taurocholic acid profile

Taurocholic acid is a bile acid synthesized in the liver from cholesterol. It is conjugated with taurine, an amino acid, and plays a crucial role in the digestion and absorption of fats. It is a primary bile acid, meaning it is directly synthesized by the liver, and it acts as a detergent in the small intestine, emulsifying dietary fats and facilitating their breakdown by enzymes. Taurocholic acid is studied extensively to understand its role in liver health, digestive processes, and the development of gallstones. It is also being investigated for its potential therapeutic applications in conditions such as obesity, diabetes, and cancer.'

Taurocholic Acid: The product of conjugation of cholic acid with taurine. Its sodium salt is the chief ingredient of the bile of carnivorous animals. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and cholerectic. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

taurocholate : An organosulfonate oxoanion that is the conjugate base of taurocholic acid. [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]

taurocholic acid : A bile acid taurine conjugate of cholic acid that usually occurs as the sodium salt of bile in mammals. [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	6675
CHEMBL ID	224867
CHEBI ID	28865
SCHEMBL ID	3705
MeSH ID	M0021069

Synonym
BIDD:PXR0195
n-choloyltaurine
2-[(3alpha,7alpha,12alpha-trihydroxy-24-oxo-5beta-cholan-24-yl)amino]ethanesulfonic acid
CHEBI:28865 ,
choloyl-taurine
AB01275537-01
cholic acid taurine conjugate
wln: l e5 b666tj a1 dq e1 fy1&2vm2swq kq oq
3.alpha.,12.alpha.-trihydroxy-5.beta.-cholanic acid 24-taurine
nsc-25505
NSC25505 ,
cholaic acid
taurine, n-choloyl-
ethanesulfonic acid,5.beta.,7.alpha.,12.alpha.)-3,7,12-trihydroxy-24-oxocholan-24-yl]amino]-
2-[(3.alpha.,12.alpha.-trihydroxy-24-oxo-5.beta.-cholan-24-yl)amino]ethanesulfonic acid
2-{[(3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxy-24-oxocholan-24-yl]amino}ethanesulfonic acid
2-[[(4r)-4-[(3r,5s,7r,8r,9s,10s,12s,13r,14s,17r)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]ethanesulfonic acid
n-(3alpha,7alpha,12alpha-trihydroxy-5beta-cholan-24-oyl)-taurine
LMST05040001
SPECTRUM5_002015
ethanesulfonic acid, 2-[[(3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxy-24-oxocholan-24-yl]amino]-
2-((3-alpha,7-alpha,12-alpha-trihydroxy-24-oxo-5-be ta-cholan-24-yl)amino)ethanesulfonic acid
ethanesulfonic acid, 2-(((3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxy-24-oxocholan-24-yl)amino)-
2-(((3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxy-24-oxocholan-24-yl)amino)ethanesulfonic acid
3alpha,7alpha,12alpha-trihydroxy-5beta-cholanic acid 24-taurine
acidum cholatauricum
taurocholate
81-24-3
cholyltaurine
taurocholic acid
DB04348
taurine cholate
einecs 201-336-2
nsc 25505
2-(((3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxy-24-oxocholan-24-yl)amino)ethanesulphonic acid
hsdb 832
T-1150
HMS2090N18
CHEMBL224867
5e090o0g3z ,
unii-5e090o0g3z
BMSE000927
3alpha,7alpha,12alpha-trihydroxy-5beta-cholan-24-oic acid n-(2-sulfoethyl)amide
bdbm50375594
gtpl4547
[3h]-taurocholate
[3h]taurocholic acid
gtpl4546
[3h]-taurocholic acid
2-[(4r)-4-[(1s,2s,5r,7s,9r,10r,11s,14r,15r,16s)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid
ethanesulfonic acid, 2-[[(3.alpha.,5.beta.,7.alpha.,12.alpha.)-3,7,12-trihydroxy-24-oxocholan-24-yl]amino]-
SCHEMBL3705
taurocholic acid [mi]
taurocholic acid [hsdb]
2-(((3.alpha.,5.beta.,7.alpha.,12.alpha.)-3,7,12-trihydroxy-24-oxocholan-24-yl)amino)ethanesulfonic acid
3.beta.-hydroxydinor-5-cholenic acid
AKOS030242840
sr-05000001533
SR-05000001533-1
3a,7a,12a-trihydroxy-5b-cholanic acid-24-taurine
2-{[(3beta,5beta,7alpha,12alpha,14beta,17alpha)-3,7,12-trihydroxy-24-oxocholan-24-yl]amino}ethanesulfonic acid
Q2659931
CS-0013819
HY-B1788
MS-29575
DTXSID00883259
2-[(4r)-4-[(1r,3as,3br,4r,5as,7r,9as,9bs,11s,11ar)-4,7,11-trihydroxy-9a,11a-dimethyl-hexadecahydro-1h-cyclopenta[a]phenanthren-1-yl]pentanamido]ethane-1-sulfonic acid
EN300-19734139

Excerpt	Reference	Relevance
"Taurocholic acid is a primary bile acid that promotes digestion, absorption, and excretion of dietary lipids."	( Sodium taurocholate hydrate inhibits influenza virus replication and suppresses influenza a Virus-triggered inflammation in vitro and in vivo. Hu, X; Jin, M; Sun, X; Yang, L; Zhang, Q; Zhao, L, 2023)	1.63

Excerpt	Reference	Relevance
"The influence of mixtures of taurocholate (TC), oleic acid (OA), caprylic acid (CA), and monolein (MO) on the toxic effects of deoxycholate (DC) in rat jejunum have been investigated using both a closed loop and perfusion technique."	( Influence of mixtures of taurocholate, fatty acids, and monolein on the toxic effects of deoxycholate in rat jejunum in vivo. Guiraldes, E; Harries, JT; Lamabadusuriya, SP, 1975)	0.25
" The relative toxic potential of the drug congeners (CsG greater than CsA greater than CsH = CsF = CsA/M17) correlated well with the degree of their accumulation in the hepatocytes during exposure to equimolar drug concentrations."	( In vitro toxicity assessment of cyclosporin A and its analogs in a primary rat hepatocyte culture model. Boelsterli, UA; Bouis, P; Brouillard, JF; Donatsch, P, 1988)	0.27
" Finally, CDCA, DCA and LagoDCA were prominent outliers being more toxic than predicted by RMw."	( Bile acid toxicity structure-activity relationships: correlations between cell viability and lipophilicity in a panel of new and known bile acids using an oesophageal cell line (HET-1A). Gilmer, JF; Keaveney, R; Kelleher, D; Long, A; Majer, F; Peta, VK; Sharma, R; Wang, J, 2010)	0.36
" Based on the analysis using principle components analysis (PCA), toxic groups could be distinguished from their control groups, which suggested that the variance of the contents of bile acids could evaluate hepatotoxicity caused by ET and DB."	( [Evaluation on hepatotoxicity caused by Dioscorea bulbifera based on analysis of bile acids]. Chen, CC; Hu, ZB; Ji, LL; Wang, JM; Wang, ZT; Xu, Y; Yang, L, 2011)	0.37
" LD50 values for LHT7 in female and male mice were 56."	( Preliminary safety evaluation of a taurocholate-conjugated low-molecular-weight heparin derivative (LHT7): a potent angiogenesis inhibitor. Alam, F; Byun, Y; Chung, SW; Hwang, SR; Kim, JY; Moon, HT; Park, J, 2015)	0.42
"Several factors are thought to be implicated in the occurrence of idiosyncratic adverse drug reactions."	( Impact of inflammation on chlorpromazine-induced cytotoxicity and cholestatic features in HepaRG cells. Abdel-Razzak, Z; Al-Attrache, H; Antherieu, S; Bachour-El Azzi, P; Guguen-Guillouzo, C; Guillouzo, A; Labbe, G; Lepage, S; Morel, I; Savary, CC; Sharanek, A, 2014)	0.4
" The preclinical studies showed the safety dose of LHT7 is less than 20 mg/kg in SD rats and in the next safety analysis in beagle dogs showed that there were no organ-specific adverse effects in higher doses, such as, 12 mg/kg."	( Safety studies on intravenous infusion of a potent angiogenesis inhibitor: taurocholate-conjugated low molecular weight heparin derivative LHT7 in preclinical models. Al-Hilal, TA; Alam, F; Byun, Y; Chung, SW; Hwang, SR; Jeon, OC; Kang, BH; Kang, MS; Kim, HS; Kim, SY; Kwon, GH; Lee, JY; Shin, SH; Zhang, HS, 2016)	0.43

Excerpt	Reference	Relevance
" The pharmacokinetics of these compounds after intravenous infusion were studied in bile-fistula dogs using both indirect and direct pharmacokinetic techniques."	( Saturation kinetics of iocetamic acid: Evaluation of indirect pharmacokinetic techniques and comparison with iopanoic acid. Barnhart, JL; Berk, RN; Loeb, PM; Staubus, AE, )	0.13
"The disposition kinetics of [3H]taurocholate ([3H]TC) in perfused normal and cholestatic rat livers were studied using the multiple indicator dilution technique and several physiologically based pharmacokinetic models."	( Hepatic pharmacokinetics of taurocholate in the normal and cholestatic rat liver. Chang, P; Hung, DY; Roberts, MS; Siebert, GA, 2005)	0.33
" For pharmacokinetic evaluation, antibiotics were subcutaneously administered at 3 hours after the pancreatitis induction."	( Pharmacokinetic and pharmacodynamic properties of biapenem, a carbapenem antibiotic, in rat experimental model of severe acute pancreatitis. Hikida, M; Ito, F; Kataoka, H; Kijima, K; Maebashi, K; Mikami, Y; Muto, Y; Niida, M; Sakakibara, S; Shimizu, A; Suzuki, K; Takata, T; Takeda, K; Unno, M, 2008)	0.35
" It was successfully applied to a pharmacokinetic study of CGA and TCA in healthy Chinese volunteers after oral administration of Shuanghua Baihe tablets (SBTs)."	( Simultaneous quantification of chlorogenic acid and taurocholic acid in human plasma by LC-MS/MS and its application to a pharmacokinetic study after oral administration of Shuanghua Baihe tablets. Cheng, ML; Ding, L; Gu, P; Liu, RJ; Liu, YJ; Ma, PC; Wu, Y; Zheng, L, 2016)	0.68

Excerpt	Reference	Relevance
"The present study evaluated the therapeutic effects of rebamipide alone and in combination with cimetidine on experimental gastritis established by the administration of 5 mM sodium taurocholate (TCA) for 6 months in rats."	( Therapeutic effects of oral rebamipide and in combination with cimetidine on experimental gastritis in rats. Fujimura, J; Haruma, K; Kajiyama, G; Kishimoto, S; Kobayashi, H; Machino, H; Sakurai, K; Shimamoto, T; Shimizu, S; Yamasaki, K, 1992)	0.28
" These occurred only in the groups given MNNG in combination with stress, aspirin, or sodium taurocholate, and did not occur in experimental groups given either MNNG, stress, aspirin, or sodium taurocholate alone, and did not occur in the control group."	( Experimental models for gastric leiomyosarcoma. The effects of N-methyl-N'-nitro-N-nitrosoguanidine in combination with stress, aspirin, or sodium taurocholate. Cohen, A; Geller, SA; Horowitz, I; Toth, LS; Werther, JL, 1984)	0.27
"Hepatic uptake carriers of the organic anion-transporting peptide (OATP) family of solute carriers are more and more recognized as being involved in hepatic elimination of many drugs and potentially associated drug-drug interactions."	( Substrate-dependent drug-drug interactions between gemfibrozil, fluvastatin and other organic anion-transporting peptide (OATP) substrates on OATP1B1, OATP2B1, and OATP1B3. Brun, ME; Funk, C; Noé, J; Portmann, R, 2007)	0.34
"The hepatic organic anion transporting polypeptides (OATPs) influence the pharmacokinetics of several drug classes and are involved in many clinical drug-drug interactions."	( Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions. Artursson, P; Haglund, U; Karlgren, M; Kimoto, E; Lai, Y; Norinder, U; Vildhede, A; Wisniewski, JR, 2012)	0.38
"The rabbits were randomly divided into 3 groups: group A without any treatment, group B with single treatment of stilamin, and group C with treatment of saizen combined with stilamin."	( Protective effects of saizen in combination with stilamin on intestinal mucosa of a rabbit model of severe acute pancreatitis. Li, B; Liu, H; Lu, Y; Xu, H; Yang, M; Yu, Y, 2013)	0.39
" Thus, application of ursodeoxycholic acid, rosuvastatin and allopurinol in these study patients with NAFLD dosages in combination with hyperuricemia improves the clinical symptoms and normalization of biochemical parameters and normalizes the spectrum of biliary acids."	( [CORRECTION OF BILE FLOW CHARACTERISTICS IN PATIENTS WITH NON-ALCOHOLIC FATTY LIVER DISEASE IN COMBINATION WITH HYPERURICEMIA]. Barabanchyk, OV; Kozak, NP; Svintsits'kyĭ, AS, 2014)	0.4

Excerpt	Reference	Relevance
" Apparent saturation kinetics were found in physiological concentrations of retinol, whereas a linear relationship between the concentration and absorption rate was found at pharmacological concentrations of retinol in the perfusate."	( Vitamin A1 intestinal absorption in vivo: influence of luminal factors on transport. Hollander, D; Muralidhara, KS, 1977)	0.26
" Increasing the sodium taurocholate concentration in the micellar infusate up to 15 mM did not increase the rate of absorption of the vitamin."	( Intestinal absorption of alpha-tocopherol in the unanesthetized rat. The influence of luminal constituents on the absorptive process. Hollander, D; Muralidhara, KS, 1977)	0.26
" When the absorption rate was plotted against the perfusate concentration, a linear relationship was found between these two parameters in the ileum and colon."	( Vitamin K2 colonic and ileal in vivo absorption: bile, fatty acids, and pH effects on transport. Hollander, D; Rim, E; Ruble, PE, 1977)	0.26
" In both the jejunum and the ileum a linear relationship was found between the absorption rate of the vitamin and its intraluminal concentration."	( Vitamin D-3 intestinal absorption in vivo: influence of fatty acids, bile salts, and perfusate pH on absorption. Hollander, D; Muralidhara, KS; Zimmerman, A, 1978)	0.26
" Absorption rate of 25-OH-D3 increased as the pH, the bile acid concentration, and thickness of the unstirred water layer were decreased."	( Intestinal absorption of 25-hydroxyvitamin D3 in unanesthetized rat. Hollander, D; Morgan, D; Rim, E, 1979)	0.26
" At low concentrations (42-1260 microM), the relationship between linoleic acid concentration and its absorption rate fitted best to a rectangular hyperbola."	( A dual, concentration-dependent absorption mechanism of linoleic acid by rat jejunum in vitro. Chow, SL; Hollander, D, 1979)	0.26
" To find whether the watery diarrhoea was due to bile acid malabsorption, the absorption rate of [14C]-taurocholic acid was measured in untreated rats and rats treated with lincomycin using an in vivo perfusion technique."	( The mechanism of lincomycin-induced diarrhoea. Andersen, KJ; Hoff, SG; Schjonsby, H, 1977)	0.47
"When Rats were fed a lactose containing diet, both the absorption rate of sodium taurocholate at the level of ileum and the contents of bile acids of the small intestine were increased."	( [The effect of dietary lactose on the ileal absorption of sodium taurocholate in rats]. Leprince, C; Méjean, C; Riottot, M; Sacquet, E, 1977)	0.26
" The rate of absorption decreased from the colon to the duodenum (colon greater than ileum greater than jejunum greater than duodenum)."	( Intestinal oxalate absorption. I. Absorption in vitro. Caspary, WF, 1977)	0.26
" The plot of absorption rate vs."	( Arachidonic acid intestinal absorption: mechanism of transport and influence of luminal factors of absorption in vitro. Chow, SL; Hollander, D, 1978)	0.26
" At other fatty acid concentrations, the fractional rate of absorption of the bile acid was much lower than that of the fatty acid."	( The effect of lipids on taurocholate absorption from intestinal loops in the rat. Budowski, P; Sklan, D, 1977)	0.26
" Increasing the bile salt concentration to 20 mM or the addition of long chain fatty acids, monoolein, or lecithin all resulted in significant (P less than 0-05) decrease in the absorption rate of the vitamin."	( Factors affecting the absorption of vitamin K-1 in vitro. Hollander, D; Rim, E, 1976)	0.26
" The percent absolute bioavailability of the compound was enhanced from 3-6% (PEG 400 solution) to 15-27% when the emulsion formulations were used."	( Enhancement of nasal delivery of a renin inhibitor in the rat using emulsion formulations. Baron, DA; Belonio, B; Kararli, TT; Katz, B; Needham, TE; Schmidt, RE; Schoenhard, G, 1992)	0.28
" Cholylsarcosine was shown to be well absorbed from the ileum but underwent little absorption from the jejunum or colon."	( Transport, metabolism, and effect of chronic feeding of cholylsarcosine, a conjugated bile acid resistant to deconjugation and dehydroxylation. Angellotti, MA; Hofmann, AF; Marcus, SN; Rossi, SS; Schmassmann, A; Schteingart, CD; Ton-Nu, HT, 1990)	0.28
" It is well established that digitalis compounds present great variability in their respective "in vivo" bioavailability in human (60-90% for digoxin, 0% for ouabain)."	( Intestinal absorption of drugs: digitalis binding and transport by brush-border membrane vesicles from human duodenum. Coppens, R; Di Marino, V; Durand, A; Masset, D; Placidi, M; Rahmani, R; Rahmani-Jourdheuil, D, 1991)	0.28
" Concentrations of TC above the critical micelle concentration (CMC) did not affect the absorption rate of the hydrophilic drugs PA and TP; the barrier function of the intestinal wall for PA and TP was not altered in the presence of taurocholate."	( Intestinal absorption of drugs. III. The influence of taurocholate on the disappearance kinetics of hydrophilic and lipophilic drugs from the small intestine of the rat. Breäs, R; Poelma, FG; Tukker, JJ, 1990)	0.28
" Compound 1 at a concentration of 10 mM in the perfusate induced a twofold reduction of the absorption rate compared with the same concentration of 2 in saline."	( Intestinal absorption of drugs. I: The influence of taurocholate on the absorption of dantrolene in the small intestine of the rat. Crommelin, DJ; Poelma, FG; Tukker, JJ, 1989)	0.28
" Plasma elimination half-lives but not absorption rate constants for [14C]TC (10 mumol/kg) were about two-fold reduced in 18 as compared to 10 or 14 degrees C acclimated fish."	( Biliary excretion of [14C]taurocholate by rainbow trout (Salmo gairdneri) is stimulated at warmer acclimation temperature. Curtis, LR; Kemp, CJ; Svec, AV, 1986)	0.27
"We studied the characteristics and mechanisms of MNNG (N-methyl-N'-nitro-N-nitrosoguanidine) intestinal absorption and the interaction between bile acids and fatty acids and MNNG absorption rate in vivo in male Sprague-Dawley rats."	( The mechanisms of intestinal absorption of the carcinogen MNNG (N-methyl-N'-nitro-N-nitrosoguanidine). Dadufalza, V; Hollander, D; Koyama, SY, 1988)	0.27
" Therefore, the two-dimensional laminar flow model is shown to be valid not only for determining the kinetic parameters of a carrier-mediated transport in situ but also for predicting the absorption rate in situ from the uptake rate in vitro."	( Determination of kinetic parameters of a carrier-mediated transport in the perfused intestine by two-dimensional laminar flow model: effects of the unstirred water layer. Hanano, M; Iga, T; Miyamoto, Y; Yuasa, H, 1986)	0.27
" The absorption rate of sodium taurocholate, 25 mmol/l, was determined in vivo in jejunal or ileal segments."	( Increase in the ileal absorption rate of sodium taurocholate in germ-free or conventional rats given an amylomaize-starch diet. Riottot, M; Sacquet, E, 1985)	0.27
" At 9 mM, taurocholic acid was absorbed from the pouches at a mean rate of 1,150 +/- 115 nmol/min in contrast to an absorption rate of 225 +/- 10 nmol/min for sodium taurocholate at the same concentration."	( Bile acid and bile salt disrupt gastric mucosal barrier in the dog by different mechanisms. Duane, WC; Sievert, CE; Wiegand, DM, 1982)	0.67
"3%) and taurocholate absorption rate decreased with age (14 days, 941."	( Passive jejunal bile salt absorption alters the enterohepatic circulation in immature rats. Fayer, JC; Mascarenhas, MR; Shiau, YF; Stahl, GE; Watkins, JB, 1993)	0.29
"In the guinea pig, ingestion of a taurocholate-enriched diet resulted in a 75% decrease in the absorption rate of ursodeoxycholyltaurine."	( Negative feedback regulation of the ileal bile acid transport system in rodents. Crombie, DL; Hagey, LR; Hofmann, AF; Lillienau, J; Longmire-Cook, SJ; Munoz, J, 1993)	0.29
" Given the known hypocholesterolemic and antiatherosclerotic properties of some steroid glycosides, we synthesized a series of sterol derivatives by coupling some phytosterols known to interact with sterol absorption and also to be poorly absorbed to a cationic group."	( Selection of cholesterol absorption inhibitors devoid of secondary intestinal effects. Abou el Fadil, F; Boubia, B; Descroix-Vagne, M; Guffroy, C; Marquet, F; Pansu, D, )	0.13
"The objective was to investigate the ability of a glycosteroid (TC002) to increase the oral bioavailability of gentamicin."	( Intestinal transport of gentamicin with a novel, glycosteroid drug transport agent. Amidon, GL; Axelrod, HR; Choe, S; Hui, YW; Kakarla, R; Kim, JS; Lipka, E; Longley, CB; Sofia, MJ; Weber, SJ, 1998)	0.3
" Bioavailability of gentamicin was determined by HPLC."	( Intestinal transport of gentamicin with a novel, glycosteroid drug transport agent. Amidon, GL; Axelrod, HR; Choe, S; Hui, YW; Kakarla, R; Kim, JS; Lipka, E; Longley, CB; Sofia, MJ; Weber, SJ, 1998)	0.3
"The bioavailability of gentamicin was substantially increased in the presence of TC002 in both rats and dogs."	( Intestinal transport of gentamicin with a novel, glycosteroid drug transport agent. Amidon, GL; Axelrod, HR; Choe, S; Hui, YW; Kakarla, R; Kim, JS; Lipka, E; Longley, CB; Sofia, MJ; Weber, SJ, 1998)	0.3
" White the passive absorption rate constants (kf, h-1) determined in colon in the presence of increasing lauryl sulfate concentrations showed an asymptotic value about 7-fold higher than that of cefadroxil alone, only a 2-fold higher value was obtained in the presence of taurocholate at similar concentrations."	( Experimental studies on the influence of surfactants on intestinal absorption of drugs. Cefadroxil as model drug and sodium taurocholate as natural model surfactant: studies in rat colon and in rat duodenum. Carmona-Ibáñez, G; del Val Bermejo-Sanz, M; Martín-Villodre, A; Rius-Alarcó, F, 1999)	0.3
" NT also facilitated transcellular uptake of (3)H-glucose and (3)H-leucine and increased paracellular uptake to (51)Cr-EDTA and (3)H-mannitol, but did not alter the absorption rate for (14)C-antipyrine."	( Enhancement of jejunal absorption of conjugated bile acid by neurotensin in rats. Carraway, RE; Gui, X, 2001)	0.31
" The absorption rate of taurocholic acid was almost 100%, 56%, and 23% in the JD, CeD, and the CoD group, respectively."	( Effects of internal biliary bypass on the regulation of hepatic cholesterol 7alpha-hydroxylase activity in rats. Chijiiwa, K; Kuroki, S; Mizuta, A; Nakamura, K; Tanaka, M, 2001)	0.62
" The absolute bioavailability of insulin when given as a nebulized solution (0."	( Mechanisms for absorption enhancement of inhaled insulin by sodium taurocholate. Eirefelt, S; Hjertberg, E; Hultkvist Bengtsson, U; Johansson, F; Tronde, A, 2002)	0.31
" After oral administration the extent of bioavailability compared with intra-muscular administration is low, due to a first pass effect."	( Buccal delivery of thiocolchicoside: in vitro and in vivo permeation studies. Artusi, M; Colombo, P; Junginger, HE; Santi, P, 2003)	0.32
"To develop a simple and cost-effective bioavailability test for sediment-bound contaminants, the solubilization strengths of mixtures of four commercially available surfactants and four proteins were compared to that of digestive fluids from a deposit-feeding benthic polychaete Arenicola marina."	( Commercially available chemicals that mimic a deposit feeder's (Arenicola marina) digestive solubilization of lipids. Mayer, LM; Voparil, IM, 2004)	0.32
" The use of 8 mmol x L(-1)/dose sodium taurocholate and 10 mmol x L(-1)/dose sodium deoxycholate could be able to potentially improve the bioavailability of insulin by pulmonary route."	( Deposition of insulin powders for inhalation in vitro and pharmacodynamic evaluation of absorption promoters in rats. Yang, DB; Zhang, XS; Zhu, H; Zhu, JB, 2005)	0.33
"7 h), and increased bioavailability (+13%; +44%) and dose-adjusted Cmax (+54%; +103%)."	( Effects of sodium taurocholate on the absorption of inhaled 99mTc-DTPA. Bengtsson, T; Bondesson, E; Nilsson, LE; Wollmer, P, 2006)	0.33
" LHD was pre-formulated with dimethyl sulfoxide (DMSO) as solubilizer to further improve its oral bioavailability (9."	( Absorption study of deoxycholic acid-heparin conjugate as a new form of oral anti-coagulant. Byun, Y; Kim, CY; Kim, SK; Lee, DY; Lee, E; Lee, YK; Moon, HT, 2007)	0.34
" Absorption rate constants were determined by the plot of log remaining amount of drug in perfusate vs."	( Absorptive profile of chlorogenic acid in rats. Chen, Z; Jiang, X; Li, C; Li, K; Ma, G; Ren, J, 2007)	0.34
" bioavailability in preclinical species and humans."	( Involvement of intestinal uptake transporters in the absorption of azithromycin and clarithromycin in the rat. Davis, CB; Dawson, PA; Garver, E; Han, C; Hugger, ED; Rao, A; Shearn, SP, 2008)	0.35
"The macrolide antibiotics azithromycin and clarithromycin are large molecular weight compounds that exhibit moderate to excellent oral bioavailability in preclinical species and humans."	( Interaction of macrolide antibiotics with intestinally expressed human and rat organic anion-transporting polypeptides. Davis, CB; Dawson, PA; Garver, E; Han, C; Haywood, J; Lan, T; Rao, A, 2009)	0.35
" Moreover, the bioavailability of fexofenadine x HCl after nasal administration of the microsphere formulation to rabbits was increased up to about 48% while that of the control solution was only about 3%."	( Preparation and evaluation of spray-dried hyaluronic acid microspheres for intranasal delivery of fexofenadine hydrochloride. Cho, HJ; Choi, MK; Chung, SJ; Huh, Y; Kim, DD; Kim, JS; Oh, E; Shim, CK; Yoon, IS, 2010)	0.36
" Food components and dosing time significantly altered the oral pharmacokinetics of nifedipine in rats, implying that the altered bioavailability and higher plasma concentrations in the morning time may influence dosing regimens of nifedipine for hypertension patients."	( Effect of food components and dosing times on the oral pharmacokinetics of nifedipine in rats. Cao, QR; Cui, JH; Han, HK; Lee, BJ; Lee, J; Oh, KT; Park, I; Park, JB, 2010)	0.36
"Colestyramine and colestipol are generally effective treatments of gastrointestinal symptoms from BAM, but may be poorly tolerated and reduce the bioavailability of co-administered agents."	( Systematic review: the management of chronic diarrhoea due to bile acid malabsorption. Green, J; Turner, J; Wilcox, C, 2014)	0.4
" At the concentrations of 20 to 80 microg x mL(-1), the difference of absorption rate constants (K(a)) was not statistically significant."	( [Enhancers on the transmembrane transport of chlorogenic acid]. Deng, SQ; Jiang, XH; Ren, J; Wang, LL; Xiao, Y, 2014)	0.4
" The resulting LHTD4/DCK complex showed significantly enhanced oral bioavailability (34."	( Oral delivery of a potent anti-angiogenic heparin conjugate by chemical conjugation and physical complexation using deoxycholic acid. Al-Hilal, TA; Alam, F; Byun, Y; Chung, SW; Kim, HS; Kim, SY; Mahmud, F; Seo, D, 2014)	0.4
" While DDM led to a 20-fold increase in FD4 bioavailability when it was applied in TM, no significant permeation enhancement was seen in FaSSIFmod/FeSSIFmod6."	( Interaction with Mixed Micelles in the Intestine Attenuates the Permeation Enhancing Potential of Alkyl-Maltosides. Buckley, ST; Gradauer, K; Higashino, H; Kataoka, M; Nishiumi, A; Pedersen, BL; Unrinin, K; Yamashita, S, 2015)	0.42
" PB has low bioavailability and high inter-individual variations in absorption, which limits its clinical applications."	( The effect of a tertiary bile acid, taurocholic acid, on the morphology and physical characteristics of microencapsulated probucol: potential applications in diabetes: a characterization study. Al-Salami, H; Arfuso, F; Mooranian, A; Negrulj, R, 2015)	0.69
" The bioavailability of CsA was matched and even enhanced with Precirol nanoparticles."	( Lipid nanoparticles enhance the absorption of cyclosporine A through the gastrointestinal barrier: In vitro and in vivo studies. Blanco-Prieto, MJ; Dios-Viéitez, Mdel C; Guada, M; Lana, H; Lasa-Saracíbar, B, 2016)	0.43
"Nanoparticulate drug delivery systems, mucoadhesive polymers and penetration enhancers have been used individually to overcome ocular barriers and increase bioavailability to eye tissues."	( Understanding the influence of surface properties of nanoparticles and penetration enhancers for improving bioavailability in eye tissues in vivo. Katti, DS; Mahaling, B, 2016)	0.43
" We have investigated the effect of AZD8309, a potent and orally bioavailable antagonist of the chemokine receptor CXCR2, which has been proposed to regulate the transmigration of neutrophils."	( Effect of oral administration of AZD8309, a CXCR2 antagonist, on the severity of experimental pancreatitis. D'Haese, J; Günther, A; Hansen, MB; Kärrman Mårdh, C; Lerch, MM; Mahajan, UM; Malla, SR; Mayerle, J; Sendler, M; Weiss, FU, )	0.13
" However, the implication of these mechanisms is unclear because of the low bioavailability of BBR."	( Orally Administered Berberine Modulates Hepatic Lipid Metabolism by Altering Microbial Bile Acid Metabolism and the Intestinal FXR Signaling Pathway. Aa, J; Aa, N; Cao, B; Chen, Q; Fei, F; Feng, D; Feng, S; Ge, C; Guo, GL; Guo, J; He, J; Huang, J; Kong, B; Pan, Y; Schumacher, JD; Shen, J; Sun, R; Wang, G; Wang, P; Yang, CS; Yang, N; Yu, X, 2017)	0.46
" However, hostile GI environments and nonspecific biological trafficking prevent achieving appropriate bioavailability of siRNA."	( Oral siRNA Delivery to Treat Colorectal Liver Metastases. Bae, WK; Cho, KJ; Cho, S; Kang, SH; Lee, SJ; Lee, YK; Park, IK; Revuri, V, 2017)	0.46
" Here, we used taurocholic acid (TCA) as a ligand for uptake of nanostructured lipid carriers (NLCs) mediated by a bile-acid transporter to improve oral bioavailability of curcumin (Cur)."	( Improving intestinal absorption and oral bioavailability of curcumin via taurocholic acid-modified nanostructured lipid carriers. Asghar, S; Chen, Z; Huang, L; Jin, X; Ping, Q; Tian, C; Wu, Y; Xiao, Y; Yin, L, 2017)	1.04
" Although the oral bioavailability of suspensions of its solid forms is poor, addition of vitamin E D-alpha-tocopherol polyethylene glycol 1000 succinate to dosing vehicles improves the fraction absorbed of the compound in vivo."	( Overcoming the Bile Salt-Mediated Formation of Nanocolloids That Inhibit Oral Absorption of VX-985. Bransford, P; Dworakowski, W; Kumar, S; Medek, A; Mudunuri, P; Peresypkin, A; Randles, EG; Snyder, PW; Song, B, 2019)	0.51
"The antidiabetic drug gliclazide (GLZ) has a slow absorption rate and a low bioavailability due to its poor solubility."	( Investigation of the formation of drug-drug cocrystals and coamorphous systems of the antidiabetic drug gliclazide. Aljohani, M; Erxleben, A; MacFhionnghaile, P; McArdle, P, 2019)	0.51
" In the rat model, orally administered NC-T showed an obvious hypocalcemia effect and a relative oral bioavailability of 10."	( Flash Fabrication of Orally Targeted Nanocomplexes for Improved Transport of Salmon Calcitonin across the Intestine. Chen, Y; He, S; Le, Z; Leong, KW; Liu, J; Liu, L; Liu, Z; Mao, HQ; Sun, L, 2020)	0.56
" In conclusion, STC/Soluplus SHNPs via ASBT are a potential strategy for enhancing the oral bioavailability of poorly water-soluble drugs."	( Bile acid transporter mediated STC/Soluplus self-assembled hybrid nanoparticles for enhancing the oral drug bioavailability. Cui, D; Wang, J; Wei, Q; Xiong, S; Xu, J; Zhang, S, 2020)	0.56
" STC@BBR-SANPs can help to solve the problems of poor solubility and low absorption rate of BBR in clinical use, and provide a new perspective for the future development of BBR."	( Self-Assembled nanoparticles Combining Berberine and Sodium Taurocholate for Enhanced Anti-Hyperuricemia Effect. Ai, G; Cheng, J; Huang, Z; Li, M; Li, Y; Liao, H; Qin, Z; Qu, C; Su, Z; Xie, J; Xie, Y, 2023)	0.91
"Permeability enhancer-based formulations offer a promising approach to enhance the oral bioavailability of peptides."	( Revealing the interaction between peptide drugs and permeation enhancers in the presence of intestinal bile salts. Hossain, S; Kneiszl, R; Larsson, P, 2023)	0.91

Excerpt	Relevance	Reference
"An oral dosing of either acetylsalicylic acid (ASA) or taurocholic acid (TCA) to pylorus-ligated rats subjected to water-immersion stress produced severe damage to the gastric musoca in contrast to the irritation observed in non-stressed ones."	( Effects of L-glutamine of acetylsalicylic acid or taurocholic acid-induced gastric lesions and secretory changes in pylorus-ligated rats under normal or stress conditions. Hung, CR; Okabe, S; Takagi, K; Takeuchi, K, 1976)	0.76
" They demonstrate that taurocholate synthesis is increasing rapidly during the final stages of gestation and show that cortisol augments taurocholate synthesis in a dose-response pattern."	( Synthesis of taurocholate by rat fetal liver in organ culture: effects of cortisol in vitro. Graham, TO; Lester, R; Little, JM; Van Thiel, DH, 1979)	0.26
" This procedure was repeated with varying concentrations of sodium taurocholate to obtain taurocholate dose-response tests with and without insulin."	( The effect of insulin on bile-salt-independent canalicular secretion. Jones, RS; Snow, JR, 1978)	0.26
" Dose-response inhibition of water transport in everted hamster jejunal segments was obtained with two long chain detergents (sodium dodecyl sulfate and dioctyl sodium sulfocuccinate), a fatty acid (ricinoleate), and dihydroxy bile salts (deoxycholate, chenodeoxycholate, and taurodeoxycholate), whereas no activity was seen with trihydroxy (cholate, glycocholate, and taurocholate) and tri-keto (dehydrocholate) bile salts."	( Effects of anionic surfactants on hamster small intestinal membrane structure and function: relationship to surface activity. Bass, P; Benz, L; Cline, WS; Gullikson, GW; Lorenzsonn, V; Olsen, WA, 1977)	0.26
" Female Sprague-Dawley rats were orally dosed with mirex (12."	( Mirex exposure inhibits the uptake of estradiol-17 beta(beta-D-glucuronide), taurocholate, and L-alanine into isolated rat hepatocytes. Teo, S; Vore, M, 1990)	0.28
" Male Sprague-Dawley rats were orally dosed with corn oil, mirex (50 mg/kg), or chlordecone (18."	( Mirex inhibits bile acid secretory function in vivo and in the isolated perfused rat liver. Teo, S; Vore, M, 1991)	0.28
" CR were shown to stimulate the accumulation of neutral lipids in hepatocytes in a dose-response manner."	( [Effect of chylomicron remnants on cholesterol metabolism in cultured rabbit hepatocytes: production of very low density lipoproteins and bile acids]. Kosykh, VA; Novikov, DK; Podrez, EA; Repin, VS; Trakht, IN, 1990)	0.28
" Only bile, but not secretin intravenously, both applied in a dosage equivalent with respect to their hydrokinetic action, caused a significant increase of enzyme output and enzyme concentration as well."	( Na-taurodeoxycholate acts as a specific intestinal stimulus of exocrine pancreatic secretion in man. Danzl, C; Fiedler, F; Hempen, I; Hotz, E; Lehnert, P; Mitra, H; Riepl, R, 1987)	0.27
"We have used quantitative lectin histochemistry to study the cellular binding of peanut agglutinin (PNA) and soybean agglutinin (SBA) at the rat gastric corpus mucosa that has been injured experimentally by either ethanol or sodium-taurocholate and was protected by pretreatment of a cytoprotective dosage of the natural prostaglandin E2 (PGE2)."	( Light microscopic quantitative investigation on the effects of prostaglandin E2 (PGE2) on the lectin binding pattern in rat gastric mucosa injured by ethanol or sodium taurocholate. Fringes, B; Klein, PJ; Lorenz, D; Oehlert, W, 1988)	0.27
" The log dose-response curve for E217G-induced cholestasis was much steeper and was shifted to the right in the presence of a 60 mumol/hr infusion of taurocholate."	( Taurocholate and steroid glucuronides: mutual protection against cholestasis in the isolated perfused rat liver. Durham, S; Vore, M, 1986)	0.27
" Dose-response relationships were found between the concentration of taurocholate in addition to 100 mN HCl, and delta Na+, delta H+ and sigma PD/15 min, while no differences in ED50 of taurocholate for delta Na+, delta H+ or sigma PD/15 min were observed between before and after obstructive jaundice."	( Influence of obstructive jaundice on gastric mucosal barrier in dogs. Kameyama, J; Konno, Y; Momono, S; Sasaki, I; Sato, T, 1984)	0.27
" The livers and intestines were separately perfused and dose-response curves (0."	( Hepatic uptake and intestinal absorption of bile acids in the rabbit. Aldini, R; Cerre, C; Galletti, G; Lenzi, PL; Montagnani, M; Polimeni, C; Roda, A; Roda, E, 1994)	0.29
" After dosing rats with 1 mmol/kg TRI in vivo the inhibition of uptake of CA and TC by subsequently isolated hepatocytes was not detected until 4 hr."	( Mechanism of trichloroethylene-induced elevation of individual serum bile acids. II. In vitro and in vivo interference by trichloroethylene with bile acid transport in isolated rat hepatocytes. Bai, CL; Stacey, NH, 1993)	0.29
"The therapeutic index of either taurocholate (TC) or tauroursodeoxycholate (TUDC) administration in the treatment of drug-induced cholestasis was evaluated in perfused rat liver using a dose-response study."	( Therapeutic index of taurocholate or tauroursodeoxycholate in experimental drug-induced cholestasis. Adinolfi, LE; Tripodi, MF; Utili, R, )	0.13
"Jejunal and ileal rabbit intestinal segments were separately perfused with bile acid solutions, and dose-response curves were obtained for taurocholate, ursodeoxycholate, chenodeoxycholate, deoxycholate, and their glycoconjugates."	( Intestinal absorption of bile acids in the rabbit: different transport rates in jejunum and ileum. Aldini, R; Biagi, PL; Hrelia, S; Montagnani, M; Roda, A; Roda, E, 1996)	0.29
" Kinase II inhibitor captopril or exogenous bradykinin in addition to an otherwise effective dosage of icatibant resulted in microcirculatory stasis, extensive venular leukocyte adherence, and severe histological damage."	( Inhibition of bradykinin B2 receptor preserves microcirculation in experimental pancreatitis in rats. Bloechle, C; Izbicki, JR; Knoefel, WT; Kuehn, RM; Kusterer, K; Schneider, C, 1998)	0.3
" Two dosage forms, a bioadhesive disc and a fast dissolving disc for buccal and sublingual administration of thiocolchicoside, respectively, were designed."	( Buccal delivery of thiocolchicoside: in vitro and in vivo permeation studies. Artusi, M; Colombo, P; Junginger, HE; Santi, P, 2003)	0.32
" This system is quite useful to predict the oral absorption of poorly water-soluble drugs after administration as solid dosage forms."	( In vitro system to evaluate oral absorption of poorly water-soluble drugs: simultaneous analysis on dissolution and permeation of drugs. Kataoka, M; Masaoka, Y; Sakane, T; Sezaki, H; Yamashita, S; Yamazaki, Y, 2003)	0.32
"Intragastric conditions can affect the performance of solid dosage forms."	( In vitro methods can forecast the effects of intragastric residence on dosage form performance. Digenis, G; Kalantzi, L; Nicolaides, E; Page, R; Reppas, C, 2008)	0.35
" Surprisingly, the uptake of Tac was found to be similar to that of Tol, and in both cases, the dose-response plots suggest that protein-mediated transport processes were involved."	( Alpha-tocopheryl acetate is absorbed and hydrolyzed by Caco-2 cells comparative studies with alpha-tocopherol. Ajandouz, el H; Brisson, L; Castan, S; Fontbonne, H; Nicoletti, C; Puigserver, A, 2008)	0.35
" This study used a cassette dosing approach in rat and human sandwich-cultured hepatocytes (SCH) to determine whether known or suspected hepatotoxic drugs inhibit bile acid transport individually or in combination."	( Use of cassette dosing in sandwich-cultured rat and human hepatocytes to identify drugs that inhibit bile acid transport. Brouwer, KL; Generaux, GT; Polli, JW; Vora, S; Webster, LO; Wolf, KK, 2010)	0.36
" Previous concomitant dosing studies in rats using rifamycin SV, a general organic anion-transporting polypeptide (OATP) inhibitor, suggested that the high oral absorption of azithromycin and clarithromycin may be caused by facilitative uptake by intestinal Oatps."	( Interaction of macrolide antibiotics with intestinally expressed human and rat organic anion-transporting polypeptides. Davis, CB; Dawson, PA; Garver, E; Han, C; Haywood, J; Lan, T; Rao, A, 2009)	0.35
"The present study was aimed to investigate the effect of food components and dosing time on the oral exposure of nifedipine in rats."	( Effect of food components and dosing times on the oral pharmacokinetics of nifedipine in rats. Cao, QR; Cui, JH; Han, HK; Lee, BJ; Lee, J; Oh, KT; Park, I; Park, JB, 2010)	0.36
" Forty rats were treated with procain-HCl intravenously at a dosage of 2 mg/kg body weight/h either at or 1 h after induction of pancreatitis."	( Effect of procainhydrochloride on phospholipase A2 catalytic activity in sodium taurocholate-induced acute experimental pancreatitis in rats. Kahl, S; Malfertheiner, P; Mayer, J; Nevalainen, TJ; Peuravuori, H; Pross, M; Schuette, K; Schulz, HU, 2010)	0.36
" The primary goal was to investigate the effect of cholate type, particle size and dosage of the liposomes on the hypoglycemic activity and oral bioavailability."	( Hypoglycemic activity and oral bioavailability of insulin-loaded liposomes containing bile salts in rats: the effect of cholate type, particle size and administered dose. Guan, P; Hovgaard, L; Lian, R; Lu, Y; Niu, M; Qi, J; Tan, Y; Wu, W, 2012)	0.38
" The dosage of sodium taurocholate used to induce pancreatitis was positively correlated with the degree of intestinal mucosal injury."	( Time course of intestinal barrier function injury in a sodium taurocholate-induced severe acute pancreatitis in rat model. Chen, T; Huang, Z; Liang, HY; Tang, LJ; Wang, T; Yan, HT, 2014)	0.4
" A 1000 U/kg/day dosage (three times) of EPO was administered to the EPO group."	( The effect of erythropoietin to pulmonary injury and mast cells secondary to acute pancreatitis. Firat, T; Kahramansoy, N; Kilicgun, A; Korkmaz, T, 2014)	0.4
" However, major limitations of LHT7 are its poor oral bioavailability, short half-life, and frequent parenteral dosing schedule."	( Oral delivery of a potent anti-angiogenic heparin conjugate by chemical conjugation and physical complexation using deoxycholic acid. Al-Hilal, TA; Alam, F; Byun, Y; Chung, SW; Kim, HS; Kim, SY; Mahmud, F; Seo, D, 2014)	0.4
" Based on the numerous advantages of oral administration, such as cost-effectiveness, flexible and accommodated dosing regimen, and improved compliance for patients, the ST-P123-MMs system would be evaluated as oral delivery vehicle of BC."	( In vitro and in vivo study of Baicalin-loaded mixed micelles for oral delivery. Jiao, Y; Liu, J; Yang, X; Zhai, G; Zhang, H; Zhao, L, 2016)	0.43
"Convenient multiple dosing makes oral administration an ideal route for delivery of therapeutic siRNA."	( Oral siRNA Delivery to Treat Colorectal Liver Metastases. Bae, WK; Cho, KJ; Cho, S; Kang, SH; Lee, SJ; Lee, YK; Park, IK; Revuri, V, 2017)	0.46
" Although the oral bioavailability of suspensions of its solid forms is poor, addition of vitamin E D-alpha-tocopherol polyethylene glycol 1000 succinate to dosing vehicles improves the fraction absorbed of the compound in vivo."	( Overcoming the Bile Salt-Mediated Formation of Nanocolloids That Inhibit Oral Absorption of VX-985. Bransford, P; Dworakowski, W; Kumar, S; Medek, A; Mudunuri, P; Peresypkin, A; Randles, EG; Snyder, PW; Song, B, 2019)	0.51
" Herein, a triple padlock nanocarrier prepared by a taurocholic acid-conjugated chondroitin sulfate A (TCSA) is designed to develop an oral dosage form of recombinant human teriparatide (rhPTH)."	( Oral Delivery of Parathyroid Hormone Using a Triple-Padlock Nanocarrier for Osteoporosis An, JM; Cho, S; Hwang, SR; Hwang, YH; Lee, DY; Lee, YK; Shahriar, SMS, 2021)	0.87
" These molecular-level insights can guide the design of improved permeability enhancer-based dosage forms, allowing for precise control of peptide release profiles near the intended absorption site."	( Revealing the interaction between peptide drugs and permeation enhancers in the presence of intestinal bile salts. Hossain, S; Kneiszl, R; Larsson, P, 2023)	0.91

Role	Description
human metabolite	Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
[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
bile acid taurine conjugate	A bile acid conjugate resulting from the formal condensation of a bile acid with the amino group of taurine.
amino sulfonic acid	An organosulfonic acid containing one or more amino groups.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathway	Proteins	Compounds
Bile Acid Biosynthesis	17	61
Congenital Bile Acid Synthesis Defect Type II	17	61
Congenital Bile Acid Synthesis Defect Type III	17	61
Familial Hypercholanemia (FHCA)	17	61
Zellweger Syndrome	17	61
Cerebrotendinous Xanthomatosis (CTX)	17	61
27-Hydroxylase Deficiency	17	61
3q29 copy number variation syndrome	0	12
Drug induction of bile acid pathway	0	25
Biochemical pathways: part I	0	466

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Multidrug resistance-associated protein 4	Homo sapiens (human)	IC50 (µMol)	300.0000	0.2000	5.6774	10.0000	AID681389; AID681921
Solute carrier organic anion transporter family member 1A4	Rattus norvegicus (Norway rat)	Ki	97.7000	0.0370	2.3410	7.3000	AID679492; AID681845
Solute carrier family 22 member 6	Rattus norvegicus (Norway rat)	Ki	2,770.0000	1.6000	5.7440	10.0000	AID680343
Sodium-dependent dopamine transporter	Rattus norvegicus (Norway rat)	IC50 (µMol)	6.0000	0.0007	0.9774	9.7000	AID247743
Sodium/bile acid cotransporter	Rattus norvegicus (Norway rat)	IC50 (µMol)	6.0000	6.0000	6.0000	6.0000	AID247743
Solute carrier organic anion transporter family member 1A1	Rattus norvegicus (Norway rat)	Ki	21.4000	1.1000	4.5125	9.8000	AID679969; AID679970
Solute carrier organic anion transporter family member 1A3	Rattus norvegicus (Norway rat)	Ki	183.0000	0.5000	3.3000	8.2000	AID681604
Ileal sodium/bile acid cotransporter	Homo sapiens (human)	Ki	41.5000	3.3000	6.4000	10.0000	AID681332
Sodium/bile acid cotransporter	Homo sapiens (human)	IC50 (µMol)	5.3000	1.0000	5.9267	9.6000	AID681378
Solute carrier organic anion transporter family member 1C1	Mus musculus (house mouse)	Ki	109.0000	0.2700	1.1100	2.1500	AID681369
Solute carrier family 22 member 8	Rattus norvegicus (Norway rat)	Ki	790.0000	3.0900	5.5400	9.1000	AID679290
[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)
G-protein coupled bile acid receptor 1	Homo sapiens (human)	EC50 (µMol)	4.9500	0.0237	2.5259	8.9000	AID324923
[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)
Solute carrier organic anion transporter family member 1A4	Rattus norvegicus (Norway rat)	Km	89.4000	0.2400	3.2841	6.5300	AID678788; AID679490; AID680346
Bile salt export pump	Rattus norvegicus (Norway rat)	Km	6.4500	2.2000	5.3500	7.5000	AID681721; AID681722; AID681725; AID682155
Solute carrier organic anion transporter family member 1A5	Rattus norvegicus (Norway rat)	Km	19.4225	4.3000	6.3960	8.8000	AID679480; AID681360; AID681361
ATP-binding cassette sub-family C member 3	Rattus norvegicus (Norway rat)	Km	15.9000	4.5000	4.5000	4.5000	AID679138
Solute carrier organic anion transporter family member 2B1	Homo sapiens (human)	Km	71.8000	0.7000	5.0060	8.0900	AID679476
Bile salt export pump	Homo sapiens (human)	Km	4.2500	4.2500	4.5250	4.8000	AID680937
Sodium/bile acid cotransporter	Rattus norvegicus (Norway rat)	Km	17.8000	3.7000	5.3667	7.4000	AID679118; AID681535; AID681537
Solute carrier organic anion transporter family member 1A1	Rattus norvegicus (Norway rat)	Km	36.5200	0.0150	3.4996	7.0000	AID679961; AID680238; AID680244; AID682135
Solute carrier organic anion transporter family member 1A2	Homo sapiens (human)	Km	58.2250	6.4000	7.4200	9.6000	AID1211305; AID679888; AID682037
Solute carrier organic anion transporter family member 1A3	Rattus norvegicus (Norway rat)	Km	20.7000	1.0000	4.4333	8.5000	AID679944; AID681578
Ileal sodium/bile acid cotransporter	Homo sapiens (human)	Km	18.6667	2.0000	5.3000	9.4000	AID678823; AID679687
Sodium/bile acid cotransporter	Homo sapiens (human)	Km	12.6767	6.2000	7.0500	7.9000	AID1552632; AID679561; AID679563
Solute carrier organic anion transporter family member	Bos taurus (cattle)	Km	40.2000	0.2500	0.2500	0.2500	AID1211306
Solute carrier organic anion transporter family member 4A1	Homo sapiens (human)	Km	14.9000	0.9000	0.9000	0.9000	AID678978
Solute carrier organic anion transporter family member 2B1	Rattus norvegicus (Norway rat)	Km	44.8000	0.0355	0.0355	0.0355	AID681173; AID714190
Solute carrier organic anion transporter family member 1B3	Homo sapiens (human)	Km	5.8000	0.0391	2.9388	6.4000	AID678809
Solute carrier organic anion transporter family member 1A1	Mus musculus (house mouse)	Km	12.0000	5.0000	7.1333	8.2000	AID681592
Bile salt export pump	Mus musculus (house mouse)	Km	20.6500	5.7000	5.7000	5.7000	AID679642; AID681652
Solute carrier organic anion transporter family member 1B2	Rattus norvegicus (Norway rat)	Km	17.9750	1.1000	5.2833	9.4500	AID678808; AID681648
Solute carrier organic anion transporter family member 1B1	Homo sapiens (human)	Km	17.2000	0.0076	3.2018	10.0000	AID678960; AID681342; AID681365
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
prostaglandin secretion	Multidrug resistance-associated protein 4	Homo sapiens (human)
cilium assembly	Multidrug resistance-associated protein 4	Homo sapiens (human)
platelet degranulation	Multidrug resistance-associated protein 4	Homo sapiens (human)
xenobiotic metabolic process	Multidrug resistance-associated protein 4	Homo sapiens (human)
xenobiotic transmembrane transport	Multidrug resistance-associated protein 4	Homo sapiens (human)
bile acid and bile salt transport	Multidrug resistance-associated protein 4	Homo sapiens (human)
prostaglandin transport	Multidrug resistance-associated protein 4	Homo sapiens (human)
urate transport	Multidrug resistance-associated protein 4	Homo sapiens (human)
glutathione transmembrane transport	Multidrug resistance-associated protein 4	Homo sapiens (human)
transmembrane transport	Multidrug resistance-associated protein 4	Homo sapiens (human)
cAMP transport	Multidrug resistance-associated protein 4	Homo sapiens (human)
leukotriene transport	Multidrug resistance-associated protein 4	Homo sapiens (human)
monoatomic anion transmembrane transport	Multidrug resistance-associated protein 4	Homo sapiens (human)
export across plasma membrane	Multidrug resistance-associated protein 4	Homo sapiens (human)
transport across blood-brain barrier	Multidrug resistance-associated protein 4	Homo sapiens (human)
guanine nucleotide transmembrane transport	Multidrug resistance-associated protein 4	Homo sapiens (human)
xenobiotic metabolic process	Solute carrier organic anion transporter family member 2B1	Homo sapiens (human)
monoatomic ion transport	Solute carrier organic anion transporter family member 2B1	Homo sapiens (human)
organic anion transport	Solute carrier organic anion transporter family member 2B1	Homo sapiens (human)
prostaglandin transport	Solute carrier organic anion transporter family member 2B1	Homo sapiens (human)
heme catabolic process	Solute carrier organic anion transporter family member 2B1	Homo sapiens (human)
sodium-independent organic anion transport	Solute carrier organic anion transporter family member 2B1	Homo sapiens (human)
transmembrane transport	Solute carrier organic anion transporter family member 2B1	Homo sapiens (human)
transport across blood-brain barrier	Solute carrier organic anion transporter family member 2B1	Homo sapiens (human)
bile acid and bile salt transport	Solute carrier organic anion transporter family member 2B1	Homo sapiens (human)
fatty acid metabolic process	Bile salt export pump	Homo sapiens (human)
bile acid biosynthetic process	Bile salt export pump	Homo sapiens (human)
xenobiotic metabolic process	Bile salt export pump	Homo sapiens (human)
xenobiotic transmembrane transport	Bile salt export pump	Homo sapiens (human)
response to oxidative stress	Bile salt export pump	Homo sapiens (human)
bile acid metabolic process	Bile salt export pump	Homo sapiens (human)
response to organic cyclic compound	Bile salt export pump	Homo sapiens (human)
bile acid and bile salt transport	Bile salt export pump	Homo sapiens (human)
canalicular bile acid transport	Bile salt export pump	Homo sapiens (human)
protein ubiquitination	Bile salt export pump	Homo sapiens (human)
regulation of fatty acid beta-oxidation	Bile salt export pump	Homo sapiens (human)
carbohydrate transmembrane transport	Bile salt export pump	Homo sapiens (human)
bile acid signaling pathway	Bile salt export pump	Homo sapiens (human)
cholesterol homeostasis	Bile salt export pump	Homo sapiens (human)
response to estrogen	Bile salt export pump	Homo sapiens (human)
response to ethanol	Bile salt export pump	Homo sapiens (human)
xenobiotic export from cell	Bile salt export pump	Homo sapiens (human)
lipid homeostasis	Bile salt export pump	Homo sapiens (human)
phospholipid homeostasis	Bile salt export pump	Homo sapiens (human)
positive regulation of bile acid secretion	Bile salt export pump	Homo sapiens (human)
regulation of bile acid metabolic process	Bile salt export pump	Homo sapiens (human)
transmembrane transport	Bile salt export pump	Homo sapiens (human)
xenobiotic metabolic process	Solute carrier organic anion transporter family member 1A2	Homo sapiens (human)
monoatomic ion transport	Solute carrier organic anion transporter family member 1A2	Homo sapiens (human)
organic cation transport	Solute carrier organic anion transporter family member 1A2	Homo sapiens (human)
organic anion transport	Solute carrier organic anion transporter family member 1A2	Homo sapiens (human)
bile acid and bile salt transport	Solute carrier organic anion transporter family member 1A2	Homo sapiens (human)
sodium-independent organic anion transport	Solute carrier organic anion transporter family member 1A2	Homo sapiens (human)
transmembrane transport	Solute carrier organic anion transporter family member 1A2	Homo sapiens (human)
sodium ion transport	Ileal sodium/bile acid cotransporter	Homo sapiens (human)
response to bacterium	Ileal sodium/bile acid cotransporter	Homo sapiens (human)
bile acid and bile salt transport	Ileal sodium/bile acid cotransporter	Homo sapiens (human)
transmembrane transport	Ileal sodium/bile acid cotransporter	Homo sapiens (human)
sodium ion transport	Sodium/bile acid cotransporter	Homo sapiens (human)
response to organic cyclic compound	Sodium/bile acid cotransporter	Homo sapiens (human)
bile acid and bile salt transport	Sodium/bile acid cotransporter	Homo sapiens (human)
response to nutrient levels	Sodium/bile acid cotransporter	Homo sapiens (human)
bile acid signaling pathway	Sodium/bile acid cotransporter	Homo sapiens (human)
response to estrogen	Sodium/bile acid cotransporter	Homo sapiens (human)
response to ethanol	Sodium/bile acid cotransporter	Homo sapiens (human)
symbiont entry into host cell	Sodium/bile acid cotransporter	Homo sapiens (human)
transmembrane transport	Sodium/bile acid cotransporter	Homo sapiens (human)
cellular response to xenobiotic stimulus	Sodium/bile acid cotransporter	Homo sapiens (human)
regulation of bile acid secretion	Sodium/bile acid cotransporter	Homo sapiens (human)
cell surface bile acid receptor signaling pathway	G-protein coupled bile acid receptor 1	Homo sapiens (human)
positive regulation of ERK1 and ERK2 cascade	G-protein coupled bile acid receptor 1	Homo sapiens (human)
cellular response to bile acid	G-protein coupled bile acid receptor 1	Homo sapiens (human)
positive regulation of cholangiocyte proliferation	G-protein coupled bile acid receptor 1	Homo sapiens (human)
regulation of bicellular tight junction assembly	G-protein coupled bile acid receptor 1	Homo sapiens (human)
G protein-coupled receptor signaling pathway	G-protein coupled bile acid receptor 1	Homo sapiens (human)
monoatomic ion transport	Solute carrier organic anion transporter family member 4A1	Homo sapiens (human)
prostaglandin transport	Solute carrier organic anion transporter family member 4A1	Homo sapiens (human)
transmembrane transport	Solute carrier organic anion transporter family member 4A1	Homo sapiens (human)
thyroid hormone transport	Solute carrier organic anion transporter family member 4A1	Homo sapiens (human)
sodium-independent organic anion transport	Solute carrier organic anion transporter family member 4A1	Homo sapiens (human)
xenobiotic metabolic process	Solute carrier organic anion transporter family member 1B3	Homo sapiens (human)
monoatomic ion transport	Solute carrier organic anion transporter family member 1B3	Homo sapiens (human)
organic anion transport	Solute carrier organic anion transporter family member 1B3	Homo sapiens (human)
bile acid and bile salt transport	Solute carrier organic anion transporter family member 1B3	Homo sapiens (human)
heme catabolic process	Solute carrier organic anion transporter family member 1B3	Homo sapiens (human)
sodium-independent organic anion transport	Solute carrier organic anion transporter family member 1B3	Homo sapiens (human)
transmembrane transport	Solute carrier organic anion transporter family member 1B3	Homo sapiens (human)
xenobiotic metabolic process	Solute carrier organic anion transporter family member 1B1	Homo sapiens (human)
monoatomic ion transport	Solute carrier organic anion transporter family member 1B1	Homo sapiens (human)
organic anion transport	Solute carrier organic anion transporter family member 1B1	Homo sapiens (human)
bile acid and bile salt transport	Solute carrier organic anion transporter family member 1B1	Homo sapiens (human)
prostaglandin transport	Solute carrier organic anion transporter family member 1B1	Homo sapiens (human)
heme catabolic process	Solute carrier organic anion transporter family member 1B1	Homo sapiens (human)
sodium-independent organic anion transport	Solute carrier organic anion transporter family member 1B1	Homo sapiens (human)
transmembrane transport	Solute carrier organic anion transporter family member 1B1	Homo sapiens (human)
thyroid hormone transport	Solute carrier organic anion transporter family member 1B1	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
guanine nucleotide transmembrane transporter activity	Multidrug resistance-associated protein 4	Homo sapiens (human)
protein binding	Multidrug resistance-associated protein 4	Homo sapiens (human)
ATP binding	Multidrug resistance-associated protein 4	Homo sapiens (human)
ABC-type xenobiotic transporter activity	Multidrug resistance-associated protein 4	Homo sapiens (human)
prostaglandin transmembrane transporter activity	Multidrug resistance-associated protein 4	Homo sapiens (human)
urate transmembrane transporter activity	Multidrug resistance-associated protein 4	Homo sapiens (human)
purine nucleotide transmembrane transporter activity	Multidrug resistance-associated protein 4	Homo sapiens (human)
ABC-type glutathione S-conjugate transporter activity	Multidrug resistance-associated protein 4	Homo sapiens (human)
ABC-type bile acid transporter activity	Multidrug resistance-associated protein 4	Homo sapiens (human)
efflux transmembrane transporter activity	Multidrug resistance-associated protein 4	Homo sapiens (human)
15-hydroxyprostaglandin dehydrogenase (NAD+) activity	Multidrug resistance-associated protein 4	Homo sapiens (human)
ATP hydrolysis activity	Multidrug resistance-associated protein 4	Homo sapiens (human)
glutathione transmembrane transporter activity	Multidrug resistance-associated protein 4	Homo sapiens (human)
ATPase-coupled transmembrane transporter activity	Multidrug resistance-associated protein 4	Homo sapiens (human)
xenobiotic transmembrane transporter activity	Multidrug resistance-associated protein 4	Homo sapiens (human)
ATPase-coupled inorganic anion transmembrane transporter activity	Multidrug resistance-associated protein 4	Homo sapiens (human)
ABC-type transporter activity	Multidrug resistance-associated protein 4	Homo sapiens (human)
organic anion transmembrane transporter activity	Solute carrier organic anion transporter family member 2B1	Homo sapiens (human)
prostaglandin transmembrane transporter activity	Solute carrier organic anion transporter family member 2B1	Homo sapiens (human)
sodium-independent organic anion transmembrane transporter activity	Solute carrier organic anion transporter family member 2B1	Homo sapiens (human)
transmembrane transporter activity	Solute carrier organic anion transporter family member 2B1	Homo sapiens (human)
bile acid transmembrane transporter activity	Solute carrier organic anion transporter family member 2B1	Homo sapiens (human)
protein binding	Bile salt export pump	Homo sapiens (human)
ATP binding	Bile salt export pump	Homo sapiens (human)
ABC-type xenobiotic transporter activity	Bile salt export pump	Homo sapiens (human)
bile acid transmembrane transporter activity	Bile salt export pump	Homo sapiens (human)
canalicular bile acid transmembrane transporter activity	Bile salt export pump	Homo sapiens (human)
carbohydrate transmembrane transporter activity	Bile salt export pump	Homo sapiens (human)
ABC-type bile acid transporter activity	Bile salt export pump	Homo sapiens (human)
ATP hydrolysis activity	Bile salt export pump	Homo sapiens (human)
organic anion transmembrane transporter activity	Solute carrier organic anion transporter family member 1A2	Homo sapiens (human)
organic cation transmembrane transporter activity	Solute carrier organic anion transporter family member 1A2	Homo sapiens (human)
bile acid transmembrane transporter activity	Solute carrier organic anion transporter family member 1A2	Homo sapiens (human)
transmembrane transporter activity	Solute carrier organic anion transporter family member 1A2	Homo sapiens (human)
sodium-independent organic anion transmembrane transporter activity	Solute carrier organic anion transporter family member 1A2	Homo sapiens (human)
protein binding	Ileal sodium/bile acid cotransporter	Homo sapiens (human)
bile acid:sodium symporter activity	Ileal sodium/bile acid cotransporter	Homo sapiens (human)
virus receptor activity	Sodium/bile acid cotransporter	Homo sapiens (human)
protein binding	Sodium/bile acid cotransporter	Homo sapiens (human)
bile acid:sodium symporter activity	Sodium/bile acid cotransporter	Homo sapiens (human)
protein binding	G-protein coupled bile acid receptor 1	Homo sapiens (human)
bile acid receptor activity	G-protein coupled bile acid receptor 1	Homo sapiens (human)
G protein-coupled bile acid receptor activity	G-protein coupled bile acid receptor 1	Homo sapiens (human)
protein binding	Solute carrier organic anion transporter family member 4A1	Homo sapiens (human)
organic anion transmembrane transporter activity	Solute carrier organic anion transporter family member 4A1	Homo sapiens (human)
prostaglandin transmembrane transporter activity	Solute carrier organic anion transporter family member 4A1	Homo sapiens (human)
sodium-independent organic anion transmembrane transporter activity	Solute carrier organic anion transporter family member 4A1	Homo sapiens (human)
thyroid hormone transmembrane transporter activity	Solute carrier organic anion transporter family member 4A1	Homo sapiens (human)
serine-type endopeptidase inhibitor activity	Solute carrier organic anion transporter family member 1B3	Homo sapiens (human)
organic anion transmembrane transporter activity	Solute carrier organic anion transporter family member 1B3	Homo sapiens (human)
bile acid transmembrane transporter activity	Solute carrier organic anion transporter family member 1B3	Homo sapiens (human)
sodium-independent organic anion transmembrane transporter activity	Solute carrier organic anion transporter family member 1B3	Homo sapiens (human)
organic anion transmembrane transporter activity	Solute carrier organic anion transporter family member 1B1	Homo sapiens (human)
bile acid transmembrane transporter activity	Solute carrier organic anion transporter family member 1B1	Homo sapiens (human)
prostaglandin transmembrane transporter activity	Solute carrier organic anion transporter family member 1B1	Homo sapiens (human)
sodium-independent organic anion transmembrane transporter activity	Solute carrier organic anion transporter family member 1B1	Homo sapiens (human)
thyroid hormone transmembrane transporter activity	Solute carrier organic anion transporter family member 1B1	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
nucleolus	Multidrug resistance-associated protein 4	Homo sapiens (human)
Golgi apparatus	Multidrug resistance-associated protein 4	Homo sapiens (human)
plasma membrane	Multidrug resistance-associated protein 4	Homo sapiens (human)
membrane	Multidrug resistance-associated protein 4	Homo sapiens (human)
basolateral plasma membrane	Multidrug resistance-associated protein 4	Homo sapiens (human)
apical plasma membrane	Multidrug resistance-associated protein 4	Homo sapiens (human)
platelet dense granule membrane	Multidrug resistance-associated protein 4	Homo sapiens (human)
external side of apical plasma membrane	Multidrug resistance-associated protein 4	Homo sapiens (human)
plasma membrane	Multidrug resistance-associated protein 4	Homo sapiens (human)
plasma membrane	Solute carrier organic anion transporter family member 2B1	Homo sapiens (human)
basal plasma membrane	Solute carrier organic anion transporter family member 2B1	Homo sapiens (human)
apical plasma membrane	Solute carrier organic anion transporter family member 2B1	Homo sapiens (human)
basolateral plasma membrane	Solute carrier organic anion transporter family member 2B1	Homo sapiens (human)
apical plasma membrane	Solute carrier organic anion transporter family member 2B1	Homo sapiens (human)
basolateral plasma membrane	Bile salt export pump	Homo sapiens (human)
Golgi membrane	Bile salt export pump	Homo sapiens (human)
endosome	Bile salt export pump	Homo sapiens (human)
plasma membrane	Bile salt export pump	Homo sapiens (human)
cell surface	Bile salt export pump	Homo sapiens (human)
apical plasma membrane	Bile salt export pump	Homo sapiens (human)
intercellular canaliculus	Bile salt export pump	Homo sapiens (human)
intracellular canaliculus	Bile salt export pump	Homo sapiens (human)
recycling endosome	Bile salt export pump	Homo sapiens (human)
recycling endosome membrane	Bile salt export pump	Homo sapiens (human)
extracellular exosome	Bile salt export pump	Homo sapiens (human)
membrane	Bile salt export pump	Homo sapiens (human)
plasma membrane	Solute carrier organic anion transporter family member 1A2	Homo sapiens (human)
basal plasma membrane	Solute carrier organic anion transporter family member 1A2	Homo sapiens (human)
apical plasma membrane	Solute carrier organic anion transporter family member 1A2	Homo sapiens (human)
basolateral plasma membrane	Solute carrier organic anion transporter family member 1A2	Homo sapiens (human)
plasma membrane	Ileal sodium/bile acid cotransporter	Homo sapiens (human)
microvillus	Ileal sodium/bile acid cotransporter	Homo sapiens (human)
apical plasma membrane	Ileal sodium/bile acid cotransporter	Homo sapiens (human)
plasma membrane	Sodium/bile acid cotransporter	Homo sapiens (human)
basolateral plasma membrane	Sodium/bile acid cotransporter	Homo sapiens (human)
cytoplasm	G-protein coupled bile acid receptor 1	Homo sapiens (human)
plasma membrane	G-protein coupled bile acid receptor 1	Homo sapiens (human)
receptor complex	G-protein coupled bile acid receptor 1	Homo sapiens (human)
plasma membrane	G-protein coupled bile acid receptor 1	Homo sapiens (human)
plasma membrane	Solute carrier organic anion transporter family member 4A1	Homo sapiens (human)
basolateral plasma membrane	Solute carrier organic anion transporter family member 4A1	Homo sapiens (human)
plasma membrane	Solute carrier organic anion transporter family member 1B3	Homo sapiens (human)
basal plasma membrane	Solute carrier organic anion transporter family member 1B3	Homo sapiens (human)
basolateral plasma membrane	Solute carrier organic anion transporter family member 1B3	Homo sapiens (human)
plasma membrane	Solute carrier organic anion transporter family member 1B1	Homo sapiens (human)
basal plasma membrane	Solute carrier organic anion transporter family member 1B1	Homo sapiens (human)
membrane	Solute carrier organic anion transporter family member 1B1	Homo sapiens (human)
basolateral plasma membrane	Solute carrier organic anion transporter family member 1B1	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Assay ID	Title	Year	Journal	Article
AID682212	TP_TRANSPORTER: inhibition of E217betaG uptake (E217betaG: 0.055 uM, TC: 200 uM) in membrane vesicles from LLC-PK1 cells	2000	The Journal of biological chemistry, Jan-28, Volume: 275, Issue:4	ATP-dependent transport of bile salts by rat multidrug resistance-associated protein 3 (Mrp3).
AID680043	TP_TRANSPORTER: uptake of Taurocholate at 20 u M in Oatp1-expressing HeLa cells	2003	American journal of physiology. Gastrointestinal and liver physiology, Nov, Volume: 285, Issue:5	Substrate specificities of rat oatp1 and ntcp: implications for hepatic organic anion uptake.
AID678788	TP_TRANSPORTER: uptake in Xenopus laevis oocytes	1997	Proceedings of the National Academy of Sciences of the United States of America, Sep-16, Volume: 94, Issue:19	Isolation of a multispecific organic anion and cardiac glycoside transporter from rat brain.
AID588968	Substrates of transporters of clinical importance in the absorption and disposition of drugs, OATP2B1	2010	Nature reviews. Drug discovery, Mar, Volume: 9, Issue:3	Membrane transporters in drug development.
AID681651	TP_TRANSPORTER: uptake of Taurocholate at a concentration of 100 u M in membrane vesicles from Bsep-expressing Sf9 cells	2003	Journal of lipid research, Jan, Volume: 44, Issue:1	Physiological characteristics of allo-cholic acid.
AID680240	TP_TRANSPORTER: uptake in Xenopus laevis oocytes	1994	Proceedings of the National Academy of Sciences of the United States of America, Jan-04, Volume: 91, Issue:1	Expression cloning of a rat liver Na(+)-independent organic anion transporter.
AID679689	TP_TRANSPORTER: uptake (pH 5.0) of Taurocholate at a concentration of 59.6 u M in ASBT-expressing HEK293 cells	2004	The Journal of pharmacology and experimental therapeutics, Feb, Volume: 308, Issue:2	Functional characterization of pH-sensitive organic anion transporting polypeptide OATP-B in human.
AID681531	TP_TRANSPORTER: uptake of Cholate at a concentration of 1 u M in NTCP-expressing HeLa cells	2003	American journal of physiology. Gastrointestinal and liver physiology, Nov, Volume: 285, Issue:5	Substrate specificities of rat oatp1 and ntcp: implications for hepatic organic anion uptake.
AID681721	TP_TRANSPORTER: uptake in membrane vesicles isolated from Bsep-expressing Sf9 cells	1998	The Journal of biological chemistry, Apr-17, Volume: 273, Issue:16	The sister of P-glycoprotein represents the canalicular bile salt export pump of mammalian liver.
AID680584	TP_TRANSPORTER: inhibition of Etoposide glucuronide uptake (Etoposide glucuronide: 0.094 uM, TC: 500.0 uM) in membrane vesicles from MRP3-expressing Sf9 cells	2003	The Biochemical journal, Jan-01, Volume: 369, Issue:Pt 1	Transport of bile acids in multidrug-resistance-protein 3-overexpressing cells co-transfected with the ileal Na+-dependent bile-acid transporter.
AID681535	TP_TRANSPORTER: uptake in Ntcp-expressing COS-7 cells	1994	The American journal of physiology, Mar, Volume: 266, Issue:3 Pt 1	Expression and characterization of a functional rat liver Na+ bile acid cotransport system in COS-7 cells.
AID1209765	Drug accumulation in sandwich-cultured human adult hepatocytes assessed per mg protein under Ca2+/Mg2+ free conditions	2013	Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 41, Issue:2	Hepatobiliary disposition of 17-OHPC and taurocholate in fetal human hepatocytes: a comparison with adult human hepatocytes.
AID681537	TP_TRANSPORTER: transepithelial transport (basal to apical) in Ntcp-expressing MDCK cell	2005	American journal of physiology. Gastrointestinal and liver physiology, Jan, Volume: 288, Issue:1	Vectorial transport of bile salts across MDCK cells expressing both rat Na+-taurocholate cotransporting polypeptide and rat bile salt export pump.
AID679563	TP_TRANSPORTER: uptake in NTCP-expressing HeLa cells	1999	The Journal of pharmacology and experimental therapeutics, Dec, Volume: 291, Issue:3	Modulation by drugs of human hepatic sodium-dependent bile acid transporter (sodium taurocholate cotransporting polypeptide) activity.
AID679492	TP_TRANSPORTER: inhibition of E217betaG uptake in Oatp2-expressing LLC-PK1 cells	2001	The Journal of pharmacology and experimental therapeutics, Jul, Volume: 298, Issue:1	Characterization of the efflux transport of 17beta-estradiol-D-17beta-glucuronide from the brain across the blood-brain barrier.
AID680229	TP_TRANSPORTER: uptake of Cholate at 1 uM in Oatp1-expressing HeLa cells	2003	American journal of physiology. Gastrointestinal and liver physiology, Nov, Volume: 285, Issue:5	Substrate specificities of rat oatp1 and ntcp: implications for hepatic organic anion uptake.
AID679708	TP_TRANSPORTER: uptake in isolated mouse ileocytes	1999	Journal of biochemistry, Apr, Volume: 125, Issue:4	Characterization, cDNA cloning, and functional expression of mouse ileal sodium-dependent bile acid transporter.
AID679642	TP_TRANSPORTER: uptake in membrane vesicles isolated from Bsep-expressing Sf9 cells	2001	Hepatology (Baltimore, Md.), May, Volume: 33, Issue:5	Characterization of the mouse bile salt export pump overexpressed in the baculovirus system.
AID681342	TP_TRANSPORTER: uptake in Xenopus laevis oocytes	1999	The Journal of biological chemistry, Jun-11, Volume: 274, Issue:24	Identification of a novel gene family encoding human liver-specific organic anion transporter LST-1.
AID1552633	Substrate activity at human NTCP expressed in HEK293 cells harboring pEGFP assessed as V max for transporter-mediated drug uptake measured for 30 mins in presence of sodium chloride by UPLC-MS/MS analysis	2019	Bioorganic & medicinal chemistry, 08-15, Volume: 27, Issue:16	Synthesis, pharmacological evaluation, and mechanistic study of adefovir mixed phosphonate derivatives bearing cholic acid and l-amino acid moieties for the treatment of HBV.
AID679491	TP_TRANSPORTER: inhibition of Rocuronium uptake in Xenopus laevis oocytes	2001	The Journal of pharmacology and experimental therapeutics, Jul, Volume: 298, Issue:1	Comparison of "type I" and "type II" organic cation transport by organic cation transporters and organic anion-transporting polypeptides.
AID679452	TP_TRANSPORTER: inhibition of benzylpenicillin uptake by Taurocholate at a concentration of 1000uM in Oat3-expressing oocyte cells	2004	The Journal of pharmacology and experimental therapeutics, Jun, Volume: 309, Issue:3	Mouse reduced in osteosclerosis transporter functions as an organic anion transporter 3 and is localized at abluminal membrane of blood-brain barrier.
AID680593	TP_TRANSPORTER: inhibition of E217betaG uptake (E217betaG: 0.4 uM) in membrane vesicles from MRP3-expressing HEK cells	2003	Biochemistry, Aug-26, Volume: 42, Issue:33	Characterization of the role of polar amino acid residues within predicted transmembrane helix 17 in determining the substrate specificity of multidrug resistance protein 3.
AID681349	TP_TRANSPORTER: uptake in ASBT-expressing COS cells	2000	American journal of physiology. Gastrointestinal and liver physiology, Dec, Volume: 279, Issue:6	Expression, transport properties, and chromosomal location of organic anion transporter subtype 3.
AID680639	TP_TRANSPORTER: inhibition of BSP uptake (BSP: 2 uM, CA: 100 uM) in Xenopus laevis oocytes	1994	Hepatology (Baltimore, Md.), Aug, Volume: 20, Issue:2	Functional characterization of the basolateral rat liver organic anion transporting polypeptide.
AID681332	TP_TRANSPORTER: inhibition of Taurocholate uptake in ASBT-expressing COS cells	1998	The American journal of physiology, 01, Volume: 274, Issue:1	Expression and transport properties of the human ileal and renal sodium-dependent bile acid transporter.
AID679888	TP_TRANSPORTER: uptake in HepG2 cells	1996	Hepatology (Baltimore, Md.), May, Volume: 23, Issue:5	Molecular and functional characterization of bile acid transport in human hepatoblastoma HepG2 cells.
AID678922	TP_TRANSPORTER: Western (protein level: increase to 230 %) in vivo, liver of Him OF1 mouse	2001	Gastroenterology, Jul, Volume: 121, Issue:1	Effects of ursodeoxycholic and cholic acid feeding on hepatocellular transporter expression in mouse liver.
AID679476	TP_TRANSPORTER: uptake (pH 5.0) in OATP-B-expressing HEK293 cells	2004	The Journal of pharmacology and experimental therapeutics, Feb, Volume: 308, Issue:2	Functional characterization of pH-sensitive organic anion transporting polypeptide OATP-B in human.
AID678826	TP_TRANSPORTER: uptake in Oatp1-expressing COS-7 cells	1999	The Journal of pharmacology and experimental therapeutics, Feb, Volume: 288, Issue:2	Contribution of organic anion transporting polypeptide to uptake of its possible substrates into rat hepatocytes.
AID681578	TP_TRANSPORTER: uptake in OAT-K1-expressing MDCK cells	2001	The Journal of pharmacology and experimental therapeutics, Oct, Volume: 299, Issue:1	Multispecific substrate recognition of kidney-specific organic anion transporters OAT-K1 and OAT-K2.
AID681603	TP_TRANSPORTER: uptake in Xenopus laevis oocytes	1999	Molecular pharmacology, Apr, Volume: 55, Issue:4	Cloning and functional characterization of a new multispecific organic anion transporter, OAT-K2, in rat kidney.
AID534109	Ratio of MIC for Pasteurella multocida AL435 to MIC for TolC deficient Pasteurella multocida pm0527	2008	Antimicrobial agents and chemotherapy, Nov, Volume: 52, Issue:11	Characterization of TolC efflux pump proteins from Pasteurella multocida.
AID680460	TP_TRANSPORTER: inhibition of Gadoxetate uptake (Gadoxetate: 100 uM, TCA: 200 uM) in Xenopus laevis oocytes	1999	The Journal of pharmacology and experimental therapeutics, Jul, Volume: 290, Issue:1	Hepatic uptake of the magnetic resonance imaging contrast agent gadoxetate by the organic anion transporting polypeptide Oatp1.
AID681151	TP_TRANSPORTER: uptake in Xenopus laevis oocytes	2001	Gastroenterology, Feb, Volume: 120, Issue:2	Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver.
AID679226	TP_TRANSPORTER: inhibition of E217betaG uptake (E217betaG: 1 uM, TCA: 100 uM) in membrane vesicles from MRP7-expressing HEK293 cells	2003	Molecular pharmacology, Feb, Volume: 63, Issue:2	Characterization of the transport properties of human multidrug resistance protein 7 (MRP7, ABCC10).
AID681958	TP_TRANSPORTER: inhibition of MPP+ uptake (MPP+: 0.15 uM, TCA: 5000 uM) in Xenopus laevis oocytes	1997	Molecular pharmacology, Jun, Volume: 51, Issue:6	Cloning and functional expression of a human liver organic cation transporter.
AID681173	TP_TRANSPORTER: uptake in Xenopus laevis oocytes	2000	Biochemical and biophysical research communications, Sep-07, Volume: 275, Issue:3	Molecular identification of a rat novel organic anion transporter moat1, which transports prostaglandin D(2), leukotriene C(4), and taurocholate.
AID682153	TP_TRANSPORTER: Western in vivo, liver of C57BL/6J mouse	2002	Journal of hepatology, Nov, Volume: 37, Issue:5	Effects of bile salt flux variations on the expression of hepatic bile salt transporters in vivo in mice.
AID592681	Apparent permeability across human Caco2 cell membrane after 2 hrs by LC-MS/MS analysis	2011	Bioorganic & medicinal chemistry, Apr-15, Volume: 19, Issue:8	QSAR-based permeability model for drug-like compounds.
AID679480	TP_TRANSPORTER: uptake in Xenopus laevis oocytes	1998	The Journal of biological chemistry, Aug-28, Volume: 273, Issue:35	Molecular characterization and tissue distribution of a new organic anion transporter subtype (oatp3) that transports thyroid hormones and taurocholate and comparison with oatp2.
AID682216	TP_TRANSPORTER: inhibition of E217betaG uptake (E217betaG: 0.055 uM, CA: 500 uM) in membrane vesicles from LLC-PK1 cells	2000	The Journal of biological chemistry, Jan-28, Volume: 275, Issue:4	ATP-dependent transport of bile salts by rat multidrug resistance-associated protein 3 (Mrp3).
AID679139	TP_TRANSPORTER: uptake in membrane vesicles from LLC-PK1 cells	2000	The Journal of biological chemistry, Jan-28, Volume: 275, Issue:4	ATP-dependent transport of bile salts by rat multidrug resistance-associated protein 3 (Mrp3).
AID247743	Inhibition of [3H]taurocholate uptake in rat hepatocytes	2004	Bioorganic & medicinal chemistry letters, Aug-16, Volume: 14, Issue:16	Bile acid conjugates of a nonsteroidal glucocorticoid receptor modulator.
AID680420	TP_TRANSPORTER: inhibition of MTX uptake (MTX: 1 uM, TCA: 300 uM) in membrane vesicles from MRP3-expressing HEK293 cells	2001	Cancer research, Oct-01, Volume: 61, Issue:19	Transport of methotrexate (MTX) and folates by multidrug resistance protein (MRP) 3 and MRP1: effect of polyglutamylation on MTX transport.
AID681723	TP_TRANSPORTER: uptake in membrane vesicles from Bsep-expressing Sf9 cells	2003	Journal of lipid research, Jan, Volume: 44, Issue:1	Physiological characteristics of allo-cholic acid.
AID534111	Antibacterial activity against Pasteurella multocida pm1980 after 24 hrs by broth dilution method	2008	Antimicrobial agents and chemotherapy, Nov, Volume: 52, Issue:11	Characterization of TolC efflux pump proteins from Pasteurella multocida.
AID681360	TP_TRANSPORTER: uptake in Oatp3-expressing MDCK cells	2000	American journal of physiology. Gastrointestinal and liver physiology, Dec, Volume: 279, Issue:6	Expression, transport properties, and chromosomal location of organic anion transporter subtype 3.
AID1209767	Drug accumulation in sandwich-cultured human fetal hepatocytes assessed per mg protein under Ca2+/Mg2+ free conditions	2013	Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 41, Issue:2	Hepatobiliary disposition of 17-OHPC and taurocholate in fetal human hepatocytes: a comparison with adult human hepatocytes.
AID679490	TP_TRANSPORTER: uptake in Xenopus laevis oocytes	1998	The Journal of biological chemistry, Aug-28, Volume: 273, Issue:35	Molecular characterization and tissue distribution of a new organic anion transporter subtype (oatp3) that transports thyroid hormones and taurocholate and comparison with oatp2.
AID679687	TP_TRANSPORTER: uptake in ASBT-expressing HEK293 cells	2002	Biochemistry, Dec-17, Volume: 41, Issue:50	Identification of a region of the ileal-type sodium/bile acid cotransporter interacting with a competitive bile acid transport inhibitor.
AID681836	TP_TRANSPORTER: inhibition of Pravastatin uptake (Pravastatin: 30 uM, TCA: 300 uM) in Xenopus laevis oocytes	1999	Pharmaceutical research, Jun, Volume: 16, Issue:6	Pravastatin, an HMG-CoA reductase inhibitor, is transported by rat organic anion transporting polypeptide, oatp2.
AID681541	TP_TRANSPORTER: inhibition of Taurocholate uptake (Taurochorate: 17 uM, CA: 200 uM) in Xenopus laevis oocytes	1991	Proceedings of the National Academy of Sciences of the United States of America, Dec-01, Volume: 88, Issue:23	Functional expression cloning and characterization of the hepatocyte Na+/bile acid cotransport system.
AID679650	TP_TRANSPORTER: uptake in Xenopus laevis oocytes	2001	Endocrinology, May, Volume: 142, Issue:5	Identification of thyroid hormone transporters in humans: different molecules are involved in a tissue-specific manner.
AID680990	TP_TRANSPORTER: inhibition of E1S uptake by Taurocholate at a concentration of 30uM in membrane vesicle from BCRP-expressing K562 cells	2003	Molecular pharmacology, Sep, Volume: 64, Issue:3	Breast cancer resistance protein exports sulfated estrogens but not free estrogens.
AID404304	Effect on human MRP2-mediated estradiol-17-beta-glucuronide transport in Sf9 cells inverted membrane vesicles relative to control	2008	Journal of medicinal chemistry, Jun-12, Volume: 51, Issue:11	Prediction and identification of drug interactions with the human ATP-binding cassette transporter multidrug-resistance associated protein 2 (MRP2; ABCC2).
AID682135	TP_TRANSPORTER: uptake in Oatp1-expressing CHO-03 cell	1999	The American journal of physiology, 04, Volume: 276, Issue:4	Polyspecific substrate uptake by the hepatic organic anion transporter Oatp1 in stably transfected CHO cells.
AID1211312	Cellular uptake in HEK293 cells assessed as bovine OATP1A2-mediated drug uptake at 5 uM at pH 7.4 after 1 min	2013	Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 41, Issue:3	Identification of multiple binding sites for substrate transport in bovine organic anion transporting polypeptide 1a2.
AID682215	TP_TRANSPORTER: inhibition of E217betaG uptake (E217betaG: 0.055 uM, CA: 500 uM) in membrane vesicles isolated from Mrp3-expressing LLC-PK1 cells	2000	The Journal of biological chemistry, Jan-28, Volume: 275, Issue:4	ATP-dependent transport of bile salts by rat multidrug resistance-associated protein 3 (Mrp3).
AID681653	TP_TRANSPORTER: uptake in membrane vesicles from Bsep-expressing Sf9 cells	2003	Journal of lipid research, Jan, Volume: 44, Issue:1	Physiological characteristics of allo-cholic acid.
AID681722	TP_TRANSPORTER: uptake in membrane vesicles isolated from Bsep-expressing Sf9 cells	2001	Biochimica et biophysica acta, Mar-09, Volume: 1511, Issue:1	Characterization of bile acid transport mediated by multidrug resistance associated protein 2 and bile salt export pump.
AID515399	Cytotoxicity against human HuH7 cells assessed as cell viability at 500 uM after 24 hrs by MTT assay relative to control	2010	Bioorganic & medicinal chemistry, Sep-15, Volume: 18, Issue:18	Bile acid toxicity structure-activity relationships: correlations between cell viability and lipophilicity in a panel of new and known bile acids using an oesophageal cell line (HET-1A).
AID680583	TP_TRANSPORTER: inhibition of Etoposide glucuronide uptake (Etoposide glucuronide: 0.094 uM, TCA: 500 uM) by Taurocholate at a concentration of 500uM in membrane vesicle from MRP3-expressing Sf9 cells	2003	The Biochemical journal, Jan-01, Volume: 369, Issue:Pt 1	Transport of bile acids in multidrug-resistance-protein 3-overexpressing cells co-transfected with the ileal Na+-dependent bile-acid transporter.
AID1211311	Cellular uptake in HEK293 cells assessed as bovine OATP1A2-mediated drug uptake at 5 uM at pH 6 after 1 min	2013	Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 41, Issue:3	Identification of multiple binding sites for substrate transport in bovine organic anion transporting polypeptide 1a2.
AID1211306	Cellular uptake in HEK293 cells assessed as bovine high affinity site of OATP1A2-mediated drug uptake at 0.5 to 100 uM after 1 min by Eadie-Hofstee plot analysis	2013	Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 41, Issue:3	Identification of multiple binding sites for substrate transport in bovine organic anion transporting polypeptide 1a2.
AID679420	TP_TRANSPORTER: uptake (pH 7.4) of Taurocholate at a concentration of 0.15 u M in OATP-B-expressing HEK293 cells	2004	The Journal of pharmacology and experimental therapeutics, Feb, Volume: 308, Issue:2	Functional characterization of pH-sensitive organic anion transporting polypeptide OATP-B in human.
AID679789	TP_TRANSPORTER: inhibition of Daunomycin uptake in canalicular membrane vesicles from SD rat	1994	Hepatology (Baltimore, Md.), Jul, Volume: 20, Issue:1 Pt 1	Bile acid inhibition of P-glycoprotein-mediated transport in multidrug-resistant cells and rat liver canalicular membrane vesicles.
AID679477	TP_TRANSPORTER: uptake in Xenopus laevis oocytes	2002	The Journal of biological chemistry, Jul-26, Volume: 277, Issue:30	Impaired organic anion transport in kidney and choroid plexus of organic anion transporter 3 (Oat3 (Slc22a8)) knockout mice.
AID678809	TP_TRANSPORTER: uptake in Xenopus laevis oocytes	2001	Gastroenterology, Jun, Volume: 120, Issue:7	LST-2, a human liver-specific organic anion transporter, determines methotrexate sensitivity in gastrointestinal cancers.
AID24057	The compound was incubated with cholylglycine hydrolase and tested for determining the stability towards C-24 Deamination	1996	Journal of medicinal chemistry, May-24, Volume: 39, Issue:11	Synthesis and physicochemical, biological, and pharmacological properties of new bile acids amidated with cyclic amino acids.
AID679331	TP_TRANSPORTER: uptake in Oatp1-expressing Saccharomyces cerevisiae secretory vesicle	2003	American journal of physiology. Gastrointestinal and liver physiology, Aug, Volume: 285, Issue:2	N-glycosylation controls functional activity of Oatp1, an organic anion transporter.
AID680605	TP_TRANSPORTER: inhibition of Estradiol-17beta-D-glucuronide uptake by Taurocholate at a concentration of 10 uM in membrane vesicle from MRP8-expressing LLC-PK1 cells	2005	Molecular pharmacology, Feb, Volume: 67, Issue:2	Transport of bile acids, sulfated steroids, estradiol 17-beta-D-glucuronide, and leukotriene C4 by human multidrug resistance protein 8 (ABCC11).
AID679167	TP_TRANSPORTER: inhibition of DPDPE uptake (DPDPE: 0.02 uM) in Xenopus laevis oocytes	2003	The Journal of pharmacy and pharmacology, Jul, Volume: 55, Issue:7	Contribution of organic anion transporting polypeptide OATP-C to hepatic elimination of the opioid pentapeptide analogue [D-Ala2, D-Leu5]-enkephalin.
AID714190	Activity of OATP2B1 in rat jejunal epithelial cells	2012	Bioorganic & medicinal chemistry, Mar-01, Volume: 20, Issue:5	New fluorescent bile acids: synthesis, chemical characterization, and disastereoselective uptake by Caco-2 cells of 3-deoxy 3-NBD-amino deoxycholic and ursodeoxycholic acid.
AID680346	TP_TRANSPORTER: uptake in Oatp2-expressing LLC-PK1 cells	2002	Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 30, Issue:2	Effect of 17 beta-estradiol-D-17 beta-glucuronide on the rat organic anion transporting polypeptide 2-mediated transport differs depending on substrates.
AID681361	TP_TRANSPORTER: uptake in Oatp3-expressing COS cells	2000	American journal of physiology. Gastrointestinal and liver physiology, Dec, Volume: 279, Issue:6	Expression, transport properties, and chromosomal location of organic anion transporter subtype 3.
AID1896138	Antiviral activity against HBV infected human DMSO differentiated HuS-E/2 cells overexpressing NTCP assessed as assessed as inhibition of viral entry by measuring HBV mRNA level at 20 uM by qPCR analysis relative to control	2022	Journal of medicinal chemistry, 10-13, Volume: 65, Issue:19	Inhibiting Sodium Taurocholate Cotransporting Polypeptide in HBV-Related Diseases: From Biological Function to Therapeutic Potential.
AID699541	Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting	2012	Journal of medicinal chemistry, May-24, Volume: 55, Issue:10	Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions.
AID682020	TP_TRANSPORTER: inhibition of Taurocholate uptake (Taurocholate: 0.72 uM, CA: 72 uM) in Ntcp-expressing COS-7 cells	2002	Bioscience, biotechnology, and biochemistry, May, Volume: 66, Issue:5	Characterization of cloned mouse Na+/taurocholate cotransporting polypeptide by transient expression in COS-7 cells.
AID678976	TP_TRANSPORTER: uptake in membrane vesicle from MRP3-expressing Sf9 cells	2002	Pharmaceutical research, Jan, Volume: 19, Issue:1	Transport activity of human MRP3 expressed in Sf9 cells: comparative studies with rat MRP3.
AID681672	TP_TRANSPORTER: Western (protein level: reduction to 10% of control) in vivo, liver of Him OF1 mouse	2001	Gastroenterology, Jul, Volume: 121, Issue:1	Effects of ursodeoxycholic and cholic acid feeding on hepatocellular transporter expression in mouse liver.
AID1552631	Substrate activity at human NTCP expressed in HEK293 cells harboring pEGFP at 400 uM measured for 30 mins in presence of sodium chloride by UPLC-MS/MS analysis	2019	Bioorganic & medicinal chemistry, 08-15, Volume: 27, Issue:16	Synthesis, pharmacological evaluation, and mechanistic study of adefovir mixed phosphonate derivatives bearing cholic acid and l-amino acid moieties for the treatment of HBV.
AID422544	Reduction in human pancreatic recombinant 1B PLA2 activity expressed in Escherichia coli assessed as hydrolysis of 1,2-dimyristoyl-sn-3-glycerophosphocholine vesicles at 0.007 mol fraction relative to cholate	2009	Journal of natural products, Jan, Volume: 72, Issue:1	Effect of guggulsterone and cembranoids of Commiphora mukul on pancreatic phospholipase A(2): role in hypocholesterolemia.
AID681670	TP_TRANSPORTER: Western in vivo, liver of C57BL/6J mouse	2002	Journal of hepatology, Nov, Volume: 37, Issue:5	Effects of bile salt flux variations on the expression of hepatic bile salt transporters in vivo in mice.
AID1209766	Drug accumulation in sandwich-cultured human fetal hepatocytes assessed per mg protein under Ca2+/Mg2+ conditions	2013	Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 41, Issue:2	Hepatobiliary disposition of 17-OHPC and taurocholate in fetal human hepatocytes: a comparison with adult human hepatocytes.
AID678823	TP_TRANSPORTER: uptake in ASBT-expressing COS cells	1998	The American journal of physiology, 01, Volume: 274, Issue:1	Expression and transport properties of the human ileal and renal sodium-dependent bile acid transporter.
AID534110	Antibacterial activity against TolC deficient Pasteurella multocida pm1980 after 24 hrs by broth dilution method	2008	Antimicrobial agents and chemotherapy, Nov, Volume: 52, Issue:11	Characterization of TolC efflux pump proteins from Pasteurella multocida.
AID679713	TP_TRANSPORTER: inhibition of Taurocholate uptake (Taurocholate: 0.72 uM, CA: a 100-fold excess) in isolated mouse ileocytes	1999	Journal of biochemistry, Apr, Volume: 125, Issue:4	Characterization, cDNA cloning, and functional expression of mouse ileal sodium-dependent bile acid transporter.
AID681014	TP_TRANSPORTER: uptake in Xenopus laevis oocytes	2002	The Journal of biological chemistry, Jul-26, Volume: 277, Issue:30	Impaired organic anion transport in kidney and choroid plexus of organic anion transporter 3 (Oat3 (Slc22a8)) knockout mice.
AID681286	TP_TRANSPORTER: inhibition of DNP-SG uptake (DNP-SG: 0.01 uM, TCA: 10 uM) in membrane vesicles from GLC4/ADR cells	1997	Biochimica et biophysica acta, May-22, Volume: 1326, Issue:1	Anthracyclines modulate multidrug resistance protein (MRP) mediated organic anion transport.
AID283560	Antibacterial activity against Escherichia coli HNCE4 after 24 hrs	2007	Antimicrobial agents and chemotherapy, Mar, Volume: 51, Issue:3	Substrate competition studies using whole-cell accumulation assays with the major tripartite multidrug efflux pumps of Escherichia coli.
AID1211305	Cellular uptake in HEK293 cells assessed as human OATP1A2-mediated drug uptake at 0.05 uM after 1 min by Eadie-Hofstee plot analysis	2013	Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 41, Issue:3	Identification of multiple binding sites for substrate transport in bovine organic anion transporting polypeptide 1a2.
AID680617	TP_TRANSPORTER: inhibition of T3 uptake (T3: 1 uM, Taurochorate: 100 uM) in Xenopus laevis oocytes	2001	Endocrinology, May, Volume: 142, Issue:5	Identification of thyroid hormone transporters in humans: different molecules are involved in a tissue-specific manner.
AID681566	TP_TRANSPORTER: intracellular accumulation in Bsep-expressing LLC-PK1 cells	2000	Molecular pharmacology, Jan, Volume: 57, Issue:1	Cloning and expression of murine sister of P-glycoprotein reveals a more discriminating transporter than MDR1/P-glycoprotein.
AID681652	TP_TRANSPORTER: uptake in membrane vesicles isolated from Bsep-expressing Balb-3T3 cells	2000	Gene, Jan-04, Volume: 241, Issue:1	Molecular cloning and characterization of the murine bile salt export pump.
AID1552679	Substrate activity at human NTCP expressed in HEK293 cells harboring pEGFP assessed as V max/Km for transporter-mediated drug uptake measured for 30 mins in presence of sodium chloride by UPLC-MS/MS analysis	2019	Bioorganic & medicinal chemistry, 08-15, Volume: 27, Issue:16	Synthesis, pharmacological evaluation, and mechanistic study of adefovir mixed phosphonate derivatives bearing cholic acid and l-amino acid moieties for the treatment of HBV.
AID678825	TP_TRANSPORTER: inhibition of Rocuronium uptake in Xenopus laevis oocytes	2001	The Journal of pharmacology and experimental therapeutics, Jul, Volume: 298, Issue:1	Comparison of "type I" and "type II" organic cation transport by organic cation transporters and organic anion-transporting polypeptides.
AID681598	TP_TRANSPORTER: cell accumulation in OST-expressing oocytes	2003	The Journal of biological chemistry, Jul-25, Volume: 278, Issue:30	Functional complementation between a novel mammalian polygenic transport complex and an evolutionarily ancient organic solute transporter, OSTalpha-OSTbeta.
AID682022	TP_TRANSPORTER: Western (protein level: reduction to 30 % of control) in vivo, liver of Him OF1 mouse	2001	Gastroenterology, Jul, Volume: 121, Issue:1	Effects of ursodeoxycholic and cholic acid feeding on hepatocellular transporter expression in mouse liver.
AID1209741	Drug uptake in sandwich-cultured human fetal hepatocytes at 1 uM after 20 mins in presence of warm media at 37 degC by liquid scintillation counting method	2013	Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 41, Issue:2	Hepatobiliary disposition of 17-OHPC and taurocholate in fetal human hepatocytes: a comparison with adult human hepatocytes.
AID679338	TP_TRANSPORTER: uptake in Ntcp-expressing HPCT-1E3 cells	1996	European journal of cell biology, May, Volume: 70, Issue:1	Functional characterization of the hepatic sodium-dependent taurocholate transporter stably transfected into an immortalized liver-derived cell line and V79 fibroblasts.
AID510748	Antibacterial activity against Escherichia coli AG102MB harboring naive acrB gene	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Single nucleotide polymorphism analysis of the major tripartite multidrug efflux pump of Escherichia coli: functional conservation in disparate animal reservoirs despite exposure to antimicrobial chemotherapy.
AID682016	TP_TRANSPORTER: uptake in Ntcp-expressing COS-7 cells	2002	Bioscience, biotechnology, and biochemistry, May, Volume: 66, Issue:5	Characterization of cloned mouse Na+/taurocholate cotransporting polypeptide by transient expression in COS-7 cells.
AID681921	TP_TRANSPORTER: inhibition of E217betaG uptake in membrane vesicles from MRP4-expressing HEK-293 cells	2004	The international journal of biochemistry & cell biology, Feb, Volume: 36, Issue:2	Multidrug resistance protein 4 (MRP4/ABCC4) mediates efflux of bimane-glutathione.
AID534108	Antibacterial activity against Pasteurella multocida pm0527 after 24 hrs by broth dilution method	2008	Antimicrobial agents and chemotherapy, Nov, Volume: 52, Issue:11	Characterization of TolC efflux pump proteins from Pasteurella multocida.
AID681436	TP_TRANSPORTER: inhibition of E1S uptake (E1S: 40 uM, CA: 1000 uM) in Xenopus laevis oocytes	1999	The Journal of biological chemistry, May-07, Volume: 274, Issue:19	Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain.
AID681532	TP_TRANSPORTER: uptake in Xenopus laevis oocytes	1998	The American journal of physiology, 02, Volume: 274, Issue:2	Substrate specificity of the rat liver Na(+)-bile salt cotransporter in Xenopus laevis oocytes and in CHO cells.
AID681141	TP_TRANSPORTER: uptake in Xenopus laevis oocytes	2001	Molecular pharmacology, May, Volume: 59, Issue:5	Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.
AID681648	TP_TRANSPORTER: uptake in Xenopus laevis oocytes, splice variant (rlst-1)	1999	Gastroenterology, Oct, Volume: 117, Issue:4	Molecular characterization and functional regulation of a novel rat liver-specific organic anion transporter rlst-1.
AID324924	Agonist activity at human TGR5 expressed in CHO cells by luciferase assay relative to lithocholic acid	2008	Journal of medicinal chemistry, Mar-27, Volume: 51, Issue:6	Novel potent and selective bile acid derivatives as TGR5 agonists: biological screening, structure-activity relationships, and molecular modeling studies.
AID678808	TP_TRANSPORTER: uptake in Xenopus laevis oocytes	2000	FEBS letters, Jun-02, Volume: 474, Issue:2-3	Identification of organic anion transporting polypeptide 4 (Oatp4) as a major full-length isoform of the liver-specific transporter-1 (rlst-1) in rat liver.
AID681423	TP_TRANSPORTER: inhibition of E1S uptake (E1S: 40 uM, TCA: 1000 uM) in Xenopus laevis oocytes	1999	The Journal of biological chemistry, May-07, Volume: 274, Issue:19	Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain.
AID681571	TP_TRANSPORTER: RT-PCR in vivo, liver of CD-1 mouse	2002	The Journal of pharmacology and experimental therapeutics, Oct, Volume: 303, Issue:1	Inflammatory cytokines, but not bile acids, regulate expression of murine hepatic anion transporters in endotoxemia.
AID681593	TP_TRANSPORTER: uptake in OATP8-expressing HEK293 cells	2001	The Journal of biological chemistry, Mar-30, Volume: 276, Issue:13	Hepatic uptake of bilirubin and its conjugates by the human organic anion transporter SLC21A6.
AID324923	Agonist activity at human TGR5 expressed in CHO cells by luciferase assay	2008	Journal of medicinal chemistry, Mar-27, Volume: 51, Issue:6	Novel potent and selective bile acid derivatives as TGR5 agonists: biological screening, structure-activity relationships, and molecular modeling studies.
AID681346	TP_TRANSPORTER: ATP-dependent uptake in membrane vesicle from MRP8-expressing LLC-PK1 cells	2005	Molecular pharmacology, Feb, Volume: 67, Issue:2	Transport of bile acids, sulfated steroids, estradiol 17-beta-D-glucuronide, and leukotriene C4 by human multidrug resistance protein 8 (ABCC11).
AID515398	Cytotoxicity against human HET-1A cells assessed as cell viability after 24 hrs by MTT assay	2010	Bioorganic & medicinal chemistry, Sep-15, Volume: 18, Issue:18	Bile acid toxicity structure-activity relationships: correlations between cell viability and lipophilicity in a panel of new and known bile acids using an oesophageal cell line (HET-1A).
AID679961	TP_TRANSPORTER: uptake in Oatp1-expressing HeLa cells	1996	The American journal of physiology, Feb, Volume: 270, Issue:2 Pt 2	Estradiol 17 beta-D-glucuronide is a high-affinity substrate for oatp organic anion transporter.
AID679944	TP_TRANSPORTER: uptake in OAT-K2-expressing MDCK cells	1999	Molecular pharmacology, Apr, Volume: 55, Issue:4	Cloning and functional characterization of a new multispecific organic anion transporter, OAT-K2, in rat kidney.
AID679935	TP_TRANSPORTER: inhibition of Rhodamine 123 efflux (R123: 5 ug/mL, TCA: 200 uM) in P1(0.5) cells	1994	Hepatology (Baltimore, Md.), Jul, Volume: 20, Issue:1 Pt 1	Bile acid inhibition of P-glycoprotein-mediated transport in multidrug-resistant cells and rat liver canalicular membrane vesicles.
AID681900	TP_TRANSPORTER: inhibition of Taurocholate uptake in the presence of Cholate at a concentration of 20uM in membrane vesicles from MRP4-expressing V79 cells	2003	Hepatology (Baltimore, Md.), Aug, Volume: 38, Issue:2	Cotransport of reduced glutathione with bile salts by MRP4 (ABCC4) localized to the basolateral hepatocyte membrane.
AID679290	TP_TRANSPORTER: inhibition of E217betaG uptake in Oat3-expressing LLC-PK1 cells	2001	The Journal of pharmacology and experimental therapeutics, Jul, Volume: 298, Issue:1	Characterization of the efflux transport of 17beta-estradiol-D-17beta-glucuronide from the brain across the blood-brain barrier.
AID681597	TP_TRANSPORTER: cell accumulation in OST-expressing oocytes	2003	The Journal of biological chemistry, Jul-25, Volume: 278, Issue:30	Functional complementation between a novel mammalian polygenic transport complex and an evolutionarily ancient organic solute transporter, OSTalpha-OSTbeta.
AID680343	TP_TRANSPORTER: inhibition of PAH uptake in Oat1-expressing LLC-PK1 cells	2001	The Journal of pharmacology and experimental therapeutics, Jul, Volume: 298, Issue:1	Characterization of the efflux transport of 17beta-estradiol-D-17beta-glucuronide from the brain across the blood-brain barrier.
AID682049	TP_TRANSPORTER: intracellular accumulation/efflux in MDR1-expressing MDCKII cells	2000	Molecular pharmacology, Jan, Volume: 57, Issue:1	Cloning and expression of murine sister of P-glycoprotein reveals a more discriminating transporter than MDR1/P-glycoprotein.
AID681352	TP_TRANSPORTER: transepithelial transport (basal to apical) in Ntcp/Bsep double transfected MDCK cell	2005	American journal of physiology. Gastrointestinal and liver physiology, Jan, Volume: 288, Issue:1	Vectorial transport of bile salts across MDCK cells expressing both rat Na+-taurocholate cotransporting polypeptide and rat bile salt export pump.
AID1211300	Cellular uptake in HEK293 cells assessed as bovine OATP1A2-mediated drug uptake at 5 uM by liquid scintillation counting	2013	Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 41, Issue:3	Identification of multiple binding sites for substrate transport in bovine organic anion transporting polypeptide 1a2.
AID680937	TP_TRANSPORTER: uptake in membrane vesicles prepared from High Five cells infected with the ABCB11 baculovirus	2002	Gastroenterology, Nov, Volume: 123, Issue:5	The human bile salt export pump: characterization of substrate specificity and identification of inhibitors.
AID681365	TP_TRANSPORTER: uptake in OATP-C-expressing HEK293 cells	2001	The Journal of biological chemistry, Mar-30, Volume: 276, Issue:13	Hepatic uptake of bilirubin and its conjugates by the human organic anion transporter SLC21A6.
AID681135	TP_TRANSPORTER: uptake in OATP-F-expressing CHO cells	2002	Molecular endocrinology (Baltimore, Md.), Oct, Volume: 16, Issue:10	Identification of a novel human organic anion transporting polypeptide as a high affinity thyroxine transporter.
AID1211302	Cellular uptake in HEK293 cells assessed as bovine OATP1A2-mediated drug uptake at 5 uM up to 5 mins by liquid scintillation counting	2013	Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 41, Issue:3	Identification of multiple binding sites for substrate transport in bovine organic anion transporting polypeptide 1a2.
AID679681	TP_TRANSPORTER: inhibition of Taurocholate uptake (Taurochorate: 10 uM, CA: 100 uM) in Xenopus laevis oocytes	1994	The Journal of clinical investigation, Mar, Volume: 93, Issue:3	Molecular cloning, chromosomal localization, and functional characterization of a human liver Na+/bile acid cotransporter.
AID679138	TP_TRANSPORTER: uptake in membrane vesicles isolated from Mrp3-expressing LLC-PK1 cells	2000	The Journal of biological chemistry, Jan-28, Volume: 275, Issue:4	ATP-dependent transport of bile salts by rat multidrug resistance-associated protein 3 (Mrp3).
AID682083	TP_TRANSPORTER: inhibition of BSP uptake (BSP: 10 uM, CA: 100 uM) in Xenopus laevis oocytes	1995	Gastroenterology, Oct, Volume: 109, Issue:4	Molecular and functional characterization of an organic anion transporting polypeptide cloned from human liver.
AID681725	TP_TRANSPORTER: uptake in liver canalicular membrane vesicle from male rat	2001	Toxicology, Oct-05, Volume: 167, Issue:1	Troglitazone-induced intrahepatic cholestasis by an interference with the hepatobiliary export of bile acids in male and female rats. Correlation with the gender difference in troglitazone sulfate formation and the inhibition of the canalicular bile salt
AID681011	TP_TRANSPORTER: Western (protein level: increase to 220%) in vivo, liver of Him OF1 mouse	2001	Gastroenterology, Jul, Volume: 121, Issue:1	Effects of ursodeoxycholic and cholic acid feeding on hepatocellular transporter expression in mouse liver.
AID681845	TP_TRANSPORTER: inhibition of Digoxin uptake in Oatp2-expressing LLC-PK1 cells	2002	Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 30, Issue:2	Effect of 17 beta-estradiol-D-17 beta-glucuronide on the rat organic anion transporting polypeptide 2-mediated transport differs depending on substrates.
AID681525	TP_TRANSPORTER: uptake of Taurocholate at a concentration of 20 u M in Ntcp-expressing CHO cells	2003	Journal of lipid research, Jan, Volume: 44, Issue:1	Physiological characteristics of allo-cholic acid.
AID681661	TP_TRANSPORTER: inhibition of Taurocholate uptake (Taurochorate: 5 uM, CA: 50 uM) in membrane vesicles isolated from Bsep-expressing Balb-3T3 cells	2000	Gene, Jan-04, Volume: 241, Issue:1	Molecular cloning and characterization of the murine bile salt export pump.
AID681724	TP_TRANSPORTER: uptake in membrane vesicles from Bsep-expressing Sf9 cells	2000	Molecular pharmacology, Mar, Volume: 57, Issue:3	Transport function and hepatocellular localization of mrp6 in rat liver.
AID681378	TP_TRANSPORTER: inhibition of Taurocholate uptake in NTCP-expressing HeLa cells	1999	The Journal of pharmacology and experimental therapeutics, Dec, Volume: 291, Issue:3	Modulation by drugs of human hepatic sodium-dependent bile acid transporter (sodium taurocholate cotransporting polypeptide) activity.
AID248823	Inhibition of glucocorticoid receptor Dexamethasone response in reporter gene assay; Not determined	2004	Bioorganic & medicinal chemistry letters, Aug-16, Volume: 14, Issue:16	Bile acid conjugates of a nonsteroidal glucocorticoid receptor modulator.
AID682196	TP_TRANSPORTER: inhibition of F-MTX uptake (F-MTX: 5.0 uM, TC: 200.0 uM) in membrane vesicles from IEC-6 cells	2003	American journal of physiology. Gastrointestinal and liver physiology, Sep, Volume: 285, Issue:3	Transport of fluorescein methotrexate by multidrug resistance-associated protein 3 in IEC-6 cells.
AID422546	Apparent inhibition of human pancreatic recombinant 1B PLA2 activity expressed in Escherichia coli assessed as hydrolysis rate of 1,2-dimyristoyl-sn-3-glycerophosphocholine vesicles	2009	Journal of natural products, Jan, Volume: 72, Issue:1	Effect of guggulsterone and cembranoids of Commiphora mukul on pancreatic phospholipase A(2): role in hypocholesterolemia.
AID681604	TP_TRANSPORTER: inhibition of MTX uptake in OAT-K1-expressing MDCK cells	2000	The Journal of pharmacology and experimental therapeutics, Jun, Volume: 293, Issue:3	Trans-stimulation effects of folic acid derivatives on methotrexate transport by rat renal organic anion transporter, OAT-K1.
AID682142	TP_TRANSPORTER: RT-PCR in vivo, liver of CD-1 mouse	2002	The Journal of pharmacology and experimental therapeutics, Oct, Volume: 303, Issue:1	Inflammatory cytokines, but not bile acids, regulate expression of murine hepatic anion transporters in endotoxemia.
AID681367	TP_TRANSPORTER: uptake in Xenopus laevis oocytes	2003	American journal of physiology. Renal physiology, Dec, Volume: 285, Issue:6	Molecular characterization of human and rat organic anion transporter OATP-D.
AID681369	TP_TRANSPORTER: inhibition of L-T4 uptake in Oatp14-expressing HEK293 cells	2004	Endocrinology, Sep, Volume: 145, Issue:9	Involvement of multispecific organic anion transporter, Oatp14 (Slc21a14), in the transport of thyroxine across the blood-brain barrier.
AID679967	TP_TRANSPORTER: uptake in Oatp1-expressing 293c18 cells	1999	The Journal of biological chemistry, Dec-24, Volume: 274, Issue:52	A novel human hepatic organic anion transporting polypeptide (OATP2). Identification of a liver-specific human organic anion transporting polypeptide and identification of rat and human hydroxymethylglutaryl-CoA reductase inhibitor transporters.
AID681568	TP_TRANSPORTER: RT-PCR in vivo, liver of CD-1 mouse	2002	The Journal of pharmacology and experimental therapeutics, Oct, Volume: 303, Issue:1	Inflammatory cytokines, but not bile acids, regulate expression of murine hepatic anion transporters in endotoxemia.
AID680265	TP_TRANSPORTER: inhibition of Pravastatin uptake (Pravastatin: 0.5 uM, Taurocholate: 50 uM) in Oatp1-expressing 293c18 cells	1999	The Journal of biological chemistry, Dec-24, Volume: 274, Issue:52	A novel human hepatic organic anion transporting polypeptide (OATP2). Identification of a liver-specific human organic anion transporting polypeptide and identification of rat and human hydroxymethylglutaryl-CoA reductase inhibitor transporters.
AID679970	TP_TRANSPORTER: inhibition of E217betaG uptake in Oatp1-expressing LLC-PK1 cells	2001	The Journal of pharmacology and experimental therapeutics, Jul, Volume: 298, Issue:1	Characterization of the efflux transport of 17beta-estradiol-D-17beta-glucuronide from the brain across the blood-brain barrier.
AID534106	Antibacterial activity against Pasteurella multocida AL435 after 24 hrs by broth dilution method	2008	Antimicrobial agents and chemotherapy, Nov, Volume: 52, Issue:11	Characterization of TolC efflux pump proteins from Pasteurella multocida.
AID283561	Effect on modulation in uptake of [3H]progesterone in Escherichia coli AG102 with marR1 mutation	2007	Antimicrobial agents and chemotherapy, Mar, Volume: 51, Issue:3	Substrate competition studies using whole-cell accumulation assays with the major tripartite multidrug efflux pumps of Escherichia coli.
AID680640	TP_TRANSPORTER: inhibition of BSP uptake (BSP: 1 uM, TCA: 100 uM) in Oatp1-expressing HeLa cells	1996	The American journal of physiology, Feb, Volume: 270, Issue:2 Pt 2	Transient expression of oatp organic anion transporter in mammalian cells: identification of candidate substrates.
AID682155	TP_TRANSPORTER: uptake in liver canalicular membrane vesicle from female rat	2001	Toxicology, Oct-05, Volume: 167, Issue:1	Troglitazone-induced intrahepatic cholestasis by an interference with the hepatobiliary export of bile acids in male and female rats. Correlation with the gender difference in troglitazone sulfate formation and the inhibition of the canalicular bile salt
AID24058	The compound was incubated with human stools and tested for determining the stability towards 7 dehydroxylation	1996	Journal of medicinal chemistry, May-24, Volume: 39, Issue:11	Synthesis and physicochemical, biological, and pharmacological properties of new bile acids amidated with cyclic amino acids.
AID682158	TP_TRANSPORTER: inhibition of Pravastatin uptake (Pravastatin: 30 uM, CA: 300 uM) in Xenopus laevis oocytes	1999	Pharmaceutical research, Jun, Volume: 16, Issue:6	Pravastatin, an HMG-CoA reductase inhibitor, is transported by rat organic anion transporting polypeptide, oatp2.
AID681602	TP_TRANSPORTER: uptake in Xenopus laevis oocytes	1997	Hepatology (Baltimore, Md.), Dec, Volume: 26, Issue:6	Substrate specificity of sinusoidal bile acid and organic anion uptake systems in rat and human liver.
AID678924	TP_TRANSPORTER: RT-PCR (mRNA level: a 4-fold increase) in vivo, liver of Him OF1 mouse	2001	Gastroenterology, Jul, Volume: 121, Issue:1	Effects of ursodeoxycholic and cholic acid feeding on hepatocellular transporter expression in mouse liver.
AID510747	Antibacterial activity against Escherichia coli AG102MB harboring pSport1-based acrB gene	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Single nucleotide polymorphism analysis of the major tripartite multidrug efflux pump of Escherichia coli: functional conservation in disparate animal reservoirs despite exposure to antimicrobial chemotherapy.
AID682037	TP_TRANSPORTER: uptake in Xenopus laevis oocytes	1995	Gastroenterology, Oct, Volume: 109, Issue:4	Molecular and functional characterization of an organic anion transporting polypeptide cloned from human liver.
AID1552632	Substrate activity at human NTCP expressed in HEK293 cells harboring pEGFP assessed as Km for transporter-mediated drug uptake measured for 30 mins in presence of sodium chloride by UPLC-MS/MS analysis	2019	Bioorganic & medicinal chemistry, 08-15, Volume: 27, Issue:16	Synthesis, pharmacological evaluation, and mechanistic study of adefovir mixed phosphonate derivatives bearing cholic acid and l-amino acid moieties for the treatment of HBV.
AID680005	TP_TRANSPORTER: inhibition of Taurocholate uptake (Taurochorate: 10 uM, CA: 200 uM) in Xenopus laevis oocytes	1995	Gastroenterology, Oct, Volume: 109, Issue:4	Molecular and functional characterization of an organic anion transporting polypeptide cloned from human liver.
AID678978	TP_TRANSPORTER: uptake in Xenopus laevis oocytes	2001	Endocrinology, May, Volume: 142, Issue:5	Identification of thyroid hormone transporters in humans: different molecules are involved in a tissue-specific manner.
AID679118	TP_TRANSPORTER: uptake in NTCP-expressing HeLa cells	2003	American journal of physiology. Gastrointestinal and liver physiology, Nov, Volume: 285, Issue:5	Substrate specificities of rat oatp1 and ntcp: implications for hepatic organic anion uptake.
AID1209764	Drug accumulation in sandwich-cultured human adult hepatocytes assessed per mg protein under Ca2+/Mg2+ conditions	2013	Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 41, Issue:2	Hepatobiliary disposition of 17-OHPC and taurocholate in fetal human hepatocytes: a comparison with adult human hepatocytes.
AID510749	Antibacterial activity against Escherichia coli AG102MB harboring pP10-based acrB gene	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Single nucleotide polymorphism analysis of the major tripartite multidrug efflux pump of Escherichia coli: functional conservation in disparate animal reservoirs despite exposure to antimicrobial chemotherapy.
AID681592	TP_TRANSPORTER: uptake in Xenopus laevis oocytes	2000	The Biochemical journal, Jan-01, Volume: 345 Pt 1	Molecular cloning and functional characterization of the mouse organic-anion-transporting polypeptide 1 (Oatp1) and mapping of the gene to chromosome X.
AID283559	Antibacterial activity against Escherichia coli AG102MB after 24 hrs	2007	Antimicrobial agents and chemotherapy, Mar, Volume: 51, Issue:3	Substrate competition studies using whole-cell accumulation assays with the major tripartite multidrug efflux pumps of Escherichia coli.
AID680936	TP_TRANSPORTER: RT-PCR (mRNA level: a 8-fold increase) in vivo, liver of Him OF1 mouse	2001	Gastroenterology, Jul, Volume: 121, Issue:1	Effects of ursodeoxycholic and cholic acid feeding on hepatocellular transporter expression in mouse liver.
AID680045	TP_TRANSPORTER: uptake of Taurocholate at 1 u M in Oatp1-expressing HeLa cells	2003	American journal of physiology. Gastrointestinal and liver physiology, Nov, Volume: 285, Issue:5	Substrate specificities of rat oatp1 and ntcp: implications for hepatic organic anion uptake.
AID515400	Cytotoxicity against human HET-1A cells assessed as cell viability at 500 uM after 24 hrs by MTT assay relative to control	2010	Bioorganic & medicinal chemistry, Sep-15, Volume: 18, Issue:18	Bile acid toxicity structure-activity relationships: correlations between cell viability and lipophilicity in a panel of new and known bile acids using an oesophageal cell line (HET-1A).
AID680631	TP_TRANSPORTER: inhibition of BSP uptake (BSP: 2 uM, TCA: 100 uM) in Xenopus laevis oocytes	1994	Hepatology (Baltimore, Md.), Aug, Volume: 20, Issue:2	Functional characterization of the basolateral rat liver organic anion transporting polypeptide.
AID510750	Antibacterial activity against Escherichia coli AG102MB harboring pS1328-based acrB gene	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Single nucleotide polymorphism analysis of the major tripartite multidrug efflux pump of Escherichia coli: functional conservation in disparate animal reservoirs despite exposure to antimicrobial chemotherapy.
AID678960	TP_TRANSPORTER: uptake in OATP-C-expressing 293c18 cells	1999	The Journal of biological chemistry, Dec-24, Volume: 274, Issue:52	A novel human hepatic organic anion transporting polypeptide (OATP2). Identification of a liver-specific human organic anion transporting polypeptide and identification of rat and human hydroxymethylglutaryl-CoA reductase inhibitor transporters.
AID534107	Antibacterial activity against TolC deficient Pasteurella multocida pm0527 after 24 hrs by broth dilution method	2008	Antimicrobial agents and chemotherapy, Nov, Volume: 52, Issue:11	Characterization of TolC efflux pump proteins from Pasteurella multocida.
AID699540	Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting	2012	Journal of medicinal chemistry, May-24, Volume: 55, Issue:10	Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions.
AID283558	Antibacterial activity against Escherichia coli AG102 with marR1 mutation after 24 hrs	2007	Antimicrobial agents and chemotherapy, Mar, Volume: 51, Issue:3	Substrate competition studies using whole-cell accumulation assays with the major tripartite multidrug efflux pumps of Escherichia coli.
AID681045	TP_TRANSPORTER: inhibition of E1S uptake (E1S: 0.05 uM, TCA: 5 uM) in Xenopus laevis oocytes	2001	Molecular pharmacology, May, Volume: 59, Issue:5	Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.
AID680644	TP_TRANSPORTER: inhibition of BSP uptake (BSP: 1 uM, CA: 100 uM) in Oatp1-expressing HeLa cells	1996	The American journal of physiology, Feb, Volume: 270, Issue:2 Pt 2	Transient expression of oatp organic anion transporter in mammalian cells: identification of candidate substrates.
AID679561	TP_TRANSPORTER: uptake in Xenopus laevis oocytes	1994	The Journal of clinical investigation, Mar, Volume: 93, Issue:3	Molecular cloning, chromosomal localization, and functional characterization of a human liver Na+/bile acid cotransporter.
AID534112	Ratio of MIC for Pasteurella multocida AL435 to MIC for TolC deficient Pasteurella multocida pm1980	2008	Antimicrobial agents and chemotherapy, Nov, Volume: 52, Issue:11	Characterization of TolC efflux pump proteins from Pasteurella multocida.
AID1209740	Drug uptake in sandwich-cultured human fetal hepatocytes at 1 uM after 20 mins in presence of cold media at 4 degC by liquid scintillation counting method	2013	Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 41, Issue:2	Hepatobiliary disposition of 17-OHPC and taurocholate in fetal human hepatocytes: a comparison with adult human hepatocytes.
AID680034	TP_TRANSPORTER: inhibition of BSP uptake (BSP: 10 uM, TCA: 100 uM) in Xenopus laevis oocytes	1995	Gastroenterology, Oct, Volume: 109, Issue:4	Molecular and functional characterization of an organic anion transporting polypeptide cloned from human liver.
AID679790	TP_TRANSPORTER: inhibition of Daunomycin uptake in canalicular membrane vesicles	1994	Hepatology (Baltimore, Md.), Jul, Volume: 20, Issue:1 Pt 1	Bile acid inhibition of P-glycoprotein-mediated transport in multidrug-resistant cells and rat liver canalicular membrane vesicles.
AID679688	TP_TRANSPORTER: uptake (pH 7.4) of Taurocholate at a concentration of 60.2 u M in ASBT-expressing HEK293 cells	2004	The Journal of pharmacology and experimental therapeutics, Feb, Volume: 308, Issue:2	Functional characterization of pH-sensitive organic anion transporting polypeptide OATP-B in human.
AID679966	TP_TRANSPORTER: uptake in Oatp1-expressing CHO cells	2003	Journal of lipid research, Jan, Volume: 44, Issue:1	Physiological characteristics of allo-cholic acid.
AID682211	TP_TRANSPORTER: inhibition of E217betaG uptake (E217betaG: 0.055 uM, TCA: 200 uM) in membrane vesicles isolated from Mrp3-expressing LLC-PK1 cells	2000	The Journal of biological chemistry, Jan-28, Volume: 275, Issue:4	ATP-dependent transport of bile salts by rat multidrug resistance-associated protein 3 (Mrp3).
AID681217	TP_TRANSPORTER: inhibition of PGE2 uptake (PGE2: 0.015 uM) by Taurocholate at 0.15uM in Xenopus laevis oocytes	2003	American journal of physiology. Renal physiology, Dec, Volume: 285, Issue:6	Molecular characterization of human and rat organic anion transporter OATP-D.
AID699539	Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting	2012	Journal of medicinal chemistry, May-24, Volume: 55, Issue:10	Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions.
AID680244	TP_TRANSPORTER: uptake in Oatp1-expressing HeLa cells	1997	The Journal of biological chemistry, Oct-17, Volume: 272, Issue:42	Organic anion transporting polypeptide mediates organic anion/HCO3- exchange.
AID681362	TP_TRANSPORTER: uptake in Xenopus laevis oocytes	1997	The Journal of biological chemistry, Jul-25, Volume: 272, Issue:30	Expression cloning and characterization of a novel multispecific organic anion transporter.
AID679217	TP_TRANSPORTER: efflux in truncated ASBT-expressing Xenopus laevis oocytes	2000	Proceedings of the National Academy of Sciences of the United States of America, Sep-26, Volume: 97, Issue:20	Alternative splicing of the rat sodium/bile acid transporter changes its cellular localization and transport properties.
AID681567	TP_TRANSPORTER: RT-PCR in vivo, liver of CD-1 mouse	2002	The Journal of pharmacology and experimental therapeutics, Oct, Volume: 303, Issue:1	Inflammatory cytokines, but not bile acids, regulate expression of murine hepatic anion transporters in endotoxemia.
AID681833	TP_TRANSPORTER: inhibition of Taurocholate uptake (Taurochorate: 1 uM, CA: 200 uM, data not shown) in Xenopus laevis oocytes	1998	The Journal of biological chemistry, Aug-28, Volume: 273, Issue:35	Molecular characterization and tissue distribution of a new organic anion transporter subtype (oatp3) that transports thyroid hormones and taurocholate and comparison with oatp2.
AID680573	TP_TRANSPORTER: inhibition of Pravastatin uptake (Pravastatin: 0.5 uM, Taurocholate: 50 uM) in OATP-C-expressing 293c18 cells	1999	The Journal of biological chemistry, Dec-24, Volume: 274, Issue:52	A novel human hepatic organic anion transporting polypeptide (OATP2). Identification of a liver-specific human organic anion transporting polypeptide and identification of rat and human hydroxymethylglutaryl-CoA reductase inhibitor transporters.
AID679709	TP_TRANSPORTER: uptake in ASBT-expressing HEK293 cells	2002	Biochemistry, Dec-17, Volume: 41, Issue:50	Identification of a region of the ileal-type sodium/bile acid cotransporter interacting with a competitive bile acid transport inhibitor.
AID679153	TP_TRANSPORTER: RT-PCR in vivo, liver of CD-1 mouse	2002	The Journal of pharmacology and experimental therapeutics, Oct, Volume: 303, Issue:1	Inflammatory cytokines, but not bile acids, regulate expression of murine hepatic anion transporters in endotoxemia.
AID681012	TP_TRANSPORTER: RT-PCR (mRNA level: a 3-fold increase) in vivo, liver of Him OF1 mouse	2001	Gastroenterology, Jul, Volume: 121, Issue:1	Effects of ursodeoxycholic and cholic acid feeding on hepatocellular transporter expression in mouse liver.
AID679365	TP_TRANSPORTER: inhibition of Salicylate uptake (salicylate: 1 uM, CA: 1000 uM) in Xenopus laevis oocytes	1998	FEBS letters, Jun-12, Volume: 429, Issue:2	Identification of multispecific organic anion transporter 2 expressed predominantly in the liver.
AID422543	Reduction in human pancreatic recombinant 1B PLA2 activity expressed in Escherichia coli assessed as hydrolysis of 1,2-dimyristoyl-sn-3-glycerophosphocholine vesicles at 0.03 mol fraction relative to cholate	2009	Journal of natural products, Jan, Volume: 72, Issue:1	Effect of guggulsterone and cembranoids of Commiphora mukul on pancreatic phospholipase A(2): role in hypocholesterolemia.
AID680238	TP_TRANSPORTER: uptake in Xenopus laevis oocytes	1994	Hepatology (Baltimore, Md.), Aug, Volume: 20, Issue:2	Functional characterization of the basolateral rat liver organic anion transporting polypeptide.
AID682194	TP_TRANSPORTER: inhibition of Taurocholate uptake (CA: 200 uM) in membrane vesicles isolated from Mrp3-expressing LLC-PK1 cells	2000	The Journal of biological chemistry, Jan-28, Volume: 275, Issue:4	ATP-dependent transport of bile salts by rat multidrug resistance-associated protein 3 (Mrp3).
AID283565	Effect on uptake of [3H]estradiol in Escherichia coli CE1 with functional AcrAB-TolC system	2007	Antimicrobial agents and chemotherapy, Mar, Volume: 51, Issue:3	Substrate competition studies using whole-cell accumulation assays with the major tripartite multidrug efflux pumps of Escherichia coli.
AID680744	TP_TRANSPORTER: inhibition of E217betaG uptake (CA: 100 uM, E217betaG: 1 uM) in OATP-C-expressing HEK293 cells	2000	American journal of physiology. Gastrointestinal and liver physiology, Jan, Volume: 278, Issue:1	A novel human organic anion transporting polypeptide localized to the basolateral hepatocyte membrane.
AID682193	TP_TRANSPORTER: inhibition of Taurocholate uptake (E217betaG: 0.055 uM, TC: 206 uM) in membrane vesicles from LLC-PK1 cells	2000	The Journal of biological chemistry, Jan-28, Volume: 275, Issue:4	ATP-dependent transport of bile salts by rat multidrug resistance-associated protein 3 (Mrp3).
AID681720	TP_TRANSPORTER: uptake of Taurocholate at a concentration of 100 u M in membrane vesicles from Bsep-expressing Sf9 cells	2003	Journal of lipid research, Jan, Volume: 44, Issue:1	Physiological characteristics of allo-cholic acid.
AID680455	TP_TRANSPORTER: inhibition of LTC4 uptake (LTC4: 0.01uM, Taurocholate: 250 uM) in Xenopus laevis oocytes	1998	The Journal of biological chemistry, Jun-26, Volume: 273, Issue:26	Identification of glutathione as a driving force and leukotriene C4 as a substrate for oatp1, the hepatic sinusoidal organic solute transporter.
AID679652	TP_TRANSPORTER: uptake in membrane vesicles from MRP3-expressing HEK cells	2003	Biochemistry, Aug-26, Volume: 42, Issue:33	Characterization of the role of polar amino acid residues within predicted transmembrane helix 17 in determining the substrate specificity of multidrug resistance protein 3.
AID682021	TP_TRANSPORTER: Western in vivo, liver of C57BL/6J mouse	2002	Journal of hepatology, Nov, Volume: 37, Issue:5	Effects of bile salt flux variations on the expression of hepatic bile salt transporters in vivo in mice.
AID242619	Inhibition of dexamethasone-induced GR-mediated tyrosine amino transferase activity in rat hepatocytes; Not determined	2004	Bioorganic & medicinal chemistry letters, Aug-16, Volume: 14, Issue:16	Bile acid conjugates of a nonsteroidal glucocorticoid receptor modulator.
AID679995	TP_TRANSPORTER: uptake in Ntcp-expressing CHO cells	2003	Journal of lipid research, Jan, Volume: 44, Issue:1	Physiological characteristics of allo-cholic acid.
AID510559	Antibacterial activity against Escherichia coli AG102MB	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Single nucleotide polymorphism analysis of the major tripartite multidrug efflux pump of Escherichia coli: functional conservation in disparate animal reservoirs despite exposure to antimicrobial chemotherapy.
AID680228	TP_TRANSPORTER: uptake of Cholate at 20 uM in Oatp1-expressing HeLa cells	2003	American journal of physiology. Gastrointestinal and liver physiology, Nov, Volume: 285, Issue:5	Substrate specificities of rat oatp1 and ntcp: implications for hepatic organic anion uptake.
AID681228	TP_TRANSPORTER: inhibition of E1S uptake (E1S: 0.05 uM, CA: 5 uM) in Xenopus laevis oocytes	2001	Molecular pharmacology, May, Volume: 59, Issue:5	Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.
AID680623	TP_TRANSPORTER: inhibition of DNP-SG uptake (DNP-SG: 50 uM, Taurocholate: 250 uM) in Xenopus laevis oocytes	1998	The Journal of biological chemistry, Jun-26, Volume: 273, Issue:26	Identification of glutathione as a driving force and leukotriene C4 as a substrate for oatp1, the hepatic sinusoidal organic solute transporter.
AID682154	TP_TRANSPORTER: RT-PCR (mRNA level: reduction to 75 % of control) in vivo, liver of Him OF1 mouse	2001	Gastroenterology, Jul, Volume: 121, Issue:1	Effects of ursodeoxycholic and cholic acid feeding on hepatocellular transporter expression in mouse liver.
AID679151	TP_TRANSPORTER: uptake in Oatp2-expressing HeLa cells	2002	Hepatology (Baltimore, Md.), May, Volume: 35, Issue:5	Transport of the sulfated, amidated bile acid, sulfolithocholyltaurine, into rat hepatocytes is mediated by Oatp1 and Oatp2.
AID680349	TP_TRANSPORTER: inhibition of Digoxin uptake in Xenopus laevis oocytes	2001	The Journal of pharmacology and experimental therapeutics, Oct, Volume: 299, Issue:1	Multispecific substrate recognition of kidney-specific organic anion transporters OAT-K1 and OAT-K2.
AID679969	TP_TRANSPORTER: inhibition of Enalapril uptake in Oatp1-expressing HeLa cells	1998	Hepatology (Baltimore, Md.), Nov, Volume: 28, Issue:5	The modified dipeptide, enalapril, an angiotensin-converting enzyme inhibitor, is transported by the rat liver organic anion transport protein.
AID681389	TP_TRANSPORTER: inhibition of E217betaG uptake in membrane vesicles from MRP4-expressing HEK-293 cells	2003	The Biochemical journal, Apr-15, Volume: 371, Issue:Pt 2	Steroid and bile acid conjugates are substrates of human multidrug-resistance protein (MRP) 4 (ATP-binding cassette C4).
AID680434	TP_TRANSPORTER: inhibition of Ouabain uptake (Ouabain: 100 uM, TCA: 100 uM) in Xenopus laevis oocytes	1996	The Journal of pharmacology and experimental therapeutics, Mar, Volume: 276, Issue:3	Polyspecific drug and steroid clearance by an organic anion transporter of mammalian liver.
AID680450	TP_TRANSPORTER: inhibition of Ochratoxin A uptake (OTA: 1 uM, TCA: 100uM) in Xenopus laevis oocytes	1996	The Journal of pharmacology and experimental therapeutics, Dec, Volume: 279, Issue:3	Uptake of the mycotoxin ochratoxin A in liver cells occurs via the cloned organic anion transporting polypeptide.
AID680044	TP_TRANSPORTER: uptake of Taurocholate at 20 u M in Oatp1-expressing CHO cells	2003	Journal of lipid research, Jan, Volume: 44, Issue:1	Physiological characteristics of allo-cholic acid.
AID682195	TP_TRANSPORTER: inhibition of F-MTX uptake (F-MTX: 5.0 uM, TC: 200.0 uM) in membrane vesicles from Mrp3-Sf9 cells	2003	American journal of physiology. Gastrointestinal and liver physiology, Sep, Volume: 285, Issue:3	Transport of fluorescein methotrexate by multidrug resistance-associated protein 3 in IEC-6 cells.
AID680257	TP_TRANSPORTER: inhibition of Taurocholate uptake (Taurochorate: 20 uM, CA: 200 uM) in Xenopus laevis oocytes	1994	Hepatology (Baltimore, Md.), Aug, Volume: 20, Issue:2	Functional characterization of the basolateral rat liver organic anion transporting polypeptide.
AID283564	Effect on uptake of [3H]estradiol in Escherichia coli AG102 with functional AcrAB-TolC system	2007	Antimicrobial agents and chemotherapy, Mar, Volume: 51, Issue:3	Substrate competition studies using whole-cell accumulation assays with the major tripartite multidrug efflux pumps of Escherichia coli.
AID1802450	Oatp1d1 Transport Assay from Article 10.1074/jbc.M113.518506: \\Molecular characterization of zebrafish Oatp1d1 (Slco1d1), a novel organic anion-transporting polypeptide.\\	2013	The Journal of biological chemistry, Nov-22, Volume: 288, Issue:47	Molecular characterization of zebrafish Oatp1d1 (Slco1d1), a novel organic anion-transporting polypeptide.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1449 (39.81)	18.7374
1990's	891 (24.48)	18.2507
2000's	579 (15.91)	29.6817
2010's	610 (16.76)	24.3611
2020's	111 (3.05)	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	26 (0.69%)	5.53%
Reviews	54 (1.43%)	6.00%
Case Studies	8 (0.21%)	4.05%
Observational	3 (0.08%)	0.25%
Other	3,698 (97.60%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
dinitrochlorobenzene Dinitrochlorobenzene: A skin irritant that may cause dermatitis of both primary and allergic types. Contact sensitization with DNCB has been used as a measure of cellular immunity. DNCB is also used as a reagent for the detection and determination of pyridine compounds.. 1-chloro-2,4-dinitrobenzene : A C-nitro compound that is chlorobenzene carrying a nitro substituent at each of the 2- and 4-positions.	1.95	1	0	C-nitro compound; monochlorobenzenes	allergen; epitope; sensitiser
alpha-ketoglutaric acid 2-oxoglutaric acid : An oxo dicarboxylic acid that consists of glutaric acid bearing an oxo substituent at position 2. It is an intermediate metabolite in Krebs cycle.	2.4	2	0	oxo dicarboxylic acid	fundamental metabolite
gamma-aminobutyric acid gamma-Aminobutyric Acid: The most common inhibitory neurotransmitter in the central nervous system.. gamma-aminobutyric acid : A gamma-amino acid that is butanoic acid with the amino substituent located at C-4.	2.37	2	0	amino acid zwitterion; gamma-amino acid; monocarboxylic acid	human metabolite; neurotransmitter; Saccharomyces cerevisiae metabolite; signalling molecule
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.	3.15	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
ethylene glycol Ethylene Glycol: A colorless, odorless, viscous dihydroxy alcohol. It has a sweet taste, but is poisonous if ingested. Ethylene glycol is the most important glycol commercially available and is manufactured on a large scale in the United States. It is used as an antifreeze and coolant, in hydraulic fluids, and in the manufacture of low-freezing dynamites and resins.. ethanediol : Any diol that is ethane or substituted ethane carrying two hydroxy groups.. ethylene glycol : A 1,2-glycol compound produced via reaction of ethylene oxide with water.	1.97	1	0	ethanediol; glycol	metabolite; mouse metabolite; solvent; toxin
acetic acid Acetic Acid: Product of the oxidation of ethanol and of the destructive distillation of wood. It is used locally, occasionally internally, as a counterirritant and also as a reagent. (Stedman, 26th ed). acetic acid : A simple monocarboxylic acid containing two carbons.	7.9	4	0	monocarboxylic acid	antimicrobial food preservative; Daphnia magna metabolite; food acidity regulator; protic solvent
acetaldehyde Acetaldehyde: A colorless, flammable liquid used in the manufacture of acetic acid, perfumes, and flavors. It is also an intermediate in the metabolism of alcohol. It has a general narcotic action and also causes irritation of mucous membranes. Large doses may cause death from respiratory paralysis.. acetaldehyde : The aldehyde formed from acetic acid by reduction of the carboxy group. It is the most abundant carcinogen in tobacco smoke.. aldehyde : A compound RC(=O)H, in which a carbonyl group is bonded to one hydrogen atom and to one R group.. acetyl group : A group, formally derived from acetic acid by dehydroxylation, which is fundamental to the biochemistry of all forms of life. When bound to coenzyme A, it is central to the metabolism of carbohydrates and fats.	2.39	2	0	aldehyde	carcinogenic agent; EC 3.5.1.4 (amidase) inhibitor; electron acceptor; Escherichia coli metabolite; human metabolite; mouse metabolite; mutagen; oxidising agent; Saccharomyces cerevisiae metabolite; teratogenic agent
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	4.6	6	0	ketone body; methyl ketone; propanones; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; human metabolite; polar aprotic solvent
adenine [no description available]	2.75	3	0	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
ammonium hydroxide azane : Saturated acyclic nitrogen hydrides having the general formula NnHn+2.	2.39	2	0	azane; gas molecular entity; mononuclear parent hydride	EC 3.5.1.4 (amidase) inhibitor; metabolite; mouse metabolite; neurotoxin; NMR chemical shift reference compound; nucleophilic reagent; refrigerant
arsenic acid arsenic acid: RN given refers to orthoarsenic acid(H3AsO4); see also sodium arsenate. arsenic acid : An arsenic oxoacid comprising one oxo group and three hydroxy groups attached to a central arsenic atom.	2.03	1	0	arsenic oxoacid	Escherichia coli metabolite
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.	2.39	2	0	benzoic acids	algal metabolite; antimicrobial food preservative; drug allergen; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 3.1.1.3 (triacylglycerol lipase) inhibitor; human xenobiotic metabolite; plant metabolite
betaine glycine betaine : The amino acid betaine derived from glycine.	2.44	2	0	amino-acid betaine; glycine derivative	fundamental metabolite
bromide Bromides: Salts of hydrobromic acid, HBr, with the bromine atom in the 1- oxidation state. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	2.01	1	0	halide anion; monoatomic bromine
1-butanol 1-Butanol: A four carbon linear hydrocarbon that has a hydroxy group at position 1.. butan-1-ol : A primary alcohol that is butane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It it produced in small amounts in humans by the gut microbes.	2.67	3	0	alkyl alcohol; primary alcohol; short-chain primary fatty alcohol	human metabolite; mouse metabolite; protic solvent
butyric acid Butyric Acid: A four carbon acid, CH3CH2CH2COOH, with an unpleasant odor that occurs in butter and animal fat as the glycerol ester.. butyrate : A short-chain fatty acid anion that is the conjugate base of butyric acid, obtained by deprotonation of the carboxy group.. butyric acid : A straight-chain saturated fatty acid that is butane in which one of the terminal methyl groups has been oxidised to a carboxy group.	1.99	1	0	fatty acid 4:0; straight-chain saturated fatty acid	human urinary metabolite; Mycoplasma genitalium metabolite
carbamates [no description available]	1.95	1	0	amino-acid anion
carbon monoxide Carbon Monoxide: Carbon monoxide (CO). A poisonous colorless, odorless, tasteless gas. It combines with hemoglobin to form carboxyhemoglobin, which has no oxygen carrying capacity. The resultant oxygen deprivation causes headache, dizziness, decreased pulse and respiratory rates, unconsciousness, and death. (From Merck Index, 11th ed). carbon monoxide : A one-carbon compound in which the carbon is joined only to a single oxygen. It is a colourless, odourless, tasteless, toxic gas.	4.18	5	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
carnitine [no description available]	3.15	5	0	amino-acid betaine	human metabolite; mouse metabolite
catechol [no description available]	1.97	1	0	catechols	allelochemical; genotoxin; plant metabolite
chlordecone [no description available]	2.88	4	0	cyclic ketone; organochlorine compound	insecticide; persistent organic pollutant
choline [no description available]	4.76	12	0	cholines	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter; nutrient; plant metabolite; Saccharomyces cerevisiae metabolite
citric acid, anhydrous Citric Acid: A key intermediate in metabolism. It is an acid compound found in citrus fruits. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability.. citric acid : A tricarboxylic acid that is propane-1,2,3-tricarboxylic acid bearing a hydroxy substituent at position 2. It is an important metabolite in the pathway of all aerobic organisms.	2.48	2	0	tricarboxylic acid	antimicrobial agent; chelator; food acidity regulator; fundamental metabolite
chlorine chloride : A halide anion formed when chlorine picks up an electron to form an an anion.	5.07	44	0	halide anion; monoatomic chlorine	cofactor; Escherichia coli metabolite; human metabolite
hydrochloric acid Hydrochloric Acid: A strong corrosive acid that is commonly used as a laboratory reagent. It is formed by dissolving hydrogen chloride in water. GASTRIC ACID is the hydrochloric acid component of GASTRIC JUICE.. hydrogen chloride : A mononuclear parent hydride consisting of covalently bonded hydrogen and chlorine atoms.	9.83	34	0	chlorine molecular entity; gas molecular entity; hydrogen halide; mononuclear parent hydride	mouse metabolite
coumarin 2H-chromen-2-one: coumarin derivative	2.07	1	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).	2.91	4	0	monohydroxybenzoic acid	algal metabolite; antifungal agent; antiinfective agent; EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor; keratolytic drug; plant hormone; plant metabolite
hydrogen sulfide Hydrogen Sulfide: A flammable, poisonous gas with a characteristic odor of rotten eggs. It is used in the manufacture of chemicals, in metallurgy, and as an analytical reagent. (From Merck Index, 11th ed). hydrogen sulfide : A sulfur hydride consisting of a single sulfur atom bonded to two hydrogen atoms. A highly poisonous, flammable gas with a characteristic odour of rotten eggs, it is often produced by bacterial decomposition of organic matter in the absence of oxygen.. thiol : An organosulfur compound in which a thiol group, -SH, is attached to a carbon atom of any aliphatic or aromatic moiety.	3.68	2	0	gas molecular entity; hydracid; mononuclear parent hydride; sulfur hydride	Escherichia coli metabolite; genotoxin; metabolite; signalling molecule; toxin; vasodilator agent
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.	2.75	3	0	aromatic ketone; monochlorobenzenes; secondary amino compound	antidepressant; environmental contaminant; xenobiotic
hippuric acid hippuric acid: RN given refers to parent cpd; structure in Merck Index, 9th ed, #4591. N-benzoylglycine : An N-acylglycine in which the acyl group is specified as benzoyl.	1.96	1	0	N-acylglycine	human blood serum metabolite; uremic toxin
malic acid malic acid : A 2-hydroxydicarboxylic acid that is succinic acid in which one of the hydrogens attached to a carbon is replaced by a hydroxy group.. 2-hydroxydicarboxylic acid : Any dicarboxylic acid carrying a hydroxy group on the carbon atom at position alpha to the carboxy group.	1.99	1	0	2-hydroxydicarboxylic acid; C4-dicarboxylic acid	food acidity regulator; fundamental metabolite
3,4-dihydroxyphenylacetic acid 3,4-Dihydroxyphenylacetic Acid: A deaminated metabolite of LEVODOPA.. (3,4-dihydroxyphenyl)acetic acid : A dihydroxyphenylacetic acid having the two hydroxy substituents located at the 3- and 4-positions. It is a metabolite of dopamine.. dihydroxyphenylacetic acid : A dihydroxy monocarboxylic acid consisting of phenylacetic acid having two phenolic hydroxy substituents.	2.1	1	0	catechols; dihydroxyphenylacetic acid	human metabolite
lactic acid Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.	3.45	7	0	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
dimethyl sulfoxide Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.	4.69	9	0	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
formaldehyde paraform: polymerized formaldehyde; RN given refers to parent cpd; used in root canal therapy	1.97	1	0	aldehyde; one-carbon compound	allergen; carcinogenic agent; disinfectant; EC 3.5.1.4 (amidase) inhibitor; environmental contaminant; Escherichia coli metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
glutaric acid glutaric acid: RN given refers to parent cpd. glutaric acid : An alpha,omega-dicarboxylic acid that is a linear five-carbon dicarboxylic acid.	2.7	3	0	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	Daphnia magna metabolite; human metabolite
glycine [no description available]	5.23	51	0	alpha-amino acid; amino acid zwitterion; proteinogenic amino acid; serine family amino acid	EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor; fundamental metabolite; hepatoprotective agent; micronutrient; neurotransmitter; NMDA receptor agonist; nutraceutical
glycerol Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.	8.83	12	0	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
alpha-glycerophosphoric acid [no description available]	2.4	2	0	glycerol monophosphate	algal metabolite; human metabolite
glycolic acid glycolic acid: RN given refers to parent cpd. glycolic acid : A 2-hydroxy monocarboxylic acid that is acetic acid where the methyl group has been hydroxylated.	2.13	1	0	2-hydroxy monocarboxylic acid; primary alcohol	keratolytic drug; metabolite
hydrogen carbonate Bicarbonates: Inorganic salts that contain the -HCO3 radical. They are an important factor in determining the pH of the blood and the concentration of bicarbonate ions is regulated by the kidney. Levels in the blood are an index of the alkali reserve or buffering capacity.. hydrogencarbonate : The carbon oxoanion resulting from the removal of a proton from carbonic acid.	6.57	66	0	carbon oxoanion	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
histamine [no description available]	3.67	10	0	aralkylamino compound; imidazoles	human metabolite; mouse metabolite; neurotransmitter
hydrogen Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.	4.17	17	0	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
methanol Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.	1.95	1	0	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
inositol Inositol: An isomer of glucose that has traditionally been considered to be a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in man. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1379) Inositol phospholipids are important in signal transduction.. inositol : Any cyclohexane-1,2,3,4,5,6-hexol.. 1D-chiro-inositol : Belonging to the inositol family of compounds, D-chiro-inositol (DCI) is an isomer of glucose. It is an important secondary messenger in insulin signal transduction.. muco-inositol : An inositol that is cyclohexane-1,2,3,4,5,6-hexol having a (1R,2R,3r,4R,5S,6r)-configuration.	3.36	7	0	cyclitol; hexol
melatonin [no description available]	3.58	8	0	acetamides; tryptamines	anticonvulsant; central nervous system depressant; geroprotector; hormone; human metabolite; immunological adjuvant; mouse metabolite; radical scavenger
naphthalene [no description available]	2.06	1	0	naphthalenes; ortho-fused bicyclic arene	apoptosis inhibitor; carcinogenic agent; environmental contaminant; mouse metabolite; plant metabolite; volatile oil component
nickel Nickel: A trace element with the atomic symbol Ni, atomic number 28, and atomic weight 58.69. It is a cofactor of the enzyme UREASE.. nickel ion : A nickel atom having a net electric charge.. nickel atom : Chemical element (nickel group element atom) with atomic number 28.	2.1	1	0	metal allergen; nickel group element atom	epitope; micronutrient
niacinamide nicotinamide : A pyridinecarboxamide that is pyridine in which the hydrogen at position 3 is replaced by a carboxamide group.	2.42	2	0	pyridine alkaloid; pyridinecarboxamide; vitamin B3	anti-inflammatory agent; antioxidant; cofactor; EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; Escherichia coli metabolite; geroprotector; human urinary metabolite; metabolite; mouse metabolite; neuroprotective agent; Saccharomyces cerevisiae metabolite; Sir2 inhibitor
niacin Niacin: A water-soluble vitamin of the B complex occurring in various animal and plant tissues. It is required by the body for the formation of coenzymes NAD and NADP. It has PELLAGRA-curative, vasodilating, and antilipemic properties.. vitamin B3 : Any member of a group of vitamers that belong to the chemical structural class called pyridines that exhibit biological activity against vitamin B3 deficiency. Vitamin B3 deficiency causes a condition known as pellagra whose symptoms include depression, dermatitis and diarrhea. The vitamers include nicotinic acid and nicotinamide (and their ionized and salt forms).. nicotinic acid : A pyridinemonocarboxylic acid that is pyridine in which the hydrogen at position 3 is replaced by a carboxy group.	2.44	2	0	pyridine alkaloid; pyridinemonocarboxylic acid; vitamin B3	antidote; antilipemic drug; EC 3.5.1.19 (nicotinamidase) inhibitor; Escherichia coli metabolite; human urinary metabolite; metabolite; mouse metabolite; plant metabolite; vasodilator agent
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	3.25	6	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
nitrites Nitrites: Salts of nitrous acid or compounds containing the group NO2-. The inorganic nitrites of the type MNO2 (where M=metal) are all insoluble, except the alkali nitrites. The organic nitrites may be isomeric, but not identical with the corresponding nitro compounds. (Grant & Hackh's Chemical Dictionary, 5th ed)	3.11	5	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species	human metabolite
1-octanol 1-Octanol: A colorless, slightly viscous liquid used as a defoaming or wetting agent. It is also used as a solvent for protective coatings, waxes, and oils, and as a raw material for plasticizers. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). octan-1-ol : An octanol carrying the hydroxy group at position 1.	2.08	1	0	octanol; primary alcohol	antifungal agent; bacterial metabolite; fuel additive; kairomone; plant metabolite
oxalic acid Oxalic Acid: A strong dicarboxylic acid occurring in many plants and vegetables. It is produced in the body by metabolism of glyoxylic acid or ascorbic acid. It is not metabolized but excreted in the urine. It is used as an analytical reagent and general reducing agent.. oxalic acid : An alpha,omega-dicarboxylic acid that is ethane substituted by carboxyl groups at positions 1 and 2.	1.96	1	0	alpha,omega-dicarboxylic acid	algal metabolite; human metabolite; plant metabolite
4-aminobenzoic acid 4-Aminobenzoic Acid: An aminobenzoic acid isomer that combines with pteridine and GLUTAMIC ACID to form FOLIC ACID. The fact that 4-aminobenzoic acid absorbs light throughout the UVB range has also resulted in its use as an ingredient in SUNSCREENS.. 4-ammoniobenzoate : A zwitterion obtained by transfer of a proton from the carboxy to the amino group of 4-aminobenzoic acid.. 4-aminobenzoic acid : An aminobenzoic acid in which the amino group is para to the carboxy group.	1.95	1	0	aminobenzoic acid; aromatic amino-acid zwitterion	allergen; Escherichia coli metabolite; plant metabolite
palmitic acid Palmitic Acid: A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids.. hexadecanoic acid : A straight-chain, sixteen-carbon, saturated long-chain fatty acid.	2.89	4	0	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; EC 1.1.1.189 (prostaglandin-E2 9-reductase) inhibitor; plant metabolite
phenol [no description available]	2.42	2	0	phenols	antiseptic drug; disinfectant; human xenobiotic metabolite; mouse metabolite
phosphoenolpyruvate Phosphoenolpyruvate: A monocarboxylic acid anion derived from selective deprotonation of the carboxy group of phosphoenolpyruvic acid. It is a metabolic intermediate in GLYCOLYSIS; GLUCONEOGENESIS; and other pathways.. phosphoenolpyruvate : A monocarboxylic acid anion resuting from selective deprotonation of the carboxy group of phosphoenolpyruvic acid.. phosphoenolpyruvic acid : A monocarboxylic acid that is acrylic acid substituted by a phosphonooxy group at position 2. It is a metabolic intermediate in pathways like glycolysis and gluconeogenesis.	1.95	1	0	carboxyalkyl phosphate; monocarboxylic acid	fundamental metabolite
propionic acid propionic acid : A short-chain saturated fatty acid comprising ethane attached to the carbon of a carboxy group.	2.38	2	0	saturated fatty acid; short-chain fatty acid	antifungal drug
pyridoxine 4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol: structure in first source. vitamin B6 : Any member of the group of pyridines that exhibit biological activity against vitamin B6 deficiency. Vitamin B6 deficiency is associated with microcytic anemia, electroencephalographic abnormalities, dermatitis with cheilosis (scaling on the lips and cracks at the corners of the mouth) and glossitis (swollen tongue), depression and confusion, and weakened immune function. Vitamin B6 consists of the vitamers pyridoxine, pyridoxal, and pyridoxamine and their respective 5'-phosphate esters (and includes their corresponding ionized and salt forms).	1.94	1	0	hydroxymethylpyridine; methylpyridines; monohydroxypyridine; vitamin B6	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
pyrogallol benzenetriol : A triol in which three hydroxy groups are substituted onto a benzene ring.	1.97	1	0	benzenetriol; phenolic donor	plant metabolite
pyruvic acid Pyruvic Acid: An intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed). pyruvic acid : A 2-oxo monocarboxylic acid that is the 2-keto derivative of propionic acid. It is a metabolite obtained during glycolysis.	2	1	0	2-oxo monocarboxylic acid	cofactor; fundamental metabolite
sarcosine cocobetaine: N-alkyl-betaine; cause of shampoo dermatitis	2.38	2	0	N-alkylglycine zwitterion; N-alkylglycine; N-methyl-amino acid; N-methylglycines	Escherichia coli metabolite; glycine receptor agonist; glycine transporter 1 inhibitor; human metabolite; mouse metabolite
sulfites Sulfites: Inorganic salts of sulfurous acid.. sulfites : Any sulfurous acid derivative that is a salt or an ester of sulfurous acid.. organosulfonate oxoanion : An organic anion obtained by deprotonation of the sufonate group(s) of any organosulfonic acid.. sulfite : A sulfur oxoanion that is the conjugate base of hydrogen sulfite (H2SO3).	2.07	1	0	divalent inorganic anion; sulfur oxide; sulfur oxoanion
spermidine [no description available]	2.39	2	0	polyazaalkane; triamine	autophagy inducer; fundamental metabolite; geroprotector
spermine [no description available]	3.33	6	0	polyazaalkane; tetramine	antioxidant; fundamental metabolite; immunosuppressive agent
succinic acid Succinic Acid: A water-soluble, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. (Hawley's Condensed Chemical Dictionary, 12th ed, p1099; McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed, p1851). succinic acid : An alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle.	2	1	0	alpha,omega-dicarboxylic acid; C4-dicarboxylic acid	anti-ulcer drug; fundamental metabolite; micronutrient; nutraceutical; radiation protective agent
taurine [no description available]	8.35	98	1	amino sulfonic acid; zwitterion	antioxidant; Escherichia coli metabolite; glycine receptor agonist; human metabolite; mouse metabolite; nutrient; radical scavenger; Saccharomyces cerevisiae metabolite
thiamine thiamine(1+) : A primary alcohol that is 1,3-thiazol-3-ium substituted by (4-amino-2-methylpyrimidin-5-yl)methyl, methyl and 2-hydroxyethyl groups at positions 3, 4 and 5, respectively.	2.67	3	0	primary alcohol; vitamin B1	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
toluene methylbenzene : Any alkylbenzene that is benzene substituted with one or more methyl groups.	2.37	2	0	methylbenzene; toluenes; volatile organic compound	cholinergic antagonist; fuel additive; neurotoxin; non-polar solvent
uracil 2,4-dihydroxypyrimidine: a urinary biomarker for bipolar disorder	2.15	1	0	pyrimidine nucleobase; pyrimidone	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; prodrug; Saccharomyces cerevisiae metabolite
uric acid Uric Acid: An oxidation product, via XANTHINE OXIDASE, of oxypurines such as XANTHINE and HYPOXANTHINE. It is the final oxidation product of purine catabolism in humans and primates, whereas in most other mammals URATE OXIDASE further oxidizes it to ALLANTOIN.. uric acid : An oxopurine that is the final oxidation product of purine metabolism.. 6-hydroxy-1H-purine-2,8(7H,9H)-dione : A tautomer of uric acid having oxo groups at C-2 and C-8 and a hydroxy group at C-6.. 7,9-dihydro-1H-purine-2,6,8(3H)-trione : An oxopurine in which the purine ring is substituted by oxo groups at positions 2, 6, and 8.	3.1	5	0	uric acid	Escherichia coli metabolite; human metabolite; mouse metabolite
urea pseudourea: clinical use; structure. isourea : A carboximidic acid that is the imidic acid tautomer of urea, H2NC(=NH)OH, and its hydrocarbyl derivatives.	3.99	14	0	isourea; monocarboxylic acid amide; one-carbon compound	Daphnia magna metabolite; Escherichia coli metabolite; fertilizer; flour treatment agent; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
isocitric acid isocitric acid: RN given refers to unlabeled parent cpd. isocitric acid : A tricarboxylic acid that is propan-1-ol with a hydrogen at each of the 3 carbon positions replaced by a carboxy group.	2.11	1	0	secondary alcohol; tricarboxylic acid	fundamental metabolite
bremazocine [no description available]	2.06	1	0
1-anilino-8-naphthalenesulfonate 1-anilino-8-naphthalenesulfonate: RN given refers to parent cpd. 8-anilinonaphthalene-1-sulfonic acid : A naphthalenesulfonic acid that is naphthalene-1-sulfonic acid substituted by a phenylamino group at position 8.	7.24	127	0	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
hoe 33342 BXI-72: structure in first source	2.46	2	0	bibenzimidazole; N-methylpiperazine	fluorochrome
2,4-dinitrophenol 2,4-Dinitrophenol: A toxic dye, chemically related to trinitrophenol (picric acid), used in biochemical studies of oxidative processes where it uncouples oxidative phosphorylation. It is also used as a metabolic stimulant. (Stedman, 26th ed). dinitrophenol : Members of the class of nitrophenol carrying two nitro substituents.. 2,4-dinitrophenol : A dinitrophenol having the nitro groups at the 2- and 4-positions.	2.4	2	0	dinitrophenol	allergen; antiseptic drug; bacterial xenobiotic metabolite; geroprotector; oxidative phosphorylation inhibitor
mercaptoethanol Mercaptoethanol: A water-soluble thiol derived from hydrogen sulfide and ethanol. It is used as a reducing agent for disulfide bonds and to protect sulfhydryl groups from oxidation.	1.95	1	0	alkanethiol; primary alcohol	geroprotector
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.	2.02	1	0	organoboron compound; primary amino compound	calcium channel blocker; IP3 receptor antagonist; potassium channel opener
3-aminobenzamide [no description available]	2.96	4	0	benzamides; substituted aniline	EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor
3-methylcholanthrene Methylcholanthrene: A carcinogen that is often used in experimental cancer studies.. 3-methylcholanthrene : A pentacyclic ortho- and peri-fused polycyclic arene consisting of a dihydrocyclopenta[ij]tetraphene ring system with a methyl substituent at the 3-position.	1.95	1	0	ortho- and peri-fused polycyclic arene	aryl hydrocarbon receptor agonist; carcinogenic agent
(4-amidinophenyl)methanesulfonyl fluoride [no description available]	1.98	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.	2.45	2	0	guaiacols; monocarboxylic acid	human metabolite; mouse metabolite
phenytoin [no description available]	3.11	5	0	imidazolidine-2,4-dione	anticonvulsant; drug allergen; sodium channel blocker; teratogenic agent
hydroxyindoleacetic acid (5-hydroxyindol-3-yl)acetic acid : A member of the class of indole-3-acetic acids that is indole-3-acetic acid substituted by a hydroxy group at C-5.	2.37	2	0	indole-3-acetic acids	drug metabolite; human metabolite; mouse metabolite
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.	2.13	1	0	acridines; aromatic amine	EC 3.1.1.7 (acetylcholinesterase) inhibitor
acebutolol Acebutolol: A cardioselective beta-1 adrenergic antagonist with little effect on the bronchial receptors. The drug has stabilizing and quinidine-like effects on cardiac rhythm, as well as weak inherent sympathomimetic action.. acebutolol : An ether that is the 2-acetyl-4-(butanoylamino)phenyl ether of the primary hydroxy group of 3-(propan-2-ylamino)propane-1,2-diol.	2.06	1	0	aromatic amide; ethanolamines; ether; monocarboxylic acid amide; propanolamine; secondary amino compound	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; sympathomimetic agent
acetaminophen Acetaminophen: Analgesic antipyretic derivative of acetanilide. It has weak anti-inflammatory properties and is used as a common analgesic, but may cause liver, blood cell, and kidney damage.. paracetamol : A member of the class of phenols that is 4-aminophenol in which one of the hydrogens attached to the amino group has been replaced by an acetyl group.	3.49	8	0	acetamides; phenols	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; cyclooxygenase 3 inhibitor; environmental contaminant; ferroptosis inducer; geroprotector; hepatotoxic agent; human blood serum metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
acetazolamide Acetazolamide: One of the CARBONIC ANHYDRASE INHIBITORS that is sometimes effective against absence seizures. It is sometimes useful also as an adjunct in the treatment of tonic-clonic, myoclonic, and atonic seizures, particularly in women whose seizures occur or are exacerbated at specific times in the menstrual cycle. However, its usefulness is transient often because of rapid development of tolerance. Its antiepileptic effect may be due to its inhibitory effect on brain carbonic anhydrase, which leads to an increased transneuronal chloride gradient, increased chloride current, and increased inhibition. (From Smith and Reynard, Textbook of Pharmacology, 1991, p337)	3.35	7	0	monocarboxylic acid amide; sulfonamide; thiadiazoles	anticonvulsant; diuretic; EC 4.2.1.1 (carbonic anhydrase) inhibitor
albendazole [no description available]	1.97	1	0	aryl sulfide; benzimidazoles; benzimidazolylcarbamate fungicide; carbamate ester	anthelminthic drug; microtubule-destabilising agent; tubulin modulator
albuterol Albuterol: A short-acting beta-2 adrenergic agonist that is primarily used as a bronchodilator agent to treat ASTHMA. Albuterol is prepared as a racemic mixture of R(-) and S(+) stereoisomers. The stereospecific preparation of R(-) isomer of albuterol is referred to as levalbuterol.. albuterol : A member of the class of phenylethanolamines that is 4-(2-amino-1-hydroxyethyl)-2-(hydroxymethyl)phenol having a tert-butyl group attached to the nirogen atom. It acts as a beta-adrenergic agonist used in the treatment of asthma and chronic obstructive pulmonary disease (COPD).	1.97	1	0	phenols; phenylethanolamines; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; environmental contaminant; xenobiotic
alendronate alendronic acid : A 1,1-bis(phosphonic acid) that is methanebis(phosphonic acid) in which the two methylene hydrogens are replaced by hydroxy and 3-aminopropyl groups.	2.05	1	0	1,1-bis(phosphonic acid); primary amino compound	bone density conservation agent; EC 2.5.1.1 (dimethylallyltranstransferase) inhibitor
alminoprofen alminoprofen: structure given in first source; RN given refers to parent cpd without isomeric designation. alminoprofen : A substituted aniline that is ibuprofen in which the isobutyl group is replaced by a (2-methylprop-2-en-1-yl)amino group. A non-steroidal anti-inflammatory drug, it is used for treatment of inflammatory and rheumatic disorders.	2.06	1	0	amino acid; monocarboxylic acid; secondary amino compound; substituted aniline	antipyretic; antirheumatic drug; cyclooxygenase 2 inhibitor; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; EC 3.1.1.4 (phospholipase A2) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
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.	2.01	1	0	organochlorine compound; triazolobenzodiazepine	anticonvulsant; anxiolytic drug; GABA agonist; muscle relaxant; sedative; xenobiotic
alprenolol Alprenolol: One of the ADRENERGIC BETA-ANTAGONISTS used as an antihypertensive, anti-anginal, and anti-arrhythmic agent.. alprenolol : A secondary alcohol that is propan-2-ol substituted by a 2-allylphenoxy group at position 1 and an isopropylamino group at position 3. It is a beta-adrenergic antagonist used as a antihypertensive, anti-arrhythmia and a sympatholytic agent.	2.06	1	0	secondary alcohol; secondary amino compound	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; sympatholytic agent
am 251 AM 251: an analog of SR141716A; structure given in first source. AM-251 : A carbohydrazide obtained by formal condensation of the carboxy group of 1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid with the amino group of 1-aminopiperidine. An antagonist at the CB1 cannabinoid receptor.	2.02	1	0	amidopiperidine; carbohydrazide; dichlorobenzene; organoiodine compound; pyrazoles	antidepressant; antineoplastic agent; apoptosis inducer; CB1 receptor antagonist
amantadine amant: an antiviral compound consisting of an adamantane derivative chemically linked to a water-solube polyanioic matrix; structure in first source	3.85	3	0	adamantanes; primary aliphatic amine	analgesic; antiparkinson drug; antiviral drug; dopaminergic agent; NMDA receptor antagonist; non-narcotic analgesic
amfenac amfenac: RN given refers to parent cpd; structure. amfenac : An oxo monocarboxylic acid that is benzophenone in which one of the phenyl groups is substituted by an amino group and a carboxymethyl group at position 2 and 3, respectively. The corresponding carboxamide, nepafenac, is a prodrug of amfenac and is used for the treatment of pain and inflammation following cataract surgery.	2.06	1	0	amino acid; benzophenones; oxo monocarboxylic acid; primary amino compound; substituted aniline	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
diatrizoic acid Diatrizoate: A commonly used x-ray contrast medium. As DIATRIZOATE MEGLUMINE and as Diatrizoate sodium, it is used for gastrointestinal studies, angiography, and urography.. amidotrizoic acid : A member of the class of benzoic acids that is benzoic acid having iodo substituents at the 2-, 4- and 6-positions and acetamido substituents at the 3- and 5-positions. It is used, mainly as its N-methylglucamine and sodium salts, as an X-ray contrast medium in gastrointestinal studies, angiography, and urography.	1.98	1	0	acetamides; benzoic acids; organoiodine compound	environmental contaminant; radioopaque medium; xenobiotic
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.	1.98	1	0	guanidines; one-carbon compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor; EC 1.4.3.4 (monoamine oxidase) inhibitor
p-aminohippuric acid p-Aminohippuric Acid: The glycine amide of 4-aminobenzoic acid. Its sodium salt is used as a diagnostic aid to measure effective renal plasma flow (ERPF) and excretory capacity.. p-aminohippurate : A hippurate that is the conjugate base of p-aminohippuric acid, arising from deprotonation of the carboxy group.. p-aminohippuric acid : An N-acylglycine that is the 4-amino derivative of hippuric acid; used as a diagnostic agent in the measurement of renal plasma flow.	5.67	25	0	N-acylglycine	Daphnia magna metabolite
theophylline [no description available]	3.92	13	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.	3.12	5	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.	2.46	2	0	carbotricyclic compound; tertiary amine	adrenergic uptake inhibitor; antidepressant; environmental contaminant; tropomyosin-related kinase B receptor agonist; xenobiotic
amlodipine Amlodipine: A long-acting dihydropyridine calcium channel blocker. It is effective in the treatment of ANGINA PECTORIS and HYPERTENSION.. amlodipine : A fully substituted dialkyl 1,4-dihydropyridine-3,5-dicarboxylate derivative, which is used for the treatment of hypertension, chronic stable angina and confirmed or suspected vasospastic angina.	2.03	1	0	dihydropyridine; ethyl ester; methyl ester; monochlorobenzenes; primary amino compound	antihypertensive agent; calcium channel blocker; vasodilator agent
antazoline Antazoline: An antagonist of histamine H1 receptors.. antazoline : A member of the class of imidazolines that is 2-aminomethyl-2-imidazoline in which the exocyclic amino hydrogens are replaced by benzyl and phenyl groups. Antazoline is only found in individuals that have taken the drug.	1.95	1	0	aromatic amine; imidazolines; tertiary amino compound	cholinergic antagonist; H1-receptor antagonist; xenobiotic
antipyrine Antipyrine: An analgesic and antipyretic that has been given by mouth and as ear drops. Antipyrine is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver. (From Martindale, The Extra Pharmacopoeia, 30th ed, p29). antipyrine : A pyrazolone derivative that is 1,2-dihydropyrazol-3-one substituted with methyl groups at N-1 and C-5 and with a phenyl group at N-2.	3.37	7	0	pyrazolone	antipyretic; cyclooxygenase 3 inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
arotinolol arotinolol: structure given in first source; arotinolol is the (+-)-isomer	2.01	1	0	aromatic amide; thiophenes
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.	5.37	59	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.	2.46	2	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.	2.72	3	0	ethanolamines; monocarboxylic acid amide; propanolamine	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; environmental contaminant; sympatholytic agent; xenobiotic
azelastine azelastine: azeptin is azelastine hydrochloride; structure; eye drop formulation effective in relieving symptoms of allergic conjunctivitis; do not confuse with 5-loxin which is an extract of Boswellia. azelastine : A phthalazine compound having an oxo substituent at the 1-position, a 1-methylazepan-4-yl group at the 2-position and a 4-chlorobenzyl substituent at the 4-position.	3.51	1	0	monochlorobenzenes; phthalazines; tertiary amino compound	anti-allergic agent; anti-asthmatic drug; bronchodilator agent; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; H1-receptor antagonist; platelet aggregation inhibitor
benzamide benzamide : An aromatic amide that consists of benzene bearing a single carboxamido substituent. The parent of the class of benzamides.	2.05	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.	2.96	4	0	1-benzofurans; aromatic ketone	uricosuric drug
berberine [no description available]	3.25	5	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
2,5-di-tert-butylhydroquinone 2,5-di-tert-butylbenzene-1,4-diol : A member of the class of hydroquinones that is benzene-1,4-diol substituted by tert-butyl groups at position 2 and 5.	2.02	1	0	hydroquinones
bisacodyl Bisacodyl: A diphenylmethane stimulant laxative used for the treatment of CONSTIPATION and for bowel evacuation. (From Martindale, The Extra Pharmacopoeia, 30th ed, p871)	1.95	1	0	diarylmethane
bisindolylmaleimide i bisindolylmaleimide I: a bis(indolyl)maleimide	2.7	3	0
buformin Buformin: An oral hypoglycemic agent that inhibits gluconeogenesis, increases glycolysis, and decreases glucose oxidation.. buformin : A member of the class of biguanides that is biguanide substituted by a butyl group at position 1. It is an antidiabetic drug with potential antitumor effect.	1.95	1	0	biguanides	antineoplastic agent; antiviral agent; geroprotector; hypoglycemic agent; radiosensitizing agent
bumetanide [no description available]	5.28	17	0	amino acid; benzoic acids; sulfonamide	diuretic; EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor
buspirone Buspirone: An anxiolytic agent and serotonin receptor agonist belonging to the azaspirodecanedione class of compounds. Its structure is unrelated to those of the BENZODIAZAPINES, but it has an efficacy comparable to DIAZEPAM.. buspirone : An azaspiro compound that is 8-azaspiro[4.5]decane-7,9-dione substituted at the nitrogen atom by a 4-(piperazin-1-yl)butyl group which in turn is substituted by a pyrimidin-2-yl group at the N(4) position.	2.07	1	0	azaspiro compound; N-alkylpiperazine; N-arylpiperazine; organic heteropolycyclic compound; piperidones; pyrimidines	anxiolytic drug; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; sedative; serotonergic agonist
cacodylic acid dimethylarsinic acid : The organoarsenic compound that is arsenic acid substituted on the central arsenic atom with two methyl groups.	2.03	1	0	organoarsenic compound	xenobiotic metabolite
caffeine [no description available]	2.47	2	0	purine alkaloid; trimethylxanthine	adenosine A2A receptor antagonist; adenosine receptor antagonist; adjuvant; central nervous system stimulant; diuretic; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; environmental contaminant; food additive; fungal metabolite; geroprotector; human blood serum metabolite; mouse metabolite; mutagen; plant metabolite; psychotropic drug; ryanodine receptor agonist; xenobiotic
verapamil Verapamil: A calcium channel blocker that is a class IV anti-arrhythmia agent.. verapamil : A racemate comprising equimolar amounts of dexverapamil and (S)-verapamil. An L-type calcium channel blocker of the phenylalkylamine class, it is used (particularly as the hydrochloride salt) in the treatment of hypertension, angina pectoris and cardiac arrhythmia, and as a preventive medication for migraine.. 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile : A tertiary amino compound that is 3,4-dimethoxyphenylethylamine in which the hydrogens attached to the nitrogen are replaced by a methyl group and a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.	5.35	18	0	aromatic ether; nitrile; polyether; tertiary amino compound
camostat camostat : A benzoate ester resulting from the formal condensation of the carboxy group of 4-guanidinobenzoic acid with the hydroxy group of 2-(dimethylamino)-2-oxoethyl (4-hydroxyphenyl)acetate. It is a potent inhibitor of the human transmembrane protease serine 2 (TMPRSS2) and its mesylate salt is currently under investigation for its effectiveness in COVID-19 patients.	3.09	5	0	benzoate ester; carboxylic ester; diester; guanidines; tertiary carboxamide	anti-inflammatory agent; anticoronaviral agent; antifibrinolytic drug; antihypertensive agent; antineoplastic agent; antiviral agent; serine protease inhibitor
candesartan candesartan: a nonpeptide angiotensin II receptor antagonist. candesartan : A benzimidazolecarboxylic acid that is 1H-benzimidazole-7-carboxylic acid substituted by an ethoxy group at position 2 and a ({2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl}methyl) group at position 1. It is a angiotensin receptor antagonist used for the treatment of hypertension.	2.07	1	0	benzimidazolecarboxylic acid; biphenylyltetrazole	angiotensin receptor antagonist; antihypertensive agent; environmental contaminant; xenobiotic
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.	3.14	5	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
carmustine Carmustine: A cell-cycle phase nonspecific alkylating antineoplastic agent. It is used in the treatment of brain tumors and various other malignant neoplasms. (From Martindale, The Extra Pharmacopoeia, 30th ed, p462) This substance may reasonably be anticipated to be a carcinogen according to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985). (From Merck Index, 11th ed). carmustine : A member of the class of N-nitrosoureas that is 1,3-bis(2-chloroethyl)urea in which one of the nitrogens is substituted by a nitroso group.	1.97	1	0	N-nitrosoureas; organochlorine compound	alkylating agent; antineoplastic agent
carbonyl cyanide m-chlorophenyl hydrazone Carbonyl Cyanide m-Chlorophenyl Hydrazone: A proton ionophore. It is commonly used as an uncoupling agent and inhibitor of photosynthesis because of its effects on mitochondrial and chloroplast membranes.. CCCP : A member of the class of monochlorobenzenes that is benzene substituted by 2-(1,3-dinitrilopropan-2-ylidene)hydrazinyl and chloro groups at positions 1 and 3, respectively. It is a mitochondrial depolarizing agent that induces reactive oxygen species mediated cell death.	2.9	4	0	hydrazone; monochlorobenzenes; nitrile	antibacterial agent; geroprotector; ionophore
celecoxib [no description available]	4.28	5	0	organofluorine compound; pyrazoles; sulfonamide; toluenes	cyclooxygenase 2 inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug
cetirizine Cetirizine: A potent second-generation histamine H1 antagonist that is effective in the treatment of allergic rhinitis, chronic urticaria, and pollen-induced asthma. Unlike many traditional antihistamines, it does not cause drowsiness or anticholinergic side effects.. cetirizine : A member of the class of piperazines that is piperazine in which the hydrogens attached to nitrogen are replaced by a (4-chlorophenyl)(phenyl)methyl and a 2-(carboxymethoxy)ethyl group respectively.	3.57	2	0	ether; monocarboxylic acid; monochlorobenzenes; piperazines	anti-allergic agent; environmental contaminant; H1-receptor antagonist; xenobiotic
cetyltrimethylammonium ion Cetrimonium: Cetyltrimethylammonium compound whose salts and derivatives are used primarily as topical antiseptics.. cetyltrimethylammonium ion : A quaternary ammonium ion in which the substituents on nitrogen are one hexadecyl and three methyl groups.	1.96	1	0	quaternary ammonium ion
cetylpyridinium Cetylpyridinium: Cationic bactericidal surfactant used as a topical antiseptic for skin, wounds, mucous membranes, instruments, etc.; and also as a component in mouthwash and lozenges.	1.99	1	0	pyridinium ion
chelerythrine chelerythrine : A benzophenanthridine alkaloid isolated from the root of Zanthoxylum simulans, Chelidonium majus L., and other Papaveraceae.	2.48	2	0	benzophenanthridine alkaloid; organic cation	antibacterial agent; antineoplastic agent; EC 2.7.11.13 (protein kinase C) inhibitor
chlorambucil Chlorambucil: A nitrogen mustard alkylating agent used as antineoplastic for chronic lymphocytic leukemia, Hodgkin's disease, and others. Although it is less toxic than most other nitrogen mustards, it has been listed as a known carcinogen in the Fourth Annual Report on Carcinogens (NTP 85-002, 1985). (Merck Index, 11th ed). chlorambucil : A monocarboxylic acid that is butanoic acid substituted at position 4 by a 4-[bis(2-chloroethyl)amino]phenyl group. A chemotherapy drug that can be used in combination with the antibody obinutuzumab for the treatment of chronic lymphocytic leukemia.	2.39	2	0	aromatic amine; monocarboxylic acid; nitrogen mustard; organochlorine compound; tertiary amino compound	alkylating agent; antineoplastic agent; carcinogenic agent; drug allergen; immunosuppressive agent
chloroquine Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.	3.39	7	0	aminoquinoline; organochlorine compound; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; antirheumatic drug; autophagy inhibitor; dermatologic drug
chlorpromazine Chlorpromazine: The prototypical phenothiazine antipsychotic drug. Like the other drugs in this class chlorpromazine's antipsychotic actions are thought to be due to long-term adaptation by the brain to blocking DOPAMINE RECEPTORS. Chlorpromazine has several other actions and therapeutic uses, including as an antiemetic and in the treatment of intractable hiccup.. chlorpromazine : A substituted phenothiazine in which the ring nitrogen at position 10 is attached to C-3 of an N,N-dimethylpropanamine moiety.	4.18	17	0	organochlorine compound; phenothiazines; tertiary amine	anticoronaviral agent; antiemetic; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; phenothiazine antipsychotic drug
chlorpropamide Chlorpropamide: A sulfonylurea hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. (From Martindale, The Extra Pharmacopoeia, 30th ed, p277). chlorpropamide : An N-sulfonylurea that is urea in which a hydrogen attached to one of the nitrogens is substituted by 4-chlorobenzenesulfonyl group and a hydrogen attached to the other nitrogen is substituted by propyl group. Chlorpropamide is a hypoglycaemic agent used in the treatment of type 2 (non-insulin-dependent) diabetes mellitus not responding to dietary modification.	2	1	0	monochlorobenzenes; N-sulfonylurea	hypoglycemic agent; insulin secretagogue
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.	2.46	2	0	1,3-benzoxazoles; heteroaryl hydroxy compound; organochlorine compound	muscle relaxant; sedative
ciglitazone ciglitazone: structure given in second source; PPAR agonist used for type II diabetes. ciglitazone : An aromatic ether that consists of 1,3-thiazolidine-2,4-dione with position 5 substituted by a 4-[(1-methylcyclohexyl)methoxy]benzyl group. A selective PPARgamma agonist.	3.51	1	0	aromatic ether; thiazolidinone	antineoplastic agent; insulin-sensitizing drug
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.	5.88	32	0	aliphatic sulfide; guanidines; imidazoles; nitrile	adjuvant; analgesic; anti-ulcer drug; H2-receptor antagonist; P450 inhibitor
ciprofloxacin Ciprofloxacin: A broad-spectrum antimicrobial carboxyfluoroquinoline.. ciprofloxacin : A quinolone that is quinolin-4(1H)-one bearing cyclopropyl, carboxylic acid, fluoro and piperazin-1-yl substituents at positions 1, 3, 6 and 7, respectively.	4.64	8	0	aminoquinoline; cyclopropanes; fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone; zwitterion	antibacterial drug; antiinfective agent; antimicrobial agent; DNA synthesis inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; environmental contaminant; topoisomerase IV inhibitor; xenobiotic
cisapride Cisapride: A substituted benzamide used for its prokinetic properties. It is used in the management of gastroesophageal reflux disease, functional dyspepsia, and other disorders associated with impaired gastrointestinal motility. (Martindale The Extra Pharmacopoeia, 31st ed). cisapride : The amide resulting from formal condensation of 4-amino-5-chloro-2-methoxybenzoic acid with cis-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-amine. It has been used (as its monohydrate or as its tartrate) for the treatment of gastro-oesophageal reflux disease and for non-ulcer dyspepsia, but its propensity to cause cardiac arrhythmias resulted in its complete withdrawal from many countries, including the U.K., and restrictions on its use elsewhere.	2.06	1	0	benzamides
clofibrate angiokapsul: contains clofibrate & insoitolnicotinate	2.66	3	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.	1.99	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.	2.42	2	0	clonidine; imidazoline
clotrimazole [no description available]	2.46	2	0	conazole antifungal drug; imidazole antifungal drug; imidazoles; monochlorobenzenes	antiinfective agent; environmental contaminant; xenobiotic
conduritol epoxide conduritol epoxide: conduritol C epoxide refers to the (epi & neo)-isomers; structure. conduritol epoxide : An epoxide resulting from the epoxidation of the double bond of a conduritol.	3.06	5	0	cyclitol; epoxide; tetrol
cycloleucine Cycloleucine: An amino acid formed by cyclization of leucine. It has cytostatic, immunosuppressive and antineoplastic activities.. 1-aminocyclopentanecarboxylic acid : A non-proteinogenic alpha-amino acid that is cyclopentane substituted at position 1 by amino and carboxy groups.	1.96	1	0	non-proteinogenic alpha-amino acid	EC 2.5.1.6 (methionine adenosyltransferase) inhibitor
cypermethrin cypermethrin : A carboxylic ester resulting from the formal condensation between 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid and the alcoholic hydroxy group of hydroxy(3-phenoxyphenyl)acetonitrile.. zeta-cypermethrin : A diastereoisomeric mixture comprising the isomeric pair (1R)-cis-(alphaS)- and (1S)-trans-(alphaR)-cypermethrin together with the isomeric pair (1S)-cis-(alphaS)- and (1S)-trans-(alphaS)-cypermethrin where the ratio between the isomeric pairs lies in the range 45:55 to 55:45.	2.07	1	0	aromatic ether; cyclopropanecarboxylate ester; nitrile; organochlorine compound	agrochemical; molluscicide; pyrethroid ester acaricide; pyrethroid ester insecticide
dantrolene Dantrolene: Skeletal muscle relaxant that acts by interfering with excitation-contraction coupling in the muscle fiber. It is used in spasticity and other neuromuscular abnormalities. Although the mechanism of action is probably not central, dantrolene is usually grouped with the central muscle relaxants.. dantrolene : The hydrazone resulting from the formal condensation of 5-(4-nitrophenyl)furfural with 1-aminohydantoin. A ryanodine receptor antagonist used for the relief of chronic severe spasticity and malignant hyperthermia.	2.69	3	0	hydrazone; imidazolidine-2,4-dione	muscle relaxant; neuroprotective agent; ryanodine receptor antagonist
dapsone [no description available]	2.01	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.	1.96	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.	2.73	3	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.	2.91	4	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.	2.98	4	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.	2.06	1	0	1,4-benzodiazepinone; organochlorine compound	anticonvulsant; anxiolytic drug; GABA modulator; human metabolite; sedative
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.	2.92	4	0	1,4-benzodiazepinone; organochlorine compound	anticonvulsant; anxiolytic drug; environmental contaminant; sedative; xenobiotic
diazoxide Diazoxide: A benzothiadiazine derivative that is a peripheral vasodilator used for hypertensive emergencies. It lacks diuretic effect, apparently because it lacks a sulfonamide group.. diazoxide : A benzothiadiazine that is the S,S-dioxide of 2H-1,2,4-benzothiadiazine which is substituted at position 3 by a methyl group and at position 7 by chlorine. A peripheral vasodilator, it increases the concentration of glucose in the plasma and inhibits the secretion of insulin by the beta- cells of the pancreas. It is used orally in the management of intractable hypoglycaemia and intravenously in the management of hypertensive emergencies.	2.15	1	0	benzothiadiazine; organochlorine compound; sulfone	antihypertensive agent; beta-adrenergic agonist; bronchodilator agent; cardiotonic drug; diuretic; K-ATP channel agonist; sodium channel blocker; sympathomimetic agent; vasodilator agent
dibucaine Dibucaine: A local anesthetic of the amide type now generally used for surface anesthesia. It is one of the most potent and toxic of the long-acting local anesthetics and its parenteral use is restricted to spinal anesthesia. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1006). cinchocaine : A monocarboxylic acid amide that is the 2-(diethylamino)ethyl amide of 2-butoxyquinoline-4-carboxylic acid. One of the most potent and toxic of the long-acting local anesthetics, its parenteral use was restricted to spinal anesthesia. It is now generally only used (usually as the hydrochloride) in creams and ointments and in suppositories for temporary relief of pain and itching associated with skin and anorectal conditions.	2.36	2	0	aromatic ether; monocarboxylic acid amide; tertiary amino compound	topical anaesthetic
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.	4.62	8	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
pentetic acid Pentetic Acid: An iron chelating agent with properties like EDETIC ACID. DTPA has also been used as a chelator for other metals, such as plutonium.	1.98	1	0	pentacarboxylic acid	copper chelator
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.	1.99	1	0	monohydroxybenzoic acid; organofluorine compound	non-narcotic analgesic; non-steroidal anti-inflammatory drug
dimercaprol Dimercaprol: An anti-gas warfare agent that is effective against Lewisite (dichloro(2-chlorovinyl)arsine) and formerly known as British Anti-Lewisite or BAL. It acts as a chelating agent and is used in the treatment of arsenic, gold, and other heavy metal poisoning.. dimercaprol : A dithiol that is propane-1,2-dithiol in which one of the methyl hydrogens is replaced by a hydroxy group. a chelating agent originally developed during World War II as an experimental antidote against the arsenic-based poison gas Lewisite, it has been used clinically since 1949 for the treatment of poisoning by arsenic, mercury and gold. It can also be used for treatment of poisoning by antimony, bismuth and possibly thallium, and (with sodium calcium edetate) in cases of acute leaad poisoning. Administration is by (painful) intramuscular injection of a suspension of dimercaprol in peanut oil, typically every 4 hours for 2-10 days depending on the toxicity. In the past, dimercaprol was also used for the treatment of Wilson's disease, a severely debilitating genetic disorder in which the body tends to retain copper, with resultant liver and brain injury.	1.96	1	0	dithiol; primary alcohol	chelator
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.	2.36	2	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
dipyridamole Dipyridamole: A phosphodiesterase inhibitor that blocks uptake and metabolism of adenosine by erythrocytes and vascular endothelial cells. Dipyridamole also potentiates the antiaggregating action of prostacyclin. (From AMA Drug Evaluations Annual, 1994, p752). dipyridamole : A pyrimidopyrimidine that is 2,2',2'',2'''-(pyrimido[5,4-d]pyrimidine-2,6-diyldinitrilo)tetraethanol substituted by piperidin-1-yl groups at positions 4 and 8 respectively. A vasodilator agent, it inhibits the formation of blood clots.	3.29	6	0	piperidines; pyrimidopyrimidine; tertiary amino compound; tetrol	adenosine phosphodiesterase inhibitor; EC 3.5.4.4 (adenosine deaminase) inhibitor; platelet aggregation inhibitor; vasodilator agent
disopyramide Disopyramide: A class I anti-arrhythmic agent (one that interferes directly with the depolarization of the cardiac membrane and thus serves as a membrane-stabilizing agent) with a depressant action on the heart similar to that of guanidine. It also possesses some anticholinergic and local anesthetic properties.. disopyramide : A monocarboxylic acid amide that is butanamide substituted by a diisopropylamino group at position 4, a phenyl group at position 2 and a pyridin-2-yl group at position 2. It is used as a anti-arrhythmia drug.	3.81	3	0	monocarboxylic acid amide; pyridines; tertiary amino compound	anti-arrhythmia drug
disulfiram [no description available]	2.07	1	0	organic disulfide; organosulfur acaricide	angiogenesis inhibitor; antineoplastic agent; apoptosis inducer; EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor; EC 3.1.1.1 (carboxylesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 5.99.1.2 (DNA topoisomerase) inhibitor; ferroptosis inducer; fungicide; NF-kappaB inhibitor
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.	2.94	4	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
doxazosin Doxazosin: A prazosin-related compound that is a selective alpha-1-adrenergic blocker.. doxazosin : A member of the class of quinazolines that is quinazoline substituted by an amino group at position 4, methoxy groups at positions 6 and 7 and a piperazin-1-yl group at position 2 which in turn is substituted by a 2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl group at position 4. An antihypertensive agent, it is used in the treatment of high blood pressure.	2.07	1	0	aromatic amine; benzodioxine; monocarboxylic acid amide; N-acylpiperazine; N-arylpiperazine; quinazolines	alpha-adrenergic antagonist; antihyperplasia drug; antihypertensive agent; antineoplastic agent; vasodilator agent
ellipticine ellipticine : A organic heterotetracyclic compound that is pyrido[4,3-b]carbazole carrying two methyl substituents at positions 5 and 11.	2.07	1	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.	3.6	8	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.	4.15	16	0
ethacrynic acid Ethacrynic Acid: A compound that inhibits symport of sodium, potassium, and chloride primarily in the ascending limb of Henle, but also in the proximal and distal tubules. This pharmacological action results in excretion of these ions, increased urinary output, and reduction in extracellular fluid. This compound has been classified as a loop or high ceiling diuretic.. etacrynic acid : An aromatic ether that is phenoxyacetic acid in which the phenyl ring is substituted by chlorines at positions 2 and 3, and by a 2-methylidenebutanoyl group at position 4. It is a loop diuretic used to treat high blood pressure resulting from diseases such as congestive heart failure, liver failure, and kidney failure. It is also a glutathione S-transferase (EC 2.5.1.18) inhibitor.	2.65	3	0	aromatic ether; aromatic ketone; dichlorobenzene; monocarboxylic acid	EC 2.5.1.18 (glutathione transferase) inhibitor; ion transport inhibitor; loop diuretic
ether Ether: A mobile, very volatile, highly flammable liquid used as an inhalation anesthetic and as a solvent for waxes, fats, oils, perfumes, alkaloids, and gums. It is mildly irritating to skin and mucous membranes.. ether : An organooxygen compound with formula ROR, where R is not hydrogen.. diethyl ether : An ether in which the oxygen atom is linked to two ethyl groups.	1.94	1	0	ether; volatile organic compound	inhalation anaesthetic; non-polar solvent; refrigerant
famotidine Famotidine: A competitive histamine H2-receptor antagonist. Its main pharmacodynamic effect is the inhibition of gastric secretion.	1.99	1	0	1,3-thiazoles; guanidines; sulfonamide	anti-ulcer drug; H2-receptor antagonist; P450 inhibitor
carbonyl cyanide p-trifluoromethoxyphenylhydrazone Carbonyl Cyanide p-Trifluoromethoxyphenylhydrazone: A proton ionophore that is commonly used as an uncoupling agent in biochemical studies.. carbonyl cyanide p-trifluoromethoxyphenylhydrazone : A hydrazone that is hydrazonomalononitrile in which one of the hydrazine hydrogens is substituted by a p-trifluoromethoxyphenyl group.	2.38	2	0	aromatic ether; hydrazone; nitrile; organofluorine compound	ATP synthase inhibitor; geroprotector; ionophore
felodipine Felodipine: A dihydropyridine calcium antagonist with positive inotropic effects. It lowers blood pressure by reducing peripheral vascular resistance through a highly selective action on smooth muscle in arteriolar resistance vessels.. felodipine : The mixed (methyl, ethyl) diester of 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid. A calcium-channel blocker, it lowers blood pressure by reducing peripheral vascular resistance through a highly selective action on smooth muscle in arteriolar resistance vessels. It is used in the management of hypertension and angina pectoris.	3	4	0	dichlorobenzene; dihydropyridine; ethyl ester; methyl ester	anti-arrhythmia drug; antihypertensive agent; calcium channel blocker; vasodilator agent
fendiline Fendiline: Coronary vasodilator; inhibits calcium function in muscle cells in excitation-contraction coupling; proposed as antiarrhythmic and antianginal agents.	2.46	2	0	diarylmethane
fenofibrate Pharmavit: a polyvitamin product, comprising vitamins A, D2, B1, B2, B6, C, E, nicotinamide, & calcium pantothene; may be a promising agent for application to human populations exposed to carcinogenic and genetic hazards of ionizing radiation; RN from CHEMLINE	2.76	3	0	aromatic ether; chlorobenzophenone; isopropyl ester; monochlorobenzenes	antilipemic drug; environmental contaminant; geroprotector; xenobiotic
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.	2.06	1	0	monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; non-narcotic analgesic; non-steroidal anti-inflammatory drug
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.	2.07	1	0	anilide; monocarboxylic acid amide; piperidines	adjuvant; anaesthesia adjuvant; anaesthetic; intravenous anaesthetic; mu-opioid receptor agonist; opioid analgesic
fexofenadine fexofenadine: a second generation antihistamine; metabolite of the antihistaminic drug terfenadine; structure in first source; RN refers to HCl. fexofenadine : A piperidine-based anti-histamine compound.	4.65	8	0	piperidines; tertiary amine	anti-allergic agent; H1-receptor antagonist
fleroxacin Fleroxacin: A broad-spectrum antimicrobial fluoroquinolone. The drug strongly inhibits the DNA-supercoiling activity of DNA GYRASE.. fleroxacin : A fluoroquinolone antibiotic that is 4-oxo-1,4-dihydroquinoline which is substituted at positions 1, 3, 6, 7 and 8 by 2-fluoroethyl, carboxy, fluoro, 4-methylpiperazin-1-yl and fluoro groups, respectively. It is active against many Gram-positive and Gram-negative bacteria.	2.06	1	0	difluorobenzene; fluoroquinolone antibiotic; monocarboxylic acid; N-alkylpiperazine; quinolines	antibacterial drug; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; topoisomerase IV inhibitor
fluconazole Fluconazole: Triazole antifungal agent that is used to treat oropharyngeal CANDIDIASIS and cryptococcal MENINGITIS in AIDS.. fluconazole : A member of the class of triazoles that is propan-2-ol substituted at position 1 and 3 by 1H-1,2,4-triazol-1-yl groups and at position 2 by a 2,4-difluorophenyl group. It is an antifungal drug used for the treatment of mucosal candidiasis and for systemic infections including systemic candidiasis, coccidioidomycosis, and cryptococcosis.	2.47	2	0	conazole antifungal drug; difluorobenzene; tertiary alcohol; triazole antifungal drug	environmental contaminant; P450 inhibitor; xenobiotic
flufenamic acid Flufenamic Acid: An anthranilic acid derivative with analgesic, anti-inflammatory, and antipyretic properties. It is used in musculoskeletal and joint disorders and administered by mouth and topically. (From Martindale, The Extra Pharmacopoeia, 30th ed, p16). flufenamic acid : An aromatic amino acid consisting of anthranilic acid carrying an N-(trifluoromethyl)phenyl substituent. An analgesic and anti-inflammatory, it is used in rheumatic disorders.	1.95	1	0	aromatic amino acid; organofluorine compound	antipyretic; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
flumazenil Flumazenil: A potent benzodiazepine receptor antagonist. Since it reverses the sedative and other actions of benzodiazepines, it has been suggested as an antidote to benzodiazepine overdoses.. flumazenil : An organic heterotricyclic compound that is 5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine which is substituted at positions 3, 5, 6, and 8 by ethoxycarbonyl, methyl, oxo, and fluoro groups, respectively. It is used as an antidote to benzodiazepine overdose.	2.06	1	0	ethyl ester; imidazobenzodiazepine; organofluorine compound	antidote to benzodiazepine poisoning; GABA antagonist
fluorescite fluorescein (acid form) : A xanthene dye that is highly fluorescent and commonly used as a fluorescent tracer.	2.04	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.	2.71	3	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.	2.07	1	0	(trifluoromethyl)benzenes; aromatic ether; secondary amino compound
flurbiprofen Flurbiprofen: An anti-inflammatory analgesic and antipyretic of the phenylalkynoic acid series. It has been shown to reduce bone resorption in periodontal disease by inhibiting CARBONIC ANHYDRASE.. flurbiprofen : A monocarboxylic acid that is a 2-fluoro-[1,1'-biphenyl-4-yl] moiety linked to C-2 of propionic acid. A non-steroidal anti-inflammatory, analgesic and antipyretic, it is used as a pre-operative anti-miotic as well as orally for arthritis or dental pain.	2.46	2	0	fluorobiphenyl; monocarboxylic acid	antipyretic; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
flutamide Flutamide: An antiandrogen with about the same potency as cyproterone in rodent and canine species.	2.74	3	0	(trifluoromethyl)benzenes; monocarboxylic acid amide	androgen antagonist; antineoplastic agent
furafylline [no description available]	2.07	1	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.	6.09	15	0	chlorobenzoic acid; furans; sulfonamide	environmental contaminant; loop diuretic; xenobiotic
fusaric acid Fusaric Acid: A picolinic acid derivative isolated from various Fusarium species. It has been proposed for a variety of therapeutic applications but is primarily used as a research tool. Its mechanisms of action are poorly understood. It probably inhibits DOPAMINE BETA-HYDROXYLASE, the enzyme that converts dopamine to norepinephrine. It may also have other actions, including the inhibition of cell proliferation and DNA synthesis.	2.04	1	0	aromatic carboxylic acid; pyridines
gabapentin Gabapentin: A cyclohexane-gamma-aminobutyric acid derivative that is used for the treatment of PARTIAL SEIZURES; NEURALGIA; and RESTLESS LEGS SYNDROME.. gabapentin : A gamma-amino acid that is cyclohexane substituted at position 1 by aminomethyl and carboxymethyl groups. Used for treatment of neuropathic pain and restless legs syndrome.	2.06	1	0	gamma-amino acid	anticonvulsant; calcium channel blocker; environmental contaminant; xenobiotic
gabexate Gabexate: A serine proteinase inhibitor used therapeutically in the treatment of pancreatitis, disseminated intravascular coagulation (DIC), and as a regional anticoagulant for hemodialysis. The drug inhibits the hydrolytic effects of thrombin, plasmin, and kallikrein, but not of chymotrypsin and aprotinin.	3.61	9	0	benzoate ester
gemfibrozil [no description available]	2.95	4	0	aromatic ether	antilipemic drug
gentamicin Gentamicins: A complex of closely related aminoglycosides obtained from MICROMONOSPORA purpurea and related species. They are broad-spectrum antibiotics, but may cause ear and kidney damage. They act to inhibit PROTEIN BIOSYNTHESIS.	2.92	4	0
gliclazide Gliclazide: An oral sulfonylurea hypoglycemic agent which stimulates insulin secretion.	2.79	3	0	N-sulfonylurea	hypoglycemic agent; insulin secretagogue; radical scavenger
glimepiride glimepiride: structure given in first source	2.04	1	0	sulfonamide
glipizide Glipizide: An oral hypoglycemic agent which is rapidly absorbed and completely metabolized.. glipizide : An N-sulfonylurea that is glyburide in which the (5-chloro-2-methoxybenzoyl group is replaced by a (5-methylpyrazin-2-yl)carbonyl group. An oral hypoglycemic agent, it is used in the treatment of type 2 diabetes mellitus.	2.75	3	0	aromatic amide; monocarboxylic acid amide; N-sulfonylurea; pyrazines	EC 2.7.1.33 (pantothenate kinase) inhibitor; hypoglycemic agent; insulin secretagogue
glutaral Glutaral: One of the protein CROSS-LINKING REAGENTS that is used as a disinfectant for sterilization of heat-sensitive equipment and as a laboratory reagent, especially as a fixative.. glutaraldehyde : A dialdehyde comprised of pentane with aldehyde functions at C-1 and C-5.	2.43	2	0	dialdehyde	cross-linking reagent; disinfectant; fixative
glyburide Glyburide: An antidiabetic sulfonylurea derivative with actions like those of chlorpropamide. glyburide : An N-sulfonylurea that is acetohexamide in which the acetyl group is replaced by a 2-(5-chloro-2-methoxybenzamido)ethyl group.	4.91	11	0	monochlorobenzenes; N-sulfonylurea	anti-arrhythmia drug; EC 2.7.1.33 (pantothenate kinase) inhibitor; EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor; hypoglycemic agent
go 6976 [no description available]	2.44	2	0	indolocarbazole; organic heterohexacyclic compound	EC 2.7.11.13 (protein kinase C) inhibitor
guaiazulene guaiazulene: structure	1.99	1	0	sesquiterpene
guaifenesin Guaifenesin: An expectorant that also has some muscle relaxing action. It is used in many cough preparations.	4.78	10	0	methoxybenzenes
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	1	0	carboxamidine; guanidines; one-carbon compound
haloperidol Haloperidol: A phenyl-piperidinyl-butyrophenone that is used primarily to treat SCHIZOPHRENIA and other PSYCHOSES. It is also used in schizoaffective disorder, DELUSIONAL DISORDERS, ballism, and TOURETTE SYNDROME (a drug of choice) and occasionally as adjunctive therapy in INTELLECTUAL DISABILITY and the chorea of HUNTINGTON DISEASE. It is a potent antiemetic and is used in the treatment of intractable HICCUPS. (From AMA Drug Evaluations Annual, 1994, p279). haloperidol : A compound composed of a central piperidine structure with hydroxy and p-chlorophenyl substituents at position 4 and an N-linked p-fluorobutyrophenone moiety.	2.46	2	0	aromatic ketone; hydroxypiperidine; monochlorobenzenes; organofluorine compound; tertiary alcohol	antidyskinesia agent; antiemetic; dopaminergic antagonist; first generation antipsychotic; serotonergic antagonist
hexafluorenium hexafluorenium: curarimimetic agent for use with succinylcholine; muscle relaxant; structure; RN given refers to parent cpd	1.96	1	0	quaternary ammonium salt
hydralazine Hydralazine: A direct-acting vasodilator that is used as an antihypertensive agent.. hydralazine : The 1-hydrazino derivative of phthalazine; a direct-acting vasodilator that is used as an antihypertensive agent.	2.03	1	0	azaarene; hydrazines; ortho-fused heteroarene; phthalazines	antihypertensive agent; vasodilator agent
hydrochlorothiazide Hydrochlorothiazide: A thiazide diuretic often considered the prototypical member of this class. It reduces the reabsorption of electrolytes from the renal tubules. This results in increased excretion of water and electrolytes, including sodium, potassium, chloride, and magnesium. It is used in the treatment of several disorders including edema, hypertension, diabetes insipidus, and hypoparathyroidism.. hydrochlorothiazide : A benzothiadiazine that is 3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide substituted by a chloro group at position 6 and a sulfonamide at 7. It is diuretic used for the treatment of hypertension and congestive heart failure.	2.46	2	0	benzothiadiazine; organochlorine compound; sulfonamide	antihypertensive agent; diuretic; environmental contaminant; xenobiotic
hydroxyurea [no description available]	1.99	1	0	one-carbon compound; ureas	antimetabolite; antimitotic; antineoplastic agent; DNA synthesis inhibitor; EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor; genotoxin; immunomodulator; radical scavenger; teratogenic agent
ibuprofen Midol: combination of cinnamedrine, phenacetin, aspirin & caffeine	3.41	7	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
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.	3.78	11	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.	2.91	4	0	dibenzoazepine	adrenergic uptake inhibitor; antidepressant; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
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.	5.41	61	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
iodoacetamide [no description available]	2.38	2	0
iohexol Iohexol: An effective non-ionic, water-soluble contrast agent which is used in myelography, arthrography, nephroangiography, arteriography, and other radiographic procedures. Its low systemic toxicity is the combined result of low chemotoxicity and low osmolality.. iohexol : A benzenedicarboxamide compound having N-(2,3-dihydroxypropyl)carbamoyl groups at the 1- and 3-positions, iodo substituents at the 2-, 4- and 6-positions and an N-(2,3-dihydroxypropyl)acetamido group at the 5-position.	2.91	4	0	benzenedicarboxamide; organoiodine compound	environmental contaminant; radioopaque medium; xenobiotic
iopanoic acid Iopanoic Acid: Radiopaque medium used as diagnostic aid.	3.35	7	0	monocarboxylic acid
iopromide iopromide: structure given in first source. iopromide : A dicarboxylic acid diamide that consists of N-methylisophthalamide bearing three iodo substituents at positions 2, 4 and 6, a methoxyacetyl substituent at position 5 and two 2,3-dihydroxypropyl groups attached to the amide nitrogens. A water soluble x-ray contrast agent for intravascular administration.	2.41	2	0	dicarboxylic acid diamide; organoiodine compound	environmental contaminant; nephrotoxic agent; radioopaque medium; xenobiotic
iodipamide Iodipamide: A water-soluble radiographic contrast media for cholecystography and intravenous cholangiography.. adipiodone : An organoiodine compound that is 3-amino-2,4,6-triiodobenzoic acid in which one of the amino hydrogens is substituted by a 6-(3-carboxy-2,4,6-triiodoanilino)-6-oxohexanoyl group. It is a water-soluble radiographic contrast media for cholecystography and intravenous cholangiography.	3.05	5	0	benzoic acids; organoiodine compound; secondary carboxamide	radioopaque medium
avapro Irbesartan: A spiro compound, biphenyl and tetrazole derivative that acts as an angiotensin II type 1 receptor antagonist. It is used in the management of HYPERTENSION, and in the treatment of kidney disease.. irbesartan : A biphenylyltetrazole that is an angiotensin II receptor antagonist used mainly for the treatment of hypertension.	3.51	1	0	azaspiro compound; biphenylyltetrazole	angiotensin receptor antagonist; antihypertensive agent; environmental contaminant; xenobiotic
1-methyl-3-isobutylxanthine 1-Methyl-3-isobutylxanthine: A potent cyclic nucleotide phosphodiesterase inhibitor; due to this action, the compound increases cyclic AMP and cyclic GMP in tissue and thereby activates CYCLIC NUCLEOTIDE-REGULATED PROTEIN KINASES. 3-isobutyl-1-methylxanthine : An oxopurine that is xanthine which is substituted at positions 1 and 3 by methyl and isobutyl groups, respectively.	2.67	3	0	3-isobutyl-1-methylxanthine
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).	7.91	4	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.	3.08	5	0	catechols; secondary alcohol; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; cardiotonic drug; sympathomimetic agent
isradipine Isradipine: A potent antagonist of CALCIUM CHANNELS that is highly selective for VASCULAR SMOOTH MUSCLE. It is effective in the treatment of chronic stable angina pectoris, hypertension, and congestive cardiac failure.	2.46	2	0	benzoxadiazole; dihydropyridine; isopropyl ester; methyl ester
itraconazole [no description available]	2.07	1	0	piperazines
ketanserin Ketanserin: A selective serotonin receptor antagonist with weak adrenergic receptor blocking properties. The drug is effective in lowering blood pressure in essential hypertension. It also inhibits platelet aggregation. It is well tolerated and is particularly effective in older patients.. ketanserin : A member of the class of quinazolines that is quinazoline-2,4(1H,3H)-dione which is substituted at position 3 by a 2-[4-(p-fluorobenzoyl)piperidin-1-yl]ethyl group.	1.99	1	0	aromatic ketone; organofluorine compound; piperidines; quinazolines	alpha-adrenergic antagonist; antihypertensive agent; cardiovascular drug; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; serotonergic antagonist
ketoconazole 1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine : A dioxolane that is 1,3-dioxolane which is substituted at positions 2, 2, and 4 by imidazol-1-ylmethyl, 2,4-dichlorophenyl, and [para-(4-acetylpiperazin-1-yl)phenoxy]methyl groups, respectively.	3.61	9	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.	3.14	5	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
ketorolac Ketorolac: A pyrrolizine carboxylic acid derivative structurally related to INDOMETHACIN. It is an NSAID and is used principally for its analgesic activity. (From Martindale The Extra Pharmacopoeia, 31st ed). ketorolac : A racemate comprising equimolar amounts of (R)-(+)- and (S)-(-)-5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid. While only the (S)-(-) enantiomer is a COX1 and COX2 inhibitor, the (R)-(+) enantiomer exhibits potent analgesic activity. A non-steroidal anti-inflammatory drug, ketorolac is mainly used (generally as the tromethamine salt) for its potent analgesic properties in the short-term management of post-operative pain, and in eye drops to relieve the ocular itching associated with seasonal allergic conjunctivitis. It was withdrawn from the market in many countries in 1993 following association with haemorrhage and renal failure.. 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid : A member of the class of pyrrolizines that is 2,3-dihydro-1H-pyrrolizine which is substituted at positions 1 and 5 by carboxy and benzoyl groups, respectively.	2.06	1	0	amino acid; aromatic ketone; monocarboxylic acid; pyrrolizines; racemate	analgesic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; non-steroidal anti-inflammatory drug
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.	2.06	1	0	benzamides; benzenes; phenols; primary carboxamide; salicylamides; secondary alcohol; secondary amino compound
lamotrigine [no description available]	2.07	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.	2.94	4	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.	2	1	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.	2.05	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
loperamide Loperamide: One of the long-acting synthetic ANTIDIARRHEALS; it is not significantly absorbed from the gut, and has no effect on the adrenergic system or central nervous system, but may antagonize histamine and interfere with acetylcholine release locally.. loperamide : A synthetic piperidine derivative, effective against diarrhoea resulting from gastroenteritis or inflammatory bowel disease.	4.04	4	0	monocarboxylic acid amide; monochlorobenzenes; piperidines; tertiary alcohol	anticoronaviral agent; antidiarrhoeal drug; mu-opioid receptor agonist
loratadine Loratadine: A second-generation histamine H1 receptor antagonist used in the treatment of allergic rhinitis and urticaria. Unlike most classical antihistamines (HISTAMINE H1 ANTAGONISTS) it lacks central nervous system depressing effects such as drowsiness.. loratadine : A benzocycloheptapyridine that is 6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine substituted by a chloro group at position 8 and a 1-(ethoxycarbonyl)piperidin-4-ylidene group at position 11. It is a H1-receptor antagonist commonly employed in the treatment of allergic disorders.	2.46	2	0	benzocycloheptapyridine; ethyl ester; N-acylpiperidine; organochlorine compound; tertiary carboxamide	anti-allergic agent; cholinergic antagonist; geroprotector; H1-receptor antagonist
lorglumide lorglumide: RN given refers to (+-)-isomer. lorglumide : A racemate comprising equal amounts of (R)- and (S)-lorglumide.. N(2)-(3,4-dichlorobenzoyl)-N,N-dipentyl-alpha-glutamine : A dicarboxylic acid monoamide obtained by formal condensation of the alpha-carboxy group of N-(3,4-dichlorobenzoyl)glutamic acid with the amino group of dipentylamine.	1.97	1	0	benzamides; dicarboxylic acid monoamide; dichlorobenzene; glutamic acid derivative
loxoprofen loxoprofen: RN given refers to parent cpd without isomeric designation; structure in first source. loxoprofen : A monocarboxylic acid that is propionic acid in which one of the hydrogens at position 2 is substituted by a 4-[(2-oxocyclopentyl)methyl]phenyl group. A prodrug that is rapidly converted into its active trans-alcohol metabolite following oral administration.	2.06	1	0	cyclopentanones; monocarboxylic acid	antipyretic; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; prodrug
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	2.72	3	0	chromones; morpholines; organochlorine compound	autophagy inhibitor; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor; geroprotector
maprotiline Maprotiline: A bridged-ring tetracyclic antidepressant that is both mechanistically and functionally similar to the tricyclic antidepressants, including side effects associated with its use.	2.04	1	0	anthracenes
mefenamic acid Mefenamic Acid: A non-steroidal anti-inflammatory agent with analgesic, anti-inflammatory, and antipyretic properties. It is an inhibitor of cyclooxygenase.. mefenamic acid : An aminobenzoic acid that is anthranilic acid in which one of the hydrogens attached to the nitrogen is replaced by a 2,3-dimethylphenyl group. Although classed as a non-steroidal anti-inflammatory drug, its anti-inflammatory properties are considered to be minor. It is used to relieve mild to moderate pain, including headaches, dental pain, osteoarthritis and rheumatoid arthritis.	2.66	3	0	aminobenzoic acid; secondary amino compound	analgesic; antipyretic; antirheumatic drug; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-steroidal anti-inflammatory drug; xenobiotic
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.	2.07	1	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.	2.04	1	0	amino acid; aromatic amine; monocarboxylic acid; monohydroxybenzoic acid; phenols	non-steroidal anti-inflammatory drug
metformin Metformin: A biguanide hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. Metformin improves glycemic control by improving insulin sensitivity and decreasing intestinal absorption of glucose. (From Martindale, The Extra Pharmacopoeia, 30th ed, p289). metformin : A member of the class of guanidines that is biguanide the carrying two methyl substituents at position 1.	3.57	2	0	guanidines	environmental contaminant; geroprotector; hypoglycemic agent; xenobiotic
methiothepin Methiothepin: A serotonin receptor antagonist in the CENTRAL NERVOUS SYSTEM used as an antipsychotic.. methiothepin : A dibenzothiepine that is 10,11-dihydrodibenzo[b,f]thiepine bearing additional methylthio and 4-methylpiperazin-1-yl substituents at positions 8 and 10 respectively. Potent 5-HT2 antagonist, also active as 5-HT1 antagonist. Differentiates 5-HT1D sub-types. Also displays affinity for rodent 5-HT5B, 5-HT5A, 5-HT7 and 5-HT6 receptors (pK1 values are 6.6, 7.0, 8.4 and 8.7 respectively).	1.99	1	0	aryl sulfide; dibenzothiepine; N-alkylpiperazine; tertiary amino compound	antipsychotic agent; dopaminergic antagonist; geroprotector; serotonergic antagonist
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.	2.07	1	0	aromatic ether; psoralens	antineoplastic agent; cross-linking reagent; dermatologic drug; photosensitizing agent; plant metabolite
nocodazole [no description available]	2	1	0	aromatic ketone; benzimidazoles; carbamate ester; thiophenes	antimitotic; antineoplastic agent; microtubule-destabilising agent; tubulin modulator
metolazone Metolazone: A quinazoline-sulfonamide derived DIURETIC that functions by inhibiting SODIUM CHLORIDE SYMPORTERS.. metolazone : A quinazoline that consists of 1,2,3,4-tetrahydroquinazolin-4-one bearing additional methyl, 2-tolyl, sulfamyl and chloro substituents at positions 2, 3, 6 and 7 respectively. A quinazoline diuretic, with properties similar to thiazide diuretics.	2.06	1	0	organochlorine compound; quinazolines; sulfonamide	antihypertensive agent; diuretic; ion transport inhibitor
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.	3.13	5	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.	3.25	6	0	C-nitro compound; imidazoles; primary alcohol	antiamoebic agent; antibacterial drug; antimicrobial agent; antiparasitic agent; antitrichomonal drug; environmental contaminant; prodrug; radiosensitizing agent; xenobiotic
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.	2.07	1	0	imidazobenzodiazepine; monofluorobenzenes; organochlorine compound	anticonvulsant; antineoplastic agent; anxiolytic drug; apoptosis inducer; central nervous system depressant; GABAA receptor agonist; general anaesthetic; muscle relaxant; sedative
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.	4.25	5	0	dihydroxyanthraquinone	analgesic; antineoplastic agent
moclobemide Moclobemide: A reversible inhibitor of monoamine oxidase type A; (RIMA); (see MONOAMINE OXIDASE INHIBITORS) that has antidepressive properties.. moclobemide : A member of the class of benzamides that is benzamide substituted by a chloro group at position 4 and a 2-(morpholin-4-yl)ethyl group at the nitrogen atom. It acts as a reversible monoamine oxidase inhibitor and is used in the treatment of depression.	2.07	1	0	benzamides; monochlorobenzenes; morpholines	antidepressant; environmental contaminant; xenobiotic
acecainide Acecainide: A major metabolite of PROCAINAMIDE. Its anti-arrhythmic action may cause cardiac toxicity in kidney failure.. N-acetylprocainamide : A benzamide obtained via formal condensation of 4-acetamidobenzoic acid and 2-(diethylamino)ethylamine.	1.97	1	0	acetamides; benzamides	anti-arrhythmia drug
ethylmaleimide Ethylmaleimide: A sulfhydryl reagent that is widely used in experimental biochemical studies.	3.57	9	0	maleimides	anticoronaviral agent; EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor; EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor; EC 2.7.1.1 (hexokinase) inhibitor
fenamic acid fenamic acid: has chloride and potassium channel-blocking activity; RN given refers to parent cpd. fenamic acid : An aminobenzoic acid that is the N-phenyl derivative of anthranilic acid. It acts as a parent skeleton for the synthesis of several non-steroidal anti-inflammatory drugs.	2	1	0	aminobenzoic acid; secondary amino compound	membrane transport modulator
nafamostat nafamostat: inhibitor of trypsin, plasmin, pancreatic kallikrein, plasma kallikrein & thrombin; strongly inhibits esterolytic activities of C1r & C1 esterase complement-mediated hemolysis; antineoplastic	3.08	5	0	benzoic acids; guanidines
nalidixic acid [no description available]	2.42	2	0	1,8-naphthyridine derivative; monocarboxylic acid; quinolone antibiotic	antibacterial drug; antimicrobial agent; DNA synthesis inhibitor
nefazodone nefazodone: may be useful as an opiate adjunct	2.07	1	0	aromatic ether; monochlorobenzenes; N-alkylpiperazine; N-arylpiperazine; triazoles	alpha-adrenergic antagonist; analgesic; antidepressant; serotonergic antagonist; serotonin uptake inhibitor
neostigmine Neostigmine: A cholinesterase inhibitor used in the treatment of myasthenia gravis and to reverse the effects of muscle relaxants such as gallamine and tubocurarine. Neostigmine, unlike PHYSOSTIGMINE, does not cross the blood-brain barrier.. neostigmine : A quaternary ammonium ion comprising an anilinium ion core having three methyl substituents on the aniline nitrogen, and a 3-[(dimethylcarbamoyl)oxy] substituent at position 3. It is a parasympathomimetic which acts as a reversible acetylcholinesterase inhibitor.	2.35	2	0	quaternary ammonium ion	antidote to curare poisoning; EC 3.1.1.7 (acetylcholinesterase) 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.	2.73	3	0	cyclopropanes; dipyridodiazepine	antiviral drug; HIV-1 reverse transcriptase inhibitor
nicardipine Nicardipine: A potent calcium channel blockader with marked vasodilator action. It has antihypertensive properties and is effective in the treatment of angina and coronary spasms without showing cardiodepressant effects. It has also been used in the treatment of asthma and enhances the action of specific antineoplastic agents.. nicardipine : A racemate comprising equimolar amounts of (R)- and (S)-nicardipine. It is a calcium channel blocker which is used to treat hypertension.. 2-[benzyl(methyl)amino]ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate : A dihydropyridine that is 1,4-dihydropyridine substituted by a methyl, {2-[benzyl(methyl)amino]ethoxy}carbonyl, 3-nitrophenyl, methoxycarbonyl and methyl groups at positions 2, 3, 4, 5 and 6, respectively.	2.46	2	0	benzenes; C-nitro compound; diester; dihydropyridine; methyl ester; tertiary amino compound
nifedipine Nifedipine: A potent vasodilator agent with calcium antagonistic action. It is a useful anti-anginal agent that also lowers blood pressure.	3.13	5	0	C-nitro compound; dihydropyridine; methyl ester	calcium channel blocker; human metabolite; tocolytic agent; vasodilator agent
nimesulide nimesulide: structure. nimesulide : An aromatic ether having phenyl and 2-methylsulfonamido-5-nitrophenyl as the two aryl groups.	1.99	1	0	aromatic ether; C-nitro compound; sulfonamide	cyclooxygenase 2 inhibitor; non-steroidal anti-inflammatory drug
nimodipine Nimodipine: A calcium channel blockader with preferential cerebrovascular activity. It has marked cerebrovascular dilating effects and lowers blood pressure.. nimodipine : A dihydropyridine that is 1,4-dihydropyridine which is substituted by methyl groups at positions 2 and 6, a (2-methoxyethoxy)carbonyl group at position 3, a m-nitrophenyl group at position 4, and an isopropoxycarbonyl group at position 5. An L-type calcium channel blocker, it acts particularly on cerebral circulation, and is used both orally and intravenously for the prevention and treatment of subarachnoid hemorrhage from ruptured intracranial aneurysm.	2.17	1	0	2-methoxyethyl ester; C-nitro compound; dicarboxylic acids and O-substituted derivatives; diester; dihydropyridine; isopropyl ester	antihypertensive agent; calcium channel blocker; cardiovascular drug; vasodilator agent
nisoldipine Nisoldipine: A dihydropyridine calcium channel antagonist that acts as a potent arterial vasodilator and antihypertensive agent. It is also effective in patients with cardiac failure and angina.. nisoldipine : A racemate consisting of equimolar amounts of (R)- and (S)-nisoldipine. A calcium channel blocker, it is used in the treatment of hypertension and angina pectoris.. methyl 2-methylpropyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate : A dihydropyridine that is 1,4-dihydropyridine which is substituted by methyl groups at positions 2 and 6, a methoxycarbonyl group at position 3, an o-nitrophenyl group at position 4, and an isobutoxycarbonyl group at position 5. The racemate, a calcium channel blocker, is used in the treatment of hypertension and angina pectoris.	1.99	1	0	C-nitro compound; dicarboxylic acids and O-substituted derivatives; diester; dihydropyridine; methyl ester
nitrendipine Nitrendipine: A calcium channel blocker with marked vasodilator action. It is an effective antihypertensive agent and differs from other calcium channel blockers in that it does not reduce glomerular filtration rate and is mildly natriuretic, rather than sodium retentive.. nitrendipine : A dihydropyridine that is 1,4-dihydropyridine substituted by methyl groups at positions 2 and 6, a 3-nitrophenyl group at position 4, a ethoxycarbonyl group at position 3 and a methoxycarbonyl group at position 5. It is a calcium-channel blocker used in the treatment of hypertension.	2.46	2	0	C-nitro compound; dicarboxylic acids and O-substituted derivatives; diester; dihydropyridine; ethyl ester; methyl ester	antihypertensive agent; calcium channel blocker; geroprotector; vasodilator agent
nizatidine [no description available]	2.04	1	0	1,3-thiazoles; C-nitro compound; carboxamidine; organic sulfide; tertiary amino compound	anti-ulcer drug; cholinergic drug; H2-receptor antagonist
n-(2-cyclohexyloxy-4-nitrophenyl)methanesulfonamide N-(2-cyclohexyloxy-4-nitrophenyl)methanesulfonamide: structure given in first source. NS-398 : A C-nitro compound that is N-methylsulfonyl-4-nitroaniline bearing an additional cyclohexyloxy substituent at position 2.	2.69	3	0	aromatic ether; C-nitro compound; sulfonamide	antineoplastic agent; cyclooxygenase 2 inhibitor
ofloxacin Ofloxacin: A synthetic fluoroquinolone antibacterial agent that inhibits the supercoiling activity of bacterial DNA GYRASE, halting DNA REPLICATION.. 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid : An oxazinoquinoline that is 2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinolin-7-one substituted by methyl, carboxy, fluoro, and 4-methylpiperazin-1-yl groups at positions 3, 6, 9, and 10, respectively.. ofloxacin : A racemate comprising equimolar amounts of levofloxacin and dextrofloxacin. It is a synthetic fluoroquinolone antibacterial agent which inhibits the supercoiling activity of bacterial DNA gyrase, halting DNA replication.	2.72	3	0	3-oxo monocarboxylic acid; N-arylpiperazine; N-methylpiperazine; organofluorine compound; oxazinoquinoline
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.	3.5	8	0	aromatic ether; benzimidazoles; pyridines; sulfoxide
ondansetron Ondansetron: A competitive serotonin type 3 receptor antagonist. It is effective in the treatment of nausea and vomiting caused by cytotoxic chemotherapy drugs, including cisplatin, and has reported anxiolytic and neuroleptic properties.	2.47	2	0	carbazoles
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.	2.46	2	0	1,4-benzodiazepinone; organochlorine compound	anxiolytic drug; environmental contaminant; xenobiotic
oxprenolol Oxprenolol: A beta-adrenergic antagonist used in the treatment of hypertension, angina pectoris, arrhythmias, and anxiety.	2.06	1	0	aromatic ether
pantoprazole Pantoprazole: 2-pyridinylmethylsulfinylbenzimidazole proton pump inhibitor that is used in the treatment of GASTROESOPHAGEAL REFLUX and PEPTIC ULCER.. pantoprazole : A member of the class of benzimidazoles that is 1H-benzimidazole substituted by a difluoromethoxy group at position 5 and a [(3,4-dimethoxypyridin-2-yl)methyl]sulfinyl group at position 2.	2.07	1	0	aromatic ether; benzimidazoles; organofluorine compound; pyridines; sulfoxide	anti-ulcer drug; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; environmental contaminant; xenobiotic
papaverine Papaverine: An alkaloid found in opium but not closely related to the other opium alkaloids in its structure or pharmacological actions. It is a direct-acting smooth muscle relaxant used in the treatment of impotence and as a vasodilator, especially for cerebral vasodilation. The mechanism of its pharmacological actions is not clear, but it apparently can inhibit phosphodiesterases and it may have direct actions on calcium channels.. papaverine : A benzylisoquinoline alkaloid that is isoquinoline substituted by methoxy groups at positions 6 and 7 and a 3,4-dimethoxybenzyl group at position 1. It has been isolated from Papaver somniferum.	2.89	4	0	benzylisoquinoline alkaloid; dimethoxybenzene; isoquinolines	antispasmodic drug; vasodilator agent
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'.	1.99	1	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.	2.64	3	0	barbiturates	GABAA receptor agonist
pentoxifylline [no description available]	2.69	3	0	oxopurine
phenacetin Saridon: contains phenacetin, caffeine, propyphenazone & pyrithyldione	2.75	3	0	acetamides; aromatic ether	cyclooxygenase 3 inhibitor; non-narcotic analgesic; peripheral nervous system drug
phenobarbital Phenobarbital: A barbituric acid derivative that acts as a nonselective central nervous system depressant. It potentiates GAMMA-AMINOBUTYRIC ACID action on GABA-A RECEPTORS, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations.. phenobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and phenyl groups.	6.65	28	0	barbiturates	anticonvulsant; drug allergen; excitatory amino acid antagonist; sedative
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.	3.36	7	0	2,1-benzoxathiole; arenesulfonate ester; phenols; sultone	acid-base indicator; diagnostic agent; two-colour indicator
4-phenylbutyric acid 4-phenylbutyric acid: RN refers to the parent cpd. 4-phenylbutyric acid : A monocarboxylic acid the structure of which is that of butyric acid substituted with a phenyl group at C-4. It is a histone deacetylase inhibitor that displays anticancer activity. It inhibits cell proliferation, invasion and migration and induces apoptosis in glioma cells. It also inhibits protein isoprenylation, depletes plasma glutamine, increases production of foetal haemoglobin through transcriptional activation of the gamma-globin gene and affects hPPARgamma activation.	2.49	2	0	monocarboxylic acid	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor; prodrug
phenylbutazone Phenylbutazone: A butyl-diphenyl-pyrazolidinedione that has anti-inflammatory, antipyretic, and analgesic activities. It has been used in ANKYLOSING SPONDYLITIS; RHEUMATOID ARTHRITIS; and REACTIVE ARTHRITIS.. phenylbutazone : A member of the class of pyrazolidines that is 1,2-diphenylpyrazolidine-3,5-dione carrying a butyl group at the 4-position.	2.07	1	0	pyrazolidines	antirheumatic drug; EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor; metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; peripheral nervous system drug
phenylmethylsulfonyl fluoride Phenylmethylsulfonyl Fluoride: An enzyme inhibitor that inactivates IRC-50 arvin, subtilisin, and the fatty acid synthetase complex.. phenylmethanesulfonyl fluoride : An acyl fluoride with phenylmethanesulfonyl as the acyl group.	2.69	3	0	acyl fluoride	serine proteinase inhibitor
phloretin [no description available]	1.96	1	0	dihydrochalcones	antineoplastic agent; plant metabolite
pilsicainide pilsicainide: structure given in first source. pilsicainide : A secondary carboxamide resulting from the formal condensation of the amino group of 2,6-dimethylaniline with the carboxy group of (tetrahydro-1H-pyrrolizin-7a(5H)-yl)acetic acid. It is a sodium channel blocker which is used as an antiarrhythmic drug for the management of atrial tachyarrhythmias in Japan.	3.57	2	0	organic heterobicyclic compound; secondary carboxamide	anti-arrhythmia drug; sodium channel blocker
pindolol Pindolol: A moderately lipophilic beta blocker (ADRENERGIC BETA-ANTAGONISTS). It is non-cardioselective and has intrinsic sympathomimetic actions, but little membrane-stabilizing activity. (From Martindale, The Extra Pharmocopoeia, 30th ed, p638). pindolol : A member of the class of indols which is the 2-hydroxy-3-(isopropylamino)propyl ether derivative of 1H-indol-4-ol.	3.85	3	0	indoles; secondary amine	antiglaucoma drug; antihypertensive agent; beta-adrenergic antagonist; serotonergic antagonist; vasodilator agent
pioglitazone Pioglitazone: A thiazolidinedione and PPAR GAMMA agonist that is used in the treatment of TYPE 2 DIABETES MELLITUS.. pioglitazone : A member of the class of thiazolidenediones that is 1,3-thiazolidine-2,4-dione substituted by a benzyl group at position 5 which in turn is substituted by a 2-(5-ethylpyridin-2-yl)ethoxy group at position 4 of the phenyl ring. It exhibits hypoglycemic activity.	3.19	5	0	aromatic ether; pyridines; thiazolidinediones	antidepressant; cardioprotective agent; EC 2.7.1.33 (pantothenate kinase) inhibitor; EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor; ferroptosis inhibitor; geroprotector; hypoglycemic agent; insulin-sensitizing drug; PPARgamma agonist; xenobiotic
pirenzepine Pirenzepine: An antimuscarinic agent that inhibits gastric secretion at lower doses than are required to affect gastrointestinal motility, salivary, central nervous system, cardiovascular, ocular, and urinary function. It promotes the healing of duodenal ulcers and due to its cytoprotective action is beneficial in the prevention of duodenal ulcer recurrence. It also potentiates the effect of other antiulcer agents such as CIMETIDINE and RANITIDINE. It is generally well tolerated by patients.	7.9	4	0	pyridobenzodiazepine	anti-ulcer drug; antispasmodic drug; muscarinic antagonist
potassium chloride Potassium Chloride: A white crystal or crystalline powder used in BUFFERS; FERTILIZERS; and EXPLOSIVES. It can be used to replenish ELECTROLYTES and restore WATER-ELECTROLYTE BALANCE in treating HYPOKALEMIA.. potassium chloride : A metal chloride salt with a K(+) counterion.	2.65	3	0	inorganic chloride; inorganic potassium salt; potassium salt	fertilizer
practolol Practolol: A beta-1 adrenergic antagonist that has been used in the emergency treatment of CARDIAC ARRYTHMIAS.. practolol : N-(4-Hydroxyphenyl)acetamide in which the hydrogen of the phenolic hydroxy group is substituted by a 3-(isopropylaminoamino)-2-hydroxypropyl group. A selective beta blocker, it has been used in the emergency treatment of cardiac arrhythmias.	2.06	1	0	acetamides; ethanolamines; propanolamine; secondary alcohol; secondary amino compound	anti-arrhythmia drug; beta-adrenergic antagonist
pramoxine pramoxine: RN given refers to parent cpd; structure. pramocaine : A member of the class of morpholines that is morpholine substituted at the nitrogen atom by a 3-(4-butoxyphenoxy)propyl group.	2.04	1	0	aromatic ether; morpholines	local anaesthetic
ono 1078 pranlukast: SRS-A antagonist; leukotriene D4 receptor antagonist	2	1	0	chromones
pyranoprofen pyranoprofen: RN given refers to unlabled parent cpd; structure given in first source	2.06	1	0	pyridochromene
prazosin Prazosin: A selective adrenergic alpha-1 antagonist used in the treatment of HEART FAILURE; HYPERTENSION; PHEOCHROMOCYTOMA; RAYNAUD DISEASE; PROSTATIC HYPERTROPHY; and URINARY RETENTION.. prazosin : A member of the class of piperazines that is piperazine substituted by a furan-2-ylcarbonyl group and a 4-amino-6,7-dimethoxyquinazolin-2-yl group at positions 1 and 4 respectively.	3.15	5	0	aromatic ether; furans; monocarboxylic acid amide; piperazines; quinazolines	alpha-adrenergic antagonist; antihypertensive agent; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
proadifen Proadifen: An inhibitor of drug metabolism and CYTOCHROME P-450 ENZYME SYSTEM activity.	1.95	1	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.	5.66	25	0	benzoic acids; sulfonamide	uricosuric drug
probucol Probucol: A drug used to lower LDL and HDL cholesterol yet has little effect on serum-triglyceride or VLDL cholesterol. (From Martindale, The Extra Pharmacopoeia, 30th ed, p993).. probucol : A dithioketal that is propane-2,2-dithiol in which the hydrogens attached to both sulfur atoms are replaced by 3,5-di-tert-butyl-4-hydroxyphenyl groups. An anticholesteremic drug with antioxidant and anti-inflammatory properties, it is used to treat high levels of cholesterol in blood.	7.11	1	0	dithioketal; polyphenol	anti-inflammatory drug; anticholesteremic drug; antilipemic drug; antioxidant; cardiovascular drug
procainamide Procainamide: A class Ia antiarrhythmic drug that is structurally-related to PROCAINE.. procainamide : A benzamide that is 4-aminobenzamide substituted on the amide N by a 2-(diethylamino)ethyl group. It is a pharmaceutical antiarrhythmic agent used for the medical treatment of cardiac arrhythmias.	4.46	7	0	benzamides	anti-arrhythmia drug; platelet aggregation inhibitor; sodium channel blocker
procaine Procaine: A local anesthetic of the ester type that has a slow onset and a short duration of action. It is mainly used for infiltration anesthesia, peripheral nerve block, and spinal block. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1016).. procaine : A benzoate ester, formally the result of esterification of 4-aminobenzoic acid with 2-diethylaminoethanol but formed experimentally by reaction of ethyl 4-aminobenzoate with 2-diethylaminoethanol.	2.67	3	0	benzoate ester; substituted aniline; tertiary amino compound	central nervous system depressant; drug allergen; local anaesthetic; peripheral nervous system drug
procyclidine Procyclidine: A muscarinic antagonist that crosses the blood-brain barrier and is used in the treatment of drug-induced extrapyramidal disorders and in parkinsonism.. procyclidine : A tertiary alcohol that consists of propan-1-ol substituted by a cyclohexyl and a phenyl group at position 1 and a pyrrolidin-1-yl group at position 3.	2.04	1	0	pyrrolidines; tertiary alcohol	antidyskinesia agent; antiparkinson drug; muscarinic antagonist
proglumide Proglumide: A drug that exerts an inhibitory effect on gastric secretion and reduces gastrointestinal motility. It is used clinically in the drug therapy of gastrointestinal ulcers.. proglumide : A racemate composed of equal amounts of (R)- and (S)-proglumide. A non-selective CCK antagonist that was used primarily for treatment of stomach ulcers, but has been replaced by newer drugs.. N(2)-benzoyl-N,N-dipropyl-alpha-glutamine : A dicarboxylic acid monoamide obtained by formal condensation of the alpha-carboxy group of N-benzoylglutamic acid with dippropylamine.	3.59	9	0	benzamides; dicarboxylic acid monoamide; glutamine derivative; racemate	anti-ulcer drug; cholecystokinin antagonist; cholinergic antagonist; delta-opioid receptor agonist; drug metabolite; gastrointestinal drug; opioid analgesic; xenobiotic metabolite
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.	2.04	1	0	aromatic ketone; secondary alcohol; secondary amino compound	anti-arrhythmia drug
propantheline Propantheline: A muscarinic antagonist used as an antispasmodic, in rhinitis, in urinary incontinence, and in the treatment of ulcers. At high doses it has nicotinic effects resulting in neuromuscular blocking.	2.06	1	0	xanthenes
propidium Propidium: Quaternary ammonium analog of ethidium; an intercalating dye with a specific affinity to certain forms of DNA and, used as diiodide, to separate them in density gradients; also forms fluorescent complexes with cholinesterase which it inhibits.	1.97	1	0	phenanthridines; quaternary ammonium ion	fluorochrome; intercalator
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.	4.18	17	0	naphthalenes; propanolamine; secondary amine	anti-arrhythmia drug; antihypertensive agent; anxiolytic drug; beta-adrenergic antagonist; environmental contaminant; human blood serum metabolite; vasodilator agent; xenobiotic
protoporphyrin ix protoporphyrin IX: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7685. protoporphyrin : A cyclic tetrapyrrole that consists of porphyrin bearing four methyl substituents at positions 3, 8, 13 and 17, two vinyl substituents at positions 7 and 12 and two 2-carboxyethyl substituents at positions 2 and 18. The parent of the class of protoporphyrins.	1.97	1	0
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.	3.05	5	0	aromatic ether; ethylenediamine derivative	H1-receptor antagonist
ranitidine [no description available]	3.84	3	0	aralkylamine
opc 12759 rebamipide: structure in first source; RN refers to (+-)-isomer; inhibits gastric xanthine oxidase	2.93	4	0	secondary carboxamide
ritanserin Ritanserin: A selective and potent serotonin-2 antagonist that is effective in the treatment of a variety of syndromes related to anxiety and depression. The drug also improves the subjective quality of sleep and decreases portal pressure.. ritanserin : A thiazolopyrimidine that is 5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one which is substituted at position 7 by a methyl group and at position 6 by a 2-{4-[bis(4-fluorophenyl)methylidene]piperidin-1-yl}ethyl group. A potent and long-acting seratonin (5-hydroxytryptamine, 5-HT) antagonist of the subtype 5-HT2 (Ki = 0.39 nM), it is used in the treatment of a variety of disorders including anxiety, depression and schizophrenia. It has little sedative action.	2.04	1	0	organofluorine compound; piperidines; thiazolopyrimidine	antidepressant; antipsychotic agent; anxiolytic drug; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; serotonergic antagonist
rofecoxib [no description available]	2.03	1	0	butenolide; sulfone	analgesic; cyclooxygenase 2 inhibitor; non-steroidal anti-inflammatory drug
rolipram [no description available]	2.05	1	0	pyrrolidin-2-ones	antidepressant; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor
s-methylisothiopseudouronium S-methylisothiopseudouronium: inhibits nitric oxide synthase; structure in first source	2.44	2	0
sanguinarine benzophenanthridine alkaloid : A specific group of isoquinoline alkaloids that occur only in higher plants and are constituents mainly of the Papaveraceae family.	2.07	1	0	alkaloid antibiotic; benzophenanthridine alkaloid; botanical anti-fungal agent
sb 202190 4-(4-fluorophenyl)-2-(4-hydroxyphenyl)-5-(4-pyridyl)imidazole: structure given in first source; inhibits p38 MAP kinase	2	1	0	imidazoles; organofluorine compound; phenols; pyridines	apoptosis inducer; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor
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.	1.95	1	0	barbiturates	anaesthesia adjuvant; GABA modulator; sedative
sodium fluoride [no description available]	2.68	3	0	fluoride salt	mutagen
ipodate Ipodate: Ionic monomeric contrast media. Usually the sodium or calcium salts are used for examination of the gall bladder and biliary tract. (From Martindale, The Extra Pharmacopoeia, 30th ed, p704)	1.96	1	0
sotalol Sotalol: An adrenergic beta-antagonist that is used in the treatment of life-threatening arrhythmias.. sotalol : A sulfonamide that is N-phenylmethanesulfonamide in which the phenyl group is substituted at position 4 by a 1-hydroxy-2-(isopropylamino)ethyl group. It has both beta-adrenoreceptor blocking (Vaughan Williams Class II) and cardiac action potential duration prolongation (Vaughan Williams Class III) antiarrhythmic properties. It is used (usually as the hydrochloride salt) for the management of ventricular and supraventricular arrhythmias.	2.75	3	0	ethanolamines; secondary alcohol; secondary amino compound; sulfonamide	anti-arrhythmia drug; beta-adrenergic antagonist; environmental contaminant; xenobiotic
stearic acid octadecanoic acid : A C18 straight-chain saturated fatty acid component of many animal and vegetable lipids. As well as in the diet, it is used in hardening soaps, softening plastics and in making cosmetics, candles and plastics.	2.95	4	0	long-chain fatty acid; saturated fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; human metabolite; plant metabolite
imatinib [no description available]	3.15	1	0	aromatic amine; benzamides; N-methylpiperazine; pyridines; pyrimidines	antineoplastic agent; apoptosis inducer; tyrosine kinase inhibitor
vorinostat Vorinostat: A hydroxamic acid and anilide derivative that acts as a HISTONE DEACETYLASE inhibitor. It is used in the treatment of CUTANEOUS T-CELL LYMPHOMA and SEZARY SYNDROME.. vorinostat : A dicarboxylic acid diamide comprising suberic (octanedioic) acid coupled to aniline and hydroxylamine. A histone deacetylase inhibitor, it is marketed under the name Zolinza for the treatment of cutaneous T cell lymphoma (CTCL).	2.07	1	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.	2.37	2	0	aromatic ether; pyrimidines; substituted aniline; sulfonamide antibiotic; sulfonamide	antiinfective agent; antimicrobial agent; drug allergen; environmental contaminant; xenobiotic
sulfaguanidine Sulfaguanidine: A sulfanilamide antimicrobial agent that is used to treat enteric infections.. sulfaguanidine : A sulfonamide incorporating a guanidine moiety used to block the synthesis of folic acid; mostly used in veterinary medicine	2.37	2	0	sulfonamide antibiotic	antiinfective agent
sulfamerazine [no description available]	2.13	1	0	pyrimidines; sulfonamide antibiotic; sulfonamide	antiinfective agent; drug allergen
sulfanitran [no description available]	2.04	1	0	sulfonamide
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.	2.07	1	0	primary amino compound; pyrazoles; substituted aniline; sulfonamide antibiotic; sulfonamide	antibacterial drug; EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor; EC 1.14.13.67 (quinine 3-monooxygenase) inhibitor; P450 inhibitor
sulfasalazine Sulfasalazine: A drug that is used in the management of inflammatory bowel diseases. Its activity is generally considered to lie in its metabolic breakdown product, 5-aminosalicylic acid (see MESALAMINE) released in the colon. (From Martindale, The Extra Pharmacopoeia, 30th ed, p907). sulfasalazine : An azobenzene consisting of diphenyldiazene having a carboxy substituent at the 4-position, a hydroxy substituent at the 3-position and a 2-pyridylaminosulphonyl substituent at the 4'-position.	6	8	1
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.	2.04	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.	2.43	2	0	pyrazolidines; sulfoxide	uricosuric drug
sulfobromophthalein Sulfobromophthalein: A phenolphthalein that is used as a diagnostic aid in hepatic function determination.	7.23	95	1	2-benzofurans; organobromine compound; organosulfonic acid; phenols	dye
sulpiride Sulpiride: A dopamine D2-receptor antagonist. It has been used therapeutically as an antidepressant, antipsychotic, and as a digestive aid. (From Merck Index, 11th ed). sulpiride : A member of the class of benzamides obtained from formal condensation between the carboxy group of 2-methoxy-5-sulfamoylbenzoic acid and the primary amino group of (1-ethylpyrrolidin-2-yl)methylamine.	2.06	1	0	benzamides; N-alkylpyrrolidine; sulfonamide	antidepressant; antiemetic; antipsychotic agent; dopaminergic antagonist
sumatriptan Sumatriptan: A serotonin agonist that acts selectively at 5HT1 receptors. It is used in the treatment of MIGRAINE DISORDERS.. sumatriptan : A sulfonamide that consists of N,N-dimethyltryptamine bearing an additional (N-methylsulfamoyl)methyl substituent at position 5. Selective agonist for a vascular 5-HT1 receptor subtype (probably a member of the 5-HT1D family). Used (in the form of its succinate salt) for the acute treatment of migraine with or without aura in adults.	2.44	2	0	sulfonamide; tryptamines	serotonergic agonist; vasoconstrictor agent
terazosin Terazosin: induces decreased blood pressure; used in the treatment of benign prostatic hyperplasia	2.04	1	0	furans; piperazines; primary amino compound; quinazolines	alpha-adrenergic antagonist; antihypertensive agent; antineoplastic agent
terbutaline Terbutaline: A selective beta-2 adrenergic agonist used as a bronchodilator and tocolytic.. terbutaline : A member of the class of phenylethanolamines that is catechol substituted at position 5 by a 2-(tert-butylamino)-1-hydroxyethyl group.	2.42	2	0	phenylethanolamines; resorcinols	anti-asthmatic drug; beta-adrenergic agonist; bronchodilator agent; EC 3.1.1.7 (acetylcholinesterase) inhibitor; hypoglycemic agent; sympathomimetic agent; tocolytic agent
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.	3.14	5	0	diarylmethane
tetracaine Tetracaine: A potent local anesthetic of the ester type used for surface and spinal anesthesia.. tetracaine : A benzoate ester in which 4-N-butylbenzoic acid and 2-(dimethylamino)ethanol have combined to form the ester bond; a local ester anaesthetic (ester caine) used for surface and spinal anaesthesia.	1.95	1	0	benzoate ester; tertiary amino compound	local anaesthetic
tetraethylammonium Tetraethylammonium: A potassium-selective ion channel blocker. (From J Gen Phys 1994;104(1):173-90)	4.61	8	0	quaternary ammonium ion
theobromine Theobromine: 3,7-Dimethylxanthine. The principle alkaloid in Theobroma cacao (the cacao bean) and other plants. A xanthine alkaloid that is used as a bronchodilator and as a vasodilator. It has a weaker diuretic activity than THEOPHYLLINE and is also a less powerful stimulant of smooth muscle. It has practically no stimulant effect on the central nervous system. It was formerly used as a diuretic and in the treatment of angina pectoris and hypertension. (From Martindale, The Extra Pharmacopoeia, 30th ed, pp1318-9). theobromine : A dimethylxanthine having the two methyl groups located at positions 3 and 7. A purine alkaloid derived from the cacao plant, it is found in chocolate, as well as in a number of other foods, and is a vasodilator, diuretic and heart stimulator.	1.97	1	0	dimethylxanthine	adenosine receptor antagonist; bronchodilator agent; food component; human blood serum metabolite; mouse metabolite; plant metabolite; vasodilator agent
thioridazine Thioridazine: A phenothiazine antipsychotic used in the management of PHYCOSES, including SCHIZOPHRENIA.. thioridazine : A phenothiazine derivative having a methylsulfanyl subsitituent at the 2-position and a (1-methylpiperidin-2-yl)ethyl] group at the N-10 position.	2.46	2	0	phenothiazines; piperidines	alpha-adrenergic antagonist; dopaminergic antagonist; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; first generation antipsychotic; H1-receptor antagonist; serotonergic antagonist
thiotepa Thiotepa: A very toxic alkylating antineoplastic agent also used as an insect sterilant. It causes skin, gastrointestinal, CNS, and bone marrow damage. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), thiotepa may reasonably be anticipated to be a carcinogen (Merck Index, 11th ed).	2.07	1	0	aziridines
thymeleatoxin thymeleatoxin: causes translocation & down-regulation of multiple protein kinase C isozymes	2.02	1	0
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.	2.06	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.	2.48	2	0	monochlorobenzenes; thienopyridine	anticoagulant; fibrin modulating drug; hematologic agent; P2Y12 receptor antagonist; platelet aggregation inhibitor
tinidazole Tinidazole: A nitroimidazole alkylating agent that is used as an antitrichomonal agent against TRICHOMONAS VAGINALIS; ENTAMOEBA HISTOLYTICA; and GIARDIA LAMBLIA infections. It also acts as an antibacterial agent for the treatment of BACTERIAL VAGINOSIS and anaerobic bacterial infections.. tinidazole : 1H-imidazole substituted at C-1 by a (2-ethylsulfonyl)ethyl group, at C-2 by a methyl group and at C-5 by a nitro group. It is used as an antiprotozoal, antibacterial agent.	2.04	1	0	imidazoles	antiamoebic agent; antibacterial drug; antiparasitic agent; antiprotozoal drug
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.	2.07	1	0	N-sulfonylurea	human metabolite; hypoglycemic agent; insulin secretagogue; potassium channel blocker
ultram 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol : A tertiary alcohol that is cyclohexanol substituted at positions 1 and 2 by 3-methoxyphenyl and dimethylaminomethyl groups respectively.	2.04	1	0	aromatic ether; tertiary alcohol; tertiary amino compound
tranexamic acid Tranexamic Acid: Antifibrinolytic hemostatic used in severe hemorrhage.	2.49	2	0	amino acid
trequinsin trequinsin: RN given refers to parent cpd; structure given in first source	2.01	1	0	pyridopyrimidine
triazolam Triazolam: A short-acting benzodiazepine used in the treatment of insomnia. Some countries temporarily withdrew triazolam from the market because of concerns about adverse reactions, mostly psychological, associated with higher dose ranges. Its use at lower doses with appropriate care and labeling has been reaffirmed by the FDA and most other countries.	2.07	1	0	triazolobenzodiazepine	sedative
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.	2.97	4	0	aminopyrimidine; methoxybenzenes	antibacterial drug; diuretic; drug allergen; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; environmental contaminant; xenobiotic
troglitazone Troglitazone: A chroman and thiazolidinedione derivative that acts as a PEROXISOME PROLIFERATOR-ACTIVATED RECEPTORS (PPAR) agonist. It was formerly used in the treatment of TYPE 2 DIABETES MELLITUS, but has been withdrawn due to hepatotoxicity.	9.94	11	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.	3.15	1	0	aminopyridine; indolecarboxamide; N-acylpiperazine; sulfonamide	antiviral drug; HIV-1 reverse transcriptase inhibitor
urethane [no description available]	8.05	5	0	carbamate ester	fungal metabolite; mutagen
ici 204,219 zafirlukast: a leukotriene D4 receptor antagonist	3.51	1	0	carbamate ester; indoles; N-sulfonylcarboxamide	anti-asthmatic agent; leukotriene antagonist
cn 100 CN 100: structure given in first source	2.06	1	0	organic molecular entity
fr 74366 [no description available]	2.01	1	0
oxyphenonium Oxyphenonium: A quaternary ammonium anticholinergic agent with peripheral side effects similar to those of ATROPINE. It is used as an adjunct in the treatment of gastric and duodenal ulcer, and to relieve visceral spasms. The drug has also been used in the form of eye drops for mydriatic effect.	1.97	1	0	acylcholine
corticosterone [no description available]	8.86	12	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
prednisolone Prednisolone: A glucocorticoid with the general properties of the corticosteroids. It is the drug of choice for all conditions in which routine systemic corticosteroid therapy is indicated, except adrenal deficiency states.. prednisolone : A glucocorticoid that is prednisone in which the oxo group at position 11 has been reduced to the corresponding beta-hydroxy group. It is a drug metabolite of prednisone.	3.37	7	0	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	adrenergic agent; anti-inflammatory drug; antineoplastic agent; drug metabolite; environmental contaminant; immunosuppressive agent; xenobiotic
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.	2.89	4	0	16alpha-hydroxy steroid; 17beta-hydroxy steroid; 3-hydroxy steroid	estrogen; human metabolite; human xenobiotic metabolite; mouse metabolite
reserpine Reserpine: An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria. Reserpine inhibits the uptake of norepinephrine into storage vesicles resulting in depletion of catecholamines and serotonin from central and peripheral axon terminals. It has been used as an antihypertensive and an antipsychotic as well as a research tool, but its adverse effects limit its clinical use.. reserpine : An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria.	3.13	5	0	alkaloid ester; methyl ester; yohimban alkaloid	adrenergic uptake inhibitor; antihypertensive agent; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; environmental contaminant; first generation antipsychotic; plant metabolite; xenobiotic
phentolamine Phentolamine: A nonselective alpha-adrenergic antagonist. It is used in the treatment of hypertension and hypertensive emergencies, pheochromocytoma, vasospasm of RAYNAUD DISEASE and frostbite, clonidine withdrawal syndrome, impotence, and peripheral vascular disease.. phentolamine : A substituted aniline that is 3-aminophenol in which the hydrogens of the amino group are replaced by 4-methylphenyl and 4,5-dihydro-1H-imidazol-2-ylmethyl groups respectively. An alpha-adrenergic antagonist, it is used for the treatment of hypertension.	1.97	1	0	imidazoles; phenols; substituted aniline; tertiary amino compound	alpha-adrenergic antagonist; vasodilator agent
thymidine [no description available]	3.09	5	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite
floxuridine Floxuridine: An antineoplastic antimetabolite that is metabolized to fluorouracil when administered by rapid injection; when administered by slow, continuous, intra-arterial infusion, it is converted to floxuridine monophosphate. It has been used to treat hepatic metastases of gastrointestinal adenocarcinomas and for palliation in malignant neoplasms of the liver and gastrointestinal tract.. floxuridine : A pyrimidine 2'-deoxyribonucleoside compound having 5-fluorouracil as the nucleobase; used to treat hepatic metastases of gastrointestinal adenocarcinomas and for palliation in malignant neoplasms of the liver and gastrointestinal tract.	2.1	1	0	nucleoside analogue; organofluorine compound; pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent; antiviral drug; radiosensitizing agent
3,3',5-triiodothyroacetic acid tiratricol : A monocarboxylic acid that is (4-hydroxy-3,5-diiodophenyl)acetic acid in which the phenolic hydroxy group has been replaced by a 4-hydroxy-3-iodophenoxy group. It is a thyroid hormone analogue that has been used in the treatment of thyroid hormone resistance syndrome.	3.59	2	0
hydroxyproline Hydroxyproline: A hydroxylated form of the imino acid proline. A deficiency in ASCORBIC ACID can result in impaired hydroxyproline formation.. hydroxyproline : A proline derivative that is proline substituted by at least one hydroxy group.	2.38	2	0	4-hydroxyproline; L-alpha-amino acid zwitterion	human metabolite; mouse metabolite; plant 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.	4.19	17	0	2-halophenol; iodophenol; L-phenylalanine derivative; non-proteinogenic L-alpha-amino acid; thyroxine zwitterion; thyroxine	antithyroid drug; human metabolite; mouse metabolite; thyroid hormone
carbachol Carbachol: A slowly hydrolyzed CHOLINERGIC AGONIST that acts at both MUSCARINIC RECEPTORS and NICOTINIC RECEPTORS.	2.66	3	0	ammonium salt; carbamate ester	cardiotonic drug; miotic; muscarinic agonist; nicotinic acetylcholine receptor agonist; non-narcotic analgesic
spironolactone Spironolactone: A potassium sparing diuretic that acts by antagonism of aldosterone in the distal renal tubules. It is used mainly in the treatment of refractory edema in patients with congestive heart failure, nephrotic syndrome, or hepatic cirrhosis. Its effects on the endocrine system are utilized in the treatments of hirsutism and acne but they can lead to adverse effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p827). spironolactone : A steroid lactone that is 17alpha-pregn-4-ene-21,17-carbolactone substituted by an oxo group at position 3 and an alpha-acetylsulfanyl group at position 7.	3.24	6	0	3-oxo-Delta(4) steroid; oxaspiro compound; steroid lactone; thioester	aldosterone antagonist; antihypertensive agent; diuretic; environmental contaminant; xenobiotic
aldosterone [no description available]	2.39	2	0	11beta-hydroxy steroid; 18-oxo steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid hormone; mineralocorticoid; primary alpha-hydroxy ketone; steroid aldehyde	human metabolite; mouse metabolite
norethandrolone Norethandrolone: A synthetic hormone with anabolic and androgenic properties and moderate progestational activity.	1.95	1	0	corticosteroid hormone
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.	2.41	2	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
estrone Hydroxyestrones: Estrone derivatives substituted with one or more hydroxyl groups in any position. They are important metabolites of estrone and other estrogens.	5.99	34	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]	2.41	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.	2.04	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.	3.26	6	0	17-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; androstanoid	androgen; human metabolite; mouse metabolite
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.	1.96	1	0	2-acetamidofluorenes	antimitotic; carcinogenic agent; epitope; mutagen
penicillin g Penicillin G: A penicillin derivative commonly used in the form of its sodium or potassium salts in the treatment of a variety of infections. It is effective against most gram-positive bacteria and against gram-negative cocci. It has also been used as an experimental convulsant because of its actions on GAMMA-AMINOBUTYRIC ACID mediated synaptic transmission.. benzylpenicillin : A penicillin in which the substituent at position 6 of the penam ring is a phenylacetamido group.	3.8	11	0	penicillin allergen; penicillin	antibacterial drug; drug allergen; epitope
dimethylphenylpiperazinium iodide Dimethylphenylpiperazinium Iodide: A selective nicotinic cholinergic agonist used as a research tool. DMPP activates nicotinic receptors in autonomic ganglia but has little effect at the neuromuscular junction.	2	1	0	N-arylpiperazine; organic iodide salt; piperazinium salt; quaternary ammonium salt	nicotinic acetylcholine receptor agonist
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.	4.01	14	0	2-halophenol; amino acid zwitterion; iodophenol; iodothyronine	human metabolite; mouse metabolite; thyroid hormone
isoflurophate Isoflurophate: A di-isopropyl-fluorophosphate which is an irreversible cholinesterase inhibitor used to investigate the NERVOUS SYSTEM.	2.36	2	0	dialkyl phosphate
biguanides Biguanides: Derivatives of biguanide (the structure formula HN(C(NH)NH2)2) that are primarily used as oral HYPOGLYCEMIC AGENTS for the treatment of DIABETES MELLITUS, TYPE 2 and PREDIABETES.. biguanides : A class of oral hypoglycemic drugs used for diabetes mellitus or prediabetes treatment. They have a structure based on the 2-carbamimidoylguanidine skeleton.	2.35	2	0	guanidines
carbon tetrachloride Carbon Tetrachloride: A solvent for oils, fats, lacquers, varnishes, rubber waxes, and resins, and a starting material in the manufacturing of organic compounds. Poisoning by inhalation, ingestion or skin absorption is possible and may be fatal. (Merck Index, 11th ed). tetrachloromethane : A chlorocarbon that is methane in which all the hydrogens have been replaced by chloro groups.	3.4	7	0	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
alanine Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.	5.72	27	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.	3.6	9	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.	1.93	1	0	ortho-fused polycyclic arene; tetraphenes
4-nitroquinoline-1-oxide 4-nitroquinoline N-oxide : A quinoline N-oxide carrying a nitro substituent at position 4.	2	1	0	C-nitro compound; quinoline N-oxide	carcinogenic agent
chloramphenicol Amphenicol: Chloramphenicol and its derivatives.	3.28	6	0	C-nitro compound; carboxamide; diol; organochlorine compound	antibacterial drug; antimicrobial agent; Escherichia coli metabolite; geroprotector; Mycoplasma genitalium metabolite; protein synthesis inhibitor
aspartic acid Aspartic Acid: One of the non-essential amino acids commonly occurring in the L-form. It is found in animals and plants, especially in sugar cane and sugar beets. It may be a neurotransmitter.. aspartic acid : An alpha-amino acid that consists of succinic acid bearing a single alpha-amino substituent. L-aspartic acid : The L-enantiomer of aspartic acid.	2.9	4	0	aspartate family amino acid; aspartic acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; mouse metabolite; neurotransmitter
glutamine Glutamine: A non-essential amino acid present abundantly throughout the body and is involved in many metabolic processes. It is synthesized from GLUTAMIC ACID and AMMONIA. It is the principal carrier of NITROGEN in the body and is an important energy source for many cells.. L-glutamine : An optically active form of glutamine having L-configuration.. glutamine : An alpha-amino acid that consists of butyric acid bearing an amino substituent at position 2 and a carbamoyl substituent at position 4.	9.06	15	0	amino acid zwitterion; glutamine family amino acid; glutamine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	EC 1.14.13.39 (nitric oxide synthase) inhibitor; Escherichia coli metabolite; human metabolite; metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
lysine Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.	2.89	4	0	aspartate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; lysine; organic molecular entity; proteinogenic amino acid	algal metabolite; anticonvulsant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
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.	2.87	4	0	pseudohalide anion	EC 1.9.3.1 (cytochrome c oxidase) inhibitor
vincristine [no description available]	3.12	5	0	acetate ester; formamides; methyl ester; organic heteropentacyclic compound; organic heterotetracyclic compound; tertiary alcohol; tertiary amino compound; vinca alkaloid	antineoplastic agent; drug; microtubule-destabilising agent; plant metabolite; tubulin modulator
physostigmine Physostigmine: A cholinesterase inhibitor that is rapidly absorbed through membranes. It can be applied topically to the conjunctiva. It also can cross the blood-brain barrier and is used when central nervous system effects are desired, as in the treatment of severe anticholinergic toxicity.	2.87	4	0	carbamate ester; indole alkaloid	antidote to curare poisoning; EC 3.1.1.8 (cholinesterase) inhibitor; miotic
sucrose Saccharum: A plant genus of the family POACEAE widely cultivated in the tropics for the sweet cane that is processed into sugar.	4.83	34	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.	9.33	20	0	17-hydroxy steroid; 3-hydroxy steroid; terminal acetylenic compound	xenoestrogen
tubocurarine Tubocurarine: A neuromuscular blocker and active ingredient in CURARE; plant based alkaloid of Menispermaceae.. tubocurarine : A benzylisoquinoline alkaloid muscle relaxant which constitutes the active component of curare.. isoquinoline alkaloid : Any alkaloid that has a structure based on an isoquinoline nucleus. They are derived from the amino acids like tyrosine and phenylalanine.	2.37	2	0	bisbenzylisoquinoline alkaloid	drug allergen; muscle relaxant; nicotinic antagonist
9,10-dimethyl-1,2-benzanthracene 9,10-Dimethyl-1,2-benzanthracene: Polycyclic aromatic hydrocarbon found in tobacco smoke that is a potent carcinogen.. 7,12-dimethyltetraphene : A tetraphene having methyl substituents at the 7- and 12-positions. It is a potent carcinogen and is present in tobacco smoke.	2.34	2	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.	4.27	7	0	pyrazolone; tertiary amino compound	antipyretic; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
adenosine diphosphate Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.	3.07	5	0	adenosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	fundamental metabolite; human metabolite
cephalothin Cephalothin: A cephalosporin antibiotic.. cefalotin : A semisynthetic, first-generation cephalosporin antibiotic with acetoxymethyl and (2-thienylacetyl)nitrilo moieties at positions 3 and 7, respectively, of the core structure. Administered parenterally during surgery and to treat a wide spectrum of blood infections.	2.64	3	0	azabicycloalkene; beta-lactam antibiotic allergen; carboxylic acid; cephalosporin; semisynthetic derivative; thiophenes	antibacterial drug; antimicrobial agent
kanamycin a Kanamycin: Antibiotic complex produced by Streptomyces kanamyceticus from Japanese soil. Comprises 3 components: kanamycin A, the major component, and kanamycins B and C, the minor components.. kanamycin : Kanamycin is a naturally occurring antibiotic complex from Streptomyces kanamyceticus that consists of several components: kanamycin A, the major component (also usually designated as kanamycin), and kanamycins B, C, D and X the minor components.	2.45	2	0	kanamycins	bacterial metabolite
galactose galactopyranose : The pyranose form of galactose.	4.03	15	0	D-galactose; galactopyranose	Escherichia coli metabolite; mouse metabolite
carbostyril Quinolones: A group of derivatives of naphthyridine carboxylic acid, quinoline carboxylic acid, or NALIDIXIC ACID.. quinolin-2(1H)-one : A quinolone that is 1,2-dihydroquinoline substituted by an oxo group at position 2.	2.93	4	0	monohydroxyquinoline; quinolone	bacterial xenobiotic metabolite
phenylephrine Phenylephrine: An alpha-1 adrenergic agonist used as a mydriatic, nasal decongestant, and cardiotonic agent.. phenylephrine : A member of the class of the class of phenylethanolamines that is (1R)-2-(methylamino)-1-phenylethan-1-ol carrying an additional hydroxy substituent at position 3 on the phenyl ring.	2.38	2	0	phenols; phenylethanolamines; secondary amino compound	alpha-adrenergic agonist; cardiotonic drug; mydriatic agent; nasal decongestant; protective agent; sympathomimetic agent; vasoconstrictor agent
levodopa Levodopa: The naturally occurring form of DIHYDROXYPHENYLALANINE and the immediate precursor of DOPAMINE. Unlike dopamine itself, it can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to DOPAMINE. It is used for the treatment of PARKINSONIAN DISORDERS and is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system.. L-dopa : An optically active form of dopa having L-configuration. Used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease	2.06	1	0	amino acid zwitterion; dopa; L-tyrosine derivative; non-proteinogenic L-alpha-amino acid	allelochemical; antidyskinesia agent; antiparkinson drug; dopaminergic agent; hapten; human metabolite; mouse metabolite; neurotoxin; plant growth retardant; plant metabolite; prodrug
edetic acid Edetic Acid: A chelating agent that sequesters a variety of polyvalent cations such as CALCIUM. It is used in pharmaceutical manufacturing and as a food additive.	4.22	18	0	ethylenediamine derivative; polyamino carboxylic acid; tetracarboxylic acid	anticoagulant; antidote; chelator; copper chelator; geroprotector
tributyrin tributyrin: structure. tributyrin : A triglyceride obtained by formal acylation of the three hydroxy groups of glycerol by butyric acid.	1.97	1	0	butyrate ester; triglyceride	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor; prodrug; protective agent
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.	2.49	2	0	benzenes; primary alcohol	Aspergillus metabolite; fragrance; plant growth retardant; plant metabolite; Saccharomyces cerevisiae metabolite
tyrosine Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.	2.68	3	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; proteinogenic amino acid; tyrosine	EC 1.3.1.43 (arogenate dehydrogenase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
cysteamine Cysteamine: A mercaptoethylamine compound that is endogenously derived from the COENZYME A degradative pathway. The fact that cysteamine is readily transported into LYSOSOMES where it reacts with CYSTINE to form cysteine-cysteamine disulfide and CYSTEINE has led to its use in CYSTINE DEPLETING AGENTS for the treatment of CYSTINOSIS.. cysteamine : An amine that consists of an ethane skeleton substituted with a thiol group at C-1 and an amino group at C-2.	2.66	3	0	amine; thiol	geroprotector; human metabolite; mouse metabolite; radiation protective agent
adenosine monophosphate Adenosine Monophosphate: Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position.	2.92	4	0	adenosine 5'-phosphate; purine ribonucleoside 5'-monophosphate	adenosine A1 receptor agonist; cofactor; EC 3.1.3.1 (alkaline phosphatase) inhibitor; EC 3.1.3.11 (fructose-bisphosphatase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
methylene blue Methylene Blue: A compound consisting of dark green crystals or crystalline powder, having a bronze-like luster. Solutions in water or alcohol have a deep blue color. Methylene blue is used as a bacteriologic stain and as an indicator. It inhibits GUANYLATE CYCLASE, and has been used to treat cyanide poisoning and to lower levels of METHEMOGLOBIN.. methylene blue : An organic chloride salt having 3,7-bis(dimethylamino)phenothiazin-5-ium as the counterion. A commonly used dye that also exhibits antioxidant, antimalarial, antidepressant and cardioprotective properties.	2.44	2	0	organic chloride salt	acid-base indicator; antidepressant; antimalarial; antimicrobial agent; antioxidant; cardioprotective agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 4.6.1.2 (guanylate cyclase) inhibitor; fluorochrome; histological dye; neuroprotective agent; physical tracer
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.	3.09	5	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
ethyl methanesulfonate Ethyl Methanesulfonate: An antineoplastic agent with alkylating properties. It also acts as a mutagen by damaging DNA and is used experimentally for that effect.. ethyl methanesulfonate : A methanesulfonate ester resulting from the formal condensation of methanesulfonic acid with ethanol.	2.03	1	0	methanesulfonate ester	alkylating agent; antineoplastic agent; carcinogenic agent; genotoxin; mutagen; teratogenic agent
2-aminoisobutyric acid 2-aminoisobutyric acid: RN given refers to unlabeled cpd. 2-aminoisobutyric acid : A rare, non-protein amino acid and end-product of pyrimidine metabolism, excreted in urine and found in some antibiotics of fungal origin. With the exception of a few bacteria, it is non-metabolisable, and therefore used in bioassays.	1.97	1	0	2,2-dialkylglycine zwitterion; 2,2-dialkylglycine
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.	2.08	1	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.	2.03	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
lactose Lactose: A disaccharide of GLUCOSE and GALACTOSE in human and cow milk. It is used in pharmacy for tablets, in medicine as a nutrient, and in industry.. lactose : A glycosylglucose disaccharide, found most notably in milk, that consists of D-galactose and D-glucose fragments bonded through a beta-1->4 glycosidic linkage. The glucose fragment can be in either the alpha- or beta-pyranose form, whereas the galactose fragment can only have the beta-pyranose form.. beta-lactose : The beta-anomer of lactose.	3.05	5	0	lactose
methionine Methionine: A sulfur-containing essential L-amino acid that is important in many body functions.. methionine : A sulfur-containing amino acid that is butyric acid bearing an amino substituent at position 2 and a methylthio substituent at position 4.	3.1	5	0	aspartate family amino acid; L-alpha-amino acid; methionine zwitterion; methionine; proteinogenic amino acid	antidote to paracetamol poisoning; human metabolite; micronutrient; mouse metabolite; nutraceutical
1,2-dipalmitoylphosphatidylcholine 1,2-Dipalmitoylphosphatidylcholine: Synthetic phospholipid used in liposomes and lipid bilayers to study biological membranes. It is also a major constituent of PULMONARY SURFACTANTS.	3.09	5	0
phenylalanine Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.	2.88	4	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; phenylalanine; proteinogenic amino acid	algal metabolite; EC 3.1.3.1 (alkaline phosphatase) inhibitor; Escherichia coli metabolite; human xenobiotic metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
colchicine (S)-colchicine : A colchicine that has (S)-configuration. It is a secondary metabolite, has anti-inflammatory properties and is used to treat gout, crystal-induced joint inflammation, familial Mediterranean fever, and many other conditions.	4.69	29	0	alkaloid; colchicine	anti-inflammatory agent; gout suppressant; mutagen
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.	3.92	13	0	antibiotic fungicide; cyclic ketone; dicarboximide; piperidine antibiotic; piperidones; secondary alcohol	anticoronaviral agent; bacterial metabolite; ferroptosis inhibitor; neuroprotective agent; protein synthesis inhibitor
egtazic acid Egtazic Acid: A chelating agent relatively more specific for calcium and less toxic than EDETIC ACID.. ethylene glycol bis(2-aminoethyl)tetraacetic acid : A diether that is ethylene glycol in which the hydrogens of the hydroxy groups have been replaced by 2-[bis(carboxymethyl)amino]ethyl group respectively.	3.07	5	0	diether; tertiary amino compound; tetracarboxylic acid	chelator
chloroform Chloroform: A commonly used laboratory solvent. It was previously used as an anesthetic, but was banned from use in the U.S. due to its suspected carcinogenicity.. chloroform : A one-carbon compound that is methane in which three of the hydrogens are replaced by chlorines.	2.39	2	0	chloromethanes; one-carbon compound	carcinogenic agent; central nervous system drug; inhalation anaesthetic; non-polar solvent; refrigerant
dimethylformamide Dimethylformamide: A formamide in which the amino hydrogens are replaced by methyl groups.. N,N-dimethylformamide : A member of the class of formamides that is formamide in which the amino hydrogens are replaced by methyl groups.	3.15	1	0	formamides; volatile organic compound	geroprotector; hepatotoxic agent; polar aprotic solvent
cycloserine Cycloserine: Antibiotic substance produced by Streptomyces garyphalus.. D-cycloserine : A 4-amino-1,2-oxazolidin-3-one that has R configuration. It is an antibiotic produced by Streptomyces garyphalus or S. orchidaceus and is used as part of a multi-drug regimen for the treatment of tuberculosis when resistance to, or toxicity from, primary drugs has developed. An analogue of D-alanine, it interferes with bacterial cell wall synthesis in the cytoplasm by competitive inhibition of L-alanine racemase (which forms D-alanine from L-alanine) and D-alanine--D-alanine ligase (which incorporates D-alanine into the pentapeptide required for peptidoglycan formation and bacterial cell wall synthesis).	2.96	4	0	4-amino-1,2-oxazolidin-3-one; organonitrogen heterocyclic antibiotic; organooxygen heterocyclic antibiotic; zwitterion	antiinfective agent; antimetabolite; antitubercular agent; metabolite; NMDA receptor agonist
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.	3.26	6	0	beta-lactam antibiotic; penicillin allergen; penicillin	antibacterial drug
mannitol [no description available]	5.85	23	1	mannitol	allergen; antiglaucoma drug; compatible osmolytes; Escherichia coli metabolite; food anticaking agent; food bulking agent; food humectant; food stabiliser; food thickening agent; hapten; metabolite; osmotic diuretic; sweetening agent
dithionitrobenzoic acid Dithionitrobenzoic Acid: A standard reagent for the determination of reactive sulfhydryl groups by absorbance measurements. It is used primarily for the determination of sulfhydryl and disulfide groups in proteins. The color produced is due to the formation of a thio anion, 3-carboxyl-4-nitrothiophenolate.. dithionitrobenzoic acid : An organic disulfide that results from the formal oxidative dimerisation of 2-nitro-5-thiobenzoic acid. An indicator used to quantify the number or concentration of thiol groups.	2.38	2	0	nitrobenzoic acid; organic disulfide	indicator
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.	2.36	2	0	C-nitro compound; organofluorine compound	agrochemical; allergen; chromatographic reagent; EC 2.7.3.2 (creatine kinase) inhibitor; protein-sequencing agent; spectrophotometric reagent
asparagine Asparagine: A non-essential amino acid that is involved in the metabolic control of cell functions in nerve and brain tissue. It is biosynthesized from ASPARTIC ACID and AMMONIA by asparagine synthetase. (From Concise Encyclopedia Biochemistry and Molecular Biology, 3rd ed). asparagine : An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 2-amino-2-oxoethyl group.	2.05	1	0	amino acid zwitterion; asparagine; aspartate family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
histidine Histidine: An essential amino acid that is required for the production of HISTAMINE.. L-histidine : The L-enantiomer of the amino acid histidine.. histidine : An alpha-amino acid that is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3.	3.11	5	0	amino acid zwitterion; histidine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
sulfobromophthalein sodium bromosulfophthalein sodium : An organic sodium salt that is the disodium salt of bromosulfophthalein.. bromosulfophthalein : An organosulfonic acid that consists of phthalide bearing four bromo substituents at positions 4, 5, 6 and 7 as well as two 4-hydroxy-3-sulfophenyl groups both located at position 1.	6.47	34	0	organic sodium salt	dye
valine Valine: A branched-chain essential amino acid that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway.. valine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isopropyl group.. L-valine : The L-enantiomer of valine.	2.01	1	0	L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid; valine	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
threonine Threonine: An essential amino acid occurring naturally in the L-form, which is the active form. It is found in eggs, milk, gelatin, and other proteins.. threonine : An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 1-hydroxyethyl group.	2.7	3	0	amino acid zwitterion; aspartate family amino acid; L-alpha-amino acid; proteinogenic amino acid; threonine	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
mestranol [no description available]	1.95	1	0	17beta-hydroxy steroid; aromatic ether; terminal acetylenic compound	prodrug; xenoestrogen
tryptophan Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3.	2.92	4	0	erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; tryptophan zwitterion; tryptophan	antidepressant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
arginine Arginine: An essential amino acid that is physiologically active in the L-form.. arginine : An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group.	5.13	14	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]	2.02	1	0	alkyne; gas molecular entity; terminal acetylenic compound
methylene chloride Methylene Chloride: A chlorinated hydrocarbon that has been used as an inhalation anesthetic and acts as a narcotic in high concentrations. Its primary use is as a solvent in manufacturing and food technology.. dichloromethane : A member of the class of chloromethanes that is methane in which two of the hydrogens have been replaced by chlorine. A dense, non-flammible colourless liquid at room temperature (b.p. 40degreeC, d = 1.33) which is immiscible with water, it is widely used as a solvent, a paint stripper, and for the removal of caffeine from coffee and tea.	2.46	2	0	chloromethanes; volatile organic compound	carcinogenic agent; polar aprotic solvent; refrigerant
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.	1.99	1	0	alkyl hydroperoxide	antibacterial agent; oxidising agent
bromthymol blue Bromthymol Blue: A pH sensitive dye that has been used as an indicator in many laboratory reactions.. bromothymol blue : A member of the class of 2,1-benzoxathioles that is 2,1-benzoxathiole 1,1-dioxide in which both of the hydrogens at position 3 have been substituted by 3-bromo-4-hydroxy-5-isopropyl-2-methylphenyl groups.	1.97	1	0	2,1-benzoxathiole; arenesulfonate ester; organobromine compound; polyphenol; sultone	acid-base indicator; dye; two-colour indicator
bromcresol green Bromcresol Green: An indicator and reagent. It has been used in serum albumin determinations and as a pH indicator.	2.02	1	0	benzofurans
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.	2.06	1	0	benzenes; piperidines	anaesthetic; neurotoxin; NMDA receptor antagonist; psychotropic drug
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.	1.98	1	0	chloroethenes	inhalation anaesthetic; mouse metabolite
dehydrocholic acid Dehydrocholic Acid: A semisynthetic bile acid made from cholic acid. It is used as a cholagogue, hydrocholeretic, diuretic, and as a diagnostic aid.. 3,7,12-trioxo-5beta-cholanic acid : An oxo-5beta-cholanic acid in which three oxo substituents are located at positions 3, 7 and 12 on the cholanic acid skeleton.	10.79	30	0	12-oxo steroid; 3-oxo-5beta-steroid; 7-oxo steroid; oxo-5beta-cholanic acid	gastrointestinal drug
methylprednisolone Methylprednisolone: A PREDNISOLONE derivative with similar anti-inflammatory action.. 6alpha-methylprednisolone : The 6alpha-stereoisomer of 6-methylprednisolone.	2.67	3	0	6-methylprednisolone; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	adrenergic agent; anti-inflammatory drug; antiemetic; environmental contaminant; neuroprotective agent; xenobiotic
rotenone Derris: A plant genus of the family FABACEAE. The root is a source of rotenoids (ROTENONE) and flavonoids. Some species of Pongamia have been reclassified to this genus and some to MILLETTIA. Some species of Deguelia have been reclassified to this genus.. rotenoid : Members of the class of tetrahydrochromenochromene that consists of a cis-fused tetrahydrochromeno[3,4-b]chromene skeleton and its substituted derivatives. The term was originally restricted to natural products, but is now also used to describe semi-synthetic and fully synthetic compounds.	2.41	2	0	organic heteropentacyclic compound; rotenones	antineoplastic agent; metabolite; mitochondrial NADH:ubiquinone reductase inhibitor; phytogenic insecticide; piscicide; toxin
penicillin v Penicillin V: A broad-spectrum penicillin antibiotic used orally in the treatment of mild to moderate infections by susceptible gram-positive organisms.. phenoxymethylpenicillin : A penicillin compound having a 6beta-(phenoxyacetyl)amino side-chain.	2.42	2	0	penicillin allergen; penicillin
penicillanic acid Penicillanic Acid: A building block of penicillin, devoid of significant antibacterial activity. (From Merck Index, 11th ed). penicillanic acid : A penam that consists of 3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane bearing a carboxy group at position 2 and having (2S,5R)-configuration.	2	1	0	penicillanic acids
xylitol xylooligosaccharide: structure in first source. pentitol : An alditol obtained by reduction of any pentose.. xylooligosaccharide : An oligosaccharide comprised of xylose residues.	2.08	1	0
n-vinyl-2-pyrrolidinone N-vinyl-2-pyrrolidinone: monomer of POVIDONE; structure given in first source	2.77	3	0	pyrrolidin-2-ones
beta-glucono-1,5-lactone beta-glucono-1,5-lactone: structure. D-glucono-1,5-lactone : An aldono-1,5-lactone obtained from D-gluconic acid.	2.37	2	0	aldono-1,5-lactone; gluconolactone	animal metabolite; mouse metabolite
quinoxalines quinoxaline : A naphthyridine in which the nitrogens are at positions 1 and 4.	2.31	1	0	mancude organic heterobicyclic parent; naphthyridine; ortho-fused heteroarene
xanthenes Xanthenes: Compounds with three aromatic rings in linear arrangement with an OXYGEN in the center ring.	2.4	2	0	xanthene
phenothiazine 10H-phenothiazine : The 10H-tautomer of phenothiazine.	2.41	2	0	phenothiazine	ferroptosis inhibitor; plant metabolite; radical scavenger
propylparaben Parabens: Methyl, propyl, butyl, and ethyl esters of p-hydroxybenzoic acid. They have been approved by the FDA as antimicrobial agents for foods and pharmaceuticals. (From Hawley's Condensed Chemical Dictionary, 11th ed, p872)	2.05	1	0	benzoate ester; paraben; phenols	antifungal agent; antimicrobial agent
4-nitroaniline [no description available]	1.97	1	0	nitroaniline	bacterial xenobiotic metabolite
benzylamine aminotoluene : Any member of the class of toluenes carrying one or more amino groups.	2.89	1	0	aralkylamine; primary amine	allergen; EC 3.5.5.1 (nitrilase) inhibitor; plant metabolite
pyridostigmine bromide Pyridostigmine Bromide: A cholinesterase inhibitor with a slightly longer duration of action than NEOSTIGMINE. It is used in the treatment of myasthenia gravis and to reverse the actions of muscle relaxants.	1.95	1	0	pyridinium salt
allylamine Allylamine: Possesses an unusual and selective cytotoxicity for VASCULAR SMOOTH MUSCLE cells in dogs and rats. Useful for experiments dealing with arterial injury, myocardial fibrosis or cardiac decompensation.	2.44	2	0	alkylamine
allyl alcohol allyl alcohol: structure. allylic alcohol : An alcohol where the hydroxy group is attached to a saturated carbon atom adjacent to a double bond (R groups may be H, organyl, etc.).. allyl alcohol : A propenol in which the C=C bond connects C-2 and C-3. It is has been found in garlic (Allium sativum). Formerly used as a herbicide for the control of various grass and weed seeds.	2	1	0	primary allylic alcohol; propenol	antibacterial agent; fungicide; herbicide; insecticide; plant metabolite
isethionic acid Isethionic Acid: A colorless, syrupy, strongly acidic liquid that can form detergents with oleic acid.. isethionic acid : An alkanesulfonic acid in which the sulfo group is directly linked to a 2-hydroxyethyl group.	2.39	2	0	alkanesulfonic acid	human metabolite
2-methylpentane Hexanes: Six-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Various polyneuropathies are caused by hexane poisoning.	1.96	1	0	alkane
methyl isobutyl ketone [no description available]	1.98	1	0	ketone
bromobenzene [no description available]	2	1	0	bromoarene; bromobenzenes; volatile organic compound	hepatotoxic agent; mouse metabolite; non-polar solvent
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.	2.53	2	0	pyrrole; secondary amine
thiophenes Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.	2.76	3	0	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
n-decyl alcohol n-decyl alcohol: RN given refers to parent cpd. decanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of ten carbon atoms.. decan-1-ol : A fatty alcohol consisting of a hydroxy function at C-1 of an unbranched saturated chain of ten carbon atoms.	2.01	1	0	decanol; primary alcohol	metabolite; pheromone; protic solvent
phenformin Phenformin: A biguanide hypoglycemic agent with actions and uses similar to those of METFORMIN. Although it is generally considered to be associated with an unacceptably high incidence of lactic acidosis, often fatal, it is still available in some countries. (From Martindale, The Extra Pharmacopoeia, 30th ed, p290). phenformin : A member of the class of biguanides that is biguanide in which one of the terminal nitrogen atoms is substituted by a 2-phenylethyl group. It was used as an anti-diabetic drug but was later withdrawn from the market due to potential risk of lactic acidosis.	2.69	3	0	biguanides	antineoplastic agent; geroprotector; hypoglycemic agent
bromphenol blue Bromphenol Blue: A dye that has been used as an industrial dye, a laboratory indicator, and a biological stain.. bromophenol blue : 3H-2,1-Benzoxathiole 1,1-dioxide in which both of the hydrogens at position 3 have been substituted by 3,5-dibromo-4-hydroxyphenyl groups. It is used as a laboratory indicator, changing from yellow below pH 3 to purple at pH 4.6, and as a size marker for monitoring the progress of agarose gel and polyacrylamide gel electrophoresis. It has also been used as an industrial dye.	2.37	2	0	2,1-benzoxathiole; arenesulfonate ester; organobromine compound; phenols; sultone	acid-base indicator; dye; two-colour indicator
framycetin Framycetin: A component of NEOMYCIN that is produced by Streptomyces fradiae. On hydrolysis it yields neamine and neobiosamine B. (From Merck Index, 11th ed). framycetin : A tetracyclic antibacterial agent derived from neomycin, being a glycoside ester of neamine and neobiosamine B.	2.41	2	0	aminoglycoside	allergen; antibacterial drug; Escherichia coli metabolite
vanillic acid Vanillic Acid: A flavoring agent. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13).. vanillic acid : A monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3.	2.03	1	0	methoxybenzoic acid; monohydroxybenzoic acid	plant metabolite
pyrazolanthrone pyrazolanthrone: JNK (c-Jun N-terminal kinase) inhibitor; structure in first source. anthra[1,9-cd]pyrazol-6(2H)-one : A member of the class of anthrapyrazoles that is anthra[1,9-cd]pyrazole substituted at position 6 by an oxo group. An inhibitor of c-Jun N-terminal kinase.	2.07	1	0	anthrapyrazole; aromatic ketone; cyclic ketone	antineoplastic agent; c-Jun N-terminal kinase inhibitor; geroprotector
dimethyl phthalate dimethyl phthalate: used as plasticizer in computer mouse; structure	1.96	1	0	diester; methyl ester; phthalate ester
diatrizoate meglumine Diatrizoate Meglumine: A versatile contrast medium used for DIAGNOSTIC X-RAY RADIOLOGY.. meglumine amidotrizoate : The N-methylglucamine salt of amidotrizoic acid. Both the sodium and the meglumine salts of amidotrizoic acid have been widely used as water-soluble radioopaque media in diagnostic radiography. The use of a mixture of the two salts is often preferred, as adverse effects can be reduced.	1.98	1	0	monocarboxylic acid anion	radioopaque medium
meglumine Meglumine: 1-Deoxy-1-(methylamino)-D-glucitol. A derivative of sorbitol in which the hydroxyl group in position 1 is replaced by a methylamino group. Often used in conjunction with iodinated organic compounds as contrast medium.. N-methylglucamine : A hexosamine that is D-glucitol in which the hydroxy group at position 1 is substituted by the nitrogen of a methylamino group. A crystalline base, it is used in preparing salts of certain acids for use as diagnostic radiopaque media, while its antimonate is used as an antiprotozoal in the treatment of leishmaniasis.	2.42	2	0	hexosamine; secondary amino compound
uridine diphosphate glucose Uridine Diphosphate Glucose: A key intermediate in carbohydrate metabolism. Serves as a precursor of glycogen, can be metabolized into UDPgalactose and UDPglucuronic acid which can then be incorporated into polysaccharides as galactose and glucuronic acid. Also serves as a precursor of sucrose lipopolysaccharides, and glycosphingolipids.. UDP-alpha-D-glucose : The alpha-anomer of UDP-alpha-D-glucose. It is used in nucleotide sugars metabolism.	2.01	1	0	UDP-D-glucose	fundamental 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.	2.67	3	0	naphthol	antinematodal drug; genotoxin; human urinary metabolite; human xenobiotic metabolite; mouse metabolite; radical scavenger
dextrothyroxine Dextrothyroxine: The dextrorotary isomer of the synthetic THYROXINE.. D-thyroxine : The D-enantiomer of thyroxine.	2.02	1	0	D-tyrosine derivative; thyroxine
ethyl acetate ethyl acetate : The acetate ester formed between acetic acid and ethanol.	2.36	2	0	acetate ester; ethyl ester; volatile organic compound	EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor; metabolite; polar aprotic solvent; Saccharomyces cerevisiae metabolite
sodium cyanide Sodium Cyanide: A highly poisonous compound that is an inhibitor of many metabolic processes and is used as a test reagent for the function of chemoreceptors. It is also used in many industrial processes.. sodium cyanide : A cyanide salt containing equal numbers of sodium cations and cyanide anions.	2.39	2	0	cyanide salt; one-carbon compound; sodium salt	EC 1.15.1.1 (superoxide dismutase) inhibitor
yohimbine Yohimbine: A plant alkaloid with alpha-2-adrenergic blocking activity. Yohimbine has been used as a mydriatic and in the treatment of ERECTILE DYSFUNCTION.. yohimbine : An indole alkaloid with alpha2-adrenoceptor antagonist activity. It is produced by Corynanthe johimbe and Rauwolfia serpentina.	2.05	1	0	methyl 17-hydroxy-20xi-yohimban-16-carboxylate	alpha-adrenergic antagonist; dopamine receptor D2 antagonist; serotonergic antagonist
3-o-methylglucose 3-O-Methylglucose: A non-metabolizable glucose analogue that is not phosphorylated by hexokinase. 3-O-Methylglucose is used as a marker to assess glucose transport by evaluating its uptake within various cells and organ systems. (J Neurochem 1993;60(4):1498-504). 3-O-methyl-D-glucose : A D-aldohexose that is D-glucose in which the hydrogen of the hydroxy group at position 3 has been substituted by a methyl group. It is a non-metabolisable glucose analogue that is not phosphorylated by hexokinase and is used as a marker to assess glucose transport by evaluating its uptake within various cells and organ systems.	1.97	1	0	D-aldohexose derivative
potassium cyanide [no description available]	2.05	1	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.	2.52	2	0	catechin	antioxidant; plant metabolite
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.	5.09	3	1	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinazolines
acridines Acridines: Compounds that include the structure of acridine.. acridine : A polycyclic heteroarene that is anthracene in which one of the central CH groups is replaced by a nitrogen atom.	2.92	4	0	acridines; mancude organic heterotricyclic parent; polycyclic heteroarene	genotoxin
cyclopentane Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.	2.39	2	0	cycloalkane; cyclopentanes; volatile organic compound	non-polar solvent
isoxazoles Isoxazoles: Azoles with an OXYGEN and a NITROGEN next to each other at the 1,2 positions, in contrast to OXAZOLES that have nitrogens at the 1,3 positions.. isoxazole : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing three carbon atoms and an oxygen and nitrogen atom adjacent to each other. It is the parent of the class of isoxazoles.. isoxazoles : Oxazoles in which the N and O atoms are adjacent.	5.01	12	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.	1.98	1	0	1,3-oxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
thiazoles [no description available]	3.62	9	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.	1.98	1	0	diazine; pyrazines	Daphnia magna metabolite
nitroblue tetrazolium Nitroblue Tetrazolium: Colorless to yellow dye that is reducible to blue or black formazan crystals by certain cells; formerly used to distinguish between nonbacterial and bacterial diseases, the latter causing neutrophils to reduce the dye; used to confirm diagnosis of chronic granulomatous disease.	2	1	0	organic cation
calcium gluconate [no description available]	1.97	1	0	calcium salt	nutraceutical
paraoxon [no description available]	2.01	1	0	aryl dialkyl phosphate; organophosphate insecticide	EC 3.1.1.7 (acetylcholinesterase) inhibitor; mouse metabolite
evans blue Evans Blue: An azo dye used in blood volume and cardiac output measurement by the dye dilution method. It is very soluble, strongly bound to plasma albumin, and disappears very slowly.. Evans blue : An organic sodium salt that is the tetrasodium salt of 6,6'-{(3,3'-dimethyl[1,1'-biphenyl]-4,4'-diyl)bis[diazene-2,1-diyl]}bis(4-amino-5-hydroxynaphthalene-1,3-disulfonate). It is sometimes used as a counterstain, especially in fluorescent methods to suppress background autofluorescence.	2.67	3	0	organic sodium salt	fluorochrome; histological dye; sodium channel blocker; teratogenic agent
linuron Linuron: A selective pre- and post-emergence herbicide. (From Merck Index, 11th ed). linuron : A member of the class of phenylureas that is N-methyl urea substituted by a methoxy group at position 1 and a 3,4-dichlorophenyl group at position 3.	2.03	1	0	dichlorobenzene; phenylureas	agrochemical; environmental contaminant; herbicide; xenobiotic
phenylbenzoquinone phenylbenzoquinone: RN given refers to parent cpd	1.98	1	0
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)	1.97	1	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
perflubron perflubron: potential anti-obesity compound; reduces food adsorption; 8-carbon perfluorocarbon radiopaque compound; an oral contrast agent for use with MRI to enhance delineation of the bowel distinguishing it from adjacent organs. perflubron : A haloalkane that is perfluorooctane in which a fluorine attached to one of the terminal carbons has been replaced by a bromine.	2.04	1	0	haloalkane; organobromine compound; perfluorinated compound	blood substitute; radioopaque medium
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.	5.46	65	0	bile acid; C24-steroid; monohydroxy-5beta-cholanic acid	geroprotector; human metabolite; mouse metabolite
nandrolone Nandrolone: C18 steroid with androgenic and anabolic properties. It is generally prepared from alkyl ethers of ESTRADIOL to resemble TESTOSTERONE but less one carbon at the 19 position.. nandrolone : A 3-oxo Delta(4)-steroid that is estr-4-en-3-one substituted by a beta-hydroxy group at position 17.	2.04	1	0	17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; anabolic androgenic steroid	human metabolite
4-toluenesulfonyl fluoride 4-toluenesulfonyl fluoride: inhibitor of peptide hydrolases; structure in second source	2.01	1	0
fluorobenzenes Fluorobenzenes: Derivatives of BENZENE that contain FLUORINE.. monofluorobenzene : The simplest member of the class of monofluorobenzenes that is benzene carrying a single fluoro substituent.. fluorobenzenes : Any fluoroarene that is a benzene or a substituted benzene carrying at least one fluoro group.	3.77	10	0	monofluorobenzenes	NMR chemical shift reference compound
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.	2	1	0	1-benzyl-3-(dimethylamino)-2-methyl-1-phenylpropyl propanoate	mu-opioid receptor agonist; opioid analgesic
limestone Calcium Carbonate: Carbonic acid calcium salt (CaCO3). An odorless, tasteless powder or crystal that occurs in nature. It is used therapeutically as a phosphate buffer in hemodialysis patients and as a calcium supplement.. calcium carbonate : A calcium salt with formula CCaO3.	2.66	3	0	calcium salt; carbonate salt; inorganic calcium salt; one-carbon compound	antacid; fertilizer; food colouring; food firming agent
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.	13.38	173	0	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
glycocholic acid Glycocholic Acid: The glycine conjugate of CHOLIC ACID. It acts as a detergent to solubilize fats for absorption and is itself absorbed.. glycocholic acid : A bile acid glycine conjugate having cholic acid as the bile acid component.. glycocholate : A cholanic acid conjugate anion that is the conjugate base of glycocholic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.	15.72	239	2	bile acid glycine conjugate	human metabolite
kainic acid Kainic Acid: (2S-(2 alpha,3 beta,4 beta))-2-Carboxy-4-(1-methylethenyl)-3-pyrrolidineacetic acid. Ascaricide obtained from the red alga Digenea simplex. It is a potent excitatory amino acid agonist at some types of excitatory amino acid receptors and has been used to discriminate among receptor types. Like many excitatory amino acid agonists it can cause neurotoxicity and has been used experimentally for that purpose.	1.98	1	0	dicarboxylic acid; L-proline derivative; non-proteinogenic L-alpha-amino acid; pyrrolidinecarboxylic acid	antinematodal drug; excitatory amino acid agonist
indican indoxyl sulfate : An aryl sulfate that is indoxyl in which the hydroxyl hydrogen is substituted by a sulfo group.	2.02	1	0	aryl sulfate; indoles	human metabolite
isomaltose [no description available]	2.08	1	0
dipicolinic acid dipicolinic acid : A pyridinedicarboxylic acid carrying two carboxy groups at positions 2 and 6.	2.11	1	0	pyridinedicarboxylic acid	bacterial metabolite
phorone phorone: an industrial solvent; structure	1.97	1	0	dialkenyl ketone
alpha-aminopyridine alpha-aminopyridine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #485. aminopyridine : Compounds containing a pyridine skeleton substituted by one or more amine groups.	1.96	1	0
cyanogen bromide Cyanogen Bromide: Cyanogen bromide (CNBr). A compound used in molecular biology to digest some proteins and as a coupling reagent for phosphoroamidate or pyrophosphate internucleotide bonds in DNA duplexes.	1.95	1	0
oleanolic acid [no description available]	2.03	1	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	plant metabolite
medroxyprogesterone [no description available]	2.04	1	0	17alpha-hydroxy steroid; 20-oxo steroid; 3-oxo-Delta(4) steroid; tertiary alpha-hydroxy ketone	contraceptive drug; progestin; synthetic oral contraceptive
dihydrotestosterone Dihydrotestosterone: A potent androgenic metabolite of TESTOSTERONE. It is produced by the action of the enzyme 3-OXO-5-ALPHA-STEROID 4-DEHYDROGENASE.. 17beta-hydroxyandrostan-3-one : A 17beta-hydroxy steroid that is testosterone in which the 4-5 double bond has been reduced to a single bond with unspecified configuration at position 5.. 17beta-hydroxy-5alpha-androstan-3-one : A 17beta-hydroxy steroid that is testosterone in which the 4,5 double bond has been reduced to a single bond with alpha-configuration at position 5.	2.7	3	0	17beta-hydroxy steroid; 17beta-hydroxyandrostan-3-one; 3-oxo-5alpha-steroid	androgen; Daphnia magna metabolite; human metabolite; mouse metabolite
copper gluconate Gluconates: Derivatives of gluconic acid (the structural formula HOCH2(CHOH)4COOH), including its salts and esters.	2.37	2	0	organic molecular entity
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.	4.6	25	0	dialdehyde	biomarker
trinitrobenzenesulfonic acid Trinitrobenzenesulfonic Acid: A reagent that is used to neutralize peptide terminal amino groups.. 2,4,6-trinitrobenzenesulfonic acid : The arenesulfonic acid that is benzenesulfonic acid with three nitro substituents in the 2-, 4- and 6-positions.	2.13	1	0	arenesulfonic acid; C-nitro compound	epitope; explosive; reagent
eosine yellowish-(ys) Eosine Yellowish-(YS): A versatile red dye used in cosmetics, pharmaceuticals, textiles, etc., and as tissue stain, vital stain, and counterstain with HEMATOXYLIN. It is also used in special culture media.. eosin YS dye : An organic sodium salt that is 2',4',5',7'-tetrabromofluorescein in which the carboxy group and the phenolic hydroxy group have been deprotonated and the resulting charge is neutralised by two sodium ions.	1.95	1	0	organic sodium salt; organobromine compound	fluorochrome; histological dye
gentian violet Gentian Violet: A dye that is a mixture of violet rosanilinis with antibacterial, antifungal, and anthelmintic properties.. crystal violet : An organic chloride salt that is the monochloride salt of crystal violet cation. It has been used in creams for the topical treatment of bacterial and fungal infections, being effective against some Gram-positive bacteria (notably Staphylococcus species) and some pathogenic fungi (including Candida species) but use declined following reports of animal carcinogenicity. It has also been used for dying wood, silk, and paper, as well as a histological stain.	2.73	3	0	organic chloride salt	anthelminthic drug; antibacterial agent; antifungal agent; antiseptic drug; histological dye
1-naphthylisothiocyanate 1-Naphthylisothiocyanate: A tool for the study of liver damage which causes bile stasis and hyperbilirubinemia acutely and bile duct hyperplasia and biliary cirrhosis chronically, with changes in hepatocyte function. It may cause skin and kidney damage.	3.37	7	0	isothiocyanate	insecticide
aminopenicillanic acid aminopenicillanic acid: RN given refers to parent cpd; structure. 6-aminopenicillanic acid : A penicillanic acid compound having a (6R)-amino substituent. The active nucleus common to all penicillins, it may be substituted at the 6-amino position to form the semisynthetic penicillins, resulting in a variety of antibacterial and pharmacologic characteristics.	2	1	0	amino acid zwitterion; penicillanic acids	allergen
4-chloromercuribenzenesulfonate 4-Chloromercuribenzenesulfonate: A cytotoxic sulfhydryl reagent that inhibits several subcellular metabolic systems and is used as a tool in cellular physiology.	2.36	2	0	arenesulfonic acid; arylmercury compound
tripalmitin tripalmitin: structure. tripalmitin : A triglyceride obtained by formal acylation of the three hydroxy groups of glycerol by palmitic (hexadecanoic) acid.	2.08	1	0	triglyceride
glycerylphosphorylcholine Glycerylphosphorylcholine: A component of PHOSPHATIDYLCHOLINES or LECITHINS, in which the two hydroxy groups of GLYCEROL are esterified with fatty acids. (From Stedman, 26th ed)	2.36	2	0	glycerophosphocholine
congo red Congo Red: An acid dye used in testing for hydrochloric acid in gastric contents. It is also used histologically to test for AMYLOIDOSIS.. Congo Red : An indicator dye that is blue-violet at pH 3.0 and red at pH 5.0.	2.07	1	0	bis(azo) compound
lactulose [no description available]	2.06	1	0	glycosylfructose	gastrointestinal drug; laxative
docusate Dioctyl Sulfosuccinic Acid: All-purpose surfactant, wetting agent, and solubilizer used in the drug, cosmetics, and food industries. It has also been used in laxatives and as cerumenolytics. It is usually administered as either the calcium, potassium, or sodium salt.	2.03	1	0	diester; organosulfonic acid
methyl n-butyl ketone Methyl n-Butyl Ketone: An industrial solvent which causes nervous system degeneration. MBK is an acronym often used to refer to it.. hexanone : A ketone that is a hexane carrying an oxo substituent at unspecified position.	1.98	1	0	ketone
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	3.78	11	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
ethyl pyruvate [no description available]	2.76	3	0	oxo carboxylic acid
Berberine chloride (TN) [no description available]	3.15	1	0	organic molecular entity
glycochenodeoxycholic acid Glycochenodeoxycholic Acid: A bile salt formed in the liver from chenodeoxycholate and glycine, usually as the sodium salt. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is a cholagogue and choleretic.. glycochenodeoxycholate : A N-acylglycinate that is the conjugate base of glycochenodeoxycholic acid.. glycochenodeoxycholic acid : A bile acid glycine conjugate having 3alpha,7alpha-dihydroxy-5beta-cholan-24-oyl as the bile acid component.	6.61	50	1	bile acid glycine conjugate	human metabolite
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.	3.9	12	0	cyclic ketone; erythromycin
dehydroepiandrosterone sulfate Dehydroepiandrosterone Sulfate: The circulating form of a major C19 steroid produced primarily by the ADRENAL CORTEX. DHEA sulfate serves as a precursor for TESTOSTERONE; ANDROSTENEDIONE; ESTRADIOL; and ESTRONE.. dehydroepiandrosterone sulfate : A steroid sulfate that is the 3-sulfooxy derivative of dehydroepiandrosterone.	5.46	20	0	17-oxo steroid; steroid sulfate	EC 2.7.1.33 (pantothenate kinase) inhibitor; human metabolite; mouse metabolite
nitrosoguanidines Nitrosoguanidines: Nitrosylated derivatives of guanidine. They are used as MUTAGENS in MOLECULAR BIOLOGY research.	1.95	1	0
methylnitrosourea Methylnitrosourea: A nitrosourea compound with alkylating, carcinogenic, and mutagenic properties.. N-methyl-N-nitrosourea : A member of the class of N-nitrosoureas that is urea in which one of the nitrogens is substituted by methyl and nitroso groups.	1.95	1	0	N-nitrosoureas	alkylating agent; carcinogenic agent; mutagen; teratogenic agent
4-nitrophenyl acetate [no description available]	2.66	3	0	C-nitro compound; phenyl acetates
vinblastine [no description available]	4.05	4	0
1-methylpyridinium 1-methylpyridinium: RN given refers to parent cpd	3.57	2	0	methylpyridines
deoxycytidine [no description available]	2.11	1	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
rhodamine 6g rhodamine 6G: RN given refers to HCl	2.02	1	0
allylglycine Allylglycine: An inhibitor of glutamate decarboxylase and an antagonist of GAMMA-AMINOBUTYRIC ACID. It is used to induce convulsions in experimental animals.	1.99	1	0
phenylglyoxal [no description available]	2	1	0	phenylacetaldehydes
dehydroepiandrosterone acetate 3beta-acetoxyandrost-5-en-17-one: structure in first source	2	1	0	steroid ester
ethidium bromide [no description available]	2.73	3	0	organic bromide salt	geroprotector; intercalator; trypanocidal drug
durapatite Durapatite: The mineral component of bones and teeth; it has been used therapeutically as a prosthetic aid and in the prevention and treatment of osteoporosis.. hydroxylapatite : A phosphate mineral with the formula Ca5(PO4)3(OH).	2.67	3	0
sodium hydroxide Sodium Hydroxide: A highly caustic substance that is used to neutralize acids and make sodium salts. (From Merck Index, 11th ed)	2.88	4	0	alkali metal hydroxide
sorbitan monostearate sorbitan monostearate: Stearic Acid was the HM (74-82), no longer an active MH	2.25	1	0
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.	2.93	4	0	glycopeptide	antibacterial drug; antimicrobial agent; bacterial metabolite
glycyrrhizic acid glycyrrhizinic acid : A triterpenoid saponin that is the glucosiduronide derivative of 3beta-hydroxy-11-oxoolean-12-en-30-oic acid.	2.78	3	0	enone; glucosiduronic acid; pentacyclic triterpenoid; tricarboxylic acid; triterpenoid saponin	EC 3.4.21.5 (thrombin) inhibitor; plant metabolite
d-alpha tocopherol Vitamin E: A generic descriptor for all TOCOPHEROLS and TOCOTRIENOLS that exhibit ALPHA-TOCOPHEROL activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of ISOPRENOIDS.. tocopherol : A collective name for a group of closely related lipids that contain a chroman-6-ol nucleus substituted at position 2 by a methyl group and by a saturated hydrocarbon chain consisting of three isoprenoid units. They are designated as alpha-, beta-, gamma-, and delta-tocopherol depending on the number and position of additional methyl substituents on the aromatic ring. Tocopherols occur in vegetable oils and vegetable oil products, almost exclusively with R,R,R configuration. Tocotrienols differ from tocopherols only in having three double bonds in the hydrocarbon chain.. vitamin E : Any member of a group of fat-soluble chromanols that exhibit biological activity against vitamin E deficiency. The vitamers in this class consists of a chroman-6-ol core which is substituted at position 2 by a methyl group and (also at position 2) either a saturated or a triply-unsaturated hydrocarbon chain consisting of three isoprenoid units. The major function of vitamin E is to act as a natural antioxidant by scavenging free radicals and molecular oxygen.. (R,R,R)-alpha-tocopherol : An alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils.	3.99	14	0	alpha-tocopherol	algal metabolite; antiatherogenic agent; anticoagulant; antioxidant; antiviral agent; EC 2.7.11.13 (protein kinase C) inhibitor; immunomodulator; micronutrient; nutraceutical; plant metabolite
tocopherols [no description available]	2.67	3	0
pregnenolone carbonitrile Pregnenolone Carbonitrile: A catatoxic steroid and microsomal enzyme inducer having significant effects on the induction of cytochrome P450. It has also demonstrated the potential for protective capability against acetaminophen-induced liver damage.	2.64	3	0	aliphatic nitrile
digoxigenin Digoxigenin: 3 beta,12 beta,14-Trihydroxy-5 beta-card-20(22)-enolide. A cardenolide which is the aglycon of digoxin. Can be obtained by hydrolysis of digoxin or from Digitalis orientalis L. and Digitalis lanata Ehrh.. digoxigenin : A hydroxy steroid that consists of 5beta-cardanolide having a double bond at the 20(22)-position as well as hydroxy groups at the 3beta-, 12beta- and 14beta-positions. It has been isolated from the plant species of the genus Digitalis.	1.99	1	0	12beta-hydroxy steroid; 14beta-hydroxy steroid; 3beta-hydroxy steroid; 3beta-sterol	hapten; plant metabolite
stearylamine stearylamine: RN given refers to parent cpd. octadecan-1-amine : An 18-carbon primary aliphatic amine.	2.03	1	0	primary aliphatic amine	film-forming compound
5 alpha-androstane-3 alpha,17 beta-diol 5alpha-androstane-3alpha,17beta-diol : The 5alpha-stereoisomer of androstane-3alpha,17beta-diol.	2.04	1	0	androstane-3alpha,17beta-diol	Daphnia magna metabolite; human metabolite
ethyldimethylaminopropyl carbodiimide Ethyldimethylaminopropyl Carbodiimide: Carbodiimide cross-linking reagent.	1.98	1	0
methionine sulfoximine methionine sulfoximine : A non-proteinogenic alpha-amino acid that is the sulfoximine derivative of methionine .	2.89	1	0	methionine derivative; non-proteinogenic alpha-amino acid; sulfoximide
amiloride Amiloride: A pyrazine compound inhibiting SODIUM reabsorption through SODIUM CHANNELS in renal EPITHELIAL CELLS. This inhibition creates a negative potential in the luminal membranes of principal cells, located in the distal convoluted tubule and collecting duct. Negative potential reduces secretion of potassium and hydrogen ions. Amiloride is used in conjunction with DIURETICS to spare POTASSIUM loss. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p705). amiloride : A member of the class of pyrazines resulting from the formal monoacylation of guanidine with the carboxy group of 3,5-diamino-6-chloropyrazine-2-carboxylic acid.	5.23	16	0	aromatic amine; guanidines; organochlorine compound; pyrazines	diuretic; sodium channel blocker
azetidyl-2-carboxylic acid azetidyl-2-carboxylic acid: a proline analog (with 4-membered ring in place of 5); a toxic non-protein amino acid that is misincorporated into protein in place of proline; induces nonfunctional heat-shock proteins; inhibits acquired thermotolerance; RN given refers to (L)-isomer; found in beets and Liliaceae. (S)-azetidine-2-carboxylic acid : The (S)-enantiomer of azetidine-2-carboxylic acid.. azetidinecarboxylic acid : A member of the class of azetidines that is azetidine substituted by at least one carboxy group at unspecified position.	2.02	1	0	azetidine-2-carboxylic acid
betamethasone valerate Betamethasone Valerate: The 17-valerate derivative of BETAMETHASONE. It has substantial topical anti-inflammatory activity and relatively low systemic anti-inflammatory activity.. betamethasone valerate : A steroid ester that is betamethasone in which the hydroxy group at the 17alpha position has been converted to the corresponding pentanoate ester.	2.04	1	0	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; fluorinated steroid; primary alpha-hydroxy ketone; steroid ester	anti-inflammatory drug
guanoxan guanoxan: was MH 1976-92 (see under GUANIDINES 1976-90); use GUANIDINES to search GUANOXAN 1976-92; antihypertensive agent similar in its mechanism of action to guanethidine; may cause liver damage	2.06	1	0	benzodioxine
phenethyl isothiocyanate phenethyl isothiocyanate: a dietary liver aldehyde dehydrogenase inhibitor; promotes urinary bladder carcinoma. phenethyl isothiocyanate : An isothiocyanate having a phenethyl group attached to the nitrogen. It is a naturally occurring compound found in some cruciferous vegetables (e.g. watercress) and is known to possess anticancer properties.	2.46	2	0	isothiocyanate	antineoplastic agent; EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor; metabolite
fluorescein Fluorescein: A phthalic indicator dye that appears yellow-green in normal tear film and bright green in a more alkaline medium such as the aqueous humor.. fluorescein (lactone form) : A xanthene dye that is highly fluorescent, detectable even when present in minute quantities. Used forensically to detect traces of blood, in analytical chemistry as an indicator in silver nitrate titrations and in microscopy.	2.92	4	0	2-benzofurans; gamma-lactone; organic heteropentacyclic compound; oxaspiro compound; polyphenol; xanthene dye	fluorescent dye; radioopaque medium
mirex Mirex: An organochlorine insecticide that is carcinogenic.	2.88	4	0	chlorocarbon; organochlorine insecticide	persistent organic pollutant
fucose Fucose: A six-member ring deoxysugar with the chemical formula C6H12O5. It lacks a hydroxyl group on the carbon at position 6 of the molecule.. L-fucopyranose : The pyranose form of L-fucose.. fucose : Any deoxygalactose that is deoxygenated at the 6-position.	2.38	2	0	fucopyranose; L-fucose	Escherichia coli metabolite; mouse metabolite
c.i. direct blue 1 [no description available]	3.51	1	0
uridine diphosphate glucuronic acid Uridine Diphosphate Glucuronic Acid: A nucleoside diphosphate sugar which serves as a source of glucuronic acid for polysaccharide biosynthesis. It may also be epimerized to UDP iduronic acid, which donates iduronic acid to polysaccharides. In animals, UDP glucuronic acid is used for formation of many glucosiduronides with various aglycones.. UDP-alpha-D-glucuronic acid : A UDP-sugar having alpha-D-glucuronic acid as the sugar component.	2.03	1	0	UDP-D-glucuronic acid	Escherichia coli metabolite; human metabolite; mouse metabolite
ioglycamic acid Ioglycamic Acid: A radiopaque medium. It is a mixture of its meglumine and sodium salts and is used to visualize the biliary tract.	3.05	5	0	amidobenzoic acid
fluorescein-5-isothiocyanate Fluorescein-5-isothiocyanate: Fluorescent probe capable of being conjugated to tissue and proteins. It is used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.. fluorescein 5-isothiocyanate : The 5-isomer of fluorescein isothiocyanate. Acts as a fluorescent probe capable of being conjugated to tissue and proteins; used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.	3.72	10	0	fluorescein isothiocyanate
sabinene sabinene: RN given refers to cpd without isomeric designation. sabinene : A thujene that is a bicyclic monoterpene isolated from the essential oils of various plant species.	1.95	1	0	thujene	plant metabolite
mannose mannopyranose : The pyranose form of mannose.	2.86	4	0	D-aldohexose; D-mannose; mannopyranose	metabolite
dithiothreitol 1,4-dimercaptobutane-2,3-diol : A glycol that is butane-2,3-diol in which a hydrogen from each of the methyl groups is replaced by a thiol group.. 1,4-dithiothreitol : The threo-diastereomer of 1,4-dimercaptobutane-2,3-diol.	3.23	6	0	1,4-dimercaptobutane-2,3-diol; butanediols; dithiol; glycol; thiol	chelator; human metabolite; reducing agent
nafenopin Nafenopin: A peroxisome proliferator that is used experimentally to promote liver tumors. It has been used as an antihyperlipoproteinemic agent.. nafenopin : A racemate comprising equimolar amounts of (R)- and (S)-nafenopin. It is a peroxisome proliferator that is used experimentally to promote liver tumors. It has been used as an hypolipidemic agent.. 2-methyl-2-[4-(1,2,3,4-tetrahydronaphthalen-1-yl)phenoxy]propanoic acid : A monocarboxylic acid that is 2-hydroxy-2-methylpropanoic acid in which ther tertiary hydroxy group has been converted into the corresponding p-(1,2,3,4-tetrahydronaphthalen-1-yl)phenyl ether.	1.95	1	0	aromatic ether; monocarboxylic acid
streptomycin [no description available]	2.01	1	0	antibiotic antifungal drug; antibiotic fungicide; streptomycins	antibacterial drug; antifungal agrochemical; antimicrobial agent; antimicrobial drug; bacterial metabolite; protein synthesis inhibitor
carbonates Carbonates: Salts or ions of the theoretical carbonic acid, containing the radical CO2(3-). Carbonates are readily decomposed by acids. The carbonates of the alkali metals are water-soluble; all others are insoluble. (From Grant & Hackh's Chemical Dictionary, 5th ed). carbonates : Organooxygen compounds that are salts or esters of carbonic acid, H2CO3.	2.07	1	0	carbon oxoanion
dexpropranolol [no description available]	2	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.	2.89	1	0	diastereoisomeric mixture; homocysteines; non-proteinogenic alpha-amino acid; sulfoximide	EC 6.3.2.2 (glutamate--cysteine ligase) inhibitor; ferroptosis inducer
floxacillin Floxacillin: Antibiotic analog of CLOXACILLIN.. flucloxacillin : A penicillin compound having a 6beta-[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-carboxamido] side-chain.	2.04	1	0	penicillin allergen; penicillin	antibacterial drug
olsalazine olsalazine: cpd with 2 salicylate molecules linked together by an azo bond. olsalazine : An azobenzene that consists of two molecules of 4-aminosalicylic acid joined by an azo linkage. A prodrug for mesalazine, an anti-inflammatory drug, it is used (as the disodium salt) in the treatment of inflammatory bowel disease.	4.07	3	1	azobenzenes; dicarboxylic acid	non-steroidal anti-inflammatory drug; prodrug
n-methylaspartate N-Methylaspartate: An amino acid that, as the D-isomer, is the defining agonist for the NMDA receptor subtype of glutamate receptors (RECEPTORS, NMDA).. N-methyl-D-aspartic acid : An aspartic acid derivative having an N-methyl substituent and D-configuration.	1.98	1	0	amino dicarboxylic acid; D-alpha-amino acid; D-aspartic acid derivative; secondary amino compound	neurotransmitter agent
tiadenol tiadenol: structure	1.95	1	0	aliphatic sulfide
lanthanum [no description available]	2.04	1	0	f-block element atom; lanthanoid atom; scandium group element atom
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.	3.46	8	0	elemental manganese; manganese group element atom	Escherichia coli metabolite; micronutrient
mercury Mercury: A silver metallic element that exists as a liquid at room temperature. It has the atomic symbol Hg (from hydrargyrum, liquid silver), atomic number 80, and atomic weight 200.59. Mercury is used in many industrial applications and its salts have been employed therapeutically as purgatives, antisyphilitics, disinfectants, and astringents. It can be absorbed through the skin and mucous membranes which leads to MERCURY POISONING. Because of its toxicity, the clinical use of mercury and mercurials is diminishing.. mercury(0) : Elemental mercury of oxidation state zero.	2.66	3	0	elemental mercury; zinc group element atom	neurotoxin
praseodymium Praseodymium: An element of the rare earth family of metals. It has the atomic symbol Pr, atomic number 59, and atomic weight 140.91.	1.95	1	0	f-block element atom; lanthanoid atom
silver Silver: An element with the atomic symbol Ag, atomic number 47, and atomic weight 107.87. It is a soft metal that is used medically in surgical instruments, dental prostheses, and alloys. Long-continued use of silver salts can lead to a form of poisoning known as ARGYRIA.	1.98	1	0	copper group element atom; elemental silver	Escherichia coli metabolite
technetium Technetium: The first artificially produced element and a radioactive fission product of URANIUM. Technetium has the atomic symbol Tc, and atomic number 43. All technetium isotopes are radioactive. Technetium 99m (m=metastable) which is the decay product of Molybdenum 99, has a half-life of about 6 hours and is used diagnostically as a radioactive imaging agent. Technetium 99 which is a decay product of technetium 99m, has a half-life of 210,000 years.	3.23	6	0	manganese group element atom
terbium Terbium: An element of the rare earth family of metals. It has the atomic symbol Tb, atomic number 65, and atomic weight 158.92.	2.06	1	0	f-block element atom; lanthanoid atom
cadmium Cadmium: An element with atomic symbol Cd, atomic number 48, and atomic weight 112.41. It is a metal and ingestion will lead to CADMIUM POISONING.. elemental cadmium : An element in the zinc group of the periodic table with atomic number 48, atomic mass 112, M.P. 321degreeC, and B.P. 765degreeC). An odourless, tasteless, and highly poisonous soft, ductile, lustrous metal with electropositive properties. It has eight stable isotopes: (106)Cd, (108)Cd,(110)Cd, (111)Cd, (112)Cd, (113)Cd, (114)Cd and (116)Cd, with (112)Cd and (114)Cd being the most common.	2.67	3	0	cadmium molecular entity; zinc group element atom
cerium Cerium: An element of the rare earth family of metals. It has the atomic symbol Ce, atomic number 58, and atomic weight 140.12. Cerium is a malleable metal used in industrial applications.	2	1	0	f-block element atom; lanthanoid atom
chromium Chromium: A trace element that plays a role in glucose metabolism. It has the atomic symbol Cr, atomic number 24, and atomic weight 52. According to the Fourth Annual Report on Carcinogens (NTP85-002,1985), chromium and some of its compounds have been listed as known carcinogens.. chromium ion : An chromium atom having a net electric charge.. chromium atom : A chromium group element atom that has atomic number 24.	2.67	3	0	chromium group element atom; metal allergen	micronutrient
gadolinium Gadolinium: An element of the rare earth family of metals. It has the atomic symbol Gd, atomic number 64, and atomic weight 157.25. Its oxide is used in the control rods of some nuclear reactors.	2.42	2	0	f-block element atom; lanthanoid atom
gold Gold: A yellow metallic element with the atomic symbol Au, atomic number 79, and atomic weight 197. It is used in jewelry, goldplating of other metals, as currency, and in dental restoration. Many of its clinical applications, such as ANTIRHEUMATIC AGENTS, are in the form of its salts.	2.15	1	0	copper group element atom; elemental gold
vanadium Vanadium: A metallic element with the atomic symbol V, atomic number 23, and atomic weight 50.94. It is used in the manufacture of vanadium steel. Prolonged exposure can lead to chronic intoxication caused by absorption usually via the lungs.	1.96	1	0	elemental vanadium; vanadium group element atom	micronutrient
zalcitabine Zalcitabine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. 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 at low concentrations, acting as a chain-terminator of viral DNA by binding to reverse transcriptase. Its principal toxic side effect is axonal degeneration resulting in peripheral neuropathy.. zalcitabine : A pyrimidine 2',3'-dideoxyribonucleoside compound having cytosine as the nucleobase.	3.15	1	0	pyrimidine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; HIV-1 reverse transcriptase inhibitor
magnesium sulfate Magnesium Sulfate: A small colorless crystal used as an anticonvulsant, a cathartic, and an electrolyte replenisher in the treatment of pre-eclampsia and eclampsia. It causes direct inhibition of action potentials in myometrial muscle cells. Excitation and contraction are uncoupled, which decreases the frequency and force of contractions. (From AMA Drug Evaluations Annual, 1992, p1083). magnesium sulfate : A magnesium salt having sulfate as the counterion.	1.95	1	0	magnesium salt; metal sulfate; organic magnesium salt	anaesthetic; analgesic; anti-arrhythmia drug; anticonvulsant; calcium channel blocker; cardiovascular drug; fertilizer; tocolytic agent
acetylglucosamine Acetylglucosamine: The N-acetyl derivative of glucosamine.. N-acetyl-beta-D-glucosamine : An N-acetyl-D-glucosamine having beta-configuration at the anomeric centre.	2.38	2	0	N-acetyl-D-glucosamine	epitope
galactosamine 2-amino-2-deoxy-D-galactopyranose : The pyranose form of D-galactosamine.. D-galactosamine : The D-stereoisomer of galactosamine.	1.95	1	0	D-galactosamine; primary amino compound	toxin
dichloroacetylene [no description available]	2.02	1	0	organochlorine compound
phosphoric acid, trisodium salt [no description available]	2.11	1	0	sodium phosphate
hypochlorous acid Hypochlorous Acid: An oxyacid of chlorine (HClO) containing monovalent chlorine that acts as an oxidizing or reducing agent.. hypochlorous acid : A chlorine oxoacid with formula HOCl; a weak, unstable acid, it is the active form of chlorine in water.	2.06	1	0	chlorine oxoacid; reactive oxygen species	EC 2.5.1.18 (glutathione transferase) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; human metabolite
camptothecin NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source	2.44	2	0	delta-lactone; pyranoindolizinoquinoline; quinoline alkaloid; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor; genotoxin; plant metabolite
ferrous sulfate ferrous sulfate: Ferro-Gradumet is ferrous sulfate in controlled release form; RN given refers to Fe(+2)[1:1] salt. iron(2+) sulfate (anhydrous) : A compound of iron and sulfate in which the ratio of iron(2+) to sulfate ions is 1:1. Various hydrates occur naturally - most commonly the heptahydrate, which loses water to form the tetrahydrate at 57degreeC and the monohydrate at 65degreeC.	1.98	1	0	iron molecular entity; metal sulfate	reducing agent
barium sulfate Barium Sulfate: A compound used as an x-ray contrast medium that occurs in nature as the mineral barite. It is also used in various manufacturing applications and mixed into heavy concrete to serve as a radiation shield.. barium sulfate : A metal sulfate with formula BaO4S. Virtually insoluble in water at room temperature, it is mostly used as a component in oil well drilling fluid it occurs naturally as the mineral barite.	1.99	1	0	barium salt; inorganic barium salt; metal sulfate	radioopaque medium
monoethylglycinexylidide monoethylglycinexylidide: RN given refers to unlabeled parent cpd; metabolite of xylocaine; structure. monoethylglycinexylidide : Amino acid amide formed from 2,6-dimethylaniline and N-ethylglycine components; an active metabolite of lidocaine, formed by oxidative deethylation. Used as an indicator of hepatic function.	1.98	1	0	amino acid amide	drug metabolite
zinc sulfate Zinc Sulfate: A compound given in the treatment of conditions associated with zinc deficiency such as acrodermatitis enteropathica. Externally, zinc sulfate is used as an astringent in lotions and eye drops. (Reynolds JEF(Ed): Martindale: The Extra Pharmacopoeia (electronic version). Micromedex, Inc, Englewood, CO, 1995). zinc sulfate : A metal sulfate compound having zinc(2+) as the counterion.	1.99	1	0	metal sulfate; zinc molecular entity	fertilizer
calcium phosphate, dibasic, anhydrous calcium phosphate, dibasic, anhydrous: molecular formula CaHPO(4), DCPA=dicalcium phosphate anhydrous; don't confuse with dichloropropionanilide which also is called DCPA; MW=136.06; has greater surface area and lower pH than DCPD (dicalcium phosphate dihydrate); occurs in nature as monetite; an intermediate in preparing hydroxyapatite	2.38	2	0	calcium phosphate
calcium phosphate, monobasic, anhydrous calcium phosphate, monobasic: MW 234.05	2.38	2	0	calcium phosphate	fertilizer
tricalcium phosphate tricalcium phosphate: a form of tricalcium phosphate used as bioceramic bone replacement material; see also records for alpha-tricalcium phosphate, beta-tricalcium phosphate, calcium phosphate; apatitic tricalcium phosphate Ca9(HPO4)(PO4)5(OH) is the calcium orthophosphate leading to beta tricalcium phosphate Ca3(PO4)2 (b-TCP). calcium phosphate : A calcium salt composed of calcium and phosphate/diphosphate ions; present in milk and used for the mineralisation of calcified tissues.	2.38	2	0	calcium phosphate
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	2.39	2	0	dihydrogen
chlorine Chlorine: An element with atomic symbol Cl, atomic number 17, and atomic weight 35, and member of the halogen family.	2.36	2	0	diatomic chlorine; gas molecular entity	bleaching agent
galactose aldohexose : A hexose with a (potential) aldehyde group at one end.	2.92	4	0
poloxalene Poloxalene: A copolymer of polyethylene and polypropylene ether glycol. It is a non-ionic polyol surface-active agent used medically as a fecal softener and in cattle for prevention of bloat.. pluronic : A triblock copolymer composed of a central hydrophobic chain of poly(propylene oxide) flanked by two hydrophilic chains of poly(ethylene oxide).	2.82	3	0	epoxide
ozone Ozone: The unstable triatomic form of oxygen, O3. It is a powerful oxidant that is produced for various chemical and industrial uses. Its production is also catalyzed in the ATMOSPHERE by ULTRAVIOLET RAY irradiation of oxygen or other ozone precursors such as VOLATILE ORGANIC COMPOUNDS and NITROGEN OXIDES. About 90% of the ozone in the atmosphere exists in the stratosphere (STRATOSPHERIC OZONE).. ozone : An elemental molecule with formula O3. An explosive, pale blue gas (b.p. -112degreeC) that has a characteristic, pungent odour, it is continuously produced in the upper atmosphere by the action of solar ultraviolet radiation on atmospheric oxygen. It is an antimicrobial agent used in the production of bottled water, as well as in the treatment of meat, poultry and other foodstuffs.	2.06	1	0	elemental molecule; gas molecular entity; reactive oxygen species; triatomic oxygen	antiseptic drug; disinfectant; electrophilic reagent; greenhouse gas; mutagen; oxidising agent; tracer
tellurous acid tellurous acid: tellurite anion inhibits oxidation of NAD-linked substrates in kidney & liver mitochondria; RN given refers to parent cpd	2.63	3	0	tellurium oxoacid
4-chloro-7-nitrobenzofurazan 4-Chloro-7-nitrobenzofurazan: A benzofuran derivative used as a protein reagent since the terminal N-NBD-protein conjugate possesses interesting fluorescence and spectral properties. It has also been used as a covalent inhibitor of both beef heart mitochondrial ATPase and bacterial ATPase.. 4-chloro-7-nitrobenzofurazan : A benzoxadiazole that is 2,1,3-benzoxadiazole which is substituted at position 4 by chlorine and at position 7 by a nitro group.	2.67	3	0	benzoxadiazole; C-nitro compound; organochlorine compound	EC 1.4.3.4 (monoamine oxidase) inhibitor; EC 3.6.1.3 (adenosinetriphosphatase) inhibitor; fluorescent probe; fluorochrome
barium chloride barium chloride: RN given refers to parent cpd. barium chloride : The inorganic dichloride salt of barium.	2.01	1	0	barium salt; inorganic chloride	potassium channel blocker
clodronic acid Clodronic Acid: A diphosphonate which affects calcium metabolism. It inhibits bone resorption and soft tissue calcification.. clodronic acid : An organochlorine compound that is methylene chloride in which both hydrogens are replaced by phosphonic acid groups. It inhibits bone resorption and soft tissue calcification, and is used (often as the disodium salt tetrahydrate) as an adjunct in the treatment of severe hypercalcaemia associated with malignancy, and in the management of osteolytic lesions and bone pain associated with skeletal metastases.	2.73	3	0	1,1-bis(phosphonic acid); one-carbon compound; organochlorine compound	antineoplastic agent; bone density conservation agent
chloramine [no description available]	2	1	0	halide
ammonium bromide ammonium bromide : An ammonium salt composed of ammonium and bromide ions in a 1:1 ratio.	2.01	1	0	ammonium salt; bromide salt	NMR chemical shift reference compound
ammonium chloride Ammonium Chloride: An acidifying agent that has expectorant and diuretic effects. Also used in etching and batteries and as a flux in electroplating.. ammonium chloride : An inorganic chloride having ammonium as the counterion.	1.95	1	0	ammonium salt; inorganic chloride	ferroptosis inhibitor
ethionine L-ethionine : An S-ethylhomocysteine that has S-configuration at the chiral centre.	2.68	3	0	S-ethylhomocysteine	antimetabolite; carcinogenic agent
cysteic acid Cysteic Acid: Beta-Sulfoalanine. An amino acid with a C-terminal sulfonic acid group which has been isolated from human hair oxidized with permanganate. It occurs normally in the outer part of the sheep's fleece, where the wool is exposed to light and weather.. cysteic acid : An amino sulfonic acid that is the sulfonic acid analogue of cysteine.	3.41	1	1	alanine derivative; amino sulfonic acid; carboxyalkanesulfonic acid; cysteine derivative; non-proteinogenic alpha-amino acid	animal metabolite
thiamphenicol [no description available]	2.53	2	0	monocarboxylic acid amide; sulfone	antimicrobial agent; immunosuppressive agent
cephalexin Cephalexin: A semisynthetic cephalosporin antibiotic with antimicrobial activity similar to that of CEPHALORIDINE or CEPHALOTHIN, but somewhat less potent. It is effective against both gram-positive and gram-negative organisms.. cephalexin : A semisynthetic first-generation cephalosporin antibiotic having methyl and beta-(2R)-2-amino-2-phenylacetamido groups at the 3- and 7- of the cephem skeleton, respectively. It is effective against both Gram-negative and Gram-positive organisms, and is used for treatment of infections of the skin, respiratory tract and urinary tract.	3.56	2	0	beta-lactam antibiotic allergen; cephalosporin; semisynthetic derivative	antibacterial drug
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.	3.78	11	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
fluorides [no description available]	2.39	2	0	halide anion; monoatomic fluorine
danazol Danazol: A synthetic steroid with antigonadotropic and anti-estrogenic activities that acts as an anterior pituitary suppressant by inhibiting the pituitary output of gonadotropins. It possesses some androgenic properties. Danazol has been used in the treatment of endometriosis and some benign breast disorders.	2.7	3	0	17beta-hydroxy steroid; terminal acetylenic compound	anti-estrogen; estrogen antagonist; geroprotector
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.	3.5	8	0	aminoglycoside antibiotic; anthracycline; p-quinones; tetracenequinones	antineoplastic agent; bacterial metabolite
carbimazole Carbimazole: An imidazole antithyroid agent. Carbimazole is metabolized to METHIMAZOLE, which is responsible for the antithyroid activity.. carbimazole : A member of the class of imidazoles that is methimazole in which the nitrogen bearing a hydrogen is converted into its ethoxycarbonyl derivative. A prodrug for methimazol, carbimazole is used for the treatment of hyperthyroidism.	1.98	1	0	1,3-dihydroimidazole-2-thiones; carbamate ester	antithyroid drug; prodrug
bromocriptine Bromocriptine: A semisynthetic ergotamine alkaloid that is a dopamine D2 agonist. It suppresses prolactin secretion.	2.39	2	0	indole alkaloid	antidyskinesia agent; antiparkinson drug; dopamine agonist; hormone antagonist
ergocristine ergocristine: an ergot alkaloid; one of the three components of ergotoxine; has alpha blocking action, stimulates smooth muscles & antagonizes serotonin; used as oxytocic & in peripheral disorders; minor descriptor (77-86); on-line & INDEX MEDICUS search EROLINES (77-86); RN given refers to ((5'alpha)-isomer). ergocristine : Ergotaman bearing benzyl, hydroxy, and isopropyl groups at the 5', 12' and 2' positions, respectively, and oxo groups at positions 3', 6', and 18. It is a natural ergot alkaloid.	2.04	1	0	ergot alkaloid
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	4.66	9	0	benzenes; phenyl acetates
cetylpyridinium chloride anhydrous tserigel: according to first source contains polyvinylbutyral & cetylpyridinium chloride; UD only lists cetylpyridinium chloride as constituent. cetylpyridinium chloride : A pyridinium salt that has N-hexadecylpyridinium as the cation and chloride as the anion. It has antiseptic properties and is used in solutions or lozenges for the treatment of minor infections of the mouth and throat.	3.47	1	1	chloride salt; organic chloride salt	antiseptic drug; surfactant
triamcinolone Triamcinolone: A glucocorticoid given, as the free alcohol or in esterified form, orally, intramuscularly, by local injection, by inhalation, or applied topically in the management of various disorders in which corticosteroids are indicated. (From Martindale, The Extra Pharmacopoeia, 30th ed, p739). triamcinolone : A C21-steroid hormone that is 1,4-pregnadiene-3,20-dione carrying four hydroxy substituents at positions 11beta, 16alpha, 17alpha and 21 as well as a fluoro substituent at position 9. Used in the form of its 16,17-acetonide to treat various skin infections.	1.97	1	0	11beta-hydroxy steroid; 16alpha-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid hormone; fluorinated steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	anti-allergic agent; anti-inflammatory drug
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.	8.26	80	4	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
pyrene pyrene: structure in Merck Index, 9th ed, #7746. pyrene : An ortho- and peri-fused polycyclic arene consisting of four fused benzene rings, resulting in a flat aromatic system.	2.44	2	0	ortho- and peri-fused polycyclic arene	fluorescent probe; persistent organic pollutant
isothiuronium Isothiuronium: An undecenyl THIOUREA which may have topical anti-inflammatory activity.	2.44	2	0
4-methoxyamphetamine 4-methoxyamphetamine: para-methoxy derivative to amphetamine with hallucinogenic properties; minor descriptor (75-86); on line & INDEX MEDICUS search AMPHETAMINES (75-86); RN given refers to parent compound without isomeric designation	2.11	1	0
du-21220 Ritodrine: An adrenergic beta-2 agonist used to control PREMATURE LABOR.. 4-[2-[[1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]phenol : A secondary amino compound that is 4-(2-amino-1-hydroxypropyl)phenol in which one of the hydrogens attached to the nitrogen is replaced by a 2-(4-hydroxyphenyl)ethyl group.	2.04	1	0	benzyl alcohols; polyphenol; secondary alcohol; secondary amino compound
8-bromo cyclic adenosine monophosphate 8-Bromo Cyclic Adenosine Monophosphate: A long-acting derivative of cyclic AMP. It is an activator of cyclic AMP-dependent protein kinase, but resistant to degradation by cyclic AMP phosphodiesterase.. 8-Br-cAMP : A 3',5'-cyclic purine nucleotide that is 3',5'-cyclic AMP bearing an additional bromo substituent at position 8 on the adenine ring. An activator of cyclic AMP-dependent protein kinase, but resistant to degradation by cyclic AMP phosphodiesterase.	1.98	1	0	3',5'-cyclic purine nucleotide; adenyl ribonucleotide; organobromine compound	antidepressant; protein kinase agonist
transferrin Transferrin: An iron-binding beta1-globulin that is synthesized in the LIVER and secreted into the blood. It plays a central role in the transport of IRON throughout the circulation. A variety of transferrin isoforms exist in humans, including some that are considered markers for specific disease states.	2.42	2	0
rose bengal b disodium salt [no description available]	1.99	1	0
glutamic acid Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.	2.69	3	0	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
adenylyl imidodiphosphate Adenylyl Imidodiphosphate: 5'-Adenylic acid, monoanhydride with imidodiphosphoric acid. An analog of ATP, in which the oxygen atom bridging the beta to the gamma phosphate is replaced by a nitrogen atom. It is a potent competitive inhibitor of soluble and membrane-bound mitochondrial ATPase and also inhibits ATP-dependent reactions of oxidative phosphorylation.	1.98	1	0	adenosine 5'-phosphate
sodium azide Sodium Azide: A cytochrome oxidase inhibitor which is a nitridizing agent and an inhibitor of terminal oxidation. (From Merck Index, 12th ed). sodium azide : The sodium salt of hydrogen azide (hydrazoic acid).	1.98	1	0	inorganic sodium salt	antibacterial agent; explosive; mitochondrial respiratory-chain inhibitor; mutagen
azides Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.	3.48	8	0	pseudohalide anion	mitochondrial respiratory-chain inhibitor
adenosine diphosphate ribose Adenosine Diphosphate Ribose: An ester formed between the aldehydic carbon of RIBOSE and the terminal phosphate of ADENOSINE DIPHOSPHATE. It is produced by the hydrolysis of nicotinamide-adenine dinucleotide (NAD) by a variety of enzymes, some of which transfer an ADP-ribosyl group to target proteins.	2.05	1	0	ADP-sugar	Escherichia coli metabolite; mouse metabolite
amoxicillin Amoxicillin: A broad-spectrum semisynthetic antibiotic similar to AMPICILLIN except that its resistance to gastric acid permits higher serum levels with oral administration.. amoxicillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-(4-hydroxyphenyl)acetamido group.	2.43	2	0	penicillin allergen; penicillin	antibacterial drug
timolol (S)-timolol (anhydrous) : The (S)-(-) (more active) enantiomer of timolol. A beta-adrenergic antagonist, both the hemihydrate and the maleate salt are used in the mangement of glaucoma, hypertension, angina pectoris and myocardial infarction, and for the prevention of migraine.	2.46	2	0	timolol	anti-arrhythmia drug; antiglaucoma drug; antihypertensive agent; beta-adrenergic antagonist
nigericin Nigericin: A polyether antibiotic which affects ion transport and ATPase activity in mitochondria. It is produced by Streptomyces hygroscopicus. (From Merck Index, 11th ed). nigericin : A polyether antibiotic which affects ion transport and ATPase activity in mitochondria. It is produced by Streptomyces hygroscopicus.	2.06	1	0	polycyclic ether	antibacterial agent; antimicrobial agent; bacterial metabolite; potassium ionophore
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.	4.63	8	0	azide; pyrimidine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; HIV-1 reverse transcriptase inhibitor
b 10610 iodoxamic acid: radiopaque medium used in the diagnosis of gall bladder & bile duct diseases, usually as meglumine salt; minor descriptor (81-86); on-line & INDEX MEDICUS search TRIIODOBENZOIC ACIDS (81-86)	1.95	1	0	organic molecular entity
tobramycin Tobramycin: An aminoglycoside, broad-spectrum antibiotic produced by Streptomyces tenebrarius. It is effective against gram-negative bacteria, especially the PSEUDOMONAS species. It is a 10% component of the antibiotic complex, NEBRAMYCIN, produced by the same species.. tobramycin : A amino cyclitol glycoside that is kanamycin B lacking the 3-hydroxy substituent from the 2,6-diaminoglucose ring.	2.41	1	0	amino cyclitol glycoside	antibacterial agent; antimicrobial agent; toxin
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).	4.62	8	0	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
etoposide [no description available]	4.82	10	0	beta-D-glucoside; furonaphthodioxole; organic heterotetracyclic compound	antineoplastic agent; DNA synthesis inhibitor
substance p [no description available]	3.09	5	0	peptide	neurokinin-1 receptor agonist; neurotransmitter; vasodilator agent
promegestone Promegestone: A synthetic progestin which is useful for the study of progestin distribution and progestin tissue receptors, as it is not bound by transcortin and binds to progesterone receptors with a higher association constant than progesterone.. promegestone : A progestin consisting of 17beta-propionylestra-4,9-dien-3-one substituted at position 17 by a methyl group.	1.98	1	0	20-oxo steroid; 3-oxo-Delta(4) steroid	antineoplastic agent; progesterone receptor agonist; progestin
amikacin Amikacin: A broad-spectrum antibiotic derived from KANAMYCIN. It is reno- and oto-toxic like the other aminoglycoside antibiotics.. amikacin : An amino cyclitol glycoside that is kanamycin A acylated at the N-1 position by a 4-amino-2-hydroxybutyryl group.	2	1	0	alpha-D-glucoside; amino cyclitol glycoside; aminoglycoside; carboxamide	antibacterial drug; antimicrobial agent; nephrotoxin
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.	2.39	2	0	butyrate ester; phorbol ester; tertiary alpha-hydroxy ketone
methyldopa Methyldopa: An alpha-2 adrenergic agonist that has both central and peripheral nervous system effects. Its primary clinical use is as an antihypertensive agent.. alpha-methyl-L-dopa : A derivative of L-tyrosine having a methyl group at the alpha-position and an additional hydroxy group at the 3-position on the phenyl ring.	2.06	1	0	L-tyrosine derivative; non-proteinogenic L-alpha-amino acid	alpha-adrenergic agonist; antihypertensive agent; hapten; peripheral nervous system drug; sympatholytic agent
bezafibrate [no description available]	2.08	1	0	aromatic ether; monocarboxylic acid amide; monocarboxylic acid; monochlorobenzenes	antilipemic drug; environmental contaminant; geroprotector; xenobiotic
sq-11725 Nadolol: A non-selective beta-adrenergic antagonist with a long half-life, used in cardiovascular disease to treat arrhythmias, angina pectoris, and hypertension. Nadolol is also used for MIGRAINE DISORDERS and for tremor.. nadolol : Nadolol is a diastereoisomeric mixture consisting of equimolar amounts of the four possible 2,3-cis-isomers of 5-[3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydronaphthalene-2,3-diol.	2.47	2	0
1,8-dinitropyrene [no description available]	1.97	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.	2.94	4	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
1-methyl-4-phenylpyridinium 1-Methyl-4-phenylpyridinium: An active neurotoxic metabolite of 1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE. The compound reduces dopamine levels, inhibits the biosynthesis of catecholamines, depletes cardiac norepinephrine and inactivates tyrosine hydroxylase. These and other toxic effects lead to cessation of oxidative phosphorylation, ATP depletion, and cell death. The compound, which is related to PARAQUAT, has also been used as an herbicide.. N-methyl-4-phenylpyridinium : A pyridinium ion that is N-methylpyridinium having a phenyl substituent at the 4-position.	2.95	4	0	pyridinium ion	apoptosis inducer; herbicide; human xenobiotic metabolite; neurotoxin
vecuronium bromide Vecuronium Bromide: Monoquaternary homolog of PANCURONIUM. A non-depolarizing neuromuscular blocking agent with shorter duration of action than pancuronium. Its lack of significant cardiovascular effects and lack of dependence on good kidney function for elimination as well as its short duration of action and easy reversibility provide advantages over, or alternatives to, other established neuromuscular blocking agents.. vecuronium bromide : The organic bromide salt of a 5alpha-androstane compound having 3alpha-acetoxy-, 17beta-acetoxy-, 2beta-piperidinino- and 16beta-N-methylpiperidinium substituents.	2.88	4	0	organic bromide salt; quaternary ammonium salt	muscle relaxant; neuromuscular agent; nicotinic antagonist
vecuronium vecuronium : A 5alpha-androstane compound having 3alpha-acetoxy-, 17beta-acetoxy-, 2beta-piperidino- and 16beta-N-methylpiperidinium substituents.	1.99	1	0	acetate ester; androstane; quaternary ammonium ion	drug allergen; muscle relaxant; neuromuscular agent; nicotinic antagonist
ng-nitroarginine methyl ester NG-Nitroarginine Methyl Ester: A non-selective inhibitor of nitric oxide synthase. It has been used experimentally to induce hypertension.	4.08	15	0	alpha-amino acid ester; L-arginine derivative; methyl ester; N-nitro compound	EC 1.14.13.39 (nitric oxide synthase) 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.	1.98	1	0	diol; nitrosamine; secondary alcohol	carcinogenic agent
epirubicin Epirubicin: An anthracycline which is the 4'-epi-isomer of doxorubicin. The compound exerts its antitumor effects by interference with the synthesis and function of DNA.	1.97	1	0	aminoglycoside; anthracycline antibiotic; anthracycline; deoxy hexoside; monosaccharide derivative; p-quinones; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	antimicrobial agent; antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
cefmetazole Cefmetazole: A semisynthetic cephamycin antibiotic with a broad spectrum of activity against both gram-positive and gram-negative microorganisms. It has a high rate of efficacy in many types of infection and to date no severe side effects have been noted.. cefmetazole : A second-generation cephalosporin antibiotic having N(1)-methyltetrazol-5-ylthiomethyl, {[(cyanomethyl)sulfanyl]acetyl}amino and methoxy side-groups at positions 3, 7beta and 7alpha respectively of the parent cephem bicyclic structure.	2.37	2	0	cephalosporin	antibacterial drug
idarubicin Idarubicin: An orally administered anthracycline antineoplastic. The compound has shown activity against BREAST NEOPLASMS; LYMPHOMA; and LEUKEMIA.	1.99	1	0	anthracycline antibiotic; deoxy hexoside; monosaccharide derivative
piperacillin Piperacillin: Semisynthetic, broad-spectrum, AMPICILLIN derived ureidopenicillin antibiotic proposed for PSEUDOMONAS infections. It is also used in combination with other antibiotics.. piperacillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-[(4-ethyl-2,3-dioxopiperazin-1-yl)carboxamido]-2-phenylacetamido group.	2.4	2	0	penicillin allergen; penicillin	antibacterial drug
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.	2.07	1	0	aromatic ether; benzodioxoles; organofluorine compound; piperidines	antidepressant; anxiolytic drug; hepatotoxic agent; P450 inhibitor; serotonin uptake inhibitor
captopril Captopril: A potent and specific inhibitor of PEPTIDYL-DIPEPTIDASE A. It blocks the conversion of ANGIOTENSIN I to ANGIOTENSIN II, a vasoconstrictor and important regulator of arterial blood pressure. Captopril acts to suppress the RENIN-ANGIOTENSIN SYSTEM and inhibits pressure responses to exogenous angiotensin.. captopril : A L-proline derivative in which L-proline is substituted on nitrogen with a (2S)-2-methyl-3-sulfanylpropanoyl group. It is used as an anti-hypertensive ACE inhibitor drug.	4.24	5	0	alkanethiol; L-proline derivative; N-acylpyrrolidine; pyrrolidinemonocarboxylic acid	antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor
cefoperazone Cefoperazone: Semisynthetic broad-spectrum cephalosporin with a tetrazolyl moiety that is resistant to beta-lactamase. It may be used to treat Pseudomonas infections.. cefoperazone : A semi-synthetic parenteral cephalosporin with a tetrazolyl moiety that confers beta-lactamase resistance.	3.1	5	0	cephalosporin	antibacterial 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.	3.09	5	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
cefadroxil anhydrous Cefadroxil: Long-acting, broad-spectrum, water-soluble, CEPHALEXIN derivative.. cefadroxil : A cephalosporin bearing methyl and (2R)-2-amino-2-(4-hydroxyphenyl)acetamido groups at positions 3 and 7, respectively, of the cephem skeleton.	4.05	4	0	cephalosporin	antibacterial drug
buserelin Buserelin: A potent synthetic analog of GONADOTROPIN-RELEASING HORMONE with D-serine substitution at residue 6, glycine10 deletion, and other modifications.	2.02	1	0	oligopeptide
tiotidine tiotidine: UD gives slightly different structure for this cpd; RN given refers to parent cpd; structure in first source	2.06	1	0	thiazoles
cefaclor anhydrous Cefaclor: Semisynthetic, broad-spectrum antibiotic derivative of CEPHALEXIN.. cefaclor : A cephalosporin bearing chloro and (R)-2-amino-2-phenylacetamido groups at positions 3 and 7, respectively, of the cephem skeleton.	3.15	1	0	cephalosporin	antibacterial drug; drug allergen
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.	2.06	1	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).	3.5	8	0	delta-lactone; fatty acid ester; hexahydronaphthalenes; polyketide; statin (naturally occurring)	anticholesteremic drug; antineoplastic agent; Aspergillus metabolite; prodrug
3-chloro-4-(dichloromethyl)-5-hydroxy-2(5h)-furanone 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone: structure given in first source	1.98	1	0	butenolide
castanospermine castanospermine: indolizidine alkaloid from seeds of Australian legume, Castanospermum australe. castanospermine : A tetrahydroxyindolizidine alkaloid that consists of octahydroindolizine having four hydroxy substituents located at positions 1, 6, 7 and 8 (the 1S,6S,7R,8R,8aR-diastereomer).	2.13	1	0	indolizidine alkaloid	anti-HIV-1 agent; anti-inflammatory agent; EC 3.2.1.* (glycosidase) inhibitor; metabolite
simvastatin Simvastatin: A derivative of LOVASTATIN and potent competitive inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A reductase (HYDROXYMETHYLGLUTARYL COA REDUCTASES), which is the rate-limiting enzyme in cholesterol biosynthesis. It may also interfere with steroid hormone production. Due to the induction of hepatic LDL RECEPTORS, it increases breakdown of LDL CHOLESTEROL.. simvastatin : A member of the class of hexahydronaphthalenes that is lovastatin in which the 2-methylbutyrate ester moiety has been replaced by a 2,2-dimethylbutyrate ester group. It is used as a cholesterol-lowering and anti-cardiovascular disease drug.	3.65	9	0	delta-lactone; fatty acid ester; hexahydronaphthalenes; statin (semi-synthetic)	EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor; EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor; ferroptosis inducer; geroprotector; prodrug
pravastatin Pravastatin: An antilipemic fungal metabolite isolated from cultures of Nocardia autotrophica. It acts as a competitive inhibitor of HMG CoA reductase (HYDROXYMETHYLGLUTARYL COA REDUCTASES).. pravastatin : A carboxylic ester resulting from the formal condensation of (S)-2-methylbutyric acid with the hydroxy group adjacent to the ring junction of (3R,5R)-7-[(1S,2S,6S,8S,8aR)-6,8-dihydroxy-2-methyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid. Derived from microbial transformation of mevastatin, pravastatin is a reversible inhibitor of 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA). The sodium salt is used for lowering cholesterol and preventing cardiovascular disease. It is one of the lower potency statins, but has the advantage of fewer side effects compared with lovastatin and simvastatin.	5.73	26	0	3-hydroxy carboxylic acid; carbobicyclic compound; carboxylic ester; hydroxy monocarboxylic acid; secondary alcohol; statin (semi-synthetic)	anticholesteremic drug; environmental contaminant; metabolite; xenobiotic
atomoxetine atomoxetine : A secondary amino compound having methyl and 3-(2-methylphenoxy)-3-phenylpropan-1-yl substituents.	2.46	2	0	aromatic ether; secondary amino compound; toluenes	adrenergic uptake inhibitor; antidepressant; environmental contaminant; xenobiotic
raloxifene hydrochloride Raloxifene Hydrochloride: A second generation selective estrogen receptor modulator (SERM) used to prevent osteoporosis in postmenopausal women. It has estrogen agonist effects on bone and cholesterol metabolism but behaves as a complete estrogen antagonist on mammary gland and uterine tissue.. raloxifene hydrochloride : A hydrochloride salt resulting from the reaction of equimolar amounts of raloxifene and hydrogen chloride.	2.13	1	0	hydrochloride	bone density conservation agent; estrogen antagonist; estrogen receptor modulator
mifepristone Mifepristone: A progestational and glucocorticoid hormone antagonist. Its inhibition of progesterone induces bleeding during the luteal phase and in early pregnancy by releasing endogenous prostaglandins from the endometrium or decidua. As a glucocorticoid receptor antagonist, the drug has been used to treat hypercortisolism in patients with nonpituitary CUSHING SYNDROME.	2.95	4	0	3-oxo-Delta(4) steroid; acetylenic compound; tertiary amino compound	abortifacient; contraceptive drug; hormone antagonist; synthetic oral contraceptive
5-propynylarabinofuranosyluracil 5-propynylarabinofuranosyluracil: potent inhibitor of VZV	2.06	1	0
itraconazole Itraconazole: A triazole antifungal agent that inhibits cytochrome P-450-dependent enzymes required for ERGOSTEROL synthesis.. itraconazole : An N-arylpiperazine that is cis-ketoconazole in which the imidazol-1-yl group is replaced by a 1,2,4-triazol-1-yl group and in which the actyl group attached to the piperazine moiety is replaced by a p-[(+-)1-sec-butyl-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl]phenyl group. A potent P-glycoprotein and CYP3A4 inhibitor, it is used as an antifungal drug for the treatment of various fungal infections, including aspergillosis, blastomycosis, candidiasis, chromoblastomycosis, coccidioidomycosis, cryptococcosis, histoplasmosis, and sporotrichosis.	2.11	1	0	aromatic ether; conazole antifungal drug; cyclic ketal; dichlorobenzene; dioxolane; N-arylpiperazine; triazole antifungal drug; triazoles	EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor; Hedgehog signaling pathway inhibitor; P450 inhibitor
ranolazine Ranolazine: An acetanilide and piperazine derivative that functions as a SODIUM CHANNEL BLOCKER and prevents the release of enzymes during MYOCARDIAL ISCHEMIA. It is used in the treatment of ANGINA PECTORIS.. N-(2,6-dimethylphenyl)-2-{4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl}acetamide : An aromatic amide obtained by formal condensation of the carboxy group of 2-{4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl}acetic acid with the amino group of 2,6-dimethylaniline.. ranolazine : A racemate comprising equal amounts of (R)- and (S)-ranolazine. Used for treatment of chronic angina.	2.07	1	0	aromatic amide; monocarboxylic acid amide; monomethoxybenzene; N-alkylpiperazine; secondary alcohol
adefovir adefovir: inhibitor of African swine fever virus. adefovir(1-) : A organophosphonate oxoanion obtained by removal of a proton from the phosphonate group of adefovir, a nucleoside reverse transcriptase inhibitor. It is the major microspecies at pH 7.3 (according to Marvin v 6.2.0.).. adefovir : A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens has been replaced by a 2-(6-amino-9H-purin-9-yl)ethoxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(t-butoxycarbonyloxymethyl) ester (dipivoxil ester) prodrug is used to treat chronic hepatitis B viral infection.	3.55	2	0	6-aminopurines; ether; phosphonic acids	antiviral drug; DNA synthesis inhibitor; drug metabolite; HIV-1 reverse transcriptase inhibitor; nephrotoxic agent
loxiglumide loxiglumide: cholecystokinin receptor antagonist; RN refers to (+-)-isomer; structure in first source	3.24	6	0	organic molecular entity
sparfloxacin [no description available]	2.04	1	0	fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone
cidofovir anhydrous Cidofovir: An acyclic nucleoside phosphonate that acts as a competitive inhibitor of viral DNA polymerases. It is used in the treatment of RETINITIS caused by CYTOMEGALOVIRUS INFECTIONS and may also be useful for treating HERPESVIRUS INFECTIONS.. cidofovir anhydrous : Cytosine substituted at the 1 position by a 3-hydroxy-2-(phosphonomethoxy)propyl group (S configuration). A nucleoside analogue, it is an injectable antiviral used for the treatment of cytomegalovirus (CMV) retinitis in AIDS patients.	3.15	1	0	phosphonic acids; pyrimidone	anti-HIV agent; antineoplastic agent; antiviral drug; photosensitizing agent
mibefradil Mibefradil: A benzimidazoyl-substituted tetraline that selectively binds and inhibits CALCIUM CHANNELS, T-TYPE.	2.06	1	0	tetralins	T-type calcium channel blocker
topotecan Topotecan: An antineoplastic agent used to treat ovarian cancer. It works by inhibiting DNA TOPOISOMERASES, TYPE I.. topotecan : A pyranoindolizinoquinoline used as an antineoplastic agent. It is a derivative of camptothecin and works by binding to the topoisomerase I-DNA complex and preventing religation of these 328 single strand breaks.	3.57	2	0	pyranoindolizinoquinoline	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor
tenidap tenidap: structure given in first source; RN refers to (Z)-isomer	2.06	1	0
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.	2.11	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
atorvastatin [no description available]	3.16	5	0	aromatic amide; dihydroxy monocarboxylic acid; monofluorobenzenes; pyrroles; statin (synthetic)	environmental contaminant; xenobiotic
befloxatone befloxatone: selectively inhibits monoamine oxidase A; structure in first source; RN given refers to (R)-isomer	2.06	1	0
lamivudine [no description available]	3.15	1	0	monothioacetal; nucleoside analogue; oxacycle; primary alcohol	allergen; anti-HBV agent; antiviral drug; EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor; HIV-1 reverse transcriptase inhibitor; prodrug
irinotecan [no description available]	4.24	5	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
pobilukast pobilukast: a leukotriene receptor antagonist; an antiasthmatic agent; structure in first source; RN refers to (R-(R,S)-isomer	1.97	1	0
valsartan Valsartan: A tetrazole derivative and ANGIOTENSIN II TYPE 1 RECEPTOR BLOCKER that is used to treat HYPERTENSION.. valsartan : A monocarboxylic acid amide consisting of L-valine in which the amino hydrogens have been replaced by a pentanoyl and a [2'-(1H-tetrazol-5-yl)biphenyl]-4-yl]methyl group. It exhibits antihypertensive activity.	3.57	2	0	biphenylyltetrazole; monocarboxylic acid amide; monocarboxylic acid	angiotensin receptor antagonist; antihypertensive agent; environmental contaminant; xenobiotic
ziprasidone ziprasidone: a benzisothiazoylpiperazine derivative; has combined dopamine and serotonin receptor antagonist activity; structurally related to tiospirone. ziprasidone : A piperazine compound having 1,2-benzothiazol-3-yl- and 2-(6-chloro-1,3-dihydro-2-oxindol-5-yl)ethyl substituents attached to the nitrogen atoms.	2.06	1	0	1,2-benzisothiazole; indolones; organochlorine compound; piperazines	antipsychotic agent; dopaminergic antagonist; histamine antagonist; muscarinic antagonist; psychotropic drug; serotonergic antagonist
adefovir dipivoxil bis(pivaloyloxymethyl)-9-(2-phosphonylmethoxyethyl)adenine: structure given in first source. adefovir pivoxil : An organic phosphonate that is the dipivoxil ester of adefovir. A prodrug for adefovir, an HIV-1 reverse transcriptase inhibitor, adefovir pivoxil is used to treat chronic hepatitis B viral infection.	2.21	1	0	6-aminopurines; carbonate ester; ether; organic phosphonate	antiviral drug; DNA synthesis inhibitor; HIV-1 reverse transcriptase inhibitor; nephrotoxic agent; prodrug
emtricitabine Emtricitabine: A deoxycytidine analog and REVERSE TRANSCRIPTASE INHIBITOR with antiviral activity against HIV-1 and HEPATITIS B viruses. It is used to treat HIV INFECTIONS.. emtricitabine : An organofluorine compound that is 5-fluorocytosine substituted at the 1 position by a 2-(hydroxymethyl)-1,3-oxathiolan-5-yl group (2R,5S configuration). It is used in combination therapy for the treatment of HIV-1 infection.	3.57	2	0	monothioacetal; nucleoside analogue; organofluorine compound; pyrimidone	antiviral drug; HIV-1 reverse transcriptase inhibitor
adenosine quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit	3.5	8	0	adenosines; purines D-ribonucleoside	analgesic; anti-arrhythmia drug; fundamental metabolite; human metabolite; vasodilator agent
gadolinium chloride gadolinium chloride: a macrophage inhibitor; reduces pulmonary injury and inflammatory mediator production induced by inhaled ozone	2.05	1	0	gadolinium coordination entity	TRP channel blocker
d-lactic acid (R)-lactic acid : An optically active form of lactic acid having (R)-configuration.	2.02	1	0	2-hydroxypropanoic acid	Escherichia coli metabolite; human metabolite
vanadates Vanadates: Oxyvanadium ions in various states of oxidation. They act primarily as ion transport inhibitors due to their inhibition of Na(+)-, K(+)-, and Ca(+)-ATPase transport systems. They also have insulin-like action, positive inotropic action on cardiac ventricular muscle, and other metabolic effects.. vanadate(3-) : A vanadium oxoanion that is a trianion with formula VO4 in which the vanadium is in the +5 oxidation state and is attached to four oxygen atoms.	2.89	4	0	trivalent inorganic anion; vanadium oxoanion	EC 3.1.3.1 (alkaline phosphatase) inhibitor; EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; EC 3.1.3.41 (4-nitrophenylphosphatase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor
dimethylhydrazines Dimethylhydrazines: Hydrazines substituted with two methyl groups in any position.	1.95	1	0
acridine orange Acridine Orange: A cationic cytochemical stain specific for cell nuclei, especially DNA. It is used as a supravital stain and in fluorescence cytochemistry. It may cause mutations in microorganisms.. acridine orange : Fluorescent dye useful for cell cycle determination. It is cell-permeable, and interacts with DNA and RNA by intercalation or electrostatic attractions respectively.. acridine orange free base : A member of the class of aminoacridines that is acridine carrying two dimethylamino substituents at positions 3 and 6. The hydrochloride salt is the fluorescent dye 'acridine orange', used for cell cycle determination.	2.68	3	0	aminoacridines; aromatic amine; tertiary amino compound	fluorochrome; histological dye
colestipol Colestipol: Highly crosslinked and insoluble basic anion exchange resin used as anticholesteremic. It may also may reduce triglyceride levels.. colestipol : A high molecular weight copolymer of diethylenetriamine and epichlorohydrin (hydrochloride), with approximately 1 out of 5 amine nitrogens protonated. Due to the highly cross-linked and insoluble nature of the material, no structural formula has been assigned and no specific molecular weight information is available. A basic anion exchange resin, it is used as its hydrochloride for binding bile acids in the intestine, inhibiting their reabsorption.	3.68	2	0
octyl glucoside octyl-beta-D-glucoside: RN given refers to (beta)-isomer. octyl beta-D-glucopyranoside : An beta-D-glucoside in which the anomeric hydrogen of beta-D-glucopyranose is substituted by an octyl group.	1.98	1	0	beta-D-glucoside	plant metabolite
trazodone hydrochloride Triticum: A plant genus of the family POACEAE that is the source of EDIBLE GRAIN. A hybrid with rye (SECALE CEREALE) is called TRITICALE. The seed is ground into FLOUR and used to make BREAD, and is the source of WHEAT GERM AGGLUTININS.. trazodone hydrochloride : A hydrochloride salt prepared from equimolar amounts of trazodone and hydrogen chloride.	3.06	5	0	hydrochloride	adrenergic antagonist; antidepressant; H1-receptor antagonist; sedative; serotonin uptake inhibitor
trovafloxacin trovafloxacin: a trifluoronaphthyridone derivative of 7-(3-azabicyclo(3.1.0)hexyl)naphthyridone; has antineoplastic activity. trovafloxacin : A 1,8-naphthyridine derivative that is 4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid bearing additional 2,4-difluorophenyl, fluoro and 6-amino-3-azabicyclo[3.1.0]hex-3-yl substituents at positions 1, 6 and 7 respectively. A broad-spectrum antibiotic that was withdrawn from the market due to risk of liver failure.	2.06	1	0
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.	3.84	3	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.	2.07	1	0	aryl sulfide; benzamides; organic heterobicyclic compound; phenols; secondary alcohol; tertiary amino compound	antineoplastic agent; HIV protease inhibitor
glucose, (beta-d)-isomer beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.	4.58	8	0	D-glucopyranose	epitope; mouse metabolite
n-methylnicotinamide N-methylnicotinamide: structure. N-methylnicotinamide : A pyridinecarboxamide that is nicotinamide in which one of the amide hydrogens is substituted by a methyl group.	2.93	4	0	pyridinecarboxamide	metabolite
thiazolyl blue thiazolyl blue: RN & II refers to bromide. 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide : The bromide salt of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium.	2.44	2	0	organic bromide salt	colorimetric reagent; dye
baicalin [no description available]	3.45	7	0	dihydroxyflavone; glucosiduronic acid; glycosyloxyflavone; monosaccharide derivative	antiatherosclerotic agent; antibacterial agent; anticoronaviral agent; antineoplastic agent; antioxidant; cardioprotective agent; EC 2.7.7.48 (RNA-directed RNA polymerase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; ferroptosis inhibitor; neuroprotective agent; non-steroidal anti-inflammatory drug; plant metabolite; prodrug
plerixafor plerixafor: a bicyclam derivate, highly potent & selective inhibitor of HIV-1 & HIV-2. plerixafor : An azamacrocycle consisting of two cyclam rings connected by a 1,4-phenylenebis(methylene) linker. It is a CXCR4 chemokine receptor antagonist and a hematopoietic stem cell mobilizer. It is used in combination with grulocyte-colony stimulating factor (G-CSF) to mobilize hematopoietic stem cells to the perpheral blood for collection and subsequent autologous transplantation in patients with non-Hodgkin's lymphoma and multiple myeloma.	2	1	0	azacycloalkane; azamacrocycle; benzenes; crown amine; secondary amino compound; tertiary amino compound	anti-HIV agent; antineoplastic agent; C-X-C chemokine receptor type 4 antagonist; immunological adjuvant
amprenavir [no description available]	2.07	1	0	carbamate ester; sulfonamide; tetrahydrofuryl ester	antiviral drug; HIV protease inhibitor
epigallocatechin gallate epigallocatechin gallate: a steroid 5alpha-reductase inhibitor and antimutagen in green tea (Camellia sinensis). (-)-epigallocatechin 3-gallate : A gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (-)-epigallocatechin.	3.63	2	0	flavans; gallate ester; polyphenol	antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite
fluorexon fluorexon: structure	2.94	4	0	xanthene dye	fluorochrome
25-hydroxycholesterol [no description available]	2.02	1	0	25-hydroxy steroid; oxysterol	human metabolite
10,10'-dimethyl-9,9'-biacridinium 10,10'-dimethyl-9,9'-biacridinium: chemoluminescent probe; RN given refers to dinitrate; Lucigenin refers to dinitrate	1.97	1	0
1,2-distearoyllecithin [no description available]	1.98	1	0
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.	2.94	4	0	dithiocarbamic acids; pyrrolidines	anticonvulsant; antineoplastic agent; geroprotector; neuroprotective agent; NF-kappaB inhibitor; radical scavenger
glutathione disulfide Glutathione Disulfide: A GLUTATHIONE dimer formed by a disulfide bond between the cysteine sulfhydryl side chains during the course of being oxidized.	3.24	6	0	glutathione derivative; organic disulfide	Escherichia coli metabolite; mouse metabolite
5-bromo-4-chloro-3-indoxyl phosphate 5-bromo-4-chloro-3-indoxyl phosphate: substrate for demonstration of activity of alkaline phosphatase; structure given in first source. 5-bromo-4-chloro-3-indolyl phosphate : An aryl phosphate that is indoxyl phopshate in which the indole moiety is substituted at positions 4 and 5 by chlorine and bromine, respectively. It is used to test for the presence of an enzyme, alkaline phosphatase, which cleaves the phosphate group to give 5-bromo-4-chloroindoxyl, which immediately dimerises to give an intensely blue product.	2	1	0	aryl phosphate; indoles; organobromine compound; organochlorine compound	chromogenic compound
cephalosporin c cephalosporin C: RN given refers to parent cpd; structure in Merck, 9th ed, #1937. cephalosporin C : A cephalosporin antibiotic carrying a 3-acetoxymethyl substituent and a 6-oxo-N(6)-L-lysino group at position 7.	3.1	5	0	cephalosporin	fungal metabolite
lathosterol lathosterol: RN given refers to (3beta,5alpha)-isomer. 5alpha-cholest-7-en-3beta-ol : A cholestanoid that is (5alpha)-cholest-7-ene substituted by a beta-hydroxy group at position 3.	4.1	3	1	3beta-sterol; C27-steroid; cholestanoid; Delta(7)-sterol	human metabolite; mouse metabolite
azuletil azuletil: RN given refers to parent cpd. egualen : A member of the class of azulenes carrying sulfo, ethyl and isopropyl substituents at positions 1, 3 and 7 respectively. Used (in the form of its sodium salt) for treatment of gastric ulcers.	1.99	1	0	arenesulfonic acid; azulenes	anti-ulcer drug; thromboxane A2 antagonist
leminoprazole [no description available]	1.99	1	0
web 2086 WEB 2086: structure given in first source; PAF antagonist	2.05	1	0	organonitrogen heterocyclic compound; organosulfur heterocyclic compound
4-(2-succinimidoethylthio)phenyl 4-guanidinobenzoate 4-(2-succinimidoethylthio)phenyl 4-guanidinobenzoate: potently inhibits trypsin, plasmin and thrombin	2.38	2	0
bepafant bepafant: RN given from Toxlit 6/90; PAF antagonist	2.03	1	0
azelnidipine azelnidipine: structure given in first source	2.02	1	0	isopropyl ester
repaglinide [no description available]	3.57	2	0	piperidines
iobitridol [no description available]	2.03	1	0	benzenedicarboxamide; hexol; organoiodine compound	environmental contaminant; radioopaque medium; xenobiotic
telmisartan Telmisartan: A biphenyl compound and benzimidazole derivative that acts as an angiotensin II type 1 receptor antagonist. It is used in the management of HYPERTENSION.. telmisartan : A member of the class of benzimidazoles used widely in the treatment of hypertension.	4.29	5	0	benzimidazoles; biphenyls; carboxybiphenyl	angiotensin receptor antagonist; antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; environmental contaminant; xenobiotic
estriol 3-sulfate estriol 3-sulfate: estriol conjugate; RN given refers to (16alpha,17beta)-isomer	2.01	1	0
estradiol-3-sulfate estradiol-3-sulfate: RN given refers to (17beta)-isomer. 17beta-estradiol 3-sulfate : A steroid sulfate obtained by the formal condensation of sulfuric acid with the 3-hydroxy group of 17beta-estradiol.	2.69	3	0	17beta-hydroxy steroid; steroid sulfate	mammalian metabolite
estradiol 3,17-disulfate estradiol 3,17-disulfate: RN given refers to (17beta)-isomer	2.01	1	0	steroid sulfate
benzeneboronic acid [no description available]	1.97	1	0	boronic acids
ethinyl estradiol-17-sulfate ethinyl estradiol-17-sulfate: RN given refers to the (17alpha)-isomer	1.99	1	0
triazoles Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.	2.73	3	0	1,2,3-triazole
2,4,6-trihydroxyacetophenone monoacetylphloroglucinol: structure in first source. 2',4',6'-trihydroxyacetophenone : A benzenetriol that is acetophenone in which the hydrogens at positions 2, 4, and 6 on the phenyl group are replaced by hydroxy groups. It is used as a matrix in matrix-assisted laser desorption/ionization (MALDI) mass spectrometry for the analysis of acidic glycans and glycopeptides.	2.03	1	0	aromatic ketone; benzenetriol; methyl ketone	MALDI matrix material; plant metabolite
harmol harmol: harmol is oxidized form of alkaloid harmolol; RN given refers to parent cpd; structure	1.97	1	0	harmala alkaloid
sanguinarine chloride [no description available]	2.04	1	0
ibuproxam ibuproxam: RN given refers to cpd without isomeric designation; structure in Negwer, 5th ed, #6312. ibuproxam : A hydroxamic acid obtained by formal condensation of the carboxy group of ibuprofen with the amino group of hydroxylamine. Used for treatment of pain and inflammation associated with musculoskeletal and joint disorders.	2.06	1	0	hydroxamic acid	iron chelator; non-narcotic analgesic; non-steroidal anti-inflammatory drug
glycyl-glycyl-glycyl-glycine [no description available]	2.01	1	0
2,6-dihydroxyacetophenone 2,6-dihydroxyacetophenone: inhibits aminopyrine-N-demethylase in rat liver microsomal preparations	2.03	1	0	aromatic ketone
triethylmethylammonium triethylmethylammonium: RN given refers to parent cpd	2.38	2	0
n-methylscopolamine N-Methylscopolamine: A muscarinic antagonist used to study binding characteristics of muscarinic cholinergic receptors.	2.06	1	0
uk 68798 [no description available]	2.07	1	0	aromatic ether; sulfonamide; tertiary amino compound	anti-arrhythmia drug; potassium channel blocker
ljc 10627 biapenem: structure given in first source. biapenem : A carbapenem antibiotic in which the azetidine and pyrroline rings carry 1-hydroxymethyl and pyrazolo[1,2-a][1,2,4]triazolium-6-ylthio substituents respectively.	2.04	1	0	carbapenems; organic sulfide; pyrazolotriazole	antibacterial drug
lecimibide [no description available]	1.98	1	0
tyloxapol tyloxapol: non-ionic detergent with surface-active properties; incompatible with metals; surfactant also used in inhalation therapy; N1 is from CA Vol 90 Form Index; N1 in Chemline is same as synonym 8. tyloxapol : A polymeric compound resulting from the reaction of 4-(1,1,3,3-tetramethylbutyl)phenol with formaldehyde to give a chain in which 6-8 molecules are linked together by CH2 groups ortho to the phenolic hydroxy groups, which have then undergone reaction with oxirane to give polyoxyethyleneoxy moieties, Ar(OCH2CH2)xOH, where x = 8-10. A nonionic liquic polymer, it inhibits lipoprotein lipase and hence clearance of triglyceride from the plasma, so is used to induce hyperlipidaemia in test animals. Also used as a surfactant to aid liquefaction and removal of mucus- and pus-containing bronchopulmonary secretions.	2.37	2	0
masoprocol Masoprocol: A potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. The compound also inhibits formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase to a lesser extent. It also serves as an antioxidant in fats and oils.. masoprocol : The meso-form of nordihydroguaiaretic acid. An antioxidant found in the creosote bush, Larrea divaricata, it is a potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. It also inhibits (though to a lesser extent) formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase.	2.38	2	0	nordihydroguaiaretic acid	antineoplastic agent; hypoglycemic agent; lipoxygenase inhibitor; metabolite
tocophersolan tocophersolan: RN given refers to parent cpd	2.21	1	0	tocol
bufuralol bufuralol: RN given refers to cpd without isomeric designation; structure	2.07	1	0	benzofurans
aceclofenac [no description available]	2.06	1	0	amino acid; carboxylic ester; dichlorobenzene; monocarboxylic acid; secondary amino compound	EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
fluparoxan fluparoxan: structure given in first source	2.06	1	0
cyclobutyrol cyclobutyrol: RN given refers to parent cpd; structure. cyclobutyrol : A hydroxy monocarboxylic acid in which the hydroxy group is geminal to a 1-carboxypropyl group on a cyclohexane ring.	1.97	1	0	hydroxy monocarboxylic acid	bile therapy drug
ubenimex ubenimex: growth inhibitor	3.82	3	0
sulfolithocholylglycine sulfoglycolithocholic acid : The 3-O-sulfo derivative of glycolithocholic acid.	2.91	4	0	bile acid glycine conjugate; steroid sulfate
sesamin (+)-sesamin : A lignan that consists of tetrahydro-1H,3H-furo[3,4-c]furan substituted by 1,3-benzodioxole groups at positions 1 and 4 (the 1S,3aR,4S,6aR stereoisomer). Isolated from Cinnamomum camphora, it exhibits cytotoxic activity.	1.97	1	0	benzodioxoles; furofuran; lignan	antineoplastic agent; neuroprotective agent; plant metabolite
chelerythrine chloride [no description available]	2.04	1	0
betulin betulin: isolated from various white birch bark (BETULA). betulin : A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-hydroxymethyl substituents.	3.51	1	0	diol; pentacyclic triterpenoid	analgesic; anti-inflammatory agent; antineoplastic agent; antiviral agent; metabolite
leupeptin [no description available]	1.98	1	0	aldehyde; tripeptide	bacterial metabolite; calpain inhibitor; cathepsin B inhibitor; EC 3.4.21.4 (trypsin) inhibitor; serine protease inhibitor
grepafloxacin grepafloxacin: structure in first source	2	1	0	fluoroquinolone antibiotic; quinolines; quinolone antibiotic
oleandomycin [no description available]	2.45	2	0	oleandomycins
doripenem Doripenem: A carbapenem derivative antibacterial agent that is more stable to renal dehydropeptidase I than IMIPENEM, but does not need to be given with an enzyme inhibitor such as CILASTATIN. It is used in the treatment of infections such as HOSPITAL-ACQUIRED PNEUMONIA, and complicated intra-abdominal or urinary-tract infections, including PYELONEPHRITIS.	2.41	1	0	carbapenems
bromosuccinic acid bromosuccinic acid: RN given refers to undesignated isomer. bromosuccinic acid : A dicarboxylic acid that is succinic acid substituted at position 2 by a bromine atom.	1.97	1	0	2-bromocarboxylic acid; dicarboxylic acid
4-nitrophenyl palmitate p-nitrophenyl palmitate : A palmitate ester obtained by condensation of the carboxy group of palmitic acid with the phenolic hydroxy group of p-nitrophenol.	1.97	1	0	C-nitro compound; hexadecanoate ester
tetrahexylammonium tetrahexylammonium: RN given refers to parent cpd	1.97	1	0
2-(methylamino)isobutyric acid alpha-(methylamino)isobutyric acid : A non-proteinogenic alpha-amino acid that is isobutyric acid in which the alpha-hydrogen has been replaced by a methylamino group.	2.37	2	0	alanine derivative; alpha-amino acid zwitterion; non-proteinogenic alpha-amino acid; secondary amino compound	human urinary metabolite
diethylphosphorocyanidate diethylphosphorocyanidate: reagent for solid phase peptide synthesis; structure	1.99	1	0
tri-n-butylmethylammonium tri-n-butylmethylammonium: RN given refers to iodide	2.67	3	0
6-carboxyfluorescein 6-carboxyfluorescein: originally sold as 6-carboxyfluorescein, but commercial product is a mixture of two isomers; correct name is 5(6)-carboxyfluorescein	2.9	4	0	monocarboxylic acid
rivastigmine [no description available]	2.46	2	0	carbamate ester; tertiary amino compound	cholinergic drug; EC 3.1.1.8 (cholinesterase) inhibitor; neuroprotective agent
eletriptan eletriptan: 5-HT(1B/1D) receptor agonist; structure in first source. eletriptan : An N-alkylpyrrolidine, that is N-methylpyrrolidine in which the pro-R hydrogen at position 2 is replaced by a {5-[2-(phenylsulfonyl)ethyl]-1H-indol-3-yl}methyl group.	2.07	1	0	indoles; N-alkylpyrrolidine; sulfone	non-steroidal anti-inflammatory drug; serotonergic agonist; vasoconstrictor agent
rosiglitazone [no description available]	4.1	4	0	aminopyridine; thiazolidinediones	EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor; ferroptosis inhibitor; insulin-sensitizing drug
1-nitro-2-phenylethane 1-nitro-2-phenylethane: component of Aniba canelilla essential oil with antinociceptive activity; structure in first source	2.1	1	0
gamma-glutamine-4-nitroanilide gamma-glutamine-4-nitroanilide: substrate for glutaminase B.; RN given refers to (L)-isomer	1.96	1	0
4-nitrophenylglucuronide 4-nitrophenyl beta-D-glucuronide : A beta-D-glucosiduronic acid having a 4-nitrophenyl substituent at the anomeric position.	2.04	1	0	beta-D-glucosiduronic acid; C-nitro compound	chromogenic compound
acetaminophen glucuronide acetaminophen glucuronide: acetaminophen metabolite in rats. acetaminophen O-beta-D-glucosiduronic acid : A beta-D-glucosiduronic acid that is the O-glucuronide of paracetamol (acetaminophen).	2.04	1	0	beta-D-glucosiduronic acid	drug metabolite
clarithromycin Clarithromycin: A semisynthetic macrolide antibiotic derived from ERYTHROMYCIN that is active against a variety of microorganisms. It can inhibit PROTEIN SYNTHESIS in BACTERIA by reversibly binding to the 50S ribosomal subunits. This inhibits the translocation of aminoacyl transfer-RNA and prevents peptide chain elongation.. clarithromycin : The 6-O-methyl ether of erythromycin A, clarithromycin is a macrolide antibiotic used in the treatment of respiratory-tract, skin and soft-tissue infections. It is also used to eradicate Helicobacter pylori in the treatment of peptic ulcer disease. It prevents bacteria from growing by interfering with their protein synthesis.	2.74	3	0	macrolide antibiotic	antibacterial drug; environmental contaminant; protein synthesis inhibitor; xenobiotic
cerium trihydroxide cerium hydroxide: phosphate binder; RN given refers to Ce(OH)	2	1	0
cholest-5-ene-3,4-diol cholest-5-ene-3,4-diol: RN given refers to (3beta,4beta)-isomer	2.25	1	0
dibromosulphthalein dibromosulphthalein: RN refers to 3H-labeled parent compound	3.49	8	0
coenzyme a [no description available]	3.05	5	0	adenosine 3',5'-bisphosphate	coenzyme; Escherichia coli metabolite; mouse metabolite
gentiopicroside gentiopicroside: a secoiridoid in Gentiana with rearrangement to two pyran rings	2.11	1	0	glycoside
mebeverine gamma-oryzanol: present in rice bran is associated with various physiological functions; RN given refers to gamma-oryzanol	2.05	1	0
nicotine (S)-nicotine : A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has S-configuration. The naturally occurring and most active enantiomer of nicotine, isolated from Nicotiana tabacum.	3.17	5	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
fibrinogen Fibrinogen: Plasma glycoprotein clotted by thrombin, composed of a dimer of three non-identical pairs of polypeptide chains (alpha, beta, gamma) held together by disulfide bonds. Fibrinogen clotting is a sol-gel change involving complex molecular arrangements: whereas fibrinogen is cleaved by thrombin to form polypeptides A and B, the proteolytic action of other enzymes yields different fibrinogen degradation products.. D-iditol : The D-enantiomer of iditol.	2.76	3	0	iditol	fungal metabolite
7-ketocholesterol 7-ketocholesterol: inhibits uptake of cholesterol in rabbit aorta. 7-ketocholesterol : A cholestanoid that consists of cholesterol bearing an oxo substituent at position 7.	2	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; 7-oxo steroid; cholestanoid	neuroprotective agent
homocysteine Homocysteine: A thiol-containing amino acid formed by a demethylation of METHIONINE.. homocysteine : A sulfur-containing amino acid consisting of a glycine core with a 2-mercaptoethyl side-chain.. L-homocysteine : A homocysteine that has L configuration.	2.05	1	0	amino acid zwitterion; homocysteine; serine family amino acid	fundamental metabolite; mouse metabolite
alpha,beta-methyleneadenosine 5'-triphosphate alpha,beta-methyleneadenosine 5'-triphosphate: do not confuse with beta,gamma-methylene ATP; RN given refers to parent cpd	1.98	1	0	nucleoside triphosphate analogue
8-((4-chlorophenyl)thio)cyclic-3',5'-amp 8-((4-chlorophenyl)thio)cyclic-3',5'-AMP: lowers cAMP in heart & fat cells; cAMP-dependent kinase inhibitor. 8-(4-chlorophenylthio)-cAMP : A 3',5'-cyclic purine nucleotide that is 3',5'-cyclic AMP in which the hydrogen at position 2 on the purine fragment is replaced by a 4-chlorophenylthio group.	2.39	2	0	3',5'-cyclic purine nucleotide; adenyl ribonucleotide; aryl sulfide; organochlorine compound	protein kinase agonist
zofenopril zofenopril: structure given in first source; SQ 26900 refers to K salt & SQ 26991 to Ca salt. zofenopril : A proline derivative that is 4-(phenylsulfanyl)-L-proline in which the amine proton is replaced by a (2S)-3-(benzoylsulfanyl)-2-methylpropanoyl group. A prodrug for zofenoprilat.	3.15	1	0	aryl sulfide; L-proline derivative; N-acyl-L-amino acid; thioester	anticonvulsant; apoptosis inhibitor; cardioprotective agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; prodrug; vasodilator agent
lopinavir [no description available]	3.85	3	0	amphetamines; dicarboxylic acid diamide	anticoronaviral agent; antiviral drug; HIV protease inhibitor
cholanic acid [no description available]	2.04	1	0	5beta-cholanic acids; cholanic acid
5-alpha-dihydroprogesterone 5-alpha-Dihydroprogesterone: A biologically active 5-alpha-reduced metabolite of plasma PROGESTERONE. It is the immediate precursor of 5-alpha-pregnan-3-alpha-ol-20-one (ALLOPREGNANOLONE), a neuroactive steroid that binds with GABA(A) RECEPTOR.. 5alpha-pregnane-3,20-dione : A C21-steroid hormone that is 5alpha-pregnane substituted by oxo groups at positions 3 and 20. It is a metabolite of progestrone.	2.04	1	0	20-oxo steroid; 3-oxo-5alpha-steroid; C21-steroid hormone	human metabolite; progestogen
melezitose melezitose: structure. melezitose : A trisaccharide produced by insects such as aphids.	2.03	1	0	trisaccharide	animal metabolite
glycyltyrosine Gly-Tyr : A dipeptide composed of glycine and L-tyrosine joined by a peptide linkage.	2.37	2	0	dipeptide	metabolite
methyl lithocholate methyl lithocholate: RN given refers to (3alpha,5beta)-isomer	2.04	1	0
glycidyl nitrate glycidyl nitrate: a nitric oxide donor; structure in first source. peptidoglycan : A peptidoglycosaminoglycan formed by alternating residues of beta-(1->4)-linked N-acetylglucosamine and N-acetylmuramic acid {2-amino-3-O-[(S)-1-carboxyethyl]-2-deoxy-D-glucose} residues. Attached to the carboxy group of the muramic acid is a peptide chain of three to five amino acids.	1.95	1	0
glycylsarcosine glycylsarcosine : A dipeptide obtained by formal condensation of the carboxy group of glycine with the amino group of sarcosine.	3.56	2	0	dipeptide zwitterion; dipeptide
4-methylumbelliferyl-galactopyranoside 4-methylumbelliferyl-galactopyranoside: fluorogenic substrate; RN given refers to (beta-D)-isomer. 4-methylumbelliferyl beta-D-galactoside : A beta-D-galactoside having a 4-methylumbelliferyl substituent at the anomeric position.	1.96	1	0	beta-D-galactoside; coumarins; monosaccharide derivative	chromogenic compound
glucuronic acid Glucuronic Acid: A sugar acid formed by the oxidation of the C-6 carbon of GLUCOSE. In addition to being a key intermediate metabolite of the uronic acid pathway, glucuronic acid also plays a role in the detoxification of certain drugs and toxins by conjugating with them to form GLUCURONIDES.. D-glucuronic acid : The D-enantiomer of glucuronic acid.. D-glucopyranuronic acid : A D-glucuronic acid in cyclic pyranose form.	2.47	2	0	D-glucuronic acid	algal metabolite
s-(2,4-dinitrophenyl)glutathione S-(2,4-dinitrophenyl)glutathione : A glutathione conjugate in which the thiol hydrogen of glutathione has been replaced by a 2,4-dinitrophenyl group.	4.59	8	0	glutathione conjugate
diosgenin [no description available]	2.69	3	0	3beta-sterol; hexacyclic triterpenoid; sapogenin; spiroketal	antineoplastic agent; antiviral agent; apoptosis inducer; metabolite
sporidesmin sporidesmin: RN given refers to sporidesmin; structure. sporidesmin A : An organic heteropentacyclic compound that has formula C18H20ClN3O6S2, produced by the saprophyte fungus Pithomyces chartarum. It is a mycotoxin responsible for the hepatogenous photosensitisation disease facial eczema in ruminants.	1.96	1	0	aromatic ether; cyclic ketone; diketone; organic disulfide; organic heteropentacyclic compound; organochlorine compound; secondary alcohol; tertiary alcohol; tertiary amino compound	mycotoxin; Wnt signalling activator
coumarin 6 coumarin 6: structure in first source	2.13	1	0	7-aminocoumarins	fluorochrome
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.	2.05	1	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.	2.02	1	0	17beta-hydroxy steroid; 3-hydroxy steroid; organofluorine compound; sulfoxide	antineoplastic agent; estrogen antagonist; estrogen receptor antagonist
enkephalin, d-penicillamine (2,5)- Enkephalin, D-Penicillamine (2,5)-: A disulfide opioid pentapeptide that selectively binds to the DELTA OPIOID RECEPTOR. It possesses antinociceptive activity.. DPDPE : A heterodetic cyclic peptide that is a cyclic enkephalin analogue, having D-penicillaminyl residues located at positions 2 and 5, which form the heterocycle via a disulfide bond.	2.75	3	0	heterodetic cyclic peptide	delta-opioid receptor agonist
imipenem, anhydrous Imipenem: Semisynthetic thienamycin that has a wide spectrum of antibacterial activity against gram-negative and gram-positive aerobic and anaerobic bacteria, including many multiresistant strains. It is stable to beta-lactamases. Clinical studies have demonstrated high efficacy in the treatment of infections of various body systems. Its effectiveness is enhanced when it is administered in combination with CILASTATIN, a renal dipeptidase inhibitor.. imipenem : A broad-spectrum, intravenous beta-lactam antibiotic of the carbapenem subgroup.	2.71	3	0	beta-lactam antibiotic allergen; carbapenems; zwitterion	antibacterial drug
cremophor el cremophor EL: solvent for Althesin & Propanidid implicated as possible cause of similar adverse effects polyethoxylated castor oil; RN given refers to cpd with unknown MF; see also records for cremophor & cremophor A	2.07	1	0
quin2 Quin2: fluorescent highly selective Ca indicator, binding Ca 1:1; structure given in first source	1.97	1	0
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.	2.01	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.	3.74	10	0	primary alcohol; pyrimidines; sulfonamide	antihypertensive agent; endothelin receptor antagonist
fluo-3 Fluo-3: fluorescent Ca(2+) indicator; permits continuous monitoring of Ca without interference with use of UV-sensitive caged compounds	2.46	2	0	xanthene dye	fluorochrome
fpl 55712 FPL 55712: inhibitor of SRS-A and LTC4 and LTD4 receptors	2.67	3	0	aromatic ketone
paxilline paxilline: structure given in first source; RN given refers to (2R-(2alpha,4bbeta,6aalpha,12bbeta,12calpha,14abeta))-isomer. paxilline : An indole diterpene alkaloid with formula C27H33NO4 isolated from Penicillium paxilli. It is a potent inhibitor of large conductance Ca2(+)- and voltage-activated K(+) (BK)-type channels.	2.1	1	0	diterpene alkaloid; enone; organic heterohexacyclic compound; terpenoid indole alkaloid; tertiary alcohol	anticonvulsant; Aspergillus metabolite; EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor; genotoxin; geroprotector; mycotoxin; Penicillium metabolite; potassium channel blocker
beauvericin beauvericin: 18-membered cyclodepsipeptides. beauvericin : A trimeric cyclodepsipeptide composed from alternating methylphenylalanyl and hydroxyvaleryl residues.	2	1	0
artesunic acid [no description available]	2.13	1	0
indobufen indobufen: thromboxane A2 antagonist	2.06	1	0	isoindoles
s-ethyl glutathione [no description available]	2.39	2	0	oligopeptide
3-((3-cholamidopropyl)dimethylammonium)-1-propanesulfonate 3-((3-cholamidopropyl)dimethylammonium)-1-propanesulfonate: a surfactant; structure given in first source	3.25	6	0	1,1-diunsubstituted alkanesulfonate
perindopril Perindopril: An angiotensin-converting enzyme inhibitor. It is used in patients with hypertension and heart failure.. perindopril : An alpha-amino acid ester that is the ethyl ester of N-{(2S)-1-[(2S,3aS,7aS)-2-carboxyoctahydro-1H-indol-1-yl]-1-oxopropan-2-yl}-L-norvaline	1.98	1	0	alpha-amino acid ester; dicarboxylic acid monoester; ethyl ester; organic heterobicyclic compound	antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor
(2-(trimethylammonium)ethyl)methanethiosulfonate (2-(trimethylammonium)ethyl)methanethiosulfonate: RN given for bromide; used in dopamine analysis	2.41	2	0
fingolimod hydrochloride Fingolimod Hydrochloride: A sphingosine-derivative and IMMUNOSUPPRESSIVE AGENT that blocks the migration and homing of LYMPHOCYTES to the CENTRAL NERVOUS SYSTEM through its action on SPHINGOSINE 1-PHOSPHATE RECEPTORS. It is used in the treatment of MULTIPLE SCLEROSIS.. fingolimod hydrochloride : The hydrochloride salt of 2-amino-2-[2-(4-octylphenyl) ethyl]-1,3-propanediol (fingolimod).	2.07	1	0	hydrochloride	immunosuppressive agent; prodrug; sphingosine-1-phosphate receptor agonist
benzamil [no description available]	2.31	1	0	guanidines; pyrazines
1-hexadecyl-2-acetyl-glycero-3-phosphocholine Platelet Activating Factor: A phospholipid derivative formed by PLATELETS; BASOPHILS; NEUTROPHILS; MONOCYTES; and MACROPHAGES. It is a potent platelet aggregating agent and inducer of systemic anaphylactic symptoms, including HYPOTENSION; THROMBOCYTOPENIA; NEUTROPENIA; and BRONCHOCONSTRICTION.. 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine : A 2-acetyl-1-alkyl-sn-glycero-3-phosphocholine betaine which has hexadecyl as the alkyl group. PAF is a potent phospholipid activator and mediator of many leukocyte functions, including platelet aggregation, inflammation, and anaphylaxis.	3.79	11	0	2-acetyl-1-alkyl-sn-glycero-3-phosphocholine	antihypertensive agent; beta-adrenergic antagonist; bronchoconstrictor agent; hematologic agent; vasodilator agent
testosterone 17-glucosiduronate testosterone glucuronate: natural conjugate isolated from human plasma; RN given refers to (beta)-isomer. testosterone 17-glucosiduronic acid : A steroid glucosiduronic that is testosterone carrying a glucosiduronic acid residue at position 17.	2.38	2	0	3-oxo steroid; beta-D-glucosiduronic acid; enone; steroid glucosiduronic acid	human metabolite
deoxyglucose Deoxyglucose: 2-Deoxy-D-arabino-hexose. An antimetabolite of glucose with antiviral activity.. deoxyglucose : A deoxyhexose comprising glucose having at least one hydroxy group replaced by hydrogen.	1.96	1	0
beta-lumicolchicine Lumicolchicines: Three, alpha, beta, and gamma isomers of ultraviolet degradation products of colchicine that lack many of the physiological actions of the parent; used as experimental control for colchicine actions.	2.68	3	0
precirol precirol: octadecanoic acid esters; 2,3-dihydroxypropyl ester mixed with 3-hydroxy-2-((1-oxohexadecyl)oxy)propyl octadienoate & 2-((1-oxohexadecyl)oxy)-1,3-propanediol; auxiliary in tableting; alpha glycerol palmitostearate	2.13	1	0
valerates Valerates: Derivatives of valeric acid, including its salts and esters.	1.95	1	0	short-chain fatty acid anion; straight-chain saturated fatty acid anion	plant metabolite
desmethylphalloin desmethylphalloin: cyclopeptide similar to phalloidin	2.01	1	0
thromboxanes thromboxane : A class of oxygenated oxane derivatives, originally derived from prostaglandin precursors in platelets, that stimulate aggregation of platelets and constriction of blood vessels.	2.37	2	0
dodecyl-beta-d-maltoside dodecyl beta-D-maltoside : A glycoside resulting from attachment of a dodecyl group to the reducing-end anomeric centre of a beta-maltose molecule.	3.15	1	0	disaccharide derivative; glycoside	detergent
tanshinone tanshinone: from root of Salvia miltiorrhiza Bunge; RN given refers to tanshinone I; cardioprotective agent and neuroprotective agent	2.11	1	0	abietane diterpenoid	anticoronaviral agent
epomediol epomediol: marked choleretic activity in Wistar rats; mechanism of action may be related to increases in both the bile salt dependent & independent fractions of bile	6.96	1	0	oxanes
dihydro-dids [no description available]	1.96	1	0
glycolithocholic acid glycolithocholic acid: RN given refers to (3alpha,5beta)-isomer. glycolithocholic acid : The glycine conjugate of lithocholic acid.	3.49	8	0	bile acid glycine conjugate; N-acylglycine
estrone-3-glucuronide [no description available]	1.99	1	0	17-oxo steroid; beta-D-glucosiduronic acid; steroid glucosiduronic acid	human metabolite; mouse metabolite
s-methyl glutathione [no description available]	2.01	1	0	methyl sulfide; S-substituted glutathione; zwitterion
2-aminobicyclo(2,2,1)heptane-2-carboxylic acid 2-aminobicyclo(2,2,1)heptane-2-carboxylic acid: amino acid analog; releases insulin; RN given refers to unlabeled cpd without isomeric designation	2.37	2	0	monoterpenoid
glycyl-arginyl-glycyl-aspartyl-seryl-proline glycyl-arginyl-glycyl-aspartyl-seryl-proline: can duplicate the binding activity of fibronectin vitronectin; RN given refers to ALL-L isomer	2.08	1	0
taurohyodeoxycholic acid taurohyodeoxycholic acid: a biliary acid used for the prevention and therapy of gallstones and related symptoms	3.27	6	0	bile acid taurine conjugate
elacridar Elacridar: inhibitor of MDR1 PROTEIN; structure given in first source	3.14	5	0
caprylates Caprylates: Derivatives of caprylic acid. Included under this heading are a broad variety of acid forms, salts, esters, and amides that contain a carboxy terminated eight carbon aliphatic structure.. octanoate : A straight-chain saturated fatty acid anion that is the conjugate base of octanoic acid (caprylic acid); believed to block adipogenesis.	3.2	6	0	fatty acid anion 8:0; straight-chain saturated fatty acid anion	human metabolite; Saccharomyces cerevisiae metabolite
tauroglycocholic acid tauroglycocholic acid: RN given refers to cpd with unknown MF	3.37	7	0
muricholic acid muricholic acid: internal standard in analysis of fecal bile acids; RN given refers to (3 alpha,5 beta)-isomer	3.39	7	0	3alpha-hydroxy steroid; 6-hydroxy steroid; 7-hydroxy steroid; bile acid; C24-steroid; trihydroxy-5beta-cholanic acid
pramipexole Pramipexole: A benzothiazole derivative and dopamine agonist with antioxidant properties that is used in the treatment of PARKINSON DISEASE and RESTLESS LEGS SYNDROME.. pramipexole : A member of the class of benzothiazoles that is 4,5,6,7-tetrahydro-1,3-benzothiazole in which the hydrogens at the 2 and 6-pro-S-positions are substituted by amino and propylamino groups, respectively.	3.15	1	0	benzothiazoles; diamine	antidyskinesia agent; antiparkinson drug; dopamine agonist; radical scavenger
valdecoxib [no description available]	2.05	1	0	isoxazoles; sulfonamide	antipyretic; antirheumatic drug; cyclooxygenase 2 inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
parecoxib parecoxib: structure in first source. parecoxib : An N-acylsulfonamide resulting from the formal condensation of valdecoxib with propionic acid. It is a prodrug for valdecoxib.	2.03	1	0	isoxazoles; N-sulfonylcarboxamide	cyclooxygenase 2 inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; prodrug
carboxypolymethylene carbomer: high molecular polyanionic substance	2.1	1	0
fpl-52694 FPL-52694: mast cell stabilizer; RN given refers to parent cpd; FPL-52694 is mono-Na salt; structure given in first source	1.99	1	0
6-bromoconduritol [no description available]	1.98	1	0
gadolinium 1,4,7,10-tetraazacyclododecane-n,n',n'',n'''-tetraacetate gadolinium 1,4,7,10-tetraazacyclododecane-N,N',N'',N'''-tetraacetate: RN refers to Na salt	2.03	1	0
sulforhodamine 101 [no description available]	2.21	1	0	organic heteroheptacyclic compound	fluorochrome
estriol-16 alpha-glucuronide [no description available]	2.01	1	0	17beta-hydroxy steroid; 3-hydroxy steroid; beta-D-glucosiduronic acid; phenols; steroid glucosiduronic acid	human urinary metabolite
3,7,12-trihydroxycholestan-26-oic acid 3,7,12-trihydroxycholestan-26-oic acid: RN given refers to (3alpha,5beta,7alpha,12alpha)-isomer. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oic acid : A steroid acid that is 5beta-cholestan-26-oic acid which is substituted by hydroxy groups as the 3alpha, 7alpha, and 12alpha positions.	1.99	1	0	12alpha-hydroxy steroid; 3alpha-hydroxy steroid; 7alpha-hydroxy steroid; hydroxy monocarboxylic acid; steroid acid	human metabolite
ursocholic acid ursocholic acid: see also records for allocholic and cholic acids. ursocholic acid : A bile acid that is 5beta-cholan-24-oic acid bearing three hydroxy substituents at positions 3alpha, 7beta and 12alpha.	4.07	3	1	12alpha-hydroxy steroid; 3alpha-hydroxy steroid; 7beta-hydroxy steroid; bile acid; C24-steroid; trihydroxy-5beta-cholanic acid	EC 1.1.1.159 (7alpha-hydroxysteroid dehydrogenase) inhibitor; human urinary metabolite
celastrol [no description available]	2.15	1	0	monocarboxylic acid; pentacyclic triterpenoid	anti-inflammatory drug; antineoplastic agent; antioxidant; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; Hsp90 inhibitor; metabolite
imatinib mesylate imatinib methanesulfonate : A methanesulfonate (mesylate) salt that is the monomesylate salt of imatinib. Used for treatment of chronic myelogenous leukemia and gastrointestinal stromal tumours.	2.49	2	0	methanesulfonate salt	anticoronaviral agent; antineoplastic agent; apoptosis inducer; tyrosine kinase inhibitor
gefitinib [no description available]	2.04	1	0	aromatic ether; monochlorobenzenes; monofluorobenzenes; morpholines; quinazolines; secondary amino compound; tertiary amino compound	antineoplastic agent; epidermal growth factor receptor antagonist
n(6)-(3-iodobenzyl)-5'-n-methylcarboxamidoadenosine N(6)-(3-iodobenzyl)-5'-N-methylcarboxamidoadenosine: structure given in first source; a selective A(3) adenosine receptor agonist. 3-iodobenzyl-5'-N-methylcarboxamidoadenosine : A derivative of adenosine in which the 5'-hydroxymethyl group is replaced by N-ethylcarboxamido and one of the hydrogens of the exocyclic amino function is substituted by a 3-iodobenzyl group.	2.44	2	0	adenosines; monocarboxylic acid amide; organoiodine compound	adenosine A3 receptor agonist
tyrosyl-glycyl-glycine tyrosyl-glycyl-glycine: RN given refers to L-isomer; this may not be the same as IMREG-1. Tyr-Gly-Gly : A tripeptide composed of one L-tyrosine and two glycine residues joined in sequence.	2.01	1	0	tripeptide zwitterion; tripeptide	metabolite
7 alpha-hydroxy-4-cholesten-3-one 7 alpha-hydroxy-4-cholesten-3-one: structure. 7alpha-hydroxycholest-4-en-3-one : A cholestanoid consisting of a cholesterol core having an oxo group at the 3-position, a C=C bond at the 4,5-position and an alpha-hydroxy group at the 7-position.	7.4	10	0	3-oxo-Delta(4) steroid; 7alpha-hydroxy steroid; cholestanoid	human metabolite; mouse metabolite
2-chloro-n(6)cyclopentyladenosine 2-chloro-N(6)cyclopentyladenosine: highly selective agonist at A1 adenosine receptors	2	1	0
23-seleno-25-homotaurocholic acid [no description available]	19.52	133	6	corticosteroid hormone
n-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)phosphatidylethanolamine N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)phosphatidylethanolamine: fluorescent probe for membrane lipids	2.38	2	0
3-tyr-octreotide 3-Tyr-octreotide: cyclic octapeptide analog of somatostatin; potent somatostatin agonist; RN given refers to (R-(R,R))-isomer; RN for cpd without isomeric designation not avail 3/90	1.99	1	0
rmi 12330a RMI 12330A: adenyl cyclase inhibitor in rat liver; RN given refers to (cis)-isomer; NM refers to HCl, (cis)-isomer; structure	2.06	1	0
solutol hs 15 Solutol HS 15: multidrug resistance modification agent in tumor cells; polyoxyethylene esters of 12-hydroxystearic acid; previous RN 105109-85-1	2.07	1	0	aliphatic alcohol
glycerophosphoinositol 4,5-bisphosphate glycerophosphoinositol 4,5-bisphosphate: do not confuse with phosphatidylinositols which have fatty acids esterified at the C-1 and C-2 hydroxyl groups of glycerol	1.98	1	0
6-hexadecanoylamino-4-methylumbelliferyl-galactopyranoside 6-hexadecanoylamino-4-methylumbelliferyl-galactopyranoside: structure given in first source	1.98	1	0
lithocholate 3-o-glucuronide lithocholate 3-O-glucuronide: structure in first source	2.67	3	0
methotrexate [no description available]	5.79	28	0	dicarboxylic acid; monocarboxylic acid amide; pteridines	abortifacient; antimetabolite; antineoplastic agent; antirheumatic drug; dermatologic drug; DNA synthesis inhibitor; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; immunosuppressive agent
ono 3307 ONO 3307: RN given refers to parent cpd; structure given in first source	1.98	1	0
fpl 67047xx FPL 67047XX: inhibits phospholipase A2; structure in first source	1.99	1	0
s(alpha)-methyl-6-(2-quinolinylmethoxy)-2-naphthaleneacetic acid S(alpha)-methyl-6-(2-quinolinylmethoxy)-2-naphthaleneacetic acid: inhibitor of leukotriene-mediated reactions; structure in first source; WY-50295K is the tromethamine salt	1.98	1	0
olmesartan medoxomil Olmesartan Medoxomil: An ANGIOTENSIN II TYPE 1 RECEPTOR BLOCKER that is used to manage HYPERTENSION.	2.45	2	0	biphenyls
5-carboxyfluorescein diacetate [no description available]	2.46	2	0
xylose xylopyranose: structure in first source	2.65	3	0	D-xylose
beta-lactams 2-azetidinone: structure in first source. azetidin-2-one : An unsubstituted beta-lactam compound.. beta-lactam : A lactam in which the amide bond is contained within a four-membered ring, which includes the amide nitrogen and the carbonyl carbon.	2.21	1	0	beta-lactam antibiotic allergen; beta-lactam
proline Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.	3.25	6	0	amino acid zwitterion; glutamine family amino acid; L-alpha-amino acid; proline; proteinogenic amino acid	algal metabolite; compatible osmolytes; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
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.	2.49	2	0	secondary alpha-hydroxy ketone; tetracyclic diterpenoid	antimalarial; antineoplastic agent; photosensitizing agent
atazanavir atazanavir : A heavily substituted carbohydrazide that is an antiretroviral drug of the protease inhibitor (PI) class used to treat infection of human immunodeficiency virus (HIV).	2.07	1	0	carbohydrazide	antiviral drug; HIV protease inhibitor
tariquidar [no description available]	3.15	1	0	benzamides
levofloxacin Levofloxacin: The L-isomer of Ofloxacin.. levofloxacin : An optically active form of ofloxacin having (S)-configuration; an inhibitor of bacterial topoisomerase IV and DNA gyrase.	3.15	1	0	9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid; fluoroquinolone antibiotic; quinolone antibiotic	antibacterial drug; DNA synthesis inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; topoisomerase IV inhibitor
ezetimibe Ezetimibe: An azetidine derivative and ANTICHOLESTEREMIC AGENT that inhibits intestinal STEROL absorption. It is used to reduce total CHOLESTEROL; LDL CHOLESTEROL, and APOLIPOPROTEINS B in the treatment of HYPERLIPIDEMIAS.. ezetimibe : A beta-lactam that is azetidin-2-one which is substituted at 1, 3, and 4 by p-fluorophenyl, 3-(p-fluorophenyl)-3-hydroxypropyl, and 4-hydroxyphenyl groups, respectively (the 3R,3'S,4S enantiomer).	4.4	6	0	azetidines; beta-lactam; organofluorine compound	anticholesteremic drug; antilipemic drug; antimetabolite
silybin dihemisuccinate [no description available]	1.96	1	0
tezosentan tezosentan: structure in first source	2.01	1	0
estriol glucuronide [no description available]	1.96	1	0
s 8921 S 8921: inhibits bile acid transport; structure given in first source	2.41	2	0
varespladib [no description available]	2	1	0	aromatic ether; benzenes; dicarboxylic acid monoamide; indoles; monocarboxylic acid; primary carboxamide	anti-inflammatory drug; antidote; EC 3.1.1.4 (phospholipase A2) inhibitor
disopyramide, (s)-isomer [no description available]	2.04	1	0
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.	2.73	3	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
norcholate norcholic acid: found in urine of patients with liver cirrhosis	2.38	2	0	bile acid
olmesartan olmesartan: an active metabolite of CS 866	3.15	1	0	biphenylyltetrazole	angiotensin receptor antagonist; antihypertensive agent
androsterone sulfate androsterone sulfate: RN given refers to (3alpha,5alpha)-isomer. androsterone sulfate : A steroid sulfate that is the 3-sulfate of androsterone.	1.99	1	0	17-oxo steroid; androstanoid; steroid sulfate	human metabolite; mouse metabolite
clofibride clofibride: structure	1.95	1	0	monocarboxylic acid
3,7,12-trihydroxycoprostane 3,7,12-trihydroxycoprostane: intermediate in bile acid synthesis in liver; enhances rate of porphyrin synthesis in cultured liver cells by induction of delta-aminolevulinic acid synthetase; RN given refers to (3alpha,5beta,7alpha,12alpha)-isomer; structure	1.99	1	0	12alpha-hydroxy steroid; 3alpha-hydroxy steroid; 7alpha-hydroxy steroid	human metabolite; mouse metabolite
4-acetylaminohippuric acid [no description available]	1.95	1	0
zinc hematoporphyrin [no description available]	2.15	1	0
3-doxylcholestane 3-doxylcholestane: RN given refers to (5alpha)-isomer; structure	1.98	1	0
(sulfobromophthalein)glutathione conjugate [no description available]	2	1	0
calcium pyrophosphate [no description available]	2.38	2	0
tetraphenylphosphonium tetraphenylphosphonium: RN given refers to parent cpd; structure. tetraphenylphosphonium : A polyatomic cation consisting of four phenyl groups attached to a central phosphonium.	1.98	1	0	heteroorganic entity; phosphorus molecular entity; polyatomic cation
scymnol scymnol: structure given in first source	2	1	0	12alpha-hydroxy steroid; 24-hydroxy steroid; 26-hydroxy steroid; 27-hydroxy steroid; 3alpha-hydroxy steroid; 7alpha-hydroxy steroid
technetium tc 99m pentetate Technetium Tc 99m Pentetate: A technetium imaging agent used in renal scintigraphy, computed tomography, lung ventilation imaging, gastrointestinal scintigraphy, and many other procedures which employ radionuclide imaging agents.	2.03	1	0
procaine amide ethobromide procaine amide ethobromide: RN given refers to parent cpd	1.98	1	0
aminopterin Aminopterin: A folic acid derivative used as a rodenticide that has been shown to be teratogenic.	2	1	0	dicarboxylic acid	EC 1.5.1.3 (dihydrofolate reductase) inhibitor; mutagen
17 alpha-hydroxyprogesterone caproate 17 alpha-Hydroxyprogesterone Caproate: Hydroxyprogesterone derivative that acts as a PROGESTIN and is used to reduce the risk of recurrent MISCARRIAGE and of PREMATURE BIRTH. It is also used in combination with ESTROGEN in the management of MENSTRUATION DISORDERS.	2.49	2	0	corticosteroid hormone
varenicline Varenicline: A benzazepine derivative that functions as an ALPHA4-BETA2 NICOTINIC RECEPTOR partial agonist. It is used for SMOKING CESSATION.. varenicline : An organic heterotetracyclic compound that acts as a partial agonist for nicotinic cholinergic receptors and is used (in the form of its tartate salt) as an aid to giving up smoking.	3.57	2	0
angiotensin ii Giapreza: injectable form of angiotensin II used to increase blood pressure in adult patients with septic or other distributive shock. Ile(5)-angiotensin II : An angiotensin II that acts on the central nervous system (PDB entry: 1N9V).	3.12	5	0	amino acid zwitterion; angiotensin II	human metabolite
campesterol campesterol: RN refers to (3beta,24R)-isomer; structure	2.42	2	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; C28-steroid; phytosterols	mouse metabolite
atropine tropan-3alpha-yl 3-hydroxy-2-phenylpropanoate : A tropane alkaloid that is (1R,5)-8-methyl-8-azabicyclo[3.2.1]octane substituted by a (3-hydroxy-2-phenylpropanoyl)oxy group at position 3.	3.58	9	0
lignin Lignin: The most abundant natural aromatic organic polymer found in all vascular plants. Lignin together with cellulose and hemicellulose are the major cell wall components of the fibers of all wood and grass species. Lignin is composed of coniferyl, p-coumaryl, and sinapyl alcohols in varying ratios in different plant species. (From Merck Index, 11th ed). lignin : A polyphenylpropanoid derived from three monolignol monomers: trans-p-coumaryl alcohol, coniferol and trans-sinapyl alcohol. There is extensive cross-linking and no defined primary structure.	3.75	2	1
kw 5805 KW 5805: structure given in first source; RN given refers to (+)-isomer	1.98	1	0
sb 203580 [no description available]	2.46	2	0	imidazoles; monofluorobenzenes; pyridines; sulfoxide	EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector; Hsp90 inhibitor; neuroprotective agent
zm 241385 ZM 241385: a high affinity radioligand selective for the A2a adenosine receptor	2.03	1	0	diamino-1,3,5-triazine
erlotinib [no description available]	2.46	2	0	aromatic ether; quinazolines; secondary amino compound; terminal acetylenic compound	antineoplastic agent; epidermal growth factor receptor antagonist; protein kinase inhibitor
cilengitide Cilengitide: an alphaVbeta3 integrin antagonist that paralyzes cancer cells	2	1	0	oligopeptide
lu 135252 [no description available]	2.44	2	0
organophosphonates hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.	2	1	0	divalent inorganic anion; phosphite ion
l 158809 L 158809: RN & structure given in first source; angiotensin receptor antagonist	2.05	1	0
7-aminocoumarin 7-amino coumarin: structure in first source	2.02	1	0
24-norursodeoxycholic acid 24-norursodeoxycholic acid: structure given in first source	2.45	2	0
corticosterone sulfate [no description available]	1.99	1	0
troleandomycin Troleandomycin: A macrolide antibiotic that is similar to ERYTHROMYCIN.. troleandomycin : A semi-synthetic macrolide antibiotic obtained by acetylation of the three free hydroxy groups of oleandomycin. Troleandomycin is only found in individuals that have taken the drug.	1.96	1	0	acetate ester; epoxide; macrolide antibiotic; monosaccharide derivative; polyketide; semisynthetic derivative	EC 1.14.13.97 (taurochenodeoxycholate 6alpha-hydroxylase) inhibitor; xenobiotic
tbc-11251 sitaxsentan: endothelin A receptor antagonist; structure in first source	2.48	2	0	benzodioxoles
tolvaptan [no description available]	2.13	1	0	benzazepine; benzenedicarboxamide	aquaretic; vasopressin receptor antagonist
sorafenib [no description available]	2.31	1	0	(trifluoromethyl)benzenes; aromatic ether; monochlorobenzenes; phenylureas; pyridinecarboxamide	angiogenesis inhibitor; anticoronaviral agent; antineoplastic agent; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; ferroptosis inducer; tyrosine kinase inhibitor
demecolcine Demecolcine: An alkaloid isolated from Colchicum autumnale L. and used as an antineoplastic.. (-)-demecolcine : A secondary amino compound that is (S)-colchicine in which the N-acetyl group is replaced by an N-methyl group. Isolable from the autumn crocus, Colchicum autumnale, it is less toxic than colchicine and is used as an antineoplastic.	1.98	1	0	alkaloid; secondary amino compound	antineoplastic agent; microtubule-destabilising agent
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.	6.05	115	0	12alpha-hydroxy steroid; 3alpha-hydroxy steroid; 7alpha-hydroxy steroid; bile acid; C24-steroid; trihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
cymarine Cymarine: A cardiotonic cardiac glycoside found in STROPHANTHUS. The aglycone is STROPHANTHIN.	1.95	1	0
erythritol [no description available]	4.87	36	0	butane-1,2,3,4-tetrol	antioxidant; human metabolite; plant 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.	10.15	204	2	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human blood serum metabolite
cortisone [no description available]	2.06	1	0	11-oxo steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	human metabolite; mouse metabolite
Deoxycholic acid methyl ester [no description available]	2.05	1	0	cholanoid
3-nitrotyrosine 3-nitrotyrosine: RN given refers to parent cpd without isomeric designation. 3-nitrotyrosine : A nitrotyrosine comprising tyrosine having a nitro group at the 3-position on the phenyl ring.	2.11	1	0	2-nitrophenols; C-nitro compound; nitrotyrosine; non-proteinogenic alpha-amino acid
stigmastanol stigmastanol: saturated analog of beta-sitosterol; RN given refers to (3beta,5alpha)-isomer. stigmastanol : A 3-hydroxy steroid that is 5alpha-stigmastane which is substituted at the 3beta position by a hydroxy group.	2.04	1	0	3-hydroxy steroid; phytosterols	anticholesteremic drug; plant metabolite
gamma-lumicolchicine [no description available]	2.39	2	0	acetamides; alkaloid; carbotricyclic compound
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.	2.04	1	0	17-oxo steroid; 3beta-hydroxy steroid; androstanoid	androgen; animal metabolite; human blood serum metabolite; mouse metabolite; rat metabolite
corticosterone acetate [no description available]	1.96	1	0	corticosteroid hormone
noscapine Noscapine: A naturally occurring opium alkaloid that is a centrally acting antitussive agent.. (-)-noscapine : A benzylisoquinoline alkaloid that is 1,2,3,4-tetrahydroisoquinoline which is substituted by a 4,5-dimethoxy-3-oxo-1,3-dihydro-2-benzofuran-1-yl group at position 1, a methylenedioxy group at positions 6-7 and a methoxy group at position 8. Obtained from plants of the Papaveraceae family, it lacks significant painkilling properties and is primarily used for its antitussive (cough-suppressing) effects.	2.04	1	0	aromatic ether; benzylisoquinoline alkaloid; cyclic acetal; isobenzofuranone; organic heterobicyclic compound; organic heterotricyclic compound; tertiary amino compound	antineoplastic agent; antitussive; apoptosis inducer; plant metabolite
acivicin [no description available]	2.37	2	0	isoxazoles; non-proteinogenic L-alpha-amino acid; organochlorine compound	antileishmanial agent; antimetabolite; antimicrobial agent; antineoplastic agent; EC 2.3.2.2 (gamma-glutamyltransferase) inhibitor; glutamine antagonist; metabolite
wortmannin [no description available]	3.51	8	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
taurochenodeoxycholic acid Taurochenodeoxycholic Acid: A bile salt formed in the liver by conjugation of chenodeoxycholate with taurine, usually as the sodium salt. It acts as detergent to solubilize fats in the small intestine and is itself absorbed. It is used as a cholagogue and choleretic.. taurochenodeoxycholate : An organosulfonate oxoanion that is the conjugate base of taurochenodeoxycholic acid arising from deprotonation of the sulfonate OH group; major species at pH 7.3.. taurochenodeoxycholic acid : A bile acid taurine conjugate of chenodeoxycholic acid.	8.84	158	1	bile acid taurine conjugate	human metabolite; mouse metabolite
bortezomib [no description available]	2.17	1	0	amino acid amide; L-phenylalanine derivative; pyrazines	antineoplastic agent; antiprotozoal drug; protease inhibitor; proteasome inhibitor
calcein am calcein AM: a non-fluorescent compound cleaved to a fluorescent compound by non-specific intracellular esterases. calcein am : An organic heteropentacyclic compound that is calcein in which all four carboxy group hydrogens have been substituted by (acetyloxy)methoxy groups and the hyrodgens of the two hydroxy groups have been substituted by acetyl groups. It is a a non-fluorescent probe cleaved to a fluorescent probe by non-specific intracellular esterases.	2.08	1	0	2-benzofurans; acetate ester; gamma-lactone; organic heteropentacyclic compound; oxaspiro compound; xanthene dye	fluorochrome
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.	4.93	6	0	1,3-thiazoles; carbamate ester; carboxamide; L-valine derivative; ureas	antiviral drug; environmental contaminant; HIV protease inhibitor; xenobiotic
tryptoquivaline fumitremorgin C : An organic heteropentacyclic compound that is a mycotoxic indole alkaloid produced by several fungi. A potent and specific inhibitor of the breast cancer resistance protein multidrug transporter.	3.53	2	0	aromatic ether; indole alkaloid; organic heteropentacyclic compound	breast cancer resistance protein inhibitor; mycotoxin
dihydropyridines Dihydropyridines: Pyridine moieties which are partially saturated by the addition of two hydrogen atoms in any position.	2.41	2	0
leupeptins Leupeptins: A group of acylated oligopeptides produced by Actinomycetes that function as protease inhibitors. They have been known to inhibit to varying degrees trypsin, plasmin, KALLIKREINS, papain and the cathepsins.	2.93	4	0
lithium chloride Lithium Chloride: A salt of lithium that has been used experimentally as an immunomodulator.. lithium chloride : A metal chloride salt with a Li(+) counterion.	2.01	1	0	inorganic chloride; lithium salt	antimanic drug; geroprotector
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.	2.65	3	0
dithiothreitol [no description available]	2.04	1	0	1,4-dithiothreitol
bradykinin [no description available]	2.68	3	0	oligopeptide	human blood serum metabolite; vasodilator agent
glucosamine D-glucosamine : An amino sugar whose structure comprises D-glucose having an amino substituent at position 2.. 2-amino-2-deoxy-D-glucopyranose : A D-glucosamine whose structure comprises D-glucopyranose having an amino substituent at position 2.	1.97	1	0	D-glucosamine	Escherichia coli metabolite; geroprotector; mouse metabolite
elastin [no description available]	2.66	3	0	oligopeptide
mevalonic acid Mevalonic Acid: A dihydroxy monocarboxylic acid and precursor in the biosynthetic pathway known as the mevalonate pathway, which produces terpenes and steroids that are vital for diverse cellular functions.. mevalonic acid : A racemate composed of equimolar amounts of (R)- and (S)-mevalonic acid.. (R)-mevalonic acid : The (R)-enantiomer of mevalonic acid.	3.47	8	0	3,5-dihydroxy-3-methylpentanoic acid
raffinose Raffinose: A trisaccharide occurring in Australian manna (from Eucalyptus spp, Myrtaceae) and in cottonseed meal.. raffinose : A trisaccharide composed of alpha-D-galactopyranose, alpha-D-glucopyranose and beta-D-fructofuranose joined in sequence by 1->6 and 1<->2 glycosidic linkages, respectively.	3.07	5	0	raffinose family oligosaccharide; trisaccharide	mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
naringenin (S)-naringenin : The (S)-enantiomer of naringenin.	2.72	3	0	(2S)-flavan-4-one; naringenin	expectorant; plant metabolite
diaminopimelic acid Diaminopimelic Acid: A diamino derivative of heptanedioic acid with amino groups at C-2 and C-6 and the general formula (COOH)CH(NH2)CH2CH2CH2CH(NH2)(COOH).. LL-2,6-diaminopimelic acid : A 2,6-diaminopimelic acid in which both chiral centres have S configuration. It is a component of bacterial cell wall.	2.41	2	0	2,6-diaminopimelic acid; amino acid zwitterion	Escherichia coli metabolite
dithioerythritol [no description available]	1.97	1	0	1,4-dimercaptobutane-2,3-diol	reducing agent
inositol 1,4,5-trisphosphate Inositol 1,4,5-Trisphosphate: Intracellular messenger formed by the action of phospholipase C on phosphatidylinositol 4,5-bisphosphate, which is one of the phospholipids that make up the cell membrane. Inositol 1,4,5-trisphosphate is released into the cytoplasm where it releases calcium ions from internal stores within the cell's endoplasmic reticulum. These calcium ions stimulate the activity of B kinase or calmodulin.	1.97	1	0	myo-inositol trisphosphate	mouse metabolite
ouabain Ouabain: A cardioactive glycoside consisting of rhamnose and ouabagenin, obtained from the seeds of Strophanthus gratus and other plants of the Apocynaceae; used like DIGITALIS. It is commonly used in cell biological studies as an inhibitor of the NA(+)-K(+)-EXCHANGING ATPASE.. cardiac glycoside : Steroid lactones containing sugar residues that act on the contractile force of the cardiac muscles.. ouabain : A steroid hormone that is a multi-hydroxylated alpha-L-rhamnosyl cardenoloide. It binds to and inhibits the plasma membrane Na(+)/K(+)-ATPase (sodium pump). It has been isolated naturally from Strophanthus gratus.	6.42	56	0	11alpha-hydroxy steroid; 14beta-hydroxy steroid; 5beta-hydroxy steroid; alpha-L-rhamnoside; cardenolide glycoside; steroid hormone	anti-arrhythmia drug; cardiotonic drug; EC 2.3.3.1 [citrate (Si)-synthase] inhibitor; EC 3.1.3.41 (4-nitrophenylphosphatase) inhibitor; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; ion transport inhibitor; plant metabolite
taxifolin (+)-taxifolin : A taxifolin that has (2R,3R)-configuration.	2.04	1	0	taxifolin	metabolite
desmosterol Desmosterol: An intermediate in the synthesis of cholesterol.. desmosterol : A cholestanoid that is cholesta-5,24-diene substituted by a beta-hydroxy group at position 3. It is an intermediate metabolite obtained during the synthesis of cholesterol.	1.94	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; C27-steroid; cholestanoid	human metabolite; mouse metabolite
taurolithocholic acid Taurolithocholic Acid: A bile salt formed in the liver from lithocholic acid conjugation with taurine, usually as the sodium salt. It solubilizes fats for absorption and is itself absorbed. It is a cholagogue and choleretic.. taurolithocholic acid : The bile acid taurine conjugate of lithocholic acid.	4.99	39	0	bile acid taurine conjugate; monocarboxylic acid amide	human metabolite
nitroarginine Nitroarginine: An inhibitor of nitric oxide synthetase which has been shown to prevent glutamate toxicity. Nitroarginine has been experimentally tested for its ability to prevent ammonia toxicity and ammonia-induced alterations in brain energy and ammonia metabolites. (Neurochem Res 1995:200(4):451-6). N(gamma)-nitro-L-arginine : An L-arginine derivative that is L-arginine in which the terminal nitrogen of the guanidyl group is replaced by a nitro group.	2	1	0	guanidines; L-arginine derivative; N-nitro compound; non-proteinogenic L-alpha-amino acid
adenosine 5'-o-(3-thiotriphosphate) adenosine 5'-O-(3-thiotriphosphate): RN given refers to cpd with unspecified locant for thio group; see also records for 1-thio & 2-thio-isomers. adenosine 5'-[gamma-thio]triphosphate : A nucleoside triphosphate analogue that is ATP in which one of the oxygens attached to 3-phosphate group is replaced by sulfur.	1.98	1	0	nucleoside triphosphate analogue
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.	2	1	0	dehydroascorbic acid; vitamin C	coenzyme; mouse metabolite
estradiol-3-glucuronide estradiol-3-glucuronide: RN given refers to (beta-D)-glucopyranosiduronic acid (17beta)-isomer. 17beta-estradiol 3-glucosiduronic acid : A steroid glucosiduronic acid that consists of 17beta-estradiol having a beta-glucuronyl residue attached at position 3 via a glycosidic linkage.	3.37	7	0	17beta-hydroxy steroid; beta-D-glucosiduronic acid; steroid glucosiduronic acid	human metabolite; mouse metabolite
arbutin hydroquinone O-beta-D-glucopyranoside : A monosaccharide derivative that is hydroquinone attached to a beta-D-glucopyranosyl residue at position 4 via a glycosidic linkage.	1.95	1	0	beta-D-glucoside; monosaccharide derivative	Escherichia coli metabolite; plant metabolite
quinidine Quinidine: An optical isomer of quinine, extracted from the bark of the CHINCHONA tree and similar plant species. This alkaloid dampens the excitability of cardiac and skeletal muscles by blocking sodium and potassium currents across cellular membranes. It prolongs cellular ACTION POTENTIALS, and decreases automaticity. Quinidine also blocks muscarinic and alpha-adrenergic neurotransmission.. quinidine : A cinchona alkaloid consisting of cinchonine with the hydrogen at the 6-position of the quinoline ring substituted by methoxy.	4.81	10	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
meropenem Meropenem: A thienamycin derivative antibacterial agent that is more stable to renal dehydropeptidase I than IMIPENEM, but does not need to be given with an enzyme inhibitor such as CILASTATIN. It is used in the treatment of bacterial infections, including infections in immunocompromised patients.. meropenem : A carbapenemcarboxylic acid in which the azetidine and pyrroline rings carry 1-hydroxymethyl and in which the azetidine and pyrroline rings carry 1-hydroxymethyl and 5-(dimethylcarbamoyl)pyrrolidin-3-ylthio substituents respectively.	2.96	4	0	alpha,beta-unsaturated monocarboxylic acid; carbapenemcarboxylic acid; organic sulfide; pyrrolidinecarboxamide	antibacterial agent; antibacterial drug; drug allergen
griseofulvin Griseofulvin: An antifungal agent used in the treatment of TINEA infections.. griseofulvin : An oxaspiro compound produced by Penicillium griseofulvum. It is used by mouth as an antifungal drug for infections involving the scalp, hair, nails and skin that do not respond to topical treatment.	3.51	8	0	1-benzofurans; antibiotic antifungal drug; benzofuran antifungal drug; organochlorine compound; oxaspiro compound	antibacterial agent; Penicillium metabolite
monensin Monensin: An antiprotozoal agent produced by Streptomyces cinnamonensis. It exerts its effect during the development of first-generation trophozoites into first-generation schizonts within the intestinal epithelial cells. It does not interfere with hosts' development of acquired immunity to the majority of coccidial species. Monensin is a sodium and proton selective ionophore and is widely used as such in biochemical studies.. monensin A : A spiroketal, monensin A is the major component of monensin, a mixture of antibiotic substances produced by Streptomyces cinnamonensis. An antiprotozoal, it is used as the sodium salt as a feed additive for the prevention of coccidiosis in poultry and as a growth promoter in cattle.	2.89	4	0	cyclic hemiketal; monocarboxylic acid; polyether antibiotic; spiroketal	antifungal agent; coccidiostat; ionophore
cefoxitin Cefoxitin: A semisynthetic cephamycin antibiotic resistant to beta-lactamase.. cefoxitin : A semisynthetic cephamycin antibiotic which, in addition to the methoxy group at the 7alpha position, has 2-thienylacetamido and carbamoyloxymethyl side-groups. It is resistant to beta-lactamase.	2.73	3	0	beta-lactam antibiotic allergen; cephalosporin; cephamycin; semisynthetic derivative	antibacterial drug
digitoxin Digitoxin: A cardiac glycoside sometimes used in place of DIGOXIN. It has a longer half-life than digoxin; toxic effects, which are similar to those of digoxin, are longer lasting. (From Martindale, The Extra Pharmacopoeia, 30th ed, p665). digitoxin : A cardenolide glycoside in which the 3beta-hydroxy group of digitoxigenin carries a 2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl trisaccharide chain.	2.86	4	0	cardenolide glycoside	EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor
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.	4.25	5	0	L-asparagine derivative; quinolines	antiviral drug; HIV protease inhibitor
pentazocine Pentazocine: The first mixed agonist-antagonist analgesic to be marketed. It is an agonist at the kappa and sigma opioid receptors and has a weak antagonist action at the mu receptor. (From AMA Drug Evaluations Annual, 1991, p97)	1.99	1	0	benzazocine
pancuronium Pancuronium: A bis-quaternary steroid that is a competitive nicotinic antagonist. As a neuromuscular blocking agent it is more potent than CURARE but has less effect on the circulatory system and on histamine release.. pancuronium : A steroid ester in which a 5alpha-androstane skeleton is C-3alpha- and C-17beta-disubstituted with acetoxy groups and 2beta- and 16beta-disubstituted with 1-methylpiperidinium-1-yl groups. It is a non-depolarizing curare-mimetic muscle relaxant.	2.66	3	0	acetate ester; steroid ester	cholinergic antagonist; muscle relaxant; nicotinic antagonist
rocuronium Rocuronium: An androstanol non-depolarizing neuromuscular blocking agent. It has a mono-quaternary structure and is a weaker nicotinic antagonist than PANCURONIUM.. rocuronium : A 5alpha-androstane compound having 3alpha-hydroxy-, 17beta-acetoxy-, 2beta-morpholino- and 16beta-N-allyllyrrolidinium substituents.	7.9	4	0	3alpha-hydroxy steroid; acetate ester; androstane; morpholines; quaternary ammonium ion; tertiary amino compound	drug allergen; muscle relaxant; neuromuscular agent
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.	2.04	1	0	17-oxo steroid; 3beta-hydroxy steroid; androstanoid	androgen; human metabolite
phalloidine Phalloidine: Very toxic polypeptide isolated mainly from AMANITA phalloides (Agaricaceae) or death cup; causes fatal liver, kidney and CNS damage in mushroom poisoning; used in the study of liver damage.. phalloidin : A homodetic bicyclic heptapeptide having a sulfide bridge.	3.59	9	0	homodetic cyclic peptide
ryanodine Ryanodine: A methylpyrrole-carboxylate from RYANIA that disrupts the RYANODINE RECEPTOR CALCIUM RELEASE CHANNEL to modify CALCIUM release from SARCOPLASMIC RETICULUM resulting in alteration of MUSCLE CONTRACTION. It was previously used in INSECTICIDES. It is used experimentally in conjunction with THAPSIGARGIN and other inhibitors of CALCIUM ATPASE uptake of calcium into SARCOPLASMIC RETICULUM.. ryanodine : An insecticide alkaloid isolated from South American plant Ryania speciosa.	2.11	1	0
ferruginol ferruginol: structure in first source. ferruginol : An abietane diterpenoid that is abieta-8,11,13-triene substituted by a hydroxy group at positions 12.	2.03	1	0	abietane diterpenoid; carbotricyclic compound; meroterpenoid; phenols	antibacterial agent; antineoplastic agent; plant metabolite; protective agent
naringin [no description available]	3.57	2	0	(2S)-flavan-4-one; 4'-hydroxyflavanones; dihydroxyflavanone; disaccharide derivative; neohesperidoside	anti-inflammatory agent; antineoplastic agent; metabolite
ochratoxin a ochratoxin A: structure in first source & in Merck, 9th ed, #6549. ochratoxin A : A phenylalanine derivative resulting from the formal condensation of the amino group of L-phenylalanine with the carboxy group of (3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carboxylic acid (ochratoxin alpha). It is among the most widely occurring food-contaminating mycotoxins, produced by Aspergillus ochraceus, Aspergillus carbonarius and Penicillium verrucosum.	3.39	7	0	isochromanes; monocarboxylic acid amide; N-acyl-L-phenylalanine; organochlorine compound; phenylalanine derivative	Aspergillus metabolite; calcium channel blocker; carcinogenic agent; mycotoxin; nephrotoxin; Penicillium metabolite; teratogenic agent
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)	1.97	1	0
estriol 3-glucuronide estriol 3-glucuronide: RN given refers to beta-D glucopyranosiduronic acid (16alpha,17beta)-isomer. estriol 3-O-(beta-D-glucuronide) : A steroid glucosiduronic acid that is the 3-beta-D-glucuronide of estriol; a steroid hormone ligand recognised by the monoclonal antibody 4155.	2.01	1	0	16alpha-hydroxy steroid; 17beta-hydroxy steroid; steroid glucosiduronic acid	epitope; estrogen
acetylleucyl-leucyl-norleucinal acetylleucyl-leucyl-norleucinal: a proteasome inhibitor. acetylleucyl-leucyl-norleucinal : A tripeptide composed of N-acetylleucyl, leucyl and norleucinal residues joined in sequence.	2.01	1	0	aldehyde; tripeptide	cysteine protease inhibitor
bq 123 cyclo(Trp-Asp-Pro-Val-Leu): derived from the modification of a natural lead of BE-18257B, an endothelin A receptor antagonist; has neuroprotective activity; amino acid sequence given in first source	3.1	5	0	cyclic peptide
e 3040 E 3040: a dual inhibitor of 5-lipoxygenase and thromboxane A2 synthetase; structure given in first source	2.4	2	0	benzothiazoles; organic hydroxy compound; pyridines; secondary amino compound	anti-inflammatory drug; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; uricosuric drug
E3040 glucuronide E3040 glucuronide : A member of the class of benzothiazoles that is E3040 in which the hydroxy hydrogen at position 6 has been replaced by a beta-D-glucosiduronic acid group. It is a metabolite of the anti-inflammatory drug, E3040.	2.01	1	0	benzothiazoles; beta-D-glucosiduronic acid; pyridines; secondary amino compound	xenobiotic metabolite
devazepide Devazepide: A derivative of benzodiazepine that acts on the cholecystokinin A (CCKA) receptor to antagonize CCK-8's (SINCALIDE) physiological and behavioral effects, such as pancreatic stimulation and inhibition of feeding.. devazepide : An indolecarboxamide obtained by formal condensation of the carboxy group of indole-2-carboxylic acid with the exocyclic amino group of (3S)-3-amino-1-methyl-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one. A cholecystokinin antagonist used for treatment of gastrointestinal disorders.	2.38	2	0	1,4-benzodiazepinone; indolecarboxamide	antineoplastic agent; apoptosis inducer; cholecystokinin antagonist; gastrointestinal drug
sodium arsenite sodium arsenite : An inoganic sodium salt with formula with formula NaAsO2.	2.89	1	0	arsenic molecular entity; inorganic sodium salt	antibacterial agent; antifungal agent; antineoplastic agent; carcinogenic agent; herbicide; insecticide; rodenticide
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	3.82	11	0	cyclodextrin
sucrose octasulfate [no description available]	1.97	1	0
acarbose [no description available]	2.07	1	0	amino cyclitol; glycoside
7-ketolithocholic acid 7-ketolithocholic acid: RN given refers to (3alpha,5beta)-isomer. 7-oxolithocholic acid : A bile acid that is lithocholic acid carrying an additional oxo substituent at position 7.	2.67	3	0	3alpha-hydroxy steroid; bile acid; monohydroxy-5beta-cholanic acid; oxo-5beta-cholanic acid	human metabolite
acetyl coenzyme a Acetyl Coenzyme A: Acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent.	2.15	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	2.03	1	0	cinnamic acid	plant metabolite
ergosterol [no description available]	2.41	2	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; ergostanoid; phytosterols	fungal metabolite; Saccharomyces cerevisiae metabolite
trichostatin a trichostatin A: chelates zinc ion in the active site of histone deacetylases, resulting in preventing histone unpacking so DNA is less available for transcription; do not confuse with TRICHOSANTHIN which is a protein; found in STREPTOMYCES	2.11	1	0	antibiotic antifungal agent; hydroxamic acid; trichostatin	bacterial metabolite; EC 3.5.1.98 (histone deacetylase) inhibitor; geroprotector
tretinoin Tretinoin: An important regulator of GENE EXPRESSION during growth and development, and in NEOPLASMS. Tretinoin, also known as retinoic acid and derived from maternal VITAMIN A, is essential for normal GROWTH; and EMBRYONIC DEVELOPMENT. An excess of tretinoin can be teratogenic. It is used in the treatment of PSORIASIS; ACNE VULGARIS; and several other SKIN DISEASES. It has also been approved for use in promyelocytic leukemia (LEUKEMIA, PROMYELOCYTIC, ACUTE).. retinoic acid : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraenoic acid substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).. all-trans-retinoic acid : A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry.	1.96	1	0	retinoic acid; vitamin A	anti-inflammatory agent; antineoplastic agent; antioxidant; AP-1 antagonist; human metabolite; keratolytic drug; retinoic acid receptor agonist; retinoid X receptor agonist; signalling molecule
arachidonic acid icosa-5,8,11,14-tetraenoic acid : Any icosatetraenoic acid with the double bonds at positions 5, 8, 11 and 14.. arachidonate : A long-chain fatty acid anion resulting from the removal of a proton from the carboxy group of arachidonic acid.	2.88	4	0	icosa-5,8,11,14-tetraenoic acid; long-chain fatty acid; omega-6 fatty acid	Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite; mouse metabolite
alpha-cyclodextrin alpha-cyclodextrin : A cycloamylose composed of six alpha-(1->4) linked D-glucopyranose units.	2.06	1	0	cyclodextrin
3-hydroxy-3-methylglutaryl-coenzyme a 3-hydroxy-3-methylglutaryl-coenzyme A: RN given refers to cpd without isomeric designation. 3-hydroxy-3-methylglutaryl-CoA : An alpha,omega dicarboxyacyl-CoA that results from the formal condensation of the thiol group of coenzyme A with one of the carboxy groups of 3-hydroxy-3-methylglutaric acid.. (3S)-3-hydroxy-3-methylglutaryl-CoA : A 3-hydroxy-3-methylglutaryl-CoA where the 3-hydroxy-3-methylglutaryl component has (S)-configuration.	2.39	2	0	3-hydroxy-3-methylglutaryl-CoA; 3-hydroxy fatty acyl-CoA	human metabolite; mouse metabolite
resveratrol trans-resveratrol : A resveratrol in which the double bond has E configuration.	3.56	8	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).	3.99	14	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.	5.03	41	0	octadec-9-enoic acid	antioxidant; Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; Escherichia coli metabolite; mouse metabolite; plant metabolite; solvent
tacrolimus Tacrolimus: A macrolide isolated from the culture broth of a strain of Streptomyces tsukubaensis that has strong immunosuppressive activity in vivo and prevents the activation of T-lymphocytes in response to antigenic or mitogenic stimulation in vitro.. tacrolimus (anhydrous) : A macrolide lactam containing a 23-membered lactone ring, originally isolated from the fermentation broth of a Japanese soil sample that contained the bacteria Streptomyces tsukubaensis.	2.7	3	0	macrolide lactam	bacterial metabolite; immunosuppressive agent
pectins Pectins: High molecular weight polysaccharides present in the cell walls of all plants. Pectins cement cell walls together. They are used as emulsifiers and stabilizers in the food industry. They have been tried for a variety of therapeutic uses including as antidiarrheals, where they are now generally considered ineffective, and in the treatment of hypercholesterolemia.. alpha-D-galacturonic acid : The alpha-anomer of D-galacturonic acid.	4.6	6	1	D-galactopyranuronic acid
cerivastatin cerivastatin: cerivastatin is the ((E)-(+))-isomer; structure given in first source. cerivastatin : (3R,5S)-3,5-dihydroxyhept-6-enoic acid in which the (7E)-hydrogen is substituted by a 4-(4-fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)pyridin-3-yl group. Formerly used (as its sodium salt) to lower cholesterol and prevent cardiovascular disease, it was withdrawn from the market worldwide in 2001 following reports of a severe form of muscle toxicity.	2.07	1	0	dihydroxy monocarboxylic acid; pyridines; statin (synthetic)
rosuvastatin rosuvastatin : A dihydroxy monocarboxylic acid that is (6E)-7-{4-(4-fluorophenyl)-2-[methyl(methylsulfonyl)amino]-6-(propan-2-yl)pyrimidin-5-yl} hept-6-enoic acid carrying two hydroxy substituents at positions 3 and 5 (the 3R,5S-diastereomer).	2.07	1	0	dihydroxy monocarboxylic acid; monofluorobenzenes; pyrimidines; statin (synthetic); sulfonamide	anti-inflammatory agent; antilipemic drug; cardioprotective agent; CETP inhibitor; environmental contaminant; xenobiotic
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.	2.4	2	0	butyrate ester; organic heterotricyclic compound; sesquiterpene lactone	calcium channel blocker; EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor
clindamycin Clindamycin: An antibacterial agent that is a semisynthetic analog of LINCOMYCIN.. clindamycin : A carbohydrate-containing antibiotic that is the semisynthetic derivative of lincomycin, a natural antibiotic.	1.99	1	0
lycopene [no description available]	2.11	1	0	acyclic carotene	antioxidant; plant metabolite
zithromax Azithromycin: A semi-synthetic macrolide antibiotic structurally related to ERYTHROMYCIN. It has been used in the treatment of Mycobacterium avium intracellulare infections, toxoplasmosis, and cryptosporidiosis.. azithromycin : A macrolide antibiotic useful for the treatment of bacterial infections.	2.75	3	0	macrolide antibiotic	antibacterial drug; environmental contaminant; xenobiotic
obeticholic acid obeticholic acid: A farnesoid X receptor agonist and anticholestatic agent that is used in the treatment of chronic liver diseases; structure in first source.. obeticholic acid : A dihydroxy-5beta-cholanic acid that is chenodeoxycholic acid carrying an additional ethyl substituent at the 6alpha-position. A semi-synthetic bile acid which acts as a farnesoid X receptor agonist and is used for treatment of primary biliary cholangitis.	3.99	3	0	3alpha-hydroxy steroid; 7alpha-hydroxy steroid; dihydroxy-5beta-cholanic acid	farnesoid X receptor agonist; hepatoprotective agent
y 27632 Y 27632: RN given for di-HCl salt; inhibits Rho-associated protein kinase; inhibits calcium sensitization to affect smooth muscle relaxation; structure in first source. Y-27632 : A monocarboxylic acid amide that is trans-[(1R)-1-aminoethyl]cyclohexanecarboxamide in which one of the nitrogens of the aminocarbony group is substituted by a pyridine nucleus. It has been shown to exhibit inhibitory activity against Rho-associated protein kinase (ROCK) enzyme.	2.49	2	0	aromatic amide
prostaglandin d2 Prostaglandin D2: The principal cyclooxygenase metabolite of arachidonic acid. It is released upon activation of mast cells and is also synthesized by alveolar macrophages. Among its many biological actions, the most important are its bronchoconstrictor, platelet-activating-factor-inhibitory, and cytotoxic effects.. prostaglandin D2 : A member of the class of prostaglandins D that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9 and 15 and an oxo group at position 11 (the 5Z,9alpha,13E,15S- stereoisomer).	3.09	5	0	prostaglandins D	human metabolite; mouse metabolite
diethylstilbestrol Diethylstilbestrol: A synthetic nonsteroidal estrogen used in the treatment of menopausal and postmenopausal disorders. It was also used formerly as a growth promoter in animals. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), diethylstilbestrol has been listed as a known carcinogen. (Merck, 11th ed). diethylstilbestrol : An olefinic compound that is trans-hex-3-ene in which the hydrogens at positions 3 and 4 have been replaced by p-hydroxyphenyl groups.	2.9	4	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
sulfolithocholic acid sulfolithocholic acid: RN refers to (3alpha,5beta)-isomer. lithocholic acid sulfate : A steroid sulfate that is lithocholic acid in which the hydroxy hydrogen at position 3 has been replaced by a sulfo group.	3.1	5	0	steroid sulfate
texas red Texas red: hydrophilic Texas red; structure given in first source	2.04	1	0	organic heteroheptacyclic compound	fluorochrome
laminaran laminaran: beta-1,3-glucan	2.31	1	0
cefamandole Cefamandole: Semisynthetic wide-spectrum cephalosporin with prolonged action, probably due to beta-lactamase resistance. It is used also as the nafate.. cefamandole : A cephalosporin compound having (R)-mandelamido and N-methylthiotetrazole side-groups.	3.62	3	0	cephalosporin; semisynthetic derivative	antibacterial drug
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)	2.37	2	0	actinomycin	mutagen
gamma-sitosterol clionasterol : A member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3.	3.38	7	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; phytosterols	marine metabolite; plant metabolite
melphalan Melphalan: An alkylating nitrogen mustard that is used as an antineoplastic in the form of the levo isomer - MELPHALAN, the racemic mixture - MERPHALAN, and the dextro isomer - MEDPHALAN; toxic to bone marrow, but little vesicant action; potential carcinogen.. melphalan : A phenylalanine derivative comprising L-phenylalanine having [bis(2-chloroethyl)amino group at the 4-position on the phenyl ring.	1.95	1	0	L-phenylalanine derivative; nitrogen mustard; non-proteinogenic L-alpha-amino acid; organochlorine compound	alkylating agent; antineoplastic agent; carcinogenic agent; drug allergen; immunosuppressive agent
enkephalin, leucine Enkephalin, Leucine: One of the endogenous pentapeptides with morphine-like activity. It differs from MET-ENKEPHALIN in the LEUCINE at position 5. Its first four amino acid sequence is identical to the tetrapeptide sequence at the N-terminal of BETA-ENDORPHIN.. Leu-enkephalin : A pentapeptide comprising L-tyrosine, glycine, glycine, L-phenylalanine and L-leucine residues joined in sequence by peptide linkages. It is an endogenous opioid peptide produced in vertebrate species, including rodents, primates and humans that results from decomposition of proenkephalin or dynorphin and exhibits antinociceptive properties.	2.01	1	0	pentapeptide; peptide zwitterion	analgesic; delta-opioid receptor agonist; human metabolite; mu-opioid receptor agonist; neurotransmitter; rat metabolite
benzyloxycarbonylleucyl-leucyl-leucine aldehyde benzyloxycarbonylleucyl-leucyl-leucine aldehyde: proteasome inhibitor. N-benzyloxycarbonyl-L-leucyl-L-leucyl-L-leucinal : A tripeptide that is L-leucyl-L-leucyl-L-leucine in which the C-terminal carboxy group has been reduced to the corresponding aldehyde and the N-terminal amino group is protected as its benzyloxycarbonyl derivative.	2.44	2	0	amino aldehyde; carbamate ester; tripeptide	proteasome inhibitor
tenofovir tenofovir (anhydrous) : A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens is replaced by a [(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(isopropyloxycarbonyloxymethyl) ester (disoproxil ester) prodrug is used as the fumaric acid salt in combination therapy for the treatment of HIV infection.	3.82	3	0	nucleoside analogue; phosphonic acids	antiviral drug; drug metabolite; HIV-1 reverse transcriptase inhibitor
riboflavin vitamin B2 : Any member of a group of vitamers that belong to the chemical structural class called flavins that exhibit biological activity against vitamin B2 deficiency. Symptoms associated with vitamin B2 deficiency include glossitis, seborrhea, angular stomaitis, cheilosis and photophobia. The vitamers include riboflavin and its phosphate derivatives (and includes their salt, ionised and hydrate forms).	2.44	2	0	flavin; vitamin B2	anti-inflammatory agent; antioxidant; cofactor; Escherichia coli metabolite; food colouring; fundamental metabolite; human urinary metabolite; mouse metabolite; photosensitizing agent; plant metabolite
sodium bicarbonate Sodium Bicarbonate: A white, crystalline powder that is commonly used as a pH buffering agent, an electrolyte replenisher, systemic alkalizer and in topical cleansing solutions.	2.66	3	0	one-carbon compound; organic sodium salt	antacid; food anticaking agent
cholestane-3,5,6-triol cholestane-3,5,6-triol: structure; RN given refers to cpd without isomeric designation	2	1	0
carbenoxolone sodium Carbenoxolone: An agent derived from licorice root. It is used for the treatment of digestive tract ulcers, especially in the stomach. Antidiuretic side effects are frequent, but otherwise the drug is low in toxicity.	1.96	1	0	triterpenoid
cefpiramide cefpiramide: antipseudomonal cephalosporin derivative. cefpiramide : A third-generation cephalosporin antibiotic with [(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl and (R)-2-{[(4-hydroxy-6-methylpyridin-3-yl)carbonyl]amino}-2-(4-hydroxyphenyl)acetamido groups at positions 3 and 7, respectively, of the cephem skeleton. It has a broad spectrum of antibacterial activity.	2.39	2	0	carboxylic acid; cephalosporin	antibacterial drug
glycosides [no description available]	3.22	6	0
chalcone trans-chalcone : The trans-isomer of chalcone.	3.07	5	0	chalcone	EC 3.2.1.1 (alpha-amylase) inhibitor
isomethyleugenol Methylation: Addition of methyl groups. In histo-chemistry methylation is used to esterify carboxyl groups and remove sulfate groups by treating tissue sections with hot methanol in the presence of hydrochloric acid. (From Stedman, 25th ed)	3.09	5	0	isomethyleugenol
squalene Addavax: an oil-water nanoemulsion and adjuvant containing squalene, Tween 80, and sorbitane trioleate	2	1	0	triterpene	human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	3.42	7	0	stilbene
ricinoleic acid ricinoleic acid: RN given refers to (R-(Z))-isomer; structure in Merck Index, 9th ed, #8005. ricinoleic acid : A (9Z)-12-hydroxyoctadec-9-enoic acid in which the 12-hydroxy group has R-configuration..	1.96	1	0	(9Z)-12-hydroxyoctadec-9-enoic acid
buprenorphine Buprenorphine: A derivative of the opioid alkaloid THEBAINE that is a more potent and longer lasting analgesic than MORPHINE. It appears to act as a partial agonist at mu and kappa opioid receptors and as an antagonist at delta receptors. The lack of delta-agonist activity has been suggested to account for the observation that buprenorphine tolerance may not develop with chronic use.. buprenorphine : A morphinane alkaloid that is 7,8-dihydromorphine 6-O-methyl ether in which positions 6 and 14 are joined by a -CH2CH2- bridge, one of the hydrogens of the N-methyl group is substituted by cyclopropyl, and a hydrogen at position 7 is substituted by a 2-hydroxy-3,3-dimethylbutan-2-yl group. It is highly effective for the treatment of opioid use disorder and is also increasingly being used in the treatment of chronic pain.	1.97	1	0	morphinane alkaloid	delta-opioid receptor antagonist; kappa-opioid receptor antagonist; mu-opioid receptor agonist; opioid analgesic
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.	3.37	7	0	vasopressin	cardiovascular drug; hematologic agent; mitogen
pyrophosphate Diphosphates: Inorganic salts of phosphoric acid that contain two phosphate groups.	1.95	1	0	diphosphate ion
triiodothyronine, reverse [no description available]	2.7	3	0	3,3',5'-triiodothyronine; amino acid zwitterion
azidopine azidopine: structure given in first source	2	1	0	benzamides
mezlocillin Mezlocillin: Semisynthetic ampicillin-derived acylureido penicillin. It has been proposed for infections with certain anaerobes and may be useful in inner ear, bile, and CNS infections.. mezlocillin : A penicillin in which the substituent at position 6 of the penam ring is a (2R)-2-[3-(methanesulfonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido group.	1.96	1	0	penicillin allergen; penicillin	antibacterial drug
polidocanol Polidocanol: An alkyl polyglycol ether of LAURYL ALCOHOL, chemically defined as an alcohol ethoxylate having an average alkyl chain of 12–14 carbon atoms, and an ethylene oxide chain of 9 ethylene oxide units. It is used as a detergent, and medically as a local anesthetic, and as a sclerosing agent for the treatment of ESOPHAGEAL AND GASTRIC VARICES and VARICOSE VEINS.. polidocanol : A hydroxypolyether that is nonaethylene glycol in which one of the terminal hydroxy functions is substituted by a lauryl (dodecyl) group.	1.98	1	0	hydroxypolyether	hepatotoxic agent; nonionic surfactant; sclerotherapy agent
iothalamate meglumine Iothalamate Meglumine: A radiopaque medium used for urography, angiography, venography, and myelography. It is highly viscous and binds to plasma proteins.	2.03	1	0	amidobenzoic acid
dithizone Dithizone: Chelating agent used for heavy metal poisoning and assay. It causes diabetes.	2.21	1	0
propylthiouracil Propylthiouracil: A thiourea antithyroid agent. Propythiouracil inhibits the synthesis of thyroxine and inhibits the peripheral conversion of throxine to tri-iodothyronine. It is used in the treatment of hyperthyroidism. (From Martindale, The Extra Pharmacopeoia, 30th ed, p534). 6-propyl-2-thiouracil : A pyrimidinethione consisting of uracil in which the 2-oxo group is substituted by a thio group and the hydrogen at position 6 is substituted by a propyl group.	2.06	1	0	pyrimidinethione	antidote to paracetamol poisoning; antimetabolite; antioxidant; antithyroid drug; carcinogenic agent; EC 1.14.13.39 (nitric oxide synthase) inhibitor; hormone antagonist
sesquiterpenes [no description available]	2.42	2	0
chlorprothixene Chlorprothixene: A thioxanthine with effects similar to the phenothiazine antipsychotics.. (Z)-chlorprothixene : A chlorprothixene in which the double bond adopts a (Z)-configuration.	2.46	2	0	chlorprothixene
cotinine Cotinine: The N-glucuronide conjugate of cotinine is a major urinary metabolite of NICOTINE. It thus serves as a biomarker of exposure to tobacco SMOKING. It has CNS stimulating properties.. (-)-cotinine : An N-alkylpyrrolidine that consists of N-methylpyrrolidinone bearing a pyridin-3-yl substituent at position C-5 (the 5S-enantiomer). It is an alkaloid commonly found in Nicotiana tabacum.	2.08	1	0	N-alkylpyrrolidine; pyridines; pyrrolidin-2-ones; pyrrolidine alkaloid	antidepressant; biomarker; human xenobiotic metabolite; plant metabolite
curcumin Curcumin: A yellow-orange dye obtained from tumeric, the powdered root of CURCUMA longa. It is used in the preparation of curcuma paper and the detection of boron. Curcumin appears to possess a spectrum of pharmacological properties, due primarily to its inhibitory effects on metabolic enzymes.. curcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa.	9.29	5	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).	2.07	1	0	carbobicyclic compound; enone; sesquiterpenoid	fragrance; insect repellent; plant metabolite
sulindac Sulindac: A sulfinylindene derivative prodrug whose sulfinyl moiety is converted in vivo to an active NSAID analgesic. Specifically, the prodrug is converted by liver enzymes to a sulfide which is excreted in the bile and then reabsorbed from the intestine. This helps to maintain constant blood levels with reduced gastrointestinal side effects.. sulindac : A monocarboxylic acid that is 1-benzylidene-1H-indene which is substituted at positions 2, 3, and 5 by methyl, carboxymethyl, and fluorine respectively, and in which the phenyl group of the benzylidene moiety is substituted at the para position by a methylsulfinyl group. It is a prodrug for the corresponding sulfide, a non-steroidal anti-inflammatory drug, used particularly in the treatment of acute and chronic inflammatory conditions.	3.14	5	0	monocarboxylic acid; organofluorine compound; sulfoxide	analgesic; antineoplastic agent; antipyretic; apoptosis inducer; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; prodrug; tocolytic agent
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.	8.95	13	0	capsaicinoid	non-narcotic analgesic; TRPV1 agonist; voltage-gated sodium channel blocker
metiamide Metiamide: A histamine H2 receptor antagonist that is used as an anti-ulcer agent.	3.56	9	0	imidazoles
terbinafine [no description available]	2.72	2	0	acetylenic compound; allylamine antifungal drug; enyne; naphthalenes; tertiary amine	EC 1.14.13.132 (squalene monooxygenase) inhibitor; P450 inhibitor; sterol biosynthesis inhibitor
tosylarginine methyl ester Tosylarginine Methyl Ester: Arginine derivative which is a substrate for many proteolytic enzymes. As a substrate for the esterase from the first component of complement, it inhibits the action of C(l) on C(4).	1.95	1	0	guanidines; L-arginine ester; methyl ester; sulfonamide
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.	7.77	3	0	cinnamate ester; tannin	food component; plant metabolite
benzotript benzotript: anti-gastrinic; active group is amide; structure	1.97	1	0
thioguanine anhydrous Thioguanine: An antineoplastic compound which also has antimetabolite action. The drug is used in the therapy of acute leukemia.. tioguanine : A 2-aminopurine that is the 6-thiono derivative of 2-amino-1,9-dihydro-6H-purine. Incorporates into DNA and inhibits synthesis. Used in the treatment of leukaemia.	2.02	1	0	2-aminopurines	anticoronaviral agent; antimetabolite; antineoplastic agent
mucochloric acid [no description available]	1.98	1	0
thiourea Thiourea: A photographic fixative used also in the manufacture of resins. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), this substance may reasonably be anticipated to be a carcinogen (Merck Index, 9th ed). Many of its derivatives are ANTITHYROID AGENTS and/or FREE RADICAL SCAVENGERS.. thiourea : The simplest member of the thiourea class, consisting of urea with the oxygen atom substituted by sulfur.	3.05	5	0	one-carbon compound; thioureas; ureas	antioxidant; chromophore
D-fructopyranose [no description available]	3.15	5	0	cyclic hemiketal; D-fructose; fructopyranose	sweetening agent
thioacetamide Thioacetamide: A crystalline compound used as a laboratory reagent in place of HYDROGEN SULFIDE. It is a potent hepatocarcinogen.. thioacetamide : A thiocarboxamide consiting of acetamide having the oxygen replaced by sulfur.	2.39	2	0	thiocarboxamide	hepatotoxic agent
brij-58 Cetomacrogol: Non-ionic surfactant of the polyethylene glycol family. It is used as a solubilizer and emulsifying agent in foods, cosmetics, and pharmaceuticals, often as an ointment base, and also as a research tool.	2.01	1	0
digoxin Digoxin: A cardiotonic glycoside obtained mainly from Digitalis lanata; it consists of three sugars and the aglycone DIGOXIGENIN. Digoxin has positive inotropic and negative chronotropic activity. It is used to control ventricular rate in ATRIAL FIBRILLATION and in the management of congestive heart failure with atrial fibrillation. Its use in congestive heart failure and sinus rhythm is less certain. The margin between toxic and therapeutic doses is small. (From Martindale, The Extra Pharmacopoeia, 30th ed, p666). digoxin : A cardenolide glycoside that is digitoxin beta-hydroxylated at C-12. A cardiac glycoside extracted from the foxglove plant, Digitalis lanata, it is used to control ventricular rate in atrial fibrillation and in the management of congestive heart failure with atrial fibrillation, but the margin between toxic and therapeutic doses is small.	5.88	31	0	cardenolide glycoside; steroid saponin	anti-arrhythmia drug; cardiotonic drug; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; epitope
capsazepine capsazepine: modified capsaicin molecule; a capsaicin receptor antagonist. capsazepine : A benzazepine that is 2,3,4,5-tetrahydro-1H-2-benzazepine which is substituted by hydroxy groups at positions 7 and 8 and on the nitrogen atom by a 2-(p-chlorophenyl)ethylaminothiocarbonyl group. A synthetic analogue of capsaicin, it was the first reported capsaicin receptor antagonist.	2.01	1	0	benzazepine; catechols; monochlorobenzenes; thioureas	capsaicin receptor antagonist
fumonisin b1 fumonisin B1: isolated from Fusarium moniliforme MRC 826; structure given in first source; has cancer-promoting activity; inhibits ceramide synthase. fumonisin B1 : A diester that results from the condensation of the 1-carboxy groups of two molecules of propane-1,2,3-tricarboxylic acid with hydroxy groups at positions 14 and 15 of (2S,3S,5R,10R,12S,14S,15R,16R)-2-amino-12,16-dimethylicosane-3,5,10,14,15-pentol.	2.01	1	0	diester; fumonisin; primary amino compound; triol	carcinogenic agent; metabolite
tamoxifen [no description available]	2.95	4	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
sodium taurodeoxycholate Taurodeoxycholic Acid: A bile salt formed in the liver by conjugation of deoxycholate with taurine, usually as the sodium salt. It is used as a cholagogue and choleretic, also industrially as a fat emulsifier.. taurodeoxycholic acid : A bile acid taurine conjugate of deoxycholic acid.. taurodeoxycholate : An organosulfonate oxoanion that is the conjugate base of taurodeoxycholic acid.	7.44	116	1	bile acid taurine conjugate	human metabolite
4-methylumbelliferyl glucoside 4-methylumbelliferyl glucoside: RN given refers to (beta)-isomer. 4-methylumbelliferyl beta-D-glucoside : A beta-D-glucoside having a 4-methylumbelliferyl substituent at the anomeric position.	2.37	2	0	beta-D-glucoside; coumarins; monosaccharide derivative	chromogenic compound
indoxyl glucuronide indoxyl glucuronide: substrate for the detection of E coli in urine	2.02	1	0	glucosiduronic acid
nadp [no description available]	4.16	5	0
1,1-diphenyl-2-picrylhydrazyl 1,1-diphenyl-2-picrylhydrazyl: A diphenyl picrate; the ability to decolorize this stable radical indicates reactivity of tested compounds (Banda, Anal Chem 46:1772-7 1974)	2.44	2	0
nap taurine NAP taurine: photochemical labelling reagent for erythrocyte membrane; structure	1.96	1	0
fusidic acid Fusidic Acid: An antibiotic isolated from the fermentation broth of Fusidium coccineum. (From Merck Index, 11th ed). It acts by inhibiting translocation during protein synthesis.. fusidic acid : A steroid antibiotic that is isolated from the fermentation broth of Fusidium coccineum.	3.68	10	0	11alpha-hydroxy steroid; 3alpha-hydroxy steroid; alpha,beta-unsaturated monocarboxylic acid; steroid acid; steroid antibiotic; sterol ester	EC 2.7.1.33 (pantothenate kinase) inhibitor; Escherichia coli metabolite; protein synthesis inhibitor
lincomycin Lincomycin: An antibiotic produced by Streptomyces lincolnensis var. lincolnensis. It has been used in the treatment of staphylococcal, streptococcal, and Bacteroides fragilis infections.. lincomycin : A carbohydrate-containing antibiotic produced by the actinomyces Streptomyces lincolnensis.	2.38	2	0	carbohydrate-containing antibiotic; L-proline derivative; monocarboxylic acid amide; pyrrolidinecarboxamide; S-glycosyl compound	antimicrobial agent; bacterial metabolite
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.	3.08	5	0	cyclodepsipeptide; macrocycle	antimicrobial agent; antiviral agent; bacterial metabolite; potassium ionophore
estrone sulfate estrone sulfate: sulfoconjugated estrone; RN given refers to parent cpd	6.92	53	0	17-oxo steroid; steroid sulfate	human metabolite; mouse metabolite
ranitidine Ranitidine: A non-imidazole blocker of those histamine receptors that mediate gastric secretion (H2 receptors). It is used to treat gastrointestinal ulcers.. ranitidine : A member of the class of furans used to treat peptic ulcer disease (PUD) and gastroesophageal reflux disease.	4.46	5	1	C-nitro compound; furans; organic sulfide; tertiary amino compound	anti-ulcer drug; drug allergen; environmental contaminant; H2-receptor antagonist; xenobiotic
u 0126 U 0126: protein kinase kinase inhibitor; structure in first source	2.17	1	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
glycylproline Gly-Pro : A dipeptide consisting of L-proline having a glycyl residue attached to its alpha-amino group.	3.57	2	0	dipeptide zwitterion; dipeptide	metabolite
n-bromotaurine N-bromotaurine: cpd able to kill the schistosomula of Schistosoma mansoni	2.02	1	0
lithium Lithium: An element in the alkali metals family. It has the atomic symbol Li, atomic number 3, and atomic weight [6.938; 6.997]. Salts of lithium are used in treating BIPOLAR DISORDER.	3.66	10	0	alkali metal atom
raclopride Raclopride: A substituted benzamide that has antipsychotic properties. It is a dopamine D2 receptor (see RECEPTORS, DOPAMINE D2) antagonist.	2.06	1	0	salicylamides
orlistat Orlistat: A lactone derivative of LEUCINE that acts as a pancreatic lipase inhibitor to limit the absorption of dietary fat; it is used in the management of obesity.. orlistat : A carboxylic ester resulting from the formal condensation of the carboxy group of N-formyl-L-leucine with the hydroxy group of (3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one. A pancreatic lipase inhibitor, it is used as an anti-obesity drug.	2.68	3	0	beta-lactone; carboxylic ester; formamides; L-leucine derivative	anti-obesity agent; bacterial metabolite; EC 2.3.1.85 (fatty acid synthase) inhibitor; EC 3.1.1.3 (triacylglycerol lipase) inhibitor
quinine [no description available]	4.48	7	0	cinchona alkaloid	antimalarial; muscle relaxant; non-narcotic analgesic
tauro-24,25-dihydrofusidate tauro-24,25-dihydrofusidate: affects nasal absorption of insulin in sheep	1.98	1	0
boc-tyr(s03)-nle-gly-trp-nle-asp-2-phenylethyl ester JMV 180: distinguishes high-affinity cholecystokinin receptors from low-affinity cholecystokinin receptors; RN given refers to (S)-isomer	2.02	1	0
glycodeoxycholic acid Glycodeoxycholic Acid: A bile salt formed in the liver by conjugation of deoxycholate with glycine, usually as the sodium salt. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and choleretic.. glycodeoxycholic acid : A bile acid glycine conjugate of deoxycholic acid.	4.73	30	0	bile acid glycine conjugate	human metabolite
asperlicin asperlicin: cholecystokinin antagonist; isolated from Aspergillus alliaceus; structure given in first source	1.97	1	0
fk 838 FK 838: an adenosine subtype-1 receptor antagonist; structure given in first source	2	1	0
glutathione glycylethyl ester [no description available]	2	1	0
cystine [no description available]	7.65	3	0
12-ketolithocholic acid 12-ketolithocholic acid: RN given refers to (3alpha,5beta)-isomer	2.05	1	0	bile acid
carbonyl 3-chlorophenylhydrazone carbonyl 3-chlorophenylhydrazone: inhibitor of ATP synthesis; inhibits iron-containing nitrile hydratases	2.06	1	0
zd 6474 CH 331: structure in first source	2.25	1	0	aromatic ether; organobromine compound; organofluorine compound; piperidines; quinazolines; secondary amine	antineoplastic agent; tyrosine kinase inhibitor
chenodeoxycholate sulfate conjugate chenodeoxycholate sulfate conjugate: ester not salt of chenodeoxycholic acid; major product of enzymatic sulfation of chenodeoxycholic acid	1.96	1	0
amanitins Amanitins: Cyclic peptides extracted from carpophores of various mushroom species. They are potent inhibitors of RNA polymerases in most eukaryotic species, blocking the production of mRNA and protein synthesis. These peptides are important in the study of transcription. Alpha-amanitin is the main toxin from the species Amanitia phalloides, poisonous if ingested by humans or animals.	2.38	2	0
cytellin cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982	3.98	14	0
2-(4-(2-carboxyethyl)phenethylamino)-5'-n-ethylcarboxamidoadenosine 2-(4-(2-carboxyethyl)phenethylamino)-5'-N-ethylcarboxamidoadenosine: A2 adenosine receptor agonist; structure given in first source. CGS-21680 : A derivative of adenosine in which the 5'-hydroxymethyl group is replaced by N-ethylcarboxamido and the hydrogen at position 2 on the adenine is replaced by a 4-(2-carboxyethyl)phenethylamino group.	2.42	2	0	adenosines; dicarboxylic acid monoamide; monocarboxylic acid	adenosine A2A receptor agonist; anti-inflammatory agent
ovalbumin Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.	2.03	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.	4.9	36	0	organic sodium salt	detergent; protein denaturant
mtt formazan MTT formazan: a blue MEM-insoluble mitochondrial byproduct; used to determine viability of cells with active mitochondrial dehydrogenase enzymes	2.03	1	0
l 663536 MK-886: orally active leukotriene biosynthesis inhibitor. 3-[3-(tert-butylsulfanyl)-1-(4-chlorobenzyl)-5-(propan-2-yl)-1H-indol-2-yl]-2,2-dimethylpropanoic acid : A member of the class of indoles that is 1H-indole substituted by a isopropyl group at position 5, a tert-butylsulfanediyl group at position 3, a 4-chlorobenzyl group at position 1 and a 2-carboxy-2-methylpropyl group at position 2. It acts as an inhibitor of arachidonate 5-lipoxygenase.	1.97	1	0	aryl sulfide; indoles; monocarboxylic acid; monochlorobenzenes	antineoplastic agent; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; leukotriene antagonist
2,4-dinitrophenylhydrazine 2,4-dinitrophenylhydrazine: structure. 2,4-dinitrophenylhydrazine : A C-nitro compound that is phenylhydrazine substituted at the 2- and 4-positions by nitro groups.	1.99	1	0	C-nitro compound; phenylhydrazines	reagent
zinc protoporphyrin ix [no description available]	2.05	1	0
alpha-chymotrypsin Chymotrypsin: A serine endopeptidase secreted by the pancreas as its zymogen, CHYMOTRYPSINOGEN and carried in the pancreatic juice to the duodenum where it is activated by TRYPSIN. It selectively cleaves aromatic amino acids on the carboxyl side.	3.05	5	0
empigen bb dodecylbetaine: RN given for chloride salt; RN for parent cpd not available 7/93	1.98	1	0
sc 560 SC560 : A member of the class of pyrazoles that is 1H-pyrazole which is substituted at positions 1, 3 and 5 by 4-methoxyphenyl, trifluoromethyl and 4-chlorophenyl groups, respectively. Unlike many members of the diaryl heterocycle class of cyclooxygenase (COX) inhibitors, SC-560 is selective for COX-1.	2.03	1	0	aromatic ether; monochlorobenzenes; organofluorine compound; pyrazoles	angiogenesis modulating agent; antineoplastic agent; apoptosis inducer; cyclooxygenase 1 inhibitor; non-steroidal anti-inflammatory drug
rhodamine 123 Rhodamine 123: A fluorescent probe with low toxicity which is a potent substrate for ATP BINDING CASSETTE TRANSPORTER, SUBFAMILY B, MEMBER 1 and the bacterial multidrug efflux transporter. It is used to assess mitochondrial bioenergetics in living cells and to measure the efflux activity of ATP BINDING CASSETTE TRANSPORTER, SUBFAMILY B, MEMBER 1 in both normal and malignant cells. (Leukemia 1997;11(7):1124-30). rhodamine 123(1+) : A cationic fluorescent dye derived from 9-phenylxanthene.	2.4	2	0	organic cation; xanthene dye	fluorochrome
petromyzonol sulfate petromyzonol sulfate: bile alocohol derivative that serves as a chemoattractant during the life cycle of sea lamprey (Petromyzon marinus)	2.02	1	0	steroid sulfate
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.	1.97	1	0	ethyl ester; maleate ester	glutathione depleting agent
catechin gallate catechin gallate: structure in first source. (+)-catechin-3-O-gallate : A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3S)-hydroxy group of (+)-catechin.	2.05	1	0	flavans; gallate ester; polyphenol	metabolite
sphingosine sphing-4-enine : A sphingenine in which the C=C double bond is located at the 4-position.. sphingenine : A 2-aminooctadecene-1,3-diol having (2S,3R)-configuration.. sphingoid : Sphinganine, its homologs and stereoisomers, and the hydroxy and unsaturated derivatives of these compounds.. 2-aminooctadec-4-ene-1,3-diol : A 2-aminooctadecene-1,3-diol having its double bond at position 4.	2.88	4	0	sphing-4-enine	human metabolite; mouse metabolite
quercetin [no description available]	4.55	7	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]	14.21	76	1	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.	5.31	55	0	prostaglandins E	human metabolite; mouse metabolite; oxytocic
dinoprost Dinoprost: A naturally occurring prostaglandin that has oxytocic, luteolytic, and abortifacient activities. Due to its vasocontractile properties, the compound has a variety of other biological actions.. prostaglandin F2alpha : A prostaglandins Falpha that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15. It is a naturally occurring prostaglandin used to induce labor.	3.23	6	0	monocarboxylic acid; prostaglandins Falpha	human metabolite; mouse metabolite
biochanin a [no description available]	2.04	1	0	4'-methoxyisoflavones; 7-hydroxyisoflavones	antineoplastic agent; EC 3.5.1.99 (fatty acid amide hydrolase) inhibitor; phytoestrogen; plant metabolite; tyrosine kinase inhibitor
tylosin [no description available]	2.45	2	0	aldehyde; disaccharide derivative; enone; leucomycin; macrolide antibiotic; monosaccharide derivative	allergen; bacterial metabolite; environmental contaminant; xenobiotic
apigenin Chamomile: Common name for several daisy-like plants (MATRICARIA; TRIPLEUROSPERMUM; ANTHEMIS; CHAMAEMELUM) native to Europe and Western Asia, now naturalized in the United States and Australia.	2.42	2	0	trihydroxyflavone	antineoplastic agent; metabolite
linoleic acid Linoleic Acid: A doubly unsaturated fatty acid, occurring widely in plant glycosides. It is an essential fatty acid in mammalian nutrition and is used in the biosynthesis of prostaglandins and cell membranes. (From Stedman, 26th ed). linoleic acid : An octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry.	2.96	4	0	octadecadienoic acid; omega-6 fatty acid	algal metabolite; Daphnia galeata metabolite; plant metabolite
calcitriol dihydroxy-vitamin D3: as a major in vitro metabolite of 1alpha,25-dihydroxyvitamin D3, produced in primary cultures of neonatal human keratinocytes	1.98	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
psychosine [no description available]	2.37	2	0	glycosylsphingoid	human metabolite
scopoletin [no description available]	3.05	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.	2.65	3	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.	3.11	5	0	carotenoid beta-end derivative; cyclic carotene	antioxidant; biological pigment; cofactor; ferroptosis inhibitor; human metabolite; mouse metabolite; plant metabolite; provitamin A
11-cis-retinal Rhodopsin: A purplish-red, light-sensitive pigment found in RETINAL ROD CELLS of most vertebrates. It is a complex consisting of a molecule of ROD OPSIN and a molecule of 11-cis retinal (RETINALDEHYDE). Rhodopsin exhibits peak absorption wavelength at about 500 nm.. 11-cis-retinal : A retinal having 2E,4Z,6E,8E-double bond geometry.	1.98	1	0	retinal	chromophore; human metabolite; mouse metabolite
leukotriene b4 Leukotriene B4: The major metabolite in neutrophil polymorphonuclear leukocytes. It stimulates polymorphonuclear cell function (degranulation, formation of oxygen-centered free radicals, arachidonic acid release, and metabolism). (From Dictionary of Prostaglandins and Related Compounds, 1990). leukotriene B4 : A leukotriene composed of (6Z,8E,10E,14Z)-icosatetraenoic acid having (5S)- and (12R)-hydroxy substituents. It is a lipid mediator of inflammation that is generated from arachidonic acid via the 5-lipoxygenase pathway.	2.68	3	0	dihydroxy monocarboxylic acid; hydroxy polyunsaturated fatty acid; leukotriene; long-chain fatty acid	human metabolite; mouse metabolite; plant metabolite; vasoconstrictor agent
leukotriene c4 Leukotriene C4: The conjugation product of LEUKOTRIENE A4 and glutathione. It is the major arachidonic acid metabolite in macrophages and human mast cells as well as in antigen-sensitized lung tissue. It stimulates mucus secretion in the lung, and produces contractions of nonvascular and some VASCULAR SMOOTH MUSCLE. (From Dictionary of Prostaglandins and Related Compounds, 1990). leukotriene C4 : A leukotriene that is (5S,7E,9E,11Z,14Z)-5-hydroxyicosa-7,9,11,14-tetraenoic acid in which a glutathionyl group is attached at position 6 via a sulfide linkage.	4.13	16	0	leukotriene	bronchoconstrictor agent; human metabolite; mouse metabolite
thromboxane a2 Thromboxane A2: An unstable intermediate between the prostaglandin endoperoxides and thromboxane B2. The compound has a bicyclic oxaneoxetane structure. It is a potent inducer of platelet aggregation and causes vasoconstriction. It is the principal component of rabbit aorta contracting substance (RCS).. thromboxane A2 : A thromboxane which is produced by activated platelets and has prothrombotic properties: it stimulates activation of new platelets as well as increases platelet aggregation.	2.9	4	0	epoxy monocarboxylic acid; thromboxanes A	mouse metabolite
retinol palmitate retinol palmitate: RN given refers to parent cpd; structure. retinyl palmitate : A palmitate ester of retinol with undefined geometry about the C=C bonds.. all-trans-retinyl palmitate : An all-trans-retinyl ester obtained by formal condensation of the carboxy group of palmitic (hexadecanoic acid) with the hydroxy group of all-trans-retinol. It is used in cosmetic products to treat various skin disorders such as acne, skin aging, wrinkles, dark spots, and also protect against psoriasis.	2.7	3	0	all-trans-retinyl ester; retinyl palmitate	antioxidant; Escherichia coli metabolite; human xenobiotic metabolite
hymecromone Hymecromone: A coumarin derivative possessing properties as a spasmolytic, choleretic and light-protective agent. It is also used in ANALYTICAL CHEMISTRY TECHNIQUES for the determination of NITRIC ACID.	3.57	9	0	hydroxycoumarin	antineoplastic agent; hyaluronic acid synthesis inhibitor
daphnetin [no description available]	2.1	1	0	hydroxycoumarin
alprostadil [no description available]	3.09	5	0	prostaglandins E	anticoagulant; human metabolite; platelet aggregation inhibitor; vasodilator agent
vitamin d 2 Ergocalciferols: Derivatives of ERGOSTEROL formed by ULTRAVIOLET RAYS breaking of the C9-C10 bond. They differ from CHOLECALCIFEROL in having a double bond between C22 and C23 and a methyl group at C24.. vitamin D2 : A vitamin D supplement and has been isolated from alfalfa.	1.96	1	0	hydroxy seco-steroid; seco-ergostane; vitamin D	bone density conservation agent; nutraceutical; plant metabolite; rodenticide
stigmasterol stigmasta-5,22-dien-3-ol: isolated from freeze-dried powder of Blackberries (Rubus ursinus L.) which showed an activity on inhibition of chemocarcinogen. stigmasterol : A 3beta-sterol that consists of 3beta-hydroxystigmastane having double bonds at the 5,6- and 22,23-positions.	1.99	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; phytosterols; stigmastane sterol	plant metabolite
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.	4.13	6	0	D3 vitamins; hydroxy seco-steroid; seco-cholestane; secondary alcohol; steroid hormone	geroprotector; human metabolite
rutin Hydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders.	1.99	1	0	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite
bilirubin diglucuronide [no description available]	4	4	0
leukotriene d4 Leukotriene D4: One of the biologically active principles of SRS-A. It is generated from LEUKOTRIENE C4 after partial hydrolysis of the peptide chain, i.e., cleavage of the gamma-glutamyl portion. Its biological actions include stimulation of vascular and nonvascular smooth muscle, and increases in vascular permeability. (From Dictionary of Prostaglandins and Related Compounds, 1990). leukotriene D4 : A leukotriene that is (7E,9E,11Z,14Z)-icosa-7,9,11,14-tetraenoic acid substituted by a hydroxy group at position 5 (5S) and a L-cysteinylglycinyl group at position 6 (6R).	1.99	1	0	dipeptide; leukotriene; organic sulfide	bronchoconstrictor agent; human metabolite; mouse metabolite
leukotriene e4 Leukotriene E4: A biologically active principle of SRS-A that is formed from LEUKOTRIENE D4 via a peptidase reaction that removes the glycine residue. The biological actions of LTE4 are similar to LTC4 and LTD4. (From Dictionary of Prostaglandins and Related Compounds, 1990). leukotriene E4 : A leukotriene that is (7E,9E,11Z,14Z)-icosa-7,9,11,14-tetraenoic acid substituted by a hydroxy group at position 5 (5S) and an L-cystein-S-yl group at position 6 (6R).	2.69	3	0	amino dicarboxylic acid; L-cysteine thioether; leukotriene; non-proteinogenic L-alpha-amino acid; secondary alcohol
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.	4	14	0	prostaglandins Falpha	human metabolite; mouse metabolite
senecionine senecionine: RN given refers to parent cpd; structure. senecionine : A pyrrolizidine alkaloid isolated from the plant species of the genus Senecio.	2.41	1	0	lactone; pyrrolizidine alkaloid; tertiary alcohol	plant metabolite
lipoxin a4 lipoxin A4: an antifibrolytic agent; structure given in first source; a role in ASPIRIN antiinflammatory activity. lipoxin A4 : A C20 hydroxy fatty acid having (5S)-, (6R)- and (15S)-hydroxy groups as well as (7E)- (9E)-, (11Z)- and (13E)-double bonds.	2.48	2	0	hydroxy polyunsaturated fatty acid; lipoxin; long-chain fatty acid	human metabolite; metabolite
alpha-linolenic acid linolenic acid : A two-membered subclass of octadecatrienoic acid comprising the (9Z,12Z,15Z)- and (6Z,9Z,12Z)-isomers. Linolenic acids are nutrients essential to the formation of prostaglandins and are also used in making paints and synthetic resins.. linolenate : A polyunsaturated fatty acid anion obtained by deprotonation of the carboxy group of either alpha- or gamma-linolenic acid.	1.98	1	0	linolenic acid; omega-3 fatty acid	micronutrient; mouse metabolite; nutraceutical
prostaglandin e3 prostaglandin E3: Structure	2.01	1	0	prostaglandins E	human metabolite
prostaglandin f1 prostaglandin F1: was EN to PROSTAGLANDINS F (75-81); RN given refers to (9 alpha,11 alpha,13E,15S)-isomer	1.99	1	0	prostaglandins Falpha	human metabolite
harmine Harmine: Alkaloid isolated from seeds of PEGANUM HARMALA; ZYGOPHYLLACEAE. It is identical to banisterine, or telepathine, from Banisteria caapi and is one of the active ingredients of hallucinogenic drinks made in the western Amazon region from related plants. It has no therapeutic use, but (as banisterine) was hailed as a cure for postencephalitic PARKINSON DISEASE in the 1920's.. harmine : A harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7.	2.38	2	0	harmala alkaloid	anti-HIV agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; metabolite
genistein [no description available]	2.96	4	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.	2.05	1	0	antibiotic antifungal drug; macrolide antibiotic; polyene antibiotic	antiamoebic agent; antiprotozoal drug; bacterial metabolite
clavulanic acid Clavulanic Acid: A beta-lactam antibiotic produced by the actinobacterium Streptomyces clavuligerus. It is a suicide inhibitor of bacterial beta-lactamase enzymes. Administered alone, it has only weak antibacterial activity against most organisms, but given in combination with other beta-lactam antibiotics it prevents antibiotic inactivation by microbial lactamase.. clavulanate : The conjugate base of clavulanic acid.. clavulanic acid : Antibiotic isolated from Streptomyces clavuligerus. It acts as a suicide inhibitor of bacterial beta-lactamase enzymes.	2	1	0	oxapenam	antibacterial drug; anxiolytic drug; bacterial metabolite; EC 3.5.2.6 (beta-lactamase) inhibitor
pulmicort Budesonide: A glucocorticoid used in the management of ASTHMA, the treatment of various skin disorders, and allergic RHINITIS.. budesonide : A glucocorticoid steroid having a highly oxygenated pregna-1,4-diene structure. It is used mainly in the treatment of asthma and non-infectious rhinitis and for treatment and prevention of nasal polyposis.	2.46	2	0	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; cyclic acetal; glucocorticoid; primary alpha-hydroxy ketone	anti-inflammatory drug; bronchodilator agent; drug allergen
olopatadine [no description available]	2.06	1	0
fucoxanthin fucoxanthin: RN given refers to (3S,3'S,5R,5'R,6S,6'R)-isomer. fucoxanthin : An epoxycarotenol that is found in brown seaweed and which exhibits anti-cancer, anti-diabetic, anti-oxidative and neuroprotective properties.	2.11	1	0
cembrene a cembrene A: RN refers to (R-(E,E,E))-isomer; isolated from paracloacal glands of the Chinese alligator (Alligator sinensis); structure given in first source. (R)-cembrene A : A fourteen-membered macrocyclic diterpene consisting of 1,5,9-trimethyl-12-(prop-1-en-2-yl)cyclotetradecane having three endocyclic double bonds located at positions 1, 5 and 9.	2.05	1	0	cycloalkatriene; diterpene; macrocycle	animal metabolite; bacterial metabolite; coral metabolite
harman harman: a beta-carboline; RN given refers to parent cpd; structure. harman : An indole alkaloid fundamental parent with a structure of 9H-beta-carboline carrying a methyl substituent at C-1. It has been isolated from the bark of Sickingia rubra, Symplocus racemosa, Passiflora incarnata, Peganum harmala, Banisteriopsis caapi and Tribulus terrestris, as well as from tobacco smoke. It is a specific, reversible inhibitor of monoamine oxidase A.	1.98	1	0	harmala alkaloid; indole alkaloid fundamental parent; indole alkaloid	anti-HIV agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; plant metabolite
7-hydroxycoumarin 7-oxycoumarin: derivatives have anti-oxidant properties. umbelliferone : A hydroxycoumarin that is coumarin substituted by a hydroxy group ay position 7.	2.41	2	0	hydroxycoumarin	fluorescent probe; food component; plant metabolite
baicalein [no description available]	2.17	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.	2.04	1	0	7-hydroxyflavonol; dihydroxyflavone	anti-inflammatory agent; antineoplastic agent; antioxidant; EC 2.7.11.18 (myosin-light-chain kinase) inhibitor; hepatoprotective agent; plant 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.	2.46	2	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
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.	2.07	1	0	coumestans; delta-lactone; polyphenol	anti-inflammatory agent; antioxidant; plant metabolite
daidzein [no description available]	2.43	2	0	7-hydroxyisoflavones	antineoplastic agent; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; phytoestrogen; plant metabolite
retrorsine retrorsine: RN given refers to cpd without isomeric designation; structure	2.41	1	0	macrolide
caffeic acid phenethyl ester phenethyl caffeate : An alkyl caffeate ester in which 2-phenylethyl is the alkyl component.	2.49	2	0	alkyl caffeate ester	anti-inflammatory agent; antibacterial agent; antineoplastic agent; antioxidant; antiviral agent; immunomodulator; metabolite; neuroprotective agent
rosmarinic acid rosmarinic acid: RN given refers to parent cpd; promote OT project. (R)-rosmarinic acid : A stereoisomer of rosmarinic acid having (R)-configuration.. rosmarinic acid : The 1-carboxy-2-(2,4-dihydroxyphenyl)ethyl ester of trans-caffeic acid.	2.11	1	0	rosmarinic acid	geroprotector; plant metabolite
rottlerin rottlerin: an angiogenesis inhibitor; an inhibitor of protein kinase Cdelta (PKCdelta) and calmodulin kinase III; RN refers to (E)-isomer; do not confuse this chalcone with an anthraquinone that is also called rottlerin (RN 481-72-1);. rottlerin : A chromenol that is 2,2-dimethyl-2H-chromene substituted by hydroxy groups at positions 5 and 7, a 3-acetyl-2,4,6-trihydroxy-5-methylbenzyl group at position 6 and a (1E)-3-oxo-1-phenylprop-1-en-3-yl group at position 8. A potassium channel opener, it is isolated from Mallotus philippensis.	2.04	1	0	aromatic ketone; benzenetriol; chromenol; enone; methyl ketone	anti-allergic agent; antihypertensive agent; antineoplastic agent; apoptosis inducer; K-ATP channel agonist; metabolite
flupenthixol cis-flupenthixol : A flupenthixol in which the double bond adopts a cis-configuration.	2.46	2	0	flupenthixol	dopaminergic antagonist
sdz psc 833 valspodar: nonimmunosuppressive cyclosporin analog which is a potent multidrug resistance modifier; 7-10 fold more potent than cyclosporin A; a potent P glycoprotein inhibitor; MW 1215	3.1	5	0	homodetic cyclic peptide
estradiol-17 beta-glucuronide 17beta-estradiol 17-glucosiduronic acid : A steroid glucosiduronic acid that consists of 17beta-estradiol having a beta-glucuronyl residue attached at position 17 via a glycosidic linkage.	5.85	30	0	3-hydroxy steroid; steroid glucosiduronic acid
l 660,711 [no description available]	3.41	7	0	quinolines
coenzyme q10 coenzyme Q10: Ubiquinone ring with a chain of 10 isoprene units; redox equilibrium with ubiqunol serving in mitochondrial inner membrane to transfer electrons; presence during reconstitution of acetylcholine receptor into phospholipid vesicles yields vesicles active in catalyzing carbamylcholine-sensitive Na+ flux; coenzyme Q10 depletion has been noted with use of statins. coenzyme Q10 : A ubiquinone having a side chain of 10 isoprenoid units. In the naturally occurring isomer, all isoprenyl double bonds are in the E- configuration.	3.4	1	1	ubiquinones	antioxidant; ferroptosis inhibitor; human metabolite
anandamide anandamide : An N-acylethanolamine 20:4 resulting from the formal condensation of carboxy group of arachidonic acid with the amino group of ethanolamine.	2.02	1	0	endocannabinoid; N-acylethanolamine 20:4	human blood serum metabolite; neurotransmitter; vasodilator agent
hr 780 HR 780: structure given in first source	1.98	1	0	phenylpyridine
lafutidine lafutidine: structure given in first source	2.41	2	0	organic molecular entity
josamycin [no description available]	2.03	1	0	acetate ester; aldehyde; disaccharide derivative; glycoside; macrolide antibiotic; tertiary alcohol; tertiary amino compound	antibacterial drug; metabolite
gefarnate Gefarnate: A water insoluble terpene fatty acid used in the treatment of gastrointestinal ulcers; it facilitates the healing and function of mucosal tissue.	2.38	2	0	organic molecular entity
geranylgeranylacetone geranylgeranylacetone: structure in first source; RN given refers to isomeric cpd without isomeric designation; mixture of (5E,9E,13E) & (5Z,9E,13E)-isomers. teprenone : A terpene ketone in which a (9E,13E)-geranylgernayl group is bonded to one of the alpha-methyls of acetone (it is a mixture of 5E- and 5Z-geoisomers in a 3:2 ratio).	7.38	2	0
sofalcone sofalcone : A member of the class of chalcones that is benzene in which the hydrogens at positions 1,2 and 5 are replaced by carboxymethoxy, (1E)-1-{4-[(3-methylbut-2-en-1-yl)oxy]phenyl}-3-oxoprop-1-en-3-yl, and (3-methylbut-2-en-1-yl)oxy groups, respectively. It is a gastrointestinal drug currently used for treatment of gastritis and gastric ulcers in Japan and South Korea.	3.07	5	0	aromatic ether; chalcones; monocarboxylic acid	anti-ulcer drug; antibacterial agent; gastrointestinal drug; plant metabolite
tranilast tranilast: antiallergic drug; potent inhibitor of homologous passive cutaneous anaphylaxis. tranilast : An amidobenzoic acid that is anthranilic acid in which one of the anilino hydrogens is replaced by a 3,4-dimethoxycinnamoyl group.	2.04	1	0	amidobenzoic acid; cinnamamides; dimethoxybenzene; secondary carboxamide	anti-allergic agent; anti-asthmatic drug; antineoplastic agent; aryl hydrocarbon receptor agonist; calcium channel blocker; hepatoprotective agent; nephroprotective agent
4-acetamido-4'-isothiocyanatostilbene-2,2'-disulfonic acid 4-Acetamido-4'-isothiocyanatostilbene-2,2'-disulfonic Acid: A non-penetrating amino reagent (commonly called SITS) which acts as an inhibitor of anion transport in erythrocytes and other cells.	3.22	6	0	stilbenoid
4,4'-dinitro-2,2'-stilbenedisulfonic acid 4,4'-dinitro-2,2'-stilbenedisulfonic acid: RN given refers to parent cpd without isomeric designation	2	1	0	4,4'-dinitrostilbene-2,2'-disulfonic acid
misoprostol Misoprostol: A synthetic analog of natural prostaglandin E1. It produces a dose-related inhibition of gastric acid and pepsin secretion, and enhances mucosal resistance to injury. It is an effective anti-ulcer agent and also has oxytocic properties.. misoprostol : A diastereoisomeric mixture composed of approximately equal amounts of a double racemate of four of the sixteen possible diastereoisomers of methyl (13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate that is racemic prostaglandin E1 which is lacking the hydroxy group at position 15, but which has an additional hydroxy group at position 16. It is a synthetic prostaglandin E1 analogue, used in the treatment of gastric and duodenal ulcers. A weak abortifacient, it is also used for cervical ripening prior to surgical termination of pregnancy. The (11R,16S)-diastereoisomer is the pharmacologically active form.	2.37	2	0
indocyanine green [no description available]	2.04	1	0	1,1-diunsubstituted alkanesulfonate; benzoindole; cyanine dye
ozagrel ozagrel: RN refers to (E)-isomer	2.39	2	0	cinnamic acids
pitavastatin pitavastatin : A dihydroxy monocarboxylic acid that is (6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]hept-6-enoic acid in which the two hydroxy groups are located at positions 3 and 5 (the 3R,5S-stereoisomer). Used as its calcium salt for treatment of hypercholesterolemia (elevated levels of cholesterol in the blood) on patients unable to sufficiently lower their cholesterol levels by diet and exercise.	2.96	4	0	cyclopropanes; dihydroxy monocarboxylic acid; monofluorobenzenes; quinolines; statin (synthetic)	antioxidant
16,16-dimethylprostaglandin e 16,16-dimethylprostaglandin E: RN given refers to (11alpha,13E,15R)-isomer	2.66	3	0	prostanoid
arbaprostil Arbaprostil: A synthetic prostaglandin E analog that protects the gastric mucosa, prevents ulceration, and promotes healing of peptic ulcers. The protective effect is independent of acid inhibition. It is also a potent inhibitor of pancreatic function and can inhibit the growth of experimental tumors.	2.37	2	0	prostanoid
16,16-dimethylprostaglandin e2 16,16-Dimethylprostaglandin E2: A synthetic prostaglandin E analog that protects the gastric mucosa, prevents ulceration, and promotes the healing of peptic ulcers. The protective effect is independent of acid inhibition. It is also a potent inhibitor of pancreatic function and growth of experimental tumors.. 16,16-dimethylprostaglandin E2 : A prostanoid that is prostaglandin E2 in which both of the hydrogens at position 16 have been replaced by methyl groups. A synthetic analogue of prostaglandin E2, it is a potent inhibitor of pancreatic function and growth of experimental tumors. It also protects the gastric mucosa, prevents ulceration, and promotes the healing of peptic ulcers.	3.58	9	0	cyclopentanones; monocarboxylic acid; prostanoid; secondary allylic alcohol	anti-ulcer drug; gastrointestinal drug; radiation protective agent
2,3-dinor-6-ketoprostaglandin f1alpha 2,3-dinor-6-ketoprostaglandin F1alpha: formed from 6-keto-PGF1alpha by Mycobacterium rhodochrous; RN given refers to (1R-(1alph,2beta(1E,3S*)))-isomer; structure given in first source. 2,3-dinor-6-oxoprostaglandin F1alpha : A prostanoid that is prostaglandin F1alpha lacking two methylenes in the carboxyalkyl chain and bearing an oxo group at the 6-position.	1.98	1	0	4-oxo monocarboxylic acid; prostanoid; secondary alcohol	metabolite
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.	4.13	16	0	thromboxanes B	human metabolite; mouse metabolite
2,3-dinor-thromboxane b2 [no description available]	1.98	1	0	thromboxane
4-hydroxy-2-nonenal 4-hydroxy-2-nonenal: cytotoxic product from peroxidation of liver microsomal lipids; RN given refers to cpd without isomeric designation. 4-hydroxynon-2-enal : An enal consisting of non-2-ene having an oxo group at the 1-position and a hydroxy group at the 4-position.. 4-hydroxynonenal : A monounsaturated fatty aldehyde that is nonanal that has undergone dehydrogenation to introduce a double bond at any position in the aliphatic chain and in which a hydrogen at position 4 has been replaced by a hydroxy group.	2.4	2	0	4-hydroxynon-2-enal; 4-hydroxynonenal
1-monooleoyl-rac-glycerol Peceol: lipid excipient containing readily dispersible mixture of mono- & diglycerides of oleic acid. 1-oleoylglycerol : A 1-monoglyceride where the acyl group is oleoyl.. monooleoylglycerol : A monoglyceride in which the acyl group is oleoyl with the position of acylation unspecified.	3.78	11	0	1-acylglycerol 18:1; monooleoylglycerol	plant metabolite
menaquinone 6 menaquinone 6: RN given refers to (all-E)-isomer	2.05	1	0
cholesteryl oleate cholesteryl oleate: RN given refers to ((Z)-isomer). cholesteryl oleate : The (Z)-stereoisomer of cholesteryl octadec-9-enoate.	3.23	6	0	CE(18:1); cholesteryl octadec-9-enoate	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.	3.41	7	0	5beta-cholanic acids; 6alpha,20xi-murideoxycholic acid; bile acid; C24-steroid	human metabolite; mouse metabolite
3-ketolithocholic acid 3-ketolithocholic acid: structure in first source	2.04	1	0	oxo-5beta-cholanic acid
cyclosporine ramihyphin A: one of the metabolites produced by Fusarium sp. S-435; RN given refers to cpd with unknown MF	5.2	15	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
acrivastine acrivastine: a second generation antihistamine. acrivastine : A member of the class of pyridines that is (pyridin-2-yl)acrylic acid substituted at position 6 by a [(1E)-1-(4-methylphenyl)-3-(pyrrolidin-1-yl)prop-1-en-1-yl group. It is a non-sedating antihistamine used for treatment of hayfever, urticaria, and rhinitis.	2.06	1	0	alpha,beta-unsaturated monocarboxylic acid; N-alkylpyrrolidine; olefinic compound; pyridines	H1-receptor antagonist
granisetron Granisetron: A serotonin receptor (5HT-3 selective) antagonist that has been used as an antiemetic for cancer chemotherapy patients.. granisetron : A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of 1-methyl-1H-indazole-3-carboxylic acid with the primary amino group of (3-endo)-9-methyl-9-azabicyclo[3.3.1]nonan-3-amine. A selective 5-HT3 receptor antagonist, it is used (generally as the monohydrochloride salt) to manage nausea and vomiting caused by cancer chemotherapy and radiotherapy, and to prevent and treat postoperative nausea and vomiting.	1.99	1	0	aromatic amide; indazoles
ly 163892 loracarbef: 1-carbacephem antibiotic; has a broad spectrum of antimicrobial activity; structure given in first source; carbacephems differ from cephalosporins in the substitution of a sulfur atom in the dihydrothiazine ring with a methylene group to form a tetrahydropyridine ring. loracarbef : A synthetic "carba" analogue of cefaclor, with carbon replacing sulfur at position 1. Used to treat a wide range of infections caused by both gram-positive and gram-negative bacteria.	2.06	1	0	carbacephem; zwitterion	antibacterial drug; antimicrobial agent
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.	2.7	3	0	morphinane alkaloid; organic heteropentacyclic compound; tertiary alcohol	antidote to opioid poisoning; central nervous system depressant; mu-opioid receptor antagonist
vitamin k 1 Vitamin K 1: A family of phylloquinones that contains a ring of 2-methyl-1,4-naphthoquinone and an isoprenoid side chain. Members of this group of vitamin K 1 have only one double bond on the proximal isoprene unit. Rich sources of vitamin K 1 include green plants, algae, and photosynthetic bacteria. Vitamin K1 has antihemorrhagic and prothrombogenic activity.. phylloquinone : A member of the class of phylloquinones that consists of 1,4-naphthoquinone having methyl and phytyl groups at positions 2 and 3 respectively. The parent of the class of phylloquinones.	2.36	2	0	phylloquinones; vitamin K	cofactor; human metabolite; plant metabolite
proscillaridin Proscillaridin: A cardiotonic glycoside isolated from Scilla maritima var. alba (Squill).	2.06	1	0	organic molecular entity
sirolimus Sirolimus: A macrolide compound obtained from Streptomyces hygroscopicus that acts by selectively blocking the transcriptional activation of cytokines thereby inhibiting cytokine production. It is bioactive only when bound to IMMUNOPHILINS. Sirolimus is a potent immunosuppressant and possesses both antifungal and antineoplastic properties.. sirolimus : A macrolide lactam isolated from Streptomyces hygroscopicus consisting of a 29-membered ring containing 4 trans double bonds, three of which are conjugated. It is an antibiotic, immunosupressive and antineoplastic agent.	2.71	3	0	antibiotic antifungal drug; cyclic acetal; cyclic ketone; ether; macrolide lactam; organic heterotricyclic compound; secondary alcohol	antibacterial drug; anticoronaviral agent; antineoplastic agent; bacterial metabolite; geroprotector; immunosuppressive agent; mTOR inhibitor
brefeldin a [no description available]	2.91	4	0	macrolide antibiotic	Penicillium metabolite
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.	3.08	5	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
demycarosylturimycin h [no description available]	2.04	1	0
iloprost Iloprost: An eicosanoid, derived from the cyclooxygenase pathway of arachidonic acid metabolism. It is a stable and synthetic analog of EPOPROSTENOL, but with a longer half-life than the parent compound. Its actions are similar to prostacyclin. Iloprost produces vasodilation and inhibits platelet aggregation.. iloprost : A carbobicyclic compound that is prostaglandin I2 in which the endocyclic oxygen is replaced by a methylene group and in which the (1E,3S)-3-hydroxyoct-1-en-1-yl side chain is replaced by a (3R)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl group. A synthetic analogue of prostacyclin, it is used as the trometamol salt (generally by intravenous infusion) for the treatment of peripheral vascular disease and pulmonary hypertension.	2.93	4	0	carbobicyclic compound; monocarboxylic acid; secondary alcohol	platelet aggregation inhibitor; vasodilator agent
lysophosphatidic acid lysophosphatidic acid: RN given refers to parent cpd. 1-oleoyl-sn-glycerol 3-phosphate : A 1-acyl-sn-glycerol 3-phosphate having oleoyl as the 1-O-acyl group.. lysophosphatidic acid : A member of the class of lysophosphatidic acids obtained by hydrolytic removal of one of the two acyl groups of any phosphatidic acid. A 'closed' class.	2.54	2	0	1-acyl-sn-glycerol 3-phosphate
lysophosphatidylcholines lysophosphatidylcholine : An acylglycerophosphocholine resulting from partial hydrolysis of a phosphatidylcholine, which removes one of the fatty acyl groups. The structure is depicted in the image where R1 = acyl, R2 = H or where R1 = H, R2 = acyl.	4.46	23	0	1-O-acyl-sn-glycero-3-phosphocholine
cytochalasin b Cytochalasin B: A cytotoxic member of the CYTOCHALASINS.. cytochalasin B : An organic heterotricyclic compound, that is a mycotoxin which is cell permeable an an inhibitor of cytoplasmic division by blocking the formation of contractile microfilaments.	2.89	4	0	cytochalasin; lactam; lactone; organic heterotricyclic compound	actin polymerisation inhibitor; metabolite; mycotoxin; platelet aggregation inhibitor
calyculin a calyculin A: RN given refers to (5S-(5alpha(2R(1S,3S,4S,5R,6R,7E,9E,11E,13Z),3R),7beta(E(S)),*beta,9alpha))-isomer	1.98	1	0
seglitide seglitide: more potent than somatostatin for inhibition of insulin, glucagon & growth hormone release; used experimentally in treatment of Alzheimer's disease; somatostatin receptor antagonist	2.04	1	0
biliverdine [no description available]	2.67	3	0
spiraeoside spiraeoside: from flowers of Filipendula ulmaria (L.); structure given in first source. quercetin 4'-O-beta-D-glucopyranoside : A quercetin O-glucoside that is quercetin with a beta-D-glucosyl residue attached at position 4'.	1.99	1	0	beta-D-glucoside; flavonols; monosaccharide derivative; quercetin O-glucoside; tetrahydroxyflavone	antineoplastic agent; antioxidant; plant 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.	2.07	1	0	(trifluoromethyl)benzenes; 5-methoxyvalerophenone O-(2-aminoethyl)oxime	antidepressant; anxiolytic drug; serotonin uptake inhibitor
ergosterol-5,8-peroxide ergosterol-5,8-peroxide: also inhibits sulfatase; isolated from fungus Cercospora kikuchii; structure given in first source. ergosterol peroxide : An ergostanoid that is ergosta-6,22-dien-3-ol with a peroxy group between positions 5 and 8 (the 3beta,5alpha,8alpha,22E stereoisomer). Isolated from Ganoderma lucidum and Cordyceps sinensis, it exhibits antimycobacterial, trypanocidal and antineoplastic activities.	3.51	1	0	3beta-sterol; ergostanoid; organic peroxide; phytosterols	antimycobacterial drug; antineoplastic agent; metabolite; trypanocidal drug
lead Lead: A soft, grayish metal with poisonous salts; atomic number 82, atomic weight 207.2, symbol Pb.	1.96	1	0	carbon group element atom; elemental lead; metal atom	neurotoxin
sulindac sulfide sulindac sulfide: sulfated analog of indomethacin & inhibitor of prostaglandin synthesis in vitro; RN given refers to cpd without isomeric designation; structure given in first source. sulindac sulfide : An aryl sulfide that is a metabolite of sulindac. A non-steroidal anti-inflammatory drug, which also has anticancer activity.	2.05	1	0	aryl sulfide; monocarboxylic acid; organofluorine compound	antineoplastic agent; apoptosis inducer; non-steroidal anti-inflammatory drug
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)	1.98	1	0
15-hydroxy-5,8,11,13-eicosatetraenoic acid 15-hydroxy-5,8,11,13-eicosatetraenoic acid: potent & selective inhibitor of platelet lipoxygenase; RN given refers to cpd without isomeric designation	1.98	1	0
(6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid (6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid : A dihydroxy monocarboxylic acid that is N-isopropylindole which is substituted at position 3 by a p-fluorophenyl group and at position 2 by a 6-carboxy-3,5-dihydroxyhex-1-en-1-yl group. It has four possible diastereoisomers.	2.47	2	0	dihydroxy monocarboxylic acid; indoles; organofluorine compound
barium Barium: An element of the alkaline earth group of metals. It has an atomic symbol Ba, atomic number 56, and atomic weight 138. All of its acid-soluble salts are poisonous.	1.95	1	0	alkaline earth metal atom; elemental barium
rubidium Rubidium: An element that is an alkali metal. It has an atomic symbol Rb, atomic number 37, and atomic weight 85.47. It is used as a chemical reagent and in the manufacture of photoelectric cells.	2.65	3	0	alkali metal atom
aluminum Aluminum: A metallic element that has the atomic number 13, atomic symbol Al, and atomic weight 26.98.	3.34	7	0	boron group element atom; elemental aluminium; metal atom
arsenic Arsenic: A shiny gray element with atomic symbol As, atomic number 33, and atomic weight 75. It occurs throughout the universe, mostly in the form of metallic arsenides. Most forms are toxic. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), arsenic and certain arsenic compounds have been listed as known carcinogens. (From Merck Index, 11th ed)	3.31	2	0	metalloid atom; pnictogen	micronutrient
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.	2.07	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.	2.79	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
dextrorphan Dextrorphan: Dextro form of levorphanol. It acts as a noncompetitive NMDA receptor antagonist, among other effects, and has been proposed as a neuroprotective agent. It is also a metabolite of DEXTROMETHORPHAN.	2.6	1	0	morphinane alkaloid
lisinopril Lisinopril: One of the ANGIOTENSIN-CONVERTING ENZYME INHIBITORS (ACE inhibitors), orally active, that has been used in the treatment of hypertension and congestive heart failure.	2.75	3	0	dipeptide	EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor
batimastat batimastat: structure given in first source; a synthetic matrix metalloproteinase inhibitor. batimastat : A secondary carboxamide resulting from the formal condensation of the carboxy group of (2S,3R)-5-methyl-3-{[(2S)-1-(methylamino)-1-oxo-3-phenylpropan-2-yl]carbamoyl}-2-[(thiophen-2-ylsulfanyl)methyl]hexanoic acid with the amino group of hydroxylamine. It a broad-spectrum matrix metalloprotease inhibitor.	2.05	1	0	hydroxamic acid; L-phenylalanine derivative; organic sulfide; secondary carboxamide; thiophenes; triamide	angiogenesis inhibitor; antineoplastic agent; matrix metalloproteinase inhibitor
indinavir sulfate Indinavir: A potent and specific HIV protease inhibitor that appears to have good oral bioavailability.	2.46	2	0	dicarboxylic acid diamide; N-(2-hydroxyethyl)piperazine; piperazinecarboxamide	HIV protease inhibitor
sulfur Sulfur: An element that is a member of the chalcogen family. It has an atomic symbol S, atomic number 16, and atomic weight [32.059; 32.076]. It is found in the amino acids cysteine and methionine.	7.35	2	0	chalcogen; nonmetal atom	macronutrient
enalapril Enalapril: An angiotensin-converting enzyme inhibitor that is used to treat HYPERTENSION and HEART FAILURE.. enalapril : A dicarboxylic acid monoester that is ethyl 4-phenylbutanoate in which a hydrogen alpha to the carboxy group is substituted by the amino group of L-alanyl-L-proline (S-configuration).	4.37	6	0	dicarboxylic acid monoester; dipeptide	antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; geroprotector; prodrug
dimyristoylphosphatidylcholine 1,2-di-O-myristoyl-sn-glycero-3-phosphocholine : A 1,2-diacyl-sn-glycero-3-phosphocholine where the two phosphatidyl acyl groups are specified as tetradecanoyl (myristoyl).. dimyristoyl phosphatidylcholine : A phosphatidylcholine where the phosphatidyl acyl groups are specified as tetradecanoyl (myristoyl).	2.67	3	0	1,2-diacyl-sn-glycero-3-phosphocholine; phosphatidylcholine 28:0; tetradecanoate ester	antigen; mouse metabolite
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	5.49	21	0	cysteinium	fundamental metabolite
silicon Silicon: A trace element that constitutes about 27.6% of the earth's crust in the form of SILICON DIOXIDE. It does not occur free in nature. Silicon has the atomic symbol Si, atomic number 14, and atomic weight [28.084; 28.086].	2.36	2	0	carbon group element atom; metalloid atom; nonmetal atom
phosphorus Phosphorus: A non-metal element that has the atomic symbol P, atomic number 15, and atomic weight 31. It is an essential element that takes part in a broad variety of biochemical reactions.	3.23	6	0	monoatomic phosphorus; nonmetal atom; pnictogen	macronutrient
enalaprilat anhydrous Enalaprilat: The active metabolite of ENALAPRIL and one of the potent, intravenously administered, ANGIOTENSIN-CONVERTING ENZYME INHIBITORS. It is an effective agent for the treatment of essential hypertension and has beneficial hemodynamic effects in heart failure. The drug produces renal vasodilation with an increase in sodium excretion.. enalaprilat dihydrate : The dihydrate form of enalaprilat, an angiotensin-converting enzyme (ACE) inhibitor that is used (often in the form of its prodrug, enalapril) in the treatment of hypertension and heart failure, for reduction of proteinuria and renal disease in patients with nephropathies, and for the prevention of stroke, myocardial infarction, and cardiac death in high-risk patients. Unlike enalapril, enalaprilat is not absorbed by mouth but is administered by intravenous injection.. enalaprilat (anhydrous) : Enalapril in which the ethyl ester group has been hydrolysed to the corresponding carboxylic acid. Enalaprilat is an angiotensin-converting enzyme (ACE) inhibitor and is used (often in the form of its prodrug, enalapril) in the treatment of hypertension and heart failure, for reduction of proteinuria and renal disease in patients with nephropathies, and for the prevention of stroke, myocardial infarction, and cardiac death in high-risk patients. Unlike enalapril, enalaprilat is not absorbed by mouth but is given by intravenous injection, usually as the dihydrate.	1.99	1	0	dicarboxylic acid; dipeptide	antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor
2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid 2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid: chromogen in glucose oxidase-peroxidase method for determining serum glucose; used in free radical scavenging assays; structure in first source	1.95	1	0
nitecapone nitecapone: structure given in first source	1.98	1	0	hydroxycinnamic acid
ditekiren ditekiren: orally active renin inhibitor	2	1	0
cefquinome cefquinome: broad spectrum antibiotic; RN given refers to (6R(6alpha,7beta(Z)-isomer); structure given in first source	2.13	1	0
zerumbone zerumbone: RN given for (E,E,E)-isomer; structure in first source. zerumbone : A sesquiterpenoid and cyclic ketone that is (1E,4E,8E)-alpha-humulene which is substituted by an oxo group at the carbon atom attached to two double bonds. It is obtained by steam distillation from a type of edible ginger, Zingiber zerumbet Smith, grown particularly in southeast Asia.	2.07	1	0	cyclic ketone; sesquiterpenoid	anti-inflammatory agent; glioma-associated oncogene inhibitor; plant metabolite
sulindac sulfone sulindac sulfone: inhibits K-ras-dependent cyclooxygenase-2; sulfated analog of indomethacin;; CP248 is an antineoplastic agent that fosters microtubule depolymerization; structure in first source. sulindac sulfone : A sulfone metabolite of sulindac that inhibits cell growth by inducing apoptosis independently of cyclooxygenase inhibition. It inhibits the development and induces regression of premalignant adenomatous polyps. Lipoxygenase and Cox-2 inhibitor.	2.45	2	0	monocarboxylic acid; organofluorine compound; sulfone	apoptosis inducer; cyclooxygenase 2 inhibitor; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor
alanyl-alanyl-alanyl-alanine alanyl-alanyl-alanyl-alanine: RN given refers to (L)-isomer	2.01	1	0
cefuroxime [no description available]	2.06	1	0	3-(carbamoyloxymethyl)cephalosporin; furans; oxime O-ether	drug allergen
ceftriaxone [no description available]	2.06	1	0	1,2,4-triazines; 1,3-thiazoles; cephalosporin; oxime O-ether	antibacterial drug; drug allergen; EC 3.5.2.6 (beta-lactamase) inhibitor
ceftazidime [no description available]	2.04	1	0	cephalosporin; oxime O-ether	antibacterial drug; drug allergen; EC 2.4.1.129 (peptidoglycan glycosyltransferase) inhibitor
penicillin v [no description available]	1.99	1	0	1,1'-diethyl-2,2'-cyanine; quinolines
enkephalin, ala(2)-mephe(4)-gly(5)- Enkephalin, Ala(2)-MePhe(4)-Gly(5)-: An enkephalin analog that selectively binds to the MU OPIOID RECEPTOR. It is used as a model for drug permeability experiments.	2.03	1	0
strontium radioisotopes Strontium Radioisotopes: Unstable isotopes of strontium that decay or disintegrate spontaneously emitting radiation. Sr 80-83, 85, and 89-95 are radioactive strontium isotopes.	2.35	2	0
tyrosyl-alanyl-glycine tyrosyl-alanyl-glycine: RN given refers to unlabeled (L-Tyr-D-Ala)-isomer	2.01	1	0
triolein Triolein: (Z)-9-Octadecenoic acid 1,2,3-propanetriyl ester.. triolein : A triglyceride formed by esterification of the three hydroxy groups of glycerol with oleic acid. Triolein is one of the two components of Lorenzo's oil.	5.13	18	0	triglyceride	Caenorhabditis elegans metabolite; plant metabolite
guanabenz Guanabenz: An alpha-2 selective adrenergic agonist used as an antihypertensive agent.	2.06	1	0	dichlorobenzene
bafilomycin a [no description available]	2	1	0
carbocyanines Carbocyanines: Compounds that contain three methine groups. They are frequently used as cationic dyes used for differential staining of biological materials.	2.21	1	0	cyanine dye; organic iodide salt	fluorochrome
25-hydroxyvitamin d 2 25-Hydroxyvitamin D 2: 9,10-Secoergosta-5,7,10(19),22-tetraene-3,25-diol. Biologically active metabolite of vitamin D2 which is more active in curing rickets than its parent. The compound is believed to attach to the same receptor as vitamin D2 and 25-hydroxyvitamin D3.	1.96	1	0	hydroxycalciol; seco-ergostane; vitamin D	bone density conservation agent; human xenobiotic metabolite; nutraceutical
cinidon-ethyl Lotus: A genus of the PEA FAMILY. The genus Lotus, formerly known as Tetragonolobus, is unrelated to other plants with the common name of lotus (NELUMBO and NYMPHAEA).. cinidon ethyl : A carboxylic ester and organochlorine compound that is the ethyl ester of cinidon.	2.31	1	0	ethyl ester; isoindoles; monochlorobenzenes	herbicide
ammonium sulfate Ammonium Sulfate: Sulfuric acid diammonium salt. It is used in CHEMICAL FRACTIONATION of proteins.. ammonium sulfate : An inorganic sulfate salt obtained by reaction of sulfuric acid with two equivalents of ammonia. A high-melting (decomposes above 280degreeC) white solid which is very soluble in water (70.6 g/100 g water at 0degreeC; 103.8 g/100 g water at 100degreeC), it is widely used as a fertilizer for alkaline soils.	2.86	4	0	ammonium salt; inorganic sulfate salt	fertilizer
4,4'-diisothiocyanostilbene-2,2'-disulfonic acid 4,4'-Diisothiocyanostilbene-2,2'-Disulfonic Acid: An inhibitor of anion conductance including band 3-mediated anion transport.	3.68	10	0
menaquinone 9 menaquinone-9 : A menaquinone whose side-chain contains 9 isoprene units in an all-trans-configuration.	2.05	1	0	menaquinone	Escherichia coli metabolite
rifamycin sv rifamycin SV: RN given refers to parent cpd; structure in Merck Index, 9th ed, #8009. rifamycin SV : A member of the class of rifamycins that exhibits antibiotic and antitubercular properties.	3.52	8	0	acetate ester; cyclic ketal; lactam; macrocycle; organic heterotetracyclic compound; polyphenol; rifamycins	antimicrobial agent; antitubercular agent; bacterial metabolite
ro 42-5892 remikiren : An L-histidine derivative that is L-histidine in which one of the amino hydrogens is replaced by a (2S)-2-[(2-methylpropane-2-sulfonyl)methyl]-3-phenylpropanoyl group and the carboxy group is replaced by a [(2S,3R,4S)-1-cyclohexyl-4-cyclopropyl-3,4-dihydroxybutan-2-yl]amino group. It is a renin inhibitor which was under development for the treatment of hypertension (now discontinued).	2.06	1	0	cyclopropanes; diol; L-histidine derivative; secondary carboxamide; sulfone	antihypertensive agent; EC 3.4.23.15 (renin) inhibitor; peptidomimetic; vasodilator agent
tetrodotoxin Tetrodotoxin: An aminoperhydroquinazoline poison found mainly in the liver and ovaries of fishes in the order TETRAODONTIFORMES, which are eaten. The toxin causes paresthesia and paralysis through interference with neuromuscular conduction.. tetrodotoxin : A quinazoline alkaloid that is a marine toxin isolated from fish such as puffer fish. It has been shown to exhibit potential neutotoxicity due to its ability to block voltage-gated sodium channels.	2.91	4	0	azatetracycloalkane; oxatetracycloalkane; quinazoline alkaloid	animal metabolite; bacterial metabolite; marine metabolite; neurotoxin; voltage-gated sodium channel blocker
selenium Selenium: An element with the atomic symbol Se, atomic number 34, and atomic weight 78.97. It is an essential micronutrient for mammals and other animals but is toxic in large amounts. Selenium protects intracellular structures against oxidative damage. It is an essential component of GLUTATHIONE PEROXIDASE.	5.92	25	1	chalcogen; nonmetal atom	micronutrient
tellurium Tellurium: An element that is a member of the chalcogen family. It has the atomic symbol Te, atomic number 52, and atomic weight 127.60. It has been used as a coloring agent and in the manufacture of electrical equipment. Exposure may cause nausea, vomiting, and CNS depression.	2.86	4	0	chalcogen; metalloid atom
oxalates Oxalates: Derivatives of OXALIC ACID. Included under this heading are a broad variety of acid forms, salts, esters, and amides that are derived from the ethanedioic acid structure.	3.05	5	0
(3S,5S,6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid Fluvastatin: An indole-heptanoic acid derivative that inhibits HMG COA REDUCTASE and is used to treat HYPERCHOLESTEROLEMIA. In contrast to other statins, it does not appear to interact with other drugs that inhibit CYP3A4.. (3S,5S,6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid : A (6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid diastereoisomer in which both chiral centres have S configuration.. fluvastatin : A racemate comprising equimolar amounts of (3R,5S)- and (3S,5R)-fluvastatin. An HMG-CoA reductase inhibitor, it is used (often as the corresponding sodium salt) to reduce triglycerides and LDL-cholesterol, and increase HDL-chloesterol, in the treatment of hyperlipidaemia.	2.99	4	0	(6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid
cefatrizine Cefatrizine: Orally active semisynthetic cephalosporin antibiotic with broad-spectrum activity.. cefatrizine : A cephalosporin compound having (1H-1,2,3-triazol-4-ylsulfanyl)methyl and [(2R)-2-amino-2-(4-hydroxyphenyl)]acetamido side-groups. An antibacterial drug first prepared in the 1970s, it has more recently been found to be an inhibitor of eukaryotic elongation factor-2 kinase (eEF2K), which is known to regulate apoptosis, autophagy and ER stress in many types of human cancers.	2.06	1	0	amino acid amide; carboxylic acid; cephalosporin; phenols; semisynthetic derivative; triazoles	antibacterial drug; EC 2.7.11.20 (elongation factor 2 kinase) inhibitor
mevalonolactone mevalonolactone: RN given refers to unlabeled cpd without isomeric designation; structure. mevalonolactone : A racemate comprising equimolar amounts of (R)-mevalonolactone and (S)-mevalonolactone.	2.38	2	0	4-hydroxy-4-methyloxan-2-one	fungal metabolite; plant metabolite
antimycin a Antimycin A: An antibiotic substance produced by Streptomyces species. It inhibits mitochondrial respiration and may deplete cellular levels of ATP. Antimycin A1 has been used as a fungicide, insecticide, and miticide. (From Merck Index, 12th ed). antimycin A : A nine-membered bis-lactone having methyl substituents at the 2- and 6-positions, an n-hexyl substituent at the 8-position, an acyloxy substituent at the 7-position and an aroylamido substituent at the 3-position. It is produced by Streptomyces bacteria and has found commercial use as a fish poison.	2.37	2	0	amidobenzoic acid
cholestanol Cholestanol: A cholesterol derivative found in human feces, gallstones, eggs, and other biological matter.	2.66	3	0	cholestanoid
dolichols Dolichols: A class of polyprenols which contain approximately 20 isoprene residues. Although considered ISOPRENOIDS, they terminate with an alpha-saturated isoprenoid group at the hydroxy end of the molecule.	2.36	2	0	polyterpene
simethicone Simethicone: A poly(dimethylsiloxane) which is a polymer of 200-350 units of dimethylsiloxane, along with added silica gel. It is used as an antiflatulent, surfactant, and ointment base.	3.36	1	1
tiacrilast tiacrilast: structure given in first source	2.06	1	0
nileprost nileprost: stable prostacyclin analog; RN given refers to (E)-(3aR,4R,5R,6aS)(E)-(3S,4RS)-isomer	1.96	1	0
dehydroergosterol dehydroergosterol : A phytosterol consiting of ergostane having double bonds at the 5,6-, 7,8- 9,11- and 22,23-positions as well as a 3beta-hydroxy group.	2	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; ergostanoid; phytosterols	biomarker; metabolite
sarcophine sarcophine: toxic cembranolide phosphofructokinase inhibitor isolated from coral Sarcophyton glaucum; structure	2.05	1	0
1-(1-glycero)dodeca-1,3,5,7,9-pentaene 1-(1-glycero)dodeca-1,3,5,7,9-pentaene: fecapentaene mutagen of bacterial origin from human feces; structure given in first source	2	1	0
1-(1-glycero)tetradeca-1,3,5,7,9-pentaene 1-(1-glycero)tetradeca-1,3,5,7,9-pentaene: fecapentaene mutagen of bacterial origin from human feces; structure given in first source	2	1	0
2-methyl-3-(4-(3-pyridinylmethyl)phenyl)-2-propenoic acid 2-methyl-3-(4-(3-pyridinylmethyl)phenyl)-2-propenoic acid: RN refers to (E)-isomer	2.37	2	0
1-palmitoyl-2-linoleoylphosphatidylcholine [no description available]	1.98	1	0
op 2507 OP 2507: prostacyclin analog; structure given in first source	1.99	1	0
cholesteryl oleyl ether cholesteryl oleyl ether: not as rapidly degraded as the cholesterol esters; RN given refers to (3beta(Z))-isomer	2.39	2	0
1,2-linoleoylphosphatidylcholine 1,2-linoleoylphosphatidylcholine: used for premature induction of labor in rabbits; RN given refers to (all Z)-isomer	2.13	1	0
1-stearoyl-2-arachidonylphosphatidylcholine 1-stearoyl-2-arachidonylphosphatidylcholine: RN given refers to (all-Z)-isomer	1.98	1	0
4-o-methylascochlorin 4-O-methylascochlorin: causes unusual concentration of urine & prevents polydipsia in DOCA hypertensive rats; structure given in first source	1.96	1	0
16,16-dimethylprostaglandin f2alpha 16,16-dimethylprostaglandin F2alpha: RN given refers to (5Z,9alpha,11alpha,13E,15R)-isomer	1.96	1	0
sphingosyl beta-glucoside sphingosyl beta-glucoside: isolated from spleen in Gaucher's disease	1.96	1	0
bilirubin ditaurine bilirubin ditaurine: prevents the peroxyl radical-induced oxidation of phosphatidylcholine in either multimellar liposomes or miscelles	2.4	2	0
cdw17 antigen [no description available]	1.96	1	0
pregna-4,17-diene-3,16-dione, (17z)-isomer [no description available]	2.05	1	0
asialo gm1 ganglioside [no description available]	1.96	1	0
i(3)so3-galactosylceramide Sulfoglycosphingolipids: GLYCOSPHINGOLIPIDS with a sulfate group esterified to one of the sugar groups.. 1-(3-O-sulfo-beta-D-galactosyl)-N-tetracosanoylsphingosine : A D-galactosyl-N-acylsphingosine having a sulfo group at the 3-position on the galactose ring and tetracosanoyl as the N-acyl group.	3.06	5	0	galactosylceramide sulfate; N-acyl-beta-D-galactosylsphingosine
dirithromycin [no description available]	2.03	1	0	macrolide antibiotic	prodrug
azlocillin Azlocillin: A semisynthetic ampicillin-derived acylureido penicillin.. azlocillin : A semisynthetic penicillin having a 6beta-{(2R)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetyl}amino side-group. It is an antibiotic used in treating infections caused by Pseudomonas aeruginosa, Escherichia coli and Haemophilus influenzae.	1.96	1	0	penicillin allergen; penicillin; semisynthetic derivative	antibacterial drug
verlukast verlukast: LTD4 receptor antagonist	3.14	5	0
ceftizoxime [no description available]	3.15	1	0	cephalosporin	antibacterial drug
beta-escin [no description available]	3.46	8	0
s-nitroso-n-acetylpenicillamine S-Nitroso-N-Acetylpenicillamine: A sulfur-containing alkyl thionitrite that is one of the NITRIC OXIDE DONORS.	2.01	1	0	nitroso compound; nitrosothio compound	nitric oxide donor; vasodilator agent
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.	3.85	4	0	imidazolidine-2,4-dione; nitrofuran antibiotic; organonitrogen heterocyclic antibiotic; organooxygen heterocyclic antibiotic	antibacterial drug; antiinfective agent; hepatotoxic agent
ca 074 methyl ester [no description available]	2.01	1	0
gadolinium dtpa Gadolinium DTPA: A complex of gadolinium with a chelating agent, diethylenetriamine penta-acetic acid (DTPA see PENTETIC ACID), that is given to enhance the image in cranial and spinal MRIs. (From Martindale, The Extra Pharmacopoeia, 30th ed, p706)	2.92	4	0	gadolinium coordination entity	MRI contrast agent
sq-23377 Ionomycin: A divalent calcium ionophore that is widely used as a tool to investigate the role of intracellular calcium in cellular processes.. ionomycin : A very long-chain fatty acid that is docosa-10,16-dienoic acid which is substituted by methyl groups at positions 4, 6, 8, 12, 14, 18 and 20, by hydroxy groups at positions 11, 19 and 21, and by a (2',5-dimethyloctahydro-2,2'-bifuran-5-yl)ethanol group at position 21. An ionophore produced by Streptomyces conglobatus, it is used in research to raise the intracellular level of Ca(2+) and as a research tool to understand Ca(2+) transport across biological membranes.	2.9	4	0	cyclic ether; enol; polyunsaturated fatty acid; very long-chain fatty acid	calcium ionophore; metabolite
roxithromycin (E)-roxithromycin : A major geometrical isomer of roxithromycin.	2.03	1	0	roxithromycin	environmental contaminant; xenobiotic
enkephalin, leucine-2-alanine Enkephalin, Leucine-2-Alanine: A delta-selective opioid (ANALGESICS, OPIOID). It can cause transient depression of mean arterial blood pressure and heart rate.	2.42	2	0
nocloprost nocloprost: phalloidin transport inhibitor	2.37	2	0
enkephalin-leu, ala(2)-arg(6)- enkephalin-Leu, Ala(2)-Arg(6)-: RN refers to (L-Arg-L-Tyr-D-Ala-L-Phe-L-Leu)-isomer	2.03	1	0
flibanserin [no description available]	2.01	1	0	benzimidazoles; N-alkylpiperazine; N-arylpiperazine; organofluorine compound	antidepressant; serotonergic agonist; serotonergic antagonist
lu 208075 ambrisentan: an ET(A) receptor antagonist and antihypertensive agent; studied for use in pulmonary arterial hypertension	2.74	3	0	diarylmethane
loa lithocholic acid acetate: structure in first source	2.04	1	0
phosphocreatine Phosphocreatine: An endogenous substance found mainly in skeletal muscle of vertebrates. It has been tried in the treatment of cardiac disorders and has been added to cardioplegic solutions. (Reynolds JEF(Ed): Martindale: The Extra Pharmacopoeia (electronic version). Micromedex, Inc, Englewood, CO, 1996). phosphagen : Any of a group of guanidine or amidine phosphates that function as storage depots for high-energy phosphate in muscle with the purpose of regenerating ATP from ADP during muscular contraction.. N-phosphocreatine : A phosphoamino acid consisting of creatine having a phospho group attached at the primary nitrogen of the guanidino group.	1.95	1	0	phosphagen; phosphoamino acid	human metabolite; mouse metabolite
formazans Formazans: Colored azo compounds formed by the reduction of tetrazolium salts. Employing this reaction, oxidoreductase activity can be determined quantitatively in tissue sections by allowing the enzymes to act on their specific substrates in the presence of tetrazolium salts.	2.03	1	0
fosinopril [no description available]	3.15	1	0
s-nitrosocysteine S-nitrosocysteine: A sulfur-containing alkyl thionitrite that is a nitric oxide donor.. S-nitroso-L-cysteine : An L-cysteine derivative in which the sulfur atom carries a nitroso substituent. A cell-permeable low-molecular-weight nitrosothiol and nitric oxide donor.	2.06	1	0	L-cysteine derivative; nitrosothio compound	hematologic agent; platelet aggregation inhibitor; vasodilator agent
ono 8711 ONO 8711: a prostaglandin E receptor EP1 antagonist; structure in first source	2.42	2	0
seryl-leucyl-isoleucyl-glycyl--arginyl-leucinamide seryl-leucyl-isoleucyl-glycyl--arginyl-leucinamide: a proteinase-activated receptor-2-activating peptide; SL-NH2 is NOT Ser-Leu-NH2 here	2.1	1	0
sincalide Sincalide: An octapeptide hormone present in the intestine and brain. When secreted from the gastric mucosa, it stimulates the release of bile from the gallbladder and digestive enzymes from the pancreas.	5.17	15	0	oligopeptide
2164u90 2164U90: a potent inhibitor of the ileal bile acid active transport system; structure given in first source	2.91	4	0
ursodoxicoltaurine tauroursodeoxycholate : An organosulfonate oxoanion that is the conjugate base of tauroursodeoxycholic acid arising from deprotonation of the sulfonate OH group; major species at pH 7.3.. tauroursodeoxycholic acid : A bile acid taurine conjugate derived from ursoodeoxycholic acid.	6.77	79	0	bile acid taurine conjugate	anti-inflammatory agent; apoptosis inhibitor; bone density conservation agent; cardioprotective agent; human metabolite; neuroprotective agent
pentagastrin Pentagastrin: A synthetic pentapeptide that has effects like gastrin when given parenterally. It stimulates the secretion of gastric acid, pepsin, and intrinsic factor, and has been used as a diagnostic aid.	3.34	7	0	organic molecular entity
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).	5.46	59	0	aminopyrimidine; benzamides; pyridines; secondary amino compound; secondary carboxamide; substituted aniline	antineoplastic agent; apoptosis inducer; autophagy inducer; cardioprotective agent; EC 3.5.1.98 (histone deacetylase) inhibitor; hepatotoxic agent
lipid a Lipid A: Lipid A is the biologically active component of lipopolysaccharides. It shows strong endotoxic activity and exhibits immunogenic properties.. lipid A : The glycolipid moiety of bacterial lipopolysaccharide (R can be either hydrogen or a fatty acyl group).	2.31	1	0	dodecanoate ester; lipid A; tetradecanoate ester	Escherichia coli metabolite
gw 4064 [no description available]	3.01	4	0	stilbenoid
lu 302872 LU 224332: endothelin-A/B receptor antagonist	2.42	2	0
g(m2) ganglioside G(M2) Ganglioside: A glycosphingolipid that accumulates due to a deficiency of hexosaminidase A or B (BETA-N-ACETYLHEXOSAMINIDASES), or GM2 activator protein, resulting in GANGLIOSIDOSES, heredity metabolic disorders that include TAY-SACHS DISEASE and SANDHOFF DISEASE.. ganglioside GM2 (18:0) : A sialotriaosylceramide that is N-acetyl-beta-D-galactosaminyl-(1->4)-alpha-N-acetylneuraminosyl-(2->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-N-acylsphingosine in which the acyl group on the sphingosine nitrogen is octadecanoyl. A constituent of natural ganglioside GM2.	3.06	5	0	N-acetyl-beta-D-galactosaminyl-(1->4)-alpha-N-acetylneuraminosyl-(2->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-N-acylsphingosine; sialotriaosylceramide	antigen
gentamicin sulfate [no description available]	2.04	1	0
thiocolchicoside thiocolchicoside: used in combination with glafenine and meprobamate to tranquilize patients undergoing hysterosalpingography; structure	2.01	1	0	glycoside
rhodamine 123 [no description available]	2	1	0	organic chloride salt; xanthene dye	fluorochrome
gw0742 GW 610742: structure in first source	2.07	1	0	monocarboxylic acid
g(m1) ganglioside G(M1) Ganglioside: A specific monosialoganglioside that accumulates abnormally within the nervous system due to a deficiency of GM1-b-galactosidase, resulting in GM1 gangliosidosis.. ganglioside GM1 : A sialotetraosylceramide consisting of a branched pentasaccharide made up from one sialyl residue, two galactose residues, one N-acetylgalactosamine residue and a glucose residue at the reducing end attached to N-stearoylsphingosine via a beta-linkage.	3.21	6	0	alpha-N-acetylneuraminosyl-(2->3)-[beta-D-galactosyl-(1->3)-N-acetyl-beta-D-galactosaminyl-(1->4)]-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1')-N-acylsphingosine; sialotetraosylceramide
diosbulbin b diosbulbin B: from the rhizome of Dioscorea bulbifera; structure in first source	2.06	1	0	naphthofuran
deltorphin ii, ala(2)- [no description available]	2.41	2	0	peptide
fidaxomicin Fidaxomicin: A narrow-spectrum macrolide antibacterial agent that is used in the treatment of diarrhea associated with CLOSTRIDIUM DIFFICILE INFECTION.. fidaxomicin : An 18-membered macrolide that is a fermentation product obtained from the Actinomycete Dactylosporangium aurantiacum. A narrow spectrum antibiotic used for treatment of Clostridium difficile-related infections.	2.08	1	0
betulin-3-caffeate betulin-3-caffeate: has antineoplastic activity; isolated from Hibiscus syriacus; structure in first source	3.51	1	0
heptakis(2,6-o-dimethyl)beta-cyclodextrin heptakis(2,6-O-dimethyl)beta-cyclodextrin: stimulant for Bordetella pertussis Phase I	2.98	4	0
jte 013 JTE 013: an Edg-5 antagonist. JTE-013 : A semicarbazide derivative that is semicarbazide in which the amino group at position 2 is replaced by a [1,3-dimethyl-4-(propan-2-yl)-1H-pyrazolo[3,4-b]pyridin-6-yl]amino group and the amino group adjacent to the carbonyl is replaced by a (2,6-dichloropyridin-4-yl)amino group. It is a potent S1P2 antagonist (IC50 = 17.6 nM).	2.49	2	0	chloropyridine; pyrazolopyridine	anti-asthmatic agent; anti-inflammatory agent; antineoplastic agent; osteogenesis regulator; pro-angiogenic agent; sphingosine-1-phosphate receptor 2 antagonist
troglitazone sulfate troglitazone sulfate: metabolite of troglitazone; structure in first source	2.44	2	0	aromatic ether; thiazolidinone
ko 143 [no description available]	2.46	2	0	beta-carbolines; tert-butyl ester
agosterol a agosterol A: from marine sponge Spongia sp.	2	1	0
aceglutamide aluminum aceglutamide aluminum: structure	1.96	1	0	glutamine derivative
oxadiazoles Oxadiazoles: Compounds containing five-membered heteroaromatic rings containing two carbons, two nitrogens, and one oxygen atom which exist in various regioisomeric forms.	2.91	4	0
ucn 1028 c calphostin C: structure given in first source; isolated from Cladosporium cladosporioides	2.04	1	0
methyl cholate methyl cholate: RN given refers to (3 alpha,5 beta,7 alpha,12 alpha)-isomer	2.03	1	0	bile acid
acebutolol alpha-D-glucosyl-(1->4)-alpha-D-mannose : An alpha-D-glucosyl-(1->4)-D-mannopyranose in which the anomeric hydroxy group has alpha configuration.	2.66	3	0	alpha-D-glucosyl-(1->4)-D-mannopyranose
nystatin a1 Nystatin: Macrolide antifungal antibiotic complex produced by Streptomyces noursei, S. aureus, and other Streptomyces species. The biologically active components of the complex are nystatin A1, A2, and A3.. nystatin : A heterogeneous mixture of polyene compounds produced by cultures of Streptomyces noursei. It mainly consists of three biologically active components designated nystatin A1, nystatin A2, and nystatin A3. It is used to treat oral and dermal fungal infections.. nystatin A1 : A polyene macrolide antibiotic; part of the nystatin complex produced by several Streptomyces species. It is an antifungal antibiotic used for the treatment of topical fungal infections caused by a broad spectrum of fungal pathogens comprising yeast-like and filamentous species.	2.78	3	0	nystatins
technetium tc 99m disofenin Technetium Tc 99m Disofenin: A radiopharmaceutical used extensively in cholescintigraphy for the evaluation of hepatobiliary diseases. (From Int Jrnl Rad Appl Inst 1992;43(9):1061-4)	1.96	1	0
losartan potassium Erythropoietin: Glycoprotein hormone, secreted chiefly by the KIDNEY in the adult and the LIVER in the FETUS, that acts on erythroid stem cells of the BONE MARROW to stimulate proliferation and differentiation.	2.69	3	0
calcimycin Calcimycin: An ionophorous, polyether antibiotic from Streptomyces chartreusensis. It binds and transports CALCIUM and other divalent cations across membranes and uncouples oxidative phosphorylation while inhibiting ATPase of rat liver mitochondria. The substance is used mostly as a biochemical tool to study the role of divalent cations in various biological systems.	3.08	5	0	benzoxazole
sepharose agarose : A linear polysaccharide made up from alternating D-galactose and 3,6-anhydro-alpha-L-galactopyranose residues joined by alpha-(1->3)- and beta-(1->4)-linkages.	3.78	3	0
indocyanine green Indocyanine Green: A tricarbocyanine dye that is used diagnostically in liver function tests and to determine blood volume and cardiac output.	4.45	23	0	1,1-diunsubstituted alkanesulfonate; benzoindole; cyanine dye
scopolamine hydrobromide [no description available]	2.06	1	0
pituitrin Pituitrin: A substance or extract from the neurohypophysis (PITUITARY GLAND, POSTERIOR).	4.05	15	0
phytosterols Phytosterols: A class of organic compounds known as sterols or STEROIDS derived from plants.. phytosterols : Sterols similar to cholesterol which occur in plants and vary only in carbon side chains and/or presence or absence of a double bond.	2.92	4	0
glycoursodeoxycholic acid glycoursodeoxycholic acid : A bile acid glycine conjugate derived from ursoodeoxycholic acid.. glycoursodeoxycholate : A N-acylglycinate that is the conjugate base of glycoursodeoxycholic acid. obtained by deprotonation of the carboxy group; major species at pH 7.3.	3.94	13	0	bile acid glycine conjugate; N-acylglycine	human blood serum metabolite; neuroprotective agent
dihydrotachysterol Dihydrotachysterol: A VITAMIN D that can be regarded as a reduction product of vitamin D2.. dihydrotachysterol : A hydroxy seco-steroid that is 9,10-secoergosta-5,7,22-triene substituted by a hydroxy group at position 3. A synthetic analogue of vitamin D that acts a bone density conservation agent.	1.94	1	0
rifamycins [no description available]	3.09	5	0
taurodehydrocholate taurodehydrocholate: RN given refers to parent cpd	4.37	21	0
vpm chloride VPM chloride: structure given in first source	2.21	1	0
acid phosphatase Acid Phosphatase: An enzyme that catalyzes the conversion of an orthophosphoric monoester and water to an alcohol and orthophosphate. EC 3.1.3.2.	3.46	8	0
2',7'-dichlorodihydrofluorescein 2',7'-dichlorodihydrofluorescein: nonfluorescent, reduced form of 2',7'-dichlorofluorescein	2	1	0
icatibant icatibant: a potent bradykinin (B2) receptor antagonist; WIN 65365 is an L-Tic(7) stereoisomer. icatibant : A ten-membered synthetic oligopeptide consisting of D-Arg, Arg, Pro, Hyp, Gly, Thi, Ser, D-Tic, Oic, and Arg residues joined in sequrence. A bradykinin receptor antagonist used as its acetate salt for the treatment of acute attacks of hereditary angioedema in adult patients.	2.68	3	0
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	2.88	4	0	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
macitentan [no description available]	2.1	1	0	aromatic ether; organobromine compound; pyrimidines; ring assembly; sulfamides	antihypertensive agent; endothelin receptor antagonist; orphan drug
amodiaquine hydrochloride [no description available]	2.46	2	0
calcitonin [no description available]	2.43	2	0
cosyntropin Cosyntropin: A synthetic peptide that is identical to the 24-amino acid segment at the N-terminal of ADRENOCORTICOTROPIC HORMONE. ACTH (1-24), a segment similar in all species, contains the biological activity that stimulates production of CORTICOSTEROIDS in the ADRENAL CORTEX.. cosyntropin : A synthetic peptide that is identical to the 24-amino acid segment at the N-terminal of adrenocorticotropic hormone (corticotropin). A segment similar in all species, it contains the biological activity that stimulates production of corticosteroids in the adrenal cortex. It is used diagnostically to investigate adrenocortical insufficiency.	2.04	1	0
cholecystokinin Cholecystokinin: A peptide, of about 33 amino acids, secreted by the upper INTESTINAL MUCOSA and also found in the central nervous system. It causes gallbladder contraction, release of pancreatic exocrine (or digestive) enzymes, and affects other gastrointestinal functions. Cholecystokinin may be the mediator of satiety.	6.41	33	0
ceruletide Ceruletide: A specific decapeptide obtained from the skin of Hila caerulea, an Australian amphibian. Caerulein is similar in action and composition to CHOLECYSTOKININ. It stimulates gastric, biliary, and pancreatic secretion; and certain smooth muscle. It is used in paralytic ileus and as diagnostic aid in pancreatic malfunction.. ceruletide : A decapeptide comprising 5-oxoprolyl, glutamyl, aspartyl, O-sulfotyrosyl, threonyl, glycyl, tryptopyl, methionyl, aspartyl and phenylalaninamide residues in sequence. Found in the skins of certain Australian amphibians, it is an analogue of the gastrointestinal peptide hormone cholecystokinin and stimulates gastric, biliary, and pancreatic secretion. It is used in cases of paralysis of the intestine (paralytic ileus) and as a diagnostic aid in pancreatic malfunction.	7.55	67	0	oligopeptide	diagnostic agent; gastrointestinal drug
motilin Motilin: A peptide of about 22-amino acids isolated from the DUODENUM. At low pH it inhibits gastric motor activity, whereas at high pH it has a stimulating effect.	1.97	1	0
thymalfasin Thymalfasin: A thymus hormone polypeptide found in thymosin fraction 5 (a crude thymus gland extract) but now produced by synthesis. It is used alone or with interferon as an immunomodulator for the treatment of CHRONIC HEPATITIS B and HEPATITIS C. Thymalfasin is also used for the treatment of chemotherapy-induced immunosuppression, and to enhance the efficacy of influenza and hepatitis B vaccines in immunocompromised patients.	2.03	1	0	polypeptide
adrenocorticotropin zinc [no description available]	2.04	1	0
gastrins Gastrins: A family of gastrointestinal peptide hormones that excite the secretion of GASTRIC JUICE. They may also occur in the central nervous system where they are presumed to be neurotransmitters.	3.67	10	0
gramicidin a Gramicidin: A group of peptide antibiotics from BACILLUS brevis. Gramicidin C or S is a cyclic, ten-amino acid polypeptide and gramicidins A, B, D are linear. Gramicidin is one of the two principal components of TYROTHRICIN.	1.97	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.	10.99	27	1	peptide hormone
beta-endorphin beta-Endorphin: A 31-amino acid peptide that is the C-terminal fragment of BETA-LIPOTROPIN. It acts on OPIOID RECEPTORS and is an analgesic. Its first four amino acids at the N-terminal are identical to the tetrapeptide sequence of METHIONINE ENKEPHALIN and LEUCINE ENKEPHALIN.. beta-endorphin : A polypeptide consisting of 31 amino acid residues in the sequence Tyr-Gly-Gly-Phe-Met-Thr-Ser-Glu-Lys-Ser-Gln-Thr-Pro-Leu-Val-Thr-Leu-Phe-Lys-Asn-Ala-Ile-Ile-Lys-Asn-Ala-Tyr-Lys-Lys-Gly-Glu. It is an endogenous opioid peptide neurotransmitter found in the neurons of both the central and peripheral nervous system and results from processing of the precursor protein proopiomelanocortin (POMC).	1.96	1	0
cyn 154806 [no description available]	2.05	1	0
oligonucleotides [no description available]	2.13	1	0
glucagon-like peptide 1 Glucagon-Like Peptide 1: A peptide of 36 or 37 amino acids that is derived from PROGLUCAGON and mainly produced by the INTESTINAL L CELLS. GLP-1(1-37 or 1-36) is further N-terminally truncated resulting in GLP-1(7-37) or GLP-1-(7-36) which can be amidated. These GLP-1 peptides are known to enhance glucose-dependent INSULIN release, suppress GLUCAGON release and gastric emptying, lower BLOOD GLUCOSE, and reduce food intake.	4.71	6	1
c-peptide C-Peptide: The middle segment of proinsulin that is between the N-terminal B-chain and the C-terminal A-chain. It is a pancreatic peptide of about 31 residues, depending on the species. Upon proteolytic cleavage of proinsulin, equimolar INSULIN and C-peptide are released. C-peptide immunoassay has been used to assess pancreatic beta cell function in diabetic patients with circulating insulin antibodies or exogenous insulin. Half-life of C-peptide is 30 min, almost 8 times that of insulin.	3.86	2	1
cellulose DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.	5.79	12	2	glycoside
endothelin-1 Endothelin-1: A 21-amino acid peptide produced in a variety of tissues including endothelial and vascular smooth-muscle cells, neurons and astrocytes in the central nervous system, and endometrial cells. It acts as a modulator of vasomotor tone, cell proliferation, and hormone production. (N Eng J Med 1995;333(6):356-63)	2.94	4	0
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	9.74	157	1	1,2-diacyl-sn-glycero-3-phosphocholine
n-(7-(4-nitrobenzo-2-oxa-1,3-diazole))-6-aminocaproyl sphingosine N-(7-(4-nitrobenzo-2-oxa-1,3-diazole))-6-aminocaproyl sphingosine: fluorescent ceramide analog; structure given in first source. N-{6-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]hexanoyl}sphingosine : An N-acylsphingosine that is sphingosine with the amino nitrogen converted into a 6-{[N-(7-nitrobenzo-2,1,3-oxadiazol-4-yl)amino]}hexananamido group.	1.97	1	0	N-acylsphingosine	fluorescent probe
chlorophyll a Chlorophyll: Porphyrin derivatives containing magnesium that act to convert light energy in photosynthetic organisms.. chlorophyll : A family of magnesium porphyrins, defined by the presence of a fifth ring beyond the four pyrrole-like rings. The rings can have various side chains which usually include a long phytol chain.	2.87	4	0	chlorophyll; methyl ester	cofactor
sodium salicylate [no description available]	2.65	3	0	organic molecular entity
ubiquinone Ubiquinone: A lipid-soluble benzoquinone which is involved in ELECTRON TRANSPORT in mitochondrial preparations. The compound occurs in the majority of aerobic organisms, from bacteria to higher plants and animals.	3.77	2	1
n-(2-methylbenzyl)linoleamide N-(2-methylbenzyl)linoleamide: RN given refers to (Z,Z)-isomer; structure	1.96	1	0	organic molecular entity
k-strophanthoside K-strophanthoside: cardiac glycoside extracted from Strophanthus kombe; sugars (glucose-glucose-cymarose) are bonded with strophanthidin	2	1	0
glycochenodeoxycholate-3-sulfate sulfoglycochenodeoxycholic acid : A steroid sulfate that is the 3-O-sulfo derivative of glycochenodeoxycholic acid.	2.41	2	0	7alpha-hydroxy steroid; bile acid glycine conjugate; steroid sulfate	metabolite
antamanide antamanide: cyclic decapeptides otained from the green death cup toadstool (Amanita phalloides). Acts as an antidote against poisoning by phallotoxins by preventing accumulation & absorption of the toxin in the liver; minor descriptor (75-86); on-line & INDEX MEDICUS search PEPTIDES, CYCLIC (75-86)	1.96	1	0
chitosan [no description available]	3.16	5	0
technetium tc 99m sestamibi Technetium Tc 99m Sestamibi: A technetium imaging agent used to reveal blood-starved cardiac tissue during a heart attack.	2.03	1	0
cholylglycylamidofluorescein [no description available]	2.03	1	0
meglumine ioxithalamate meglumine ioxithalamate: structure	2.03	1	0
bucladesine Bucladesine: A cyclic nucleotide derivative that mimics the action of endogenous CYCLIC AMP and is capable of permeating the cell membrane. It has vasodilator properties and is used as a cardiac stimulant. (From Merck Index, 11th ed). bucladesine : A 3',5'-cyclic purine nucleotide that is the 2'-butanoate ester and 6-N-butanoyl derivative of 3',5'-cyclic AMP.	4.18	17	0	3',5'-cyclic purine nucleotide
osteum [no description available]	2.11	1	0	organic molecular entity
sodium hypochlorite Sodium Hypochlorite: It is used as an oxidizing and bleaching agent and as a disinfectant. (From Grant & Hackh's Chemical Dictionary, 5th ed). sodium hypochlorite : An inorganic sodium salt in which hypochlorite is the counterion. It is used as a bleaching and disinfecting agent and is commonly found in household bleach.	2.9	4	0	inorganic sodium salt	bleaching agent; disinfectant
taurocholic acid, monosodium salt [no description available]	3.15	1	0	bile salt
(7,7-azo-3,12-dihydroxy-5-cholan-24-oyl)-2-aminoethanesulfonic acid (7,7-azo-3,12-dihydroxy-5-cholan-24-oyl)-2-aminoethanesulfonic acid: photolabile bile acid derivative	3.22	6	0
pd 180988 PD 180988: endothelin-A-receptor antagonist	2.01	1	0
ro13-9904 Ceftriaxone: A broad-spectrum cephalosporin antibiotic and cefotaxime derivative with a very long half-life and high penetrability to meninges, eyes and inner ears.. ceftriaxone : A third-generation cephalosporin compound having 2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetylamino and [(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl side-groups.	2.38	2	0
(2-sulfonatoethyl)methanethiosulfonate (2-sulfonatoethyl)methanethiosulfonate: RN given for Na salt	2	1	0
sodium scymnol sulfate scymnol sulfate ester: from gall bladder of Rhizoprionodon acutus; structure given in first source	2.41	2	0
mersalyl Mersalyl: A toxic thiol mercury salt formerly used as a diuretic. It inhibits various biochemical functions, especially in mitochondria, and is used to study those functions.	2.36	2	0
phenolphthalein glucuronide phenolphthalein glucuronide: RN given refers to parent cpd	2.02	1	0
srt1720 [no description available]	2.17	1	0
s-adenosylmethionine (R)-S-adenosyl-L-methionine : An S-adenosyl-L-methionine that has R-configuration.. S-adenosyl-L-methionine zwitterion : A zwitterionic tautomer of S-adenosyl-L-methionine arising from shift of the proton from the carboxy group to the amino group.. (R)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has R-configuration; major species at pH 7.3.. (S)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has S-configuration; major species at pH 7.3.. S-adenosyl-L-methionine : A sulfonium compound that is the S-adenosyl derivative of L-methionine. It is an intermediate in the metabolic pathway of methionine.	2.36	2	0	organic cation; sulfonium compound	coenzyme; cofactor; human metabolite; micronutrient; Mycoplasma genitalium metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
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.	2.11	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
intrinsic factor Intrinsic Factor: A glycoprotein secreted by the cells of the GASTRIC GLANDS that is required for the absorption of VITAMIN B 12 (cyanocobalamin). Deficiency of intrinsic factor leads to VITAMIN B 12 DEFICIENCY and ANEMIA, PERNICIOUS.	2.89	4	0
tak-875 [no description available]	3.51	1	0	biphenyls
cardiovascular agents Cardiovascular Agents: Agents that affect the rate or intensity of cardiac contraction, blood vessel diameter, or blood volume.	2.43	2	0
neurotensin neurotensin, Tyr(11)-: RN given refers to parent cpd & (D)-isomer; RN for cpd without isomeric designation not avail 5/91	8.51	8	0	peptide hormone	human metabolite; mitogen; neurotransmitter; vulnerary
mannans [no description available]	2.68	3	0
taurolithocholic acid 3-sulfate taurolithocholic acid sulfate(2-) : A steroid sulfate oxoanion arising from deprotonation of both sulfo groups of taurolithocholic acid sulfate; major species at pH 7.3.	3.11	5	0	steroid sulfate oxoanion	human metabolite
peptones Peptones: Derived proteins or mixtures of cleavage products produced by the partial hydrolysis of a native protein either by an acid or by an enzyme. Peptones are readily soluble in water, and are not precipitable by heat, by alkalis, or by saturation with ammonium sulfate. (Dorland, 28th ed)	1.95	1	0
phallacidin phallacidin: bicyclic heptapeptide from Amanita (along with phalloidin). phallacidin : A homodetic bicyclic heptapeptide having a sulfide bridge.	1.96	1	0	homodetic cyclic peptide
glycolipids [no description available]	4.32	20	0
piperidines Piperidines: A family of hexahydropyridines.	3.52	8	0
dihydrotestosterone glucuronide dihydrotestosterone glucuronide: RN given refers to (5alpha,17beta)-isomer. 5alpha-dihydrotestosterone 17-O-(beta-D-glucuronide) : A steroid glucosiduronic acid that is 5alpha-dihydrotestosterone having a single beta-D-glucuronic acid residue attached at position 17.	1.96	1	0	3-oxo-5alpha-steroid; steroid glucosiduronic acid	human urinary metabolite
endothelins [no description available]	2	1	0
thymosin Thymosin: Thymosin. A family of heat-stable, polypeptide hormones secreted by the thymus gland. Their biological activities include lymphocytopoiesis, restoration of immunological competence and enhancement of expression of T-cell characteristics and function. They have therapeutic potential in patients having primary or secondary immunodeficiency diseases, cancer or diseases related to aging.	2.03	1	0
galactocerebroside galactocerebroside: a NITROGEN containing sphingolipid	1.98	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.	2.72	3	0
colistin Colistin: Cyclic polypeptide antibiotic from Bacillus colistinus. It is composed of Polymyxins E1 and E2 (or Colistins A, B, and C) which act as detergents on cell membranes. Colistin is less toxic than Polymyxin B, but otherwise similar; the methanesulfonate is used orally.. colistin : A multi-component mixture comprising mostly of colistin A (R = Me) and B (R = H), with small amounts of colistin C and other polymyxins, produced by certain strains of Bacillus polymyxa var. colistinus. An antibiotic, it is used as its sulfate salt (for oral or topical use) or as the sodium salt of the N-methylsulfonic acid derivative (the injectable form) in the treatment of severe Gram-negative infections, partiularly those due to Pseudomonas aeruginosa.	2.41	1	0
sofosbuvir Sofosbuvir: A uridine monophosphate analog inhibitor of HEPATITIS C VIRUS (HCV) polymerase NS5B that is used as an ANTIVIRAL AGENT in the treatment of CHRONIC HEPATITIS C.. sofosbuvir : A nucleotide conjugate that is used in combination with ledipasvir (under the trade name Harvoni) for the treatment of chronic hepatitis C genotype 1 infection.	2.25	1	0	isopropyl ester; L-alanyl ester; nucleotide conjugate; organofluorine compound; phosphoramidate ester	antiviral drug; hepatitis C protease inhibitor; prodrug
int-777 [no description available]	2.52	2	0
exenatide Exenatide: A synthetic form of exendin-4, a 39-amino acid peptide isolated from the venom of the Gila monster lizard (Heloderma suspectum). Exenatide increases CYCLIC AMP levels in pancreatic acinar cells and acts as a GLUCAGON-LIKE PEPTIDE-1 RECEPTOR (GLP-1) agonist and incretin mimetic, enhancing insulin secretion in response to increased glucose levels; it also suppresses inappropriate glucagon secretion and slows gastric emptying. It is used an anti-diabetic and anti-obesity agent.	2.25	1	0
methylcellulose Methylcellulose: Methylester of cellulose. Methylcellulose is used as an emulsifying and suspending agent in cosmetics, pharmaceutics and the chemical industry. It is used therapeutically as a bulk laxative.	2.48	2	0
oligomycin a [no description available]	1.99	1	0	antibiotic antifungal agent; diketone; oligomycin; pentol	antineoplastic agent; EC 3.6.3.14 (H(+)-transporting two-sector ATPase) inhibitor; nematicide
vasoactive intestinal peptide Vasoactive Intestinal Peptide: A highly basic, 28 amino acid neuropeptide released from intestinal mucosa. It has a wide range of biological actions affecting the cardiovascular, gastrointestinal, and respiratory systems and is neuroprotective. It binds special receptors (RECEPTORS, VASOACTIVE INTESTINAL PEPTIDE).	3.48	8	0
heme Heme: The color-furnishing portion of hemoglobin. It is found free in tissues and as the prosthetic group in many hemeproteins.. ferroheme : Any iron(II)--porphyrin coordination complex.. ferroheme b : Heme b in which the iron has oxidation state +2.. heme : A heme is any tetrapyrrolic chelate of iron.	2.11	1	0
heparitin sulfate Heparitin Sulfate: A heteropolysaccharide that is similar in structure to HEPARIN. It accumulates in individuals with MUCOPOLYSACCHARIDOSIS.	2.11	1	0
tuftsin Tuftsin: N(2)-((1-(N(2)-L-Threonyl)-L-lysyl)-L-prolyl)-L-arginine. A tetrapeptide produced in the spleen by enzymatic cleavage of a leukophilic gamma-globulin. It stimulates the phagocytic activity of blood polymorphonuclear leukocytes and neutrophils in particular. The peptide is located in the Fd fragment of the gamma-globulin molecule.	2.41	1	0	peptide
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	2.89	4	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.	4.25	5	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.	3.53	8	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.	3.46	8	0	monohydroxybenzoate	plant metabolite
piroxicam [no description available]	2.95	4	0	benzothiazine; monocarboxylic acid amide; pyridines	analgesic; antirheumatic drug; cyclooxygenase 1 inhibitor; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-steroidal anti-inflammatory drug
mobic Meloxicam: A benzothiazine and thiazole derivative that acts as a NSAID and cyclooxygenase-2 (COX-2) inhibitor. It is used in the treatment of RHEUMATOID ARTHRITIS; OSTEOARTHRITIS; and ANKYLOSING SPONDYLITIS.. meloxicam : A benzothiazine that is piroxicam in which the pyridin-2-yl group is replaced by a 5-methyl-1,3-thiazol-2-yl group. A non-steroidal anti-inflammatory drug and selective inhibitor of COX-2, it is used particularly for the management of rheumatoid arthritis.	2.06	1	0	1,3-thiazoles; benzothiazine; monocarboxylic acid amide	analgesic; antirheumatic drug; cyclooxygenase 2 inhibitor; non-steroidal anti-inflammatory drug
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.	4.8	10	0	benzenes; hydroxycoumarin; methyl ketone
tipranavir tipranavir: inhibits HIV-1 protease. tipranavir : A pyridine-2-sulfonamide substituted at C-5 by a trifluoromethyl group and at the sulfonamide nitrogen by a dihydropyrone-containing m-tolyl substituent. It is an HIV-1 protease inhibitor.	2.46	2	0	sulfonamide	antiviral drug; HIV protease inhibitor
potassium ascorbyl tocopheryl phosphate potassium ascorbyl tocopheryl phosphate: RN given refers to the potassium salt	2	1	0
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.	1.98	1	0
microcystin microcystin: microcystins have the general structure cyclo(D-Ala-L-X-D-erythro--methylisoasp-L-Y-Adda-D-isoGlu-N-methyldehydroAla) where X and Y are variable L-amino acids;. microcystin : A family of cyclic heptapeptide hepatotoxins produced by a number of cyanobacteria, the most notable of which is Microcystis, from which the name of the family is derived. Microcystins consist of a heptapeptide macrocycle made up of five non-protein amino acids and two protein amino acids.	1.98	1	0	peptide
calca protein, human CALCA protein, human: RefSeq NM_001741	2.15	1	0
vasoactive intestinal peptide, 4-chloro-phe(6)-leu(17)- vasoactive intestinal peptide, 4-chloro-Phe(6)-Leu(17)-: VIP receptor antagonist	2.02	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.	2.01	1	0
pyrethrins [no description available]	2.07	1	0
3-(6-isobutyl-9-methoxy-1,4-dioxo-1,2,3,4,6,7,12,12a-octahydropyrazino(1',2'-1,6)pyrido(3,4-b)indol-3-yl)propionic acid tert-butyl ester 3-(6-isobutyl-9-methoxy-1,4-dioxo-1,2,3,4,6,7,12,12a-octahydropyrazino(1',2'-1,6)pyrido(3,4-b)indol-3-yl)propionic acid tert-butyl ester: a breast cancer resistance protein (BCRP) inhibitor; structure in first source	2.31	1	0
fti 277 FTI 277: a ras CAAX (C - Cys; A - aliphatic amino acid; X - Ser or Met) peptidomimetic; inhibits farnesyltransferase; blocks Ras oncogenic signaling by accumulating Ras/Raf complexes in the cytoplasm; structure given in first source	2.1	1	0
agar Agar: A complex sulfated polymer of galactose units, extracted from Gelidium cartilagineum, Gracilaria confervoides, and related red algae. It is used as a gel in the preparation of solid culture media for microorganisms, as a bulk laxative, in making emulsions, and as a supporting medium for immunodiffusion and immunoelectrophoresis.. agar : A complex mixture of polysaccharides extracted from species of red algae. Its two main components are agarose and agaropectin. Agarose is the component responsible for the high-strength gelling properties of agar, while agaropectin provides the viscous properties.	3.24	6	0
technetium tc 99m lidofenin Technetium Tc 99m Lidofenin: A nontoxic radiopharmaceutical that is used in RADIONUCLIDE IMAGING for the clinical evaluation of hepatobiliary disorders in humans.	2.38	2	0
sorbitan monolaurate sorbitan monolaurate: span type materials are artificial esters of the common fatty acids & hexitol anhydrides derived from sorbitol	2.05	1	0
caseins Caseins: A mixture of related phosphoproteins occurring in milk and cheese. The group is characterized as one of the most nutritive milk proteins, containing all of the common amino acids and rich in the essential ones.	5.43	15	0
penimocycline penimocycline: obtained by Mannich reaction between tetracycline & ampicillin; structure	2.21	1	0
sdz co 611 SDZ CO 611: structure given in first source; an Amadori compound of octreotide	1.98	1	0
oligomycins Oligomycins: A closely related group of toxic substances elaborated by various strains of Streptomyces. They are 26-membered macrolides with lactone moieties and double bonds and inhibit various ATPases, causing uncoupling of phosphorylation from mitochondrial respiration. Used as tools in cytochemistry. Some specific oligomycins are RUTAMYCIN, peliomycin, and botrycidin (formerly venturicidin X).	1.98	1	0
g(m3) ganglioside G(M3) Ganglioside: A ganglioside present in abnormally large amounts in the brain and liver due to a deficient biosynthetic enzyme, G(M3):UDP-N-acetylgalactosaminyltransferase. Deficiency of this enzyme prevents the formation of G(M2) ganglioside from G(M3) ganglioside and is the cause of an anabolic sphingolipidosis.. alpha-Neu5Ac-(2->3)-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1')-Cer(d18:1/24:1(15Z)) : A sialotriaosylceramide consisting of beta-D-GalNAc-(1->4)-[alpha-Neu5Ac-(2->3)]-beta-D-Gal-(1->4)-beta-D-Glc attached to the primary hydroxy function of ceramide(d18:1/24:1(15Z)).	1.96	1	0	alpha-N-acetylneuraminyl-(2->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1')-ceramide; sialodiosylceramide; sialotriaosylceramide	mouse metabolite
benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone: an interleukin-1beta converting enzyme (ICE)-like protease inhibitor	2.03	1	0
nitrophenols Nitrophenols: PHENOLS carrying nitro group substituents.	3.35	7	0
bassianolide bassianolide: cyclodepsipeptide from mycelia of Beauveria bassiana; inhibits isotonic contractions induced by acetylcholine. bassianolide : A cyclodepsipeptide consisting of a cyclic tetramer of the depsipeptide D-Hiv-N-methyl-L-leucine (where D-Hiv = D-alpha-hydroxyisovaleric acid). Found in the fungal species Beauveria bassiana and Verticillium lecanii, it has insecticidal properties and is used as a commercial biopesticide to control of insects of agricultural, veterinary and medical significance. For elucidation of the structure, see Suzuki et al., Tetrahedron Lett. 1977 v25, 2167-2170.	2.41	1	0	cyclodepsipeptide; cyclooctadepsipeptide	antineoplastic agent; fungal metabolite; insecticide
gadoxetic acid disodium gadolinium ethoxybenzyl DTPA: DTPA covalently linked to the lipoohilic ethoxybenzyl moiety; a contrast agent in MR imaging of hepatobiliary system	2.7	3	0
ginkgolide b [no description available]	3.08	5	0
vitamin b 12 Vitamin B 12: A cobalt-containing coordination compound produced by intestinal micro-organisms and found also in soil and water. Higher plants do not concentrate vitamin B 12 from the soil and so are a poor source of the substance as compared with animal tissues. INTRINSIC FACTOR is important for the assimilation of vitamin B 12.	3.67	10	0
oxyntomodulin Glucagon-Like Peptides: Peptides derived from proglucagon which is also the precursor of pancreatic GLUCAGON. Despite expression of proglucagon in multiple tissues, the major production site of glucagon-like peptides (GLPs) is the INTESTINAL L CELLS. GLPs include glucagon-like peptide 1, glucagon-like peptide 2, and the various truncated forms.	2.01	1	0
cyclosporine Cyclosporine: A cyclic undecapeptide from an extract of soil fungi. It is a powerful immunosupressant with a specific action on T-lymphocytes. It is used for the prophylaxis of graft rejection in organ and tissue transplantation. (From Martindale, The Extra Pharmacopoeia, 30th ed).	4.59	25	0
alpha1-purothionin protein, wheat purothionin: polypeptide of relatively low MW; toxic to vertebrates and some bacteria & yeasts; purothionin A-I is believed to be identical to beta-purothionin; RN given refers to cpd with unknown MF	1.99	1	0
silybin Silybin: The major active component of silymarin flavonoids extracted from seeds of the MILK THISTLE, Silybum marianum; it is used in the treatment of HEPATITIS; LIVER CIRRHOSIS; and CHEMICAL AND DRUG INDUCED LIVER INJURY, and has antineoplastic activity; silybins A and B are diastereomers.	2.4	2	0
cytochalasin d Cytochalasin D: A fungal metabolite that blocks cytoplasmic cleavage by blocking formation of contractile microfilament structures resulting in multinucleated cell formation, reversible inhibition of cell movement, and the induction of cellular extrusion. Additional reported effects include the inhibition of actin polymerization, DNA synthesis, sperm motility, glucose transport, thyroid secretion, and growth hormone release.. cytochalasin D : An organic heterotricyclic compound that is a mycotoxin produced by Helminthosporium and other moulds which is cell permeable and a potent inhibitor of actin polymerisation and DNA synthesis.	2.9	4	0
op-1118 OP-1118: antibacterial major metabolite of fidaxomicin	2.08	1	0
peptide yy Peptide YY: A 36-amino acid peptide produced by the L cells of the distal small intestine and colon. Peptide YY inhibits gastric and pancreatic secretion.. peptide YY : A 36-membered human gut polypeptide consisting of Tyr, Pro, Ile, Lys, Pro, Glu, Ala, Pro, Gly, Glu, Asp, Ala, Ser, Pro, Glu, Glu, Leu, Asn, Arg, Tyr, Tyr, Ala, Ser, Leu, Arg, His, Tyr, Leu, Asn, Leu, Val, Thr, Arg, Gln, Arg and Tyr-NH2 residues joined in sequence.	8.26	6	0
lactoferrin Lactoferrin: An iron-binding protein that was originally characterized as a milk protein. It is widely distributed in secretory fluids and is found in the neutrophilic granules of LEUKOCYTES. The N-terminal part of lactoferrin possesses a serine protease which functions to inactivate the TYPE III SECRETION SYSTEM used by bacteria to export virulence proteins for host cell invasion.	2.15	1	0
digitonin Digitonin: A glycoside obtained from Digitalis purpurea; the aglycone is digitogenin which is bound to five sugars. Digitonin solubilizes lipids, especially in membranes and is used as a tool in cellular biochemistry, and reagent for precipitating cholesterol. It has no cardiac effects.. digitonin : A spirostanyl glycoside that is digitogenin in which the 3-hydroxy group is substituted by a beta-D-glucopyranosyl-(1->3)-beta-D-galactopyranosyl-(1->2)-[beta-D-xylopyranosyl-(1->3)]-beta-D-glucopyranosyl-(1->4)-beta-D-galactopyranosyl group. It is a steroidal saponin isolated from the foxglove plant, Digitalis purpurea. It is used extensively as a mild non-ionic detergent for extracting proteins from membranes for structure and function studies.	3.05	5	0
catalpol catalpol: component of dihuang; RN given refers to (1aS-(1aalpha,1bbeta,2beta,5abeta,6beta,6aalpha))-isomer; RN for cpd without isomeric designation not avail 12/92	2.1	1	0
orabase Orabase: used in therapy of oral mucosal ulcers	2.08	1	0
thromboplastin Thromboplastin: Constituent composed of protein and phospholipid that is widely distributed in many tissues. It serves as a cofactor with factor VIIa to activate factor X in the extrinsic pathway of blood coagulation.	1.95	1	0
muramidase Muramidase: A basic enzyme that is present in saliva, tears, egg white, and many animal fluids. It functions as an antibacterial agent. The enzyme catalyzes the hydrolysis of 1,4-beta-linkages between N-acetylmuramic acid and N-acetyl-D-glucosamine residues in peptidoglycan and between N-acetyl-D-glucosamine residues in chitodextrin. EC 3.2.1.17.	4.76	7	1
amyloid beta-peptides amyloid beta-protein (1-40): although acutely neurotoxic in both rat & monkey cerebral cortex, neuronal degeneration in primates resembles more closely to that found in Alzheimer's disease; amino acid sequence has been determined	2.31	1	0
chondroitin sulfates Chondroitin Sulfates: Derivatives of chondroitin which have a sulfate moiety esterified to the galactosamine moiety of chondroitin. Chondroitin sulfate A, or chondroitin 4-sulfate, and chondroitin sulfate C, or chondroitin 6-sulfate, have the sulfate esterified in the 4- and 6-positions, respectively. Chondroitin sulfate B (beta heparin; DERMATAN SULFATE) is a misnomer and this compound is not a true chondroitin sulfate.	2.31	1	0
prajmaline Prajmaline: A derivative of the rauwolfia alkaloid AJMALINE. It is an anti-arrhythmia agent but may cause liver damage.	1.97	1	0
acyclovir Acyclovir: A GUANOSINE analog that acts as an antimetabolite. Viruses are especially susceptible. Used especially against herpes.. acyclovir : An oxopurine that is guanine substituted by a (2-hydroxyethoxy)methyl substituent at position 9. Used in the treatment of viral infections.	4.22	5	0	2-aminopurines; oxopurine	antimetabolite; antiviral drug
levoleucovorin Levoleucovorin: A folate analog consisting of the pharmacologically active isomer of LEUCOVORIN.. (6S)-5-formyltetrahydrofolic acid : The pharmacologically active (6S)-stereoisomer of 5-formyltetrahydrofolic acid.	2.01	1	0	5-formyltetrahydrofolic acid	antineoplastic agent; metabolite
5-methyltetrahydrofolate (6S)-5-methyltetrahydrofolic acid : A 5-methyltetrahydrofolic acid that has 6S-configuration.	2	1	0	5-methyltetrahydrofolic acid
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.	4.49	7	0	3',5'-cyclic purine nucleotide; guanyl ribonucleotide	Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
deoxyguanosine [no description available]	2.43	2	0	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
guanosine diphosphate mannose Guanosine Diphosphate Mannose: A nucleoside diphosphate sugar which can be converted to the deoxy sugar GDPfucose, which provides fucose for lipopolysaccharides of bacterial cell walls. Also acts as mannose donor for glycolipid synthesis.. GDP-D-mannose : A GDP-mannose in which the mannose fragment has D-configuration.. GDP-alpha-D-mannose : The alpha-anomer of GDP-D-mannose.	2.36	2	0	GDP-D-mannose	Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite
guanosine monophosphate Guanosine Monophosphate: A guanine nucleotide containing one phosphate group esterified to the sugar moiety and found widely in nature.. guanosine 5'-monophosphate : A purine ribonucleoside 5'-monophosphate having guanine as the nucleobase.	1.95	1	0	guanosine 5'-phosphate; purine ribonucleoside 5'-monophosphate	biomarker; Escherichia coli metabolite; metabolite; mouse metabolite
inosine [no description available]	1.99	1	0	inosines; purines D-ribonucleoside	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.	3.26	6	0	folic acids; N-acyl-amino acid	human metabolite; mouse metabolite; nutrient
3-methyladenine N3-methyladenine: structure in first source	2.13	1	0
guanosine 5'-o-(3-thiotriphosphate) Guanosine 5'-O-(3-Thiotriphosphate): Guanosine 5'-(trihydrogen diphosphate), monoanhydride with phosphorothioic acid. A stable GTP analog which enjoys a variety of physiological actions such as stimulation of guanine nucleotide-binding proteins, phosphoinositide hydrolysis, cyclic AMP accumulation, and activation of specific proto-oncogenes.	2.39	2	0	nucleoside triphosphate analogue
neopterin [no description available]	2.05	1	0
rifampin Rifampin: A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)	5.49	20	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
ganciclovir [no description available]	2.06	1	0	2-aminopurines; oxopurine	antiinfective agent; antiviral drug
valacyclovir Valacyclovir: A prodrug of acyclovir that is used in the treatment of HERPES ZOSTER and HERPES SIMPLEX VIRUS INFECTION of the skin and mucous membranes, including GENITAL HERPES.	4.07	4	0	L-valyl ester	antiviral drug
sildenafil sildenafil : A pyrazolo[4,3-d]pyrimidin-7-one having a methyl substituent at the 1-position, a propyl substituent at the 3-position and a 2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl group at the 5-position.	2.95	4	0	piperazines; pyrazolopyrimidine; sulfonamide	EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor; vasodilator agent
zaprinast zaprinast: anaphylaxis inhibitor; structure	2.01	1	0	triazolopyrimidines
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.	4.07	15	0	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger
leucovorin 5-formyltetrahydrofolic acid : A formyltetrahydrofolic acid in which the formyl group is located at position 5.	2.71	3	0	formyltetrahydrofolic acid	Escherichia coli metabolite; mouse metabolite
efrotomycin efrotomycin: from Streptomyces lactamdurans; structure	1.97	1	0
sildenafil citrate Sildenafil Citrate: A PHOSPHODIESTERASE TYPE-5 INHIBITOR; VASODILATOR AGENT and UROLOGICAL AGENT that is used in the treatment of ERECTILE DYSFUNCTION and PRIMARY PULMONARY HYPERTENSION.. sildenafil citrate : The citrate salt of sildenafil.	2.52	2	0	citrate salt	EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor; vasodilator agent
8-bromocyclic gmp 8-bromo-3',5'-cyclic GMP : A 3',5'-cyclic purine nucleotide that is 3',5'-cyclic GMP bearing an additional bromo substituent at position 8 on the guanine ring. A membrane permeable cGMP analogue that activates protein kinase G (PKG). It is 4.3-fold more potent than cGMP in activating PKG1alpha and promotes relaxation of tracheal and vascular smooth muscle tissue in vitro.	2.39	2	0	3',5'-cyclic purine nucleotide; organobromine compound	muscle relaxant; protein kinase G agonist
trypan blue Trypan Blue: A diazo-naphthalene sulfonate that is widely used as a stain.. trypan blue : An organosulfonate salt that is the tetrasodium salt of 3,3'-[(3,3'-dimethylbiphenyl-4,4'-diyl)didiazene-2,1-diyl]bis(5-amino-4-hydroxynaphthalene-2,7-disulfonic acid).	3.23	6	0
methylnitronitrosoguanidine Methylnitronitrosoguanidine: A nitrosoguanidine derivative with potent mutagenic and carcinogenic properties.. N-methyl-N'-nitro-N-nitrosoguanidine : An N-nitroguanidine compound having nitroso and methyl substituents at the N'-position	4.11	16	0	nitroso compound	alkylating agent
8-hydroxy-2'-deoxyguanosine 8-Hydroxy-2'-Deoxyguanosine: Common oxidized form of deoxyguanosine in which C-8 position of guanine base has a carbonyl group.. 8-hydroxy-2'-deoxyguanosine : Guanosine substituted at the purine 8-position by a hydroxy group. It is used as a biomarker of oxidative DNA damage.	2.43	2	0	guanosines	biomarker
8-nitroguanosine 3',5'-cyclic monophosphate 8-nitroguanosine 3',5'-cyclic monophosphate: a signal for protein S-guanylation; structure in first source. 8-nitroguanosine 3',5'-cyclic monophosphate : A 3',5'-cyclic purine nucleotide that is guanosine 3',5'-cyclic monophosphate in which the hydrogen at position 8 on the purine fragment has been replaced by a nitro group.	2.1	1	0	3',5'-cyclic purine nucleotide; C-nitro compound	biomarker; Brassica napus metabolite; human metabolite; signalling molecule
5-methyltetrahydrofolate 5-methyltetrahydrofolate : A group of heterocyclic compounds based on the 5-methyl-5,6,7,8-tetrahydropteroic acid skeleton conjugated with one or more L-glutamic acid or L-glutamate units.	1.96	1	0
enng [no description available]	1.97	1	0
liproxstatin-1 liproxstatin-1: suppress ferroptosis in cells. liproxstatin-1 : An azaspiro compound that is 1'H-spiro[piperidine-4,2'-quinoxaline] in which the hydrogen at position 3' is replaced by a (3-chlorobenzyl)amino group. It is a potent inhibitor of ferroptosis.	2.31	1	0	azaspiro compound; monochlorobenzenes; organic heterotricyclic compound; secondary amino compound	antioxidant; cardioprotective agent; ferroptosis inhibitor; radical scavenger
cholestyramine resin Cholestyramine Resin: A strongly basic anion exchange resin whose main constituent is polystyrene trimethylbenzylammonium Cl(-) anion.	9.38	66	2
eye [no description available]	2.39	2	0
tauromuricholate tauromuricholic acid: RN given refers to (3 alpha,5 beta,6 beta,7 beta)-isomer	5.78	33	0
org 6368 Org 6368: 3-monoacetate, while pancuronium is 3,17-diacetate	2.36	2	0
concanavalin a Concanavalin A: A MANNOSE/GLUCOSE binding lectin isolated from the jack bean (Canavalia ensiformis). It is a potent mitogen used to stimulate cell proliferation in lymphocytes, primarily T-lymphocyte, cultures.	1.96	1	0
trypsinogen Trypsinogen: The inactive proenzyme of trypsin secreted by the pancreas, activated in the duodenum via cleavage by enteropeptidase. (Stedman, 25th ed)	5.74	27	0
metallothionein Metallothionein: A low-molecular-weight (approx. 10 kD) protein occurring in the cytoplasm of kidney cortex and liver. It is rich in cysteinyl residues and contains no aromatic amino acids. Metallothionein shows high affinity for bivalent heavy metals.	1.99	1	0
dinitrobenzenes Dinitrobenzenes: Benzene derivatives which are substituted with two nitro groups in the ortho, meta or para positions.	2	1	0
2',7'-bis(carboxyethyl)-5(6)-carboxyfluorescein [no description available]	1.97	1	0
phosphorus radioisotopes Phosphorus Radioisotopes: Unstable isotopes of phosphorus that decay or disintegrate emitting radiation. P atoms with atomic weights 28-34 except 31 are radioactive phosphorus isotopes.	2.02	1	0
cholylglycyltyrosine cholylglycyltyrosine: used with 125I in autoradiography of rat liver bile acid transport; RN given refers to (3alpha,5alpha,7alpha,12alpha)-isomer	1.98	1	0
leptin Leptin: A 16-kDa peptide hormone secreted from WHITE ADIPOCYTES. Leptin serves as a feedback signal from fat cells to the CENTRAL NERVOUS SYSTEM in regulation of food intake, energy balance, and fat storage.	2.44	2	0
ethinyl estradiol glucuronide [no description available]	1.96	1	0
cyclo(7-aminoheptanoylphenylalanyl-tryptophyl-lysyl-benzylthreonyl) cyclosomatostatin: involved in hepatocellular transport	1.98	1	0
cholylsarcosine cholylsarcosine: structure given in first source; resistant to deconjugation & dehydroxylation	2.38	2	0
filipin Filipin: A complex of polyene antibiotics obtained from Streptomyces filipinensis. Filipin III alters membrane function by interfering with membrane sterols, inhibits mitochondrial respiration, and is proposed as an antifungal agent. Filipins I, II, and IV are less important.	1.97	1	0

Condition	Relationship Strength	Studies	Trials
Hepatocellular Carcinoma [description not available]	5.5	15	0
Cancer of Liver [description not available]	5.96	24	0
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	5.5	15	0
Liver Neoplasms Tumors or cancer of the LIVER.	5.96	24	0
Hepatoblastoma A malignant neoplasm occurring in young children, primarily in the liver, composed of tissue resembling embryonal or fetal hepatic epithelium, or mixed epithelial and mesenchymal tissues. (Stedman, 25th ed)	1.99	1	0
Bile Duct Obstruction [description not available]	11.2	145	3
Cholestasis Impairment of bile flow due to obstruction in small bile ducts (INTRAHEPATIC CHOLESTASIS) or obstruction in large bile ducts (EXTRAHEPATIC CHOLESTASIS).	11.2	145	3
Cancer of Gastrointestinal Tract [description not available]	2.67	3	0
Bile Duct Obstruction, Intrahepatic [description not available]	4.85	33	0
Cholestasis, Intrahepatic Impairment of bile flow due to injury to the HEPATOCYTES; BILE CANALICULI; or the intrahepatic bile ducts (BILE DUCTS, INTRAHEPATIC).	4.85	33	0
Innate Inflammatory Response [description not available]	4.9	32	0
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	4.9	32	0
Endotoxemia A condition characterized by the presence of ENDOTOXINS in the blood. On lysis, the outer cell wall of gram-negative bacteria enters the systemic circulation and initiates a pathophysiologic cascade of pro-inflammatory mediators.	2.92	4	0
Breast Cancer [description not available]	2.99	4	0
Breast Neoplasms Tumors or cancer of the human BREAST.	2.99	4	0
African Lymphoma [description not available]	2.01	1	0
Leukemia, Lymphocytic [description not available]	2.01	1	0
Cancer of Lung [description not available]	2.01	1	0
Malignant Melanoma [description not available]	2.01	1	0
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.	2.01	1	0
Leukemia, Lymphoid Leukemia associated with HYPERPLASIA of the lymphoid tissues and increased numbers of circulating malignant LYMPHOCYTES and lymphoblasts.	2.01	1	0
Lung Neoplasms Tumors or cancer of the LUNG.	2.01	1	0
Melanoma A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)	2.01	1	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	9.97	255	0
Osteosclerosis An abnormal hardening or increased density of bone tissue.	2.02	1	0
Adverse Drug Event [description not available]	2.45	2	0
Drug-Related Side Effects and Adverse Reactions Disorders that result from the intended use of PHARMACEUTICAL PREPARATIONS. Included in this heading are a broad variety of chemically-induced adverse conditions due to toxicity, DRUG INTERACTIONS, and metabolic effects of pharmaceuticals.	2.45	2	0
Hepatitis B Virus Infection [description not available]	5.75	9	0
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.	5.75	9	0
Acute Edematous Pancreatitis [description not available]	12.04	405	1
Pancreatitis INFLAMMATION of the PANCREAS. Pancreatitis is classified as acute unless there are computed tomographic or endoscopic retrograde cholangiopancreatographic findings of CHRONIC PANCREATITIS (International Symposium on Acute Pancreatitis, Atlanta, 1992). The two most common forms of acute pancreatitis are ALCOHOLIC PANCREATITIS and gallstone pancreatitis.	17.04	405	1
Chronic Hepatitis B [description not available]	8.64	2	0
Carcinogenesis The origin, production or development of cancer through genotypic and phenotypic changes which upset the normal balance between cell proliferation and cell death. Carcinogenesis generally requires a constellation of steps, which may occur quickly or over a period of many years.	3.85	4	0
Cirrhosis, Liver [description not available]	7.1	20	1
Liver Cirrhosis Liver disease in which the normal microcirculation, the gross vascular anatomy, and the hepatic architecture have been variably destroyed and altered with fibrous septa surrounding regenerated or regenerating parenchymal nodules.	12.1	20	1
Hepatitis B, Chronic INFLAMMATION of the LIVER in humans caused by HEPATITIS B VIRUS lasting six months or more. 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.	3.64	2	0
Failure to Thrive A condition of substandard growth or diminished capacity to maintain normal function.	3.33	1	0
Itching [description not available]	3.33	1	0
Pruritus An intense itching sensation that produces the urge to rub or scratch the skin to obtain relief.	3.33	1	0
Acute Liver Injury, Drug-Induced [description not available]	7.2	33	1
Chemical and Drug Induced Liver Injury A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.	7.2	33	1
Hepatitis, Viral, Non-A, Non-B, Parenterally-Transmitted [description not available]	2.69	2	0
HIV Coinfection [description not available]	2.53	2	0
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.	2.69	2	0
HIV Infections Includes the spectrum of human immunodeficiency virus infections that range from asymptomatic seropositivity, thru AIDS-related complex (ARC), to acquired immunodeficiency syndrome (AIDS).	2.53	2	0
Acute Disease Disease having a short and relatively severe course.	11.49	299	1
Enterically-Transmitted Non-A, Non-B Hepatitis [description not available]	2.41	1	0
Hepatitis E Acute INFLAMMATION of the LIVER in humans; caused by HEPATITIS E VIRUS, a non-enveloped single-stranded RNA virus. Similar to HEPATITIS A, its incubation period is 15-60 days and is enterically transmitted, usually by fecal-oral transmission.	2.41	1	0
Esophageal Reflux [description not available]	3.36	7	0
Tooth Erosion Progressive loss of the hard substance of a tooth by chemical processes that do not involve bacterial action. (Jablonski, Dictionary of Dentistry, 1992, p296)	2.41	1	0
Gastroesophageal Reflux Retrograde flow of gastric juice (GASTRIC ACID) and/or duodenal contents (BILE ACIDS; PANCREATIC JUICE) into the distal ESOPHAGUS, commonly due to incompetence of the LOWER ESOPHAGEAL SPHINCTER.	3.36	7	0
Colitis, Granulomatous [description not available]	7.46	29	1
Ileal Diseases Pathological development in the ILEUM including the ILEOCECAL VALVE.	3.78	11	0
Crohn Disease A chronic transmural inflammation that may involve any part of the DIGESTIVE TRACT from MOUTH to ANUS, mostly found in the ILEUM, the CECUM, and the COLON. In Crohn disease, the inflammation, extending through the intestinal wall from the MUCOSA to the serosa, is characteristically asymmetric and segmental. Epithelioid GRANULOMAS may be seen in some patients.	12.46	29	1
Diarrhea An increased liquidity or decreased consistency of FECES, such as running stool. Fecal consistency is related to the ratio of water-holding capacity of insoluble solids to total water, rather than the amount of water present. Diarrhea is not hyperdefecation or increased fecal weight.	12.13	93	1
Disbacteriosis [description not available]	2.93	3	0
Biliary Tract Cancer [description not available]	2.41	1	0
Biliary Tract Neoplasms Tumors or cancer in the BILIARY TRACT including the BILE DUCTS and the GALLBLADDER.	2.41	1	0
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	11.16	51	0
Fatty Liver, Nonalcoholic [description not available]	3.42	6	0
Non-alcoholic Fatty Liver Disease Fatty liver finding without excessive ALCOHOL CONSUMPTION.	3.42	6	0
Amazon Black Fever [description not available]	4.64	5	0
Hepatitis D INFLAMMATION of the LIVER in humans caused by HEPATITIS DELTA VIRUS, a defective RNA virus that can only infect HEPATITIS B patients. For its viral coating, hepatitis delta virus requires the HEPATITIS B SURFACE ANTIGENS produced by these patients. Hepatitis D can occur either concomitantly with (coinfection) or subsequent to (superinfection) hepatitis B infection. Similar to hepatitis B, 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.	4.64	5	0
Pericementitis [description not available]	2.6	1	0
Periodontitis Inflammation and loss of connective tissues supporting or surrounding the teeth. This may involve any part of the PERIODONTIUM. Periodontitis is currently classified by disease progression (CHRONIC PERIODONTITIS; AGGRESSIVE PERIODONTITIS) instead of age of onset. (From 1999 International Workshop for a Classification of Periodontal Diseases and Conditions, American Academy of Periodontology)	2.6	1	0
Alloxan Diabetes [description not available]	3.87	12	0
Colorectal Cancer [description not available]	3.72	9	0
Colorectal Neoplasms Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.	3.72	9	0
Cirrhosis [description not available]	2.6	1	0
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	2.6	1	0
Grippe [description not available]	2.6	1	0
Influenza, Human An acute viral infection in humans involving the respiratory tract. It is marked by inflammation of the NASAL MUCOSA; the PHARYNX; and conjunctiva, and by headache and severe, often generalized, myalgia.	2.6	1	0
Diabetes Mellitus, Adult-Onset [description not available]	3.37	6	0
Insulin Sensitivity [description not available]	3.41	6	0
Diabetes Mellitus, Type 2 A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.	3.37	6	0
Insulin Resistance Diminished effectiveness of INSULIN in lowering blood sugar levels: requiring the use of 200 units or more of insulin per day to prevent HYPERGLYCEMIA or KETOSIS.	3.41	6	0
Complications, Pregnancy [description not available]	3.76	10	0
Aura [description not available]	4.51	1	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)	4.51	1	1
Malabsorption Syndromes General term for a group of MALNUTRITION syndromes caused by failure of normal INTESTINAL ABSORPTION of nutrients.	11.15	67	1
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	6.19	12	1
Lung Injury, Acute [description not available]	4.31	17	0
Acute Lung Injury A condition of lung damage that is characterized by bilateral pulmonary infiltrates (PULMONARY EDEMA) rich in NEUTROPHILS, and in the absence of clinical HEART FAILURE. This can represent a spectrum of pulmonary lesions, endothelial and epithelial, due to numerous factors (physical, chemical, or biological).	4.31	17	0
Chronic Lung Injury [description not available]	3.59	8	0
Acute Necrotizing Pancreatitis [description not available]	7.03	116	0
Colitis, Mucous [description not available]	4.76	6	0
Steatorrhea A condition that is characterized by chronic fatty DIARRHEA, a result of abnormal DIGESTION and/or INTESTINAL ABSORPTION of FATS.	5.22	7	0
Irritable Bowel Syndrome A disorder with chronic or recurrent colonic symptoms without a clearcut etiology. This condition is characterized by chronic or recurrent ABDOMINAL PAIN, bloating, MUCUS in FECES, and an erratic disturbance of DEFECATION.	4.76	6	0
Cardiac Rupture, Traumatic [description not available]	2.25	1	0
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	10.43	62	0
Hyperlipemia [description not available]	2.25	1	0
Hyperlipidemias Conditions with excess LIPIDS in the blood.	2.25	1	0
Hypocalcemia Reduction of the blood calcium below normal. Manifestations include hyperactive deep tendon reflexes, Chvostek's sign, muscle and abdominal cramps, and carpopedal spasm. (Dorland, 27th ed)	2.42	2	0
Acute Kidney Failure [description not available]	5.18	11	1
Acute Kidney Injury Abrupt reduction in kidney function. Acute kidney injury encompasses the entire spectrum of the syndrome including acute kidney failure; ACUTE KIDNEY TUBULAR NECROSIS; and other less severe conditions.	5.18	11	1
Disease Exacerbation [description not available]	4.15	15	0
Chronic Illness [description not available]	8.56	41	1
Chronic Disease Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).	8.56	41	1
Carcinoma, Epidermoid [description not available]	2.55	2	0
Cancer of Mouth [description not available]	2.25	1	0
Carcinoma, Squamous Cell A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed)	2.55	2	0
Mouth Neoplasms Tumors or cancer of the MOUTH.	2.25	1	0
Diathesis [description not available]	2.81	3	0
Vibrio cholerae Infection [description not available]	2.93	4	0
Cholera An acute diarrheal disease endemic in India and Southeast Asia whose causative agent is VIBRIO CHOLERAE. This condition can lead to severe dehydration in a matter of hours unless quickly treated.	2.93	4	0
Cardiometabolic Syndrome A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components not only include metabolic dysfunctions of METABOLIC SYNDROME but also HYPERTENSION, and ABDOMINAL OBESITY.	2.25	1	0
Metabolic Syndrome A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components of metabolic syndrome include ABDOMINAL OBESITY; atherogenic DYSLIPIDEMIA; HYPERTENSION; HYPERGLYCEMIA; INSULIN RESISTANCE; a proinflammatory state; and a prothrombotic (THROMBOSIS) state.	2.25	1	0
Age-Related Osteoporosis [description not available]	2.31	1	0
Osteoporosis Reduction of bone mass without alteration in the composition of bone, leading to fractures. Primary osteoporosis can be of two major types: postmenopausal osteoporosis (OSTEOPOROSIS, POSTMENOPAUSAL) and age-related or senile osteoporosis.	2.31	1	0
Recrudescence [description not available]	2.55	2	0
Clostridioides difficile Infection [description not available]	3.2	5	0
Clostridium Infections Infections with bacteria of the genus CLOSTRIDIUM and closely related CLOSTRIDIOIDES species.	3.2	5	0
Injury, Ischemia-Reperfusion [description not available]	3.95	13	0
Reperfusion Injury Adverse functional, metabolic, or structural changes in tissues that result from the restoration of blood flow to the tissue (REPERFUSION) following ISCHEMIA.	3.95	13	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	4.9	36	0
Malnourishment [description not available]	2.31	1	0
Malnutrition An imbalanced nutritional status resulting from insufficient intake of nutrients to meet normal physiological requirement.	2.31	1	0
Obesity A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).	3.95	12	0
Autoimmune Diabetes [description not available]	2.84	3	0
Diabetes Mellitus, Type 1 A subtype of DIABETES MELLITUS that is characterized by INSULIN deficiency. It is manifested by the sudden onset of severe HYPERGLYCEMIA, rapid progression to DIABETIC KETOACIDOSIS, and DEATH unless treated with insulin. The disease may occur at any age, but is most common in childhood or adolescence.	2.84	3	0
Cystic Fibrosis of Pancreas [description not available]	4.6	10	0
Biliary Cirrhosis [description not available]	4.77	7	1
Cystic Fibrosis An autosomal recessive genetic disease of the EXOCRINE GLANDS. It is caused by mutations in the gene encoding the CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR expressed in several organs including the LUNG, the PANCREAS, the BILIARY SYSTEM, and the SWEAT GLANDS. Cystic fibrosis is characterized by epithelial secretory dysfunction associated with ductal obstruction resulting in AIRWAY OBSTRUCTION; chronic RESPIRATORY INFECTIONS; PANCREATIC INSUFFICIENCY; maldigestion; salt depletion; and HEAT PROSTRATION.	4.6	10	0
Liver Cirrhosis, Biliary FIBROSIS of the hepatic parenchyma due to obstruction of BILE flow (CHOLESTASIS) in the intrahepatic or extrahepatic bile ducts (BILE DUCTS, INTRAHEPATIC; BILE DUCTS, EXTRAHEPATIC). Primary biliary cholangitis involves the destruction of small intra-hepatic bile ducts and decreased bile secretion. Secondary biliary cholangitis is produced by prolonged obstruction of large intrahepatic or extrahepatic bile ducts from a variety of causes.	4.77	7	1
Benign Neoplasms [description not available]	3.71	9	0
Colicky Pain [description not available]	2.15	1	0
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	3.71	9	0
Abdominal Pain Sensation of discomfort, distress, or agony in the abdominal region.	2.15	1	0
Intestinal Diseases Pathological processes in any segment of the INTESTINE from DUODENUM to RECTUM.	3.36	7	0
MODS [description not available]	3.44	7	0
Multiple Organ Failure A progressive condition usually characterized by combined failure of several organs such as the lungs, liver, kidney, along with some clotting mechanisms, usually postinjury or postoperative.	3.44	7	0
Acute Confusional Senile Dementia [description not available]	2.51	2	0
Alzheimer Disease A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)	2.51	2	0
Injuries, Radiation [description not available]	5.22	4	1
Bowel Diseases, Inflammatory [description not available]	3.86	4	0
Inflammatory Bowel Diseases Chronic, non-specific inflammation of the GASTROINTESTINAL TRACT. Etiology may be genetic or environmental. This term includes CROHN DISEASE and ULCERATIVE COLITIS.	3.86	4	0
Inflammatory Response Syndrome, Systemic [description not available]	3.55	8	0
Cardiac Diseases [description not available]	2.17	1	0
Heart Diseases Pathological conditions involving the HEART including its structural and functional abnormalities.	2.17	1	0
Systemic Inflammatory Response Syndrome A systemic inflammatory response to a variety of clinical insults, characterized by two or more of the following conditions: (1) fever	3.55	8	0
Ascites Accumulation or retention of free fluid within the peritoneal cavity.	3.71	10	0
Neonatal Early-Onset Sepsis [description not available]	2.17	1	0
Neonatal Sepsis Blood infection that occurs in an infant younger than 90 days old. Early-onset sepsis is seen in the first week of life and most often appears within 24 hours of birth. Late-onset occurs after 1 week and before 3 months of age.	2.17	1	0
Adenocarcinoma, Basal Cell [description not available]	3.78	11	0
Cancer of Esophagus [description not available]	3.19	5	0
Invasiveness, Neoplasm [description not available]	2.81	3	0
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	3.78	11	0
Esophageal Neoplasms Tumors or cancer of the ESOPHAGUS.	3.19	5	0
Liver Dysfunction [description not available]	5.3	21	0
Liver Diseases Pathological processes of the LIVER.	5.3	21	0
Candida Infection [description not available]	2.17	1	0
Candidiasis Infection with a fungus of the genus CANDIDA. It is usually a superficial infection of the moist areas of the body and is generally caused by CANDIDA ALBICANS. (Dorland, 27th ed)	2.17	1	0
Experimental Hepatoma [description not available]	3.94	13	0
Chronic Kidney Diseases [description not available]	2.21	1	0
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.	2.4	2	0
Renal Insufficiency, Chronic Conditions in which the KIDNEYS perform below the normal level for more than three months. Chronic kidney insufficiency is classified by five stages according to the decline in GLOMERULAR FILTRATION RATE and the degree of kidney damage (as measured by the level of PROTEINURIA). The most severe form is the end-stage renal disease (CHRONIC KIDNEY FAILURE). (Kidney Foundation: Kidney Disease Outcome Quality Initiative, 2002)	2.21	1	0
Barrett Epithelium [description not available]	2.73	3	0
Barrett Esophagus A condition with damage to the lining of the lower ESOPHAGUS resulting from chronic acid reflux (ESOPHAGITIS, REFLUX). Through the process of metaplasia, the squamous cells are replaced by a columnar epithelium with cells resembling those of the INTESTINE or the salmon-pink mucosa of the STOMACH. Barrett's columnar epithelium is a marker for severe reflux and precursor to ADENOCARCINOMA of the esophagus.	2.73	3	0
Cancer of Intestines [description not available]	2.91	4	0
Intestinal Neoplasms Tumors or cancer of the INTESTINES.	2.91	4	0
Impaired Glucose Tolerance [description not available]	2.45	2	0
Glucose Intolerance A pathological state in which BLOOD GLUCOSE level is less than approximately 140 mg/100 ml of PLASMA at fasting, and above approximately 200 mg/100 ml plasma at 30-, 60-, or 90-minute during a GLUCOSE TOLERANCE TEST. This condition is seen frequently in DIABETES MELLITUS, but also occurs with other diseases and MALNUTRITION.	2.45	2	0
Biliary Calculi [description not available]	4.99	9	1
Gallstones Solid crystalline precipitates in the BILIARY TRACT, usually formed in the GALLBLADDER, resulting in the condition of CHOLELITHIASIS. Gallstones, derived from the BILE, consist mainly of calcium, cholesterol, or bilirubin.	4.99	9	1
Bone Loss, Perimenopausal [description not available]	3.47	1	1
Osteoporosis, Postmenopausal Metabolic disorder associated with fractures of the femoral neck, vertebrae, and distal forearm. It occurs commonly in women within 15-20 years after menopause, and is caused by factors associated with menopause including estrogen deficiency.	3.47	1	1
Anasarca [description not available]	5.32	21	0
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	5.32	21	0
Blood Clot [description not available]	2.08	1	0
Thrombosis Formation and development of a thrombus or blood clot in the blood vessel.	2.08	1	0
Gallstone Disease [description not available]	5.74	34	0
Cholelithiasis Presence or formation of GALLSTONES in the BILIARY TRACT, usually in the gallbladder (CHOLECYSTOLITHIASIS) or the common bile duct (CHOLEDOCHOLITHIASIS).	5.74	34	0
Kidney, Polycystic [description not available]	2.08	1	0
Polycystic Kidney Diseases Hereditary diseases that are characterized by the progressive expansion of a large number of tightly packed CYSTS within the KIDNEYS. They include diseases with autosomal dominant and autosomal recessive inheritance.	2.08	1	0
Auricular Fibrillation [description not available]	2.08	1	0
Atrial Fibrillation Abnormal cardiac rhythm that is characterized by rapid, uncoordinated firing of electrical impulses in the upper chambers of the heart (HEART ATRIA). In such case, blood cannot be effectively pumped into the lower chambers of the heart (HEART VENTRICLES). It is caused by abnormal impulse generation.	2.08	1	0
Corneal Angiogenesis [description not available]	2.52	2	0
Corneal Neovascularization New blood vessels originating from the corneal blood vessels and extending from the limbus into the adjacent CORNEAL STROMA. Neovascularization in the superficial and/or deep corneal stroma is a sequel to numerous inflammatory diseases of the ocular anterior segment, such as TRACHOMA, viral interstitial KERATITIS, microbial KERATOCONJUNCTIVITIS, and the immune response elicited by CORNEAL TRANSPLANTATION.	2.52	2	0
Hyperplasia An increase in the number of cells in a tissue or organ without tumor formation. It differs from HYPERTROPHY, which is an increase in bulk without an increase in the number of cells.	2.91	4	0
Antibiotic-Associated Colitis [description not available]	2.08	1	0
Enterocolitis, Pseudomembranous An acute inflammation of the INTESTINAL MUCOSA that is characterized by the presence of pseudomembranes or plaques in the SMALL INTESTINE (pseudomembranous enteritis) and the LARGE INTESTINE (pseudomembranous colitis). It is commonly associated with antibiotic therapy and CLOSTRIDIUM DIFFICILE colonization.	2.08	1	0
Koch's Disease [description not available]	2.1	1	0
Tuberculosis Any of the infectious diseases of man and other animals caused by species of MYCOBACTERIUM TUBERCULOSIS.	2.1	1	0
Esophageal Squamous Cell Carcinoma A carcinoma that originates usually from cells on the surface of the middle and lower third of the ESOPHAGUS. Tumor cells exhibit typical squamous morphology and form large polypoid lesions. Mutations in RNF6, LZTS1, TGFBR2, DEC1, and WWOX1 genes are associated with this cancer.	7.1	1	0
Angiogenesis, Pathologic [description not available]	3.47	7	0
Cholera Infantum [description not available]	4.14	6	0
Diabetes Mellitus A heterogeneous group of disorders characterized by HYPERGLYCEMIA and GLUCOSE INTOLERANCE.	2.9	4	0
Disease, Pulmonary [description not available]	3.1	5	0
Lung Diseases Pathological processes involving any part of the LUNG.	3.1	5	0
Genetic Predisposition [description not available]	2.73	3	0
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.	2.1	1	0
Blood Poisoning [description not available]	2.43	2	0
Sepsis Systemic inflammatory response syndrome with a proven or suspected infectious etiology. When sepsis is associated with organ dysfunction distant from the site of infection, it is called severe sepsis. When sepsis is accompanied by HYPOTENSION despite adequate fluid infusion, it is called SEPTIC SHOCK.	2.43	2	0
Atrophy Decrease in the size of a cell, tissue, organ, or multiple organs, associated with a variety of pathological conditions such as abnormal cellular changes, ischemia, malnutrition, or hormonal changes.	3.31	2	0
Hypertrophy General increase in bulk of a part or organ due to CELL ENLARGEMENT and accumulation of FLUIDS AND SECRETIONS, not due to tumor formation, nor to an increase in the number of cells (HYPERPLASIA).	2.11	1	0
Cardiac Death [description not available]	2.11	1	0
Hematologic Malignancies [description not available]	2.11	1	0
Cancer of Digestive System [description not available]	2.11	1	0
Genito-urinary Cancer [description not available]	2.11	1	0
Digestive System Neoplasms Tumors or cancer of the DIGESTIVE SYSTEM.	2.11	1	0
Urogenital Neoplasms Tumors or cancer of the UROGENITAL SYSTEM in either the male or the female.	2.11	1	0
Hematologic Neoplasms Neoplasms located in the blood and blood-forming tissue (the bone marrow and lymphatic tissue). The commonest forms are the various types of LEUKEMIA, of LYMPHOMA, and of the progressive, life-threatening forms of the MYELODYSPLASTIC SYNDROMES.	2.11	1	0
Gastric Diseases [description not available]	4	14	0
Cardiovascular Diseases Pathological conditions involving the CARDIOVASCULAR SYSTEM including the HEART; the BLOOD VESSELS; or the PERICARDIUM.	2.11	1	0
Hemorrhagic Shock [description not available]	4.75	12	0
Abdominal Injuries General or unspecified injuries involving organs in the abdominal cavity.	2.11	1	0
Atherogenesis [description not available]	2.11	1	0
Elevated Cholesterol [description not available]	5.66	10	0
Hypercholesterolemia A condition with abnormally high levels of CHOLESTEROL in the blood. It is defined as a cholesterol value exceeding the 95th percentile for the population.	5.66	10	0
Atherosclerosis A thickening and loss of elasticity of the walls of ARTERIES that occurs with formation of ATHEROSCLEROTIC PLAQUES within the ARTERIAL INTIMA.	2.11	1	0
Asthma, Bronchial [description not available]	2.11	1	0
Asthma A form of bronchial disorder with three distinct components: airway hyper-responsiveness (RESPIRATORY HYPERSENSITIVITY), airway INFLAMMATION, and intermittent AIRWAY OBSTRUCTION. It is characterized by spasmodic contraction of airway smooth muscle, WHEEZING, and dyspnea (DYSPNEA, PAROXYSMAL).	2.11	1	0
Biliary Fistula Abnormal passage in any organ of the biliary tract or between biliary organs and other organs.	4.67	29	0
ADPKD [description not available]	2.13	1	0
Polycystic Kidney, Autosomal Dominant Kidney disorders with autosomal dominant inheritance and characterized by multiple CYSTS in both KIDNEYS with progressive deterioration of renal function.	2.13	1	0
Cholangiocellular Carcinoma [description not available]	2.11	1	0
Cholangiocarcinoma A malignant tumor arising from the epithelium of the BILE DUCTS.	2.11	1	0
Cholangiitis, Sclerosing [description not available]	3.04	1	0
Cholangitis, Sclerosing Chronic inflammatory disease of the BILIARY TRACT. It is characterized by fibrosis and hardening of the intrahepatic and extrahepatic biliary ductal systems leading to bile duct strictures, CHOLESTASIS, and eventual BILIARY CIRRHOSIS.	3.04	1	0
Metastase [description not available]	2.39	2	0
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	2.39	2	0
Cancer of Colon [description not available]	4.6	10	0
Colonic Neoplasms Tumors or cancer of the COLON.	4.6	10	0
Anesthesia A state characterized by loss of feeling or sensation. This depression of nerve function is usually the result of pharmacologic action and is induced to allow performance of surgery or other painful procedures.	2.89	4	0
Colitis Gravis [description not available]	4.5	9	0
Colitis, Ulcerative Inflammation of the COLON that is predominantly confined to the MUCOSA. Its major symptoms include DIARRHEA, rectal BLEEDING, the passage of MUCUS, and ABDOMINAL PAIN.	4.5	9	0
Experimental Lung Inflammation Inflammation of any part, segment or lobe, of the lung parenchyma.	2.75	3	0
Pneumonia Infection of the lung often accompanied by inflammation.	2.75	3	0
Diseases, Metabolic [description not available]	2.15	1	0
Metabolic Diseases Generic term for diseases caused by an abnormal metabolic process. It can be congenital due to inherited enzyme abnormality (METABOLISM, INBORN ERRORS) or acquired due to disease of an endocrine organ or failure of a metabolically important organ such as the liver. (Stedman, 26th ed)	2.15	1	0
Fish Diseases Diseases of freshwater, marine, hatchery or aquarium fish. This term includes diseases of both teleosts (true fish) and elasmobranchs (sharks, rays and skates).	2.15	1	0
Fasciolopsiasis [description not available]	2.15	1	0
Shock, Cardiogenic Shock resulting from diminution of cardiac output in heart disease.	2.04	1	0
Adrenal Gland Hypofunction [description not available]	2.04	1	0
Adrenal Insufficiency Conditions in which the production of adrenal CORTICOSTEROIDS falls below the requirement of the body. Adrenal insufficiency can be caused by defects in the ADRENAL GLANDS, the PITUITARY GLAND, or the HYPOTHALAMUS.	2.04	1	0
Extravascular Hemolysis [description not available]	4.03	15	0
Hemolysis The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.	4.03	15	0
Blood Pressure, Low [description not available]	2.89	4	0
Hypotension Abnormally low BLOOD PRESSURE that can result in inadequate blood flow to the brain and other vital organs. Common symptom is DIZZINESS but greater negative impacts on the body occur when there is prolonged depravation of oxygen and nutrients.	2.89	4	0
Amyloidosis A group of sporadic, familial and/or inherited, degenerative, and infectious disease processes, linked by the common theme of abnormal protein folding and deposition of AMYLOID. As the amyloid deposits enlarge they displace normal tissue structures, causing disruption of function. Various signs and symptoms depend on the location and size of the deposits.	2.41	2	0
A-alphalipoprotein Neuropathy [description not available]	2.05	1	0
Edema, Pulmonary [description not available]	3.7	10	0
Pulmonary Edema Excessive accumulation of extravascular fluid in the lung, an indication of a serious underlying disease or disorder. Pulmonary edema prevents efficient PULMONARY GAS EXCHANGE in the PULMONARY ALVEOLI, and can be life-threatening.	3.7	10	0
Acid beta-Glucosidase Deficiency [description not available]	4.56	26	0
Gaucher Disease An autosomal recessive disorder caused by a deficiency of acid beta-glucosidase (GLUCOSYLCERAMIDASE) leading to intralysosomal accumulation of glycosylceramide mainly in cells of the MONONUCLEAR PHAGOCYTE SYSTEM. The characteristic Gaucher cells, glycosphingolipid-filled HISTIOCYTES, displace normal cells in BONE MARROW and visceral organs causing skeletal deterioration, hepatosplenomegaly, and organ dysfunction. There are several subtypes based on the presence and severity of neurological involvement.	4.56	26	0
Animal Mammary Carcinoma [description not available]	2.05	1	0
Mushroom Poisoning Poisoning from ingestion of mushrooms, primarily from, but not restricted to, toxic varieties.	2.05	1	0
Oral Submucous Fibrosis Irreversible FIBROSIS of the submucosal tissue of the MOUTH.	2.05	1	0
Splenic Diseases Diseases involving the SPLEEN.	2.05	1	0
Deficiency, Pyridoxine [description not available]	2.38	2	0
Jaundice, Cholestatic [description not available]	2.37	2	0
Jaundice, Obstructive Jaundice, the condition with yellowish staining of the skin and mucous membranes, that is due to impaired BILE flow in the BILIARY TRACT, such as INTRAHEPATIC CHOLESTASIS, or EXTRAHEPATIC CHOLESTASIS.	2.37	2	0
Adenoma, Basal Cell [description not available]	2.89	4	0
Adenoma A benign epithelial tumor with a glandular organization.	2.89	4	0
Fat Necrosis A condition in which the death of adipose tissue results in neutral fats being split into fatty acids and glycerol.	2.71	3	0
Fistula Abnormal communication most commonly seen between two internal organs, or between an internal organ and the surface of the body.	2.66	3	0
Carbon Tetrachloride Poisoning Poisoning that results from ingestion, injection, inhalation, or skin absorption of CARBON TETRACHLORIDE.	3.23	6	0
E coli Infections [description not available]	2.43	2	0
Escherichia coli Infections Infections with bacteria of the species ESCHERICHIA COLI.	2.43	2	0
Chronic Pancreatitis [description not available]	2.06	1	0
Pancreatitis, Chronic INFLAMMATION of the PANCREAS that is characterized by recurring or persistent ABDOMINAL PAIN with or without STEATORRHEA or DIABETES MELLITUS. It is characterized by the irregular destruction of the pancreatic parenchyma which may be focal, segmental, or diffuse.	2.06	1	0
Muscle Relaxation That phase of a muscle twitch during which a muscle returns to a resting position.	2.68	3	0
Electron Transport Chain Deficiencies, Mitochondrial [description not available]	2.06	1	0
Mitochondrial Diseases Diseases caused by abnormal function of the MITOCHONDRIA. They may be caused by mutations, acquired or inherited, in mitochondrial DNA or in nuclear genes that code for mitochondrial components. They may also be the result of acquired mitochondria dysfunction due to adverse effects of drugs, infections, or other environmental causes.	2.06	1	0
Constriction, Pathological [description not available]	2.7	3	0
Constriction, Pathologic The condition of an anatomical structure's being constricted beyond normal dimensions.	2.7	3	0
Electrolytes Substances that dissociate into two or more ions, to some extent, in water. Solutions of electrolytes thus conduct an electric current and can be decomposed by it (ELECTROLYSIS). (Grant & Hackh's Chemical Dictionary, 5th ed)	4.04	15	0
Kidney Failure A severe irreversible decline in the ability of kidneys to remove wastes, concentrate URINE, and maintain ELECTROLYTE BALANCE; BLOOD PRESSURE; and CALCIUM metabolism.	2.07	1	0
Acute Hypercapnic Respiratory Failure [description not available]	2.41	2	0
Hepatic Failure [description not available]	2.07	1	0
Respiratory Insufficiency Failure to adequately provide oxygen to cells of the body and to remove excess carbon dioxide from them. (Stedman, 25th ed)	2.41	2	0
Liver Failure Severe inability of the LIVER to perform its normal metabolic functions, as evidenced by severe JAUNDICE and abnormal serum levels of AMMONIA; BILIRUBIN; ALKALINE PHOSPHATASE; ASPARTATE AMINOTRANSFERASE; LACTATE DEHYDROGENASES; and albumin/globulin ratio. (Blakiston's Gould Medical Dictionary, 4th ed)	2.07	1	0
Renal Insufficiency Conditions in which the KIDNEYS perform below the normal level in the ability to remove wastes, concentrate URINE, and maintain ELECTROLYTE BALANCE; BLOOD PRESSURE; and CALCIUM metabolism. Renal insufficiency can be classified by the degree of kidney damage (as measured by the level of PROTEINURIA) and reduction in GLOMERULAR FILTRATION RATE.	2.07	1	0
Colitis Inflammation of the COLON section of the large intestine (INTESTINE, LARGE), usually with symptoms such as DIARRHEA (often with blood and mucus), ABDOMINAL PAIN, and FEVER.	8.11	5	0
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	4.54	25	0
Cancer of Prostate [description not available]	3.46	1	1
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	3.46	1	1
Atresia, Biliary [description not available]	2.07	1	0
Icterus Gravis Neonatorum [description not available]	2.07	1	0
Biliary Atresia Progressive destruction or the absence of all or part of the extrahepatic BILE DUCTS, resulting in the complete obstruction of BILE flow. Usually, biliary atresia is found in infants and accounts for one third of the neonatal cholestatic JAUNDICE.	2.07	1	0
Jaundice, Neonatal Yellow discoloration of the SKIN; MUCOUS MEMBRANE; and SCLERA in the NEWBORN. It is a sign of NEONATAL HYPERBILIRUBINEMIA. Most cases are transient self-limiting (PHYSIOLOGICAL NEONATAL JAUNDICE) occurring in the first week of life, but some can be a sign of pathological disorders, particularly LIVER DISEASES.	2.07	1	0
Bleeding [description not available]	4.46	23	0
Hemorrhage Bleeding or escape of blood from a vessel.	4.46	23	0
Atheroma [description not available]	2.08	1	0
Diseases of Immune System [description not available]	2.08	1	0
Immune System Diseases Disorders caused by abnormal or absent immunologic mechanisms, whether humoral, cell-mediated, or both.	2.08	1	0
Fetal Death Death of the developing young in utero. BIRTH of a dead FETUS is STILLBIRTH.	2.67	3	0
Anoxemia [description not available]	3.07	5	0
Hypoxia Sub-optimal OXYGEN levels in the ambient air of living organisms.	3.07	5	0
7-Dehydrocholesterol Reductase Deficiency [description not available]	3.39	1	1
Actinic Reticuloid Syndrome [description not available]	3.39	1	1
Polyneuropathy, Acquired [description not available]	3.39	1	1
Polyneuropathies Diseases of multiple peripheral nerves simultaneously. Polyneuropathies usually are characterized by symmetrical, bilateral distal motor and sensory impairment with a graded increase in severity distally. The pathological processes affecting peripheral nerves include degeneration of the axon, myelin or both. The various forms of polyneuropathy are categorized by the type of nerve affected (e.g., sensory, motor, or autonomic), by the distribution of nerve injury (e.g., distal vs. proximal), by nerve component primarily affected (e.g., demyelinating vs. axonal), by etiology, or by pattern of inheritance.	3.39	1	1
Smith-Lemli-Opitz Syndrome An autosomal recessive disorder of CHOLESTEROL metabolism. It is caused by a deficiency of 7-dehydrocholesterol reductase, the enzyme that converts 7-dehydrocholesterol to cholesterol, leading to an abnormally low plasma cholesterol. This syndrome is characterized by multiple CONGENITAL ABNORMALITIES, growth deficiency, and INTELLECTUAL DISABILITY.	3.39	1	1
Alcoholic Cirrhosis [description not available]	2.38	2	0
Liver Cirrhosis, Alcoholic FIBROSIS of the hepatic parenchyma due to chronic excess ALCOHOL DRINKING.	2.38	2	0
Ischemia A hypoperfusion of the BLOOD through an organ or tissue caused by a PATHOLOGIC CONSTRICTION or obstruction of its BLOOD VESSELS, or an absence of BLOOD CIRCULATION.	6.28	14	1
Acute Respiratory Distress Syndrome [description not available]	3.1	5	0
Respiratory Distress Syndrome A syndrome characterized by progressive life-threatening RESPIRATORY INSUFFICIENCY in the absence of known LUNG DISEASES, usually following a systemic insult such as surgery or major TRAUMA.	3.1	5	0
Bacterial Disease [description not available]	3.5	8	0
Bacterial Infections Infections by bacteria, general or unspecified.	3.5	8	0
Arrhythmia [description not available]	2.42	2	0
Arrhythmias, Cardiac Any disturbances of the normal rhythmic beating of the heart or MYOCARDIAL CONTRACTION. Cardiac arrhythmias can be classified by the abnormalities in HEART RATE, disorders of electrical impulse generation, or impulse conduction.	2.42	2	0
Delayed Effects, Prenatal Exposure [description not available]	2.01	1	0
Active Hyperemia [description not available]	2.69	3	0
Hyperemia The presence of an increased amount of blood in a body part or an organ leading to congestion or engorgement of blood vessels. Hyperemia can be due to increase of blood flow into the area (active or arterial), or due to obstruction of outflow of blood from the area (passive or venous).	2.69	3	0
Experimental Neoplasms [description not available]	3.05	5	0
Cancer of Skin [description not available]	1.93	1	0
Skin Neoplasms Tumors or cancer of the SKIN.	1.93	1	0
Calciphylaxes [description not available]	1.94	1	0
Hyperglycemia, Postprandial Abnormally high BLOOD GLUCOSE level after a meal.	3.79	2	1
Ovine Diseases [description not available]	5.18	4	1
Hyperglycemia Abnormally high BLOOD GLUCOSE level.	3.79	2	1
Bile Duct Obstruction, Extrahepatic [description not available]	3.92	13	0
Bilirubinemia [description not available]	3.49	8	0
Cardiovascular Pregnancy Complications [description not available]	2.02	1	0
Brain Damage, Chronic A condition characterized by long-standing brain dysfunction or damage, usually of three months duration or longer. Potential etiologies include BRAIN INFARCTION; certain NEURODEGENERATIVE DISORDERS; CRANIOCEREBRAL TRAUMA; ANOXIA, BRAIN; ENCEPHALITIS; certain NEUROTOXICITY SYNDROMES; metabolic disorders (see BRAIN DISEASES, METABOLIC); and other conditions.	2.02	1	0
Adipocere [description not available]	2.02	1	0
Acquired Immune Deficiency Syndrome [description not available]	2.02	1	0
Cryptosporidium Infection [description not available]	3.09	5	0
Acquired Immunodeficiency Syndrome An acquired defect of cellular immunity associated with infection by the human immunodeficiency virus (HIV), a CD4-positive T-lymphocyte count under 200 cells/microliter or less than 14% of total lymphocytes, and increased susceptibility to opportunistic infections and malignant neoplasms. Clinical manifestations also include emaciation (wasting) and dementia. These elements reflect criteria for AIDS as defined by the CDC in 1993.	2.02	1	0
Cryptosporidiosis Intestinal infection with organisms of the genus CRYPTOSPORIDIUM. It occurs in both animals and humans. Symptoms include severe DIARRHEA.	3.09	5	0
Bile Reflux Retrograde bile flow. Reflux of bile can be from the duodenum to the stomach (DUODENOGASTRIC REFLUX); to the esophagus (GASTROESOPHAGEAL REFLUX); or to the PANCREAS.	3.48	8	0
Laryngitis Inflammation of the LARYNGEAL MUCOSA, including the VOCAL CORDS. Laryngitis is characterized by irritation, edema, and reduced pliability of the mucosa leading to VOICE DISORDERS such as APHONIA and HOARSENESS.	2.02	1	0
Gastric Ulcer [description not available]	6.28	59	0
Stomach Ulcer Ulceration of the GASTRIC MUCOSA due to contact with GASTRIC JUICE. It is often associated with HELICOBACTER PYLORI infection or consumption of nonsteroidal anti-inflammatory drugs (NSAIDS).	6.28	59	0
Duodenal Reflux [description not available]	4.28	4	1
Gastritis Inflammation of the GASTRIC MUCOSA, a lesion observed in a number of unrelated disorders.	4.45	23	0
Aspiration, Meconium [description not available]	2.03	1	0
Meconium Aspiration Syndrome A condition caused by inhalation of MECONIUM into the LUNG of FETUS or NEWBORN, usually due to vigorous respiratory movements during difficult PARTURITION or respiratory system abnormalities. Meconium aspirate may block small airways leading to difficulties in PULMONARY GAS EXCHANGE and ASPIRATION PNEUMONIA.	2.03	1	0
Bovine Diseases [description not available]	2.03	1	0
Biliary Tract Diseases Diseases in any part of the BILIARY TRACT including the BILE DUCTS and the GALLBLADDER.	4.58	10	0
Liver Steatosis [description not available]	2.38	2	0
Fatty Liver Lipid infiltration of the hepatic parenchymal cells resulting in a yellow-colored liver. The abnormal lipid accumulation is usually in the form of TRIGLYCERIDES, either as a single large droplet or multiple small droplets. Fatty liver is caused by an imbalance in the metabolism of FATTY ACIDS.	2.38	2	0
Muscle Contraction A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.	3.76	11	0
Cancer of Pancreas [description not available]	1.96	1	0
Pancreatic Neoplasms Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).	1.96	1	0
Adult Sandhoff Disease [description not available]	2.37	2	0
Amaurotic Familial Idiocy An outdated term for Tay-Sachs disease.	2.37	2	0
Sandhoff Disease An autosomal recessive neurodegenerative disorder characterized by an accumulation of G(M2) GANGLIOSIDE in neurons and other tissues. It is caused by mutation in the common beta subunit of HEXOSAMINIDASE A and HEXOSAMINIDASE B. Thus this disease is also known as the O variant since both hexosaminidase A and B are missing. Clinically, it is indistinguishable from TAY-SACHS DISEASE.	2.37	2	0
Tay-Sachs Disease An autosomal recessive neurodegenerative disorder characterized by the onset in infancy of an exaggerated startle response, followed by paralysis, dementia, and blindness. It is caused by mutation in the alpha subunit of the HEXOSAMINIDASE A resulting in lipid-laden ganglion cells. It is also known as the B variant (with increased HEXOSAMINIDASE B but absence of hexosaminidase A) and is strongly associated with Ashkenazic Jewish ancestry.	2.37	2	0
Esophagitis INFLAMMATION, acute or chronic, of the ESOPHAGUS caused by BACTERIA, chemicals, or TRAUMA.	2.87	4	0
Hematochezia The passage of bright red blood from the rectum. The blood may or may not be mixed with formed stool in the form of blood, blood clots, bloody stool or diarrhea.	3.34	7	0
Gastrointestinal Hemorrhage Bleeding in any segment of the GASTROINTESTINAL TRACT from ESOPHAGUS to RECTUM.	3.34	7	0
Soft Tissue Neoplasms Neoplasms of whatever cell type or origin, occurring in the extraskeletal connective tissue framework of the body including the organs of locomotion and their various component structures, such as nerves, blood vessels, lymphatics, etc.	1.96	1	0
Cancer of Stomach [description not available]	3.68	10	0
Stomach Neoplasms Tumors or cancer of the STOMACH.	3.68	10	0
Esophagitis, Reflux [description not available]	3.35	7	0
Esophagitis, Peptic INFLAMMATION of the ESOPHAGUS that is caused by the reflux of GASTRIC JUICE with contents of the STOMACH and DUODENUM.	3.35	7	0
Cancer of Pelvis [description not available]	1.96	1	0
Giardia duodenalis Infection [description not available]	1.96	1	0
Giardiasis An infection of the SMALL INTESTINE caused by the flagellated protozoan GIARDIA. It is spread via contaminated food and water and by direct person-to-person contact.	1.96	1	0
Chronic Hepatitis [description not available]	2.66	3	0
Hepatitis, Chronic INFLAMMATION of the LIVER with ongoing hepatocellular injury for 6 months or more, characterized by NECROSIS of HEPATOCYTES and inflammatory cell (LEUKOCYTES) infiltration. Chronic hepatitis can be caused by viruses, medications, autoimmune diseases, and other unknown factors.	2.66	3	0
Cancer of Duodenum [description not available]	1.96	1	0
Angiosarcoma [description not available]	1.96	1	0
Cocarcinogenesis The combination of two or more different factors in the production of cancer.	2.88	4	0
Hemangiosarcoma A rare malignant neoplasm characterized by rapidly proliferating, extensively infiltrating, anaplastic cells derived from blood vessels and lining irregular blood-filled or lumpy spaces. (Stedman, 25th ed)	1.96	1	0
Rupture, Spontaneous Tear or break of an organ, vessel or other soft part of the body, occurring in the absence of external force.	1.96	1	0
Cruveilhier-Baumgarten Syndrome Liver cirrhosis with intrahepatic portal obstruction, HYPERTENSION, and patent UMBILICAL VEINS.	2.88	4	0
Hypertension, Portal Abnormal increase of resistance to blood flow within the hepatic PORTAL SYSTEM, frequently seen in LIVER CIRRHOSIS and conditions with obstruction of the PORTAL VEIN.	2.88	4	0
Curling Ulcer Acute stress DUODENAL ULCER, usually observed in patients with extensive third-degree burns.	3.22	6	0
Duodenal Ulcer A PEPTIC ULCER located in the DUODENUM.	3.22	6	0
Leiomyosarcoma, Epithelioid [description not available]	1.96	1	0
Leiomyosarcoma A sarcoma containing large spindle cells of smooth muscle. Although it rarely occurs in soft tissue, it is common in the viscera. It is the most common soft tissue sarcoma of the gastrointestinal tract and uterus. The median age of patients is 60 years. (From Dorland, 27th ed; Holland et al., Cancer Medicine, 3d ed, p1865)	1.96	1	0
Gastric Fistula Abnormal passage communicating with the STOMACH.	2.64	3	0
Cholecystoduodenal Fistula [description not available]	2.37	2	0
Niemann-Pick Disease [description not available]	2.37	2	0
Niemann-Pick Diseases A group of autosomal recessive disorders in which harmful quantities of lipids accumulate in the viscera and the central nervous system. They can be caused by deficiencies of enzyme activities (SPHINGOMYELIN PHOSPHODIESTERASE) or defects in intracellular transport, resulting in the accumulation of SPHINGOMYELINS and CHOLESTEROL. There are various subtypes based on their clinical and genetic differences.	2.37	2	0
Marasmus [description not available]	2.36	2	0
Protein-Energy Malnutrition The lack of sufficient energy or protein to meet the body's metabolic demands, as a result of either an inadequate dietary intake of protein, intake of poor quality dietary protein, increased demands due to disease, or increased nutrient losses.	2.36	2	0
Colonic Diseases Pathological processes in the COLON region of the large intestine (INTESTINE, LARGE).	1.96	1	0
Cell Transformation, Neoplastic Cell changes manifested by escape from control mechanisms, increased growth potential, alterations in the cell surface, karyotypic abnormalities, morphological and biochemical deviations from the norm, and other attributes conferring the ability to invade, metastasize, and kill.	1.96	1	0
Bilateral Headache [description not available]	1.96	1	0
Headache The symptom of PAIN in the cranial region. It may be an isolated benign occurrence or manifestation of a wide variety of HEADACHE DISORDERS.	1.96	1	0
Nausea An unpleasant sensation in the stomach usually accompanied by the urge to vomit. Common causes are early pregnancy, sea and motion sickness, emotional stress, intense pain, food poisoning, and various enteroviruses.	1.96	1	0
Equine Diseases [description not available]	1.96	1	0
Complication, Postoperative [description not available]	5.23	12	1
Postoperative Complications Pathologic processes that affect patients after a surgical procedure. They may or may not be related to the disease for which the surgery was done, and they may or may not be direct results of the surgery.	5.23	12	1
Embolism, Fat Blocking of a blood vessel by fat deposits in the circulation. It is often seen after fractures of large bones or after administration of CORTICOSTEROIDS.	1.95	1	0
Blood Pressure, High [description not available]	2.38	2	0
Hypertension Persistently high systemic arterial BLOOD PRESSURE. Based on multiple readings (BLOOD PRESSURE DETERMINATION), hypertension is currently defined as when SYSTOLIC PRESSURE is consistently greater than 140 mm Hg or when DIASTOLIC PRESSURE is consistently 90 mm Hg or more.	2.38	2	0
Stunted Growth [description not available]	1.95	1	0
Growth Disorders Deviations from the average values for a specific age and sex in any or all of the following: height, weight, skeletal proportions, osseous development, or maturation of features. Included here are both acceleration and retardation of growth.	1.95	1	0
Empyema, Gall Bladder [description not available]	1.95	1	0
Cholecystitis Inflammation of the GALLBLADDER; generally caused by impairment of BILE flow, GALLSTONES in the BILIARY TRACT, infections, or other diseases.	1.95	1	0
Cirrhoses, Experimental Liver [description not available]	3.36	7	0
AIDS Enteropathy [description not available]	2.68	3	0
AIDS-Related Opportunistic Infections Opportunistic infections found in patients who test positive for human immunodeficiency virus (HIV). The most common include PNEUMOCYSTIS PNEUMONIA, Kaposi's sarcoma, cryptosporidiosis, herpes simplex, toxoplasmosis, cryptococcosis, and infections with Mycobacterium avium complex, Microsporidium, and Cytomegalovirus.	2.39	2	0
Endotoxin Shock [description not available]	1.98	1	0
Shock, Septic Sepsis associated with HYPOTENSION or hypoperfusion despite adequate fluid resuscitation. Perfusion abnormalities may include but are not limited to LACTIC ACIDOSIS; OLIGURIA; or acute alteration in mental status.	1.98	1	0
Pancreatic Insufficiency [description not available]	1.98	1	0
Exocrine Pancreatic Insufficiency A malabsorption condition resulting from greater than 10% reduction in the secretion of pancreatic digestive enzymes (LIPASE; PROTEASES; and AMYLASE) by the EXOCRINE PANCREAS into the DUODENUM. This condition is often associated with CYSTIC FIBROSIS and with chronic PANCREATITIS.	1.98	1	0
Cerebral Pseudosclerosis [description not available]	2.37	2	0
Congenital Hypocupremia [description not available]	1.98	1	0
Hepatolenticular Degeneration A rare autosomal recessive disease characterized by the deposition of copper in the BRAIN; LIVER; CORNEA; and other organs. It is caused by defects in the ATP7B gene encoding copper-transporting ATPase 2 (EC 3.6.3.4), also known as the Wilson disease protein. The overload of copper inevitably leads to progressive liver and neurological dysfunction such as LIVER CIRRHOSIS; TREMOR; ATAXIA and intellectual deterioration. Hepatic dysfunction may precede neurologic dysfunction by several years.	2.37	2	0
Menkes Kinky Hair Syndrome An inherited disorder of copper metabolism transmitted as an X-linked trait and characterized by the infantile onset of HYPOTHERMIA, feeding difficulties, hypotonia, SEIZURES, bony deformities, pili torti (twisted hair), and severely impaired intellectual development. Defective copper transport across plasma and endoplasmic reticulum membranes results in copper being unavailable for the synthesis of several copper containing enzymes, including PROTEIN-LYSINE 6-OXIDASE; CERULOPLASMIN; and SUPEROXIDE DISMUTASE. Pathologic changes include defects in arterial elastin, neuronal loss, and gliosis. (From Menkes, Textbook of Child Neurology, 5th ed, p125)	1.98	1	0
Gastritis, Atrophic GASTRITIS with atrophy of the GASTRIC MUCOSA, the GASTRIC PARIETAL CELLS, and the mucosal glands leading to ACHLORHYDRIA. Atrophic gastritis usually progresses from chronic gastritis.	3.07	5	0
Starvation Lengthy and continuous deprivation of food. (Stedman, 25th ed)	2.87	4	0
Basedow Disease [description not available]	1.98	1	0
Graves Disease A common form of hyperthyroidism with a diffuse hyperplastic GOITER. It is an autoimmune disorder that produces antibodies against the THYROID STIMULATING HORMONE RECEPTOR. These autoantibodies activate the TSH receptor, thereby stimulating the THYROID GLAND and hypersecretion of THYROID HORMONES. These autoantibodies can also affect the eyes (GRAVES OPHTHALMOPATHY) and the skin (Graves dermopathy).	1.98	1	0
Pancreatic Diseases Pathological processes of the PANCREAS.	2.89	4	0
Colonic Diseases, Functional Chronic or recurrent colonic disorders without an identifiable structural or biochemical explanation. The widely recognized IRRITABLE BOWEL SYNDROME falls into this category.	2.89	4	0
Colonic Inertia Symptom characterized by the passage of stool once a week or less.	2.67	3	0
Adenomatous Polyposis Coli, Familial [description not available]	1.98	1	0
Cancer of Rectum [description not available]	2.37	2	0
Constipation Infrequent or difficult evacuation of FECES. These symptoms are associated with a variety of causes, including low DIETARY FIBER intake, emotional or nervous disturbances, systemic and structural disorders, drug-induced aggravation, and infections.	2.67	3	0
Adenomatous Polyposis Coli A polyposis syndrome due to an autosomal dominant mutation of the APC genes (GENES, APC) on CHROMOSOME 5. The syndrome is characterized by the development of hundreds of ADENOMATOUS POLYPS in the COLON and RECTUM of affected individuals by early adulthood.	1.98	1	0
Rectal Neoplasms Tumors or cancer of the RECTUM.	2.37	2	0
Cholangitis Inflammation of the biliary ductal system (BILE DUCTS); intrahepatic, extrahepatic, or both.	1.98	1	0
Fasciola Infection [description not available]	1.98	1	0
Fascioliasis Liver disease caused by infections with parasitic flukes of the genus FASCIOLA, such as FASCIOLA HEPATICA.	1.98	1	0
Bile Duct Cancer [description not available]	2.66	3	0
Cholangioma [description not available]	2.38	2	0
Bile Duct Neoplasms Tumors or cancer of the BILE DUCTS.	2.66	3	0
Adenoma, Bile Duct A benign tumor of the intrahepatic bile ducts.	2.38	2	0
Hyperbilirubinemia, Hereditary Inborn errors of bilirubin metabolism resulting in excessive amounts of bilirubin in the circulating blood, either because of increased bilirubin production or because of delayed clearance of bilirubin from the blood.	2.88	4	0
Cytomegalovirus A genus of the family HERPESVIRIDAE, subfamily BETAHERPESVIRINAE, infecting the salivary glands, liver, spleen, lungs, eyes, and other organs, in which they produce characteristically enlarged cells with intranuclear inclusions. Infection with Cytomegalovirus is also seen as an opportunistic infection in AIDS.	1.99	1	0
Common Bile Duct Diseases Diseases of the COMMON BILE DUCT including the AMPULLA OF VATER and the SPHINCTER OF ODDI.	2.4	2	0
Infection [description not available]	1.99	1	0
Infections Invasion of the host organism by microorganisms or their toxins or by parasites that can cause pathological conditions or diseases.	1.99	1	0
Arteriosclerosis Thickening and loss of elasticity of the walls of ARTERIES of all sizes. There are many forms classified by the types of lesions and arteries involved, such as ATHEROSCLEROSIS with fatty lesions in the ARTERIAL INTIMA of medium and large muscular arteries.	1.98	1	0
Gastroduodenal Ulcer [description not available]	2.37	2	0
Peptic Ulcer Ulcer that occurs in the regions of the GASTROINTESTINAL TRACT which come into contact with GASTRIC JUICE containing PEPSIN and GASTRIC ACID. It occurs when there are defects in the MUCOSA barrier. The common forms of peptic ulcers are associated with HELICOBACTER PYLORI and the consumption of nonsteroidal anti-inflammatory drugs (NSAIDS).	7.37	2	0
Alcohol Abuse [description not available]	3.06	5	0
Alcoholism A primary, chronic disease with genetic, psychosocial, and environmental factors influencing its development and manifestations. The disease is often progressive and fatal. It is characterized by impaired control over drinking, preoccupation with the drug alcohol, use of alcohol despite adverse consequences, and distortions in thinking, most notably denial. Each of these symptoms may be continuous or periodic. (Morse & Flavin for the Joint Commission of the National Council on Alcoholism and Drug Dependence and the American Society of Addiction Medicine to Study the Definition and Criteria for the Diagnosis of Alcoholism: in JAMA 1992;268:1012-4)	3.06	5	0
Enteritis Inflammation of any segment of the SMALL INTESTINE.	1.99	1	0
Hypertriglyceridemia A condition of elevated levels of TRIGLYCERIDES in the blood.	1.99	1	0
Lipid Metabolism, Inborn Error [description not available]	2.65	3	0
Alcoholic Pancreatitis [description not available]	2.4	2	0
Left Ventricular Hypertrophy [description not available]	1.99	1	0
Hypertrophy, Left Ventricular Enlargement of the LEFT VENTRICLE of the heart. This increase in ventricular mass is attributed to sustained abnormal pressure or volume loads and is a contributor to cardiovascular morbidity and mortality.	1.99	1	0
Alcohol Drinking Behaviors associated with the ingesting of ALCOHOLIC BEVERAGES, including social drinking.	1.99	1	0
Anemia A reduction in the number of circulating ERYTHROCYTES or in the quantity of HEMOGLOBIN.	1.99	1	0
Health Care Associated Infection [description not available]	1.99	1	0
Cross Infection Any infection which a patient contracts in a health-care institution.	1.99	1	0
Brain Swelling [description not available]	1.99	1	0
Brain Inflammation [description not available]	1.99	1	0
Brain Edema Increased intracellular or extracellular fluid in brain tissue. Cytotoxic brain edema (swelling due to increased intracellular fluid) is indicative of a disturbance in cell metabolism, and is commonly associated with hypoxic or ischemic injuries (see HYPOXIA, BRAIN). An increase in extracellular fluid may be caused by increased brain capillary permeability (vasogenic edema), an osmotic gradient, local blockages in interstitial fluid pathways, or by obstruction of CSF flow (e.g., obstructive HYDROCEPHALUS). (From Childs Nerv Syst 1992 Sep; 8(6):301-6)	1.99	1	0
Encephalitis Inflammation of the BRAIN due to infection, autoimmune processes, toxins, and other conditions. Viral infections (see ENCEPHALITIS, VIRAL) are a relatively frequent cause of this condition.	1.99	1	0
Encephalopathy, Hepatic [description not available]	1.99	1	0
Hepatic Encephalopathy A syndrome characterized by central nervous system dysfunction in association with LIVER FAILURE, including portal-systemic shunts. Clinical features include lethargy and CONFUSION (frequently progressing to COMA); ASTERIXIS; NYSTAGMUS, PATHOLOGIC; brisk oculovestibular reflexes; decorticate and decerebrate posturing; MUSCLE SPASTICITY; and bilateral extensor plantar reflexes (see REFLEX, BABINSKI). ELECTROENCEPHALOGRAPHY may demonstrate triphasic waves. (From Adams et al., Principles of Neurology, 6th ed, pp1117-20; Plum & Posner, Diagnosis of Stupor and Coma, 3rd ed, p222-5)	1.99	1	0
Bile Duct Diseases Diseases in any part of the ductal system of the BILIARY TRACT from the smallest BILE CANALICULI to the largest COMMON BILE DUCT.	1.99	1	0
Congenital Myotonic Dystrophy [description not available]	1.99	1	0
Myotonic Dystrophy Neuromuscular disorder characterized by PROGRESSIVE MUSCULAR ATROPHY; MYOTONIA, and various multisystem atrophies. Mild INTELLECTUAL DISABILITY may also occur. Abnormal TRINUCLEOTIDE REPEAT EXPANSION in the 3' UNTRANSLATED REGIONS of DMPK PROTEIN gene is associated with Myotonic Dystrophy 1. DNA REPEAT EXPANSION of zinc finger protein-9 gene intron is associated with Myotonic Dystrophy 2.	1.99	1	0
Fasting Hypoglycemia HYPOGLYCEMIA expressed in the postabsorptive state, after prolonged FASTING, or an overnight fast.	2	1	0
Hypoglycemia A syndrome of abnormally low BLOOD GLUCOSE level. Clinical hypoglycemia has diverse etiologies. Severe hypoglycemia eventually lead to glucose deprivation of the CENTRAL NERVOUS SYSTEM resulting in HUNGER; SWEATING; PARESTHESIA; impaired mental function; SEIZURES; COMA; and even DEATH.	2	1	0
Canine Diseases [description not available]	2.88	4	0
Infections, Staphylococcal [description not available]	2	1	0
Staphylococcal Infections Infections with bacteria of the genus STAPHYLOCOCCUS.	2	1	0
Autoimmune Thyroiditis [description not available]	2	1	0
Intestinal Perforation Opening or penetration through the wall of the INTESTINES.	2	1	0
Pancreatic Cyst A true cyst of the PANCREAS, distinguished from the much more common PANCREATIC PSEUDOCYST by possessing a lining of mucous EPITHELIUM. Pancreatic cysts are categorized as congenital, retention, neoplastic, parasitic, enterogenous, or dermoid. Congenital cysts occur more frequently as solitary cysts but may be multiple. Retention cysts are gross enlargements of PANCREATIC DUCTS secondary to ductal obstruction. (From Bockus Gastroenterology, 4th ed, p4145)	2	1	0
Dehydration The condition that results from excessive loss of water from a living organism.	2	1	0
Pyrexia [description not available]	2.37	2	0
Hypothermia, Accidental [description not available]	2.01	1	0
Fever An abnormal elevation of body temperature, usually as a result of a pathologic process.	2.37	2	0
Hypothermia Lower than normal body temperature, especially in warm-blooded animals.	2.01	1	0
Infections, Helicobacter [description not available]	2.41	2	0
Helicobacter Infections Infections with organisms of the genus HELICOBACTER, particularly, in humans, HELICOBACTER PYLORI. The clinical manifestations are focused in the stomach, usually the gastric mucosa and antrum, and the upper duodenum. This infection plays a major role in the pathogenesis of type B gastritis and peptic ulcer disease.	2.41	2	0
Infections, Vibrio [description not available]	2.01	1	0
Methemoglobinemia The presence of methemoglobin in the blood, resulting in cyanosis. A small amount of methemoglobin is present in the blood normally, but injury or toxic agents convert a larger proportion of hemoglobin into methemoglobin, which does not function reversibly as an oxygen carrier. Methemoglobinemia may be due to a defect in the enzyme NADH methemoglobin reductase (an autosomal recessive trait) or to an abnormality in hemoglobin M (an autosomal dominant trait). (Dorland, 27th ed)	2.01	1	0
Ganglioside Storage Diseases [description not available]	3.05	5	0
Lipidoses Conditions characterized by abnormal lipid deposition due to disturbance in lipid metabolism, such as hereditary diseases involving lysosomal enzymes required for lipid breakdown. They are classified either by the enzyme defect or by the type of lipid involved.	3.96	5	0
Gangliosidoses A group of autosomal recessive lysosomal storage disorders marked by the accumulation of GANGLIOSIDES. They are caused by impaired enzymes or defective cofactors required for normal ganglioside degradation in the LYSOSOMES. Gangliosidoses are classified by the specific ganglioside accumulated in the defective degradation pathway.	3.05	5	0
Bites [description not available]	2.86	1	0
Hypersensitivity, Type III [description not available]	2.86	1	0
Atelectasis [description not available]	1.95	1	0
Acid Aspiration Syndrome [description not available]	1.95	1	0
Pneumonia, Aspiration A type of lung inflammation resulting from the aspiration of food, liquid, or gastric contents into the upper RESPIRATORY TRACT.	1.95	1	0
Injuries Used with anatomic headings, animals, and sports for wounds and injuries. Excludes cell damage, for which pathology is used.	1.95	1	0
Wounds and Injuries Damage inflicted on the body as the direct or indirect result of an external force, with or without disruption of structural continuity.	1.95	1	0
ARSA Deficiency [description not available]	2.64	3	0
Leukodystrophy, Metachromatic An autosomal recessive metabolic disease caused by a deficiency of CEREBROSIDE-SULFATASE leading to intralysosomal accumulation of cerebroside sulfate (SULFOGLYCOSPHINGOLIPIDS) in the nervous system and other organs. Pathological features include diffuse demyelination, and metachromatically-staining granules in many cell types such as the GLIAL CELLS. There are several allelic and nonallelic forms with a variety of neurological symptoms.	2.64	3	0
Sphingolipid Storage Diseases [description not available]	2.35	2	0
Esophageal Varices [description not available]	1.95	1	0
Alcoholic Fatty Liver [description not available]	1.95	1	0
Esophageal and Gastric Varices Dilated blood vessels in the ESOPHAGUS or GASTRIC FUNDUS that shunt blood from the portal circulation (PORTAL SYSTEM) to the systemic venous circulation. Often they are observed in individuals with portal hypertension (HYPERTENSION, PORTAL).	1.95	1	0
Classic Globoid Cell Leukodystrophy [description not available]	3.21	6	0
Leukodystrophy, Globoid Cell An autosomal recessive metabolic disorder caused by a deficiency of GALACTOSYLCERAMIDASE leading to intralysosomal accumulation of galactolipids such as GALACTOSYLCERAMIDES and PSYCHOSINE. It is characterized by demyelination associated with large multinucleated globoid cells, predominantly involving the white matter of the central nervous system. The loss of MYELIN disrupts normal conduction of nerve impulses.	3.21	6	0
alpha-Galactosidase A Deficiency [description not available]	1.95	1	0
Fabry Disease An X-linked inherited metabolic disease caused by a deficiency of lysosomal ALPHA-GALACTOSIDASE A. It is characterized by intralysosomal accumulation of globotriaosylceramide and other GLYCOSPHINGOLIPIDS in blood vessels throughout the body leading to multi-system complications including renal, cardiac, cerebrovascular, and skin disorders.	1.95	1	0
Palsy [description not available]	1.95	1	0
Plant Poisoning Poisoning by the ingestion of plants or its leaves, berries, roots or stalks. The manifestations in both humans and animals vary in severity from mild to life threatening. In animals, especially domestic animals, it is usually the result of ingesting moldy or fermented forage.	1.95	1	0
Gall Bladder Diseases [description not available]	1.95	1	0
Paralysis A general term most often used to describe severe or complete loss of muscle strength due to motor system disease from the level of the cerebral cortex to the muscle fiber. This term may also occasionally refer to a loss of sensory function. (From Adams et al., Principles of Neurology, 6th ed, p45)	1.95	1	0
Anemia, Hemolytic, Acquired [description not available]	1.95	1	0
Anemia, Hemolytic A condition of inadequate circulating red blood cells (ANEMIA) or insufficient HEMOGLOBIN due to premature destruction of red blood cells (ERYTHROCYTES).	1.95	1	0
Hemoglobinuria The presence of free HEMOGLOBIN in the URINE, indicating hemolysis of ERYTHROCYTES within the vascular system. After saturating the hemoglobin-binding proteins (HAPTOGLOBINS), free hemoglobin begins to appear in the urine.	1.95	1	0
Hepatitis INFLAMMATION of the LIVER.	3.04	5	0
Disease A definite pathologic process with a characteristic set of signs and symptoms. It may affect the whole body or any of its parts, and its etiology, pathology, and prognosis may be known or unknown.	1.95	1	0
Dilatation, Pathologic The condition of an anatomical structure's being dilated beyond normal dimensions.	1.95	1	0
Celiac Sprue [description not available]	3.04	5	0
Celiac Disease A malabsorption syndrome that is precipitated by the ingestion of foods containing GLUTEN, such as wheat, rye, and barley. It is characterized by INFLAMMATION of the SMALL INTESTINE, loss of MICROVILLI structure, failed INTESTINAL ABSORPTION, and MALNUTRITION.	3.04	5	0
Deficiency, Vitamin A [description not available]	2.36	2	0
Vitamin A Deficiency A nutritional condition produced by a deficiency of VITAMIN A in the diet, characterized by NIGHT BLINDNESS and other ocular manifestations such as dryness of the conjunctiva and later of the cornea (XEROPHTHALMIA). Vitamin A deficiency is a very common problem worldwide, particularly in developing countries as a consequence of famine or shortages of vitamin A-rich foods. In the United States it is found among the urban poor, the elderly, alcoholics, and patients with malabsorption. (From Cecil Textbook of Medicine, 19th ed, p1179)	2.36	2	0
Blastomyces brasiliensis Infection [description not available]	1.95	1	0
Epulides, Giant Cell [description not available]	1.95	1	0
Blastomycosis, North American [description not available]	1.95	1	0
Blastomycosis A fungal infection that may appear in two forms: 1, a primary lesion characterized by the formation of a small cutaneous nodule and small nodules along the lymphatics that may heal within several months; and 2, chronic granulomatous lesions characterized by thick crusts, warty growths, and unusual vascularity and infection in the middle or upper lobes of the lung.	1.95	1	0
Granuloma, Giant Cell A non-neoplastic inflammatory lesion, usually of the jaw or gingiva, containing large, multinucleated cells. It includes reparative giant cell granuloma. Peripheral giant cell granuloma refers to the gingiva (giant cell epulis); central refers to the jaw.	1.95	1	0
ANS (Autonomic Nervous System) Diseases [description not available]	1.98	1	0
Choline Deficiency A condition produced by a deficiency of CHOLINE in animals. Choline is known as a lipotropic agent because it has been shown to promote the transport of excess fat from the liver under certain conditions in laboratory animals. Combined deficiency of choline (included in the B vitamin complex) and all other methyl group donors causes liver cirrhosis in some animals. Unlike compounds normally considered as vitamins, choline does not serve as a cofactor in enzymatic reactions. (From Saunders Dictionary & Encyclopedia of Laboratory Medicine and Technology, 1984)	2.89	4	0
Coronaviridae Infections Virus diseases caused by CORONAVIRIDAE.	1.97	1	0
Ileitis Inflammation of any segment of the ILEUM and the ILEOCECAL VALVE.	2.66	3	0
Infections, Plasmodium [description not available]	1.97	1	0
Malaria A protozoan disease caused in humans by four species of the PLASMODIUM genus: PLASMODIUM FALCIPARUM; PLASMODIUM VIVAX; PLASMODIUM OVALE; and PLASMODIUM MALARIAE; and transmitted by the bite of an infected female mosquito of the genus ANOPHELES. Malaria is endemic in parts of Asia, Africa, Central and South America, Oceania, and certain Caribbean islands. It is characterized by extreme exhaustion associated with paroxysms of high FEVER; SWEATING; shaking CHILLS; and ANEMIA. Malaria in ANIMALS is caused by other species of plasmodia.	1.97	1	0
Weight Reduction [description not available]	1.97	1	0
Weight Loss Decrease in existing BODY WEIGHT.	1.97	1	0
Morbid Obesity [description not available]	1.97	1	0
Obesity, Morbid The condition of weighing two, three, or more times the ideal weight, so called because it is associated with many serious and life-threatening disorders. In the BODY MASS INDEX, morbid obesity is defined as having a BMI greater than 40.0 kg/m2.	1.97	1	0
Central Hypothyroidism [description not available]	1.97	1	0
Hypothyroidism A syndrome that results from abnormally low secretion of THYROID HORMONES from the THYROID GLAND, leading to a decrease in BASAL METABOLIC RATE. In its most severe form, there is accumulation of MUCOPOLYSACCHARIDES in the SKIN and EDEMA, known as MYXEDEMA. It may be primary or secondary due to other pituitary disease, or hypothalamic dysfunction.	1.97	1	0
Urinary Fistula An abnormal passage in any part of the URINARY TRACT between itself or with other organs.	1.97	1	0
Ureteral Diseases Pathological processes involving the URETERS.	1.97	1	0
Deficiency, Vitamin E [description not available]	1.97	1	0
Pancreatic Fistula Abnormal passage communicating with the PANCREAS.	2.36	2	0
Duodenal Diseases Pathological conditions in the DUODENUM region of the small intestine (INTESTINE, SMALL).	1.96	1	0
Condition, Preneoplastic [description not available]	2.37	2	0
Precancerous Conditions Pathological conditions that tend eventually to become malignant.	2.37	2	0
Hemorrhage, Peptic Ulcer [description not available]	1.96	1	0
Xanthoma [description not available]	3.57	3	0
Intestinal Obstruction Any impairment, arrest, or reversal of the normal flow of INTESTINAL CONTENTS toward the ANAL CANAL.	2.36	2	0
Milk-Alkali Syndrome [description not available]	1.97	1	0
Hypercalcemia Abnormally high level of calcium in the blood.	1.97	1	0
Poultry Diseases Diseases of birds which are raised as a source of meat or eggs for human consumption and are usually found in barnyards, hatcheries, etc. The concept is differentiated from BIRD DISEASES which is for diseases of birds not considered poultry and usually found in zoos, parks, and the wild.	1.97	1	0
Ache [description not available]	1.97	1	0
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	1.97	1	0
MS (Multiple Sclerosis) [description not available]	1.96	1	0
Multiple Sclerosis An autoimmune disorder mainly affecting young adults and characterized by destruction of myelin in the central nervous system. Pathologic findings include multiple sharply demarcated areas of demyelination throughout the white matter of the central nervous system. Clinical manifestations include visual loss, extra-ocular movement disorders, paresthesias, loss of sensation, weakness, dysarthria, spasticity, ataxia, and bladder dysfunction. The usual pattern is one of recurrent attacks followed by partial recovery (see MULTIPLE SCLEROSIS, RELAPSING-REMITTING), but acute fulminating and chronic progressive forms (see MULTIPLE SCLEROSIS, CHRONIC PROGRESSIVE) also occur. (Adams et al., Principles of Neurology, 6th ed, p903)	1.96	1	0
Cacosmia [description not available]	1.96	1	0
Ulcer A lesion on the surface of the skin or a mucous surface, produced by the sloughing of inflammatory necrotic tissue.	1.96	1	0
Brain Disorders [description not available]	1.96	1	0
Brain Diseases Pathologic conditions affecting the BRAIN, which is composed of the intracranial components of the CENTRAL NERVOUS SYSTEM. This includes (but is not limited to) the CEREBRAL CORTEX; intracranial white matter; BASAL GANGLIA; THALAMUS; HYPOTHALAMUS; BRAIN STEM; and CEREBELLUM.	1.96	1	0
Hypernatremia Excessive amount of sodium in the blood. (Dorland, 27th ed)	1.96	1	0
Hyperthyroid [description not available]	2.86	1	0
Hyperthyroidism Hypersecretion of THYROID HORMONES from the THYROID GLAND. Elevated levels of thyroid hormones increase BASAL METABOLIC RATE.	2.86	1	0
Glycosuria The appearance of an abnormally large amount of GLUCOSE in the urine, such as more than 500 mg/day in adults. It can be due to HYPERGLYCEMIA or genetic defects in renal reabsorption (RENAL GLYCOSURIA).	1.95	1	0
Bacterial Overgrowth Syndrome [description not available]	1.95	1	0
Hepatitis, Infectious [description not available]	1.95	1	0
Hepatitis A INFLAMMATION of the LIVER in humans caused by a member of the HEPATOVIRUS genus, HUMAN HEPATITIS A VIRUS. It can be transmitted through fecal contamination of food or water.	1.95	1	0
Cystic Echinococcosis [description not available]	2.86	1	0
Trichostrongyloidiasis Infection by roundworms of the superfamily TRICHOSTRONGYLOIDEA, including the genera TRICHOSTRONGYLUS; OSTERTAGIA; Cooperia, HAEMONCHUS; Nematodirus, Hyostrongylus, and DICTYOCAULUS.	1.94	1	0
Salivary Gland Diseases Diseases involving the SALIVARY GLANDS.	1.94	1	0
Carcinoma, Anaplastic [description not available]	1.95	1	0
Carcinoma A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.	1.95	1	0
Besnoitiasis [description not available]	1.95	1	0
Alpers Diffuse Degeneration of Cerebral Gray Matter with Hepatic Cirrhosis [description not available]	1.95	1	0
Deficiency Diseases A condition produced by dietary or metabolic deficiency. The term includes all diseases caused by an insufficient supply of essential nutrients, i.e., protein (or amino acids), vitamins, and minerals. It also includes an inadequacy of calories. (From Dorland, 27th ed; Stedman, 25th ed)	1.95	1	0
Helminthiasis, Animal Infestation of animals with parasitic worms of the helminth class. The infestation may be experimental or veterinary.	1.95	1	0

taurocholic acid

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