alpha-naphthoflavone profile

Alpha-naphthoflavone (α-NF) is a synthetic polycyclic aromatic hydrocarbon that is a potent inducer of the aryl hydrocarbon receptor (AhR). It is widely used as a research tool to study the role of the AhR in various cellular processes, including detoxification, inflammation, and immune responses. α-NF is synthesized through a multi-step process involving Friedel-Crafts acylation, followed by a series of cyclizations and dehydrations. Its effects are primarily mediated through activation of the AhR, leading to the expression of a variety of genes involved in xenobiotic metabolism, including cytochrome P450 enzymes. It is a powerful inhibitor of certain cytochrome P450 enzymes, such as CYP1A1 and CYP1B1, which are involved in the metabolism of a wide range of compounds, including carcinogens. This inhibitory effect has led to its use in various studies investigating the role of these enzymes in drug metabolism, toxicity, and cancer development. α-NF is also studied for its potential therapeutic applications, such as its ability to inhibit angiogenesis and tumor growth in various cancer models. Its importance lies in its ability to elucidate the complex roles of the AhR in various physiological and pathological processes.'

alpha-naphthoflavone: inhibits P4501A1 and P4501A2; stimulates some activities of P4503A4 [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

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). [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	11790
CHEMBL ID	283196
CHEBI ID	76995
SCHEMBL ID	121594
MeSH ID	M0057860

Synonym
BIDD:ER0569
5-17-10-00726 (beilstein handbook reference)
unii-fml65d8py5
fml65d8py5 ,
2-phenyl-benzo[h]chromen-4-one
2-phenylbenzo[h]chromen-4-one
4h-naphtho[1,2-b]pyran-4-one, 2-phenyl-
BHF ,
2-phenyl-4h-benzo[h]chromen-4-one
2-phenylbenzo(h)chromen-4-one
nsc 407011
ccris 3607
benzo(h)flavone
2-phenyl-4h-naphtho(1,2-b)pyran-4-one
einecs 210-071-1
4h-naphtho(1,2-b)pyran-4-one, 2-phenyl-
brn 0210862
alpha-naphthylflavone
OPREA1_802803
tnp00080
NCGC00017210-01
.alpha.-naphthylflavone
nsc407011
604-59-1
nsc-407011
mls003171601 ,
4h-naphtho[1, 2-phenyl-
7,8-bf
.alpha.-naphthoflavone
7,8-benzoflavone
OPREA1_054595
NCGC00142408-01
N-1500
alpha-naphthoflavone
B0056
CHEMBL283196 ,
chebi:76995 ,
alpha-naphtholflavone
alpha-naphtoflavone
AKOS000505579
DB07453
bdbm50014323
2-phenyl-4-benzo[h][1]benzopyranone
A832737
smr000112233
NCGC00017210-02
FT-0622183
benzo[h]flavone
methyl3-(2,5-dimethyl-1h-pyrrol-1-yl)-2-thiophenecarboxylate
SCHEMBL121594
naphthoflavon
2-phenyl-4h-benzo[h]chromen-4-one #
PS-7270
mfcd00004985
DTXSID2040650
7,8-benzoflavone; alpha-naphthoflavone
Q4734915
F16466
a-naphthylflavone
CS-W014028
HMS3740O15
HY-125833
CCG-267182
benzoflavone, 7,8-
ccris-3607
2-phenyl-4h-benzo(h)chromen-4-one
S5158
SY012881
alpha -naphthoflavone
EN300-122288

Excerpt	Reference	Relevance
" The 2-MeOE2 metabolite followed by 2-OHE2 and E2 (in this order) proved to be extremely toxic to dividing MCF-7 and HeLa cells."	( The cytotoxic effects of estradiol-17 beta, catecholestradiols and methoxyestradiols on dividing MCF-7 and HeLa cells. Aveling, ML; Cross, M; Joubert, WS; Koch, F; Seegers, JC; Van Aswegen, CH, 1989)	0.28
" At the highest concentration of ANF, retene toxicity was eliminated, and parent retene was the predominant form in tissue; no concentration of ANF was toxic by itself."	( Inhibition of CYP1A enzymes by alpha-naphthoflavone causes both synergism and antagonism of retene toxicity to rainbow trout (Oncorhynchus mykiss). Akhtar, P; Brown, RS; Hodson, PV; Noble, CA; Qureshi, K, 2007)	0.63
"Isoline, a major retronecine-type pyrrolizidine alkaloid (PA) from the Chinese medicinal herb Ligularia duciformis, was suggested to be the most toxic known PA."	( In vitro metabolism of isoline, a pyrrolizidine alkaloid from Ligularia duciformis, by rodent liver microsomal esterase and enhanced hepatotoxicity by esterase inhibitors. Akao, T; Hattori, M; Nakamura, N; Sasahara, M; Takagawa, K; Tang, J; Wang, ZT, 2007)	0.34
" These findings suggest that HepG2 cells were more sensitive to the cytotoxicity of ginkgolic acid than primary rat hepatocytes, and CYP1A and CYP3A could metabolize ginkgolic acid to more toxic compounds."	( Cytotoxicity of ginkgolic acid in HepG2 cells and primary rat hepatocytes. Liu, ZH; Zeng, S, 2009)	0.35
" These data demonstrate that the parent forms of leflunomide and A77 1726 are more toxic to hepatocytes than their poorly characterized metabolites, indicating that the metabolic process of leflunomide is a detoxification step rather than an initiating event leading to toxicity."	( Hepatic cytochrome P450s attenuate the cytotoxicity induced by leflunomide and its active metabolite A77 1726 in primary cultured rat hepatocytes. Greenhaw, J; Salminen, WF; Shi, Q; Yang, X, 2011)	0.37
" These data demonstrate that UA is bio-transformed to less toxic metabolites in rat primary hepatocytes, probably mainly by CYP1A and 3A, but not 2B/2C."	( Inhibition of cytochrome P450s enhances (+)-usnic acid cytotoxicity in primary cultured rat hepatocytes. Greenhaw, J; Salminen, WF; Shi, Q, 2014)	0.4
" Cytotoxicity of ANF hydrosol was examined to get an idea of the toxic level of this hydrosol toward cultured normal human cells."	( Aggregation induced emission from α-napthoflavone microstructures and its cyto-toxicity. Chattopadhyay, D; Das, D; Maity, A; Mazumdar, P; Misra, A; Roy, S; Tripathy, S, 2016)	0.43
" Retene (7-isopropyl-1-methylphenanthrene), a typical alkyl-phenanthrene compound, can be more toxic than phenanthrene, and the mechanism of retene toxicity is likely related to its rapid biotransformation by cytochrome P450 (CYP) enzymes to metabolites with a wide array of structures and potential toxicities."	( The effects of CYP1A inhibition on alkyl-phenanthrene metabolism and embryotoxicity in marine medaka (Oryzias melastigma). Cong, Y; Jin, F; Mu, J; Wang, J; Wang, Y, 2016)	0.43
"Amiodarone is a widely used potent antiarrhythmic for the treatment of cardiac disease; however, its use is often discontinued due to numerous adverse effects, including hepatotoxicity."	( The role of CYP 3A4 and 1A1 in amiodarone-induced hepatocellular toxicity. Bryant, MS; Guo, L; Ning, B; Ren, Z; Wu, Q; Xuan, J, 2016)	0.43
" However, tacrine was removed from the market due to its hepatotoxicity concerns as it undergoes metabolism to toxic quinonemethide species through the cytochrome P450 enzyme CYP1A2."	( Cytochrome P450 binding studies of novel tacrine derivatives: Predicting the risk of hepatotoxicity. Edginton, AN; McEneny-King, A; Osman, W; Rao, PPN, 2017)	0.46

Excerpt	Reference	Relevance
" Pharmacokinetic analysis was conducted by WinNonlin and ADAPT II."	( Pharmacokinetics and bioavailability of the flavonoid 7,8-benzoflavone in rats. Morris, ME; Wang, X, 2008)	0.35

Excerpt	Reference	Relevance
" 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 objective of this study was to investigate the pharmacokinetics and bioavailability of 7,8-benzoflavone in rats."	( Pharmacokinetics and bioavailability of the flavonoid 7,8-benzoflavone in rats. Morris, ME; Wang, X, 2008)	0.35
" This study focused on the bioavailability of PAHs and on the tumor initiation potential of wood combustion PM, using the PAH CALUX® reporter gene assay and the BALB/c 3T3 cell transformation assay, respectively."	( Bioavailability and potential carcinogenicity of polycyclic aromatic hydrocarbons from wood combustion particulate matter in vitro. Dietrich, DR; Gauggel-Lewandowski, S; Heussner, AH; Pieterse, B; Steinberg, P; van der Burg, B, 2013)	0.39

Excerpt	Relevance	Reference
" In contrast, the dose-response curve for methylation by NDMA appeared opposite of that for NNK with alkylation efficiency increasing as a function of dose."	( Factors regulating activation and DNA alkylation by 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone and nitrosodimethylamine in rat lung and isolated lung cells, and the relationship to carcinogenicity. Anderson, MW; Belinsky, SA; Devereux, TR, 1988)	0.27
" Significant dose-response relationships were found between the frequency of SCEs and factors related to smoking, such as duration and frequency of cigarette use, tar, nicotine, carbon monoxide content of brand, and urinary measures of nicotine metabolites (cotinine and thiocyanate)."	( Effects of alpha-naphthoflavone on levels of sister chromatid exchanges in lymphocytes from active and passive cigarette smokers: dose-response relationships. Collman, GW; Lucier, GW; Lundgren, K; Shore, D; Thompson, CL, 1986)	0.66
" The 3-methylcholanthrene-dependent increases in 2- and 3-hydroxylation appear due to induction of a single form of cytochrome P-450, as indicated by similar dose-response relationships and similar changes in sensitivity to the inhibitors."	( Biphenyl metabolism by rat liver microsomes: regioselective effects of inducers, inhibitors, and solvents. Haugen, DA, )	0.13
" Dose-response experiments and residue analysis data indicated that residues of commercial PCB mixtures were at least partially responsible for the effects described here."	( Xenobiotics in gametes of Lake Michigan lake trout (Salvelinus namaycush) induce hepatic monooxygenase activity in their offspring. Binder, RL; Lech, JJ, 1984)	0.27
" The beneficial effect of MET-TS therapy reported in a previous study (AFB2 dosage of 4 mg/kg) was not observed with the 3 mg/kg lethal dose."	( Effect of some enzyme inducers, fluids, and methionine-thiosulfate on induced acute aflatoxicosis in goats. Clark, JD; Hatch, RC; Jain, AV; Mahaffey, EA; Weiss, R, 1982)	0.26
" Regardless of the presence or absence of 7,8-benzoflavone (ANF) in the blood culture system, we could observe a fairly good dose-response relationship between the concentration of the mixture of organochlorine compounds and the induction of SCEs/cell."	( Effects of highly toxic organochlorine compounds retained in human body on induction of sister chromatid exchanges in cultured human lymphocytes. Hirakawa, H; Iida, T; Masuda, Y; Matsueda, T; Nagayama, J; Nagayama, M, )	0.13
"Repeated dosing with the occupational chemical 4-vinylcyclohexene diepoxide (VCD) selectively depletes small pre-antral follicles in the ovaries of rats and mice via apoptosis."	( Differences between rats and mice in the involvement of the aryl hydrocarbon receptor in 4-vinylcyclohexene diepoxide-induced ovarian follicle loss. Benedict, JC; Bourguet, SM; Christian, PJ; Flaws, JA; Hoyer, PB; Sipes, IG; Thompson, KE, 2005)	0.33
" NFĸB activation elicited by IDM was suppressed by α-NF in a dose-response manner."	( α-Naphthoflavone modulates inflammatory response in adipocytes-macrophages interaction through NFκB signaling. Fan, C; Huang, T; Lei, S; Shi, Q; Sun, Y; Wang, S; Xie, M; Zhang, J; Zhang, X, 2014)	0.4
" For FA treatment, TCDD-treated mice were also dosed with 5, 10, and 15 mg/kg FA on GD 10, while for α-naphthoflavone treatment, the mice received a single dose of 50 μg/kg or 5 mg/kg α-naphthoflavone on GD 10."	( Comparative Study of Folic Acid and α-Naphthoflavone on Reducing TCDD-Induced Cleft Palate in Fetal Mice. Fu, Y; He, X; Liu, C; Pu, W; Qiu, L; Wang, C; Yuan, X; Zhang, X, 2017)	0.46

Role	Description
EC 1.14.14.14 (aromatase) inhibitor	An EC 1.14.14.* (oxidoreductase acting on paired donors, incorporating of 1 atom of oxygen, with reduced flavin or flavoprotein as one donor) inhibitor which interferes with the action of aromatase (EC 1.14.14.14) and so reduces production of estrogenic steroid hormones.
aryl hydrocarbon receptor antagonist	An antagonist that binds to and activates aryl hydrocarbon receptors (AhRs).
aryl hydrocarbon receptor agonist	An agonist that binds to and activates aryl hydrocarbon receptors (AhRs).
[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
organic heterotricyclic compound	An organic tricyclic compound in which at least one of the rings of the tricyclic skeleton contains one or more heteroatoms.
extended flavonoid	Any flavonoid with one or more rings fused on to the phenyl substituted benzopyran framework.
naphtho-gamma-pyrone	Any naphthopyran whose skeleton consists of a naphathalene ring system ortho-fused to a gamma-pyrone.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Chain A, HADH2 protein	Homo sapiens (human)	Potency	35.7168	0.0251	20.2376	39.8107	AID886; AID893
Chain B, HADH2 protein	Homo sapiens (human)	Potency	35.7168	0.0251	20.2376	39.8107	AID886; AID893
Chain A, 2-oxoglutarate Oxygenase	Homo sapiens (human)	Potency	35.4813	0.1778	14.3909	39.8107	AID2147
Chain A, Cruzipain	Trypanosoma cruzi	Potency	39.8107	0.0020	14.6779	39.8107	AID1476
phosphopantetheinyl transferase	Bacillus subtilis	Potency	44.6684	0.1413	37.9142	100.0000	AID1490
TDP1 protein	Homo sapiens (human)	Potency	8.4144	0.0008	11.3822	44.6684	AID686978
Microtubule-associated protein tau	Homo sapiens (human)	Potency	17.7828	0.1800	13.5574	39.8107	AID1460
aldehyde dehydrogenase 1 family, member A1	Homo sapiens (human)	Potency	31.6228	0.0112	12.4002	100.0000	AID1030
thyroid stimulating hormone receptor	Homo sapiens (human)	Potency	31.6228	0.0013	18.0743	39.8107	AID926; AID938
glucocerebrosidase	Homo sapiens (human)	Potency	31.6228	0.0126	8.1569	44.6684	AID2101
alpha-galactosidase	Homo sapiens (human)	Potency	7.0795	4.4668	18.3916	35.4813	AID1467
cytochrome P450 2D6 isoform 1	Homo sapiens (human)	Potency	12.5893	0.0020	7.5337	39.8107	AID891
cellular tumor antigen p53 isoform a	Homo sapiens (human)	Potency	31.6228	0.3162	12.4435	31.6228	AID902
cytochrome P450 2C19 precursor	Homo sapiens (human)	Potency	1.9953	0.0025	5.8400	31.6228	AID899
cytochrome P450 2C9 precursor	Homo sapiens (human)	Potency	7.9433	0.0063	6.9043	39.8107	AID883
15-hydroxyprostaglandin dehydrogenase [NAD(+)] isoform 1	Homo sapiens (human)	Potency	14.1254	0.0018	15.6638	39.8107	AID894
mitogen-activated protein kinase 1	Homo sapiens (human)	Potency	31.6228	0.0398	16.7842	39.8107	AID995
cytochrome P450 3A4 isoform 1	Homo sapiens (human)	Potency	12.5893	0.0316	10.2792	39.8107	AID884; AID885
lethal factor (plasmid)	Bacillus anthracis str. A2012	Potency	25.1189	0.0200	10.7869	31.6228	AID912
Gamma-aminobutyric acid receptor subunit pi	Rattus norvegicus (Norway rat)	Potency	12.5893	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit beta-1	Rattus norvegicus (Norway rat)	Potency	12.5893	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit delta	Rattus norvegicus (Norway rat)	Potency	12.5893	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit gamma-2	Rattus norvegicus (Norway rat)	Potency	12.5893	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit alpha-5	Rattus norvegicus (Norway rat)	Potency	12.5893	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit alpha-3	Rattus norvegicus (Norway rat)	Potency	12.5893	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit gamma-1	Rattus norvegicus (Norway rat)	Potency	12.5893	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit alpha-2	Rattus norvegicus (Norway rat)	Potency	12.5893	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit alpha-4	Rattus norvegicus (Norway rat)	Potency	12.5893	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit gamma-3	Rattus norvegicus (Norway rat)	Potency	12.5893	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit alpha-6	Rattus norvegicus (Norway rat)	Potency	12.5893	1.0000	12.2248	31.6228	AID885
Histamine H2 receptor	Cavia porcellus (domestic guinea pig)	Potency	7.9433	0.0063	8.2350	39.8107	AID883
Gamma-aminobutyric acid receptor subunit alpha-1	Rattus norvegicus (Norway rat)	Potency	12.5893	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit beta-3	Rattus norvegicus (Norway rat)	Potency	12.5893	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit beta-2	Rattus norvegicus (Norway rat)	Potency	12.5893	1.0000	12.2248	31.6228	AID885
GABA theta subunit	Rattus norvegicus (Norway rat)	Potency	12.5893	1.0000	12.2248	31.6228	AID885
Gamma-aminobutyric acid receptor subunit epsilon	Rattus norvegicus (Norway rat)	Potency	12.5893	1.0000	12.2248	31.6228	AID885
[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)
Carboxylic ester hydrolase	Sus scrofa (pig)	IC50 (µMol)	0.0478	0.0478	0.0478	0.0478	AID1437052
cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)	IC50 (µMol)	2.3034	0.0000	1.1843	9.6140	AID625167
Cytochrome P450 1A1	Homo sapiens (human)	IC50 (µMol)	2.4555	0.0079	1.2478	9.9000	AID1203555; AID1203557; AID1368049; AID1368058; AID1372144; AID1372149; AID1372158; AID1387231; AID1441872; AID1441877; AID1446923; AID1446934; AID1446936; AID1446940; AID1452981; AID1488356; AID1488363; AID1515295; AID1533283; AID1537805; AID1581701; AID1680601; AID1680603; AID1727621; AID311073; AID739410
Cytochrome P450 1A1	Homo sapiens (human)	Ki	0.0450	0.0120	0.9469	3.8000	AID1239148
Cytochrome P450 1A2	Homo sapiens (human)	IC50 (µMol)	2.1195	0.0001	1.7740	10.0000	AID1164253; AID1181450; AID1203554; AID1203558; AID1310919; AID1368051; AID1368060; AID1372146; AID1372151; AID1441873; AID1441878; AID1446925; AID1450067; AID1452984; AID1488358; AID1515296; AID1533284; AID1537806; AID1581702; AID1688848; AID1721034; AID1727622; AID1739435; AID1773465; AID1781975; AID1811055; AID1813639; AID1822287; AID1863226; AID1880382; AID1886458; AID1895931; AID1898236; AID1901573; AID311074; AID517524; AID625245; AID739409
Cytochrome P450 1A2	Homo sapiens (human)	Ki	0.0200	0.0056	1.1534	9.0000	AID1239149
ATP-dependent translocase ABCB1	Homo sapiens (human)	IC50 (µMol)	24.6000	0.0002	2.3185	10.0000	AID768684
Cytochrome P450 3A4	Homo sapiens (human)	IC50 (µMol)	13.3333	0.0001	1.7536	10.0000	AID1368055; AID1368064; AID1372147; AID1372152; AID1446927; AID1488362
Cytochrome P450 2D6	Homo sapiens (human)	IC50 (µMol)	13.3333	0.0000	2.0151	10.0000	AID1368052; AID1368061; AID1372148; AID1372153; AID1446926; AID1488359
Cytochrome P450 2A6	Homo sapiens (human)	IC50 (µMol)	25.0000	0.0044	3.8895	10.0000	AID739398
Aromatase	Homo sapiens (human)	IC50 (µMol)	1.0350	0.0000	1.2904	10.0000	AID321164; AID479369
Aromatase	Homo sapiens (human)	Ki	0.0200	0.0000	0.6046	9.5010	AID53739
Cytochrome P450 2C9	Homo sapiens (human)	IC50 (µMol)	15.0000	0.0000	2.8005	10.0000	AID1368053; AID1368062; AID1446928; AID1488360
UDP-glucuronosyltransferase 2B7	Homo sapiens (human)	IC50 (µMol)	115.4000	0.1000	2.5000	4.9000	AID1802994
UDP-glucuronosyltransferase 1-6	Homo sapiens (human)	IC50 (µMol)	115.4000	4.9000	4.9000	4.9000	AID1802994
Cytochrome P450 2B6	Homo sapiens (human)	IC50 (µMol)	13.0000	0.0011	3.4186	10.0000	AID739397
Substance-K receptor	Homo sapiens (human)	IC50 (µMol)	5.8471	0.0001	3.1210	9.5530	AID625227
Substance-K receptor	Homo sapiens (human)	Ki	1.9490	0.0001	1.9242	9.7930	AID625227
UDP-glucuronosyltransferase 1A1	Homo sapiens (human)	IC50 (µMol)	115.4000	0.3000	3.2580	7.3000	AID1802994
UDP-glucuronosyltransferase 1A4	Homo sapiens (human)	IC50 (µMol)	115.4000	4.7200	4.8100	4.9000	AID1802994
Sodium-dependent dopamine transporter	Rattus norvegicus (Norway rat)	IC50 (µMol)	0.0100	0.0007	0.9774	9.7000	AID1372144
Thromboxane-A synthase	Homo sapiens (human)	IC50 (µMol)	6.7608	0.0009	1.2304	10.0000	AID625229
Adenosine receptor A1	Homo sapiens (human)	IC50 (µMol)	1.1325	0.0002	0.6818	7.7010	AID625194
Adenosine receptor A1	Homo sapiens (human)	Ki	0.6606	0.0002	0.9316	10.0000	AID625194
Aryl hydrocarbon receptor	Mus musculus (house mouse)	IC50 (µMol)	0.0250	0.0210	0.0230	0.0250	AID1527834
Sodium-dependent serotonin transporter	Rattus norvegicus (Norway rat)	IC50 (µMol)	0.0500	0.0003	0.8197	8.4900	AID1372145
Cytochrome P450 2C19	Homo sapiens (human)	IC50 (µMol)	15.0000	0.0000	2.3983	10.0000	AID1368054; AID1368063; AID1446929; AID1488361
Multidrug resistance-associated protein 1	Homo sapiens (human)	IC50 (µMol)	11.3000	0.0015	3.7110	9.6600	AID768683
UDP-glucuronosyltransferase 2B10	Homo sapiens (human)	IC50 (µMol)	115.4000	4.9000	4.9000	4.9000	AID1802994
DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)	IC50 (µMol)	4.9800	0.0005	1.3500	10.0000	AID241691
Xanthine dehydrogenase/oxidase	Bos taurus (cattle)	IC50 (µMol)	20.0000	0.0030	3.1015	9.8000	AID1637837
Cytochrome P450 1B1	Homo sapiens (human)	IC50 (µMol)	10.8787	0.0013	0.8696	9.9000	AID1203553; AID1203556; AID1203565; AID1203566; AID1337729; AID1368050; AID1368059; AID1372145; AID1372150; AID1372154; AID1387230; AID1441864; AID1441865; AID1441870; AID1441871; AID1441876; AID1446924; AID1446935; AID1446937; AID1446941; AID1452980; AID1452987; AID1488357; AID1488364; AID1504638; AID1515294; AID1533285; AID1537804; AID1581700; AID1680600; AID1680602; AID1688847; AID1727620; AID311072
Cytochrome P450 1B1	Homo sapiens (human)	Ki	0.0160	0.0030	0.9741	7.4600	AID1239150
Histamine H3 receptor	Cavia porcellus (domestic guinea pig)	IC50 (µMol)	20.0000	0.0010	2.9070	8.6900	AID1637837
Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)	IC50 (µMol)	1.3550	0.0040	1.9666	10.0000	AID768689; AID768691
[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)
Cytochrome P450 1A1	Homo sapiens (human)	EC50 (µMol)	2.5000	1.8000	4.6000	8.8000	AID1372157; AID1411748
Cytochrome P450 1B1	Homo sapiens (human)	EC50 (µMol)	26.7000	1.1000	3.1000	5.1000	AID1372156; AID1441859; AID1441868
[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)
Cytochrome P450 1B1	Homo sapiens (human)	Ks	0.7000	0.7000	0.7000	0.7000	AID1515301
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
positive regulation of cardiac muscle hypertrophy	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
regulation of nitric oxide mediated signal transduction	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
T cell proliferation	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
negative regulation of T cell proliferation	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
cGMP catabolic process	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
oocyte development	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
negative regulation of cardiac muscle contraction	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
relaxation of cardiac muscle	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
positive regulation of oocyte development	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
cAMP-mediated signaling	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
cellular response to organic cyclic compound	Cytochrome P450 1A1	Homo sapiens (human)
response to hypoxia	Cytochrome P450 1A1	Homo sapiens (human)
long-chain fatty acid metabolic process	Cytochrome P450 1A1	Homo sapiens (human)
lipid hydroxylation	Cytochrome P450 1A1	Homo sapiens (human)
fatty acid metabolic process	Cytochrome P450 1A1	Homo sapiens (human)
steroid biosynthetic process	Cytochrome P450 1A1	Homo sapiens (human)
porphyrin-containing compound metabolic process	Cytochrome P450 1A1	Homo sapiens (human)
xenobiotic metabolic process	Cytochrome P450 1A1	Homo sapiens (human)
steroid metabolic process	Cytochrome P450 1A1	Homo sapiens (human)
estrogen metabolic process	Cytochrome P450 1A1	Homo sapiens (human)
amine metabolic process	Cytochrome P450 1A1	Homo sapiens (human)
response to nematode	Cytochrome P450 1A1	Homo sapiens (human)
response to herbicide	Cytochrome P450 1A1	Homo sapiens (human)
ethylene metabolic process	Cytochrome P450 1A1	Homo sapiens (human)
coumarin metabolic process	Cytochrome P450 1A1	Homo sapiens (human)
flavonoid metabolic process	Cytochrome P450 1A1	Homo sapiens (human)
response to iron(III) ion	Cytochrome P450 1A1	Homo sapiens (human)
insecticide metabolic process	Cytochrome P450 1A1	Homo sapiens (human)
dibenzo-p-dioxin catabolic process	Cytochrome P450 1A1	Homo sapiens (human)
epoxygenase P450 pathway	Cytochrome P450 1A1	Homo sapiens (human)
response to food	Cytochrome P450 1A1	Homo sapiens (human)
response to lipopolysaccharide	Cytochrome P450 1A1	Homo sapiens (human)
response to vitamin A	Cytochrome P450 1A1	Homo sapiens (human)
response to immobilization stress	Cytochrome P450 1A1	Homo sapiens (human)
vitamin D metabolic process	Cytochrome P450 1A1	Homo sapiens (human)
retinol metabolic process	Cytochrome P450 1A1	Homo sapiens (human)
long-chain fatty acid biosynthetic process	Cytochrome P450 1A1	Homo sapiens (human)
9-cis-retinoic acid biosynthetic process	Cytochrome P450 1A1	Homo sapiens (human)
camera-type eye development	Cytochrome P450 1A1	Homo sapiens (human)
nitric oxide metabolic process	Cytochrome P450 1A1	Homo sapiens (human)
response to arsenic-containing substance	Cytochrome P450 1A1	Homo sapiens (human)
digestive tract development	Cytochrome P450 1A1	Homo sapiens (human)
tissue remodeling	Cytochrome P450 1A1	Homo sapiens (human)
hydrogen peroxide biosynthetic process	Cytochrome P450 1A1	Homo sapiens (human)
response to hyperoxia	Cytochrome P450 1A1	Homo sapiens (human)
maternal process involved in parturition	Cytochrome P450 1A1	Homo sapiens (human)
hepatocyte differentiation	Cytochrome P450 1A1	Homo sapiens (human)
cellular response to copper ion	Cytochrome P450 1A1	Homo sapiens (human)
omega-hydroxylase P450 pathway	Cytochrome P450 1A1	Homo sapiens (human)
positive regulation of G1/S transition of mitotic cell cycle	Cytochrome P450 1A1	Homo sapiens (human)
response to 3-methylcholanthrene	Cytochrome P450 1A1	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)
G2/M transition of mitotic cell cycle	ATP-dependent translocase ABCB1	Homo sapiens (human)
xenobiotic metabolic process	ATP-dependent translocase ABCB1	Homo sapiens (human)
response to xenobiotic stimulus	ATP-dependent translocase ABCB1	Homo sapiens (human)
phospholipid translocation	ATP-dependent translocase ABCB1	Homo sapiens (human)
terpenoid transport	ATP-dependent translocase ABCB1	Homo sapiens (human)
regulation of response to osmotic stress	ATP-dependent translocase ABCB1	Homo sapiens (human)
transmembrane transport	ATP-dependent translocase ABCB1	Homo sapiens (human)
transepithelial transport	ATP-dependent translocase ABCB1	Homo sapiens (human)
stem cell proliferation	ATP-dependent translocase ABCB1	Homo sapiens (human)
ceramide translocation	ATP-dependent translocase ABCB1	Homo sapiens (human)
export across plasma membrane	ATP-dependent translocase ABCB1	Homo sapiens (human)
transport across blood-brain barrier	ATP-dependent translocase ABCB1	Homo sapiens (human)
positive regulation of anion channel activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
carboxylic acid transmembrane transport	ATP-dependent translocase ABCB1	Homo sapiens (human)
xenobiotic detoxification by transmembrane export across the plasma membrane	ATP-dependent translocase ABCB1	Homo sapiens (human)
xenobiotic transport across blood-brain barrier	ATP-dependent translocase ABCB1	Homo sapiens (human)
regulation of chloride transport	ATP-dependent translocase ABCB1	Homo sapiens (human)
lipid hydroxylation	Cytochrome P450 3A4	Homo sapiens (human)
lipid metabolic process	Cytochrome P450 3A4	Homo sapiens (human)
steroid catabolic process	Cytochrome P450 3A4	Homo sapiens (human)
xenobiotic metabolic process	Cytochrome P450 3A4	Homo sapiens (human)
steroid metabolic process	Cytochrome P450 3A4	Homo sapiens (human)
cholesterol metabolic process	Cytochrome P450 3A4	Homo sapiens (human)
androgen metabolic process	Cytochrome P450 3A4	Homo sapiens (human)
estrogen metabolic process	Cytochrome P450 3A4	Homo sapiens (human)
alkaloid catabolic process	Cytochrome P450 3A4	Homo sapiens (human)
monoterpenoid metabolic process	Cytochrome P450 3A4	Homo sapiens (human)
calcitriol biosynthetic process from calciol	Cytochrome P450 3A4	Homo sapiens (human)
xenobiotic catabolic process	Cytochrome P450 3A4	Homo sapiens (human)
vitamin D metabolic process	Cytochrome P450 3A4	Homo sapiens (human)
vitamin D catabolic process	Cytochrome P450 3A4	Homo sapiens (human)
retinol metabolic process	Cytochrome P450 3A4	Homo sapiens (human)
retinoic acid metabolic process	Cytochrome P450 3A4	Homo sapiens (human)
long-chain fatty acid biosynthetic process	Cytochrome P450 3A4	Homo sapiens (human)
aflatoxin metabolic process	Cytochrome P450 3A4	Homo sapiens (human)
oxidative demethylation	Cytochrome P450 3A4	Homo sapiens (human)
xenobiotic metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
steroid metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
cholesterol metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
estrogen metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
coumarin metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
alkaloid metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
alkaloid catabolic process	Cytochrome P450 2D6	Homo sapiens (human)
monoterpenoid metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
isoquinoline alkaloid metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
xenobiotic catabolic process	Cytochrome P450 2D6	Homo sapiens (human)
retinol metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
long-chain fatty acid biosynthetic process	Cytochrome P450 2D6	Homo sapiens (human)
negative regulation of binding	Cytochrome P450 2D6	Homo sapiens (human)
oxidative demethylation	Cytochrome P450 2D6	Homo sapiens (human)
negative regulation of cellular organofluorine metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
arachidonic acid metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
xenobiotic metabolic process	Cytochrome P450 2A6	Homo sapiens (human)
steroid metabolic process	Cytochrome P450 2A6	Homo sapiens (human)
coumarin metabolic process	Cytochrome P450 2A6	Homo sapiens (human)
xenobiotic catabolic process	Cytochrome P450 2A6	Homo sapiens (human)
coumarin catabolic process	Cytochrome P450 2A6	Homo sapiens (human)
epoxygenase P450 pathway	Cytochrome P450 2A6	Homo sapiens (human)
negative regulation of chronic inflammatory response	Aromatase	Homo sapiens (human)
steroid biosynthetic process	Aromatase	Homo sapiens (human)
estrogen biosynthetic process	Aromatase	Homo sapiens (human)
androgen catabolic process	Aromatase	Homo sapiens (human)
syncytium formation	Aromatase	Homo sapiens (human)
negative regulation of macrophage chemotaxis	Aromatase	Homo sapiens (human)
sterol metabolic process	Aromatase	Homo sapiens (human)
female genitalia development	Aromatase	Homo sapiens (human)
mammary gland development	Aromatase	Homo sapiens (human)
uterus development	Aromatase	Homo sapiens (human)
prostate gland growth	Aromatase	Homo sapiens (human)
testosterone biosynthetic process	Aromatase	Homo sapiens (human)
positive regulation of estradiol secretion	Aromatase	Homo sapiens (human)
female gonad development	Aromatase	Homo sapiens (human)
response to estradiol	Aromatase	Homo sapiens (human)
xenobiotic metabolic process	Cytochrome P450 2C9	Homo sapiens (human)
steroid metabolic process	Cytochrome P450 2C9	Homo sapiens (human)
cholesterol metabolic process	Cytochrome P450 2C9	Homo sapiens (human)
estrogen metabolic process	Cytochrome P450 2C9	Homo sapiens (human)
monoterpenoid metabolic process	Cytochrome P450 2C9	Homo sapiens (human)
epoxygenase P450 pathway	Cytochrome P450 2C9	Homo sapiens (human)
urea metabolic process	Cytochrome P450 2C9	Homo sapiens (human)
monocarboxylic acid metabolic process	Cytochrome P450 2C9	Homo sapiens (human)
xenobiotic catabolic process	Cytochrome P450 2C9	Homo sapiens (human)
long-chain fatty acid biosynthetic process	Cytochrome P450 2C9	Homo sapiens (human)
amide metabolic process	Cytochrome P450 2C9	Homo sapiens (human)
icosanoid biosynthetic process	Cytochrome P450 2C9	Homo sapiens (human)
oxidative demethylation	Cytochrome P450 2C9	Homo sapiens (human)
omega-hydroxylase P450 pathway	Cytochrome P450 2C9	Homo sapiens (human)
lipid metabolic process	UDP-glucuronosyltransferase 2B7	Homo sapiens (human)
xenobiotic metabolic process	UDP-glucuronosyltransferase 2B7	Homo sapiens (human)
androgen metabolic process	UDP-glucuronosyltransferase 2B7	Homo sapiens (human)
estrogen metabolic process	UDP-glucuronosyltransferase 2B7	Homo sapiens (human)
cellular glucuronidation	UDP-glucuronosyltransferase 2B7	Homo sapiens (human)
xenobiotic metabolic process	UDP-glucuronosyltransferase 1-6	Homo sapiens (human)
cellular glucuronidation	UDP-glucuronosyltransferase 1-6	Homo sapiens (human)
xenobiotic metabolic process	Cytochrome P450 2B6	Homo sapiens (human)
steroid metabolic process	Cytochrome P450 2B6	Homo sapiens (human)
xenobiotic catabolic process	Cytochrome P450 2B6	Homo sapiens (human)
cellular ketone metabolic process	Cytochrome P450 2B6	Homo sapiens (human)
epoxygenase P450 pathway	Cytochrome P450 2B6	Homo sapiens (human)
muscle contraction	Substance-K receptor	Homo sapiens (human)
tachykinin receptor signaling pathway	Substance-K receptor	Homo sapiens (human)
positive regulation of acetylcholine secretion, neurotransmission	Substance-K receptor	Homo sapiens (human)
intestine smooth muscle contraction	Substance-K receptor	Homo sapiens (human)
negative regulation of luteinizing hormone secretion	Substance-K receptor	Homo sapiens (human)
operant conditioning	Substance-K receptor	Homo sapiens (human)
positive regulation of vascular permeability	Substance-K receptor	Homo sapiens (human)
positive regulation of monoatomic ion transport	Substance-K receptor	Homo sapiens (human)
positive regulation of smooth muscle contraction	Substance-K receptor	Homo sapiens (human)
response to electrical stimulus	Substance-K receptor	Homo sapiens (human)
prolactin secretion	Substance-K receptor	Homo sapiens (human)
positive regulation of uterine smooth muscle contraction	Substance-K receptor	Homo sapiens (human)
positive regulation of flagellated sperm motility	Substance-K receptor	Homo sapiens (human)
liver development	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
bilirubin conjugation	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
xenobiotic metabolic process	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
acute-phase response	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
response to nutrient	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
steroid metabolic process	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
estrogen metabolic process	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
animal organ regeneration	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
response to lipopolysaccharide	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
retinoic acid metabolic process	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
response to starvation	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
negative regulation of steroid metabolic process	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
flavone metabolic process	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
cellular glucuronidation	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
flavonoid glucuronidation	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
xenobiotic glucuronidation	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
biphenyl catabolic process	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
cellular response to ethanol	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
cellular response to glucocorticoid stimulus	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
cellular response to estradiol stimulus	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
bilirubin conjugation	UDP-glucuronosyltransferase 1A4	Homo sapiens (human)
heme catabolic process	UDP-glucuronosyltransferase 1A4	Homo sapiens (human)
cellular glucuronidation	UDP-glucuronosyltransferase 1A4	Homo sapiens (human)
vitamin D3 metabolic process	UDP-glucuronosyltransferase 1A4	Homo sapiens (human)
prostaglandin biosynthetic process	Thromboxane-A synthase	Homo sapiens (human)
icosanoid metabolic process	Thromboxane-A synthase	Homo sapiens (human)
cyclooxygenase pathway	Thromboxane-A synthase	Homo sapiens (human)
intracellular chloride ion homeostasis	Thromboxane-A synthase	Homo sapiens (human)
response to ethanol	Thromboxane-A synthase	Homo sapiens (human)
positive regulation of vasoconstriction	Thromboxane-A synthase	Homo sapiens (human)
response to fatty acid	Thromboxane-A synthase	Homo sapiens (human)
temperature homeostasis	Adenosine receptor A1	Homo sapiens (human)
response to hypoxia	Adenosine receptor A1	Homo sapiens (human)
G protein-coupled adenosine receptor signaling pathway	Adenosine receptor A1	Homo sapiens (human)
regulation of respiratory gaseous exchange by nervous system process	Adenosine receptor A1	Homo sapiens (human)
negative regulation of acute inflammatory response	Adenosine receptor A1	Homo sapiens (human)
negative regulation of leukocyte migration	Adenosine receptor A1	Homo sapiens (human)
positive regulation of peptide secretion	Adenosine receptor A1	Homo sapiens (human)
positive regulation of systemic arterial blood pressure	Adenosine receptor A1	Homo sapiens (human)
negative regulation of systemic arterial blood pressure	Adenosine receptor A1	Homo sapiens (human)
regulation of glomerular filtration	Adenosine receptor A1	Homo sapiens (human)
protein targeting to membrane	Adenosine receptor A1	Homo sapiens (human)
phagocytosis	Adenosine receptor A1	Homo sapiens (human)
inflammatory response	Adenosine receptor A1	Homo sapiens (human)
signal transduction	Adenosine receptor A1	Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathway	Adenosine receptor A1	Homo sapiens (human)
cell-cell signaling	Adenosine receptor A1	Homo sapiens (human)
nervous system development	Adenosine receptor A1	Homo sapiens (human)
negative regulation of cell population proliferation	Adenosine receptor A1	Homo sapiens (human)
response to inorganic substance	Adenosine receptor A1	Homo sapiens (human)
negative regulation of glutamate secretion	Adenosine receptor A1	Homo sapiens (human)
response to purine-containing compound	Adenosine receptor A1	Homo sapiens (human)
lipid catabolic process	Adenosine receptor A1	Homo sapiens (human)
negative regulation of synaptic transmission, GABAergic	Adenosine receptor A1	Homo sapiens (human)
positive regulation of nucleoside transport	Adenosine receptor A1	Homo sapiens (human)
negative regulation of neurotrophin production	Adenosine receptor A1	Homo sapiens (human)
positive regulation of protein dephosphorylation	Adenosine receptor A1	Homo sapiens (human)
vasodilation	Adenosine receptor A1	Homo sapiens (human)
negative regulation of circadian sleep/wake cycle, non-REM sleep	Adenosine receptor A1	Homo sapiens (human)
negative regulation of apoptotic process	Adenosine receptor A1	Homo sapiens (human)
positive regulation of potassium ion transport	Adenosine receptor A1	Homo sapiens (human)
positive regulation of MAPK cascade	Adenosine receptor A1	Homo sapiens (human)
negative regulation of hormone secretion	Adenosine receptor A1	Homo sapiens (human)
cognition	Adenosine receptor A1	Homo sapiens (human)
leukocyte migration	Adenosine receptor A1	Homo sapiens (human)
detection of temperature stimulus involved in sensory perception of pain	Adenosine receptor A1	Homo sapiens (human)
negative regulation of lipid catabolic process	Adenosine receptor A1	Homo sapiens (human)
positive regulation of lipid catabolic process	Adenosine receptor A1	Homo sapiens (human)
regulation of sensory perception of pain	Adenosine receptor A1	Homo sapiens (human)
negative regulation of synaptic transmission, glutamatergic	Adenosine receptor A1	Homo sapiens (human)
fatty acid homeostasis	Adenosine receptor A1	Homo sapiens (human)
excitatory postsynaptic potential	Adenosine receptor A1	Homo sapiens (human)
long-term synaptic depression	Adenosine receptor A1	Homo sapiens (human)
mucus secretion	Adenosine receptor A1	Homo sapiens (human)
negative regulation of mucus secretion	Adenosine receptor A1	Homo sapiens (human)
triglyceride homeostasis	Adenosine receptor A1	Homo sapiens (human)
regulation of cardiac muscle cell contraction	Adenosine receptor A1	Homo sapiens (human)
apoptotic signaling pathway	Adenosine receptor A1	Homo sapiens (human)
regulation of presynaptic cytosolic calcium ion concentration	Adenosine receptor A1	Homo sapiens (human)
negative regulation of long-term synaptic potentiation	Adenosine receptor A1	Homo sapiens (human)
negative regulation of long-term synaptic depression	Adenosine receptor A1	Homo sapiens (human)
G protein-coupled receptor signaling pathway	Adenosine receptor A1	Homo sapiens (human)
long-chain fatty acid metabolic process	Cytochrome P450 2C19	Homo sapiens (human)
xenobiotic metabolic process	Cytochrome P450 2C19	Homo sapiens (human)
steroid metabolic process	Cytochrome P450 2C19	Homo sapiens (human)
monoterpenoid metabolic process	Cytochrome P450 2C19	Homo sapiens (human)
epoxygenase P450 pathway	Cytochrome P450 2C19	Homo sapiens (human)
xenobiotic catabolic process	Cytochrome P450 2C19	Homo sapiens (human)
omega-hydroxylase P450 pathway	Cytochrome P450 2C19	Homo sapiens (human)
leukotriene metabolic process	Multidrug resistance-associated protein 1	Homo sapiens (human)
xenobiotic metabolic process	Multidrug resistance-associated protein 1	Homo sapiens (human)
response to xenobiotic stimulus	Multidrug resistance-associated protein 1	Homo sapiens (human)
cobalamin transport	Multidrug resistance-associated protein 1	Homo sapiens (human)
sphingolipid biosynthetic process	Multidrug resistance-associated protein 1	Homo sapiens (human)
cellular response to oxidative stress	Multidrug resistance-associated protein 1	Homo sapiens (human)
heme catabolic process	Multidrug resistance-associated protein 1	Homo sapiens (human)
xenobiotic transport	Multidrug resistance-associated protein 1	Homo sapiens (human)
phospholipid translocation	Multidrug resistance-associated protein 1	Homo sapiens (human)
positive regulation of inflammatory response	Multidrug resistance-associated protein 1	Homo sapiens (human)
transmembrane transport	Multidrug resistance-associated protein 1	Homo sapiens (human)
cell chemotaxis	Multidrug resistance-associated protein 1	Homo sapiens (human)
transepithelial transport	Multidrug resistance-associated protein 1	Homo sapiens (human)
cyclic nucleotide transport	Multidrug resistance-associated protein 1	Homo sapiens (human)
leukotriene transport	Multidrug resistance-associated protein 1	Homo sapiens (human)
monoatomic anion transmembrane transport	Multidrug resistance-associated protein 1	Homo sapiens (human)
sphingolipid translocation	Multidrug resistance-associated protein 1	Homo sapiens (human)
export across plasma membrane	Multidrug resistance-associated protein 1	Homo sapiens (human)
transport across blood-brain barrier	Multidrug resistance-associated protein 1	Homo sapiens (human)
cellular response to amyloid-beta	Multidrug resistance-associated protein 1	Homo sapiens (human)
carboxylic acid transmembrane transport	Multidrug resistance-associated protein 1	Homo sapiens (human)
xenobiotic transport across blood-brain barrier	Multidrug resistance-associated protein 1	Homo sapiens (human)
glutathione transmembrane transport	Multidrug resistance-associated protein 1	Homo sapiens (human)
lipid metabolic process	UDP-glucuronosyltransferase 2B10	Homo sapiens (human)
cellular glucuronidation	UDP-glucuronosyltransferase 2B10	Homo sapiens (human)
estrogen metabolic process	UDP-glucuronosyltransferase 2B10	Homo sapiens (human)
peptidyl-serine phosphorylation	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
maturation of 5.8S rRNA	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
somitogenesis	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
negative regulation of protein phosphorylation	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
activation of innate immune response	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
B cell lineage commitment	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
immature B cell differentiation	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
pro-B cell differentiation	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
T cell lineage commitment	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
double-strand break repair	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
double-strand break repair via nonhomologous end joining	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
chromatin remodeling	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
protein phosphorylation	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
DNA damage response	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
brain development	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
heart development	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
response to gamma radiation	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
telomere capping	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
peptidyl-serine phosphorylation	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
peptidyl-threonine phosphorylation	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
mitotic G1 DNA damage checkpoint signaling	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
protein destabilization	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
cellular response to insulin stimulus	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
T cell differentiation in thymus	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
T cell receptor V(D)J recombination	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
small-subunit processome assembly	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
ectopic germ cell programmed cell death	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
protein modification process	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
regulation of circadian rhythm	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
positive regulation of apoptotic process	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
negative regulation of apoptotic process	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
innate immune response	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
positive regulation of lymphocyte differentiation	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
positive regulation of erythrocyte differentiation	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
positive regulation of translation	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
positive regulation of transcription by RNA polymerase II	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
rhythmic process	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
regulation of smooth muscle cell proliferation	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
regulation of epithelial cell proliferation	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
double-strand break repair via alternative nonhomologous end joining	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
negative regulation of cGAS/STING signaling pathway	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
regulation of hematopoietic stem cell differentiation	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
positive regulation of platelet formation	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
positive regulation of double-strand break repair via nonhomologous end joining	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
immunoglobulin V(D)J recombination	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
telomere maintenance	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
intrinsic apoptotic signaling pathway in response to DNA damage	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
xanthine catabolic process	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
cellular response to organic cyclic compound	Cytochrome P450 1B1	Homo sapiens (human)
angiogenesis	Cytochrome P450 1B1	Homo sapiens (human)
trabecular meshwork development	Cytochrome P450 1B1	Homo sapiens (human)
DNA modification	Cytochrome P450 1B1	Homo sapiens (human)
xenobiotic metabolic process	Cytochrome P450 1B1	Homo sapiens (human)
nitric oxide biosynthetic process	Cytochrome P450 1B1	Homo sapiens (human)
cell adhesion	Cytochrome P450 1B1	Homo sapiens (human)
response to nutrient	Cytochrome P450 1B1	Homo sapiens (human)
steroid metabolic process	Cytochrome P450 1B1	Homo sapiens (human)
estrogen metabolic process	Cytochrome P450 1B1	Homo sapiens (human)
negative regulation of cell population proliferation	Cytochrome P450 1B1	Homo sapiens (human)
male gonad development	Cytochrome P450 1B1	Homo sapiens (human)
intrinsic apoptotic signaling pathway in response to oxidative stress	Cytochrome P450 1B1	Homo sapiens (human)
toxin metabolic process	Cytochrome P450 1B1	Homo sapiens (human)
positive regulation of vascular endothelial growth factor production	Cytochrome P450 1B1	Homo sapiens (human)
positive regulation of smooth muscle cell migration	Cytochrome P450 1B1	Homo sapiens (human)
sterol metabolic process	Cytochrome P450 1B1	Homo sapiens (human)
arachidonic acid metabolic process	Cytochrome P450 1B1	Homo sapiens (human)
epoxygenase P450 pathway	Cytochrome P450 1B1	Homo sapiens (human)
collagen fibril organization	Cytochrome P450 1B1	Homo sapiens (human)
adrenal gland development	Cytochrome P450 1B1	Homo sapiens (human)
negative regulation of cell migration	Cytochrome P450 1B1	Homo sapiens (human)
negative regulation of NF-kappaB transcription factor activity	Cytochrome P450 1B1	Homo sapiens (human)
response to follicle-stimulating hormone	Cytochrome P450 1B1	Homo sapiens (human)
response to estradiol	Cytochrome P450 1B1	Homo sapiens (human)
negative regulation of cell adhesion mediated by integrin	Cytochrome P450 1B1	Homo sapiens (human)
benzene-containing compound metabolic process	Cytochrome P450 1B1	Homo sapiens (human)
retinol metabolic process	Cytochrome P450 1B1	Homo sapiens (human)
retinal metabolic process	Cytochrome P450 1B1	Homo sapiens (human)
positive regulation of apoptotic process	Cytochrome P450 1B1	Homo sapiens (human)
blood vessel endothelial cell migration	Cytochrome P450 1B1	Homo sapiens (human)
endothelial cell migration	Cytochrome P450 1B1	Homo sapiens (human)
estrous cycle	Cytochrome P450 1B1	Homo sapiens (human)
positive regulation of translation	Cytochrome P450 1B1	Homo sapiens (human)
positive regulation of angiogenesis	Cytochrome P450 1B1	Homo sapiens (human)
positive regulation of receptor signaling pathway via JAK-STAT	Cytochrome P450 1B1	Homo sapiens (human)
membrane lipid catabolic process	Cytochrome P450 1B1	Homo sapiens (human)
response to arsenic-containing substance	Cytochrome P450 1B1	Homo sapiens (human)
blood vessel morphogenesis	Cytochrome P450 1B1	Homo sapiens (human)
retinal blood vessel morphogenesis	Cytochrome P450 1B1	Homo sapiens (human)
ganglion development	Cytochrome P450 1B1	Homo sapiens (human)
cellular response to hydrogen peroxide	Cytochrome P450 1B1	Homo sapiens (human)
cellular response to cAMP	Cytochrome P450 1B1	Homo sapiens (human)
cellular response to tumor necrosis factor	Cytochrome P450 1B1	Homo sapiens (human)
cellular response to luteinizing hormone stimulus	Cytochrome P450 1B1	Homo sapiens (human)
cellular response to cortisol stimulus	Cytochrome P450 1B1	Homo sapiens (human)
cellular response to progesterone stimulus	Cytochrome P450 1B1	Homo sapiens (human)
response to dexamethasone	Cytochrome P450 1B1	Homo sapiens (human)
endothelial cell-cell adhesion	Cytochrome P450 1B1	Homo sapiens (human)
response to indole-3-methanol	Cytochrome P450 1B1	Homo sapiens (human)
cellular response to toxic substance	Cytochrome P450 1B1	Homo sapiens (human)
omega-hydroxylase P450 pathway	Cytochrome P450 1B1	Homo sapiens (human)
response to 3-methylcholanthrene	Cytochrome P450 1B1	Homo sapiens (human)
regulation of reactive oxygen species metabolic process	Cytochrome P450 1B1	Homo sapiens (human)
positive regulation of reactive oxygen species metabolic process	Cytochrome P450 1B1	Homo sapiens (human)
positive regulation of DNA biosynthetic process	Cytochrome P450 1B1	Homo sapiens (human)
lipid transport	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
organic anion transport	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
urate transport	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
biotin transport	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
sphingolipid biosynthetic process	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
riboflavin transport	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
urate metabolic process	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
transmembrane transport	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
transepithelial transport	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
renal urate salt excretion	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
export across plasma membrane	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
transport across blood-brain barrier	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
cellular detoxification	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
xenobiotic transport across blood-brain barrier	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
3',5'-cyclic-nucleotide phosphodiesterase activity	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
protein binding	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
cGMP binding	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
metal ion binding	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
3',5'-cyclic-GMP phosphodiesterase activity	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
3',5'-cyclic-AMP phosphodiesterase activity	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
monooxygenase activity	Cytochrome P450 1A1	Homo sapiens (human)
iron ion binding	Cytochrome P450 1A1	Homo sapiens (human)
protein binding	Cytochrome P450 1A1	Homo sapiens (human)
arachidonic acid monooxygenase activity	Cytochrome P450 1A1	Homo sapiens (human)
oxidoreductase activity	Cytochrome P450 1A1	Homo sapiens (human)
oxidoreductase activity, acting on diphenols and related substances as donors	Cytochrome P450 1A1	Homo sapiens (human)
flavonoid 3'-monooxygenase activity	Cytochrome P450 1A1	Homo sapiens (human)
oxygen binding	Cytochrome P450 1A1	Homo sapiens (human)
enzyme binding	Cytochrome P450 1A1	Homo sapiens (human)
heme binding	Cytochrome P450 1A1	Homo sapiens (human)
Hsp70 protein binding	Cytochrome P450 1A1	Homo sapiens (human)
demethylase activity	Cytochrome P450 1A1	Homo sapiens (human)
Hsp90 protein binding	Cytochrome P450 1A1	Homo sapiens (human)
aromatase activity	Cytochrome P450 1A1	Homo sapiens (human)
vitamin D 24-hydroxylase activity	Cytochrome P450 1A1	Homo sapiens (human)
estrogen 16-alpha-hydroxylase activity	Cytochrome P450 1A1	Homo sapiens (human)
estrogen 2-hydroxylase activity	Cytochrome P450 1A1	Homo sapiens (human)
long-chain fatty acid omega-hydroxylase activity	Cytochrome P450 1A1	Homo sapiens (human)
hydroperoxy icosatetraenoate dehydratase activity	Cytochrome P450 1A1	Homo sapiens (human)
long-chain fatty acid omega-1 hydroxylase activity	Cytochrome P450 1A1	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 binding	ATP-dependent translocase ABCB1	Homo sapiens (human)
ATP binding	ATP-dependent translocase ABCB1	Homo sapiens (human)
ABC-type xenobiotic transporter activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
efflux transmembrane transporter activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
ATP hydrolysis activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
transmembrane transporter activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
ubiquitin protein ligase binding	ATP-dependent translocase ABCB1	Homo sapiens (human)
ATPase-coupled transmembrane transporter activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
xenobiotic transmembrane transporter activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
carboxylic acid transmembrane transporter activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
phosphatidylcholine floppase activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
phosphatidylethanolamine flippase activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
ceramide floppase activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
floppase activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
monooxygenase activity	Cytochrome P450 3A4	Homo sapiens (human)
steroid binding	Cytochrome P450 3A4	Homo sapiens (human)
iron ion binding	Cytochrome P450 3A4	Homo sapiens (human)
protein binding	Cytochrome P450 3A4	Homo sapiens (human)
steroid hydroxylase activity	Cytochrome P450 3A4	Homo sapiens (human)
retinoic acid 4-hydroxylase activity	Cytochrome P450 3A4	Homo sapiens (human)
oxidoreductase activity	Cytochrome P450 3A4	Homo sapiens (human)
oxygen binding	Cytochrome P450 3A4	Homo sapiens (human)
enzyme binding	Cytochrome P450 3A4	Homo sapiens (human)
heme binding	Cytochrome P450 3A4	Homo sapiens (human)
vitamin D3 25-hydroxylase activity	Cytochrome P450 3A4	Homo sapiens (human)
caffeine oxidase activity	Cytochrome P450 3A4	Homo sapiens (human)
quinine 3-monooxygenase activity	Cytochrome P450 3A4	Homo sapiens (human)
testosterone 6-beta-hydroxylase activity	Cytochrome P450 3A4	Homo sapiens (human)
1-alpha,25-dihydroxyvitamin D3 23-hydroxylase activity	Cytochrome P450 3A4	Homo sapiens (human)
anandamide 8,9 epoxidase activity	Cytochrome P450 3A4	Homo sapiens (human)
anandamide 11,12 epoxidase activity	Cytochrome P450 3A4	Homo sapiens (human)
anandamide 14,15 epoxidase activity	Cytochrome P450 3A4	Homo sapiens (human)
aromatase activity	Cytochrome P450 3A4	Homo sapiens (human)
vitamin D 24-hydroxylase activity	Cytochrome P450 3A4	Homo sapiens (human)
estrogen 16-alpha-hydroxylase activity	Cytochrome P450 3A4	Homo sapiens (human)
estrogen 2-hydroxylase activity	Cytochrome P450 3A4	Homo sapiens (human)
1,8-cineole 2-exo-monooxygenase activity	Cytochrome P450 3A4	Homo sapiens (human)
monooxygenase activity	Cytochrome P450 2D6	Homo sapiens (human)
iron ion binding	Cytochrome P450 2D6	Homo sapiens (human)
oxidoreductase activity	Cytochrome P450 2D6	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 2D6	Homo sapiens (human)
heme binding	Cytochrome P450 2D6	Homo sapiens (human)
anandamide 8,9 epoxidase activity	Cytochrome P450 2D6	Homo sapiens (human)
anandamide 11,12 epoxidase activity	Cytochrome P450 2D6	Homo sapiens (human)
anandamide 14,15 epoxidase activity	Cytochrome P450 2D6	Homo sapiens (human)
iron ion binding	Cytochrome P450 2A6	Homo sapiens (human)
coumarin 7-hydroxylase activity	Cytochrome P450 2A6	Homo sapiens (human)
enzyme binding	Cytochrome P450 2A6	Homo sapiens (human)
heme binding	Cytochrome P450 2A6	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 2A6	Homo sapiens (human)
arachidonic acid epoxygenase activity	Cytochrome P450 2A6	Homo sapiens (human)
iron ion binding	Aromatase	Homo sapiens (human)
steroid hydroxylase activity	Aromatase	Homo sapiens (human)
electron transfer activity	Aromatase	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	Aromatase	Homo sapiens (human)
oxygen binding	Aromatase	Homo sapiens (human)
heme binding	Aromatase	Homo sapiens (human)
aromatase activity	Aromatase	Homo sapiens (human)
monooxygenase activity	Cytochrome P450 2C9	Homo sapiens (human)
iron ion binding	Cytochrome P450 2C9	Homo sapiens (human)
arachidonic acid epoxygenase activity	Cytochrome P450 2C9	Homo sapiens (human)
steroid hydroxylase activity	Cytochrome P450 2C9	Homo sapiens (human)
arachidonic acid 14,15-epoxygenase activity	Cytochrome P450 2C9	Homo sapiens (human)
arachidonic acid 11,12-epoxygenase activity	Cytochrome P450 2C9	Homo sapiens (human)
oxidoreductase activity	Cytochrome P450 2C9	Homo sapiens (human)
(S)-limonene 6-monooxygenase activity	Cytochrome P450 2C9	Homo sapiens (human)
(S)-limonene 7-monooxygenase activity	Cytochrome P450 2C9	Homo sapiens (human)
caffeine oxidase activity	Cytochrome P450 2C9	Homo sapiens (human)
(R)-limonene 6-monooxygenase activity	Cytochrome P450 2C9	Homo sapiens (human)
aromatase activity	Cytochrome P450 2C9	Homo sapiens (human)
heme binding	Cytochrome P450 2C9	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 2C9	Homo sapiens (human)
retinoic acid binding	UDP-glucuronosyltransferase 2B7	Homo sapiens (human)
glucuronosyltransferase activity	UDP-glucuronosyltransferase 2B7	Homo sapiens (human)
retinoic acid binding	UDP-glucuronosyltransferase 1-6	Homo sapiens (human)
glucuronosyltransferase activity	UDP-glucuronosyltransferase 1-6	Homo sapiens (human)
enzyme binding	UDP-glucuronosyltransferase 1-6	Homo sapiens (human)
protein homodimerization activity	UDP-glucuronosyltransferase 1-6	Homo sapiens (human)
protein heterodimerization activity	UDP-glucuronosyltransferase 1-6	Homo sapiens (human)
monooxygenase activity	Cytochrome P450 2B6	Homo sapiens (human)
iron ion binding	Cytochrome P450 2B6	Homo sapiens (human)
testosterone 16-alpha-hydroxylase activity	Cytochrome P450 2B6	Homo sapiens (human)
heme binding	Cytochrome P450 2B6	Homo sapiens (human)
testosterone 16-beta-hydroxylase activity	Cytochrome P450 2B6	Homo sapiens (human)
anandamide 8,9 epoxidase activity	Cytochrome P450 2B6	Homo sapiens (human)
anandamide 11,12 epoxidase activity	Cytochrome P450 2B6	Homo sapiens (human)
anandamide 14,15 epoxidase activity	Cytochrome P450 2B6	Homo sapiens (human)
estrogen 2-hydroxylase activity	Cytochrome P450 2B6	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 2B6	Homo sapiens (human)
arachidonic acid epoxygenase activity	Cytochrome P450 2B6	Homo sapiens (human)
tachykinin receptor activity	Substance-K receptor	Homo sapiens (human)
protein binding	Substance-K receptor	Homo sapiens (human)
substance K receptor activity	Substance-K receptor	Homo sapiens (human)
retinoic acid binding	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
enzyme inhibitor activity	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
steroid binding	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
glucuronosyltransferase activity	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
enzyme binding	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
protein homodimerization activity	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
protein heterodimerization activity	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
retinoic acid binding	UDP-glucuronosyltransferase 1A4	Homo sapiens (human)
glucuronosyltransferase activity	UDP-glucuronosyltransferase 1A4	Homo sapiens (human)
enzyme binding	UDP-glucuronosyltransferase 1A4	Homo sapiens (human)
protein homodimerization activity	UDP-glucuronosyltransferase 1A4	Homo sapiens (human)
protein heterodimerization activity	UDP-glucuronosyltransferase 1A4	Homo sapiens (human)
monooxygenase activity	Thromboxane-A synthase	Homo sapiens (human)
thromboxane-A synthase activity	Thromboxane-A synthase	Homo sapiens (human)
iron ion binding	Thromboxane-A synthase	Homo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen	Thromboxane-A synthase	Homo sapiens (human)
heme binding	Thromboxane-A synthase	Homo sapiens (human)
12-hydroxyheptadecatrienoic acid synthase activity	Thromboxane-A synthase	Homo sapiens (human)
hydroperoxy icosatetraenoate dehydratase activity	Thromboxane-A synthase	Homo sapiens (human)
G protein-coupled receptor binding	Adenosine receptor A1	Homo sapiens (human)
purine nucleoside binding	Adenosine receptor A1	Homo sapiens (human)
protein binding	Adenosine receptor A1	Homo sapiens (human)
heat shock protein binding	Adenosine receptor A1	Homo sapiens (human)
G-protein beta/gamma-subunit complex binding	Adenosine receptor A1	Homo sapiens (human)
heterotrimeric G-protein binding	Adenosine receptor A1	Homo sapiens (human)
protein heterodimerization activity	Adenosine receptor A1	Homo sapiens (human)
G protein-coupled adenosine receptor activity	Adenosine receptor A1	Homo sapiens (human)
monooxygenase activity	Cytochrome P450 2C19	Homo sapiens (human)
iron ion binding	Cytochrome P450 2C19	Homo sapiens (human)
steroid hydroxylase activity	Cytochrome P450 2C19	Homo sapiens (human)
oxidoreductase activity	Cytochrome P450 2C19	Homo sapiens (human)
(S)-limonene 6-monooxygenase activity	Cytochrome P450 2C19	Homo sapiens (human)
(S)-limonene 7-monooxygenase activity	Cytochrome P450 2C19	Homo sapiens (human)
oxygen binding	Cytochrome P450 2C19	Homo sapiens (human)
enzyme binding	Cytochrome P450 2C19	Homo sapiens (human)
heme binding	Cytochrome P450 2C19	Homo sapiens (human)
(R)-limonene 6-monooxygenase activity	Cytochrome P450 2C19	Homo sapiens (human)
aromatase activity	Cytochrome P450 2C19	Homo sapiens (human)
long-chain fatty acid omega-1 hydroxylase activity	Cytochrome P450 2C19	Homo sapiens (human)
arachidonic acid epoxygenase activity	Cytochrome P450 2C19	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 2C19	Homo sapiens (human)
ATP binding	Multidrug resistance-associated protein 1	Homo sapiens (human)
ABC-type vitamin B12 transporter activity	Multidrug resistance-associated protein 1	Homo sapiens (human)
ABC-type glutathione S-conjugate transporter activity	Multidrug resistance-associated protein 1	Homo sapiens (human)
efflux transmembrane transporter activity	Multidrug resistance-associated protein 1	Homo sapiens (human)
ATP hydrolysis activity	Multidrug resistance-associated protein 1	Homo sapiens (human)
ATPase-coupled lipid transmembrane transporter activity	Multidrug resistance-associated protein 1	Homo sapiens (human)
glutathione transmembrane transporter activity	Multidrug resistance-associated protein 1	Homo sapiens (human)
ATPase-coupled transmembrane transporter activity	Multidrug resistance-associated protein 1	Homo sapiens (human)
xenobiotic transmembrane transporter activity	Multidrug resistance-associated protein 1	Homo sapiens (human)
ATPase-coupled inorganic anion transmembrane transporter activity	Multidrug resistance-associated protein 1	Homo sapiens (human)
sphingolipid transporter activity	Multidrug resistance-associated protein 1	Homo sapiens (human)
carboxylic acid transmembrane transporter activity	Multidrug resistance-associated protein 1	Homo sapiens (human)
ABC-type transporter activity	Multidrug resistance-associated protein 1	Homo sapiens (human)
ABC-type xenobiotic transporter activity	Multidrug resistance-associated protein 1	Homo sapiens (human)
glucuronosyltransferase activity	UDP-glucuronosyltransferase 2B10	Homo sapiens (human)
UDP-glycosyltransferase activity	UDP-glucuronosyltransferase 2B10	Homo sapiens (human)
double-stranded DNA binding	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
RNA binding	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
protein kinase activity	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
protein serine/threonine kinase activity	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
DNA-dependent protein kinase activity	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
protein binding	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
ATP binding	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
enzyme binding	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
protein domain specific binding	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
U3 snoRNA binding	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
histone H2AXS139 kinase activity	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor binding	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
protein serine kinase activity	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
xanthine dehydrogenase activity	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
xanthine oxidase activity	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
iron ion binding	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
molybdenum ion binding	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
protein homodimerization activity	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
molybdopterin cofactor binding	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
flavin adenine dinucleotide binding	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
2 iron, 2 sulfur cluster binding	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
FAD binding	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
monooxygenase activity	Cytochrome P450 1B1	Homo sapiens (human)
iron ion binding	Cytochrome P450 1B1	Homo sapiens (human)
protein binding	Cytochrome P450 1B1	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 1B1	Homo sapiens (human)
heme binding	Cytochrome P450 1B1	Homo sapiens (human)
aromatase activity	Cytochrome P450 1B1	Homo sapiens (human)
estrogen 16-alpha-hydroxylase activity	Cytochrome P450 1B1	Homo sapiens (human)
hydroperoxy icosatetraenoate dehydratase activity	Cytochrome P450 1B1	Homo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, NAD(P)H as one donor, and incorporation of one atom of oxygen	Cytochrome P450 1B1	Homo sapiens (human)
protein binding	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
ATP binding	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
organic anion transmembrane transporter activity	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
ABC-type xenobiotic transporter activity	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
urate transmembrane transporter activity	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
biotin transmembrane transporter activity	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
efflux transmembrane transporter activity	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
ATP hydrolysis activity	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
riboflavin transmembrane transporter activity	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
ATPase-coupled transmembrane transporter activity	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
identical protein binding	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
protein homodimerization activity	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
xenobiotic transmembrane transporter activity	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
sphingolipid transporter activity	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
cellular_component	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
cytosol	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
mitochondrial inner membrane	Cytochrome P450 1A1	Homo sapiens (human)
endoplasmic reticulum membrane	Cytochrome P450 1A1	Homo sapiens (human)
intracellular membrane-bounded organelle	Cytochrome P450 1A1	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)
cytoplasm	ATP-dependent translocase ABCB1	Homo sapiens (human)
plasma membrane	ATP-dependent translocase ABCB1	Homo sapiens (human)
cell surface	ATP-dependent translocase ABCB1	Homo sapiens (human)
membrane	ATP-dependent translocase ABCB1	Homo sapiens (human)
apical plasma membrane	ATP-dependent translocase ABCB1	Homo sapiens (human)
extracellular exosome	ATP-dependent translocase ABCB1	Homo sapiens (human)
external side of apical plasma membrane	ATP-dependent translocase ABCB1	Homo sapiens (human)
plasma membrane	ATP-dependent translocase ABCB1	Homo sapiens (human)
cytoplasm	Cytochrome P450 3A4	Homo sapiens (human)
endoplasmic reticulum membrane	Cytochrome P450 3A4	Homo sapiens (human)
intracellular membrane-bounded organelle	Cytochrome P450 3A4	Homo sapiens (human)
mitochondrion	Cytochrome P450 2D6	Homo sapiens (human)
endoplasmic reticulum	Cytochrome P450 2D6	Homo sapiens (human)
endoplasmic reticulum membrane	Cytochrome P450 2D6	Homo sapiens (human)
cytoplasm	Cytochrome P450 2D6	Homo sapiens (human)
intracellular membrane-bounded organelle	Cytochrome P450 2D6	Homo sapiens (human)
endoplasmic reticulum membrane	Cytochrome P450 2A6	Homo sapiens (human)
cytoplasmic microtubule	Cytochrome P450 2A6	Homo sapiens (human)
intracellular membrane-bounded organelle	Cytochrome P450 2A6	Homo sapiens (human)
cytoplasm	Cytochrome P450 2A6	Homo sapiens (human)
endoplasmic reticulum	Aromatase	Homo sapiens (human)
endoplasmic reticulum membrane	Aromatase	Homo sapiens (human)
membrane	Aromatase	Homo sapiens (human)
endoplasmic reticulum	Aromatase	Homo sapiens (human)
endoplasmic reticulum membrane	Cytochrome P450 2C9	Homo sapiens (human)
plasma membrane	Cytochrome P450 2C9	Homo sapiens (human)
intracellular membrane-bounded organelle	Cytochrome P450 2C9	Homo sapiens (human)
cytoplasm	Cytochrome P450 2C9	Homo sapiens (human)
intracellular membrane-bounded organelle	Cytochrome P450 2C9	Homo sapiens (human)
endoplasmic reticulum membrane	UDP-glucuronosyltransferase 2B7	Homo sapiens (human)
membrane	UDP-glucuronosyltransferase 2B7	Homo sapiens (human)
plasma membrane	Gamma-aminobutyric acid receptor subunit gamma-2	Rattus norvegicus (Norway rat)
endoplasmic reticulum	UDP-glucuronosyltransferase 1-6	Homo sapiens (human)
endoplasmic reticulum membrane	UDP-glucuronosyltransferase 1-6	Homo sapiens (human)
intracellular membrane-bounded organelle	UDP-glucuronosyltransferase 1-6	Homo sapiens (human)
endoplasmic reticulum	UDP-glucuronosyltransferase 1-6	Homo sapiens (human)
endoplasmic reticulum membrane	Cytochrome P450 2B6	Homo sapiens (human)
intracellular membrane-bounded organelle	Cytochrome P450 2B6	Homo sapiens (human)
cytoplasm	Cytochrome P450 2B6	Homo sapiens (human)
plasma membrane	Substance-K receptor	Homo sapiens (human)
sperm flagellum	Substance-K receptor	Homo sapiens (human)
sperm head	Substance-K receptor	Homo sapiens (human)
sperm midpiece	Substance-K receptor	Homo sapiens (human)
sperm midpiece	Substance-K receptor	Homo sapiens (human)
plasma membrane	Substance-K receptor	Homo sapiens (human)
endoplasmic reticulum	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
endoplasmic reticulum membrane	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
plasma membrane	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
perinuclear region of cytoplasm	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
endoplasmic reticulum chaperone complex	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
cytochrome complex	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
endoplasmic reticulum	UDP-glucuronosyltransferase 1A1	Homo sapiens (human)
endoplasmic reticulum	UDP-glucuronosyltransferase 1A4	Homo sapiens (human)
endoplasmic reticulum membrane	UDP-glucuronosyltransferase 1A4	Homo sapiens (human)
endoplasmic reticulum	UDP-glucuronosyltransferase 1A4	Homo sapiens (human)
endoplasmic reticulum	Thromboxane-A synthase	Homo sapiens (human)
endoplasmic reticulum membrane	Thromboxane-A synthase	Homo sapiens (human)
cytosol	Thromboxane-A synthase	Homo sapiens (human)
plasma membrane	Adenosine receptor A1	Homo sapiens (human)
plasma membrane	Adenosine receptor A1	Homo sapiens (human)
basolateral plasma membrane	Adenosine receptor A1	Homo sapiens (human)
axolemma	Adenosine receptor A1	Homo sapiens (human)
asymmetric synapse	Adenosine receptor A1	Homo sapiens (human)
presynaptic membrane	Adenosine receptor A1	Homo sapiens (human)
neuronal cell body	Adenosine receptor A1	Homo sapiens (human)
terminal bouton	Adenosine receptor A1	Homo sapiens (human)
dendritic spine	Adenosine receptor A1	Homo sapiens (human)
calyx of Held	Adenosine receptor A1	Homo sapiens (human)
postsynaptic membrane	Adenosine receptor A1	Homo sapiens (human)
presynaptic active zone	Adenosine receptor A1	Homo sapiens (human)
synapse	Adenosine receptor A1	Homo sapiens (human)
dendrite	Adenosine receptor A1	Homo sapiens (human)
endoplasmic reticulum membrane	Cytochrome P450 2C19	Homo sapiens (human)
plasma membrane	Cytochrome P450 2C19	Homo sapiens (human)
intracellular membrane-bounded organelle	Cytochrome P450 2C19	Homo sapiens (human)
intracellular membrane-bounded organelle	Cytochrome P450 2C19	Homo sapiens (human)
cytoplasm	Cytochrome P450 2C19	Homo sapiens (human)
plasma membrane	Multidrug resistance-associated protein 1	Homo sapiens (human)
basal plasma membrane	Multidrug resistance-associated protein 1	Homo sapiens (human)
membrane	Multidrug resistance-associated protein 1	Homo sapiens (human)
basolateral plasma membrane	Multidrug resistance-associated protein 1	Homo sapiens (human)
apical plasma membrane	Multidrug resistance-associated protein 1	Homo sapiens (human)
lateral plasma membrane	Multidrug resistance-associated protein 1	Homo sapiens (human)
extracellular exosome	Multidrug resistance-associated protein 1	Homo sapiens (human)
basolateral plasma membrane	Multidrug resistance-associated protein 1	Homo sapiens (human)
endoplasmic reticulum membrane	UDP-glucuronosyltransferase 2B10	Homo sapiens (human)
plasma membrane	Gamma-aminobutyric acid receptor subunit alpha-1	Rattus norvegicus (Norway rat)
plasma membrane	Gamma-aminobutyric acid receptor subunit beta-2	Rattus norvegicus (Norway rat)
chromosome, telomeric region	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
nucleus	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
nucleoplasm	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
nucleolus	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
cytosol	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
membrane	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
DNA-dependent protein kinase complex	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
chromatin	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
transcription regulator complex	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
DNA-dependent protein kinase-DNA ligase 4 complex	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
small-subunit processome	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
protein-containing complex	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
protein-DNA complex	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
nonhomologous end joining complex	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
nucleus	DNA-dependent protein kinase catalytic subunit	Homo sapiens (human)
extracellular space	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
peroxisome	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
xanthine dehydrogenase complex	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
mitochondrion	Cytochrome P450 1B1	Homo sapiens (human)
endoplasmic reticulum membrane	Cytochrome P450 1B1	Homo sapiens (human)
intracellular membrane-bounded organelle	Cytochrome P450 1B1	Homo sapiens (human)
nucleoplasm	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
plasma membrane	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
apical plasma membrane	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
brush border membrane	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
mitochondrial membrane	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
membrane raft	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
external side of apical plasma membrane	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
plasma membrane	Broad substrate specificity ATP-binding cassette transporter ABCG2	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (273)

Assay ID	Title	Year	Journal	Article
AID1802994	UDP-glucuronosyltransferase Activity Assay from Article 10.3109/14756366.2010.518965: \\The inhibition study of human UDP-glucuronosyltransferases with cytochrome P450 selective substrates and inhibitors.\\	2011	Journal of enzyme inhibition and medicinal chemistry, Jun, Volume: 26, Issue:3	The inhibition study of human UDP-glucuronosyltransferases with cytochrome P450 selective substrates and inhibitors.
AID1387230	Inhibition of recombinant human CYP1B1 incubated for 45 mins using 7-ethyl-O-resorufin substrate in presence of NADPH regenerating system by fluorescence based ethoxyresorufin-O-deethylase assay	2018	Journal of medicinal chemistry, 10-25, Volume: 61, Issue:20	Targeting Cytochrome P450 (CYP) 1B1 Enzyme with Four Series of A-Ring Substituted Estrane Derivatives: Design, Synthesis, Inhibitory Activity, and Selectivity.
AID1164253	Inhibition of human recombinant CYP1A2 incubated for 5 mins by fluorescence assay	2014	ACS medicinal chemistry letters, Sep-11, Volume: 5, Issue:9	Exploration of 3-Aminoazetidines as Triple Reuptake Inhibitors by Bioisosteric Modification of 3-α-Oxyazetidine.
AID1816695	Inhibition of CYP1A2 (unknown origin) at 0.2 uM using phenacetin as substrate relative to control	2021	European journal of medicinal chemistry, Aug-05, Volume: 220	Design, synthesis, and biological evaluation of novel dual inhibitors targeting lysine specific demethylase 1 (LSD1) and histone deacetylases (HDAC) for treatment of gastric cancer.
AID1504637	Inhibition of recombinant human CYP1B1 expressed in supersomes coexpressing P450 reductase at 0.3 uM using 7-ethyl-O-resorufin as substrate after 45 mins in presence of NADPH by fluorescence assay relative to control	2017	ACS medicinal chemistry letters, Nov-09, Volume: 8, Issue:11	Structure-Based Design and Synthesis of New Estrane-Pyridine Derivatives as Cytochrome P450 (CYP) 1B1 Inhibitors.
AID1165279	Inhibition of human CYP1A2 at 10 uM	2014	Journal of medicinal chemistry, Oct-23, Volume: 57, Issue:20	Development of (E)-2-((1,4-dimethylpiperazin-2-ylidene)amino)-5-nitro-N-phenylbenzamide, ML336: Novel 2-amidinophenylbenzamides as potent inhibitors of venezuelan equine encephalitis virus.
AID1368058	Inhibition of recombinant human CYP1A1 expressed in HEK293 cells using 7-ethoxyresorufin as substrate pretreated for 30 mins followed by substrate addition measured for 60 mins by fluorescence assay	2017	Bioorganic & medicinal chemistry letters, 12-15, Volume: 27, Issue:24	(E)-3-(3,4,5-Trimethoxyphenyl)-1-(pyridin-4-yl)prop-2-en-1-one, a heterocyclic chalcone is a potent and selective CYP1A1 inhibitor and cancer chemopreventive agent.
AID1533288	Selectivity ratio of IC50 for recombinant human CYP1A2 expressed in Escherichia coli membranes to IC50 for recombinant human CYP1B1 expressed in Escherichia coli membranes	2018	ACS medicinal chemistry letters, Dec-13, Volume: 9, Issue:12	Adaptable Small Ligand of CYP1 Enzymes for Use in Understanding the Structural Features Determining Isoform Selectivity.
AID1387232	Selectivity index, ratio of IC50 for inhibition of recombinant human CYP1A1 to IC50 for inhibition of recombinant human CYP1B1	2018	Journal of medicinal chemistry, 10-25, Volume: 61, Issue:20	Targeting Cytochrome P450 (CYP) 1B1 Enzyme with Four Series of A-Ring Substituted Estrane Derivatives: Design, Synthesis, Inhibitory Activity, and Selectivity.
AID1446940	Inhibition of recombinant human CYP1A1 expressed in Escherichia coli DH5[alpha] using 7-ethoxyresorufin/3-cyano-7-ethoxycoumarin as substrate in presence of NADPH by EROD assay	2017	European journal of medicinal chemistry, Apr-21, Volume: 130	Quinazoline derivatives as selective CYP1B1 inhibitors.
AID1450067	Inhibition of recombinant human CYP1A2 expressed in insect cells using EOMCC as substrate pretreated for 10 mins followed by substrate addition measured every minute for 15 mins in presence of NADP+ by fluorescence assay	2017	Bioorganic & medicinal chemistry letters, 06-01, Volume: 27, Issue:11	Cytochrome P450 binding studies of novel tacrine derivatives: Predicting the risk of hepatotoxicity.
AID1515297	Selectivity ratio of IC50 for human recombinant CYP1A1 to IC50 for human recombinant CYP1B1	2019	Bioorganic & medicinal chemistry, 01-15, Volume: 27, Issue:2	Design and synthesis of selective CYP1B1 inhibitor via dearomatization of α-naphthoflavone.
AID1446925	Inhibition of human CYP1A2 expressed in yeast microsomal membranes using 7-ethoxyresorufin/3-cyano-7-ethoxycoumarin/7-ethoxy-methyloxy-3-cyanocoumarin as substrate by fluorescence assay	2017	European journal of medicinal chemistry, Apr-21, Volume: 130	Quinazoline derivatives as selective CYP1B1 inhibitors.
AID1368054	Inhibition of human CYP2C19 expressed in yeast microsomal membranes using 3-cyano-7-ethoxycoumarin as substrate measured after 10 mins by fluorescence assay	2017	Bioorganic & medicinal chemistry letters, 12-15, Volume: 27, Issue:24	(E)-3-(3,4,5-Trimethoxyphenyl)-1-(pyridin-4-yl)prop-2-en-1-one, a heterocyclic chalcone is a potent and selective CYP1A1 inhibitor and cancer chemopreventive agent.
AID1239149	Inhibition of human microsomal CYP1A2-dependent methoxyresorufin-O-demethylase activity by spectrofluorimetric analysis in presence of NADPH regenerating solution	2015	Journal of medicinal chemistry, Aug-27, Volume: 58, Issue:16	A Ligand-Based Drug Design. Discovery of 4-Trifluoromethyl-7,8-pyranocoumarin as a Selective Inhibitor of Human Cytochrome P450 1A2.
AID1239152	Selectivity ratio of Ki for human microsomal CYP1B1 to Ki for human microsomal CYP1A2	2015	Journal of medicinal chemistry, Aug-27, Volume: 58, Issue:16	A Ligand-Based Drug Design. Discovery of 4-Trifluoromethyl-7,8-pyranocoumarin as a Selective Inhibitor of Human Cytochrome P450 1A2.
AID1488361	Inhibition of human CYP2C19 bound to yeast microsomal membrane using 3-cyano-7-ethoxycoumarin as substrate after 10 mins by fluorescence assay	2017	Bioorganic & medicinal chemistry letters, 08-15, Volume: 27, Issue:16	Synthesis and biological evaluation of pyrrole-based chalcones as CYP1 enzyme inhibitors, for possible prevention of cancer and overcoming cisplatin resistance.
AID1334859	Inhibition of CYP1A2 in human liver microsomes using phenacetin as substrate preincubated for 10 mins followed by NADPH addition measured after 10 mins by LC/MS/MS method	2017	Bioorganic & medicinal chemistry, 01-15, Volume: 25, Issue:2	Discovery of biphenyl imidazole derivatives as potent antifungal agents: Design, synthesis, and structure-activity relationship studies.
AID1441877	Inhibition of human liver CYP1A1 expressed in Saccharomyces cerevisiae YY7 microsomal membranes using 7-ethoxyresorufin as substrate after 10 mins by fluorescence assay	2017	European journal of medicinal chemistry, Mar-31, Volume: 129	Discovery and characterization of novel CYP1B1 inhibitors based on heterocyclic chalcones: Overcoming cisplatin resistance in CYP1B1-overexpressing lines.
AID1407672	Inhibition of recombinant human CYP1A2 expressed in insect cell microsomes at 1 uM using Luciferin-ME as substrate preincubated for 10 mins followed by NADPH addition measured after 30 mins by luminometric method	2018	European journal of medicinal chemistry, Sep-05, Volume: 157	Hedgehog pathway inhibitors of the acylthiourea and acylguanidine class show antitumor activity on colon cancer in vitro and in vivo.
AID1411737	Inhibition of recombinant human CYP2C19 expressed in baker's yeast-derived microsomes (Sacchrosomes) at 10 uM using 3-cyano-7-ethoxycoumarin substrate by EROD assay relative to control	2018	MedChemComm, Feb-01, Volume: 9, Issue:2	Identification of karanjin isolated from the Indian beech tree as a potent CYP1 enzyme inhibitor with cellular efficacy
AID1446923	Inhibition of human CYP1A1 expressed in yeast microsomal membranes using 7-ethoxyresorufin/3-cyano-7-ethoxycoumarin as substrate by fluorescence assay	2017	European journal of medicinal chemistry, Apr-21, Volume: 130	Quinazoline derivatives as selective CYP1B1 inhibitors.
AID1583035	Inhibition of CYP1A2 in human liver microsomes using phenacetin substrate in presence of NADPH incubated for 10 mins	2020	Journal of medicinal chemistry, 02-13, Volume: 63, Issue:3	Discovery and Characterization of Fluorine-Substituted Diarylpyrimidine Derivatives as Novel HIV-1 NNRTIs with Highly Improved Resistance Profiles and Low Activity for the hERG Ion Channel.
AID517524	Inhibition of human CYP1A2	2010	Bioorganic & medicinal chemistry letters, Oct-15, Volume: 20, Issue:20	Isoform-selective inhibition of chrysin towards human cytochrome P450 1A2. Kinetics analysis, molecular docking, and molecular dynamics simulations.
AID1688848	Inhibition of recombinant human CYP1A2 expressed in baculovirus infected insect cells using 7-ethoxyresorufin as substrate preincubated for 5 mins followed by NADPH addition and measured after 35 mins by EROD assay	2020	European journal of medicinal chemistry, Mar-01, Volume: 189	Design and synthesis of α-naphthoflavone chimera derivatives able to eliminate cytochrome P450 (CYP)1B1-mediated drug resistance via targeted CYP1B1 degradation.
AID1488363	Inhibition of human CYP1A1 expressed in HEK293 cells using fluorogenic substrate 7-ethoxyresorufin as substrate preincubated for 30 mins followed by substrate addition measured for 60 mins by fluorescence assay	2017	Bioorganic & medicinal chemistry letters, 08-15, Volume: 27, Issue:16	Synthesis and biological evaluation of pyrrole-based chalcones as CYP1 enzyme inhibitors, for possible prevention of cancer and overcoming cisplatin resistance.
AID1372149	Inhibition of human CYP1A expressed in HEK293 cells by fluorescence assay
AID1680603	Inhibition of human CYP1A1 expressed in sacchrosomes using 7-ethoxyresorufin as substrate by fluorescence based assay
AID1680581	Inhibition of human CYP1B1 expressed in sacchrosomes at 10 uM using 7-ethoxyresorufin as substrate by fluorescence based assay relative to control
AID1680587	Cell cycle arrest in human MCF-7 cells over expressing CYP1A1 assessed as down regulation of CyclinD1 after 24 hrs by western blotting assay
AID1488366	Inhibition of human CYP2D6 expressed in HEK293 cells using fluorogenic 7-ethoxy-methyloxy-3-cyanocoumarin as substrate preincubated for 30 mins followed by substrate addition measured for 60 mins by fluorescence assay	2017	Bioorganic & medicinal chemistry letters, 08-15, Volume: 27, Issue:16	Synthesis and biological evaluation of pyrrole-based chalcones as CYP1 enzyme inhibitors, for possible prevention of cancer and overcoming cisplatin resistance.
AID739397	Inhibition of CYP2B1 (unknown origin)-mediated depentylation of resorufin pentyl ether after 5 mins by spectrofluorimetric analysis	2013	Journal of medicinal chemistry, May-23, Volume: 56, Issue:10	Pyranoflavones: a group of small-molecule probes for exploring the active site cavities of cytochrome P450 enzymes 1A1, 1A2, and 1B1.
AID1411732	Inhibition of recombinant human CYP1A2 expressed in baker's yeast-derived microsomes (Sacchrosomes) at 10 uM using 3-cyano-7-ethoxycoumarin substrate by EROD assay relative to control	2018	MedChemComm, Feb-01, Volume: 9, Issue:2	Identification of karanjin isolated from the Indian beech tree as a potent CYP1 enzyme inhibitor with cellular efficacy
AID1446926	Inhibition of human CYP2D6 expressed in yeast microsomal membranes using 7-ethoxy-methyloxy-3-cyanocoumarin as substrate by fluorescence assay	2017	European journal of medicinal chemistry, Apr-21, Volume: 130	Quinazoline derivatives as selective CYP1B1 inhibitors.
AID1203553	Inhibition of human recombinant CYP1B1 expressed in Escherichia coli membranes assessed as reduction in 7-ethoxyresorufin O-deethylation activity	2015	Journal of medicinal chemistry, Apr-23, Volume: 58, Issue:8	Design and Synthesis of New α-Naphthoflavones as Cytochrome P450 (CYP) 1B1 Inhibitors To Overcome Docetaxel-Resistance Associated with CYP1B1 Overexpression.
AID1387227	Inhibition of recombinant human CYP1B1 at 3 uM incubated for 45 mins using 7-ethyl-O-resorufin substrate in presence of NADPH regenerating system by fluorescence based ethoxyresorufin-O-deethylase assay	2018	Journal of medicinal chemistry, 10-25, Volume: 61, Issue:20	Targeting Cytochrome P450 (CYP) 1B1 Enzyme with Four Series of A-Ring Substituted Estrane Derivatives: Design, Synthesis, Inhibitory Activity, and Selectivity.
AID1239151	Selectivity ratio of Ki for human microsomal CYP1A1 to Ki for human microsomal CYP1A2	2015	Journal of medicinal chemistry, Aug-27, Volume: 58, Issue:16	A Ligand-Based Drug Design. Discovery of 4-Trifluoromethyl-7,8-pyranocoumarin as a Selective Inhibitor of Human Cytochrome P450 1A2.
AID321164	Inhibition of human aromatase in placental microsomes	2008	Bioorganic & medicinal chemistry, Feb-01, Volume: 16, Issue:3	New 7,8-benzoflavanones as potent aromatase inhibitors: synthesis and biological evaluation.
AID1239150	Inhibition of human microsomal CYP1B1-dependent ethoxyresorufin-O-deethylase activity by spectrofluorimetric analysis in presence of NADPH regenerating solution	2015	Journal of medicinal chemistry, Aug-27, Volume: 58, Issue:16	A Ligand-Based Drug Design. Discovery of 4-Trifluoromethyl-7,8-pyranocoumarin as a Selective Inhibitor of Human Cytochrome P450 1A2.
AID7002	Maximum rate constant for 7-ethoxycoumarin deethylation in rat liver microsomes exposed to 3-methylcholanthrene at concentration of 50 uM	1981	Journal of medicinal chemistry, Jul, Volume: 24, Issue:7	Effects of 1-arylpyrroles and naphthoflavones upon cytochrome P-450 dependent monooxygenase activities.
AID1771169	Inhibition of CYP1A2 (unknown origin) assessed as activity at 0.001 uM relative to control	2021	Journal of medicinal chemistry, 09-09, Volume: 64, Issue:17	Discovery of
AID1537804	Inhibition of recombinant human CYP1B1 expressed in supersomes using 7-ethoxyresorufin as substrate after 35 mins in presence of NADP+ by EROD assay	2019	MedChemComm, Sep-01, Volume: 10, Issue:9	Development of benzochalcone derivatives as selective CYP1B1 inhibitors and anticancer agents.
AID1441864	Inhibition of human liver CYP1B1 expressed in HEK293 cells using 7-ethoxyresorufin as substrate preincubated for 30 mins followed by substrate addition measured after 60 mins by fluorescence assay	2017	European journal of medicinal chemistry, Mar-31, Volume: 129	Discovery and characterization of novel CYP1B1 inhibitors based on heterocyclic chalcones: Overcoming cisplatin resistance in CYP1B1-overexpressing lines.
AID1372144	Inhibition of recombinant human CYP1A1 expressed in yeast microsomal membranes by fluorescence assay
AID1688847	Inhibition of recombinant human CYP1B1 expressed in baculovirus infected insect cells using 7-ethoxyresorufin as substrate preincubated for 5 mins followed by NADPH addition and measured after 15 mins by EROD assay	2020	European journal of medicinal chemistry, Mar-01, Volume: 189	Design and synthesis of α-naphthoflavone chimera derivatives able to eliminate cytochrome P450 (CYP)1B1-mediated drug resistance via targeted CYP1B1 degradation.
AID1515295	Inhibition of human recombinant CYP1A1 using 7-ethoxyresorufin as substrate after 15 mins in presence of NADPH by EROD assay	2019	Bioorganic & medicinal chemistry, 01-15, Volume: 27, Issue:2	Design and synthesis of selective CYP1B1 inhibitor via dearomatization of α-naphthoflavone.
AID1441868	Inhibition of human CYP1B1 expressed in HEK293 cells assessed as potentiation of cisplatin-induced cytotoxicity by measuring cisplatin EC50 at 0.016 uM by MTT assay (Rvb = 61 +/- 8 uM)	2017	European journal of medicinal chemistry, Mar-31, Volume: 129	Discovery and characterization of novel CYP1B1 inhibitors based on heterocyclic chalcones: Overcoming cisplatin resistance in CYP1B1-overexpressing lines.
AID1372148	Inhibition of recombinant human CYP2D6 expressed in yeast microsomal membranes by fluorescence assay
AID6990	Compound was evaluated for inhibition constant, in liver microsomes from beta-naphthoflavone-exposed rats	1981	Journal of medicinal chemistry, Jul, Volume: 24, Issue:7	Effects of 1-arylpyrroles and naphthoflavones upon cytochrome P-450 dependent monooxygenase activities.
AID1488360	Inhibition of human CYP2C9 bound to yeast microsomal membrane using 3-cyano-7-ethoxycoumarin as substrate after 10 mins by fluorescence assay	2017	Bioorganic & medicinal chemistry letters, 08-15, Volume: 27, Issue:16	Synthesis and biological evaluation of pyrrole-based chalcones as CYP1 enzyme inhibitors, for possible prevention of cancer and overcoming cisplatin resistance.
AID1372153	Inhibition of human CYP2D6 expressed in HEK293 cells by fluorescence assay
AID1203558	Inhibition of human CYP1A2 assessed as reduction in 7-ethoxyresorufin O-deethylation activity by fluorescence based EROD assay	2015	Journal of medicinal chemistry, Apr-23, Volume: 58, Issue:8	Design and Synthesis of New α-Naphthoflavones as Cytochrome P450 (CYP) 1B1 Inhibitors To Overcome Docetaxel-Resistance Associated with CYP1B1 Overexpression.
AID1372142	Inhibition of recombinant human CYP1A1 expressed in yeast microsomal membranes at 10 uM by fluorescence assay relative to control
AID370276	Effect on CYP1A1/CYP1A2 in human liver assessed as 7-ethoxyresorufin O-deethylation at 100 uM relative to control	2006	PLoS medicine, Nov, Volume: 3, Issue:11	OPC-67683, a nitro-dihydro-imidazooxazole derivative with promising action against tuberculosis in vitro and in mice.
AID1437051	Inhibition of porcine cholesterol esterase at 50 nM using para-nitrophenyl butyrate as substrate after 5 mins in presence of sodium taurocholate by spectrophotometric method relative to control	2017	Bioorganic & medicinal chemistry letters, 02-15, Volume: 27, Issue:4	Benzoflavones as cholesterol esterase inhibitors: Synthesis, biological evaluation and docking studies.
AID1488356	Inhibition of human CYP1A1 bound to yeast microsomal membrane using 7-ethoxyresorufin as substrate after 10 mins by fluorescence assay	2017	Bioorganic & medicinal chemistry letters, 08-15, Volume: 27, Issue:16	Synthesis and biological evaluation of pyrrole-based chalcones as CYP1 enzyme inhibitors, for possible prevention of cancer and overcoming cisplatin resistance.
AID1446934	Inhibition of recombinant human CYP1A1 expressed in yeast cells using 7-ethoxyresorufin/3-cyano-7-ethoxycoumarin as substrate by fluorescence assay	2017	European journal of medicinal chemistry, Apr-21, Volume: 130	Quinazoline derivatives as selective CYP1B1 inhibitors.
AID1411734	Inhibition of recombinant human CYP2D6 expressed in baker's yeast-derived microsomes (Sacchrosomes) at 10 uM using 7-ethoxy-methyloxy-3-cyanocoumarin substrate by EROD assay relative to control	2018	MedChemComm, Feb-01, Volume: 9, Issue:2	Identification of karanjin isolated from the Indian beech tree as a potent CYP1 enzyme inhibitor with cellular efficacy
AID1491272	Inhibition of CYP1A2 in human liver microsomes using phenacetin as substrate preincubated for 10 mins followed by NADPH addition measured after 10 mins by LC/MS/MS analysis	2017	European journal of medicinal chemistry, Sep-08, Volume: 137	Design, synthesis and evaluation of aromatic heterocyclic derivatives as potent antifungal agents.
AID241691	Inhibition of DNA dependent protein kinase isolated from HeLa cells	2005	Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2	Selective benzopyranone and pyrimido[2,1-a]isoquinolin-4-one inhibitors of DNA-dependent protein kinase: synthesis, structure-activity studies, and radiosensitization of a human tumor cell line in vitro.
AID1515299	Aqueous solubility of compound in 9:1 PBS/ethanol buffer by shake flask method	2019	Bioorganic & medicinal chemistry, 01-15, Volume: 27, Issue:2	Design and synthesis of selective CYP1B1 inhibitor via dearomatization of α-naphthoflavone.
AID1441869	Inhibition of human liver CYP1B1 expressed in Saccharomyces cerevisiae YY7 microsomal membranes at 1 uM using 7-ethoxyresorufin as substrate after 10 mins by fluorescence assay relative to control	2017	European journal of medicinal chemistry, Mar-31, Volume: 129	Discovery and characterization of novel CYP1B1 inhibitors based on heterocyclic chalcones: Overcoming cisplatin resistance in CYP1B1-overexpressing lines.
AID1515296	Inhibition of human recombinant CYP1A2 using 7-ethoxyresorufin as substrate after 30 mins in presence of NADPH by EROD assay	2019	Bioorganic & medicinal chemistry, 01-15, Volume: 27, Issue:2	Design and synthesis of selective CYP1B1 inhibitor via dearomatization of α-naphthoflavone.
AID1437048	Inhibition of porcine cholesterol esterase at 5 nM using para-nitrophenyl butyrate as substrate after 5 mins in presence of sodium taurocholate by spectrophotometric method relative to control	2017	Bioorganic & medicinal chemistry letters, 02-15, Volume: 27, Issue:4	Benzoflavones as cholesterol esterase inhibitors: Synthesis, biological evaluation and docking studies.
AID1721034	Inhibition of CYP1A2 in human liver microsomes after 20 mins by LC-MS/MS analysis	2020	Journal of medicinal chemistry, 09-10, Volume: 63, Issue:17	Discovery of a Conformationally Constrained Oxazolidinone with Improved Safety and Efficacy Profiles for the Treatment of Multidrug-Resistant Tuberculosis.
AID1441883	Inhibition of human liver CYP1B1 expressed in Saccharomyces cerevisiae YY7 microsomal membranes at 5 to 10 uM using 7-ethoxyresorufin as substrate after 10 mins by fluorescence assay	2017	European journal of medicinal chemistry, Mar-31, Volume: 129	Discovery and characterization of novel CYP1B1 inhibitors based on heterocyclic chalcones: Overcoming cisplatin resistance in CYP1B1-overexpressing lines.
AID1488357	Inhibition of human CYP1B1 bound to yeast microsomal membrane using 7-ethoxyresorufin as substrate after 10 mins by fluorescence assay	2017	Bioorganic & medicinal chemistry letters, 08-15, Volume: 27, Issue:16	Synthesis and biological evaluation of pyrrole-based chalcones as CYP1 enzyme inhibitors, for possible prevention of cancer and overcoming cisplatin resistance.
AID1368060	Inhibition of recombinant human CYP1A2 expressed in HEK293 cells using 3-cyano-7-ethoxycoumarin as substrate pretreated for 30 mins followed by substrate addition measured for 60 mins by fluorescence assay	2017	Bioorganic & medicinal chemistry letters, 12-15, Volume: 27, Issue:24	(E)-3-(3,4,5-Trimethoxyphenyl)-1-(pyridin-4-yl)prop-2-en-1-one, a heterocyclic chalcone is a potent and selective CYP1A1 inhibitor and cancer chemopreventive agent.
AID7012	Maximum rate constant for 7-ethoxycoumarin deethylation in rat liver microsomes exposed to beta-naphthoflavone at 5 uM	1981	Journal of medicinal chemistry, Jul, Volume: 24, Issue:7	Effects of 1-arylpyrroles and naphthoflavones upon cytochrome P-450 dependent monooxygenase activities.
AID1337728	Inhibition of recombinant human CYP1B1 expressed in bacterial microsomes co-expressing P450 reductase at 3 uM using 7-ethyl-O-resorufin as substrate after 45 mins in presence of NADPH by fluorescence assay relative to control	2016	Bioorganic & medicinal chemistry letters, 11-01, Volume: 26, Issue:21	Targeting cytochrome P450 (CYP) 1B1 with steroid derivatives.
AID624613	Specific activity of expressed human recombinant UGT1A10	2000	Annual review of pharmacology and toxicology, , Volume: 40	Human UDP-glucuronosyltransferases: metabolism, expression, and disease.
AID1472627	Inhibition of CYP1A2 in human liver microsomes using phenacetin as substrate upto 10 uM after 10 mins in presence of NADPH by LC-MS/MS analysis	2018	Journal of medicinal chemistry, 01-11, Volume: 61, Issue:1	Novel Terminal Bipheny-Based Diapophytoene Desaturases (CrtN) Inhibitors as Anti-MRSA/VISR/LRSA Agents with Reduced hERG Activity.
AID1446927	Inhibition of human CYP3A4 expressed in yeast microsomal membranes using dibenzylfluorescein as substrate by fluorescence assay	2017	European journal of medicinal chemistry, Apr-21, Volume: 130	Quinazoline derivatives as selective CYP1B1 inhibitors.
AID1387231	Inhibition of recombinant human CYP1A1 incubated for 25 mins using 7-ethyl-O-resorufin substrate in presence of NADPH regenerating system by fluorescence based ethoxyresorufin-O-deethylase assay	2018	Journal of medicinal chemistry, 10-25, Volume: 61, Issue:20	Targeting Cytochrome P450 (CYP) 1B1 Enzyme with Four Series of A-Ring Substituted Estrane Derivatives: Design, Synthesis, Inhibitory Activity, and Selectivity.
AID739409	Inhibition of CYP1A2 (unknown origin)-mediated demethylation of resorufin methyl ether after 5 mins by spectrofluorimetric analysis	2013	Journal of medicinal chemistry, May-23, Volume: 56, Issue:10	Pyranoflavones: a group of small-molecule probes for exploring the active site cavities of cytochrome P450 enzymes 1A1, 1A2, and 1B1.
AID6989	Compound was evaluated for inhibition constant, in liver microsomes from 3-methylcholanthrene-exposed rats	1981	Journal of medicinal chemistry, Jul, Volume: 24, Issue:7	Effects of 1-arylpyrroles and naphthoflavones upon cytochrome P-450 dependent monooxygenase activities.
AID1727622	Inhibition of recombinant human CYP1A2 using 7-ethoxyresorufin as substrate after 50 mins in presence of NADP+ by EROD assay	2021	European journal of medicinal chemistry, Jan-01, Volume: 209	Discovery of heterocycle-containing α-naphthoflavone derivatives as water-soluble, highly potent and selective CYP1B1 inhibitors.
AID1515294	Inhibition of human recombinant CYP1B1 using 7-ethoxyresorufin as substrate after 30 mins in presence of NADPH by EROD assay	2019	Bioorganic & medicinal chemistry, 01-15, Volume: 27, Issue:2	Design and synthesis of selective CYP1B1 inhibitor via dearomatization of α-naphthoflavone.
AID1771170	Inhibition of CYP1A2 (unknown origin) assessed as activity at 0.01 uM relative to control	2021	Journal of medicinal chemistry, 09-09, Volume: 64, Issue:17	Discovery of
AID670547	Inhibition of CYP1A2 at 3 uM	2012	Bioorganic & medicinal chemistry letters, Jul-15, Volume: 22, Issue:14	Synthesis and evaluation of novel potent HCV NS5A inhibitors.
AID1368055	Inhibition of human CYP3A4 expressed in yeast microsomal membranes using dibenzylfluorescein as substrate measured after 10 mins by fluorescence assay	2017	Bioorganic & medicinal chemistry letters, 12-15, Volume: 27, Issue:24	(E)-3-(3,4,5-Trimethoxyphenyl)-1-(pyridin-4-yl)prop-2-en-1-one, a heterocyclic chalcone is a potent and selective CYP1A1 inhibitor and cancer chemopreventive agent.
AID1446928	Inhibition of human CYP2C9 expressed in yeast microsomal membranes using 3-cyano-7-ethoxycoumarin as substrate by fluorescence assay	2017	European journal of medicinal chemistry, Apr-21, Volume: 130	Quinazoline derivatives as selective CYP1B1 inhibitors.
AID1372152	Inhibition of human CYP3A4 expressed in HEK293 cells by fluorescence assay
AID1411735	Inhibition of recombinant human CYP3A4 expressed in baker's yeast-derived microsomes (Sacchrosomes) at 10 uM using dibenzylfluorescein substrate by EROD assay relative to control	2018	MedChemComm, Feb-01, Volume: 9, Issue:2	Identification of karanjin isolated from the Indian beech tree as a potent CYP1 enzyme inhibitor with cellular efficacy
AID1890717	Inhibition of human CYP1A2 at 10 uM incubated for 20 mins in presence of NADPH regenerating system by luminescence assay relative to control	2022	Bioorganic & medicinal chemistry letters, 05-15, Volume: 64	Enteroviral replication inhibition by N-Alkyl triazolopyrimidinone derivatives through a non-capsid binding mode.
AID1727620	Inhibition of recombinant human CYP1B1 using 7-ethoxyresorufin as substrate after 35 mins in presence of NADP+ by EROD assay	2021	European journal of medicinal chemistry, Jan-01, Volume: 209	Discovery of heterocycle-containing α-naphthoflavone derivatives as water-soluble, highly potent and selective CYP1B1 inhibitors.
AID1770972	Inhibition of CYP1A2 in human liver Microsome using phenacetin preincubated for 10 mins followed by NADPH addition and further incubated for 10 mins as substrate by LC-MS/MS analysis relative to control	2021	European journal of medicinal chemistry, Dec-05, Volume: 225	Design, synthesis and evaluation of novel 5-phenylthiophene derivatives as potent fungicidal of Candida albicans and antifungal reagents of fluconazole-resistant fungi.
AID1441859	Inhibition of human CYP1B1 expressed in human A2780 cells assessed as potentiation of cisplatin-induced cytotoxicity by measuring cisplatin EC50 at 0.016 uM by MTT assay (Rvb = 40 +/- 4.9 uM)	2017	European journal of medicinal chemistry, Mar-31, Volume: 129	Discovery and characterization of novel CYP1B1 inhibitors based on heterocyclic chalcones: Overcoming cisplatin resistance in CYP1B1-overexpressing lines.
AID1441873	Inhibition of CYP1A2 in supersomes (unknown origin)	2017	European journal of medicinal chemistry, Mar-31, Volume: 129	Discovery and characterization of novel CYP1B1 inhibitors based on heterocyclic chalcones: Overcoming cisplatin resistance in CYP1B1-overexpressing lines.
AID1368061	Inhibition of recombinant human CYP2D6 expressed in HEK293 cells using 7-ethoxy-methyloxy-3-cyanocoumarin as substrate pretreated for 30 mins followed by substrate addition measured for 60 mins by fluorescence assay	2017	Bioorganic & medicinal chemistry letters, 12-15, Volume: 27, Issue:24	(E)-3-(3,4,5-Trimethoxyphenyl)-1-(pyridin-4-yl)prop-2-en-1-one, a heterocyclic chalcone is a potent and selective CYP1A1 inhibitor and cancer chemopreventive agent.
AID32357	Displacement of specific [3H]PIA binding from adenosine A1 receptor in rat brain membranes.	1996	Journal of medicinal chemistry, Feb-02, Volume: 39, Issue:3	Interactions of flavonoids and other phytochemicals with adenosine receptors.
AID1368053	Inhibition of human CYP2C9 expressed in yeast microsomal membranes using 3-cyano-7-ethoxycoumarin as substrate measured after 10 mins by fluorescence assay	2017	Bioorganic & medicinal chemistry letters, 12-15, Volume: 27, Issue:24	(E)-3-(3,4,5-Trimethoxyphenyl)-1-(pyridin-4-yl)prop-2-en-1-one, a heterocyclic chalcone is a potent and selective CYP1A1 inhibitor and cancer chemopreventive agent.
AID1437049	Inhibition of porcine cholesterol esterase at 10 nM using para-nitrophenyl butyrate as substrate after 5 mins in presence of sodium taurocholate by spectrophotometric method relative to control	2017	Bioorganic & medicinal chemistry letters, 02-15, Volume: 27, Issue:4	Benzoflavones as cholesterol esterase inhibitors: Synthesis, biological evaluation and docking studies.
AID1203555	Inhibition of human recombinant CYP1A1 expressed in Escherichia coli membranes assessed as reduction in 7-ethoxyresorufin O-deethylation activity	2015	Journal of medicinal chemistry, Apr-23, Volume: 58, Issue:8	Design and Synthesis of New α-Naphthoflavones as Cytochrome P450 (CYP) 1B1 Inhibitors To Overcome Docetaxel-Resistance Associated with CYP1B1 Overexpression.
AID589198	Mechanism based inhibition of rabbit cytochrome P450 3A6, partition ratio	2005	Current drug metabolism, Oct, Volume: 6, Issue:5	Cytochrome p450 enzymes mechanism based inhibitors: common sub-structures and reactivity.
AID1368049	Inhibition of human CYP1A1 expressed in yeast microsomal membranes using 7-ethoxyresorufin as substrate measured after 10 mins by fluorescence assay	2017	Bioorganic & medicinal chemistry letters, 12-15, Volume: 27, Issue:24	(E)-3-(3,4,5-Trimethoxyphenyl)-1-(pyridin-4-yl)prop-2-en-1-one, a heterocyclic chalcone is a potent and selective CYP1A1 inhibitor and cancer chemopreventive agent.
AID1680586	Induction of cell cycle arrest in human MCF7 over expressing CYP1A cells assessed as accumulation at G0/G1 phase incubated for 24 hrs by PI staining based flow cytometric analysis (Rvb =54.3 %)
AID1680601	Inhibition of human CYP1A1 expressed in human HEK293 cells using 7-ethoxyresorufin as substrate preincubated for 30 mins followed by substrate additon and measured after 60 mins by fluorescence based assay
AID311072	Inhibition of CYP1B1	2007	Bioorganic & medicinal chemistry, Aug-01, Volume: 15, Issue:15	Targeting cytochrome P450 enzymes: a new approach in anti-cancer drug development.
AID1581702	Inhibition of human recombinant CYP1A2 using 7-ethoxyresorufin as substrate in presence of glucose-6-phosphate, glucose-6-phosphate dehydrogenase and NADPH-generating system incubated for 50 mins by fluorometry	2020	European journal of medicinal chemistry, Feb-01, Volume: 187	Synthesis and structure-activity relationship studies of α-naphthoflavone derivatives as CYP1B1 inhibitors.
AID1446937	Inhibition of recombinant human liver CYP1B1 expressed in HEK293 cells using 7-ethoxyresorufin as substrate pretreated for 30 mins followed by substrate addition measured for 60 mins by EROD assay	2017	European journal of medicinal chemistry, Apr-21, Volume: 130	Quinazoline derivatives as selective CYP1B1 inhibitors.
AID7296	Michaelis-Menten constant for 7-ethoxycoumarin deethylation in rat liver microsomes exposed to 3-methylcholanthrene at a concentration of 10 uM	1981	Journal of medicinal chemistry, Jul, Volume: 24, Issue:7	Effects of 1-arylpyrroles and naphthoflavones upon cytochrome P-450 dependent monooxygenase activities.
AID1533286	Selectivity ratio of IC50 for recombinant human CYP1A1 expressed in Escherichia coli membranes to IC50 for recombinant human CYP1B1 expressed in Escherichia coli membranes	2018	ACS medicinal chemistry letters, Dec-13, Volume: 9, Issue:12	Adaptable Small Ligand of CYP1 Enzymes for Use in Understanding the Structural Features Determining Isoform Selectivity.
AID1727625	Water solubility of compound by HPLC analysis	2021	European journal of medicinal chemistry, Jan-01, Volume: 209	Discovery of heterocycle-containing α-naphthoflavone derivatives as water-soluble, highly potent and selective CYP1B1 inhibitors.
AID30342	Ability to displace [3H]N6-phenylisopropyladenosine binding from adenosine A1 receptor.	1998	Journal of medicinal chemistry, Jan-01, Volume: 41, Issue:1	Flavonoid derivatives as adenosine receptor antagonists: a comparison of the hypothetical receptor binding site based on a comparative molecular field analysis model.
AID1441872	Inhibition of CYP1A1 in supersomes (unknown origin)	2017	European journal of medicinal chemistry, Mar-31, Volume: 129	Discovery and characterization of novel CYP1B1 inhibitors based on heterocyclic chalcones: Overcoming cisplatin resistance in CYP1B1-overexpressing lines.
AID321165	Inhibition of human aromatase in placental microsomes relative to aminogluthetimide	2008	Bioorganic & medicinal chemistry, Feb-01, Volume: 16, Issue:3	New 7,8-benzoflavanones as potent aromatase inhibitors: synthesis and biological evaluation.
AID33936	Affinity at Adenosine A2A receptor in rat striatal membranes by [3H]- CGS 21680 displacement.	1996	Journal of medicinal chemistry, Feb-02, Volume: 39, Issue:3	Interactions of flavonoids and other phytochemicals with adenosine receptors.
AID1874018	Inhibition of human CYP1A2 at 10 uM preincubated for 10 mins followed by NADPH addition and measured after 20 mins by luciferin reagent based luminescence analysis	2022	Bioorganic & medicinal chemistry, 08-15, Volume: 68	Entry inhibition of hepatitis B virus using cyclosporin O derivatives with peptoid side chain incorporation.
AID1895931	Inhibition of CYP1A2 in human liver microsomes incubated for 20 mins in presence of NADPH by LC-MS/MS analysis	2021	Journal of medicinal chemistry, 12-23, Volume: 64, Issue:24	Identification of C5-NH
AID1773465	Inhibition of CYP1A2 in human liver microsomes using phenacetin as substrate in presence of NADPH incubated for 10 mins by LC-MS/MS analysis
AID1813639	Inhibition of CYP1A2 in human liver microsome using phenacetin as substrate	2021	Journal of medicinal chemistry, 12-09, Volume: 64, Issue:23	Synthesis, Characterization, and Preclinical Evaluation of a Small-Molecule Prostate-Specific Membrane Antigen-Targeted Monomethyl Auristatin E Conjugate.
AID1452981	Inhibition of human CYP1A1 expressed in Escherichia coli DH5alpha coexpressing human NADPH P450 reductase using 7-ethoxyresorufin as substrate in presence of NADPH by fluorimetric analysis	2017	European journal of medicinal chemistry, Jul-28, Volume: 135	Inhibitors of cytochrome P450 (CYP) 1B1.
AID1446929	Inhibition of human CYP2C19 expressed in yeast microsomal membranes using 3-cyano-7-ethoxycoumarin as substrate by fluorescence assay	2017	European journal of medicinal chemistry, Apr-21, Volume: 130	Quinazoline derivatives as selective CYP1B1 inhibitors.
AID1372146	Inhibition of recombinant human CYP1A2 expressed in yeast microsomal membranes by fluorescence assay
AID1124619	Stimulation of benzo(alpha)pyrene monooxygenase in phenobarbital-treated Sprague-Dawley rat liver microsomes using [3H]benzo(alpha)pyrene as substrate at 100 uM after 15 mins by liquid scintillation spectrometry	1979	Journal of medicinal chemistry, Oct, Volume: 22, Issue:10	A preliminary structure-activity study of the mixed-function oxidase inhibitor 7,8-benzoflavone.
AID1446924	Inhibition of human CYP1B1 expressed in yeast microsomal membranes using 7-ethoxyresorufin as substrate by fluorescence assay	2017	European journal of medicinal chemistry, Apr-21, Volume: 130	Quinazoline derivatives as selective CYP1B1 inhibitors.
AID1124618	Inhibition of benzo(alpha)pyrene monooxygenase in phenobarbital-treated Sprague-Dawley rat liver microsomes using [3H]benzo(alpha)pyrene as substrate after 15 mins by liquid scintillation spectrometry	1979	Journal of medicinal chemistry, Oct, Volume: 22, Issue:10	A preliminary structure-activity study of the mixed-function oxidase inhibitor 7,8-benzoflavone.
AID1581700	Inhibition of human recombinant CYP1B1 using 7-ethoxyresorufin as substrate in presence of glucose-6-phosphate, glucose-6-phosphate dehydrogenase and NADPH-generating system incubated for 35 mins by fluorometry	2020	European journal of medicinal chemistry, Feb-01, Volume: 187	Synthesis and structure-activity relationship studies of α-naphthoflavone derivatives as CYP1B1 inhibitors.
AID1452987	Inhibition of human CYP1B1 expressed in Escherichia coli DH5alpha coexpressing human NADPH P450 reductase using 7-ethoxyresorufin as substrate in presence of NADP+ by fluorimetric analysis	2017	European journal of medicinal chemistry, Jul-28, Volume: 135	Inhibitors of cytochrome P450 (CYP) 1B1.
AID1124612	Inhibition of benzo(alpha)pyrene monooxygenase in 3-methylcholanthrene-treated Sprague-Dawley rat liver microsomes using [3H]benzo(alpha)pyrene as substrate after 15 mins by liquid scintillation spectrometry	1979	Journal of medicinal chemistry, Oct, Volume: 22, Issue:10	A preliminary structure-activity study of the mixed-function oxidase inhibitor 7,8-benzoflavone.
AID1680600	Inhibition of human CYP1B1 expressed in human HEK293 cells using 7-ethoxyresorufin as substrate preincubated for 30 mins followed by substrate additon and measured after 60 mins by fluorescence based assay
AID1533285	Inhibition of recombinant human CYP1B1 expressed in Escherichia coli membranes co-expressing NADPH-P450 reductase assessed as reduction in ethoxyresorufin O-de-ethylation preincubated for 3 mins followed by NADPH addition and measured after 10 mins by flu	2018	ACS medicinal chemistry letters, Dec-13, Volume: 9, Issue:12	Adaptable Small Ligand of CYP1 Enzymes for Use in Understanding the Structural Features Determining Isoform Selectivity.
AID1488364	Inhibition of human CYP1B1 expressed in HEK293 cells using fluorogenic 7-ethoxyresorufin as substrate preincubated for 30 mins followed by substrate addition measured for 60 mins by fluorescence assay	2017	Bioorganic & medicinal chemistry letters, 08-15, Volume: 27, Issue:16	Synthesis and biological evaluation of pyrrole-based chalcones as CYP1 enzyme inhibitors, for possible prevention of cancer and overcoming cisplatin resistance.
AID7022	Compound was evaluated for alpha -rate constant, in liver microsomes from beta-naphthoflavone-exposed rats	1981	Journal of medicinal chemistry, Jul, Volume: 24, Issue:7	Effects of 1-arylpyrroles and naphthoflavones upon cytochrome P-450 dependent monooxygenase activities.
AID1387229	Inhibition of recombinant human CYP1A1 at 3 uM incubated for 25 mins using 7-ethyl-O-resorufin substrate in presence of NADPH regenerating system by fluorescence based ethoxyresorufin-O-deethylase assay	2018	Journal of medicinal chemistry, 10-25, Volume: 61, Issue:20	Targeting Cytochrome P450 (CYP) 1B1 Enzyme with Four Series of A-Ring Substituted Estrane Derivatives: Design, Synthesis, Inhibitory Activity, and Selectivity.
AID1488365	Inhibition of human CYP1A2 expressed in HEK293 cells using fluorogenic 3-cyano-7-ethoxycoumarin as substrate preincubated for 30 mins followed by substrate addition measured for 60 mins by fluorescence assay	2017	Bioorganic & medicinal chemistry letters, 08-15, Volume: 27, Issue:16	Synthesis and biological evaluation of pyrrole-based chalcones as CYP1 enzyme inhibitors, for possible prevention of cancer and overcoming cisplatin resistance.
AID1441878	Inhibition of human liver CYP1A2 expressed in Saccharomyces cerevisiae YY7 microsomal membranes using CEC as substrate after 10 mins by fluorescence assay	2017	European journal of medicinal chemistry, Mar-31, Volume: 129	Discovery and characterization of novel CYP1B1 inhibitors based on heterocyclic chalcones: Overcoming cisplatin resistance in CYP1B1-overexpressing lines.
AID1446935	Inhibition of recombinant human CYP1B1 expressed in yeast cells using 7-ethoxyresorufin as substrate by fluorescence assay	2017	European journal of medicinal chemistry, Apr-21, Volume: 130	Quinazoline derivatives as selective CYP1B1 inhibitors.
AID7013	Maximum rate constant for 7-ethoxycoumarin deethylation in rat liver microsomes exposed to beta-naphthoflavone at 50 uM	1981	Journal of medicinal chemistry, Jul, Volume: 24, Issue:7	Effects of 1-arylpyrroles and naphthoflavones upon cytochrome P-450 dependent monooxygenase activities.
AID1862951	Inhibition of CYP1A1/2-mediated metabolite formation in rat liver microsomes assessed as reduction in N-(1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)pentadecanamide metabolism	2022	Bioorganic & medicinal chemistry letters, 09-15, Volume: 72	Design, synthesis and antitumor activity study of a gemcitabine prodrug conjugated with a HDAC6 inhibitor.
AID6986	Michaelis-Menten constant for 7-ethoxycoumarin deethylation in rat liver microsomes exposed to beta-naphthoflavone at 50 uM	1981	Journal of medicinal chemistry, Jul, Volume: 24, Issue:7	Effects of 1-arylpyrroles and naphthoflavones upon cytochrome P-450 dependent monooxygenase activities.
AID1203566	Inhibition of CYP1B1 in TCDD-stimulated human MCF7 cells assessed as inhibition of anticancer drug resistance by measuring docetaxel cytotoxic IC50 at 10 uM after 48 hrs by MTT assay (Rvb = 139.8 +/- 11.5 microM)	2015	Journal of medicinal chemistry, Apr-23, Volume: 58, Issue:8	Design and Synthesis of New α-Naphthoflavones as Cytochrome P450 (CYP) 1B1 Inhibitors To Overcome Docetaxel-Resistance Associated with CYP1B1 Overexpression.
AID624610	Specific activity of expressed human recombinant UGT1A7	2000	Annual review of pharmacology and toxicology, , Volume: 40	Human UDP-glucuronosyltransferases: metabolism, expression, and disease.
AID1488369	Inhibition of human CYP3A4 expressed in HEK293 cells using fluorogenic dibenzylfluorescein as substrate preincubated for 30 mins followed by substrate addition measured for 60 mins by fluorescence assay	2017	Bioorganic & medicinal chemistry letters, 08-15, Volume: 27, Issue:16	Synthesis and biological evaluation of pyrrole-based chalcones as CYP1 enzyme inhibitors, for possible prevention of cancer and overcoming cisplatin resistance.
AID1886458	Inhibition of CYP1A2 in human liver microsomes incubated for 10 mins in the presence of NADPH by high performance liquid chromatography-tandem mass spectrometry
AID768691	Inhibition of human BCRP expressed in MDCK2 cells assessed as accumulation of Hoechst 33342 preincubated for 30 mins before Hoechst 33342 addition measured after 120 mins by fluorescence assay	2013	European journal of medicinal chemistry, Sep, Volume: 67	Synthesis and biological evaluation of flavones and benzoflavones as inhibitors of BCRP/ABCG2.
AID1537810	Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viability after 48 hrs by MTT assay	2019	MedChemComm, Sep-01, Volume: 10, Issue:9	Development of benzochalcone derivatives as selective CYP1B1 inhibitors and anticancer agents.
AID1437050	Inhibition of porcine cholesterol esterase at 25 nM using para-nitrophenyl butyrate as substrate after 5 mins in presence of sodium taurocholate by spectrophotometric method relative to control	2017	Bioorganic & medicinal chemistry letters, 02-15, Volume: 27, Issue:4	Benzoflavones as cholesterol esterase inhibitors: Synthesis, biological evaluation and docking studies.
AID1860404	Inhibition of CYP1A2 in human liver microsomes at 10 uM preincubated for 10 mins followed by addition of NADPH-regenerating system and measured after 15 mins by LC-MS/MS analysis relative to control	2022	European journal of medicinal chemistry, Aug-05, Volume: 238	Design, synthesis, and biological evaluation of novel pyrazolo [3,4-d]pyrimidine derivatives as potent PLK4 inhibitors for the treatment of TRIM37-amplified breast cancer.
AID1441871	Inhibition of human CYP1B1 expressed in human AHH1 cells	2017	European journal of medicinal chemistry, Mar-31, Volume: 129	Discovery and characterization of novel CYP1B1 inhibitors based on heterocyclic chalcones: Overcoming cisplatin resistance in CYP1B1-overexpressing lines.
AID7020	Vmax determined by 7-ethoxycoumarin deethylation in the presence by liver microsomes from rats exposed to 3-methylcholanthrene at concentration of 10 uM	1981	Journal of medicinal chemistry, Jul, Volume: 24, Issue:7	Effects of 1-arylpyrroles and naphthoflavones upon cytochrome P-450 dependent monooxygenase activities.
AID1392836	Inhibition of CYP1A2 in human liver microsomes using phenacetin as substrate preincubated for 10 mins followed by NADPH addition measured after 10 mins by LC-MS/MS analysis	2018	Bioorganic & medicinal chemistry, 07-23, Volume: 26, Issue:12	Design, synthesis and evaluation of benzoheterocycle analogues as potent antifungal agents targeting CYP51.
AID1337729	Inhibition of recombinant human CYP1B1 expressed in bacterial microsomes co-expressing P450 reductase using 7-ethyl-O-resorufin as substrate after 45 mins in presence of NADPH by fluorescence assay	2016	Bioorganic & medicinal chemistry letters, 11-01, Volume: 26, Issue:21	Targeting cytochrome P450 (CYP) 1B1 with steroid derivatives.
AID1411736	Inhibition of recombinant human CYP2C9 expressed in baker's yeast-derived microsomes (Sacchrosomes) at 10 uM using 3-cyano-7-ethoxycoumarin substrate by EROD assay relative to control	2018	MedChemComm, Feb-01, Volume: 9, Issue:2	Identification of karanjin isolated from the Indian beech tree as a potent CYP1 enzyme inhibitor with cellular efficacy
AID1203556	Inhibition of human CYP1B1 assessed as reduction in 7-ethoxyresorufin O-deethylation activity by fluorescence based EROD assay	2015	Journal of medicinal chemistry, Apr-23, Volume: 58, Issue:8	Design and Synthesis of New α-Naphthoflavones as Cytochrome P450 (CYP) 1B1 Inhibitors To Overcome Docetaxel-Resistance Associated with CYP1B1 Overexpression.
AID378537	Inhibition of TCDD-induced EROD activity in human HepG2 cells after 24 hrs	2005	Journal of natural products, Mar, Volume: 68, Issue:3	Bisindigotin, a TCDD antagonist from the Chinese medicinal herb Isatis indigotica.
AID1368052	Inhibition of human CYP2D6 expressed in yeast microsomal membranes using 7-ethoxy-methyloxy-3-cyanocoumarin as substrate measured after 10 mins by fluorescence assay	2017	Bioorganic & medicinal chemistry letters, 12-15, Volume: 27, Issue:24	(E)-3-(3,4,5-Trimethoxyphenyl)-1-(pyridin-4-yl)prop-2-en-1-one, a heterocyclic chalcone is a potent and selective CYP1A1 inhibitor and cancer chemopreventive agent.
AID1368062	Inhibition of recombinant human CYP2C9 expressed in HEK293 cells using 3-cyano-7-ethoxycoumarin as substrate pretreated for 30 mins followed by substrate addition measured for 60 mins by fluorescence assay	2017	Bioorganic & medicinal chemistry letters, 12-15, Volume: 27, Issue:24	(E)-3-(3,4,5-Trimethoxyphenyl)-1-(pyridin-4-yl)prop-2-en-1-one, a heterocyclic chalcone is a potent and selective CYP1A1 inhibitor and cancer chemopreventive agent.
AID768684	Inhibition of p-glycoprotein (unknown origin) expressed in human A2780Adr cells assessed as calcein-AM accumulation preincubated for 30 mins before calcein-AM addition measured up to 90 mins by fluorescence assay	2013	European journal of medicinal chemistry, Sep, Volume: 67	Synthesis and biological evaluation of flavones and benzoflavones as inhibitors of BCRP/ABCG2.
AID1680602	Inhibition of human CYP1B1 expressed in sacchrosomes using 7-ethoxyresorufin as substrate by fluorescence based assay
AID1441876	Inhibition of human liver CYP1B1 expressed in Saccharomyces cerevisiae YY7 microsomal membranes using 7-ethoxyresorufin as substrate after 10 mins by fluorescence assay	2017	European journal of medicinal chemistry, Mar-31, Volume: 129	Discovery and characterization of novel CYP1B1 inhibitors based on heterocyclic chalcones: Overcoming cisplatin resistance in CYP1B1-overexpressing lines.
AID589148	Mechanism based inhibition of human cytochrome P450 3A4 measured by testosterone 6-beta hydroxylation	2005	Current drug metabolism, Oct, Volume: 6, Issue:5	Cytochrome p450 enzymes mechanism based inhibitors: common sub-structures and reactivity.
AID1701906	Inhibition of CYP1A2 in human liver microsomes at 10 uM using phenacetin as substrate preincubated for 5 mins followed by NADPH addition and measured after 20 mins by LC-MS/MS analysis relative to control	2016	Journal of medicinal chemistry, 12-08, Volume: 59, Issue:23	Novel Tetrahydropyrido[4,3-d]pyrimidines as Potent Inhibitors of Chaperone Heat Shock Protein 90.
AID1880382	Inhibition of CYP1A2 in human liver microsomes using phenacetin as substrate incubated for 15 to 45 mins in presence of NADPH	2022	Journal of medicinal chemistry, 06-23, Volume: 65, Issue:12	Structure-Based Discovery of Novel NH
AID311073	Inhibition of CYP1A1	2007	Bioorganic & medicinal chemistry, Aug-01, Volume: 15, Issue:15	Targeting cytochrome P450 enzymes: a new approach in anti-cancer drug development.
AID1203557	Inhibition of human CYP1A1 assessed as reduction in 7-ethoxyresorufin O-deethylation activity by fluorescence based EROD assay	2015	Journal of medicinal chemistry, Apr-23, Volume: 58, Issue:8	Design and Synthesis of New α-Naphthoflavones as Cytochrome P450 (CYP) 1B1 Inhibitors To Overcome Docetaxel-Resistance Associated with CYP1B1 Overexpression.
AID1446941	Inhibition of recombinant human CYP1B1 expressed in Escherichia coli DH5[alpha] using 7-ethoxyresorufin/3-cyano-7-ethoxycoumarin as substrate in presence of NADPH by EROD assay	2017	European journal of medicinal chemistry, Apr-21, Volume: 130	Quinazoline derivatives as selective CYP1B1 inhibitors.
AID1676232	Inhibition of CYP1A2 in human liver microsome using probe substrate measured after 20 mins in presence of NADPH by LC-MS/MS analysis	2020	Journal of medicinal chemistry, 10-08, Volume: 63, Issue:19	Novel Human Urate Transporter 1 Inhibitors as Hypouricemic Drug Candidates with Favorable Druggability.
AID1441865	Inhibition of human liver CYP1B1 expressed in HEK293 cells using CEC as substrate preincubated for 30 mins followed by substrate addition measured after 60 mins by fluorescence assay	2017	European journal of medicinal chemistry, Mar-31, Volume: 129	Discovery and characterization of novel CYP1B1 inhibitors based on heterocyclic chalcones: Overcoming cisplatin resistance in CYP1B1-overexpressing lines.
AID1441863	Solubility of the compound in pH 6.8 simulated intestinal fluid	2017	European journal of medicinal chemistry, Mar-31, Volume: 129	Discovery and characterization of novel CYP1B1 inhibitors based on heterocyclic chalcones: Overcoming cisplatin resistance in CYP1B1-overexpressing lines.
AID1533287	Selectivity ratio of IC50 for recombinant human CYP1A1 expressed in Escherichia coli membranes to IC50 for recombinant human CYP1A2 expressed in Escherichia coli membranes	2018	ACS medicinal chemistry letters, Dec-13, Volume: 9, Issue:12	Adaptable Small Ligand of CYP1 Enzymes for Use in Understanding the Structural Features Determining Isoform Selectivity.
AID7300	Michaelis-Menten constant for 7-ethoxycoumarin deethylation in rat liver microsomes exposed to 3-methylcholanthrene at a concentration of 50 uM	1981	Journal of medicinal chemistry, Jul, Volume: 24, Issue:7	Effects of 1-arylpyrroles and naphthoflavones upon cytochrome P-450 dependent monooxygenase activities.
AID1372145	Inhibition of human CYP1B1 expressed in yeast microsomal membranes using 7-ethoxyresorufin as substrate by fluorescence assay
AID1181465	Inhibition of recombinant human CYP1A2 preincubated at 10 uM for 5 mins before fluorescent substrate addition by fluorescence assay	2014	Bioorganic & medicinal chemistry letters, Aug-01, Volume: 24, Issue:15	Synthesis and biological evaluation of 3-phenethylazetidine derivatives as triple reuptake inhibitors.
AID589172	Mechanism based inhibition of rabbit cytochrome P450 3A6 measured by testosterone and progesterone 6-beta hydroxylation	2005	Current drug metabolism, Oct, Volume: 6, Issue:5	Cytochrome p450 enzymes mechanism based inhibitors: common sub-structures and reactivity.
AID1901573	Inhibition of CYP1A2 in human liver microsomes in presence of NADPH incubated for 3 to 20 mins by LC-MS/MS analysis	2022	Journal of medicinal chemistry, 03-10, Volume: 65, Issue:5	Discovery of Novel Bicyclic Imidazolopyridine-Containing Human Urate Transporter 1 Inhibitors as Hypouricemic Drug Candidates with Improved Efficacy and Favorable Druggability.
AID6985	Michaelis-Menten constant for 7-ethoxycoumarin deethylation in rat liver microsomes exposed to beta-naphthoflavone at 5 uM	1981	Journal of medicinal chemistry, Jul, Volume: 24, Issue:7	Effects of 1-arylpyrroles and naphthoflavones upon cytochrome P-450 dependent monooxygenase activities.
AID1488359	Inhibition of human CYP2D6 bound to yeast microsomal membrane using 7-ethoxy-methyloxy-3-cyanocoumarin as substrate after 10 mins by fluorescence assay	2017	Bioorganic & medicinal chemistry letters, 08-15, Volume: 27, Issue:16	Synthesis and biological evaluation of pyrrole-based chalcones as CYP1 enzyme inhibitors, for possible prevention of cancer and overcoming cisplatin resistance.
AID739410	Inhibition of CYP1A1 (unknown origin)-mediated deethylation of resorufin ethyl ether after 5 mins by spectrofluorimetric analysis	2013	Journal of medicinal chemistry, May-23, Volume: 56, Issue:10	Pyranoflavones: a group of small-molecule probes for exploring the active site cavities of cytochrome P450 enzymes 1A1, 1A2, and 1B1.
AID34263	Displacement of specific [125I]AB-MECA binding from human Adenosine A3 receptor expressed in HEK293 cells	1996	Journal of medicinal chemistry, Feb-02, Volume: 39, Issue:3	Interactions of flavonoids and other phytochemicals with adenosine receptors.
AID1637837	Inhibition of bovine milk xanthine oxidase using xanthine as substrate preincubated for 5 mins followed by substrate addition by UV-visible spectrophotometry	2019	MedChemComm, Jan-01, Volume: 10, Issue:1	Benzoflavone derivatives as potent antihyperuricemic agents.
AID1533283	Inhibition of recombinant human CYP1A1 expressed in Escherichia coli membranes co-expressing NADPH-P450 reductase assessed as reduction in ethoxyresorufin O-de-ethylation preincubated for 3 mins followed by NADPH addition and measured after 10 mins by flu	2018	ACS medicinal chemistry letters, Dec-13, Volume: 9, Issue:12	Adaptable Small Ligand of CYP1 Enzymes for Use in Understanding the Structural Features Determining Isoform Selectivity.
AID33150	Ability to displace [3H]-CGS- 21680 binding from adenosine A2A receptor.	1998	Journal of medicinal chemistry, Jan-01, Volume: 41, Issue:1	Flavonoid derivatives as adenosine receptor antagonists: a comparison of the hypothetical receptor binding site based on a comparative molecular field analysis model.
AID1515292	Inhibition of human recombinant CYP1A1 using 7-ethoxyresorufin as substrate assessed as percent enzyme activity at 1 uM after 15 mins in presence of NADPH by EROD assay relative to control	2019	Bioorganic & medicinal chemistry, 01-15, Volume: 27, Issue:2	Design and synthesis of selective CYP1B1 inhibitor via dearomatization of α-naphthoflavone.
AID1727624	Selectivity index, ratio of IC50 for recombinant human CYP1A2 to IC50 for recombinant human CYP1B1	2021	European journal of medicinal chemistry, Jan-01, Volume: 209	Discovery of heterocycle-containing α-naphthoflavone derivatives as water-soluble, highly potent and selective CYP1B1 inhibitors.
AID1537805	Inhibition of recombinant human CYP1A1 expressed in supersomes using 7-ethoxyresorufin as substrate after 15 mins in presence of NADP+ by EROD assay	2019	MedChemComm, Sep-01, Volume: 10, Issue:9	Development of benzochalcone derivatives as selective CYP1B1 inhibitors and anticancer agents.
AID1680582	Inhibition of human CYP1A1 expressed in sacchrosomes at 10 uM using 7-ethoxyresorufin as substrate by fluorescence based assay relative to control
AID1488368	Inhibition of human CYP2C19 expressed in HEK293 cells using fluorogenic 3-cyano-7-ethoxycoumarin as substrate preincubated for 30 mins followed by substrate addition measured for 60 mins by fluorescence assay	2017	Bioorganic & medicinal chemistry letters, 08-15, Volume: 27, Issue:16	Synthesis and biological evaluation of pyrrole-based chalcones as CYP1 enzyme inhibitors, for possible prevention of cancer and overcoming cisplatin resistance.
AID1450069	Inhibition of recombinant human CYP1A2 expressed in insect cells at 1 uM using EOMCC as substrate pretreated for 10 mins followed by substrate addition measured every minute for 15 mins in presence of NADP+ by fluorescence assay relative to control	2017	Bioorganic & medicinal chemistry letters, 06-01, Volume: 27, Issue:11	Cytochrome P450 binding studies of novel tacrine derivatives: Predicting the risk of hepatotoxicity.
AID1452984	Inhibition of human CYP1A2 expressed in Escherichia coli DH5alpha coexpressing human NADPH P450 reductase in using 7-ethoxyresorufin as substrate in presence of NADPH by fluorimetric analysis	2017	European journal of medicinal chemistry, Jul-28, Volume: 135	Inhibitors of cytochrome P450 (CYP) 1B1.
AID739405	Inhibition of CYP1B1 (unknown origin)-mediated deethylation of resorufin ethyl ether after 5 mins by spectrofluorimetric analysis	2013	Journal of medicinal chemistry, May-23, Volume: 56, Issue:10	Pyranoflavones: a group of small-molecule probes for exploring the active site cavities of cytochrome P450 enzymes 1A1, 1A2, and 1B1.
AID1488358	Inhibition of human CYP1A2 bound to yeast microsomal membrane using 3-cyano-7-ethoxycoumarin as substrate after 10 mins by fluorescence assay	2017	Bioorganic & medicinal chemistry letters, 08-15, Volume: 27, Issue:16	Synthesis and biological evaluation of pyrrole-based chalcones as CYP1 enzyme inhibitors, for possible prevention of cancer and overcoming cisplatin resistance.
AID1372154	Inhibition of human CYP1B1 expressed in MDA-MB-468 cells assessed as cell toxicity
AID280103	Inhibition of beta-naphthoflavone-induced Cyp1A in rat H4II7 cell	2007	Journal of natural products, Mar, Volume: 70, Issue:3	Potential cancer chemopreventive in vitro activities of monomeric xanthone derivatives from the marine algicolous fungus Monodictys putredinis.
AID1515300	Solubility of compound in pH 7.4 PBS by shake flask met	2019	Bioorganic & medicinal chemistry, 01-15, Volume: 27, Issue:2	Design and synthesis of selective CYP1B1 inhibitor via dearomatization of α-naphthoflavone.
AID1452980	Inhibition of human CYP1B1 expressed in Escherichia coli DH5alpha coexpressing human NADPH P450 reductase using 7-ethoxyresorufin as substrate in presence of NADPH by fluorimetric analysis	2017	European journal of medicinal chemistry, Jul-28, Volume: 135	Inhibitors of cytochrome P450 (CYP) 1B1.
AID1368064	Inhibition of recombinant human CYP3A4 expressed in HEK293 cells using dibenzylfluorescein as substrate pretreated for 30 mins followed by substrate addition measured for 60 mins by fluorescence assay	2017	Bioorganic & medicinal chemistry letters, 12-15, Volume: 27, Issue:24	(E)-3-(3,4,5-Trimethoxyphenyl)-1-(pyridin-4-yl)prop-2-en-1-one, a heterocyclic chalcone is a potent and selective CYP1A1 inhibitor and cancer chemopreventive agent.
AID1533284	Inhibition of recombinant human CYP1A2 expressed in Escherichia coli membranes co-expressing NADPH-P450 reductase assessed as reduction in ethoxyresorufin O-de-ethylation preincubated for 3 mins followed by NADPH addition and measured after 10 mins by flu	2018	ACS medicinal chemistry letters, Dec-13, Volume: 9, Issue:12	Adaptable Small Ligand of CYP1 Enzymes for Use in Understanding the Structural Features Determining Isoform Selectivity.
AID1561731	Inhibition of CYP1A2 in human liver microsomes using phenacetin substrate incubated for 10 mins in presence of NADPH
AID1203554	Inhibition of human recombinant CYP1A2 expressed in Escherichia coli membranes assessed as reduction in 7-ethoxyresorufin O-deethylation activity	2015	Journal of medicinal chemistry, Apr-23, Volume: 58, Issue:8	Design and Synthesis of New α-Naphthoflavones as Cytochrome P450 (CYP) 1B1 Inhibitors To Overcome Docetaxel-Resistance Associated with CYP1B1 Overexpression.
AID1515291	Inhibition of human recombinant CYP1B1 using 7-ethoxyresorufin as substrate assessed as percent enzyme activity at 1 uM after 30 mins in presence of NADPH by EROD assay relative to control	2019	Bioorganic & medicinal chemistry, 01-15, Volume: 27, Issue:2	Design and synthesis of selective CYP1B1 inhibitor via dearomatization of α-naphthoflavone.
AID216252	In vitro inhibitory activity against the growth of WISH cell derived from human cervical carcinoma was determined; slight effect	2004	Bioorganic & medicinal chemistry letters, Jan-05, Volume: 14, Issue:1	Antiproliferative activity of various flavonoids and related compounds: additive effect of interferon-alpha2b.
AID1680585	Induction of cell cycle arrest in human MCF7 over expressing CYP1A cells assessed as accumulation at S phase incubated for 24 hrs by PI staining based flow cytometric analysis (Rvb = 20.1%)
AID33196	Ability to displace [125I]AB-MECA binding from adenosine A3 receptor.	1998	Journal of medicinal chemistry, Jan-01, Volume: 41, Issue:1	Flavonoid derivatives as adenosine receptor antagonists: a comparison of the hypothetical receptor binding site based on a comparative molecular field analysis model.
AID1372156	Inhibition of human CYP1B1 expressed in MDA-MB-468 cells assessed as potentiation of cisplatin-induced cytotoxicity by measuring cisplatin EC50 at 20 uM (Rvb = 6.70+/- 0.7 uM)
AID1537811	Cytotoxicity against drug-resistant human MDA-MB-435/LCC6MDR1 cells assessed as reduction in cell viability after 48 hrs by MTT assay	2019	MedChemComm, Sep-01, Volume: 10, Issue:9	Development of benzochalcone derivatives as selective CYP1B1 inhibitors and anticancer agents.
AID1387226	Inhibition of recombinant human CYP1B1 at 0.3 uM incubated for 45 mins using 7-ethyl-O-resorufin substrate in presence of NADPH regenerating system by fluorescence based ethoxyresorufin-O-deethylase assay	2018	Journal of medicinal chemistry, 10-25, Volume: 61, Issue:20	Targeting Cytochrome P450 (CYP) 1B1 Enzyme with Four Series of A-Ring Substituted Estrane Derivatives: Design, Synthesis, Inhibitory Activity, and Selectivity.
AID1488367	Inhibition of human CYP2C9 expressed in HEK293 cells using fluorogenic 3-cyano-7-ethoxycoumarin as preincubated for 30 mins followed by substrate addition measured for 60 mins by fluorescence assay	2017	Bioorganic & medicinal chemistry letters, 08-15, Volume: 27, Issue:16	Synthesis and biological evaluation of pyrrole-based chalcones as CYP1 enzyme inhibitors, for possible prevention of cancer and overcoming cisplatin resistance.
AID1515293	Inhibition of human recombinant CYP1A2 using 7-ethoxyresorufin as substrate assessed as percent enzyme activity at 1 uM after 30 mins in presence of NADPH by EROD assay relative to control	2019	Bioorganic & medicinal chemistry, 01-15, Volume: 27, Issue:2	Design and synthesis of selective CYP1B1 inhibitor via dearomatization of α-naphthoflavone.
AID1387228	Inhibition of recombinant human CYP1A1 at 0.3 uM incubated for 25 mins using 7-ethyl-O-resorufin substrate in presence of NADPH regenerating system by fluorescence based ethoxyresorufin-O-deethylase assay	2018	Journal of medicinal chemistry, 10-25, Volume: 61, Issue:20	Targeting Cytochrome P450 (CYP) 1B1 Enzyme with Four Series of A-Ring Substituted Estrane Derivatives: Design, Synthesis, Inhibitory Activity, and Selectivity.
AID1488362	Inhibition of human CYP3A4 bound to yeast microsomal membrane using dibenzylfluorescein as substrate after 10 mins by fluorescence assay	2017	Bioorganic & medicinal chemistry letters, 08-15, Volume: 27, Issue:16	Synthesis and biological evaluation of pyrrole-based chalcones as CYP1 enzyme inhibitors, for possible prevention of cancer and overcoming cisplatin resistance.
AID1181450	Inhibition of recombinant human CYP1A2 preincubated for 5 mins before fluorescent substrate addition by fluorescence assay	2014	Bioorganic & medicinal chemistry letters, Aug-01, Volume: 24, Issue:15	Synthesis and biological evaluation of 3-phenethylazetidine derivatives as triple reuptake inhibitors.
AID479369	Inhibition of human placental microsome CYP19	2010	Bioorganic & medicinal chemistry letters, May-15, Volume: 20, Issue:10	Pharmacophore modeling strategies for the development of novel nonsteroidal inhibitors of human aromatase (CYP19).
AID1911189	Inhibition of CYP1A2 in human liver microsomes using phenacetin as substrate incubated for 5 to 45 mins in presence of NADPH by LC/MS analysis
AID1203559	Selectivity index, ratio of IC50 for human CYP1A1 to IC50 for human CYP1B1	2015	Journal of medicinal chemistry, Apr-23, Volume: 58, Issue:8	Design and Synthesis of New α-Naphthoflavones as Cytochrome P450 (CYP) 1B1 Inhibitors To Overcome Docetaxel-Resistance Associated with CYP1B1 Overexpression.
AID1203560	Selectivity index, ratio of IC50 for human CYP1A2 to IC50 for human CYP1B1	2015	Journal of medicinal chemistry, Apr-23, Volume: 58, Issue:8	Design and Synthesis of New α-Naphthoflavones as Cytochrome P450 (CYP) 1B1 Inhibitors To Overcome Docetaxel-Resistance Associated with CYP1B1 Overexpression.
AID1572079	Inhibition of CYP1A2 in human liver microsomes using phenacetin as substrate after 10 mins in presence of NADPH	2019	Journal of medicinal chemistry, 02-14, Volume: 62, Issue:3	Identification of Dihydrofuro[3,4- d]pyrimidine Derivatives as Novel HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors with Promising Antiviral Activities and Desirable Physicochemical Properties.
AID1537807	Selectivity index, ratio of IC50 for recombinant human CYP1A1 expressed in supersomes to IC50 for recombinant human CYP1B1 expressed in supersomes	2019	MedChemComm, Sep-01, Volume: 10, Issue:9	Development of benzochalcone derivatives as selective CYP1B1 inhibitors and anticancer agents.
AID1781975	Inhibition of CYP1A2 in human liver microsomes using phenacetin as substrate incubated for 10 mins in presence of NADPH by LC-MS/MS analysis	2021	Journal of medicinal chemistry, 11-11, Volume: 64, Issue:21	Discovery of 1-Amino-1
AID1504638	Inhibition of recombinant human CYP1B1 expressed in supersomes coexpressing P450 reductase using 7-ethyl-O-resorufin as substrate after 45 mins in presence of NADPH by fluorescence assay	2017	ACS medicinal chemistry letters, Nov-09, Volume: 8, Issue:11	Structure-Based Design and Synthesis of New Estrane-Pyridine Derivatives as Cytochrome P450 (CYP) 1B1 Inhibitors.
AID1368080	Inhibition of recombinant human CYP1A1 expressed in HEK293 cells assessed as reduction in benzo(a)pyrene-induced toxicity by measuring increase in B[a]P EC50 at 2 times IC50 by MTT assay	2017	Bioorganic & medicinal chemistry letters, 12-15, Volume: 27, Issue:24	(E)-3-(3,4,5-Trimethoxyphenyl)-1-(pyridin-4-yl)prop-2-en-1-one, a heterocyclic chalcone is a potent and selective CYP1A1 inhibitor and cancer chemopreventive agent.
AID1727621	Inhibition of recombinant human CYP1A1 using 7-ethoxyresorufin as substrate after 15 mins in presence of NADP+ by EROD assay	2021	European journal of medicinal chemistry, Jan-01, Volume: 209	Discovery of heterocycle-containing α-naphthoflavone derivatives as water-soluble, highly potent and selective CYP1B1 inhibitors.
AID7001	Maximum rate constant for 7-ethoxycoumarin deethylation in rat liver microsomes exposed to 3-methylcholanthrene at concentration of 25 uM	1981	Journal of medicinal chemistry, Jul, Volume: 24, Issue:7	Effects of 1-arylpyrroles and naphthoflavones upon cytochrome P-450 dependent monooxygenase activities.
AID1515298	Selectivity ratio of IC50 for human recombinant CYP1A2 to IC50 for human recombinant CYP1B1	2019	Bioorganic & medicinal chemistry, 01-15, Volume: 27, Issue:2	Design and synthesis of selective CYP1B1 inhibitor via dearomatization of α-naphthoflavone.
AID1411730	Inhibition of recombinant human CYP1A1 expressed in baker's yeast-derived microsomes (Sacchrosomes) at 10 uM using 7-ethoxyresorufin substrate by EROD assay relative to control	2018	MedChemComm, Feb-01, Volume: 9, Issue:2	Identification of karanjin isolated from the Indian beech tree as a potent CYP1 enzyme inhibitor with cellular efficacy
AID1811055	Inhibition of human CYP1A2 using phenacetin as substrate in presence of NADPH incubated for 15 to 45 mins	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	Improving Druggability of Novel Diarylpyrimidine NNRTIs by a Fragment-Based Replacement Strategy: From Biphenyl-DAPYs to Heteroaromatic-Biphenyl-DAPYs.
AID1372157	Inhibition of human CYP1A1 transfected in HEK293 cells assessed as protection against CYP1A1 mediated B[a]P toxicity by measuring B[a]P EC50 at 20 uM by MTT assay (Rvb =1.2+/- 0.3 uM)
AID1368063	Inhibition of recombinant human CYP2C19 expressed in HEK293 cells using 3-cyano-7-ethoxycoumarin as substrate pretreated for 30 mins followed by substrate addition measured for 60 mins by fluorescence assay	2017	Bioorganic & medicinal chemistry letters, 12-15, Volume: 27, Issue:24	(E)-3-(3,4,5-Trimethoxyphenyl)-1-(pyridin-4-yl)prop-2-en-1-one, a heterocyclic chalcone is a potent and selective CYP1A1 inhibitor and cancer chemopreventive agent.
AID1446936	Inhibition of recombinant human liver CYP1A1 expressed in HEK293 cells using 7-ethoxyresorufin as substrate pretreated for 30 mins followed by substrate addition measured for 60 mins by EROD assay	2017	European journal of medicinal chemistry, Apr-21, Volume: 130	Quinazoline derivatives as selective CYP1B1 inhibitors.
AID1537809	Cytotoxicity against human MCF7 cells assessed as reduction in cell viability after 48 hrs by MTT assay	2019	MedChemComm, Sep-01, Volume: 10, Issue:9	Development of benzochalcone derivatives as selective CYP1B1 inhibitors and anticancer agents.
AID7299	Michaelis-Menten constant for 7-ethoxycoumarin deethylation in rat liver microsomes exposed to 3-methylcholanthrene at a concentration of 25 uM	1981	Journal of medicinal chemistry, Jul, Volume: 24, Issue:7	Effects of 1-arylpyrroles and naphthoflavones upon cytochrome P-450 dependent monooxygenase activities.
AID1072935	Inhibition of CYP1A2 (unknown origin) at 10 uM relative to control	2014	ACS medicinal chemistry letters, Mar-13, Volume: 5, Issue:3	Potent Hepatitis C Virus NS5A Inhibitors Containing a Benzidine Core.
AID1537812	Cytotoxicity against drug-resistant TCCD-induced human MCF7 cells overexpressing CYP1B1 assessed as reduction in cell viability after 48 hrs by MTT assay	2019	MedChemComm, Sep-01, Volume: 10, Issue:9	Development of benzochalcone derivatives as selective CYP1B1 inhibitors and anticancer agents.
AID622584	Inhibition of NF-kappaB activation expressed in HCT116 cells assessed as inhibition of TNF-alpha-induced transcriptional activation at 10 uM after 12 hrs by luciferase reporter gene assay relative to control	2011	Bioorganic & medicinal chemistry letters, Oct-15, Volume: 21, Issue:20	Relationship between the structures of flavonoids and their NF-κB-dependent transcriptional activities.
AID1372147	Inhibition of recombinant human CYP3A4 expressed in yeast microsomal membranes by fluorescence assay
AID739398	Inhibition of CYP2A6 (unknown origin)-mediated coumarin 7-hydroxylation after 5 mins by spectrofluorimetric analysis	2013	Journal of medicinal chemistry, May-23, Volume: 56, Issue:10	Pyranoflavones: a group of small-molecule probes for exploring the active site cavities of cytochrome P450 enzymes 1A1, 1A2, and 1B1.
AID1581703	Selectivity index, ratio of IC50 for human recombinant CYP1A1 to IC50 for human recombinant CYP1B1 using 7-ethoxyresorufin as substrate in presence of glucose-6-phosphate, glucose-6-phosphate dehydrogenase and NADPH-generating system by fluorometry	2020	European journal of medicinal chemistry, Feb-01, Volume: 187	Synthesis and structure-activity relationship studies of α-naphthoflavone derivatives as CYP1B1 inhibitors.
AID768689	Inhibition of human BCRP expressed in MDCK2 cells assessed as accumulation of pheophorbide-A preincubated for 30 mins before pheophorbide-A addition measured after 120 mins by flow cytometry	2013	European journal of medicinal chemistry, Sep, Volume: 67	Synthesis and biological evaluation of flavones and benzoflavones as inhibitors of BCRP/ABCG2.
AID1581704	Selectivity index, ratio of IC50 for human recombinant CYP1A2 to IC50 for human recombinant CYP1B1 using 7-ethoxyresorufin as substrate in presence of glucose-6-phosphate, glucose-6-phosphate dehydrogenase and NADPH-generating system by fluorometry	2020	European journal of medicinal chemistry, Feb-01, Volume: 187	Synthesis and structure-activity relationship studies of α-naphthoflavone derivatives as CYP1B1 inhibitors.
AID768683	Inhibition of MRP1 (unknown origin) expressed in human 2008 cells assessed as calcein-AM accumulation preincubated for 30 mins before calcein-AM addition measured up to 90 mins by fluorescence assay	2013	European journal of medicinal chemistry, Sep, Volume: 67	Synthesis and biological evaluation of flavones and benzoflavones as inhibitors of BCRP/ABCG2.
AID1688849	Selectivity ratio IC50 for inhibition of recombinant human CYP1A2 to inhibition of recombinant human CYP1B1	2020	European journal of medicinal chemistry, Mar-01, Volume: 189	Design and synthesis of α-naphthoflavone chimera derivatives able to eliminate cytochrome P450 (CYP)1B1-mediated drug resistance via targeted CYP1B1 degradation.
AID1637839	Antioxidant activity assessed as DPPH radical scavenging activity shaken for 1 min and incubated under dark condition for 30 mins by spectrophotometric analysis	2019	MedChemComm, Jan-01, Volume: 10, Issue:1	Benzoflavone derivatives as potent antihyperuricemic agents.
AID1301343	Inhibition of CYP1A2 (unknown origin) at 4 uM by P450-glo assay	2016	Bioorganic & medicinal chemistry, 07-01, Volume: 24, Issue:13	Novel free fatty acid receptor 1 (GPR40) agonists based on 1,3,4-thiadiazole-2-carboxamide scaffold.
AID7021	Compound was evaluated for alpha -rate constant, in liver microsomes from 3-methylcholanthrene-exposed rats	1981	Journal of medicinal chemistry, Jul, Volume: 24, Issue:7	Effects of 1-arylpyrroles and naphthoflavones upon cytochrome P-450 dependent monooxygenase activities.
AID1572368	Inhibition of human CYP1A2 in human liver microsomes at 50 times IC50 concentration relative to control	2019	Journal of medicinal chemistry, 02-14, Volume: 62, Issue:3	Synthesis and Biological Investigation of Phenothiazine-Based Benzhydroxamic Acids as Selective Histone Deacetylase 6 Inhibitors.
AID1441861	Solubility of the compound in pH 7.4 PBS buffer	2017	European journal of medicinal chemistry, Mar-31, Volume: 129	Discovery and characterization of novel CYP1B1 inhibitors based on heterocyclic chalcones: Overcoming cisplatin resistance in CYP1B1-overexpressing lines.
AID1581701	Inhibition of human recombinant CYP1A1 using 7-ethoxyresorufin as substrate in presence of glucose-6-phosphate, glucose-6-phosphate dehydrogenase and NADPH-generating system incubated for 15 mins by fluorometry	2020	European journal of medicinal chemistry, Feb-01, Volume: 187	Synthesis and structure-activity relationship studies of α-naphthoflavone derivatives as CYP1B1 inhibitors.
AID6984	Michaelis-Menten constant for 7-ethoxycoumarin deethylation in rat liver microsomes exposed to beta-naphthoflavone at 27.5 uM	1981	Journal of medicinal chemistry, Jul, Volume: 24, Issue:7	Effects of 1-arylpyrroles and naphthoflavones upon cytochrome P-450 dependent monooxygenase activities.
AID1238335	Inhibition of CYP1A2 (unknown origin) at 4 uM by luminescent readout-based method	2015	Bioorganic & medicinal chemistry letters, Aug-15, Volume: 25, Issue:16	Phenoxymethyl 1,3-oxazoles and 1,2,4-oxadiazoles as potent and selective agonists of free fatty acid receptor 1 (GPR40).
AID1372158	Inhibition of human CYP1A1 transfected in HEK293 cells assessed as cell toxicity
AID1372151	Inhibition of human CYP1A2 expressed in HEK293 cells by fluorescence assay
AID1680588	Antiproliferative activity against human MCF-7 cells overexpressing CYP1A1 assessed as reduction in cell viability
AID1368050	Inhibition of human CYP1B1 expressed in yeast microsomal membranes using 7-ethoxyresorufin as substrate measured after 10 mins by fluorescence assay	2017	Bioorganic & medicinal chemistry letters, 12-15, Volume: 27, Issue:24	(E)-3-(3,4,5-Trimethoxyphenyl)-1-(pyridin-4-yl)prop-2-en-1-one, a heterocyclic chalcone is a potent and selective CYP1A1 inhibitor and cancer chemopreventive agent.
AID1739435	Inhibition of CYP1A2 in human liver microsomes using phenacetin as substrate incubated for 5 mins followed by NADPH addition and measured after 20 mins by LC-MS/MS analysis	2020	European journal of medicinal chemistry, Aug-15, Volume: 200	Substituted benzothiophene and benzofuran derivatives as a novel class of bone morphogenetic Protein-2 upregulators: Synthesis, anti-osteoporosis efficacies in ovariectomized rats and a zebrafish model, and ADME properties.
AID1368059	Inhibition of recombinant human CYP1B1 expressed in HEK293 cells using 7-ethoxyresorufin as substrate pretreated for 30 mins followed by substrate addition measured for 60 mins by fluorescence assay	2017	Bioorganic & medicinal chemistry letters, 12-15, Volume: 27, Issue:24	(E)-3-(3,4,5-Trimethoxyphenyl)-1-(pyridin-4-yl)prop-2-en-1-one, a heterocyclic chalcone is a potent and selective CYP1A1 inhibitor and cancer chemopreventive agent.
AID1310919	Inhibition of recombinant human CYP1A2 by P450-Glo luminescence assay	2016	Journal of medicinal chemistry, 05-26, Volume: 59, Issue:10	2-(3-Methoxyphenyl)quinazoline Derivatives: A New Class of Direct Constitutive Androstane Receptor (CAR) Agonists.
AID1515301	Binding affinity to human C-terminal 4His-tagged CYP1B1 expressed in Escherichia coli DH5alpha assessed as spectral dissociation constant by spectrophotometric analysis	2019	Bioorganic & medicinal chemistry, 01-15, Volume: 27, Issue:2	Design and synthesis of selective CYP1B1 inhibitor via dearomatization of α-naphthoflavone.
AID1368082	Inhibition of recombinant human CYP1B1 expressed in HEK293 cells assessed as potentiation of cisplatin-induced cytotoxicity by measuring reduction in cisplatin EC50 by MTT assay	2017	Bioorganic & medicinal chemistry letters, 12-15, Volume: 27, Issue:24	(E)-3-(3,4,5-Trimethoxyphenyl)-1-(pyridin-4-yl)prop-2-en-1-one, a heterocyclic chalcone is a potent and selective CYP1A1 inhibitor and cancer chemopreventive agent.
AID7017	Maximum rate constant for 7-ethoxycoumarin deethylation in rat liver microsomes exposed to beta-naphthoflavone at concentration of 27.5 uM	1981	Journal of medicinal chemistry, Jul, Volume: 24, Issue:7	Effects of 1-arylpyrroles and naphthoflavones upon cytochrome P-450 dependent monooxygenase activities.
AID1203565	Inhibition of CYP1B1 in TCDD-stimulated human MCF7 cells assessed as inhibition of anticancer drug resistance by measuring docetaxel cytotoxic IC50 at 5 uM after 48 hrs by MTT assay (Rvb = 139.8 +/- 11.5 microM)	2015	Journal of medicinal chemistry, Apr-23, Volume: 58, Issue:8	Design and Synthesis of New α-Naphthoflavones as Cytochrome P450 (CYP) 1B1 Inhibitors To Overcome Docetaxel-Resistance Associated with CYP1B1 Overexpression.
AID1372143	Inhibition of human CYP1B1 expressed in yeast microsomal membranes at 10 uM using 7-ethoxyresorufin as substrate by fluorescence assay relative to control
AID243248	Ratio of maximum concentration bound and specificity sum for triplex nucleic acids	2004	Journal of medicinal chemistry, Nov-04, Volume: 47, Issue:23	Structural selectivity of aromatic diamidines.
AID1441870	Inhibition of human liver CYP1B1 expressed in Saccharomyces cerevisiae YY7 cells using 7-ethoxyresorufin as substrate after 10 mins by fluorescence assay	2017	European journal of medicinal chemistry, Mar-31, Volume: 129	Discovery and characterization of novel CYP1B1 inhibitors based on heterocyclic chalcones: Overcoming cisplatin resistance in CYP1B1-overexpressing lines.
AID1537806	Inhibition of recombinant human CYP1A2 expressed in supersomes using 7-ethoxyresorufin as substrate after 50 mins in presence of NADP+ by EROD assay	2019	MedChemComm, Sep-01, Volume: 10, Issue:9	Development of benzochalcone derivatives as selective CYP1B1 inhibitors and anticancer agents.
AID1411748	Inhibition of human recombinant CYP1A1 expressed in adherent HEK293 cells assessed as protection of cells against CYP1A1-mediated sensitivity to to B[a]P-induced cytotoxicity by measuring B[a]P- EC50 by MTT assay (Rvb = 0.8 +/- 0.1 uM)	2018	MedChemComm, Feb-01, Volume: 9, Issue:2	Identification of karanjin isolated from the Indian beech tree as a potent CYP1 enzyme inhibitor with cellular efficacy
AID1411733	Inhibition of recombinant human CYP1B1 expressed in baker's yeast-derived microsomes (Sacchrosomes) at 10 uM using 7-ethoxyresorufin substrate by EROD assay relative to control	2018	MedChemComm, Feb-01, Volume: 9, Issue:2	Identification of karanjin isolated from the Indian beech tree as a potent CYP1 enzyme inhibitor with cellular efficacy
AID1239148	Inhibition of human microsomal CYP1A1-dependent ethoxyresorufin-O-deethylase activity by spectrofluorimetric analysis in presence of NADPH regenerating solution	2015	Journal of medicinal chemistry, Aug-27, Volume: 58, Issue:16	A Ligand-Based Drug Design. Discovery of 4-Trifluoromethyl-7,8-pyranocoumarin as a Selective Inhibitor of Human Cytochrome P450 1A2.
AID1680584	Induction of cell cycle arrest in human MCF7 over expressing CYP1A cells assessed as accumulation at G2/M phase incubated for 24 hrs by PI staining based flow cytometric analysis (Rvb = 22.6%)
AID1372150	Inhibition of human CYP1B1 expressed in HEK293 cells by fluorescence assay
AID1437047	Inhibition of porcine cholesterol esterase at 1 nM using para-nitrophenyl butyrate as substrate after 5 mins in presence of sodium taurocholate by spectrophotometric method relative to control	2017	Bioorganic & medicinal chemistry letters, 02-15, Volume: 27, Issue:4	Benzoflavones as cholesterol esterase inhibitors: Synthesis, biological evaluation and docking studies.
AID1437052	Inhibition of porcine cholesterol esterase using para-nitrophenyl butyrate as substrate after 5 mins in presence of sodium taurocholate by spectrophotometric method	2017	Bioorganic & medicinal chemistry letters, 02-15, Volume: 27, Issue:4	Benzoflavones as cholesterol esterase inhibitors: Synthesis, biological evaluation and docking studies.
AID1898236	Inhibition of CYP1A2 in human liver microsomes using phenacetin as substrate in presence of NADPH
AID738376	Inhibition of human CYP1A2 at 3 uM	2013	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 23, Issue:7	Synthesis and evaluation of non-dimeric HCV NS5A inhibitors.
AID1822287	Inhibition of CYP1A2 in human liver microsomes using phenacetin as substrate incubated for 15 to 45 mins in presence of NADPH	2022	Journal of medicinal chemistry, 02-10, Volume: 65, Issue:3	Discovery of Novel Pyridine-Dimethyl-Phenyl-DAPY Hybrids by Molecular Fusing of Methyl-Pyrimidine-DAPYs and Difluoro-Pyridinyl-DAPYs: Improving the Druggability toward High Inhibitory Activity, Solubility, Safety, and PK.
AID1537808	Selectivity index, ratio of IC50 for recombinant human CYP1A2 expressed in supersomes to IC50 for recombinant human CYP1B1 expressed in supersomes	2019	MedChemComm, Sep-01, Volume: 10, Issue:9	Development of benzochalcone derivatives as selective CYP1B1 inhibitors and anticancer agents.
AID311074	Inhibition of CYP1A2	2007	Bioorganic & medicinal chemistry, Aug-01, Volume: 15, Issue:15	Targeting cytochrome P450 enzymes: a new approach in anti-cancer drug development.
AID1441862	Solubility of the compound in pH 1.2 simulated gastric fluid	2017	European journal of medicinal chemistry, Mar-31, Volume: 129	Discovery and characterization of novel CYP1B1 inhibitors based on heterocyclic chalcones: Overcoming cisplatin resistance in CYP1B1-overexpressing lines.
AID1527834	Displacement of 2-azido-3-[125I]7,8-dibromodibenzo-pdioxin from C57BL/6J mouse liver AhR incubated for 20 mins by gamma counting based autoradiography	2020	European journal of medicinal chemistry, Jan-01, Volume: 185	Targeting Aryl hydrocarbon receptor for next-generation immunotherapies: Selective modulators (SAhRMs) versus rapidly metabolized ligands (RMAhRLs).
AID1863226	Inhibition of CYP1A2 in human liver microsomes using ethoxyresorufin as substrate and measured by LC-MS/MS analysis	2022	European journal of medicinal chemistry, Oct-05, Volume: 240	4th generation nonsteroidal aromatase inhibitors: An iterative SAR-guided design, synthesis, and biological evaluation towards picomolar dual binding inhibitors.
AID1368051	Inhibition of human CYP1A2 expressed in yeast microsomal membranes using 3-cyano-7-ethoxycoumarin as substrate measured after 10 mins by fluorescence assay	2017	Bioorganic & medicinal chemistry letters, 12-15, Volume: 27, Issue:24	(E)-3-(3,4,5-Trimethoxyphenyl)-1-(pyridin-4-yl)prop-2-en-1-one, a heterocyclic chalcone is a potent and selective CYP1A1 inhibitor and cancer chemopreventive agent.
AID1727623	Selectivity index, ratio of IC50 for recombinant human CYP1A1 to IC50 for recombinant human CYP1B1	2021	European journal of medicinal chemistry, Jan-01, Volume: 209	Discovery of heterocycle-containing α-naphthoflavone derivatives as water-soluble, highly potent and selective CYP1B1 inhibitors.
AID53739	Binding affinity was measured on Cytochrome P450 19A1	1990	Journal of medicinal chemistry, Nov, Volume: 33, Issue:11	Mechanism and inhibition of cytochrome P-450 aromatase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	160 (25.08)	18.7374
1990's	162 (25.39)	18.2507
2000's	160 (25.08)	29.6817
2010's	119 (18.65)	24.3611
2020's	37 (5.80)	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	1 (0.15%)	5.53%
Reviews	10 (1.50%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	654 (98.35%)	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
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	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
4-hydroxybenzoic acid 4-hydroxybenzoic acid : A monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring.	3.1	1	0	monohydroxybenzoic acid	algal 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.	1.97	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
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	1.97	1	0	ketone body; methyl ketone; propanones; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; human metabolite; polar aprotic solvent
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.	2	1	0	acridines; aromatic ether; organochlorine compound; tertiary amino compound	antimalarial; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor
benzene [no description available]	1.96	1	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.	3.1	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
benzyl alcohol Benzyl Alcohol: A colorless liquid with a sharp burning taste and slight odor. It is used as a local anesthetic and to reduce pain associated with LIDOCAINE injection. Also, it is used in the manufacture of other benzyl compounds, as a pharmaceutic aid, and in perfumery and flavoring.. hydroxytoluene : Any member of the class of toluenes carrying one or more hydroxy substituents.. benzyl alcohol : An aromatic alcohol that consists of benzene bearing a single hydroxymethyl substituent.. aromatic alcohol : Any alcohol in which the alcoholic hydroxy group is attached to a carbon which is itself bonded to an aromatic ring.. aromatic primary alcohol : Any primary alcohol in which the alcoholic hydroxy group is attached to a carbon which is itself bonded to an aromatic ring.	3.1	1	0	benzyl alcohols	antioxidant; fragrance; metabolite; solvent
butyric acid Butyric Acid: A four carbon acid, CH3CH2CH2COOH, with an unpleasant odor that occurs in butter and animal fat as the glycerol ester.. butyrate : A short-chain fatty acid anion that is the conjugate base of butyric acid, obtained by deprotonation of the carboxy group.. butyric acid : A straight-chain saturated fatty acid that is butane in which one of the terminal methyl groups has been oxidised to a carboxy group.	3.1	1	0	fatty acid 4:0; straight-chain saturated fatty acid	human urinary metabolite; Mycoplasma genitalium metabolite
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.	3.77	11	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
chlordecone [no description available]	1.97	1	0	cyclic ketone; organochlorine compound	insecticide; persistent organic pollutant
chlorine chloride : A halide anion formed when chlorine picks up an electron to form an an anion.	2.01	1	0	halide anion; monoatomic chlorine	cofactor; Escherichia coli metabolite; human metabolite
coumarin 2H-chromen-2-one: coumarin derivative	3.26	6	0	coumarins	fluorescent dye; human metabolite; plant 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).	3.1	1	0	monohydroxybenzoic acid	algal metabolite; antifungal agent; antiinfective agent; EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor; keratolytic drug; plant hormone; plant metabolite
gallic acid gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.	3.5	2	0	trihydroxybenzoic acid	antineoplastic agent; antioxidant; apoptosis inducer; astringent; cyclooxygenase 2 inhibitor; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; geroprotector; human xenobiotic metabolite; plant metabolite
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.	3.1	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	antibacterial agent; Escherichia coli metabolite; human metabolite
4-aminophenol 4-aminophenol: RN given refers to parent cpd. 4-aminophenol : An amino phenol (one of the three possible isomers) which has the single amino substituent located para to the phenolic -OH group.	3.1	1	0	aminophenol	allergen; metabolite
bupropion Bupropion: A propiophenone-derived antidepressant and antismoking agent that inhibits the uptake of DOPAMINE.. bupropion : An aromatic ketone that is propiophenone carrying a tert-butylamino group at position 2 and a chloro substituent at position 3 on the phenyl ring.	2.06	1	0	aromatic ketone; monochlorobenzenes; secondary amino compound	antidepressant; environmental contaminant; xenobiotic
taxifolin [no description available]	1.99	1	0	3'-hydroxyflavanones; 4'-hydroxyflavanones; dihydroflavonols; pentahydroxyflavanone; secondary alpha-hydroxy ketone
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.	2.07	1	0	dibenzofurans; mancude organic heterotricyclic parent; polycyclic heteroarene	xenobiotic
dimethyl sulfoxide Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.	2.68	3	0	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
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.	7.05	1	0	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
hydroquinone [no description available]	3.5	2	0	benzenediol; hydroquinones	antioxidant; carcinogenic agent; cofactor; Escherichia coli metabolite; human xenobiotic metabolite; mouse metabolite; skin lightening agent
imidazole imidazole: RN given refers to parent cpd. 1H-imidazole : An imidazole tautomer which has the migrating hydrogen at position 1.	2.41	2	0	imidazole
kynurenine Kynurenine: A metabolite of the essential amino acid tryptophan metabolized via the tryptophan-kynurenine pathway.. kynurenine : A ketone that is alanine in which one of the methyl hydrogens is substituted by a 2-aminobenzoyl group.	2.13	1	0	aromatic ketone; non-proteinogenic alpha-amino acid; substituted aniline	human metabolite
thioctic acid Thioctic Acid: An octanoic acid bridged with two sulfurs so that it is sometimes also called a pentanoic acid in some naming schemes. It is biosynthesized by cleavage of LINOLEIC ACID and is a coenzyme of oxoglutarate dehydrogenase (KETOGLUTARATE DEHYDROGENASE COMPLEX). It is used in DIETARY SUPPLEMENTS.	2.05	1	0	dithiolanes; heterocyclic fatty acid; thia fatty acid	fundamental metabolite; geroprotector
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.	3.52	2	0	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
melatonin [no description available]	3.55	2	0	acetamides; tryptamines	anticonvulsant; central nervous system depressant; geroprotector; hormone; human metabolite; immunological adjuvant; mouse metabolite; radical scavenger
naphthalene [no description available]	1.96	1	0	naphthalenes; ortho-fused bicyclic arene	apoptosis inhibitor; carcinogenic agent; environmental contaminant; mouse metabolite; plant metabolite; volatile oil component
niacinamide nicotinamide : A pyridinecarboxamide that is pyridine in which the hydrogen at position 3 is replaced by a carboxamide group.	1.96	1	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
nitrites Nitrites: Salts of nitrous acid or compounds containing the group NO2-. The inorganic nitrites of the type MNO2 (where M=metal) are all insoluble, except the alkali nitrites. The organic nitrites may be isomeric, but not identical with the corresponding nitro compounds. (Grant & Hackh's Chemical Dictionary, 5th ed)	2.03	1	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.	3.1	1	0	dimethylaniline; tertiary amine
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.	3.56	2	0	4-nitrophenols	human xenobiotic metabolite; mouse metabolite
parathion [no description available]	3.51	2	0	C-nitro compound; organic thiophosphate; organothiophosphate insecticide	acaricide; agrochemical; avicide; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; mouse metabolite
pentachlorophenol PENTA: structure given in first source	2.9	4	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.'	2.02	1	0	ortho-fused polycyclic arene; ortho-fused tricyclic hydrocarbon; phenanthrenes	environmental contaminant; mouse metabolite
phenol [no description available]	3.1	1	0	phenols	antiseptic drug; disinfectant; human xenobiotic metabolite; mouse metabolite
pyrazinamide pyrazinecarboxamide : A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of pyrazinoic acid (pyrazine-2-carboxylic acid) with ammonia. A prodrug for pyrazinoic acid, pyrazinecarboxamide is used as part of multidrug regimens for the treatment of tuberculosis.	2.03	1	0	monocarboxylic acid amide; N-acylammonia; pyrazines	antitubercular agent; prodrug
pyrazole 1H-pyrazole : The 1H-tautomer of pyrazole.	2.37	2	0	pyrazole
pyridine azine : An organonitrogen compound of general structure RCH=N-N=CHR or RR'C=N-N=CRR'.	1.96	1	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.	3.51	2	0	benzenetriol; phenolic donor	plant metabolite
toluene methylbenzene : Any alkylbenzene that is benzene substituted with one or more methyl groups.	2.08	1	0	methylbenzene; toluenes; volatile organic compound	cholinergic antagonist; fuel additive; neurotoxin; non-polar solvent
tryptophan [no description available]	3.1	1	0	alpha-amino acid; amino acid zwitterion; aminoalkylindole; aromatic amino acid; polar amino acid	Daphnia magna metabolite
uroporphyrinogen iii Uroporphyrinogens: Porphyrinogens which are intermediates in heme biosynthesis. They have four acetic acid and four propionic acid side chains attached to the pyrrole rings. Uroporphyrinogen I and III are formed from polypyrryl methane in the presence of uroporphyrinogen III cosynthetase and uroporphyrin I synthetase, respectively. They can yield uroporphyrins by autooxidation or coproporphyrinogens by decarboxylation.	1.97	1	0	uroporphyrinogen	Escherichia coli metabolite; mouse metabolite
vanillin Vanilla: A plant genus of the family ORCHIDACEAE that is the source of the familiar flavoring used in foods and medicines (FLAVORING AGENTS).	3.1	1	0	benzaldehydes; monomethoxybenzene; phenols	anti-inflammatory agent; anticonvulsant; antioxidant; flavouring agent; plant metabolite
catechin [no description available]	3.1	1	0	hydroxyflavan
menthol Menthol: A monoterpene cyclohexanol produced from mint oils.	3.1	1	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	2.03	1	0	phenanthroline	EC 2.7.1.1 (hexokinase) inhibitor; EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor
1-aminobenzotriazole [no description available]	2.72	3	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.	2.11	1	0	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
14,15-epoxy-5,8,11-eicosatrienoic acid 14,15-epoxy-5,8,11-eicosatrienoic acid: RN given refers to cpd without isomeric designation	1.97	1	0	long-chain fatty acid
17-octadecynoic acid octadec-17-ynoic acid : An acetylenic fatty acid that is octadecanoi acid (stearic acid) which has been doubly dehydrogenated at positions 17 and 18 to give the corresponding alkynoic acid.	2.03	1	0	acetylenic fatty acid; long-chain fatty acid; monounsaturated fatty acid; terminal acetylenic compound	EC 1.14.14.94 (leukotriene-B4 20-monooxygenase) inhibitor; EC 1.14.15.3 (alkane 1-monooxygenase) inhibitor; P450 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.	2	1	0	chlorophenoxyacetic acid; dichlorobenzene	agrochemical; defoliant; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; environmental contaminant; phenoxy herbicide; synthetic auxin
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.	3.08	5	0	imidazopyridine; primary amino compound	carcinogenic agent; mutagen
2-aminofluorene [no description available]	4.46	7	0
2-aminoethoxydiphenyl borate 2-aminoethoxydiphenyl borate: is a novel membrane-penetrable modulator and transient receptor potential channel blocker; structure in first source; do not confuse with 2-APB cpd. 2-aminoethoxydiphenylborane : An organoboron compound that is diphenylborane in which the borane hydrogen is replaced by a 2-aminoethoxy group.	2.04	1	0	organoboron compound; primary amino compound	calcium channel blocker; IP3 receptor antagonist; potassium channel opener
n-methyl-3,4-methylenedioxyamphetamine N-Methyl-3,4-methylenedioxyamphetamine: An N-substituted amphetamine analog. It is a widely abused drug classified as a hallucinogen and causes marked, long-lasting changes in brain serotonergic systems. It is commonly referred to as MDMA or ecstasy.. 3,4-methylenedioxymethamphetamine : A member of the class of benzodioxoles that is 1,3-benzodioxole substituted by a 2-(methylamino)propyl group at position 5.	3.53	2	0	amphetamines; benzodioxoles	neurotoxin
amitrole Amitrole: A non-selective post-emergence, translocated herbicide. According to the Seventh Annual Report on Carcinogens (PB95-109781, 1994) this substance may reasonably be anticipated to be a carcinogen. (From Merck Index, 12th ed) It is an irreversible inhibitor of CATALASE, and thus impairs activity of peroxisomes.. amitrole : A member of the class of triazoles that is 1H-1,2,4-triazole substituted by an amino group at position 3. Used to control annual grasses and aquatic weeds (but not on food crops because it causes cancer in laboratory animals). Its use within the EU was banned from September 2017 on the grounds of potential groundwater contamination and risks to aquatic life; there have also been concerns about its endocrine-disrupting properties.	2	1	0	aromatic amine; triazoles	carotenoid biosynthesis inhibitor; EC 1.11.1.6 (catalase) inhibitor; herbicide
3-aminobenzamide [no description available]	2.03	1	0	benzamides; substituted aniline	EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor
3-methoxymorphinan 3-methoxymorphinan: dextromethorphan metabolite; RN & N1 from 9th CI Form Index; RN given refers to cpd without isomeric designation; structure in first source	1.99	1	0
3-methylcholanthrene Methylcholanthrene: A carcinogen that is often used in experimental cancer studies.. 3-methylcholanthrene : A pentacyclic ortho- and peri-fused polycyclic arene consisting of a dihydrocyclopenta[ij]tetraphene ring system with a methyl substituent at the 3-position.	5.44	63	0	ortho- and peri-fused polycyclic arene	aryl hydrocarbon receptor agonist; carcinogenic agent
pleconaril WIN 63843: structure given in first source	2.41	1	0
homovanillic acid Homovanillic Acid: A 3-O-methyl ETHER of (3,4-dihydroxyphenyl)acetic acid.. homovanillate : A hydroxy monocarboxylic acid anion which is obtained by deprotonation of the carboxy group of homovanillic acid.. homovanillic acid : A monocarboxylic acid that is the 3-O-methyl ether of (3,4-dihydroxyphenyl)acetic acid. It is a catecholamine metabolite.	3.1	1	0	guaiacols; monocarboxylic acid	human metabolite; mouse metabolite
5,8,11,14-eicosatetraynoic acid 5,8,11,14-Eicosatetraynoic Acid: A 20-carbon unsaturated fatty acid containing 4 alkyne bonds. It inhibits the enzymatic conversion of arachidonic acid to prostaglandins E(2) and F(2a).	1.99	1	0	long-chain fatty acid
6-hydroxymelatonin 6-hydroxymelatonin : A member of the class of tryptamines that is melatonin with a hydroxy group substituent at position 6.	3.1	1	0	acetamides; tryptamines	metabolite; mouse metabolite
7-hydroxyflavanone 7-hydroxyflavanone: structure given in first source. 7-hydroxyflavanone : A monohydroxyflavanone that is flavanone substituted by a hydroxy group at position 7.	2.04	1	0	monohydroxyflavanone
oxyquinoline Oxyquinoline: An antiseptic with mild fungistatic, bacteriostatic, anthelmintic, and amebicidal action. It is also used as a reagent and metal chelator, as a carrier for radio-indium for diagnostic purposes, and its halogenated derivatives are used in addition as topical anti-infective agents and oral antiamebics.. quinolin-8-ol : A monohydroxyquinoline that is quinoline substituted by a hydroxy group at position 8. Its fungicidal properties are used for the control of grey mould on vines and tomatoes.	3.1	1	0	monohydroxyquinoline	antibacterial agent; antifungal agrochemical; antiseptic drug; iron chelator
tacrine Tacrine: A cholinesterase inhibitor that crosses the blood-brain barrier. Tacrine has been used to counter the effects of muscle relaxants, as a respiratory stimulant, and in the treatment of Alzheimer's disease and other central nervous system disorders.. tacrine : A member of the class of acridines that is 1,2,3,4-tetrahydroacridine substituted by an amino group at position 9. It is used in the treatment of Alzheimer's disease.	3.57	2	0	acridines; aromatic amine	EC 3.1.1.7 (acetylcholinesterase) inhibitor
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.	4.19	5	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
alprazolam Alprazolam: A triazolobenzodiazepine compound with antianxiety and sedative-hypnotic actions, that is efficacious in the treatment of PANIC DISORDERS, with or without AGORAPHOBIA, and in generalized ANXIETY DISORDERS. (From AMA Drug Evaluations Annual, 1994, p238). alprazolam : A member of the class of triazolobenzodiazepines that is 4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine carrying methyl, phenyl and chloro substituents at positions 1, 6 and 8 respectively. Alprazolam is only found in individuals that have taken this drug.	2	1	0	organochlorine compound; triazolobenzodiazepine	anticonvulsant; anxiolytic drug; GABA agonist; muscle relaxant; sedative; xenobiotic
aminoglutethimide Aminoglutethimide: An aromatase inhibitor that is used in the treatment of advanced BREAST CANCER.. aminoglutethimide : A dicarboximide that is a six-membered cyclic compound having ethyl and 4-aminophenyl substituents at the 3-position.	4	4	0	dicarboximide; piperidones; substituted aniline	adrenergic agent; anticonvulsant; antineoplastic agent; EC 1.14.14.14 (aromatase) inhibitor
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
theophylline [no description available]	3.79	11	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.	3.83	3	0	1-benzofurans; aromatic ketone; organoiodine compound; tertiary amino compound	cardiovascular drug
amitriptyline Amitriptyline: Tricyclic antidepressant with anticholinergic and sedative properties. It appears to prevent the re-uptake of norepinephrine and serotonin at nerve terminals, thus potentiating the action of these neurotransmitters. Amitriptyline also appears to antagonize cholinergic and alpha-1 adrenergic responses to bioactive amines.. amitriptyline : An organic tricyclic compound that is 10,11-dihydro-5H-dibenzo[a,d][7]annulene substituted by a 3-(dimethylamino)propylidene group at position 5.	4.27	5	0	carbotricyclic compound; tertiary amine	adrenergic uptake inhibitor; antidepressant; environmental contaminant; tropomyosin-related kinase B receptor agonist; xenobiotic
amodiaquine Amodiaquine: A 4-aminoquinoline compound with anti-inflammatory properties.. amodiaquine : A quinoline having a chloro group at the 7-position and an aryl amino group at the 4-position.	2.03	1	0	aminoquinoline; organochlorine compound; phenols; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; drug allergen; EC 2.1.1.8 (histamine N-methyltransferase) inhibitor; non-steroidal anti-inflammatory drug; prodrug
anastrozole [no description available]	2.05	1	0	nitrile; triazoles	antineoplastic agent; EC 1.14.14.14 (aromatase) inhibitor
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.	2.37	2	0	pyrazolone	antipyretic; cyclooxygenase 3 inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
aspirin Aspirin: The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5). acetylsalicylate : A benzoate that is the conjugate base of acetylsalicylic acid, arising from deprotonation of the carboxy group.. acetylsalicylic acid : A member of the class of benzoic acids that is salicylic acid in which the hydrogen that is attached to the phenolic hydroxy group has been replaced by an acetoxy group. A non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity.	4.01	4	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.	2.1	1	0	benzimidazoles; piperidines	anti-allergic agent; anticoronaviral agent; H1-receptor antagonist
atenolol Atenolol: A cardioselective beta-1 adrenergic blocker possessing properties and potency similar to PROPRANOLOL, but without a negative inotropic effect.. atenolol : An ethanolamine compound having a (4-carbamoylmethylphenoxy)methyl group at the 1-position and an N-isopropyl substituent.	2.17	1	0	ethanolamines; monocarboxylic acid amide; propanolamine	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; environmental contaminant; sympatholytic agent; xenobiotic
benzamide benzamide : An aromatic amide that consists of benzene bearing a single carboxamido substituent. The parent of the class of benzamides.	2.03	1	0	benzamides
benzbromarone Benzbromarone: Uricosuric that acts by increasing uric acid clearance. It is used in the treatment of gout.. benzbromarone : 1-Benzofuran substituted at C-2 and C-3 by an ethyl group and a 3,5-dibromo-4-hydroxybenzoyl group respectively. An inhibitor of CYP2C9, it is used as an anti-gout medication.	2.72	2	0	1-benzofurans; aromatic ketone	uricosuric drug
benzo(a)pyrene Benzo(a)pyrene: A potent mutagen and carcinogen. It is a public health concern because of its possible effects on industrial workers, as an environmental pollutant, an as a component of tobacco smoke.. benzo[a]pyrene : An ortho- and peri-fused polycyclic arene consisting of five fused benzene rings.	6.61	67	0	ortho- and peri-fused polycyclic arene	carcinogenic agent; mouse metabolite
benzyl isothiocyanate benzyl isothiocyanate: inhibits carcinogen-induced neoplasia; structure in Negwer, 5th ed, #715; also promotes urinary bladder carcinoma	3.12	1	0	benzenes; isothiocyanate	antibacterial drug
berberine [no description available]	3.63	2	0	alkaloid antibiotic; berberine alkaloid; botanical anti-fungal agent; organic heteropentacyclic compound	antilipemic drug; antineoplastic agent; antioxidant; EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor; EC 1.21.3.3 (reticuline oxidase) inhibitor; EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor; EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor; EC 2.7.11.10 (IkappaB kinase) inhibitor; EC 3.1.1.4 (phospholipase A2) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; geroprotector; hypoglycemic agent; metabolite; potassium channel blocker
5-methoxypsoralen 5-Methoxypsoralen: A linear furanocoumarin that has phototoxic and anti-inflammatory properties, with effects similar to METHOXSALEN. It is used in PUVA THERAPY for the treatment of PSORIASIS.. 5-methoxypsoralen : A 5-methoxyfurocoumarin that is psoralen substituted by a methoxy group at position 5.	3.57	2	0	5-methoxyfurocoumarin; organic heterotricyclic compound; psoralens	hepatoprotective agent; plant metabolite
beta-naphthoflavone beta-Naphthoflavone: A polyaromatic hydrocarbon inducer of P4501A1 and P4501A2 cytochromes. (Proc Soc Exp Biol Med 1994 Dec:207(3):302-308). beta-naphthoflavone : An extended flavonoid resulting from the formal fusion of a benzene ring with the f side of flavone.	7.42	90	0	extended flavonoid; naphtho-gamma-pyrone; organic heterotricyclic compound	aryl hydrocarbon receptor agonist
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.	2.01	1	0	(trifluoromethyl)benzenes; monocarboxylic acid amide; monofluorobenzenes; nitrile; sulfone; tertiary alcohol
bumetanide [no description available]	3.1	1	0	amino acid; benzoic acids; sulfonamide	diuretic; EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor
caffeine [no description available]	4.99	9	1	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.	4.4	6	0	aromatic ether; nitrile; polyether; tertiary amino compound
cannabinol Cannabinol: A physiologically inactive constituent of Cannabis sativa L.	3.25	1	0	dibenzopyran
carbamazepine Carbamazepine: A dibenzazepine that acts as a sodium channel blocker. It is used as an anticonvulsant for the treatment of grand mal and psychomotor or focal SEIZURES. It may also be used in the management of BIPOLAR DISORDER, and has analgesic properties.. carbamazepine : A dibenzoazepine that is 5H-dibenzo[b,f]azepine carrying a carbamoyl substituent at the azepine nitrogen, used as an anticonvulsant.	4.01	4	0	dibenzoazepine; ureas	analgesic; anticonvulsant; antimanic drug; drug allergen; EC 3.5.1.98 (histone deacetylase) inhibitor; environmental contaminant; glutamate transporter activator; mitogen; non-narcotic analgesic; sodium channel blocker; xenobiotic
carbamazepine epoxide carbamazepine epoxide: metabolite of carbamazepine; RN given refers to unlabeled cpd. carbamazepine-10,11-epoxide : An epoxide and metabolite of carbamazepine.	2.4	2	0	dibenzoazepine; epoxide; ureas	allergen; drug metabolite; marine xenobiotic metabolite
carbofuran Carbofuran: A cholinesterase inhibitor that is used as a systemic insecticide, an acaricide, and nematocide. (From Merck Index, 11th ed)	2	1	0	1-benzofurans; carbamate ester	acaricide; agrochemical; avicide; carbamate insecticide; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; nematicide
chlorpheniramine Chlorpheniramine: A histamine H1 antagonist used in allergic reactions, hay fever, rhinitis, urticaria, and asthma. It has also been used in veterinary applications. One of the most widely used of the classical antihistaminics, it generally causes less drowsiness and sedation than PROMETHAZINE.. chlorphenamine : A tertiary amino compound that is propylamine which is substituted at position 3 by a pyridin-2-yl group and a p-chlorophenyl group and in which the hydrogens attached to the nitrogen are replaced by methyl groups. A histamine H1 antagonist, it is used to relieve the symptoms of hay fever, rhinitis, urticaria, and asthma.	3.1	1	0	monochlorobenzenes; pyridines; tertiary amino compound	anti-allergic agent; antidepressant; antipruritic drug; H1-receptor antagonist; histamine antagonist; serotonin uptake inhibitor
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.	3.1	1	0	organochlorine compound; phenothiazines; tertiary amine	anticoronaviral agent; antiemetic; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; phenothiazine antipsychotic drug
chlorzoxazone Chlorzoxazone: A centrally acting central muscle relaxant with sedative properties. It is claimed to inhibit muscle spasm by exerting an effect primarily at the level of the spinal cord and subcortical areas of the brain. (From Martindale, The Extra Pharmacopoea, 30th ed, p1202). chlorzoxazone : A member of the class of 1,3-benzoxazoles that is 1,3-benzoxazol-2-ol in which the hydrogen atom at position 5 is substituted by chlorine. A centrally acting muscle relaxant with sedative properties, it is used for the symptomatic treatment of painful muscle spasm.	2.92	4	0	1,3-benzoxazoles; heteroaryl hydroxy compound; organochlorine compound	muscle relaxant; sedative
6-hydroxychlorzoxazone 6-hydroxychlorzoxazone: chlorzoxazone metabolite in humans	1.99	1	0	benzoxazole
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.	4.34	6	0	aliphatic sulfide; guanidines; imidazoles; nitrile	adjuvant; analgesic; anti-ulcer drug; H2-receptor antagonist; P450 inhibitor
ciprofibrate [no description available]	3.1	1	0	cyclopropanes; monocarboxylic acid; organochlorine compound	antilipemic drug
clofibrate angiokapsul: contains clofibrate & insoitolnicotinate	3.49	2	0	aromatic ether; ethyl ester; monochlorobenzenes	anticholesteremic drug; antilipemic drug; geroprotector; PPARalpha agonist
clofibric acid Clofibric Acid: An antilipemic agent that is the biologically active metabolite of CLOFIBRATE.. clofibric acid : A monocarboxylic acid that is isobutyric acid substituted at position 2 by a p-chlorophenoxy group. It is a metabolite of the drug clofibrate.	3.1	1	0	aromatic ether; monocarboxylic acid; monochlorobenzenes	anticholesteremic drug; antilipemic drug; antineoplastic agent; herbicide; marine xenobiotic metabolite; PPARalpha agonist
clonidine Clonidine: An imidazoline sympatholytic agent that stimulates ALPHA-2 ADRENERGIC RECEPTORS and central IMIDAZOLINE RECEPTORS. It is commonly used in the management of HYPERTENSION.. clonidine (amino form) : A clonidine that is 4,5-dihydro-1H-imidazol-2-amine in which one of the amino hydrogens is replaced by a 2,6-dichlorophenyl group.	2.13	1	0	clonidine; imidazoline
4-chloro-N-(2,6-dimethyl-1-piperidinyl)-3-sulfamoylbenzamide [no description available]	3.1	1	0	sulfonamide
clotrimazole [no description available]	3.38	7	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.	3.1	1	0	cresol	Escherichia coli metabolite; human metabolite; uremic toxin
cyproheptadine Cyproheptadine: A serotonin antagonist and a histamine H1 blocker used as antipruritic, appetite stimulant, antiallergic, and for the post-gastrectomy dumping syndrome, etc.. cyproheptadine : The product resulting from the formal oxidative coupling of position 5 of 5H-dibenzo[a,d]cycloheptene with position 4 of 1-methylpiperidine resulting in the formation of a double bond between the two fragments. It is a sedating antihistamine with antimuscarinic and calcium-channel blocking actions. It is used (particularly as the hydrochloride sesquihydrate) for the relief of allergic conditions including rhinitis, conjunctivitis due to inhalant allergens and foods, urticaria and angioedema, and in pruritic skin disorders. Unlike other antihistamines, it is also a seratonin receptor antagonist, making it useful in conditions such as vascular headache and anorexia.	3.1	1	0	piperidines; tertiary amine	anti-allergic agent; antipruritic drug; gastrointestinal drug; H1-receptor antagonist; serotonergic antagonist
danthron danthron: structure. chrysazin : A dihydroxyanthraquinone that is anthracene-9,10-dione substituted by hydroxy groups at positions 1 and 8.	3.1	1	0	dihydroxyanthraquinone	apoptosis inducer; plant metabolite
dapsone [no description available]	3.1	1	0	substituted aniline; sulfone	anti-inflammatory drug; antiinfective agent; antimalarial; leprostatic drug
debrisoquin Debrisoquin: An adrenergic neuron-blocking drug similar in effects to GUANETHIDINE. It is also noteworthy in being a substrate for a polymorphic cytochrome P-450 enzyme. Persons with certain isoforms of this enzyme are unable to properly metabolize this and many other clinically important drugs. They are commonly referred to as having a debrisoquin 4-hydroxylase polymorphism.	1.97	1	0	carboxamidine; isoquinolines	adrenergic agent; antihypertensive agent; human metabolite; sympatholytic agent
decanoic acid decanoate : A fatty acid anion 10:0 that is the conjugate base of decanoic acid.. decanoic acid : A C10, straight-chain saturated fatty acid.	3.1	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; anti-inflammatory agent; antibacterial agent; human metabolite; plant metabolite; volatile oil component
deferoxamine Deferoxamine: Natural product isolated from Streptomyces pilosus. It forms iron complexes and is used as a chelating agent, particularly in the mesylate form.. desferrioxamine B : An acyclic desferrioxamine that is butanedioic acid in which one of the carboxy groups undergoes formal condensation with the primary amino group of N-(5-aminopentyl)-N-hydroxyacetamide and the second carboxy group undergoes formal condensation with the hydroxyamino group of N(1)-(5-aminopentyl)-N(1)-hydroxy-N(4)-[5-(hydroxyamino)pentyl]butanediamide. It is a siderophore native to Streptomyces pilosus biosynthesised by the DesABCD enzyme cluster as a high affinity Fe(III) chelator.	1.97	1	0	acyclic desferrioxamine	bacterial metabolite; ferroptosis inhibitor; iron chelator; siderophore
desipramine Desipramine: A tricyclic dibenzazepine compound that potentiates neurotransmission. Desipramine selectively blocks reuptake of norepinephrine from the neural synapse, and also appears to impair serotonin transport. This compound also possesses minor anticholinergic activity, through its affinity to muscarinic receptors.. desipramine : A dibenzoazepine consisting of 10,11-dihydro-5H-dibenzo[b,f]azepine substituted on nitrogen with a 3-(methylamino)propyl group.	4.3	3	0	dibenzoazepine; secondary amino compound	adrenergic uptake inhibitor; alpha-adrenergic antagonist; antidepressant; cholinergic antagonist; drug allergen; EC 3.1.4.12 (sphingomyelin phosphodiesterase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; H1-receptor antagonist; serotonin uptake inhibitor
nordazepam Nordazepam: An intermediate in the metabolism of DIAZEPAM to OXAZEPAM. It may have actions similar to those of diazepam.. nordazepam : A 1,4-benzodiazepinone having phenyl and chloro substituents at positions 5 and 7 respectively; it has anticonvulsant, anxiolytic, muscle relaxant and sedative properties but is used primarily in the treatment of anxiety.	1.98	1	0	1,4-benzodiazepinone; organochlorine compound	anticonvulsant; anxiolytic drug; GABA modulator; human metabolite; sedative
eflornithine Eflornithine: An inhibitor of ORNITHINE DECARBOXYLASE, the rate limiting enzyme of the polyamine biosynthetic pathway.. eflornithine : A fluoroamino acid that is ornithine substituted by a difluoromethyl group at position 2.	2	1	0	alpha-amino acid; fluoroamino acid	trypanocidal drug
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.	2.69	3	0	1,4-benzodiazepinone; organochlorine compound	anticonvulsant; anxiolytic drug; environmental contaminant; sedative; xenobiotic
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.	4.44	6	0	amino acid; aromatic amine; dichlorobenzene; monocarboxylic acid; secondary amino compound	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
ddt 1,1-bis(p-chlorophenyl)-2,2,2-trichloroethane: structure in first source	2.1	1	0	benzenoid aromatic compound; chlorophenylethane; monochlorobenzenes; organochlorine insecticide	bridged diphenyl acaricide; carcinogenic agent; endocrine disruptor; persistent organic pollutant
diflunisal Diflunisal: A salicylate derivative and anti-inflammatory analgesic with actions and side effects similar to those of ASPIRIN.. diflunisal : An organofluorine compound comprising salicylic acid having a 2,4-difluorophenyl group at the 5-position.	3.1	1	0	monohydroxybenzoic acid; organofluorine compound	non-narcotic analgesic; non-steroidal anti-inflammatory drug
3,3'-diindolylmethane 3,3'-diindolylmethane: anti-inflammatory from edible cruciferous vegetables; a cytochrome P-450 antagonist	3.59	2	0	indoles	antineoplastic agent; P450 inhibitor
diphenhydramine Diphenhydramine: A histamine H1 antagonist used as an antiemetic, antitussive, for dermatoses and pruritus, for hypersensitivity reactions, as a hypnotic, an antiparkinson, and as an ingredient in common cold preparations. It has some undesired antimuscarinic and sedative effects.. diphenhydramine : An ether that is the benzhydryl ether of 2-(dimethylamino)ethanol. It is a H1-receptor antagonist used as a antipruritic and antitussive drug.. antitussive : An agent that suppresses cough. Antitussives have a central or a peripheral action on the cough reflex, or a combination of both. Compare with expectorants, which are considered to increase the volume of secretions in the respiratory tract, so facilitating their removal by ciliary action and coughing, and mucolytics, which decrease the viscosity of mucus, facilitating its removal by ciliary action and expectoration.	3.1	1	0	ether; tertiary amino compound	anti-allergic agent; antidyskinesia agent; antiemetic; antiparkinson drug; antipruritic drug; antitussive; H1-receptor antagonist; local anaesthetic; muscarinic antagonist; oneirogen; sedative
disulfiram [no description available]	3.55	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
valproic acid Valproic Acid: A fatty acid with anticonvulsant and anti-manic properties that is used in the treatment of EPILEPSY and BIPOLAR DISORDER. The mechanisms of its therapeutic actions are not well understood. It may act by increasing GAMMA-AMINOBUTYRIC ACID levels in the brain or by altering the properties of VOLTAGE-GATED SODIUM CHANNELS.. valproic acid : A branched-chain saturated fatty acid that comprises of a propyl substituent on a pentanoic acid stem.	4.3	3	0	branched-chain fatty acid; branched-chain saturated fatty acid	anticonvulsant; antimanic drug; EC 3.5.1.98 (histone deacetylase) inhibitor; GABA agent; neuroprotective agent; psychotropic drug; teratogenic agent
doxepin Doxepin: A dibenzoxepin tricyclic compound. It displays a range of pharmacological actions including maintaining adrenergic innervation. Its mechanism of action is not fully understood, but it appears to block reuptake of monoaminergic neurotransmitters into presynaptic terminals. It also possesses anticholinergic activity and modulates antagonism of histamine H(1)- and H(2)-receptors.. doxepin : A dibenzooxepine that is 6,11-dihydrodibenzo[b,e]oxepine substituted by a 3-(dimethylamino)propylidene group at position 11. It is used as an antidepressant drug.	3.1	1	0	dibenzooxepine; tertiary amino compound	antidepressant
doxylamine Doxylamine: Histamine H1 antagonist with pronounced sedative properties. It is used in allergies and as an antitussive, antiemetic, and hypnotic. Doxylamine has also been administered in veterinary applications and was formerly used in PARKINSONISM.	3.1	1	0	pyridines; tertiary amine	anti-allergic agent; antiemetic; antitussive; cholinergic antagonist; H1-receptor antagonist; histamine antagonist; sedative
e 4031 E 4031: class III anti-arrhythmia agent; structure given in UD	2.61	2	0	sulfonamide
ebastine [no description available]	2.03	1	0	organic molecular entity
econazole Econazole: An imidazole derivative that is commonly used as a topical antifungal agent.. econazole : A racemate composed of equimolar amounts of (R)- and (S)-econazole. Used (as its nitrate salt) to treat skin infections such as athlete's foot, jock itch, ringworm and other fungal skin infections.. 1-{2-(4-chlorobenzyloxy)-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 4-chlorobenzyl group.	2.39	2	0	dichlorobenzene; ether; imidazoles; monochlorobenzenes
ellipticine ellipticine : A organic heterotetracyclic compound that is pyrido[4,3-b]carbazole carrying two methyl substituents at positions 5 and 11.	3.12	5	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.	4.06	2	0	trihydroxyanthraquinone	antineoplastic agent; laxative; plant metabolite; tyrosine kinase inhibitor
erythrosine Fluoresceins: A family of spiro(isobenzofuran-1(3H),9'-(9H)xanthen)-3-one derivatives. These are used as dyes, as indicators for various metals, and as fluorescent labels in immunoassays.	2.4	2	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.	3.1	1	0	aromatic ether; aromatic ketone; dichlorobenzene; monocarboxylic acid	EC 2.5.1.18 (glutathione transferase) inhibitor; ion transport inhibitor; loop diuretic
ethoxyresorufin ethoxyresorufin: structure	4.13	16	0	phenoxazine
fenoprofen Fenoprofen: A propionic acid derivative that is used as a non-steroidal anti-inflammatory agent.. fenoprofen : A monocarboxylic acid that is propanoic acid in which one of the hydrogens at position 2 is substituted by a 3-phenoxyphenyl group. A non-steroidal anti-inflammatory drug, the dihydrate form of the calcium salt is used for the management of mild to moderate pain and for the relief of pain and inflammation associated with disorders such as arthritis. It is pharmacologically similar to aspirin, but causes less gastrointestinal bleeding.	3.1	1	0	monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; non-narcotic analgesic; non-steroidal anti-inflammatory drug
berotek Fenoterol: A synthetic adrenergic beta-2 agonist that is used as a bronchodilator and tocolytic.. fenoterol : A member of the class resorcinols that is 5-(1-hydroxyethyl)benzene-1,3-diol in which one of the methyl hydrogens is replaced by a 1-(4-hydroxyphenyl)propan-2-amino group. A beta2-adrenergic agonist, it is used (as the hydrobromide salt) as a bronchodilator in the management of reversible airway obstruction.	3.1	1	0	resorcinols; secondary alcohol; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; sympathomimetic agent; tocolytic agent
fentanyl Fentanyl: A potent narcotic analgesic, abuse of which leads to habituation or addiction. It is primarily a mu-opioid agonist. Fentanyl is also used as an adjunct to general anesthetics, and as an anesthetic for induction and maintenance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1078). fentanyl : A monocarboxylic acid amide resulting from the formal condensation of the aryl amino group of N-phenyl-1-(2-phenylethyl)piperidin-4-amine with propanoic acid.	3.49	2	0	anilide; monocarboxylic acid amide; piperidines	adjuvant; anaesthesia adjuvant; anaesthetic; intravenous anaesthetic; mu-opioid receptor agonist; opioid analgesic
fluconazole Fluconazole: Triazole antifungal agent that is used to treat oropharyngeal CANDIDIASIS and cryptococcal MENINGITIS in AIDS.. fluconazole : A member of the class of triazoles that is propan-2-ol substituted at position 1 and 3 by 1H-1,2,4-triazol-1-yl groups and at position 2 by a 2,4-difluorophenyl group. It is an antifungal drug used for the treatment of mucosal candidiasis and for systemic infections including systemic candidiasis, coccidioidomycosis, and cryptococcosis.	3.76	9	0	conazole antifungal drug; difluorobenzene; tertiary alcohol; triazole antifungal drug	environmental contaminant; P450 inhibitor; xenobiotic
fluphenazine [no description available]	3.1	1	0	N-alkylpiperazine; organofluorine compound; phenothiazines	anticoronaviral agent; dopaminergic antagonist; phenothiazine antipsychotic drug
flunitrazepam Flunitrazepam: A benzodiazepine with pharmacologic actions similar to those of DIAZEPAM that can cause ANTEROGRADE AMNESIA. Some reports indicate that it is used as a date rape drug and suggest that it may precipitate violent behavior. The United States Government has banned the importation of this drug.. flunitrazepam : A 1,4-benzodiazepinone that is nitrazepam substituted by a methyl group at position 1 and by a fluoro group at position 2'. It is a potent hypnotic, sedative, and amnestic drug used to treat chronic insomnia.	2.41	2	0	1,4-benzodiazepinone; C-nitro compound; monofluorobenzenes	anxiolytic drug; GABAA receptor agonist; sedative
fluorescite fluorescein (acid form) : A xanthene dye that is highly fluorescent and commonly used as a fluorescent tracer.	3.1	1	0	benzoic acids; cyclic ketone; hydroxy monocarboxylic acid; organic heterotricyclic compound; phenols; xanthene dye	fluorescent dye; radioopaque medium
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.	2.21	1	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.	4.6	4	0	(trifluoromethyl)benzenes; aromatic ether; secondary amino compound
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.	2.05	1	0	pyrazoles	antidote; EC 1.1.1.1 (alcohol dehydrogenase) inhibitor; protective agent
furafylline [no description available]	4.83	10	0	oxopurine
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.	3.1	1	0	chlorobenzoic acid; furans; sulfonamide	environmental contaminant; loop diuretic; xenobiotic
vanoxerine vanoxerine: structure given in first source. vanoxerine : An N-alkylpiperazine that consists of piperazine bearing 2-bis(4-fluorophenyl)methoxy]ethyl and 3-phenylpropyl groups at positions 1 and 4 respectively. Potent, competitive inhibitor of dopamine uptake (Ki = 1 nM for inhibition of striatal dopamine uptake). Has > 100-fold lower affinity for the noradrenalin and 5-HT uptake carriers. Also a potent sigma ligand (IC50 = 48 nM). Centrally active following systemic administration.	2.1	1	0	ether; N-alkylpiperazine; organofluorine compound; tertiary amino compound	dopamine uptake inhibitor
guanidine Guanidine: A strong organic base existing primarily as guanidium ions at physiological pH. It is found in the urine as a normal product of protein metabolism. It is also used in laboratory research as a protein denaturant. (From Martindale, the Extra Pharmacopoeia, 30th ed and Merck Index, 12th ed) It is also used in the treatment of myasthenia and as a fluorescent probe in HPLC.. guanidine : An aminocarboxamidine, the parent compound of the guanidines.	2.07	1	0	carboxamidine; guanidines; one-carbon compound
halothane [no description available]	3.12	1	0	haloalkane; organobromine compound; organochlorine compound; organofluorine compound	inhalation anaesthetic
hexestrol [no description available]	1.96	1	0	stilbenoid
ibuprofen Midol: combination of cinnamedrine, phenacetin, aspirin & caffeine	3.1	1	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
phenelzine Phenelzine: One of the MONOAMINE OXIDASE INHIBITORS used to treat DEPRESSION; PHOBIC DISORDERS; and PANIC.	3.12	1	0	primary amine
lidocaine Lidocaine: A local anesthetic and cardiac depressant used as an antiarrhythmia agent. Its actions are more intense and its effects more prolonged than those of PROCAINE but its duration of action is shorter than that of BUPIVACAINE or PRILOCAINE.. lidocaine : The monocarboxylic acid amide resulting from the formal condensation of N,N-diethylglycine with 2,6-dimethylaniline.	1.98	1	0	benzenes; monocarboxylic acid amide; tertiary amino compound	anti-arrhythmia drug; drug allergen; environmental contaminant; local anaesthetic; 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.	4.04	4	0	dibenzoazepine	adrenergic uptake inhibitor; antidepressant; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
indole-3-carbinol indole-3-carbinol: occurs in edible cruciferous vegetables. indole-3-methanol : An indolyl alcohol carrying a hydroxymethyl group at position 3. It is a constituent of the cruciferous vegetables and had anticancer activity.	2.42	2	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.	4.97	7	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).	3.85	3	0	carbohydrazide	antitubercular agent; drug allergen
isoproterenol Isoproterenol: Isopropyl analog of EPINEPHRINE; beta-sympathomimetic that acts on the heart, bronchi, skeletal muscle, alimentary tract, etc. It is used mainly as bronchodilator and heart stimulant.. isoprenaline : A secondary amino compound that is noradrenaline in which one of the hydrogens attached to the nitrogen is replaced by an isopropyl group. A sympathomimetic acting almost exclusively on beta-adrenergic receptors, it is used (mainly as the hydrochloride salt) as a bronghodilator and heart stimulant for the management of a variety of cardiac disorders.	2	1	0	catechols; secondary alcohol; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; cardiotonic drug; sympathomimetic agent
itraconazole [no description available]	3.1	4	0	piperazines
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.	6.1	38	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.	3.1	1	0	benzophenones; oxo monocarboxylic acid	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-steroidal anti-inflammatory drug; xenobiotic
ketotifen Ketotifen: A cycloheptathiophene blocker of histamine H1 receptors and release of inflammatory mediators. It has been proposed for the treatment of asthma, rhinitis, skin allergies, and anaphylaxis.. ketotifen : An organic heterotricyclic compound that is 4,9-dihydro-10H-benzo[4,5]cyclohepta[1,2-b]thiophen-10-one which is substituted at position 4 by a 1-methylpiperidin-4-ylidene group. A blocker of histamine H1 receptors with a stabilising action on mast cells, it is used (usually as its hydrogen fumarate salt) for the treatment of asthma, where it may take several weeks to exert its full effect.	3.1	1	0	cyclic ketone; olefinic compound; organic heterotricyclic compound; organosulfur heterocyclic compound; piperidines; tertiary amino compound	anti-asthmatic drug; H1-receptor antagonist
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.	2.17	1	0	furanochromone; organic heterotricyclic compound; oxacycle	anti-asthmatic agent; bronchodilator agent; cardiovascular drug; vasodilator agent
labetalol Labetalol: A salicylamide derivative that is a non-cardioselective blocker of BETA-ADRENERGIC RECEPTORS and ALPHA-1 ADRENERGIC RECEPTORS.. labetalol : A diastereoisomeric mixture of approximately equal amounts of all four possible stereoisomers ((R,S)-labetolol, (S,R)-labetolol, (S,S)-labetalol and (R,R)-labetalol). It is an adrenergic antagonist used to treat high blood pressure.. 2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzamide : A member of the class of benzamides that is benzamide substituted by a hydroxy group at position 2 and by a 1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl group at position 5.	3.1	1	0	benzamides; benzenes; phenols; primary carboxamide; salicylamides; secondary alcohol; secondary amino compound
lamotrigine [no description available]	3.1	1	0	1,2,4-triazines; dichlorobenzene; primary arylamine	anticonvulsant; antidepressant; antimanic drug; calcium channel blocker; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; environmental contaminant; excitatory amino acid antagonist; geroprotector; non-narcotic analgesic; xenobiotic
lansoprazole Lansoprazole: A 2,2,2-trifluoroethoxypyridyl derivative of timoprazole that is used in the therapy of STOMACH ULCERS and ZOLLINGER-ELLISON SYNDROME. The drug inhibits H(+)-K(+)-EXCHANGING ATPASE which is found in GASTRIC PARIETAL CELLS. Lansoprazole is a racemic mixture of (R)- and (S)-isomers.	2.1	1	0	benzimidazoles; pyridines; sulfoxide	anti-ulcer drug; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor
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.	3.79	3	0	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; antibacterial agent; plant metabolite
leflunomide Leflunomide: An isoxazole derivative that inhibits dihydroorotate dehydrogenase, the fourth enzyme in the pyrimidine biosynthetic pathway. It is used an immunosuppressive agent in the treatment of RHEUMATOID ARTHRITIS and PSORIATIC ARTHRITIS.. leflunomide : A monocarboxylic acid amide obtained by formal condensation of the carboxy group of 5-methyl-1,2-oxazole-4-carboxylic acid with the anilino group of 4-(trifluoromethyl)aniline. The prodrug of teriflunomide.	2.06	1	0	(trifluoromethyl)benzenes; isoxazoles; monocarboxylic acid amide	antineoplastic agent; antiparasitic agent; EC 1.3.98.1 [dihydroorotate oxidase (fumarate)] inhibitor; EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; hepatotoxic agent; immunosuppressive agent; non-steroidal anti-inflammatory drug; prodrug; pyrimidine synthesis inhibitor; tyrosine kinase inhibitor
letrozole [no description available]	2.53	2	0	nitrile; triazoles	antineoplastic agent; EC 1.14.14.14 (aromatase) inhibitor
lorazepam Lorazepam: A benzodiazepine used as an anti-anxiety agent with few side effects. It also has hypnotic, anticonvulsant, and considerable sedative properties and has been proposed as a preanesthetic agent.	3.1	1	0	benzodiazepine
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	4.01	4	0	biphenylyltetrazole; imidazoles	angiotensin receptor antagonist; anti-arrhythmia drug; antihypertensive agent; endothelin receptor antagonist
loxapine Loxapine: An antipsychotic agent used in SCHIZOPHRENIA.	3.1	1	0	dibenzooxazepine	antipsychotic agent; dopaminergic antagonist
2-(4-morpholinyl)-8-phenyl-4h-1-benzopyran-4-one 2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one: specific inhibitor of phosphatidylinositol 3-kinase; structure in first source	2.02	1	0	chromones; morpholines; organochlorine compound	autophagy inhibitor; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor; geroprotector
meperidine Meperidine: A narcotic analgesic that can be used for the relief of most types of moderate to severe pain, including postoperative pain and the pain of labor. Prolonged use may lead to dependence of the morphine type; withdrawal symptoms appear more rapidly than with morphine and are of shorter duration.. pethidine : A piperidinecarboxylate ester that is piperidine which is substituted by a methyl group at position 1 and by phenyl and ethoxycarbonyl groups at position 4. It is an analgesic which is used for the treatment of moderate to severe pain, including postoperative pain and labour pain.	3.1	1	0	ethyl ester; piperidinecarboxylate ester; tertiary amino compound	antispasmodic drug; kappa-opioid receptor agonist; mu-opioid receptor agonist; opioid analgesic
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.	2.67	3	0	imidazolidine-2,4-dione	anticonvulsant
mesalamine Mesalamine: An anti-inflammatory agent, structurally related to the SALICYLATES, which is active in INFLAMMATORY BOWEL DISEASE. It is considered to be the active moiety of SULPHASALAZINE. (From Martindale, The Extra Pharmacopoeia, 30th ed). mesalamine : A monohydroxybenzoic acid that is salicylic acid substituted by an amino group at the 5-position.	3.1	1	0	amino acid; aromatic amine; monocarboxylic acid; monohydroxybenzoic acid; phenols	non-steroidal anti-inflammatory drug
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.	4.71	9	0	aromatic ether; psoralens	antineoplastic agent; cross-linking reagent; dermatologic drug; photosensitizing agent; plant metabolite
methyl methanesulfonate [no description available]	1.97	1	0	methanesulfonate ester	alkylating agent; apoptosis inducer; carcinogenic agent; genotoxin; mutagen
metoclopramide Metoclopramide: A dopamine D2 antagonist that is used as an antiemetic.. metoclopramide : A member of the class of benzamides resulting from the formal condensation of 4-amino-5-chloro-2-methoxybenzoic acid with the primary amino group of N,N-diethylethane-1,2-diamine.	3.12	1	0	benzamides; monochlorobenzenes; substituted aniline; tertiary amino compound	antiemetic; dopaminergic antagonist; environmental contaminant; gastrointestinal drug; xenobiotic
metoprolol Metoprolol: A selective adrenergic beta-1 blocking agent that is commonly used to treat ANGINA PECTORIS; HYPERTENSION; and CARDIAC ARRHYTHMIAS.. metoprolol : A propanolamine that is 1-(propan-2-ylamino)propan-2-ol substituted by a 4-(2-methoxyethyl)phenoxy group at position 1.	2.25	1	0	aromatic ether; propanolamine; secondary alcohol; secondary amino compound	antihypertensive agent; beta-adrenergic antagonist; environmental contaminant; geroprotector; xenobiotic
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.	1.97	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.	5.28	54	0	aromatic ketone	antimetabolite; diagnostic agent; EC 1.14.15.4 (steroid 11beta-monooxygenase) inhibitor
mexiletine Mexiletine: Antiarrhythmic agent pharmacologically similar to LIDOCAINE. It may have some anticonvulsant properties.. mexiletine : An aromatic ether which is 2,6-dimethylphenyl ether of 2-aminopropan-1-ol.	3.51	2	0	aromatic ether; primary amino compound	anti-arrhythmia drug
mianserin Mianserin: A tetracyclic compound with antidepressant effects. It may cause drowsiness and hematological problems. Its mechanism of therapeutic action is not well understood, although it apparently blocks alpha-adrenergic, histamine H1, and some types of serotonin receptors.. mianserin : A dibenzoazepine (specifically 1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepine) methyl-substituted on N-2. Closely related to (and now mostly superseded by) the tetracyclic antidepressant mirtazapinean, it is an atypical antidepressant used in the treatment of depression throughout Europe and elsewhere.	2	1	0	dibenzoazepine	adrenergic uptake inhibitor; alpha-adrenergic antagonist; antidepressant; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; geroprotector; H1-receptor antagonist; histamine agonist; sedative; serotonergic antagonist
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.	3.51	8	0	dichlorobenzene; ether; imidazoles
midazolam Midazolam: A short-acting hypnotic-sedative drug with anxiolytic and amnestic properties. It is used in dentistry, cardiac surgery, endoscopic procedures, as preanesthetic medication, and as an adjunct to local anesthesia. The short duration and cardiorespiratory stability makes it useful in poor-risk, elderly, and cardiac patients. It is water-soluble at pH less than 4 and lipid-soluble at physiological pH.. midazolam : An imidazobenzodiazepine that is 4H-imidazo[1,5-a][1,4]benzodiazepine which is substituted by a methyl, 2-fluorophenyl and chloro groups at positions 1, 6 and 8, respectively.	3.42	7	0	imidazobenzodiazepine; monofluorobenzenes; organochlorine compound	anticonvulsant; antineoplastic agent; anxiolytic drug; apoptosis inducer; central nervous system depressant; GABAA receptor agonist; general anaesthetic; muscle relaxant; sedative
mirtazapine Mirtazapine: A piperazinoazepine tetracyclic compound that enhances the release of NOREPINEPHRINE and SEROTONIN through blockage of presynaptic ALPHA-2 ADRENERGIC RECEPTORS. It also blocks both 5-HT2 and 5-HT3 serotonin receptors and is a potent HISTAMINE H1 RECEPTOR antagonist. It is used for the treatment of depression, and may also be useful for the treatment of anxiety disorders.	2	1	0	benzazepine; tetracyclic antidepressant	alpha-adrenergic antagonist; anxiolytic drug; H1-receptor antagonist; histamine antagonist; oneirogen; serotonergic antagonist
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.	3.1	1	0	dihydroxyanthraquinone	analgesic; antineoplastic agent
n-benzyl-1-aminobenzotriazole [no description available]	1.98	1	0
clorgyline Clorgyline: An antidepressive agent and monoamine oxidase inhibitor related to PARGYLINE.. clorgyline : An aromatic ether that is the 2,4-dichlorophenyl ether of 3-aminopropan-1-ol in which the nitrogen is substituted by a methyl group and a prop-1-yn-3-yl group. A monoamine oxidase inhibitor, it was formerly used as an antidepressant.	3.12	1	0	aromatic ether; dichlorobenzene; terminal acetylenic compound; tertiary amino compound	antidepressant; EC 1.4.3.4 (monoamine oxidase) inhibitor
nefazodone nefazodone: may be useful as an opiate adjunct	3.12	1	0	aromatic ether; monochlorobenzenes; N-alkylpiperazine; N-arylpiperazine; triazoles	alpha-adrenergic antagonist; analgesic; antidepressant; serotonergic antagonist; serotonin uptake inhibitor
nevirapine Nevirapine: A potent, non-nucleoside reverse transcriptase inhibitor used in combination with nucleoside analogues for treatment of HIV INFECTIONS and AIDS.. nevirapine : A dipyridodiazepine that is 5,11-dihydro-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepine which is substituted by methyl, oxo, and cyclopropyl groups at positions 4, 6, and 11, respectively. A non-nucleoside reverse transcriptase inhibitor with activity against HIV-1, it is used in combination with other antiretrovirals for the treatment of HIV infection.	3.25	4	0	cyclopropanes; dipyridodiazepine	antiviral drug; HIV-1 reverse transcriptase inhibitor
niclosamide Niclosamide: An antihelmintic that is active against most tapeworms. (From Martindale, The Extra Pharmacopoeia, 30th ed, p48). niclosamide : A secondary carboxamide resulting from the formal condensation of the carboxy group of 5-chlorosalicylic acid with the amino group of 2-chloro-4-nitroaniline. It is an oral anthelmintic drug approved for use against tapeworm infections.	2.08	1	0	benzamides; C-nitro compound; monochlorobenzenes; salicylanilides; secondary carboxamide	anthelminthic drug; anticoronaviral agent; antiparasitic agent; apoptosis inducer; molluscicide; piscicide; STAT3 inhibitor
nifedipine Nifedipine: A potent vasodilator agent with calcium antagonistic action. It is a useful anti-anginal agent that also lowers blood pressure.	3.08	5	0	C-nitro compound; dihydropyridine; methyl ester	calcium channel blocker; human metabolite; tocolytic agent; vasodilator agent
nisoxetine nisoxetine: potent inhibitor for norepinephrine uptake into rat brain synaptosomes & brain; NM refers to (+-)-isomer; RN given refers to parent cpd; structure. nisoxetine : A secondary amino compound that is N-methyl-3-phenylpropan-1-amine substituted at position 3 by a 2-methoxyphenoxy group.	3.85	3	0	aromatic ether; secondary amino compound	adrenergic uptake inhibitor; antidepressant
masoprocol nordihydroguaretic acid: antioxidant compound found in the creosote bush (Larrea tridentata)	2.05	1	0	catechols; lignan; tetrol	antioxidant; ferroptosis inhibitor; geroprotector; plant metabolite
nortriptyline Nortriptyline: A metabolite of AMITRIPTYLINE that is also used as an antidepressive agent. Nortriptyline is used in major depression, dysthymia, and atypical depressions.. nortriptyline : An organic tricyclic compound that is 10,11-dihydro-5H-dibenzo[a,d][7]annulene substituted by a 3-(methylamino)propylidene group at position 5. It is an active metabolite of amitriptyline.	4.02	2	0	organic tricyclic compound; secondary amine	adrenergic uptake inhibitor; analgesic; antidepressant; antineoplastic agent; apoptosis inducer; drug metabolite
o(6)-benzylguanine O(6)-benzylguanine: a suicide inhibitor of O(6)-methylguanine-DNA methyltransferase activity	2.03	1	0
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.	9.05	14	0	aromatic ether; benzimidazoles; pyridines; sulfoxide
orphenadrine Orphenadrine: A muscarinic antagonist used to treat drug-induced parkinsonism and to relieve pain from muscle spasm.. orphenadrine : A tertiary amino compound which is the phenyl-o-tolylmethyl ether of 2-(dimethylamino)ethanol.	2.69	3	0	ether; tertiary amino compound	antidyskinesia agent; antiparkinson drug; H1-receptor antagonist; muscarinic antagonist; muscle relaxant; NMDA receptor antagonist; parasympatholytic
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.	3.1	1	0	phenols; pyrazolidines	antimicrobial agent; antineoplastic agent; antipyretic; drug metabolite; gout suppressant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic metabolite
aminosalicylic acid Aminosalicylic Acid: An antitubercular agent often administered in association with ISONIAZID. The sodium salt of the drug is better tolerated than the free acid.. 4-aminosalicylic acid : An aminobenzoic acid that is salicylic acid substituted by an amino group at position 4.	3.1	1	0	aminobenzoic acid; phenols	antitubercular agent
pd 153035 4-((3-bromophenyl)amino)-6,7-dimethoxyquinazoline: structure given in first source. PD-153035 : A member of the class of quinazolines carrying a 3-bromophenylamino substituent at position 4 and two methoxy substituents at positions 6 and 7.	2.03	1	0	aromatic amine; aromatic ether; bromobenzenes; quinazolines; secondary amino compound	EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor; epidermal growth factor receptor antagonist
pd 98059 2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one: inhibits MAP kinase kinase (MEK) activity, p42 MAPK and p44 MAPK; structure in first source. 2-(2-amino-3-methoxyphenyl)chromen-4-one : A member of the class of monomethoxyflavones that is 3'-methoxyflavone bearing an additional amino substituent at position 2'.	2.42	2	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.	2.37	2	0	barbiturates	GABAA receptor agonist
perazine Perazine: A phenothiazine antipsychotic with actions and uses similar to those of CHLORPROMAZINE. Extrapyramidal symptoms may be more common than other side effects.. perazine : A phenothiazine derivative in which 10H-phenothiazinecarries a 3-(4-methylpiperazin-1-yl)propyl substituent at the N-10 position.	2.42	2	0	N-alkylpiperazine; N-methylpiperazine; phenothiazines	dopaminergic antagonist; phenothiazine antipsychotic drug
phenacetin Saridon: contains phenacetin, caffeine, propyphenazone & pyrithyldione	8.79	11	0	acetamides; aromatic ether	cyclooxygenase 3 inhibitor; non-narcotic analgesic; peripheral nervous system drug
phenazopyridine Phenazopyridine: A local anesthetic that has been used in urinary tract disorders. Its use is limited by problems with toxicity (primarily blood disorders) and potential carcinogenicity.. phenazopyridine : A diaminopyridine that is 2,6-diaminopyridine substituted at position 3 by a phenylazo group. A local anesthetic that has topical analgesic effect on mucosa lining of the urinary tract. Its use is limited by problems with toxicity (primarily blood disorders) and potential carcinogenicity.	1.98	1	0	diaminopyridine; monoazo compound	anticoronaviral agent; carcinogenic agent; local anaesthetic; non-narcotic analgesic
pheniramine Pheniramine: One of the HISTAMINE H1 ANTAGONISTS with little sedative action. It is used in treatment of hay fever, rhinitis, allergic dermatoses, and pruritus.	3.1	1	0	pyridines; tertiary amino compound
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.	11.2	45	0	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.	3.1	1	0	2,1-benzoxathiole; arenesulfonate ester; phenols; sultone	acid-base indicator; diagnostic agent; two-colour indicator
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.	3.48	2	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.	2.03	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	2.08	1	0	aromatic ketone
ag 1879 3-(4-chlorophenyl)-1-(1,1-dimethylethyl)-1H-pyrazolo(3,4-d)pyrimidin-4-amine: Fyn kinase inhibitor	2.44	2	0	aromatic amine; monochlorobenzenes; pyrazolopyrimidine	beta-adrenergic antagonist; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; geroprotector
proadifen Proadifen: An inhibitor of drug metabolism and CYTOCHROME P-450 ENZYME SYSTEM activity.	4.75	31	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.	3.51	2	0	benzoic acids; sulfonamide	uricosuric drug
promazine Promazine: A phenothiazine with actions similar to CHLORPROMAZINE but with less antipsychotic activity. It is primarily used in short-term treatment of disturbed behavior and as an antiemetic.. promazine : A phenothiazine deriative in which the phenothiazine tricycle has a 3-(dimethylaminopropyl) group at the N-10 position.	2.01	1	0	phenothiazines; tertiary amine	antiemetic; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; H1-receptor antagonist; muscarinic antagonist; phenothiazine antipsychotic drug; serotonergic antagonist
promethazine Promethazine: A phenothiazine derivative with histamine H1-blocking, antimuscarinic, and sedative properties. It is used as an antiallergic, in pruritus, for motion sickness and sedation, and also in animals.. promethazine : A tertiary amine that is a substituted phenothiazine in which the ring nitrogen at position 10 is attached to C-3 of an N,N-dimethylpropan-2-amine moiety.	3.1	1	0	phenothiazines; tertiary amine	anti-allergic agent; anticoronaviral agent; antiemetic; antipruritic drug; H1-receptor antagonist; local anaesthetic; sedative
propafenone Propafenone: An antiarrhythmia agent that is particularly effective in ventricular arrhythmias. It also has weak beta-blocking activity.. propafenone : An aromatic ketone that is 3-(propylamino)propane-1,2-diol in which the hydrogen of the primary hydroxy group is replaced by a 2-(3-phenylpropanoyl)phenyl group. It is a class 1C antiarrhythmic drug with local anesthetic effects, and is used as the hydrochloride salt in the management of supraventricular and ventricular arrhythmias.	2.69	2	0	aromatic ketone; secondary alcohol; secondary amino compound	anti-arrhythmia drug
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.	3.1	1	0	phenols	anticonvulsant; antiemetic; intravenous anaesthetic; radical scavenger; sedative
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.	4.22	5	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.	3.1	1	0	trihydroxybenzoic acid
pyrilamine Pyrilamine: A histamine H1 antagonist. It has mild hypnotic properties and some local anesthetic action and is used for allergies (including skin eruptions) both parenterally and locally. It is a common ingredient of cold remedies.. mepyramine : An ethylenediamine derivative that is ethylenediamine in which one of the amino nitrogens is substituted by two methyl groups and the remaining amino nitrogen is substituted by a 4-methoxybenzyl and a pyridin-2-yl group.	3.1	1	0	aromatic ether; ethylenediamine derivative	H1-receptor antagonist
1,2,5,8-tetrahydroxy anthraquinone 1,2,5,8-tetrahydroxy anthraquinone: structure in first source. quinalizarin : A tetrahydroxyanthraquinone having the four hydroxy groups at the 1-, 2-, 5- and 8-positions.	3.1	1	0	tetrahydroxyanthraquinone	EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor
raloxifene raloxifene : A member of the class of 1-benzothiophenes that is 1-benzothiophene in which the hydrogens at positions 2, 3, and 6 have been replaced by p-hydroxyphenyl, p-[2-(piperidin-1-yl)ethoxy]benzoyl, and hydroxy groups, respectively.	3.58	2	0	1-benzothiophenes; aromatic ketone; N-oxyethylpiperidine; phenols	bone density conservation agent; estrogen antagonist; estrogen receptor modulator
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.	2.67	3	0	benzodioxoles	flavouring agent; insecticide; metabolite; plant metabolite
salicylamide salamide: a major impurity of hydrochlorothiazide; structure in first source	3.76	3	0	phenols; salicylamides	antirheumatic drug; non-narcotic analgesic
secobarbital Secobarbital: A barbiturate that is used as a sedative. Secobarbital is reported to have no anti-anxiety activity.. secobarbital : A member of the class of barbiturates that is barbituric acid in which the hydrogens at position 5 are substituted by prop-2-en-1-yl and pentan-2-yl groups.	3.12	1	0	barbiturates	anaesthesia adjuvant; GABA modulator; sedative
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).	2.66	2	0	dicarboxylic acid diamide; hydroxamic acid	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor
sulfadimethoxine Sulfadimethoxine: A sulfanilamide that is used as an anti-infective agent.. sulfadimethoxine : A sulfonamide consisting of pyrimidine having methoxy substituents at the 2- and 6-positions and a 4-aminobenzenesulfonamido group at the 4-position.	3.1	1	0	aromatic ether; pyrimidines; substituted aniline; sulfonamide antibiotic; sulfonamide	antiinfective agent; antimicrobial agent; drug allergen; environmental contaminant; 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.	5.27	47	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
sulfathiazole Sulfathiazole: A sulfathiazole compound that is used as a short-acting anti-infective agent. It is no longer commonly used systemically due to its toxicity, but may still be applied topically in combination with other drugs for the treatment of vaginal and skin infections, and is still used in veterinary medicine.. sulfathiazole : A 1,3-thiazole compound having a 4-aminobenzenesulfonamido group at the 2-position.	3.1	1	0	1,3-thiazoles; substituted aniline; sulfonamide antibiotic; sulfonamide	antiinfective agent; drug allergen; EC 2.5.1.15 (dihydropteroate synthase) inhibitor; environmental contaminant; xenobiotic
sulfinpyrazone Sulfinpyrazone: A uricosuric drug that is used to reduce the serum urate levels in gout therapy. It lacks anti-inflammatory, analgesic, and diuretic properties.	3.1	1	0	pyrazolidines; sulfoxide	uricosuric drug
suprofen Suprofen: An IBUPROFEN-type anti-inflammatory analgesic and antipyretic. It inhibits prostaglandin synthesis and has been proposed as an anti-arthritic.. suprofen : An aromatic ketone that is thiophene substituted at C-2 by a 4-(1-carboxyethyl)benzoyl group.	4.02	2	0	aromatic ketone; monocarboxylic acid; thiophenes	antirheumatic drug; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; peripheral nervous system drug
temazepam Temazepam: A benzodiazepine that acts as a GAMMA-AMINOBUTYRIC ACID modulator and anti-anxiety agent.	3.49	2	0	benzodiazepine
terfenadine Terfenadine: A selective histamine H1-receptor antagonist devoid of central nervous system depressant activity. The drug was used for ALLERGY but withdrawn due to causing LONG QT SYNDROME.	9.03	4	0	diarylmethane
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.	2.46	2	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).	3.12	1	0	aziridines
thonzylamine thonzylamine: major descriptor (72-84); file-maintained to PYRIMIDINES	3.1	1	0	methoxybenzenes
tiaprofenic acid tiaprofenic acid: RN given refers to parent cpd; structure. tiaprofenic acid : An aromatic ketone that is thiophene substituted at C-2 by benzoyl and at C-4 by a 1-carboxyethyl group.	3.1	1	0	aromatic ketone; monocarboxylic acid; thiophenes	drug allergen; non-steroidal anti-inflammatory drug
ticlopidine Ticlopidine: An effective inhibitor of platelet aggregation commonly used in the placement of STENTS in CORONARY ARTERIES.. ticlopidine : A thienopyridine that is 4,5,6,7-tetrahydrothieno[3,2-c]pyridine in which the hydrogen attached to the nitrogen is replaced by an o-chlorobenzyl group.	4.93	10	0	monochlorobenzenes; thienopyridine	anticoagulant; fibrin modulating drug; hematologic agent; P2Y12 receptor antagonist; platelet aggregation inhibitor
tizanidine tizanidine: RN given refers to parent cpd; structure. tizanidine : 2,1,3-Benzothiadiazole substituted at C-4 by a Delta(1)-imidazolin-2-ylamino group and at C-4 by a chloro group. It is an agonist at alpha2-adrenergic receptor sites.	2.13	1	0	benzothiadiazole; imidazoles	alpha-adrenergic agonist; muscle relaxant
tolbutamide Tolbutamide: A sulphonylurea hypoglycemic agent with actions and uses similar to those of CHLORPROPAMIDE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p290). tolbutamide : An N-sulfonylurea that consists of 1-butylurea having a tosyl group attached at the 3-position.	2.69	3	0	N-sulfonylurea	human metabolite; hypoglycemic agent; insulin secretagogue; potassium channel blocker
trifluoperazine [no description available]	3.1	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
triflupromazine Triflupromazine: A phenothiazine used as an antipsychotic agent and as an antiemetic.. triflupromazine : A member of the class of phenothiazines that is 10H-phenothiazine having a trifluoromethyl subsitituent at the 2-position and a 3-(dimethylamino)propyl group at the N-10 position.	3.1	1	0	organofluorine compound; phenothiazines; tertiary amine	anticoronaviral agent; antiemetic; dopaminergic antagonist; first generation antipsychotic
trimethoprim Trimethoprim: A pyrimidine inhibitor of dihydrofolate reductase, it is an antibacterial related to PYRIMETHAMINE. It is potentiated by SULFONAMIDES and the TRIMETHOPRIM, SULFAMETHOXAZOLE DRUG COMBINATION is the form most often used. It is sometimes used alone as an antimalarial. TRIMETHOPRIM RESISTANCE has been reported.. trimethoprim : An aminopyrimidine antibiotic whose structure consists of pyrimidine 2,4-diamine and 1,2,3-trimethoxybenzene moieties linked by a methylene bridge.	2.05	1	0	aminopyrimidine; methoxybenzenes	antibacterial drug; diuretic; drug allergen; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; environmental contaminant; xenobiotic
tripelennamine Tripelennamine: A histamine H1 antagonist with low sedative action but frequent gastrointestinal irritation. It is used to treat ASTHMA; HAY FEVER; URTICARIA; and RHINITIS; and also in veterinary applications. Tripelennamine is administered by various routes, including topically.	3.1	1	0	aromatic amine
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.	2.17	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
delavirdine Delavirdine: A potent, non-nucleoside reverse transcriptase inhibitor with activity specific for HIV-1.. delavirdine : The amide resulting from the formal condensation of 5-[(methylsulfonyl)amino]-1H-indole-2-carboxylic acid and 4-amino group of 1-[3-(isopropylamino)pyridin-2-yl]piperazine, delavirdine is a non-nucleoside reverse transcriptase inhibitor with activity specific for HIV-1. Viral resistance emerges rapidly when delavirdine is used alone, so it is therefore used (as the methanesulfonic acid salt) with other antiretrovirals for combination therapy of HIV infection.	3.12	1	0	aminopyridine; indolecarboxamide; N-acylpiperazine; sulfonamide	antiviral drug; HIV-1 reverse transcriptase inhibitor
usnic acid [no description available]	2.1	1	0	benzofurans
venlafaxine venlafaxine : A tertiary amino compound that is N,N-dimethylethanamine substituted at position 1 by a 1-hydroxycyclohexyl and 4-methoxyphenyl group.	2.1	1	0	cyclohexanols; monomethoxybenzene; tertiary alcohol; tertiary amino compound	adrenergic uptake inhibitor; analgesic; antidepressant; dopamine uptake inhibitor; environmental contaminant; serotonin uptake inhibitor; xenobiotic
pirinixic acid pirinixic acid: structure	1.97	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	3.25	1	0
zomepirac zomepirac: RN given refers to parent cpd; structure	3.1	1	0	aromatic ketone; monocarboxylic acid; monochlorobenzenes; pyrroles	cardiovascular drug; non-steroidal anti-inflammatory drug
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.	1.98	1	0	mitomycin	alkylating agent; antineoplastic agent
corticosterone [no description available]	8.79	3	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
estriol hormonin: estrogen replacement; each tablet contains 600 ug micronized 17beta-estradiol, 270 ug estriol and 1.4 mg estrone. chlorapatite : A phosphate mineral with the formula Ca5(PO4)3Cl.	3.1	1	0	16alpha-hydroxy steroid; 17beta-hydroxy steroid; 3-hydroxy steroid	estrogen; human metabolite; human xenobiotic metabolite; mouse metabolite
thymidine [no description available]	2.4	2	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite
piperonyl butoxide [no description available]	3.09	5	0	benzodioxoles	pesticide synergist
2-aminophenol [no description available]	3.1	1	0	aminophenol	bacterial metabolite
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.	3.1	1	0	2-halophenol; iodophenol; L-phenylalanine derivative; non-proteinogenic L-alpha-amino acid; thyroxine zwitterion; thyroxine	antithyroid drug; human metabolite; mouse metabolite; thyroid hormone
aldosterone [no description available]	3.1	1	0	11beta-hydroxy steroid; 18-oxo steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid hormone; mineralocorticoid; primary alpha-hydroxy ketone; steroid aldehyde	human metabolite; mouse metabolite
tetrahydrocortisol [no description available]	3.1	1	0	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3alpha-hydroxy steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone
prednisone Prednisone: A synthetic anti-inflammatory glucocorticoid derived from CORTISONE. It is biologically inert and converted to PREDNISOLONE in the liver.. prednisone : A synthetic glucocorticoid drug that is particularly effective as an immunosuppressant, and affects virtually all of the immune system. Prednisone is a prodrug that is converted by the liver into prednisolone (a beta-hydroxy group instead of the oxo group at position 11), which is the active drug and also a steroid.	3.1	1	0	11-oxo steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	adrenergic agent; anti-inflammatory drug; antineoplastic agent; immunosuppressive agent; prodrug
tetrahydrocortisone [no description available]	3.1	1	0	21-hydroxy steroid
estrone Hydroxyestrones: Estrone derivatives substituted with one or more hydroxyl groups in any position. They are important metabolites of estrone and other estrogens.	4.07	4	0	17-oxo steroid; 3-hydroxy steroid; phenolic steroid; phenols	antineoplastic agent; bone density conservation agent; estrogen; human metabolite; mouse metabolite
androsterone [no description available]	3.54	2	0	17-oxo steroid; 3alpha-hydroxy steroid; androstanoid; C19-steroid	androgen; anticonvulsant; human blood serum metabolite; human metabolite; human urinary metabolite; mouse metabolite; pheromone
etiocholanolone Etiocholanolone: The 5-beta-reduced isomer of ANDROSTERONE. Etiocholanolone is a major metabolite of TESTOSTERONE and ANDROSTENEDIONE in many mammalian species including humans. It is excreted in the URINE.. 3alpha-hydroxy-5beta-androstan-17-one : An androstanoid that is 5beta-androstane substituted by an alpha-hydroxy group at position 3 and an oxo group at position 17. It is a metabolite of testosterone in mammals.	3.1	1	0	17-oxo steroid; 3alpha-hydroxy steroid; androstanoid	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.	3.77	3	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	3.51	2	0	ortho-fused polycyclic arene	mutagen
hydroxyacetylaminofluorene Hydroxyacetylaminofluorene: A N-hydroxylated derivative of 2-ACETYLAMINOFLUORENE that has demonstrated carcinogenic action.	3.48	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.	3.58	9	0	2-acetamidofluorenes	antimitotic; carcinogenic agent; epitope; mutagen
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.	3.1	1	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.	2.45	2	0	nitrosamine	carcinogenic agent; hepatotoxic agent; mutagen
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.	1.99	1	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.	2.42	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.	3.51	2	0	ortho-fused polycyclic arene; tetraphenes
chloramphenicol Amphenicol: Chloramphenicol and its derivatives.	4.53	4	0	C-nitro compound; carboxamide; diol; organochlorine compound	antibacterial drug; antimicrobial agent; Escherichia coli metabolite; geroprotector; Mycoplasma genitalium metabolite; protein synthesis inhibitor
cyanides Cyanides: Inorganic salts of HYDROGEN CYANIDE containing the -CN radical. The concept also includes isocyanides. It is distinguished from NITRILES, which denotes organic compounds containing the -CN radical.. cyanides : Salts and C-organyl derivatives of hydrogen cyanide, HC#N.. isocyanide : The isomer HN(+)#C(-) of hydrocyanic acid, HC#N, and its hydrocarbyl derivatives RNC (RN(+)#C(-)).. cyanide : A pseudohalide anion that is the conjugate base of hydrogen cyanide.	1.96	1	0	pseudohalide anion	EC 1.9.3.1 (cytochrome c oxidase) inhibitor
sucrose Saccharum: A plant genus of the family POACEAE widely cultivated in the tropics for the sweet cane that is processed into sugar.	1.97	1	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.	5.31	7	0	17-hydroxy steroid; 3-hydroxy steroid; terminal acetylenic compound	xenoestrogen
9,10-dimethyl-1,2-benzanthracene 9,10-Dimethyl-1,2-benzanthracene: Polycyclic aromatic hydrocarbon found in tobacco smoke that is a potent carcinogen.. 7,12-dimethyltetraphene : A tetraphene having methyl substituents at the 7- and 12-positions. It is a potent carcinogen and is present in tobacco smoke.	4.58	26	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.	2.39	2	0	pyrazolone; tertiary amino compound	antipyretic; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
methyltestosterone Methyltestosterone: A synthetic hormone used for androgen replacement therapy and as an hormonal antineoplastic agent (ANTINEOPLASTIC AGENTS, HORMONAL).. methyltestosterone : A 17beta-hydroxy steroid that is testosterone bearing a methyl group at the 17alpha position.	2.17	1	0	17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; enone	anabolic agent; androgen; antineoplastic agent
bromodeoxyuridine Bromodeoxyuridine: A nucleoside that substitutes for thymidine in DNA and thus acts as an antimetabolite. It causes breaks in chromosomes and has been proposed as an antiviral and antineoplastic agent. It has been given orphan drug status for use in the treatment of primary brain tumors.	2.37	2	0	pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent
p-aminoazobenzene p-Aminoazobenzene: Used in the form of its salts as a dye and as an intermediate in manufacture of Acid Yellow, diazo dyes, and indulines.. 4-(phenylazo)aniline : Azobenzene substituted at one of the 4-positions by an amino group. It has a role as a dye and an allergen.	1.97	1	0
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.	2.07	1	0	benzenes; primary alcohol	Aspergillus metabolite; fragrance; plant growth retardant; plant metabolite; Saccharomyces cerevisiae metabolite
zoxazolamine Zoxazolamine: A uricosuric and muscle relaxant. Zoxazolamine acts centrally as a muscle relaxant, but the mechanism of its action is not understood.	1.96	1	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.	2.03	1	0	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
aniline [no description available]	4.18	5	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.	2.38	2	0	nitrosamine	geroprotector; mutagen
androstenedione Androstenedione: A delta-4 C19 steroid that is produced not only in the TESTIS, but also in the OVARY and the ADRENAL CORTEX. Depending on the tissue type, androstenedione can serve as a precursor to TESTOSTERONE as well as ESTRONE and ESTRADIOL.. androst-4-ene-3,17-dione : A 3-oxo Delta(4)-steroid that is androst-4-ene substituted by oxo groups at positions 3 and 17. It is a steroid hormone synthesized in the adrenal glands and gonads.	4.16	5	0	17-oxo steroid; 3-oxo-Delta(4) steroid; androstanoid	androgen; Daphnia magna metabolite; human metabolite; mouse metabolite
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.	1.99	1	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
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.	2.42	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
desoxycorticosterone Desoxycorticosterone: A steroid metabolite that is the 11-deoxy derivative of CORTICOSTERONE and the 21-hydroxy derivative of PROGESTERONE	3.1	1	0	20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; mineralocorticoid; primary alpha-hydroxy ketone	human metabolite; mouse metabolite
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.	3.09	5	0	antibiotic fungicide; cyclic ketone; dicarboximide; piperidine antibiotic; piperidones; secondary alcohol	anticoronaviral agent; bacterial metabolite; ferroptosis inhibitor; neuroprotective agent; protein synthesis inhibitor
ficusin Ficusin: A naturally occurring furocoumarin, found in PSORALEA. After photoactivation with UV radiation, it binds DNA via single and double-stranded cross-linking.. psoralen : The simplest member of the class of psoralens that is 7H-furo[3,2-g]chromene having a keto group at position 7. It has been found in plants like Psoralea corylifolia and Ficus salicifolia.	3.57	2	0	psoralens	plant metabolite
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.	2.42	2	0	diether; tertiary amino compound; tetracarboxylic acid	chelator
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.	2	1	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.	3.1	1	0	17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; terminal acetylenic compound; tertiary alcohol	progestin; synthetic oral contraceptive
norethynodrel Norethynodrel: A synthetic progestational hormone with actions and uses similar to those of PROGESTERONE. It has been used in the treatment of functional uterine bleeding and ENDOMETRIOSIS. As a contraceptive (CONTRACEPTIVE AGENTS), it has usually been administered in combination with MESTRANOL.	3.1	1	0	oxo steroid
17-alpha-hydroxyprogesterone 17alpha-hydroxyprogesterone : A 17alpha-hydroxy steroid that is the 17alpha-hydroxy derivative of progesterone.	3.1	1	0	17alpha-hydroxy-C21-steroid; 17alpha-hydroxy steroid; tertiary alpha-hydroxy ketone	human metabolite; metabolite; mouse metabolite; progestin
ampicillin Ampicillin: Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic.. ampicillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-phenylacetamido group.	3.1	1	0	beta-lactam antibiotic; penicillin allergen; penicillin	antibacterial drug
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
alizarin [no description available]	4.06	2	0	dihydroxyanthraquinone	chromophore; dye; plant 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.	2.03	1	0	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
acetylene [no description available]	3.12	1	0	alkyne; gas molecular entity; terminal acetylenic compound
acetonitrile acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.	2	1	0	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
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.	1.95	1	0	one-carbon compound; organosulfur compound
tert-butylhydroperoxide tert-Butylhydroperoxide: A direct-acting oxidative stress-inducing agent used to examine the effects of oxidant stress on Ca(2+)-dependent signal transduction in vascular endothelial cells. It is also used as a catalyst in polymerization reactions and to introduce peroxy groups into organic molecules.. tert-butyl hydroperoxide : An alkyl hydroperoxide in which the alkyl group is tert-butyl. It is widely used in a variety of oxidation processes.	2.43	2	0	alkyl hydroperoxide	antibacterial agent; oxidising agent
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.	3.12	1	0	benzenes; piperidines	anaesthetic; neurotoxin; NMDA receptor antagonist; psychotropic drug
tri-o-cresyl phosphate tri-o-cresyl phosphate: see also related IMOL S-140	2.03	1	0
linalool linalool: RN given refers to parent cpd without isomeric designation; structure. linalool : A monoterpenoid that is octa-1,6-diene substituted by methyl groups at positions 3 and 7 and a hydroxy group at position 3. It has been isolated from plants like Ocimum canum.	3.1	1	0	monoterpenoid; tertiary alcohol	antimicrobial agent; fragrance; plant metabolite; volatile oil component
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.	3.12	1	0	chloroethenes	inhalation anaesthetic; mouse 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.	3.79	3	0	peroxol	environmental contaminant; Mycoplasma genitalium metabolite; oxidising agent
purpurin purpurin: from Rubiaceae plants; structure in first source. purpurin : A trihydroxyanthraquinone derived from anthracene by substitution with oxo groups at C-9 and C-10 and with hydroxy groups at C-1, C-2 and C-4.	3.25	1	0	trihydroxyanthraquinone	biological pigment; histological dye; plant metabolite
1,4-dihydroxyanthraquinone 1,4-dihydroxyanthraquinone: structure given in first source. quinizarin : A dihydroxyanthraquinone having the two hydroxy substituents at the 1- and 4-positions; formally derived from anthraquinone by replacement of two hydrogen atoms by hydroxy groups	3.1	1	0	dihydroxyanthraquinone	dye
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
cyclizine Cyclizine: A histamine H1 antagonist given by mouth or parenterally for the control of postoperative and drug-induced vomiting and in motion sickness. (From Martindale, The Extra Pharmacopoeia, 30th ed, p935). cyclizine : An N-alkylpiperazine in which one nitrogen of the piperazine ring is substituted by a methyl group, while the other is substituted by a diphenylmethyl group.	3.1	1	0	N-alkylpiperazine	antiemetic; central nervous system depressant; cholinergic antagonist; H1-receptor antagonist; local anaesthetic
skatole [no description available]	1.96	1	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.	1.96	1	0	organic heteropentacyclic compound; rotenones	antineoplastic agent; metabolite; mitochondrial NADH:ubiquinone reductase inhibitor; phytogenic insecticide; piscicide; toxin
2,6-dihydroxyanthraquinone 2,6-dihydroxyanthraquinone: structure given in first source. anthraflavic acid : A dihydroxyanthraquinone that is anthracene substituted by hydroxy groups at C-3 and C-7 and oxo groups at C-9 and C-10.	3.1	1	0	dihydroxyanthraquinone	antimutagen; plant metabolite
9,10-anthraquinone 9,10-anthraquinone : An anthraquinone that is anthracene in which positions 9 and 10 have been oxidised to carbonyls.	3.1	1	0	anthraquinone
thymol Thymol: A phenol obtained from thyme oil or other volatile oils used as a stabilizer in pharmaceutical preparations, and as an antiseptic (antibacterial or antifungal) agent.. thymol : A phenol that is a natural monoterpene derivative of cymene.	3.1	1	0	monoterpenoid; phenols	volatile oil component
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.	3.81	3	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.	3.1	1	0
2-phenylphenol 2-phenylphenol: RN given refers to parent cpd; structure. biphenyl-2-ol : A member of the class of hydroxybiphenyls that is biphenyl substituted by a hydroxy group at position 2. It is generally used as a post-harvest fungicide for citrus fruits.	3.1	1	0	hydroxybiphenyls	antifungal agrochemical; environmental food contaminant
quinoxalines quinoxaline : A naphthyridine in which the nitrogens are at positions 1 and 4.	2.41	2	0	mancude organic heterobicyclic parent; naphthyridine; ortho-fused heteroarene
quinoline [no description available]	3.1	1	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinolines
2-naphthylamine 2-Naphthylamine: A naphthalene derivative with carcinogenic action.. 2-naphthylamine : A naphthylamine carrying the amino group at position 2.	3.52	2	0	naphthylamine	carcinogenic agent
phenidone phenidone: photographic developer; RN given refers to parent cpd; structure	1.96	1	0
4-biphenylamine 4-biphenylamine: used in detection of sulfates, & as a carcinogen in cancer research; RN given refers to parent cpd; structure. biphenyl-4-amine : An aminobiphenyl that is biphenyl substituted by an amino group at position 4.	3.1	1	0	aminobiphenyl	carcinogenic agent
4-phenylphenol 4-phenylphenol: RN given refers to cpd without isomeric designation. biphenyl-4-ol : A member of the class of hydroxybiphenyls that is biphenyl carrying a hydroxy group at position 4.	3.1	1	0	hydroxybiphenyls
2,5-diphenyloxazole [no description available]	1.96	1	0
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.	3.1	1	0	biphenyls; substituted aniline	carcinogenic agent
4,4'-dihydroxybiphenyl biphenyl-4,4'-diol : A member of the class of hydroxybiphenyls that is biphenyl with hydroxy groups at positions 4 and 4'.	3.1	1	0	hydroxybiphenyls
methyleugenol methyleugenol: structure	2.03	1	0	phenylpropanoid
propylparaben Parabens: Methyl, propyl, butyl, and ethyl esters of p-hydroxybenzoic acid. They have been approved by the FDA as antimicrobial agents for foods and pharmaceuticals. (From Hawley's Condensed Chemical Dictionary, 11th ed, p872)	3.1	1	0	benzoate ester; paraben; phenols	antifungal agent; antimicrobial agent
4-butyrolactone 4-Butyrolactone: One of the FURANS with a carbonyl thereby forming a cyclic lactone. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent.. tetrahydrofuranone : Any oxolane having an oxo- substituent at any position on the tetrahydrofuran ring.. gamma-butyrolactone : A butan-4-olide that is tetrahydrofuran substituted by an oxo group at position 2.	2.45	2	0	butan-4-olide	metabolite; neurotoxin
butylphen butylphen: irritant; structure. 4-tert-butylphenol : A member of the class of phenols that is phenol substituted with a tert-butyl group at position 4.	3.1	1	0	phenols	allergen
methyl gallate methyl gallate: has both immunosuppressive and phytogenic antineoplastic activities; isolated from Acer saccharinum. methyl 3,4,5-trihydroxybenzoate : A gallate ester obtained by the formal condensation of gallic acid with methanol. It exhibits anti-oxidant, anti-tumor, anti-microbial and anti-inflammatory properties.	1.99	1	0	gallate ester	anti-inflammatory agent; antioxidant; plant metabolite
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.	3.1	1	0	paraben	antifungal agent; antimicrobial food preservative; neuroprotective agent; plant metabolite
4-isopropylphenol [no description available]	3.1	1	0	phenols	flavouring agent
4-hydroxyacetophenone 4-hydroxyacetophenone: promotes secretion of bile & bile salts, which promotes griseofulvin absorption in the duodenum. 4'-hydroxyacetophenone : A monohydroxyacetophenone carrying a hydroxy substituent at position 4'.	3.1	1	0	monohydroxyacetophenone	fungal metabolite; mouse metabolite; plant metabolite
4-nitrophenetol [no description available]	1.96	1	0
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.	2.41	2	0	styrenes; vinylarene; volatile organic compound	mouse metabolite; mutagen; plant metabolite
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.	2.38	2	0	chloroaniline	metabolite
4-benzylphenol 4-benzylphenol: metabolite of diphenylmethane; RN given refers to parent cpd	3.1	1	0
phenetole phenetole : An aromatic ether in which the ether oxygen is bonded to an ethyl and a phenyl group.	1.98	1	0	aromatic ether
2-ethylhexanol [no description available]	3.1	1	0	primary alcohol	plant metabolite; volatile oil component
4-vinyl-1-cyclohexene dioxide 4-vinyl-1-cyclohexene dioxide: activates caspase cascades; structure. 4-vinylcyclohexene dioxide : The diepoxide of 4-vinylcyclohexene.	2.02	1	0	epoxide	carcinogenic agent
3-phenylenediamine 1,3-phenylenediamine : A phenylenediamine taht is benzene substituted at positions 1 and 3 with amino functions.	1.97	1	0	phenylenediamine
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.	2.39	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.	2.37	2	0	cyclic ether; oxolanes; saturated organic heteromonocyclic parent; volatile organic compound	polar aprotic solvent
2,2,2-trichloroethanol [no description available]	3.1	1	0	chloroethanol	mouse metabolite
anthrarufin 1,5-dihydroxyanthraquinone: used in ferric ion sensing as an inclusion complex with beta-cyclodextrin; structure in first source. anthrarufin : A dihydroxyanthraquinone that is anthracene-9,10-dione substituted by hydroxy groups at positions 1 and 5.	3.1	1	0	dihydroxyanthraquinone
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.	2.37	2	0	aromatic fungicide; chlorobenzenes	antifungal agrochemical; carcinogenic agent; persistent organic pollutant
2-toluic acid 2-toluic acid: RN given refers to parent cpd; structure. o-toluic acid : A methylbenzoic acid that is benzoic acid substituted by a methyl group at position 2.	3.1	1	0	methylbenzoic acid	xenobiotic metabolite
ethyl-p-hydroxybenzoate ethyl-p-hydroxybenzoate: structure	3.1	1	0	ethyl ester; paraben	antifungal agent; antimicrobial food preservative; phytoestrogen; plant metabolite
3-tert-butyl-4-hydroxyanisole 3-tert-butyl-4-hydroxyanisole : An aromatic ether that is 4-methoxyphenol in which one of the hydrogens ortho- to the phenolic hydroxy group is replaced by a tert-butyl group.	3.1	1	0	aromatic ether; phenols	antioxidant; human xenobiotic metabolite
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.	3.1	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.	3.81	3	0	naphthol	antinematodal drug; genotoxin; human urinary metabolite; human xenobiotic metabolite; mouse metabolite; radical scavenger
shikimic acid Shikimic Acid: A tri-hydroxy cyclohexene carboxylic acid important in biosynthesis of so many compounds that the shikimate pathway is named after it.. shikimic acid : A cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid substituted by hydroxy groups at positions 3, 4 and 5 (the 3R,4S,5R stereoisomer). It is an intermediate metabolite in plants and microorganisms.	3.1	1	0	alpha,beta-unsaturated monocarboxylic acid; cyclohexenecarboxylic acid; hydroxy monocarboxylic acid	Escherichia coli metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
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.	3.1	1	0	monoterpenoid	plant metabolite
hexanoic acid hexanoic acid : A C6, straight-chain saturated fatty acid.	3.1	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	human metabolite; plant metabolite
pregnenolone [no description available]	3.49	2	0	20-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; C21-steroid	human metabolite; mouse metabolite
diphenhydramine hydrochloride Antitussive Agents: Agents that suppress cough. They act centrally on the medullary cough center. EXPECTORANTS, also used in the treatment of cough, act locally.. diphenhydramine hydrochloride : The hydrochloride salt of diphenhydramine.	2.41	2	0	hydrochloride; organoammonium salt	anti-allergic agent; antiemetic; antiparkinson drug; antipruritic drug; H1-receptor antagonist; local anaesthetic; muscarinic antagonist; sedative
ditiocarb Ditiocarb: A chelating agent that has been used to mobilize toxic metals from the tissues of humans and experimental animals. It is the main metabolite of DISULFIRAM.. diethyldithiocarbamic acid : A member of the class of dithiocarbamic acids that is diethylcarbamic acid in which both of the oxygens are replaced by sulfur.	5.8	17	0	dithiocarbamic acids	chelator; copper chelator
mequinol mequinol: depigmenting agent; RN given refers to parent cpd	3.1	1	0	methoxybenzenes; phenols	metabolite
potassium cyanide [no description available]	2.67	3	0	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
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.	4.34	6	0	catechin	antioxidant; plant metabolite
phenetidine Phenetidine: Used in the manufacture of acetophenetidin.. 4-ethoxyaniline : An aromatic ether that is aniline in which the hydrogen at position 4 is replaced by an ethoxy group. It is a hydrolysis metabolite of phenacetin.	3.1	1	0	aromatic ether; primary amino compound; substituted aniline	drug metabolite
dibenzo(a,i)pyrene [no description available]	1.96	1	0	ortho- and peri-fused polycyclic arene
dibenzo(a,h)pyrene dibenzo(a,h)pyrene: structure given in first source	1.96	1	0	ortho- and peri-fused polycyclic arene
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.	2.37	2	0	ortho- and peri-fused polycyclic arene	carcinogenic agent; mutagen
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.	2.03	1	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinazolines
cyclohexene oxide cyclohexene oxide: inhibitor of epoxide hydrase; structure	2	1	0
isoxazoles Isoxazoles: Azoles with an OXYGEN and a NITROGEN next to each other at the 1,2 positions, in contrast to OXAZOLES that have nitrogens at the 1,3 positions.. isoxazole : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing three carbon atoms and an oxygen and nitrogen atom adjacent to each other. It is the parent of the class of isoxazoles.. isoxazoles : Oxazoles in which the N and O atoms are adjacent.	2.06	1	0	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.	1.96	1	0	1,3-oxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
thiazoles [no description available]	2	1	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.	2.44	2	0	diazine; pyrazines	Daphnia magna metabolite
paraoxon [no description available]	1.96	1	0	aryl dialkyl phosphate; organophosphate insecticide	EC 3.1.1.7 (acetylcholinesterase) inhibitor; mouse metabolite
monocrotaline Monocrotaline: A pyrrolizidine alkaloid and a toxic plant constituent that poisons livestock and humans through the ingestion of contaminated grains and other foods. The alkaloid causes pulmonary artery hypertension, right ventricular hypertrophy, and pathological changes in the pulmonary vasculature. Significant attenuation of the cardiopulmonary changes are noted after oral magnesium treatment.	2.03	1	0	pyrrolizidine alkaloid
betamethasone Betamethasone: A glucocorticoid given orally, parenterally, by local injection, by inhalation, or applied topically in the management of various disorders in which corticosteroids are indicated. Its lack of mineralocorticoid properties makes betamethasone particularly suitable for treating cerebral edema and congenital adrenal hyperplasia. (From Martindale, The Extra Pharmacopoeia, 30th ed, p724)	2.36	2	0	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; fluorinated steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	anti-asthmatic agent; anti-inflammatory drug; immunosuppressive agent
4-hydroxyphenobarbital [no description available]	3.1	1	0	barbiturates
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.	3.1	1	0	bile acid; C24-steroid; monohydroxy-5beta-cholanic acid	geroprotector; human metabolite; mouse metabolite
dextropropoxyphene Dextropropoxyphene: A narcotic analgesic structurally related to METHADONE. Only the dextro-isomer has an analgesic effect; the levo-isomer appears to exert an antitussive effect.. propoxyphene : A racemate of the (1R,2R)- and (1S,2R)- diastereoisomers.. dextropropoxyphene : The (1S,2R)-(+)-diastereoisomer of propoxyphene.	1.97	1	0	1-benzyl-3-(dimethylamino)-2-methyl-1-phenylpropyl propanoate	mu-opioid receptor agonist; opioid analgesic
chenodeoxycholic acid Chenodeoxycholic Acid: A bile acid, usually conjugated with either glycine or taurine. It acts as a detergent to solubilize fats for intestinal absorption and is reabsorbed by the small intestine. It is used as cholagogue, a choleretic laxative, and to prevent or dissolve gallstones.. chenodeoxycholic acid : A dihydroxy-5beta-cholanic acid that is (5beta)-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 7 respectively.. chenodeoxycholate : Conjugate base of chenodeoxycholic acid; major species at pH 7.3.	3.1	1	0	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
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.	2.17	1	0	hydroxy-1,4-naphthoquinone	acaricide; antibacterial agent; antineoplastic agent; apoptosis inducer; geroprotector; plant metabolite
epitestosterone Epitestosterone: The 17-alpha isomer of TESTOSTERONE, derived from PREGNENOLONE via the delta5-steroid pathway, and via 5-androstene-3-beta,17-alpha-diol. Epitestosterone acts as an antiandrogen in various target tissues. The ratio between testosterone/epitestosterone is used to monitor anabolic drug abuse.. epitestosterone : An androstanoid that is the C-17 epimer of testosterone.	3.1	1	0	17alpha-hydroxy steroid; 3-oxo-Delta(4) steroid; androstanoid	androgen antagonist; human metabolite
plumbagin plumbagin: a superoxide anion generator. plumbagin : A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 2 and 5 are substituted by methyl and hydroxy groups, respectively.	2.17	1	0	hydroxy-1,4-naphthoquinone; phenols	anticoagulant; antineoplastic agent; immunological adjuvant; metabolite
chrysophanic acid chrysophanic acid: RN given refers to parent cpd; structure in Merck, 9th ed, #2260. chrysophanol : A trihydroxyanthraquinone that is chrysazin with a methyl substituent at C-3. It has been isolated from Aloe vera and exhibits antiviral and anti-inflammatory activity.	3.1	1	0	dihydroxyanthraquinone	anti-inflammatory agent; antiviral agent; plant metabolite
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.	3.66	2	0	psoralens	EC 3.1.1.7 (acetylcholinesterase) inhibitor; metabolite
retene retene: structure in first source	2.75	3	0
osthol osthol: from Cnidium monnieri and Angelica pubescens (both Apiaceae); structure given in first source	2.17	1	0	botanical anti-fungal agent; coumarins	metabolite
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)	3.12	1	0	phthalazines
beta-nicotyrine [no description available]	3.12	1	0	pyridines
flavanone flavanone: RN given refers to cpd with unspecified isomeric designation; structure in first source. flavanone : The simplest member of the class of flavanones that consists of flavan bearing an oxo substituent at position 4.	2.71	3	0	flavanones
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).	3.1	1	0	botanical anti-fungal agent; p-menthane monoterpenoid; phenols	agrochemical; antimicrobial agent; flavouring agent; TRPA1 channel agonist; volatile oil component
medroxyprogesterone [no description available]	1.95	1	0	17alpha-hydroxy steroid; 20-oxo steroid; 3-oxo-Delta(4) steroid; tertiary alpha-hydroxy ketone	contraceptive drug; progestin; synthetic oral contraceptive
androstenediol Androstenediol: An intermediate in TESTOSTERONE biosynthesis, found in the TESTIS or the ADRENAL GLANDS. Androstenediol, derived from DEHYDROEPIANDROSTERONE by the reduction of the 17-keto group (17-HYDROXYSTEROID DEHYDROGENASES), is converted to TESTOSTERONE by the oxidation of the 3-beta hydroxyl group to a 3-keto group (3-HYDROXYSTEROID DEHYDROGENASES).. androst-5-ene-3beta,17beta-diol : A 3beta-hydroxy-Delta(5)-steroid that is 3beta-hydroxyandrost-5-ene carrying an additional hydroxy group at position 17beta.	3.1	1	0	17beta-hydroxy steroid; 3beta-hydroxy-Delta(5)-steroid	androgen; human metabolite; mouse metabolite; radiation protective agent
dihydrotestosterone Dihydrotestosterone: A potent androgenic metabolite of TESTOSTERONE. It is produced by the action of the enzyme 3-OXO-5-ALPHA-STEROID 4-DEHYDROGENASE.. 17beta-hydroxyandrostan-3-one : A 17beta-hydroxy steroid that is testosterone in which the 4-5 double bond has been reduced to a single bond with unspecified configuration at position 5.. 17beta-hydroxy-5alpha-androstan-3-one : A 17beta-hydroxy steroid that is testosterone in which the 4,5 double bond has been reduced to a single bond with alpha-configuration at position 5.	3.79	3	0	17beta-hydroxy steroid; 17beta-hydroxyandrostan-3-one; 3-oxo-5alpha-steroid	androgen; Daphnia magna metabolite; human metabolite; mouse metabolite
angelicin angelicin: used as tranquillizer; sedative; or anticonvulsant; structure	2.17	1	0	furanocoumarin
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.	4.81	10	0	flavones	metabolite; nematicide
1,2,3,4-tetrahydro-1-naphthalenol 1,2,3,4-tetrahydro-1-naphthalenol: structure in first source	3.1	1	0
chlormethiazole Chlormethiazole: A sedative and anticonvulsant often used in the treatment of alcohol withdrawal. Chlormethiazole has also been proposed as a neuroprotective agent. The mechanism of its therapeutic activity is not entirely clear, but it does potentiate GAMMA-AMINOBUTYRIC ACID receptors response and it may also affect glycine receptors.	2.06	1	0	thiazoles
hydroxyhydroquinone benzene-1,2,4-triol : A benzenetriol carrying hydroxy groups at positions 1, 2 and 4.	1.99	1	0	benzenetriol	mouse metabolite
perillyl alcohol perillyl alcohol: inhibits geranylgeranyl transferase; structure in first source. perillyl alcohol : A limonene monoterpenoid consists of a cyclohexene ring substituted by a hydroxymethyl and a prop-1-en-2-yl group at positions 1 and 4 respectively. It is a constituent of a variety of essential oils including lavender.	3.25	1	0	limonene monoterpenoid	plant metabolite; volatile oil component
4-iodophenol [no description available]	3.1	1	0	iodophenol
aminoacetonitrile Aminoacetonitrile: Cyanomethylamine.	1.96	1	0
malondialdehyde Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.	2.77	3	0	dialdehyde	biomarker
myristic acid Myristic Acid: A saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. It is used to synthesize flavor and as an ingredient in soaps and cosmetics. (From Dorland, 28th ed). tetradecanoic acid : A straight-chain, fourteen-carbon, long-chain saturated fatty acid mostly found in milk fat.. tetradecanoate : A long-chain fatty acid anion that is the conjugate base of myristic acid; major species at pH 7.3.	3.1	1	0	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite
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.	1.97	1	0	hydrochloride	acid-base indicator; dye; two-colour indicator
4-methyl-1-(1-methylethyl)-3-cyclohexen-1-ol 4-methyl-1-(1-methylethyl)-3-cyclohexen-1-ol: structure in first source. 4-terpineol : A terpineol that is 1-menthene carrying a hydroxy substituent at position 4.	3.1	1	0	terpineol; tertiary alcohol	anti-inflammatory agent; antibacterial agent; antineoplastic agent; antioxidant; antiparasitic agent; apoptosis inducer; plant metabolite; volatile oil component
formestane [no description available]	3.07	1	0	17-oxo steroid; 3-oxo-Delta(4) steroid; enol; hydroxy steroid	antineoplastic agent; EC 1.14.14.14 (aromatase) inhibitor
7-hydroxymethyl-12-methylbenz(a)anthracene [no description available]	1.95	1	0	phenanthrenes
3-hydroxyflavone 3-hydroxyflavone: structure given in first source. flavonol : A monohydroxyflavone that is the 3-hydroxy derivative of flavone.	4.36	3	0	flavonols; monohydroxyflavone
6-hydroxyquinoline quinolin-6-ol : A monohydroxyquinoline that is quinoline substituted by a hydroxy group at position 6.	3.1	1	0	monohydroxyquinoline
3-hydroxybiphenyl 3-hydroxybiphenyl: structure given in first source. biphenyl-3-ol : A member of the class of hydroxybiphenyls that is phenol in which the hydrogen at position 3 has been replaced by a phenyl group.	3.1	1	0	hydroxybiphenyls
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.	3.1	1	0	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
2-anthramine 2-anthramine: structure	3.08	5	0	anthracenamine
4-methoxybiphenyl [no description available]	1.96	1	0
4-methoxy-3-phenylenediamine 4-methoxy-3-phenylenediamine: RN given refers to parent cpd	1.95	1	0	methoxybenzenes
2-methylbenzimidazole [no description available]	2	1	0	benzimidazoles
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	3.28	6	0	acetylcysteine; L-cysteine derivative; N-acetyl-L-amino acid	antidote to paracetamol poisoning; antiinfective agent; antioxidant; antiviral drug; ferroptosis inhibitor; geroprotector; human metabolite; mucolytic; radical scavenger; vulnerary
2,6-dichloro-4-nitrophenol [no description available]	1.98	1	0
dicarbethoxydihydrocollidine Dicarbethoxydihydrocollidine: 1,4-Dihydro-2,4,6-trimethyl-3,5-pyridinedicarboxylic acid diethyl ester.. 3,5-diethoxycarbonyl-1,4-dihydrocollidine : A dihydropyridine that is 2,4,6-trimethyl-1,4-dihydropyridine substituted by ethoxycarbonyl groups at positions 3 and 5.	1.99	1	0	dihydropyridine; ethyl ester	hepatic steatosis inducing agent
Berberine chloride (TN) [no description available]	2.47	2	0	organic molecular entity
n-phenylpyrrole N-phenylpyrrole: structure in first source	1.96	1	0
benzydamine Benzydamine: A benzyl-indazole having analgesic, antipyretic, and anti-inflammatory effects. It is used to reduce post-surgical and post-traumatic pain and edema and to promote healing. It is also used topically in treatment of RHEUMATIC DISEASES and INFLAMMATION of the mouth and throat.. benzydamine : A member of the class of indazoles carrying benzyl and 3-(dimethylamino)propyl groups at positions 1 and 3 respectively. A locally-acting nonsteroidal anti-inflammatory drug that also exhibits local anaesthetic and analgesic properties.	2.25	1	0	aromatic ether; indazoles; tertiary amino compound	analgesic; central nervous system stimulant; hallucinogen; local anaesthetic; non-steroidal anti-inflammatory drug
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.	4.92	6	0	cyclic ketone; erythromycin
4-propylphenol 4-propylphenol: structure given in first source	3.1	1	0	alkylbenzene
1,4-androstadiene-3,17-dione 1,4-androstadiene-3,17-dione: structure. androsta-1,4-diene-3,17-dione : A steroid that consists of androstane having double bonds at positions 1 and 4 and two keto groups at positions 3 and 17.	3.07	1	0	17-oxo steroid; 3-oxo-Delta(1) steroid; 3-oxo-Delta(4) steroid
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.	3.1	1	0	organofluorine compound; secondary alcohol	drug metabolite
ethambutol Ethambutol: An antitubercular agent that inhibits the transfer of mycolic acids into the cell wall of the tubercle bacillus. It may also inhibit the synthesis of spermidine in mycobacteria. The action is usually bactericidal, and the drug can penetrate human cell membranes to exert its lethal effect. (From Smith and Reynard, Textbook of Pharmacology, 1992, p863). ethambutol : An ethylenediamine derivative that is ethane-1,2-diamine in which one hydrogen attached to each of the nitrogens is sutstituted by a 1-hydroxybutan-2-yl group (S,S-configuration). It is a bacteriostatic antimycobacterial drug, effective against Mycobacterium tuberculosis and some other mycobacteria. It is used (as the dihydrochloride salt) in combination with other antituberculous drugs in the treatment of pulmonary and extrapulmonary tuberculosis; resistant strains of M. tuberculosis are readily produced if ethambutol is used alone.	2.03	1	0	ethanolamines; ethylenediamine derivative	antitubercular agent; environmental contaminant; xenobiotic
ethidium bromide [no description available]	2.02	1	0	organic bromide salt	geroprotector; intercalator; trypanocidal drug
vancomycin Vancomycin: Antibacterial obtained from Streptomyces orientalis. It is a glycopeptide related to RISTOCETIN that inhibits bacterial cell wall assembly and is toxic to kidneys and the inner ear.. vancomycin : A complex glycopeptide from Streptomyces orientalis. It inhibits a specific step in the synthesis of the peptidoglycan layer in the Gram-positive bacteria Staphylococcus aureus and Clostridium difficile.	2.17	1	0	glycopeptide	antibacterial drug; antimicrobial agent; bacterial 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.	3.79	3	0	alpha-tocopherol	algal metabolite; antiatherogenic agent; anticoagulant; antioxidant; antiviral agent; EC 2.7.11.13 (protein kinase C) inhibitor; immunomodulator; micronutrient; nutraceutical; plant metabolite
n-methylcarbazole N-methylcarbazole: RN given refers to cpd with methyl group in position 9	3.12	1	0
1-aminopyrene [no description available]	2.1	1	0
fenchol fenchol: RN given refers to cpd with unspecified isomeric designation	3.1	1	0
4-n-Butylphenol [no description available]	3.1	1	0	phenols
4-hydroxyazobenzene 4-hydroxyazobenzene: structure in first source	3.1	1	0
2,3,7,8-tetrachlorodibenzodioxine Tetrachlorodibenzodioxin: A mixture of isomers.	2.13	1	0	polychlorinated dibenzodioxine
4-nitrothiophenolate 4-nitrothiophenolate: RN given refers to parent cpd	3.1	1	0
5 alpha-androstane-3 alpha,17 beta-diol 5alpha-androstane-3alpha,17beta-diol : The 5alpha-stereoisomer of androstane-3alpha,17beta-diol.	3.1	1	0	androstane-3alpha,17beta-diol	Daphnia magna metabolite; human metabolite
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.	3.25	1	0	benzochromene; diterpenoid; phytocannabinoid; polyketide	cannabinoid receptor agonist; epitope; hallucinogen; metabolite; non-narcotic analgesic
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.	2.01	1	0	aromatic amine; guanidines; organochlorine compound; pyrazines	diuretic; sodium channel blocker
4-chlorobiphenyl 4-chlorobiphenyl : A monochlorobiphenyl carrying a chloro substituent at position 4.	2.04	1	0	monochlorobiphenyl
diallyl disulfide diallyl disulfide: major constituent of garlic oil. diallyl disulfide : An organic disulfide where the organic group specified is allyl. It has been isolated from garlic and other species of the genus Allium.	2	1	0	organic disulfide	antifungal agent; antineoplastic agent; plant metabolite
menthol (+-)-menthol : A racemate comprising equimolar amounts of (+)- and (-)-menthol. Both (+-)- and (-)-menthol are used to relieve symptoms of conditions such as bronchitis and sinusitis. When applied to the skin, menthol dilates the blood vessels, giving a sensation of coldness followed by an analgesic effect that relieves itching. It is therefore used in creams and ointments for the relief of pruritis and urticaria.. (-)-menthol : A p-menthan-3-ol which has (1R,2S,5R)-stereochemistry. It is the most common naturally occurring enantiomer.	3.1	1	0	p-menthan-3-ol	antipruritic drug; antispasmodic drug; antitussive
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.	3.12	1	0	isothiocyanate	antineoplastic agent; EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor; metabolite
mirex Mirex: An organochlorine insecticide that is carcinogenic.	1.97	1	0	chlorocarbon; organochlorine insecticide	persistent organic pollutant
2,4,2',4'-tetrachlorobiphenyl 2,4,2',4'-tetrachlorobiphenyl: structure. 2,2',4,4'-tetrachlorobiphenyl : A tetrachlorobiphenyl that is biphenyl in which each of the phenyl groups is substituted at positions 2 and 4 by chlorines.	1.97	1	0	dichlorobenzene; tetrachlorobiphenyl
6-chrysenamine 6-chrysenamine: may cause splenic atrophy and leukopenia; minor descriptor (76-84); on-line & Index Medicus search PHENANTHRENES (76-84)	2.38	2	0	carbopolycyclic compound
hydroxyphenytoin hydroxyphenytoin: main metabolite of diphenylhydantoin; reduces Na(+) inhibition at high Na:K ratios; RN given refers to cpd without isomeric designation; structure. 4-hydroxyphenytoin : A imidazolidine-2,4-dione that consists of hydantoin bearing phenyl and 4-hydroxyphenyl substituents at position 5.	3.1	1	0	imidazolidine-2,4-dione; phenols	metabolite
trichloroepoxypropane Trichloroepoxypropane: A potent epoxide hydrase and aryl hydrocarbon hydroxylase inhibitor. It enhances the tumor-initiating ability of certain carcinogens.	2.65	3	0
palmatine burasaine: structure in first source	2.11	1	0	berberine alkaloid; organic heterotetracyclic compound	plant metabolite
3-methoxy-4-aminoazobenzene [no description available]	1.97	1	0
tranylcypromine Tranylcypromine: A propylamine formed from the cyclization of the side chain of amphetamine. This monoamine oxidase inhibitor is effective in the treatment of major depression, dysthymic disorder, and atypical depression. It also is useful in panic and phobic disorders. (From AMA Drug Evaluations Annual, 1994, p311). tranylcypromine : A racemate comprising equal amounts of (1R,2S)- and (1S,2R)-2-phenylcyclopropan-1-amine. An irreversible monoamine oxidase inhibitor that is used as an antidepressant (INN tranylcypromine).. (1R,2S)-tranylcypromine : A 2-phenylcyclopropan-1-amine that is the (1R,2S)-enantiomer of tranylcypromine.	3.33	6	0	2-phenylcyclopropan-1-amine
streptomycin [no description available]	2.03	1	0	antibiotic antifungal drug; antibiotic fungicide; streptomycins	antibacterial drug; antifungal agrochemical; antimicrobial agent; antimicrobial drug; bacterial metabolite; protein synthesis inhibitor
mono-(2-ethylhexyl)phthalate mono-(2-ethylhexyl)phthalate: RN given refers to parent cpd. mono(2-ethylhexyl) phthalate : The mono(2-ethylhexyl) ester of benzene-1,2-dicarboxylic acid.	3.1	1	0	phthalic acid monoester
1-naphthalenemethanol 1-naphthalenemethanol: structure given in first source. (1-naphthyl)methanol : A naphthylmethanol that is methanol in which one of the hydrogens of the methyl group is replaced by a naphthalen-1-yl group.	3.1	1	0	naphthylmethanol	mouse metabolite
dexpropranolol [no description available]	3.1	1	0	propranolol
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.	2.05	1	0	diastereoisomeric mixture; homocysteines; non-proteinogenic alpha-amino acid; sulfoximide	EC 6.3.2.2 (glutamate--cysteine ligase) inhibitor; ferroptosis inducer
1-nitropyrene [no description available]	2.1	1	0	nitroarene	carcinogenic agent
coralyne [no description available]	2.02	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.	1.96	1	0	elemental manganese; manganese group element atom	Escherichia coli metabolite; micronutrient
cadmium Cadmium: An element with atomic symbol Cd, atomic number 48, and atomic weight 112.41. It is a metal and ingestion will lead to CADMIUM POISONING.. elemental cadmium : An element in the zinc group of the periodic table with atomic number 48, atomic mass 112, M.P. 321degreeC, and B.P. 765degreeC). An odourless, tasteless, and highly poisonous soft, ductile, lustrous metal with electropositive properties. It has eight stable isotopes: (106)Cd, (108)Cd,(110)Cd, (111)Cd, (112)Cd, (113)Cd, (114)Cd and (116)Cd, with (112)Cd and (114)Cd being the most common.	2.38	2	0	cadmium molecular entity; zinc group element atom
galactosamine 2-amino-2-deoxy-D-galactopyranose : The pyranose form of D-galactosamine.. D-galactosamine : The D-stereoisomer of galactosamine.	1.96	1	0	D-galactosamine; primary amino compound	toxin
butylated hydroxyanisole [no description available]	3.1	1	0
cadmium sulfate cadmium sulfate: RN given refers to cpd with MF of Cd-H2SO4	2.42	2	0	cadmium salt
3-hydroxybenzo(a)pyrene 3-hydroxybenzo(a)pyrene: RN given refers to unlabeled parent cpd	4.49	4	0	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	3.58	9	0	pyrenes
selegiline Selegiline: A selective, irreversible inhibitor of Type B monoamine oxidase that is used for the treatment of newly diagnosed patients with PARKINSON DISEASE, and for the treatment of depressive disorders. The compound without isomeric designation is Deprenyl.	3.12	1	0	selegiline; terminal acetylenic compound	geroprotector
4-n-Pentylphenol [no description available]	3.1	1	0	phenols
tetradecanoylphorbol acetate Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.	3.35	7	0	acetate ester; diester; phorbol ester; tertiary alpha-hydroxy ketone; tetradecanoate ester	antineoplastic agent; apoptosis inducer; carcinogenic agent; mitogen; plant metabolite; protein kinase C agonist; reactive oxygen species generator
2-chloro-4-acetotoluidine [no description available]	1.97	1	0
9-hydroxybenzo(a)pyrene 9-hydroxybenzo(a)pyrene: RN given refers to unlabeled parent cpd	4	2	0	ortho- and peri-fused polycyclic arene
stilbene oxide stilbene oxide: inducer of epoxide hydratase; RN given refers to cpd without isomeric designation	1.96	1	0	epoxide
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.	3.1	1	0	aminoglycoside antibiotic; anthracycline; p-quinones; tetracenequinones	antineoplastic agent; bacterial metabolite
n-phenylethanolamine [no description available]	3.1	1	0	aralkylamine
4-ethylphenol 4-ethylphenol: RN given refers to parent cpd. 4-ethylphenol : A member of the class of phenols carrying an ethyl substituent at position 4.	3.1	1	0	phenols	fungal xenobiotic metabolite
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.	3.1	1	0	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
pregnanolone Pregnanolone: A pregnane found in the urine of pregnant women and sows. It has anesthetic, hypnotic, and sedative properties.. 3alpha-hydroxy-5beta-pregnan-20-one : The 3alpha-stereoisomer of 3-hydroxy-5beta-pregnan-20-one.	3.48	2	0	3-hydroxy-5beta-pregnan-20-one; 3alpha-hydroxy steroid	human metabolite; intravenous anaesthetic; sedative
butylated hydroxytoluene 2,6-di-tert-butyl-4-methylphenol : A member of the class of phenols that is 4-methylphenol substituted by tert-butyl groups at positions 2 and 6.	3.1	1	0	phenols	antioxidant; ferroptosis inhibitor; food additive; geroprotector
pyrene pyrene: structure in Merck Index, 9th ed, #7746. pyrene : An ortho- and peri-fused polycyclic arene consisting of four fused benzene rings, resulting in a flat aromatic system.	4.35	3	0	ortho- and peri-fused polycyclic arene	fluorescent probe; persistent organic pollutant
9,10-dihydro-9,10-dihydroxybenzo(a)pyrene 9,10-dihydro-9,10-dihydroxybenzo(a)pyrene: RN given refers to cpd without isomeric designation	1.96	1	0
oxypeucadanin, (s)-(-)-isomer [no description available]	2.17	1	0	epoxide; furanocoumarin; lactone	plant metabolite
4,5-dihydroxy-4,5-dihydrobenzo(a)pyrene 4,5-dihydroxy-4,5-dihydrobenzo(a)pyrene: RN given refers to cpd without isomeric designation	1.96	1	0
4-ethynylbiphenyl 4-ethynylbiphenyl: structure given in first source	3.12	1	0
zidovudine Zidovudine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.. zidovudine : A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.	3.1	1	0	azide; pyrimidine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; HIV-1 reverse transcriptase inhibitor
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.	8.48	8	0	aromatic ether; coumarins
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.	2.68	3	0	dichlorobenzene; tetrachlorobiphenyl
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	3.12	1	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).	2.44	2	0	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
6-hydroxybenzo(a)pyrene 6-hydroxybenzo(a)pyrene: RN given refers to parent cpd; structure in first source	3.1	1	0	ortho- and peri-fused polycyclic arene
2,4,5,2',4',5'-hexachlorobiphenyl [no description available]	3.12	5	0	hexachlorobiphenyl
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.	2.01	1	0	dichlorobenzene; tetrachlorobiphenyl
halofantrine halofantrine: used in treatment of mild to moderate acute malaria	2	1	0	phenanthrenes
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.	2.02	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	1.95	1	0	carbopolycyclic compound
ticrynafen Ticrynafen: A novel diuretic with uricosuric action. It has been proposed as an antihypertensive agent.. tienilic acid : An aromatic ketone that is 2,3-dichlorophenoxyacetic acid in which the hydrogen at position 4 on the benzene ring is replaced by a thiophenecarbonyl group. A loop diuretic used to treat hypertension, it was withdrawn from the market in 1982 due to links with hepatitis.	3.12	1	0	aromatic ether; aromatic ketone; dichlorobenzene; monocarboxylic acid; thiophenes	antihypertensive agent; hepatotoxic agent; loop diuretic
1,8-dinitropyrene [no description available]	1.99	1	0	pyrenes
diltiazem Diltiazem: A benzothiazepine derivative with vasodilating action due to its antagonism of the actions of CALCIUM ion on membrane functions.. diltiazem : A 5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate in which both stereocentres have S configuration. A calcium-channel blocker and vasodilator, it is used as the hydrochloride in the management of angina pectoris and hypertension.	3.12	1	0	5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate	antihypertensive agent; calcium channel blocker; vasodilator agent
n-acetyl-4-benzoquinoneimine N-acetyl-4-benzoquinoneimine: reactive arylating intermediate from acetaminophen & N-hydroxyacetaminophen; structure given in first source	1.99	1	0	ketoimine; quinone imine
ng-nitroarginine methyl ester NG-Nitroarginine Methyl Ester: A non-selective inhibitor of nitric oxide synthase. It has been used experimentally to induce hypertension.	2.42	2	0	alpha-amino acid ester; L-arginine derivative; methyl ester; N-nitro compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor
dexibuprofen dexibuprofen: structure in first source	3.1	1	0	ibuprofen	non-narcotic analgesic; non-steroidal anti-inflammatory drug
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	2.39	2	0	polychlorinated dibenzofuran
benoxaprofen benoxaprofen: RN given refers to parent cpd; structure. benoxaprofen : A monocarboxylic acid that is propionic acid substituted at position 2 by a 2-(4-chlorophenyl)-1,3-benzoxazol-5-yl group. It was used as a non-steroidal anti-inflammatory drug until 1982 when it was withdrawn from the market due to adverse side-effects including liver necrosis, photosensitivity, and carcinogenicity in animals.	3.1	1	0	1,3-benzoxazoles; monocarboxylic acid; monochlorobenzenes	antipsoriatic; antipyretic; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; hepatotoxic agent; nephrotoxin; non-narcotic analgesic; non-steroidal anti-inflammatory drug; protein kinase C agonist
chlorodiphenyl (54% chlorine) Chlorodiphenyl (54% Chlorine): A mixture of polychlorinated biphenyls that induces hepatic microsomal UDP-glucuronyl transferase activity towards thyroxine.. Aroclor 1254 : A mixture of polychlorobiphenyls of unspecified composition, containing 54% chlorine (X = Cl or H).	3.22	6	0
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid [no description available]	2.07	1	0	chromanol; monocarboxylic acid; phenols	antioxidant; ferroptosis inhibitor; neuroprotective agent; radical scavenger; Wnt signalling inhibitor
diisopropanolnitrosamine diisopropanolnitrosamine: experimental carcinogen. N,N-bis(2-hydroxypropyl)nitrosamine : A nitrosamine that is dipropylamine in which the hydrogen attached to the nitrogen has been replaced by a nitroso group. It is a genotoxic carcinogen, targeting the lung, liver, thyroid, and kidney.	1.96	1	0	diol; nitrosamine; secondary alcohol	carcinogenic agent
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.	3.49	8	0	epoxide	intercalator
sufentanil Sufentanil: An opioid analgesic that is used as an adjunct in anesthesia, in balanced anesthesia, and as a primary anesthetic agent.. sufentanil : An anilide resulting from the formal condensation of the aryl amino group of 4-(methoxymethyl)-N-phenyl-1-[2-(2-thienyl)ethyl]piperidin-4-amine with propanoic acid.	1.99	1	0	anilide; ether; piperidines; thiophenes	anaesthesia adjuvant; intravenous anaesthetic; mu-opioid receptor agonist; opioid analgesic
2-hydroxybenzo(a)pyrene 2-hydroxybenzo(a)pyrene: RN given refers to parent cpd; structure in first source	3.1	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	1.98	1	0	polychlorinated dibenzofuran
nitrosobis(2-oxopropyl)amine nitrosobis(2-oxopropyl)amine: structure. nitrosobis(2-oxopropyl)amine : A nitrosamine that is iminodiacetone that is substituted by a nitroso group at the N-atom. It induces pancreatic ductal adenocarcinomas in Syrian golden hamsters (other rodents are not susceptible).	1.96	1	0	ketone; nitrosamine	carcinogenic agent
paroxetine Paroxetine: A serotonin uptake inhibitor that is effective in the treatment of depression.. paroxetine : A benzodioxole that consists of piperidine bearing 1,3-benzodioxol-5-yloxy)methyl and 4-fluorophenyl substituents at positions 3 and 4 respectively; the (3S,4R)-diastereomer. Highly potent and selective 5-HT uptake inhibitor that binds with high affinity to the serotonin transporter (Ki = 0.05 nM). Ki values are 1.1, 350 and 1100 nM for inhibition of [3H]-5-HT, [3H]-l-NA and [3H]-DA uptake respectively. Displays minimal affinity for alpha1-, alpha2- or beta-adrenoceptors, 5-HT2A, 5-HT1A, D2 or H1 receptors at concentrations below 1000 nM, however displays weak affinity for muscarinic ACh receptors (Ki = 42 nM). Antidepressant and anxiolytic in vivo.	3.12	1	0	aromatic ether; benzodioxoles; organofluorine compound; piperidines	antidepressant; anxiolytic drug; hepatotoxic agent; P450 inhibitor; serotonin uptake inhibitor
4-(n-methyl-n-nitrosamino)-1-(3-pyridyl)-1-butanone 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone: structure; from tobacco smoke	2.38	2	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.	3.12	1	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.	2	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
alfentanil Alfentanil: A short-acting opioid anesthetic and analgesic derivative of FENTANYL. It produces an early peak analgesic effect and fast recovery of consciousness. Alfentanil is effective as an anesthetic during surgery, for supplementation of analgesia during surgical procedures, and as an analgesic for critically ill patients.. alfentanil : A member of the class of piperidines that is piperidine having a 2-(4-ethyl-5-oxo-4,5-dihydro-1H-tetrazol-1-yl)ethyl group at the 1-position as well as N-phenylpropanamido- and methoxymethyl groups at the 4-position.	3.49	2	0	monocarboxylic acid amide; piperidines	central nervous system depressant; intravenous anaesthetic; mu-opioid receptor agonist; opioid analgesic; peripheral nervous system drug
lovastatin Lovastatin: A fungal metabolite isolated from cultures of Aspergillus terreus. The compound is a potent anticholesteremic agent. It inhibits 3-hydroxy-3-methylglutaryl coenzyme A reductase (HYDROXYMETHYLGLUTARYL COA REDUCTASES), which is the rate-limiting enzyme in cholesterol biosynthesis. It also stimulates the production of low-density lipoprotein receptors in the liver.. lovastatin : A fatty acid ester that is mevastatin carrying an additional methyl group on the carbobicyclic skeleton. It is used in as an anticholesteremic drug and has been found in fungal species such as Aspergillus terreus and Pleurotus ostreatus (oyster mushroom).	2.25	1	0	delta-lactone; fatty acid ester; hexahydronaphthalenes; polyketide; statin (naturally occurring)	anticholesteremic drug; antineoplastic agent; Aspergillus metabolite; prodrug
2-amino-3-methylimidazo(4,5-f)quinoline 2-amino-3-methylimidazo(4,5-f)quinoline: mutagen found in broiled food; RN given refers to parent cpd; structure given in first source; frequently abbreviated as IQ in the literature. 3-methyl-3H-imidazo[4,5-f]quinolin-2-amine : An imidazoquinoline that is 3H-imidazo[4,5-f]quinoline substituted by a methyl group at position 3 and an amino group at position 2.	2.38	2	0	imidazoquinoline	carcinogenic agent
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.	3.12	1	0	3-oxo-Delta(4) steroid; acetylenic compound; tertiary amino compound	abortifacient; contraceptive drug; hormone antagonist; synthetic oral contraceptive
fadrozole Fadrozole: A selective aromatase inhibitor effective in the treatment of estrogen-dependent disease including breast cancer.	3.5	2	0	imidazopyridine
aromasil [no description available]	2.41	1	0	17-oxo steroid; 3-oxo-Delta(1),Delta(4)-steroid	antineoplastic agent; EC 1.14.14.14 (aromatase) inhibitor; environmental contaminant; xenobiotic
zileuton [no description available]	3.12	1	0	1-benzothiophenes; ureas	anti-asthmatic drug; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; ferroptosis inhibitor; leukotriene antagonist; non-steroidal anti-inflammatory drug
clopidogrel Clopidogrel: A ticlopidine analog and platelet purinergic P2Y receptor antagonist that inhibits adenosine diphosphate-mediated PLATELET AGGREGATION. It is used to prevent THROMBOEMBOLISM in patients with ARTERIAL OCCLUSIVE DISEASES; MYOCARDIAL INFARCTION; STROKE; or ATRIAL FIBRILLATION.. clopidogrel : A thienopyridine that is 4,5,6,7-tetrahydrothieno[3,2-c]pyridine in which the hydrogen attached to the nitrogen is replaced by an o-chlorobenzyl group, the methylene hydrogen of which is replaced by a methoxycarbonyl group (the S enantiomer). A P2Y12 receptor antagonist, it is used to inhibit blood clots and prevent heart attacks.	3.12	1	0	methyl ester; monochlorobenzenes; thienopyridine	anticoagulant; P2Y12 receptor antagonist; platelet aggregation inhibitor
liarozole liarozole: inhibits all-trans-retinoic acid 4-hydroxylase; effective against hormone-dependent and hormone-independent tumors; R 75251 is chlorohydrate of R 61405; a potent inhibitor of retinoic acid metabolism; USAN name - liarozole fumarate	2.05	1	0	benzimidazoles
mibefradil Mibefradil: A benzimidazoyl-substituted tetraline that selectively binds and inhibits CALCIUM CHANNELS, T-TYPE.	3.85	3	0	tetralins	T-type calcium channel blocker
gemcitabine gemcitabine : A 2'-deoxycytidine having geminal fluoro substituents in the 2'-position. An inhibitor of ribonucleotide reductase, gemcitabine is used in the treatment of various carcinomas, particularly non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer.	2.41	1	0	organofluorine compound; pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent; antiviral drug; DNA synthesis inhibitor; EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor; environmental contaminant; immunosuppressive agent; photosensitizing agent; prodrug; radiosensitizing agent; xenobiotic
duloxetine [no description available]	2.5	2	0	duloxetine
irinotecan [no description available]	3.12	1	0	carbamate ester; delta-lactone; N-acylpiperidine; pyranoindolizinoquinoline; ring assembly; tertiary alcohol; tertiary amino compound	antineoplastic agent; apoptosis inducer; EC 5.99.1.2 (DNA topoisomerase) inhibitor; prodrug
zanamivir Zanamivir: A guanido-neuraminic acid that is used to inhibit NEURAMINIDASE.	2.31	1	0	guanidines	antiviral agent; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor
octyl gallate [no description available]	3.1	1	0	gallate ester	food antioxidant; hypoglycemic agent; plant metabolite
4,5'-dimethylangelicin [no description available]	2.11	1	0	furanocoumarin
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	1.98	1	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.	2.41	2	0	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.	1.97	1	0	azobenzenes; bis(azo) compound; naphthols	carcinogenic agent; fluorochrome; histological dye
4-vinylphenol 4-vinylphenol: RN given refers to cpd with locants as specified. 4-hydroxystyrene : A member of the class of phenols that is styrene carrying a hydroxy substituent at position 4.	2.02	1	0	phenols	human urinary metabolite; human xenobiotic metabolite
2-amino-9h-pyrido(2,3-b)indole 2-amino-9H-pyrido(2,3-b)indole: pyrolysis product of soybean globulins; RN given refers to unlabeled cpd; structure	1.97	1	0	pyridoindole
venlafaxine hydrochloride Venlafaxine Hydrochloride: A cyclohexanol and phenylethylamine derivative that functions as a SEROTONIN AND NORADRENALINE REUPTAKE INHIBITOR (SNRI) and is used as an ANTIDEPRESSIVE AGENT.	2.1	1	0	hydrochloride
verapamil hydrochloride verapamil hydrochloride : A racemate comprising equimolar amounts of dexverapamil hydrochloride and (S)-verapamil hydrochloride.	2.1	1	0
4-[1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol [no description available]	3.1	1	0	stilbenoid
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.	4.72	9	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.	3.25	4	0	acetylenic compound; benzoxazine; cyclopropanes; organochlorine compound; organofluorine compound	antiviral drug; HIV-1 reverse transcriptase inhibitor
nelfinavir Nelfinavir: A potent HIV protease inhibitor. It is used in combination with other antiviral drugs in the treatment of HIV in both adults and children.. nelfinavir : An aryl sulfide that is used (as its mesylate salt) for treatment of HIV and also exhibits some anticancer properties.	3.12	1	0	aryl sulfide; benzamides; organic heterobicyclic compound; phenols; secondary alcohol; tertiary amino compound	antineoplastic agent; HIV protease inhibitor
2',7'-dichlorofluorescein 2',7'-dichlorofluorescein: RN given refers to parent cpd	3.1	1	0	2-benzofurans	fluorochrome
amprenavir [no description available]	3.12	1	0	carbamate ester; sulfonamide; tetrahydrofuryl ester	antiviral drug; HIV protease inhibitor
diacetylfluorescein [no description available]	1.98	1	0
epigallocatechin gallate epigallocatechin gallate: a steroid 5alpha-reductase inhibitor and antimutagen in green tea (Camellia sinensis). (-)-epigallocatechin 3-gallate : A gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (-)-epigallocatechin.	2.07	1	0	flavans; gallate ester; polyphenol	antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite
6-sulfatoxymelatonin 6-sulfatoxymelatonin: metabolite of melatonin; RN given refers to parent cpd	2	1	0	acetamides
nile red nile red : An organic heterotetracyclic compound that is 5H-benzo[a]phenoxazin-5-one substituted at position 9 by a diethylamino group.	2.08	1	0	aromatic amine; cyclic ketone; organic heterotetracyclic compound; tertiary amino compound	fluorochrome; histological dye
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.	1.97	1	0	methylguanine	mutagen
pyrrolidine dithiocarbamate pyrrolidine dithiocarbamic acid: spelled pyrolidine in J Nutr 1979 reference; RN given refers to parent cpd. pyrrolidine dithiocarbamate : A member of the class of dithiocarbamic acids that is the N-dithiocarboxy derivative of pyrrolidine.	2	1	0	dithiocarbamic acids; pyrrolidines	anticonvulsant; antineoplastic agent; geroprotector; neuroprotective agent; NF-kappaB inhibitor; radical scavenger
16-hydroxytestosterone 16-hydroxytestosterone: RN given refers to (16alpha,17beta)-isomer. 16alpha-hydroxytestosterone : A C19-steroid that is testosterone in which the hydrogen at the 16alpha position has been replaced by a hydroxy group.	3.1	1	0	16alpha-hydroxy steroid; 17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; androstanoid; C19-steroid; diol; secondary alcohol	androgen
rutecarpine rutacarpine: from Evodia rutaecarpa; an ingredient in zhuyu hewei zhitong capsules	4.08	2	0	beta-carbolines
dexverapamil dexverapamil : A 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile that has R configuration. It competitively inhibits the multidrug resistance efflux pump P-glycoprotein (MDR-1, EC 3.6.3.44), thereby potentially increasing the effectiveness of a wide range of antineoplastic drugs which are inactivated by MDR-1 mechanisms. Dexverapamil exhibits lower calcium antagonistic activity and toxicity than racemic verapamil.	3.12	1	0	2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile	EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor
2-methoxyestradiol 2-methoxy-17beta-estradiol : A 17beta-hydroxy steroid, being 17beta-estradiol methoxylated at C-2.	4.37	3	0	17beta-hydroxy steroid; 3-hydroxy steroid	angiogenesis modulating agent; antimitotic; antineoplastic agent; human metabolite; metabolite; mouse metabolite
6-ketoestradiol [no description available]	2.13	1	0
2-methylestradiol 2-methylestradiol: RN given refers to (17beta)-isomer	2.13	1	0
naphthalimides Naphthalimides: Compounds with three fused rings that appear like a naphthalene fused to piperidone or like a benz(de)isoquinoline-1,3-dione (not to be confused with BENZYLISOQUINOLINES which have a methyl separating the naphthyl from the benzyl rings). Members are CYTOTOXINS.	2.04	1	0
2-fluoroestradiol 2-fluoroestradiol: in contrast to 4-fluoroestradiol above cpd is not a carcinogen	2.13	1	0
4,7-phenanthroline [no description available]	1.99	1	0	phenanthroline
1,7-phenanthroline [no description available]	2.41	2	0	phenanthroline
triazoles Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.	3.4	7	0	1,2,3-triazole
isopimpinellin isopimpinellin: from Ruta graveolens & Heracleum lanatum; structure	3.66	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.	3.25	1	0	psoralens	EC 3.1.1.7 (acetylcholinesterase) inhibitor; metabolite
4-chromanone [no description available]	1.99	1	0	chromones
5-hydroxyflavone [no description available]	4.23	5	0	flavones
5,6,7,8-tetrahydro-1-naphthol 5,6,7,8-tetrahydro-1-naphthol : 1-naphthol hydrogenated at C-5, -6, -7 and -8.	3.1	1	0	tetralins
alfatradiol alfatradiol: used for treating androgenetic alopecia. 17alpha-estradiol : An estradiol that is estra-1,3,5(10)-triene substituted by hydroxy groups at positions 3 and 17 (the 17alpha stereoisomer).	3.1	1	0	17alpha-hydroxy steroid; 3-hydroxy steroid; estradiol	estrogen; geroprotector
4-methoxyestradiol 4-methoxyestradiol: RN given refers to (17beta)-isomer. 4-methoxy-17beta-estradiol : A 17beta-hydroxy steroid that is 17beta-estradiol in which the hydrogen at position 4 has been replaced by a methoxy group.	3.25	1	0	17beta-hydroxy steroid; 3-hydroxy steroid; aromatic ether; phenols	estrogen; human metabolite; rat metabolite
talinolol [no description available]	2.17	1	0	ureas
4-hydroxyquinoline 4-quinolone : A quinolone that is 1,4-dihydroquinoline substituted by an oxo group at position 4.	3.1	1	0	monohydroxyquinoline; quinolone
resorufin [no description available]	2.92	4	0	phenoxazine
4(5)-phenylimidazole 4(5)-phenylimidazole: tautomeric cpd; cytochrome P450 14alpha-sterol demethylase, CYP51 antagonist	1.96	1	0
3,5-dicarbethoxy-2,6-dimethyl-4-ethyl-1,4-dihydropyridine 3,5-dicarbethoxy-2,6-dimethyl-4-ethyl-1,4-dihydropyridine: causes NADPH-& time-dependent in vitro loss of hepatic microsomal cytochrome P-450; do not confuse with etoprine, also called DDEP	3.51	2	0
dipropylacetamide dipropylacetamide: structure. valpromide : A fatty amide derived from valproic acid.	1.98	1	0	fatty amide	geroprotector; metabolite; teratogenic agent
enrofloxacin Enrofloxacin: A fluoroquinolone antibacterial and antimycoplasma agent that is used in veterinary practice.. enrofloxacin : A quinolinemonocarboxylic acid that is 1,4-dihydroquinoline-3-carboxylic acid substituted by an oxo group at position 4, a fluoro group at position 6, a cyclopropyl group at position 1 and a 4-ethylpiperazin-1-yl group at position 7. It is a veterinary antibacterial agent used for the treatment of pets.	2.13	1	0	cyclopropanes; N-alkylpiperazine; N-arylpiperazine; organofluorine compound; quinolinemonocarboxylic acid; quinolone	antibacterial agent; antimicrobial agent; antineoplastic agent
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.	1.98	1	0	nordihydroguaiaretic acid	antineoplastic agent; hypoglycemic agent; lipoxygenase inhibitor; metabolite
voriconazole Voriconazole: A triazole antifungal agent that specifically inhibits STEROL 14-ALPHA-DEMETHYLASE and CYTOCHROME P-450 CYP3A.. voriconazole : A triazole-based antifungal agent used for the treatment of esophageal candidiasis, invasive pulmonary aspergillosis, and serious fungal infections caused by Scedosporium apiospermum and Fusarium spp. It is an inhibitor of cytochrome P450 2C9 (CYP2C9) and CYP3A4.	2.9	3	0	conazole antifungal drug; difluorobenzene; pyrimidines; tertiary alcohol; triazole antifungal drug	P450 inhibitor
bufuralol bufuralol: RN given refers to cpd without isomeric designation; structure	2.39	2	0	benzofurans
oleandomycin [no description available]	2.06	1	0	oleandomycins
berberrubine berberrubine: RN refers to chloride salt; a protoberberine alkaloid antitumor agent which exhibits topoisomerase II poison activity as well as catalytic inhibition activity; structure in first source	2.11	1	0
dehydroleucodine dehydroleucodine: has antimicrobial activity; RN given refers to (3aS-(3aalpha,9aalpha,9bbeta))-isomer	2.05	1	0
homoeriodictyol homoeriodictyol: structure in first source. homoeriodictyol : A trihydroxyflavanone that consists of 3'-methoxyflavanone in which the three hydroxy substituents are located at positions 4', 5, and 7.	4.09	2	0	3'-methoxyflavanones; 4'-hydroxyflavanones; monomethoxyflavanone; trihydroxyflavanone	flavouring agent; metabolite
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
5-phenyl-1-pentyne [no description available]	3.52	2	0
3-methylflavone-8-carboxylic acid 3-methylflavone-8-carboxylic acid: metabolite of flavoxate; RN in Chemline for the Na salt: 58348-97-3. 3-methylflavone-8-carboxylic acid : A member of the class of flavones that is flavone substituted at position 3 by a methyl group and at position 8 by a carboxylic acid group.	2.06	1	0	flavones; oxo monocarboxylic acid	EC 3.1.4.* (phosphoric diester hydrolase) inhibitor
1-benzylimidazole 1-benzylimidazole: inhibits human thromboxane synthetase	2.01	1	0
5,7,4'-trimethylapigenin 5,7,4'-trimethylapigenin: a flavonoid from the East Asian medicinal plant Orthosiphon spicatus; prevents oxidative inactivation of 15-lipoxygenase; structure given in first source	2.06	1	0	ether; flavonoids
cyclopropanecarboxamide cyclopropylcarboxamide : Carboxamides RC(=O)NR'R'' where R is a cyclopropyl group.	2.25	1	0	cyclopropylcarboxamide
1-phenylimidazole 1-phenylimidazole: ligand for cytochrome P-450 & inhibitor of microsomal oxidation	1.97	1	0
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.	3.12	1	0	macrolide antibiotic	antibacterial drug; environmental contaminant; protein synthesis inhibitor; xenobiotic
5,7-dimethoxyflavone chrysin 5,7-dimethyl ether : A dimethoxyflavone that is the 5,7-dimethyl ether derivative of chrysin.	2.02	1	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.	3.12	1	0	3-(1-methylpyrrolidin-2-yl)pyridine	anxiolytic drug; biomarker; immunomodulator; mitogen; neurotoxin; nicotinic acetylcholine receptor agonist; peripheral nervous system drug; phytogenic insecticide; plant metabolite; psychotropic drug; teratogenic agent; xenobiotic
2-acetylbenzothiophene 2-acetylbenzothiophene: metabolite of zileuton; structure in first source	2.25	1	0
17-alpha-hydroxypregnenolone 17-alpha-Hydroxypregnenolone: A 21-carbon steroid that is converted from PREGNENOLONE by STEROID 17-ALPHA-HYDROXYLASE. It is an intermediate in the delta-5 pathway of biosynthesis of GONADAL STEROID HORMONES and the adrenal CORTICOSTEROIDS.. 17alpha-hydroxypregnenolone : A hydroxypregnenolone carrying an alpha-hydroxy group at position 17.	3.1	1	0	17alpha-hydroxy-C21-steroid; 17alpha-hydroxy steroid; 3beta-hydroxy-Delta(5)-steroid; hydroxypregnenolone; tertiary alpha-hydroxy ketone	human metabolite; mouse metabolite
methylglucoside [no description available]	2.02	1	0
5-(3-hydroxyphenyl)-5-phenylhydantoin 5-(3-hydroxyphenyl)-5-phenylhydantoin: metabolite of phenytoin; RN given refers to cpd without isomeric designation	3.1	1	0
7-amino-4-methylcoumarin 7-amino-4-methylcoumarin: RN given refers to parent cpd	3.1	1	0	7-aminocoumarins	fluorochrome
lekoptin (S)-verapamil : A 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile that has S configuration.	3.12	1	0	2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile
lopinavir [no description available]	3.12	1	0	amphetamines; dicarboxylic acid diamide	anticoronaviral agent; antiviral drug; HIV protease inhibitor
11-hydroxyprogesterone, (11alpha)-isomer 11alpha-hydroxyprogesterone : A 11alpha-hydroxy steroid that is pregn-4-ene-3,20-dione substituted by a hydroxy group at position 11.	3.1	1	0	11alpha-hydroxy steroid; 20-oxo steroid; 3-oxo-Delta(4) steroid
brexanolone brexanolone: a mixture of allopregnanolone and sulfobutylether‐beta‐cyclodextrin for treatment of postpartum depression. brexanolone : A 3-hydroxy-5alpha-pregnan-20-one in which the hydroxy group at position 3 has alpha-configuration. It is a metabolite of the sex hormone progesterone and used for the treatment of postpartum depression in women.	3.1	1	0	3-hydroxy-5alpha-pregnan-20-one	antidepressant; GABA modulator; human metabolite; intravenous anaesthetic; sedative
3,5-diiodothyronine, (l)-isomer [no description available]	3.1	1	0	phenylalanine derivative
estrone 3-methyl ether estrone 3-methyl ether: RN given refers to cpd with unspecified isomeric designation; structure	2.13	1	0
2-(3,4-dimethoxyphenyl)-5-amino-2-isopropylvaleronitrile 2-(3,4-dimethoxyphenyl)-5-amino-2-isopropylvaleronitrile: structure in first source. D617 : A nitrile that is pentanenitrile substituted by a 3,4-dimethoxyphenyl group at position 2, a methylamino group at position 4 and an isopropyl group at position 2. It is a metabolite of the drug verapamil.	3.12	1	0	dimethoxybenzene; nitrile; secondary amino compound	drug metabolite; marine xenobiotic metabolite
harmol hydrochloride [no description available]	3.1	1	0
5-Methoxyflavone 5-methoxyflavone: DNA polymerase-beta inhibitor and neuroprotective agent against beta-amyloid toxicity; structure in first source	2.06	1	0	ether; flavonoids
4',5,6,7-tetramethoxyflavone 4',5,6,7-tetramethoxyflavone: structure given in first source; from plant Eupatorium odoratum. 4',5,6,7-tetramethoxyflavone : A tetramethoxyflavone that is the tetra-O-methyl derivative of scutellarein.	1.99	1	0	tetramethoxyflavone	antimutagen; plant metabolite
eupatorin eupatorin: a flavonoid from the East Asian medicinal plant Orthosiphon spicatus; prevents oxidative inactivation of 15-lipoxygenase; structure given in first source. eupatorin : A trimethoxyflavone that is 6-hydroxyluteolin in which the phenolic hydogens at positions 4', 6 and 7 have been replaced by methyl groups.	3.25	1	0	dihydroxyflavone; polyphenol; trimethoxyflavone	anti-inflammatory agent; antineoplastic agent; apoptosis inducer; Brassica napus metabolite; calcium channel blocker; P450 inhibitor; vasodilator agent
3,5,7,3',4'-pentamethoxyflavone 3,5,7,3',4'-pentamethoxyflavone: causes relaxation of cavernosum; structure in first source	2.08	1	0
phellopterin phellopterin: a naturally occurring furanocoumarin found in roots of Angelica dahurica; structure in first source	2.17	1	0	psoralens
diosgenin [no description available]	3.1	1	0	3beta-sterol; hexacyclic triterpenoid; sapogenin; spiroketal	antineoplastic agent; antiviral agent; apoptosis inducer; metabolite
sarsasapogenin, (3beta,5alpha,25r)-isomer tigogenin : A widely used steroidal sapogenin isolated from several plant species and used for synthesizing steroid drugs.	3.1	1	0	sapogenin	gout suppressant; plant metabolite
benzyl selenocyanate benzyl selenocyanate: prevents colon carcinogenesis	3.25	1	0
3 alpha,17 alpha-dihydroxy-5 beta-pregnan-20-one 3alpha,17alpha-dihydroxy-5beta-pregnan-20-one : A 17alpha-hydroxy steroid that is 3alpha-hydroxy-5beta-pregnan-20-one carrying an additional hydroxy group at position 17alpha.	3.1	1	0	17alpha-hydroxy steroid; 20-oxo steroid; 3alpha-hydroxy steroid; C21-steroid; corticosteroid hormone	human urinary metabolite
2-methoxyestriol [no description available]	3.1	1	0
cobalt Cobalt: A trace element that is a component of vitamin B12. It has the atomic symbol Co, atomic number 27, and atomic weight 58.93. It is used in nuclear weapons, alloys, and pigments. Deficiency in animals leads to anemia; its excess in humans can lead to erythrocytosis.. cobalt(1+) : A monovalent inorganic cation obtained from cobalt.. cobalt atom : A cobalt group element atom that has atomic number 27.	2.65	3	0	cobalt group element atom; metal allergen	micronutrient
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.	3.13	5	0	17beta-hydroxy steroid; 3-hydroxy steroid; organofluorine compound; sulfoxide	antineoplastic agent; estrogen antagonist; estrogen receptor antagonist
aflatoxicol aflatoxicol: metabolite of aflatoxin B; RN given refers to (1S-(1alpha,6beta,9abeta))-isomer; structure	1.98	1	0
aflatoxin q1 aflatoxin Q1 : A member of the class of aflatoxins that is aflatoxin B1 in which the hydrogen at the pro-3S position is replaced by a hydroxy group.	1.98	1	0	aflatoxin; aromatic ether; aromatic ketone	carcinogenic agent; human xenobiotic metabolite
desethylamiodarone desethylamiodarone: metabolite of amiodarone; structure given in first source	2.45	2	0	aromatic ketone
sn 38 SN-38 : A member of the class of pyranoindolizinoquinolines that is (4S)-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione bearing two additional ethyl substituents at positions 4 and 11 as well as two additional hydroxy substituents at positions 4 and 9. It is the active metabolite of irinotecan and is ~1000 times more active than irinotecan itself.	3.12	1	0	delta-lactone; phenols; pyranoindolizinoquinoline; tertiary alcohol	antineoplastic agent; apoptosis inducer; drug metabolite; EC 5.99.1.2 (DNA topoisomerase) inhibitor
bosentan anhydrous Bosentan: A sulfonamide and pyrimidine derivative that acts as a dual endothelin receptor antagonist used to manage PULMONARY HYPERTENSION and SYSTEMIC SCLEROSIS.	1.99	1	0	primary alcohol; pyrimidines; sulfonamide	antihypertensive agent; endothelin receptor antagonist
androsta-1,4,6-triene-3,17-dione androsta-1,4,6-triene-3,17-dione: blocks aromatization of testosterone to estradiol; aromatase antagonist. androsta-1,4,6-triene-3,17-dione : An androstanoid that is androsta-1,4,6-triene substituted by oxo groups at positions 3 and 17.	3.07	1	0	17-oxo steroid; 3-oxo-Delta(1),Delta(4)-steroid; androstanoid	EC 1.14.14.14 (aromatase) inhibitor; human xenobiotic metabolite
n-nitrosomethyl-2-oxopropylamine N-nitrosomethyl-2-oxopropylamine: RN & N1 from 9th CI Form Index; structure in first source	1.96	1	0
diacetyldichlorofluorescein diacetyldichlorofluorescein: stable storage form of dichlorofluorescein	2.03	1	0
vanoxerine vanoxerine dihydrochloride : A hydrochloride salt that is obtained by reaction of vanoxerine with two equivalents of hydrogen chloride. Potent, competitive inhibitor of dopamine uptake (Ki = 1 nM for inhibition of striatal dopamine uptake). Has > 100-fold lower affinity for the noradrenalin and 5-HT uptake carriers. Also a potent sigma ligand (IC50 = 48 nM). Centrally active following systemic administration.	2.1	1	0	hydrochloride	dopamine uptake inhibitor
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.	3.1	1	0	hydroxylamine; imidazopyridine	carcinogenic agent; genotoxin; human xenobiotic metabolite; mouse metabolite; mutagen; neurotoxin; rat metabolite
norverapamil norverapamil: N-demethylated active metabolite of verapamil; RN given refers to parent cpd without isomeric designation; structure in second source. norverapamil : A racemate comprising equimolar amounts of (R)- and (S)-norverapamil. The major active metabolite of verapamil.. 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl]amino}-2-(propan-2-yl)pentanenitrile : A secondary amino compound that is 3,4-dimethoxyphenylethylamine in which one of the hydrogens attached to the nitrogen has been replaced by a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.	3.12	1	0	aromatic ether; nitrile; polyether; secondary amino compound
pentoxyresorufin [no description available]	1.99	1	0
3-methylsulfonyl-4,5,3',4'-tetrachlorobiphenyl [no description available]	2.89	4	0
n-monodemethyldiltiazem N-monodemethyldiltiazem: RN given refers to (cis)-isomer; structure given in first source	3.12	1	0	benzothiazepine
1-hydroxymethylmidazolam 1-hydroxymethylmidazolam: metabolite of midazolam. 1-hydroxymidazolam : An imidazobenzodiazepine that is midazolam in which one of the hydrogens of the methyl group is substituted by a hydroxy group. It is the major metabolite of the anesthetic, midazolam.	2.02	1	0	aromatic primary alcohol; imidazobenzodiazepine; monofluorobenzenes; organochlorine compound	drug metabolite; human blood serum metabolite; human urinary metabolite
(S)-Mephenytoin [no description available]	2.06	1	0	imidazolidine-2,4-dione
ecopipam ecopipam: structure given in first source	3.1	1	0	benzazepine
sphondin sphondin: from Heracleum laciniatum; cause of phototoxicity in patient with vitiligo	2.17	1	0	furanocoumarin
exp3174 losartan carboxylic acid: structure given in first source. losartan carboxylic acid : A biphenylyltetrazole that is losartan with the hydroxymethyl group at position 5 on the imidazole ring replaced with a carboxylic acid.	1.98	1	0	biphenylyltetrazole; imidazoles; organochlorine compound	metabolite
2,3-bis(3'-hydroxybenzyl)butyrolactone 2,3-bis(3'-hydroxybenzyl)butyrolactone: lignan isolated from urine of humans & other mammals; RN given refers to cpd without isomeric designation; structure given in second source	2.05	1	0	lignan
liquiritigenin liquiritigenin: structure given in first source; isolated from Pterocarpus marsupium. 4',7-dihydroxyflavanone : A dihydroxyflavanone in which the two hydroxy substituents are located at positions 4' and 7.. liquiritigenin : A dihydroxyflavanone compound having the two hydroxy substituents at the 4'- and 7-positions. Isolated from the root of Glycyrrhizae uralensis, it is a selective agonist for oestrogen receptor beta.	2.04	1	0	4',7-dihydroxyflavanone	hormone agonist; plant metabolite
phenoxazinone [no description available]	2.37	2	0
ibuprofen, (r)-isomer [no description available]	3.1	1	0	ibuprofen
6-methyl-1,3,8-trichlorodibenzofuran 6-methyl-1,3,8-trichlorodibenzofuran: structure given in first source	8.8	3	0
11-hydroxytestosterone 11-hydroxytestosterone: RN given refers to (11 beta,17 beta)-isomer. 11beta-hydroxytestosterone : An androstanoid that is testosterone carrying an additional hydroxy substituent at the 11beta-position.	3.1	1	0	11beta-hydroxy steroid; 17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; androstanoid; C19-steroid	bacterial xenobiotic metabolite; human xenobiotic metabolite; marine metabolite
protoberberine protoberberine: a benzyltetrahydroisoquinoline derivative that appears as an isoquinoline annelated (adjoined) with a naphthylene; the nitrogen is typically quarternary; nitidine is annelated differently; RN given refers to parent cpd	2.11	1	0
norbuprenorphine norbuprenorphine: metabolite of buprenorphine found in urine & feces; RN given refers to (5alpha,7alpha)-isomer; structure given in first source	3.1	1	0	phenanthrenes
benzyloxyresorufin [no description available]	2	1	0
2-ethynylnaphthalene 2-ethynylnaphthalene: RN given refers to unlabeled parent cpd	3.12	1	0
7-methoxyresorufin [no description available]	1.99	1	0
benzo(a)pyrene-3,6-quinol [no description available]	3.1	1	0
dl 111-it 3-(2-ethylphenyl)-5-(3-methoxyphenyl)-1H-1,2,4-triazole: non-hormonal antifertility agent; RN & N1 from CA Vol 90	2.02	1	0
n-(4-(7-diethylamino-4-methylcoumarin-3-yl)phenyl)maleimide N-(4-(7-diethylamino-4-methylcoumarin-3-yl)phenyl)maleimide: structure given in first source. 7-diethylamino-3-(4-maleimidophenyl)-4-methylcoumarin : A member of the class of coumarins that is 2H-chromen-2-one substituted by 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)phenyl, methyl, and diethylamino groups at positions 3, 4 and 7, respectively. It is a thiol-reactive fluorescent dye.	2.03	1	0	benzenes; coumarins; maleimides; tertiary amino compound	fluorescent dye
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).	3.12	1	0	nitrogen oxoacid
glabridin [no description available]	3.12	1	0	hydroxyisoflavans	antiplasmodial drug
3-(2-(2,4,6-trimethylphenyl)thioethyl)-4-methylsydnone 3-(2-(2,4,6-trimethylphenyl)thioethyl)-4-methylsydnone: porphyrinogenic agent; structure given in first source	3.51	2	0
4-hydroxymidazolam 4-hydroxymidazolam: metabolite of midazolam; structure given in first source. 4-hydroxymidazolam : An imidazobenzodiazepine that is midazolam which is substituted by a hydroxy group at position 4. It is the minor hydroxylated metabolite of the anesthetic, midazolam.	2.02	1	0	imidazobenzodiazepine; monofluorobenzenes; organic hydroxy compound; organochlorine compound	drug metabolite; human blood serum metabolite; human urinary metabolite
furamidine furamidine: RN given refers to parent cpd; WR 199385 refers to di-HCl; pafuramidine is a prodrug of this	2.43	2	0
estrone-3-o-sulfamate estrone-3-O-sulfamate: a steroid sulfatase inhibitor	2.13	1	0
7-ethoxy-4-trifluoromethylcoumarin [no description available]	1.99	1	0
2-(4-morpholinyl)-4h-1-benzopyran-4-one 2-(4-morpholinyl)-4H-1-benzopyran-4-one: an aminochromone; exhibits both antiproliferative and antichemotactic activity in vitro	2.02	1	0
3-methoxy-7h-8-methyl-11-((3'-amino)propylamino)benzo(e)pyrido(4,3-b)indole 3-methoxy-7H-8-methyl-11-((3'-amino)propylamino)benzo(e)pyrido(4,3-b)indole: a benzo(e)pyridoindole derivative	2.02	1	0
omega-n-methylarginine omega-N-Methylarginine: A competitive inhibitor of nitric oxide synthetase.. N(omega)-methyl-L-arginine : A L-arginine derivative with a N(omega)-methyl substituent.	2.07	1	0	amino acid zwitterion; arginine derivative; guanidines; L-arginine derivative; non-proteinogenic L-alpha-amino acid
febuxostat Febuxostat: A thiazole derivative and inhibitor of XANTHINE OXIDASE that is used for the treatment of HYPERURICEMIA in patients with chronic GOUT.. febuxostat : A 1,3-thiazolemonocarboxylic acid that is 4-methyl-1,3-thiazole-5-carboxylic acid which is substituted by a 3-cyano-4-(2-methylpropoxy)phenyl group at position 2. It is an orally-active, potent, and selective xanthine oxidase inhibitor used for the treatment of chronic hyperuricaemia in patients with gout.	2.21	1	0	1,3-thiazolemonocarboxylic acid; aromatic ether; nitrile	EC 1.17.3.2 (xanthine oxidase) inhibitor
3-methoxyflavone 3-methoxyflavone: from Aspergillus niger; structure in first source	2.08	1	0
docetaxel [no description available]	2.11	1	0	hydrate; secondary alpha-hydroxy ketone	antineoplastic agent
docetaxel anhydrous Docetaxel: A semisynthetic analog of PACLITAXEL used in the treatment of locally advanced or metastatic BREAST NEOPLASMS and NON-SMALL CELL LUNG CANCER.. docetaxel anhydrous : A tetracyclic diterpenoid that is paclitaxel with the N-benzyloxycarbonyl group replaced by N-tert-butoxycarbonyl, and the acetoxy group at position 10 replaced by a hydroxy group.	3.02	4	0	secondary alpha-hydroxy ketone; tetracyclic diterpenoid	antimalarial; antineoplastic agent; photosensitizing agent
schisantherin a [no description available]	3.12	1	0	tannin
5-hydroxy-3',4',6,7-tetramethoxyflavone 5-hydroxy-3',4',6,7-tetramethoxyflavone: isolated from Artemisia argyi	2.17	1	0
1-ethynylpyrene 1-ethynylpyrene: RN & structure given in first source; RN not in Chemline 12/84	4.02	4	0
phorbols Phorbols: The parent alcohol of the tumor promoting compounds from CROTON OIL (Croton tiglium).	2.36	2	0	diterpene; terpenoid fundamental parent
naproxen Naproxen: An anti-inflammatory agent with analgesic and antipyretic properties. Both the acid and its sodium salt are used in the treatment of rheumatoid arthritis and other rheumatic or musculoskeletal disorders, dysmenorrhea, and acute gout.. naproxen : A methoxynaphthalene that is 2-methoxynaphthalene substituted by a carboxy ethyl group at position 6. Naproxen is a non-steroidal anti-inflammatory drug commonly used for the reduction of pain, fever, inflammation and stiffness caused by conditions such as osteoarthritis, kidney stones, rheumatoid arthritis, psoriatic arthritis, gout, ankylosing spondylitis, menstrual cramps, tendinitis, bursitis, and for the treatment of primary dysmenorrhea. It works by inhibiting both the COX-1 and COX-2 enzymes.	3.1	1	0	methoxynaphthalene; monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; gout suppressant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
lubazodone hydrochloride lubazodone hydrochloride: structure given in first source	2	1	0
diallyl sulfone diallyl sulfone: metabolite of diallyl sulfide	3.12	1	0
oracine oracine: structure in first source; 11-dihydrooracin is the enantiomer	2	1	0
ly 56110 LY 56110: structure given in first source	3.07	1	0
cortolone [no description available]	3.1	1	0	21-hydroxy steroid
kynurenine L-kynurenine : A kynurenine that has L configuration.	3.35	1	0	amino acid zwitterion; kynurenine; non-proteinogenic L-alpha-amino acid	human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
cannabielsoin cannabielsoin: metabolite of cannabidiol; structure given in first source	1.97	1	0
noralfentanil noralfentanil: metabolite of sufentanil & alfentanil; structure given in first source; RN given refers to unlabeled cpd	3.08	1	0	anilide
4'-hydroxyflavanone 4'-hydroxyflavanone: structure in first source. 4'-hydroxyflavanones : Any hydroxyflavanone having a hydroxy substituent located at position 4'.	1.99	1	0	4'-hydroxyflavanones; monohydroxyflavanone
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).	2.39	2	0	amino acid zwitterion; angiotensin II	human metabolite
ropivacaine Ropivacaine: An anilide used as a long-acting local anesthetic. It has a differential blocking effect on sensory and motor neurons.. ropivacaine : The piperidinecarboxamide obtained by the formal condensation of N-propylpipecolic acid and 2,6-dimethylaniline.. (S)-ropivacaine : A piperidinecarboxamide-based amide-type local anaesthetic (amide caine) in which (S)-N-propylpipecolic acid and 2,6-dimethylaniline are combined to form the amide bond.	1.99	1	0	piperidinecarboxamide; ropivacaine	local anaesthetic
2'-hydroxyflavanone [no description available]	1.99	1	0
l 694,458 DMP 777: structure given in first source	3.12	1	0
limonin [no description available]	3.12	1	0	epoxide; furans; hexacyclic triterpenoid; lactone; limonoid; organic heterohexacyclic compound	inhibitor; metabolite; volatile oil component
9-ethynylphenanthrene 9-ethynylphenanthrene: structure given in first source	3.12	1	0
isoline isoline: a major retronecine-type pyrrolizidine alkaloid from Ligularia duciformis; structure in first source	2.03	1	0
aflatoxin b1 Aflatoxin B1: A potent hepatotoxic and hepatocarcinogenic mycotoxin produced by the Aspergillus flavus group of fungi. It is also mutagenic, teratogenic, and causes immunosuppression in animals. It is found as a contaminant in peanuts, cottonseed meal, corn, and other grains. The mycotoxin requires epoxidation to aflatoxin B1 2,3-oxide for activation. Microsomal monooxygenases biotransform the toxin to the less toxic metabolites aflatoxin M1 and Q1.. aflatoxin B1 : An aflatoxin having a tetrahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h]chromene skeleton with oxygen functionality at positions 1, 4 and 11.	9.06	15	0	aflatoxin; aromatic ether; aromatic ketone	carcinogenic agent; human metabolite
cirsimaritin cirsimaritin: has antagonist or partial agonist activity on benzodiazepine receptors. cirsimaritin : A dimethoxyflavone that is flavone substituted by methoxy groups at positions 6 and 7 and hydroxy groups at positions 5 and 4' respectively.	2.4	2	0	dihydroxyflavone; dimethoxyflavone
dihydrocubebin dihydrocubebin: extract of leaves of Piper guineense Schum. & Thonn.; structure. dihydrocubebin : A glycol that is butane-1,4-diol substituted at the 2- and 3-positions by (1,3-benzodioxol-5-yl)methyl groups (the R,R-configuration).	3.12	1	0	benzodioxoles; butanediols; glycol; lignan
carbocysteine Carbocysteine: A compound formed when iodoacetic acid reacts with sulfhydryl groups in proteins. It has been used as an anti-infective nasal spray with mucolytic and expectorant action.. S-carboxymethyl-L-cysteine : An L-cysteine thioether that is L-cysteine in which the hydrogen of the thiol group has been replaced by a carboxymethyl group.	3.1	1	0	L-cysteine thioether; non-proteinogenic L-alpha-amino acid	mucolytic
etravirine [no description available]	3.4	5	0	aminopyrimidine; aromatic ether; dinitrile; organobromine compound	antiviral agent; HIV-1 reverse transcriptase inhibitor
hydrastine [no description available]	3.12	1	0	isoquinolines	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.	5.23	16	0	acetate ester; epoxide; macrolide antibiotic; monosaccharide derivative; polyketide; semisynthetic derivative	EC 1.14.13.97 (taurochenodeoxycholate 6alpha-hydroxylase) inhibitor; xenobiotic
atorvastatin calcium 2-phenyl-2-(1-piperidinyl)propane: cytochromes P450 2B1 and P450 2B6 antagonist; structure in first source	3.12	1	0
cholic acid Cholic Acid: A major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion.. cholic acid : A bile acid that is 5beta-cholan-24-oic acid bearing three alpha-hydroxy substituents at position 3, 7 and 12.	3.77	3	0	12alpha-hydroxy steroid; 3alpha-hydroxy steroid; 7alpha-hydroxy steroid; bile acid; C24-steroid; trihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
deoxycholic acid Deoxycholic Acid: A bile acid formed by bacterial action from cholate. It is usually conjugated with glycine or taurine. Deoxycholic acid acts as a detergent to solubilize fats for intestinal absorption, is reabsorbed itself, and is used as a choleretic and detergent.. deoxycholic acid : A bile acid that is 5beta-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 12 respectively.	1.97	1	0	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human blood serum metabolite
5 alpha-androstane-3 beta,17 beta-diol 5alpha-androstane-3beta,17beta-diol : An androstane-3,17-diol that is 5alpha-androstane substituted by beta-hydroxy groups at positions 3 and 17. It is a metabolite of dihydrotestosterone.	3.1	1	0	17beta-hydroxy steroid; 3beta-hydroxy steroid; androstane-3,17-diol	Daphnia magna metabolite; human metabolite
cortol [no description available]	3.1	1	0	21-hydroxy steroid
21-hydroxypregnenolone 21-hydroxypregnenolone: RN given refers to (3beta)-isomer;. 21-hydroxypregnenolone : A hydroxypregnenolone that is pregnenolone which has been substituted by a hydroxy group at position 21.	3.1	1	0	21-hydroxy steroid; hydroxypregnenolone; primary alpha-hydroxy ketone	mouse 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.	3.8	3	0	17beta-hydroxy steroid; 2-hydroxy steroid	carcinogenic agent; human metabolite; metabolite; mouse metabolite; prodrug
epietiocholanolone epietiocholanolone : A 3beta-hydroxy steroid that is 5beta-androstane substituted by a hydroxy group at position 3beta and an oxo group at position 17. It is a metabolite of testosterone.	3.1	1	0	17-oxo steroid; 3beta-hydroxy steroid; androstanoid	androgen; animal metabolite; human blood serum metabolite; mouse metabolite; rat metabolite
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	3.39	7	0
withaferin a withaferin A: an antiestrogen and phytogenic antineoplastic agent isolated from leaves of Withania somnifera Dun.; structure. withaferin A : A withanolide that is 5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione substituted by hydroxy groups at positions 4 and 27 (the 4beta,5beta,6beta,22R stereoisomer). Isolated from Physalis longifolia, it exhibits cytotoxic activity.	2.17	1	0	27-hydroxy steroid; 4-hydroxy steroid; delta-lactone; enone; epoxy steroid; ergostanoid; primary alcohol; secondary alcohol; withanolide	antineoplastic agent; apoptosis inducer
3',4'-dimethoxy-alpha-naphthoflavone 3',4'-dimethoxy-alpha-naphthoflavone: activated Ah receptor; structure in first source	4.13	4	0
wortmannin [no description available]	2.02	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
menthofuran menthofuran: RN given refers to cpd without isomeric designation; derives from cyclization of pulegone. menthofuran : A monoterpenoid that is 4,5,6,7-tetrahydro-1-benzofuran substituted by methyl groups at positions 3 and 6.	3.12	1	0	1-benzofurans; monoterpenoid	nematicide; plant metabolite
sakuranetin [no description available]	2.4	2	0
demethyleneberberine demethyleneberberine: structure in first source	3.63	2	0
5,7-dimethoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one [no description available]	2.06	1	0	ether; flavonoids
nsc 674495 NSC 674495: structure in first source	2	1	0
bortezomib [no description available]	2.07	1	0	amino acid amide; L-phenylalanine derivative; pyrazines	antineoplastic agent; antiprotozoal drug; protease inhibitor; proteasome inhibitor
ritonavir Ritonavir: An HIV protease inhibitor that works by interfering with the reproductive cycle of HIV. It also inhibits CYTOCHROME P-450 CYP3A.. ritonavir : An L-valine derivative that is L-valinamide in which alpha-amino group has been acylated by a [(2-isopropyl-1,3-thiazol-4-yl)methyl]methylcarbamoyl group and in which a hydrogen of the carboxamide amino group has been replaced by a (2R,4S,5S)-4-hydroxy-1,6-diphenyl-5-{[(1,3-thiazol-5-ylmethoxy)carbonyl]amino}hexan-2-yl group. A CYP3A inhibitor and antiretroviral drug from the protease inhibitor class used to treat HIV infection and AIDS, it is often used as a fixed-dose combination with another protease inhibitor, lopinavir. Also used in combination with dasabuvir sodium hydrate, ombitasvir and paritaprevir (under the trade name Viekira Pak) for treatment of chronic hepatitis C virus genotype 1 infection as well as cirrhosis of the liver.	3.52	2	0	1,3-thiazoles; carbamate ester; carboxamide; L-valine derivative; ureas	antiviral drug; environmental contaminant; HIV protease inhibitor; xenobiotic
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.	2.42	2	0
naringenin (S)-naringenin : The (S)-enantiomer of naringenin.	4.04	4	0	(2S)-flavan-4-one; naringenin	expectorant; plant metabolite
taxifolin (+)-taxifolin : A taxifolin that has (2R,3R)-configuration.	1.99	1	0	taxifolin	metabolite
2-hydroxyestrone 2-hydroxyestrone: catechol estrogen which is a major metabolite of estradiol in man & animals; RN given refers to parent cpd. 2-hydroxyestrone : A 2-hydroxy steroid that is estrone substituted by a hydroxy group at position 2.	3.1	1	0	2-hydroxy steroid; catechols	human metabolite
2-methoxyestrone 2-methoxyestrone : A 17-oxo steroid that is estrone in which the hydrogen at position 2 has been replaced by a methoxy group.	2.13	1	0	17-oxo steroid; 3-hydroxy steroid; alicyclic ketone; aromatic ether; phenolic steroid; phenols	human metabolite; mouse metabolite
dehydroascorbic acid Dehydroascorbic Acid: The reversibly oxidized form of ascorbic acid. It is the lactone of 2,3-DIKETOGULONIC ACID and has antiscorbutic activity in man on oral ingestion.. L-dehydroascorbate : An organic anion and the conjugate base of L-dehydroascorbic acid, arising from deprotonation of the acidic C2-position.. L-dehydroascorbic acid : Dehydroascorbic acid having the L-configuration.	1.99	1	0	dehydroascorbic acid; vitamin C	coenzyme; mouse metabolite
quinidine Quinidine: An optical isomer of quinine, extracted from the bark of the CHINCHONA tree and similar plant species. This alkaloid dampens the excitability of cardiac and skeletal muscles by blocking sodium and potassium currents across cellular membranes. It prolongs cellular ACTION POTENTIALS, and decreases automaticity. Quinidine also blocks muscarinic and alpha-adrenergic neurotransmission.. quinidine : A cinchona alkaloid consisting of cinchonine with the hydrogen at the 6-position of the quinoline ring substituted by methoxy.	5.32	50	0	cinchona alkaloid	alpha-adrenergic antagonist; anti-arrhythmia drug; antimalarial; drug allergen; EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor; EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor; muscarinic antagonist; P450 inhibitor; potassium channel blocker; sodium channel blocker
saquinavir Saquinavir: An HIV protease inhibitor which acts as an analog of an HIV protease cleavage site. It is a highly specific inhibitor of HIV-1 and HIV-2 proteases, and also inhibits CYTOCHROME P-450 CYP3A.. saquinavir : An aspartic acid derivative obtained by formal condensation of the primary amino group of (2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl]-3-hydroxy-1-phenylbutan-2-ylamine with the carboxy group of N(2)(-quinolin-2-ylcarbonyl)-L-asparagine. An inhibitor of HIV-1 protease.	3.12	1	0	L-asparagine derivative; quinolines	antiviral drug; HIV protease inhibitor
epiandrosterone epiandrosterone : A 3beta-hydroxy steroid that is (5alpha)-androstane substituted by a beta-hydroxy group at position 3 and an oxo group at position 17.	3.1	1	0	17-oxo steroid; 3beta-hydroxy steroid; androstanoid	androgen; human metabolite
linezolid [no description available]	2.61	2	0	acetamides; morpholines; organofluorine compound; oxazolidinone	antibacterial drug; protein synthesis inhibitor
indican [no description available]	2.1	1	0	beta-D-glucoside; exopolysaccharide; indolyl carbohydrate
naringin [no description available]	3.1	1	0	(2S)-flavan-4-one; 4'-hydroxyflavanones; dihydroxyflavanone; disaccharide derivative; neohesperidoside	anti-inflammatory agent; antineoplastic agent; metabolite
yatein yatein: isolated from Anthriscus sylvestris; structure in first source. dihydroanhydropodorhizol : A member of the class of butan-4-olides carrying 3,4,5-trimethoxybenzyl and (1,3-benzodioxol-5-yl)methyl substituents at positions 3 and 4 respectively.	3.12	1	0	benzodioxoles; butan-4-olide; lignan; methoxybenzenes	plant metabolite
hinokinin hinokinin: suppresses expression of both HBsAg and HBeAg. hinokinin : A lignan that is dihydrofuran-2(3H)-one (gamma-butyrolactone) substituted by a 3,4-methylenedioxybenzyl group at positions 3 and 4 (the 3R,4R-diastereoisomer).	3.12	1	0	benzodioxoles; gamma-lactone; lignan	trypanocidal drug
lignans Lignans: A class of dibenzylbutane derivatives which occurs in higher plants and in fluids (bile, serum, urine, etc.) in man and other animals. These compounds, which have a potential anti-cancer role, can be synthesized in vitro by human fecal flora. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)	2.05	1	0
1-alpha-terpineol (S)-(-)-alpha-terpineol : The (S)-enantiomer of alpha-terpineol.	3.1	1	0	alpha-terpineol	plant metabolite
diprenorphine Diprenorphine: A narcotic antagonist similar in action to NALOXONE. It is used to remobilize animals after ETORPHINE neuroleptanalgesia and is considered a specific antagonist to etorphine.	3.1	1	0	morphinane alkaloid
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
e-z cinnamic acid cinnamic acid : A monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia.. trans-cinnamic acid : The E (trans) isomer of cinnamic acid	2.02	1	0	cinnamic acid	plant metabolite
ergosterol [no description available]	3.1	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; ergostanoid; phytosterols	fungal metabolite; Saccharomyces cerevisiae metabolite
tretinoin Tretinoin: An important regulator of GENE EXPRESSION during growth and development, and in NEOPLASMS. Tretinoin, also known as retinoic acid and derived from maternal VITAMIN A, is essential for normal GROWTH; and EMBRYONIC DEVELOPMENT. An excess of tretinoin can be teratogenic. It is used in the treatment of PSORIASIS; ACNE VULGARIS; and several other SKIN DISEASES. It has also been approved for use in promyelocytic leukemia (LEUKEMIA, PROMYELOCYTIC, ACUTE).. retinoic acid : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraenoic acid substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).. all-trans-retinoic acid : A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry.	4.57	8	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.	3.49	8	0	icosa-5,8,11,14-tetraenoic acid; long-chain fatty acid; omega-6 fatty acid	Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite; mouse metabolite
resveratrol trans-resveratrol : A resveratrol in which the double bond has E configuration.	5.05	7	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).	3.76	3	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.	1.98	1	0	1,2-diacyl-sn-glycero-3-phosphocholine(1+)
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.	7.21	1	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.	3.1	1	0	ferulic acids	anti-inflammatory agent; antioxidant; apoptosis inhibitor; cardioprotective agent; MALDI matrix material; plant metabolite
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.	1.99	1	0	butyrate ester; organic heterotricyclic compound; sesquiterpene lactone	calcium channel blocker; EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor
mycophenolic acid Mycophenolic Acid: Compound derived from Penicillium stoloniferum and related species. It blocks de novo biosynthesis of purine nucleotides by inhibition of the enzyme inosine monophosphate dehydrogenase (IMP DEHYDROGENASE). Mycophenolic acid exerts selective effects on the immune system in which it prevents the proliferation of T-CELLS, LYMPHOCYTES, and the formation of antibodies from B-CELLS. It may also inhibit recruitment of LEUKOCYTES to sites of INFLAMMATION.. mycophenolate : A monocarboxylic acid anion resulting from the removal of a proton from the carboxy group of mycophenolic acid.. mycophenolic acid : A member of the class of 2-benzofurans that is 2-benzofuran-1(3H)-one which is substituted at positions 4, 5, 6, and 7 by methyl, methoxy, (2E)-5-carboxy-3-methylpent-2-en-1-yl, and hydroxy groups, respectively. It is an antibiotic produced by Penicillium brevi-compactum, P. stoloniferum, P. echinulatum and related species. An immunosuppressant, it is widely used (partiularly as its sodium salt and as the 2-(morpholin-4-yl)ethyl ester prodrug, mycophenolate mofetil) to prevent tissue rejection following organ transplants and for the treatment of certain autoimmune diseases.	3.1	1	0	2-benzofurans; gamma-lactone; monocarboxylic acid; phenols	anticoronaviral agent; antimicrobial agent; antineoplastic agent; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; environmental contaminant; immunosuppressive agent; mycotoxin; Penicillium metabolite; xenobiotic
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.	10.72	16	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
gs 4071 GS 4071: The acid form.. oseltamivir acid : A cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid which is substituted at positions 3, 4, and 5 by pentan-3-yloxy, acetamido, and amino groups, respectively (the 3R,4R,5S enantiomer). An antiviral drug, it is used as the corresponding ethyl ester prodrug, oseltamivir, to slow the spread of influenza.	2.31	1	0	acetate ester; amino acid; cyclohexenecarboxylic acid; primary amino compound	antiviral drug; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor; marine xenobiotic metabolite
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.	2.93	4	0	phenols; tertiary amino compound	antineoplastic agent; estrogen receptor antagonist; metabolite
pa 824 pretomanid: nitroimidazopyran derived from 5-nitroimidazoles; a prodrug that requires activation by a bacterial F420-depedent glucose-6-phosphate dehydrogenase (Fgd) and nitroreductase to activate components that then inhibit bacterial mycolic acid and protein synthesis; structure in first source	2.03	1	0
ketoconazole (2R,4S)-ketoconazole : A cis-1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine which dioxolane moiety has (2R,4S)-configuration.	4.81	24	0	cis-1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine
dactinomycin Dactinomycin: A compound composed of a two CYCLIC PEPTIDES attached to a phenoxazine that is derived from STREPTOMYCES parvullus. It binds to DNA and inhibits RNA synthesis (transcription), with chain elongation more sensitive than initiation, termination, or release. As a result of impaired mRNA production, protein synthesis also declines after dactinomycin therapy. (From AMA Drug Evaluations Annual, 1993, p2015)	2.01	1	0	actinomycin	mutagen
u 100480 U 100480: structure given in first source	2.25	1	0
norlevorphanol [no description available]	1.99	1	0
n-desmethylflunitrazepam N-desmethylflunitrazepam: metabolite of flunitrazepam	2	1	0
5,7,3',4'-tetramethylluteolin 5,7,3',4'-tetramethylluteolin: a flavonoid from the East Asian medicinal plant Orthosiphon spicatus; prevents oxidative inactivation of 15-lipoxygenase; structure given in first source	2.06	1	0
geraniol [no description available]	3.1	1	0	3,7-dimethylocta-2,6-dien-1-ol; monoterpenoid; primary alcohol	allergen; fragrance; plant metabolite; volatile oil component
chalcone trans-chalcone : The trans-isomer of chalcone.	2.46	2	0	chalcone	EC 3.2.1.1 (alpha-amylase) inhibitor
isosafrole isosafrole: RN given refers to cpd without isomeric designation	2.67	3	0	benzodioxoles
7-methoxyisoflavone 7-methoxyisoflavone : A methoxyisoflavone that is isoflavone substituted by a methoxy group at position 7.	2.06	1	0	7-methoxyisoflavones
citral citral: Xref geranial: geraniol is also available; Xref neral: nerol is also available; vitamin A antagonist; oxygenated monoterpene; inhibits cytosolic dehydrogenases; structure. citral : An enal that consists of octa-2,6-dienal bearing methyl substituents at positions 3 and 7. A mixture of the two geometric isomers geranial and neral, it is the major constituent (75-85%) of oil of lemon grass, the volatile oil of Cymbopogon citratus, or of C. flexuosus. It also occurs in oils of verbena, lemon, and orange.	1.99	1	0	enal; monoterpenoid; polyprenal	plant metabolite; volatile oil component
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.	2.4	2	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.	2.17	1	0	benzodioxoles; N-acylpiperidine; piperidine alkaloid; tertiary carboxamide	food component; human blood serum metabolite; NF-kappaB inhibitor; plant metabolite
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	3.28	6	0	stilbene
cannabidiol Cannabidiol: Compound isolated from Cannabis sativa extract.. cannabidiol : An cannabinoid that is cyclohexene which is substituted by a methyl group at position 1, a 2,6-dihydroxy-4-pentylphenyl group at position 3, and a prop-1-en-2-yl group at position 4.	4.32	3	0	olefinic compound; phytocannabinoid; resorcinols	antimicrobial agent; plant metabolite
arginine vasopressin Arginine Vasopressin: The predominant form of mammalian antidiuretic hormone. It is a nonapeptide containing an ARGININE at residue 8 and two disulfide-linked cysteines at residues of 1 and 6. Arg-vasopressin is used to treat DIABETES INSIPIDUS or to improve vasomotor tone and BLOOD PRESSURE.. argipressin : The predominant form of mammalian vasopressin (antidiuretic hormone). It is a nonapeptide containing an arginine at residue 8 and two disulfide-linked cysteines at residues of 1 and 6.	1.96	1	0	vasopressin	cardiovascular drug; hematologic agent; mitogen
dienestrol Dienestrol: A synthetic, non-steroidal estrogen structurally related to stilbestrol. It is used, usually as the cream, in the treatment of menopausal and postmenopausal symptoms.. dienestrol : An olefinic compound that is hexa-2,4-diene substituted by 4-hydroxyphenyl groups at positions 3 and 4 respectively.	3.1	1	0
caffeic acid trans-caffeic acid : The trans-isomer of caffeic acid.	2.02	1	0	caffeic acid	geroprotector; mouse metabolite
pongamol pongamol: from Pongamia pinnata fruits; structure in first source	2.17	1	0
captax captax: RN given refers to parent cpd. 1,3-benzothiazole-2-thiol : 1,3-Benzothiazole substituted at the 2-position with a sulfanyl group.	3.1	1	0	aryl thiol; benzothiazoles	carcinogenic agent; metabolite
2'-nitroflavone 2'-nitroflavone: has antineoplastic activity	2.02	1	0
thiothixene [no description available]	3.1	1	0	N-methylpiperazine	anticoronaviral agent
curcumin Curcumin: A yellow-orange dye obtained from tumeric, the powdered root of CURCUMA longa. It is used in the preparation of curcuma paper and the detection of boron. Curcumin appears to possess a spectrum of pharmacological properties, due primarily to its inhibitory effects on metabolic enzymes.. curcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa.	2.42	2	0	aromatic ether; beta-diketone; diarylheptanoid; enone; polyphenol	anti-inflammatory agent; antifungal agent; antineoplastic agent; biological pigment; contraceptive drug; dye; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; EC 1.8.1.9 (thioredoxin reductase) inhibitor; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; flavouring agent; food colouring; geroprotector; hepatoprotective agent; immunomodulator; iron chelator; ligand; lipoxygenase inhibitor; metabolite; neuroprotective agent; nutraceutical; radical scavenger
nootkatone nootkatone: RN given refers to cpd without isomeric designation; structure given in first source. (+)-nootkatone : A sesquiterpenoid that is 4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one which is substituted by methyl groups at positions 4 and 4a, and by an isopropenyl group at position 6 (the 4R,4aS,6R stereoisomer).	2.31	1	0	carbobicyclic compound; enone; sesquiterpenoid	fragrance; insect repellent; plant metabolite
methimazole Methimazole: A thioureylene antithyroid agent that inhibits the formation of thyroid hormones by interfering with the incorporation of iodine into tyrosyl residues of thyroglobulin. This is done by interfering with the oxidation of iodide ion and iodotyrosyl groups through inhibition of the peroxidase enzyme.. methimazole : A member of the class of imidazoles that it imidazole-2-thione in which a methyl group replaces the hydrogen which is attached to a nitrogen.	4.33	6	0	1,3-dihydroimidazole-2-thiones	antithyroid drug
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.	3.12	1	0	capsaicinoid	non-narcotic analgesic; TRPV1 agonist; voltage-gated sodium channel blocker
enclomiphene Enclomiphene: The trans or (E)-isomer of clomiphene.	2	1	0
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.	3.1	1	0	cinnamate ester; tannin	food component; plant metabolite
n-hydroxy-n'-(4-butyl-2-methylphenyl)formamidine HET0016: 20-Hydroxyeicosatetraenoic Acid synthesis inhibitor	2.03	1	0	toluenes
tamoxifen [no description available]	4.82	10	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
nadp [no description available]	4.28	19	0
6-bromoacetyl-2-dimethylaminonaphthalene 6-bromoacetyl-2-dimethylaminonaphthalene: structure in first source	2.03	1	0
valinomycin Valinomycin: A cyclododecadepsipeptide ionophore antibiotic produced by Streptomyces fulvissimus and related to the enniatins. It is composed of 3 moles each of L-valine, D-alpha-hydroxyisovaleric acid, D-valine, and L-lactic acid linked alternately to form a 36-membered ring. (From Merck Index, 11th ed) Valinomycin is a potassium selective ionophore and is commonly used as a tool in biochemical studies.. valinomycin : A twelve-membered cyclodepsipeptide composed of three repeating D-alpha-hydroxyisovaleryl-D-valyl-L-lactoyl-L-valyl units joined in sequence. An antibiotic found in several Streptomyces strains.	1.98	1	0	cyclodepsipeptide; macrocycle	antimicrobial agent; antiviral agent; bacterial metabolite; potassium ionophore
u 0126 U 0126: protein kinase kinase inhibitor; structure in first source	2.46	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
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.	2.37	2	0	cobalt salt; inorganic chloride	allergen; calcium channel blocker; sensitiser; two-colour indicator
gestodene Gestodene: synthetic steroid with progestational activity; RN given refers to (17alpha)-isomer	4.18	5	0	steroid	estrogen
quinine [no description available]	2.71	3	0	cinchona alkaloid	antimalarial; muscle relaxant; non-narcotic analgesic
1,2-bis(2-aminophenoxy)ethane n,n,n',n'-tetraacetic acid acetoxymethyl ester [no description available]	2.04	1	0
7-benzyloxyquinoline 7-benzyloxyquinoline: fluorescent substrate for cytochrome P-450 monooxygenases; structure given in first source	2.49	2	0
desdimethyltamoxifen N,N-didesmethyltamoxifen: structure in first source	3.12	1	0	stilbenoid
sch 23390 SCH 23390: a selective D1-receptor antagonist. SCH 23390 : A benzazepine that is 2,3,4,5-tetrahydro-3-benzazepine bearing a phenyl substituent at position 1, a methyl substituent at position 3, a chloro substituent at position 7 and a hydroxy substituent at position 8.	3.1	1	0	benzazepine
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.	2.01	1	0
thalifendine thalifendine: structure in first source	3.25	1	0
silybin [no description available]	3.12	1	0
uccf-029 [no description available]	2.48	2	0	organic heterotricyclic compound; organooxygen compound
ovalbumin Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.	2.1	1	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.	2.13	1	0	organic sodium salt	detergent; protein denaturant
sto 609 STO 609: structure in first source	2.04	1	0	naphthoic acid
zinc protoporphyrin ix [no description available]	2.02	1	0
digitoxigenin Digitoxigenin: 3 beta,14-Dihydroxy-5 beta-card-20(22)enolide. A cardenolide which is the aglycon of digitoxin. Synonyms: Cerberigenin; Echujetin; Evonogenin; Thevetigenin.. digitoxigenin : A 5beta-cardenolide that is 5beta-cardanolide with hydroxy substituents at the 3beta- and 14beta-positions and double bond unsaturation at C(20)-C(22).	3.1	1	0	14beta-hydroxy steroid; 3beta-hydroxy steroid
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.	2.88	4	0	ethyl ester; maleate ester	glutathione depleting agent
quercetin [no description available]	5.58	13	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]	3.51	2	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.	2.66	3	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.	2.7	3	0	monocarboxylic acid; prostaglandins Falpha	human metabolite; mouse metabolite
bergaptol 5-hydroxyfurocoumarin : A furanocoumarin which bears a hydroxy group at position 5.	3.12	1	0	5-hydroxyfurocoumarin; psoralens
biochanin a [no description available]	3.59	2	0	4'-methoxyisoflavones; 7-hydroxyisoflavones	antineoplastic agent; EC 3.5.1.99 (fatty acid amide hydrolase) inhibitor; phytoestrogen; plant metabolite; tyrosine kinase inhibitor
formononetin [no description available]	3.25	1	0	4'-methoxyisoflavones; 7-hydroxyisoflavones	phytoestrogen; plant metabolite
sterigmatocystin [no description available]	1.97	1	0	sterigmatocystins	metabolite
vitexin [no description available]	2.17	1	0	C-glycosyl compound; trihydroxyflavone	antineoplastic agent; EC 3.2.1.20 (alpha-glucosidase) inhibitor; plant metabolite; platelet aggregation inhibitor
acacetin 5,7-dihydroxy-4'-methoxyflavone : A monomethoxyflavone that is the 4'-methyl ether derivative of apigenin.	4.4	3	0	dihydroxyflavone; monomethoxyflavone	anticonvulsant; plant metabolite
apigenin Chamomile: Common name for several daisy-like plants (MATRICARIA; TRIPLEUROSPERMUM; ANTHEMIS; CHAMAEMELUM) native to Europe and Western Asia, now naturalized in the United States and Australia.	5.13	8	0	trihydroxyflavone	antineoplastic agent; metabolite
luteolin [no description available]	3.57	2	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
calcitriol dihydroxy-vitamin D3: as a major in vitro metabolite of 1alpha,25-dihydroxyvitamin D3, produced in primary cultures of neonatal human keratinocytes	2.13	1	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
scopoletin [no description available]	3.1	1	0	hydroxycoumarin	plant growth regulator; plant metabolite
vitamin k semiquinone radical vitamin K semiquinone radical: found in active preparations of vitamin K-dependent carboxylase. vitamin K : Any member of a group of fat-soluble 2-methyl-1,4-napthoquinones that exhibit biological activity against vitamin K deficiency. Vitamin K is required for the synthesis of prothrombin and certain other blood coagulation factors.	1.95	1	0
beta carotene beta Carotene: A carotenoid that is a precursor of VITAMIN A. Beta carotene is administered to reduce the severity of photosensitivity reactions in patients with erythropoietic protoporphyria (PORPHYRIA, ERYTHROPOIETIC).. provitamin A : A provitamin that can be converted into vitamin A by enzymes from animal tissues.	2	1	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.	2.37	2	0	dihydroxy monocarboxylic acid; hydroxy polyunsaturated fatty acid; leukotriene; long-chain fatty acid	human metabolite; mouse metabolite; plant metabolite; vasoconstrictor agent
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.	3.1	1	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.	1.97	1	0	fatty acid 20:3; long-chain fatty acid	fungal metabolite; human metabolite; nutraceutical
chrysoeriol chrysoeriol: isolated from leaves of Eurya japonica & E. emarginata. 4',5,7-trihydroxy-3'-methoxyflavone : The 3'-O-methyl derivative of luteolin.	3.25	1	0	monomethoxyflavone; trihydroxyflavone	antineoplastic agent; antioxidant; metabolite
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.	1.97	1	0	acrylamides; C-nitro compound; nitrofuran antibiotic; primary carboxamide
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.	3.1	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.	3.1	1	0	D3 vitamins; hydroxy seco-steroid; seco-cholestane; secondary alcohol; steroid hormone	geroprotector; human metabolite
rutin Hydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders.	1.96	1	0	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite
kaempferol [no description available]	3.13	1	0	7-hydroxyflavonol; flavonols; tetrahydroxyflavone	antibacterial agent; geroprotector; human blood serum metabolite; human urinary metabolite; human xenobiotic metabolite; plant metabolite
6-ketoprostaglandin f1 alpha 6-Ketoprostaglandin F1 alpha: The physiologically active and stable hydrolysis product of EPOPROSTENOL. Found in nearly all mammalian tissue.. 6-oxoprostaglandin F1alpha : A prostaglandin Falpha that is prostaglandin F1alpha bearing a keto substituent at the 6-position.	1.97	1	0	prostaglandins Falpha	human metabolite; mouse metabolite
harmine Harmine: Alkaloid isolated from seeds of PEGANUM HARMALA; ZYGOPHYLLACEAE. It is identical to banisterine, or telepathine, from Banisteria caapi and is one of the active ingredients of hallucinogenic drinks made in the western Amazon region from related plants. It has no therapeutic use, but (as banisterine) was hailed as a cure for postencephalitic PARKINSON DISEASE in the 1920's.. harmine : A harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7.	1.96	1	0	harmala alkaloid	anti-HIV agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; metabolite
genistein [no description available]	3.26	6	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.	2.17	1	0	antibiotic antifungal drug; macrolide antibiotic; polyene antibiotic	antiamoebic agent; antiprotozoal drug; bacterial metabolite
montelukast montelukast: a leukotriene D4 receptor antagonist	2.63	2	0	aliphatic sulfide; monocarboxylic acid; quinolines	anti-arrhythmia drug; anti-asthmatic drug; leukotriene antagonist
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.	3.1	1	0	hydroxycoumarin	antioxidant; plant metabolite; ultraviolet filter
7-hydroxycoumarin 7-oxycoumarin: derivatives have anti-oxidant properties. umbelliferone : A hydroxycoumarin that is coumarin substituted by a hydroxy group ay position 7.	3.48	2	0	hydroxycoumarin	fluorescent probe; food component; plant metabolite
apigenin dimethylether apigenin dimethylether: a dimethoxy analog of apigenin from roots of Rhus undulata and possibly other plants. apigenin 7,4'-dimethyl ether : A dimethoxyflavone that is the 7,4'-dimethyl ether derivative of apigenin.	1.99	1	0	dimethoxyflavone; monohydroxyflavone	plant metabolite
baicalein [no description available]	3.1	1	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.	5.04	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]	3.25	1	0	3'-hydroxyflavonoid; monomethoxyflavone; trihydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; antioxidant; apoptosis inducer; bone density conservation agent; cardioprotective agent; plant metabolite; tropomyosin-related kinase B receptor agonist; vasodilator agent
fisetin [no description available]	3.1	1	0	3'-hydroxyflavonoid; 7-hydroxyflavonol; tetrahydroxyflavone	anti-inflammatory agent; antioxidant; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; geroprotector; metabolite; plant metabolite
galangin 5,7-dihydroxyflavonol: antimicrobial from the twigs of Populus nigra x Populus deltoides; structure in first source. galangin : A 7-hydroxyflavonol with additional hydroxy groups at positions 3 and 5 respectively; a growth inhibitor of breast tumor cells.	4.54	4	0	7-hydroxyflavonol; trihydroxyflavone	antimicrobial agent; EC 3.1.1.3 (triacylglycerol lipase) inhibitor; plant metabolite
gossypin gossypin: do not confuse with gossypin(e) which is synonym for choline. gossypin : A glycosyloxyflavone that is gossypetin attached to a beta-D-glucopyranosyl residue at position 8 via a glycosidic linkage.	2.06	1	0	7-hydroxyflavonol; glycosyloxyflavone; monosaccharide derivative; pentahydroxyflavone	neuroprotective agent; plant metabolite
hispidulin hispidulin : A monomethoxyflavone that is scutellarein methylated at position 6.	2.71	3	0	monomethoxyflavone; trihydroxyflavone	anti-inflammatory agent; anticonvulsant; antineoplastic agent; antioxidant; apoptosis inducer; plant metabolite
3-methylquercetin isorhamnetin : A monomethoxyflavone that is quercetin in which the hydroxy group at position 3' is replaced by a methoxy group.	3.25	1	0	7-hydroxyflavonol; monomethoxyflavone; tetrahydroxyflavone	anticoagulant; EC 1.14.18.1 (tyrosinase) inhibitor; metabolite
kaempferide kaempferide: structure in first source. kaempferide : A monomethoxyflavone that is the 4'-O-methyl derivative of kaempferol.	3.13	1	0	7-hydroxyflavonol; monomethoxyflavone; trihydroxyflavone	antihypertensive agent; metabolite
morin morin: a light yellowish pigment found in the wood of old fustic (Chlorophora tinctoria). morin : A pentahydroxyflavone that is 7-hydroxyflavonol bearing three additional hydroxy substituents at positions 2' 4' and 5.	2.01	1	0	7-hydroxyflavonol; pentahydroxyflavone	angiogenesis modulating agent; anti-inflammatory agent; antibacterial agent; antihypertensive agent; antineoplastic agent; antioxidant; EC 5.99.1.2 (DNA topoisomerase) inhibitor; hepatoprotective agent; metabolite; neuroprotective agent
myricetin [no description available]	3.25	1	0	7-hydroxyflavonol; hexahydroxyflavone	antineoplastic agent; antioxidant; cyclooxygenase 1 inhibitor; food component; geroprotector; hypoglycemic agent; plant 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.	2.07	1	0	dihydroxyflavone; monomethoxyflavone	angiogenesis inhibitor; antineoplastic agent; cyclooxygenase 2 inhibitor; plant metabolite
coumestrol Coumestrol: A daidzein derivative occurring naturally in forage crops which has some estrogenic activity.. coumestrol : A member of the class of coumestans that is coumestan with hydroxy substituents at positions 3 and 9.	2.05	1	0	coumestans; delta-lactone; polyphenol	anti-inflammatory agent; antioxidant; plant metabolite
pterostilbene [no description available]	3.25	1	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.	2.07	1	0	alkyl caffeate ester	anti-inflammatory agent; antibacterial agent; antineoplastic agent; antioxidant; antiviral agent; immunomodulator; metabolite; neuroprotective agent
prunetin prunetin: reduces herpes virus-1 plaque formation. prunetin : A hydroxyisoflavone that is genistein in which the hydroxy group at position 7 is replaced by a methoxy group.	2.06	1	0	7-methoxyisoflavones; hydroxyisoflavone	anti-inflammatory agent; EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor; EC 1.3.1.22 [3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+))] inhibitor; metabolite
arborinine arborinine: structure	1.99	1	0	acridines
ginkgolic acid [no description available]	2.05	1	0	hydroxybenzoic acid
7-hydroxyflavone 7-hydroxyflavone : A hydroxyflavonoid in which the flavone nucleus is substituted at position 7 by a hydroxy group.	4.23	5	0	hydroxyflavonoid
4',7-dihydroxyflavone 4',7-dihydroxyflavone: inducer of nod gene. 4',7-dihydroxyflavone : A dihydroxyflavone in which the two hydroxy substituents are located at positions 4' and 7.	2.05	1	0	dihydroxyflavone	metabolite
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.	2.05	1	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.	3.8	3	0	4-hydroxy steroid	metabolite
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.	3.48	2	0	retinoic acid	antineoplastic agent; keratolytic drug; teratogenic 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.	2.02	1	0	thromboxanes B	human metabolite; mouse metabolite
20-hydroxy-5,8,11,14-eicosatetraenoic acid 20-hydroxy-5,8,11,14-eicosatetraenoic acid: stimulator of renal sodium, potassium atpase; RN given is for the (all-Z) isomer. 20-HETE : A HETE that consists of arachidonic acid bearing a hydroxy substituent at position 20.	2.03	1	0	HETE; hydroxy monocarboxylic acid	human metabolite; mouse metabolite
hyodeoxycholic acid hyodeoxycholic acid: differs from deoxycholic acid in that the 6 alpha-OH is in the 12 position in the former; RN given refers to (3alpha,5beta,6alpha)-isomer. hyodeoxycholic acid : A member of the class of 5beta-cholanic acids that is (5beta)-cholan-24-oic acid substituted by alpha-hydroxy groups at positions 3 and 6.	3.1	1	0	5beta-cholanic acids; 6alpha,20xi-murideoxycholic acid; bile acid; C24-steroid	human metabolite; mouse metabolite
codeine [no description available]	3.1	1	0	morphinane alkaloid; organic heteropentacyclic compound	antitussive; drug allergen; environmental contaminant; opioid analgesic; opioid receptor agonist; prodrug; xenobiotic
cyclosporine ramihyphin A: one of the metabolites produced by Fusarium sp. S-435; RN given refers to cpd with unknown MF	2.81	3	0	homodetic cyclic peptide	anti-asthmatic drug; anticoronaviral agent; antifungal agent; antirheumatic drug; carcinogenic agent; dermatologic drug; EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; geroprotector; immunosuppressive agent; metabolite
3-amino-1,4-dimethyl-5h-pyrido(4,3-b)indole 3-amino-1,4-dimethyl-5H-pyrido(4,3-b)indole: structure	2	1	0	pyridoindole
3-amino-1-methyl-5h-pyrido(4,3-b)indole 3-amino-1-methyl-5H-pyrido(4,3-b)indole: structure	1.96	1	0	pyridoindole
hydromorphone Hydromorphone: An opioid analgesic made from MORPHINE and used mainly as an analgesic. It has a shorter duration of action than morphine.. hydromorphone : A morphinane alkaloid that is a hydrogenated ketone derivative of morphine. A semi-synthetic drug, it is a centrally acting pain medication of the opioid class.	3.1	1	0	morphinane alkaloid; organic heteropentacyclic compound	mu-opioid receptor agonist; opioid analgesic
nalmefene nalmefene: RN given refers to 5-alpha isomer	3.1	1	0	morphinane alkaloid
nalorphine Nalorphine: A narcotic antagonist with some agonist properties. It is an antagonist at mu opioid receptors and an agonist at kappa opioid receptors. Given alone it produces a broad spectrum of unpleasant effects and it is considered to be clinically obsolete.	3.1	1	0	morphinane alkaloid
naloxone Naloxone: A specific opiate antagonist that has no agonist activity. It is a competitive antagonist at mu, delta, and kappa opioid receptors.. naloxone : A synthetic morphinane alkaloid that is morphinone in which the enone double bond has been reduced to a single bond, the hydrogen at position 14 has been replaced by a hydroxy group, and the methyl group attached to the nitrogen has been replaced by an allyl group. A specific opioid antagonist, it is used (commonly as its hydrochloride salt) to reverse the effects of opioids, both following their use of opioids during surgery and in cases of known or suspected opioid overdose.	3.1	1	0	morphinane alkaloid; organic heteropentacyclic compound; tertiary alcohol	antidote to opioid poisoning; central nervous system depressant; mu-opioid receptor antagonist
oxycodone Oxycodone: A semisynthetic derivative of CODEINE.. oxycodone : A semisynthetic opioid of formula C18H21NO4 that is derived from thebaine. It is a moderately potent opioid analgesic, generally used for relief of moderate to severe pain.	3.1	1	0	organic heteropentacyclic compound; semisynthetic derivative	antitussive; mu-opioid receptor agonist; opioid analgesic
oxymorphone Oxymorphone: An opioid analgesic with actions and uses similar to those of MORPHINE, apart from an absence of cough suppressant activity. It is used in the treatment of moderate to severe pain, including pain in obstetrics. It may also be used as an adjunct to anesthesia. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1092)	3.1	1	0	morphinane alkaloid
6alpha-hydroxy-17beta-estradiol 6alpha-hydroxy-17beta-estradiol : A 4-hydroxy steroid that consists of 17beta-estradiol bearing an additional 6alpha-hydroxy substituent.	3.1	1	0	6alpha-hydroxy steroid
alvocidib alvocidib: structure given in first source. alvocidib : A synthetic dihydroxyflavone that is 5,7-dihydroxyflavone which is substituted by a 3-hydroxy-1-methylpiperidin-4-yl group at position 8 and by a chlorine at the 2' position (the (-)-3S,4R stereoisomer). A cyclin-dependent kinase 9 (CDK9) inhibitor, it has been studied for the treatment of acute myeloid leukaemia, arthritis and atherosclerotic plaque formation.	2.31	1	0	dihydroxyflavone; hydroxypiperidine; monochlorobenzenes; tertiary amino compound	antineoplastic agent; antirheumatic drug; apoptosis inducer; EC 2.7.11.22 (cyclin-dependent kinase) inhibitor
morphine Meconium: The thick green-to-black mucilaginous material found in the intestines of a full-term fetus. It consists of secretions of the INTESTINAL GLANDS; BILE PIGMENTS; FATTY ACIDS; AMNIOTIC FLUID; and intrauterine debris. It constitutes the first stools passed by a newborn.	3.1	1	0	morphinane alkaloid; organic heteropentacyclic compound; tertiary amino compound	anaesthetic; drug allergen; environmental contaminant; geroprotector; mu-opioid receptor agonist; opioid analgesic; plant metabolite; vasodilator agent; xenobiotic
4-amino-5-chloro-N-[(3R,4S)-1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl]-2-methoxybenzamide [no description available]	2.41	1	0	benzamides
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.	2.69	3	0	1,4-benzoquinones; lactam; macrocycle	antimicrobial agent; apoptosis inducer; herbicide; Hsp90 inhibitor; tyrosine kinase inhibitor
nalbuphine Nalbuphine: A narcotic used as a pain medication. It appears to be an agonist at KAPPA RECEPTORS and an antagonist or partial agonist at MU RECEPTORS.	3.1	1	0	organic heteropentacyclic compound	mu-opioid receptor antagonist; opioid analgesic
cgp 77675 CGP 77675: belongs to class of substituted 5,7-diphenyl-pyrrolo(2,3-d)pyrimidines; structure in first source	2.03	1	0
onapristone onapristone: induces vaginal bleeding and luteal regression in monkeys; structure given in first source; progesterone antagonist	3.12	1	0
kn 93 KN 93: reduces dopamine content in PC12h cells. KN-93 : A sulfonamide resulting from the formal condensation of p-methoxybenzenesulfonic acid with the anilino nitrogen of 2-(aminomethyl)-N-(2-hydroxyethyl)aniline in which the hydrogens of the primary amino group have been replaced by methyl and p-chlorocinnamyl groups. KN-93 is a selective inhibitor of Ca(2+)/calmodulin-dependent protein kinase II.	2.04	1	0	monochlorobenzenes; monomethoxybenzene; primary alcohol; sulfonamide; tertiary amino compound	EC 2.7.11.17 (Ca(2+)/calmodulin-dependent protein kinase) inhibitor; geroprotector
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.	1.98	1	0	phosphatidylcholine(1+)
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).	3.1	1	0	cinnamyl alcohol	plant metabolite
ethyl caffeate (E)-ethyl 3-(3,4-dihydroxyphenyl)prop-2-enoate: structure in first source. ethyl trans-caffeate : An ethyl ester resulting from the formal condensation of the carboxy group of trans-caffeic acid with ethanol.	2.02	1	0	alkyl caffeate ester; ethyl ester; hydroxycinnamic acid	anti-inflammatory agent; antineoplastic agent; metabolite
isorhamnetin 3-o-glucoside isorhamnetin 3-O-glucoside: from the flowers of Persea gratissima; structure in first source. isorhamnetin 3-O-beta-D-glucopyranoside : A glycosyloxyflavone that is isorhamnetin substituted at position 3 by a beta-D-glucosyl residue.	2.06	1	0	beta-D-glucoside; glycosyloxyflavone; monomethoxyflavone; monosaccharide derivative; trihydroxyflavone	metabolite
ligustilide ligustilide: found in Umbelliferae plants; RN given refers to cpd without isomeric designation; structure in first source	2.05	1	0	butenolide	metabolite
fluvoxamine Fluvoxamine: A selective serotonin reuptake inhibitor that is used in the treatment of DEPRESSION and a variety of ANXIETY DISORDERS.. fluvoxamine : An oxime O-ether that is benzene substituted by a (1E)-N-(2-aminoethoxy)-5-methoxypentanimidoyl group at position 1 and a trifluoromethyl group at position 4. It is a selective serotonin reuptake inhibitor that is used for the treatment of obsessive-compulsive disorder.	3.8	3	0	(trifluoromethyl)benzenes; 5-methoxyvalerophenone O-(2-aminoethyl)oxime	antidepressant; anxiolytic drug; serotonin uptake inhibitor
5-hydroxy-3,3',4',7-tetramethoxyflavone 5-hydroxy-3,7,3',4'-tetramethoxyflavone: from the rhizome of Kaempferia parviflora; inhibits monocyte adhesion and cellular reactive oxygen species production in human umbilical vein endothelial cells. 5-hydroxy-3,3',4',7-tetramethoxyflavone : A monohydroxyflavone that is 5-hydroxyflavone which is substituted by methoxy groups at positions 3,3',4' and 7.	2.08	1	0	3'-methoxyflavones; monohydroxyflavone; tetramethoxyflavone	plant metabolite
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)	1.97	1	0
6,7-dihydroxyflavone 6,7-dihydroxyflavone: intensifies effect of antibiotics on Staphylococcus aureus; structure in first source	2.05	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	3.66	2	0
Isoliquiritigenin 4,4'-dimethyl ether [no description available]	2.06	1	0	chalcones
ethylmorphine Ethylmorphine: A narcotic analgesic and antitussive. It is metabolized in the liver by ETHYLMORPHINE-N-DEMETHYLASE and used as an indicator of liver function.	1.96	1	0	morphinane alkaloid
levorphanol Levorphanol: A narcotic analgesic that may be habit-forming. It is nearly as effective orally as by injection.	3.1	1	0	morphinane alkaloid
naltrexone Naltrexone: Derivative of noroxymorphone that is the N-cyclopropylmethyl congener of NALOXONE. It is a narcotic antagonist that is effective orally, longer lasting and more potent than naloxone, and has been proposed for the treatment of heroin addiction. The FDA has approved naltrexone for the treatment of alcohol dependence.. naltrexone : An organic heteropentacyclic compound that is naloxone substituted in which the allyl group attached to the nitrogen is replaced by a cyclopropylmethyl group. A mu-opioid receptor antagonist, it is used to treat alcohol dependence.	3.1	1	0	cyclopropanes; morphinane-like compound; organic heteropentacyclic compound	antidote to opioid poisoning; central nervous system depressant; environmental contaminant; mu-opioid receptor antagonist; xenobiotic
dextromethorphan Dextromethorphan: Methyl analog of DEXTRORPHAN that shows high affinity binding to several regions of the brain, including the medullary cough center. This compound is an NMDA receptor antagonist (RECEPTORS, N-METHYL-D-ASPARTATE) and acts as a non-competitive channel blocker. It is one of the widely used ANTITUSSIVES, and is also used to study the involvement of glutamate receptors in neurotoxicity.. dextromethorphan : A 6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene in which the sterocenters at positions 4a, 10 and 10a have S-configuration. It is a prodrug of dextrorphan and used as an antitussive drug for suppressing cough.	2.7	3	0	6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene	antitussive; environmental contaminant; neurotoxin; NMDA receptor antagonist; oneirogen; prodrug; xenobiotic
indinavir sulfate Indinavir: A potent and specific HIV protease inhibitor that appears to have good oral bioavailability.	3.12	1	0	dicarboxylic acid diamide; N-(2-hydroxyethyl)piperazine; piperazinecarboxamide	HIV protease inhibitor
7-hydroxy-4-trifluoromethylcoumarin 7-hydroxy-4-trifluoromethylcoumarin: structure given in first source	1.99	1	0
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	2.67	3	0	cysteinium	fundamental metabolite
normorphine normorphine: RN given refers to (5 alpha,6 alpha)-isomer	3.1	1	0	morphinane alkaloid
bergamottin bergamottin: constituent of bergamot oil; structure given in first source	4.08	2	0	furanocoumarin	metabolite
pinostilbene pinostilbene: structure in first source. 3-methoxy-4',5-dihydroxy-trans-stilbene : A stilbenoid that is trans-resveratrol in which one of the meta-hydroxy groups is converted to the corresponding methyl ether.	3.25	1	0	stilbenol
pafuramidine pafuramidine: a prodrug of furamidine	2.03	1	0
l 754394 L 754394: a potent and specific inhibitor of the HIV-1 protease; structure given in first source	3.12	1	0
naltrindole benzofuran naltrindole benzofuran: structure given in first source	3.1	1	0	morphinane alkaloid
vx680 [no description available]	2.41	1	0	N-arylpiperazine
naltrindole naltrindole: delta opioid receptor antagonist	3.1	1	0	isoquinolines
3,5-dihydroxy-4'-methoxystilbene 4'-methoxyresveratrol: has anti-inflammatory effects in cell culture model	3.25	1	0
9-cis-retinal 9-cis-retinal : A retinal in which the double bond at position 9 has cis configuration, whilst the remaining acyclic double bonds have trans configuration.	2	1	0	retinal
6',7'-dihydroxybergamottin 6',7'-dihydroxybergamottin: structure given in first source	3.12	1	0	psoralens
rilpivirine [no description available]	3.25	4	0	aminopyrimidine; nitrile	EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor; HIV-1 reverse transcriptase inhibitor
19-hydroxycholesterol 19-hydroxycholesterol: structure given in first source	3.1	1	0	cholestanoid
opc-67683 OPC-67683: an antitubercular agent	2.03	1	0	piperidines
verlukast verlukast: LTD4 receptor antagonist	2.01	1	0
borneol [no description available]	3.1	1	0	borneol
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.	2	1	0	imidazolidine-2,4-dione; nitrofuran antibiotic; organonitrogen heterocyclic antibiotic; organooxygen heterocyclic antibiotic	antibacterial drug; antiinfective agent; hepatotoxic agent
tubacin tubacin: inhibits histone deacetylase 6; structure in first source	2.21	1	0	1,3-oxazoles
sq-23377 Ionomycin: A divalent calcium ionophore that is widely used as a tool to investigate the role of intracellular calcium in cellular processes.. ionomycin : A very long-chain fatty acid that is docosa-10,16-dienoic acid which is substituted by methyl groups at positions 4, 6, 8, 12, 14, 18 and 20, by hydroxy groups at positions 11, 19 and 21, and by a (2',5-dimethyloctahydro-2,2'-bifuran-5-yl)ethanol group at position 21. An ionophore produced by Streptomyces conglobatus, it is used in research to raise the intracellular level of Ca(2+) and as a research tool to understand Ca(2+) transport across biological membranes.	2.42	2	0	cyclic ether; enol; polyunsaturated fatty acid; very long-chain fatty acid	calcium ionophore; metabolite
vorozole vorozole: structure given in first source; vorozole/R 83842 is ((+)/dextro-isomer), RN 129731-10-8; R 83839 ((-)/levo-isomer)	2.05	1	0	benzotriazoles
panobinostat Panobinostat: An indole and hydroxamic acid derivative that acts as a HISTONE DEACETYLASE inhibitor. It is used as an antineoplastic agent in combination with BORTEZOMIB and DEXAMETHASONE for the treatment of MULTIPLE MYELOMA.. panobinostat : A hydroxamic acid obtained by formal condensation of the carboxy group of (2E)-3-[4-({[2-(2-methylindol-3-yl)ethyl]amino}methyl)phenyl]prop-2-enoic acid with the amino group of hydroxylamine. A histone deacetylase inhibitor used (as its lactate salt) in combination with bortezomib and dexamethasone for the treatment of multiple myeloma.	2.31	1	0	cinnamamides; hydroxamic acid; methylindole; secondary amino compound	angiogenesis modulating agent; antineoplastic agent; EC 3.5.1.98 (histone deacetylase) inhibitor
staurosporine staurosporinium : Conjugate acid of staurosporine.	1.98	1	0	ammonium ion derivative
6-(4-chlorophenyl)imidazo(2,1-b)(1,3)thiazole-5-carbaldehyde o-(3,4-dichlorobenzyl)oxime 6-(4-chlorophenyl)imidazo(2,1-b)(1,3)thiazole-5-carbaldehyde O-(3,4-dichlorobenzyl)oxime: a constitutive androstane receptor agonist; structure in first source	2.13	1	0
dov 216303 [no description available]	2.1	1	0
gambogic acid gambogic acid: RN given refers to (1R-(1alpha,1(Z),3abeta,5alpha,11beta,14aS*))-isomer	2.03	1	0	pyranoxanthones	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	2.02	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).	2.41	2	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
norcodeine norcodeine: RN given refers to (5 alpha,6 alpha)-isomer. norcodeine : A morphinane-like compound that is the N-demethylated derivative of codeine.	3.1	1	0	morphinane alkaloid
pifithrin-alpha [no description available]	3.25	1	0
4-hydroxyestrone 4-hydroxyestrone : A 4-hydroxy steroid that is estrone substituted by a hydroxy group at position 4.	3.1	1	0	17-oxo steroid; 3-hydroxy steroid; 4-hydroxy steroid; catechols; phenolic steroid	carcinogenic agent; estrogen; human urinary metabolite
3'-methoxy-4'-nitroflavone 3'-methoxy-4'-nitroflavone: structure given in first source	2.72	3	0
4-fluoroestradiol 4-fluoroestradiol: RN given refers to unlabeled (17 beta)-isomer	2.13	1	0
11 beta-hydroxyandrosterone 11 beta-hydroxyandrosterone: RN given refers to (3alpha,5alpha,11beta)-isomer; structure	3.1	1	0	3-hydroxy steroid	androgen
ko 143 [no description available]	2.08	1	0	beta-carbolines; tert-butyl ester
2-hydroxyestriol 2-hydroxyestriol: structure	3.1	1	0
jwh 018 1-pentyl-3-(1-naphthoyl)indole: structure in first source	2.08	1	0	indolecarboxamide
demethylmirtazapine demethylmirtazapine: structure in first source. N-demethylmirtazapine : A benzazepine metabolite resulting from demethylation of the antidpressant, mirtazapine.	2	1	0	benzazepine; tetracyclic antidepressant	alpha-adrenergic antagonist; anxiolytic drug; H1-receptor antagonist; histamine antagonist; human xenobiotic metabolite; serotonergic antagonist
vinflunine vinflunine: inhibits tubulin assembly; structure in first source. vinflunine : An organic heteropentacyclic compound and an organic heterotetracyclic compound that is vinorelbine in which the tetrahydropyridine moiety of the heterotetracyclic part of the molecule has been redced to the corresponding piperidine, and in which the ethyl group attached to this ring has been replaced by a 1,1-difluoroethyl group.	2.03	1	0	acetate ester; methyl ester; organic heteropentacyclic compound; organic heterotetracyclic compound; semisynthetic derivative; vinca alkaloid	antineoplastic agent
4-(2-phenyl-5,7-bis(trifluoromethyl)pyrazolo(1,5-a)pyrimidin-3-yl)phenol 4-(2-phenyl-5,7-bis(trifluoromethyl)pyrazolo(1,5-a)pyrimidin-3-yl)phenol: a selective estrogen receptor modulator	2.1	1	0	pyrazoles; ring assembly
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	1.96	1	0
monomethyl auristatin e [no description available]	2.31	1	0
at 13387 (2,4-dihydroxy-5-isopropylphenyl)-(5-(4-methylpiperazin-1-ylmethyl)-1,3-dihydroisoindol-2-yl)methanone: structure in first source. onalespib : A member of the class of isoindoles that is isoindole in which the amino group has been acylated by a 2,4-dihydroxy-5-isopropylbenzoyl group and in which position 5 of the isoidole moiety has been substituted by a (4-methylpiperazin-1-yl)methyl group. A second-generation Hsp90 inhibitor.	2.13	1	0	benzamides; isoindoles; N-alkylpiperazine; resorcinols; tertiary carboxamide	antineoplastic agent; Hsp90 inhibitor
dextrothyroxine [no description available]	2.31	1	0
chamaechromone chamaechromone: an anti-hepatitis B virus agent isolated from Stellera chamaejasme; structure in first source	2.1	1	0
2-(4-(3-methyl-2-thienyl)phenyl)propionic acid 2-(4-(3-methyl-2-thienyl)phenyl)propionic acid: structure given in first source	2	1	0
lilopristone lilopristone: structure given in first source; progesterone antagonist	3.12	1	0
aflatoxin g1 aflatoxin G1: RN given refers to (7aR-cis)-isomer & is from 9th CI Form Index	1.97	1	0
ludartin ludartin: a TRPA1 channel activator; structure in first source	2.05	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.	2.68	3	0	aflatoxin; aromatic ether; aromatic ketone; tertiary alcohol	Aspergillus metabolite; human xenobiotic metabolite; mammalian metabolite
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	2.69	3	0	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.	2.05	1	0
azamulin azamulin: a Cyp3A inhibitor; structure in first source	3.12	1	0
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.	1.97	1	0	peptide hormone
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	2.38	2	0	1,2-diacyl-sn-glycero-3-phosphocholine
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	1	0	3',5'-cyclic purine nucleotide
chiniofon Hydroxyquinolines: The 8-hydroxy derivatives inhibit various enzymes and their halogenated derivatives, though neurotoxic, are used as topical anti-infective agents, among other uses.	1.95	1	0
gdc 0449 HhAntag691: inhibits the hedgehog pathway and ABC transporters; has antineoplastic activity	2.17	1	0	benzamides; monochlorobenzenes; pyridines; sulfone	antineoplastic agent; Hedgehog signaling pathway inhibitor; SMO receptor antagonist; teratogenic agent
pci 32765 ibrutinib: a Btk protein inhibitor. ibrutinib : A member of the class of acrylamides that is (3R)-3-[4-amino-3-(4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine in which the piperidine nitrogen is replaced by an acryloyl group. A selective and covalent inhibitor of the enzyme Bruton's tyrosine kinase, it is used for treatment of B-cell malignancies.	2.31	1	0	acrylamides; aromatic amine; aromatic ether; N-acylpiperidine; pyrazolopyrimidine; tertiary carboxamide	antineoplastic agent; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor
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.	2.48	2	0	biphenyls; carbamate ester; carboxamide; imidazoles; valine derivative	antiviral drug; nonstructural protein 5A inhibitor
piperidines Piperidines: A family of hexahydropyridines.	2.03	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.	2.75	3	0
dinaciclib [no description available]	2.31	1	0	pyrazolopyrimidine
tubastatin a [no description available]	2.21	1	0	hydroxamic acid; pyridoindole; tertiary amino compound	EC 3.5.1.98 (histone deacetylase) inhibitor
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.	3.29	6	0
AM2201 1-(5-fluoropentyl)-3-(1-naphthoyl)indole: a cannabimimetic; structure in first source	2.08	1	0	indolecarboxamide
lesinurad lesinurad: a uric acid reabsorption inhibitor. lesinurad : A member of the class of triazoles that is [(3-bromo-1,2,4-triazol-5-yl)sulfanyl]acetic acid substituted at position 1 of the triazole ring by a 4-cyclopropylnaphthalen-1-yl group. Used for treatment of gout.	2.72	2	0	aryl sulfide; cyclopropanes; monocarboxylic acid; naphthalenes; organobromine compound; triazoles	uricosuric drug
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	3.08	5	0	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
novobiocin Novobiocin: An antibiotic compound derived from Streptomyces niveus. It has a chemical structure similar to coumarin. Novobiocin binds to DNA gyrase, and blocks adenosine triphosphatase (ATPase) activity. (From Reynolds, Martindale The Extra Pharmacopoeia, 30th ed, p189). novobiocin : A coumarin-derived antibiotic obtained from Streptomyces niveus.	3.1	1	0	carbamate ester; ether; hexoside; hydroxycoumarin; monocarboxylic acid amide; monosaccharide derivative; phenols	antibacterial agent; antimicrobial agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; Escherichia coli metabolite; hepatoprotective agent
tetracycline Tetracycline: A naphthacene antibiotic that inhibits AMINO ACYL TRNA binding during protein synthesis.. tetracycline : A broad-spectrum polyketide antibiotic produced by the Streptomyces genus of actinobacteria.	3.1	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.	2.05	1	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.	1.97	1	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.	4.13	16	0	benzenes; hydroxycoumarin; methyl ketone
4-hydroxycoumarin 2-hydroxychromone: structure	3.1	1	0	hydroxycoumarin
teriflunomide [no description available]	2.06	1	0	(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.	2.03	1	0
transforming growth factor beta Transforming Growth Factor beta: A factor synthesized in a wide variety of tissues. It acts synergistically with TGF-alpha in inducing phenotypic transformation and can also act as a negative autocrine growth factor. TGF-beta has a potential role in embryonal development, cellular differentiation, hormone secretion, and immune function. TGF-beta is found mostly as homodimer forms of separate gene products TGF-beta1, TGF-beta2 or TGF-beta3. Heterodimers composed of TGF-beta1 and 2 (TGF-beta1.2) or of TGF-beta2 and 3 (TGF-beta2.3) have been isolated. The TGF-beta proteins are synthesized as precursor proteins.	2.74	3	0
phytoestrogens Phytoestrogens: Compounds derived from plants, primarily ISOFLAVONES that mimic or modulate endogenous estrogens, usually by binding to ESTROGEN RECEPTORS.	2.05	1	0
cfi-400945 [no description available]	2.41	1	0
acp-196 acalabrutinib: inhibits Bruton’s tyrosine kinase; has antineoplastic activity. acalabrutinib : A member of the class of imidazopyrazines that is imidazo[1,5-a]pyrazine substituted by 4-(pyridin-2-ylcarbamoyl)phenyl, (2S)-1-(but-2-ynoyl)pyrrolidin-2-yl, and amino groups at positions 1, 3 and 8, respectively. It is an irreversible second-generation Bruton's tyrosine kinase (BTK) inhibitor that is approved by the FDA for the treatment of adult patients with mantle cell lymphoma (MCL) who have received at least one prior therapy.	2.31	1	0	aromatic amine; benzamides; imidazopyrazine; pyridines; pyrrolidinecarboxamide; secondary carboxamide; tertiary carboxamide; ynone	antineoplastic agent; apoptosis inducer; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor
s-nitroglutathione S-nitroglutathione: structure in first source	2.03	1	0
nitrophenols Nitrophenols: PHENOLS carrying nitro group substituents.	2.44	2	0
centrinone centrinone: a polo-like kinase 4 inhibitor; structure in first source	2.41	1	0
lipofectamine Lipofectamine: mediates gene transfer; a polycationic lipid reagent	1.99	1	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.	2.1	1	0
ferric ammonium citrate ferric ammonium citrate: RN given refers to unspecified NH4-Fe(+3) salt. ferric ammonium citrate : A mixture of indefinite composition that contains ferric and ammonium cations and citrate(3-) anions, ferric ammonium citrate may be obtained as red crystals or a brownish yellow powder or as green crystals or powder. It is added to foods as an acidity regulator and anticaking agent. It is also used as a positive oral contrast agent in magnetic resonance imaging, and was formerly administered orally as a source of iron for the treatment of iron-deficiency anaemia.	2.03	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.	2.03	1	0
moxidectin moxidectin: family of macrolide antibiotics with insecticidal & acaricidal activity	2	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).	2.72	3	0
clivorine clivorine: isolated from Ligularia dentata; structure in first source	2.03	1	0
r 1530 [no description available]	2.41	1	0
cyclic gmp Cyclic GMP: Guanosine cyclic 3',5'-(hydrogen phosphate). A guanine nucleotide containing one phosphate group which is esterified to the sugar moiety in both the 3'- and 5'-positions. It is a cellular regulatory agent and has been described as a second messenger. Its levels increase in response to a variety of hormones, including acetylcholine, insulin, and oxytocin and it has been found to activate specific protein kinases. (From Merck Index, 11th ed). 3',5'-cyclic GMP : A 3',5'-cyclic purine nucleotide in which the purine nucleobase is specified as guanidine.	7.02	1	0	3',5'-cyclic purine nucleotide; guanyl ribonucleotide	Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
guanine [no description available]	2.4	2	0	2-aminopurines; oxopurine; purine nucleobase	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
folic acid folcysteine: used to promote fertility in chickens. vitamin B9 : Any B-vitamin that exhibits biological activity against vitamin B9 deficiency. Vitamin B9 refers to the many forms of folic acid and its derivatives, including tetrahydrofolic acid (the active form), methyltetrahydrofolate (the primary form found in blood), methenyltetrahydrofolate, folinic acid amongst others. They are present in abundance in green leafy vegetables, citrus fruits, and animal products. Lack of vitamin B9 leads to anemia, a condition in which the body cannot produce sufficient number of red blood cells. Symptoms of vitamin B9 deficiency include fatigue, muscle weakness, and pale skin.	2.15	1	0	folic acids; N-acyl-amino acid	human metabolite; mouse metabolite; nutrient
rifampin Rifampin: A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)	4.6	8	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
clozapine Clozapine: A tricylic dibenzodiazepine, classified as an atypical antipsychotic agent. It binds several types of central nervous system receptors, and displays a unique pharmacological profile. Clozapine is a serotonin antagonist, with strong binding to 5-HT 2A/2C receptor subtype. It also displays strong affinity to several dopaminergic receptors, but shows only weak antagonism at the dopamine D2 receptor, a receptor commonly thought to modulate neuroleptic activity. Agranulocytosis is a major adverse effect associated with administration of this agent.. clozapine : A benzodiazepine that is 5H-dibenzo[b,e][1,4]diazepine substituted by a chloro group at position 8 and a 4-methylpiperazin-1-yl group at position 11. It is a second generation antipsychotic used in the treatment of psychiatric disorders like schizophrenia.	3.1	1	0	benzodiazepine; N-arylpiperazine; N-methylpiperazine; organochlorine compound	adrenergic antagonist; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; environmental contaminant; GABA antagonist; histamine antagonist; muscarinic antagonist; second generation antipsychotic; serotonergic antagonist; xenobiotic
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.	2.21	1	0	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger
norclozapine norclozapine: structure given in first source. N-desmethylclozapine : A dibenzodoazepine substituted with chloro and piperazino groups which is a major metabolite of clozapine; a potent and selective 5-HT2C serotonin receptor antagonist.	3.1	1	0	dibenzodiazepine; organochlorine compound; piperazines	delta-opioid receptor agonist; metabolite; serotonergic antagonist
tirapazamine Tirapazamine: A triazine derivative that introduces breaks into DNA strands in hypoxic cells, sensitizing tumor cells to the cytotoxic activity of other drugs and radiation.. tirapazamine : A member of the class of benzotriazines that is 1,2,4-benzotriazine carrying an amino substituent at position 3 and two oxido substituents at positions 1 and 4.	1.98	1	0	aromatic amine; benzotriazines; N-oxide	antibacterial agent; antineoplastic agent; apoptosis inducer
ver 52296 luminespib : A monocarboxylic acid amide obtained by formal condensation of the carboxy group of 5-(2,4-dihydroxy-5-isopropylphenyl)-4-[4-(morpholin-4-ylmethyl)phenyl]-1,2-oxazole-3-carboxylic acid with the amino group of ethylamine.	2.13	1	0	aromatic amide; isoxazoles; monocarboxylic acid amide; morpholines; resorcinols	angiogenesis inhibitor; antineoplastic agent; Hsp90 inhibitor
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.	2.4	2	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.	1.99	1	0
phenanthrenes Phenanthrenes: POLYCYCLIC AROMATIC HYDROCARBONS composed of three fused BENZENE rings.. phenanthrenes : Any benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof.	3.39	7	0

Condition	Relationship Strength	Studies
Bilirubinemia [description not available]	2.92	1
Benign Neoplasms [description not available]	4.52	5
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	4.52	5
Hepatocellular Carcinoma [description not available]	3.7	10
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	3.7	10
Koch's Disease [description not available]	2.03	1
Tuberculosis Any of the infectious diseases of man and other animals caused by species of MYCOBACTERIUM TUBERCULOSIS.	2.03	1
Breast Cancer [description not available]	4.32	19
Breast Neoplasms Tumors or cancer of the human BREAST.	4.32	19
Cancer of Colon [description not available]	2.79	3
Colonic Neoplasms Tumors or cancer of the COLON.	2.79	3
Encephalitis, Venezuelan Equine [description not available]	2.1	1
Experimental Neoplasms [description not available]	3.36	7
Acute Liver Injury, Drug-Induced [description not available]	2.81	3
Chemical and Drug Induced Liver Injury A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.	2.81	3
Diseases of Immune System [description not available]	3.17	1
Immune System Diseases Disorders caused by abnormal or absent immunologic mechanisms, whether humoral, cell-mediated, or both.	3.17	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	3.32	6
Age-Related Osteoporosis [description not available]	2.25	1
Osteoporosis Reduction of bone mass without alteration in the composition of bone, leading to fractures. Primary osteoporosis can be of two major types: postmenopausal osteoporosis (OSTEOPOROSIS, POSTMENOPAUSAL) and age-related or senile osteoporosis.	2.25	1
Tuberculosis, Drug-Resistant [description not available]	2.25	1
Tuberculosis, Multidrug-Resistant Tuberculosis resistant to chemotherapy with two or more ANTITUBERCULAR AGENTS, including at least ISONIAZID and RIFAMPICIN. The problem of resistance is particularly troublesome in tuberculous OPPORTUNISTIC INFECTIONS associated with HIV INFECTIONS. It requires the use of second line drugs which are more toxic than the first line regimens. TB with isolates that have developed further resistance to at least three of the six classes of second line drugs is defined as EXTENSIVELY DRUG-RESISTANT TUBERCULOSIS.	2.25	1
Gout Metabolic disorder characterized by recurrent acute arthritis, hyperuricemia and deposition of sodium urate in and around the joints, sometimes with formation of URIC ACID calculi.	2.72	2
Hyperuricemia Excessive URIC ACID or urate in blood as defined by its solubility in plasma at 37 degrees C; greater than 0.42mmol per liter (7.0mg/dL) in men or 0.36mmol per liter (6.0mg/dL) in women. This condition is caused by overproduction of uric acid or impaired renal clearance. Hyperuricemia can be acquired, drug-induced or genetically determined (LESCH-NYHAN SYNDROME). It is associated with HYPERTENSION and GOUT.	2.72	2
Cancer of Stomach [description not available]	2.31	1
Stomach Neoplasms Tumors or cancer of the STOMACH.	2.31	1
Cancer of Prostate [description not available]	2.8	3
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	2.8	3
Enterovirus Infections Diseases caused by ENTEROVIRUS.	2.41	1
Hepatitis B Virus Infection [description not available]	2.41	1
Cancer of Liver [description not available]	3.7	10
Hepatitis B INFLAMMATION of the LIVER in humans caused by a member of the ORTHOHEPADNAVIRUS genus, HEPATITIS B VIRUS. It is primarily transmitted by parenteral exposure, such as transfusion of contaminated blood or blood products, but can also be transmitted via sexual or intimate personal contact.	2.41	1
Liver Neoplasms Tumors or cancer of the LIVER.	3.7	10
Fatty Liver, Nonalcoholic [description not available]	2.21	1
Insulin Sensitivity [description not available]	2.21	1
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.	2.21	1
Non-alcoholic Fatty Liver Disease Fatty liver finding without excessive ALCOHOL CONSUMPTION.	7.21	1
Acute Onset Vascular Dementia [description not available]	2.25	1
Dementia, Vascular An imprecise term referring to dementia associated with CEREBROVASCULAR DISORDERS, including CEREBRAL INFARCTION (single or multiple), and conditions associated with chronic BRAIN ISCHEMIA. Diffuse, cortical, and subcortical subtypes have been described. (From Gerontol Geriatr 1998 Feb;31(1):36-44)	2.25	1
Liver Steatosis [description not available]	2.54	2
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.	2.54	2
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).	3.02	4
Carcinoma, Small Cell Lung [description not available]	2.21	1
Cancer of Lung [description not available]	3.08	5
Lung Neoplasms Tumors or cancer of the LUNG.	3.08	5
Small Cell Lung Carcinoma A form of highly malignant lung cancer that is composed of small ovoid cells (SMALL CELL CARCINOMA).	2.21	1
Asthma, Bronchial [description not available]	2.1	1
Eosinophilia, Pulmonary [description not available]	2.1	1
Asthma A form of bronchial disorder with three distinct components: airway hyper-responsiveness (RESPIRATORY HYPERSENSITIVITY), airway INFLAMMATION, and intermittent AIRWAY OBSTRUCTION. It is characterized by spasmodic contraction of airway smooth muscle, WHEEZING, and dyspnea (DYSPNEA, PAROXYSMAL).	2.1	1
Pulmonary Eosinophilia A condition characterized by infiltration of the lung with EOSINOPHILS due to inflammation or other disease processes. Major eosinophilic lung diseases are the eosinophilic pneumonias caused by infections, allergens, or toxic agents.	2.1	1
Uremia A clinical syndrome associated with the retention of renal waste products or uremic toxins in the blood. It is usually the result of RENAL INSUFFICIENCY. Most uremic toxins are end products of protein or nitrogen CATABOLISM, such as UREA or CREATININE. Severe uremia can lead to multiple organ dysfunctions with a constellation of symptoms.	2.1	1
Alloxan Diabetes [description not available]	2.13	1
Diabetic Glomerulosclerosis [description not available]	2.13	1
Diabetic Nephropathies KIDNEY injuries associated with diabetes mellitus and affecting KIDNEY GLOMERULUS; ARTERIOLES; KIDNEY TUBULES; and the interstitium. Clinical signs include persistent PROTEINURIA, from microalbuminuria progressing to ALBUMINURIA of greater than 300 mg/24 h, leading to reduced GLOMERULAR FILTRATION RATE and END-STAGE RENAL DISEASE.	2.13	1
Cleft Palate, Isolated [description not available]	2.15	1
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.	2.15	1
Cleft Palate Congenital fissure of the soft and/or hard palate, due to faulty fusion.	2.15	1
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	4.05	15
Anasarca [description not available]	2.13	1
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	2.13	1
Fish Diseases Diseases of freshwater, marine, hatchery or aquarium fish. This term includes diseases of both teleosts (true fish) and elasmobranchs (sharks, rays and skates).	2.44	2
Rheumatoid Arthritis [description not available]	2.04	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.	2.04	1
Chylopericardium [description not available]	2.05	1
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.	2.05	1
Chromosome-Defective Micronuclei [description not available]	2.45	2
Cell Transformation, Neoplastic Cell changes manifested by escape from control mechanisms, increased growth potential, alterations in the cell surface, karyotypic abnormalities, morphological and biochemical deviations from the norm, and other attributes conferring the ability to invade, metastasize, and kill.	3.24	6
Hormone-Dependent Neoplasms [description not available]	2.05	1
Experimental Mammary Neoplasms [description not available]	2.92	4
Granulocytic Leukemia [description not available]	2.05	1
Acute Disease Disease having a short and relatively severe course.	2.05	1
Leukemia, Myeloid Form of leukemia characterized by an uncontrolled proliferation of the myeloid lineage and their precursors (MYELOID PROGENITOR CELLS) in the bone marrow and other sites.	2.05	1
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	2.73	3
Experimental Hepatoma [description not available]	5.15	18
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.	2.06	1
Innate Inflammatory Response [description not available]	2.06	1
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	2.06	1
Colitis Gravis [description not available]	2.06	1
Colitis, Ulcerative Inflammation of the COLON that is predominantly confined to the MUCOSA. Its major symptoms include DIARRHEA, rectal BLEEDING, the passage of MUCUS, and ABDOMINAL PAIN.	2.06	1
Weight Gain Increase in BODY WEIGHT over existing weight.	2.07	1
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.	2.07	1
Hepatitis, Viral, Non-A, Non-B, Parenterally-Transmitted [description not available]	2.07	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.	2.07	1
Kahler Disease [description not available]	2.07	1
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.	2.07	1
Adenocarcinoma, Basal Cell [description not available]	2.01	1
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	2.01	1
Metastase [description not available]	2.02	1
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	2.02	1
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)	2.02	1
Infections, Listeria [description not available]	2.02	1
Cocarcinogenesis The combination of two or more different factors in the production of cancer.	3.23	6
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)	2.41	2
Arachnoidal Cerebellar Sarcoma, Circumscribed [description not available]	2.03	1
Medulloblastoma A malignant neoplasm that may be classified either as a glioma or as a primitive neuroectodermal tumor of childhood (see NEUROECTODERMAL TUMOR, PRIMITIVE). The tumor occurs most frequently in the first decade of life with the most typical location being the cerebellar vermis. Histologic features include a high degree of cellularity, frequent mitotic figures, and a tendency for the cells to organize into sheets or form rosettes. Medulloblastoma have a high propensity to spread throughout the craniospinal intradural axis. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2060-1)	2.03	1
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)	2.03	1
Carcinoma, Anaplastic [description not available]	2.03	1
Carcinoma A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.	2.03	1
Cancer of Kidney [description not available]	2.66	3
Kidney Neoplasms Tumors or cancers of the KIDNEY.	2.66	3
Papilloma, Squamous Cell [description not available]	2.37	2
Cancer of Skin [description not available]	3.21	6
Papilloma A circumscribed benign epithelial tumor projecting from the surrounding surface; more precisely, a benign epithelial neoplasm consisting of villous or arborescent outgrowths of fibrovascular stroma covered by neoplastic cells. (Stedman, 25th ed)	2.37	2
Skin Neoplasms Tumors or cancer of the SKIN.	3.21	6
Palmoplantaris Pustulosis [description not available]	1.96	1
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.	1.96	1
Aura [description not available]	1.96	1
Epilepsy A disorder characterized by recurrent episodes of paroxysmal brain dysfunction due to a sudden, disorderly, and excessive neuronal discharge. Epilepsy classification systems are generally based upon: (1) clinical features of the seizure episodes (e.g., motor seizure), (2) etiology (e.g., post-traumatic), (3) anatomic site of seizure origin (e.g., frontal lobe seizure), (4) tendency to spread to other structures in the brain, and (5) temporal patterns (e.g., nocturnal epilepsy). (From Adams et al., Principles of Neurology, 6th ed, p313)	1.96	1
African Lymphoma [description not available]	1.96	1
Burkitt Lymphoma A form of undifferentiated malignant LYMPHOMA usually found in central Africa, but also reported in other parts of the world. It is commonly manifested as a large osteolytic lesion in the jaw or as an abdominal mass. B-cell antigens are expressed on the immature cells that make up the tumor in virtually all cases of Burkitt lymphoma. The Epstein-Barr virus (HERPESVIRUS 4, HUMAN) has been isolated from Burkitt lymphoma cases in Africa and it is implicated as the causative agent in these cases; however, most non-African cases are EBV-negative.	1.96	1
Abnormalities, Multiple Congenital abnormalities that affect more than one organ or body structure.	1.95	1
Spider Veins [description not available]	1.95	1
Telangiectasis Permanent dilation of preexisting blood vessels (CAPILLARIES; ARTERIOLES; VENULES) creating small focal red lesions, most commonly in the skin or mucous membranes. It is characterized by the prominence of skin blood vessels, such as vascular spiders.	1.95	1
Nicotine Addiction [description not available]	1.96	1
Tobacco Use Disorder Tobacco used to the detriment of a person's health or social functioning. Tobacco dependence is included.	1.96	1
Anemia, Hypoplastic [description not available]	1.95	1
Bone Marrow Diseases Diseases involving the BONE MARROW.	1.95	1
Anemia, Aplastic A form of anemia in which the bone marrow fails to produce adequate numbers of peripheral blood elements.	1.95	1
Fibroid [description not available]	1.98	1
Cancer of the Uterus [description not available]	1.98	1
Leiomyoma A benign tumor derived from smooth muscle tissue, also known as a fibroid tumor. They rarely occur outside of the UTERUS and the GASTROINTESTINAL TRACT but can occur in the SKIN and SUBCUTANEOUS TISSUE, probably arising from the smooth muscle of small blood vessels in these tissues.	1.98	1
Uterine Neoplasms Tumors or cancer of the UTERUS.	1.98	1
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	1.98	1
Kaposi Disease [description not available]	1.98	1
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.	1.98	1
Muscle Relaxation That phase of a muscle twitch during which a muscle returns to a resting position.	2	1
Allergic Reaction [description not available]	2	1
Hypersensitivity Altered reactivity to an antigen, which can result in pathologic reactions upon subsequent exposure to that particular antigen.	2	1
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
Germinoblastoma [description not available]	2.01	1
Lymphoma A general term for various neoplastic diseases of the lymphoid tissue.	2.01	1
Malignant Melanoma [description not available]	1.95	1
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)	1.95	1
Allergy, Drug [description not available]	1.97	1
Delayed Hypersensitivity [description not available]	1.97	1
Drug Hypersensitivity Immunologically mediated adverse reactions to medicinal substances used legally or illegally.	1.97	1
Adenoma, Basal Cell [description not available]	1.96	1
Delayed Effects, Prenatal Exposure [description not available]	1.96	1
Adenoma A benign epithelial tumor with a glandular organization.	1.96	1
Porphyria [description not available]	2.37	2
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.	2.37	2
Leukemia, Lymphocytic [description not available]	1.97	1
Leukemia, Lymphoid Leukemia associated with HYPERPLASIA of the lymphoid tissues and increased numbers of circulating malignant LYMPHOCYTES and lymphoblasts.	1.97	1
Abnormalities, Autosome [description not available]	1.97	1

alpha-naphthoflavone

Description

Cross-References

Synonyms (70)

Research Excerpts

Toxicity

Pharmacokinetics

Bioavailability

Dosage Studied

Roles (3)

Drug Classes (3)

Protein Targets (66)

Potency Measurements

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Other Measurements

Biological Processes (306)

Molecular Functions (108)

Ceullar Components (53)

Bioassays (273)

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Studies (638)

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Research Demand Index: 23.80

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alpha-naphthoflavone

Description

Cross-References

Synonyms (70)

Research Excerpts

Toxicity

Pharmacokinetics

Bioavailability

Dosage Studied

Roles (3)

Drug Classes (3)

Protein Targets (66)

Potency Measurements

Inhibition Measurements

Activation Measurements

Other Measurements

Biological Processes (306)

Molecular Functions (108)

Ceullar Components (53)

Bioassays (273)

Research

Studies (638)

Market Indicators

Research Demand Index: 23.80

Study Types

Related Drugs (1,004)

Related Conditions (144)