarker; EC 1.9.3.1 (cytochrome c oxidase) inhibitor; human metabolite; ligand; metabolite; mitochondrial respiratory-chain inhibitor; mouse metabolite; neurotoxin; neurotransmitter; P450 inhibitor; probe; signalling molecule; vasodilator agent
catechol [no description available]	2.66	3	0	catechols	allelochemical; genotoxin; plant metabolite
methane Methane: The simplest saturated hydrocarbon. It is a colorless, flammable gas, slightly soluble in water. It is one of the chief constituents of natural gas and is formed in the decomposition of organic matter. (Grant & Hackh's Chemical Dictionary, 5th ed). methane : A one-carbon compound in which the carbon is attached by single bonds to four hydrogen atoms. It is a colourless, odourless, non-toxic but flammable gas (b.p. -161degreeC).	4.13	14	0	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
chlordecone [no description available]	2.37	2	0	cyclic ketone; organochlorine compound	insecticide; persistent organic pollutant
choline [no description available]	4.9	1	1	cholines	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter; nutrient; plant metabolite; Saccharomyces cerevisiae metabolite
citric acid, anhydrous Citric Acid: A key intermediate in metabolism. It is an acid compound found in citrus fruits. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability.. citric acid : A tricarboxylic acid that is propane-1,2,3-tricarboxylic acid bearing a hydroxy substituent at position 2. It is an important metabolite in the pathway of all aerobic organisms.	2.73	3	0	tricarboxylic acid	antimicrobial agent; chelator; food acidity regulator; fundamental metabolite
chlorine chloride : A halide anion formed when chlorine picks up an electron to form an an anion.	2.67	3	0	halide anion; monoatomic chlorine	cofactor; Escherichia coli metabolite; human metabolite
hydrochloric acid Hydrochloric Acid: A strong corrosive acid that is commonly used as a laboratory reagent. It is formed by dissolving hydrogen chloride in water. GASTRIC ACID is the hydrochloric acid component of GASTRIC JUICE.. hydrogen chloride : A mononuclear parent hydride consisting of covalently bonded hydrogen and chlorine atoms.	2.08	1	0	chlorine molecular entity; gas molecular entity; hydrogen halide; mononuclear parent hydride	mouse metabolite
coumarin 2H-chromen-2-one: coumarin derivative	7.92	4	0	coumarins	fluorescent dye; human metabolite; plant metabolite
4-vinylguaiacol 2-methoxy-4-vinylphenol: a germination inhibitor; also an odorant in green tea; structure in first source. 2-methoxy-4-vinylphenol : A member of the class of phenols that is guaiacol in which the hydrogen para- to the hydroxy group is replaced by a vinyl group.	2.05	1	0	phenols	flavouring agent; pheromone; plant metabolite
2-cresol 2-cresol: RN given refers to parent cpd. o-cresol : A cresol that is phenol substituted by a methyl group at position 2. It is a minor urinary metabolite of toluene.	2.67	3	0	cresol	human xenobiotic metabolite
salicylic acid Scalp: The outer covering of the calvaria. It is composed of several layers: SKIN; subcutaneous connective tissue; the occipitofrontal muscle which includes the tendinous galea aponeurotica; loose connective tissue; and the pericranium (the PERIOSTEUM of the SKULL).	2.51	2	0	monohydroxybenzoic acid	algal metabolite; antifungal agent; antiinfective agent; EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor; keratolytic drug; plant hormone; plant metabolite
octane Octanes: Eight-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives.. octane : A straight chain alkane composed of 8 carbon atoms.	2.04	1	0	alkane	xenobiotic
gallic acid gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.	2.94	4	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
octanoic acid octanoic acid: RN given refers to parent cpd; structure in Merck Index, 9th ed, #1764. octanoic acid : A straight-chain saturated fatty acid that is heptane in which one of the hydrogens of a terminal methyl group has been replaced by a carboxy group. Octanoic acid is also known as caprylic acid.	2.41	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	antibacterial agent; Escherichia coli metabolite; human metabolite
hydrogen sulfide Hydrogen Sulfide: A flammable, poisonous gas with a characteristic odor of rotten eggs. It is used in the manufacture of chemicals, in metallurgy, and as an analytical reagent. (From Merck Index, 11th ed). hydrogen sulfide : A sulfur hydride consisting of a single sulfur atom bonded to two hydrogen atoms. A highly poisonous, flammable gas with a characteristic odour of rotten eggs, it is often produced by bacterial decomposition of organic matter in the absence of oxygen.. thiol : An organosulfur compound in which a thiol group, -SH, is attached to a carbon atom of any aliphatic or aromatic moiety.	1.99	1	0	gas molecular entity; hydracid; mononuclear parent hydride; sulfur hydride	Escherichia coli metabolite; genotoxin; metabolite; signalling molecule; toxin; vasodilator agent
nornicotine nornicotine: agricultural or horticultural insecticide; RN given refers to (+-)-isomer; structure	1.96	1	0
guaiacol Guaiacol: An agent thought to have disinfectant properties and used as an expectorant. (From Martindale, The Extra Pharmacopoeia, 30th ed, p747). methylcatechol : Any member of the class of catechols carrying one or more methyl substituents.. guaiacol : A monomethoxybenzene that consists of phenol with a methoxy substituent at the ortho position.	8.88	12	0	guaiacols	disinfectant; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; expectorant; plant metabolite
3,4-dihydroxyphenylacetic acid 3,4-Dihydroxyphenylacetic Acid: A deaminated metabolite of LEVODOPA.. (3,4-dihydroxyphenyl)acetic acid : A dihydroxyphenylacetic acid having the two hydroxy substituents located at the 3- and 4-positions. It is a metabolite of dopamine.. dihydroxyphenylacetic acid : A dihydroxy monocarboxylic acid consisting of phenylacetic acid having two phenolic hydroxy substituents.	2.44	2	0	catechols; dihydroxyphenylacetic acid	human metabolite
aminocaproic acid Aminocaproic Acid: An antifibrinolytic agent that acts by inhibiting plasminogen activators which have fibrinolytic properties.. 6-aminohexanoic acid : An epsilon-amino acid comprising hexanoic acid carrying an amino substituent at position C-6. Used to control postoperative bleeding, and to treat overdose effects of the thrombolytic agents streptokinase and tissue plasminogen activator.	7.1	1	0	amino acid zwitterion; epsilon-amino acid; omega-amino fatty acid	antifibrinolytic drug; hematologic agent; metabolite
dibenzofuran Dibenzofurans: Compounds that include the structure of dibenzofuran.. dibenzofurans : Any organic heterotricyclic compound based on a dibenzofuran skeleton and its substituted derivatives thereof.. dibenzofuran : A mancude organic heterotricyclic parent that consists of a furan ring flanked by two benzene rings ortho-fused across the 2,3- and 4,5-positions.	5.4	3	1	dibenzofurans; mancude organic heterotricyclic parent; polycyclic heteroarene	xenobiotic
cytosine [no description available]	4.7	9	0	aminopyrimidine; pyrimidine nucleobase; pyrimidone	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
lactic acid Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.	3.95	12	0	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
dimethyl sulfoxide Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.	12.42	37	1	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
ethanolamine [no description available]	3.09	1	0	ethanolamines; primary alcohol; primary amine	Escherichia coli metabolite; human metabolite; mouse metabolite
formaldehyde paraform: polymerized formaldehyde; RN given refers to parent cpd; used in root canal therapy	11.14	17	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
hexachlorocyclohexane Lindane: An organochlorine insecticide made up of greater than 99% gamma-Hexachlorocyclohexane. It has been used as a pediculicide and scabicide, and shown to cause cancer.. beta-hexachlorocyclohexane : The beta-isomer of hexachlorocyclohexane.	2.39	2	0	chlorocyclohexane
glycine [no description available]	2.42	2	0	alpha-amino acid; amino acid zwitterion; proteinogenic amino acid; serine family amino acid	EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor; fundamental metabolite; hepatoprotective agent; micronutrient; neurotransmitter; NMDA receptor agonist; nutraceutical
glycerol Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.	2.06	1	0	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
hydrogen carbonate Bicarbonates: Inorganic salts that contain the -HCO3 radical. They are an important factor in determining the pH of the blood and the concentration of bicarbonate ions is regulated by the kidney. Levels in the blood are an index of the alkali reserve or buffering capacity.. hydrogencarbonate : The carbon oxoanion resulting from the removal of a proton from carbonic acid.	1.97	1	0	carbon oxoanion	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
histamine [no description available]	3.98	4	0	aralkylamino compound; imidazoles	human metabolite; mouse metabolite; neurotransmitter
hydrogen Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.	2.69	2	0	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
imidazole imidazole: RN given refers to parent cpd. 1H-imidazole : An imidazole tautomer which has the migrating hydrogen at position 1.	2.88	4	0	imidazole
indole [no description available]	1.99	1	0	indole; polycyclic heteroarene	Escherichia coli metabolite
iodine Iodine: A nonmetallic element of the halogen group that is represented by the atomic symbol I, atomic number 53, and atomic weight of 126.90. It is a nutritionally essential element, especially important in thyroid hormone synthesis. In solution, it has anti-infective properties and is used topically.. diiodine : Molecule comprising two covalently bonded iodine atoms with overall zero charge..	2.13	1	0	diatomic iodine	nutrient
methanol Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.	9.75	30	0	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
inositol Inositol: An isomer of glucose that has traditionally been considered to be a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in man. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1379) Inositol phospholipids are important in signal transduction.. inositol : Any cyclohexane-1,2,3,4,5,6-hexol.. 1D-chiro-inositol : Belonging to the inositol family of compounds, D-chiro-inositol (DCI) is an isomer of glucose. It is an important secondary messenger in insulin signal transduction.. muco-inositol : An inositol that is cyclohexane-1,2,3,4,5,6-hexol having a (1R,2R,3r,4R,5S,6r)-configuration.	4.77	7	0	cyclitol; hexol
melatonin [no description available]	6.57	13	1	acetamides; tryptamines	anticonvulsant; central nervous system depressant; geroprotector; hormone; human metabolite; immunological adjuvant; mouse metabolite; radical scavenger
croton oil [no description available]	3.98	5	0	N-acyl-hexosamine
naphthalene [no description available]	6.73	43	0	naphthalenes; ortho-fused bicyclic arene	apoptosis inhibitor; carcinogenic agent; environmental contaminant; mouse metabolite; plant metabolite; volatile oil component
nickel Nickel: A trace element with the atomic symbol Ni, atomic number 28, and atomic weight 58.69. It is a cofactor of the enzyme UREASE.. nickel ion : A nickel atom having a net electric charge.. nickel atom : Chemical element (nickel group element atom) with atomic number 28.	9.06	15	0	metal allergen; nickel group element atom	epitope; micronutrient
niacinamide nicotinamide : A pyridinecarboxamide that is pyridine in which the hydrogen at position 3 is replaced by a carboxamide group.	3.21	6	0	pyridine alkaloid; pyridinecarboxamide; vitamin B3	anti-inflammatory agent; antioxidant; cofactor; EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; Escherichia coli metabolite; geroprotector; human urinary metabolite; metabolite; mouse metabolite; neuroprotective agent; Saccharomyces cerevisiae metabolite; Sir2 inhibitor
niacin Niacin: A water-soluble vitamin of the B complex occurring in various animal and plant tissues. It is required by the body for the formation of coenzymes NAD and NADP. It has PELLAGRA-curative, vasodilating, and antilipemic properties.. vitamin B3 : Any member of a group of vitamers that belong to the chemical structural class called pyridines that exhibit biological activity against vitamin B3 deficiency. Vitamin B3 deficiency causes a condition known as pellagra whose symptoms include depression, dermatitis and diarrhea. The vitamers include nicotinic acid and nicotinamide (and their ionized and salt forms).. nicotinic acid : A pyridinemonocarboxylic acid that is pyridine in which the hydrogen at position 3 is replaced by a carboxy group.	2.34	2	0	pyridine alkaloid; pyridinemonocarboxylic acid; vitamin B3	antidote; antilipemic drug; EC 3.5.1.19 (nicotinamidase) inhibitor; Escherichia coli metabolite; human urinary metabolite; metabolite; mouse metabolite; plant metabolite; vasodilator agent
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	5.27	16	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)	4.89	11	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species	human metabolite
n,n-dimethylaniline N,N-dimethylaniline: RN given refers to parent cpd; structure. dimethylaniline : A methylaniline carrying at least two methyl groups.. N,N-dimethylaniline : A tertiary amine that is aniline in which the amino hydrogens are replaced by two methyl groups.	1.96	1	0	dimethylaniline; tertiary amine
1-octanol 1-Octanol: A colorless, slightly viscous liquid used as a defoaming or wetting agent. It is also used as a solvent for protective coatings, waxes, and oils, and as a raw material for plasticizers. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). octan-1-ol : An octanol carrying the hydroxy group at position 1.	2.67	3	0	octanol; primary alcohol	antifungal agent; bacterial metabolite; fuel additive; kairomone; plant metabolite
hydroxide ion [no description available]	2	1	0	oxygen hydride	mouse metabolite
orotic acid Orotic Acid: An intermediate product in PYRIMIDINE synthesis which plays a role in chemical conversions between DIHYDROFOLATE and TETRAHYDROFOLATE.. orotic acid : A pyrimidinemonocarboxylic acid that is uracil bearing a carboxy substituent at position C-6.	2.4	2	0	pyrimidinemonocarboxylic acid	Escherichia coli metabolite; metabolite; mouse metabolite
oxalic acid Oxalic Acid: A strong dicarboxylic acid occurring in many plants and vegetables. It is produced in the body by metabolism of glyoxylic acid or ascorbic acid. It is not metabolized but excreted in the urine. It is used as an analytical reagent and general reducing agent.. oxalic acid : An alpha,omega-dicarboxylic acid that is ethane substituted by carboxyl groups at positions 1 and 2.	2.11	1	0	alpha,omega-dicarboxylic acid	algal metabolite; human metabolite; plant metabolite
4-aminobenzoic acid 4-Aminobenzoic Acid: An aminobenzoic acid isomer that combines with pteridine and GLUTAMIC ACID to form FOLIC ACID. The fact that 4-aminobenzoic acid absorbs light throughout the UVB range has also resulted in its use as an ingredient in SUNSCREENS.. 4-ammoniobenzoate : A zwitterion obtained by transfer of a proton from the carboxy to the amino group of 4-aminobenzoic acid.. 4-aminobenzoic acid : An aminobenzoic acid in which the amino group is para to the carboxy group.	2.41	2	0	aminobenzoic acid; aromatic amino-acid zwitterion	allergen; Escherichia coli metabolite; plant metabolite
4-nitrophenol 4-nitrophenol: RN given refers to parent cpd. mononitrophenol : A nitrophenol that is phenol carrying a single nitro substituent at unspecified position.. 4-nitrophenol : A member of the class of 4-nitrophenols that is phenol in which the hydrogen that is para to the hydroxy group has been replaced by a nitro group.	2.92	4	0	4-nitrophenols	human xenobiotic metabolite; mouse metabolite
pentachlorophenol PENTA: structure given in first source	3.95	13	0	aromatic fungicide; chlorophenol; organochlorine pesticide; pentachlorobenzenes	human xenobiotic metabolite
phenanthrene phenanthrene : A polycyclic aromatic hydrocarbon composed of three fused benzene rings which takes its name from the two terms 'phenyl' and 'anthracene.'	9.62	111	0	ortho-fused polycyclic arene; ortho-fused tricyclic hydrocarbon; phenanthrenes	environmental contaminant; mouse metabolite
phenol [no description available]	3.61	9	0	phenols	antiseptic drug; disinfectant; human xenobiotic metabolite; mouse metabolite
phosphorylcholine Phosphorylcholine: Calcium and magnesium salts used therapeutically in hepatobiliary dysfunction.. phosphocholine : The phosphate of choline; and the parent compound of the phosphocholine family.	2.39	2	0	phosphocholines	allergen; epitope; hapten; human metabolite; mouse metabolite
phosphorylethanolamine phosphorylethanolamine: RN given refers to parent cpd; structure. O-phosphoethanolamine : The ethanolamine mono-ester of phosphoric acid, and a metabolite of phospholipid metabolism. This phosphomonoester shows strong structural similarity to the inhibitory neurotransmitter GABA, and is decreased in post-mortem Alzheimer's disease brain.	1.98	1	0	phosphoethanolamine; primary amino compound	algal metabolite; human metabolite; mouse metabolite
phthalic acid phthalic acid: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7178. phthalic acid : A benzenedicarboxylic acid cosisting of two carboxy groups at ortho positions.	3.17	5	0	benzenedicarboxylic acid	human xenobiotic metabolite
propylene glycol Propylene Glycol: A clear, colorless, viscous organic solvent and diluent used in pharmaceutical preparations.. propane-1,2-diol : The simplest member of the class of propane-1,2-diols, consisting of propane in which a hydrogen at position 1 and a hydrogen at position 2 are substituted by hydroxy groups. A colourless, viscous, hygroscopic, low-melting (-59degreeC) and high-boiling (188degreeC) liquid with low toxicity, it is used as a solvent, emulsifying agent, and antifreeze.	2.06	1	0	glycol; propane-1,2-diols	allergen; human xenobiotic metabolite; mouse metabolite; protic solvent
1-propanol 1-Propanol: A colorless liquid made by oxidation of aliphatic hydrocarbons that is used as a solvent and chemical intermediate.. propan-1-ol : The parent member of the class of propan-1-ols that is propane in which a hydrogen of one of the methyl groups is replaced by a hydroxy group.	2.38	2	0	propan-1-ols; short-chain primary fatty alcohol	metabolite; protic solvent
propionic acid propionic acid : A short-chain saturated fatty acid comprising ethane attached to the carbon of a carboxy group.	2.02	1	0	saturated fatty acid; short-chain fatty acid	antifungal drug
putrescine [no description available]	2.66	3	0	alkane-alpha,omega-diamine	antioxidant; fundamental metabolite
pyrazole 1H-pyrazole : The 1H-tautomer of pyrazole.	1.96	1	0	pyrazole
pyridine azine : An organonitrogen compound of general structure RCH=N-N=CHR or RR'C=N-N=CRR'.	2.68	3	0	azaarene; mancude organic heteromonocyclic parent; monocyclic heteroarene; pyridines	environmental contaminant; NMR chemical shift reference compound
pyrogallol benzenetriol : A triol in which three hydroxy groups are substituted onto a benzene ring.	2.88	4	0	benzenetriol; phenolic donor	plant metabolite
dimethyl sulfide dimethyl sulfide: structure. dimethyl sulfide : A methyl sulfide in which the sulfur atom is substituted by two methyl groups. It is produced naturally by some marine algae.. methyl sulfide : Any aliphatic sulfide in which at least one of the organyl groups attached to the sulfur is a methyl group.	2.04	1	0	aliphatic sulfide	algal metabolite; bacterial xenobiotic metabolite; EC 3.5.1.4 (amidase) inhibitor; Escherichia coli metabolite; marine metabolite
dithionite Dithionite: Dithionite. The dithionous acid ion and its salts.	1.96	1	0	sulfur oxide; sulfur oxoanion
selenic acid Selenic Acid: A strong dibasic acid with the molecular formula H2SeO4. Included under this heading is the acid form, and inorganic salts of dihydrogen selenium tetraoxide.	1.97	1	0	selenium oxoacid
selenious acid Selenious Acid: A selenium compound with the molecular formula H2SO3. It used as a source of SELENIUM, especially for patients that develop selenium deficiency following prolonged PARENTERAL NUTRITION.	2.37	2	0	selenium oxoacid
sulfites Sulfites: Inorganic salts of sulfurous acid.. sulfites : Any sulfurous acid derivative that is a salt or an ester of sulfurous acid.. organosulfonate oxoanion : An organic anion obtained by deprotonation of the sufonate group(s) of any organosulfonic acid.. sulfite : A sulfur oxoanion that is the conjugate base of hydrogen sulfite (H2SO3).	3.69	10	0	divalent inorganic anion; sulfur oxide; sulfur oxoanion
spermidine [no description available]	2.66	3	0	polyazaalkane; triamine	autophagy inducer; fundamental metabolite; geroprotector
spermine [no description available]	1.96	1	0	polyazaalkane; tetramine	antioxidant; fundamental metabolite; immunosuppressive agent
succinic acid Succinic Acid: A water-soluble, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. (Hawley's Condensed Chemical Dictionary, 12th ed, p1099; McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed, p1851). succinic acid : An alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle.	2.25	1	0	alpha,omega-dicarboxylic acid; C4-dicarboxylic acid	anti-ulcer drug; fundamental metabolite; micronutrient; nutraceutical; radiation protective agent
sulfuric acid sulfuric acid : A sulfur oxoacid that consists of two oxo and two hydroxy groups joined covalently to a central sulfur atom.	3.49	2	0	sulfur oxoacid	catalyst
sulfur dioxide Sulfur Dioxide: A highly toxic, colorless, nonflammable gas. It is used as a pharmaceutical aid and antioxidant. It is also an environmental air pollutant.	5.49	21	0	sulfur oxide	Escherichia coli metabolite; food bleaching agent; refrigerant
taurine [no description available]	2.38	2	0	amino sulfonic acid; zwitterion	antioxidant; Escherichia coli metabolite; glycine receptor agonist; human metabolite; mouse metabolite; nutrient; radical scavenger; Saccharomyces cerevisiae metabolite
thiamine thiamine(1+) : A primary alcohol that is 1,3-thiazol-3-ium substituted by (4-amino-2-methylpyrimidin-5-yl)methyl, methyl and 2-hydroxyethyl groups at positions 3, 4 and 5, respectively.	2.04	1	0	primary alcohol; vitamin B1	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
toluene methylbenzene : Any alkylbenzene that is benzene substituted with one or more methyl groups.	4.31	19	0	methylbenzene; toluenes; volatile organic compound	cholinergic antagonist; fuel additive; neurotoxin; non-polar solvent
uracil 2,4-dihydroxypyrimidine: a urinary biomarker for bipolar disorder	2.41	2	0	pyrimidine nucleobase; pyrimidone	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; prodrug; Saccharomyces cerevisiae metabolite
uric acid Uric Acid: An oxidation product, via XANTHINE OXIDASE, of oxypurines such as XANTHINE and HYPOXANTHINE. It is the final oxidation product of purine catabolism in humans and primates, whereas in most other mammals URATE OXIDASE further oxidizes it to ALLANTOIN.. uric acid : An oxopurine that is the final oxidation product of purine metabolism.. 6-hydroxy-1H-purine-2,8(7H,9H)-dione : A tautomer of uric acid having oxo groups at C-2 and C-8 and a hydroxy group at C-6.. 7,9-dihydro-1H-purine-2,6,8(3H)-trione : An oxopurine in which the purine ring is substituted by oxo groups at positions 2, 6, and 8.	2.35	2	0	uric acid	Escherichia coli metabolite; human metabolite; mouse metabolite
urea pseudourea: clinical use; structure. isourea : A carboximidic acid that is the imidic acid tautomer of urea, H2NC(=NH)OH, and its hydrocarbyl derivatives.	2.42	2	0	isourea; monocarboxylic acid amide; one-carbon compound	Daphnia magna metabolite; Escherichia coli metabolite; fertilizer; flour treatment agent; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
xanthine 7H-xanthine : An oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-7 is protonated.. 9H-xanthine : An oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-9 is protonated.	1.98	1	0	xanthine	Saccharomyces cerevisiae metabolite
isocitric acid isocitric acid: RN given refers to unlabeled parent cpd. isocitric acid : A tricarboxylic acid that is propan-1-ol with a hydrogen at each of the 3 carbon positions replaced by a carboxy group.	1.96	1	0	secondary alcohol; tricarboxylic acid	fundamental metabolite
menthol Menthol: A monoterpene cyclohexanol produced from mint oils.	7.49	2	0	p-menthane monoterpenoid; secondary alcohol	volatile oil component
1,10-phenanthroline 1,10-phenanthroline: RN given refers to parent cpd; inhibits Zn-dependent metalloproteinases	2.4	2	0	phenanthroline	EC 2.7.1.1 (hexokinase) inhibitor; EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor
1,2-dimethylhydrazine 1,2-Dimethylhydrazine: A DNA alkylating agent that has been shown to be a potent carcinogen and is widely used to induce colon tumors in experimental animals.. 1,2-dimethylhydrazine : A member of the class of hydrazines that is hydrazine in which one of the hydrogens attached to each nitrogen is replaced by a methyl group. A powerful DNA alkylating agent and carcinogen, it is used to induce colon cancer in laboratory rats and mice.	4.57	8	0	hydrazines	alkylating agent; carcinogenic agent
1-aminobenzotriazole [no description available]	2.03	1	0
1-anilino-8-naphthalenesulfonate 1-anilino-8-naphthalenesulfonate: RN given refers to parent cpd. 8-anilinonaphthalene-1-sulfonic acid : A naphthalenesulfonic acid that is naphthalene-1-sulfonic acid substituted by a phenylamino group at position 8.	3.01	4	0	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
2,2'-dipyridyl 2,2'-Dipyridyl: A reagent used for the determination of iron.. 2,2'-bipyridine : A bipyridine in which the two pyridine moieties are linked by a bond between positions C-2 and C-2'.	2.05	1	0	bipyridine	chelator; ferroptosis inhibitor
2,4-dichlorophenoxyacetic acid 2,4-Dichlorophenoxyacetic Acid: An herbicide with irritant effects on the eye and the gastrointestinal system.. 2,4-D : A chlorophenoxyacetic acid that is phenoxyacetic acid in which the ring hydrogens at postions 2 and 4 are substituted by chlorines.	3.49	2	0	chlorophenoxyacetic acid; dichlorobenzene	agrochemical; defoliant; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; environmental contaminant; phenoxy herbicide; synthetic auxin
2,4-dinitrophenol 2,4-Dinitrophenol: A toxic dye, chemically related to trinitrophenol (picric acid), used in biochemical studies of oxidative processes where it uncouples oxidative phosphorylation. It is also used as a metabolic stimulant. (Stedman, 26th ed). dinitrophenol : Members of the class of nitrophenol carrying two nitro substituents.. 2,4-dinitrophenol : A dinitrophenol having the nitro groups at the 2- and 4-positions.	2.45	2	0	dinitrophenol	allergen; antiseptic drug; bacterial xenobiotic metabolite; geroprotector; oxidative phosphorylation inhibitor
2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine: mutagen from fried ground beef; structure given in first source. PhIP : An imidazopyridine that is 1H--imidazo[4,5-b]pyridine which is substituted at positions 1, 2, and 6 by methyl, amino, and phenyl groups, respectively. It is the most abundant of the mutagenic heterocyclic amines found in cooked meat and fish.	9.25	38	1	imidazopyridine; primary amino compound	carcinogenic agent; mutagen
2-aminofluorene [no description available]	10.75	28	0
mercaptoethanol Mercaptoethanol: A water-soluble thiol derived from hydrogen sulfide and ethanol. It is used as a reducing agent for disulfide bonds and to protect sulfhydryl groups from oxidation.	1.96	1	0	alkanethiol; primary alcohol	geroprotector
3-aminobenzamide [no description available]	1.96	1	0	benzamides; substituted aniline	EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor
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.	10.69	257	0	ortho- and peri-fused polycyclic arene	aryl hydrocarbon receptor agonist; carcinogenic agent
homovanillic acid Homovanillic Acid: A 3-O-methyl ETHER of (3,4-dihydroxyphenyl)acetic acid.. homovanillate : A hydroxy monocarboxylic acid anion which is obtained by deprotonation of the carboxy group of homovanillic acid.. homovanillic acid : A monocarboxylic acid that is the 3-O-methyl ether of (3,4-dihydroxyphenyl)acetic acid. It is a catecholamine metabolite.	2.03	1	0	guaiacols; monocarboxylic acid	human metabolite; mouse metabolite
4-nonylphenol 4-nonylphenol: structure in first source; see also record for nonylphenol. 4-nonylphenol : A member of the class of phenols that is phenol which is para-substituted with a nonyl group.	2.73	3	0	phenols	environmental contaminant
phenytoin [no description available]	4.99	7	0	imidazolidine-2,4-dione	anticonvulsant; drug allergen; sodium channel blocker; teratogenic agent
5,8,11,14-eicosatetraynoic acid 5,8,11,14-Eicosatetraynoic Acid: A 20-carbon unsaturated fatty acid containing 4 alkyne bonds. It inhibits the enzymatic conversion of arachidonic acid to prostaglandins E(2) and F(2a).	1.97	1	0	long-chain fatty acid
ethylisopropylamiloride ethylisopropylamiloride: structure in first source. ethylisopropylamiloride : A member of the class of pyrazines that is amiloride in which the amino substitutent of the pyrazine ring that is adjacent to the chloro substituent has been substituted by an ethyl group and by an isopropyl group.	2.02	1	0	aromatic amine; guanidines; monocarboxylic acid amide; organochlorine compound; pyrazines; tertiary amino compound	anti-arrhythmia drug; neuroprotective agent; sodium channel blocker
hydroxyindoleacetic acid (5-hydroxyindol-3-yl)acetic acid : A member of the class of indole-3-acetic acids that is indole-3-acetic acid substituted by a hydroxy group at C-5.	2.05	1	0	indole-3-acetic acids	drug metabolite; human metabolite; mouse metabolite
phenanthridone phenanthridone: coal tar derivative; structure given in first source. phenanthridone : A member of the class of phenanthridines that is phenanthridine with an oxo substituent at position 6. A poly(ADP-ribose) polymerase (PARP) inhibitor, it has been shown to exhibit immunosuppressive activity.	1.96	1	0	lactam; phenanthridines	EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor; immunosuppressive agent; mutagen
5,11-dihydroindolo[3,2-b]carbazole-12-carboxaldehyde [no description available]	2.41	1	0	indolocarbazole
2,2'-azobis(2-amidinopropane) 2,2'-azobis(2-amidinopropane): water-soluble free-radical initiator	2.39	2	0	monoazo compound
acetaminophen Acetaminophen: Analgesic antipyretic derivative of acetanilide. It has weak anti-inflammatory properties and is used as a common analgesic, but may cause liver, blood cell, and kidney damage.. paracetamol : A member of the class of phenols that is 4-aminophenol in which one of the hydrogens attached to the amino group has been replaced by an acetyl group.	3.59	9	0	acetamides; phenols	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; cyclooxygenase 3 inhibitor; environmental contaminant; ferroptosis inducer; geroprotector; hepatotoxic agent; human blood serum metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
ag-1296 6,7-dimethoxy-3-phenylquinoxaline: ATP-competitive inhibitor of receptor kinase	2.11	1	0	quinoxaline derivative
am 580 Am 580: a selctive retinoic acid receptor (alpha) agonist; structure given in first source. 4-{[(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbonyl]amino}benzoic acid : An amidobenzoic acid obtained by formal condensation of the carboxy group of (5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)benzoic acid with the anilino group of 4-aminobenzoic acid. A selective RARalpha agonist.	2.05	1	0	amidobenzoic acid; tetralins	antineoplastic agent; retinoic acid receptor alpha/beta agonist
ametantrone ametantrone: RN given refers to parent cpd; structure	1.97	1	0
pimagedine pimagedine: diamine oxidase & nitric oxide synthase inhibitor; an advanced glycosylation end product inhibitor; used in the treatment of diabetic complications; structure. aminoguanidine : A one-carbon compound whose unique structure renders it capable of acting as a derivative of hydrazine, guanidine or formamide.	2.03	1	0	guanidines; one-carbon compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor; EC 1.4.3.4 (monoamine oxidase) inhibitor
p-aminohippuric acid p-Aminohippuric Acid: The glycine amide of 4-aminobenzoic acid. Its sodium salt is used as a diagnostic aid to measure effective renal plasma flow (ERPF) and excretory capacity.. p-aminohippurate : A hippurate that is the conjugate base of p-aminohippuric acid, arising from deprotonation of the carboxy group.. p-aminohippuric acid : An N-acylglycine that is the 4-amino derivative of hippuric acid; used as a diagnostic agent in the measurement of renal plasma flow.	3.36	7	0	N-acylglycine	Daphnia magna metabolite
theophylline [no description available]	1.96	1	0	dimethylxanthine	adenosine receptor antagonist; anti-asthmatic drug; anti-inflammatory agent; bronchodilator agent; drug metabolite; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; fungal metabolite; human blood serum metabolite; immunomodulator; muscle relaxant; vasodilator agent
amiodarone Amiodarone: An antianginal and class III antiarrhythmic drug. It increases the duration of ventricular and atrial muscle action by inhibiting POTASSIUM CHANNELS and VOLTAGE-GATED SODIUM CHANNELS. There is a resulting decrease in heart rate and in vascular resistance.. amiodarone : A member of the class of 1-benzofurans that is 1-benzofuran substituted by a butyl group at position 2 and a 4-[2-(diethylamino)ethoxy]-3,5-diiodobenzoyl group at position 3. It is a cardiovascular drug used for the treatment of cardiac dysrhythmias.	2.6	1	0	1-benzofurans; aromatic ketone; organoiodine compound; tertiary amino compound	cardiovascular drug
anthralin Anthralin: An anthracene derivative that disrupts MITOCHONDRIA function and structure and is used for the treatment of DERMATOSES, especially PSORIASIS. It may cause FOLLICULITIS.. anthralin : An anthracene compound derived by the substitution of -OH groups for hydrogen at C-1 and C-8, and with an oxo group at C-9.	2.89	4	0	anthracenes	antipsoriatic
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.	1.96	1	0	pyrazolone	antipyretic; cyclooxygenase 3 inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
acetovanillone apocynin : An aromatic ketone that is 1-phenylethanone substituted by a hydroxy group at position 4 and a methoxy group at position 3.	2.05	1	0	acetophenones; aromatic ketone; methyl ketone	antirheumatic drug; EC 1.6.3.1. [NAD(P)H oxidase (H2O2-forming)] inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; peripheral nervous system drug; plant metabolite
arecoline Arecoline: An alkaloid obtained from the betel nut (Areca catechu), fruit of a palm tree. It is an agonist at both muscarinic and nicotinic acetylcholine receptors. It is used in the form of various salts as a ganglionic stimulant, a parasympathomimetic, and a vermifuge, especially in veterinary practice. It has been used as a euphoriant in the Pacific Islands.. arecoline : A tetrahydropyridine that is 1,2,5,6-tetrahydropyridine with a methyl group at position 1, and a methoxycarbonyl group at position 3. An alkaloid found in the areca nut, it acts as an agonist of muscarinic acetylcholine.	2.13	1	0	enoate ester; methyl ester; pyridine alkaloid; tetrahydropyridine	metabolite; muscarinic agonist
aristolochic acid i aristolochic acid I: phospholipase A inhibitor. aristolochic acid A : An aristolochic acid that is phenanthrene-1-carboxylic acid that is substituted by a methylenedioxy group at the 3,4 positions, by a methoxy group at position 8, and by a nitro group at position 10. It is the most abundant of the aristolochic acids and is found in almost all Aristolochia (birthworts or pipevines) species. It has been tried in a number of treatments for inflammatory disorders, mainly in Chinese and folk medicine. However, there is concern over their use as aristolochic acid is both carcinogenic and nephrotoxic.	3.64	2	0	aristolochic acids; aromatic ether; C-nitro compound; cyclic acetal; monocarboxylic acid; organic heterotetracyclic compound	carcinogenic agent; metabolite; mutagen; nephrotoxin; toxin
aspirin Aspirin: The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5). acetylsalicylate : A benzoate that is the conjugate base of acetylsalicylic acid, arising from deprotonation of the carboxy group.. acetylsalicylic acid : A member of the class of benzoic acids that is salicylic acid in which the hydrogen that is attached to the phenolic hydroxy group has been replaced by an acetoxy group. A non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity.	8.28	6	0	benzoic acids; phenyl acetates; salicylates	anticoagulant; antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; EC 1.1.1.188 (prostaglandin-F synthase) inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; plant activator; platelet aggregation inhibitor; prostaglandin antagonist; teratogenic agent
astemizole Astemizole: Antihistamine drug now withdrawn from the market in many countries because of rare but potentially fatal side effects.. astemizole : A piperidine compound having a 2-(4-methoxyphenyl)ethyl group at the 1-position and an N-[(4-fluorobenzyl)benzimidazol-2-yl]amino group at the 4-position.	2.53	2	0	benzimidazoles; piperidines	anti-allergic agent; anticoronaviral agent; H1-receptor antagonist
atrazine [no description available]	4.94	11	0	chloro-1,3,5-triazine; diamino-1,3,5-triazine	environmental contaminant; herbicide; xenobiotic
azathioprine Azathioprine: An immunosuppressive agent used in combination with cyclophosphamide and hydroxychloroquine in the treatment of rheumatoid arthritis. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), this substance has been listed as a known carcinogen. (Merck Index, 11th ed). azathioprine : A thiopurine that is 6-mercaptopurine in which the mercapto hydrogen is replaced by a 1-methyl-4-nitroimidazol-5-yl group. It is a prodrug for mercaptopurine and is used as an immunosuppressant, prescribed for the treatment of inflammatory conditions and after organ transplantation and also for treatment of Crohn's didease and MS.	2.52	2	0	aryl sulfide; C-nitro compound; imidazoles; thiopurine	antimetabolite; antineoplastic agent; carcinogenic agent; DNA synthesis inhibitor; hepatotoxic agent; immunosuppressive agent; prodrug
benzyl isothiocyanate benzyl isothiocyanate: inhibits carcinogen-induced neoplasia; structure in Negwer, 5th ed, #715; also promotes urinary bladder carcinoma	5.04	13	0	benzenes; isothiocyanate	antibacterial drug
bepridil Bepridil: A long-acting calcium-blocking agent with significant anti-anginal activity. The drug produces significant coronary vasodilation and modest peripheral effects. It has antihypertensive and selective anti-arrhythmia activities and acts as a calmodulin antagonist.. bepridil : A tertiary amine in which the substituents on nitrogen are benzyl, phenyl and 3-(2-methylpropoxy)-2-(pyrrolidin-1-yl)propyl.	2	1	0	pyrrolidines; tertiary amine	anti-arrhythmia drug; antihypertensive agent; calcium channel blocker; vasodilator agent
berberine [no description available]	1.96	1	0	alkaloid antibiotic; berberine alkaloid; botanical anti-fungal agent; organic heteropentacyclic compound	antilipemic drug; antineoplastic agent; antioxidant; EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor; EC 1.21.3.3 (reticuline oxidase) inhibitor; EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor; EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor; EC 2.7.11.10 (IkappaB kinase) inhibitor; EC 3.1.1.4 (phospholipase A2) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; geroprotector; hypoglycemic agent; metabolite; potassium channel blocker
beta-naphthoflavone beta-Naphthoflavone: A polyaromatic hydrocarbon inducer of P4501A1 and P4501A2 cytochromes. (Proc Soc Exp Biol Med 1994 Dec:207(3):302-308). beta-naphthoflavone : An extended flavonoid resulting from the formal fusion of a benzene ring with the f side of flavone.	5.85	94	0	extended flavonoid; naphtho-gamma-pyrone; organic heterotricyclic compound	aryl hydrocarbon receptor agonist
propiolactone Propiolactone: Disinfectant used in vapor form to sterilize vaccines, grafts, etc. The vapor is very irritating and the liquid form is carcinogenic.	2.88	4	0	propan-3-olide
bicalutamide bicalutamide: approved for treatment of advanced prostate cancer. N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide : A member of the class of (trifluoromethyl)benzenes that is 4-amino-2-(trifluoromethyl)benzonitrile in which one of the amino hydrogens is substituted by a 3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanoyl group.. bicalutamide : A racemate comprising of equal amounts of (R)-bicalutamide and (S)-bicalutamide. It is an oral non-steroidal antiandrogen used in the treatment of prostate cancer and hirsutism.	2.6	1	0	(trifluoromethyl)benzenes; monocarboxylic acid amide; monofluorobenzenes; nitrile; sulfone; tertiary alcohol
busulfan [no description available]	2.11	1	0	methanesulfonate ester	alkylating agent; antineoplastic agent; carcinogenic agent; insect sterilant; teratogenic agent
caffeine [no description available]	10.15	15	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.	8.39	7	0	aromatic ether; nitrile; polyether; tertiary amino compound
carvedilol [no description available]	2.21	1	0	carbazoles; secondary alcohol; secondary amino compound	alpha-adrenergic antagonist; antihypertensive agent; beta-adrenergic antagonist; cardiovascular drug; vasodilator agent
celecoxib [no description available]	7.47	2	0	organofluorine compound; pyrazoles; sulfonamide; toluenes	cyclooxygenase 2 inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug
chloroquine Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.	2.11	1	0	aminoquinoline; organochlorine compound; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; antirheumatic drug; autophagy inhibitor; dermatologic drug
chlorpromazine Chlorpromazine: The prototypical phenothiazine antipsychotic drug. Like the other drugs in this class chlorpromazine's antipsychotic actions are thought to be due to long-term adaptation by the brain to blocking DOPAMINE RECEPTORS. Chlorpromazine has several other actions and therapeutic uses, including as an antiemetic and in the treatment of intractable hiccup.. chlorpromazine : A substituted phenothiazine in which the ring nitrogen at position 10 is attached to C-3 of an N,N-dimethylpropanamine moiety.	2.37	2	0	organochlorine compound; phenothiazines; tertiary amine	anticoronaviral agent; antiemetic; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; phenothiazine antipsychotic drug
chlorpyrifos Chlorpyrifos: An organothiophosphate cholinesterase inhibitor that is used as an insecticide and as an acaricide.. chlorpyrifos : An organic thiophosphate that is O,O-diethyl hydrogen phosphorothioate in which the hydrogen of the hydroxy group has been replaced by a 3,5,6-trichloropyridin-2-yl group.	8.77	10	0	chloropyridine; organic thiophosphate	acaricide; agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; environmental contaminant; insecticide; xenobiotic
cimetidine Cimetidine: A histamine congener, it competitively inhibits HISTAMINE binding to HISTAMINE H2 RECEPTORS. Cimetidine has a range of pharmacological actions. It inhibits GASTRIC ACID secretion, as well as PEPSIN and GASTRIN output.. cimetidine : A member of the class of guanidines that consists of guanidine carrying a methyl substituent at position 1, a cyano group at position 2 and a 2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl group at position 3. It is a H2-receptor antagonist that inhibits the production of acid in stomach.	2.37	2	0	aliphatic sulfide; guanidines; imidazoles; nitrile	adjuvant; analgesic; anti-ulcer drug; H2-receptor antagonist; P450 inhibitor
clofibrate angiokapsul: contains clofibrate & insoitolnicotinate	3.11	5	0	aromatic ether; ethyl ester; monochlorobenzenes	anticholesteremic drug; antilipemic drug; geroprotector; PPARalpha agonist
clotrimazole [no description available]	8.07	5	0	conazole antifungal drug; imidazole antifungal drug; imidazoles; monochlorobenzenes	antiinfective agent; environmental contaminant; xenobiotic
4-cresol 4-cresol: RN given refers to parent cpd. p-cresol : A cresol that consists of toluene substituted by a hydroxy group at position 4. It is a metabolite of aromatic amino acid metabolism produced by intestinal microflora in humans and animals.	1.97	1	0	cresol	Escherichia coli metabolite; human metabolite; uremic toxin
cypermethrin cypermethrin : A carboxylic ester resulting from the formal condensation between 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid and the alcoholic hydroxy group of hydroxy(3-phenoxyphenyl)acetonitrile.. zeta-cypermethrin : A diastereoisomeric mixture comprising the isomeric pair (1R)-cis-(alphaS)- and (1S)-trans-(alphaR)-cypermethrin together with the isomeric pair (1S)-cis-(alphaS)- and (1S)-trans-(alphaS)-cypermethrin where the ratio between the isomeric pairs lies in the range 45:55 to 55:45.	2.31	1	0	aromatic ether; cyclopropanecarboxylate ester; nitrile; organochlorine compound	agrochemical; molluscicide; pyrethroid ester acaricide; pyrethroid ester insecticide
damnacanthal damnacanthal: structure given in first source; isolated from the stem bark and roots of Morinda lucida; a selective inhibitor of p56(lck) tyrosine kinase activity	7.13	1	0	aldehyde; monohydroxyanthraquinone
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.	6.96	1	0	carboxamidine; isoquinolines	adrenergic agent; antihypertensive agent; human metabolite; sympatholytic agent
deferiprone Deferiprone: A pyridone derivative and iron chelator that is used in the treatment of IRON OVERLOAD in patients with THALASSEMIA.. deferiprone : A member of the class of 4-pyridones that is pyridin-4(1H)-one substituted at positions 1 and 2 by methyl groups and at position 3 by a hydroxy group. A lipid-soluble iron-chelator used for treatment of thalassaemia.	2.04	1	0	4-pyridones	iron chelator; protective agent
deferoxamine Deferoxamine: Natural product isolated from Streptomyces pilosus. It forms iron complexes and is used as a chelating agent, particularly in the mesylate form.. desferrioxamine B : An acyclic desferrioxamine that is butanedioic acid in which one of the carboxy groups undergoes formal condensation with the primary amino group of N-(5-aminopentyl)-N-hydroxyacetamide and the second carboxy group undergoes formal condensation with the hydroxyamino group of N(1)-(5-aminopentyl)-N(1)-hydroxy-N(4)-[5-(hydroxyamino)pentyl]butanediamide. It is a siderophore native to Streptomyces pilosus biosynthesised by the DesABCD enzyme cluster as a high affinity Fe(III) chelator.	2.04	1	0	acyclic desferrioxamine	bacterial metabolite; ferroptosis inhibitor; iron chelator; siderophore
amphetamine Amphetamine: A powerful central nervous system stimulant and sympathomimetic. Amphetamine has multiple mechanisms of action including blocking uptake of adrenergics and dopamine, stimulation of release of monamines, and inhibiting monoamine oxidase. Amphetamine is also a drug of abuse and a psychotomimetic. The l- and the d,l-forms are included here. The l-form has less central nervous system activity but stronger cardiovascular effects. The d-form is DEXTROAMPHETAMINE.. 1-phenylpropan-2-amine : A primary amine that is isopropylamine in which a hydrogen attached to one of the methyl groups has been replaced by a phenyl group.. amphetamine : A racemate comprising equimolar amounts of (R)-amphetamine (also known as levamphetamine or levoamphetamine) and (S)-amphetamine (also known as dexamfetamine or dextroamphetamine.	1.97	1	0	primary amine
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.	2.38	2	0	alpha-amino acid; fluoroamino acid	trypanocidal drug
diazepam Diazepam: A benzodiazepine with anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties and a long duration of action. Its actions are mediated by enhancement of GAMMA-AMINOBUTYRIC ACID activity.. diazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a methyl group at position 1 and a phenyl group at position 5.	2	1	0	1,4-benzodiazepinone; organochlorine compound	anticonvulsant; anxiolytic drug; environmental contaminant; sedative; xenobiotic
diazinon Diazinon: A cholinesterase inhibitor that is used as an organothiophosphorus insecticide.. diazinon : A member of the class of pyrimidines that is pyrimidine carrying an isopropyl group at position 2, a methyl group at position 6 and a (diethoxyphosphorothioyl)oxy group at position 4.	2.46	2	0	organic thiophosphate; pyrimidines	acaricide; agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; environmental contaminant; nematicide; xenobiotic
dibenzothiophene dibenzothiophene : A mancude organic heterotricyclic parent that consists of a thiophene ring flanked by two benzene rings ortho-fused across the 2,3- and 4,5-positions.	2.15	1	0	dibenzothiophenes; mancude organic heterotricyclic parent	keratolytic drug
dibutyl phthalate Dibutyl Phthalate: A plasticizer used in most plastics and found in water, air, soil, plants and animals. It may have some adverse effects with long-term exposure.. dibutyl phthalate : A phthalate ester that is the diester obtained by the formal condensation of the carboxy groups of phthalic acid with two molecules of butan-1-ol. Although used extensively as a plasticiser, it is a ubiquitous environmental contaminant that poses a risk to humans.	3.4	7	0	diester; phthalate ester	EC 3.2.1.20 (alpha-glucosidase) inhibitor; environmental contaminant; metabolite; plasticiser; teratogenic agent
diclofenac Diclofenac: A non-steroidal anti-inflammatory agent (NSAID) with antipyretic and analgesic actions. It is primarily available as the sodium salt.. diclofenac : A monocarboxylic acid consisting of phenylacetic acid having a (2,6-dichlorophenyl)amino group at the 2-position.	5.49	3	1	amino acid; aromatic amine; dichlorobenzene; monocarboxylic acid; secondary amino compound	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
dichlorodiphenyl dichloroethylene Dichlorodiphenyl Dichloroethylene: An organochlorine pesticide, it is the ethylene metabolite of DDT.	2.44	2	0	chlorophenylethylene; monochlorobenzenes	human xenobiotic metabolite; persistent organic pollutant
ddt 1,1-bis(p-chlorophenyl)-2,2,2-trichloroethane: structure in first source	6.39	22	0	benzenoid aromatic compound; chlorophenylethane; monochlorobenzenes; organochlorine insecticide	bridged diphenyl acaricide; carcinogenic agent; endocrine disruptor; persistent organic pollutant
pentetic acid Pentetic Acid: An iron chelating agent with properties like EDETIC ACID. DTPA has also been used as a chelator for other metals, such as plutonium.	2	1	0	pentacarboxylic acid	copper chelator
3,3'-diindolylmethane 3,3'-diindolylmethane: anti-inflammatory from edible cruciferous vegetables; a cytochrome P-450 antagonist	6.44	4	1	indoles	antineoplastic agent; P450 inhibitor
dimethoate Dimethoate: An organothiophosphorus cholinesterase inhibitor that is used as a systemic and contact insecticide.. dimethoate : A monocarboxylic acid amide that is N-methylacetamide in which one of the hydrogens of the methyl group attached to the carbonyl moiety is replaced by a (dimethoxyphosphorothioyl)sulfanediyl group.	2.31	1	0	monocarboxylic acid amide; organic thiophosphate	acaricide; agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; environmental contaminant; insecticide; xenobiotic
diphenyleneiodonium diphenyleneiodonium: structure in first source; NADPH oxidase inhibitor. dibenziodolium : An organic cation that is fluorene in which the methylene group is replaced by a positively charged iodine.	2.41	1	0	organic cation
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
disulfiram [no description available]	2.38	2	0	organic disulfide; organosulfur acaricide	angiogenesis inhibitor; antineoplastic agent; apoptosis inducer; EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor; EC 3.1.1.1 (carboxylesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 5.99.1.2 (DNA topoisomerase) inhibitor; ferroptosis inducer; fungicide; NF-kappaB inhibitor
dipropizine [no description available]	1.96	1	0	piperazines
ellipticine ellipticine : A organic heterotetracyclic compound that is pyrido[4,3-b]carbazole carrying two methyl substituents at positions 5 and 11.	8.51	8	0	indole alkaloid; organic heterotetracyclic compound; organonitrogen heterocyclic compound; polycyclic heteroarene	antineoplastic agent; plant metabolite
emodin Emodin: Purgative anthraquinone found in several plants, especially RHAMNUS PURSHIANA. It was formerly used as a laxative, but is now used mainly as a tool in toxicity studies.. emodin : A trihydroxyanthraquinone that is 9,10-anthraquinone which is substituted by hydroxy groups at positions 1, 3, and 8 and by a methyl group at position 6. It is present in the roots and barks of numerous plants (particularly rhubarb and buckthorn), moulds, and lichens. It is an active ingredient of various Chinese herbs.	4.92	2	1	trihydroxyanthraquinone	antineoplastic agent; laxative; plant metabolite; tyrosine kinase inhibitor
endosulfan Endosulfan: A polychlorinated compound used for controlling a variety of insects. It is practically water-insoluble, but readily adheres to clay particles and persists in soil and water for several years. Its mode of action involves repetitive nerve-discharges positively correlated to increase in temperature. This compound is extremely toxic to most fish. (From Comp Biochem Physiol (C) 1993 Jul;105(3):347-61). endosulfan : A cyclic sulfite ester that is 1,5,5a,6,9,9a-hexahydro-6,9-methano-2,4,3-benzodioxathiepine 3-oxide substituted by chloro groups at positions 6, 7, 8, 9, 10 and 10.	8.29	6	0	cyclic sulfite ester; cyclodiene organochlorine insecticide	acaricide; agrochemical; GABA-gated chloride channel antagonist; persistent organic pollutant
enflurane Enflurane: An extremely stable inhalation anesthetic that allows rapid adjustments of anesthesia depth with little change in pulse or respiratory rate.. enflurane : An ether in which the oxygen atom is connected to 2-chloro-1,1,2-trifluoroethyl and difluoromethyl groups.	2	1	0	ether; organochlorine compound; organofluorine compound	anaesthetic
erythrosine Fluoresceins: A family of spiro(isobenzofuran-1(3H),9'-(9H)xanthen)-3-one derivatives. These are used as dyes, as indicators for various metals, and as fluorescent labels in immunoassays.	3.08	5	0
ethacrynic acid Ethacrynic Acid: A compound that inhibits symport of sodium, potassium, and chloride primarily in the ascending limb of Henle, but also in the proximal and distal tubules. This pharmacological action results in excretion of these ions, increased urinary output, and reduction in extracellular fluid. This compound has been classified as a loop or high ceiling diuretic.. etacrynic acid : An aromatic ether that is phenoxyacetic acid in which the phenyl ring is substituted by chlorines at positions 2 and 3, and by a 2-methylidenebutanoyl group at position 4. It is a loop diuretic used to treat high blood pressure resulting from diseases such as congestive heart failure, liver failure, and kidney failure. It is also a glutathione S-transferase (EC 2.5.1.18) inhibitor.	2.92	4	0	aromatic ether; aromatic ketone; dichlorobenzene; monocarboxylic acid	EC 2.5.1.18 (glutathione transferase) inhibitor; ion transport inhibitor; loop diuretic
ethenzamide ethenzamide: structure	1.97	1	0	organic molecular entity
ether Ether: A mobile, very volatile, highly flammable liquid used as an inhalation anesthetic and as a solvent for waxes, fats, oils, perfumes, alkaloids, and gums. It is mildly irritating to skin and mucous membranes.. ether : An organooxygen compound with formula ROR, where R is not hydrogen.. diethyl ether : An ether in which the oxygen atom is linked to two ethyl groups.	2.08	1	0	ether; volatile organic compound	inhalation anaesthetic; non-polar solvent; refrigerant
ethoxyquin Ethoxyquin: Antioxidant; also a post-harvest dip to prevent scald on apples and pears.. ethoxyquin : A quinoline that is 1,2-dihydroquinoline bearing three methyl substituents at position 2, 2 and 4 as well as an ethoxy substituent at position 6.	1.96	1	0	aromatic ether; quinolines	antifungal agrochemical; food antioxidant; genotoxin; geroprotector; herbicide; Hsp90 inhibitor; neuroprotective agent; UDP-glucuronosyltransferase activator
ethoxyresorufin ethoxyresorufin: structure	9.7	29	0	phenoxazine
fipronil fipronil: has low mammalian toxicity; structure given in first source. fipronil : A racemate comprising equimolar amounts of (R)- and (S)-fipronil.. 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile : A member of the class of pyrazoles that is 1H-pyrazole that is substituted at positions 1, 3, 4, and 5 by 2,6-dichloro-4-(trifluoromethyl)phenyl, cyano, (trifluoromethyl)sulfinyl, and amino groups, respectively.	2.5	2	0	(trifluoromethyl)benzenes; dichlorobenzene; nitrile; primary amino compound; pyrazoles; sulfoxide
fluphenazine [no description available]	2	1	0	N-alkylpiperazine; organofluorine compound; phenothiazines	anticoronaviral agent; dopaminergic antagonist; phenothiazine antipsychotic drug
fluorouracil Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.	3.27	6	0	nucleobase analogue; organofluorine compound	antimetabolite; antineoplastic agent; environmental contaminant; immunosuppressive agent; radiosensitizing agent; xenobiotic
fluoxetine Fluoxetine: The first highly specific serotonin uptake inhibitor. It is used as an antidepressant and often has a more acceptable side-effects profile than traditional antidepressants.. fluoxetine : A racemate comprising equimolar amounts of (R)- and (S)-fluoxetine. A selective serotonin reuptake inhibitor (SSRI), it is used (generally as the hydrochloride salt) for the treatment of depression (and the depressive phase of bipolar disorder), bullimia nervosa, and obsessive-compulsive disorder.. N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine : An aromatic ether consisting of 4-trifluoromethylphenol in which the hydrogen of the phenolic hydroxy group is replaced by a 3-(methylamino)-1-phenylpropyl group.	7.07	1	0	(trifluoromethyl)benzenes; aromatic ether; secondary amino compound
flurbiprofen Flurbiprofen: An anti-inflammatory analgesic and antipyretic of the phenylalkynoic acid series. It has been shown to reduce bone resorption in periodontal disease by inhibiting CARBONIC ANHYDRASE.. flurbiprofen : A monocarboxylic acid that is a 2-fluoro-[1,1'-biphenyl-4-yl] moiety linked to C-2 of propionic acid. A non-steroidal anti-inflammatory, analgesic and antipyretic, it is used as a pre-operative anti-miotic as well as orally for arthritis or dental pain.	2.07	1	0	fluorobiphenyl; monocarboxylic acid	antipyretic; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
fomepizole Fomepizole: A pyrazole and competitive inhibitor of ALCOHOL DEHYDROGENASE that is used for the treatment of poisoning by ETHYLENE GLYCOL or METHANOL.. fomepizole : A member of the class of pyrazoles that is 1H-pyrazole substituted by a methyl group at position 4.	1.97	1	0	pyrazoles	antidote; EC 1.1.1.1 (alcohol dehydrogenase) inhibitor; protective agent
furosemide Furosemide: A benzoic-sulfonamide-furan. It is a diuretic with fast onset and short duration that is used for EDEMA and chronic RENAL INSUFFICIENCY.. furosemide : A chlorobenzoic acid that is 4-chlorobenzoic acid substituted by a (furan-2-ylmethyl)amino and a sulfamoyl group at position 2 and 5 respectively. It is a diuretic used in the treatment of congestive heart failure.	2.74	3	0	chlorobenzoic acid; furans; sulfonamide	environmental contaminant; loop diuretic; xenobiotic
gentamicin Gentamicins: A complex of closely related aminoglycosides obtained from MICROMONOSPORA purpurea and related species. They are broad-spectrum antibiotics, but may cause ear and kidney damage. They act to inhibit PROTEIN BIOSYNTHESIS.	2.25	1	0
glutaral Glutaral: One of the protein CROSS-LINKING REAGENTS that is used as a disinfectant for sterilization of heat-sensitive equipment and as a laboratory reagent, especially as a fixative.. glutaraldehyde : A dialdehyde comprised of pentane with aldehyde functions at C-1 and C-5.	2	1	0	dialdehyde	cross-linking reagent; disinfectant; fixative
glutethimide Glutethimide: A hypnotic and sedative. Its use has been largely superseded by other drugs.	1.98	1	0	piperidines
glyburide Glyburide: An antidiabetic sulfonylurea derivative with actions like those of chlorpropamide. glyburide : An N-sulfonylurea that is acetohexamide in which the acetyl group is replaced by a 2-(5-chloro-2-methoxybenzamido)ethyl group.	2.31	1	0	monochlorobenzenes; N-sulfonylurea	anti-arrhythmia drug; EC 2.7.1.33 (pantothenate kinase) inhibitor; EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor; hypoglycemic agent
glyphosate glyphosate: active cpd in herbicidal formulation Roundup; inhibits EC 2.5.1.19, 5-enolpyruvylshikimate-3-phosphate synthase; structure. glyphosate : A phosphonic acid resulting from the formal oxidative coupling of the methyl group of methylphosphonic acid with the amino group of glycine. It is one of the most commonly used herbicides worldwide, and the only one to target the enzyme 5-enolpyruvyl-3-shikimate phosphate synthase (EPSPS).	2.42	2	0	glycine derivative; phosphonic acid	agrochemical; EC 2.5.1.19 (3-phosphoshikimate 1-carboxyvinyltransferase) inhibitor; herbicide
guaifenesin Guaifenesin: An expectorant that also has some muscle relaxing action. It is used in many cough preparations.	2.78	3	0	methoxybenzenes
guanethidine Guanethidine: An antihypertensive agent that acts by inhibiting selectively transmission in post-ganglionic adrenergic nerves. It is believed to act mainly by preventing the release of norepinephrine at nerve endings and causes depletion of norepinephrine in peripheral sympathetic nerve terminals as well as in tissues.. guanethidine : A member of the class of guanidines in which one of the hydrogens of the amino group has been replaced by a 2-azocan-1-ylethyl group.. guanethidine sulfate : A organic sulfate salt composed of two molecules of guanethidine and one of sulfuric acid.	2.44	2	0	azocanes; guanidines	adrenergic antagonist; antihypertensive agent; sympatholytic agent
halothane [no description available]	1.96	1	0	haloalkane; organobromine compound; organochlorine compound; organofluorine compound	inhalation anaesthetic
heptachlor Heptachlor: A man-made compound previously used to control termites and other insects. Even though production of heptachlor was phased out of use in the United States during the late 1980's it remains in soil and hazardous waste sites. It is clearly toxic to animals and humans but, the International Agency for Research on Cancer (IARC) has determined that heptachlor is not classifiable as to its carcinogenicity to humans. (From ATSDR Public Heath Statement, April 1989). heptachlor : A cyclodiene organochlorine insecticide that is 3a,4,7,7a-tetrahydro-1H-4,7-methanoindene substituted by chlorine atoms at positions 1, 4, 5, 6, 7, 8 and 8. Formerly used to kill termites, ants and other insects in agricultural and domestic situations.	1.96	1	0	cyclodiene organochlorine insecticide	agrochemical; antibacterial agent; antifungal agent; GABA-gated chloride channel antagonist; persistent organic pollutant
miltefosine miltefosine: hexadecyl phosphocholine derivative of cisplatin; did not substantially activate HIV long terminal repeat; less toxic than cisplatin. miltefosine : A phospholipid that is the hexadecyl monoester of phosphocholine.	1.98	1	0	phosphocholines; phospholipid	anti-inflammatory agent; anticoronaviral agent; antifungal agent; antineoplastic agent; antiprotozoal drug; apoptosis inducer; immunomodulator; protein kinase inhibitor
hexobarbital Hexobarbital: A barbiturate that is effective as a hypnotic and sedative.. hexobarbital : A member of the class of barbiturates taht is barbituric acid substituted at N-1 by methyl and at C-5 by methyl and cyclohex-1-enyl groups.	3.98	4	0	barbiturates
ethidium Ethidium: A trypanocidal agent and possible antiviral agent that is widely used in experimental cell biology and biochemistry. Ethidium has several experimentally useful properties including binding to nucleic acids, noncompetitive inhibition of nicotinic acetylcholine receptors, and fluorescence among others. It is most commonly used as the bromide.. ethidium : The fluorescent compound widely used in experimental cell biology and biochemistry to reveal double-stranded DNA and RNA.	2.89	4	0	phenanthridines	fluorochrome; intercalator
hydralazine Hydralazine: A direct-acting vasodilator that is used as an antihypertensive agent.. hydralazine : The 1-hydrazino derivative of phthalazine; a direct-acting vasodilator that is used as an antihypertensive agent.	1.98	1	0	azaarene; hydrazines; ortho-fused heteroarene; phthalazines	antihypertensive agent; vasodilator agent
hydroxyurea [no description available]	9.05	15	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
ibuprofen Midol: combination of cinnamedrine, phenacetin, aspirin & caffeine	2.54	2	0	monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; radical scavenger; xenobiotic
imipramine Imipramine: The prototypical tricyclic antidepressant. It has been used in major depression, dysthymia, bipolar depression, attention-deficit disorders, agoraphobia, and panic disorders. It has less sedative effect than some other members of this therapeutic group.. imipramine : A dibenzoazepine that is 5H-dibenzo[b,f]azepine substituted by a 3-(dimethylamino)propyl group at the nitrogen atom.	1.96	1	0	dibenzoazepine	adrenergic uptake inhibitor; antidepressant; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
indirubin-3'-monoxime indirubin-3'-monoxime: has antiangiogenic activity. indirubin-3'-monoxime : A member of the class of biindoles that is indirubin in which the keto group at position 3' has undergone condensation with hydroxylamine to form the corresponding oxime.	2.05	1	0
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.	11.54	14	0	indolyl alcohol	antineoplastic agent; plant metabolite
indomethacin Indomethacin: A non-steroidal anti-inflammatory agent (NSAID) that inhibits CYCLOOXYGENASE, which is necessary for the formation of PROSTAGLANDINS and other AUTACOIDS. It also inhibits the motility of POLYMORPHONUCLEAR LEUKOCYTES.. indometacin : A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by p-chlorobenzoyl, methyl, and methoxy groups, respectively. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis.	3.57	9	0	aromatic ether; indole-3-acetic acids; monochlorobenzenes; N-acylindole	analgesic; drug metabolite; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; gout suppressant; non-steroidal anti-inflammatory drug; xenobiotic metabolite; xenobiotic
isoniazid Hydra: A genus of freshwater polyps in the family Hydridae, order Hydroida, class HYDROZOA. They are of special interest because of their complex organization and because their adult organization corresponds roughly to the gastrula of higher animals.. hydrazide : Compounds derived from oxoacids RkE(=O)l(OH)m (l =/= 0) by replacing -OH by -NRNR2 (R groups are commonly H). (IUPAC).	2	1	0	carbohydrazide	antitubercular agent; drug allergen
ketoconazole 1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine : A dioxolane that is 1,3-dioxolane which is substituted at positions 2, 2, and 4 by imidazol-1-ylmethyl, 2,4-dichlorophenyl, and [para-(4-acetylpiperazin-1-yl)phenoxy]methyl groups, respectively.	3.13	5	0	dichlorobenzene; dioxolane; ether; imidazoles; N-acylpiperazine; N-arylpiperazine
ketoprofen Ketoprofen: An IBUPROFEN-type anti-inflammatory analgesic and antipyretic. It is used in the treatment of rheumatoid arthritis and osteoarthritis.. ketoprofen : An oxo monocarboxylic acid that consists of propionic acid substituted by a 3-benzoylphenyl group at position 2.	4.9	1	1	benzophenones; oxo monocarboxylic acid	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-steroidal anti-inflammatory drug; xenobiotic
khellin Khellin: A vasodilator that also has bronchodilatory action. It has been employed in the treatment of angina pectoris, in the treatment of asthma, and in conjunction with ultraviolet light A, has been tried in the treatment of vitiligo. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1024). khellin : A furanochrome in which the basic tricyclic skeleton is substituted at positions 4 and 9 with methoxy groups and at position 7 with a methyl group. A major constituent of the plant Ammi visnaga it is a herbal folk medicine used for various illnesses, its main effect being as a vasodilator.	1.99	1	0	furanochromone; organic heterotricyclic compound; oxacycle	anti-asthmatic agent; bronchodilator agent; cardiovascular drug; vasodilator agent
lauric acid dodecanoic acid : A straight-chain, twelve-carbon medium-chain saturated fatty acid with strong bactericidal properties; the main fatty acid in coconut oil and palm kernel oil.	1.98	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; antibacterial agent; plant metabolite
lomustine [no description available]	1.97	1	0	N-nitrosoureas; organochlorine compound	alkylating agent; antineoplastic agent
losartan Losartan: An antagonist of ANGIOTENSIN TYPE 1 RECEPTOR with antihypertensive activity due to the reduced pressor effect of ANGIOTENSIN II.. losartan : A biphenylyltetrazole where a 1,1'-biphenyl group is attached at the 5-position and has an additional trisubstituted imidazol-1-ylmethyl group at the 4'-position	4.9	1	1	biphenylyltetrazole; imidazoles	angiotensin receptor antagonist; anti-arrhythmia drug; antihypertensive agent; endothelin receptor antagonist
malathion Malathion: A wide spectrum aliphatic organophosphate insecticide widely used for both domestic and commercial agricultural purposes.. malathion : A racemate comprising equimolar amounts of (R) and (S)-malathion. It is a broad spectrum organophosphate proinsecticide used to control a wide range of pests including Coleoptera, Diptera, fruit flies, mosquitos and spider mites.. diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate : A diester that is diethyl succinate in which position 2 is substituted by a (dimethoxyphosphorothioyl)thio group.	2.04	1	0	diester; ethyl ester; organic thiophosphate
diisopropyl 1,3-dithiol-2-ylidenemalonate diisopropyl 1,3-dithiol-2-ylidenemalonate: structure in first source	1.97	1	0	isopropyl ester
mazindol Mazindol: Tricyclic anorexigenic agent unrelated to and less toxic than AMPHETAMINE, but with some similar side effects. It inhibits uptake of catecholamines and blocks the binding of cocaine to the dopamine uptake transporter.	1.96	1	0	organic molecular entity
edaravone [no description available]	4.9	1	1	pyrazolone	antioxidant; radical scavenger
vitamin k 3 Vitamin K 3: A synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo.	3.31	6	0	1,4-naphthoquinones; vitamin K	angiogenesis inhibitor; antineoplastic agent; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; human urinary metabolite; nutraceutical
mephenytoin Mephenytoin: An anticonvulsant effective in tonic-clonic epilepsy (EPILEPSY, TONIC-CLONIC). It may cause blood dyscrasias.. mephenytoin : An imidazolidine-2,4-dione (hydantoin) in which the imidazolidine nucleus carries a methyl group at N-3 and has ethyl and phenyl substituents at C-5. An anticonvulsant, it is no longer available in the USA or the UK but is still studied largely because of its interesting hydroxylation polymorphism.	4.9	1	1	imidazolidine-2,4-dione	anticonvulsant
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.	2.55	2	0	guanidines	environmental contaminant; geroprotector; hypoglycemic agent; xenobiotic
methacrylic acid methacrylic acid: RN given refers to parent cpd. methacrylic acid : An alpha,beta-unsaturated monocarboxylic acid that is acrylic acid in which the hydrogen at position 2 is substituted by a methyl group.	2.49	2	0	alpha,beta-unsaturated monocarboxylic acid
methadone Methadone: A synthetic opioid that is used as the hydrochloride. It is an opioid analgesic that is primarily a mu-opioid agonist. It has actions and uses similar to those of MORPHINE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1082-3). methadone : A racemate comprising equimolar amounts of dextromethadone and levomethadone. It is a opioid analgesic which is used as a painkiller and as a substitute for heroin in the treatment of heroin addiction.. 6-(dimethylamino)-4,4-diphenylheptan-3-one : A ketone that is heptan-3-one substituted by a dimethylamino group at position 6 and two phenyl groups at position 4.	1.96	1	0	benzenes; diarylmethane; ketone; tertiary amino compound
methapyrilene Methapyrilene: Histamine H1 antagonist with sedative action used as a hypnotic and in allergies.. methapyrilene : A member of the class of ethylenediamine derivatives that is ethylenediamine in which one of the nitrogens is substituted by two methyl groups, and the other nitrogen is substituted by a 2-pyridyl group and a (2-thienyl)methyl group.	2.17	1	0	ethylenediamine derivative	anti-allergic agent; carcinogenic agent; H1-receptor antagonist; sedative
methoxsalen Methoxsalen: A naturally occurring furocoumarin compound found in several species of plants, including Psoralea corylifolia. It is a photoactive substance that forms DNA ADDUCTS in the presence of ultraviolet A irradiation.. methoxsalen : A member of the class of psoralens that is 7H-furo[3,2-g]chromen-7-one in which the 9 position is substituted by a methoxy group. It is a constituent of the fruits of Ammi majus. Like other psoralens, trioxsalen causes photosensitization of the skin. It is administered topically or orally in conjunction with UV-A for phototherapy treatment of vitiligo and severe psoriasis.	3.24	6	0	aromatic ether; psoralens	antineoplastic agent; cross-linking reagent; dermatologic drug; photosensitizing agent; plant metabolite
methoxychlor Methoxychlor: An insecticide. Methoxychlor has estrogenic effects in mammals, among other effects.	7.51	2	0	organochlorine insecticide
nocodazole [no description available]	1.99	1	0	aromatic ketone; benzimidazoles; carbamate ester; thiophenes	antimitotic; antineoplastic agent; microtubule-destabilising agent; tubulin modulator
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.	2.44	2	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
methyl methanesulfonate [no description available]	9.97	38	0	methanesulfonate ester	alkylating agent; apoptosis inducer; carcinogenic agent; genotoxin; mutagen
metronidazole Metronidazole: A nitroimidazole used to treat AMEBIASIS; VAGINITIS; TRICHOMONAS INFECTIONS; GIARDIASIS; ANAEROBIC BACTERIA; and TREPONEMAL INFECTIONS.. metronidazole : A member of the class of imidazoles substituted at C-1, -2 and -5 with 2-hydroxyethyl, nitro and methyl groups respectively. It has activity against anaerobic bacteria and protozoa, and has a radiosensitising effect on hypoxic tumour cells. It may be given by mouth in tablets, or as the benzoate in an oral suspension. The hydrochloride salt can be used in intravenous infusions. Metronidazole is a prodrug and is selective for anaerobic bacteria due to their ability to intracellularly reduce the nitro group of metronidazole to give nitroso-containing intermediates. These can covalently bind to DNA, disrupting its helical structure, inducing DNA strand breaks and inhibiting bacterial nucleic acid synthesis, ultimately resulting in bacterial cell death.	2.01	1	0	C-nitro compound; imidazoles; primary alcohol	antiamoebic agent; antibacterial drug; antimicrobial agent; antiparasitic agent; antitrichomonal drug; environmental contaminant; prodrug; radiosensitizing agent; xenobiotic
metyrapone Metyrapone: An inhibitor of the enzyme STEROID 11-BETA-MONOOXYGENASE. It is used as a test of the feedback hypothalamic-pituitary mechanism in the diagnosis of CUSHING SYNDROME.. metyrapone : An aromatic ketone that is 3,3-dimethylbutan-2-one in which the methyl groups at positions 1 and 4 are replaced by pyridin-3-yl groups. A steroid 11beta-monooxygenase (EC 1.14.15.4) inhibitor, it is used in the diagnosis of adrenal insufficiency.	3.22	6	0	aromatic ketone	antimetabolite; diagnostic agent; EC 1.14.15.4 (steroid 11beta-monooxygenase) inhibitor
miconazole Miconazole: An imidazole antifungal agent that is used topically and by intravenous infusion.. 1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole : A member of the class of imidazoles that is 1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanol in which the hydroxyl hydrogen is replaced by a 2,4-dichlorobenzyl group.. miconazole : A racemate composed of equimolar amounts of (R)- and (S)-miconazole. Used (as its nitrate salt) to treat skin infections such as athlete's foot, jock itch, ringworm and other fungal skin infections. It inhibits the synthesis of ergosterol, a critical component of fungal cell membranes.	2.37	2	0	dichlorobenzene; ether; imidazoles
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.	1.97	1	0	dihydroxyanthraquinone	analgesic; antineoplastic agent
molsidomine Molsidomine: A morpholinyl sydnone imine ethyl ester, having a nitrogen in place of the keto oxygen. It acts as NITRIC OXIDE DONORS and is a vasodilator that has been used in ANGINA PECTORIS.. molsidomine : A member of the class of oxadiazoles that is 1,2,3-oxadiazole substituted by morpholin-4-yl and (ethoxycarbonyl)azanidyl groups at positions 3 and 5, respectively. It is used as a vasodilator drug for the treatment of myocardial ischemic syndrome and congestive heart failure.	2	1	0	ethyl ester; morpholines; oxadiazole; zwitterion	antioxidant; apoptosis inhibitor; cardioprotective agent; nitric oxide donor; vasodilator agent
myristicin myristicin: asaricin is an isomer; structure; a methylene dioxy version of elemicin;	1.98	1	0	organic molecular entity	metabolite
ethylmaleimide Ethylmaleimide: A sulfhydryl reagent that is widely used in experimental biochemical studies.	1.98	1	0	maleimides	anticoronaviral agent; EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor; EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor; EC 2.7.1.1 (hexokinase) inhibitor
nalidixic acid [no description available]	2.37	2	0	1,8-naphthyridine derivative; monocarboxylic acid; quinolone antibiotic	antibacterial drug; antimicrobial agent; DNA synthesis inhibitor
nitrendipine Nitrendipine: A calcium channel blocker with marked vasodilator action. It is an effective antihypertensive agent and differs from other calcium channel blockers in that it does not reduce glomerular filtration rate and is mildly natriuretic, rather than sodium retentive.. nitrendipine : A dihydropyridine that is 1,4-dihydropyridine substituted by methyl groups at positions 2 and 6, a 3-nitrophenyl group at position 4, a ethoxycarbonyl group at position 3 and a methoxycarbonyl group at position 5. It is a calcium-channel blocker used in the treatment of hypertension.	7.06	1	0	C-nitro compound; dicarboxylic acids and O-substituted derivatives; diester; dihydropyridine; ethyl ester; methyl ester	antihypertensive agent; calcium channel blocker; geroprotector; vasodilator agent
omeprazole Omeprazole: A 4-methoxy-3,5-dimethylpyridyl, 5-methoxybenzimidazole derivative of timoprazole that is used in the therapy of STOMACH ULCERS and ZOLLINGER-ELLISON SYNDROME. The drug inhibits an H(+)-K(+)-EXCHANGING ATPASE which is found in GASTRIC PARIETAL CELLS.. omeprazole : A racemate comprising equimolar amounts of (R)- and (S)-omeprazole.. 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole : A member of the class of benzimidazoles that is 1H-benzimidazole which is substituted by a [4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl group at position 2 and a methoxy group at position 5.	5.95	4	1	aromatic ether; benzimidazoles; pyridines; sulfoxide
oxazepam Oxazepam: A benzodiazepine used in the treatment of anxiety, alcohol withdrawal, and insomnia.. oxazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a hydroxy group at position 3 and phenyl group at position 5.	3.1	1	0	1,4-benzodiazepinone; organochlorine compound	anxiolytic drug; environmental contaminant; xenobiotic
oxyphenbutazone Oxyphenbutazone: A non-steroidal anti-inflammatory drug. Oxyphenbutazone eyedrops have been used abroad in the management of postoperative ocular inflammation, superficial eye injuries, and episcleritis. (From AMA, Drug Evaluations Annual, 1994, p2000) It had been used by mouth in rheumatic disorders such as ankylosing spondylitis, osteoarthritis, and rheumatoid arthritis but such use is no longer considered justified owing to the risk of severe hematological adverse effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p27). oxyphenbutazone : A metabolite of phenylbutazone obtained by hydroxylation at position 4 of one of the phenyl rings. Commonly used (as its hydrate) to treat pain, swelling and stiffness associated with arthritis and gout, it was withdrawn from the market 1984 following association with blood dyscrasis and Stevens-Johnson syndrome.	3.05	1	0	phenols; pyrazolidines	antimicrobial agent; antineoplastic agent; antipyretic; drug metabolite; gout suppressant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic metabolite
quinone benzoquinone : The simplest members of the class of benzoquinones, consisting of cyclohexadiene which is substituted by two oxo groups.. 1,4-benzoquinone : The simplest member of the class of 1,4-benzoquinones, obtained by the formal oxidation of hydroquinone to the corresponding diketone. It is a metabolite of benzene.. quinone : Compounds having a fully conjugated cyclic dione structure, such as that of benzoquinones, derived from aromatic compounds by conversion of an even number of -CH= groups into -C(=O)- groups with any necessary rearrangement of double bonds (polycyclic and heterocyclic analogues are included).	2.69	3	0	1,4-benzoquinones	cofactor; human xenobiotic metabolite; mouse metabolite
4-dichlorobenzene dichlorobenzene : Any member of the class of chlorobenzenes carrying two chloro groups at unspecified positions.. 1,4-dichlorobenzene : A dichlorobenzene carrying chloro groups at positions 1 and 4.	2.04	1	0	dichlorobenzene	insecticide
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'.	3.54	8	0	aromatic amine; monomethoxyflavone	EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector
pentobarbital Pentobarbital: A short-acting barbiturate that is effective as a sedative and hypnotic (but not as an anti-anxiety) agent and is usually given orally. It is prescribed more frequently for sleep induction than for sedation but, like similar agents, may lose its effectiveness by the second week of continued administration. (From AMA Drug Evaluations Annual, 1994, p236). pentobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and sec-pentyl groups.	1.96	1	0	barbiturates	GABAA receptor agonist
phenacetin Saridon: contains phenacetin, caffeine, propyphenazone & pyrithyldione	2.66	3	0	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.	9.36	89	1	barbiturates	anticonvulsant; drug allergen; excitatory amino acid antagonist; sedative
phenolphthalein Phenolphthalein: An acid-base indicator which is colorless in acid solution, but turns pink to red as the solution becomes alkaline. It is used medicinally as a cathartic.	3.1	1	0	phenols
phenolsulfonphthalein Phenolsulfonphthalein: Red dye, pH indicator, and diagnostic aid for determination of renal function. It is used also for studies of the gastrointestinal and other systems.. phenol red : 3H-2,1-Benzoxathiole 1,1-dioxide in which both of the hydrogens at position 3 have been substituted by 4-hydroxyphenyl groups. A pH indicator changing colour from yellow below pH 6.8 to bright pink above pH 8.2, it is commonly used as an indicator in cell cultures and in home swimming pool test kits. It is also used in the (now infrequently performed) phenolsulfonphthalein (PSP) test for estimation of overall blood flow through the kidney.	2.31	1	0	2,1-benzoxathiole; arenesulfonate ester; phenols; sultone	acid-base indicator; diagnostic agent; two-colour indicator
4-phenylbutyric acid 4-phenylbutyric acid: RN refers to the parent cpd. 4-phenylbutyric acid : A monocarboxylic acid the structure of which is that of butyric acid substituted with a phenyl group at C-4. It is a histone deacetylase inhibitor that displays anticancer activity. It inhibits cell proliferation, invasion and migration and induces apoptosis in glioma cells. It also inhibits protein isoprenylation, depletes plasma glutamine, increases production of foetal haemoglobin through transcriptional activation of the gamma-globin gene and affects hPPARgamma activation.	2.6	1	0	monocarboxylic acid	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor; prodrug
phenylbutazone Phenylbutazone: A butyl-diphenyl-pyrazolidinedione that has anti-inflammatory, antipyretic, and analgesic activities. It has been used in ANKYLOSING SPONDYLITIS; RHEUMATOID ARTHRITIS; and REACTIVE ARTHRITIS.. phenylbutazone : A member of the class of pyrazolidines that is 1,2-diphenylpyrazolidine-3,5-dione carrying a butyl group at the 4-position.	3.05	1	0	pyrazolidines	antirheumatic drug; EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor; metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; peripheral nervous system drug
phenylmethylsulfonyl fluoride Phenylmethylsulfonyl Fluoride: An enzyme inhibitor that inactivates IRC-50 arvin, subtilisin, and the fatty acid synthetase complex.. phenylmethanesulfonyl fluoride : An acyl fluoride with phenylmethanesulfonyl as the acyl group.	1.98	1	0	acyl fluoride	serine proteinase inhibitor
pifithrin pifithrin: a tetrahydrobenzothiazol; inhibitor of P53 that protects mice from the side effects of cancer therapy; structure in first source	2.95	4	0	aromatic ketone
pioglitazone Pioglitazone: A thiazolidinedione and PPAR GAMMA agonist that is used in the treatment of TYPE 2 DIABETES MELLITUS.. pioglitazone : A member of the class of thiazolidenediones that is 1,3-thiazolidine-2,4-dione substituted by a benzyl group at position 5 which in turn is substituted by a 2-(5-ethylpyridin-2-yl)ethoxy group at position 4 of the phenyl ring. It exhibits hypoglycemic activity.	2.06	1	0	aromatic ether; pyridines; thiazolidinediones	antidepressant; cardioprotective agent; EC 2.7.1.33 (pantothenate kinase) inhibitor; EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor; ferroptosis inhibitor; geroprotector; hypoglycemic agent; insulin-sensitizing drug; PPARgamma agonist; xenobiotic
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.	2.43	2	0	aromatic ether; furans; monocarboxylic acid amide; piperazines; quinazolines	alpha-adrenergic antagonist; antihypertensive agent; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
primaquine Primaquine: An aminoquinoline that is given by mouth to produce a radical cure and prevent relapse of vivax and ovale malarias following treatment with a blood schizontocide. It has also been used to prevent transmission of falciparum malaria by those returning to areas where there is a potential for re-introduction of malaria. Adverse effects include anemias and GI disturbances. (From Martindale, The Extra Pharmacopeia, 30th ed, p404). primaquine : An N-substituted diamine that is pentane-1,4-diamine substituted by a 6-methoxyquinolin-8-yl group at the N(4) position. It is a drug used in the treatment of malaria and Pneumocystis pneumonia.	2.11	1	0	aminoquinoline; aromatic ether; N-substituted diamine	antimalarial
proadifen Proadifen: An inhibitor of drug metabolism and CYTOCHROME P-450 ENZYME SYSTEM activity.	2.89	4	0	diarylmethane
probenecid Probenecid: The prototypical uricosuric agent. It inhibits the renal excretion of organic anions and reduces tubular reabsorption of urate. Probenecid has also been used to treat patients with renal impairment, and, because it reduces the renal tubular excretion of other drugs, has been used as an adjunct to antibacterial therapy.. probenecid : A sulfonamide in which the nitrogen of 4-sulfamoylbenzoic acid is substituted with two propyl groups.	7.93	4	0	benzoic acids; sulfonamide	uricosuric drug
probucol Probucol: A drug used to lower LDL and HDL cholesterol yet has little effect on serum-triglyceride or VLDL cholesterol. (From Martindale, The Extra Pharmacopoeia, 30th ed, p993).. probucol : A dithioketal that is propane-2,2-dithiol in which the hydrogens attached to both sulfur atoms are replaced by 3,5-di-tert-butyl-4-hydroxyphenyl groups. An anticholesteremic drug with antioxidant and anti-inflammatory properties, it is used to treat high levels of cholesterol in blood.	1.98	1	0	dithioketal; polyphenol	anti-inflammatory drug; anticholesteremic drug; antilipemic drug; antioxidant; cardiovascular drug
procaine Procaine: A local anesthetic of the ester type that has a slow onset and a short duration of action. It is mainly used for infiltration anesthesia, peripheral nerve block, and spinal block. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1016).. procaine : A benzoate ester, formally the result of esterification of 4-aminobenzoic acid with 2-diethylaminoethanol but formed experimentally by reaction of ethyl 4-aminobenzoate with 2-diethylaminoethanol.	2.7	3	0	benzoate ester; substituted aniline; tertiary amino compound	central nervous system depressant; drug allergen; local anaesthetic; peripheral nervous system drug
procarbazine Procarbazine: An antineoplastic agent used primarily in combination with mechlorethamine, vincristine, and prednisone (the MOPP protocol) in the treatment of Hodgkin's disease.. procarbazine : A benzamide obtained by formal condensation of the carboxy group of 4-[(2-methylhydrazino)methyl]benzoic acid with the amino group of isopropylamine. An antineoplastic chemotherapy drug used for treatment of Hodgkin's lymphoma. Metabolism yields azo-procarbazine and hydrogen peroxide, which results in the breaking of DNA strands.	2.36	2	0	benzamides; hydrazines	antineoplastic agent
propofol Propofol: An intravenous anesthetic agent which has the advantage of a very rapid onset after infusion or bolus injection plus a very short recovery period of a couple of minutes. (From Smith and Reynard, Textbook of Pharmacology, 1992, 1st ed, p206). Propofol has been used as ANTICONVULSANTS and ANTIEMETICS.. propofol : A phenol resulting from the formal substitution of the hydrogen at the 2 position of 1,3-diisopropylbenzene by a hydroxy group.	2.4	2	0	phenols	anticonvulsant; antiemetic; intravenous anaesthetic; radical scavenger; sedative
propoxur Propoxur: A carbamate insecticide.. propoxur : A carbamate ester that is phenyl methylcarbamate substituted at position 2 by a propan-2-yloxy group.	2.05	1	0	aromatic ether; carbamate ester	acaricide; agrochemical; carbamate insecticide; EC 3.1.1.7 (acetylcholinesterase) inhibitor
propranolol Propranolol: A widely used non-cardioselective beta-adrenergic antagonist. Propranolol has been used for MYOCARDIAL INFARCTION; ARRHYTHMIA; ANGINA PECTORIS; HYPERTENSION; HYPERTHYROIDISM; MIGRAINE; PHEOCHROMOCYTOMA; and ANXIETY but adverse effects instigate replacement by newer drugs.. propranolol : A propanolamine that is propan-2-ol substituted by a propan-2-ylamino group at position 1 and a naphthalen-1-yloxy group at position 3.	2.89	4	0	naphthalenes; propanolamine; secondary amine	anti-arrhythmia drug; antihypertensive agent; anxiolytic drug; beta-adrenergic antagonist; environmental contaminant; human blood serum metabolite; vasodilator agent; xenobiotic
propyl gallate Propyl Gallate: Antioxidant for foods, fats, oils, ethers, emulsions, waxes, and transformer oils.	3.99	4	0	trihydroxybenzoic acid
pyrimethamine Maloprim: contains above 2 cpds	2.11	1	0	aminopyrimidine; monochlorobenzenes	antimalarial; antiprotozoal drug; EC 1.5.1.3 (dihydrofolate reductase) inhibitor
resorcinol resorcinol: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7951. resorcinol : A benzenediol that is benzene dihydroxylated at positions 1 and 3.	1.96	1	0	benzenediol; phenolic donor; resorcinols	erythropoietin inhibitor; sensitiser
rolipram [no description available]	2.1	1	0	pyrrolidin-2-ones	antidepressant; EC 3.1.4.* (phosphoric diester hydrolase) 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.	10.66	15	0	benzodioxoles	flavouring agent; insecticide; metabolite; plant metabolite
salicylamide salamide: a major impurity of hydrochlorothiazide; structure in first source	2.37	2	0	phenols; salicylamides	antirheumatic drug; non-narcotic analgesic
sanguinarine benzophenanthridine alkaloid : A specific group of isoquinoline alkaloids that occur only in higher plants and are constituents mainly of the Papaveraceae family.	2.02	1	0	alkaloid antibiotic; benzophenanthridine alkaloid; botanical anti-fungal agent
sb 202190 4-(4-fluorophenyl)-2-(4-hydroxyphenyl)-5-(4-pyridyl)imidazole: structure given in first source; inhibits p38 MAP kinase	2.02	1	0	imidazoles; organofluorine compound; phenols; pyridines	apoptosis inducer; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor
linsidomine linsidomine: RN given refers to parent cpd; structure	2	1	0	morpholines
sodium fluoride [no description available]	1.97	1	0	fluoride salt	mutagen
fluoroacetic acid fluoroacetic acid: N1 same as NM; RN given refers to parent cpd. fluoroacetic acid : A haloacetic acid that is acetic acid in which one of the methyl hydrogens is substituted by fluorine.	2.08	1	0	haloacetic acid; organofluorine compound	EC 4.2.1.3 (aconitate hydratase) inhibitor
vorinostat Vorinostat: A hydroxamic acid and anilide derivative that acts as a HISTONE DEACETYLASE inhibitor. It is used in the treatment of CUTANEOUS T-CELL LYMPHOMA and SEZARY SYNDROME.. vorinostat : A dicarboxylic acid diamide comprising suberic (octanedioic) acid coupled to aniline and hydroxylamine. A histone deacetylase inhibitor, it is marketed under the name Zolinza for the treatment of cutaneous T cell lymphoma (CTCL).	2.02	1	0	dicarboxylic acid diamide; hydroxamic acid	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor
sulfamethazine Sulfamethazine: A sulfanilamide anti-infective agent. It has a spectrum of antimicrobial action similar to other sulfonamides.. sulfamethazine : A sulfonamide consisting of pyrimidine with methyl substituents at the 4- and 6-positions and a 4-aminobenzenesulfonamido group at the 2-position.	2.39	2	0	pyrimidines; sulfonamide antibiotic; sulfonamide	antibacterial drug; antiinfective agent; antimicrobial agent; carcinogenic agent; drug allergen; EC 2.5.1.15 (dihydropteroate synthase) inhibitor; environmental contaminant; ligand; xenobiotic
sulfaphenazole Sulfaphenazole: A sulfonilamide anti-infective agent.. sulfaphenazole : A sulfonamide that is sulfanilamide in which the sulfonamide nitrogen is substituted by a 1-phenyl-1H-pyrazol-5-yl group. It is a selective inhibitor of cytochrome P450 (CYP) 2C9 isozyme, and antibacterial agent.	1.98	1	0	primary amino compound; pyrazoles; substituted aniline; sulfonamide antibiotic; sulfonamide	antibacterial drug; EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor; EC 1.14.13.67 (quinine 3-monooxygenase) inhibitor; P450 inhibitor
sulforaphane sulforaphane: from Cardaria draba L.. sulforaphane : An isothiocyanate having a 4-(methylsulfinyl)butyl group attached to the nitrogen.	4.06	14	0	isothiocyanate; sulfoxide	antineoplastic agent; antioxidant; EC 3.5.1.98 (histone deacetylase) inhibitor; plant metabolite
sulpiride Sulpiride: A dopamine D2-receptor antagonist. It has been used therapeutically as an antidepressant, antipsychotic, and as a digestive aid. (From Merck Index, 11th ed). sulpiride : A member of the class of benzamides obtained from formal condensation between the carboxy group of 2-methoxy-5-sulfamoylbenzoic acid and the primary amino group of (1-ethylpyrrolidin-2-yl)methylamine.	2.03	1	0	benzamides; N-alkylpyrrolidine; sulfonamide	antidepressant; antiemetic; antipsychotic agent; dopaminergic antagonist
1,4-bis(2-(3,5-dichloropyridyloxy))benzene 1,4-bis(2-(3,5-dichloropyridyloxy))benzene: potent phenobarbital-like inducer of microsomal monooxygenase activity; structure given in first source	2.41	2	0
tetraethylammonium Tetraethylammonium: A potassium-selective ion channel blocker. (From J Gen Phys 1994;104(1):173-90)	2.42	2	0	quaternary ammonium ion
thalidomide Thalidomide: A piperidinyl isoindole originally introduced as a non-barbiturate hypnotic, but withdrawn from the market due to teratogenic effects. It has been reintroduced and used for a number of immunological and inflammatory disorders. Thalidomide displays immunosuppressive and anti-angiogenic activity. It inhibits release of TUMOR NECROSIS FACTOR-ALPHA from monocytes, and modulates other cytokine action.. thalidomide : A racemate comprising equimolar amounts of R- and S-thalidomide.. 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione : A dicarboximide that is isoindole-1,3(2H)-dione in which the hydrogen attached to the nitrogen is substituted by a 2,6-dioxopiperidin-3-yl group.	4.85	4	0	phthalimides; piperidones
thiotepa Thiotepa: A very toxic alkylating antineoplastic agent also used as an insect sterilant. It causes skin, gastrointestinal, CNS, and bone marrow damage. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), thiotepa may reasonably be anticipated to be a carcinogen (Merck Index, 11th ed).	2	1	0	aziridines
tilorone Tilorone: An antiviral agent used as its hydrochloride. It is the first recognized synthetic, low-molecular-weight compound that is an orally active interferon inducer, and is also reported to have antineoplastic and anti-inflammatory actions.. tilorone : A member of the class of fluoren-9-ones that is 9H-fluoren-9-one which is substituted by a 2-(diethylamino)ethoxy group at positions 2 and 7. It is an interferon inducer and a selective alpha7 nicotinic acetylcholine receptor (alpha7 nAChR) agonist. Its hydrochloride salt is used as an antiviral drug.	1.96	1	0	aromatic ether; diether; fluoren-9-ones; tertiary amino compound	anti-inflammatory agent; antineoplastic agent; antiviral agent; interferon inducer; nicotinic acetylcholine receptor agonist
tiopronin Tiopronin: Sulfhydryl acylated derivative of GLYCINE.	2.38	2	0	N-acyl-amino acid
todralazine Todralazine: An antihypertensive agent with both central and peripheral action; it has some central nervous system depressant effects.	7.67	3	0	phthalazines
triclosan [no description available]	3.43	6	0	aromatic ether; dichlorobenzene; monochlorobenzenes; phenols	antibacterial agent; antimalarial; drug allergen; EC 1.3.1.9 [enoyl-[acyl-carrier-protein] reductase (NADH)] inhibitor; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; fungicide; persistent organic pollutant; xenobiotic
trifluoperazine [no description available]	1.99	1	0	N-alkylpiperazine; N-methylpiperazine; organofluorine compound; phenothiazines	antiemetic; calmodulin antagonist; dopaminergic antagonist; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor; EC 5.3.3.5 (cholestenol Delta-isomerase) inhibitor; phenothiazine antipsychotic drug
trifluralin Trifluralin: A microtubule-disrupting pre-emergence herbicide.. trifluralin : A substituted aniline that is N,N-dipropylaniline substituted by a nitro groups at positions 2 and 6 and a trifluoromethyl group at position 4. It is an agrochemical used as a pre-emergence herbicide.	7.39	2	0	(trifluoromethyl)benzenes; C-nitro compound; substituted aniline	agrochemical; environmental contaminant; herbicide; xenobiotic
troglitazone Troglitazone: A chroman and thiazolidinedione derivative that acts as a PEROXISOME PROLIFERATOR-ACTIVATED RECEPTORS (PPAR) agonist. It was formerly used in the treatment of TYPE 2 DIABETES MELLITUS, but has been withdrawn due to hepatotoxicity.	2.04	1	0	chromanes; thiazolidinone	anticoagulant; anticonvulsant; antineoplastic agent; antioxidant; EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor; ferroptosis inhibitor; hypoglycemic agent; platelet aggregation inhibitor; vasodilator agent
tyramine [no description available]	7.4	2	0	monoamine molecular messenger; primary amino compound; tyramines	EC 3.1.1.8 (cholinesterase) inhibitor; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter
urethane [no description available]	5.1	14	0	carbamate ester	fungal metabolite; mutagen
pirinixic acid pirinixic acid: structure	1.96	1	0	aryl sulfide; organochlorine compound; pyrimidines
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	7.71	3	0
zinc chloride zinc chloride: RN given refers to parent cpd. zinc dichloride : A compound of zinc and chloride ions in the ratio 1:2. It exists in four crystalline forms, in each of which the Zn(2+) ions are trigonal planar coordinated to four chloride ions.	2.01	1	0	inorganic chloride; zinc molecular entity	astringent; disinfectant; EC 5.3.3.5 (cholestenol Delta-isomerase) inhibitor; Lewis acid
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.	10.92	33	0	mitomycin	alkylating agent; antineoplastic agent
corticosterone [no description available]	3.47	8	0	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone	human metabolite; mouse metabolite
reserpine Reserpine: An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria. Reserpine inhibits the uptake of norepinephrine into storage vesicles resulting in depletion of catecholamines and serotonin from central and peripheral axon terminals. It has been used as an antihypertensive and an antipsychotic as well as a research tool, but its adverse effects limit its clinical use.. reserpine : An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria.	3.11	5	0	alkaloid ester; methyl ester; yohimban alkaloid	adrenergic uptake inhibitor; antihypertensive agent; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; environmental contaminant; first generation antipsychotic; plant metabolite; xenobiotic
sorbitol D-glucitol : The D-enantiomer of glucitol (also known as D-sorbitol).	2.41	1	0	glucitol	cathartic; Escherichia coli metabolite; food humectant; human metabolite; laxative; metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite; sweetening agent
alloxan Alloxan: Acidic compound formed by oxidation of URIC ACID. It is isolated as an efflorescent crystalline hydrate.. alloxan : A member of the class of pyrimidones, the structure of which is that of perhydropyrimidine substituted at C-2, -4, -5 and -6 by oxo groups.	7.57	2	0	pyrimidone	hyperglycemic agent; metabolite
thymidine [no description available]	4.11	16	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite
piperonyl butoxide [no description available]	2.7	3	0	benzodioxoles	pesticide synergist
triethylenemelamine Triethylenemelamine: Toxic alkylating agent used in industry; also as antineoplastic and research tool to produce chromosome aberrations and cancers.	2.37	2	0	1,3,5-triazines	alkylating agent; insect sterilant
thyroxine Thyroxine: The major hormone derived from the thyroid gland. Thyroxine is synthesized via the iodination of tyrosines (MONOIODOTYROSINE) and the coupling of iodotyrosines (DIIODOTYROSINE) in the THYROGLOBULIN. Thyroxine is released from thyroglobulin by proteolysis and secreted into the blood. Thyroxine is peripherally deiodinated to form TRIIODOTHYRONINE which exerts a broad spectrum of stimulatory effects on cell metabolism.. thyroxine : An iodothyronine compound having iodo substituents at the 3-, 3'-, 5- and 5'-positions.	2.37	2	0	2-halophenol; iodophenol; L-phenylalanine derivative; non-proteinogenic L-alpha-amino acid; thyroxine zwitterion; thyroxine	antithyroid drug; human metabolite; mouse metabolite; thyroid hormone
spironolactone Spironolactone: A potassium sparing diuretic that acts by antagonism of aldosterone in the distal renal tubules. It is used mainly in the treatment of refractory edema in patients with congestive heart failure, nephrotic syndrome, or hepatic cirrhosis. Its effects on the endocrine system are utilized in the treatments of hirsutism and acne but they can lead to adverse effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p827). spironolactone : A steroid lactone that is 17alpha-pregn-4-ene-21,17-carbolactone substituted by an oxo group at position 3 and an alpha-acetylsulfanyl group at position 7.	2.42	2	0	3-oxo-Delta(4) steroid; oxaspiro compound; steroid lactone; thioester	aldosterone antagonist; antihypertensive agent; diuretic; environmental contaminant; xenobiotic
estrone Hydroxyestrones: Estrone derivatives substituted with one or more hydroxyl groups in any position. They are important metabolites of estrone and other estrogens.	2.13	1	0	17-oxo steroid; 3-hydroxy steroid; phenolic steroid; phenols	antineoplastic agent; bone density conservation agent; estrogen; human metabolite; mouse metabolite
dehydroepiandrosterone Dehydroepiandrosterone: A major C19 steroid produced by the ADRENAL CORTEX. It is also produced in small quantities in the TESTIS and the OVARY. Dehydroepiandrosterone (DHEA) can be converted to TESTOSTERONE; ANDROSTENEDIONE; ESTRADIOL; and ESTRONE. Most of DHEA is sulfated (DEHYDROEPIANDROSTERONE SULFATE) before secretion.. dehydroepiandrosterone : An androstanoid that is androst-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 17. It is a naturally occurring steroid hormone produced by the adrenal glands.	2	1	0	17-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; androstanoid	androgen; human metabolite; mouse metabolite
1,2,5,6-dibenzanthracene 1,2,5,6-dibenzanthracene: RN given refers to parent cpd	6.17	25	0	ortho-fused polycyclic arene	mutagen
dichlororibofuranosylbenzimidazole Dichlororibofuranosylbenzimidazole: An RNA polymerase II transcriptional inhibitor. This compound terminates transcription prematurely by selective inhibition of RNA synthesis. It is used in research to study underlying mechanisms of cellular regulation.	1.96	1	0
n-hydroxy-2-aminofluorene N-hydroxy-2-aminofluorene: structure	1.97	1	0
hydroxyacetylaminofluorene Hydroxyacetylaminofluorene: A N-hydroxylated derivative of 2-ACETYLAMINOFLUORENE that has demonstrated carcinogenic action.	2.38	2	0	2-acetamidofluorenes
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.	7.63	81	0	2-acetamidofluorenes	antimitotic; carcinogenic agent; epitope; mutagen
idoxuridine [no description available]	1.96	1	0	organoiodine compound; pyrimidine 2'-deoxyribonucleoside	antiviral drug; DNA synthesis inhibitor
triiodothyronine Triiodothyronine: A T3 thyroid hormone normally synthesized and secreted by the thyroid gland in much smaller quantities than thyroxine (T4). Most T3 is derived from peripheral monodeiodination of T4 at the 5' position of the outer ring of the iodothyronine nucleus. The hormone finally delivered and used by the tissues is mainly T3.. 3,3',5-triiodo-L-thyronine : An iodothyronine compound having iodo substituents at the 3-, 3'- and 5-positions. Although some is produced in the thyroid, most of the 3,3',5-triiodo-L-thyronine in the body is generated by mono-deiodination of L-thyroxine in the peripheral tissues. Its metabolic activity is about 3 to 5 times that of L-thyroxine. The sodium salt is used in the treatment of hypothyroidism.	2.7	3	0	2-halophenol; amino acid zwitterion; iodophenol; iodothyronine	human metabolite; mouse metabolite; thyroid hormone
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.	9.83	34	0	nitrosamine	carcinogenic agent; hepatotoxic agent; mutagen
methyldimethylaminoazobenzene Methyldimethylaminoazobenzene: A very potent liver carcinogen.. 3-methyl-4'-dimethylaminoazobenzene : A member of the class of azobenzenes that is azobenzene in which one of the phenyl groups is substituted at position 3 by a methyl group, while the other is substituted at position 4 by a dimethylamino group. It is a potent liver carcinogen.	2.66	3	0
isoflurophate Isoflurophate: A di-isopropyl-fluorophosphate which is an irreversible cholinesterase inhibitor used to investigate the NERVOUS SYSTEM.	1.97	1	0	dialkyl phosphate
dipropylenetriame N-(3-aminopropyl)-1,3-propanediamine: structure in first source	1.96	1	0	polyazaalkane	algal metabolite; plant metabolite
carbon tetrachloride Carbon Tetrachloride: A solvent for oils, fats, lacquers, varnishes, rubber waxes, and resins, and a starting material in the manufacturing of organic compounds. Poisoning by inhalation, ingestion or skin absorption is possible and may be fatal. (Merck Index, 11th ed). tetrachloromethane : A chlorocarbon that is methane in which all the hydrogens have been replaced by chloro groups.	8.59	9	0	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
alanine Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.	2.39	2	0	alanine zwitterion; alanine; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid	EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor; fundamental metabolite
serine Serine: A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids.. serine : An alpha-amino acid that is alanine substituted at position 3 by a hydroxy group.	7.44	2	0	L-alpha-amino acid; proteinogenic amino acid; serine family amino acid; serine zwitterion; serine	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
benz(a)anthracene benz(a)anthracene: 4 fused rings of which one is angular in contrast to the linear NAPHTHACENES. tetraphene : An angular ortho-fused polycyclic arene consisting of four fused benzene rings.	14.04	84	0	ortho-fused polycyclic arene; tetraphenes
4-nitroquinoline-1-oxide 4-nitroquinoline N-oxide : A quinoline N-oxide carrying a nitro substituent at position 4.	6.73	45	0	C-nitro compound; quinoline N-oxide	carcinogenic agent
chloramphenicol Amphenicol: Chloramphenicol and its derivatives.	2.21	1	0	C-nitro compound; carboxamide; diol; organochlorine compound	antibacterial drug; antimicrobial agent; Escherichia coli metabolite; geroprotector; Mycoplasma genitalium metabolite; protein synthesis inhibitor
glutamine Glutamine: A non-essential amino acid present abundantly throughout the body and is involved in many metabolic processes. It is synthesized from GLUTAMIC ACID and AMMONIA. It is the principal carrier of NITROGEN in the body and is an important energy source for many cells.. L-glutamine : An optically active form of glutamine having L-configuration.. glutamine : An alpha-amino acid that consists of butyric acid bearing an amino substituent at position 2 and a carbamoyl substituent at position 4.	2.08	1	0	amino acid zwitterion; glutamine family amino acid; glutamine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	EC 1.14.13.39 (nitric oxide synthase) inhibitor; Escherichia coli metabolite; human metabolite; metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
lysine Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.	2.73	3	0	aspartate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; lysine; organic molecular entity; proteinogenic amino acid	algal metabolite; anticonvulsant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
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.	2.01	1	0	alkenyl isothiocyanate; isothiocyanate	antimicrobial agent; antineoplastic agent; apoptosis inducer; lachrymator; metabolite
dimazine dimazine: RN given refers to parent cpd. 1,1-dimethylhydrazine : A member of the class of hydrazines that is hydrazine substituted by two methyl groups at position 1.	2.39	2	0	hydrazines	carcinogenic agent; fuel; teratogenic agent
sucrose Saccharum: A plant genus of the family POACEAE widely cultivated in the tropics for the sweet cane that is processed into sugar.	2.92	4	0	glycosyl glycoside	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; sweetening agent
ethinyl estradiol Ethinyl Estradiol: A semisynthetic alkylated ESTRADIOL with a 17-alpha-ethinyl substitution. It has high estrogenic potency when administered orally, and is often used as the estrogenic component in ORAL CONTRACEPTIVES.. 17alpha-ethynylestradiol : A 3-hydroxy steroid that is estradiol substituted by a ethynyl group at position 17. It is a xenoestrogen synthesized from estradiol and has been shown to exhibit high estrogenic potency on oral administration.	4.05	14	0	17-hydroxy steroid; 3-hydroxy steroid; terminal acetylenic compound	xenoestrogen
chlordan Chlordan: A highly poisonous organochlorine insecticide. The EPA has cancelled registrations of pesticides containing this compound with the exception of its use through subsurface ground insertion for termite control and the dipping of roots or tops of non-food plants. (From Merck Index, 11th ed)	3.46	2	0	cyclodiene organochlorine insecticide	GABA-gated chloride channel antagonist; persistent organic pollutant
testosterone propionate Testosterone Propionate: An ester of TESTOSTERONE with a propionate substitution at the 17-beta position.. androgen : A sex hormone that stimulates or controls the development and maintenance of masculine characteristics in vertebrates by binding to androgen receptors.	2.04	1	0	steroid ester
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.	11.04	227	0	ortho-fused polycyclic arene; tetraphenes	carcinogenic agent
aminopyrine Aminopyrine: A pyrazolone with analgesic, anti-inflammatory, and antipyretic properties but has risk of AGRANULOCYTOSIS. A breath test with 13C-labeled aminopyrine has been used as a non-invasive measure of CYTOCHROME P-450 metabolic activity in LIVER FUNCTION TESTS.. aminophenazone : A pyrazolone that is 1,2-dihydro-3H-pyrazol-3-one substituted by a dimethylamino group at position 4, methyl groups at positions 1 and 5 and a phenyl group at position 2. It exhibits analgesic, anti-inflammatory, and antipyretic properties.	3.57	9	0	pyrazolone; tertiary amino compound	antipyretic; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
adenosine diphosphate Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.	4.19	5	0	adenosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	fundamental metabolite; human metabolite
2,3,4,6-tetrachlorophenol 2,3,4,6-tetrachlorophenol: RN given refers to parent cpd; see also record for tetrachlorophenol with locants for chloro groups not specified. 2,3,4,6-tetrachlorophenol : A tetrachlorophenol in which the chlorines are located at positions 2, 3, 4, and 6.	2.68	3	0	tetrachlorophenol	xenobiotic metabolite
bromodeoxyuridine Bromodeoxyuridine: A nucleoside that substitutes for thymidine in DNA and thus acts as an antimetabolite. It causes breaks in chromosomes and has been proposed as an antiviral and antineoplastic agent. It has been given orphan drug status for use in the treatment of primary brain tumors.	3.36	7	0	pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent
galactose galactopyranose : The pyranose form of galactose.	1.99	1	0	D-galactose; galactopyranose	Escherichia coli metabolite; mouse metabolite
carbostyril Quinolones: A group of derivatives of naphthyridine carboxylic acid, quinoline carboxylic acid, or NALIDIXIC ACID.. quinolin-2(1H)-one : A quinolone that is 1,2-dihydroquinoline substituted by an oxo group at position 2.	2.93	4	0	monohydroxyquinoline; quinolone	bacterial xenobiotic metabolite
n-nitrosomorpholine N-nitrosomorpholine : A nitrosamine that is morpholine in which the hydrogen attached to the nitrogen is replaced by a nitroso group. A carcinogen and mutagen, it is found in snuff tobacco.	2.01	1	0	nitrosamine	carcinogenic agent; mutagen
levodopa Levodopa: The naturally occurring form of DIHYDROXYPHENYLALANINE and the immediate precursor of DOPAMINE. Unlike dopamine itself, it can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to DOPAMINE. It is used for the treatment of PARKINSONIAN DISORDERS and is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system.. L-dopa : An optically active form of dopa having L-configuration. Used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease	2.03	1	0	amino acid zwitterion; dopa; L-tyrosine derivative; non-proteinogenic L-alpha-amino acid	allelochemical; antidyskinesia agent; antiparkinson drug; dopaminergic agent; hapten; human metabolite; mouse metabolite; neurotoxin; plant growth retardant; plant metabolite; prodrug
edetic acid Edetic Acid: A chelating agent that sequesters a variety of polyvalent cations such as CALCIUM. It is used in pharmaceutical manufacturing and as a food additive.	2.68	3	0	ethylenediamine derivative; polyamino carboxylic acid; tetracarboxylic acid	anticoagulant; antidote; chelator; copper chelator; geroprotector
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.	2.42	2	0
p-dimethylaminoazobenzene p-Dimethylaminoazobenzene: A reagent used mainly to induce experimental liver cancer. According to the Fourth Annual Report on Carcinogens (NTP 85-002, p. 89) published in 1985, this compound may reasonably be anticipated to be a carcinogen. (Merck, 11th ed)	2.66	3	0	azobenzenes
phenylethyl alcohol Phenylethyl Alcohol: An antimicrobial, antiseptic, and disinfectant that is used also as an aromatic essence and preservative in pharmaceutics and perfumery.. 2-phenylethanol : A primary alcohol that is ethanol substituted by a phenyl group at position 2.	2.08	1	0	benzenes; primary alcohol	Aspergillus metabolite; fragrance; plant growth retardant; plant metabolite; Saccharomyces cerevisiae metabolite
tyrosine Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.	2.96	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
methoxamine Methoxamine: An alpha-1 adrenergic agonist that causes prolonged peripheral VASOCONSTRICTION.. methoxamine : An amphetamine in which the parent 1-phenylpropan-2-amine skeleton is substituted at position 1 with an hydroxy group and the phenyl ring is 2- and 5-substituted with methoxy groups. It is an antihypotensive agent (pressor), an agonist acting directly at alpha-adrenoceptors with selectivity for the alpha-1 adrenoceptor subtype similar to phenylephrine .	1.98	1	0	amphetamines	alpha-adrenergic agonist; antihypotensive agent
adenosine monophosphate Adenosine Monophosphate: Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position.	2.04	1	0	adenosine 5'-phosphate; purine ribonucleoside 5'-monophosphate	adenosine A1 receptor agonist; cofactor; EC 3.1.3.1 (alkaline phosphatase) inhibitor; EC 3.1.3.11 (fructose-bisphosphatase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
methylene blue Methylene Blue: A compound consisting of dark green crystals or crystalline powder, having a bronze-like luster. Solutions in water or alcohol have a deep blue color. Methylene blue is used as a bacteriologic stain and as an indicator. It inhibits GUANYLATE CYCLASE, and has been used to treat cyanide poisoning and to lower levels of METHEMOGLOBIN.. methylene blue : An organic chloride salt having 3,7-bis(dimethylamino)phenothiazin-5-ium as the counterion. A commonly used dye that also exhibits antioxidant, antimalarial, antidepressant and cardioprotective properties.	2.72	3	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
zoxazolamine Zoxazolamine: A uricosuric and muscle relaxant. Zoxazolamine acts centrally as a muscle relaxant, but the mechanism of its action is not understood.	3.47	2	0	benzoxazole
leucine Leucine: An essential branched-chain amino acid important for hemoglobin formation.. leucine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isobutyl group.	5.41	4	1	amino acid zwitterion; L-alpha-amino acid; leucine; proteinogenic amino acid; pyruvate family amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
ethyl methanesulfonate Ethyl Methanesulfonate: An antineoplastic agent with alkylating properties. It also acts as a mutagen by damaging DNA and is used experimentally for that effect.. ethyl methanesulfonate : A methanesulfonate ester resulting from the formal condensation of methanesulfonic acid with ethanol.	12.38	33	4	methanesulfonate ester	alkylating agent; antineoplastic agent; carcinogenic agent; genotoxin; mutagen; teratogenic agent
aniline [no description available]	8.47	8	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.	5.17	48	0	nitrosamine	geroprotector; mutagen
carbaryl Carbaryl: A carbamate insecticide and parasiticide. It is a potent anticholinesterase agent belonging to the carbamate group of reversible cholinesterase inhibitors. It has a particularly low toxicity from dermal absorption and is used for control of head lice in some countries.. carbaryl : A carbamate ester obtained by the formal condensation of 1-naphthol with methylcarbamic acid.	2.88	4	0	carbamate ester; naphthalenes	acaricide; agrochemical; carbamate insecticide; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; plant growth retardant
methionine Methionine: A sulfur-containing essential L-amino acid that is important in many body functions.. methionine : A sulfur-containing amino acid that is butyric acid bearing an amino substituent at position 2 and a methylthio substituent at position 4.	11.36	7	1	aspartate family amino acid; L-alpha-amino acid; methionine zwitterion; methionine; proteinogenic amino acid	antidote to paracetamol poisoning; human metabolite; micronutrient; mouse metabolite; nutraceutical
1,2-dipalmitoylphosphatidylcholine 1,2-Dipalmitoylphosphatidylcholine: Synthetic phospholipid used in liposomes and lipid bilayers to study biological membranes. It is also a major constituent of PULMONARY SURFACTANTS.	3.32	6	0
phenylalanine Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.	2.51	2	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; phenylalanine; proteinogenic amino acid	algal metabolite; EC 3.1.3.1 (alkaline phosphatase) inhibitor; Escherichia coli metabolite; human xenobiotic metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
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.	6.4	7	1	alkaloid; colchicine	anti-inflammatory agent; gout suppressant; mutagen
uracil mustard Uracil Mustard: Nitrogen mustard derivative of URACIL. It is a alkylating antineoplastic agent that is used in lymphatic malignancies, and causes mainly gastrointestinal and bone marrow damage.	1.96	1	0	aminouracil; nitrogen mustard
cycloheximide Cycloheximide: Antibiotic substance isolated from streptomycin-producing strains of Streptomyces griseus. It acts by inhibiting elongation during protein synthesis.. cycloheximide : A dicarboximide that is 4-(2-hydroxyethyl)piperidine-2,6-dione in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 3,5-dimethyl-2-oxocyclohexyl group. It is an antibiotic produced by the bacterium Streptomyces griseus.	4.13	16	0	antibiotic fungicide; cyclic ketone; dicarboximide; piperidine antibiotic; piperidones; secondary alcohol	anticoronaviral agent; bacterial metabolite; ferroptosis inhibitor; neuroprotective agent; protein synthesis inhibitor
egtazic acid Egtazic Acid: A chelating agent relatively more specific for calcium and less toxic than EDETIC ACID.. ethylene glycol bis(2-aminoethyl)tetraacetic acid : A diether that is ethylene glycol in which the hydrogens of the hydroxy groups have been replaced by 2-[bis(carboxymethyl)amino]ethyl group respectively.	2.44	2	0	diether; tertiary amino compound; tetracarboxylic acid	chelator
chloroform Chloroform: A commonly used laboratory solvent. It was previously used as an anesthetic, but was banned from use in the U.S. due to its suspected carcinogenicity.. chloroform : A one-carbon compound that is methane in which three of the hydrogens are replaced by chlorines.	3.37	7	0	chloromethanes; one-carbon compound	carcinogenic agent; central nervous system drug; inhalation anaesthetic; non-polar solvent; refrigerant
fluocinolone acetonide Fluocinolone Acetonide: A glucocorticoid derivative used topically in the treatment of various skin disorders. It is usually employed as a cream, gel, lotion, or ointment. It has also been used topically in the treatment of inflammatory eye, ear, and nose disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p732). fluocinolone acetonide : A fluorinated steroid that is flunisolide in which the hydrogen at position 9 is replaced by fluorine. A corticosteroid with glucocorticoid activity, it is used (both as the anhydrous form and as the dihydrate) in creams, gels and ointments for the treatment of various skin disorders.	1.96	1	0	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; cyclic ketal; fluorinated steroid; glucocorticoid; organic heteropentacyclic compound; primary alpha-hydroxy ketone	anti-inflammatory drug; antipruritic drug
gliotoxin Gliotoxin: A fungal toxin produced by various species of Trichoderma, Gladiocladium fimbriatum, Aspergillus fumigatus, and Penicillium. It is used as an immunosuppressive agent.. gliotoxin : A pyrazinoindole with a disulfide bridge spanning a dioxo-substituted pyrazine ring; mycotoxin produced by several species of fungi.	2.04	1	0	dipeptide; organic disulfide; organic heterotetracyclic compound; pyrazinoindole	antifungal agent; EC 2.5.1.58 (protein farnesyltransferase) inhibitor; immunosuppressive agent; mycotoxin; proteasome inhibitor
dimethylformamide Dimethylformamide: A formamide in which the amino hydrogens are replaced by methyl groups.. N,N-dimethylformamide : A member of the class of formamides that is formamide in which the amino hydrogens are replaced by methyl groups.	3.02	4	0	formamides; volatile organic compound	geroprotector; hepatotoxic agent; polar aprotic solvent
norethindrone Norethindrone: A synthetic progestational hormone with actions similar to those of PROGESTERONE but functioning as a more potent inhibitor of ovulation. It has weak estrogenic and androgenic properties. The hormone has been used in treating amenorrhea, functional uterine bleeding, endometriosis, and for CONTRACEPTION.. norethisterone : A 17beta-hydroxy steroid that is testosterone in which the hydrogen at position 17 is replaced by an ethynyl group and in which the methyl group attached to position 10 is replaced by hydrogen.	1.96	1	0	17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; terminal acetylenic compound; tertiary alcohol	progestin; synthetic oral contraceptive
mannitol [no description available]	2.91	4	0	mannitol	allergen; antiglaucoma drug; compatible osmolytes; Escherichia coli metabolite; food anticaking agent; food bulking agent; food humectant; food stabiliser; food thickening agent; hapten; metabolite; osmotic diuretic; sweetening agent
cytarabine [no description available]	3.49	8	0	beta-D-arabinoside; monosaccharide derivative; pyrimidine nucleoside	antimetabolite; antineoplastic agent; antiviral agent; immunosuppressive agent
ornithine Ornithine: An amino acid produced in the urea cycle by the splitting off of urea from arginine.. ornithine : An alpha-amino acid that is pentanoic acid bearing two amino substituents at positions 2 and 5.	2.38	2	0	non-proteinogenic L-alpha-amino acid; ornithine	algal metabolite; hepatoprotective agent; mouse metabolite
dinitrofluorobenzene Dinitrofluorobenzene: Irritants and reagents for labeling terminal amino acid groups.. 1-fluoro-2,4-dinitrobenzene : The organofluorine compound that is benzene with a fluoro substituent at the 1-position and two nitro substituents in the 2- and 4-positions.	1.97	1	0	C-nitro compound; organofluorine compound	agrochemical; allergen; chromatographic reagent; EC 2.7.3.2 (creatine kinase) inhibitor; protein-sequencing agent; spectrophotometric reagent
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.	2.92	4	0	amino acid zwitterion; histidine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
n-pentanol n-pentanol: RN given refers to parent cpd. pentan-1-ol : A short-chain primary fatty alcohol that is pentane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It has been isolated from Melicope ptelefolia.	2.02	1	0	pentanol; short-chain primary fatty alcohol	human metabolite; plant metabolite
1,1,1-trichloroethane Trichloroethanes: Chlorinated ethanes which are used extensively as industrial solvents. They have been utilized in numerous home-use products including spot remover preparations and inhalant decongestant sprays. These compounds cause central nervous system and cardiovascular depression and are hepatotoxic. Include 1,1,1- and 1,1,2-isomers.. 1,1,1-trichloroethane : A member of the class of chloroethanes carrying three chloro substituents at position 1.	2.04	1	0	chloroethanes	polar solvent
valine Valine: A branched-chain essential amino acid that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway.. valine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isopropyl group.. L-valine : The L-enantiomer of valine.	2.39	2	0	L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid; valine	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
mestranol [no description available]	1.96	1	0	17beta-hydroxy steroid; aromatic ether; terminal acetylenic compound	prodrug; xenoestrogen
alizarin [no description available]	2.01	1	0	dihydroxyanthraquinone	chromophore; dye; plant metabolite
tryptophan Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3.	2.44	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
isoleucine Isoleucine: An essential branched-chain aliphatic amino acid found in many proteins. It is an isomer of LEUCINE. It is important in hemoglobin synthesis and regulation of blood sugar and energy levels.. isoleucine : A 2-amino-3-methylpentanoic acid having either (2R,3R)- or (2S,3S)-configuration.. L-isoleucine : The L-enantiomer of isoleucine.	1.99	1	0	aspartate family amino acid; isoleucine; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
arginine Arginine: An essential amino acid that is physiologically active in the L-form.. arginine : An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group.	5.24	3	1	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
acetylene [no description available]	2.48	2	0	alkyne; gas molecular entity; terminal acetylenic compound
propane Propane: A three carbon alkane with the formula H3CCH2CH3.	2.91	4	0	alkane; gas molecular entity	food propellant
ethyl chloride Ethyl Chloride: A gas that condenses under slight pressure. Because of its low boiling point ethyl chloride sprayed on skin produces an intense cold by evaporation. Cold blocks nerve conduction. Ethyl chloride has been used in surgery but is primarily used to relieve local pain in sports medicine.. chloroethane : The simplest and least toxic member of the class of chloroethanes, that is ethane in which a single hydrogen is substituted by a chlorine. A colourless gas at room temperature and pressure (boiling point 12degreeC), it is used as a mild topical anaesthetic to numb the skin prior to ear piercing, skin biopsies, etc., and is also used in the treatment of sports injuries. It was formerly used in the production of tetraethyllead.	2.04	1	0	chloroethanes	antipruritic drug; inhalation anaesthetic; local anaesthetic
vinyl chloride Vinyl Chloride: A gas that has been used as an aerosol propellant and is the starting material for polyvinyl resins. Toxicity studies have shown various adverse effects, particularly the occurrence of liver neoplasms.. chloroethene : A monohaloethene that is ethene in which one of the hydrogens has been replaced by a chloro group.	2.38	2	0	chloroethenes; gas molecular entity; monohaloethene	carcinogenic agent
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.	8.29	6	0	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
methylene chloride Methylene Chloride: A chlorinated hydrocarbon that has been used as an inhalation anesthetic and acts as a narcotic in high concentrations. Its primary use is as a solvent in manufacturing and food technology.. dichloromethane : A member of the class of chloromethanes that is methane in which two of the hydrogens have been replaced by chlorine. A dense, non-flammible colourless liquid at room temperature (b.p. 40degreeC, d = 1.33) which is immiscible with water, it is widely used as a solvent, a paint stripper, and for the removal of caffeine from coffee and tea.	3.49	8	0	chloromethanes; volatile organic compound	carcinogenic agent; polar aprotic solvent; refrigerant
carbon disulfide Carbon Disulfide: A colorless, flammable, poisonous liquid, CS2. It is used as a solvent, and is a counterirritant and has local anesthetic properties but is not used as such. It is highly toxic with pronounced CNS, hematologic, and dermatologic effects.	1.97	1	0	one-carbon compound; organosulfur compound
ethylene oxide Ethylene Oxide: A colorless and flammable gas at room temperature and pressure. Ethylene oxide is a bactericidal, fungicidal, and sporicidal disinfectant. It is effective against most micro-organisms, including viruses. It is used as a fumigant for foodstuffs and textiles and as an agent for the gaseous sterilization of heat-labile pharmaceutical and surgical materials. (From Reynolds, Martindale The Extra Pharmacopoeia, 30th ed, p794). oxirane : A saturated organic heteromonocyclic parent that is a three-membered heterocycle of two carbon atoms and one oxygen atom.	2.37	2	0	gas molecular entity; oxacycle; saturated organic heteromonocyclic parent	allergen; mouse metabolite; mutagen
2-bromopropane 2-bromopropane: used as a substitute for freon	2.01	1	0
bromodichloromethane bromodichloromethane: RN given refers to parent cpd. bromodichloromethane : A halomethane that is dichloromethane in which oneof the hydrogens has been replaced by a bromine atom. It occurs as a contaminant in drinking water.	1.98	1	0	halomethane	environmental contaminant; reagent
vinylidene chloride vinylidene chloride: potent hepatotoxin. 1,1-dichloroethene : A member of the class of chloroethenes that is ethene in which both of the hydrogens attached to one of the carbons are replaced by chlorines.	3.09	1	0	chloroethenes	carcinogenic agent; mouse metabolite; mutagen
propyleneimine [no description available]	2.38	2	0	aziridines
tert-butyl alcohol tert-Butyl Alcohol: An isomer of butanol that contains a tertiary butyl group that consists of three methyl groups, each separately attached to a central (tertiary) carbon.. tert-butanol : A tertiary alcohol alcohol that is isobutane substituted by a hydroxy group at position 2.	2.42	2	0	tertiary alcohol	human xenobiotic metabolite
trichlorofluoromethane trichlorofluoromethane: refrigerant, aerosol propellant; RN given refers to parent cpd; structure. trichlorofluoromethane : A one-carbon compound that is methane in which the hydrogens have been replaced by three chlorine and one fluorine atom.	2.04	1	0	chlorofluorocarbon; halomethane	environmental contaminant; NMR chemical shift reference compound; NMR solvent; refrigerant
methanesulfonic acid [no description available]	2.03	1	0	alkanesulfonic acid; one-carbon compound	Escherichia coli metabolite
trifluoroethanol Trifluoroethanol: A non-aqueous co-solvent that serves as tool to study protein folding. It is also used in various pharmaceutical, chemical and engineering applications.	2.03	1	0	fluoroalcohol
tert-butylhydroperoxide tert-Butylhydroperoxide: A direct-acting oxidative stress-inducing agent used to examine the effects of oxidant stress on Ca(2+)-dependent signal transduction in vascular endothelial cells. It is also used as a catalyst in polymerization reactions and to introduce peroxy groups into organic molecules.. tert-butyl hydroperoxide : An alkyl hydroperoxide in which the alkyl group is tert-butyl. It is widely used in a variety of oxidation processes.	3.27	6	0	alkyl hydroperoxide	antibacterial agent; oxidising agent
pentachloroethane [no description available]	2.04	1	0	chloroethanes	non-polar solvent
trichloroacetic acid Trichloroacetic Acid: A strong acid used as a protein precipitant in clinical chemistry and also as a caustic for removing warts.. trichloroacetic acid : A monocarboxylic acid that is acetic acid in which all three methyl hydrogens are substituted by chlorine.	1.96	1	0	monocarboxylic acid; organochlorine compound	carcinogenic agent; metabolite; mouse metabolite
trifluoroacetic acid Trifluoroacetic Acid: A very strong halogenated derivative of acetic acid. It is used in acid catalyzed reactions, especially those where an ester is cleaved in peptide synthesis.. trifluoroacetic acid : A monocarboxylic acid that is the trifluoro derivative of acetic acid.	1.96	1	0	fluoroalkanoic acid	human xenobiotic metabolite; NMR chemical shift reference compound; reagent
gibberellic acid gibberellic acid: RN given refers to (1alpha,2beta,4aalpha,4bbeta,10beta)-isomer; structure. gibberellin A3 : A C19-gibberellin that is a pentacyclic diterpenoid responsible for promoting growth and elongation of cells in plants. Initially identified in Gibberella fujikuroi,it differs from gibberellin A1 in the presence of a double bond between C-3 and C-4.	2.03	1	0	C19-gibberellin; gibberellin monocarboxylic acid; lactone; organic heteropentacyclic compound	mouse metabolite; plant metabolite
phencyclidine Phencyclidine: A hallucinogen formerly used as a veterinary anesthetic, and briefly as a general anesthetic for humans. Phencyclidine is similar to KETAMINE in structure and in many of its effects. Like ketamine, it can produce a dissociative state. It exerts its pharmacological action through inhibition of NMDA receptors (RECEPTORS, N-METHYL-D-ASPARTATE). As a drug of abuse, it is known as PCP and Angel Dust.. phencyclidine : A member of the class of piperidines that is piperidine in which the nitrogen is substituted with a 1-phenylcyclohexyl group. Formerly used as an anaesthetic agent, it exhibits both hallucinogenic and neurotoxic effects.	8.08	43	1	benzenes; piperidines	anaesthetic; neurotoxin; NMDA receptor antagonist; psychotropic drug
isopentane [no description available]	2.04	1	0	alkane	refrigerant
isoprene isoprene: used in manufacture of ''synthetic'' rubber, butyl rubber; copolymer in production of elastomers; structure. isoprene : A hemiterpene with the formula CH2=C(CH3)CH=CH2; the monomer of natural rubber and a common structure motif to the isoprenoids, a large class of other naturally occurring compounds.	3.5	8	0	alkadiene; hemiterpene; volatile organic compound	plant metabolite
methylethyl ketone methylethyl ketone: solvent; colorless synthetic resins, smokeless powders; may be irritating to eyes, mucous membranes; may be toxic in high concentrations; structure. butanone : Any ketone that is butane substituted by an oxo group at unspecified position.. butan-2-one : A dialkyl ketone that is a four-carbon ketone carrying a single keto- group at position C-2.	2.15	1	0	butanone; dialkyl ketone; methyl ketone; volatile organic compound	bacterial metabolite; polar aprotic solvent
chloroacetone [no description available]	1.93	1	0	alpha-chloroketone
trichloroethylene Trichloroethylene: A highly volatile inhalation anesthetic used mainly in short surgical procedures where light anesthesia with good analgesia is required. It is also used as an industrial solvent. Prolonged exposure to high concentrations of the vapor can lead to cardiotoxicity and neurological impairment.. triol : A chemical compound containing three hydroxy groups.	7.92	4	0	chloroethenes	inhalation anaesthetic; mouse metabolite
acrylamide [no description available]	8.6	9	0	acrylamides; N-acylammonia; primary carboxamide	alkylating agent; carcinogenic agent; Maillard reaction product; mutagen; neurotoxin
peracetic acid Peracetic Acid: A liquid that functions as a strong oxidizing agent. It has an acrid odor and is used as a disinfectant.. peracetic acid : A peroxy acid that is acetic acid in which the OH group is substituted by a hydroperoxy group. It is a versatile oxidising agent that is used as a disinfectant.	2.44	2	0	a peroxy acid	disinfectant; oxidising agent
1,1,2,2-tetrachloroethane 1,1,2,2-tetrachloroethane: see also record for tetrachloroethane. 1,1,2,2-tetrachloroethane : A member of the class of chloroethanes that is ethane substituted by chloro groups at positions 1, 1, 2 and 2.	2.04	1	0	chloroethanes
pantothenic acid Pantothenic Acid: A butyryl-beta-alanine that can also be viewed as pantoic acid complexed with BETA ALANINE. It is incorporated into COENZYME A and protects cells against peroxidative damage by increasing the level of GLUTATHIONE.. pantothenic acid : A member of the class of pantothenic acids that is an amide formed from pantoic acid and beta-alanine.. vitamin B5 : Any member of a group of vitamers that belong to the chemical structural class called pantothenic acids that exhibit biological activity against vitamin B5 deficiency. Deficiency of vitamin B5 is rare due to its widespread distribution in whole grain cereals, legumes and meat. Symptoms associated with vitamin B5 deficiency are difficult to asses since they are subtle and resemble those of other B vitamin deficiencies. The vitamers include (R)-pantothenic acid and its ionized and salt forms.. (R)-pantothenate : A pantothenate that is the conjugate base of (R)-pantothenic acid, obtained by deprotonation of the carboxy group.. (R)-pantothenic acid : A pantothenic acid having R-configuration.	2.04	1	0	pantothenic acid; vitamin B5	antidote to curare poisoning; geroprotector; human blood serum metabolite
tetrabromobisphenol a tetrabromobisphenol A: a brominated flame retardant. 3,3',5,5'-tetrabromobisphenol A : A bromobisphenol that is 4,4'-methanediyldiphenol in which the methylene hydrogens are replaced by two methyl groups and the phenyl rings are substituted by bromo groups at positions 2, 2', 6 and 6'. It is a brominated flame retardant.	7.1	1	0	brominated flame retardant; bromobisphenol
bisphenol a 4,4'-isopropylidene diphenol: stimulates proliferative responses and cytokine productions of murine spleen cells and thymus cells in vitro. bisphenol : By usage, the methylenediphenols, HOC6H4CH2C6H4OH, commonly p,p-methylenediphenol, and their substitution products (generally derived from condensation of two equivalent amounts of a phenol with an aldehyde or ketone). The term also includes analogues in the the methylene (or substituted methylene) group has been replaced by a heteroatom.. bisphenol A : A bisphenol that is 4,4'-methanediyldiphenol in which the methylene hydrogens are replaced by two methyl groups.	7.37	18	1	bisphenol	endocrine disruptor; environmental contaminant; xenobiotic; xenoestrogen
bis(4-hydroxyphenyl)sulfone bis(4-hydroxyphenyl)sulfone: structure and RN in first source. 4,4'-sulfonyldiphenol : A sulfone that is diphenyl sulfone in which both of the para hydrogens have been replaced by hydroxy groups.	2.17	1	0	bisphenol; sulfone	endocrine disruptor; metabolite
cumene hydroperoxide cumene hydroperoxide: RN given refers to parent cpd. cumene hydroperoxide : A peroxol that is cumene in which the alpha-hydrogen is replaced by a hydroperoxy group.	3.36	7	0	peroxol	environmental contaminant; Mycoplasma genitalium metabolite; oxidising agent
methylmethacrylate Methylmethacrylate: The methyl ester of methacrylic acid. It polymerizes easily to form POLYMETHYL METHACRYLATE. It is used as a bone cement.. methyl methacrylate : An enoate ester having methacrylic acid as the carboxylic acid component and methanol as the alcohol component.	1.99	1	0	enoate ester; methyl ester	allergen; polymerisation monomer
musk ketone musk ketone: increases activity of glutathione S-transferase and thus may prove to be useful cancer chemoprotectant	7	1	0	aromatic ketone
visnagin visnagin: from Musineon divaricatum. visnagin : A furanochromone that is furo[3,2-g]chromen-5-one which is substituted at positions 4 and 7 by methoxy and methyl groups, respectively. Found in the toothpick-plant, Ammi visnaga.	1.99	1	0	aromatic ether; furanochromone; polyketide	anti-inflammatory agent; antihypertensive agent; EC 1.1.1.37 (malate dehydrogenase) inhibitor; phytotoxin; plant metabolite; vasodilator agent
acenaphthene [no description available]	2.43	2	0	acenaphthenes
skatole [no description available]	3.52	2	0	methylindole	human metabolite; mammalian metabolite
rotenone Derris: A plant genus of the family FABACEAE. The root is a source of rotenoids (ROTENONE) and flavonoids. Some species of Pongamia have been reclassified to this genus and some to MILLETTIA. Some species of Deguelia have been reclassified to this genus.. rotenoid : Members of the class of tetrahydrochromenochromene that consists of a cis-fused tetrahydrochromeno[3,4-b]chromene skeleton and its substituted derivatives. The term was originally restricted to natural products, but is now also used to describe semi-synthetic and fully synthetic compounds.	2.97	4	0	organic heteropentacyclic compound; rotenones	antineoplastic agent; metabolite; mitochondrial NADH:ubiquinone reductase inhibitor; phytogenic insecticide; piscicide; toxin
7,8-dimethyl-10-[(2R,3R,4S)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4-dione [no description available]	2.04	1	0	flavin
9,10-phenanthrenequinone 9,10-phenanthrenequinone: structure	2.15	1	0	phenanthrenes
2,6-dihydroxyanthraquinone 2,6-dihydroxyanthraquinone: structure given in first source. anthraflavic acid : A dihydroxyanthraquinone that is anthracene substituted by hydroxy groups at C-3 and C-7 and oxo groups at C-9 and C-10.	2.37	2	0	dihydroxyanthraquinone	antimutagen; plant metabolite
diquat Diquat: A contact herbicide used also to produce desiccation and defoliation. (From Merck Index, 11th ed). diquat : The organic cation formed formally by addition of an ethylene bridge between the nitrogen atoms of 2,2'-bipyridine. Most often available as the dibromide.	2.03	1	0	organic cation	defoliant; herbicide
benzo(f)quinoline [no description available]	1.96	1	0
n-nitrosodiphenylamine N-nitrosodiphenylamine: RN given refers to parent cpd; structure in first source	2.37	2	0	phenylhydrazines
1-hydroxy-2-naphthoic acid 1-hydroxy-2-naphthoic acid: RN given refers to parent cpd. 1-hydroxy-2-naphthoic acid : A naphthoic acid with the carboxy group at position 2 and carrying a hydroxy substituent at the 1-position. It is a xenobiotic metabolite produced by the biodegradation of phenanthrene by microorganisms.	2.07	1	0	hydroxy monocarboxylic acid; naphthoic acid; naphthols	bacterial xenobiotic metabolite; fungal xenobiotic metabolite
1-nitronaphthalene 1-nitronaphthalene: RN given refers to cpd with locant for nitro moiety in 1 position. 1-nitronaphthalene : A mononitronaphthalene substituted by a nitro group at position 1.. mononitronaphthalene : A nitronaphthalene carrying a single nitro group at unspecified position.. nitronaphthalene : A nitroarene that is naphthalene substituted by at least one nitro group.	2	1	0	mononitronaphthalene	environmental contaminant; mouse metabolite
fluorene [no description available]	4.28	18	0	ortho-fused polycyclic arene; ortho-fused tricyclic hydrocarbon
carbazole carbazole: structure in first source	2.7	3	0	carbazole
1,2,3-trichlorobenzene trichlorobenzene: commercial grade of trichlorobenzene containing 70% 1,2,4-trichlorobenzene & 30% 1,2,3-trichlorobenzene; see also record for 1,2,4-trichlorobenzene. trichlorobenzene : Any member of the class of chlorobenzenes carrying three chloro substituents at unspecified positions.. 1,2,3-trichlorobenzene : A trichlorobenzene carrying chloro substituents at positions 1, 2 and 3.	2.04	1	0	trichlorobenzene
hexamethylbenzene hexamethylbenzene : A methylbenzene that is benzene in which all six hydrogens have been replaced by methyl groups.	2.04	1	0	methylbenzene
2,4,6-trichlorophenol [no description available]	1.96	1	0	trichlorophenol	carcinogenic agent
n-vinyl-2-pyrrolidinone N-vinyl-2-pyrrolidinone: monomer of POVIDONE; structure given in first source	3.03	5	0	pyrrolidin-2-ones
2-tert-butyl-4-hydroxyanisole 2-tert-butyl-4-hydroxyanisole : An aromatic ether that is 4-methoxyphenol in which one of the hydrogens ortho- to the methoxy group is replaced by a tert-butyl group.	1.97	1	0	aromatic ether; phenols
2-anisidine 2-anisidine: RN given refers to parent cpd; structure. o-anisidine : A substituted aniline that is aniline in which the hydrogen ortho to the amino group has been replaced by a methoxy group. It is used as a chemical intermediate in the synthesis of azo pigments and dyes.	2.15	1	0	monomethoxybenzene; primary amino compound; substituted aniline	genotoxin; reagent
1-methylnaphthalene 1-methylnaphthalene : A methylnaphthalene carrying a methyl substituent at position 1.	2.43	2	0	methylnaphthalene	carcinogenic agent; plant metabolite
1-chloronaphthalene 1-chloronaphthalene: word preservative; in xylamon the active ingredient is 60% 1-chloronaphthalene; structure in Merck Index, 9th ed, #2126	2.04	1	0
1-naphthol 1-naphthol: RN given refers to parent cpd. 1-naphthol : A naphthol carrying a hydroxy group at position 1.. hydroxynaphthalene : Any member of the class of naphthalenes that is naphthalene carrying one or more hydroxy groups.	8.48	8	0	naphthol	genotoxin; human xenobiotic metabolite
2-aminodiphenyl aminobiphenyl : Any member of the class of biphenyls in which the biphenyl skeleton is substituted by at least one amino group.	1.96	1	0
aminacrine Aminacrine: A highly fluorescent anti-infective dye used clinically as a topical antiseptic and experimentally as a mutagen, due to its interaction with DNA. It is also used as an intracellular pH indicator.. 9-aminoacridine : An aminoacridine that is acridine in which the hydrogen at position 9 is replaced by an amino group. A fluorescent dyd and topical antiseptic agent, it is used (usually as the hydrochloride salt) in eye drops for the treatment of superficial eye infections.	3.49	8	0	aminoacridines; primary amino compound	acid-base indicator; antiinfective agent; antiseptic drug; fluorescent dye; MALDI matrix material; mutagen
michler's ketone [no description available]	2.03	1	0	benzophenones
quinoxalines quinoxaline : A naphthyridine in which the nitrogens are at positions 1 and 4.	7.77	17	2	mancude organic heterobicyclic parent; naphthyridine; ortho-fused heteroarene
quinoline [no description available]	1.99	1	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinolines
2-methylnaphthalene 2-methylnaphthalene: RN given refers to parent cpd. 2-methylnaphthalene : A methylnaphthalene carrying a methyl substituent at position 2.	2.42	2	0	methylnaphthalene
2-chloronaphthalene 2-chloronaphthalene: structure in first source	2.04	1	0
2-naphthylamine 2-Naphthylamine: A naphthalene derivative with carcinogenic action.. 2-naphthylamine : A naphthylamine carrying the amino group at position 2.	4.96	12	0	naphthylamine	carcinogenic agent
naphthacene tetracene : An acene that consists of four ortho-fused benzene rings in a rectilinear arrangement.	2.04	1	0	acene; tetracenes
diphenyl diphenyl: RN given refers to unlabeled cpd; structure	2.04	1	0	aromatic fungicide; benzenes; biphenyls	antifungal agrochemical; antimicrobial food preservative
proflavine Proflavine: Topical antiseptic used mainly in wound dressings.. 3,6-diaminoacridine : An aminoacridine that is acridine that is substituted by amino groups at positions 3 and 6. A slow-acting bacteriostat that is effective against many Gram-positive bacteria (but ineffective against spores), its salts were formerly used for treatment of burns and infected wounds.	1.96	1	0	aminoacridines	antibacterial agent; antiseptic drug; carcinogenic agent; chromophore; intercalator
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.	5.17	15	0	aminobiphenyl	carcinogenic agent
xanthenes Xanthenes: Compounds with three aromatic rings in linear arrangement with an OXYGEN in the center ring.	2.1	1	0	xanthene
benzidine benzidine: RN given refers to parent cpd. benzidine : A member of the class of biphenyls that is 1,1'-biphenyl in which the hydrogen at the para-position of each phenyl group has been replaced by an amino group.	6.55	14	4	biphenyls; substituted aniline	carcinogenic agent
4-nitrobiphenyl 4-nitrobiphenyl: structure given in first source	1.99	1	0	biphenyls
veratryl alcohol (3,4-dimethoxyphenyl)methanol : A member of the class of benzyl alcohols that is benzyl alcohol in which the hydrogens at positions 3 and 4 of the phenyl group are substituted by methoxy groups.	6.96	1	0	benzyl alcohols; dimethoxybenzene; primary alcohol	fungal metabolite
benzoylacetone [no description available]	1.97	1	0
propylparaben Parabens: Methyl, propyl, butyl, and ethyl esters of p-hydroxybenzoic acid. They have been approved by the FDA as antimicrobial agents for foods and pharmaceuticals. (From Hawley's Condensed Chemical Dictionary, 11th ed, p872)	3.21	5	0	benzoate ester; paraben; phenols	antifungal agent; antimicrobial agent
butylparaben [no description available]	2.58	2	0	organic molecular entity
dihydrosafrole [no description available]	1.97	1	0	benzodioxoles
2-methyl-4-chlorophenoxyacetic acid 2-Methyl-4-chlorophenoxyacetic Acid: A powerful herbicide used as a selective weed killer.. (4-chloro-2-methylphenoxy)acetic acid : A chlorophenoxyacetic acid that is (4-chlorophenoxy)acetic acid substituted by a methyl group at position 2.	1.99	1	0	chlorophenoxyacetic acid; monochlorobenzenes	environmental contaminant; phenoxy herbicide; synthetic auxin
2-xylene 2-xylene: RN given refers to parent cpd. o-xylene : A xylene substituted by methyl groups at positions 1 and 2.	2.04	1	0	xylene
2-chlorotoluene 2-chlorotoluene: RN given refers to parent cpd	2.04	1	0
2-dichlorobenzene 2-dichlorobenzene: structure. 1,2-dichlorobenzene : A dichlorobenzene carrying chloro substituents at positions 1 and 2.	2.45	2	0	dichlorobenzene	hepatotoxic agent; metabolite
2-toluidine 2-toluidine: RN given refers to parent cpd. o-toluidine : An aminotoluene in which the amino substituent is ortho to the methyl group.	1.98	1	0	aminotoluene	carcinogenic agent
pseudocumene 1,2,4-trimethylbenzene : A trimethylbenzene carrying methyl groups at positions 1, 2 and 4.	2.04	1	0	trimethylbenzene	neurotoxin
2,4-diaminotoluene 2,4-diaminotoluene: RN given refers to unlabeled parent cpd; structure. 2,4-diaminotoluene : An aminotoluene that is para-toluidine with an additional amino group at position 2.	2.05	1	0	aminotoluene	metabolite
durene durene: structure. durene : A tetramethylbenzene carrying methyl groups at positions 1, 2, 4 and 5.	2.04	1	0	tetramethylbenzene
1,2,4,5-tetrachlorobenzene 1,2,4,5-tetrachlorobenzene : A tetrachlorobenzene carrying chloro groups at positions 1, 2, 4 and 5.	2.04	1	0	tetrachlorobenzene
2,4,5-trichlorophenol 2,4,5-trichlorophenol: RN given refers to parent cpd; structure. 2,4,5-trichlorophenol : A trichlorophenol carrying chloro groups at positions 2, 4 and 5.	7	1	0	trichlorophenol
styrene oxide styrene oxide: structure. styrene oxide : An epoxide that is oxirane in which one of the hydrogens has been replaced by a phenyl group.	2.89	4	0	epoxide	human xenobiotic metabolite
methyl acrylate [no description available]	1.98	1	0	enoate ester
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.	2.1	1	0	butan-4-olide	metabolite; neurotoxin
2,4-di-tert-butylphenol 2,4-di-tert-butylphenol: structure given in first source. 2,4-di-tert-butylphenol : A member of the class of phenols carrying two tert-butyl substituents at positions 2 and 4.	2.03	1	0	alkylbenzene; phenols	antioxidant; bacterial metabolite; marine metabolite
o-aminoazotoluene o-Aminoazotoluene: An azo dye with carcinogenic properties.	2.41	2	0
ethylene dimethacrylate ethylene glycol dimethacrylate : The enoate ester that is the 1,2-bis(methacryloyl) derivative of ethylene glycol.	2.07	1	0	enoate ester	allergen; cross-linking reagent; polymerisation monomer
tert-butylbenzene [no description available]	2.04	1	0
pyrrolidonecarboxylic acid Pyrrolidonecarboxylic Acid: A cyclized derivative of L-GLUTAMIC ACID. Elevated blood levels may be associated with problems of GLUTAMINE or GLUTATHIONE metabolism.. 5-oxo-L-proline : An optically active form of 5-oxoproline having L-configuration.	2.59	2	0	5-oxoproline; L-proline derivative; non-proteinogenic L-alpha-amino acid	algal metabolite
cumene cumene : An alkylbenzene that is benzene carrying an isopropyl group.	2.04	1	0	alkylbenzene
nitrobenzene nitrobenzene : A nitroarene consisting of benzene carrying a single nitro substituent. An industrial chemical used widely in the production of aniline.	2	1	0	nitroarene; nitrobenzenes
trehalose alpha,alpha-trehalose : A trehalose in which both glucose residues have alpha-configuration at the anomeric carbon.	6.98	1	0	trehalose	Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
1,2-dichloro-4-nitrobenzene [no description available]	2.04	1	0
methylparaben methylparaben: used as a preservative in cosmetics but potentiates UV-induced damage of skin; RN given refers to parent cpd. methylparaben : A 4-hydroxybenzoate ester resulting from the formal condensation of the carboxy group of 4-hydroxybenzoic acid with methanol. It is the most frequently used antimicrobial preservative in cosmetics. It occurs naturally in several fruits, particularly in blueberries.	2.53	2	0	paraben	antifungal agent; antimicrobial food preservative; neuroprotective agent; plant metabolite
4-cymene 4-cymene: structure. p-cymene : A monoterpene that is toluene substituted by an isopropyl group at position 4.	2.04	1	0	monoterpene; toluenes	human urinary metabolite; plant metabolite; volatile oil component
4-nitroanisole 4-nitroanisole: dye intermediate; organic synthesis; structure. 4-nitroanisole : A member of the class of 4-nitroanisoles that is anisole in which one the hydrogen meta to the methoxy group is replaced by a nitro group.	2.88	4	0	4-nitroanisoles
4-nitrophenetol [no description available]	1.96	1	0
benzyl bromide benzyl bromide: structure given in first source. benzyl bromide : A member of the class of benzyl bromides that is toluene substituted on the alpha-carbon with bromine.	2.31	1	0	benzyl bromides	lachrymator
4-vinylcyclohexene 4-vinylcyclohexene: structure	2	1	0	cyclic olefin
ethylbenzene [no description available]	2.04	1	0	alkylbenzene
styrene Styrene: A colorless, toxic liquid with a strong aromatic odor. It is used to make rubbers, polymers and copolymers, and polystyrene plastics.. styrene : A vinylarene that is benzene carrying a vinyl group. It has been isolated from the benzoin resin produced by Styrax species.	2.4	2	0	styrenes; vinylarene; volatile organic compound	mouse metabolite; mutagen; plant metabolite
phenylhydrazine [no description available]	2.1	1	0	phenylhydrazines	xenobiotic
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.	2.67	3	0	nitrosamine; piperidine	apoptosis inducer; carcinogenic agent; environmental contaminant; mutagen
methylenebis(chloroaniline) Methylenebis(chloroaniline): Aromatic diamine used in the plastics industry as curing agent for epoxy resins and urethane rubbers. It causes bladder, liver, lung, and other neoplasms.. 4,4'-methylene-bis-(2-chloroaniline) : A chloroaniline that consists of two 2-chloroaniline units joined by a methylene bridge.	2.39	2	0	chloroaniline	metabolite
2-ethylhexyl acrylate [no description available]	1.98	1	0	enoate ester
1,2-dihydrostilbene 1,2-dihydrostilbene: intermdiate in biosynthesis of dihydrophenanthrenes from phenylalanine. 1,2-dihydrostilbene : A diphenylethane that is the 1,2-dihydro derivative of stilbene.	2.04	1	0	diphenylethane
n-propylbenzene n-propylbenzene: RN given refers to parent cpd. propylbenzene : An alkylbenzene that is benzene having one of its aromatic hydrogens substituted by a propyl group.	2.04	1	0	alkylbenzene
n-butylbenzene butylbenzene : An alkylbenzene that is benzene substituted by a butyl group at position 1.	2.04	1	0	alkylbenzene
ethyl bromoacetate [no description available]	4.9	1	1
methyl acetoacetate methyl acetoacetate: structure	2.11	1	0	oxo carboxylic acid
caprolactam Caprolactam: Cyclic amide of caproic acid used in manufacture of synthetic fibers of the polyamide type. Can cause local irritation.. epsilon-caprolactam : A member of the class of caprolactams that is azepane substituted by an oxo group at position 2.	1.97	1	0	caprolactams	human blood serum metabolite
ethyl laurate ethyl laurate : A fatty acid ethyl ester of lauric acid.	1.97	1	0	fatty acid ethyl ester	metabolite
1,4-dibromobenzene [no description available]	2.04	1	0	dibromobenzene
4-xylene p-xylene : A xylene with methyl groups at positions 1 and 4.	2.89	4	0	xylene
4-chlorotoluene 4-chlorotoluene: RN given refers to unlabeled cpd	2.42	2	0	monochlorobenzenes
4-vinyl-1-cyclohexene dioxide 4-vinyl-1-cyclohexene dioxide: activates caspase cascades; structure. 4-vinylcyclohexene dioxide : The diepoxide of 4-vinylcyclohexene.	2	1	0	epoxide	carcinogenic agent
epichlorohydrin Epichlorohydrin: A chlorinated epoxy compound used as an industrial solvent. It is a strong skin irritant and carcinogen.. epichlorohydrin : An epoxide that is 1,2-epoxypropene in which one of the methyl hydrogens is substituted by chlorine.	1.97	1	0	epoxide; organochlorine compound
ethylene dibromide Ethylene Dibromide: An effective soil fumigant, insecticide, and nematocide. In humans, it causes severe burning of skin and irritation of the eyes and respiratory tract. Prolonged inhalation may cause liver necrosis. It is also used in gasoline. Members of this group have caused liver and lung cancers in rodents. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), 1,2-dibromoethane may reasonably be anticipated to be a carcinogen.. 1,2-dibromoethane : A bromoalkane that is ethane carrying bromo substituents at positions 1 and 2. It is produced by marine algae.	2.4	2	0	bromoalkane; bromohydrocarbon	algal metabolite; carcinogenic agent; fumigant; marine metabolite; mouse metabolite; mutagen
butane butane : A straight chain alkane composed of 4 carbon atoms.	2.04	1	0	alkane; gas molecular entity	food propellant; refrigerant
1-butene but-1-ene : A butene with unsaturation at position 1.	2.48	2	0	butene
1,3-butadiene buta-1,3-diene : A butadiene with unsaturation at positions 1 and 3.	3.8	3	0	butadiene	carcinogenic agent; mutagen
acrolein [no description available]	2.94	4	0	enal	herbicide; human xenobiotic metabolite; toxin
allylamine Allylamine: Possesses an unusual and selective cytotoxicity for VASCULAR SMOOTH MUSCLE cells in dogs and rats. Useful for experiments dealing with arterial injury, myocardial fibrosis or cardiac decompensation.	4	2	0	alkylamine
acrylonitrile [no description available]	2.38	2	0	aliphatic nitrile; volatile organic compound	antifungal agent; carcinogenic agent; fungal metabolite; mutagen; polar aprotic solvent
2-methylpentane Hexanes: Six-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Various polyneuropathies are caused by hexane poisoning.	2.93	4	0	alkane
methyl isobutyl ketone [no description available]	2.02	1	0	ketone
acetic anhydride acetic anhydride: RN given refers to unlabeled cpd; structure. acetic anhydride : An acyclic carboxylic anhydride derived from acetic acid.	2	1	0	acyclic carboxylic anhydride	metabolite; reagent
3-xylene m-xylene : A xylene carrying methyl groups at positions 1 and 3.	2.4	2	0	xylene
mesitylene mesitylene: structure. 1,3,5-trimethylbenzene : A trimethylbenzene carrying methyl substituents at positions 1, 3 and 5.	2.04	1	0	trimethylbenzene
1,3,5-trichlorobenzene 1,3,5-trichlorobenzene: structure in first source. 1,3,5-trichlorobenzene : A trichlorobenzene carrying chloro substituents at positions 1, 3 and 5.	2.04	1	0	trichlorobenzene
bromobenzene [no description available]	2.87	4	0	bromoarene; bromobenzenes; volatile organic compound	hepatotoxic agent; mouse metabolite; non-polar solvent
chlorobenzene [no description available]	2.69	3	0	monochlorobenzenes	solvent
pentane Pentanes: Five-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives.. pentane : A straight chain alkane consisting of 5 carbon atoms.	2.41	2	0	alkane; volatile organic compound	non-polar solvent; refrigerant
1-pentene 1-pentene: structure in first source	2.04	1	0
butyl chloride butyl chloride: structure	2.04	1	0
pyrroles 1H-pyrrole : A tautomer of pyrrole that has the double bonds at positions 2 and 4.. pyrrole : A five-membered monocyclic heteroarene comprising one NH and four CH units which forms the parent compound of the pyrrole group of compounds. Its five-membered ring structure has three tautomers. A 'closed class'.. azole : Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen.	2.36	2	0	pyrrole; secondary amine
tetrahydrofuran oxolane : A cyclic ether that is butane in which one hydrogen from each methyl group is substituted by an oxygen.	2.89	4	0	cyclic ether; oxolanes; saturated organic heteromonocyclic parent; volatile organic compound	polar aprotic solvent
thiophenes Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.	4.14	16	0	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
n-hexane hexane : An unbranched alkane containing six carbon atoms.	2.7	3	0	alkane; volatile organic compound	neurotoxin; non-polar solvent
cyclohexane Cyclohexane: C6H12. cyclohexane : An alicyclic hydrocarbon comprising a ring of six carbon atoms; the cyclic form of hexane, used as a raw material in the manufacture of nylon.	2.04	1	0	cycloalkane; volatile organic compound	non-polar solvent
cyclohexene cyclohexene : A cycloalkene that is cylohexane with a single double bond.	2.04	1	0	cycloalkene
dipropyl sulfide [no description available]	2.91	4	0	aliphatic sulfide
heptanal heptanal : An n-alkanal resulting from the oxidation of the alcoholic hydroxy group of heptan-1-ol to the corresponding aldehyde. An endogenous aldehyde coming from membrane lipid oxidation, it is found in the blood of lung cancer patients and has been regarded as a potential biomarker of lung cancer.	2.06	1	0	medium-chain fatty aldehyde; n-alkanal; saturated fatty aldehyde	biomarker
nonane iotrochotin: toxin from the Caribbean sponge Iotrochota birotulata, which selectively permeabilizes synaptosomes. nonane : A straight chain alkane composed of 9 carbon atoms.	2.04	1	0	alkane	plant metabolite; volatile oil component
octylamine octylamine: RN given refers to 1-octylamine. octan-1-amine : An 8-carbon primary aliphatic amine.	1.96	1	0	primary aliphatic amine	metabolite
triethylene glycol triethylene glycol : A poly(ethylene glycol) that is octane-1,8-diol in which the carbon atoms at positions 3 and 6 have been replaced by oxygen atoms.	2.38	2	0	diol; poly(ethylene glycol); primary alcohol	plasticiser
n-dodecane dodecane : A straight-chain alkane with 12 carbon atoms. It has been isolated from the essential oils of various plants including Zingiber officinale (ginger).	2.67	3	0	alkane	plant metabolite
2,2,2-trichloroethanol [no description available]	1.96	1	0	chloroethanol	mouse metabolite
diethylhexyl phthalate Diethylhexyl Phthalate: An ester of phthalic acid. It appears as a light-colored, odorless liquid and is used as a plasticizer for many resins and elastomers.. bis(2-ethylhexyl) phthalate : A phthalate ester that is the bis(2-ethylhexyl) ester of benzene-1,2-dicarboxylic acid.	3.89	12	0	diester; phthalate ester	androstane receptor agonist; apoptosis inhibitor; plasticiser
hexachlorobenzene Hexachlorobenzene: An agricultural fungicide and seed treatment agent.. hexachlorobenzene : A member of the class of chlorobenzenes that is benzene in which all of the hydrogens are replaced by chlorines. An agricultural fungicide introduced in the mid-1940s and formerly used as a seed treatment, its use has been banned since 1984 under the Stockholm Convention on Persistent Organic Pollutants.	9.02	14	0	aromatic fungicide; chlorobenzenes	antifungal agrochemical; carcinogenic agent; persistent organic pollutant
trinitrotoluene Trinitrotoluene: A 2,4,6-trinitrotoluene, which is an explosive chemical that can cause skin irritation and other toxic consequences.. 2,4,6-trinitrotoluene : A trinitrotoluene having the nitro groups at positions 2, 4 and 6.	2.7	3	0	trinitrotoluene	explosive
framycetin Framycetin: A component of NEOMYCIN that is produced by Streptomyces fradiae. On hydrolysis it yields neamine and neobiosamine B. (From Merck Index, 11th ed). framycetin : A tetracyclic antibacterial agent derived from neomycin, being a glycoside ester of neamine and neobiosamine B.	1.93	1	0	aminoglycoside	allergen; antibacterial drug; Escherichia coli metabolite
benzoin [no description available]	1.98	1	0	benzoins; secondary alpha-hydroxy ketone	EC 3.1.1.1 (carboxylesterase) inhibitor
anthracene acene : A polycyclic aromatic hydrocarbon consisting of fused benzene rings in a rectilinear arrangement.. acenes : Polycyclic aromatic hydrocarbons consisting of fused benzene rings in a rectilinear arrangement and their substitution derivatives.	7.84	56	0	acene; anthracenes; ortho-fused tricyclic hydrocarbon
dibenzoylmethane dibenzoylmethane : A beta-diketone that is acetylacetone (acac) in which both methyl groups have been replaced by phenyl groups. It is a minor constituent of the root extract of licorice (Glycyrrhiza glabra) and exhibits antimutagenic and anticancer effects.	7.92	4	0	aromatic ketone; beta-diketone	antimutagen; antineoplastic agent; metabolite
piperonal piperonal: has been used as a pediculicide; structure. piperonal : An arenecarbaldehyde that is 1,3-benzodioxole substituted by a formyl substituent at position 5. It has been isolated from Piper nigrum.	6.93	1	0	arenecarbaldehyde; benzodioxoles	fragrance; insect repellent; plant metabolite
vanillic acid Vanillic Acid: A flavoring agent. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13).. vanillic acid : A monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3.	7.69	2	0	methoxybenzoic acid; monohydroxybenzoic acid	plant metabolite
triethylamine [no description available]	2.31	1	0	tertiary amine
cyclonite cyclonite: explosive & convulsant; structure. 1,3,5-trinitro-1,3,5-triazinane : An N-nitro compound that is 1,3,5-triazinane in which all three of the hydrogens attached to the nitrogens have been replaced by nitro groups. It is widely used in both industrial and military explosives.	3.16	1	0	1,3,5-triazinanes; N-nitro compound	explosive
pyrazolanthrone pyrazolanthrone: JNK (c-Jun N-terminal kinase) inhibitor; structure in first source. anthra[1,9-cd]pyrazol-6(2H)-one : A member of the class of anthrapyrazoles that is anthra[1,9-cd]pyrazole substituted at position 6 by an oxo group. An inhibitor of c-Jun N-terminal kinase.	2.25	1	0	anthrapyrazole; aromatic ketone; cyclic ketone	antineoplastic agent; c-Jun N-terminal kinase inhibitor; geroprotector
2,4,7-trinitrofluorenone 2,4,7-trinitrofluorenone: structure	2.4	2	0
1,4-naphthoquinone naphthoquinone : A polycyclic aromatic ketone metabolite of naphthalene.. 1,4-naphthoquinone : The parent structure of the family of 1,4-naphthoquinones, in which the oxo groups of the quinone moiety are at positions 1 and 4 of the naphthalene ring. Derivatives have pharmacological properties.	2.42	2	0	1,4-naphthoquinones
1-naphthylamine 1-Naphthylamine: A suspected industrial carcinogen (and listed as such by OSHA). Its N-hydroxy metabolite is strongly carcinogenic and mutagenic.. naphthylamine : A primary arylamine that is naphthalene substituted by an amino group at unspecified position.. 1-naphthylamine : A naphthylamine that is naphthalene substituted by an amino group at position 1.	1.97	1	0	naphthylamine	human xenobiotic metabolite
2-naphthol 2-naphthol: RN given refers to parent cpd. 2-naphthol : A naphthol carrying a hydroxy group at position 2.. naphthols : Any hydroxynaphthalene derivative that has a single hydroxy substituent.	6.26	11	1	naphthol	antinematodal drug; genotoxin; human urinary metabolite; human xenobiotic metabolite; mouse metabolite; radical scavenger
neozone N-phenyl-2-naphthalenamine: structure in first source	3.09	1	0	naphthalenes
4-tert-octylphenol 4-tert-octylphenol: structure given in first source	2.03	1	0	alkylbenzene
citronellol citronellol: alcohol form of citronellal; found in rose oil; RN given refers to parent cpd without isomeric designation; structure. citronellol : A monoterpenoid that is oct-6-ene substituted by a hydroxy group at position 1 and methyl groups at positions 3 and 7.. insect repellent : An insecticide that acts as a repellent to insects.	4.9	1	1	monoterpenoid	plant metabolite
ethyl acetate ethyl acetate : The acetate ester formed between acetic acid and ethanol.	3.08	5	0	acetate ester; ethyl ester; volatile organic compound	EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor; metabolite; polar aprotic solvent; Saccharomyces cerevisiae metabolite
n-heptane Heptanes: Seven-carbon alkanes with the formula C7H16.. heptane : A straight-chain alkane with seven carbon atoms. It has been found in Jeffrey pine (Pinus jeffreyi).	2.04	1	0	alkane; volatile organic compound	non-polar solvent; plant metabolite
pregnenolone [no description available]	2.37	2	0	20-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; C21-steroid	human metabolite; mouse metabolite
acridine mustard acridine mustard: ICR 170 was heading 1975-95 (see under NITROGEN MUSTARD COMPOUNDS 1975-90); ACRIDINE MUSTARD was see ICR 170 1981-95; use ICR-170 (NM) to search ICR 170 1975-95	1.98	1	0	acridines	intercalator
2-vanillin ortho-vanillin : A member of the class of benzaldehydes that is salicylaldehyde substituted by a methoxy group at position 3.	2	1	0	benzaldehydes; guaiacols	antimutagen; plant metabolite
1,2-dihydroxybenzene-3,5-disulfonic acid disodium salt 1,2-Dihydroxybenzene-3,5-Disulfonic Acid Disodium Salt: A colorimetric reagent for iron, manganese, titanium, molybdenum, and complexes of zirconium. (From Merck Index, 11th ed)	1.97	1	0	organic molecular entity
mequinol mequinol: depigmenting agent; RN given refers to parent cpd	1.96	1	0	methoxybenzenes; phenols	metabolite
potassium cyanide [no description available]	5.19	3	1	cyanide salt; one-carbon compound; potassium salt	EC 1.15.1.1 (superoxide dismutase) inhibitor; EC 1.9.3.1 (cytochrome c oxidase) inhibitor; neurotoxin
cycloguanil cycloguanil: the active metabolite of proguanil; antifolate drug; structure in first source. cycloguanil : A triazine in which a 1,6-dihydro-1,3,5-triazine ring is substituted at N-1 by a 4-chlorophenyl group, at C-2 and -4 by amino groups and at C-6 by gem-dimethyl groups. A dihydrofolate reductase inhibitor, it is a metabolite of the antimalarial drug proguanil.	2.11	1	0	triazines	antifolate; antiinfective agent; antimalarial; antiparasitic agent; antiprotozoal drug; EC 1.5.1.3 (dihydrofolate reductase) inhibitor
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.	11.03	35	0	catechin	antioxidant; plant metabolite
dibenzo(a,i)pyrene [no description available]	2.44	2	0	ortho- and peri-fused polycyclic arene
dibenzo(a,h)pyrene dibenzo(a,h)pyrene: structure given in first source	2.06	1	0	ortho- and peri-fused polycyclic arene
coronene coronene: structure. coronene : A ortho- and peri-fused polycyclic arene that consists of six peri-fused benzene rings.	7.41	2	0	ortho- and peri-fused polycyclic arene
1,12-benzoperylene 1,12-benzoperylene: structure; see also record for benzoperylene	3.29	6	0	ortho- and peri-fused polycyclic arene
dibenzo(a,l)pyrene dibenzo(a,l)pyrene: structure in first source	4.67	27	0	ortho- and peri-fused polycyclic arene	human metabolite; mutagen
benzo(e)pyrene benzo(e)pyrene: RN given refers to parent cpd. benzo[e]pyrene : An ortho- and peri-fused polycyclic arene consisting of five fused benzene rings. It is listed as a Group 3 carcinogen by the IARC.	6.05	38	0	ortho- and peri-fused polycyclic arene	carcinogenic agent; mutagen
indeno(1,2,3-cd)pyrene indeno(1,2,3-cd)pyrene: structure in first source	3.66	9	0	pyrenes
7h-dibenzo(c,g)carbazole [no description available]	9.18	17	0	carbazoles
benzo(c)phenanthrene benzo[c]phenanthrene : An ortho-fused polycyclic arene resulting from the symmetrical fusion of the C1-C2 bonds of two naphthalene units.	4.48	7	0	benzenoid aromatic compound; ortho-fused polycyclic arene
perylene Perylene: A 20-carbon dibenz(de,kl)anthracene that can be viewed as a naphthalene fused to a phenalene or as dinaphthalene. It is used as fluorescent lipid probe in the cytochemistry of membranes and is a polycyclic hydrocarbon pollutant in soil and water. Derivatives may be carcinogenic.. perylene : An ortho- and peri-fused polycyclic arene comprising of five benzene rings that is anthracene in which the d,e and k,l sides are fused to benzene rings.	5.59	23	0	ortho- and peri-fused polycyclic arene; perylenes
benzo(c)fluorene benzo(c)fluorene: structure in first source	2.13	1	0	carbotetracyclic compound
benzo(j)fluoranthene benzo(j)fluoranthene: dihydrodiol metabolites identified as mutagens; structure given in first source	2.71	3	0	naphthalenes
benzo(b)fluoranthene benzo[b]fluoranthene : An ortho- and peri-fused polycyclic arene that consists of a benzene ring fused with a acephenanthrylene ring.	6.54	34	0	ortho- and peri-fused polycyclic arene	mutagen
fluoranthene fluoranthene: structure. fluoranthene : An ortho- and peri-fused polycyclic arene consisting of a naphthalene and benzene unit connected by a five-membered ring.	5.61	70	0	ortho- and peri-fused polycyclic arene
benzo(k)fluoranthene [no description available]	5.88	30	0	naphthalenes
acenaphthylene acenaphthylene: RN given refers to parent cpd. acenaphthylene : A ortho- and peri-fused tricyclic hydrocarbon that occurs in coal tar.	3.55	2	0	acenaphthylenes; ortho- and peri-fused polycyclic arene; ortho- and peri-fused tricyclic hydrocarbon
picene picene: structure given in first source. picene : An ortho-fused polycyclic arene consisting of five fused benzene rings. It is obtained during the distillation of petroleum.	1.97	1	0	ortho-fused polycyclic arene
benzotriphenylene [no description available]	2.9	4	0	carbopolycyclic compound
dibenzacridine dibenzacridine: RN given refers to dibenz(a,j)acridine	3.68	10	0
triphenylene triphenylene: structure. triphenylene : An ortho-fused polycyclic arene consisting of four fused benzene rings.	2.04	1	0	ortho-fused polycyclic arene
chrysene chrysene: structure in Merck Index, 9th ed, #2252. chrysene : An ortho-fused polycyclic arene found commonly in the coal tar.	7.59	67	0	ortho-fused polycyclic arene	plant metabolite
dibenzo(aj)anthracene dibenzo(aj)anthracene: structure in first source	2.04	1	0	phenanthrenes
benz(a)acridine [no description available]	2.37	2	0	organonitrogen heterocyclic compound; polycyclic heteroarene
benz(c)acridine [no description available]	1.96	1	0	organonitrogen heterocyclic compound; polycyclic heteroarene
benzo(a)fluorene benzo(a)fluorene: structure in first source	2.47	2	0	carbotetracyclic compound
benzo(b)fluorene benzo(b)fluorene: structure in first source	2.04	1	0	carbotetracyclic compound
quinazolines Quinazolines: A group of aromatic heterocyclic compounds that contain a bicyclic structure with two fused six-membered aromatic rings, a benzene ring and a pyrimidine ring.. quinazoline : A mancude organic heterobicyclic parent that is naphthalene in which the carbon atoms at positions 1 and 3 have been replaced by nitrogen atoms.. quinazolines : Any organic heterobicyclic compound based on a quinazoline skeleton and its substituted derivatives.	2.73	3	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinazolines
acridines Acridines: Compounds that include the structure of acridine.. acridine : A polycyclic heteroarene that is anthracene in which one of the central CH groups is replaced by a nitrogen atom.	5.15	15	0	acridines; mancude organic heterotricyclic parent; polycyclic heteroarene	genotoxin
dibenzo(1,4)dioxin dibenzo(1,4)dioxin: structure	2	1	0	dibenzodioxine; heteranthrene; mancude organic heterotricyclic parent; oxacycle; polycyclic heteroarene
benzofuran benzofuran: RN & structure given in first source. 1-benzofuran : A benzofuran consisting of fused benzene and furan rings. It is the parent compound of the class of 1-benzofurans.	2.21	1	0	1-benzofurans; benzofuran
adamantane Adamantane: A tricyclo bridged hydrocarbon.	2.04	1	0	adamantanes; polycyclic alkane
cyclopentane Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.	5.41	4	1	cycloalkane; cyclopentanes; volatile organic compound	non-polar solvent
isoxazoles Isoxazoles: Azoles with an OXYGEN and a NITROGEN next to each other at the 1,2 positions, in contrast to OXAZOLES that have nitrogens at the 1,3 positions.. isoxazole : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing three carbon atoms and an oxygen and nitrogen atom adjacent to each other. It is the parent of the class of isoxazoles.. isoxazoles : Oxazoles in which the N and O atoms are adjacent.	4.9	1	1	isoxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
oxazoles Oxazoles: Five-membered heterocyclic ring structures containing an oxygen in the 1-position and a nitrogen in the 3-position, in distinction from ISOXAZOLES where they are at the 1,2 positions.. 1,3-oxazole : A five-membered monocyclic heteroarene that is an analogue of cyclopentadiene with O in place of CH2 at position 1 and N in place of CH at position 3.. oxazole : An azole based on a five-membered heterocyclic aromatic skeleton containing one N and one O atom.	2.45	2	0	1,3-oxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
thiazoles [no description available]	3.97	13	0	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
pyrazines Pyrazines: A heterocyclic aromatic organic compound with the chemical formula C4H4N2.. pyrazine : A diazine that is benzene in which the carbon atoms at positions 1 and 4 have been replaced by nitrogen atoms.	3.51	8	0	diazine; pyrazines	Daphnia magna metabolite
cyclooctane [no description available]	2.04	1	0
allylisopropylacetamide Allylisopropylacetamide: An allylic compound that acts as a suicide inactivator of CYTOCHROME P450 by covalently binding to its heme moiety or surrounding protein.	7.65	3	0
hydrazine diamine : Any polyamine that contains two amino groups.	2.67	3	0	azane; hydrazines	EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
paraoxon [no description available]	1.96	1	0	aryl dialkyl phosphate; organophosphate insecticide	EC 3.1.1.7 (acetylcholinesterase) inhibitor; mouse metabolite
aminophylline Aminophylline: A drug combination that contains THEOPHYLLINE and ethylenediamine. It is more soluble in water than theophylline but has similar pharmacologic actions. It's most common use is in bronchial asthma, but it has been investigated for several other applications.. aminophylline : A mixture comprising of theophylline and ethylenediamine in a 2:1 ratio.	1.97	1	0	mixture	bronchodilator agent; cardiotonic drug
azacitidine Azacitidine: A pyrimidine analogue that inhibits DNA methyltransferase, impairing DNA methylation. It is also an antimetabolite of cytidine, incorporated primarily into RNA. Azacytidine has been used as an antineoplastic agent.. 5-azacytidine : An N-glycosyl-1,3,5-triazine that is 4-amino-1,3,5-triazin-2(1H)-one substituted by a beta-D-ribofuranosyl residue via an N-glycosidic linkage. An antineoplastic agent, it is used in the treatment of myeloid leukaemia.	3.24	6	0	N-glycosyl-1,3,5-triazine; nucleoside analogue	antineoplastic agent
perfluorooctanoic acid perfluorooctanoic acid: RN given refers to parent cpd. perfluorooctanoic acid : A fluoroalkanoic acid that is perfluorinated octanoic acid.	2.77	3	0	fluoroalkanoic acid	carcinogenic agent; endocrine disruptor; environmental contaminant; surfactant; xenobiotic
diethyl sulfide ethyl sulfide : An aliphatic sulfide in which the sulfur atom is bonded to at least one ethyl group.. diethyl sulfide : An ethyl sulfide compound having two ethyl groups attached to a sulfur atom.	2.04	1	0	ethyl sulfide
thymidine monophosphate Thymidine Monophosphate: 5-Thymidylic acid. A thymine nucleotide containing one phosphate group esterified to the deoxyribose moiety.. dTMP : The neutral species of thymidine 5'-monophosphate (2'-deoxythymidine 5'-monophosphate).	2.38	2	0	thymidine 5'-monophosphate	fundamental metabolite
citrulline citrulline : The parent compound of the citrulline class consisting of ornithine having a carbamoyl group at the N(5)-position.	2.21	1	0	amino acid zwitterion; citrulline	Daphnia magna metabolite; EC 1.14.13.39 (nitric oxide synthase) inhibitor; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; protective agent; Saccharomyces cerevisiae metabolite
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
2-aminopurine 2-Aminopurine: A purine that is an isomer of ADENINE (6-aminopurine).. aminopurine : Any purine having at least one amino substituent.. 2-aminopurine : The parent compound of the 2-aminopurines, comprising a purine core carrying an amino substituent at the 2-position.	2.03	1	0	2-aminopurines; nucleobase analogue	antimetabolite
fluorobenzenes Fluorobenzenes: Derivatives of BENZENE that contain FLUORINE.. monofluorobenzene : The simplest member of the class of monofluorobenzenes that is benzene carrying a single fluoro substituent.. fluorobenzenes : Any fluoroarene that is a benzene or a substituted benzene carrying at least one fluoro group.	2.04	1	0	monofluorobenzenes	NMR chemical shift reference compound
naphthazarin naphthazarin: fish toxin; isolated for first time from the walnut onigurmi, Juglans mandshurica maxim var. Sieboldiana Makino; structure. naphthazarin : A naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 5 and 8 are replaced by hydroxy groups.	6.97	1	0	hydroxy-1,4-naphthoquinone	acaricide; antibacterial agent; antineoplastic agent; apoptosis inducer; geroprotector; plant metabolite
fusarium Fusarium: A mitosporic Hypocreales fungal genus, various species of which are important parasitic pathogens of plants and a variety of vertebrates. Teleomorphs include GIBBERELLA.	8.31	6	0
cholanthrene cholanthrene: structure given in first source	2.4	2	0
menadiol [no description available]	2.04	1	0	methylnaphthalenes; naphthalenediols; naphthohydroquinone
imperatorin imperatorin: tumor necrosis factor antagonist; furanocoumarin from West African medicinal plant Clausena anisata; structure in Negwer, 5th ed, #3005. imperatorin : A member of the class of psoralens that is psoralen substituted by a prenyloxy group at position 8. Isolated from Angelica dahurica and Angelica koreana, it acts as a acetylcholinesterase inhibitor.	2.69	3	0	psoralens	EC 3.1.1.7 (acetylcholinesterase) inhibitor; metabolite
indigo [no description available]	2.05	1	0	hydroxyindoles
retene retene: structure in first source	2.15	1	0
dihydralazine Dihydralazine: 1,4-Dihydrazinophthalazine. An antihypertensive agent with actions and uses similar to those of HYDRALAZINE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p354)	1.98	1	0	phthalazines
9-fluorenone fluoren-9-one : The simplest member of the class fluoren-9-ones that is 9H-fluorene bearing an oxo substituent at position 9.	1.97	1	0	fluoren-9-ones	fungal xenobiotic metabolite
flavanone flavanone: RN given refers to cpd with unspecified isomeric designation; structure in first source. flavanone : The simplest member of the class of flavanones that consists of flavan bearing an oxo substituent at position 4.	1.98	1	0	flavanones
thymoquinone thymoquinone: constituent of cedarwood; can cause dermatitis; structure. thymoquinone : A member of the class of 1,4-benzoquinones that is 1,4-bezoquinone in which the hydrogens at positions 2 and 5 are replaced by methyl and isopropyl groups, respectively. It is a natural compound isolated from Nigella sativa which has demonstrated promising chemotherapeutic activity.	3.34	6	0	1,4-benzoquinones	adjuvant; anti-inflammatory agent; antidepressant; antineoplastic agent; antioxidant; cardioprotective agent; plant metabolite
carvacrol carvacrol : A phenol that is a natural monoterpene derivative of cymene. An inhibitor of bacterial growth, it is used as a food additive. Potent activator of the human ion channels transient receptor potential V3 (TRPV3) and A1 (TRPA1).	7.48	2	0	botanical anti-fungal agent; p-menthane monoterpenoid; phenols	agrochemical; antimicrobial agent; flavouring agent; TRPA1 channel agonist; volatile oil component
orcinol orcinol: used as reagent for pentoses, lignin, beet sugar, saccharoses, arabinose & diastase; RN given refers to parent cpd; structure. orcinol : A 5-alkylresorcinol in which the alkyl group is specified as methyl.	2.37	2	0	5-alkylresorcinol; dihydroxytoluene	Aspergillus metabolite
phorone phorone: an industrial solvent; structure	1.96	1	0	dialkenyl ketone
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.	5.31	3	1
oleanolic acid [no description available]	1.98	1	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	plant metabolite
abietic acid abietic acid : An abietane diterpenoid that is abieta-7,13-diene substituted by a carboxy group at position 18.	1.99	1	0	abietane diterpenoid; monocarboxylic acid	plant metabolite
podophyllotoxin Podophyllum: A genus of poisonous American herbs, family BERBERIDACEAE. The roots yield PODOPHYLLOTOXIN and other pharmacologically important agents. The plant was formerly used as a cholagogue and cathartic. It is different from the European mandrake, MANDRAGORA.	2.11	1	0	furonaphthodioxole; lignan; organic heterotetracyclic compound	antimitotic; antineoplastic agent; keratolytic drug; microtubule-destabilising agent; plant metabolite; tubulin modulator
hesperidin Hesperidin: A flavanone glycoside found in CITRUS fruit peels.. hesperidin : A disaccharide derivative that consists of hesperetin substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	7.96	10	1	3'-hydroxyflavanones; 4'-methoxyflavanones; dihydroxyflavanone; disaccharide derivative; flavanone glycoside; monomethoxyflavanone; rutinoside	mutagen
luminol Luminol: 5-Amino-2,3-dihydro-1,4-phthalazinedione. Substance that emits light on oxidation. It is used in chemical determinations.	3.47	2	0
1,2-naphthoquinone naphthalene-1,2-dione: structure given in first source. 1,2-naphthoquinone : The parent structure of the family of 1,2-naphthoquinones, in which the oxo groups of the quinone moiety are at positions 1 and 2 of the naphthalene ring. It is a metabolite of naphthalene and is found in diesel exhaust particles.	2.15	1	0	1,2-naphthoquinones	aryl hydrocarbon receptor agonist; carcinogenic agent
2,7-fluorenediamine 2,7-fluorenediamine: peroxidase reagent for blood smears; RN given refers to parent cpd	1.98	1	0
flavone flavone: RN given refers to unlabeled cpd; structure given in first source. flavone : The simplest member of the class of flavones that consists of 4H-chromen-4-one bearing a phenyl substituent at position 2.	7.71	3	0	flavones	metabolite; nematicide
hemimellitene hemimellitene: structure. 1,2,3-trimethylbenzene : A trimethylbenzene carrying methyl groups at positions 1, 2 and 3. It has been found in Centaurium erythraea.	2.04	1	0	trimethylbenzene	neurotoxin; plant metabolite
syringic acid syringic acid: RN given refers to parent cpd; structure in third source. syringic acid : A dimethoxybenzene that is 3,5-dimethyl ether derivative of gallic acid.	2.25	1	0	benzoic acids; dimethoxybenzene; phenols	plant metabolite
chrysoidine chrysoidine: RN given refers to parent cpd; structure	2.06	1	0
phenylacetylene phenylacetylene: can polymerize into DENDRIMERS	2.05	1	0	benzenes
tricaprylin tricaprylin: 13C-labeled trioctanoin used in breath tests to detect fat malabsorption. trioctanoin : A triglyceride obtained by acylation of the three hydroxy groups of glycerol by octanoic acid. Used as an alternative energy source to glucose for patients with mild to moderate Alzheimer's disease.	2.37	2	0	octanoate ester; triglyceride	anticonvulsant; plant metabolite
ethylene bromohydrin ethylene bromohydrin: RN given refers to 2-bromo cpd	1.96	1	0
1-chloropropane 1-chloropropane: structure in first source	2.04	1	0
2,2,4-trimethylpentane 2,2,4-trimethylpentane: nephrotoxic. isooctane : An alkane that consists of pentane bearing two methyl substituents at position 2 and a single methyl substituent at position 4.	2.04	1	0	alkane; volatile organic compound	fuel additive; nephrotoxin; non-polar solvent
1,3-dichlorobenzene 1,3-dichlorobenzene : A dichlorobenzene carrying chloro substituents at positions 1 and 3.	2.04	1	0	dichlorobenzene
malondialdehyde Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.	5.39	56	0	dialdehyde	biomarker
1-chlorohexane [no description available]	2.04	1	0
n-hexadecane n-hexadecane: structure. hexadecane : A straight-chain alkane with 16 carbon atoms. It is a component of essential oil isolated from long pepper.	2.91	4	0	long-chain alkane	non-polar solvent; plant metabolite; volatile oil component
gentian violet Gentian Violet: A dye that is a mixture of violet rosanilinis with antibacterial, antifungal, and anthelmintic properties.. crystal violet : An organic chloride salt that is the monochloride salt of crystal violet cation. It has been used in creams for the topical treatment of bacterial and fungal infections, being effective against some Gram-positive bacteria (notably Staphylococcus species) and some pathogenic fungi (including Candida species) but use declined following reports of animal carcinogenicity. It has also been used for dying wood, silk, and paper, as well as a histological stain.	2.41	1	0	organic chloride salt	anthelminthic drug; antibacterial agent; antifungal agent; antiseptic drug; histological dye
resazurin resazurin: used as indicator in detection of hyposulfite (sulfoxylate); in food research (reductase test); structure	2.1	1	0	phenoxazine
hematoporphyrin Hematoporphyrins: Iron-free derivatives of heme with 4 methyl groups, 2 hydroxyethyl groups and 2 propionic acid groups attached to the pyrrole rings. Some of these PHOTOSENSITIZING AGENTS are used in the PHOTOTHERAPY of malignant NEOPLASMS.. hematoporphyrin : A dicarboxylic acid that is protoporphyrin in which the vinyl groups at positions 7 and 12 are replaced by 1-hydroxyethyl groups.	1.97	1	0
neutral red Neutral Red: A vital dye used as an indicator and biological stain. Various adverse effects have been observed in biological systems.. neutral red : A hydrochloride obtained by combining the free base of neutral red with one equivalent of hydrochloric acid. Neutral red acts as a pH indicator, changing from red to yellow between pH 6.8 and 8.0.	3.24	6	0	hydrochloride	acid-base indicator; dye; two-colour indicator
lithium carbonate Lithium Carbonate: A lithium salt, classified as a mood-stabilizing agent. Lithium ion alters the metabolism of BIOGENIC MONOAMINES in the CENTRAL NERVOUS SYSTEM, and affects multiple neurotransmission systems.	1.96	1	0	carbonate salt; lithium salt	antimanic drug
glycidol glycidol: structure given in first source	2.44	2	0	epoxide; primary alcohol
diepoxybutane diepoxybutane: difunctional alkylating agent; RN given refers to cpd with unspecified isomeric designation; structure	2.71	3	0	epoxide	mutagen
7-hydroxymethyl-12-methylbenz(a)anthracene [no description available]	1.97	1	0	phenanthrenes
1,4-dimethylnaphthalene 1,4-dimethylnaphthalene : A dimethylnaphthalene carrying methyl groups at positions 1 and 4.	2.04	1	0	dimethylnaphthalene
docusate Dioctyl Sulfosuccinic Acid: All-purpose surfactant, wetting agent, and solubilizer used in the drug, cosmetics, and food industries. It has also been used in laxatives and as cerumenolytics. It is usually administered as either the calcium, potassium, or sodium salt.	2.15	1	0	diester; organosulfonic acid
3-hydroxyflavone 3-hydroxyflavone: structure given in first source. flavonol : A monohydroxyflavone that is the 3-hydroxy derivative of flavone.	5.95	7	1	flavonols; monohydroxyflavone
2,6-dimethylnaphthalene 2,6-dimethylnaphthalene: RN given refers to parent cpd. 2,6-dimethylnaphthalene : A dimethylnaphthalene carrying methyl groups at positions 2 and 6.	3.8	4	0	dimethylnaphthalene	environmental contaminant
anatabine anatabine: alkaloid found in tobacco; structure	1.96	1	0	bipyridines
1,2-dibromobenzene dibromobenzene : Any member of the class of bromobenzenes that consists of a benzene or a substituted benzene ring carrying two bromo groups at unspecified positions.	2.04	1	0	dibromobenzene
toluene 2,4-diisocyanate Toluene 2,4-Diisocyanate: Skin irritant and allergen used in the manufacture of polyurethane foams and other elastomers.. toluene 2,4-diisocyanate : A toluene meta-diisocyanate in which the isocyanato groups are at positions 2 and 4 relative to the methyl group on the benzene ring.	2.25	1	0	toluene meta-diisocyanate	allergen; hapten
diphenylamine Diphenylamine: In humans it may be irritating to mucous membranes. Methemoglobinemia has been produced experimentally. In veterinary use, it is one of active ingredients in topical agents for prevention and treatment of screwworm infestation. An indicator in tests for nitrate poisoning.. diphenylamine : An aromatic amine containing two phenyl substituents. It has been used as a fungicide for the treatment of superficial scald in apples and pears, but is no longer approved for this purpose within the European Union.	4.9	1	1	aromatic amine; bridged diphenyl fungicide; secondary amino compound	antifungal agrochemical; antioxidant; carotogenesis inhibitor; EC 1.3.99.29 [phytoene desaturase (zeta-carotene-forming)] inhibitor; ferroptosis inhibitor; radical scavenger
iodobenzene iodobenzene: RN given refers to unlabeled parent cpd	2.04	1	0
methyl n-butyl ketone Methyl n-Butyl Ketone: An industrial solvent which causes nervous system degeneration. MBK is an acronym often used to refer to it.. hexanone : A ketone that is a hexane carrying an oxo substituent at unspecified position.	2.02	1	0	ketone
1-hexene 1-hexene: structure in first source. 1-hexene : An alkene that is hexane carrying a double bond at position 1.	2.04	1	0	alkene
allyl sulfide allyl sulfide: essence of garlic; inhibits CYP2E1	3.78	11	0	organic sulfide
octadecane octadecane: RN given refers to parent cpd. octadecane : A straight-chain alkane carrying 18 carbon atoms.	1.96	1	0	long-chain alkane	bacterial metabolite; plant metabolite
9-nitroanthracene 9-nitroanthracene: RN given refers to cpd with locant for nitro moiety in 5 position	2.52	2	0	anthracenes
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).	6.61	67	0	extended flavonoid; naphtho-gamma-pyrone; organic heterotricyclic compound	aryl hydrocarbon receptor agonist; aryl hydrocarbon receptor antagonist; EC 1.14.14.14 (aromatase) inhibitor
1,3-indandione 1,3-indandione : A member of the class of indanones that is indane in which the hydrogens at positions 2 and 4 have been replaced by oxo groups.	1.97	1	0	aromatic ketone; beta-diketone; indanones
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.	4.03	14	0	nitroarene	carcinogenic agent; mutagen
pentachlorobenzene pentachlorobenzene: structure. pentachlorobenzene : A member of the class of pentachlorobenzenes that is benzene in which five of the hydrogens are replaced by chlorines. Now classed as a persistent organic pollutant under the Stockholm Convention.	2.04	1	0	pentachlorobenzenes	persistent organic pollutant
1-methylanthracene 1-methylanthracene: structure given in first source	2.46	2	0
1-aminoanthracene [no description available]	2.38	2	0	anthracenamine
2-methylanthracene 2-methylanthracene: structure given in first source	2.04	1	0
2-anthramine 2-anthramine: structure	5	40	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.	9.46	22	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
n-nitroso(di-n-propyl)amine [no description available]	1.99	1	0	nitroso compound
dimethyl disulfide [no description available]	2.13	1	0	organic disulfide	xenobiotic metabolite
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.	1.97	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.	2.68	3	0	organic disulfide	plant metabolite
c.i. 42510 Rosaniline Dyes: Compounds that contain the triphenylmethane aniline structure found in rosaniline. Many of them have a characteristic magenta color and are used as COLORING AGENTS.. basic fuchsin : A four-component mixture of chemically related dyes comprising pararosanilin, rosanilin, magenta II and new fuchsin in varying amounts. rosanilin : A hydrochloride that is the monohydrochloride of 4-[(4-aminophenyl)(4-iminocyclohexa-2,5-dien-1-ylidene)methyl]-2-methylaniline. One of the major constituents of Basic fuchsin, together with pararosanilin, magenta II and new fuchsin.	2	1	0
1,2,3,4-tetrachlorobenzene 1,2,3,4-tetrachlorobenzene : A tetrachlorobenzene carrying chloro groups at positions 1, 2 , 3 and 4.. tetrachlorobenzene : Any member of the class of chlorobenzenes carrying four chloro groups at unspecified positions.	2.04	1	0	tetrachlorobenzene
1,2,3,5-tetrachlorobenzene 1,2,3,5-tetrachlorobenzene : A tetrachlorobenzene carrying chloro groups at positions 1, 2, 3 and 5.	2.04	1	0	tetrachlorobenzene
erythromycin Erythromycin: A bacteriostatic antibiotic macrolide produced by Streptomyces erythreus. Erythromycin A is considered its major active component. In sensitive organisms, it inhibits protein synthesis by binding to 50S ribosomal subunits. This binding process inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins.. erythromycin : Any of several wide-spectrum macrolide antibiotics obtained from actinomycete Saccharopolyspora erythraea (formerly known as Streptomyces erythraeus).. erythromycin A : An erythromycin that consists of erythronolide A having 2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl and 3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl residues attahced at positions 4 and 6 respectively.	7.41	2	0	cyclic ketone; erythromycin
precocene ii precocene II: has antibacterial, antifungal, insecticidal, and antioxidant activities; from plants of genus Ageratum; an antiallotropin compound capable of inhibiting juvenile hormone biosynthesis	3.06	1	0	chromenes	precocenes
2'-deoxy-5'-adenosine monophosphate 2'-deoxy-5'-adenosine monophosphate: RN given refers to parent cpd. 2'-deoxyadenosine 5'-monophosphate : A purine 2'-deoxyribonucleoside 5'-monophosphate having adenine as the nucleobase.	1.98	1	0	2'-deoxyadenosine 5'-phosphate; purine 2'-deoxyribonucleoside 5'-monophosphate	fundamental metabolite
2-piperidone 2-piperidone: structure given in first source. piperidin-2-one : A delta-lactam that is piperidine which is substituted by an oxo group at position 2.	1.97	1	0	delta-lactam; piperidones	EC 1.2.1.88 (L-glutamate gamma-semialdehyde dehydrogenase) inhibitor
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.	4.51	24	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.	6.17	25	0	N-nitrosoureas	alkylating agent; carcinogenic agent; genotoxin; mutagen
9-methylanthracene [no description available]	2.78	3	0
9,10-dimethylanthracene 9,10-dimethylanthracene: RN given refers to parent ion	2.41	2	0
2-nitropyrene [no description available]	1.98	1	0	pyrenes
4-nitrophenyl acetate [no description available]	3.28	2	0	C-nitro compound; phenyl acetates
1-methylphenanthrene 1-methylphenanthrene: structure in first source. 1-methylphenanthrene : A member of the class of phenanthrenes that is phenanthrene substituted by a methyl group at position 1.	2.04	1	0	phenanthrenes	mutagen
terbutryne terbutryn : A methylthio-1,3,5-triazine that is 2-(methylsulfanyl)-1,3,5-triazine substituted by a tert-butylamino and an ethylamino group at positions 2 and 4 respectively.	2.03	1	0	diamino-1,3,5-triazine; methylthio-1,3,5-triazine	environmental contaminant; herbicide; xenobiotic
3-nitrofluoranthene 3-nitrofluoranthene: environmental carcinogen from diesel exhaust	2.68	3	0	nitronaphthalene
amaranth dye Amaranth Dye: A sulfonic acid-based naphthylazo dye used as a coloring agent for foodstuffs and medicines and as a dye and chemical indicator. It was banned by the FDA in 1976 for use in foods, drugs, and cosmetics. (From Merck Index, 11th ed)	1.97	1	0
hexafluoroisopropanol 1,1,1,3,3,3-hexafluoropropan-2-ol : An organofluorine compound formed by substitution of all the methyl protons in propan-2-ol by fluorine. It is a metabolite of inhalation anesthetic sevoflurane.	2.03	1	0	organofluorine compound; secondary alcohol	drug metabolite
dibutylnitrosamine dibutylnitrosamine: structure	1.99	1	0	nitroso compound
3,4-epoxy-1-butene 3,4-epoxy-1-butene: RN given refers to monomer	2.03	1	0
n-nitrosopyrrolidine N-Nitrosopyrrolidine: Carcinogenic nitrosamine that may be formed from preservatives in meats during their preparation or in the liver during metabolism.	2.7	3	0	pyrrolidines
nitrosobenzylmethylamine nitrosobenzylmethylamine: structure	1.97	1	0
9-aminophenanthrene [no description available]	1.97	1	0	phenanthrenamine
2'-deoxyadenosine 2'-deoxyformycin A: RN not in Chemline 9/85; RN and structure given in first source	2.02	1	0	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
n-nitrosodiethanolamine [no description available]	2	1	0	nitroso compound
undecane undecane : A straight-chain alkane with 11 carbon atoms.	2.39	2	0	alkane
1,3-propane sultone 1,3-propane sultone: sultone is usually defined as a derivative of 1,8-naphtholsulfonic acid; structure	1.98	1	0	sultone
decabromobiphenyl ether decabromobiphenyl ether: a flame retardant. decabromodiphenyl ether : A polybromodiphenyl ether that is diphenyl ether in which all of the hydrogens have been replaced by bromines.	2.11	1	0	polybromodiphenyl ether	neurotoxin
carmine Carmine: Coloring matter from the insect Coccus cacti L. It is used in foods, pharmaceuticals, toiletries, etc., as a dye, and also has use as a microscopic stain and biological marker.	2.01	1	0
durapatite Durapatite: The mineral component of bones and teeth; it has been used therapeutically as a prosthetic aid and in the prevention and treatment of osteoporosis.. hydroxylapatite : A phosphate mineral with the formula Ca5(PO4)3(OH).	1.95	1	0
zinc oxide Zinc Oxide: A mild astringent and topical protectant with some antiseptic action. It is also used in bandages, pastes, ointments, dental cements, and as a sunblock.	3.29	5	0	zinc molecular entity
arsenic trioxide Arsenic Trioxide: An inorganic compound with the chemical formula As2O3 that is used for the treatment of ACUTE PROMYELOCYTIC LEUKEMIA in patients who have relapsed from, or are resistant to, conventional drug therapy.	7.68	3	0
hydrofluoric acid Hydrofluoric Acid: Hydrofluoric acid. A solution of hydrogen fluoride in water. It is a colorless fuming liquid which can cause painful burns.. hydrogen fluoride : A diatomic molecule containing covalently bonded hydrogen and fluorine atoms.. organofluorine compound : An organofluorine compound is a compound containing at least one carbon-fluorine bond.	1.96	1	0	hydrogen halide; mononuclear parent hydride	NMR chemical shift reference compound
ferrous oxide [no description available]	3.09	1	0	iron oxide
glycyrrhizic acid glycyrrhizinic acid : A triterpenoid saponin that is the glucosiduronide derivative of 3beta-hydroxy-11-oxoolean-12-en-30-oic acid.	7.07	1	0	enone; glucosiduronic acid; pentacyclic triterpenoid; tricarboxylic acid; triterpenoid saponin	EC 3.4.21.5 (thrombin) inhibitor; plant metabolite
d-alpha tocopherol Vitamin E: A generic descriptor for all TOCOPHEROLS and TOCOTRIENOLS that exhibit ALPHA-TOCOPHEROL activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of ISOPRENOIDS.. tocopherol : A collective name for a group of closely related lipids that contain a chroman-6-ol nucleus substituted at position 2 by a methyl group and by a saturated hydrocarbon chain consisting of three isoprenoid units. They are designated as alpha-, beta-, gamma-, and delta-tocopherol depending on the number and position of additional methyl substituents on the aromatic ring. Tocopherols occur in vegetable oils and vegetable oil products, almost exclusively with R,R,R configuration. Tocotrienols differ from tocopherols only in having three double bonds in the hydrocarbon chain.. vitamin E : Any member of a group of fat-soluble chromanols that exhibit biological activity against vitamin E deficiency. The vitamers in this class consists of a chroman-6-ol core which is substituted at position 2 by a methyl group and (also at position 2) either a saturated or a triply-unsaturated hydrocarbon chain consisting of three isoprenoid units. The major function of vitamin E is to act as a natural antioxidant by scavenging free radicals and molecular oxygen.. (R,R,R)-alpha-tocopherol : An alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils.	7.6	44	1	alpha-tocopherol	algal metabolite; antiatherogenic agent; anticoagulant; antioxidant; antiviral agent; EC 2.7.11.13 (protein kinase C) inhibitor; immunomodulator; micronutrient; nutraceutical; plant metabolite
tocopherols [no description available]	4.05	4	0
pregnenolone carbonitrile Pregnenolone Carbonitrile: A catatoxic steroid and microsomal enzyme inducer having significant effects on the induction of cytochrome P450. It has also demonstrated the potential for protective capability against acetaminophen-induced liver damage.	3.07	5	0	aliphatic nitrile
selenomethionine [no description available]	2	1	0	selenoamino acid; selenomethionines	plant metabolite
1-aminopyrene [no description available]	2.38	2	0
butanesultone [no description available]	2.51	2	0
6-methylchrysene 6-methylchrysene: RN given refers to parent cpd; structure given in first source	2.04	1	0	carbopolycyclic compound
decane decane : A straight-chain alkane with 10 carbon atoms.	2.4	2	0	alkane
2,3,7,8-tetrachlorodibenzodioxine Tetrachlorodibenzodioxin: A mixture of isomers.	2.49	2	0	polychlorinated dibenzodioxine
tetrachloroisophthalonitrile tetrachloroisophthalonitrile: structure. chlorothalonil : A dinitrile that is benzene-1,3-dicarbonitrile substituted by four chloro groups. A non-systemic fungicide first introduced in the 1960s, it is used to control a range of diseases in a wide variety of crops.	2.42	2	0	aromatic fungicide; dinitrile; tetrachlorobenzene	antifungal agrochemical
paraquat Paraquat: A poisonous dipyridilium compound used as contact herbicide. Contact with concentrated solutions causes irritation of the skin, cracking and shedding of the nails, and delayed healing of cuts and wounds.. paraquat : An organic cation that consists of 4,4'-bipyridine bearing two N-methyl substituents loctated at the 1- and 1'-positions.	4.38	6	0	organic cation	geroprotector; herbicide
2'-deoxyadenosine triphosphate 2'-deoxyadenosine triphosphate: RN given refers to unlabeled parent cpd	2.44	2	0	2'-deoxyadenosine 5'-phosphate; purine 2'-deoxyribonucleoside 5'-triphosphate	Escherichia coli metabolite; mouse metabolite
2-tert-butylhydroquinone 2-tert-butylhydroquinone: an anticarcinogenic and chemopreventive agent. 2-tert-butylhydroquinone : A member of the class of hydroquinones in which one of the ring hydrogens of hydroquinone is replaced by a tert-butyl group.	2.76	3	0	hydroquinones	food antioxidant
dronabinol Dronabinol: A psychoactive compound extracted from the resin of Cannabis sativa (marihuana, hashish). The isomer delta-9-tetrahydrocannabinol (THC) is considered the most active form, producing characteristic mood and perceptual changes associated with this compound.. Delta(9)-tetrahydrocannabinol : A diterpenoid that is 6a,7,8,10a-tetrahydro-6H-benzo[c]chromene substituted at position 1 by a hydroxy group, positions 6, 6 and 9 by methyl groups and at position 3 by a pentyl group. The principal psychoactive constituent of the cannabis plant, it is used for treatment of anorexia associated with AIDS as well as nausea and vomiting associated with cancer chemotherapy.	1.96	1	0	benzochromene; diterpenoid; phytocannabinoid; polyketide	cannabinoid receptor agonist; epitope; hallucinogen; metabolite; non-narcotic analgesic
methionine sulfoximine methionine sulfoximine : A non-proteinogenic alpha-amino acid that is the sulfoximine derivative of methionine .	1.98	1	0	methionine derivative; non-proteinogenic alpha-amino acid; sulfoximide
amiloride Amiloride: A pyrazine compound inhibiting SODIUM reabsorption through SODIUM CHANNELS in renal EPITHELIAL CELLS. This inhibition creates a negative potential in the luminal membranes of principal cells, located in the distal convoluted tubule and collecting duct. Negative potential reduces secretion of potassium and hydrogen ions. Amiloride is used in conjunction with DIURETICS to spare POTASSIUM loss. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p705). amiloride : A member of the class of pyrazines resulting from the formal monoacylation of guanidine with the carboxy group of 3,5-diamino-6-chloropyrazine-2-carboxylic acid.	2.02	1	0	aromatic amine; guanidines; organochlorine compound; pyrazines	diuretic; sodium channel blocker
3,3'-dichlorobiphenyl [no description available]	2.25	1	0
diallyl trisulfide [no description available]	8.39	7	0	organic trisulfide	anti-inflammatory agent; antilipemic drug; antineoplastic agent; antioxidant; antiprotozoal drug; apoptosis inducer; estrogen receptor antagonist; insecticide; platelet aggregation inhibitor; vasodilator agent
4-chlorobiphenyl 4-chlorobiphenyl : A monochlorobiphenyl carrying a chloro substituent at position 4.	2.41	2	0	monochlorobiphenyl
perillaldehyde perillaldehyde: from oil of Perillae herba; has neuropharmacological actions; RN given refers to cpd without isomeric designation; structure in Merck Index, 9th ed, #6956. perillyl aldehyde : An aldehyde that is cyclohex-1-ene-1-carbaldehyde substituted by a prop-1-en-2-yl group at position 4.	2.17	1	0	aldehyde; olefinic compound	human metabolite; mouse metabolite; volatile oil component
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.	8.61	9	0	organic disulfide	antifungal agent; antineoplastic agent; plant metabolite
molinate molinate : A member of the class of azepanes that is azepane in which the nitrogen is substituted by an (ethylsulfanyl)carbonyl group, -C(=O)SEt. A thiocarbamate herbicide not approved for use in the U.S. or European Union, it is used control grass weeds in rice paddies.	2.03	1	0	azepanes; monothiocarbamic ester	agrochemical; antispermatogenic agent; herbicide
octachloronaphthalene Perna: A genus of freshwater mussel in the family MYTILIDAE, class BIVALVIA. It is found in tropical and warm temperate coastal waters. Most species have green in their shells.	3.47	7	0
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.	5.69	15	0	isothiocyanate	antineoplastic agent; EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor; metabolite
1-methylpyrene [no description available]	2.25	1	0	pyrenes
6-methylbenzo(a)pyrene [no description available]	2.38	2	0
mirex Mirex: An organochlorine insecticide that is carcinogenic.	2.37	2	0	chlorocarbon; organochlorine insecticide	persistent organic pollutant
12-methylbenzanthracene [no description available]	2.04	1	0
quinomethionate quinomethionate: an ingredient of Morestan. quinomethionate : A dithioloquinoxaline that results from the formal condensation of 6-methylquinoxaline-2,3-dithiol with phosgene. It has been used as a fungicide and acaricide for the control of mites and powdery mildew on citrus, vegetables, and walnuts, but is not approved for use in the EU.	2.04	1	0	dithioloquinoxaline; quinoxaline acaricide; quinoxaline antifungal agent	agrochemical
2-methylphenanthrene [no description available]	2.04	1	0
7-methylbenzanthracene [no description available]	2.69	3	0
7,12-dihydroxymethylbenz(a)anthracene 7,12-dihydroxymethylbenz(a)anthracene: structure given in first source	2.93	4	0
uridine diphosphate glucuronic acid Uridine Diphosphate Glucuronic Acid: A nucleoside diphosphate sugar which serves as a source of glucuronic acid for polysaccharide biosynthesis. It may also be epimerized to UDP iduronic acid, which donates iduronic acid to polysaccharides. In animals, UDP glucuronic acid is used for formation of many glucosiduronides with various aglycones.. UDP-alpha-D-glucuronic acid : A UDP-sugar having alpha-D-glucuronic acid as the sugar component.	3.84	12	0	UDP-D-glucuronic acid	Escherichia coli metabolite; human metabolite; mouse metabolite
6-chrysenamine 6-chrysenamine: may cause splenic atrophy and leukopenia; minor descriptor (76-84); on-line & Index Medicus search PHENANTHRENES (76-84)	2.88	4	0	carbopolycyclic compound
benzo(a)pyrene-6,12-quinone benzo(a)pyrene-6,12-quinone: tautomerizes to the diol; structure	2.69	3	0
benzo(a)pyrene-1,6-quinone benzo(a)pyrene-1,6-quinone: RN given refers to parent cpd	3.25	6	0
benzo(a)pyrene-3,6-quinone [no description available]	3.08	5	0
trichloroepoxypropane Trichloroepoxypropane: A potent epoxide hydrase and aryl hydrocarbon hydroxylase inhibitor. It enhances the tumor-initiating ability of certain carcinogens.	3.58	9	0
octachlorodibenzo-4-dioxin octachlorodibenzo-4-dioxin: RN given refers to unlabeled parent cpd	1.97	1	0	polychlorinated dibenzodioxine
fluorescein-5-isothiocyanate Fluorescein-5-isothiocyanate: Fluorescent probe capable of being conjugated to tissue and proteins. It is used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.. fluorescein 5-isothiocyanate : The 5-isomer of fluorescein isothiocyanate. Acts as a fluorescent probe capable of being conjugated to tissue and proteins; used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.	2.69	3	0	fluorescein isothiocyanate
sabinene sabinene: RN given refers to cpd without isomeric designation. sabinene : A thujene that is a bicyclic monoterpene isolated from the essential oils of various plant species.	2.7	3	0	thujene	plant metabolite
dithiothreitol 1,4-dimercaptobutane-2,3-diol : A glycol that is butane-2,3-diol in which a hydrogen from each of the methyl groups is replaced by a thiol group.. 1,4-dithiothreitol : The threo-diastereomer of 1,4-dimercaptobutane-2,3-diol.	4.9	1	1	1,4-dimercaptobutane-2,3-diol; butanediols; dithiol; glycol; thiol	chelator; human metabolite; reducing agent
3-methoxy-4-aminoazobenzene [no description available]	1.99	1	0
furaneol furaneol: RN given refers to compound with no isomeric designation. 4-hydroxy-2,5-dimethylfuran-3-one : A member of the class of furans that is 2,5-dimethylfuran carrying additional oxo and hydroxy groups at positions 3 and 4 respectively. It has been found particularly in strawberries and other such fruits.	1.99	1	0	cyclic ketone; enol; furans	flavouring agent; fragrance; plant metabolite
5-methylchrysene 5-methylchrysene: methylchrysenes in tobacco smoke are suspected to contribute to tumorigenicity of this inhalant; RN given refers to unlabeled cpd; structure	3.4	7	0	carbopolycyclic compound
5,6-dimethylchrysene 5,6-dimethylchrysene: structure given in first source	2.04	1	0
7-ethylbenz(a)anthracene [no description available]	2.04	1	0
n,n-diethylhydroxylamine N,N-diethylhydroxylamine: RN given refers to parent cpd	1.96	1	0
nafenopin Nafenopin: A peroxisome proliferator that is used experimentally to promote liver tumors. It has been used as an antihyperlipoproteinemic agent.. nafenopin : A racemate comprising equimolar amounts of (R)- and (S)-nafenopin. It is a peroxisome proliferator that is used experimentally to promote liver tumors. It has been used as an hypolipidemic agent.. 2-methyl-2-[4-(1,2,3,4-tetrahydronaphthalen-1-yl)phenoxy]propanoic acid : A monocarboxylic acid that is 2-hydroxy-2-methylpropanoic acid in which ther tertiary hydroxy group has been converted into the corresponding p-(1,2,3,4-tetrahydronaphthalen-1-yl)phenyl ether.	1.96	1	0	aromatic ether; monocarboxylic acid
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.	3.11	5	0	diastereoisomeric mixture; homocysteines; non-proteinogenic alpha-amino acid; sulfoximide	EC 6.3.2.2 (glutamate--cysteine ligase) inhibitor; ferroptosis inducer
1'-hydroxysafrole [no description available]	1.96	1	0
1-hydroxypyrene 1-hydroxypyrene: pyrene metabolite; RN given refers to parent cpd	4.97	37	0	pyrenes
1,3-diphenylisobenzofuran 1,3-diphenylisobenzofuran: quencher of singlet oxygen, inhibits arachidonic acid induced platelet aggregation	3.05	1	0
1-nitropyrene [no description available]	6.01	36	0	nitroarene	carcinogenic agent
o,o-diethyl o-3,5,6-trichloro-2-pyridyl phosphate [no description available]	2	1	0
iodinated glycerol iodinated glycerol: secretolytic agent; RN given refers to cpd without iodine locant	1.98	1	0	dioxolane
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.	2.68	3	0	2-acetamidofluorenes	carcinogenic agent; mutagen
3-thiophene acetic acid 3-thiophene acetic acid: structure in first source	2.6	1	0
2,4,4'-trichlorobiphenyl [no description available]	2.02	1	0
nitrosocarbaryl nitrosocarbaryl: combination of food additive sodium nitrite with carbaryl (SEVIN) results in formation of acid solution of potent mutagen; RN given refers to unlabeled parent cpd. nitrosocarbaryl : A nitroso compound that is carbaryl in which the amino hydrogen is substituted by a nitroso group.	1.96	1	0	carbamate ester; naphthalenes; nitroso compound	carcinogenic agent; mutagen
1-phenyl-3,3-dimethyltriazene [no description available]	1.96	1	0
manganese Manganese: A trace element with atomic symbol Mn, atomic number 25, and atomic weight 54.94. It is concentrated in cell mitochondria, mostly in the pituitary gland, liver, pancreas, kidney, and bone, influences the synthesis of mucopolysaccharides, stimulates hepatic synthesis of cholesterol and fatty acids, and is a cofactor in many enzymes, including arginase and alkaline phosphatase in the liver. (From AMA Drug Evaluations Annual 1992, p2035). manganese(4+) : A manganese cation that is monoatomic and has a formal charge of +4.	8.37	7	0	elemental manganese; manganese group element atom	Escherichia coli metabolite; micronutrient
mercury Mercury: A silver metallic element that exists as a liquid at room temperature. It has the atomic symbol Hg (from hydrargyrum, liquid silver), atomic number 80, and atomic weight 200.59. Mercury is used in many industrial applications and its salts have been employed therapeutically as purgatives, antisyphilitics, disinfectants, and astringents. It can be absorbed through the skin and mucous membranes which leads to MERCURY POISONING. Because of its toxicity, the clinical use of mercury and mercurials is diminishing.. mercury(0) : Elemental mercury of oxidation state zero.	9.22	5	0	elemental mercury; zinc group element atom	neurotoxin
molybdenum Molybdenum: A metallic element with the atomic symbol Mo, atomic number 42, and atomic weight 95.95. It is an essential trace element, being a component of the enzymes xanthine oxidase, aldehyde oxidase, and nitrate reductase.	2.66	3	0	chromium group element atom	micronutrient
palladium Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.	2.72	3	0	metal allergen; nickel group element atom; platinum group metal atom
platinum Platinum: A heavy, soft, whitish metal, resembling tin, with atomic number 78, atomic weight 195.084, symbol Pt. It is used in manufacturing equipment for laboratory and industrial use. It occurs as a black powder (platinum black) and as a spongy substance (spongy platinum) and may have been known in Pliny's time as alutiae.	3.52	2	0	elemental platinum; nickel group element atom; platinum group metal atom
plutonium Plutonium: A naturally radioactive element of the actinide metals series. It has the atomic symbol Pu, and atomic number 94. Plutonium is used as a nuclear fuel, to produce radioisotopes for research, in radionuclide batteries for pacemakers, and as the agent of fission in nuclear weapons.	1.96	1	0	actinoid atom; f-block element atom
ruthenium Ruthenium: A hard, brittle, grayish-white rare earth metal with an atomic symbol Ru, atomic number 44, and atomic weight 101.07. It is used as a catalyst and hardener for PLATINUM and PALLADIUM.	5.05	2	1	iron group element atom; platinum group metal atom
silver Silver: An element with the atomic symbol Ag, atomic number 47, and atomic weight 107.87. It is a soft metal that is used medically in surgical instruments, dental prostheses, and alloys. Long-continued use of silver salts can lead to a form of poisoning known as ARGYRIA.	6.04	4	1	copper group element atom; elemental silver	Escherichia coli metabolite
titanium Titanium: A dark-gray, metallic element of widespread distribution but occurring in small amounts with atomic number, 22, atomic weight, 47.867 and symbol, Ti; specific gravity, 4.5; used for fixation of fractures.	5.83	6	1	titanium group element atom
cadmium Cadmium: An element with atomic symbol Cd, atomic number 48, and atomic weight 112.41. It is a metal and ingestion will lead to CADMIUM POISONING.. elemental cadmium : An element in the zinc group of the periodic table with atomic number 48, atomic mass 112, M.P. 321degreeC, and B.P. 765degreeC). An odourless, tasteless, and highly poisonous soft, ductile, lustrous metal with electropositive properties. It has eight stable isotopes: (106)Cd, (108)Cd,(110)Cd, (111)Cd, (112)Cd, (113)Cd, (114)Cd and (116)Cd, with (112)Cd and (114)Cd being the most common.	7.71	63	0	cadmium molecular entity; zinc group element atom
cerium Cerium: An element of the rare earth family of metals. It has the atomic symbol Ce, atomic number 58, and atomic weight 140.12. Cerium is a malleable metal used in industrial applications.	2.83	3	0	f-block element atom; lanthanoid atom
chromium Chromium: A trace element that plays a role in glucose metabolism. It has the atomic symbol Cr, atomic number 24, and atomic weight 52. According to the Fourth Annual Report on Carcinogens (NTP85-002,1985), chromium and some of its compounds have been listed as known carcinogens.. chromium ion : An chromium atom having a net electric charge.. chromium atom : A chromium group element atom that has atomic number 24.	9.17	16	0	chromium group element atom; metal allergen	micronutrient
gold Gold: A yellow metallic element with the atomic symbol Au, atomic number 79, and atomic weight 197. It is used in jewelry, goldplating of other metals, as currency, and in dental restoration. Many of its clinical applications, such as ANTIRHEUMATIC AGENTS, are in the form of its salts.	3.67	8	0	copper group element atom; elemental gold
uranium Uranium: A radioactive element of the actinide series of metals. It has an atomic symbol U, atomic number 92, and atomic weight 238.03. U-235 is used as the fissionable fuel in nuclear weapons and as fuel in nuclear power reactors.	3.25	1	0	actinoid atom; f-block element atom; monoatomic uranium
vanadium Vanadium: A metallic element with the atomic symbol V, atomic number 23, and atomic weight 50.94. It is used in the manufacture of vanadium steel. Prolonged exposure can lead to chronic intoxication caused by absorption usually via the lungs.	1.97	1	0	elemental vanadium; vanadium group element atom	micronutrient
yttrium Yttrium: An element of the rare earth family of metals. It has the atomic symbol Y, atomic number 39, and atomic weight 88.91. In conjunction with other rare earths, yttrium is used as a phosphor in television receivers and is a component of the yttrium-aluminum garnet (YAG) lasers.	2.02	1	0	d-block element atom; rare earth metal atom; scandium group element atom
zirconium Zirconium: A rather rare metallic element with atomic number 40, atomic weight 91.224, and symbol Zr.	2.02	1	0	titanium group element atom
cupric chloride cupric chloride: RN given refers to unlabeled parent cpd. copper(II) chloride : An inorganic chloride of copper in which the metal is in the +2 oxidation state.	2.03	1	0	copper molecular entity; inorganic chloride	EC 5.3.3.5 (cholestenol Delta-isomerase) inhibitor
mercuric chloride Mercuric Chloride: Mercury chloride (HgCl2). A highly toxic compound that volatizes slightly at ordinary temperature and appreciably at 100 degrees C. It is corrosive to mucous membranes and used as a topical antiseptic and disinfectant.. mercury dichloride : A mercury coordination entity made up of linear triatomic molecules in which a mercury atom is bonded to two chlorines. Water-soluble, it is highly toxic. Once used in a wide variety of applications, including preserving wood and anatomical specimens, embalming and disinfecting, as an intensifier in photography, as a mordant for rabbit and beaver furs, and freeing gold from lead, its use has markedly declined as less toxic alternatives have been developed.	2.03	1	0	mercury coordination entity	sensitiser
6-nitrochrysene 6-nitrochrysene: RN given refers to cpd with locant for nitro group in position 6	3.7	10	0	carbopolycyclic compound
galactosamine 2-amino-2-deoxy-D-galactopyranose : The pyranose form of D-galactosamine.. D-galactosamine : The D-stereoisomer of galactosamine.	1.97	1	0	D-galactosamine; primary amino compound	toxin
camptothecin NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source	5.2	2	1	delta-lactone; pyranoindolizinoquinoline; quinoline alkaloid; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor; genotoxin; plant metabolite
ferric chloride ferric chloride: RN given refers to cpd with MF of Fe-Cl3; used to induce experimental arterial thrombosis to evaluate antithrombotic agents	1.96	1	0	iron coordination entity	astringent; Lewis acid
nickel chloride nickel chloride: RN given refers to cpd with MF of Ni-Cl2. nickel dichloride : A compound of nickel and chloride in which the ratio of nickel (in the +2 oxidation state) to chloride is 1:2.	8.09	5	0	nickel coordination entity	calcium channel blocker; hapten
ferrous sulfate ferrous sulfate: Ferro-Gradumet is ferrous sulfate in controlled release form; RN given refers to Fe(+2)[1:1] salt. iron(2+) sulfate (anhydrous) : A compound of iron and sulfate in which the ratio of iron(2+) to sulfate ions is 1:1. Various hydrates occur naturally - most commonly the heptahydrate, which loses water to form the tetrahydrate at 57degreeC and the monohydrate at 65degreeC.	2.03	1	0	iron molecular entity; metal sulfate	reducing agent
sodium sulfite [no description available]	1.97	1	0	inorganic sodium salt; sulfite salt	food preservative; reducing agent
calcium phosphate, dibasic, anhydrous calcium phosphate, dibasic, anhydrous: molecular formula CaHPO(4), DCPA=dicalcium phosphate anhydrous; don't confuse with dichloropropionanilide which also is called DCPA; MW=136.06; has greater surface area and lower pH than DCPD (dicalcium phosphate dihydrate); occurs in nature as monetite; an intermediate in preparing hydroxyapatite	1.98	1	0	calcium phosphate
calcium phosphate, monobasic, anhydrous calcium phosphate, monobasic: MW 234.05	1.98	1	0	calcium phosphate	fertilizer
tricalcium phosphate tricalcium phosphate: a form of tricalcium phosphate used as bioceramic bone replacement material; see also records for alpha-tricalcium phosphate, beta-tricalcium phosphate, calcium phosphate; apatitic tricalcium phosphate Ca9(HPO4)(PO4)5(OH) is the calcium orthophosphate leading to beta tricalcium phosphate Ca3(PO4)2 (b-TCP). calcium phosphate : A calcium salt composed of calcium and phosphate/diphosphate ions; present in milk and used for the mineralisation of calcified tissues.	1.98	1	0	calcium phosphate
lead chromate lead chromate: RN given refers to unspecified lead chromate. lead chromate : A chromium coordination entity comprising chromate and lead(2+) ions in a 1:1 ratio	1.96	1	0	chromium coordination entity; lead coordination entity	carcinogenic agent; nephrotoxin; neurotoxin
chromates Chromates: Salts of chromic acid containing the CrO(2-)4 radical.. chromate(2-) : A chromium oxoanion resulting from the removal of two protons from chromic acid.	3.37	7	0	chromium oxoanion; divalent inorganic anion	oxidising agent
copper sulfate Copper Sulfate: A sulfate salt of copper. It is a potent emetic and is used as an antidote for poisoning by phosphorus. It also can be used to prevent the growth of algae.. copper(II) sulfate : A metal sulfate compound having copper(2+) as the metal ion.	3.25	6	0	metal sulfate	emetic; fertilizer; sensitiser
potassium dichromate Potassium Dichromate: Chromic acid (H2Cr2O7), dipotassium salt. A compound having bright orange-red crystals and used in dyeing, staining, tanning leather, as bleach, oxidizer, depolarizer for dry cells, etc. Medically it has been used externally as an astringent, antiseptic, and caustic. When taken internally, it is a corrosive poison.. potassium dichromate : A potassium salt that is the dipotassium salt of dichromic acid.	2.9	4	0	potassium salt	allergen; oxidising agent; sensitiser
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	2.02	1	0	dihydrogen
fluorine Fluorine: A nonmetallic, diatomic gas that is a trace element and member of the halogen family. It is used in dentistry as fluoride (FLUORIDES) to prevent dental caries.	2.93	4	0	diatomic fluorine; gas molecular entity	NMR chemical shift reference compound
chlorine Chlorine: An element with atomic symbol Cl, atomic number 17, and atomic weight 35, and member of the halogen family.	1.97	1	0	diatomic chlorine; gas molecular entity	bleaching agent
nitrous acid Nitrous Acid: Nitrous acid (HNO2). A weak acid that exists only in solution. It can form water-soluble nitrites and stable esters. (From Merck Index, 11th ed)	1.96	1	0	nitrogen oxoacid
nickel sulfate nickel sulfate: RN given refers to cpd with MF of Ni(2+)-H2SO4. nickel sulfate : A metal sulfate having nickel(2+) as the metal ion.	2.89	4	0	metal sulfate	allergen
potassium chromate(vi) potassium chromate(VI): RN given refers to cpd with MF of K2-CrH2O4. potassium chromate : A potassium salt consisting of potassium and chromate ions in a 2:1 ratio.	2.37	2	0	potassium salt	carcinogenic agent; oxidising agent
deuterium oxide Deuterium Oxide: The isotopic compound of hydrogen of mass 2 (deuterium) with oxygen. (From Grant & Hackh's Chemical Dictionary, 5th ed) It is used to study mechanisms and rates of chemical or nuclear reactions, as well as biological processes.	2.43	2	0	deuterated compound; water	NMR solvent
fluorosulfonic acid perfluorosulfonic acid: sulfonated tetrafluoroethylene-based fluoropolymer–copolymer	2.07	1	0	sulfur oxoacid	NMR solvent
molybdate ion molybdate : A divalent inorganic anion obtained by removal of both protons from molybdic acid	1.97	1	0	divalent inorganic anion; molybdenum oxoanion	Escherichia coli metabolite
galactose aldohexose : A hexose with a (potential) aldehyde group at one end.	2.74	3	0
poloxalene Poloxalene: A copolymer of polyethylene and polypropylene ether glycol. It is a non-ionic polyol surface-active agent used medically as a fecal softener and in cattle for prevention of bloat.. pluronic : A triblock copolymer composed of a central hydrophobic chain of poly(propylene oxide) flanked by two hydrophilic chains of poly(ethylene oxide).	2.39	2	0	epoxide
ozone Ozone: The unstable triatomic form of oxygen, O3. It is a powerful oxidant that is produced for various chemical and industrial uses. Its production is also catalyzed in the ATMOSPHERE by ULTRAVIOLET RAY irradiation of oxygen or other ozone precursors such as VOLATILE ORGANIC COMPOUNDS and NITROGEN OXIDES. About 90% of the ozone in the atmosphere exists in the stratosphere (STRATOSPHERIC OZONE).. ozone : An elemental molecule with formula O3. An explosive, pale blue gas (b.p. -112degreeC) that has a characteristic, pungent odour, it is continuously produced in the upper atmosphere by the action of solar ultraviolet radiation on atmospheric oxygen. It is an antimicrobial agent used in the production of bottled water, as well as in the treatment of meat, poultry and other foodstuffs.	7.74	21	1	elemental molecule; gas molecular entity; reactive oxygen species; triatomic oxygen	antiseptic drug; disinfectant; electrophilic reagent; greenhouse gas; mutagen; oxidising agent; tracer
radon Radon: A naturally radioactive element with atomic symbol Rn, and atomic number 86. It is a member of the noble gas family found in soil, and is released during the decay of RADIUM.. radon(0) : A monoatomic radon that has an oxidation state of zero.	1.96	1	0	monoatomic radon; noble gas atom; p-block element atom
lead nitrate lead nitrate: RN given refers to unspecified lead nitrate	2.44	2	0	inorganic nitrate salt; lead coordination entity
sodium selenite disodium selenite : An inorganic sodium salt composed of sodium and selenite ions in a 2:1 ratio.	2.39	2	0	inorganic sodium salt; selenite salt	nutraceutical
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.	8.89	12	0	cadmium coordination entity
cadmium sulfate cadmium sulfate: RN given refers to cpd with MF of Cd-H2SO4	2.9	4	0	cadmium salt
4-chloro-7-nitrobenzofurazan 4-Chloro-7-nitrobenzofurazan: A benzofuran derivative used as a protein reagent since the terminal N-NBD-protein conjugate possesses interesting fluorescence and spectral properties. It has also been used as a covalent inhibitor of both beef heart mitochondrial ATPase and bacterial ATPase.. 4-chloro-7-nitrobenzofurazan : A benzoxadiazole that is 2,1,3-benzoxadiazole which is substituted at position 4 by chlorine and at position 7 by a nitro group.	1.96	1	0	benzoxadiazole; C-nitro compound; organochlorine compound	EC 1.4.3.4 (monoamine oxidase) inhibitor; EC 3.6.1.3 (adenosinetriphosphatase) inhibitor; fluorescent probe; fluorochrome
n,n-naphthaloylhydroxylamine N,N-naphthaloylhydroxylamine: used for ultrahistochemical detection of Ca	1.97	1	0
sodium bichromate sodium bichromate: RN given refers to di-Na salt	2.91	4	0	inorganic sodium salt
carbendazim carbendazim: carcinogen when combined with sodium nitrite; principle metabolite of thiophanate methyl & benomyl; structure. carbendazim : A member of the class of benzimidazoles that is 2-aminobenzimidazole in which the primary amino group is substituted by a methoxycarbonyl group. A fungicide, carbendazim controls Ascomycetes, Fungi Imperfecti, and Basidiomycetes on a wide variety of crops, including bananas, cereals, cotton, fruits, grapes, mushrooms, ornamentals, peanuts, sugarbeet, soybeans, tobacco, and vegetables.	2.31	1	0	benzimidazole fungicide; benzimidazoles; benzimidazolylcarbamate fungicide; carbamate ester	antifungal agrochemical; antinematodal drug; metabolite; microtubule-destabilising agent
chrysotile Asbestos, Serpentine: A type of asbestos that occurs in nature as the dihydrate of magnesium silicate. It exists in two forms: antigorite, a plated variety, and chrysotile, a fibrous variety. The latter makes up 95% of all asbestos products. (From Merck Index, 11th ed, p.893)	4.16	17	0
ethionine L-ethionine : An S-ethylhomocysteine that has S-configuration at the chiral centre.	3.76	3	0	S-ethylhomocysteine	antimetabolite; carcinogenic agent
n-ethyl-n-hydroxyethylnitrosamine N-ethyl-N-(2-hydroxyethyl)nitrosamine : A nitrosamine that is N-nitrosodiethylamine in which one of the ethyl froups has been replaced by a 2-hydroxyethyl group. It is used to induce renal and liver tumours in rodents.	1.97	1	0	nitrosamine; primary alcohol	carcinogenic agent
2-nitrofluoranthene [no description available]	2.43	2	0
3-hydroxybenzo(a)pyrene 3-hydroxybenzo(a)pyrene: RN given refers to unlabeled parent cpd	7.5	40	1	ortho- and peri-fused polycyclic arene
benzo(a)pyrene 7,8-dihydrodiol benzo(a)pyrene 7,8-dihydrodiol: RN given refers to cpd without isomeric designation	6.77	80	0	pyrenes
titanium dioxide titanium dioxide: used medically as protectant against externally caused irritation & sunlight; high concentrations of dust may cause irritation to respiratory tract; RN given refers to titanium oxide (TiO2); structure. titanium dioxide : A titanium oxide with the formula TiO2. A naturally occurring oxide sourced from ilmenite, rutile and anatase, it has a wide range of applications.	3.02	4	0	titanium oxides	food colouring
beryllium sulfate beryllium sulfate: used as a diagnostic aid for allergic reactions in patients with fungal infection; RN given refers to (Be sulfate[1:1]). beryllium sulfate : A metal sulfate in which the metal is beryllium (in the +2 oxidation state) and the ratio of beryllium to sulfate is 1:1.	1.96	1	0	metal sulfate	allergen
tiletamine hydrochloride Cyclohexanones: Cyclohexane ring substituted by one or more ketones in any position.. cyclohexanones : Any alicyclic ketone based on a cyclohexane skeleton and its substituted derivatives thereof.	2.43	2	0
vinyl carbamate vinyl carbamate: promutagen & more carcinogenic analog of ethyl carbamate (urethane); structure	7.08	1	0	carbamate ester
cromolyn sodium Cromolyn Sodium: A chromone complex that acts by inhibiting the release of chemical mediators from sensitized MAST CELLS. It is used in the prophylactic treatment of both allergic and exercise-induced asthma, but does not affect an established asthmatic attack.. disodium cromoglycate : An organic sodium salt that is the disodium salt of cromoglycic acid.	1.96	1	0	organic sodium salt	anti-asthmatic drug; drug allergen
n'-nitrosonornicotine N'-nitrosonornicotine: structure; a potent carcinogen in laboratory animals	4	14	0	pyridines; pyrrolidines
tetradecanoylphorbol acetate Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.	7.49	98	0	acetate ester; diester; phorbol ester; tertiary alpha-hydroxy ketone; tetradecanoate ester	antineoplastic agent; apoptosis inducer; carcinogenic agent; mitogen; plant metabolite; protein kinase C agonist; reactive oxygen species generator
nickel sulfide nickel sulfide: RN given refers to cpd with MF of Ni-S; see also nickel subsulfide: 12035-72-2	1.96	1	0
fluorides [no description available]	4.33	6	0	halide anion; monoatomic fluorine
acridine half-mustard acridine half-mustard: RN given refers to parent cpd. acridine half-mustard : A member of the class of aminoacridines that is acridine which is substituted by a methoxy group at position 2, chlorine at position 6, and a {3-[(2-chloroethyl)amino]propyl}amino group at position 9.	3.09	5	0	aminoacridines; aromatic ether; organochlorine compound; secondary amino compound	mutagen
9-hydroxybenzo(a)pyrene 9-hydroxybenzo(a)pyrene: RN given refers to unlabeled parent cpd	4.58	8	0	ortho- and peri-fused polycyclic arene
7,8-dihydrobenzo(a)pyrene 7,8-dihydrobenzo(a)pyrene: structure given in first source	3.05	1	0
stilbene oxide stilbene oxide: inducer of epoxide hydratase; RN given refers to cpd without isomeric designation	3.08	5	0	epoxide
metizoline metizoline: RN given refers to parent cpd; structure	2.02	1	0	1-benzothiophenes
chromium chromium hexavalent ion: a human respiratory carcinogen	3.2	5	0	chromium cation; monoatomic hexacation
7-nitrobenzanthracene [no description available]	1.98	1	0	phenanthrenes
daunorubicin Daunorubicin: A very toxic anthracycline aminoglycoside antineoplastic isolated from Streptomyces peucetius and others, used in treatment of LEUKEMIA and other NEOPLASMS.. anthracycline : Anthracyclines are polyketides that have a tetrahydronaphthacenedione ring structure attached by a glycosidic linkage to the amino sugar daunosamine.. daunorubicin : A natural product found in Actinomadura roseola.	3.51	8	0	aminoglycoside antibiotic; anthracycline; p-quinones; tetracenequinones	antineoplastic agent; bacterial metabolite
6-(hydroxymethyl)benzo(a)pyrene 6-(hydroxymethyl)benzo(a)pyrene: RN given refers to parent cpd	1.95	1	0
4-nitrophenyl 4'-guanidinobenzoate 4-nitrophenyl 4'-guanidinobenzoate: kallikrein substrate; acrosin antagonist in sperm; serine esterase inhibitor; RN given refers to parent cpd; structure	1.96	1	0
2,6-diaminopurine 9H-purine-2,6-diamine : A member of the class of 2,6-diaminopurines that is 9H-purine in which the hydrogens at positions 2 and 6 are replaced by amino groups.	2.03	1	0	2,6-diaminopurines; primary amino compound	antineoplastic agent
bromocriptine Bromocriptine: A semisynthetic ergotamine alkaloid that is a dopamine D2 agonist. It suppresses prolactin secretion.	2.03	1	0	indole alkaloid	antidyskinesia agent; antiparkinson drug; dopamine agonist; hormone antagonist
3,9-dinitrofluoranthene [no description available]	2.69	3	0	nitronaphthalene
fenitrothion Fenitrothion: An organothiophosphate cholinesterase inhibitor that is used as an insecticide.. fenitrothion : An organic thiophosphate that is O,O-dimethyl O-phenyl phosphorothioate substituted by a methyl group at position 3 and a nitro group at position 4.	2.45	2	0	C-nitro compound; organic thiophosphate	acaricide; agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; insecticide
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	5.87	7	1	benzenes; phenyl acetates
phenoxyethanol phenoxyethanol: structure. 2-phenoxyethanol : An aromatic ether that is phenol substituted on oxygen by a 2-hydroxyethyl group.	2.31	1	0	aromatic ether; glycol ether; primary alcohol	antiinfective agent; central nervous system depressant
cetylpyridinium chloride anhydrous tserigel: according to first source contains polyvinylbutyral & cetylpyridinium chloride; UD only lists cetylpyridinium chloride as constituent. cetylpyridinium chloride : A pyridinium salt that has N-hexadecylpyridinium as the cation and chloride as the anion. It has antiseptic properties and is used in solutions or lozenges for the treatment of minor infections of the mouth and throat.	2.08	1	0	chloride salt; organic chloride salt	antiseptic drug; surfactant
myrcene myrcene: structure in first source. beta-myrcene : A monoterpene that is octa-1,6-diene bearing methylene and methyl substituents at positions 3 and 7 respectively.	2.42	2	0	monoterpene	anabolic agent; anti-inflammatory agent; flavouring agent; fragrance; plant metabolite; volatile oil component
isopentyl alcohol isopentyl alcohol: RN given refers to unlabeled parent cpd. isoamylol : An primary alcohol that is butan-1-ol in which a hydrogen at position 3 has been replaced by a methyl group.	2.02	1	0	alkyl alcohol; primary alcohol; volatile organic compound	antifungal agent; Saccharomyces cerevisiae metabolite; xenobiotic metabolite
acetylacetone acetylacetone : A beta-diketone that is pentane in which the hydrogens at positions 2 and 4 are replaced by oxo groups.	1.97	1	0	beta-diketone
sulfolane sulfolane : A member of the class of tetrahydrothiophenes that is tetrahydrothiophene in which the sulfur has been oxidised to give the corresponding sulfone. A colourless, high-boiling (285degreeC) liquid that is miscible with both water and hydrocarbons, it is used as an industrial solvent, particularly for the purification of hydrocarbon mixtures by liquid-vapour extraction.	2	1	0	sulfone; tetrahydrothiophenes	polar aprotic solvent
tetrachloroethylene Tetrachloroethylene: A chlorinated hydrocarbon used as an industrial solvent and cooling liquid in electrical transformers. It is a potential carcinogen.	3.1	5	0	chlorocarbon; chloroethenes	nephrotoxic agent
ursodeoxycholic acid Ursodeoxycholic Acid: An epimer of chenodeoxycholic acid. It is a mammalian bile acid found first in the bear and is apparently either a precursor or a product of chenodeoxycholate. Its administration changes the composition of bile and may dissolve gallstones. It is used as a cholagogue and choleretic.. ursodeoxycholic acid : A bile acid found in the bile of bears (Ursidae) as a conjugate with taurine. Used therapeutically, it prevents the synthesis and absorption of cholesterol and can lead to the dissolution of gallstones.. ursodeoxycholate : A bile acid anion that is the conjugate base of ursodeoxycholic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.	2	1	0	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
pyrene pyrene: structure in Merck Index, 9th ed, #7746. pyrene : An ortho- and peri-fused polycyclic arene consisting of four fused benzene rings, resulting in a flat aromatic system.	6.18	127	0	ortho- and peri-fused polycyclic arene	fluorescent probe; persistent organic pollutant
benzonidazole benzonidazole: used in treatment of Chagas' disease. benznidazole : A monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2-nitroimidazol-1-yl)acetic acid with the aromatic amino group of benzylamine. Used for treatment of Chagas disease.	2.25	1	0	C-nitro compound; imidazoles; monocarboxylic acid amide	antiprotozoal drug
4-methoxyamphetamine 4-methoxyamphetamine: para-methoxy derivative to amphetamine with hallucinogenic properties; minor descriptor (75-86); on line & INDEX MEDICUS search AMPHETAMINES (75-86); RN given refers to parent compound without isomeric designation	4.9	1	1
transferrin Transferrin: An iron-binding beta1-globulin that is synthesized in the LIVER and secreted into the blood. It plays a central role in the transport of IRON throughout the circulation. A variety of transferrin isoforms exist in humans, including some that are considered markers for specific disease states.	2.38	2	0
9,10-dihydro-9,10-dihydroxybenzo(a)pyrene 9,10-dihydro-9,10-dihydroxybenzo(a)pyrene: RN given refers to cpd without isomeric designation	3.68	10	0
alkenes [no description available]	2.42	2	0
glutamic acid Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.	3.08	4	0	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
glucaric acid Glucaric Acid: A sugar acid derived from D-glucose in which both the aldehydic carbon atom and the carbon atom bearing the primary hydroxyl group are oxidized to carboxylic acid groups.. D-glucaric acid : The D-enantiomer of glucaric acid.. glucaric acid : A hexaric acid derived by oxidation of sugar such as glucose with nitric acid.	2.69	3	0	glucaric acid	antineoplastic agent
azoxymethane Azoxymethane: A potent carcinogen and neurotoxic compound. It is particularly effective in inducing colon carcinomas.	2.9	1	0
sodium azide Sodium Azide: A cytochrome oxidase inhibitor which is a nitridizing agent and an inhibitor of terminal oxidation. (From Merck Index, 12th ed). sodium azide : The sodium salt of hydrogen azide (hydrazoic acid).	9.26	18	0	inorganic sodium salt	antibacterial agent; explosive; mitochondrial respiratory-chain inhibitor; mutagen
azides Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.	3.68	10	0	pseudohalide anion	mitochondrial respiratory-chain inhibitor
amoxicillin Amoxicillin: A broad-spectrum semisynthetic antibiotic similar to AMPICILLIN except that its resistance to gastric acid permits higher serum levels with oral administration.. amoxicillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-(4-hydroxyphenyl)acetamido group.	2.01	1	0	penicillin allergen; penicillin	antibacterial drug
n-methyl-7h-dibenzo(c,g)carbazole N-methyl-7H-dibenzo(c,g)carbazole: structure given in first source	1.99	1	0
tramadol Tramadol: A narcotic analgesic proposed for severe pain. It may be habituating.. tramadol : A racemate consisting of equal amounts of (R,R)- and (S,S)-tramadol. A centrally acting synthetic opioid analgesic, used (as the hydrochloride salt) to treat moderately severe pain. The (R,R)-enantiomer exhibits ten-fold higher analgesic potency than the (S,S)-enantiomer. Originally developed by Gruenenthal GmbH and launched in 1977, it was subsequently isolated from the root bark of the South African tree Nauclea latifolia.. (R,R)-tramadol : A 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol in which both stereocentres have R-configuration; the (R,R)-enantiomer of the racemic opioid analgesic tramadol, it exhibits ten-fold higher analgesic potency than the (S,S)-enantiomer.	4.9	1	1	2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol	adrenergic uptake inhibitor; antitussive; capsaicin receptor antagonist; delta-opioid receptor agonist; kappa-opioid receptor agonist; metabolite; mu-opioid receptor agonist; muscarinic antagonist; nicotinic antagonist; NMDA receptor antagonist; opioid analgesic; serotonergic antagonist; serotonin uptake inhibitor
cyclopenta(c,d)pyrene cyclopenta(c,d)pyrene: structure	3.47	8	0	pyrenes
vanadyl sulfate [no description available]	1.97	1	0	metal sulfate; vanadium coordination entity
gallium citrate [no description available]	4.9	1	1
4-acetylaminofluorene 4-acetylaminofluorene : A member of the class of acetamides that is acetamide in which one of the hydrogens attached to the nitrogen is replaced by a 9H-fluoren-4-yl group.	7.67	3	0	acetamides; fluorenes	mitogen
4,5-dihydroxy-4,5-dihydrobenzo(a)pyrene 4,5-dihydroxy-4,5-dihydrobenzo(a)pyrene: RN given refers to cpd without isomeric designation	3.92	13	0
1,2,3,4-tetrachlorodibenzofuran 1,2,3,4-tetrachlorodibenzofuran: structure in first source	2.03	1	0
7-ethoxycoumarin 7-ethoxycoumarin : A member of the class of coumarins that is umbelliferone in which the hydroxy group at position 7 is replaced by an ethoxy group.	4.11	16	0	aromatic ether; coumarins
acetylgalactosamine Acetylgalactosamine: The N-acetyl derivative of galactosamine.	1.96	1	0	N-acetyl-D-hexosamine; N-acetylgalactosamine	Escherichia coli metabolite; human metabolite; mouse metabolite
pcb 118 [no description available]	2.02	1	0	dichlorobenzene; pentachlorobiphenyl; trichlorobenzene
3,4,3',4'-tetrachlorobiphenyl 3,4,3',4'-tetrachlorobiphenyl: RN given refers to parent cpd. 3,3',4,4'-tetrachlorobiphenyl : A tetrachlorobiphenyl that is biphenyl in which the hydrogens at position 3 and 4 on each phenyl group are replaced by chlorines.	4.15	16	0	dichlorobenzene; tetrachlorobiphenyl
3,4,5,3',4',5'-hexachlorobiphenyl [no description available]	2.37	2	0	hexachlorobiphenyl; trichlorobenzene
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	4	2	0	aromatic ketone
paclitaxel Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).	3.29	6	0	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
2,3,4,5-tetrachlorobiphenyl tetrachlorobiphenyl : Any polychlorobiphenyl with molecular formula C12H6Cl4.	2.04	1	0	tetrachlorobenzene; tetrachlorobiphenyl
etoposide [no description available]	8.18	5	0	beta-D-glucoside; furonaphthodioxole; organic heterotetracyclic compound	antineoplastic agent; DNA synthesis inhibitor
1,2,7,8-tetrachlorodibenzo-p-dioxin 1,2,7,8-tetrachlorodibenzo-p-dioxin: structure in first source	2.05	1	0
2,5-dichlorobiphenyl 2,5-dichlorobiphenyl : A dichlorobiphenyl that is p-dichlorobenzene in which one of the hydrogens has been replaced by a phenyl group.	2.04	1	0	dichlorobenzene; dichlorobiphenyl
2,4'-dichlorobiphenyl 2,4'-dichlorobiphenyl: RN given refers to unlabeled cpd. 2,4'-dichlorobiphenyl : A dichlorobiphenyl that is chlorobenzene in which the hydrogen at position 2 has been replaced by a 4-chlorophenyl group.	2.04	1	0	dichlorobiphenyl; monochlorobenzenes
2,4,5,2',4',5'-hexachlorobiphenyl [no description available]	3.43	7	0	hexachlorobiphenyl
pcb 180 PCB 180: C12-H3-Cl7	2.48	2	0	polychlorobiphenyl
2,4,6-trichlorobiphenyl 2,4,6-trichlorobiphenyl: structure given in first source	2.04	1	0
2,5,2',5'-tetrachlorobiphenyl 2,2',5,5'-tetrachlorobiphenyl : A tetrachlorobiphenyl that is biphenyl in which the hydrogens at the 2 and 5 position of each benzene ring are replaced by chlorines.	2.94	4	0	dichlorobenzene; tetrachlorobiphenyl
1,2,3,4,6,7,8-heptachlorodibenzodioxin 1,2,3,4,6,7,8-heptachlorodibenzodioxin: contaminant of pentachlorophenol	1.97	1	0	polychlorinated dibenzodioxine
benzo(a)pyrene 7,8-oxide benzo(a)pyrene 7,8-oxide: RN given refers to cpd without isomeric designation; structure given in first source	2.66	3	0	pyrenes
lentinan [no description available]	7.25	1	0
6-hydroxychrysene chrysen-6-ol : A hydroxychrysene that is chrysene in which the hydrogen at position 6 has been replaced by a hydroxy group. It is a metabolite of the polycyclic aromatic hydrocarbon chrysene.	2	1	0	hydroxychrysene	xenobiotic metabolite
phorbol 12,13-dibutyrate Phorbol 12,13-Dibutyrate: A phorbol ester found in CROTON OIL which, in addition to being a potent skin tumor promoter, is also an effective activator of calcium-activated, phospholipid-dependent protein kinase (protein kinase C). Due to its activation of this enzyme, phorbol 12,13-dibutyrate profoundly affects many different biological systems.	1.97	1	0	butyrate ester; phorbol ester; tertiary alpha-hydroxy ketone
benzo(a)pyrene 4,5-epoxide benzo(a)pyrene 4,5-epoxide: RN given refers to cpd with unspecifiedisomeric designation	3.58	9	0	carbopolycyclic compound
1,2,3,7,8-pentachlorodibenzo-p-dioxin [no description available]	2.03	1	0	polychlorinated dibenzodioxine
1,6-dinitropyrene [no description available]	3.48	8	0	pyrenes
1,8-dinitropyrene [no description available]	2.68	3	0	pyrenes
vinclozolin vinclozolin : A racemate comprising equimolar amounts of (R)- and (S)-vinclozolin. A fungicide used mainly on oilseed rape, vines, fruit and vegetables to control Botrytis, Sclerotinia and Monilia spp.. 3-(3,5-dichlorophenyl)-5-ethenyl-5-methyl-2,4-oxazolidinedione : A member of the class of oxazolidinones that is 5-ethenyl-5-methyl-2,4-oxazolidinedione in which the imide hydrogen is replaced by a 3,5-dichlorophenyl group.	7.45	2	0	dicarboximide; dichlorobenzene; olefinic compound; oxazolidinone
2,3,7,8-tetrabromodibenzo-4-dioxin 2,3,7,8-tetrabromodibenzo-4-dioxin: structure given in first source. 2,3,7,8-tetrabromodibenzodioxine : An organobromine compound that is dibenzodioxine carrying four bromo substituents at positions 2, 3, 7 and 8.	1.95	1	0	dibenzodioxine; organobromine compound
ng-nitroarginine methyl ester NG-Nitroarginine Methyl Ester: A non-selective inhibitor of nitric oxide synthase. It has been used experimentally to induce hypertension.	2.03	1	0	alpha-amino acid ester; L-arginine derivative; methyl ester; N-nitro compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor
2,3,7,8-tetrachlorodibenzofuran 2,3,7,8-tetrachlorodibenzofuran: toxic product which was generated in Italy due to an explosion in a plant manufacturing 2,4,5-trichlorophenol	3.08	5	0	polychlorinated dibenzofuran
permethrin hemoglobin Atlanta-Coventry: Leu replaced by Pro at beta75 and Leu deleted at beta141	2.46	2	0	cyclopropanecarboxylate ester; cyclopropanes	agrochemical; ectoparasiticide; pyrethroid ester acaricide; pyrethroid ester insecticide; scabicide
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).	5.02	41	0
decamethrin decamethrin: pyrethroid insecticide; RN given refers to cpd without isomeric designation; structure	2	1	0	aromatic ether; cyclopropanecarboxylate ester; nitrile; organobromine compound	agrochemical; antifeedant; calcium channel agonist; EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; pyrethroid ester insecticide
7,8-dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide 7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide: 7,8,8a,9a-Tetrahydrobenzo(10,11)chryseno (3,4-b)oxirene-7,8-diol. A benzopyrene derivative with carcinogenic and mutagenic activity.	9.42	256	0	epoxide	intercalator
methyl(acetoxymethyl)nitrosamine methyl(acetoxymethyl)nitrosamine: RN given refers to parent cpd; structure in seventh source	2.39	2	0
2-hydroxybenzo(a)pyrene 2-hydroxybenzo(a)pyrene: RN given refers to parent cpd; structure in first source	1.97	1	0	ortho- and peri-fused polycyclic arene
2,3,4,7,8-pentachlorodibenzofuran 2,3,4,7,8-pentachlorodibenzofuran: structure given in first source	6.98	1	0	polychlorinated dibenzofuran
metalaxyl metalaxyl: RN given refers to (DL-Ala)-isomer. metalaxyl : A racemate comprising equal amounts of (R)- and (S)-metalaxyl. A systemic fungicide, it is active against phytopathogens of the order Peronosporales and is used to conrtrol Pythium in a number of vegetable crops.. methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate : An alanine derivative that is methyl alaninate in which one of the hydrogens attached to the nitrogen is substituted by a methoxyacetyl group, while the other is substituted by a 2,6-dimethylphenyl group.	1.98	1	0	alanine derivative; aromatic amide; carboxamide; ether; methyl ester
7,8,9,10-tetrahydroxytetrahydrobenzo(a)pyrene 7,8,9,10-tetrahydroxytetrahydrobenzo(a)pyrene: RN given refers to cpd without isomeric designation	2.89	4	0
6-nitrobenzo(a)pyrene [no description available]	3.47	8	0	ortho- and peri-fused polycyclic arene
6-amino-1,2-benzopyrone 6-amino-1,2-benzopyrone: selective inhibitor of adenosine diphosphoribosyl transferase; RN given refers to the parent compound	2	1	0
4-(n-methyl-n-nitrosamino)-1-(3-pyridyl)-1-butanone 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone: structure; from tobacco smoke	9.39	60	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.	3.51	8	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
colforsin Colforsin: Potent activator of the adenylate cyclase system and the biosynthesis of cyclic AMP. From the plant COLEUS FORSKOHLII. Has antihypertensive, positive inotropic, platelet aggregation inhibitory, and smooth muscle relaxant activities; also lowers intraocular pressure and promotes release of hormones from the pituitary gland.	1.96	1	0	acetate ester; cyclic ketone; labdane diterpenoid; organic heterotricyclic compound; tertiary alpha-hydroxy ketone; triol	adenylate cyclase agonist; anti-HIV agent; antihypertensive agent; plant metabolite; platelet aggregation inhibitor; protein kinase A agonist
glu-p-2 Glu-P-2: RN given refers to parent cpd	2.03	1	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	3.37	7	0	imidazopyridine
r 6597 2-nitronaphtho(2,1-b)furan: structure given in first source	1.97	1	0
1-nitrobenzo(a)pyrene [no description available]	3.38	7	0
3-nitrobenzo(a)pyrene [no description available]	3.38	7	0
fomesafen fomesafen: a protoporphyrinogen oxidase-inhibiting herbicide. fomesafen : An N-sulfonylcarboxamide that is N-(methylsulfonyl)benzamide in which the phenyl ring is substituted by a nitro group at position 2 and a 2-chloro-4-(trifluoromethyl)phenoxy group at position 5. A protoporphyrinogen oxidase inhibitor, it was specially developed for use (generally as the corresponding sodium salt, fomesafen-sodium) for post-emergence control of broad-leaf weeds in soya.	2.01	1	0	aromatic ether; C-nitro compound; monochlorobenzenes; N-sulfonylcarboxamide; organofluorine compound; phenols	agrochemical; EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor; herbicide
1,3-dinitropyrene [no description available]	1.97	1	0	pyrenes
2-nitro-8-methoxynaphtho(2,1-b)furan [no description available]	1.97	1	0
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.	4.35	20	0	imidazoquinoline	carcinogenic agent
3-chloro-4-(dichloromethyl)-5-hydroxy-2(5h)-furanone 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone: structure given in first source	2.92	4	0	butenolide
vufb 13468 VUFB 13468: structure given in first source	2	1	0
mifepristone Mifepristone: A progestational and glucocorticoid hormone antagonist. Its inhibition of progesterone induces bleeding during the luteal phase and in early pregnancy by releasing endogenous prostaglandins from the endometrium or decidua. As a glucocorticoid receptor antagonist, the drug has been used to treat hypercortisolism in patients with nonpituitary CUSHING SYNDROME.	2.47	2	0	3-oxo-Delta(4) steroid; acetylenic compound; tertiary amino compound	abortifacient; contraceptive drug; hormone antagonist; synthetic oral contraceptive
itraconazole Itraconazole: A triazole antifungal agent that inhibits cytochrome P-450-dependent enzymes required for ERGOSTEROL synthesis.. itraconazole : An N-arylpiperazine that is cis-ketoconazole in which the imidazol-1-yl group is replaced by a 1,2,4-triazol-1-yl group and in which the actyl group attached to the piperazine moiety is replaced by a p-[(+-)1-sec-butyl-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl]phenyl group. A potent P-glycoprotein and CYP3A4 inhibitor, it is used as an antifungal drug for the treatment of various fungal infections, including aspergillosis, blastomycosis, candidiasis, chromoblastomycosis, coccidioidomycosis, cryptococcosis, histoplasmosis, and sporotrichosis.	4.9	1	1	aromatic ether; conazole antifungal drug; cyclic ketal; dichlorobenzene; dioxolane; N-arylpiperazine; triazole antifungal drug; triazoles	EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor; Hedgehog signaling pathway inhibitor; P450 inhibitor
5,9-dimethyldibenzo(c,g)carbazole 5,9-dimethyldibenzo(c,g)carbazole: structure given in first source	2.42	2	0
antineoplaston a10 antineoplaston A10: peptide analogue isolated from human urine	6.97	1	0
1,2-dihydroxy-epoxy-1,2,3,4-tetrahydro-5-methylchrysene 1,2-dihydroxy-epoxy-1,2,3,4-tetrahydro-5-methylchrysene: 5-methyl group increases its carcinogenic activity	2.02	1	0
fadrozole Fadrozole: A selective aromatase inhibitor effective in the treatment of estrogen-dependent disease including breast cancer.	2.04	1	0	imidazopyridine
3,7-dinitrofluoranthene [no description available]	1.97	1	0	nitronaphthalene
zileuton [no description available]	2.45	2	0	1-benzothiophenes; ureas	anti-asthmatic drug; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; ferroptosis inhibitor; leukotriene antagonist; non-steroidal anti-inflammatory drug
atorvastatin [no description available]	7.76	2	0	aromatic amide; dihydroxy monocarboxylic acid; monofluorobenzenes; pyrroles; statin (synthetic)	environmental contaminant; xenobiotic
lamivudine [no description available]	4.9	1	1	monothioacetal; nucleoside analogue; oxacycle; primary alcohol	allergen; anti-HBV agent; antiviral drug; EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor; HIV-1 reverse transcriptase inhibitor; prodrug
emtricitabine Emtricitabine: A deoxycytidine analog and REVERSE TRANSCRIPTASE INHIBITOR with antiviral activity against HIV-1 and HEPATITIS B viruses. It is used to treat HIV INFECTIONS.. emtricitabine : An organofluorine compound that is 5-fluorocytosine substituted at the 1 position by a 2-(hydroxymethyl)-1,3-oxathiolan-5-yl group (2R,5S configuration). It is used in combination therapy for the treatment of HIV-1 infection.	4.9	1	1	monothioacetal; nucleoside analogue; organofluorine compound; pyrimidone	antiviral drug; HIV-1 reverse transcriptase inhibitor
octyl gallate [no description available]	2	1	0	gallate ester	food antioxidant; hypoglycemic agent; plant metabolite
allyl formate [no description available]	1.98	1	0
sodium molybdate(vi) sodium molybdate(VI): RN given refers to molybdic acid, di-Na salt. sodium molybdate (anhydrous) : An inorganic sodium salt having molybdate as the counterion.	1.96	1	0	inorganic sodium salt	poison
potassium superoxide [no description available]	1.98	1	0
florisil Florisil: hard, porous, granular substance used in vitamin analysis, chromatography, & antibiotic processing	1.97	1	0
dimethylhydrazines Dimethylhydrazines: Hydrazines substituted with two methyl groups in any position.	4.67	9	0
methylallyl trisulfide methylallyl trisulfide: platelet aggregation inhibitor in garlic	2.37	2	0
4-nitropyrene [no description available]	1.98	1	0	pyrenes
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	2.67	3	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	3.7	10	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.	6.29	11	1	aromatic amine; imidazoquinoxaline	carcinogenic agent; genotoxin; Maillard reaction product; mutagen
sudan iii sudan III: structure in first source. Sudan III : A bis(azo) compound that is 2-naphthol substituted at position 1 by a 4-{[(2-methylphenyl)diazenyl]phenyl}diazenyl group. A fat-soluble dye predominantly used for demonstrating triglycerides in frozen sections, but which may also stain some protein bound lipids in paraffin sections.	2.68	3	0	azobenzenes; bis(azo) compound; naphthols	carcinogenic agent; fluorochrome; histological dye
acridine orange Acridine Orange: A cationic cytochemical stain specific for cell nuclei, especially DNA. It is used as a supravital stain and in fluorescence cytochemistry. It may cause mutations in microorganisms.. acridine orange : Fluorescent dye useful for cell cycle determination. It is cell-permeable, and interacts with DNA and RNA by intercalation or electrostatic attractions respectively.. acridine orange free base : A member of the class of aminoacridines that is acridine carrying two dimethylamino substituents at positions 3 and 6. The hydrochloride salt is the fluorescent dye 'acridine orange', used for cell cycle determination.	2.39	2	0	aminoacridines; aromatic amine; tertiary amino compound	fluorochrome; histological dye
allyl methyl disulfide allyl methyl disulfide: structure given in first source. allyl methyl disulfide : An organic disulfide having allyl and methyl as the two organic groups.	1.97	1	0	organic disulfide	plant metabolite; volatile oil component
sodium persulfate sodium persulfate: RN given refers to peroxydisulfuric acid, di-Na salt	2.21	1	0
caloreen caloreen: glucose polymer with average length of five glucose units for dietary energy supplement. dextrin : Glucans produced by the hydrolysis of starch or glycogen. They are mixtures of polymers of D-glucose units linked by alpha(1->4) or alpha(1->6) glycosidic bonds.	1.97	1	0
3-nitroperylene 3-nitroperylene: RN given refers to cpd with nitro group in position 3	2.36	2	0	phenanthrenes
trazodone hydrochloride Triticum: A plant genus of the family POACEAE that is the source of EDIBLE GRAIN. A hybrid with rye (SECALE CEREALE) is called TRITICALE. The seed is ground into FLOUR and used to make BREAD, and is the source of WHEAT GERM AGGLUTININS.. trazodone hydrochloride : A hydrochloride salt prepared from equimolar amounts of trazodone and hydrogen chloride.	3.87	12	0	hydrochloride	adrenergic antagonist; antidepressant; H1-receptor antagonist; sedative; serotonin uptake inhibitor
3,4,5,3',4'-pentachlorobiphenyl 3,3',4,4',5-pentachlorobiphenyl : A pentachlorobiphenyl in which the chlorines are located at the 3, 4, 5, 3', and 4' positions.	4.07	14	0	pentachlorobiphenyl; trichlorobenzene
efavirenz efavirenz: HIV-1 reverse transcriptase inhibitor. efavirenz : 1,4-Dihydro-2H-3,1-benzoxazin-2-one substituted at the 4 position by cyclopropylethynyl and trifluoromethyl groups (S configuration) and at the 6 position by chlorine. A non-nucleoside reverse transcriptase inhibitor with activity against HIV, it is used with other antiretrovirals for combination therapy of HIV infection.	4.9	1	1	acetylenic compound; benzoxazine; cyclopropanes; organochlorine compound; organofluorine compound	antiviral drug; HIV-1 reverse transcriptase inhibitor
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.	3.43	7	0	D-glucopyranose	epitope; mouse metabolite
ursolic acid [no description available]	2.39	2	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	geroprotector; plant metabolite
norharman norharman: RN given refers to parent cpd. beta-carboline : The parent compound of the beta-carbolines, a tricyclic structure comprising an indole ring system ortho- fused to C-3 and C-4 of a pyridine ring.	1.97	1	0	beta-carbolines; mancude organic heterotricyclic parent	fungal metabolite; marine metabolite
thiazolyl blue thiazolyl blue: RN & II refers to bromide. 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide : The bromide salt of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium.	3.14	5	0	organic bromide salt	colorimetric reagent; dye
thymidine 5'-triphosphate thymidine 5'-triphosphate: RN given refers to parent cpd. dTTP : A thymidine phosphate having a triphosphate group at the 5'-position.	2.11	1	0	pyrimidine 2'-deoxyribonucleoside 5'-triphosphate; thymidine phosphate	Escherichia coli metabolite; mouse metabolite
baicalin [no description available]	2.08	1	0	dihydroxyflavone; glucosiduronic acid; glycosyloxyflavone; monosaccharide derivative	antiatherosclerotic agent; antibacterial agent; anticoronaviral agent; antineoplastic agent; antioxidant; cardioprotective agent; EC 2.7.7.48 (RNA-directed RNA polymerase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; ferroptosis inhibitor; neuroprotective agent; non-steroidal anti-inflammatory drug; plant metabolite; prodrug
5-methylcytosine 5-Methylcytosine: A methylated nucleotide base found in eukaryotic DNA. In ANIMALS, the DNA METHYLATION of CYTOSINE to form 5-methylcytosine is found primarily in the palindromic sequence CpG. In PLANTS, the methylated sequence is CpNpGp, where N can be any base.. 5-methylcytosine : A pyrimidine that is a derivative of cytosine, having a methyl group at the 5-position.	4.7	5	0	methylcytosine; pyrimidines	human metabolite
diacetylfluorescein [no description available]	2.03	1	0
epigallocatechin gallate epigallocatechin gallate: a steroid 5alpha-reductase inhibitor and antimutagen in green tea (Camellia sinensis). (-)-epigallocatechin 3-gallate : A gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (-)-epigallocatechin.	5.34	17	0	flavans; gallate ester; polyphenol	antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite
fluorexon fluorexon: structure	2	1	0	xanthene dye	fluorochrome
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.	2.73	3	0	gallocatechin	antioxidant; metabolite; radical scavenger
2'-deoxycytidine 5'-triphosphate 2'-deoxycytidine 5'-triphosphate: RN given refers to unlabeled parent cpd	2.11	1	0	2'-deoxycytidine phosphate; pyrimidine 2'-deoxyribonucleoside 5'-triphosphate	Escherichia coli metabolite; human metabolite; mouse metabolite
1,2-dipalmitoylphosphatidylglycerol dipalmitoyl phosphatidylglycerol : A phosphatidylglycerol in which the phosphatidyl acyl groups are both palmitoyl.	2.21	1	0	phosphatidylglycerol
5-bromo-4-chloro-3-indolyl beta-galactoside 5-bromo-4-chloro-3-indolyl beta-galactoside: enzyme substrate for beta-galactosidase. 5-bromo-4-chloro-3-indolyl beta-D-galactoside : An indolyl carbohydrate that is the beta-D-galactoside of 3-hydroxy-1H-indole in which the indole moiety is substituted at positions 4 and 5 by chlorine and bromine, respectively. It is used to test for the presence of an enzyme, beta-galactosidase, which cleaved the glycosidic bond to give 5-bromo-4-chloro-3-hydroxy-1H-indole, which immediately dimerises to give an intensely blue product.	1.99	1	0	beta-D-galactoside; D-aldohexose derivative; indolyl carbohydrate; organobromine compound; organochlorine compound	chromogenic compound
lissamine rhodamine b lissamine rhodamine B: RN given refers to parent cpd; Lissamine Rhodamine B refers to Na salt	2.5	2	0
1,2,3,4,6-pentakis-O-galloyl-beta-D-glucose pentagalloylglucose: pentahydroxy gallic acid ester of glucose; a phytogenic antineoplastic agent and antibacterial agent. 1,2,3,4,6-pentakis-O-galloyl-beta-D-glucose : A galloyl-beta-D-glucose compound having five galloyl groups in the 1-, 2-, 3-, 4- and 6-positions.	2.05	1	0	gallate ester; galloyl beta-D-glucose	anti-inflammatory agent; antineoplastic agent; geroprotector; hepatoprotective agent; plant metabolite; radiation protective agent; radical scavenger
tris(2,2'-bipyridine)ruthenium(II) tris(2,2'-bipyridyl)ruthenium(II): a fluorescent dye; structure in first source	2.02	1	0	ruthenium coordination entity	fluorochrome
fluorophosphate fluorophosphate: inhibits Phosphorylas phosphatase irreversibly; RN given refers to parent cpd	1.97	1	0	fluorine molecular entity; phosphoric acid derivative
o-(6)-methylguanine O-(6)-methylguanine: structure. 6-O-methylguanine : A methylguanine in which the methyl group is positioned on the oxygen at position 6. Formed in DNA by alkylation of the oxygen atom of guanine, most often by N-nitroso compounds and sometimes due to methylation by other compounds such as endogenous S-adenosylmethionine, it base-pairs to thymine rather than cytidine, causing a G:C to A:T transition in DNA.. methylguanine : A 2-aminopurine that is guanine bearing a single methyl substituent.	2.43	2	0	methylguanine	mutagen
peroxynitric acid [no description available]	2	1	0	nitrogen oxoacid
glutathione disulfide Glutathione Disulfide: A GLUTATHIONE dimer formed by a disulfide bond between the cysteine sulfhydryl side chains during the course of being oxidized.	2.9	4	0	glutathione derivative; organic disulfide	Escherichia coli metabolite; mouse metabolite
trenbolone acetate Trenbolone Acetate: An anabolic steroid used mainly as an anabolic agent in veterinary practice.	2.4	2	0	steroid ester
2-methoxyestradiol 2-methoxy-17beta-estradiol : A 17beta-hydroxy steroid, being 17beta-estradiol methoxylated at C-2.	2.07	1	0	17beta-hydroxy steroid; 3-hydroxy steroid	angiogenesis modulating agent; antimitotic; antineoplastic agent; human metabolite; metabolite; mouse metabolite
salicylhydroxamic acid [no description available]	2.02	1	0	hydroxamic acid; phenols	antibacterial drug; EC 1.11.2.2 (myeloperoxidase) inhibitor; EC 3.5.1.5 (urease) inhibitor; trypanocidal drug
1,7-phenanthroline [no description available]	2.69	3	0	phenanthroline
triazoles Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.	2.72	3	0	1,2,3-triazole
pinocembrin pinocembrin : A dihydroxyflavanone in which the two hydroxy groups are located at positions 5 and 7. A natural product found in Piper sarmentosum and Cryptocarya chartacea.	7.31	1	0	(2S)-flavan-4-one; dihydroxyflavanone	antineoplastic agent; antioxidant; metabolite; neuroprotective agent; vasodilator agent
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.	2.71	3	0	pentamethoxyflavone	antineoplastic agent; plant metabolite
isopimpinellin isopimpinellin: from Ruta graveolens & Heracleum lanatum; structure	2.4	2	0	psoralens
isoimperatorin isoimperatorin: tumor necrosis factor antagonist isolated from Glehniae root. isoimperatorin : A member of the class of psoralens that is psoralen substituted by a prenyloxy group at position 5. Isolated from Angelica dahurica and Angelica koreana, it acts as a acetylcholinesterase inhibitor.	1.99	1	0	psoralens	EC 3.1.1.7 (acetylcholinesterase) inhibitor; 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.	4.3	6	0	anthocyanidin chloride
1,2-dithiol-3-thione 1,2-dithiol-3-thione: has antioxidant activity; structure given in first source	2.4	2	0	1,2-dithiole
picrolonic acid picrolonic acid: common lab reagent for alkaloids, amino acids & calcium; found mutagenic for Salmonella typhimurium; structure	1.97	1	0
fluorodeoxyglucose f18 Fluorodeoxyglucose F18: The compound is given by intravenous injection to do POSITRON-EMISSION TOMOGRAPHY for the assessment of cerebral and myocardial glucose metabolism in various physiological or pathological states including stroke and myocardial ischemia. It is also employed for the detection of malignant tumors including those of the brain, liver, and thyroid gland. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1162)	4.9	1	1	2-deoxy-2-((18)F)fluoro-D-glucose; 2-deoxy-2-fluoro-aldehydo-D-glucose
resorufin [no description available]	8.26	6	0	phenoxazine
4(5)-phenylimidazole 4(5)-phenylimidazole: tautomeric cpd; cytochrome P450 14alpha-sterol demethylase, CYP51 antagonist	1.96	1	0
cyclopropylamine cyclopropylamine: RN given refers to parent cpd. cyclopropylamine : A primary aliphatic amine that consists of cyclopropane bearing a single amino substituent.	2.02	1	0	primary aliphatic amine	mouse metabolite
3-chloroperbenzoic acid 3-chloroperbenzoic acid: oxidizing agent	1.97	1	0	monochlorobenzenes; peroxy acid
2-hydroxychavicol 2-hydroxychavicol: antimutagen from betel leaf; structure given in first source	2.02	1	0
atipamezole [no description available]	2.43	2	0
tyloxapol tyloxapol: non-ionic detergent with surface-active properties; incompatible with metals; surfactant also used in inhalation therapy; N1 is from CA Vol 90 Form Index; N1 in Chemline is same as synonym 8. tyloxapol : A polymeric compound resulting from the reaction of 4-(1,1,3,3-tetramethylbutyl)phenol with formaldehyde to give a chain in which 6-8 molecules are linked together by CH2 groups ortho to the phenolic hydroxy groups, which have then undergone reaction with oxirane to give polyoxyethyleneoxy moieties, Ar(OCH2CH2)xOH, where x = 8-10. A nonionic liquic polymer, it inhibits lipoprotein lipase and hence clearance of triglyceride from the plasma, so is used to induce hyperlipidaemia in test animals. Also used as a surfactant to aid liquefaction and removal of mucus- and pus-containing bronchopulmonary secretions.	2.07	1	0
masoprocol Masoprocol: A potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. The compound also inhibits formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase to a lesser extent. It also serves as an antioxidant in fats and oils.. masoprocol : The meso-form of nordihydroguaiaretic acid. An antioxidant found in the creosote bush, Larrea divaricata, it is a potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. It also inhibits (though to a lesser extent) formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase.	2.38	2	0	nordihydroguaiaretic acid	antineoplastic agent; hypoglycemic agent; lipoxygenase inhibitor; metabolite
tocophersolan tocophersolan: RN given refers to parent cpd	2.31	1	0	tocol
hesperetin [no description available]	8.4	2	0	3'-hydroxyflavanones; 4'-methoxyflavanones; monomethoxyflavanone; trihydroxyflavanone	antineoplastic agent; antioxidant; plant metabolite
4-o-methyl-12-o-tetradecanoylphorbol 13-acetate [no description available]	1.97	1	0
magnolol [no description available]	2.73	3	0	biphenyls
nobiletin nobiletin : A methoxyflavone that is flavone substituted by methoxy groups at positions 5, 6, 7, 8, 3' and 4' respectively.	2.46	2	0	methoxyflavone	antineoplastic agent; plant metabolite
teleocidin b-4 teleocidins: structure; RN given refers to teleocidin	1.97	1	0
picropodophyllin picropodophyllin: isolated from American May apple (Podophyllum); inhibits IGF-I autophosphorylation without interfering with tyrosine kinase activity. picropodophyllotoxin : An organic heterotetracyclic compound that has a furonaphthodioxole skeleton bearing 3,4,5-trimethoxyphenyl and hydroxy substituents.	2.11	1	0	furonaphthodioxole; lignan; organic heterotetracyclic compound	antineoplastic agent; insulin-like growth factor receptor 1 antagonist; plant metabolite; tyrosine kinase inhibitor
5-diazouracil 5-diazouracil: RN given refers to parent cpd; structure	1.96	1	0
o(6)-methyl-2'-deoxyguanosine O(6)-methyl-2'-deoxyguanosine: RN given refers to (beta)-isomer. O(6)-methyl-2'-deoxyguanosine : A purine 2'-deoxyribonucleoside having O(6)-methylguanine as the nucleobase.	1.98	1	0	purine 2'-deoxyribonucleoside
prochloraz Mirage: a feldspathic porcelain that can be etched & bonded to the tooth. prochloraz : A member of the class of ureas that is 1H-imidazole-1-carboxamide substituted by a propyl and a 2-(2,4,6-trichlorophenoxy)ethyl group at the amino nitrogen atom. A fungicide active against a wide range of diseases affecting field crops, fruit, turf and vegetables.	1.97	1	0	amide fungicide; aromatic ether; conazole fungicide; imidazole fungicide; imidazoles; trichlorobenzene; ureas	antifungal agrochemical; EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor; environmental contaminant; xenobiotic
1,1,1-trifluoro-2,4-pentanedione 1,1,1-trifluoro-2,4-pentanedione: structure in first source	1.97	1	0
ceric oxide ceric oxide: RN given refers to cpd with MF CeO2. ceric oxide : A metal oxide with formula CeO2. It is used for polishing glass, in coatings for infra-red filters to prevent reflection, and as an oxidant and catalyst in organic synthesis.	2.82	2	0	cerium molecular entity; metal oxide
perfluorooctane sulfonic acid perfluorooctane-1-sulfonic acid : A perfluoroalkanesulfonic acid that is octane-1-sulfonic acid in which all seventeen of the hydrogens that are attached to carbons hvae been replaced by fluorines.	3.27	5	0	perfluoroalkanesulfonic acid	antilipemic drug; persistent organic pollutant
atovaquone Atovaquone: A hydroxynaphthoquinone that has antimicrobial activity and is being used in antimalarial protocols.. atovaquone : A naphthoquinone compound having a 4-(4-chlorophenyl)cyclohexyl group at the 2-position and a hydroxy substituent at the 3-position.	2.11	1	0	hydroxy-1,2-naphthoquinone
octadecyl palmitate octadecyl palmitate: found in psoriatic nail, but not in normal nails. stearyl palmitate : A palmitate ester resulting from the formal condensation of the carboxy group of palmitic acid with the hydroxy group of stearyl alcohol.	1.98	1	0	hexadecanoate ester; wax ester	coral metabolite; cosmetic
2,2-bis(4-hydroxyphenyl)-1,1,1-trichloroethane 2,2-bis(4-hydroxyphenyl)-1,1,1-trichloroethane: methoxychlor metabolite	2.04	1	0	bisphenol
9,9-bis(4-hydroxyphenyl)fluorene fluorene-9-bisphenol: derivative of bisphenol A	2.41	1	0	fluorenes; polyphenol	anti-estrogen
7-methylbenz(c)acridine [no description available]	2.88	4	0
1-pyrenebutyrate 1-pyrenebutyrate: fluorescent probe; RN given refers to 1-pyrenebutyrate	2.05	1	0
1-benzylimidazole 1-benzylimidazole: inhibits human thromboxane synthetase	1.97	1	0
erucin [no description available]	7.46	2	0	isothiocyanate
1-phenylimidazole 1-phenylimidazole: ligand for cytochrome P-450 & inhibitor of microsomal oxidation	1.97	1	0
methiin methiin: distributed in Liliaceae(garlic, onions, etc.) & Cruciferae (cabbage, radish, etc.); one of greater sources of sulfur-containing amino acids in Japan; studied for nutritional value; increased splenic iron decrease erythrocyte counts; RN given refers to cpd without isomeric designation	1.98	1	0	alpha-amino acid
n-hydroxymethylformamide N-hydroxymethylformamide: structure given in first source	1.99	1	0
eriocitrin eriocitrin: structure in first source. eriocitrin : A disaccharide derivative that consists of eriodictyol substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	7.25	1	0	3'-hydroxyflavanones; 4'-hydroxyflavanones; disaccharide derivative; flavanone glycoside; rutinoside; trihydroxyflavanone	antioxidant
acetaminophen sulfate ester acetaminophen sulfate ester: RN given refers to parent cpd; structure given in first source. paracetamol sulfate : An aryl sulfate that is paracetamol in which the hydroxy group has been replaced by a sulfooxy group.	1.97	1	0	acetamides; aryl sulfate	drug metabolite
acetaminophen glucuronide acetaminophen glucuronide: acetaminophen metabolite in rats. acetaminophen O-beta-D-glucosiduronic acid : A beta-D-glucosiduronic acid that is the O-glucuronide of paracetamol (acetaminophen).	2.38	2	0	beta-D-glucosiduronic acid	drug metabolite
clarithromycin Clarithromycin: A semisynthetic macrolide antibiotic derived from ERYTHROMYCIN that is active against a variety of microorganisms. It can inhibit PROTEIN SYNTHESIS in BACTERIA by reversibly binding to the 50S ribosomal subunits. This inhibits the translocation of aminoacyl transfer-RNA and prevents peptide chain elongation.. clarithromycin : The 6-O-methyl ether of erythromycin A, clarithromycin is a macrolide antibiotic used in the treatment of respiratory-tract, skin and soft-tissue infections. It is also used to eradicate Helicobacter pylori in the treatment of peptic ulcer disease. It prevents bacteria from growing by interfering with their protein synthesis.	2.01	1	0	macrolide antibiotic	antibacterial drug; environmental contaminant; protein synthesis inhibitor; xenobiotic
cyprodinil cyprodinil: structure in first source. cyprodinil : A member of the class of aminopyrimidine that is N-phenylpyrimidin-2-amine carrying additional cyclopropyl and methyl substituents at positions 4 and 6 respectively. A broad spectrum fungicide used to control a range of pathogens including Tapesia yallundae, Botrytis spp., Alternaria spp. and Rhynchospium secalis. Whilst it is a recognised irritant no serious human health concerns have been identified. It is moderately toxic to birds as well as most aquatic organisms and earthworms, but it is not considered toxic to honeybees.	2.08	1	0	aminopyrimidine; anilinopyrimidine fungicide; cyclopropanes; secondary amino compound	antifungal agrochemical; aryl hydrocarbon receptor agonist; environmental contaminant; xenobiotic
3,6-dinitrobenzopyrene [no description available]	3.63	9	0
coenzyme a [no description available]	6.96	1	0	adenosine 3',5'-bisphosphate	coenzyme; Escherichia coli metabolite; mouse metabolite
7-chlorobenz(a)anthracene 7-chlorobenz(a)anthracene: structure given in first source	1.98	1	0
gentiopicroside gentiopicroside: a secoiridoid in Gentiana with rearrangement to two pyran rings	2.05	1	0	glycoside
5,7-dimethoxyflavone chrysin 5,7-dimethyl ether : A dimethoxyflavone that is the 5,7-dimethyl ether derivative of chrysin.	2.72	3	0	dimethoxyflavone	plant metabolite
nicotine (S)-nicotine : A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has S-configuration. The naturally occurring and most active enantiomer of nicotine, isolated from Nicotiana tabacum.	8.23	35	1	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
nsc-172755 butocin: S-substituted analog of mercaptopurine which functions as a cytostatic agent; minor descriptor (75-85); on-line search 6-MERCAPTOPURINE/AA (75-84); Index Medicus search MERCAPTOPURINE/analogs (75-84)	2.06	1	0
7-bromomethylbenzanthracene [no description available]	3.06	1	0
goethite [no description available]	2.11	1	0
glycidamide glycidamide: metabolite of acrylamide; structure given in first source	2.17	1	0
9-hydroxyellipticine 9-hydroxyellipticine: RN given refers to parent cpd. 9-hydroxyellipticine : A organic heterotetracyclic compound that is ellipticine in which the hydrogen at position 9 has been replaced by a hydroxy group.	1.96	1	0	organic heterotetracyclic compound; organonitrogen heterocyclic compound	antineoplastic agent
bitertanol bitertanol: a triazole fungicide; structure given in first source. bitertanol : A diastereoisomeric mixture composed of the enantiomeric pair (1R,2S)- and (1S,2R)-bitertanol in a 4:1 ratio with the enantiomeric pair (1R,2R)- and (1S,2S)-bitertanol. A fungicide used to control a range of diseases including scab, powder mildew, rusts and blackspot. It is moderately toxic to most animal and insect species but is non-toxic to honeybees.. 1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol : A member of the class of triazoles that is 3,3-dimethyl-1-(1,2,4-triazol-1-yl)butane-1,2-diol substituted at position O-1 by a biphenyl-4-yl group.	2.03	1	0	aromatic ether; biphenyls; secondary alcohol; triazoles
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.	2.47	2	0	tocopherol; vitamin E	algal metabolite; food antioxidant; plant metabolite
annatto annatto: coloring matter from seeds of Bixa orellana L., Bixaceae; contains bixin and pigments that give carotene reactions; induces hyperglycemia	2.05	1	0
glycidyl nitrate glycidyl nitrate: a nitric oxide donor; structure in first source. peptidoglycan : A peptidoglycosaminoglycan formed by alternating residues of beta-(1->4)-linked N-acetylglucosamine and N-acetylmuramic acid {2-amino-3-O-[(S)-1-carboxyethyl]-2-deoxy-D-glucose} residues. Attached to the carboxy group of the muramic acid is a peptide chain of three to five amino acids.	2.53	2	0
cortisol 21-mesylate cortisol 21-mesylate: alkylating derivative of cortisol	1.96	1	0
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.	2.46	2	0
dehydroabietic acid dehydroabietic acid: major aquatic toxicant in effluent of pulp and paper mills. dehydroabietic acid : An abietane diterpenoid that is abieta-8,11,13-triene substituted at position 18 by a carboxy group.. dehydroabietate : A monocarboxylic acid anion that is the conjugate base of dehydroabietic acid, obtained by deprotonation of the carboxy group.	7.9	4	0	abietane diterpenoid; carbotricyclic compound; monocarboxylic acid	allergen; metabolite
glucuronic acid Glucuronic Acid: A sugar acid formed by the oxidation of the C-6 carbon of GLUCOSE. In addition to being a key intermediate metabolite of the uronic acid pathway, glucuronic acid also plays a role in the detoxification of certain drugs and toxins by conjugating with them to form GLUCURONIDES.. D-glucuronic acid : The D-enantiomer of glucuronic acid.. D-glucopyranuronic acid : A D-glucuronic acid in cyclic pyranose form.	2.91	4	0	D-glucuronic acid	algal metabolite
2,2',4,4'-tetrabromodiphenyl ether [no description available]	3.69	9	0	aromatic ether; organobromine compound
methyl methanethiosulfinate methyl methanethiosulfinate: structure in first source; a metabolite of S-methyl cysteine sulfoxide	1.98	1	0	sulfur oxoacid derivative
2,5-dihydroxypyridine pyridine-2,5-diol : A dihydroxypyridine that is pyridine substituted by hydroxy groups at positions 2 and 5.	4.9	1	1	dihydroxypyridine	mouse metabolite
9,10-dihydroxy-9,10-dihydrophenanthrene 9,10-dihydroxy-9,10-dihydrophenanthrene: RN given refers to cpd without isomeric designation; structure given in first source	1.96	1	0	dihydrophenanthrenediol
6-fluorobenzo(a)pyrene [no description available]	2.65	3	0
1-pyrenyloxirane 1-pyrenyloxirane: structure	1.97	1	0
sesamolin sesamolin: constituent of sesame oil; RN given refers to the (1S-(1alpha,3aalpha,4alpha,6aalpha)-isomer); inhibits proliferation of human lymphocytic leukemia cells in culture	2.15	1	0	benzodioxoles
cobalt Cobalt: A trace element that is a component of vitamin B12. It has the atomic symbol Co, atomic number 27, and atomic weight 58.93. It is used in nuclear weapons, alloys, and pigments. Deficiency in animals leads to anemia; its excess in humans can lead to erythrocytosis.. cobalt(1+) : A monovalent inorganic cation obtained from cobalt.. cobalt atom : A cobalt group element atom that has atomic number 27.	2.68	3	0	cobalt group element atom; metal allergen	micronutrient
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	4.34	4	1	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.	3.41	7	0	17beta-hydroxy steroid; 3-hydroxy steroid; organofluorine compound; sulfoxide	antineoplastic agent; estrogen antagonist; estrogen receptor antagonist
hydrogen sulfite [no description available]	2.58	2	0	sulfur oxoanion	human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
ici 164384 ICI 164384: structure given in first source. ICI-164384 : A 3-hydroxy steroid that is 17beta-estradiol substituted by a 11-[butyl(methyl)amino]-11-oxoundecyl group at position 7R. It is a steroidal antioestrogen that inhibits the cell proliferation of breast-carcinoma cell lines.	1.99	1	0	17beta-hydroxy steroid; 3-hydroxy steroid; tertiary carboxamide	anti-estrogen; antineoplastic agent; estrogen receptor antagonist
1-nitrosopyrene 1-nitrosopyrene: structure given in first source	1.97	1	0
vitamin b 6 Vitamin B 6: VITAMIN B 6 refers to several PICOLINES (especially PYRIDOXINE; PYRIDOXAL; & PYRIDOXAMINE) that are efficiently converted by the body to PYRIDOXAL PHOSPHATE which is a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, and aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into PYRIDOXAMINE phosphate. Although pyridoxine and Vitamin B 6 are still frequently used as synonyms, especially by medical researchers, this practice is erroneous and sometimes misleading (EE Snell; Ann NY Acad Sci, vol 585 pg 1, 1990). Most of vitamin B6 is eventually degraded to PYRIDOXIC ACID and excreted in the urine.	2.15	1	0
1,4-dihydropyridine [no description available]	2.06	1	0
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	1.97	1	0
4-(methylnitrosamino)-1-(3-pyridyl)-1-butan-1-ol 4-(methylnitrosamino)-1-(3-pyridyl)-1-butan-1-ol: structure in first source. 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol : A member of the class of nitrosamines that is butan-1-ol substituted by a pyridin-3-yl group at position 1 and by a methyl(nitroso)amino group at position 4. It is a major metabolite of nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), which is a carcinogen found in tobacco and responsible for inducing lung cancer in smokers.	2.75	3	0	nitrosamine; pyridines; secondary alcohol	biomarker; carcinogenic agent; human urinary metabolite
2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine: directly acting genotoxic metabolite of 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine. N-hydroxy-PhIP : An imidazopyridine that is 1H--imidazo[4,5-b]pyridine which is substituted at positions 1, 2, and 6 by methyl, hydoxyamino, and phenyl groups, respectively. The active metabolite of the dietary carcinogen PhIP.	2.4	2	0	hydroxylamine; imidazopyridine	carcinogenic agent; genotoxin; human xenobiotic metabolite; mouse metabolite; mutagen; neurotoxin; rat metabolite
1-hydroxymethylpyrene [no description available]	2.45	2	0
benz(j)aceanthrylene [no description available]	4.33	6	0	phenanthrenes
benzo(a)pyrene-7,8-dione benzo(a)pyrene-7,8-dione: a metabolite of benzo(a)pyrene; structure given in first source. benzo[a]pyrene-7,8-dione : An o-quinone resulting from the formal oxidation of both of the hydroxy groups of benzo[a]pyrene-cis-7,8-dihydrodiol. Benzo[a]pyrene-7,8-dione is a metabolite of the widespread carcinogen benzo[a]pyrene.	2.69	3	0	orthoquinones; pyrenes	genotoxin; xenobiotic metabolite
dihydrorhodamine 123 dihydrorhodamine 123: uncharged & nonfluorescent derivative of the laser dye rhodamine 123; flow cytometric indicator for respiratory burst activity in neutrophil granulocytes	2.02	1	0
benz(l)aceanthrylene benz(l)aceanthrylene: structure given in first source	2.67	3	0	phenanthrenes
pentoxyresorufin [no description available]	2.42	2	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.	3.55	8	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.	3.14	5	0	catechin; gallate ester; polyphenol	EC 3.2.1.1 (alpha-amylase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; metabolite
2-hydroxyethylvaline 2-hydroxyethylvaline: RN given refers to (DL)-isomer; RN for cpd without isomeric designation not available 11/88	1.98	1	0
deguelin deguelin: a natural product from Mundulea sericea; RN refers to (7aS-cis)-isomer; structure given in first source. deguelin : A rotenone that is 13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one substituted by methoxy groups at positions 9 and 10, and by two methyl groups at position 3 (the 7aS,13aS-stereoisomer). It exists in abundant quantities in the bark, roots, and leaves of the Leguminosae family of plants and reported to exert anti-tumour effects in various cancers.	7.71	3	0	aromatic ether; diether; organic heteropentacyclic compound; rotenones	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; antiviral agent; apoptosis inducer; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; mitochondrial NADH:ubiquinone reductase inhibitor; plant metabolite
propylisopropylacetamide propylisopropylacetamide: structure	2.65	3	0
parinaric acid parinaric acid: long-chain polyenoic fatty acid; RN given refers to cpd without isomeric designation. parinaric acid : An octadecatetraenoic acid containing a conjugated system of double bonds at positions 9, 11, 13 and 15.	6.98	1	0	octadecatetraenoic acid
cafestol [no description available]	3.51	2	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.	7.96	4	0
schizandrin b schizandrin B: a phytogenic antineoplastic agent with anti-inflammatory activity; isolated from Schisandra plant	2.13	1	0
bifendate 7,7'-dimethoxy-(4,4'-bi-1,3-benzodioxole)-5,5'-dicarboxylic acid dimethyl ester: structure given in first source	1.98	1	0
deoxyglucose Deoxyglucose: 2-Deoxy-D-arabino-hexose. An antimetabolite of glucose with antiviral activity.. deoxyglucose : A deoxyhexose comprising glucose having at least one hydroxy group replaced by hydrogen.	2	1	0
6-methyl-2-ethyl-3-hydroxypyridine 6-methyl-2-ethyl-3-hydroxypyridine: compound used in second source was chlorhydrate; has been used as retinoprotector	1.96	1	0
chrysene,2-diol-3,4-epoxide-1 chrysene,2-diol-3,4-epoxide-1: denotes tumorigenic activity; RN given refers to cpd without isomeric designation; structure	2.02	1	0
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	2.01	1	0
homoorientin homoorientin: isolated from Swertia japonica; structure given in first source	2.21	1	0	flavone C-glycoside; tetrahydroxyflavone	antineoplastic agent; radical scavenger
kahweol [no description available]	3.51	2	0	diterpenoid; furans; organic heteropentacyclic compound; primary alcohol; tertiary alcohol	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; antioxidant; apoptosis inducer; plant metabolite
trans-1,2-dihydro-1,2-naphthalenediol trans-1,2-dihydro-1,2-naphthalenediol: structure in first source. (1S,2S)-1,2-dihydronaphthalene-1,2-diol : The (1S,2S)-isomer of trans-1,2-dihydronaphthalene-1,2-diol.	3.05	4	0	trans-1,2-dihydronaphthalene-1,2-diol
6-methyl-1,3,8-trichlorodibenzofuran 6-methyl-1,3,8-trichlorodibenzofuran: structure given in first source	2.42	2	0
tanshinone tanshinone: from root of Salvia miltiorrhiza Bunge; RN given refers to tanshinone I; cardioprotective agent and neuroprotective agent	2.42	2	0	abietane diterpenoid	anticoronaviral agent
dibenzo(a,l)pyrene 11,12-dihydrodiol dibenzo(a,l)pyrene 11,12-dihydrodiol: structure given in first source	1.97	1	0
2-ethynylnaphthalene 2-ethynylnaphthalene: RN given refers to unlabeled parent cpd	2.67	3	0
monobutyryl cyclic amp monobutyryl cyclic AMP: RN given refers to parent cpd. N(6)-butyryl-cAMP : A 3',5'-cyclic purine nucleotide that is 3',5'-cyclic AMP in which the exocyclic amino group on the purine fragment is carrying a butyryl substituent.	1.96	1	0	3',5'-cyclic purine nucleotide; adenyl ribonucleotide; butanamides	protein kinase agonist
azidopyrene azidopyrene: hydrophobic, photolabile probe	1.96	1	0
benzoperylene benzoperylene: see also record for 1,12-benzperylene	2.38	2	0
benzo(a)pyrene-7,8,9,10-tetrol benzo(a)pyrene-7,8,9,10-tetrol: structure given in first source	3.6	9	0
7-methoxyresorufin [no description available]	2.01	1	0
caprylates Caprylates: Derivatives of caprylic acid. Included under this heading are a broad variety of acid forms, salts, esters, and amides that contain a carboxy terminated eight carbon aliphatic structure.. octanoate : A straight-chain saturated fatty acid anion that is the conjugate base of octanoic acid (caprylic acid); believed to block adipogenesis.	3.28	6	0	fatty acid anion 8:0; straight-chain saturated fatty acid anion	human metabolite; Saccharomyces cerevisiae metabolite
tris(2-carboxyethyl)phosphine tris(2-carboxyethyl)phosphine: water-soluble reagent which irreversibly reduces disulfides to thiols at room temperature & is active below neutral pH; used for quantitation of iodine and iodate. TCEP : A tertiary phosphine in which phosphane is substituted with three 2-carboxyethyl groups. It is a commonly used reducing agent.	4.9	1	1	phosphine derivative; tricarboxylic acid	reducing agent
coriandrin coriandrin: from Coriandrum sativum	2.4	2	0	isocoumarins
4-(acetoxymethylnitrosamino)-1-(3-pyridyl)-1-butanone 4-(acetoxymethylnitrosamino)-1-(3-pyridyl)-1-butanone: structure given in first source; a pyridyloxobutylating agent used for altering DNA	1.98	1	0
dibenzyl trisulfide dibenzyl trisulfide: structure in first source; an antiproliferative agent	2.31	1	0
peroxynitrous acid Peroxynitrous Acid: A potent oxidant synthesized by the cell during its normal metabolism. Peroxynitrite is formed from the reaction of two free radicals, NITRIC OXIDE and the superoxide anion (SUPEROXIDES).	2.73	3	0	nitrogen oxoacid
fullerene c60 Fullerenes: A polyhedral CARBON structure composed of around 60-80 carbon atoms in pentagon and hexagon configuration. They are named after Buckminster Fuller because of structural resemblance to geodesic domes. Fullerenes can be made in high temperature such as arc discharge in an inert atmosphere.. fullerene : A compound composed solely of an even number of carbon atoms, which form a cage-like fused-ring polycyclic system with twelve five-membered rings and the rest six-membered rings. The term has been broadened to include any closed cage structure consisting entirely of three-coordinate carbon atoms.	3.19	5	0	fullerene	geroprotector
gefitinib [no description available]	2.45	2	0	aromatic ether; monochlorobenzenes; monofluorobenzenes; morpholines; quinazolines; secondary amino compound; tertiary amino compound	antineoplastic agent; epidermal growth factor receptor antagonist
1-((3,5-dichloro)-2,6-dihydroxy-4-methoxyphenyl)-1-hexanone 1-((3,5-dichloro)-2,6-dihydroxy-4-methoxyphenyl)-1-hexanone: structure given in first source. 1-(3,5-dichloro-2,6-dihydroxy-4-methoxyphenyl)hexan-1-one : A differentiation-inducing factor that is hexaphenone bearing two chloro substituents at positions 3 and 5, two hydroxy substituents at positions 2 and 6 as well as a single methoxy substituent at position 4. A secreted, chlorinated molecule that controls cell fate during development of Dictyostelium cells.	2.03	1	0	dichlorobenzene; differentiation-inducing factor; monomethoxybenzene; resorcinols	eukaryotic metabolite; signalling molecule
phenyl-d-galactopyranoside phenyl-D-galactopyranoside: RN given refers to cpd without isomeric designation	1.99	1	0
tertiary-butyloxycarbonyl-valyl-prolyl-arginyl-7-amino-4-methylcoumarin tertiary-butyloxycarbonyl-valyl-prolyl-arginyl-7-amino-4-methylcoumarin: synthetic oligopeptide with fluorescent detector	1.97	1	0
psorospermin psorospermin: from Psorospermum febrifugum (Clusiaceae); some evidence it alkylates Gua N7 of DNA. psorospermin : An organic heterotetracyclic compound that is 1,2-dihydro-6H-furo[2,3-c]xanthene substituted by a hydroxy group at position 10, a methoxy group at position 5 nad a 2-methyloxiran-2-yl group at position 2.	2.03	1	0	epoxide; organic heterotetracyclic compound; xanthones	antineoplastic agent; plant metabolite
methotrexate [no description available]	2.4	2	0	dicarboxylic acid; monocarboxylic acid amide; pteridines	abortifacient; antimetabolite; antineoplastic agent; antirheumatic drug; dermatologic drug; DNA synthesis inhibitor; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; immunosuppressive agent
o-(glucuronic acid 2-sulfate)-(1--4)-o-(2,5)-anhydromannitol 6-sulfate O-(glucuronic acid 2-sulfate)-(1--4)-O-(2,5)-anhydromannitol 6-sulfate: disaccharide substrate derived from heparin	2.07	1	0
cysteine isopropyl ester cysteine isopropyl ester: a chemoprotectant against paracetamol-induced toxicity	1.98	1	0
delphinidin delphinidin: RN given refers to parent cpd;. delphinidin : An anthocyanidin cation consisting of benzopyrylium with hydroxy substituents at the 3-, 5- and 7-positions and a 3,4,5-trihydroxyphenyl group at the 2-position. It is a plant pigment responsible for the colours of the plants of the genera Viola and Delphinium.	2.03	1	0	5-hydroxyanthocyanidin	antineoplastic agent; biological pigment; plant metabolite
7-ethoxy-4-trifluoromethylcoumarin [no description available]	1.99	1	0
4b,5,9b,10-tetrahydroindeno(1,2-b)indole 4b,5,9b,10-tetrahydroindeno(1,2-b)indole: RN refers to (cis)-isomer; structure given in first source	3.37	1	1
carbapenems [no description available]	4.9	1	1
beta-lactams 2-azetidinone: structure in first source. azetidin-2-one : An unsubstituted beta-lactam compound.. beta-lactam : A lactam in which the amide bond is contained within a four-membered ring, which includes the amide nitrogen and the carbonyl carbon.	4.9	1	1	beta-lactam antibiotic allergen; beta-lactam
phytol [no description available]	7.21	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.	5.37	3	1	amino acid zwitterion; glutamine family amino acid; L-alpha-amino acid; proline; proteinogenic amino acid	algal metabolite; compatible osmolytes; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
cucurbitaceae Cucurbitaceae: The gourd plant family of the order Violales, subclass Dilleniidae, class Magnoliopsida. It is sometimes placed in its own order, Cucurbitales. 'Melon' generally refers to CUCUMIS; CITRULLUS; or MOMORDICA.	7.6	1	0
yh 439 YH 439: structure given in first source	2.72	3	0	aromatic amide; isopropyl ester; secondary carboxamide
cariporide cariporide: a selective sodium-hydrogen exchange subtype 1 inhibitor; structure in first source	2.42	2	0
1-ethynylpyrene 1-ethynylpyrene: RN & structure given in first source; RN not in Chemline 12/84	2.89	4	0
phorbols Phorbols: The parent alcohol of the tumor promoting compounds from CROTON OIL (Croton tiglium).	3.67	10	0	diterpene; terpenoid fundamental parent
kolaviron kolaviron: antihepatotoxic fraction of biflavonones from Garcinia kola seeds; phalloidine antagonist. kolaflavanone : A biflavonoid isolated from the seeds of Garcinia kola that has been shown to exhibit hepatoprotective activity.	2.11	1	0	4'-methoxyflavanones; biflavonoid; dihydroflavonols; ring assembly; secondary alpha-hydroxy ketone	hepatoprotective agent; plant metabolite
hydroxyl radical Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.	5.65	5	1	oxygen hydride; oxygen radical; reactive oxygen species
gallium oxide gallium oxide: RN given refers to unlabeled cpd	6.96	1	0
tipifarnib [no description available]	2.01	1	0	imidazoles; monochlorobenzenes; primary amino compound; quinolone	antineoplastic agent; apoptosis inducer; EC 2.5.1.58 (protein farnesyltransferase) inhibitor
titanium phosphate titanium phosphate: RN given refers to unspecified titanium phosphate	2.02	1	0
singlet oxygen Singlet Oxygen: An excited state of molecular oxygen generated photochemically or chemically. Singlet oxygen reacts with a variety of biological molecules such as NUCLEIC ACIDS; PROTEINS; and LIPIDS; causing oxidative damages.	11.29	11	1	chalcogen; monoatomic oxygen; nonmetal atom	macronutrient
carcinolipin carcinolipin: structure	1.97	1	0
peroxymonosulfate peroxymonosulfate: oxidizing agent in prevention of tooth discoloration; RN given refers to ion(2-)	4.9	1	1	sulfur oxide; sulfur oxoanion
aloesin aloesin: UP780 is a preparation of aloesin and an aloe polysaccharide that improves insulin sensitivity; human intestinal bacteria cleaves the C-glucosyl bond; structure given in first source	2.02	1	0	chromones
fenton's reagent Fenton's reagent: used for oxidizing sugars & alcohols	3.12	5	0
7,8-dihydroxy-9,10-epoxy-8-methyl-7,8,9,10-tetrahydrobenzo(a)pyrene 7,8-dihydroxy-9,10-epoxy-8-methyl-7,8,9,10-tetrahydrobenzo(a)pyrene: putative oxidized metabolite of 8-methylbenzo(a)pyrene; structure given in first source	2.39	2	0
zirconium phosphate zirconium phosphate: reagent for carcinoembryonic antigen determination in plasma from patients having benign or malignant disease; RN given refers to cpd with unspecified ratio	2.02	1	0
neodymium pyrocatechin disulfonate neodymium pyrocatechin disulfonate: rare earth metal complex	1.97	1	0
ampelopsin ampelopsin: hepatoprotective agent; isolated from Hovenia dulcis; RN given for (2R-trans)-isomer; structure in first source. (+)-dihydromyricetin : An optically active form of dihydromyricetin having (2R,3R)-configuration.	2.1	1	0	dihydromyricetin; secondary alpha-hydroxy ketone	antineoplastic agent; antioxidant; metabolite
calcium pyrophosphate [no description available]	1.98	1	0
boswellic acid boswellic acid: ursane type; RN given refers to (3alpha,4beta)-isomer; active principle of salai guggal; see also record for salai guggal	7.15	1	0	triterpenoid
biotin vitamin B7 : Any member of a group of vitamers that belong to the chemical structural class called biotins that exhibit biological activity against vitamin B7 deficiency. Vitamin B7 deficiency is very rare in individuals who take a normal balanced diet. Foods rich in biotin are egg yolk, liver, cereals, vegetables (spinach, mushrooms) and rice. Symptoms associated with vitamin B7 deficiency include thinning hair, scaly skin rashes around eyes, nose and mouth, and brittle nails. The vitamers include biotin and its ionized and salt forms.	4.92	6	0	biotins; vitamin B7	coenzyme; cofactor; Escherichia coli metabolite; fundamental metabolite; human metabolite; mouse metabolite; nutraceutical; prosthetic group; Saccharomyces cerevisiae metabolite
angiotensin ii Giapreza: injectable form of angiotensin II used to increase blood pressure in adult patients with septic or other distributive shock. Ile(5)-angiotensin II : An angiotensin II that acts on the central nervous system (PDB entry: 1N9V).	3	4	0	amino acid zwitterion; angiotensin II	human 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.	8.4	7	0
sb 203580 [no description available]	2.48	2	0	imidazoles; monofluorobenzenes; pyridines; sulfoxide	EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector; Hsp90 inhibitor; neuroprotective agent
limonin [no description available]	7.42	2	0	epoxide; furans; hexacyclic triterpenoid; lactone; limonoid; organic heterohexacyclic compound	inhibitor; metabolite; volatile oil component
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.	8.9	118	0	aflatoxin; aromatic ether; aromatic ketone	carcinogenic agent; human metabolite
troleandomycin Troleandomycin: A macrolide antibiotic that is similar to ERYTHROMYCIN.. troleandomycin : A semi-synthetic macrolide antibiotic obtained by acetylation of the three free hydroxy groups of oleandomycin. Troleandomycin is only found in individuals that have taken the drug.	1.97	1	0	acetate ester; epoxide; macrolide antibiotic; monosaccharide derivative; polyketide; semisynthetic derivative	EC 1.14.13.97 (taurochenodeoxycholate 6alpha-hydroxylase) inhibitor; xenobiotic
demecolcine Demecolcine: An alkaloid isolated from Colchicum autumnale L. and used as an antineoplastic.. (-)-demecolcine : A secondary amino compound that is (S)-colchicine in which the N-acetyl group is replaced by an N-methyl group. Isolable from the autumn crocus, Colchicum autumnale, it is less toxic than colchicine and is used as an antineoplastic.	3.76	3	0	alkaloid; secondary amino compound	antineoplastic agent; microtubule-destabilising agent
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.	2.39	2	0	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human blood serum metabolite
cortisone [no description available]	1.96	1	0	11-oxo steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	human metabolite; mouse 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.	2.77	3	0	2-nitrophenols; C-nitro compound; nitrotyrosine; non-proteinogenic alpha-amino acid
allylestrenol Allylestrenol: A synthetic steroid with progestational activity.	2.39	2	0	steroid
lanosterol [no description available]	2.35	2	0	14alpha-methyl steroid; 3beta-sterol; tetracyclic triterpenoid	bacterial metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
2-hydroxyestradiol 2-hydroxyestradiol: catechol estrogen; RN given refers to (17 beta)-isomer. 2-hydroxy-17beta-estradiol : A 2-hydroxy steroid that consists of 17beta-estradiol having an additional hydroxy group at position 2.	2.03	1	0	17beta-hydroxy steroid; 2-hydroxy steroid	carcinogenic agent; human metabolite; metabolite; mouse metabolite; prodrug
2-chlorobiphenyl 2-chlorobiphenyl: RN from Toxlit. 2-chlorobiphenyl : A monochlorobiphenyl carrying a single chloro substituent at position 2.. monochlorobiphenyl : A chlorobiphenyl carrying a single chloro substituent at unspecified position.. chlorobiphenyl : A chloroarene that consists of a biphenyl skeleton substituted by one or more chloro groups.	2.04	1	0	monochlorobiphenyl
anisomycin Anisomycin: An antibiotic isolated from various Streptomyces species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system.. (-)-anisomycin : An antibiotic isolated from various Streptomyces species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system.	2.03	1	0	monohydroxypyrrolidine; organonitrogen heterocyclic antibiotic	anticoronaviral agent; antimicrobial agent; antineoplastic agent; antiparasitic agent; bacterial metabolite; DNA synthesis inhibitor; protein synthesis inhibitor
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	7.2	17	1
potassium bromide potassium bromide : A metal bromide salt with a K(+) counterion.	2.05	1	0	potassium salt
lupeol [no description available]	2.48	2	0	pentacyclic triterpenoid; secondary alcohol	anti-inflammatory drug; plant metabolite
tricaine tricaine: request from searcher; RN given refers to parent cpd. tricaine : A benzoate ester that is the ethyl ester of 3-aminobenzoic acid. Used (in the form of its methanesulfonate salt) as an anaesthetic for fish.. tricaine methanesulfonate : A methanesulfonate salt obtained by reaction of tricaine with one molar equivalent of methanesulfonic acid. Used as an anaesthetic for fish.	6.96	1	0	methanesulfonate salt	general anaesthetic
acivicin [no description available]	2.13	1	0	isoxazoles; non-proteinogenic L-alpha-amino acid; organochlorine compound	antileishmanial agent; antimetabolite; antimicrobial agent; antineoplastic agent; EC 2.3.2.2 (gamma-glutamyltransferase) inhibitor; glutamine antagonist; metabolite
wortmannin [no description available]	2.06	1	0	acetate ester; cyclic ketone; delta-lactone; organic heteropentacyclic compound	anticoronaviral agent; antineoplastic agent; autophagy inhibitor; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor; geroprotector; Penicillium metabolite; radiosensitizing agent
acronine Acronine: A pyrano-acridone alkaloid found in RUTACEAE plants.. acronycine : An alkaloid antineoplastic agent isolated from Acronychia baueri.	2.03	1	0	acridone derivatives; alkaloid	antineoplastic agent; metabolite
5-demethylnobiletin 5-demethylnobiletin: antineoplastic from Citrus plants; structure in first source	2.82	2	0	ether; flavonoids
colupulone colupulone: structure given in first source; an antibiotic hops component; induces hepatic cytochrome P-4503A in the mouse. colupulone : A beta-bitter acid in which the acyl group is specified as isobutanoyl.	1.98	1	0	beta-bitter acid
dihydropyridines Dihydropyridines: Pyridine moieties which are partially saturated by the addition of two hydrogen atoms in any position.	2.06	1	0
methylmercuric chloride methylmercuric chloride: RN given refers to unlabeled cpd	2	1	0	chlorine molecular entity; mercury coordination entity; one-carbon compound
leupeptins Leupeptins: A group of acylated oligopeptides produced by Actinomycetes that function as protease inhibitors. They have been known to inhibit to varying degrees trypsin, plasmin, KALLIKREINS, papain and the cathepsins.	2.03	1	0
carboplatin [no description available]	2.52	2	0
glycogen glycogen : A polydisperse, highly branched glucan composed of chains of D-glucopyranose residues in alpha(1->4) glycosidic linkage, joined together by alpha(1->6) glycosidic linkages. A small number of alpha(1->3) glycosidic linkages and some cumulative alpha(1->6) links also may occur. The branches in glycogen typically contain 8 to 12 glucose residues.	2.49	2	0
n-acetylneuraminic acid N-Acetylneuraminic Acid: An N-acyl derivative of neuraminic acid. N-acetylneuraminic acid occurs in many polysaccharides, glycoproteins, and glycolipids in animals and bacteria. (From Dorland, 28th ed, p1518). N-acetylneuraminic acid : An N-acylneuraminic acid where the N-acyl group is specified as acetyl.	2.03	1	0	N-acetylneuraminic acids	antioxidant; bacterial metabolite; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor; human metabolite; mouse metabolite
mannose-6-phosphate beta-D-mannose 6-phosphate : A D-mannopyranose 6-phosphate with a beta-configuration at the anomeric position.	1.97	1	0	D-mannopyranose 6-phosphate
bradykinin [no description available]	1.97	1	0	oligopeptide	human blood serum metabolite; vasodilator agent
mevalonic acid Mevalonic Acid: A dihydroxy monocarboxylic acid and precursor in the biosynthetic pathway known as the mevalonate pathway, which produces terpenes and steroids that are vital for diverse cellular functions.. mevalonic acid : A racemate composed of equimolar amounts of (R)- and (S)-mevalonic acid.. (R)-mevalonic acid : The (R)-enantiomer of mevalonic acid.	2.05	1	0	3,5-dihydroxy-3-methylpentanoic acid
naringenin (S)-naringenin : The (S)-enantiomer of naringenin.	2.15	1	0	(2S)-flavan-4-one; naringenin	expectorant; plant metabolite
epiglucan epiglucan: a highly side-chain/branched alkali-insoluble cell wall glucan from fungus such as Epicoccum nigrum, Botrytis cinerea, ascomycetes & basidiomycetes; also isolated S-4001 from Lei Wan (polyporus mylitiae), HA-beta-glucan from mushroom Pleutotus ostreatus (Fr.) Quel., and translam from seaweed Laminaria cichorioides; with commercially important functional properties including emulsification and friction reduction.	2.75	3	0
oxytocin Oxytocin: A nonapeptide hormone released from the neurohypophysis (PITUITARY GLAND, POSTERIOR). It differs from VASOPRESSIN by two amino acids at residues 3 and 8. Oxytocin acts on SMOOTH MUSCLE CELLS, such as causing UTERINE CONTRACTIONS and MILK EJECTION.. oxytocin : A cyclic nonapeptide hormone with amino acid sequence CYIQNCPLG that also acts as a neurotransmitter in the brain; the principal uterine-contracting and milk-ejecting hormone of the posterior pituitary. Together with the neuropeptide vasopressin, it is believed to influence social cognition and behaviour.	2.42	2	0	heterodetic cyclic peptide; peptide hormone	oxytocic; vasodilator agent
7-dehydrocholesterol [no description available]	2.04	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; cholestanoid; Delta(5),Delta(7)-sterol	human metabolite; mouse metabolite
inositol 1,4,5-trisphosphate Inositol 1,4,5-Trisphosphate: Intracellular messenger formed by the action of phospholipase C on phosphatidylinositol 4,5-bisphosphate, which is one of the phospholipids that make up the cell membrane. Inositol 1,4,5-trisphosphate is released into the cytoplasm where it releases calcium ions from internal stores within the cell's endoplasmic reticulum. These calcium ions stimulate the activity of B kinase or calmodulin.	7.07	1	0	myo-inositol trisphosphate	mouse metabolite
ouabain Ouabain: A cardioactive glycoside consisting of rhamnose and ouabagenin, obtained from the seeds of Strophanthus gratus and other plants of the Apocynaceae; used like DIGITALIS. It is commonly used in cell biological studies as an inhibitor of the NA(+)-K(+)-EXCHANGING ATPASE.. cardiac glycoside : Steroid lactones containing sugar residues that act on the contractile force of the cardiac muscles.. ouabain : A steroid hormone that is a multi-hydroxylated alpha-L-rhamnosyl cardenoloide. It binds to and inhibits the plasma membrane Na(+)/K(+)-ATPase (sodium pump). It has been isolated naturally from Strophanthus gratus.	4.16	5	0	11alpha-hydroxy steroid; 14beta-hydroxy steroid; 5beta-hydroxy steroid; alpha-L-rhamnoside; cardenolide glycoside; steroid hormone	anti-arrhythmia drug; cardiotonic drug; EC 2.3.3.1 [citrate (Si)-synthase] inhibitor; EC 3.1.3.41 (4-nitrophenylphosphatase) inhibitor; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; ion transport inhibitor; plant metabolite
casein hydrolysate casein hydrolysate: an ingredient of trypticase soy broth; casitone is a tryptic digest of casein	2.02	1	0
puromycin [no description available]	3.06	1	0	puromycins	antiinfective agent; antimicrobial agent; antineoplastic agent; EC 3.4.11.14 (cytosol alanyl aminopeptidase) inhibitor; EC 3.4.14.2 (dipeptidyl-peptidase II) inhibitor; nucleoside antibiotic; protein synthesis inhibitor
adenosine 5'-o-(3-thiotriphosphate) adenosine 5'-O-(3-thiotriphosphate): RN given refers to cpd with unspecified locant for thio group; see also records for 1-thio & 2-thio-isomers. adenosine 5'-[gamma-thio]triphosphate : A nucleoside triphosphate analogue that is ATP in which one of the oxygens attached to 3-phosphate group is replaced by sulfur.	1.97	1	0	nucleoside triphosphate analogue
griseofulvin Griseofulvin: An antifungal agent used in the treatment of TINEA infections.. griseofulvin : An oxaspiro compound produced by Penicillium griseofulvum. It is used by mouth as an antifungal drug for infections involving the scalp, hair, nails and skin that do not respond to topical treatment.	2	1	0	1-benzofurans; antibiotic antifungal drug; benzofuran antifungal drug; organochlorine compound; oxaspiro compound	antibacterial agent; Penicillium metabolite
digitoxin Digitoxin: A cardiac glycoside sometimes used in place of DIGOXIN. It has a longer half-life than digoxin; toxic effects, which are similar to those of digoxin, are longer lasting. (From Martindale, The Extra Pharmacopoeia, 30th ed, p665). digitoxin : A cardenolide glycoside in which the 3beta-hydroxy group of digitoxigenin carries a 2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl trisaccharide chain.	3.48	2	0	cardenolide glycoside	EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor
phalloidine Phalloidine: Very toxic polypeptide isolated mainly from AMANITA phalloides (Agaricaceae) or death cup; causes fatal liver, kidney and CNS damage in mushroom poisoning; used in the study of liver damage.. phalloidin : A homodetic bicyclic heptapeptide having a sulfide bridge.	2.01	1	0	homodetic cyclic peptide
carnosol carnosol: isolated from Lepechinia hastata	2.42	2	0	diterpenoid
phorbol phorbol: RN given refers to (1aR-(1a alpha,1b beta,4a beta,7a alpha,7b alpha,8 alpha,9 beta,9b beta))-isomer; synonym isophorbol refers to (4a alpha)-isomer; structure in Merck Index, 9th ed, #7143. phorbol : A diterpenoid with the structure of tigliane hydroxylated at C-4, -9, -12(beta), -13 and -20, with an oxo group at C-3 and unsaturation at the 1- and 6-positions.	2.39	2	0	cyclic ketone; enone; tertiary alcohol; tertiary alpha-hydroxy ketone; tetracyclic diterpenoid
naringin [no description available]	1.99	1	0	(2S)-flavan-4-one; 4'-hydroxyflavanones; dihydroxyflavanone; disaccharide derivative; neohesperidoside	anti-inflammatory agent; antineoplastic agent; metabolite
ochratoxin a ochratoxin A: structure in first source & in Merck, 9th ed, #6549. ochratoxin A : A phenylalanine derivative resulting from the formal condensation of the amino group of L-phenylalanine with the carboxy group of (3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carboxylic acid (ochratoxin alpha). It is among the most widely occurring food-contaminating mycotoxins, produced by Aspergillus ochraceus, Aspergillus carbonarius and Penicillium verrucosum.	2.1	1	0	isochromanes; monocarboxylic acid amide; N-acyl-L-phenylalanine; organochlorine compound; phenylalanine derivative	Aspergillus metabolite; calcium channel blocker; carcinogenic agent; mycotoxin; nephrotoxin; Penicillium metabolite; teratogenic agent
jacobine jacobine: RN given refers to (15alpha,20S)-isomer; structure	1.96	1	0	pyrrolizine alkaloid
gingerol gingerol: an active ingredient in GINGER along with SHOGAOL. a nonvolatile methoxy phenyl decanone. gingerol : A beta-hydroxy ketone that is 5-hydroxydecan-3-one substituted by a 4-hydroxy-3-methoxyphenyl moiety at position 1; believed to inhibit adipogenesis. It is a constituent of fresh ginger.	3.06	4	0	beta-hydroxy ketone; guaiacols	antineoplastic agent; plant metabolite
lignans Lignans: A class of dibenzylbutane derivatives which occurs in higher plants and in fluids (bile, serum, urine, etc.) in man and other animals. These compounds, which have a potential anti-cancer role, can be synthesized in vitro by human fecal flora. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)	3.16	5	0
sodium arsenite sodium arsenite : An inoganic sodium salt with formula with formula NaAsO2.	4.32	7	0	arsenic molecular entity; inorganic sodium salt	antibacterial agent; antifungal agent; antineoplastic agent; carcinogenic agent; herbicide; insecticide; rodenticide
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	4.66	10	0	cyclodextrin
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.	2.03	1	0	acyl-CoA	acyl donor; coenzyme; effector; fundamental metabolite
ergosterol [no description available]	2.03	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; ergostanoid; phytosterols	fungal metabolite; Saccharomyces cerevisiae metabolite
trichostatin a trichostatin A: chelates zinc ion in the active site of histone deacetylases, resulting in preventing histone unpacking so DNA is less available for transcription; do not confuse with TRICHOSANTHIN which is a protein; found in STREPTOMYCES	2.45	2	0	antibiotic antifungal agent; hydroxamic acid; trichostatin	bacterial metabolite; EC 3.5.1.98 (histone deacetylase) inhibitor; geroprotector
tretinoin Tretinoin: An important regulator of GENE EXPRESSION during growth and development, and in NEOPLASMS. Tretinoin, also known as retinoic acid and derived from maternal VITAMIN A, is essential for normal GROWTH; and EMBRYONIC DEVELOPMENT. An excess of tretinoin can be teratogenic. It is used in the treatment of PSORIASIS; ACNE VULGARIS; and several other SKIN DISEASES. It has also been approved for use in promyelocytic leukemia (LEUKEMIA, PROMYELOCYTIC, ACUTE).. retinoic acid : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraenoic acid substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).. all-trans-retinoic acid : A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry.	4.73	30	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.	10.23	16	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
alpha-cyclodextrin alpha-cyclodextrin : A cycloamylose composed of six alpha-(1->4) linked D-glucopyranose units.	6.98	1	0	cyclodextrin
farnesol Farnesol: A colorless liquid extracted from oils of plants such as citronella, neroli, cyclamen, and tuberose. It is an intermediate step in the biological synthesis of cholesterol from mevalonic acid in vertebrates. It has a delicate odor and is used in perfumery. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). (2-trans,6-trans)-farnesol : The (2-trans,6-trans)-stereoisomer of farnesol.. farnesol : A farnesane sesquiterpenoid that is dodeca-2,6,10-triene substituted by methyl groups at positions 3, 7 and 11 and a hydroxy group at position 1.	2.46	2	0	farnesol	plant metabolite
resveratrol trans-resveratrol : A resveratrol in which the double bond has E configuration.	4.81	30	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).	6.05	38	0	retinol; vitamin A	human metabolite; mouse metabolite; plant metabolite
1,2-dilauroylphosphatidylcholine 1,2-dilauroylphosphatidylcholine: RN given refers to cpd without isomeric designation. 1,2-dilauroyl-sn-glycero-3-phosphocholine(1+) : A A 1,2-diacyl-sn-glycero-3-phosphocholine(1+) that is the dilauroyl diester of phosphatidiylcholine.	2.37	2	0	1,2-diacyl-sn-glycero-3-phosphocholine(1+)
cyanoginosin lr cyanoginosin LR: cyclic heptapeptide from cyanobacterium Microcystis aeruginosa. microcystin-LR : A microcystin consisting of D-alanyl, L-leucyl, (3S)-3-methyl-D-beta-aspartyl,L-arginyl, 2S,3S,4E,6E,8S,9S)-3-amino-4,5,6,7-tetradehydro-9-methoxy-2,6,8-trimethyl-10-phenyldecanoyl, D-gamma-glutamyl, and 2,3-didehydro-N-methylalanyl residues joined into a 25-membered macrocycle. Produced by the cyanobacterium Microcystis aeruginosa, it is the most studied of the microcystins.	3.56	2	0	microcystin	bacterial metabolite; EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; environmental contaminant; xenobiotic
oleic acid Oleic Acid: An unsaturated fatty acid that is the most widely distributed and abundant fatty acid in nature. It is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. (Stedman, 26th ed). oleic acid : An octadec-9-enoic acid in which the double bond at C-9 has Z (cis) stereochemistry.	3.1	5	0	octadec-9-enoic acid	antioxidant; Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; Escherichia coli metabolite; mouse metabolite; plant metabolite; solvent
ferulic acid ferulate : A monocarboxylic acid anion obtained by the deprotonation of the carboxy group of ferulic acid.	7.68	3	0	ferulic acids	anti-inflammatory agent; antioxidant; apoptosis inhibitor; cardioprotective agent; MALDI matrix material; plant metabolite
cocaine Cocaine: An alkaloid ester extracted from the leaves of plants including coca. It is a local anesthetic and vasoconstrictor and is clinically used for that purpose, particularly in the eye, ear, nose, and throat. It also has powerful central nervous system effects similar to the amphetamines and is a drug of abuse. Cocaine, like amphetamines, acts by multiple mechanisms on brain catecholaminergic neurons; the mechanism of its reinforcing effects is thought to involve inhibition of dopamine uptake.. cocaine : A tropane alkaloid obtained from leaves of the South American shrub Erythroxylon coca.	5.33	55	0	benzoate ester; methyl ester; tertiary amino compound; tropane alkaloid	adrenergic uptake inhibitor; central nervous system stimulant; dopamine uptake inhibitor; environmental contaminant; local anaesthetic; mouse metabolite; plant metabolite; serotonin uptake inhibitor; sodium channel blocker; sympathomimetic agent; vasoconstrictor agent; xenobiotic
eicosapentaenoic acid icosapentaenoic acid : Any straight-chain, C20 polyunsaturated fatty acid having five C=C double bonds.. all-cis-5,8,11,14,17-icosapentaenoic acid : An icosapentaenoic acid having five cis-double bonds at positions 5, 8, 11, 14 and 17.	3.26	5	0	icosapentaenoic acid; omega-3 fatty acid	anticholesteremic drug; antidepressant; antineoplastic agent; Daphnia galeata metabolite; fungal metabolite; micronutrient; mouse metabolite; nutraceutical
thapsigargin Thapsigargin: A sesquiterpene lactone found in roots of THAPSIA. It inhibits SARCOPLASMIC RETICULUM CALCIUM-TRANSPORTING ATPASES.. thapsigargin : An organic heterotricyclic compound that is a hexa-oxygenated 6,7-guaianolide isolated fron the roots of Thapsia garganica L., Apiaceae. A potent skin irritant, it is used in traditional medicine as a counter-irritant. Thapsigargin inhibits Ca(2+)-transporting ATPase mediated uptake of calcium ions into sarcoplasmic reticulum and is used in experimentation examining the impacts of increasing cytosolic calcium concentrations.	7.41	2	0	butyrate ester; organic heterotricyclic compound; sesquiterpene lactone	calcium channel blocker; EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor
lycopene [no description available]	3.13	5	0	acyclic carotene	antioxidant; plant metabolite
prostaglandin d2 Prostaglandin D2: The principal cyclooxygenase metabolite of arachidonic acid. It is released upon activation of mast cells and is also synthesized by alveolar macrophages. Among its many biological actions, the most important are its bronchoconstrictor, platelet-activating-factor-inhibitory, and cytotoxic effects.. prostaglandin D2 : A member of the class of prostaglandins D that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9 and 15 and an oxo group at position 11 (the 5Z,9alpha,13E,15S- stereoisomer).	1.98	1	0	prostaglandins D	human metabolite; mouse metabolite
diethylstilbestrol Diethylstilbestrol: A synthetic nonsteroidal estrogen used in the treatment of menopausal and postmenopausal disorders. It was also used formerly as a growth promoter in animals. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), diethylstilbestrol has been listed as a known carcinogen. (Merck, 11th ed). diethylstilbestrol : An olefinic compound that is trans-hex-3-ene in which the hydrogens at positions 3 and 4 have been replaced by p-hydroxyphenyl groups.	5.88	19	0	olefinic compound; polyphenol	antifungal agent; antineoplastic agent; autophagy inducer; calcium channel blocker; carcinogenic agent; EC 1.1.1.146 (11beta-hydroxysteroid dehydrogenase) inhibitor; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; endocrine disruptor; xenoestrogen
zeatin Zeatin: An aminopurine factor in plant extracts that induces cell division. (Grant & Hackh's Chemical Dict, 5th ed)	2.03	1	0	zeatin	plant metabolite
roflumilast [no description available]	7.15	1	0	aromatic ether; benzamides; chloropyridine; cyclopropanes; organofluorine compound	anti-asthmatic drug; phosphodiesterase IV inhibitor
afimoxifene afimoxifene : A tertiary amino compound that is tamoxifen in which the phenyl group which is in a Z- relationship to the ethyl substituent is hydroxylated at the para- position. It is the active metabolite of tamoxifen.	1.98	1	0	phenols; tertiary amino compound	antineoplastic agent; estrogen receptor antagonist; metabolite
decitabine [no description available]	2.15	1	0	2'-deoxyribonucleoside
colfosceril palmitate colfosceril palmitate: used in the treatment of unilateral pulmonary interstitial emphysema; component of Exosurf. 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine : A phosphatidylcholine 32:0 in which the 1- and 2-acyl groups are specified as hexadecanoyl (palmitoyl). A synthetic phospholipid used in liposomes and lipid bilayers to study biological membranes. It is also a major constituent of pulmonary surfactants.	2.58	2	0	1-acyl-2-hexadecanoyl-sn-glycero-3-phosphocholine; phosphatidylcholine 32:0	mouse metabolite; surfactant
iridoids Iridoids: A type of MONOTERPENES, derived from geraniol. They have the general form of cyclopentanopyran, but in some cases, one of the rings is broken as in the case of secoiridoid. They are different from the similarly named iridals (TRITERPENES).	4.9	1	1
dactinomycin Dactinomycin: A compound composed of a two CYCLIC PEPTIDES attached to a phenoxazine that is derived from STREPTOMYCES parvullus. It binds to DNA and inhibits RNA synthesis (transcription), with chain elongation more sensitive than initiation, termination, or release. As a result of impaired mRNA production, protein synthesis also declines after dactinomycin therapy. (From AMA Drug Evaluations Annual, 1993, p2015)	4.46	7	0	actinomycin	mutagen
aphidicolin Aphidicolin: An antiviral antibiotic produced by Cephalosporium aphidicola and other fungi. It inhibits the growth of eukaryotic cells and certain animal viruses by selectively inhibiting the cellular replication of DNA polymerase II or the viral-induced DNA polymerases. The drug may be useful for controlling excessive cell proliferation in patients with cancer, psoriasis or other dermatitis with little or no adverse effect upon non-multiplying cells.. aphidicolin : A tetracyclic diterpenoid that has an tetradecahydro-8,11a-methanocyclohepta[a]naphthalene skeleton with two hydroxymethyl substituents at positions 4 and 9, two methyl substituents at positions 4 and 11b and two hydroxy substituents at positions 3 and 9. An antibiotic with antiviral and antimitotical properties. Aphidicolin is a reversible inhibitor of eukaryotic nuclear DNA replication.	2.9	4	0	tetracyclic diterpenoid	antimicrobial agent; antimitotic; antineoplastic agent; antiviral drug; apoptosis inducer; Aspergillus metabolite; DNA synthesis inhibitor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; fungal metabolite
melphalan Melphalan: An alkylating nitrogen mustard that is used as an antineoplastic in the form of the levo isomer - MELPHALAN, the racemic mixture - MERPHALAN, and the dextro isomer - MEDPHALAN; toxic to bone marrow, but little vesicant action; potential carcinogen.. melphalan : A phenylalanine derivative comprising L-phenylalanine having [bis(2-chloroethyl)amino group at the 4-position on the phenyl ring.	2.4	2	0	L-phenylalanine derivative; nitrogen mustard; non-proteinogenic L-alpha-amino acid; organochlorine compound	alkylating agent; antineoplastic agent; carcinogenic agent; drug allergen; immunosuppressive agent
benzyloxycarbonylleucyl-leucyl-leucine aldehyde benzyloxycarbonylleucyl-leucyl-leucine aldehyde: proteasome inhibitor. N-benzyloxycarbonyl-L-leucyl-L-leucyl-L-leucinal : A tripeptide that is L-leucyl-L-leucyl-L-leucine in which the C-terminal carboxy group has been reduced to the corresponding aldehyde and the N-terminal amino group is protected as its benzyloxycarbonyl derivative.	2.03	1	0	amino aldehyde; carbamate ester; tripeptide	proteasome inhibitor
tenofovir tenofovir (anhydrous) : A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens is replaced by a [(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(isopropyloxycarbonyloxymethyl) ester (disoproxil ester) prodrug is used as the fumaric acid salt in combination therapy for the treatment of HIV infection.	4.9	1	1	nucleoside analogue; phosphonic acids	antiviral drug; drug metabolite; HIV-1 reverse transcriptase inhibitor
riboflavin vitamin B2 : Any member of a group of vitamers that belong to the chemical structural class called flavins that exhibit biological activity against vitamin B2 deficiency. Symptoms associated with vitamin B2 deficiency include glossitis, seborrhea, angular stomaitis, cheilosis and photophobia. The vitamers include riboflavin and its phosphate derivatives (and includes their salt, ionised and hydrate forms).	2.91	4	0	flavin; vitamin B2	anti-inflammatory agent; antioxidant; cofactor; Escherichia coli metabolite; food colouring; fundamental metabolite; human urinary metabolite; mouse metabolite; photosensitizing agent; plant metabolite
potassium permanganate Potassium Permanganate: Permanganic acid (HMnO4), potassium salt. A highly oxidative, water-soluble compound with purple crystals, and a sweet taste. (From McGraw-Hill Dictionary of Scientific and Technical Information, 4th ed)	3.8	3	0
bromochloroacetic acid Keratins: A class of fibrous proteins or scleroproteins that represents the principal constituent of EPIDERMIS; HAIR; NAILS; horny tissues, and the organic matrix of tooth ENAMEL. Two major conformational groups have been characterized, alpha-keratin, whose peptide backbone forms a coiled-coil alpha helical structure consisting of TYPE I KERATIN and a TYPE II KERATIN, and beta-keratin, whose backbone forms a zigzag or pleated sheet structure. alpha-Keratins have been classified into at least 20 subtypes. In addition multiple isoforms of subtypes have been found which may be due to GENE DUPLICATION.. bromochloroacetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is replaced by bromine while a second is replaced by chlorine. A low-melting (27.5-31.5degreeC), hygroscopic crystalline solid, it can be formed during the disinfection (by chlorination) of water that contains bromide ions and organic matter, so can occur in drinking water as a byproduct of the disinfection process.	3.99	14	0	2-bromocarboxylic acid; monocarboxylic acid; organochlorine compound
11-mercaptoundecanoic acid [no description available]	2.07	1	0
diisononyl phthalate diisononyl phthalate: dielectric (electric insulating) fluid. diisononyl phthalate : The diisononyl ester of benzene-1,2-dicarboxylic acid.	2.21	1	0	diester; phthalate ester	plasticiser
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.	2.15	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
elaidic acid [no description available]	7.06	1	0	octadec-9-enoic acid	food component
trans-4-coumaric acid hydroxycinnamic acid : Any member of the class of cinnamic acids carrying one or more hydroxy substituents.. trans-4-coumaric acid : The trans-isomer of 4-coumaric acid.. 4-coumaric acid : A coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring.	2.04	1	0	4-coumaric acid	food component; mouse metabolite; plant metabolite
anethole anethole: an isomer of estragole; structurally similar to CAPSAICIN; has some neurological and insecticidal and skin absorption effects; RN given refers to unspecified stereoisomer. anethole : A monomethoxybenzene that is methoxybenzene substituted by a prop-1-en-1-yl group at position 4.. trans-anethole : The trans-stereoisomer of anethole.	2.15	1	0	anethole	flavouring agent
geraniol [no description available]	5.04	2	1	3,7-dimethylocta-2,6-dien-1-ol; monoterpenoid; primary alcohol	allergen; fragrance; plant metabolite; volatile oil component
glycosides [no description available]	2.1	1	0
chalcone trans-chalcone : The trans-isomer of chalcone.	7.68	3	0	chalcone	EC 3.2.1.1 (alpha-amylase) inhibitor
isomethyleugenol Methylation: Addition of methyl groups. In histo-chemistry methylation is used to esterify carboxyl groups and remove sulfate groups by treating tissue sections with hot methanol in the presence of hydrochloric acid. (From Stedman, 25th ed)	5.89	19	0	isomethyleugenol
isosafrole isosafrole: RN given refers to cpd without isomeric designation	3.07	5	0	benzodioxoles
beta-ionone beta-ionone: stimulator of carotenogenesis; carotenoid inhibitor; intermediate in synthesis of Vit A; RN given refers to cpd without isomeric designation; structure. beta-ionone : An ionone that is but-3-en-2-one substituted by a 2,6,6-trimethylcyclohex-1-en-1-yl group at position 4.	7.07	1	0	ionone	antioxidant; fragrance
retinaldehyde Retinaldehyde: A diterpene derived from the carotenoid VITAMIN A which functions as the active component of the visual cycle. It is the prosthetic group of RHODOPSIN (i.e., covalently bonded to ROD OPSIN as 11-cis-retinal). When stimulated by visible light, rhodopsin transforms this cis-isomer of retinal to the trans-isomer (11-trans-retinal). This transformation straightens-out the bend of the retinal molecule and causes a change in the shape of rhodopsin triggering the visual process. A series of energy-requiring enzyme-catalyzed reactions convert the 11-trans-retinal back to the cis-isomer.. all-trans-retinal : A retinal in which all four exocyclic double bonds have E- (trans-) geometry.	2.94	4	0	retinal; vitamin A	gap junctional intercellular communication inhibitor; human metabolite; mouse metabolite
piperine piperine : A N-acylpiperidine that is piperidine substituted by a (1E,3E)-1-(1,3-benzodioxol-5-yl)-5-oxopenta-1,3-dien-5-yl group at the nitrogen atom. It is an alkaloid isolated from the plant Piper nigrum.	3.97	13	0	benzodioxoles; N-acylpiperidine; piperidine alkaloid; tertiary carboxamide	food component; human blood serum metabolite; NF-kappaB inhibitor; plant metabolite
retinol acetate retinol acetate: structure given in first source	1.96	1	0	acetate ester
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	4.84	32	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.	7.03	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
gw9662 2-chloro-5-nitrobenzanilide: pretreatment of peroxisome proliferator activated receptors with GW9662 results in the irreversible loss of ligand binding	2.04	1	0	benzamides
glucobrassicin glucobrassicin: isolated from Brussels sprouts; structure given in first source. glucobrassicin : An indolylmethylglucosinolic acid that is 1-thio-beta-D-glucopyranose having a 2-(1H-indol-3-yl)-N-(sulfooxy)ethanimidoyl group attached to the anomeric sulfur.	4.14	1	0	indolyl carbohydrate; indolylmethylglucosinolic acid
polidocanol Polidocanol: An alkyl polyglycol ether of LAURYL ALCOHOL, chemically defined as an alcohol ethoxylate having an average alkyl chain of 12–14 carbon atoms, and an ethylene oxide chain of 9 ethylene oxide units. It is used as a detergent, and medically as a local anesthetic, and as a sclerosing agent for the treatment of ESOPHAGEAL AND GASTRIC VARICES and VARICOSE VEINS.. polidocanol : A hydroxypolyether that is nonaethylene glycol in which one of the terminal hydroxy functions is substituted by a lauryl (dodecyl) group.	2.02	1	0	hydroxypolyether	hepatotoxic agent; nonionic surfactant; sclerotherapy agent
sodium metabisulfite sodium metabisulfite: request from searcher; RN given refers to disulfurous acid, di-Na salt. sodium disulfite : An inorganic sodium salt composed of sodium and disulfite ions in a 2:1 ratio.	1.97	1	0	inorganic sodium salt	food antioxidant
sesquiterpenes [no description available]	2.1	1	0
mercaptopurine Mercaptopurine: An antimetabolite antineoplastic agent with immunosuppressant properties. It interferes with nucleic acid synthesis by inhibiting purine metabolism and is used, usually in combination with other drugs, in the treatment of or in remission maintenance programs for leukemia.. purine-6-thiol : A thiol that is the tautomer of mercaptopurine.. mercaptopurine : A member of the class of purines that is 6,7-dihydro-1H-purine carrying a thione group at position 6. An adenine analogue, it is used in the treatment of acute lymphocytic leukemia (ALL), chronic myeloid leukemia (CML), Crohn's disease, and ulcerative colitis.	1.98	1	0	aryl thiol; purines; thiocarbonyl compound	anticoronaviral agent; antimetabolite; antineoplastic agent
3,3',4,5'-tetrahydroxystilbene 3,3',4,5'-tetrahydroxystilbene: demethyl derivative of isorhapontigenin; structure in first source; a Syk kinase inhibitor; found in heartwood of FABACEAE; inhibitor of photosynthesis in spinach chloroplasts; may be inhibitor of plant growth; RN given refers to (E)-isomer. piceatannol : A stilbenol that is trans-stilbene in which one of the phenyl groups is substituted by hydroxy groups at positions 3 and 4, while the other phenyl group is substituted by hydroxy groups at positions 3 and 5.	2.6	1	0	catechols; polyphenol; resorcinols; stilbenol	antineoplastic agent; apoptosis inducer; geroprotector; hypoglycemic agent; plant metabolite; protein kinase inhibitor; tyrosine kinase inhibitor
2-mercaptonicotinic acid 2-mercaptonicotinic acid: structure given in first source	2.01	1	0
3',4'-dimethoxyflavone [no description available]	2.73	3	0
6,2',4'-trimethoxyflavone 6,2',4'-trimethoxyflavone: structure in first source	2.05	1	0
caffeic acid trans-caffeic acid : The trans-isomer of caffeic acid.	2.38	2	0	caffeic acid	geroprotector; mouse metabolite
isoeugenol trans-isoeugenol : The trans-stereoisomer of isoeugenol.	2.45	2	0	isoeugenol	plant metabolite
cotinine Cotinine: The N-glucuronide conjugate of cotinine is a major urinary metabolite of NICOTINE. It thus serves as a biomarker of exposure to tobacco SMOKING. It has CNS stimulating properties.. (-)-cotinine : An N-alkylpyrrolidine that consists of N-methylpyrrolidinone bearing a pyridin-3-yl substituent at position C-5 (the 5S-enantiomer). It is an alkaloid commonly found in Nicotiana tabacum.	5.76	20	1	N-alkylpyrrolidine; pyridines; pyrrolidin-2-ones; pyrrolidine alkaloid	antidepressant; biomarker; human xenobiotic metabolite; plant metabolite
dieldrin Dieldrin: An organochlorine insecticide whose use has been cancelled or suspended in the United States. It has been used to control locusts, tropical disease vectors, in termite control by direct soil injection, and non-food seed and plant treatment. (From HSDB). dieldrin : An organochlorine compound resulting from the epoxidation of the double bond of aldrin. It is the active metabolite of the proinsecticde aldrin.	2.01	1	0	epoxide; organochlorine compound; organochlorine insecticide	carcinogenic agent; xenobiotic
curcumin Curcumin: A yellow-orange dye obtained from tumeric, the powdered root of CURCUMA longa. It is used in the preparation of curcuma paper and the detection of boron. Curcumin appears to possess a spectrum of pharmacological properties, due primarily to its inhibitory effects on metabolic enzymes.. curcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa.	8.9	39	1	aromatic ether; beta-diketone; diarylheptanoid; enone; polyphenol	anti-inflammatory agent; antifungal agent; antineoplastic agent; biological pigment; contraceptive drug; dye; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; EC 1.8.1.9 (thioredoxin reductase) inhibitor; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; flavouring agent; food colouring; geroprotector; hepatoprotective agent; immunomodulator; iron chelator; ligand; lipoxygenase inhibitor; metabolite; neuroprotective agent; nutraceutical; radical scavenger
capsaicin ALGRX-4975: an injectable capsaicin (TRPV1 receptor agonist) formulation for longlasting pain relief. capsaicinoid : A family of aromatic fatty amides produced as secondary metabolites by chilli peppers.	3.55	8	0	capsaicinoid	non-narcotic analgesic; TRPV1 agonist; voltage-gated sodium channel blocker
terbinafine [no description available]	2.07	1	0	acetylenic compound; allylamine antifungal drug; enyne; naphthalenes; tertiary amine	EC 1.14.13.132 (squalene monooxygenase) inhibitor; P450 inhibitor; sterol biosynthesis inhibitor
chlorogenic acid caffeoylquinic acid: Antiviral Agent; structure in first source. chlorogenate : A monocarboxylic acid anion that is the conjugate base of chlorogenic acid; major species at pH 7.3.	2.9	4	0	cinnamate ester; tannin	food component; plant metabolite
thioguanine anhydrous Thioguanine: An antineoplastic compound which also has antimetabolite action. The drug is used in the therapy of acute leukemia.. tioguanine : A 2-aminopurine that is the 6-thiono derivative of 2-amino-1,9-dihydro-6H-purine. Incorporates into DNA and inhibits synthesis. Used in the treatment of leukaemia.	3.47	8	0	2-aminopurines	anticoronaviral agent; antimetabolite; antineoplastic agent
thiobarbituric acid thiobarbituric acid: RN given refers to parent cpd. 2-thiobarbituric acid : A barbiturate, the structure of which is that of barbituric acid in which the oxygen at C-2 is replaced by sulfur.	1.98	1	0	barbiturates	allergen; reagent
thiourea Thiourea: A photographic fixative used also in the manufacture of resins. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), this substance may reasonably be anticipated to be a carcinogen (Merck Index, 9th ed). Many of its derivatives are ANTITHYROID AGENTS and/or FREE RADICAL SCAVENGERS.. thiourea : The simplest member of the thiourea class, consisting of urea with the oxygen atom substituted by sulfur.	2.68	3	0	one-carbon compound; thioureas; ureas	antioxidant; chromophore
indigo carmine Indigo Carmine: Indolesulfonic acid used as a dye in renal function testing for the detection of nitrates and chlorates, and in the testing of milk.. indigo carmine : An organic sodium salt resulting from the formal condensation of indigo carmine (acid form) with two equivalents of sodium hydroxide. It is an indicator at pH 11.5-14, changing from blue to yellow.	2.43	2	0
thioacetamide Thioacetamide: A crystalline compound used as a laboratory reagent in place of HYDROGEN SULFIDE. It is a potent hepatocarcinogen.. thioacetamide : A thiocarboxamide consiting of acetamide having the oxygen replaced by sulfur.	2.43	2	0	thiocarboxamide	hepatotoxic agent
brij-58 Cetomacrogol: Non-ionic surfactant of the polyethylene glycol family. It is used as a solubilizer and emulsifying agent in foods, cosmetics, and pharmaceuticals, often as an ointment base, and also as a research tool.	1.96	1	0
6-thioguanosine 6-thioguanosine: RN given refers to cpd without isomeric designation	2.25	1	0	purine nucleoside
1,3-dihydroxy-4,4,5,5-tetramethyl-2-(4-carboxyphenyl)tetrahydroimidazole 1,3-dihydroxy-4,4,5,5-tetramethyl-2-(4-carboxyphenyl)tetrahydroimidazole: intermediate in the synthesis of imidazolineoxyl N-oxides; partial structure given in first source	2.17	1	0	benzoic acid; imidazolines; organic radical	apoptosis inhibitor; radical scavenger
tamoxifen [no description available]	4.6	8	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
hydroxypropyl-gamma-cyclodextrin [no description available]	2.07	1	0
sodium taurodeoxycholate Taurodeoxycholic Acid: A bile salt formed in the liver by conjugation of deoxycholate with taurine, usually as the sodium salt. It is used as a cholagogue and choleretic, also industrially as a fat emulsifier.. taurodeoxycholic acid : A bile acid taurine conjugate of deoxycholic acid.. taurodeoxycholate : An organosulfonate oxoanion that is the conjugate base of taurodeoxycholic acid.	1.99	1	0	bile acid taurine conjugate	human metabolite
nadp [no description available]	8.28	54	1
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	1	0
sc 514 SC 514: inhibits IkappaB kinase-2; structure in first source	2.04	1	0	ring assembly; thiophenes
nitrobenzanthrone 3-nitrobenzanthrone: mutagenic environmental contaminant; structure in first source	3.36	6	0	phenanthrenes
nabam mancozeb: complex of zinc & maneb, containing 20% manganese & 2.5% zinc. mancozeb : A mixture composed from maneb and zineb, which is used as a broad-spectrum contact fungicide.. ethylenebis(dithiocarbamic acid) : A dithiocarbamic acid resulting from the formal addition of a molecule of carbon disulfide to each amino group of ethylenediamine.	2.73	3	0	dithiocarbamic acids
toremifene Toremifene: A first generation selective estrogen receptor modulator (SERM). Like TAMOXIFEN, it is an estrogen agonist for bone tissue and cholesterol metabolism but is antagonistic on mammary and uterine tissue.	1.99	1	0	aromatic ether; organochlorine compound; tertiary amine	antineoplastic agent; bone density conservation agent; estrogen antagonist; estrogen receptor modulator
u 0126 U 0126: protein kinase kinase inhibitor; structure in first source	2.51	2	0	aryl sulfide; dinitrile; enamine; substituted aniline	antineoplastic agent; antioxidant; apoptosis inducer; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; osteogenesis regulator; vasoconstrictor agent
laccase Laccase: A copper-containing oxidoreductase enzyme that catalyzes the oxidation of 4-benzenediol to 4-benzosemiquinone. It also has activity towards a variety of O-quinols and P-quinols. It primarily found in FUNGI and is involved in LIGNIN degradation, pigment biosynthesis and detoxification of lignin-derived products.	3.9	11	0
lithium Lithium: An element in the alkali metals family. It has the atomic symbol Li, atomic number 3, and atomic weight [6.938; 6.997]. Salts of lithium are used in treating BIPOLAR DISORDER.	1.96	1	0	alkali metal atom
zineb Zineb: An agricultural fungicide of the dithiocarbamate class. It has relatively low toxicity and there is little evidence of human injury from exposure.. zineb : A polymeric complex of zinc with the ethylene bis(dithiocarbamate) anionic ligand. Formerly used as an agricultural fungicide for the control of downy mildews and rusts, its use is no longer permitted in the US or the EU.	2.94	4	0	dithiocarbamate salt; macromolecule; zinc coordination entity	antifungal agrochemical
cobaltous chloride cobaltous chloride: RN given refers to unlabeled cpd; RN in Chemline for cobalt trichloride: 10241-04-0; RN for 60-labeled cpd: 14543-09-0; RN for 57-labeled cpd: 164113-89-1; RN for 58-labeled cpd: 29377-09-1; structure. cobalt dichloride : A cobalt salt in which the cobalt metal is in the +2 oxidation state and the counter-anion is chloride. It is used as an indicator for water in desiccants.	2.4	2	0	cobalt salt; inorganic chloride	allergen; calcium channel blocker; sensitiser; two-colour indicator
nitrogen dioxide Nitrogen Dioxide: Nitrogen oxide (NO2). A highly poisonous gas. Exposure produces inflammation of lungs that may only cause slight pain or pass unnoticed, but resulting edema several days later may cause death. (From Merck, 11th ed) It is a major atmospheric pollutant that is able to absorb UV light that does not reach the earth's surface.	4.37	6	0	nitrogen oxide
maneb Maneb: Manganese derivative of ethylenebisdithiocarbamate. It is used in agriculture as a fungicide and has been shown to cause irritation to the eyes, nose, skin, and throat.. maneb : A polymeric complex of manganese with the ethylene bis(dithiocarbamate) anionic ligand. An agrochemical fungicide, it is used to control a variety of diseases including blight, leaf spot, rust, downy mildew and scab.	2.73	3	0
gestodene Gestodene: synthetic steroid with progestational activity; RN given refers to (17alpha)-isomer	1.98	1	0	steroid	estrogen
15,16-dihydro-11-methylcyclopenta(a)phenanthren-17-one 15,16-dihydro-11-methylcyclopenta(a)phenanthren-17-one: structure	1.96	1	0
benzo(a)pyrene-3-o-glucuronide benzo(a)pyrene-3-O-glucuronide: RN given refers to (D)-isomer	7.37	2	0
glycodeoxycholic acid Glycodeoxycholic Acid: A bile salt formed in the liver by conjugation of deoxycholate with glycine, usually as the sodium salt. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and choleretic.. glycodeoxycholic acid : A bile acid glycine conjugate of deoxycholic acid.	1.99	1	0	bile acid glycine conjugate	human metabolite
11,12-dihydroxy-13,14-epoxy-11,12,13,14-tetrahydrodibenzo(a,l)pyrene 11,12-dihydroxy-13,14-epoxy-11,12,13,14-tetrahydrodibenzo(a,l)pyrene: RN refers to (alpha,beta,beta,beta)-stereoisomer; structure in first source	2.05	1	0
rtki cpd RTKI cpd: preferentially inhibits human glioma cells expressing truncated rather than wild-type epidermal growth factor receptors	2.03	1	0
cystine [no description available]	5.13	3	1
erysolin [no description available]	7.04	1	0
amanitins Amanitins: Cyclic peptides extracted from carpophores of various mushroom species. They are potent inhibitors of RNA polymerases in most eukaryotic species, blocking the production of mRNA and protein synthesis. These peptides are important in the study of transcription. Alpha-amanitin is the main toxin from the species Amanitia phalloides, poisonous if ingested by humans or animals.	1.96	1	0
ginsenosides ginsenoside : Triterpenoid saponins with a dammarane-like skeleton originally isolated from ginseng (Panax) species. Use of the term has been extended to include semi-synthetic derivatives.	3.18	5	0
tecoflex Tecoflex: RN given refers to cpd with unknown MF	2.01	1	0
ovalbumin Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.	3.55	8	0
sodium dodecyl sulfate Sodium Dodecyl Sulfate: An anionic surfactant, usually a mixture of sodium alkyl sulfates, mainly the lauryl; lowers surface tension of aqueous solutions; used as fat emulsifier, wetting agent, detergent in cosmetics, pharmaceuticals and toothpastes; also as research tool in protein biochemistry.. sodium dodecyl sulfate : An organic sodium salt that is the sodium salt of dodecyl hydrogen sulfate.	2.94	4	0	organic sodium salt	detergent; protein denaturant
mtt formazan MTT formazan: a blue MEM-insoluble mitochondrial byproduct; used to determine viability of cells with active mitochondrial dehydrogenase enzymes	2	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.	1.97	1	0
17-ketosteroids 17-Ketosteroids: Steroids that contain a ketone group at position 17.. 17-oxo steroid : Any oxo steroid carrying the oxo group at position 17.	1.97	1	0
naphthoquinones Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.	2.93	4	0
osteoprotegerin Osteoprotegerin: A secreted member of the TNF receptor superfamily that negatively regulates osteoclastogenesis. It is a soluble decoy receptor of RANK LIGAND that inhibits both CELL DIFFERENTIATION and function of OSTEOCLASTS by inhibiting the interaction between RANK LIGAND and RECEPTOR ACTIVATOR OF NUCLEAR FACTOR-KAPPA B.	2.11	1	0	long-chain fatty acid
rhodamine 123 Rhodamine 123: A fluorescent probe with low toxicity which is a potent substrate for ATP BINDING CASSETTE TRANSPORTER, SUBFAMILY B, MEMBER 1 and the bacterial multidrug efflux transporter. It is used to assess mitochondrial bioenergetics in living cells and to measure the efflux activity of ATP BINDING CASSETTE TRANSPORTER, SUBFAMILY B, MEMBER 1 in both normal and malignant cells. (Leukemia 1997;11(7):1124-30). rhodamine 123(1+) : A cationic fluorescent dye derived from 9-phenylxanthene.	2.95	4	0	organic cation; xanthene dye	fluorochrome
1,2-diamino-4-nitrobenzene 1,2-diamino-4-nitrobenzene: reagent for determination of selenium in milk with gas chromatograph. 4-nitro-1,2-phenylenediamine : The primary amino compound that is 1,2-phenylenediamine (o-phenylenediamine) substituted at the 4- (para-) position by a nitro group.	3.09	5	0	C-nitro compound; primary amino compound
diethyl maleate diethyl maleate : A maleate ester resulting from the formal condensation of both carboxy groups of maleic acid with ethanol. A colourless liquid at room temperature (m.p. -10degreeC) with boiling point 220degreeC at 1 atm., it is commonly used as a dienophile for Diels-Alder-type cycloaddition reactions in organic synthesis.	2.03	1	0	ethyl ester; maleate ester	glutathione depleting agent
ku 55933 2-morpholin-4-yl-6-thianthren-1-yl-pyran-4-one: specific inhibitor of the ataxia-telangiectasia mutated kinase ATM; structure in first source	2.11	1	0
sphingosine sphing-4-enine : A sphingenine in which the C=C double bond is located at the 4-position.. sphingenine : A 2-aminooctadecene-1,3-diol having (2S,3R)-configuration.. sphingoid : Sphinganine, its homologs and stereoisomers, and the hydroxy and unsaturated derivatives of these compounds.. 2-aminooctadec-4-ene-1,3-diol : A 2-aminooctadecene-1,3-diol having its double bond at position 4.	1.98	1	0	sphing-4-enine	human metabolite; mouse metabolite
quercetin [no description available]	4.88	34	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
bilirubin [no description available]	9.02	4	0	biladienes; dicarboxylic acid	antioxidant; human metabolite; mouse metabolite
dinoprostone prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.	4.09	15	0	prostaglandins E	human metabolite; mouse metabolite; oxytocic
dinoprost Dinoprost: A naturally occurring prostaglandin that has oxytocic, luteolytic, and abortifacient activities. Due to its vasocontractile properties, the compound has a variety of other biological actions.. prostaglandin F2alpha : A prostaglandins Falpha that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15. It is a naturally occurring prostaglandin used to induce labor.	3.62	9	0	monocarboxylic acid; prostaglandins Falpha	human metabolite; mouse metabolite
biochanin a [no description available]	2.67	3	0	4'-methoxyisoflavones; 7-hydroxyisoflavones	antineoplastic agent; EC 3.5.1.99 (fatty acid amide hydrolase) inhibitor; phytoestrogen; plant metabolite; tyrosine kinase inhibitor
sterigmatocystin [no description available]	1.97	1	0	sterigmatocystins	metabolite
apigenin Chamomile: Common name for several daisy-like plants (MATRICARIA; TRIPLEUROSPERMUM; ANTHEMIS; CHAMAEMELUM) native to Europe and Western Asia, now naturalized in the United States and Australia.	7.92	4	0	trihydroxyflavone	antineoplastic agent; metabolite
luteolin [no description available]	2.8	3	0	3'-hydroxyflavonoid; tetrahydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; apoptosis inducer; c-Jun N-terminal kinase inhibitor; EC 2.3.1.85 (fatty acid synthase) inhibitor; immunomodulator; nephroprotective agent; plant metabolite; radical scavenger; vascular endothelial growth factor receptor antagonist
linoleic acid Linoleic Acid: A doubly unsaturated fatty acid, occurring widely in plant glycosides. It is an essential fatty acid in mammalian nutrition and is used in the biosynthesis of prostaglandins and cell membranes. (From Stedman, 26th ed). linoleic acid : An octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry.	8.49	8	0	octadecadienoic acid; omega-6 fatty acid	algal metabolite; Daphnia galeata metabolite; plant metabolite
calcitriol dihydroxy-vitamin D3: as a major in vitro metabolite of 1alpha,25-dihydroxyvitamin D3, produced in primary cultures of neonatal human keratinocytes	2.4	2	0	D3 vitamins; hydroxycalciol; triol	antineoplastic agent; antipsoriatic; bone density conservation agent; calcium channel agonist; calcium channel modulator; hormone; human metabolite; immunomodulator; metabolite; mouse metabolite; nutraceutical
quercitrin [no description available]	2	1	0	alpha-L-rhamnoside; monosaccharide derivative; quercetin O-glycoside; tetrahydroxyflavone	antileishmanial agent; antioxidant; EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.14.18.1 (tyrosinase) inhibitor; plant metabolite
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.	3.36	7	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.	4.6	26	0	carotenoid beta-end derivative; cyclic carotene	antioxidant; biological pigment; cofactor; ferroptosis inhibitor; human metabolite; mouse metabolite; plant metabolite; provitamin A
leukotriene b4 Leukotriene B4: The major metabolite in neutrophil polymorphonuclear leukocytes. It stimulates polymorphonuclear cell function (degranulation, formation of oxygen-centered free radicals, arachidonic acid release, and metabolism). (From Dictionary of Prostaglandins and Related Compounds, 1990). leukotriene B4 : A leukotriene composed of (6Z,8E,10E,14Z)-icosatetraenoic acid having (5S)- and (12R)-hydroxy substituents. It is a lipid mediator of inflammation that is generated from arachidonic acid via the 5-lipoxygenase pathway.	2.4	2	0	dihydroxy monocarboxylic acid; hydroxy polyunsaturated fatty acid; leukotriene; long-chain fatty acid	human metabolite; mouse metabolite; plant metabolite; vasoconstrictor agent
thromboxane a2 Thromboxane A2: An unstable intermediate between the prostaglandin endoperoxides and thromboxane B2. The compound has a bicyclic oxaneoxetane structure. It is a potent inducer of platelet aggregation and causes vasoconstriction. It is the principal component of rabbit aorta contracting substance (RCS).. thromboxane A2 : A thromboxane which is produced by activated platelets and has prothrombotic properties: it stimulates activation of new platelets as well as increases platelet aggregation.	3.46	2	0	epoxy monocarboxylic acid; thromboxanes A	mouse metabolite
retinol palmitate retinol palmitate: RN given refers to parent cpd; structure. retinyl palmitate : A palmitate ester of retinol with undefined geometry about the C=C bonds.. all-trans-retinyl palmitate : An all-trans-retinyl ester obtained by formal condensation of the carboxy group of palmitic (hexadecanoic acid) with the hydroxy group of all-trans-retinol. It is used in cosmetic products to treat various skin disorders such as acne, skin aging, wrinkles, dark spots, and also protect against psoriasis.	2.36	2	0	all-trans-retinyl ester; retinyl palmitate	antioxidant; Escherichia coli metabolite; human xenobiotic metabolite
hymecromone Hymecromone: A coumarin derivative possessing properties as a spasmolytic, choleretic and light-protective agent. It is also used in ANALYTICAL CHEMISTRY TECHNIQUES for the determination of NITRIC ACID.	2.39	2	0	hydroxycoumarin	antineoplastic agent; hyaluronic acid synthesis inhibitor
8,11,14-eicosatrienoic acid 8,11,14-Eicosatrienoic Acid: A 20-carbon-chain fatty acid, unsaturated at positions 8, 11, and 14. It differs from arachidonic acid, 5,8,11,14-eicosatetraenoic acid, only at position 5.. all-cis-icosa-8,11,14-trienoic acid : An icosatrienoic acid having three cis double bonds at positions 8, 11 and 14.	1.98	1	0	fatty acid 20:3; long-chain fatty acid	fungal metabolite; human metabolite; nutraceutical
rosin rosin: Resin from plant. Do not confuse with the specific compound: 3-phenyl-2-propenyl-(E)-beta-D-glucopyranoside, also know as rosin.	1.98	1	0
furylfuramide Furylfuramide: Used formerly as antimicrobial food additive. It causes mutations in many cell cultures and may be carcinogenic.. (Z)-2-(2-furyl)-3-(5-nitro-2-furyl)acrylamide : A member of the class of acrylamides that is acrylamide which is substituted at positions 2 and 3 by 2-furyl and 5-nitro-2-furyl groups, respectively (the trans isomer). Formerly used as a food preservative, it was withdrawn from the market following suspicions of carcenogenicity.	2.41	2	0	acrylamides; C-nitro compound; nitrofuran antibiotic; primary carboxamide
alprostadil [no description available]	2.89	4	0	prostaglandins E	anticoagulant; human metabolite; platelet aggregation inhibitor; vasodilator agent
vitamin d 2 Ergocalciferols: Derivatives of ERGOSTEROL formed by ULTRAVIOLET RAYS breaking of the C9-C10 bond. They differ from CHOLECALCIFEROL in having a double bond between C22 and C23 and a methyl group at C24.. vitamin D2 : A vitamin D supplement and has been isolated from alfalfa.	2.04	1	0	hydroxy seco-steroid; seco-ergostane; vitamin D	bone density conservation agent; nutraceutical; plant metabolite; rodenticide
cholecalciferol Cholecalciferol: Derivative of 7-dehydroxycholesterol formed by ULTRAVIOLET RAYS breaking of the C9-C10 bond. It differs from ERGOCALCIFEROL in having a single bond between C22 and C23 and lacking a methyl group at C24.. calciol : A hydroxy seco-steroid that is (5Z,7E)-9,10-secocholesta-5,7,10(19)-triene in which the pro-S hydrogen at position 3 has been replaced by a hydroxy group. It is the inactive form of vitamin D3, being hydroxylated in the liver to calcidiol (25-hydroxyvitamin D3), which is then further hydroxylated in the kidney to give calcitriol (1,25-dihydroxyvitamin D3), the active hormone.	3.25	6	0	D3 vitamins; hydroxy seco-steroid; seco-cholestane; secondary alcohol; steroid hormone	geroprotector; human metabolite
rutin Hydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders.	10.5	4	1	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite
kaempferol [no description available]	2.45	2	0	7-hydroxyflavonol; flavonols; tetrahydroxyflavone	antibacterial agent; geroprotector; human blood serum metabolite; human urinary metabolite; human xenobiotic metabolite; plant metabolite
dehydroretinal all-trans-dehydroretinal : A retinal which contains an additional double bond between the 3 and 4 positions of the six-membered ring, and in which all of the double bonds in the side chain have the E-configuration.	2.02	1	0	retinals
6-ketoprostaglandin f1 alpha 6-Ketoprostaglandin F1 alpha: The physiologically active and stable hydrolysis product of EPOPROSTENOL. Found in nearly all mammalian tissue.. 6-oxoprostaglandin F1alpha : A prostaglandin Falpha that is prostaglandin F1alpha bearing a keto substituent at the 6-position.	2.67	3	0	prostaglandins Falpha	human metabolite; mouse metabolite
lipoxin a4 lipoxin A4: an antifibrolytic agent; structure given in first source; a role in ASPIRIN antiinflammatory activity. lipoxin A4 : A C20 hydroxy fatty acid having (5S)-, (6R)- and (15S)-hydroxy groups as well as (7E)- (9E)-, (11Z)- and (13E)-double bonds.	2.21	1	0	hydroxy polyunsaturated fatty acid; lipoxin; long-chain fatty acid	human metabolite; metabolite
gamma-linolenic acid gamma-Linolenic Acid: An omega-6 fatty acid produced in the body as the delta 6-desaturase metabolite of linoleic acid. It is converted to dihomo-gamma-linolenic acid, a biosynthetic precursor of monoenoic prostaglandins such as PGE1. (From Merck Index, 11th ed). gamma-linolenic acid : A C18, omega-6 acid fatty acid comprising a linolenic acid having cis- double bonds at positions 6, 9 and 12.	2.68	3	0	linolenic acid; omega-6 fatty acid	human metabolite; mouse metabolite; plant metabolite
prostaglandin f3alpha prostaglandin F3alpha : A prostaglandin Falpha that is prosta-5,13,17-trien-1-oic acid carrying three hydroxy substituents at positions 9alpha, 11alpha and 15.	2.13	1	0	prostaglandins Falpha
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.	1.97	1	0	harmala alkaloid	anti-HIV agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; metabolite
genistein [no description available]	3.38	7	0	7-hydroxyisoflavones	antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; geroprotector; human urinary metabolite; phytoestrogen; plant metabolite; tyrosine kinase inhibitor
amphotericin b Amphotericin B: Macrolide antifungal antibiotic produced by Streptomyces nodosus obtained from soil of the Orinoco river region of Venezuela.. amphotericin B : A macrolide antibiotic used to treat potentially life-threatening fungal infections.	2.11	1	0	antibiotic antifungal drug; macrolide antibiotic; polyene antibiotic	antiamoebic agent; antiprotozoal drug; bacterial metabolite
pulmicort Budesonide: A glucocorticoid used in the management of ASTHMA, the treatment of various skin disorders, and allergic RHINITIS.. budesonide : A glucocorticoid steroid having a highly oxygenated pregna-1,4-diene structure. It is used mainly in the treatment of asthma and non-infectious rhinitis and for treatment and prevention of nasal polyposis.	4.45	8	0	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; cyclic acetal; glucocorticoid; primary alpha-hydroxy ketone	anti-inflammatory drug; bronchodilator agent; drug allergen
kava Kava: Dried rhizome and roots of Piper methysticum, a shrub native to Oceania and known for its anti-anxiety and sedative properties. Heavy usage results in some adverse effects. It contains ALKALOIDS; LACTONES; kawain, methysticin, mucilage, STARCH, and yangonin. Kava is also the name of the pungent beverage prepared from the plant's roots.	2.76	3	0
astaxanthine astaxanthine: a keto form of carotene; pigment in flesh of Scottish salmon (Salmo salar) crustacoa-lobster (Homarus gammarus, flamingo feathers; structure; a carotenoid without vitamin A activity, has shown anti-oxidant and anti-inflammatory activities. astaxanthin : A carotenone that consists of beta,beta-carotene-4,4'-dione bearing two hydroxy substituents at positions 3 and 3' (the 3S,3'S diastereomer). A carotenoid pigment found mainly in animals (crustaceans, echinoderms) but also occurring in plants. It can occur free (as a red pigment), as an ester, or as a blue, brown or green chromoprotein.	2.06	1	0	carotenol; carotenone	animal metabolite; anticoagulant; antioxidant; food colouring; plant metabolite
canthaxanthin Canthaxanthin: A trans-carotenoid pigment widely distributed in nature. The compound is used as an oral suntanning agent and as a food and drug coloring agent. Oral ingestion of the compound causes canthaxanthin retinopathy.. canthaxanthin : A carotenone that consists of beta,beta-carotene bearing two oxo substituents at positions 4 and 4'.	7.88	4	0	carotenone	biological pigment; Escherichia coli metabolite; food colouring; fungal metabolite
fucoxanthin fucoxanthin: RN given refers to (3S,3'S,5R,5'R,6S,6'R)-isomer. fucoxanthin : An epoxycarotenol that is found in brown seaweed and which exhibits anti-cancer, anti-diabetic, anti-oxidative and neuroprotective properties.	7.21	1	0
lutein Lutein: A xanthophyll found in the major LIGHT-HARVESTING PROTEIN COMPLEXES of plants. Dietary lutein accumulates in the MACULA LUTEA.. xanthophyll : A subclass of carotenoids consisting of the oxygenated carotenes.	7.46	2	0	carotenol	food colouring; plant metabolite
mezerein mezerein: toxic component of plant Daphne mezereum with anti-leukemic activity against P-388 & P-1210 in mice; can act as a tumor promoter; RN given refers to (12beta(E,E))-isomer; structure	2.38	2	0	diterpenoid
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.	1.97	1	0	harmala alkaloid; indole alkaloid fundamental parent; indole alkaloid	anti-HIV agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; plant metabolite
esculetin esculetin: used in filters for absorption of ultraviolet light; structure. esculetin : A hydroxycoumarin that is umbelliferone in which the hydrogen at position 6 is substituted by a hydroxy group. It is used in filters for absorption of ultraviolet light.	2	1	0	hydroxycoumarin	antioxidant; plant metabolite; ultraviolet filter
ostruthin [no description available]	1.99	1	0	terpene lactone	metabolite
7-hydroxycoumarin 7-oxycoumarin: derivatives have anti-oxidant properties. umbelliferone : A hydroxycoumarin that is coumarin substituted by a hydroxy group ay position 7.	2.42	2	0	hydroxycoumarin	fluorescent probe; food component; plant metabolite
oleuropein oleuropein: iridoid isolated from leaves and fruit of Olea and Ligustrum (Oleaceae). oleuropein : A secoiridoid glycoside that is the methyl ester of 3,4-dihydro-2H-pyran-5-carboxylic acid which is substituted at positions 2, 3, and 4 by hydroxy, ethylidene, and carboxymethyl groups, respectively and in which the anomeric hydroxy group at position 2 has been converted into its beta-D-glucoside and the carboxylic acid moiety of the carboxymethyl substituent has been converted to the corresponding 3,4-dihydroxyphenethyl ester (the 2S,3E,4S stereoisomer). The most important phenolic compound present in olive cultivars.	4.9	1	1	beta-D-glucoside; catechols; diester; methyl ester; pyrans; secoiridoid glycoside	anti-inflammatory agent; antihypertensive agent; antineoplastic agent; antioxidant; apoptosis inducer; NF-kappaB inhibitor; nutraceutical; plant metabolite; radical scavenger
baicalein [no description available]	3.3	6	0	trihydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antibacterial agent; anticoronaviral agent; antifungal agent; antineoplastic agent; antioxidant; apoptosis inducer; EC 1.13.11.31 (arachidonate 12-lipoxygenase) inhibitor; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; EC 4.1.1.17 (ornithine decarboxylase) inhibitor; ferroptosis inhibitor; geroprotector; hormone antagonist; plant metabolite; prostaglandin antagonist; radical scavenger
chrysin chrysin : A dihydroxyflavone in which the two hydroxy groups are located at positions 5 and 7.	3.4	7	0	7-hydroxyflavonol; dihydroxyflavone	anti-inflammatory agent; antineoplastic agent; antioxidant; EC 2.7.11.18 (myosin-light-chain kinase) inhibitor; hepatoprotective agent; plant metabolite
diosmetin [no description available]	2.6	1	0	3'-hydroxyflavonoid; monomethoxyflavone; trihydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; antioxidant; apoptosis inducer; bone density conservation agent; cardioprotective agent; plant metabolite; tropomyosin-related kinase B receptor agonist; vasodilator agent
diosmin [no description available]	7.72	2	0	dihydroxyflavanone; disaccharide derivative; glycosyloxyflavone; monomethoxyflavone; rutinoside	anti-inflammatory agent; antioxidant
fisetin [no description available]	2.77	3	0	3'-hydroxyflavonoid; 7-hydroxyflavonol; tetrahydroxyflavone	anti-inflammatory agent; antioxidant; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; geroprotector; metabolite; plant metabolite
mangiferin shamimin: isolated from the leaves of Bombax ceiba; structure in first source	2.73	3	0	C-glycosyl compound; xanthones	anti-inflammatory agent; antioxidant; hypoglycemic agent; plant metabolite
3-methylquercetin isorhamnetin : A monomethoxyflavone that is quercetin in which the hydroxy group at position 3' is replaced by a methoxy group.	2.5	2	0	7-hydroxyflavonol; monomethoxyflavone; tetrahydroxyflavone	anticoagulant; EC 1.14.18.1 (tyrosinase) inhibitor; metabolite
morusin morusin: from Morus root bark; structure given in first source. morusin : An extended flavonoid that is flavone substituted by hydroxy groups at positions 5, 2' and 4', a prenyl group at position 3 and a 2,2-dimethyl pyran group across positions 7 and 8.	4.9	1	1	extended flavonoid; trihydroxyflavone	antineoplastic agent; plant metabolite
myricetin [no description available]	2.66	3	0	7-hydroxyflavonol; hexahydroxyflavone	antineoplastic agent; antioxidant; cyclooxygenase 1 inhibitor; food component; geroprotector; hypoglycemic agent; plant metabolite
robinetin robinetin: structure given in first source. robinetin : A pentahydroxyflavone that is flavone substituted by hydroxy groups at positions 3, 7, 3, 4' and 5'.	2.37	2	0	7-hydroxyflavonol; pentahydroxyflavone	plant metabolite
tricetin tricetin : Flavone hydroxylated at positions 3', 4', 5, 5' and 7.	7.11	1	0	pentahydroxyflavone	antineoplastic agent; metabolite
wogonin wogonin: structure in first source. wogonin : A dihydroxy- and monomethoxy-flavone in which the hydroxy groups are positioned at C-5 and C-7 and the methoxy group is at C-8.	2	1	0	dihydroxyflavone; monomethoxyflavone	angiogenesis inhibitor; antineoplastic agent; cyclooxygenase 2 inhibitor; plant metabolite
pterostilbene [no description available]	2.5	2	0	diether; methoxybenzenes; stilbenol	anti-inflammatory agent; antineoplastic agent; antioxidant; apoptosis inducer; hypoglycemic agent; neuroprotective agent; neurotransmitter; plant metabolite; radical scavenger
caffeic acid phenethyl ester phenethyl caffeate : An alkyl caffeate ester in which 2-phenylethyl is the alkyl component.	7.08	1	0	alkyl caffeate ester	anti-inflammatory agent; antibacterial agent; antineoplastic agent; antioxidant; antiviral agent; immunomodulator; metabolite; neuroprotective agent
rosmarinic acid rosmarinic acid: RN given refers to parent cpd; promote OT project. (R)-rosmarinic acid : A stereoisomer of rosmarinic acid having (R)-configuration.. rosmarinic acid : The 1-carboxy-2-(2,4-dihydroxyphenyl)ethyl ester of trans-caffeic acid.	5.17	2	1	rosmarinic acid	geroprotector; plant metabolite
ellagic acid [no description available]	10.33	22	0	catechols; cyclic ketone; lactone; organic heterotetracyclic compound; polyphenol	antioxidant; EC 1.14.18.1 (tyrosinase) inhibitor; EC 2.3.1.5 (arylamine N-acetyltransferase) inhibitor; EC 2.4.1.1 (glycogen phosphorylase) inhibitor; EC 2.5.1.18 (glutathione transferase) inhibitor; EC 2.7.1.127 (inositol-trisphosphate 3-kinase) inhibitor; EC 2.7.1.151 (inositol-polyphosphate multikinase) inhibitor; EC 2.7.4.6 (nucleoside-diphosphate kinase) inhibitor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; EC 5.99.1.2 (DNA topoisomerase) inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; food additive; fungal metabolite; geroprotector; plant metabolite; skin lightening agent
sdz psc 833 valspodar: nonimmunosuppressive cyclosporin analog which is a potent multidrug resistance modifier; 7-10 fold more potent than cyclosporin A; a potent P glycoprotein inhibitor; MW 1215	2.03	1	0	homodetic cyclic peptide
coenzyme q10 coenzyme Q10: Ubiquinone ring with a chain of 10 isoprene units; redox equilibrium with ubiqunol serving in mitochondrial inner membrane to transfer electrons; presence during reconstitution of acetylcholine receptor into phospholipid vesicles yields vesicles active in catalyzing carbamylcholine-sensitive Na+ flux; coenzyme Q10 depletion has been noted with use of statins. coenzyme Q10 : A ubiquinone having a side chain of 10 isoprenoid units. In the naturally occurring isomer, all isoprenyl double bonds are in the E- configuration.	1.97	1	0	ubiquinones	antioxidant; ferroptosis inhibitor; human metabolite
anandamide anandamide : An N-acylethanolamine 20:4 resulting from the formal condensation of carboxy group of arachidonic acid with the amino group of ethanolamine.	2.13	1	0	endocannabinoid; N-acylethanolamine 20:4	human blood serum metabolite; neurotransmitter; vasodilator agent
8-epi-prostaglandin f2alpha 8-epi-prostaglandin F2alpha: a potent preglomerular vasoconstrictor acting principally through thromboxane A2 receptor activation. 8-epi-prostaglandin F2alpha : An isoprostane that is prostaglandin F2alpha having inverted stereochemistry at the 8-position.	3.2	5	0	F2-isoprostane	biomarker; bronchoconstrictor agent; vasoconstrictor agent
4-hydroxyestradiol 4-hydroxyestradiol: catechol estrogen. 4-hydroxy-17beta-estradiol : A 4-hydroxy steroid that consists of 17beta-estradiol having an additional hydroxy group at position 4.	2.46	2	0	4-hydroxy steroid	metabolite
11-ketotestosterone 11-ketotestosterone: RN given refers to cpd without isomeric designation. 11-oxotestosterone : A 3-oxo Delta(4)-steroid that is testosterone carrying an additional oxo substituent at position 11.	2.21	1	0	11-oxo steroid; 17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; androstanoid	androgen; human metabolite; marine xenobiotic metabolite
etretinate retinoid : Oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.	1.96	1	0	enoate ester; ethyl ester; retinoid	keratolytic drug
isotretinoin Isotretinoin: A topical dermatologic agent that is used in the treatment of ACNE VULGARIS and several other skin diseases. The drug has teratogenic and other adverse effects.. isotretinoin : A retinoic acid that is all-trans-retinoic acid in which the double bond which is alpha,beta- to the carboxy group is isomerised to Z configuration. A synthetic retinoid, it is used for the treatment of severe cases of acne and other skin diseases.	2.89	4	0	retinoic acid	antineoplastic agent; keratolytic drug; teratogenic agent
16,16-dimethylprostaglandin e2 16,16-Dimethylprostaglandin E2: A synthetic prostaglandin E analog that protects the gastric mucosa, prevents ulceration, and promotes the healing of peptic ulcers. The protective effect is independent of acid inhibition. It is also a potent inhibitor of pancreatic function and growth of experimental tumors.. 16,16-dimethylprostaglandin E2 : A prostanoid that is prostaglandin E2 in which both of the hydrogens at position 16 have been replaced by methyl groups. A synthetic analogue of prostaglandin E2, it is a potent inhibitor of pancreatic function and growth of experimental tumors. It also protects the gastric mucosa, prevents ulceration, and promotes the healing of peptic ulcers.	1.99	1	0	cyclopentanones; monocarboxylic acid; prostanoid; secondary allylic alcohol	anti-ulcer drug; gastrointestinal drug; radiation protective agent
thromboxane b2 Thromboxane B2: A stable, physiologically active compound formed in vivo from the prostaglandin endoperoxides. It is important in the platelet-release reaction (release of ADP and serotonin).. thromboxane B2 : A member of the class of thromboxanes B that is (5Z,13E)-thromboxa-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15.	2.68	3	0	thromboxanes B	human metabolite; mouse metabolite
2,4-decadienal (2E,4E)-deca-2,4-dienal : A polyunsaturated fatty aldehyde that is decanal which has undergone formal dehydrogenation to introduce trans- double bonds at the 2-3 and 4-5 positions. A product of lipid peroxidation in cell membranes and a component of cooking oil fumes.	2.03	1	0	polyunsaturated fatty aldehyde	apoptosis inducer; nematicide
ubiquinone 8 [no description available]	4.9	1	1	ubiquinones	biomarker
methyl 13-hydroperoxy-9,11-octadecadienoate methyl linoleate hydroperoxide: RN given refers to (Z,Z)-isomer	1.97	1	0
phenylephrine hydrochloride Nose: A part of the upper respiratory tract. It contains the organ of SMELL. The term includes the external nose, the nasal cavity, and the PARANASAL SINUSES.. phenylephrine hydrochloride : A hydrochloride that is the monohydrochloride salt of phenylephrine.	2.37	2	0	hydrochloride
3-amino-1,4-dimethyl-5h-pyrido(4,3-b)indole 3-amino-1,4-dimethyl-5H-pyrido(4,3-b)indole: structure	3.37	7	0	pyridoindole
3-amino-1-methyl-5h-pyrido(4,3-b)indole 3-amino-1-methyl-5H-pyrido(4,3-b)indole: structure	3.23	6	0	pyridoindole
hydroxystilbamidine hydroxystilbamidine: minor descriptor (63-86); on-line & INDEX MEDICUS search STILBAMIDINES (66-86); RN given refers to parent cpd	1.96	1	0
vitamin k 1 Vitamin K 1: A family of phylloquinones that contains a ring of 2-methyl-1,4-naphthoquinone and an isoprenoid side chain. Members of this group of vitamin K 1 have only one double bond on the proximal isoprene unit. Rich sources of vitamin K 1 include green plants, algae, and photosynthetic bacteria. Vitamin K1 has antihemorrhagic and prothrombogenic activity.. phylloquinone : A member of the class of phylloquinones that consists of 1,4-naphthoquinone having methyl and phytyl groups at positions 2 and 3 respectively. The parent of the class of phylloquinones.	3.07	5	0	phylloquinones; vitamin K	cofactor; human metabolite; plant metabolite
sirolimus Sirolimus: A macrolide compound obtained from Streptomyces hygroscopicus that acts by selectively blocking the transcriptional activation of cytokines thereby inhibiting cytokine production. It is bioactive only when bound to IMMUNOPHILINS. Sirolimus is a potent immunosuppressant and possesses both antifungal and antineoplastic properties.. sirolimus : A macrolide lactam isolated from Streptomyces hygroscopicus consisting of a 29-membered ring containing 4 trans double bonds, three of which are conjugated. It is an antibiotic, immunosupressive and antineoplastic agent.	2.51	2	0	antibiotic antifungal drug; cyclic acetal; cyclic ketone; ether; macrolide lactam; organic heterotricyclic compound; secondary alcohol	antibacterial drug; anticoronaviral agent; antineoplastic agent; bacterial metabolite; geroprotector; immunosuppressive agent; mTOR inhibitor
fenretinide Fenretinide: A synthetic retinoid that is used orally as a chemopreventive against prostate cancer and in women at risk of developing contralateral breast cancer. It is also effective as an antineoplastic agent.. 4-hydroxyphenyl retinamide : A retinoid obtained by formal condensation of the carboxy group of all-trans retinoic acid and the anilino group of 4-hydroxyaniline. Synthetic retinoid agonist. Antiproliferative, antioxidant and anticancer agent with a long half-life in vivo. Apoptotic effects appear to be mediated by a mechanism distinct from that of 'classical' retinoids.	1.96	1	0	monocarboxylic acid amide; retinoid	antineoplastic agent; antioxidant
benzphetamine Benzphetamine: A sympathomimetic agent with properties similar to DEXTROAMPHETAMINE. It is used in the treatment of obesity. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1222). benzphetamine : Dextroamphetamine in which the the hydrogens attached to the amino group are substituted by a methyl and a benzyl group. A sympathomimetic agent with properties similar to dextroamphetamine, it is used as its hydrochloride salt in the treatment of obesity.	3.36	7	0	amphetamines; tertiary amine	adrenergic uptake inhibitor; appetite depressant; dopamine uptake inhibitor; sympathomimetic agent
dexmedetomidine [no description available]	2.72	3	0	medetomidine	alpha-adrenergic agonist; analgesic; non-narcotic analgesic; sedative
herbimycin herbimycin: herbicidal antibiotic produced by Streptomyces sp.; see also herbimycin B; structure for herbimycin A in second source. herbimycin : A 19-membered macrocyle incorporating a benzoquinone ring and a lactam functionality. It is an ansamycin antibiotic that induces apoptosis and displays antitumour effects.	2.42	2	0	1,4-benzoquinones; lactam; macrocycle	antimicrobial agent; apoptosis inducer; herbicide; Hsp90 inhibitor; tyrosine kinase inhibitor
lysophosphatidylcholines lysophosphatidylcholine : An acylglycerophosphocholine resulting from partial hydrolysis of a phosphatidylcholine, which removes one of the fatty acyl groups. The structure is depicted in the image where R1 = acyl, R2 = H or where R1 = H, R2 = acyl.	1.98	1	0	1-O-acyl-sn-glycero-3-phosphocholine
cytochalasin b Cytochalasin B: A cytotoxic member of the CYTOCHALASINS.. cytochalasin B : An organic heterotricyclic compound, that is a mycotoxin which is cell permeable an an inhibitor of cytoplasmic division by blocking the formation of contractile microfilaments.	3.39	7	0	cytochalasin; lactam; lactone; organic heterotricyclic compound	actin polymerisation inhibitor; metabolite; mycotoxin; platelet aggregation inhibitor
1,2-oleoylphosphatidylcholine 1,2-oleoylphosphatidylcholine: RN given refers to (Z,Z)-isomer. dioleoyl phosphatidylcholine : A phosphatidylcholine in which the phosphatidyl acyl groups are both oleoyl.	2.1	1	0	phosphatidylcholine(1+)
biliverdine [no description available]	2.73	3	0
cinnamyl alcohol cinnamyl alcohol: RN given refers to parent cpd without isomeric designation. (E)-cinnamyl alcohol : The E (trans) stereoisomer of cinnamyl alcohol.. cinnamyl alcohol : A primary alcohol comprising an allyl core with a hydroxy substituent at the 1-position and a phenyl substituent at the 3-position (geometry of the C=C bond unspecified).	2.06	1	0	cinnamyl alcohol	plant metabolite
ailanthoidol ailanthoidol: from Zanthoxylum ailanthoidos; structure in first source	2.03	1	0
ligustilide ligustilide: found in Umbelliferae plants; RN given refers to cpd without isomeric designation; structure in first source	7.1	1	0	butenolide	metabolite
caryophyllene caryophyllene: RN given refers to cpd without isomeric designation; structure given in first source	2.1	1	0
casein kinase ii Casein Kinase II: A ubiquitous casein kinase that is comprised of two distinct catalytic subunits and dimeric regulatory subunit. Casein kinase II has been shown to phosphorylate a large number of substrates, many of which are proteins involved in the regulation of gene expression.	2.1	1	0
nifuroxazide nifuroxazide: structure	2.03	1	0	benzoic acids
lead Lead: A soft, grayish metal with poisonous salts; atomic number 82, atomic weight 207.2, symbol Pb.	5.65	24	0	carbon group element atom; elemental lead; metal atom	neurotoxin
12-hydroxy-5,8,10,14-eicosatetraenoic acid 12-Hydroxy-5,8,10,14-eicosatetraenoic Acid: A lipoxygenase metabolite of ARACHIDONIC ACID. It is a highly selective ligand used to label mu-opioid receptors in both membranes and tissue sections. The 12-S-HETE analog has been reported to augment tumor cell metastatic potential through activation of protein kinase C. (J Pharmacol Exp Ther 1995; 274(3):1545-51; J Natl Cancer Inst 1994; 86(15):1145-51)	1.99	1	0
2,4,3',5'-tetramethoxystilbene 2,4,3',5'-tetramethoxystilbene: potent inhibitor of human cytochrome P450 1B1; an antihypertensive agent; structure in first source	2.06	1	0
cesium Cesium: A member of the alkali metals. It has an atomic symbol Cs, atomic number 50, and atomic weight 132.91. Cesium has many industrial applications, including the construction of atomic clocks based on its atomic vibrational frequency.	1.96	1	0	alkali metal atom
barium Barium: An element of the alkaline earth group of metals. It has an atomic symbol Ba, atomic number 56, and atomic weight 138. All of its acid-soluble salts are poisonous.	2.02	1	0	alkaline earth metal atom; elemental barium
aluminum Aluminum: A metallic element that has the atomic number 13, atomic symbol Al, and atomic weight 26.98.	5.56	13	0	boron group element atom; elemental aluminium; metal atom
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.	3.06	5	0	morphinane alkaloid
strontium Strontium: An element of the alkaline earth family of metals. It has the atomic symbol Sr, atomic number 38, and atomic weight 87.62.	2.13	1	0	alkaline earth metal atom
bismuth Bismuth: A metallic element that has the atomic symbol Bi, and atomic number 83. Its principal isotope is Bismuth 209.	4.9	1	1	metal atom; pnictogen
arsenic Arsenic: A shiny gray element with atomic symbol As, atomic number 33, and atomic weight 75. It occurs throughout the universe, mostly in the form of metallic arsenides. Most forms are toxic. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), arsenic and certain arsenic compounds have been listed as known carcinogens. (From Merck Index, 11th ed)	6.7	30	0	metalloid atom; pnictogen	micronutrient
indium Indium: A metallic element, atomic number 49, atomic weight 114.818, symbol In. It is named from its blue line in the spectrum.. indium atom : A metallic element first identified and named from the brilliant indigo (Latin indicum) blue line in its flame spectrum.	1.98	1	0	boron group element atom
4-hydroxyaminoquinoline-1-oxide 4-Hydroxyaminoquinoline-1-oxide: A potent mutagen and carcinogen. It is a reduction product of 4-NITROQUINOLINE-1-OXIDE. It binds with nucleic acids and inactivates both bacteria and bacteriophage.	2.38	2	0
gallium Gallium: A rare, metallic element designated by the symbol, Ga, atomic number 31, and atomic weight 69.72.. gallium atom : A metallic element predicted as eka-aluminium by Mendeleev in 1870 and discovered by Paul-Emile Lecoq de Boisbaudran in 1875. Named in honour of France (Latin Gallia) and perhaps also from the Latin gallus cock, a translation of Lecoq.	10.17	3	1	boron group element atom
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.	4.04	4	0	chalcogen; nonmetal atom	macronutrient
methylazoxymethanol acetate Methylazoxymethanol Acetate: The aglycone of CYCASIN. It acts as a potent carcinogen and neurotoxin and inhibits hepatic DNA, RNA, and protein synthesis.	2.65	3	0	azoxy compound
geldanamycin [no description available]	2.06	1	0
musk musk: pure essence from secretion of preputial follicles of Moschus moschiferus L.	2.17	1	0	macrolide
plastoquinone [no description available]	7.08	1	0	plastoquinone
puerarin [no description available]	7.41	1	0	C-glycosyl compound; isoflavonoid
ajoene ajoene: major antiplatelet compound in methanol extract of garlic; also inhibits trypanothione reductase.	1.99	1	0	sulfoxide
enalapril Enalapril: An angiotensin-converting enzyme inhibitor that is used to treat HYPERTENSION and HEART FAILURE.. enalapril : A dicarboxylic acid monoester that is ethyl 4-phenylbutanoate in which a hydrogen alpha to the carboxy group is substituted by the amino group of L-alanyl-L-proline (S-configuration).	2.15	1	0	dicarboxylic acid monoester; dipeptide	antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; geroprotector; prodrug
nitrofurazone Nitrofurazone: A topical anti-infective agent effective against gram-negative and gram-positive bacteria. It is used for superficial WOUNDS AND INJURIES and skin infections. Nitrofurazone has also been administered orally in the treatment of TRYPANOSOMIASIS.. nitrofurazone : A semicarbazone resulting from the formal condensation of semicarbazide with 5-nitrofuraldehyde. A broad spectrum antibacterial drug, although with little activity against Pseudomonas species, it is used as a local application for burns, ulcers, wounds and skin infections.	2.21	1	0
dimyristoylphosphatidylcholine 1,2-di-O-myristoyl-sn-glycero-3-phosphocholine : A 1,2-diacyl-sn-glycero-3-phosphocholine where the two phosphatidyl acyl groups are specified as tetradecanoyl (myristoyl).. dimyristoyl phosphatidylcholine : A phosphatidylcholine where the phosphatidyl acyl groups are specified as tetradecanoyl (myristoyl).	2.66	3	0	1,2-diacyl-sn-glycero-3-phosphocholine; phosphatidylcholine 28:0; tetradecanoate ester	antigen; mouse metabolite
beryllium Beryllium: An element with the atomic symbol Be, atomic number 4, and atomic weight 9.01218. Short exposure to this element can lead to a type of poisoning known as BERYLLIOSIS.. beryllium atom : Alkaline earth metal atom with atomic number 4.	3.5	2	0	alkaline earth metal atom; elemental beryllium; metal allergen	adjuvant; carcinogenic agent; epitope
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.	8.76	11	0	cysteinium	fundamental metabolite
silicon Silicon: A trace element that constitutes about 27.6% of the earth's crust in the form of SILICON DIOXIDE. It does not occur free in nature. Silicon has the atomic symbol Si, atomic number 14, and atomic weight [28.084; 28.086].	2.94	4	0	carbon group element atom; metalloid atom; nonmetal atom
phosphorus Phosphorus: A non-metal element that has the atomic symbol P, atomic number 15, and atomic weight 31. It is an essential element that takes part in a broad variety of biochemical reactions.	5.64	5	1	monoatomic phosphorus; nonmetal atom; pnictogen	macronutrient
boron Boron: A trace element with the atomic symbol B, atomic number 5, and atomic weight [10.806; 10.821]. Boron-10, an isotope of boron, is used as a neutron absorber in BORON NEUTRON CAPTURE THERAPY.	5.36	3	1	boron group element atom; metalloid atom; nonmetal atom	micronutrient
gluconasturtiin gluconasturtiin: hydrolysis yields phenylethyl isothiocyanate; structure in first source. gluconasturtiin : An aralkylglucosinolic acid that consists of 1-thio-beta-D-glucopyranose attached to a 3-phenyl-N-(sulfooxy)propanimidoyl group at the anomeric sulfur.	7.01	1	0	aralkylglucosinolic acid; benzenes
bergamottin bergamottin: constituent of bergamot oil; structure given in first source	2.4	2	0	furanocoumarin	metabolite
apocarotenal apocarotenal: structure. 8'-apo-beta,psi-caroten-8'-al : An apo carotenoid triterpenoid compound arising from oxidative degradation of the beta,beta-carotene skeleton at the 8'-position.	2.03	1	0	apo carotenoid triterpenoid; enal
metaproterenol 1-methoxy-3-indolylmethylglucosinolate: isolated from Moricandia arvensis (Cruciferae); structure given in first source. neoglucobrassicin : An indolyl carbohydrate that is glucobrassicin methoxy substituted at position 1 of the indole moiety.	2.05	1	0
triolein Triolein: (Z)-9-Octadecenoic acid 1,2,3-propanetriyl ester.. triolein : A triglyceride formed by esterification of the three hydroxy groups of glycerol with oleic acid. Triolein is one of the two components of Lorenzo's oil.	2.11	1	0	triglyceride	Caenorhabditis elegans metabolite; plant metabolite
abscisic acid Abscisic Acid: Abscission-accelerating plant growth substance isolated from young cotton fruit, leaves of sycamore, birch, and other plants, and from potatoes, lemons, avocados, and other fruits.. (S)-2-trans-abscisic acid : A 2-trans-abscisic acid with (S)-configuration at the chiral centre.. (+)-abscisic acid : The naturally occurring (1'S)-(+) enantiomer of abscisic acid. It is an important sesquiterpenoid plant hormone which acts as a regulator of plant responses to environmental stresses such as drought and cold.	2.03	1	0	2-trans-abscisic acid
ammonium sulfate Ammonium Sulfate: Sulfuric acid diammonium salt. It is used in CHEMICAL FRACTIONATION of proteins.. ammonium sulfate : An inorganic sulfate salt obtained by reaction of sulfuric acid with two equivalents of ammonia. A high-melting (decomposes above 280degreeC) white solid which is very soluble in water (70.6 g/100 g water at 0degreeC; 103.8 g/100 g water at 100degreeC), it is widely used as a fertilizer for alkaline soils.	2.37	2	0	ammonium salt; inorganic sulfate salt	fertilizer
selenium Selenium: An element with the atomic symbol Se, atomic number 34, and atomic weight 78.97. It is an essential micronutrient for mammals and other animals but is toxic in large amounts. Selenium protects intracellular structures against oxidative damage. It is an essential component of GLUTATHIONE PEROXIDASE.	6.03	22	0	chalcogen; nonmetal atom	micronutrient
triethyllead triethyllead: RN given refers to parent cpd	1.99	1	0
polonium Polonium: A radioactive element that is a member of the chalcogen family. It has the atomic symbol Po, atomic number 84, and the atomic weight of the isotope with the longest half-life (209Po) is 208.98. It decays by alpha-emission.. polonium atom : A radioactive metallic element discovered in 1898 by Marie Sklodowska Curie and named after her home country, Poland (Latin Polonia).	2.37	2	0	chalcogen; metal atom
oxalates Oxalates: Derivatives of OXALIC ACID. Included under this heading are a broad variety of acid forms, salts, esters, and amides that are derived from the ethanedioic acid structure.	1.96	1	0
dizocilpine maleate Dizocilpine Maleate: A potent noncompetitive antagonist of the NMDA receptor (RECEPTORS, N-METHYL-D-ASPARTATE) used mainly as a research tool. The drug has been considered for the wide variety of neurodegenerative conditions or disorders in which NMDA receptors may play an important role. Its use has been primarily limited to animal and tissue experiments because of its psychotropic effects.. dizocilpine maleate : A maleate salt obtained by reaction of dizocilpine with one equivalent of maleic acid.	4.9	1	1	maleate salt; tetracyclic antidepressant	anaesthetic; anticonvulsant; neuroprotective agent; nicotinic antagonist; NMDA receptor antagonist
antimycin a Antimycin A: An antibiotic substance produced by Streptomyces species. It inhibits mitochondrial respiration and may deplete cellular levels of ATP. Antimycin A1 has been used as a fungicide, insecticide, and miticide. (From Merck Index, 12th ed). antimycin A : A nine-membered bis-lactone having methyl substituents at the 2- and 6-positions, an n-hexyl substituent at the 8-position, an acyloxy substituent at the 7-position and an aroylamido substituent at the 3-position. It is produced by Streptomyces bacteria and has found commercial use as a fish poison.	2	1	0	amidobenzoic acid
bongkrekic acid Bongkrekic Acid: An antibiotic produced by Pseudomonas cocovenenans. It is an inhibitor of MITOCHONDRIAL ADP, ATP TRANSLOCASES. Specifically, it blocks adenine nucleotide efflux from mitochondria by enhancing membrane binding.. bongkrekic acid : A tricarboxylic acid that is docosa-2,4,8,10,14,18,20-heptaenedioic acid substituted at positions 2 ,5 and 17 by methyl groups, at positions 6 by a methoxy group and at position 20 by a carboxymethyl group. It is produced by the bacterium Burkholderia gladioli and implicated in outbreaks of food-borne illness involving coconut and corn-based products in Indonesia and China.	2.01	1	0	ether; olefinic compound; tricarboxylic acid	apoptosis inhibitor; ATP/ADP translocase inhibitor; bacterial metabolite; EC 2.5.1.18 (glutathione transferase) inhibitor; toxin
24,25-dihydroxyvitamin d 3 24,25-Dihydroxyvitamin D 3: A physiologically active metabolite of VITAMIN D. The compound is involved in the regulation of calcium metabolism, alkaline phosphatase activity, and enhancing the calcemic effect of CALCITRIOL.	1.96	1	0
1-palmitoyl-2-oleoylphosphatidylcholine 1-palmitoyl-2-oleoylphosphatidylcholine: RN given refers to (Z)-isomer	2.41	2	0
vitamin a2 vitamin A2: RN given refers to cpd without isomeric designation. all-trans-3,4-didehydroretinol : A retinoid derived from 3,4-desaturation of the beta-ionone ring of all-trans-retinol.	2.04	1	0	retinoid; vitamin A	human xenobiotic metabolite; marine xenobiotic metabolite; mouse metabolite
temarotene temarotene: RN given refers to cpd without isomeric designation	1.97	1	0
carboprostacyclin carboprostacyclin: potent stable prostacyclin analog which inhibits platelet aggretation; do not confuse with carboprost (15-methyl-PGF2alpha); RN given refers to (3aS-(2Z,3aalpha,4alpha(1E,R*),5beta,6aalpha))-isomer; structure given in first source	1.98	1	0	prostanoid
involucrin involucrin: soluble precursor protein of cross-linked envelope characteristic of epidermal s. corneum synthesized by keratinocytes in natural & cultured human epithelia; see also related records for prekeratin & stratum corneum basic protein precursor	2.41	2	0
1,2-dioleoyloxy-3-(trimethylammonium)propane 1,2-dioleoyloxy-3-(trimethylammonium)propane: fluorescent probe for phospholipids; RN & structure given in first source	2.59	2	0
(2e,4e,6e,10e)-3,7,11,15-tetramethyl-2,4,6,10,14-hexadecapentaenoic acid (2E,4E,6E,10E)-3,7,11,15-tetramethyl-2,4,6,10,14-hexadecapentaenoic acid: an acyclic retinoid that suppresses hepatocellular carcinoma recurrence; structure in first source	1.96	1	0
tmk 777 [no description available]	2.39	2	0
tmk 688 TMK 688: structure given in first source	2.39	2	0
nuezhenide nuezhenide: from Ligustrum lucidum; structure given in first source; RN refers to trans-isomer	1.98	1	0	saccharolipid
asialo gm1 ganglioside [no description available]	1.98	1	0
3-hydroxyretinol 3-hydroxyretinol: RN given refers to all-trans isomer	2.02	1	0	diol; retinoid
verlukast verlukast: LTD4 receptor antagonist	2.46	2	0
beta-escin [no description available]	3.65	9	0
glucoraphanin glucoraphanin: precursor of sulforaphane. glucoraphanin : A thia-glucosinolic acid that is glucoerucin in which the sulfur atom of the methyl thioether group has been oxidised to the corresponding sulfoxide.	2.05	1	0	sulfoxide; thia-alkylglucosinolic acid
nitrofurantoin Nitrofurantoin: A urinary anti-infective agent effective against most gram-positive and gram-negative organisms. Although sulfonamides and antibiotics are usually the agents of choice for urinary tract infections, nitrofurantoin is widely used for prophylaxis and long-term suppression.. nitrofurantoin : An imidazolidine-2,4-dione that is hydantoin substituted at position 1 by a [(5-nitro-2-furyl)methylene]amino group. An antibiotic that damages bacterial DNA.	4	4	0	imidazolidine-2,4-dione; nitrofuran antibiotic; organonitrogen heterocyclic antibiotic; organooxygen heterocyclic antibiotic	antibacterial drug; antiinfective agent; hepatotoxic agent
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.	1.99	1	0	cyclic ether; enol; polyunsaturated fatty acid; very long-chain fatty acid	calcium ionophore; metabolite
artesunate artesunic acid: RN given for (3R-(3alpha,5abeta,6beta,8abeta,9alpha,10alpha,12beta,(2aR*))-isomer; succinic ester of artemether	2.11	1	0	artemisinin derivative; cyclic acetal; dicarboxylic acid monoester; hemisuccinate; semisynthetic derivative; sesquiterpenoid	antimalarial; antineoplastic agent; ferroptosis inducer
isoborneol isoborneol: RN given refers to cpd without isomeric designation; structure	2.43	2	0	borneol
eupatorin-5-methyl ether eupatorin-5-methyl ether: has antineoplastic activity; structure in first source	2.1	1	0
staurosporine staurosporinium : Conjugate acid of staurosporine.	2.69	3	0	ammonium ion derivative
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.	2	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.	1.99	1	0	L-alpha-amino acid zwitterion; S-hydrocarbyl-L-cysteine	antineoplastic agent; metabolite
s-allylmercaptocysteine S-allylmercaptocysteine: a potent inhibitor of cell proliferation	7.13	1	0
valyl-prolyl-proline Val-Pro-Pro : A tripeptide composed of L-valine and two L-proline units joined by peptide linkages.	2.02	1	0	tripeptide	metabolite
sincalide Sincalide: An octapeptide hormone present in the intestine and brain. When secreted from the gastric mucosa, it stimulates the release of bile from the gallbladder and digestive enzymes from the pancreas.	2.41	1	0	oligopeptide
ginsenoside m1 ginsenoside M1: structure in first source. ginsenoside C-K : A ginsenoside found in Panax species that is dammarane which is substituted by hydroxy groups at the 3beta, 12beta and 20 pro-S positions, in which the hydroxy group at position 20 has been converted to the corresponding beta-D-glucopyranoside, and in which a double bond has been introduced at the 24-25 position.	2.25	1	0	12beta-hydroxy steroid; 3beta-hydroxy-4,4-dimethylsteroid; 3beta-hydroxy steroid; beta-D-glucoside; ginsenoside; tetracyclic triterpenoid	anti-allergic agent; anti-inflammatory agent; antineoplastic agent; hepatoprotective agent; plant metabolite
nu 7026 2-(morpholin-4-yl)benzo(h)chromen-4-one: a radiosensitizing agent that inhibits DNA-dependent protein kinase; structure in first source	2.11	1	0	organic heterotricyclic compound; organooxygen compound
mocetinostat mocetinostat: undergoing phase II clinical trials for treatment of cancer. mocetinostat : A benzamide obtained by formal condensation of the carboxy group of 4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzoic acid with one of the amino groups of benzene-1,2-diamine. It is an orally active and isotype-selective HDAC inhibitor which exhibits antitumour activity (IC50 = 0.15, 0.29, 1.66 and 0.59 muM for HDAC1, HDAC2, HDAC3 and HDAC11).	3.62	9	0	aminopyrimidine; benzamides; pyridines; secondary amino compound; secondary carboxamide; substituted aniline	antineoplastic agent; apoptosis inducer; autophagy inducer; cardioprotective agent; EC 3.5.1.98 (histone deacetylase) inhibitor; hepatotoxic agent
lipid a Lipid A: Lipid A is the biologically active component of lipopolysaccharides. It shows strong endotoxic activity and exhibits immunogenic properties.. lipid A : The glycolipid moiety of bacterial lipopolysaccharide (R can be either hydrogen or a fatty acyl group).	4.9	1	1	dodecanoate ester; lipid A; tetradecanoate ester	Escherichia coli metabolite
thiocolchicoside thiocolchicoside: used in combination with glafenine and meprobamate to tranquilize patients undergoing hysterosalpingography; structure	4.9	1	1	glycoside
secoisolariciresinol diglucoside secoisolariciresinol diglucoside: major precursor of mammalian lignans; structure given in first source; RN given refers to B-D-GLUCO isomer	2.41	1	0
ginsenoside rg3 ginsenoside Rg3: from Red ginseng; inhibits lung metastasis of tumor cells; structure given in first source. (20S)-ginsenoside Rg3 : A ginsenoside found in Panax ginseng and Panax japonicus var. major that is dammarane which is substituted by hydroxy groups at the 3beta, 12beta and 20 pro-S positions, in which the hydroxy group at position 3 has been converted to the corresponding beta-D-glucopyranosyl-beta-D-glucopyranoside, and in which a double bond has been introduced at the 24-25 position.	7.57	2	0	ginsenoside; glycoside; tetracyclic triterpenoid	angiogenesis modulating agent; antineoplastic agent; apoptosis inducer; plant metabolite
sorbitan monooleate [no description available]	2.15	1	0	fatty acid ester
rucaparib AG14447: Poly(ADP-ribose) polymerase inhibitor; structure in first source	4.9	1	1	azepinoindole; caprolactams; organofluorine compound; secondary amino compound	antineoplastic agent; EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor
zeolites [no description available]	2.49	2	0
isoleucyl-prolyl-proline [no description available]	2.02	1	0	oligopeptide
g(m1) ganglioside G(M1) Ganglioside: A specific monosialoganglioside that accumulates abnormally within the nervous system due to a deficiency of GM1-b-galactosidase, resulting in GM1 gangliosidosis.. ganglioside GM1 : A sialotetraosylceramide consisting of a branched pentasaccharide made up from one sialyl residue, two galactose residues, one N-acetylgalactosamine residue and a glucose residue at the reducing end attached to N-stearoylsphingosine via a beta-linkage.	2.4	2	0	alpha-N-acetylneuraminosyl-(2->3)-[beta-D-galactosyl-(1->3)-N-acetyl-beta-D-galactosaminyl-(1->4)]-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1')-N-acylsphingosine; sialotetraosylceramide
aluminum oxide Aluminum Oxide: An oxide of aluminum, occurring in nature as various minerals such as bauxite, corundum, etc. It is used as an adsorbent, desiccating agent, and catalyst, and in the manufacture of dental cements and refractories.	3.11	5	0
3'-methoxy-4'-nitroflavone 3'-methoxy-4'-nitroflavone: structure given in first source	2.41	2	0
artenimol artenimol: derivative of antimalarial drug artemisinin (quinghaosu)	4.9	1	1
trans-sodium crocetinate trans-sodium crocetinate: vitamin A-analog that increases diffusivity of oxygen in aqueous solutions, including plasma	2.71	3	0
alpha-synuclein alpha-Synuclein: A synuclein that is a major component of LEWY BODIES and plays a role in SYNUCLEINOPATHIES, neurodegeneration and neuroprotection.	7.69	2	0
oxadiazoles Oxadiazoles: Compounds containing five-membered heteroaromatic rings containing two carbons, two nitrogens, and one oxygen atom which exist in various regioisomeric forms.	4.9	1	1
lactulose Lactulose: A synthetic disaccharide used in the treatment of constipation and hepatic encephalopathy. It has also been used in the diagnosis of gastrointestinal disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p887). lactulose : A synthetic galactosylfructose disaccharide used in the treatment of constipation and hepatic encephalopathy.	4.9	1	1
acetyl-11-ketoboswellic acid acetyl-11-ketoboswellic acid: a 5-lipoxygenase inhibitor; structure given in first source	2.21	1	0	triterpenoid
nystatin a1 Nystatin: Macrolide antifungal antibiotic complex produced by Streptomyces noursei, S. aureus, and other Streptomyces species. The biologically active components of the complex are nystatin A1, A2, and A3.. nystatin : A heterogeneous mixture of polyene compounds produced by cultures of Streptomyces noursei. It mainly consists of three biologically active components designated nystatin A1, nystatin A2, and nystatin A3. It is used to treat oral and dermal fungal infections.. nystatin A1 : A polyene macrolide antibiotic; part of the nystatin complex produced by several Streptomyces species. It is an antifungal antibiotic used for the treatment of topical fungal infections caused by a broad spectrum of fungal pathogens comprising yeast-like and filamentous species.	2.13	1	0	nystatins
linoleic acid hydroperoxide linoleic acid hydroperoxide: RN refers to (Z,Z)-isomer. linoleic acid hydroperoxide : A HPODE that is a mono-hydroperoxy derivative of linoleic acid	1.97	1	0
chlorophyll b [no description available]	1.96	1	0	chlorophyll	cofactor
losartan potassium Erythropoietin: Glycoprotein hormone, secreted chiefly by the KIDNEY in the adult and the LIVER in the FETUS, that acts on erythroid stem cells of the BONE MARROW to stimulate proliferation and differentiation.	1.98	1	0
corannulene corannulene: structure in first source	2.25	1	0
dextrothyroxine [no description available]	2.05	1	0
s-tetradecanoyl-coenzyme a myristoyl-CoA : A long-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of myristic acid.	2.06	1	0	11,12-saturated fatty acyl-CoA; long-chain fatty acyl-CoA	Escherichia coli metabolite; mouse metabolite
sepharose agarose : A linear polysaccharide made up from alternating D-galactose and 3,6-anhydro-alpha-L-galactopyranose residues joined by alpha-(1->3)- and beta-(1->4)-linkages.	2.73	3	0
pituitrin Pituitrin: A substance or extract from the neurohypophysis (PITUITARY GLAND, POSTERIOR).	2.01	1	0
glycoursodeoxycholic acid glycoursodeoxycholic acid : A bile acid glycine conjugate derived from ursoodeoxycholic acid.. glycoursodeoxycholate : A N-acylglycinate that is the conjugate base of glycoursodeoxycholic acid. obtained by deprotonation of the carboxy group; major species at pH 7.3.	2	1	0	bile acid glycine conjugate; N-acylglycine	human blood serum metabolite; neuroprotective agent
nomilin [no description available]	1.97	1	0
clove Madagascar: One of the Indian Ocean Islands off the southeast coast of Africa. Its capital is Antananarivo. It was formerly called the Malagasy Republic. Discovered by the Portuguese in 1500, its history has been tied predominantly to the French, becoming a French protectorate in 1882, a French colony in 1896, and a territory within the French union in 1946. The Malagasy Republic was established in the French Community in 1958 but it achieved independence in 1960. Its name was changed to Madagascar in 1975. (From Webster's New Geographical Dictionary, 1988, p714)	2.03	1	0
acid phosphatase Acid Phosphatase: An enzyme that catalyzes the conversion of an orthophosphoric monoester and water to an alcohol and orthophosphate. EC 3.1.3.2.	3.07	5	0
erythrosine Erythrosine: A tetraiodofluorescein used as a red coloring in some foods (cherries, fish), as a disclosure of DENTAL PLAQUE, and as a stain of some cell types. It has structural similarity to THYROXINE.. erythrosin B : An organic sodium salt that is the disodium salt of 2-(2,4,5,7-tetraiodo-6-oxido-3-oxo-8a,10a-dihydroxanthen-9-yl)benzoic acid.	1.97	1	0
nodularin nodularin: cyclic pentapeptide toxin from NODULARIA SPUMIGENA	2.1	1	0	ether
diphenylmethyl selenocyanate diphenylmethyl selenocyanate: an anticarcinogenenic agent; structure in first source	2.03	1	0
aflatoxin m1 Aflatoxin M1: A 4-hydroxylated metabolite of AFLATOXIN B1, one of the MYCOTOXINS from ASPERGILLUS tainted food. It is associated with LIVER damage and cancer resulting from its P450 activation to the epoxide which alkylates DNA. Toxicity depends on the balance of liver enzymes that activate it (CYTOCHROME P-450) and others that detoxify it (GLUTATHIONE S TRANSFERASE) (Pharmac Ther 50.443 1991). Primates & rat are sensitive while mouse and hamster are tolerant (Canc Res 29.236 1969).. aflatoxin M1 : A member of the class of aflatoxins that is aflatoxin B1 in which the hydrogen at position 9a is replaced by a hydroxy group.	1.96	1	0	aflatoxin; aromatic ether; aromatic ketone; tertiary alcohol	Aspergillus metabolite; human xenobiotic metabolite; mammalian metabolite
cyanidin-3-o-beta-glucopyranoside cyanidin-3-O-beta-glucopyranoside: a natural compound distributed in several fruits & vegetables, such as strawberry, rhubarb, cherry, red cabbage, red onion, cranberries, etc.	2.15	1	0
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	6.78	11	1	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
cytochrome c-t Cytochromes c: Cytochromes of the c type that are found in eukaryotic MITOCHONDRIA. They serve as redox intermediates that accept electrons from MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX III and transfer them to MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX IV.	3.46	7	0
melitten Melitten: Basic polypeptide from the venom of the honey bee (Apis mellifera). It contains 26 amino acids, has cytolytic properties, causes contracture of muscle, releases histamine, and disrupts surface tension, probably due to lysis of cell and mitochondrial membranes.	1.96	1	0
ceruletide Ceruletide: A specific decapeptide obtained from the skin of Hila caerulea, an Australian amphibian. Caerulein is similar in action and composition to CHOLECYSTOKININ. It stimulates gastric, biliary, and pancreatic secretion; and certain smooth muscle. It is used in paralytic ileus and as diagnostic aid in pancreatic malfunction.. ceruletide : A decapeptide comprising 5-oxoprolyl, glutamyl, aspartyl, O-sulfotyrosyl, threonyl, glycyl, tryptopyl, methionyl, aspartyl and phenylalaninamide residues in sequence. Found in the skins of certain Australian amphibians, it is an analogue of the gastrointestinal peptide hormone cholecystokinin and stimulates gastric, biliary, and pancreatic secretion. It is used in cases of paralysis of the intestine (paralytic ileus) and as a diagnostic aid in pancreatic malfunction.	2.13	1	0	oligopeptide	diagnostic agent; gastrointestinal drug
atrial natriuretic factor Atrial Natriuretic Factor: A potent natriuretic and vasodilatory peptide or mixture of different-sized low molecular weight PEPTIDES derived from a common precursor and secreted mainly by the HEART ATRIUM. All these peptides share a sequence of about 20 AMINO ACIDS.	1.99	1	0	polypeptide
glucagon Glucagon: A 29-amino acid pancreatic peptide derived from proglucagon which is also the precursor of intestinal GLUCAGON-LIKE PEPTIDES. Glucagon is secreted by PANCREATIC ALPHA CELLS and plays an important role in regulation of BLOOD GLUCOSE concentration, ketone metabolism, and several other biochemical and physiological processes. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1511). glucagon : A 29-amino acid peptide hormone consisting of His, Ser, Gln, Gly, Thr, Phe, Thr, Ser, Asp, Tyr, Ser, Lys, Tyr, Leu, Asp, Ser, Arg, Arg, Ala, Gln, Asp, Phe, Val, Gln, Trp, Leu, Met, Asn and Thr residues joined in sequence.	1.96	1	0	peptide hormone
neuropeptide y Neuropeptide Y: A 36-amino acid peptide present in many organs and in many sympathetic noradrenergic neurons. It has vasoconstrictor and natriuretic activity and regulates local blood flow, glandular secretion, and smooth muscle activity. The peptide also stimulates feeding and drinking behavior and influences secretion of pituitary hormones.	2.15	1	0
tannins Tannins: Polyphenolic compounds with molecular weights of around 500-3000 daltons and containing enough hydroxyl groups (1-2 per 100 MW) for effective cross linking of other compounds (ASTRINGENTS). The two main types are HYDROLYZABLE TANNINS and CONDENSED TANNINS. Historically, the term has applied to many compounds and plant extracts able to render skin COLLAGEN impervious to degradation. The word tannin derives from the Celtic word for OAK TREE which was used for leather processing.	4.59	8	0
oligonucleotides [no description available]	4.37	20	0
glucagon-like peptide 1 Glucagon-Like Peptide 1: A peptide of 36 or 37 amino acids that is derived from PROGLUCAGON and mainly produced by the INTESTINAL L CELLS. GLP-1(1-37 or 1-36) is further N-terminally truncated resulting in GLP-1(7-37) or GLP-1-(7-36) which can be amidated. These GLP-1 peptides are known to enhance glucose-dependent INSULIN release, suppress GLUCAGON release and gastric emptying, lower BLOOD GLUCOSE, and reduce food intake.	2.05	1	0
cellulose DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.	11.01	8	1	glycoside
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	3.86	12	0	1,2-diacyl-sn-glycero-3-phosphocholine
(9R)-9-chloro-11,17-dihydroxy-17-(2-hydroxy-1-oxoethyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one Beclomethasone: An anti-inflammatory, synthetic glucocorticoid. It is used topically as an anti-inflammatory agent and in aerosol form for the treatment of ASTHMA.. beclomethasone : A 17alpha-hydroxy steroid that is prednisolone in which the hydrogens at the 9alpha and 16beta positions are substituted by a chlorine and a methyl group, respectively.	2.92	1	0	21-hydroxy steroid
chlorophyll a Chlorophyll: Porphyrin derivatives containing magnesium that act to convert light energy in photosynthetic organisms.. chlorophyll : A family of magnesium porphyrins, defined by the presence of a fifth ring beyond the four pyrrole-like rings. The rings can have various side chains which usually include a long phytol chain.	3.63	9	0	chlorophyll; methyl ester	cofactor
bis(tri-n-butyltin)oxide bis(tri-n-butyltin)oxide: RN given refers to parent cpd; RN in Chemline for tributylin: 688-73-3	7.71	3	0	inorganic molecular entity
vendex Torque: The rotational force about an axis that is equal to the product of a force times the distance from the axis where the force is applied.	2.02	1	0	organotin acaricide
3-(3-(4-((pyridin-2-yloxy)methyl)benzyl)isoxazol-5-yl)pyridin-2-amine APX001A: has antifungal activity; structure in first source	4.9	1	1
hoe 33342 bisbenzimide ethoxide trihydrochloride: benzimidazole fluorescent dye	2.04	1	0
ubiquinone Ubiquinone: A lipid-soluble benzoquinone which is involved in ELECTRON TRANSPORT in mitochondrial preparations. The compound occurs in the majority of aerobic organisms, from bacteria to higher plants and animals.	5.71	3	1
lucifer yellow lucifer yellow: RN given refers to di-Li salt	1.97	1	0	organic lithium salt	fluorochrome
chitosan [no description available]	2.21	1	0
bucladesine Bucladesine: A cyclic nucleotide derivative that mimics the action of endogenous CYCLIC AMP and is capable of permeating the cell membrane. It has vasodilator properties and is used as a cardiac stimulant. (From Merck Index, 11th ed). bucladesine : A 3',5'-cyclic purine nucleotide that is the 2'-butanoate ester and 6-N-butanoyl derivative of 3',5'-cyclic AMP.	2.66	3	0	3',5'-cyclic purine nucleotide
sodium hypochlorite Sodium Hypochlorite: It is used as an oxidizing and bleaching agent and as a disinfectant. (From Grant & Hackh's Chemical Dictionary, 5th ed). sodium hypochlorite : An inorganic sodium salt in which hypochlorite is the counterion. It is used as a bleaching and disinfecting agent and is commonly found in household bleach.	1.98	1	0	inorganic sodium salt	bleaching agent; disinfectant
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.	2.68	3	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.	2.38	2	0	inorganic sodium salt; nitrite salt	antidote to cyanide poisoning; antihypertensive agent; antimicrobial food preservative; food antioxidant; poison
s-adenosylmethionine (R)-S-adenosyl-L-methionine : An S-adenosyl-L-methionine that has R-configuration.. S-adenosyl-L-methionine zwitterion : A zwitterionic tautomer of S-adenosyl-L-methionine arising from shift of the proton from the carboxy group to the amino group.. (R)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has R-configuration; major species at pH 7.3.. (S)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has S-configuration; major species at pH 7.3.. S-adenosyl-L-methionine : A sulfonium compound that is the S-adenosyl derivative of L-methionine. It is an intermediate in the metabolic pathway of methionine.	1.96	1	0	organic cation; sulfonium compound	coenzyme; cofactor; human metabolite; micronutrient; Mycoplasma genitalium metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
gdc 0449 HhAntag691: inhibits the hedgehog pathway and ABC transporters; has antineoplastic activity	2.41	1	0	benzamides; monochlorobenzenes; pyridines; sulfone	antineoplastic agent; Hedgehog signaling pathway inhibitor; SMO receptor antagonist; teratogenic agent
arabinogalactan [no description available]	8.07	3	0
mk 2206 MK 2206: a protein kinase inhibitor and antineoplastic agent	2.1	1	0	organic heterotricyclic compound	EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor
trelstar Triptorelin Pamoate: A potent synthetic long-acting agonist of GONADOTROPIN-RELEASING HORMONE with D-tryptophan substitution at residue 6.	1.98	1	0
mannans [no description available]	4.9	1	1
bms-790052 daclatasvir: an HCV NS5A inhibitor. daclatasvir : A member of the class of biphenyls that is a potent inhibitor of nonstructural protein 5A and is used (as its hydrochloride salt) for treatment of hepatitis C.	2.11	1	0	biphenyls; carbamate ester; carboxamide; imidazoles; valine derivative	antiviral drug; nonstructural protein 5A inhibitor
glycolipids [no description available]	2.55	2	0
piperidines Piperidines: A family of hexahydropyridines.	4.27	18	0
resolvin d1 resolvin D1: an anti-inflammatory lipid mediator; structure in first source. resolvin D1 : A resolvin that is docosa-4Z,9E,11E,13Z,15E,19Z-hexaenoic acid which is substituted by hydroxy groups at the 7, 8, and 17 positions (the 7S,8R,17S-stereoisomer).	7.13	1	0	hydroxy polyunsaturated fatty acid; resolvin; triol	anti-inflammatory agent
thymosin Thymosin: Thymosin. A family of heat-stable, polypeptide hormones secreted by the thymus gland. Their biological activities include lymphocytopoiesis, restoration of immunological competence and enhancement of expression of T-cell characteristics and function. They have therapeutic potential in patients having primary or secondary immunodeficiency diseases, cancer or diseases related to aging.	1.97	1	0
interleukin-8 Interleukin-8: A member of the CXC chemokine family that plays a role in the regulation of the acute inflammatory response. It is secreted by variety of cell types and induces CHEMOTAXIS of NEUTROPHILS and other inflammatory cells.	4.12	14	0
hamamelitannin hamamelitannin: cytotoxic from witch hazel (Hamamelis virginiana); structure in first source	2.01	1	0	gallate ester
punicalagin punicalagin: hepatoprotective agent isolated from Terminalia catappa; structure in first source	2.49	2	0	tannin
isoquercitrin [no description available]	2.01	1	0
coronarin d coronarin D: from Hedychium coronarium; inhibits both constitutive and inducible nuclear factor-kappa B pathway activation, leading to potentiation of apoptosis, inhibition of invasion, and suppression of osteoclastogenesis; structure in first source	7.6	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.	4.08	15	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.	12.43	37	1	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
novobiocin Novobiocin: An antibiotic compound derived from Streptomyces niveus. It has a chemical structure similar to coumarin. Novobiocin binds to DNA gyrase, and blocks adenosine triphosphatase (ATPase) activity. (From Reynolds, Martindale The Extra Pharmacopoeia, 30th ed, p189). novobiocin : A coumarin-derived antibiotic obtained from Streptomyces niveus.	2.9	4	0	carbamate ester; ether; hexoside; hydroxycoumarin; monocarboxylic acid amide; monosaccharide derivative; phenols	antibacterial agent; antimicrobial agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; Escherichia coli metabolite; hepatoprotective agent
tetracycline Tetracycline: A naphthacene antibiotic that inhibits AMINO ACYL TRNA binding during protein synthesis.. tetracycline : A broad-spectrum polyketide antibiotic produced by the Streptomyces genus of actinobacteria.	4.9	1	1
oxytetracycline, anhydrous Oxytetracycline: A TETRACYCLINE analog isolated from the actinomycete STREPTOMYCES RIMOSUS and used in a wide variety of clinical conditions.. oxytetracycline : A tetracycline used for treatment of infections caused by a variety of Gram positive and Gram negative microorganisms including Mycoplasma pneumoniae, Pasteurella pestis, Escherichia coli, Haemophilus influenzae (respiratory infections), and Diplococcus pneumoniae.	2.13	1	0
salicylates Salicylates: The salts or esters of salicylic acids, or salicylate esters of an organic acid. Some of these have analgesic, antipyretic, and anti-inflammatory activities by inhibiting prostaglandin synthesis.. hydroxybenzoate : Any benzoate derivative carrying a single carboxylate group and at least one hydroxy substituent.. salicylates : Any salt or ester arising from reaction of the carboxy group of salicylic acid, or any ester resulting from the condensation of the phenolic hydroxy group of salicylic acid with an organic acid.. salicylate : A monohydroxybenzoate that is the conjugate base of salicylic acid.	2.9	4	0	monohydroxybenzoate	plant metabolite
dicumarol Dicumarol: An oral anticoagulant that interferes with the metabolism of vitamin K. It is also used in biochemical experiments as an inhibitor of reductases.	2.88	4	0	hydroxycoumarin	anticoagulant; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; Hsp90 inhibitor; vitamin K antagonist
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.	4.82	33	0	benzenes; hydroxycoumarin; methyl ketone
ferulenol ferulenol: intoxicating component of powdered Ferula communis variety brevifolia; RN given for (E,E)-isomer	2.15	1	0
6-o-palmitoylascorbic acid [no description available]	2.04	1	0	fatty acid ester
citrinin Citrinin: Antibiotic and mycotoxin from Aspergillus niveus and Penicillium citrinum.	2	1	0
teriflunomide [no description available]	4.9	1	1	(trifluoromethyl)benzenes; aromatic amide; enamide; enol; nitrile; secondary carboxamide	drug metabolite; EC 1.3.98.1 [dihydroorotate oxidase (fumarate)] inhibitor; hepatotoxic agent; non-steroidal anti-inflammatory drug; tyrosine kinase inhibitor
epidermal growth factor Epidermal Growth Factor: A 6-kDa polypeptide growth factor initially discovered in mouse submaxillary glands. Human epidermal growth factor was originally isolated from urine based on its ability to inhibit gastric secretion and called urogastrone. Epidermal growth factor exerts a wide variety of biological effects including the promotion of proliferation and differentiation of mesenchymal and EPITHELIAL CELLS. It is synthesized as a transmembrane protein which can be cleaved to release a soluble active form.	3.37	7	0
kaolinite Kaolin: The most common mineral of a group of hydrated aluminum silicates, approximately H2Al2Si2O8-H2O. It is prepared for pharmaceutical and medicinal purposes by levigating with water to remove sand, etc. (From Merck Index, 11th ed) The name is derived from Kao-ling (Chinese: high ridge), the original site. (From Grant & Hackh's Chemical Dictionary, 5th ed). kaolin : An aluminosilicate soft white mineral named after the hill in China (Kao-ling) from which it was mined for centuries. In its natural state kaolin is a white, soft powder consisting principally of the mineral kaolinite, and varying amounts of other minerals such as muscovite, quartz, feldspar, and anatase. It is used in the manufacture of china and porcelain and also widely used in the production of paper, rubber, paint, drying agents, and many other products.	2.77	3	0	aluminosilicate mineral; mixture	antidiarrhoeal drug; excipient
clay Clay: A naturally-occurring rock or soil constituent characterized by particles with a diameter of less than 0.005 mm. It is composed primarily of hydrous aluminum silicates, trace amounts of metal OXIDES, and organic matter.	2.99	4	0
bismuth oxybromide bismuth oxybromide: bismuth oxybromide (BiOBr) nanoplate microspheres were used to remove NO in indoor air under visible light irradiation	4.9	1	1
transforming growth factor beta Transforming Growth Factor beta: A factor synthesized in a wide variety of tissues. It acts synergistically with TGF-alpha in inducing phenotypic transformation and can also act as a negative autocrine growth factor. TGF-beta has a potential role in embryonal development, cellular differentiation, hormone secretion, and immune function. TGF-beta is found mostly as homodimer forms of separate gene products TGF-beta1, TGF-beta2 or TGF-beta3. Heterodimers composed of TGF-beta1 and 2 (TGF-beta1.2) or of TGF-beta2 and 3 (TGF-beta2.3) have been isolated. The TGF-beta proteins are synthesized as precursor proteins.	3.71	10	0
phytoestrogens Phytoestrogens: Compounds derived from plants, primarily ISOFLAVONES that mimic or modulate endogenous estrogens, usually by binding to ESTROGEN RECEPTORS.	4.9	1	1
okadaic acid Okadaic Acid: A specific inhibitor of phosphoserine/threonine protein phosphatase 1 and 2a. It is also a potent tumor promoter. It is produced by DINOFLAGELLATES and causes diarrhetic SHELLFISH POISONING.. okadaic acid : A polycyclic ether that is produced by several species of dinoflagellates, and is known to accumulate in both marine sponges and shellfish. A polyketide, polyether derivative of a C38 fatty acid, it is one of the primary causes of diarrhetic shellfish poisoning (DSP). It is a potent inhibitor of specific protein phosphatases and is known to have a variety of negative effects on cells.	7.41	2	0	ketal
pyrethrins [no description available]	2.47	2	0
kiss1 protein, human Kisspeptins: Intercellular signaling peptides that were originally characterized by their ability to suppress NEOPLASM METASTASIS. Kisspeptins have since been found to play an important role in the neuroendocrine regulation of REPRODUCTION.	2.6	1	0
agar Agar: A complex sulfated polymer of galactose units, extracted from Gelidium cartilagineum, Gracilaria confervoides, and related red algae. It is used as a gel in the preparation of solid culture media for microorganisms, as a bulk laxative, in making emulsions, and as a supporting medium for immunodiffusion and immunoelectrophoresis.. agar : A complex mixture of polysaccharides extracted from species of red algae. Its two main components are agarose and agaropectin. Agarose is the component responsible for the high-strength gelling properties of agar, while agaropectin provides the viscous properties.	2.65	3	0
hirudin Hirudin: A 65-residue polypeptide from LEECHES.	4.9	1	1
cyclin d1 Cyclin D1: Protein encoded by the bcl-1 gene which plays a critical role in regulating the cell cycle. Overexpression of cyclin D1 is the result of bcl-1 rearrangement, a t(11;14) translocation, and is implicated in various neoplasms.	4.34	19	0
caseins Caseins: A mixture of related phosphoproteins occurring in milk and cheese. The group is characterized as one of the most nutritive milk proteins, containing all of the common amino acids and rich in the essential ones.	3.09	5	0
thearubigin thearubigin: from black tea leaves; a catechin oxidized product; a mixture of heterogenous polyphenols	2.41	2	0
asbestos, crocidolite Asbestos, Crocidolite: A lavender, acid-resistant asbestos.	5.44	15	1
phthalocyanine phthalocyanine : A tetrapyrrole fundamental parent that consists of four isoindole-type units, with the connecting carbon atoms in the macrocycle replaced by nitrogen.	1.96	1	0	phthalocyanines; tetrapyrrole fundamental parent
nitrophenols Nitrophenols: PHENOLS carrying nitro group substituents.	4.15	6	0
bassianolide bassianolide: cyclodepsipeptide from mycelia of Beauveria bassiana; inhibits isotonic contractions induced by acetylcholine. bassianolide : A cyclodepsipeptide consisting of a cyclic tetramer of the depsipeptide D-Hiv-N-methyl-L-leucine (where D-Hiv = D-alpha-hydroxyisovaleric acid). Found in the fungal species Beauveria bassiana and Verticillium lecanii, it has insecticidal properties and is used as a commercial biopesticide to control of insects of agricultural, veterinary and medical significance. For elucidation of the structure, see Suzuki et al., Tetrahedron Lett. 1977 v25, 2167-2170.	4.02	14	0	cyclodepsipeptide; cyclooctadepsipeptide	antineoplastic agent; fungal metabolite; insecticide
angiotensin i Angiotensin I: A decapeptide that is cleaved from precursor angiotensinogen by RENIN. Angiotensin I has limited biological activity. It is converted to angiotensin II, a potent vasoconstrictor, after the removal of two amino acids at the C-terminal by ANGIOTENSIN CONVERTING ENZYME.. angiotensin I : A ten amino acid peptide formed by renin cleavage of angiotensinogen. Angiotensin I has no direct biological function except that high levels can stimulate catecholamine production. It is metabolized to its biologically active byproduct angiotensin II, a potent vasoconstrictor, by angiotensin converting enzyme (ACE) through cleavage of the two terminal amino acids.. angiotensin I dizwitterion : A peptide zwitterion that is the dizwitterionic form of angiotensin I having both carboxy groups deprotonated and the aspartyl amino group and arginine side-chain protonated. It is the major species at pH 7.3.	3.5	2	0	angiotensin; peptide zwitterion	human metabolite; neurotransmitter agent
plutonium dioxide plutonium dioxide: RN given refers to cpd with MF of Pu-O2	1.96	1	0
gibberellins [no description available]	2.03	1	0
copper bis(3,5-diisopropylsalicylate) copper bis(3,5-diisopropylsalicylate): copper is intricate part of molecule; not copper salt; RN given refers to cpd with specified locants for methylethyl moieties	2.66	3	0
aldrin Aldrin: A highly poisonous substance that was formerly used as an insecticide. The manufacture and use has been discontinued in the U.S. (From Merck Index, 11th ed). aldrin : An organochlorine compound resulting from the Diels-Alder reaction of hexachlorocyclopentadiene with norbornadiene. A proinsecticide (by epoxidation of the non-chlorinated double bond to give dieldrin), it was widely used as an insecticide before being banned in the 1970s as a persistent organic pollutant.	9.16	5	0
peoniflorin peoniflorin: from Radix and of Paeonia suffruticosa	2.41	1	0
aldrin-transdiol aldrin-transdiol: dieldrin metabolite suggested as active neurotoxic form; RN refers to (1 alpha,2 alpha,3 beta,4 alpha,4a beta,5 alpha,8 alpha,8a beta)-isomer	3.06	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.	2.41	1	0
cyclosporine Cyclosporine: A cyclic undecapeptide from an extract of soil fungi. It is a powerful immunosupressant with a specific action on T-lymphocytes. It is used for the prophylaxis of graft rejection in organ and tissue transplantation. (From Martindale, The Extra Pharmacopoeia, 30th ed).	4	13	0
silybin Silybin: The major active component of silymarin flavonoids extracted from seeds of the MILK THISTLE, Silybum marianum; it is used in the treatment of HEPATITIS; LIVER CIRRHOSIS; and CHEMICAL AND DRUG INDUCED LIVER INJURY, and has antineoplastic activity; silybins A and B are diastereomers.	2.44	2	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.	2.42	2	0
asbestos, amosite Asbestos, Amosite: Asbestos, grunerite. A monoclinic amphibole form of asbestos having long fibers and a high iron content. It is used in insulation. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	2.67	3	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.	2.78	3	0
exudates Malaysia: A parliamentary democracy with a constitutional monarch in southeast Asia, consisting of 11 states (West Malaysia) on the Malay Peninsula and two states (East Malaysia) on the island of BORNEO. It is also called the Federation of Malaysia. Its capital is Kuala Lumpur. Before 1963 it was the Union of Malaya. It reorganized in 1948 as the Federation of Malaya, becoming independent from British Malaya in 1957 and becoming Malaysia in 1963 as a federation of Malaya, Sabah, Sarawak, and Singapore (which seceded in 1965). The form Malay- probably derives from the Tamil malay, mountain, with reference to its geography. (From Webster's New Geographical Dictionary, 1988, p715 & Room, Brewer's Dictionary of Names, 1992, p329)	2.15	1	0
plicamycin mithramycin A: structure given in first source	2.05	1	0
deoxyguanosine [no description available]	8.29	88	1	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
guanine [no description available]	6.83	34	0	2-aminopurines; oxopurine; purine nucleobase	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
guanosine ribonucleoside : Any nucleoside where the sugar component is D-ribose.	3.26	6	0	guanosines; purines D-ribonucleoside	fundamental metabolite
hypoxanthine [no description available]	2	1	0	nucleobase analogue; oxopurine; purine nucleobase	fundamental metabolite
folic acid folcysteine: used to promote fertility in chickens. vitamin B9 : Any B-vitamin that exhibits biological activity against vitamin B9 deficiency. Vitamin B9 refers to the many forms of folic acid and its derivatives, including tetrahydrofolic acid (the active form), methyltetrahydrofolate (the primary form found in blood), methenyltetrahydrofolate, folinic acid amongst others. They are present in abundance in green leafy vegetables, citrus fruits, and animal products. Lack of vitamin B9 leads to anemia, a condition in which the body cannot produce sufficient number of red blood cells. Symptoms of vitamin B9 deficiency include fatigue, muscle weakness, and pale skin.	3.05	4	0	folic acids; N-acyl-amino acid	human metabolite; mouse metabolite; nutrient
pheophytin a pheophytin a: structure given in first source; RN given refers to (3S-(3alpha(2E,7S,11S),4beta,21beta))-isomer	4.26	5	0
rifampin Rifampin: A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)	2.37	2	0	cyclic ketal; hydrazone; N-iminopiperazine; N-methylpiperazine; rifamycins; semisynthetic derivative; zwitterion	angiogenesis inhibitor; antiamoebic agent; antineoplastic agent; antitubercular agent; DNA synthesis inhibitor; EC 2.7.7.6 (RNA polymerase) inhibitor; Escherichia coli metabolite; geroprotector; leprostatic drug; neuroprotective agent; pregnane X receptor agonist; protein synthesis inhibitor
allopurinol Allopurinol: A XANTHINE OXIDASE inhibitor that decreases URIC ACID production. It also acts as an antimetabolite on some simpler organisms.. allopurinol : A bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring.	2.92	4	0	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger
azaguanine Azaguanine: One of the early purine analogs showing antineoplastic activity. It functions as an antimetabolite and is easily incorporated into ribonucleic acids.. 8-azaguanine : A triazolopyrimidine that consists of 3,6-dihydro-7H-[1,2,3]triazolo[4,5-d]pyrimidine bearing amino and oxo substituents at positions 5 and 7 respectively.	1.96	1	0	nucleobase analogue; triazolopyrimidines	antimetabolite; antineoplastic agent; EC 2.4.2.1 (purine-nucleoside phosphorylase) inhibitor
8-hydroxyguanosine 8-hydroxyguanosine: immunostimulant for B lymphocytes; structure given in first source	2.41	2	0	purine nucleoside
8-hydroxyguanine 7,8-dihydro-8-oxoguanine: was substituted for guanine at G(8), G(9), G(14), or G(15) in the human telomeric oligonucleotide 5'-d[AGGGTTAG(8)G(9)GTT AG(14)G(15)GTTAGGGTGT]-3'. 7,8-dihydro-8-oxoguanine : An oxopurine that is guanine in which the hydrogen at position 8 is replaced by an oxo group and in which the nitrogens at positions 7 and 9 each bear a hydrogen.	4.58	4	0	oxopurine
trypan blue Trypan Blue: A diazo-naphthalene sulfonate that is widely used as a stain.. trypan blue : An organosulfonate salt that is the tetrasodium salt of 3,3'-[(3,3'-dimethylbiphenyl-4,4'-diyl)didiazene-2,1-diyl]bis(5-amino-4-hydroxynaphthalene-2,7-disulfonic acid).	2.9	4	0
methylnitronitrosoguanidine Methylnitronitrosoguanidine: A nitrosoguanidine derivative with potent mutagenic and carcinogenic properties.. N-methyl-N'-nitro-N-nitrosoguanidine : An N-nitroguanidine compound having nitroso and methyl substituents at the N'-position	7.59	72	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.	6.31	35	1	guanosines	biomarker
enng [no description available]	4.52	9	0
imidacloprid imidacloprid: systemic & contact insecticide exhibiting low mammalian toxicity; structure given in first source; it is one of the neonicotinoid insecticides, which acts as an antagonist by binding to postsynaptic nicotinic receptors in the insect central nervous system. imidacloprid : An imidazolidine that is N-nitroimidazolidin-2-imine bearing a (6-chloro-3-pyridinyl)methyl substituent at position 1.	2.05	1	0	imidacloprid; imidazolidines; monochloropyridine	environmental contaminant; genotoxin; neonicotinoid insectide; nicotinic acetylcholine receptor agonist; xenobiotic
n-(deoxyguanosin-8-yl)-2-aminofluorene N-(deoxyguanosin-8-yl)-2-aminofluorene : Guanosine substituted at the purine 8-position by a (9H-fluoren-2-yl)amino group.	1.98	1	0	guanosines
aflatoxin b1-formamidopyrimidine aflatoxin B1-formamidopyrimidine: persistent aflatoxin-deoxyribonucleic acid(DNA) adduct	1.97	1	0
eye [no description available]	3.29	6	0
acetylcellulose acetylcellulose: coating compound. cellulose acetate : A glucan derivative obtained through the esterification of cellulose by acetic anhydride or acetic acid, resulting in the substitution of some of the hydroxy groups of cellulose by acetyl groups. It is used in a variety of applications including base material for photographic film, clothing, membrane filters, coatings, food packaging, and as a frame material for eyeglasses.	2.11	1	0
concanavalin a Concanavalin A: A MANNOSE/GLUCOSE binding lectin isolated from the jack bean (Canavalia ensiformis). It is a potent mitogen used to stimulate cell proliferation in lymphocytes, primarily T-lymphocyte, cultures.	2.91	4	0
metallothionein Metallothionein: A low-molecular-weight (approx. 10 kD) protein occurring in the cytoplasm of kidney cortex and liver. It is rich in cysteinyl residues and contains no aromatic amino acids. Metallothionein shows high affinity for bivalent heavy metals.	4.39	20	0
vermiculite [no description available]	2.03	1	0
dinitrobenzenes Dinitrobenzenes: Benzene derivatives which are substituted with two nitro groups in the ortho, meta or para positions.	1.97	1	0
hexachlorodibenzo-4-dioxin [no description available]	1.96	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.	7.87	79	0
forssman glycolipid Forssman glycolipid: structure	1.96	1	0
leptin Leptin: A 16-kDa peptide hormone secreted from WHITE ADIPOCYTES. Leptin serves as a feedback signal from fat cells to the CENTRAL NERVOUS SYSTEM in regulation of food intake, energy balance, and fat storage.	2.17	1	0
phenanthrenes Phenanthrenes: POLYCYCLIC AROMATIC HYDROCARBONS composed of three fused BENZENE rings.. phenanthrenes : Any benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof.	10.52	154	0

Condition	Relationship Strength	Studies	Trials
Innate Inflammatory Response [description not available]	12.88	66	16
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.	12.88	66	16
Depression Depressive states usually of moderate intensity in contrast with MAJOR DEPRESSIVE DISORDER present in neurotic and psychotic disorders.	2.81	3	0
Parasitemia The presence of parasites (especially malarial parasites) in the blood. (Dorland, 27th ed)	2.11	1	0
Infections, Plasmodium [description not available]	2.11	1	0
Malaria A protozoan disease caused in humans by four species of the PLASMODIUM genus: PLASMODIUM FALCIPARUM; PLASMODIUM VIVAX; PLASMODIUM OVALE; and PLASMODIUM MALARIAE; and transmitted by the bite of an infected female mosquito of the genus ANOPHELES. Malaria is endemic in parts of Asia, Africa, Central and South America, Oceania, and certain Caribbean islands. It is characterized by extreme exhaustion associated with paroxysms of high FEVER; SWEATING; shaking CHILLS; and ANEMIA. Malaria in ANIMALS is caused by other species of plasmodia.	2.11	1	0
Benign Neoplasms [description not available]	13.05	153	1
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	13.05	153	1
Anemia, Fanconi [description not available]	2.13	1	0
Fanconi Anemia Congenital disorder affecting all bone marrow elements, resulting in ANEMIA; LEUKOPENIA; and THROMBOPENIA, and associated with cardiac, renal, and limb malformations as well as dermal pigmentary changes. Spontaneous CHROMOSOME BREAKAGE is a feature of this disease along with predisposition to LEUKEMIA. There are at least 7 complementation groups in Fanconi anemia: FANCA, FANCB, FANCC, FANCD1, FANCD2, FANCE, FANCF, FANCG, and FANCL. (from Online Mendelian Inheritance in Man, http://www.ncbi.nlm.nih.gov/entrez/dispomim.cgi?id=227650, August 20, 2004)	2.13	1	0
Cardiac Toxicity [description not available]	2.81	3	0
Cardiotoxicity Damage to the HEART or its function secondary to exposure to toxic substances such as drugs used in CHEMOTHERAPY; IMMUNOTHERAPY; or RADIATION.	2.81	3	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.	10.62	279	0
Disbacteriosis [description not available]	3.48	6	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.	8.45	82	0
Cancer of Lung [description not available]	13.62	461	0
Lung Neoplasms Tumors or cancer of the LUNG.	13.62	461	0
Abnormality, Heart [description not available]	3.09	4	0
Heart Defects, Congenital Developmental abnormalities involving structures of the heart. These defects are present at birth but may be discovered later in life.	3.09	4	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	10.55	120	1
Colorectal Cancer [description not available]	7.46	19	1
Colorectal Neoplasms Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.	7.46	19	1
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	10.39	218	1
Diseases, Metabolic [description not available]	3.14	4	0
Metabolic Diseases Generic term for diseases caused by an abnormal metabolic process. It can be congenital due to inherited enzyme abnormality (METABOLISM, INBORN ERRORS) or acquired due to disease of an endocrine organ or failure of a metabolically important organ such as the liver. (Stedman, 26th ed)	3.14	4	0
Carcinoma, Non-Small Cell Lung [description not available]	4.31	18	0
Lymph Node Metastasis [description not available]	2.48	2	0
Carcinoma, Non-Small-Cell Lung A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.	4.31	18	0
Allergic Rhinitis [description not available]	5.12	2	1
Asthma, Bronchial [description not available]	8.97	17	4
Asthma A form of bronchial disorder with three distinct components: airway hyper-responsiveness (RESPIRATORY HYPERSENSITIVITY), airway INFLAMMATION, and intermittent AIRWAY OBSTRUCTION. It is characterized by spasmodic contraction of airway smooth muscle, WHEEZING, and dyspnea (DYSPNEA, PAROXYSMAL).	8.97	17	4
Rhinitis, Allergic An inflammation of the NASAL MUCOSA triggered by ALLERGENS.	5.12	2	1
Chronic Lung Injury [description not available]	5.28	10	1
Experimental Lung Inflammation Inflammation of any part, segment or lobe, of the lung parenchyma.	4.06	13	0
Pneumonia Infection of the lung often accompanied by inflammation.	4.06	13	0
Acute Liver Injury, Drug-Induced [description not available]	4.4	20	0
Acute Kidney Failure [description not available]	5.12	2	1
Chemical and Drug Induced Liver Injury A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.	4.4	20	0
Acute Kidney Injury Abrupt reduction in kidney function. Acute kidney injury encompasses the entire spectrum of the syndrome including acute kidney failure; ACUTE KIDNEY TUBULAR NECROSIS; and other less severe conditions.	5.12	2	1
Malignant Melanoma [description not available]	2.41	1	0
Melanoma A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)	2.41	1	0
Airway Remodeling The structural changes in the number, mass, size and/or composition of the airway tissues.	2.54	2	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	9.33	101	0
Delayed Effects, Prenatal Exposure [description not available]	6.06	43	0
Cognitive Decline [description not available]	8.07	3	0
Cognitive Dysfunction Diminished or impaired mental and/or intellectual function.	3.07	3	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.	2.88	3	0
Abortion, Tubal [description not available]	3.22	3	0
Abortion, Spontaneous Expulsion of the product of FERTILIZATION before completing the term of GESTATION and without deliberate interference.	3.22	3	0
Insulin Sensitivity [description not available]	2.82	2	0
Insulin Resistance Diminished effectiveness of INSULIN in lowering blood sugar levels: requiring the use of 200 units or more of insulin per day to prevent HYPERGLYCEMIA or KETOSIS.	2.82	2	0
Blood Poisoning [description not available]	2.41	1	0
Endotoxin Shock [description not available]	2.41	1	0
Salmonella Infections, Animal Infections in animals with bacteria of the genus SALMONELLA.	2.41	1	0
Shock, Septic Sepsis associated with HYPOTENSION or hypoperfusion despite adequate fluid resuscitation. Perfusion abnormalities may include but are not limited to LACTIC ACIDOSIS; OLIGURIA; or acute alteration in mental status.	2.41	1	0
Sepsis Systemic inflammatory response syndrome with a proven or suspected infectious etiology. When sepsis is associated with organ dysfunction distant from the site of infection, it is called severe sepsis. When sepsis is accompanied by HYPOTENSION despite adequate fluid infusion, it is called SEPTIC SHOCK.	2.41	1	0
Diathesis [description not available]	7.97	27	1
Cardiovascular Diseases Pathological conditions involving the CARDIOVASCULAR SYSTEM including the HEART; the BLOOD VESSELS; or the PERICARDIUM.	5.46	5	1
Fatty Liver, Nonalcoholic [description not available]	4.4	6	0
Non-alcoholic Fatty Liver Disease Fatty liver finding without excessive ALCOHOL CONSUMPTION.	4.4	6	0
Abortion, Missed The retention in the UTERUS of a dead FETUS two months or more after its DEATH.	2.6	1	0
Preterm Birth [description not available]	2.83	3	0
Premature Birth CHILDBIRTH before 37 weeks of PREGNANCY (259 days from the first day of the mother's last menstrual period, or 245 days after FERTILIZATION).	2.83	3	0
Sarcopenia Progressive decline in muscle mass due to aging which results in decreased functional capacity of muscles.	5.12	2	1
Depression, Involutional Form of depression in those MIDDLE AGE with feelings of ANXIETY.	2.41	1	0
Depressive Disorder, Major Disorder in which five (or more) of the following symptoms have been present during the same 2-week period and represent a change from previous functioning; at least one of the symptoms is either (1) depressed mood or (2) loss of interest or pleasure. Symptoms include: depressed mood most of the day, nearly every daily; markedly diminished interest or pleasure in activities most of the day, nearly every day; significant weight loss when not dieting or weight gain; Insomnia or hypersomnia nearly every day; psychomotor agitation or retardation nearly every day; fatigue or loss of energy nearly every day; feelings of worthlessness or excessive or inappropriate guilt; diminished ability to think or concentrate, or indecisiveness, nearly every day; or recurrent thoughts of death, recurrent suicidal ideation without a specific plan, or a suicide attempt. (DSM-5)	2.41	1	0
2019 Novel Coronavirus Disease [description not available]	8.55	7	4
Cancer of Mouth [description not available]	5.5	25	0
Mouth Neoplasms Tumors or cancer of the MOUTH.	5.5	25	0
Carcinoma, Squamous Cell of Head and Neck [description not available]	2.51	2	0
Squamous Cell Carcinoma of Head and Neck The most common type of head and neck carcinoma that originates from cells on the surface of the NASAL CAVITY; MOUTH; PARANASAL SINUSES, SALIVARY GLANDS, and LARYNX. Mutations in TNFRSF10B, PTEN, and ING1 genes are associated with this cancer.	2.51	2	0
Smoking Cessation Discontinuing the habit of SMOKING.	2.45	2	0
Cancer of Gastrointestinal Tract [description not available]	2.44	2	0
Impaired Glucose Tolerance [description not available]	2.66	2	0
Cardiometabolic Syndrome A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components not only include metabolic dysfunctions of METABOLIC SYNDROME but also HYPERTENSION, and ABDOMINAL OBESITY.	3.32	5	0
Prediabetes [description not available]	2.41	1	0
Prediabetic State The time period before the development of symptomatic diabetes. For example, certain risk factors can be observed in subjects who subsequently develop INSULIN RESISTANCE as in type 2 diabetes (DIABETES MELLITUS, TYPE 2).	2.41	1	0
Glucose Intolerance A pathological state in which BLOOD GLUCOSE level is less than approximately 140 mg/100 ml of PLASMA at fasting, and above approximately 200 mg/100 ml plasma at 30-, 60-, or 90-minute during a GLUCOSE TOLERANCE TEST. This condition is seen frequently in DIABETES MELLITUS, but also occurs with other diseases and MALNUTRITION.	2.66	2	0
Metabolic Syndrome A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components of metabolic syndrome include ABDOMINAL OBESITY; atherogenic DYSLIPIDEMIA; HYPERTENSION; HYPERGLYCEMIA; INSULIN RESISTANCE; a proinflammatory state; and a prothrombotic (THROMBOSIS) state.	3.32	5	0
Carcinoma, Anaplastic [description not available]	4.79	32	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.	9.79	32	0
Airflow Obstruction, Chronic [description not available]	2.6	1	0
Lung Adenocarcinoma [description not available]	4.2	15	0
Adenocarcinoma of Lung A carcinoma originating in the lung and the most common lung cancer type in never-smokers. Malignant cells exhibit distinct features such as glandular epithelial, or tubular morphology. Mutations in KRAS, EGFR, BRAF, and ERBB2 genes are associated with this cancer.	4.2	15	0
Pulmonary Disease, Chronic Obstructive A disease of chronic diffuse irreversible airflow obstruction. Subcategories of COPD include CHRONIC BRONCHITIS and PULMONARY EMPHYSEMA.	2.6	1	0
HIV Coinfection [description not available]	10.13	10	9
HIV Infections Includes the spectrum of human immunodeficiency virus infections that range from asymptomatic seropositivity, thru AIDS-related complex (ARC), to acquired immunodeficiency syndrome (AIDS).	10.13	10	9
Disease, Pulmonary [description not available]	5.25	12	0
Lung Diseases Pathological processes involving any part of the LUNG.	5.25	12	0
Cancer of Skin [description not available]	11.24	210	1
Skin Neoplasms Tumors or cancer of the SKIN.	11.24	210	1
Encephalopathy, Toxic [description not available]	4.42	18	0
Neuroblastoma A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)	6.06	8	1
Breast Cancer [description not available]	15.12	94	1
Breast Neoplasms Tumors or cancer of the human BREAST.	10.12	94	1
Age-Related Osteoporosis [description not available]	3.52	4	0
Osteoporosis Reduction of bone mass without alteration in the composition of bone, leading to fractures. Primary osteoporosis can be of two major types: postmenopausal osteoporosis (OSTEOPOROSIS, POSTMENOPAUSAL) and age-related or senile osteoporosis.	3.52	4	0
Cancer of Cervix [description not available]	4.62	10	0
Uterine Cervical Neoplasms Tumors or cancer of the UTERINE CERVIX.	4.62	10	0
Polyploid [description not available]	2.72	3	0
Injury, Myocardial Reperfusion [description not available]	2.6	1	0
Lung Injury, Acute [description not available]	3.72	8	0
Grippe [description not available]	2.6	1	0
Influenza, Human An acute viral infection in humans involving the respiratory tract. It is marked by inflammation of the NASAL MUCOSA; the PHARYNX; and conjunctiva, and by headache and severe, often generalized, myalgia.	2.6	1	0
Acute Lung Injury A condition of lung damage that is characterized by bilateral pulmonary infiltrates (PULMONARY EDEMA) rich in NEUTROPHILS, and in the absence of clinical HEART FAILURE. This can represent a spectrum of pulmonary lesions, endothelial and epithelial, due to numerous factors (physical, chemical, or biological).	8.72	8	0
Hepatocellular Carcinoma [description not available]	12.48	75	0
Cancer of Liver [description not available]	7.65	89	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.	7.48	75	0
Liver Neoplasms Tumors or cancer of the LIVER.	7.65	89	0
Kidney Failure A severe irreversible decline in the ability of kidneys to remove wastes, concentrate URINE, and maintain ELECTROLYTE BALANCE; BLOOD PRESSURE; and CALCIUM metabolism.	2.6	1	0
Renal Insufficiency Conditions in which the KIDNEYS perform below the normal level in the ability to remove wastes, concentrate URINE, and maintain ELECTROLYTE BALANCE; BLOOD PRESSURE; and CALCIUM metabolism. Renal insufficiency can be classified by the degree of kidney damage (as measured by the level of PROTEINURIA) and reduction in GLOMERULAR FILTRATION RATE.	2.6	1	0
Atherogenesis [description not available]	3.58	8	0
Atherosclerosis A thickening and loss of elasticity of the walls of ARTERIES that occurs with formation of ATHEROSCLEROTIC PLAQUES within the ARTERIAL INTIMA.	8.58	8	0
Cancer of Prostate [description not available]	7.2	15	1
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	7.2	15	1
Autoimmune Disease [description not available]	2.6	1	0
Libman-Sacks Disease [description not available]	5.08	3	1
Autoimmune Diseases Disorders that are characterized by the production of antibodies that react with host tissues or immune effector cells that are autoreactive to endogenous peptides.	2.6	1	0
Lupus Erythematosus, Systemic A chronic, relapsing, inflammatory, and often febrile multisystemic disorder of connective tissue, characterized principally by involvement of the skin, joints, kidneys, and serosal membranes. It is of unknown etiology, but is thought to represent a failure of the regulatory mechanisms of the autoimmune system. The disease is marked by a wide range of system dysfunctions, an elevated erythrocyte sedimentation rate, and the formation of LE cells in the blood or bone marrow.	5.08	3	1
Cardiovascular Stroke [description not available]	2.52	2	0
Myocardial Infarction NECROSIS of the MYOCARDIUM caused by an obstruction of the blood supply to the heart (CORONARY CIRCULATION).	2.52	2	0
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	5.61	29	0
Dyslipidemia [description not available]	3.14	1	0
Atheroma [description not available]	3.14	1	0
Dyslipidemias Abnormalities in the serum levels of LIPIDS, including overproduction or deficiency. Abnormal serum lipid profiles may include high total CHOLESTEROL, high TRIGLYCERIDES, low HIGH DENSITY LIPOPROTEIN CHOLESTEROL, and elevated LOW DENSITY LIPOPROTEIN CHOLESTEROL.	3.14	1	0
Carcinoma, Small Cell Lung [description not available]	2.76	2	0
Small Cell Lung Carcinoma A form of highly malignant lung cancer that is composed of small ovoid cells (SMALL CELL CARCINOMA).	2.76	2	0
Diseases of Endocrine System [description not available]	3.14	1	0
Endocrine System Diseases Pathological processes of the ENDOCRINE GLANDS, and diseases resulting from abnormal level of available HORMONES.	3.14	1	0
Respiration Disorders Diseases of the respiratory system in general or unspecified or for a specific respiratory disease not available.	2.6	1	0
Respiratory Tract Diseases Diseases involving the RESPIRATORY SYSTEM.	6.28	8	1
Experimental Neoplasms [description not available]	11.13	165	1
Chromosome-Defective Micronuclei [description not available]	5.18	46	0
Degenerative Diseases, Central Nervous System [description not available]	3.08	4	0
Neurodegenerative Diseases Hereditary and sporadic conditions which are characterized by progressive nervous system dysfunction. These disorders are often associated with atrophy of the affected central or peripheral nervous system structures.	3.08	4	0
Colonic Diseases Pathological processes in the COLON region of the large intestine (INTESTINE, LARGE).	2.21	1	0
Invasiveness, Neoplasm [description not available]	7.18	20	1
Cancer of Colon [description not available]	7.61	38	0
Colonic Neoplasms Tumors or cancer of the COLON.	7.61	38	0
Alloxan Diabetes [description not available]	3.24	6	0
Diabetes Mellitus, Adult-Onset [description not available]	5.54	5	1
Adenoma, beta-Cell [description not available]	2.21	1	0
Cancer of Pancreas [description not available]	5.2	11	0
Diabetes Mellitus, Type 2 A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.	5.54	5	1
Insulinoma A benign tumor of the PANCREATIC BETA CELLS. Insulinoma secretes excess INSULIN resulting in HYPOGLYCEMIA.	2.21	1	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).	5.2	11	0
Dermatitis, Contact, Phototoxic [description not available]	2.68	3	0
Disease Exacerbation [description not available]	5.22	18	0
Angiogenesis, Pathologic [description not available]	4.66	10	0
Carcinoma, Epidermoid [description not available]	5.76	86	0
Cancer of the Tongue [description not available]	2.38	2	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)	5.76	86	0
Tongue Neoplasms Tumors or cancer of the TONGUE.	2.38	2	0
Fish Diseases Diseases of freshwater, marine, hatchery or aquarium fish. This term includes diseases of both teleosts (true fish) and elasmobranchs (sharks, rays and skates).	5.72	7	1
Electron Transport Chain Deficiencies, Mitochondrial [description not available]	2.52	2	0
Mitochondrial Diseases Diseases caused by abnormal function of the MITOCHONDRIA. They may be caused by mutations, acquired or inherited, in mitochondrial DNA or in nuclear genes that code for mitochondrial components. They may also be the result of acquired mitochondria dysfunction due to adverse effects of drugs, infections, or other environmental causes.	2.52	2	0
Acute Brain Injuries [description not available]	2.25	1	0
Brain Injuries Acute and chronic (see also BRAIN INJURIES, CHRONIC) injuries to the brain, including the cerebral hemispheres, CEREBELLUM, and BRAIN STEM. Clinical manifestations depend on the nature of injury. Diffuse trauma to the brain is frequently associated with DIFFUSE AXONAL INJURY or COMA, POST-TRAUMATIC. Localized injuries may be associated with NEUROBEHAVIORAL MANIFESTATIONS; HEMIPARESIS, or other focal neurologic deficits.	2.25	1	0
Metastase [description not available]	5.2	11	0
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	5.2	11	0
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	6.33	59	0
Cryptogenic Fibrosing Alveolitis [description not available]	2.25	1	0
Cirrhosis [description not available]	2.58	2	0
Idiopathic Interstitial Pneumonia [description not available]	2.25	1	0
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	2.58	2	0
Idiopathic Pulmonary Fibrosis A common interstitial lung disease of unknown etiology, usually occurring between 50-70 years of age. Clinically, it is characterized by an insidious onset of breathlessness with exertion and a nonproductive cough, leading to progressive DYSPNEA. Pathological features show scant interstitial inflammation, patchy collagen fibrosis, prominent fibroblast proliferation foci, and microscopic honeycomb change.	2.25	1	0
Genetic Predisposition [description not available]	7.1	19	1
Chronic Illness [description not available]	5.41	5	1
Cardiac Death [description not available]	4.72	1	1
Infections, Coronavirus [description not available]	7.84	4	4
Chronic Hepatitis C [description not available]	7.84	4	4
Cerebral Infarction, Middle Cerebral Artery [description not available]	4.72	1	1
Cardiac Remodeling, Ventricular [description not available]	4.72	1	1
Acute Relapsing Multiple Sclerosis [description not available]	4.72	1	1
Peripheral Arterial Diseases [description not available]	4.72	1	1
Co-infection [description not available]	4.72	1	1
Epithelial Ovarian Cancer [description not available]	4.72	1	1
ALS - Amyotrophic Lateral Sclerosis [description not available]	4.72	1	1
Adjuvant Arthritis [description not available]	4.72	1	1
Rheumatoid Arthritis [description not available]	5.12	3	1
Bacterial Disease [description not available]	4.72	2	1
Benign Neoplasms, Brain [description not available]	4.87	2	1
Cardiomyopathy, Hypertrophic Obstructive [description not available]	4.72	1	1
Cerebral Ischemia [description not available]	7.84	4	4
Catarrh Inflammation of a mucous membrane with increased flow of mucous in humans or animals. Catarrh is used mostly in a historical context.	4.72	1	1
Endometrioma An enlarged area of ENDOMETRIOSIS that resembles a tumor. It is usually found in the OVARY. When it is filled with old blood, it is known as a chocolate cyst.	5.11	3	1
E coli Infections [description not available]	4.74	2	1
Cancer of Esophagus [description not available]	6.97	12	1
Berger Disease [description not available]	4.72	1	1
Hepatitis, Viral, Non-A, Non-B, Parenterally-Transmitted [description not available]	4.72	1	1
Blood Pressure, High [description not available]	5.27	4	1
Central Hypothyroidism [description not available]	4.72	1	1
Chronic Kidney Failure [description not available]	4.72	1	1
Cirrhosis, Liver [description not available]	5.07	2	1
Age-Related Macular Degeneration [description not available]	4.99	2	1
MS (Multiple Sclerosis) [description not available]	4.72	1	1
Arthritis, Degenerative [description not available]	5.07	2	1
Cancer of Ovary [description not available]	5.71	7	1
Complication, Postoperative [description not available]	7.84	4	4
Sarcoma, Epithelioid [description not available]	5.76	8	1
Shock, Cardiogenic Shock resulting from diminution of cardiac output in heart disease.	4.72	1	1
Sinus Infections [description not available]	4.72	1	1
Infections, Staphylococcal [description not available]	4.72	1	1
Cancer of Stomach [description not available]	12.21	99	5
Cancer of the Thyroid [description not available]	4.72	1	1
Injury, Ischemia-Reperfusion [description not available]	7.84	4	4
Plasmodium falciparum Malaria [description not available]	4.72	1	1
Bacterial Infections, Gram-Negative [description not available]	4.87	2	1
Bacterial Infections, Gram-Positive [description not available]	4.72	1	1
Low Back Ache [description not available]	4.72	1	1
Heart Disease, Ischemic [description not available]	4.72	1	1
Local Neoplasm Recurrence [description not available]	7.84	4	4
Bucket Handle Tears [description not available]	4.72	1	1
Carcinoma, Ovarian Epithelial A malignant neoplasm that originates in cells on the surface EPITHELIUM of the ovary and is the most common form of ovarian cancer. There are five histologic subtypes: papillary serous, endometrioid, mucinous, clear cell, and transitional cell. Mutations in BRCA1, OPCML, PRKN, PIK3CA, AKT1, CTNNB1, RRAS2, and CDH1 genes are associated with this cancer.	4.72	1	1
Amyotrophic Lateral Sclerosis A degenerative disorder affecting upper MOTOR NEURONS in the brain and lower motor neurons in the brain stem and SPINAL CORD. Disease onset is usually after the age of 50 and the process is usually fatal within 3 to 6 years. Clinical manifestations include progressive weakness, atrophy, FASCICULATION, hyperreflexia, DYSARTHRIA, dysphagia, and eventual paralysis of respiratory function. Pathologic features include the replacement of motor neurons with fibrous ASTROCYTES and atrophy of anterior SPINAL NERVE ROOTS and corticospinal tracts. (From Adams et al., Principles of Neurology, 6th ed, pp1089-94)	4.72	1	1
Arthritis, Rheumatoid A chronic systemic disease, primarily of the joints, marked by inflammatory changes in the synovial membranes and articular structures, widespread fibrinoid degeneration of the collagen fibers in mesenchymal tissues, and by atrophy and rarefaction of bony structures. Etiology is unknown, but autoimmune mechanisms have been implicated.	5.12	3	1
Bacterial Infections Infections by bacteria, general or unspecified.	4.72	2	1
Brain Neoplasms Neoplasms of the intracranial components of the central nervous system, including the cerebral hemispheres, basal ganglia, hypothalamus, thalamus, brain stem, and cerebellum. Brain neoplasms are subdivided into primary (originating from brain tissue) and secondary (i.e., metastatic) forms. Primary neoplasms are subdivided into benign and malignant forms. In general, brain tumors may also be classified by age of onset, histologic type, or presenting location in the brain.	4.87	2	1
Cardiomyopathy, Hypertrophic A form of CARDIAC MUSCLE disease, characterized by left and/or right ventricular hypertrophy (HYPERTROPHY, LEFT VENTRICULAR; HYPERTROPHY, RIGHT VENTRICULAR), frequent asymmetrical involvement of the HEART SEPTUM, and normal or reduced left ventricular volume. Risk factors include HYPERTENSION; AORTIC STENOSIS; and gene MUTATION; (FAMILIAL HYPERTROPHIC CARDIOMYOPATHY).	4.72	1	1
Brain Ischemia Localized reduction of blood flow to brain tissue due to arterial obstruction or systemic hypoperfusion. This frequently occurs in conjunction with brain hypoxia (HYPOXIA, BRAIN). Prolonged ischemia is associated with BRAIN INFARCTION.	7.84	4	4
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).	5.41	5	1
Common Cold A catarrhal disorder of the upper respiratory tract, which may be viral or a mixed infection. It generally involves a runny nose, nasal congestion, and sneezing.	4.72	1	1
Electrolytes Substances that dissociate into two or more ions, to some extent, in water. Solutions of electrolytes thus conduct an electric current and can be decomposed by it (ELECTROLYSIS). (Grant & Hackh's Chemical Dictionary, 5th ed)	4.72	1	1
Endometriosis A condition in which functional endometrial tissue is present outside the UTERUS. It is often confined to the PELVIS involving the OVARY, the ligaments, cul-de-sac, and the uterovesical peritoneum.	5.11	3	1
Escherichia coli Infections Infections with bacteria of the species ESCHERICHIA COLI.	4.74	2	1
Esophageal Neoplasms Tumors or cancer of the ESOPHAGUS.	6.97	12	1
Glomerulonephritis, IGA A chronic form of glomerulonephritis characterized by deposits of predominantly IMMUNOGLOBULIN A in the mesangial area (GLOMERULAR MESANGIUM). Deposits of COMPLEMENT C3 and IMMUNOGLOBULIN G are also often found. Clinical features may progress from asymptomatic HEMATURIA to END-STAGE KIDNEY DISEASE.	4.72	1	1
Hepatitis C INFLAMMATION of the LIVER in humans caused by HEPATITIS C VIRUS, a single-stranded RNA virus. Its incubation period is 30-90 days. Hepatitis C is transmitted primarily by contaminated blood parenterally and is often associated with transfusion and intravenous drug abuse. However, in a significant number of cases, the source of hepatitis C infection is unknown.	4.72	1	1
Hypertension Persistently high systemic arterial BLOOD PRESSURE. Based on multiple readings (BLOOD PRESSURE DETERMINATION), hypertension is currently defined as when SYSTOLIC PRESSURE is consistently greater than 140 mm Hg or when DIASTOLIC PRESSURE is consistently 90 mm Hg or more.	5.27	4	1
Hypothyroidism A syndrome that results from abnormally low secretion of THYROID HORMONES from the THYROID GLAND, leading to a decrease in BASAL METABOLIC RATE. In its most severe form, there is accumulation of MUCOPOLYSACCHARIDES in the SKIN and EDEMA, known as MYXEDEMA. It may be primary or secondary due to other pituitary disease, or hypothalamic dysfunction.	4.72	1	1
Intermittent Claudication A symptom complex characterized by pain and weakness in SKELETAL MUSCLE group associated with exercise, such as leg pain and weakness brought on by walking. Such muscle limpness disappears after a brief rest and is often relates to arterial STENOSIS; muscle ISCHEMIA; and accumulation of LACTATE.	4.72	1	1
Kidney Failure, Chronic The end-stage of CHRONIC RENAL INSUFFICIENCY. It is characterized by the severe irreversible kidney damage (as measured by the level of PROTEINURIA) and the reduction in GLOMERULAR FILTRATION RATE to less than 15 ml per min (Kidney Foundation: Kidney Disease Outcome Quality Initiative, 2002). These patients generally require HEMODIALYSIS or KIDNEY TRANSPLANTATION.	4.72	1	1
Liver Cirrhosis Liver disease in which the normal microcirculation, the gross vascular anatomy, and the hepatic architecture have been variably destroyed and altered with fibrous septa surrounding regenerated or regenerating parenchymal nodules.	5.07	2	1
Macular Degeneration Degenerative changes in the RETINA usually of older adults which results in a loss of vision in the center of the visual field (the MACULA LUTEA) because of damage to the retina. It occurs in dry and wet forms.	4.99	2	1
Multiple Sclerosis An autoimmune disorder mainly affecting young adults and characterized by destruction of myelin in the central nervous system. Pathologic findings include multiple sharply demarcated areas of demyelination throughout the white matter of the central nervous system. Clinical manifestations include visual loss, extra-ocular movement disorders, paresthesias, loss of sensation, weakness, dysarthria, spasticity, ataxia, and bladder dysfunction. The usual pattern is one of recurrent attacks followed by partial recovery (see MULTIPLE SCLEROSIS, RELAPSING-REMITTING), but acute fulminating and chronic progressive forms (see MULTIPLE SCLEROSIS, CHRONIC PROGRESSIVE) also occur. (Adams et al., Principles of Neurology, 6th ed, p903)	4.72	1	1
Osteoarthritis A progressive, degenerative joint disease, the most common form of arthritis, especially in older persons. The disease is thought to result not from the aging process but from biochemical changes and biomechanical stresses affecting articular cartilage. In the foreign literature it is often called osteoarthrosis deformans.	5.07	2	1
Ovarian Neoplasms Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.	5.71	7	1
Pneumonia, Viral Inflammation of the lung parenchyma that is caused by a viral infection.	7.84	4	4
Postoperative Complications Pathologic processes that affect patients after a surgical procedure. They may or may not be related to the disease for which the surgery was done, and they may or may not be direct results of the surgery.	7.84	4	4
Sarcoma A connective tissue neoplasm formed by proliferation of mesodermal cells; it is usually highly malignant.	10.76	8	1
Sinusitis Inflammation of the NASAL MUCOSA in one or more of the PARANASAL SINUSES.	4.72	1	1
Staphylococcal Infections Infections with bacteria of the genus STAPHYLOCOCCUS.	4.72	1	1
Stomach Neoplasms Tumors or cancer of the STOMACH.	12.21	99	5
Thyroid Neoplasms Tumors or cancer of the THYROID GLAND.	4.72	1	1
Reperfusion Injury Adverse functional, metabolic, or structural changes in tissues that result from the restoration of blood flow to the tissue (REPERFUSION) following ISCHEMIA.	7.84	4	4
Malaria, Falciparum Malaria caused by PLASMODIUM FALCIPARUM. This is the severest form of malaria and is associated with the highest levels of parasites in the blood. This disease is characterized by irregularly recurring febrile paroxysms that in extreme cases occur with acute cerebral, renal, or gastrointestinal manifestations.	4.72	1	1
Gram-Negative Bacterial Infections Infections caused by bacteria that show up as pink (negative) when treated by the gram-staining method.	4.87	2	1
Gram-Positive Bacterial Infections Infections caused by bacteria that retain the crystal violet stain (positive) when treated by the gram-staining method.	4.72	1	1
Low Back Pain Acute or chronic pain in the lumbar or sacral regions, which may be associated with musculo-ligamentous SPRAINS AND STRAINS; INTERVERTEBRAL DISK DISPLACEMENT; and other conditions.	4.72	1	1
Myocardial Ischemia A disorder of cardiac function caused by insufficient blood flow to the muscle tissue of the heart. The decreased blood flow may be due to narrowing of the coronary arteries (CORONARY ARTERY DISEASE), to obstruction by a thrombus (CORONARY THROMBOSIS), or less commonly, to diffuse narrowing of arterioles and other small vessels within the heart. Severe interruption of the blood supply to the myocardial tissue may result in necrosis of cardiac muscle (MYOCARDIAL INFARCTION).	4.72	1	1
Coronavirus Infections Virus diseases caused by the CORONAVIRUS genus. Some specifics include transmissible enteritis of turkeys (ENTERITIS, TRANSMISSIBLE, OF TURKEYS); FELINE INFECTIOUS PERITONITIS; and transmissible gastroenteritis of swine (GASTROENTERITIS, TRANSMISSIBLE, OF SWINE).	7.84	4	4
Hepatitis C, Chronic INFLAMMATION of the LIVER in humans that is caused by HEPATITIS C VIRUS lasting six months or more. Chronic hepatitis C can lead to LIVER CIRRHOSIS.	7.84	4	4
Infarction, Middle Cerebral Artery NECROSIS occurring in the MIDDLE CEREBRAL ARTERY distribution system which brings blood to the entire lateral aspects of each CEREBRAL HEMISPHERE. Clinical signs include impaired cognition; APHASIA; AGRAPHIA; weak and numbness in the face and arms, contralaterally or bilaterally depending on the infarction.	4.72	1	1
Multiple Sclerosis, Relapsing-Remitting The most common clinical variant of MULTIPLE SCLEROSIS, characterized by recurrent acute exacerbations of neurologic dysfunction followed by partial or complete recovery. Common clinical manifestations include loss of visual (see OPTIC NEURITIS), motor, sensory, or bladder function. Acute episodes of demyelination may occur at any site in the central nervous system, and commonly involve the optic nerves, spinal cord, brain stem, and cerebellum. (Adams et al., Principles of Neurology, 6th ed, pp903-914)	4.72	1	1
Peripheral Arterial Disease Lack of perfusion in the EXTREMITIES resulting from atherosclerosis. It is characterized by INTERMITTENT CLAUDICATION, and an ANKLE BRACHIAL INDEX of 0.9 or less.	4.72	1	1
Acute Pain Intensely discomforting, distressful, or agonizing sensation associated with trauma or disease, with well-defined location, character, and timing.	4.72	1	1
Amyloid Deposits [description not available]	2.25	1	0
Acute Confusional Senile Dementia [description not available]	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
Abortion, Recurrent [description not available]	2.69	2	0
Abortion, Habitual Three or more consecutive spontaneous abortions.	2.69	2	0
Anxiety Feelings or emotions of dread, apprehension, and impending disaster but not disabling as with ANXIETY DISORDERS.	3.61	8	0
Experimental Mammary Neoplasms [description not available]	5.02	16	0
Weight Gain Increase in BODY WEIGHT over existing weight.	3.74	10	0
Cocarcinogenesis The combination of two or more different factors in the production of cancer.	7.68	85	0
Skin Aging The process of aging due to changes in the structure and elasticity of the skin over time. It may be a part of physiological aging or it may be due to the effects of ultraviolet radiation, usually through exposure to sunlight.	2.69	2	0
Alveolitis, Fibrosing [description not available]	2.96	4	0
Pulmonary Fibrosis A process in which normal lung tissues are progressively replaced by FIBROBLASTS and COLLAGEN causing an irreversible loss of the ability to transfer oxygen into the bloodstream via PULMONARY ALVEOLI. Patients show progressive DYSPNEA finally resulting in death.	2.96	4	0
Bone Loss, Osteoclastic [description not available]	2.83	3	0
a-Synucleinopathies [description not available]	2.31	1	0
Atherosclerotic Parkinsonism [description not available]	2.31	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)	2.31	1	0
Liver Dysfunction [description not available]	3.08	5	0
Liver Diseases Pathological processes of the LIVER.	3.08	5	0
Cancer of the Uterus [description not available]	2.7	3	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).	3.12	5	0
Uterine Neoplasms Tumors or cancer of the UTERUS.	2.7	3	0
Cancer of Endometrium [description not available]	2.98	4	0
Endometrial Neoplasms Tumors or cancer of ENDOMETRIUM, the mucous lining of the UTERUS. These neoplasms can be benign or malignant. Their classification and grading are based on the various cell types and the percent of undifferentiated cells.	2.98	4	0
Adenocarcinoma, Basal Cell [description not available]	6.42	65	0
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	6.42	65	0
Abnormalities, Autosome [description not available]	6.74	92	0
Bladder Cancer [description not available]	5.51	11	0
Urinary Bladder Neoplasms Tumors or cancer of the URINARY BLADDER.	5.51	11	0
Sterility, Female [description not available]	2.78	3	0
Infertility, Female Diminished or absent ability of a female to achieve conception.	2.78	3	0
Environmental Hypersensitivities [description not available]	2.15	1	0
Germinoblastoma [description not available]	5.04	16	0
Lymphoma A general term for various neoplastic diseases of the lymphoid tissue.	5.04	16	0
Genome Instability [description not available]	4.5	8	0
Hyperoxia An abnormal increase in the amount of oxygen in the tissues and organs.	3.66	3	0
Acrania [description not available]	2.17	1	0
Neural Tube Defects Congenital malformations of the central nervous system and adjacent structures related to defective neural tube closure during the first trimester of pregnancy generally occurring between days 18-29 of gestation. Ectodermal and mesodermal malformations (mainly involving the skull and vertebrae) may occur as a result of defects of neural tube closure. (From Joynt, Clinical Neurology, 1992, Ch55, pp31-41)	2.17	1	0
Liver Steatosis [description not available]	2.83	3	0
Fatty Liver Lipid infiltration of the hepatic parenchymal cells resulting in a yellow-colored liver. The abnormal lipid accumulation is usually in the form of TRIGLYCERIDES, either as a single large droplet or multiple small droplets. Fatty liver is caused by an imbalance in the metabolism of FATTY ACIDS.	2.83	3	0
Colitis Gravis [description not available]	2.41	2	0
Colitis, Ulcerative Inflammation of the COLON that is predominantly confined to the MUCOSA. Its major symptoms include DIARRHEA, rectal BLEEDING, the passage of MUCUS, and ABDOMINAL PAIN.	2.41	2	0
Neoplasms, Bronchial [description not available]	3.67	10	0
Bronchial Neoplasms Tumors or cancer of the BRONCHI.	3.67	10	0
Acute Edematous Pancreatitis [description not available]	2.17	1	0
Pancreatitis INFLAMMATION of the PANCREAS. Pancreatitis is classified as acute unless there are computed tomographic or endoscopic retrograde cholangiopancreatographic findings of CHRONIC PANCREATITIS (International Symposium on Acute Pancreatitis, Atlanta, 1992). The two most common forms of acute pancreatitis are ALCOHOLIC PANCREATITIS and gallstone pancreatitis.	2.17	1	0
Adolescent Obesity [description not available]	2.17	1	0
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	9.04	14	0
Adenoma, Basal Cell [description not available]	7.92	46	0
Adenoma A benign epithelial tumor with a glandular organization.	7.92	46	0
Abdominal Aortic Aneurysm [description not available]	3.19	5	0
Aortic Aneurysm, Abdominal An abnormal balloon- or sac-like dilatation in the wall of the ABDOMINAL AORTA which gives rise to the visceral, the parietal, and the terminal (iliac) branches below the aortic hiatus at the diaphragm.	3.19	5	0
Neurogenic Inflammation Inflammation caused by an injurious stimulus of peripheral neurons and resulting in release of neuropeptides which affect vascular permeability and help initiate proinflammatory and immune reactions at the site of injury.	2.21	1	0
Allergic Contact Dermatitis [description not available]	2.45	2	0
Dermatitis, Allergic Contact A contact dermatitis due to allergic sensitization to various substances. These substances subsequently produce inflammatory reactions in the skin of those who have acquired hypersensitivity to them as a result of prior exposure.	2.45	2	0
ANS (Autonomic Nervous System) Diseases [description not available]	2.46	2	0
Nervous System Disorders [description not available]	2.91	4	0
Diseases, Occupational [description not available]	7.7	41	0
Nervous System Diseases Diseases of the central and peripheral nervous system. This includes disorders of the brain, spinal cord, cranial nerves, peripheral nerves, nerve roots, autonomic nervous system, neuromuscular junction, and muscle.	2.91	4	0
Varices [description not available]	2.08	1	0
Varicose Veins Enlarged and tortuous VEINS.	2.08	1	0
Cancer of Rectum [description not available]	3.34	2	0
Rectal Neoplasms Tumors or cancer of the RECTUM.	3.34	2	0
Anoxemia [description not available]	3.44	7	0
Hypoxia Sub-optimal OXYGEN levels in the ambient air of living organisms.	3.44	7	0
Cirrhoses, Experimental Liver [description not available]	2.08	1	0
Ascites Accumulation or retention of free fluid within the peritoneal cavity.	2.65	3	0
Cancer of Intestines [description not available]	4.18	6	0
Intestinal Neoplasms Tumors or cancer of the INTESTINES.	4.18	6	0
Porphyria [description not available]	2.68	3	0
Porphyrias A diverse group of metabolic diseases characterized by errors in the biosynthetic pathway of HEME in the LIVER, the BONE MARROW, or both. They are classified by the deficiency of specific enzymes, the tissue site of enzyme defect, or the clinical features that include neurological (acute) or cutaneous (skin lesions). Porphyrias can be hereditary or acquired as a result of toxicity to the hepatic or erythropoietic marrow tissues.	2.68	3	0
Condition, Preneoplastic [description not available]	7.41	32	0
Precancerous Conditions Pathological conditions that tend eventually to become malignant.	7.41	32	0
Birth Weight The mass or quantity of heaviness of an individual at BIRTH. It is expressed by units of pounds or kilograms.	8.27	6	0
Degenerative Disease, Nervous System, Hereditary [description not available]	2.08	1	0
Microphthalmia [description not available]	2.4	2	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).	2.92	4	0
Cancer, Radiation-Induced [description not available]	4.5	9	0
Craniofacial Abnormalities Congenital structural deformities, malformations, or other abnormalities of the cranium and facial bones.	2.48	2	0
Extravascular Hemolysis [description not available]	3.61	9	0
Hemolysis The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.	3.61	9	0
Dermatitis Any inflammation of the skin.	2.1	1	0
Carcinoma, Ehrlich Tumor A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.	2.65	3	0
EHS Tumor [description not available]	4.64	28	0
Abortion, Veterinary Premature expulsion of the FETUS in animals.	2.1	1	0
Kahler Disease [description not available]	2.11	1	0
Multiple Myeloma A malignancy of mature PLASMA CELLS engaging in monoclonal immunoglobulin production. It is characterized by hyperglobulinemia, excess Bence-Jones proteins (free monoclonal IMMUNOGLOBULIN LIGHT CHAINS) in the urine, skeletal destruction, bone pain, and fractures. Other features include ANEMIA; HYPERCALCEMIA; and RENAL INSUFFICIENCY.	2.11	1	0
Experimental Hepatoma [description not available]	6.31	60	0
Cardiac Hypertrophy Enlargement of the HEART due to chamber HYPERTROPHY, an increase in wall thickness without an increase in the number of cells (MYOCYTES, CARDIAC). It is the result of increase in myocyte size, mitochondrial and myofibrillar mass, as well as changes in extracellular matrix.	2.76	3	0
Cardiomegaly Enlargement of the HEART, usually indicated by a cardiothoracic ratio above 0.50. Heart enlargement may involve the right, the left, or both HEART VENTRICLES or HEART ATRIA. Cardiomegaly is a nonspecific symptom seen in patients with chronic systolic heart failure (HEART FAILURE) or several forms of CARDIOMYOPATHIES.	2.76	3	0
Palmoplantaris Pustulosis [description not available]	3.49	8	0
Psoriasis A common genetically determined, chronic, inflammatory skin disease characterized by rounded erythematous, dry, scaling patches. The lesions have a predilection for nails, scalp, genitalia, extensor surfaces, and the lumbosacral region. Accelerated epidermopoiesis is considered to be the fundamental pathologic feature in psoriasis.	8.49	8	0
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	2.73	3	0
Animal Mammary Carcinoma [description not available]	3.8	4	0
Bone Cancer [description not available]	2.4	2	0
Bone Neoplasms Tumors or cancer located in bone tissue or specific BONES.	2.4	2	0
Microsatellite Instability The occurrence of highly polymorphic mono- and dinucleotide MICROSATELLITE REPEATS in somatic cells. It is a form of genome instability associated with defects in DNA MISMATCH REPAIR.	2.11	1	0
Cancer of Kidney [description not available]	3.03	1	0
Kidney Neoplasms Tumors or cancers of the KIDNEY.	3.03	1	0
Papilloma, Squamous Cell [description not available]	7.65	57	1
Papilloma A circumscribed benign epithelial tumor projecting from the surrounding surface; more precisely, a benign epithelial neoplasm consisting of villous or arborescent outgrowths of fibrovascular stroma covered by neoplastic cells. (Stedman, 25th ed)	7.65	57	1
Keratosis, Oral [description not available]	3.66	3	0
Leukoplakia, Oral A white patch seen on the oral mucosa. It is considered a premalignant condition and is often tobacco-induced. When evidence of Epstein-Barr virus is present, the condition is called hairy leukoplakia (LEUKOPLAKIA, HAIRY).	3.66	3	0
Symptom Cluster [description not available]	2.11	1	0
Syndrome A characteristic symptom complex.	2.11	1	0
Academic Disorder, Developmental [description not available]	2.76	3	0
Learning Disabilities Conditions characterized by a significant discrepancy between an individual's perceived level of intellect and their ability to acquire new language and other cognitive skills. These may result from organic or psychological conditions. Relatively common subtypes include DYSLEXIA, DYSCALCULIA, and DYSGRAPHIA.	2.76	3	0
Cancer of Head [description not available]	2.95	4	0
Kaposi Disease [description not available]	3.85	12	0
Head and Neck Neoplasms Soft tissue tumors or cancer arising from the mucosal surfaces of the LIP; oral cavity; PHARYNX; LARYNX; and cervical esophagus. Other sites included are the NOSE and PARANASAL SINUSES; SALIVARY GLANDS; THYROID GLAND and PARATHYROID GLANDS; and MELANOMA and non-melanoma skin cancers of the head and neck. (from Holland et al., Cancer Medicine, 4th ed, p1651)	2.95	4	0
Xeroderma Pigmentosum A rare, pigmentary, and atrophic autosomal recessive disease. It is manifested as an extreme photosensitivity to ULTRAVIOLET RAYS as the result of a deficiency in the enzyme that permits excisional repair of ultraviolet-damaged DNA.	3.85	12	0
Age-Related Memory Disorders [description not available]	2.13	1	0
Memory Disorders Disturbances in registering an impression, in the retention of an acquired impression, or in the recall of an impression. Memory impairments are associated with DEMENTIA; CRANIOCEREBRAL TRAUMA; ENCEPHALITIS; ALCOHOLISM (see also ALCOHOL AMNESTIC DISORDER); SCHIZOPHRENIA; and other conditions.	2.13	1	0
HPV Infection [description not available]	2.13	1	0
Papillomavirus Infections Neoplasms of the skin and mucous membranes caused by papillomaviruses. They are usually benign but some have a high risk for malignant progression.	2.13	1	0
Airway Hyper-Responsiveness [description not available]	2.13	1	0
Bradyarrhythmia [description not available]	2.13	1	0
Anasarca [description not available]	3.39	7	0
Bradycardia Cardiac arrhythmias that are characterized by excessively slow HEART RATE, usually below 50 beats per minute in human adults. They can be classified broadly into SINOATRIAL NODE dysfunction and ATRIOVENTRICULAR BLOCK.	2.13	1	0
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	8.39	7	0
Developmental Psychomotor Disorders [description not available]	2.13	1	0
Sterility, Male [description not available]	3	4	0
Infertility, Male The inability of the male to effect FERTILIZATION of an OVUM after a specified period of unprotected intercourse. Male sterility is permanent infertility.	3	4	0
Bowel Diseases, Inflammatory [description not available]	2.13	1	0
Inflammatory Bowel Diseases Chronic, non-specific inflammation of the GASTROINTESTINAL TRACT. Etiology may be genetic or environmental. This term includes CROHN DISEASE and ULCERATIVE COLITIS.	2.13	1	0
Fetal Resorption The disintegration and assimilation of the dead FETUS in the UTERUS at any stage after the completion of organogenesis which, in humans, is after the 9th week of GESTATION. It does not include embryo resorption (see EMBRYO LOSS).	2.69	3	0
Chronic Pancreatitis [description not available]	2.13	1	0
Pancreatitis, Chronic INFLAMMATION of the PANCREAS that is characterized by recurring or persistent ABDOMINAL PAIN with or without STEATORRHEA or DIABETES MELLITUS. It is characterized by the irregular destruction of the pancreatic parenchyma which may be focal, segmental, or diffuse.	2.13	1	0
Autoimmune Diabetes [description not available]	2.15	1	0
Diabetes Mellitus, Type 1 A subtype of DIABETES MELLITUS that is characterized by INSULIN deficiency. It is manifested by the sudden onset of severe HYPERGLYCEMIA, rapid progression to DIABETIC KETOACIDOSIS, and DEATH unless treated with insulin. The disease may occur at any age, but is most common in childhood or adolescence.	2.15	1	0
Fetal Growth Restriction [description not available]	2.47	2	0
Infant, Newborn, Diseases Diseases of newborn infants present at birth (congenital) or developing within the first month of birth. It does not include hereditary diseases not manifesting at birth or within the first 30 days of life nor does it include inborn errors of metabolism. Both HEREDITARY DISEASES and METABOLISM, INBORN ERRORS are available as general concepts.	2.13	1	0
Fetal Growth Retardation Failure of a FETUS to attain expected GROWTH.	2.47	2	0
Metaplasia A condition in which there is a change of one adult cell type to another similar adult cell type.	4.36	21	0
Tracheal Neoplasms New abnormal growth of tissue in the TRACHEA.	3.75	11	0
Lordosis The anterior concavity in the curvature of the lumbar and cervical spine as viewed from the side. The term usually refers to abnormally increased curvature (hollow back, saddle back, swayback). It does not include lordosis as normal mating posture in certain animals ( = POSTURE + SEX BEHAVIOR, ANIMAL).	2.04	1	0
Chylopericardium [description not available]	2.04	1	0
Pericardial Effusion Fluid accumulation within the PERICARDIUM. Serous effusions are associated with pericardial diseases. Hemopericardium is associated with trauma. Lipid-containing effusion (chylopericardium) results from leakage of THORACIC DUCT. Severe cases can lead to CARDIAC TAMPONADE.	2.04	1	0
Atypical Mycobacterial Infection, Disseminated [description not available]	2.05	1	0
Glial Cell Tumors [description not available]	2.04	1	0
Glioma Benign and malignant central nervous system neoplasms derived from glial cells (i.e., astrocytes, oligodendrocytes, and ependymocytes). Astrocytes may give rise to astrocytomas (ASTROCYTOMA) or glioblastoma multiforme (see GLIOBLASTOMA). Oligodendrocytes give rise to oligodendrogliomas (OLIGODENDROGLIOMA) and ependymocytes may undergo transformation to become EPENDYMOMA; CHOROID PLEXUS NEOPLASMS; or colloid cysts of the third ventricle. (From Escourolle et al., Manual of Basic Neuropathology, 2nd ed, p21)	2.04	1	0
Nicotine Addiction [description not available]	3.37	2	0
Tobacco Use Disorder Tobacco used to the detriment of a person's health or social functioning. Tobacco dependence is included.	3.37	2	0
Multiple Primary Neoplasms [description not available]	3.08	5	0
Aortic Aneurysm, Ruptured [description not available]	2.04	1	0
Ischemia A hypoperfusion of the BLOOD through an organ or tissue caused by a PATHOLOGIC CONSTRICTION or obstruction of its BLOOD VESSELS, or an absence of BLOOD CIRCULATION.	2.44	2	0
Hay Fever [description not available]	2.71	3	0
Rhinitis, Allergic, Seasonal Allergic rhinitis that occurs at the same time every year. It is characterized by acute CONJUNCTIVITIS with lacrimation and ITCHING, and regarded as an allergic condition triggered by specific ALLERGENS.	2.71	3	0
Aortic Diseases Pathological processes involving any part of the AORTA.	2.41	2	0
Aggression Behavior which may be manifested by destructive and attacking action which is verbal or physical, by covert attitudes of hostility or by obstructionism.	2.05	1	0
Corynebacterium diphtheriae Infection [description not available]	2.05	1	0
Diphtheria A localized infection of mucous membranes or skin caused by toxigenic strains of CORYNEBACTERIUM DIPHTHERIAE. It is characterized by the presence of a pseudomembrane at the site of infection. DIPHTHERIA TOXIN, produced by C. diphtheriae, can cause myocarditis, polyneuritis, and other systemic toxic effects.	2.05	1	0
Testicular Diseases Pathological processes of the TESTIS.	2.05	1	0
Leukemia L5178 An experimental lymphocytic leukemia of mice.	5.31	7	2
Colonic Polyps Discrete tissue masses that protrude into the lumen of the COLON. These POLYPS are connected to the wall of the colon either by a stalk, pedunculus, or by a broad base.	2.98	4	0
Caries, Dental [description not available]	2.97	1	0
Parodontosis [description not available]	3.32	2	0
Dental Caries Localized destruction of the tooth surface initiated by decalcification of the enamel followed by enzymatic lysis of organic structures and leading to cavity formation. If left unchecked, the cavity may penetrate the enamel and dentin and reach the pulp.	2.97	1	0
Periodontal Diseases Pathological processes involving the PERIODONTIUM including the gum (GINGIVA), the alveolar bone (ALVEOLAR PROCESS), the DENTAL CEMENTUM, and the PERIODONTAL LIGAMENT.	3.32	2	0
Anesthesia A state characterized by loss of feeling or sensation. This depression of nerve function is usually the result of pharmacologic action and is induced to allow performance of surgery or other painful procedures.	7.05	1	0
Enteritis Inflammation of any segment of the SMALL INTESTINE.	2.05	1	0
Cell Transformation, Viral An inheritable change in cells manifested by changes in cell division and growth and alterations in cell surface properties. It is induced by infection with a transforming virus.	4.91	14	0
Embryopathies [description not available]	3.86	4	0
Abnormalities, Drug-Induced Congenital abnormalities caused by medicinal substances or drugs of abuse given to or taken by the mother, or to which she is inadvertently exposed during the manufacture of such substances. The concept excludes abnormalities resulting from exposure to non-medicinal chemicals in the environment.	4.68	11	0
Cervix Diseases [description not available]	2.05	1	0
Long Sleeper Syndrome [description not available]	2.06	1	0
Sleep Wake Disorders Abnormal sleep-wake schedule or pattern associated with the CIRCADIAN RHYTHM which affect the length, timing, and/or rigidity of the sleep-wake cycle relative to the day-night cycle.	2.06	1	0
Leukemia, Lymphoblastic, Acute, T Cell [description not available]	2.06	1	0
Precursor T-Cell Lymphoblastic Leukemia-Lymphoma A leukemia/lymphoma found predominately in children and young adults and characterized LYMPHADENOPATHY and THYMUS GLAND involvement. It most frequently presents as a lymphoma, but a leukemic progression in the bone marrow is common.	2.06	1	0
Newcastle Disease An acute febrile, contagious, viral disease of birds caused by an AVULAVIRUS called NEWCASTLE DISEASE VIRUS. It is characterized by respiratory and nervous symptoms in fowl and is transmissible to man causing a severe, but transient conjunctivitis.	2.06	1	0
Neoplasms, Squamous Cell Neoplasms of the SQUAMOUS EPITHELIAL CELLS. The concept does not refer to neoplasms located in tissue composed of squamous elements.	2.44	2	0
Dermatoses [description not available]	2.4	2	0
Skin Diseases Diseases involving the DERMIS or EPIDERMIS.	2.4	2	0
Femoral Fractures Fractures of the femur.	2.07	1	0
Segond Fracture [description not available]	2.07	1	0
Tibial Fractures Fractures of the TIBIA.	2.07	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.	4.51	24	0
Edema, Pulmonary [description not available]	2.07	1	0
Pulmonary Edema Excessive accumulation of extravascular fluid in the lung, an indication of a serious underlying disease or disorder. Pulmonary edema prevents efficient PULMONARY GAS EXCHANGE in the PULMONARY ALVEOLI, and can be life-threatening.	2.07	1	0
Alcohol Drinking Behaviors associated with the ingesting of ALCOHOLIC BEVERAGES, including social drinking.	3.27	6	0
Endocarditis, Loeffler [description not available]	2.06	1	0
Hypereosinophilic Syndrome A heterogeneous group of disorders with the common feature of prolonged eosinophilia of unknown cause and associated organ system dysfunction, including the heart, central nervous system, kidneys, lungs, gastrointestinal tract, and skin. There is a massive increase in the number of EOSINOPHILS in the blood, mimicking leukemia, and extensive eosinophilic infiltration of the various organs.	2.06	1	0
Adenocarcinoma Of Kidney [description not available]	2.99	1	0
Carcinoma, Renal Cell A heterogeneous group of sporadic or hereditary carcinoma derived from cells of the KIDNEYS. There are several subtypes including the clear cells, the papillary, the chromophobe, the collecting duct, the spindle cells (sarcomatoid), or mixed cell-type carcinoma.	2.99	1	0
Hyperlipemia [description not available]	2.44	2	0
Hyperlipidemias Conditions with excess LIPIDS in the blood.	2.44	2	0
Complications, Pregnancy [description not available]	2.41	2	0
FMR1-Related Primary Ovarian Insufficiency [description not available]	2.08	1	0
Primary Ovarian Insufficiency Cessation of ovarian function after MENARCHE but before the age of 40, without or with OVARIAN FOLLICLE depletion. It is characterized by the presence of OLIGOMENORRHEA or AMENORRHEA, elevated GONADOTROPINS, and low ESTRADIOL levels. It is a state of female HYPERGONADOTROPIC HYPOGONADISM. Etiologies include genetic defects, autoimmune processes, chemotherapy, radiation, and infections. The most commonly known genetic cause is the expansion of a CGG repeat to 55 to 199 copies in the 5' untranslated region in the X-linked FMR1 gene.	2.08	1	0
Abnormalities, Congenital [description not available]	2.89	4	0
Vaccinia The cutaneous and occasional systemic reactions associated with vaccination using smallpox (variola) vaccine.	2.01	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)	9.17	17	0
Acute-Phase Reaction An early local inflammatory reaction to insult or injury that consists of fever, an increase in inflammatory humoral factors, and an increased synthesis by hepatocytes of a number of proteins or glycoproteins usually found in the plasma.	2.01	1	0
Hepatoblastoma A malignant neoplasm occurring in young children, primarily in the liver, composed of tissue resembling embryonal or fetal hepatic epithelium, or mixed epithelial and mesenchymal tissues. (Stedman, 25th ed)	2.01	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.	5.99	19	0
Marasmus [description not available]	2.39	2	0
Protein-Energy Malnutrition The lack of sufficient energy or protein to meet the body's metabolic demands, as a result of either an inadequate dietary intake of protein, intake of poor quality dietary protein, increased demands due to disease, or increased nutrient losses.	2.39	2	0
Cancer of Testis [description not available]	1.93	1	0
Testicular Neoplasms Tumors or cancer of the TESTIS. Germ cell tumors (GERMINOMA) of the testis constitute 95% of all testicular neoplasms.	1.93	1	0
Actinic Reticuloid Syndrome [description not available]	1.93	1	0
Respiratory Tract Neoplasms New abnormal growth of tissue in the RESPIRATORY SYSTEM.	5.08	17	0
Carbon Tetrachloride Poisoning Poisoning that results from ingestion, injection, inhalation, or skin absorption of CARBON TETRACHLORIDE.	2.35	2	0
Cancer of Gallbladder [description not available]	1.93	1	0
Gallbladder Neoplasms Tumors or cancer of the gallbladder.	1.93	1	0
Neoplasm Regression, Spontaneous Disappearance of a neoplasm or neoplastic state without the intervention of therapy.	1.93	1	0
Anthracosilicosis A form of pneumoconiosis caused by inhalation of dust that contains both CARBON and crystalline SILICON DIOXIDE. These foreign matters induce fibrous nodule formation in the lung.	2.85	1	0
Reticulum Cell-Like Sarcoma, Yoshida [description not available]	1.93	1	0
Carcinoma 256, Walker A transplantable carcinoma of the rat that originally appeared spontaneously in the mammary gland of a pregnant albino rat, and which now resembles a carcinoma in young transplants and a sarcoma in older transplants. (Stedman, 25th ed)	2.65	3	0
Orphan Diseases Rare diseases that have not been well studied.	1.94	1	0
Retinal Degeneration A retrogressive pathological change in the retina, focal or generalized, caused by genetic defects, inflammation, trauma, vascular disease, or aging. Degeneration affecting predominantly the macula lutea of the retina is MACULAR DEGENERATION. (Newell, Ophthalmology: Principles and Concepts, 7th ed, p304)	1.94	1	0
Cancer of the Vagina [description not available]	1.94	1	0
Vaginal Neoplasms Tumors or cancer of the VAGINA.	1.94	1	0
Cyst [description not available]	1.94	1	0
Hyperplasia, Reactive Lymphoid [description not available]	2.02	1	0
Hematologic Malignancies [description not available]	2.02	1	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.	2.02	1	0
Alveolar Bone Atrophy [description not available]	2.02	1	0
Arteriosclerosis, Coronary [description not available]	2.02	1	0
Coronary Artery Disease Pathological processes of CORONARY ARTERIES that may derive from a congenital abnormality, atherosclerotic, or non-atherosclerotic cause.	2.02	1	0
Verruca [description not available]	2.02	1	0
Warts Benign epidermal proliferations or tumors; some are viral in origin.	2.02	1	0
Adverse Drug Event [description not available]	2.41	2	0
Drug-Related Side Effects and Adverse Reactions Disorders that result from the intended use of PHARMACEUTICAL PREPARATIONS. Included in this heading are a broad variety of chemically-induced adverse conditions due to toxicity, DRUG INTERACTIONS, and metabolic effects of pharmaceuticals.	2.41	2	0
Allergic Reaction [description not available]	2.42	2	0
Hypersensitivity Altered reactivity to an antigen, which can result in pathologic reactions upon subsequent exposure to that particular antigen.	2.42	2	0
Carcinoma, Intraepithelial [description not available]	3.1	5	0
Carcinoma in Situ A lesion with cytological characteristics associated with invasive carcinoma but the tumor cells are confined to the epithelium of origin, without invasion of the basement membrane.	3.1	5	0
Enlarged Spleen [description not available]	2.38	2	0
Anemia A reduction in the number of circulating ERYTHROCYTES or in the quantity of HEMOGLOBIN.	7.02	1	0
Bright Disease A historical classification which is no longer used. It described acute glomerulonephritis, acute nephritic syndrome, or acute nephritis. Named for Richard Bright.	2.02	1	0
Glomerulonephritis Inflammation of the renal glomeruli (KIDNEY GLOMERULUS) that can be classified by the type of glomerular injuries including antibody deposition, complement activation, cellular proliferation, and glomerulosclerosis. These structural and functional abnormalities usually lead to HEMATURIA; PROTEINURIA; HYPERTENSION; and RENAL INSUFFICIENCY.	2.02	1	0
Contact Dermatitis [description not available]	3.08	5	0
Dermatitis, Contact A type of acute or chronic skin reaction in which sensitivity is manifested by reactivity to materials or substances coming in contact with the skin. It may involve allergic or non-allergic mechanisms.	3.08	5	0
Biological Clock Disturbances [description not available]	2.43	2	0
Cadmium Poisoning Poisoning occurring after exposure to cadmium compounds or fumes. It may cause gastrointestinal syndromes, anemia, or pneumonitis.	3.3	2	0
Anemia, Hypoplastic [description not available]	2.68	3	0
Anemia, Aplastic A form of anemia in which the bone marrow fails to produce adequate numbers of peripheral blood elements.	2.68	3	0
Anxiety Neuroses [description not available]	2.02	1	0
Depression, Endogenous [description not available]	2.02	1	0
Anxiety Disorders Persistent and disabling ANXIETY.	2.02	1	0
Depressive Disorder An affective disorder manifested by either a dysphoric mood or loss of interest or pleasure in usual activities. The mood disturbance is prominent and relatively persistent.	2.02	1	0
Leucocythaemia [description not available]	3.33	2	0
Leukemia A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)	3.33	2	0
Alopecia Circumscripta [description not available]	2.03	1	0
Alopecia Areata Loss of scalp and body hair involving microscopically inflammatory patchy areas.	2.03	1	0
Leiomyosarcoma, Epithelioid [description not available]	2.69	3	0
Leiomyosarcoma A sarcoma containing large spindle cells of smooth muscle. Although it rarely occurs in soft tissue, it is common in the viscera. It is the most common soft tissue sarcoma of the gastrointestinal tract and uterus. The median age of patients is 60 years. (From Dorland, 27th ed; Holland et al., Cancer Medicine, 3d ed, p1865)	2.69	3	0
Chemical Sensitivities, Multiple [description not available]	2.95	1	0
Cancer, Second Primary [description not available]	2.03	1	0
Bleeding [description not available]	2.42	2	0
Hemorrhage Bleeding or escape of blood from a vessel.	2.42	2	0
Bilateral Nasal Obstruction [description not available]	2.03	1	0
Rhinitis, Allergic, Nonseasonal [description not available]	2.03	1	0
Rhinitis, Allergic, Perennial Inflammation of the mucous membrane of the nose similar to that found in hay fever except that symptoms persist throughout the year. The causes are usually air-borne allergens, particularly dusts, feathers, molds, animal fur, etc.	2.03	1	0
Nasal Obstruction Any hindrance to the passage of air into and out of the nose. The obstruction may be unilateral or bilateral, and may involve any part of the NASAL CAVITY.	2.03	1	0
Reproductive Sterility [description not available]	2.04	1	0
Infertility A reduced or absent capacity to reproduce.	2.04	1	0
Carcinoma, Bronchial [description not available]	3.98	5	0
Carcinoma, Bronchogenic Malignant neoplasm arising from the epithelium of the BRONCHI. It represents a large group of epithelial lung malignancies which can be divided into two clinical groups: SMALL CELL LUNG CANCER and NON-SMALL-CELL LUNG CARCINOMA.	3.98	5	0
Osteogenic Sarcoma [description not available]	2.37	2	0
Osteosarcoma A sarcoma originating in bone-forming cells, affecting the ends of long bones. It is the most common and most malignant of sarcomas of the bones, and occurs chiefly among 10- to 25-year-old youths. (From Stedman, 25th ed)	2.37	2	0
Menopause The last menstrual period. Permanent cessation of menses (MENSTRUATION) is usually defined after 6 to 12 months of AMENORRHEA in a woman over 45 years of age. In the United States, menopause generally occurs in women between 48 and 55 years of age.	2.36	2	0
Fibromatosis [description not available]	1.96	1	0
Fibroma A benign tumor of fibrous or fully developed connective tissue.	1.96	1	0
Experimental Leukemia [description not available]	3.21	6	0
Neoplasms, Nervous System [description not available]	1.96	1	0
Chromosomal Translocation [description not available]	2.67	3	0
Leukemia L 1210 [description not available]	1.95	1	0
Acne [description not available]	1.96	1	0
Acne Vulgaris A chronic disorder of the pilosebaceous apparatus associated with an increase in sebum secretion. It is characterized by open comedones (blackheads), closed comedones (whiteheads), and pustular nodules. The cause is unknown, but heredity and age are predisposing factors.	1.96	1	0
Cancer of Eye [description not available]	1.96	1	0
Avian Sarcoma [description not available]	2.36	2	0
Cancer of Pituitary [description not available]	1.96	1	0
Pituitary Neoplasms Neoplasms which arise from or metastasize to the PITUITARY GLAND. The majority of pituitary neoplasms are adenomas, which are divided into non-secreting and secreting forms. Hormone producing forms are further classified by the type of hormone they secrete. Pituitary adenomas may also be characterized by their staining properties (see ADENOMA, BASOPHIL; ADENOMA, ACIDOPHIL; and ADENOMA, CHROMOPHOBE). Pituitary tumors may compress adjacent structures, including the HYPOTHALAMUS, several CRANIAL NERVES, and the OPTIC CHIASM. Chiasmal compression may result in bitemporal HEMIANOPSIA.	1.96	1	0
Dysembryoma [description not available]	2.65	3	0
Teratoma A true neoplasm composed of a number of different types of tissue, none of which is native to the area in which it occurs. It is composed of tissues that are derived from three germinal layers, the endoderm, mesoderm, and ectoderm. They are classified histologically as mature (benign) or immature (malignant). (From DeVita Jr et al., Cancer: Principles & Practice of Oncology, 3d ed, p1642)	2.65	3	0
Deficiency of Glucose-6-Phosphate Dehydrogenase [description not available]	3.22	6	0
Glucosephosphate Dehydrogenase Deficiency A disease-producing enzyme deficiency subject to many variants, some of which cause a deficiency of GLUCOSE-6-PHOSPHATE DEHYDROGENASE activity in erythrocytes, leading to hemolytic anemia.	3.22	6	0
Carcinoma, Basal Cell, Pigmented [description not available]	2.66	3	0
Carcinoma, Basal Cell A malignant skin neoplasm that seldom metastasizes but has potentialities for local invasion and destruction. Clinically it is divided into types: nodular, cicatricial, morphaic, and erythematoid (pagetoid). They develop on hair-bearing skin, most commonly on sun-exposed areas. Approximately 85% are found on the head and neck area and the remaining 15% on the trunk and limbs. (From DeVita Jr et al., Cancer: Principles & Practice of Oncology, 3d ed, p1471)	2.66	3	0
Aneuploid [description not available]	3.59	9	0
Arrhythmia [description not available]	1.96	1	0
Arrhythmias, Cardiac Any disturbances of the normal rhythmic beating of the heart or MYOCARDIAL CONTRACTION. Cardiac arrhythmias can be classified by the abnormalities in HEART RATE, disorders of electrical impulse generation, or impulse conduction.	1.96	1	0
Deficiency, Vitamin K [description not available]	1.96	1	0
Vitamin K Deficiency A nutritional condition produced by a deficiency of VITAMIN K in the diet, characterized by an increased tendency to hemorrhage (HEMORRHAGIC DISORDERS). Such bleeding episodes may be particularly severe in newborn infants. (From Cecil Textbook of Medicine, 19th ed, p1182)	1.96	1	0
Infections, Listeria [description not available]	1.96	1	0
Cancer of Larynx [description not available]	4.28	7	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.	1.96	1	0
Laryngeal Neoplasms Cancers or tumors of the LARYNX or any of its parts: the GLOTTIS; EPIGLOTTIS; LARYNGEAL CARTILAGES; LARYNGEAL MUSCLES; and VOCAL CORDS.	4.28	7	0
Choline Deficiency A condition produced by a deficiency of CHOLINE in animals. Choline is known as a lipotropic agent because it has been shown to promote the transport of excess fat from the liver under certain conditions in laboratory animals. Combined deficiency of choline (included in the B vitamin complex) and all other methyl group donors causes liver cirrhosis in some animals. Unlike compounds normally considered as vitamins, choline does not serve as a cofactor in enzymatic reactions. (From Saunders Dictionary & Encyclopedia of Laboratory Medicine and Technology, 1984)	1.96	1	0
Deficiency, Vitamin A [description not available]	4.17	17	0
Vitamin A Deficiency A nutritional condition produced by a deficiency of VITAMIN A in the diet, characterized by NIGHT BLINDNESS and other ocular manifestations such as dryness of the conjunctiva and later of the cornea (XEROPHTHALMIA). Vitamin A deficiency is a very common problem worldwide, particularly in developing countries as a consequence of famine or shortages of vitamin A-rich foods. In the United States it is found among the urban poor, the elderly, alcoholics, and patients with malabsorption. (From Cecil Textbook of Medicine, 19th ed, p1179)	4.17	17	0
Carbon Monoxide Poisoning Toxic asphyxiation due to the displacement of oxygen from oxyhemoglobin by carbon monoxide.	2.88	1	0
Poisoning, Lead [description not available]	2.88	1	0
Bronchitis Inflammation of the large airways in the lung including any part of the BRONCHI, from the PRIMARY BRONCHI to the TERTIARY BRONCHI.	3.81	4	0
Lead Poisoning Poisoning that results from chronic or acute ingestion, injection, inhalation, or skin absorption of LEAD or lead compounds.	2.88	1	0
Herpes Simplex Virus Infection [description not available]	6.96	1	0
Herpes Simplex A group of acute infections caused by herpes simplex virus type 1 or type 2 that is characterized by the development of one or more small fluid-filled vesicles with a raised erythematous base on the skin or mucous membrane. It occurs as a primary infection or recurs due to a reactivation of a latent infection. (Dorland, 27th ed.)	6.96	1	0
Rhabdomyosarcoma A malignant solid tumor arising from mesenchymal tissues which normally differentiate to form striated muscle. It can occur in a wide variety of sites. It is divided into four distinct types: pleomorphic, predominantly in male adults; alveolar (RHABDOMYOSARCOMA, ALVEOLAR), mainly in adolescents and young adults; embryonal (RHABDOMYOSARCOMA, EMBRYONAL), predominantly in infants and children; and botryoidal, also in young children. It is one of the most frequently occurring soft tissue sarcomas and the most common in children under 15. (From Dorland, 27th ed; Holland et al., Cancer Medicine, 3d ed, p2186; DeVita Jr et al., Cancer: Principles & Practice of Oncology, 3d ed, pp1647-9)	2.66	3	0
Deficiency, Thiamine [description not available]	1.96	1	0
Thiamine Deficiency A nutritional condition produced by a deficiency of THIAMINE in the diet, characterized by anorexia, irritability, and weight loss. Later, patients experience weakness, peripheral neuropathy, headache, and tachycardia. In addition to being caused by a poor diet, thiamine deficiency in the United States most commonly occurs as a result of alcoholism, since ethanol interferes with thiamine absorption. In countries relying on polished rice as a dietary staple, BERIBERI prevalence is very high. (From Cecil Textbook of Medicine, 19th ed, p1171)	1.96	1	0
Absence of Brain, Congenital [description not available]	1.96	1	0
Hyperkyphosis [description not available]	1.96	1	0
Anochlesia [description not available]	1.96	1	0
Absence Seizure [description not available]	1.96	1	0
Seizures Clinical or subclinical disturbances of cortical function due to a sudden, abnormal, excessive, and disorganized discharge of brain cells. Clinical manifestations include abnormal motor, sensory and psychic phenomena. Recurrent seizures are usually referred to as EPILEPSY or seizure disorder.	1.96	1	0
Chromosome Deletion Actual loss of portion of a chromosome.	2.39	2	0
Carcinoma, Adenosquamous A mixed adenocarcinoma and squamous cell or epidermoid carcinoma.	1.98	1	0
Antibody Deficiency Syndrome [description not available]	1.98	1	0
Immunologic Deficiency Syndromes Syndromes in which there is a deficiency or defect in the mechanisms of immunity, either cellular or humoral.	1.98	1	0
Ear Diseases Pathological processes of the ear, the hearing, and the equilibrium system of the body.	1.98	1	0
Cancer of Digestive System [description not available]	1.98	1	0
Digestive System Neoplasms Tumors or cancer of the DIGESTIVE SYSTEM.	1.98	1	0
Leukocytopenia [description not available]	2.4	2	0
Leukopenia A decrease in the number of LEUKOCYTES in a blood sample below the normal range (LEUKOCYTE COUNT less than 4000).	2.4	2	0
B-Cell Lymphoma [description not available]	1.98	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.	1.98	1	0
Acute Promyelocytic Leukemia [description not available]	1.98	1	0
Leukemia, Promyelocytic, Acute An acute myeloid leukemia in which abnormal PROMYELOCYTES predominate. It is frequently associated with DISSEMINATED INTRAVASCULAR COAGULATION.	1.98	1	0
Cancer of Duodenum [description not available]	2.9	1	0
Adenoma, Villous An adenoma of the large intestine. It is usually a solitary, sessile, often large, tumor of colonic mucosa composed of mucinous epithelium covering delicate vascular projections. Hypersecretion and malignant changes occur frequently. (Stedman, 25th ed)	2.9	1	0
Bagassosis A diffuse parenchymal lung disease caused by inhaled dust from processing SUGARCANE (bagasse), usually in the manufacturing of wallboard.	2.38	2	0
Pneumoconiosis A diffuse parenchymal lung disease caused by inhalation of dust and by tissue reaction to their presence. These inorganic, organic, particulate, or vaporized matters usually are inhaled by workers in their occupational environment, leading to the various forms (ASBESTOSIS; BYSSINOSIS; and others). Similar air pollution can also have deleterious effects on the general population.	2.38	2	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.	2.38	2	0
ATLL [description not available]	1.98	1	0
Leukemia-Lymphoma, Adult T-Cell Aggressive T-Cell malignancy with adult onset, caused by HUMAN T-LYMPHOTROPIC VIRUS 1. It is endemic in Japan, the Caribbean basin, Southeastern United States, Hawaii, and parts of Central and South America and sub-Saharan Africa.	1.98	1	0
Crigler Najjar Syndrome [description not available]	1.98	1	0
Deficiency, Riboflavin [description not available]	1.98	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)	1.98	1	0
Carcinoma, Oat Cell [description not available]	2.9	4	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)	2.9	4	0
Gastritis Inflammation of the GASTRIC MUCOSA, a lesion observed in a number of unrelated disorders.	2.39	2	0
Neoplasms, Sebaceous Gland [description not available]	1.98	1	0
Gastric Diseases [description not available]	2.39	2	0
Bile Duct Obstruction [description not available]	1.98	1	0
Hepatitis, Animal INFLAMMATION of the LIVER in non-human animals.	1.98	1	0
Cholangitis Inflammation of the biliary ductal system (BILE DUCTS); intrahepatic, extrahepatic, or both.	1.98	1	0
Cholestasis Impairment of bile flow due to obstruction in small bile ducts (INTRAHEPATIC CHOLESTASIS) or obstruction in large bile ducts (EXTRAHEPATIC CHOLESTASIS).	1.98	1	0
Angioma, Sclerosing [description not available]	4.28	4	1
Abdominal Neoplasms New abnormal growth of tissue in the ABDOMEN.	3.78	2	1
Histiocytoma, Benign Fibrous A benign tumor composed, wholly or in part, of cells with the morphologic characteristics of HISTIOCYTES and with various fibroblastic components. Fibrous histiocytomas can occur anywhere in the body. When they occur in the skin, they are called dermatofibromas or sclerosing hemangiomas. (From DeVita Jr et al., Cancer: Principles & Practice of Oncology, 5th ed, p1747)	4.28	4	1
Hormone-Dependent Neoplasms [description not available]	2.91	1	0
Autosomal Chromosome Disorders [description not available]	2.4	2	0
Peritoneal Carcinomatosis [description not available]	2.68	3	0
Mesothelioma A tumor derived from mesothelial tissue (peritoneum, pleura, pericardium). It appears as broad sheets of cells, with some regions containing spindle-shaped, sarcoma-like cells and other regions showing adenomatous patterns. Pleural mesotheliomas have been linked to exposure to asbestos. (Dorland, 27th ed)	2.38	2	0
Peritoneal Neoplasms Tumors or cancer of the PERITONEUM.	2.68	3	0
Chromosomal Breakage [description not available]	1.99	1	0
Mouth Diseases Diseases involving the MOUTH.	2	1	0
Adenoma, Hepatocellular [description not available]	2	1	0
Neoplasms, Otorhinolaryngologic [description not available]	2	1	0
Keratoacanthoma A benign, non-neoplastic, usually self-limiting epithelial lesion closely resembling squamous cell carcinoma clinically and histopathologically. It occurs in solitary, multiple, and eruptive forms. The solitary and multiple forms occur on sunlight exposed areas and are identical histologically; they affect primarily white males. The eruptive form usually involves both sexes and appears as a generalized papular eruption.	2.68	3	0
Cancer of Oropharnyx [description not available]	2	1	0
Oropharyngeal Neoplasms Tumors or cancer of the OROPHARYNX.	2	1	0
Adenoma, Prostatic [description not available]	2	1	0
Prostatic Hyperplasia Increase in constituent cells in the PROSTATE, leading to enlargement of the organ (hypertrophy) and adverse impact on the lower urinary tract function. This can be caused by increased rate of cell proliferation, reduced rate of cell death, or both.	2	1	0
Cockayne Syndrome A syndrome characterized by multiple system abnormalities including DWARFISM; PHOTOSENSITIVITY DISORDERS; PREMATURE AGING; and HEARING LOSS. It is caused by mutations of a number of autosomal recessive genes encoding proteins that involve transcriptional-coupled DNA REPAIR processes. Cockayne syndrome is classified by the severity and age of onset. Type I (classical; CSA) is early childhood onset in the second year of life; type II (congenital; CSB) is early onset at birth with severe symptoms; type III (xeroderma pigmentosum; XP) is late childhood onset with mild symptoms.	2	1	0
Carcinoma, Giant Cell An epithelial neoplasm characterized by unusually large anaplastic cells. It is highly malignant with fulminant clinical course, bizarre histologic appearance and poor prognosis. It is most common in the lung and thyroid. (From Stedman, 25th ed & Segen, Dictionary of Modern Medicine, 1992)	2	1	0
Eczema, Atopic [description not available]	2	1	0
Dermatitis, Atopic A chronic inflammatory genetically determined disease of the skin marked by increased ability to form reagin (IgE), with increased susceptibility to allergic rhinitis and asthma, and hereditary disposition to a lowered threshold for pruritus. It is manifested by lichenification, excoriation, and crusting, mainly on the flexural surfaces of the elbow and knee. In infants it is known as infantile eczema.	2	1	0
Cancer of the Thymus [description not available]	1.94	1	0
Thymus Neoplasms Tumors or cancer of the THYMUS GLAND.	1.94	1	0
Schistosoma mansoni Infection [description not available]	7	1	0
Schistosomiasis mansoni Schistosomiasis caused by Schistosoma mansoni. It is endemic in Africa, the Middle East, South America, and the Caribbean and affects mainly the bowel, spleen, and liver.	2	1	0
Carcinoma, Transitional Cell A malignant neoplasm derived from TRANSITIONAL EPITHELIAL CELLS, occurring chiefly in the URINARY BLADDER; URETERS; or RENAL PELVIS.	2	1	0
Bronchial Hyperreactivity Tendency of the smooth muscle of the tracheobronchial tree to contract more intensely in response to a given stimulus than it does in the response seen in normal individuals. This condition is present in virtually all symptomatic patients with asthma. The most prominent manifestation of this smooth muscle contraction is a decrease in airway caliber that can be readily measured in the pulmonary function laboratory.	2	1	0
Hematuria Presence of blood in the urine.	2.01	1	0
Cytomegalic Inclusion Disease [description not available]	2.38	2	0
Cytomegalovirus Infections Infection with CYTOMEGALOVIRUS, characterized by enlarged cells bearing intranuclear inclusions. Infection may be in almost any organ, but the salivary glands are the most common site in children, as are the lungs in adults.	2.38	2	0
Granulomas [description not available]	2.37	2	0
Granuloma A relatively small nodular inflammatory lesion containing grouped mononuclear phagocytes, caused by infectious and noninfectious agents.	2.37	2	0
Ovarian Diseases Pathological processes of the OVARY.	2.38	2	0
Leukocytosis A transient increase in the number of leukocytes in a body fluid.	1.97	1	0
Thrombopenia [description not available]	1.97	1	0
Thrombocytopenia A subnormal level of BLOOD PLATELETS.	1.97	1	0
Silicosis A form of pneumoconiosis resulting from inhalation of dust containing crystalline form of SILICON DIOXIDE, usually in the form of quartz. Amorphous silica is relatively nontoxic.	2.37	2	0
Ataxia Telangiectasia Syndrome [description not available]	2.38	2	0
Ataxia Telangiectasia An autosomal recessive inherited disorder characterized by choreoathetosis beginning in childhood, progressive CEREBELLAR ATAXIA; TELANGIECTASIS of CONJUNCTIVA and SKIN; DYSARTHRIA; B- and T-cell immunodeficiency, and RADIOSENSITIVITY to IONIZING RADIATION. Affected individuals are prone to recurrent sinobronchopulmonary infections, lymphoreticular neoplasms, and other malignancies. Serum ALPHA-FETOPROTEINS are usually elevated. (Menkes, Textbook of Child Neurology, 5th ed, p688) The gene for this disorder (ATM) encodes a cell cycle checkpoint protein kinase and has been mapped to chromosome 11 (11q22-q23).	2.38	2	0
Asbestosis A form of pneumoconiosis caused by inhalation of asbestos fibers which elicit potent inflammatory responses in the parenchyma of the lung. The disease is characterized by interstitial fibrosis of the lung, varying from scattered sites to extensive scarring of the alveolar interstitium.	1.97	1	0
Cardiac Failure [description not available]	1.97	1	0
Heart Failure A heterogeneous condition in which the heart is unable to pump out sufficient blood to meet the metabolic need of the body. Heart failure can be caused by structural defects, functional abnormalities (VENTRICULAR DYSFUNCTION), or a sudden overload beyond its capacity. Chronic heart failure is more common than acute heart failure which results from sudden insult to cardiac function, such as MYOCARDIAL INFARCTION.	1.97	1	0
Genetic Diseases [description not available]	1.97	1	0
Genetic Diseases, Inborn Diseases that are caused by genetic mutations present during embryo or fetal development, although they may be observed later in life. The mutations may be inherited from a parent's genome or they may be acquired in utero.	1.97	1	0
Dermatitis, Occupational A recurrent contact dermatitis caused by substances found in the work place.	1.97	1	0
Inhalation Injury, Smoke [description not available]	2.89	1	0
Nutritional Disorders [description not available]	1.97	1	0
Nutrition Disorders Disorders caused by nutritional imbalance, either overnutrition or undernutrition.	1.97	1	0
Fetal Death Death of the developing young in utero. BIRTH of a dead FETUS is STILLBIRTH.	2.66	3	0
Adenocarcinoma, Alveolar [description not available]	1.97	1	0
Adenocarcinoma, Bronchiolo-Alveolar A carcinoma derived from epithelium of terminal bronchioles, in which the neoplastic tissue extends along the alveolar walls and grows in small masses within the alveoli. Involvement may be uniformly diffuse and massive, or nodular, or lobular. The neoplastic cells are cuboidal or columnar and form papillary structures. Mucin may be demonstrated in some of the cells and in the material in the alveoli, which also includes denuded cells. Metastases in regional lymph nodes, and in even more distant sites, are known to occur, but are infrequent. (From Stedman, 25th ed)	1.97	1	0
Neoplasms, Pleural [description not available]	1.97	1	0
Cholangioma [description not available]	1.97	1	0
Adenoma, Bile Duct A benign tumor of the intrahepatic bile ducts.	1.97	1	0
Fibroma, Shope [description not available]	1.96	1	0
Peritoneal Diseases Pathological processes involving the PERITONEUM.	1.96	1	0
Hypertrophy General increase in bulk of a part or organ due to CELL ENLARGEMENT and accumulation of FLUIDS AND SECRETIONS, not due to tumor formation, nor to an increase in the number of cells (HYPERPLASIA).	1.97	1	0
Cancer of Pharynx [description not available]	1.96	1	0
Pharyngeal Neoplasms Tumors or cancer of the PHARYNX.	1.96	1	0
Neuroma A tumor made up of nerve cells and nerve fibers. (Dorland, 27th ed)	1.97	1	0
Bleb [description not available]	1.96	1	0
Leukemia P388 An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.	1.97	1	0
Acute Myelogenous Leukemia [description not available]	1.96	1	0
Leukemia, Myeloid, Acute Clonal expansion of myeloid blasts in bone marrow, blood, and other tissue. Myeloid leukemias develop from changes in cells that normally produce NEUTROPHILS; BASOPHILS; EOSINOPHILS; and MONOCYTES.	1.96	1	0
Anemia, Hypochromic Anemia characterized by a decrease in the ratio of the weight of hemoglobin to the volume of the erythrocyte, i.e., the mean corpuscular hemoglobin concentration is less than normal. The individual cells contain less hemoglobin than they could have under optimal conditions. Hypochromic anemia may be caused by iron deficiency from a low iron intake, diminished iron absorption, or excessive iron loss. It can also be caused by infections or other diseases, therapeutic drugs, lead poisoning, and other conditions. (Stedman, 25th ed; from Miale, Laboratory Medicine: Hematology, 6th ed, p393)	1.96	1	0
Delayed Hypersensitivity [description not available]	1.96	1	0
Alcohol Abuse [description not available]	2.37	2	0
Alcoholism A primary, chronic disease with genetic, psychosocial, and environmental factors influencing its development and manifestations. The disease is often progressive and fatal. It is characterized by impaired control over drinking, preoccupation with the drug alcohol, use of alcohol despite adverse consequences, and distortions in thinking, most notably denial. Each of these symptoms may be continuous or periodic. (Morse & Flavin for the Joint Commission of the National Council on Alcoholism and Drug Dependence and the American Society of Addiction Medicine to Study the Definition and Criteria for the Diagnosis of Alcoholism: in JAMA 1992;268:1012-4)	2.37	2	0
Blastocyst Disintegration [description not available]	1.96	1	0
Hypospermatogenesis [description not available]	1.96	1	0
Inborn Errors of Metabolism [description not available]	1.96	1	0
Metabolism, Inborn Errors Errors in metabolic processes resulting from inborn genetic mutations that are inherited or acquired in utero.	1.96	1	0

benzo(a)pyrene

Description

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Synonyms (122)

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Toxicity

Pharmacokinetics

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Dosage Studied

Roles (2)

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Protein Targets (54)

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Ceullar Components (58)

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Research Demand Index: 65.24

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