cyclopentane profile

Cyclopentane is a cyclic alkane with the molecular formula C5H10. It is a colorless, flammable liquid with a mild, petroleum-like odor. It is found in natural gas and petroleum. Cyclopentane is used as a blowing agent for polystyrene foam, as a solvent in the pharmaceutical industry, and as a refrigerant. Cyclopentane is also a precursor to other chemicals, such as cyclopentanone and cyclopentanol. Cyclopentane is a relatively unreactive compound, but it can be oxidized to cyclopentanone or cyclopentanol. It is also susceptible to halogenation reactions. Cyclopentane is studied because it is a simple, yet important, cyclic molecule that provides insight into the properties of cyclic hydrocarbons. It is also a model system for studying the conformations of rings. '

Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

cyclopentanes : Cyclopentane and its derivatives formed by substitution. [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	9253
CHEMBL ID	1370850
CHEBI ID	23492
MeSH ID	M0005478

Synonym
un1146
hsdb 62
nsc 60213
einecs 206-016-6
pentamethylene
nsc60213
wln: l5tj
nsc-60213
ciclopentano
zyklopentan
cyclopentan
CHEBI:23492 ,
inchi=1/c5h10/c1-2-4-5-3-1/h1-5h
cyclopentane ,
287-92-3
NCGC00091776-01
68476-56-2
cyclopentanes
NCGC00091776-02
CHEMBL1370850
cas-287-92-3
NCGC00257756-01
tox21_200202
dtxsid6024886 ,
dtxcid804886
einecs 270-696-0
t86pb90rnu ,
unii-t86pb90rnu
ec 206-016-6
cyclopentane [un1146] [flammable liquid]
FT-0624250
AKOS015903084
cyclopentane [mi]
cyclopentane [hsdb]
un 1146
cyclopentane, hplc grade
mfcd00001356
cyclopentane, >=75% cyclopentane basis, spectrophotometric grade
cyclopentane, reagent grade, 98%
cyclopentane, analytical standard
cyclopentane, for hplc, >=75% cyclopentane basis
Q80260
PS-11988
blowing agent cyclopentane
95% cyclopentane
refrigerant cyclopentane
high purity cyclopentane
99% cyclopentane
solvent cyclopentane
foaming agent cyclopentane
trans-cyclopentane
cyclopentane (zeonsolvaa? hp)
astm method d5191 vapor pressure - 68.3kpa (9.91 psi)

Excerpt	Reference	Relevance
"The cyclopentane has been introduced with a totally controlled cis configuration, either into the middle of the aliphatic chain or at three methylene groups from the glycerol unit linked to the bulkier disaccharide residue."	( Synthesis and supramolecular assemblies of bipolar archaeal glycolipid analogues containing a cis-1,3-disubstituted cyclopentane ring. Benvegnu, T; Brard, M; Plusquellec, D; Richter, W, 2004)	1.01

Excerpt	Reference	Relevance
" They were given individually to guinea pigs prior to poisoning with 2 x LD50 soman to test their efficacy against organophosphorus-induced convulsions, brain damage, and lethality."	( Prevention of soman neurotoxicity by non-opioid antitussives. Braitman, DJ; Brennecke, LH; Sparenborg, S, 1990)	0.28
"We used an in-vitro, inhibition of protein synthesis assay (PSI) to test a wide variety of drugs for possible therapeutic use against ricin, a toxic glycoprotein that causes death in animals by inhibiting protein synthesis."	( Drugs that show protective effects from ricin toxicity in in vitro protein synthesis assays. Pace, JG; Scovill, JP; Thompson, WL, 1995)	0.29
" The presence of Hsp70 is thought to protect the cell against the toxic effects of the modified lipoprotein."	( Preconditioning of human smooth muscle cells via cyclopentenone prostaglandins protects against toxic effects of oxidized low-density lipoprotein. Clark, K; Hamel, L; Kenney, M; Merkel, L; Rojas, C, 2000)	0.31
" Since P-450 catalyzed oxidation of benzene is crucial to its toxic effects, the action of DAMC and related analogues were considered promising in preventing the genotoxicity due to benzene."	( Chemoprevention of benzene-induced bone marrow and pulmonary genotoxicity. Adhikari, JS; Bose, M; Dwarakanath, BS; Jain, SC; Kohli, E; Malik, S; Olsen, CE; Parmar, VS; Raj, HG; Rohil, V; Tyagi, YK, 2001)	0.31
" The absolute toxic dose was 50 mg/kg/day and the level at which no adverse effects were observed was 2 mg/kg/day for male and female dogs."	( Subacute toxicity and toxicokinetics of CJ-10882, a type IV phosphodiesterase inhibitor, after 4-week repeated oral administration in dogs. Han, J; Kim, B; Kim, JC; Shin, HC, 2004)	0.32
" Overall, the data obtained here suggest that positive modulation of GABAB receptors may serve as a novel therapeutic strategy for the development of anxiolytics, with a superior side effect profile to both baclofen and benzodiazepines."	( Behavioral characterization of the novel GABAB receptor-positive modulator GS39783 (N,N'-dicyclopentyl-2-methylsulfanyl-5-nitro-pyrimidine-4,6-diamine): anxiolytic-like activity without side effects associated with baclofen or benzodiazepines. Bettler, B; Chaperon, F; Cryan, JF; Froestl, W; Gentsch, C; Kaupmann, K; Kelly, PH; Lingenhoehl, K; Mombereau, C; Spooren, WP, 2004)	0.32
" With the exception of treatment-unrelated abnormality in surface righting reflex in the F1 generation, penequine hydrochloride did not produce any adverse effects at doses up to and including 12."	( The pre- and post-natal toxicity of penequine hydrochloride in mice. Huang, C; Jin, H; Wang, A; Wang, Z; Zhang, Q; Zhang, Z, 2006)	0.33
" Under the experimental conditions, penequine hydrochloride did not produce any adverse effects (expect the decreases in certain relative organ weights) up to and including 12."	( Fertility and early embryonic development toxicity of penequine hydrochloride in mice. Huang, C; Jin, H; Wang, A; Wang, Z; Zhang, Q; Zhang, Z, 2007)	0.34
" Finally, strong data exist to suggest that NG440 is a safe formula for human consumption."	( Clinical safety and efficacy of NG440: a novel combination of rho iso-alpha acids from hops, rosemary, and oleanolic acid for inflammatory conditions. Bland, JS; Carroll, B; Darland, G; Hall, A; Katke, J; Lamb, J; Lerman, RH; Minich, DM; Tripp, M, 2007)	0.34
" No serious adverse events were reported."	( Efficacy and safety of intravenous peramivir for treatment of seasonal influenza virus infection. Kida, H; Kohno, S; Mizuguchi, M; Shimada, J, 2010)	0.36
" In the present study, squalene production was achieved in a wild-type laboratory Saccharomyces cerevisiae strain by two safe chemical means using terbinafine (0."	( Enhanced squalene production by wild-type Saccharomyces cerevisiae strains using safe chemical means. Mantzouridou, F; Naziri, E; Tsimidou, MZ, 2011)	0.37
" The results of the safety evaluation among 117 patients enrolled in this study showed that adverse events and adverse drug reactions were reported in 62."	( Efficacy, safety, and pharmacokinetics of intravenous peramivir in children with 2009 pandemic H1N1 influenza A virus infection. Ishibashi, T; Kohno, S; Sugaya, N; Takahashi, T; Wajima, T, 2012)	0.38
" The EUA required healthcare providers to report medication errors, selected adverse events (AEs), serious AEs, and deaths to the FDA."	( Emergency use authorization for intravenous peramivir: evaluation of safety in the treatment of hospitalized patients infected with 2009 H1N1 influenza A virus. Birnkrant, D; Boucher, R; Camilli, S; Carter, W; Chan, I; Dal Pan, G; Dallas, S; Francis, H; Gada, N; Goodman, J; Jones, SC; Kosko, R; Scales, T; Sorbello, A; Struble, K; Thompson, E; Truffa, M, 2012)	0.38
"An FDA safety team analyzed reports submitted to the Adverse Event Reporting System (AERS) and sought follow-up in selected cases."	( Emergency use authorization for intravenous peramivir: evaluation of safety in the treatment of hospitalized patients infected with 2009 H1N1 influenza A virus. Birnkrant, D; Boucher, R; Camilli, S; Carter, W; Chan, I; Dal Pan, G; Dallas, S; Francis, H; Gada, N; Goodman, J; Jones, SC; Kosko, R; Scales, T; Sorbello, A; Struble, K; Thompson, E; Truffa, M, 2012)	0.38
" The safety data were insufficient to assess whether peramivir affected outcome or caused adverse reactions other than rash."	( Emergency use authorization for intravenous peramivir: evaluation of safety in the treatment of hospitalized patients infected with 2009 H1N1 influenza A virus. Birnkrant, D; Boucher, R; Camilli, S; Carter, W; Chan, I; Dal Pan, G; Dallas, S; Francis, H; Gada, N; Goodman, J; Jones, SC; Kosko, R; Scales, T; Sorbello, A; Struble, K; Thompson, E; Truffa, M, 2012)	0.38
" Peramivir was generally safe and well-tolerated with types and rates of adverse event similar to placebo."	( Single dose peramivir for the treatment of acute seasonal influenza: integrated analysis of efficacy and safety from two placebo-controlled trials. Alexander, WJ; Carson, S; Collis, P; Dobo, S; Elder, J; Laughlin, A; Mitha, E; Sheridan, WP; Stich, M; Tellier, G; Whitley, R, 2015)	0.42
" In total, 245 adverse events were observed with an incidence rate of 14."	( Post-marketing safety and effectiveness evaluation of the intravenous anti-influenza neuraminidase inhibitor peramivir. II: a pediatric drug use investigation. Ariyasu, Y; Ishii, S; Itoh, Y; Komeda, T; Sanekata, M; Shimada, J; Yoshikawa, T, 2015)	0.42
" In total, 412 adverse events were observed in 219 patients (28."	( Post-marketing safety evaluation of the intravenous anti-influenza neuraminidase inhibitor peramivir: A drug-use investigation in patients with high risk factors. Ishii, S; Itoh, Y; Komeda, T; Sanekata, M; Shimada, J; Yoshikawa, T, 2016)	0.43
"8%) experienced adverse events, all tolerated."	( Safety and efficacy of anti-influenza drugs, intravenous peramivir against influenza virus infection in elderly patients with underlying disease. Fukui, M; Hata, A; Marumo, S; Takamatsu, K, 2017)	0.46
"Transgenic mustard plants ( Brassica juncea ) expressing non-allergenic and biologically safe RiD peptide show higher tolerance against Lipaphis erysimi."	( Overexpression of biologically safe Rorippa indica defensin enhances aphid tolerance in Brassica juncea. Jana, K; Sarkar, P; Sikdar, SR, 2017)	0.46
" All adverse events (AEs) that occurred within 7 days after administration of peramivir were checked."	( Safety and Effectiveness of Peramivir in Korean Adult Influenza Patients: Prospective Observational Study Based on Post-Marketing Surveillance Data. Cheong, HJ; Choi, WS; Chung, DR; Chung, JW; Eom, JS; Hong, SB; Kim, DK; Kim, PY; Kim, SW; Kim, WJ; Lee, J; Lee, SR; Noh, JY; Ohk, T; Park, KH; Ryu, SY; Shin, J; Song, JY, 2018)	0.48
"Under the experimental conditions of this study, TM85 is less toxic than cisplatin, induces similar tumour reduction and avoids the formation of metastatic foci."	( Antitumour and Toxicity Evaluation of a Ru(II)-Cyclopentadienyl Complex in a Prostate Cancer Model by Imaging Tools. Gano, L; Garcia, MH; Gonçalves, MS; Jorge, TF; Marques, F; Martins, M; Matos, AP; Morais, TS; Pinheiro, T; Tomaz, AI; Tortosa, F; Valente, A, 2019)	0.51
" However, Si and MeJA applied alone or in combination significantly ameliorated the above-mentioned adverse effects induced by Cd."	( Effect of exogenous silicon and methyl jasmonate on the alleviation of cadmium-induced phytotoxicity in tomato plants. Guo, J; Hua, L; Li, H; Li, X; Ren, X; Sun, Y; Wei, T; Yashir, N, 2021)	0.62
"Aluminium (Al) is one of the most abundant metals in earth crust, which becomes toxic to the plants growing in acidic soil."	( Phytohormone signalling and cross-talk to alleviate aluminium toxicity in plants. Bishi, SK; Lal, SK; Ranjan, A; Singh, AK; Sinha, R, 2021)	0.62

Excerpt	Reference	Relevance
"The pharmacodynamic actions of (S)-2-[4,5-dihydro-5-propyl-2(3H)-furylidene]-1,3-cyclopentanedione (oudenone) were studied in both anesthetized animals and isolated organs."	( Pharmacodynamic actions of (S)-2-[4,5-dihydro-5-propyl-2-(3H)-furylidene]-1,3-cyclopentanedione (oudenone). Koide, T; Ozawa, H, 1976)	0.71
" The pharmacodynamic data, mean log viral titers, were described with the use of an empirical equation relating the viral growth and the effect of drug on changes in viral titers."	( Population analysis of the pharmacokinetics and pharmacodynamics of RWJ-270201 (BCX-1812) in treating experimental influenza A and B virus in healthy volunteers. Iyer, GR; Liao, S; Massarella, J, 2002)	0.31
"Pharmacokinetic analyses show that weight was the most significant covariate for all estimated pharmacokinetic parameters."	( Population analysis of the pharmacokinetics and pharmacodynamics of RWJ-270201 (BCX-1812) in treating experimental influenza A and B virus in healthy volunteers. Iyer, GR; Liao, S; Massarella, J, 2002)	0.31
" The method has been successfully applied to a pharmacokinetic study of Ginkgo biloba extract in rats after intravenous administration."	( Simultaneous determination of ginkgolides A, B, C and bilobalide in plasma by LC-MS/MS and its application to the pharmacokinetic study of Ginkgo biloba extract in rats. Ding, C; Ge, Q; Xie, J; Zhi, X; Zhou, Z, 2008)	0.35
" Noncompartmental pharmacokinetic parameters were determined from plasma and urine concentration-time data."	( Effect of renal impairment on the pharmacokinetics of PD 0200390, a novel ligand for the voltage-gated calcium channel alpha-2-delta subunit. Corrigan, B; Feltner, DE; Gibson, G; Moton, AE; Ouellet, D; Werth, JL, 2009)	0.35
"PD 0200390 pharmacokinetic parameters (CL/F, CL(R) and AUC(0-infinity)) vary predictably with decreases in renal function; therefore dose adjustment may be required in individuals with RI."	( Effect of renal impairment on the pharmacokinetics of PD 0200390, a novel ligand for the voltage-gated calcium channel alpha-2-delta subunit. Corrigan, B; Feltner, DE; Gibson, G; Moton, AE; Ouellet, D; Werth, JL, 2009)	0.35
"This pharmacokinetic (PK) study was designed to characterize the dose response of two concentrations (0."	( Comparison pharmacokinetics of two concentrations (0.7% and 1.0%) of Nasulin, an ultra-rapid-acting intranasal insulin formulation. Marbury, T; Miller, M; Shi, L; Stote, R; Strange, P, 2010)	0.36
" Glucose AUC((0-45 min)) determinations also demonstrated a pharmacodynamic (PD) dose response."	( Comparison pharmacokinetics of two concentrations (0.7% and 1.0%) of Nasulin, an ultra-rapid-acting intranasal insulin formulation. Marbury, T; Miller, M; Shi, L; Stote, R; Strange, P, 2010)	0.36
" Two additional postinfusion concentrations were measured from each patient to estimate noncompartmental pharmacokinetic parameters of peramivir while receiving CVVHDF."	( Peramivir pharmacokinetics in two critically ill adults with 2009 H1N1 influenza A concurrently receiving continuous renal replacement therapy. Bauer, KA; Bazan, JA; Firstenberg, MS; Goff, DA; Hollister, AS; Mangino, JE; Reed, EE; Shidham, G, 2010)	0.36
" Additional pharmacokinetic data are needed to confirm these results and help guide dosing in patients receiving various forms of CRRT."	( Peramivir pharmacokinetics in two critically ill adults with 2009 H1N1 influenza A concurrently receiving continuous renal replacement therapy. Bauer, KA; Bazan, JA; Firstenberg, MS; Goff, DA; Hollister, AS; Mangino, JE; Reed, EE; Shidham, G, 2010)	0.36
"The pharmacokinetic parameters in this patient were unexpected because the clearances occurred more quickly than in phase I trials."	( Postpartum pharmacokinetics of peramivir in the treatment of 2009 H1N1 influenza. Adiga, RB; Alsup, R; Clay, PG; Gerk, PM; McRae, M; Taylor, TAH, 2011)	0.37
" Two studies were conducted to assess the potential for pharmacokinetic interactions of peramivir when coadministered with oseltamivir or rimantadine."	( Absence of pharmacokinetic interaction between intravenous peramivir and oral oseltamivir or rimantadine in humans. Atiee, G; Baughman, S; Collis, P; Hernandez, J; Hollister, A; Lasseter, K; McCullough, A, 2012)	0.38
" A population pharmacokinetic analysis was performed on the basis of 297 observed plasma concentration data obtained from 115 children with influenza virus infection."	( Efficacy, safety, and pharmacokinetics of intravenous peramivir in children with 2009 pandemic H1N1 influenza A virus infection. Ishibashi, T; Kohno, S; Sugaya, N; Takahashi, T; Wajima, T, 2012)	0.38
"The purpose of this study was to investigate the relationship between pharmacokinetic (PK) parameters of intravenous (IV) peramivir and in vivo antiviral activity pharmacodynamic (PD) outcomes in a mouse model of influenza virus infection."	( The relationship between in vivo antiviral activity and pharmacokinetic parameters of peramivir in influenza virus infection model in mice. Baba, K; Hasegawa, T; Homma, T; Izawa, M; Kamimori, H; Kanazu, T; Kida, H; Kitano, M; Kobayashi, M; Kodama, M; Noshi, T; Okazaki, K; Sakoda, Y; Sato, A; Seki, T; Tsuji, M; Yamano, Y; Yoshida, R, 2014)	0.4
" doses of 300 and 600 mg peramivir, Cmax and AUC0-t of peramivir were 21."	( Pharmacokinetics of peramivir after single intravenous doses in healthy Chinese subjects. Deng, M; Du, A; Liu, H; Ma, J; Meng, L; Xu, J; Zhang, D; Zhang, L, 2015)	0.42
" This case report provides data on the dialysis membrane saturation coefficient (SA) and pharmacokinetic parameters of peramivir in a 29-year-old female receiving continuous veno-venous hemodiafiltration (CVVHDF), a mode of CRRT."	( Peramivir pharmacokinetics in a patient receiving continuous veno-venous hemodiafiltration during the 2009 H1N1 influenza A pandemic. Bentley, ML; Cain, JS; Hansenb, AC; Hollistera, AS; Smith, JA, 2014)	0.4
" The maximum and minimum plasma concentrations, AUC0-24, and plasma half-life was similar to those previously reported."	( Peramivir pharmacokinetics in a patient receiving continuous veno-venous hemodiafiltration during the 2009 H1N1 influenza A pandemic. Bentley, ML; Cain, JS; Hansenb, AC; Hollistera, AS; Smith, JA, 2014)	0.4
" To characterize its pharmacokinetics, a population pharmacokinetic analysis of peramivir was performed using 3,199 plasma concentration data samples from 332 subjects in six clinical studies in Japan and the United States, including studies with renal impairment subjects, elderly subjects, and influenza patients."	( Population pharmacokinetics of peramivir in healthy volunteers and influenza patients. Hollister, AS; Ishibashi, T; Matsuo, Y; Wajima, T, 2015)	0.42
" The population pharmacokinetic model developed for peramivir should be useful for understanding its pharmacokinetic characteristics and for dose adjustment on the basis of renal function."	( Population pharmacokinetics of peramivir in healthy volunteers and influenza patients. Hollister, AS; Ishibashi, T; Matsuo, Y; Wajima, T, 2015)	0.42
" Baclofen is known to produce anticonvulsant effects in the DBA/2J mouse audiogenic seizure test (AGS), suggesting it may be a suitable assay for assessing pharmacodynamic effects."	( Anticonvulsant effects of structurally diverse GABA(B) positive allosteric modulators in the DBA/2J audiogenic seizure test: Comparison to baclofen and utility as a pharmacodynamic screening model. Brown, JW; Ma, J; Moeller, A; Nimmrich, V; Rueter, LE; Schmidt, M; Turner, SC; van der Kam, E; Zhang, M, 2016)	0.43
"The pharmacokinetic properties obtained here for intravenous peramivir are consistent with the previously reported clinical efficacy and safety of this antiviral."	( Pharmacokinetics and safety of intravenous peramivir, neuraminidase inhibitor of influenza virus, in healthy Japanese subjects. Fukase, H; Fukuyama, H; Ishibashi, T; Saisho, Y; Shimada, J, 2017)	0.46
"To estabish ultra-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) method for simultaneous determination of quercetin(QCT), isorhamnetin(ISR), kaempferol(KMF), ginkgolide A(GA), ginkgolide B(GB), ginkgolide C(GC) and bilobalide(BB) in rat plasma and investigate the pharmacokinetic process of seven compounds after oral administration of Yindan Xinnaotong Ruanjiaonang, The results indicated that all calibrations curves showed good linearity (r≥0."	( [Simultaneous determination of seven bioactive compounds and pharmacokinetics in rat plasma after oral administration of Yindan Xinnaotong Ruanjiaonang by UPLC-MS/MS]. Gong, LL; Liang, RX; Wang, L; Xu, HY; Yang, HJ; Yin, XJ; Yuan, HJ, 2017)	0.46
"A population pharmacokinetic (PK) analysis was conducted to quantify the impact of patient-specific and concurrent medication factors on pevonedistat PK."	( Population pharmacokinetics of pevonedistat alone or in combination with standard of care in patients with solid tumours or haematological malignancies. Faessel, HM; Faller, DV; Mould, DR; Sedarati, F; Venkatakrishnan, K; Zhou, X, 2019)	0.51
" Ten (91%) patients demonstrated a larger volume of distribution, 11 (100%) patients demonstrated an increase in clearance, and 11 (100%) patients demonstrated a shorter half-life estimate as compared with the package insert and previous pediatric trial data for peramivir."	( Peramivir for Influenza A and B Viral Infections: A Pharmacokinetic Case Series. Chopra, A; Cies, JJ; Enache, A; Moore, WS, 2019)	0.51
"The pharmacokinetics of PRV demonstrated in this PICU cohort differs in comparison to healthy pediatric and adult patients, and alterations to dosing regimens may be needed in PICU patients to achieve pharmacodynamic exposures."	( Peramivir for Influenza A and B Viral Infections: A Pharmacokinetic Case Series. Chopra, A; Cies, JJ; Enache, A; Moore, WS, 2019)	0.51
" Pharmacokinetic studies indicated that bilobalide may have the characteristics of rapid absorption, good bioavailability, wide distribution, and slow elimination."	( Bilobalide: A review of its pharmacology, pharmacokinetics, toxicity, and safety. Cao, Y; Dai, X; Li, X; Liang, Y; Liu, K; Lu, J; Wang, X; Xie, L; Zhang, X, 2021)	0.62

Excerpt	Reference	Relevance
"An efficient system to produce saikosaponins (saikosaponin-a and -d) in Bupleurum falcatum adventitious root fragments combined with signal transducers was developed."	( Efficient production of saikosaponins in Bupleurum falcatum root fragments combined with signal transducers. Aoyagi, H; Kobayashi, Y; Kusakari, K; Tanaka, H; Yamada, K; Yokoyama, M, 2001)	0.31
"Static headspace sampling with solid-phase microextraction has been used in combination with GC-FID and GC-MS for the specific enrichment, identification and quantification of volatile methyl jasmonate secreted by wounded leaves of Arabidopsis thaliana."	( Identification and quantification of methyl jasmonate in leaf volatiles of Arabidopsis thaliana using solid-phase microextraction in combination with gas chromatography and mass spectrometry. Dubery, IA; Meyer, R; Rautenbach, GF, )	0.13
" The data suggest that KI-063 has an additive effect in combination with terrein."	( The hypopigmentary action of KI-063 (a new tyrosinase inhibitor) combined with terrein. Baek, KJ; Kim, DS; Kwon, SB; Lee, HK; Lee, S; Na, JI; Park, KC; Park, SH; Ryoo, IJ; Yoo, ID, 2008)	0.35
" We studied the effects of methyl jasmonate in combination with sucrose on defense-related gene expression, stilbene and anthocyanin production in grapevine cell suspensions."	( Effect of methyl jasmonate in combination with carbohydrates on gene expression of PR proteins, stilbene and anthocyanin accumulation in grapevine cell cultures. Barrieu, F; Belhadj, A; Cluzet, S; Hamdi, S; Mérillon, JM; Saigne, C; Telef, N, 2008)	0.35
"The effects of methyl jasmonate (MeJA) in combination with ethanol (EtOH) treatment on green mold rot caused by Penicillium citrinum , natural decay, and antioxidant capacity in harvested Chinese bayberries were investigated."	( Effect of methyl jasmonate in combination with ethanol treatment on postharvest decay and antioxidant capacity in Chinese bayberries. Jin, P; Shang, H; Wang, K; Zheng, Y, 2010)	0.36
" However, when levetiracetam (LEV; 50mg/kg) was combined with either procyclidine (PCD; 10mg/kg) or caramiphen (CMP; 10mg/kg) complete cessation of seizures was achieved, but the nicotinic antagonist mecamylamine was needed to induce full motor rest in some rats."	( Enhanced efficacy of anticonvulsants when combined with levetiracetam in soman-exposed rats. Aas, P; Enger, S; Jonassen, M; Myhrer, T, 2011)	0.37
"To investigate the effect of Eucommiol on osteogenic differentiation of adipose-derived stem cells (ADSCs), and the feasibility of applying in mandibular defects repair using ADSCs combined with the extract of Eucommiol scaffold material."	( [Research on the adipose-derived stem cells combined with the extract of Eucommiol scaffold material to repair the rabbit mandible defect]. Fang, D; Guo, Y; Li, S; Ning, Z, 2013)	0.39
" Group A: Implanted the ADSCs combined with the extract of Eucommiol scaffold, group B: Implanted the ADSCs combined with hydroxyapatite materials, group C: Implanted hydroxyapatite materials, group D: The control group."	( [Research on the adipose-derived stem cells combined with the extract of Eucommiol scaffold material to repair the rabbit mandible defect]. Fang, D; Guo, Y; Li, S; Ning, Z, 2013)	0.39
" The role of ADSCs combined with extract of Eucommiol scaffold materials has significant bone induction."	( [Research on the adipose-derived stem cells combined with the extract of Eucommiol scaffold material to repair the rabbit mandible defect]. Fang, D; Guo, Y; Li, S; Ning, Z, 2013)	0.39
" In the reported study we aimed to provide evidence for this assumption and investigated the drug combination of cisplatin and the neddylation inhibitor MLN4924 in HCT-116 cells via cell biological analyses and mass spectrometry-based quantitative proteomics."	( Systematic analysis of synergistic proteome modulations in a drug combination of cisplatin and MLN4924. Abou-Eid, S; Megger, DA; Sitek, B; Zülch, B, 2018)	0.48
"Data were pooled from 6 clinical studies consisting of 335 patients with solid tumours or haematological malignancies administered pevonedistat alone or in combination with azacitidine, docetaxel, carboplatin + paclitaxel, or gemcitabine."	( Population pharmacokinetics of pevonedistat alone or in combination with standard of care in patients with solid tumours or haematological malignancies. Faessel, HM; Faller, DV; Mould, DR; Sedarati, F; Venkatakrishnan, K; Zhou, X, 2019)	0.51

Excerpt	Reference	Relevance
"The bioavailability of ginkgolides A, B and bilobalide was studied in rats after single oral administration of 30, 55 and 100 mg/kg Ginkgo extract EGb 761."	( Bioavailability of ginkgolides and bilobalide from extracts of ginkgo biloba using GC/MS. Biber, A; Koch, E, 1999)	0.3
" Both exhibit good oral bioavailability and are potent in standard models of pain, fever, and inflammation yet have a much reduced effect on the GI integrity of rats compared to standard nonsteroidal antiflammatory drugs."	( 2,3-Diarylcyclopentenones as orally active, highly selective cyclooxygenase-2 inhibitors. Black, WC; Brideau, C; Chan, CC; Charleson, S; Chauret, N; Claveau, D; Ethier, D; Gordon, R; Greig, G; Guay, J; Hughes, G; Jolicoeur, P; Leblanc, Y; Nicoll-Griffith, D; Ouimet, N; Prasit, P; Riendeau, D; Visco, D; Wang, Z; Xu, L, 1999)	0.3
" With respect to the relevance of biopharmaceutical quality of herbal medicinal products, two different Ginkgo biloba brands (test product: Ginkgo biloba capsules; reference product: Ginkgold) were analysed for dissolution rates and bioavailability of the most relevant active ingredients."	( Influence of pharmaceutical quality on the bioavailability of active components from Ginkgo biloba preparations. Biber, A; Blume, HH; Kressmann, S; Müller, WE; Schug, B; Wonnemann, M, 2002)	0.31
" Across all schedules, CGP7930 was more effective at decreasing cocaine self-administration than GS39783, a finding that may be due to differences in bioavailability between the two drugs."	( Effects of positive allosteric modulators of the GABAB receptor on cocaine self-administration in rats. Froestl, W; Liu, Y; Morgan, D; Roberts, DC; Smith, MA; Yancey, DL, 2004)	0.32
" Recent articles reported that curcumin's instability and low bioavailability in vivo are mainly due to its easily decomposable beta-diketone moiety."	( Synthesis, structure, and bioevaluation of 2,5-bis(arylmethenyl)cyclopentanones. Li, XK; Liang, G; Lv, YX; Shao, LL; Xiao, J; Yang, J; Yang, SL; Zhao, CG; Zhao, Y, )	0.13
" We also investigated its bioavailability in humans and its anti-inflammatory effect ex vivo."	( META060 inhibits multiple kinases in the NF-kappaB pathway and suppresses LPS--mediated inflammation in vitro and ex vivo. Austin, M; Bland, JS; Carroll, BJ; Darland, G; Desai, A; Konda, VR; Prabhu, KS; Tripp, ML, 2009)	0.35
" Bioavailability was tested in 4 human subjects consuming 940 mg META060."	( META060 inhibits multiple kinases in the NF-kappaB pathway and suppresses LPS--mediated inflammation in vitro and ex vivo. Austin, M; Bland, JS; Carroll, BJ; Darland, G; Desai, A; Konda, VR; Prabhu, KS; Tripp, ML, 2009)	0.35
" The results of the present study clearly confirm the improvement of oral bioavailability of bilobalide administered as phospholipidic complex and, for the first time, demonstrate the detection of significative amounts of bilobalide in brain."	( Liquid chromatography/atmospheric pressure chemical ionization ion trap mass spectrometry of bilobalide in plasma and brain of rats after oral administration of its phospholipidic complex. Basilico, F; Mauri, PL; Morazzoni, P; Riva, A; Rossi, R; Rossoni, G, 2009)	0.35
" However, poor bioavailability greatly limits its application in clinic."	( A novel synthetic mono-carbonyl analogue of curcumin, A13, exhibits anti-inflammatory effects in vivo by inhibition of inflammatory mediators. Feng, Z; Huang, Y; Li, X; Liang, G; Pan, Y; Wang, Y; Yang, S; Yang, X; Yu, C, 2012)	0.38
" The most important pharmacokinetic parameters (C(max), t(max), half life, clearance, and AUC(0-∞)) and the absolute bioavailability were determined for each class of hop acid."	( Bioavailability of hop-derived iso-α-acids and reduced derivatives. Boussery, K; Bracke, M; Cattoor, K; De Keukeleire, D; Deforce, D; Heyerick, A; Remon, JP; Van Bocxlaer, J, 2011)	0.37
" Incorporation of a 1,2,4-oxadiazole linker and substitution of the pendant phenyl ring led to the discovery of orally bioavailable analogues that showed efficient NR2B receptor occupancy in rats."	( Discovery of 3-substituted aminocyclopentanes as potent and orally bioavailable NR2B subtype-selective NMDA antagonists. Bednar, RA; Cunningham, ME; Dilella, AG; Fandozzi, C; Fay, JF; Kelly, MJ; Koblan, KS; Layton, ME; Liang, A; Lis, EV; McDonald, TP; Mosser, SD; Reiss, DR; Rodzinak, KJ; Sanderson, PE; Seabrook, GR; Trainor, N; Urban, MO; Wang, H; Yergey, J; Young, SD, 2011)	0.65
" These systems are able to incorporate drugs modifying bioavailability and stability and reducing toxic effects."	( Development and characterization of biocompatible isotropic and anisotropic oil-in-water colloidal dispersions as a new delivery system for methyl dihydrojasmonate antitumor drug. da Silva, GB; de Oliveira, AG; do Egito, ES; Rossanezi, G; Scarpa, MV, 2014)	0.4
"Percutaneous absorption assays of molecules for pharmaceutical and cosmetology purposes are important to determine the bioavailability of new compounds, once topically applied."	( A Microfluidic Diffusion Cell for Fast and Easy Percutaneous Absorption Assays. Fujii, T; Grégoire, S; Nicolas, A; Provin, C, 2015)	0.42
"To investigate the pharmacokinetic characteristics and absolute bioavailability of ginkgolide A (GA), ginkgolide B (GB) and bilobalide (BB) in rats."	( [Absolute bioavailability of ginkgolide compounds in rats]. Geng, T; Si, HH; Sun, XP; Xue, J; Zhao, J, 2015)	0.42
" Terpene lactones are orally bioavailable and predominantly eliminated via the renal pathway."	( Influence of organic anion transporter 1/3 on the pharmacokinetics and renal excretion of ginkgolides and bilobalide. He, H; Nie, J; Wang, R; Xu, M; Yao, J; Yaro, P; Zeng, K; Zeng, S, 2019)	0.51

Excerpt	Relevance	Reference
" Fast absorpiton of the drug from the gastrointestinal tract was indicated by the rapid increase in plasma levels during the absorption phase, with a peak time at about 1 hour after dosing in all subjects."	( Plasma level studies of penbutolol after oral dose in man. Brown, W; Frazer, H; Honigberg, IL; Jun, HW; Needham, TE; Stewart, JT; Vallner, JJ, 1977)	0.26
" A dose-response relationship to intravenous doses of propranolol in the microgram range was obtained during a steady state of infusion of epinephrine."	( Beta-2 adrenoceptor blocking activity of penbutolol and propranolol at very low doses. Chabria, NL; Chadha, DR; DaSilva, LM; Kulkarni, RD, 1977)	0.26
" The dosage range for penbutolol was 8 mg to 50 mg per day."	( A double-blind trial of penbutolol: a new beta-receptor blocking agent in the treatment of angina pectoris. Agarwal, AK; Ahuja, RC; Chandra, M; Gupta, NN; Hasan, M, 1976)	0.26
" The dose of penbutolol producing an effect equivalent to that of propranolol was calculating from the log dose-response curve of penbutolol."	( Comparative potency of intravenous penbutolol and propranolol in man. Sapru, RP; Sharma, PL, 1978)	0.26
" The classification of the anti-androgens, their indications, side-effects, dosage schemes and results of treatment are reviewed."	( [Clinical aspects of the anti-androgens]. Holtzhausen, GH, 1979)	0.26
" The drug acted with a similar dose-response curve upon intact as well as detergent-dispersed cyclase preparations."	( RMI 12330 A, an inhibitor of adenylate cyclase in rat liver. Berthelot, P; Guellaen, G; Hanoune, J; Mahu, JL; Mavier, P, 1977)	0.26
" Cyclopentenone was dosed at a level of 18 ppm (seven hr/day, five days/week) during the first 52 weeks, and at a level of 27 ppm during the last 26 weeks of the study."	( Repeated exposure to cyclopentenone vapour: long-term study in Syrian golden hamsters. Feron, VJ; Kruysse, A, 1976)	0.26
" It is suggested that unless full dark adaptation is a consideration, treatment of the ophthalmic condition resulting from exposure to this dosage of sarin should be reserved for those experiencing distressing ocular symptoms."	( Cyclopentolate in treatment of sarin miosis. Moylan-Jones, RJ; Thomas, DP, 1973)	0.25
" This reverse dose-response may be due to the relatively high cytotoxicity of CPEP, BP, which was compared to CPEP at the low dose, elicited tumors in 100% of the mice."	( Carcinogenicity of the environmental pollutants cyclopenteno-[cd]pyrene and cyclopentano[cd]pyrene in mouse skin. Cavalieri, E; Munhall, A; Rogan, E; Toth, B, 1981)	0.26
" In the sodium-replete SHR, 5 days of oral dosing with pivalopril, 100 mg/(kg ."	( Angiotensin-converting enzyme inhibitory and antihypertensive activities of pivalopril (RHC 3659-(S)). Loev, B; Mann, WS; Smith, RD; Suh, JT; Wolf, PS, 1984)	0.27
" Dose-response studies demonstrated that the effects of BFA were half-maximal at a dose of 1 microgram/ml and maximal at about 10 micrograms/ml."	( Brefeldin A inhibits insulin-dependent receptor redistribution in HIRcB cells. Romero, G; Shome, K; Xu, XQ, 1995)	0.29
" The dose-response to JA parallels previous reports on alkaloid induction in cell cultures."	( Herbivore-induced volatiles: the emission of acyclic homoterpenes from leaves of Phaseolus lunatus and Zea mays can be triggered by a beta-glucosidase and jasmonic acid. Blechert, S; Boland, W; Donath, J; Hopke, J, 1994)	0.29
" When the y axes were scaled appropriately, the dose-response curves for collagen degradation +/- cis-hydroxyproline versus BFA concentration coincided."	( Brefeldin A inhibits degradation as well as production and secretion of collagen in human lung fibroblasts. Bienkowski, RS; Fant, J; Ripley, CR, 1993)	0.29
" Jasmonic acid addition caused an increase in the specific yields of ajmalicine (80%), serpentine (60%), lochnericine (150%), and hörhammericine (500%) in dosage studies."	( Effect of elicitor dosage and exposure time on biosynthesis of indole alkaloids by Catharanthus roseus hairy root cultures. Rijhwani, SK; Shanks, JV, )	0.13
"9-fold rightward shift of the cumulative dose-response curves."	( Clinically available NMDA receptor antagonists memantine and dextromethorphan reverse existing tolerance to the antinociceptive effects of morphine in mice. Danysz, W; Kozela, E; Popik, P, 2000)	0.31
" Quantitative dose-response relations were found between the increase in nectar production and both the intensity of leaf damage and the amounts of exogenously applied JA."	( Extrafloral nectar production of the ant-associated plant, Macaranga tanarius, is an induced, indirect, defensive response elicited by jasmonic acid. Boland, W; Fiala, B; Heil, M; Hilpert, A; Koch, T; Linsenmair, K, 2001)	0.31
" Oral administration of a dosage of 1 mg/kg of body weight/day of RWJ-270201 for 5 days (beginning 4 h preinfection) showed efficacy in the murine model of influenza virus infection as determined by lethality and weight loss protection."	( Comparison of the anti-influenza virus activity of RWJ-270201 with those of oseltamivir and zanamivir. Ananth, SL; Andries, K; Babu, YS; Bantia, S; Chand, P; Dehghani, A; El-Kattan, Y; Horn, LL; Hutchison, TL; Kellog, DL; Kotian, PL; Lin, T; Montgomery, JA; Parker, CD, 2001)	0.31
" The following metabolites were isolated and identified from the urine of rats dosed with I: 3-methyl-5-(1-methylethylidene)-cyclopent-2-enone (Ie), Z-4-methyl-2-(1-hydroxymethylethylidene)-cyclopentanone (Ib), E-4-methyl-2-(1-hydroxymethylethylidene)-cyclopentanone (Ia), 3-hydroxy-4-methyl-2-(1-methylethylidene)-cyclopentanone (If), 4-hydroxy-4-methyl-2-(1-methylethylidene)-cyclopentanone (Ic), and E-4-methyl-2-(1-carboxyethylidene)-cyclopentanone (Id)."	( Effect of ring size in R-(+)-pulegone-mediated hepatotoxicity: studies on the metabolism of R-(+)-4-methyl-2-(1-methylethylidene)-cyclopentanone and DL-camphorone in rats. Bhat, VB; Madyastha, MK; Thulasiram, HV, 2001)	0.31
" We conclude that once-daily dosing of RWJ-270201 should be evaluated in clinical trials of influenza therapy."	( Pharmacodynamic evaluation of RWJ-270201, a novel neuraminidase inhibitor, in a lethal murine model of influenza predicts efficacy for once-daily dosing. Bailey, K; Bush, K; Drusano, GL; Preston, SL; Sidwell, RW; Smee, D, 2001)	0.31
" A pharmacokinetic study of this compound in influenza virus-infected mice indicates once-, twice- or thrice-daily oral dosing was equal in efficacy; once-daily dosing has been recommended in clinical trials of influenza therapy."	( Peramivir (BCX-1812, RWJ-270201): potential new therapy for influenza. Sidwell, RW; Smee, DF, 2002)	0.31
" Both compounds, given intracerebroventricularly at doses which did not show marked anticonvulsant activity, produced a consistent shift to the left of the dose-response curves (i."	( Group III mGlu receptor agonists potentiate the anticonvulsant effect of AMPA and NMDA receptor block. Chimirri, A; De Sarro, G; Meldrum, BS, 2002)	0.31
" Corresponding dose-response relationships are close to single-site binding isotherms."	( Structure-activity studies with Ginkgo biloba extract constituents as receptor-gated chloride channel blockers and modulators. Chatterjee, SS; Kondratskaya, EL; Krishtal, OA, 2003)	0.32
" Therefore, whether a proper dosage of bilobalide is used or not plays a critical factor in deciding if it can sustain nerve regeneration over long gaps."	( Effect of bilobalide on peripheral nerve regeneration. Chen, YS; Cheng, CY; Liu, CJ; Yao, CH, 2004)	0.32
" They also received the experimental diets containing EGb (50 or 500 ppm) and bilobalide (15 or 150 ppm) for 4 weeks, starting 1 week before the first dosing of AOM."	( Preventive effects of extract of leaves of ginkgo (Ginkgo biloba) and its component bilobalide on azoxymethane-induced colonic aberrant crypt foci in rats. Kohno, H; Sasaki, K; Sugie, S; Suzuki, R; Tanaka, T; Wada, K; Yoshimura, T, 2004)	0.32
" Exogenous JA did not adversely affect productivity, and in the absence of drought stress, the higher dosage enhanced grain yield."	( The effect of exogenous jasmonic acid on induced resistance and productivity in amaranth (Amaranthus hypochondriacus) is influenced by environmental conditions. Barbosa-Jaramillo, ER; Borodanenko, A; Délano-Frier, JP; Martínez-de la Vega, O; Martínez-Gallardo, NA; Salas-Araiza, MD; Torres, A; Vargas, P, 2004)	0.32
" Commercially available authentic standards of the identified compounds were tested in dose-response studies on hamster oviducts."	( Phenols, quinolines, indoles, benzene, and 2-cyclopenten-1-ones are oviductal toxicants in cigarette smoke. Riveles, K; Roza, R; Talbot, P, 2005)	0.33
" arf6 and arf8 single mutants and sesquimutants (homozygous for one mutation and heterozygous for the other) had delayed stamen development and decreased fecundity, indicating that ARF6 and ARF8 gene dosage affects timing of flower maturation quantitatively."	( Auxin response factors ARF6 and ARF8 promote jasmonic acid production and flower maturation. Alonso, JM; Barkawi, LS; Cohen, JD; Ecker, JR; Ellis, CM; Farmer, EE; Guilfoyle, TJ; Hagen, G; Nagpal, P; Ploense, SE; Reed, JW; Weber, H, 2005)	0.33
" The results showed that methyl jasmonate and salicylic acid enhanced greatly the accumulation of PeG and echinacoside (Echin), but their optimum elicitation dosage and addition time were different."	( [Effects of methyl jasmonate and salicylic acid on phenylethanoid glycosides synthesis in suspension cultures of Cistanche deserticola]. Chen, YQ; Fu, CX; Jin, ZP; Xu, LS; Xue, XF; Zhao, DX, 2005)	0.33
" At low concentration, bilobalide (3 microM) caused a parallel right shift and surmountable GABA maximal response of the GABA dose-response curve characteristic of a competitive antagonist."	( Mixed antagonistic effects of bilobalide at rho1 GABAC receptor. Chebib, M; Duke, RK; Huang, SH; Johnston, GA; Sasaki, K; Wada, K, 2006)	0.33
"A reversed phase high performance liquid chromatographic method with evaporative light scattering detection (RP-HPLC-ELSD) was developed for the quantitative determination of the terpene trilactones, ginkgolide A, B, C and J and the sesquiterpene, bilobalide in Ginkgo biloba solid oral dosage forms."	( Determination of terpene trilactones in Ginkgo biloba solid oral dosage forms using HPLC with evaporative light scattering detection. Dubber, MJ; Kanfer, I, 2006)	0.33
"For treatment dosing was initiated at 24 h after inoculation with peramivir doses ranging from 100-800 mg/day for 5 days."	( Efficacy and tolerability of the oral neuraminidase inhibitor peramivir in experimental human influenza: randomized, controlled trials for prophylaxis and treatment. Barroso, L; Gubareva, L; Hayden, FG; Treanor, J, 2005)	0.33
" The relatively low blood peramivir concentrations observed may explain the lack of more robust antiviral effects, and parenteral dosing should be studied."	( Efficacy and tolerability of the oral neuraminidase inhibitor peramivir in experimental human influenza: randomized, controlled trials for prophylaxis and treatment. Barroso, L; Gubareva, L; Hayden, FG; Treanor, J, 2005)	0.33
"19 mg/kg/day in females) corresponding to approximately 72 times above anticipated dosage in human."	( Fertility and early embryonic development toxicity of penequine hydrochloride in mice. Huang, C; Jin, H; Wang, A; Wang, Z; Zhang, Q; Zhang, Z, 2007)	0.34
" However, its duration is not necessarily correlated with drug plasma levels, on which clinical dosing regimens are often based."	( F15063, a potential antipsychotic with dopamine D(2)/D(3) antagonist, 5-HT(1A) agonist and D(4) partial agonist properties: (IV) duration of brain D2-like receptor occupancy and antipsychotic-like activity versus plasma concentration in mice. Assié, MB; Auclair, A; Bardin, L; Consul-Denjean, N; Depoortère, R; Newman-Tancredi, A; Sautel, F, 2007)	0.34
" Specific VIGS of only MPK1 or MPK2 resulted in the same reduction of defense gene expression as cosilencing of MPK1 and MPK2, indicating that gene dosage effects may be important for MPK signaling."	( Tomato MAPKs LeMPK1, LeMPK2, and LeMPK3 function in the systemin-mediated defense response against herbivorous insects. Howe, GA; Jayanty, S; Kandoth, PK; Lincoln, DE; Miller, W; Pancholi, SS; Ranf, S; Stratmann, JW; Walla, MD, 2007)	0.34
" The 120 mg/kg/day dosage also caused reduced mean maternal body weight gains and body weights during the dosage period and reduced absolute and relative maternal feed consumption for the entire dosage period."	( Evaluation of the developmental toxicity of methyl dihydrojasmonate (MDJ) in rats. Api, AM; Christian, MS; Diener, RM; Hoberman, AM; Lewis, EM; Politano, VT, 2008)	0.35
" Unhopped beer was dosed with iso-alpha-acid (Iso), rho-iso-alpha-acid (Rho), tetrahydro-iso-alpha-acid (Tetra), and hexahydro-iso-alpha-acid (Hexa), separately, over a range of concentrations from 2 to 10 ppm."	( Foam-stabilizing effects and cling formation patterns of iso-alpha-acids and reduced iso-alpha-acids in lager beer. Kunimune, T; Shellhammer, TH, 2008)	0.35
" Nasulin has been effective in lowering blood glucose in both normal subjects and diabetes patients, and additional dosing options would allow greater titration flexibility."	( Comparison pharmacokinetics of two concentrations (0.7% and 1.0%) of Nasulin, an ultra-rapid-acting intranasal insulin formulation. Marbury, T; Miller, M; Shi, L; Stote, R; Strange, P, 2010)	0.36
" Clinicians wishing to use peramivir must request authorization from the CDC to confirm patient characteristics warranting its use and to verify the prescriber's understanding of dosing considerations and unapproved status."	( Peramivir: an intravenous neuraminidase inhibitor for the treatment of 2009 H1N1 influenza. Gabay, MP; Mancuso, CE; Steinke, LM; Vanosdol, SJ, )	0.13
" Thus, the dosage of intravenous peramivir was appropriate in these patients."	( Peramivir pharmacokinetics in two critically ill adults with 2009 H1N1 influenza A concurrently receiving continuous renal replacement therapy. Bauer, KA; Bazan, JA; Firstenberg, MS; Goff, DA; Hollister, AS; Mangino, JE; Reed, EE; Shidham, G, 2010)	0.36
" 8a, dosed at 1 and 3 mg/kg po, produced a robust, dose-dependent increase in extracellular serotonin in the frontal cortex of rats, similar to that induced by paroxetine at 5 mg/kg, po."	( Conformationally restricted homotryptamines. Part 7: 3-cis-(3-aminocyclopentyl)indoles as potent selective serotonin reuptake inhibitors. Beno, BR; Deskus, JA; Gao, Q; King, HD; Kozlowski, ES; Lapaglia, MA; Lodge, NJ; Macor, JE; Mattson, GK; Mattson, RJ; Meng, Z; Molski, TF; Sloan, CP; Taber, MT, 2010)	0.36
" Therefore, we performed studies using the in vitro hollow-fiber infection model system to predict optimal dosing regimens for zanamivir against an oseltamivir-sensitive and an oseltamivir-resistant virus."	( Zanamivir, at 600 milligrams twice daily, inhibits oseltamivir-resistant 2009 pandemic H1N1 influenza virus in an in vitro hollow-fiber infection model system. Adams, JR; Brown, AN; Drusano, GL; Kulawy, R; McSharry, JJ; Weng, Q, 2011)	0.37
" Administering PD 0200390 30 min earlier than standard dosing was shown through simulations to reduce latency to persistent sleep by 40%."	( Modeling sleep data for a new drug in development using markov mixed-effects models. Corrigan, B; Karlsson, MO; Kjellsson, MC; Ouellet, D, 2011)	0.37
" dosing to New Zealand white rabbits, the absolute bioavailability for IAA was determined to be 13."	( Bioavailability of hop-derived iso-α-acids and reduced derivatives. Boussery, K; Bracke, M; Cattoor, K; De Keukeleire, D; Deforce, D; Heyerick, A; Remon, JP; Van Bocxlaer, J, 2011)	0.37
"Peramivir, an intravenous investigational neuraminidase inhibitor with activity against influenza viruses, has limited data for dosing in the setting of CVVH."	( Pharmacokinetic assessment of peramivir in a hospitalized adult undergoing continuous venovenous hemofiltration. Ghossein, C; Griffith, MM; Hollister, AS; Ison, MG; Scheetz, MH, 2011)	0.37
" The characteristics of peramivir are not only its capacity for parenteral administration, but also its strong affinity for NA and slow off-rate from the NA-peramivir complex, suggesting that it could lead to a prolonged inhibitory effect and thus allow a lower dosing frequency."	( Efficacy of a single intravenous dose of the neuraminidase inhibitor peramivir in the treatment of equine influenza. Bannai, H; Hobo, S; Kondo, T; Matsumura, T; Minamijima, YH; Muranaka, M; Nemoto, M; Tsujimura, K; Yamada, M; Yamanaka, T, 2012)	0.38
" In addition, fall armyworm larvae show a preference for Tx601 whorl tissue over Mp708 tissue, and the dosage of Tx601 whorl with (E)-beta-caryophyllene repels the fall armyworm."	( A maize line resistant to herbivory constitutively releases (E) -beta-caryophyllene. Brown, AE; Luthe, DS; Sandoya, GV; Shivaji, R; Smith, CL; Smith, WE; Sparks, DL; Williams, WP, 2012)	0.38
" dosing in a mouse."	( A new class of prolylcarboxypeptidase inhibitors, part 2: the aminocyclopentanes. Bhatt, UR; Bleasby, K; Chen, Q; Garcia-Calvo, M; Geissler, WM; Gorski, JN; Graham, TH; Hale, JJ; He, H; Lassman, ME; Li, X; Lisnock, J; Liu, W; Pinto, S; Reibarkh, M; Shen, DM; Shen, Z; Tong, X; Tung, EC; Verras, A; Wiltsie, J; Xiao, J; Xie, D; Xu, S, 2012)	0.62
" • We found that the response of roots was more distinct when the dosage was varied, whereas that of shoots was more distinct when the treatment time was varied."	( Comparative transcriptome analysis of transporters, phytohormone and lipid metabolism pathways in response to arsenic stress in rice (Oryza sativa). Chen, L; Hu, SN; Li, JT; Liao, B; Luo, YF; Shu, WS; Xiao, S; Xie, LJ; Yu, LJ, 2012)	0.38
" To examine the clinical effect of peramivir, the time from dosing to defervescence (body temperature <37."	( [Clinical efficiency in children treated with intravenous drip infusion of peramivir]. Sakata, H, 2011)	0.37
" For example, compound 51 had a good PK profile in both dog and monkey, and exhibited excellent efficacy when dosed orally in an inflammation model in hCCR2 KI mice."	( Novel 2-aminooctahydrocyclopentalene-3a-carboxamides as potent CCR2 antagonists. Cai, C; Hou, C; Johnson, D; Kang, FA; McKenney, S; O'Neill, JC; Opas, E; Sui, Z, 2013)	0.39
" Five-week-old male C57BL/6 mice fed a high fat diet (60% energy from fat) supplemented with lucidone at a dosage of 1250 mg/kg of diet for 12 weeks had reduced body and liver weight, reduced epididymal and perirenal adipose tissue, decreased food efficiency (percentage of weight gain divided by food intake), and lowered plasma cholesterol, triglyceride, glucose, and insulin levels."	( Lucidone from Lindera erythrocarpa Makino fruits suppresses adipogenesis in 3T3-L1 cells and attenuates obesity and consequent metabolic disorders in high-fat diet C57BL/6 mice. Hsieh, YH; Wang, SY, 2013)	0.39
"The effects of methyl jasmonate (MJ) dosage on terpenoid indole alkaloid (TIA) biosynthesis in Catharanthus roseus are correlated with the relative levels of specific MJ-responsive transcription factors."	( Jasmonate-dependent alkaloid biosynthesis in Catharanthus Roseus hairy root cultures is correlated with the relative expression of Orca and Zct transcription factors. Cram, EJ; Goklany, S; Lee-Parsons, CW; Loring, RH; Rizvi, NF, )	0.13
" This open-label, randomized study was initiated during the 2009 H1N1 pandemic to help assess the antiviral activity, safety and tolerability of 5-10 days treatment with two different dosing regimens of the intravenous neuraminidase inhibitor, peramivir, in hospitalized subjects with influenza."	( Intravenous peramivir for treatment of influenza in hospitalized patients. Collis, P; Elder, J; Fraiz, J; Heller, B; Hernandez, JE; Ison, MG; Jauregui, L; Mills, G; O'Neil, B; O'Riordan, W; Playford, EG; Rolf, JD; Sada-Diaz, E; Sheridan, WP, 2014)	0.4
" The production of inflammatory cytokines/chemokines was also significantly suppressed by multiple dosing of peramivir compared with oseltamivir."	( The effect of intravenous peramivir, compared with oral oseltamivir, on the outcome of post-influenza pneumococcal pneumonia in mice. Homma, T; Imamura, Y; Iwanaga, N; Izumikawa, K; Kajihara, T; Kakeya, H; Kitano, M; Kohno, S; Kurihara, S; Miyazaki, T; Nakamura, S; Seki, M; Tanaka, A; Yanagihara, K, 2015)	0.42
" We report on temporal and dosage effects of such crosstalk on host preference and oviposition-site selection behaviour of the herbivorous spider mite Tetranychus urticae towards Lima bean (Phaseolus lunatus) plants, including underlying mechanisms."	( Reciprocal crosstalk between jasmonate and salicylate defence-signalling pathways modulates plant volatile emission and herbivore host-selection behaviour. Dicke, M; Gols, R; Kang, L; Li, N; Menzel, TR; van Loon, JJ; Wei, J, 2014)	0.4
" We evaluated the efficacy of repeated intravenous dosing of the neuraminidase inhibitor peramivir against highly pathogenic avian influenza virus A/Vietnam/UT3040/2004 (H5N1) infection in cynomolgus macaques."	( Efficacy of repeated intravenous administration of peramivir against highly pathogenic avian influenza A (H5N1) virus in cynomolgus macaques. Arikata, M; Ishida, H; Ishigaki, H; Itoh, Y; Kawaoka, Y; Kitagawa, N; Kitano, M; Kobayashi, M; Le, QM; Nakayama, M; Ogasawara, K; Pham, VL; Sato, A; Shichinohe, S; Tsuchiya, H; Yoshida, R, 2014)	0.4
" Peramivir was administrated to mice in three dosing schedules; once, twice and four times after infection of A/WS/33 (H1N1)."	( The relationship between in vivo antiviral activity and pharmacokinetic parameters of peramivir in influenza virus infection model in mice. Baba, K; Hasegawa, T; Homma, T; Izawa, M; Kamimori, H; Kanazu, T; Kida, H; Kitano, M; Kobayashi, M; Kodama, M; Noshi, T; Okazaki, K; Sakoda, Y; Sato, A; Seki, T; Tsuji, M; Yamano, Y; Yoshida, R, 2014)	0.4
" Before the 2009 influenza pandemic, dosing guidelines did not exist for patients receiving continuous renal replacement therapy (CRRT)."	( Peramivir pharmacokinetics in a patient receiving continuous veno-venous hemodiafiltration during the 2009 H1N1 influenza A pandemic. Bentley, ML; Cain, JS; Hansenb, AC; Hollistera, AS; Smith, JA, 2014)	0.4
" These data will be useful in determining appropriate peramivir dosing regimens for severely ill influenza patients with acute renal impairment managed by CVVHDF."	( Peramivir pharmacokinetics in a patient receiving continuous veno-venous hemodiafiltration during the 2009 H1N1 influenza A pandemic. Bentley, ML; Cain, JS; Hansenb, AC; Hollistera, AS; Smith, JA, 2014)	0.4
" Seven of nine other recently reported published studies was a dose-response study."	( Safety and efficacy of peramivir for influenza treatment. Akashi-Ueda, R; Hata, A; Matsumura, T; Takamatsu, K, 2014)	0.4
" There was a 7-day washout period between dosing periods."	( Pharmacokinetic Properties of Peramivir After Single and Multiple Intravenous Infusions in Healthy Chinese Volunteers. Huang, WC; Li, LZ; Lu, HY; Ni, XJ; Peng, H; Shang, DW; Shen, LF; Wang, ZZ; Wen, YG; Xiong, LH; Zhang, M; Zhang, YF, 2016)	0.43
" The results showed that application of pure ( R)-triticonazole, with its high bioactivity and relatively low resistance risk, instead of the racemate in agricultural management would reduce the application dosage required to eliminate carcinogenic mycotoxins and any environmental risks associated with this fungicide, yielding benefits in food safety and environmental protection."	( Mechanistic Insights into Stereospecific Bioactivity and Dissipation of Chiral Fungicide Triticonazole in Agricultural Management. Gao, B; Sanganyado, E; Shi, H; Tang, B; Tian, M; Wang, M; Zhang, Q; Zhang, Z, 2018)	0.48
" Diet-induced obese mice (DIO) were dosed orally with KDT501 and acute effects on glucose homeostasis determined."	( Intestinal bitter taste receptor activation alters hormone secretion and imparts metabolic benefits. Albert, V; Behrens, M; Bland, JS; Fang, M; Galmozzi, A; Godio, C; Grayson, N; Kim, SM; Kim, W; Kok, BP; Littlejohn, NK; Meyerhof, W; Saez, E; Siuzdak, G; Srinivasan, S, 2018)	0.48
" The validated methods were applied to the analysis of PEN-citrate in the dosage form and human serum samples where the drug was successfully resolved from the pharmaceutical additives and serum components with recoveries ≥98."	( Extraction-free spectrophotometric assay of the antitussive drug pentoxyverine citrate using sulfonephthalein dyes. Elfeky, SA; Issa, YM; Mohamed, SH, 2019)	0.51
" All patients had adjustments made to their dosing interval to a more frequent interval."	( Peramivir for Influenza A and B Viral Infections: A Pharmacokinetic Case Series. Chopra, A; Cies, JJ; Enache, A; Moore, WS, 2019)	0.51
"The pharmacokinetics of PRV demonstrated in this PICU cohort differs in comparison to healthy pediatric and adult patients, and alterations to dosing regimens may be needed in PICU patients to achieve pharmacodynamic exposures."	( Peramivir for Influenza A and B Viral Infections: A Pharmacokinetic Case Series. Chopra, A; Cies, JJ; Enache, A; Moore, WS, 2019)	0.51
" Our electrophysiological results show a dose-response relationship between the EAG amplitudes and the increasing concentrations of the olfactory compound."	( Association between olfactory sensitivity and behavioral responses of Drosophila suzukii to naturally occurring volatile compounds. Corda, G; Crnjar, R; Delogu, G; Dettori, MA; Fabbri, D; Solari, P; Sollai, G, 2020)	0.56
"Findings will provide timely information on the safety, efficacy, and optimal dosing of t-PA to treat moderate/severe COVID-19-induced ARDS, which can be rapidly adapted to a phase III trial (NCT04357730; FDA IND 149634)."	( Abbasi, S; Abd El-Wahab, A; Abdallah, M; Abebe, G; Aca-Aca, G; Adama, S; Adefegha, SA; Adidigue-Ndiome, R; Adiseshaiah, P; Adrario, E; Aghajanian, C; Agnese, W; Ahmad, A; Ahmad, I; Ahmed, MFE; Akcay, OF; Akinmoladun, AC; Akutagawa, T; Alakavuklar, MA; Álava-Rabasa, S; Albaladejo-Florín, MJ; Alexandra, AJE; Alfawares, R; Alferiev, IS; Alghamdi, HS; Ali, I; Allard, B; Allen, JD; Almada, E; Alobaid, A; Alonso, GL; Alqahtani, YS; Alqarawi, W; Alsaleh, H; Alyami, BA; Amaral, BPD; Amaro, JT; Amin, SAW; Amodio, E; Amoo, ZA; Andia Biraro, I; Angiolella, L; Anheyer, D; Anlay, DZ; Annex, BH; Antonio-Aguirre, B; Apple, S; Arbuznikov, AV; Arinsoy, T; Armstrong, DK; Ash, S; Aslam, M; Asrie, F; Astur, DC; Atzrodt, J; Au, DW; Aucoin, M; Auerbach, EJ; Azarian, S; Ba, D; Bai, Z; Baisch, PRM; Balkissou, AD; Baltzopoulos, V; Banaszewski, M; Banerjee, S; Bao, Y; Baradwan, A; Barandika, JF; Barger, PM; Barion, MRL; Barrett, CD; Basudan, AM; Baur, LE; Baz-Rodríguez, SA; Beamer, P; Beaulant, A; Becker, DF; Beckers, C; Bedel, J; Bedlack, R; Bermúdez de Castro, JM; Berry, JD; Berthier, C; Bhattacharya, D; Biadgo, B; Bianco, G; Bianco, M; Bibi, S; Bigliardi, AP; Billheimer, D; Birnie, DH; Biswas, K; Blair, HC; Bognetti, P; Bolan, PJ; Bolla, JR; Bolze, A; Bonnaillie, P; Borlimi, R; Bórquez, J; Bottari, NB; Boulleys-Nana, JR; Brighetti, G; Brodeur, GM; Budnyak, T; Budnyk, S; Bukirwa, VD; Bulman, DM; Burm, R; Busman-Sahay, K; Butcher, TW; Cai, C; Cai, H; Cai, L; Cairati, M; Calvano, CD; Camacho-Ordóñez, A; Camela, E; Cameron, T; Campbell, BS; Cansian, RL; Cao, Y; Caporale, AS; Carciofi, AC; Cardozo, V; Carè, J; Carlos, AF; Carozza, R; Carroll, CJW; Carsetti, A; Carubelli, V; Casarotta, E; Casas, M; Caselli, G; Castillo-Lora, J; Cataldi, TRI; Cavalcante, ELB; Cavaleiro, A; Cayci, Z; Cebrián-Tarancón, C; Cedrone, E; Cella, D; Cereda, C; Ceretti, A; Ceroni, M; Cha, YH; Chai, X; Chang, EF; Chang, TS; Chanteux, H; Chao, M; Chaplin, BP; Chaturvedi, S; Chaturvedi, V; Chaudhary, DK; Chen, A; Chen, C; Chen, HY; Chen, J; Chen, JJ; Chen, K; Chen, L; Chen, Q; Chen, R; Chen, SY; Chen, TY; Chen, WM; Chen, X; Chen, Y; Cheng, G; Cheng, GJ; Cheng, J; Cheng, YH; Cheon, HG; Chew, KW; Chhoker, S; Chiu, WN; Choi, ES; Choi, MJ; Choi, SD; Chokshi, S; Chorny, M; Chu, KI; Chu, WJ; Church, AL; Cirrincione, A; Clamp, AR; Cleff, MB; Cohen, M; Coleman, RL; Collins, SL; Colombo, N; Conduit, N; Cong, WL; Connelly, MA; Connor, J; Cooley, K; Correa Ramos Leal, I; Cose, S; Costantino, C; Cottrell, M; Cui, L; Cundall, J; Cutaia, C; Cutler, CW; Cuypers, ML; da Silva Júnior, FMR; Dahal, RH; Damiani, E; Damtie, D; Dan-Li, W; Dang, Z; Dasa, SSK; Davin, A; Davis, DR; de Andrade, CM; de Jong, PL; de Oliveira, D; de Paula Dorigam, JC; Dean, A; Deepa, M; Delatour, C; Dell'Aiera, S; Delley, MF; den Boer, RB; Deng, L; Deng, Q; Depner, RM; Derdau, V; Derici, U; DeSantis, AJ; Desmarini, D; Diffo-Sonkoue, L; Divizia, M; Djenabou, A; Djordjevic, JT; Dobrovolskaia, MA; Domizi, R; Donati, A; Dong, Y; Dos Santos, M; Dos Santos, MP; Douglas, RG; Duarte, PF; Dullaart, RPF; Duscha, BD; Edwards, LA; Edwards, TE; Eichenwald, EC; El-Baba, TJ; Elashiry, M; Elashiry, MM; Elashry, SH; Elliott, A; Elsayed, R; Emerson, MS; Emmanuel, YO; Emory, TH; Endale-Mangamba, LM; Enten, GA; Estefanía-Fernández, K; Estes, JD; Estrada-Mena, FJ; Evans, S; Ezra, L; Faria de, RO; Farraj, AK; Favre, C; Feng, B; Feng, J; Feng, L; Feng, W; Feng, X; Feng, Z; Fernandes, CLF; Fernández-Cuadros, ME; Fernie, AR; Ferrari, D; Florindo, PR; Fong, PC; Fontes, EPB; Fontinha, D; Fornari, VJ; Fox, NP; Fu, Q; Fujitaka, Y; Fukuhara, K; Fumeaux, T; Fuqua, C; Fustinoni, S; Gabbanelli, V; Gaikwad, S; Gall, ET; Galli, A; Gancedo, MA; Gandhi, MM; Gao, D; Gao, K; Gao, M; Gao, Q; Gao, X; Gao, Y; Gaponenko, V; Garber, A; Garcia, EM; García-Campos, C; García-Donas, J; García-Pérez, AL; Gasparri, F; Ge, C; Ge, D; Ge, JB; Ge, X; George, I; George, LA; Germani, G; Ghassemi Tabrizi, S; Gibon, Y; Gillent, E; Gillies, RS; Gilmour, MI; Goble, S; Goh, JC; Goiri, F; Goldfinger, LE; Golian, M; Gómez, MA; Gonçalves, J; Góngora-García, OR; Gonul, I; González, MA; Govers, TM; Grant, PC; Gray, EH; Gray, JE; Green, MS; Greenwald, I; Gregory, MJ; Gretzke, D; Griffin-Nolan, RJ; Griffith, DC; Gruppen, EG; Guaita, A; Guan, P; Guan, X; Guerci, P; Guerrero, DT; Guo, M; Guo, P; Guo, R; Guo, X; Gupta, J; Guz, G; Hajizadeh, N; Hamada, H; Haman-Wabi, AB; Han, TT; Hannan, N; Hao, S; Harjola, VP; Harmon, M; Hartmann, MSM; Hartwig, JF; Hasani, M; Hawthorne, WJ; Haykal-Coates, N; Hazari, MS; He, DL; He, P; He, SG; Héau, C; Hebbar Kannur, K; Helvaci, O; Heuberger, DM; Hidalgo, F; Hilty, MP; Hirata, K; Hirsch, A; Hoffman, AM; Hoffmann, JF; Holloway, RW; Holmes, RK; Hong, S; Hongisto, M; Hopf, NB; Hörlein, R; Hoshino, N; Hou, Y; Hoven, NF; Hsieh, YY; Hsu, CT; Hu, CW; Hu, JH; Hu, MY; Hu, Y; Hu, Z; Huang, C; Huang, D; Huang, DQ; Huang, L; Huang, Q; Huang, R; Huang, S; Huang, SC; Huang, W; Huang, Y; Huffman, KM; Hung, CH; Hung, CT; Huurman, R; Hwang, SM; Hyun, S; Ibrahim, AM; Iddi-Faical, A; Immordino, P; Isla, MI; Jacquemond, V; Jacques, T; Jankowska, E; Jansen, JA; Jäntti, T; Jaque-Fernandez, F; Jarvis, GA; Jatt, LP; Jeon, JW; Jeong, SH; Jhunjhunwala, R; Ji, F; Jia, X; Jia, Y; Jian-Bo, Z; Jiang, GD; Jiang, L; Jiang, W; Jiang, WD; Jiang, Z; Jiménez-Hoyos, CA; Jin, S; Jobling, MG; John, CM; John, T; Johnson, CB; Jones, KI; Jones, WS; Joseph, OO; Ju, C; Judeinstein, P; Junges, A; Junnarkar, M; Jurkko, R; Kaleka, CC; Kamath, AV; Kang, X; Kantsadi, AL; Kapoor, M; Karim, Z; Kashuba, ADM; Kassa, E; Kasztura, M; Kataja, A; Katoh, T; Kaufman, JS; Kaupp, M; Kehinde, O; Kehrenberg, C; Kemper, N; Kerr, CW; Khan, AU; Khan, MF; Khan, ZUH; Khojasteh, SC; Kilburn, S; Kim, CG; Kim, DU; Kim, DY; Kim, HJ; Kim, J; Kim, OH; Kim, YH; King, C; Klein, A; Klingler, L; Knapp, AK; Ko, TK; Kodavanti, UP; Kolla, V; Kong, L; Kong, RY; Kong, X; Kore, S; Kortz, U; Korucu, B; Kovacs, A; Krahnert, I; Kraus, WE; Kuang, SY; Kuehn-Hajder, JE; Kurz, M; Kuśtrowski, P; Kwak, YD; Kyttaris, VC; Laga, SM; Laguerre, A; Laloo, A; Langaro, MC; Langham, MC; Lao, X; Larocca, MC; Lassus, J; Lattimer, TA; Lazar, S; Le, MH; Leal, DB; Leal, M; Leary, A; Ledermann, JA; Lee, JF; Lee, MV; Lee, NH; Leeds, CM; Leeds, JS; Lefrandt, JD; Leicht, AS; Leonard, M; Lev, S; Levy, K; Li, B; Li, C; Li, CM; Li, DH; Li, H; Li, J; Li, L; Li, LJ; Li, N; Li, P; Li, T; Li, X; Li, XH; Li, XQ; Li, XX; Li, Y; Li, Z; Li, ZY; Liao, YF; Lin, CC; Lin, MH; Lin, Y; Ling, Y; Links, TP; Lira-Romero, E; Liu, C; Liu, D; Liu, H; Liu, J; Liu, L; Liu, LP; Liu, M; Liu, T; Liu, W; Liu, X; Liu, XH; Liu, Y; Liuwantara, D; Ljumanovic, N; Lobo, L; Lokhande, K; Lopes, A; Lopes, RMRM; López-Gutiérrez, JC; López-Muñoz, MJ; López-Santamaría, M; Lorenzo, C; Lorusso, D; Losito, I; Lu, C; Lu, H; Lu, HZ; Lu, SH; Lu, SN; Lu, Y; Lu, ZY; Luboga, F; Luo, JJ; Luo, KL; Luo, Y; Lutomski, CA; Lv, W; M Piedade, MF; Ma, J; Ma, JQ; Ma, JX; Ma, N; Ma, P; Ma, S; Maciel, M; Madureira, M; Maganaris, C; Maginn, EJ; Mahnashi, MH; Maierhofer, M; Majetschak, M; Malla, TR; Maloney, L; Mann, DL; Mansuri, A; Marelli, E; Margulis, CJ; Marrella, A; Martin, BL; Martín-Francés, L; Martínez de Pinillos, M; Martínez-Navarro, EM; Martinez-Quintanilla Jimenez, D; Martínez-Velasco, A; Martínez-Villaseñor, L; Martinón-Torres, M; Martins, BA; Massongo, M; Mathew, AP; Mathews, D; Matsui, J; Matsumoto, KI; Mau, T; Maves, RC; Mayclin, SJ; Mayer, JM; Maynard, ND; Mayr, T; Mboowa, MG; McEvoy, MP; McIntyre, RC; McKay, JA; McPhail, MJW; McVeigh, AL; Mebazaa, A; Medici, V; Medina, DN; Mehmood, T; Mei-Li, C; Melku, M; Meloncelli, S; Mendes, GC; Mendoza-Velásquez, C; Mercadante, R; Mercado, MI; Merenda, MEZ; Meunier, J; Mi, SL; Michels, M; Mijatovic, V; Mikhailov, V; Milheiro, SA; Miller, DC; Ming, F; Mitsuishi, M; Miyashita, T; Mo, J; Mo, S; Modesto-Mata, M; Moeller, S; Monte, A; Monteiro, L; Montomoli, J; Moore, EE; Moore, HB; Moore, PK; Mor, MK; Moratalla-López, N; Moratilla Lapeña, L; Moreira, R; Moreno, MA; Mörk, AC; Morton, M; Mosier, JM; Mou, LH; Mougharbel, AS; Muccillo-Baisch, AL; Muñoz-Serrano, AJ; Mustafa, B; Nair, GM; Nakanishi, I; Nakanjako, D; Naraparaju, K; Nawani, N; Neffati, R; Neil, EC; Neilipovitz, D; Neira-Borrajo, I; Nelson, MT; Nery, PB; Nese, M; Nguyen, F; Nguyen, MH; Niazy, AA; Nicolaï, J; Nogueira, F; Norbäck, D; Novaretti, JV; O'Donnell, T; O'Dowd, A; O'Malley, DM; Oaknin, A; Ogata, K; Ohkubo, K; Ojha, M; Olaleye, MT; Olawande, B; Olomo, EJ; Ong, EWY; Ono, A; Onwumere, J; Ortiz Bibriesca, DM; Ou, X; Oza, AM; Ozturk, K; Özütemiz, C; Palacio-Pastrana, C; Palaparthi, A; Palevsky, PM; Pan, K; Pantanetti, S; Papachristou, DJ; Pariani, A; Parikh, CR; Parissis, J; Paroul, N; Parry, S; Patel, N; Patel, SM; Patel, VC; Pawar, S; Pefura-Yone, EW; Peixoto Andrade, BCO; Pelepenko, LE; Peña-Lora, D; Peng, S; Pérez-Moro, OS; Perez-Ortiz, AC; Perry, LM; Peter, CM; Phillips, NJ; Phillips, P; Pia Tek, J; Piner, LW; Pinto, EA; Pinto, SN; Piyachaturawat, P; Poka-Mayap, V; Polledri, E; Poloni, TE; Ponessa, G; Poole, ST; Post, AK; Potter, TM; Pressly, BB; Prouty, MG; Prudêncio, M; Pulkki, K; Pupier, C; Qian, H; Qian, ZP; Qiu, Y; Qu, G; Rahimi, S; Rahman, AU; Ramadan, H; Ramanna, S; Ramirez, I; Randolph, GJ; Rasheed, A; Rault, J; Raviprakash, V; Reale, E; Redpath, C; Rema, V; Remucal, CK; Remy, D; Ren, T; Ribeiro, LB; Riboli, G; Richards, J; Rieger, V; Rieusset, J; Riva, A; Rivabella Maknis, T; Robbins, JL; Robinson, CV; Roche-Campo, F; Rodriguez, R; Rodríguez-de-Cía, J; Rollenhagen, JE; Rosen, EP; Rub, D; Rubin, N; Rubin, NT; Ruurda, JP; Saad, O; Sabell, T; Saber, SE; Sabet, M; Sadek, MM; Saejio, A; Salinas, RM; Saliu, IO; Sande, D; Sang, D; Sangenito, LS; Santos, ALSD; Sarmiento Caldas, MC; Sassaroli, S; Sassi, V; Sato, J; Sauaia, A; Saunders, K; Saunders, PR; Savarino, SJ; Scambia, G; Scanlon, N; Schetinger, MR; Schinkel, AFL; Schladweiler, MC; Schofield, CJ; Schuepbach, RA; Schulz, J; Schwartz, N; Scorcella, C; Seeley, J; Seemann, F; Seinige, D; Sengoku, T; Seravalli, J; Sgromo, B; Shaheen, MY; Shan, L; Shanmugam, S; Shao, H; Sharma, S; Shaw, KJ; Shen, BQ; Shen, CH; Shen, P; Shen, S; Shen, Y; Shen, Z; Shi, J; Shi-Li, L; Shimoda, K; Shoji, Y; Shun, C; Silva, MA; Silva-Cardoso, J; Simas, NK; Simirgiotis, MJ; Sincock, SA; Singh, MP; Sionis, A; Siu, J; Sivieri, EM; Sjerps, MJ; Skoczen, SL; Slabon, A; Slette, IJ; Smith, MD; Smith, S; Smith, TG; Snapp, KS; Snow, SJ; Soares, MCF; Soberman, D; Solares, MD; Soliman, I; Song, J; Sorooshian, A; Sorrell, TC; Spinar, J; Staudt, A; Steinhart, C; Stern, ST; Stevens, DM; Stiers, KM; Stimming, U; Su, YG; Subbian, V; Suga, H; Sukhija-Cohen, A; Suksamrarn, A; Suksen, K; Sun, J; Sun, M; Sun, P; Sun, W; Sun, XF; Sun, Y; Sundell, J; Susan, LF; Sutjarit, N; Swamy, KV; Swisher, EM; Sykes, C; Takahashi, JA; Talmor, DS; Tan, B; Tan, ZK; Tang, L; Tang, S; Tanner, JJ; Tanwar, M; Tarazi, Z; Tarvasmäki, T; Tay, FR; Teketel, A; Temitayo, GI; Thersleff, T; Thiessen Philbrook, H; Thompson, LC; Thongon, N; Tian, B; Tian, F; Tian, Q; Timothy, AT; Tingle, MD; Titze, IR; Tolppanen, H; Tong, W; Toyoda, H; Tronconi, L; Tseng, CH; Tu, H; Tu, YJ; Tung, SY; Turpault, S; Tuynman, JB; Uemoto, AT; Ugurlu, M; Ullah, S; Underwood, RS; Ungell, AL; Usandizaga-Elio, I; Vakonakis, I; van Boxel, GI; van den Beucken, JJJP; van der Boom, T; van Slegtenhorst, MA; Vanni, JR; Vaquera, A; Vasconcellos, RS; Velayos, M; Vena, R; Ventura, G; Verso, MG; Vincent, RP; Vitale, F; Vitali, S; Vlek, SL; Vleugels, MPH; Volkmann, N; Vukelic, M; Wagner Mackenzie, B; Wairagala, P; Waller, SB; Wan, J; Wan, MT; Wan, Y; Wang, CC; Wang, H; Wang, J; Wang, JF; Wang, K; Wang, L; Wang, M; Wang, S; Wang, WM; Wang, X; Wang, Y; Wang, YD; Wang, YF; Wang, Z; Wang, ZG; Warriner, K; Weberpals, JI; Weerachayaphorn, J; Wehrli, FW; Wei, J; Wei, KL; Weinheimer, CJ; Weisbord, SD; Wen, S; Wendel Garcia, PD; Williams, JW; Williams, R; Winkler, C; Wirman, AP; Wong, S; Woods, CM; Wu, B; Wu, C; Wu, F; Wu, P; Wu, S; Wu, Y; Wu, YN; Wu, ZH; Wurtzel, JGT; Xia, L; Xia, Z; Xia, ZZ; Xiao, H; Xie, C; Xin, ZM; Xing, Y; Xing, Z; Xu, S; Xu, SB; Xu, T; Xu, X; Xu, Y; Xue, L; Xun, J; Yaffe, MB; Yalew, A; Yamamoto, S; Yan, D; Yan, H; Yan, S; Yan, X; Yang, AD; Yang, E; Yang, H; Yang, J; Yang, JL; Yang, K; Yang, M; Yang, P; Yang, Q; Yang, S; Yang, W; Yang, X; Yang, Y; Yao, JC; Yao, WL; Yao, Y; Yaqub, TB; Ye, J; Ye, W; Yen, CW; Yeter, HH; Yin, C; Yip, V; Yong-Yi, J; Yu, HJ; Yu, MF; Yu, S; Yu, W; Yu, WW; Yu, X; Yuan, P; Yuan, Q; Yue, XY; Zaia, AA; Zakhary, SY; Zalwango, F; Zamalloa, A; Zamparo, P; Zampini, IC; Zani, JL; Zeitoun, R; Zeng, N; Zenteno, JC; Zepeda-Palacio, C; Zhai, C; Zhang, B; Zhang, G; Zhang, J; Zhang, K; Zhang, Q; Zhang, R; Zhang, T; Zhang, X; Zhang, Y; Zhang, YY; Zhao, B; Zhao, D; Zhao, G; Zhao, H; Zhao, Q; Zhao, R; Zhao, S; Zhao, T; Zhao, X; Zhao, XA; Zhao, Y; Zhao, Z; Zheng, Z; Zhi-Min, G; Zhou, CL; Zhou, HD; Zhou, J; Zhou, W; Zhou, XQ; Zhou, Z; Zhu, C; Zhu, H; Zhu, L; Zhu, Y; Zitzmann, N; Zou, L; Zou, Y, 2022)	0.72
"Peramivir offers a single-dose intravenous (IV) treatment option for influenza (vs 5-day oral dosing for oseltamivir)."	( Intravenous peramivir vs oral oseltamivir in high-risk emergency department patients with influenza: Results from a pilot randomized controlled study. Dugas, AF; Hsieh, YH; LoVecchio, F; McBryde, B; Ricketts, EP; Rothman, RE; Saliba-Shaw, K, 2021)	0.62
" Therefore, the use of nanotechnology could be a good option for improving the quality of wines from an aromatic point of view, while reducing the necessary dosage of agrochemicals, in line with more sustainable agricultural practices."	( Effects of Methyl Jasmonate and Nano-Methyl Jasmonate Treatments on Monastrell Wine Volatile Composition. Bleda-Sánchez, JA; Delgado-López, JM; Fernández-Fernández, JI; Gil-Muñoz, R; Giménez-Bañón, MJ; Moreno-Olivares, JD; Paladines-Quezada, DF; Parra-Torrejón, B, 2022)	0.72
" We report here that dosage differences in a cluster of monocot-specific 12-OXOPHYTODIENOATE REDUCTASE genes from subfamily III (OPRIII) modulate key differences in wheat root architecture, which are associated with grain yield under water-limited conditions."	( Dosage differences in 12-OXOPHYTODIENOATE REDUCTASE genes modulate wheat root growth. Burguener, GF; Cho, MJ; Dehesh, K; Dubcovsky, J; Fahima, T; Gabay, G; Gou, JY; Gualano, LD; Hamberg, M; Howell, T; Ke, H; Lukaszewski, A; Moriconi, JI; Santa-María, GE; Staskawicz, B; Tanaka, J; Wang, H; Zhang, GL; Zhang, J, 2023)	0.91

Role	Description
non-polar solvent	null
[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
cyclopentanes	Cyclopentane and its derivatives formed by substitution.
cycloalkane	Saturated monocyclic hydrocarbons (with or without side chains).
volatile organic compound	Any organic compound having an initial boiling point less than or equal to 250 degreeC (482 degreeF) measured at a standard atmospheric pressure of 101.3 kPa.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
RAR-related orphan receptor gamma	Mus musculus (house mouse)	Potency	0.0119	0.0060	38.0041	19,952.5996	AID1159521
AR protein	Homo sapiens (human)	Potency	17.3210	0.0002	21.2231	8,912.5098	AID743036; AID743040; AID743042
glucocorticoid receptor [Homo sapiens]	Homo sapiens (human)	Potency	30.2428	0.0002	14.3764	60.0339	AID720691
cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_a	Homo sapiens (human)	Potency	29.9847	0.0017	23.8393	78.1014	AID743083
lethal factor (plasmid)	Bacillus anthracis str. A2012	Potency	25.1189	0.0200	10.7869	31.6228	AID912
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Assay ID	Title	Year	Journal	Article
AID603957	Octanol-water partition coefficient, log P of the compound	2008	European journal of medicinal chemistry, Apr, Volume: 43, Issue:4	QSPR modeling of octanol/water partition coefficient for vitamins by optimal descriptors calculated with SMILES.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	908 (8.83)	18.7374
1990's	1212 (11.78)	18.2507
2000's	2543 (24.72)	29.6817
2010's	4453 (43.28)	24.3611
2020's	1172 (11.39)	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	86 (0.82%)	5.53%
Reviews	550 (5.24%)	6.00%
Case Studies	37 (0.35%)	4.05%
Observational	5 (0.05%)	0.25%
Other	9,820 (93.54%)	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
ethylene dichloride ethylene dichloride: RN given refers to 1,2-isomer; structure given in first source. 1,2-dichloroethane : A member of the class of chloroethanes substituted by two chloro groups at positions 1 and 2.	2.04	1	0	chloroethanes	hepatotoxic agent; mutagen; non-polar solvent
1,2,4-trichlorobenzene 1,2,4-trichlorobenzene : A trichlorobenzene with chloro substituents at positions 1, 2 and 4.	2.04	1	0	trichlorobenzene
alpha-ketobutyric acid alpha-ketobutyric acid: RN given refers to parent cpd; structure. 2-oxobutanoic acid : A 2-oxo monocarboxylic acid that is the 2-oxo derivative of butanoic acid.	2.03	1	0	2-oxo monocarboxylic acid; short-chain fatty acid
2-methyl-butan-1,2,3,4-tetraol-2,4-cyclopyrophosphate 2-methyl-butan-1,2,3,4-tetraol-2,4-cyclopyrophosphate: structure given in first source	2.57	2	0
5-enolpyruvoylshikimate-3-phosphate 5-enolpyruvoylshikimate-3-phosphate: structure given in first source	2.02	1	0
acetoacetic acid acetoacetic acid : A 3-oxo monocarboxylic acid that is butyric acid bearing a 3-oxo substituent.	2.04	1	0	3-oxo fatty acid; ketone body	metabolite
phosphoserine Phosphoserine: The phosphoric acid ester of serine.	2	1	0	non-proteinogenic alpha-amino acid; O-phosphoamino acid; serine derivative	human 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.	6.09	38	0	amino acid zwitterion; gamma-amino acid; monocarboxylic acid	human metabolite; neurotransmitter; Saccharomyces cerevisiae metabolite; signalling molecule
4-hydroxybenzoic acid 4-hydroxybenzoic acid : A monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring.	2.48	2	0	monohydroxybenzoic acid	algal metabolite; plant metabolite
aminolevulinic acid Aminolevulinic Acid: A compound produced from succinyl-CoA and GLYCINE as an intermediate in heme synthesis. It is used as a PHOTOCHEMOTHERAPY for actinic KERATOSIS.. 5-aminolevulinic acid : The simplest delta-amino acid in which the hydrogens at the gamma position are replaced by an oxo group. It is metabolised to protoporphyrin IX, a photoactive compound which accumulates in the skin. Used (in the form of the hydrochloride salt)in combination with blue light illumination for the treatment of minimally to moderately thick actinic keratosis of the face or scalp.	1.95	1	0	4-oxo monocarboxylic acid; amino acid zwitterion; delta-amino acid	antineoplastic agent; dermatologic drug; Escherichia coli metabolite; human metabolite; mouse metabolite; photosensitizing agent; plant metabolite; prodrug; Saccharomyces cerevisiae metabolite
5-hydroxytryptophan 5-Hydroxytryptophan: The immediate precursor in the biosynthesis of SEROTONIN from tryptophan. It is used as an antiepileptic and antidepressant.. 5-hydroxytryptophan : A tryptophan derivative that is tryptophan substituted by a hydroxy group at position 5.	1.95	1	0	hydroxytryptophan	human metabolite; neurotransmitter
phosphoribosyl-n-formylglycineamide [no description available]	1.97	1	0
ethylene glycol Ethylene Glycol: A colorless, odorless, viscous dihydroxy alcohol. It has a sweet taste, but is poisonous if ingested. Ethylene glycol is the most important glycol commercially available and is manufactured on a large scale in the United States. It is used as an antifreeze and coolant, in hydraulic fluids, and in the manufacture of low-freezing dynamites and resins.. ethanediol : Any diol that is ethane or substituted ethane carrying two hydroxy groups.. ethylene glycol : A 1,2-glycol compound produced via reaction of ethylene oxide with water.	2.43	2	0	ethanediol; glycol	metabolite; mouse metabolite; solvent; toxin
acetic acid Acetic Acid: Product of the oxidation of ethanol and of the destructive distillation of wood. It is used locally, occasionally internally, as a counterirritant and also as a reagent. (Stedman, 26th ed). acetic acid : A simple monocarboxylic acid containing two carbons.	3.52	7	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.	2.54	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).	8.81	11	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]	4.67	28	0	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
agmatine Agmatine: Decarboxylated arginine, isolated from several plant and animal sources, e.g., pollen, ergot, herring sperm, octopus muscle.	2.81	3	0	guanidines; primary amino compound	Escherichia coli metabolite; mouse metabolite
allantoin [no description available]	2.9	3	0	imidazolidine-2,4-dione; ureas	Escherichia coli metabolite; human metabolite; Saccharomyces cerevisiae metabolite; vulnerary
ammonium hydroxide azane : Saturated acyclic nitrogen hydrides having the general formula NnHn+2.	3.11	5	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
anthranilic acid anthranilic acid: RN given refers to parent cpd; structure in Negwer, 5th ed, #565. anthranilic acid : An aminobenzoic acid that is benzoic acid having a single amino substituent located at position 2. It is a metabolite produced in L-tryptophan-kynurenine pathway in the central nervous system.	2.46	2	0	aminobenzoic acid	human metabolite; mouse metabolite
quinacrine Quinacrine: An acridine derivative formerly widely used as an antimalarial but superseded by chloroquine in recent years. It has also been used as an anthelmintic and in the treatment of giardiasis and malignant effusions. It is used in cell biological experiments as an inhibitor of phospholipase A2.. quinacrine : A member of the class of acridines that is acridine substituted by a chloro group at position 6, a methoxy group at position 2 and a [5-(diethylamino)pentan-2-yl]nitrilo group at position 9.	1.99	1	0	acridines; aromatic ether; organochlorine compound; tertiary amino compound	antimalarial; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor
beta-alanine [no description available]	2.1	1	0	amino acid zwitterion; beta-amino acid	agonist; fundamental metabolite; human metabolite; inhibitor; neurotransmitter
benzaldehyde [no description available]	2.25	1	0	benzaldehydes	EC 3.1.1.3 (triacylglycerol lipase) inhibitor; EC 3.5.5.1 (nitrilase) inhibitor; flavouring agent; fragrance; odorant receptor agonist; plant metabolite
benzene [no description available]	5.35	18	0	aromatic annulene; benzenes; volatile organic compound	carcinogenic agent; environmental contaminant; non-polar solvent
benzoic acid Benzoic Acid: A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid.. benzoic acid : A compound comprising a benzene ring core carrying a carboxylic acid substituent.. aromatic carboxylic acid : Any carboxylic acid in which the carboxy group is directly bonded to an aromatic ring.	4.54	7	0	benzoic acids	algal metabolite; antimicrobial food preservative; drug allergen; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 3.1.1.3 (triacylglycerol lipase) inhibitor; human xenobiotic metabolite; plant metabolite
benzyl alcohol Benzyl Alcohol: A colorless liquid with a sharp burning taste and slight odor. It is used as a local anesthetic and to reduce pain associated with LIDOCAINE injection. Also, it is used in the manufacture of other benzyl compounds, as a pharmaceutic aid, and in perfumery and flavoring.. hydroxytoluene : Any member of the class of toluenes carrying one or more hydroxy substituents.. benzyl alcohol : An aromatic alcohol that consists of benzene bearing a single hydroxymethyl substituent.. aromatic alcohol : Any alcohol in which the alcoholic hydroxy group is attached to a carbon which is itself bonded to an aromatic ring.. aromatic primary alcohol : Any primary alcohol in which the alcoholic hydroxy group is attached to a carbon which is itself bonded to an aromatic ring.	2.36	2	0	benzyl alcohols	antioxidant; fragrance; metabolite; solvent
betaine glycine betaine : The amino acid betaine derived from glycine.	5.49	3	1	amino-acid betaine; glycine derivative	fundamental metabolite
bromide Bromides: Salts of hydrobromic acid, HBr, with the bromine atom in the 1- oxidation state. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	3.1	5	0	halide anion; monoatomic bromine
butyraldehyde [no description available]	3.35	1	0	butanals	biomarker; Escherichia coli metabolite; mouse metabolite
2,3-butylene glycol 2,3-butylene glycol: RN given refers to cpd without isomeric designation. butane-2,3-diol : A butanediol in which hydroxylation is at C-2 and C-3.	2.04	1	0	butanediol; glycol; secondary alcohol
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.	5.05	5	2	alkyl alcohol; primary alcohol; short-chain primary fatty alcohol	human metabolite; mouse metabolite; protic solvent
butyric acid Butyric Acid: A four carbon acid, CH3CH2CH2COOH, with an unpleasant odor that occurs in butter and animal fat as the glycerol ester.. butyrate : A short-chain fatty acid anion that is the conjugate base of butyric acid, obtained by deprotonation of the carboxy group.. butyric acid : A straight-chain saturated fatty acid that is butane in which one of the terminal methyl groups has been oxidised to a carboxy group.	2.49	2	0	fatty acid 4:0; straight-chain saturated fatty acid	human urinary metabolite; Mycoplasma genitalium metabolite
cadaverine [no description available]	1.98	1	0	alkane-alpha,omega-diamine	Daphnia magna metabolite; Escherichia coli metabolite; mouse metabolite; plant metabolite
carbamates [no description available]	3.78	11	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.	3.75	10	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
formic acid formic acid: RN given refers to parent cpd. formic acid : The simplest carboxylic acid, containing a single carbon. Occurs naturally in various sources including the venom of bee and ant stings, and is a useful organic synthetic reagent. Principally used as a preservative and antibacterial agent in livestock feed. Induces severe metabolic acidosis and ocular injury in human subjects.	3.74	3	0	monocarboxylic acid	antibacterial agent; astringent; metabolite; protic solvent; solvent
carnitine [no description available]	2.35	2	0	amino-acid betaine	human metabolite; mouse metabolite
catechol [no description available]	1.99	1	0	catechols	allelochemical; genotoxin; plant metabolite
methane Methane: The simplest saturated hydrocarbon. It is a colorless, flammable gas, slightly soluble in water. It is one of the chief constituents of natural gas and is formed in the decomposition of organic matter. (Grant & Hackh's Chemical Dictionary, 5th ed). methane : A one-carbon compound in which the carbon is attached by single bonds to four hydrogen atoms. It is a colourless, odourless, non-toxic but flammable gas (b.p. -161degreeC).	5.16	44	0	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
chlordecone [no description available]	1.95	1	0	cyclic ketone; organochlorine compound	insecticide; persistent organic pollutant
choline [no description available]	7.13	16	1	cholines	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter; nutrient; plant metabolite; Saccharomyces cerevisiae metabolite
citric acid, anhydrous Citric Acid: A key intermediate in metabolism. It is an acid compound found in citrus fruits. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability.. citric acid : A tricarboxylic acid that is propane-1,2,3-tricarboxylic acid bearing a hydroxy substituent at position 2. It is an important metabolite in the pathway of all aerobic organisms.	4.42	4	1	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.	5.88	23	1	halide anion; monoatomic chlorine	cofactor; Escherichia coli metabolite; human metabolite
hydrochloric acid Hydrochloric Acid: A strong corrosive acid that is commonly used as a laboratory reagent. It is formed by dissolving hydrogen chloride in water. GASTRIC ACID is the hydrochloric acid component of GASTRIC JUICE.. hydrogen chloride : A mononuclear parent hydride consisting of covalently bonded hydrogen and chlorine atoms.	2.76	3	0	chlorine molecular entity; gas molecular entity; hydrogen halide; mononuclear parent hydride	mouse metabolite
coumarin 2H-chromen-2-one: coumarin derivative	2.5	2	0	coumarins	fluorescent dye; human metabolite; plant metabolite
2-cresol 2-cresol: RN given refers to parent cpd. o-cresol : A cresol that is phenol substituted by a methyl group at position 2. It is a minor urinary metabolite of toluene.	2.04	1	0	cresol	human xenobiotic metabolite
salicylic acid Scalp: The outer covering of the calvaria. It is composed of several layers: SKIN; subcutaneous connective tissue; the occipitofrontal muscle which includes the tendinous galea aponeurotica; loose connective tissue; and the pericranium (the PERIOSTEUM of the SKULL).	13.41	1,259	0	monohydroxybenzoic acid	algal metabolite; antifungal agent; antiinfective agent; EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor; keratolytic drug; plant hormone; plant metabolite
octane Octanes: Eight-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives.. octane : A straight chain alkane composed of 8 carbon atoms.	9.2	5	0	alkane	xenobiotic
phloroglucinol Phloroglucinol: A trinitrobenzene derivative with antispasmodic properties that is used primarily as a laboratory reagent.. phloroglucinol : A benzenetriol with hydroxy groups at position 1, 3 and 5.	3.56	8	0	benzenetriol; phenolic donor	algal metabolite
4-methylumbelliferyl acetate 4-methylumbelliferyl acetate : An acetate ester consiting of umbelliferone carrying a 7-O-acetyl group.	2	1	0	acetate ester; coumarins	plant metabolite
gallic acid gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.	2.9	3	0	trihydroxybenzoic acid	antineoplastic agent; antioxidant; apoptosis inducer; astringent; cyclooxygenase 2 inhibitor; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; geroprotector; human xenobiotic metabolite; plant metabolite
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.	4.37	5	0	gas molecular entity; hydracid; mononuclear parent hydride; sulfur hydride	Escherichia coli metabolite; genotoxin; metabolite; signalling molecule; toxin; vasodilator agent
nornicotine nornicotine: agricultural or horticultural insecticide; RN given refers to (+-)-isomer; structure	2.76	3	0
guaiacol Guaiacol: An agent thought to have disinfectant properties and used as an expectorant. (From Martindale, The Extra Pharmacopoeia, 30th ed, p747). methylcatechol : Any member of the class of catechols carrying one or more methyl substituents.. guaiacol : A monomethoxybenzene that consists of phenol with a methoxy substituent at the ortho position.	2.78	3	0	guaiacols	disinfectant; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; expectorant; plant metabolite
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.	2.44	2	0	2-hydroxydicarboxylic acid; C4-dicarboxylic acid	food acidity regulator; fundamental metabolite
propionaldehyde propionaldehyde: may cause respiratory irritation; RN given refers to parent cpd; structure. propanal : An aldehyde that consists of ethane bearing a formyl substituent. The parent of the class of propanals.	2.05	1	0	alpha-CH2-containing aldehyde; propanals	Escherichia coli metabolite
1-aminocyclopropane-1-carboxylic acid 1-aminocyclopropanecarboxylic acid : A non-proteinogenic alpha-amino acid consisting of cyclopropane having amino and carboxy substituents both at the 1-position.	6.01	34	0	amino acid zwitterion; monocarboxylic acid; non-proteinogenic alpha-amino acid	ethylene releasers; plant metabolite
4-nitrobenzaldehyde 4-nitrobenzaldehyde: RN given refers to parent cpd. 4-nitrobenzaldehyde : A C-nitro compound that is benzaldehyde substituted at the para-position with a nitro group.	2.45	2	0	benzaldehydes; C-nitro compound
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.	2.05	1	0	catechols; dihydroxyphenylacetic acid	human metabolite
aminocaproic acid Aminocaproic Acid: An antifibrinolytic agent that acts by inhibiting plasminogen activators which have fibrinolytic properties.. 6-aminohexanoic acid : An epsilon-amino acid comprising hexanoic acid carrying an amino substituent at position C-6. Used to control postoperative bleeding, and to treat overdose effects of the thrombolytic agents streptokinase and tissue plasminogen activator.	2.03	1	0	amino acid zwitterion; epsilon-amino acid; omega-amino fatty acid	antifibrinolytic drug; hematologic agent; metabolite
dibenzofuran Dibenzofurans: Compounds that include the structure of dibenzofuran.. dibenzofurans : Any organic heterotricyclic compound based on a dibenzofuran skeleton and its substituted derivatives thereof.. dibenzofuran : A mancude organic heterotricyclic parent that consists of a furan ring flanked by two benzene rings ortho-fused across the 2,3- and 4,5-positions.	5.17	2	1	dibenzofurans; mancude organic heterotricyclic parent; polycyclic heteroarene	xenobiotic
fosmidomycin fosmidomycin: from Streptomyces lavendulae; RN given refers to parent cpd; structure in second source. fosmidomycin : Propylphosphonic acid in which one of the hydrogens at position 3 is substituted by a formyl(hydroxy)amino group. An antibiotic obtained from Streptomyces lavendulae, it specifically inhibits DXP reductoisomerase (EC 1.1.1.267), a key enzyme in the non-mevalonate pathway of isoprenoid biosynthesis.	2.44	2	0	hydroxamic acid; phosphonic acids	antimicrobial agent; bacterial metabolite; EC 1.1.1.267 (1-deoxy-D-xylulose-5-phosphate reductoisomerase) inhibitor
cytosine [no description available]	2.07	1	0	aminopyrimidine; pyrimidine nucleobase; pyrimidone	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
lactic acid Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.	2.73	3	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.	5.27	16	0	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
ethanolamine [no description available]	1.98	1	0	ethanolamines; primary alcohol; primary amine	Escherichia coli metabolite; human metabolite; mouse metabolite
formaldehyde paraform: polymerized formaldehyde; RN given refers to parent cpd; used in root canal therapy	3.11	5	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
glycine [no description available]	8.09	44	1	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
glyceraldehyde Glyceraldehyde: An aldotriose containing the propionaldehyde structure with hydroxy groups at the 2- and 3-positions. It is involved in the formation of ADVANCED GLYCOSYLATION END PRODUCTS.. glyceraldehyde : An aldotriose comprising propanal having hydroxy groups at the 2- and 3-positions. It plays role in the formation of advanced glycation end-products (AGEs), a deleterious accompaniment to ageing.. aldose : Aldehydic parent sugars (polyhydroxy aldehydes H[CH(OH)]nC(=O)H, n >= 2) and their intramolecular hemiacetals.	3.11	1	0	aldotriose	fundamental metabolite
glyceric acid glyceric acid: found in urine of patient with D-glyceric acidemia & hyperglycinaemia; RN given refers to parent cpd without isomeric designation. glycerol ether : Any ether having glyceryl as at least one of the O-substituents.. glyceric acid : A trionic acid that consists of propionic acid substituted at positions 2 and 3 by hydroxy groups.	2.03	1	0	trionic acid	fundamental metabolite
glycerol Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.	3.36	7	0	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
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.	2.02	1	0	2-hydroxy monocarboxylic acid; primary alcohol	keratolytic drug; metabolite
carbonic acid Carbonic Acid: Carbonic acid (H2C03). The hypothetical acid of carbon dioxide and water. It exists only in the form of its salts (carbonates), acid salts (hydrogen carbonates), amines (carbamic acid), and acid chlorides (carbonyl chloride). (From Grant & Hackh's Chemical Dictionary, 5th ed)	6.92	1	0	carbon oxoacid; chalcocarbonic acid	mouse metabolite
hydrogen cyanide Hydrogen Cyanide: Hydrogen cyanide (HCN); A toxic liquid or colorless gas. It is found in the smoke of various tobacco products and released by combustion of nitrogen-containing organic materials.. hydrogen cyanide : A one-carbon compound consisting of a methine group triple bonded to a nitrogen atom	2.1	1	0	hydracid; one-carbon compound	Escherichia coli metabolite; human metabolite; poison
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.	4.28	4	1	carbon oxoanion	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
histamine [no description available]	3.96	14	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.	5.68	25	0	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
hydroquinone [no description available]	2.42	2	0	benzenediol; hydroquinones	antioxidant; carcinogenic agent; cofactor; Escherichia coli metabolite; human xenobiotic metabolite; mouse metabolite; skin lightening agent
hydroxylamine amino alcohol : An alcohol containing an amino functional group in addition to the alcohol-defining hydroxy group.	2.02	1	0	hydroxylamines	algal metabolite; bacterial xenobiotic metabolite; EC 1.1.3.13 (alcohol oxidase) inhibitor; EC 4.2.1.22 (cystathionine beta-synthase) inhibitor; EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor; nitric oxide donor; nucleophilic reagent
imidazole imidazole: RN given refers to parent cpd. 1H-imidazole : An imidazole tautomer which has the migrating hydrogen at position 1.	3.12	5	0	imidazole
indole [no description available]	3.87	11	0	indole; polycyclic heteroarene	Escherichia coli metabolite
indoleacetic acid indoleacetic acid: RN given refers to unlabeled parent cpd; structure in Merck Index, 9th ed, #4841. auxin : Any of a group of compounds, both naturally occurring and synthetic, that induce cell elongation in plant stems (from Greek alphaupsilonxialphanuomega, "to grow").. indole-3-acetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group.	6.98	88	0	indole-3-acetic acids; monocarboxylic acid	auxin; human metabolite; mouse metabolite; plant hormone; plant metabolite
iodine Iodine: A nonmetallic element of the halogen group that is represented by the atomic symbol I, atomic number 53, and atomic weight of 126.90. It is a nutritionally essential element, especially important in thyroid hormone synthesis. In solution, it has anti-infective properties and is used topically.. diiodine : Molecule comprising two covalently bonded iodine atoms with overall zero charge..	3.77	3	0	diatomic iodine	nutrient
dihydroxyphenylalanine Dihydroxyphenylalanine: A beta-hydroxylated derivative of phenylalanine. The D-form of dihydroxyphenylalanine has less physiologic activity than the L-form and is commonly used experimentally to determine whether the pharmacological effects of LEVODOPA are stereospecific.. dopa : A hydroxyphenylalanine carrying hydroxy substituents at positions 3 and 4 of the benzene ring.	2.86	4	0	hydroxyphenylalanine; non-proteinogenic alpha-amino acid; tyrosine derivative	human metabolite
pipecolic acid pipecolic acid: RN given refers to cpd without isomeric designation. pipecolic acid : A piperidinemonocarboxylic acid in which the carboxy group is located at position C-2.. pipecolate : A piperidinecarboxylate that is the conjugate base of pipecolic acid.	3.93	3	0	piperidinemonocarboxylic acid
2,3,4,5-tetrahydroxypentanal [no description available]	2.13	1	0	hydroxyaldehyde; pentose; polyol
thioctic acid Thioctic Acid: An octanoic acid bridged with two sulfurs so that it is sometimes also called a pentanoic acid in some naming schemes. It is biosynthesized by cleavage of LINOLEIC ACID and is a coenzyme of oxoglutarate dehydrogenase (KETOGLUTARATE DEHYDROGENASE COMPLEX). It is used in DIETARY SUPPLEMENTS.	1.94	1	0	dithiolanes; heterocyclic fatty acid; thia fatty acid	fundamental metabolite; geroprotector
pyruvaldehyde Pyruvaldehyde: An organic compound used often as a reagent in organic synthesis, as a flavoring agent, and in tanning. It has been demonstrated as an intermediate in the metabolism of acetone and its derivatives in isolated cell preparations, in various culture media, and in vivo in certain animals.. methylglyoxal : A 2-oxo aldehyde derived from propanal.	2.8	3	0	2-oxo aldehyde; propanals	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
methanol Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.	5.91	31	0	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
phytic acid Phytic Acid: Complexing agent for removal of traces of heavy metal ions. It acts also as a hypocalcemic agent.. myo-inositol hexakisphosphate : A myo-inositol hexakisphosphate in which each hydroxy group of myo-inositol is monophosphorylated.	2.52	2	0	inositol phosphate
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.	3.5	8	0	cyclitol; hexol
melatonin [no description available]	6.98	11	1	acetamides; tryptamines	anticonvulsant; central nervous system depressant; geroprotector; hormone; human metabolite; immunological adjuvant; mouse metabolite; radical scavenger
croton oil [no description available]	2.04	1	0	N-acyl-hexosamine
naphthalene [no description available]	3.25	6	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.	10.47	20	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.	2.46	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
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	3.93	12	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
nitric acid Nitric Acid: Nitric acid (HNO3). A colorless liquid that is used in the manufacture of inorganic and organic nitrates and nitro compounds for fertilizers, dye intermediates, explosives, and many different organic chemicals. Continued exposure to vapor may cause chronic bronchitis; chemical pneumonitis may occur. (From Merck Index, 11th ed). nitric acid : A nitrogen oxoacid of formula HNO3 in which the nitrogen atom is bonded to a hydroxy group and by equivalent bonds to the remaining two oxygen atoms.	2.03	1	0	nitrogen oxoacid	protic solvent; reagent
nitrites Nitrites: Salts of nitrous acid or compounds containing the group NO2-. The inorganic nitrites of the type MNO2 (where M=metal) are all insoluble, except the alkali nitrites. The organic nitrites may be isomeric, but not identical with the corresponding nitro compounds. (Grant & Hackh's Chemical Dictionary, 5th ed)	2.74	3	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.	2.02	1	0	octanol; primary alcohol	antifungal agent; bacterial metabolite; fuel additive; kairomone; plant metabolite
orotic acid Orotic Acid: An intermediate product in PYRIMIDINE synthesis which plays a role in chemical conversions between DIHYDROFOLATE and TETRAHYDROFOLATE.. orotic acid : A pyrimidinemonocarboxylic acid that is uracil bearing a carboxy substituent at position C-6.	2.42	2	0	pyrimidinemonocarboxylic acid	Escherichia coli metabolite; metabolite; mouse metabolite
oxalic acid Oxalic Acid: A strong dicarboxylic acid occurring in many plants and vegetables. It is produced in the body by metabolism of glyoxylic acid or ascorbic acid. It is not metabolized but excreted in the urine. It is used as an analytical reagent and general reducing agent.. oxalic acid : An alpha,omega-dicarboxylic acid that is ethane substituted by carboxyl groups at positions 1 and 2.	3.18	5	0	alpha,omega-dicarboxylic acid	algal metabolite; human metabolite; plant metabolite
4-aminobenzoic acid 4-Aminobenzoic Acid: An aminobenzoic acid isomer that combines with pteridine and GLUTAMIC ACID to form FOLIC ACID. The fact that 4-aminobenzoic acid absorbs light throughout the UVB range has also resulted in its use as an ingredient in SUNSCREENS.. 4-ammoniobenzoate : A zwitterion obtained by transfer of a proton from the carboxy to the amino group of 4-aminobenzoic acid.. 4-aminobenzoic acid : An aminobenzoic acid in which the amino group is para to the carboxy group.	2.5	2	0	aminobenzoic acid; aromatic amino-acid zwitterion	allergen; Escherichia coli metabolite; plant metabolite
4-hydroxyphenylpyruvic acid 4-hydroxyphenylpyruvic acid: RN given refers to parent cpd. 4-hydroxyphenylpyruvic acid : A 2-oxo monocarboxylic acid that is pyruvic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group.	2.01	1	0	2-oxo monocarboxylic acid; phenols	human metabolite
palmitic acid Palmitic Acid: A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids.. hexadecanoic acid : A straight-chain, sixteen-carbon, saturated long-chain fatty acid.	3.88	12	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
phenanthrene phenanthrene : A polycyclic aromatic hydrocarbon composed of three fused benzene rings which takes its name from the two terms 'phenyl' and 'anthracene.'	2.48	2	0	ortho-fused polycyclic arene; ortho-fused tricyclic hydrocarbon; phenanthrenes	environmental contaminant; mouse metabolite
phenol [no description available]	3.17	5	0	phenols	antiseptic drug; disinfectant; human xenobiotic metabolite; mouse metabolite
phenylacetaldehyde [no description available]	2.06	1	0	alpha-CH2-containing aldehyde; phenylacetaldehydes	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
phenylacetic acid phenylacetic acid : A monocarboxylic acid that is toluene in which one of the hydrogens of the methyl group has been replaced by a carboxy group.	2.52	2	0	benzenes; monocarboxylic acid; phenylacetic acids	allergen; Aspergillus metabolite; auxin; EC 6.4.1.1 (pyruvate carboxylase) inhibitor; Escherichia coli metabolite; human metabolite; plant growth retardant; plant metabolite; Saccharomyces cerevisiae metabolite; toxin
phenethylamine phenethylamine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7016. 2-phenylethylamine : A phenylethylamine having the phenyl substituent at the 2-position.	2.11	1	0	alkaloid; aralkylamine; phenylethylamine	Escherichia coli metabolite; human metabolite; mouse metabolite
phosphoric acid phosphoric acid: concise etchant is 37% H3PO4. phosphoric acid : A phosphorus oxoacid that consists of one oxo and three hydroxy groups joined covalently to a central phosphorus atom.	2.31	1	0	phosphoric acids	algal metabolite; fertilizer; human metabolite; NMR chemical shift reference compound; solvent
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.	2.02	1	0	carboxyalkyl phosphate; monocarboxylic acid	fundamental metabolite
phosphorylcholine Phosphorylcholine: Calcium and magnesium salts used therapeutically in hepatobiliary dysfunction.. phosphocholine : The phosphate of choline; and the parent compound of the phosphocholine family.	2.73	3	0	phosphocholines	allergen; epitope; hapten; human metabolite; mouse metabolite
picolinic acid picolinic acid: iron-chelating agent that inhibits DNA synthesis; may interfere with iron-dependent production of stable free organic radical which is essential for ribonucleotide reductase formation of deoxyribonucleotides; RN given refers to parent cpd; structure in Merck Index, 9th ed, #7206. picolinic acid : A pyridinemonocarboxylic acid in which the carboxy group is located at position 2. It is an intermediate in the metabolism of tryptophan.	2.05	1	0	pyridinemonocarboxylic acid	human metabolite; MALDI matrix material
1-propanol 1-Propanol: A colorless liquid made by oxidation of aliphatic hydrocarbons that is used as a solvent and chemical intermediate.. propan-1-ol : The parent member of the class of propan-1-ols that is propane in which a hydrogen of one of the methyl groups is replaced by a hydroxy group.	3.21	6	0	propan-1-ols; short-chain primary fatty alcohol	metabolite; protic solvent
propionic acid propionic acid : A short-chain saturated fatty acid comprising ethane attached to the carbon of a carboxy group.	2.01	1	0	saturated fatty acid; short-chain fatty acid	antifungal drug
pteridines [no description available]	1.96	1	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; pteridines
purine 1H-purine : The 1H-tautomer of purine.. 3H-purine : The 3H-tautomer of purine.. 9H-purine : The 9H-tautomer of purine.. 7H-purine : The 7H-tautomer of purine.	2.69	3	0	purine
putrescine [no description available]	4.26	17	0	alkane-alpha,omega-diamine	antioxidant; fundamental metabolite
pyrazole 1H-pyrazole : The 1H-tautomer of pyrazole.	2.01	1	0	pyrazole
pyridine azine : An organonitrogen compound of general structure RCH=N-N=CHR or RR'C=N-N=CRR'.	3.3	6	0	azaarene; mancude organic heteromonocyclic parent; monocyclic heteroarene; pyridines	environmental contaminant; NMR chemical shift reference compound
pyridoxal phosphate Pyridoxal Phosphate: This is the active form of VITAMIN B 6 serving as a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into pyridoxamine phosphate (PYRIDOXAMINE).. pyridoxal 5'-phosphate : The monophosphate ester obtained by condensation of phosphoric acid with the primary hydroxy group of pyridoxal.	2.37	2	0	methylpyridines; monohydroxypyridine; pyridinecarbaldehyde; vitamin B6 phosphate	coenzyme; cofactor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
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).	2.88	4	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.	2.41	1	0	benzenetriol; phenolic donor	plant metabolite
quinolinic acid Quinolinic Acid: A metabolite of tryptophan with a possible role in neurodegenerative disorders. Elevated CSF levels of quinolinic acid are correlated with the severity of neuropsychological deficits in patients who have AIDS.. pyridinedicarboxylic acid : Any member of the class of pyridines carrying two carboxy groups.. quinolinic acid : A pyridinedicarboxylic acid that is pyridine substituted by carboxy groups at positions 2 and 3. It is a metabolite of tryptophan.	1.99	1	0	pyridinedicarboxylic acid	Escherichia coli metabolite; human metabolite; mouse metabolite; NMDA receptor agonist
dimethyl sulfide dimethyl sulfide: structure. dimethyl sulfide : A methyl sulfide in which the sulfur atom is substituted by two methyl groups. It is produced naturally by some marine algae.. methyl sulfide : Any aliphatic sulfide in which at least one of the organyl groups attached to the sulfur is a methyl group.	2.04	1	0	aliphatic sulfide	algal metabolite; bacterial xenobiotic metabolite; EC 3.5.1.4 (amidase) inhibitor; Escherichia coli metabolite; marine metabolite
selenic acid Selenic Acid: A strong dibasic acid with the molecular formula H2SeO4. Included under this heading is the acid form, and inorganic salts of dihydrogen selenium tetraoxide.	3.1	4	0	selenium oxoacid
sulfites Sulfites: Inorganic salts of sulfurous acid.. sulfites : Any sulfurous acid derivative that is a salt or an ester of sulfurous acid.. organosulfonate oxoanion : An organic anion obtained by deprotonation of the sufonate group(s) of any organosulfonic acid.. sulfite : A sulfur oxoanion that is the conjugate base of hydrogen sulfite (H2SO3).	2.01	1	0	divalent inorganic anion; sulfur oxide; sulfur oxoanion
spermidine [no description available]	5.06	9	1	polyazaalkane; triamine	autophagy inducer; fundamental metabolite; geroprotector
spermine [no description available]	5.22	15	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.	6.92	1	0	alpha,omega-dicarboxylic acid; C4-dicarboxylic acid	anti-ulcer drug; fundamental metabolite; micronutrient; nutraceutical; radiation protective agent
sulfur dioxide Sulfur Dioxide: A highly toxic, colorless, nonflammable gas. It is used as a pharmaceutical aid and antioxidant. It is also an environmental air pollutant.	2.46	2	0	sulfur oxide	Escherichia coli metabolite; food bleaching agent; refrigerant
taurine [no description available]	3.88	12	0	amino sulfonic acid; zwitterion	antioxidant; Escherichia coli metabolite; glycine receptor agonist; human metabolite; mouse metabolite; nutrient; radical scavenger; Saccharomyces cerevisiae metabolite
thiophane [no description available]	2.13	1	0	saturated organic heteromonocyclic parent; tetrahydrothiophenes
thiamine thiamine(1+) : A primary alcohol that is 1,3-thiazol-3-ium substituted by (4-amino-2-methylpyrimidin-5-yl)methyl, methyl and 2-hydroxyethyl groups at positions 3, 4 and 5, respectively.	2.04	1	0	primary alcohol; vitamin B1	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
thymine [no description available]	2.44	2	0	pyrimidine nucleobase; pyrimidone	Escherichia coli metabolite; human metabolite; mouse metabolite
toluene methylbenzene : Any alkylbenzene that is benzene substituted with one or more methyl groups.	3.51	8	0	methylbenzene; toluenes; volatile organic compound	cholinergic antagonist; fuel additive; neurotoxin; non-polar solvent
tryptamine [no description available]	3.58	2	0	aminoalkylindole; aralkylamino compound; indole alkaloid; tryptamines	human metabolite; mouse metabolite; plant metabolite
uracil 2,4-dihydroxypyrimidine: a urinary biomarker for bipolar disorder	8.06	5	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.	3.33	1	1	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.	10.27	12	1	isourea; monocarboxylic acid amide; one-carbon compound	Daphnia magna metabolite; Escherichia coli metabolite; fertilizer; flour treatment agent; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
vanillin Vanilla: A plant genus of the family ORCHIDACEAE that is the source of the familiar flavoring used in foods and medicines (FLAVORING AGENTS).	3.02	4	0	benzaldehydes; monomethoxybenzene; phenols	anti-inflammatory agent; anticonvulsant; antioxidant; flavouring agent; plant metabolite
2-amino-5-phosphonovalerate 2-Amino-5-phosphonovalerate: The D-enantiomer is a potent and specific antagonist of NMDA glutamate receptors (RECEPTORS, N-METHYL-D-ASPARTATE). The L form is inactive at NMDA receptors but may affect the AP4 (2-amino-4-phosphonobutyrate; APB) excitatory amino acid receptors.	3.09	5	0	non-proteinogenic alpha-amino acid	NMDA receptor antagonist
7-hydroxy-2-n,n-dipropylaminotetralin 7-hydroxy-2-N,N-dipropylaminotetralin: RN given refers to cpd without isomeric designation	1.98	1	0	tetralins
8-hydroxy-2-(di-n-propylamino)tetralin 8-Hydroxy-2-(di-n-propylamino)tetralin: A serotonin 1A-receptor agonist that is used experimentally to test the effects of serotonin.. 8-OH-DPAT : A tetralin substituted at positions 1 and 7 by hydroxy and dipropylamino groups respectively	2.05	1	0	phenols; tertiary amino compound; tetralins	serotonergic antagonist
alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid: An IBOTENIC ACID homolog and glutamate agonist. The compound is the defining agonist for the AMPA subtype of glutamate receptors (RECEPTORS, AMPA). It has been used as a radionuclide imaging agent but is more commonly used as an experimental tool in cell biological studies.	4.48	5	1	non-proteinogenic alpha-amino acid
3-(2-carboxypiperazin-4-yl)propyl-1-phosphonic acid 3-(2-carboxypiperazin-4-yl)propyl-1-phosphonic acid: structure given in first source; NMDA receptor antagonist	1.99	1	0
4-iodo-2,5-dimethoxyphenylisopropylamine 4-iodo-2,5-dimethoxyphenylisopropylamine: RN given refers to unlabeled parent cpd without isomeric designation; a serotonin agonist. 2-(4-iodo-2,5-dimethoxyphenyl)-1-methylethylamine : An organoiodine compound that is amphetamine bearing two methoxy substituents at positions 2 and 5 as well as an iodo substituent at position 4.	2.04	1	0	amphetamines; dimethoxybenzene; organoiodine compound
1-hydroxy-3-amino-2-pyrrolidone 1-hydroxy-3-amino-2-pyrrolidone: a CNS depressant; structure in first source	2.01	1	0
ibotenic acid Ibotenic Acid: A neurotoxic isoxazole (similar to KAINIC ACID and MUSCIMOL) found in AMANITA mushrooms. It causes motor depression, ataxia, and changes in mood, perceptions and feelings, and is a potent excitatory amino acid agonist.	1.98	1	0	non-proteinogenic alpha-amino acid	neurotoxin
menthol Menthol: A monoterpene cyclohexanol produced from mint oils.	3.11	5	0	p-menthane monoterpenoid; secondary alcohol	volatile oil component
1,10-phenanthroline 1,10-phenanthroline: RN given refers to parent cpd; inhibits Zn-dependent metalloproteinases	2.45	2	0	phenanthroline	EC 2.7.1.1 (hexokinase) inhibitor; EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor
1,2-dioctanoylglycerol 1,2-dioctanoylglycerol: functions as bioregulator of protein kinase C in human platelets	1.97	1	0
1,3-dipropyl-8-cyclopentylxanthine DPCPX : An oxopurine that is 7H-xanthine substituted at positions 1 and 3 by propyl groups and at position 8 by a cyclohexyl group.	2.46	2	0	oxopurine	adenosine A1 receptor antagonist; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor
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.	5.75	26	0	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
1-methylimidazole 1-methyl-1H-imidazole : A 1H-imidazole having a methyl substituent at the N-1 position.	2.05	1	0	imidazoles
edelfosine edelfosine: RN given refers to parent cpd. edelfosine : A racemate comprising equimolar amounts of (R)- and (S)-edelfosine.. 1-octadecyl-2-methylglycero-3-phosphocholine : A glycerophosphocholine that is glycero-3-phosphocholine substituted at positions 1 and 2 by octadecyl and methyl groups respectively.	2.08	1	0	glycerophosphocholine
2,2'-dipyridyl 2,2'-Dipyridyl: A reagent used for the determination of iron.. 2,2'-bipyridine : A bipyridine in which the two pyridine moieties are linked by a bond between positions C-2 and C-2'.	3.53	8	0	bipyridine	chelator; ferroptosis inhibitor
2,4-dichlorophenoxyacetic acid 2,4-Dichlorophenoxyacetic Acid: An herbicide with irritant effects on the eye and the gastrointestinal system.. 2,4-D : A chlorophenoxyacetic acid that is phenoxyacetic acid in which the ring hydrogens at postions 2 and 4 are substituted by chlorines.	3.9	12	0	chlorophenoxyacetic acid; dichlorobenzene	agrochemical; defoliant; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; environmental contaminant; phenoxy herbicide; synthetic auxin
2,4-dinitrophenol 2,4-Dinitrophenol: A toxic dye, chemically related to trinitrophenol (picric acid), used in biochemical studies of oxidative processes where it uncouples oxidative phosphorylation. It is also used as a metabolic stimulant. (Stedman, 26th ed). dinitrophenol : Members of the class of nitrophenol carrying two nitro substituents.. 2,4-dinitrophenol : A dinitrophenol having the nitro groups at the 2- and 4-positions.	2.92	4	0	dinitrophenol	allergen; antiseptic drug; bacterial xenobiotic metabolite; geroprotector; oxidative phosphorylation inhibitor
2-hydroxysaclofen 2-hydroxysaclofen: structure given in first source	2.05	1	0	organochlorine compound
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.	3.07	5	0	alkanethiol; primary alcohol	geroprotector
amitrole Amitrole: A non-selective post-emergence, translocated herbicide. According to the Seventh Annual Report on Carcinogens (PB95-109781, 1994) this substance may reasonably be anticipated to be a carcinogen. (From Merck Index, 12th ed) It is an irreversible inhibitor of CATALASE, and thus impairs activity of peroxisomes.. amitrole : A member of the class of triazoles that is 1H-1,2,4-triazole substituted by an amino group at position 3. Used to control annual grasses and aquatic weeds (but not on food crops because it causes cancer in laboratory animals). Its use within the EU was banned from September 2017 on the grounds of potential groundwater contamination and risks to aquatic life; there have also been concerns about its endocrine-disrupting properties.	2.44	2	0	aromatic amine; triazoles	carotenoid biosynthesis inhibitor; EC 1.11.1.6 (catalase) inhibitor; herbicide
3-methylcholanthrene Methylcholanthrene: A carcinogen that is often used in experimental cancer studies.. 3-methylcholanthrene : A pentacyclic ortho- and peri-fused polycyclic arene consisting of a dihydrocyclopenta[ij]tetraphene ring system with a methyl substituent at the 3-position.	2.66	3	0	ortho- and peri-fused polycyclic arene	aryl hydrocarbon receptor agonist; carcinogenic agent
3-nitrobenzeneboronic acid [no description available]	2.02	1	0
3-nitropropionic acid 3-nitropropionic acid: succinate dehydrogenase inactivator; biosynthesized by FABACEAE plants from ASPARAGINE. 3-nitropropanoic acid : A C-nitro compound that is propanoic acid in which one of the methyl hydrogens has been replaced by a nitro group.	1.99	1	0	C-nitro compound	antimycobacterial drug; EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor; mycotoxin; neurotoxin
4-aminopyridine [no description available]	2.03	1	0	aminopyridine; aromatic amine	avicide; orphan drug; potassium channel blocker
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.	2.05	1	0	guaiacols; monocarboxylic acid	human metabolite; mouse metabolite
phenytoin [no description available]	4.32	6	0	imidazolidine-2,4-dione	anticonvulsant; drug allergen; sodium channel blocker; teratogenic agent
5,8,11,14-eicosatetraynoic acid 5,8,11,14-Eicosatetraynoic Acid: A 20-carbon unsaturated fatty acid containing 4 alkyne bonds. It inhibits the enzymatic conversion of arachidonic acid to prostaglandins E(2) and F(2a).	2.71	3	0	long-chain fatty acid
8-(4-sulfophenyl)theophylline 8-(4-sulfophenyl)theophylline: adenosine antagonist	1.98	1	0
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.	2.6	1	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)	2.35	2	0	monocarboxylic acid amide; sulfonamide; thiadiazoles	anticonvulsant; diuretic; EC 4.2.1.1 (carbonic anhydrase) inhibitor
aluminum fluoride [no description available]	3.77	11	0	aluminium coordination entity
amantadine amant: an antiviral compound consisting of an adamantane derivative chemically linked to a water-solube polyanioic matrix; structure in first source	5.82	9	0	adamantanes; primary aliphatic amine	analgesic; antiparkinson drug; antiviral drug; dopaminergic agent; NMDA receptor antagonist; non-narcotic analgesic
theophylline [no description available]	3.46	8	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
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.	1.97	1	0	carbotricyclic compound; tertiary amine	adrenergic uptake inhibitor; antidepressant; environmental contaminant; tropomyosin-related kinase B receptor agonist; xenobiotic
amsacrine Amsacrine: An aminoacridine derivative that intercalates into DNA and is used as an antineoplastic agent.. amsacrine : A sulfonamide that is N-phenylmethanesulfonamide substituted by a methoxy group at position 3 and an acridin-9-ylamino group at position 4. It exhibits antineoplastic activity.	1.98	1	0	acridines; aromatic ether; sulfonamide	antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
2-amino-4-phosphonobutyric acid 2-amino-4-phosphonobutyric acid: glutamate antagonist in locust muscle; structure; do not confuse with L-AP4, which is the propionic acid version	3.1	5	0
arecoline Arecoline: An alkaloid obtained from the betel nut (Areca catechu), fruit of a palm tree. It is an agonist at both muscarinic and nicotinic acetylcholine receptors. It is used in the form of various salts as a ganglionic stimulant, a parasympathomimetic, and a vermifuge, especially in veterinary practice. It has been used as a euphoriant in the Pacific Islands.. arecoline : A tetrahydropyridine that is 1,2,5,6-tetrahydropyridine with a methyl group at position 1, and a methoxycarbonyl group at position 3. An alkaloid found in the areca nut, it acts as an agonist of muscarinic acetylcholine.	2.35	2	0	enoate ester; methyl ester; pyridine alkaloid; tetrahydropyridine	metabolite; muscarinic agonist
aristolochic acid i aristolochic acid I: phospholipase A inhibitor. aristolochic acid A : An aristolochic acid that is phenanthrene-1-carboxylic acid that is substituted by a methylenedioxy group at the 3,4 positions, by a methoxy group at position 8, and by a nitro group at position 10. It is the most abundant of the aristolochic acids and is found in almost all Aristolochia (birthworts or pipevines) species. It has been tried in a number of treatments for inflammatory disorders, mainly in Chinese and folk medicine. However, there is concern over their use as aristolochic acid is both carcinogenic and nephrotoxic.	2.43	2	0	aristolochic acids; aromatic ether; C-nitro compound; cyclic acetal; monocarboxylic acid; organic heterotetracyclic compound	carcinogenic agent; metabolite; mutagen; nephrotoxin; toxin
aspirin Aspirin: The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5). acetylsalicylate : A benzoate that is the conjugate base of acetylsalicylic acid, arising from deprotonation of the carboxy group.. acetylsalicylic acid : A member of the class of benzoic acids that is salicylic acid in which the hydrogen that is attached to the phenolic hydroxy group has been replaced by an acetoxy group. A non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity.	4.8	10	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.	2.15	1	0	benzimidazoles; piperidines	anti-allergic agent; anticoronaviral agent; H1-receptor antagonist
atrazine [no description available]	2.31	1	0	chloro-1,3,5-triazine; diamino-1,3,5-triazine	environmental contaminant; herbicide; xenobiotic
azathioprine Azathioprine: An immunosuppressive agent used in combination with cyclophosphamide and hydroxychloroquine in the treatment of rheumatoid arthritis. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), this substance has been listed as a known carcinogen. (Merck Index, 11th ed). azathioprine : A thiopurine that is 6-mercaptopurine in which the mercapto hydrogen is replaced by a 1-methyl-4-nitroimidazol-5-yl group. It is a prodrug for mercaptopurine and is used as an immunosuppressant, prescribed for the treatment of inflammatory conditions and after organ transplantation and also for treatment of Crohn's didease and MS.	2.64	3	0	aryl sulfide; C-nitro compound; imidazoles; thiopurine	antimetabolite; antineoplastic agent; carcinogenic agent; DNA synthesis inhibitor; hepatotoxic agent; immunosuppressive agent; prodrug
azelaic acid nonanedioic acid : An alpha,omega-dicarboxylic acid that is heptane substituted at positions 1 and 7 by carboxy groups.	4.1	4	0	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	antibacterial agent; antineoplastic agent; dermatologic drug; plant metabolite
azobenzene azobenzene: photosensor molecule known to undergo reversible isomerization from trans to cis on illumination with photons of appropriate wavelength; RN given refers to cpd without isomeric designation; structure. (E)-azobenzene : The (E)-isomer of azobenzene.. (Z)-azobenzene : The (Z)-isomer of azobenzene.. azobenzene : A molecule whose structure comprises two phenyl rings linked by a N=N double bond; the parent compound of the azobenzene class of compounds.	3.59	2	0	azobenzenes
baclofen [no description available]	5.92	18	0	amino acid zwitterion; gamma-amino acid; monocarboxylic acid; monochlorobenzenes; primary amino compound	central nervous system depressant; GABA agonist; muscle relaxant
benzo(a)pyrene Benzo(a)pyrene: A potent mutagen and carcinogen. It is a public health concern because of its possible effects on industrial workers, as an environmental pollutant, an as a component of tobacco smoke.. benzo[a]pyrene : An ortho- and peri-fused polycyclic arene consisting of five fused benzene rings.	5.41	4	1	ortho- and peri-fused polycyclic arene	carcinogenic agent; mouse metabolite
benzothiazide benzothiazide: structure. benzthiazide : 7-Sulfamoyl-1,2,4-benzothiadiazine 1,1-dioxide in which the hydrogen at position 6 is substituted by chlorine and that at position 3 is substituted by a benzylsulfanylmethyl group. A diuretic, it is used to treat hypertension and edema.	2.76	3	0	benzothiadiazine; sulfonamide	antihypertensive agent; diuretic
bepridil Bepridil: A long-acting calcium-blocking agent with significant anti-anginal activity. The drug produces significant coronary vasodilation and modest peripheral effects. It has antihypertensive and selective anti-arrhythmia activities and acts as a calmodulin antagonist.. bepridil : A tertiary amine in which the substituents on nitrogen are benzyl, phenyl and 3-(2-methylpropoxy)-2-(pyrrolidin-1-yl)propyl.	2	1	0	pyrrolidines; tertiary amine	anti-arrhythmia drug; antihypertensive agent; calcium channel blocker; vasodilator agent
berberine [no description available]	3.14	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
5-methoxypsoralen 5-Methoxypsoralen: A linear furanocoumarin that has phototoxic and anti-inflammatory properties, with effects similar to METHOXSALEN. It is used in PUVA THERAPY for the treatment of PSORIASIS.. 5-methoxypsoralen : A 5-methoxyfurocoumarin that is psoralen substituted by a methoxy group at position 5.	2.17	1	0	5-methoxyfurocoumarin; organic heterotricyclic compound; psoralens	hepatoprotective agent; plant metabolite
2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one: from maize extracts; structure given in first source. DIMBOA : A lactol that is DIBOA in which the hydrogen at position 7 is replaced by a methoxy group. It has been isolated from the maize plants.	2.48	2	0	aromatic ether; benzoxazine; cyclic hydroxamic acid; lactol	allelochemical; plant metabolite
bicalutamide bicalutamide: approved for treatment of advanced prostate cancer. N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide : A member of the class of (trifluoromethyl)benzenes that is 4-amino-2-(trifluoromethyl)benzonitrile in which one of the amino hydrogens is substituted by a 3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanoyl group.. bicalutamide : A racemate comprising of equal amounts of (R)-bicalutamide and (S)-bicalutamide. It is an oral non-steroidal antiandrogen used in the treatment of prostate cancer and hirsutism.	2.06	1	0	(trifluoromethyl)benzenes; monocarboxylic acid amide; monofluorobenzenes; nitrile; sulfone; tertiary alcohol
biperiden Biperiden: A muscarinic antagonist that has effects in both the central and peripheral nervous systems. It has been used in the treatment of arteriosclerotic, idiopathic, and postencephalitic parkinsonism. It has also been used to alleviate extrapyramidal symptoms induced by phenothiazine derivatives and reserpine.. biperiden : A member of the class of piperidines that is N-propylpiperidine in which the methyl hydrogens have been replaced by hydroxy, phenyl, and 5-norbornen-2-yl groups. A muscarinic antagonist affecting both the central and peripheral nervous systems, it is used in the treatment of all forms of Parkinson's disease.	2.65	3	0	piperidines; tertiary alcohol; tertiary amino compound	antidote to sarin poisoning; antidyskinesia agent; antiparkinson drug; muscarinic antagonist; parasympatholytic
bisbenzimidazole Bisbenzimidazole: A benzimidazole antifilarial agent; it is fluorescent when it binds to certain nucleotides in DNA, thus providing a tool for the study of DNA replication; it also interferes with mitosis.	2.06	1	0	bibenzimidazole; N-methylpiperazine	anthelminthic drug; fluorochrome
bisindolylmaleimide i bisindolylmaleimide I: a bis(indolyl)maleimide	2	1	0
ro 31-7549 Ro 31-7549: structure	1.99	1	0
bretylium bretylium: RN given refers to parent cpd. bretylium : A quaternary ammonium cation having 2-bromobenzyl, ethyl and two methyl groups attached to the nitrogen. It blocks noradrenaline release from the peripheral sympathetic nervous system, and is used in emergency medicine, cardiology, and other specialties for the acute management of ventricular tachycardia and ventricular fibrillation.	1.98	1	0	quaternary ammonium ion	adrenergic antagonist; anti-arrhythmia drug; antihypertensive agent
bumetanide [no description available]	2.45	2	0	amino acid; benzoic acids; sulfonamide	diuretic; EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor
bupivacaine Bupivacaine: A widely used local anesthetic agent.. 1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide : A piperidinecarboxamide obtained by formal condensation of the carboxy group of N-butylpipecolic acid with the amino group of 2,6-dimethylaniline.. bupivacaine : A racemate composed of equimolar amounts of dextrobupivacaine and levobupivacaine. Used (in the form of its hydrochloride hydrate) as a local anaesthetic.	2.17	1	0	aromatic amide; piperidinecarboxamide; tertiary amino compound
caffeine [no description available]	3.29	6	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.	3.5	8	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.	1.98	1	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
camphor, (+-)-isomer [no description available]	3.22	6	0	bornane monoterpenoid; cyclic monoterpene ketone	plant metabolite
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.	2.38	2	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
carbetapentane carbetapentane: RN given refers to parent cpd	9.04	45	1	benzenes
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.	4.77	12	0	hydrazone; monochlorobenzenes; nitrile	antibacterial agent; geroprotector; ionophore
cgp 12177 CGP 12177 : A benzimidazole that is benzimidazol-2-one substituted at position 4 by a 3-(tert-butylamino)-2-hydroxypropoxy group.	2.51	2	0	aromatic ether; benzimidazoles; secondary alcohol; secondary amino compound	beta-adrenergic antagonist
chelerythrine chelerythrine : A benzophenanthridine alkaloid isolated from the root of Zanthoxylum simulans, Chelidonium majus L., and other Papaveraceae.	2.31	1	0	benzophenanthridine alkaloid; organic cation	antibacterial agent; antineoplastic agent; EC 2.7.11.13 (protein kinase C) inhibitor
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.	5.14	46	0	aminoquinoline; organochlorine compound; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; antirheumatic drug; autophagy inhibitor; dermatologic drug
chlorpheniramine Chlorpheniramine: A histamine H1 antagonist used in allergic reactions, hay fever, rhinitis, urticaria, and asthma. It has also been used in veterinary applications. One of the most widely used of the classical antihistaminics, it generally causes less drowsiness and sedation than PROMETHAZINE.. chlorphenamine : A tertiary amino compound that is propylamine which is substituted at position 3 by a pyridin-2-yl group and a p-chlorophenyl group and in which the hydrogens attached to the nitrogen are replaced by methyl groups. A histamine H1 antagonist, it is used to relieve the symptoms of hay fever, rhinitis, urticaria, and asthma.	2.02	1	0	monochlorobenzenes; pyridines; tertiary amino compound	anti-allergic agent; antidepressant; antipruritic drug; H1-receptor antagonist; histamine antagonist; serotonin uptake inhibitor
chlorpromazine Chlorpromazine: The prototypical phenothiazine antipsychotic drug. Like the other drugs in this class chlorpromazine's antipsychotic actions are thought to be due to long-term adaptation by the brain to blocking DOPAMINE RECEPTORS. Chlorpromazine has several other actions and therapeutic uses, including as an antiemetic and in the treatment of intractable hiccup.. chlorpromazine : A substituted phenothiazine in which the ring nitrogen at position 10 is attached to C-3 of an N,N-dimethylpropanamine moiety.	2.03	1	0	organochlorine compound; phenothiazines; tertiary amine	anticoronaviral agent; antiemetic; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; phenothiazine antipsychotic drug
chrysanthemic acid chrysanthemic acid: occurs as esters in pyrethrum flowers; RN given refers to cpd without isomeric designation; structure. chrysanthemic acid : A monocarboxylic acid that is cyclopropanecarboxylic acid substituted by two methyl groups at position 2 and a 2-methylprop-1-en-1-yl group at position 3.	2.02	1	0	cyclopropanes; monocarboxylic acid	plant metabolite
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.	2.71	3	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.	2.36	2	0	aliphatic sulfide; guanidines; imidazoles; nitrile	adjuvant; analgesic; anti-ulcer drug; H2-receptor antagonist; P450 inhibitor
eucalyptol [no description available]	3.01	4	0
platinum tetrachloride platinum chloride: RN given refers to cpd with unspecified MF; structure in first source: K2PtCl; see also platinum tetrachloride. platinum dichloride : A platinum coordination entity consisting of platinum(II) bound to two chlorine atoms.	2.08	1	0	platinum coordination entity	catalyst; reagent
citalopram Citalopram: A furancarbonitrile that is one of the serotonin uptake inhibitors used as an antidepressant. The drug is also effective in reducing ethanol uptake in alcoholics and is used in depressed patients who also suffer from TARDIVE DYSKINESIA in preference to tricyclic antidepressants, which aggravate dyskinesia.. citalopram : A racemate comprising equimolar amounts of (R)-citalopram and its enantiomer, escitalopram. It is used as an antidepressant, although only escitalopram is active.. 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile : A nitrile that is 1,3-dihydro-2-benzofuran-5-carbonitrile in which one of the hydrogens at position 1 is replaced by a p-fluorophenyl group, while the other is replaced by a 3-(dimethylamino)propyl group.	2.03	1	0	2-benzofurans; cyclic ether; nitrile; organofluorine compound; tertiary amino compound
clofazimine Clofazimine: A fat-soluble riminophenazine dye used for the treatment of leprosy. It has been used investigationally in combination with other antimycobacterial drugs to treat Mycobacterium avium infections in AIDS patients. Clofazimine also has a marked anti-inflammatory effect and is given to control the leprosy reaction, erythema nodosum leprosum. (From AMA Drug Evaluations Annual, 1993, p1619). clofazimine : 3-Isopropylimino-3,5-dihydro-phenazine in which the hydrogen at position 5 is substituted substituted by a 4-chlorophenyl group, and that at position 2 is substituted by a (4-chlorophenyl)amino group. A dark red crystalline solid, clofazimine is an antimycobacterial and is one of the main drugs used for the treatment of multi-bacillary leprosy. However, it can cause red/brown discolouration of the skin, so other treatments are often preferred in light-skinned patients.	2.39	2	0	monochlorobenzenes; phenazines	dye; leprostatic drug; non-steroidal anti-inflammatory drug
clofibrate angiokapsul: contains clofibrate & insoitolnicotinate	2.42	2	0	aromatic ether; ethyl ester; monochlorobenzenes	anticholesteremic drug; antilipemic drug; geroprotector; PPARalpha agonist
clonazepam Clonazepam: An anticonvulsant used for several types of seizures, including myotonic or atonic seizures, photosensitive epilepsy, and absence seizures, although tolerance may develop. It is seldom effective in generalized tonic-clonic or partial seizures. The mechanism of action appears to involve the enhancement of GAMMA-AMINOBUTYRIC ACID receptor responses.. clonazepam : 1,3-Dihydro-2H-1,4-benzodiazepin-2-one in which the hydrogens at positions 5 and 7 are substituted by 2-chlorophenyl and nitro groups, respectively. It is used in the treatment of all types of epilepsy and seizures, as well as myoclonus and associated abnormal movements, and panic disorders. However, its use can be limited by the development of tolerance and by sedation.	1.95	1	0	1,4-benzodiazepinone; monochlorobenzenes	anticonvulsant; anxiolytic drug; GABA modulator
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.	2.68	3	0	clonidine; imidazoline
cloperastine cloperastine: RN given refers to parent cpd	3.15	1	0	diarylmethane
clotrimazole [no description available]	2.04	1	0	conazole antifungal drug; imidazole antifungal drug; imidazoles; monochlorobenzenes	antiinfective agent; environmental contaminant; xenobiotic
4-cresol 4-cresol: RN given refers to parent cpd. p-cresol : A cresol that consists of toluene substituted by a hydroxy group at position 4. It is a metabolite of aromatic amino acid metabolism produced by intestinal microflora in humans and animals.	2.82	3	0	cresol	Escherichia coli metabolite; human metabolite; uremic toxin
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.	3.07	5	0	non-proteinogenic alpha-amino acid	EC 2.5.1.6 (methionine adenosyltransferase) inhibitor
cyclopentylamine [no description available]	3.1	5	0
cystamine [no description available]	2.01	1	0	organic disulfide; primary amino compound	EC 2.3.2.13 (protein-glutamine gamma-glutamyltransferase) inhibitor
dantrolene Dantrolene: Skeletal muscle relaxant that acts by interfering with excitation-contraction coupling in the muscle fiber. It is used in spasticity and other neuromuscular abnormalities. Although the mechanism of action is probably not central, dantrolene is usually grouped with the central muscle relaxants.. dantrolene : The hydrazone resulting from the formal condensation of 5-(4-nitrophenyl)furfural with 1-aminohydantoin. A ryanodine receptor antagonist used for the relief of chronic severe spasticity and malignant hyperthermia.	1.98	1	0	hydrazone; imidazolidine-2,4-dione	muscle relaxant; neuroprotective agent; ryanodine receptor antagonist
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.	2.25	1	0	acyclic desferrioxamine	bacterial metabolite; ferroptosis inhibitor; iron chelator; siderophore
desipramine Desipramine: A tricyclic dibenzazepine compound that potentiates neurotransmission. Desipramine selectively blocks reuptake of norepinephrine from the neural synapse, and also appears to impair serotonin transport. This compound also possesses minor anticholinergic activity, through its affinity to muscarinic receptors.. desipramine : A dibenzoazepine consisting of 10,11-dihydro-5H-dibenzo[b,f]azepine substituted on nitrogen with a 3-(methylamino)propyl group.	2.68	3	0	dibenzoazepine; secondary amino compound	adrenergic uptake inhibitor; alpha-adrenergic antagonist; antidepressant; cholinergic antagonist; drug allergen; EC 3.1.4.12 (sphingomyelin phosphodiesterase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; H1-receptor antagonist; serotonin uptake inhibitor
amphetamine Amphetamine: A powerful central nervous system stimulant and sympathomimetic. Amphetamine has multiple mechanisms of action including blocking uptake of adrenergics and dopamine, stimulation of release of monamines, and inhibiting monoamine oxidase. Amphetamine is also a drug of abuse and a psychotomimetic. The l- and the d,l-forms are included here. The l-form has less central nervous system activity but stronger cardiovascular effects. The d-form is DEXTROAMPHETAMINE.. 1-phenylpropan-2-amine : A primary amine that is isopropylamine in which a hydrogen attached to one of the methyl groups has been replaced by a phenyl group.. amphetamine : A racemate comprising equimolar amounts of (R)-amphetamine (also known as levamphetamine or levoamphetamine) and (S)-amphetamine (also known as dexamfetamine or dextroamphetamine.	2.92	4	0	primary amine
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.	3.48	8	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.	2.65	3	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
dibenzothiophene dibenzothiophene : A mancude organic heterotricyclic parent that consists of a thiophene ring flanked by two benzene rings ortho-fused across the 2,3- and 4,5-positions.	2.21	1	0	dibenzothiophenes; mancude organic heterotricyclic parent	keratolytic drug
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.	2.07	1	0	aromatic ether; monocarboxylic acid amide; tertiary amino compound	topical anaesthetic
dibutyl phthalate Dibutyl Phthalate: A plasticizer used in most plastics and found in water, air, soil, plants and animals. It may have some adverse effects with long-term exposure.. dibutyl phthalate : A phthalate ester that is the diester obtained by the formal condensation of the carboxy groups of phthalic acid with two molecules of butan-1-ol. Although used extensively as a plasticiser, it is a ubiquitous environmental contaminant that poses a risk to humans.	2.01	1	0	diester; phthalate ester	EC 3.2.1.20 (alpha-glucosidase) inhibitor; environmental contaminant; metabolite; plasticiser; teratogenic agent
dicamba Dicamba: A chlorinated organic herbicide.. dicamba : A methoxybenzoic acid that is O-methylsalicylic acid substituted by chloro groups at positions 3 and 6.	2.52	2	0	dichlorobenzene; methoxybenzoic acid	agrochemical; environmental contaminant; herbicide; synthetic auxin; xenobiotic
dichlobanil 2,6-dichlorobenzonitrile : A nitrile that is benzonitrile which is substituted by chlorines at positions 2 and 6. A cellulose synthesis inhibitor, it is used as a pre-emergent and early post-emergent herbicide.	2.11	1	0	dichlorobenzene; nitrile	agrochemical; cellulose synthesis inhibitor; environmental contaminant; herbicide; xenobiotic
diclofenac Diclofenac: A non-steroidal anti-inflammatory agent (NSAID) with antipyretic and analgesic actions. It is primarily available as the sodium salt.. diclofenac : A monocarboxylic acid consisting of phenylacetic acid having a (2,6-dichlorophenyl)amino group at the 2-position.	4.9	1	1	amino acid; aromatic amine; dichlorobenzene; monocarboxylic acid; secondary amino compound	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
diethylcarbamazine Diethylcarbamazine: An anthelmintic used primarily as the citrate in the treatment of filariasis, particularly infestations with Wucheria bancrofti or Loa loa.	2.36	2	0	N-carbamoylpiperazine; N-methylpiperazine
dihydrocytochalasin b dihydrocytochalasin B: inhibits cell motility in many eucaryotic cells	1.99	1	0
dilazep Dilazep: Coronary vasodilator with some antiarrhythmic activity.. dilazep : A member of the class of diazepanes that is 1,4-diazepane substituted by 3-[(3,4,5-trimethoxybenzoyl)oxy]propyl groups at positions 1 and 4. It is a potent adenosine uptake inhibitor that exhibits antiplatelet, antianginal and vasodilator properties.	1.96	1	0	benzoate ester; diazepane; diester; methoxybenzenes	cardioprotective agent; platelet aggregation inhibitor; vasodilator agent
dimetridazole Dimetridazole: A compound used to treat histomoniasis in poultry.. dimetridazole : A C-nitro compound that is 5-nitroimidazole in which the hydrogens at positions 1 and 2 are replaced by methyl groups. An antiprotozoal drug, it has been banned by both the Government of Canada and the European Union as a livestock feed additive owing to suspicions of it being carcinogenic.	2.1	1	0	C-nitro compound; imidazoles	antiparasitic agent; antiprotozoal drug
dipalmitoylphosphatidic acid dipalmitoylphosphatidic acid: RN given refers to parent cpd without isomeric designation. dihexadecanoyl phosphatidic acid : A phosphatidic acid in which the phosphatidyl acyl groups are both palmitoyl (hexadecanoyl).	1.97	1	0	phosphatidic acid
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
diphenyleneiodonium diphenyleneiodonium: structure in first source; NADPH oxidase inhibitor. dibenziodolium : An organic cation that is fluorene in which the methylene group is replaced by a positively charged iodine.	3.43	7	0	organic cation
dipyridamole Dipyridamole: A phosphodiesterase inhibitor that blocks uptake and metabolism of adenosine by erythrocytes and vascular endothelial cells. Dipyridamole also potentiates the antiaggregating action of prostacyclin. (From AMA Drug Evaluations Annual, 1994, p752). dipyridamole : A pyrimidopyrimidine that is 2,2',2'',2'''-(pyrimido[5,4-d]pyrimidine-2,6-diyldinitrilo)tetraethanol substituted by piperidin-1-yl groups at positions 4 and 8 respectively. A vasodilator agent, it inhibits the formation of blood clots.	2.35	2	0	piperidines; pyrimidopyrimidine; tertiary amino compound; tetrol	adenosine phosphodiesterase inhibitor; EC 3.5.4.4 (adenosine deaminase) inhibitor; platelet aggregation inhibitor; vasodilator agent
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.	1.99	1	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
2-amino-7-phosphonoheptanoic acid 2-amino-7-phosphonoheptanoic acid: (D)-isomer active as an antagonist of N-methyl-D-aspartate excitation of central neurons; (L)-isomer inactive; RN given refers to cpd without isomeric designation	1.98	1	0
1-phenyl-2-palmitoylamino-3-morpholino-1-propanol 1-phenyl-2-palmitoylamino-3-morpholino-1-propanol: a sphingolipid analog; inhibits the enzyme activity in infected erythrocytes. N-[1-hydroxy-3-(morpholin-4-yl)-1-phenylpropan-2-yl]hexadecanamide : A fatty amide resulting from the formal condensation of palmitic acid with the primary amino group of 2-amino-3-(morpholin-4-yl)-1-phenylpropan-1-ol.	1.99	1	0	benzyl alcohols; fatty amide; morpholines; secondary alcohol; tertiary amino compound
donepezil Donepezil: An indan and piperidine derivative that acts as a selective and reversible inhibitor of ACETYLCHOLINESTERASE. Donepezil is highly selective for the central nervous system and is used in the management of mild to moderate DEMENTIA in ALZHEIMER DISEASE.. donepezil : A racemate comprising equimolar amounts of (R)- and (S)-donepezil. A centrally acting reversible acetylcholinesterase inhibitor, its main therapeutic use is in the treatment of Alzheimer's disease where it is used to increase cortical acetylcholine.. 2-[(1-benzylpiperidin-4-yl)methyl]-5,6-dimethoxyindan-1-one : A member of the class of indanones that is 5,6-dimethoxyindan-1-one which is substituted at position 2 by an (N-benzylpiperidin-4-yl)methyl group.	2.31	1	0	aromatic ether; indanones; piperidines; racemate	EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; nootropic agent
ebselen ebselen : A benzoselenazole that is 1,2-benzoselenazol-3-one carrying an additional phenyl substituent at position 2. Acts as a mimic of glutathione peroxidase.	2.05	1	0	benzoselenazole	anti-inflammatory drug; antibacterial agent; anticoronaviral agent; antifungal agent; antineoplastic agent; antioxidant; apoptosis inducer; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor; EC 2.5.1.7 (UDP-N-acetylglucosamine 1-carboxyvinyltransferase) inhibitor; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor; EC 3.1.3.25 (inositol-phosphate phosphatase) inhibitor; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; EC 3.5.4.1 (cytosine deaminase) inhibitor; EC 5.1.3.2 (UDP-glucose 4-epimerase) inhibitor; enzyme mimic; ferroptosis inhibitor; genotoxin; hepatoprotective agent; neuroprotective agent; radical scavenger
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.	5.2	2	1	trihydroxyanthraquinone	antineoplastic agent; laxative; plant metabolite; tyrosine kinase inhibitor
endothall endothall: minor descriptor (72-82); online & Index Medicus search DICARBOXYLIC ACIDS (72-82)	2.93	4	0
erythrosine Fluoresceins: A family of spiro(isobenzofuran-1(3H),9'-(9H)xanthen)-3-one derivatives. These are used as dyes, as indicators for various metals, and as fluorescent labels in immunoassays.	3.37	7	0
etafenone etafenone: used in therapy of anigna pectoris; RN given refers to parent cpd; synonym baxacor is HCl; structure	2	1	0	aromatic compound
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.	2.07	1	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.	3.42	7	0	ether; volatile organic compound	inhalation anaesthetic; non-polar solvent; refrigerant
fenfluramine Fenfluramine: A centrally active drug that apparently both blocks serotonin uptake and provokes transport-mediated serotonin release.. fenfluramine : A secondary amino compound that is 1-phenyl-propan-2-amine in which one of the meta-hydrogens is substituted by trifluoromethyl, and one of the hydrogens attached to the nitrogen is substituted by an ethyl group. It binds to the serotonin reuptake pump, causing inhbition of serotonin uptake and release of serotonin. The resulting increased levels of serotonin lead to greater serotonin receptor activation which in turn lead to enhancement of serotoninergic transmission in the centres of feeding behavior located in the hypothalamus. This suppresses the appetite for carbohydrates. Fenfluramine was used as the hydrochloride for treatment of diabetes and obesity. It was withdrawn worldwide after reports of heart valve disease and pulmonary hypertension.	1.96	1	0	(trifluoromethyl)benzenes; secondary amino compound	appetite depressant; serotonergic agonist; serotonin uptake inhibitor
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.	2.03	1	0	anilide; monocarboxylic acid amide; piperidines	adjuvant; anaesthesia adjuvant; anaesthetic; intravenous anaesthetic; mu-opioid receptor agonist; opioid analgesic
fluconazole Fluconazole: Triazole antifungal agent that is used to treat oropharyngeal CANDIDIASIS and cryptococcal MENINGITIS in AIDS.. fluconazole : A member of the class of triazoles that is propan-2-ol substituted at position 1 and 3 by 1H-1,2,4-triazol-1-yl groups and at position 2 by a 2,4-difluorophenyl group. It is an antifungal drug used for the treatment of mucosal candidiasis and for systemic infections including systemic candidiasis, coccidioidomycosis, and cryptococcosis.	4.18	3	1	conazole antifungal drug; difluorobenzene; tertiary alcohol; triazole antifungal drug	environmental contaminant; P450 inhibitor; xenobiotic
flucytosine Flucytosine: A fluorinated cytosine analog that is used as an antifungal agent.. flucytosine : An organofluorine compound that is cytosine that is substituted at position 5 by a fluorine. A prodrug for the antifungal 5-fluorouracil, it is used for the treatment of systemic fungal infections.	2.08	1	0	aminopyrimidine; nucleoside analogue; organofluorine compound; pyrimidine antifungal drug; pyrimidone	prodrug
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.	2.08	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.	2.44	2	0	ethyl ester; imidazobenzodiazepine; organofluorine compound	antidote to benzodiazepine poisoning; GABA antagonist
flunitrazepam Flunitrazepam: A benzodiazepine with pharmacologic actions similar to those of DIAZEPAM that can cause ANTEROGRADE AMNESIA. Some reports indicate that it is used as a date rape drug and suggest that it may precipitate violent behavior. The United States Government has banned the importation of this drug.. flunitrazepam : A 1,4-benzodiazepinone that is nitrazepam substituted by a methyl group at position 1 and by a fluoro group at position 2'. It is a potent hypnotic, sedative, and amnestic drug used to treat chronic insomnia.	2	1	0	1,4-benzodiazepinone; C-nitro compound; monofluorobenzenes	anxiolytic drug; GABAA receptor agonist; sedative
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.	2.7	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.	2.02	1	0	(trifluoromethyl)benzenes; aromatic ether; secondary amino compound
furosemide Furosemide: A benzoic-sulfonamide-furan. It is a diuretic with fast onset and short duration that is used for EDEMA and chronic RENAL INSUFFICIENCY.. furosemide : A chlorobenzoic acid that is 4-chlorobenzoic acid substituted by a (furan-2-ylmethyl)amino and a sulfamoyl group at position 2 and 5 respectively. It is a diuretic used in the treatment of congestive heart failure.	3.76	2	1	chlorobenzoic acid; furans; sulfonamide	environmental contaminant; loop diuretic; xenobiotic
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.	4.75	5	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.	1.98	1	0	benzoate ester
gaboxadol gaboxadol: GABA agonist; inhibitor of GABA uptake systems; structure	3.08	1	0	oxazole
gemfibrozil [no description available]	2.21	1	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.	1.95	1	0
2,5-dihydroxybenzoic acid 2,5-dihydroxybenzoic acid: RN given refers to parent cpd; a oxidative product of saligenin. 2,5-dihydroxybenzoic acid : A dihydroxybenzoic acid having the two hydroxy groups at the 2- and 5-positions.	2.52	2	0	dihydroxybenzoic acid	EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; fungal metabolite; human metabolite; MALDI matrix material; mouse metabolite
gliclazide Gliclazide: An oral sulfonylurea hypoglycemic agent which stimulates insulin secretion.	2	1	0	N-sulfonylurea	hypoglycemic agent; insulin secretagogue; radical scavenger
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.	2.92	4	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.	3.59	9	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
gossypol Gossypol: A dimeric sesquiterpene found in cottonseed (GOSSYPIUM). The (-) isomer is active as a male contraceptive (CONTRACEPTIVE AGENTS, MALE) whereas toxic symptoms are associated with the (+) isomer.	3.12	5	0
guaifenesin Guaifenesin: An expectorant that also has some muscle relaxing action. It is used in many cough preparations.	2.46	2	0	methoxybenzenes
guanethidine Guanethidine: An antihypertensive agent that acts by inhibiting selectively transmission in post-ganglionic adrenergic nerves. It is believed to act mainly by preventing the release of norepinephrine at nerve endings and causes depletion of norepinephrine in peripheral sympathetic nerve terminals as well as in tissues.. guanethidine : A member of the class of guanidines in which one of the hydrogens of the amino group has been replaced by a 2-azocan-1-ylethyl group.. guanethidine sulfate : A organic sulfate salt composed of two molecules of guanethidine and one of sulfuric acid.	1.98	1	0	azocanes; guanidines	adrenergic antagonist; antihypertensive agent; sympatholytic agent
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.	2.76	3	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.	3.94	13	0	aromatic ketone; hydroxypiperidine; monochlorobenzenes; organofluorine compound; tertiary alcohol	antidyskinesia agent; antiemetic; dopaminergic antagonist; first generation antipsychotic; serotonergic antagonist
halothane [no description available]	2.34	2	0	haloalkane; organobromine compound; organochlorine compound; organofluorine compound	inhalation anaesthetic
miltefosine miltefosine: hexadecyl phosphocholine derivative of cisplatin; did not substantially activate HIV long terminal repeat; less toxic than cisplatin. miltefosine : A phospholipid that is the hexadecyl monoester of phosphocholine.	7.58	2	0	phosphocholines; phospholipid	anti-inflammatory agent; anticoronaviral agent; antifungal agent; antineoplastic agent; antiprotozoal drug; apoptosis inducer; immunomodulator; protein kinase inhibitor
hexobarbital Hexobarbital: A barbiturate that is effective as a hypnotic and sedative.. hexobarbital : A member of the class of barbiturates taht is barbituric acid substituted at N-1 by methyl and at C-5 by methyl and cyclohex-1-enyl groups.	2.93	4	0	barbiturates
beta-thujaplicin beta-thujaplicin: structure. beta-thujaplicin : A monoterpenoid that is cyclohepta-2,4,6-trien-1-one substituted by a hydroxy group at position 2 and an isopropyl group at position 4. Isolated from Thuja plicata and Chamaecyparis obtusa, it exhibits antimicrobial activities.	2.7	3	0	cyclic ketone; enol; monoterpenoid	antibacterial agent; antifungal agent; antineoplastic agent; antiplasmodial drug; plant metabolite
hydroxyzine Hydroxyzine: A histamine H1 receptor antagonist that is effective in the treatment of chronic urticaria, dermatitis, and histamine-mediated pruritus. Unlike its major metabolite CETIRIZINE, it does cause drowsiness. It is also effective as an antiemetic, for relief of anxiety and tension, and as a sedative.. hydroxyzine : A N-alkylpiperazine that is piperzine in which the nitrogens atoms are substituted by 2-(2-hydroxyethoxy)ethyl and (4-chlorophenyl)(phenyl)methyl groups respectively.	1.95	1	0	hydroxyether; monochlorobenzenes; N-alkylpiperazine	anticoronaviral agent; antipruritic drug; anxiolytic drug; dermatologic drug; H1-receptor antagonist
hypericin [no description available]	2.71	3	0
ibuprofen Midol: combination of cinnamedrine, phenacetin, aspirin & caffeine	3.16	5	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.	3.08	5	0	benzenes; monocarboxylic acid amide; tertiary amino compound	anti-arrhythmia drug; drug allergen; environmental contaminant; local anaesthetic; xenobiotic
mephentermine Mephentermine: A sympathomimetic agent with specificity for alpha-1 adrenergic receptors. It is used to maintain BLOOD PRESSURE in hypotensive states such as following SPINAL ANESTHESIA.	2.35	2	0	amphetamines
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.	3.49	8	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.	3.06	5	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]	1.95	1	0
indolepropionic acid indolepropionic acid: structure in third source. 3-(1H-indol-3-yl)propanoic acid : An indol-3-yl carboxylic acid that is propionic acid substituted by a 1H-indol-3-yl group at position 3.	2.1	1	0	indol-3-yl carboxylic acid	auxin; human metabolite; plant metabolite
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.	2.39	2	0	3-isobutyl-1-methylxanthine
isoflurane Isoflurane: A stable, non-explosive inhalation anesthetic, relatively free from significant side effects.	1.99	1	0	organofluorine compound	inhalation anaesthetic
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).	1.93	1	0	carbohydrazide	antitubercular agent; drug allergen
2-propanol 2-Propanol: An isomer of 1-PROPANOL. It is a colorless liquid having disinfectant properties. It is used in the manufacture of acetone and its derivatives and as a solvent. Topically, it is used as an antiseptic.. propan-2-ol : A secondary alcohol that is propane in which one of the hydrogens attached to the central carbon is substituted by a hydroxy group.	6.14	10	1	secondary alcohol; secondary fatty alcohol	protic solvent
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.	5.31	13	1	catechols; secondary alcohol; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; cardiotonic drug; sympathomimetic agent
staurosporine aglycone staurosporine aglycone: metabolite from culture broth of Nocardiopsis sp.; a neurotrophin antag; inhibits BDNF TrkB receptor	2.71	3	0
ketamine Ketamine: A cyclohexanone derivative used for induction of anesthesia. Its mechanism of action is not well understood, but ketamine can block NMDA receptors (RECEPTORS, N-METHYL-D-ASPARTATE) and may interact with sigma receptors.. ketamine : A member of the class of cyclohexanones in which one of the hydrogens at position 2 is substituted by a 2-chlorophenyl group, while the other is substituted by a methylamino group.	2.7	3	0	cyclohexanones; monochlorobenzenes; secondary amino compound	analgesic; environmental contaminant; intravenous anaesthetic; neurotoxin; NMDA receptor antagonist; xenobiotic
ketoprofen Ketoprofen: An IBUPROFEN-type anti-inflammatory analgesic and antipyretic. It is used in the treatment of rheumatoid arthritis and osteoarthritis.. ketoprofen : An oxo monocarboxylic acid that consists of propionic acid substituted by a 3-benzoylphenyl group at position 2.	4.9	1	1	benzophenones; oxo monocarboxylic acid	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-steroidal anti-inflammatory drug; xenobiotic
kinetin Kinetin: A furanyl adenine found in PLANTS and FUNGI. It has plant growth regulation effects.. cytokinin : A phytohormone that promote cell division, or cytokinesis, in plant roots and shoots.. kinetin : A member of the class of 6-aminopurines that is adenine carrying a (furan-2-ylmethyl) substituent at the exocyclic amino group.	3.98	13	0	6-aminopurines; furans	cytokinin; geroprotector
kojic acid [no description available]	2.02	1	0	4-pyranones; enol; primary alcohol	Aspergillus metabolite; EC 1.10.3.1 (catechol oxidase) inhibitor; EC 1.10.3.2 (laccase) inhibitor; EC 1.13.11.24 (quercetin 2,3-dioxygenase) inhibitor; EC 1.14.18.1 (tyrosinase) inhibitor; EC 1.4.3.3 (D-amino-acid oxidase) inhibitor; NF-kappaB inhibitor; skin lightening agent
2-amino-3-phosphonopropionic acid 2-amino-3-phosphonopropionic acid: metabotropic glutamate receptor antagonist; do not confuse AP-3 used as an abbreviation for this with enhancer-binding protein AP-3 (a trans-activator) or clathrin assembly protein AP-3. 2-amino-3-phosphonopropanoic acid : A non-proteinogenc alpha-amino acid that is alanine in which one of the hydrogens of the terminal methyl group has been replaced by a dihydroxy(oxido)-lambda(5)-phosphanyl group.	2.38	2	0	alanine derivative; non-proteinogenic alpha-amino acid; phosphonic acids	human metabolite; metabotropic glutamate receptor antagonist
mimosine Mimosine: 3-Hydroxy-4-oxo-1(4H)-pyridinealanine. An antineoplastic alanine-substituted pyridine derivative isolated from Leucena glauca.	2.21	1	0	alpha-amino acid
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.	2.96	4	0	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; antibacterial agent; plant metabolite
tetramisole 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole : An imidazothiazole that is imidazo[2,1-b][1,3]thiazole in which the double bonds at the 2-3 and 5-6 positions have been reduced to single bonds and in which one of the hydrogens at position 6 is replaced by a phenyl group.. tetramisole : A racemate comprising equimolar amounts of levamisole and dexamisole.	1.95	1	0	imidazothiazole	environmental contaminant; xenobiotic
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.	2.01	1	0	monocarboxylic acid amide; monochlorobenzenes; piperidines; tertiary alcohol	anticoronaviral agent; antidiarrhoeal drug; mu-opioid receptor agonist
losartan Losartan: An antagonist of ANGIOTENSIN TYPE 1 RECEPTOR with antihypertensive activity due to the reduced pressor effect of ANGIOTENSIN II.. losartan : A biphenylyltetrazole where a 1,1'-biphenyl group is attached at the 5-position and has an additional trisubstituted imidazol-1-ylmethyl group at the 4'-position	4.9	1	1	biphenylyltetrazole; imidazoles	angiotensin receptor antagonist; anti-arrhythmia drug; antihypertensive agent; endothelin receptor antagonist
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.	2.05	1	0	cyclopentanones; monocarboxylic acid	antipyretic; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; prodrug
6-anilino-5,8-quinolinedione 6-anilino-5,8-quinolinedione: structure given in first source; SRS-A & guanylate cyclase antagonist. 6-anilino-5,8-quinolinedione : A quinolone that is quinoline-5,8-dione in which the hydrogen at position 6 is replaced by an anilino group.	2.1	1	0	aminoquinoline; aromatic amine; p-quinones; quinolone	antineoplastic agent; EC 4.6.1.2 (guanylate cyclase) inhibitor
malathion Malathion: A wide spectrum aliphatic organophosphate insecticide widely used for both domestic and commercial agricultural purposes.. malathion : A racemate comprising equimolar amounts of (R) and (S)-malathion. It is a broad spectrum organophosphate proinsecticide used to control a wide range of pests including Coleoptera, Diptera, fruit flies, mosquitos and spider mites.. diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate : A diester that is diethyl succinate in which position 2 is substituted by a (dimethoxyphosphorothioyl)thio group.	1.94	1	0	diester; ethyl ester; organic thiophosphate
edaravone [no description available]	4.9	1	1	pyrazolone	antioxidant; radical scavenger
mecamylamine Mecamylamine: A nicotinic antagonist that is well absorbed from the gastrointestinal tract and crosses the blood-brain barrier. Mecamylamine has been used as a ganglionic blocker in treating hypertension, but, like most ganglionic blockers, is more often used now as a research tool.	2.06	1	0	primary aliphatic amine
mechlorethamine nitrogen mustard : Compounds having two beta-haloalkyl groups bound to a nitrogen atom, as in (X-CH2-CH2)2NR.	2.35	2	0	nitrogen mustard; organochlorine compound	alkylating agent
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.	2.21	1	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
memantine [no description available]	5.12	14	0	adamantanes; primary aliphatic amine	antidepressant; antiparkinson drug; dopaminergic agent; neuroprotective agent; NMDA receptor antagonist
vitamin k 3 Vitamin K 3: A synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo.	2.43	2	0	1,4-naphthoquinones; vitamin K	angiogenesis inhibitor; antineoplastic agent; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; human urinary metabolite; nutraceutical
meperidine Meperidine: A narcotic analgesic that can be used for the relief of most types of moderate to severe pain, including postoperative pain and the pain of labor. Prolonged use may lead to dependence of the morphine type; withdrawal symptoms appear more rapidly than with morphine and are of shorter duration.. pethidine : A piperidinecarboxylate ester that is piperidine which is substituted by a methyl group at position 1 and by phenyl and ethoxycarbonyl groups at position 4. It is an analgesic which is used for the treatment of moderate to severe pain, including postoperative pain and labour pain.	2.35	2	0	ethyl ester; piperidinecarboxylate ester; tertiary amino compound	antispasmodic drug; kappa-opioid receptor agonist; mu-opioid receptor agonist; opioid analgesic
mephenesin Mephenesin: A centrally acting muscle relaxant with a short duration of action.. 1-(2-methylphenyl)glycerol : A glycerol ether in which a single 2-methylphenyl group is attached at position 1 of glycerol via an ether linkage.	2.34	2	0	aromatic ether; glycerol ether
mephenytoin Mephenytoin: An anticonvulsant effective in tonic-clonic epilepsy (EPILEPSY, TONIC-CLONIC). It may cause blood dyscrasias.. mephenytoin : An imidazolidine-2,4-dione (hydantoin) in which the imidazolidine nucleus carries a methyl group at N-3 and has ethyl and phenyl substituents at C-5. An anticonvulsant, it is no longer available in the USA or the UK but is still studied largely because of its interesting hydroxylation polymorphism.	4.9	1	1	imidazolidine-2,4-dione	anticonvulsant
mescaline Mescaline: Hallucinogenic alkaloid isolated from the flowering heads (peyote) of Lophophora (formerly Anhalonium) williamsii, a Mexican cactus used in Indian religious rites and as an experimental psychotomimetic. Among its cellular effects are agonist actions at some types of serotonin receptors. It has no accepted therapeutic uses although it is legal for religious use by members of the Native American Church.. mescaline : A phenethylamine alkaloid that is phenethylamine substituted at positions 3, 4 and 5 by methoxy groups.	2.35	2	0	methoxybenzenes; phenethylamine alkaloid; primary amino compound	hallucinogen
metaproterenol Metaproterenol: A beta-2 adrenergic agonist used in the treatment of ASTHMA and BRONCHIAL SPASM.. orciprenaline : A racemate composed of equimolar amounts of (R)- and (S)-orciprenaline. Used (as its sulfate salt) to relax the airway muscles and improve breathing for patients suffering from asthma or bronchitis.. 5-[1-hydroxy-2-(isopropanylamino)ethyl]benzene-1,3-diol : A member of the class of resorcinols bearing an additional 1-hydroxy-2-(isopropanylamino)ethyl substituent at position 5 of resorcinol itself.	1.94	1	0	aralkylamino compound; phenylethanolamines; resorcinols; secondary alcohol; secondary amino compound
metformin Metformin: A biguanide hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. Metformin improves glycemic control by improving insulin sensitivity and decreasing intestinal absorption of glucose. (From Martindale, The Extra Pharmacopoeia, 30th ed, p289). metformin : A member of the class of guanidines that is biguanide the carrying two methyl substituents at position 1.	2.59	2	0	guanidines	environmental contaminant; geroprotector; hypoglycemic agent; xenobiotic
methacrylic acid methacrylic acid: RN given refers to parent cpd. methacrylic acid : An alpha,beta-unsaturated monocarboxylic acid that is acrylic acid in which the hydrogen at position 2 is substituted by a methyl group.	2.06	1	0	alpha,beta-unsaturated monocarboxylic acid
methapyrilene Methapyrilene: Histamine H1 antagonist with sedative action used as a hypnotic and in allergies.. methapyrilene : A member of the class of ethylenediamine derivatives that is ethylenediamine in which one of the nitrogens is substituted by two methyl groups, and the other nitrogen is substituted by a 2-pyridyl group and a (2-thienyl)methyl group.	1.95	1	0	ethylenediamine derivative	anti-allergic agent; carcinogenic agent; H1-receptor antagonist; sedative
methoxsalen Methoxsalen: A naturally occurring furocoumarin compound found in several species of plants, including Psoralea corylifolia. It is a photoactive substance that forms DNA ADDUCTS in the presence of ultraviolet A irradiation.. methoxsalen : A member of the class of psoralens that is 7H-furo[3,2-g]chromen-7-one in which the 9 position is substituted by a methoxy group. It is a constituent of the fruits of Ammi majus. Like other psoralens, trioxsalen causes photosensitization of the skin. It is administered topically or orally in conjunction with UV-A for phototherapy treatment of vitiligo and severe psoriasis.	2.17	1	0	aromatic ether; psoralens	antineoplastic agent; cross-linking reagent; dermatologic drug; photosensitizing agent; plant metabolite
nocodazole [no description available]	6.32	50	0	aromatic ketone; benzimidazoles; carbamate ester; thiophenes	antimitotic; antineoplastic agent; microtubule-destabilising agent; tubulin modulator
methyl salicylate methyl salicylate: used in over-the-counter liniments, ointments, lotions for relief of musculoskeletal aches and pains; has hemolytic effect on human & sheep erythrocytes; RN given refers to parent cpd; structure in Merck Index, 9th ed, #5990. methyl salicylate : A benzoate ester that is the methyl ester of salicylic acid.	6.69	40	0	benzoate ester; methyl ester; salicylates	flavouring agent; insect attractant; metabolite
methyl methanesulfonate [no description available]	1.99	1	0	methanesulfonate ester	alkylating agent; apoptosis inducer; carcinogenic agent; genotoxin; mutagen
methylphenidate Methylphenidate: A central nervous system stimulant used most commonly in the treatment of ATTENTION DEFICIT DISORDER in children and for NARCOLEPSY. Its mechanisms appear to be similar to those of DEXTROAMPHETAMINE. The d-isomer of this drug is referred to as DEXMETHYLPHENIDATE HYDROCHLORIDE.. methylphenidate : A racemate comprising equimolar amounts of the two threo isomers of methyl phenyl(piperidin-2-yl)acetate. A central stimulant and indirect-acting sympathomimetic, is used (generally as the hydrochloride salt) in the treatment of hyperactivity disorders in children and for the treatment of narcolepsy.. methyl phenyl(piperidin-2-yl)acetate : A amino acid ester that is methyl phenylacetate in which one of the hydrogens alpha to the carbonyl group is replaced by a piperidin-2-yl group.	1.94	1	0	beta-amino acid ester; methyl ester; piperidines
metoclopramide Metoclopramide: A dopamine D2 antagonist that is used as an antiemetic.. metoclopramide : A member of the class of benzamides resulting from the formal condensation of 4-amino-5-chloro-2-methoxybenzoic acid with the primary amino group of N,N-diethylethane-1,2-diamine.	1.96	1	0	benzamides; monochlorobenzenes; substituted aniline; tertiary amino compound	antiemetic; dopaminergic antagonist; environmental contaminant; gastrointestinal drug; xenobiotic
metoprolol Metoprolol: A selective adrenergic beta-1 blocking agent that is commonly used to treat ANGINA PECTORIS; HYPERTENSION; and CARDIAC ARRHYTHMIAS.. metoprolol : A propanolamine that is 1-(propan-2-ylamino)propan-2-ol substituted by a 4-(2-methoxyethyl)phenoxy group at position 1.	3.34	1	1	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.	2.38	2	0	C-nitro compound; imidazoles; primary alcohol	antiamoebic agent; antibacterial drug; antimicrobial agent; antiparasitic agent; antitrichomonal drug; environmental contaminant; prodrug; radiosensitizing agent; xenobiotic
mexiletine Mexiletine: Antiarrhythmic agent pharmacologically similar to LIDOCAINE. It may have some anticonvulsant properties.. mexiletine : An aromatic ether which is 2,6-dimethylphenyl ether of 2-aminopropan-1-ol.	2.02	1	0	aromatic ether; primary amino compound	anti-arrhythmia drug
miconazole Miconazole: An imidazole antifungal agent that is used topically and by intravenous infusion.. 1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole : A member of the class of imidazoles that is 1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanol in which the hydroxyl hydrogen is replaced by a 2,4-dichlorobenzyl group.. miconazole : A racemate composed of equimolar amounts of (R)- and (S)-miconazole. Used (as its nitrate salt) to treat skin infections such as athlete's foot, jock itch, ringworm and other fungal skin infections. It inhibits the synthesis of ergosterol, a critical component of fungal cell membranes.	2.45	2	0	dichlorobenzene; ether; imidazoles
midazolam Midazolam: A short-acting hypnotic-sedative drug with anxiolytic and amnestic properties. It is used in dentistry, cardiac surgery, endoscopic procedures, as preanesthetic medication, and as an adjunct to local anesthesia. The short duration and cardiorespiratory stability makes it useful in poor-risk, elderly, and cardiac patients. It is water-soluble at pH less than 4 and lipid-soluble at physiological pH.. midazolam : An imidazobenzodiazepine that is 4H-imidazo[1,5-a][1,4]benzodiazepine which is substituted by a methyl, 2-fluorophenyl and chloro groups at positions 1, 6 and 8, respectively.	2.54	2	0	imidazobenzodiazepine; monofluorobenzenes; organochlorine compound	anticonvulsant; antineoplastic agent; anxiolytic drug; apoptosis inducer; central nervous system depressant; GABAA receptor agonist; general anaesthetic; muscle relaxant; sedative
monodansylcadaverine monodansylcadaverine: inhibits cross linkage of fibrin. monodansylcadaverine : A sulfonamide obtained by formal condensation of the sulfo group of 5-(dimethylamino)naphthalene-1-sulfonic acid with one of the amino groups of cadaverine.	1.98	1	0	aminonaphthalene; primary amino compound; sulfonamide; tertiary amino compound	EC 2.3.2.13 (protein-glutamine gamma-glutamyltransferase) inhibitor; fluorochrome; protective agent
moxisylyte Moxisylyte: An alpha-adrenergic blocking agent that is used in Raynaud's disease. It is also used locally in the eye to reverse the mydriasis caused by phenylephrine and other sympathomimetic agents. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1312)	3.04	1	0	monoterpenoid
muscimol Muscimol: A neurotoxic isoxazole isolated from species of AMANITA. It is obtained by decarboxylation of IBOTENIC ACID. Muscimol is a potent agonist of GABA-A RECEPTORS and is used mainly as an experimental tool in animal and tissue studies.. muscimol : A member of the class of isoxazoles that is 1,2-oxazol-3(2H)-one substituted by an aminomethyl group at position 5. It has been isolated from mushrooms of the genus Amanita.	2.43	2	0	alkaloid; isoxazoles; primary amino compound	fungal metabolite; GABA agonist; oneirogen; psychotropic drug
deet N,N-diethyl-m-toluamide : A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of m-toluic acid with the nitrogen of diethylamine. First developed by the U.S. Army in 1946 for use by military personnel in insect-infested areas, it is the most widely used insect repellent worldwide.	3.44	7	0	benzamides; monocarboxylic acid amide	environmental contaminant; insect repellent; xenobiotic
n-(6-aminohexyl)-1-naphthalenesulfonamide N-(6-aminohexyl)-1-naphthalenesulfonamide: calmodulin antagonist; RN given refers to parent cpd	2.13	1	0	naphthalenes; sulfonic acid derivative
ethylmaleimide Ethylmaleimide: A sulfhydryl reagent that is widely used in experimental biochemical studies.	3.37	7	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
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.	2.07	1	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.	3.15	5	0	C-nitro compound; dihydropyridine; methyl ester	calcium channel blocker; human metabolite; tocolytic agent; vasodilator agent
niflumic acid Niflumic Acid: An analgesic and anti-inflammatory agent used in the treatment of rheumatoid arthritis.	2.48	2	0	aromatic carboxylic acid; pyridines
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
nitrazepam Nitrazepam: A benzodiazepine derivative used as an anticonvulsant and hypnotic.. nitrazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one which is substituted at positions 5 and 7 by phenyl and nitro groups, respectively. It is used as a hypnotic for the short-term management of insomnia and for the treatment of epileptic spasms in infants (West's syndrome).	1.95	1	0	1,4-benzodiazepinone; C-nitro compound	anticonvulsant; antispasmodic drug; drug metabolite; GABA modulator; sedative
nomifensine Nomifensine: An isoquinoline derivative that prevents dopamine reuptake into synaptosomes. The maleate was formerly used in the treatment of depression. It was withdrawn worldwide in 1986 due to the risk of acute hemolytic anemia with intravascular hemolysis resulting from its use. In some cases, renal failure also developed. (From Martindale, The Extra Pharmacopoeia, 30th ed, p266). nomifensine : An N-methylated tetrahydroisoquinoline carrying phenyl and amino substituents at positions C-4 and C-8, respectively.	1.98	1	0	isoquinolines	dopamine uptake inhibitor
5-nitro-2-(3-phenylpropylamino)benzoic acid 5-nitro-2-(3-phenylpropylamino)benzoic acid: structure given in first source; chloride channel antagonist	3	4	0	nitrobenzoic acid
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.	4.9	1	1	aromatic ether; benzimidazoles; pyridines; sulfoxide
oxidopamine Oxidopamine: A neurotransmitter analogue that depletes noradrenergic stores in nerve endings and induces a reduction of dopamine levels in the brain. Its mechanism of action is related to the production of cytolytic free-radicals.. oxidopamine : A benzenetriol that is phenethylamine in which the hydrogens at positions 2, 4, and 5 on the phenyl ring are replaced by hydroxy groups. It occurs naturally in human urine, but is also produced as a metabolite of the drug DOPA (used for the treatment of Parkinson's disease).	2.44	2	0	benzenetriol; catecholamine; primary amino compound	drug metabolite; human metabolite; neurotoxin
oxotremorine m oxotremorine M: structure given in first source	2.05	1	0	quaternary ammonium ion	muscarinic agonist
oxotremorine Oxotremorine: A non-hydrolyzed muscarinic agonist used as a research tool.	2.05	1	0	N-alkylpyrrolidine
oxprenolol Oxprenolol: A beta-adrenergic antagonist used in the treatment of hypertension, angina pectoris, arrhythmias, and anxiety.	4.58	3	2	aromatic ether
oxybutynin oxybutynin: RN given refers to parent cpd. oxybutynin : A racemate comprising equimolar amounts of (R)-oxybutynin and esoxybutynin. An antispasmodic used for the treatment of overactive bladder.	2	1	0	acetylenic compound; carboxylic ester; racemate; tertiary alcohol; tertiary amino compound	antispasmodic drug; calcium channel blocker; local anaesthetic; muscarinic antagonist; muscle relaxant; parasympatholytic
aminosalicylic acid Aminosalicylic Acid: An antitubercular agent often administered in association with ISONIAZID. The sodium salt of the drug is better tolerated than the free acid.. 4-aminosalicylic acid : An aminobenzoic acid that is salicylic acid substituted by an amino group at position 4.	1.93	1	0	aminobenzoic acid; phenols	antitubercular agent
quinone benzoquinone : The simplest members of the class of benzoquinones, consisting of cyclohexadiene which is substituted by two oxo groups.. 1,4-benzoquinone : The simplest member of the class of 1,4-benzoquinones, obtained by the formal oxidation of hydroquinone to the corresponding diketone. It is a metabolite of benzene.. quinone : Compounds having a fully conjugated cyclic dione structure, such as that of benzoquinones, derived from aromatic compounds by conversion of an even number of -CH= groups into -C(=O)- groups with any necessary rearrangement of double bonds (polycyclic and heterocyclic analogues are included).	3.61	2	0	1,4-benzoquinones	cofactor; human xenobiotic metabolite; mouse metabolite
fenclonine Fenclonine: A selective and irreversible inhibitor of tryptophan hydroxylase, a rate-limiting enzyme in the biosynthesis of serotonin (5-HYDROXYTRYPTAMINE). Fenclonine acts pharmacologically to deplete endogenous levels of serotonin.	2.38	2	0	phenylalanine derivative
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.	2.86	4	0	benzylisoquinoline alkaloid; dimethoxybenzene; isoquinolines	antispasmodic drug; vasodilator agent
4-dichlorobenzene dichlorobenzene : Any member of the class of chlorobenzenes carrying two chloro groups at unspecified positions.. 1,4-dichlorobenzene : A dichlorobenzene carrying chloro groups at positions 1 and 4.	2.04	1	0	dichlorobenzene	insecticide
pargyline Pargyline: A monoamine oxidase inhibitor with antihypertensive properties.	2.78	3	0	aromatic amine
pd 98059 2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one: inhibits MAP kinase kinase (MEK) activity, p42 MAPK and p44 MAPK; structure in first source. 2-(2-amino-3-methoxyphenyl)chromen-4-one : A member of the class of monomethoxyflavones that is 3'-methoxyflavone bearing an additional amino substituent at position 2'.	3.57	8	0	aromatic amine; monomethoxyflavone	EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector
pentobarbital Pentobarbital: A short-acting barbiturate that is effective as a sedative and hypnotic (but not as an anti-anxiety) agent and is usually given orally. It is prescribed more frequently for sleep induction than for sedation but, like similar agents, may lose its effectiveness by the second week of continued administration. (From AMA Drug Evaluations Annual, 1994, p236). pentobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and sec-pentyl groups.	2.44	2	0	barbiturates	GABAA receptor agonist
perhexiline Perhexiline: 2-(2,2-Dicyclohexylethyl)piperidine. Coronary vasodilator used especially for angina of effort. It may cause neuropathy and hepatitis.	1.99	1	0	piperidines	cardiovascular drug
phenazopyridine Phenazopyridine: A local anesthetic that has been used in urinary tract disorders. Its use is limited by problems with toxicity (primarily blood disorders) and potential carcinogenicity.. phenazopyridine : A diaminopyridine that is 2,6-diaminopyridine substituted at position 3 by a phenylazo group. A local anesthetic that has topical analgesic effect on mucosa lining of the urinary tract. Its use is limited by problems with toxicity (primarily blood disorders) and potential carcinogenicity.	2.31	1	0	diaminopyridine; monoazo compound	anticoronaviral agent; carcinogenic agent; local anaesthetic; non-narcotic analgesic
phenmetrazine Phenmetrazine: A sympathomimetic drug used primarily as an appetite depressant. Its actions and mechanisms are similar to DEXTROAMPHETAMINE.. phenmetrazine : A member of the class of morpholines that is morpholine substituted with a phenyl group at position 2 and a methyl group at position 3.	1.94	1	0	morpholines	metabolite; sympathomimetic agent
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.	5.73	6	1	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.	2.21	1	0	2,1-benzoxathiole; arenesulfonate ester; phenols; sultone	acid-base indicator; diagnostic agent; two-colour indicator
phenoxybenzamine Phenoxybenzamine: An alpha-adrenergic antagonist with long duration of action. It has been used to treat hypertension and as a peripheral vasodilator.	1.96	1	0	aromatic amine
oxophenylarsine oxophenylarsine: inhibits protein-tyrosine-phosphatase. phenylarsine oxide : An arsine oxide derived from phenylarsine.	2.06	1	0	arsine oxides	antineoplastic agent; apoptosis inducer; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor
phloretin [no description available]	3.2	6	0	dihydrochalcones	antineoplastic agent; plant metabolite
pinacidil Pinacidil: A guanidine that opens POTASSIUM CHANNELS producing direct peripheral vasodilatation of the ARTERIOLES. It reduces BLOOD PRESSURE and peripheral resistance and produces fluid retention. (Martindale The Extra Pharmacopoeia, 31st ed)	3.26	6	0	pyridines
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.	3.33	1	1	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.	3.4	1	1	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
piracetam Piracetam: A compound suggested to be both a nootropic and a neuroprotective agent.	2.06	1	0	organonitrogen compound; organooxygen compound
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.	3.4	7	0	inorganic chloride; inorganic potassium salt; potassium salt	fertilizer
4-hydroxy-3-methoxybenzene-1-sulfonic acid guaiacolsulfonic acid: elastomer used as dental impression material; mixture of the potassium salt of 4- & 5-guaiacolsulfonic acid; RN given refers to parent cpd. 4-hydroxy-3-methoxybenzene-1-sulfonic acid : An arenesulfonic acid that is guaiacol sulfated at position 4. Commonly used (in the form of its potassium salt) as an expectorant.	2.06	1	0	arenesulfonic acid; guaiacols	expectorant
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.	2.36	2	0	acetamides; ethanolamines; propanolamine; secondary alcohol; secondary amino compound	anti-arrhythmia drug; beta-adrenergic antagonist
primaquine Primaquine: An aminoquinoline that is given by mouth to produce a radical cure and prevent relapse of vivax and ovale malarias following treatment with a blood schizontocide. It has also been used to prevent transmission of falciparum malaria by those returning to areas where there is a potential for re-introduction of malaria. Adverse effects include anemias and GI disturbances. (From Martindale, The Extra Pharmacopeia, 30th ed, p404). primaquine : An N-substituted diamine that is pentane-1,4-diamine substituted by a 6-methoxyquinolin-8-yl group at the N(4) position. It is a drug used in the treatment of malaria and Pneumocystis pneumonia.	1.98	1	0	aminoquinoline; aromatic ether; N-substituted diamine	antimalarial
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.	2.46	2	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.	1.95	1	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.	2.37	2	0	benzoate ester; substituted aniline; tertiary amino compound	central nervous system depressant; drug allergen; local anaesthetic; peripheral nervous system drug
prochlorperazine Prochlorperazine: A phenothiazine antipsychotic used principally in the treatment of NAUSEA; VOMITING; and VERTIGO. It is more likely than CHLORPROMAZINE to cause EXTRAPYRAMIDAL DISORDERS. (From Martindale, The Extra Pharmacopoeia, 30th ed, p612). prochlorperazine : A member of the class of phenothiazines that is 10H-phenothiazine having a chloro substituent at the 2-position and a 3-(4-methylpiperazin-1-yl)propyl group at the N-10 position.	1.95	1	0	N-alkylpiperazine; N-methylpiperazine; organochlorine compound; phenothiazines	alpha-adrenergic antagonist; antiemetic; cholinergic antagonist; dopamine receptor D2 antagonist; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; first generation antipsychotic
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.	2.75	3	0	pyrrolidines; tertiary alcohol	antidyskinesia agent; antiparkinson drug; muscarinic antagonist
promethazine Promethazine: A phenothiazine derivative with histamine H1-blocking, antimuscarinic, and sedative properties. It is used as an antiallergic, in pruritus, for motion sickness and sedation, and also in animals.. promethazine : A tertiary amine that is a substituted phenothiazine in which the ring nitrogen at position 10 is attached to C-3 of an N,N-dimethylpropan-2-amine moiety.	1.92	1	0	phenothiazines; tertiary amine	anti-allergic agent; anticoronaviral agent; antiemetic; antipruritic drug; H1-receptor antagonist; local anaesthetic; sedative
propafenone Propafenone: An antiarrhythmia agent that is particularly effective in ventricular arrhythmias. It also has weak beta-blocking activity.. propafenone : An aromatic ketone that is 3-(propylamino)propane-1,2-diol in which the hydrogen of the primary hydroxy group is replaced by a 2-(3-phenylpropanoyl)phenyl group. It is a class 1C antiarrhythmic drug with local anesthetic effects, and is used as the hydrochloride salt in the management of supraventricular and ventricular arrhythmias.	2	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.	3.04	1	0	xanthenes
propiverine propiverine: anticholinergic used for overactive bladder syndrome	2	1	0	diarylmethane
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.	6.13	9	4	naphthalenes; propanolamine; secondary amine	anti-arrhythmia drug; antihypertensive agent; anxiolytic drug; beta-adrenergic antagonist; environmental contaminant; human blood serum metabolite; vasodilator agent; xenobiotic
propyl gallate Propyl Gallate: Antioxidant for foods, fats, oils, ethers, emulsions, waxes, and transformer oils.	2.07	1	0	trihydroxybenzoic acid
((2-n-butyl-6,7-dichloro-2-cyclopentyl-2,3-dihydro-1-oxo-1h-inden-5-yl)oxy)acetic acid ((2-n-butyl-6,7-dichloro-2-cyclopentyl-2,3-dihydro-1-oxo-1H-inden-5-yl)oxy)acetic acid: an anion channel blocker	2.46	2	0
rimantadine Rimantadine: An RNA synthesis inhibitor that is used as an antiviral agent in the prophylaxis and treatment of influenza.	5.24	3	1	alkylamine
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.	2.44	2	0	organofluorine compound; piperidines; thiazolopyrimidine	antidepressant; antipsychotic agent; anxiolytic drug; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; serotonergic antagonist
4-(3-butoxy-4-methoxybenzyl)-2-imidazolidinone 4-(3-Butoxy-4-methoxybenzyl)-2-imidazolidinone: Inhibitor of phosphodiesterases.	1.96	1	0	methoxybenzenes
rolipram [no description available]	3.22	6	0	pyrrolidin-2-ones	antidepressant; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor
safrole Safrole: A member of the BENZODIOXOLES that is a constituent of several VOLATILE OILS, notably SASSAFRAS oil. It is a precursor in the synthesis of the insecticide PIPERONYL BUTOXIDE and the drug N-methyl-3,4-methylenedioxyamphetamine (MDMA).. safrole : A member of the class of benzodioxoles that is 1,3-benzodioxole which is substituted by an allyl group at position 5. It is found in several plants, including black pepper, cinnamon and nutmeg, and is present in several essential oils, notably that of sassafras. It has insecticidal properties and has been used as a topical antiseptic. Although not thought to pose a significant carcinogenic risk to humans, findings of weak carcinogenicity in rats have resulted in the banning of its (previously widespread) use in perfumes and soaps, and as a food additive.	1.95	1	0	benzodioxoles	flavouring agent; insecticide; metabolite; plant metabolite
sanguinarine benzophenanthridine alkaloid : A specific group of isoquinoline alkaloids that occur only in higher plants and are constituents mainly of the Papaveraceae family.	3.59	8	0	alkaloid antibiotic; benzophenanthridine alkaloid; botanical anti-fungal agent
sodium fluoride [no description available]	2.07	1	0	fluoride salt	mutagen
iodoacetic acid Iodoacetic Acid: A derivative of ACETIC ACID that contains one IODINE atom attached to its methyl group.. iodoacetic acid : A haloacetic acid that is acetic acid in which one of the hydrogens of the methyl group is replaced by an iodine atom.	1.99	1	0	haloacetic acid; organoiodine compound	alkylating agent
spiperone Spiperone: A spiro butyrophenone analog similar to HALOPERIDOL and other related compounds. It has been recommended in the treatment of SCHIZOPHRENIA.. spiperone : An azaspiro compound that is 1,3,8-triazaspiro[4.5]decane which is substituted at positions 1, 4, and 8 by phenyl, oxo, and 4-(p-fluorophenyl)-4-oxobutyl groups, respectively.	2.01	1	0	aromatic ketone; azaspiro compound; organofluorine compound; piperidines; tertiary amino compound	alpha-adrenergic antagonist; antipsychotic agent; dopaminergic antagonist; psychotropic drug; serotonergic antagonist
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.	3.26	6	0	long-chain fatty acid; saturated fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; human metabolite; plant metabolite
succinylacetone succinylacetone: inhibitor of heme biosynthesis. 4,6-dioxoheptanoic acid : A dioxo monocarboxylic acid that is heptanoic acid in which oxo groups replace the hydrogens at positions 4 and 6. It is an abnormal metabolite of the tyrosine metabolic pathway and a marker for type 1 tyrosinaemia.	1.98	1	0	beta-diketone; dioxo monocarboxylic acid	human metabolite
sulfanilamide [no description available]	1.93	1	0	substituted aniline; sulfonamide antibiotic; sulfonamide	antibacterial agent; drug allergen; EC 4.2.1.1 (carbonic anhydrase) inhibitor
sulforaphane sulforaphane: from Cardaria draba L.. sulforaphane : An isothiocyanate having a 4-(methylsulfinyl)butyl group attached to the nitrogen.	3.03	4	0	isothiocyanate; sulfoxide	antineoplastic agent; antioxidant; EC 3.5.1.98 (histone deacetylase) inhibitor; plant metabolite
suramin Suramin: A polyanionic compound with an unknown mechanism of action. It is used parenterally in the treatment of African trypanosomiasis and it has been used clinically with diethylcarbamazine to kill the adult Onchocerca. (From AMA Drug Evaluations Annual, 1992, p1643) It has also been shown to have potent antineoplastic properties.. suramin : A member of the class of phenylureas that is urea in which each of the amino groups has been substituted by a 3-({2-methyl-5-[(4,6,8-trisulfo-1-naphthyl)carbamoyl]phenyl}carbamoyl)phenyl group. An activator of both the rabbit skeletal muscle RyR1 and sheep cardiac RyR2 isoform ryanodine receptor channels, it has been used for the treatment of human African trypanosomiasis for over 100 years.	2.93	4	0	naphthalenesulfonic acid; phenylureas; secondary carboxamide	angiogenesis inhibitor; antinematodal drug; antineoplastic agent; apoptosis inhibitor; EC 2.7.11.13 (protein kinase C) inhibitor; GABA antagonist; GABA-gated chloride channel antagonist; purinergic receptor P2 antagonist; ryanodine receptor agonist; trypanocidal drug
tegafur [no description available]	2.08	1	0	organohalogen compound; pyrimidines
temozolomide [no description available]	2.31	1	0	imidazotetrazine; monocarboxylic acid amide; triazene derivative	alkylating agent; antineoplastic agent; prodrug
tempol-h TEMPOL-H: hydroxylamine (protonated, reduced) form of TEMPOL; a N-hydroxyl form of LASTAR A; TEMPOL is paramagnetic radical used in NMR as SPIN LABELS whereas TEMPOL-H is not. 4-hydroxy-TEMPO : A member of the class of aminoxyls that is TEMPO carrying a hydroxy substituent at position 4. It is a radical scavenger which exhibits anti-inflammatory and analgesic properties.	2.02	1	0
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.	1.99	1	0	phenylethanolamines; resorcinols	anti-asthmatic drug; beta-adrenergic agonist; bronchodilator agent; EC 3.1.1.7 (acetylcholinesterase) inhibitor; hypoglycemic agent; sympathomimetic agent; tocolytic agent
tetraethylammonium Tetraethylammonium: A potassium-selective ion channel blocker. (From J Gen Phys 1994;104(1):173-90)	2.43	2	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.	2.04	1	0	dimethylxanthine	adenosine receptor antagonist; bronchodilator agent; food component; human blood serum metabolite; mouse metabolite; plant metabolite; vasodilator agent
thiabendazole Tresaderm: dermatologic soln containing dexamethasone, thiabendazole & neomycin sulfate	1.95	1	0	1,3-thiazoles; benzimidazole fungicide; benzimidazoles	antifungal agrochemical; antinematodal drug
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).	1.93	1	0	aziridines
tipepidine tipepidine: RN given refers to parent cpd	3.15	1	0	piperidines
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.	3.46	8	0	N-sulfonylurea	human metabolite; hypoglycemic agent; insulin secretagogue; potassium channel blocker
tremorine [no description available]	1.94	1	0	N-alkylpyrrolidine
triflupromazine Triflupromazine: A phenothiazine used as an antipsychotic agent and as an antiemetic.. triflupromazine : A member of the class of phenothiazines that is 10H-phenothiazine having a trifluoromethyl subsitituent at the 2-position and a 3-(dimethylamino)propyl group at the N-10 position.	2.35	2	0	organofluorine compound; phenothiazines; tertiary amine	anticoronaviral agent; antiemetic; dopaminergic antagonist; first generation antipsychotic
trihexyphenidyl Trihexyphenidyl: One of the centrally acting MUSCARINIC ANTAGONISTS used for treatment of PARKINSONIAN DISORDERS and drug-induced extrapyramidal movement disorders and as an antispasmodic.	3.2	6	0	amine
tripelennamine Tripelennamine: A histamine H1 antagonist with low sedative action but frequent gastrointestinal irritation. It is used to treat ASTHMA; HAY FEVER; URTICARIA; and RHINITIS; and also in veterinary applications. Tripelennamine is administered by various routes, including topically.	1.94	1	0	aromatic amine
troglitazone Troglitazone: A chroman and thiazolidinedione derivative that acts as a PEROXISOME PROLIFERATOR-ACTIVATED RECEPTORS (PPAR) agonist. It was formerly used in the treatment of TYPE 2 DIABETES MELLITUS, but has been withdrawn due to hepatotoxicity.	2.43	2	0	chromanes; thiazolidinone	anticoagulant; anticonvulsant; antineoplastic agent; antioxidant; EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor; ferroptosis inhibitor; hypoglycemic agent; platelet aggregation inhibitor; vasodilator agent
tyramine [no description available]	2.25	1	0	monoamine molecular messenger; primary amino compound; tyramines	EC 3.1.1.8 (cholinesterase) inhibitor; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter
tyrphostin a9 [no description available]	3.12	1	0	alkylbenzene	geroprotector
urethane [no description available]	2.9	4	0	carbamate ester	fungal metabolite; mutagen
vigabatrin [no description available]	2.94	4	0	gamma-amino acid	anticonvulsant; EC 2.6.1.19 (4-aminobutyrate--2-oxoglutarate transaminase) inhibitor
vinca Vinca: A plant genus of the family Apocynaceae.	2.54	2	0	alkaloid
w 7 W 7: RN given refers to parent cpd; structure; calmodulin antagonist	2.13	1	0
zinc chloride zinc chloride: RN given refers to parent cpd. zinc dichloride : A compound of zinc and chloride ions in the ratio 1:2. It exists in four crystalline forms, in each of which the Zn(2+) ions are trigonal planar coordinated to four chloride ions.	1.99	1	0	inorganic chloride; zinc molecular entity	astringent; disinfectant; EC 5.3.3.5 (cholestenol Delta-isomerase) inhibitor; Lewis acid
zolpidem Zolpidem: An imidazopyridine derivative and short-acting GABA-A receptor agonist that is used for the treatment of INSOMNIA.. zolpidem : An imidazo[1,2-a]pyridine compound having a 4-tolyl group at the 2-position, an N,N-dimethylcarbamoylmethyl group at the 3-position and a methyl substituent at the 6-position.	3.45	1	1	imidazopyridine	central nervous system depressant; GABA agonist; sedative
mitomycin Mitomycin: An antineoplastic antibiotic produced by Streptomyces caespitosus. It is one of the bi- or tri-functional ALKYLATING AGENTS causing cross-linking of DNA and inhibition of DNA synthesis.. mitomycin : A family of aziridine-containing natural products isolated from Streptomyces caespitosus or Streptomyces lavendulae.	4.31	6	0	mitomycin	alkylating agent; antineoplastic agent
corticosterone [no description available]	3.62	8	0	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone	human metabolite; mouse metabolite
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.	2.48	2	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.	1.94	1	0	16alpha-hydroxy steroid; 17beta-hydroxy steroid; 3-hydroxy steroid	estrogen; human metabolite; human xenobiotic metabolite; mouse metabolite
lysergic acid diethylamide Lysergic Acid Diethylamide: Semisynthetic derivative of ergot (Claviceps purpurea). It has complex effects on serotonergic systems including antagonism at some peripheral serotonin receptors, both agonist and antagonist actions at central nervous system serotonin receptors, and possibly effects on serotonin turnover. It is a potent hallucinogen, but the mechanisms of that effect are not well understood.. lysergic acid diethylamide : An ergoline alkaloid arising from formal condensation of lysergic acid with diethylamine.	2.35	2	0	ergoline alkaloid; monocarboxylic acid amide; organic heterotetracyclic compound	dopamine agonist; hallucinogen; serotonergic agonist
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.	3.05	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.	2.88	4	0	imidazoles; phenols; substituted aniline; tertiary amino compound	alpha-adrenergic antagonist; vasodilator agent
sorbitol D-glucitol : The D-enantiomer of glucitol (also known as D-sorbitol).	3.95	13	0	glucitol	cathartic; Escherichia coli metabolite; food humectant; human metabolite; laxative; metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite; sweetening agent
thymidine [no description available]	3.37	7	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite
piperonyl butoxide [no description available]	2.1	1	0	benzodioxoles	pesticide synergist
benzimidazole 1H-benzimidazole : The 1H-tautomer of benzimidazole.	2.69	2	0	benzimidazole; polycyclic heteroarene
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.	4.21	5	0	4-hydroxyproline; L-alpha-amino acid zwitterion	human metabolite; mouse metabolite; plant metabolite
3,4-dichlorobenzoic acid 3,4-dichlorobenzoic acid: structure given in first source. 3,4-dichlorobenzoic acid : A chlorobenzoic acid carrying chloro substituents at positions 3 and 4.	2.07	1	0	chlorobenzoic acid
thyroxine Thyroxine: The major hormone derived from the thyroid gland. Thyroxine is synthesized via the iodination of tyrosines (MONOIODOTYROSINE) and the coupling of iodotyrosines (DIIODOTYROSINE) in the THYROGLOBULIN. Thyroxine is released from thyroglobulin by proteolysis and secreted into the blood. Thyroxine is peripherally deiodinated to form TRIIODOTHYRONINE which exerts a broad spectrum of stimulatory effects on cell metabolism.. thyroxine : An iodothyronine compound having iodo substituents at the 3-, 3'-, 5- and 5'-positions.	3.22	6	0	2-halophenol; iodophenol; L-phenylalanine derivative; non-proteinogenic L-alpha-amino acid; thyroxine zwitterion; thyroxine	antithyroid drug; human metabolite; mouse metabolite; thyroid hormone
dextroamphetamine Dextroamphetamine: The d-form of AMPHETAMINE. It is a central nervous system stimulant and a sympathomimetic. It has also been used in the treatment of narcolepsy and of attention deficit disorders and hyperactivity in children. Dextroamphetamine has multiple mechanisms of action including blocking uptake of adrenergics and dopamine, stimulating release of monamines, and inhibiting monoamine oxidase. It is also a drug of abuse and a psychotomimetic.. (S)-amphetamine : A 1-phenylpropan-2-amine that has S configuration.	1.95	1	0	1-phenylpropan-2-amine	adrenergic agent; adrenergic uptake inhibitor; dopamine uptake inhibitor; dopaminergic agent; neurotoxin; sympathomimetic agent
carbachol Carbachol: A slowly hydrolyzed CHOLINERGIC AGONIST that acts at both MUSCARINIC RECEPTORS and NICOTINIC RECEPTORS.	3.07	5	0	ammonium salt; carbamate ester	cardiotonic drug; miotic; muscarinic agonist; nicotinic acetylcholine receptor agonist; non-narcotic analgesic
aldosterone [no description available]	5.42	8	2	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
estrone Hydroxyestrones: Estrone derivatives substituted with one or more hydroxyl groups in any position. They are important metabolites of estrone and other estrogens.	1.94	1	0	17-oxo steroid; 3-hydroxy steroid; phenolic steroid; phenols	antineoplastic agent; bone density conservation agent; estrogen; human metabolite; mouse metabolite
androsterone [no description available]	3.05	1	0	17-oxo steroid; 3alpha-hydroxy steroid; androstanoid; C19-steroid	androgen; anticonvulsant; human blood serum metabolite; human metabolite; human urinary metabolite; mouse metabolite; pheromone
dehydroepiandrosterone Dehydroepiandrosterone: A major C19 steroid produced by the ADRENAL CORTEX. It is also produced in small quantities in the TESTIS and the OVARY. Dehydroepiandrosterone (DHEA) can be converted to TESTOSTERONE; ANDROSTENEDIONE; ESTRADIOL; and ESTRONE. Most of DHEA is sulfated (DEHYDROEPIANDROSTERONE SULFATE) before secretion.. dehydroepiandrosterone : An androstanoid that is androst-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 17. It is a naturally occurring steroid hormone produced by the adrenal glands.	2.06	1	0	17-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; androstanoid	androgen; human metabolite; mouse metabolite
1,2,5,6-dibenzanthracene 1,2,5,6-dibenzanthracene: RN given refers to parent cpd	2.04	1	0	ortho-fused polycyclic arene	mutagen
dichlororibofuranosylbenzimidazole Dichlororibofuranosylbenzimidazole: An RNA polymerase II transcriptional inhibitor. This compound terminates transcription prematurely by selective inhibition of RNA synthesis. It is used in research to study underlying mechanisms of cellular regulation.	1.98	1	0
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.	1.94	1	0	penicillin allergen; penicillin	antibacterial drug; drug allergen; epitope
idoxuridine [no description available]	1.97	1	0	organoiodine compound; pyrimidine 2'-deoxyribonucleoside	antiviral drug; DNA synthesis inhibitor
metaraminol Metaraminol: A sympathomimetic agent that acts predominantly at alpha-1 adrenergic receptors. It has been used primarily as a vasoconstrictor in the treatment of HYPOTENSION.. metaraminol : A member of the class of phenylethanolamines that is 2-amino-1-phenylethanol substituted by a methyl group at position 2 and a phenolic hydroxy group at position 1. A sympathomimetic agent , it is used in the treatment of hypotension.	2.34	2	0	phenylethanolamines	alpha-adrenergic agonist; sympathomimetic agent; vasoconstrictor agent
pilocarpine Pilocarpine: A slowly hydrolyzed muscarinic agonist with no nicotinic effects. Pilocarpine is used as a miotic and in the treatment of glaucoma.. (+)-pilocarpine : The (+)-enantiomer of pilocarpine.	5.17	9	0	pilocarpine	antiglaucoma drug
pentylenetetrazole Pentylenetetrazole: A pharmaceutical agent that displays activity as a central nervous system and respiratory stimulant. It is considered a non-competitive GAMMA-AMINOBUTYRIC ACID antagonist. Pentylenetetrazole has been used experimentally to study seizure phenomenon and to identify pharmaceuticals that may control seizure susceptibility.. pentetrazol : An organic heterobicyclic compound that is 1H-tetrazole in which the hydrogens at positions 1 and 5 are replaced by a pentane-1,5-diyl group. A central and respiratory stimulant, it was formerly used for the treatment of cough and other respiratory tract disorders, cardiovascular disorders including hypotension, and pruritis.	2.68	3	0	organic heterobicyclic compound; organonitrogen heterocyclic compound
triiodothyronine Triiodothyronine: A T3 thyroid hormone normally synthesized and secreted by the thyroid gland in much smaller quantities than thyroxine (T4). Most T3 is derived from peripheral monodeiodination of T4 at the 5' position of the outer ring of the iodothyronine nucleus. The hormone finally delivered and used by the tissues is mainly T3.. 3,3',5-triiodo-L-thyronine : An iodothyronine compound having iodo substituents at the 3-, 3'- and 5-positions. Although some is produced in the thyroid, most of the 3,3',5-triiodo-L-thyronine in the body is generated by mono-deiodination of L-thyroxine in the peripheral tissues. Its metabolic activity is about 3 to 5 times that of L-thyroxine. The sodium salt is used in the treatment of hypothyroidism.	2.89	4	0	2-halophenol; amino acid zwitterion; iodophenol; iodothyronine	human metabolite; mouse metabolite; thyroid hormone
diethylnitrosamine Diethylnitrosamine: A nitrosamine derivative with alkylating, carcinogenic, and mutagenic properties.. N-nitrosodiethylamine : A nitrosamine that is N-ethylethanamine substituted by a nitroso group at the N-atom.	1.95	1	0	nitrosamine	carcinogenic agent; hepatotoxic agent; mutagen
isoflurophate Isoflurophate: A di-isopropyl-fluorophosphate which is an irreversible cholinesterase inhibitor used to investigate the NERVOUS SYSTEM.	2.86	4	0	dialkyl phosphate
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.	3.12	5	0	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
cantharidin Cantharidin: A toxic compound, isolated from the Spanish fly or blistering beetle (Lytta (Cantharis) vesicatoria) and other insects. It is a potent and specific inhibitor of protein phosphatases 1 (PP1) and 2A (PP2A). This compound can produce severe skin inflammation, and is extremely toxic if ingested orally.. cantharidin : A monoterpenoid with an epoxy-bridged cyclic dicarboxylic anhydride structure secreted by many species of blister beetle, and most notably by the Spanish fly, Lytta vesicatoria. Natural toxin inhibitor of protein phosphatases 1 and 2A.	4.82	10	0	cyclic dicarboxylic anhydride; monoterpenoid	EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; herbicide
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.	10.55	23	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.	3.7	10	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.	2.04	1	0	ortho-fused polycyclic arene; tetraphenes
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.	3.79	11	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.	6.08	16	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.	5.38	19	0	aspartate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; lysine; organic molecular entity; proteinogenic amino acid	algal metabolite; anticonvulsant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
allyl isothiocyanate allyl isothiocyanate: used in the manufacture of flavors, war gases; medical use as a counterirritant; structure. allyl isothiocyanate : An isothiocyanate with the formula CH2=CHCH2N=C=S. A colorless oil with boiling point 152degreeC, it is responsible for the pungent taste of mustard, horseradish, and wasabi.	2.06	1	0	alkenyl isothiocyanate; isothiocyanate	antimicrobial agent; antineoplastic agent; apoptosis inducer; lachrymator; 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.	3.87	12	0	pseudohalide anion	EC 1.9.3.1 (cytochrome c oxidase) inhibitor
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.	2.88	4	0	carbamate ester; indole alkaloid	antidote to curare poisoning; EC 3.1.1.8 (cholinesterase) inhibitor; miotic
sulfamic acid sulfamic acid: standard in alkalimetry; RN given refers to parent cpd; structure. sulfamic acid : The simplest of the sulfamic acids consisting of a single sulfur atom covalently bound by single bonds to hydroxy and amino groups and by double bonds to two oxygen atoms.	2	1	0	sulfamic acids
sucrose Saccharum: A plant genus of the family POACEAE widely cultivated in the tropics for the sweet cane that is processed into sugar.	5.32	51	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.	2.64	3	0	17-hydroxy steroid; 3-hydroxy steroid; terminal acetylenic compound	xenoestrogen
testosterone propionate Testosterone Propionate: An ester of TESTOSTERONE with a propionate substitution at the 17-beta position.. androgen : A sex hormone that stimulates or controls the development and maintenance of masculine characteristics in vertebrates by binding to androgen receptors.	2.15	1	0	steroid ester
apomorphine Apomorphine: A derivative of morphine that is a dopamine D2 agonist. It is a powerful emetic and has been used for that effect in acute poisoning. It has also been used in the diagnosis and treatment of parkinsonism, but its adverse effects limit its use.	2.67	3	0	aporphine alkaloid	alpha-adrenergic drug; antidyskinesia agent; antiparkinson drug; dopamine agonist; emetic; serotonergic drug
adenosine diphosphate Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.	3.47	8	0	adenosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	fundamental metabolite; human metabolite
2,3,4,6-tetrachlorophenol 2,3,4,6-tetrachlorophenol: RN given refers to parent cpd; see also record for tetrachlorophenol with locants for chloro groups not specified. 2,3,4,6-tetrachlorophenol : A tetrachlorophenol in which the chlorines are located at positions 2, 3, 4, and 6.	2.31	1	0	tetrachlorophenol	xenobiotic metabolite
uridine [no description available]	3.37	7	0	uridines	drug metabolite; fundamental metabolite; human metabolite
bromodeoxyuridine Bromodeoxyuridine: A nucleoside that substitutes for thymidine in DNA and thus acts as an antimetabolite. It causes breaks in chromosomes and has been proposed as an antiviral and antineoplastic agent. It has been given orphan drug status for use in the treatment of primary brain tumors.	3.08	5	0	pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent
galactose galactopyranose : The pyranose form of galactose.	4.18	17	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.	2.77	3	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.	7.01	14	2	phenols; phenylethanolamines; secondary amino compound	alpha-adrenergic agonist; cardiotonic drug; mydriatic agent; nasal decongestant; protective agent; sympathomimetic agent; vasoconstrictor agent
benzoxazolone benzoxazolone: RN given refers to parent cpd; structure. 2-benzoxazolinone : A member of the class of benzoxazoles that is 2,3-dihydro-1,3-benzoxazole carrying an oxo group at position 2.	2.07	1	0	benzoxazole	allelochemical; phytoalexin
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	2.68	3	0	amino acid zwitterion; dopa; L-tyrosine derivative; non-proteinogenic L-alpha-amino acid	allelochemical; antidyskinesia agent; antiparkinson drug; dopaminergic agent; hapten; human metabolite; mouse metabolite; neurotoxin; plant growth retardant; plant metabolite; prodrug
edetic acid Edetic Acid: A chelating agent that sequesters a variety of polyvalent cations such as CALCIUM. It is used in pharmaceutical manufacturing and as a food additive.	2.89	4	0	ethylenediamine derivative; polyamino carboxylic acid; tetracarboxylic acid	anticoagulant; antidote; chelator; copper chelator; geroprotector
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.	5	9	1	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.	5.5	21	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.	2.37	2	0	amine; thiol	geroprotector; human metabolite; mouse metabolite; radiation protective agent
phlorhizin [no description available]	2.43	2	0	aryl beta-D-glucoside; dihydrochalcones; monosaccharide derivative	antioxidant; plant metabolite
methoxamine Methoxamine: An alpha-1 adrenergic agonist that causes prolonged peripheral VASOCONSTRICTION.. methoxamine : An amphetamine in which the parent 1-phenylpropan-2-amine skeleton is substituted at position 1 with an hydroxy group and the phenyl ring is 2- and 5-substituted with methoxy groups. It is an antihypotensive agent (pressor), an agonist acting directly at alpha-adrenoceptors with selectivity for the alpha-1 adrenoceptor subtype similar to phenylephrine .	1.94	1	0	amphetamines	alpha-adrenergic agonist; antihypotensive agent
adenosine monophosphate Adenosine Monophosphate: Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position.	3.17	5	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
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.	8	41	1	amino acid zwitterion; L-alpha-amino acid; leucine; proteinogenic amino acid; pyruvate family amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
ethyl methanesulfonate Ethyl Methanesulfonate: An antineoplastic agent with alkylating properties. It also acts as a mutagen by damaging DNA and is used experimentally for that effect.. ethyl methanesulfonate : A methanesulfonate ester resulting from the formal condensation of methanesulfonic acid with ethanol.	3.1	5	0	methanesulfonate ester	alkylating agent; antineoplastic agent; carcinogenic agent; genotoxin; mutagen; teratogenic agent
aniline [no description available]	4.05	5	0	anilines; primary arylamine
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.	2.49	2	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.	2.72	3	0	17-oxo steroid; 3-oxo-Delta(4) steroid; androstanoid	androgen; Daphnia magna metabolite; human metabolite; mouse metabolite
uridine triphosphate Uridine Triphosphate: Uridine 5'-(tetrahydrogen triphosphate). A uracil nucleotide containing three phosphate groups esterified to the sugar moiety.	2.03	1	0	pyrimidine ribonucleoside 5'-triphosphate; uridine 5'-phosphate	Escherichia coli metabolite; mouse metabolite
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.	1.98	1	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.	8.38	42	1	aspartate family amino acid; L-alpha-amino acid; methionine zwitterion; methionine; proteinogenic amino acid	antidote to paracetamol poisoning; human metabolite; micronutrient; mouse metabolite; nutraceutical
1,2-dipalmitoylphosphatidylcholine 1,2-Dipalmitoylphosphatidylcholine: Synthetic phospholipid used in liposomes and lipid bilayers to study biological membranes. It is also a major constituent of PULMONARY SURFACTANTS.	1.97	1	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.	9.83	33	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; phenylalanine; proteinogenic amino acid	algal metabolite; EC 3.1.3.1 (alkaline phosphatase) inhibitor; Escherichia coli metabolite; human xenobiotic metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
colchicine (S)-colchicine : A colchicine that has (S)-configuration. It is a secondary metabolite, has anti-inflammatory properties and is used to treat gout, crystal-induced joint inflammation, familial Mediterranean fever, and many other conditions.	6.72	18	1	alkaloid; colchicine	anti-inflammatory agent; gout suppressant; mutagen
cytidine [no description available]	3.27	6	0	cytidines	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
cycloheximide Cycloheximide: Antibiotic substance isolated from streptomycin-producing strains of Streptomyces griseus. It acts by inhibiting elongation during protein synthesis.. cycloheximide : A dicarboximide that is 4-(2-hydroxyethyl)piperidine-2,6-dione in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 3,5-dimethyl-2-oxocyclohexyl group. It is an antibiotic produced by the bacterium Streptomyces griseus.	5.64	76	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.	3.64	9	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.	2.91	4	0	chloromethanes; one-carbon compound	carcinogenic agent; central nervous system drug; inhalation anaesthetic; non-polar solvent; refrigerant
sodium citrate, anhydrous Sodium Citrate: Sodium salts of citric acid that are used as buffers and food preservatives. They are used medically as anticoagulants in stored blood, and for urine alkalization in the prevention of KIDNEY STONES.. sodium citrate : The trisodium salt of citric acid.	2.08	1	0	organic sodium salt	anticoagulant; flavouring agent
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.	2.37	2	0	beta-lactam antibiotic; penicillin allergen; penicillin	antibacterial drug
mannitol [no description available]	3.98	13	0	mannitol	allergen; antiglaucoma drug; compatible osmolytes; Escherichia coli metabolite; food anticaking agent; food bulking agent; food humectant; food stabiliser; food thickening agent; hapten; metabolite; osmotic diuretic; sweetening agent
cytarabine [no description available]	2.53	2	0	beta-D-arabinoside; monosaccharide derivative; pyrimidine nucleoside	antimetabolite; antineoplastic agent; antiviral agent; immunosuppressive agent
ornithine Ornithine: An amino acid produced in the urea cycle by the splitting off of urea from arginine.. ornithine : An alpha-amino acid that is pentanoic acid bearing two amino substituents at positions 2 and 5.	3.08	5	0	non-proteinogenic L-alpha-amino acid; ornithine	algal metabolite; hepatoprotective agent; mouse metabolite
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.	2.36	2	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.	3.05	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
n-pentanol n-pentanol: RN given refers to parent cpd. pentan-1-ol : A short-chain primary fatty alcohol that is pentane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It has been isolated from Melicope ptelefolia.	5.37	10	0	pentanol; short-chain primary fatty alcohol	human metabolite; plant metabolite
1,1,1-trichloroethane Trichloroethanes: Chlorinated ethanes which are used extensively as industrial solvents. They have been utilized in numerous home-use products including spot remover preparations and inhalant decongestant sprays. These compounds cause central nervous system and cardiovascular depression and are hepatotoxic. Include 1,1,1- and 1,1,2-isomers.. 1,1,1-trichloroethane : A member of the class of chloroethanes carrying three chloro substituents at position 1.	2.04	1	0	chloroethanes	polar solvent
medroxyprogesterone acetate [no description available]	2.08	1	0	20-oxo steroid; 3-oxo-Delta(4) steroid; acetate ester; corticosteroid; steroid ester	adjuvant; androgen; antineoplastic agent; antioxidant; female contraceptive drug; inhibitor; progestin; synthetic oral contraceptive
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.	10.48	16	1	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.	3.49	8	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
cordycepin [no description available]	2.25	1	0	3'-deoxyribonucleoside; adenosines	antimetabolite; nucleoside antibiotic
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.	5.25	16	0	erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; tryptophan zwitterion; tryptophan	antidepressant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
isoleucine Isoleucine: An essential branched-chain aliphatic amino acid found in many proteins. It is an isomer of LEUCINE. It is important in hemoglobin synthesis and regulation of blood sugar and energy levels.. isoleucine : A 2-amino-3-methylpentanoic acid having either (2R,3R)- or (2S,3S)-configuration.. L-isoleucine : The L-enantiomer of isoleucine.	9.37	172	0	aspartate family amino acid; isoleucine; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
4-chlorobenzoic acid 4-chlorobenzoic acid: RN given refers to parent cpd. 4-chlorobenzoic acid : A monochlorobenzoic acid carrying a chloro substituent at position 4.	2.07	1	0	monochlorobenzoic acid	bacterial xenobiotic 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.	11.85	12	1	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
ethane Ethane: A two carbon alkane with the formula H3C-CH3.. ethane : An alkane comprising of two carbon atoms.	2.34	2	0	alkane; gas molecular entity	plant metabolite; refrigerant
ethylene Plastipore: high density polyethylene sponge biocompatible material; used as posts in dental bridges	12.5	630	0	alkene; gas molecular entity	plant hormone; refrigerant
acetylene [no description available]	8.91	12	0	alkyne; gas molecular entity; terminal acetylenic compound
methyl iodide methyl iodide: RN given refers to unlabeled cpd with MF of CH3-I. iodomethane : A member of the class of iodomethanes that is methane in which one of the hydrogens is replaced by iodine.	2.07	1	0	iodomethanes; methyl halides	fumigant insecticide
methylamine methyl group : An alkyl group that is the univalent group derived from methane by removal of a hydrogen atom.	3.23	6	0	methylamines; one-carbon compound; primary aliphatic amine	mouse metabolite
boranes Boranes: The collective name for the boron hydrides, which are analogous to the alkanes and silanes. Numerous boranes are known. Some have high calorific values and are used in high-energy fuels. (From Grant & Hackh's Chemical Dictionary, 5th ed). borane : The simplest borane, consisting of a single boron atom carrying three hydrogens.. boranes : The molecular hydrides of boron.	3.77	10	0	boranes; mononuclear parent hydride
propane Propane: A three carbon alkane with the formula H3CCH2CH3.	2.67	3	0	alkane; gas molecular entity	food propellant
ethyl chloride Ethyl Chloride: A gas that condenses under slight pressure. Because of its low boiling point ethyl chloride sprayed on skin produces an intense cold by evaporation. Cold blocks nerve conduction. Ethyl chloride has been used in surgery but is primarily used to relieve local pain in sports medicine.. chloroethane : The simplest and least toxic member of the class of chloroethanes, that is ethane in which a single hydrogen is substituted by a chlorine. A colourless gas at room temperature and pressure (boiling point 12degreeC), it is used as a mild topical anaesthetic to numb the skin prior to ear piercing, skin biopsies, etc., and is also used in the treatment of sports injuries. It was formerly used in the production of tetraethyllead.	2.04	1	0	chloroethanes	antipruritic drug; inhalation anaesthetic; local anaesthetic
acetonitrile acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.	2.11	1	0	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
methylene chloride Methylene Chloride: A chlorinated hydrocarbon that has been used as an inhalation anesthetic and acts as a narcotic in high concentrations. Its primary use is as a solvent in manufacturing and food technology.. dichloromethane : A member of the class of chloromethanes that is methane in which two of the hydrogens have been replaced by chlorine. A dense, non-flammible colourless liquid at room temperature (b.p. 40degreeC, d = 1.33) which is immiscible with water, it is widely used as a solvent, a paint stripper, and for the removal of caffeine from coffee and tea.	2.99	4	0	chloromethanes; volatile organic compound	carcinogenic agent; polar aprotic solvent; refrigerant
cyclopropane cyclopropane : A cycloalkane composed of three carbon atoms to form a ring.	10.14	8	0	cycloalkane; cyclopropanes	inhalation anaesthetic
ethylene oxide Ethylene Oxide: A colorless and flammable gas at room temperature and pressure. Ethylene oxide is a bactericidal, fungicidal, and sporicidal disinfectant. It is effective against most micro-organisms, including viruses. It is used as a fumigant for foodstuffs and textiles and as an agent for the gaseous sterilization of heat-labile pharmaceutical and surgical materials. (From Reynolds, Martindale The Extra Pharmacopoeia, 30th ed, p794). oxirane : A saturated organic heteromonocyclic parent that is a three-membered heterocycle of two carbon atoms and one oxygen atom.	2.93	4	0	gas molecular entity; oxacycle; saturated organic heteromonocyclic parent	allergen; mouse metabolite; mutagen
boron trifluoride [no description available]	2.02	1	0	boron fluoride	NMR chemical shift reference compound
trichlorofluoromethane trichlorofluoromethane: refrigerant, aerosol propellant; RN given refers to parent cpd; structure. trichlorofluoromethane : A one-carbon compound that is methane in which the hydrogens have been replaced by three chlorine and one fluorine atom.	2.04	1	0	chlorofluorocarbon; halomethane	environmental contaminant; NMR chemical shift reference compound; NMR solvent; refrigerant
methanesulfonic acid [no description available]	1.94	1	0	alkanesulfonic acid; one-carbon compound	Escherichia coli metabolite
tert-butylhydroperoxide tert-Butylhydroperoxide: A direct-acting oxidative stress-inducing agent used to examine the effects of oxidant stress on Ca(2+)-dependent signal transduction in vascular endothelial cells. It is also used as a catalyst in polymerization reactions and to introduce peroxy groups into organic molecules.. tert-butyl hydroperoxide : An alkyl hydroperoxide in which the alkyl group is tert-butyl. It is widely used in a variety of oxidation processes.	2.15	1	0	alkyl hydroperoxide	antibacterial agent; oxidising agent
pivalic acid pivalic acid: RN given refers to parent cpd; structure. pivalic acid : A branched, short-chain fatty acid composed of propanoic acid having two methyl substituents at the 2-position.	2.01	1	0	branched-chain saturated fatty acid; methyl-branched fatty acid; short-chain fatty acid
pentachloroethane [no description available]	2.04	1	0	chloroethanes	non-polar solvent
trichloroacetic acid Trichloroacetic Acid: A strong acid used as a protein precipitant in clinical chemistry and also as a caustic for removing warts.. trichloroacetic acid : A monocarboxylic acid that is acetic acid in which all three methyl hydrogens are substituted by chlorine.	2.03	1	0	monocarboxylic acid; organochlorine compound	carcinogenic agent; metabolite; mouse metabolite
trifluoroacetic acid Trifluoroacetic Acid: A very strong halogenated derivative of acetic acid. It is used in acid catalyzed reactions, especially those where an ester is cleaved in peptide synthesis.. trifluoroacetic acid : A monocarboxylic acid that is the trifluoro derivative of acetic acid.	2.72	3	0	fluoroalkanoic acid	human xenobiotic metabolite; NMR chemical shift reference compound; reagent
pinacol pinacol : A glycol that is ethylene glycol in which all four methylene hydrogens have been replaced by methyl groups.	2.17	1	0	glycol
triamcinolone acetonide Triamcinolone Acetonide: An esterified form of TRIAMCINOLONE. It is an anti-inflammatory glucocorticoid used topically in the treatment of various skin disorders. Intralesional, intramuscular, and intra-articular injections are also administered under certain conditions.. triamcinolone acetonide : A synthetic glucocorticoid that is the 16,17-acetonide of triamcinolone. Used to treat various skin infections.	1.94	1	0	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; cyclic ketal; fluorinated steroid; glucocorticoid; primary alpha-hydroxy ketone	anti-allergic agent; anti-inflammatory drug
gibberellic acid gibberellic acid: RN given refers to (1alpha,2beta,4aalpha,4bbeta,10beta)-isomer; structure. gibberellin A3 : A C19-gibberellin that is a pentacyclic diterpenoid responsible for promoting growth and elongation of cells in plants. Initially identified in Gibberella fujikuroi,it differs from gibberellin A1 in the presence of a double bond between C-3 and C-4.	7.84	56	0	C19-gibberellin; gibberellin monocarboxylic acid; lactone; organic heteropentacyclic compound	mouse metabolite; plant metabolite
phencyclidine Phencyclidine: A hallucinogen formerly used as a veterinary anesthetic, and briefly as a general anesthetic for humans. Phencyclidine is similar to KETAMINE in structure and in many of its effects. Like ketamine, it can produce a dissociative state. It exerts its pharmacological action through inhibition of NMDA receptors (RECEPTORS, N-METHYL-D-ASPARTATE). As a drug of abuse, it is known as PCP and Angel Dust.. phencyclidine : A member of the class of piperidines that is piperidine in which the nitrogen is substituted with a 1-phenylcyclohexyl group. Formerly used as an anaesthetic agent, it exhibits both hallucinogenic and neurotoxic effects.	6.26	11	1	benzenes; piperidines	anaesthetic; neurotoxin; NMDA receptor antagonist; psychotropic drug
caramiphen caramiphen: structure	10.52	96	1	benzenes
hexachlorocyclopentadiene [no description available]	3.56	9	0
dicyclopentadiene [no description available]	1.92	1	0	cyclic olefin
tromethamine Tromethamine: An organic amine proton acceptor. It is used in the synthesis of surface-active agents and pharmaceuticals; as an emulsifying agent for cosmetic creams and lotions, mineral oil and paraffin wax emulsions, as a biological buffer, and used as an alkalizer. (From Merck, 11th ed; Martindale, The Extra Pharmacopoeia, 30th ed, p1424)	1.94	1	0	primary amino compound; triol	buffer
quinic acid (-)-quinic acid : The (-)-enantiomer of quinic acid.	2.48	2	0
azobis(isobutyronitrile) azobis(isobutyronitrile): blowing agent for elastomers & plastics; initiator for free radical reactions; structure	2.07	1	0
linalool linalool: RN given refers to parent cpd without isomeric designation; structure. linalool : A monoterpenoid that is octa-1,6-diene substituted by methyl groups at positions 3 and 7 and a hydroxy group at position 3. It has been isolated from plants like Ocimum canum.	4.47	21	0	monoterpenoid; tertiary alcohol	antimicrobial agent; fragrance; plant metabolite; volatile oil component
isopentane [no description available]	2.46	2	0	alkane	refrigerant
isoprene isoprene: used in manufacture of ''synthetic'' rubber, butyl rubber; copolymer in production of elastomers; structure. isoprene : A hemiterpene with the formula CH2=C(CH3)CH=CH2; the monomer of natural rubber and a common structure motif to the isoprenoids, a large class of other naturally occurring compounds.	4.12	14	0	alkadiene; hemiterpene; volatile organic compound	plant metabolite
isobutyraldehyde isobutyraldehyde : A member of the class of propanals that is propanal substituted by a methyl group at position 2.	2.07	1	0	2-methyl-branched fatty aldehyde; propanals	Saccharomyces cerevisiae metabolite
methacrylaldehyde [no description available]	2.03	1	0	enal
2-butanol 2-butanol: RN given is for parent cpd without isomeric designation. butan-2-ol : A secondary alcohol that is butane substituted by a hydroxy group at position 2.	1.92	1	0	secondary alcohol
3-buten-2-one buten-2-one : A methyl ketone that is butan-2-one with an unsaturation at position 3.	2.47	2	0	enone; methyl ketone
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.	2.04	1	0	chloroethenes	inhalation anaesthetic; mouse metabolite
acrylamide [no description available]	2.06	1	0	acrylamides; N-acylammonia; primary carboxamide	alkylating agent; carcinogenic agent; Maillard reaction product; mutagen; neurotoxin
1,1,2,2-tetrachloroethane 1,1,2,2-tetrachloroethane: see also record for tetrachloroethane. 1,1,2,2-tetrachloroethane : A member of the class of chloroethanes that is ethane substituted by chloro groups at positions 1, 1, 2 and 2.	2.04	1	0	chloroethanes
pantothenic acid Pantothenic Acid: A butyryl-beta-alanine that can also be viewed as pantoic acid complexed with BETA ALANINE. It is incorporated into COENZYME A and protects cells against peroxidative damage by increasing the level of GLUTATHIONE.. pantothenic acid : A member of the class of pantothenic acids that is an amide formed from pantoic acid and beta-alanine.. vitamin B5 : Any member of a group of vitamers that belong to the chemical structural class called pantothenic acids that exhibit biological activity against vitamin B5 deficiency. Deficiency of vitamin B5 is rare due to its widespread distribution in whole grain cereals, legumes and meat. Symptoms associated with vitamin B5 deficiency are difficult to asses since they are subtle and resemble those of other B vitamin deficiencies. The vitamers include (R)-pantothenic acid and its ionized and salt forms.. (R)-pantothenate : A pantothenate that is the conjugate base of (R)-pantothenic acid, obtained by deprotonation of the carboxy group.. (R)-pantothenic acid : A pantothenic acid having R-configuration.	2.37	2	0	pantothenic acid; vitamin B5	antidote to curare poisoning; geroprotector; human blood serum metabolite
camphene camphene : A monoterpene with a bicyclic skeleton that is bicyclo[2.2.1]heptane substituted by geminal methyl groups at position 2 and a methylidene group at position 3. It is a widespread natural product found in many essential oils.	2.11	1	0	carbobicyclic compound; monoterpene	fragrance; plant metabolite
bisphenol a 4,4'-isopropylidene diphenol: stimulates proliferative responses and cytokine productions of murine spleen cells and thymus cells in vitro. bisphenol : By usage, the methylenediphenols, HOC6H4CH2C6H4OH, commonly p,p-methylenediphenol, and their substitution products (generally derived from condensation of two equivalent amounts of a phenol with an aldehyde or ketone). The term also includes analogues in the the methylene (or substituted methylene) group has been replaced by a heteroatom.. bisphenol A : A bisphenol that is 4,4'-methanediyldiphenol in which the methylene hydrogens are replaced by two methyl groups.	5.1	2	1	bisphenol	endocrine disruptor; environmental contaminant; xenobiotic; xenoestrogen
terpin terpene : A hydrocarbon of biological origin having carbon skeleton formally derived from isoprene [CH2=C(CH3)CH=CH2].	2.1	1	0	p-menthane monoterpenoid
alpha-pinene [no description available]	3.31	6	0	pinene	plant metabolite
3-methyl-1,2-cyclopentanedione cyclotene: product of sugar degradation	4.36	6	0
taurocholic acid 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.. taurocholate : An organosulfonate oxoanion that is the conjugate base of taurocholic acid.. taurocholic acid : A bile acid taurine conjugate of cholic acid that usually occurs as the sodium salt of bile in mammals.	2.39	2	0	amino sulfonic acid; bile acid taurine conjugate	human metabolite
1,8-naphthalenedicarboxylic acid anhydride 1,8-naphthalenedicarboxylic acid anhydride: used as seed protector from herbicides	2.02	1	0	cyclic dicarboxylic anhydride
acenaphthene [no description available]	2.04	1	0	acenaphthenes
skatole [no description available]	2.02	1	0	methylindole	human metabolite; mammalian metabolite
methylprednisolone Methylprednisolone: A PREDNISOLONE derivative with similar anti-inflammatory action.. 6alpha-methylprednisolone : The 6alpha-stereoisomer of 6-methylprednisolone.	2.57	2	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.	2.81	3	0	organic heteropentacyclic compound; rotenones	antineoplastic agent; metabolite; mitochondrial NADH:ubiquinone reductase inhibitor; phytogenic insecticide; piscicide; toxin
7,8-dimethyl-10-[(2R,3R,4S)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4-dione [no description available]	2.04	1	0	flavin
(+-)stylopine [no description available]	2.03	1	0
pyocyanine Pyocyanine: Antibiotic pigment produced by Pseudomonas aeruginosa.. pyocyanine : An iminium betaine that is 5-methylphenazin-5-ium which is substituted at position 1 by an oxidanidyl group. An antibiotic pigment produced by Pseudomonas aeruginosa.	2.03	1	0	iminium betaine; phenazines	antibacterial agent; bacterial metabolite; biological pigment; virulence factor
propoxycaine Propoxycaine: A local anesthetic of the ester type that has a rapid onset of action and a longer duration of action than procaine hydrochloride. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1017)	1.95	1	0	benzoate ester
1-naphthoic acid naphthoic acid : An aromatic carboxylic acid that consists of a naphthalene skeleton substituted by one or more carboxy groups.	2.1	1	0	naphthoic acid	bacterial xenobiotic metabolite; fungal xenobiotic metabolite
fluorene [no description available]	2.46	2	0	ortho-fused polycyclic arene; ortho-fused tricyclic hydrocarbon
1-naphthaleneacetic acid 1-naphthaleneacetic acid: a plant growth regulator; RN given refers to parent cpd. naphthylacetic acid : A monocarboxylic acid that is naphthalene substituted by a carboxymethyl group at any position.. 1-naphthaleneacetic acid : A naphthylacetic acid substituted by a carboxymethyl group at position 1.	3.31	6	0	naphthylacetic acid	synthetic auxin
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.	1.94	1	0	penicillin allergen; penicillin
gramine gramine : An aminoalkylindole that is indole carrying a dimethylaminomethyl substituent at postion 3.	2.06	1	0	aminoalkylindole; indole alkaloid; tertiary amino compound	antibacterial agent; antiviral agent; plant metabolite; serotonergic antagonist
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.	3.48	2	0	penicillanic acids
1,2,3-trichlorobenzene trichlorobenzene: commercial grade of trichlorobenzene containing 70% 1,2,4-trichlorobenzene & 30% 1,2,3-trichlorobenzene; see also record for 1,2,4-trichlorobenzene. trichlorobenzene : Any member of the class of chlorobenzenes carrying three chloro substituents at unspecified positions.. 1,2,3-trichlorobenzene : A trichlorobenzene carrying chloro substituents at positions 1, 2 and 3.	2.04	1	0	trichlorobenzene
hexamethylbenzene hexamethylbenzene : A methylbenzene that is benzene in which all six hydrogens have been replaced by methyl groups.	2.48	2	0	methylbenzene
xylitol xylooligosaccharide: structure in first source. pentitol : An alditol obtained by reduction of any pentose.. xylooligosaccharide : An oligosaccharide comprised of xylose residues.	2.01	1	0
2,4,6-trichlorophenol [no description available]	2.31	1	0	trichlorophenol	carcinogenic agent
2,3,5-triiodobenzoic acid 2,3,5-triiodobenzoic acid: inhibitor of auxin transport; RN given refers to parent cpd. 2,3,5-triiodobenzoic acid : A member of the class of benzoic acids that is benzoic acid in which the hydrogens at positions 2, 3 and 5 are replaced by iodine atoms. It is an auxin polar transport inhibitor.	2.5	2	0	benzoic acids; organoiodine compound	antiauxins
pyromellitic dianhydride [no description available]	2.07	1	0
thymol Thymol: A phenol obtained from thyme oil or other volatile oils used as a stabilizer in pharmaceutical preparations, and as an antiseptic (antibacterial or antifungal) agent.. thymol : A phenol that is a natural monoterpene derivative of cymene.	4.35	4	1	monoterpenoid; phenols	volatile oil component
salicylaldehyde o-hydroxybenzaldehyde: structure in first source	2.02	1	0	hydroxybenzaldehyde	nematicide; plant metabolite
1-methylnaphthalene 1-methylnaphthalene : A methylnaphthalene carrying a methyl substituent at position 1.	2.04	1	0	methylnaphthalene	carcinogenic agent; plant metabolite
1-chloronaphthalene 1-chloronaphthalene: word preservative; in xylamon the active ingredient is 60% 1-chloronaphthalene; structure in Merck Index, 9th ed, #2126	2.04	1	0
xanthone xanthone : The parent compound of the xanthone class consisting of xanthene bearing a single oxo substituent at position 9.	2.93	4	0	xanthones	insecticide
decalin decalin: RN given refers to cpd without isomeric designation; don't confuse with decaline which has a nitrogen at the juncture of the two rings;. trans-decalin : The trans-stereoisomer of decalin.. decalin : An ortho-fused bicyclic hydrocarbon that is the decahydro- derivative of naphthalene.	3.01	4	0	ortho-fused bicyclic hydrocarbon	solvent
quinoxalines quinoxaline : A naphthyridine in which the nitrogens are at positions 1 and 4.	6.28	11	1	mancude organic heterobicyclic parent; naphthyridine; ortho-fused heteroarene
quinoline [no description available]	2.25	1	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinolines
2-methylnaphthalene 2-methylnaphthalene: RN given refers to parent cpd. 2-methylnaphthalene : A methylnaphthalene carrying a methyl substituent at position 2.	2.04	1	0	methylnaphthalene
2-chloronaphthalene 2-chloronaphthalene: structure in first source	2.04	1	0
3,3'-diaminobenzidine 3,3'-Diaminobenzidine: A chemically and thermodynamically stable derivative of BENZIDINE.. 3,3'-diaminobenzidine : A member of the class of biphenyls that is benzidine in which one of the hydrogens ortho to each of the amino groups has been replaced by an amino group.	2.01	1	0	biphenyls; substituted aniline	histological dye
naphthacene tetracene : An acene that consists of four ortho-fused benzene rings in a rectilinear arrangement.	2.74	3	0	acene; tetracenes
tolonium chloride Tolonium Chloride: A phenothiazine that has been used as a hemostatic, a biological stain, and a dye for wool and silk. Tolonium chloride has also been used as a diagnostic aid for oral and gastric neoplasms and in the identification of the parathyroid gland in thyroid surgery.. tolonium chloride : An organic chloride salt having 3-amino-7-(dimethylamino)-2-methylphenothiazin-5-ium (tolonium) as the counterion. It is a blue nuclear counterstain that can be used to demonstrate Nissl substance and is also useful for staining mast cell granules, both in metachromatic and orthochromatic techniques.	1.99	1	0
phenidone phenidone: photographic developer; RN given refers to parent cpd; structure	3.77	10	0
diphenyl diphenyl: RN given refers to unlabeled cpd; structure	2.04	1	0	aromatic fungicide; benzenes; biphenyls	antifungal agrochemical; antimicrobial food preservative
xanthenes Xanthenes: Compounds with three aromatic rings in linear arrangement with an OXYGEN in the center ring.	4.69	9	0	xanthene
methyleugenol methyleugenol: structure	2.49	2	0	phenylpropanoid
1-phenylpropanol 1-phenylpropanol: structure in first source	5.23	14	0	organic molecular entity
methyl benzoate methyl benzoate : A benzoate ester obtained by condensation of benzoic acid and methanol.	2.48	2	0	benzoate ester; methyl ester	insect attractant; metabolite
synephrine [no description available]	1.94	1	0	ethanolamines; phenethylamine alkaloid; phenols	alpha-adrenergic agonist; plant metabolite
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)	2.48	2	0	benzoate ester; paraben; phenols	antifungal agent; antimicrobial agent
indene indene: structure in first source. 1H-indene : An ortho-fused bicyclic arene comprising of benzene and cyclopentene rings.	2.91	4	0	indene; ortho-fused bicyclic arene
benzotriazole benzotriazole: inhibitor of atmospheric metal corrosion; also component of motion picture film & Neva brake fluid. benzotriazole : The simplest member of the class of benzotriazoles that consists of a benzene nucleus fused to a 1H-1,2,3-triazole ring.	2.02	1	0	benzotriazoles	environmental contaminant; xenobiotic
benzothiophene [no description available]	2.78	3	0	1-benzothiophenes; benzothiophene
2-xylene 2-xylene: RN given refers to parent cpd. o-xylene : A xylene substituted by methyl groups at positions 1 and 2.	2.04	1	0	xylene
2-chlorotoluene 2-chlorotoluene: RN given refers to parent cpd	2.04	1	0
2-dichlorobenzene 2-dichlorobenzene: structure. 1,2-dichlorobenzene : A dichlorobenzene carrying chloro substituents at positions 1 and 2.	2.04	1	0	dichlorobenzene	hepatotoxic agent; metabolite
2-toluidine 2-toluidine: RN given refers to parent cpd. o-toluidine : An aminotoluene in which the amino substituent is ortho to the methyl group.	2.97	1	0	aminotoluene	carcinogenic agent
pseudocumene 1,2,4-trimethylbenzene : A trimethylbenzene carrying methyl groups at positions 1, 2 and 4.	2.04	1	0	trimethylbenzene	neurotoxin
durene durene: structure. durene : A tetramethylbenzene carrying methyl groups at positions 1, 2, 4 and 5.	2.04	1	0	tetramethylbenzene
1,2,4,5-tetrachlorobenzene 1,2,4,5-tetrachlorobenzene : A tetrachlorobenzene carrying chloro groups at positions 1, 2, 4 and 5.	2.04	1	0	tetrachlorobenzene
3-methylpentane 3-methylpentane : An alkane that is pentane which is substituted by a methyl group at position 3. It is used as a solvent in organic synthesis, as a lubricant and as a raw material for producing carbon black.	2.11	1	0	alkane; volatile organic compound	allelochemical; human metabolite; non-polar solvent
methyl acrylate [no description available]	2.05	1	0	enoate ester
methylcyclopentane methylcyclopentane: toxic; RN 96-37-7. methylcyclopentane : A cycloalkane that is cyclopentane substituted by a single methyl group.	3.03	4	0	cycloalkane; volatile organic compound	human metabolite; plant metabolite
cyclopentanol [no description available]	6.6	27	0	cyclopentanols
2-methyltetrahydrofuran 2-methyltetrahydrofuran: structure in first source	2.08	1	0
4-butyrolactone 4-Butyrolactone: One of the FURANS with a carbonyl thereby forming a cyclic lactone. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent.. tetrahydrofuranone : Any oxolane having an oxo- substituent at any position on the tetrahydrofuran ring.. gamma-butyrolactone : A butan-4-olide that is tetrahydrofuran substituted by an oxo group at position 2.	5.36	17	0	butan-4-olide	metabolite; neurotoxin
soman Soman: An organophosphorus compound that inhibits cholinesterase. It causes seizures and has been used as a chemical warfare agent.	5.14	10	1	phosphonic ester
1,3-ditolylguanidine 1,3-ditolylguanidine: structure given in first source; a selective ligand for the sigma binding sites in the brain	2.92	4	0	toluenes
tetrahydrofurfuryl alcohol tetrahydrofurfuryl alcohol: RN given refers to parent cpd; structure. tetrahydrofurfuryl alcohol : A primary alcohol that is methanol in which one of the hydrogens of the methyl group has been replaced by a tetrahydrofuran-2-yl group.	2.08	1	0	oxolanes; primary alcohol	protic solvent
furfuryl alcohol furfuryl alcohol: structure. furfuryl alcohol : A furan bearing a hydroxymethyl substituent at the 2-position.	3.88	3	0	furans; primary alcohol	Maillard reaction product
furaldehyde Furaldehyde: A heterocyclic compound consisting of a furan where the hydrogen at position 2 is substituted by a formyl group.. furfural : An aldehyde that is furan with the hydrogen at position 2 substituted by a formyl group.	3.77	10	0	aldehyde; furans	Maillard reaction product; metabolite
tert-butylbenzene [no description available]	2.04	1	0
pyrrolidonecarboxylic acid Pyrrolidonecarboxylic Acid: A cyclized derivative of L-GLUTAMIC ACID. Elevated blood levels may be associated with problems of GLUTAMINE or GLUTATHIONE metabolism.. 5-oxo-L-proline : An optically active form of 5-oxoproline having L-configuration.	1.94	1	0	5-oxoproline; L-proline derivative; non-proteinogenic L-alpha-amino acid	algal metabolite
cumene cumene : An alkylbenzene that is benzene carrying an isopropyl group.	2.04	1	0	alkylbenzene
methylphenyl carbinol 1-phenylethanol : An aromatic alcohol that is ethanol substituted by a phenyl group at position 1.. methylbenzyl alcohol : Members of the class of benzyl alcohols substituted by at least one methyl group.	2.01	1	0	aromatic alcohol	mouse metabolite
acetophenone acetophenone : A methyl ketone that is acetone in which one of the methyl groups has been replaced by a phenyl group.	2.17	1	0	acetophenones	animal metabolite; photosensitizing agent; xenobiotic
nitrobenzene nitrobenzene : A nitroarene consisting of benzene carrying a single nitro substituent. An industrial chemical used widely in the production of aniline.	2.07	1	0	nitroarene; nitrobenzenes
trehalose alpha,alpha-trehalose : A trehalose in which both glucose residues have alpha-configuration at the anomeric carbon.	3.13	4	0	trehalose	Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
sym-trinitrobenzene Trinitrobenzenes: Benzene derivatives which are substituted with three nitro groups in any position.. 1,3,5-trinitrobenzene : A trinitrobenzene in which each of the nitro groups is meta- to the other two.	1.97	1	0	trinitrobenzene	explosive
carvone carvone: an oxidized derivative of limonene; RN given refers to cpd without isomeric designation; L-carvone has spearmint flavor, D-carvone has dill/caraway flavor. carvone : A p-menthane monoterpenoid that consists of cyclohex-2-enone having methyl and isopropenyl substituents at positions 2 and 5, respectively.	3.17	5	0	botanical anti-fungal agent; carvones	allergen
4-bromophenacyl bromide 4-bromophenacyl bromide: phospholipidase A(2) inhibitor; structure	1.97	1	0
gamma-terpinene gamma-terpinene: RN given refers to gamma-terpinene; structure. gamma-terpinene : One of three isomeric monoterpenes differing in the positions of their two double bonds (alpha- and beta-terpinene being the others). In gamma-terpinene the double bonds are at the 1- and 4-positions of the p-menthane skeleton.	2.13	1	0	cyclohexadiene; monoterpene	antioxidant; human xenobiotic metabolite; plant metabolite; volatile oil component
4-cymene 4-cymene: structure. p-cymene : A monoterpene that is toluene substituted by an isopropyl group at position 4.	2.48	2	0	monoterpene; toluenes	human urinary metabolite; plant metabolite; volatile oil component
terephthalic acid terephthalic acid: RN given refers to 1,4-benzenedicarboxylic acid. terephthalic acid : A benzenedicarboxylic acid carrying carboxy groups at positions 1 and 4. One of three possible isomers of benzenedicarboxylic acid, the others being phthalic and isophthalic acids.	2.25	1	0	benzenedicarboxylic acid
ethylbenzene [no description available]	2.41	2	0	alkylbenzene
styrene Styrene: A colorless, toxic liquid with a strong aromatic odor. It is used to make rubbers, polymers and copolymers, and polystyrene plastics.. styrene : A vinylarene that is benzene carrying a vinyl group. It has been isolated from the benzoin resin produced by Styrax species.	2.8	3	0	styrenes; vinylarene; volatile organic compound	mouse metabolite; mutagen; plant metabolite
phenylhydrazine [no description available]	2.17	1	0	phenylhydrazines	xenobiotic
quinuclidines Quinuclidines: A class of organic compounds which contain two rings that share a pair of bridgehead carbon atoms and contains an amine group.	6.19	10	0	quinuclidines; saturated organic heterobicyclic parent
cyclamic acid Cyclamates: Salts and esters of cyclamic acid.. cyclohexylsulfamic acid : A member of the class of sulfamic acids that is sulfamic acid carrying an N-cyclohexyl substituent.	2.35	2	0	sulfamic acids	environmental contaminant; human xenobiotic 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.	2.42	2	0	pyridinium salt
cyclopentamine cyclopentamine: structure	2.63	3	0	secondary amino compound
1,3-cyclopentadiene 1,3-cyclopentadiene: structure	4.9	11	0	cycloalkadiene
boric acid [no description available]	2.05	1	0	boric acids	astringent
1,2-dihydrostilbene 1,2-dihydrostilbene: intermdiate in biosynthesis of dihydrophenanthrenes from phenylalanine. 1,2-dihydrostilbene : A diphenylethane that is the 1,2-dihydro derivative of stilbene.	2.04	1	0	diphenylethane
n-propylbenzene n-propylbenzene: RN given refers to parent cpd. propylbenzene : An alkylbenzene that is benzene having one of its aromatic hydrogens substituted by a propyl group.	2.04	1	0	alkylbenzene
n-butylbenzene butylbenzene : An alkylbenzene that is benzene substituted by a butyl group at position 1.	2.04	1	0	alkylbenzene
ethyl bromoacetate [no description available]	4.9	1	1
diethyl malonate diethyl malonate: isomer of diethylmalonic acid; one of most used compounds in drug synthesis, don't confuse with ethylmalonic acid	2.03	1	0	dicarboxylic acid
caprolactam Caprolactam: Cyclic amide of caproic acid used in manufacture of synthetic fibers of the polyamide type. Can cause local irritation.. epsilon-caprolactam : A member of the class of caprolactams that is azepane substituted by an oxo group at position 2.	2.04	1	0	caprolactams	human blood serum metabolite
1,4-dibromobenzene [no description available]	2.04	1	0	dibromobenzene
4-xylene p-xylene : A xylene with methyl groups at positions 1 and 4.	2.41	2	0	xylene
4-chlorotoluene 4-chlorotoluene: RN given refers to unlabeled cpd	2.04	1	0	monochlorobenzenes
ethylene dibromide Ethylene Dibromide: An effective soil fumigant, insecticide, and nematocide. In humans, it causes severe burning of skin and irritation of the eyes and respiratory tract. Prolonged inhalation may cause liver necrosis. It is also used in gasoline. Members of this group have caused liver and lung cancers in rodents. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), 1,2-dibromoethane may reasonably be anticipated to be a carcinogen.. 1,2-dibromoethane : A bromoalkane that is ethane carrying bromo substituents at positions 1 and 2. It is produced by marine algae.	2.04	1	0	bromoalkane; bromohydrocarbon	algal metabolite; carcinogenic agent; fumigant; marine metabolite; mouse metabolite; mutagen
butane butane : A straight chain alkane composed of 4 carbon atoms.	2.04	1	0	alkane; gas molecular entity	food propellant; refrigerant
1-butene but-1-ene : A butene with unsaturation at position 1.	2.04	1	0	butene
1,3-butadiene buta-1,3-diene : A butadiene with unsaturation at positions 1 and 3.	2.5	2	0	butadiene	carcinogenic agent; mutagen
acrolein [no description available]	3.66	9	0	enal	herbicide; human xenobiotic metabolite; toxin
allyl chloride [no description available]	2.04	1	0	organochlorine compound
2-bromoethylamine [no description available]	2.47	2	0
acrylonitrile [no description available]	2.47	2	0	aliphatic nitrile; volatile organic compound	antifungal agent; carcinogenic agent; fungal metabolite; mutagen; polar aprotic solvent
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.	2.49	2	0	primary allylic alcohol; propenol	antibacterial agent; fungicide; herbicide; insecticide; plant metabolite
propargyl alcohol propargyl alcohol: irreversibly inactivates alcohol oxidase; RN given refers to parent cpd. prop-2-yn-1-ol : A terminal acetylenic compound that is prop-2-yne substituted by a hydroxy group at position 1.	2.04	1	0	propynol; terminal acetylenic compound; volatile organic compound	antifungal agent; Saccharomyces cerevisiae metabolite
glyoxal [no description available]	1.95	1	0	dialdehyde	agrochemical; allergen; pesticide; plant growth regulator
sarin Sarin: An organophosphorus ester compound that produces potent and irreversible inhibition of cholinesterase. It is toxic to the nervous system and is a chemical warfare agent.. isopropyl methylphosphonofluoridate : A phosphinic ester that is the isopropyl ester of methylphosphonofluoridic acid.. sarin : A racemate composed of equal amounts of (R)- and (S)-sarin. A potent and irreversible inhibitor of acetylcholinesterase that is toxic to the nervous system and is employed as a chemical warfare agent.	2.92	4	0	fluorine molecular entity; phosphinic ester
2-methylpentane Hexanes: Six-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Various polyneuropathies are caused by hexane poisoning.	3.47	7	0	alkane
isoamylamine isoamylamine: RN given refers to parent cpd. isopentylamine : A primary aliphatic amine that is butan-1-amine carrying a methyl substituent at position 3.	2.31	1	0	primary aliphatic amine	bacterial metabolite; plant metabolite
3-hydroxybutanal [no description available]	3.79	10	0
diisopropylamine diisopropylamine: structure given in first source	2.03	1	0
acetic anhydride acetic anhydride: RN given refers to unlabeled cpd; structure. acetic anhydride : An acyclic carboxylic anhydride derived from acetic acid.	2.07	1	0	acyclic carboxylic anhydride	metabolite; reagent
maleic anhydride Maleic Anhydrides: Used in copolymerization reactions, in the Diels-Alder(diene)synthesis, in the preparation of resins, pharmaceuticals and agricultural chemicals. It is a powerful irritant and causes burns.. maleic anhydride : A cyclic dicarboxylic anhydride that is the cyclic anhydride of maleic acid.	2.75	3	0	cyclic dicarboxylic anhydride; furans	allergen
3-xylene m-xylene : A xylene carrying methyl groups at positions 1 and 3.	2.04	1	0	xylene
methyl malonate methyl malonate: do not confuse with methylmalonate, i.e., malonic acid substituted with a methyl group on C2; structure	2.03	1	0
mesitylene mesitylene: structure. 1,3,5-trimethylbenzene : A trimethylbenzene carrying methyl substituents at positions 1, 3 and 5.	2.04	1	0	trimethylbenzene
1,3,5-trichlorobenzene 1,3,5-trichlorobenzene: structure in first source. 1,3,5-trichlorobenzene : A trichlorobenzene carrying chloro substituents at positions 1, 3 and 5.	2.04	1	0	trichlorobenzene
cyanuric acid cyanuric acid: RN given refers to parent cpd. isocyanuric acid : The keto tautomer of cyanuric acid.. cyanuric acid : The enol tautomer of isocyanuric acid.	2.01	1	0	1,3,5-triazinanes; 1,3,5-triazines; heteroaryl hydroxy compound	xenobiotic
bromobenzene [no description available]	2.04	1	0	bromoarene; bromobenzenes; volatile organic compound	hepatotoxic agent; mouse metabolite; non-polar solvent
methylcyclohexane methylcyclohexane: structure in first source. methylcyclohexane : A cycloalkane that is cyclohexane substituted by a single methyl group.	2.1	1	0	cycloalkane; volatile organic compound	aprotic solvent; human metabolite; plant metabolite
4-methylpyridine 4-methylpyridine: structure in first source. 4-methylpyridine : A methylpyridine in which the methyl substituent is at position 4.	2.06	1	0	methylpyridine
chlorobenzene [no description available]	2.04	1	0	monochlorobenzenes	solvent
cyclohexanol Cyclohexanols: Monohydroxy derivatives of cyclohexanes that contain the general formula R-C6H11O. They have a camphorlike odor and are used in making soaps, insecticides, germicides, dry cleaning, and plasticizers.. cyclohexanols : An alcohol in which one or more hydroxy groups are attached to a cyclohexane skeleton.	3.78	11	0	cyclohexanols; secondary alcohol	solvent
cyclohexanone [no description available]	3.53	8	0	cyclohexanones	human xenobiotic metabolite
2-picoline 2-picoline: structure in first source. 2-methylpyridine : A methylpyridine carrying a methyl substituent at position 2.	2.05	1	0	methylpyridine
pentane Pentanes: Five-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives.. pentane : A straight chain alkane consisting of 5 carbon atoms.	4.04	14	0	alkane; volatile organic compound	non-polar solvent; refrigerant
1-pentene 1-pentene: structure in first source	2.04	1	0
butyl chloride butyl chloride: structure	2.04	1	0
vinyl ether vinyl ether: major descriptor (65-85); on-line search VINYL COMPOUNDS (66-85); Index Medicus search VINYL ETHER (65-85)	2.92	4	0	ether
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.	13.37	58	1	pyrrole; secondary amine
tetrahydrofuran oxolane : A cyclic ether that is butane in which one hydrogen from each methyl group is substituted by an oxygen.	8.42	7	0	cyclic ether; oxolanes; saturated organic heteromonocyclic parent; volatile organic compound	polar aprotic solvent
furan furan : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing four carbons and one oxygen, with formula C4H4O. It is a toxic, flammable, low-boiling (31degreeC) colourless liquid.	3.68	9	0	furans; mancude organic heteromonocyclic parent; monocyclic heteroarene	carcinogenic agent; hepatotoxic agent; Maillard reaction product
thiophenes Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.	5.08	41	0	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
2,5-hexanedione 2,5-hexanedione: metabolite of methyl-n-butyl ketone. 2,5-hexanedione : A diketone that is hexane substituted by oxo groups at positions 2 and 5. It is a toxic metabolite of hexane and of 2-hexanone	1.98	1	0	diketone; methyl ketone	human xenobiotic metabolite; neurotoxin
n-hexane hexane : An unbranched alkane containing six carbon atoms.	2.77	3	0	alkane; volatile organic compound	neurotoxin; non-polar solvent
cyclohexane Cyclohexane: C6H12. cyclohexane : An alicyclic hydrocarbon comprising a ring of six carbon atoms; the cyclic form of hexane, used as a raw material in the manufacture of nylon.	4.97	12	0	cycloalkane; volatile organic compound	non-polar solvent
cyclohexene cyclohexene : A cycloalkene that is cylohexane with a single double bond.	4.79	10	0	cycloalkene
piperidine [no description available]	2.46	2	0	azacycloalkane; piperidines; saturated organic heteromonocyclic parent; secondary amine	base; catalyst; human metabolite; non-polar solvent; plant metabolite; protic solvent; reagent
2-octanone 2-octanone : A methyl ketone that is octane substituted by an oxo group at position 2.	2.01	1	0	methyl ketone	metabolite
1-hexanol 1-hexanol: RN given refers to parent cpd. hexanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of six carbon atoms.. hexan-1-ol : A primary alcohol that is hexane substituted by a hydroxy group at position 1.	3.69	9	0	hexanol; primary alcohol	alarm pheromone; antibacterial agent; fragrance; plant metabolite
hexahydroazepine hexahydroazepine: RN given refers to parent cpd. azepane : An azacycloalkane that is cycloheptane in which one of the carbon atoms is replaced by a nitrogen atom.	1.99	1	0	azacycloalkane; azepanes; saturated organic heteromonocyclic parent
heptanol Heptanol: A colorless liquid with a fragrant odor. It is used as an intermediate, solvent and in cosmetics.. heptanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of seven carbon atoms.. heptan-1-ol : A primary alcohol that is heptane substituted by a hydroxy group at position 1. It has been isolated from Capillipedium parviflorum.	2.41	1	0	heptanol; primary alcohol	flavouring agent; fragrance; gap junctional intercellular communication inhibitor; plant metabolite
nonane iotrochotin: toxin from the Caribbean sponge Iotrochota birotulata, which selectively permeabilizes synaptosomes. nonane : A straight chain alkane composed of 9 carbon atoms.	2.43	2	0	alkane	plant metabolite; volatile oil component
pelargonic acid pelargonic acid: K salt acts as cariostatic agent; RN given refers to parent cpd; structure. nonanoic acid : A C9 straight-chain saturated fatty acid which occurs naturally as esters of the oil of pelargonium. Has antifungal properties, and is also used as a herbicide as well as in the preparation of plasticisers and lacquers.	2.02	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; antifeedant; Daphnia magna metabolite; plant metabolite
obidoxime chloride Obidoxime Chloride: Cholinesterase reactivator occurring in two interchangeable isomeric forms, syn and anti.	1.95	1	0
propylene propylene: structure	3.12	5	0	alkene; gas molecular entity	refrigerant; xenobiotic
3-hydroxy-3-methylbutene 3-hydroxy-3-methylbutene: narcotic, sleep-producing principle from hops; RN given refers to parent cpd. 3-hydroxy-3-methylbut-1-ene : A tertiary alcohol that is 3-methylbut-1-ene carrying a hydroxy substituent at position 3.	2.11	1	0	olefinic compound; tertiary alcohol	animal metabolite; fragrance; pheromone; plant metabolite
acetol hydroxyacetone : A propanone that is acetone in which one of the methyl hydrogens is replaced by a hydroxy group.	2.42	2	0	methyl ketone; primary alcohol; primary alpha-hydroxy ketone; propanones	Escherichia coli metabolite; human metabolite; mouse metabolite
maltol maltol: found in bark of young larch trees; isolated from Passiflora incarnata; possesses depressant properties in mice; potentiates hexobarbital-induced narcosis & inhibits spontaneous motor activity; structure	1.96	1	0	4-pyranones	metabolite
hexachlorobenzene Hexachlorobenzene: An agricultural fungicide and seed treatment agent.. hexachlorobenzene : A member of the class of chlorobenzenes that is benzene in which all of the hydrogens are replaced by chlorines. An agricultural fungicide introduced in the mid-1940s and formerly used as a seed treatment, its use has been banned since 1984 under the Stockholm Convention on Persistent Organic Pollutants.	2.04	1	0	aromatic fungicide; chlorobenzenes	antifungal agrochemical; carcinogenic agent; persistent organic pollutant
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.	2.39	2	0	aminoglycoside	allergen; antibacterial drug; Escherichia coli metabolite
benzoin [no description available]	2.03	1	0	benzoins; secondary alpha-hydroxy ketone	EC 3.1.1.1 (carboxylesterase) inhibitor
isoquinoline [no description available]	2.42	2	0	azaarene; isoquinolines; mancude organic heterobicyclic parent; ortho-fused heteroarene
anthracene acene : A polycyclic aromatic hydrocarbon consisting of fused benzene rings in a rectilinear arrangement.. acenes : Polycyclic aromatic hydrocarbons consisting of fused benzene rings in a rectilinear arrangement and their substitution derivatives.	2.48	2	0	acene; anthracenes; ortho-fused tricyclic hydrocarbon
veratraldehyde [no description available]	2.02	1	0	benzaldehydes; dimethoxybenzene	antifungal agent
dibenzoylmethane dibenzoylmethane : A beta-diketone that is acetylacetone (acac) in which both methyl groups have been replaced by phenyl groups. It is a minor constituent of the root extract of licorice (Glycyrrhiza glabra) and exhibits antimutagenic and anticancer effects.	2.07	1	0	aromatic ketone; beta-diketone	antimutagen; antineoplastic agent; metabolite
cyclopentanone [no description available]	13.49	140	0	cyclopentanones	Maillard reaction product
ethylene urea ethylene urea: used in manufacture of polymers, finishing agents for textiles & leather, in formulation of plasticizers, lacquers & adhesives; structure. imidazolidinone : An imidazolidine containing one or more oxo groups.	2.21	1	0	imidazolidinone; ureas
ethyl vanillin ethyl vanillin : A member of the class of benzaldehydes that is vanillin in which the methoxy group is replaced by an ethoxy group.	2.44	2	0	aromatic ether; benzaldehydes; phenols	antioxidant; flavouring agent
triethylamine [no description available]	2.05	1	0	tertiary amine
2,5-norbornadiene [no description available]	2.01	1	0
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.	2.13	1	0	anthrapyrazole; aromatic ketone; cyclic ketone	antineoplastic agent; c-Jun N-terminal kinase inhibitor; geroprotector
1,4-naphthoquinone naphthoquinone : A polycyclic aromatic ketone metabolite of naphthalene.. 1,4-naphthoquinone : The parent structure of the family of 1,4-naphthoquinones, in which the oxo groups of the quinone moiety are at positions 1 and 4 of the naphthalene ring. Derivatives have pharmacological properties.	2.46	2	0	1,4-naphthoquinones
alpha-naphthylphthalamic acid alpha-naphthylphthalamic acid: RN given refers to parent cpd; structure. naptalam : A dicarboxylic acid monoamide which results from addition of one equivalent of 1-naphthylamine to phthalic anhydride.	2.97	4	0	carboxylic acid; dicarboxylic acid monoamide; N-(1-naphthyl)carboxamide	herbicide
indolebutyric acid indolebutyric acid: RN given refers to parent cpd. indole-3-butyric acid : A indol-3-yl carboxylic acid that is butanoic acid carrying a 1H-indol-3-yl substituent at position 1.	3.47	7	0	indol-3-yl carboxylic acid	auxin; plant hormone; plant 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.	5.66	5	1	naphthol	antinematodal drug; genotoxin; human urinary metabolite; human xenobiotic metabolite; mouse metabolite; radical scavenger
shikimic acid Shikimic Acid: A tri-hydroxy cyclohexene carboxylic acid important in biosynthesis of so many compounds that the shikimate pathway is named after it.. shikimic acid : A cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid substituted by hydroxy groups at positions 3, 4 and 5 (the 3R,4S,5R stereoisomer). It is an intermediate metabolite in plants and microorganisms.	3.18	5	0	alpha,beta-unsaturated monocarboxylic acid; cyclohexenecarboxylic acid; hydroxy monocarboxylic acid	Escherichia coli metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
benzyl cyanide benzyl cyanide: reversible monoamine oxidase inhibitor	2.78	3	0	benzenes; nitrile	animal metabolite; pheromone
estragole estragole : A phenylpropanoid that is chavicol in which the hydroxy group is replaced by a methoxy group.	2.05	1	0	alkenylbenzene; monomethoxybenzene; phenylpropanoid	carcinogenic agent; flavouring agent; genotoxin; insect attractant; plant metabolite
citronellol citronellol: alcohol form of citronellal; found in rose oil; RN given refers to parent cpd without isomeric designation; structure. citronellol : A monoterpenoid that is oct-6-ene substituted by a hydroxy group at position 1 and methyl groups at positions 3 and 7.. insect repellent : An insecticide that acts as a repellent to insects.	4.9	1	1	monoterpenoid	plant metabolite
ethyl acetate ethyl acetate : The acetate ester formed between acetic acid and ethanol.	3.36	6	0	acetate ester; ethyl ester; volatile organic compound	EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor; metabolite; polar aprotic solvent; Saccharomyces cerevisiae metabolite
2-hydroxypyridine hydroxypyridine : Any member of the class of pyridines with at least one hydroxy substituent.. pyridin-2-ol : A monohydroxypyridine that is pyridine substituted by a hydroxy group at position 2.	2	1	0	monohydroxypyridine	plant metabolite
hexanoic acid hexanoic acid : A C6, straight-chain saturated fatty acid.	3	4	0	medium-chain fatty acid; straight-chain saturated fatty acid	human metabolite; plant metabolite
n-heptane Heptanes: Seven-carbon alkanes with the formula C7H16.. heptane : A straight-chain alkane with seven carbon atoms. It has been found in Jeffrey pine (Pinus jeffreyi).	2.89	4	0	alkane; volatile organic compound	non-polar solvent; plant metabolite
hexadecylamine [no description available]	2.31	1	0	alkylamine
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.	2.69	3	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.	2.91	4	0	D-aldohexose derivative
diphenhydramine hydrochloride Antitussive Agents: Agents that suppress cough. They act centrally on the medullary cough center. EXPECTORANTS, also used in the treatment of cough, act locally.. diphenhydramine hydrochloride : The hydrochloride salt of diphenhydramine.	8.79	36	1	hydrochloride; organoammonium salt	anti-allergic agent; antiemetic; antiparkinson drug; antipruritic drug; H1-receptor antagonist; local anaesthetic; muscarinic antagonist; sedative
ditiocarb Ditiocarb: A chelating agent that has been used to mobilize toxic metals from the tissues of humans and experimental animals. It is the main metabolite of DISULFIRAM.. diethyldithiocarbamic acid : A member of the class of dithiocarbamic acids that is diethylcarbamic acid in which both of the oxygens are replaced by sulfur.	2.74	3	0	dithiocarbamic acids	chelator; copper chelator
potassium cyanide [no description available]	5.22	3	1	cyanide salt; one-carbon compound; potassium salt	EC 1.15.1.1 (superoxide dismutase) inhibitor; EC 1.9.3.1 (cytochrome c oxidase) inhibitor; neurotoxin
aziridine [no description available]	2.8	3	0	azacycloalkane; aziridines; saturated organic heteromonocyclic parent	alkylating agent
quinestrol Quinestrol: The 3-cyclopentyl ether of ETHINYL ESTRADIOL. After gastrointestinal absorption, it is stored in ADIPOSE TISSUE, slowly released, and metabolized principally to the parent compound. It has been used in ESTROGEN REPLACEMENT THERAPY. (From AMA Drug Evaluations Annual, 1992, p1011)	3.33	1	1	17-hydroxy steroid; terminal acetylenic compound	xenoestrogen
catechin Catechin: An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.. catechin : Members of the class of hydroxyflavan that have a flavan-3-ol skeleton and its substituted derivatives.. rac-catechin : A racemate comprising equimolar amounts of (+)- and (-)-catechin. (+)-catechin : The (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite.	3.6	8	0	catechin	antioxidant; plant metabolite
1,12-benzoperylene 1,12-benzoperylene: structure; see also record for benzoperylene	2.04	1	0	ortho- and peri-fused polycyclic arene
benzo(e)pyrene benzo(e)pyrene: RN given refers to parent cpd. benzo[e]pyrene : An ortho- and peri-fused polycyclic arene consisting of five fused benzene rings. It is listed as a Group 3 carcinogen by the IARC.	2.04	1	0	ortho- and peri-fused polycyclic arene	carcinogenic agent; mutagen
perylene Perylene: A 20-carbon dibenz(de,kl)anthracene that can be viewed as a naphthalene fused to a phenalene or as dinaphthalene. It is used as fluorescent lipid probe in the cytochemistry of membranes and is a polycyclic hydrocarbon pollutant in soil and water. Derivatives may be carcinogenic.. perylene : An ortho- and peri-fused polycyclic arene comprising of five benzene rings that is anthracene in which the d,e and k,l sides are fused to benzene rings.	4.23	5	0	ortho- and peri-fused polycyclic arene; perylenes
benzo(j)fluoranthene benzo(j)fluoranthene: dihydrodiol metabolites identified as mutagens; structure given in first source	2.04	1	0	naphthalenes
benzo(b)fluoranthene benzo[b]fluoranthene : An ortho- and peri-fused polycyclic arene that consists of a benzene ring fused with a acephenanthrylene ring.	2.04	1	0	ortho- and peri-fused polycyclic arene	mutagen
fluoranthene fluoranthene: structure. fluoranthene : An ortho- and peri-fused polycyclic arene consisting of a naphthalene and benzene unit connected by a five-membered ring.	2.44	2	0	ortho- and peri-fused polycyclic arene
benzo(k)fluoranthene [no description available]	2.04	1	0	naphthalenes
acenaphthylene acenaphthylene: RN given refers to parent cpd. acenaphthylene : A ortho- and peri-fused tricyclic hydrocarbon that occurs in coal tar.	3.58	2	0	acenaphthylenes; ortho- and peri-fused polycyclic arene; ortho- and peri-fused tricyclic hydrocarbon
triphenylene triphenylene: structure. triphenylene : An ortho-fused polycyclic arene consisting of four fused benzene rings.	2.04	1	0	ortho-fused polycyclic arene
chrysene chrysene: structure in Merck Index, 9th ed, #2252. chrysene : An ortho-fused polycyclic arene found commonly in the coal tar.	2.04	1	0	ortho-fused polycyclic arene	plant metabolite
dibenzo(aj)anthracene dibenzo(aj)anthracene: structure in first source	2.04	1	0	phenanthrenes
benzo(a)fluorene benzo(a)fluorene: structure in first source	2.04	1	0	carbotetracyclic compound
benzo(b)fluorene benzo(b)fluorene: structure in first source	2.04	1	0	carbotetracyclic compound
quinazolines Quinazolines: A group of aromatic heterocyclic compounds that contain a bicyclic structure with two fused six-membered aromatic rings, a benzene ring and a pyrimidine ring.. quinazoline : A mancude organic heterobicyclic parent that is naphthalene in which the carbon atoms at positions 1 and 3 have been replaced by nitrogen atoms.. quinazolines : Any organic heterobicyclic compound based on a quinazoline skeleton and its substituted derivatives.	3.41	7	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinazolines
acridines Acridines: Compounds that include the structure of acridine.. acridine : A polycyclic heteroarene that is anthracene in which one of the central CH groups is replaced by a nitrogen atom.	2.35	2	0	acridines; mancude organic heterotricyclic parent; polycyclic heteroarene	genotoxin
indazoles Indazoles: A group of heterocyclic aromatic organic compounds consisting of the fusion of BENZENE and PYRAZOLES.	3.8	3	0	indazole
benzofuran benzofuran: RN & structure given in first source. 1-benzofuran : A benzofuran consisting of fused benzene and furan rings. It is the parent compound of the class of 1-benzofurans.	3.56	2	0	1-benzofurans; benzofuran
benzoxazoles 1,3-benzoxazole : A benzoxazole in which the benzene ring is fused to a 1,3-oxazole ring across positions 4 and 5.. benzoxazole : Compounds based on a fused 1,2- or 1,3-oxazole and benzene bicyclic ring skeleton.	2.93	4	0	1,3-benzoxazoles; mancude organic heterobicyclic parent
azulene [no description available]	6.31	12	1	azulenes; mancude carbobicyclic parent; ortho-fused bicyclic arene	plant metabolite; volatile oil component
bicyclo(2.2.2)octane bicyclo(2.2.2)octane: structure in first source	3.25	1	0
triethylenediamine triethylenediamine: RN given refers to parent cpd. triethylenediamine : An organic heterobicylic compound that is piperazine with an ethane-1,2-diyl group forming a bridge between N1 and N4. It is typically used as a catalyst in polymerization reactions.	2.1	1	0	bridged compound; diamine; saturated organic heterobicyclic parent; tertiary amino compound	antioxidant; catalyst; reagent
adamantane Adamantane: A tricyclo bridged hydrocarbon.	4.55	7	0	adamantanes; polycyclic alkane
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.	6.53	8	1	isoxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
oxazoles Oxazoles: Five-membered heterocyclic ring structures containing an oxygen in the 1-position and a nitrogen in the 3-position, in distinction from ISOXAZOLES where they are at the 1,2 positions.. 1,3-oxazole : A five-membered monocyclic heteroarene that is an analogue of cyclopentadiene with O in place of CH2 at position 1 and N in place of CH at position 3.. oxazole : An azole based on a five-membered heterocyclic aromatic skeleton containing one N and one O atom.	3.87	12	0	1,3-oxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
thiazoles [no description available]	6.54	60	0	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
pyrimidine pyrimidine : The parent compound of the pyrimidines; a diazine having the two nitrogens at the 1- and 3-positions.	2.73	3	0	diazine; pyrimidines	Daphnia magna metabolite
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.	7.11	15	1	diazine; pyrazines	Daphnia magna metabolite
cyclooctane [no description available]	7.36	2	0
triphenyltetrazolium triphenyltetrazolium: RN given refers to parent cpd. 2,3,5-triphenyltetrazolium : An organic cation that is tetrazole carrying three phenyl substituents at positions 2, 3 and 5.	2.04	1	0	organic cation
ephedrine Ephedrine: A phenethylamine found in EPHEDRA SINICA. PSEUDOEPHEDRINE is an isomer. It is an alpha- and beta-adrenergic agonist that may also enhance release of norepinephrine. It has been used for asthma, heart failure, rhinitis, and urinary incontinence, and for its central nervous system stimulatory effects in the treatment of narcolepsy and depression. It has become less extensively used with the advent of more selective agonists.. (-)-ephedrine : A phenethylamine alkaloid that is 2-phenylethanamine substituted by a methyl group at the amino nitrogen and a methyl and a hydroxy group at position 2 and 1 respectively.	1.94	1	0	phenethylamine alkaloid; phenylethanolamines	bacterial metabolite; environmental contaminant; nasal decongestant; plant metabolite; sympathomimetic agent; vasoconstrictor agent; xenobiotic
muscarine Muscarine: A toxic alkaloid found in Amanita muscaria (fly fungus) and other fungi of the Inocybe species. It is the first parasympathomimetic substance ever studied and causes profound parasympathetic activation that may end in convulsions and death. The specific antidote is atropine.	2.65	3	0	monosaccharide
hydrazine diamine : Any polyamine that contains two amino groups.	3.85	12	0	azane; hydrazines	EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
thiocyanate thiocyanate: RN given refers to parent cpd. thiocyanate : A pseudohalide anion obtained by deprotonation of the thiol group of thiocyanic acid.	2.01	1	0	pseudohalide anion; sulfur molecular entity	human metabolite
benactyzine Benactyzine: A centrally acting muscarinic antagonist. Benactyzine has been used in the treatment of depression and is used in research to investigate the role of cholinergic systems on behavior.	2.89	4	0	diarylmethane
4-hydroxyphenyllactic acid 4-hydroxyphenyllactic acid: tyrosing metabolite; RN given refers to cpd without isomeric designation. 3-(4-hydroxyphenyl)lactic acid : A 2-hydroxy carboxylic acid that is lactic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group.	2.21	1	0	2-hydroxy carboxylic acid; phenols	bacterial metabolite; human metabolite
aminophylline Aminophylline: A drug combination that contains THEOPHYLLINE and ethylenediamine. It is more soluble in water than theophylline but has similar pharmacologic actions. It's most common use is in bronchial asthma, but it has been investigated for several other applications.. aminophylline : A mixture comprising of theophylline and ethylenediamine in a 2:1 ratio.	1.94	1	0	mixture	bronchodilator agent; cardiotonic drug
azacitidine Azacitidine: A pyrimidine analogue that inhibits DNA methyltransferase, impairing DNA methylation. It is also an antimetabolite of cytidine, incorporated primarily into RNA. Azacytidine has been used as an antineoplastic agent.. 5-azacytidine : An N-glycosyl-1,3,5-triazine that is 4-amino-1,3,5-triazin-2(1H)-one substituted by a beta-D-ribofuranosyl residue via an N-glycosidic linkage. An antineoplastic agent, it is used in the treatment of myeloid leukaemia.	7.74	8	4	N-glycosyl-1,3,5-triazine; nucleoside analogue	antineoplastic agent
diazomethane Diazomethane: A diazonium compound with the formula CH2N2.. diazomethane : The simplest diazo compound, in which a diazo group is attached to a methylene group.	4.35	6	0	diazo compound	alkylating agent; antineoplastic agent; carcinogenic agent; poison
diethyl sulfide ethyl sulfide : An aliphatic sulfide in which the sulfur atom is bonded to at least one ethyl group.. diethyl sulfide : An ethyl sulfide compound having two ethyl groups attached to a sulfur atom.	2.04	1	0	ethyl sulfide
galantamine Galantamine: A benzazepine derived from norbelladine. It is found in GALANTHUS and other AMARYLLIDACEAE. It is a cholinesterase inhibitor that has been used to reverse the muscular effects of GALLAMINE TRIETHIODIDE and TUBOCURARINE and has been studied as a treatment for ALZHEIMER DISEASE and other central nervous system disorders.. galanthamine : A benzazepine alkaloid isolated from certain species of daffodils.	2.45	2	0	benzazepine alkaloid fundamental parent; benzazepine alkaloid; organic heterotetracyclic compound; tertiary amino compound	antidote to curare poisoning; cholinergic drug; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; plant metabolite
methysergide Methysergide: An ergot derivative that is a congener of LYSERGIC ACID DIETHYLAMIDE. It antagonizes the effects of serotonin in blood vessels and gastrointestinal smooth muscle, but has few of the properties of other ergot alkaloids. Methysergide is used prophylactically in migraine and other vascular headaches and to antagonize serotonin in the carcinoid syndrome.. methysergide : A synthetic ergot alkaloid, structurally related to the oxytocic agent methylergonovine and to the potent hallucinogen LSD and used prophylactically to reduce the frequency and intensity of severe vascular headaches.	2.36	2	0	ergoline alkaloid
2-fluorophenol fluorophenol : A halophenol that is any phenol containing one or more covalently bonded fluorine atoms.	2.11	1	0
cuprizone [no description available]	2.21	1	0	organonitrogen compound; organooxygen compound
4-fluorophenol 4-fluorophenol: structure given in first source. 4-fluorophenol : A fluorophenol that is phenol in which the hydrogen para- to the hydroxy group has been replaced by a fluorine.	2.11	1	0	fluorophenol; monofluorobenzenes
citrulline citrulline : The parent compound of the citrulline class consisting of ornithine having a carbamoyl group at the N(5)-position.	1.98	1	0	amino acid zwitterion; citrulline	Daphnia magna metabolite; EC 1.14.13.39 (nitric oxide synthase) inhibitor; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; protective agent; Saccharomyces cerevisiae metabolite
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)	3.34	1	1	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
ethylene sulfide [no description available]	2.21	1	0	organosulfur heterocyclic compound; saturated organic heteromonocyclic parent
lithocholic acid Lithocholic Acid: A bile acid formed from chenodeoxycholate by bacterial action, usually conjugated with glycine or taurine. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as cholagogue and choleretic.. lithocholic acid : A monohydroxy-5beta-cholanic acid with a alpha-hydroxy substituent at position 3. It is a bile acid obtained from chenodeoxycholic acid by bacterial action.. lithocholate : A bile acid anion that is the conjugate base of lithocholic acid.	1.98	1	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.	3.45	2	0	17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; anabolic androgenic steroid	human metabolite
hydantoins Hydantoins: Compounds based on imidazolidine dione. Some derivatives are ANTICONVULSANTS.. imidazolidine-2,4-dione : An imidazolidinone with oxo groups at position 2 and 4.	3.79	3	0	imidazolidine-2,4-dione
chlorphentermine Chlorphentermine: A sympathomimetic agent that was formerly used as an anorectic. It has properties similar to those of DEXTROAMPHETAMINE. It has been implicated in lipid storage disorders and pulmonary hypertension. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1223)	1.94	1	0	amphetamines
fluorobenzenes Fluorobenzenes: Derivatives of BENZENE that contain FLUORINE.. monofluorobenzene : The simplest member of the class of monofluorobenzenes that is benzene carrying a single fluoro substituent.. fluorobenzenes : Any fluoroarene that is a benzene or a substituted benzene carrying at least one fluoro group.	2.41	2	0	monofluorobenzenes	NMR chemical shift reference compound
propadiene [no description available]	5.81	16	0	allenes
ketene ketene: structure. ketene : Carbonyl compounds where the C=O bond is conjugated to an alkylidene group.	3.28	6	0	ketene
hopane hopane: RN given refers to cpd without isomeric designation	7.45	2	0	terpenoid fundamental parent; triterpene
mesoxalic acid mesoxalic acid: structure	2.08	1	0	oxo dicarboxylic acid
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.	1.98	1	0	bile acid glycine conjugate	human metabolite
fusarium Fusarium: A mitosporic Hypocreales fungal genus, various species of which are important parasitic pathogens of plants and a variety of vertebrates. Teleomorphs include GIBBERELLA.	8.18	96	0
cholanthrene cholanthrene: structure given in first source	2.04	1	0
indirubin [no description available]	2.21	1	0
plumbagin plumbagin: a superoxide anion generator. plumbagin : A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 2 and 5 are substituted by methyl and hydroxy groups, respectively.	2.53	2	0	hydroxy-1,4-naphthoquinone; phenols	anticoagulant; antineoplastic agent; immunological adjuvant; metabolite
menadiol [no description available]	2.04	1	0	methylnaphthalenes; naphthalenediols; naphthohydroquinone
phosphoadenosine phosphosulfate Phosphoadenosine Phosphosulfate: 3'-Phosphoadenosine-5'-phosphosulfate. Key intermediate in the formation by living cells of sulfate esters of phenols, alcohols, steroids, sulfated polysaccharides, and simple esters, such as choline sulfate. It is formed from sulfate ion and ATP in a two-step process. This compound also is an important step in the process of sulfur fixation in plants and microorganisms.. 3'-phospho-5'-adenylyl sulfate : An adenosine bisphosphate having monophosphate groups at the 3'- and 5'-positions and a sulfo group attached to the phosphate at position 5'.	2.05	1	0	acyl sulfate; adenosine bisphosphate; purine ribonucleoside bisphosphate	Escherichia coli metabolite; mouse metabolite
emetine Emetine: The principal alkaloid of ipecac, from the ground roots of Uragoga (or Cephaelis) ipecacuanha or U. acuminata, of the Rubiaceae. It is used as an amebicide in many different preparations and may cause serious cardiac, hepatic, or renal damage and violent diarrhea and vomiting. Emetine inhibits protein synthesis in EUKARYOTIC CELLS but not PROKARYOTIC CELLS.. emetine : A pyridoisoquinoline comprising emetam having methoxy substituents at the 6'-, 7'-, 10- and 11-positions. It is an antiprotozoal agent and emetic. It inhibits SARS-CoV2, Zika and Ebola virus replication and displays antimalarial, antineoplastic and antiamoebic properties.	2.91	4	0	isoquinoline alkaloid; pyridoisoquinoline	antiamoebic agent; anticoronaviral agent; antiinfective agent; antimalarial; antineoplastic agent; antiprotozoal drug; antiviral agent; autophagy inhibitor; emetic; expectorant; plant metabolite; protein synthesis inhibitor
bicuculline Bicuculline: An isoquinoline alkaloid obtained from Dicentra cucullaria and other plants. It is a competitive antagonist for GABA-A receptors.. bicuculline : A benzylisoquinoline alkaloid that is 6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline which is substituted at the 5-pro-S position by a (6R)-8-oxo-6,8-dihydrofuro[3,4-e][1,3]benzodioxol-6-yl group. A light-sensitive competitive antagonist of GABAA receptors. It was originally identified in 1932 in plant alkaloid extracts and has been isolated from Dicentra cucullaria, Adlumia fungosa, Fumariaceae, and several Corydalis species.	4.2	5	0	benzylisoquinoline alkaloid; isoquinoline alkaloid; isoquinolines	agrochemical; central nervous system stimulant; GABA-gated chloride channel antagonist; GABAA receptor antagonist; neurotoxin
vasicinone vasicinone: isolated from Adhatoda vasica; structure given in first source	2.15	1	0
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.	2.71	3	0	dicarboxylic acid; L-proline derivative; non-proteinogenic L-alpha-amino acid; pyrrolidinecarboxylic acid	antinematodal drug; excitatory amino acid agonist
indole-3-carbaldehyde indole-3-carbaldehyde: metabolite of tryptophan; structure. indole-3-carbaldehyde : A heteroarenecarbaldehyde that is indole in which the hydrogen at position 3 has been replaced by a formyl group.	2.06	1	0	heteroarenecarbaldehyde; indole alkaloid; indoles	bacterial metabolite; human xenobiotic metabolite; marine metabolite; plant metabolite
phenylpropanolamine Phenylpropanolamine: A sympathomimetic that acts mainly by causing release of NOREPINEPHRINE but also has direct agonist activity at some adrenergic receptors. It is most commonly used as a nasal vasoconstrictor and an appetite depressant.. phenylpropanolamine : An amphetamine in which the parent 1-phenylpropan-2-amine skeleton is substituted at position 1 with an hydroxy group. A decongestant and appetite suppressant, it is commonly used in prescription and over-the-counter cough and cold preparations.. (-)-norephedrine : An amphetamine that is propylbenzene substituted by a hydroxy group at position 1 and by an amino group at position 2 (the 1R,2S-stereoisomer). It is a plant alkaloid.	2.34	2	0	amphetamines; phenethylamine alkaloid	plant metabolite
indoline indoline: structure given in first source	8.2	5	0	indoles
sodium carbonate sodium carbonate: used topically for dermatitides, mouthwash, vaginal douche; veterinary use as emergency emetic; RN given refers to carbonic acid, di-Na salt; structure	2.44	2	0	carbonate salt; organic sodium salt
butenolide butenolide: inhibits experimental allergic encephalomyelitis in rats. butenolide : A gamma-lactone that consists of a 2-furanone skeleton and its substituted derivatives.	3.01	4	0	butenolide
2-norbornene norbornene : A bridged compound that is cyclohexane with a methylene bridge between carbons 1 and 4 and a double bond at position 2.	3.06	1	0
carvacrol carvacrol : A phenol that is a natural monoterpene derivative of cymene. An inhibitor of bacterial growth, it is used as a food additive. Potent activator of the human ion channels transient receptor potential V3 (TRPV3) and A1 (TRPA1).	2.31	1	0	botanical anti-fungal agent; p-menthane monoterpenoid; phenols	agrochemical; antimicrobial agent; flavouring agent; TRPA1 channel agonist; volatile oil component
4-hydroxyphenylethanol 4-hydroxyphenylethanol: in chest gland secretion of galagos. 2-(4-hydroxyphenyl)ethanol : A phenol substituted at position 4 by a 2-hydroxyethyl group.	2.49	2	0	phenols	anti-arrhythmia drug; antioxidant; cardiovascular drug; fungal metabolite; geroprotector; plant metabolite; protective agent
cycloheptanone cycloheptanone: structure	3.1	5	0
cyclooctanone [no description available]	2.42	2	0
4-hydroxybutyric acid 4-hydroxybutyric acid: was an entry term to Sodium Oxybate (74-98). 4-hydroxybutyric acid : A 4-hydroxy monocarboxylic acid that is butyric acid in which one of the hydrogens at position 4 is replaced by a hydroxy group.	3.08	5	0	4-hydroxy monocarboxylic acid; hydroxybutyric acid	general anaesthetic; GHB receptor agonist; neurotoxin; sedative
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.	7.68	9	2
1,3-propanediol propane-1,3-diol : The simplest member of the class of propane-1,3-diols, consisting of propane in which one hydrogen from each methyl group is substituted by a hydroxy group. A colourless, viscous, water-miscible liquid with a high (210degreeC) boiling point, it is used in the synthesis of certain polymers and as a solvent and antifreeze.	2.4	2	0	propane-1,3-diols	metabolite; protic solvent
thiazolidines Thiazolidines: Reduced (protonated) form of THIAZOLES. They can be oxidized to THIAZOLIDINEDIONES.	1.99	1	0	thiazolidine
tridecanedioic acid tridecanedioic acid : An alpha,omega-dicarboxylic acid that is undecane substituted by carboxylic acid groups at positions C-1 and C-11.	2.01	1	0	alpha,omega-dicarboxylic acid	metabolite
hexacosanoic acid hexacosanoic acid: a C(26) saturated acid. hexacosanoic acid : A 26-carbon, straight-chain, saturated fatty acid.	2.25	1	0	fatty acid 26:0; straight-chain saturated fatty acid; very long-chain fatty acid
oleanolic acid [no description available]	5.48	14	1	hydroxy monocarboxylic acid; pentacyclic triterpenoid	plant metabolite
echothiophate iodide Echothiophate Iodide: A potent, long-acting cholinesterase inhibitor used as a miotic in the treatment of glaucoma.. ecothiopate iodide : The iodide salt of ecothiopate. An irreversible acetylcholinesterase inhibitor, it is used an ocular antihypertensive in the treatment of open-angle glaucoma, particularly when other drugs have proved inadequate.	2.35	2	0	iodide salt; quaternary ammonium salt	antiglaucoma drug; EC 3.1.1.8 (cholinesterase) inhibitor; miotic
2,3-dimethyl-1,3-butadiene 2,3-dimethyl-1,3-butadiene: structure in first source	2.11	1	0
podophyllotoxin Podophyllum: A genus of poisonous American herbs, family BERBERIDACEAE. The roots yield PODOPHYLLOTOXIN and other pharmacologically important agents. The plant was formerly used as a cholagogue and cathartic. It is different from the European mandrake, MANDRAGORA.	3.18	5	0	furonaphthodioxole; lignan; organic heterotetracyclic compound	antimitotic; antineoplastic agent; keratolytic drug; microtubule-destabilising agent; plant metabolite; tubulin modulator
hesperidin Hesperidin: A flavanone glycoside found in CITRUS fruit peels.. hesperidin : A disaccharide derivative that consists of hesperetin substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	4.9	1	1	3'-hydroxyflavanones; 4'-methoxyflavanones; dihydroxyflavanone; disaccharide derivative; flavanone glycoside; monomethoxyflavanone; rutinoside	mutagen
psilocybin Psilocybin: The major of two hallucinogenic components of Teonanacatl, the sacred mushroom of Mexico, the other component being psilocin. (From Merck Index, 11th ed). psilocybin : A tryptamine alkaloid that is N,N-dimethyltryptamine carrying an additional phosphoryloxy substituent at position 4. The major hallucinogenic alkaloid isolated from Psilocybe mushrooms (also known as Teonanacatl or "magic mushrooms").	2.31	1	0	organic phosphate; tertiary amino compound; tryptamine alkaloid	fungal metabolite; hallucinogen; prodrug; serotonergic agonist
medroxyprogesterone [no description available]	3.05	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.	3.47	2	0	17beta-hydroxy steroid; 17beta-hydroxyandrostan-3-one; 3-oxo-5alpha-steroid	androgen; Daphnia magna metabolite; human metabolite; mouse metabolite
flavone flavone: RN given refers to unlabeled cpd; structure given in first source. flavone : The simplest member of the class of flavones that consists of 4H-chromen-4-one bearing a phenyl substituent at position 2.	3.55	2	0	flavones	metabolite; nematicide
tryptophol tryptophol : An indolyl alcohol that is ethanol substituted by a 1H-indol-3-yl group at position 2.	2.03	1	0	indolyl alcohol	auxin; plant metabolite; Saccharomyces cerevisiae metabolite
hemimellitene hemimellitene: structure. 1,2,3-trimethylbenzene : A trimethylbenzene carrying methyl groups at positions 1, 2 and 3. It has been found in Centaurium erythraea.	2.04	1	0	trimethylbenzene	neurotoxin; plant metabolite
azomycin azomycin: RN given refers to parent cpd with specified locant; structure	2.49	2	0	C-nitro compound; imidazoles	antitubercular agent
uridine diphosphate n-acetylglucosamine Uridine Diphosphate N-Acetylglucosamine: Serves as the biological precursor of insect chitin, of muramic acid in bacterial cell walls, and of sialic acids in mammalian glycoproteins.	1.98	1	0
chamazulene chamazulene: structure	1.95	1	0	sesquiterpenoid
tropolone Tropolone: A seven-membered aromatic ring compound. It is structurally related to a number of naturally occurring antifungal compounds (ANTIFUNGAL AGENTS).. tropolone : A cyclic ketone that is cyclohepta-2,4,6-trien-1-one substituted by a hydroxy group at position 2. It is a toxin produced by the agricultural pathogen Burkholderia plantarii.	2.7	3	0	alpha-hydroxy ketone; cyclic ketone; enol	bacterial metabolite; fungicide; toxin
4,6-dinitro-o-cresol 4,6-dinitro-o-cresol: RN given refers to parent cpd; structure. 4,6-dinitro-o-cresol : A hydroxytoluene that is o-cresol carrying nitro substituents at positions 4 and 6.	2.31	1	0	dinitrophenol acaricide; hydroxytoluene; nitrotoluene	dinitrophenol insecticide; fungicide; herbicide
perillyl alcohol perillyl alcohol: inhibits geranylgeranyl transferase; structure in first source. perillyl alcohol : A limonene monoterpenoid consists of a cyclohexene ring substituted by a hydroxymethyl and a prop-1-en-2-yl group at positions 1 and 4 respectively. It is a constituent of a variety of essential oils including lavender.	2.05	1	0	limonene monoterpenoid	plant metabolite; volatile oil component
phenylacetylene phenylacetylene: can polymerize into DENDRIMERS	2.11	1	0	benzenes
methamphetamine Methamphetamine: A central nervous system stimulant and sympathomimetic with actions and uses similar to DEXTROAMPHETAMINE. The smokable form is a drug of abuse and is referred to as crank, crystal, crystal meth, ice, and speed.. methamphetamine : A member of the class of amphetamines in which the amino group of (S)-amphetamine carries a methyl substituent.	2.38	2	0	amphetamines; secondary amine	central nervous system stimulant; environmental contaminant; neurotoxin; psychotropic drug; xenobiotic
dicyclohexylcarbodiimide 1,3-dicyclohexylcarbodiimide : A carbodiimide compound having a cyclohexyl substituent on both nitrogen atoms.	2.07	1	0	carbodiimide	ATP synthase inhibitor; cross-linking reagent; peptide coupling reagent
1-chloropropane 1-chloropropane: structure in first source	2.04	1	0
2,2,4-trimethylpentane 2,2,4-trimethylpentane: nephrotoxic. isooctane : An alkane that consists of pentane bearing two methyl substituents at position 2 and a single methyl substituent at position 4.	2.04	1	0	alkane; volatile organic compound	fuel additive; nephrotoxin; non-polar solvent
tert-butyl acetate [no description available]	2	1	0
3-aminobutyric acid 3-aminobutyric acid: GABA uptake inhibitor. 3-aminobutanoic acid : A beta-amino acid that is butyric acid which is substituted by an amino group at position 3.	3.86	11	0	amino acid zwitterion; beta-amino acid; monocarboxylic acid	metabolite
maleimide [no description available]	3.03	4	0	dicarboximide; maleimides	EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
1,3-dichlorobenzene 1,3-dichlorobenzene : A dichlorobenzene carrying chloro substituents at positions 1 and 3.	2.04	1	0	dichlorobenzene
muscone muscone: structure in first source	2.02	1	0
malondialdehyde Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.	5.17	42	0	dialdehyde	biomarker
1-chlorohexane [no description available]	2.04	1	0
3-hexen-1-ol 3-hexen-1-ol: RN given refers to (Z)-isomer; a green odor chemical. hex-3-en-1-ol : A primary alcohol that is hex-3-ene substituted by a hydroxy group at position 1.	3.18	5	0	alkenyl alcohol; homoallylic alcohol; primary alcohol; volatile organic compound	plant metabolite
myristic acid Myristic Acid: A saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. It is used to synthesize flavor and as an ingredient in soaps and cosmetics. (From Dorland, 28th ed). tetradecanoic acid : A straight-chain, fourteen-carbon, long-chain saturated fatty acid mostly found in milk fat.. tetradecanoate : A long-chain fatty acid anion that is the conjugate base of myristic acid; major species at pH 7.3.	3.1	5	0	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite
n-hexadecane n-hexadecane: structure. hexadecane : A straight-chain alkane with 16 carbon atoms. It is a component of essential oil isolated from long pepper.	1.98	1	0	long-chain alkane	non-polar solvent; plant metabolite; volatile oil component
4,4'-bipyridyl 4,4'-bipyridine : A bipyridine in which the two pyridine moieties are linked by a bond between positions C-4 and C-4'.	2.07	1	0	bipyridine
4-chloromercuribenzenesulfonate 4-Chloromercuribenzenesulfonate: A cytotoxic sulfhydryl reagent that inhibits several subcellular metabolic systems and is used as a tool in cellular physiology.	2.03	1	0	arenesulfonic acid; arylmercury compound
beta-phellandrene [no description available]	2.47	2	0	phellandrene	plant metabolite
perfluorocyclopentene perfluorocyclopentene: structure in first source	5.07	7	0
4-methyl-1-(1-methylethyl)-3-cyclohexen-1-ol 4-methyl-1-(1-methylethyl)-3-cyclohexen-1-ol: structure in first source. 4-terpineol : A terpineol that is 1-menthene carrying a hydroxy substituent at position 4.	2.31	1	0	terpineol; tertiary alcohol	anti-inflammatory agent; antibacterial agent; antineoplastic agent; antioxidant; antiparasitic agent; apoptosis inducer; plant metabolite; volatile oil component
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	1	0	glycerophosphocholine
formestane [no description available]	1.98	1	0	17-oxo steroid; 3-oxo-Delta(4) steroid; enol; hydroxy steroid	antineoplastic agent; EC 1.14.14.14 (aromatase) inhibitor
6-methylsalicylic acid 6-methylsalicylic acid: structure. 6-methylsalicylic acid : A monohydroxybenzoic acid that is salicylic acid in which the hydrogen ortho to the carboxylic acid group is substituted by a methyl group.	2.03	1	0	monohydroxybenzoic acid	Penicillium metabolite; plant metabolite
1,4-dimethylnaphthalene 1,4-dimethylnaphthalene : A dimethylnaphthalene carrying methyl groups at positions 1 and 4.	2.04	1	0	dimethylnaphthalene
3-hydroxyflavone 3-hydroxyflavone: structure given in first source. flavonol : A monohydroxyflavone that is the 3-hydroxy derivative of flavone.	6.72	16	1	flavonols; monohydroxyflavone
2,6-dimethylnaphthalene 2,6-dimethylnaphthalene: RN given refers to parent cpd. 2,6-dimethylnaphthalene : A dimethylnaphthalene carrying methyl groups at positions 2 and 6.	2.04	1	0	dimethylnaphthalene	environmental contaminant
anatabine anatabine: alkaloid found in tobacco; structure	3.02	4	0	bipyridines
1,2-dibromobenzene dibromobenzene : Any member of the class of bromobenzenes that consists of a benzene or a substituted benzene ring carrying two bromo groups at unspecified positions.	2.04	1	0	dibromobenzene
allethrins Allethrins: Synthetic analogs of the naturally occurring insecticides cinerin, jasmolin, and pyrethrin. (From Merck Index, 11th ed)	2.02	1	0	cyclopropanecarboxylate ester	pyrethroid ester insecticide
diphenylamine Diphenylamine: In humans it may be irritating to mucous membranes. Methemoglobinemia has been produced experimentally. In veterinary use, it is one of active ingredients in topical agents for prevention and treatment of screwworm infestation. An indicator in tests for nitrate poisoning.. diphenylamine : An aromatic amine containing two phenyl substituents. It has been used as a fungicide for the treatment of superficial scald in apples and pears, but is no longer approved for this purpose within the European Union.	4.9	1	1	aromatic amine; bridged diphenyl fungicide; secondary amino compound	antifungal agrochemical; antioxidant; carotogenesis inhibitor; EC 1.3.99.29 [phytoene desaturase (zeta-carotene-forming)] inhibitor; ferroptosis inhibitor; radical scavenger
iodobenzene iodobenzene: RN given refers to unlabeled parent cpd	2.44	2	0
1-hexene 1-hexene: structure in first source. 1-hexene : An alkene that is hexane carrying a double bond at position 1.	2.46	2	0	alkene
1,3-cyclohexadiene 1,3-cyclohexadiene: structure given in first source	2.03	1	0	cyclohexadiene
fluoromethane fluoromethane: RN given refers to parent cpd. fluorocarbon : Compounds consisting wholly of fluorine and carbon.. fluoromethane : A member of the class of fluoromethanes that is methane in which a single hydrogen is substituted by a fluorine atom.	2.13	1	0	fluorohydrocarbon; fluoromethanes; methyl halides	refrigerant
1-methylcyclopropane 1-methylcyclopropane: do not confuse with MCP cpd (1-methylcyclopropene)	2.41	2	0
2,2-dimethylmalonate dimethylmalonic acid : A dicarboxylic acid that is malonic acid in which both methylene hydrogens have been replaced by methyl groups.	2.08	1	0	dicarboxylic acid	fatty acid synthesis inhibitor
triphenylphosphine triphenylphosphine: RN given refers to parent cpd. triphenylphosphine : A member of the class of tertiary phosphines that is phosphane in which the three hydrogens are replaced by phenyl groups.	2.48	2	0	benzenes; tertiary phosphine	NMR chemical shift reference compound; reducing agent
pentachlorobenzene pentachlorobenzene: structure. pentachlorobenzene : A member of the class of pentachlorobenzenes that is benzene in which five of the hydrogens are replaced by chlorines. Now classed as a persistent organic pollutant under the Stockholm Convention.	2.04	1	0	pentachlorobenzenes	persistent organic pollutant
2-methylanthracene 2-methylanthracene: structure given in first source	2.04	1	0
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	3.86	12	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
chorismic acid Chorismic Acid: A cyclohexadiene carboxylic acid derived from SHIKIMIC ACID and a precursor for the biosynthesis of UBIQUINONE and the AROMATIC AMINO ACIDS.. chorismic acid : The (3R,4R)-stereoisomer of 5-[(1-carboxyethenyl)oxy]-6-hydroxycyclohexa-1,3-diene-1-carboxylic acid.	2.31	1	0	5-[(1-carboxyethenyl)oxy]-6-hydroxycyclohexa-1,3-diene-1-carboxylic acid	Escherichia coli metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
diazoacetic ester diazoacetic ester: structure	2.06	1	0
1,4-cyclohexadiene [no description available]	2.11	1	0	cyclohexadiene
ethyl palmitate ethyl hexadecanoate : A long-chain fatty acid ethyl ester resulting from the formal condensation of the carboxy group of palmitic acid with the hydroxy group of ethanol.	2.03	1	0	hexadecanoate ester; long-chain fatty acid ethyl ester	plant metabolite
n-tetradecane tetradecane : A straight chain alkane consisting of 14 carbon atoms.	2.41	1	0	long-chain alkane	plant metabolite; volatile oil component
1,2,3,4-tetrachlorobenzene 1,2,3,4-tetrachlorobenzene : A tetrachlorobenzene carrying chloro groups at positions 1, 2 , 3 and 4.. tetrachlorobenzene : Any member of the class of chlorobenzenes carrying four chloro groups at unspecified positions.	2.04	1	0	tetrachlorobenzene
1,2,3,5-tetrachlorobenzene 1,2,3,5-tetrachlorobenzene : A tetrachlorobenzene carrying chloro groups at positions 1, 2, 3 and 5.	2.04	1	0	tetrachlorobenzene
4-methoxystyrene 4-methoxystyrene: structure in first source	2.07	1	0
homoserine homoserine : An alpha-amino acid that is glycine substituted at the alpha-position by a 2-hydroxyethyl group.. L-homoserine : The L-enantiomer of homoserine.	4.02	4	0	amino acid zwitterion; homoserine	algal metabolite; Escherichia coli metabolite; human metabolite; Saccharomyces cerevisiae metabolite
nitrosoguanidines Nitrosoguanidines: Nitrosylated derivatives of guanidine. They are used as MUTAGENS in MOLECULAR BIOLOGY research.	1.94	1	0
2-piperidone 2-piperidone: structure given in first source. piperidin-2-one : A delta-lactam that is piperidine which is substituted by an oxo group at position 2.	2.68	3	0	delta-lactam; piperidones	EC 1.2.1.88 (L-glutamate gamma-semialdehyde dehydrogenase) inhibitor
dodecanedioic acid dodecanedioic acid: RN given refers to parent cpd. dodecanedioic acid : An alpha,omega-dicarboxylic acid that is dodecane in which the methyl groups have been oxidised to the corresponding carboxylic acids.	2.01	1	0	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	EC 1.1.1.1 (alcohol dehydrogenase) inhibitor; human metabolite
pyridine n-oxide pyridine N-oxide: RN given refers to parent cpd. pyridine N-oxide : The pyridine N-oxide derived from the parent pyridine. It is a drug metabolite of the antihypertensive agent pinacidil.	2.03	1	0	pyridine N-oxides	drug metabolite
diphenyliodonium diphenyliodonium: RN given refers to the parent coumpound; inhibitor of neutrophil superoxide generating oxidase; structure has been determined	2.5	2	0
acetylenedicarboxylic acid dimethyl ester acetylenedicarboxylic acid dimethyl ester: inhibitor of oxidative phosphorylation	2.02	1	0
9-methylanthracene [no description available]	2.04	1	0
9,10-dimethylanthracene 9,10-dimethylanthracene: RN given refers to parent ion	2.44	2	0
levonorgestrel Levonorgestrel: A synthetic progestational hormone with actions similar to those of PROGESTERONE and about twice as potent as its racemic or (+-)-isomer (NORGESTREL). It is used for contraception, control of menstrual disorders, and treatment of endometriosis.	2.31	1	0	17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; terminal acetylenic compound	contraceptive drug; female contraceptive drug; progestin; synthetic oral contraceptive
cyclopentenone 2-cyclopenten-1-one : An enone that is cyclopentanone having a C=C double bond at position 2.	10.9	309	0	alicyclic ketone; enone	Hsp70 inducer
2-cyclohexen-1-one 2-cyclohexen-1-one: RN given refers to unlabeled cpd with specified locant for double bond. cyclohexenone : The parent compound of the cyclohexenones, composed of cyclohexanone having one double bond in the ring.. cyclohex-2-enone : A cyclohexenone having its C=C double bond at the 2-position.	2.41	2	0	cyclohexenone
1,2,3,4-tetrahydrocarbazole 1,2,3,4-tetrahydrocarbazole: structure in first source	2.45	2	0
deoxycytidine [no description available]	2.69	3	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
deoxyuridine [no description available]	3.58	9	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
cytidine diphosphate choline Cytidine Diphosphate Choline: Donor of choline in biosynthesis of choline-containing phosphoglycerides.	1.98	1	0	nucleotide-(amino alcohol)s; phosphocholines	human metabolite; mouse metabolite; neuroprotective agent; psychotropic drug; Saccharomyces cerevisiae metabolite
chlormequat Chlormequat: A plant growth regulator that is commonly used on ornamental plants.. chlormequat : A quaternary ammonium ion that is choline in which the hydroxy group has been replaced by a chlorine. Its salts (particularly the chloride salt, known as chlormequat chloride) are used as plant growth retardants.	2.17	1	0	quaternary ammonium ion	plant growth retardant
2-phenylpyridine 2-phenylpyridine: structure given in first source	2.07	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.	2.04	1	0
undecane undecane : A straight-chain alkane with 11 carbon atoms.	2.04	1	0	alkane
phenazocine Phenazocine: An opioid analgesic with actions and uses similar to MORPHINE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1095)	2.9	4	0
durapatite Durapatite: The mineral component of bones and teeth; it has been used therapeutically as a prosthetic aid and in the prevention and treatment of osteoporosis.. hydroxylapatite : A phosphate mineral with the formula Ca5(PO4)3(OH).	2.42	2	0
cadmium sulfide [no description available]	2.03	1	0	cadmium molecular entity
potassium hydroxide potassium hydroxide: RN given refers to cpd with MF of K-OH	2.59	2	0	alkali metal hydroxide
zinc oxide Zinc Oxide: A mild astringent and topical protectant with some antiseptic action. It is also used in bandages, pastes, ointments, dental cements, and as a sunblock.	2.52	2	0	zinc molecular entity
beta-pinene beta-pinene: alpha-pinene is also available. beta-pinene : An isomer of pinene with an exocyclic double bond. It is a component of essential oils from many plants.	3.19	5	0	pinene	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.	4.41	20	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]	3.44	7	0
propanidid Propanidid: An intravenous anesthetic that has been used for rapid induction of anesthesia and for maintenance of anesthesia of short duration. (From Martindale, The Extra Pharmacopoeia, 30th ed, p918)	1.94	1	0	methoxybenzenes
pseudouridine [no description available]	6.95	1	0	pseudouridines	fundamental metabolite
vincamine Vincamine: A major alkaloid of Vinca minor L., Apocynaceae. It has been used therapeutically as a vasodilator and antihypertensive agent, particularly in cerebrovascular disorders.	2.15	1	0	alkaloid ester; hemiaminal; methyl ester; organic heteropentacyclic compound; vinca alkaloid	antihypertensive agent; metabolite; vasodilator agent
1-pentene-3-one 1-penten-3-one : An enone that is pent-1-ene substituted by an oxo group at position 3.	2.02	1	0	enone	flavouring agent; genotoxin; human metabolite; plant metabolite
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.	1.98	1	0	12beta-hydroxy steroid; 14beta-hydroxy steroid; 3beta-hydroxy steroid; 3beta-sterol	hapten; plant metabolite
bromoxynil bromoxynil: RN given refers to parent cpd; structure. 3,5-dibromo-4-hydroxybenzonitrile : A dibromobenzene that is 2,6-dibromophenol substituted by a cyano group at position 4.	2.02	1	0	dibromobenzene; hydroxynitrile; phenols	environmental contaminant; herbicide; xenobiotic
6-methylchrysene 6-methylchrysene: RN given refers to parent cpd; structure given in first source	2.04	1	0	carbopolycyclic compound
decane decane : A straight-chain alkane with 10 carbon atoms.	2.46	2	0	alkane
3-methylcyclopentanone [no description available]	3.46	7	0	cyclopentanones
2,2'-biphenol biphenyl-2,2'-diol : A member of the class of hydroxybiphenyls carrying hydroxy groups at positions 2 and 2'.	2.21	1	0	hydroxybiphenyls
9,10-epoxystearic acid 9,10-epoxystearic acid: RN given refers to parent cpd with unspecified isomeric designation; structure. 9,10-epoxyoctadecanoic acid : An epoxy fatty acid consisting of octadecanoic (stearic) acid with a single epoxide located between positions 9 and 10.	2.02	1	0	epoxystearic acid	human metabolite
tetrachloroisophthalonitrile tetrachloroisophthalonitrile: structure. chlorothalonil : A dinitrile that is benzene-1,3-dicarbonitrile substituted by four chloro groups. A non-systemic fungicide first introduced in the 1960s, it is used to control a range of diseases in a wide variety of crops.	2.66	2	0	aromatic fungicide; dinitrile; tetrachlorobenzene	antifungal agrochemical
paraquat Paraquat: A poisonous dipyridilium compound used as contact herbicide. Contact with concentrated solutions causes irritation of the skin, cracking and shedding of the nails, and delayed healing of cuts and wounds.. paraquat : An organic cation that consists of 4,4'-bipyridine bearing two N-methyl substituents loctated at the 1- and 1'-positions.	4.05	14	0	organic cation	geroprotector; herbicide
picloram Picloram: A picolinic acid derivative that is used as a herbicide.. picloram : A pyridinemonocarboxylic acid that is pyridine-2-carboxylic acid which is substituted by a chloro group at positions 3,5 and 6, and by an amino group at position 4. It is a systemic herbicide used to control deeply rooted herbaceous weeds and woody plants in rights-of-way, forestry, range lands, pastures, and small grain crops.	2.08	1	0	aminopyridine; chloropyridine; organochlorine pesticide; pyridinemonocarboxylic acid	herbicide; synthetic auxin
s,n,n'-tripropylthiocarbamate Reward: An object or a situation that can serve to reinforce a response, to satisfy a motive, or to afford pleasure.. vernolate : A monounsaturated fatty acid anion that is the conjugate base of vernolic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.	2.95	4	0	tertiary amine
tetrabutylammonium tetrabutylammonium: lipophilic probe; RN given refers to parent cpd	2.06	1	0	quaternary ammonium ion
dronabinol Dronabinol: A psychoactive compound extracted from the resin of Cannabis sativa (marihuana, hashish). The isomer delta-9-tetrahydrocannabinol (THC) is considered the most active form, producing characteristic mood and perceptual changes associated with this compound.. Delta(9)-tetrahydrocannabinol : A diterpenoid that is 6a,7,8,10a-tetrahydro-6H-benzo[c]chromene substituted at position 1 by a hydroxy group, positions 6, 6 and 9 by methyl groups and at position 3 by a pentyl group. The principal psychoactive constituent of the cannabis plant, it is used for treatment of anorexia associated with AIDS as well as nausea and vomiting associated with cancer chemotherapy.	2.05	1	0	benzochromene; diterpenoid; phytocannabinoid; polyketide	cannabinoid receptor agonist; epitope; hallucinogen; metabolite; non-narcotic analgesic
hexadecyldimethylamine hexadecyldimethylamine: has antifungal activity; isolated from Arthrobacter agilis; structure in first source	2.58	2	0
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.	3.09	5	0	aromatic amine; guanidines; organochlorine compound; pyrazines	diuretic; sodium channel blocker
perillaldehyde perillaldehyde: from oil of Perillae herba; has neuropharmacological actions; RN given refers to cpd without isomeric designation; structure in Merck Index, 9th ed, #6956. perillyl aldehyde : An aldehyde that is cyclohex-1-ene-1-carbaldehyde substituted by a prop-1-en-2-yl group at position 4.	2.06	1	0	aldehyde; olefinic compound	human metabolite; mouse metabolite; volatile oil component
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.	3.34	1	1	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
2,4-diacetylphloroglucinol 2,4-diacetylphloroglucinol: produced by Pseudomonas aurantiaca. 2,4-diacetylphloroglucinol : A benzenetriol that is phloroglucinol in which two of the ring hydrogens are replaced by acetyl groups.	2.01	1	0	aromatic ketone; benzenetriol; diketone; methyl ketone	antifungal agent; bacterial metabolite
phenethyl isothiocyanate phenethyl isothiocyanate: a dietary liver aldehyde dehydrogenase inhibitor; promotes urinary bladder carcinoma. phenethyl isothiocyanate : An isothiocyanate having a phenethyl group attached to the nitrogen. It is a naturally occurring compound found in some cruciferous vegetables (e.g. watercress) and is known to possess anticancer properties.	2.08	1	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.	2.41	2	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.	1.95	1	0	chlorocarbon; organochlorine insecticide	persistent organic pollutant
12-methylbenzanthracene [no description available]	2.04	1	0
1-tridecene [no description available]	2.02	1	0	acyclic olefin
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.	3.36	7	0	fucopyranose; L-fucose	Escherichia coli metabolite; mouse metabolite
acetosyringone acetosyringone: plant inducer which induces expression of VirE & VirG in A. tumefaciens. acetosyringone : A member of the class of acetophenones that is 1-phenylethanone substituted by a hydroxy group at position 4 and methoxy groups at positions 3 and 5.	2.1	1	0	acetophenones; dimethoxybenzene; phenols	anti-asthmatic drug; non-narcotic analgesic; non-steroidal anti-inflammatory drug; peripheral nervous system drug; plant metabolite
2-methylphenanthrene [no description available]	2.04	1	0
chloroflurenol-methyl [no description available]	2.03	1	0
7-methylbenzanthracene [no description available]	2.04	1	0
benzyl acetone benzyl acetone: a dominant floral attractant	2.53	2	0	ketone
stavudine Stavudine: A dideoxynucleoside analog that inhibits reverse transcriptase and has in vitro activity against HIV.. stavudine : A nucleoside analogue obtained by formal dehydration across positions 2 and 3 of thymidine. An inhibitor of HIV-1 reverse transcriptase	2.07	1	0	dihydrofuran; nucleoside analogue; organic molecular entity	antimetabolite; antiviral agent; EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
methional [no description available]	2.15	1	0	aliphatic sulfide	prostaglandin antagonist
2,2-bis(bromomethyl)-1,3-propanediol 2,2-bis(bromomethyl)-1,3-propanediol: structure given in first source	3.92	12	0	primary alcohol
fluorescein-5-isothiocyanate Fluorescein-5-isothiocyanate: Fluorescent probe capable of being conjugated to tissue and proteins. It is used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.. fluorescein 5-isothiocyanate : The 5-isomer of fluorescein isothiocyanate. Acts as a fluorescent probe capable of being conjugated to tissue and proteins; used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.	2.91	4	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.	4.74	27	0	thujene	plant metabolite
2,3-diketogulonic acid 2,3-Diketogulonic Acid: Metabolite of ASCORBIC ACID and the oxidized form of the lactone DEHYDROASCORBIC ACID.. 2,3-diketogulonic acid : A carbohydrate acid formally derived from gulonic acid by oxidation of the -OH groups at positions 2 and 3 to keto groups.	1.97	1	0
mannose mannopyranose : The pyranose form of mannose.	4.14	16	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.	5.86	7	1	1,4-dimercaptobutane-2,3-diol; butanediols; dithiol; glycol; thiol	chelator; human metabolite; reducing agent
cyclazocine Cyclazocine: An analgesic with mixed narcotic agonist-antagonist properties.	3.78	3	0
phenoxyacetic acid phenoxyacetic acid : A monocarboxylic acid that is the O-phenyl derivative of glycolic acid. A metabolite of 2-phenoxyethanol, it is used in the manufacture of pharmaceuticals, pesticides, fungicides and dyes.	2.57	2	0	aromatic ether; monocarboxylic acid	allergen; Aspergillus metabolite; human xenobiotic metabolite; plant growth retardant
furaneol furaneol: RN given refers to compound with no isomeric designation. 4-hydroxy-2,5-dimethylfuran-3-one : A member of the class of furans that is 2,5-dimethylfuran carrying additional oxo and hydroxy groups at positions 3 and 4 respectively. It has been found particularly in strawberries and other such fruits.	2.45	2	0	cyclic ketone; enol; furans	flavouring agent; fragrance; plant metabolite
5-methylchrysene 5-methylchrysene: methylchrysenes in tobacco smoke are suspected to contribute to tumorigenicity of this inhalant; RN given refers to unlabeled cpd; structure	2.04	1	0	carbopolycyclic compound
5,6-dimethylchrysene 5,6-dimethylchrysene: structure given in first source	2.04	1	0
7-ethylbenz(a)anthracene [no description available]	2.04	1	0
tranylcypromine Tranylcypromine: A propylamine formed from the cyclization of the side chain of amphetamine. This monoamine oxidase inhibitor is effective in the treatment of major depression, dysthymic disorder, and atypical depression. It also is useful in panic and phobic disorders. (From AMA Drug Evaluations Annual, 1994, p311). tranylcypromine : A racemate comprising equal amounts of (1R,2S)- and (1S,2R)-2-phenylcyclopropan-1-amine. An irreversible monoamine oxidase inhibitor that is used as an antidepressant (INN tranylcypromine).. (1R,2S)-tranylcypromine : A 2-phenylcyclopropan-1-amine that is the (1R,2S)-enantiomer of tranylcypromine.	1.94	1	0	2-phenylcyclopropan-1-amine
denatonium benzoate [no description available]	1.98	1	0
streptomycin [no description available]	2.34	2	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.	3.41	7	0	carbon oxoanion
2-octanol 2-octanol: RN given refers to cpd without isomeric designation. octan-2-ol : An octanol carrying the hydroxy group at position 2.	1.92	1	0	octanol; secondary alcohol	plant metabolite; volatile oil component
tabersonine [no description available]	2.44	2	0	alkaloid ester; methyl ester; monoterpenoid indole alkaloid; organic heteropentacyclic compound	antineoplastic agent; metabolite
carbenicillin Carbenicillin: Broad-spectrum semisynthetic penicillin derivative used parenterally. It is susceptible to gastric juice and penicillinase and may damage platelet function.. carbenicillin : A penicillin antibiotic having a 6beta-2-carboxy-2-phenylacetamido side-chain.	1.94	1	0	penicillin allergen; penicillin	antibacterial drug
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.	2.42	2	0	diastereoisomeric mixture; homocysteines; non-proteinogenic alpha-amino acid; sulfoximide	EC 6.3.2.2 (glutamate--cysteine ligase) inhibitor; ferroptosis inducer
norleucine Norleucine: An unnatural amino acid that is used experimentally to study protein structure and function. It is structurally similar to METHIONINE, however it does not contain SULFUR.. L-norleucine : A non-proteinogenic L-alpha-amino acid comprising hexanoic acid carrying an amino group at C-2. It does not occur naturally.	1.95	1	0	2-aminohexanoic acid; L-alpha-amino acid zwitterion; non-proteinogenic L-alpha-amino acid
dihydrostreptomycin sulfate Dihydrostreptomycin Sulfate: A semi-synthetic aminoglycoside antibiotic that is used in the treatment of TUBERCULOSIS.	1.93	1	0
vidarabine adenine arabinoside : A purine nucleoside in which adenine is attached to arabinofuranose via a beta-N(9)-glycosidic bond.	1.97	1	0	beta-D-arabinoside; purine nucleoside	antineoplastic agent; bacterial metabolite; nucleoside antibiotic
iprindole Iprindole: A tricyclic antidepressant that has actions and uses similar to those of AMITRIPTYLINE, but has only weak antimuscarinic and sedative effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p257)	1.97	1	0	indoles
iodinated glycerol iodinated glycerol: secretolytic agent; RN given refers to cpd without iodine locant	2.01	1	0	dioxolane
limonene Limonene: A naturally-occurring class of MONOTERPENES which occur as a clear colorless liquid at room temperature. Limonene is the major component in the oil of oranges which has many uses, including as flavor and fragrance. It is recognized as safe in food by the Food and Drug Administration (FDA).. limonene : A monoterpene that is cyclohex-1-ene substituted by a methyl group at position 1 and a prop-1-en-2-yl group at position 4 respectively.	3.3	6	0	cycloalkene; p-menthadiene	human metabolite
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.	4.87	13	0	amino dicarboxylic acid; D-alpha-amino acid; D-aspartic acid derivative; secondary amino compound	neurotransmitter agent
ammonium nitrate ammonium nitrate: structure. ammonium nitrate : The ammonium salt of nitric acid.	2.06	1	0	ammonium salt; inorganic molecular entity; inorganic nitrate salt	explosive; fertilizer; oxidising agent
helenalin helenalin: toxic principle of Helenium microcephalum (smallhead sneezeweed); structure. helenalin : A sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by a hydroxy group at position 4, methyl groups at positions 4a and 8 and a methylidene group at position 3 (the 3aS,4S,4aR,7aR,8R,9aR stereoisomer).. NF-kappaB inhibitor : An inhibitor of NF-kappaB (nuclear factor kappa-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA.	2.36	2	0	cyclic ketone; gamma-lactone; organic heterotricyclic compound; secondary alcohol; sesquiterpene lactone	anti-inflammatory agent; antineoplastic agent; metabolite; plant metabolite
sodium metasilicate sodium metasilicate: RN given refers to silicic acid, di-Na salt. sodium silicate : An inorganic sodium salt having silicate as the counterion.	2.06	1	0	inorganic sodium salt
propargyl ether propargyl ether: structure in first source	3.19	1	0
terodiline [no description available]	1.99	1	0	diarylmethane
hepes [no description available]	2	1	0	HEPES; organosulfonic acid
dysprosium Dysprosium: An element of the rare earth family that has the atomic symbol Dy, atomic number 66, and atomic weight 162.50. Dysprosium is a silvery metal used primarily in the form of various salts.	2.47	2	0	f-block element atom; lanthanoid atom
iridium Iridium: A metallic element with the atomic symbol Ir, atomic number 77, and atomic weight 192.22.	8.78	10	0	cobalt group element atom; platinum group metal atom
lanthanum [no description available]	3.57	8	0	f-block element atom; lanthanoid atom; scandium group element atom
lutetium Lutetium: An element of the rare earth family of metals. It has the atomic symbol Lu, atomic number 71, and atomic weight 175.	2.05	1	0	d-block element atom; lanthanoid 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.	4.87	11	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.	2.88	4	0	elemental mercury; zinc group element atom	neurotoxin
molybdenum Molybdenum: A metallic element with the atomic symbol Mo, atomic number 42, and atomic weight 95.95. It is an essential trace element, being a component of the enzymes xanthine oxidase, aldehyde oxidase, and nitrate reductase.	3.55	8	0	chromium group element atom	micronutrient
niobium Niobium: A metal element atomic number 41, atomic weight 92.906, symbol Nb.	2.08	1	0	vanadium group element atom
osmium Osmium: A very hard, gray, toxic, and nearly infusible metal element, atomic number 76, atomic weight 190.2, symbol Os.	2.38	2	0	iron group element atom; platinum group metal atom
palladium Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.	7.04	58	0	metal allergen; nickel group element atom; platinum group metal atom
platinum Platinum: A heavy, soft, whitish metal, resembling tin, with atomic number 78, atomic weight 195.084, symbol Pt. It is used in manufacturing equipment for laboratory and industrial use. It occurs as a black powder (platinum black) and as a spongy substance (spongy platinum) and may have been known in Pliny's time as alutiae.	7.95	4	0	elemental platinum; nickel group element atom; platinum group metal atom
rhenium Rhenium: A metal, atomic number 75, atomic weight 186.207, symbol Re.	4.3	18	0	manganese group element atom
rhodium Rhodium: A hard and rare metal of the platinum group, atomic number 45, atomic weight 102.905, symbol Rh.. rhodium atom : A cobalt group element atom of atomic number 45.	10.32	50	0	cobalt group element atom
ruthenium Ruthenium: A hard, brittle, grayish-white rare earth metal with an atomic symbol Ru, atomic number 44, and atomic weight 101.07. It is used as a catalyst and hardener for PLATINUM and PALLADIUM.	13.47	33	1	iron group element atom; platinum group metal atom
samarium Samarium: An element of the rare earth family of metals. It has the atomic symbol Sm, atomic number 62, and atomic weight 150.36. The oxide is used in the control rods of some nuclear reactors.	7.93	4	0	f-block element atom; lanthanoid atom
scandium Scandium: An element of the rare earth family of metals. It has the atomic symbol Sc, atomic number 21, and atomic weight 45.	7.77	3	0	d-block element atom; rare earth metal atom; scandium group element atom
silver Silver: An element with the atomic symbol Ag, atomic number 47, and atomic weight 107.87. It is a soft metal that is used medically in surgical instruments, dental prostheses, and alloys. Long-continued use of silver salts can lead to a form of poisoning known as ARGYRIA.	6.68	16	1	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.	2.95	4	0	manganese group element atom
thorium Thorium: A radioactive element of the actinide series of metals. It has an atomic symbol Th, atomic number 90, and atomic weight 232.04. It is used as fuel in nuclear reactors to produce fissionable uranium isotopes. Because of its radioopacity, various thorium compounds are used to facilitate visualization in roentgenography.	2.53	2	0	actinoid atom; f-block element atom
titanium Titanium: A dark-gray, metallic element of widespread distribution but occurring in small amounts with atomic number, 22, atomic weight, 47.867 and symbol, Ti; specific gravity, 4.5; used for fixation of fractures.	6.94	21	1	titanium group element atom
tungsten Tungsten: A metallic element with the atomic symbol W, atomic number 74, and atomic weight 183.85. It is used in many manufacturing applications, including increasing the hardness, toughness, and tensile strength of steel; manufacture of filaments for incandescent light bulbs; and in contact points for automotive and electrical apparatus.	2.95	4	0	chromium group element atom	micronutrient
argon Argon: A noble gas with the atomic symbol Ar, atomic number 18, and atomic weight 39.948. It is used in fluorescent tubes and wherever an inert atmosphere is desired and nitrogen cannot be used.	2.97	4	0	monoatomic argon; noble gas atom; p-block element atom	food packaging gas; neuroprotective agent
arsine arsine: structure. arsine : Arsane (AsH3) and compounds derived from it by substituting one, two or three hydrogen atoms by hydrocarbyl groups: RAsH2, R2AsH, R3As (R =/= H) are called primary, secondary and tertiary arsines, respectively. A specific arsine is preferably named as a substituted arsane.	3.15	1	0	arsanes; arsine; mononuclear parent hydride
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.	4.83	30	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.	2.76	3	0	f-block element atom; lanthanoid atom
chromium Chromium: A trace element that plays a role in glucose metabolism. It has the atomic symbol Cr, atomic number 24, and atomic weight 52. According to the Fourth Annual Report on Carcinogens (NTP85-002,1985), chromium and some of its compounds have been listed as known carcinogens.. chromium ion : An chromium atom having a net electric charge.. chromium atom : A chromium group element atom that has atomic number 24.	4.62	8	0	chromium group element atom; metal allergen	micronutrient
europium Europium: An element of the rare earth family of metals. It has the atomic symbol Eu, atomic number 63, and atomic weight 152. Europium is used in the form of its salts as coatings for cathode ray tubes and in the form of its organic derivatives as shift reagents in NMR spectroscopy.	2.08	1	0	f-block element atom; lanthanoid atom
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.	2.98	4	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.	9.49	21	0	copper group element atom; elemental gold
hafnium Hafnium: A metal element of atomic number 72 and atomic weight 178.49, symbol Hf.	2.03	1	0	titanium group element atom
helium Helium: A noble gas with the atomic symbol He, atomic number 2, and atomic weight 4.003. It is a colorless, odorless, tasteless gas that is not combustible and does not support combustion. It was first detected in the sun and is now obtained from natural gas. Medically it is used as a diluent for other gases, being especially useful with oxygen in the treatment of certain cases of respiratory obstruction, and as a vehicle for general anesthetics.	2.06	1	0	monoatomic helium; noble gas atom; s-block element atom	food packaging gas
uranium Uranium: A radioactive element of the actinide series of metals. It has an atomic symbol U, atomic number 92, and atomic weight 238.03. U-235 is used as the fissionable fuel in nuclear weapons and as fuel in nuclear power reactors.	2.43	2	0	actinoid atom; f-block element atom; monoatomic uranium
vanadium Vanadium: A metallic element with the atomic symbol V, atomic number 23, and atomic weight 50.94. It is used in the manufacture of vanadium steel. Prolonged exposure can lead to chronic intoxication caused by absorption usually via the lungs.	2.75	3	0	elemental vanadium; vanadium group element atom	micronutrient
xenon Xenon: A noble gas with the atomic symbol Xe, atomic number 54, and atomic weight 131.30. It is found in the earth's atmosphere and has been used as an anesthetic.	2.11	1	0	monoatomic xenon; noble gas atom; p-block element atom
zirconium Zirconium: A rather rare metallic element with atomic number 40, atomic weight 91.224, and symbol Zr.	3.74	10	0	titanium group element atom
aluminum chloride Aluminum Chloride: A compound with the chemical formula AlCl3; the anhydrous salt is used as a catalyst in organic chemical synthesis, and hydrated salts are used topically as antiperspirants, and for the management of HYPERHYDROSIS.	2.03	1	0	aluminium coordination entity	Lewis acid
cupric chloride cupric chloride: RN given refers to unlabeled parent cpd. copper(II) chloride : An inorganic chloride of copper in which the metal is in the +2 oxidation state.	3.11	5	0	copper molecular entity; inorganic chloride	EC 5.3.3.5 (cholestenol Delta-isomerase) 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.	2.42	2	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.	2.91	4	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.	1.99	1	0	D-galactosamine; primary amino compound	toxin
titanium tetrachloride titanium tetrachloride: RN given refers to TiCl4	2.05	1	0
palladium chloride palladium chloride: RN given refers to parent cpd; structure. palladium(II) chloride : A palladium coordination entity consisting of palladium(II) bound to two chlorine atoms.	2.03	1	0	palladium coordination entity	catalyst
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.	2.08	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	5.21	3	1	delta-lactone; pyranoindolizinoquinoline; quinoline alkaloid; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor; genotoxin; plant metabolite
ferric chloride ferric chloride: RN given refers to cpd with MF of Fe-Cl3; used to induce experimental arterial thrombosis to evaluate antithrombotic agents	2.07	1	0	iron coordination entity	astringent; Lewis acid
phosphine phosphane : The simplest phosphine, consisting of a single phosphorus atom with three hydrogens attached.. phosphine : Phosphane (PH3) and compounds derived from it by substituting one, two or three hydrogen atoms by hydrocarbyl groups: RPH2, R2PH, R3P (R =/= H) are called primary, secondary and tertiary phosphines, respectively. A specific phosphine is preferably named as a substituted phosphane.	3.85	11	0	mononuclear parent hydride; phosphanes; phosphine	carcinogenic agent; fumigant insecticide
isopentenyladenosine Isopentenyladenosine: N(6)-[delta(3)-isopentenyl]adenosine. Isopentenyl derivative of adenosine which is a member of the cytokinin family of plant growth regulators.. N(6)-(Delta(2)-isopentenyl)adenosine : A nucleoside analogue in which adenosine has been modified by substitution at the 6-amino nitrogen by a Delta(2)-isopentenyl group.	3.87	11	0	N-ribosyl-N(6)-isopentenyladenine; nucleoside analogue	antineoplastic agent; plant growth regulator; plant metabolite
bromine Bromine: A halogen with the atomic symbol Br, atomic number 35, and atomic weight 79.904. It is a volatile reddish-brown liquid that gives off suffocating vapors, is corrosive to the skin, and may cause severe gastroenteritis if ingested.	4.3	6	0	diatomic bromine
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.	2.44	2	0	calcium phosphate
chromates Chromates: Salts of chromic acid containing the CrO(2-)4 radical.. chromate(2-) : A chromium oxoanion resulting from the removal of two protons from chromic acid.	1.94	1	0	chromium oxoanion; divalent inorganic anion	oxidising agent
copper sulfate Copper Sulfate: A sulfate salt of copper. It is a potent emetic and is used as an antidote for poisoning by phosphorus. It also can be used to prevent the growth of algae.. copper(II) sulfate : A metal sulfate compound having copper(2+) as the metal ion.	3.65	9	0	metal sulfate	emetic; fertilizer; sensitiser
silver nitrate Silver Nitrate: A silver salt with powerful germicidal activity. It has been used topically to prevent OPHTHALMIA NEONATORUM.	3.27	6	0	inorganic nitrate salt; silver salt	astringent
potassium sulfate potassium sulfate: RN given refers to cpd with MF of K2-H2SO4	2.52	2	0	inorganic potassium salt; potassium salt
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	4.33	20	0	dihydrogen
fluorine Fluorine: A nonmetallic, diatomic gas that is a trace element and member of the halogen family. It is used in dentistry as fluoride (FLUORIDES) to prevent dental caries.	5.28	17	0	diatomic fluorine; gas molecular entity	NMR chemical shift reference compound
chlorine Chlorine: An element with atomic symbol Cl, atomic number 17, and atomic weight 35, and member of the halogen family.	2.89	4	0	diatomic chlorine; gas molecular entity	bleaching agent
silver perchlorate [no description available]	2	1	0
deuterium oxide Deuterium Oxide: The isotopic compound of hydrogen of mass 2 (deuterium) with oxygen. (From Grant & Hackh's Chemical Dictionary, 5th ed) It is used to study mechanisms and rates of chemical or nuclear reactions, as well as biological processes.	1.98	1	0	deuterated compound; water	NMR solvent
chlorosulfonic acid [no description available]	2	1	0
galactose aldohexose : A hexose with a (potential) aldehyde group at one end.	2.91	4	0
sodium hydride [no description available]	2.05	1	0
sulfur monochloride [no description available]	2	1	0
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.	9.08	44	1	elemental molecule; gas molecular entity; reactive oxygen species; triatomic oxygen	antiseptic drug; disinfectant; electrophilic reagent; greenhouse gas; mutagen; oxidising agent; tracer
sodium selenite disodium selenite : An inorganic sodium salt composed of sodium and selenite ions in a 2:1 ratio.	2.41	2	0	inorganic sodium salt; selenite salt	nutraceutical
cadmium chloride Cadmium Chloride: A cadmium halide in the form of colorless crystals, soluble in water, methanol, and ethanol. It is used in photography, in dyeing, and calico printing, and as a solution to precipitate sulfides. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). cadmium dichloride : A cadmium coordination entity in which cadmium(2+) and Cl(-) ions are present in the ratio 2:1. Although considered to be ionic, it has considerable covalent character to its bonding.	2.41	2	0	cadmium coordination entity
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.	3.86	12	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
trolamine salicylate Arthritis: Acute or chronic inflammation of JOINTS.	2.87	4	0
carbendazim carbendazim: carcinogen when combined with sodium nitrite; principle metabolite of thiophanate methyl & benomyl; structure. carbendazim : A member of the class of benzimidazoles that is 2-aminobenzimidazole in which the primary amino group is substituted by a methoxycarbonyl group. A fungicide, carbendazim controls Ascomycetes, Fungi Imperfecti, and Basidiomycetes on a wide variety of crops, including bananas, cereals, cotton, fruits, grapes, mushrooms, ornamentals, peanuts, sugarbeet, soybeans, tobacco, and vegetables.	2.17	1	0	benzimidazole fungicide; benzimidazoles; benzimidazolylcarbamate fungicide; carbamate ester	antifungal agrochemical; antinematodal drug; metabolite; microtubule-destabilising agent
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.	4.62	27	0	ammonium salt; inorganic chloride	ferroptosis inhibitor
ethionine L-ethionine : An S-ethylhomocysteine that has S-configuration at the chiral centre.	1.94	1	0	S-ethylhomocysteine	antimetabolite; carcinogenic agent
titanium dioxide titanium dioxide: used medically as protectant against externally caused irritation & sunlight; high concentrations of dust may cause irritation to respiratory tract; RN given refers to titanium oxide (TiO2); structure. titanium dioxide : A titanium oxide with the formula TiO2. A naturally occurring oxide sourced from ilmenite, rutile and anatase, it has a wide range of applications.	2.76	3	0	titanium oxides	food colouring
3-carene 3-carene: RN given refers to cpd without isomeric designation	2.05	1	0	monoterpene
menthone menthone : The trans-stereoisomer of p-menthan-3-one.. (-)-menthone : A menthone that is cyclohexanone substituted by a methyl and an isopropyl group at positions 5 and 2 respectively (the 2S,5R-stereoisomer).	2.04	1	0	menthone
tiletamine hydrochloride Cyclohexanones: Cyclohexane ring substituted by one or more ketones in any position.. cyclohexanones : Any alicyclic ketone based on a cyclohexane skeleton and its substituted derivatives thereof.	4.55	24	0
levamisole Levamisole: An antihelminthic drug that has been tried experimentally in rheumatic disorders where it apparently restores the immune response by increasing macrophage chemotaxis and T-lymphocyte function. Paradoxically, this immune enhancement appears to be beneficial in rheumatoid arthritis where dermatitis, leukopenia, and thrombocytopenia, and nausea and vomiting have been reported as side effects. (From Smith and Reynard, Textbook of Pharmacology, 1991, p435-6). levamisole : A 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole that has S configuration. It is used (generally as the monohydrochloride salt) to treat parasitic worm infections in pigs, sheep and cattle and was formerly used in humans as an adjuvant to chemotherapy for the treatment of various cancers. It is also widely used as an adulterant to coccaine.	1.95	1	0	6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole	antinematodal drug; antirheumatic drug; EC 3.1.3.1 (alkaline phosphatase) inhibitor; immunological adjuvant; immunomodulator
clobutinol clobutinol: was minor as SILOMAT mapped to AMINO ALCOHOLS (63-79)	2.46	2	0	benzenes; organic amino compound
devrinol devrinol: structure. napropamide : A racemate composed of equimolar amounts of (S)- and (R)-napropamide.. N,N-diethyl-2-(naphthalen-1-yloxy)propanamide : A monocarboxylic acid amide that is propanamide substituted by two ethyl groups at the nitrogen atom and a naphthalen-1-yloxy group at position 2.	2.31	1	0	aromatic ether; monocarboxylic acid amide; naphthalenes
cromolyn sodium Cromolyn Sodium: A chromone complex that acts by inhibiting the release of chemical mediators from sensitized MAST CELLS. It is used in the prophylactic treatment of both allergic and exercise-induced asthma, but does not affect an established asthmatic attack.. disodium cromoglycate : An organic sodium salt that is the disodium salt of cromoglycic acid.	1.96	1	0	organic sodium salt	anti-asthmatic drug; drug allergen
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.	4.39	21	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
ethephon (2-chloroethyl)phosphonic acid: structure in first source. (2-chloroethyl)phosphonic acid : A phosphonic acid compound having a 2-chloroethyl substituent attached to the P-atom.	5.46	60	0	phosphonic acids	plant growth regulator
sodium bisulfide sodium bisulfide: RN given refers to sodium sulfide (Na(SH)); see also record for sodium sulfide (Na2S)	2.15	1	0
fluoroboric acid [no description available]	2.01	1	0	boron fluoride
fluorides [no description available]	4.51	24	0	halide anion; monoatomic fluorine
ochracin ochracin: produced by Aspergillus alutaceus; structure in first source	2.48	2	0	isochromanes
tomatine alpha-tomatine: in tomato fruits and vegetative plant tissues; structure in first source	2.25	1	0	alkaloid antibiotic; glycoalkaloid; glycoside; steroid alkaloid; tetrasaccharide derivative	antifungal agent; immunological adjuvant; phytotoxin
cresyl violet cresyl violet: RN given refers to chloride. cresyl violet : A cationic heterotetracyclic fluorescent dye derived from benzo[a]phenoxazine.	2	1	0
chromium chromium hexavalent ion: a human respiratory carcinogen	2.31	1	0	chromium cation; monoatomic hexacation
oryzalin oryzalin: a dinitroaniline; preemergence herbicide; structure. oryzalin : A sulfonamide that is benzenesulfonamide substituted at positions 3 and 5 by nitro groups and at position 4 by a dipropylamino group.	2.43	2	0	aromatic amine; C-nitro compound; sulfonamide; tertiary amino compound	agrochemical; antimitotic; herbicide
1-deoxynojirimycin 1-deoxy-nojirimycin: structure in first source. duvoglustat : An optically active form of 2-(hydroxymethyl)piperidine-3,4,5-triol having 2R,3R,4R,5S-configuration.	4.79	10	0	2-(hydroxymethyl)piperidine-3,4,5-triol; piperidine alkaloid	anti-HIV agent; anti-obesity agent; bacterial metabolite; EC 3.2.1.20 (alpha-glucosidase) inhibitor; hepatoprotective agent; hypoglycemic agent; plant metabolite
iodine [no description available]	3.5	8	0	halide anion; monoatomic iodine	human metabolite
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.	2.39	2	0	aminoglycoside antibiotic; anthracycline; p-quinones; tetracenequinones	antineoplastic agent; bacterial metabolite
phosphotyrosine Phosphotyrosine: An amino acid that occurs in endogenous proteins. Tyrosine phosphorylation and dephosphorylation plays a role in cellular signal transduction and possibly in cell growth control and carcinogenesis.. O(4)-phospho-L-tyrosine : A non-proteinogenic L-alpha-amino acid that is L-tyrosine phosphorylated at the phenolic hydroxy group.	1.99	1	0	L-tyrosine derivative; non-proteinogenic L-alpha-amino acid; O(4)-phosphotyrosine	Escherichia coli metabolite; immunogen
bromocriptine Bromocriptine: A semisynthetic ergotamine alkaloid that is a dopamine D2 agonist. It suppresses prolactin secretion.	2.15	1	0	indole alkaloid	antidyskinesia agent; antiparkinson drug; dopamine agonist; hormone antagonist
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.	17.34	1,757	5	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.	2.1	1	0	chloride salt; organic chloride salt	antiseptic drug; surfactant
4-anisaldehyde 4-anisaldehyde: RN given refers to cpd with specified locants for methoxy moieties; structure in Merck, 9th ed, #696. p-methoxybenzaldehyde : A member of the class of benzaldehydes consisting of benzaldehyde itself carrying a methoxy substituent at position 4.	2.05	1	0	benzaldehydes	bacterial metabolite; human urinary metabolite; insect repellent; plant metabolite
2,5-dimethylpyrazine [no description available]	2.15	1	0	pyrazines
myrcene myrcene: structure in first source. beta-myrcene : A monoterpene that is octa-1,6-diene bearing methylene and methyl substituents at positions 3 and 7 respectively.	2.45	2	0	monoterpene	anabolic agent; anti-inflammatory agent; flavouring agent; fragrance; plant metabolite; volatile oil component
pyrrolidine [no description available]	3.17	5	0	azacycloalkane; pyrrolidines; saturated organic heteromonocyclic parent
nonanal nonanal : A saturated fatty aldehyde formally arising from reduction of the carboxy group of nonanoic acid. Metabolite observed in cancer metabolism.	2.45	2	0	medium-chain fatty aldehyde; n-alkanal; saturated fatty aldehyde	human metabolite; plant metabolite
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.	3.34	1	1	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
sucrose octaacetate sucrose octaacetate: bitter tasting cpd preferred by rats to quinine; RN given refers to ((beta-D)-fructofuranosyl)-isomer	1.98	1	0	glycoside
tetrachloroethylene Tetrachloroethylene: A chlorinated hydrocarbon used as an industrial solvent and cooling liquid in electrical transformers. It is a potential carcinogen.	2.04	1	0	chlorocarbon; chloroethenes	nephrotoxic agent
ursodeoxycholic acid Ursodeoxycholic Acid: An epimer of chenodeoxycholic acid. It is a mammalian bile acid found first in the bear and is apparently either a precursor or a product of chenodeoxycholate. Its administration changes the composition of bile and may dissolve gallstones. It is used as a cholagogue and choleretic.. ursodeoxycholic acid : A bile acid found in the bile of bears (Ursidae) as a conjugate with taurine. Used therapeutically, it prevents the synthesis and absorption of cholesterol and can lead to the dissolution of gallstones.. ursodeoxycholate : A bile acid anion that is the conjugate base of ursodeoxycholic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.	2.08	1	0	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
pyrene pyrene: structure in Merck Index, 9th ed, #7746. pyrene : An ortho- and peri-fused polycyclic arene consisting of four fused benzene rings, resulting in a flat aromatic system.	2.75	3	0	ortho- and peri-fused polycyclic arene	fluorescent probe; persistent organic pollutant
4-methoxyamphetamine 4-methoxyamphetamine: para-methoxy derivative to amphetamine with hallucinogenic properties; minor descriptor (75-86); on line & INDEX MEDICUS search AMPHETAMINES (75-86); RN given refers to parent compound without isomeric designation	4.9	1	1
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.	3.08	5	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.	4.28	19	0
alkenes [no description available]	13.46	137	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.	11.73	43	0	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
azoxymethane Azoxymethane: A potent carcinogen and neurotoxic compound. It is particularly effective in inducing colon carcinomas.	2.42	2	0
sodium azide Sodium Azide: A cytochrome oxidase inhibitor which is a nitridizing agent and an inhibitor of terminal oxidation. (From Merck Index, 12th ed). sodium azide : The sodium salt of hydrogen azide (hydrazoic acid).	3.11	5	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.	4.32	19	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.	3.6	9	0	ADP-sugar	Escherichia coli metabolite; mouse metabolite
tramadol Tramadol: A narcotic analgesic proposed for severe pain. It may be habituating.. tramadol : A racemate consisting of equal amounts of (R,R)- and (S,S)-tramadol. A centrally acting synthetic opioid analgesic, used (as the hydrochloride salt) to treat moderately severe pain. The (R,R)-enantiomer exhibits ten-fold higher analgesic potency than the (S,S)-enantiomer. Originally developed by Gruenenthal GmbH and launched in 1977, it was subsequently isolated from the root bark of the South African tree Nauclea latifolia.. (R,R)-tramadol : A 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol in which both stereocentres have R-configuration; the (R,R)-enantiomer of the racemic opioid analgesic tramadol, it exhibits ten-fold higher analgesic potency than the (S,S)-enantiomer.	4.9	1	1	2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol	adrenergic uptake inhibitor; antitussive; capsaicin receptor antagonist; delta-opioid receptor agonist; kappa-opioid receptor agonist; metabolite; mu-opioid receptor agonist; muscarinic antagonist; nicotinic antagonist; NMDA receptor antagonist; opioid analgesic; serotonergic antagonist; serotonin uptake inhibitor
cyclopenta(c,d)pyrene cyclopenta(c,d)pyrene: structure	3.21	6	0	pyrenes
norflurazone norflurazone: structure. norflurazon : A pyridazinone that is pyridazin-3(2H)-one which is substituted at positions 2, 4, and 5 by m-(trifluoromethyl)phenyl, chloro, and methylamino groups, respectively. A pre-emergence herbicide used to control grasses and broad-leafed weeds in a variety of crops. Not approved for use within the European Union.	2.48	2	0	(trifluoromethyl)benzenes; organochlorine compound; pyridazinone; secondary amino compound	agrochemical; carotenoid biosynthesis inhibitor; herbicide
vanadyl sulfate [no description available]	2.03	1	0	metal sulfate; vanadium coordination entity
oxovanadium iv oxovanadium IV: forms complexes with simple sugars	2.03	1	0	vanadium oxide
nicergoline Nicergoline: An ergot derivative that has been used as a cerebral vasodilator and in peripheral vascular disease. It may ameliorate cognitive deficits in CEREBROVASCULAR DISORDERS.	2.08	1	0	organic heterotetracyclic compound; organonitrogen heterocyclic compound
gallium citrate [no description available]	4.9	1	1
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.	3.1	5	0	polycyclic ether	antibacterial agent; antimicrobial agent; bacterial metabolite; potassium ionophore
1-(9-fluorenyl)methyl chloroformate 1-(9-fluorenyl)methyl chloroformate: used for tagging silica-based derivatization reagents in HPLC	2.1	1	0
zidovudine Zidovudine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.. zidovudine : A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.	2.39	2	0	azide; pyrimidine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; HIV-1 reverse transcriptase inhibitor
acetylgalactosamine Acetylgalactosamine: The N-acetyl derivative of galactosamine.	2.68	3	0	N-acetyl-D-hexosamine; N-acetylgalactosamine	Escherichia coli metabolite; human metabolite; mouse metabolite
3,4,3',4'-tetrachlorobiphenyl 3,4,3',4'-tetrachlorobiphenyl: RN given refers to parent cpd. 3,3',4,4'-tetrachlorobiphenyl : A tetrachlorobiphenyl that is biphenyl in which the hydrogens at position 3 and 4 on each phenyl group are replaced by chlorines.	2.06	1	0	dichlorobenzene; tetrachlorobiphenyl
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).	8.8	61	1	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
2,3,4,5-tetrachlorobiphenyl tetrachlorobiphenyl : Any polychlorobiphenyl with molecular formula C12H6Cl4.	2.04	1	0	tetrachlorobenzene; tetrachlorobiphenyl
etoposide [no description available]	2.7	3	0	beta-D-glucoside; furonaphthodioxole; organic heterotetracyclic compound	antineoplastic agent; DNA synthesis inhibitor
substance p [no description available]	7.01	1	0	peptide	neurokinin-1 receptor agonist; neurotransmitter; vasodilator agent
isoproturon isoproturon : A member of the class of phenylureas that is 1,1-dimethylurea substituted by a p-cumenyl group at position 3. A selective, systemic herbicide used to control annual grasses and broadleaf weeds in cereals, its use within the EU has been banned after September 2017 on the grounds of potential groundwater contamination and risks to aquatic life; there have also been concerns about its endocrine-disrupting properties.	2.17	1	0	3-(3,4-substituted-phenyl)-1,1-dimethylurea	agrochemical; environmental contaminant; herbicide; xenobiotic
2,5-dichlorobiphenyl 2,5-dichlorobiphenyl : A dichlorobiphenyl that is p-dichlorobenzene in which one of the hydrogens has been replaced by a phenyl group.	2.04	1	0	dichlorobenzene; dichlorobiphenyl
2,4'-dichlorobiphenyl 2,4'-dichlorobiphenyl: RN given refers to unlabeled cpd. 2,4'-dichlorobiphenyl : A dichlorobiphenyl that is chlorobenzene in which the hydrogen at position 2 has been replaced by a 4-chlorophenyl group.	2.04	1	0	dichlorobiphenyl; monochlorobenzenes
2,4,6-trichlorobiphenyl 2,4,6-trichlorobiphenyl: structure given in first source	2.04	1	0
ribavirin Rebetron: Rebetron is tradename	9.36	6	0	1-ribosyltriazole; aromatic amide; monocarboxylic acid amide; primary carboxamide	anticoronaviral agent; antiinfective agent; antimetabolite; antiviral agent; EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
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.	2.91	4	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.	1.95	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]	1.99	1	0	aromatic ether; monocarboxylic acid amide; monocarboxylic acid; monochlorobenzenes	antilipemic drug; environmental contaminant; geroprotector; xenobiotic
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.	2.06	1	0	5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate	antihypertensive agent; calcium channel blocker; vasodilator agent
oxyfluorofen oxyfluorofen: structure	2.01	1	0	aromatic ether	EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor; herbicide
ng-nitroarginine methyl ester NG-Nitroarginine Methyl Ester: A non-selective inhibitor of nitric oxide synthase. It has been used experimentally to induce hypertension.	2.53	2	0	alpha-amino acid ester; L-arginine derivative; methyl ester; N-nitro compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor
deoxynivalenol deoxynivalenol : A trichothecene mycotoxin produced by Fusarium to which wheat, barley, maize (corn) and their products are susceptible to contamination.	3.06	4	0	cyclic ketone; enone; primary alcohol; secondary alpha-hydroxy ketone; trichothecene; triol	mycotoxin
quisqualic acid Quisqualic Acid: An agonist at two subsets of excitatory amino acid receptors, ionotropic receptors that directly control membrane channels and metabotropic receptors that indirectly mediate calcium mobilization from intracellular stores. The compound is obtained from the seeds and fruit of Quisqualis chinensis.	2.9	4	0	non-proteinogenic alpha-amino acid
desflurane Desflurane: A fluorinated ether that is used as a volatile anesthetic for maintenance of general anesthesia.	1.99	1	0	organofluorine compound	inhalation anaesthetic
indacrinone indacrinone: polyvalent saluretic; RN given refers to parent cpd without isomeric designation; structure	2.71	3	0
metalaxyl metalaxyl: RN given refers to (DL-Ala)-isomer. metalaxyl : A racemate comprising equal amounts of (R)- and (S)-metalaxyl. A systemic fungicide, it is active against phytopathogens of the order Peronosporales and is used to conrtrol Pythium in a number of vegetable crops.. methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate : An alanine derivative that is methyl alaninate in which one of the hydrogens attached to the nitrogen is substituted by a methoxyacetyl group, while the other is substituted by a 2,6-dimethylphenyl group.	2.31	1	0	alanine derivative; aromatic amide; carboxamide; ether; methyl ester
enkephalin, methionine Enkephalin, Methionine: One of the endogenous pentapeptides with morphine-like activity. It differs from LEU-ENKEPHALIN by the amino acid METHIONINE in position 5. Its first four amino acid sequence is identical to the tetrapeptide sequence at the N-terminal of BETA-ENDORPHIN.	1.98	1	0
fluridone [no description available]	3	4	0	phenylpyridine	carotenoid biosynthesis inhibitor
propiconazole Orbit: Bony cavity that holds the eyeball and its associated tissues and appendages.	1.95	1	0	conazole fungicide; cyclic ketal; dichlorobenzene; triazole fungicide; triazoles	antifungal agrochemical; EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor; environmental contaminant; xenobiotic
n'-cyano-n-(3-pyridyl)-n''-(t-butyl)guanidine N'-cyano-N-(3-pyridyl)-N''-(t-butyl)guanidine: structure given in first source	2.43	2	0
acifluorfen [no description available]	2.01	1	0	aromatic ether; benzoic acids; C-nitro compound; monocarboxylic acid; organochlorine compound; organofluorine compound	agrochemical; EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor; herbicide
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.	3.75	3	0	alkanethiol; L-proline derivative; N-acylpyrrolidine; pyrrolidinemonocarboxylic acid	antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor
oltipraz oltipraz : A 1,2-dithiole that is 3H-1,2-dithiole-3-thione substituted at positions 4 and 5 by methyl and pyrazin-2-yl groups respectively.	1.99	1	0	1,2-dithiole; pyrazines	angiogenesis modulating agent; antimutagen; antineoplastic agent; antioxidant; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; neurotoxin; protective agent; schistosomicide drug
nicorandil Nicorandil: A derivative of the NIACINAMIDE that is structurally combined with an organic nitrate. It is a potassium-channel opener that causes vasodilatation of arterioles and large coronary arteries. Its nitrate-like properties produce venous vasodilation through stimulation of guanylate cyclase.. nicorandil : A pyrimidinecarboxamide that is nicotinamide in which one of the hydrogens attached to the carboxamide nitrogen is replaced by a 2-(nitrooxy)ethyl group. It has both nitrate-like and ATP-sensitive potassium channel activator properties, and is used for the prevention and treatment of angina pectoris.	2	1	0	nitrate ester; pyridinecarboxamide	potassium channel opener; vasodilator agent
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.	4.19	17	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
fomesafen fomesafen: a protoporphyrinogen oxidase-inhibiting herbicide. fomesafen : An N-sulfonylcarboxamide that is N-(methylsulfonyl)benzamide in which the phenyl ring is substituted by a nitro group at position 2 and a 2-chloro-4-(trifluoromethyl)phenoxy group at position 5. A protoporphyrinogen oxidase inhibitor, it was specially developed for use (generally as the corresponding sodium salt, fomesafen-sodium) for post-emergence control of broad-leaf weeds in soya.	3.2	6	0	aromatic ether; C-nitro compound; monochlorobenzenes; N-sulfonylcarboxamide; organofluorine compound; phenols	agrochemical; EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor; herbicide
swainsonine Swainsonine: An indolizidine alkaloid from the plant Swainsona canescens that is a potent alpha-mannosidase inhibitor. Swainsonine also exhibits antimetastatic, antiproliferative, and immunomodulatory activity.. swainsonine : An indolizidine alkaloid isolated from the plant Swainsona canescens with three hydroxy substituents at positions 1, 2 and 8.	4.69	9	0	indolizidine alkaloid	antineoplastic agent; EC 3.2.1.114 (mannosyl-oligosaccharide 1,3-1,6-alpha-mannosidase) inhibitor; immunological adjuvant; plant metabolite
2,2-dimethyl-4-(chloromethyl)-1,3-dioxa-2-silacyclopentane [no description available]	2.88	4	0
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).	3.4	7	0	delta-lactone; fatty acid ester; hexahydronaphthalenes; polyketide; statin (naturally occurring)	anticholesteremic drug; antineoplastic agent; Aspergillus metabolite; prodrug
flupirtine flupirtine: RN given refers to parent cpd without isomeric designation	3.43	1	1	aminopyridine
rimcazole rimcazole: RN given refers to (cis)-isomer; structure given in first source	1.99	1	0	carbazoles
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).	3.99	4	0	indolizidine alkaloid	anti-HIV-1 agent; anti-inflammatory agent; EC 3.2.1.* (glycosidase) inhibitor; metabolite
idazoxan Idazoxan: A benzodioxane-linked imidazole that has alpha-2 adrenoceptor antagonist activity.. idazoxan : A benzodioxine that is 2,3-dihydro-1,4-benzodioxine in which one of the hydrogens at position 2 has been replaced by a 4,5-dihydro-1H-imidazol-2-yl group.	2.05	1	0	benzodioxine; imidazolines	alpha-adrenergic antagonist
clomazone clomazone: an herbicide. clomazone : An isoxazolidinone that is 1,2-oxazolidin-3-one substituted by a 2-chlorobenzyl group at position 2 and two methyl groups at position 4.	2.08	1	0	isoxazolidinone; monochlorobenzenes	agrochemical; carotenoid biosynthesis inhibitor; environmental contaminant; herbicide; xenobiotic
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.	5.73	2	2	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
cilazapril, anhydrous Cilazapril: One of the ANGIOTENSIN-CONVERTING ENZYME INHIBITORS (ACE inhibitors) used for hypertension. It is a prodrug that is hydrolyzed after absorption to its main metabolite cilazaprilat.. cilazapril : A pyridazinodiazepine resulting from the formal condensation of the carboxy group of cilazaprilat with ethanol. It is a drug used in the treatment of hypertension and heart failure.	3.06	1	0	dicarboxylic acid monoester; ethyl ester; pyridazinodiazepine	antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; prodrug
fura-2 Fura-2: A fluorescent calcium chelating agent which is used to study intracellular calcium in tissues.	1.97	1	0
finasteride Finasteride: An orally active 3-OXO-5-ALPHA-STEROID 4-DEHYDROGENASE inhibitor. It is used as a surgical alternative for treatment of benign PROSTATIC HYPERPLASIA.. finasteride : An aza-steroid that is a synthetic drug for the treatment of benign prostatic hyperplasia.	2.15	1	0	3-oxo steroid; aza-steroid; delta-lactam	androgen antagonist; antihyperplasia drug; EC 1.3.1.22 [3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+))] inhibitor
bimakalim bimakalim: potassium channel activator	1.98	1	0
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.	2.6	1	0	pyranoindolizinoquinoline	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor
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.	2.15	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
aripiprazole Aripiprazole: A piperazine and quinolone derivative that is used primarily as an antipsychotic agent. It is a partial agonist of SEROTONIN RECEPTOR, 5-HT1A and DOPAMINE D2 RECEPTORS, where it also functions as a post-synaptic antagonist, and an antagonist of SEROTONIN RECEPTOR, 5-HT2A. It is used for the treatment of SCHIZOPHRENIA and BIPOLAR DISORDER, and as an adjunct therapy for the treatment of depression.. aripiprazole : An N-arylpiperazine that is piperazine substituted by a 4-[(2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)oxy]butyl group at position 1 and by a 2,3-dichlorophenyl group at position 4. It is an antipsychotic drug used for the treatment of Schizophrenia, and other mood disorders.	3.59	2	0	aromatic ether; delta-lactam; dichlorobenzene; N-alkylpiperazine; N-arylpiperazine; quinolone	drug metabolite; H1-receptor antagonist; second generation antipsychotic; serotonergic agonist
lamivudine [no description available]	4.98	2	1	monothioacetal; nucleoside analogue; oxacycle; primary alcohol	allergen; anti-HBV agent; antiviral drug; EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor; HIV-1 reverse transcriptase inhibitor; prodrug
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.	2.04	1	0	1,2-benzisothiazole; indolones; organochlorine compound; piperazines	antipsychotic agent; dopaminergic antagonist; histamine antagonist; muscarinic antagonist; psychotropic drug; serotonergic antagonist
zanamivir Zanamivir: A guanido-neuraminic acid that is used to inhibit NEURAMINIDASE.	16.74	89	4	guanidines	antiviral agent; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor
emtricitabine Emtricitabine: A deoxycytidine analog and REVERSE TRANSCRIPTASE INHIBITOR with antiviral activity against HIV-1 and HEPATITIS B viruses. It is used to treat HIV INFECTIONS.. emtricitabine : An organofluorine compound that is 5-fluorocytosine substituted at the 1 position by a 2-(hydroxymethyl)-1,3-oxathiolan-5-yl group (2R,5S configuration). It is used in combination therapy for the treatment of HIV-1 infection.	4.9	1	1	monothioacetal; nucleoside analogue; organofluorine compound; pyrimidone	antiviral drug; HIV-1 reverse transcriptase inhibitor
adenosine quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit	6.02	36	0	adenosines; purines D-ribonucleoside	analgesic; anti-arrhythmia drug; fundamental metabolite; human metabolite; vasodilator agent
n-butyllithium [no description available]	2.55	2	0
myrtenal myrtenal: RN refers to cpd without isomeric designation; structure given in first source	2.17	1	0
3-methyl-1,2-cyclopentanedione 3-methyl-1,2-cyclopentanedione: a peroxynitrite scavenger isolated from coffee extract; structure in first source	2.94	4	0	cyclic ketone
amyl nitrate [no description available]	2.02	1	0
gadolinium chloride gadolinium chloride: a macrophage inhibitor; reduces pulmonary injury and inflammatory mediator production induced by inhaled ozone	2.46	2	0	gadolinium coordination entity	TRP channel blocker
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.	2.96	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
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.	1.99	1	0	aminoacridines; aromatic amine; tertiary amino compound	fluorochrome; histological dye
2-methyl-5-(1-methylethyl)bicyclo(3.1.0)hexan-2-ol 2-methyl-5-(1-methylethyl)bicyclo(3.1.0)hexan-2-ol: fragrance ingredient; structure in first source	2.21	1	0	p-menthane monoterpenoid
ketoisophorone ketoisophorone: structure in first source	2.06	1	0	cyclohexenones
benzylaminopurine benzylaminopurine: a plant growth regulator. N-benzyladenine : A member of the class of 6-aminopurines that is adenine in which one of the hydrogens of the amino group is replaced by a benzyl group.	3.77	10	0	6-aminopurines	cytokinin; plant metabolite
trifluoromethanesulfonic acid trifluoromethanesulfonic acid: deblocking reagent for peptide synthesis; RN given refers to parent cpd. triflic acid : A one-carbon compound that is methanesulfonic acid in which the hydrogens attached to the methyl carbon have been replaced by fluorines.	2.74	3	0	one-carbon compound; perfluoroalkanesulfonic acid
isothiocyanic acid [no description available]	2.03	1	0	hydracid; one-carbon compound
cuprous chloride cuprous chloride: RN given refers to unlabeled cpd. copper(I) chloride : An inorganic chloride of copper in which the metal is in the +1 oxidation state.	2.04	1	0	copper molecular entity; inorganic chloride	agrochemical; molluscicide
2-butene 2-butene: RN given refers to cpd without isomeric designation	2.15	1	0	but-2-ene
4,5-dimethyl-3-hydroxy-2(5h)-furanone [no description available]	2.03	1	0	butenolide	metabolite
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.	1.99	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.	5.98	96	0	hydrochloride	adrenergic antagonist; antidepressant; H1-receptor antagonist; sedative; serotonin uptake inhibitor
efavirenz efavirenz: HIV-1 reverse transcriptase inhibitor. efavirenz : 1,4-Dihydro-2H-3,1-benzoxazin-2-one substituted at the 4 position by cyclopropylethynyl and trifluoromethyl groups (S configuration) and at the 6 position by chlorine. A non-nucleoside reverse transcriptase inhibitor with activity against HIV, it is used with other antiretrovirals for combination therapy of HIV infection.	4.9	1	1	acetylenic compound; benzoxazine; cyclopropanes; organochlorine compound; organofluorine compound	antiviral drug; HIV-1 reverse transcriptase inhibitor
adamantanine adamantanine: inhibitor of amino acid transport; RN given refers to parent cpd	2.03	1	0
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.	7.87	94	0	D-glucopyranose	epitope; mouse metabolite
mevastatin mevastatin: antifungal metabolite from Penicillium brevicopactum; potent inhibitory activity to sterol synthesis; structure. mevastatin : A carboxylic ester that is pravastatin that is lacking the allylic hydroxy group. A hydroxymethylglutaryl-CoA reductase inhibitor (statin) isolated from Penicillium citrinum and from Penicillium brevicompactum, its clinical use as a lipid-regulating drug ceased following reports of toxicity in animals.	1.97	1	0	2-pyranones; carboxylic ester; hexahydronaphthalenes; polyketide; statin (naturally occurring)	antifungal agent; apoptosis inducer; EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor; fungal metabolite; Penicillium metabolite
l 154819 mevinolinic acid: RN given refers to parent cpd; structure given in first source. mevinolinic acid : A polyketide obtained by hydrolysis of the pyranone ring of lovastatin.	2.13	1	0	carbobicyclic compound; dihydroxy monocarboxylic acid; fatty acid ester; polyketide	Aspergillus metabolite; drug metabolite; EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor; teratogenic agent
lanthanum chloride lanthanum chloride: RN given refers to parent cpd	2.95	4	0
ursolic acid [no description available]	2.13	1	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	geroprotector; plant metabolite
cyclen cyclen: macrocyclic polyamine metal-complexing agent. 1,4,7,10-tetraazacyclododecane : An azacycloalkane that is cyclododecane in which the carbon atoms at positions 1, 4, 7 and 10 are replaced by nitrogen atoms.	2.07	1	0	azacycloalkane; crown amine; saturated organic heteromonocyclic parent
thiazolyl blue thiazolyl blue: RN & II refers to bromide. 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide : The bromide salt of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium.	3.11	5	0	organic bromide salt	colorimetric reagent; dye
thymidine 5'-triphosphate thymidine 5'-triphosphate: RN given refers to parent cpd. dTTP : A thymidine phosphate having a triphosphate group at the 5'-position.	1.94	1	0	pyrimidine 2'-deoxyribonucleoside 5'-triphosphate; thymidine phosphate	Escherichia coli metabolite; mouse metabolite
betulinic acid [no description available]	3.16	4	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	anti-HIV agent; anti-inflammatory agent; antimalarial; antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; plant metabolite
baicalin [no description available]	2.07	1	0	dihydroxyflavone; glucosiduronic acid; glycosyloxyflavone; monosaccharide derivative	antiatherosclerotic agent; antibacterial agent; anticoronaviral agent; antineoplastic agent; antioxidant; cardioprotective agent; EC 2.7.7.48 (RNA-directed RNA polymerase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; ferroptosis inhibitor; neuroprotective agent; non-steroidal anti-inflammatory drug; plant metabolite; prodrug
oseltamivir Oseltamivir: An acetamido cyclohexene that is a structural homolog of SIALIC ACID and inhibits NEURAMINIDASE.. oseltamivir : A cyclohexenecarboxylate ester that is the ethyl ester of oseltamivir acid. An antiviral prodrug (it is hydrolysed to the active free carboxylic acid in the liver), it is used to slow the spread of influenza.	19.75	133	11	acetamides; amino acid ester; cyclohexenecarboxylate ester; primary amino compound	antiviral drug; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor; environmental contaminant; prodrug; xenobiotic
epigallocatechin gallate epigallocatechin gallate: a steroid 5alpha-reductase inhibitor and antimutagen in green tea (Camellia sinensis). (-)-epigallocatechin 3-gallate : A gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (-)-epigallocatechin.	2.11	1	0	flavans; gallate ester; polyphenol	antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite
gallocatechol gallocatechol: structure give in first source; RN given for (trans-(+-))-omer; inhibits DNA-dependent DNA & RNA polymerases. (+)-gallocatechin : A gallocatechin that has (2R,3S)-configuration. It is found in green tea and bananas.. gallocatechin : A catechin that is a flavan substituted by hydroxy groups at positions 3, 3', 4', 5, 5' and 7 (the trans isomer). It is isolated from Acacia mearnsii.	2.17	1	0	gallocatechin	antioxidant; metabolite; radical scavenger
25-hydroxycholesterol [no description available]	2.9	4	0	25-hydroxy steroid; oxysterol	human metabolite
1,2,4-triazole-3-carboxamide 1,2,4-triazole-3-carboxamide : A member of the class of triazoles that is 1H-1,2,4-triazole substituted by an aminocarbonyl group at position 3. It is the major catabolite and aglycon of ribavirin.	2.01	1	0	aromatic amide; monocarboxylic acid amide; primary carboxamide; triazoles	drug metabolite; human urinary metabolite
tris(2,2'-bipyridine)ruthenium(II) tris(2,2'-bipyridyl)ruthenium(II): a fluorescent dye; structure in first source	2.02	1	0	ruthenium coordination entity	fluorochrome
fluorophosphate fluorophosphate: inhibits Phosphorylas phosphatase irreversibly; RN given refers to parent cpd	1.92	1	0	fluorine molecular entity; phosphoric acid derivative
aristeromycin aristeromycin: RN given refers to (1R-(1alpha,2alpha,3beta,5alpha)-isomer	3.27	6	0
2-deoxy-2,3-dehydro-n-acetylneuraminic acid 2-deoxy-2,3-dehydro-N-acetylneuraminic acid: also known as NeuAc2en, but this is also synonym for another compound. 2-deoxy-2,3-dehydro-N-acetylneuraminic acid : N-Acetylneuraminic acid reduced across the 2,3-bond with loss of the hydroxy group at C-2; it is a minor component of body fluids although abundant in sialuria.	2.06	1	0	N-acetylneuraminic acids
glutathione disulfide Glutathione Disulfide: A GLUTATHIONE dimer formed by a disulfide bond between the cysteine sulfhydryl side chains during the course of being oxidized.	1.99	1	0	glutathione derivative; organic disulfide	Escherichia coli metabolite; mouse metabolite
baccatin iii [no description available]	3.41	7	0	acetate ester; benzoate ester; tetracyclic diterpenoid	plant metabolite
4-nitrobenzylthioinosine 4-nitrobenzylthioinosine: inhibitor of nucleoside transport; acts on ENT1	2.42	2	0	purine nucleoside
sinefungin [no description available]	2.03	1	0	adenosines; non-proteinogenic alpha-amino acid	antifungal agent; antimicrobial agent
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.	3.21	1	0	cephalosporin	fungal metabolite
dicarbine dicarbine: minor descriptor (77-84); on-line & Index Medicus search CARBOLINES (77-84); RN given refers to parent cpd without isomeric designation	2.1	1	0
glisentide glisentide: structure in first source	3.35	7	0	sulfonamide
n-acetylproline N-acetylproline: RN given refers to (DL)-isomer	1.97	1	0	L-proline derivative; N-acetyl-L-amino acid; N-acylpyrrolidine; pyrrolidinemonocarboxylic acid
salicylhydroxamic acid [no description available]	2.98	4	0	hydroxamic acid; phenols	antibacterial drug; EC 1.11.2.2 (myeloperoxidase) inhibitor; EC 3.5.1.5 (urease) inhibitor; trypanocidal drug
benzeneboronic acid [no description available]	2.45	2	0	boronic acids
estradiol-3,4-quinone estradiol-3,4-quinone: structure in first source	2.07	1	0
1,7-phenanthroline [no description available]	2.45	2	0	phenanthroline
pyrazolo(3,4-d)pyrimidine [no description available]	2.02	1	0
benzo-1,2,3-thiadiazole [no description available]	4.84	31	0
bicyclo(3.1.0)hexane [no description available]	3.5	2	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.	6.1	35	0	1,2,3-triazole
1h-tetrazole tetrazole : An azaarene that is a five-membered ring composed of 4 nitrogen and 1 carbon atom.. 2H-tetrazole : A tetrazole tautomer where the proton is located on the 2 position.	1.92	1	0	one-carbon compound; tetrazole
trifluoroacetamide [no description available]	2.04	1	0
tetraphenylcyclopentadienone tetraphenylcyclopentadienone: singlet oxygen trapping agent	2.98	4	0	stilbenoid
isocoumarins Isocoumarins: Compounds that differ from COUMARINS in having the positions of the ring and ketone oxygens reversed so the keto oxygen is at the 1-position of the molecule.. isocoumarin : The simplest member of the class of isocoumarins that is 1H-isochromene which is substituted by an oxo group at position 1.	2.8	3	0	isocoumarins
alpha-methylene gamma-butyrolactone alpha-methylene gamma-butyrolactone : A butan-4-olide having a methylene group at the 3-position.	2.4	2	0	butan-4-olide	anti-ulcer drug; gastrointestinal drug
fluorodeoxyglucose f18 Fluorodeoxyglucose F18: The compound is given by intravenous injection to do POSITRON-EMISSION TOMOGRAPHY for the assessment of cerebral and myocardial glucose metabolism in various physiological or pathological states including stroke and myocardial ischemia. It is also employed for the detection of malignant tumors including those of the brain, liver, and thyroid gland. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1162)	5.8	6	1	2-deoxy-2-((18)F)fluoro-D-glucose; 2-deoxy-2-fluoro-aldehydo-D-glucose
artemisinin (+)-artemisinin : A sesquiterpene lactone obtained from sweet wormwood, Artemisia annua, which is used as an antimalarial for the treatment of multi-drug resistant strains of falciparum malaria.	6.12	15	0	organic peroxide; sesquiterpene lactone	antimalarial; plant metabolite
1-triacontanol 1-triacontanol: constituent of Apocynum venetum leaf & Cirsium segetum. triacontan-1-ol : An ultra-long-chain primary fatty alcohol that is triacontane in which one of the terminal methyl hydrogens is replaced by a hydroxy group.	2.74	3	0	fatty alcohol 30:0; ultra-long-chain primary fatty alcohol
1,2,3,4-tetrahydroquinoline 1,2,3,4-tetrahydroquinoline: structure in first source. 1,2,3,4-tetrahydroquinoline : A member of the class of quinolines that is the 1,2,3,4-tetrahydro derivative of quinoline.	3	4	0	quinolines
phenylpropiolic acid phenylpropiolic acid: structure. phenylpropiolic acid : An acetylenic compound that is propynoic acid in which the acetylenic hydrogen is replaced by a phenyl group.	3.58	2	0	acetylenic compound; alpha,beta-unsaturated monocarboxylic acid; benzenes
ethyl 4-chloro-3-oxobutanoate [no description available]	2.07	1	0
fructose-6-phosphate fructose-6-phosphate: RN given refers to parent cpd with unspecified isomeric designation. fructose 6-phosphate : A ketohexose monophosphate consisting of fructose having a phosphate group located at the 6-position.	2.41	2	0	D-fructose 6-phosphate
benzocyclobutene benzocyclobutene : A carbobicyclic compound that is benzene fused to a cyclobutane ring.	7.03	1	0	carbobicyclic compound	metabolite
cyclopropylamine cyclopropylamine: RN given refers to parent cpd. cyclopropylamine : A primary aliphatic amine that consists of cyclopropane bearing a single amino substituent.	2.08	1	0	primary aliphatic amine	mouse metabolite
4-cyclopentene-1,3-dione 4-cyclopentene-1,3-dione: induces electrical excitability in crustacean muscle	3.4	7	0
n-methylmaleimide N-methylmaleimide: structure in first source	2.04	1	0
glutarimide [no description available]	2.04	1	0	dicarboximide; piperidones
8-azaadenine 8-azaadenine: xanthine oxidase inhibitor. 8-azaadenine : A triazolopyrimidine that is [1,2,3]triazolo[4,5-d]pyrimidine bearing an amino substituent at position 7.	1.99	1	0	aromatic amine; nucleobase analogue; triazolopyrimidines	EC 1.17.3.2 (xanthine oxidase) inhibitor; Mycoplasma genitalium metabolite
morpholinopropane sulfonic acid 3-(N-morpholino)propanesulfonic acid : A Good's buffer substance, pKa = 7.2 at 20 degreeC.	2	1	0	MOPS; morpholines; organosulfonic acid
acamprosate Acamprosate: Structural analog of taurine that is used for the prevention of relapse in individuals with ALCOHOLISM.. acamprosate : An organosulfonic acid that is propane-1-sulfonic acid substituted by an acetylamino group at position 3.	2.71	3	0	acetamides; organosulfonic acid	environmental contaminant; neurotransmitter agent; xenobiotic
n-methylscopolamine N-Methylscopolamine: A muscarinic antagonist used to study binding characteristics of muscarinic cholinergic receptors.	1.99	1	0
cromakalim Cromakalim: A potassium-channel opening vasodilator that has been investigated in the management of hypertension. It has also been tried in patients with asthma. (Martindale, The Extra Pharmacopoeia, 30th ed, p352)	3.25	6	0
atipamezole [no description available]	2.06	1	0
masoprocol Masoprocol: A potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. The compound also inhibits formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase to a lesser extent. It also serves as an antioxidant in fats and oils.. masoprocol : The meso-form of nordihydroguaiaretic acid. An antioxidant found in the creosote bush, Larrea divaricata, it is a potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. It also inhibits (though to a lesser extent) formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase.	3.12	5	0	nordihydroguaiaretic acid	antineoplastic agent; hypoglycemic agent; lipoxygenase inhibitor; metabolite
inproquone inproquone: major descriptor (78-80); replaced major descriptor Bayer E39 (63-77); on-line search AZIRINES (66-80); Index Medicus search Bayer E39 (63-77), INPROQUONE (78-80)	1.93	1	0
quindoxin quindoxin: RN given refers to parent cpd; structure in Negwer, 5th ed, #702	2.07	1	0	quinoxaline derivative
cyclarbamate cyclarbamate: structure	2.03	1	0	carbamate ester
ubenimex ubenimex: growth inhibitor	2.03	1	0
7-hydroxystaurosporine [no description available]	1.99	1	0
illimaquinone illimaquinone: structure given in first source; isolated from the Red Sea sponge Smenospongia; inhibits the RNase H. activity of HIV-1 reverse transcriptase	2.68	3	0	monohydroxy-1,4-benzoquinones; prenylquinone	metabolite
coptisine coptisine: RN given refers to parent cpd	2.1	1	0	alkaloid	metabolite
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.	2.61	2	0	diol; pentacyclic triterpenoid	analgesic; anti-inflammatory agent; antineoplastic agent; antiviral agent; metabolite
leupeptin [no description available]	3.49	8	0	aldehyde; tripeptide	bacterial metabolite; calpain inhibitor; cathepsin B inhibitor; EC 3.4.21.4 (trypsin) inhibitor; serine protease inhibitor
alkannin alkannin: a naphthazarin used to promote wound healing, from the plant Alkanna tinctoria; RN given refers to (S)-isomer; structure	2.41	1	0	hydroxy-1,4-naphthoquinone
5-methyl-1,10-phenanthroline [no description available]	2.08	1	0
neplanocin a neplanocin A: neplanocins are antitumor antibiotics & carbocyclic analogs of purine nucleosides from Ampullarilla regularis A11079; see also neplanocin B, neplanocin C, neplanocin D & neplanocin F; structure in first source; a potent inhibitor of S-adenosylhomocysteine hydrolase	8.28	6	0
serpentine (alkaloid) serpentine (alkaloid): do not confuse with mineral serpentine; RN given refers to (19alpha)-isomer; structure	2.17	1	0	carboxylic ester; iminium betaine; indole alkaloid; quinolizines; zwitterion
tosyllysine chloromethyl ketone Tosyllysine Chloromethyl Ketone: An inhibitor of SERINE ENDOPEPTIDASES. Acts as an alkylating agent and is known to interfere with the translation process.	2.39	2	0	sulfonic acid derivative
beta-amyrin beta-amyrin: alpha-amyrin is also available; a 5 ring triterpene derived from oleanane that differs from alpha-amyrin in having the 29-carbon at the 20 position; RN given refers to (3 beta)-isomer. beta-amyrin : A pentacyclic triterpenoid that is oleanane substituted at the 3beta-position by a hydroxy group and containing a double bond between positions 12 and 13. It is one of the most commonly occurring triterpenoids in higher plants.	2.46	2	0	pentacyclic triterpenoid; secondary alcohol	Aspergillus metabolite; plant metabolite
nicosulfuron nicosulfuron: inhibits ACETOLACTATE SYNTHASE; Accent is DuPont brand name. nicosulfuron : A N-sulfonylurea that is 2-(carbamoylsulfamoyl)-N,N-dimethylpyridine-3-carboxamide substituted by a 4,6-dimethoxypyrimidin-2-yl group at the amino nitrogen.	3.03	4	0	N-sulfonylurea; pyridines; pyrimidines	environmental contaminant; herbicide; xenobiotic
sakuranetin sakuranetin: major rice phytoalexin; RN given for ((S)-(-))-isomer; structure in first source. sakuranetin : A flavonoid phytoalexin that is (S)-naringenin in which the hydroxy group at position 7 is replaced by a methoxy group.	3.67	9	0	(2S)-flavan-4-one; 4'-hydroxyflavanones; dihydroxyflavanone; flavonoid phytoalexin; monomethoxyflavanone	antimycobacterial drug; plant metabolite
bilobalide [no description available]	11.11	149	4	sesquiterpene lactone
isoxaben isoxaben : A benzamide obtained by formal condensation of the carboxy group of 2,6-dimethoxybenzoic acid and the amino group of 3-(3-methylpentan-3-yl)-1,2-oxazol-5-amine.	2.01	1	0	benzamides; isoxazoles	cellulose synthesis inhibitor; herbicide
flusilazole flusilazole: structure given in first source. flusilazole : An organosilicon compound that is dimethylsilane in which the hydrogens attached to the silicon are replaced by p-fluorophenyl groups and a hydrogen attached to one of the methyl groups is replaced by a 1H-1,2,4-triazol-1-yl group. It is a broad-sepctrum fungicide used to protect a variety of crops.	2.94	3	0	conazole fungicide; monofluorobenzenes; organosilicon compound; triazole fungicide; triazoles	antifungal agrochemical; EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor; environmental contaminant; xenobiotic
tetracyanoquinodimethane tetracyanoquinodimethane: structure. tetracyanoquinodimethane : A quinodimethane that is p-quinodimethane in which the methylidene hydrogens are replaced by cyano groups.	3.51	2	0	alicyclic compound; nitrile; quinodimethane
oxazolidin-2-one Oxazolidinones: Derivatives of oxazolidin-2-one. They represent an important class of synthetic antibiotic agents.. oxazolidin-2-one : An oxazolidinone that is 1,3-oxazolidine with an oxo substituent at position 2.. oxazolidinone : An oxazolidine containing one or more oxo groups.	3.43	7	0	carbamate ester; oxazolidinone	metabolite
3,4,7,8-tetramethyl-1,10-phenanthroline [no description available]	2.08	1	0
triphenylmethylphosphonium triphenylmethylphosphonium: RN given refers to parent cpd	2.49	2	0
octadecyl palmitate octadecyl palmitate: found in psoriatic nail, but not in normal nails. stearyl palmitate : A palmitate ester resulting from the formal condensation of the carboxy group of palmitic acid with the hydroxy group of stearyl alcohol.	2.25	1	0	hexadecanoate ester; wax ester	coral metabolite; cosmetic
cyclobutanol cyclobutanol: structure in first source	3.59	2	0
4-methoxymethylpyridoxine 4-methoxymethylpyridoxine: RN given refers to parent cpd	2.4	2	0	pyridines
bendamustine hydrochloride [no description available]	2.11	1	0
ethyl protocatechuate ethyl protocatechuate: structure. ethyl 3,4-dihydroxybenzoate : An ethyl ester resulting from the formal condensation of the carboxy group of 3,4-dihydroxybenzoic acid with ethanol. It is the anti-oxidative component of peanut seed testa.	1.98	1	0	catechols; ethyl ester	antibacterial agent; antioxidant; apoptosis inducer; EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor; plant metabolite
1-benzylimidazole 1-benzylimidazole: inhibits human thromboxane synthetase	2.05	1	0
rosiglitazone [no description available]	2.94	4	0	aminopyridine; thiazolidinediones	EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor; ferroptosis inhibitor; insulin-sensitizing drug
isopiperitenone isopiperitenone: structure given in first source	1.99	1	0	p-menthadien-3-one
3,7-dimethyl-7-octen-1-ol Geranium: A plant genus of the family GERANIACEAE. Geranium is also used as a common name for PELARGONIUM.	2.15	1	0
4-methyl-2,4-bis(4-hydroxyphenyl)pent-1-ene 4-methyl-2,4-bis(4-hydroxyphenyl)pent-1-ene: bisphenol A metabolite; structure in first source	2.31	1	0	phenols
d-aspartic acid [no description available]	2.05	1	0	aspartic acid; D-alpha-amino acid	mouse metabolite
asperuloside asperuloside : A iridoid monoterpenoid glycoside isolated from Galium verum.	2.05	1	0	acetate ester; beta-D-glucoside; gamma-lactone; iridoid monoterpenoid; monosaccharide derivative	metabolite
tebuconazole Lynx: A genus in the family FELIDAE comprising felines with long legs, ear tufts, and a short tail.. 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol : A tertiary alcohol that is pentan-3-ol substituted by a 4-chlorophenyl, methyl, methyl, and a 1H-1,2,4-triazol-1-ylmethyl at positions 1, 4, 4 and 3 respectively.. tebuconazole : A racemate composed of equimolar amounts of (R)- and (S)-tebuconazole. A fungicide effective against various smut and bunt diseases in cereals and other field crops.	2.15	1	0	monochlorobenzenes; tertiary alcohol; triazoles
metconazole metconazole : A member of the class of cyclopentanols carrying 1,2,4-triazol-1-ylmethyl and 4-chlorobenzyl and geminal dimethyl substituents at positions 1, 2 and 5 respectively. Used to control a range of fungal infections including alternaria, rusts, fusarium and septoria diseases.	2.31	1	0	conazole fungicide; cyclopentanols; monochlorobenzenes; tertiary alcohol; triazole fungicide; triazoles	antifungal agrochemical; EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor
s-methyl benzo(1,2,3)thiadiazole-7-carbothioate S-methyl benzo(1,2,3)thiadiazole-7-carbothioate: induces system acquired resistance in wheat; structure in first source. acibenzolar-S-methyl : A benzothiadiazole that is the S-methyl thioester derivative of acibenzolar. A profungicide (by hydrolysis of the thioester group to give the corresponding carboxylic acid), it is used as a fungicide and plant activator on a variety of crops, including cotton, chili peppers, lettuce, onions, spinach, tobacco, and tomatoes.	3.56	8	0	benzothiadiazole; thioester	antifungal agrochemical; plant activator; profungicide
alpha-bergamotene alpha-bergamotene: RR (13434-59-4) refers to the (trans)-isomer. alpha-bergamotene : A sesquiterpene consisting of a bicyclo[3.1.1]hept-2-ene skeleton substituted at positions 2 and 6 by methyl groups and at position 6 by a 4-methylpent-3-en-1-yl group.	3.11	5	0	bridged compound; polycyclic olefin; sesquiterpene	plant metabolite; volatile oil component
coenzyme a [no description available]	2.4	2	0	adenosine 3',5'-bisphosphate	coenzyme; Escherichia coli metabolite; mouse metabolite
loganin [no description available]	2.47	2	0	beta-D-glucoside; cyclopentapyran; enoate ester; iridoid monoterpenoid; methyl ester; monosaccharide derivative; secondary alcohol	anti-inflammatory agent; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; EC 3.4.23.46 (memapsin 2) inhibitor; neuroprotective agent; plant metabolite
gentiopicroside gentiopicroside: a secoiridoid in Gentiana with rearrangement to two pyran rings	2.13	1	0	glycoside
nicotine (S)-nicotine : A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has S-configuration. The naturally occurring and most active enantiomer of nicotine, isolated from Nicotiana tabacum.	8.98	72	1	3-(1-methylpyrrolidin-2-yl)pyridine	anxiolytic drug; biomarker; immunomodulator; mitogen; neurotoxin; nicotinic acetylcholine receptor agonist; peripheral nervous system drug; phytogenic insecticide; plant metabolite; psychotropic drug; teratogenic agent; xenobiotic
hecogenin hecogenin: steroidal sapogenin which has been isolated from plants particularly from numerous Agave species; used in prep of steroidal hormones; structure; RN given refers to (3beta,5alpha,25R)-isomer	2.07	1	0	triterpenoid
beta-thujone [no description available]	2.21	1	0	beta-thujone
aucubin [no description available]	2.05	1	0	organic molecular entity	metabolite
2-tyrosine 2-tyrosine: RN given refers to cpd with unspecified isomeric designation. o-tyrosine : A racemate comprising equimolar amounts of D- and L-o-tyrosine.. 2-hydroxyphenylalanine : A phenylalanine derivative that is phenylalanine carrying a hydroxy substituent at position 2 on the benzene ring.	2.1	1	0	non-proteinogenic alpha-amino acid; phenols; phenylalanine derivative
galaxolide galaxolide: musk fragrance; structure given in first source. galaxolide : An organic heterotricyclic compound that is 1,3,4,6,7,8-hexahydrocyclopenta[g]isochromene substituted by methyl groups at positions 4, 6, 6, 7, 8 and 8 respectively. It is a synthetic musk used as a fragrance in cosmetics.	2.13	1	0	isochromenes; organic heterotricyclic compound	fragrance
cadmium telluride cadmium telluride: used in radiation monitoring device	2.08	1	0
4-nitrophenyl beta-d-xyloside 4-nitrophenyl beta-D-xyloside : A xyloside that is beta-D-xylopyranose in which the anomeric hydroxy hydrogen is replaced by a 4-nitrophenyl group.	1.98	1	0	C-nitro compound; xyloside	chromogenic compound
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.	3.97	4	0	amino acid zwitterion; homocysteine; serine family amino acid	fundamental metabolite; mouse metabolite
oryzemate oryzemate: induces disease resistance against rice blast fungus in rice; structure in first source. probenazole : A member of the class of 1,2-benzothiazoles that is 1,2-benzothiazole 1,1-dioxide substituted at position 3 by an allyloxy group. A fungicide used to control rice blast.	2.93	4	0	1,2-benzisothiazole; aromatic ether; benzothiazole fungicide; sulfone	antifungal agrochemical; plant activator
hydroxyisohexyl 3-cyclohexene carboxaldehyde hydroxyisohexyl 3-cyclohexene carboxaldehyde: structure in first source	2.41	2	0
dichlorobis(cyclopentylamine)platinum dichlorobis(cyclopentylamine)platinum: RN given refers to unlabeled cpd(SP-4-2)-isomer; structure	2.65	3	0
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.	2.15	1	0	3',5'-cyclic purine nucleotide; adenyl ribonucleotide; aryl sulfide; organochlorine compound	protein kinase agonist
coronatine coronatine: consists of a coronafacic acid joined by an amide bond to coronamic acid by coronafacate ligase; phytotoxin produced by Pseudomonas syringae; RN given refers to (3aS-(3aalpha,4(1R,2R),6beta,7alpha))-isomer;	7.62	73	0	N-acyl-amino acid
flutriafol flutriafol: fungicide; structure in first source. flutriafol : A racemate comprising an equimolar mixture of (R)- and (S)-flutriafol. A systemic fungicide, it is used to control fungal diseases in cereal crops.. 1-(2-fluorophenyl)-1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanol : A tertiary alcohol that is ethanol in which one of the hydrogens at position 1 is replaced by an p-fluorophenyl group, the other hydrogen at position 1 is replaced by a p-fluorophenyl group, and one of the hydrogens at position 2 is replaced by a 1H-1,2,4-triazol-1-yl group.	2.21	1	0	monofluorobenzenes; tertiary alcohol; triazoles
quinclorac quinclorac: an herbicide. quinclorac : A quinolinemonocarboxylic acid that is quinoline-8-carboxylic acid in which the hydrogens at positions 3 and 7 have been replaced by chlorines. It is used (particularly as its dimethylamine salt, known as quinclorac-dimethylammonium) as a (rather persistent) herbicide for the post-emergence control of weeds in rice, grass and turf. It is not approved for use within the European Union.	2.25	1	0	monocarboxylic acid; organochlorine compound; quinolinemonocarboxylic acid	agrochemical; herbicide; synthetic auxin
prosulfuron prosulfuron: structure in first source	2.02	1	0	triazines
ac 263,222 imazapic: imidazolinone herbicide. imazapic : A racemate comprising equimolar amounts of (R)- and (S)-imazapic. It is a selective imidazolinone herbicide for pre- and post-emergent control of some annual and perennial grasses and broadleaf weeds. It kills plants by inhibiting the activity of the enzyme acetohydroxy acid synthase (AHAS).. 5-methyl-2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]pyridine-3-carboxylic acid : A pyridinemonocarboxylic acid that is 5-methylpyridine-3-carboxylic acid which is substituted at position 2 by a 4,5-dihydro-imidazol-2-yl group, which in turn is substituted at positions 4, 4, and 5 by isopropyl, methyl, and oxo groups, respectively.	2.13	1	0	imidazolines; imidazolone; methylpyridines; pyridinemonocarboxylic acid
primisulfuron primisulfuron: structure in first source	2.02	1	0	benzoic acids
sarsasapogenin [no description available]	2.07	1	0	sapogenin
taraxerol taraxerol: structure. taraxerol : A pentacyclic triterpenoid that is oleanan-3-ol lacking the methyl group at position 14, with an alpha-methyl substituent at position 13 and a double bond between positions 14 and 15.	2.63	2	0	pentacyclic triterpenoid; secondary alcohol	metabolite
cycloartenol [no description available]	2.01	1	0	3beta-sterol; pentacyclic triterpenoid; phytosterols	plant metabolite
n(6)-(delta(2)-isopentenyl)adenine N(6)-dimethylallyladenine : A 6-isopentenylaminopurine in which has the isopentenyl double bond is located between the 2 and 3 positions of the isopentenyl group.	2.78	3	0	6-isopentenylaminopurine	cytokinin
methylumbelliferyl-beta-d-xyloside [no description available]	1.98	1	0
cyclopentane-1,2,3-triol [no description available]	3.07	5	0
gamma-tocopherol gamma-Tocopherol: A natural tocopherol with less antioxidant activity than ALPHA-TOCOPHEROL. It exhibits antioxidant activity by virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus. As in BETA-TOCOPHEROL, it also has three methyl groups on the 6-chromanol nucleus but at different sites.. gamma-tocopherol : A tocopherol in which the chroman-6-ol core is substituted by methyl groups at positions 7 and 8. It is found particularly in maize (corn) oil and soya bean (soybean) oils.	2.47	2	0	tocopherol; vitamin E	algal metabolite; food antioxidant; plant metabolite
nepetalactone nepetalactone: RN given for (4aS-(4aalpha,7alpha,7aalpha))-isomer; structure in first source. trans-cis-nepetalactone : A cyclopentapyran that is (4aS,7aS)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran substituted at position 1 by an oxo group and at positions 4 and 7 by methyl groups, respectively (the 4aS,7S,7aS-diastereomer). An iridoid monoterpenoid isolated from several Nepeta plant species. It exhibits potent repellant activity against house dust mites and mosquitoes.	4.84	32	0
1,2-pentanediol [no description available]	2.02	1	0
glycidyl nitrate glycidyl nitrate: a nitric oxide donor; structure in first source. peptidoglycan : A peptidoglycosaminoglycan formed by alternating residues of beta-(1->4)-linked N-acetylglucosamine and N-acetylmuramic acid {2-amino-3-O-[(S)-1-carboxyethyl]-2-deoxy-D-glucose} residues. Attached to the carboxy group of the muramic acid is a peptide chain of three to five amino acids.	2.05	1	0
isohumulone isohumulone: hop-derived compound	6.69	20	3	monoterpenoid
dithiobis(succinimidylpropionate) dithiobis(succinimidylpropionate): used to study interactions of structural proteins; RN given refers to unlabeled cpd	1.99	1	0
arabitol arabitol: RN given refers to cpd without isomeric designation. arabinitol : A pentitol that is the sugar alcohol produced by the reduction of arabinose or lyxose. It is found in serum or urine of human infected with Candida albicans.. D-arabinitol : The D-enantiomer of arabinitol.	2.03	1	0	arabinitol
pyrimidine dimers Pyrimidine Dimers: Dimers found in DNA chains damaged by ULTRAVIOLET RAYS. They consist of two adjacent PYRIMIDINE NUCLEOTIDES, usually THYMINE nucleotides, in which the pyrimidine residues are covalently joined by a cyclobutane ring. These dimers block DNA REPLICATION.	1.99	1	0
pyrroline pyrroline: RN given refers to cpd with unspecified locant for dihydro moiety. pyrroline : Any organic heteromonocyclic compound with a structure based on a dihydropyrrole.	2.73	3	0	pyrroline
dansyl hydrazine [no description available]	1.96	1	0
glucuronic acid Glucuronic Acid: A sugar acid formed by the oxidation of the C-6 carbon of GLUCOSE. In addition to being a key intermediate metabolite of the uronic acid pathway, glucuronic acid also plays a role in the detoxification of certain drugs and toxins by conjugating with them to form GLUCURONIDES.. D-glucuronic acid : The D-enantiomer of glucuronic acid.. D-glucopyranuronic acid : A D-glucuronic acid in cyclic pyranose form.	2.4	2	0	D-glucuronic acid	algal metabolite
2,6-dichloroisonicotinic acid 2,6-dichloroisonicotinic acid: an ascorbate peroxidase antagonist; RN given refers to parent cpd. 2,6-dichloroisonicotinic acid : A member of the class of pyridines that is isonicotinic acid which is substituted by chlorine at positions 2 and 6.	3.26	6	0	monocarboxylic acid; organochlorine compound; pyridines	EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor
1-phenazinecarboxylic acid 1-phenazinecarboxylic acid: from Streptomyces cinnamonensis; RN given refers to parent cpd; structure given in first source. phenazine-1-carboxylic acid : An aromatic carboxylic acid that is phenazine substituted at C-1 with a carboxy group.	2.1	1	0	aromatic carboxylic acid; monocarboxylic acid; phenazines	antifungal agent; antimicrobial agent; bacterial metabolite
allenolic acid allenolic acid: structure in first source	2.05	1	0	naphthols
carbobenzoxyglycylphenylalanine amide carbobenzoxyglycylphenylalanine amide: used as substrate for metalloendopeptidases; RN given refers to (L)-isomer	1.98	1	0
2,5-dihydroxypyridine pyridine-2,5-diol : A dihydroxypyridine that is pyridine substituted by hydroxy groups at positions 2 and 5.	4.9	1	1	dihydroxypyridine	mouse metabolite
diosgenin [no description available]	3.05	4	0	3beta-sterol; hexacyclic triterpenoid; sapogenin; spiroketal	antineoplastic agent; antiviral agent; apoptosis inducer; metabolite
isosteviol isosteviol: an antihyperglycemic agent; obtained by acid hydrolysis of stevioside; was indexed to steviol 1985-2007	2.06	1	0	diterpenoid
phorbolol myristate acetate [no description available]	1.97	1	0
combretastatin combretastatin: cytotoxic principle from South African tree COMBRETUM caffrum; structure given in first source; acts at COLCHICINE site of TUBULIN	2.01	1	0
virantmycin virantmycin: has potent antifungal activity & potent inhibitory activity against DNA & RNA viruses; from Streptomyces nitrosporeus No. AM-2722; structure in 2nd source	2.21	1	0
loliolide loliolide: RN given refers to (6S-cis)-isomer	2.6	1	0	benzofurans	metabolite
ethyl magnesium bromide ethyl magnesium bromide: prepard from magnesium turnings & ethyl bromide	2.02	1	0
2-amino-4-phenylbutyric acid 2-amino-4-phenylbutanoic acid: structure in first source	2.08	1	0
2,3-bis(4-hydroxyphenyl)-propionitrile 2,3-bis(4-hydroxyphenyl)-propionitrile: a selective estrogen receptor beta agonist or modulator. also called DPN compound. 2,3-bis(4-hydroxyphenyl)propionitrile : A nitrile that is acetonitrile in which one of the hydrogens is replaced by a 4-hydroxyphenyl group while a second hydrogen is replaced by a 4-hydroxybenzyl group. It is a specific agonist for estrogen receptor beta (ERbeta).	2.8	3	0	nitrile; phenols	estrogen receptor agonist
4,8-dimethyl-1,3,7-nonatriene 4,8-dimethyl-1,3,7-nonatriene: structure in first source	3.34	6	0
ethyl-3-(n-n-butyl-n-acetyl)aminopropionate ethyl-3-(N-n-butyl-N-acetyl)aminopropionate: an insect repellent; structure in first source	2.1	1	0	acetamides; ethyl ester; tertiary carboxamide
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.	5.67	24	0	cobalt group element atom; metal allergen	micronutrient
p-methoxy-n-methylphenethylamine p-Methoxy-N-methylphenethylamine: A potent mast cell degranulator. It is involved in histamine release.. N,O-dimethyltyramine : A secondary amino compound that is tyramine in which the hydrogen of the phenolic hydroxy group has been replaced by a methyl group.	2.05	1	0	aromatic ether; secondary amino compound	metabolite
fulvestrant Fulvestrant: An estradiol derivative and estrogen receptor antagonist that is used for the treatment of estrogen receptor-positive, locally advanced or metastatic breast cancer.. fulvestrant : A 3-hydroxy steroid that is 17beta-estradiol in which the 7alpha hydrogen has been replaced by a nonyl group in which one of the hydrogens of the terminal methyl has been replaced by a (4,4,5,5,5-pentafluoropentyl)sulfinyl group. An estrogen receptor antagonist, it is used in the treatment of breast cancer.	3.68	9	0	17beta-hydroxy steroid; 3-hydroxy steroid; organofluorine compound; sulfoxide	antineoplastic agent; estrogen antagonist; estrogen receptor antagonist
1,2-bis(2-aminophenoxy)ethane-n,n,n',n'-tetraacetic acid 1,2-bis(2-aminophenoxy)ethane-N,N,N',N'-tetraacetic acid: structure in first source	2	1	0	polyamino carboxylic acid; tetracarboxylic acid	chelator
chlorates Chlorates: Inorganic salts of chloric acid that contain the ClO3- ion.	2.37	2	0	chlorine oxoanion; monovalent inorganic anion
tert-butylbicyclophosphorothionate tert-butylbicyclophosphorothionate: binds to GABA & ion recognition sites; structure given in first source	2.4	2	0	organic thiophosphate
u 73122 1-(6-((3-methoxyestra-1,3,5(10)-trien-17-yl)amino)hexyl)-1H-pyrrole-2,5-dione: structure given in first source. U-73122 : An aza-steroid that is 3-O-methyl-17beta-estradiol in which the 17beta-hydroxy group is replaced by a 6-(maleimid-1-yl)hexylamino group. An inibitor of phospholipase C.	2.4	2	0	aromatic ether; aza-steroid; maleimides	EC 3.1.4.11 (phosphoinositide phospholipase C) inhibitor
arginyl-glycyl-aspartic acid arginyl-glycyl-aspartic acid: amino acid sequence of basic unit of widespread cellular recognition system	2.02	1	0	oligopeptide
1,4-dihydropyridine [no description available]	2.06	1	0
4-(methylnitrosamino)-1-(3-pyridyl)-1-butan-1-ol 4-(methylnitrosamino)-1-(3-pyridyl)-1-butan-1-ol: structure in first source. 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol : A member of the class of nitrosamines that is butan-1-ol substituted by a pyridin-3-yl group at position 1 and by a methyl(nitroso)amino group at position 4. It is a major metabolite of nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), which is a carcinogen found in tobacco and responsible for inducing lung cancer in smokers.	2.07	1	0	nitrosamine; pyridines; secondary alcohol	biomarker; carcinogenic agent; human urinary metabolite
s-nitrosoglutathione [no description available]	2.44	2	0	glutathione derivative; nitrosothio compound	bronchodilator agent; nitric oxide donor; platelet aggregation inhibitor; signalling molecule
diacetyldichlorofluorescein diacetyldichlorofluorescein: stable storage form of dichlorofluorescein	2.13	1	0
benz(j)aceanthrylene [no description available]	1.99	1	0	phenanthrenes
cyanates Cyanates: Organic salts of cyanic acid containing the -OCN radical.. cyanates : Salts and esters of cyanic acid, HOC#N; compounds carrying the cyanate functional group -O-C#N.. isocyanates : Organonitrogen compounds that are derivatives of isocyanic acid; compounds containing the isocyanate functional group -N=C=O (as opposed to the cyanate group, -O-C#N).	3.08	5	0
bradykinin, des-arg(9)- bradykinin, des-Arg(9)-: RN given refers to parent cpd	1.98	1	0	oligopeptide	bradykinin receptor B2 agonist
benz(l)aceanthrylene benz(l)aceanthrylene: structure given in first source	1.99	1	0	phenanthrenes
cgp 35348 CGP 35348: antagonizes both GABA-A and GABA-B receptors	2.13	1	0
15,16-dihydrocyclopenta(a)phenanthren-17-one 15,16-dihydrocyclopenta(a)phenanthren-17-one: structure	1.95	1	0
methoctramine methoctramine: structure given in first source. methoctramine : A tetramine that is N,N'-bis(6-aminohexyl)octane-1,8-diamine where the primary amino groups both carry 2-methoxybenzyl substituents.. methoctramine tetrahydrochloride : A hydrochloride obtained by combining methoctramine with four molar equivalents of hydrochloric acid.	2.02	1	0	hydrochloride	muscarinic antagonist
aceanthrylene aceanthrylene: structure given in first source	2.03	1	0	ortho- and peri-fused polycyclic arene
saikosaponin d [no description available]	2.45	2	0
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	3.06	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
hypotaurine [no description available]	2.05	1	0	aminosulfinic acid; zwitterion	human metabolite; metabolite; mouse metabolite
tabtoxin tabtoxin: dipeptide containing tabtoxinine-beta-lactam with threonine; structure. tabtoxin : A monobactam phytotoxic dipeptide produced by Pseudomonas syringae, that causes wildfire disease in tobacco.	3.16	1	0	dipeptide; L-threonine derivative; monobactam; secondary alcohol	bacterial metabolite; toxin
geniposide [no description available]	2	1	0	terpene glycoside
procyanidin Proanthocyanidins: Dimers and oligomers of flavan-3-ol units (CATECHIN analogs) linked mainly through C4 to C8 bonds to leucoanthocyanidins. They are structurally similar to ANTHOCYANINS but are the result of a different fork in biosynthetic pathways.	3.73	9	0	proanthocyanidin
phosphites Phosphites: Inorganic salts or organic esters of phosphorous acid that contain the (3-)PO3 radical. (From Grant & Hackh's Chemical Dictionary, 5th ed). phosphite(3-) : A trivalent inorganic anion obtained by removal of all three protons from phosphorous acid.	2.99	4	0	phosphite ion; trivalent inorganic anion
(2-(trimethylammonium)ethyl)methanethiosulfonate (2-(trimethylammonium)ethyl)methanethiosulfonate: RN given for bromide; used in dopamine analysis	2.02	1	0
1,9-dideoxyforskolin [no description available]	2.69	3	0	acetate ester; labdane diterpenoid; organic heterotricyclic compound	plant metabolite
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).	2.63	2	0	hydrochloride	immunosuppressive agent; prodrug; sphingosine-1-phosphate receptor agonist
daidzin daidzin: a potent, selective, and reversible inhibitor of human mitochondrial aldehyde dehydrogenase. daidzein 7-O-beta-D-glucoside : A glycosyloxyisoflavone that is daidzein attached to a beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage. It is used in the treatment of alcohol dependency (antidipsotropic).	3	4	0	7-hydroxyisoflavones 7-O-beta-D-glucoside; hydroxyisoflavone; monosaccharide derivative	plant metabolite
n(g)-iminoethylornithine [no description available]	2.08	1	0	L-alpha-amino acid
triptolide [no description available]	3.05	4	0	diterpenoid; epoxide; gamma-lactam; organic heteroheptacyclic compound	antispermatogenic agent; plant metabolite
3,5-dihydroxyphenylglycine 3,5-dihydroxyphenylglycine: a potent agonst of metabotropic glutamate receptors	2	1	0	alpha-amino acid
asiaticoside [no description available]	3.14	5	0
proanthocyanidin proanthocyanidin: RN given refers to proanthocyanidin A; Cannabinoid Receptor CB1 antagonist. proanthocyanidin : A flavonoid oligomer obtained by the the condensation of two or more units of hydroxyflavans.	2.11	1	0
parthenolide [no description available]	2.11	1	0	germacranolide
schizandrin b schizandrin B: a phytogenic antineoplastic agent with anti-inflammatory activity; isolated from Schisandra plant	2.1	1	0
1-hexadecyl-2-acetyl-glycero-3-phosphocholine Platelet Activating Factor: A phospholipid derivative formed by PLATELETS; BASOPHILS; NEUTROPHILS; MONOCYTES; and MACROPHAGES. It is a potent platelet aggregating agent and inducer of systemic anaphylactic symptoms, including HYPOTENSION; THROMBOCYTOPENIA; NEUTROPENIA; and BRONCHOCONSTRICTION.. 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine : A 2-acetyl-1-alkyl-sn-glycero-3-phosphocholine betaine which has hexadecyl as the alkyl group. PAF is a potent phospholipid activator and mediator of many leukocyte functions, including platelet aggregation, inflammation, and anaphylaxis.	3.79	3	0	2-acetyl-1-alkyl-sn-glycero-3-phosphocholine	antihypertensive agent; beta-adrenergic antagonist; bronchoconstrictor agent; hematologic agent; vasodilator agent
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.	4.09	15	0
hydnocarpic acid hydnocarpic acid: cyclopentenyl fatty acid; component of chaulmoogra oil. hydnocarpic acid : A cyclopentenyl fatty acid consisting of undecanoic acid having a cyclopent-2-enyl group at the 11-position.	2.36	2	0	cyclopentenyl fatty acid; long-chain fatty acid; monounsaturated fatty acid
1-phenyl-2-decanoylamino-3-morpholino-1-propanol RV 538: noninactivating inhibitor of ceramide-UDPG glucosyltransferase; RN given for unspecified HCl; structure given in first source	1.99	1	0
metaphit metaphit: site-directed acylating agent of phencyclidine receptors in rat brain; structure given in first source	2.03	1	0
valerates Valerates: Derivatives of valeric acid, including its salts and esters.	2.87	4	0	short-chain fatty acid anion; straight-chain saturated fatty acid anion	plant metabolite
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.	3.05	1	0
monochlorobimane monochlorobimane: marker for glutathione	2.01	1	0	organochlorine compound; pyrazolopyrazole	fluorochrome
tanshinone tanshinone: from root of Salvia miltiorrhiza Bunge; RN given refers to tanshinone I; cardioprotective agent and neuroprotective agent	4.61	23	0	abietane diterpenoid	anticoronaviral agent
coronafacic acid coronafacic acid: a polyketide that is coupled to coronamic acid by coronafacate ligase to form coronatine; structure given in first source; RN refers to (3aS-(3aalpha,6beta,7aalpha))-isomer	2.99	4	0	ketone
soyasapogenol b soyasapogenol B: RN given for (3beta,4beta,22beta)-isomer; structure in first source. soyasapogenol B : A pentacyclic triterpenoid that is oleanane containing a double bond between positions 12 and 13 and substituted by hydroxy groups at the 3beta, 22beta and 24-positions.	2.01	1	0	pentacyclic triterpenoid
2-(2,3-dicarboxycyclopropyl)glycine [no description available]	2.45	2	0
brassinolide brassinolide: plant growth promoting steroidal lactone from rape pollen; RN given refers to (2alpha,3alpha,5alpha,22R,23R,24S)-isomer; structure in first source	5.91	18	0	22-hydroxy steroid; 23-hydroxy steroid; 2alpha-hydroxy steroid; 3alpha-hydroxy steroid; brassinosteroid	plant growth stimulator; plant hormone
ginkgolide a [no description available]	5.51	15	1	diterpene lactone
glycolithocholic acid glycolithocholic acid: RN given refers to (3alpha,5beta)-isomer. glycolithocholic acid : The glycine conjugate of lithocholic acid.	1.98	1	0	bile acid glycine conjugate; N-acylglycine
taraxasterol taraxasterol: from Cirsium segetum. taraxasterol : A pentacyclic triterpenoid that is taraxastane with a beta-hydroxy group at position 3.	2.84	3	0	pentacyclic triterpenoid; secondary alcohol	anti-inflammatory agent; metabolite
asiatic acid [no description available]	2.08	1	0	monocarboxylic acid; pentacyclic triterpenoid; triol	angiogenesis modulating agent; metabolite
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.	2.95	4	0	fatty acid anion 8:0; straight-chain saturated fatty acid anion	human metabolite; Saccharomyces cerevisiae metabolite
tris(2-carboxyethyl)phosphine tris(2-carboxyethyl)phosphine: water-soluble reagent which irreversibly reduces disulfides to thiols at room temperature & is active below neutral pH; used for quantitation of iodine and iodate. TCEP : A tertiary phosphine in which phosphane is substituted with three 2-carboxyethyl groups. It is a commonly used reducing agent.	4.9	1	1	phosphine derivative; tricarboxylic acid	reducing agent
ah 6809 6-isopropoxy-9-oxoxanthene-2-carboxylic acid: structure given in UD	2.05	1	0	xanthones
soyasaponin bb soyasaponin Bb: has activity against polycystic kidney disease; isolated from soybean; structure in first source. soyasaponin I : A triterpenoid saponin that is composed of soyasapogenol B having an alpha-L-rhamnopyranosyl-(1->2)-beta-D-galactopyranosyl-(1->2)-beta-D-glucopyranosiduronic acid moiety attached at the 3-position via a glycosidic linkage.	2.01	1	0	carbohydrate acid derivative; pentacyclic triterpenoid; trisaccharide derivative; triterpenoid saponin	sialyltransferase inhibitor
benzyl-alpha-n-acetylgalactosamine benzyl-alpha-N-acetylgalactosamine: an inhibitor of mucin glycosylation	2.39	2	0
florox reagent Florox Reagent: reagent for analysis of ketosteroids; structure	2.46	2	0
celastrol [no description available]	2.57	2	0	monocarboxylic acid; pentacyclic triterpenoid	anti-inflammatory drug; antineoplastic agent; antioxidant; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; Hsp90 inhibitor; metabolite
imidodiphosphonic acid imidodiphosphonic acid: in combination with technetrium, a superior radiopharmaceutical for myocardial infarct imaging; RN given refers to parent cpd	2.25	1	0
dammarenediol dammarenediol: RN refers to (3beta)-isomer; structure given in first source	2.79	3	0
phenoxy radical phenoxy radical : An organic radical generated from phenol.	2.01	1	0	organic radical
carbene carbene: electrically neutral species H2C: and its derivatives, in which the carbon is covalently bonded to two univalent groups of any kind or a divalent group and bears two nonbonding electrons; carbene is the name of the parent hydride :CH2 ; hence, the name dichlorocarbene for :CCl2. However, names for acyclic and cyclic hydrocarbons containing one or more divalent carbon atoms are derived from the name of the corresponding all-4-hydrocarbon using the suffix -ylidene; methylene carbene also available. carbene : The electrically neutral species H2C(2.) and its derivatives, in which the carbon is covalently bonded to two univalent groups of any kind or a divalent group and bears two nonbonding electrons, which may be spin-paired (singlet state) or spin-non-paired (triplet state).	4.82	31	0	carbene; methanediyl
cyclopropene cyclopropene: structure. cyclopropene : A cycloalkene that consists of cyclopropane having a double bond in the ring. The parent of the class of cyclopropenes.	2.44	2	0	cycloalkene; cyclopropenes
diazene [no description available]	2.44	2	0	nitrogen hydride
disiloxane [no description available]	2.06	1	0	siloxane
peroxynitrous acid Peroxynitrous Acid: A potent oxidant synthesized by the cell during its normal metabolism. Peroxynitrite is formed from the reaction of two free radicals, NITRIC OXIDE and the superoxide anion (SUPEROXIDES).	2.01	1	0	nitrogen oxoacid
fullerene c60 Fullerenes: A polyhedral CARBON structure composed of around 60-80 carbon atoms in pentagon and hexagon configuration. They are named after Buckminster Fuller because of structural resemblance to geodesic domes. Fullerenes can be made in high temperature such as arc discharge in an inert atmosphere.. fullerene : A compound composed solely of an even number of carbon atoms, which form a cage-like fused-ring polycyclic system with twelve five-membered rings and the rest six-membered rings. The term has been broadened to include any closed cage structure consisting entirely of three-coordinate carbon atoms.	2.97	4	0	fullerene	geroprotector
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.	2.59	2	0	methanesulfonate salt	anticoronaviral agent; antineoplastic agent; apoptosis inducer; tyrosine kinase inhibitor
tazobactam Tazobactam: A penicillanic acid and sulfone derivative and potent BETA-LACTAMASE inhibitor that enhances the activity of other anti-bacterial agents against beta-lactamase producing bacteria.. tazobactam : A member of the class of penicillanic acids that is sulbactam in which one of the exocyclic methyl hydrogens is replaced by a 1,2,3-triazol-1-yl group; used (in the form of its sodium salt) in combination with ceftolozane sulfate for treatment of complicated intra-abdominal infections and complicated urinary tract infections.	3.21	1	0	penicillanic acids; triazoles	antiinfective agent; antimicrobial agent; EC 3.5.2.6 (beta-lactamase) inhibitor
cephamycin c cephamycin C: produced from O-carbamoyldeacetylcephalosporin in C by cell-free extracts of Streptomyces clavuligerus; RN given refers to cpd without isomeric designation; structure given in first source. cephamycin C : One of three naturally occurring cephamycin antibiotics, differing from the A and B forms in its carbamoyloxymethyl substituent at C-3.	1.96	1	0
nnc 711 NNC 711: structure in first source	2.42	2	0
angiotensin ii, des-phe(8)- Ile(5)-angiotensin II (1-7) : An angiotensin compound consisting of the linear heptapeptide sequence L-Asp-L-Arg-L-Val-L-Tyr-L-Ile-L-His-L-Pro.	2.31	1	0	amino acid zwitterion; angiotensin	vasodilator agent
cyclic adp-ribose Cyclic ADP-Ribose: A pyridine nucleotide that mobilizes CALCIUM. It is synthesized from nicotinamide adenine dinucleotide (NAD) by ADP RIBOSE CYCLASE.	2.49	2	0	cyclic purine nucleotide; nucleotide-sugar	metabolite; ryanodine receptor agonist
ramatroban [no description available]	2.08	1	0	organic molecular entity
1-((3,5-dichloro)-2,6-dihydroxy-4-methoxyphenyl)-1-hexanone 1-((3,5-dichloro)-2,6-dihydroxy-4-methoxyphenyl)-1-hexanone: structure given in first source. 1-(3,5-dichloro-2,6-dihydroxy-4-methoxyphenyl)hexan-1-one : A differentiation-inducing factor that is hexaphenone bearing two chloro substituents at positions 3 and 5, two hydroxy substituents at positions 2 and 6 as well as a single methoxy substituent at position 4. A secreted, chlorinated molecule that controls cell fate during development of Dictyostelium cells.	2.44	2	0	dichlorobenzene; differentiation-inducing factor; monomethoxybenzene; resorcinols	eukaryotic metabolite; signalling molecule
rmi 12330a RMI 12330A: adenyl cyclase inhibitor in rat liver; RN given refers to (cis)-isomer; NM refers to HCl, (cis)-isomer; structure	2.64	3	0
n(omega)-hydroxyarginine N(omega)-hydroxyarginine: can cause vasorelaxation of bovine intrapulmonary artery; structure given in first source. N(5)-[(Z)-amino(hydroxyimino)methyl]-L-ornithine : An N(5)-[amino(hydroxyimino)methyl]-L-ornithine in which the double bond has Z-configuration.	2.02	1	0	amino acid zwitterion; N(5)-[(E)-amino(hydroxyimino)methyl]ornithine; N(5)-[(hydroxyamino)(imino)methyl]ornithine; N(5)-[(Z)-amino(hydroxyimino)methyl]ornithine; N(5)-[amino(hydroxyimino)methyl]-L-ornithine; N(5)-[amino(hydroxyimino)methyl]ornithine; N(omega)-hydroxy-L-arginine
lysyl-aspartyl-glutamyl-leucine lysyl-aspartyl-glutamyl-leucine: retains type II surface membrane proteins in the endoplasmic reticulum; RN refers to all (L)-isomer	1.99	1	0
gamma-glutamylcysteine L-gamma-glutamyl-L-cysteine : A molecular entity formed when L-cysteine amino group binds to the gamma-carbonyl of L-glutamic acid.	2.49	2	0	gamma-glutamylcysteine	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
e 64 E 64: cysteine protease inhibitor of microbial origin, which inhibits cathepsin B (EC 3.4.22.1) and cathepsin L (EC 3.4.22.-)	2.02	1	0	dicarboxylic acid monoamide; epoxy monocarboxylic acid; guanidines; L-leucine derivative; zwitterion	antimalarial; antiparasitic agent; protease inhibitor
dehydroalanine 2-ammonioprop-2-enoate : An amino acid zwitterion resulting from a transfer of a proton from the carboxy group to the amino group of 2-aminoacrylic acid.. 2-aminoacrylic acid : A 2,3-dehydroamino acid that is alanine which has been dehydrogenated to introduce a double bond between positions 2 and 3.	2.04	1	0	2,3-dehydroamino acid; alpha,beta-unsaturated monocarboxylic acid; amino acid zwitterion; enamine; non-proteinogenic alpha-amino acid	alkylating agent; human metabolite; mouse metabolite
mannostatin a mannostatin A: structure given in first source; isolated from Streptoverticillium verticilllus. mannostatin A : An amino cyclitol that is cyclopentane substituted by hydroxy groups at positions 1, 2 and 3, by an amino group at positon 4, and by a methylsulfanediyl group at position 5 (the 1R,2R,3R,4S,5R-stereoisomer). It is isolated from the soil bacterium Streptoverticillium verticillium.	10.11	14	0	amino cyclitol; methyl sulfide; triol	bacterial metabolite; EC 3.2.1.114 (mannosyl-oligosaccharide 1,3-1,6-alpha-mannosidase) inhibitor; EC 3.2.1.24 (alpha-mannosidase) inhibitor
rubimaillin rubimaillin: structure given in first source. rubimaillin : A benzochromene that is 2H-benzo[h]chromene which is substituted by two methyl groups at position 2, a methoxycarbonyl group at position 5, and a hydroxy group at position 6. Found in the Chinese medical plant Rubia cordifola, It has an anti-cancer effect by inhibition of TNF-alpha-induced NF-kappaB activation. It is also a dual inhibitor of acyl-CoA:cholesterol acyltransferase 1 and 2 (ACAT1 and ACAT2), but is more selective for the ACAT2 isozyme.	2.08	1	0	benzochromene; methyl ester; phenols	acyl-CoA:cholesterol acyltransferase 2 inhibitor; anti-inflammatory agent; antineoplastic agent; apoptosis inducer; neuroprotective agent; NF-kappaB inhibitor; plant metabolite
picaridin picaridin: picaridin is the (R,S)-isomer; an insect repellent	2.1	1	0	carboxylic acid; piperidines
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	2.13	1	0
hydantocidin hydantocidin: structure given in first source; from Streptomyces hydroscopicus	3.16	1	0
u 78753e U 78753E: RN given not in Chemline 7/26/83; structure given in first source	3.06	5	0
dibromobimane dibromobimane : A pyrazolopyrazole that consists of 1H,7H-pyrazolo[1,2-a]pyrazole-1,7-dione bearing two methyl substituents at positions 2 and 6 as well as two bromomethyl substituents at positions 3 and 5.	2.06	1	0	organobromine compound; pyrazolopyrazole	fluorochrome
factor xiiib factor XIIIb: deficiency of this cpd causes Type I factor XIII deficiency	1.99	1	0
pre 084 2-(4-morpholino)ethyl-1-phenylcyclohexane-1-carboxylate: structure given in first source	2.97	4	0	morpholines
5'-noraristeromycin 5'-noraristeromycin: structure given in first source	2.03	1	0
methotrexate [no description available]	2.63	3	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
pseudomonas aeruginosa autoinducer Pseudomonas aeruginosa autoinducer: autoinducer required for expression of Pseudomonas aeruginosa virulence genes; structure given in first source. N-(3-oxododecanoyl)homoserine lactone : A N-acyl homoserine lactone that is the monocarboxylic acid amide arising from formal condensation of homoserine lactone with 3-oxododecanoic acid.	2.03	1	0	N-acyl homoserine lactone
ly 293558 tezampanel: structure given in first source; an AMPA receptor antagonist	2.89	3	0
dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylate dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylate: stable deriv of nifedipine; structure given in first source	2.04	1	0	phenylpyridine
cyanidin cyanidin: RN given refers to parent cpd; structure. cyanidin cation : An anthocyanidin cation that is flavylium substituted at positions 3, 3', 4', 5 and 7 by hydroxy groups.	2.52	2	0	5-hydroxyanthocyanidin	antioxidant; metabolite; neuroprotective agent
sdz pco 400 SDZ PCO 400: a potassium channel opening drug	4.07	15	0	1-benzopyran
3-mercapto-3,3-cyclopentamethylenepropionic acid [no description available]	4.21	5	0
kifunensine kifunensine: inhibitor of the glycoprotein processing mannosidase I; from actinomycete Kitasatosporia kifunense 9482; structure given in first source; RN given refers to (5R-(5alpha,6beta,7alpha,8alpha,8aalpha))-isomer; RN for cpd without isomeric designation not avail 10/90	3.07	1	0
histidyl-aspartyl-glutamyl-leucine histidyl-aspartyl-glutamyl-leucine: HDEL intracellular distribution is characteristic of plant endoplasmic reticulum (ER)	1.99	1	0
umifenovir umifenovir: an antiviral agent	3.61	2	0	indolyl carboxylic acid
1-methylspermidine 1-methylspermidine: RN & structure given in first source; RN given refers to parent cpd	3.56	1	1
cgp 52432 [no description available]	2.08	1	0	dichlorobenzene
omega-n-methylarginine omega-N-Methylarginine: A competitive inhibitor of nitric oxide synthetase.. N(omega)-methyl-L-arginine : A L-arginine derivative with a N(omega)-methyl substituent.	2.01	1	0	amino acid zwitterion; arginine derivative; guanidines; L-arginine derivative; non-proteinogenic L-alpha-amino acid
(3-(1-((3-(cyclohexylmethyl)hydroxyphosphinyl)-2-hydroxypropyl)amino)ethyl)benzoic acid (3-(1-((3-(cyclohexylmethyl)hydroxyphosphinyl)-2-hydroxypropyl)amino)ethyl)benzoic acid: RN given for (mono-Li salt,(S-(R,S)))-isomer	2.42	2	0
4-nitro-2-(3-phenylpropylamino)benzoate 4-nitro-2-(3-phenylpropylamino)benzoate: chloride channel antagonist	2.13	1	0
1-amino-2-ethylcyclopropane-1-carboxylic acid 1-amino-2-ethylcyclopropane-1-carboxylic acid: an ethylcyclopropyl amino-acid derived from isoleucine; it may be coupled to coronafacic acid by coronafacate ligase to form coronatine; substrate of malonyltransferase & inhibitor of 1-aminocyclopropane-1-carboxylic acid malonyltransferase; RN given refers to cpd without isomeric designation	2.03	1	0	amino monocarboxylic acid
castasterone castasterone: a brassinosteroid; RN refers to ((2alpha,3alpha,5alpha,22R,23R,24S)-isomer; structure in first source	2.21	1	0	22-hydroxy steroid; 23-hydroxy steroid; 2alpha-hydroxy steroid; 3alpha-hydroxy steroid; 6-oxo steroid; brassinosteroid	plant growth stimulator
carbapenems [no description available]	4.9	1	1
ganglerone ganglerone: RN given refers to parent cpd	1.96	1	0
xylose xylopyranose: structure in first source	3.26	6	0	D-xylose
cd 437 CD 437: selective for retinoic acid receptors gamma. CD437 : A naphthoic acid that is 6-phenylnaphthylene-2-carboxyic acid in which the phenyl substituent has been substituted at positions 3 and 4 by adamant-1-yl and hydroxy groups, respectively. It acts as a selective agonist of retinoic acid receptor (RAR)gamma and induces cell cycle arrest and apoptosis in various cancer cells.	2.6	1	0	adamantanes; monocarboxylic acid; naphthoic acid; phenols	apoptosis inducer; retinoic acid receptor gamma agonist
fulvene fulvene: structure. fulvene : An organic cyclic compound that consists of cyclopentadiene bearing a methylene substituent. The parent of the class of fulvenes.	7.64	58	0	fulvenes
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.	5.3	3	1	beta-lactam antibiotic allergen; beta-lactam
m 8218 M 8218: structure given in first source	4.9	8	0
cyclopropenone cyclopropenone: structure in first source. cyclopropenone : Three-membered alicyclic ketones containing a single C=C double bond.	2.48	2	0
cyclohexadienone cyclohexadienone: structure in first source	2.07	1	0
sperm motility inhibitor 2 [no description available]	2.41	2	0
3-cyclobutene-1,2-dione 3-cyclobutene-1,2-dione: a cyclic diketo compound; structure in first source	2.02	1	0
proline Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.	12.93	36	1	amino acid zwitterion; glutamine family amino acid; L-alpha-amino acid; proline; proteinogenic amino acid	algal metabolite; compatible osmolytes; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
cucurbitaceae Cucurbitaceae: The gourd plant family of the order Violales, subclass Dilleniidae, class Magnoliopsida. It is sometimes placed in its own order, Cucurbitales. 'Melon' generally refers to CUCUMIS; CITRULLUS; or MOMORDICA.	3.13	5	0
3-methyl-2-butene-1-thiol [no description available]	2.03	1	0	alkanethiol
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.	4.16	3	1	secondary alpha-hydroxy ketone; tetracyclic diterpenoid	antimalarial; antineoplastic agent; photosensitizing agent
perifosine [no description available]	2.08	1	0	ammonium betaine; phospholipid	EC 2.7.1.137 (phosphatidylinositol 3-kinase) 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).	2.48	2	0	azetidines; beta-lactam; organofluorine compound	anticholesteremic drug; antilipemic drug; antimetabolite
2-hexadecynoic acid 2-hexadecynoic acid: RN given refers to parent cpd	3.51	1	0	long-chain fatty acid
1-methylcyclopropene 1-methylcyclopropene: do not confuse with 1-methylcyclopropane. 1-methylcyclopropene : A member of the class of cyclopropenes that is cyclopropene in which the hydrogen at position 1 has been replaced by a methyl group. A gas at room temperture and pressure, it is a (synthetic) ethylene perception inhibitor and is used to prolong the life of cut and potted flowers, other ornamental plants, and fruit.	3.78	10	0	cycloalkene; cyclopropenes	agrochemical; plant growth regulator
ribulose ribulose: 5-carbon keto sugar; minor descriptor (75-85); on-line & Index Medicus search PENTOSES (75-85); RN given refers to (erythro)-isomer	2.08	1	0	ribulose	Escherichia coli metabolite; human metabolite
2-aminocyclohexanecarboxylic acid 2-aminocyclohexanecarboxylic acid: RN given for (trans)-isomer; structure in first source	2	1	0
beta-phenylisoserine beta-phenylisoserine: structure in first source	2.03	1	0
salicylic acid glucoside salicylic acid glucoside: structure given in first source; induces pathogenesis-related protein expression in tobacco; involved in systemic acquired resistance. 2-(D-glucosyloxy)benzoic acid : A monosaccharide derivative that is salicylic acid in which the phenolic hydrogen is replaced by a D-glucosyl residue.	2.44	2	0	benzoic acids; D-glucoside; monosaccharide derivative
dirhodium tetraacetate dirhodium tetraacetate: structure given in first source	3.53	2	0
moxifloxacin Moxifloxacin: A fluoroquinolone that acts as an inhibitor of DNA TOPOISOMERASE II and is used as a broad-spectrum antibacterial agent.. moxifloxacin : A quinolone that consists of 4-oxo-1,4-dihydroquinoline-3-carboxylic acid bearing a cyclopropyl substituent at position 1, a fluoro substitiuent at position 6, a (4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl group at position 7 and a methoxy substituent at position 8. A member of the fluoroquinolone class of antibacterial agents.	2.25	1	0	aromatic ether; cyclopropanes; fluoroquinolone antibiotic; pyrrolidinopiperidine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone	antibacterial drug
10-deacetylbaccatine iii 10-deacetylbaccatine III: structure given in first source	2.47	2	0	secondary alpha-hydroxy ketone; tetracyclic diterpenoid
hyoscyamine Hyoscyamine: The 3(S)-endo isomer of atropine.. (S)-atropine : An atropine with a 2S-configuration.	2.17	1	0	tropane alkaloid
schizandrin a schizandrin A: the major lignan, 2-9%, of Schisandra plant; has hepatoprotective, antioxidant, and antineoplastic activities	2.1	1	0
atractylenolide iii atractylenolide III: from Atractylodes macrocephala Koidz; structure in first source	2.21	1	0	naphthofuran	metabolite
ym 09151-2 nemonapride: structure in first source; RN given refers to compound with no isomeric designation. nemonapride : A racemate composed of (2S,3S)- and (2R,3R)-enantiomers of nemonapride. Highly potent dopamine D2-like receptor antagonist; selective over D1-like receptors (Ki values are 0.1 and 740 nM for D2-like and D1-like receptors respectively). Also potent 5-HT1A receptor agonist (IC50 = 34 nM) and has affinity for sigma receptors.. (2R,3R)-nemonapride : An optically active form of nemonapride having (2R,3R)-configuration.	2.03	1	0	N-(1-benzyl-2-methylpyrrolidin-3-yl)-5-chloro-2-methoxy-4-(methylamino)benzamide
naproxen Naproxen: An anti-inflammatory agent with analgesic and antipyretic properties. Both the acid and its sodium salt are used in the treatment of rheumatoid arthritis and other rheumatic or musculoskeletal disorders, dysmenorrhea, and acute gout.. naproxen : A methoxynaphthalene that is 2-methoxynaphthalene substituted by a carboxy ethyl group at position 6. Naproxen is a non-steroidal anti-inflammatory drug commonly used for the reduction of pain, fever, inflammation and stiffness caused by conditions such as osteoarthritis, kidney stones, rheumatoid arthritis, psoriatic arthritis, gout, ankylosing spondylitis, menstrual cramps, tendinitis, bursitis, and for the treatment of primary dysmenorrhea. It works by inhibiting both the COX-1 and COX-2 enzymes.	3.42	1	1	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
aethiopinone aethiopinone: structure in first source	2.15	1	0
hydroxyl radical Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.	5.8	6	1	oxygen hydride; oxygen radical; reactive oxygen species
triflimide triflimide: structure in first source	2.05	1	0
rhodioloside [no description available]	2.48	2	0	glycoside
indium trichloride indium trichloride: RN given refers to parent cpd	2.04	1	0
singlet oxygen Singlet Oxygen: An excited state of molecular oxygen generated photochemically or chemically. Singlet oxygen reacts with a variety of biological molecules such as NUCLEIC ACIDS; PROTEINS; and LIPIDS; causing oxidative damages.	7.71	19	1	chalcogen; monoatomic oxygen; nonmetal atom	macronutrient
peroxymonosulfate peroxymonosulfate: oxidizing agent in prevention of tooth discoloration; RN given refers to ion(2-)	4.9	1	1	sulfur oxide; sulfur oxoanion
neplanocin c neplanocin C: see also neplanocin A; structure in first source	2	1	0
cryptotanshinone cryptotanshinone: from Salvia miltiorrhiza	2.49	2	0	abietane diterpenoid	anticoronaviral agent
carbodiimides Carbodiimides: Compounds with the general formula RN=C=NR, where R is a hydrocarbyl group.. methanediimine : A carbodiimide in which both nitrogens are unsubstituted.	2.03	1	0	carbodiimide
cycloartane cycloartane : A triterpene that is lanostane in which there is a methylene bridge between the 5- and 9-positions.	2.05	1	0	triterpene
zinc hematoporphyrin [no description available]	2.03	1	0
secologanin (-)-secologanin : An iridoid monoterpenoid that is acetaldehyde in which on of the hydrogens of the methyl group has been replaced by a 2-(beta-D-glucopyranosyloxy)-3,4-dihydro-2H-pyran-4-yl group which is substituted at positions 3 and 5 by a vinyl and a methoxycarbonyl group, respectively (the 2S,3R,4S stereoisomer).	2.17	1	0	aldehyde; beta-D-glucoside; enoate ester; methyl ester; pyrans; secoiridoid glycoside	plant metabolite
strictosidine [no description available]	2.05	1	0	alkaloid ester; beta-D-glucoside; indole alkaloid; methyl ester
dhurrin dhurrin: cyanogenic glucoside from plant Sorghum; (R)-epimer is taxiphyllin; RN given refers to (S)-isomer; structure. (S)-4-hydroxymandelonitrile beta-D-glucoside : A beta-D-glucoside consisting of (S)-prunasin carrying a hydroxy substituent at position 4 on the phenyl ring.	2.58	2	0	beta-D-glucoside; cyanogenic glycoside; monosaccharide derivative; nitrile
capsidiol capsidiol: isolated from cultured cells of Nicotiana silvestris; structure given in first source. capsidiol : An eremophilane sesquiterpenoid that is (+)-5-epi-aristolochene bearing additional 1beta- and 3alpha-hydroxy substituents. It is a phytoalexin produced in Nicotiana and Capsicum plant species in response to pathogen attack.	3.12	5	0	eremophilane sesquiterpenoid; octahydronaphthalenes; sesquiterpene phytoalexin	antifungal agent; plant metabolite
momilactone a momilactone A: RN given for (3aR-(3aalpha,5aalpha,8beta,10abeta,10bbeta,10calpha))-isomer	4.23	5	0	diterpene lactone; pimarane diterpenoid
cyclodrine cyclodrine: structure	2.17	1	0	benzenes
glyceollin glyceollin: found in plants; structure	2.01	1	0	organic heteropentacyclic compound
sclareol sclareol: structure given in first source. sclareol : A labdane diterpenoid that is labd-14-ene substituted by hydroxy groups at positions 8 and 13. It has been isolated from Salvia sclarea.	2.73	3	0	labdane diterpenoid	antifungal agent; antimicrobial agent; apoptosis inducer; fragrance; plant metabolite
sdz wag-994 N(6)-cyclohexyl-2-O-methyladenosine: an A1-adenosine receptor agonist	1.99	1	0
2-hydroxy-3-methylvaleric acid 2-hydroxy-3-methylvaleric acid: RN given refers to cpd without isomeric designation. 2-hydroxy-3-methylpentanoic acid : A branched-chain fatty acid that is 3-methylpentanoic acid carrying a hydroxy substitutent at position 2.	2.06	1	0	2-hydroxy fatty acid; branched-chain fatty acid; short-chain fatty acid
fungitetraose nistose: structure in first source	2.25	1	0	oligosaccharide
trimethylsilyldiazomethane trimethylsilyldiazomethane: reagent for organic synthesis	2.45	2	0
amedin amedin: acetylcholine antagonist; RN given refers to parent cpd without isomeric designation; structure	2.02	1	0
cyclonerodiol cyclonerodiol: structure	2.11	1	0
threitol threitol: RN given refers to (R,R)-isomer. D-threitol : The D-enantiomer of threitol.	2.05	1	0	threitol	human metabolite
aminopterin Aminopterin: A folic acid derivative used as a rodenticide that has been shown to be teratogenic.	2.34	2	0	dicarboxylic acid	EC 1.5.1.3 (dihydrofolate reductase) inhibitor; mutagen
isopulegol isopulegol: isolated from Mentha cardiaca structure in first source	2.05	1	0	p-menthane monoterpenoid	metabolite
n,n'-bis(salicylideneamino)ethane-manganese(ii) N,N'-bis(salicylideneamino)ethane-manganese(II): structure given in first source	2.03	1	0
biotin vitamin B7 : Any member of a group of vitamers that belong to the chemical structural class called biotins that exhibit biological activity against vitamin B7 deficiency. Vitamin B7 deficiency is very rare in individuals who take a normal balanced diet. Foods rich in biotin are egg yolk, liver, cereals, vegetables (spinach, mushrooms) and rice. Symptoms associated with vitamin B7 deficiency include thinning hair, scaly skin rashes around eyes, nose and mouth, and brittle nails. The vitamers include biotin and its ionized and salt forms.	3.73	10	0	biotins; vitamin B7	coenzyme; cofactor; Escherichia coli metabolite; fundamental metabolite; human metabolite; mouse metabolite; nutraceutical; prosthetic group; Saccharomyces cerevisiae metabolite
angiotensin ii Giapreza: injectable form of angiotensin II used to increase blood pressure in adult patients with septic or other distributive shock. Ile(5)-angiotensin II : An angiotensin II that acts on the central nervous system (PDB entry: 1N9V).	4.96	12	0	amino acid zwitterion; angiotensin II	human metabolite
6-hydroxymellein [no description available]	2.25	1	0	isochromanes
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.	6.16	26	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.	7.08	57	0
sb 203580 [no description available]	2.08	1	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	2.11	1	0	diamino-1,3,5-triazine
organophosphonates hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.	4.02	14	0	divalent inorganic anion; phosphite ion
agelastatin a agelastatin A: structure in first source	2.72	3	0
cyclopentane-1,2-diamine cyclopentane-1,2-diamine: structure in first source	3.14	5	0
nickel monoxide [no description available]	2.21	1	0
melagatran [no description available]	2.03	1	0	azetidines; carboxamidine; dicarboxylic acid monoamide; non-proteinogenic alpha-amino acid; secondary amino compound	anticoagulant; EC 3.4.21.5 (thrombin) inhibitor; serine protease inhibitor
scutellarin scutellarin: see scutellarein for aglycone. scutellarin : The glycosyloxyflavone which is the 7-O-glucuronide of scutellarein.	2.11	1	0	glucosiduronic acid; glycosyloxyflavone; monosaccharide derivative; trihydroxyflavone	antineoplastic agent; proteasome inhibitor
botrydial botrydial: is produced in plant tissues infected by Botrytis cinerea; structure in first source. botrydial : A cytotoxic fungal metabolite isolated from plant tissues infected by phytopathogen Botrytis cinerea.	2.06	1	0	dialdehyde	mycotoxin
aflatoxin b1 Aflatoxin B1: A potent hepatotoxic and hepatocarcinogenic mycotoxin produced by the Aspergillus flavus group of fungi. It is also mutagenic, teratogenic, and causes immunosuppression in animals. It is found as a contaminant in peanuts, cottonseed meal, corn, and other grains. The mycotoxin requires epoxidation to aflatoxin B1 2,3-oxide for activation. Microsomal monooxygenases biotransform the toxin to the less toxic metabolites aflatoxin M1 and Q1.. aflatoxin B1 : An aflatoxin having a tetrahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h]chromene skeleton with oxygen functionality at positions 1, 4 and 11.	2.96	4	0	aflatoxin; aromatic ether; aromatic ketone	carcinogenic agent; human metabolite
glycitin glycitin: structure in first source. glycitin : A glycosyloxyisoflavone that is isoflavone substituted by a methoxy group at position 6, a hydroxy group at position 4' and a beta-D-glucopyranosyloxy group at position 7.	2.13	1	0	7-hydroxyisoflavones 7-O-beta-D-glucoside; hydroxyisoflavone; methoxyisoflavone; monosaccharide derivative	plant metabolite
4,8,12-trimethyl-1,3,7,11-tridecatetraene 4,8,12-trimethyl-1,3,7,11-tridecatetraene: released by lima bean plants upon predation by T. urticae	2.75	3	0
bd 1047 N-(2-(3,4-Dichlorphenyl)ethyl)-N,N',N'-trimethyl-1,2-ethandiamin: sigma receptor ligand; putative sigma receptor antagonist with antidystonic activity	2.73	3	0	primary amine
2'-deoxy cyclic amp [no description available]	1.96	1	0	3',5'-cyclic purine nucleotide	Saccharomyces cerevisiae metabolite
aphanorphine aphanorphine: isolated from the fresh water blue-green alga; structure in first source	2.01	1	0
n-acetylchitooctaose N-acetylchitooctaose: induces phytoalexin production in rice cells	2.07	1	0
erythritol 4-phosphate D-erythritol 4-phosphate : A tetritol phosphate consisting of D-erythritol having the phosphate at the 4-position.	2.21	1	0	alditol 4-phosphate; tetritol phosphate
n(delta)-acetylornithine N(delta)-acetylornithine: RN given refers to (L)-isomer. N(5)-acetyl-L-ornithine : An N(5)-acyl-L-ornithine in which the the acyl group is specified as acetyl.	2.06	1	0	acetyl-L-ornithine; N(5)-acetylornithine; N(5)-acyl-L-ornithine
pentafluorophenylmethacrylate pentafluorophenylmethacrylate: copolymerized with methylmethacrylate	2.17	1	0
thermospermine thermospermine: polyamine extracted from an extreme thermopile, Thermus thermophilus; structure. thermospermine : Propane-1,3-diamine in which a hydrogen attached to one nitrogen is substituted by a 3-aminoprop-1-yl group, and a hydrogen attached to the other nitrogen is substituted by a 4-aminobut-1-yl group. A polyamine natural product, its name arises from its similarity to spermine and the fact that it was first isolated from the extreme thermophile, Thermus thermophilus.	2.15	1	0	polyazaalkane; tetramine
4-anisoyl-3-(1,2,2-trimethylcyclopentane carboxylic acid) 4-anisoyl-3-(1,2,2-trimethylcyclopentane carboxylic acid): structure given in first source	1.96	1	0
fe(iii)-edta Fe(III)-EDTA: iron fortifying agent; RN given refers to parent cpd	2.01	1	0	iron coordination entity
coriolin coriolin: sesquiterpene antibiotic isolated from Coriolus consors; structure in third source	3.05	1	0
anabasine Anabasine: A piperidine botanical insecticide.. (S)-anabasine : The (S)-enantiomer of anabasine.. anabasine : A pyridine alkaloid that is pyridine substituted by a piperidin-2-yl group at position 3.	2.54	2	0	anabasine
bifeprunox bifeprunox: an antipsychotic agent	2.04	1	0	biphenyls
darunavir Darunavir: An HIV PROTEASE INHIBITOR that is used in the treatment of AIDS and HIV INFECTIONS. Due to the emergence of ANTIVIRAL DRUG RESISTANCE when used alone, it is administered in combination with other ANTI-HIV AGENTS.. darunavir : An N,N-disubstituted benzenesulfonamide bearing an unsubstituted amino group at the 4-position, used for the treatment of HIV infection. A second-generation HIV protease inhibitor, darunavir was designed to form robust interactions with the protease enzyme from many strains of HIV, including those from treatment-experienced patients with multiple resistance mutations to other protease inhibitors.	2.07	1	0	carbamate ester; furofuran; sulfonamide	antiviral drug; HIV protease inhibitor
eglumetad eglumetad: LY-354740 is the active isomer, LY-366563 is the inactive isomer, and LY 314582 is the racemate; structure given in first source	2.46	2	0	L-alpha-amino acid
sorafenib [no description available]	2.21	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
erythritol [no description available]	3.46	7	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.	2.03	1	0	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human blood serum metabolite
estradiol 3-benzoate 17beta-estradiol 3-benzoate : A benzoate ester resulting from the formal condensation of benzoic acid with the phenolic hydroxy group of 17beta-estradiol.	2.1	1	0	17beta-hydroxy steroid; benzoate ester	estrogen receptor agonist; xenoestrogen
fumagillol fumagillol: from Penicillium jensenii; FR 65814 is an analog; structure given in first source. fumagillol : A sesquiterpenoid with antimicrobial properties.	7.02	1	0	secondary alcohol; sesquiterpenoid; spiro-epoxide	antimicrobial agent
cortisone [no description available]	2.64	3	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
tenulin tenulin: toxic constituent of Helenium amarum (bitter sneezeweed); structure	2.38	2	0	sesquiterpene lactone
lilial [no description available]	2.44	2	0
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.	2.03	1	0	2-nitrophenols; C-nitro compound; nitrotyrosine; non-proteinogenic alpha-amino acid
5-hydroxymethylfurfural 5-hydroxymethylfurfural: has antisickling activity; HMF is the causative component in honey that affects the presystemic metabolism and pharmacokinetics of GZ in-vivo. 5-hydroxymethylfurfural : A member of the class of furans that is furan which is substituted at positions 2 and 5 by formyl and hydroxymethyl substituents, respectively. Virtually absent from fresh foods, it is naturally generated in sugar-containing foods during storage, and especially by drying or cooking. It is the causative component in honey that affects the presystemic metabolism and pharmacokinetics of GZ in-vivo.	2.87	3	0	arenecarbaldehyde; furans; primary alcohol	indicator; Maillard reaction product
propargylamine propargylamine: RN given refers to parent cpd; structure	2.08	1	0
lanosterol [no description available]	2.05	1	0	14alpha-methyl steroid; 3beta-sterol; tetracyclic triterpenoid	bacterial metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
2-chlorobiphenyl 2-chlorobiphenyl: RN from Toxlit. 2-chlorobiphenyl : A monochlorobiphenyl carrying a single chloro substituent at position 2.. monochlorobiphenyl : A chlorobiphenyl carrying a single chloro substituent at unspecified position.. chlorobiphenyl : A chloroarene that consists of a biphenyl skeleton substituted by one or more chloro groups.	2.04	1	0	monochlorobiphenyl
pheophorbide a pheophorbide a: split product of chlorophyll obtained by saponification of pheophytin	2.17	1	0
anisomycin Anisomycin: An antibiotic isolated from various Streptomyces species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system.. (-)-anisomycin : An antibiotic isolated from various Streptomyces species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system.	1.98	1	0	monohydroxypyrrolidine; organonitrogen heterocyclic antibiotic	anticoronaviral agent; antimicrobial agent; antineoplastic agent; antiparasitic agent; bacterial metabolite; DNA synthesis inhibitor; protein synthesis inhibitor
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	8	37	1
calendula Calendula: A plant genus of the family ASTERACEAE. Members contain CAROTENOIDS, essential oils (OILS, VOLATILE), flavonoids, mucilage, SAPONINS, and STEROLS. The plants are used both topically and internally. The common name of Marigold is also used for TAGETES.	2.21	1	0
withaferin a withaferin A: an antiestrogen and phytogenic antineoplastic agent isolated from leaves of Withania somnifera Dun.; structure. withaferin A : A withanolide that is 5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione substituted by hydroxy groups at positions 4 and 27 (the 4beta,5beta,6beta,22R stereoisomer). Isolated from Physalis longifolia, it exhibits cytotoxic activity.	2.79	3	0	27-hydroxy steroid; 4-hydroxy steroid; delta-lactone; enone; epoxy steroid; ergostanoid; primary alcohol; secondary alcohol; withanolide	antineoplastic agent; apoptosis inducer
fusicoccin fusicoccin: phytotoxic glycoside from Fusicoccum amydali; structure	2.06	1	0
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.	3.06	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]	1.99	1	0	isoxazoles; non-proteinogenic L-alpha-amino acid; organochlorine compound	antileishmanial agent; antimetabolite; antimicrobial agent; antineoplastic agent; EC 2.3.2.2 (gamma-glutamyltransferase) inhibitor; glutamine antagonist; metabolite
wortmannin [no description available]	2.92	4	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
2-oxindole 2-oxindole: RN given refers to parent cpd; structure. indolin-2-one : An indolinone carrying an oxo group at position 2.	3.33	6	0	gamma-lactam; indolinone
withanolides Withanolides: Ergostane derivatives of 28 carbons with oxygens at C1, C22, and C26 positions and the side chain cyclized. They are found in WITHANIA plant genus and have cytotoxic and other effects.	3.36	6	0
rocaglamide rocaglamide: RN refers to (1alpha,2alpha,3beta,3abeta,8bbeta)-isomer; isolated from stems of Aglaia elliptifolia; structure given in first source. rocaglamide : An organic heterotricyclic compound that is 2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan substituted by hydroxy groups at positions 1 and 8b, methoxy groups at positions 6 and 8, a 4-methoxyphenyl group at position 3a, a phenyl group at position 3 and a N,N-dimethylcarbamoyl group at position 1. Isolated from Aglaia odorata and Aglaia duperreana, it exhibits antineoplastic activity.	2.44	2	0	monocarboxylic acid amide; monomethoxybenzene; organic heterotricyclic compound	antileishmanial agent; antineoplastic agent; metabolite
trimethoprim, sulfamethoxazole drug combination Trimethoprim, Sulfamethoxazole Drug Combination: A drug combination with broad-spectrum antibacterial activity against both gram-positive and gram-negative organisms. It is effective in the treatment of many infections, including PNEUMOCYSTIS PNEUMONIA in AIDS.. co-trimoxazole : A two-component mixture comprising trimethoprim and sulfamethoxazole.	1.98	1	0
lobetyolin lobetyolin: from Herba Lobeliae Chinensis	2.21	1	0
sampangine sampangine: a plant-derived copyrine alkaloid extracted from the stem bark of Cananga odorata. sampangine : A copyrine alkaloid with formula C15H8N2O, extracted from several plants including the stem bark of Cananga odorata. It is a heme biosynthesis inhibitor and exhibits antifungal and anticancer properties.	2.15	1	0	alkaloid; organic heterotetracyclic compound	antifungal agent; plant metabolite
bortezomib [no description available]	3.36	6	0	amino acid amide; L-phenylalanine derivative; pyrazines	antineoplastic agent; antiprotozoal drug; protease inhibitor; proteasome inhibitor
n-methoxyindole-3-carbinol N-methoxyindole-3-carbinol: an inducer of cytochrome p-450 1A1 in cultured cells; a degradation product of 1-methyl-3-indolylmethyl glucosinolate; structure in first source	2.08	1	0
dihydropyridines Dihydropyridines: Pyridine moieties which are partially saturated by the addition of two hydrogen atoms in any position.	2.93	4	0
germine germine: alkamine; present in many polyester alkaloids which occur in Veratrum & Zydadenus species; may be used medically as an antihypertensive agent; minor descriptor (75-83); on-line & Index Medicus search CEVANES (75-83); RN given refers to parent cpd; structure	2.49	2	0
3-aminocyclopentane-1-carboxylic acid 3-aminocyclopentane-1-carboxylic acid: structure given in first source; a selective GABA-A agonist; a cyclopentane analog of GABA; RN given for (trans)-isomer	4.79	10	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.	4.4	21	0
carboplatin [no description available]	4.2	3	1
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.	1.98	1	0	inorganic chloride; lithium salt	antimanic drug; geroprotector
s-adenosylhomocysteine S-Adenosylhomocysteine: 5'-S-(3-Amino-3-carboxypropyl)-5'-thioadenosine. Formed from S-adenosylmethionine after transmethylation reactions.. S-adenosyl-L-homocysteine : An organic sulfide that is the S-adenosyl derivative of L-homocysteine.	2.03	1	0	adenosines; amino acid zwitterion; homocysteine derivative; homocysteines; organic sulfide	cofactor; EC 2.1.1.72 [site-specific DNA-methyltransferase (adenine-specific)] inhibitor; EC 2.1.1.79 (cyclopropane-fatty-acyl-phospholipid synthase) inhibitor; epitope; fundamental metabolite
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.	2.37	2	0
sorbose sorbopyranose : The pyranose form of sorbose.. L-sorbopyranose : The L-stereoisomer of sorbopyranose.	2.13	1	0	L-sorbose; sorbopyranose
arabinose [no description available]	2.39	2	0	L-arabinose	Escherichia coli metabolite; mouse metabolite
n-acetylneuraminic acid N-Acetylneuraminic Acid: An N-acyl derivative of neuraminic acid. N-acetylneuraminic acid occurs in many polysaccharides, glycoproteins, and glycolipids in animals and bacteria. (From Dorland, 28th ed, p1518). N-acetylneuraminic acid : An N-acylneuraminic acid where the N-acyl group is specified as acetyl.	3.61	9	0	N-acetylneuraminic acids	antioxidant; bacterial metabolite; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor; human metabolite; mouse metabolite
mannose-6-phosphate beta-D-mannose 6-phosphate : A D-mannopyranose 6-phosphate with a beta-configuration at the anomeric position.	2.67	3	0	D-mannopyranose 6-phosphate
fibrin Fibrin: A protein derived from FIBRINOGEN in the presence of THROMBIN, which forms part of the blood clot.	1.94	1	0	peptide
bradykinin [no description available]	3.22	6	0	oligopeptide	human blood serum metabolite; vasodilator agent
canavanine L-canavanine : A non-proteinogenic L-alpha-amino acid that is L-homoserine substituted at oxygen with a guanidino (carbamimidamido) group. Although structurally related to L-arginine, it is non-proteinogenic.	1.98	1	0	amino acid zwitterion; non-proteinogenic L-alpha-amino acid	phytogenic insecticide; plant metabolite
hexacyanoferrate iii hexacyanoferrate III: RN given refers to parent cpd	2.01	1	0
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.	3.6	9	0	D-glucosamine	Escherichia coli metabolite; geroprotector; mouse metabolite
polygalacturonic acid galacturonic acid: N1 same as NM; RN given refers to parent cpd with unspecified isomeric designation. D-galactopyranuronic acid : The pyranose form of D-galacturonic acid. D-galacturonic acid : The D-enantiomer of galacturonic acid. It is the main component of pectin.	2.46	2	0	D-galacturonic acid
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.	5.11	14	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.	2.42	2	0	raffinose family oligosaccharide; trisaccharide	mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
naringenin (S)-naringenin : The (S)-enantiomer of naringenin.	3.25	5	0	(2S)-flavan-4-one; naringenin	expectorant; plant metabolite
epiglucan epiglucan: a highly side-chain/branched alkali-insoluble cell wall glucan from fungus such as Epicoccum nigrum, Botrytis cinerea, ascomycetes & basidiomycetes; also isolated S-4001 from Lei Wan (polyporus mylitiae), HA-beta-glucan from mushroom Pleutotus ostreatus (Fr.) Quel., and translam from seaweed Laminaria cichorioides; with commercially important functional properties including emulsification and friction reduction.	2.75	3	0
oxytocin Oxytocin: A nonapeptide hormone released from the neurohypophysis (PITUITARY GLAND, POSTERIOR). It differs from VASOPRESSIN by two amino acids at residues 3 and 8. Oxytocin acts on SMOOTH MUSCLE CELLS, such as causing UTERINE CONTRACTIONS and MILK EJECTION.. oxytocin : A cyclic nonapeptide hormone with amino acid sequence CYIQNCPLG that also acts as a neurotransmitter in the brain; the principal uterine-contracting and milk-ejecting hormone of the posterior pituitary. Together with the neuropeptide vasopressin, it is believed to influence social cognition and behaviour.	2.89	1	0	heterodetic cyclic peptide; peptide hormone	oxytocic; vasodilator agent
theanine theanine: RN given refers to (L)-isomer; precursor of ethylamine; found in green tea. N(5)-ethyl-L-glutamine : A N(5)-alkylglutamine where the alkyl group is ethyl. It has been isolated from green tea.	2.21	1	0	amino acid zwitterion; N(5)-alkyl-L-glutamine	geroprotector; neuroprotective agent; plant metabolite
7-dehydrocholesterol [no description available]	2.04	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; cholestanoid; Delta(5),Delta(7)-sterol	human metabolite; mouse metabolite
inositol 1,4,5-trisphosphate Inositol 1,4,5-Trisphosphate: Intracellular messenger formed by the action of phospholipase C on phosphatidylinositol 4,5-bisphosphate, which is one of the phospholipids that make up the cell membrane. Inositol 1,4,5-trisphosphate is released into the cytoplasm where it releases calcium ions from internal stores within the cell's endoplasmic reticulum. These calcium ions stimulate the activity of B kinase or calmodulin.	3.25	6	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.	3.58	9	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
salicin [no description available]	2.15	1	0	aromatic primary alcohol; aryl beta-D-glucoside; benzyl alcohols	antipyretic; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; prodrug
scopolin [no description available]	2.1	1	0	beta-D-glucoside; coumarins; monosaccharide derivative	plant metabolite
puromycin [no description available]	5.47	8	0	puromycins	antiinfective agent; antimicrobial agent; antineoplastic agent; EC 3.4.11.14 (cytosol alanyl aminopeptidase) inhibitor; EC 3.4.14.2 (dipeptidyl-peptidase II) inhibitor; nucleoside antibiotic; protein synthesis inhibitor
tosylphenylalanyl chloromethyl ketone Tosylphenylalanyl Chloromethyl Ketone: An inhibitor of Serine Endopeptidases. Acts as alkylating agent and is known to interfere with the translation process.. N-tosyl-L-phenylalanyl chloromethyl ketone : The N-tosyl derivative of L-phenylalanyl chloromethyl ketone.	1.98	1	0	alpha-chloroketone; sulfonamide	alkylating agent; serine proteinase inhibitor
tartaric acid tartaric acid: RN given refers to cpd with unspecified isomeric designation. D-tartaric acid : The D-enantiomer of tartaric acid.	2.51	2	0	tartaric acid	Escherichia coli 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.	2.02	1	0	guanidines; L-arginine derivative; N-nitro compound; non-proteinogenic L-alpha-amino acid
mannosamine mannosamine: RN given refers to parent cpd without isomeric designation. D-mannosamine : The D-enantiomer of mannosamine.. 2-amino-2-deoxy-D-mannopyranose : A D-mannosamine in cyclic pyranose form.	2.4	2	0	D-mannosamine
homoglutathione [no description available]	2.48	2	0	gamma-glutamylcysteine
dehydroascorbic acid Dehydroascorbic Acid: The reversibly oxidized form of ascorbic acid. It is the lactone of 2,3-DIKETOGULONIC ACID and has antiscorbutic activity in man on oral ingestion.. L-dehydroascorbate : An organic anion and the conjugate base of L-dehydroascorbic acid, arising from deprotonation of the acidic C2-position.. L-dehydroascorbic acid : Dehydroascorbic acid having the L-configuration.	1.97	1	0	dehydroascorbic acid; vitamin C	coenzyme; mouse metabolite
eriodictyol eriodictyol: structure. eriodictyol : A tetrahydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5, 7, 3' and 4' respectively.	2.13	1	0	3'-hydroxyflavanones; tetrahydroxyflavanone
fructans (2->6)-beta-D-fructan : A fructan compound consisting of repeating (2->6)-beta-linked fructofuranose units.	2.79	3	0
cellulase Cellulase: An endocellulase with specificity for the hydrolysis of 1,4-beta-glucosidic linkages in CELLULOSE, lichenin, and cereal beta-glucans.. beta-cellotriose : A cellotriose with a beta-configuration at the anomeric position.	3.53	8	0	cellotriose
strychnine Strychnine: An alkaloid found in the seeds of STRYCHNOS NUX-VOMICA. It is a competitive antagonist at glycine receptors and thus a convulsant. It has been used as an analeptic, in the treatment of nonketotic hyperglycinemia and sleep apnea, and as a rat poison.. strychnine : A monoterpenoid indole alkaloid that is strychnidine bearing a keto substituent at the 10-position.	2.66	3	0	monoterpenoid indole alkaloid; organic heteroheptacyclic compound	avicide; cholinergic antagonist; glycine receptor antagonist; neurotransmitter agent; rodenticide
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.	3.95	2	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.	9.42	93	0	cyclic hemiketal; monocarboxylic acid; polyether antibiotic; spiroketal	antifungal agent; coccidiostat; ionophore
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.	2.4	2	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.	1.98	1	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)	3.39	7	0	benzazocine
hyperforin hyperforin: a prenylated acylphloroglucinol derivative; antibiotic component of novoimanine; psychoactive agent in St. John's wort; Russian; structure;. hyperforin : A cyclic terpene ketone that is a prenylated carbobicyclic acylphloroglucinol derivative produced by St. John's Wort, Hypericum perforatum.	2.03	1	0
abacavir abacavir: a carbocyclic nucleoside with potent selective anti-HIV activity. abacavir : A 2,6-diaminopurine that is (1S)-cyclopent-2-en-1-ylmethanol in which the pro-R hydrogen at the 4-position is substituted by a 2-amino-6-(cyclopropylamino)-9H-purin-9-yl group. A nucleoside analogue reverse transcriptase inhibitor (NRTI) with antiretroviral activity against HIV, it is used (particularly as the sulfate) with other antiretrovirals in combination therapy of HIV infection.	2.13	1	0	2,6-diaminopurines	antiviral drug; drug allergen; HIV-1 reverse transcriptase inhibitor
ginsenoside rg1 [no description available]	2.48	2	0	12beta-hydroxy steroid; 3beta-hydroxy-4,4-dimethylsteroid; beta-D-glucoside; ginsenoside; tetracyclic triterpenoid	neuroprotective agent; pro-angiogenic agent
beta-hederin beta-hederin: derived from beta-amyrin; other hederigenin based saponins are available	2.05	1	0	triterpenoid
brucine brucine: was heading 1991-94 (see under STRYCHNINE 1975-90); DIMETHOXYSTRYCHNINE was see BRUCINE 1975-94; use STRYCHNINE to search BRUCINE 1975-94; very toxic alkaloid from Nux vomica similar to strychnine; used as reagent in analytical chemistry; was MH 1991-94	1.98	1	0	monoterpenoid indole alkaloid; organic heteroheptacyclic compound
patchouli alcohol patchouli alcohol: major component of the essential oil of patchouli; perfumery raw material. patchouli alcohol : A carbotricyclic compound and sesquiterpenoid tertiary alcohol that is tricyclo[5.3.1.0(3,8)]undecan-3-ol which is substituted at positions 2, 2, 6 and 8 by methyl groups (the 1R,3R,6S,7S,8S-diastereoisomer).	2.61	2	0
dolichodial dolichodial: isolated from walkingstick, Anisomorpha buprestoides. dolichodial : A dialdehyde that is cyclopentanecarbaldehyde substituted by a methyl group at position 2 and a 3-oxo-prop-1-en-2yl group at position 5. It has been found to occur in pheromones of insects such as aphids.	2.04	1	0	dialdehyde; iridoid monoterpenoid; olefinic compound	animal metabolite; plant metabolite; volatile oil component
swertiamarin swertiamarin: seco-iridoid glucoside from Swertia japonica;	2.05	1	0	glycoside
phenylpropanolamine fawcettimine: from Lyopodium; structure in first source	2.06	1	0	azaspiro compound
pulegone pulegone: component of peppermint oil; RN given refers to cpd without isomeric designation; structure in Merck. (+)-pulegone : The (5R)-enantiomer of p-menth-4(8)-en-3-one.	2	1	0	p-menth-4(8)-en-3-one
ochratoxin a ochratoxin A: structure in first source & in Merck, 9th ed, #6549. ochratoxin A : A phenylalanine derivative resulting from the formal condensation of the amino group of L-phenylalanine with the carboxy group of (3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carboxylic acid (ochratoxin alpha). It is among the most widely occurring food-contaminating mycotoxins, produced by Aspergillus ochraceus, Aspergillus carbonarius and Penicillium verrucosum.	2.11	1	0	isochromanes; monocarboxylic acid amide; N-acyl-L-phenylalanine; organochlorine compound; phenylalanine derivative	Aspergillus metabolite; calcium channel blocker; carcinogenic agent; mycotoxin; nephrotoxin; Penicillium metabolite; teratogenic agent
alpha bitter acid humulon: antibiotic from hops; structure	2.42	2	0	aromatic ketone; cyclic ketone; diketone; tertiary alpha-hydroxy ketone; triol	antibacterial drug; antioxidant; cyclooxygenase 2 inhibitor; metabolite
littorine littorine: RN given refers to (3(R)-endo)-isomer; RN for cpd without isomeric designation not avail 3/90; isolated from a Duboisia hybrid	2.07	1	0	tropane alkaloid
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)	4.98	11	0
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.	2.9	4	0	aldehyde; tripeptide	cysteine protease inhibitor
2-c-methylerythritol 4-phosphate 2-C-methylerythritol 4-phosphate: structure in first source	3.16	5	0	tetritol phosphate	Escherichia coli metabolite
n-formylmethionine leucyl-phenylalanine N-Formylmethionine Leucyl-Phenylalanine: A formylated tripeptide originally isolated from bacterial filtrates that is positively chemotactic to polymorphonuclear leucocytes, and causes them to release lysosomal enzymes and become metabolically activated.. N-formyl-L-methionyl-L-leucyl-L-phenylalanine : A tripeptide composed of L-Met, L-Leu and L-Phe in a linear sequence with a formyl group at the amino terminus. It acts as a potent inducer of leucocyte chemotaxis and macrophage activator as well as a ligand for the FPR receptor.	2.9	4	0	tripeptide
candoxatrilat candoxatrilat: USAN lists candoxatrilat (UK-73,967) with RN 123122-54-3. candoxatrilat : A dicarboxylic acid monoamide obtained by formal condensation between the amino group of cis-4-aminocyclohexanecarboxylic acid and the cyclopentanecarboxylic acid group of 1-[(2S)-2-carboxy-3-(2-methoxyethoxy)propyl]cyclopentanecarboxylic acid. A potent inhibitor of neutral endopeptidase (NEP, neprilysin, EC 3.4.24.11), it is used as its 2,3-dihydro-1H-inden-5-yl ester prodrug in the treatment of chronic heart failure.	1.98	1	0
plasminogen activator inhibitor 2 N-butyrylhomoserine lactone: quorum sensing compound biosynthesized by LasI protein; structure given in first source	2.03	1	0	N-acyl-amino acid
sodium arsenite sodium arsenite : An inoganic sodium salt with formula with formula NaAsO2.	2.41	2	0	arsenic molecular entity; inorganic sodium salt	antibacterial agent; antifungal agent; antineoplastic agent; carcinogenic agent; herbicide; insecticide; rodenticide
actinonin actinonin: natural hydroxamic acid, pseudopeptide antibiotic isolated from Streptomyces species; structure	2.05	1	0
soyasaponin ii soyasaponin II: isolated from the soybean Glycine max; RN given for (3beta,4beta,22beta)-isomer	2.01	1	0	triterpenoid saponin
validamycin a validamycin A : A member of the class of validamycins that is (1R,2S,3S,4S,6R)-4-amino-6-(hydroxymethyl)cyclohexane-1,2,3-triol in which the hydroxy group at position 1 has been converted to its beta-D-glucoside and in which one of the hydrogens attached to the nitrogen is replaced by a (1R,4R,5R,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl group. It is the major validamycin produced by Streptomyces hygroscopicus.	2.25	1	0	antibiotic fungicide; polyol; secondary amino compound; validamycins	antifungal agrochemical; EC 2.4.1.231 [alpha,alpha-trehalose phosphorylase (configuration-retaining)] inhibitor; EC 2.4.1.64 (alpha,alpha-trehalose phosphorylase) inhibitor; EC 3.2.1.28 (alpha,alpha-trehalase) inhibitor
malvidin-3-glucoside malvidin 3-O-beta-D-glucoside : An anthocyanin cation consisting of malvidin having a beta-D-glucosyl residue attached at the 3-hydroxy position.	2.01	1	0	anthocyanin cation; aromatic ether; beta-D-glucoside	metabolite
eplerenone Eplerenone: A spironolactone derivative and selective ALDOSTERONE RECEPTOR antagonist that is used in the management of HYPERTENSION and CONGESTIVE HEART FAILURE, post-MYOCARDIAL INFARCTION.	2.25	1	0	3-oxo-Delta(4) steroid; epoxy steroid; gamma-lactone; methyl ester; organic heteropentacyclic compound; oxaspiro compound; steroid acid ester	aldosterone antagonist; antihypertensive agent
amcinonide amcinonide: structure	3.34	1	1	11beta-hydroxy steroid; 20-oxo steroid; 3-oxo-Delta(1),Delta(4)-steroid; acetate ester; corticosteroid; fluorinated steroid; spiroketal	anti-inflammatory drug
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	4.27	17	0	cyclodextrin
acetyl coenzyme a Acetyl Coenzyme A: Acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent.	2.47	2	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	3.51	8	0	cinnamic acid	plant metabolite
ergosterol [no description available]	3.3	6	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; ergostanoid; phytosterols	fungal metabolite; Saccharomyces cerevisiae metabolite
tretinoin Tretinoin: An important regulator of GENE EXPRESSION during growth and development, and in NEOPLASMS. Tretinoin, also known as retinoic acid and derived from maternal VITAMIN A, is essential for normal GROWTH; and EMBRYONIC DEVELOPMENT. An excess of tretinoin can be teratogenic. It is used in the treatment of PSORIASIS; ACNE VULGARIS; and several other SKIN DISEASES. It has also been approved for use in promyelocytic leukemia (LEUKEMIA, PROMYELOCYTIC, ACUTE).. retinoic acid : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraenoic acid substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).. all-trans-retinoic acid : A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry.	4.78	7	1	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.	5.58	22	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
farnesol Farnesol: A colorless liquid extracted from oils of plants such as citronella, neroli, cyclamen, and tuberose. It is an intermediate step in the biological synthesis of cholesterol from mevalonic acid in vertebrates. It has a delicate odor and is used in perfumery. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). (2-trans,6-trans)-farnesol : The (2-trans,6-trans)-stereoisomer of farnesol.. farnesol : A farnesane sesquiterpenoid that is dodeca-2,6,10-triene substituted by methyl groups at positions 3, 7 and 11 and a hydroxy group at position 1.	2.77	3	0	farnesol	plant metabolite
phosphoramidon phosphoramidon: a membrane metallo-endopeptidase & endothelin-converting enzyme inhibitor; thermolysin inhibitor from culture filtrate of Streptomyces tanashiensis; structure. phosphoramidon : A dipeptide isolated from the cultures of Streptomyces tanashiensis.	1.98	1	0	deoxyaldohexose phosphate; dipeptide	bacterial metabolite; EC 3.4.24.11 (neprilysin) inhibitor; EC 3.4.24.71 (endothelin-converting enzyme 1) inhibitor
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.	3.16	5	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.	4.66	25	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).	2.66	3	0	retinol; vitamin A	human metabolite; mouse metabolite; plant metabolite
palmitoleic acid hexadecenoate : A long-chain unsaturated fatty acid anion that is the conjugate base of hexadecenoic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.	2.13	1	0	hexadec-9-enoic acid	algal metabolite; Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; Escherichia coli metabolite; human blood serum metabolite
oleic acid Oleic Acid: An unsaturated fatty acid that is the most widely distributed and abundant fatty acid in nature. It is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. (Stedman, 26th ed). oleic acid : An octadec-9-enoic acid in which the double bond at C-9 has Z (cis) stereochemistry.	3.61	9	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.	1.99	1	0	macrolide lactam	bacterial metabolite; immunosuppressive agent
farnesyl pyrophosphate farnesyl pyrophosphate: a sesquiterpene that dimerizes to SQUALENE; RN given refers to cpd without isomeric designation. 2-trans,6-trans-farnesyl diphosphate : The trans,trans-stereoisomer of farnesyl diphosphate.	3.75	10	0	farnesyl diphosphate	Escherichia coli metabolite; mouse metabolite
ferulic acid ferulate : A monocarboxylic acid anion obtained by the deprotonation of the carboxy group of ferulic acid.	3.48	7	0	ferulic acids	anti-inflammatory agent; antioxidant; apoptosis inhibitor; cardioprotective agent; MALDI matrix material; plant metabolite
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.	5.19	14	0	D-galactopyranuronic acid
geranyl pyrophosphate geranyl pyrophosphate: RN given refers to (E)-isomer. geranyl diphosphate : The diphosphate of the polyprenol compound geraniol.	3.17	5	0	polyprenyl diphosphate	Escherichia coli metabolite; mouse metabolite
cocaine Cocaine: An alkaloid ester extracted from the leaves of plants including coca. It is a local anesthetic and vasoconstrictor and is clinically used for that purpose, particularly in the eye, ear, nose, and throat. It also has powerful central nervous system effects similar to the amphetamines and is a drug of abuse. Cocaine, like amphetamines, acts by multiple mechanisms on brain catecholaminergic neurons; the mechanism of its reinforcing effects is thought to involve inhibition of dopamine uptake.. cocaine : A tropane alkaloid obtained from leaves of the South American shrub Erythroxylon coca.	3.92	13	0	benzoate ester; methyl ester; tertiary amino compound; tropane alkaloid	adrenergic uptake inhibitor; central nervous system stimulant; dopamine uptake inhibitor; environmental contaminant; local anaesthetic; mouse metabolite; plant metabolite; serotonin uptake inhibitor; sodium channel blocker; sympathomimetic agent; vasoconstrictor agent; xenobiotic
eicosapentaenoic acid icosapentaenoic acid : Any straight-chain, C20 polyunsaturated fatty acid having five C=C double bonds.. all-cis-5,8,11,14,17-icosapentaenoic acid : An icosapentaenoic acid having five cis-double bonds at positions 5, 8, 11, 14 and 17.	2.8	3	0	icosapentaenoic acid; omega-3 fatty acid	anticholesteremic drug; antidepressant; antineoplastic agent; Daphnia galeata metabolite; fungal metabolite; micronutrient; mouse metabolite; nutraceutical
thapsigargin Thapsigargin: A sesquiterpene lactone found in roots of THAPSIA. It inhibits SARCOPLASMIC RETICULUM CALCIUM-TRANSPORTING ATPASES.. thapsigargin : An organic heterotricyclic compound that is a hexa-oxygenated 6,7-guaianolide isolated fron the roots of Thapsia garganica L., Apiaceae. A potent skin irritant, it is used in traditional medicine as a counter-irritant. Thapsigargin inhibits Ca(2+)-transporting ATPase mediated uptake of calcium ions into sarcoplasmic reticulum and is used in experimentation examining the impacts of increasing cytosolic calcium concentrations.	3.51	8	0	butyrate ester; organic heterotricyclic compound; sesquiterpene lactone	calcium channel blocker; EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor
brivudine brivudine: anti-herpes agent	2.38	2	0
lycopene [no description available]	2.52	2	0	acyclic carotene	antioxidant; plant metabolite
fosfomycin Fosfomycin: An antibiotic produced by Streptomyces fradiae.. fosfomycin : A phosphonic acid having an (R,S)-1,2-epoxypropyl group attached to phosphorus.	2.44	2	0	epoxide; phosphonic acids	antimicrobial agent; EC 2.5.1.7 (UDP-N-acetylglucosamine 1-carboxyvinyltransferase) inhibitor
geranylgeranyl pyrophosphate geranylgeranyl pyrophosphate: RN given refers to (E,E,E)-isomer. geranylgeranyl diphosphate : A polyprenol diphosphate having geranylgeranyl as the polyprenyl component.. 2-trans,6-trans,10-trans-geranylgeranyl diphosphate : The all-trans-isomer of geranylgeranyl diphosphate.	3.19	5	0	geranylgeranyl diphosphate	mouse metabolite
2-butenal crotonaldehyde : An enal consisting of propene having a formyl group at the 1-position.	2.02	1	0	enal
neocarzinostatin chromophore neocarzinostatin chromophore: nonprotein chromophore of neocarzinostatin; antibiotic activity of Neocarzinostatin depends on wholy on chromophore interaction with DNA; Chrom A & Chrom B are separated by HPLC; Chrom C is derived from Chrom A; Chrom D is inactive minor component. neocarzinostatin chromophore : A naphthoate ester obtained by formal condensation of the carboxy group of 2-hydroxy-7-methoxy-5-methyl-1-naphthoic acid with the 5-hydroxy group of (1aS,5R,6R,6aE,9aR)-5-hydroxy-1a-[(4R)-2-oxo-1,3-dioxolan-4-yl]-2,3,8,9-tetradehydro-1a,5,6,9a-tetrahydrocyclopenta[5,6]cyclonona[1,2-b]oxiren-6-yl 2,6-dideoxy-2-(methylamino)-alpha-D-galactopyranoside. The chromophoric part of neocarzinostatin, it is tightly and non-covelently bound to a 113-membered apoprotein, which serves to protect it and release it to the target DNA.	2.01	1	0	cyclopentacyclononaoxirene; D-galactosaminide; dioxolane; monosaccharide derivative; naphthoate ester	antineoplastic agent
isofagomine [no description available]	2.25	1	0	piperidines
phenylalanyl-prolyl-arginine [no description available]	2.01	1	0	oligopeptide
cytidine monophosphate n-acetylneuraminic acid Cytidine Monophosphate N-Acetylneuraminic Acid: A nucleoside monophosphate sugar which donates N-acetylneuraminic acid to the terminal sugar of a ganglioside or glycoprotein.. CMP-N-acetyl-beta-neuraminic acid : A nucleotide sugar used as a donor by glycosyltransferases for the synthesis of sugar chains	2.39	2	0	CMP-N-acyl-beta-neuraminic acid	mouse metabolite
prostaglandin d2 Prostaglandin D2: The principal cyclooxygenase metabolite of arachidonic acid. It is released upon activation of mast cells and is also synthesized by alveolar macrophages. Among its many biological actions, the most important are its bronchoconstrictor, platelet-activating-factor-inhibitory, and cytotoxic effects.. prostaglandin D2 : A member of the class of prostaglandins D that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9 and 15 and an oxo group at position 11 (the 5Z,9alpha,13E,15S- stereoisomer).	6.89	51	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.	2.66	3	0	olefinic compound; polyphenol	antifungal agent; antineoplastic agent; autophagy inducer; calcium channel blocker; carcinogenic agent; EC 1.1.1.146 (11beta-hydroxysteroid dehydrogenase) inhibitor; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; endocrine disruptor; xenoestrogen
zeatin Zeatin: An aminopurine factor in plant extracts that induces cell division. (Grant & Hackh's Chemical Dict, 5th ed)	3.44	7	0	zeatin	plant metabolite
alitretinoin Alitretinoin: A retinoid that is used for the treatment of chronic hand ECZEMA unresponsive to topical CORTICOSTEROIDS. It is also used to treat cutaneous lesions associated with AIDS-related KAPOSI SARCOMA.	2.05	1	0	retinoic acid	antineoplastic agent; keratolytic drug; metabolite; retinoid X receptor agonist
h 89 N-(2-(4-bromocinnamylamino)ethyl)-5-isoquinolinesulfonamide: structure given in first source. N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide : A member of the class of isoquinolines that is the sulfonamide obtained by formal condensation of the sulfo group of isoquinoline-5-sulfonic acid with the primary amino group of N(1)-[3-(4-bromophenyl)prop-2-en-1-yl]ethane-1,2-diamine. It is a protein kinase A inhibitor.. (E)-N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide : A N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide in which the double bond adopts a trans-configuration.	2.71	3	0	N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide
gs 4071 GS 4071: The acid form.. oseltamivir acid : A cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid which is substituted at positions 3, 4, and 5 by pentan-3-yloxy, acetamido, and amino groups, respectively (the 3R,4R,5S enantiomer). An antiviral drug, it is used as the corresponding ethyl ester prodrug, oseltamivir, to slow the spread of influenza.	3.01	4	0	acetate ester; amino acid; cyclohexenecarboxylic acid; primary amino compound	antiviral drug; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor; marine xenobiotic metabolite
afimoxifene afimoxifene : A tertiary amino compound that is tamoxifen in which the phenyl group which is in a Z- relationship to the ethyl substituent is hydroxylated at the para- position. It is the active metabolite of tamoxifen.	2.07	1	0	phenols; tertiary amino compound	antineoplastic agent; estrogen receptor antagonist; metabolite
imidazolidines [no description available]	3	4	0	azacycloalkane; imidazolidines; saturated organic heteromonocyclic parent
phorbol-12,13-didecanoate phorbol-12,13-didecanoate: RN given refers to (1aR-(1a alpha,1b beta,4a beta,7a alpha,7b alpha,8 alpha,9 beta,9a alpha))-isomer	1.98	1	0
texas red Texas red: hydrophilic Texas red; structure given in first source	2.39	2	0	organic heteroheptacyclic compound	fluorochrome
steviol steviol: aglucon of stevioside; RN given refers to (4alpha)-isomer. steviol : An ent-kaurane diterpenoid that is 5beta,8alpha,9beta,10alpha-kaur-16-en-18-oic acid in which the hydrogen at position 13 has been replaced by a hydroxy group.	2.06	1	0	bridged compound; ent-kaurane diterpenoid; monocarboxylic acid; tertiary allylic alcohol; tetracyclic diterpenoid	antineoplastic agent
iridoids Iridoids: A type of MONOTERPENES, derived from geraniol. They have the general form of cyclopentanopyran, but in some cases, one of the rings is broken as in the case of secoiridoid. They are different from the similarly named iridals (TRITERPENES).	6.64	15	1
laminaran laminaran: beta-1,3-glucan	2.1	1	0
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)	5.07	14	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.	2.01	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; phytosterols	marine metabolite; plant metabolite
bevirimat bevirimat: an HIV inhibitor; disrupts late step in processing HIV Major Core Protein p24, preventing the capsid precursor p25 from being converted to mature capsid p24. bevirimat : A pentacyclic triterpenoid obtained by the formal condensation of 2,2-dimethylsuccinic acid with the 3-hydroxy group of betulinic acid. It is isolated from the Chinese herb Syzygium claviflorum. The first in the class of HIV-1 maturation inhibitors to be studied in humans, bevirimat was identified as a potent HIV drug candidate and several clinical trials were conducted, but development into a new drug was plagued by numerous resistance-related problems.	2.05	1	0	dicarboxylic acid monoester; monocarboxylic acid; pentacyclic triterpenoid	HIV-1 maturation inhibitor; metabolite
tiazofurin tiazofurin: RN given refers to (beta-D)-isomer; structure given in first source. tiazofurine : A C-glycosyl compound that is 1,3-thiazole-4-carboxamide in which the hydrogen at position 2 has been replaced by a beta-D-ribofuranosyl group. It is metabolised to thiazole-4-carboxamide adenine dinucleotide (TAD), a selective inhibitor of inosine monophosphate dehydrogenase (IMP dehydrogenase).	1.98	1	0	1,3-thiazoles; C-glycosyl compound; monocarboxylic acid amide	antineoplastic agent; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; prodrug
aphidicolin Aphidicolin: An antiviral antibiotic produced by Cephalosporium aphidicola and other fungi. It inhibits the growth of eukaryotic cells and certain animal viruses by selectively inhibiting the cellular replication of DNA polymerase II or the viral-induced DNA polymerases. The drug may be useful for controlling excessive cell proliferation in patients with cancer, psoriasis or other dermatitis with little or no adverse effect upon non-multiplying cells.. aphidicolin : A tetracyclic diterpenoid that has an tetradecahydro-8,11a-methanocyclohepta[a]naphthalene skeleton with two hydroxymethyl substituents at positions 4 and 9, two methyl substituents at positions 4 and 11b and two hydroxy substituents at positions 3 and 9. An antibiotic with antiviral and antimitotical properties. Aphidicolin is a reversible inhibitor of eukaryotic nuclear DNA replication.	2.93	4	0	tetracyclic diterpenoid	antimicrobial agent; antimitotic; antineoplastic agent; antiviral drug; apoptosis inducer; Aspergillus metabolite; DNA synthesis inhibitor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; fungal metabolite
carbodine carbodine: RN given refers to (R-(1alpha,2beta,3beta,4alpha))-isomer	2.77	3	0
azaserine Azaserine: Antibiotic substance produced by various Streptomyces species. It is an inhibitor of enzymatic activities that involve glutamine and is used as an antineoplastic and immunosuppressive agent.. azaserine : A carboxylic ester resulting from the formal condensation of the carboxy group of diazoacetic acid with the alcoholic hydroxy group of L-serine. An antibiotic produced by a Streptomyces species.	3.44	2	0	carboxylic ester; diazo compound; L-serine derivative; non-proteinogenic L-alpha-amino acid	antifungal agent; antimetabolite; antimicrobial agent; antineoplastic agent; glutamine antagonist; immunosuppressive agent; metabolite
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.	2.41	2	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.	3.54	8	0	amino aldehyde; carbamate ester; tripeptide	proteasome inhibitor
tenofovir tenofovir (anhydrous) : A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens is replaced by a [(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(isopropyloxycarbonyloxymethyl) ester (disoproxil ester) prodrug is used as the fumaric acid salt in combination therapy for the treatment of HIV infection.	4.9	1	1	nucleoside analogue; phosphonic acids	antiviral drug; drug metabolite; HIV-1 reverse transcriptase inhibitor
shikonin shikonin: a naphthazarin; has antineoplastic and angiogenesis inhibiting activities	2.88	3	0	hydroxy-1,4-naphthoquinone
8-prenylnaringenin 8-prenylnaringenin: a phytogenic antineoplastic agent; structure in first source. sophoraflavanone B : A trihydroxyflavanone that is (S)-naringenin having a prenyl group at position 8.	2.01	1	0	(2S)-flavan-4-one; 4'-hydroxyflavanones; trihydroxyflavanone	plant metabolite; platelet aggregation inhibitor
pallidol pallidol: isolated from Ciccus pallida; structure in first source. pallidol : A tetracyclic stilbenoid that is a homodimer obtained by cyclodimerisation of resveratrol.	2.13	1	0	carbopolycyclic compound; polyphenol; stilbenoid	antifungal agent; antioxidant; plant metabolite
efinaconazole efinaconazole: an antifungal agent; structure in first source. efinaconazole : A member of the class of triazoles that is butan-2-ol which is substituted at positions 1, 2, and 3 by 1,2,4-triazol-1-yl, 2,4-difluorophenyl, and 4-methylenepiperidin-1-yl groups, respectively (the 2R,3R stereoisomer). It is an antifungal drug used for the topical treatment of onychomycosis (a nail infection caused mainly by dermatophytes).	3.21	1	0	conazole antifungal drug; olefinic compound; organofluorine compound; piperidines; tertiary alcohol; tertiary amino compound; triazole antifungal drug	EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor
favipiravir favipiravir : A member of the class of pyrazines that is pyrazine substituted by aminocarbonyl, hydroxy and fluoro groups at positions 2, 3 and 6, respectively. It is an anti-viral agent that inhibits RNA-dependent RNA polymerase of several RNA viruses and is approved for the treatment of influenza in Japan.	4.95	6	0	hydroxypyrazine; organofluorine compound; primary carboxamide	anticoronaviral agent; antiviral drug; EC 2.7.7.48 (RNA-directed RNA polymerase) 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).	2.96	4	0	flavin; vitamin B2	anti-inflammatory agent; antioxidant; cofactor; Escherichia coli metabolite; food colouring; fundamental metabolite; human urinary metabolite; mouse metabolite; photosensitizing agent; plant metabolite
laninamivir laninamivir: an antiviral agent	9.35	30	3	acetamides
evp 4593 EVP 4593: an NF-kappaB pathway inhibitor; structure in first source	2.21	1	0
sodium acetate, anhydrous Sodium Acetate: The trihydrate sodium salt of acetic acid, which is used as a source of sodium ions in solutions for dialysis and as a systemic and urinary alkalizer, diuretic, and expectorant.	2.53	2	0	organic sodium salt	NMR chemical shift reference compound
sodium benzoate Sodium Benzoate: The sodium salt of BENZOIC ACID. It is used as an antifungal preservative in pharmaceutical preparations and foods. It may also be used as a test for liver function.. sodium benzoate : An organic sodium salt resulting from the replacement of the proton from the carboxy group of benzoic acid by a sodium ion.	2.03	1	0	organic sodium salt	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
ammonium acetate ammonium acetate : An ammonium salt obtained by reaction of ammonia with acetic acid. A deliquescent white crystalline solid, it has a relatively low melting point (114degreeC) for a salt. Used as a food acidity regulator, although no longer approved for this purpose in the EU.	2.06	1	0	acetate salt; ammonium salt	buffer; food acidity regulator
oxazolidine oxazolidine: structure given in first source	2.96	4	0	oxazolidine
bromochloroacetic acid Keratins: A class of fibrous proteins or scleroproteins that represents the principal constituent of EPIDERMIS; HAIR; NAILS; horny tissues, and the organic matrix of tooth ENAMEL. Two major conformational groups have been characterized, alpha-keratin, whose peptide backbone forms a coiled-coil alpha helical structure consisting of TYPE I KERATIN and a TYPE II KERATIN, and beta-keratin, whose backbone forms a zigzag or pleated sheet structure. alpha-Keratins have been classified into at least 20 subtypes. In addition multiple isoforms of subtypes have been found which may be due to GENE DUPLICATION.. bromochloroacetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is replaced by bromine while a second is replaced by chlorine. A low-melting (27.5-31.5degreeC), hygroscopic crystalline solid, it can be formed during the disinfection (by chlorination) of water that contains bromide ions and organic matter, so can occur in drinking water as a byproduct of the disinfection process.	1.98	1	0	2-bromocarboxylic acid; monocarboxylic acid; organochlorine compound
3-aminocyclohexanecarboxylic acid 3-aminocyclohexanecarboxylic acid: GABA analog; RN given refers to cis-(+-)-isomer; structure	2.03	1	0
capsaicin [no description available]	2.01	1	0
tris(perfluorophenyl)borane tris(perfluorophenyl)borane: structure in first source	2.13	1	0
tolfenamic acid tolfenamic acid: structure. tolfenamic acid : An aminobenzoic acid that is anthranilic acid in which one of the hydrogens attached to the nitrogen is replaced by a 3-chloro-2-methylphenyl group. Tolfenamic acid is used specifically for relieving the pain of migraine. It also shows anticancer activity.	2.21	1	0	aminobenzoic acid; organochlorine compound; secondary amino compound	EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; EC 2.7.1.33 (pantothenate kinase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
artemisin [no description available]	2.15	1	0
bedt-ttf BEDT-TTF: a deuterated-BEDT-TTF superconductor	2.03	1	0
varitriol varitriol: from marine-derived strain of the fungus Emericella variecolor; structure in first source	2.42	2	0
camalexin camalexin : An indole phytoalexin that is indole substituted at position 3 by a 1,3-thiazol-2-yl group.	6.17	40	0	1,3-thiazoles; indole phytoalexin	metabolite
cinnamaldehyde 3-phenylprop-2-enal : A member of the class of cinnamaldehydes that is prop-2-enal in which a hydrogen at position 3 has been replaced by a phenyl group. The configuration of the double bond is not specified; the name "cinnamaldehyde" is widely used to refer to the E (trans) isomer.. (E)-cinnamaldehyde : The E (trans) stereoisomer of cinnamaldehyde, the parent of the class of cinnamaldehydes.	2.46	2	0	3-phenylprop-2-enal; cinnamaldehydes	antifungal agent; EC 4.3.1.24 (phenylalanine ammonia-lyase) inhibitor; flavouring agent; hypoglycemic agent; plant metabolite; sensitiser; vasodilator agent
trans-4-coumaric acid hydroxycinnamic acid : Any member of the class of cinnamic acids carrying one or more hydroxy substituents.. trans-4-coumaric acid : The trans-isomer of 4-coumaric acid.. 4-coumaric acid : A coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring.	3.18	5	0	4-coumaric acid	food component; mouse metabolite; plant metabolite
anethole anethole: an isomer of estragole; structurally similar to CAPSAICIN; has some neurological and insecticidal and skin absorption effects; RN given refers to unspecified stereoisomer. anethole : A monomethoxybenzene that is methoxybenzene substituted by a prop-1-en-1-yl group at position 4.. trans-anethole : The trans-stereoisomer of anethole.	2.05	1	0	anethole	flavouring agent
geraniol [no description available]	5.82	6	1	3,7-dimethylocta-2,6-dien-1-ol; monoterpenoid; primary alcohol	allergen; fragrance; plant metabolite; volatile oil component
glycosides [no description available]	7.66	51	0
benzylideneacetone benzylideneacetone: RN given refers to cpd without isomeric; structure in Merck Index, 9th ed, #1153. trans-benzylideneacetone : The trans-isomer of benzylideneacetone. It acts as an inhibitor of the enzyme phospholipase A2 (EC 3.1.1.4) of insects like diamond back moth.. benzylideneacetone : An enone in which a phenyl ring is attached to the beta-carbon atom of but-3-en-2-one. Although both cis- and trans-isomers are possible for the alpha,beta-unsaturated ketone, only the trans-isomer is observed.	2	1	0	benzylideneacetone	bacterial metabolite; EC 3.1.1.4 (phospholipase A2) inhibitor; flavouring agent; fragrance
chalcone trans-chalcone : The trans-isomer of chalcone.	3.15	5	0	chalcone	EC 3.2.1.1 (alpha-amylase) inhibitor
sinapinic acid sinapinic acid: a matrix for matrix-assisted laser desorption technique for protein MW determination; a constituent of propolis. trans-sinapic acid : A sinapic acid in which the double bond has trans-configuration.	2.07	1	0	sinapic acid	MALDI matrix material; plant metabolite
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)	6.43	33	0	isomethyleugenol
retinaldehyde Retinaldehyde: A diterpene derived from the carotenoid VITAMIN A which functions as the active component of the visual cycle. It is the prosthetic group of RHODOPSIN (i.e., covalently bonded to ROD OPSIN as 11-cis-retinal). When stimulated by visible light, rhodopsin transforms this cis-isomer of retinal to the trans-isomer (11-trans-retinal). This transformation straightens-out the bend of the retinal molecule and causes a change in the shape of rhodopsin triggering the visual process. A series of energy-requiring enzyme-catalyzed reactions convert the 11-trans-retinal back to the cis-isomer.. all-trans-retinal : A retinal in which all four exocyclic double bonds have E- (trans-) geometry.	3.19	1	0	retinal; vitamin A	gap junctional intercellular communication inhibitor; human metabolite; mouse metabolite
squalene Addavax: an oil-water nanoemulsion and adjuvant containing squalene, Tween 80, and sorbitane trioleate	4.05	13	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.	5.29	47	0	stilbene
diethyl fumarate diethyl fumarate : A dieter obtained by the formal condensation of fumaric acid with ethanol.	2.06	1	0	diester	metabolite
curvularin curvularin: from Penicillium Baradicum Baghdadi; structure	1.95	1	0
3-hexenal 3-hexenal: induced by the Gastrophysa polygoni herbivory on Rumex confertus. 3-hexenal : A hexenal carrying an unsaturation at position 3.	2.83	3	0
flavin-adenine dinucleotide Flavin-Adenine Dinucleotide: A condensation product of riboflavin and adenosine diphosphate. The coenzyme of various aerobic dehydrogenases, e.g., D-amino acid oxidase and L-amino acid oxidase. (Lehninger, Principles of Biochemistry, 1982, p972)	2.9	4	0	flavin adenine dinucleotide; vitamin B2	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; prosthetic group
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.	2.38	2	0	vasopressin	cardiovascular drug; hematologic agent; mitogen
pyrophosphate Diphosphates: Inorganic salts of phosphoric acid that contain two phosphate groups.	3.12	5	0	diphosphate ion
gw9662 2-chloro-5-nitrobenzanilide: pretreatment of peroxisome proliferator activated receptors with GW9662 results in the irreversible loss of ligand binding	2.46	2	0	benzamides
dihydrosphingosine 1-phosphate dihydrosphingosine 1-phosphate: RN given refers to (R-(R,S))-isomer. sphinganine 1-phosphate : A sphingoid 1-phosphate that is the monophosphorylated derivative of sphinganine.	2.11	1	0	sphingoid 1-phosphate	mouse metabolite
glucobrassicin glucobrassicin: isolated from Brussels sprouts; structure given in first source. glucobrassicin : An indolylmethylglucosinolic acid that is 1-thio-beta-D-glucopyranose having a 2-(1H-indol-3-yl)-N-(sulfooxy)ethanimidoyl group attached to the anomeric sulfur.	3.18	5	0	indolyl carbohydrate; indolylmethylglucosinolic acid
4-methoxy-3-indolylmethyl glucosinolate 4-methoxy-3-indolylmethyl glucosinolate: from cabbage, cauliflower & brussels sprouts. 4-methoxyglucobrassicin : An indolylmethylglucosinolic acid that is glucobrassicin bearing a methoxy substituent at position 4 on the indole ring.	2.08	1	0	indolyl carbohydrate; indolylmethylglucosinolic acid
bucillamine [no description available]	2.05	1	0	organic molecular entity
tram 34 TRAM 34: inhibits IKCa1; structure in first source	2.04	1	0	organochlorine compound
isopropyl thiogalactoside Isopropyl Thiogalactoside: A non-metabolizable galactose analog that induces expression of the LAC OPERON.. isopropyl beta-D-thiogalactopyranoside : An S-glycosyl compound consisting of beta-D-1-thiogalactose having an isopropyl group attached to the anomeric sulfur.	2.31	1	0	S-glycosyl compound
nsc 4347 NSC 4347: structure in first source	2.02	1	0
n(6)-cyclopentyladenosine [no description available]	1.98	1	0
sesquiterpenes [no description available]	8.93	148	0
mercaptopurine Mercaptopurine: An antimetabolite antineoplastic agent with immunosuppressant properties. It interferes with nucleic acid synthesis by inhibiting purine metabolism and is used, usually in combination with other drugs, in the treatment of or in remission maintenance programs for leukemia.. purine-6-thiol : A thiol that is the tautomer of mercaptopurine.. mercaptopurine : A member of the class of purines that is 6,7-dihydro-1H-purine carrying a thione group at position 6. An adenine analogue, it is used in the treatment of acute lymphocytic leukemia (ALL), chronic myeloid leukemia (CML), Crohn's disease, and ulcerative colitis.	2.86	4	0	aryl thiol; purines; thiocarbonyl compound	anticoronaviral agent; antimetabolite; antineoplastic agent
vasicine vasicine: RN given refers to (R)-isomer	2.15	1	0
3,3',4,5'-tetrahydroxystilbene 3,3',4,5'-tetrahydroxystilbene: demethyl derivative of isorhapontigenin; structure in first source; a Syk kinase inhibitor; found in heartwood of FABACEAE; inhibitor of photosynthesis in spinach chloroplasts; may be inhibitor of plant growth; RN given refers to (E)-isomer. piceatannol : A stilbenol that is trans-stilbene in which one of the phenyl groups is substituted by hydroxy groups at positions 3 and 4, while the other phenyl group is substituted by hydroxy groups at positions 3 and 5.	2.8	3	0	catechols; polyphenol; resorcinols; stilbenol	antineoplastic agent; apoptosis inducer; geroprotector; hypoglycemic agent; plant metabolite; protein kinase inhibitor; tyrosine kinase inhibitor
thioinosine Thioinosine: Sulfhydryl analog of INOSINE that inhibits nucleoside transport across erythrocyte plasma membranes, and has immunosuppressive properties. It has been used similarly to MERCAPTOPURINE in the treatment of leukemia. (From Martindale, The Extra Pharmacopoeia, 30th ed, p503)	2.42	2	0
phenylthiourea Phenylthiourea: Phenylthiourea is a THIOUREA derivative containing a phenyl ring. Depending on their genetic makeup, humans can find it either bitter-tasting or tasteless.. N-phenylthiourea : A member of the class of thioureas that is thiourea in which one of the hydrogens is replaced by a phenyl group. Depending on their genetic makeup, humans find it either very bitter-tasting or tasteless. This unusual property resulted in N-phenylthiourea being used in paternity testing prior to the advent of DNA testing.	1.98	1	0	thioureas	EC 1.14.18.1 (tyrosinase) inhibitor
caffeic acid trans-caffeic acid : The trans-isomer of caffeic acid.	3.44	7	0	caffeic acid	geroprotector; mouse metabolite
1,6-anhydro-3,4-dideoxy-beta-d-glycero-hex-3-enopyran-2-ulose 1,6-anhydro-3,4-dideoxyhex-3-enopyran-2-ulose: structure in first source	2.44	2	0	anhydrohexose; deoxyketohexose
pyrantel Pyrantel: A depolarizing neuromuscular-blocking agent, that causes persistent nicotinic activation resulting in spastic paralysis of susceptible nematodes. It is a drug of second-choice after benzimidazoles for treatment of ascariasis, hookworm, and pinworm infections, being effective after a single dose. (From Smith and Reynard, Textbook of Pharmacology, 1992, p920). pyrantel : A carboxamidine that is 1,4,5,6-tetrahydropyrimidine that is substituted at position 1 by a methyl group and at position 2 by an (E)-2-(2-thienyl)vinyl group. It is used, particularly as the embonate [4,4'-methylenebis(3-hydroxy-2-naphthoate)] salt, as an anthelmintic that is effective against intestinal nematodes including threadworms, roundworms and hookworms, and is included in the WHO 'Model List of Essential Medicines'.	1.95	1	0	1,4,5,6-tetrahydropyrimidines; carboxamidine; thiophenes	antinematodal drug
loline loline: RN given from CAS Index Guide (1982-1986), p.1019G. loline : A loline alkaloid with formula C8H14N2O.	2.04	1	0	loline alkaloid; secondary amino compound
3-amino-n-(4-methoxybenzyl)-4,6-dimethylthieno(2,3-b)pyridine-2-carboxamide 3-amino-N-(4-methoxybenzyl)-4,6-dimethylthieno(2,3-b)pyridine-2-carboxamide: structure in first source	2.21	1	0
dieldrin Dieldrin: An organochlorine insecticide whose use has been cancelled or suspended in the United States. It has been used to control locusts, tropical disease vectors, in termite control by direct soil injection, and non-food seed and plant treatment. (From HSDB). dieldrin : An organochlorine compound resulting from the epoxidation of the double bond of aldrin. It is the active metabolite of the proinsecticde aldrin.	2.03	1	0	epoxide; organochlorine compound; organochlorine insecticide	carcinogenic agent; xenobiotic
curcumin Curcumin: A yellow-orange dye obtained from tumeric, the powdered root of CURCUMA longa. It is used in the preparation of curcuma paper and the detection of boron. Curcumin appears to possess a spectrum of pharmacological properties, due primarily to its inhibitory effects on metabolic enzymes.. curcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa.	6.37	11	1	aromatic ether; beta-diketone; diarylheptanoid; enone; polyphenol	anti-inflammatory agent; antifungal agent; antineoplastic agent; biological pigment; contraceptive drug; dye; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; EC 1.8.1.9 (thioredoxin reductase) inhibitor; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; flavouring agent; food colouring; geroprotector; hepatoprotective agent; immunomodulator; iron chelator; ligand; lipoxygenase inhibitor; metabolite; neuroprotective agent; nutraceutical; radical scavenger
benztropine Benztropine: A centrally active muscarinic antagonist that has been used in the symptomatic treatment of PARKINSON DISEASE. Benztropine also inhibits the uptake of dopamine.. benzatropine : Tropane in which a hydrogen at position 3 is substituted by a diphenylmethoxy group (endo-isomer). An acetylcholine receptor antagonist, it is used (particularly as its methanesulphonate salt) in the treatment of Parkinson's disease, and to reduce parkinsonism and akathisia side effects of antipsychotic treatments.	1.96	1	0	diarylmethane
trithiocyanuric acid trithiocyanuric acid: rubber curative; RN given refers to parent cpd	2.07	1	0
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).	2.11	1	0	carbobicyclic compound; enone; sesquiterpenoid	fragrance; insect repellent; plant metabolite
thiohydantoins Thiohydantoins: Sulfur analogs of hydantoins with one or both carbonyl groups replaced by thiocarbonyl groups.	2.6	1	0
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.	5.42	7	2	capsaicinoid	non-narcotic analgesic; TRPV1 agonist; voltage-gated sodium channel blocker
terbinafine [no description available]	2.51	2	0	acetylenic compound; allylamine antifungal drug; enyne; naphthalenes; tertiary amine	EC 1.14.13.132 (squalene monooxygenase) inhibitor; P450 inhibitor; sterol biosynthesis inhibitor
Jasmone jasmone: RN refers to (Z)-isomer; structure given in first source	7.56	53	0	cyclic ketone
geranyl acetate geranyl acetate: constituted about 90% of the palmarosa oil. geranyl acetate : A monoterpenoid that is the acetate ester derivative of geraniol.	2.17	1	0	acetate ester; monoterpenoid	plant metabolite
coniferyl alcohol coniferyl alcohol: structure. coniferol : A phenylpropanoid that is one of the main monolignols, produced by the reduction of the carboxy functional group in cinnamic acid and the addition of a hydroxy and a methoxy substituent to the aromatic ring.	2.03	1	0	guaiacols; phenylpropanoid	animal metabolite; monolignol; mouse metabolite; pheromone; plant metabolite; volatile oil component
citralva citralva: citrus odourant	1.99	1	0
chlorogenic acid caffeoylquinic acid: Antiviral Agent; structure in first source. chlorogenate : A monocarboxylic acid anion that is the conjugate base of chlorogenic acid; major species at pH 7.3.	3.31	6	0	cinnamate ester; tannin	food component; plant metabolite
CAY10591 CAY10591: a SIRT1 NAD-dependent histone deacetylase activator	2.66	2	0	quinoxaline derivative
cct007093 [no description available]	2.77	3	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.	1.94	1	0	2-aminopurines	anticoronaviral agent; antimetabolite; antineoplastic agent
1,3-dimethylthiourea [no description available]	2.79	3	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.	3.2	5	0	one-carbon compound; thioureas; ureas	antioxidant; chromophore
indigo carmine Indigo Carmine: Indolesulfonic acid used as a dye in renal function testing for the detection of nitrates and chlorates, and in the testing of milk.. indigo carmine : An organic sodium salt resulting from the formal condensation of indigo carmine (acid form) with two equivalents of sodium hydroxide. It is an indicator at pH 11.5-14, changing from blue to yellow.	2.21	1	0
D-fructopyranose [no description available]	3.91	12	0	cyclic hemiketal; D-fructose; fructopyranose	sweetening agent
tempo TEMPO: structure. TEMPO : A member of the class of aminoxyls that is piperidine that carries an oxidanediyl group at position 1 and methyl groups at positions 2, 2, 6, and 6, respectively.	2.93	4	0	aminoxyls; piperidines	catalyst; ferroptosis inhibitor; radical scavenger
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.	1.95	1	0	cardenolide glycoside; steroid saponin	anti-arrhythmia drug; cardiotonic drug; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; epitope
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.	3.14	5	0	diester; fumonisin; primary amino compound; triol	carcinogenic agent; metabolite
1,3-dihydroxy-4,4,5,5-tetramethyl-2-(4-carboxyphenyl)tetrahydroimidazole 1,3-dihydroxy-4,4,5,5-tetramethyl-2-(4-carboxyphenyl)tetrahydroimidazole: intermediate in the synthesis of imidazolineoxyl N-oxides; partial structure given in first source	2.98	4	0	benzoic acid; imidazolines; organic radical	apoptosis inhibitor; radical scavenger
2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide: partial structure given in first source; endothelium-derived relaxing factor antagonist	2.02	1	0
tamoxifen [no description available]	3.79	10	0	stilbenoid; tertiary amino compound	angiogenesis inhibitor; antineoplastic agent; bone density conservation agent; EC 1.2.3.1 (aldehyde oxidase) inhibitor; EC 2.7.11.13 (protein kinase C) inhibitor; estrogen antagonist; estrogen receptor antagonist; estrogen receptor modulator
nadp [no description available]	7.2	17	1
1,1-diphenyl-2-picrylhydrazyl 1,1-diphenyl-2-picrylhydrazyl: A diphenyl picrate; the ability to decolorize this stable radical indicates reactivity of tested compounds (Banda, Anal Chem 46:1772-7 1974)	3.56	8	0
3-cyclopentyloxy-4-methoxybenzaldehyde 3-cyclopentyloxy-4-methoxybenzaldehyde: structure in first source	2.02	1	0
mercuric triflate mercuric triflate: structure in first source	2.05	1	0
t 0070907 T 0070907: a PPARgamma antagonist; structure in first source	2.05	1	0	carbonyl compound; organohalogen compound
sirtinol [no description available]	2.11	1	0	aldimine; benzamides; naphthols	anti-inflammatory agent; EC 3.5.1.98 (histone deacetylase) inhibitor; Sir2 inhibitor
apcin apcin: inhibits the anaphase-promoting complex; structure in first source	2.15	1	0
artemotil artemotil: structure given in first source; RN given refers to cpd without isomeric designation	2.11	1	0	artemisinin derivative
thiopental Thiopental: A barbiturate that is administered intravenously for the induction of general anesthesia or for the production of complete anesthesia of short duration.. thiopental : A barbiturate, the structure of which is that of 2-thiobarbituric acid substituted at C-5 by ethyl and sec-pentyl groups.	1.94	1	0	barbiturates	anticonvulsant; drug allergen; environmental contaminant; intravenous anaesthetic; sedative; xenobiotic
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.	1.99	1	0	C-nitro compound; furans; organic sulfide; tertiary amino compound	anti-ulcer drug; drug allergen; environmental contaminant; H2-receptor antagonist; xenobiotic
nnd 502 luliconazole: structure in first source	3.21	1	0	dichlorobenzene
u 0126 U 0126: protein kinase kinase inhibitor; structure in first source	3.01	4	0	aryl sulfide; dinitrile; enamine; substituted aniline	antineoplastic agent; antioxidant; apoptosis inducer; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; osteogenesis regulator; vasoconstrictor agent
laccase Laccase: A copper-containing oxidoreductase enzyme that catalyzes the oxidation of 4-benzenediol to 4-benzosemiquinone. It also has activity towards a variety of O-quinols and P-quinols. It primarily found in FUNGI and is involved in LIGNIN degradation, pigment biosynthesis and detoxification of lignin-derived products.	2.17	1	0
6-methyl-2-(phenylethynyl)pyridine 6-methyl-2-(phenylethynyl)pyridine: an mGlu5 antagonist. 2-methyl-6-(phenylethynyl)pyridine : A methylpyridine that coinsists of 2-methylp[yridine bearing an additional phenylethynyl group at position 6. Potent and highly selective non-competitive antagonist at the mGlu5 receptor subtype (IC50 = 36 nM) and a positive allosteric modulator at mGlu4 receptors. Centrally active following systemic administration in vivo. Reverses mechanical hyperalgesia in the inflamed rat hind paw.	2.97	4	0	acetylenic compound; methylpyridines	anxiolytic drug; metabotropic glutamate receptor antagonist
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.	9.5	23	0	alkali metal atom
nitrogen dioxide Nitrogen Dioxide: Nitrogen oxide (NO2). A highly poisonous gas. Exposure produces inflammation of lungs that may only cause slight pain or pass unnoticed, but resulting edema several days later may cause death. (From Merck, 11th ed) It is a major atmospheric pollutant that is able to absorb UV light that does not reach the earth's surface.	2.17	1	0	nitrogen oxide
mitragynine [no description available]	2.07	1	0	monoterpenoid indole alkaloid
((5,6-dichloro-2,3,9,9a-tetrahydro-3-oxo-9a-propyl-1h-fluoren-7-yl)oxy)acetic acid L 644711: RN given refers to (R)-isomer; structure given in first source; HCO3(-)/Cl(-) antiporter antagonist	2.04	1	0
2,2-dimethyl-5-hydroxy-1-pyrrolidinyloxy 2,2-dimethyl-5-hydroxy-1-pyrrolidinyloxy: structure given in first source	1.99	1	0
rtki cpd RTKI cpd: preferentially inhibits human glioma cells expressing truncated rather than wild-type epidermal growth factor receptors	2.17	1	0
5-methoxypodophyllotoxin 5-methoxypodophyllotoxin: from root culture of Linum flavum; structure given in first source	2.02	1	0	furonaphthodioxole
n,n'-methylene-bis(2-amino-5-sulfhydryl-1,3,4-thiadiazole) bismerthiazol: a bactericide and fungicide	2.13	1	0
cystine [no description available]	6.09	5	1
u-50488 3,4-Dichloro-N-methyl-N-(2-(1-pyrrolidinyl)-cyclohexyl)-benzeneacetamide, (trans)-Isomer: A non-peptide, kappa-opioid receptor agonist which has also been found to stimulate the release of adrenocorticotropin (ADRENOCORTICOTROPIC HORMONE) via the release of hypothalamic arginine vasopressin (ARGININE VASOPRESSIN) and CORTICOTROPIN-RELEASING HORMONE. (From J Pharmacol Exp Ther 1997;280(1):416-21). U50488 : A monocarboxylic acid amide obtained by formal condensation between the carboxy group of 3,4-dichlorophenylacetic acid and the secondary amino group of (1R,2R)-N-methyl-2-(pyrrolidin-1-yl)cyclohexanamine	3.08	1	0	dichlorobenzene; monocarboxylic acid amide; N-alkylpyrrolidine	analgesic; antitussive; calcium channel blocker; diuretic; kappa-opioid receptor agonist
c,n-diphenylnitrone C,N-diphenylnitrone: structure in first source	2.03	1	0
ro 31-6930 Ro 31-6930: potassium channel opener	1.98	1	0
isobutyryl-coenzyme a [no description available]	2.17	1	0	methyl-branched fatty acyl-CoA; short-chain fatty acyl-CoA	human metabolite; mouse metabolite
safingol safingol: RN given refers to the (R-(R,S))-isomer	2.43	2	0	amino alcohol
2-oxindole-3-acetic acid 2-oxindole-3-acetic acid: personal communication from searcher Ellen V. Todd Alabama Center 1/72. 2-oxindole-3-acetic acid : A member of the class of oxindoles that is 2-oxindole carrying a carboxymethyl substituent at position 3.	2.11	1	0	indole-3-acetic acids; monocarboxylic acid; oxindoles	plant metabolite
oxalylglycine oxalylglycine: structure given in first source. N-oxalylglycine : An amino dicarboxylic acid that is iminodiacetic acid with an oxo substituent. It is used as an inhibitor of alpha-ketoglutarate dependent (EC 1.14.11.*) enzymes.	2.13	1	0	amino dicarboxylic acid; N-acylglycine	EC 1.14.11.* (oxidoreductase acting on paired donors, 2-oxoglutarate as one donor, incorporating 1 atom each of oxygen into both donors) inhibitor
pelargonidin-3-glucoside pelargonidin-3-glucoside: structure given in first source; RN given for chloride salt; RN for parent cpd not available 1/93. pelargonidin 3-O-beta-D-glucoside chloride : A member of the class of anthocyanin chlorides that has pelargonidin 3-O-beta-D-glucoside as the cationic counterpart.	2.13	1	0	anthocyanin chlorides
ascorbigen ascorbigen: a depot form of ascorbic acid. ascorbigen : An indolyl carbohydrate that consists of (3aS,6S,6aR)-3,3a,6-trihydroxy-3-tetrahydrofuro[3,2-b]furan-2-one in which position 3 is substituted by an indol-3-ylmethyl group. Formed from indole-3-carbinol and ascorbic acid in brassica vegetables.	2	1	0	indolyl carbohydrate	metabolite
ferrocenium ferrocenium: structure given in first source	2.01	1	0
calixarenes Calixarenes: Phenolic metacyclophanes derived from condensation of PHENOLS and ALDEHYDES. The name derives from the vase-like molecular structures. A bracketed [n] indicates the number of aromatic rings.. calixarenes : Originally macrocyclic compounds capable of assuming a basket (or "calix") shaped conformation. They are formed from p-hydrocarbyl phenols and formaldehyde. The term now applies to a variety of derivatives by substitution of the hydrocarbon cyclo{oligo[(1,3-phenylene)methylene]}.. calixarene : A macrocycle composed of 1,3-phenylene groups linked by methylene groups. The number of 1,3-phenylene units in the macrocycle is denoted by the "n" in calix[n]arene name.	2.04	1	0
phosphoribosylamine [no description available]	1.97	1	0	ribose monophosphate; ribosylamine
18-crown-6 2,3,11,12-tetracarboxylic acid 18-crown-6 2,3,11,12-tetracarboxylic acid: structure in first source; RN given for (2R,3R,11,12)-isomer	2.05	1	0
phyd protein, arabidopsis PHYD protein, Arabidopsis: belongs to the phytochrome apoprotein family in Arabidopsis; GenBank X76609	2.07	1	0
amanitins Amanitins: Cyclic peptides extracted from carpophores of various mushroom species. They are potent inhibitors of RNA polymerases in most eukaryotic species, blocking the production of mRNA and protein synthesis. These peptides are important in the study of transcription. Alpha-amanitin is the main toxin from the species Amanitia phalloides, poisonous if ingested by humans or animals.	1.98	1	0
cytellin cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982	2.44	2	0
momilactone b momilactone B: structure in first source	3.56	2	0	organic heterotricyclic compound; organooxygen compound
ginsenosides ginsenoside : Triterpenoid saponins with a dammarane-like skeleton originally isolated from ginseng (Panax) species. Use of the term has been extended to include semi-synthetic derivatives.	6.39	29	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.	1.98	1	0	adenosines; dicarboxylic acid monoamide; monocarboxylic acid	adenosine A2A receptor agonist; anti-inflammatory agent
2,3-dioxo-6-nitro-7-sulfamoylbenzo(f)quinoxaline 2,3-dioxo-6-nitro-7-sulfamoylbenzo(f)quinoxaline: structure given in first source; neuroprotectant for cerebral ischemia; AMPA receptor antagonist	2.44	2	0	naphthalenes; sulfonic acid derivative
ovalbumin Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.	3.85	12	0
3,4-dicarboxyphenylglycine 3,4-dicarboxyphenylglycine: structure in first source	2.02	1	0
epoxiconazole epoxiconazole : A racemate composed of equimolar amounts of (2S,3R)- and (2R,3S)-epoxiconazole. A broad-spectrum fungicide for control of diseases caused by Ascomycetes, Basidiomycetes and Deuteromycetes. Epoxiconazole is moderately toxic to birds, honeybees, earthworms and most aquatic organisms.. 1-{[3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole : An epoxide that is oxirane substituted by a 2-chlorophenyl, 4-fluorophenyl and a 1H-1,2,4-triazol-1-ylmethyl groups.	2.21	1	0	epoxide; monochlorobenzenes; monofluorobenzenes; triazoles
sodium dodecyl sulfate Sodium Dodecyl Sulfate: An anionic surfactant, usually a mixture of sodium alkyl sulfates, mainly the lauryl; lowers surface tension of aqueous solutions; used as fat emulsifier, wetting agent, detergent in cosmetics, pharmaceuticals and toothpastes; also as research tool in protein biochemistry.. sodium dodecyl sulfate : An organic sodium salt that is the sodium salt of dodecyl hydrogen sulfate.	2.68	3	0	organic sodium salt	detergent; protein denaturant
ncs 382 NCS 382: structure given in first source	2.08	1	0
n-isobutyl-decanamide N-isobutyl-decanamide: structure in first source	2.05	1	0
mtt formazan MTT formazan: a blue MEM-insoluble mitochondrial byproduct; used to determine viability of cells with active mitochondrial dehydrogenase enzymes	2.01	1	0
flavan-3-ol flavan-3-ol: structure in first source	2.59	2	0	hydroxyflavonoid
6-cyano-7-nitroquinoxaline-2,3-dione 6-Cyano-7-nitroquinoxaline-2,3-dione: A potent excitatory amino acid antagonist with a preference for non-NMDA iontropic receptors. It is used primarily as a research tool.	3.25	6	0	quinoxaline derivative
zinc protoporphyrin ix [no description available]	2.08	1	0
fg 9041 FG 9041: structure given in first source	2.39	2	0	quinoxaline derivative
4-nitrocaramiphen [no description available]	1.98	1	0	C-nitro compound
homoserine lactone homoserine lactone: a putative signal for starvation in E. coli; structure in first source. homoserinium lactone : The conjugate acid of homoserine lactone; major species at pH 7.3.. homoserine lactone : A butan-4-olide having an amino substituent at the 2-position.	2.03	1	0	ammonium ion derivative; organic cation
alpha-chymotrypsin Chymotrypsin: A serine endopeptidase secreted by the pancreas as its zymogen, CHYMOTRYPSINOGEN and carried in the pancreatic juice to the duodenum where it is activated by TRYPSIN. It selectively cleaves aromatic amino acids on the carboxyl side.	2.67	3	0
17-ketosteroids 17-Ketosteroids: Steroids that contain a ketone group at position 17.. 17-oxo steroid : Any oxo steroid carrying the oxo group at position 17.	3.45	2	0
naphthoquinones Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.	4.11	14	0
sodium borohydride sodium borohydride: RN given refers to parent cpd	2.46	2	0	inorganic sodium salt; metal tetrahydridoborate
(r,s)-5,7-di-tert-butyl-3-hydroxy-3-trifluoromethyl-3h-benzofuran-2-one (R,S)-5,7-di-tert-butyl-3-hydroxy-3-trifluoromethyl-3H-benzofuran-2-one: a positive allosteric modulator of GABAB receptors; structure in first source	2.81	3	0
cfm 2 CFM 2: structure in first source	2.01	1	0	benzodiazepine
cathepsin g Cathepsin G: A serine protease found in the azurophil granules of NEUTROPHILS. It has an enzyme specificity similar to that of chymotrypsin C.	2.68	3	0
3-(2-hydroxy-4-(1,1-dimethylheptyl)phenyl)-4-(3-hydroxypropyl)cyclohexanol 3-(2-hydroxy-4-(1,1-dimethylheptyl)phenyl)-4-(3-hydroxypropyl)cyclohexanol: (-)-CP-55,940 and (+)-CP-56,667 are enantiomers; RN refers to CP-55,940	2.07	1	0	alkylbenzene; ring assembly
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.	2.43	2	0	organic cation; xanthene dye	fluorochrome
4-hydroxy-5-methyl-3(2h)-furanone 4-hydroxy-5-methyl-3-furanone : A member of the class of furans that is 5-methyl-2,3-dihydrofuran with a hydroxy group at position 4 and a keto group at position 3.	2.01	1	0	cyclic ketone; enol; furans	metabolite
myelin basic protein Myelin Basic Protein: An abundant cytosolic protein that plays a critical role in the structure of multilamellar myelin. Myelin basic protein binds to the cytosolic sides of myelin cell membranes and causes a tight adhesion between opposing cell membranes.	2.89	4	0
cgp 7930 2,6-di-tert-butyl-4-(3-hydroxy-2,2-dimethylpropyl)phenol: structure in first source	2.94	4	0	alkylbenzene
methanethiosulfonate methanethiosulfonate: used for measurement of rhodanese activity; RN given refers to parent cpd	1.94	1	0
dimethyl maleate dimethyl maleate: structure. dimethyl maleate : A maleate ester resulting from the formal condensation of both carboxy groups of maleic acid with methanol. It is commonly used as a dienophile for Diels-Alder-type cycloaddition reactions in organic synthesis.	2.03	1	0	diester; maleate ester; methyl ester
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.	1.99	1	0	ethyl ester; maleate ester	glutathione depleting agent
leachianone g leachianone G: structure in first source. leachianone G : A tetrahydroxyflavanone having the hydroxy groups at the 2'-, 4'-, 5- and 7-positions and a prenyl group at 8-position.	2.01	1	0	(2S)-flavan-4-one; 4'-hydroxyflavanones; tetrahydroxyflavanone
farnesoic acid farnesoic acid : A methyl-branched, trienoic fatty acid consisting of dodeca-2,6,10-trienoic acid having three methyl substituents at the 3-, 7- and 11-positions.. (2E,6E)-farnesoic acid : A farnesoic acid in which the double bonds at positions 2 and 6 both have E-configuration.	2.01	1	0	farnesoic acid	animal metabolite
grl 02031 GRL 02031: a protease inhibitor with anti-HIV1 activity; structure in first source	2.05	1	0
ku 55933 2-morpholin-4-yl-6-thianthren-1-yl-pyran-4-one: specific inhibitor of the ataxia-telangiectasia mutated kinase ATM; structure in first source	2.25	1	0
sphingosine sphing-4-enine : A sphingenine in which the C=C double bond is located at the 4-position.. sphingenine : A 2-aminooctadecene-1,3-diol having (2S,3R)-configuration.. sphingoid : Sphinganine, its homologs and stereoisomers, and the hydroxy and unsaturated derivatives of these compounds.. 2-aminooctadec-4-ene-1,3-diol : A 2-aminooctadecene-1,3-diol having its double bond at position 4.	4.06	14	0	sphing-4-enine	human metabolite; mouse metabolite
quercetin [no description available]	4.31	18	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]	2.01	1	0	biladienes; dicarboxylic acid	antioxidant; human metabolite; mouse metabolite
dinoprostone prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.	6.82	19	1	prostaglandins E	human metabolite; mouse metabolite; oxytocic
dinoprost Dinoprost: A naturally occurring prostaglandin that has oxytocic, luteolytic, and abortifacient activities. Due to its vasocontractile properties, the compound has a variety of other biological actions.. prostaglandin F2alpha : A prostaglandins Falpha that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15. It is a naturally occurring prostaglandin used to induce labor.	2.7	3	0	monocarboxylic acid; prostaglandins Falpha	human metabolite; mouse metabolite
formononetin [no description available]	2.53	2	0	4'-methoxyisoflavones; 7-hydroxyisoflavones	phytoestrogen; plant metabolite
sinapine sinapine: black mustard seeds, seeds of Brassica nigra; RN given refers to parent; structure. sinapine : An acylcholine in which the acyl group specified is sinapoyl.	2.02	1	0	acylcholine	antioxidant; photosynthetic electron-transport chain inhibitor; plant metabolite
sterigmatocystin [no description available]	2.44	2	0	sterigmatocystins	metabolite
fumarylacetoacetate fumarylacetoacetate: metabolite of tyrosine; RN given for (E)-isomer; structure in first source	2.25	1	0	beta-diketone; dicarboxylic fatty acid; oxo dicarboxylic acid
12-oxophytodienoic acid 12-oxophytodienoic acid: structure given in first source; a jasmonate precursor that induces phytoalexin synthesis	9.07	130	0	carbocyclic fatty acid; olefinic fatty acid; oxo carboxylic acid
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.	3.22	5	0	trihydroxyflavone	antineoplastic agent; metabolite
luteolin [no description available]	2.74	3	0	3'-hydroxyflavonoid; tetrahydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; apoptosis inducer; c-Jun N-terminal kinase inhibitor; EC 2.3.1.85 (fatty acid synthase) inhibitor; immunomodulator; nephroprotective agent; plant metabolite; radical scavenger; vascular endothelial growth factor receptor antagonist
7,3'-dihydroxy-4'-methoxyisoflavone 7,3'-dihydroxy-4'-methoxyisoflavone: isolated from Astragali radix; structure in first source. calycosin : A member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone which is substituted by an additional hydroxy group at the 3' position and a methoxy group at the 4' position.	2.11	1	0	4'-methoxyisoflavones; 7-hydroxyisoflavones	antioxidant; 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.	6.07	21	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
scopoletin [no description available]	3.29	6	0	hydroxycoumarin	plant growth regulator; plant metabolite
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.	3.02	4	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.	2.9	4	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.	2.06	1	0	dihydroxy monocarboxylic acid; hydroxy polyunsaturated fatty acid; leukotriene; long-chain fatty acid	human metabolite; mouse metabolite; plant metabolite; vasoconstrictor agent
thromboxane a2 Thromboxane A2: An unstable intermediate between the prostaglandin endoperoxides and thromboxane B2. The compound has a bicyclic oxaneoxetane structure. It is a potent inducer of platelet aggregation and causes vasoconstriction. It is the principal component of rabbit aorta contracting substance (RCS).. thromboxane A2 : A thromboxane which is produced by activated platelets and has prothrombotic properties: it stimulates activation of new platelets as well as increases platelet aggregation.	3.05	1	0	epoxy monocarboxylic acid; thromboxanes A	mouse metabolite
coniferaldehyde coniferaldehyde: from aqueous extract of Senra incana. coniferyl aldehyde : A member of the class of cinnamaldehydes that is cinnamaldehyde substituted by a hydroxy group at position 4 and a methoxy group at position 3.	2.46	2	0	cinnamaldehydes; guaiacols; phenylpropanoid	antifungal agent; plant metabolite
feruloyltyramine feruloyltyramine: structure given in first source; isolated from Cannabis sativa seeds, roots, leaves, and resin; induces hypothermia and motor incoordination in mice; moupinamide is (E)-isomer	2.25	1	0	tyramines	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.	1.98	1	0	hydroxycoumarin	antineoplastic agent; hyaluronic acid synthesis inhibitor
15-ketoprostaglandin e2 15-ketoprostaglandin E2: metabolite of PGE2; RN given refers to (5Z,11alpha,13E)-isomer	2.03	1	0	prostaglandins E
alprostadil [no description available]	2.69	3	0	prostaglandins E	anticoagulant; human metabolite; platelet aggregation inhibitor; vasodilator agent
vitamin d 2 Ergocalciferols: Derivatives of ERGOSTEROL formed by ULTRAVIOLET RAYS breaking of the C9-C10 bond. They differ from CHOLECALCIFEROL in having a double bond between C22 and C23 and a methyl group at C24.. vitamin D2 : A vitamin D supplement and has been isolated from alfalfa.	2.04	1	0	hydroxy seco-steroid; seco-ergostane; vitamin D	bone density conservation agent; nutraceutical; plant metabolite; rodenticide
cholecalciferol Cholecalciferol: Derivative of 7-dehydroxycholesterol formed by ULTRAVIOLET RAYS breaking of the C9-C10 bond. It differs from ERGOCALCIFEROL in having a single bond between C22 and C23 and lacking a methyl group at C24.. calciol : A hydroxy seco-steroid that is (5Z,7E)-9,10-secocholesta-5,7,10(19)-triene in which the pro-S hydrogen at position 3 has been replaced by a hydroxy group. It is the inactive form of vitamin D3, being hydroxylated in the liver to calcidiol (25-hydroxyvitamin D3), which is then further hydroxylated in the kidney to give calcitriol (1,25-dihydroxyvitamin D3), the active hormone.	3.63	3	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.	6.45	12	1	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite
kaempferol [no description available]	3.85	11	0	7-hydroxyflavonol; flavonols; tetrahydroxyflavone	antibacterial agent; geroprotector; human blood serum metabolite; human urinary metabolite; human xenobiotic metabolite; plant metabolite
prostaglandin a2 prostaglandin A2: RN given refers to (5Z,13E,15S)-isomer	3.62	9	0	prostaglandins A	human metabolite
9-deoxy-delta-9-prostaglandin d2 9-deoxy-delta-9-prostaglandin D2: has potent antineoplastic & weak smooth muscle contracting activities; structure given in first source. prostaglandin J2 : A member of the class of prostaglandins J that consists of prosta-5,9,13-trien-1-oic acid substituted by an oxo group at position 11 and a hydroxy group at position 15 (the 5Z,13E,15S stereoisomer).	4.72	9	0	prostaglandins J	human metabolite
6-ketoprostaglandin f1 alpha 6-Ketoprostaglandin F1 alpha: The physiologically active and stable hydrolysis product of EPOPROSTENOL. Found in nearly all mammalian tissue.. 6-oxoprostaglandin F1alpha : A prostaglandin Falpha that is prostaglandin F1alpha bearing a keto substituent at the 6-position.	1.99	1	0	prostaglandins Falpha	human metabolite; mouse 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.	7.82	57	0	linolenic acid; omega-3 fatty acid	micronutrient; mouse metabolite; nutraceutical
naringenin chalcone naringenin chalcone: RN given refers to cpd with unspecified stereoisomer & from CA Vol 92 Form Index; RN for cpd not in Chemline 7/6/83; structure in first source. 2',4,4',6'-tetrahydroxychalcone : A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 2' ,4, 4', and 6' respectively.	2.11	1	0	chalcones; polyphenol	anti-allergic agent; anti-inflammatory agent; metabolite
genistein [no description available]	3.14	5	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.	2.37	2	0	antibiotic antifungal drug; macrolide antibiotic; polyene antibiotic	antiamoebic agent; antiprotozoal drug; bacterial metabolite
carboprost Carboprost: A nonsteroidal abortifacient agent that is effective in both the first and second trimesters of PREGNANCY.. carboprost : Prostaglandin F2alpha in which the hydrogen at position 15 is substituted by methyl (S configuration). It is used as an abortifacient agent that is effective in both the first and second trimesters of pregnancy.	1.96	1	0	hydroxy monocarboxylic acid	abortifacient; oxytocic
tentoxin tentoxin: cyclic peptide from fungus Alternaria tenuis Auct.; structure	3.16	1	0	lactam
jasmonic acid jasmonic acid: a derivative of alpha-linolenic acid that has a role in plant response to herbivory analogous to the role of prostanoids in inflammation in mammals;. jasmonic acid : An oxo monocarboxylic acid that is (3-oxocyclopentyl)acetic acid substituted by a (2Z)-pent-2-en-1-yl group at position 2 of the cyclopentane ring.	18.25	3,627	1	oxo monocarboxylic acid	jasmonates; plant metabolite
2-hexenal, z-isomer 2-hexenal: product of lipid peroxidation in the rat liver; a green odor chemical; do not confuse with the hexabarbital synonym, hexenal; RN given refers to cpd without isomeric designation. 2-hexenal : A hexenal having the double bond at the 2-position.. (2E)-hexenal : A 2-hexenal in which the olefinic double bond has E configuration. It occurs naturally in a wide range of fruits, vegetables, and spices.	3.68	9	0	2-hexenal	antibacterial agent; flavouring agent; plant metabolite
astaxanthine astaxanthine: a keto form of carotene; pigment in flesh of Scottish salmon (Salmo salar) crustacoa-lobster (Homarus gammarus, flamingo feathers; structure; a carotenoid without vitamin A activity, has shown anti-oxidant and anti-inflammatory activities. astaxanthin : A carotenone that consists of beta,beta-carotene-4,4'-dione bearing two hydroxy substituents at positions 3 and 3' (the 3S,3'S diastereomer). A carotenoid pigment found mainly in animals (crustaceans, echinoderms) but also occurring in plants. It can occur free (as a red pigment), as an ester, or as a blue, brown or green chromoprotein.	3.2	5	0	carotenol; carotenone	animal metabolite; anticoagulant; antioxidant; food colouring; plant metabolite
fucoxanthin fucoxanthin: RN given refers to (3S,3'S,5R,5'R,6S,6'R)-isomer. fucoxanthin : An epoxycarotenol that is found in brown seaweed and which exhibits anti-cancer, anti-diabetic, anti-oxidative and neuroprotective properties.	2.13	1	0
lutein Lutein: A xanthophyll found in the major LIGHT-HARVESTING PROTEIN COMPLEXES of plants. Dietary lutein accumulates in the MACULA LUTEA.. xanthophyll : A subclass of carotenoids consisting of the oxygenated carotenes.	2.81	3	0	carotenol	food colouring; plant metabolite
azadirachtin azadirachtin A : A member of the family of azadirachtins that is isolated from the neem tree (Azadirachta indica).. azadirachtin : A family of terpenoids isolated from the neem tree (Azadirachta indica).	2.77	3	0	acetate ester; azadirachtin; cyclic hemiketal; enoate ester; epoxide; methyl ester; organic heterotetracyclic compound; secondary alcohol; tertiary alcohol	hepatoprotective agent
cucurbitacin c cucurbitacin C: structure in first source	2.25	1	0	cucurbitacin
genistin genistin: glycoside of soy bean isoflavone, gentistein	2.77	3	0	7-hydroxyisoflavones 7-O-beta-D-glucoside
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.	2.02	1	0	cycloalkatriene; diterpene; macrocycle	animal metabolite; bacterial metabolite; coral metabolite
7-hydroxycoumarin 7-oxycoumarin: derivatives have anti-oxidant properties. umbelliferone : A hydroxycoumarin that is coumarin substituted by a hydroxy group ay position 7.	2.02	1	0	hydroxycoumarin	fluorescent probe; food component; plant metabolite
alpha-farnesene alpha-farnesene: structure given in first source. alpha-farnesene : A farnesene that is 1,3,6,10-tetraene substituted by methyl groups at positions 3, 7 and 11 respectively.. farnesene : A sesquiterpene that is any of the four possible isomers of 3,7,11-trimethyl-1,3,6,10-dodecatetraene (alpha-farnesene) or of the two possible isomers of 7,11-dimethyl-3-methylene-1,6,10-dodecatriene.	3.22	5	0	alpha-farnesene
humulene humulene: structure given in first source. (1E,4E,8E)-alpha-humulene : The (1E,4E,8E)-isomer of alpha-humulene.	3.94	12	0	alpha-humulene
oleuropein oleuropein: iridoid isolated from leaves and fruit of Olea and Ligustrum (Oleaceae). oleuropein : A secoiridoid glycoside that is the methyl ester of 3,4-dihydro-2H-pyran-5-carboxylic acid which is substituted at positions 2, 3, and 4 by hydroxy, ethylidene, and carboxymethyl groups, respectively and in which the anomeric hydroxy group at position 2 has been converted into its beta-D-glucoside and the carboxylic acid moiety of the carboxymethyl substituent has been converted to the corresponding 3,4-dihydroxyphenethyl ester (the 2S,3E,4S stereoisomer). The most important phenolic compound present in olive cultivars.	5.2	2	1	beta-D-glucoside; catechols; diester; methyl ester; pyrans; secoiridoid glycoside	anti-inflammatory agent; antihypertensive agent; antineoplastic agent; antioxidant; apoptosis inducer; NF-kappaB inhibitor; nutraceutical; plant metabolite; radical scavenger
zearalenone Zearalenone: (S-(E))-3,4,5,6,8,10-Hexahydro-14,16-dihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione. One of a group of compounds known under the general designation of resorcylic acid lactones. Cis, trans, dextro and levo forms have been isolated from the fungus Gibberella zeae (formerly Fusarium graminearum). They have estrogenic activity, cause toxicity in livestock as feed contaminant, and have been used as anabolic or estrogen substitutes.. zearalenone : A macrolide comprising a fourteen-membered lactone fused to 1,3-dihydroxybenzene; a potent estrogenic metabolite produced by some Giberella species.	1.95	1	0	macrolide; resorcinols	fungal metabolite; mycoestrogen
baicalein [no description available]	2.1	1	0	trihydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antibacterial agent; anticoronaviral agent; antifungal agent; antineoplastic agent; antioxidant; apoptosis inducer; EC 1.13.11.31 (arachidonate 12-lipoxygenase) inhibitor; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; EC 4.1.1.17 (ornithine decarboxylase) inhibitor; ferroptosis inhibitor; geroprotector; hormone antagonist; plant metabolite; prostaglandin antagonist; radical scavenger
fisetin [no description available]	2.08	1	0	3'-hydroxyflavonoid; 7-hydroxyflavonol; tetrahydroxyflavone	anti-inflammatory agent; antioxidant; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; geroprotector; metabolite; plant metabolite
hispidulin hispidulin : A monomethoxyflavone that is scutellarein methylated at position 6.	2.03	1	0	monomethoxyflavone; trihydroxyflavone	anti-inflammatory agent; anticonvulsant; antineoplastic agent; antioxidant; apoptosis inducer; plant metabolite
hyperoside quercetin 3-O-beta-D-galactopyranoside : A quercetin O-glycoside that is quercetin with a beta-D-galactosyl residue attached at position 3. Isolated from Artemisia capillaris, it exhibits hepatoprotective activity.	2.13	1	0	beta-D-galactoside; monosaccharide derivative; quercetin O-glycoside; tetrahydroxyflavone	hepatoprotective agent; plant metabolite
3-methylquercetin isorhamnetin : A monomethoxyflavone that is quercetin in which the hydroxy group at position 3' is replaced by a methoxy group.	3.16	5	0	7-hydroxyflavonol; monomethoxyflavone; tetrahydroxyflavone	anticoagulant; EC 1.14.18.1 (tyrosinase) inhibitor; metabolite
morusin morusin: from Morus root bark; structure given in first source. morusin : An extended flavonoid that is flavone substituted by hydroxy groups at positions 5, 2' and 4', a prenyl group at position 3 and a 2,2-dimethyl pyran group across positions 7 and 8.	4.9	1	1	extended flavonoid; trihydroxyflavone	antineoplastic agent; plant metabolite
myricetin [no description available]	2.05	1	0	7-hydroxyflavonol; hexahydroxyflavone	antineoplastic agent; antioxidant; cyclooxygenase 1 inhibitor; food component; geroprotector; hypoglycemic agent; plant metabolite
rhamnetin rhamnetin: aglycone of xanthorhamnin; from Rhamnus. rhamnetin : A monomethoxyflavone that is quercetin methylated at position 7.	2.41	1	0	monomethoxyflavone; tetrahydroxyflavone	anti-inflammatory agent; antioxidant; metabolite
wogonin wogonin: structure in first source. wogonin : A dihydroxy- and monomethoxy-flavone in which the hydroxy groups are positioned at C-5 and C-7 and the methoxy group is at C-8.	2.1	1	0	dihydroxyflavone; monomethoxyflavone	angiogenesis inhibitor; antineoplastic agent; cyclooxygenase 2 inhibitor; plant metabolite
daidzein [no description available]	2.77	3	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
trans-2,3',4,5'-tetrahydroxystilbene trans-2,3',4,5'-tetrahydroxystilbene: hydroxystilbene oxyresveratrol	2.21	1	0	stilbenoid
pterostilbene [no description available]	2.07	1	0	diether; methoxybenzenes; stilbenol	anti-inflammatory agent; antineoplastic agent; antioxidant; apoptosis inducer; hypoglycemic agent; neuroprotective agent; neurotransmitter; plant metabolite; radical scavenger
epsilon-viniferin epsilon-viniferin: stilbene dimer; isolated from the Oriental medicinal plant Vitis coignetiae; structure given in first source. (-)-trans-epsilon-viniferin : A stilbenoid that is the (-)-trans-stereoisomer of epsilon-viniferin, obtained by cyclodimerisation of trans-resveratrol.	3.02	4	0	1-benzofurans; polyphenol; stilbenoid	metabolite
chicoric acid chicoric acid: inhibits HIV-1 integrase	2.41	1	0	organooxygen compound	geroprotector; HIV-1 integrase inhibitor
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.	6.77	17	1	rosmarinic acid	geroprotector; plant metabolite
salvianolic acid a salvianolic acid A: a nootropic depside from Salvia miltiorrhizia	2.83	3	0	stilbenoid
feruloylputrescine feruloylputrescine: structure given in first source	2.25	1	0	hydroxycinnamic acid
acteoside acteoside: a protein kinase C inhibitor with hepatoprotective, anti-asthmatic, and analgesic activities; a phenylethanoid glycoside related to isoacteoside; from leaves of Lippia multiflora (Verbenaceae). acteoside : A glycoside that is the alpha-L-rhamnosyl-(1->3)-beta-D-glucoside of hydroxytyrosol in which the hydroxy group at position 4 of the glucopyranosyl moiety has undergone esterification by formal condensation with trans-caffeic acid.	4.11	4	0	catechols; cinnamate ester; disaccharide derivative; glycoside; polyphenol	anti-inflammatory agent; antibacterial agent; antileishmanial agent; neuroprotective agent; 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.	2.17	1	0	aromatic ketone; benzenetriol; chromenol; enone; methyl ketone	anti-allergic agent; antihypertensive agent; antineoplastic agent; apoptosis inducer; K-ATP channel agonist; metabolite
ellagic acid [no description available]	2.13	1	0	catechols; cyclic ketone; lactone; organic heterotetracyclic compound; polyphenol	antioxidant; EC 1.14.18.1 (tyrosinase) inhibitor; EC 2.3.1.5 (arylamine N-acetyltransferase) inhibitor; EC 2.4.1.1 (glycogen phosphorylase) inhibitor; EC 2.5.1.18 (glutathione transferase) inhibitor; EC 2.7.1.127 (inositol-trisphosphate 3-kinase) inhibitor; EC 2.7.1.151 (inositol-polyphosphate multikinase) inhibitor; EC 2.7.4.6 (nucleoside-diphosphate kinase) inhibitor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; EC 5.99.1.2 (DNA topoisomerase) inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; food additive; fungal metabolite; geroprotector; plant metabolite; skin lightening agent
ginkgolic acid [no description available]	2.06	1	0	hydroxybenzoic acid
prostaglandin a1 [no description available]	3.29	6	0	prostaglandins A
anandamide anandamide : An N-acylethanolamine 20:4 resulting from the formal condensation of carboxy group of arachidonic acid with the amino group of ethanolamine.	7.08	1	0	endocannabinoid; N-acylethanolamine 20:4	human blood serum metabolite; neurotransmitter; vasodilator agent
cerulenin Cerulenin: An epoxydodecadienamide isolated from several species, including ACREMONIUM, Acrocylindrum, and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function.. cerulenin : An epoxydodecadienamide isolated from several species, including Acremonium, Acrocylindrum and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function.	2.39	2	0	epoxide; monocarboxylic acid amide	antifungal agent; antiinfective agent; antilipemic drug; antimetabolite; antimicrobial agent; fatty acid synthesis inhibitor
astragalin kaempferol-3-O-glucoside: isolated from the pit of Mahkota dewa; structure in first source. kaempferol 3-O-beta-D-glucoside : A kaempferol O-glucoside in which a glucosyl residue is attached at position 3 of kaempferol via a beta-glycosidic linkage.	2.02	1	0	beta-D-glucoside; kaempferol O-glucoside; monosaccharide derivative; trihydroxyflavone	plant metabolite; trypanocidal drug
alpha-ionone alpha-ionone: RN given refers to cpd without isomeric designation; structure	2.21	1	0	enone; ionone; methyl ketone
iobenguane (131i) 3-((aminoiminomethyl)thio)-2-propenoic acid: potent agonist at GABA-receptors; RN given refers to (Z)-isomer; RN for cpd without isomeric designation not available 3/89	3.08	1	0
8-epi-prostaglandin f2alpha 8-epi-prostaglandin F2alpha: a potent preglomerular vasoconstrictor acting principally through thromboxane A2 receptor activation. 8-epi-prostaglandin F2alpha : An isoprostane that is prostaglandin F2alpha having inverted stereochemistry at the 8-position.	2.43	2	0	F2-isoprostane	biomarker; bronchoconstrictor agent; vasoconstrictor agent
tocotrienol, alpha alpha-tocotrienol : A tocotrienol that is chroman-6-ol substituted by methyl groups at positions 2, 5, 7 and 8 and a farnesyl chain at position 2. It has been found in palm oil derived from Elaeis guineensis.	2.11	1	0	tocotrienol; vitamin E	ferroptosis inhibitor; human metabolite; neuroprotective agent; plant metabolite
zinostatin Zinostatin: An enediyne that alkylates DNA and RNA like MITOMYCIN does, so it is cytotoxic.	2.42	2	0
9-hydroperoxy-11,12-octadecadienoic acid 9-hydroperoxy-11,12-octadecadienoic acid: RN refers to (E,E)-isomer	2.97	4	0	hydroperoxy polyunsaturated fatty acid; octadecadienoic acid
9-hydroxy-10,12-octadecadienoic acid 9-hydroxy-10,12-octadecadienoic acid: RN given refers to unspecified stereoisomer. 9-HODE : A HODE that consists of (10E,12Z)-octadecadienoic acid with the hydroxy substituent located at position 9.	2.42	2	0	HODE; octadecadienoic acid	human metabolite; metabolite; mouse metabolite; plant metabolite
13-hydroxy-9,11-octadecadienoic acid 13-hydroxy-9,11-octadecadienoic acid: chemorepellant factor which maintains blood vessel wall thromboresistance; RN given refers to unspecified stereoisomer	2.47	2	0	octadecadienoic acid
thromboxane b2 Thromboxane B2: A stable, physiologically active compound formed in vivo from the prostaglandin endoperoxides. It is important in the platelet-release reaction (release of ADP and serotonin).. thromboxane B2 : A member of the class of thromboxanes B that is (5Z,13E)-thromboxa-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15.	2	1	0	thromboxanes B	human metabolite; mouse metabolite
4-hydroxy-2-hexenal 4-hydroxy-2-hexenal: metabolite from senecionine; RN given refers to cpd without isomeric designation	2	1	0	fatty aldehyde
2,4-heptadienal 2,4-heptadienal: structure in first source. (E,E)-hepta-2,4-dienal : A heptadienal in which the two double bonds are located at positions 2 and 4 (the E,E-geoisomer).	2.1	1	0	heptadienal	flavouring agent
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.	3.8	3	0	4-hydroxynon-2-enal; 4-hydroxynonenal
ubiquinone 8 [no description available]	4.9	1	1	ubiquinones	biomarker
sphingosine 1-phosphate sphingosine 1-phosphate: RN given refers to (R-(R,S-(E)))-isomer; RN for cpd without isomeric designation not available 8/89. sphingosine 1-phosphate : A phosphosphingolipid that consists of sphingosine having a phospho group attached at position 1	3.03	4	0	sphingoid 1-phosphate	mouse metabolite; signalling molecule; sphingosine-1-phosphate receptor agonist; T-cell proliferation inhibitor; vasodilator agent
codeine [no description available]	3.04	5	0	morphinane alkaloid; organic heteropentacyclic compound	antitussive; drug allergen; environmental contaminant; opioid analgesic; opioid receptor agonist; prodrug; xenobiotic
beta-nitrostyrene beta-nitrostyrene: RN given refers to cpd without isomeric designation	2.07	1	0
cyproterone Cyproterone: An anti-androgen that, in the form of its acetate (CYPROTERONE ACETATE), also has progestational properties. It is used in the treatment of hypersexuality in males, as a palliative in prostatic carcinoma, and, in combination with estrogen, for the therapy of severe acne and hirsutism in females.	3.05	1	0	17alpha-hydroxy steroid; 20-oxo steroid; 3-oxo-Delta(4) steroid; chlorinated steroid; tertiary alpha-hydroxy ketone	androgen antagonist
levetiracetam Levetiracetam: A pyrrolidinone and acetamide derivative that is used primarily for the treatment of SEIZURES and some movement disorders, and as a nootropic agent.. levetiracetam : A pyrrolidinone and carboxamide that is N-methylpyrrolidin-2-one in which one of the methyl hydrogens is replaced by an aminocarbonyl group, while another is replaced by an ethyl group (the S enantiomer). An anticonvulsant, it is used for the treatment of epilepsy in both human and veterinary medicine.	2.06	1	0	pyrrolidin-2-ones	anticonvulsant; environmental contaminant; xenobiotic
nalmefene nalmefene: RN given refers to 5-alpha isomer	3.27	1	0	morphinane alkaloid
naloxone Naloxone: A specific opiate antagonist that has no agonist activity. It is a competitive antagonist at mu, delta, and kappa opioid receptors.. naloxone : A synthetic morphinane alkaloid that is morphinone in which the enone double bond has been reduced to a single bond, the hydrogen at position 14 has been replaced by a hydroxy group, and the methyl group attached to the nitrogen has been replaced by an allyl group. A specific opioid antagonist, it is used (commonly as its hydrochloride salt) to reverse the effects of opioids, both following their use of opioids during surgery and in cases of known or suspected opioid overdose.	2.74	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.	2.04	1	0	phylloquinones; vitamin K	cofactor; human metabolite; plant metabolite
sirolimus Sirolimus: A macrolide compound obtained from Streptomyces hygroscopicus that acts by selectively blocking the transcriptional activation of cytokines thereby inhibiting cytokine production. It is bioactive only when bound to IMMUNOPHILINS. Sirolimus is a potent immunosuppressant and possesses both antifungal and antineoplastic properties.. sirolimus : A macrolide lactam isolated from Streptomyces hygroscopicus consisting of a 29-membered ring containing 4 trans double bonds, three of which are conjugated. It is an antibiotic, immunosupressive and antineoplastic agent.	2.57	2	0	antibiotic antifungal drug; cyclic acetal; cyclic ketone; ether; macrolide lactam; organic heterotricyclic compound; secondary alcohol	antibacterial drug; anticoronaviral agent; antineoplastic agent; bacterial metabolite; geroprotector; immunosuppressive agent; mTOR inhibitor
brefeldin a [no description available]	13.29	848	0	macrolide antibiotic	Penicillium metabolite
alvocidib alvocidib: structure given in first source. alvocidib : A synthetic dihydroxyflavone that is 5,7-dihydroxyflavone which is substituted by a 3-hydroxy-1-methylpiperidin-4-yl group at position 8 and by a chlorine at the 2' position (the (-)-3S,4R stereoisomer). A cyclin-dependent kinase 9 (CDK9) inhibitor, it has been studied for the treatment of acute myeloid leukaemia, arthritis and atherosclerotic plaque formation.	3.31	1	0	dihydroxyflavone; hydroxypiperidine; monochlorobenzenes; tertiary amino compound	antineoplastic agent; antirheumatic drug; apoptosis inducer; EC 2.7.11.22 (cyclin-dependent kinase) inhibitor
morphine Meconium: The thick green-to-black mucilaginous material found in the intestines of a full-term fetus. It consists of secretions of the INTESTINAL GLANDS; BILE PIGMENTS; FATTY ACIDS; AMNIOTIC FLUID; and intrauterine debris. It constitutes the first stools passed by a newborn.	5.11	14	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
pactamycin Pactamycin: Antibiotic produced by Streptomyces pactum used as an antineoplastic agent. It is also used as a tool in biochemistry because it inhibits certain steps in protein synthesis.	8.34	6	0
cgp 62349 [no description available]	2.04	1	0
ah 13205 AH 13205: an EP(2) receptor agonist and leukotriene B4 antagonist	2.02	1	0
cicaprost cicaprost: RN given refers to (3aS-(2E,3aalpha,4alpha(3R,4R),5beta,6aalpha))-isomer	2	1	0	monoterpenoid
dexmedetomidine [no description available]	2.06	1	0	medetomidine	alpha-adrenergic agonist; analgesic; non-narcotic analgesic; sedative
preclamol preclamol: centrally acting dopamine receptor agonist with selectivity for autoreceptors	2.68	3	0
15-deoxy-delta(12,14)-prostaglandin j2 15-deoxy-delta(12,14)-prostaglandin J2: 15-deoxy-PGJ2 is also available; check for double bonds (indicated by delta) at 12 and 14 positions. 15-deoxy-Delta(12,14)-prostaglandin J2 : A prostaglandin J derivative comprising prostaglandin J2 lacking the 15-hydroxy group and having C=C double bonds at the 12- and 14-positions.	5.72	26	0	prostaglandins J	electrophilic reagent; insulin-sensitizing drug; metabolite
ono-ae1-329 ONO-AE1-329: a 16-(m-methoxymethyl)phenyl derivative	2.76	3	0
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.	2.39	2	0	1-O-acyl-sn-glycero-3-phosphocholine
mdl 100907 Serotonin 5-HT2 Receptor Antagonists: Drugs that bind to but do not activate SEROTONIN 5-HT2 RECEPTORS, thereby blocking the actions of SEROTONIN or SEROTONIN 5-HT2 RECEPTOR AGONISTS. Included under this heading are antagonists for one or more specific 5-HT2 receptor subtypes.	2.05	1	0
cytochalasin b Cytochalasin B: A cytotoxic member of the CYTOCHALASINS.. cytochalasin B : An organic heterotricyclic compound, that is a mycotoxin which is cell permeable an an inhibitor of cytoplasmic division by blocking the formation of contractile microfilaments.	3.49	8	0	cytochalasin; lactam; lactone; organic heterotricyclic compound	actin polymerisation inhibitor; metabolite; mycotoxin; platelet aggregation inhibitor
octadecadienoic acid octadecadienoic acid: location of unsaturation not specified. octadecadienoate : A long-chain, unsaturated fatty acid anion formed by deprotonation of the carboxy group of any octadecadienoic acid; major species at pH 7.3.. octadecadienoic acid : Any straight-chain, C18 polyunsaturated fatty acid having two C=C double bonds.	2.8	3	0
stearidonic acid [no description available]	2.13	1	0	long-chain fatty acid; octadecatetraenoic acid; omega-3 fatty acid	Daphnia galeata metabolite; mouse metabolite; plant metabolite
1,2-oleoylphosphatidylcholine 1,2-oleoylphosphatidylcholine: RN given refers to (Z,Z)-isomer. dioleoyl phosphatidylcholine : A phosphatidylcholine in which the phosphatidyl acyl groups are both oleoyl.	1.98	1	0	phosphatidylcholine(1+)
biliverdine [no description available]	2.74	3	0
cinnamyl alcohol cinnamyl alcohol: RN given refers to parent cpd without isomeric designation. (E)-cinnamyl alcohol : The E (trans) stereoisomer of cinnamyl alcohol.. cinnamyl alcohol : A primary alcohol comprising an allyl core with a hydroxy substituent at the 1-position and a phenyl substituent at the 3-position (geometry of the C=C bond unspecified).	2.02	1	0	cinnamyl alcohol	plant metabolite
alpha-cuparenone alpha-cuparenone: structure in first source	2.02	1	0
beta-farnesene beta-farnesene: structure given in first source	2.41	2	0	beta-farnesene
calycosin-7-o-beta-d-glucopyranoside calycosin-7-O-beta-D-glucoside: from Radix Astragali. calycosin-7-O-beta-D-glucoside : A glycosyloxyisoflavone that is calycosin substituted by a beta-D-glucopyranosyl residue at position at 7 via a glycosidic linkage.	2.1	1	0	4'-methoxyisoflavones; 7-hydroxyisoflavones 7-O-beta-D-glucoside; hydroxyisoflavone; monosaccharide derivative
iridal iridal: a plant triterpenoid; structure in first source	2.58	2	0
andrographolide [no description available]	3.08	4	0	carbobicyclic compound; gamma-lactone; labdane diterpenoid; primary alcohol; secondary alcohol	anti-HIV agent; anti-inflammatory drug; antineoplastic agent; metabolite
kaempferol-3-o-rutinoside kaempferol-3-O-rutinoside: isolated from the methanolic extract of the whole plants of Diodia teres through repeated silica gel and Sephadex LH-20 column chromatography; structure in first source. kaempferol-3-rutinoside : A kaempferol O-glucoside that is kaempferol attached to a rutinosyl [6-deoxy-alpha-L-mannosyl-(1->6)-beta-D-glucosyl] residue at position 3 via a glycosidic linkage. It has been isolated from the leaves of Solanum campaniforme.	2.02	1	0	disaccharide derivative; kaempferol O-glucoside; rutinoside; trihydroxyflavone	metabolite; plant metabolite; radical scavenger
nerolidol nerolidol: sesquiterpene; RN given refers to cpd without isomeric designation; nerol is also available. nerolidol : A farnesane sesquiterpenoid that is dodeca-1,6,10-triene which carries methyl groups at positions 3, 7 and 11 and a hydroxy group at position 3. It is a natural product that is present in various flowers and plants with a floral odor. Chemically, it exists in two geometric isomers, trans and cis forms. It is widely used in cosmetics (e.g. shampoos and perfumes), in non-cosmetic products (e.g. detergents and cleansers) and also as a food flavoring agent.. (6Z)-nerolidol : A nerolidol in which the double bond at position 6 adopts a cis-configuration.	3.03	4	0	nerolidol
beta-ocimene beta-ocimene : The trans-stereoisomer of ocimene.. (Z)-beta-ocimene : A beta-ocimene that consists of octa-1,3,6-triene bearing two methyl substituents at positions 3 and 7 (the 3Z-isomer).	3.56	8	0	beta-ocimene	plant metabolite
taxuyunnanine c [no description available]	3.53	8	0	taxane diterpenoid
caryophyllene caryophyllene: RN given refers to cpd without isomeric designation; structure given in first source	4.32	18	0
1-(4-(6-bromobenzo(1,3)dioxol-5-yl)-3a,4,5,9b-tetrahydro-3h-cyclopenta(c)quinolin-8-yl)ethanone 1-(4-(6-bromobenzo(1,3)dioxol-5-yl)-3a,4,5,9b-tetrahydro-3H-cyclopenta(c)quinolin-8-yl)ethanone: G-1 was able to induce both c-fos expression and proliferation in the ERalpha-negative/GPR30-positive SKBR3 breast cancer cells, the requirement for ERalpha expression in GPR30/EGFR signaling may depend on the specific cellular context of different tumor types	7.35	126	0	agonist
thebaine Thebaine: A drug that is derived from opium, which contains from 0.3-1.5% thebaine depending on its origin. It produces strychnine-like convulsions rather than narcosis. It may be habit-forming and is a controlled substance (opiate) listed in the U.S. Code of Federal Regulations, Title 21 Part 1308.12 (1985). (From Merck Index, 11th ed)	2.87	3	0	morphinane alkaloid; organic heteropentacyclic compound
7,8-dimethylalloxazine 7,8-dimethylalloxazine: structure. 7,8-dimethylisoalloxazine : A 7,8-dimethylbenzo[g]pteridine-2,4-dione that is isoalloxazine substituted by methyl groups at positions 7 and 8.. lumichrome : A compound showing blue fluorescence, formed by a photolysis of riboflavin in acid or neutral solution.	2.17	1	0	7,8-dimethylbenzo[g]pteridine-2,4-dione	plant metabolite
casein kinase ii Casein Kinase II: A ubiquitous casein kinase that is comprised of two distinct catalytic subunits and dimeric regulatory subunit. Casein kinase II has been shown to phosphorylate a large number of substrates, many of which are proteins involved in the regulation of gene expression.	2.95	4	0
ag-490 [no description available]	2.08	1	0	catechols; enamide; monocarboxylic acid amide; nitrile; secondary carboxamide	anti-inflammatory agent; antioxidant; apoptosis inducer; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; geroprotector; STAT3 inhibitor
sclareolide sclareolide: has antineoplastic activity; synthesized by oxidation of sclareol; a minor constituent of Arnica angustifolia and Sideritis nutans; structure in first source	2.01	1	0
fosbretabulin fosbretabulin: a microtubule destabilizing agent isolated from Combretum caffrum; structure in first source	2.51	2	0
lead Lead: A soft, grayish metal with poisonous salts; atomic number 82, atomic weight 207.2, symbol Pb.	4.73	9	0	carbon group element atom; elemental lead; metal atom	neurotoxin
tin [no description available]	3.48	2	0	carbon group element atom; elemental tin; metal atom	micronutrient
3-hexenylacetate 3-hexenylacetate: RN refers to (Z)-isomer	3.44	7	0	carboxylic ester
bay 11-7082 (E)-3-tosylacrylonitrile : A nitrile that is acrylonitrile in which the hydrogen located beta,trans to the cyano group is replaced by a tosyl group. It is an inhibitor of cytokine-induced IkappaB-alpha phosphorylation in cells.	2.81	3	0	nitrile; sulfone	apoptosis inducer; EC 2.7.11.10 (IkappaB kinase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; non-steroidal anti-inflammatory drug; platelet aggregation inhibitor
diamide Diamide: A sulfhydryl reagent which oxidizes sulfhydryl groups to the disulfide form. It is a radiation-sensitizing agent of anoxic bacterial and mammalian cells.	2.68	3	0	1,1'-azobis(N,N-dimethylformamide)
15-hydroxy-11 alpha,9 alpha-(epoxymethano)prosta-5,13-dienoic acid 15-Hydroxy-11 alpha,9 alpha-(epoxymethano)prosta-5,13-dienoic Acid: A stable prostaglandin endoperoxide analog which serves as a thromboxane mimetic. Its actions include mimicking the hydro-osmotic effect of VASOPRESSIN and activation of TYPE C PHOSPHOLIPASES. (From J Pharmacol Exp Ther 1983;224(1): 108-117; Biochem J 1984;222(1):103-110)	2.06	1	0
antimony Antimony: A metallic element that has the atomic symbol Sb, atomic number 51, and atomic weight 121.75. It is used as a metal alloy and as medicinal and poisonous salts. It is toxic and an irritant to the skin and the mucous membranes.	2.03	1	0	metalloid atom; pnictogen
cesium Cesium: A member of the alkali metals. It has an atomic symbol Cs, atomic number 50, and atomic weight 132.91. Cesium has many industrial applications, including the construction of atomic clocks based on its atomic vibrational frequency.	2.01	1	0	alkali metal atom
barium Barium: An element of the alkaline earth group of metals. It has an atomic symbol Ba, atomic number 56, and atomic weight 138. All of its acid-soluble salts are poisonous.	2.88	4	0	alkaline earth metal atom; elemental barium
7,8-dihydroxy-4-methylcoumarin 7,8-dihydroxy-4-methylcoumarin: possess strong antioxidant and radical scavenging activities; structure in first source	2	1	0	hydroxycoumarin
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.	2.04	1	0	alkali metal atom
aluminum Aluminum: A metallic element that has the atomic number 13, atomic symbol Al, and atomic weight 26.98.	6.42	23	0	boron group element atom; elemental aluminium; metal atom
levorphanol Levorphanol: A narcotic analgesic that may be habit-forming. It is nearly as effective orally as by injection.	3.47	2	0	morphinane alkaloid
strontium Strontium: An element of the alkaline earth family of metals. It has the atomic symbol Sr, atomic number 38, and atomic weight 87.62.	2.39	2	0	alkaline earth metal atom
bismuth Bismuth: A metallic element that has the atomic symbol Bi, and atomic number 83. Its principal isotope is Bismuth 209.	5.45	4	1	metal atom; pnictogen
thallium Thallium: A heavy, bluish white metal, atomic number 81, atomic weight [204.382; 204.385], symbol Tl.. thallium : A metallic element first identified and named from the brilliant green line in its flame spectrum (from Greek thetaalphalambdalambdaomicronsigma, a green shoot).	7.64	3	0	boron group element 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)	4.91	11	0	metalloid atom; pnictogen	micronutrient
indium Indium: A metallic element, atomic number 49, atomic weight 114.818, symbol In. It is named from its blue line in the spectrum.. indium atom : A metallic element first identified and named from the brilliant indigo (Latin indicum) blue line in its flame spectrum.	4.36	6	0	boron group element atom
naltrexone Naltrexone: Derivative of noroxymorphone that is the N-cyclopropylmethyl congener of NALOXONE. It is a narcotic antagonist that is effective orally, longer lasting and more potent than naloxone, and has been proposed for the treatment of heroin addiction. The FDA has approved naltrexone for the treatment of alcohol dependence.. naltrexone : An organic heteropentacyclic compound that is naloxone substituted in which the allyl group attached to the nitrogen is replaced by a cyclopropylmethyl group. A mu-opioid receptor antagonist, it is used to treat alcohol dependence.	3.27	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.	6.75	18	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.	3.49	2	0	morphinane alkaloid
gallium Gallium: A rare, metallic element designated by the symbol, Ga, atomic number 31, and atomic weight 69.72.. gallium atom : A metallic element predicted as eka-aluminium by Mendeleev in 1870 and discovered by Paul-Emile Lecoq de Boisbaudran in 1875. Named in honour of France (Latin Gallia) and perhaps also from the Latin gallus cock, a translation of Lecoq.	5.01	2	1	boron group element atom
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.	3.52	2	0	dipeptide	EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor
benazepril benazepril: structure given in first source. benazepril : A benzazepine that is benazeprilat in which the carboxy group of the 2-amino-4-phenylbutanoic acid moiety has been converted to the corresponding ethyl ester. It is used (generally as its hydrochloride salt) as a prodrug for the angiotensin-converting enzyme inhibitor benazeprilat in the treatment of hypertension and heart failure.	3.06	1	0	benzazepine; dicarboxylic acid monoester; ethyl ester; lactam	EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; prodrug
ramipril Ramipril: A long-acting angiotensin-converting enzyme inhibitor. It is a prodrug that is transformed in the liver to its active metabolite ramiprilat.. ramipril : A dipeptide that is the prodrug for ramiprilat, the active metabolite obtained by hydrolysis of the ethyl ester group. An angiotensin-converting enzyme (ACE) inhibitor, used to treat high blood pressure and congestive heart failure.. quark : Quarks comprise one of two classes of the fundamental particles. Quarks possess fractional electric charges and are not observed in free state. The word "quark" first appears in James Joyce's Finnegans Wake and has been chosen by Murray Gell-Mann as a name for fundamental building blocks of particles.	3.06	1	0	azabicycloalkane; cyclopentapyrrole; dicarboxylic acid monoester; dipeptide; ethyl ester	bradykinin receptor B2 agonist; cardioprotective agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; matrix metalloproteinase inhibitor; prodrug
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.	5.56	22	0	chalcogen; nonmetal atom	macronutrient
zimeldine Zimeldine: One of the SEROTONIN UPTAKE INHIBITORS formerly used for depression but was withdrawn worldwide in September 1983 because of the risk of GUILLAIN-BARRE SYNDROME associated with its use. (From Martindale, The Extra Pharmacopoeia, 29th ed, p385)	1.97	1	0	styrenes
musk musk: pure essence from secretion of preputial follicles of Moschus moschiferus L.	2.01	1	0	macrolide
2,3-oxidosqualene 2,3-oxidosqualene: an oxidized derivative of SQUALENE that can fold in several ways: chair-boat-chair-boat to LANOSTEROL; chair-chair-chair-boat to dammarane; or all chair to hopane and on to cycloartenol; RN given refers to (all-Z)-isomer. 2,3-epoxysqualene : A squalene triterpenoid obtained by formal epoxidation across the 2,3 C=C bond of squalene.	2.91	3	0	epoxide; squalene triterpenoid
alloocimene alloocimene: representative of carotenoid polyenes; RN given refers to cpd without isomeric designation. (4E,6E)-2,6-dimethylocta-2,4,6-triene : An ocimene that consists of octa-2,4,6-triene bearing methyl substituents at positions 2 and 6 (the 4E,6E-isomer).	2.21	1	0	ocimene	semiochemical
alpha-isomethylionone alpha-isomethylionone: structure in first source	2.02	1	0	sesquiterpenoid
germacrene d germacrene D: RN in 9th CI Form Index for unspecified stereoisomer: 37839-63-7	2.45	2	0
pyrrobutamine pyrrobutamine: RN given refers to parent cpd without isomeric designation; structure	1.95	1	0
5-deazaflavin [no description available]	3.06	1	0	pyridopyrimidine
jaceosidin jaceosidin : A trihydroxyflavone that is flavone with hydroxy groups at positions 5, 7 and 4' and methoxy groups at positions 3' and 6. Isolated from Salvia tomentosa and Artemisia asiatica, it exhibits anti-allergic, anti-inflammatory and apoptosis inducing activties.	2.46	2	0	dimethoxyflavone; trihydroxyflavone	anti-allergic agent; anti-inflammatory agent; antineoplastic agent; apoptosis inducer; metabolite
puerarin [no description available]	2.74	3	0	C-glycosyl compound; isoflavonoid
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).	3.46	2	0	dicarboxylic acid monoester; dipeptide	antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; geroprotector; prodrug
catharanthine [no description available]	3.16	5	0	alkaloid ester; bridged compound; methyl ester; monoterpenoid indole alkaloid; organic heteropentacyclic compound; tertiary amino compound
scirpusin a scirpusin A: from the rhizome of Scirpus fluviatilis and Xinjiang wine grape; structure in first soource	2.13	1	0
dimyristoylphosphatidylcholine 1,2-di-O-myristoyl-sn-glycero-3-phosphocholine : A 1,2-diacyl-sn-glycero-3-phosphocholine where the two phosphatidyl acyl groups are specified as tetradecanoyl (myristoyl).. dimyristoyl phosphatidylcholine : A phosphatidylcholine where the phosphatidyl acyl groups are specified as tetradecanoyl (myristoyl).	2.39	2	0	1,2-diacyl-sn-glycero-3-phosphocholine; phosphatidylcholine 28:0; tetradecanoate ester	antigen; mouse metabolite
2,3-oxidosqualene oxidosqualene: structure in first source. (S)-2,3-epoxysqualene : A 2,3-epoxysqualene in which the chiral centre has S configuration. It is converted into lanosterol by lanosterol synthase (EC 5.4.99.7) in a key rate-limiting step in the biosynthesis of chloesterol, steroid hormones, and vitamin D.	2.21	1	0	2,3-epoxysqualene	human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
ecdysterone Ecdysterone: A steroid hormone that regulates the processes of MOLTING or ecdysis in insects. Ecdysterone is the 20-hydroxylated ECDYSONE.. 20-hydroxyecdysone : An ecdysteroid that is ecdysone substituted by a hydroxy group at position 20.	2.44	2	0	14alpha-hydroxy steroid; 20-hydroxy steroid; 22-hydroxy steroid; 25-hydroxy steroid; 2beta-hydroxy steroid; 3beta-sterol; ecdysteroid; phytoecdysteroid	animal metabolite; plant metabolite
deoxyribose [no description available]	2.02	1	0	deoxypentose	human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
fumarates Fumarates: Compounds based on fumaric acid.. fumarate(2-) : A C4-dicarboxylate that is the E-isomer of but-2-enedioate(2-)	2.68	3	0	butenedioate; C4-dicarboxylate	human metabolite; metabolite; Saccharomyces cerevisiae metabolite
beryllium Beryllium: An element with the atomic symbol Be, atomic number 4, and atomic weight 9.01218. Short exposure to this element can lead to a type of poisoning known as BERYLLIOSIS.. beryllium atom : Alkaline earth metal atom with atomic number 4.	3.47	2	0	alkaline earth metal atom; elemental beryllium; metal allergen	adjuvant; carcinogenic agent; epitope
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	4.81	32	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].	5.77	28	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.	6.4	11	1	monoatomic phosphorus; nonmetal atom; pnictogen	macronutrient
boron Boron: A trace element with the atomic symbol B, atomic number 5, and atomic weight [10.806; 10.821]. Boron-10, an isotope of boron, is used as a neutron absorber in BORON NEUTRON CAPTURE THERAPY.	6.22	9	1	boron group element atom; metalloid atom; nonmetal atom	micronutrient
heroin Heroin: A narcotic analgesic that may be habit-forming. It is a controlled substance (opium derivative) listed in the U.S. Code of Federal Regulations, Title 21 Parts 329.1, 1308.11 (1987). Sale is forbidden in the United States by Federal statute. (Merck Index, 11th ed). heroin : A morphinane alkaloid that is morphine bearing two acetyl substituents on the O-3 and O-6 positions. As with other opioids, heroin is used as both an analgesic and a recreational drug. Frequent and regular administration is associated with tolerance and physical dependence, which may develop into addiction. Its use includes treatment for acute pain, such as in severe physical trauma, myocardial infarction, post-surgical pain, and chronic pain, including end-stage cancer and other terminal illnesses.	1.95	1	0	morphinane alkaloid	mu-opioid receptor agonist; opioid analgesic; prodrug
gluconasturtiin gluconasturtiin: hydrolysis yields phenylethyl isothiocyanate; structure in first source. gluconasturtiin : An aralkylglucosinolic acid that consists of 1-thio-beta-D-glucopyranose attached to a 3-phenyl-N-(sulfooxy)propanimidoyl group at the anomeric sulfur.	2.49	2	0	aralkylglucosinolic acid; benzenes
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	2.88	3	0
n-linolenoyl-l-glutamine N-linolenoyl-L-glutamine: an elicitor of plant volatiles, by membrane-associated enzyme(s) in Manduca sexta	2.73	3	0
metaproterenol 1-methoxy-3-indolylmethylglucosinolate: isolated from Moricandia arvensis (Cruciferae); structure given in first source. neoglucobrassicin : An indolyl carbohydrate that is glucobrassicin methoxy substituted at position 1 of the indole moiety.	3.5	7	0
lespenefril lespenefril: RN given refers to (L)-isomer. kaempferol 3,7-di-O-alpha-L-rhamnoside : A glycosyloxyflavone that is kaempferol attached to alpha-L-rhamnopyranosyl residues at positions 3 and 7 respectively via glycosidic linkages. It has been isolated from the aerial parts of Vicia faba and Lotus edulis.	2.13	1	0	alpha-L-rhamnoside; dihydroxyflavone; glycosyloxyflavone; monosaccharide derivative; polyphenol	anti-inflammatory agent; antidepressant; antineoplastic agent; apoptosis inducer; bone density conservation agent; hypoglycemic agent; immunomodulator; plant metabolite
n-acetylsphingosine N-acetylsphingosine: inhibits phospholipase D. N-acetylsphingosine : A N-acylsphingosine that has an acetamido group at position 2.	2.42	2	0	N-acylsphingosine
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.	1.94	1	0	triglyceride	Caenorhabditis elegans metabolite; plant metabolite
bafilomycin a [no description available]	2.39	2	0
abscisic acid Abscisic Acid: Abscission-accelerating plant growth substance isolated from young cotton fruit, leaves of sycamore, birch, and other plants, and from potatoes, lemons, avocados, and other fruits.. (S)-2-trans-abscisic acid : A 2-trans-abscisic acid with (S)-configuration at the chiral centre.. (+)-abscisic acid : The naturally occurring (1'S)-(+) enantiomer of abscisic acid. It is an important sesquiterpenoid plant hormone which acts as a regulator of plant responses to environmental stresses such as drought and cold.	11.8	548	0	2-trans-abscisic acid
n-caproylsphingosine N-(hexanoyl)sphing-4-enine : An N-acylsphingosine consisting of sphing-4-enine bearing a hexanoyl group on nitrogen.	1.99	1	0	N-acylsphingosine
3,3'-dihexyl-2,2'-oxacarbocyanine 3,3'-dihexyl-2,2'-oxacarbocyanine: a fluorescent probe	1.98	1	0
carbocyanines Carbocyanines: Compounds that contain three methine groups. They are frequently used as cationic dyes used for differential staining of biological materials.	2.69	3	0	cyanine dye; organic iodide salt	fluorochrome
quercetin-3'-o-beta-d-glucopyranoside quercetin 3'-O-glucoside: structure in first source	2.13	1	0
viroxime [no description available]	1.99	1	0
germacrene a germacrene A: RN given for (S-(E,E))-isomer; structure in first source	2.02	1	0	germacrene; sesquiterpene
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.	3.88	11	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.	2.66	3	0	ammonium salt; inorganic sulfate salt	fertilizer
caffeoylmalic acid caffeoylmalic acid: from extracts of Chelidonium majus & Corydalis lutea	2.03	1	0	hydroxycinnamic acid
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.	3.32	6	0
4-hydroxy-2-butenoic acid 4-hydroxy-2-butenoic acid: structure given in first source; RN given refers to cpd without isomeric designation	2.15	1	0	hydroxy fatty acid
mastoparan [no description available]	2.7	3	0	mastoparans; peptidyl amide	antimicrobial 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.	3.38	7	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.	4.22	5	0	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.	2.08	1	0	chalcogen; metalloid atom
allylsilane allylsilane: structure in first source	7.5	2	0
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.	2.39	2	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.	1.99	1	0	(6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid
ethyl linolenate ethyl linolenate : A long-chain fatty acid ethyl ester resulting from the formal condensation of the carboxy group of linolenic acid with the hydroxy group of ethanol.	2.03	1	0
cgp 39551 CGP 39551: N-methyl-D-aspartate receptor antagonist; structure given in first source	2.06	1	0
raubasine raubasine: RN given refers to (19alpha)-isomer; structure	3.66	9	0	yohimban alkaloid
dizocilpine maleate Dizocilpine Maleate: A potent noncompetitive antagonist of the NMDA receptor (RECEPTORS, N-METHYL-D-ASPARTATE) used mainly as a research tool. The drug has been considered for the wide variety of neurodegenerative conditions or disorders in which NMDA receptors may play an important role. Its use has been primarily limited to animal and tissue experiments because of its psychotropic effects.. dizocilpine maleate : A maleate salt obtained by reaction of dizocilpine with one equivalent of maleic acid.	7.08	15	1	maleate salt; tetracyclic antidepressant	anaesthetic; anticonvulsant; neuroprotective agent; nicotinic antagonist; NMDA receptor antagonist
pregnanediol [no description available]	1.94	1	0
cadinol cadinol: from callus cultures of Chamomilla recutita (Asteraceae)	2.17	1	0
neramexane [no description available]	8.37	31	1
1-palmitoyl-2-oleoylphosphatidylcholine 1-palmitoyl-2-oleoylphosphatidylcholine: RN given refers to (Z)-isomer	2.05	1	0
vitamin a2 vitamin A2: RN given refers to cpd without isomeric designation. all-trans-3,4-didehydroretinol : A retinoid derived from 3,4-desaturation of the beta-ionone ring of all-trans-retinol.	2.04	1	0	retinoid; vitamin A	human xenobiotic metabolite; marine xenobiotic metabolite; mouse metabolite
latrunculin b latrunculin B: 14-membered macrolide attached to 2-thiazolidinone moiety; from Red Sea sponge Latrunculia magnifica; see also latrunculin A; structure given in first source. latrunculin B : A macrolide consisting of a 14-membered bicyclic lactone attached to the rare 2-thiazolidinone moiety. It is obtained from the Red Sea sponge Latrunculia magnifica.	1.99	1	0	cyclic hemiketal; macrolide; oxabicycloalkane; thiazolidinone	actin polymerisation inhibitor; metabolite; toxin
bafilomycin a1 bafilomycin A1: from Streptomyces griseus; structure given in first source. bafilomycin A1 : The most used of the bafilomycins, a family of toxic macrolide antibiotics derived from Streptomyces griseus.	3.94	13	0	cyclic hemiketal; macrolide antibiotic; oxanes	apoptosis inducer; autophagy inhibitor; bacterial metabolite; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; EC 3.6.3.14 (H(+)-transporting two-sector ATPase) inhibitor; ferroptosis inhibitor; fungicide; potassium ionophore; toxin
aminoethoxyvinylglycine aminoethoxyvinylglycine: RN given for (S-(E))-isomer	2.06	1	0
triticonazole triticonazole: a fungicide triticonazole. triticonazole : A racemate comprising equal amounts of (R)- and (S)-triticonazole. A seed treatment fungicide for the control of common bunt, loose smut and covered smut on barley, oats and wheat.	4.46	18	0
uniconazole uniconazole: structural analog of diniconazole; RN refers to ((E)-(+-))-isomer; structure given in first source. uniconazole : A racemate comprising equimolar amounts of uniconazole-P and its enantiomer, (R)-uniconazole.. (1E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol : A member of the class of triazoles that is 1,2,4-triazole which is substituted at position 1 by a 1-(p-chlorophenyl)-3-hydroxy-4,4-dimethylpent-1-en-2-yl group.	2.04	1	0	monochlorobenzenes; secondary alcohol; triazoles
terrein terrein: from culture solution of fungus, Pestilotiopsis microspora;structure in first source	6.18	39	0	polyol
1-oleoyl-2-acetylglycerol [no description available]	1.97	1	0	1,2-diglyceride
involucrin involucrin: soluble precursor protein of cross-linked envelope characteristic of epidermal s. corneum synthesized by keratinocytes in natural & cultured human epithelia; see also related records for prekeratin & stratum corneum basic protein precursor	2.04	1	0
3-(2-carboxypiperazine-4-yl)-1-propenyl-1-phosphonic acid SDZ EAA 494: N-methyl-D-aspartate receptor antagonist	2.42	2	0
rhizoxin rhizoxin: from Rhizopus chinensis; causal agent of rice seedling blight; structure given in first source. rhizoxin : An macrolide antibiotic isolated from the pathogenic plant fungus Rhizopus microsporus. It also exhibits antitumour and antimitotic activity.	2.08	1	0	1,3-oxazoles; epoxide; macrolide antibiotic	antimitotic; antineoplastic agent; metabolite
asteltoxin asteltoxin: polyenic alpha-pyrone mycotoxin closely related to aurovertins isolated from Aspergillus stellatus; structure given in first source	2.02	1	0	furofuran
concanamycin a concanamycin A: from Streptomyces diastatochromogenes S-45; inhibits vacuolar H+ ATPase. concanamycin A : A concanamycin in which the lactone ring contains 4 double bonds and is substituted by 4 methyl groups, 2 hydroxy groups, 2 methoxy groups and an ethyl group.	1.99	1	0	carbamate ester; concanamycin	antifungal agent; EC 3.6.3.14 (H(+)-transporting two-sector ATPase) inhibitor; metabolite
plastochromanol 8 plastochromanol 8: has antiproliferative activity against 3T3-L1 cells and anti-adipogenic activity; structure; plastochromanol 3 is gamma-tocotrienol	2.15	1	0
thiazole orange thiazole orange: structure given in first source. thiazole orange : A cyanine dye comprising the thiazole orange cation [1-methyl-4-[(3-methyl-1,3-benzothiazol-2(3H)-ylidene)methyl]quinolinium] with the p-tosylate counterion.	2.31	1	0	cyanine dye	fluorochrome
5-(2-iodovinyl)-2'-deoxyuridine 5-(2-iodovinyl)-2'-deoxyuridine: RN given refers to cpd without isomeric designation	1.97	1	0
2,3,5,4'-tetrahydroxystilbene 2-o-glucopyranoside 2,3,5,4'-tetrahydroxystilbene 2-O-glucopyranoside: isolated from dried root tubers of Polygonum multiflorum; structure in first source	2.07	1	0
1-(3-hydroxy-4-(hydroxymethyl)cyclopentyl)-5-(2-iodovinyl)-2,4-(1h,3h)-pyrimidinedione 1-(3-hydroxy-4-(hydroxymethyl)cyclopentyl)-5-(2-iodovinyl)-2,4-(1H,3H)-pyrimidinedione: RN & structure given in first source; RN refers to (E)-isomer	3.22	6	0
9-hydroxy-10,12,15-octadecatrienoic acid 9-hydroxy-10,12,15-octadecatrienoic acid: structure given in first source; RN given refers to (S-(E,Z,Z))-isomer; cpd without isomeric designation not avail 1/90. 9(S)-HOTrE : A 9-HOTrE consisting of (10E,12Z,15Z)-octadecatrienoic acid in which the 9-hydroxy group has S-configuration.	2.01	1	0	9-HOTrE	plant metabolite
4-coumaroyl-coenzyme a 4-coumaroyl-coenzyme A: structure given in first source. trans-4-coumaroyl-CoA : A 4-coumaroyl-CoA in which the double bond of the coumaroyl group has trans-geochemistry.. 4-coumaroyl-CoA : The S-(4-coumaroyl) derivative of coenzyme A.	2.13	1	0	4-coumaroyl-CoA
13-hydroperoxy-9,11,15-octadecatrienoic acid 13-hydroperoxy-9,11,15-octadecatrienoic acid: structure given in first source; RN given refers to (E,Z,Z)-isomer; RN for cpd without isomeric designation not available 11/88	2.31	1	0
picroside i picroside I: RN given for (1aS-(1aalpha,1bbeta,2beta(E),5abeta,6beta,6aalpha))-isomer; hepatoprotective agent; structure in first source	2.08	1	0
valerenic acid valerenic acid: a saturated oplopanone type indene from Valeriana officinalis. valerenic acid : A monocarboxylic acid that is 2-methylprop-2-enoic acid which is substituted at position 3 by a 3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl group. A bicyclic sesquiterpenoid constituent of the essential oil of the Valerian plant.	2.13	1	0	carbobicyclic compound; monocarboxylic acid; sesquiterpenoid	GABA modulator; plant metabolite; sedative; volatile oil component
zeatin riboside zeatin riboside: RN given refers to parent cpd. 9-ribosyl-trans-zeatin : A 9-ribosylzeatin having trans-zeatin as the nucleobase.	3.69	9	0	9-ribosylzeatin; nucleoside analogue	cytokinin; plant metabolite
a 201a A 201A: from Streptomyces capreolus; structure given in first source	2.13	1	0
emerin emerin: a serine-rich protein; responsible for Emery-Dreifuss muscular dystrophy (EDMD)	2.02	1	0
terpestacin terpestacin: structure given in first source; isolated from Arthrinium; inhibits syncytium (giant cell) formation	2.45	2	0	secondary alcohol
mulberroside a mulberroside A: structure in first source	2.55	2	0	glycoside; stilbenoid
tuberonic acid tuberonic acid: RN given for (1R-(1alpha,2alpha(Z)))-isomer; isolated from the potato Solanum tuberosum; structure in first source. tuberonic acid : An oxo monocarboxylic acid that is (+)-7-isojasmonic acid in which one of the hydrogens of the side-chain methyl group is replaced by a hydroxy group.	3.42	7	0	cyclopentanones; homoallylic alcohol; oxo monocarboxylic acid; primary alcohol	jasmonates; plant metabolite
a 315675 [no description available]	3.85	3	0
salvianolic acid B salvianolic acid B: isolated from Salvia miltiorrhiza. salvianolic acid B : A member of the class of 1-benzofurans that is an antioxidant and free radical scavenging compound extracted from S. miltiorrhiza	3.53	7	0	1-benzofurans; catechols; dicarboxylic acid; enoate ester; polyphenol	anti-inflammatory agent; antidepressant; antineoplastic agent; antioxidant; apoptosis inducer; autophagy inhibitor; cardioprotective agent; hepatoprotective agent; hypoglycemic agent; neuroprotective agent; osteogenesis regulator; plant metabolite
prothioconazole prothioconazole: a fungicide. prothioconazole : A racemate comprising equal amounts of (R)- and (S)-prothioconazole. A fungicide for use both as a seed treatment and foliar spray to treat a variety of diseases in cereals.. 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1,2-dihydro-1,2,4-triazole-3-thione : A member of the class of triazoles that is 1,2,4-triazole-3-thione substituted at position 2 by a 2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl group.	2.61	2	0	cyclopropanes; monochlorobenzenes; tertiary alcohol; thiocarbonyl compound; triazoles
oxepins Oxepins: Compounds based on a 7-membered heterocyclic ring including an oxygen. They can be considered a medium ring ether. A natural source is the MONTANOA plant genus. Some dibenzo-dioxepins, called depsidones, are found in GARCINIA plants.	2.02	1	0
sorgoleone sorgoleone: Sorgoleone refers to a group of benzoquinones from Sorghum bicolor having 2-hydroxy and 5-methoxy substitutions and either a 15- or 17-carbon chain with one, two, or three double bonds at position 3; The name sorgoleone was first given to 5-methoxy-3-(8'Z,11'Z)-pentadeca-8'11'14'-trienylbenzene-1,2,4-triol but this is unstable and is easily oxidized to the quinone, sorgoleone-358, which is the major constituent of the root exudate; binds at PLASTOQUINONE site of PSII. sorgoleone : A member of the family of benzoquinones, sorgoleone is 2-hydroxy-5-methoxy-1,4-benzoquinone in which the hydrogen at position 3 is substituted by a (4Z,7Z)-pentadeca-1,4,7-trien-15-yl group.	2.08	1	0	monohydroxy-1,4-benzoquinones
clovamide clovamide: RN given for (Z)-isomer; structure in first source	2	1	0	tyrosine derivative
verlukast verlukast: LTD4 receptor antagonist	1.99	1	0
paclobutrazol paclobutrazol: RN given refers to (R,R)-(+-)-isomer. paclobutrazol : A racemate comprising equimolar amounts of (2R,3R)- and (2S,3S)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pentan-3-ol. It acts as a plant-growth retardant and fungicide via inhibition of gibberellin biosynthesis.	2.74	3	0
beta-escin [no description available]	5.81	27	0
glucoraphanin glucoraphanin: precursor of sulforaphane. glucoraphanin : A thia-glucosinolic acid that is glucoerucin in which the sulfur atom of the methyl thioether group has been oxidised to the corresponding sulfoxide.	2.81	3	0	sulfoxide; thia-alkylglucosinolic acid
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
1-aminocyclopentane-1,3,4-tricarboxylic acid 1-aminocyclopentane-1,3,4-tricarboxylic acid: metabolic glutamate receptor (mGluR) antagonist; structure in first source	8.44	7	0
ro 25-6981 Ro 25-6981: blocks NMDA receptors containg NR2B subunit; structure in first source. Ro 25-6981 : A member of the class of piperidines that is 4-benzylpiperidine substituted by a 3-hydroxy-3-(4-hydroxyphenyl)-2-methylpropyl group at position 1 (the 1R,2S-stereoisomer). It is a potent antagonist of the GluN2B subunit of the N-methyl-D-aspartate (NMDA) receptor.	2.48	2	0	benzenes; phenols; piperidines; secondary alcohol; tertiary amino compound	anticonvulsant; antidepressant; neuroprotective agent; NMDA receptor antagonist
n,n'-dicyclopentyl-2-methylsulfanyl-5-nitro-pyrimidine-4,6-diamine N,N'-dicyclopentyl-2-methylsulfanyl-5-nitro-pyrimidine-4,6-diamine: structure in first source	6.71	41	0	aryl sulfide
lactacystin [no description available]	3.5	8	0	lactam; S-substituted L-cysteine
madecassic acid [no description available]	2.08	1	0
aspidospermidine aspidospermidine: structure in first source	2.05	1	0	Aspidosperma alkaloid; indole alkaloid fundamental parent
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.	2.39	2	0	cyclic ether; enol; polyunsaturated fatty acid; very long-chain fatty acid	calcium ionophore; metabolite
rosaprostol rosaprostol: structure given in first source; RN given refers to parent cpd without isomeric designation	2.39	2	0	prostanoid
pentopril CGS 13945: structure given in first source	3.06	1	0
beraprost beraprost: stable prostacyclin analog; structure given in first source. beraprost : An organic heterotricyclic compound that is (3aS,8bS)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan in which the hydrogens at positions 1R, 2R and 5 are replaced by (3S)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl, hydroxy and 3-carboxypropyl groups, respectively. It is a prostaglandin receptor agonist which is approved to treat pulmonary arterial hypertension in Asia.	2.13	1	0	enyne; monocarboxylic acid; organic heterotricyclic compound; secondary alcohol; secondary allylic alcohol	anti-inflammatory agent; antihypertensive agent; platelet aggregation inhibitor; prostaglandin receptor agonist; vasodilator agent
rhc 3659 pivalopril: structure given in first source	4.17	5	0	N-acyl-amino acid
beta-elemene beta-elemene: increases tumor cell immunogenicity by inducing, at least in part, elevated expression of heat shock protein 70 on tumor cell surface. beta-elemene : A sesquiterpene that consists of cyclohexane bearing methyl and vinyl substituents at position 1 as well as two isopropenyl substituents at positions 2 and 4.. (-)-beta-elemene : The (-)-enantiomer of beta-elemene that has (1S,2S,4R)-configuration.	2.5	2	0	beta-elemene	antineoplastic agent
belinostat [no description available]	2.13	1	0	hydroxamic acid; olefinic compound; sulfonamide	antineoplastic agent; EC 3.5.1.98 (histone deacetylase) inhibitor
rebaudioside a rebaudioside A: glucoside isolated from the leaves of the paraguayan shrub, Stevia rebaudiana; has taste properties superior to stevioside; structure in first source. rebaudioside A : A rebaudioside that is rubusoside in which the hydroxy groups at positions 3 and 4 of the beta-D-glucopyranosyloxy group at the 13alpha position have both been converted to the corresponding beta-D-glucopyranoside.	2.15	1	0	beta-D-glucoside; rebaudioside; tetracyclic diterpenoid	sweetening agent
isoborneol isoborneol: RN given refers to cpd without isomeric designation; structure	1.99	1	0	borneol
bromopyruvate [no description available]	2.25	1	0	2-oxo monocarboxylic acid anion
staurosporine staurosporinium : Conjugate acid of staurosporine.	4.08	15	0	ammonium ion derivative
chloralose Chloralose: A derivative of CHLORAL HYDRATE that was used as a sedative but has been replaced by safer and more effective drugs. Its most common use is as a general anesthetic in animal experiments.	1.98	1	0
farnesiferol a farnesiferol A: from Ferula szowitsiana; structure in first source	2.08	1	0
hypericum Hypericum: Genus of perennial plants in the family CLUSIACEAE (sometimes classified as Hypericaceae). Herbal and homeopathic preparations are used for depression, neuralgias, and a variety of other conditions. Hypericum contains flavonoids; GLYCOSIDES; mucilage, TANNINS; volatile oils (OILS, ESSENTIAL), hypericin and hyperforin.. 6-formamidopenicillanic acid : A penicillanic acid having a (6R)-formamido substituent.	3.41	7	0	penicillanic acids
guaiane guaiane: from Artemisia caruifolia; structure in first source	2.11	1	0	sesquiterpene; terpenoid fundamental parent
oleanane oleanane: from the aerial roots of Ficus microcarpa; structure in first source	2.58	2	0	terpenoid fundamental parent; triterpene
taxane taxane: produced by Taxomyces andreanae	3.32	6	0	diterpene; terpenoid fundamental parent
ursane ursane: structure in first source	2.15	1	0	terpenoid fundamental parent; triterpene
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.	2.01	1	0
aldicarb Aldicarb: Carbamate derivative used as an insecticide, acaricide, and nematocide.. aldicarb : The oxime carbamate resulting from the addition of 2-methyl-2-(methylsulfanyl)propanaldoxime to methyl isocyanate. A member of the class of oxime carbamate insecticides, aldicarb is a mixture of E and Z isomers; it is not known which isomer is more active.	2.05	1	0
fenpyroximate fenpyroximate: structure in first source	2.75	3	0	pyrazole acaricide; tert-butyl ester	mitochondrial NADH:ubiquinone reductase inhibitor
2-hexyl-1-cyclopentanone thiosemicarbazone 2-hexyl-1-cyclopentanone thiosemicarbazone: inhibits HDL receptor SR-B1; structure in first source	5.25	18	0
disilver oxide [no description available]	2.08	1	0
cgp 56999a CGP 56999A: structure given in first source	2.03	1	0
4-(4-fluorophenoxy)benzaldehyde semicarbazone 4-(4-fluorophenoxy)benzaldehyde semicarbazone: structure in first source	3.13	1	0
ucb 34714 brivaracetam: A pyrrolidinone compound that is used to treat partial onset seizures in adult patients; structure in first source.. brivaracetam : A non-proteinogenic amino acid derivative that is butanamide in which the pro-S hydrogen at position 2 is replaced by a (4R)-2-oxo-4-propylpyrrolidin-1-yl. Used for treatment of partial onset seizures related to epilepsy.	3.31	1	0	gamma-lactam; non-proteinogenic amino acid derivative	anticonvulsant
pd 150606 PD 150606: a calpain inhibitor; structure given in first source. (Z)-3-(4-iodophenyl)-2-mercaptoacrylic acid : An organoiodine compound that is acrylic acid in which the vinylic hydrogens at positions 2 and 3 are replaced by mercapto and 4-iodophenyl groups respectively (the Z geoisomer).	2.25	1	0	cinnamic acids; organoiodine compound; thioenol	apoptosis inhibitor; calpain inhibitor
gambogic acid gambogic acid: RN given refers to (1R-(1alpha,1(Z),3abeta,5alpha,11beta,14aS*))-isomer	2.1	1	0	pyranoxanthones	metabolite
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.	1.99	1	0	organic molecular entity
flag peptide FLAG peptide: engineered as a tag for immunoaffinity purification of genetically-engineered proteins; amino acid sequence given in first source; a polar octapeptide. FLAG peptide : An eight amino acid peptide consisting of L-aspartic acid, L-tyrosine, L-lysine, four L-aspartic acid residues, and L-lysine joined in sequence by peptide linkages. It is widely used as a fusion tag for the purification and detection of a wide variety of recombinant proteins.	1.99	1	0	peptide
tetraborate tetraborate: RN given refers to ion(2-). borate ion : Any inorganic anion that is formally derived from boric acid. The term includes polymeric anions containing chains of BO3 structural units sharing one oxygen atom (e.g. di-, tri-, and tetraborates) as well as chains or rings sharing two oxygen atoms (e.g. metaborates).	2.05	1	0
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).	5.11	41	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
carbobenzoxy-leucyl-leucyl-norvalinal carbobenzoxy-leucyl-leucyl-norvalinal: structure given in first source	1.99	1	0	peptide
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).	10.22	3	1	dodecanoate ester; lipid A; tetradecanoate ester	Escherichia coli metabolite
sch 60663 SCH 60663: structure in first source	2.98	1	0
ginsenoside rb1 [no description available]	2.43	2	0	ginsenoside; glycoside; tetracyclic triterpenoid	anti-inflammatory drug; anti-obesity agent; apoptosis inhibitor; neuroprotective agent; plant metabolite; radical scavenger
2-((aminocarbonyl)amino)-5-(4-fluorophenyl)-3-thiophenecarboxamide 2-((aminocarbonyl)amino)-5-(4-fluorophenyl)-3-thiophenecarboxamide: an IKK-2 kinase inhibitor; structure in first source	2.53	2	0	aromatic amide; thiophenes
6''-o-malonyldaidzin 6''-O-malonyldaidzin: structure in first source. malonyldaidzin : A glycosyloxyisoflavone that is daidzein substituted by a 6-O-(carboxyacetyl)-beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage.	2.13	1	0	glycosyloxyisoflavone; hydroxyisoflavone; malonate ester; monosaccharide derivative	plant metabolite
thiocolchicoside thiocolchicoside: used in combination with glafenine and meprobamate to tranquilize patients undergoing hysterosalpingography; structure	4.9	1	1	glycoside
perampanel perampanel : A member of the class of bipyridines that is 2,3'-bipyridin-6'-one substituted at positions 1' and 5' by phenyl and 2-cyanophenyl groups respectively. Used as an adjunctive therapy for the treatment of partial-onset seizures in patients with epilepsy.	3.31	1	0	bipyridines; nitrile; pyridone	AMPA receptor antagonist; anticonvulsant
tocotrienols tocotrienol : A tocol in which the hydrocarbon chain at position 2 contains three double bonds.	2.54	2	0	diterpenoid
rucaparib AG14447: Poly(ADP-ribose) polymerase inhibitor; structure in first source	4.9	1	1	azepinoindole; caprolactams; organofluorine compound; secondary amino compound	antineoplastic agent; EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor
l 706000 L 706000: a spirobenzopyran piperidine; structure given in first source	2.06	1	0
medrogestone Medrogestone: 6,17-Dimethylpregna-4,6-diene-3,20-dione. A synthetic progestational hormone with actions similar to those of progesterone. It is used in the treatment of menstrual irregularities and has also been employed in the treatment of prostatic hypertrophy and endometrial carcinoma.	1.95	1	0	corticosteroid hormone
tetramethylrhodamine tetramethylrhodamine: RN given refers to perchlorate; structure	1.99	1	0	xanthene dye
u 18666a 3-beta-(2-(diethylamino)ethoxy)androst-5-en-17-one: inhibits cycloartenol synthase. 3beta-(2-diethylaminoethoxy)androst-5-en-17-one hydrochloride : A hydrochloride obtained by reaction of 3beta-(2-diethylaminoethoxy)androst-5-en-17-one with one equivalent of hydrochloric acid. It is a cholesterol synthesis and transport inhibitor.	1.99	1	0	hydrochloride	antiviral agent; EC 1.3.1.72 (Delta(24)-sterol reductase) inhibitor; Hedgehog signaling pathway inhibitor; nicotinic antagonist; sterol biosynthesis inhibitor
cgp 55845a CGP 55845A: GABA-B receptor antagonist; RN refers to cpd with no isomeric designation; CGP 55845 is the (1S,2S)-isomer	2.02	1	0
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.	1.98	1	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
hamigeran b hamigeran B: has antiviral activity; structure in first source	2.48	2	0
actein actein: a cyclolanostane from the Chinese drug Shoma; structure in first source	2.13	1	0	triterpenoid	metabolite
halichondrin b halichondrin B: from marine sponge Halichondria okadai; binds in the Vinca domain of tubulin	2.02	1	0	furopyran
delta-viniferin delta-viniferin: resveratrol dehydrodimer, an isomer of epsilon-viniferin; isolated from grapevine leaves; structure in first source. (2S,3S)-trans-delta-viniferin : A stilbenoid that is the (2S,3S)-trans-stereoisomer of delta-viniferin, obtained by cyclodimerisation of trans-resveratrol.	2.78	3	0	1-benzofurans; polyphenol; stilbenoid
ro3244794 RO3244794: structure in first source	2.05	1	0
artenimol artenimol: derivative of antimalarial drug artemisinin (quinghaosu)	4.9	1	1
alpha-synuclein alpha-Synuclein: A synuclein that is a major component of LEWY BODIES and plays a role in SYNUCLEINOPATHIES, neurodegeneration and neuroprotection.	2.8	3	0
tamiphosphor tamiphosphor: structure in first source	2.08	1	0
guanacastepene guanacastepene: isolated from an unidentified fungus; structure in first source	2.41	2	0
biapigenin biapigenin: bis-apigenin coupled at 3' & 3' positions; inhibits various cytochrome P450 enzymes; isolated from St. John's Wort	2.06	1	0	flavonoid oligomer
6-nonadecynoic acid 6-nonadecynoic acid: from the roots of Pentagonia gigantifolia; structure in first source	2.15	1	0
hirsutene hirsutene: structure in first source	2.43	2	0
indolapril hydrochloride Indolapril: structure given in first source	3.06	1	0
oxadiazoles Oxadiazoles: Compounds containing five-membered heteroaromatic rings containing two carbons, two nitrogens, and one oxygen atom which exist in various regioisomeric forms.	5.23	3	1
ly 341495 LY 341495: structure in first source	2.43	2	0
digalactosyldiacylglycerol digalactosyldiacylglycerol: two Galactoses bound to diacylglycerol; the mono Gal MGDG is also available; constitutes 20% of plant chloroplast lipids; see also 1,2-distearoyldigalactosyldiglyceride	3.92	3	0
d-ribo-phytosphingosine-1-phosphate phytosphingosine-1-phosphate: structure in first source. phytosphingosine 1-phosphate : A phosphosphingolipid that is phytosphingosine bearing a phospho group at position 1.	2.11	1	0	sphingoid 1-phosphate	Saccharomyces cerevisiae metabolite
theobroxide theobroxide: isolated from Lasiodiplodia theobromae; structure in first source	2.73	3	0
artemisic acid artemisic acid: isolated from Artemisia annua; MF: C28-H58-O; RN from Toxline. (+)-artemisinic acid : A monocarboxylic acid that is prop-2-enoic acid which is substituted at position 2 by a 4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl group (the 1S,4R,4aS,8aR diastereoisomer). It is a sesquiterpenoid precursor of artemisinin, obtained from sweet wormwood, Artemisia annua.	2.48	2	0	carbobicyclic compound; monocarboxylic acid; octahydronaphthalenes; sesquiterpenoid	metabolite
ucn 1028 c calphostin C: structure given in first source; isolated from Cladosporium cladosporioides	1.98	1	0
massadine massadine: a geranylgeranyltransferase type I inhibitor from the marine sponge Stylissa aff. massa.; structure in first source. massadine : An alkaloid isolated from Stylissa massa.	2.11	1	0	alkaloid; guanidines; organobromine compound; pyrrolecarboxamide	animal metabolite; EC 2.5.1.59 (protein geranylgeranyltransferase type I) inhibitor; marine metabolite
ribose ribopyranose : The pyranose form of ribose.	2.96	4	0	D-ribose; ribopyranose
pentalenene pentalenene: structure in first source	4.34	19	0	ortho-fused tricyclic hydrocarbon; sesquiterpene
dihydroartemisinic acid dihydroartemisinic acid: structure in first source. dihydroartemisinic acid : A monocarboxylic acid that is propanoic acid substituted at position 2 by a (1S,4R,4aS,8aR)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl group. It is a sesquiterpenoid precursor of the antimalarial drug, artemisinin.	2.48	2	0	carbobicyclic compound; monocarboxylic acid; octahydronaphthalenes; sesquiterpenoid	plant metabolite
lactulose Lactulose: A synthetic disaccharide used in the treatment of constipation and hepatic encephalopathy. It has also been used in the diagnosis of gastrointestinal disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p887). lactulose : A synthetic galactosylfructose disaccharide used in the treatment of constipation and hepatic encephalopathy.	4.9	1	1
calyciphylline b calyciphylline B: a hexacyclic alkaloid from Daphniphyllum calycinum; structure in first source	2.13	1	0
puraquinonic acid puraquinonic acid: structure in first source	2.41	1	0
arachidin-1 arachidin-1: structure in first source	2.59	2	0
3-cyano-n-(1,3-diphenyl-1h-pyrazol-5-yl)benzamide 3-cyano-N-(1,3-diphenyl-1H-pyrazol-5-yl)benzamide: affects mGluR5 receptors; structure in first source	2.06	1	0
lucidone lucidone: a compound with antiinflammatory activity from fruits of Lindera erythrocarpa; structure in first source	3.79	10	0	olefinic compound
fg-4592 roxadustat: structure in first source. roxadustat : An N-acylglycine resulting from the formal condensation of the amino group of glycine with the carboxy group of 4-hydroxy-1-methyl-7-phenoxyisoquinoline-3-carboxylic acid. It is an inhibitor of hypoxia inducible factor prolyl hydroxylase (HIF-PH).	2.25	1	0	aromatic ether; isoquinolines; N-acylglycine	EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor; EC 1.14.11.29 (hypoxia-inducible factor-proline dioxygenase) inhibitor
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.	4.17	5	0	nystatins
linoleic acid hydroperoxide linoleic acid hydroperoxide: RN refers to (Z,Z)-isomer. linoleic acid hydroperoxide : A HPODE that is a mono-hydroperoxy derivative of linoleic acid	2.03	1	0
arachidin-3 arachidin-3: an NSAID and antioxidant isolated from Arachis hypogaea; structure in first source	2.59	2	0
quinine lochnericine: from elicited cell cultures of Catharanthus roseus; structure in first source. lochnericine : An Aspidosperma alkaloid with molecular formula C21H24N2O3 found in the roots of Madagascar periwinkle (Catharanthus roseus, formerly known as Vinca rosea).	2.08	1	0	Aspidosperma alkaloid; epoxide; methyl ester; monoterpenoid indole alkaloid; organic heterohexacyclic compound	plant metabolite
nutlin-3a nutlin 3: an MDM2 antagonist; structure in first source	2.54	2	0	stilbenoid
tricycloclavulone tricycloclavulone: prostanoid-related marine oxylipin, isolated from the Okinawan soft coral Clavularia viridis; structure in first source	2.02	1	0
nvp-aew541 [no description available]	2.1	1	0
32,33,34,35-bacteriohopanetetrol 32,33,34,35-bacteriohopanetetrol: hopanoid from Rhodopseudomonas acidophila; structure given in first source. bacteriohopane-32,33,34,35-tetrol : A hopanoid that is bacteriohopane carrying four hydroxy substituents at positions 32, 33, 34 and 35.	2.02	1	0	hopanoid; tetrol	antimicrobial agent; bacterial metabolite; lipoxygenase inhibitor
tavaborole tavaborole: has antifungal activity; structure in first source. tavaborole : A member of the class of benzoxaboroles that is 1,3-dihydro-1-hydroxy-2,1-benzoxaborole substituted at position 5 by a fluoro group. A topical antifungal agent used for the treatment of onychomycosis (fungal infection of the toenails and fingernails).	3.21	1	0	benzoxaborole; organofluorine compound	antifungal agent; EC 6.1.1.4 (leucine--tRNA ligase) inhibitor; protein synthesis inhibitor
olodaterol [no description available]	3.21	1	0	aromatic ether; benzoxazine; phenols; secondary alcohol; secondary amino compound	beta-adrenergic agonist; bronchodilator agent
pyrazolone pyrazolone: non-steroid antirheumatic agent. pyrazolone : A member of the class of pyrazoles in which one of the carbons of the pyrazole ring is substituted by an oxo group.	2.81	3	0
vabicaserin vabicaserin: an antipsychotic agent and 5-HT2C receptor agonist; structure in first source	2.11	1	0
ibodutant 6-methylbenzo(b)thiophene-2-carboxylic acid (1-(2-phenyl-((1-(tetrahydropyran-4-ylmethyl)piperidin-4-ylmethyl)carbamoyl)ethylcarbamoyl)cyclophenyl)amide: a tachykinin NK2 receptor antagonist; structure in first source	2.03	1	0
jiadifenin jiadifenin: seco-prezizaane-type sesquiterpene with neurotrophic activity from Illicium jiadifengpi; structure in first source	3.51	1	0
carfilzomib [no description available]	2.63	2	0	epoxide; morpholines; tetrapeptide	antineoplastic agent; proteasome inhibitor
cortistatin a cortistatin A: structure in first source. cortistatin A : A member of the class of cortistatins that is substituted by hydroxy groups at positions 1 and 2, a dimethylamino group at the 3alpha position and an isoquinolin-7-yl group at the 17 position, with double bonds at the 9-11 and 10-19 positions (the 1R,2R,17beta enantiomer).	2.05	1	0	cortistatins; diol; secondary alcohol
n-dodecanoyl-dl-homoserine lactone N-dodecanoyl-DL-homoserine lactone: structure in first source	2.5	2	0	N-acyl-amino acid
chlorophyll b [no description available]	2.83	3	0	chlorophyll	cofactor
veratridine Veratridine: A benzoate-cevane found in VERATRUM and Schoenocaulon. It activates SODIUM CHANNELS to stay open longer than normal.	2.72	3	0
nepetalactol nepetalactol: a sex pheromone isolated from the potato aphid, Macrosiphum euphorbiae; structure in first source. cis-trans-nepetalactol : A cyclopentapyran that is 1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran substituted at position 1 by a hydroxy group and at positions 4 and 7 by methyl groups (the 4aS,7S,7aR-diastereomer)	3.29	6	0	cyclopentapyran; lactol
n,n'-dibenzhydrylethane-1,2-diamine dihydrochloride N,N'-dibenzhydrylethane-1,2-diamine dihydrochloride: selective metabotropic glutamate receptor 7 agonist; structure in first source. AMN082 dihydrochloride : A hydrochloride obtained by combining N,N'-bis(diphenylmethyl)ethane-1,2-diamine with two molar equivalent of hydrochloric acid.	2.13	1	0	hydrochloride	geroprotector; metabotropic glutamate receptor agonist; neuroprotective agent
phytic acid inositol pentaphosphate: RN given refers to cpd without isomeric designation	3.85	3	0	inositol phosphate
scopadulcic acid b scopadulcic acid B: isolated from Scorparia dulcis	2.02	1	0
alpha-conhydrine alpha-conhydrine: structure in first source	2.05	1	0
vinyl triflate vinyl triflate: structure in first source	2.01	1	0
streptazolin streptazolin: from culture of Streptomyces sp.; structure in first source	2.43	2	0
n-acetylmannosamine N-acetylmannosamine: RN given refers to cpd without isomeric designation. N-acetylmannosamine : Any mannosamine carrying an N-acetyl substituent	1.97	1	0
peramivir peramivir hydrate : A hydrate that is the trihydrate form of peramivir. Used for the treatment of acute uncomplicated influenza in patients 18 years and older who have been symptomatic for no more than two days.. peramivir : A member of the class of guanidines that is used (as its trihydrate) for the treatment of acute uncomplicated influenza in patients 18 years and older who have been symptomatic for no more than two days.	17.34	251	23
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.	4.19	17	0	benzoxazole
dextrothyroxine [no description available]	2.44	2	0
sepharose agarose : A linear polysaccharide made up from alternating D-galactose and 3,6-anhydro-alpha-L-galactopyranose residues joined by alpha-(1->3)- and beta-(1->4)-linkages.	2.08	1	0
indocyanine green Indocyanine Green: A tricarbocyanine dye that is used diagnostically in liver function tests and to determine blood volume and cardiac output.	1.95	1	0	1,1-diunsubstituted alkanesulfonate; benzoindole; cyanine dye
scopolamine hydrobromide [no description available]	6.72	18	1
vindoline [no description available]	3.14	5	0
pituitrin Pituitrin: A substance or extract from the neurohypophysis (PITUITARY GLAND, POSTERIOR).	4.59	10	0
hexahydroindolinone hexahydroindolinone: structure in first source	2.06	1	0
chaulmoogric acid chaulmoogric acid: component of CHAULMOOGRA OIL; RN given refers to parent cpd; structure. (R)-chaulmoogric acid : The (R)-enantiomer of chaulmoogric acid.. chaulmoogric acid : A monounsaturated long-chain fatty acid composed of tridecanoic acid having a 2-cyclopentenyl substituent at the 13-position.	2.65	3	0	chaulmoogric acid
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.	4.4	19	0
oplodiol oplodiol: RN given for (1S-(1alpha,4alpha,4aalpha,8abeta))-isomer. oplodiol : A carbobicyclic compound that is 1,2,3,4,4a,5,8,8a-octahydronaphthalene which is substituted by hydroxy groups at positions 1 and 4, an isoopropyl group at position 7, and by methyl groups at positions 1 and 4a (the 1S,4R,4aR,8aR isomer). A sesquiterpenoid plant metabolite.	2.03	1	0	carbobicyclic compound; octahydronaphthalenes; secondary alcohol; sesquiterpenoid; tertiary alcohol	plant metabolite
noratropine noratropine: RN given refers to endo-(+-)-isomer	2.07	1	0
titanocene titanocene: C10-H10-Ti. titanocene : A bis(eta(5)-cyclopentadienyl)metal(II) having Ti(II) as the metal(II) species. The parent of the class of titanonocenes.	3.83	3	0
clove Madagascar: One of the Indian Ocean Islands off the southeast coast of Africa. Its capital is Antananarivo. It was formerly called the Malagasy Republic. Discovered by the Portuguese in 1500, its history has been tied predominantly to the French, becoming a French protectorate in 1882, a French colony in 1896, and a territory within the French union in 1946. The Malagasy Republic was established in the French Community in 1958 but it achieved independence in 1960. Its name was changed to Madagascar in 1975. (From Webster's New Geographical Dictionary, 1988, p714)	2.48	2	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.	3.38	7	0
ants Ants: Insects of the family Formicidae, very common and widespread, probably the most successful of all the insect groups. All ants are social insects, and most colonies contain three castes, queens, males, and workers. Their habits are often very elaborate and a great many studies have been made of ant behavior. Ants produce a number of secretions that function in offense, defense, and communication. (From Borror, et al., An Introduction to the Study of Insects, 4th ed, p676)	3.48	8	0
bisdesmoside bisdesmoside: cytotoxic saponin from tubers of Bolbostemma paniculatum; structure in first source	2.21	1	0
alisol b monoacetate alisol B 23-acetate: from Alisma orientale rhizome; structure in first source	2.21	1	0	triterpenoid
isolongifolenone isolongifolenone: natural compound found in the Tauroniro tree (Humiria balsamifera) of South America, Insecticide for mosquito control	2.07	1	0
butaprost butaprost: highly selective prostaglandin receptor agonist; structure given in first source	2	1	0
peonidin 3-glucoside peonidin 3-glucoside: the methylated form of cyanidin 3-glucoside	2.01	1	0
2-aminoindan-2-phosphonic acid 2-aminoindan-2-phosphonic acid: inhibits salicylic acid synthesis	2.97	4	0
methampicillin brassinazole: a triazole-type brassinosteroid biosynthesis inhibitor; structure in first source. brassinazole : A member of the class of triazoles that is butan-2-ol which is substituted at positions 2, 3, and 4 by phenyl, 1H-1,2,4-triazol-1-yl and p-chlorophenyl groups, respectively. An inhibitor of brassinosteroid biosynthesis.	2.06	1	0	monochlorobenzenes; tertiary alcohol; triazoles	brassinosteroid biosynthesis inhibitor
friedelane friedelane: from leaves of Maytenus aquifolium (Celastraceae); structure in first source. friedelane : A triterpene that is docosahydropicene substituted by 8 methyl groups at positions 2, 2, 4a, 6a, 8a, 9, 12b and 14a.	2.21	1	0	triterpene	metabolite
cyanidin-3-o-beta-glucopyranoside cyanidin-3-O-beta-glucopyranoside: a natural compound distributed in several fruits & vegetables, such as strawberry, rhubarb, cherry, red cabbage, red onion, cranberries, etc.	2.78	3	0
malonylgenistin malonylgenistin: structure in first source. malonylgenistin : A glycosyloxyisoflavone that is genistin in which the hydroxy hydrogen at position 6'' has been replaced by a malonyl group.	2.13	1	0	beta-D-glucoside; glycosyloxyisoflavone; hydroxyisoflavone; malonate ester; monosaccharide derivative	plant metabolite
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	6.82	20	1	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
cytochrome c-t Cytochromes c: Cytochromes of the c type that are found in eukaryotic MITOCHONDRIA. They serve as redox intermediates that accept electrons from MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX III and transfer them to MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX IV.	3.77	10	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.	2.36	2	0
atrial natriuretic factor Atrial Natriuretic Factor: A potent natriuretic and vasodilatory peptide or mixture of different-sized low molecular weight PEPTIDES derived from a common precursor and secreted mainly by the HEART ATRIUM. All these peptides share a sequence of about 20 AMINO ACIDS.	2.69	3	0	polypeptide
hevein hevein: 43-amino acid residue protein from the rubber tree; homology with thionins and WHEAT GERM AGGLUTININS; not strictly a lectin since it does not act as an agglutinin but has the hevein motif characteristic of lectins;	2	1	0
nociceptin [no description available]	1.99	1	0	organic molecular entity; polypeptide	human metabolite; rat metabolite
alamethicin Alamethicin: A cyclic nonadecapeptide antibiotic that can act as an ionophore and is produced by strains of Trichoderma viride. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)	3.29	6	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.	2.68	3	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.	2.03	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.	4.16	5	0	peptide hormone
big gastrin big gastrin: isolated from Zollinger-Ellison syndrome gastrinomas & hog antral mucosa; have encountered tetratricontapeptide & nonadecapeptide gastrin; big-big gastrin significantly higher in patients with duodenal ulcers; big gastrin refers gastrin which has a longer peptide chain than the normal heptadecapeptide gastrin	2.68	3	0
iberiotoxin [no description available]	2.03	1	0
tannins Tannins: Polyphenolic compounds with molecular weights of around 500-3000 daltons and containing enough hydroxyl groups (1-2 per 100 MW) for effective cross linking of other compounds (ASTRINGENTS). The two main types are HYDROLYZABLE TANNINS and CONDENSED TANNINS. Historically, the term has applied to many compounds and plant extracts able to render skin COLLAGEN impervious to degradation. The word tannin derives from the Celtic word for OAK TREE which was used for leather processing.	3.26	5	0
oligonucleotides [no description available]	4.03	14	0
glucagon-like peptide 1 Glucagon-Like Peptide 1: A peptide of 36 or 37 amino acids that is derived from PROGLUCAGON and mainly produced by the INTESTINAL L CELLS. GLP-1(1-37 or 1-36) is further N-terminally truncated resulting in GLP-1(7-37) or GLP-1-(7-36) which can be amidated. These GLP-1 peptides are known to enhance glucose-dependent INSULIN release, suppress GLUCAGON release and gastric emptying, lower BLOOD GLUCOSE, and reduce food intake.	2.17	1	0
cellulose DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.	6.65	15	1	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)	2.52	2	0
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	4.46	23	0	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.	3.37	7	0	N-acylsphingosine	fluorescent probe
mk-8776 MK-8776: a checkpoint kinase 1 (CHK1) inhibitor; SCH900776 was renamed MK-8776; structure in first source	2.17	1	0	pyrazolopyrimidine
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.	5.91	90	0	chlorophyll; methyl ester	cofactor
3-(3-(4-((pyridin-2-yloxy)methyl)benzyl)isoxazol-5-yl)pyridin-2-amine APX001A: has antifungal activity; structure in first source	4.9	1	1
pevonedistat pevonedistat: a potent and selective inhibitor of NAE (NEDD8-activating enzyme). pevonedistat : A pyrrolopyrimidine that is 7H-pyrrolo[2,3-d]pyrimidine which is substituted by a (1S)-2,3-dihydro-1H-inden-1-ylnitrilo group at position 4 and by a (1S,3S,4S)-3-hydroxy-4-[(sulfamoyloxy)methyl]cyclopentyl group at position 7. It is a potent and selective NEDD8-activating enzyme inhibitor with an IC50 of 4.7 nM, and currently under clinical investigation for the treatment of acute myeloid leukemia (AML) and myelodysplastic syndromes.	17.15	270	11	cyclopentanols; indanes; pyrrolopyrimidine; secondary amino compound; sulfamidate	antineoplastic agent; apoptosis inducer
jsh 23 4-methyl-N1-(3-phenylpropyl)benzene-1,2-diamine: structure in first source. JSH-23 : A diamine that is 1,2-phenylenediamine carrying a methyl substituent at position 4 and a 3-phenylpropyl substituent at position N1.	2.13	1	0	diamine; substituted aniline	NF-kappaB inhibitor
sphingosine kinase [no description available]	2.15	1	0
ubiquinone Ubiquinone: A lipid-soluble benzoquinone which is involved in ELECTRON TRANSPORT in mitochondrial preparations. The compound occurs in the majority of aerobic organisms, from bacteria to higher plants and animals.	4.9	1	1
calpain Calpain: Cysteine proteinase found in many tissues. Hydrolyzes a variety of endogenous proteins including NEUROPEPTIDES; CYTOSKELETAL PROTEINS; proteins from SMOOTH MUSCLE; CARDIAC MUSCLE; liver; platelets; and erythrocytes. Two subclasses having high and low calcium sensitivity are known. Removes Z-discs and M-lines from myofibrils. Activates phosphorylase kinase and cyclic nucleotide-independent protein kinase. This enzyme was formerly listed as EC 3.4.22.4.	2.25	1	0
lucifer yellow lucifer yellow: RN given refers to di-Li salt	2.68	3	0	organic lithium salt	fluorochrome
miltiradiene miltiradiene: from Saccharomyces cerevisiae; structure in first source. miltiradiene : An abietadiene in which the two doule bonds are located at positions 8 and 12. It is a key intermediate in the biosynthesis of many important natural diterpene compounds such as triptolide, tanshinones, carnosic acid and carnosol.	2.11	1	0	abietadiene; carbotricyclic compound	plant metabolite
9-hydroxy-12-oxo-10(e)-dodecenoic acid 9-hydroxy-12-oxo-10(E)-dodecenoic acid: structure given in first source	2	1	0
sapogenins Sapogenins: The aglucon moiety of a saponin molecule. It may be triterpenoid or steroid, usually spirostan, in nature.	3.16	5	0
hydroxyoctadecadienoic acid hydroxyoctadecadienoic acid: structure in first source	2.07	1	0
strictamine strictamine: structure	2.15	1	0
3-hydroxycyclopent-1-enecarboxylic acid 3-hydroxycyclopent-1-enecarboxylic acid: binds gamma-hydroxybutyrate receptors; structure in first source	3.39	6	0
chitosan [no description available]	5.02	36	0
volicitin volicitin: an elicitor that triggers emission of volatile from plants	5.13	8	0
dihydroazulene dihydroazulene: structure in first source	2.46	2	0
perylenequinone perylenequinone: structure in first source	3.16	1	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	1	0
9-(tetrahydro-2-furyl)-adenine [no description available]	2	1	0
15-deoxyprostaglandin j2 15-deoxyprostaglandin J2: 15d-PGJ2 abbreviation is also used for 15-deoxy-delta(12,14)PGJ2	4.07	14	0
1-palmitoyl-2-(5-oxovaleroyl)-sn-glycero-3-phosphorylcholine 1-O-palmitoyl-2-O-(5-oxovaleryl)-sn-glycero-3-phosphocholine : A 1,2-diacyl-sn-glycero-3-phosphocholine having palmitoyl and 5-oxovaleryl groups at the 1- and 2-positions respectively; major species at pH 7.3.	2.11	1	0	1,2-diacyl-sn-glycero-3-phosphocholine; aldehyde	apoptosis inducer
sodium oxybate Sodium Oxybate: The sodium salt of 4-hydroxybutyric acid. It is used for both induction and maintenance of ANESTHESIA.	2.58	2	0
bucladesine Bucladesine: A cyclic nucleotide derivative that mimics the action of endogenous CYCLIC AMP and is capable of permeating the cell membrane. It has vasodilator properties and is used as a cardiac stimulant. (From Merck Index, 11th ed). bucladesine : A 3',5'-cyclic purine nucleotide that is the 2'-butanoate ester and 6-N-butanoyl derivative of 3',5'-cyclic AMP.	2.92	4	0	3',5'-cyclic purine nucleotide
sodium hypochlorite Sodium Hypochlorite: It is used as an oxidizing and bleaching agent and as a disinfectant. (From Grant & Hackh's Chemical Dictionary, 5th ed). sodium hypochlorite : An inorganic sodium salt in which hypochlorite is the counterion. It is used as a bleaching and disinfecting agent and is commonly found in household bleach.	1.94	1	0	inorganic sodium salt	bleaching agent; disinfectant
4-hydroxymercuribenzoate [no description available]	1.94	1	0
stearates Stearates: Salts and esters of the 18-carbon saturated, monocarboxylic acid--stearic acid.	3.51	2	0
arginine Teniposide: A semisynthetic derivative of PODOPHYLLOTOXIN that exhibits antitumor activity. Teniposide inhibits DNA synthesis by forming a complex with topoisomerase II and DNA. This complex induces breaks in double stranded DNA and prevents repair by topoisomerase II binding. Accumulated breaks in DNA prevent cells from entering into the mitotic phase of the cell cycle, and lead to cell death. Teniposide acts primarily in the G2 and S phases of the cycle.. teniposide : A furonaphthodioxole that is a synthetic derivative of podophyllotoxin with anti-tumour activity; causes single- and double-stranded breaks in DNA and DNA-protein cross-links and prevents repair by topoisomerase II binding.	1.99	1	0
borrelidin treponemycin: isolated from Streptomyces albovinaceous; active against Treponema hyodysenteriae. borrelidin : A macrolide that is isolated from several Streptomyces species and displays antibiotic, antineoplastic and antimalarial properties.	2.67	3	0	aliphatic nitrile; diol; macrolide; monocarboxylic acid; secondary alcohol	antifungal agent; antimalarial; antimicrobial agent; antineoplastic agent; apoptosis inducer; bacterial metabolite
epi-isozizaene epi-isozizaene: structure in first source	2.25	1	0	sesquiterpene
olaparib [no description available]	2.15	1	0	cyclopropanes; monofluorobenzenes; N-acylpiperazine; phthalazines	antineoplastic agent; apoptosis inducer; EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor
picrotoxinin picrotoxinin: toxic component of PICROTOXIN; structure; noncompetitive antagonist of ionotropic GABA-A receptors. picrotoxinin : A picrotoxane sesquiterpenoid that is 3a,4,5,6,7,7a-hexahydro-1H-indene-3,7-dicarboxylic acid which is substituted at positions 3a, 6, and 7a by methyl, isopropenyl, and hydroxy groups, respectively; in which the double bond at position 2-3 has been epoxidised; and in which the carboxy groups at positions 3 and 7 have undergone gamma-lactone formation by O-alkylation to positions 4 and 5, respectively. A component of picrotoxin.	2.75	3	0
tuberonic acid glucoside tuberonic acid glucoside: isolated from the potato Solanum tuberosum; structure in first source	3.54	8	0	O-acyl carbohydrate
arenaemycin e arenaemycin E: from Streptomyces species; arenaemycin C is the chlorhydrin of the parent cpd, arenaemycin D is the diol & arenaemycin E is the epoxide; structure. pentalenolactone : A sesquiterpene lactone that is isolated from several Streptomyces species and exhibits antibiotic activity.	1.95	1	0	alpha,beta-unsaturated monocarboxylic acid; organic heterotricyclic compound; sesquiterpene lactone; spiro-epoxide	antimicrobial agent; bacterial metabolite; EC 1.2.1.12 [glyceraldehyde-3-phosphate dehydrogenase (phosphorylating)] inhibitor
methyl jasmonate [no description available]	15.72	1,686	1
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.	3.04	5	0	organic cation; sulfonium compound	coenzyme; cofactor; human metabolite; micronutrient; Mycoplasma genitalium metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
mln 8237 MLN 8237: an aurora kinase A inhibitor	2.1	1	0	benzazepine
picrotoxin Picrotoxin: A noncompetitive antagonist at GABA-A receptors and thus a convulsant. Picrotoxin blocks the GAMMA-AMINOBUTYRIC ACID-activated chloride ionophore. Although it is most often used as a research tool, it has been used as a CNS stimulant and an antidote in poisoning by CNS depressants, especially the barbiturates.. picrotoxin : A mixture consisting of equimolar amounts of picrotoxinin and picrotin found in the climbing plant Anamirta cocculus.	3.86	12	0
madecassoside [no description available]	2.47	2	0	carboxylic ester; pentacyclic triterpenoid; trisaccharide derivative; triterpenoid saponin	anti-inflammatory agent; antioxidant; antirheumatic drug; plant metabolite; vulnerary
10-nitro-oleic acid 10-nitro-oleic acid: structure in first source. (9E)-10-nitrooctadecenoic acid : A nitro fatty acid that is (9E)-octadec-9-enoic (elaidic) acid substituted by a nitro group at position 10.	2.06	1	0	long-chain fatty acid; monounsaturated fatty acid; nitro fatty acid	human metabolite
insulin, isophane Insulin, Isophane: An intermediate-acting INSULIN preparation with onset time of 2 hours and duration of 24 hours. It is produced by crystallizing ZINC-insulin-PROTAMINES at neutral pH 7. Thus it is called neutral protamine Hagedorn for inventor Hans Christian Hagedorn.	1.94	1	0
arabinogalactan [no description available]	2.44	2	0
colletoic acid colletoic acid: an 11beta-hydroxysteroid dehydrogenase type 1 inhibitor from Colletotrichum gloeosporioides; structure in first source	2.04	1	0
sch772984 [no description available]	2.25	1	0	biaryl; indazoles; N-acylpiperazine; N-alkylpyrrolidine; N-arylpiperazine; pyridines; pyrimidines; pyrrolidinecarboxamide; secondary carboxamide; tertiary amino compound; tertiary carboxamide	analgesic; antineoplastic agent; apoptosis inducer; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor
mk 2206 MK 2206: a protein kinase inhibitor and antineoplastic agent	2.17	1	0	organic heterotricyclic compound	EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor
vu0357017 [no description available]	2.21	1	0
4,4-difluoro-4-bora-3a,4a-diaza-s-indacene [no description available]	2.92	4	0	BODIPY compound
quetiapine fumarate Quetiapine Fumarate: A dibenzothiazepine and ANTIPSYCHOTIC AGENT that targets the SEROTONIN 5-HT2 RECEPTOR; HISTAMINE H1 RECEPTOR, adrenergic alpha1 and alpha2 receptors, as well as the DOPAMINE D1 RECEPTOR and DOPAMINE D2 RECEPTOR. It is used in the treatment of SCHIZOPHRENIA; BIPOLAR DISORDER and DEPRESSIVE DISORDER.	3.27	1	0	fumarate salt
cardiovascular agents Cardiovascular Agents: Agents that affect the rate or intensity of cardiac contraction, blood vessel diameter, or blood volume.	5.04	10	1
systemin systemin: amino acid sequence given in first source; a mobile 18 amino acid polypeptide, induces proteinase inhibitor synthesis; from Lycopersicon esculentum (tomato)	7.93	31	0
albaflavenone albaflavenone: an alpha,beta-unsaturated sesquiterpene ketone with a zizaene skeleton; produced by a streptomycete; structure given in first source. albaflavenone : A carbotricyclic compound that is (+)-epi-isozizaene in which the hydrogens at position 5 have been replaced by an oxo group.	2.1	1	0	carbocyclic antibiotic; carbotricyclic compound; cyclic terpene ketone; enone; sesquiterpenoid	bacterial metabolite
mannans [no description available]	5.19	3	1
glasdegib glasdegib: a smoothened inhibitor. glasdegib : A member of the class of benzimidazoles that is 1H-benzimidazole which is substituted by a (2R,4S)-4-{[(4-cyanophenyl)carbamoyl]amino}-1-methylpiperidin-2-yl group at position 2. It is a hedgehog signalling pathway inhibitor that acts by binding to Smoothened (SMO) receptors and blocking signal transduction (IC50 = 5 nM). It is used in combination with low-dose cytarabine, for the treatment of newly-diagnosed acute myeloid leukemia (AML) in adult patients (aged >= 75 years), or who have medical conditions that prevent the use of standard chemotherapy.	3.31	1	0	benzimidazoles; nitrile; phenylureas; piperidines	antineoplastic agent; Hedgehog signaling pathway inhibitor; SMO receptor antagonist
phosphinothricin phosphinothricin: RN given refers to parent cpd with unspecified isomeric designation; structure. phosphinothricin(1-) : Conjugate base of phosphinothricin arising from deprotonation of the phosphinate function.	2.21	1	0	organic anion
etheroleic acid etheroleic acid: a divinyl ether; structure given in first source. etheroleic acid : A divinyl ether fatty acid that is (9Z,11E,14E)-nonadeca-9,11,14-trienoic acid in which the methylene group at position 10 has been replaced by oxygen.	2.11	1	0	divinyl ether fatty acid; long-chain fatty acid
phytochromobilin phytochromobilin: structure given in first source; this bilin is a pigment derived from phycoerythrobilin-containing proteins. phytochromobilin : A member of the class of bilins which functions as the chromophore of light-sensing phytochromes in plants.. (3Z)-phytochromobilin(2-) : Dicarboxylate anion of (3Z)-phytochromobilin.	2.06	1	0
(5-(2,4-bis((3s)-3-methylmorpholin-4-yl)pyrido(2,3-d)pyrimidin-7-yl)-2-methoxyphenyl)methanol (5-(2,4-bis((3S)-3-methylmorpholin-4-yl)pyrido(2,3-d)pyrimidin-7-yl)-2-methoxyphenyl)methanol: a potent, selective, and orally bioavailable ATP-competitive mammalian target of rapamycin kinase inhibitor with in vitro and in vivo antitumor activity; structure in first source	2.58	2	0	benzyl alcohols; morpholines; pyridopyrimidine; tertiary amino compound	antineoplastic agent; apoptosis inducer; mTOR inhibitor
8-iso-prostaglandin a2 8-isoprostaglandin A2: a cyclopentenone isoprostane	2.94	4	0	prostanoid
ss220 SS220: Insect Repellent	2.45	2	0
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
1-(4-methoxybenzyl)-5-(trifluoromethoxy)indoline-2,3-dione [no description available]	2.21	1	0
urushiol [no description available]	1.98	1	0
glycolipids [no description available]	6.01	36	0
piperidines Piperidines: A family of hexahydropyridines.	6.71	44	0
resolvin d1 resolvin D1: an anti-inflammatory lipid mediator; structure in first source. resolvin D1 : A resolvin that is docosa-4Z,9E,11E,13Z,15E,19Z-hexaenoic acid which is substituted by hydroxy groups at the 7, 8, and 17 positions (the 7S,8R,17S-stereoisomer).	3.13	1	0	hydroxy polyunsaturated fatty acid; resolvin; triol	anti-inflammatory agent
cyanidin 3-galactoside cyanidin 3-galactoside: structure in first source	2.08	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.	3.67	9	0
4-hydroxymellein 4-hydroxymellein: alpha-Glucosidase Inhibitor from Xylaria feejeensis associated with Hintonia latiflora; structure in first source. 4-hydroxymellein : An isochromane that is mellein bearing a hydroxy group at position 4.	2.15	1	0
methyl 4,5-didehydrojasmonate methyl 4,5-didehydrojasmonate: structure in first source	2.74	3	0
sordarin sordarin: antifungal mold metabolite of Sordaria araneosa; sordarins A and B are stereoisomers. sordarin : An antifungal metabolite of Sordaria araneosa that inhibits protein synthesis. It has a tetracyclic diterpene glycoside structure.	2.05	1	0
11-nor-delta(9)-tetrahydrocannabinol-9-carboxylic acid 11-nor-delta(9)-tetrahydrocannabinol-9-carboxylic acid: RN given refers to cpd without isomeric designation; a major acidic metabolite of tetrahydrocannabinol in human urine	2.05	1	0	1-benzopyran
gilteritinib gilteritinib: an FLT3/AXL protein tyrosine kinase inhibitor. gilteritinib : A member of the class of pyrazines that is pyrazine-2-carboxamide which is substituted by {3-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}nitrilo, (oxan-4-yl)nitrilo and ethyl groups at positions 3,5 and 6, respectively. It is a potent inhibitor of FLT3 and AXL tyrosine kinase receptors (IC50 = 0.29 nM and 0.73 nM, respectively). Approved by the FDA for the treatment of acute myeloid leukemia in patients who have a FLT3 gene mutation.	3.64	1	1	aromatic amine; monomethoxybenzene; N-methylpiperazine; oxanes; piperidines; primary carboxamide; pyrazines; secondary amino compound	antineoplastic agent; apoptosis inducer; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor
abt-199 venetoclax: A BCL-2 inhibitor with antineoplastic activity that is used in the treatment of CHRONIC LYMPHOCYTIC LEUKEMIA associated with chromosome 17p deletion; structure in first source.. venetoclax : A member of the class of pyrrolopyridines that is a potent inhibitor of the antiapoptotic protein B-cell lymphoma 2. It is used for treamtment of chronic lymphocytic leukemia with 17p deletion.	5.61	4	1	aromatic ether; C-nitro compound; monochlorobenzenes; N-alkylpiperazine; N-arylpiperazine; N-sulfonylcarboxamide; oxanes; pyrrolopyridine	antineoplastic agent; apoptosis inducer; B-cell lymphoma 2 inhibitor
4-hydroxyindol-3-ylmethylglucosinolate 4-hydroxyindol-3-ylmethylglucosinolate: an indole glucosinolate; structure in first source. 4-hydroxyglucobrassicin(1-) : An indolylmethylglucosinolate that is the conjugate base of 4-hydroxyglucobrassicin.	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.	1.94	1	0
butyrolactone i butyrolactone I: selective inhibitor of cdk2 & cdc2 kinase; structure given in first source	3.03	4	0	butenolide
isoquercitrin [no description available]	2.45	2	0
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).	2.37	2	0
natriuretic peptide, brain Natriuretic Peptide, Brain: A PEPTIDE that is secreted by the BRAIN and the HEART ATRIA, stored mainly in cardiac ventricular MYOCARDIUM. It can cause NATRIURESIS; DIURESIS; VASODILATION; and inhibits secretion of RENIN and ALDOSTERONE. It improves heart function. It contains 32 AMINO ACIDS.	2.48	2	0	polypeptide
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.	2.4	2	0
chondroitin Chondroitin: A mucopolysaccharide constituent of chondrin. (Grant & Hackh's Chemical Dictionary, 5th ed)	1.98	1	0
heparitin sulfate Heparitin Sulfate: A heteropolysaccharide that is similar in structure to HEPARIN. It accumulates in individuals with MUCOPOLYSACCHARIDOSIS.	3.37	7	0
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	6.69	41	0	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening 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.	5.39	2	1
oxytetracycline, anhydrous Oxytetracycline: A TETRACYCLINE analog isolated from the actinomycete STREPTOMYCES RIMOSUS and used in a wide variety of clinical conditions.. oxytetracycline : A tetracycline used for treatment of infections caused by a variety of Gram positive and Gram negative microorganisms including Mycoplasma pneumoniae, Pasteurella pestis, Escherichia coli, Haemophilus influenzae (respiratory infections), and Diplococcus pneumoniae.	2.02	1	0
isoascorbic acid isoascorbic acid: food antioxidant; (L)-isomer is ascorbic acid; RN given refers to (D)-isomer; structure	2	1	0	ascorbic acid
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.	8.79	99	0	monohydroxybenzoate	plant metabolite
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.	5.83	18	0	benzenes; hydroxycoumarin; methyl ketone
tenuazonic acid Tenuazonic Acid: 3-Acetyl-5-sec-butyl-4-hydroxy-3-pyrrolin-2-one. A metabolite found in a strain of the fungus Alternaria tenuis Auct. which functions as an antibiotic with antiviral and antineoplastic properties, and may also act as a mycotoxin.. tenuazonic acid : A member of the class of pyrrolidin-2-ones that is 5-(butan-2-yl)pyrrolidine-2,4-dione carrying an additional acetyl group at position 3. A mycotoxin produced by various plant pathogenic fungi.	2.03	1	0
l 701324 L 701324: a glycine/NMDA receptor antagonist	2.5	2	0	quinolines
4-hydroxycoumarin 2-hydroxychromone: structure	2.07	1	0	hydroxycoumarin
teriflunomide [no description available]	4.9	1	1	(trifluoromethyl)benzenes; aromatic amide; enamide; enol; nitrile; secondary carboxamide	drug metabolite; EC 1.3.98.1 [dihydroorotate oxidase (fumarate)] inhibitor; hepatotoxic agent; non-steroidal anti-inflammatory drug; tyrosine kinase inhibitor
reutericyclin reutericyclin: a new tetramic acid related to tenuazonic acid found in sourdough produced by Lactobacillus reuteri LTH2584 exhibits antimicrobial activity	2.03	1	0
tetramic acid tetramic acid : A gamma-lactam that is 1,3-dihydro-2H-pyrrol-2-one in which the hydrogen at position 4 has been replaced by a hydroxy group. Despite its simple structure, it was not synthesised until 1972; earlier attempts were later shown to have resulted only in the formation of the isomer 5-imino-4,5-dihydrofuran-3-ol.	2.04	1	0
2'-hydroxy-5,9-dimethyl-2-allyl-6,7-benzomorphan SK&F 10047: pharmacologic action of cpd may depend on (L)- or (D)-isomerism; RN given refers to cpd without isomeric designation	2.9	4	0
betalains Betalains: Compounds derived from TYROSINE via betalamic acid, including BETAXANTHINS and BETACYANINS. They are found in the Caryophyllales order of PLANTS and some BASIDIOMYCETES.	2.01	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.	2.68	3	0
brevetoxin brevetoxin: from Ptychodiscus brevis	2.03	1	0
bismuth oxybromide bismuth oxybromide: bismuth oxybromide (BiOBr) nanoplate microspheres were used to remove NO in indoor air under visible light irradiation	4.9	1	1
transforming growth factor beta Transforming Growth Factor beta: A factor synthesized in a wide variety of tissues. It acts synergistically with TGF-alpha in inducing phenotypic transformation and can also act as a negative autocrine growth factor. TGF-beta has a potential role in embryonal development, cellular differentiation, hormone secretion, and immune function. TGF-beta is found mostly as homodimer forms of separate gene products TGF-beta1, TGF-beta2 or TGF-beta3. Heterodimers composed of TGF-beta1 and 2 (TGF-beta1.2) or of TGF-beta2 and 3 (TGF-beta2.3) have been isolated. The TGF-beta proteins are synthesized as precursor proteins.	2.42	2	0
phytoestrogens Phytoestrogens: Compounds derived from plants, primarily ISOFLAVONES that mimic or modulate endogenous estrogens, usually by binding to ESTROGEN RECEPTORS.	4.9	1	1
oxathiapiprolin oxathiapiprolin: fungicide, structure in first source. 1-(4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone : An N-acylpiperidine that is N-acetyl 4-(1,3-thiazol-2-yl)piperidine in which the thiazole ring is substituted at position 4 by a 5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl group and in which one of the hydrogens of the acetyl group is replaced by a 5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl group.. oxathiapiprolin : A racemate comprising equimolar amounts of (R)- and (S)-oxathiapiprolin.	2.25	1	0	1,3-thiazoles; isoxazoline; N-acylpiperidine; organofluorine compound; pyrazoles; tertiary carboxamide
okadaic acid Okadaic Acid: A specific inhibitor of phosphoserine/threonine protein phosphatase 1 and 2a. It is also a potent tumor promoter. It is produced by DINOFLAGELLATES and causes diarrhetic SHELLFISH POISONING.. okadaic acid : A polycyclic ether that is produced by several species of dinoflagellates, and is known to accumulate in both marine sponges and shellfish. A polyketide, polyether derivative of a C38 fatty acid, it is one of the primary causes of diarrhetic shellfish poisoning (DSP). It is a potent inhibitor of specific protein phosphatases and is known to have a variety of negative effects on cells.	5.35	18	0	ketal
pyrethrins [no description available]	3.03	4	0
lsp4-2022 LSP4-2022: structure in first source	2.13	1	0
palau'amine palau'amine: structure in first source	2.73	3	0
hippolachnin a hippolachnin A: from the South China Sea sponge Hippospongia lachne; structure in first source	2.11	1	0
cb-839 [no description available]	2.31	1	0
ivosidenib ivosidenib: an inhibitor of isocitrate dehydrogenase 1 (IDH1) for treatment of acute myeloid leukemia (AML). ivosidenib : A tertiary carboxamide resulting from the formal condensation of the carboxy group of (2S)-1-(4-cyanopyridin-2-yl)-5-oxopyrrolidine-2-carboxylic acid with the secondary amino group of (2S)-2-(2-chlorophenyl)-N-(3,3-difluorocyclobutyl)-2-[(5-fluoropyridin-3-yl)amino]acetamide. It is approved by the FDA for the treatment of acute myeloid leukemia (AML) in patients with an isocitrate dehydrogenase-1 (IDH1) mutation.	5.12	2	1	cyanopyridine; monochlorobenzenes; organofluorine compound; pyrrolidin-2-ones; secondary carboxamide; tertiary carboxamide	antineoplastic agent; EC 1.1.1.42 (isocitrate dehydrogenase) inhibitor
hirudin Hirudin: A 65-residue polypeptide from LEECHES.	4.9	1	1
glutaminase [no description available]	2.31	1	0
cyclin d1 Cyclin D1: Protein encoded by the bcl-1 gene which plays a critical role in regulating the cell cycle. Overexpression of cyclin D1 is the result of bcl-1 rearrangement, a t(11;14) translocation, and is implicated in various neoplasms.	3.31	6	0
contraceptives, postcoital Contraceptives, Postcoital: Contraceptive substances to be used after COITUS. These agents include high doses of estrogenic drugs; progesterone-receptor blockers; ANTIMETABOLITES; ALKALOIDS, and PROSTAGLANDINS.	1.94	1	0
ganoderic acid ganoderic acid: from the fruiting body of Ganoderma; structure in first source	3.08	4	0
lysophosphatidylethanolamine lysophosphatidylethanolamine : A glycerophosphoethanolamine resulting from partial hydrolysis of a phosphatidylethanolamine, which removes one of the fatty acid groups. The structure is depicted in the image where R(1) = acyl, R(2) = H or where R(1) = H, R(2) = acyl.	2.31	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.	2.89	4	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).	2.65	3	0
ellagitannin ellagitannin: structure; precoxin A/ praecoxin A is a purified ellagitannin. ellagitannin : A form of hydrolysable tannin produced from ellagic acid. Ellagitannins are glucosides which are readily hydrolysed by water to regenerate ellagic acid when the plants are eaten.	3.16	1	0
2-(2'-pyridyldithio)benzyldiazoacetate 2-(2'-pyridyldithio)benzyldiazoacetate: structure given in first source; isomeric probe	4.31	16	0
phthalocyanine phthalocyanine : A tetrapyrrole fundamental parent that consists of four isoindole-type units, with the connecting carbon atoms in the macrocycle replaced by nitrogen.	2.48	2	0	phthalocyanines; tetrapyrrole fundamental parent
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)).	2.9	4	0	alpha-N-acetylneuraminyl-(2->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1')-ceramide; sialodiosylceramide; sialotriaosylceramide	mouse metabolite
nitrophenols Nitrophenols: PHENOLS carrying nitro group substituents.	2.02	1	0
glucagon-like peptide 2 Glucagon-Like Peptide 2: A 33-amino acid peptide derived from the C-terminal of PROGLUCAGON and mainly produced by the INTESTINAL L CELLS. It stimulates intestinal mucosal growth and decreased apoptosis of ENTEROCYTES. GLP-2 enhances gastrointestinal function and plays an important role in nutrient homeostasis.	1.99	1	0
angiotensin i Angiotensin I: A decapeptide that is cleaved from precursor angiotensinogen by RENIN. Angiotensin I has limited biological activity. It is converted to angiotensin II, a potent vasoconstrictor, after the removal of two amino acids at the C-terminal by ANGIOTENSIN CONVERTING ENZYME.. angiotensin I : A ten amino acid peptide formed by renin cleavage of angiotensinogen. Angiotensin I has no direct biological function except that high levels can stimulate catecholamine production. It is metabolized to its biologically active byproduct angiotensin II, a potent vasoconstrictor, by angiotensin converting enzyme (ACE) through cleavage of the two terminal amino acids.. angiotensin I dizwitterion : A peptide zwitterion that is the dizwitterionic form of angiotensin I having both carboxy groups deprotonated and the aspartyl amino group and arginine side-chain protonated. It is the major species at pH 7.3.	2.68	3	0	angiotensin; peptide zwitterion	human metabolite; neurotransmitter agent
bacoside a bacoside A: from Bacopa monnieri; structure in first source	2.08	1	0	triterpenoid saponin
rabdosiin rabdosiin: isolated from the stem of Rabdosia Japonica; structure in first source	2.03	1	0
harpagide harpagide: from S. African plant Harpagophytum procumbens DC	2.17	1	0
diospyros Diospyros: A plant genus of the family EBENACEAE, order Ebenales, subclass Dilleniidae, class Magnoliopsida best known for the edible fruit and the antibacterial activity and compounds of the wood.	2.43	2	0
ginkgolide b [no description available]	8.42	39	3
ginkgolide c ginkgolide C: ginkolide; inactive to PAF receptor; structure given in first source	4.1	15	0
gibberellins [no description available]	10.68	163	0
aldrin Aldrin: A highly poisonous substance that was formerly used as an insecticide. The manufacture and use has been discontinued in the U.S. (From Merck Index, 11th ed). aldrin : An organochlorine compound resulting from the Diels-Alder reaction of hexachlorocyclopentadiene with norbornadiene. A proinsecticide (by epoxidation of the non-chlorinated double bond to give dieldrin), it was widely used as an insecticide before being banned in the 1970s as a persistent organic pollutant.	2.03	1	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.	2.65	3	0
cyclopenta(cd)pyrene 3,4-oxide cyclopenta(cd)pyrene 3,4-oxide: structure given in first source	2.36	2	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.	3.53	2	0
wilforgine wilforgine: isolated from Tripterygium wilfordii; structure in first source. wilforgine : A dihydroagarofuran sesquiterpenoid and pyridine alkaloid with formula C41H47NO19 originally isolated from the roots of Tripterygium wilfordii.	2.53	2	0	acetate ester; dihydroagarofuran sesquiterpenoid; furans; macrocyclic lactone; organic heteropentacyclic compound; pyridine alkaloid	plant metabolite
cyclosporine Cyclosporine: A cyclic undecapeptide from an extract of soil fungi. It is a powerful immunosupressant with a specific action on T-lymphocytes. It is used for the prophylaxis of graft rejection in organ and tissue transplantation. (From Martindale, The Extra Pharmacopoeia, 30th ed).	2.04	1	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.	3.86	12	0
ginkgolide j ginkgolide J: a naturally occurring ginkgolide from GINKGO	2.72	3	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.	3.09	5	0
protopanaxadiol protopanaxadiol: triterpenoid sapogenin of ginsenosides from leaves of Panax ginseng; has antineoplastic activity; acid hydrolysis results in panaxadiol. protopanaxadiol : A tetracyclic triterpenoid sapogenin (isolated from ginseng) that is dammarane which is substituted by hydroxy groups at the 3beta, 12beta and 20 positions and in which a double bond has been introduced at the 24-25 position.	2.06	1	0
tomatine Tomatine: An alkaloid that occurs in the extract of leaves of wild tomato plants. It has been found to inhibit the growth of various fungi and bacteria. It is used as a precipitating agent for steroids. (From The Merck Index, 11th ed). tomatine : A steroid alkaloid that is tomatidine in which the hydroxy group at position 3 is linked to lycotetraose, a tetrasaccharide composed of two units of D-glucose, one unit of D-xylose, and one unit of D-galactose.	2.25	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.	1.99	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.	3.25	6	0
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	2.45	2	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.	3.37	7	0
angiogenin angiogenin: human tumor protein which stimulates growth of blood vessels; contains 123 amino acids; member of the pancreatic ribonuclease superfamily; MW 14,400	2.72	3	0
cyclic gmp Cyclic GMP: Guanosine cyclic 3',5'-(hydrogen phosphate). A guanine nucleotide containing one phosphate group which is esterified to the sugar moiety in both the 3'- and 5'-positions. It is a cellular regulatory agent and has been described as a second messenger. Its levels increase in response to a variety of hormones, including acetylcholine, insulin, and oxytocin and it has been found to activate specific protein kinases. (From Merck Index, 11th ed). 3',5'-cyclic GMP : A 3',5'-cyclic purine nucleotide in which the purine nucleobase is specified as guanidine.	3.55	8	0	3',5'-cyclic purine nucleotide; guanyl ribonucleotide	Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
deoxyguanosine [no description available]	2.71	3	0	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
guanosine diphosphate Guanosine Diphosphate: A guanine nucleotide containing two phosphate groups esterified to the sugar moiety.	3.37	7	0	guanosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	Escherichia coli metabolite; mouse metabolite; uncoupling protein inhibitor
guanosine triphosphate Guanosine Triphosphate: Guanosine 5'-(tetrahydrogen triphosphate). A guanine nucleotide containing three phosphate groups esterified to the sugar moiety.	5.61	24	0	guanosine 5'-phosphate; purine ribonucleoside 5'-triphosphate	Escherichia coli metabolite; mouse metabolite; uncoupling protein inhibitor
guanine [no description available]	2.35	2	0	2-aminopurines; oxopurine; purine nucleobase	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
guanosine ribonucleoside : Any nucleoside where the sugar component is D-ribose.	2.41	2	0	guanosines; purines D-ribonucleoside	fundamental metabolite
guanosine tetraphosphate Guanosine Tetraphosphate: Guanosine 5'-diphosphate 2'(3')-diphosphate. A guanine nucleotide containing four phosphate groups. Two phosphate groups are esterified to the sugar moiety in the 5' position and the other two in the 2' or 3' position. This nucleotide serves as a messenger to turn off the synthesis of ribosomal RNA when amino acids are not available for protein synthesis. Synonym: magic spot I.. guanosine 3',5'-bis(diphosphate) : A guanosine bisphosphate having diphosphate groups at both the 3' and 5'-positions.	2.02	1	0	guanosine bisphosphate	Escherichia coli metabolite; mouse metabolite
inosinic acid Inosine Monophosphate: Inosine 5'-Monophosphate. A purine nucleotide which has hypoxanthine as the base and one phosphate group esterified to the sugar moiety.	2.03	1	0	inosine phosphate; purine ribonucleoside 5'-monophosphate	Escherichia coli metabolite; human metabolite; mouse metabolite
inosine [no description available]	7.01	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.	2.73	3	0	folic acids; N-acyl-amino acid	human metabolite; mouse metabolite; nutrient
3-methyladenine N3-methyladenine: structure in first source	2.4	2	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.	5.1	44	0	nucleoside triphosphate analogue
pheophytin a pheophytin a: structure given in first source; RN given refers to (3S-(3alpha(2E,7S,11S),4beta,21beta))-isomer	3.59	7	0
clozapine Clozapine: A tricylic dibenzodiazepine, classified as an atypical antipsychotic agent. It binds several types of central nervous system receptors, and displays a unique pharmacological profile. Clozapine is a serotonin antagonist, with strong binding to 5-HT 2A/2C receptor subtype. It also displays strong affinity to several dopaminergic receptors, but shows only weak antagonism at the dopamine D2 receptor, a receptor commonly thought to modulate neuroleptic activity. Agranulocytosis is a major adverse effect associated with administration of this agent.. clozapine : A benzodiazepine that is 5H-dibenzo[b,e][1,4]diazepine substituted by a chloro group at position 8 and a 4-methylpiperazin-1-yl group at position 11. It is a second generation antipsychotic used in the treatment of psychiatric disorders like schizophrenia.	2.45	2	0	benzodiazepine; N-arylpiperazine; N-methylpiperazine; organochlorine compound	adrenergic antagonist; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; environmental contaminant; GABA antagonist; histamine antagonist; muscarinic antagonist; second generation antipsychotic; serotonergic antagonist; xenobiotic
olanzapine Olanzapine: A benzodiazepine derivative that binds SEROTONIN RECEPTORS; MUSCARINIC RECEPTORS; HISTAMINE H1 RECEPTORS; ADRENERGIC ALPHA-1 RECEPTORS; and DOPAMINE RECEPTORS. It is an antipsychotic agent used in the treatment of SCHIZOPHRENIA; BIPOLAR DISORDER; and MAJOR DEPRESSIVE DISORDER; it may also reduce nausea and vomiting in patients undergoing chemotherapy.. olanzapine : A benzodiazepine that is 10H-thieno[2,3-b][1,5]benzodiazepine substituted by a methyl group at position 2 and a 4-methylpiperazin-1-yl group at position 4.	2.04	1	0	benzodiazepine; N-arylpiperazine; N-methylpiperazine	antiemetic; dopaminergic antagonist; histamine antagonist; muscarinic antagonist; second generation antipsychotic; serotonergic antagonist; serotonin uptake inhibitor
zaprinast zaprinast: anaphylaxis inhibitor; structure	1.96	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.	3.06	5	0	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger
azaguanine Azaguanine: One of the early purine analogs showing antineoplastic activity. It functions as an antimetabolite and is easily incorporated into ribonucleic acids.. 8-azaguanine : A triazolopyrimidine that consists of 3,6-dihydro-7H-[1,2,3]triazolo[4,5-d]pyrimidine bearing amino and oxo substituents at positions 5 and 7 respectively.	1.93	1	0	nucleobase analogue; triazolopyrimidines	antimetabolite; antineoplastic agent; EC 2.4.2.1 (purine-nucleoside phosphorylase) inhibitor
guanylyl imidodiphosphate Guanylyl Imidodiphosphate: A non-hydrolyzable analog of GTP, in which the oxygen atom bridging the beta to the gamma phosphate is replaced by a nitrogen atom. It binds tightly to G-protein in the presence of Mg2+. The nucleotide is a potent stimulator of ADENYLYL CYCLASES.. guanosine 5'-[beta,gamma-imido]triphosphate : A nucleoside triphosphate analogue that is GTP in which the oxygen atom bridging the beta- to the gamma- phosphate is replaced by a nitrogen atom A non-hydrolyzable analog of GTP, it binds tightly to G-protein in the presence of Mg(2+).	1.98	1	0	nucleoside triphosphate analogue
2-amino-4-hydroxy-6,7-dimethyl-5,6,7,8-tetrahydropteridine 2-amino-4-hydroxy-6,7-dimethyl-5,6,7,8-tetrahydropteridine: used as a synthetic cofactor in place of tetrahydrofolate; RN given refers to parent cpd; structure	1.96	1	0	pterins
8-hydroxyguanosine 8-hydroxyguanosine: immunostimulant for B lymphocytes; structure given in first source	2	1	0	purine nucleoside
roseophilin roseophilin: isolated from Streptomyces griseovirdis; structure in first source	2.43	2	0
guanosine 5'-o-(2-thiodiphosphate) [no description available]	1.98	1	0	nucleoside diphosphate analogue
aprepitant Aprepitant: A morpholine neurokinin-1 (NK1) receptor antagonist that is used in the management of nausea and vomiting caused by DRUG THERAPY, and for the prevention of POSTOPERATIVE NAUSEA AND VOMITING.. aprepitant : A morpholine-based antiemetic, which is or the prevention of acute and delayed nausea and vomiting associated with initial and repeat courses of highly emetogenic cancer chemotherapy. Aprepitant is a selective high-affinity antagonist of human substance P/neurokinin 1 (NK1) receptors.	3.18	1	0	(trifluoromethyl)benzenes; cyclic acetal; morpholines; triazoles	antidepressant; antiemetic; neurokinin-1 receptor antagonist; peripheral nervous system drug; substance P receptor antagonist
xav939 XAV939: selectively inhibits beta-catenin-mediated transcription; structure in first source. XAV939 : A thiopyranopyrimidine in which a 7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidine skeleton is substituted at C-4 by a hydroxy group and at C-2 by a para-(trifluoromethyl)phenyl group.	2.05	1	0	(trifluoromethyl)benzenes; thiopyranopyrimidine	tankyrase inhibitor
trypan blue Trypan Blue: A diazo-naphthalene sulfonate that is widely used as a stain.. trypan blue : An organosulfonate salt that is the tetrasodium salt of 3,3'-[(3,3'-dimethylbiphenyl-4,4'-diyl)didiazene-2,1-diyl]bis(5-amino-4-hydroxynaphthalene-2,7-disulfonic acid).	2.07	1	0
nsc 614846 carbovir: structure given in first source; potent & selective anti-HIV agent. carbovir : Cyclopent-2-en-1-ylmethanol in which the 4-position is substituted by a 2-amino-6-hydroxy-9H-purin-9-yl group such that the two substitutents on the cyclopentene ring are in a cis relationship. The (-)-enantiomer, also known as carbovir, is a potent inhibitor of HIV replication replication in cell cultures.. (-)-carbovir : The (active) (-)-enantiomer of the carbocyclic analogue of 2',3'-dideoxy-2',3'-didehydroguanosine.	3.79	3	0	carbovir	HIV-1 reverse transcriptase inhibitor
bis(3',5')-cyclic diguanylic acid [no description available]	2.17	1	0	cyclic purine dinucleotide; guanyl ribonucleotide	immunomodulator; signalling molecule
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.	2.4	2	0	guanosines	biomarker
prodigiosin Prodigiosin: 4-Methoxy-5-((5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl)- 2,2'-bi-1H-pyrrole. A toxic, bright red tripyrrole pigment from Serratia marcescens and others. It has antibacterial, anticoccidial, antimalarial, and antifungal activities, but is used mainly as a biochemical tool.. prodigiosin : A member of the class of tripyrroles that is a red-coloured pigment with antibiotic properties produced by Serratia marcescens.	2.03	1	0
methyl inosine monophosphate methyl inosine monophosphate: potential immunotherapeutic for early HIV infection; structure given in first source	2.03	1	0
imidacloprid imidacloprid: systemic & contact insecticide exhibiting low mammalian toxicity; structure given in first source; it is one of the neonicotinoid insecticides, which acts as an antagonist by binding to postsynaptic nicotinic receptors in the insect central nervous system. imidacloprid : An imidazolidine that is N-nitroimidazolidin-2-imine bearing a (6-chloro-3-pyridinyl)methyl substituent at position 1.	2.1	1	0	imidacloprid; imidazolidines; monochloropyridine	environmental contaminant; genotoxin; neonicotinoid insectide; nicotinic acetylcholine receptor agonist; xenobiotic
nucleoside q Nucleoside Q: A modified nucleoside which is present in the first position of the anticodon of tRNA-tyrosine, tRNA-histidine, tRNA-asparagine and tRNA-aspartic acid of many organisms. It is believed to play a role in the regulatory function of tRNA. Nucleoside Q can be further modified to nucleoside Q*, which has a mannose or galactose moiety linked to position 4 of its cyclopentenediol moiety.. queuosine : A nucleoside found in tRNA that has an additional cyclopentenyl ring added via an NH group to the methyl group of 7-methyl-7-deazaguanosine. The cyclopentenyl ring may carry other substituents.	2.6	1	0	7-deazaguanine ribonucleoside
guanosine 5'-o-(1-thiotriphosphate) [no description available]	1.98	1	0
cyclic guanosine monophosphate-adenosine monophosphate 2'-3'-cGAMP : A cyclic purine dinucleotide that consists of AMP and GMP units cyclised via 3',5'- and 2',5'-linkages respectively.	2.25	1	0	adenyl ribonucleotide; cyclic purine dinucleotide; guanyl ribonucleotide
cyanine dye 3 cyanine dye 3: structures of Cy3 derivatives given in first source	1.99	1	0
trehazolin trehazolin: from Micromonospora strain SANK 62390; structure given in first source	2	1	0
avermectin avermectin: produced by actinomycete, Streptomyces avermitilis; structure; see also records for specific avermectins. avermectin : Any of the macrolides obtained as fermentation products from the bacterium Streptomyces avermitilis and consisting of a 16-membered macrocyclic backbone that is fused both benzofuran and spiroketal functions and contains a disaccharide substituent. They have significant anthelmintic and insecticidal properties.	2.44	2	0
eye [no description available]	4.5	4	0
quillaja saponins Quillaja Saponins: Natural detergents made up of a heterogeneous mixture of molecules having a triterpenoid core structure. They vary in aglycone (sapogenin) and sugar moieties, including glucose.	2.08	1	0
vincadifformine vincadifformine: RN given for (5alpha,12beta,19alpha)-isomer; structure in first source	2.15	1	0
wilforine wilforine: isolated from Tripterygium wilfordii; structure in first source. wilforine : An organic heteropentacyclic compound and pyridine alkaloid with formula C43H49NO18 originally isolated from the roots of Tripterygium wilfordii.	2.15	1	0
diepoxin sigma diepoxin sigma: structure in first source	1.99	1	0
picroside ii picroside II: RN given for (1aS-(1aalpha,1bbeta,2beta,5abeta,6beta,6abeta))-isomer; structure in first source	2.08	1	0
concanavalin a Concanavalin A: A MANNOSE/GLUCOSE binding lectin isolated from the jack bean (Canavalia ensiformis). It is a potent mitogen used to stimulate cell proliferation in lymphocytes, primarily T-lymphocyte, cultures.	3.36	7	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.	2.96	4	0
dinitrobenzenes Dinitrobenzenes: Benzene derivatives which are substituted with two nitro groups in the ortho, meta or para positions.	2.43	2	0
phosphorus radioisotopes Phosphorus Radioisotopes: Unstable isotopes of phosphorus that decay or disintegrate emitting radiation. P atoms with atomic weights 28-34 except 31 are radioactive phosphorus isotopes.	2.95	4	0
leoligin leoligin: inhibits intimal hyperplasia of venous bypass grafts; isolated from Edelweiss; structure in first source	2.1	1	0
preproenkephalin preproenkephalin: initial enkephalin precursor	2.03	1	0
pyrimidinones Pyrimidinones: Heterocyclic compounds known as 2-pyrimidones (or 2-hydroxypyrimidines) and 4-pyrimidones (or 4-hydroxypyrimidines) with the general formula C4H4N2O.	2.44	2	0
cochleamycin a cochleamycin A: isolated from Streptomyces; structure in first source	3.51	8	0
merrilactone a merrilactone A: structure in first source	3.51	1	0
tetrafluoroaluminate tetrafluoroaluminate: induces inositol phosphate formation	3.37	7	0
viridinomycin viridinomycin: crystalline antibiotic isolated from culture broth of Streptomyces viridochromogenes strain no. T-24146	2.43	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.	1.99	1	0
phenanthrenes Phenanthrenes: POLYCYCLIC AROMATIC HYDROCARBONS composed of three fused BENZENE rings.. phenanthrenes : Any benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof.	4.42	22	0

Condition	Relationship Strength	Studies	Trials
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	4.56	23	0
Disease Resistance The capacity of an organism to defend itself against pathological processes or the agents of those processes. This most often involves innate immunity whereby the organism responds to pathogens in a generic way. The term disease resistance is used most frequently when referring to plants.	10.15	411	0
Kahler Disease [description not available]	6.03	9	1
Multiple Myeloma A malignancy of mature PLASMA CELLS engaging in monoclonal immunoglobulin production. It is characterized by hyperglobulinemia, excess Bence-Jones proteins (free monoclonal IMMUNOGLOBULIN LIGHT CHAINS) in the urine, skeletal destruction, bone pain, and fractures. Other features include ANEMIA; HYPERCALCEMIA; and RENAL INSUFFICIENCY.	6.03	9	1
Amyloid Deposits [description not available]	2.31	1	0
Acute Confusional Senile Dementia [description not available]	4.97	14	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	8.36	105	1
Age-Related Memory Disorders [description not available]	3.62	8	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)	4.97	14	0
Memory Disorders Disturbances in registering an impression, in the retention of an acquired impression, or in the recall of an impression. Memory impairments are associated with DEMENTIA; CRANIOCEREBRAL TRAUMA; ENCEPHALITIS; ALCOHOLISM (see also ALCOHOL AMNESTIC DISORDER); SCHIZOPHRENIA; and other conditions.	3.62	8	0
Breast Cancer [description not available]	7.57	47	1
Breast Neoplasms Tumors or cancer of the human BREAST.	7.57	47	1
Diathesis [description not available]	7.19	31	1
Agnogenic Myeloid Metaplasia [description not available]	2.41	1	0
Acute Myelogenous Leukemia [description not available]	10.04	19	6
Myeloproliferative Disorders Conditions which cause proliferation of hemopoietically active tissue or of tissue which has embryonic hemopoietic potential. They all involve dysregulation of multipotent MYELOID PROGENITOR CELLS, most often caused by a mutation in the JAK2 PROTEIN TYROSINE KINASE.	2.41	1	0
Leukemia, Myeloid, Acute Clonal expansion of myeloid blasts in bone marrow, blood, and other tissue. Myeloid leukemias develop from changes in cells that normally produce NEUTROPHILS; BASOPHILS; EOSINOPHILS; and MONOCYTES.	10.04	19	6
Primary Myelofibrosis A de novo myeloproliferation arising from an abnormal stem cell. It is characterized by the replacement of bone marrow by fibrous tissue, a process that is mediated by CYTOKINES arising from the abnormal clone.	2.41	1	0
Bacterial Disease [description not available]	6.35	8	1
Bacterial Infections Infections by bacteria, general or unspecified.	6.35	8	1
2019 Novel Coronavirus Disease [description not available]	8.14	6	4
Viral Diseases [description not available]	3.25	6	0
Virus Diseases A general term for diseases caused by viruses.	3.25	6	0
Grippe [description not available]	16.89	167	22
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.	16.89	167	22
Cancer of Pancreas [description not available]	4.14	14	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).	4.14	14	0
Astrocytoma, Grade IV [description not available]	3.77	9	0
Glioblastoma A malignant form of astrocytoma histologically characterized by pleomorphism of cells, nuclear atypia, microhemorrhage, and necrosis. They may arise in any region of the central nervous system, with a predilection for the cerebral hemispheres, basal ganglia, and commissural pathways. Clinical presentation most frequently occurs in the fifth or sixth decade of life with focal neurologic signs or seizures.	3.77	9	0
Dehydration The condition that results from excessive loss of water from a living organism.	5.73	29	0
Acute Brain Injuries [description not available]	3.06	4	0
Cerebral Ischemia [description not available]	9.33	25	4
Brain Injuries Acute and chronic (see also BRAIN INJURIES, CHRONIC) injuries to the brain, including the cerebral hemispheres, CEREBELLUM, and BRAIN STEM. Clinical manifestations depend on the nature of injury. Diffuse trauma to the brain is frequently associated with DIFFUSE AXONAL INJURY or COMA, POST-TRAUMATIC. Localized injuries may be associated with NEUROBEHAVIORAL MANIFESTATIONS; HEMIPARESIS, or other focal neurologic deficits.	3.06	4	0
Brain Ischemia Localized reduction of blood flow to brain tissue due to arterial obstruction or systemic hypoperfusion. This frequently occurs in conjunction with brain hypoxia (HYPOXIA, BRAIN). Prolonged ischemia is associated with BRAIN INFARCTION.	9.33	25	4
Hyperglycemia, Postprandial Abnormally high BLOOD GLUCOSE level after a meal.	4.57	5	1
Hyperglycemia Abnormally high BLOOD GLUCOSE level.	4.57	5	1
Carcinoma, Anaplastic [description not available]	4.7	11	0
Cancer of Stomach [description not available]	8.77	12	4
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.	4.7	11	0
Stomach Neoplasms Tumors or cancer of the STOMACH.	8.77	12	4
Carcinoma, Ductal, Pancreatic [description not available]	2.63	2	0
Carcinoma, Pancreatic Ductal Carcinoma that arises from the PANCREATIC DUCTS. It accounts for the majority of cancers derived from the PANCREAS.	2.63	2	0
Degenerative Diseases, Central Nervous System [description not available]	4.37	4	0
Neurodegenerative Diseases Hereditary and sporadic conditions which are characterized by progressive nervous system dysfunction. These disorders are often associated with atrophy of the affected central or peripheral nervous system structures.	4.37	4	0
Infections, Nematode [description not available]	3.17	5	0
Cyst [description not available]	2.76	2	0
Acute Liver Injury, Drug-Induced [description not available]	5.14	3	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.	5.14	3	1
Concomitant Strabismus [description not available]	2.66	3	0
Strabismus Misalignment of the visual axes of the eyes. In comitant strabismus the degree of ocular misalignment does not vary with the direction of gaze. In noncomitant strabismus the degree of misalignment varies depending on direction of gaze or which eye is fixating on the target. (Miller, Walsh & Hoyt's Clinical Neuro-Ophthalmology, 4th ed, p641)	2.66	3	0
Stunted Growth [description not available]	2.41	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.	2.41	1	0
Myelomonocytic Leukemia, Chronic [description not available]	6.72	3	3
Leukemia, Myelomonocytic, Chronic A myelodysplastic-myeloproliferative disease characterized by monocytosis, increased monocytes in the bone marrow, variable degrees of dysplasia, but an absence of immature granulocytes in the blood.	6.72	3	3
Malignant Melanoma [description not available]	6.36	14	1
Melanoma A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)	6.36	14	1
Peripheral Nerve Diseases [description not available]	3.66	3	0
Peripheral Nervous System Diseases Diseases of the peripheral nerves external to the brain and spinal cord, which includes diseases of the nerve roots, ganglia, plexi, autonomic nerves, sensory nerves, and motor nerves.	3.66	3	0
Diabetes Mellitus, Adult-Onset [description not available]	6.58	9	2
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.	6.58	9	2
Innate Inflammatory Response [description not available]	12.97	62	17
Cancer of Liver [description not available]	4.56	24	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.	17.97	62	17
Liver Neoplasms Tumors or cancer of the LIVER.	4.56	24	0
Benign Neoplasms [description not available]	12.7	65	3
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.	12.7	65	3
Acute Edematous Pancreatitis [description not available]	2.39	2	0
Acute Disease Disease having a short and relatively severe course.	3.62	3	0
Pancreatitis INFLAMMATION of the PANCREAS. Pancreatitis is classified as acute unless there are computed tomographic or endoscopic retrograde cholangiopancreatographic findings of CHRONIC PANCREATITIS (International Symposium on Acute Pancreatitis, Atlanta, 1992). The two most common forms of acute pancreatitis are ALCOHOLIC PANCREATITIS and gallstone pancreatitis.	7.39	2	0
Hypertriglyceridemia A condition of elevated levels of TRIGLYCERIDES in the blood.	2.41	1	0
Cancer of Lung [description not available]	5.37	21	0
Lung Neoplasms Tumors or cancer of the LUNG.	5.37	21	0
Germinoblastoma [description not available]	5.83	8	1
Lymphoma A general term for various neoplastic diseases of the lymphoid tissue.	5.83	8	1
Acariasis [description not available]	2.93	4	0
Anosmia Complete or severe loss of the subjective sense of smell. Loss of smell may be caused by many factors such as a cold, allergy, OLFACTORY NERVE DISEASES, viral RESPIRATORY TRACT INFECTIONS (e.g., COVID-19), aging and various neurological disorders (e.g., ALZHEIMER DISEASE).	2.6	1	0
Dermatitis Any inflammation of the skin.	2.88	4	0
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	2.97	4	0
Cancer of Intestines [description not available]	2.21	1	0
Intestinal Neoplasms Tumors or cancer of the INTESTINES.	2.21	1	0
Neuroendocrine Tumors Tumors whose cells possess secretory granules and originate from the neuroectoderm, i.e., the cells of the ectoblast or epiblast that program the neuroendocrine system. Common properties across most neuroendocrine tumors include ectopic hormone production (often via APUD CELLS), the presence of tumor-associated antigens, and isozyme composition.	2.21	1	0
Carcinoma, Epidermoid [description not available]	3.63	9	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)	3.63	9	0
Critical Illness A disease or state in which death is possible or imminent.	3.34	6	0
Eosinophilia, Tropical [description not available]	2.7	3	0
Ascites Accumulation or retention of free fluid within the peritoneal cavity.	3.2	6	0
Enteritis Inflammation of any segment of the SMALL INTESTINE.	2.21	1	0
Eosinophilia Abnormal increase of EOSINOPHILS in the blood, tissues or organs.	2.7	3	0
Gastritis Inflammation of the GASTRIC MUCOSA, a lesion observed in a number of unrelated disorders.	2.21	1	0
Ankylosing Spondylarthritis [description not available]	2.21	1	0
Spondylitis, Ankylosing A chronic inflammatory condition affecting the axial joints, such as the SACROILIAC JOINT and other intervertebral or costovertebral joints. It occurs predominantly in young males and is characterized by pain and stiffness of joints (ANKYLOSIS) with inflammation at tendon insertions.	2.21	1	0
Infection [description not available]	2.81	3	0
Infections Invasion of the host organism by microorganisms or their toxins or by parasites that can cause pathological conditions or diseases.	2.81	3	0
Canine Diseases [description not available]	2.71	3	0
Cancer of Mouth [description not available]	2.48	2	0
Mouth Neoplasms Tumors or cancer of the MOUTH.	2.48	2	0
Anesthesia A state characterized by loss of feeling or sensation. This depression of nerve function is usually the result of pharmacologic action and is induced to allow performance of surgery or other painful procedures.	2.37	2	0
Cancer of Skin [description not available]	3.69	10	0
Skin Neoplasms Tumors or cancer of the SKIN.	3.69	10	0
Albinism, Tyrosinase-Negative [description not available]	2.21	1	0
Albinism, Oculocutaneous Heterogeneous group of autosomal recessive disorders comprising at least four recognized types, all having in common varying degrees of hypopigmentation of the skin, hair, and eyes. The two most common are the tyrosinase-positive and tyrosinase-negative types.	2.21	1	0
Tetraploid [description not available]	2.66	2	0
Allergic Rhinitis [description not available]	5.02	2	1
Rhinitis, Allergic An inflammation of the NASAL MUCOSA triggered by ALLERGENS.	5.02	2	1
Cardiac Hypertrophy Enlargement of the HEART due to chamber HYPERTROPHY, an increase in wall thickness without an increase in the number of cells (MYOCYTES, CARDIAC). It is the result of increase in myocyte size, mitochondrial and myofibrillar mass, as well as changes in extracellular matrix.	2.52	2	0
Cardiomegaly Enlargement of the HEART, usually indicated by a cardiothoracic ratio above 0.50. Heart enlargement may involve the right, the left, or both HEART VENTRICLES or HEART ATRIA. Cardiomegaly is a nonspecific symptom seen in patients with chronic systolic heart failure (HEART FAILURE) or several forms of CARDIOMYOPATHIES.	2.52	2	0
Experimental Lung Inflammation Inflammation of any part, segment or lobe, of the lung parenchyma.	3.86	4	0
Pneumonia Infection of the lung often accompanied by inflammation.	3.86	4	0
Lung Adenocarcinoma [description not available]	2.82	3	0
Adenocarcinoma of Lung A carcinoma originating in the lung and the most common lung cancer type in never-smokers. Malignant cells exhibit distinct features such as glandular epithelial, or tubular morphology. Mutations in KRAS, EGFR, BRAF, and ERBB2 genes are associated with this cancer.	2.82	3	0
Pneumonia, Viral Inflammation of the lung parenchyma that is caused by a viral infection.	8.68	11	4
Microsatellite Instability The occurrence of highly polymorphic mono- and dinucleotide MICROSATELLITE REPEATS in somatic cells. It is a form of genome instability associated with defects in DNA MISMATCH REPAIR.	2.25	1	0
Colorectal Cancer [description not available]	7.18	12	1
Cancer of Endometrium [description not available]	3.06	4	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.	7.18	12	1
Endometrial Neoplasms Tumors or cancer of ENDOMETRIUM, the mucous lining of the UTERUS. These neoplasms can be benign or malignant. Their classification and grading are based on the various cell types and the percent of undifferentiated cells.	3.06	4	0
Cough A sudden, audible expulsion of air from the lungs through a partially closed glottis, preceded by inhalation. It is a protective response that serves to clear the trachea, bronchi, and/or lungs of irritants and secretions, or to prevent aspiration of foreign materials into the lungs.	5.81	23	1
Abortion, Recurrent [description not available]	2.25	1	0
Abortion, Habitual Three or more consecutive spontaneous abortions.	2.25	1	0
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	7.65	35	1
Leukemia, Lymphocytic, Chronic, T Cell [description not available]	2.31	1	0
Leukemia, Prolymphocytic, T-Cell A lymphoid leukemia characterized by a profound LYMPHOCYTOSIS with or without LYMPHADENOPATHY, hepatosplenomegaly, frequently rapid progression, and short survival. It was formerly called T-cell chronic lymphocytic leukemia.	2.31	1	0
Blood Pressure, High [description not available]	8.44	26	6
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.	8.44	26	6
Allergic Encephalomyelitis [description not available]	3.37	7	0
Bone Loss, Osteoclastic [description not available]	2.25	1	0
Absence Status [description not available]	2.61	2	0
Status Epilepticus A prolonged seizure or seizures repeated frequently enough to prevent recovery between episodes occurring over a period of 20-30 minutes. The most common subtype is generalized tonic-clonic status epilepticus, a potentially fatal condition associated with neuronal injury and respiratory and metabolic dysfunction. Nonconvulsive forms include petit mal status and complex partial status, which may manifest as behavioral disturbances. Simple partial status epilepticus consists of persistent motor, sensory, or autonomic seizures that do not impair cognition (see also EPILEPSIA PARTIALIS CONTINUA). Subclinical status epilepticus generally refers to seizures occurring in an unresponsive or comatose individual in the absence of overt signs of seizure activity. (From N Engl J Med 1998 Apr 2;338(14):970-6; Neurologia 1997 Dec;12 Suppl 6:25-30)	2.61	2	0
Experimental Neoplasms [description not available]	7.3	25	1
Cell Transformation, Neoplastic Cell changes manifested by escape from control mechanisms, increased growth potential, alterations in the cell surface, karyotypic abnormalities, morphological and biochemical deviations from the norm, and other attributes conferring the ability to invade, metastasize, and kill.	3.12	5	0
Cancer of Cervix [description not available]	3.61	8	0
Uterine Cervical Neoplasms Tumors or cancer of the UTERINE CERVIX.	3.61	8	0
Infections, Coronavirus [description not available]	8.26	6	4
Coronavirus Infections Virus diseases caused by the CORONAVIRUS genus. Some specifics include transmissible enteritis of turkeys (ENTERITIS, TRANSMISSIBLE, OF TURKEYS); FELINE INFECTIOUS PERITONITIS; and transmissible gastroenteritis of swine (GASTROENTERITIS, TRANSMISSIBLE, OF SWINE).	8.26	6	4
Cancer of Esophagus [description not available]	5.46	4	1
Esophageal Neoplasms Tumors or cancer of the ESOPHAGUS.	5.46	4	1
Cancer of Prostate [description not available]	5.32	20	0
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	5.32	20	0
Hepatocellular Carcinoma [description not available]	4.5	23	0
Lymph Node Metastasis [description not available]	3.1	4	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.	4.5	23	0
Leukocytopenia [description not available]	2.31	1	0
Leukopenia A decrease in the number of LEUKOCYTES in a blood sample below the normal range (LEUKOCYTE COUNT less than 4000).	2.31	1	0
Sterility, Male [description not available]	2.25	1	0
Infertility, Male The inability of the male to effect FERTILIZATION of an OVUM after a specified period of unprotected intercourse. Male sterility is permanent infertility.	2.25	1	0
Alopecia Cicatrisata [description not available]	4.58	2	2
Alopecia Absence of hair from areas where it is normally present.	4.58	2	2
Respiratory Tract Diseases Diseases involving the RESPIRATORY SYSTEM.	5.79	4	2
Cancer of Ovary [description not available]	6.4	14	1
Ovarian Neoplasms Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.	6.4	14	1
Genetic Predisposition [description not available]	5.59	6	1
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	8.31	43	3
Chronic Illness [description not available]	6.13	6	2
Cardiac Death [description not available]	4.72	1	1
Chronic Hepatitis C [description not available]	7.84	4	4
Cerebral Infarction, Middle Cerebral Artery [description not available]	6.17	11	1
Cardiac Remodeling, Ventricular [description not available]	5.36	4	1
Acute Relapsing Multiple Sclerosis [description not available]	4.72	1	1
Acute Kidney Failure [description not available]	4.85	2	1
Peripheral Arterial Diseases [description not available]	4.72	1	1
Co-infection [description not available]	5.52	5	1
Epithelial Ovarian Cancer [description not available]	4.87	2	1
ALS - Amyotrophic Lateral Sclerosis [description not available]	5.1	3	1
Adjuvant Arthritis [description not available]	5.57	6	1
Rheumatoid Arthritis [description not available]	6.02	6	1
Asthma, Bronchial [description not available]	8.12	7	5
Benign Neoplasms, Brain [description not available]	5.82	7	1
Cardiomyopathy, Hypertrophic Obstructive [description not available]	4.72	1	1
Catarrh Inflammation of a mucous membrane with increased flow of mucous in humans or animals. Catarrh is used mostly in a historical context.	4.72	1	1
Endometrioma An enlarged area of ENDOMETRIOSIS that resembles a tumor. It is usually found in the OVARY. When it is filled with old blood, it is known as a chocolate cyst.	5.15	3	1
E coli Infections [description not available]	4.8	2	1
Fish Diseases Diseases of freshwater, marine, hatchery or aquarium fish. This term includes diseases of both teleosts (true fish) and elasmobranchs (sharks, rays and skates).	4.99	2	1
Berger Disease [description not available]	4.72	1	1
Hepatitis, Viral, Non-A, Non-B, Parenterally-Transmitted [description not available]	5.33	4	1
Central Hypothyroidism [description not available]	4.99	3	1
Chronic Kidney Failure [description not available]	4.84	2	1
Cirrhosis, Liver [description not available]	4.94	2	1
Libman-Sacks Disease [description not available]	4.84	2	1
Age-Related Macular Degeneration [description not available]	4.72	1	1
MS (Multiple Sclerosis) [description not available]	5.22	4	1
Arthritis, Degenerative [description not available]	5.38	2	2
Complication, Postoperative [description not available]	7.68	5	4
Sarcoma, Epithelioid [description not available]	6.09	6	2
Shock, Cardiogenic Shock resulting from diminution of cardiac output in heart disease.	4.84	2	1
Sinus Infections [description not available]	4.72	1	1
Infections, Staphylococcal [description not available]	4.7	2	1
Cancer of the Thyroid [description not available]	5	3	1
Injury, Ischemia-Reperfusion [description not available]	8.82	14	4
HIV Coinfection [description not available]	10.06	12	9
Plasmodium falciparum Malaria [description not available]	5.01	3	1
Bacterial Infections, Gram-Negative [description not available]	4.72	1	1
Bacterial Infections, Gram-Positive [description not available]	4.72	1	1
Low Back Ache [description not available]	4.72	1	1
Heart Disease, Ischemic [description not available]	5.42	5	1
Local Neoplasm Recurrence [description not available]	9.33	8	5
Invasiveness, Neoplasm [description not available]	6.31	12	1
Bucket Handle Tears [description not available]	4.72	1	1
Carcinoma, Ovarian Epithelial A malignant neoplasm that originates in cells on the surface EPITHELIUM of the ovary and is the most common form of ovarian cancer. There are five histologic subtypes: papillary serous, endometrioid, mucinous, clear cell, and transitional cell. Mutations in BRCA1, OPCML, PRKN, PIK3CA, AKT1, CTNNB1, RRAS2, and CDH1 genes are associated with this cancer.	4.87	2	1
Amyotrophic Lateral Sclerosis A degenerative disorder affecting upper MOTOR NEURONS in the brain and lower motor neurons in the brain stem and SPINAL CORD. Disease onset is usually after the age of 50 and the process is usually fatal within 3 to 6 years. Clinical manifestations include progressive weakness, atrophy, FASCICULATION, hyperreflexia, DYSARTHRIA, dysphagia, and eventual paralysis of respiratory function. Pathologic features include the replacement of motor neurons with fibrous ASTROCYTES and atrophy of anterior SPINAL NERVE ROOTS and corticospinal tracts. (From Adams et al., Principles of Neurology, 6th ed, pp1089-94)	5.1	3	1
Arthritis, Rheumatoid A chronic systemic disease, primarily of the joints, marked by inflammatory changes in the synovial membranes and articular structures, widespread fibrinoid degeneration of the collagen fibers in mesenchymal tissues, and by atrophy and rarefaction of bony structures. Etiology is unknown, but autoimmune mechanisms have been implicated.	6.02	6	1
Asthma A form of bronchial disorder with three distinct components: airway hyper-responsiveness (RESPIRATORY HYPERSENSITIVITY), airway INFLAMMATION, and intermittent AIRWAY OBSTRUCTION. It is characterized by spasmodic contraction of airway smooth muscle, WHEEZING, and dyspnea (DYSPNEA, PAROXYSMAL).	8.12	7	5
Brain Neoplasms Neoplasms of the intracranial components of the central nervous system, including the cerebral hemispheres, basal ganglia, hypothalamus, thalamus, brain stem, and cerebellum. Brain neoplasms are subdivided into primary (originating from brain tissue) and secondary (i.e., metastatic) forms. Primary neoplasms are subdivided into benign and malignant forms. In general, brain tumors may also be classified by age of onset, histologic type, or presenting location in the brain.	5.82	7	1
Cardiomyopathy, Hypertrophic A form of CARDIAC MUSCLE disease, characterized by left and/or right ventricular hypertrophy (HYPERTROPHY, LEFT VENTRICULAR; HYPERTROPHY, RIGHT VENTRICULAR), frequent asymmetrical involvement of the HEART SEPTUM, and normal or reduced left ventricular volume. Risk factors include HYPERTENSION; AORTIC STENOSIS; and gene MUTATION; (FAMILIAL HYPERTROPHIC CARDIOMYOPATHY).	4.72	1	1
Cardiovascular Diseases Pathological conditions involving the CARDIOVASCULAR SYSTEM including the HEART; the BLOOD VESSELS; or the PERICARDIUM.	5.69	3	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).	6.13	6	2
Common Cold A catarrhal disorder of the upper respiratory tract, which may be viral or a mixed infection. It generally involves a runny nose, nasal congestion, and sneezing.	4.72	1	1
Electrolytes Substances that dissociate into two or more ions, to some extent, in water. Solutions of electrolytes thus conduct an electric current and can be decomposed by it (ELECTROLYSIS). (Grant & Hackh's Chemical Dictionary, 5th ed)	5.58	6	1
Endometriosis A condition in which functional endometrial tissue is present outside the UTERUS. It is often confined to the PELVIS involving the OVARY, the ligaments, cul-de-sac, and the uterovesical peritoneum.	5.15	3	1
Escherichia coli Infections Infections with bacteria of the species ESCHERICHIA COLI.	4.8	2	1
Glomerulonephritis, IGA A chronic form of glomerulonephritis characterized by deposits of predominantly IMMUNOGLOBULIN A in the mesangial area (GLOMERULAR MESANGIUM). Deposits of COMPLEMENT C3 and IMMUNOGLOBULIN G are also often found. Clinical features may progress from asymptomatic HEMATURIA to END-STAGE KIDNEY DISEASE.	4.72	1	1
Hepatitis C INFLAMMATION of the LIVER in humans caused by HEPATITIS C VIRUS, a single-stranded RNA virus. Its incubation period is 30-90 days. Hepatitis C is transmitted primarily by contaminated blood parenterally and is often associated with transfusion and intravenous drug abuse. However, in a significant number of cases, the source of hepatitis C infection is unknown.	10.33	4	1
Hypothyroidism A syndrome that results from abnormally low secretion of THYROID HORMONES from the THYROID GLAND, leading to a decrease in BASAL METABOLIC RATE. In its most severe form, there is accumulation of MUCOPOLYSACCHARIDES in the SKIN and EDEMA, known as MYXEDEMA. It may be primary or secondary due to other pituitary disease, or hypothalamic dysfunction.	4.99	3	1
Intermittent Claudication A symptom complex characterized by pain and weakness in SKELETAL MUSCLE group associated with exercise, such as leg pain and weakness brought on by walking. Such muscle limpness disappears after a brief rest and is often relates to arterial STENOSIS; muscle ISCHEMIA; and accumulation of LACTATE.	4.72	1	1
Kidney Failure, Chronic The end-stage of CHRONIC RENAL INSUFFICIENCY. It is characterized by the severe irreversible kidney damage (as measured by the level of PROTEINURIA) and the reduction in GLOMERULAR FILTRATION RATE to less than 15 ml per min (Kidney Foundation: Kidney Disease Outcome Quality Initiative, 2002). These patients generally require HEMODIALYSIS or KIDNEY TRANSPLANTATION.	4.84	2	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.	4.94	2	1
Lupus Erythematosus, Systemic A chronic, relapsing, inflammatory, and often febrile multisystemic disorder of connective tissue, characterized principally by involvement of the skin, joints, kidneys, and serosal membranes. It is of unknown etiology, but is thought to represent a failure of the regulatory mechanisms of the autoimmune system. The disease is marked by a wide range of system dysfunctions, an elevated erythrocyte sedimentation rate, and the formation of LE cells in the blood or bone marrow.	4.84	2	1
Macular Degeneration Degenerative changes in the RETINA usually of older adults which results in a loss of vision in the center of the visual field (the MACULA LUTEA) because of damage to the retina. It occurs in dry and wet forms.	4.72	1	1
Multiple Sclerosis An autoimmune disorder mainly affecting young adults and characterized by destruction of myelin in the central nervous system. Pathologic findings include multiple sharply demarcated areas of demyelination throughout the white matter of the central nervous system. Clinical manifestations include visual loss, extra-ocular movement disorders, paresthesias, loss of sensation, weakness, dysarthria, spasticity, ataxia, and bladder dysfunction. The usual pattern is one of recurrent attacks followed by partial recovery (see MULTIPLE SCLEROSIS, RELAPSING-REMITTING), but acute fulminating and chronic progressive forms (see MULTIPLE SCLEROSIS, CHRONIC PROGRESSIVE) also occur. (Adams et al., Principles of Neurology, 6th ed, p903)	5.22	4	1
Neuroblastoma A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)	6.33	14	1
Osteoarthritis A progressive, degenerative joint disease, the most common form of arthritis, especially in older persons. The disease is thought to result not from the aging process but from biochemical changes and biomechanical stresses affecting articular cartilage. In the foreign literature it is often called osteoarthrosis deformans.	5.38	2	2
Postoperative Complications Pathologic processes that affect patients after a surgical procedure. They may or may not be related to the disease for which the surgery was done, and they may or may not be direct results of the surgery.	7.68	5	4
Sarcoma A connective tissue neoplasm formed by proliferation of mesodermal cells; it is usually highly malignant.	6.09	6	2
Sinusitis Inflammation of the NASAL MUCOSA in one or more of the PARANASAL SINUSES.	4.72	1	1
Staphylococcal Infections Infections with bacteria of the genus STAPHYLOCOCCUS.	4.7	2	1
Thyroid Neoplasms Tumors or cancer of the THYROID GLAND.	5	3	1
Reperfusion Injury Adverse functional, metabolic, or structural changes in tissues that result from the restoration of blood flow to the tissue (REPERFUSION) following ISCHEMIA.	8.82	14	4
HIV Infections Includes the spectrum of human immunodeficiency virus infections that range from asymptomatic seropositivity, thru AIDS-related complex (ARC), to acquired immunodeficiency syndrome (AIDS).	10.06	12	9
Malaria, Falciparum Malaria caused by PLASMODIUM FALCIPARUM. This is the severest form of malaria and is associated with the highest levels of parasites in the blood. This disease is characterized by irregularly recurring febrile paroxysms that in extreme cases occur with acute cerebral, renal, or gastrointestinal manifestations.	5.01	3	1
Gram-Negative Bacterial Infections Infections caused by bacteria that show up as pink (negative) when treated by the gram-staining method.	4.72	1	1
Gram-Positive Bacterial Infections Infections caused by bacteria that retain the crystal violet stain (positive) when treated by the gram-staining method.	4.72	1	1
Low Back Pain Acute or chronic pain in the lumbar or sacral regions, which may be associated with musculo-ligamentous SPRAINS AND STRAINS; INTERVERTEBRAL DISK DISPLACEMENT; and other conditions.	4.72	1	1
Myocardial Ischemia A disorder of cardiac function caused by insufficient blood flow to the muscle tissue of the heart. The decreased blood flow may be due to narrowing of the coronary arteries (CORONARY ARTERY DISEASE), to obstruction by a thrombus (CORONARY THROMBOSIS), or less commonly, to diffuse narrowing of arterioles and other small vessels within the heart. Severe interruption of the blood supply to the myocardial tissue may result in necrosis of cardiac muscle (MYOCARDIAL INFARCTION).	5.42	5	1
Hepatitis C, Chronic INFLAMMATION of the LIVER in humans that is caused by HEPATITIS C VIRUS lasting six months or more. Chronic hepatitis C can lead to LIVER CIRRHOSIS.	7.84	4	4
Infarction, Middle Cerebral Artery NECROSIS occurring in the MIDDLE CEREBRAL ARTERY distribution system which brings blood to the entire lateral aspects of each CEREBRAL HEMISPHERE. Clinical signs include impaired cognition; APHASIA; AGRAPHIA; weak and numbness in the face and arms, contralaterally or bilaterally depending on the infarction.	6.17	11	1
Multiple Sclerosis, Relapsing-Remitting The most common clinical variant of MULTIPLE SCLEROSIS, characterized by recurrent acute exacerbations of neurologic dysfunction followed by partial or complete recovery. Common clinical manifestations include loss of visual (see OPTIC NEURITIS), motor, sensory, or bladder function. Acute episodes of demyelination may occur at any site in the central nervous system, and commonly involve the optic nerves, spinal cord, brain stem, and cerebellum. (Adams et al., Principles of Neurology, 6th ed, pp903-914)	4.72	1	1
Sarcopenia Progressive decline in muscle mass due to aging which results in decreased functional capacity of muscles.	4.72	1	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.	4.85	2	1
Peripheral Arterial Disease Lack of perfusion in the EXTREMITIES resulting from atherosclerosis. It is characterized by INTERMITTENT CLAUDICATION, and an ANKLE BRACHIAL INDEX of 0.9 or less.	4.72	1	1
Acute Pain Intensely discomforting, distressful, or agonizing sensation associated with trauma or disease, with well-defined location, character, and timing.	4.72	1	1
Disease Exacerbation [description not available]	5.2	10	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.	3.05	4	0
Absence Seizure [description not available]	5.35	22	0
Seizures Clinical or subclinical disturbances of cortical function due to a sudden, abnormal, excessive, and disorganized discharge of brain cells. Clinical manifestations include abnormal motor, sensory and psychic phenomena. Recurrent seizures are usually referred to as EPILEPSY or seizure disorder.	5.35	22	0
Depression Depressive states usually of moderate intensity in contrast with MAJOR DEPRESSIVE DISORDER present in neurotic and psychotic disorders.	3.56	8	0
Metastase [description not available]	3.42	7	0
Angiogenesis, Pathologic [description not available]	4.66	9	0
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	3.42	7	0
Polyploid [description not available]	3.6	8	0
Alcohol Abuse [description not available]	5.37	9	0
Allodynia [description not available]	5.62	9	2
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)	5.37	9	0
Glial Cell Tumors [description not available]	3.52	8	0
Glioma Benign and malignant central nervous system neoplasms derived from glial cells (i.e., astrocytes, oligodendrocytes, and ependymocytes). Astrocytes may give rise to astrocytomas (ASTROCYTOMA) or glioblastoma multiforme (see GLIOBLASTOMA). Oligodendrocytes give rise to oligodendrogliomas (OLIGODENDROGLIOMA) and ependymocytes may undergo transformation to become EPENDYMOMA; CHOROID PLEXUS NEOPLASMS; or colloid cysts of the third ventricle. (From Escourolle et al., Manual of Basic Neuropathology, 2nd ed, p21)	3.52	8	0
Cognitive Decline [description not available]	2.31	1	0
Amnesia-Memory Loss [description not available]	2.5	2	0
Amnesia Pathologic partial or complete loss of the ability to recall past experiences (AMNESIA, RETROGRADE) or to form new memories (AMNESIA, ANTEROGRADE). This condition may be of organic or psychologic origin. Organic forms of amnesia are usually associated with dysfunction of the DIENCEPHALON or HIPPOCAMPUS. (From Adams et al., Principles of Neurology, 6th ed, pp426-7)	2.5	2	0
Cognitive Dysfunction Diminished or impaired mental and/or intellectual function.	2.31	1	0
Opportunistic Infections An infection caused by an organism which becomes pathogenic under certain conditions, e.g., during immunosuppression.	2.31	1	0
Infections, Pseudomonas [description not available]	2.98	4	0
Pseudomonas Infections Infections with bacteria of the genus PSEUDOMONAS.	2.98	4	0
Apoplexy [description not available]	3.03	4	0
Stroke A group of pathological conditions characterized by sudden, non-convulsive loss of neurological function due to BRAIN ISCHEMIA or INTRACRANIAL HEMORRHAGES. Stroke is classified by the type of tissue NECROSIS, such as the anatomic location, vasculature involved, etiology, age of the affected individual, and hemorrhagic vs. non-hemorrhagic nature. (From Adams et al., Principles of Neurology, 6th ed, pp777-810)	3.03	4	0
Albuminuria The presence of albumin in the urine, an indicator of KIDNEY DISEASES.	2.44	2	0
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	4.51	5	1
Acute Promyelocytic Leukemia [description not available]	2.31	1	0
Leukemia, Promyelocytic, Acute An acute myeloid leukemia in which abnormal PROMYELOCYTES predominate. It is frequently associated with DISSEMINATED INTRAVASCULAR COAGULATION.	2.31	1	0
Carcinoma, Squamous Cell of Head and Neck [description not available]	3.26	5	0
Cancer of the Tongue [description not available]	2.31	1	0
Squamous Cell Carcinoma of Head and Neck The most common type of head and neck carcinoma that originates from cells on the surface of the NASAL CAVITY; MOUTH; PARANASAL SINUSES, SALIVARY GLANDS, and LARYNX. Mutations in TNFRSF10B, PTEN, and ING1 genes are associated with this cancer.	3.26	5	0
Tongue Neoplasms Tumors or cancer of the TONGUE.	2.31	1	0
Dysmyelopoietic Syndromes [description not available]	7.69	6	4
Myelodysplastic Syndromes Clonal hematopoietic stem cell disorders characterized by dysplasia in one or more hematopoietic cell lineages. They predominantly affect patients over 60, are considered preleukemic conditions, and have high probability of transformation into ACUTE MYELOID LEUKEMIA.	7.69	6	4
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.	2.31	1	0
Fungal Diseases [description not available]	3.29	6	0
Mycoses Diseases caused by FUNGI.	3.29	6	0
Chronic Pancreatitis [description not available]	2.31	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.	2.31	1	0
Carcinoma, Non-Small Cell Lung [description not available]	2.99	4	0
Carcinoma, Non-Small-Cell Lung A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.	2.99	4	0
ER-Negative PR-Negative HER2-Negative Breast Cancer [description not available]	2.85	3	0
Triple Negative Breast Neoplasms Breast neoplasms that do not express ESTROGEN RECEPTORS; PROGESTERONE RECEPTORS; and do not overexpress the NEU RECEPTOR/HER-2 PROTO-ONCOGENE PROTEIN.	2.85	3	0
B-Cell Chronic Lymphocytic Leukemia [description not available]	3.19	5	0
Leukemia, Lymphocytic, Chronic, B-Cell A chronic leukemia characterized by abnormal B-lymphocytes and often generalized lymphadenopathy. In patients presenting predominately with blood and bone marrow involvement it is called chronic lymphocytic leukemia (CLL); in those predominately with enlarged lymph nodes it is called small lymphocytic lymphoma. These terms represent spectrums of the same disease.	3.19	5	0
Carcinoma, Oat Cell [description not available]	2.31	1	0
Carcinoma, Small Cell An anaplastic, highly malignant, and usually bronchogenic carcinoma composed of small ovoid cells with scanty neoplasm. It is characterized by a dominant, deeply basophilic nucleus, and absent or indistinct nucleoli. (From Stedman, 25th ed; Holland et al., Cancer Medicine, 3d ed, p1286-7)	2.31	1	0
Neoplastic Processes The pathological mechanisms and forms taken by tissue during degeneration into a neoplasm and its subsequent activity.	3.23	1	0
Liver Dysfunction [description not available]	2.31	1	0
Liver Diseases Pathological processes of the LIVER.	2.31	1	0
Choroid Neovascularization [description not available]	2.25	1	0
Rhabdoid Tumor A rare but highly lethal childhood tumor found almost exclusively in infants. Histopathologically, it resembles RHABDOMYOSARCOMA but the tumor cells are not of myogenic origin. Although it arises primarily in the kidney, it may be found in other parts of the body. The rhabdoid cytomorphology is believed to be the expression of a very primitive malignant cell. (From Holland et al., Cancer Medicine, 3d ed, p2210)	2.31	1	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.	3.25	6	0
Adult GM1 Gangliosidosis [description not available]	2.55	2	0
Gangliosidosis, GM1 An autosomal recessive neurodegenerative disorder caused by the absence or deficiency of BETA-GALACTOSIDASE. It is characterized by intralysosomal accumulation of G(M1) GANGLIOSIDE and oligosaccharides, primarily in neurons of the central nervous system. The infantile form is characterized by MUSCLE HYPOTONIA, poor psychomotor development, HIRSUTISM, hepatosplenomegaly, and facial abnormalities. The juvenile form features HYPERACUSIS; SEIZURES; and psychomotor retardation. The adult form features progressive DEMENTIA; ATAXIA; and MUSCLE SPASTICITY. (From Menkes, Textbook of Child Neurology, 5th ed, pp96-7)	2.55	2	0
Anasarca [description not available]	5.39	14	1
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	5.39	14	1
Hormone-Dependent Neoplasms [description not available]	2.15	1	0
Carcinoma, Ehrlich Tumor A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.	3.96	14	0
Food Poisoning [description not available]	2.58	2	0
Adenocarcinoma, Basal Cell [description not available]	4.87	13	0
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	4.87	13	0
Nasopharyngeal Carcinoma A carcinoma that originates in the EPITHELIUM of the NASOPHARYNX and includes four subtypes: keratinizing squamous cell, non-keratinizing, basaloid squamous cell, and PAPILLARY ADENOCARCINOMA. It is most prevalent in Southeast Asian populations and is associated with EPSTEIN-BARR VIRUS INFECTIONS. Somatic mutations associated with this cancer have been identified in NPCR, BAP1, UBAP1, ERBB2, ERBB3, MLL2, PIK3CA, KRAS, NRAS, and ARID1A genes.	2.15	1	0
Cancer of Nasopharynx [description not available]	2.15	1	0
Nasopharyngeal Neoplasms Tumors or cancer of the NASOPHARYNX.	2.15	1	0
Skin Aging The process of aging due to changes in the structure and elasticity of the skin over time. It may be a part of physiological aging or it may be due to the effects of ultraviolet radiation, usually through exposure to sunlight.	5.68	6	3
Psychoses [description not available]	2.48	2	0
Psychotic Disorders Disorders in which there is a loss of ego boundaries or a gross impairment in reality testing with delusions or prominent hallucinations. (From DSM-IV, 1994)	2.48	2	0
Osteogenic Sarcoma [description not available]	3.06	4	0
Osteosarcoma A sarcoma originating in bone-forming cells, affecting the ends of long bones. It is the most common and most malignant of sarcomas of the bones, and occurs chiefly among 10- to 25-year-old youths. (From Stedman, 25th ed)	3.06	4	0
Adenocarcinoma Of Kidney [description not available]	3.01	4	0
Cancer of Kidney [description not available]	4.23	6	0
Carcinoma, Renal Cell A heterogeneous group of sporadic or hereditary carcinoma derived from cells of the KIDNEYS. There are several subtypes including the clear cells, the papillary, the chromophobe, the collecting duct, the spindle cells (sarcomatoid), or mixed cell-type carcinoma.	3.01	4	0
Kidney Neoplasms Tumors or cancers of the KIDNEY.	4.23	6	0
Kaposi Sarcoma [description not available]	2.53	2	0
Sarcoma, Kaposi A multicentric, malignant neoplastic vascular proliferation characterized by the development of bluish-red cutaneous nodules, usually on the lower extremities, most often on the toes or feet, and slowly increasing in size and number and spreading to more proximal areas. The tumors have endothelium-lined channels and vascular spaces admixed with variably sized aggregates of spindle-shaped cells, and often remain confined to the skin and subcutaneous tissue, but widespread visceral involvement may occur. Kaposi's sarcoma occurs spontaneously in Jewish and Italian males in Europe and the United States. An aggressive variant in young children is endemic in some areas of Africa. A third form occurs in about 0.04% of kidney transplant patients. There is also a high incidence in AIDS patients. (From Dorland, 27th ed & Holland et al., Cancer Medicine, 3d ed, pp2105-7) HHV-8 is the suspected cause.	2.53	2	0
Brain Disorders [description not available]	2.51	2	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.	2.51	2	0
Adverse Drug Event [description not available]	3.71	3	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.	3.71	3	0
Anxiety Feelings or emotions of dread, apprehension, and impending disaster but not disabling as with ANXIETY DISORDERS.	3.95	12	0
Infections, Orthomyxoviridae [description not available]	7.93	44	1
Orthomyxoviridae Infections Virus diseases caused by the ORTHOMYXOVIRIDAE.	7.93	44	1
Cirrhosis [description not available]	2.15	1	0
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	2.15	1	0
Encephalopathy, Toxic [description not available]	2.98	4	0
Congenital Epulides [description not available]	2.15	1	0
Adenoma, Prostatic [description not available]	2.7	3	0
Prostatic Hyperplasia Increase in constituent cells in the PROSTATE, leading to enlargement of the organ (hypertrophy) and adverse impact on the lower urinary tract function. This can be caused by increased rate of cell proliferation, reduced rate of cell death, or both.	2.7	3	0
Weight Gain Increase in BODY WEIGHT over existing weight.	4.8	7	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)	5.8	34	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.	2.17	1	0
Avian Flu [description not available]	2.76	3	0
Influenza in Birds Infection of domestic and wild fowl and other BIRDS with INFLUENZA A VIRUS. Avian influenza usually does not sicken birds, but can be highly pathogenic and fatal in domestic POULTRY.	2.76	3	0
Bowel Diseases, Inflammatory [description not available]	3.74	3	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.	3.74	3	0
Insulin Sensitivity [description not available]	4.97	8	1
Leanness [description not available]	2.17	1	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.	4.97	8	1
Experimental Leukemia [description not available]	3.34	7	0
Granulocytic Leukemia, Chronic [description not available]	2.98	4	0
Leukemia, Myelogenous, Chronic, BCR-ABL Positive Clonal hematopoetic disorder caused by an acquired genetic defect in PLURIPOTENT STEM CELLS. It starts in MYELOID CELLS of the bone marrow, invades the blood and then other organs. The condition progresses from a stable, more indolent, chronic phase (LEUKEMIA, MYELOID, CHRONIC PHASE) lasting up to 7 years, to an advanced phase composed of an accelerated phase (LEUKEMIA, MYELOID, ACCELERATED PHASE) and BLAST CRISIS.	2.98	4	0
Retinal Pigment Epithelial Detachment [description not available]	2.38	2	0
Syndrome, VKH (Vogt Koyanagi Harada) [description not available]	2.17	1	0
Retinal Detachment Separation of the inner layers of the retina (neural retina) from the pigment epithelium. Retinal detachment occurs more commonly in men than in women, in eyes with degenerative myopia, in aging and in aphakia. It may occur after an uncomplicated cataract extraction, but it is seen more often if vitreous humor has been lost during surgery. (Dorland, 27th ed; Newell, Ophthalmology: Principles and Concepts, 7th ed, p310-12).	2.38	2	0
Uveomeningoencephalitic Syndrome A syndrome characterized by bilateral granulomatous UVEITIS with IRITIS and secondary GLAUCOMA, premature ALOPECIA, symmetrical VITILIGO, poliosis circumscripta (a strand of depigmented hair), HEARING DISORDERS, and meningeal signs (neck stiffness and headache). Examination of the cerebrospinal fluid reveals a pattern consistent with MENINGITIS, ASEPTIC. (Adams et al., Principles of Neurology, 6th ed, p748; Surv Ophthalmol 1995 Jan;39(4):265-292)	2.17	1	0
Break-Bone Fever [description not available]	2.53	2	0
Dengue An acute febrile disease transmitted by the bite of AEDES mosquitoes infected with DENGUE VIRUS. It is self-limiting and characterized by fever, myalgia, headache, and rash. SEVERE DENGUE is a more virulent form of dengue.	2.53	2	0
Hypertension, Essential [description not available]	2.17	1	0
Essential Hypertension Hypertension that occurs without known cause, or preexisting renal disease. Associated polymorphisms for a number of genes have been identified, including AGT, GNB3, and ECE1. OMIM: 145500	2.17	1	0
Aqueductal Stenosis [description not available]	2.17	1	0
B16 Melanoma [description not available]	3.81	11	0
Neoplasms, Squamous Cell Neoplasms of the SQUAMOUS EPITHELIAL CELLS. The concept does not refer to neoplasms located in tissue composed of squamous elements.	2.17	1	0
Actinic Keratosis [description not available]	2.17	1	0
Keratosis, Actinic White or pink lesions on the arms, hands, face, or scalp that arise from sun-induced DNA DAMAGE to KERATINOCYTES in exposed areas. They are considered precursor lesions to superficial SQUAMOUS CELL CARCINOMA.	2.17	1	0
Insect Bites [description not available]	2.96	4	0
Insect Bites and Stings Bites and stings inflicted by insects.	2.96	4	0
Affective Disorders [description not available]	2.21	1	0
Mood Disorders Those disorders that have a disturbance in mood as their predominant feature.	2.21	1	0
Blood Clot [description not available]	2.39	2	0
Thrombosis Formation and development of a thrombus or blood clot in the blood vessel.	2.39	2	0
Diffuse Large B-Cell Lymphoma [description not available]	3.25	6	0
Lymphoma, Large B-Cell, Diffuse Malignant lymphoma composed of large B lymphoid cells whose nuclear size can exceed normal macrophage nuclei, or more than twice the size of a normal lymphocyte. The pattern is predominantly diffuse. Most of these lymphomas represent the malignant counterpart of B-lymphocytes at midstage in the process of differentiation.	3.25	6	0
Fetal Death Death of the developing young in utero. BIRTH of a dead FETUS is STILLBIRTH.	2.17	1	0
Dementia Praecox [description not available]	2.99	4	0
Schizophrenia A severe emotional disorder of psychotic depth characteristically marked by a retreat from reality with delusion formation, HALLUCINATIONS, emotional disharmony, and regressive behavior.	2.99	4	0
Cerebromeningitis [description not available]	2.52	2	0
Bone Cancer [description not available]	3.23	5	0
Bone Neoplasms Tumors or cancer located in bone tissue or specific BONES.	3.23	5	0
Cancer of Head [description not available]	4.52	5	1
Head and Neck Neoplasms Soft tissue tumors or cancer arising from the mucosal surfaces of the LIP; oral cavity; PHARYNX; LARYNX; and cervical esophagus. Other sites included are the NOSE and PARANASAL SINUSES; SALIVARY GLANDS; THYROID GLAND and PARATHYROID GLANDS; and MELANOMA and non-melanoma skin cancers of the head and neck. (from Holland et al., Cancer Medicine, 4th ed, p1651)	4.52	5	1
Clinically Isolated CNS Demyelinating Syndrome [description not available]	2.39	2	0
Demyelinating Diseases Diseases characterized by loss or dysfunction of myelin in the central or peripheral nervous system.	2.39	2	0
Polyarthritis [description not available]	2.87	4	0
Arthritis Acute or chronic inflammation of JOINTS.	2.87	4	0
Hepatitis B Virus Infection [description not available]	3.09	5	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.	3.09	5	0
Chondrosarcoma A slowly growing malignant neoplasm derived from cartilage cells, occurring most frequently in pelvic bones or near the ends of long bones, in middle-aged and old people. Most chondrosarcomas arise de novo, but some may develop in a preexisting benign cartilaginous lesion or in patients with ENCHONDROMATOSIS. (Stedman, 25th ed)	2.7	3	0
Atherogenesis [description not available]	3.58	8	0
Atherosclerosis A thickening and loss of elasticity of the walls of ARTERIES that occurs with formation of ATHEROSCLEROTIC PLAQUES within the ARTERIAL INTIMA.	3.58	8	0
Idiopathic Parkinson Disease [description not available]	3.74	11	0
Symptom Cluster [description not available]	2.9	4	0
Parkinson Disease A progressive, degenerative neurologic disease characterized by a TREMOR that is maximal at rest, retropulsion (i.e. a tendency to fall backwards), rigidity, stooped posture, slowness of voluntary movements, and a masklike facial expression. Pathologic features include loss of melanin containing neurons in the substantia nigra and other pigmented nuclei of the brainstem. LEWY BODIES are present in the substantia nigra and locus coeruleus but may also be found in a related condition (LEWY BODY DISEASE, DIFFUSE) characterized by dementia in combination with varying degrees of parkinsonism. (Adams et al., Principles of Neurology, 6th ed, p1059, pp1067-75)	3.74	11	0
Syndrome A characteristic symptom complex.	2.9	4	0
Colitis Inflammation of the COLON section of the large intestine (INTESTINE, LARGE), usually with symptoms such as DIARRHEA (often with blood and mucus), ABDOMINAL PAIN, and FEVER.	2.55	2	0
Airflow Obstruction, Chronic [description not available]	3.42	2	0
Pulmonary Hypertension [description not available]	2.54	2	0
Hypertension, Pulmonary Increased VASCULAR RESISTANCE in the PULMONARY CIRCULATION, usually secondary to HEART DISEASES or LUNG DISEASES.	2.54	2	0
Pulmonary Disease, Chronic Obstructive A disease of chronic diffuse irreversible airflow obstruction. Subcategories of COPD include CHRONIC BRONCHITIS and PULMONARY EMPHYSEMA.	3.42	2	0
Convulsive Generalized Seizure Disorder [description not available]	3.12	1	0
Left Ventricular Hypertrophy [description not available]	2.52	2	0
Cardiac Failure [description not available]	2.52	2	0
Heart Failure A heterogeneous condition in which the heart is unable to pump out sufficient blood to meet the metabolic need of the body. Heart failure can be caused by structural defects, functional abnormalities (VENTRICULAR DYSFUNCTION), or a sudden overload beyond its capacity. Chronic heart failure is more common than acute heart failure which results from sudden insult to cardiac function, such as MYOCARDIAL INFARCTION.	2.52	2	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.	2.52	2	0
Acute Respiratory Distress Syndrome [description not available]	3.03	4	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.	3.03	4	0
Alcohol Drinking Behaviors associated with the ingesting of ALCOHOLIC BEVERAGES, including social drinking.	4.76	11	0
Experimental Spinal Cord Ischemia [description not available]	2.21	1	0
Laurence-Moon-Bardet-Biedl Syndrome [description not available]	2.21	1	0
Bardet-Biedl Syndrome An autosomal recessive disorder characterized by RETINITIS PIGMENTOSA; POLYDACTYLY; OBESITY; MENTAL RETARDATION; hypogenitalism; renal dysplasia; and short stature. This syndrome has been distinguished as a separate entity from LAURENCE-MOON SYNDROME. (From J Med Genet 1997 Feb;34(2):92-8)	2.21	1	0
Infections, Rhabdoviridae [description not available]	2.45	2	0
Atherosclerotic Parkinsonism [description not available]	2.72	3	0
Parkinson Disease, Secondary Conditions which feature clinical manifestations resembling primary Parkinson disease that are caused by a known or suspected condition. Examples include parkinsonism caused by vascular injury, drugs, trauma, toxin exposure, neoplasms, infections and degenerative or hereditary conditions. Clinical features may include bradykinesia, rigidity, parkinsonian gait, and masked facies. In general, tremor is less prominent in secondary parkinsonism than in the primary form. (From Joynt, Clinical Neurology, 1998, Ch38, pp39-42)	2.72	3	0
Hematologic Malignancies [description not available]	9.15	37	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.	9.15	37	0
Left Ventricular Dysfunction [description not available]	2.8	3	0
Ventricular Dysfunction, Left A condition in which the LEFT VENTRICLE of the heart was functionally impaired. This condition usually leads to HEART FAILURE; MYOCARDIAL INFARCTION; and other cardiovascular complications. Diagnosis is made by measuring the diminished ejection fraction and a depressed level of motility of the left ventricular wall.	2.8	3	0
Academic Disorder, Developmental [description not available]	2.08	1	0
Learning Disabilities Conditions characterized by a significant discrepancy between an individual's perceived level of intellect and their ability to acquire new language and other cognitive skills. These may result from organic or psychological conditions. Relatively common subtypes include DYSLEXIA, DYSCALCULIA, and DYSGRAPHIA.	2.08	1	0
Binge Alcohol Consumption [description not available]	2.1	1	0
Acute Onset Vascular Dementia [description not available]	2.08	1	0
Dementia, Vascular An imprecise term referring to dementia associated with CEREBROVASCULAR DISORDERS, including CEREBRAL INFARCTION (single or multiple), and conditions associated with chronic BRAIN ISCHEMIA. Diffuse, cortical, and subcortical subtypes have been described. (From Gerontol Geriatr 1998 Feb;31(1):36-44)	2.08	1	0
Ache [description not available]	7.92	17	3
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	12.92	17	3
Anterior Cerebral Circulation Infarction [description not available]	2.46	2	0
Brain Infarction Tissue NECROSIS in any area of the brain, including the CEREBRAL HEMISPHERES, the CEREBELLUM, and the BRAIN STEM. Brain infarction is the result of a cascade of events initiated by inadequate blood flow through the brain that is followed by HYPOXIA and HYPOGLYCEMIA in brain tissue. Damage may be temporary, permanent, selective or pan-necrosis.	2.46	2	0
Interstitial Cell Tumor [description not available]	2.43	2	0
Cancer of Testis [description not available]	3.77	2	1
Testicular Neoplasms Tumors or cancer of the TESTIS. Germ cell tumors (GERMINOMA) of the testis constitute 95% of all testicular neoplasms.	3.77	2	1
Muscle Relaxation That phase of a muscle twitch during which a muscle returns to a resting position.	3.5	8	0
Anoxemia [description not available]	4.67	10	0
Hypoxia Sub-optimal OXYGEN levels in the ambient air of living organisms.	4.67	10	0
Epithelial Neoplasms [description not available]	2.08	1	0
Infections, Lentivirus [description not available]	2.1	1	0
Blastocyst Disintegration [description not available]	2.1	1	0
Dermatitis, Contact, Photoallergic [description not available]	4.13	3	0
Dermatitis, Contact, Phototoxic [description not available]	3.87	2	0
Allergy, Drug [description not available]	4.77	5	0
Drug Hypersensitivity Immunologically mediated adverse reactions to medicinal substances used legally or illegally.	4.77	5	0
Injuries Used with anatomic headings, animals, and sports for wounds and injuries. Excludes cell damage, for which pathology is used.	5.42	23	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.	5.42	23	0
Recrudescence [description not available]	2.46	2	0
Breathlessness [description not available]	2.1	1	0
Carditis [description not available]	2.48	2	0
Pleuropericarditis Inflammation of both the PERICARDIUM and the PLEURA.	2.1	1	0
Dyspnea Difficult or labored breathing.	2.1	1	0
Myocarditis Inflammatory processes of the muscular walls of the heart (MYOCARDIUM) which result in injury to the cardiac muscle cells (MYOCYTES, CARDIAC). Manifestations range from subclinical to sudden death (DEATH, SUDDEN). Myocarditis in association with cardiac dysfunction is classified as inflammatory CARDIOMYOPATHY usually caused by INFECTION, autoimmune diseases, or responses to toxic substances. Myocarditis is also a common cause of DILATED CARDIOMYOPATHY and other cardiomyopathies.	2.48	2	0
Pericarditis Inflammation of the PERICARDIUM from various origins, such as infection, neoplasm, autoimmune process, injuries, or drug-induced. Pericarditis usually leads to PERICARDIAL EFFUSION, or CONSTRICTIVE PERICARDITIS.	2.1	1	0
Bladder Cancer [description not available]	2.78	3	0
Urinary Bladder Neoplasms Tumors or cancer of the URINARY BLADDER.	2.78	3	0
Pneumonia, Pneumococcal A febrile disease caused by STREPTOCOCCUS PNEUMONIAE.	3.3	2	0
Leucocythaemia [description not available]	3.27	6	0
Leukemia A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)	3.27	6	0
Histomoniasis [description not available]	2.1	1	0
Pyrexia [description not available]	2.72	3	0
Fever An abnormal elevation of body temperature, usually as a result of a pathologic process.	2.72	3	0
Cystic Fibrosis of Pancreas [description not available]	2.7	3	0
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.	2.7	3	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).	5.14	10	1
Infections, Trichomonas [description not available]	2.48	2	0
Trichomonas Infections Infections in birds and mammals produced by various species of Trichomonas.	2.48	2	0
Emesis [description not available]	4.28	4	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.	2.9	4	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.	3.84	2	1
Vomiting The forcible expulsion of the contents of the STOMACH through the MOUTH.	4.28	4	1
Akinetic-Rigid Variant of Huntington Disease [description not available]	2.1	1	0
Huntington Disease A familial disorder inherited as an autosomal dominant trait and characterized by the onset of progressive CHOREA and DEMENTIA in the fourth or fifth decade of life. Common initial manifestations include paranoia; poor impulse control; DEPRESSION; HALLUCINATIONS; and DELUSIONS. Eventually intellectual impairment; loss of fine motor control; ATHETOSIS; and diffuse chorea involving axial and limb musculature develops, leading to a vegetative state within 10-15 years of disease onset. The juvenile variant has a more fulminant course including SEIZURES; ATAXIA; dementia; and chorea. (From Adams et al., Principles of Neurology, 6th ed, pp1060-4)	2.1	1	0
Organophosphorus Poisoning [description not available]	4.81	5	0
Organophosphate Poisoning Poisoning due to exposure to ORGANOPHOSPHORUS COMPOUNDS, such as ORGANOPHOSPHATES; ORGANOTHIOPHOSPHATES; and ORGANOTHIOPHOSPHONATES.	4.81	5	0
Cholangiocellular Carcinoma [description not available]	2.1	1	0
Bile Duct Cancer [description not available]	2.1	1	0
Bile Duct Neoplasms Tumors or cancer of the BILE DUCTS.	2.1	1	0
Cholangiocarcinoma A malignant tumor arising from the epithelium of the BILE DUCTS.	2.1	1	0
B-Cell Leukemia [description not available]	2.1	1	0
Cardiovascular Stroke [description not available]	2.47	2	0
Myocardial Infarction NECROSIS of the MYOCARDIUM caused by an obstruction of the blood supply to the heart (CORONARY CIRCULATION).	2.47	2	0
Androgen-Independent Prostatic Cancer [description not available]	2.52	2	0
Prostatic Neoplasms, Castration-Resistant Tumors or cancer of the PROSTATE which can grow in the presence of low or residual amount of androgen hormones such as TESTOSTERONE.	2.52	2	0
Thrombopenia [description not available]	2.51	2	0
Thrombocytopenia A subnormal level of BLOOD PLATELETS.	2.51	2	0
Genome Instability [description not available]	2.49	2	0
Child Behavior Disorders Disturbances considered to be pathological based on age and stage appropriateness, e.g., conduct disturbances and anaclitic depression. This concept does not include psychoneuroses, psychoses, or personality disorders with fixed patterns.	2.11	1	0
Bacterial Pneumonia [description not available]	2.11	1	0
Acute Hypercapnic Respiratory Failure [description not available]	2.76	3	0
Microbial Superinvasion [description not available]	2.11	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)	2.76	3	0
Pneumonia, Bacterial Inflammation of the lung parenchyma that is caused by bacterial infections.	2.11	1	0
Cancer of the Urinary Tract [description not available]	2.11	1	0
Anti-MuSK Myasthenia Gravis [description not available]	2.11	1	0
Myasthenia Gravis A disorder of neuromuscular transmission characterized by fatigable weakness of cranial and skeletal muscles with elevated titers of ACETYLCHOLINE RECEPTORS or muscle-specific receptor tyrosine kinase (MuSK) autoantibodies. Clinical manifestations may include ocular muscle weakness (fluctuating, asymmetric, external ophthalmoplegia; diplopia; ptosis; and weakness of eye closure) and extraocular fatigable weakness of facial, bulbar, respiratory, and proximal limb muscles. The disease may remain limited to the ocular muscles (ocular myasthenia). THYMOMA is commonly associated with this condition.	2.11	1	0
Swine Diseases Diseases of domestic swine and of the wild boar of the genus Sus.	2.48	2	0
Corpus Luteum Cyst [description not available]	2.52	2	0
Ovarian Cysts General term for CYSTS and cystic diseases of the OVARY.	2.52	2	0
MODS [description not available]	4.41	1	1
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.	4.41	1	1
Infections, Pneumococcal [description not available]	2.66	3	0
Pneumococcal Infections Infections with bacteria of the species STREPTOCOCCUS PNEUMONIAE.	2.66	3	0
Chronic Lung Injury [description not available]	2.11	1	0
Injury, Myocardial Reperfusion [description not available]	2.96	4	0
Adrenocortical Carcinoma A malignant neoplasm of the ADRENAL CORTEX. Adrenocortical carcinomas are unencapsulated anaplastic (ANAPLASIA) masses sometimes exceeding 20 cm or 200 g. They are more likely to be functional than nonfunctional, and produce ADRENAL CORTEX HORMONES that may result in hypercortisolism (CUSHING SYNDROME); HYPERALDOSTERONISM; and/or VIRILISM.	2.11	1	0
Adrenal Cortex Cancer [description not available]	2.11	1	0
Adrenal Cortex Neoplasms Tumors or cancers of the ADRENAL CORTEX.	2.11	1	0
Vitiligo A disorder consisting of areas of macular depigmentation, commonly on extensor aspects of extremities, on the face or neck, and in skin folds. Age of onset is often in young adulthood and the condition tends to progress gradually with lesions enlarging and extending until a quiescent state is reached.	2.42	2	0
Fibrosarcoma A sarcoma derived from deep fibrous tissue, characterized by bundles of immature proliferating fibroblasts with variable collagen formation, which tends to invade locally and metastasize by the bloodstream. (Stedman, 25th ed)	3.99	5	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.	2.15	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.	2.15	1	0
Carcinoma, Transitional Cell A malignant neoplasm derived from TRANSITIONAL EPITHELIAL CELLS, occurring chiefly in the URINARY BLADDER; URETERS; or RENAL PELVIS.	2.11	1	0
Central Nervous System Disease [description not available]	2.13	1	0
Central Nervous System Diseases Diseases of any component of the brain (including the cerebral hemispheres, diencephalon, brain stem, and cerebellum) or the spinal cord.	2.13	1	0
Diffuse Lymphocytic Lymphoma, Poorly-Differentiated [description not available]	2.13	1	0
Lymphoma, Mantle-Cell A form of non-Hodgkin lymphoma having a usually diffuse pattern with both small and medium lymphocytes and small cleaved cells. It accounts for about 5% of adult non-Hodgkin lymphomas in the United States and Europe. The majority of mantle-cell lymphomas are associated with a t(11;14) translocation resulting in overexpression of the CYCLIN D1 gene (GENES, BCL-1).	2.13	1	0
Aura [description not available]	3.83	4	0
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)	3.83	4	0
Dyskinesia, Medication-Induced [description not available]	2.13	1	0
Dyskinesia, Drug-Induced Abnormal movements, including HYPERKINESIS; HYPOKINESIA; TREMOR; and DYSTONIA, associated with the use of certain medications or drugs. Muscles of the face, trunk, neck, and extremities are most commonly affected. Tardive dyskinesia refers to abnormal hyperkinetic movements of the muscles of the face, tongue, and neck associated with the use of neuroleptic agents (see ANTIPSYCHOTIC AGENTS). (Adams et al., Principles of Neurology, 6th ed, p1199)	2.13	1	0
DNA Virus Infections Diseases caused by DNA VIRUSES.	2.45	2	0
Pulmonary Arterial Remodeling [description not available]	2.13	1	0
Parasitemia The presence of parasites (especially malarial parasites) in the blood. (Dorland, 27th ed)	2.11	1	0
Infections, Plasmodium [description not available]	2.87	4	0
Malaria A protozoan disease caused in humans by four species of the PLASMODIUM genus: PLASMODIUM FALCIPARUM; PLASMODIUM VIVAX; PLASMODIUM OVALE; and PLASMODIUM MALARIAE; and transmitted by the bite of an infected female mosquito of the genus ANOPHELES. Malaria is endemic in parts of Asia, Africa, Central and South America, Oceania, and certain Caribbean islands. It is characterized by extreme exhaustion associated with paroxysms of high FEVER; SWEATING; shaking CHILLS; and ANEMIA. Malaria in ANIMALS is caused by other species of plasmodia.	2.87	4	0
Impaired Glucose Tolerance [description not available]	2.5	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.	2.5	2	0
Leukemia, Lymphoblastic, Acute, T Cell [description not available]	2.13	1	0
Precursor T-Cell Lymphoblastic Leukemia-Lymphoma A leukemia/lymphoma found predominately in children and young adults and characterized LYMPHADENOPATHY and THYMUS GLAND involvement. It most frequently presents as a lymphoma, but a leukemic progression in the bone marrow is common.	2.13	1	0
Erythrophagocytic Lymphohistiocytosis, Familial [description not available]	2.13	1	0
Lymphohistiocytosis, Hemophagocytic A group of related disorders characterized by LYMPHOCYTOSIS; HISTIOCYTOSIS; and hemophagocytosis. The two major forms are familial and reactive.	2.13	1	0
Liver Steatosis [description not available]	2.13	1	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.	2.13	1	0
Bronchial Pneumonia [description not available]	2.13	1	0
Injuries, Spinal Cord [description not available]	2.77	3	0
Spinal Cord Injuries Penetrating and non-penetrating injuries to the spinal cord resulting from traumatic external forces (e.g., WOUNDS, GUNSHOT; WHIPLASH INJURIES; etc.).	2.77	3	0
Cognition Disorders Disorders characterized by disturbances in mental processes related to learning, thinking, reasoning, and judgment.	4.54	5	1
Graft-Versus-Host Disease [description not available]	2.54	2	0
Graft vs Host Disease The clinical entity characterized by anorexia, diarrhea, loss of hair, leukopenia, thrombocytopenia, growth retardation, and eventual death brought about by the GRAFT VS HOST REACTION.	2.54	2	0
Herpes Simplex Virus Infection [description not available]	2.9	4	0
Herpes Simplex A group of acute infections caused by herpes simplex virus type 1 or type 2 that is characterized by the development of one or more small fluid-filled vesicles with a raised erythematous base on the skin or mucous membrane. It occurs as a primary infection or recurs due to a reactivation of a latent infection. (Dorland, 27th ed.)	2.9	4	0
Acute Lymphoid Leukemia [description not available]	2.5	2	0
Precursor Cell Lymphoblastic Leukemia-Lymphoma A neoplasm characterized by abnormalities of the lymphoid cell precursors leading to excessive lymphoblasts in the marrow and other organs. It is the most common cancer in children and accounts for the vast majority of all childhood leukemias.	2.5	2	0
Community Acquired Infection [description not available]	2.15	1	0
Health Care Associated Infection [description not available]	2.15	1	0
Cross Infection Any infection which a patient contracts in a health-care institution.	2.15	1	0
Carcinoma, Colloid [description not available]	2.15	1	0
Adenocarcinoma, Mucinous An adenocarcinoma producing mucin in significant amounts. (From Dorland, 27th ed)	2.15	1	0
Sclerosis, Systemic [description not available]	2.15	1	0
B-Cell Lymphoma [description not available]	3.1	5	0
Scleroderma, Systemic A chronic multi-system disorder of CONNECTIVE TISSUE. It is characterized by SCLEROSIS in the SKIN, the LUNGS, the HEART, the GASTROINTESTINAL TRACT, the KIDNEYS, and the MUSCULOSKELETAL SYSTEM. Other important features include diseased small BLOOD VESSELS and AUTOANTIBODIES. The disorder is named for its most prominent feature (hard skin), and classified into subsets by the extent of skin thickening: LIMITED SCLERODERMA and DIFFUSE SCLERODERMA.	2.15	1	0
Lymphoma, B-Cell A group of heterogeneous lymphoid tumors generally expressing one or more B-cell antigens or representing malignant transformations of B-lymphocytes.	3.1	5	0
Gastric Ulcer [description not available]	3.23	6	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).	3.23	6	0
Infections, Paramyxoviridae [description not available]	3.06	1	0
Infections, Respiratory Syncytial Virus [description not available]	3.06	1	0
Infections, Picornaviridae [description not available]	3.06	1	0
Infections, Respiratory [description not available]	3.06	1	0
Respiratory Tract Infections Invasion of the host RESPIRATORY SYSTEM by microorganisms, usually leading to pathological processes or diseases.	3.06	1	0
Paramyxoviridae Infections Infections with viruses of the family PARAMYXOVIRIDAE. This includes MORBILLIVIRUS INFECTIONS; RESPIROVIRUS INFECTIONS; PNEUMOVIRUS INFECTIONS; HENIPAVIRUS INFECTIONS; AVULAVIRUS INFECTIONS; and RUBULAVIRUS INFECTIONS.	3.06	1	0
Respiratory Syncytial Virus Infections Pneumovirus infections caused by the RESPIRATORY SYNCYTIAL VIRUSES. Humans and cattle are most affected but infections in goats and sheep have been reported.	3.06	1	0
Visceral Pain Pain originating from internal organs (VISCERA) associated with autonomic phenomena (PALLOR; SWEATING; NAUSEA; and VOMITING). It often becomes a REFERRED PAIN.	2.15	1	0
Addiction, Opioid [description not available]	3.04	5	0
Opioid-Related Disorders Disorders related to or resulting from abuse or misuse of OPIOIDS.	3.04	5	0
Hyperactivity, Motor [description not available]	2.94	4	0
Autosomal Dominant Juvenile Parkinson Disease [description not available]	4.13	17	0
Anochlesia [description not available]	3.51	8	0
Parkinsonian Disorders A group of disorders which feature impaired motor control characterized by bradykinesia, MUSCLE RIGIDITY; TREMOR; and postural instability. Parkinsonian diseases are generally divided into primary parkinsonism (see PARKINSON DISEASE), secondary parkinsonism (see PARKINSON DISEASE, SECONDARY) and inherited forms. These conditions are associated with dysfunction of dopaminergic or closely related motor integration neuronal pathways in the BASAL GANGLIA.	4.13	17	0
Gas Poisoning Poisoning that results from exposure to gases such as CARBON MONOXIDE; NOBLE GASES; OXYGEN; or NATURAL GAS.	2.96	1	0
Labor, Premature [description not available]	2.05	1	0
Endometrial Diseases [description not available]	2.05	1	0
Uterine Diseases Pathological processes involving any part of the UTERUS.	2.05	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.	3.77	2	1
Sclerosis A pathological process consisting of hardening or fibrosis of an anatomical structure, often a vessel or a nerve.	1.92	1	0
Action Tremor [description not available]	2.64	3	0
Tremor Cyclical movement of a body part that can represent either a physiologic process or a manifestation of disease. Intention or action tremor, a common manifestation of CEREBELLAR DISEASES, is aggravated by movement. In contrast, resting tremor is maximal when there is no attempt at voluntary movement, and occurs as a relatively frequent manifestation of PARKINSON DISEASE.	2.64	3	0
Basal Ganglia Diseases Diseases of the BASAL GANGLIA including the PUTAMEN; GLOBUS PALLIDUS; claustrum; AMYGDALA; and CAUDATE NUCLEUS. DYSKINESIAS (most notably involuntary movements and alterations of the rate of movement) represent the primary clinical manifestations of these disorders. Common etiologies include CEREBROVASCULAR DISORDERS; NEURODEGENERATIVE DISEASES; and CRANIOCEREBRAL TRAUMA.	3.18	6	0
Torsade de Pointes [description not available]	2.04	1	0
Abnormalities, Autosome [description not available]	2.05	1	0
Adenocarcinoma, Clear Cell An adenocarcinoma characterized by the presence of varying combinations of clear and hobnail-shaped tumor cells. There are three predominant patterns described as tubulocystic, solid, and papillary. These tumors, usually located in the female reproductive organs, have been seen more frequently in young women since 1970 as a result of the association with intrauterine exposure to diethylstilbestrol. (From Holland et al., Cancer Medicine, 3d ed)	2.05	1	0
Alloxan Diabetes [description not available]	3.37	7	0
Asymmetric Diabetic Proximal Motor Neuropathy [description not available]	2.05	1	0
Diabetic Neuropathies Peripheral, autonomic, and cranial nerve disorders that are associated with DIABETES MELLITUS. These conditions usually result from diabetic microvascular injury involving small blood vessels that supply nerves (VASA NERVORUM). Relatively common conditions which may be associated with diabetic neuropathy include third nerve palsy (see OCULOMOTOR NERVE DISEASES); MONONEUROPATHY; mononeuropathy multiplex; diabetic amyotrophy; a painful POLYNEUROPATHY; autonomic neuropathy; and thoracoabdominal neuropathy. (From Adams et al., Principles of Neurology, 6th ed, p1325)	2.05	1	0
Granulocytic Leukemia [description not available]	2.7	3	0
Leukemia, Myeloid Form of leukemia characterized by an uncontrolled proliferation of the myeloid lineage and their precursors (MYELOID PROGENITOR CELLS) in the bone marrow and other sites.	2.7	3	0
Bradykinesia [description not available]	2.05	1	0
Catatonic Rigidity [description not available]	2.05	1	0
Muscle Rigidity Continuous involuntary sustained muscle contraction which is often a manifestation of BASAL GANGLIA DISEASES. When an affected muscle is passively stretched, the degree of resistance remains constant regardless of the rate at which the muscle is stretched. This feature helps to distinguish rigidity from MUSCLE SPASTICITY. (From Adams et al., Principles of Neurology, 6th ed, p73)	2.05	1	0
Angioma A vascular anomaly due to proliferation of blood or lymphatic vessels that forms a tumor-like mass. Vessels in the angioma may or may not be dilated.	2.05	1	0
Hemangioma A vascular anomaly due to proliferation of BLOOD VESSELS that forms a tumor-like mass. The common types involve CAPILLARIES and VEINS. It can occur anywhere in the body but is most frequently noticed in the SKIN and SUBCUTANEOUS TISSUE. (from Stedman, 27th ed, 2000)	2.05	1	0
Morphine Abuse [description not available]	2.42	2	0
Drug Withdrawal Symptoms [description not available]	3.26	6	0
Morphine Dependence Strong dependence, both physiological and emotional, upon morphine.	2.42	2	0
Substance Withdrawal Syndrome Physiological and psychological symptoms associated with withdrawal from the use of a drug after prolonged administration or habituation. The concept includes withdrawal from smoking or drinking, as well as withdrawal from an administered drug.	3.26	6	0
Chronic Insomnia [description not available]	4.41	2	2
Sleep Initiation and Maintenance Disorders Disorders characterized by impairment of the ability to initiate or maintain sleep. This may occur as a primary disorder or in association with another medical or psychiatric condition.	4.41	2	2
A-alphalipoprotein Neuropathy [description not available]	2.42	2	0
Emergencies Situations or conditions requiring immediate intervention to avoid serious adverse results.	4.36	4	0
Chromosome-Defective Micronuclei [description not available]	2.43	2	0
Ectoparasitic Infestations Infestations by PARASITES which live on, or burrow into, the surface of their host's EPIDERMIS. Most ectoparasites are ARTHROPODS.	2.05	1	0
Dyskinesia Syndromes [description not available]	2.64	3	0
Movement Disorders Syndromes which feature DYSKINESIAS as a cardinal manifestation of the disease process. Included in this category are degenerative, hereditary, post-infectious, medication-induced, post-inflammatory, and post-traumatic conditions.	2.64	3	0
Infectious Diseases [description not available]	2.86	4	0
Communicable Diseases An illness caused by an infectious agent or its toxins that occurs through the direct or indirect transmission of the infectious agent or its products from an infected individual or via an animal, vector or the inanimate environment to a susceptible animal or human host.	2.86	4	0
Acquired Autoimmune Hemolytic Anemia [description not available]	2.05	1	0
Anemia, Hemolytic, Autoimmune Acquired hemolytic anemia due to the presence of AUTOANTIBODIES which agglutinate or lyse the patient's own RED BLOOD CELLS.	2.05	1	0
Weight Reduction [description not available]	2.05	1	0
Weight Loss Decrease in existing BODY WEIGHT.	2.05	1	0
Diabetic Glomerulosclerosis [description not available]	2.05	1	0
Diabetic Nephropathies KIDNEY injuries associated with diabetes mellitus and affecting KIDNEY GLOMERULUS; ARTERIOLES; KIDNEY TUBULES; and the interstitium. Clinical signs include persistent PROTEINURIA, from microalbuminuria progressing to ALBUMINURIA of greater than 300 mg/24 h, leading to reduced GLOMERULAR FILTRATION RATE and END-STAGE RENAL DISEASE.	2.05	1	0
Cocaine Abuse [description not available]	2.96	4	0
Cocaine-Related Disorders Disorders related or resulting from use of cocaine.	2.96	4	0
Rodent Diseases Diseases of rodents of the order RODENTIA. This term includes diseases of Sciuridae (squirrels), Geomyidae (gophers), Heteromyidae (pouched mice), Castoridae (beavers), Cricetidae (rats and mice), Muridae (Old World rats and mice), Erethizontidae (porcupines), and Caviidae (guinea pigs).	2.38	2	0
Psychoses, Drug [description not available]	2.38	2	0
Cancer of Colon [description not available]	5.46	15	1
Colonic Neoplasms Tumors or cancer of the COLON.	5.46	15	1
Leukokeratosis Leukoplakic lesions related to abnormal keratin fiber formation.	2.06	1	0
Condition, Preneoplastic [description not available]	2.72	3	0
Lentigines [description not available]	2.06	1	0
Lentigo Small circumscribed melanoses resembling, but differing histologically from, freckles. The concept includes senile lentigo ('liver spots') and nevoid lentigo (nevus spilus, lentigo simplex) and may also occur in association with multiple congenital defects or congenital syndromes (e.g., Peutz-Jeghers syndrome).	2.06	1	0
Leukoplakia A white patch lesion found on a MUCOUS MEMBRANE that cannot be scraped off. Leukoplakia is generally considered a precancerous condition, however its appearance may also result from a variety of HEREDITARY DISEASES.	2.06	1	0
Precancerous Conditions Pathological conditions that tend eventually to become malignant.	2.72	3	0
Lichen Planus, Oral Oral lesions accompanying cutaneous lichen planus or often occurring alone. The buccal mucosa, lips, gingivae, floor of the mouth, and palate are usually affected (in a descending order of frequency). Typically, oral lesions consist of radiating white or gray, velvety, threadlike lines, arranged in a reticular pattern, at the intersection of which there may be minute, white, elevated dots or streaks (Wickham's striae). (Jablonski, Illustrated Dictionary of Dentistry)	2.06	1	0
Fra(X) Syndrome [description not available]	2.06	1	0
Audiogenic Epilepsy [description not available]	2.71	3	0
Fragile X Syndrome A condition characterized genotypically by mutation of the distal end of the long arm of the X chromosome (at gene loci FRAXA or FRAXE) and phenotypically by cognitive impairment, hyperactivity, SEIZURES, language delay, and enlargement of the ears, head, and testes. INTELLECTUAL DISABILITY occurs in nearly all males and roughly 50% of females with the full mutation of FRAXA. (From Menkes, Textbook of Child Neurology, 5th ed, p226)	2.06	1	0
Epilepsy, Reflex A subtype of epilepsy characterized by seizures that are consistently provoked by a certain specific stimulus. Auditory, visual, and somatosensory stimuli as well as the acts of writing, reading, eating, and decision making are examples of events or activities that may induce seizure activity in affected individuals. (From Neurol Clin 1994 Feb;12(1):57-8)	2.71	3	0
Complications, Infectious Pregnancy [description not available]	2.06	1	0
Proteinuria The presence of proteins in the urine, an indicator of KIDNEY DISEASES.	2.92	4	0
Candida Infection [description not available]	2.38	2	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)	2.38	2	0
Di Guglielmo Disease [description not available]	3.24	6	0
Enlarged Spleen [description not available]	2.06	1	0
Leukemia, Erythroblastic, Acute A myeloproliferative disorder characterized by neoplastic proliferation of erythroblastic and myeloblastic elements with atypical erythroblasts and myeloblasts in the peripheral blood.	3.24	6	0
Poisoning Used with drugs, chemicals, and industrial materials for human or animal poisoning, acute or chronic, whether the poisoning is accidental, occupational, suicidal, by medication error, or by environmental exposure.	3.97	5	0
Inadequate Sleep [description not available]	2.06	1	0
Abnormalities, Multiple Congenital abnormalities that affect more than one organ or body structure.	2.07	1	0
Aneuploid [description not available]	2.07	1	0
Mucorales Infection [description not available]	2.06	1	0
Mucormycosis Infection in humans and animals caused by any fungus in the order MUCORALES (e.g., RHIZOPUS; MUCOR; CUNNINGHAMELLA; APOPHYSOMYCES; ABSIDIA; SAKSENAEA and RHIZOMUCOR) There are many clinical types associated with infection including central nervous system, lung, gastrointestinal tract, skin, orbit and paranasal sinuses. In humans, it usually occurs as an OPPORTUNISTIC INFECTION.	2.06	1	0
Anemia, Fanconi [description not available]	2.07	1	0
Fanconi Anemia Congenital disorder affecting all bone marrow elements, resulting in ANEMIA; LEUKOPENIA; and THROMBOPENIA, and associated with cardiac, renal, and limb malformations as well as dermal pigmentary changes. Spontaneous CHROMOSOME BREAKAGE is a feature of this disease along with predisposition to LEUKEMIA. There are at least 7 complementation groups in Fanconi anemia: FANCA, FANCB, FANCC, FANCD1, FANCD2, FANCE, FANCF, FANCG, and FANCL. (from Online Mendelian Inheritance in Man, http://www.ncbi.nlm.nih.gov/entrez/dispomim.cgi?id=227650, August 20, 2004)	2.07	1	0
Aggression Behavior which may be manifested by destructive and attacking action which is verbal or physical, by covert attitudes of hostility or by obstructionism.	2.89	4	0
Equine Diseases [description not available]	3.86	2	1
Compensatory Hyperinsulinemia A GLUCOSE-induced HYPERINSULINEMIA, a marker of insulin-resistant state. It is a mechanism to compensate for reduced sensitivity to insulin.	2.07	1	0
Hyperinsulinism A syndrome with excessively high INSULIN levels in the BLOOD. It may cause HYPOGLYCEMIA. Etiology of hyperinsulinism varies, including hypersecretion of a beta cell tumor (INSULINOMA); autoantibodies against insulin (INSULIN ANTIBODIES); defective insulin receptor (INSULIN RESISTANCE); or overuse of exogenous insulin or HYPOGLYCEMIC AGENTS.	2.07	1	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.	2.45	2	0
Ewing Sarcoma [description not available]	2.08	1	0
Sarcoma, Ewing A malignant tumor of the bone which always arises in the medullary tissue, occurring more often in cylindrical bones. The tumor occurs usually before the age of 20, about twice as frequently in males as in females.	2.08	1	0
Nerve Pain [description not available]	2.45	2	0
Neuralgia Intense or aching pain that occurs along the course or distribution of a peripheral or cranial nerve.	2.45	2	0
Nociceptive Pain Dull or sharp aching pain caused by stimulated NOCICEPTORS due to tissue injury, inflammation or diseases. It can be divided into somatic or tissue pain and VISCERAL PAIN.	2.07	1	0
Fibroid [description not available]	2.08	1	0
Cancer of the Uterus [description not available]	2.08	1	0
Leiomyoma A benign tumor derived from smooth muscle tissue, also known as a fibroid tumor. They rarely occur outside of the UTERUS and the GASTROINTESTINAL TRACT but can occur in the SKIN and SUBCUTANEOUS TISSUE, probably arising from the smooth muscle of small blood vessels in these tissues.	2.08	1	0
Uterine Neoplasms Tumors or cancer of the UTERUS.	2.08	1	0
Convulsions, Grand Mal [description not available]	2.68	3	0
Epilepsy, Tonic-Clonic A generalized seizure disorder characterized by recurrent major motor seizures. The initial brief tonic phase is marked by trunk flexion followed by diffuse extension of the trunk and extremities. The clonic phase features rhythmic flexor contractions of the trunk and limbs, pupillary dilation, elevations of blood pressure and pulse, urinary incontinence, and tongue biting. This is followed by a profound state of depressed consciousness (post-ictal state) which gradually improves over minutes to hours. The disorder may be cryptogenic, familial, or symptomatic (caused by an identified disease process). (From Adams et al., Principles of Neurology, 6th ed, p329)	2.68	3	0
Bradyarrhythmia [description not available]	2.08	1	0
Bradycardia Cardiac arrhythmias that are characterized by excessively slow HEART RATE, usually below 50 beats per minute in human adults. They can be classified broadly into SINOATRIAL NODE dysfunction and ATRIOVENTRICULAR BLOCK.	2.08	1	0
Anoxia-Ischemia, Brain [description not available]	2.08	1	0
Hypoxia-Ischemia, Brain A disorder characterized by a reduction of oxygen in the blood combined with reduced blood flow (ISCHEMIA) to the brain from a localized obstruction of a cerebral artery or from systemic hypoperfusion. Prolonged hypoxia-ischemia is associated with ISCHEMIC ATTACK, TRANSIENT; BRAIN INFARCTION; BRAIN EDEMA; COMA; and other conditions.	2.08	1	0
HIV Human immunodeficiency virus. A non-taxonomic and historical term referring to any of two species, specifically HIV-1 and/or HIV-2. Prior to 1986, this was called human T-lymphotropic virus type III/lymphadenopathy-associated virus (HTLV-III/LAV). From 1986-1990, it was an official species called HIV. Since 1991, HIV was no longer considered an official species name; the two species were designated HIV-1 and HIV-2.	2.42	2	0
Carcinoma, Lewis Lung A carcinoma discovered by Dr. Margaret R. Lewis of the Wistar Institute in 1951. This tumor originated spontaneously as a carcinoma of the lung of a C57BL mouse. The tumor does not appear to be grossly hemorrhagic and the majority of the tumor tissue is a semifirm homogeneous mass. (From Cancer Chemother Rep 2 1972 Nov;(3)1:325) It is also called 3LL and LLC and is used as a transplantable malignancy.	2.01	1	0
Anoxia, Brain [description not available]	4.07	3	1
Brain Vascular Disorders [description not available]	2.92	1	0
Cerebrovascular Disorders A spectrum of pathological conditions of impaired blood flow in the brain. They can involve vessels (ARTERIES or VEINS) in the CEREBRUM, the CEREBELLUM, and the BRAIN STEM. Major categories include INTRACRANIAL ARTERIOVENOUS MALFORMATIONS; BRAIN ISCHEMIA; CEREBRAL HEMORRHAGE; and others.	2.92	1	0
Cancer of the Vulva [description not available]	2.01	1	0
Vulvar Neoplasms Tumors or cancer of the VULVA.	2.01	1	0
Leukemia, Lymphocytic [description not available]	2.88	4	0
Leukemia, Lymphoid Leukemia associated with HYPERPLASIA of the lymphoid tissues and increased numbers of circulating malignant LYMPHOCYTES and lymphoblasts.	2.88	4	0
Fasting Hypoglycemia HYPOGLYCEMIA expressed in the postabsorptive state, after prolonged FASTING, or an overnight fast.	3.21	6	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.	3.21	6	0
Axonotmesis [description not available]	2.01	1	0
Trauma, Nervous System Traumatic injuries to the brain, cranial nerves, spinal cord, autonomic nervous system, or neuromuscular system, including iatrogenic injuries induced by surgical procedures.	2.01	1	0
Histoplasma capsulatum Infection [description not available]	2.62	3	0
Histoplasmosis Infection resulting from exposure to the fungus HISTOPLASMA. It is worldwide in distribution and particularly common in the central and eastern states, especially areas around the Ohio and Mississippi River valleys.	2.62	3	0
Cancer, Second Primary [description not available]	1.93	1	0
Koch's Disease [description not available]	4.01	3	1
Tuberculosis Any of the infectious diseases of man and other animals caused by species of MYCOBACTERIUM TUBERCULOSIS.	4.01	3	1
Bronchospasm [description not available]	1.93	1	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.	2.33	2	0
Muscle Spasm [description not available]	2.33	2	0
Bronchial Diseases Diseases involving the BRONCHI.	1.93	1	0
Bronchial Spasm Spasmodic contraction of the smooth muscle of the bronchi.	1.93	1	0
Spasm An involuntary contraction of a muscle or group of muscles. Spasms may involve SKELETAL MUSCLE or SMOOTH MUSCLE.	2.33	2	0
Cardiac Murmurs [description not available]	1.93	1	0
Fungal Lung Diseases [description not available]	1.93	1	0
Dysesthesia [description not available]	1.93	1	0
Complications, Pregnancy [description not available]	1.93	1	0
Contact Dermatitis [description not available]	2.35	2	0
Dermatitis, Contact A type of acute or chronic skin reaction in which sensitivity is manifested by reactivity to materials or substances coming in contact with the skin. It may involve allergic or non-allergic mechanisms.	2.35	2	0
Hansen Disease [description not available]	2.34	2	0
Leprosy A chronic granulomatous infection caused by MYCOBACTERIUM LEPRAE. The granulomatous lesions are manifested in the skin, the mucous membranes, and the peripheral nerves. Two polar or principal types are lepromatous and tuberculoid.	2.34	2	0
Hepatitis, Infectious [description not available]	1.93	1	0
Hepatitis INFLAMMATION of the LIVER.	1.93	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.	1.93	1	0
Neoplasms, Pleural [description not available]	1.93	1	0
Pulmonary Consumption [description not available]	1.93	1	0
Tuberculosis, Pulmonary MYCOBACTERIUM infections of the lung.	1.93	1	0
Carcinoma 256, Walker A transplantable carcinoma of the rat that originally appeared spontaneously in the mammary gland of a pregnant albino rat, and which now resembles a carcinoma in young transplants and a sarcoma in older transplants. (Stedman, 25th ed)	3.04	5	0
Diffuse Mixed Small and Large Cell Lymphoma [description not available]	1.94	1	0
EHS Tumor [description not available]	3.04	5	0
Lymphoma, Non-Hodgkin Any of a group of malignant tumors of lymphoid tissue that differ from HODGKIN DISEASE, being more heterogeneous with respect to malignant cell lineage, clinical course, prognosis, and therapy. The only common feature among these tumors is the absence of giant REED-STERNBERG CELLS, a characteristic of Hodgkin's disease.	1.94	1	0
Atrophy Decrease in the size of a cell, tissue, organ, or multiple organs, associated with a variety of pathological conditions such as abnormal cellular changes, ischemia, malnutrition, or hormonal changes.	2.67	3	0
Coronary Restenosis Recurrent narrowing or constriction of a coronary artery following surgical procedures performed to alleviate a prior obstruction.	2.01	1	0
Neoplasms, Nervous System [description not available]	2.01	1	0
Brain Inflammation [description not available]	2.84	4	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.	2.84	4	0
Cerebral Palsy, Athetoid [description not available]	2.33	2	0
Cerebral Palsy A heterogeneous group of nonprogressive motor disorders caused by chronic brain injuries that originate in the prenatal period, perinatal period, or first few years of life. The four major subtypes are spastic, athetoid, ataxic, and mixed cerebral palsy, with spastic forms being the most common. The motor disorder may range from difficulties with fine motor control to severe spasticity (see MUSCLE SPASTICITY) in all limbs. Spastic diplegia (Little disease) is the most common subtype, and is characterized by spasticity that is more prominent in the legs than in the arms. Pathologically, this condition may be associated with LEUKOMALACIA, PERIVENTRICULAR. (From Dev Med Child Neurol 1998 Aug;40(8):520-7)	2.33	2	0
Basophilic Leukemia, Acute [description not available]	2.69	3	0
Leukemia, Basophilic, Acute A rare acute myeloid leukemia in which the primary differentiation is to BASOPHILS. It is characterized by an extreme increase of immature basophilic granulated cells in the bone marrow and blood. Mature basophils are usually sparse.	2.69	3	0
Ganglion Cysts Nodular tumor-like lesions or mucoid flesh, arising from tendon sheaths, LIGAMENTS, or JOINT CAPSULE, especially of the hands, wrists, or feet. They are not true cysts as they lack epithelial wall. They are distinguished from SYNOVIAL CYSTS by the lack of communication with a joint cavity or the SYNOVIAL MEMBRANE.	1.92	1	0
Clasp-Knife Spasticity [description not available]	2.33	2	0
Palsy [description not available]	2.62	3	0
Muscle Spasticity A form of muscle hypertonia associated with upper MOTOR NEURON DISEASE. Resistance to passive stretch of a spastic muscle results in minimal initial resistance (a free interval) followed by an incremental increase in muscle tone. Tone increases in proportion to the velocity of stretch. Spasticity is usually accompanied by HYPERREFLEXIA and variable degrees of MUSCLE WEAKNESS. (From Adams et al., Principles of Neurology, 6th ed, p54)	2.33	2	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)	2.62	3	0
Arrhythmia [description not available]	2.64	3	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.	2.64	3	0
Ventricular Fibrillation A potentially lethal cardiac arrhythmia that is characterized by uncoordinated extremely rapid firing of electrical impulses (400-600/min) in HEART VENTRICLES. Such asynchronous ventricular quivering or fibrillation prevents any effective cardiac output and results in unconsciousness (SYNCOPE). It is one of the major electrocardiographic patterns seen with CARDIAC ARREST.	1.92	1	0
Leukemia L 1210 [description not available]	3.91	13	0
Blood Poisoning [description not available]	3.33	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.	3.33	2	0
Nerve Degeneration Loss of functional activity and trophic degeneration of nerve axons and their terminal arborizations following the destruction of their cells of origin or interruption of their continuity with these cells. The pathology is characteristic of neurodegenerative diseases. Often the process of nerve degeneration is studied in research on neuroanatomical localization and correlation of the neurophysiology of neural pathways.	4.01	5	0
Arteriosclerosis Thickening and loss of elasticity of the walls of ARTERIES of all sizes. There are many forms classified by the types of lesions and arteries involved, such as ATHEROSCLEROSIS with fatty lesions in the ARTERIAL INTIMA of medium and large muscular arteries.	2.02	1	0
Leukemia P388 An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.	3.24	6	0
Lesion of Sciatic Nerve [description not available]	2.02	1	0
Central Nervous System Neoplasm [description not available]	2.42	2	0
Central Nervous System Neoplasms Benign and malignant neoplastic processes that arise from or secondarily involve the brain, spinal cord, or meninges.	2.42	2	0
Allergic Contact Dermatitis [description not available]	2.02	1	0
Dermatitis, Allergic Contact A contact dermatitis due to allergic sensitization to various substances. These substances subsequently produce inflammatory reactions in the skin of those who have acquired hypersensitivity to them as a result of prior exposure.	2.02	1	0
Bilateral Headache [description not available]	4.05	3	1
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.	4.05	3	1
Nervous System Disorders [description not available]	5	3	1
Nervous System Diseases Diseases of the central and peripheral nervous system. This includes disorders of the brain, spinal cord, cranial nerves, peripheral nerves, nerve roots, autonomic nervous system, neuromuscular junction, and muscle.	5	3	1
Blood Pressure, Low [description not available]	2.03	1	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.	2.03	1	0
Delayed Effects, Prenatal Exposure [description not available]	2.03	1	0
Brain Swelling [description not available]	2.94	4	0
Water Intoxication A condition resulting from the excessive retention of water with sodium depletion.	2.03	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)	2.94	4	0
Abnormalities, Drug-Induced Congenital abnormalities caused by medicinal substances or drugs of abuse given to or taken by the mother, or to which she is inadvertently exposed during the manufacture of such substances. The concept excludes abnormalities resulting from exposure to non-medicinal chemicals in the environment.	2.39	2	0
Hyperthyroid [description not available]	2.03	1	0
Hyperthyroidism Hypersecretion of THYROID HORMONES from the THYROID GLAND. Elevated levels of thyroid hormones increase BASAL METABOLIC RATE.	2.03	1	0
Nephritis Inflammation of any part of the KIDNEY.	2.03	1	0
47,XX,+21 [description not available]	2.03	1	0
Down Syndrome A chromosome disorder associated either with an extra chromosome 21 or an effective trisomy for chromosome 21. Clinical manifestations include hypotonia, short stature, brachycephaly, upslanting palpebral fissures, epicanthus, Brushfield spots on the iris, protruding tongue, small ears, short, broad hands, fifth finger clinodactyly, Simian crease, and moderate to severe INTELLECTUAL DISABILITY. Cardiac and gastrointestinal malformations, a marked increase in the incidence of LEUKEMIA, and the early onset of ALZHEIMER DISEASE are also associated with this condition. Pathologic features include the development of NEUROFIBRILLARY TANGLES in neurons and the deposition of AMYLOID BETA-PROTEIN, similar to the pathology of ALZHEIMER DISEASE. (Menkes, Textbook of Child Neurology, 5th ed, p213)	2.03	1	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.	4.48	24	0
Disease, Pulmonary [description not available]	2.95	1	0
Lung Diseases Pathological processes involving any part of the LUNG.	2.95	1	0
Allergic Reaction [description not available]	2.4	2	0
Hypersensitivity Altered reactivity to an antigen, which can result in pathologic reactions upon subsequent exposure to that particular antigen.	2.4	2	0
Rheumatism [description not available]	3.42	1	1
Rheumatic Diseases Disorders of connective tissue, especially the joints and related structures, characterized by inflammation, degeneration, or metabolic derangement.	3.42	1	1
Decerebrate Posturing [description not available]	2.34	2	0
Arboviral Encephalitis [description not available]	2.62	3	0
Hypomelanosis [description not available]	2.04	1	0
Hypopigmentation A condition caused by a deficiency or a loss of melanin pigmentation in the epidermis, also known as hypomelanosis. Hypopigmentation can be localized or generalized, and may result from genetic defects, trauma, inflammation, or infections.	2.04	1	0
Inflammation, Endodontic [description not available]	2.04	1	0
Pulpitis Inflammation of the DENTAL PULP, usually due to bacterial infection in dental caries, tooth fracture, or other conditions causing exposure of the pulp to bacterial invasion. Chemical irritants, thermal factors, hyperemic changes, and other factors may also cause pulpitis.	2.04	1	0
Papilloma, Squamous Cell [description not available]	1.94	1	0
Papilloma A circumscribed benign epithelial tumor projecting from the surrounding surface; more precisely, a benign epithelial neoplasm consisting of villous or arborescent outgrowths of fibrovascular stroma covered by neoplastic cells. (Stedman, 25th ed)	1.94	1	0
Blood Diseases [description not available]	1.95	1	0
Hematologic Diseases Disorders of the blood and blood forming tissues.	1.95	1	0
Parodontosis [description not available]	3.34	1	1
Periodontal Diseases Pathological processes involving the PERIODONTIUM including the gum (GINGIVA), the alveolar bone (ALVEOLAR PROCESS), the DENTAL CEMENTUM, and the PERIODONTAL LIGAMENT.	3.34	1	1
Lassitude [description not available]	1.95	1	0
Fatigue The state of weariness following a period of exertion, mental or physical, characterized by a decreased capacity for work and reduced efficiency to respond to stimuli.	1.95	1	0
Leukemia L5178 An experimental lymphocytic leukemia of mice.	1.96	1	0
Experimental Hepatoma [description not available]	3.36	7	0
Ischemia A hypoperfusion of the BLOOD through an organ or tissue caused by a PATHOLOGIC CONSTRICTION or obstruction of its BLOOD VESSELS, or an absence of BLOOD CIRCULATION.	2.69	3	0
Brittle Bone Disease [description not available]	1.98	1	0
Osteogenesis Imperfecta COLLAGEN DISEASES characterized by brittle, osteoporotic, and easily fractured bones. It may also present with blue sclerae, loose joints, and imperfect dentin formation. Most types are autosomal dominant and are associated with mutations in COLLAGEN TYPE I.	1.98	1	0
Marfan Syndrome, Type I [description not available]	1.98	1	0
Marfan Syndrome An autosomal dominant disorder of CONNECTIVE TISSUE with abnormal features in the heart, the eye, and the skeleton. Cardiovascular manifestations include MITRAL VALVE PROLAPSE, dilation of the AORTA, and aortic dissection. Other features include lens displacement (ectopia lentis), disproportioned long limbs and enlarged DURA MATER (dural ectasia). Marfan syndrome (type 1) is associated with mutations in the gene encoding FIBRILLIN-1 (FBN1), a major element of extracellular microfibrils of connective tissue. Mutations in the gene encoding TYPE II TGF-BETA RECEPTOR (TGFBR2) are associated with Marfan syndrome type 2.	1.98	1	0
Animal Mammary Carcinoma [description not available]	2.39	2	0
Cancer of Pituitary [description not available]	2.9	4	0
Pituitary Neoplasms Neoplasms which arise from or metastasize to the PITUITARY GLAND. The majority of pituitary neoplasms are adenomas, which are divided into non-secreting and secreting forms. Hormone producing forms are further classified by the type of hormone they secrete. Pituitary adenomas may also be characterized by their staining properties (see ADENOMA, BASOPHIL; ADENOMA, ACIDOPHIL; and ADENOMA, CHROMOPHOBE). Pituitary tumors may compress adjacent structures, including the HYPOTHALAMUS, several CRANIAL NERVES, and the OPTIC CHIASM. Chiasmal compression may result in bitemporal HEMIANOPSIA.	2.9	4	0
Urination Disorders Abnormalities in the process of URINE voiding, including bladder control, frequency of URINATION, as well as the volume and composition of URINE.	1.98	1	0
Cherry Red Spot Myoclonus Syndrome [description not available]	2.38	2	0
Corneal Edema An excessive amount of fluid in the cornea due to damage of the epithelium or endothelium causing decreased visual acuity.	1.98	1	0
Sicca Syndrome [description not available]	2.38	2	0
Sjogren's Syndrome Chronic inflammatory and autoimmune disease in which the salivary and lacrimal glands undergo progressive destruction by lymphocytes and plasma cells resulting in decreased production of saliva and tears. The primary form, often called sicca syndrome, involves both KERATOCONJUNCTIVITIS SICCA and XEROSTOMIA. The secondary form includes, in addition, the presence of a connective tissue disease, usually rheumatoid arthritis.	2.38	2	0
Ataxia Impairment of the ability to perform smoothly coordinated voluntary movements. This condition may affect the limbs, trunk, eyes, pharynx, larynx, and other structures. Ataxia may result from impaired sensory or motor function. Sensory ataxia may result from posterior column injury or PERIPHERAL NERVE DISEASES. Motor ataxia may be associated with CEREBELLAR DISEASES; CEREBRAL CORTEX diseases; THALAMIC DISEASES; BASAL GANGLIA DISEASES; injury to the RED NUCLEUS; and other conditions.	2.37	2	0
Diseases, Peripheral Vascular [description not available]	1.98	1	0
Peripheral Vascular Diseases Pathological processes involving any one of the BLOOD VESSELS in the vasculature outside the HEART.	1.98	1	0
Adenoma, beta-Cell [description not available]	1.98	1	0
Insulinoma A benign tumor of the PANCREATIC BETA CELLS. Insulinoma secretes excess INSULIN resulting in HYPOGLYCEMIA.	1.98	1	0
Dysembryoma [description not available]	1.98	1	0
Teratoma A true neoplasm composed of a number of different types of tissue, none of which is native to the area in which it occurs. It is composed of tissues that are derived from three germinal layers, the endoderm, mesoderm, and ectoderm. They are classified histologically as mature (benign) or immature (malignant). (From DeVita Jr et al., Cancer: Principles & Practice of Oncology, 3d ed, p1642)	1.98	1	0
Circulatory Collapse [description not available]	1.98	1	0
Shock A pathological condition manifested by failure to perfuse or oxygenate vital organs.	1.98	1	0
P carinii Infection [description not available]	1.98	1	0
Pneumocystis Infections Infections with species in the genus PNEUMOCYSTIS, a fungus causing interstitial plasma cell pneumonia (PNEUMONIA, PNEUMOCYSTIS) and other infections in humans and other MAMMALS. Immunocompromised patients, especially those with AIDS, are particularly susceptible to these infections. Extrapulmonary sites are rare but seen occasionally.	1.98	1	0
AIDS Seroconversion [description not available]	2.39	2	0
Infections, Chlamydia [description not available]	1.99	1	0
Chlamydia Infections Infections with bacteria of the genus CHLAMYDIA.	1.99	1	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.	2.37	2	0
Hepatoblastoma A malignant neoplasm occurring in young children, primarily in the liver, composed of tissue resembling embryonal or fetal hepatic epithelium, or mixed epithelial and mesenchymal tissues. (Stedman, 25th ed)	2.39	2	0
Mast-Cell Leukemia [description not available]	1.99	1	0
Leukemia, Mast-Cell A form of systemic mastocytosis (MASTOCYTOSIS, SYSTEMIC) characterized by the presence of large numbers of tissue MAST CELLS in the peripheral blood without skin lesions. It is a high-grade LEUKEMIA disease with bone marrow smear of	1.99	1	0
Congenital Hypocupremia [description not available]	1.99	1	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)	1.99	1	0
Mast-Cell Sarcoma A unifocal malignant tumor that consists of atypical pathological MAST CELLS without systemic involvement. It causes local destructive growth in organs other than in skin or bone marrow.	2.39	2	0
Experimental Mammary Neoplasms [description not available]	1.99	1	0
Dementias, Transmissible [description not available]	1.99	1	0
Infections, Listeria [description not available]	2.39	2	0
Cerebral Pseudosclerosis [description not available]	1.99	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.	1.99	1	0
AIDS, Murine [description not available]	1.99	1	0
Corynebacterium diphtheriae Infection [description not available]	1.99	1	0
Diphtheria A localized infection of mucous membranes or skin caused by toxigenic strains of CORYNEBACTERIUM DIPHTHERIAE. It is characterized by the presence of a pseudomembrane at the site of infection. DIPHTHERIA TOXIN, produced by C. diphtheriae, can cause myocarditis, polyneuritis, and other systemic toxic effects.	1.99	1	0
Cell Transformation, Viral An inheritable change in cells manifested by changes in cell division and growth and alterations in cell surface properties. It is induced by infection with a transforming virus.	2.67	3	0
Macular Holes [description not available]	3.79	2	1
Intraocular Pressure The pressure of the fluids in the eye.	6.51	11	1
Retinal Perforations Perforations through the whole thickness of the retina including the macula as the result of inflammation, trauma, degeneration, etc. The concept includes retinal breaks, tears, dialyses, and holes.	3.79	2	1
Glaucoma, Suspect [description not available]	3.38	1	1
Ocular Hypertension A condition in which the intraocular pressure is elevated above normal and which may lead to glaucoma.	3.38	1	1
Arterial Obstructive Diseases [description not available]	2	1	0
Anterior Circulation Transient Ischemic Attack [description not available]	2	1	0
Arterial Diseases, Cerebral [description not available]	2	1	0
Arterial Occlusive Diseases Pathological processes which result in the partial or complete obstruction of ARTERIES. They are characterized by greatly reduced or absence of blood flow through these vessels. They are also known as arterial insufficiency.	2	1	0
Cerebral Arterial Diseases Pathological conditions of intracranial ARTERIES supplying the CEREBRUM. These diseases often are due to abnormalities or pathological processes in the ANTERIOR CEREBRAL ARTERY; MIDDLE CEREBRAL ARTERY; and POSTERIOR CEREBRAL ARTERY.	2	1	0
Ischemic Attack, Transient Brief reversible episodes of focal, nonconvulsive ischemic dysfunction of the brain having a duration of less than 24 hours, and usually less than one hour, caused by transient thrombotic or embolic blood vessel occlusion or stenosis. Events may be classified by arterial distribution, temporal pattern, or etiology (e.g., embolic vs. thrombotic). (From Adams et al., Principles of Neurology, 6th ed, pp814-6)	2	1	0
Autoimmune Diabetes [description not available]	2	1	0
Diabetes Mellitus, Type 1 A subtype of DIABETES MELLITUS that is characterized by INSULIN deficiency. It is manifested by the sudden onset of severe HYPERGLYCEMIA, rapid progression to DIABETIC KETOACIDOSIS, and DEATH unless treated with insulin. The disease may occur at any age, but is most common in childhood or adolescence.	2	1	0
Alcohol Withdrawal Seizures A condition where seizures occur in association with ethanol abuse (ALCOHOLISM) without other identifiable causes. Seizures usually occur within the first 6-48 hours after the cessation of alcohol intake, but may occur during periods of alcohol intoxication. Single generalized tonic-clonic motor seizures are the most common subtype, however, STATUS EPILEPTICUS may occur. (Adams et al., Principles of Neurology, 6th ed, p1174)	2	1	0
Complex IV Deficiency [description not available]	2	1	0
Pheochromocytoma, Extra-Adrenal [description not available]	2.01	1	0
Pheochromocytoma A usually benign, well-encapsulated, lobular, vascular tumor of chromaffin tissue of the ADRENAL MEDULLA or sympathetic paraganglia. The cardinal symptom, reflecting the increased secretion of EPINEPHRINE and NOREPINEPHRINE, is HYPERTENSION, which may be persistent or intermittent. During severe attacks, there may be HEADACHE; SWEATING, palpitation, apprehension, TREMOR; PALLOR or FLUSHING of the face, NAUSEA and VOMITING, pain in the CHEST and ABDOMEN, and paresthesias of the extremities. The incidence of malignancy is as low as 5% but the pathologic distinction between benign and malignant pheochromocytomas is not clear. (Dorland, 27th ed; DeVita Jr et al., Cancer: Principles & Practice of Oncology, 3d ed, p1298)	2.01	1	0
Leukemia, Lymphocytic, T Cell [description not available]	2.01	1	0
Leukemia, T-Cell A malignant disease of the T-LYMPHOCYTES in the bone marrow, thymus, and/or blood.	2.01	1	0
Pleurisy INFLAMMATION of PLEURA, the lining of the LUNG. When PARIETAL PLEURA is involved, there is pleuritic CHEST PAIN.	2.01	1	0
Angor Pectoris [description not available]	4.59	3	2
Angina Pectoris The symptom of paroxysmal pain consequent to MYOCARDIAL ISCHEMIA usually of distinctive character, location and radiation. It is thought to be provoked by a transient stressful situation during which the oxygen requirements of the MYOCARDIUM exceed that supplied by the CORONARY CIRCULATION.	4.59	3	2
Manganese Poisoning Manganese poisoning is associated with chronic inhalation of manganese particles by individuals who work with manganese ore. Clinical features include CONFUSION; HALLUCINATIONS; and an extrapyramidal syndrome (PARKINSON DISEASE, SECONDARY) that includes rigidity; DYSTONIA; retropulsion; and TREMOR. (Adams, Principles of Neurology, 6th ed, p1213)	2.64	3	0
Acne [description not available]	2.87	1	0
Congenital Adrenal Hyperplasia [description not available]	2.87	1	0
Hirsutism A condition observed in WOMEN and CHILDREN when there is excess coarse body hair of an adult male distribution pattern, such as facial and chest areas. It is the result of elevated ANDROGENS from the OVARIES, the ADRENAL GLANDS, or exogenous sources. The concept does not include HYPERTRICHOSIS, which is an androgen-independent excessive hair growth.	4.66	2	1
Dermatitis Seborrheica [description not available]	2.87	1	0
Acne Vulgaris A chronic disorder of the pilosebaceous apparatus associated with an increase in sebum secretion. It is characterized by open comedones (blackheads), closed comedones (whiteheads), and pustular nodules. The cause is unknown, but heredity and age are predisposing factors.	2.87	1	0
Adrenal Hyperplasia, Congenital A group of inherited disorders of the ADRENAL GLANDS, caused by enzyme defects in the synthesis of cortisol (HYDROCORTISONE) and/or ALDOSTERONE leading to accumulation of precursors for ANDROGENS. Depending on the hormone imbalance, congenital adrenal hyperplasia can be classified as salt-wasting, hypertensive, virilizing, or feminizing. Defects in STEROID 21-HYDROXYLASE; STEROID 11-BETA-HYDROXYLASE; STEROID 17-ALPHA-HYDROXYLASE; 3-beta-hydroxysteroid dehydrogenase (3-HYDROXYSTEROID DEHYDROGENASES); TESTOSTERONE 5-ALPHA-REDUCTASE; or steroidogenic acute regulatory protein; among others, underlie these disorders.	2.87	1	0
Dermatitis, Seborrheic A chronic inflammatory disease of the skin with unknown etiology. It is characterized by moderate ERYTHEMA, dry, moist, or greasy (SEBACEOUS GLAND) scaling and yellow crusted patches on various areas, especially the scalp, that exfoliate as dandruff. Seborrheic dermatitis is common in children and adolescents with HIV INFECTIONS.	2.87	1	0
Aspergillus Infection [description not available]	1.95	1	0
Keratitis, Ulcerative [description not available]	1.95	1	0
Injuries, Eye [description not available]	1.95	1	0
Agricultural Worker Disease [description not available]	1.95	1	0
Aspergillosis Infections with fungi of the genus ASPERGILLUS.	1.95	1	0
Corneal Ulcer Loss of epithelial tissue from the surface of the cornea due to progressive erosion and necrosis of the tissue; usually caused by bacterial, fungal, or viral infection.	1.95	1	0
Eye Injuries Damage or trauma inflicted to the eye by external means. The concept includes both surface injuries and intraocular injuries.	1.95	1	0
Keratitis Inflammation of the cornea.	1.95	1	0
Plasma Cell Tumor [description not available]	2.35	2	0
Plasmacytoma Any discrete, presumably solitary, mass of neoplastic PLASMA CELLS either in BONE MARROW or various extramedullary sites.	2.35	2	0
Dermatitis, Eczematous [description not available]	3.34	1	1
Eczema A pruritic papulovesicular dermatitis occurring as a reaction to many endogenous and exogenous agents (Dorland, 27th ed).	3.34	1	1
Eye Disorders [description not available]	4.11	6	0
Diseases, Occupational [description not available]	1.95	1	0
Diseases of Pharynx [description not available]	1.95	1	0
Eye Diseases Diseases affecting the eye.	4.11	6	0
Pink Eye [description not available]	1.95	1	0
Conjunctivitis INFLAMMATION of the CONJUNCTIVA.	1.95	1	0
Erythema Redness of the skin produced by congestion of the capillaries. This condition may result from a variety of disease processes.	2.64	3	0
Infections, Mycobacterium [description not available]	1.95	1	0
Mycobacterium Infections Infections with bacteria of the genus MYCOBACTERIUM.	1.95	1	0
Diabetes Mellitus A heterogeneous group of disorders characterized by HYPERGLYCEMIA and GLUCOSE INTOLERANCE.	5.68	11	2
Infant, Newborn, Diseases Diseases of newborn infants present at birth (congenital) or developing within the first month of birth. It does not include hereditary diseases not manifesting at birth or within the first 30 days of life nor does it include inborn errors of metabolism. Both HEREDITARY DISEASES and METABOLISM, INBORN ERRORS are available as general concepts.	1.95	1	0
Candidiasis, Cutaneous Candidiasis of the skin manifested as eczema-like lesions of the interdigital spaces, perleche, or chronic paronychia. (Dorland, 27th ed)	1.95	1	0
Bronchitis Inflammation of the large airways in the lung including any part of the BRONCHI, from the PRIMARY BRONCHI to the TERTIARY BRONCHI.	3.74	2	1
Respiratory Tract Neoplasms New abnormal growth of tissue in the RESPIRATORY SYSTEM.	1.95	1	0
Pericementitis [description not available]	1.95	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)	1.95	1	0
Enteric Fever [description not available]	1.95	1	0
Abscess Accumulation of purulent material in tissues, organs, or circumscribed spaces, usually associated with signs of infection.	1.95	1	0
Typhoid Fever An acute systemic febrile infection caused by SALMONELLA TYPHI, a serotype of SALMONELLA ENTERICA.	1.95	1	0
Abortion, Veterinary Premature expulsion of the FETUS in animals.	1.95	1	0
Sarcoma 180 An experimental sarcoma of mice.	2.36	2	0
Infection, Toxoplasma gondii [description not available]	1.98	1	0
Toxoplasmosis The acquired form of infection by Toxoplasma gondii in animals and man.	1.98	1	0
Rida [description not available]	1.98	1	0
Airway Obstruction Any hindrance to the passage of air into and out of the lungs.	1.98	1	0
Bronchial Hyperreactivity Tendency of the smooth muscle of the tracheobronchial tree to contract more intensely in response to a given stimulus than it does in the response seen in normal individuals. This condition is present in virtually all symptomatic patients with asthma. The most prominent manifestation of this smooth muscle contraction is a decrease in airway caliber that can be readily measured in the pulmonary function laboratory.	1.98	1	0
Bile Duct Obstruction, Intrahepatic [description not available]	1.98	1	0
Cholestasis, Intrahepatic Impairment of bile flow due to injury to the HEPATOCYTES; BILE CANALICULI; or the intrahepatic bile ducts (BILE DUCTS, INTRAHEPATIC).	1.98	1	0
Airway Hyper-Responsiveness [description not available]	1.97	1	0
Choriocarcinoma A malignant metastatic form of trophoblastic tumors. Unlike the HYDATIDIFORM MOLE, choriocarcinoma contains no CHORIONIC VILLI but rather sheets of undifferentiated cytotrophoblasts and syncytiotrophoblasts (TROPHOBLASTS). It is characterized by the large amounts of CHORIONIC GONADOTROPIN produced. Tissue origins can be determined by DNA analyses: placental (fetal) origin or non-placental origin (CHORIOCARCINOMA, NON-GESTATIONAL).	1.97	1	0
Eye Manifestations Ocular disorders attendant upon non-ocular disease or injury.	3.33	1	1
Extravascular Hemolysis [description not available]	2.35	2	0
Hemolysis The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.	2.35	2	0
Anaphylactic Reaction [description not available]	2.64	3	0
Anaphylaxis An acute hypersensitivity reaction due to exposure to a previously encountered ANTIGEN. The reaction may include rapidly progressing URTICARIA, respiratory distress, vascular collapse, systemic SHOCK, and death.	2.64	3	0
Salmonella Infections, Animal Infections in animals with bacteria of the genus SALMONELLA.	1.95	1	0
Atypical Endometrial Hyperplasia A benign form of endometrial hyperplasia with increased number of cells with atypia. The atypical cells are large and irregular and have an increased nuclear/cytoplasmic ratio. The risk of progression to endometrial carcinoma rises with the increasing degree of cell atypia.	3.33	1	1
Hemorrhage, Uterine [description not available]	3.33	1	1
Endometrial Hyperplasia Benign proliferation of the ENDOMETRIUM in the UTERUS. Endometrial hyperplasia is classified by its cytology and glandular tissue. There are simple, complex (adenomatous without atypia), and atypical hyperplasia representing also the ascending risk of becoming malignant.	3.33	1	1
Menopause The last menstrual period. Permanent cessation of menses (MENSTRUATION) is usually defined after 6 to 12 months of AMENORRHEA in a woman over 45 years of age. In the United States, menopause generally occurs in women between 48 and 55 years of age.	3.33	1	1
Uterine Hemorrhage Bleeding from blood vessels in the UTERUS, sometimes manifested as vaginal bleeding.	3.33	1	1
Glaucoma An ocular disease, occurring in many forms, having as its primary characteristics an unstable or a sustained increase in the intraocular pressure which the eye cannot withstand without damage to its structure or impairment of its function. The consequences of the increased pressure may be manifested in a variety of symptoms, depending upon type and severity, such as excavation of the optic disk, hardness of the eyeball, corneal anesthesia, reduced visual acuity, seeing of colored halos around lights, disturbed dark adaptation, visual field defects, and headaches. (Dictionary of Visual Science, 4th ed)	6.32	9	1
Deficiency, Vitamin A [description not available]	1.95	1	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)	1.95	1	0
Anorexia Nervosa An eating disorder that is characterized by the lack or loss of APPETITE, known as ANOREXIA. Other features include excess fear of becoming OVERWEIGHT; BODY IMAGE disturbance; significant WEIGHT LOSS; refusal to maintain minimal normal weight; and AMENORRHEA. This disorder occurs most frequently in adolescent females. (APA, Thesaurus of Psychological Index Terms, 1994)	1.94	1	0
Carcinoma, Thymic [description not available]	1.94	1	0
Cancer of the Thymus [description not available]	1.94	1	0
Thymoma A neoplasm originating from thymic tissue, usually benign, and frequently encapsulated. Although it is occasionally invasive, metastases are extremely rare. It consists of any type of thymic epithelial cell as well as lymphocytes that are usually abundant. Malignant lymphomas that involve the thymus, e.g., lymphosarcoma, Hodgkin's disease (previously termed granulomatous thymoma), should not be regarded as thymoma. (From Stedman, 25th ed)	1.94	1	0
Thymus Neoplasms Tumors or cancer of the THYMUS GLAND.	1.94	1	0
Anemia, Hypochromic Anemia characterized by a decrease in the ratio of the weight of hemoglobin to the volume of the erythrocyte, i.e., the mean corpuscular hemoglobin concentration is less than normal. The individual cells contain less hemoglobin than they could have under optimal conditions. Hypochromic anemia may be caused by iron deficiency from a low iron intake, diminished iron absorption, or excessive iron loss. It can also be caused by infections or other diseases, therapeutic drugs, lead poisoning, and other conditions. (Stedman, 25th ed; from Miale, Laboratory Medicine: Hematology, 6th ed, p393)	1.95	1	0
Abnormalities, Sex Chromosome [description not available]	1.95	1	0
Diabetic Angiopathies VASCULAR DISEASES that are associated with DIABETES MELLITUS.	4.58	6	1
Nephrotic Syndrome A condition characterized by severe PROTEINURIA, greater than 3.5 g/day in an average adult. The substantial loss of protein in the urine results in complications such as HYPOPROTEINEMIA; generalized EDEMA; HYPERTENSION; and HYPERLIPIDEMIAS. Diseases associated with nephrotic syndrome generally cause chronic kidney dysfunction.	1.94	1	0
Diseases in Twins Disorders affecting TWINS, one or both, at any age.	1.95	1	0
Infant, Premature, Diseases Diseases that occur in PREMATURE INFANTS.	1.95	1	0
Antibiotic-Associated Colitis [description not available]	1.95	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.	1.95	1	0
Birth Weight The mass or quantity of heaviness of an individual at BIRTH. It is expressed by units of pounds or kilograms.	1.95	1	0
Myelopathy [description not available]	2.35	2	0
Spinal Cord Diseases Pathologic conditions which feature SPINAL CORD damage or dysfunction, including disorders involving the meninges and perimeningeal spaces surrounding the spinal cord. Traumatic injuries, vascular diseases, infections, and inflammatory/autoimmune processes may affect the spinal cord.	2.35	2	0
Farsightedness [description not available]	2.35	2	0
Nearsightedness [description not available]	2.35	2	0
Hyperopia A refractive error in which rays of light entering the eye parallel to the optic axis are brought to a focus behind the retina, as a result of the eyeball being too short from front to back. It is also called farsightedness because the near point is more distant than it is in emmetropia with an equal amplitude of accommodation. (Dorland, 27th ed)	2.35	2	0
Myopia A refractive error in which rays of light entering the EYE parallel to the optic axis are brought to a focus in front of the RETINA when accommodation (ACCOMMODATION, OCULAR) is relaxed. This results from an overly curved CORNEA or from the eyeball being too long from front to back. It is also called nearsightedness.	2.35	2	0
Gastroduodenal Ulcer [description not available]	1.95	1	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).	1.95	1	0
Ametropia [description not available]	1.95	1	0
Refractive Errors Deviations from the average or standard indices of refraction of the eye through its dioptric or refractive apparatus.	1.95	1	0
BH4 Deficiency [description not available]	1.95	1	0
Phenylketonurias A group of autosomal recessive disorders marked by a deficiency of the hepatic enzyme PHENYLALANINE HYDROXYLASE or less frequently by reduced activity of DIHYDROPTERIDINE REDUCTASE (i.e., atypical phenylketonuria). Classical phenylketonuria is caused by a severe deficiency of phenylalanine hydroxylase and presents in infancy with developmental delay; SEIZURES; skin HYPOPIGMENTATION; ECZEMA; and demyelination in the central nervous system. (From Adams et al., Principles of Neurology, 6th ed, p952).	1.95	1	0
Hallucination of Body Sensation [description not available]	2.35	2	0
Hallucinations Subjectively experienced sensations in the absence of an appropriate stimulus, but which are regarded by the individual as real. They may be of organic origin or associated with MENTAL DISORDERS.	2.35	2	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
Human Trichinellosis [description not available]	1.95	1	0
Trichinellosis An infection with TRICHINELLA. It is caused by eating raw or undercooked meat that is infected with larvae of nematode worms TRICHINELLA genus. All members of the TRICHINELLA genus can infect human in addition to TRICHINELLA SPIRALIS, the traditional etiological agent. It is distributed throughout much of the world and is re-emerging in some parts as a public health hazard and a food safety problem.	1.95	1	0
Appetite Disorders [description not available]	3.33	1	1
Leiomyosarcoma, Epithelioid [description not available]	3.33	1	1
Cancer of Rectum [description not available]	3.33	1	1
Feeding and Eating Disorders A group of disorders characterized by physiological and psychological disturbances in appetite or food intake.	3.33	1	1
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)	3.33	1	1
Rectal Neoplasms Tumors or cancer of the RECTUM.	3.33	1	1
Arthropathies [description not available]	1.94	1	0
Angle's Classification [description not available]	1.94	1	0
Mandibular Fractures Fractures of the lower jaw.	1.94	1	0
Periostitis Inflammation of the periosteum. The condition is generally chronic, and is marked by tenderness and swelling of the bone and an aching pain. Acute periostitis is due to infection, is characterized by diffuse suppuration, severe pain, and constitutional symptoms, and usually results in necrosis. (Dorland, 27th ed)	1.94	1	0
Costen's Syndrome [description not available]	1.94	1	0
Mandibular Diseases Diseases involving the MANDIBLE.	1.94	1	0
Joint Diseases Diseases involving the JOINTS.	1.94	1	0
Malocclusion Such malposition and contact of the maxillary and mandibular teeth as to interfere with the highest efficiency during the excursive movements of the jaw that are essential for mastication. (Jablonski, Illustrated Dictionary of Dentistry, 1982)	1.94	1	0
Starvation Lengthy and continuous deprivation of food. (Stedman, 25th ed)	1.94	1	0
Nutritional Disorders [description not available]	1.94	1	0
Age-Related Osteoporosis [description not available]	1.94	1	0
Androgenization [description not available]	1.94	1	0
Anemia A reduction in the number of circulating ERYTHROCYTES or in the quantity of HEMOGLOBIN.	1.94	1	0
Cachexia General ill health, malnutrition, and weight loss, usually associated with chronic disease.	1.94	1	0
Nutrition Disorders Disorders caused by nutritional imbalance, either overnutrition or undernutrition.	1.94	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.	1.94	1	0
Postpartum Amenorrhea [description not available]	1.94	1	0
Amenorrhea Absence of menstruation.	1.94	1	0
Amblyopia, Developmental [description not available]	1.94	1	0
Conjugate Nystagmus [description not available]	2.35	2	0
Amblyopia A nonspecific term referring to impaired vision. Major subcategories include stimulus deprivation-induced amblyopia and toxic amblyopia. Stimulus deprivation-induced amblyopia is a developmental disorder of the visual cortex. A discrepancy between visual information received by the visual cortex from each eye results in abnormal cortical development. STRABISMUS and REFRACTIVE ERRORS may cause this condition. Toxic amblyopia is a disorder of the OPTIC NERVE which is associated with ALCOHOLISM, tobacco SMOKING, and other toxins and as an adverse effect of the use of some medications.	1.94	1	0
Cystinuria An inherited disorder due to defective reabsorption of CYSTINE and other BASIC AMINO ACIDS by the PROXIMAL RENAL TUBULES. This form of aminoaciduria is characterized by the abnormally high urinary levels of cystine; LYSINE; ARGININE; and ORNITHINE. Mutations involve the amino acid transport protein gene SLC3A1.	2.35	2	0
Amaurosis [description not available]	1.94	1	0
Hyphema Bleeding in the anterior chamber of the eye.	1.94	1	0
Purpura, Thrombopenic [description not available]	1.94	1	0
Blindness The inability to see or the loss or absence of perception of visual stimuli. This condition may be the result of EYE DISEASES; OPTIC NERVE DISEASES; OPTIC CHIASM diseases; or BRAIN DISEASES affecting the VISUAL PATHWAYS or OCCIPITAL LOBE.	1.94	1	0
Purpura, Thrombocytopenic Any form of purpura in which the PLATELET COUNT is decreased. Many forms are thought to be caused by immunological mechanisms.	1.94	1	0
Bleb [description not available]	1.94	1	0
Mouth Diseases Diseases involving the MOUTH.	1.94	1	0
Aprosodia [description not available]	1.94	1	0
Cirrhoses, Experimental Liver [description not available]	2.35	2	0
Testicular Diseases Pathological processes of the TESTIS.	1.94	1	0
Hemosiderosis Conditions in which there is a generalized increase in the iron stores of body tissues, particularly of liver and the MONONUCLEAR PHAGOCYTE SYSTEM, without demonstrable tissue damage. The name refers to the presence of stainable iron in the tissue in the form of hemosiderin.	1.94	1	0
Urinary Calculi Low-density crystals or stones in any part of the URINARY TRACT. Their chemical compositions often include CALCIUM OXALATE, magnesium ammonium phosphate (struvite), CYSTINE, or URIC ACID.	1.94	1	0
Aminoaciduria, Renal [description not available]	1.94	1	0

cyclopentane

Description

Cross-References

Synonyms (53)

Research Excerpts

Effects

Toxicity

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Dosage Studied

Roles (1)

Drug Classes (3)

Protein Targets (5)

Potency Measurements

Bioassays (1)

Research

Studies (10,288)

Market Indicators

Research Demand Index: 73.89

Study Types