malonic acid profile

malonic acid : An alpha,omega-dicarboxylic acid in which the two carboxy groups are separated by a single methylene group. [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]

dicarboxylic acid : Any carboxylic acid containing two carboxy groups. [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	867
CHEMBL ID	7942
CHEBI ID	30794
SCHEMBL ID	1471092
SCHEMBL ID	336
MeSH ID	M0095922

Synonym
dicarboxymethane
methanedicarboxylic acid
wln: qv1vq
nsc8124 ,
carboxyacetic acid
usaf ek-695
nsc-8124
h2malo
CHEBI:30794 ,
hooc-ch2-cooh
LMFA01170041
MLI ,
propanedioic acid malonic acid
inchi=1/c3h4o4/c4-2(5)1-3(6)7/h1h2,(h,4,5)(h,6,7
malonic acid (8ci)
1,3-propanedioic acid
ai3-15375
propanedioic acid (9ci)
kyselina malonova [czech]
einecs 205-503-0
brn 1751370
nsc 8124
propanedioic acid
141-82-2
C04025
C00383
alpha,omega-dicarboxylic acid
C02028
dicarboxylic acid
MALONATE ,
dicarboxylate ,
malonic acid
propanediolic acid
metahnedicarboxylic acid
malonic acid, reagentplus(r), 99%
1O4M
bdbm14673
2FAH
DB02175
592A9849-68C3-4635-AA3D-CBC44965EA3A
CHEMBL7942
FT-0690260
FT-0693474
M0028
AKOS000119034
NCGC00248681-01
dtxcid401659
tox21_200534
cas-141-82-2
dtxsid7021659 ,
NCGC00258088-01
SCHEMBL1471092
c3h4o4
propane-1,3-dioic acid
kyselina malonova
hsdb 8437
unii-9kx7zmg0mk
9kx7zmg0mk ,
4-02-00-01874 (beilstein handbook reference)
BP-11453
FT-0628128
FT-0628127
malonic acid [mi]
malonic acid [inci]
S3029
SCHEMBL336
F1908-0177
malonicacid
ch2(cooh)2
methanedicarbonic acid
STR00614
mfcd00002707
J-521669
malonic acid, anhydrous, free-flowing, redi-dri(tm), reagentplus(r), 99%
malonic acid, certified reference material, tracecert(r)
malonic acid, sublimed grade, >=99.95% trace metals basis
malonic acid, saj first grade, >=99.0%
malonic acid, analytical standard
AC8295
malonic acid, 99%
malonic acid, vetec(tm) reagent grade, 98%
Z57965450
malonate dicarboxylic acid
propanedioic acid dithallium salt
LML ,
dicarboxylic acid c3; propanediolic acid; methanedicarboxylic acid
CS-W019962
BCP05571
Q421972
1,3-propanoic acid
SY001875
AMY11201
STL194278
malonic acid, 99.5%
EN300-18457

Excerpt	Reference	Relevance
"Malonic aciduria is an extremely rare inborn error of metabolism due to malonyl-CoA decarboxylase deficiency. "	( Heterogenous Clinical Landscape in a Consanguineous Malonic Aciduria Family. Abily-Donval, L; Bekri, S; Goldenberg, A; Marret, S; Salomons, GS; Snanoudj, S; Sudrié-Arnaud, B; Tebani, A; Torre, S, 2021)	2.31
"Malonic acid is a reversible inhibitor of mitochondrial enzyme complex-II, induces energy crisis and free radical generation."	( Protective effect of 3-n-butylphthalide against intrastriatal injection of malonic acid-induced neurotoxicity and biochemical alteration in rats. Yuan, C; Zhao, Y; Zheng, L, 2022)	1.67
"Malonic acid (MA) is a reversible inhibitor of succinate dehydrogenase (SDH) which induces mitochondrial dysfunction followed by secondary excitotoxicity and apoptosis due to generation of reactive oxygen species. "	( Synergistical neuroprotection of rofecoxib and statins against malonic acid induced Huntington's disease like symptoms and related cognitive dysfunction in rats. Kalonia, H; Kumar, A; Mishra, J; Sharma, N, 2013)	2.07
"Malonic acidaemia is an inborn error of metabolism that accumulates malonate, a competitive succinate dehydrogenase (SDH; EC 1.3.99.1) inhibitor. "	( Intrastriatal malonate administration induces convulsive behaviour in rats. Fleck, J; Mello, CF; Ribeiro, MC; Rubin, MA; Schneider, CM; Sinhorin, VD, 2004)	1.77
"Malonic aciduria is a rare autosomal recessive disorder caused by deficiency of malonyl-CoA decarboxylase, encoded by the MLYCD gene. "	( Fatal malonyl CoA decarboxylase deficiency due to maternal uniparental isodisomy of the telomeric end of chromosome 16. Ciani, F; Donati, MA; Genuardi, M; la Marca, G; Malvagia, S; Morrone, A; Papi, L; Pasquini, E; Scholte, HR; Zammarchi, E, 2007)	1.78

Excerpt	Reference	Relevance
"Malonic acid derivatives have been successfully applied in a Ag-catalyzed decarboxylative fluorination reaction, providing an unprecedented route to either gem-difluoroalkanes or α-fluorocarboxylic acids by the judicious selection of base and solvent. "	( Ag-Catalyzed Chemoselective Decarboxylative Mono- and gem-Difluorination of Malonic Acid Derivatives. Chen, JP; Guo, CY; Wang, Z; Yang, C, 2019)	2.19
"Malonic acid has been observed in the free troposphere and as a component of tropospheric aerosol, among other dicarboxylic acids. "	( Phase diagrams and water activities of aqueous ammonium salts of malonic acid. Beyer, KD; Reusch, B; Richardson, M, 2011)	2.05
"N-Malonic acid conjugates have been previously isolated from peanut either as a natural constituent or after feeding with xenobiotics."	( N-malonyltransferases from peanut. Feser, C; Heller, W; Matern, U, 1984)	0.83

Excerpt	Reference	Relevance
" Weak acids that are normal cellular metabolites are not toxic in vivo, but weak acids carrying cytotoxic groups offer the potential for selective uptake and toxicity under the conditions of low pHe that exist in many solid tumours."	( Selective cellular acidification and toxicity of weak organic acids in an acidic microenvironment. Dobrowsky, E; Karuri, AR; Tannock, IF, 1993)	0.29
" Overall, these results highlight the importance of energy balance to the function of DA and 5-HT neurons and to the toxic effects of MDMA."	( Enhancement of 3,4-methylenedioxymethamphetamine neurotoxicity by the energy inhibitor malonate. Burrows, KB; Gudelsky, GA; Nixdorf, WL; Yamamoto, BK, 2001)	0.31
" The pathomechanisms involved are still unknown, a contribution of toxic organic acids, in particular MMA, has been suggested."	( Neurodegeneration in methylmalonic aciduria involves inhibition of complex II and the tricarboxylic acid cycle, and synergistically acting excitotoxicity. Farkas, LM; Feyh, P; Hinz, A; Hoffmann, GF; Hörster, F; Kölker, S; Mayatepek, E; Okun, JG; Sauer, S; Unsicker, K, 2002)	0.61
" Other experiments showed that these fullerene derivatives become toxic when irradiated with UVA or UVB light."	( Cytotoxicity and photocytotoxicity of a dendritic C(60) mono-adduct and a malonic acid C(60) tris-adduct on Jurkat cells. Boehm, F; Brellreich, M; Cantrell, A; Hirsch, A; Moussa, F; Rancan, F; Rosan, S; Schoenberger, H, 2002)	0.55
"Minocycline has been shown to exert neuroprotection against a wide variety of toxic insults both in vitro and in vivo."	( In vivo studies on the protective role of minocycline against excitotoxicity caused by malonate or N-methyl-d-aspartate. Aguirre, N; Goñi-Allo, B; Jordán, J; Ramos, M, 2005)	0.33
" Finally, the dopamine transporter inhibitor GBR 12909 completely prevented dopamine neurotoxicity caused by the malonate/MDMA combination and reversed the exacerbating toxic effects of malonate on MDMA-induced 5-HT depletion without significantly altering the hyperthermic response."	( Studies on striatal neurotoxicity caused by the 3,4-methylenedioxymethamphetamine/ malonate combination: implications for serotonin/dopamine interactions. Aguirre, N; Goñi-Allo, B; Herv'as, I; Lasheras, B; Ramos, M, 2006)	0.33
" Our findings suggest that this toxic model is not reflective or predictive of findings in genetic mouse models, and may not be useful as a preclinical screen for HD therapeutics."	( Cystamine and ethyl-eicosapentaenoic acid treatment fail to prevent malonate-induced striatal toxicity in mice. Leavitt, BR; Sivananthan, SN, 2011)	0.37
"Asbestos fibers are highly toxic (Group 1 carcinogen) due to their high aspect ratio, durability, and the presence of iron."	( Siderophore-mediated iron removal from chrysotile: Implications for asbestos toxicity reduction and bioremediation. Casper, B; Christofidou-Solomidou, M; Gonneau, C; Mohanty, SK; Pietrofesa, RA; Salamatipour, A; Willenbring, JK, 2018)	0.48

Excerpt	Reference	Relevance
" In addition, it was checked that this neuroprotective effect of riluzole against systemic 3-nitropropionic acid did not result from a decreased bioavailability of the neurotoxin or a direct action of riluzole on 3-nitropropionic acid-induced inhibition of succinate dehydrogenase."	( Riluzole protects from motor deficits and striatal degeneration produced by systemic 3-nitropropionic acid intoxication in rats. Brouillet, E; Guyot, MC; Hantraye, P; Mazière, M; Palfi, S; Stutzmann, JM, 1997)	0.3
" We also investigated possible uses of DES in solubilizing poorly soluble compounds for enhanced bioavailability in early drug development such as toxicology studies."	( Characterization of thermal behavior of deep eutectic solvents and their potential as drug solubilization vehicles. Morrison, HG; Neervannan, S; Sun, CC, 2009)	0.35
" The bioavailability of strontium metal cations in the body and their kinetics of release from materials will depend on their local environment."	( 87Sr solid-state NMR as a structurally sensitive tool for the investigation of materials: antiosteoporotic pharmaceuticals and bioactive glasses. Bonhomme, C; Diogo, CC; Du, J; Folliet, N; Gervais, C; Hanna, JV; Iuga, D; Jallot, E; Lacroix, J; Lao, J; Laurencin, D; Nedelec, JM; Pourpoint, F; Smith, ME; Xiang, Y, 2012)	0.38
" Tetracyclines form metal-complexes in natural waters, which could reduce their bioavailability for bacterial uptake."	( Organic acids enhance bioavailability of tetracycline in water to Escherichia coli for uptake and expression of antibiotic resistance. Boyd, SA; Li, H; Teppen, BJ; Tiedje, JM; Zhang, Y, 2014)	0.4
" Significant enhancement of bioavailability was observed in eutectics (3."	( Multicomponent solid forms of felodipine: preparation, characterisation, physicochemical and in-vivo studies. Chadha, R; Haneef, J; Sharma, M, 2017)	0.46

Excerpt	Relevance	Reference
" Experiments investigating the dose-response relationship, glucocorticoid sensitivity of the preparation, and the role of the mitochondria in the aldosterone response in this preparation are presented."	( Further observations of aldosterone response in barnacle muscle fibers. Tallitsch, RB, 1983)	0.27
"Sensitive and simple spectrophotometric (Method I) and spectrofluorimetric (Method II) methods were developed and validated for the determination of oxybutynin HCl (OXB) in its dosage forms."	( Determination of oxybutynin in pharmaceuticals via reaction with mixed acids anhydrides: application to content uniformity testing. Belal, F; El-Enany, N; Elmansi, H; Walash, MI, 2011)	0.37
" Initially, a curve time- and dose-response to MMA (1-10 mM), MA (1-10 mM) and IP (63-500 μM) was performed."	( Ilex paraguariensis Attenuates Changes in Mortality, Behavioral and Biochemical Parameters Associated to Methyl Malonate or Malonate Exposure in Drosophila melanogaster. Bianchini, MC; Boligon, AA; Carriço, MRS; de Gomes, MG; Hassan, W; Portela, JL; Puntel, RL; Roehrs, R; Soares, FAA, 2019)	0.51

Role	Description
human metabolite	Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Class	Description
alpha,omega-dicarboxylic acid
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathway	Proteins	Compounds
Leucine, isoleucine and valine metabolism	24	70
fatty acid u03C9-oxidation	0	8
Biochemical pathways: part I	0	466

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
RAR-related orphan receptor gamma	Mus musculus (house mouse)	Potency	54.5935	0.0060	38.0041	19,952.5996	AID1159521
GLI family zinc finger 3	Homo sapiens (human)	Potency	0.2173	0.0007	14.5928	83.7951	AID1259369
nuclear receptor subfamily 1, group I, member 3	Homo sapiens (human)	Potency	47.8777	0.0010	22.6508	76.6163	AID1224838; AID1224839; AID1224893
glucocorticoid receptor [Homo sapiens]	Homo sapiens (human)	Potency	43.7533	0.0002	14.3764	60.0339	AID720692
estrogen-related nuclear receptor alpha	Homo sapiens (human)	Potency	0.0971	0.0015	30.6073	15,848.9004	AID1224841
nuclear factor of kappa light polypeptide gene enhancer in B-cells 1 (p105), isoform CRA_a	Homo sapiens (human)	Potency	9.7952	19.7391	45.9784	64.9432	AID1159509
nuclear factor erythroid 2-related factor 2 isoform 1	Homo sapiens (human)	Potency	19.3705	0.0006	27.2152	1,122.0200	AID743219
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Chain A, Proto-oncogene Tyrosine-protein Kinase Src	Homo sapiens (human)	IC50 (µMol)	40,000.0000	3,500.0000	30,875.0000	40,000.0000	AID977608
Chain A, Proto-oncogene Tyrosine-protein Kinase Src	Homo sapiens (human)	IC50 (µMol)	40,000.0000	3,500.0000	30,875.0000	40,000.0000	AID977608
Chain A, Proto-oncogene Tyrosine-protein Kinase Src	Homo sapiens (human)	IC50 (µMol)	40,000.0000	3,500.0000	30,875.0000	40,000.0000	AID977608
Chain A, Proto-oncogene Tyrosine-protein Kinase Src	Homo sapiens (human)	IC50 (µMol)	40,000.0000	3,500.0000	30,875.0000	40,000.0000	AID977608
Chain A, Proto-oncogene Tyrosine-protein Kinase Src	Homo sapiens (human)	IC50 (µMol)	40,000.0000	3,500.0000	30,875.0000	40,000.0000	AID977608
Chain A, Proto-oncogene Tyrosine-protein Kinase Src	Homo sapiens (human)	IC50 (µMol)	40,000.0000	3,500.0000	30,875.0000	40,000.0000	AID977608
Chain A, Proto-oncogene Tyrosine-protein Kinase Src	Homo sapiens (human)	IC50 (µMol)	40,000.0000	3,500.0000	30,875.0000	40,000.0000	AID977608
Chain A, Proto-oncogene Tyrosine-protein Kinase Src	Homo sapiens (human)	IC50 (µMol)	40,000.0000	3,500.0000	30,875.0000	40,000.0000	AID977608
Chain A, Proto-oncogene Tyrosine-protein Kinase Src	Homo sapiens (human)	IC50 (µMol)	40,000.0000	3,500.0000	30,875.0000	40,000.0000	AID977608
Chain A, Proto-oncogene Tyrosine-protein Kinase Src	Homo sapiens (human)	IC50 (µMol)	40,000.0000	3,500.0000	30,875.0000	40,000.0000	AID977608
Chain A, Proto-oncogene Tyrosine-protein Kinase Src	Homo sapiens (human)	IC50 (µMol)	40,000.0000	3,500.0000	30,875.0000	40,000.0000	AID977608
Chain A, Proto-oncogene Tyrosine-protein Kinase Src	Homo sapiens (human)	IC50 (µMol)	40,000.0000	3,500.0000	30,875.0000	40,000.0000	AID977608
Chain A, Proto-oncogene Tyrosine-protein Kinase Src	Homo sapiens (human)	IC50 (µMol)	40,000.0000	3,500.0000	30,875.0000	40,000.0000	AID977608
Chain A, Proto-oncogene Tyrosine-protein Kinase Src	Homo sapiens (human)	IC50 (µMol)	40,000.0000	3,500.0000	30,875.0000	40,000.0000	AID977608
Chain A, Proto-oncogene Tyrosine-protein Kinase Src	Homo sapiens (human)	IC50 (µMol)	40,000.0000	3,500.0000	30,875.0000	40,000.0000	AID977608
Chain A, Proto-oncogene Tyrosine-protein Kinase Src	Homo sapiens (human)	IC50 (µMol)	40,000.0000	3,500.0000	30,875.0000	40,000.0000	AID977608
Chain A, Proto-oncogene Tyrosine-protein Kinase Src	Homo sapiens (human)	IC50 (µMol)	40,000.0000	3,500.0000	30,875.0000	40,000.0000	AID977608
Chain A, Proto-oncogene Tyrosine-protein Kinase Src	Homo sapiens (human)	IC50 (µMol)	40,000.0000	3,500.0000	30,875.0000	40,000.0000	AID977608
Chain A, Proto-oncogene Tyrosine-protein Kinase Src	Homo sapiens (human)	IC50 (µMol)	40,000.0000	3,500.0000	30,875.0000	40,000.0000	AID977608
Chain A, Proto-oncogene Tyrosine-protein Kinase Src	Homo sapiens (human)	IC50 (µMol)	40,000.0000	3,500.0000	30,875.0000	40,000.0000	AID977608
Chain A, Proto-oncogene Tyrosine-protein Kinase Src	Homo sapiens (human)	IC50 (µMol)	40,000.0000	3,500.0000	30,875.0000	40,000.0000	AID977608
Chain A, Proto-oncogene Tyrosine-protein Kinase Src	Homo sapiens (human)	IC50 (µMol)	40,000.0000	3,500.0000	30,875.0000	40,000.0000	AID977608
Chain A, Proto-oncogene Tyrosine-protein Kinase Src	Homo sapiens (human)	IC50 (µMol)	40,000.0000	3,500.0000	30,875.0000	40,000.0000	AID977608
Chain A, Proto-oncogene Tyrosine-protein Kinase Src	Homo sapiens (human)	IC50 (µMol)	40,000.0000	3,500.0000	30,875.0000	40,000.0000	AID977608
Chain A, Proto-oncogene Tyrosine-protein Kinase Src	Homo sapiens (human)	IC50 (µMol)	40,000.0000	3,500.0000	30,875.0000	40,000.0000	AID977608
Chain A, Proto-oncogene Tyrosine-protein Kinase Src	Homo sapiens (human)	IC50 (µMol)	40,000.0000	3,500.0000	30,875.0000	40,000.0000	AID977608
Chain A, Phosphoenolpyruvate carboxykinase	Gallus gallus (chicken)	Ki	50,000.0000	50,000.0000	50,000.0000	50,000.0000	AID977610
D-aspartate oxidase	Rattus norvegicus (Norway rat)	Ki	1,562.0000	5.8900	5.8900	5.8900	AID1247847
Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)	IC50 (µMol)	40,000.0000	0.0002	0.5335	10.0000	AID1797268; AID224309
D-amino-acid oxidase	Homo sapiens (human)	IC50 (µMol)	10,000.0000	0.0040	1.1199	10.0000	AID1247844; AID726222
D-aspartate oxidase	Mus musculus (house mouse)	Ki	1,220.0000	8.6900	8.6900	8.6900	AID1247848
D-aspartate oxidase	Homo sapiens (human)	IC50 (µMol)	1,117.0000	0.0040	0.3937	0.8550	AID1247843; AID726223
D-aspartate oxidase	Homo sapiens (human)	Ki	153.0000	3.8000	3.8000	3.8000	AID1247846
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
lactate metabolic process	L-lactate dehydrogenase A chain	Homo sapiens (human)
pyruvate metabolic process	L-lactate dehydrogenase A chain	Homo sapiens (human)
glycolytic process	L-lactate dehydrogenase A chain	Homo sapiens (human)
peptidyl-tyrosine phosphorylation	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
primary ovarian follicle growth	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
positive regulation of cytokine production	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
stimulatory C-type lectin receptor signaling pathway	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
negative regulation of inflammatory response to antigenic stimulus	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
signal transduction	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
signal complex assembly	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
epidermal growth factor receptor signaling pathway	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
transforming growth factor beta receptor signaling pathway	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
integrin-mediated signaling pathway	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
spermatogenesis	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
learning or memory	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
response to xenobiotic stimulus	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
response to mechanical stimulus	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
response to acidic pH	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
negative regulation of gene expression	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
regulation of epithelial cell migration	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
positive regulation of epithelial cell migration	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
positive regulation of glucose metabolic process	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
positive regulation of protein processing	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
skeletal muscle cell proliferation	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
positive regulation of smooth muscle cell migration	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
macroautophagy	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
peptidyl-tyrosine phosphorylation	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
regulation of cell-cell adhesion	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
platelet activation	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
forebrain development	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
T cell costimulation	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
negative regulation of protein-containing complex assembly	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
protein destabilization	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
response to nutrient levels	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
negative regulation of telomere maintenance via telomerase	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
cellular response to insulin stimulus	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
regulation of intracellular estrogen receptor signaling pathway	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
positive regulation of integrin activation	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
regulation of toll-like receptor 3 signaling pathway	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
adherens junction organization	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
substrate adhesion-dependent cell spreading	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
positive regulation of dephosphorylation	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
negative regulation of hippo signaling	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
intracellular signal transduction	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
entry of bacterium into host cell	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
osteoclast development	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
cellular response to platelet-derived growth factor stimulus	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
Fc-gamma receptor signaling pathway involved in phagocytosis	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
ERBB2 signaling pathway	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
angiotensin-activated signaling pathway	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
odontogenesis	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
positive regulation of apoptotic process	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
negative regulation of apoptotic process	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
regulation of vascular permeability	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
stress fiber assembly	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
negative regulation of cysteine-type endopeptidase activity involved in apoptotic process	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
transcytosis	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
regulation of bone resorption	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
bone resorption	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
positive regulation of Notch signaling pathway	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
positive regulation of bone resorption	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
positive regulation of Ras protein signal transduction	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
positive regulation of insulin receptor signaling pathway	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
protein autophosphorylation	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
platelet-derived growth factor receptor signaling pathway	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
vascular endothelial growth factor receptor signaling pathway	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
neurotrophin TRK receptor signaling pathway	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
ephrin receptor signaling pathway	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
focal adhesion assembly	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
oogenesis	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
positive regulation of peptidyl-tyrosine phosphorylation	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
progesterone receptor signaling pathway	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
leukocyte migration	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
positive regulation of small GTPase mediated signal transduction	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
positive regulation of protein transport	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
response to mineralocorticoid	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
myoblast proliferation	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
response to electrical stimulus	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
negative regulation of focal adhesion assembly	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
positive regulation of phosphatidylinositol 3-kinase/protein kinase B signal transduction	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
negative regulation of mitochondrial depolarization	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
negative regulation of telomerase activity	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
uterus development	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
branching involved in mammary gland duct morphogenesis	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
regulation of cell projection assembly	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
intestinal epithelial cell development	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
interleukin-6-mediated signaling pathway	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
cellular response to hydrogen peroxide	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
positive regulation of ERK1 and ERK2 cascade	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
response to interleukin-1	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
cellular response to lipopolysaccharide	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
cellular response to peptide hormone stimulus	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
cellular response to progesterone stimulus	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
cellular response to fatty acid	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
cellular response to hypoxia	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
cellular response to fluid shear stress	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
positive regulation of podosome assembly	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
DNA biosynthetic process	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
positive regulation of protein serine/threonine kinase activity	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
regulation of heart rate by cardiac conduction	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
positive regulation of canonical Wnt signaling pathway	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
cell-cell adhesion	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
positive regulation of protein localization to nucleus	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
positive regulation of non-membrane spanning protein tyrosine kinase activity	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
positive regulation of TORC1 signaling	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
positive regulation of vascular associated smooth muscle cell proliferation	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
cellular response to prolactin	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
positive regulation of male germ cell proliferation	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
positive regulation of ovarian follicle development	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
positive regulation of lamellipodium morphogenesis	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
positive regulation of platelet-derived growth factor receptor-beta signaling pathway	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
regulation of early endosome to late endosome transport	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
negative regulation of anoikis	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
negative regulation of extrinsic apoptotic signaling pathway	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
negative regulation of intrinsic apoptotic signaling pathway	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
regulation of caveolin-mediated endocytosis	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
cell differentiation	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
cell adhesion	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
innate immune response	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
protein phosphorylation	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
symbiont entry into host cell	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
proline catabolic process	D-amino-acid oxidase	Homo sapiens (human)
digestion	D-amino-acid oxidase	Homo sapiens (human)
D-amino acid catabolic process	D-amino-acid oxidase	Homo sapiens (human)
D-serine catabolic process	D-amino-acid oxidase	Homo sapiens (human)
dopamine biosynthetic process	D-amino-acid oxidase	Homo sapiens (human)
D-alanine catabolic process	D-amino-acid oxidase	Homo sapiens (human)
D-serine metabolic process	D-amino-acid oxidase	Homo sapiens (human)
neutrophil-mediated killing of gram-negative bacterium	D-amino-acid oxidase	Homo sapiens (human)
insemination	D-aspartate oxidase	Homo sapiens (human)
grooming behavior	D-aspartate oxidase	Homo sapiens (human)
regulation of cell communication	D-aspartate oxidase	Homo sapiens (human)
D-amino acid catabolic process	D-aspartate oxidase	Homo sapiens (human)
hormone metabolic process	D-aspartate oxidase	Homo sapiens (human)
nervous system process	D-aspartate oxidase	Homo sapiens (human)
aspartate catabolic process	D-aspartate oxidase	Homo sapiens (human)
L-serine metabolic process	Serine racemase	Homo sapiens (human)
serine family amino acid metabolic process	Serine racemase	Homo sapiens (human)
response to xenobiotic stimulus	Serine racemase	Homo sapiens (human)
response to organic cyclic compound	Serine racemase	Homo sapiens (human)
response to lipopolysaccharide	Serine racemase	Homo sapiens (human)
pyruvate biosynthetic process	Serine racemase	Homo sapiens (human)
D-serine metabolic process	Serine racemase	Homo sapiens (human)
D-serine biosynthetic process	Serine racemase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
L-lactate dehydrogenase activity	L-lactate dehydrogenase A chain	Homo sapiens (human)
protein binding	L-lactate dehydrogenase A chain	Homo sapiens (human)
identical protein binding	L-lactate dehydrogenase A chain	Homo sapiens (human)
cadherin binding	L-lactate dehydrogenase A chain	Homo sapiens (human)
protein kinase activity	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
protein tyrosine kinase activity	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
non-membrane spanning protein tyrosine kinase activity	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
protein kinase C binding	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
signaling receptor binding	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
insulin receptor binding	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
integrin binding	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
protein binding	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
ATP binding	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
phospholipase activator activity	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
enzyme binding	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
heme binding	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
nuclear estrogen receptor binding	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
SH2 domain binding	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
phospholipase binding	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
transmembrane transporter binding	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
cadherin binding	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
ephrin receptor binding	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
ATPase binding	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
phosphoprotein binding	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
BMP receptor binding	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
connexin binding	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
scaffold protein binding	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
D-amino-acid oxidase activity	D-amino-acid oxidase	Homo sapiens (human)
protein binding	D-amino-acid oxidase	Homo sapiens (human)
identical protein binding	D-amino-acid oxidase	Homo sapiens (human)
FAD binding	D-amino-acid oxidase	Homo sapiens (human)
protein binding	D-aspartate oxidase	Homo sapiens (human)
D-aspartate oxidase activity	D-aspartate oxidase	Homo sapiens (human)
D-glutamate oxidase activity	D-aspartate oxidase	Homo sapiens (human)
FAD binding	D-aspartate oxidase	Homo sapiens (human)
magnesium ion binding	Serine racemase	Homo sapiens (human)
L-serine ammonia-lyase activity	Serine racemase	Homo sapiens (human)
calcium ion binding	Serine racemase	Homo sapiens (human)
protein binding	Serine racemase	Homo sapiens (human)
ATP binding	Serine racemase	Homo sapiens (human)
D-serine ammonia-lyase activity	Serine racemase	Homo sapiens (human)
glycine binding	Serine racemase	Homo sapiens (human)
threonine racemase activity	Serine racemase	Homo sapiens (human)
PDZ domain binding	Serine racemase	Homo sapiens (human)
pyridoxal phosphate binding	Serine racemase	Homo sapiens (human)
serine racemase activity	Serine racemase	Homo sapiens (human)
identical protein binding	Serine racemase	Homo sapiens (human)
protein homodimerization activity	Serine racemase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
nucleus	L-lactate dehydrogenase A chain	Homo sapiens (human)
cytosol	L-lactate dehydrogenase A chain	Homo sapiens (human)
membrane	L-lactate dehydrogenase A chain	Homo sapiens (human)
extracellular exosome	L-lactate dehydrogenase A chain	Homo sapiens (human)
oxidoreductase complex	L-lactate dehydrogenase A chain	Homo sapiens (human)
mitochondrion	L-lactate dehydrogenase A chain	Homo sapiens (human)
podosome	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
nucleoplasm	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
cytoplasm	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
mitochondrion	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
mitochondrial inner membrane	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
lysosome	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
late endosome	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
cytosol	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
actin filament	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
plasma membrane	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
caveola	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
focal adhesion	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
cell junction	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
ruffle membrane	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
neuronal cell body	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
dendritic growth cone	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
membrane raft	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
perinuclear region of cytoplasm	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
extracellular exosome	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
synaptic membrane	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
glutamatergic synapse	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
postsynaptic specialization, intracellular component	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
dendritic filopodium	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
plasma membrane	Proto-oncogene tyrosine-protein kinase Src	Homo sapiens (human)
mitochondrial outer membrane	D-amino-acid oxidase	Homo sapiens (human)
extracellular region	D-amino-acid oxidase	Homo sapiens (human)
cytoplasm	D-amino-acid oxidase	Homo sapiens (human)
peroxisomal matrix	D-amino-acid oxidase	Homo sapiens (human)
cytosol	D-amino-acid oxidase	Homo sapiens (human)
cell projection	D-amino-acid oxidase	Homo sapiens (human)
presynaptic active zone	D-amino-acid oxidase	Homo sapiens (human)
cytoplasm	D-amino-acid oxidase	Homo sapiens (human)
peroxisome	D-aspartate oxidase	Homo sapiens (human)
peroxisome	D-aspartate oxidase	Homo sapiens (human)
peroxisomal matrix	D-aspartate oxidase	Homo sapiens (human)
cytosol	D-aspartate oxidase	Homo sapiens (human)
cytoplasm	D-aspartate oxidase	Homo sapiens (human)
cytoplasm	Serine racemase	Homo sapiens (human)
cytosol	Serine racemase	Homo sapiens (human)
neuronal cell body	Serine racemase	Homo sapiens (human)
apical part of cell	Serine racemase	Homo sapiens (human)
cytoplasm	Serine racemase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Assay ID	Title	Year	Journal	Article
AID1246864	Inhibition of human recombinant serine racemase expressed in Escherichia coli Rosetta 2 (DE3) cells using L-serine as substrate by horseradish peroxidase based couple assay	2015	Bioorganic & medicinal chemistry letters, Oct-01, Volume: 25, Issue:19	Expanding the chemical space of human serine racemase inhibitors.
AID1247858	Inhibition of HA-tagged human DDO expressed in human HeLa cells assessed as increase of L-Asp level at 1000 uM after 24 hrs by HPLC analysis	2015	Journal of medicinal chemistry, Sep-24, Volume: 58, Issue:18	Identification of Novel D-Aspartate Oxidase Inhibitors by in Silico Screening and Their Functional and Structural Characterization in Vitro.
AID1247855	Effect on L-Asp level in human HeLa cells at 1000 uM after 24 hrs by HPLC analysis	2015	Journal of medicinal chemistry, Sep-24, Volume: 58, Issue:18	Identification of Novel D-Aspartate Oxidase Inhibitors by in Silico Screening and Their Functional and Structural Characterization in Vitro.
AID1449688	Cytotoxicity against HEK293 cells harboring pendrin P123S mutant after 72 hrs by MTT assay	2017	Bioorganic & medicinal chemistry, 05-01, Volume: 25, Issue:9	Discovery of (2-aminophenyl)methanol as a new molecular chaperone that rescues the localization of P123S mutant pendrin stably expressed in HEK293 cells.
AID429166	Inhibition of wild type human recombinant mitochondrial NADP-ME expressed in Escherichia coli BL21 assessed as residual enzyme activity by spectrophotometry in absence of fumarate	2009	Bioorganic & medicinal chemistry, Aug-01, Volume: 17, Issue:15	Effects of structural analogues of the substrate and allosteric regulator of the human mitochondrial NAD(P)+-dependent malic enzyme.
AID1247850	Effect on D-Asp level in human HeLa cells at 1000 uM after 24 hrs by HPLC analysis	2015	Journal of medicinal chemistry, Sep-24, Volume: 58, Issue:18	Identification of Novel D-Aspartate Oxidase Inhibitors by in Silico Screening and Their Functional and Structural Characterization in Vitro.
AID1246863	Inhibition of hexa-His-tagged purified human recombinant serine racemase expressed in Escherichia coli BL21 Codonplus (DE3)-RIL cells assessed as reduction in beta-elimination of L-serine at by spectrophotomtery	2015	Bioorganic & medicinal chemistry letters, Oct-01, Volume: 25, Issue:19	Expanding the chemical space of human serine racemase inhibitors.
AID726220	Inhibition of human recombinant N-terminal His-tagged serine racemase expressed in Escherichia coli BL21(DE3) using L-serine as substrate after 10 mins by fluorescence assay	2013	Journal of medicinal chemistry, Mar-14, Volume: 56, Issue:5	Identification of novel D-amino acid oxidase inhibitors by in silico screening and their functional characterization in vitro.
AID1246862	Inhibition of hexa-His-tagged purified human recombinant serine racemase expressed in Escherichia coli BL21 Codonplus (DE3)-RIL cells assessed as reduction in beta-elimination of L-serine at 330 uM by spectrophotomtery	2015	Bioorganic & medicinal chemistry letters, Oct-01, Volume: 25, Issue:19	Expanding the chemical space of human serine racemase inhibitors.
AID1174257	Inhibition of mouse serine racemase by Lineweaver-Burk plot	2015	European journal of medicinal chemistry, Jan-07, Volume: 89	Malonate-based inhibitors of mammalian serine racemase: kinetic characterization and structure-based computational study.
AID1453915	Inhibition of human serine racemase C2D2 mutant assessed as remaining enzyme activity by measuring D-serine production using L-serine as substrate incubated for > 8 hrs	2017	Bioorganic & medicinal chemistry, 07-15, Volume: 25, Issue:14	A novel serine racemase inhibitor suppresses neuronal over-activation in vivo.
AID233504	Ionization constant (pKa2) by treating potentiometric titration data according to the method Noyes	1996	Journal of medicinal chemistry, Mar-01, Volume: 39, Issue:5	4'-O-[2-(2-fluoromalonyl)]-L-tyrosine: a phosphotyrosyl mimic for the preparation of signal transduction inhibitory peptides.
AID429164	Inhibition of human mitochondrial NADP-ME E59L mutant expressed in Escherichia coli XL-1 assessed as residual enzyme activity by spectrophotometry in presence of fumarate	2009	Bioorganic & medicinal chemistry, Aug-01, Volume: 17, Issue:15	Effects of structural analogues of the substrate and allosteric regulator of the human mitochondrial NAD(P)+-dependent malic enzyme.
AID1247844	Inhibition of human recombinant DAO expressed in Escherichia coli BL21(DE3) using D-Asp and D-Ala assessed as 2-oxo acid production after 10 mins by colorimetric assay	2015	Journal of medicinal chemistry, Sep-24, Volume: 58, Issue:18	Identification of Novel D-Aspartate Oxidase Inhibitors by in Silico Screening and Their Functional and Structural Characterization in Vitro.
AID1174256	Inhibition of mouse serine racemase using L-serine substrate by reversed-phase HPLC analysis	2015	European journal of medicinal chemistry, Jan-07, Volume: 89	Malonate-based inhibitors of mammalian serine racemase: kinetic characterization and structure-based computational study.
AID1247845	Competitive inhibition of human recombinant DDO expressed in Escherichia coli BL21(DE3) using D-Asp by Lineweaver-Burk plot analysis	2015	Journal of medicinal chemistry, Sep-24, Volume: 58, Issue:18	Identification of Novel D-Aspartate Oxidase Inhibitors by in Silico Screening and Their Functional and Structural Characterization in Vitro.
AID1449696	Chaperone activity at recombinant human C-terminal FLAG-tagged pendrin P123S mutant expressed in HEK293 cells assessed as increase in localization of protein mutant in plasma membrane at 1 to 30 mM after 12 hrs by DAPI staining based immunofluorescence mi	2017	Bioorganic & medicinal chemistry, 05-01, Volume: 25, Issue:9	Discovery of (2-aminophenyl)methanol as a new molecular chaperone that rescues the localization of P123S mutant pendrin stably expressed in HEK293 cells.
AID1247846	Binding affinity to human recombinant DDO	2015	Journal of medicinal chemistry, Sep-24, Volume: 58, Issue:18	Identification of Novel D-Aspartate Oxidase Inhibitors by in Silico Screening and Their Functional and Structural Characterization in Vitro.
AID1185880	Binding affinity to serine recemase (unknown origin)	2014	Bioorganic & medicinal chemistry letters, Aug-15, Volume: 24, Issue:16	In silico and pharmacological screenings identify novel serine racemase inhibitors.
AID726223	Inhibition of human recombinant N-terminal His-tagged DDO expressed in Escherichia coli BL21(DE3) using D-aspartate as substrate by colorimetric assay	2013	Journal of medicinal chemistry, Mar-14, Volume: 56, Issue:5	Identification of novel D-amino acid oxidase inhibitors by in silico screening and their functional characterization in vitro.
AID1185878	Inhibition of full length human recombinant serine recemase C2DC6D mutant expressed in Escherichia coli BL21 (DE3) assessed as D-serine production after 10 mins by Saccharomyces cerevisiae Dsd1SC based D-serine detection assay	2014	Bioorganic & medicinal chemistry letters, Aug-15, Volume: 24, Issue:16	In silico and pharmacological screenings identify novel serine racemase inhibitors.
AID443635	Inhibition of mouse recombinant serine racemase transfected in bacterial expression system	2009	Journal of medicinal chemistry, Oct-08, Volume: 52, Issue:19	Hydroxamic acids as a novel family of serine racemase inhibitors: mechanistic analysis reveals different modes of interaction with the pyridoxal-5'-phosphate cofactor.
AID726222	Inhibition of human recombinant N-terminal His-tagged DAO expressed in Escherichia coli BL21(DE3) using D-serine as substrate by colorimetric assay	2013	Journal of medicinal chemistry, Mar-14, Volume: 56, Issue:5	Identification of novel D-amino acid oxidase inhibitors by in silico screening and their functional characterization in vitro.
AID726218	Binding affinity to human recombinant N-terminal His-tagged DAO expressed in Escherichia coli BL21(DE3) at 40 uM after 2 to 30 mins by absorption spectra analysis	2013	Journal of medicinal chemistry, Mar-14, Volume: 56, Issue:5	Identification of novel D-amino acid oxidase inhibitors by in silico screening and their functional characterization in vitro.
AID224309	Inhibitory activity against SH2 domain of human p60 c-Src tyrosine kinase using surface plasmon resonance (SPR) assay.	2003	Journal of medicinal chemistry, Nov-20, Volume: 46, Issue:24	Requirements for specific binding of low affinity inhibitor fragments to the SH2 domain of (pp60)Src are identical to those for high affinity binding of full length inhibitors.
AID1247843	Inhibition of human recombinant DDO expressed in Escherichia coli BL21(DE3) using D-Asp and D-Ala assessed as 2-oxo acid production after 10 mins by colorimetric assay	2015	Journal of medicinal chemistry, Sep-24, Volume: 58, Issue:18	Identification of Novel D-Aspartate Oxidase Inhibitors by in Silico Screening and Their Functional and Structural Characterization in Vitro.
AID1247848	Inhibition of mouse recombinant DDO using D-Asp	2015	Journal of medicinal chemistry, Sep-24, Volume: 58, Issue:18	Identification of Novel D-Aspartate Oxidase Inhibitors by in Silico Screening and Their Functional and Structural Characterization in Vitro.
AID429165	Inhibition of human mitochondrial NADP-ME E59L mutant expressed in Escherichia coli XL-1 assessed as residual enzyme activity by spectrophotometry in absence of fumarate	2009	Bioorganic & medicinal chemistry, Aug-01, Volume: 17, Issue:15	Effects of structural analogues of the substrate and allosteric regulator of the human mitochondrial NAD(P)+-dependent malic enzyme.
AID121636	In vivo antileukemic activity against P-388 lymphocytic leukemia in BDF1 male mice at 0.6(mg/kg)/day intraperitoneal dose expressed as T/C	1981	Journal of medicinal chemistry, Aug, Volume: 24, Issue:8	Antitumor agents. 44. Bis(helenalinyl) esters and related derivatives as novel potent antileukemic agents.
AID1247852	Inhibition of HA-tagged human DDO expressed in human HeLa cells assessed as increase of D-Asp level at 1000 uM after 24 hrs by HPLC analysis	2015	Journal of medicinal chemistry, Sep-24, Volume: 58, Issue:18	Identification of Novel D-Aspartate Oxidase Inhibitors by in Silico Screening and Their Functional and Structural Characterization in Vitro.
AID429167	Inhibition of wild type human recombinant mitochondrial NADP-ME expressed in Escherichia coli BL21 assessed as residual enzyme activity by spectrophotometry in presence of fumarate	2009	Bioorganic & medicinal chemistry, Aug-01, Volume: 17, Issue:15	Effects of structural analogues of the substrate and allosteric regulator of the human mitochondrial NAD(P)+-dependent malic enzyme.
AID110256	Antileukemic activity of compound against the P-388 lymphocytic leukemic BDF1 male mice at 0.6(mg/kg)/day, administered intraperitoneally; 11.0/9.66 (Treated/control)	1981	Journal of medicinal chemistry, Aug, Volume: 24, Issue:8	Antitumor agents. 44. Bis(helenalinyl) esters and related derivatives as novel potent antileukemic agents.
AID671895	Binding affinity to 6-His-tagged human LDHA (2 to 322 amino acid residue) expressed in Escherichia coli BL21 (DE3) cells by NMR analysis in presence of NADH	2012	Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7	Design and synthesis of novel lactate dehydrogenase A inhibitors by fragment-based lead generation.
AID1453914	Inhibition of human serine racemase C2D2 mutant assessed as remaining enzyme activity by measuring D-serine production using L-serine as substrate at 1 mM incubated for > 8 hrs	2017	Bioorganic & medicinal chemistry, 07-15, Volume: 25, Issue:14	A novel serine racemase inhibitor suppresses neuronal over-activation in vivo.
AID1247847	Inhibition of rat recombinant DDO using D-Asp	2015	Journal of medicinal chemistry, Sep-24, Volume: 58, Issue:18	Identification of Novel D-Aspartate Oxidase Inhibitors by in Silico Screening and Their Functional and Structural Characterization in Vitro.
AID1185879	Inhibition of full length human recombinant serine recemase C2DC6D mutant expressed in Escherichia coli BL21 (DE3) assessed as D-serine production at 1 mM after 10 mins by Saccharomyces cerevisiae Dsd1SC based D-serine detection assay	2014	Bioorganic & medicinal chemistry letters, Aug-15, Volume: 24, Issue:16	In silico and pharmacological screenings identify novel serine racemase inhibitors.
AID1811	Experimentally measured binding affinity data derived from PDB	2003	Journal of medicinal chemistry, Nov-20, Volume: 46, Issue:24	Requirements for specific binding of low affinity inhibitor fragments to the SH2 domain of (pp60)Src are identical to those for high affinity binding of full length inhibitors.
AID977608	Experimentally measured binding affinity data (IC50) for protein-ligand complexes derived from PDB	2003	Journal of medicinal chemistry, Nov-20, Volume: 46, Issue:24	Requirements for specific binding of low affinity inhibitor fragments to the SH2 domain of (pp60)Src are identical to those for high affinity binding of full length inhibitors.
AID1811	Experimentally measured binding affinity data derived from PDB	2006	Biochemistry, Jul-11, Volume: 45, Issue:27	Structural insights into the mechanism of PEPCK catalysis.
AID977610	Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB	2006	Biochemistry, Jul-11, Volume: 45, Issue:27	Structural insights into the mechanism of PEPCK catalysis.
AID1797268	Scintillation Proximity Assay (SPA) from Article 10.1021/jm020970s: \\Requirements for specific binding of low affinity inhibitor fragments to the SH2 domain of (pp60)Src are identical to those for high affinity binding of full length inhibitors.\\	2003	Journal of medicinal chemistry, Nov-20, Volume: 46, Issue:24	Requirements for specific binding of low affinity inhibitor fragments to the SH2 domain of (pp60)Src are identical to those for high affinity binding of full length inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	208 (24.02)	18.7374
1990's	138 (15.94)	18.2507
2000's	265 (30.60)	29.6817
2010's	211 (24.36)	24.3611
2020's	44 (5.08)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	1 (0.11%)	5.53%
Reviews	11 (1.22%)	6.00%
Case Studies	12 (1.33%)	4.05%
Observational	0 (0.00%)	0.25%
Other	881 (97.35%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
acetylcarnitine Acetylcarnitine: An acetic acid ester of CARNITINE that facilitates movement of ACETYL COA into the matrices of mammalian MITOCHONDRIA during the oxidation of FATTY ACIDS.	1.98	1	0	O-acylcarnitine	human metabolite
2,3-dihydroxybenzoic acid 2,3-dihydroxybenzoic acid: RN given refers to parent cpd. dihydroxybenzoic acid : Any member of the class of hydroxybenzoic acids carrying two phenolic hydroxy groups on the benzene ring and its derivatives.. 2,3-dihydroxybenzoic acid : A dihydroxybenzoic acid that is benzoic acid substituted by hydroxy groups at positions 2 and 3. It occurs naturally in Phyllanthus acidus and in the aquatic fern Salvinia molesta.	2.44	2	0	dihydroxybenzoic acid	human xenobiotic metabolite; plant metabolite
tartronic acid hydroxymalonic acid : A dicarboxylic acid that is malonic acid substituted by a hydroxy group at position 2.	2.51	2	0	dicarboxylic acid; dicarboxylic fatty acid	plant metabolite
protocatechuic acid protocatechuic acid: RN given refers to parent cpd; structure. 3,4-dihydroxybenzoic acid : A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4.	2.15	1	0	catechols; dihydroxybenzoic acid	antineoplastic agent; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor; human xenobiotic metabolite; plant metabolite
3-chloroalanine 3-chloroalanine: RN given refers to parent cpd without isomeric designation. 3-chloroalanine : A chloroalanine obtained by replacement of one of the methyl hydrogens of alanine by a chloro group.	1.98	1	0	chloroalanine; non-proteinogenic alpha-amino acid; organochlorine compound
acetoacetic acid acetoacetic acid : A 3-oxo monocarboxylic acid that is butyric acid bearing a 3-oxo substituent.	1.96	1	0	3-oxo fatty acid; ketone body	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.	3.94	13	0	amino acid zwitterion; gamma-amino acid; monocarboxylic acid	human metabolite; neurotransmitter; Saccharomyces cerevisiae metabolite; signalling molecule
4-hydroxybenzaldehyde [no description available]	2.05	1	0	hydroxybenzaldehyde	EC 1.14.17.1 (dopamine beta-monooxygenase) inhibitor; mouse metabolite; plant metabolite
4-hydroxybenzoic acid 4-hydroxybenzoic acid : A monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring.	2.11	1	0	monohydroxybenzoic acid	algal metabolite; plant metabolite
aminolevulinic acid Aminolevulinic Acid: A compound produced from succinyl-CoA and GLYCINE as an intermediate in heme synthesis. It is used as a PHOTOCHEMOTHERAPY for actinic KERATOSIS.. 5-aminolevulinic acid : The simplest delta-amino acid in which the hydrogens at the gamma position are replaced by an oxo group. It is metabolised to protoporphyrin IX, a photoactive compound which accumulates in the skin. Used (in the form of the hydrochloride salt)in combination with blue light illumination for the treatment of minimally to moderately thick actinic keratosis of the face or scalp.	1.98	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-aminovaleric acid 5-aminovaleric acid: from red fox anal secretion; RN given refers to parent cpd. 5-aminopentanoic acid : A delta-amino acid comprising pentanoic acid with an amino substituent at C-5; a methylene homologue of gamma-aminobutyric acid (GABA) that is a weak GABA agonist.	2.25	1	0	amino acid zwitterion; delta-amino acid; omega-amino fatty acid	human metabolite
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.	4.01	14	0	monocarboxylic acid	antimicrobial food preservative; Daphnia magna metabolite; food acidity regulator; protic solvent
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	1.96	1	0	ketone body; methyl ketone; propanones; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; human metabolite; polar aprotic solvent
adipic acid adipic acid : An alpha,omega-dicarboxylic acid that is the 1,4-dicarboxy derivative of butane.	3.31	6	0	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	food acidity regulator; human xenobiotic metabolite
ammonium hydroxide azane : Saturated acyclic nitrogen hydrides having the general formula NnHn+2.	3.08	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.	2.15	1	0	aminobenzoic acid	human metabolite; mouse metabolite
beta-alanine [no description available]	2.43	2	0	amino acid zwitterion; beta-amino acid	agonist; fundamental metabolite; human metabolite; inhibitor; neurotransmitter
benzoic acid Benzoic Acid: A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid.. benzoic acid : A compound comprising a benzene ring core carrying a carboxylic acid substituent.. aromatic carboxylic acid : Any carboxylic acid in which the carboxy group is directly bonded to an aromatic ring.	2.79	3	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
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)	3.75	10	0	halide anion; monoatomic bromine
1-butanol 1-Butanol: A four carbon linear hydrocarbon that has a hydroxy group at position 1.. butan-1-ol : A primary alcohol that is butane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It it produced in small amounts in humans by the gut microbes.	1.98	1	0	alkyl alcohol; primary alcohol; short-chain primary fatty alcohol	human metabolite; mouse metabolite; protic solvent
butyric acid Butyric Acid: A four carbon acid, CH3CH2CH2COOH, with an unpleasant odor that occurs in butter and animal fat as the glycerol ester.. butyrate : A short-chain fatty acid anion that is the conjugate base of butyric acid, obtained by deprotonation of the carboxy group.. butyric acid : A straight-chain saturated fatty acid that is butane in which one of the terminal methyl groups has been oxidised to a carboxy group.	2.38	2	0	fatty acid 4:0; straight-chain saturated fatty acid	human urinary metabolite; Mycoplasma genitalium metabolite
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.	3.09	5	0	monocarboxylic acid	antibacterial agent; astringent; metabolite; protic solvent; solvent
aminooxyacetic acid Aminooxyacetic Acid: A compound that inhibits aminobutyrate aminotransferase activity in vivo, thereby raising the level of gamma-aminobutyric acid in tissues.. (aminooxy)acetic acid : A member of the class of hydroxylamines that is acetic acid substituted at postion 2 by an aminooxy group. It is a compound which inhibits aminobutyrate aminotransferase activity in vivo, resulting in increased levels of gamma-aminobutyric acid in tissues.	2.38	2	0	amino acid; hydroxylamines; monocarboxylic acid	anticonvulsant; EC 2.6.1.19 (4-aminobutyrate--2-oxoglutarate transaminase) inhibitor; EC 4.2.1.22 (cystathionine beta-synthase) inhibitor; nootropic agent
carnitine [no description available]	3.26	6	0	amino-acid betaine	human metabolite; mouse metabolite
catechol [no description available]	2.03	1	0	catechols	allelochemical; genotoxin; plant metabolite
choline [no description available]	8.63	8	0	cholines	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter; nutrient; plant metabolite; Saccharomyces cerevisiae metabolite
aconitic acid Aconitic Acid: A tricarboxylic acid with the formula (COOH)-CH2-C(COOH)=CH-COOH.. aconitic acid : A tricarboxylic acid that is prop-1-ene substituted by carboxy groups at positions 1, 2 and 3.	1.92	1	0	tricarboxylic acid
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.	4.44	22	0	tricarboxylic acid	antimicrobial agent; chelator; food acidity regulator; fundamental metabolite
chlorine chloride : A halide anion formed when chlorine picks up an electron to form an an anion.	3.71	10	0	halide anion; monoatomic chlorine	cofactor; Escherichia coli metabolite; human metabolite
hydrochloric acid Hydrochloric Acid: A strong corrosive acid that is commonly used as a laboratory reagent. It is formed by dissolving hydrogen chloride in water. GASTRIC ACID is the hydrochloric acid component of GASTRIC JUICE.. hydrogen chloride : A mononuclear parent hydride consisting of covalently bonded hydrogen and chlorine atoms.	2.58	2	0	chlorine molecular entity; gas molecular entity; hydrogen halide; mononuclear parent hydride	mouse metabolite
salicylic acid Scalp: The outer covering of the calvaria. It is composed of several layers: SKIN; subcutaneous connective tissue; the occipitofrontal muscle which includes the tendinous galea aponeurotica; loose connective tissue; and the pericranium (the PERIOSTEUM of the SKULL).	2.94	4	0	monohydroxybenzoic acid	algal metabolite; antifungal agent; antiinfective agent; EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor; keratolytic drug; plant hormone; plant metabolite
octane Octanes: Eight-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives.. octane : A straight chain alkane composed of 8 carbon atoms.	2.43	2	0	alkane	xenobiotic
4-nitrophenylphosphate nitrophenylphosphate: RN given refers to mono(4-nitrophenyl) ester of phosphoric acid. 4-nitrophenyl phosphate : An aryl phosphate resulting from the mono-esterification of phosphoric acid with 4-nitrophenol.	2.08	1	0	aryl phosphate	mouse metabolite
octanoic acid octanoic acid: RN given refers to parent cpd; structure in Merck Index, 9th ed, #1764. octanoic acid : A straight-chain saturated fatty acid that is heptane in which one of the hydrogens of a terminal methyl group has been replaced by a carboxy group. Octanoic acid is also known as caprylic acid.	2.36	2	0	medium-chain fatty acid; straight-chain saturated fatty acid	antibacterial agent; Escherichia coli metabolite; human metabolite
3-hydroxybutyric acid 3-Hydroxybutyric Acid: BUTYRIC ACID substituted in the beta or 3 position. It is one of the ketone bodies produced in the liver.. 3-hydroxybutyric acid : A straight-chain 3-hydroxy monocarboxylic acid comprising a butyric acid core with a single hydroxy substituent in the 3- position; a ketone body whose levels are raised during ketosis, used as an energy source by the brain during fasting in humans. Also used to synthesise biodegradable plastics.	2.89	4	0	(omega-1)-hydroxy fatty acid; 3-hydroxy monocarboxylic acid; hydroxybutyric acid	human metabolite
methylmalonic acid Methylmalonic Acid: A malonic acid derivative which is a vital intermediate in the metabolism of fat and protein. Abnormalities in methylmalonic acid metabolism lead to methylmalonic aciduria. This metabolic disease is attributed to a block in the enzymatic conversion of methylmalonyl CoA to succinyl CoA.. methylmalonic acid : A dicarboxylic acid that is malonic acid in which one of the methylene hydrogens is substituted by a methyl group.	5.56	22	0	C4-dicarboxylic acid	human metabolite
2-methylcitric acid 2-methylcitric acid: RN given refers to parent cpd	2.42	2	0	tricarboxylic acid
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.	4.61	27	0	2-hydroxydicarboxylic acid; C4-dicarboxylic acid	food acidity regulator; fundamental metabolite
phosphonoacetic acid Phosphonoacetic Acid: A simple organophosphorus compound that inhibits DNA polymerase, especially in viruses and is used as an antiviral agent.. phosphonoacetic acid : A member of the class of phosphonic acids that is phosphonic acid in which the hydrogen attached to the phosphorous is replaced by a carboxymethyl group.	1.99	1	0	monocarboxylic acid; phosphonic acids	antiviral agent; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor
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.	3.26	6	0	catechols; dihydroxyphenylacetic acid	human metabolite
creatine [no description available]	2.4	2	0	glycine derivative; guanidines; zwitterion	geroprotector; human metabolite; mouse metabolite; neuroprotective agent; nutraceutical
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.	8.93	13	0	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
formaldehyde paraform: polymerized formaldehyde; RN given refers to parent cpd; used in root canal therapy	2.05	1	0	aldehyde; one-carbon compound	allergen; carcinogenic agent; disinfectant; EC 3.5.1.4 (amidase) inhibitor; environmental contaminant; Escherichia coli metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
glutaric acid glutaric acid: RN given refers to parent cpd. glutaric acid : An alpha,omega-dicarboxylic acid that is a linear five-carbon dicarboxylic acid.	4.14	15	0	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	Daphnia magna metabolite; human metabolite
glycine [no description available]	4.63	8	0	alpha-amino acid; amino acid zwitterion; proteinogenic amino acid; serine family amino acid	EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor; fundamental metabolite; hepatoprotective agent; micronutrient; neurotransmitter; NMDA receptor agonist; nutraceutical
glycerol Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.	2.68	3	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.	2.45	2	0	2-hydroxy monocarboxylic acid; primary alcohol	keratolytic drug; metabolite
glyoxylic acid glyoxylic acid: RN given refers to parent cpd. glyoxylic acid : A 2-oxo monocarboxylic acid that is acetic acid bearing an oxo group at the alpha carbon atom.	2.17	1	0	2-oxo monocarboxylic acid; aldehydic acid	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae 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	2.03	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.	3.34	7	0	carbon oxoanion	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
histamine [no description available]	2.35	2	0	aralkylamino compound; imidazoles	human metabolite; mouse metabolite; neurotransmitter
hydrogen Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.	2.65	3	0	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
hydroquinone [no description available]	2.05	1	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.	2.67	3	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.	2.7	3	0	imidazole
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..	3.92	12	0	diatomic iodine	nutrient
itaconic acid itaconic acid : A dicarboxylic acid that is methacrylic acid in which one of the methyl hydrogens is substituted by a carboxylic acid group.	2.13	1	0	dicarboxylic acid; dicarboxylic fatty acid; olefinic compound	fungal metabolite; 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.	1.98	1	0	piperidinemonocarboxylic acid
lactaldehyde lactaldehyde : A member of the class of propanals obtained by the reduction of the carboxylic group of lactic acid (2-hydroxypropanoic acid).	1.98	1	0	hydroxyaldehyde; propanals	mouse metabolite
thioctic acid Thioctic Acid: An octanoic acid bridged with two sulfurs so that it is sometimes also called a pentanoic acid in some naming schemes. It is biosynthesized by cleavage of LINOLEIC ACID and is a coenzyme of oxoglutarate dehydrogenase (KETOGLUTARATE DEHYDROGENASE COMPLEX). It is used in DIETARY SUPPLEMENTS.	2.4	2	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.	1.98	1	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.	2.08	1	0	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
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.	2.03	1	0	inositol phosphate
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.	3.17	5	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.	4.89	8	0	pyridine alkaloid; pyridinecarboxamide; vitamin B3	anti-inflammatory agent; antioxidant; cofactor; EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; Escherichia coli metabolite; geroprotector; human urinary metabolite; metabolite; mouse metabolite; neuroprotective agent; Saccharomyces cerevisiae metabolite; Sir2 inhibitor
niacin Niacin: A water-soluble vitamin of the B complex occurring in various animal and plant tissues. It is required by the body for the formation of coenzymes NAD and NADP. It has PELLAGRA-curative, vasodilating, and antilipemic properties.. vitamin B3 : Any member of a group of vitamers that belong to the chemical structural class called pyridines that exhibit biological activity against vitamin B3 deficiency. Vitamin B3 deficiency causes a condition known as pellagra whose symptoms include depression, dermatitis and diarrhea. The vitamers include nicotinic acid and nicotinamide (and their ionized and salt forms).. nicotinic acid : A pyridinemonocarboxylic acid that is pyridine in which the hydrogen at position 3 is replaced by a carboxy group.	2.59	2	0	pyridine alkaloid; pyridinemonocarboxylic acid; vitamin B3	antidote; antilipemic drug; EC 3.5.1.19 (nicotinamidase) inhibitor; Escherichia coli metabolite; human urinary metabolite; metabolite; mouse metabolite; plant metabolite; vasodilator agent
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	3.16	5	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.	2.48	2	0	nitrogen oxoacid	protic solvent; reagent
nitroxyl nitroxyl: hydroxamic acid oxidized to nitroxyl free radical. nitroxyl : A nitrogen oxoacid consisting of an oxygen atom double-bonded to an NH group.	2.02	1	0	nitrogen oxoacid
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)	2.71	3	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species	human metabolite
hydroxypyruvic acid hydroxypyruvic acid: RN given refers to parent cpd. 3-hydroxypyruvic acid : A 2-oxo monocarboxylic acid that is pyruvic acid in which one of the methyl hydrogens is substituted by a hydroxy group. It is an intermediate involved in the glycine and serine metabolism.	2.03	1	0	2-oxo monocarboxylic acid; 3-hydroxy monocarboxylic acid; primary alpha-hydroxy ketone	Escherichia coli metabolite; human metabolite
oxaloacetic acid Oxaloacetic Acid: A dicarboxylic acid ketone that is an important metabolic intermediate of the CITRIC ACID CYCLE. It can be converted to ASPARTIC ACID by ASPARTATE TRANSAMINASE.. oxaloacetic acid : An oxodicarboxylic acid that is succinic acid bearing a single oxo group.	3.15	5	0	C4-dicarboxylic acid; oxo dicarboxylic acid	geroprotector; 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.	4.69	28	0	alpha,omega-dicarboxylic acid	algal metabolite; human metabolite; plant metabolite
oxamic acid Oxamic Acid: Amino-substituted glyoxylic acid derivative.. oxamic acid : A dicarboxylic acid monoamide resulting from the formal condensation of one of the carboxy groups of oxalic acid with ammonia.	2.03	1	0	dicarboxylic acid monoamide	Escherichia coli metabolite
4-nitrophenol 4-nitrophenol: RN given refers to parent cpd. mononitrophenol : A nitrophenol that is phenol carrying a single nitro substituent at unspecified position.. 4-nitrophenol : A member of the class of 4-nitrophenols that is phenol in which the hydrogen that is para to the hydroxy group has been replaced by a nitro group.	2.05	1	0	4-nitrophenols	human xenobiotic metabolite; mouse metabolite
phenylpyruvic acid phenylpyruvic acid: RN given refers to parent cpd. phenylpyruvate : A 2-oxo monocarboxylic acid anion resulting from deprotonation of the carboxy group of either keto- or enol-phenylpyruvic acid.. keto-phenylpyruvic acid : A 2-oxo monocarboxylic acid that is 3-phenylpropanoic acid substituted by an oxo group at position 2. It is an intermediate metabolite in the phenylalanine pathway.	3.49	2	0	2-oxo monocarboxylic acid	chromogenic compound; EC 6.4.1.1 (pyruvate carboxylase) inhibitor; fundamental 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.	2.01	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.	2.4	2	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.	2.02	1	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.	1.93	1	0	pyridinemonocarboxylic acid	human metabolite; MALDI matrix material
propionic acid propionic acid : A short-chain saturated fatty acid comprising ethane attached to the carbon of a carboxy group.	1.98	1	0	saturated fatty acid; short-chain fatty acid	antifungal drug
pyridine azine : An organonitrogen compound of general structure RCH=N-N=CHR or RR'C=N-N=CRR'.	2.01	1	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.	2.72	3	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
pyruvic acid Pyruvic Acid: An intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed). pyruvic acid : A 2-oxo monocarboxylic acid that is the 2-keto derivative of propionic acid. It is a metabolite obtained during glycolysis.	4.82	10	0	2-oxo monocarboxylic acid	cofactor; fundamental 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.	7.42	2	0	pyridinedicarboxylic acid	Escherichia coli metabolite; human metabolite; mouse metabolite; NMDA receptor agonist
thiosulfates Thiosulfates: Inorganic salts of thiosulfuric acid possessing the general formula R2S2O3.. thiosulfate(2-) : A divalent inorganic anion obtained by removal of both protons from thiosulfuric acid.	2.4	2	0	divalent inorganic anion; sulfur oxide; sulfur oxoanion	human metabolite
dithionite Dithionite: Dithionite. The dithionous acid ion and its salts.	2	1	0	sulfur oxide; sulfur oxoanion
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).	2.42	2	0	divalent inorganic anion; sulfur oxide; sulfur oxoanion
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.	10.33	56	0	alpha,omega-dicarboxylic acid; C4-dicarboxylic acid	anti-ulcer drug; fundamental metabolite; micronutrient; nutraceutical; radiation protective agent
succinic semialdehyde succinic semialdehyde: structure	1.97	1	0	aldehydic acid	Escherichia coli metabolite; mouse metabolite
sulfuric acid sulfuric acid : A sulfur oxoacid that consists of two oxo and two hydroxy groups joined covalently to a central sulfur atom.	8.44	7	0	sulfur oxoacid	catalyst
taurine [no description available]	2.05	1	0	amino sulfonic acid; zwitterion	antioxidant; Escherichia coli metabolite; glycine receptor agonist; human metabolite; mouse metabolite; nutrient; radical scavenger; Saccharomyces cerevisiae metabolite
toluene methylbenzene : Any alkylbenzene that is benzene substituted with one or more methyl groups.	2	1	0	methylbenzene; toluenes; volatile organic compound	cholinergic antagonist; fuel additive; neurotoxin; non-polar solvent
uracil 2,4-dihydroxypyrimidine: a urinary biomarker for bipolar disorder	2.25	1	0	pyrimidine nucleobase; pyrimidone	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; prodrug; Saccharomyces cerevisiae 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.	8.52	8	0	isourea; monocarboxylic acid amide; one-carbon compound	Daphnia magna metabolite; Escherichia coli metabolite; fertilizer; flour treatment agent; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
isocitric acid isocitric acid: RN given refers to unlabeled parent cpd. isocitric acid : A tricarboxylic acid that is propan-1-ol with a hydrogen at each of the 3 carbon positions replaced by a carboxy group.	2.34	2	0	secondary alcohol; tricarboxylic acid	fundamental metabolite
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.	2.69	3	0	non-proteinogenic alpha-amino acid
1,10-phenanthroline 1,10-phenanthroline: RN given refers to parent cpd; inhibits Zn-dependent metalloproteinases	7.03	1	0	phenanthroline	EC 2.7.1.1 (hexokinase) inhibitor; EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor
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.	2.42	2	0	oxopurine	adenosine A1 receptor antagonist; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor
pk 11195 PK-11195 : A monocarboxylic acid amide obtained by formal condensation of the carboxy group of 1-(2-chlorophenyl)isoquinoline-3-carboxylic acid with the amino group of sec-butylmethylamine	2.02	1	0	aromatic amide; isoquinolines; monocarboxylic acid amide; monochlorobenzenes	antineoplastic agent
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine: A dopaminergic neurotoxic compound which produces irreversible clinical, chemical, and pathological alterations that mimic those found in Parkinson disease.. 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine : A tetrahydropyridine that is 1,2,3,6-tetrahydropyridine substituted by a methyl group at position 1 and a phenyl group at position 4.	3.1	5	0	methylpyridines; phenylpyridine; tetrahydropyridine	neurotoxin
2,2'-dipyridyl 2,2'-Dipyridyl: A reagent used for the determination of iron.. 2,2'-bipyridine : A bipyridine in which the two pyridine moieties are linked by a bond between positions C-2 and C-2'.	2.71	3	0	bipyridine	chelator; ferroptosis inhibitor
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.	3.59	9	0	dinitrophenol	allergen; antiseptic drug; bacterial xenobiotic metabolite; geroprotector; oxidative phosphorylation inhibitor
2-amino-4-picoline 2-amino-4-picoline: RN given refers to parent cpd	2.05	1	0
n-methyl-3,4-methylenedioxyamphetamine N-Methyl-3,4-methylenedioxyamphetamine: An N-substituted amphetamine analog. It is a widely abused drug classified as a hallucinogen and causes marked, long-lasting changes in brain serotonergic systems. It is commonly referred to as MDMA or ecstasy.. 3,4-methylenedioxymethamphetamine : A member of the class of benzodioxoles that is 1,3-benzodioxole substituted by a 2-(methylamino)propyl group at position 5.	3.12	5	0	amphetamines; benzodioxoles	neurotoxin
amitrole Amitrole: A non-selective post-emergence, translocated herbicide. According to the Seventh Annual Report on Carcinogens (PB95-109781, 1994) this substance may reasonably be anticipated to be a carcinogen. (From Merck Index, 12th ed) It is an irreversible inhibitor of CATALASE, and thus impairs activity of peroxisomes.. amitrole : A member of the class of triazoles that is 1H-1,2,4-triazole substituted by an amino group at position 3. Used to control annual grasses and aquatic weeds (but not on food crops because it causes cancer in laboratory animals). Its use within the EU was banned from September 2017 on the grounds of potential groundwater contamination and risks to aquatic life; there have also been concerns about its endocrine-disrupting properties.	2	1	0	aromatic amine; triazoles	carotenoid biosynthesis inhibitor; EC 1.11.1.6 (catalase) inhibitor; herbicide
3-aminobenzamide [no description available]	2.45	2	0	benzamides; substituted aniline	EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor
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.	4.54	24	0	C-nitro compound	antimycobacterial drug; EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor; mycotoxin; neurotoxin
4-aminopyridine [no description available]	2.05	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.	3.11	5	0	guaiacols; monocarboxylic acid	human metabolite; mouse metabolite
ethylisopropylamiloride ethylisopropylamiloride: structure in first source. ethylisopropylamiloride : A member of the class of pyrazines that is amiloride in which the amino substitutent of the pyrazine ring that is adjacent to the chloro substituent has been substituted by an ethyl group and by an isopropyl group.	1.98	1	0	aromatic amine; guanidines; monocarboxylic acid amide; organochlorine compound; pyrazines; tertiary amino compound	anti-arrhythmia drug; neuroprotective agent; sodium channel blocker
hydroxyindoleacetic acid (5-hydroxyindol-3-yl)acetic acid : A member of the class of indole-3-acetic acids that is indole-3-acetic acid substituted by a hydroxy group at C-5.	2.02	1	0	indole-3-acetic acids	drug metabolite; human metabolite; mouse metabolite
5-methoxytryptamine 5-Methoxytryptamine: Serotonin derivative proposed as potentiator for hypnotics and sedatives.. 5-methoxytryptamine : A member of the class of tryptamines that is the methyl ether derivative of serotonin.	2	1	0	aromatic ether; primary amino compound; tryptamines	5-hydroxytryptamine 2A receptor agonist; 5-hydroxytryptamine 2B receptor agonist; 5-hydroxytryptamine 2C receptor agonist; antioxidant; cardioprotective agent; human metabolite; mouse metabolite; neuroprotective agent; radiation protective agent; serotonergic agonist
7-nitroindazole 7-nitroindazole: an inhibitor of nitric oxide synthase; exhibits anti-nociceptive activity without increasing blood pressure	2.69	3	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.	2.15	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
acetohydroxamic acid acetohydroxamic acid: urease inhibitor. oxime : Compounds of structure R2C=NOH derived from condensation of aldehydes or ketones with hydroxylamine. Oximes from aldehydes may be called aldoximes; those from ketones may be called ketoximes.. N-hydroxyacetimidic acid : A carbohydroximic acid consisting of acetimidic acid having a hydroxy group attached to the imide nitrogen.. acetohydroxamic acid : A member of the class of acetohydroxamic acids that is acetamide in which one of the amino hydrogens has been replaced by a hydroxy group.	2.05	1	0	acetohydroxamic acids; carbohydroximic acid	algal metabolite; EC 3.5.1.5 (urease) inhibitor
alpha-cyano-4-hydroxycinnamate alpha-cyano-4-hydroxycinnamate: specific inhibitor of pyruvate transport in rat liver mitochondria & human erythrocytes; structure	2.38	2	0
alpha-methyltyrosine methyl ester alpha-methyltyrosine methyl ester: RN given refers to parent cpd	2.02	1	0
pimagedine pimagedine: diamine oxidase & nitric oxide synthase inhibitor; an advanced glycosylation end product inhibitor; used in the treatment of diabetic complications; structure. aminoguanidine : A one-carbon compound whose unique structure renders it capable of acting as a derivative of hydrazine, guanidine or formamide.	2.4	2	0	guanidines; one-carbon compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor; EC 1.4.3.4 (monoamine oxidase) inhibitor
p-aminohippuric acid p-Aminohippuric Acid: The glycine amide of 4-aminobenzoic acid. Its sodium salt is used as a diagnostic aid to measure effective renal plasma flow (ERPF) and excretory capacity.. p-aminohippurate : A hippurate that is the conjugate base of p-aminohippuric acid, arising from deprotonation of the carboxy group.. p-aminohippuric acid : An N-acylglycine that is the 4-amino derivative of hippuric acid; used as a diagnostic agent in the measurement of renal plasma flow.	1.93	1	0	N-acylglycine	Daphnia magna metabolite
theophylline [no description available]	7.67	3	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
amobarbital Amobarbital: A barbiturate with hypnotic and sedative properties (but not antianxiety). Adverse effects are mainly a consequence of dose-related CNS depression and the risk of dependence with continued use is high. (From Martindale, The Extra Pharmacopoeia, 30th ed, p565). amobarbital : A member of the class of barbiturates that is pyrimidine-2,4,6(1H,3H,5H)-trione substituted by a 3-methylbutyl and an ethyl group at position 5. Amobarbital has been shown to exhibit sedative and hypnotic properties.	2.44	2	0	barbiturates
aspirin Aspirin: The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5). acetylsalicylate : A benzoate that is the conjugate base of acetylsalicylic acid, arising from deprotonation of the carboxy group.. acetylsalicylic acid : A member of the class of benzoic acids that is salicylic acid in which the hydrogen that is attached to the phenolic hydroxy group has been replaced by an acetoxy group. A non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity.	2.15	1	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
azelaic acid nonanedioic acid : An alpha,omega-dicarboxylic acid that is heptane substituted at positions 1 and 7 by carboxy groups.	2.6	1	0	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	antibacterial agent; antineoplastic agent; dermatologic drug; plant metabolite
barbital 5,5-diethylbarbituric acid : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by two ethyl groups. Formerly used as a hypnotic (sleeping aid).	2.04	1	0	barbiturates	drug allergen
caffeine [no description available]	7.8	3	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
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.	7.53	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
carmustine Carmustine: A cell-cycle phase nonspecific alkylating antineoplastic agent. It is used in the treatment of brain tumors and various other malignant neoplasms. (From Martindale, The Extra Pharmacopoeia, 30th ed, p462) This substance may reasonably be anticipated to be a carcinogen according to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985). (From Merck Index, 11th ed). carmustine : A member of the class of N-nitrosoureas that is 1,3-bis(2-chloroethyl)urea in which one of the nitrogens is substituted by a nitroso group.	2.05	1	0	N-nitrosoureas; organochlorine compound	alkylating agent; antineoplastic agent
carbonyl cyanide m-chlorophenyl hydrazone Carbonyl Cyanide m-Chlorophenyl Hydrazone: A proton ionophore. It is commonly used as an uncoupling agent and inhibitor of photosynthesis because of its effects on mitochondrial and chloroplast membranes.. CCCP : A member of the class of monochlorobenzenes that is benzene substituted by 2-(1,3-dinitrilopropan-2-ylidene)hydrazinyl and chloro groups at positions 1 and 3, respectively. It is a mitochondrial depolarizing agent that induces reactive oxygen species mediated cell death.	2.38	2	0	hydrazone; monochlorobenzenes; nitrile	antibacterial agent; geroprotector; ionophore
cgp 37157 CGP 37157: benzothiazepine derivative of clonazepam; inhibits the in vitro activity of mitochondrial sodium-calcium exchange	1.98	1	0	benzothiazepine
chelerythrine chelerythrine : A benzophenanthridine alkaloid isolated from the root of Zanthoxylum simulans, Chelidonium majus L., and other Papaveraceae.	2.06	1	0	benzophenanthridine alkaloid; organic cation	antibacterial agent; antineoplastic agent; EC 2.7.11.13 (protein kinase C) inhibitor
chloral hydrate [no description available]	1.96	1	0	aldehyde hydrate; ethanediol; organochlorine compound	general anaesthetic; mouse metabolite; sedative; xenobiotic
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.	1.98	1	0	1,4-benzodiazepinone; monochlorobenzenes	anticonvulsant; anxiolytic drug; GABA modulator
cyclocreatine cyclocreatine: structure given in first source	1.99	1	0
cystamine [no description available]	2.06	1	0	organic disulfide; primary amino compound	EC 2.3.2.13 (protein-glutamine gamma-glutamyltransferase) inhibitor
2,3-dimethoxy-5-methyl-6-decyl-1,4-benzoquinone 2,3-dimethoxy-5-methyl-6-decyl-1,4-benzoquinone: ubiquinol analog. 6-decylubiquinone : A member of the class of 1,4-benzoquinones that is 2,3-dimethoxybenzoquinone which has been substituted at positions 5 and 6 by decyl and methyl groups.	2.17	1	0	1,4-benzoquinones	cofactor
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.	2.05	1	0	benzothiadiazine; organochlorine compound; sulfone	antihypertensive agent; beta-adrenergic agonist; bronchodilator agent; cardiotonic drug; diuretic; K-ATP channel agonist; sodium channel blocker; sympathomimetic agent; vasodilator agent
diethyl pyrocarbonate Diethyl Pyrocarbonate: Preservative for wines, soft drinks, and fruit juices and a gentle esterifying agent.. diethyl pyrocarbonate : The diethyl ester of dicarbonic acid.	1.96	1	0	acyclic carboxylic anhydride
diphenyleneiodonium diphenyleneiodonium: structure in first source; NADPH oxidase inhibitor. dibenziodolium : An organic cation that is fluorene in which the methylene group is replaced by a positively charged iodine.	2.31	1	0	organic cation
valproic acid Valproic Acid: A fatty acid with anticonvulsant and anti-manic properties that is used in the treatment of EPILEPSY and BIPOLAR DISORDER. The mechanisms of its therapeutic actions are not well understood. It may act by increasing GAMMA-AMINOBUTYRIC ACID levels in the brain or by altering the properties of VOLTAGE-GATED SODIUM CHANNELS.. valproic acid : A branched-chain saturated fatty acid that comprises of a propyl substituent on a pentanoic acid stem.	2.68	3	0	branched-chain fatty acid; branched-chain saturated fatty acid	anticonvulsant; antimanic drug; EC 3.5.1.98 (histone deacetylase) inhibitor; GABA agent; neuroprotective agent; psychotropic drug; teratogenic agent
racemetirosine alpha-Methyltyrosine: An inhibitor of the enzyme TYROSINE 3-MONOOXYGENASE, and consequently of the synthesis of catecholamines. It is used to control the symptoms of excessive sympathetic stimulation in patients with PHEOCHROMOCYTOMA. (Martindale, The Extra Pharmacopoeia, 30th ed)	2	1	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.	3.09	5	0
eicosapentaenoic acid ethyl ester [no description available]	2.06	1	0
ethylenediamine ethylenediamine: RN given refers to parent cpd; edamine is the recommended contraction for the ethylenediamine radical. ethylenediamine : An alkane-alpha,omega-diamine in which the alkane is ethane.	7.44	2	0	alkane-alpha,omega-diamine	GABA agonist
carbonyl cyanide p-trifluoromethoxyphenylhydrazone Carbonyl Cyanide p-Trifluoromethoxyphenylhydrazone: A proton ionophore that is commonly used as an uncoupling agent in biochemical studies.. carbonyl cyanide p-trifluoromethoxyphenylhydrazone : A hydrazone that is hydrazonomalononitrile in which one of the hydrazine hydrogens is substituted by a p-trifluoromethoxyphenyl group.	2.68	3	0	aromatic ether; hydrazone; nitrile; organofluorine compound	ATP synthase inhibitor; geroprotector; ionophore
felodipine Felodipine: A dihydropyridine calcium antagonist with positive inotropic effects. It lowers blood pressure by reducing peripheral vascular resistance through a highly selective action on smooth muscle in arteriolar resistance vessels.. felodipine : The mixed (methyl, ethyl) diester of 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid. A calcium-channel blocker, it lowers blood pressure by reducing peripheral vascular resistance through a highly selective action on smooth muscle in arteriolar resistance vessels. It is used in the management of hypertension and angina pectoris.	2.15	1	0	dichlorobenzene; dihydropyridine; ethyl ester; methyl ester	anti-arrhythmia drug; antihypertensive agent; calcium channel blocker; vasodilator agent
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.	2.39	2	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.	2.03	1	0	(trifluoromethyl)benzenes; aromatic ether; secondary amino compound
vanoxerine vanoxerine: structure given in first source. vanoxerine : An N-alkylpiperazine that consists of piperazine bearing 2-bis(4-fluorophenyl)methoxy]ethyl and 3-phenylpropyl groups at positions 1 and 4 respectively. Potent, competitive inhibitor of dopamine uptake (Ki = 1 nM for inhibition of striatal dopamine uptake). Has > 100-fold lower affinity for the noradrenalin and 5-HT uptake carriers. Also a potent sigma ligand (IC50 = 48 nM). Centrally active following systemic administration.	2.03	1	0	ether; N-alkylpiperazine; organofluorine compound; tertiary amino compound	dopamine uptake inhibitor
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.	2.71	3	0	dihydroxybenzoic acid	EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; fungal metabolite; human metabolite; MALDI matrix material; mouse metabolite
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.	1.97	1	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.	2.41	1	0	monochlorobenzenes; N-sulfonylurea	anti-arrhythmia drug; EC 2.7.1.33 (pantothenate kinase) inhibitor; EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor; hypoglycemic agent
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.	2.62	3	0	barbiturates
iodoacetamide [no description available]	1.96	1	0
iproniazid [no description available]	1.98	1	0	carbohydrazide; pyridines
isoniazid Hydra: A genus of freshwater polyps in the family Hydridae, order Hydroida, class HYDROZOA. They are of special interest because of their complex organization and because their adult organization corresponds roughly to the gastrula of higher animals.. hydrazide : Compounds derived from oxoacids RkE(=O)l(OH)m (l =/= 0) by replacing -OH by -NRNR2 (R groups are commonly H). (IUPAC).	2.42	2	0	carbohydrazide	antitubercular agent; drug allergen
kynurenic acid Kynurenic Acid: A broad-spectrum excitatory amino acid antagonist used as a research tool.. kynurenic acid : A quinolinemonocarboxylic acid that is quinoline-2-carboxylic acid substituted by a hydroxy group at C-4.	2.02	1	0	monohydroxyquinoline; quinolinemonocarboxylic acid	G-protein-coupled receptor agonist; human metabolite; neuroprotective agent; nicotinic antagonist; NMDA receptor antagonist; Saccharomyces cerevisiae metabolite
lamotrigine [no description available]	2.68	3	0	1,2,4-triazines; dichlorobenzene; primary arylamine	anticonvulsant; antidepressant; antimanic drug; calcium channel blocker; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; environmental contaminant; excitatory amino acid antagonist; geroprotector; non-narcotic analgesic; xenobiotic
memantine [no description available]	1.99	1	0	adamantanes; primary aliphatic amine	antidepressant; antiparkinson drug; dopaminergic agent; neuroprotective agent; NMDA receptor antagonist
mesalamine Mesalamine: An anti-inflammatory agent, structurally related to the SALICYLATES, which is active in INFLAMMATORY BOWEL DISEASE. It is considered to be the active moiety of SULPHASALAZINE. (From Martindale, The Extra Pharmacopoeia, 30th ed). mesalamine : A monohydroxybenzoic acid that is salicylic acid substituted by an amino group at the 5-position.	2.15	1	0	amino acid; aromatic amine; monocarboxylic acid; monohydroxybenzoic acid; phenols	non-steroidal anti-inflammatory drug
metformin Metformin: A biguanide hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. Metformin improves glycemic control by improving insulin sensitivity and decreasing intestinal absorption of glucose. (From Martindale, The Extra Pharmacopoeia, 30th ed, p289). metformin : A member of the class of guanidines that is biguanide the carrying two methyl substituents at position 1.	2.45	2	0	guanidines	environmental contaminant; geroprotector; hypoglycemic agent; xenobiotic
methenamine Methenamine: An anti-infective agent most commonly used in the treatment of urinary tract infections. Its anti-infective action derives from the slow release of formaldehyde by hydrolysis at acidic pH. (From Martindale, The Extra Pharmacopoeia, 30th ed, p173). hexamethylenetetramine : A polycyclic cage that is adamantane in which the carbon atoms at positions 1, 3, 5 and 7 are replaced by nitrogen atoms.	2.01	1	0	polyazaalkane; polycyclic cage; tetramine	antibacterial drug
minoxidil Minoxidil: A potent direct-acting peripheral vasodilator (VASODILATOR AGENTS) that reduces peripheral resistance and produces a fall in BLOOD PRESSURE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p371). minoxidil : A pyrimidine N-oxide that is pyrimidine-2,4-diamine 3-oxide substituted by a piperidin-1-yl group at position 6.	1.99	1	0	dialkylarylamine; tertiary amino compound
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	1	0	alkaloid; isoxazoles; primary amino compound	fungal metabolite; GABA agonist; oneirogen; psychotropic drug
ethylmaleimide Ethylmaleimide: A sulfhydryl reagent that is widely used in experimental biochemical studies.	1.96	1	0	maleimides	anticoronaviral agent; EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor; EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor; EC 2.7.1.1 (hexokinase) inhibitor
clorgyline Clorgyline: An antidepressive agent and monoamine oxidase inhibitor related to PARGYLINE.. clorgyline : An aromatic ether that is the 2,4-dichlorophenyl ether of 3-aminopropan-1-ol in which the nitrogen is substituted by a methyl group and a prop-1-yn-3-yl group. A monoamine oxidase inhibitor, it was formerly used as an antidepressant.	2.7	3	0	aromatic ether; dichlorobenzene; terminal acetylenic compound; tertiary amino compound	antidepressant; EC 1.4.3.4 (monoamine oxidase) inhibitor
nafronyl Nafronyl: A drug used in the management of peripheral and cerebral vascular disorders. It is claimed to enhance cellular oxidative capacity and to be a spasmolytic. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1310) It may also be an antagonist at 5HT-2 serotonin receptors.	1.97	1	0	naphthalenes
nipecotic acid nipecotic acid: RN given refers to cpd without isomeric designation. nipecotic acid : A piperidinemonocarboxylic acid that is piperidine in which one of the hydrogens at position 3 is substituted by a carboxylic acid group.	2	1	0	beta-amino acid; piperidinemonocarboxylic acid
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).	3.26	6	0	benzenetriol; catecholamine; primary amino compound	drug metabolite; human metabolite; neurotoxin
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.	2.06	1	0	acetylenic compound; carboxylic ester; racemate; tertiary alcohol; tertiary amino compound	antispasmodic drug; calcium channel blocker; local anaesthetic; muscarinic antagonist; muscle relaxant; parasympatholytic
quinone benzoquinone : The simplest members of the class of benzoquinones, consisting of cyclohexadiene which is substituted by two oxo groups.. 1,4-benzoquinone : The simplest member of the class of 1,4-benzoquinones, obtained by the formal oxidation of hydroquinone to the corresponding diketone. It is a metabolite of benzene.. quinone : Compounds having a fully conjugated cyclic dione structure, such as that of benzoquinones, derived from aromatic compounds by conversion of an even number of -CH= groups into -C(=O)- groups with any necessary rearrangement of double bonds (polycyclic and heterocyclic analogues are included).	2.46	2	0	1,4-benzoquinones	cofactor; human xenobiotic metabolite; mouse metabolite
pioglitazone Pioglitazone: A thiazolidinedione and PPAR GAMMA agonist that is used in the treatment of TYPE 2 DIABETES MELLITUS.. pioglitazone : A member of the class of thiazolidenediones that is 1,3-thiazolidine-2,4-dione substituted by a benzyl group at position 5 which in turn is substituted by a 2-(5-ethylpyridin-2-yl)ethoxy group at position 4 of the phenyl ring. It exhibits hypoglycemic activity.	2.05	1	0	aromatic ether; pyridines; thiazolidinediones	antidepressant; cardioprotective agent; EC 2.7.1.33 (pantothenate kinase) inhibitor; EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor; ferroptosis inhibitor; geroprotector; hypoglycemic agent; insulin-sensitizing drug; PPARgamma agonist; xenobiotic
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.	1.96	1	0	inorganic chloride; inorganic potassium salt; potassium salt	fertilizer
propidium Propidium: Quaternary ammonium analog of ethidium; an intercalating dye with a specific affinity to certain forms of DNA and, used as diiodide, to separate them in density gradients; also forms fluorescent complexes with cholinesterase which it inhibits.	2.02	1	0	phenanthridines; quaternary ammonium ion	fluorochrome; intercalator
resorcinol resorcinol: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7951. resorcinol : A benzenediol that is benzene dihydroxylated at positions 1 and 3.	7.05	1	0	benzenediol; phenolic donor; resorcinols	erythropoietin inhibitor; sensitiser
riluzole Riluzole: A glutamate antagonist (RECEPTORS, GLUTAMATE) used as an anticonvulsant (ANTICONVULSANTS) and to prolong the survival of patients with AMYOTROPHIC LATERAL SCLEROSIS.	2.71	3	0	benzothiazoles
rofecoxib [no description available]	7.08	1	0	butenolide; sulfone	analgesic; cyclooxygenase 2 inhibitor; non-steroidal anti-inflammatory drug
rolipram [no description available]	2.04	1	0	pyrrolidin-2-ones	antidepressant; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor
salicyl alcohol salicyl alcohol: RN given refers to parent cpd; saligenin is the aglycone of salicin; structure; it is oxidatively metabolized to gentisic acid. salicyl alcohol : A hydroxybenzyl alcohol that is phenol substituted by a hydroxymethyl group at C-2.	2.15	1	0	aromatic primary alcohol; hydroxybenzyl alcohol	human urinary metabolite
suberoyl bis-hydroxamic acid suberoyl bis-hydroxamic acid: antineoplastic, Histone Deacetylase inhibitor	2.05	1	0	hydroxamic acid
sodium fluoride [no description available]	1.98	1	0	fluoride salt	mutagen
fluoroacetic acid fluoroacetic acid: N1 same as NM; RN given refers to parent cpd. fluoroacetic acid : A haloacetic acid that is acetic acid in which one of the methyl hydrogens is substituted by fluorine.	2.68	3	0	haloacetic acid; organofluorine compound	EC 4.2.1.3 (aconitate hydratase) inhibitor
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.	3.21	6	0	haloacetic acid; organoiodine compound	alkylating agent
vorinostat Vorinostat: A hydroxamic acid and anilide derivative that acts as a HISTONE DEACETYLASE inhibitor. It is used in the treatment of CUTANEOUS T-CELL LYMPHOMA and SEZARY SYNDROME.. vorinostat : A dicarboxylic acid diamide comprising suberic (octanedioic) acid coupled to aniline and hydroxylamine. A histone deacetylase inhibitor, it is marketed under the name Zolinza for the treatment of cutaneous T cell lymphoma (CTCL).	2.05	1	0	dicarboxylic acid diamide; hydroxamic acid	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor
sulpiride Sulpiride: A dopamine D2-receptor antagonist. It has been used therapeutically as an antidepressant, antipsychotic, and as a digestive aid. (From Merck Index, 11th ed). sulpiride : A member of the class of benzamides obtained from formal condensation between the carboxy group of 2-methoxy-5-sulfamoylbenzoic acid and the primary amino group of (1-ethylpyrrolidin-2-yl)methylamine.	2	1	0	benzamides; N-alkylpyrrolidine; sulfonamide	antidepressant; antiemetic; antipsychotic agent; dopaminergic antagonist
3-hydroxyaspartic acid 3-hydroxyaspartic acid: RN given refers to cpd without isomeric designation. 3-hydroxyaspartic acid : A hydroxy-amino acid that is aspartic acid in which one of the methylene hydrogens has been replaced by a hydroxy group.	2.01	1	0	amino dicarboxylic acid; aspartic acid derivative; C4-dicarboxylic acid; hydroxy-amino acid
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.	2.01	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	1.98	1	0	1,3-thiazoles; benzimidazole fungicide; benzimidazoles	antifungal agrochemical; antinematodal drug
2-thiosalicylic acid 2-thiosalicylic acid: a degradation product of thimerosal; RN given refers to parent cpd. thiosalicylic acid : A sulfanylbenzoic acid that is the 2-sulfanyl derivative of benzoic acid.	2.15	1	0	sulfanylbenzoic acid	antipyretic; non-narcotic analgesic
thenoyltrifluoroacetone Thenoyltrifluoroacetone: Chelating agent and inhibitor of cellular respiration.	3.1	5	0
tyrphostin a9 [no description available]	2.4	2	0	alkylbenzene	geroprotector
corticosterone [no description available]	2.13	1	0	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone	human metabolite; mouse metabolite
reserpine Reserpine: An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria. Reserpine inhibits the uptake of norepinephrine into storage vesicles resulting in depletion of catecholamines and serotonin from central and peripheral axon terminals. It has been used as an antihypertensive and an antipsychotic as well as a research tool, but its adverse effects limit its clinical use.. reserpine : An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria.	2.42	2	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
alloxan Alloxan: Acidic compound formed by oxidation of URIC ACID. It is isolated as an efflorescent crystalline hydrate.. alloxan : A member of the class of pyrimidones, the structure of which is that of perhydropyrimidine substituted at C-2, -4, -5 and -6 by oxo groups.	2	1	0	pyrimidone	hyperglycemic agent; metabolite
benzimidazole 1H-benzimidazole : The 1H-tautomer of benzimidazole.	2.06	1	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.	2.42	2	0	4-hydroxyproline; L-alpha-amino acid zwitterion	human metabolite; mouse metabolite; plant metabolite
thyroxine Thyroxine: The major hormone derived from the thyroid gland. Thyroxine is synthesized via the iodination of tyrosines (MONOIODOTYROSINE) and the coupling of iodotyrosines (DIIODOTYROSINE) in the THYROGLOBULIN. Thyroxine is released from thyroglobulin by proteolysis and secreted into the blood. Thyroxine is peripherally deiodinated to form TRIIODOTHYRONINE which exerts a broad spectrum of stimulatory effects on cell metabolism.. thyroxine : An iodothyronine compound having iodo substituents at the 3-, 3'-, 5- and 5'-positions.	1.98	1	0	2-halophenol; iodophenol; L-phenylalanine derivative; non-proteinogenic L-alpha-amino acid; thyroxine zwitterion; thyroxine	antithyroid drug; human metabolite; mouse metabolite; thyroid hormone
aldosterone [no description available]	1.96	1	0	11beta-hydroxy steroid; 18-oxo steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid hormone; mineralocorticoid; primary alpha-hydroxy ketone; steroid aldehyde	human metabolite; mouse metabolite
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.	2.05	1	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.	2.05	1	0	organic heterobicyclic compound; organonitrogen heterocyclic compound
alanine Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.	2.92	4	0	alanine zwitterion; alanine; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid	EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor; fundamental metabolite
serine Serine: A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids.. serine : An alpha-amino acid that is alanine substituted at position 3 by a hydroxy group.	2.96	4	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
chloramphenicol Amphenicol: Chloramphenicol and its derivatives.	2.31	1	0	C-nitro compound; carboxamide; diol; organochlorine compound	antibacterial drug; antimicrobial agent; Escherichia coli metabolite; geroprotector; Mycoplasma genitalium metabolite; protein synthesis inhibitor
aspartic acid Aspartic Acid: One of the non-essential amino acids commonly occurring in the L-form. It is found in animals and plants, especially in sugar cane and sugar beets. It may be a neurotransmitter.. aspartic acid : An alpha-amino acid that consists of succinic acid bearing a single alpha-amino substituent. L-aspartic acid : The L-enantiomer of aspartic acid.	3.37	7	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.	3.23	6	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.	4.09	14	0	aspartate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; lysine; organic molecular entity; proteinogenic amino acid	algal metabolite; anticonvulsant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
cyanides Cyanides: Inorganic salts of HYDROGEN CYANIDE containing the -CN radical. The concept also includes isocyanides. It is distinguished from NITRILES, which denotes organic compounds containing the -CN radical.. cyanides : Salts and C-organyl derivatives of hydrogen cyanide, HC#N.. isocyanide : The isomer HN(+)#C(-) of hydrocyanic acid, HC#N, and its hydrocarbyl derivatives RNC (RN(+)#C(-)).. cyanide : A pseudohalide anion that is the conjugate base of hydrogen cyanide.	3.75	11	0	pseudohalide anion	EC 1.9.3.1 (cytochrome c oxidase) inhibitor
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.	2.02	1	0	sulfamic acids
9,10-dimethyl-1,2-benzanthracene 9,10-Dimethyl-1,2-benzanthracene: Polycyclic aromatic hydrocarbon found in tobacco smoke that is a potent carcinogen.. 7,12-dimethyltetraphene : A tetraphene having methyl substituents at the 7- and 12-positions. It is a potent carcinogen and is present in tobacco smoke.	2.11	1	0	ortho-fused polycyclic arene; tetraphenes	carcinogenic agent
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	1	0	aporphine alkaloid	alpha-adrenergic drug; antidyskinesia agent; antiparkinson drug; dopamine agonist; emetic; serotonergic drug
tetrabenazine 9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one : A benzoquinolizine that is 1,2,3,4,4a,9,10,10a-octahydrophenanthrene in which the carbon at position 10a is replaced by a nitrogen and which is substituted by an isobutyl group at position 2, an oxo group at position 3, and methoxy groups at positions 6 and 7.	2	1	0	benzoquinolizine; cyclic ketone; tertiary amino compound
adenosine diphosphate Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.	3.23	6	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.	2.04	1	0	tetrachlorophenol	xenobiotic metabolite
galactose galactopyranose : The pyranose form of galactose.	2	1	0	D-galactose; galactopyranose	Escherichia coli metabolite; mouse metabolite
carbostyril Quinolones: A group of derivatives of naphthyridine carboxylic acid, quinoline carboxylic acid, or NALIDIXIC ACID.. quinolin-2(1H)-one : A quinolone that is 1,2-dihydroquinoline substituted by an oxo group at position 2.	2.04	1	0	monohydroxyquinoline; quinolone	bacterial xenobiotic metabolite
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	2.42	2	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.	3.24	6	0	ethylenediamine derivative; polyamino carboxylic acid; tetracarboxylic acid	anticoagulant; antidote; chelator; copper chelator; geroprotector
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.	3.73	10	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.	2.4	2	0	amine; thiol	geroprotector; human metabolite; mouse metabolite; radiation protective agent
phlorhizin [no description available]	6.93	1	0	aryl beta-D-glucoside; dihydrochalcones; monosaccharide derivative	antioxidant; plant metabolite
adenosine monophosphate Adenosine Monophosphate: Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position.	2.07	1	0	adenosine 5'-phosphate; purine ribonucleoside 5'-monophosphate	adenosine A1 receptor agonist; cofactor; EC 3.1.3.1 (alkaline phosphatase) inhibitor; EC 3.1.3.11 (fructose-bisphosphatase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
methylene blue Methylene Blue: A compound consisting of dark green crystals or crystalline powder, having a bronze-like luster. Solutions in water or alcohol have a deep blue color. Methylene blue is used as a bacteriologic stain and as an indicator. It inhibits GUANYLATE CYCLASE, and has been used to treat cyanide poisoning and to lower levels of METHEMOGLOBIN.. methylene blue : An organic chloride salt having 3,7-bis(dimethylamino)phenothiazin-5-ium as the counterion. A commonly used dye that also exhibits antioxidant, antimalarial, antidepressant and cardioprotective properties.	6.92	1	0	organic chloride salt	acid-base indicator; antidepressant; antimalarial; antimicrobial agent; antioxidant; cardioprotective agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 4.6.1.2 (guanylate cyclase) inhibitor; fluorochrome; histological dye; neuroprotective agent; physical tracer
leucine Leucine: An essential branched-chain amino acid important for hemoglobin formation.. leucine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isobutyl group.	2.7	3	0	amino acid zwitterion; L-alpha-amino acid; leucine; proteinogenic amino acid; pyruvate family amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
aniline [no description available]	2.04	1	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.	2.01	1	0	2,2-dialkylglycine zwitterion; 2,2-dialkylglycine
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.	7.35	2	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.	2.67	3	0	aspartate family amino acid; L-alpha-amino acid; methionine zwitterion; methionine; proteinogenic amino acid	antidote to paracetamol poisoning; human metabolite; micronutrient; mouse metabolite; nutraceutical
phenylalanine Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.	2.94	4	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; phenylalanine; proteinogenic amino acid	algal metabolite; EC 3.1.3.1 (alkaline phosphatase) inhibitor; Escherichia coli metabolite; human xenobiotic metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
cytidine triphosphate Cytidine Triphosphate: Cytidine 5'-(tetrahydrogen triphosphate). A cytosine nucleotide containing three phosphate groups esterified to the sugar moiety.	1.99	1	0	cytidine 5'-phosphate; pyrimidine ribonucleoside 5'-triphosphate	Escherichia coli metabolite; mouse metabolite
cycloheximide Cycloheximide: Antibiotic substance isolated from streptomycin-producing strains of Streptomyces griseus. It acts by inhibiting elongation during protein synthesis.. cycloheximide : A dicarboximide that is 4-(2-hydroxyethyl)piperidine-2,6-dione in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 3,5-dimethyl-2-oxocyclohexyl group. It is an antibiotic produced by the bacterium Streptomyces griseus.	1.99	1	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.	1.96	1	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.	2.66	3	0	chloromethanes; one-carbon compound	carcinogenic agent; central nervous system drug; inhalation anaesthetic; non-polar solvent; refrigerant
mannitol [no description available]	2.4	2	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
dithionitrobenzoic acid Dithionitrobenzoic Acid: A standard reagent for the determination of reactive sulfhydryl groups by absorbance measurements. It is used primarily for the determination of sulfhydryl and disulfide groups in proteins. The color produced is due to the formation of a thio anion, 3-carboxyl-4-nitrothiophenolate.. dithionitrobenzoic acid : An organic disulfide that results from the formal oxidative dimerisation of 2-nitro-5-thiobenzoic acid. An indicator used to quantify the number or concentration of thiol groups.	1.98	1	0	nitrobenzoic acid; organic disulfide	indicator
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.	1.96	1	0	non-proteinogenic L-alpha-amino acid; ornithine	algal metabolite; hepatoprotective agent; mouse metabolite
dinitrofluorobenzene Dinitrofluorobenzene: Irritants and reagents for labeling terminal amino acid groups.. 1-fluoro-2,4-dinitrobenzene : The organofluorine compound that is benzene with a fluoro substituent at the 1-position and two nitro substituents in the 2- and 4-positions.	1.97	1	0	C-nitro compound; organofluorine compound	agrochemical; allergen; chromatographic reagent; EC 2.7.3.2 (creatine kinase) inhibitor; protein-sequencing agent; spectrophotometric reagent
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.	1.93	1	0	amino acid zwitterion; asparagine; aspartate family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
histidine Histidine: An essential amino acid that is required for the production of HISTAMINE.. L-histidine : The L-enantiomer of the amino acid histidine.. histidine : An alpha-amino acid that is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3.	8.1	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
tryptophan Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3.	2	1	0	erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; tryptophan zwitterion; tryptophan	antidepressant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
arginine Arginine: An essential amino acid that is physiologically active in the L-form.. arginine : An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group.	7.4	2	0	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
ethylene Plastipore: high density polyethylene sponge biocompatible material; used as posts in dental bridges	2.48	2	0	alkene; gas molecular entity	plant hormone; refrigerant
acetylene [no description available]	3.12	5	0	alkyne; gas molecular entity; terminal acetylenic compound
propane Propane: A three carbon alkane with the formula H3CCH2CH3.	2	1	0	alkane; gas molecular entity	food propellant
acetonitrile acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.	7.11	1	0	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
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.	2.25	1	0	gas molecular entity; oxacycle; saturated organic heteromonocyclic parent	allergen; mouse metabolite; mutagen
2-propylamine 2-propylamine: RN given refers to parent cpd	2.1	1	0	alkylamines; primary aliphatic amine
tert-butyl alcohol tert-Butyl Alcohol: An isomer of butanol that contains a tertiary butyl group that consists of three methyl groups, each separately attached to a central (tertiary) carbon.. tert-butanol : A tertiary alcohol alcohol that is isobutane substituted by a hydroxy group at position 2.	2.02	1	0	tertiary alcohol	human xenobiotic metabolite
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.	2.02	1	0	branched-chain saturated fatty acid; methyl-branched fatty acid; short-chain fatty acid
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.	2.44	2	0	fluoroalkanoic acid	human xenobiotic metabolite; NMR chemical shift reference compound; reagent
bromthymol blue Bromthymol Blue: A pH sensitive dye that has been used as an indicator in many laboratory reactions.. bromothymol blue : A member of the class of 2,1-benzoxathioles that is 2,1-benzoxathiole 1,1-dioxide in which both of the hydrogens at position 3 have been substituted by 3-bromo-4-hydroxy-5-isopropyl-2-methylphenyl groups.	1.97	1	0	2,1-benzoxathiole; arenesulfonate ester; organobromine compound; polyphenol; sultone	acid-base indicator; dye; two-colour indicator
quinic acid (-)-quinic acid : The (-)-enantiomer of quinic acid.	2.01	1	0
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.	7.37	2	0	alkadiene; hemiterpene; volatile organic compound	plant metabolite
chloroacetone [no description available]	1.96	1	0	alpha-chloroketone
acrylic acid acrylic acid: RN given refers to parent cpd. acrylic acid : A alpha,beta-unsaturated monocarboxylic acid that is ethene substituted by a carboxy group.	2.44	2	0	alpha,beta-unsaturated monocarboxylic acid	metabolite
rhodamine b rhodamine B: RN & N1 from 9th CI Form Index; RN given refers to parent cpd; structure in Merck Index, 9th ed, #7973; TETRAETHYLRHODAMINE was see RHODAMINES 1975-93; use RHODAMINES to search TETRAETHYLRHODAMINE 1975-93. rhodamine B : An organic chloride salt having N-[9-(2-carboxyphenyl)-6-(diethylamino)-3H-xanthen-3-ylidene]-N-ethylethanaminium as the counterion. An amphoteric dye commonly used as a fluorochrome.	2.1	1	0	organic chloride salt; xanthene dye	fluorescent probe; fluorochrome; histological dye
methylprednisolone Methylprednisolone: A PREDNISOLONE derivative with similar anti-inflammatory action.. 6alpha-methylprednisolone : The 6alpha-stereoisomer of 6-methylprednisolone.	1.93	1	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.	5.54	22	0	organic heteropentacyclic compound; rotenones	antineoplastic agent; metabolite; mitochondrial NADH:ubiquinone reductase inhibitor; phytogenic insecticide; piscicide; toxin
9,10-anthraquinone 9,10-anthraquinone : An anthraquinone that is anthracene in which positions 9 and 10 have been oxidised to carbonyls.	2.11	1	0	anthraquinone
1-hydroxy-2-naphthoic acid 1-hydroxy-2-naphthoic acid: RN given refers to parent cpd. 1-hydroxy-2-naphthoic acid : A naphthoic acid with the carboxy group at position 2 and carrying a hydroxy substituent at the 1-position. It is a xenobiotic metabolite produced by the biodegradation of phenanthrene by microorganisms.	2.07	1	0	hydroxy monocarboxylic acid; naphthoic acid; naphthols	bacterial xenobiotic metabolite; fungal xenobiotic metabolite
2,4,6-trichlorophenol [no description available]	7.04	1	0	trichlorophenol	carcinogenic agent
thiophene-3-carboxylic acid thiophene-3-carboxylic acid: structure in first source	2.08	1	0
5-methylsalicylic acid [no description available]	2.15	1	0
quinoxalines quinoxaline : A naphthyridine in which the nitrogens are at positions 1 and 4.	1.98	1	0	mancude organic heterobicyclic parent; naphthyridine; ortho-fused heteroarene
1,2,3,4-tetrahydroisoquinoline 1,2,3,4-tetrahydroisoquinoline: RN given refers to cpd with locants as specified	2.02	1	0	isoquinolines
quinoline [no description available]	1.92	1	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinolines
veratryl alcohol (3,4-dimethoxyphenyl)methanol : A member of the class of benzyl alcohols that is benzyl alcohol in which the hydrogens at positions 3 and 4 of the phenyl group are substituted by methoxy groups.	2.38	2	0	benzyl alcohols; dimethoxybenzene; primary alcohol	fungal 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)	2.11	1	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.	2.05	1	0	indene; ortho-fused bicyclic arene
5-nitrosalicylic acid 5-nitrosalicylic acid : A monohydroxybenzoic acid in which the hydroxy group is ortho- to the carboxylic acid group and which has a nitro substituent para- to the phenolic hydroxy group.	2.15	1	0	4-nitrophenols; monohydroxybenzoic acid
sulfosalicylic acid 5-sulfosalicylic acid : An arenesulfonic acid that is benzoic acid substituted by a hydroxy at position C-2 and a sulfo group at C-5.	2.1	1	0	arenesulfonic acid; benzoic acids; phenols	metabolite
nitrobenzene nitrobenzene : A nitroarene consisting of benzene carrying a single nitro substituent. An industrial chemical used widely in the production of aniline.	2.05	1	0	nitroarene; nitrobenzenes
3-aminobenzoic acid 3-aminobenzoic acid: RN given refers to parent cpd. 3-aminobenzoic acid : An aminobenzoic acid carrying an amino group at position 3.	2.11	1	0	aminobenzoic acid
adrenalone adrenalone: RN given refers to parent cpd	2.08	1	0	aromatic ketone
4-bromophenacyl bromide 4-bromophenacyl bromide: phospholipidase A(2) inhibitor; structure	2	1	0
boric acid [no description available]	2.44	2	0	boric acids	astringent
diethyl malonate diethyl malonate: isomer of diethylmalonic acid; one of most used compounds in drug synthesis, don't confuse with ethylmalonic acid	2.69	3	0	dicarboxylic acid
acrolein [no description available]	2.37	2	0	enal	herbicide; human xenobiotic metabolite; toxin
3-chloropropionic acid 3-chloropropionic acid: structure	2.01	1	0
methyl malonate methyl malonate: do not confuse with methylmalonate, i.e., malonic acid substituted with a methyl group on C2; structure	2.67	3	0
melamine melamine: RN given refers to parent cpd; structure. melamine : A trimer of cyanamide, with a 1,3,5-triazine skeleton.	2.15	1	0	triamino-1,3,5-triazine	xenobiotic metabolite
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
3-hydroxypyridine 3-hydroxypyridine: RN given refeirs to parent cpd. 3-pyridinol : A monohydroxypyridine that is pyridine in which the hydrogen at position 3 has been replaced by a hydroxy group. It has been detected as a thermal degradation product from the smoke of the burning leaves of Salvia divinorum, a Mexican psychoactive plant.	2.05	1	0	monohydroxypyridine
dicyanmethane malononitrile : A dinitrile that is methane substituted by two cyano groups.	2.34	2	0	aliphatic nitrile; dinitrile
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.	3.14	5	0	pyrrole; secondary amine
thiophenes Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.	2.11	1	0	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
succinamide [no description available]	2.05	1	0
piperidine [no description available]	2.05	1	0	azacycloalkane; piperidines; saturated organic heteromonocyclic parent; secondary amine	base; catalyst; human metabolite; non-polar solvent; plant metabolite; protic solvent; reagent
veratraldehyde [no description available]	2	1	0	benzaldehydes; dimethoxybenzene	antifungal agent
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.	2.11	1	0	imidazolidinone; ureas
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.	2.08	1	0	anthrapyrazole; aromatic ketone; cyclic ketone	antineoplastic agent; c-Jun N-terminal kinase inhibitor; geroprotector
1-naphthylamine 1-Naphthylamine: A suspected industrial carcinogen (and listed as such by OSHA). Its N-hydroxy metabolite is strongly carcinogenic and mutagenic.. naphthylamine : A primary arylamine that is naphthalene substituted by an amino group at unspecified position.. 1-naphthylamine : A naphthylamine that is naphthalene substituted by an amino group at position 1.	2.03	1	0	naphthylamine	human xenobiotic metabolite
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.	2.72	3	0	alpha,beta-unsaturated monocarboxylic acid; cyclohexenecarboxylic acid; hydroxy monocarboxylic acid	Escherichia coli metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
hexanoic acid hexanoic acid : A C6, straight-chain saturated fatty acid.	2.02	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	human metabolite; plant metabolite
n-lauroylethanolamine lauroylethanolamide: N-acylethanolamine. N-(dodecanoyl)ethanolamine : An N-(long-chain-acyl)ethanolamine resulting from the formal condensation of the carboxy group of dodecanoic acid (myristic acid) with the amino group of ethanolamine.	2.13	1	0	N-(long-chain-acyl)ethanolamine; N-(saturated fatty acyl)ethanolamine
sodium cyanide Sodium Cyanide: A highly poisonous compound that is an inhibitor of many metabolic processes and is used as a test reagent for the function of chemoreceptors. It is also used in many industrial processes.. sodium cyanide : A cyanide salt containing equal numbers of sodium cations and cyanide anions.	2.02	1	0	cyanide salt; one-carbon compound; sodium salt	EC 1.15.1.1 (superoxide dismutase) inhibitor
3-o-methylglucose 3-O-Methylglucose: A non-metabolizable glucose analogue that is not phosphorylated by hexokinase. 3-O-Methylglucose is used as a marker to assess glucose transport by evaluating its uptake within various cells and organ systems. (J Neurochem 1993;60(4):1498-504). 3-O-methyl-D-glucose : A D-aldohexose that is D-glucose in which the hydrogen of the hydroxy group at position 3 has been substituted by a methyl group. It is a non-metabolisable glucose analogue that is not phosphorylated by hexokinase and is used as a marker to assess glucose transport by evaluating its uptake within various cells and organ systems.	1.96	1	0	D-aldohexose derivative
potassium cyanide [no description available]	3.49	8	0	cyanide salt; one-carbon compound; potassium salt	EC 1.15.1.1 (superoxide dismutase) inhibitor; EC 1.9.3.1 (cytochrome c oxidase) inhibitor; neurotoxin
quinazolines Quinazolines: A group of aromatic heterocyclic compounds that contain a bicyclic structure with two fused six-membered aromatic rings, a benzene ring and a pyrimidine ring.. quinazoline : A mancude organic heterobicyclic parent that is naphthalene in which the carbon atoms at positions 1 and 3 have been replaced by nitrogen atoms.. quinazolines : Any organic heterobicyclic compound based on a quinazoline skeleton and its substituted derivatives.	2.08	1	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.	2.37	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.	2.69	3	0	indazole
adamantane Adamantane: A tricyclo bridged hydrocarbon.	2.46	2	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.	2.13	1	0	isoxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
oxazoles Oxazoles: Five-membered heterocyclic ring structures containing an oxygen in the 1-position and a nitrogen in the 3-position, in distinction from ISOXAZOLES where they are at the 1,2 positions.. 1,3-oxazole : A five-membered monocyclic heteroarene that is an analogue of cyclopentadiene with O in place of CH2 at position 1 and N in place of CH at position 3.. oxazole : An azole based on a five-membered heterocyclic aromatic skeleton containing one N and one O atom.	2.75	3	0	1,3-oxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
thiazoles [no description available]	3.09	5	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.	7.36	2	0	diazine; pyrimidines	Daphnia magna metabolite
methylphenazonium methosulfate Methylphenazonium Methosulfate: Used as an electron carrier in place of the flavine enzyme of Warburg in the hexosemonophosphate system and also in the preparation of SUCCINIC DEHYDROGENASE.	1.98	1	0	azaheterocycle sulfate salt; phenazines
hydrazine diamine : Any polyamine that contains two amino groups.	7.48	2	0	azane; hydrazines	EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
gamma-resorcylic acid [no description available]	2.15	1	0	dihydroxybenzoic acid	metabolite
2h-benzo(a)quinolizin-2-ol, 2-ethyl-1,3,4,6,7,11b-hexahydro-3-isobutyl-9,10-dimethoxy- 2H-Benzo(a)quinolizin-2-ol, 2-Ethyl-1,3,4,6,7,11b-hexahydro-3-isobutyl-9,10-dimethoxy-: Proposed catecholamine depletor.	2	1	0
5-chlorosalicylic acid 5-chlorosalicylic acid: major metabolite of meseclazone; RN given refers to parent cpd. 5-chlorosalicylic acid : A monohydroxybenzoic acid that is 2-hydroxybenzoic acid (salicylic acid) in which the hydrogen at position 5 is replaced by chlorine.	2.11	1	0	chlorobenzoic acid; monochlorobenzenes; monohydroxybenzoic acid
citrulline citrulline : The parent compound of the citrulline class consisting of ornithine having a carbamoyl group at the N(5)-position.	2.92	4	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
cyanamide Cyanamide: A cyanide compound which has been used as a fertilizer, defoliant and in many manufacturing processes. It often occurs as the calcium salt, sometimes also referred to as cyanamide. The citrated calcium salt is used in the treatment of alcoholism.. cyanamide : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by an amino group.	1.96	1	0	nitrile; one-carbon compound	EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor
cyanogen cyanogen: structure. oxalonitrile : A dinitrile that is ethane substituted by two cyano groups.	6.93	1	0	dinitrile; pseudohalogen
3-aminopyridine [no description available]	2.11	1	0
ketene ketene: structure. ketene : Carbonyl compounds where the C=O bond is conjugated to an alkylidene group.	2.06	1	0	ketene
mesoxalic acid mesoxalic acid: structure	1.96	1	0	oxo dicarboxylic acid
funiculosin (anthraquinone) funiculosin (anthraquinone): see also a pyridone cpd called funiculosin; structure	1.96	1	0	trihydroxyanthraquinone
rhein [no description available]	3.11	1	0	dihydroxyanthraquinone
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.	3.11	5	0	dicarboxylic acid; L-proline derivative; non-proteinogenic L-alpha-amino acid; pyrrolidinecarboxylic acid	antinematodal drug; excitatory amino acid agonist
benzohydroxamic acid [no description available]	7	1	0
3,5-pyridinedicarboxylic acid 3,5-pyridinedicarboxylic acid: structure in first source	2.11	1	0	pyridinedicarboxylic acid
dipicolinic acid dipicolinic acid : A pyridinedicarboxylic acid carrying two carboxy groups at positions 2 and 6.	1.93	1	0	pyridinedicarboxylic acid	bacterial metabolite
isovaleric acid isovaleric acid: structure. isovaleric acid : A C5, branched-chain saturated fatty acid.	3.11	1	0	branched-chain saturated fatty acid; methylbutyric acid; short-chain fatty acid	mammalian metabolite; plant metabolite
cyanogen bromide Cyanogen Bromide: Cyanogen bromide (CNBr). A compound used in molecular biology to digest some proteins and as a coupling reagent for phosphoroamidate or pyrophosphate internucleotide bonds in DNA duplexes.	2.33	2	0
phenylacetylene phenylacetylene: can polymerize into DENDRIMERS	2.04	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.	2.4	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.	6.96	1	0	carbodiimide	ATP synthase inhibitor; cross-linking reagent; peptide coupling reagent
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.	2.02	1	0	alkane; volatile organic compound	fuel additive; nephrotoxin; non-polar solvent
malondialdehyde Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.	2.88	4	0	dialdehyde	biomarker
aceturic acid aceturic acid: structure. N-acetylglycine : An N-acylglycine where the acyl group is specified as acetyl.	2.04	1	0	N-acetyl-amino acid; N-acylglycine	human metabolite
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.	2.38	2	0	arenesulfonic acid; arylmercury compound
3-nitrophenol [no description available]	2.05	1	0	3-nitrophenols
silver acetate silver acetate: RN refers to acetic acid, silver (1+) salt	2.05	1	0
benzene 1,2,3-tricarboxylic acid benzene 1,2,3-tricarboxylic acid: structure given in first source; inhibits phosphoenolpyruvate carboxykinase	1.97	1	0
docusate Dioctyl Sulfosuccinic Acid: All-purpose surfactant, wetting agent, and solubilizer used in the drug, cosmetics, and food industries. It has also been used in laxatives and as cerumenolytics. It is usually administered as either the calcium, potassium, or sodium salt.	2.04	1	0	diester; organosulfonic acid
phenarsazine chloride phenarsazine chloride: extremely irritating & poisonous; used as a war gas; structure	2.02	1	0
3-bromopropionic acid [no description available]	2.01	1	0
2,2-dimethylmalonate dimethylmalonic acid : A dicarboxylic acid that is malonic acid in which both methylene hydrogens have been replaced by methyl groups.	2.11	1	0	dicarboxylic acid	fatty acid synthesis inhibitor
ethylmalonic acid ethylmalonic acid: don't confuse with diethyl malonate, which is a diester. ethylmalonate : A dicarboxylic acid anion obtained by deprotonation of at least one of the carboxy groups of ethylmalonic acid.. ethylmalonic acid : A dicarboxylic acid obtained by substitution of one of the methylene hydrogens of malonic acid by an ethyl group.	2.15	1	0	dicarboxylic acid; dicarboxylic fatty acid	human metabolite
phenylglyoxylic acid phenylglyoxylic acid: styrene metabolite. phenylglyoxylic acid : A 2-oxo monocarboxylic acid that is glyoxylic acid in which the aldehyde hydrogen is substituted by a phenyl group.	3.1	1	0	2-oxo monocarboxylic acid	biomarker; human xenobiotic metabolite
2-hydroxyphenylacetic acid 2-hydroxyphenylacetic acid: structure. (2-hydroxyphenyl)acetic acid : A hydroxy monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 2-hydroxyphenyl group. It is a metabolite of phenylalanine and is excreted in the urine of patients suffering from diseases like phenylketonuria.	2.15	1	0	hydroxy monocarboxylic acid; phenols	human metabolite; mouse metabolite
3-hydroxybenzeneacetic acid 3-hydroxybenzeneacetic acid: metabolite of L-dopa; structure. 3-hydroxyphenylacetic acid : A monocarboxylic acid that is phenylacetic acid in which the hydrogen at position 3 on the benzene ring is replaced by a hydroxy group.	2.08	1	0	monocarboxylic acid; phenols	human xenobiotic metabolite
erythromycin Erythromycin: A bacteriostatic antibiotic macrolide produced by Streptomyces erythreus. Erythromycin A is considered its major active component. In sensitive organisms, it inhibits protein synthesis by binding to 50S ribosomal subunits. This binding process inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins.. erythromycin : Any of several wide-spectrum macrolide antibiotics obtained from actinomycete Saccharopolyspora erythraea (formerly known as Streptomyces erythraeus).. erythromycin A : An erythromycin that consists of erythronolide A having 2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl and 3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl residues attahced at positions 4 and 6 respectively.	2.92	4	0	cyclic ketone; erythromycin
phenylphosphate phenylphosphate: structure given in first source. phenyl phosphate : An aryl phosphate resulting from the mono-esterification of phosphoric acid with phenol.	2.01	1	0	aryl phosphate	mouse metabolite
1,2-cyclohexanedione cyclohexanedione : Cyclohexanones carrying two oxo substituents.. cyclohexane-1,2-dione : A cyclohexanedione carrying oxo substituents at positions 1 and 2.	2.1	1	0	cyclohexanedione
3-hydroxypicolinic acid [no description available]	2.11	1	0	monocarboxylic acid; monohydroxypyridine	MALDI matrix material
3-hydroxy-1-benzopyran-2-one 3-hydroxycoumarin: Photoprotective from sea urchin gametes and embryonic cells; structure in first source. hydroxycoumarin : Any coumarin carrying at least one hydroxy substituent.	2.08	1	0	hydroxycoumarin
fonofos Fonofos: An organothiophosphorus cholinesterase inhibitor that is used as an insecticide.	2.01	1	0	organic thiophosphate; organothiophosphate insecticide	agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor
2-acetylpyridine 2-acetylpyridine: structure in first source	7.06	1	0	aromatic ketone
sodium hydroxide Sodium Hydroxide: A highly caustic substance that is used to neutralize acids and make sodium salts. (From Merck Index, 11th ed)	2.03	1	0	alkali metal hydroxide
manganese dioxide [no description available]	7.25	1	0	manganese molecular entity; metal oxide
tricarballylic acid tricarballylic acid: RN given refers to parent cpd. tricarballylic acid : A tricarboxylic acid that is glutaric acid in which one of the beta-hydrogens is substituted by a carboxy group.	2.11	1	0	tricarboxylic acid
d-alpha tocopherol Vitamin E: A generic descriptor for all TOCOPHEROLS and TOCOTRIENOLS that exhibit ALPHA-TOCOPHEROL activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of ISOPRENOIDS.. tocopherol : A collective name for a group of closely related lipids that contain a chroman-6-ol nucleus substituted at position 2 by a methyl group and by a saturated hydrocarbon chain consisting of three isoprenoid units. They are designated as alpha-, beta-, gamma-, and delta-tocopherol depending on the number and position of additional methyl substituents on the aromatic ring. Tocopherols occur in vegetable oils and vegetable oil products, almost exclusively with R,R,R configuration. Tocotrienols differ from tocopherols only in having three double bonds in the hydrocarbon chain.. vitamin E : Any member of a group of fat-soluble chromanols that exhibit biological activity against vitamin E deficiency. The vitamers in this class consists of a chroman-6-ol core which is substituted at position 2 by a methyl group and (also at position 2) either a saturated or a triply-unsaturated hydrocarbon chain consisting of three isoprenoid units. The major function of vitamin E is to act as a natural antioxidant by scavenging free radicals and molecular oxygen.. (R,R,R)-alpha-tocopherol : An alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils.	2.37	2	0	alpha-tocopherol	algal metabolite; antiatherogenic agent; anticoagulant; antioxidant; antiviral agent; EC 2.7.11.13 (protein kinase C) inhibitor; immunomodulator; micronutrient; nutraceutical; plant metabolite
ethyldimethylaminopropyl carbodiimide Ethyldimethylaminopropyl Carbodiimide: Carbodiimide cross-linking reagent.	2.05	1	0
pristane pristane: structure. pristane : A norterpene that is an acyclic saturated hydrocarbon derived from phytane by loss of its C-16 terminal methyl group.	2.31	1	0	long-chain alkane; norterpene	biomarker; immunological adjuvant
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.	2.44	2	0	benzochromene; diterpenoid; phytocannabinoid; polyketide	cannabinoid receptor agonist; epitope; hallucinogen; metabolite; non-narcotic analgesic
amiloride Amiloride: A pyrazine compound inhibiting SODIUM reabsorption through SODIUM CHANNELS in renal EPITHELIAL CELLS. This inhibition creates a negative potential in the luminal membranes of principal cells, located in the distal convoluted tubule and collecting duct. Negative potential reduces secretion of potassium and hydrogen ions. Amiloride is used in conjunction with DIURETICS to spare POTASSIUM loss. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p705). amiloride : A member of the class of pyrazines resulting from the formal monoacylation of guanidine with the carboxy group of 3,5-diamino-6-chloropyrazine-2-carboxylic acid.	1.98	1	0	aromatic amine; guanidines; organochlorine compound; pyrazines	diuretic; sodium channel blocker
betamethasone valerate Betamethasone Valerate: The 17-valerate derivative of BETAMETHASONE. It has substantial topical anti-inflammatory activity and relatively low systemic anti-inflammatory activity.. betamethasone valerate : A steroid ester that is betamethasone in which the hydroxy group at the 17alpha position has been converted to the corresponding pentanoate ester.	2.25	1	0	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; fluorinated steroid; primary alpha-hydroxy ketone; steroid ester	anti-inflammatory drug
n-isopropylacrylamide N-isopropylacrylamide: can polymerize with glycidyl acrylate to form reactive water-soluble polymer that can react with the amino groups of enzymes-proteins or other ligands	3.55	2	0
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.	2.39	2	0	2-benzofurans; gamma-lactone; organic heteropentacyclic compound; oxaspiro compound; polyphenol; xanthene dye	fluorescent dye; radioopaque medium
oxiniacic acid [no description available]	2.08	1	0	aromatic carboxylic acid; pyridines
6-aminonicotinic acid 6-aminonicotinic acid: RN given refers to parent cpd. 6-aminonicotinic acid : An aminonicotinic acid in which the amino group is situated at position 6 of the pyridine ring.	2.11	1	0	aminonicotinic acid; aminopyridine; aromatic amine	metabolite
mannose mannopyranose : The pyranose form of mannose.	1.94	1	0	D-aldohexose; D-mannose; mannopyranose	metabolite
iproclozide iproclozide: structure	1.97	1	0	aromatic ether
streptomycin [no description available]	2.44	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.	1.92	1	0	carbon oxoanion
2,4,5-trimethoxybenzaldehyde asaronaldehyde: from Piper clusii (Piperaceae); structure in first source	2.01	1	0	carbonyl compound
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.	2.41	2	0	diastereoisomeric mixture; homocysteines; non-proteinogenic alpha-amino acid; sulfoximide	EC 6.3.2.2 (glutamate--cysteine ligase) inhibitor; ferroptosis inducer
carboxin Carboxin: A systemic agricultural fungicide and seed treatment agent.. carboxin : An anilide obtained by formal condensation of the amino group of aniline with the carboxy group of 2-methyl-5,6-dihydro-1,4-oxathiine-3-carboxylic acid. A fungicide for control of bunts and smuts that is normally used as a seed treatment.	3.11	1	0	anilide fungicide; anilide; enamide; organosulfur heterocyclic compound; oxacycle; secondary carboxamide	antifungal agrochemical; EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor
2-aminobenzyl alcohol 2-aminobenzyl alcohol: structure given in first source	2.15	1	0
maleic hydrazide Maleic Hydrazide: 1,2-Dihydro-3,6-pyridazinedione. A herbicide and plant growth regulator; also used to control suckering of tobacco. Its residue in food and tobacco is highly toxic, causing CNS disturbances and liver damage.	7	1	0	pyridazinone
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.	3.7	10	0	amino dicarboxylic acid; D-alpha-amino acid; D-aspartic acid derivative; secondary amino compound	neurotransmitter 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.	1.96	1	0	cyclic ketone; gamma-lactone; organic heterotricyclic compound; secondary alcohol; sesquiterpene lactone	anti-inflammatory agent; antineoplastic agent; metabolite; plant metabolite
lanthanum [no description available]	2.05	1	0	f-block element atom; lanthanoid atom; scandium group element atom
manganese Manganese: A trace element with atomic symbol Mn, atomic number 25, and atomic weight 54.94. It is concentrated in cell mitochondria, mostly in the pituitary gland, liver, pancreas, kidney, and bone, influences the synthesis of mucopolysaccharides, stimulates hepatic synthesis of cholesterol and fatty acids, and is a cofactor in many enzymes, including arginase and alkaline phosphatase in the liver. (From AMA Drug Evaluations Annual 1992, p2035). manganese(4+) : A manganese cation that is monoatomic and has a formal charge of +4.	3.61	9	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.	7.36	2	0	elemental mercury; zinc group element atom	neurotoxin
molybdenum Molybdenum: A metallic element with the atomic symbol Mo, atomic number 42, and atomic weight 95.95. It is an essential trace element, being a component of the enzymes xanthine oxidase, aldehyde oxidase, and nitrate reductase.	2.7	3	0	chromium group element atom	micronutrient
osmium Osmium: A very hard, gray, toxic, and nearly infusible metal element, atomic number 76, atomic weight 190.2, symbol Os.	2.06	1	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.	2.74	3	0	metal allergen; nickel group element atom; platinum group metal atom
platinum Platinum: A heavy, soft, whitish metal, resembling tin, with atomic number 78, atomic weight 195.084, symbol Pt. It is used in manufacturing equipment for laboratory and industrial use. It occurs as a black powder (platinum black) and as a spongy substance (spongy platinum) and may have been known in Pliny's time as alutiae.	7.75	3	0	elemental platinum; nickel group element atom; platinum group metal 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.	2.11	1	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.	3.14	5	0	iron group element atom; platinum group metal atom
silver Silver: An element with the atomic symbol Ag, atomic number 47, and atomic weight 107.87. It is a soft metal that is used medically in surgical instruments, dental prostheses, and alloys. Long-continued use of silver salts can lead to a form of poisoning known as ARGYRIA.	2.57	2	0	copper group element atom; elemental silver	Escherichia coli metabolite
terbium Terbium: An element of the rare earth family of metals. It has the atomic symbol Tb, atomic number 65, and atomic weight 158.92.	1.99	1	0	f-block element atom; lanthanoid 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.	2.03	1	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.	2.37	2	0	titanium group element atom
cadmium Cadmium: An element with atomic symbol Cd, atomic number 48, and atomic weight 112.41. It is a metal and ingestion will lead to CADMIUM POISONING.. elemental cadmium : An element in the zinc group of the periodic table with atomic number 48, atomic mass 112, M.P. 321degreeC, and B.P. 765degreeC). An odourless, tasteless, and highly poisonous soft, ductile, lustrous metal with electropositive properties. It has eight stable isotopes: (106)Cd, (108)Cd,(110)Cd, (111)Cd, (112)Cd, (113)Cd, (114)Cd and (116)Cd, with (112)Cd and (114)Cd being the most common.	2.93	4	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.	3.15	5	0	f-block element atom; lanthanoid atom
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.	2.42	2	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.	1.99	1	0	f-block element atom; lanthanoid atom
zirconium Zirconium: A rather rare metallic element with atomic number 40, atomic weight 91.224, and symbol Zr.	2.05	1	0	titanium group element atom
mercuric chloride Mercuric Chloride: Mercury chloride (HgCl2). A highly toxic compound that volatizes slightly at ordinary temperature and appreciably at 100 degrees C. It is corrosive to mucous membranes and used as a topical antiseptic and disinfectant.. mercury dichloride : A mercury coordination entity made up of linear triatomic molecules in which a mercury atom is bonded to two chlorines. Water-soluble, it is highly toxic. Once used in a wide variety of applications, including preserving wood and anatomical specimens, embalming and disinfecting, as an intensifier in photography, as a mordant for rabbit and beaver furs, and freeing gold from lead, its use has markedly declined as less toxic alternatives have been developed.	2.36	2	0	mercury coordination entity	sensitiser
sodium nitrate sodium nitrate : The inorganic nitrate salt of sodium.	2.02	1	0	inorganic nitrate salt; inorganic sodium salt	fertilizer; NMR chemical shift reference compound
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.	2.07	1	0	mononuclear parent hydride; phosphanes; phosphine	carcinogenic agent; fumigant insecticide
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.	2.01	1	0	diatomic bromine
bromic acid [no description available]	2.15	1	0	bromine oxoacid
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.	1.98	1	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.	2.11	1	0	inorganic nitrate salt; silver salt	astringent
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	2.93	4	0	dihydrogen
fluorine Fluorine: A nonmetallic, diatomic gas that is a trace element and member of the halogen family. It is used in dentistry as fluoride (FLUORIDES) to prevent dental caries.	2.1	1	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.	2.4	2	0	diatomic chlorine; gas molecular entity	bleaching agent
cupric bromide [no description available]	2.05	1	0
molybdate ion molybdate : A divalent inorganic anion obtained by removal of both protons from molybdic acid	1.99	1	0	divalent inorganic anion; molybdenum oxoanion	Escherichia coli metabolite
galactose aldohexose : A hexose with a (potential) aldehyde group at one end.	1.96	1	0
thallium sulfate thallium sulfate: RN given refers to unspecified Tl salt. thallium sulfate : A metal sulfate in which the counterion is thallium and the ratio of thallium to sulfate is 2:1. It is a rodenticide used to control rats, squirrels, mice, moles, prairie dogs, ants and cockroaches. It is no longer registered for pesticide use in the United States.	1.97	1	0	metal sulfate; thallium molecular entity	insecticide; rodenticide
chlorine dioxide chlorine dioxide: equal or superior to chlorine when used as wastewater disinfectant	3.74	10	0	chlorine dioxide
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.	2.04	1	0	cadmium coordination entity
calcium nitrate calcium nitrate: an amylopsin activator. calcium nitrate : Inorganic nitrate salt of calcium.	7.31	1	0	calcium salt; inorganic nitrate salt	fertilizer
barium chloride barium chloride: RN given refers to parent cpd. barium chloride : The inorganic dichloride salt of barium.	1.97	1	0	barium salt; inorganic chloride	potassium channel blocker
chrysotile Asbestos, Serpentine: A type of asbestos that occurs in nature as the dihydrate of magnesium silicate. It exists in two forms: antigorite, a plated variety, and chrysotile, a fibrous variety. The latter makes up 95% of all asbestos products. (From Merck Index, 11th ed, p.893)	2.17	1	0
ammonium chloride Ammonium Chloride: An acidifying agent that has expectorant and diuretic effects. Also used in etching and batteries and as a flux in electroplating.. ammonium chloride : An inorganic chloride having ammonium as the counterion.	1.96	1	0	ammonium salt; inorganic chloride	ferroptosis inhibitor
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.	2.11	1	0	titanium oxides	food colouring
3,5-dichlorocatechol 3,5-dichlorocatechol : A dichlorocatechol carrying chloro groups at positions 3 and 5.	2.03	1	0	dichlorocatechol
tiletamine hydrochloride Cyclohexanones: Cyclohexane ring substituted by one or more ketones in any position.. cyclohexanones : Any alicyclic ketone based on a cyclohexane skeleton and its substituted derivatives thereof.	2.46	2	0
selegiline Selegiline: A selective, irreversible inhibitor of Type B monoamine oxidase that is used for the treatment of newly diagnosed patients with PARKINSON DISEASE, and for the treatment of depressive disorders. The compound without isomeric designation is Deprenyl.	2.4	2	0	selegiline; terminal acetylenic compound	geroprotector
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.	2.39	2	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
fluorides [no description available]	2.37	2	0	halide anion; monoatomic fluorine
iodine [no description available]	2.76	3	0	halide anion; monoatomic iodine	human 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.	2.43	2	0	L-tyrosine derivative; non-proteinogenic L-alpha-amino acid; O(4)-phosphotyrosine	Escherichia coli metabolite; immunogen
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	4.49	24	0	benzenes; phenyl acetates
diethyl succinate diethyl succinate: carboxylesterase substrate	1.96	1	0	fatty acid ester
pyrrolidine [no description available]	2.78	3	0	azacycloalkane; pyrrolidines; saturated organic heteromonocyclic parent
1,4-dioxane 1,4-dioxane: dehydrating agent; polar solvent miscible both with water & most organic solvents. dioxane : Any member of the class of dioxanes that is a cyclohexane in which two carbon atoms are replaced by oxygen atoms.. 1,4-dioxane : A dioxane with oxygen atoms at positions 1 and 4.	2.03	1	0	dioxane; volatile organic compound	carcinogenic agent; metabolite; NMR chemical shift reference compound; non-polar solvent
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.	2.41	1	0	ortho- and peri-fused polycyclic arene	fluorescent probe; persistent organic pollutant
transferrin Transferrin: An iron-binding beta1-globulin that is synthesized in the LIVER and secreted into the blood. It plays a central role in the transport of IRON throughout the circulation. A variety of transferrin isoforms exist in humans, including some that are considered markers for specific disease states.	1.98	1	0
alkenes [no description available]	3.43	7	0
calcium oxalate Calcium Oxalate: The calcium salt of oxalic acid, occurring in the urine as crystals and in certain calculi.. calcium oxalate : The calcium salt of oxalic acid, which in excess in the urine may lead to formation of oxalate calculi (kidney stones).	1.97	1	0	organic calcium salt
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.	4.54	25	0	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
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).	2.7	3	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.	2.94	4	0	pseudohalide anion	mitochondrial respiratory-chain inhibitor
5-hydroxynicotinic acid [no description available]	2.11	1	0	aromatic carboxylic acid; pyridines
nigericin Nigericin: A polyether antibiotic which affects ion transport and ATPase activity in mitochondria. It is produced by Streptomyces hygroscopicus. (From Merck Index, 11th ed). nigericin : A polyether antibiotic which affects ion transport and ATPase activity in mitochondria. It is produced by Streptomyces hygroscopicus.	2.39	2	0	polycyclic ether	antibacterial agent; antimicrobial agent; bacterial metabolite; potassium ionophore
dimethyl suberimidate Dimethyl Suberimidate: The methyl imidoester of suberic acid used to produce cross links in proteins. Each end of the imidoester will react with an amino group in the protein molecule to form an amidine.	1.97	1	0
s-adenosylmethionine acylcarnitine: structure in first source. S-adenosyl-L-methioninate : A sulfonium betaine that is a conjugate base of S-adenosyl-L-methionine obtained by the deprotonation of the carboxy group.	2.31	1	0	sulfonium betaine	human metabolite
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.	2.02	1	0	azide; pyrimidine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; HIV-1 reverse transcriptase inhibitor
substance p [no description available]	1.98	1	0	peptide	neurokinin-1 receptor agonist; neurotransmitter; vasodilator agent
fluorescamine Fluorescamine: A nonfluorescent reagent for the detection of primary amines, peptides and proteins. The reaction products are highly fluorescent.	1.98	1	0
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.	2.39	2	0	5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate	antihypertensive agent; calcium channel blocker; vasodilator agent
1-methyl-4-phenylpyridinium 1-Methyl-4-phenylpyridinium: An active neurotoxic metabolite of 1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE. The compound reduces dopamine levels, inhibits the biosynthesis of catecholamines, depletes cardiac norepinephrine and inactivates tyrosine hydroxylase. These and other toxic effects lead to cessation of oxidative phosphorylation, ATP depletion, and cell death. The compound, which is related to PARAQUAT, has also been used as an herbicide.. N-methyl-4-phenylpyridinium : A pyridinium ion that is N-methylpyridinium having a phenyl substituent at the 4-position.	2.39	2	0	pyridinium ion	apoptosis inducer; herbicide; human xenobiotic metabolite; neurotoxin
ng-nitroarginine methyl ester NG-Nitroarginine Methyl Ester: A non-selective inhibitor of nitric oxide synthase. It has been used experimentally to induce hypertension.	2.41	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.	2.21	1	0	cyclic ketone; enone; primary alcohol; secondary alpha-hydroxy ketone; trichothecene; triol	mycotoxin
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid [no description available]	2.41	2	0	chromanol; monocarboxylic acid; phenols	antioxidant; ferroptosis inhibitor; neuroprotective agent; radical scavenger; Wnt signalling inhibitor
1-carboxyglutamic acid 1-Carboxyglutamic Acid: Found in various tissues, particularly in four blood-clotting proteins including prothrombin, in kidney protein, in bone protein, and in the protein present in various ectopic calcifications.	1.97	1	0
kathon cg Kathon 886: industrial biocide & cosmetic preservative formulation; contains methylcholoro-isothiazolinone and methylcholoroisothiazolinone	1.97	1	0
paroxetine Paroxetine: A serotonin uptake inhibitor that is effective in the treatment of depression.. paroxetine : A benzodioxole that consists of piperidine bearing 1,3-benzodioxol-5-yloxy)methyl and 4-fluorophenyl substituents at positions 3 and 4 respectively; the (3S,4R)-diastereomer. Highly potent and selective 5-HT uptake inhibitor that binds with high affinity to the serotonin transporter (Ki = 0.05 nM). Ki values are 1.1, 350 and 1100 nM for inhibition of [3H]-5-HT, [3H]-l-NA and [3H]-DA uptake respectively. Displays minimal affinity for alpha1-, alpha2- or beta-adrenoceptors, 5-HT2A, 5-HT1A, D2 or H1 receptors at concentrations below 1000 nM, however displays weak affinity for muscarinic ACh receptors (Ki = 42 nM). Antidepressant and anxiolytic in vivo.	2.04	1	0	aromatic ether; benzodioxoles; organofluorine compound; piperidines	antidepressant; anxiolytic drug; hepatotoxic agent; P450 inhibitor; serotonin uptake inhibitor
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.	1.98	1	0	indolizidine alkaloid	antineoplastic agent; EC 3.2.1.114 (mannosyl-oligosaccharide 1,3-1,6-alpha-mannosidase) inhibitor; immunological adjuvant; plant metabolite
simvastatin Simvastatin: A derivative of LOVASTATIN and potent competitive inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A reductase (HYDROXYMETHYLGLUTARYL COA REDUCTASES), which is the rate-limiting enzyme in cholesterol biosynthesis. It may also interfere with steroid hormone production. Due to the induction of hepatic LDL RECEPTORS, it increases breakdown of LDL CHOLESTEROL.. simvastatin : A member of the class of hexahydronaphthalenes that is lovastatin in which the 2-methylbutyrate ester moiety has been replaced by a 2,2-dimethylbutyrate ester group. It is used as a cholesterol-lowering and anti-cardiovascular disease drug.	2.08	1	0	delta-lactone; fatty acid ester; hexahydronaphthalenes; statin (semi-synthetic)	EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor; EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor; ferroptosis inducer; geroprotector; prodrug
itraconazole Itraconazole: A triazole antifungal agent that inhibits cytochrome P-450-dependent enzymes required for ERGOSTEROL synthesis.. itraconazole : An N-arylpiperazine that is cis-ketoconazole in which the imidazol-1-yl group is replaced by a 1,2,4-triazol-1-yl group and in which the actyl group attached to the piperazine moiety is replaced by a p-[(+-)1-sec-butyl-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl]phenyl group. A potent P-glycoprotein and CYP3A4 inhibitor, it is used as an antifungal drug for the treatment of various fungal infections, including aspergillosis, blastomycosis, candidiasis, chromoblastomycosis, coccidioidomycosis, cryptococcosis, histoplasmosis, and sporotrichosis.	2.07	1	0	aromatic ether; conazole antifungal drug; cyclic ketal; dichlorobenzene; dioxolane; N-arylpiperazine; triazole antifungal drug; triazoles	EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor; Hedgehog signaling pathway inhibitor; P450 inhibitor
fura-2 Fura-2: A fluorescent calcium chelating agent which is used to study intracellular calcium in tissues.	1.98	1	0
atorvastatin [no description available]	2.08	1	0	aromatic amide; dihydroxy monocarboxylic acid; monofluorobenzenes; pyrroles; statin (synthetic)	environmental contaminant; xenobiotic
3-iodobenzylguanidine 3-Iodobenzylguanidine: A guanidine analog with specific affinity for tissues of the sympathetic nervous system and related tumors. The radiolabeled forms are used as antineoplastic agents and radioactive imaging agents. (Merck Index, 12th ed) MIBG serves as a neuron-blocking agent which has a strong affinity for, and retention in, the adrenal medulla and also inhibits ADP-ribosyltransferase.	2.02	1	0	organoiodine compound
adenosine quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit	2.01	1	0	adenosines; purines D-ribonucleoside	analgesic; anti-arrhythmia drug; fundamental metabolite; human metabolite; vasodilator agent
3-n-butylphthalide 3-n-butylphthalide: isolated from phenolic part of Ligusticum wallichii Franch; structure given in first source	7.41	1	0	benzofurans
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.	1.94	1	0	aminoacridines; aromatic amine; tertiary amino compound	fluorochrome; histological dye
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.	2.02	1	0	one-carbon compound; perfluoroalkanesulfonic acid
4-vinylphenol 4-vinylphenol: RN given refers to cpd with locants as specified. 4-hydroxystyrene : A member of the class of phenols that is styrene carrying a hydroxy substituent at position 4.	2.05	1	0	phenols	human urinary metabolite; human xenobiotic metabolite
ethylenesulfonic acid [no description available]	2.07	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.	2.96	4	0	D-glucopyranose	epitope; mouse metabolite
n-methylnicotinamide N-methylnicotinamide: structure. N-methylnicotinamide : A pyridinecarboxamide that is nicotinamide in which one of the amide hydrogens is substituted by a methyl group.	2.08	1	0	pyridinecarboxamide	metabolite
thiazolyl blue thiazolyl blue: RN & II refers to bromide. 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide : The bromide salt of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium.	2.72	3	0	organic bromide salt	colorimetric reagent; dye
n-acetylaspartic acid N-acetyl-L-aspartic acid : An N-acyl-L-aspartic acid in which the acyl group is specified as acetyl.	2	1	0	N-acetyl-L-amino acid; N-acyl-L-aspartic acid	antioxidant; human metabolite; mouse metabolite; nutraceutical; rat metabolite
fluorexon fluorexon: structure	2.06	1	0	xanthene dye	fluorochrome
phosphoramidic acid phosphoramidic acid: urease inhibitor; RN given refers to parent cpd; structure; do not confuse with phosphoramidites, which are organophosphorus compounds	2.02	1	0	phosphoric acid derivative
tris(2,2'-bipyridine)ruthenium(II) tris(2,2'-bipyridyl)ruthenium(II): a fluorescent dye; structure in first source	2.48	2	0	ruthenium coordination entity	fluorochrome
fluorophosphate fluorophosphate: inhibits Phosphorylas phosphatase irreversibly; RN given refers to parent cpd	1.93	1	0	fluorine molecular entity; phosphoric acid derivative
glutathione disulfide Glutathione Disulfide: A GLUTATHIONE dimer formed by a disulfide bond between the cysteine sulfhydryl side chains during the course of being oxidized.	2.71	3	0	glutathione derivative; organic disulfide	Escherichia coli metabolite; mouse metabolite
2-acrylamido-2-methylpropanesulfonate 2-acrylamido-2-methylpropanesulfonate: for detection of alkaline phosphatase; RN given refers to parent cpd; do not confuse with AMPS cpd	2.1	1	0	organosulfonic acid
salicylhydroxamic acid [no description available]	2.4	2	0	hydroxamic acid; phenols	antibacterial drug; EC 1.11.2.2 (myeloperoxidase) inhibitor; EC 3.5.1.5 (urease) inhibitor; trypanocidal drug
1,7-phenanthroline [no description available]	3.3	6	0	phenanthroline
1h-imidazo(4,5-b)pyridine 1H-imidazo(4,5-b)pyridine: structure given in first source. 4-azabenzimidazole : The [4,5-b]-fused isomer of imidazopyridine.	2.21	1	0	imidazopyridine
triazoles Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.	2.7	3	0	1,2,3-triazole
1,5-difluoro-2,4-dinitrobenzene 1,5-difluoro-2,4-dinitrobenzene: structure	1.97	1	0
5-fluorosalicylic acid 5-fluorosalicylic acid: structure given in first source; product from action of alkaline phosphatase on 5-fluorosalicyl phosphate; forms highly fluorescent terbium ternary complex	2.11	1	0
trifluoroacetamide [no description available]	2.03	1	0
hydracrylic acid 3-hydroxypropionic acid : A 3-hydroxy monocarboxylic acid that is propionic acid in which one of the hydrogens attached to the terminal carbon is replaced by a hydroxy group.	2.85	3	0	3-hydroxy monocarboxylic acid; omega-hydroxy-short-chain fatty acid	Escherichia coli metabolite; human metabolite
rotenolone rotenolone: decomposition product of rotenone; RN given refers to (2 alpha,6a beta,12a beta)-isomer	3.11	1	0	organic molecular entity	metabolite
n,n-carbonyldiimidazole [no description available]	2.06	1	0
fluorodeoxyglucose f18 Fluorodeoxyglucose F18: The compound is given by intravenous injection to do POSITRON-EMISSION TOMOGRAPHY for the assessment of cerebral and myocardial glucose metabolism in various physiological or pathological states including stroke and myocardial ischemia. It is also employed for the detection of malignant tumors including those of the brain, liver, and thyroid gland. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1162)	2.01	1	0	2-deoxy-2-((18)F)fluoro-D-glucose; 2-deoxy-2-fluoro-aldehydo-D-glucose
4-aminobenzyl alcohol 4-aminobenzyl alcohol: structure	2.15	1	0
4(5)-phenylimidazole 4(5)-phenylimidazole: tautomeric cpd; cytochrome P450 14alpha-sterol demethylase, CYP51 antagonist	2.03	1	0
n-acetylglutamic acid N-acetylglutamic acid: RN given refers to (L)-isomer. N-acetyl-L-glutamic acid : An N-acyl-L-amino acid that is L-glutamic acid in which one of the amine hydrogens is substituted by an acetyl group.	1.96	1	0	N-acetyl-L-amino acid; N-acyl-L-glutamic acid	human metabolite; Saccharomyces cerevisiae metabolite
2-aminonicotinic acid 2-aminonicotinic acid: structure in first source. 2-aminonicotinic acid : An aminonicotinic acid in which the amino group is situated at position 2 of the pyridine ring.. aminonicotinic acid : An aromatic amino acid that is nicotinic acid in which one of the hydrogens attached to the pyridine ring is replaced by an amino group. A 'closed class'.	2.11	1	0	aminonicotinic acid; aminopyridine	metabolite
phosphonoacetamide phosphonoacetamide: inhibitors of carbamoyl phosphate and aspartate; RN from first source	2.4	2	0
3-aminopicolinic acid [no description available]	2.11	1	0
triphenylmethylphosphonium triphenylmethylphosphonium: RN given refers to parent cpd	1.98	1	0
malonamic acid malonamic acid: structure	1.97	1	0	beta-alanine derivative
2,5-furandicarboxylic acid furan-2,5-dicarboxylic acid : A member of the class of furans carrying two carboxy substituents at positions 2 and 5.	2.1	1	0	dicarboxylic acid; furans	human urinary metabolite
6-carboxyfluorescein 6-carboxyfluorescein: originally sold as 6-carboxyfluorescein, but commercial product is a mixture of two isomers; correct name is 5(6)-carboxyfluorescein	2.06	1	0	monocarboxylic acid
monomethyl succinate monomethyl succinate: RN given refers to parent cpd. monomethyl succinate : A dicarboxylic acid monoester that is succinic acid in which one of the carboxy groups has been converted to its methyl ester.	2.38	2	0	dicarboxylic acid monoester; hemisuccinate
rosiglitazone [no description available]	2.05	1	0	aminopyridine; thiazolidinediones	EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor; ferroptosis inhibitor; insulin-sensitizing drug
ferroin ferroin: RN given refers to parent cpd	8.15	5	0
bromates Bromates: Negative ions or salts derived from bromic acid, HBrO3.	4.06	14	0	bromine oxoanion; monovalent inorganic anion
coenzyme a [no description available]	3.57	9	0	adenosine 3',5'-bisphosphate	coenzyme; Escherichia coli metabolite; mouse metabolite
5-bromonicotinic acid 5-bromonicotinic acid: structure given in first source	2.11	1	0
goethite [no description available]	2.1	1	0
diflufenican diflufenican : A pyridinecarboxamide that is pyridine-3-carboxamide substituted by a 2,4-difluorophenyl group at the carbamoyl nitrogen and a 3-(trifluoromethyl)phenoxy group at position 2.	1.97	1	0	(trifluoromethyl)benzenes; aromatic ether; pyridinecarboxamide	carotenoid biosynthesis inhibitor; environmental contaminant; herbicide; xenobiotic
acetoacetyl coa [no description available]	2.13	1	0	3-oxo-fatty acyl-CoA	Escherichia coli metabolite; mouse metabolite
n-(4,4-diphenyl-3-butenyl)nipecotic acid N-(4,4-diphenyl-3-butenyl)nipecotic acid: structure given in first source	2	1	0	diarylmethane
propionyl-coenzyme a propionyl-coenzyme A: RN given refers to parent cpd	2.37	2	0	acyl-CoA	Escherichia coli metabolite; metabolite; mouse metabolite
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.	2.13	1	0	pyrroline
3,7-dimethyl-1-propargylxanthine 3,7-dimethyl-1-propargylxanthine: potent & selective in vivo antagonist of adenosine analogs	2.01	1	0
serine hydroxamate serine hydroxamate: RN given refers to (L)-isomer. serine hydroxamate : A hydroxamic acid obtained by formal condensation of the carboxy group of serine with the amino group of hydroxylamine.	2.05	1	0	hydroxamic acid; serine derivative	EC 6.1.1.11 (serine--tRNA ligase) inhibitor
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.	7.73	3	0	cobalt group element atom; metal allergen	micronutrient
chlorates Chlorates: Inorganic salts of chloric acid that contain the ClO3- ion.	2.05	1	0	chlorine oxoanion; monovalent inorganic anion
1,4-dihydropyridine [no description available]	2.05	1	0
sr141716 [no description available]	2.01	1	0	amidopiperidine; carbohydrazide; dichlorobenzene; monochlorobenzenes; pyrazoles	anti-obesity agent; appetite depressant; CB1 receptor antagonist
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).	2.45	2	0
fluorocitrate fluorocitrate: competitve inhibitor of aconitase; effects morphology of kidney tubules in fluorocitrate poisoning; RN given refers to cpd with unspecified isomeric designation	2.39	2	0	carbonyl compound
propionylcarnitine propionylcarnitine: RN given refers to cpd without isomeric designation	1.98	1	0	O-acylcarnitine	analgesic; antirheumatic drug; cardiotonic drug; human metabolite; peripheral nervous system drug
s-methylthiocitrulline S-methylthiocitrulline: a nitric oxide synthase inhibitor; structure in first source. S-methyl-L-thiocitrulline : An L-arginine derivative in which the guanidino NH2 group of L-arginine is replaced by a methylsufanyl group.	2.73	3	0	imidothiocarbamic ester; L-arginine derivative; L-ornithine derivative; non-proteinogenic L-alpha-amino acid	EC 1.14.13.39 (nitric oxide synthase) inhibitor; neuroprotective 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.	3.53	8	0
valerates Valerates: Derivatives of valeric acid, including its salts and esters.	1.98	1	0	short-chain fatty acid anion; straight-chain saturated fatty acid anion	plant metabolite
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	2.05	1	0	ketone
4'-phosphopantetheine D-pantetheine 4'-phosphate : Pantetheine 4'-phosphate with D (R) configuration at the 2' position.	1.96	1	0	pantetheine 4'-phosphate	prosthetic group
3-mercaptopicolinic acid 3-mercaptopicolinic acid: gluconeogenesis inhibitor; may also inhibit ATP-dependentphosphoenolpyruvate carboxykinase	1.97	1	0
caprylates Caprylates: Derivatives of caprylic acid. Included under this heading are a broad variety of acid forms, salts, esters, and amides that contain a carboxy terminated eight carbon aliphatic structure.. octanoate : A straight-chain saturated fatty acid anion that is the conjugate base of octanoic acid (caprylic acid); believed to block adipogenesis.	2.36	2	0	fatty acid anion 8:0; straight-chain saturated fatty acid anion	human metabolite; Saccharomyces cerevisiae metabolite
4,5-dioxovaleric acid 4,5-dioxopentanoic acid : A dioxo monocarboxylic acid consisting of a valeric acid core with the two oxo groups at the 4- and 5-positions.	1.98	1	0	dioxo monocarboxylic acid
5-fluoro-3-pyridinecarboxylic acid [no description available]	2.11	1	0
3,7,12-trihydroxycoprostanic acid [no description available]	1.98	1	0	12alpha-hydroxy steroid; 3alpha-hydroxy steroid; 7alpha-hydroxy steroid; cholestanoic acid; hydroxy monocarboxylic acid	human metabolite
tryptophan methyl ester tryptophan methyl ester: RN given refers to parent cpd(DL)-isomer	2	1	0
emoxypine succinate emoxypine succinate: has antihypoxic effects	2.05	1	0
1-adamantaneacetic acid [no description available]	2.02	1	0
peroxynitrous acid Peroxynitrous Acid: A potent oxidant synthesized by the cell during its normal metabolism. Peroxynitrite is formed from the reaction of two free radicals, NITRIC OXIDE and the superoxide anion (SUPEROXIDES).	2.02	1	0	nitrogen oxoacid
perchlorate perchlorate: the explosive component of rocket fuel; an environmental contaminant that disrupts THYROID HORMONES. perchlorate : A monovalent inorganic anion obtained by deprotonation of perchloric acid.	2.05	1	0	chlorine oxoanion; monovalent inorganic anion
fullerene c60 Fullerenes: A polyhedral CARBON structure composed of around 60-80 carbon atoms in pentagon and hexagon configuration. They are named after Buckminster Fuller because of structural resemblance to geodesic domes. Fullerenes can be made in high temperature such as arc discharge in an inert atmosphere.. fullerene : A compound composed solely of an even number of carbon atoms, which form a cage-like fused-ring polycyclic system with twelve five-membered rings and the rest six-membered rings. The term has been broadened to include any closed cage structure consisting entirely of three-coordinate carbon atoms.	3.76	10	0	fullerene	geroprotector
nnc 711 NNC 711: structure in first source	2.41	2	0
disuccinimidyl tartarate disuccinimidyl tartarate: RN given refers to (R-(R,R)-isomer); structure	1.97	1	0
delphinidin delphinidin: RN given refers to parent cpd;. delphinidin : An anthocyanidin cation consisting of benzopyrylium with hydroxy substituents at the 3-, 5- and 7-positions and a 3,4,5-trihydroxyphenyl group at the 2-position. It is a plant pigment responsible for the colours of the plants of the genera Viola and Delphinium.	2.42	2	0	5-hydroxyanthocyanidin	antineoplastic agent; biological pigment; plant metabolite
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.	2.01	1	0	5-hydroxyanthocyanidin	antioxidant; metabolite; neuroprotective agent
6h,8h-3,4-dihydropyrimido(4,5-c)(1,2)oxazin-7-one 6H,8H-3,4-dihydropyrimido(4,5-c)(1,2)oxazin-7-one: structure given in first source	2.06	1	0
ly 274614 LY 235959: RN refers to (3S-(3alpha,4aalpha,6beta,8aalpha))-isomer	1.98	1	0
5-(2,3,5-trichlorophenyl)pyrimidine-2,4-diamine ethane sulfonate [no description available]	1.99	1	0
ferene-s Ferene-S: used for serum iron determinations	2.04	1	0
carbon suboxide carbon suboxide: structure in first source	2.03	1	0	allenes; carbon oxide
duroquinol durohydroquinone : A member of the class of hydroquinones that is benzene-1,4-diol carrying four methyl groups at positions 2, 3, 5 and 6.	1.98	1	0	hydroquinones; methylbenzene	bacterial xenobiotic metabolite; volatile oil component
1,3,5-triaza-7-phosphaadamantane 1,3,5-triaza-7-phosphaadamantane: structure in first source	2.13	1	0
proline Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.	2.05	1	0	amino acid zwitterion; glutamine family amino acid; L-alpha-amino acid; proline; proteinogenic amino acid	algal metabolite; compatible osmolytes; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
cariporide cariporide: a selective sodium-hydrogen exchange subtype 1 inhibitor; structure in first source	2.04	1	0
naproxen Naproxen: An anti-inflammatory agent with analgesic and antipyretic properties. Both the acid and its sodium salt are used in the treatment of rheumatoid arthritis and other rheumatic or musculoskeletal disorders, dysmenorrhea, and acute gout.. naproxen : A methoxynaphthalene that is 2-methoxynaphthalene substituted by a carboxy ethyl group at position 6. Naproxen is a non-steroidal anti-inflammatory drug commonly used for the reduction of pain, fever, inflammation and stiffness caused by conditions such as osteoarthritis, kidney stones, rheumatoid arthritis, psoriatic arthritis, gout, ankylosing spondylitis, menstrual cramps, tendinitis, bursitis, and for the treatment of primary dysmenorrhea. It works by inhibiting both the COX-1 and COX-2 enzymes.	2.21	1	0	methoxynaphthalene; monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; gout suppressant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
hydroxyl radical Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.	3.31	6	0	oxygen hydride; oxygen radical; reactive oxygen species
cerium sulfate [no description available]	2.46	2	0
peroxymonosulfate peroxymonosulfate: oxidizing agent in prevention of tooth discoloration; RN given refers to ion(2-)	2.48	2	0	sulfur oxide; sulfur oxoanion
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.	2.39	2	0	carbodiimide
flaviolin flaviolin: isolated from mutants of Wangiella dermatitidis; structure given in first source. flaviolin : A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone having three hydroxy substituents placed at the 2-, 5- and 7-positions.	2.03	1	0
tetraphenylphosphonium tetraphenylphosphonium: RN given refers to parent cpd; structure. tetraphenylphosphonium : A polyatomic cation consisting of four phenyl groups attached to a central phosphonium.	2.37	2	0	heteroorganic entity; phosphorus molecular entity; polyatomic cation
ferrioxalate ferrioxalate: RN given refers to parent cpd	2.1	1	0
beta-methylcrotonylglycine beta-methylcrotonylglycine: structure. 3-methylcrotonyl glycine : An N-acylglycine in which the acyl group is specified as 3-methylbut-2-enoyl.	3.11	1	0	N-acylglycine	metabolite
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.	2.88	4	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).	2.25	1	0	amino acid zwitterion; angiotensin II	human metabolite
lignin Lignin: The most abundant natural aromatic organic polymer found in all vascular plants. Lignin together with cellulose and hemicellulose are the major cell wall components of the fibers of all wood and grass species. Lignin is composed of coniferyl, p-coumaryl, and sinapyl alcohols in varying ratios in different plant species. (From Merck Index, 11th ed). lignin : A polyphenylpropanoid derived from three monolignol monomers: trans-p-coumaryl alcohol, coniferol and trans-sinapyl alcohol. There is extensive cross-linking and no defined primary structure.	2.7	3	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	2.02	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.	2.03	1	0	divalent inorganic anion; phosphite ion
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.	2.21	1	0	aflatoxin; aromatic ether; aromatic ketone	carcinogenic agent; human metabolite
chlorite [no description available]	2.05	1	0	chlorine oxoanion; monovalent inorganic anion
cholic acid Cholic Acid: A major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion.. cholic acid : A bile acid that is 5beta-cholan-24-oic acid bearing three alpha-hydroxy substituents at position 3, 7 and 12.	1.98	1	0	12alpha-hydroxy steroid; 3alpha-hydroxy steroid; 7alpha-hydroxy steroid; bile acid; C24-steroid; trihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
3-nitrotyrosine 3-nitrotyrosine: RN given refers to parent cpd without isomeric designation. 3-nitrotyrosine : A nitrotyrosine comprising tyrosine having a nitro group at the 3-position on the phenyl ring.	3.25	6	0	2-nitrophenols; C-nitro compound; nitrotyrosine; non-proteinogenic alpha-amino acid
potassium bromide potassium bromide : A metal bromide salt with a K(+) counterion.	2.46	2	0	potassium salt
wortmannin [no description available]	2.31	1	0	acetate ester; cyclic ketone; delta-lactone; organic heteropentacyclic compound	anticoronaviral agent; antineoplastic agent; autophagy inhibitor; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor; geroprotector; Penicillium metabolite; radiosensitizing agent
5-aminonicotinic acid 5-aminonicotinic acid: an inhibitor of D-aspartate oxidase; structure in first source. 5-aminonicotinic acid : An aminonicotinic acid in which the amino group is situated at position 5 of the pyridine ring.	2.5	2	0	aminonicotinic acid; aminopyridine; aromatic amine	metabolite
dihydropyridines Dihydropyridines: Pyridine moieties which are partially saturated by the addition of two hydrogen atoms in any position.	2.05	1	0
carboplatin [no description available]	2.17	1	0
glycogen glycogen : A polydisperse, highly branched glucan composed of chains of D-glucopyranose residues in alpha(1->4) glycosidic linkage, joined together by alpha(1->6) glycosidic linkages. A small number of alpha(1->3) glycosidic linkages and some cumulative alpha(1->6) links also may occur. The branches in glycogen typically contain 8 to 12 glucose residues.	2.35	2	0
glycerate 1,3-biphosphate 3-phospho-D-glyceroyl dihydrogen phosphate : The (R)-enantiomer of 3-phosphoglyceroyl dihydrogen phosphate.	2.03	1	0	2,3-bisphosphoglyceric acid; acyl monophosphate	Escherichia coli metabolite; mouse metabolite
elastin [no description available]	3.43	1	1	oligopeptide
naringenin (S)-naringenin : The (S)-enantiomer of naringenin.	2.6	1	0	(2S)-flavan-4-one; naringenin	expectorant; plant metabolite
pantetheine Pantetheine: An intermediate in the pathway of coenzyme A formation in mammalian liver and some microorganisms.. pantetheine : An amide obtained by formal condensation of the carboxy group of pantothenic acid and the amino group of cysteamine.	1.96	1	0	pantetheines; thiol	human metabolite; metabolite; mouse metabolite
cysteinylglycine cysteinylglycine: RN given refers to (L)-isomer; RN for cpd without isomeric designation not in Chemlne 7/13/83. L-cysteinylglycine : A dipeptide consisting of glycine having an L-cysteinyl attached to its alpha-amino group. It is an intermediate metabolite in glutathione metabolism.	2.25	1	0	dipeptide zwitterion; dipeptide	Escherichia coli metabolite; human metabolite; Saccharomyces cerevisiae 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.	2.88	4	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
tartaric acid tartaric acid: RN given refers to cpd with unspecified isomeric designation. D-tartaric acid : The D-enantiomer of tartaric acid.	8.81	11	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.	2.39	2	0	guanidines; L-arginine derivative; N-nitro compound; non-proteinogenic L-alpha-amino acid
actinorhodin actinorhodin: structure. actinorhodin : A member of the class of benzoisochromanequinone that is produced by Streptomyces coelicolor A3(2) and exhibits antibiotic activity.	2.03	1	0
11alpha,13-dihydrohelenalin [no description available]	1.96	1	0	sesquiterpene lactone
maleic acid maleic acid: RN given refers to parent cpd(Z)-isomer which is maleic acid; all RR's given refer to (Z)-isomer; (E)-isomer is fumaric acid. maleic acid : A butenedioic acid in which the double bond has cis- (Z)-configuration.	8.61	9	0	butenedioic acid	algal metabolite; mouse metabolite; plant metabolite
acetyl coenzyme a Acetyl Coenzyme A: Acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent.	3.47	8	0	acyl-CoA	acyl donor; coenzyme; effector; fundamental metabolite
fumaric acid fumaric acid: see also record for ferrous fumarate; use FUMARATES for general fumaric acid esters. fumaric acid : A butenedioic acid in which the C=C double bond has E geometry. It is an intermediate metabolite in the citric acid cycle.	3.89	12	0	butenedioic acid	food acidity regulator; fundamental metabolite; geroprotector
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.	2.66	3	0	octadec-9-enoic acid	antioxidant; Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; Escherichia coli metabolite; mouse metabolite; plant metabolite; solvent
tacrolimus Tacrolimus: A macrolide isolated from the culture broth of a strain of Streptomyces tsukubaensis that has strong immunosuppressive activity in vivo and prevents the activation of T-lymphocytes in response to antigenic or mitogenic stimulation in vitro.. tacrolimus (anhydrous) : A macrolide lactam containing a 23-membered lactone ring, originally isolated from the fermentation broth of a Japanese soil sample that contained the bacteria Streptomyces tsukubaensis.	2.46	2	0	macrolide lactam	bacterial metabolite; immunosuppressive agent
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.	2.06	1	0	icosapentaenoic acid; omega-3 fatty acid	anticholesteremic drug; antidepressant; antineoplastic agent; Daphnia galeata metabolite; fungal metabolite; micronutrient; mouse metabolite; nutraceutical
mupirocin Mupirocin: A topically used antibiotic from a strain of Pseudomonas fluorescens. It has shown excellent activity against gram-positive staphylococci and streptococci. The antibiotic is used primarily for the treatment of primary and secondary skin disorders, nasal infections, and wound healing.. mupirocin : An alpha,beta-unsaturated ester resulting from the formal condensation of the alcoholic hydroxy group of 9-hydroxynonanoic acid with the carboxy group of (2E)-4-[(2S)-tetrahydro-2H-pyran-2-yl]-3-methylbut-2-enoic acid in which the tetrahydropyranyl ring is substituted at positions 3 and 4 by hydroxy groups and at position 5 by a {(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl}methyl group. Originally isolated from the Gram-negative bacterium Pseudomonas fluorescens, it is used as a topical antibiotic for the treatment of Gram-positive bacterial infections.	2.04	1	0	alpha,beta-unsaturated carboxylic ester; epoxide; monocarboxylic acid; oxanes; secondary alcohol; triol	antibacterial drug; bacterial metabolite; protein synthesis inhibitor
stigmatellin stigmatellin: isolated from myxobacterium Stigmatella aurantiaca; structure in first source. stigmatellin A : A member of the class of chromones that is isolated from Stigmatella aurantiaca Sg a15.	2.03	1	0	aromatic ether; chromones; olefinic compound; phenols	bacterial metabolite; quinol oxidation site inhibitor
imidazolidines [no description available]	2.11	1	0	azacycloalkane; imidazolidines; saturated organic heteromonocyclic parent
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).	2.01	1	0
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).	2.05	1	0	flavin; vitamin B2	anti-inflammatory agent; antioxidant; cofactor; Escherichia coli metabolite; food colouring; fundamental metabolite; human urinary metabolite; mouse metabolite; photosensitizing agent; plant metabolite
sodium bicarbonate Sodium Bicarbonate: A white, crystalline powder that is commonly used as a pH buffering agent, an electrolyte replenisher, systemic alkalizer and in topical cleansing solutions.	1.97	1	0	one-carbon compound; organic sodium salt	antacid; food anticaking agent
potassium bicarbonate potassium hydrogencarbonate : A potassium salt that is the monopotassium salt of carbonic acid. It has fungicidal properties and is used in organic farming for the control of powdery mildew and apple scab.	1.94	1	0	organic salt; potassium salt	antifungal agrochemical; buffer; food acidity regulator; raising agent
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.	2.36	2	0	organic sodium salt	NMR chemical shift reference compound
crotonic acid crotonic acid: a stereospecific unsaturated carboxylic acid found in CROTON OIL. butenoic acid : Any C4, straight-chain fatty acid containing one double bond.. crotonic acid : A but-2-enoic acid with a trans- double bond at C-2. It has been isolated from Daucus carota.	2.08	1	0	2-butenoic acid	plant metabolite
3-coumaric acid 3-coumaric acid: RN given refers to cpd without isomeric designation in Chemline. trans-3-coumaric acid : A 3-coumaric acid that is phenol substituted with trans-2-propenoic acid at position C-3.. 3-coumaric acid : A monohydroxycinnamic acid in which the hydroxy substituent is located at C-3 of the phenyl ring.	2.08	1	0	3-coumaric acid
trans-4-coumaric acid hydroxycinnamic acid : Any member of the class of cinnamic acids carrying one or more hydroxy substituents.. trans-4-coumaric acid : The trans-isomer of 4-coumaric acid.. 4-coumaric acid : A coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring.	2.6	1	0	4-coumaric acid	food component; mouse metabolite; plant metabolite
glycosides [no description available]	2.67	3	0
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	2.04	1	0	stilbene
phenyl-n-tert-butylnitrone phenyl-N-tert-butylnitrone: a spin-trapping agent	2.92	4	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	1	0	flavin adenine dinucleotide; vitamin B2	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; prosthetic group
cannabidiol Cannabidiol: Compound isolated from Cannabis sativa extract.. cannabidiol : An cannabinoid that is cyclohexene which is substituted by a methyl group at position 1, a 2,6-dihydroxy-4-pentylphenyl group at position 3, and a prop-1-en-2-yl group at position 4.	2.07	1	0	olefinic compound; phytocannabinoid; resorcinols	antimicrobial agent; plant metabolite
malonyl coenzyme a Malonyl Coenzyme A: A coenzyme A derivative which plays a key role in the fatty acid synthesis in the cytoplasmic and microsomal systems.. omega-carboxyacyl-CoA : An acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with one of the carboxy groups of any alpha,omega-dicarboxylic acid.	6.07	22	0	malonyl-CoAs	EC 2.3.1.21 (carnitine O-palmitoyltransferase) inhibitor; Escherichia coli metabolite; metabolite; mouse metabolite
pyrophosphate Diphosphates: Inorganic salts of phosphoric acid that contain two phosphate groups.	2.71	3	0	diphosphate ion
sesquiterpenes [no description available]	2.02	1	0
caffeic acid trans-caffeic acid : The trans-isomer of caffeic acid.	7.93	4	0	caffeic acid	geroprotector; mouse metabolite
pseudoginsenoside f11 [no description available]	2.08	1	0
thiourea Thiourea: A photographic fixative used also in the manufacture of resins. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), this substance may reasonably be anticipated to be a carcinogen (Merck Index, 9th ed). Many of its derivatives are ANTITHYROID AGENTS and/or FREE RADICAL SCAVENGERS.. thiourea : The simplest member of the thiourea class, consisting of urea with the oxygen atom substituted by sulfur.	2.95	4	0	one-carbon compound; thioureas; ureas	antioxidant; chromophore
fumonisin b1 fumonisin B1: isolated from Fusarium moniliforme MRC 826; structure given in first source; has cancer-promoting activity; inhibits ceramide synthase. fumonisin B1 : A diester that results from the condensation of the 1-carboxy groups of two molecules of propane-1,2,3-tricarboxylic acid with hydroxy groups at positions 14 and 15 of (2S,3S,5R,10R,12S,14S,15R,16R)-2-amino-12,16-dimethylicosane-3,5,10,14,15-pentol.	2.21	1	0	diester; fumonisin; primary amino compound; triol	carcinogenic agent; metabolite
nadp [no description available]	3.22	6	0
1,1-diphenyl-2-picrylhydrazyl 1,1-diphenyl-2-picrylhydrazyl: A diphenyl picrate; the ability to decolorize this stable radical indicates reactivity of tested compounds (Banda, Anal Chem 46:1772-7 1974)	2.04	1	0
valinomycin Valinomycin: A cyclododecadepsipeptide ionophore antibiotic produced by Streptomyces fulvissimus and related to the enniatins. It is composed of 3 moles each of L-valine, D-alpha-hydroxyisovaleric acid, D-valine, and L-lactic acid linked alternately to form a 36-membered ring. (From Merck Index, 11th ed) Valinomycin is a potassium selective ionophore and is commonly used as a tool in biochemical studies.. valinomycin : A twelve-membered cyclodepsipeptide composed of three repeating D-alpha-hydroxyisovaleryl-D-valyl-L-lactoyl-L-valyl units joined in sequence. An antibiotic found in several Streptomyces strains.	2.88	4	0	cyclodepsipeptide; macrocycle	antimicrobial agent; antiviral agent; bacterial metabolite; potassium ionophore
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.	2.01	1	0	barbiturates	anticonvulsant; drug allergen; environmental contaminant; intravenous anaesthetic; sedative; xenobiotic
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.	2.02	1	0
lithium Lithium: An element in the alkali metals family. It has the atomic symbol Li, atomic number 3, and atomic weight [6.938; 6.997]. Salts of lithium are used in treating BIPOLAR DISORDER.	2.01	1	0	alkali metal atom
ethylenediamine platinum(ii) malonate [no description available]	1.96	1	0
sr 144528 SR 144528: a CB2 cannabinoid receptor antagonist; structure in first source. SR 144528 : A secondary carboxamide resulting from the formal condensation of the carboxy group of 5-(4-chloro-3-methylphenyl)-1-(4-methylbenzyl)-1H-pyrazole-3-carboxylic acid with the amino group of (1S,2S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-amine. A potent and selective cannabinoid receptor type 2 (CB2 receptor) inverse agonist (Ki = 0.6 nM).	2.05	1	0	bridged compound; monochlorobenzenes; pyrazoles; secondary carboxamide	CB2 receptor antagonist; EC 2.3.1.26 (sterol O-acyltransferase) inhibitor
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.	2.76	3	0
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	1.98	1	0	naphthalenes; sulfonic acid derivative
4-nitrocatechol 4-nitrocatechol : A member of the class of catechols that is benzene-1,2-diol substituted by a nitro group at position 4.It is the by-product of the hydroxylation of p-nitrophenol.	2.05	1	0	C-nitro compound; catechols	human xenobiotic metabolite; lipoxygenase inhibitor
3-nitrophenylhydrazine 3-nitrophenylhydrazine: structure in first source	2.15	1	0
2-ethynylaniline 2-ethynylaniline: structure in first source	2.05	1	0
naphthoquinones Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.	2.67	3	0
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.	2.39	2	0	organic cation; xanthene dye	fluorochrome
4-nitrobenzohydroxamic acid 4-nitrobenzohydroxamic acid: structure in first source	2.05	1	0
ex 527 6-chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxamide: structure in first source. 6-chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxamide : A member of the class of carbazoles that is 2,3,4,9-tetrahydro-1H-carbazole which is substituted at position 1 by an aminocarbohyl group and at position 6 by a chlorine.	2.1	1	0	carbazoles; monocarboxylic acid amide; organochlorine compound
bilirubin [no description available]	2	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.	2.46	2	0	prostaglandins E	human metabolite; mouse metabolite; oxytocic
sterigmatocystin [no description available]	2.02	1	0	sterigmatocystins	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.	2.02	1	0	carotenoid beta-end derivative; cyclic carotene	antioxidant; biological pigment; cofactor; ferroptosis inhibitor; human metabolite; mouse metabolite; plant metabolite; provitamin A
glutaconic acid glutaconic acid: RN given refers to parent cpd without isomeric designation; structure. glutaconic acid : A pentenedioic acid that is pent-2-ene substituted by carboxy groups at positions 1 and 5.. (E)-glutaconic acid : The (E)-isomer of glutaconic acid.	2.05	1	0	glutaconic acid
rutin Hydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders.	1.97	1	0	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite
montelukast montelukast: a leukotriene D4 receptor antagonist	7.05	1	0	aliphatic sulfide; monocarboxylic acid; quinolines	anti-arrhythmia drug; anti-asthmatic drug; leukotriene antagonist
astaxanthine astaxanthine: a keto form of carotene; pigment in flesh of Scottish salmon (Salmo salar) crustacoa-lobster (Homarus gammarus, flamingo feathers; structure; a carotenoid without vitamin A activity, has shown anti-oxidant and anti-inflammatory activities. astaxanthin : A carotenone that consists of beta,beta-carotene-4,4'-dione bearing two hydroxy substituents at positions 3 and 3' (the 3S,3'S diastereomer). A carotenoid pigment found mainly in animals (crustaceans, echinoderms) but also occurring in plants. It can occur free (as a red pigment), as an ester, or as a blue, brown or green chromoprotein.	2.02	1	0	carotenol; carotenone	animal metabolite; anticoagulant; antioxidant; food colouring; plant metabolite
oleuropein oleuropein: iridoid isolated from leaves and fruit of Olea and Ligustrum (Oleaceae). oleuropein : A secoiridoid glycoside that is the methyl ester of 3,4-dihydro-2H-pyran-5-carboxylic acid which is substituted at positions 2, 3, and 4 by hydroxy, ethylidene, and carboxymethyl groups, respectively and in which the anomeric hydroxy group at position 2 has been converted into its beta-D-glucoside and the carboxylic acid moiety of the carboxymethyl substituent has been converted to the corresponding 3,4-dihydroxyphenethyl ester (the 2S,3E,4S stereoisomer). The most important phenolic compound present in olive cultivars.	2.01	1	0	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.	2.21	1	0	macrolide; resorcinols	fungal metabolite; mycoestrogen
cynarine cynarine: active principle of the artichoke; functions primarily as a cholagogue and choleretic and also as antilipemic agent	2.01	1	0	alkyl caffeate ester; quinic acid	plant metabolite
echinacoside echinacoside: from Buddleja species; has antihepatotoxic activity	2.01	1	0	oligosaccharide
maytansine Maytansine: An ansa macrolide isolated from the MAYTENUS genus of East African shrubs.. maytansine : An organic heterotetracyclic compound and 19-membered macrocyclic lactam antibiotic originally isolated from the Ethiopian shrub Maytenus serrata but also found in other Maytenus species. It exhibits cytotoxicity against many tumour cell lines.	2.49	2	0	alpha-amino acid ester; carbamate ester; epoxide; maytansinoid; organic heterotetracyclic compound; organochlorine compound	antimicrobial agent; antimitotic; antineoplastic agent; plant metabolite; tubulin modulator
soraphen a [no description available]	2.03	1	0	cyclic hemiketal; ether; macrolide; olefinic compound	bacterial metabolite; EC 6.4.1.2 (acetyl-CoA carboxylase) inhibitor; teratogenic agent
coenzyme q10 coenzyme Q10: Ubiquinone ring with a chain of 10 isoprene units; redox equilibrium with ubiqunol serving in mitochondrial inner membrane to transfer electrons; presence during reconstitution of acetylcholine receptor into phospholipid vesicles yields vesicles active in catalyzing carbamylcholine-sensitive Na+ flux; coenzyme Q10 depletion has been noted with use of statins. coenzyme Q10 : A ubiquinone having a side chain of 10 isoprenoid units. In the naturally occurring isomer, all isoprenyl double bonds are in the E- configuration.	4.29	4	0	ubiquinones	antioxidant; ferroptosis inhibitor; human metabolite
anandamide anandamide : An N-acylethanolamine 20:4 resulting from the formal condensation of carboxy group of arachidonic acid with the amino group of ethanolamine.	2.03	1	0	endocannabinoid; N-acylethanolamine 20:4	human blood serum metabolite; neurotransmitter; vasodilator agent
picromycin picromycin: structure. pikromycin : A macrolide antibiotic that is biosynthesised by Streptomyces venezuelae.	2.04	1	0	enone; macrolide antibiotic; monosaccharide derivative	bacterial metabolite
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.	2.6	1	0	epoxide; monocarboxylic acid amide	antifungal agent; antiinfective agent; antilipemic drug; antimetabolite; antimicrobial agent; fatty acid synthesis inhibitor
4-acetamido-4'-isothiocyanatostilbene-2,2'-disulfonic acid 4-Acetamido-4'-isothiocyanatostilbene-2,2'-disulfonic Acid: A non-penetrating amino reagent (commonly called SITS) which acts as an inhibitor of anion transport in erythrocytes and other cells.	1.97	1	0	stilbenoid
glyceryl 2-arachidonate glyceryl 2-arachidonate: binds to cannabinoid receptors; structure in first source. 2-arachidonoylglycerol : An endocannabinoid and an endogenous agonist of the cannabinoid receptors (CB1 and CB2). It is an ester formed from omega-6-arachidonic acid and glycerol.	2.08	1	0	2-acylglycerol 20:4; endocannabinoid	human metabolite
cis-vaccenic acid cis-vaccenic acid: isomer of oleic acid. vaccenic acid : An octadecenoic acid having a double bond at position 11; and which can occur in cis- or trans- configurations.. cis-vaccenic acid : The cis isomer of vaccenic acid.	1.97	1	0	vaccenic acid
arachidonyl-2-chloroethylamide arachidonyl-2-chloroethylamide: a potent and selective agonist of the neuronal cannabinoid receptor; structure in first source. arachidonyl-2'-chloroethylamide : A fatty amide obtained by the formal condensation of arachidonic acid with 2-chloroethanamine. It is a potent agonist of the CB1 receptor (Ki = 1.4 nM) and also has a low affinity for the CB2 receptor (Ki = 3100 nM).	2.05	1	0	fatty amide; organochlorine compound; secondary carboxamide; synthetic cannabinoid	CB1 receptor agonist; CB2 receptor agonist; neuroprotective agent
1,2-oleoylphosphatidylcholine 1,2-oleoylphosphatidylcholine: RN given refers to (Z,Z)-isomer. dioleoyl phosphatidylcholine : A phosphatidylcholine in which the phosphatidyl acyl groups are both oleoyl.	2.25	1	0	phosphatidylcholine(1+)
lead Lead: A soft, grayish metal with poisonous salts; atomic number 82, atomic weight 207.2, symbol Pb.	2.44	2	0	carbon group element atom; elemental lead; metal atom	neurotoxin
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.	2.37	2	0	1,1'-azobis(N,N-dimethylformamide)
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.	2.4	2	0	alkaline earth metal atom; elemental barium
ethyl fumarate [no description available]	1.99	1	0
aluminum Aluminum: A metallic element that has the atomic number 13, atomic symbol Al, and atomic weight 26.98.	2.41	2	0	boron group element atom; elemental aluminium; metal atom
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.	2.41	2	0	alkaline earth metal atom
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).	3.36	7	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)	3.06	5	0	metalloid atom; pnictogen	micronutrient
sulfur Sulfur: An element that is a member of the chalcogen family. It has an atomic symbol S, atomic number 16, and atomic weight [32.059; 32.076]. It is found in the amino acids cysteine and methionine.	2.74	3	0	chalcogen; nonmetal atom	macronutrient
puerarin [no description available]	2.01	1	0	C-glycosyl compound; isoflavonoid
deoxyribose [no description available]	2.04	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-)	4.13	16	0	butenedioate; C4-dicarboxylate	human metabolite; metabolite; Saccharomyces cerevisiae metabolite
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	2.91	4	0	cysteinium	fundamental metabolite
isophthalate isophthalate: RN given refers to parent cpd	1.98	1	0	dicarboxylic acid dianion
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.	2.13	1	0	monoatomic phosphorus; nonmetal atom; pnictogen	macronutrient
oxyhyponitrite oxyhyponitrite: nitrosating agent; structure given in first source; RN given refers to parent acid	2.02	1	0
epicinchonine epicinchonine: structure in first source. cinchonine : Cinchonan in which a hydrogen at position 9 is substituted by hydroxy (S configuration). It occurs in the bark of most varieties of Cinchona shrubs, and is frequently used for directing chirality in asymmetric synthesis.	2.03	1	0	cinchona alkaloid
n-tert-butyl-(2-sulfophenyl)nitrone N-tert-butyl-(2-sulfophenyl)nitrone: Neuroprotectant	1.98	1	0
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.	2.44	2	0	ammonium salt; inorganic sulfate salt	fertilizer
4,4'-diisothiocyanostilbene-2,2'-disulfonic acid 4,4'-Diisothiocyanostilbene-2,2'-Disulfonic Acid: An inhibitor of anion conductance including band 3-mediated anion transport.	1.97	1	0
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.	2.03	1	0	chalcogen; nonmetal atom	micronutrient
radium Radium: A radioactive element of the alkaline earth series of metals. It has the atomic symbol Ra and atomic number 88. Radium is the product of the disintegration of URANIUM and is present in pitchblende and all ores containing uranium. It is used clinically as a source of beta and gamma-rays in radiotherapy, particularly BRACHYTHERAPY.	2.03	1	0	alkaline earth metal atom
oxalates Oxalates: Derivatives of OXALIC ACID. Included under this heading are a broad variety of acid forms, salts, esters, and amides that are derived from the ethanedioic acid structure.	9.23	18	0
dizocilpine maleate Dizocilpine Maleate: A potent noncompetitive antagonist of the NMDA receptor (RECEPTORS, N-METHYL-D-ASPARTATE) used mainly as a research tool. The drug has been considered for the wide variety of neurodegenerative conditions or disorders in which NMDA receptors may play an important role. Its use has been primarily limited to animal and tissue experiments because of its psychotropic effects.. dizocilpine maleate : A maleate salt obtained by reaction of dizocilpine with one equivalent of maleic acid.	4.19	17	0	maleate salt; tetracyclic antidepressant	anaesthetic; anticonvulsant; neuroprotective agent; nicotinic antagonist; NMDA receptor antagonist
antimycin a Antimycin A: An antibiotic substance produced by Streptomyces species. It inhibits mitochondrial respiration and may deplete cellular levels of ATP. Antimycin A1 has been used as a fungicide, insecticide, and miticide. (From Merck Index, 12th ed). antimycin A : A nine-membered bis-lactone having methyl substituents at the 2- and 6-positions, an n-hexyl substituent at the 8-position, an acyloxy substituent at the 7-position and an aroylamido substituent at the 3-position. It is produced by Streptomyces bacteria and has found commercial use as a fish poison.	3.93	13	0	amidobenzoic acid
bongkrekic acid Bongkrekic Acid: An antibiotic produced by Pseudomonas cocovenenans. It is an inhibitor of MITOCHONDRIAL ADP, ATP TRANSLOCASES. Specifically, it blocks adenine nucleotide efflux from mitochondria by enhancing membrane binding.. bongkrekic acid : A tricarboxylic acid that is docosa-2,4,8,10,14,18,20-heptaenedioic acid substituted at positions 2 ,5 and 17 by methyl groups, at positions 6 by a methoxy group and at position 20 by a carboxymethyl group. It is produced by the bacterium Burkholderia gladioli and implicated in outbreaks of food-borne illness involving coconut and corn-based products in Indonesia and China.	2.43	2	0	ether; olefinic compound; tricarboxylic acid	apoptosis inhibitor; ATP/ADP translocase inhibitor; bacterial metabolite; EC 2.5.1.18 (glutathione transferase) inhibitor; toxin
papulacandin b papulacandin B: from Papularia sphaerosperma; inhibits growth of Candida albicans. papulacandin B : A papulacandin that is papulacandin A in which the (2E,4E)-deca-2,4-dienoyl chain at the O-(6') position is replaced by a (2E,4Z,6E)-8-hydroxydeca-2,4,6-trienoyl chain. It is the major carbohydrate-containing antibiotic from the deuteromycetous fungus Papularia sphaerosperma which shows potent antifungal activity against Candida albicans.	1.99	1	0
myxothiazol myxothiazol: strobilurin analogue; methoxyacrylamide derivative; antifungal antibiotic from Myxococcus fulvus; structure given in first source. myxothiazol : A 2,4'-bi-1,3-thiazole substituted at the 4-position with a (1E,3S,4R,5E)-7-amino-3,5-dimethoxy-4-methyl-7-oxohepta-1,5-dien-1-yl] group and at the 2'-position with a (2S,3E,5E)-7-methylocta-3,5-dien-2-yl group. It is an inhibitor of coenzyme Q - cytochrome c reductase.	1.97	1	0
bacteriochlorophylls Bacteriochlorophylls: Pyrrole containing pigments found in photosynthetic bacteria.	2	1	0
beta-escin [no description available]	2.31	1	0
bromopyruvate [no description available]	2.31	1	0	2-oxo monocarboxylic acid anion
sun [no description available]	2.08	1	0
phosphocreatine Phosphocreatine: An endogenous substance found mainly in skeletal muscle of vertebrates. It has been tried in the treatment of cardiac disorders and has been added to cardioplegic solutions. (Reynolds JEF(Ed): Martindale: The Extra Pharmacopoeia (electronic version). Micromedex, Inc, Englewood, CO, 1996). phosphagen : Any of a group of guanidine or amidine phosphates that function as storage depots for high-energy phosphate in muscle with the purpose of regenerating ATP from ADP during muscular contraction.. N-phosphocreatine : A phosphoamino acid consisting of creatine having a phospho group attached at the primary nitrogen of the guanidino group.	2.05	1	0	phosphagen; phosphoamino acid	human metabolite; mouse metabolite
mannich bases Mannich Bases: Ketonic amines prepared from the condensation of a ketone with formaldehyde and ammonia or a primary or secondary amine. A Mannich base can act as the equivalent of an alpha,beta unsaturated ketone in synthesis or can be reduced to form physiologically active amino alcohols.	2.03	1	0
nikkomycin [no description available]	1.99	1	0
rivaroxaban Rivaroxaban: A morpholine and thiophene derivative that functions as a FACTOR XA INHIBITOR and is used in the treatment and prevention of DEEP-VEIN THROMBOSIS and PULMONARY EMBOLISM. It is also used for the prevention of STROKE and systemic embolization in patients with non-valvular ATRIAL FIBRILLATION, and for the prevention of atherothrombotic events in patients after an ACUTE CORONARY SYNDROME.. rivaroxaban : A monocarboxylic acid amide obtained by formal condensation of the carboxy group of 5-chlorothiophene-2-carboxylic acid with the amino group of 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one. An anticoagulant used for prophylaxis of venous thromboembolism in patients with knee or hip replacement surgery.	7.21	1	0	aromatic amide; lactam; monocarboxylic acid amide; morpholines; organochlorine compound; oxazolidinone; thiophenes	anticoagulant; EC 3.4.21.6 (coagulation factor Xa) inhibitor
ubiquinol ubiquinol: reduced forms of ubiquinone; see also record for ubiquinol 10. ubiquinol-10 : A ubiquinol in which the polyprenyl substituent is decaprenyl.	3.11	1	0	polyprenylhydroquinone; ubiquinol	biomarker; metabolite
ombuoside ombuoside: structure given in first source; isolated from Gynostemma pentaphyllum	1.97	1	0
alpha-synuclein alpha-Synuclein: A synuclein that is a major component of LEWY BODIES and plays a role in SYNUCLEINOPATHIES, neurodegeneration and neuroprotection.	2.03	1	0
aeruginosin 298-a aeruginosin 298-A: structure in first source	2.02	1	0
gigantecin gigantecin: structure given in first source; isolated from the stem bark of Goniothalamus gigateus; a tetrahydroxy-di-tetrahydrofuran fatty acid gamma-lactone (acetogenin)	2.06	1	0
3-dihydroxy-6-methyl-7-(phenylmethyl)-4-propylnaphthalene-1-carboxylic acid 3-dihydroxy-6-methyl-7-(phenylmethyl)-4-propylnaphthalene-1-carboxylic acid: inhibits lactate dehydrogenase A	2.07	1	0
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.	1.98	1	0	nystatins
marizomib marizomib: a proteasome inhibitor from a marine bacterium Salinospora; structure in first source	2.04	1	0	beta-lactone; gamma-lactam; organic heterobicyclic compound; organochlorine compound; salinosporamide	antineoplastic agent; proteasome inhibitor
potassium cyanate potassium cyanate: RN given refers to cpd with MF of K-CHNO	2.05	1	0	cyanate salt; one-carbon compound	herbicide
hu 308 HU 308: a specific agonist for CB(2), a peripheral cannabinoid receptor; structure in first source. HU-308 : A carbobicyclic compound that is bicyclo[3.1.1]hept-2-ene which is substituted by a hydroxymethyl group at position 2, a 2,6-dimethoxy-4-(2-methyloctan-2-yl)phenyl group at position 4, and two methyl groups at position 6 (the 1S,4S,5S stereoisomer). A highly selective and effective cannabinoid type-2 agonist and the enantiomer of HU-433.	2.05	1	0	aromatic ether; bridged compound; carbobicyclic compound; primary allylic alcohol; synthetic cannabinoid	anti-inflammatory agent; antihypertensive agent; apoptosis inhibitor; bone density conservation agent; CB2 receptor agonist
alpha-Neup5Ac-(2->3)-beta-D-Galp-(1->4)-[alpha-L-Fucp-(1->3)]-D-GlcpNAc Sialyl Lewis X Antigen: A sialylated version of Lewis X antigen expressed on cell surfaces. It is a ligand for SELECTINS.. alpha-Neup5Ac-(2->3)-beta-D-Galp-(1->4)-[alpha-L-Fucp-(1->3)]-D-GlcpNAc : A branched amino tetrasaccharide consisting of a sialyl residue, linked (2->3) to a galactosyl residue that in turn is linked (1->4) to a glucosaminyl residue, which is also carrying a fucosyl residue at the 3-position.	2	1	0	amino tetrasaccharide; glucosamine oligosaccharide	epitope
palmitoylcarnitine Palmitoylcarnitine: A long-chain fatty acid ester of carnitine which facilitates the transfer of long-chain fatty acids from cytoplasm into mitochondria during the oxidation of fatty acids.. O-palmitoyl-L-carnitine : An O-acyl-L-carnitine in which the acyl group is specified as palmitoyl (hexadecanoyl).	2.9	4	0	O-palmitoylcarnitine; saturated fatty acyl-L-carnitine	EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; human metabolite; mouse metabolite
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.	2.68	3	0	benzoxazole
virginiamycin Virginiamycin: A cyclic polypeptide antibiotic complex from Streptomyces virginiae, S. loidensis, S. mitakaensis, S. pristina-spiralis, S. ostreogriseus, and others. It consists of 2 major components, VIRGINIAMYCIN FACTOR M1 and virginiamycin Factor S1. It is used to treat infections with gram-positive organisms and as a growth promoter in cattle, swine, and poultry.. virginiamycin : A mixture of cyclic polypeptide streptogramin antibiotics produced by Streptomyces virginiae, S. loidensis, S. mitakaensis, S. pristina-spiralis, S. ostreogriseus, and others. The two major components are virginiamycin M1 (also known as pristinamycin IIA) and virginiamycin S1. Virginiamycin has been widely used as a growth promotion agent in livestock and has been to have bacteriostatic activity against Gram-positive organisms such as staphylococci and streptococci.	2.6	1	0
acid phosphatase Acid Phosphatase: An enzyme that catalyzes the conversion of an orthophosphoric monoester and water to an alcohol and orthophosphate. EC 3.1.3.2.	1.94	1	0
adenosine monophosphate adenosine 5'-monophosphate(2-) : A nucleoside 5'-monophosphate(2-) that results from the removal of two protons from the phosphate group of adenosine 5'-monophosphate (AMP).	2.07	1	0	nucleoside 5'-monophosphate(2-)	cofactor; fundamental metabolite; human metabolite
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	4.27	19	0	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
desmosine Desmosine: A rare amino acid found in elastin, formed by condensation of four molecules of lysine into a pyridinium ring.	3.43	1	1	aromatic amino acid
cytochrome c-t Cytochromes c: Cytochromes of the c type that are found in eukaryotic MITOCHONDRIA. They serve as redox intermediates that accept electrons from MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX III and transfer them to MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX IV.	2.43	2	0
fullerene c70 [no description available]	2.48	2	0	fullerene
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.	2.67	3	0	peptide hormone
conotoxin gv conotoxin GV: NMDA antagonist from Conus geographus	1.99	1	0
conantokin-t conantokin-T: from cone snail Conus tulipa; a 21-amino acid peptide which induces sleep-like symptoms in young mice; has N-methyl-D-aspartate antagonist activity; amino acid sequence given in first source	1.99	1	0
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	2.42	2	0	1,2-diacyl-sn-glycero-3-phosphocholine
atractyloside Atractyloside: A glycoside of a kaurene type diterpene that is found in some plants including Atractylis gummifera (ATRACTYLIS); COFFEE; XANTHIUM, and CALLILEPIS. Toxicity is due to inhibition of ADENINE NUCLEOTIDE TRANSLOCASE.	2.92	4	0
chlorophyll a Chlorophyll: Porphyrin derivatives containing magnesium that act to convert light energy in photosynthetic organisms.. chlorophyll : A family of magnesium porphyrins, defined by the presence of a fifth ring beyond the four pyrrole-like rings. The rings can have various side chains which usually include a long phytol chain.	2.02	1	0	chlorophyll; methyl ester	cofactor
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.	6.09	9	0
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.	2.72	3	0
chitosan [no description available]	7.07	1	0
sodium oxybate Sodium Oxybate: The sodium salt of 4-hydroxybutyric acid. It is used for both induction and maintenance of ANESTHESIA.	2.37	2	0
sodium hypochlorite Sodium Hypochlorite: It is used as an oxidizing and bleaching agent and as a disinfectant. (From Grant & Hackh's Chemical Dictionary, 5th ed). sodium hypochlorite : An inorganic sodium salt in which hypochlorite is the counterion. It is used as a bleaching and disinfecting agent and is commonly found in household bleach.	2.05	1	0	inorganic sodium salt	bleaching agent; disinfectant
4-hydroxymercuribenzoate [no description available]	1.97	1	0
sodium nitrite Sodium Nitrite: Nitrous acid sodium salt. Used in many industrial processes, in meat curing, coloring, and preserving, and as a reagent in ANALYTICAL CHEMISTRY TECHNIQUES. It is used therapeutically as an antidote in cyanide poisoning. The compound is toxic and mutagenic and will react in vivo with secondary or tertiary amines thereby producing highly carcinogenic nitrosamines.. sodium nitrite : An inorganic sodium salt having nitrite as the counterion. Used as a food preservative and antidote to cyanide poisoning.	1.99	1	0	inorganic sodium salt; nitrite salt	antidote to cyanide poisoning; antihypertensive agent; antimicrobial food preservative; food antioxidant; poison
sodium bromate sodium bromate : An inorganic sodium salt having bromate as the counterion.	3.45	7	0	bromate salt; inorganic sodium salt	nephrotoxin; oxidising agent
potassium bromate potassium bromate: used as bread improver	2.03	1	0	bromate salt; potassium salt	flour treatment agent
mersalyl Mersalyl: A toxic thiol mercury salt formerly used as a diuretic. It inhibits various biochemical functions, especially in mitochondria, and is used to study those functions.	2.64	3	0
chiniofon Hydroxyquinolines: The 8-hydroxy derivatives inhibit various enzymes and their halogenated derivatives, though neurotoxic, are used as topical anti-infective agents, among other uses.	1.92	1	0
srt1720 [no description available]	2.1	1	0
cardiovascular agents Cardiovascular Agents: Agents that affect the rate or intensity of cardiac contraction, blood vessel diameter, or blood volume.	1.94	1	0
nitrogenase Nitrogenase: An enzyme system that catalyzes the fixing of nitrogen in soil bacteria and blue-green algae (CYANOBACTERIA). EC 1.18.6.1.	2	1	0
gw 1000 nabiximols: a combination of the above cpds for treatment of multiple sclerosis pain	2.07	1	0
piperidines Piperidines: A family of hexahydropyridines.	2.44	2	0
bryostatin 1 bryostatin 1: a protein kinase C activator; macrocyclic lactone from marine Bryozoan Bugula neritina; RN given refers to (1S-(1R,3R,5Z,7S,8E,11R,12R(2E,4E),13E,15R,17S(S),21S,23S,25R))-isomer; structure given in first source; activates protein kinase c. bryostatin 1 : A member of the class of bryostatins that is (17E)-2-oxooxacyclohexacos-17-ene which is substituted by hydroxy groups at positions 4, 10, and 20; an acetoxy group at position 8; methyl groups at positions 9, 9, 18, and 19; 2-methoxy-2-oxoethylidene groups at positions 14 and 24; an (E,E)-octa-2,4-dienoyloxy group at position 21; and with oxygen bridges linking positions 6 to 10, 12 to 16, and 20 to 24. It is one of the most abundant member of the class of bryostatins.	2.04	1	0
3',5'-diiodothyronine 3',5'-diiodothyronine: RN given refers to (DL)-isomer	2.03	1	0	phenylalanine derivative
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	3.09	5	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.	2.1	1	0
minocycline Minocycline: A TETRACYCLINE analog, having a 7-dimethylamino and lacking the 5 methyl and hydroxyl groups, which is effective against tetracycline-resistant STAPHYLOCOCCUS infections.. minocycline : A tetracycline analogue having a dimethylamino group at position 7 and lacking the methyl and hydroxy groups at position 5.	2.71	3	0
salicylates Salicylates: The salts or esters of salicylic acids, or salicylate esters of an organic acid. Some of these have analgesic, antipyretic, and anti-inflammatory activities by inhibiting prostaglandin synthesis.. hydroxybenzoate : Any benzoate derivative carrying a single carboxylate group and at least one hydroxy substituent.. salicylates : Any salt or ester arising from reaction of the carboxy group of salicylic acid, or any ester resulting from the condensation of the phenolic hydroxy group of salicylic acid with an organic acid.. salicylate : A monohydroxybenzoate that is the conjugate base of salicylic acid.	2.43	2	0	monohydroxybenzoate	plant metabolite
dicumarol Dicumarol: An oral anticoagulant that interferes with the metabolism of vitamin K. It is also used in biochemical experiments as an inhibitor of reductases.	2.05	1	0	hydroxycoumarin	anticoagulant; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; Hsp90 inhibitor; vitamin K antagonist
warfarin Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.	2.45	2	0	benzenes; hydroxycoumarin; methyl ketone
antimycin [no description available]	3.61	9	0
teriflunomide [no description available]	2.05	1	0	(trifluoromethyl)benzenes; aromatic amide; enamide; enol; nitrile; secondary carboxamide	drug metabolite; EC 1.3.98.1 [dihydroorotate oxidase (fumarate)] inhibitor; hepatotoxic agent; non-steroidal anti-inflammatory drug; tyrosine kinase inhibitor
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.	2.01	1	0
microcystin microcystin: microcystins have the general structure cyclo(D-Ala-L-X-D-erythro--methylisoasp-L-Y-Adda-D-isoGlu-N-methyldehydroAla) where X and Y are variable L-amino acids;. microcystin : A family of cyclic heptapeptide hepatotoxins produced by a number of cyanobacteria, the most notable of which is Microcystis, from which the name of the family is derived. Microcystins consist of a heptapeptide macrocycle made up of five non-protein amino acids and two protein amino acids.	2.02	1	0	peptide
lead radioisotopes Lead Radioisotopes: Unstable isotopes of lead that decay or disintegrate emitting radiation. Pb atoms with atomic weights 194-203, 205, and 209-214 are radioactive lead isotopes.	2.03	1	0
maitotoxin [no description available]	2	1	0
phleomycin d1 phleomycin D1 : A glycopeptide originally isolated from the bacterium Streptomyces verticillus which contains a (4'R)-4',5'-dihydro-2,4'-bi-1,3-thiazole-2',4-diyl moiety with a a 4-guanidylbutylaminocarbonyl group attached to the 4-position of the terminal thiazole ring. Like all phleomycins, phleomycin D1 can form complexes with redox-active metals such as Co, Cu, and Fe.	2.17	1	0	bi-1,3-thiazole; chelate-forming peptide; disaccharide derivative; glycopeptide; guanidines	antibacterial agent; antifungal agent; antimicrobial agent; antineoplastic agent; bacterial metabolite
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).	3.36	7	0
morin-5'-sulfonic acid morin-5'-sulfonic acid: an antioxidant	2.1	1	0
benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone: an interleukin-1beta converting enzyme (ICE)-like protease inhibitor	2.4	2	0
nitrophenols Nitrophenols: PHENOLS carrying nitro group substituents.	2.88	4	0
cobamamide cobamamide : A member of the class of cobalamins that is vitamin B12 in which the cyano group is replaced by a 5'-deoxyadenos-5'-yl moiety. It is one of the two metabolically active form of vitamin B12.	2.01	1	0
carboxyatractyloside carboxyatractyloside: RN given refers to parent cpd; structure	2.42	2	0
nonactin nonactin: macrolide tetrolide antibiotic isolated from cycloheximide-producing species of Streptomyces; minor descriptor (75-86); on-line & INDEX MEDICUS search ANTIBIOTICS (75-86)	2.01	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.	2.63	3	0
cyclosporine Cyclosporine: A cyclic undecapeptide from an extract of soil fungi. It is a powerful immunosupressant with a specific action on T-lymphocytes. It is used for the prophylaxis of graft rejection in organ and tissue transplantation. (From Martindale, The Extra Pharmacopoeia, 30th ed).	1.99	1	0
ansamitocins ansamitocins: maytansinoid antibiotics produced by an actinomycete strain Norcardia sp. No. C-15003 (N-1); P-1 & P-2 identified with maytanacine & maytansinol propionate, respectively; structures for ansamitocins P-0, P-1, P-2, P-3, P-3', P-4 in second source	2.49	2	0
acyclovir Acyclovir: A GUANOSINE analog that acts as an antimetabolite. Viruses are especially susceptible. Used especially against herpes.. acyclovir : An oxopurine that is guanine substituted by a (2-hydroxyethoxy)methyl substituent at position 9. Used in the treatment of viral infections.	2.11	1	0	2-aminopurines; oxopurine	antimetabolite; antiviral drug
guanosine diphosphate Guanosine Diphosphate: A guanine nucleotide containing two phosphate groups esterified to the sugar moiety.	2.68	3	0	guanosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	Escherichia coli metabolite; mouse metabolite; uncoupling protein inhibitor
guanine [no description available]	7.01	1	0	2-aminopurines; oxopurine; purine nucleobase	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae 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	1	0	inosine phosphate; purine ribonucleoside 5'-monophosphate	Escherichia coli metabolite; human metabolite; mouse metabolite
inosine diphosphate Inosine Diphosphate: An inosine nucleotide containing a pyrophosphate group esterified to C5 of the sugar moiety.	1.97	1	0	inosine phosphate; purine ribonucleoside 5'-diphosphate	fundamental metabolite
folic acid folcysteine: used to promote fertility in chickens. vitamin B9 : Any B-vitamin that exhibits biological activity against vitamin B9 deficiency. Vitamin B9 refers to the many forms of folic acid and its derivatives, including tetrahydrofolic acid (the active form), methyltetrahydrofolate (the primary form found in blood), methenyltetrahydrofolate, folinic acid amongst others. They are present in abundance in green leafy vegetables, citrus fruits, and animal products. Lack of vitamin B9 leads to anemia, a condition in which the body cannot produce sufficient number of red blood cells. Symptoms of vitamin B9 deficiency include fatigue, muscle weakness, and pale skin.	1.93	1	0	folic acids; N-acyl-amino acid	human metabolite; mouse metabolite; nutrient
pheophytin a pheophytin a: structure given in first source; RN given refers to (3S-(3alpha(2E,7S,11S),4beta,21beta))-isomer	2.02	1	0
syringaldazine syringaldazine: used for detection of laccase in sporophores of wood rotting fungi; structure	2.02	1	0
sildenafil citrate Sildenafil Citrate: A PHOSPHODIESTERASE TYPE-5 INHIBITOR; VASODILATOR AGENT and UROLOGICAL AGENT that is used in the treatment of ERECTILE DYSFUNCTION and PRIMARY PULMONARY HYPERTENSION.. sildenafil citrate : The citrate salt of sildenafil.	2.49	2	0	citrate salt	EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor; vasodilator agent
remazol black b Remazol black B: RN given refers to the tetrasodium salt. remazole black-GR : A bis(azo) compound with two aryldiazenyl moieties placed at positions 2 and 7 of a multi-substituted naphthalene.	2.21	1	0
arsenazo iii Arsenazo III: Metallochrome indicator that changes color when complexed to the calcium ion under physiological conditions. It is used to measure local calcium ion concentrations in vivo.	1.97	1	0
antipyrylazo iii antipyrylazo III: a metallochromic indicator	1.96	1	0
carbidopa Carbidopa: An inhibitor of DOPA DECARBOXYLASE that prevents conversion of LEVODOPA to dopamine. It is used in PARKINSON DISEASE to reduce peripheral adverse effects of LEVODOPA. It has no anti-parkinson activity by itself.. carbidopa : The hydrate of 3-(3,4-dihydroxyphenyl)propanoic acid in which the hydrogens alpha- to the carboxyl group are substituted by hydrazinyl and methyl groups (S-configuration). Carbidopa is a dopa decarboxylase inhibitor, so prevents conversion of levodopa to dopamine. It has no antiparkinson activity by itself, but is used in the management of Parkinson's disease to reduce peripheral adverse effects of levodopa.	2	1	0
2',7'-bis-(2-carboxyethyl)-5(6)-carboxyfluorescein acetoxymethyl ester 2',7'-bis-(2-carboxyethyl)-5(6)-carboxyfluorescein acetoxymethyl ester: structure given in first source	1.98	1	0
2',7'-bis(carboxyethyl)-5(6)-carboxyfluorescein [no description available]	1.97	1	0
leptin Leptin: A 16-kDa peptide hormone secreted from WHITE ADIPOCYTES. Leptin serves as a feedback signal from fat cells to the CENTRAL NERVOUS SYSTEM in regulation of food intake, energy balance, and fat storage.	2.13	1	0

Condition	Relationship Strength	Studies	Trials
Experimental Leukemia [description not available]	2.37	2	0
Cochlear Hearing Loss [description not available]	2.15	1	0
Nodular Goiter [description not available]	2.15	1	0
Goiter, Nodular An enlarged THYROID GLAND containing multiple nodules (THYROID NODULE), usually resulting from recurrent thyroid HYPERPLASIA and involution over many years to produce the irregular enlargement. Multinodular goiters may be nontoxic or may induce THYROTOXICOSIS.	2.15	1	0
Hearing Loss, Sensorineural Hearing loss resulting from damage to the COCHLEA and the sensorineural elements which lie internally beyond the oval and round windows. These elements include the AUDITORY NERVE and its connections in the BRAINSTEM.	2.15	1	0
Inborn Errors of Metabolism [description not available]	4.05	14	0
Metabolism, Inborn Errors Errors in metabolic processes resulting from inborn genetic mutations that are inherited or acquired in utero.	4.05	14	0
Akinetic-Rigid Variant of Huntington Disease [description not available]	5.2	18	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)	5.2	18	0
Encephalopathy, Toxic [description not available]	2.77	3	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	5.79	33	0
Obesity A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).	2.63	2	0
Acne [description not available]	2.6	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.	2.6	1	0
Cardiovascular Stroke [description not available]	2.94	3	0
Myocardial Infarction NECROSIS of the MYOCARDIUM caused by an obstruction of the blood supply to the heart (CORONARY CIRCULATION).	2.94	3	0
ST Elevated Myocardial Infarction [description not available]	2.25	1	0
ST Elevation Myocardial Infarction A clinical syndrome defined by MYOCARDIAL ISCHEMIA symptoms; persistent elevation in the ST segments of the ELECTROCARDIOGRAM; and release of BIOMARKERS of myocardial NECROSIS (e.g., elevated TROPONIN levels). ST segment elevation in the ECG is often used in determining the treatment protocol (see also NON-ST ELEVATION MYOCARDIAL INFARCTION).	2.25	1	0
Acute Ischemic Stroke [description not available]	2.31	1	0
Ischemic Stroke Stroke due to BRAIN ISCHEMIA resulting in interruption or reduction of blood flow to a part of the brain. When obstruction is due to a BLOOD CLOT formed within in a cerebral blood vessel it is a thrombotic stroke. When obstruction is formed elsewhere and moved to block a cerebral blood vessel (see CEREBRAL EMBOLISM) it is referred to as embolic stroke. Wake-up stroke refers to ischemic stroke occurring during sleep while cryptogenic stroke refers to ischemic stroke of unknown origin.	2.31	1	0
Cardiomyopathy, Congestive [description not available]	2.25	1	0
Cardiomyopathy, Dilated A form of CARDIAC MUSCLE disease that is characterized by ventricular dilation, VENTRICULAR DYSFUNCTION, and HEART FAILURE. Risk factors include SMOKING; ALCOHOL DRINKING; HYPERTENSION; INFECTION; PREGNANCY; and mutations in the LMNA gene encoding LAMIN TYPE A, a NUCLEAR LAMINA protein.	2.25	1	0
Injury, Myocardial Reperfusion [description not available]	2.83	3	0
Blood Pressure, High [description not available]	2.25	1	0
Hypertension Persistently high systemic arterial BLOOD PRESSURE. Based on multiple readings (BLOOD PRESSURE DETERMINATION), hypertension is currently defined as when SYSTOLIC PRESSURE is consistently greater than 140 mm Hg or when DIASTOLIC PRESSURE is consistently 90 mm Hg or more.	2.25	1	0
Amino Acid Metabolism Disorders, Inborn [description not available]	4.22	6	0
Hepatocellular Carcinoma [description not available]	2.31	1	0
Cancer of Liver [description not available]	2.31	1	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.	2.31	1	0
Liver Neoplasms Tumors or cancer of the LIVER.	2.31	1	0
Adjuvant Arthritis [description not available]	2.31	1	0
Innate Inflammatory Response [description not available]	2.54	2	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.	2.54	2	0
Carbon Monoxide Poisoning Toxic asphyxiation due to the displacement of oxygen from oxyhemoglobin by carbon monoxide.	2.31	1	0
Cardiomyopathies, Primary [description not available]	2.75	3	0
Cardiomyopathies A group of diseases in which the dominant feature is the involvement of the CARDIAC MUSCLE itself. Cardiomyopathies are classified according to their predominant pathophysiological features (DILATED CARDIOMYOPATHY; HYPERTROPHIC CARDIOMYOPATHY; RESTRICTIVE CARDIOMYOPATHY) or their etiological/pathological factors (CARDIOMYOPATHY, ALCOHOLIC; ENDOCARDIAL FIBROELASTOSIS).	2.75	3	0
Infections, Pseudomonas [description not available]	2.15	1	0
Pseudomonas Infections Infections with bacteria of the genus PSEUDOMONAS.	2.15	1	0
Benign Neoplasms [description not available]	3.05	5	0
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	3.05	5	0
BCKD Deficiency [description not available]	3.38	2	0
Maple Syrup Urine Disease An autosomal recessive inherited disorder with multiple forms of phenotypic expression, caused by a defect in the oxidative decarboxylation of branched-chain amino acids (AMINO ACIDS, BRANCHED-CHAIN). These metabolites accumulate in body fluids and render a maple syrup odor. The disease is divided into classic, intermediate, intermittent, and thiamine responsive subtypes. The classic form presents in the first week of life with ketoacidosis, hypoglycemia, emesis, neonatal seizures, and hypertonia. The intermediate and intermittent forms present in childhood or later with acute episodes of ataxia and vomiting. (From Adams et al., Principles of Neurology, 6th ed, p936)	3.38	2	0
Anoxia, Brain [description not available]	3.09	5	0
Cognition Disorders Disorders characterized by disturbances in mental processes related to learning, thinking, reasoning, and judgment.	2.08	1	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.	3.81	11	0
Apoplexy [description not available]	2.1	1	0
Cerebral Ischemia [description not available]	3.39	7	0
Injury, Ischemia-Reperfusion [description not available]	2.44	2	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.	3.39	7	0
Reperfusion Injury Adverse functional, metabolic, or structural changes in tissues that result from the restoration of blood flow to the tissue (REPERFUSION) following ISCHEMIA.	2.44	2	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)	2.1	1	0
Breast Cancer [description not available]	2.77	3	0
Breast Neoplasms Tumors or cancer of the human BREAST.	2.77	3	0
Metabolic Acidosis [description not available]	3.25	6	0
Acidosis A pathologic condition of acid accumulation or depletion of base in the body. The two main types are RESPIRATORY ACIDOSIS and metabolic acidosis, due to metabolic acid build up.	3.25	6	0
Acute Brain Injuries [description not available]	2.43	2	0
Brain Injuries Acute and chronic (see also BRAIN INJURIES, CHRONIC) injuries to the brain, including the cerebral hemispheres, CEREBELLUM, and BRAIN STEM. Clinical manifestations depend on the nature of injury. Diffuse trauma to the brain is frequently associated with DIFFUSE AXONAL INJURY or COMA, POST-TRAUMATIC. Localized injuries may be associated with NEUROBEHAVIORAL MANIFESTATIONS; HEMIPARESIS, or other focal neurologic deficits.	2.43	2	0
Hyperplasia An increase in the number of cells in a tissue or organ without tumor formation. It differs from HYPERTROPHY, which is an increase in bulk without an increase in the number of cells.	2.13	1	0
Hypertrophy General increase in bulk of a part or organ due to CELL ENLARGEMENT and accumulation of FLUIDS AND SECRETIONS, not due to tumor formation, nor to an increase in the number of cells (HYPERPLASIA).	2.13	1	0
Alloxan Diabetes [description not available]	2.45	2	0
Hyperglycemia, Postprandial Abnormally high BLOOD GLUCOSE level after a meal.	2.4	2	0
Hyperglycemia Abnormally high BLOOD GLUCOSE level.	2.4	2	0
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	3.26	6	0
Impaired Glucose Tolerance [description not available]	2.05	1	0
Glucose Intolerance A pathological state in which BLOOD GLUCOSE level is less than approximately 140 mg/100 ml of PLASMA at fasting, and above approximately 200 mg/100 ml plasma at 30-, 60-, or 90-minute during a GLUCOSE TOLERANCE TEST. This condition is seen frequently in DIABETES MELLITUS, but also occurs with other diseases and MALNUTRITION.	2.05	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.	3.43	1	1
Anterior Horn Cell Disease [description not available]	2.05	1	0
Motor Neuron Disease Diseases characterized by a selective degeneration of the motor neurons of the spinal cord, brainstem, or motor cortex. Clinical subtypes are distinguished by the major site of degeneration. In AMYOTROPHIC LATERAL SCLEROSIS there is involvement of upper, lower, and brainstem motor neurons. In progressive muscular atrophy and related syndromes (see MUSCULAR ATROPHY, SPINAL) the motor neurons in the spinal cord are primarily affected. With progressive bulbar palsy (BULBAR PALSY, PROGRESSIVE), the initial degeneration occurs in the brainstem. In primary lateral sclerosis, the cortical neurons are affected in isolation. (Adams et al., Principles of Neurology, 6th ed, p1089)	2.05	1	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	2.46	2	0
Insulin Sensitivity [description not available]	2.05	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.	2.05	1	0
Absence Seizure [description not available]	2.41	2	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.	2.41	2	0
Heart Disease, Ischemic [description not available]	2.42	2	0
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).	2.42	2	0
Cardiac Cancer [description not available]	2.06	1	0
Muscle Tissue Neoplasms [description not available]	2.06	1	0
Metastase [description not available]	2.06	1	0
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	2.06	1	0
Depression, Involutional Form of depression in those MIDDLE AGE with feelings of ANXIETY.	2.08	1	0
Depressive Disorder, Major Disorder in which five (or more) of the following symptoms have been present during the same 2-week period and represent a change from previous functioning; at least one of the symptoms is either (1) depressed mood or (2) loss of interest or pleasure. Symptoms include: depressed mood most of the day, nearly every daily; markedly diminished interest or pleasure in activities most of the day, nearly every day; significant weight loss when not dieting or weight gain; Insomnia or hypersomnia nearly every day; psychomotor agitation or retardation nearly every day; fatigue or loss of energy nearly every day; feelings of worthlessness or excessive or inappropriate guilt; diminished ability to think or concentrate, or indecisiveness, nearly every day; or recurrent thoughts of death, recurrent suicidal ideation without a specific plan, or a suicide attempt. (DSM-5)	2.08	1	0
Brain Swelling [description not available]	2.91	4	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)	2.91	4	0
Anochlesia [description not available]	2.01	1	0
Catatonic Rigidity [description not available]	2.01	1	0
Atherosclerotic Parkinsonism [description not available]	2.41	2	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)	2.01	1	0
Parkinson Disease, Secondary Conditions which feature clinical manifestations resembling primary Parkinson disease that are caused by a known or suspected condition. Examples include parkinsonism caused by vascular injury, drugs, trauma, toxin exposure, neoplasms, infections and degenerative or hereditary conditions. Clinical features may include bradykinesia, rigidity, parkinsonian gait, and masked facies. In general, tremor is less prominent in secondary parkinsonism than in the primary form. (From Joynt, Clinical Neurology, 1998, Ch38, pp39-42)	2.41	2	0
Coma A profound state of unconsciousness associated with depressed cerebral activity from which the individual cannot be aroused. Coma generally occurs when there is dysfunction or injury involving both cerebral hemispheres or the brain stem RETICULAR FORMATION.	2.01	1	0
Idiopathic Parkinson Disease [description not available]	2.7	3	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)	2.7	3	0
Electron Transport Chain Deficiencies, Mitochondrial [description not available]	2.72	3	0
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	3.58	9	0
Mitochondrial Diseases Diseases caused by abnormal function of the MITOCHONDRIA. They may be caused by mutations, acquired or inherited, in mitochondrial DNA or in nuclear genes that code for mitochondrial components. They may also be the result of acquired mitochondria dysfunction due to adverse effects of drugs, infections, or other environmental causes.	2.72	3	0
Infections, Salmonella [description not available]	1.93	1	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.	6.93	1	0
Depression Depressive states usually of moderate intensity in contrast with MAJOR DEPRESSIVE DISORDER present in neurotic and psychotic disorders.	1.93	1	0
Anaphylactic Reaction [description not available]	1.93	1	0
Allergic Reaction [description not available]	1.93	1	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.	1.93	1	0
Hypersensitivity Altered reactivity to an antigen, which can result in pathologic reactions upon subsequent exposure to that particular antigen.	1.93	1	0
Anoxemia [description not available]	3.36	7	0
Hypoxia Sub-optimal OXYGEN levels in the ambient air of living organisms.	3.36	7	0
Deficiency, Vitamin B 12 [description not available]	1.93	1	0
Vitamin B 12 Deficiency A nutritional condition produced by a deficiency of VITAMIN B 12 in the diet, characterized by megaloblastic anemia. Since vitamin B 12 is not present in plants, humans have obtained their supply from animal products, from multivitamin supplements in the form of pills, and as additives to food preparations. A wide variety of neuropsychiatric abnormalities is also seen in vitamin B 12 deficiency and appears to be due to an undefined defect involving myelin synthesis. (From Cecil Textbook of Medicine, 19th ed, p848)	1.93	1	0
Addison's Anemia [description not available]	1.93	1	0
Brain Vascular Disorders [description not available]	1.93	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.	1.93	1	0
Curling Ulcer Acute stress DUODENAL ULCER, usually observed in patients with extensive third-degree burns.	1.93	1	0
Duodenal Ulcer A PEPTIC ULCER located in the DUODENUM.	1.93	1	0
Extravascular Hemolysis [description not available]	1.94	1	0
Hemolysis The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.	1.94	1	0
Deficiency Diseases A condition produced by dietary or metabolic deficiency. The term includes all diseases caused by an insufficient supply of essential nutrients, i.e., protein (or amino acids), vitamins, and minerals. It also includes an inadequacy of calories. (From Dorland, 27th ed; Stedman, 25th ed)	1.94	1	0
Deficiency, Vitamin B [description not available]	1.94	1	0
Vitamin B Deficiency A condition due to deficiency in any member of the VITAMIN B COMPLEX. These B vitamins are water-soluble and must be obtained from the diet because they are easily lost in the urine. Unlike the lipid-soluble vitamins, they cannot be stored in the body fat.	1.94	1	0
Ischemia A hypoperfusion of the BLOOD through an organ or tissue caused by a PATHOLOGIC CONSTRICTION or obstruction of its BLOOD VESSELS, or an absence of BLOOD CIRCULATION.	2.01	1	0
Autosomal Dominant Juvenile Parkinson Disease [description not available]	2.71	3	0
Parkinsonian Disorders A group of disorders which feature impaired motor control characterized by bradykinesia, MUSCLE RIGIDITY; TREMOR; and postural instability. Parkinsonian diseases are generally divided into primary parkinsonism (see PARKINSON DISEASE), secondary parkinsonism (see PARKINSON DISEASE, SECONDARY) and inherited forms. These conditions are associated with dysfunction of dopaminergic or closely related motor integration neuronal pathways in the BASAL GANGLIA.	2.71	3	0
Brain Disorders [description not available]	3.1	5	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.	3.1	5	0
Genetic Predisposition [description not available]	2.42	2	0
Degenerative Diseases, Central Nervous System [description not available]	2.92	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.	2.92	4	0
HIV Coinfection [description not available]	2.02	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.	2.02	1	0
HIV Infections Includes the spectrum of human immunodeficiency virus infections that range from asymptomatic seropositivity, thru AIDS-related complex (ARC), to acquired immunodeficiency syndrome (AIDS).	2.02	1	0
Aura [description not available]	2.02	1	0
Acute Disease Disease having a short and relatively severe course.	2.42	2	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)	2.02	1	0
Muscle Spasm [description not available]	1.92	1	0
Spasm An involuntary contraction of a muscle or group of muscles. Spasms may involve SKELETAL MUSCLE or SMOOTH MUSCLE.	6.92	1	0
Pyrexia [description not available]	2.02	1	0
Fever An abnormal elevation of body temperature, usually as a result of a pathologic process.	2.02	1	0
Weight Gain Increase in BODY WEIGHT over existing weight.	2.02	1	0
Anasarca [description not available]	2.02	1	0
MPTP Neurotoxicity Syndrome [description not available]	2.92	4	0
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	2.02	1	0
Autolysis The spontaneous disintegration of tissues or cells by the action of their own autogenous enzymes.	2.02	1	0
ALS - Amyotrophic Lateral Sclerosis [description not available]	2.42	2	0
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)	2.42	2	0
Disease Exacerbation [description not available]	2.03	1	0
Allergic Encephalomyelitis [description not available]	2.03	1	0
Dyskinesia Syndromes [description not available]	2.41	2	0
MS (Multiple Sclerosis) [description not available]	2.03	1	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.	2.41	2	0
Multiple Sclerosis An autoimmune disorder mainly affecting young adults and characterized by destruction of myelin in the central nervous system. Pathologic findings include multiple sharply demarcated areas of demyelination throughout the white matter of the central nervous system. Clinical manifestations include visual loss, extra-ocular movement disorders, paresthesias, loss of sensation, weakness, dysarthria, spasticity, ataxia, and bladder dysfunction. The usual pattern is one of recurrent attacks followed by partial recovery (see MULTIPLE SCLEROSIS, RELAPSING-REMITTING), but acute fulminating and chronic progressive forms (see MULTIPLE SCLEROSIS, CHRONIC PROGRESSIVE) also occur. (Adams et al., Principles of Neurology, 6th ed, p903)	2.03	1	0
Amphetamine Abuse [description not available]	2.03	1	0
Amphetamine-Related Disorders Disorders related or resulting from use of amphetamines.	2.03	1	0
Glial Cell Tumors [description not available]	2.02	1	0
Experimental Neoplasms [description not available]	2.02	1	0
Experimental Mammary Neoplasms [description not available]	2.68	3	0
Glioma Benign and malignant central nervous system neoplasms derived from glial cells (i.e., astrocytes, oligodendrocytes, and ependymocytes). Astrocytes may give rise to astrocytomas (ASTROCYTOMA) or glioblastoma multiforme (see GLIOBLASTOMA). Oligodendrocytes give rise to oligodendrogliomas (OLIGODENDROGLIOMA) and ependymocytes may undergo transformation to become EPENDYMOMA; CHOROID PLEXUS NEOPLASMS; or colloid cysts of the third ventricle. (From Escourolle et al., Manual of Basic Neuropathology, 2nd ed, p21)	2.02	1	0
Cerebral Infarction, Middle Cerebral Artery [description not available]	2.03	1	0
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.	2.03	1	0
Disomy, Uniparental [description not available]	2.03	1	0
Central Hypothyroidism [description not available]	2.4	2	0
Hypothyroidism A syndrome that results from abnormally low secretion of THYROID HORMONES from the THYROID GLAND, leading to a decrease in BASAL METABOLIC RATE. In its most severe form, there is accumulation of MUCOPOLYSACCHARIDES in the SKIN and EDEMA, known as MYXEDEMA. It may be primary or secondary due to other pituitary disease, or hypothalamic dysfunction.	2.4	2	0
Acquired Metabolic Diseases, Brain [description not available]	2.04	1	0
Wallerian Degeneration Degeneration of distal aspects of a nerve axon following injury to the cell body or proximal portion of the axon. The process is characterized by fragmentation of the axon and its MYELIN SHEATH.	2.04	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.	2.38	2	0
Cancer of Lung [description not available]	2.37	2	0
Lung Neoplasms Tumors or cancer of the LUNG.	2.37	2	0
Carcinoma, Ehrlich Tumor A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.	2.38	2	0
Hyperthyroid [description not available]	2.38	2	0
Hyperthyroidism Hypersecretion of THYROID HORMONES from the THYROID GLAND. Elevated levels of thyroid hormones increase BASAL METABOLIC RATE.	2.38	2	0
Decreased Muscle Tone [description not available]	1.98	1	0
Cafe-au-Lait Spots with Pulmonic Stenosis [description not available]	1.98	1	0
Neurofibromatosis 1 An autosomal dominant inherited disorder (with a high frequency of spontaneous mutations) that features developmental changes in the nervous system, muscles, bones, and skin, most notably in tissue derived from the embryonic NEURAL CREST. Multiple hyperpigmented skin lesions and subcutaneous tumors are the hallmark of this disease. Peripheral and central nervous system neoplasms occur frequently, especially OPTIC NERVE GLIOMA and NEUROFIBROSARCOMA. NF1 is caused by mutations which inactivate the NF1 gene (GENES, NEUROFIBROMATOSIS 1) on chromosome 17q. The incidence of learning disabilities is also elevated in this condition. (From Adams et al., Principles of Neurology, 6th ed, pp1014-18) There is overlap of clinical features with NOONAN SYNDROME in a syndrome called neurofibromatosis-Noonan syndrome. Both the PTPN11 and NF1 gene products are involved in the SIGNAL TRANSDUCTION pathway of Ras (RAS PROTEINS).	1.98	1	0
Nervous System Disorders [description not available]	2.39	2	0
Nervous System Diseases Diseases of the central and peripheral nervous system. This includes disorders of the brain, spinal cord, cranial nerves, peripheral nerves, nerve roots, autonomic nervous system, neuromuscular junction, and muscle.	2.39	2	0
Cerebro-Hepato-Renal Syndrome [description not available]	1.98	1	0
Zellweger Syndrome An autosomal recessive disorder due to defects in PEROXISOME biogenesis which involves more than 13 genes encoding peroxin proteins of the peroxisomal membrane and matrix. Zellweger syndrome is typically seen in the neonatal period with features such as dysmorphic skull; MUSCLE HYPOTONIA; SENSORINEURAL HEARING LOSS; visual compromise; SEIZURES; progressive degeneration of the KIDNEYS and the LIVER. Zellweger-like syndrome refers to phenotypes resembling the neonatal Zellweger syndrome but seen in children or adults with apparently intact peroxisome biogenesis.	1.98	1	0
Bladder Cancer [description not available]	1.98	1	0
EHS Tumor [description not available]	1.98	1	0
Urinary Bladder Neoplasms Tumors or cancer of the URINARY BLADDER.	1.98	1	0
Encephalomyopathies, Mitochondrial [description not available]	1.98	1	0
Canine Diseases [description not available]	2.4	2	0
Encephalomyelitis, Inflammatory [description not available]	1.99	1	0
Aqueductal Stenosis [description not available]	1.99	1	0
Encephalomyelitis A general term indicating inflammation of the BRAIN and SPINAL CORD, often used to indicate an infectious process, but also applicable to a variety of autoimmune and toxic-metabolic conditions. There is significant overlap regarding the usage of this term and ENCEPHALITIS in the literature.	1.99	1	0
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	1.99	1	0
Cardiomyopathy, Hypertrophic Obstructive [description not available]	2	1	0
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).	2	1	0
Convulsions, Grand Mal [description not available]	2	1	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	1	0
Anoxia-Ischemia, Brain [description not available]	2	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	1	0
Leukemia, Lymphocytic, T Cell [description not available]	2	1	0
Leukemia, T-Cell A malignant disease of the T-LYMPHOCYTES in the bone marrow, thymus, and/or blood.	2	1	0
Arthus Phenomenon [description not available]	2	1	0
Adenocarcinoma, Basal Cell [description not available]	1.98	1	0
Carcinoma, Non-Small Cell Lung [description not available]	1.98	1	0
Cancer of Colon [description not available]	1.98	1	0
Leukemia L 1210 [description not available]	1.98	1	0
B16 Melanoma [description not available]	1.98	1	0
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	1.98	1	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.	1.98	1	0
Colonic Neoplasms Tumors or cancer of the COLON.	1.98	1	0
Alkalosis A pathological condition that removes acid or adds base to the body fluids.	2.37	2	0
Ureteral Obstruction Blockage in any part of the URETER causing obstruction of urine flow from the kidney to the URINARY BLADDER. The obstruction may be congenital, acquired, unilateral, bilateral, complete, partial, acute, or chronic. Depending on the degree and duration of the obstruction, clinical features vary greatly such as HYDRONEPHROSIS and obstructive nephropathy.	1.97	1	0
Contact Dermatitis [description not available]	1.97	1	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.	1.97	1	0
Experimental Hepatoma [description not available]	1.97	1	0

malonic acid

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