acetyl coenzyme a profile

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

ID Source	ID
PubMed CID	444493
CHEMBL ID	1230809
CHEBI ID	15351
SCHEMBL ID	6086
MeSH ID	M0000158

Synonym
s-[2-[3-[[(2r)-4-[[[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] ethanethioate
CHEMBL1230809 ,
gtpl3038
acetylcoa
accoa
CHEBI:15351 ,
3'-phosphoadenosine 5'-(3-{(3r)-4-[(3-{[2-(acetylsulfanyl)ethyl]amino}-3-oxopropyl)amino]-3-hydroxy-2,2-dimethyl-4-oxobutyl} dihydrogen diphosphate)
s-acetyl-coa
s-acetyl-coenzyme a
ACO ,
9h-purin-6-amine,9-[5-o-[[[[[(3r)-4-[[3-[[2-(acetylthio)ethyl]amino]-3-oxopropyl]amino]-3-hydroxy-2,2-dimethyl-4-oxobutyl]oxy]hydroxyphosphinyl]oxy]hydroxyphosphinyl]-3-o-phosphono-beta-d-ribofuranosy
s-acetylcoenzyme a
l]-
coenzyme a, s-acetate
acetyl coenzyme *a
ACETYL-COA ,
C00024
ac-coa
MOLI001840
ac-s-coa
acetyl coenzyme a
acetyl-s-coa
72-89-9
acetyl coa
s-acetyl coenzyme a
unii-76q83ylo3o
76q83ylo3o ,
einecs 200-790-9
AKOS025311419
ZSLZBFCDCINBPY-ZSJPKINUSA-N
s-acetyl coa
SCHEMBL6086
LMFA07050281
bdbm213238
acetyl-s-coenzyme a
ac-s-coenzyme a
ac-coenzyme a
s-acetate coa
s-acetate coenzyme a
66874-07-5
s-{(9r,13s,15s)-17-[(2r,3s,4r,5r)-5-(6-amino-9h-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]-9,13,15-trihydroxy-10,10-dimethyl-13,15-dioxido-4,8-dioxo-12,14,16-trioxa-3,7-diaza-13,15-diphosphaheptadec-1-yl} ethanethioate (non-preferred name
acetyl coenzyme a trilithium salt trihydrate
DTXSID30992686
Q715317
bdbm50541870
11c-acetylcoenzyme-a; (acyl-coa); [m+h]+;
12-hydroxy taurolithocholic acid sulfate disodium salt
CS-0081944
HY-114293

Excerpt	Reference	Relevance
" While some degrees of inhibition of metabolic activity were evident, these compounds were not responsible for the toxic effects produced by (R)-3-chlorolactate."	( The renal toxicity of (R)-3-chlorolactate in the rat. Jones, AR; Porter, KE, 1987)	0.27

Excerpt	Reference	Relevance
" DMPP was poorly absorbed in the fasting subjects."	( Influence of high-fat meal on the absorption of a silicon-containing amide, an inhibitor of acyl-CoA: cholesterol acyltransferase, in man. Jaffe, JM; Tse, FL, )	0.13
" Although a considerable amount of work has addressed the environmental factors that control methylmercury formation and the conditions that control bioavailability of inorganic mercury to SRB, little work has been undertaken analyzing the biochemical mechanism of methylmercury production."	( Mercury methylation independent of the acetyl-coenzyme A pathway in sulfate-reducing bacteria. Benoit, JM; Ekstrom, EB; Morel, FM, 2003)	0.32
" Taking into account the discovery of new functions of CoA (redox-dependent processes of CoAlation of proteins, possible association of oxidative stress and deficiency of Pan (CoA) in neurodegenerative pathology), it seems promising to study bioavailability and biotransformation of Pan derivatives, in particular of D-panthenol, 4'-phospho-pantetheine, its acylated derivatives, and compositions with redox pharmacological compounds, are promising for their potential use as etiopathogenetic agents."	( Brain CoA and Acetyl CoA Metabolism in Mechanisms of Neurodegeneration. Kanunnikova, NP; Moiseenok, AG, 2023)	0.91

Excerpt	Relevance	Reference
" Because it has a low therapeutic index, monitoring of serum levels may help to insure adequacy of dosage and avoid toxicity."	( Radioimmunoassay, acetylating radio-enzymatic assay, and microbioassay of gentamicin: a comparative study. Hewitt, WL; Stevens, P; Young, LS, 1975)	0.25
" In dose-response studies in which the concentrations of AF, AcCoA or S9 protein were varied, higher numbers of revertants were consistently generated with hepatic S9 derived from the slow acetylator compared to the rapid acetylator hamsters."	( Relationship of Syrian inbred hamster acetylator genotype to the mutagenic activation of 2-aminofluorene. Andrews, AF; Ferguson, RJ; Heflich, RH; Hein, DW; Kirlin, WG; Minor, TY; Ogolla, F; Trinidad, A; Yerokun, T, 1990)	0.28
" A similar gene dose-response relationship was exhibited by the polymorphic N-acetyltransferase enzyme toward isoniazid and procainamide."	( Biochemical investigation of the basis for the genetic N-acetylation polymorphism in the inbred hamster. Ferguson, RJ; Hein, DW; Kirlin, WG; Weber, WW, 1985)	0.27
" Further work is needed to define the mechanism by which exogenous carnitine improves exercise performance in order to better define potential patient populations for therapy and to facilitate optimal dosing regimens."	( Carnitine metabolism during exercise. Brass, EP; Hiatt, WR, 1994)	0.29
" We have used two-dimensional differential in-gel electrophoresis and mass spectrometry to identify a proteomic signature associated with hepatocellular steatosis in rats after dosing with a compound in preclinical development."	( A proteomic investigation of drug-induced steatosis in rat liver. Cristea, I; Gaskell, SJ; Guest, PC; Knowles, MR; Lawrence, J; Meneses-Lorente, G; Mortishire-Smith, R; Muniappa, N; Salim, K; Skynner, HA; Watt, A, 2004)	0.32
" These lesions usually affect one allele, suggesting that reduction in HAT dosage is important for lymphomagenesis."	( Inactivating mutations of acetyltransferase genes in B-cell lymphoma. Brindle, PK; Chadburn, A; Chiarenza, A; Dalla-Favera, R; Dominguez-Sola, D; Fabbri, G; Gaidano, G; Grunn, A; Kasper, LH; Lerach, S; Ma, J; Mullighan, CG; Murty, VV; Pasqualucci, L; Rabadan, R; Rossi, D; Tang, H; Trifonov, V, 2011)	0.37
" The results of this study demonstrate the ability of the organism to transform high concentrations of the oxidized form of CoQ(10) into the effective antioxidant (reduced) form and justify prospects of the development of parenteral dosage forms of CoQ(10) for the use in the treatment of acute pathological conditions."	( [Hplc estimation of coenzyme Q(10) redox status in plasma after intravenous coenzyme Q(10) administration]. Gorodetskaya, EA; Kalenikova, EI; Kharitonova, EV; Medvedev, OS; Tokareva, OG, )	0.13
"9 nmol/g), which persisted at 60 min after dosing (21."	( Increased anaplerosis of the tricarboxylic acid cycle decreased meal size and energy intake of cows in the postpartum period. Allen, MS; Gualdrón-Duarte, LB, 2017)	0.46

Role	Description
effector	A small molecule which increases (activator) or decreases (inhibitor) the activity of an (allosteric) enzyme by binding to the enzyme at the regulatory site (which is different from the substrate-binding catalytic site).
coenzyme	A low-molecular-weight, non-protein organic compound participating in enzymatic reactions as dissociable acceptor or donor of chemical groups or electrons.
acyl donor	Any donor that can transfer acyl groups between molecular entities.
fundamental metabolite	Any metabolite produced by all living cells.
[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
acyl-CoA	A thioester that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of any carboxylic 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
Amino acid synthesis and interconversion (transamination)	23	43
Citric Acid Cycle	21	27
beta-Alanine Metabolism	9	27
Glycine and Serine Metabolism	24	52
Glutamate Metabolism	22	44
Ketone Body Metabolism	4	13
Valine, Leucine, and Isoleucine Degradation	28	52
Oxidation of Branched-Chain Fatty Acids	11	22
Lysine Degradation	13	24
Fatty Acid Metabolism	14	41
Tryptophan Metabolism	18	55
Pyruvate Metabolism	21	39
Propanoate Metabolism	18	37
Amino Sugar Metabolism	17	31
Butyrate Metabolism	7	18
Caffeine Metabolism	8	21
Ethanol Degradation	7	16
Fatty Acid Elongation in Mitochondria	7	34
Steroid Biosynthesis	21	42
Phytanic Acid Peroxisomal Oxidation	6	20
beta-Ketothiolase Deficiency	28	52
2-Methyl-3-hydroxybutyryl-CoA Dehydrogenase Deficiency	28	52
Propionic Acidemia	28	52
3-Hydroxy-3-methylglutaryl-CoA Lyase Deficiency	28	52
Maple Syrup Urine Disease	28	52
3-Methylcrotonyl-CoA Carboxylase Deficiency Type I	28	52
3-Methylglutaconic Aciduria Type I	28	52
3-Methylglutaconic Aciduria Type III	28	52
Methylmalonate Semialdehyde Dehydrogenase Deficiency	28	52
Methylmalonic Aciduria	28	52
4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency	22	44
Homocarnosinosis	22	44
Hyperinsulinism-Hyperammonemia Syndrome	22	44
Isovaleric Aciduria	28	52
Smith-Lemli-Opitz Syndrome (SLOS)	21	42
CHILD Syndrome	21	42
Desmosterolosis	21	42
Chondrodysplasia Punctata II, X-Linked Dominant (CDPX2)	21	42
Lysosomal Acid Lipase Deficiency (Wolman Disease)	21	42
Ethylmalonic Encephalopathy	14	41
Glutaric Aciduria Type I	14	41
Short-Chain Acyl-CoA Dehydrogenase Deficiency (SCAD Deficiency)	14	41
GABA-Transaminase Deficiency	9	27
Saccharopinuria/Hyperlysinemia II	13	24
Leigh Syndrome	21	39
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)	21	39
Pyruvate Dehydrogenase Complex Deficiency	21	39
Refsum Disease	6	20
Sialuria or French Type Sialuria	17	31
Salla Disease/Infantile Sialic Acid Storage Disease	17	31
Ibandronate Action Pathway	21	43
Simvastatin Action Pathway	21	43
Pravastatin Action Pathway	21	43
Rosuvastatin Action Pathway	21	43
Alendronate Action Pathway	21	43
Transfer of Acetyl Groups into Mitochondria	9	19
Beta Oxidation of Very Long Chain Fatty Acids	10	13
Retinol Metabolism	37	30
Fatty Acid Biosynthesis	2	33
Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids	8	18
Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty Acids	8	23
Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty Acids	10	25
Dimethylglycine Dehydrogenase Deficiency	24	52
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)	24	52
Sarcosinemia	24	52
Malonic Aciduria	18	37
Methylmalonic Aciduria Due to Cobalamin-Related Disorders	18	37
Non-Ketotic Hyperglycinemia	24	52
Vitamin A Deficiency	37	30
2-Hydroxyglutric Aciduria (D and L Form)	22	44
3-Methylglutaconic Aciduria Type IV	28	52
Tay-Sachs Disease	17	31
Hypercholesterolemia	21	42
Lovastatin Action Pathway	21	43
Zoledronate Action Pathway	21	43
Cerivastatin Action Pathway	21	43
Risedronate Action Pathway	21	43
Pamidronate Action Pathway	21	43
Fluvastatin Action Pathway	21	43
Atorvastatin Action Pathway	21	43
Disulfiram Action Pathway	23	66
Hyperglycinemia, Non-Ketotic	24	52
Ureidopropionase Deficiency	9	27
Carnosinuria, Carnosinemia	9	27
Malonyl-CoA Decarboxylase Deficiency	18	37
Cholesteryl Ester Storage Disease	21	42
Hyper-IgD Syndrome	21	42
Mevalonic Aciduria	21	42
Wolman Disease	21	42
Adrenoleukodystrophy, X-Linked	10	13
Carnitine-Acylcarnitine Translocase Deficiency	10	13
3-Hydroxyisobutyric Acid Dehydrogenase Deficiency	28	52
3-Hydroxyisobutyric Aciduria	28	52
Isobutyryl-CoA Dehydrogenase Deficiency	28	52
Isovaleric Acidemia	28	52
Hyperlysinemia I, Familial	13	24
Hyperlysinemia II or Saccharopinuria	13	24
G(M2)-Gangliosidosis: Variant B, Tay-Sachs Disease	17	31
Carnitine Palmitoyl Transferase Deficiency I	14	41
Long Chain Acyl-CoA Dehydrogenase Deficiency (LCAD)	14	41
Very-Long-Chain Acyl-CoA Dehydrogenase Deficiency (VLCAD)	14	41
Carnitine Palmitoyl Transferase Deficiency II	14	41
Medium Chain Acyl-CoA Dehydrogenase Deficiency (MCAD)	14	41
Long-Chain-3-Hydroxyacyl-CoA Dehydrogenase Deficiency (LCHAD)	7	34
Trifunctional Protein Deficiency	14	41
Congenital Lactic Acidosis	21	27
Fumarase Deficiency	21	27
Mitochondrial Complex II Deficiency	21	27
2-Ketoglutarate Dehydrogenase Complex Deficiency	21	27
Pyruvate Dehydrogenase Deficiency (E3)	21	27
Pyruvate Dehydrogenase Deficiency (E2)	21	27
Primary Hyperoxaluria II, PH2	21	39
Pyruvate Kinase Deficiency	21	39
Succinic Semialdehyde Dehydrogenase Deficiency	22	44
Short-Chain 3-Hydroxyacyl-CoA Dehydrogenase Deficiency (SCHAD)	8	18
Succinyl CoA: 3-Ketoacid CoA Transferase Deficiency	4	13
Pyridoxine Dependency with Seizures	13	24
Warburg Effect	46	52
2-Aminoadipic 2-Oxoadipic Aciduria	13	24
3-Phosphoglycerate Dehydrogenase Deficiency	24	52
Fatty Acid Oxidation	7	9
TCA Cycle	18	25
Glycolysis and Pyruvate Dehydrogenase	24	28
Arginine Metabolism	28	48
Ornithine Metabolism	16	31
D-Glucarate and D-Galactarate Degradation	10	22
Palmitate Biosynthesis	11	16
Fatty Acid Elongation (Saturated)	12	14
Cysteine Biosynthesis	13	29
Serine Biosynthesis and Metabolism	10	20
Leucine Biosynthesis	8	16
Threonine Biosynthesis	11	23
Glycolate and Glyoxylate Degradation	15	22
Lipopolysaccharide Biosynthesis	41	53
Quorum Sensing	10	20
S-Adenosyl-L-Methionine Biosynthesis	8	17
Amino Sugar and Nucleotide Sugar Metabolism I	17	33
Peptidoglycan Biosynthesis I	30	36
Fructose Metabolism	15	20
Glycerol Metabolism	30	28
Glycerol Metabolism II	29	30
Glycerol Metabolism III (sn-Glycero-3-Phosphoethanolamine)	30	30
Glycerol Metabolism IV (Glycerophosphoglycerol)	30	30
Glycerol Metabolism V (Glycerophosphoserine)	30	30
Secondary Metabolites: Enterobacterial Common Antigen Biosynthesis	9	17
Secondary Metabolites: Glyoxylate Cycle	7	15
Secondary Metabolites: Cysteine Biosynthesis from Serine	7	20
Secondary Metabolites: Valine and L-Leucine Biosynthesis from Pyruvate	10	24
Secondary Metabolites: Leucine Biosynthesis	7	16
TCA cycle (ubiquinol-2)	18	24
TCA cycle (ubiquinol-3)	18	23
TCA cycle (ubiquinol-4)	18	24
TCA cycle (ubiquinol-5)	18	23
TCA cycle (ubiquinol-6)	18	25
TCA cycle (ubiquinol-7)	18	25
TCA cycle (ubiquinol-8)	18	25
TCA cycle (ubiquinol-9)	18	23
TCA cycle (ubiquinol-10)	18	24
fatty acid oxidation (Butanoate)	6	13
fatty acid oxidation (Decanoate)	6	14
fatty acid oxidation (hexanoate)	6	14
Fatty Acid Oxidation (Laurate)	6	14
fatty acid oxidation (myristate)	6	14
fatty acid oxidation (octanoate)	6	14
fatty acid oxidation (palmitate)	6	14
fatty acid oxidation (steareate)	6	13
2-Oxopent-4-enoate Metabolism	17	25
Lipopolysaccharide Biosynthesis II	40	53
Tryptophan Metabolism II	6	23
Glycolate and Glyoxylate Degradation II	12	21
TCA cycle (ubiquinol-0)	18	25
Phenylethylamine Metabolism	12	26
2-Oxopent-4-enoate Metabolism 2	17	25
Palmitate Biosynthesis 2	10	16
Secondary Metabolites: Enterobacterial Common Antigen Biosynthesis 2	9	17
Secondary Metabolites: Enterobacterial Common Antigen Biosynthesis 3	8	20
Lipopolysaccharide Biosynthesis III	33	52
Peptidoglycan Biosynthesis II	30	37
1,6-Anhydro-N-acetylmuramic Acid Recycling	9	20
Biotin-Carboxyl Carrier Protein Assembly	7	11
Pyruvate Decarboxylation to Acetyl-CoA	3	7
O-Antigen Building Blocks Biosynthesis	9	22
Acetate Metabolism	6	11
The Oncogenic Action of 2-Hydroxyglutarate	27	34
The Oncogenic Action of Succinate	29	33
The Oncogenic Action of Fumarate	29	34
Glutaminolysis and Cancer	35	36
Methionine Metabolism and Salvage	15	34
Threonine Metabolism	6	19
Amino Sugar and Nucleotide Sugar Metabolism	22	29
Glyoxylate Cycle	6	13
Lysine Metabolism	7	22
The Oncogenic Action of L-2-Hydroxyglutarate in Hydroxyglutaric aciduria	28	35
The Oncogenic Action of D-2-Hydroxyglutarate in Hydroxyglutaric aciduria	29	36
Fatty Acid Elongation In Mitochondria	3	34
Terpenoid Backbone Biosynthesis	13	22
Glutamine Metabolism	22	25
Cholesterol biosynthesis and metabolism CE(14:0)	22	50
Cholesterol biosynthesis and metabolism CE(10:0)	22	50
Cholesterol Biosynthesis and Metabolism CE(12:0)	22	50
Cholesterol Biosynthesis and Metabolism CE(16:0)	22	50
Cholesterol biosynthesis and metabolism CE(18:0)	22	50
Fatty Acid Beta-Oxidation I	5	11
Butanoate Metabolism	9	22
2-Methyl-3-hydroxybutryl-CoA Dehydrogenase Deficiency	29	52
Aminosugars metabolism ( Aminosugars metabolism )	15	29
Arginine and Proline metabolism ( Arginine and Proline metabolism )	42	55
Acetyl-CoA + Dihydro-lipoamide = CoA + 6-S-Acetyl-dihydro-lipoamide ( Pyruvate metabolism )	2	4
Butanoate metabolism ( Butanoate metabolism )	15	18
2 Acetyl-CoA = CoA + Acetoacetyl-CoA ( Tryptophan degradation )	2	3
(S)-3-Hydroxy-3-methyl-glutaryl-CoA = Acetyl-CoA + Acetoacetic acid ( Valine,Leucine and Isoleucine degradation )	1	3
Citrate cycle ( Citrate cycle )	21	29
ATP + CoA + Citric acid = ADP + Acetyl-CoA + Oxaloacetic acid + Orthophosphate ( Lysine degradation )	1	7
Glycine and Serine metabolism ( Glycine and Serine metabolism )	36	49
Acetyl-CoA + Glycine = CoA + L-2-Amino-3-oxo-butanoic acid ( Glycine and Serine metabolism )	1	4
Lysine degradation ( Lysine degradation )	20	29
Pyruvate metabolism ( Pyruvate metabolism )	30	27
Malonyl-CoA = Acetyl-CoA + CO2 ( Pyruvate metabolism )	1	3
Tryptophan degradation ( Tryptophan degradation )	64	54
Valine,Leucine and Isoleucine degradation ( Valine,Leucine and Isoleucine degradation )	29	36
Cholesterol metabolism with Bloch and Kandutsch-Russell pathways	0	39
Ketogenesis and ketolysis	8	9
Cholesterol Biosynthesis and Metabolism	22	48
Chitin Biosynthesis	9	21
LPS and Citrate Signaling and Inflammation	23	11
Mevalonate Pathway	11	26
Citrate Cycle	19	30
L-Homomethionine Biosynthesis	6	15
Jasmonic Acid Biosynthesis	9	33
alpha-Linolenic Acid Metabolism	10	20
TCA Cycle (Ubiquinol-2)	4	24
TCA Cycle (Ubiquinol-3)	4	23
TCA Cycle (Ubiquinol-4)	4	24
TCA Cycle (Ubiquinol-5)	4	23
TCA Cycle (Ubiquinol-6)	4	25
TCA Cycle (Ubiquinol-7)	4	25
TCA Cycle (Ubiquinol-8)	4	25
TCA Cycle (Ubiquinol-9)	4	23
TCA Cycle (Ubiquinol-10)	4	24
Fatty Acid Oxidation (Butanoate)	1	13
Fatty Acid Oxidation (Decanoate)	2	14
Fatty Acid Oxidation (Hexanoate)	2	14
Fatty Acid Oxidation (Myristate)	2	14
Fatty Acid Oxidation (Octanoate)	2	14
Fatty Acid Oxidation (Palmitate)	2	14
Fatty Acid Oxidation (Steareate)	2	14
TCA Cycle (Ubiquinol-0)	4	25
Mitochondrial fatty acid synthesis pathway	0	8
TCA cycle in senescence	0	11
Kynurenine pathway and links to cell senescence	20	24
Peptidoglycan cytoplasmic synthesis and recycling pathways	8	34
Neuroinflammation and glutamatergic signaling	1	22
Disorders in ketolysis	5	8
Cholesterol synthesis disorders	0	15
Glucose metabolism in triple-negative breast cancer cells	0	6
Metabolic reprogramming in pancreatic cancer	42	23
Mitochondrial beta-oxidation	0	64
Cholestasis	17	6
Mevalonate pathway	0	10
Metabolic pathways of fibroblasts	17	18
Cholesterol biosynthesis pathway in hepatocytes	11	37
Ergosterol biosynthesis	3	32
TCA cycle (plant)	1	21
Metabolic Epileptic Disorders	25	89
Mycobacterium tuberculosis biological processes	39	62
Mycothiol metabolism	8	28
Mycothiol biosynthesis	6	19
Sulfur compound metabolism	19	29
Cysteine synthesis from O-acetylserine	7	15
lactate oxidation	0	16
acetate formation from acetyl-CoA I	0	8
fatty acid u03B2-oxidation II (core pathway)	0	11
oxidative ethanol degradation III (microsomal)	0	15
ethanol degradation IV (peroxisomal)	0	13
isoleucine degradation I	0	18
threonine degradation IV	0	8
superpathway of threonine metabolism	0	34
glutathione-mediated detoxification	0	8
superpathway of glyoxylate cycle	0	24
arginine biosynthesis I	0	27
peptidoglycan and lipid A precursor biosynthesis	0	34
ornithine biosynthesis	0	17
Central carbon metabolism	0	19
SK UDPglcnac	1	9
Statin pathway	0	3
TCA cycle	0	10
Beta-oxidation of unsaturated fatty acids	0	6
Mitochondrial LC-Fatty Acid Beta-Oxidation	0	8
Biosynthesis of the three types of mycolic acids	8	5
Primary carbon metabolism	23	30
Krebs cycle	1	10
TCA cycle (Krebs cycle)	30	19
AtMetExpress overview	0	109
Valine, leucine and isoleucine degradation	0	34
Fatty acid beta-oxidation 2	0	11
Neurotransmitter release cycle	0	21
Glutathione metabolism	0	13
Peroxisomal beta-oxidation of tetracosanoyl-CoA	4	12
Butyrate-induced histone acetylation	2	2
TCA cycle and deficiency of pyruvate dehydrogenase complex (PDHc)	0	15
Glycerophospholipid biosynthetic pathway	32	33
Fatty acid biosynthesis	0	3
Metabolism overview	0	78
Biochemical pathways: part I	0	466
Amino acid metabolism	0	94
Leptin and adiponectin	0	2
Lipid metabolism pathway	0	6
Ethanol effects on histone modifications	0	17
Mevalonate arm of cholesterol biosynthesis pathway with inhibitors	2	14
Pyrimidine metabolism and related diseases	18	44
Metabolic reprogramming in colon cancer	0	29
Thiamine metabolic pathways	1	16
Glycolysis and gluconeogenesis	0	17
Ferroptosis	1	33
Thermogenesis	0	18
Cerebral organic acidurias, including diseases	5	27
Arylamine metabolism	0	3
TCA cycle (aka Krebs or citric acid cycle)	0	24
Effect of L-carnitine on metabolism	0	9

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
N-alpha-acetyltransferase 50	Homo sapiens (human)	Kd	0.0176	0.0176	0.0868	0.1560	AID1658396
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
chromatin remodeling	N-alpha-acetyltransferase 50	Homo sapiens (human)
N-terminal protein amino acid acetylation	N-alpha-acetyltransferase 50	Homo sapiens (human)
establishment of mitotic sister chromatid cohesion	N-alpha-acetyltransferase 50	Homo sapiens (human)
mitotic sister chromatid cohesion, centromeric	N-alpha-acetyltransferase 50	Homo sapiens (human)
mitotic sister chromatid cohesion	N-alpha-acetyltransferase 50	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
peptide alpha-N-acetyltransferase activity	N-alpha-acetyltransferase 50	Homo sapiens (human)
protein binding	N-alpha-acetyltransferase 50	Homo sapiens (human)
histone H4 acetyltransferase activity	N-alpha-acetyltransferase 50	Homo sapiens (human)
peptidyl-lysine acetyltransferase activity	N-alpha-acetyltransferase 50	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
nucleus	N-alpha-acetyltransferase 50	Homo sapiens (human)
nucleolus	N-alpha-acetyltransferase 50	Homo sapiens (human)
cytoplasm	N-alpha-acetyltransferase 50	Homo sapiens (human)
cytosol	N-alpha-acetyltransferase 50	Homo sapiens (human)
extracellular exosome	N-alpha-acetyltransferase 50	Homo sapiens (human)
NatA complex	N-alpha-acetyltransferase 50	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Assay ID	Title	Year	Journal	Article
AID1658396	Binding affinity to full length human N-terminal His-tagged/GST-tagged Naa50 expressed in Escherichia coli BL21(DE3) cells in by SPR analysis	2020	ACS medicinal chemistry letters, Jun-11, Volume: 11, Issue:6	Characterization of Specific
AID1733716	Binding affinity to recombinant NAT10 acetyltransferase domain (494 to 753 residues) (unknown origin) by isothermal titration calorimetry	2021	ACS medicinal chemistry letters, Jun-10, Volume: 12, Issue:6	Remodelin Is a Cryptic Assay Interference Chemotype That Does Not Inhibit NAT10-Dependent Cytidine Acetylation.
AID1658392	Binding affinity to full length human N-terminal His-tagged/GST-tagged Naa50 expressed in Escherichia coli BL21(DE3) cells assessed as association rate constant by SPR analysis	2020	ACS medicinal chemistry letters, Jun-11, Volume: 11, Issue:6	Characterization of Specific
AID1658390	Binding affinity to full length human N-terminal His-tagged/GST-tagged Naa50 expressed in Escherichia coli BL21(DE3) cells assessed as association rate constant by SPR analysis	2020	ACS medicinal chemistry letters, Jun-11, Volume: 11, Issue:6	Characterization of Specific
AID1733715	Stabilization of full length recombinant NAT10 (unknown origin) by DSLS based analysis	2021	ACS medicinal chemistry letters, Jun-10, Volume: 12, Issue:6	Remodelin Is a Cryptic Assay Interference Chemotype That Does Not Inhibit NAT10-Dependent Cytidine Acetylation.
AID1658394	Binding affinity to full length human N-terminal His-tagged/GST-tagged Naa50 expressed in Escherichia coli BL21(DE3) cells assessed as half life for dissociation by SPR analysis	2020	ACS medicinal chemistry letters, Jun-11, Volume: 11, Issue:6	Characterization of Specific
AID1802403	Isothermal Titration Calorimetry (ITC) from Article 10.1074/jbc.M113.501353: \\Structural, functional, and inhibition studies of a Gcn5-related N-acetyltransferase (GNAT) superfamily protein PA4794: a new C-terminal lysine protein acetyltransferase from ps	2013	The Journal of biological chemistry, Oct-18, Volume: 288, Issue:42	Structural, functional, and inhibition studies of a Gcn5-related N-acetyltransferase (GNAT) superfamily protein PA4794: a new C-terminal lysine protein acetyltransferase from pseudomonas aeruginosa.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1134 (32.75)	18.7374
1990's	451 (13.02)	18.2507
2000's	516 (14.90)	29.6817
2010's	923 (26.65)	24.3611
2020's	439 (12.68)	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	14 (0.39%)	5.53%
Reviews	323 (9.10%)	6.00%
Case Studies	5 (0.14%)	4.05%
Observational	1 (0.03%)	0.25%
Other	3,208 (90.34%)	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.	9.17	54	5	O-acylcarnitine	human metabolite
chloroacetaldehyde [no description available]	2.04	1	0	organochlorine compound
tartronic acid hydroxymalonic acid : A dicarboxylic acid that is malonic acid substituted by a hydroxy group at position 2.	2.43	2	0	dicarboxylic acid; dicarboxylic fatty acid	plant metabolite
2-oxo-3-methylvalerate alpha-keto-beta-methylvaleric acid: RN given refers to parent cpd. 3-methyl-2-oxovaleric acid : A 2-oxo monocarboxylic acid that is valeric acid carrying oxo- and methyl substituents at C-2 and C-3, respectively. An alpha-keto acid analogue and metabolite of isoleucine in man, animals and bacteria. Used as a clinical marker for maple syrup urine disease (MSUD).	1.97	1	0	2-oxo monocarboxylic acid; branched-chain keto acid	human metabolite
alpha-ketoisovalerate alpha-ketoisovalerate: RN given refers to parent cpd. 3-methyl-2-oxobutanoate : A 2-oxo monocarboxylic acid anion that is the conjugate base of 3-methyl-2-oxobutanoic acid, arising from deprotonation of the carboxy group.. 3-methyl-2-oxobutanoic acid : A 2-oxo monocarboxylic acid that is the 2-oxo derivative of isovaleric acid.	2.67	3	0	2-oxo monocarboxylic acid; branched-chain keto acid	human metabolite; Saccharomyces cerevisiae metabolite
alpha-ketobutyric acid alpha-ketobutyric acid: RN given refers to parent cpd; structure. 2-oxobutanoic acid : A 2-oxo monocarboxylic acid that is the 2-oxo derivative of butanoic acid.	2.4	2	0	2-oxo monocarboxylic acid; short-chain fatty acid
2-keto-4-methylvalerate alpha-ketoisocaproic acid: RN given refers to parent cpd. 4-methyl-2-oxopentanoate : A 2-oxo monocarboxylic acid anion that is the conjugate base of 4-methyl-2-oxopentanoic acid.. 4-methyl-2-oxopentanoic acid : A 2-oxo monocarboxylic acid that is pentanoic acid (valeric acid) substituted with a keto group at C-2 and a methyl group at C-4. A metabolite that has been found to accumulate in maple syrup urine disease.	3.26	6	0	2-oxo monocarboxylic acid; branched-chain keto acid	algal metabolite; human metabolite
alpha-ketoadipic acid 2-oxoadipic acid : An oxo dicarboxylic acid that is adipic acid substituted by an oxo group at position 2.	2.38	2	0	oxo dicarboxylic acid	human urinary metabolite; mouse 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.	1.97	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-oxoadipic acid 3-oxoadipic acid: RN given refers to parent cpd. 3-oxoadipic acid : An oxo dicarboxylic acid consisting of adipic acid having a single oxo group at the 3-position.	2.41	2	0	dicarboxylic fatty acid; oxo dicarboxylic acid	bacterial xenobiotic metabolite; human metabolite
acetoacetic acid acetoacetic acid : A 3-oxo monocarboxylic acid that is butyric acid bearing a 3-oxo substituent.	6.25	28	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.	4.17	6	0	amino acid zwitterion; gamma-amino acid; monocarboxylic acid	human metabolite; neurotransmitter; Saccharomyces cerevisiae metabolite; signalling molecule
4-hydroxybenzoic acid 4-hydroxybenzoic acid : A monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring.	1.97	1	0	monohydroxybenzoic acid	algal metabolite; plant metabolite
5-hydroxytryptophan 5-Hydroxytryptophan: The immediate precursor in the biosynthesis of SEROTONIN from tryptophan. It is used as an antiepileptic and antidepressant.. 5-hydroxytryptophan : A tryptophan derivative that is tryptophan substituted by a hydroxy group at position 5.	2.36	2	0	hydroxytryptophan	human metabolite; neurotransmitter
ethylene glycol Ethylene Glycol: A colorless, odorless, viscous dihydroxy alcohol. It has a sweet taste, but is poisonous if ingested. Ethylene glycol is the most important glycol commercially available and is manufactured on a large scale in the United States. It is used as an antifreeze and coolant, in hydraulic fluids, and in the manufacture of low-freezing dynamites and resins.. ethanediol : Any diol that is ethane or substituted ethane carrying two hydroxy groups.. ethylene glycol : A 1,2-glycol compound produced via reaction of ethylene oxide with water.	1.97	1	0	ethanediol; glycol	metabolite; mouse metabolite; solvent; toxin
acetic acid Acetic Acid: Product of the oxidation of ethanol and of the destructive distillation of wood. It is used locally, occasionally internally, as a counterirritant and also as a reagent. (Stedman, 26th ed). acetic acid : A simple monocarboxylic acid containing two carbons.	8.17	53	0	monocarboxylic acid	antimicrobial food preservative; Daphnia magna metabolite; food acidity regulator; protic solvent
acetaldehyde Acetaldehyde: A colorless, flammable liquid used in the manufacture of acetic acid, perfumes, and flavors. It is also an intermediate in the metabolism of alcohol. It has a general narcotic action and also causes irritation of mucous membranes. Large doses may cause death from respiratory paralysis.. acetaldehyde : The aldehyde formed from acetic acid by reduction of the carboxy group. It is the most abundant carcinogen in tobacco smoke.. aldehyde : A compound RC(=O)H, in which a carbonyl group is bonded to one hydrogen atom and to one R group.. acetyl group : A group, formally derived from acetic acid by dehydroxylation, which is fundamental to the biochemistry of all forms of life. When bound to coenzyme A, it is central to the metabolism of carbohydrates and fats.	5.48	21	0	aldehyde	carcinogenic agent; EC 3.5.1.4 (amidase) inhibitor; electron acceptor; Escherichia coli metabolite; human metabolite; mouse metabolite; mutagen; oxidising agent; Saccharomyces cerevisiae metabolite; teratogenic agent
acetoin [no description available]	1.97	1	0	methyl ketone; secondary alpha-hydroxy ketone	metabolite
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	4.9	11	0	ketone body; methyl ketone; propanones; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; human metabolite; polar aprotic solvent
acetyl phosphate acetyl dihydrogen phosphate : An acyl monophosphate in which the acyl group specified is acetyl.	4.09	15	0	acyl monophosphate	Escherichia coli metabolite; human metabolite; mouse metabolite
adenine [no description available]	3.48	2	0	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
adipic acid adipic acid : An alpha,omega-dicarboxylic acid that is the 1,4-dicarboxy derivative of butane.	3.1	5	0	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	food acidity regulator; human xenobiotic metabolite
aminoacetone aminoacetone: RN given refers to parent cpd. aminoacetone : A propanone consisting of acetone having an amino group at the 1-position.	2.72	3	0	methyl ketone; propanones	Escherichia coli metabolite; mouse metabolite
ammonium hydroxide azane : Saturated acyclic nitrogen hydrides having the general formula NnHn+2.	8.08	17	1	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.	2.03	1	0	aminobenzoic acid	human metabolite; mouse metabolite
arsenic acid arsenic acid: RN given refers to orthoarsenic acid(H3AsO4); see also sodium arsenate. arsenic acid : An arsenic oxoacid comprising one oxo group and three hydroxy groups attached to a central arsenic atom.	1.93	1	0	arsenic oxoacid	Escherichia coli metabolite
beta-alanine [no description available]	4.2	4	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.	3.36	7	0	benzoic acids	algal metabolite; antimicrobial food preservative; drug allergen; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 3.1.1.3 (triacylglycerol lipase) inhibitor; human xenobiotic metabolite; plant metabolite
betaine glycine betaine : The amino acid betaine derived from glycine.	3.25	6	0	amino-acid betaine; glycine derivative	fundamental metabolite
bromide Bromides: Salts of hydrobromic acid, HBr, with the bromine atom in the 1- oxidation state. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	1.95	1	0	halide anion; monoatomic bromine
2,3-butylene glycol 2,3-butylene glycol: RN given refers to cpd without isomeric designation. butane-2,3-diol : A butanediol in which hydroxylation is at C-2 and C-3.	2.21	1	0	butanediol; glycol; secondary alcohol
1-butanol 1-Butanol: A four carbon linear hydrocarbon that has a hydroxy group at position 1.. butan-1-ol : A primary alcohol that is butane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It it produced in small amounts in humans by the gut microbes.	4.13	15	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.	3.23	6	0	fatty acid 4:0; straight-chain saturated fatty acid	human urinary metabolite; Mycoplasma genitalium metabolite
cadaverine [no description available]	2.38	2	0	alkane-alpha,omega-diamine	Daphnia magna metabolite; Escherichia coli metabolite; mouse metabolite; plant metabolite
carbamates [no description available]	2.25	1	0	amino-acid anion
carbamyl phosphate Carbamyl Phosphate: The monoanhydride of carbamic acid with PHOSPHORIC ACID. It is an important intermediate metabolite and is synthesized enzymatically by CARBAMYL-PHOSPHATE SYNTHASE (AMMONIA) and CARBAMOYL-PHOSPHATE SYNTHASE (GLUTAMINE-HYDROLYZING).	3.1	5	0	acyl monophosphate; one-carbon compound	Escherichia coli metabolite; mouse metabolite
carbon monoxide Carbon Monoxide: Carbon monoxide (CO). A poisonous colorless, odorless, tasteless gas. It combines with hemoglobin to form carboxyhemoglobin, which has no oxygen carrying capacity. The resultant oxygen deprivation causes headache, dizziness, decreased pulse and respiratory rates, unconsciousness, and death. (From Merck Index, 11th ed). carbon monoxide : A one-carbon compound in which the carbon is joined only to a single oxygen. It is a colourless, odourless, tasteless, toxic gas.	7.22	40	0	carbon oxide; gas molecular entity; one-carbon compound	biomarker; EC 1.9.3.1 (cytochrome c oxidase) inhibitor; human metabolite; ligand; metabolite; mitochondrial respiratory-chain inhibitor; mouse metabolite; neurotoxin; neurotransmitter; P450 inhibitor; probe; signalling molecule; vasodilator agent
formic acid formic acid: RN given refers to parent cpd. formic acid : The simplest carboxylic acid, containing a single carbon. Occurs naturally in various sources including the venom of bee and ant stings, and is a useful organic synthetic reagent. Principally used as a preservative and antibacterial agent in livestock feed. Induces severe metabolic acidosis and ocular injury in human subjects.	4.72	9	0	monocarboxylic acid	antibacterial agent; astringent; metabolite; protic solvent; solvent
carnitine [no description available]	17.71	130	1	amino-acid betaine	human metabolite; mouse metabolite
catechol [no description available]	1.98	1	0	catechols	allelochemical; genotoxin; plant metabolite
methane Methane: The simplest saturated hydrocarbon. It is a colorless, flammable gas, slightly soluble in water. It is one of the chief constituents of natural gas and is formed in the decomposition of organic matter. (Grant & Hackh's Chemical Dictionary, 5th ed). methane : A one-carbon compound in which the carbon is attached by single bonds to four hydrogen atoms. It is a colourless, odourless, non-toxic but flammable gas (b.p. -161degreeC).	6.17	24	0	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
choline [no description available]	8.49	59	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.	1.95	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.	11.56	74	1	tricarboxylic acid	antimicrobial agent; chelator; food acidity regulator; fundamental metabolite
chlorine chloride : A halide anion formed when chlorine picks up an electron to form an an anion.	4.31	6	0	halide anion; monoatomic chlorine	cofactor; Escherichia coli metabolite; human 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).	2.13	1	0	monohydroxybenzoic acid	algal metabolite; antifungal agent; antiinfective agent; EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor; keratolytic drug; plant hormone; plant metabolite
phloroglucinol Phloroglucinol: A trinitrobenzene derivative with antispasmodic properties that is used primarily as a laboratory reagent.. phloroglucinol : A benzenetriol with hydroxy groups at position 1, 3 and 5.	2.72	3	0	benzenetriol; phenolic donor	algal 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.	5	15	0	medium-chain fatty acid; straight-chain saturated fatty acid	antibacterial agent; Escherichia coli metabolite; human metabolite
malyl-coenzyme a [no description available]	3.12	5	0
hydrogen sulfide Hydrogen Sulfide: A flammable, poisonous gas with a characteristic odor of rotten eggs. It is used in the manufacture of chemicals, in metallurgy, and as an analytical reagent. (From Merck Index, 11th ed). hydrogen sulfide : A sulfur hydride consisting of a single sulfur atom bonded to two hydrogen atoms. A highly poisonous, flammable gas with a characteristic odour of rotten eggs, it is often produced by bacterial decomposition of organic matter in the absence of oxygen.. thiol : An organosulfur compound in which a thiol group, -SH, is attached to a carbon atom of any aliphatic or aromatic moiety.	2	1	0	gas molecular entity; hydracid; mononuclear parent hydride; sulfur hydride	Escherichia coli metabolite; genotoxin; metabolite; signalling molecule; toxin; vasodilator agent
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.	9.12	34	3	(omega-1)-hydroxy fatty acid; 3-hydroxy monocarboxylic acid; hydroxybutyric acid	human metabolite
hippuric acid hippuric acid: RN given refers to parent cpd; structure in Merck Index, 9th ed, #4591. N-benzoylglycine : An N-acylglycine in which the acyl group is specified as benzoyl.	1.96	1	0	N-acylglycine	human blood serum metabolite; uremic toxin
2-aminoadipic acid 2-Aminoadipic Acid: A metabolite in the principal biochemical pathway of lysine. It antagonizes neuroexcitatory activity modulated by the glutamate receptor, N-METHYL-D-ASPARTATE; (NMDA).. 2-aminoadipic acid : An alpha-amino acid that is adipic acid bearing a single amino substituent at position 2. An intermediate in the formation of lysine.	3.59	2	0	amino dicarboxylic acid; dicarboxylic fatty acid; non-proteinogenic alpha-amino acid	Caenorhabditis elegans metabolite; mammalian metabolite
2-keto-4-methylthiobutyric acid 2-keto-4-methylthiobutyric acid: RN given refers to parent cpd; structure. 4-methylthio-2-oxobutanoic acid : A 2-oxo monocarboxylic acid derived from L-methionine via the action of methionine transaminase.	2.02	1	0	omega-(methylthio)-2-oxocarboxylic acid
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.	1.95	1	0	C4-dicarboxylic acid	human metabolite
n(1)-acetylspermidine N(1)-acetylspermidine : An acetylspermidine having the acetyl group at the N1-position.	1.99	1	0	acetylspermidine	Escherichia coli metabolite; metabolite
2-methylcitric acid 2-methylcitric acid: RN given refers to parent cpd	2.05	1	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.	4.89	34	0	2-hydroxydicarboxylic acid; C4-dicarboxylic acid	food acidity regulator; fundamental metabolite
phosphoglycolate phosphoglycolate: RN given refers to parent acid. 2-phosphoglycolic acid : The O-phospho derivative of glycolic acid.	2.25	1	0	carboxyalkyl phosphate	Escherichia coli metabolite; mouse 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.	2.06	1	0	monocarboxylic acid; phosphonic acids	antiviral agent; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor
3-methylthiopropionate 3-(methylthio)propionic acid : A thia fatty acid acid consisting of propionic acid with a methylthio substituent at the 3-position; an intermediate in mammalian methionine metabolism in vitro. The simplest known phytotoxin, it is a blight-inducing toxin produced by the cassava pathogen Xanthomonas campestris manihotis.	2	1	0	thia fatty acid	phytotoxin
aminocaproic acid Aminocaproic Acid: An antifibrinolytic agent that acts by inhibiting plasminogen activators which have fibrinolytic properties.. 6-aminohexanoic acid : An epsilon-amino acid comprising hexanoic acid carrying an amino substituent at position C-6. Used to control postoperative bleeding, and to treat overdose effects of the thrombolytic agents streptokinase and tissue plasminogen activator.	2.13	1	0	amino acid zwitterion; epsilon-amino acid; omega-amino fatty acid	antifibrinolytic drug; hematologic agent; metabolite
creatine [no description available]	1.95	1	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.	12.33	83	6	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
5,6-dihydroorotate 4,5-dihydroorotic acid: RN given refers to cpd without isomeric designation; structure. dihydroorotic acid : A pyrimidinemonocarboxylic acid that results from the base-catalysed cyclisation of N(alpha)-carbethoxyasparagine.	2.21	1	0	monocarboxylic acid; N-acylurea; pyrimidinemonocarboxylic acid; secondary amide
diacetyl butane-2,3-dione : An alpha-diketone that is butane substituted by oxo groups at positions 2 and 3. It is a metabolite produced during the malolactic fermentation.	2.65	3	0	alpha-diketone	Escherichia coli metabolite; Saccharomyces cerevisiae metabolite
dihydrolipoamide [no description available]	1.99	1	0	dithiol; monocarboxylic acid amide	cofactor; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
dihydroxyacetone phosphate Dihydroxyacetone Phosphate: An important intermediate in lipid biosynthesis and in glycolysis.. dihydroxyacetone phosphate : A member of the class of glycerone phosphates that consists of glycerone bearing a single phospho substituent.	2.38	2	0	glycerone phosphates; primary alpha-hydroxy ketone	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
dimethylglycine dimethylglycine: metabolic product of calcium pangamate; mutagen when mixed with nitrite; RN given refers to parent cpd. N,N-dimethylglycine : An N-methylglycine that is glycine carrying two N-methyl substituents.	2	1	0	amino acid zwitterion; N-methyl-amino acid; N-methylglycines	Daphnia magna metabolite; human metabolite; mouse metabolite
ethanolamine [no description available]	2.77	3	0	ethanolamines; primary alcohol; primary amine	Escherichia coli metabolite; human metabolite; mouse metabolite
formaldehyde paraform: polymerized formaldehyde; RN given refers to parent cpd; used in root canal therapy	4.01	4	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
3-phosphoglycerate 3-phosphoglycerate : An organic anion obtained by deprotonation of at least one of the acidic groups of 3-phosphoglyceric acid.	2.48	2	0	monophosphoglyceric acid; tetronic acid derivative	algal metabolite; fundamental metabolite
gamma-butyrobetaine 4-(trimethylammonio)butanoate : An amino-acid betaine gamma-aminobutyric acid zwitterion in which all of the hydrogens attached to the nitrogen are replaced by methyl groups.	1.99	1	0	amino-acid betaine	Escherichia coli metabolite; human metabolite
glutaconyl-coenzyme a [no description available]	2.15	1	0
glutaric acid glutaric acid: RN given refers to parent cpd. glutaric acid : An alpha,omega-dicarboxylic acid that is a linear five-carbon dicarboxylic acid.	2.41	2	0	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	Daphnia magna metabolite; human metabolite
glycine [no description available]	5.91	39	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
glyceraldehyde Glyceraldehyde: An aldotriose containing the propionaldehyde structure with hydroxy groups at the 2- and 3-positions. It is involved in the formation of ADVANCED GLYCOSYLATION END PRODUCTS.. glyceraldehyde : An aldotriose comprising propanal having hydroxy groups at the 2- and 3-positions. It plays role in the formation of advanced glycation end-products (AGEs), a deleterious accompaniment to ageing.. aldose : Aldehydic parent sugars (polyhydroxy aldehydes H[CH(OH)]nC(=O)H, n >= 2) and their intramolecular hemiacetals.	2.69	3	0	aldotriose	fundamental metabolite
glycerol Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.	9.28	37	3	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
alpha-glycerophosphoric acid [no description available]	3.5	2	0	glycerol monophosphate	algal metabolite; human metabolite
glycolaldehyde [no description available]	2.21	1	0	glycolaldehydes	fundamental metabolite; human 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.	5.85	30	0	2-oxo monocarboxylic acid; aldehydic acid	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
carbonic acid Carbonic Acid: Carbonic acid (H2C03). The hypothetical acid of carbon dioxide and water. It exists only in the form of its salts (carbonates), acid salts (hydrogen carbonates), amines (carbamic acid), and acid chlorides (carbonyl chloride). (From Grant & Hackh's Chemical Dictionary, 5th ed)	3.45	2	0	carbon oxoacid; chalcocarbonic acid	mouse metabolite
hydrogen carbonate Bicarbonates: Inorganic salts that contain the -HCO3 radical. They are an important factor in determining the pH of the blood and the concentration of bicarbonate ions is regulated by the kidney. Levels in the blood are an index of the alkali reserve or buffering capacity.. hydrogencarbonate : The carbon oxoanion resulting from the removal of a proton from carbonic acid.	5.77	29	0	carbon oxoanion	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
histamine [no description available]	1.95	1	0	aralkylamino compound; imidazoles	human metabolite; mouse metabolite; neurotransmitter
hydrogen Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.	5.98	34	0	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
hydroxylamine amino alcohol : An alcohol containing an amino functional group in addition to the alcohol-defining hydroxy group.	2.11	1	0	hydroxylamines	algal metabolite; bacterial xenobiotic metabolite; EC 1.1.3.13 (alcohol oxidase) inhibitor; EC 4.2.1.22 (cystathionine beta-synthase) inhibitor; EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor; nitric oxide donor; nucleophilic reagent
indoleacetic acid indoleacetic acid: RN given refers to unlabeled parent cpd; structure in Merck Index, 9th ed, #4841. auxin : Any of a group of compounds, both naturally occurring and synthetic, that induce cell elongation in plant stems (from Greek alphaupsilonxialphanuomega, "to grow").. indole-3-acetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group.	2.05	1	0	indole-3-acetic acids; monocarboxylic acid	auxin; human metabolite; mouse metabolite; plant hormone; plant metabolite
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.	2.38	2	0	dicarboxylic acid; dicarboxylic fatty acid; olefinic compound	fungal metabolite; human metabolite
kynurenine Kynurenine: A metabolite of the essential amino acid tryptophan metabolized via the tryptophan-kynurenine pathway.. kynurenine : A ketone that is alanine in which one of the methyl hydrogens is substituted by a 2-aminobenzoyl group.	2.41	1	0	aromatic ketone; non-proteinogenic alpha-amino acid; substituted aniline	human metabolite
lipoamide Lipozyme: lipase from Rhizomucor miehei immobilized on anion exchange resin	2.03	1	0	dithiolanes; monocarboxylic acid amide	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae 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.	5.73	16	0	dithiolanes; heterocyclic fatty acid; thia fatty acid	fundamental metabolite; geroprotector
malonic acid malonic acid : An alpha,omega-dicarboxylic acid in which the two carboxy groups are separated by a single methylene group.. dicarboxylic acid : Any carboxylic acid containing two carboxy groups.	3.47	8	0	alpha,omega-dicarboxylic acid	human metabolite
malonic semialdehyde malonic semialdehyde: RN given refers to parent cpd; structure given in first source	2.63	3	0	aldehydic acid
methylmercaptan methylmercaptan: intermediate in the manufacturing of jet fuels, pesticides, fungicides, plastics, synthesis of methionine; odor may cause nausea; narcotic in high concentrations; depresses urea biosynthesis; RN given refers to parent cpd; structure	2.41	2	0	alkanethiol	human metabolite; Saccharomyces cerevisiae metabolite
pyruvaldehyde Pyruvaldehyde: An organic compound used often as a reagent in organic synthesis, as a flavoring agent, and in tanning. It has been demonstrated as an intermediate in the metabolism of acetone and its derivatives in isolated cell preparations, in various culture media, and in vivo in certain animals.. methylglyoxal : A 2-oxo aldehyde derived from propanal.	2.67	3	0	2-oxo aldehyde; propanals	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
methanol Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.	5.19	15	0	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
inositol Inositol: An isomer of glucose that has traditionally been considered to be a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in man. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1379) Inositol phospholipids are important in signal transduction.. inositol : Any cyclohexane-1,2,3,4,5,6-hexol.. 1D-chiro-inositol : Belonging to the inositol family of compounds, D-chiro-inositol (DCI) is an isomer of glucose. It is an important secondary messenger in insulin signal transduction.. muco-inositol : An inositol that is cyclohexane-1,2,3,4,5,6-hexol having a (1R,2R,3r,4R,5S,6r)-configuration.	2.02	1	0	cyclitol; hexol
methyl coenzyme m methyl coenzyme M: RN & N1 from 9th CI Form Index; RN given refers to parent cpd	3.49	2	0	S-substituted coenzyme M
melatonin [no description available]	6.03	15	0	acetamides; tryptamines	anticonvulsant; central nervous system depressant; geroprotector; hormone; human metabolite; immunological adjuvant; mouse metabolite; radical scavenger
n-acetylserotonin N-acetylserotonin : An N-acylserotonin resulting from the formal condensation of the primary amino group of serotonin with the carboxy group of acetic acid.	2.68	3	0	acetamides; N-acylserotonin; phenols	antioxidant; human metabolite; mouse metabolite; tropomyosin-related kinase B receptor agonist
naphthalene [no description available]	2.15	1	0	naphthalenes; ortho-fused bicyclic arene	apoptosis inhibitor; carcinogenic agent; environmental contaminant; mouse metabolite; plant metabolite; volatile oil component
nickel Nickel: A trace element with the atomic symbol Ni, atomic number 28, and atomic weight 58.69. It is a cofactor of the enzyme UREASE.. nickel ion : A nickel atom having a net electric charge.. nickel atom : Chemical element (nickel group element atom) with atomic number 28.	11.74	24	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.	4.41	4	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.	2.17	1	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.	3.13	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.	1.99	1	0	nitrogen oxoacid	protic solvent; reagent
nitrites Nitrites: Salts of nitrous acid or compounds containing the group NO2-. The inorganic nitrites of the type MNO2 (where M=metal) are all insoluble, except the alkali nitrites. The organic nitrites may be isomeric, but not identical with the corresponding nitro compounds. (Grant & Hackh's Chemical Dictionary, 5th ed)	2.67	3	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species	human metabolite
nitrous oxide Nitrous Oxide: Nitrogen oxide (N2O). A colorless, odorless gas that is used as an anesthetic and analgesic. High concentrations cause a narcotic effect and may replace oxygen, causing death by asphyxia. It is also used as a food aerosol in the preparation of whipping cream.. dinitrogen oxide : A nitrogen oxide consisting of linear unsymmetrical molecules with formula N2O. While it is the most used gaseous anaesthetic in the world, its major commercial use, due to its solubility under pressure in vegetable fats combined with its non-toxicity in low concentrations, is as an aerosol spray propellant and aerating agent for canisters of 'whipped' cream.	1.97	1	0	gas molecular entity; nitrogen oxide	analgesic; bacterial metabolite; food packaging gas; food propellant; general anaesthetic; greenhouse gas; inhalation anaesthetic; NMDA receptor antagonist; raising agent; refrigerant; vasodilator agent
orotic acid Orotic Acid: An intermediate product in PYRIMIDINE synthesis which plays a role in chemical conversions between DIHYDROFOLATE and TETRAHYDROFOLATE.. orotic acid : A pyrimidinemonocarboxylic acid that is uracil bearing a carboxy substituent at position C-6.	2.68	3	0	pyrimidinemonocarboxylic acid	Escherichia coli metabolite; metabolite; mouse 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.	7.81	31	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.	2.71	3	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.	3.47	2	0	dicarboxylic acid monoamide	Escherichia coli metabolite
4-aminobenzoic acid 4-Aminobenzoic Acid: An aminobenzoic acid isomer that combines with pteridine and GLUTAMIC ACID to form FOLIC ACID. The fact that 4-aminobenzoic acid absorbs light throughout the UVB range has also resulted in its use as an ingredient in SUNSCREENS.. 4-ammoniobenzoate : A zwitterion obtained by transfer of a proton from the carboxy to the amino group of 4-aminobenzoic acid.. 4-aminobenzoic acid : An aminobenzoic acid in which the amino group is para to the carboxy group.	4	14	0	aminobenzoic acid; aromatic amino-acid zwitterion	allergen; Escherichia coli metabolite; plant metabolite
palmitic acid Palmitic Acid: A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids.. hexadecanoic acid : A straight-chain, sixteen-carbon, saturated long-chain fatty acid.	7.54	28	0	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; EC 1.1.1.189 (prostaglandin-E2 9-reductase) inhibitor; plant metabolite
pentachlorophenol PENTA: structure given in first source	1.96	1	0	aromatic fungicide; chlorophenol; organochlorine pesticide; pentachlorobenzenes	human xenobiotic 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.	1.96	1	0	2-oxo monocarboxylic acid	chromogenic compound; EC 6.4.1.1 (pyruvate carboxylase) inhibitor; fundamental metabolite
phenylacetaldehyde [no description available]	1.99	1	0	alpha-CH2-containing aldehyde; phenylacetaldehydes	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
phenylacetic acid phenylacetic acid : A monocarboxylic acid that is toluene in which one of the hydrogens of the methyl group has been replaced by a carboxy group.	4.21	17	0	benzenes; monocarboxylic acid; phenylacetic acids	allergen; Aspergillus metabolite; auxin; EC 6.4.1.1 (pyruvate carboxylase) inhibitor; Escherichia coli metabolite; human metabolite; plant growth retardant; plant metabolite; Saccharomyces cerevisiae metabolite; toxin
phenethylamine phenethylamine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7016. 2-phenylethylamine : A phenylethylamine having the phenyl substituent at the 2-position.	3.5	2	0	alkaloid; aralkylamine; phenylethylamine	Escherichia coli metabolite; human metabolite; mouse metabolite
phosphoenolpyruvate Phosphoenolpyruvate: A monocarboxylic acid anion derived from selective deprotonation of the carboxy group of phosphoenolpyruvic acid. It is a metabolic intermediate in GLYCOLYSIS; GLUCONEOGENESIS; and other pathways.. phosphoenolpyruvate : A monocarboxylic acid anion resuting from selective deprotonation of the carboxy group of phosphoenolpyruvic acid.. phosphoenolpyruvic acid : A monocarboxylic acid that is acrylic acid substituted by a phosphonooxy group at position 2. It is a metabolic intermediate in pathways like glycolysis and gluconeogenesis.	4.71	30	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.	1.96	1	0	phosphocholines	allergen; epitope; hapten; human metabolite; mouse metabolite
phthalic acid phthalic acid: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7178. phthalic acid : A benzenedicarboxylic acid cosisting of two carboxy groups at ortho positions.	2.41	1	0	benzenedicarboxylic acid	human xenobiotic metabolite
diphosphoric acid diphosphoric acid : An acyclic phosphorus acid anhydride obtained by condensation of two molecules of phosphoric acid.	2.52	2	0	acyclic phosphorus acid anhydride; phosphorus oxoacid	Escherichia coli metabolite
pqq cofactor PQQ Cofactor: A pyrrolo-quinoline having two adjacent keto-groups at the 4 and 5 positions and three acidic carboxyl groups. It is a coenzyme of some DEHYDROGENASES.. pyrroloquinoline quinone : A pyrroloquinoline having oxo groups at the 4- and 5-positions and carboxy groups at the 2-, 7- and 9-positions.	1.98	1	0	orthoquinones; pyrroloquinoline cofactor; tricarboxylic acid	anti-inflammatory agent; antioxidant; cofactor; water-soluble vitamin (role)
propylene glycol Propylene Glycol: A clear, colorless, viscous organic solvent and diluent used in pharmaceutical preparations.. propane-1,2-diol : The simplest member of the class of propane-1,2-diols, consisting of propane in which a hydrogen at position 1 and a hydrogen at position 2 are substituted by hydroxy groups. A colourless, viscous, hygroscopic, low-melting (-59degreeC) and high-boiling (188degreeC) liquid with low toxicity, it is used as a solvent, emulsifying agent, and antifreeze.	2.57	2	0	glycol; propane-1,2-diols	allergen; human xenobiotic metabolite; mouse metabolite; protic solvent
1-propanol 1-Propanol: A colorless liquid made by oxidation of aliphatic hydrocarbons that is used as a solvent and chemical intermediate.. propan-1-ol : The parent member of the class of propan-1-ols that is propane in which a hydrogen of one of the methyl groups is replaced by a hydroxy group.	1.99	1	0	propan-1-ols; short-chain primary fatty alcohol	metabolite; protic solvent
propionic acid propionic acid : A short-chain saturated fatty acid comprising ethane attached to the carbon of a carboxy group.	7.17	19	2	saturated fatty acid; short-chain fatty acid	antifungal drug
pteridines [no description available]	1.97	1	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; pteridines
purine 1H-purine : The 1H-tautomer of purine.. 3H-purine : The 3H-tautomer of purine.. 9H-purine : The 9H-tautomer of purine.. 7H-purine : The 7H-tautomer of purine.	2.49	2	0	purine
putrescine [no description available]	3.06	5	0	alkane-alpha,omega-diamine	antioxidant; fundamental metabolite
pyrazinamide pyrazinecarboxamide : A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of pyrazinoic acid (pyrazine-2-carboxylic acid) with ammonia. A prodrug for pyrazinoic acid, pyrazinecarboxamide is used as part of multidrug regimens for the treatment of tuberculosis.	2.06	1	0	monocarboxylic acid amide; N-acylammonia; pyrazines	antitubercular agent; prodrug
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.	8.06	5	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.	14.32	193	2	2-oxo monocarboxylic acid	cofactor; fundamental metabolite
dimethyl sulfide dimethyl sulfide: structure. dimethyl sulfide : A methyl sulfide in which the sulfur atom is substituted by two methyl groups. It is produced naturally by some marine algae.. methyl sulfide : Any aliphatic sulfide in which at least one of the organyl groups attached to the sulfur is a methyl group.	2.25	1	0	aliphatic sulfide	algal metabolite; bacterial xenobiotic metabolite; EC 3.5.1.4 (amidase) inhibitor; Escherichia coli metabolite; marine metabolite
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.	2.04	1	0	divalent inorganic anion; sulfur oxide; sulfur oxoanion	human metabolite
dithionite Dithionite: Dithionite. The dithionous acid ion and its salts.	1.99	1	0	sulfur oxide; sulfur oxoanion
sarcosine cocobetaine: N-alkyl-betaine; cause of shampoo dermatitis	2	1	0	N-alkylglycine zwitterion; N-alkylglycine; N-methyl-amino acid; N-methylglycines	Escherichia coli metabolite; glycine receptor agonist; glycine transporter 1 inhibitor; human metabolite; mouse metabolite
sulfites Sulfites: Inorganic salts of sulfurous acid.. sulfites : Any sulfurous acid derivative that is a salt or an ester of sulfurous acid.. organosulfonate oxoanion : An organic anion obtained by deprotonation of the sufonate group(s) of any organosulfonic acid.. sulfite : A sulfur oxoanion that is the conjugate base of hydrogen sulfite (H2SO3).	2.39	2	0	divalent inorganic anion; sulfur oxide; sulfur oxoanion
spermidine [no description available]	5.53	16	0	polyazaalkane; triamine	autophagy inducer; fundamental metabolite; geroprotector
spermine [no description available]	4.97	12	0	polyazaalkane; tetramine	antioxidant; fundamental metabolite; immunosuppressive agent
succinic acid Succinic Acid: A water-soluble, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. (Hawley's Condensed Chemical Dictionary, 12th ed, p1099; McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed, p1851). succinic acid : An alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle.	7.82	37	0	alpha,omega-dicarboxylic acid; C4-dicarboxylic acid	anti-ulcer drug; fundamental metabolite; micronutrient; nutraceutical; radiation protective agent
taurine [no description available]	2.95	4	0	amino sulfonic acid; zwitterion	antioxidant; Escherichia coli metabolite; glycine receptor agonist; human metabolite; mouse metabolite; nutrient; radical scavenger; Saccharomyces cerevisiae metabolite
thiamine thiamine(1+) : A primary alcohol that is 1,3-thiazol-3-ium substituted by (4-amino-2-methylpyrimidin-5-yl)methyl, methyl and 2-hydroxyethyl groups at positions 3, 4 and 5, respectively.	4.08	4	0	primary alcohol; vitamin B1	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
toluene methylbenzene : Any alkylbenzene that is benzene substituted with one or more methyl groups.	7.68	3	0	methylbenzene; toluenes; volatile organic compound	cholinergic antagonist; fuel additive; neurotoxin; non-polar solvent
tryptamine [no description available]	3.78	11	0	aminoalkylindole; aralkylamino compound; indole alkaloid; tryptamines	human metabolite; mouse metabolite; plant metabolite
uracil 2,4-dihydroxypyrimidine: a urinary biomarker for bipolar disorder	7.66	3	0	pyrimidine nucleobase; pyrimidone	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; prodrug; Saccharomyces cerevisiae metabolite
uric acid Uric Acid: An oxidation product, via XANTHINE OXIDASE, of oxypurines such as XANTHINE and HYPOXANTHINE. It is the final oxidation product of purine catabolism in humans and primates, whereas in most other mammals URATE OXIDASE further oxidizes it to ALLANTOIN.. uric acid : An oxopurine that is the final oxidation product of purine metabolism.. 6-hydroxy-1H-purine-2,8(7H,9H)-dione : A tautomer of uric acid having oxo groups at C-2 and C-8 and a hydroxy group at C-6.. 7,9-dihydro-1H-purine-2,6,8(3H)-trione : An oxopurine in which the purine ring is substituted by oxo groups at positions 2, 6, and 8.	3.77	3	0	uric acid	Escherichia coli metabolite; human metabolite; mouse metabolite
urea pseudourea: clinical use; structure. isourea : A carboximidic acid that is the imidic acid tautomer of urea, H2NC(=NH)OH, and its hydrocarbyl derivatives.	8.08	17	1	isourea; monocarboxylic acid amide; one-carbon compound	Daphnia magna metabolite; Escherichia coli metabolite; fertilizer; flour treatment agent; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
vanillin Vanilla: A plant genus of the family ORCHIDACEAE that is the source of the familiar flavoring used in foods and medicines (FLAVORING AGENTS).	2.71	3	0	benzaldehydes; monomethoxybenzene; phenols	anti-inflammatory agent; anticonvulsant; antioxidant; flavouring agent; plant metabolite
xanthine 7H-xanthine : An oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-7 is protonated.. 9H-xanthine : An oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-9 is protonated.	3.12	1	0	xanthine	Saccharomyces cerevisiae metabolite
isopentenyl pyrophosphate isopentenyl pyrophosphate: substrate for isopentenyl pyrophosphate isomerase; RN given refers to unlabeled cpd; a nonpeptide mycobacterial antigen that stimulates gamma delta T cells. isopentenyl diphosphate : A prenol phosphate comprising 3-methylbut-3-en-1-ol having an O-diphosphate substituent.	4.6	8	0	prenol phosphate	antigen; antioxidant; epitope; Escherichia coli metabolite; mouse metabolite; phosphoantigen
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.	4.03	2	0	secondary alcohol; tricarboxylic acid	fundamental metabolite
normetanephrine Normetanephrine: A methylated metabolite of norepinephrine that is excreted in the urine and found in certain tissues. It is a marker for tumors.	1.95	1	0	catecholamine
mandelic acid SAMMA: mandelic acid condensation polymer	2.1	1	0	2-hydroxy monocarboxylic acid; benzenes	antibacterial agent; human xenobiotic metabolite
1,10-phenanthroline 1,10-phenanthroline: RN given refers to parent cpd; inhibits Zn-dependent metalloproteinases	2.39	2	0	phenanthroline	EC 2.7.1.1 (hexokinase) inhibitor; EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor
1-anilino-8-naphthalenesulfonate 1-anilino-8-naphthalenesulfonate: RN given refers to parent cpd. 8-anilinonaphthalene-1-sulfonic acid : A naphthalenesulfonic acid that is naphthalene-1-sulfonic acid substituted by a phenylamino group at position 8.	4.51	7	0	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
2,4-dichlorophenoxyacetic acid 2,4-Dichlorophenoxyacetic Acid: An herbicide with irritant effects on the eye and the gastrointestinal system.. 2,4-D : A chlorophenoxyacetic acid that is phenoxyacetic acid in which the ring hydrogens at postions 2 and 4 are substituted by chlorines.	3.1	1	0	chlorophenoxyacetic acid; dichlorobenzene	agrochemical; defoliant; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; environmental contaminant; phenoxy herbicide; synthetic auxin
2,4-dinitrophenol 2,4-Dinitrophenol: A toxic dye, chemically related to trinitrophenol (picric acid), used in biochemical studies of oxidative processes where it uncouples oxidative phosphorylation. It is also used as a metabolic stimulant. (Stedman, 26th ed). dinitrophenol : Members of the class of nitrophenol carrying two nitro substituents.. 2,4-dinitrophenol : A dinitrophenol having the nitro groups at the 2- and 4-positions.	2.36	2	0	dinitrophenol	allergen; antiseptic drug; bacterial xenobiotic metabolite; geroprotector; oxidative phosphorylation inhibitor
2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine: mutagen from fried ground beef; structure given in first source. PhIP : An imidazopyridine that is 1H--imidazo[4,5-b]pyridine which is substituted at positions 1, 2, and 6 by methyl, amino, and phenyl groups, respectively. It is the most abundant of the mutagenic heterocyclic amines found in cooked meat and fish.	2.4	2	0	imidazopyridine; primary amino compound	carcinogenic agent; mutagen
2-aminofluorene [no description available]	3.78	11	0
mercaptoethanol Mercaptoethanol: A water-soluble thiol derived from hydrogen sulfide and ethanol. It is used as a reducing agent for disulfide bonds and to protect sulfhydryl groups from oxidation.	3.57	9	0	alkanethiol; primary alcohol	geroprotector
meglutol Meglutol: An antilipemic agent which lowers cholesterol, triglycerides, serum beta-lipoproteins and phospholipids. It acts by interfering with the enzymatic steps involved in the conversion of acetate to hydroxymethylglutaryl coenzyme A as well as inhibiting the activity of HYDROXYMETHYLGLUTARYL COA REDUCTASES which is the rate limiting enzyme in the biosynthesis of cholesterol.. 3-hydroxy-3-methylglutaric acid : A dicarboxylic acid that is glutaric acid in which one of the two hydrogens at position 3 is substituted by a hydroxy group, while the other is substituted by a methyl group. It has been found to accumulate in urine of patients suffering from HMG-CoA lyase (3-hydroxy-3-methylglutaryl-CoA lyase, EC 4.1.3.4) deficiency. It occurs as a plant metabolite in Crotalaria dura.	4.48	4	0	3-hydroxy carboxylic acid; dicarboxylic acid; tertiary alcohol	anticholesteremic drug; antimetabolite; EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor; human metabolite; plant metabolite
3-methylcholanthrene Methylcholanthrene: A carcinogen that is often used in experimental cancer studies.. 3-methylcholanthrene : A pentacyclic ortho- and peri-fused polycyclic arene consisting of a dihydrocyclopenta[ij]tetraphene ring system with a methyl substituent at the 3-position.	1.97	1	0	ortho- and peri-fused polycyclic arene	aryl hydrocarbon receptor agonist; carcinogenic agent
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.	2.25	1	0	C-nitro compound	antimycobacterial drug; EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor; mycotoxin; neurotoxin
4-(2-aminoethyl)benzenesulfonylfluoride [no description available]	1.99	1	0
p-chloromercuribenzoic acid p-Chloromercuribenzoic Acid: An organic mercurial used as a sulfhydryl reagent.	1.99	1	0	chlorine molecular entity; mercuribenzoic acid
phenytoin [no description available]	1.95	1	0	imidazolidine-2,4-dione	anticonvulsant; drug allergen; sodium channel blocker; teratogenic agent
5-dimethylamiloride 5-dimethylamiloride: has anti-HIV-1 activity	1.99	1	0
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.	3.05	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.	2.31	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
8-phenyltheophylline 8-phenyltheophylline: purinergic P1 receptor antagonist	3.08	1	0
acebutolol Acebutolol: A cardioselective beta-1 adrenergic antagonist with little effect on the bronchial receptors. The drug has stabilizing and quinidine-like effects on cardiac rhythm, as well as weak inherent sympathomimetic action.. acebutolol : An ether that is the 2-acetyl-4-(butanoylamino)phenyl ether of the primary hydroxy group of 3-(propan-2-ylamino)propane-1,2-diol.	3.06	1	0	aromatic amide; ethanolamines; ether; monocarboxylic acid amide; propanolamine; secondary amino compound	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; sympathomimetic agent
alpha-cyano-4-hydroxycinnamate alpha-cyano-4-hydroxycinnamate: specific inhibitor of pyruvate transport in rat liver mitochondria & human erythrocytes; structure	2.68	3	0
amifostine anhydrous Amifostine: A phosphorothioate proposed as a radiation-protective agent. It causes splenic vasodilation and may block autonomic ganglia.. amifostine : An organic thiophosphate that is the S-phospho derivative of 2-[(3-aminopropyl)amino]ethanethiol. A prodrug for the free thiol, WR-1065, which is used as a cytoprotectant in cancer chemotherapy and radiotherapy.	2.04	1	0	diamine; organic thiophosphate	antioxidant; prodrug; radiation protective agent
aminoglutethimide Aminoglutethimide: An aromatase inhibitor that is used in the treatment of advanced BREAST CANCER.. aminoglutethimide : A dicarboximide that is a six-membered cyclic compound having ethyl and 4-aminophenyl substituents at the 3-position.	3.06	1	0	dicarboximide; piperidones; substituted aniline	adrenergic agent; anticonvulsant; antineoplastic agent; EC 1.14.14.14 (aromatase) 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.	1.95	1	0	N-acylglycine	Daphnia magna metabolite
theophylline [no description available]	5.37	4	1	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
amprolium Amprolium: A veterinary coccidiostat that interferes with THIAMINE metabolism.. amprolium : An organic chloride salt having 1-[(4-amino-2-propylpyrimidin-5-yl)methyl]-2-methylpyridin-1-ium as the counterion. Used for prevention of coccidiosis in poultry and cattle.. amprolium(1+) : A pyridinium ion that is the cationic portion of amprolium, a veterinary drug which is used for prevention of coccidiosis in poultry and cattle.	2.06	1	0	pyridinium ion	coccidiostat
arecoline Arecoline: An alkaloid obtained from the betel nut (Areca catechu), fruit of a palm tree. It is an agonist at both muscarinic and nicotinic acetylcholine receptors. It is used in the form of various salts as a ganglionic stimulant, a parasympathomimetic, and a vermifuge, especially in veterinary practice. It has been used as a euphoriant in the Pacific Islands.. arecoline : A tetrahydropyridine that is 1,2,5,6-tetrahydropyridine with a methyl group at position 1, and a methoxycarbonyl group at position 3. An alkaloid found in the areca nut, it acts as an agonist of muscarinic acetylcholine.	3.06	1	0	enoate ester; methyl ester; pyridine alkaloid; tetrahydropyridine	metabolite; muscarinic agonist
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.	3.35	6	0	benzoic acids; phenyl acetates; salicylates	anticoagulant; antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; EC 1.1.1.188 (prostaglandin-F synthase) inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; plant activator; platelet aggregation inhibitor; prostaglandin antagonist; teratogenic agent
benfluorex [no description available]	2.01	1	0	benzoate ester
benserazide Benserazide: An inhibitor of DOPA DECARBOXYLASE that does not enter the central nervous system. It is often given with LEVODOPA in the treatment of parkinsonism to prevent the conversion of levodopa to dopamine in the periphery, thereby increasing the amount that reaches the central nervous system and reducing the required dose. It has no antiparkinson actions when given alone.. benserazide : A carbohydrazide that results from the formal condensation of the carboxy group of DL-serine with the primary amino group of 4-(hydrazinylmethyl)benzene-1,2,3-triol. An aromatic-L-amino-acid decarboxylase inhibitor (DOPA decarboxylase inhibitor) that does not enter the central nervous system, it is used as its hydrochloride salt as an adjunct to levodopa in the treatment of parkinsonism. By preventing the conversion of levodopa to dopamine in the periphery, it causes an increase in the amount of levodopa reaching the central nervous system and so reduces the required dose. Benserazide has no antiparkinson actions when given alone.	1.96	1	0	carbohydrazide; catechols; primary alcohol; primary amino compound	antiparkinson drug; dopaminergic agent; EC 4.1.1.28 (aromatic-L-amino-acid decarboxylase) inhibitor
benzo(a)pyrene Benzo(a)pyrene: A potent mutagen and carcinogen. It is a public health concern because of its possible effects on industrial workers, as an environmental pollutant, an as a component of tobacco smoke.. benzo[a]pyrene : An ortho- and peri-fused polycyclic arene consisting of five fused benzene rings.	2.03	1	0	ortho- and peri-fused polycyclic arene	carcinogenic agent; mouse metabolite
benzothiazide benzothiazide: structure. benzthiazide : 7-Sulfamoyl-1,2,4-benzothiadiazine 1,1-dioxide in which the hydrogen at position 6 is substituted by chlorine and that at position 3 is substituted by a benzylsulfanylmethyl group. A diuretic, it is used to treat hypertension and edema.	2.02	1	0	benzothiadiazine; sulfonamide	antihypertensive agent; diuretic
beta-naphthoflavone beta-Naphthoflavone: A polyaromatic hydrocarbon inducer of P4501A1 and P4501A2 cytochromes. (Proc Soc Exp Biol Med 1994 Dec:207(3):302-308). beta-naphthoflavone : An extended flavonoid resulting from the formal fusion of a benzene ring with the f side of flavone.	2.03	1	0	extended flavonoid; naphtho-gamma-pyrone; organic heterotricyclic compound	aryl hydrocarbon receptor agonist
1-o-hexadecyl-2-n-methylcarbamylphosphatidylcholine 1-O-hexadecyl-2-N-methylcarbamylphosphatidylcholine: biologically active analog of PAF; structure given in first source	2.02	1	0
caffeine [no description available]	6.08	5	1	purine alkaloid; trimethylxanthine	adenosine A2A receptor antagonist; adenosine receptor antagonist; adjuvant; central nervous system stimulant; diuretic; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; environmental contaminant; food additive; fungal metabolite; geroprotector; human blood serum metabolite; mouse metabolite; mutagen; plant metabolite; psychotropic drug; ryanodine receptor agonist; xenobiotic
verapamil Verapamil: A calcium channel blocker that is a class IV anti-arrhythmia agent.. verapamil : A racemate comprising equimolar amounts of dexverapamil and (S)-verapamil. An L-type calcium channel blocker of the phenylalkylamine class, it is used (particularly as the hydrochloride salt) in the treatment of hypertension, angina pectoris and cardiac arrhythmia, and as a preventive medication for migraine.. 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile : A tertiary amino compound that is 3,4-dimethoxyphenylethylamine in which the hydrogens attached to the nitrogen are replaced by a methyl group and a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.	2.39	2	0	aromatic ether; nitrile; polyether; tertiary amino compound
camphor, (+-)-isomer [no description available]	2.4	2	0	bornane monoterpenoid; cyclic monoterpene ketone	plant metabolite
cetyl alcohol cetyl alcohol: has been used for eczema, skin irritations; RN given refers to parent cpd; structure. hexadecanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of sixteen carbon atoms.. hexadecan-1-ol : A long-chain primary fatty alcohol that is hexadecane substituted by a hydroxy group at position 1.	3.25	1	0	hexadecanol; long-chain primary fatty alcohol	algal metabolite; flavouring agent; human metabolite; plant metabolite
chloral hydrate [no description available]	1.95	1	0	aldehyde hydrate; ethanediol; organochlorine compound	general anaesthetic; mouse metabolite; sedative; xenobiotic
chlorpyrifos Chlorpyrifos: An organothiophosphate cholinesterase inhibitor that is used as an insecticide and as an acaricide.. chlorpyrifos : An organic thiophosphate that is O,O-diethyl hydrogen phosphorothioate in which the hydrogen of the hydroxy group has been replaced by a 3,5,6-trichloropyridin-2-yl group.	2.02	1	0	chloropyridine; organic thiophosphate	acaricide; agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; environmental contaminant; insecticide; xenobiotic
clofazimine Clofazimine: A fat-soluble riminophenazine dye used for the treatment of leprosy. It has been used investigationally in combination with other antimycobacterial drugs to treat Mycobacterium avium infections in AIDS patients. Clofazimine also has a marked anti-inflammatory effect and is given to control the leprosy reaction, erythema nodosum leprosum. (From AMA Drug Evaluations Annual, 1993, p1619). clofazimine : 3-Isopropylimino-3,5-dihydro-phenazine in which the hydrogen at position 5 is substituted substituted by a 4-chlorophenyl group, and that at position 2 is substituted by a (4-chlorophenyl)amino group. A dark red crystalline solid, clofazimine is an antimycobacterial and is one of the main drugs used for the treatment of multi-bacillary leprosy. However, it can cause red/brown discolouration of the skin, so other treatments are often preferred in light-skinned patients.	1.97	1	0	monochlorobenzenes; phenazines	dye; leprostatic drug; non-steroidal anti-inflammatory drug
clofibrate angiokapsul: contains clofibrate & insoitolnicotinate	4.74	7	1	aromatic ether; ethyl ester; monochlorobenzenes	anticholesteremic drug; antilipemic drug; geroprotector; PPARalpha agonist
cystamine [no description available]	1.95	1	0	organic disulfide; primary amino compound	EC 2.3.2.13 (protein-glutamine gamma-glutamyltransferase) inhibitor
dapsone [no description available]	3.47	2	0	substituted aniline; sulfone	anti-inflammatory drug; antiinfective agent; antimalarial; leprostatic drug
deferoxamine Deferoxamine: Natural product isolated from Streptomyces pilosus. It forms iron complexes and is used as a chelating agent, particularly in the mesylate form.. desferrioxamine B : An acyclic desferrioxamine that is butanedioic acid in which one of the carboxy groups undergoes formal condensation with the primary amino group of N-(5-aminopentyl)-N-hydroxyacetamide and the second carboxy group undergoes formal condensation with the hydroxyamino group of N(1)-(5-aminopentyl)-N(1)-hydroxy-N(4)-[5-(hydroxyamino)pentyl]butanediamide. It is a siderophore native to Streptomyces pilosus biosynthesised by the DesABCD enzyme cluster as a high affinity Fe(III) chelator.	2.41	1	0	acyclic desferrioxamine	bacterial metabolite; ferroptosis inhibitor; iron chelator; siderophore
eflornithine Eflornithine: An inhibitor of ORNITHINE DECARBOXYLASE, the rate limiting enzyme of the polyamine biosynthetic pathway.. eflornithine : A fluoroamino acid that is ornithine substituted by a difluoromethyl group at position 2.	2.02	1	0	alpha-amino acid; fluoroamino acid	trypanocidal drug
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.	2.88	4	0	acyclic carboxylic anhydride
diflunisal Diflunisal: A salicylate derivative and anti-inflammatory analgesic with actions and side effects similar to those of ASPIRIN.. diflunisal : An organofluorine compound comprising salicylic acid having a 2,4-difluorophenyl group at the 5-position.	2.13	1	0	monohydroxybenzoic acid; organofluorine compound	non-narcotic analgesic; non-steroidal anti-inflammatory drug
disulfiram [no description available]	1.95	1	0	organic disulfide; organosulfur acaricide	angiogenesis inhibitor; antineoplastic agent; apoptosis inducer; EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor; EC 3.1.1.1 (carboxylesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 5.99.1.2 (DNA topoisomerase) inhibitor; ferroptosis inducer; fungicide; NF-kappaB inhibitor
valproic acid Valproic Acid: A fatty acid with anticonvulsant and anti-manic properties that is used in the treatment of EPILEPSY and BIPOLAR DISORDER. The mechanisms of its therapeutic actions are not well understood. It may act by increasing GAMMA-AMINOBUTYRIC ACID levels in the brain or by altering the properties of VOLTAGE-GATED SODIUM CHANNELS.. valproic acid : A branched-chain saturated fatty acid that comprises of a propyl substituent on a pentanoic acid stem.	4.59	8	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
ellipticine ellipticine : A organic heterotetracyclic compound that is pyrido[4,3-b]carbazole carrying two methyl substituents at positions 5 and 11.	1.96	1	0	indole alkaloid; organic heterotetracyclic compound; organonitrogen heterocyclic compound; polycyclic heteroarene	antineoplastic agent; plant metabolite
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.	2.64	3	0	aromatic ether; hydrazone; nitrile; organofluorine compound	ATP synthase inhibitor; geroprotector; ionophore
fenfluramine Fenfluramine: A centrally active drug that apparently both blocks serotonin uptake and provokes transport-mediated serotonin release.. fenfluramine : A secondary amino compound that is 1-phenyl-propan-2-amine in which one of the meta-hydrogens is substituted by trifluoromethyl, and one of the hydrogens attached to the nitrogen is substituted by an ethyl group. It binds to the serotonin reuptake pump, causing inhbition of serotonin uptake and release of serotonin. The resulting increased levels of serotonin lead to greater serotonin receptor activation which in turn lead to enhancement of serotoninergic transmission in the centres of feeding behavior located in the hypothalamus. This suppresses the appetite for carbohydrates. Fenfluramine was used as the hydrochloride for treatment of diabetes and obesity. It was withdrawn worldwide after reports of heart valve disease and pulmonary hypertension.	2.38	2	0	(trifluoromethyl)benzenes; secondary amino compound	appetite depressant; serotonergic agonist; serotonin uptake inhibitor
fluconazole Fluconazole: Triazole antifungal agent that is used to treat oropharyngeal CANDIDIASIS and cryptococcal MENINGITIS in AIDS.. fluconazole : A member of the class of triazoles that is propan-2-ol substituted at position 1 and 3 by 1H-1,2,4-triazol-1-yl groups and at position 2 by a 2,4-difluorophenyl group. It is an antifungal drug used for the treatment of mucosal candidiasis and for systemic infections including systemic candidiasis, coccidioidomycosis, and cryptococcosis.	2.41	1	0	conazole antifungal drug; difluorobenzene; tertiary alcohol; triazole antifungal drug	environmental contaminant; P450 inhibitor; xenobiotic
fusaric acid Fusaric Acid: A picolinic acid derivative isolated from various Fusarium species. It has been proposed for a variety of therapeutic applications but is primarily used as a research tool. Its mechanisms of action are poorly understood. It probably inhibits DOPAMINE BETA-HYDROXYLASE, the enzyme that converts dopamine to norepinephrine. It may also have other actions, including the inhibition of cell proliferation and DNA synthesis.	1.96	1	0	aromatic carboxylic acid; pyridines
gemfibrozil [no description available]	1.97	1	0	aromatic ether	antilipemic drug
gentamicin Gentamicins: A complex of closely related aminoglycosides obtained from MICROMONOSPORA purpurea and related species. They are broad-spectrum antibiotics, but may cause ear and kidney damage. They act to inhibit PROTEIN BIOSYNTHESIS.	3.45	8	0
2,5-dihydroxybenzoic acid 2,5-dihydroxybenzoic acid: RN given refers to parent cpd; a oxidative product of saligenin. 2,5-dihydroxybenzoic acid : A dihydroxybenzoic acid having the two hydroxy groups at the 2- and 5-positions.	2.15	1	0	dihydroxybenzoic acid	EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; fungal metabolite; human metabolite; MALDI matrix material; mouse metabolite
glipizide Glipizide: An oral hypoglycemic agent which is rapidly absorbed and completely metabolized.. glipizide : An N-sulfonylurea that is glyburide in which the (5-chloro-2-methoxybenzoyl group is replaced by a (5-methylpyrazin-2-yl)carbonyl group. An oral hypoglycemic agent, it is used in the treatment of type 2 diabetes mellitus.	2.13	1	0	aromatic amide; monocarboxylic acid amide; N-sulfonylurea; pyrazines	EC 2.7.1.33 (pantothenate kinase) inhibitor; hypoglycemic agent; insulin secretagogue
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.	1.97	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
guanidine Guanidine: A strong organic base existing primarily as guanidium ions at physiological pH. It is found in the urine as a normal product of protein metabolism. It is also used in laboratory research as a protein denaturant. (From Martindale, the Extra Pharmacopoeia, 30th ed and Merck Index, 12th ed) It is also used in the treatment of myasthenia and as a fluorescent probe in HPLC.. guanidine : An aminocarboxamidine, the parent compound of the guanidines.	2.7	3	0	carboxamidine; guanidines; one-carbon compound
halothane [no description available]	1.96	1	0	haloalkane; organobromine compound; organochlorine compound; organofluorine compound	inhalation anaesthetic
ibuprofen Midol: combination of cinnamedrine, phenacetin, aspirin & caffeine	2.1	1	0	monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; radical scavenger; xenobiotic
phenelzine Phenelzine: One of the MONOAMINE OXIDASE INHIBITORS used to treat DEPRESSION; PHOBIC DISORDERS; and PANIC.	1.95	1	0	primary amine
iodoacetamide [no description available]	4.27	19	0
indolepropionic acid indolepropionic acid: structure in third source. 3-(1H-indol-3-yl)propanoic acid : An indol-3-yl carboxylic acid that is propionic acid substituted by a 1H-indol-3-yl group at position 3.	1.99	1	0	indol-3-yl carboxylic acid	auxin; human metabolite; plant metabolite
isoflurane Isoflurane: A stable, non-explosive inhalation anesthetic, relatively free from significant side effects.	1.99	1	0	organofluorine compound	inhalation anaesthetic
isoniazid Hydra: A genus of freshwater polyps in the family Hydridae, order Hydroida, class HYDROZOA. They are of special interest because of their complex organization and because their adult organization corresponds roughly to the gastrula of higher animals.. hydrazide : Compounds derived from oxoacids RkE(=O)l(OH)m (l =/= 0) by replacing -OH by -NRNR2 (R groups are commonly H). (IUPAC).	3.76	3	0	carbohydrazide	antitubercular agent; drug allergen
2-propanol 2-Propanol: An isomer of 1-PROPANOL. It is a colorless liquid having disinfectant properties. It is used in the manufacture of acetone and its derivatives and as a solvent. Topically, it is used as an antiseptic.. propan-2-ol : A secondary alcohol that is propane in which one of the hydrogens attached to the central carbon is substituted by a hydroxy group.	4.69	8	0	secondary alcohol; secondary fatty alcohol	protic solvent
isoproterenol Isoproterenol: Isopropyl analog of EPINEPHRINE; beta-sympathomimetic that acts on the heart, bronchi, skeletal muscle, alimentary tract, etc. It is used mainly as bronchodilator and heart stimulant.. isoprenaline : A secondary amino compound that is noradrenaline in which one of the hydrogens attached to the nitrogen is replaced by an isopropyl group. A sympathomimetic acting almost exclusively on beta-adrenergic receptors, it is used (mainly as the hydrochloride salt) as a bronghodilator and heart stimulant for the management of a variety of cardiac disorders.	2.69	3	0	catechols; secondary alcohol; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; cardiotonic drug; sympathomimetic agent
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.	3.04	1	0	monohydroxyquinoline; quinolinemonocarboxylic acid	G-protein-coupled receptor agonist; human metabolite; neuroprotective agent; nicotinic antagonist; NMDA receptor antagonist; Saccharomyces cerevisiae metabolite
benzylsuccinic acid benzylsuccinic acid: inhibitor of carboxypeptidase A. 2-benzylsuccinic acid : A dicarboxylic acid consisting of succinic acid carrying a 2-benzyl substituent.	1.96	1	0	dicarboxylic acid	bacterial xenobiotic metabolite
mimosine Mimosine: 3-Hydroxy-4-oxo-1(4H)-pyridinealanine. An antineoplastic alanine-substituted pyridine derivative isolated from Leucena glauca.	2	1	0	alpha-amino acid
2-phenylglycine 2-phenylglycine: RN given refers to cpd without isomeric designation; structure. alpha-phenylglycine : An amino acid with a structure in which a phenyl ring is bonded to the alpha-carbon of glycine.	2.51	2	0	non-proteinogenic alpha-amino acid	human metabolite
malathion Malathion: A wide spectrum aliphatic organophosphate insecticide widely used for both domestic and commercial agricultural purposes.. malathion : A racemate comprising equimolar amounts of (R) and (S)-malathion. It is a broad spectrum organophosphate proinsecticide used to control a wide range of pests including Coleoptera, Diptera, fruit flies, mosquitos and spider mites.. diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate : A diester that is diethyl succinate in which position 2 is substituted by a (dimethoxyphosphorothioyl)thio group.	1.94	1	0	diester; ethyl ester; organic thiophosphate
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.	2.03	1	0	amino acid; aromatic amine; monocarboxylic acid; monohydroxybenzoic acid; phenols	non-steroidal anti-inflammatory drug
mescaline Mescaline: Hallucinogenic alkaloid isolated from the flowering heads (peyote) of Lophophora (formerly Anhalonium) williamsii, a Mexican cactus used in Indian religious rites and as an experimental psychotomimetic. Among its cellular effects are agonist actions at some types of serotonin receptors. It has no accepted therapeutic uses although it is legal for religious use by members of the Native American Church.. mescaline : A phenethylamine alkaloid that is phenethylamine substituted at positions 3, 4 and 5 by methoxy groups.	1.95	1	0	methoxybenzenes; phenethylamine alkaloid; primary amino compound	hallucinogen
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.	2.75	3	0	guanidines	environmental contaminant; geroprotector; hypoglycemic agent; xenobiotic
nocodazole [no description available]	2	1	0	aromatic ketone; benzimidazoles; carbamate ester; thiophenes	antimitotic; antineoplastic agent; microtubule-destabilising agent; tubulin modulator
methyl methanesulfonate [no description available]	2.37	2	0	methanesulfonate ester	alkylating agent; apoptosis inducer; carcinogenic agent; genotoxin; mutagen
metronidazole Metronidazole: A nitroimidazole used to treat AMEBIASIS; VAGINITIS; TRICHOMONAS INFECTIONS; GIARDIASIS; ANAEROBIC BACTERIA; and TREPONEMAL INFECTIONS.. metronidazole : A member of the class of imidazoles substituted at C-1, -2 and -5 with 2-hydroxyethyl, nitro and methyl groups respectively. It has activity against anaerobic bacteria and protozoa, and has a radiosensitising effect on hypoxic tumour cells. It may be given by mouth in tablets, or as the benzoate in an oral suspension. The hydrochloride salt can be used in intravenous infusions. Metronidazole is a prodrug and is selective for anaerobic bacteria due to their ability to intracellularly reduce the nitro group of metronidazole to give nitroso-containing intermediates. These can covalently bind to DNA, disrupting its helical structure, inducing DNA strand breaks and inhibiting bacterial nucleic acid synthesis, ultimately resulting in bacterial cell death.	1.97	1	0	C-nitro compound; imidazoles; primary alcohol	antiamoebic agent; antibacterial drug; antimicrobial agent; antiparasitic agent; antitrichomonal drug; environmental contaminant; prodrug; radiosensitizing agent; xenobiotic
molsidomine Molsidomine: A morpholinyl sydnone imine ethyl ester, having a nitrogen in place of the keto oxygen. It acts as NITRIC OXIDE DONORS and is a vasodilator that has been used in ANGINA PECTORIS.. molsidomine : A member of the class of oxadiazoles that is 1,2,3-oxadiazole substituted by morpholin-4-yl and (ethoxycarbonyl)azanidyl groups at positions 3 and 5, respectively. It is used as a vasodilator drug for the treatment of myocardial ischemic syndrome and congestive heart failure.	2.02	1	0	ethyl ester; morpholines; oxadiazole; zwitterion	antioxidant; apoptosis inhibitor; cardioprotective agent; nitric oxide donor; vasodilator agent
n-bromoacetamide [no description available]	2.02	1	0
ethylmaleimide Ethylmaleimide: A sulfhydryl reagent that is widely used in experimental biochemical studies.	5.19	16	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
neostigmine Neostigmine: A cholinesterase inhibitor used in the treatment of myasthenia gravis and to reverse the effects of muscle relaxants such as gallamine and tubocurarine. Neostigmine, unlike PHYSOSTIGMINE, does not cross the blood-brain barrier.. neostigmine : A quaternary ammonium ion comprising an anilinium ion core having three methyl substituents on the aniline nitrogen, and a 3-[(dimethylcarbamoyl)oxy] substituent at position 3. It is a parasympathomimetic which acts as a reversible acetylcholinesterase inhibitor.	1.95	1	0	quaternary ammonium ion	antidote to curare poisoning; EC 3.1.1.7 (acetylcholinesterase) inhibitor
netropsin Netropsin: A basic polypeptide isolated from Streptomyces netropsis. It is cytotoxic and its strong, specific binding to A-T areas of DNA is useful to genetics research.	2.05	1	0
octopamine Octopamine: An alpha-adrenergic sympathomimetic amine, biosynthesized from tyramine in the CNS and platelets and also in invertebrate nervous systems. It is used to treat hypotension and as a cardiotonic. The natural D(-) form is more potent than the L(+) form in producing cardiovascular adrenergic responses. It is also a neurotransmitter in some invertebrates.. octopamine : A member of the class of phenylethanolamines that is phenol which is substituted at the para- position by a 2-amino-1-hydroxyethyl group. A biogenic phenylethanolamine which has been found to act as a neurotransmitter, neurohormone or neuromodulator in invertebrates.	2.37	2	0	phenylethanolamines; tyramines	neurotransmitter
aminosalicylic acid Aminosalicylic Acid: An antitubercular agent often administered in association with ISONIAZID. The sodium salt of the drug is better tolerated than the free acid.. 4-aminosalicylic acid : An aminobenzoic acid that is salicylic acid substituted by an amino group at position 4.	3.47	2	0	aminobenzoic acid; phenols	antitubercular agent
quinone benzoquinone : The simplest members of the class of benzoquinones, consisting of cyclohexadiene which is substituted by two oxo groups.. 1,4-benzoquinone : The simplest member of the class of 1,4-benzoquinones, obtained by the formal oxidation of hydroquinone to the corresponding diketone. It is a metabolite of benzene.. quinone : Compounds having a fully conjugated cyclic dione structure, such as that of benzoquinones, derived from aromatic compounds by conversion of an even number of -CH= groups into -C(=O)- groups with any necessary rearrangement of double bonds (polycyclic and heterocyclic analogues are included).	1.98	1	0	1,4-benzoquinones	cofactor; human xenobiotic metabolite; mouse metabolite
fenclonine Fenclonine: A selective and irreversible inhibitor of tryptophan hydroxylase, a rate-limiting enzyme in the biosynthesis of serotonin (5-HYDROXYTRYPTAMINE). Fenclonine acts pharmacologically to deplete endogenous levels of serotonin.	1.96	1	0	phenylalanine derivative
patulin Patulin: 4-Hydroxy-4H-furo(3,2-c)pyran-2(6H)-one. A mycotoxin produced by several species of Aspergillus and Penicillium. It is found in unfermented apple and grape juice and field crops. It has antibiotic properties and has been shown to be carcinogenic and mutagenic and causes chromosome damage in biological systems.. patulin : A furopyran and lactone that is (2H-pyran-3(6H)-ylidene)acetic acid which is substituted by hydroxy groups at positions 2 and 4 and in which the hydroxy group at position 4 has condensed with the carboxy group to give the corresponding bicyclic lactone. A mycotoxin produced by several species of Aspergillus and Penicillium, it has antibiotic properties but has been shown to be carcinogenic and mutagenic.	2.35	2	0	furopyran; gamma-lactone; lactol	antimicrobial agent; Aspergillus metabolite; carcinogenic agent; mutagen; mycotoxin; Penicillium metabolite
pentobarbital Pentobarbital: A short-acting barbiturate that is effective as a sedative and hypnotic (but not as an anti-anxiety) agent and is usually given orally. It is prescribed more frequently for sleep induction than for sedation but, like similar agents, may lose its effectiveness by the second week of continued administration. (From AMA Drug Evaluations Annual, 1994, p236). pentobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and sec-pentyl groups.	1.95	1	0	barbiturates	GABAA receptor agonist
phenobarbital Phenobarbital: A barbituric acid derivative that acts as a nonselective central nervous system depressant. It potentiates GAMMA-AMINOBUTYRIC ACID action on GABA-A RECEPTORS, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations.. phenobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and phenyl groups.	3.06	1	0	barbiturates	anticonvulsant; drug allergen; excitatory amino acid antagonist; sedative
oxophenylarsine oxophenylarsine: inhibits protein-tyrosine-phosphatase. phenylarsine oxide : An arsine oxide derived from phenylarsine.	1.98	1	0	arsine oxides	antineoplastic agent; apoptosis inducer; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor
phenylmethylsulfonyl fluoride Phenylmethylsulfonyl Fluoride: An enzyme inhibitor that inactivates IRC-50 arvin, subtilisin, and the fatty acid synthetase complex.. phenylmethanesulfonyl fluoride : An acyl fluoride with phenylmethanesulfonyl as the acyl group.	2.65	3	0	acyl fluoride	serine proteinase inhibitor
o-phthalaldehyde o-Phthalaldehyde: A reagent that forms fluorescent conjugation products with primary amines. It is used for the detection of many biogenic amines, peptides, and proteins in nanogram quantities in body fluids.. phthalaldehyde : A dialdehyde in which two formyl groups are attached to adjacent carbon centres on a benzene ring.	2.02	1	0	benzaldehydes; dialdehyde	epitope
pirenzepine Pirenzepine: An antimuscarinic agent that inhibits gastric secretion at lower doses than are required to affect gastrointestinal motility, salivary, central nervous system, cardiovascular, ocular, and urinary function. It promotes the healing of duodenal ulcers and due to its cytoprotective action is beneficial in the prevention of duodenal ulcer recurrence. It also potentiates the effect of other antiulcer agents such as CIMETIDINE and RANITIDINE. It is generally well tolerated by patients.	2.02	1	0	pyridobenzodiazepine	anti-ulcer drug; antispasmodic drug; muscarinic antagonist
potassium chloride Potassium Chloride: A white crystal or crystalline powder used in BUFFERS; FERTILIZERS; and EXPLOSIVES. It can be used to replenish ELECTROLYTES and restore WATER-ELECTROLYTE BALANCE in treating HYPOKALEMIA.. potassium chloride : A metal chloride salt with a K(+) counterion.	3.97	14	0	inorganic chloride; inorganic potassium salt; potassium salt	fertilizer
procainamide Procainamide: A class Ia antiarrhythmic drug that is structurally-related to PROCAINE.. procainamide : A benzamide that is 4-aminobenzamide substituted on the amide N by a 2-(diethylamino)ethyl group. It is a pharmaceutical antiarrhythmic agent used for the medical treatment of cardiac arrhythmias.	4.16	5	0	benzamides	anti-arrhythmia drug; platelet aggregation inhibitor; sodium channel blocker
propofol Propofol: An intravenous anesthetic agent which has the advantage of a very rapid onset after infusion or bolus injection plus a very short recovery period of a couple of minutes. (From Smith and Reynard, Textbook of Pharmacology, 1992, 1st ed, p206). Propofol has been used as ANTICONVULSANTS and ANTIEMETICS.. propofol : A phenol resulting from the formal substitution of the hydrogen at the 2 position of 1,3-diisopropylbenzene by a hydroxy group.	2.41	1	0	phenols	anticonvulsant; antiemetic; intravenous anaesthetic; radical scavenger; sedative
propranolol Propranolol: A widely used non-cardioselective beta-adrenergic antagonist. Propranolol has been used for MYOCARDIAL INFARCTION; ARRHYTHMIA; ANGINA PECTORIS; HYPERTENSION; HYPERTHYROIDISM; MIGRAINE; PHEOCHROMOCYTOMA; and ANXIETY but adverse effects instigate replacement by newer drugs.. propranolol : A propanolamine that is propan-2-ol substituted by a propan-2-ylamino group at position 1 and a naphthalen-1-yloxy group at position 3.	1.96	1	0	naphthalenes; propanolamine; secondary amine	anti-arrhythmia drug; antihypertensive agent; anxiolytic drug; beta-adrenergic antagonist; environmental contaminant; human blood serum metabolite; vasodilator agent; xenobiotic
sebacic acid sebacic acid : An alpha,omega-dicarboxylic acid that is the 1,8-dicarboxy derivative of octane.	1.96	1	0	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	human metabolite; plant metabolite
linsidomine linsidomine: RN given refers to parent cpd; structure	2.02	1	0	morpholines
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.	2.35	2	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.	2.38	2	0	haloacetic acid; organoiodine compound	alkylating agent
stearic acid octadecanoic acid : A C18 straight-chain saturated fatty acid component of many animal and vegetable lipids. As well as in the diet, it is used in hardening soaps, softening plastics and in making cosmetics, candles and plastics.	2.08	1	0	long-chain fatty acid; saturated fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; human metabolite; plant metabolite
sulfamethazine Sulfamethazine: A sulfanilamide anti-infective agent. It has a spectrum of antimicrobial action similar to other sulfonamides.. sulfamethazine : A sulfonamide consisting of pyrimidine with methyl substituents at the 4- and 6-positions and a 4-aminobenzenesulfonamido group at the 2-position.	2.89	4	0	pyrimidines; sulfonamide antibiotic; sulfonamide	antibacterial drug; antiinfective agent; antimicrobial agent; carcinogenic agent; drug allergen; EC 2.5.1.15 (dihydropteroate synthase) inhibitor; environmental contaminant; ligand; xenobiotic
sulfamethoxazole Sulfamethoxazole: A bacteriostatic antibacterial agent that interferes with folic acid synthesis in susceptible bacteria. Its broad spectrum of activity has been limited by the development of resistance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p208). sulfamethoxazole : An isoxazole (1,2-oxazole) compound having a methyl substituent at the 5-position and a 4-aminobenzenesulfonamido group at the 3-position.	3.23	6	0	isoxazoles; substituted aniline; sulfonamide antibiotic; sulfonamide	antibacterial agent; antiinfective agent; antimicrobial agent; drug allergen; EC 1.1.1.153 [sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming)] inhibitor; EC 2.5.1.15 (dihydropteroate synthase) inhibitor; environmental contaminant; epitope; P450 inhibitor; xenobiotic
sulfasalazine Sulfasalazine: A drug that is used in the management of inflammatory bowel diseases. Its activity is generally considered to lie in its metabolic breakdown product, 5-aminosalicylic acid (see MESALAMINE) released in the colon. (From Martindale, The Extra Pharmacopoeia, 30th ed, p907). sulfasalazine : An azobenzene consisting of diphenyldiazene having a carboxy substituent at the 4-position, a hydroxy substituent at the 3-position and a 2-pyridylaminosulphonyl substituent at the 4'-position.	3.06	1	0
sulfathiazole Sulfathiazole: A sulfathiazole compound that is used as a short-acting anti-infective agent. It is no longer commonly used systemically due to its toxicity, but may still be applied topically in combination with other drugs for the treatment of vaginal and skin infections, and is still used in veterinary medicine.. sulfathiazole : A 1,3-thiazole compound having a 4-aminobenzenesulfonamido group at the 2-position.	3.06	1	0	1,3-thiazoles; substituted aniline; sulfonamide antibiotic; sulfonamide	antiinfective agent; drug allergen; EC 2.5.1.15 (dihydropteroate synthase) inhibitor; environmental contaminant; xenobiotic
suramin Suramin: A polyanionic compound with an unknown mechanism of action. It is used parenterally in the treatment of African trypanosomiasis and it has been used clinically with diethylcarbamazine to kill the adult Onchocerca. (From AMA Drug Evaluations Annual, 1992, p1643) It has also been shown to have potent antineoplastic properties.. suramin : A member of the class of phenylureas that is urea in which each of the amino groups has been substituted by a 3-({2-methyl-5-[(4,6,8-trisulfo-1-naphthyl)carbamoyl]phenyl}carbamoyl)phenyl group. An activator of both the rabbit skeletal muscle RyR1 and sheep cardiac RyR2 isoform ryanodine receptor channels, it has been used for the treatment of human African trypanosomiasis for over 100 years.	1.96	1	0	naphthalenesulfonic acid; phenylureas; secondary carboxamide	angiogenesis inhibitor; antinematodal drug; antineoplastic agent; apoptosis inhibitor; EC 2.7.11.13 (protein kinase C) inhibitor; GABA antagonist; GABA-gated chloride channel antagonist; purinergic receptor P2 antagonist; ryanodine receptor agonist; trypanocidal drug
2,4-thiazolidinedione thiazolidine-2,4-dione: structure in first source. 1,3-thiazolidine-2,4-dione : A thiazolidenedione carrying oxo substituents at positions 2 and 4.	2.05	1	0	thiazolidenedione
tilorone Tilorone: An antiviral agent used as its hydrochloride. It is the first recognized synthetic, low-molecular-weight compound that is an orally active interferon inducer, and is also reported to have antineoplastic and anti-inflammatory actions.. tilorone : A member of the class of fluoren-9-ones that is 9H-fluoren-9-one which is substituted by a 2-(diethylamino)ethoxy group at positions 2 and 7. It is an interferon inducer and a selective alpha7 nicotinic acetylcholine receptor (alpha7 nAChR) agonist. Its hydrochloride salt is used as an antiviral drug.	6.98	1	0	aromatic ether; diether; fluoren-9-ones; tertiary amino compound	anti-inflammatory agent; antineoplastic agent; antiviral agent; interferon inducer; nicotinic acetylcholine receptor agonist
tolbutamide Tolbutamide: A sulphonylurea hypoglycemic agent with actions and uses similar to those of CHLORPROPAMIDE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p290). tolbutamide : An N-sulfonylurea that consists of 1-butylurea having a tosyl group attached at the 3-position.	7.65	3	0	N-sulfonylurea	human metabolite; hypoglycemic agent; insulin secretagogue; potassium channel blocker
tolmetin Tolmetin: A non-steroidal anti-inflammatory agent (ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL) similar in mode of action to INDOMETHACIN.. tolmetin : A monocarboxylic acid that is (1-methylpyrrol-2-yl)acetic acid substituted at position 5 on the pyrrole ring by a 4-methylbenzoyl group. Used in the form of its sodium salt dihydrate as a nonselective nonsteroidal anti-inflammatory drug.	2.02	1	0	aromatic ketone; monocarboxylic acid; pyrroles	EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-steroidal anti-inflammatory drug
triacetin Triacetin: A triglyceride that is used as an antifungal agent.. triacetin : A triglyceride obtained by acetylation of the three hydroxy groups of glycerol. It has fungistatic properties (based on release of acetic acid) and has been used in the topical treatment of minor dermatophyte infections.	2.05	1	0	triglyceride	adjuvant; antifungal drug; food additive carrier; food emulsifier; food humectant; fuel additive; plant metabolite; solvent
thenoyltrifluoroacetone Thenoyltrifluoroacetone: Chelating agent and inhibitor of cellular respiration.	2.06	1	0
tyramine [no description available]	2.91	4	0	monoamine molecular messenger; primary amino compound; tyramines	EC 3.1.1.8 (cholinesterase) inhibitor; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter
vesamicol vesamicol: RN given refers to parent cpd; structure	1.99	1	0	piperidines
3-(5'-hydroxymethyl-2'-furyl)-1-benzylindazole 3-(5'-hydroxymethyl-2'-furyl)-1-benzylindazole: antineoplastic; activates platelet guanylate cyclase; a radiosensitizing agent and guanylate cyclase activator; structure in first source. lificiguat : A member of the class of indazoles that is 1H-indazole which is substituted by a benzyl group at position 1 and a 5-(hydroxymethyl)-2-furyl group at position 3. It is an activator of soluble guanylate cyclase and inhibits platelet aggregation.	2.15	1	0	aromatic primary alcohol; furans; indazoles	antineoplastic agent; apoptosis inducer; platelet aggregation inhibitor; soluble guanylate cyclase activator; vasodilator agent
zomepirac zomepirac: RN given refers to parent cpd; structure	2.02	1	0	aromatic ketone; monocarboxylic acid; monochlorobenzenes; pyrroles	cardiovascular drug; non-steroidal anti-inflammatory drug
corticosterone [no description available]	2.39	2	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
sorbitol D-glucitol : The D-enantiomer of glucitol (also known as D-sorbitol).	1.95	1	0	glucitol	cathartic; Escherichia coli metabolite; food humectant; human metabolite; laxative; metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite; sweetening agent
alloxan Alloxan: Acidic compound formed by oxidation of URIC ACID. It is isolated as an efflorescent crystalline hydrate.. alloxan : A member of the class of pyrimidones, the structure of which is that of perhydropyrimidine substituted at C-2, -4, -5 and -6 by oxo groups.	1.93	1	0	pyrimidone	hyperglycemic agent; metabolite
2-aminophenol [no description available]	1.98	1	0	aminophenol	bacterial metabolite
thyroxine Thyroxine: The major hormone derived from the thyroid gland. Thyroxine is synthesized via the iodination of tyrosines (MONOIODOTYROSINE) and the coupling of iodotyrosines (DIIODOTYROSINE) in the THYROGLOBULIN. Thyroxine is released from thyroglobulin by proteolysis and secreted into the blood. Thyroxine is peripherally deiodinated to form TRIIODOTHYRONINE which exerts a broad spectrum of stimulatory effects on cell metabolism.. thyroxine : An iodothyronine compound having iodo substituents at the 3-, 3'-, 5- and 5'-positions.	2.65	3	0	2-halophenol; iodophenol; L-phenylalanine derivative; non-proteinogenic L-alpha-amino acid; thyroxine zwitterion; thyroxine	antithyroid drug; human metabolite; mouse metabolite; thyroid hormone
carbachol Carbachol: A slowly hydrolyzed CHOLINERGIC AGONIST that acts at both MUSCARINIC RECEPTORS and NICOTINIC RECEPTORS.	1.95	1	0	ammonium salt; carbamate ester	cardiotonic drug; miotic; muscarinic agonist; nicotinic acetylcholine receptor agonist; non-narcotic analgesic
aldosterone [no description available]	2.65	3	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
dehydroepiandrosterone Dehydroepiandrosterone: A major C19 steroid produced by the ADRENAL CORTEX. It is also produced in small quantities in the TESTIS and the OVARY. Dehydroepiandrosterone (DHEA) can be converted to TESTOSTERONE; ANDROSTENEDIONE; ESTRADIOL; and ESTRONE. Most of DHEA is sulfated (DEHYDROEPIANDROSTERONE SULFATE) before secretion.. dehydroepiandrosterone : An androstanoid that is androst-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 17. It is a naturally occurring steroid hormone produced by the adrenal glands.	2.4	2	0	17-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; androstanoid	androgen; human metabolite; mouse metabolite
n-hydroxy-2-aminofluorene N-hydroxy-2-aminofluorene: structure	7.88	4	0
hydroxyacetylaminofluorene Hydroxyacetylaminofluorene: A N-hydroxylated derivative of 2-ACETYLAMINOFLUORENE that has demonstrated carcinogenic action.	2.89	4	0	2-acetamidofluorenes
2-acetylaminofluorene 2-Acetylaminofluorene: A hepatic carcinogen whose mechanism of activation involves N-hydroxylation to the aryl hydroxamic acid followed by enzymatic sulfonation to sulfoxyfluorenylacetamide. It is used to study the carcinogenicity and mutagenicity of aromatic amines.	2.9	4	0	2-acetamidofluorenes	antimitotic; carcinogenic agent; epitope; mutagen
penicillin g Penicillin G: A penicillin derivative commonly used in the form of its sodium or potassium salts in the treatment of a variety of infections. It is effective against most gram-positive bacteria and against gram-negative cocci. It has also been used as an experimental convulsant because of its actions on GAMMA-AMINOBUTYRIC ACID mediated synaptic transmission.. benzylpenicillin : A penicillin in which the substituent at position 6 of the penam ring is a phenylacetamido group.	1.96	1	0	penicillin allergen; penicillin	antibacterial drug; drug allergen; epitope
triiodothyronine Triiodothyronine: A T3 thyroid hormone normally synthesized and secreted by the thyroid gland in much smaller quantities than thyroxine (T4). Most T3 is derived from peripheral monodeiodination of T4 at the 5' position of the outer ring of the iodothyronine nucleus. The hormone finally delivered and used by the tissues is mainly T3.. 3,3',5-triiodo-L-thyronine : An iodothyronine compound having iodo substituents at the 3-, 3'- and 5-positions. Although some is produced in the thyroid, most of the 3,3',5-triiodo-L-thyronine in the body is generated by mono-deiodination of L-thyroxine in the peripheral tissues. Its metabolic activity is about 3 to 5 times that of L-thyroxine. The sodium salt is used in the treatment of hypothyroidism.	2.66	3	0	2-halophenol; amino acid zwitterion; iodophenol; iodothyronine	human metabolite; mouse metabolite; thyroid hormone
isoflurophate Isoflurophate: A di-isopropyl-fluorophosphate which is an irreversible cholinesterase inhibitor used to investigate the NERVOUS SYSTEM.	2.64	3	0	dialkyl phosphate
carbon tetrachloride Carbon Tetrachloride: A solvent for oils, fats, lacquers, varnishes, rubber waxes, and resins, and a starting material in the manufacturing of organic compounds. Poisoning by inhalation, ingestion or skin absorption is possible and may be fatal. (Merck Index, 11th ed). tetrachloromethane : A chlorocarbon that is methane in which all the hydrogens have been replaced by chloro groups.	1.95	1	0	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
alanine Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.	11.76	47	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.	5.81	29	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.	9.38	21	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.	8.17	77	0	aspartate family amino acid; aspartic acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; mouse metabolite; neurotransmitter
glutamine Glutamine: A non-essential amino acid present abundantly throughout the body and is involved in many metabolic processes. It is synthesized from GLUTAMIC ACID and AMMONIA. It is the principal carrier of NITROGEN in the body and is an important energy source for many cells.. L-glutamine : An optically active form of glutamine having L-configuration.. glutamine : An alpha-amino acid that consists of butyric acid bearing an amino substituent at position 2 and a carbamoyl substituent at position 4.	9.86	42	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.	9.3	95	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.	3.07	5	0	pseudohalide anion	EC 1.9.3.1 (cytochrome c oxidase) inhibitor
physostigmine Physostigmine: A cholinesterase inhibitor that is rapidly absorbed through membranes. It can be applied topically to the conjunctiva. It also can cross the blood-brain barrier and is used when central nervous system effects are desired, as in the treatment of severe anticholinergic toxicity.	5.55	5	1	carbamate ester; indole alkaloid	antidote to curare poisoning; EC 3.1.1.8 (cholinesterase) inhibitor; miotic
sucrose Saccharum: A plant genus of the family POACEAE widely cultivated in the tropics for the sweet cane that is processed into sugar.	3.75	11	0	glycosyl glycoside	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; sweetening agent
puromycin aminonucleoside 3'-amino-3'-deoxy-N(6),N(6)-dimethyladenosine: structure in first source. 3'-amino-3'-deoxy-N(6),N(6)-dimethyladenosine : Puromycin derivative that lacks the methoxyphenylalanyl group on the amine of the sugar ring.	1.99	1	0	3'-deoxyribonucleoside; adenosines
adenosine diphosphate Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.	12.59	77	2	adenosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	fundamental metabolite; human metabolite
cephalothin Cephalothin: A cephalosporin antibiotic.. cefalotin : A semisynthetic, first-generation cephalosporin antibiotic with acetoxymethyl and (2-thienylacetyl)nitrilo moieties at positions 3 and 7, respectively, of the core structure. Administered parenterally during surgery and to treat a wide spectrum of blood infections.	2.08	1	0	azabicycloalkene; beta-lactam antibiotic allergen; carboxylic acid; cephalosporin; semisynthetic derivative; thiophenes	antibacterial drug; antimicrobial agent
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.	1.96	1	0	tetrachlorophenol	xenobiotic metabolite
uridine diphosphate Uridine Diphosphate: A uracil nucleotide containing a pyrophosphate group esterified to C5 of the sugar moiety.	2.8	3	0	pyrimidine ribonucleoside 5'-diphosphate; uridine 5'-phosphate	Escherichia coli metabolite; mouse metabolite
kanamycin a Kanamycin: Antibiotic complex produced by Streptomyces kanamyceticus from Japanese soil. Comprises 3 components: kanamycin A, the major component, and kanamycins B and C, the minor components.. kanamycin : Kanamycin is a naturally occurring antibiotic complex from Streptomyces kanamyceticus that consists of several components: kanamycin A, the major component (also usually designated as kanamycin), and kanamycins B, C, D and X the minor components.	3.57	9	0	kanamycins	bacterial metabolite
galactose galactopyranose : The pyranose form of galactose.	2.99	4	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.	1.98	1	0	monohydroxyquinoline; quinolone	bacterial xenobiotic metabolite
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.	3.75	11	0	ethylenediamine derivative; polyamino carboxylic acid; tetracarboxylic acid	anticoagulant; antidote; chelator; copper chelator; geroprotector
p-aminoazobenzene p-Aminoazobenzene: Used in the form of its salts as a dye and as an intermediate in manufacture of Acid Yellow, diazo dyes, and indulines.. 4-(phenylazo)aniline : Azobenzene substituted at one of the 4-positions by an amino group. It has a role as a dye and an allergen.	1.97	1	0
phenylethyl alcohol Phenylethyl Alcohol: An antimicrobial, antiseptic, and disinfectant that is used also as an aromatic essence and preservative in pharmaceutics and perfumery.. 2-phenylethanol : A primary alcohol that is ethanol substituted by a phenyl group at position 2.	2.15	1	0	benzenes; primary alcohol	Aspergillus metabolite; fragrance; plant growth retardant; plant metabolite; Saccharomyces cerevisiae metabolite
tyrosine Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.	5	7	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.	3.22	6	0	amine; thiol	geroprotector; human metabolite; mouse metabolite; radiation protective agent
phlorhizin [no description available]	2.36	2	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.	14.07	37	2	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.	1.95	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.	7.73	30	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]	1.96	1	0	anilines; primary arylamine
cytidine monophosphate Cytidine Monophosphate: Cytidine (dihydrogen phosphate). A cytosine nucleotide containing one phosphate group esterified to the sugar moiety in the 2', 3' or 5' position.. cytidine 5'-monophosphate : A pyrimidine ribonucleoside 5'-monophosphate having cytosine as the nucleobase.	2.05	1	0	cytidine 5'-phosphate; pyrimidine ribonucleoside 5'-monophosphate	Escherichia coli metabolite; human metabolite; mouse metabolite
cytidine diphosphate Cytidine Diphosphate: Cytidine 5'-(trihydrogen diphosphate). A cytosine nucleotide containing two phosphate groups esterified to the sugar moiety. Synonyms: CRPP; cytidine pyrophosphate.	2.36	2	0	cytidine 5'-phosphate; pyrimidine ribonucleoside 5'-diphosphate	Escherichia coli metabolite; mouse metabolite
uridine triphosphate Uridine Triphosphate: Uridine 5'-(tetrahydrogen triphosphate). A uracil nucleotide containing three phosphate groups esterified to the sugar moiety.	2.45	2	0	pyrimidine ribonucleoside 5'-triphosphate; uridine 5'-phosphate	Escherichia coli metabolite; mouse metabolite
lactose Lactose: A disaccharide of GLUCOSE and GALACTOSE in human and cow milk. It is used in pharmacy for tablets, in medicine as a nutrient, and in industry.. lactose : A glycosylglucose disaccharide, found most notably in milk, that consists of D-galactose and D-glucose fragments bonded through a beta-1->4 glycosidic linkage. The glucose fragment can be in either the alpha- or beta-pyranose form, whereas the galactose fragment can only have the beta-pyranose form.. beta-lactose : The beta-anomer of lactose.	2.95	4	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.	4.24	18	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.	4.79	10	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.	2.46	2	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.	3.46	8	0	antibiotic fungicide; cyclic ketone; dicarboximide; piperidine antibiotic; piperidones; secondary alcohol	anticoronaviral agent; bacterial metabolite; ferroptosis inhibitor; neuroprotective agent; protein synthesis inhibitor
egtazic acid Egtazic Acid: A chelating agent relatively more specific for calcium and less toxic than EDETIC ACID.. ethylene glycol bis(2-aminoethyl)tetraacetic acid : A diether that is ethylene glycol in which the hydrogens of the hydroxy groups have been replaced by 2-[bis(carboxymethyl)amino]ethyl group respectively.	3.36	7	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.	2.08	1	0	chloromethanes; one-carbon compound	carcinogenic agent; central nervous system drug; inhalation anaesthetic; non-polar solvent; refrigerant
cycloserine Cycloserine: Antibiotic substance produced by Streptomyces garyphalus.. D-cycloserine : A 4-amino-1,2-oxazolidin-3-one that has R configuration. It is an antibiotic produced by Streptomyces garyphalus or S. orchidaceus and is used as part of a multi-drug regimen for the treatment of tuberculosis when resistance to, or toxicity from, primary drugs has developed. An analogue of D-alanine, it interferes with bacterial cell wall synthesis in the cytoplasm by competitive inhibition of L-alanine racemase (which forms D-alanine from L-alanine) and D-alanine--D-alanine ligase (which incorporates D-alanine into the pentapeptide required for peptidoglycan formation and bacterial cell wall synthesis).	2.6	1	0	4-amino-1,2-oxazolidin-3-one; organonitrogen heterocyclic antibiotic; organooxygen heterocyclic antibiotic; zwitterion	antiinfective agent; antimetabolite; antitubercular agent; metabolite; NMDA receptor agonist
mannitol [no description available]	4.18	5	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.	4.12	16	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.	8.57	9	0	non-proteinogenic L-alpha-amino acid; ornithine	algal metabolite; hepatoprotective agent; mouse metabolite
asparagine Asparagine: A non-essential amino acid that is involved in the metabolic control of cell functions in nerve and brain tissue. It is biosynthesized from ASPARTIC ACID and AMMONIA by asparagine synthetase. (From Concise Encyclopedia Biochemistry and Molecular Biology, 3rd ed). asparagine : An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 2-amino-2-oxoethyl group.	2.68	3	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.	5.4	19	0	amino acid zwitterion; histidine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
n-pentanol n-pentanol: RN given refers to parent cpd. pentan-1-ol : A short-chain primary fatty alcohol that is pentane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It has been isolated from Melicope ptelefolia.	2.02	1	0	pentanol; short-chain primary fatty alcohol	human metabolite; plant metabolite
valine Valine: A branched-chain essential amino acid that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway.. valine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isopropyl group.. L-valine : The L-enantiomer of valine.	3.99	4	0	L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid; valine	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
threonine Threonine: An essential amino acid occurring naturally in the L-form, which is the active form. It is found in eggs, milk, gelatin, and other proteins.. threonine : An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 1-hydroxyethyl group.	10.46	20	0	amino acid zwitterion; aspartate family amino acid; L-alpha-amino acid; proteinogenic amino acid; threonine	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
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.	4.57	8	0	erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; tryptophan zwitterion; tryptophan	antidepressant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
isoleucine Isoleucine: An essential branched-chain aliphatic amino acid found in many proteins. It is an isomer of LEUCINE. It is important in hemoglobin synthesis and regulation of blood sugar and energy levels.. isoleucine : A 2-amino-3-methylpentanoic acid having either (2R,3R)- or (2S,3S)-configuration.. L-isoleucine : The L-enantiomer of isoleucine.	4.97	12	0	aspartate family amino acid; isoleucine; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
arginine Arginine: An essential amino acid that is physiologically active in the L-form.. arginine : An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group.	4.73	30	0	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
acetylene [no description available]	1.95	1	0	alkyne; gas molecular entity; terminal acetylenic compound
methyl iodide methyl iodide: RN given refers to unlabeled cpd with MF of CH3-I. iodomethane : A member of the class of iodomethanes that is methane in which one of the hydrogens is replaced by iodine.	1.97	1	0	iodomethanes; methyl halides	fumigant insecticide
propane Propane: A three carbon alkane with the formula H3CCH2CH3.	1.95	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.	2.06	1	0	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
carbon disulfide Carbon Disulfide: A colorless, flammable, poisonous liquid, CS2. It is used as a solvent, and is a counterirritant and has local anesthetic properties but is not used as such. It is highly toxic with pronounced CNS, hematologic, and dermatologic effects.	1.98	1	0	one-carbon compound; organosulfur compound
tert-butylhydroperoxide tert-Butylhydroperoxide: A direct-acting oxidative stress-inducing agent used to examine the effects of oxidant stress on Ca(2+)-dependent signal transduction in vascular endothelial cells. It is also used as a catalyst in polymerization reactions and to introduce peroxy groups into organic molecules.. tert-butyl hydroperoxide : An alkyl hydroperoxide in which the alkyl group is tert-butyl. It is widely used in a variety of oxidation processes.	2.02	1	0	alkyl hydroperoxide	antibacterial agent; oxidising agent
trichloroacetic acid Trichloroacetic Acid: A strong acid used as a protein precipitant in clinical chemistry and also as a caustic for removing warts.. trichloroacetic acid : A monocarboxylic acid that is acetic acid in which all three methyl hydrogens are substituted by chlorine.	1.95	1	0	monocarboxylic acid; organochlorine compound	carcinogenic agent; metabolite; mouse metabolite
3-mercaptopropionic acid 3-Mercaptopropionic Acid: An inhibitor of glutamate decarboxylase. It decreases the GAMMA-AMINOBUTYRIC ACID concentration in the brain, thereby causing convulsions.. 3-mercaptopropanoic acid : A mercaptopropanoic acid that is propanoic acid carrying a sulfanyl group at position 3.	2.05	1	0	mercaptopropanoic acid	algal metabolite
isoprene isoprene: used in manufacture of ''synthetic'' rubber, butyl rubber; copolymer in production of elastomers; structure. isoprene : A hemiterpene with the formula CH2=C(CH3)CH=CH2; the monomer of natural rubber and a common structure motif to the isoprenoids, a large class of other naturally occurring compounds.	4.87	6	0	alkadiene; hemiterpene; volatile organic compound	plant metabolite
isobutyl alcohol isobutyl alcohol: RN given refers to parent cpd	2.02	1	0	alkyl alcohol; primary alcohol	Saccharomyces cerevisiae metabolite
dichloroacetic acid [no description available]	8.5	24	2	monocarboxylic acid; organochlorine compound	astringent; marine metabolite
pantothenic acid Pantothenic Acid: A butyryl-beta-alanine that can also be viewed as pantoic acid complexed with BETA ALANINE. It is incorporated into COENZYME A and protects cells against peroxidative damage by increasing the level of GLUTATHIONE.. pantothenic acid : A member of the class of pantothenic acids that is an amide formed from pantoic acid and beta-alanine.. vitamin B5 : Any member of a group of vitamers that belong to the chemical structural class called pantothenic acids that exhibit biological activity against vitamin B5 deficiency. Deficiency of vitamin B5 is rare due to its widespread distribution in whole grain cereals, legumes and meat. Symptoms associated with vitamin B5 deficiency are difficult to asses since they are subtle and resemble those of other B vitamin deficiencies. The vitamers include (R)-pantothenic acid and its ionized and salt forms.. (R)-pantothenate : A pantothenate that is the conjugate base of (R)-pantothenic acid, obtained by deprotonation of the carboxy group.. (R)-pantothenic acid : A pantothenic acid having R-configuration.	6.05	22	0	pantothenic acid; vitamin B5	antidote to curare poisoning; geroprotector; human blood serum metabolite
cumene hydroperoxide cumene hydroperoxide: RN given refers to parent cpd. cumene hydroperoxide : A peroxol that is cumene in which the alpha-hydrogen is replaced by a hydroperoxy group.	2.02	1	0	peroxol	environmental contaminant; Mycoplasma genitalium metabolite; oxidising agent
taurocholic acid Taurocholic Acid: The product of conjugation of cholic acid with taurine. Its sodium salt is the chief ingredient of the bile of carnivorous animals. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and cholerectic.. taurocholate : An organosulfonate oxoanion that is the conjugate base of taurocholic acid.. taurocholic acid : A bile acid taurine conjugate of cholic acid that usually occurs as the sodium salt of bile in mammals.	2.15	1	0	amino sulfonic acid; bile acid taurine conjugate	human metabolite
rotenone Derris: A plant genus of the family FABACEAE. The root is a source of rotenoids (ROTENONE) and flavonoids. Some species of Pongamia have been reclassified to this genus and some to MILLETTIA. Some species of Deguelia have been reclassified to this genus.. rotenoid : Members of the class of tetrahydrochromenochromene that consists of a cis-fused tetrahydrochromeno[3,4-b]chromene skeleton and its substituted derivatives. The term was originally restricted to natural products, but is now also used to describe semi-synthetic and fully synthetic compounds.	3.5	8	0	organic heteropentacyclic compound; rotenones	antineoplastic agent; metabolite; mitochondrial NADH:ubiquinone reductase inhibitor; phytogenic insecticide; piscicide; toxin
1-nitronaphthalene 1-nitronaphthalene: RN given refers to cpd with locant for nitro moiety in 1 position. 1-nitronaphthalene : A mononitronaphthalene substituted by a nitro group at position 1.. mononitronaphthalene : A nitronaphthalene carrying a single nitro group at unspecified position.. nitronaphthalene : A nitroarene that is naphthalene substituted by at least one nitro group.	1.96	1	0	mononitronaphthalene	environmental contaminant; mouse metabolite
carbazole carbazole: structure in first source	2.03	1	0	carbazole
penicillanic acid Penicillanic Acid: A building block of penicillin, devoid of significant antibacterial activity. (From Merck Index, 11th ed). penicillanic acid : A penam that consists of 3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane bearing a carboxy group at position 2 and having (2S,5R)-configuration.	2.37	2	0	penicillanic acids
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
2-naphthylamine 2-Naphthylamine: A naphthalene derivative with carcinogenic action.. 2-naphthylamine : A naphthylamine carrying the amino group at position 2.	1.97	1	0	naphthylamine	carcinogenic agent
diphenyl diphenyl: RN given refers to unlabeled cpd; structure	2.03	1	0	aromatic fungicide; benzenes; biphenyls	antifungal agrochemical; antimicrobial food preservative
4-biphenylamine 4-biphenylamine: used in detection of sulfates, & as a carcinogen in cancer research; RN given refers to parent cpd; structure. biphenyl-4-amine : An aminobiphenyl that is biphenyl substituted by an amino group at position 4.	2.38	2	0	aminobiphenyl	carcinogenic agent
benzidine benzidine: RN given refers to parent cpd. benzidine : A member of the class of biphenyls that is 1,1'-biphenyl in which the hydrogen at the para-position of each phenyl group has been replaced by an amino group.	2.66	3	0	biphenyls; substituted aniline	carcinogenic agent
quinaldic acid [no description available]	2.01	1	0	quinolinemonocarboxylic acid	human metabolite; Saccharomyces cerevisiae 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)	1.97	1	0	benzoate ester; paraben; phenols	antifungal agent; antimicrobial agent
4-butyrolactone 4-Butyrolactone: One of the FURANS with a carbonyl thereby forming a cyclic lactone. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent.. tetrahydrofuranone : Any oxolane having an oxo- substituent at any position on the tetrahydrofuran ring.. gamma-butyrolactone : A butan-4-olide that is tetrahydrofuran substituted by an oxo group at position 2.	2.72	3	0	butan-4-olide	metabolite; neurotoxin
soman Soman: An organophosphorus compound that inhibits cholinesterase. It causes seizures and has been used as a chemical warfare agent.	2.04	1	0	phosphonic ester
trehalose alpha,alpha-trehalose : A trehalose in which both glucose residues have alpha-configuration at the anomeric carbon.	2.41	2	0	trehalose	Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
sym-trinitrobenzene Trinitrobenzenes: Benzene derivatives which are substituted with three nitro groups in any position.. 1,3,5-trinitrobenzene : A trinitrobenzene in which each of the nitro groups is meta- to the other two.	1.97	1	0	trinitrobenzene	explosive
4-bromophenacyl bromide 4-bromophenacyl bromide: phospholipidase A(2) inhibitor; structure	1.96	1	0
4-toluic acid 4-toluic acid: RN given refers to parent cpd; structure. p-toluic acid : A methylbenzoic acid in which the methyl substituent is located at position 4.	2.1	1	0	methylbenzoic acid
4-nitroaniline [no description available]	2.38	2	0	nitroaniline	bacterial xenobiotic metabolite
ethylbenzene [no description available]	3.1	1	0	alkylbenzene
styrene Styrene: A colorless, toxic liquid with a strong aromatic odor. It is used to make rubbers, polymers and copolymers, and polystyrene plastics.. styrene : A vinylarene that is benzene carrying a vinyl group. It has been isolated from the benzoin resin produced by Styrax species.	3.81	3	0	styrenes; vinylarene; volatile organic compound	mouse metabolite; mutagen; plant metabolite
phenylhydrazine [no description available]	1.94	1	0	phenylhydrazines	xenobiotic
quinuclidines Quinuclidines: A class of organic compounds which contain two rings that share a pair of bridgehead carbon atoms and contains an amine group.	1.95	1	0	quinuclidines; saturated organic heterobicyclic parent
caprolactam Caprolactam: Cyclic amide of caproic acid used in manufacture of synthetic fibers of the polyamide type. Can cause local irritation.. epsilon-caprolactam : A member of the class of caprolactams that is azepane substituted by an oxo group at position 2.	2.13	1	0	caprolactams	human blood serum metabolite
4-toluidine 4-toluidine: RN given refers to parent cpd. p-toluidine : An aminotoluene in which the amino substituent is para to the methyl group.	1.96	1	0	aminotoluene
4-vinyl-1-cyclohexene dioxide 4-vinyl-1-cyclohexene dioxide: activates caspase cascades; structure. 4-vinylcyclohexene dioxide : The diepoxide of 4-vinylcyclohexene.	2.25	1	0	epoxide	carcinogenic agent
sarin Sarin: An organophosphorus ester compound that produces potent and irreversible inhibition of cholinesterase. It is toxic to the nervous system and is a chemical warfare agent.. isopropyl methylphosphonofluoridate : A phosphinic ester that is the isopropyl ester of methylphosphonofluoridic acid.. sarin : A racemate composed of equal amounts of (R)- and (S)-sarin. A potent and irreversible inhibitor of acetylcholinesterase that is toxic to the nervous system and is employed as a chemical warfare agent.	1.95	1	0	fluorine molecular entity; phosphinic ester
diisopropyl ether [no description available]	2.01	1	0
acetic anhydride acetic anhydride: RN given refers to unlabeled cpd; structure. acetic anhydride : An acyclic carboxylic anhydride derived from acetic acid.	2.03	1	0	acyclic carboxylic anhydride	metabolite; reagent
maleic anhydride Maleic Anhydrides: Used in copolymerization reactions, in the Diels-Alder(diene)synthesis, in the preparation of resins, pharmaceuticals and agricultural chemicals. It is a powerful irritant and causes burns.. maleic anhydride : A cyclic dicarboxylic anhydride that is the cyclic anhydride of maleic acid.	1.97	1	0	cyclic dicarboxylic anhydride; furans	allergen
n-butyl n-butyrate n-butyl n-butyrate: structure. butyl butanoate : A butanoate ester of butan-1-ol.	2.31	1	0	butyrate ester	metabolite
pentane Pentanes: Five-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives.. pentane : A straight chain alkane consisting of 5 carbon atoms.	4.07	4	0	alkane; volatile organic compound	non-polar solvent; refrigerant
vinyl ether vinyl ether: major descriptor (65-85); on-line search VINYL COMPOUNDS (66-85); Index Medicus search VINYL ETHER (65-85)	2.13	1	0	ether
thiophenes Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.	2.91	4	0	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
thiodipropionic acid thiodipropionic acid: structure	2.05	1	0	dicarboxylic acid
undecanoic acid undecanoic acid : A straight-chain, eleven-carbon saturated medium-chain fatty acid found in body fluids; the most fungitoxic of the C7:0 - C18:0 fatty acid series.. undecanoate : A medium-chain fatty acid anion that is the conjugate base of undecanoic acid; used in tandem with testosterone cation in the treatment of male hypogonadism. Major species at pH 7.3.	2.07	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	antifungal agent; human metabolite
behenic acid behenic acid: RN given refers to parent cpd; structure. docosanoic acid : A straight-chain, C22, long-chain saturated fatty acid.	1.98	1	0	long-chain fatty acid; straight-chain saturated fatty acid	plant metabolite
propylene propylene: structure	3.35	1	0	alkene; gas molecular entity	refrigerant; xenobiotic
tetrafluoroethylene tetrafluoroethylene: RN given refers to parent cpd; structure	6.97	1	0	fluorocarbon
diethylhexyl phthalate Diethylhexyl Phthalate: An ester of phthalic acid. It appears as a light-colored, odorless liquid and is used as a plasticizer for many resins and elastomers.. bis(2-ethylhexyl) phthalate : A phthalate ester that is the bis(2-ethylhexyl) ester of benzene-1,2-dicarboxylic acid.	2.65	3	0	diester; phthalate ester	androstane receptor agonist; apoptosis inhibitor; plasticiser
trinitrotoluene Trinitrotoluene: A 2,4,6-trinitrotoluene, which is an explosive chemical that can cause skin irritation and other toxic consequences.. 2,4,6-trinitrotoluene : A trinitrotoluene having the nitro groups at positions 2, 4 and 6.	1.99	1	0	trinitrotoluene	explosive
framycetin Framycetin: A component of NEOMYCIN that is produced by Streptomyces fradiae. On hydrolysis it yields neamine and neobiosamine B. (From Merck Index, 11th ed). framycetin : A tetracyclic antibacterial agent derived from neomycin, being a glycoside ester of neamine and neobiosamine B.	2.88	4	0	aminoglycoside	allergen; antibacterial drug; Escherichia coli metabolite
dianisidine Dianisidine: Highly toxic compound which can cause skin irritation and sensitization. It is used in manufacture of azo dyes.	1.96	1	0	biphenyls
cyclopentanone [no description available]	2.11	1	0	cyclopentanones	Maillard reaction product
uridine diphosphate glucose Uridine Diphosphate Glucose: A key intermediate in carbohydrate metabolism. Serves as a precursor of glycogen, can be metabolized into UDPgalactose and UDPglucuronic acid which can then be incorporated into polysaccharides as galactose and glucuronic acid. Also serves as a precursor of sucrose lipopolysaccharides, and glycosphingolipids.. UDP-alpha-D-glucose : The alpha-anomer of UDP-alpha-D-glucose. It is used in nucleotide sugars metabolism.	2.38	2	0	UDP-D-glucose	fundamental metabolite
oxythiamine Oxythiamine: Thiamine antagonist, antimetabolite.. oxythiamine(1+) : A 1,3-thiazolium cation that is 5-(2-hydroxyethyl)-4-methyl-1,3-thiazole alkylated at the N3 position by a (2-methyl-4-oxo-1,4-dihydropyrimidin-5-yl)methyl group.	3.06	1	0	1,3-thiazolium cation	antimetabolite; vitamin B1 antagonist
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.	4.03	4	0	alpha,beta-unsaturated monocarboxylic acid; cyclohexenecarboxylic acid; hydroxy monocarboxylic acid	Escherichia coli metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
citronellol citronellol: alcohol form of citronellal; found in rose oil; RN given refers to parent cpd without isomeric designation; structure. citronellol : A monoterpenoid that is oct-6-ene substituted by a hydroxy group at position 1 and methyl groups at positions 3 and 7.. insect repellent : An insecticide that acts as a repellent to insects.	7	1	0	monoterpenoid	plant metabolite
ethyl acetate ethyl acetate : The acetate ester formed between acetic acid and ethanol.	4.46	6	0	acetate ester; ethyl ester; volatile organic compound	EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor; metabolite; polar aprotic solvent; Saccharomyces cerevisiae metabolite
hexanoic acid hexanoic acid : A C6, straight-chain saturated fatty acid.	2.71	3	0	medium-chain fatty acid; straight-chain saturated fatty acid	human metabolite; plant metabolite
sodium cyanide Sodium Cyanide: A highly poisonous compound that is an inhibitor of many metabolic processes and is used as a test reagent for the function of chemoreceptors. It is also used in many industrial processes.. sodium cyanide : A cyanide salt containing equal numbers of sodium cations and cyanide anions.	2.36	2	0	cyanide salt; one-carbon compound; sodium salt	EC 1.15.1.1 (superoxide dismutase) inhibitor
pregnenolone [no description available]	1.96	1	0	20-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; C21-steroid	human metabolite; mouse metabolite
ditiocarb Ditiocarb: A chelating agent that has been used to mobilize toxic metals from the tissues of humans and experimental animals. It is the main metabolite of DISULFIRAM.. diethyldithiocarbamic acid : A member of the class of dithiocarbamic acids that is diethylcarbamic acid in which both of the oxygens are replaced by sulfur.	1.97	1	0	dithiocarbamic acids	chelator; copper chelator
citronellyl acetate citronellyl acetate: RN given refers to cpd without isomeric designation. citronellol acetate : A monoterpenoid that is the acetate ester of citronellol. It has been isolated from Citrus hystrix.	7	1	0	acetate ester; monoterpenoid	plant metabolite
potassium cyanide [no description available]	2.39	2	0	cyanide salt; one-carbon compound; potassium salt	EC 1.15.1.1 (superoxide dismutase) inhibitor; EC 1.9.3.1 (cytochrome c oxidase) inhibitor; neurotoxin
catechin Catechin: An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.. catechin : Members of the class of hydroxyflavan that have a flavan-3-ol skeleton and its substituted derivatives.. rac-catechin : A racemate comprising equimolar amounts of (+)- and (-)-catechin. (+)-catechin : The (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite.	4.43	4	0	catechin	antioxidant; plant metabolite
thiamine pyrophosphate Thiamine Pyrophosphate: The coenzyme form of Vitamin B1 present in many animal tissues. It is a required intermediate in the PYRUVATE DEHYDROGENASE COMPLEX and the KETOGLUTARATE DEHYDROGENASE COMPLEX.. thiamine(1+) diphosphate chloride : An organic chloride salt of thiamine(1+) diphosphate.	10.78	17	0	organic chloride salt; vitamin B1
perylene Perylene: A 20-carbon dibenz(de,kl)anthracene that can be viewed as a naphthalene fused to a phenalene or as dinaphthalene. It is used as fluorescent lipid probe in the cytochemistry of membranes and is a polycyclic hydrocarbon pollutant in soil and water. Derivatives may be carcinogenic.. perylene : An ortho- and peri-fused polycyclic arene comprising of five benzene rings that is anthracene in which the d,e and k,l sides are fused to benzene rings.	2.41	1	0	ortho- and peri-fused polycyclic arene; perylenes
fluoranthene fluoranthene: structure. fluoranthene : An ortho- and peri-fused polycyclic arene consisting of a naphthalene and benzene unit connected by a five-membered ring.	2.03	1	0	ortho- and peri-fused polycyclic arene
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.	2.06	1	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinazolines
indazoles Indazoles: A group of heterocyclic aromatic organic compounds consisting of the fusion of BENZENE and PYRAZOLES.	2.41	2	0	indazole
cyclopentane Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.	2.47	2	0	cycloalkane; cyclopentanes; volatile organic compound	non-polar solvent
isoxazoles Isoxazoles: Azoles with an OXYGEN and a NITROGEN next to each other at the 1,2 positions, in contrast to OXAZOLES that have nitrogens at the 1,3 positions.. isoxazole : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing three carbon atoms and an oxygen and nitrogen atom adjacent to each other. It is the parent of the class of isoxazoles.. isoxazoles : Oxazoles in which the N and O atoms are adjacent.	2.15	1	0	isoxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
thiazoles [no description available]	2.75	3	0	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
pyrazines Pyrazines: A heterocyclic aromatic organic compound with the chemical formula C4H4N2.. pyrazine : A diazine that is benzene in which the carbon atoms at positions 1 and 4 have been replaced by nitrogen atoms.	2.21	1	0	diazine; pyrazines	Daphnia magna metabolite
nitroblue tetrazolium Nitroblue Tetrazolium: Colorless to yellow dye that is reducible to blue or black formazan crystals by certain cells; formerly used to distinguish between nonbacterial and bacterial diseases, the latter causing neutrophils to reduce the dye; used to confirm diagnosis of chronic granulomatous disease.	2.01	1	0	organic cation
allylisopropylacetamide Allylisopropylacetamide: An allylic compound that acts as a suicide inactivator of CYTOCHROME P450 by covalently binding to its heme moiety or surrounding protein.	1.95	1	0
hydrazine diamine : Any polyamine that contains two amino groups.	4.02	4	0	azane; hydrazines	EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
paraoxon [no description available]	2.66	3	0	aryl dialkyl phosphate; organophosphate insecticide	EC 3.1.1.7 (acetylcholinesterase) inhibitor; mouse metabolite
hemicholinium 3 Hemicholinium 3: A potent inhibitor of the high affinity uptake system for CHOLINE. It has less effect on the low affinity uptake system. Since choline is one of the components of ACETYLCHOLINE, treatment with hemicholinium can deplete acetylcholine from cholinergic terminals. Hemicholinium 3 is commonly used as a research tool in animal and in vitro experiments.	2.91	4	0
diazomethane Diazomethane: A diazonium compound with the formula CH2N2.. diazomethane : The simplest diazo compound, in which a diazo group is attached to a methylene group.	1.96	1	0	diazo compound	alkylating agent; antineoplastic agent; carcinogenic agent; poison
aminoimidazole carboxamide Aminoimidazole Carboxamide: An imidazole derivative which is a metabolite of the antineoplastic agents BIC and DIC. By itself, or as the ribonucleotide, it is used as a condensation agent in the preparation of nucleosides and nucleotides. Compounded with orotic acid, it is used to treat liver diseases.. 5-aminoimidazole-4-carboxamide : An aminoimidazole in which the amino group is at C-5 with a carboxamido group at C-4.	2.73	3	0	aminoimidazole; monocarboxylic acid amide	mouse metabolite
citrulline citrulline : The parent compound of the citrulline class consisting of ornithine having a carbamoyl group at the N(5)-position.	2.65	3	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.	1.97	1	0	nitrile; one-carbon compound	EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor
fluorobenzenes Fluorobenzenes: Derivatives of BENZENE that contain FLUORINE.. monofluorobenzene : The simplest member of the class of monofluorobenzenes that is benzene carrying a single fluoro substituent.. fluorobenzenes : Any fluoroarene that is a benzene or a substituted benzene carrying at least one fluoro group.	1.98	1	0	monofluorobenzenes	NMR chemical shift reference compound
mesoxalic acid mesoxalic acid: structure	1.96	1	0	oxo dicarboxylic acid
chenodeoxycholic acid Chenodeoxycholic Acid: A bile acid, usually conjugated with either glycine or taurine. It acts as a detergent to solubilize fats for intestinal absorption and is reabsorbed by the small intestine. It is used as cholagogue, a choleretic laxative, and to prevent or dissolve gallstones.. chenodeoxycholic acid : A dihydroxy-5beta-cholanic acid that is (5beta)-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 7 respectively.. chenodeoxycholate : Conjugate base of chenodeoxycholic acid; major species at pH 7.3.	2.4	2	0	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
fusarium Fusarium: A mitosporic Hypocreales fungal genus, various species of which are important parasitic pathogens of plants and a variety of vertebrates. Teleomorphs include GIBBERELLA.	3.43	6	0
plumbagin plumbagin: a superoxide anion generator. plumbagin : A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 2 and 5 are substituted by methyl and hydroxy groups, respectively.	2.41	1	0	hydroxy-1,4-naphthoquinone; phenols	anticoagulant; antineoplastic agent; immunological adjuvant; metabolite
phosphoadenosine phosphosulfate Phosphoadenosine Phosphosulfate: 3'-Phosphoadenosine-5'-phosphosulfate. Key intermediate in the formation by living cells of sulfate esters of phenols, alcohols, steroids, sulfated polysaccharides, and simple esters, such as choline sulfate. It is formed from sulfate ion and ATP in a two-step process. This compound also is an important step in the process of sulfur fixation in plants and microorganisms.. 3'-phospho-5'-adenylyl sulfate : An adenosine bisphosphate having monophosphate groups at the 3'- and 5'-positions and a sulfo group attached to the phosphate at position 5'.	2.91	4	0	acyl sulfate; adenosine bisphosphate; purine ribonucleoside bisphosphate	Escherichia coli metabolite; mouse metabolite
cytisine [no description available]	2.13	1	0	alkaloid; bridged compound; lactam; organic heterotricyclic compound; secondary amino compound	nicotinic acetylcholine receptor agonist; phytotoxin; plant metabolite
adenosine phosphosulfate Adenosine Phosphosulfate: 5'-Adenylic acid, monoanhydride with sulfuric acid. The initial compound formed by the action of ATP sulfurylase on sulfate ions after sulfate uptake. Synonyms: adenosine sulfatophosphate; APS.. 5'-adenylyl sulfate : An adenosine 5'-phosphate having a sulfo group attached to one the phosphate OH groups.	1.97	1	0	acyl monophosphate; acyl sulfate; adenosine 5'-phosphate	Escherichia coli metabolite; mouse metabolite
kainic acid Kainic Acid: (2S-(2 alpha,3 beta,4 beta))-2-Carboxy-4-(1-methylethenyl)-3-pyrrolidineacetic acid. Ascaricide obtained from the red alga Digenea simplex. It is a potent excitatory amino acid agonist at some types of excitatory amino acid receptors and has been used to discriminate among receptor types. Like many excitatory amino acid agonists it can cause neurotoxicity and has been used experimentally for that purpose.	2.01	1	0	dicarboxylic acid; L-proline derivative; non-proteinogenic L-alpha-amino acid; pyrrolidinecarboxylic acid	antinematodal drug; excitatory amino acid agonist
4-hydroxybutyric acid 4-hydroxybutyric acid: was an entry term to Sodium Oxybate (74-98). 4-hydroxybutyric acid : A 4-hydroxy monocarboxylic acid that is butyric acid in which one of the hydrogens at position 4 is replaced by a hydroxy group.	4.77	5	0	4-hydroxy monocarboxylic acid; hydroxybutyric acid	general anaesthetic; GHB receptor agonist; neurotoxin; sedative
isovaleric acid isovaleric acid: structure. isovaleric acid : A C5, branched-chain saturated fatty acid.	1.96	1	0	branched-chain saturated fatty acid; methylbutyric acid; short-chain fatty acid	mammalian metabolite; plant metabolite
1,3-propanediol propane-1,3-diol : The simplest member of the class of propane-1,3-diols, consisting of propane in which one hydrogen from each methyl group is substituted by a hydroxy group. A colourless, viscous, water-miscible liquid with a high (210degreeC) boiling point, it is used in the synthesis of certain polymers and as a solvent and antifreeze.	2.15	1	0	propane-1,3-diols	metabolite; protic solvent
suberic acid suberic acid: used in plastics industry; inhibits activity of some enzymes; RN given refers to parent cpd; structure. suberic acid : An alpha,omega-dicarboxylic acid that is the 1,6-dicarboxy derivative of hexane.	1.96	1	0	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	human metabolite
margaric acid margaric acid: RN given refers to unlabeled parent cpd. heptadecanoic acid : A C17 saturated fatty acid and trace component of fats in ruminants.	1.96	1	0	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; mammalian 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.	1.99	1	0
thioacetic acid ethanethioic S-acid : A thioacetic acid that is acetic acid in which the oxygen atom of the hydroxy group has been replaced by a sulfur atom.	2.58	2	0	thioacetic acid
oleanolic acid [no description available]	2.21	1	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	plant metabolite
gluconic acid gluconic acid: zinc gluconate has anti-inflammatory activity; RN given refers to (D)-isomer; all RRs refers to (D)-isomer unless otherwise noted. ketogluconic acid : A gluconic acid that contains a ketonic carbonyl group.. D-gluconic acid : A gluconic acid having D-configuration.	2.45	2	0	gluconic acid	chelator; Penicillium metabolite
copper gluconate Gluconates: Derivatives of gluconic acid (the structural formula HOCH2(CHOH)4COOH), including its salts and esters.	3.26	6	0	organic molecular entity
azomycin azomycin: RN given refers to parent cpd with specified locant; structure	2.15	1	0	C-nitro compound; imidazoles	antitubercular agent
uridine diphosphate n-acetylglucosamine Uridine Diphosphate N-Acetylglucosamine: Serves as the biological precursor of insect chitin, of muramic acid in bacterial cell walls, and of sialic acids in mammalian glycoproteins.	4.25	5	0
tropic acid tropic acid: acid moiety of ester alkaloids hyoscyamine & scopolamine; RN given refers to parent cpd with unspecified isomeric designation; structure. tropic acid : A 3-hydroxy monocarboxylic acid that is propionic acid in which one of the hydrogens at position 2 is substituted by a phenyl group, and one of the methyl hydrogens is substituted by a hydroxy group.	3.1	1	0	3-hydroxy monocarboxylic acid	human xenobiotic metabolite
pyrithiamine Pyrithiamine: A thiamine antagonist due to its inhibition of thiamine pyrophosphorylation. It is used to produce thiamine deficiency.. pyrithiamine : A pyridinium ion that is 3-(2-hydroxyethyl)-2-methylpyridine substituted at position 1 by a (4-amino-2-methylpyrimidin-5-yl)methyl group.	3.49	2	0
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.	7.05	1	0	amphetamines; secondary amine	central nervous system stimulant; environmental contaminant; neurotoxin; psychotropic drug; xenobiotic
senecioic acid senecioic acid: structure. 3-methylbut-2-enoic acid : A methyl-branched fatty acid that is but-2-enoic acid bearing a methyl substituent at position 3.	1.93	1	0	alpha,beta-unsaturated monocarboxylic acid; methyl-branched fatty acid; monounsaturated fatty acid; short-chain fatty acid	plant metabolite
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.	3.22	6	0	dialdehyde	biomarker
aceturic acid aceturic acid: structure. N-acetylglycine : An N-acylglycine where the acyl group is specified as acetyl.	1.96	1	0	N-acetyl-amino acid; N-acylglycine	human metabolite
myristic acid Myristic Acid: A saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. It is used to synthesize flavor and as an ingredient in soaps and cosmetics. (From Dorland, 28th ed). tetradecanoic acid : A straight-chain, fourteen-carbon, long-chain saturated fatty acid mostly found in milk fat.. tetradecanoate : A long-chain fatty acid anion that is the conjugate base of myristic acid; major species at pH 7.3.	2.72	3	0	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite
trinitrobenzenesulfonic acid Trinitrobenzenesulfonic Acid: A reagent that is used to neutralize peptide terminal amino groups.. 2,4,6-trinitrobenzenesulfonic acid : The arenesulfonic acid that is benzenesulfonic acid with three nitro substituents in the 2-, 4- and 6-positions.	3.05	5	0	arenesulfonic acid; C-nitro compound	epitope; explosive; reagent
gentian violet Gentian Violet: A dye that is a mixture of violet rosanilinis with antibacterial, antifungal, and anthelmintic properties.. crystal violet : An organic chloride salt that is the monochloride salt of crystal violet cation. It has been used in creams for the topical treatment of bacterial and fungal infections, being effective against some Gram-positive bacteria (notably Staphylococcus species) and some pathogenic fungi (including Candida species) but use declined following reports of animal carcinogenicity. It has also been used for dying wood, silk, and paper, as well as a histological stain.	1.95	1	0	organic chloride salt	anthelminthic drug; antibacterial agent; antifungal agent; antiseptic drug; histological dye
aminopenicillanic acid aminopenicillanic acid: RN given refers to parent cpd; structure. 6-aminopenicillanic acid : A penicillanic acid compound having a (6R)-amino substituent. The active nucleus common to all penicillins, it may be substituted at the 6-amino position to form the semisynthetic penicillins, resulting in a variety of antibacterial and pharmacologic characteristics.	2.37	2	0	amino acid zwitterion; penicillanic acids	allergen
glycerylphosphorylcholine Glycerylphosphorylcholine: A component of PHOSPHATIDYLCHOLINES or LECITHINS, in which the two hydroxy groups of GLYCEROL are esterified with fatty acids. (From Stedman, 26th ed)	2.65	3	0	glycerophosphocholine
6-methylsalicylic acid 6-methylsalicylic acid: structure. 6-methylsalicylic acid : A monohydroxybenzoic acid that is salicylic acid in which the hydrogen ortho to the carboxylic acid group is substituted by a methyl group.	2.04	1	0	monohydroxybenzoic acid	Penicillium metabolite; plant metabolite
levulinic acid levulinic acid: inhibits 5-aminolevulinic acid dehydratase; RN given refers to parent cpd; structure in Merck Index, 9th ed, #5316. 4-oxopentanoic acid : An oxopentanoic acid with the oxo group in the 4-position.	2.06	1	0	oxopentanoic acid; straight-chain saturated fatty acid	plant metabolite
alpha-naphthoflavone alpha-naphthoflavone: inhibits P4501A1 and P4501A2; stimulates some activities of P4503A4. alpha-naphthoflavone : An extended flavonoid resulting from the formal fusion of a benzene ring with the h side of flavone. A synthetic compound, it is an inhibitor of aromatase (EC 1.14.14.14).	2.03	1	0	extended flavonoid; naphtho-gamma-pyrone; organic heterotricyclic compound	aryl hydrocarbon receptor agonist; aryl hydrocarbon receptor antagonist; EC 1.14.14.14 (aromatase) inhibitor
n,n'-diacetylbenzidine N,N'-diacetylbenzidine: induces glomerular epithelial cell lesions; structure	1.96	1	0	biphenyls
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.	1.99	1	0	hydroxy monocarboxylic acid; phenols	human metabolite; mouse metabolite
2-pyrrolidone 2-pyrrolidone: RN given refers to parent cpd. pyrrolidin-2-one : The simplest member of the class of pyrrolidin-2-ones, consisting of pyrrolidine in which the hydrogens at position 2 are replaced by an oxo group. The lactam arising by the formal intramolecular condensation of the amino and carboxy groups of gamma-aminobutyric acid (GABA).	2.41	1	0	pyrrolidin-2-ones	metabolite; polar solvent
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	3.11	5	0	acetylcysteine; L-cysteine derivative; N-acetyl-L-amino acid	antidote to paracetamol poisoning; antiinfective agent; antioxidant; antiviral drug; ferroptosis inhibitor; geroprotector; human metabolite; mucolytic; radical scavenger; vulnerary
chorismic acid Chorismic Acid: A cyclohexadiene carboxylic acid derived from SHIKIMIC ACID and a precursor for the biosynthesis of UBIQUINONE and the AROMATIC AMINO ACIDS.. chorismic acid : The (3R,4R)-stereoisomer of 5-[(1-carboxyethenyl)oxy]-6-hydroxycyclohexa-1,3-diene-1-carboxylic acid.	2.15	1	0	5-[(1-carboxyethenyl)oxy]-6-hydroxycyclohexa-1,3-diene-1-carboxylic acid	Escherichia coli metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
3-ethylphenol [no description available]	2.25	1	0	phenols
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.	2.39	2	0	cyclic ketone; erythromycin
precocene ii precocene II: has antibacterial, antifungal, insecticidal, and antioxidant activities; from plants of genus Ageratum; an antiallotropin compound capable of inhibiting juvenile hormone biosynthesis	2.08	1	0	chromenes	precocenes
homoserine homoserine : An alpha-amino acid that is glycine substituted at the alpha-position by a 2-hydroxyethyl group.. L-homoserine : The L-enantiomer of homoserine.	3.1	5	0	amino acid zwitterion; homoserine	algal metabolite; Escherichia coli metabolite; human metabolite; Saccharomyces cerevisiae metabolite
methylnitrosourea Methylnitrosourea: A nitrosourea compound with alkylating, carcinogenic, and mutagenic properties.. N-methyl-N-nitrosourea : A member of the class of N-nitrosoureas that is urea in which one of the nitrogens is substituted by methyl and nitroso groups.	2.15	1	0	N-nitrosoureas	alkylating agent; carcinogenic agent; mutagen; teratogenic agent
dodecanedioic acid dodecanedioic acid: RN given refers to parent cpd. dodecanedioic acid : An alpha,omega-dicarboxylic acid that is dodecane in which the methyl groups have been oxidised to the corresponding carboxylic acids.	1.96	1	0	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	EC 1.1.1.1 (alcohol dehydrogenase) inhibitor; human metabolite
4-nitrophenyl acetate [no description available]	2.74	3	0	C-nitro compound; phenyl acetates
hydroxyethyl methacrylate hydroxyethyl methacrylate: many of cited refs are for gel which refers to polymeric form of above cpd: POLYHYDROXYETHYL METHACRYLATE. 2-hydroxyethyl methacrylate : An enoate ester that is the monomethacryloyl derivative of ethylene glycol.	1.97	1	0	enoate ester	allergen; polymerisation monomer
cyclopentenone 2-cyclopenten-1-one : An enone that is cyclopentanone having a C=C double bond at position 2.	2.11	1	0	alicyclic ketone; enone	Hsp70 inducer
2,6-dichloroindophenol 2,6-Dichloroindophenol: A dye used as a reagent in the determination of vitamin C.. 2,6-dichloroindophenol : A quinone imine that is indophenol substituted by chloro groups at positions 2 and 6.. N-3,5-dichloro-4-hydroxyphenyl-1,4-benzoquinone imine : 1,4-benzoquinone imine having a 3,5-dichloro-4-hydroxyphenyl substituent attached to the nitrogen atom.	1.95	1	0	dichlorobenzene; quinone imine
cytidine diphosphate choline Cytidine Diphosphate Choline: Donor of choline in biosynthesis of choline-containing phosphoglycerides.	1.95	1	0	nucleotide-(amino alcohol)s; phosphocholines	human metabolite; mouse metabolite; neuroprotective agent; psychotropic drug; Saccharomyces cerevisiae metabolite
tri-n-butylphosphine [no description available]	2.13	1	0
pentadecanoic acid pentadecanoic acid: in serum as a marker for intake of milk fat. pentadecanoic acid : A straight-chain saturated fatty acid containing fifteen-carbon atoms.	2.02	1	0	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; food component; human blood serum metabolite; plant metabolite
ethambutol Ethambutol: An antitubercular agent that inhibits the transfer of mycolic acids into the cell wall of the tubercle bacillus. It may also inhibit the synthesis of spermidine in mycobacteria. The action is usually bactericidal, and the drug can penetrate human cell membranes to exert its lethal effect. (From Smith and Reynard, Textbook of Pharmacology, 1992, p863). ethambutol : An ethylenediamine derivative that is ethane-1,2-diamine in which one hydrogen attached to each of the nitrogens is sutstituted by a 1-hydroxybutan-2-yl group (S,S-configuration). It is a bacteriostatic antimycobacterial drug, effective against Mycobacterium tuberculosis and some other mycobacteria. It is used (as the dihydrochloride salt) in combination with other antituberculous drugs in the treatment of pulmonary and extrapulmonary tuberculosis; resistant strains of M. tuberculosis are readily produced if ethambutol is used alone.	2.06	1	0	ethanolamines; ethylenediamine derivative	antitubercular agent; environmental contaminant; xenobiotic
phenylglyoxal [no description available]	2.88	4	0	phenylacetaldehydes
benzyl viologen Benzyl Viologen: 1,1'-Bis(phenylmethyl)4,4'-bipyridinium dichloride. Oxidation-reduction indicator.	2.08	1	0	bipyridines
tetramethylpyrazine tetramethylpyrazine: found in Ligusticum chuanxiong. tetramethylpyrazine : A member of the class of pyrazines that is pyrazine in which all four hydrogens have been replaced by methyl groups. An alkaloid extracted from Chuanxiong (Ligusticum wallichii).	2.21	1	0	alkaloid; pyrazines	antineoplastic agent; apoptosis inhibitor; bacterial metabolite; neuroprotective agent; platelet aggregation inhibitor; vasodilator agent
2-acetamidoethanethiol 2-acetamidoethanethiol: structure. N-acetylcysteamine : A member of the class of acetamides that is the N-acetyl-deriavtive of cysteamine.	1.96	1	0	acetamides	metabolite
arsenic pentoxide [no description available]	1.97	1	0
durapatite Durapatite: The mineral component of bones and teeth; it has been used therapeutically as a prosthetic aid and in the prevention and treatment of osteoporosis.. hydroxylapatite : A phosphate mineral with the formula Ca5(PO4)3(OH).	1.98	1	0
ferrous sulfide ferrous sulfide: RN given refers to cpd with MF of Fe-S; mackinawite & troilite both have MF Fe-S	1.99	1	0
arsenic trioxide Arsenic Trioxide: An inorganic compound with the chemical formula As2O3 that is used for the treatment of ACUTE PROMYELOCYTIC LEUKEMIA in patients who have relapsed from, or are resistant to, conventional drug therapy.	1.97	1	0
selenomethionine [no description available]	2.7	3	0	selenoamino acid; selenomethionines	plant metabolite
ethyldimethylaminopropyl carbodiimide Ethyldimethylaminopropyl Carbodiimide: Carbodiimide cross-linking reagent.	2	1	0
paraquat Paraquat: A poisonous dipyridilium compound used as contact herbicide. Contact with concentrated solutions causes irritation of the skin, cracking and shedding of the nails, and delayed healing of cuts and wounds.. paraquat : An organic cation that consists of 4,4'-bipyridine bearing two N-methyl substituents loctated at the 1- and 1'-positions.	1.99	1	0	organic cation	geroprotector; herbicide
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.	1.99	1	0	aromatic amine; guanidines; organochlorine compound; pyrazines	diuretic; sodium channel blocker
phenylphosphonothioic acid, 2-ethyl 2-(4-nitrophenyl) ester Phenylphosphonothioic Acid, 2-Ethyl 2-(4-Nitrophenyl) Ester: An organothiophosphorus cholinesterase inhibitor that is used as an insecticide and as a acaricide.	1.94	1	0	organic phosphonate; organothiophosphate insecticide; phosphonic ester	acaricide; agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor
azetidyl-2-carboxylic acid azetidyl-2-carboxylic acid: a proline analog (with 4-membered ring in place of 5); a toxic non-protein amino acid that is misincorporated into protein in place of proline; induces nonfunctional heat-shock proteins; inhibits acquired thermotolerance; RN given refers to (L)-isomer; found in beets and Liliaceae. (S)-azetidine-2-carboxylic acid : The (S)-enantiomer of azetidine-2-carboxylic acid.. azetidinecarboxylic acid : A member of the class of azetidines that is azetidine substituted by at least one carboxy group at unspecified position.	2.04	1	0	azetidine-2-carboxylic acid
methyl methanethiosulfonate S-methyl methanethiosulfonate : A sulfonic acid derivative obtained by condensaton of methanesulfonic acid with methanethiol.	2.37	2	0	sulfonic acid derivative; thiosulfonate ester	metabolite
uridine diphosphate galactose Uridine Diphosphate Galactose: A nucleoside diphosphate sugar which can be epimerized into UDPglucose for entry into the mainstream of carbohydrate metabolism. Serves as a source of galactose in the synthesis of lipopolysaccharides, cerebrosides, and lactose.. UDP-alpha-D-galactose : A UDP-D-galactose in which the anomeric centre of the galactose moiety has alpha-configuration.	1.98	1	0	UDP-D-galactose	mouse metabolite
trimethylolpropane trimethacrylate trimethylolpropane trimethacrylate: acrylate derivative found in ultraviolet curing inks; structure in 1st source	1.97	1	0	carbonyl compound
n-acetylbenzidine [no description available]	1.96	1	0
sabinene sabinene: RN given refers to cpd without isomeric designation. sabinene : A thujene that is a bicyclic monoterpene isolated from the essential oils of various plant species.	2.58	2	0	thujene	plant metabolite
mannose mannopyranose : The pyranose form of mannose.	2.66	3	0	D-aldohexose; D-mannose; mannopyranose	metabolite
dithiothreitol 1,4-dimercaptobutane-2,3-diol : A glycol that is butane-2,3-diol in which a hydrogen from each of the methyl groups is replaced by a thiol group.. 1,4-dithiothreitol : The threo-diastereomer of 1,4-dimercaptobutane-2,3-diol.	9.36	21	0	1,4-dimercaptobutane-2,3-diol; butanediols; dithiol; glycol; thiol	chelator; human metabolite; reducing agent
phenoxyacetic acid phenoxyacetic acid : A monocarboxylic acid that is the O-phenyl derivative of glycolic acid. A metabolite of 2-phenoxyethanol, it is used in the manufacture of pharmaceuticals, pesticides, fungicides and dyes.	2	1	0	aromatic ether; monocarboxylic acid	allergen; Aspergillus metabolite; human xenobiotic metabolite; plant growth retardant
ecdysone [no description available]	2.31	1	0	14alpha-hydroxy steroid; 22-hydroxy steroid; 25-hydroxy steroid; 2beta-hydroxy steroid; 3beta-sterol; 6-oxo steroid; ecdysteroid	prohormone
uridine diphosphate xylose Uridine Diphosphate Xylose: The decarboxylation product of UDPglucuronic acid, which is used for formation of the xylosides of seryl hydroxyl groups in mucoprotein synthesis. Also forms plant xylans.	1.98	1	0	UDP-sugar	fundamental metabolite
n-hydroxy-n-(2-fluorenyl)benzamide N-hydroxy-N-(2-fluorenyl)benzamide: structure given in first source	1.98	1	0
nafenopin Nafenopin: A peroxisome proliferator that is used experimentally to promote liver tumors. It has been used as an antihyperlipoproteinemic agent.. nafenopin : A racemate comprising equimolar amounts of (R)- and (S)-nafenopin. It is a peroxisome proliferator that is used experimentally to promote liver tumors. It has been used as an hypolipidemic agent.. 2-methyl-2-[4-(1,2,3,4-tetrahydronaphthalen-1-yl)phenoxy]propanoic acid : A monocarboxylic acid that is 2-hydroxy-2-methylpropanoic acid in which ther tertiary hydroxy group has been converted into the corresponding p-(1,2,3,4-tetrahydronaphthalen-1-yl)phenyl ether.	1.98	1	0	aromatic ether; monocarboxylic acid
streptomycin [no description available]	2.36	2	0	antibiotic antifungal drug; antibiotic fungicide; streptomycins	antibacterial drug; antifungal agrochemical; antimicrobial agent; antimicrobial drug; bacterial metabolite; protein synthesis inhibitor
carbonates Carbonates: Salts or ions of the theoretical carbonic acid, containing the radical CO2(3-). Carbonates are readily decomposed by acids. The carbonates of the alkali metals are water-soluble; all others are insoluble. (From Grant & Hackh's Chemical Dictionary, 5th ed). carbonates : Organooxygen compounds that are salts or esters of carbonic acid, H2CO3.	3.45	2	0	carbon oxoanion
4-acetylaminobiphenyl [no description available]	1.98	1	0	biphenyls
fructosamine Fructosamine: An amino sugar formed when glucose non-enzymatically reacts with the N-terminal amino group of proteins. The fructose moiety is derived from glucose by the classical Amadori rearrangement.	2.02	1	0
n-hydroxy-4-acetylaminobiphenyl N-hydroxy-4-acetylaminobiphenyl: structure. N-hydroxy-4-acetylaminobiphenyl : A hydroxamic acid that is biphenyl-4-amine bearing N-hydroxy and N-acetyl substituents.	1.98	1	0	hydroxamic acid
acetylthiocholine Acetylthiocholine: An agent used as a substrate in assays for cholinesterases, especially to discriminate among enzyme types.	1.97	1	0
1-nitropyrene [no description available]	1.96	1	0	nitroarene	carcinogenic agent
acetoxyacetylaminofluorene Acetoxyacetylaminofluorene: An alkylating agent that forms DNA ADDUCTS at the C-8 position in GUANINE, resulting in single strand breaks. It has demonstrated carcinogenic action.. N-acetoxy-2-acetamidofluorene : A 2-acetamidofluorene compound in which the parent 2-acetamidofluorene is substituted on nitrogen by an acetoxy group.	1.97	1	0	2-acetamidofluorenes	carcinogenic agent; mutagen
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.	2.06	1	0	amino dicarboxylic acid; D-alpha-amino acid; D-aspartic acid derivative; secondary amino compound	neurotransmitter agent
homocholine homocholine: record includes halides; iodide used as internal standard for paired-ion HPLC assay for choline; RN given refers to parent cpd	1.95	1	0
dimethylpropiothetin dimethylpropiothetin: has antineoplastic activity; RN given refers to hydroxide inner salt. S,S-dimethyl-beta-propiothetin : A sulfonium betaine obtained by deprotonation of the carboxy group of 3-dimethylsulfoniopropionic acid.	2.75	3	0	sulfonium betaine	marine metabolite; osmolyte
manganese Manganese: A trace element with atomic symbol Mn, atomic number 25, and atomic weight 54.94. It is concentrated in cell mitochondria, mostly in the pituitary gland, liver, pancreas, kidney, and bone, influences the synthesis of mucopolysaccharides, stimulates hepatic synthesis of cholesterol and fatty acids, and is a cofactor in many enzymes, including arginase and alkaline phosphatase in the liver. (From AMA Drug Evaluations Annual 1992, p2035). manganese(4+) : A manganese cation that is monoatomic and has a formal charge of +4.	4.03	15	0	elemental manganese; manganese group element atom	Escherichia coli metabolite; micronutrient
mercury Mercury: A silver metallic element that exists as a liquid at room temperature. It has the atomic symbol Hg (from hydrargyrum, liquid silver), atomic number 80, and atomic weight 200.59. Mercury is used in many industrial applications and its salts have been employed therapeutically as purgatives, antisyphilitics, disinfectants, and astringents. It can be absorbed through the skin and mucous membranes which leads to MERCURY POISONING. Because of its toxicity, the clinical use of mercury and mercurials is diminishing.. mercury(0) : Elemental mercury of oxidation state zero.	2.93	4	0	elemental mercury; zinc group element atom	neurotoxin
molybdenum Molybdenum: A metallic element with the atomic symbol Mo, atomic number 42, and atomic weight 95.95. It is an essential trace element, being a component of the enzymes xanthine oxidase, aldehyde oxidase, and nitrate reductase.	2.08	1	0	chromium group element atom	micronutrient
vanadium Vanadium: A metallic element with the atomic symbol V, atomic number 23, and atomic weight 50.94. It is used in the manufacture of vanadium steel. Prolonged exposure can lead to chronic intoxication caused by absorption usually via the lungs.	2.4	2	0	elemental vanadium; vanadium group element atom	micronutrient
magnesium sulfate Magnesium Sulfate: A small colorless crystal used as an anticonvulsant, a cathartic, and an electrolyte replenisher in the treatment of pre-eclampsia and eclampsia. It causes direct inhibition of action potentials in myometrial muscle cells. Excitation and contraction are uncoupled, which decreases the frequency and force of contractions. (From AMA Drug Evaluations Annual, 1992, p1083). magnesium sulfate : A magnesium salt having sulfate as the counterion.	1.95	1	0	magnesium salt; metal sulfate; organic magnesium salt	anaesthetic; analgesic; anti-arrhythmia drug; anticonvulsant; calcium channel blocker; cardiovascular drug; fertilizer; tocolytic agent
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.	2.39	2	0	mercury coordination entity	sensitiser
acetylglucosamine Acetylglucosamine: The N-acetyl derivative of glucosamine.. N-acetyl-beta-D-glucosamine : An N-acetyl-D-glucosamine having beta-configuration at the anomeric centre.	3.47	7	0	N-acetyl-D-glucosamine	epitope
galactosamine 2-amino-2-deoxy-D-galactopyranose : The pyranose form of D-galactosamine.. D-galactosamine : The D-stereoisomer of galactosamine.	2.4	2	0	D-galactosamine; primary amino compound	toxin
isopentenyladenosine Isopentenyladenosine: N(6)-[delta(3)-isopentenyl]adenosine. Isopentenyl derivative of adenosine which is a member of the cytokinin family of plant growth regulators.. N(6)-(Delta(2)-isopentenyl)adenosine : A nucleoside analogue in which adenosine has been modified by substitution at the 6-amino nitrogen by a Delta(2)-isopentenyl group.	3.05	1	0	N-ribosyl-N(6)-isopentenyladenine; nucleoside analogue	antineoplastic agent; plant growth regulator; plant metabolite
bromine Bromine: A halogen with the atomic symbol Br, atomic number 35, and atomic weight 79.904. It is a volatile reddish-brown liquid that gives off suffocating vapors, is corrosive to the skin, and may cause severe gastroenteritis if ingested.	2.35	2	0	diatomic bromine
sodium sulfate [no description available]	3.06	1	0	inorganic sodium salt
tricalcium phosphate tricalcium phosphate: a form of tricalcium phosphate used as bioceramic bone replacement material; see also records for alpha-tricalcium phosphate, beta-tricalcium phosphate, calcium phosphate; apatitic tricalcium phosphate Ca9(HPO4)(PO4)5(OH) is the calcium orthophosphate leading to beta tricalcium phosphate Ca3(PO4)2 (b-TCP). calcium phosphate : A calcium salt composed of calcium and phosphate/diphosphate ions; present in milk and used for the mineralisation of calcified tissues.	1.95	1	0	calcium phosphate
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	4.12	16	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.	3.59	9	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.	3.97	4	0	diatomic chlorine; gas molecular entity	bleaching agent
deuterium oxide Deuterium Oxide: The isotopic compound of hydrogen of mass 2 (deuterium) with oxygen. (From Grant & Hackh's Chemical Dictionary, 5th ed) It is used to study mechanisms and rates of chemical or nuclear reactions, as well as biological processes.	2.45	2	0	deuterated compound; water	NMR solvent
molybdate ion molybdate : A divalent inorganic anion obtained by removal of both protons from molybdic acid	2.08	1	0	divalent inorganic anion; molybdenum oxoanion	Escherichia coli metabolite
galactose aldohexose : A hexose with a (potential) aldehyde group at one end.	2.7	3	0
ammonium ferric sulfate ammonium ferrous sulfate: supplies nutritional iron. ferrous ammonium sulfate (anhydrous) : A compound of ammonium, iron and sulfate in which the ratio of ammonium to iron(2+) to sulfate ions is 2:1:2.	1.98	1	0	ammonium salt; iron molecular entity; metal sulfate	ferroptosis inducer
carbendazim carbendazim: carcinogen when combined with sodium nitrite; principle metabolite of thiophanate methyl & benomyl; structure. carbendazim : A member of the class of benzimidazoles that is 2-aminobenzimidazole in which the primary amino group is substituted by a methoxycarbonyl group. A fungicide, carbendazim controls Ascomycetes, Fungi Imperfecti, and Basidiomycetes on a wide variety of crops, including bananas, cereals, cotton, fruits, grapes, mushrooms, ornamentals, peanuts, sugarbeet, soybeans, tobacco, and vegetables.	2.25	1	0	benzimidazole fungicide; benzimidazoles; benzimidazolylcarbamate fungicide; carbamate ester	antifungal agrochemical; antinematodal drug; metabolite; microtubule-destabilising agent
ammonium chloride Ammonium Chloride: An acidifying agent that has expectorant and diuretic effects. Also used in etching and batteries and as a flux in electroplating.. ammonium chloride : An inorganic chloride having ammonium as the counterion.	2.65	3	0	ammonium salt; inorganic chloride	ferroptosis inhibitor
dimethyl alpha-ketoglutarate [no description available]	2.1	1	0	oxo carboxylic acid
tetrathionic acid Tetrathionic Acid: A sulfuric acid dimer, formed by disulfide linkage. This compound has been used to prolong coagulation time and as an antidote in cyanide poisoning.	1.95	1	0	sulfur oxoacid
3-hydroxyoctanoic acid 3-hydroxyoctanoic acid : An 8-carbon, beta-hydroxy fatty acid which may be a marker for primary defects of beta-hydroxy fatty acid metabolism. Repeating unit of poly(3-hydroxyoctanoic acid), a biopolymer used by numerous bacterial species as carbon and energy reserves.	2.05	1	0	3-hydroxy fatty acid; 3-hydroxy monocarboxylic acid; medium-chain fatty acid
2,3,5-trimethylpyrazine 2,3,5-trimethylpyrazine: key aroma compound in beef extract. trimethylpyrazine : A member of the class of pyrazines that is pyrazine in which three hydrogens at positions 2, 3 and 5 have been replaced by methyl groups.	2.21	1	0	pyrazines	animal metabolite; bacterial metabolite; flavouring agent; pheromone; plant metabolite
phytanic acid Phytanic Acid: A 20-carbon branched chain fatty acid. In phytanic acid storage disease (REFSUM DISEASE) this lipid may comprise as much as 30% of the total fatty acids of the plasma. This is due to a phytanic acid alpha-hydroxylase deficiency.. phytanic acid : A branched-chain saturated fatty acid consisting of hexadecanoic acid carrying methyl substituents at positions 3, 7, 11 and 15.	1.95	1	0	branched-chain saturated fatty acid; long-chain fatty acid; methyl-branched fatty acid
tetradecanoylphorbol acetate Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.	1.98	1	0	acetate ester; diester; phorbol ester; tertiary alpha-hydroxy ketone; tetradecanoate ester	antineoplastic agent; apoptosis inducer; carcinogenic agent; mitogen; plant metabolite; protein kinase C agonist; reactive oxygen species generator
nickel sulfide nickel sulfide: RN given refers to cpd with MF of Ni-S; see also nickel subsulfide: 12035-72-2	1.99	1	0
fluorides [no description available]	3.06	5	0	halide anion; monoatomic fluorine
homocitric acid [no description available]	2.73	3	0	tricarboxylic acid
cresyl violet cresyl violet: RN given refers to chloride. cresyl violet : A cationic heterotetracyclic fluorescent dye derived from benzo[a]phenoxazine.	1.96	1	0
4-amino-2,6-dinitrotoluene 4-amino-2,6-dinitrotoluene : An amino-nitrotoluene that is 2,6-dinitrotoluene substituted at position 4 by an amino group.	1.99	1	0	amino-nitrotoluene	explosive; fungal xenobiotic metabolite; marine metabolite
iodine [no description available]	1.95	1	0	halide anion; monoatomic iodine	human metabolite
daunorubicin Daunorubicin: A very toxic anthracycline aminoglycoside antineoplastic isolated from Streptomyces peucetius and others, used in treatment of LEUKEMIA and other NEOPLASMS.. anthracycline : Anthracyclines are polyketides that have a tetrahydronaphthacenedione ring structure attached by a glycosidic linkage to the amino sugar daunosamine.. daunorubicin : A natural product found in Actinomadura roseola.	2.46	2	0	aminoglycoside antibiotic; anthracycline; p-quinones; tetracenequinones	antineoplastic agent; bacterial metabolite
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.	14.83	370	2	benzenes; phenyl acetates
2,5-dimethylpyrazine [no description available]	2.21	1	0	pyrazines
ethyl hexanoate ethyl hexanoate : A fatty acid ethyl ester obtained by the formal condensation of hexanoic acid with ethanol.	2.13	1	0	fatty acid ethyl ester; hexanoate ester	metabolite
butyl acetate butyl acetate: structure. butyl acetate : The acetate ester of butanol.	2.76	2	0	acetate ester	metabolite
isoamyl acetate isoamyl acetate: structure in Merck, 9th ed, #4958. isoamyl acetate : The acetate ester of isoamylol.	2.02	1	0	acetate ester	metabolite; Saccharomyces cerevisiae metabolite
ursodeoxycholic acid Ursodeoxycholic Acid: An epimer of chenodeoxycholic acid. It is a mammalian bile acid found first in the bear and is apparently either a precursor or a product of chenodeoxycholate. Its administration changes the composition of bile and may dissolve gallstones. It is used as a cholagogue and choleretic.. ursodeoxycholic acid : A bile acid found in the bile of bears (Ursidae) as a conjugate with taurine. Used therapeutically, it prevents the synthesis and absorption of cholesterol and can lead to the dissolution of gallstones.. ursodeoxycholate : A bile acid anion that is the conjugate base of ursodeoxycholic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.	2.06	1	0	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
8-bromo cyclic adenosine monophosphate 8-Bromo Cyclic Adenosine Monophosphate: A long-acting derivative of cyclic AMP. It is an activator of cyclic AMP-dependent protein kinase, but resistant to degradation by cyclic AMP phosphodiesterase.. 8-Br-cAMP : A 3',5'-cyclic purine nucleotide that is 3',5'-cyclic AMP bearing an additional bromo substituent at position 8 on the adenine ring. An activator of cyclic AMP-dependent protein kinase, but resistant to degradation by cyclic AMP phosphodiesterase.	1.98	1	0	3',5'-cyclic purine nucleotide; adenyl ribonucleotide; organobromine compound	antidepressant; protein kinase agonist
alkenes [no description available]	4	4	0
glutamic acid Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.	7.34	54	0	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
glucaric acid Glucaric Acid: A sugar acid derived from D-glucose in which both the aldehydic carbon atom and the carbon atom bearing the primary hydroxyl group are oxidized to carboxylic acid groups.. D-glucaric acid : The D-enantiomer of glucaric acid.. glucaric acid : A hexaric acid derived by oxidation of sugar such as glucose with nitric acid.	2.21	1	0	glucaric acid	antineoplastic agent
azides Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.	2.44	2	0	pseudohalide anion	mitochondrial respiratory-chain inhibitor
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.	1.98	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.	3.2	5	0	sulfonium betaine	human metabolite
amineptin amineptin: used in treatment of neuroses with psychoasthenic, anxio-phobic & depressive manifestations; synonym S 1694 refers to HCl; structure. amineptine : A carbocyclic fatty acid that is 5-aminoheptanoic acid in which one of the hydrogens attached to the nitrogen is replaced by a 10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-yl group. A tricyclic antidepressant, it was never approved in the US and was withdrawn from the French market in 1999 due to concerns over abuse, dependence and severe acne.	1.97	1	0	amino acid; carbocyclic fatty acid; carbotricyclic compound; secondary amino compound	antidepressant; dopamine uptake inhibitor
acetylgalactosamine Acetylgalactosamine: The N-acetyl derivative of galactosamine.	2.05	1	0	N-acetyl-D-hexosamine; N-acetylgalactosamine	Escherichia coli metabolite; human metabolite; mouse metabolite
tobramycin Tobramycin: An aminoglycoside, broad-spectrum antibiotic produced by Streptomyces tenebrarius. It is effective against gram-negative bacteria, especially the PSEUDOMONAS species. It is a 10% component of the antibiotic complex, NEBRAMYCIN, produced by the same species.. tobramycin : A amino cyclitol glycoside that is kanamycin B lacking the 3-hydroxy substituent from the 2,6-diaminoglucose ring.	1.96	1	0	amino cyclitol glycoside	antibacterial agent; antimicrobial agent; toxin
paclitaxel Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).	3.19	5	0	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
amikacin Amikacin: A broad-spectrum antibiotic derived from KANAMYCIN. It is reno- and oto-toxic like the other aminoglycoside antibiotics.. amikacin : An amino cyclitol glycoside that is kanamycin A acylated at the N-1 position by a 4-amino-2-hydroxybutyryl group.	2.02	1	0	alpha-D-glucoside; amino cyclitol glycoside; aminoglycoside; carboxamide	antibacterial drug; antimicrobial agent; nephrotoxin
1,6-dinitropyrene [no description available]	1.96	1	0	pyrenes
1,8-dinitropyrene [no description available]	1.96	1	0	pyrenes
deoxynivalenol deoxynivalenol : A trichothecene mycotoxin produced by Fusarium to which wheat, barley, maize (corn) and their products are susceptible to contamination.	2.91	3	0	cyclic ketone; enone; primary alcohol; secondary alpha-hydroxy ketone; trichothecene; triol	mycotoxin
phosphopantothenic acid phosphopantothenic acid: RN given refers to (R)-isomer. (R)-4'-phosphopantothenic acid : An amidoalkyl phosphate that is the 4-phosphate derivative of (R)-pantothenic acid.	1.97	1	0	amidoalkyl phosphate	Escherichia coli metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
nitazoxanide nitazoxanide: a 5-nitrothiazolyl derivative used for a broad range of intestinal parasitic infections including CRYPTOSPORIDIUM and GIARDIA; it is a redox-active nitrothiazolyl-salicylamide prodrug	2.03	1	0	benzamides; carboxylic ester
2-amino-6-methyldipyrido(1,2-a-3',2'-d)imidazole 2-amino-6-methyldipyrido(1,2-a-3',2'-d)imidazole: structure	1.96	1	0	imidazopyridine
pimonidazole pimonidazole: structure given in first source	2.15	1	0
1,3-dinitropyrene [no description available]	2.37	2	0	pyrenes
lovastatin Lovastatin: A fungal metabolite isolated from cultures of Aspergillus terreus. The compound is a potent anticholesteremic agent. It inhibits 3-hydroxy-3-methylglutaryl coenzyme A reductase (HYDROXYMETHYLGLUTARYL COA REDUCTASES), which is the rate-limiting enzyme in cholesterol biosynthesis. It also stimulates the production of low-density lipoprotein receptors in the liver.. lovastatin : A fatty acid ester that is mevastatin carrying an additional methyl group on the carbobicyclic skeleton. It is used in as an anticholesteremic drug and has been found in fungal species such as Aspergillus terreus and Pleurotus ostreatus (oyster mushroom).	3.28	6	0	delta-lactone; fatty acid ester; hexahydronaphthalenes; polyketide; statin (naturally occurring)	anticholesteremic drug; antineoplastic agent; Aspergillus metabolite; prodrug
2-amino-3-methylimidazo(4,5-f)quinoline 2-amino-3-methylimidazo(4,5-f)quinoline: mutagen found in broiled food; RN given refers to parent cpd; structure given in first source; frequently abbreviated as IQ in the literature. 3-methyl-3H-imidazo[4,5-f]quinolin-2-amine : An imidazoquinoline that is 3H-imidazo[4,5-f]quinoline substituted by a methyl group at position 3 and an amino group at position 2.	1.96	1	0	imidazoquinoline	carcinogenic agent
quizalofop-ethyl quizalofop-ethyl: RN given refers to parent cpd. quizalofop-ethyl : A racemate coprising equimolar amounts of quizalofop-P-ethyl and its enantiomer, (S)-quizalofop-ethyl. A proherbicide for quizalofop.. ethyl 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoate : An ethyl ester resulting from the formal condensation of the carboxy group of 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoic acid with ethanol.	1.98	1	0	aromatic ether; ethyl ester; organochlorine compound; quinoxaline derivative
ethyl 2-(5-(4-chlorophenyl)pentyl)oxiran-2-carboxylate [no description available]	1.97	1	0
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.	2.01	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
quinpirole Quinpirole: A dopamine D2/D3 receptor agonist.. quinpirole : A pyrazoloquinoline that is (4aR,8aR)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrazolo[3,4-g]quinoline substituted by a propyl group at position 5. It acts as a dopamine agonist.	1.98	1	0	pyrazoloquinoline	dopamine agonist
pravastatin Pravastatin: An antilipemic fungal metabolite isolated from cultures of Nocardia autotrophica. It acts as a competitive inhibitor of HMG CoA reductase (HYDROXYMETHYLGLUTARYL COA REDUCTASES).. pravastatin : A carboxylic ester resulting from the formal condensation of (S)-2-methylbutyric acid with the hydroxy group adjacent to the ring junction of (3R,5R)-7-[(1S,2S,6S,8S,8aR)-6,8-dihydroxy-2-methyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid. Derived from microbial transformation of mevastatin, pravastatin is a reversible inhibitor of 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA). The sodium salt is used for lowering cholesterol and preventing cardiovascular disease. It is one of the lower potency statins, but has the advantage of fewer side effects compared with lovastatin and simvastatin.	2.01	1	0	3-hydroxy carboxylic acid; carbobicyclic compound; carboxylic ester; hydroxy monocarboxylic acid; secondary alcohol; statin (semi-synthetic)	anticholesteremic drug; environmental contaminant; metabolite; xenobiotic
mifepristone Mifepristone: A progestational and glucocorticoid hormone antagonist. Its inhibition of progesterone induces bleeding during the luteal phase and in early pregnancy by releasing endogenous prostaglandins from the endometrium or decidua. As a glucocorticoid receptor antagonist, the drug has been used to treat hypercortisolism in patients with nonpituitary CUSHING SYNDROME.	1.98	1	0	3-oxo-Delta(4) steroid; acetylenic compound; tertiary amino compound	abortifacient; contraceptive drug; hormone antagonist; synthetic oral contraceptive
ranolazine Ranolazine: An acetanilide and piperazine derivative that functions as a SODIUM CHANNEL BLOCKER and prevents the release of enzymes during MYOCARDIAL ISCHEMIA. It is used in the treatment of ANGINA PECTORIS.. N-(2,6-dimethylphenyl)-2-{4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl}acetamide : An aromatic amide obtained by formal condensation of the carboxy group of 2-{4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl}acetic acid with the amino group of 2,6-dimethylaniline.. ranolazine : A racemate comprising equal amounts of (R)- and (S)-ranolazine. Used for treatment of chronic angina.	1.99	1	0	aromatic amide; monocarboxylic acid amide; monomethoxybenzene; N-alkylpiperazine; secondary alcohol
adenosine quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit	4.17	5	0	adenosines; purines D-ribonucleoside	analgesic; anti-arrhythmia drug; fundamental metabolite; human metabolite; vasodilator agent
4-pentenoic acid 4-pentenoic acid: inhibitor of fatty acid oxidation; RN given refers to parent cpd. pent-4-enoic acid : A pentenoic acid having the double bond at position 4.	2.65	3	0	pentenoic acid
pyranine pyranine: structure	1.97	1	0	organic sodium salt	fluorochrome
vanadates Vanadates: Oxyvanadium ions in various states of oxidation. They act primarily as ion transport inhibitors due to their inhibition of Na(+)-, K(+)-, and Ca(+)-ATPase transport systems. They also have insulin-like action, positive inotropic action on cardiac ventricular muscle, and other metabolic effects.. vanadate(3-) : A vanadium oxoanion that is a trianion with formula VO4 in which the vanadium is in the +5 oxidation state and is attached to four oxygen atoms.	2.71	3	0	trivalent inorganic anion; vanadium oxoanion	EC 3.1.3.1 (alkaline phosphatase) inhibitor; EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; EC 3.1.3.41 (4-nitrophenylphosphatase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor
2-amino-3,4-dimethylimidazo(4,5-f)quinoline 2-amino-3,4-dimethylimidazo(4,5-f)quinoline: strong mutagens found in broiled food; structure given in first source	1.96	1	0	aminoquinoline
octyl glucoside octyl-beta-D-glucoside: RN given refers to (beta)-isomer. octyl beta-D-glucopyranoside : An beta-D-glucoside in which the anomeric hydrogen of beta-D-glucopyranose is substituted by an octyl group.	1.98	1	0	beta-D-glucoside	plant metabolite
trazodone hydrochloride Triticum: A plant genus of the family POACEAE that is the source of EDIBLE GRAIN. A hybrid with rye (SECALE CEREALE) is called TRITICALE. The seed is ground into FLOUR and used to make BREAD, and is the source of WHEAT GERM AGGLUTININS.. trazodone hydrochloride : A hydrochloride salt prepared from equimolar amounts of trazodone and hydrogen chloride.	2.41	2	0	hydrochloride	adrenergic antagonist; antidepressant; H1-receptor antagonist; sedative; serotonin uptake inhibitor
glucose, (beta-d)-isomer beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.	2.88	4	0	D-glucopyranose	epitope; mouse metabolite
mevastatin mevastatin: antifungal metabolite from Penicillium brevicopactum; potent inhibitory activity to sterol synthesis; structure. mevastatin : A carboxylic ester that is pravastatin that is lacking the allylic hydroxy group. A hydroxymethylglutaryl-CoA reductase inhibitor (statin) isolated from Penicillium citrinum and from Penicillium brevicompactum, its clinical use as a lipid-regulating drug ceased following reports of toxicity in animals.	1.97	1	0	2-pyranones; carboxylic ester; hexahydronaphthalenes; polyketide; statin (naturally occurring)	antifungal agent; apoptosis inducer; EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor; fungal metabolite; Penicillium metabolite
5-methylcytosine 5-Methylcytosine: A methylated nucleotide base found in eukaryotic DNA. In ANIMALS, the DNA METHYLATION of CYTOSINE to form 5-methylcytosine is found primarily in the palindromic sequence CpG. In PLANTS, the methylated sequence is CpNpGp, where N can be any base.. 5-methylcytosine : A pyrimidine that is a derivative of cytosine, having a methyl group at the 5-position.	2.15	1	0	methylcytosine; pyrimidines	human metabolite
thionine thionine: do not confuse with the thionins which is a class of polypeptides; RN above is for the chloride;. thionine : An organic chloride salt composed of 3,7-diaminophenothiazin-5-ium and chloride ions in a 1:1 ratio. A strongly metachromatic dye, useful for the staining of acid mucopolysaccharides. It is also a common nuclear stain and can be used for the demonstration of Nissl substance in nerve cells of the CNS.	2	1	0
epigallocatechin gallate epigallocatechin gallate: a steroid 5alpha-reductase inhibitor and antimutagen in green tea (Camellia sinensis). (-)-epigallocatechin 3-gallate : A gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (-)-epigallocatechin.	4.18	3	0	flavans; gallate ester; polyphenol	antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite
n-acetylaspartic acid N-acetyl-L-aspartic acid : An N-acyl-L-aspartic acid in which the acyl group is specified as acetyl.	3.89	11	0	N-acetyl-L-amino acid; N-acyl-L-aspartic acid	antioxidant; human metabolite; mouse metabolite; nutraceutical; rat metabolite
25-hydroxycholesterol [no description available]	2	1	0	25-hydroxy steroid; oxysterol	human metabolite
aica ribonucleotide AICA ribonucleotide: purine precursor that has antineoplastic activity. AICA ribonucleotide : A 1-(phosphoribosyl)imidazolecarboxamide that is acadesine in which the hydroxy group at the 5' position has been converted to its monophosphate derivative.	2.73	3	0	1-(phosphoribosyl)imidazolecarboxamide; aminoimidazole	cardiovascular drug; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
nile red nile red : An organic heterotetracyclic compound that is 5H-benzo[a]phenoxazin-5-one substituted at position 9 by a diethylamino group.	2.11	1	0	aromatic amine; cyclic ketone; organic heterotetracyclic compound; tertiary amino compound	fluorochrome; histological dye
fructose-1-phosphate fructose-1-phosphate: RN in Chemline for alpha-D-fructopyranose-cpd:126-25-0; RN given refers to (D)-isomer. D-fructose 1-phosphate : The D-enantiomer of fructose 1-phosphate.. keto-D-fructose 1-phosphate : The open chain form of D-fructose 1-phosphate.	2.25	1	0	D-fructose 1-phosphate
n-acetylserine acetyl-L-serine : An acetyl-amino acid in which the amino acid specified is L-serine.. N-acetyl-L-serine : An N-acetyl-L-amino acid in which the amino acid specified is L-serine. Metabolite observed in cancer metabolism.	1.96	1	0	acetyl-L-serine; N-acetyl-L-amino acid	human metabolite
n(4)-acetylsulfamethoxazole N-acetylsulfamethoxazole : A sulfonamide compound having a 4-acetamidophenyl group attached to the sulfur atom and a 1,2-oxazol-3-yl group attached to the nitrogen atom.	2.38	2	0	isoxazoles; sulfonamide	drug metabolite; marine xenobiotic metabolite
glutathione disulfide Glutathione Disulfide: A GLUTATHIONE dimer formed by a disulfide bond between the cysteine sulfhydryl side chains during the course of being oxidized.	2.4	2	0	glutathione derivative; organic disulfide	Escherichia coli metabolite; mouse metabolite
baccatin iii [no description available]	2.8	3	0	acetate ester; benzoate ester; tetracyclic diterpenoid	plant metabolite
cephalosporin c cephalosporin C: RN given refers to parent cpd; structure in Merck, 9th ed, #1937. cephalosporin C : A cephalosporin antibiotic carrying a 3-acetoxymethyl substituent and a 6-oxo-N(6)-L-lysino group at position 7.	2.93	4	0	cephalosporin	fungal metabolite
lathosterol lathosterol: RN given refers to (3beta,5alpha)-isomer. 5alpha-cholest-7-en-3beta-ol : A cholestanoid that is (5alpha)-cholest-7-ene substituted by a beta-hydroxy group at position 3.	2.01	1	0	3beta-sterol; C27-steroid; cholestanoid; Delta(7)-sterol	human metabolite; mouse metabolite
web 2086 WEB 2086: structure given in first source; PAF antagonist	1.98	1	0	organonitrogen heterocyclic compound; organosulfur heterocyclic compound
methacycline [no description available]	2.15	1	0	1,2-diglyceride
peroxyformic acid peroxyformic acid: structure	2.37	2	0
cetiedil cetiedil: RN given refers to parent cpd; structure	1.99	1	0	azepanes
1,7-phenanthroline [no description available]	2.39	2	0	phenanthroline
triazoles Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.	2.42	2	0	1,2,3-triazole
3-fluoropyruvate 3-fluoropyruvate: a substrate for E coli pyruvate dehydrogenase; structure; RN given refers to parent cpd. 3-fluoropyruvic acid : A pyruvic acid derivative having a 3-fluoro substituent.. 3-fluoropyruvate : The anion of 3-fluoropyruvic acid.	1.99	1	0	2-oxo monocarboxylic acid; organofluorine compound
formamidine formamidine: RN given refers to parent compound. formamidine : The smallest member of the class of carboxamidines being formic acid with the O and OH groups from the carboxy function replaced by NH and NH2 groups respectively. The parent of the class of formamidines.	1.98	1	0	carboxamidine; formamidines; one-carbon compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor
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.	5.11	13	0	3-hydroxy monocarboxylic acid; omega-hydroxy-short-chain fatty acid	Escherichia coli metabolite; human metabolite
triheptanoin [no description available]	5.64	6	0
3-propylphenol 3-propylphenol: insect bait; RN from File CHEMID	2.25	1	0
beta-hydroxyisovaleric acid 3-hydroxyisovaleric acid : A 3-hydroxy monocarboxylic acid that is isovaleric acid substituted at position 3 by a hydroxy group. Used as indicator of biotin deficiency.	1.96	1	0	3-hydroxy monocarboxylic acid	human metabolite
indole-3-carboxylic acid indole-3-carboxylic acid : An indole-3-carboxylic acid carrying a carboxy group at position 3.	2.15	1	0	indol-3-yl carboxylic acid	bacterial metabolite; human metabolite
1,3-dibromo-2-propanone [no description available]	1.99	1	0
n-acetyltryptamine N-acetyltryptamine: antagonizes the melatonin-induced inhibition of dopamine release from retina; RN given refers to parent cpd. N-acetyltryptamine : A tryptamine compound having an acetyl substituent attached to the side-chain amino function.	2	1	0	acetamides; indoles
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.	6.07	11	1	N-acetyl-L-amino acid; N-acyl-L-glutamic acid	human metabolite; Saccharomyces cerevisiae metabolite
tyloxapol tyloxapol: non-ionic detergent with surface-active properties; incompatible with metals; surfactant also used in inhalation therapy; N1 is from CA Vol 90 Form Index; N1 in Chemline is same as synonym 8. tyloxapol : A polymeric compound resulting from the reaction of 4-(1,1,3,3-tetramethylbutyl)phenol with formaldehyde to give a chain in which 6-8 molecules are linked together by CH2 groups ortho to the phenolic hydroxy groups, which have then undergone reaction with oxirane to give polyoxyethyleneoxy moieties, Ar(OCH2CH2)xOH, where x = 8-10. A nonionic liquic polymer, it inhibits lipoprotein lipase and hence clearance of triglyceride from the plasma, so is used to induce hyperlipidaemia in test animals. Also used as a surfactant to aid liquefaction and removal of mucus- and pus-containing bronchopulmonary secretions.	1.96	1	0
2-tetradecylglycidic acid 2-tetradecylglycidic acid: structure	2.38	2	0
fagomine fagomine: structure in first source	1.99	1	0	piperidines
tetrandrine tetrandrine: a bisbenzylisoquinoline that exhibits antifibrogenic activity	2.41	1	0	bisbenzylisoquinoline alkaloid; isoquinolines
beta-amyrin beta-amyrin: alpha-amyrin is also available; a 5 ring triterpene derived from oleanane that differs from alpha-amyrin in having the 29-carbon at the 20 position; RN given refers to (3 beta)-isomer. beta-amyrin : A pentacyclic triterpenoid that is oleanane substituted at the 3beta-position by a hydroxy group and containing a double bond between positions 12 and 13. It is one of the most commonly occurring triterpenoids in higher plants.	2.21	1	0	pentacyclic triterpenoid; secondary alcohol	Aspergillus metabolite; plant metabolite
calpeptin [no description available]	2.1	1	0	amino acid amide
tetracenomycin c tetracenomycin C: chemically related to tetracyclines & anthracyclinones but not a member of either group; produced by Streptomyces glaucescens, strain Tu 49	2.4	2	0	methyl ester; tertiary alpha-hydroxy ketone; tetracenomycin
pentafluorobenzyl bromide pentafluorobenzyl bromide : A member of the class benzyl bromides that is benzyl bromide in which the hydrogens at positions 2, 3, 4, 5 and 6 of the phenyl ring are replaced by fluoro groups. It is a versatile derivatization agent in chromatography and mass spectrometry.	1.98	1	0	benzyl bromides; fluorobenzenes
n-acetylhistidine N-acetylhistidine: RN given refers to (L)-isomer. N-acetylhistidine : A histidine derivative that is histidine in which one of the hydrogens of the alpha-amino group is substituted by an acetyl group.. N-acetyl-L-histidine : A histidine derivative that is L-histidine having an acetyl substituent on the alpha-nitrogen.	2.1	1	0	L-histidine derivative; N-acetyl-L-amino acid; N-acetylhistidine	animal metabolite
rosiglitazone [no description available]	2.52	2	0	aminopyridine; thiazolidinediones	EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor; ferroptosis inhibitor; insulin-sensitizing drug
n-hydroxy-4-aminobiphenyl [no description available]	2.66	3	0	aminobiphenyl; N-substituted amine	carcinogenic agent; human xenobiotic metabolite
tebuconazole Lynx: A genus in the family FELIDAE comprising felines with long legs, ear tufts, and a short tail.. 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol : A tertiary alcohol that is pentan-3-ol substituted by a 4-chlorophenyl, methyl, methyl, and a 1H-1,2,4-triazol-1-ylmethyl at positions 1, 4, 4 and 3 respectively.. tebuconazole : A racemate composed of equimolar amounts of (R)- and (S)-tebuconazole. A fungicide effective against various smut and bunt diseases in cereals and other field crops.	2.11	1	0	monochlorobenzenes; tertiary alcohol; triazoles
stearoyl alpha-lysolecithin stearoyl alpha-lysolecithin: RN given refers to cpd without isomeric designation. 2-lysophosphatidylcholine : Any member of the class of lysophosphatidylcholines which has a free hydroxy group at the 2-position of the glycerol moiety.	1.96	1	0
coenzyme a [no description available]	11.95	404	1	adenosine 3',5'-bisphosphate	coenzyme; Escherichia coli metabolite; mouse metabolite
slaframine slaframine: biosynthesized in fungus, Rhizoctonia leguminicola; causes excessive salivation in animals; RN given is for parent cpd. slaframine : An indolizidine alkaloid that is octahydroindolizine substituted by an amino group at position 6 and an acetyloxy group at position 1.	1.95	1	0
tretazicar tretazicar: minor descriptor (75-84); on-line & Index Medicus search AZIRIDINES (75-84)	1.97	1	0
nicotine (S)-nicotine : A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has S-configuration. The naturally occurring and most active enantiomer of nicotine, isolated from Nicotiana tabacum.	2.73	3	0	3-(1-methylpyrrolidin-2-yl)pyridine	anxiolytic drug; biomarker; immunomodulator; mitogen; neurotoxin; nicotinic acetylcholine receptor agonist; peripheral nervous system drug; phytogenic insecticide; plant metabolite; psychotropic drug; teratogenic agent; xenobiotic
terreic acid terreic acid: antibiotic metabolite of mold Aspergillus terreus; RN given refers to (1R)-isomer; structure	2.13	1	0	arene epoxide; diketone; monohydroxy-1,4-benzoquinones; tertiary alpha-hydroxy ketone	antibacterial agent; antineoplastic agent; Aspergillus metabolite; EC 2.3.1.* (acyltransferase transferring other than amino-acyl group) inhibitor; EC 2.5.1.7 (UDP-N-acetylglucosamine 1-carboxyvinyltransferase) inhibitor; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; mycotoxin
17-alpha-hydroxypregnenolone 17-alpha-Hydroxypregnenolone: A 21-carbon steroid that is converted from PREGNENOLONE by STEROID 17-ALPHA-HYDROXYLASE. It is an intermediate in the delta-5 pathway of biosynthesis of GONADAL STEROID HORMONES and the adrenal CORTICOSTEROIDS.. 17alpha-hydroxypregnenolone : A hydroxypregnenolone carrying an alpha-hydroxy group at position 17.	1.96	1	0	17alpha-hydroxy-C21-steroid; 17alpha-hydroxy steroid; 3beta-hydroxy-Delta(5)-steroid; hydroxypregnenolone; tertiary alpha-hydroxy ketone	human metabolite; mouse metabolite
6-phosphogluconic acid gluconic acid-6-phosphate: structure. 6-phospho-D-gluconate : A monocarboxylic acid anion resulting from the removal of a proton from the carboxy group of 6-phospho-D-gluconic acid.. 6-phospho-D-gluconic acid : A gluconic acid phosphate having the phosphate group at the 6-position. It is an intermediate in the pentose phosphate pathway.	2.43	2	0	gluconic acid phosphate	fundamental metabolite
succinyl-coenzyme a [no description available]	6.07	22	0	omega-carboxyacyl-CoA	Escherichia coli metabolite; inhibitor; mouse metabolite
4-hydroxyphenylglycine 4-hydroxyphenylglycine : A glycine molecule carrying a 4-hydroxyphenyl substituent.	1.97	1	0	hydroxy-amino acid	bacterial metabolite
acetoacetyl coa [no description available]	7.51	55	0	3-oxo-fatty acyl-CoA	Escherichia coli metabolite; mouse metabolite
n(6)-(delta(2)-isopentenyl)adenine N(6)-dimethylallyladenine : A 6-isopentenylaminopurine in which has the isopentenyl double bond is located between the 2 and 3 positions of the isopentenyl group.	3.05	1	0	6-isopentenylaminopurine	cytokinin
propionyl-coenzyme a propionyl-coenzyme A: RN given refers to parent cpd	6.26	46	0	acyl-CoA	Escherichia coli metabolite; metabolite; mouse metabolite
3-chlorolactate 3-chlorolactate: RN given refers to parent cpd without isomeric designation. 3-chlorolactic acid : A 2-hydroxy monocarboxylic acid that is lactic acid in which one of the methyl hydrogens is replaced by a chloro group.	1.97	1	0	2-hydroxy monocarboxylic acid; organochlorine compound
firefly luciferin Firefly Luciferin: A benzothaizole which is oxidized by LUCIFERASES, FIREFLY to cause emission of light (LUMINESCENCE).. Photinus luciferin : A 1,3-thiazolemonocarboxylic acid consisting of 3,5-dihydrothiophene-4-carboxylic acid having a 6-hydroxybenzothiazol-2-yl group at the 2-position.	2.02	1	0	1,3-thiazolemonocarboxylic acid; benzothiazoles; imidothioate	luciferin
glycidyl nitrate glycidyl nitrate: a nitric oxide donor; structure in first source. peptidoglycan : A peptidoglycosaminoglycan formed by alternating residues of beta-(1->4)-linked N-acetylglucosamine and N-acetylmuramic acid {2-amino-3-O-[(S)-1-carboxyethyl]-2-deoxy-D-glucose} residues. Attached to the carboxy group of the muramic acid is a peptide chain of three to five amino acids.	2.54	2	0
dodecyl glucoside dodecyl glucoside: RN given refers to (beta-D)-isomer	1.98	1	0
glucuronic acid Glucuronic Acid: A sugar acid formed by the oxidation of the C-6 carbon of GLUCOSE. In addition to being a key intermediate metabolite of the uronic acid pathway, glucuronic acid also plays a role in the detoxification of certain drugs and toxins by conjugating with them to form GLUCURONIDES.. D-glucuronic acid : The D-enantiomer of glucuronic acid.. D-glucopyranuronic acid : A D-glucuronic acid in cyclic pyranose form.	2.97	4	0	D-glucuronic acid	algal metabolite
poly-o-acetylserine O-acetylserine: RN given refers to (DL)-isomer. O-acetyl-L-serine : An acetyl-L-serine where the acetyl group is attached to the side-chain oxygen. It is an intermediate in the biosynthesis of the amino acid cysteine in bacteria.	2.13	1	0	acetate ester; acetyl-L-serine; amino acid zwitterion	bacterial metabolite; Saccharomyces cerevisiae metabolite
saframycin a saframycin A: structure given in first source	2.01	1	0
2-amino-4-phenylbutyric acid 2-amino-4-phenylbutanoic acid: structure in first source	1.98	1	0
cobalt Cobalt: A trace element that is a component of vitamin B12. It has the atomic symbol Co, atomic number 27, and atomic weight 58.93. It is used in nuclear weapons, alloys, and pigments. Deficiency in animals leads to anemia; its excess in humans can lead to erythrocytosis.. cobalt(1+) : A monovalent inorganic cation obtained from cobalt.. cobalt atom : A cobalt group element atom that has atomic number 27.	7.92	4	0	cobalt group element atom; metal allergen	micronutrient
s-nitrosoglutathione [no description available]	2.41	2	0	glutathione derivative; nitrosothio compound	bronchodilator agent; nitric oxide donor; platelet aggregation inhibitor; signalling molecule
2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine: directly acting genotoxic metabolite of 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine. N-hydroxy-PhIP : An imidazopyridine that is 1H--imidazo[4,5-b]pyridine which is substituted at positions 1, 2, and 6 by methyl, hydoxyamino, and phenyl groups, respectively. The active metabolite of the dietary carcinogen PhIP.	2.38	2	0	hydroxylamine; imidazopyridine	carcinogenic agent; genotoxin; human xenobiotic metabolite; mouse metabolite; mutagen; neurotoxin; rat metabolite
2-hydroxyamino-6-methyldipyrido(1,2-a-3',2'-d)imidazole 2-hydroxyamino-6-methyldipyrido(1,2-a-3',2'-d)imidazole: structure given in first source	2.37	2	0
fructose 2,6-diphosphate fructose 2,6-diphosphate: phosphofructokinase activator synthesized via Mg-ATP & fructose-6-P. beta-D-fructofuranose 2,6-bisphosphate : A D-fructofuranose 2,6-bisphosphate with a beta-configuration at the anomeric centre.	1.98	1	0	D-fructofuranose 2,6-bisphosphate	human metabolite; mouse metabolite
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).	2.38	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	2.67	3	0	carbonyl compound
3-((3-cholamidopropyl)dimethylammonium)-1-propanesulfonate 3-((3-cholamidopropyl)dimethylammonium)-1-propanesulfonate: a surfactant; structure given in first source	2.42	2	0	1,1-diunsubstituted alkanesulfonate
propionylcarnitine propionylcarnitine: RN given refers to cpd without isomeric designation	2.39	2	0	O-acylcarnitine	analgesic; antirheumatic drug; cardiotonic drug; human metabolite; peripheral nervous system drug
beta-hydroxyvaleric acid 3-hydroxypentanoic acid : A short-chain fatty acid that is valeric acid in which one of the methylene hydrogens at position 3 has been replaced by a hydroxy group.	2.72	3	0	3-hydroxy fatty acid; ketone body; short-chain fatty acid
s-benzyl-n-acetyl-l-cysteine S-benzyl-N-acetyl-L-cysteine: RN given refers to (L)-isomer. N-acetyl-S-benzyl-L-cysteine : The S-benzyl derivative of N-acetyl-L-cysteine.	1.98	1	0	organic sulfide; S-substituted N-acetyl-L-cysteine	human urinary metabolite; rat metabolite
triptolide [no description available]	2.21	1	0	diterpenoid; epoxide; gamma-lactam; organic heteroheptacyclic compound	antispermatogenic agent; plant metabolite
ecteinascidin 743 [no description available]	2.01	1	0	acetate ester; azaspiro compound; bridged compound; hemiaminal; isoquinoline alkaloid; lactone; organic heteropolycyclic compound; organic sulfide; oxaspiro compound; polyphenol; tertiary amino compound	alkylating agent; angiogenesis modulating agent; anti-inflammatory agent; antineoplastic agent; marine metabolite
1-hexadecyl-2-acetyl-glycero-3-phosphocholine Platelet Activating Factor: A phospholipid derivative formed by PLATELETS; BASOPHILS; NEUTROPHILS; MONOCYTES; and MACROPHAGES. It is a potent platelet aggregating agent and inducer of systemic anaphylactic symptoms, including HYPOTENSION; THROMBOCYTOPENIA; NEUTROPENIA; and BRONCHOCONSTRICTION.. 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine : A 2-acetyl-1-alkyl-sn-glycero-3-phosphocholine betaine which has hexadecyl as the alkyl group. PAF is a potent phospholipid activator and mediator of many leukocyte functions, including platelet aggregation, inflammation, and anaphylaxis.	4.54	25	0	2-acetyl-1-alkyl-sn-glycero-3-phosphocholine	antihypertensive agent; beta-adrenergic antagonist; bronchoconstrictor agent; hematologic agent; vasodilator agent
n-hydroxy-3,2'-dimethyl-4-aminobiphenyl [no description available]	7.66	3	0
deoxyglucose Deoxyglucose: 2-Deoxy-D-arabino-hexose. An antimetabolite of glucose with antiviral activity.. deoxyglucose : A deoxyhexose comprising glucose having at least one hydroxy group replaced by hydrogen.	2.94	4	0
valerates Valerates: Derivatives of valeric acid, including its salts and esters.	3.75	11	0	short-chain fatty acid anion; straight-chain saturated fatty acid anion	plant metabolite
1-(carboxymethylthio)tetradecane 1-(carboxymethylthio)tetradecane: structure given in first source; alkylthio acetic acid, non-beta-oxidizable	1.98	1	0	straight-chain fatty acid
1,2-dimyristoylphosphatidylethanolamine [no description available]	2.48	2	0
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
2-aminobicyclo(2,2,1)heptane-2-carboxylic acid 2-aminobicyclo(2,2,1)heptane-2-carboxylic acid: amino acid analog; releases insulin; RN given refers to unlabeled cpd without isomeric designation	2.02	1	0	monoterpenoid
3-mercaptopicolinic acid 3-mercaptopicolinic acid: gluconeogenesis inhibitor; may also inhibit ATP-dependentphosphoenolpyruvate carboxykinase	1.97	1	0
afdx 384 [no description available]	2.02	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.	6.02	45	0	fatty acid anion 8:0; straight-chain saturated fatty acid anion	human metabolite; Saccharomyces cerevisiae metabolite
n-acetyltyramine N-acetyltyramine: structure given in first source. N-acetyltyramine : A member of the class of tyramines that is tyramine in which one of the hydrogens of the amino group is replaced by an acetyl group.	2.1	1	0	acetamides; tyramines	animal metabolite; Aspergillus metabolite; bacterial metabolite; marine metabolite; quorum sensing inhibitor
carglumic acid carglumic acid: carglumic acid could be helpful in lowering plasma ammonia levels over 400 micromol/L more rapidly. carglumic acid : A urea that is the N-carbamoyl derivative of L-glutamic acid. An orphan drug used to treat a deficiency in the enzyme N-acetylglutamate synthase, which leads to acute hyperammonaemia.	4.34	1	1	N-acyl-L-glutamic acid; ureas	carbamylphosphate synthetase I activator; orphan drug
angustmycin a angustmycin A: structure; from Streptomyces hygroscopicus; inhibits GMP synthesis	1.96	1	0	6-aminopurines
emeriamine emeriamine: derived from fungal metabolite emericedin; structure given in first source	1.98	1	0
n-(4-(7-diethylamino-4-methylcoumarin-3-yl)phenyl)maleimide N-(4-(7-diethylamino-4-methylcoumarin-3-yl)phenyl)maleimide: structure given in first source. 7-diethylamino-3-(4-maleimidophenyl)-4-methylcoumarin : A member of the class of coumarins that is 2H-chromen-2-one substituted by 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)phenyl, methyl, and diethylamino groups at positions 3, 4 and 7, respectively. It is a thiol-reactive fluorescent dye.	2.08	1	0	benzenes; coumarins; maleimides; tertiary amino compound	fluorescent dye
phytosphingosine phytosphingosine: differ with an additional hydroxyl at C-4 & no double bond between C-4 & C-5	2.13	1	0	amino alcohol; sphingoid; triol	mouse metabolite; Saccharomyces cerevisiae metabolite
flavin semiquinone flavin semiquinone: chromophore found in methanol oxidase	1.99	1	0
benzoyl-coenzyme a benzoyl-coenzyme A: RN given refers to unlabeled cpd	2.91	4	0
butyryl-coenzyme a [no description available]	5.45	20	0	butanoyl-CoAs	Escherichia coli metabolite; mouse metabolite
octanoyl-coenzyme a [no description available]	2.91	4	0
celastrol [no description available]	2.21	1	0	monocarboxylic acid; pentacyclic triterpenoid	anti-inflammatory drug; antineoplastic agent; antioxidant; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; Hsp90 inhibitor; metabolite
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
n(8)-acetylspermidine N(8)-acetylspermidine : An acetylspermidine that is 1,8-diamino-4-azaoctane in which one of the hydrogens of the amino group attached to C-8 is replaced by an acetyl group.	1.99	1	0	acetylspermidine	Escherichia coli metabolite; human metabolite
5,5'-bis(8-(phenylamino)-1-naphthalenesulfonate) [no description available]	1.99	1	0
3-(2,2,2-trimethylhydrazine)propionate 3-(2,2,2-trimethylhydrazine)propionate: structural analog of gamma-butyrobetaine, also of carnitine; antianginal compound; MET-88 is dihydrate; structure given in first source. meldonium : An ammonium betaine that is beta-alaninate in which one of the amino hydrogens is replaced by a trimethylamino group. A clinically used cardioprotective drug that is used for treatment of heart failure, myocardial infarction, arrhythmia, atherosclerosis and diabetes.	2.05	1	0	ammonium betaine	cardioprotective agent; EC 1.14.11.1 (gamma-butyrobetaine dioxygenase) inhibitor; neuroprotective agent
1-((3,5-dichloro)-2,6-dihydroxy-4-methoxyphenyl)-1-hexanone 1-((3,5-dichloro)-2,6-dihydroxy-4-methoxyphenyl)-1-hexanone: structure given in first source. 1-(3,5-dichloro-2,6-dihydroxy-4-methoxyphenyl)hexan-1-one : A differentiation-inducing factor that is hexaphenone bearing two chloro substituents at positions 3 and 5, two hydroxy substituents at positions 2 and 6 as well as a single methoxy substituent at position 4. A secreted, chlorinated molecule that controls cell fate during development of Dictyostelium cells.	2.65	3	0	dichlorobenzene; differentiation-inducing factor; monomethoxybenzene; resorcinols	eukaryotic metabolite; signalling molecule
hydroxycitric acid hydroxycitric acid: RN given refers to cpd without isomeric designation; structure	3.68	10	0	carbonyl compound
phosphohistidine phosphohistidine: RN given refers to N-phosphono-L-histidine	2.15	1	0
dehydroalanine 2-ammonioprop-2-enoate : An amino acid zwitterion resulting from a transfer of a proton from the carboxy group to the amino group of 2-aminoacrylic acid.. 2-aminoacrylic acid : A 2,3-dehydroamino acid that is alanine which has been dehydrogenated to introduce a double bond between positions 2 and 3.	2.15	1	0	2,3-dehydroamino acid; alpha,beta-unsaturated monocarboxylic acid; amino acid zwitterion; enamine; non-proteinogenic alpha-amino acid	alkylating agent; human metabolite; mouse metabolite
glutamate-1-semialdehyde (S)-4-amino-5-oxopentanoic acid : A 5-oxo monocarboxylic acid that is 5-oxopentanoic acid substituted by an amino group at position 4 (the 4S-stereoisomer).	2.02	1	0	5-oxo monocarboxylic acid; amino acid zwitterion; gamma-amino acid; glutamic semialdehyde	Escherichia coli metabolite
dexpanthenol dexpanthenol: The alcohol of pantothenic acid	3.7	1	0	amino alcohol; monocarboxylic acid amide	cholinergic drug; provitamin
castasterone castasterone: a brassinosteroid; RN refers to ((2alpha,3alpha,5alpha,22R,23R,24S)-isomer; structure in first source	2.25	1	0	22-hydroxy steroid; 23-hydroxy steroid; 2alpha-hydroxy steroid; 3alpha-hydroxy steroid; 6-oxo steroid; brassinosteroid	plant growth stimulator
carbapenems [no description available]	2.02	1	0
2,3-diacetamido-2,3-dideoxymannuronic acid 2,3-diacetamido-2,3-dideoxymannuronic acid: from Pseudomonas aeruginosa lipopolysaccharide	2.05	1	0
xylose xylopyranose: structure in first source	4.27	5	0	D-xylose
beta-lactams 2-azetidinone: structure in first source. azetidin-2-one : An unsubstituted beta-lactam compound.. beta-lactam : A lactam in which the amide bond is contained within a four-membered ring, which includes the amide nitrogen and the carbonyl carbon.	2.01	1	0	beta-lactam antibiotic allergen; beta-lactam
proline Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.	2.95	4	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
cucurbitaceae Cucurbitaceae: The gourd plant family of the order Violales, subclass Dilleniidae, class Magnoliopsida. It is sometimes placed in its own order, Cucurbitales. 'Melon' generally refers to CUCUMIS; CITRULLUS; or MOMORDICA.	2	1	0
docetaxel anhydrous Docetaxel: A semisynthetic analog of PACLITAXEL used in the treatment of locally advanced or metastatic BREAST NEOPLASMS and NON-SMALL CELL LUNG CANCER.. docetaxel anhydrous : A tetracyclic diterpenoid that is paclitaxel with the N-benzyloxycarbonyl group replaced by N-tert-butoxycarbonyl, and the acetoxy group at position 10 replaced by a hydroxy group.	2.17	1	0	secondary alpha-hydroxy ketone; tetracyclic diterpenoid	antimalarial; antineoplastic agent; photosensitizing agent
ribulose ribulose: 5-carbon keto sugar; minor descriptor (75-85); on-line & Index Medicus search PENTOSES (75-85); RN given refers to (erythro)-isomer	2.31	1	0	ribulose	Escherichia coli metabolite; human metabolite
3-hydroxyhexanoic acid 3-hydroxyhexanoic acid: abnormal metabolite in urine & serum of diabetic ketoacidotic patients	2.11	1	0	3-hydroxy monocarboxylic acid
12-phenyllauric acid [no description available]	1.97	1	0
(2-benzoylethyl)trimethylammonium (2-benzoylethyl)trimethylammonium: RN given refers to parent cpd	2.11	1	0
10-deacetylbaccatine iii 10-deacetylbaccatine III: structure given in first source	2.49	2	0	secondary alpha-hydroxy ketone; tetracyclic diterpenoid
adenosine 3'-phosphate-5'-phosphate adenosine 3',5'-bismonophosphate : An adenosine bisphosphate having two monophosphate groups at the 3'- and 5'-positions.	1.98	1	0	adenosine bisphosphate	Escherichia coli metabolite; mouse metabolite
sulfoacetaldehyde [no description available]	2.05	1	0	alpha-CH2-containing aldehyde; organosulfonic acid
alpha-methyl-beta-hydroxybutyrate 2-methyl-3-hydroxybutyric acid: metabolite from isoleucine; RN given refers to cpd without isomeric designation. 3-hydroxy-2-methylbutanoic acid : A 3-hydroxy monocarboxylic acid that is butyric acid which is substituted by a methyl group and a hydroxy group at positions 2 and 3, respectively.	1.96	1	0	3-hydroxy monocarboxylic acid
saccharopine L-saccharopine : The N(6)-(1,3-dicarboxypropan-1-yl) derivative of L-lysine.	3.35	1	0	amino acid opine; L-lysine derivative	human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
dimethylsulfonioacetate dimethylthetin: synthetic analog of glycine betaine; structure in first source	2.13	1	0	sulfonium betaine
1,10-bis(carboxymethylthiodecane) 1,10-bis(carboxymethylthiodecane): structure given in first source; alkylthio dicarboxylic acid; non-beta-oxidizable & non-omega-oxidizable	1.98	1	0
methylenecyclopropyl acetyl-coa methylenecyclopropyl acetyl-CoA: metabolite of hypoglycin	3.08	5	0
sedoheptulose 7-phosphate sedoheptulose 7-phosphate : A ketoheptose phosphate consisting of sedoheptulose having a phosphate group at the 7-position. It is an intermediate metabolite in the pentose phosphate pathway.	2.05	1	0	ketoheptose phosphate; sedoheptulose derivative	Escherichia coli metabolite; human metabolite; mouse metabolite
cysteinesulfenic acid cysteinesulfenic acid: a protein-sulfenic acid with diverse roles in enzyme catalysis, redox regulation and signal transduction. S-oxy-L-cysteine : A cysteine derivative consiting of L-cysteine carrying an S-oxy-substituent.. S-hydroxy-L-cysteine : A cysteine derivative consisting of L-cysteine carrying an S-hydroxy-substituent.	2.01	1	0	L-cysteine derivative; non-proteinogenic L-alpha-amino acid
n1'-carboxybiotin N1'-carboxybiotin: RN & N1 from 9th CI Form Index; RN given refers to (3aS-(3a alpha,4 beta,6a alpha))-isomer	4.33	6	0
paromomycin Paromomycin: An aminoglycoside antibacterial and antiprotozoal agent produced by species of STREPTOMYCES.. paromomycin : An amino cyclitol glycoside that is the 1-O-(2-amino-2-deoxy-alpha-D-glucopyranoside) and the 3-O-(2,6-diamino-2,6-dideoxy-beta-L-idopyranosyl)-beta-D-ribofuranoside of 4,6-diamino-2,3-dihydroxycyclohexane (the 1R,2R,3S,4R,6S diastereoisomer). It is obtained from various Streptomyces species. A broad-spectrum antibiotic, it is used (generally as the sulfate salt) for the treatment of acute and chronic intestinal protozoal infections, but is not effective for extraintestinal protozoal infections. It is also used as a therapeutic against visceral leishmaniasis.	2.39	2	0	amino cyclitol glycoside; aminoglycoside antibiotic	anthelminthic drug; antibacterial drug; antiparasitic agent; antiprotozoal drug
phenylacetyl-coenzyme a phenylacetyl-CoA : An acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of phenylacetic acid.	5.88	31	0	acyl-CoA	Escherichia coli metabolite; metabolite; mouse metabolite
anacardic acid anacardic acid: isolated from Anacardium occidentale; monophenol monooxygenase inhibitor. anacardic acid : A hydroxybenzoic acid that is salicylic acid substituted by a pentadecyl group at position 6. It is a major component of cashew nut shell liquid and exhibits an extensive range of bioactivities.	4.18	3	0	hydroxy monocarboxylic acid; hydroxybenzoic acid	anti-inflammatory agent; antibacterial agent; anticoronaviral agent; apoptosis inducer; EC 2.3.1.48 (histone acetyltransferase) inhibitor; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; neuroprotective agent; plant metabolite
fusigen fusigen: a siderochrome found in Aspergillus; structure	2.06	1	0
4-hydroxybenzoyl-coenzyme a 4-hydroxybenzoyl-CoA : A hydroxybenzoyl-CoA that is the S-(4-hydroxybenzoyl) derivative of coenzyme A.	2.04	1	0	hydroxybenzoyl-CoA
rabelomycin rabelomycin: structure	2.43	2	0
2-naphthoylethyltrimethylammonium 2-naphthoylethyltrimethylammonium: structure given in first source; RN given refers to iodide	1.97	1	0
biotin vitamin B7 : Any member of a group of vitamers that belong to the chemical structural class called biotins that exhibit biological activity against vitamin B7 deficiency. Vitamin B7 deficiency is very rare in individuals who take a normal balanced diet. Foods rich in biotin are egg yolk, liver, cereals, vegetables (spinach, mushrooms) and rice. Symptoms associated with vitamin B7 deficiency include thinning hair, scaly skin rashes around eyes, nose and mouth, and brittle nails. The vitamers include biotin and its ionized and salt forms.	12.33	46	0	biotins; vitamin B7	coenzyme; cofactor; Escherichia coli metabolite; fundamental metabolite; human metabolite; mouse metabolite; nutraceutical; prosthetic group; Saccharomyces cerevisiae metabolite
thiamine thiothiazolone pyrophosphate thiamine thiothiazolone pyrophosphate: thiamin pyrophosphate with its thiazole ring altered to thiothiazolone	1.99	1	0
atropine tropan-3alpha-yl 3-hydroxy-2-phenylpropanoate : A tropane alkaloid that is (1R,5)-8-methyl-8-azabicyclo[3.2.1]octane substituted by a (3-hydroxy-2-phenylpropanoyl)oxy group at position 3.	3.06	1	0
lignin Lignin: The most abundant natural aromatic organic polymer found in all vascular plants. Lignin together with cellulose and hemicellulose are the major cell wall components of the fibers of all wood and grass species. Lignin is composed of coniferyl, p-coumaryl, and sinapyl alcohols in varying ratios in different plant species. (From Merck Index, 11th ed). lignin : A polyphenylpropanoid derived from three monolignol monomers: trans-p-coumaryl alcohol, coniferol and trans-sinapyl alcohol. There is extensive cross-linking and no defined primary structure.	2.91	3	0
aceglutamide N-acetyl-L-glutamine : An N(2)-acetylglutamine that has L-configuration.	2.21	1	0	N-acetyl-L-amino acid; N(2)-acetylglutamine; N(2)-acyl-L-glutamine	human metabolite
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.	2.11	1	0	aflatoxin; aromatic ether; aromatic ketone	carcinogenic agent; human metabolite
4-bromo-2,3-dioxobutyl-coenzyme a [no description available]	2.65	3	0
glucosamine 1-phosphate [no description available]	2.05	1	0	glucosamine phosphate	Escherichia coli metabolite
carboxy phosphate carboxyphosphoric acid : An acyclic mixed acid anhydride formed by condensation of phosphoric acid with carbonic acid.	2.41	2	0	acyclic mixed acid anhydride; one-carbon compound; organic phosphate
erythritol [no description available]	2	1	0	butane-1,2,3,4-tetrol	antioxidant; human metabolite; plant metabolite
deoxycholic acid Deoxycholic Acid: A bile acid formed by bacterial action from cholate. It is usually conjugated with glycine or taurine. Deoxycholic acid acts as a detergent to solubilize fats for intestinal absorption, is reabsorbed itself, and is used as a choleretic and detergent.. deoxycholic acid : A bile acid that is 5beta-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 12 respectively.	2.36	2	0	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human blood serum metabolite
lanosterol [no description available]	1.95	1	0	14alpha-methyl steroid; 3beta-sterol; tetracyclic triterpenoid	bacterial metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
anisomycin Anisomycin: An antibiotic isolated from various Streptomyces species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system.. (-)-anisomycin : An antibiotic isolated from various Streptomyces species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system.	2.31	1	0	monohydroxypyrrolidine; organonitrogen heterocyclic antibiotic	anticoronaviral agent; antimicrobial agent; antineoplastic agent; antiparasitic agent; bacterial metabolite; DNA synthesis inhibitor; protein synthesis inhibitor
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	2.82	3	0
withaferin a withaferin A: an antiestrogen and phytogenic antineoplastic agent isolated from leaves of Withania somnifera Dun.; structure. withaferin A : A withanolide that is 5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione substituted by hydroxy groups at positions 4 and 27 (the 4beta,5beta,6beta,22R stereoisomer). Isolated from Physalis longifolia, it exhibits cytotoxic activity.	2.15	1	0	27-hydroxy steroid; 4-hydroxy steroid; delta-lactone; enone; epoxy steroid; ergostanoid; primary alcohol; secondary alcohol; withanolide	antineoplastic agent; apoptosis inducer
withanolides Withanolides: Ergostane derivatives of 28 carbons with oxygens at C1, C22, and C26 positions and the side chain cyclized. They are found in WITHANIA plant genus and have cytotoxic and other effects.	2.15	1	0
rosiglitazone 7,8-diacetoxy-4-methylcoumarin: possess strong antioxidant and radical scavenging activities; structure in first source. 7,8-diacetoxy-4-methylcoumarin : A coumarin substituted by a methyl group at position 4 and by acetyloxy groups at positions 7 and 8. It exhibits strong antioxidant and radical scavenging properties.	2.01	1	0	acetate ester; coumarins; diester	pro-angiogenic agent; radical scavenger
s-adenosylhomocysteine S-Adenosylhomocysteine: 5'-S-(3-Amino-3-carboxypropyl)-5'-thioadenosine. Formed from S-adenosylmethionine after transmethylation reactions.. S-adenosyl-L-homocysteine : An organic sulfide that is the S-adenosyl derivative of L-homocysteine.	2.41	2	0	adenosines; amino acid zwitterion; homocysteine derivative; homocysteines; organic sulfide	cofactor; EC 2.1.1.72 [site-specific DNA-methyltransferase (adenine-specific)] inhibitor; EC 2.1.1.79 (cyclopropane-fatty-acyl-phospholipid synthase) inhibitor; epitope; fundamental metabolite
glyceraldehyde 3-phosphate Glyceraldehyde 3-Phosphate: An aldotriose which is an important intermediate in glycolysis and in tryptophan biosynthesis.. glyceraldehyde 3-phosphate : An aldotriose phosphate that is the 3-phospho derivative of glyceraldehyde. It is an important metabolic intermediate in several central metabolic pathways in all organisms.	2.69	3	0	glyceraldehyde 3-phosphate	mouse metabolite
5'-methylthioadenosine 5'-methylthioadenosine: structure. 5'-S-methyl-5'-thioadenosine : Adenosine with the hydroxy group at C-5' substituted with a methylthio (methylsulfanyl) group.	2.02	1	0	thioadenosine	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
glycogen glycogen : A polydisperse, highly branched glucan composed of chains of D-glucopyranose residues in alpha(1->4) glycosidic linkage, joined together by alpha(1->6) glycosidic linkages. A small number of alpha(1->3) glycosidic linkages and some cumulative alpha(1->6) links also may occur. The branches in glycogen typically contain 8 to 12 glucose residues.	9.91	38	4
ribulose 5-phosphate ribulose 5-phosphate: RN given refers to cpd without isomeric designation. D-ribulose 5-phosphate : The D-enantiomer of ribulose 5-phosphate that is one of the end-products of the pentose phosphate pathway.. ribulose 5-phosphate : A ribulose phosphate in which the phosphate group is attached at position 5.	2.05	1	0	ribulose 5-phosphate	mouse metabolite
arabinose [no description available]	2.01	1	0	L-arabinose	Escherichia coli metabolite; mouse metabolite
n-acetylneuraminic acid N-Acetylneuraminic Acid: An N-acyl derivative of neuraminic acid. N-acetylneuraminic acid occurs in many polysaccharides, glycoproteins, and glycolipids in animals and bacteria. (From Dorland, 28th ed, p1518). N-acetylneuraminic acid : An N-acylneuraminic acid where the N-acyl group is specified as acetyl.	3.11	5	0	N-acetylneuraminic acids	antioxidant; bacterial metabolite; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor; human metabolite; mouse metabolite
glucosamine D-glucosamine : An amino sugar whose structure comprises D-glucose having an amino substituent at position 2.. 2-amino-2-deoxy-D-glucopyranose : A D-glucosamine whose structure comprises D-glucopyranose having an amino substituent at position 2.	3.72	10	0	D-glucosamine	Escherichia coli metabolite; geroprotector; mouse metabolite
glucosamine 6-phosphate glucosamine 6-phosphate: RN given refers to parent cpd	2.97	4	0	2-amino-2-deoxy-D-glucopyranose 6-phosphate	human metabolite; Saccharomyces cerevisiae metabolite
carnosine polaprezinc: stimulates bone growth	2.17	1	0	amino acid zwitterion; dipeptide	anticonvulsant; antineoplastic agent; antioxidant; Daphnia magna metabolite; geroprotector; human metabolite; mouse metabolite; neuroprotective agent
mevalonic acid Mevalonic Acid: A dihydroxy monocarboxylic acid and precursor in the biosynthetic pathway known as the mevalonate pathway, which produces terpenes and steroids that are vital for diverse cellular functions.. mevalonic acid : A racemate composed of equimolar amounts of (R)- and (S)-mevalonic acid.. (R)-mevalonic acid : The (R)-enantiomer of mevalonic acid.	8.17	63	0	3,5-dihydroxy-3-methylpentanoic acid
naringenin (S)-naringenin : The (S)-enantiomer of naringenin.	2	1	0	(2S)-flavan-4-one; naringenin	expectorant; plant metabolite
diaminopimelic acid Diaminopimelic Acid: A diamino derivative of heptanedioic acid with amino groups at C-2 and C-6 and the general formula (COOH)CH(NH2)CH2CH2CH2CH(NH2)(COOH).. LL-2,6-diaminopimelic acid : A 2,6-diaminopimelic acid in which both chiral centres have S configuration. It is a component of bacterial cell wall.	2	1	0	2,6-diaminopimelic acid; amino acid zwitterion	Escherichia coli 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.	3.76	11	0	pantetheines; thiol	human metabolite; metabolite; mouse metabolite
dithioerythritol [no description available]	1.98	1	0	1,4-dimercaptobutane-2,3-diol	reducing agent
puromycin [no description available]	2.71	3	0	puromycins	antiinfective agent; antimicrobial agent; antineoplastic agent; EC 3.4.11.14 (cytosol alanyl aminopeptidase) inhibitor; EC 3.4.14.2 (dipeptidyl-peptidase II) inhibitor; nucleoside antibiotic; protein synthesis inhibitor
hemoglobin randwick hemoglobin Randwick: unstable beta chain hemoglobin variant; Try replaced by Gly on beta chain 15(A12). (1->4)-beta-D-mannan : A mannan composed from D-mannan residues joined by beta-(1->4) linkages.. beta-D-mannose : A D-mannopyranose in which the anomeric centre has beta-configuration.. (1->2)-beta-D-mannan : A mannan consisting of repeating mannosyl units joined via beta-(1->2)-linkages.	1.98	1	0	D-mannopyranose	epitope
trimethyllysine trimethyllysine: stimulates growth of tumor cells; RN given refers to (S)-isomer	1.97	1	0	alpha-amino-acid cation	human metabolite; mouse metabolite
n-acetylglucosamine-1-phosphate N-acetylglucosamine-1-phosphate: found in proteinase I from Dictyostelium discoideum. N-acetyl-D-glucosamine 1-phosphate : A N-acyl-D-glucosamine 1-phosphate in which the acyl group specified is acetyl.. 2-acetamido-2-deoxy-D-glucopyranose 1-phosphate : A N-acetyl-D-glucosamine 1-phosphate that is 2-deoxy-D-glucopyranose 1-(dihydrogen phosphate) substituted by an acetamido group at position 2.	2.48	2	0	N-acetyl-D-glucosamine 1-phosphate	Escherichia coli metabolite; human metabolite; mouse metabolite
acetyl adenylate acetyl adenylate: used to acetylate histones in chromatin	2.1	1	0	5'-acylphosphoadenosin	human metabolite; mouse metabolite
thienamycin thienamycin: beta-lactam antibiotic; RN given refers to cpd without isomeric designation	2.02	1	0	carbapenems
sq 27860 carbapenem-3-carboxylic acid: from species of Serratia & Erwinia; carbapenam antibiotic; structure given in first source. 1-carbapenem-3-carboxylic acid : A carbapenemcarboxylic acid that is the 3-carboxy derivative of 2,3-didehydro-1-carbapenam.	2.02	1	0	alpha,beta-unsaturated monocarboxylic acid; carbapenemcarboxylic acid
actinorhodin actinorhodin: structure. actinorhodin : A member of the class of benzoisochromanequinone that is produced by Streptomyces coelicolor A3(2) and exhibits antibiotic activity.	1.98	1	0
mycothiol mycothiol: a glyco-inositol-cysteine found in MYCOBACTERIUM BOVIS which conjugates exogenous compounds for detoxication; it is a microbe counterpart to eucaryotic GLUTATHIONE; acted on by mycothiol disulfide reductase and mycothiol S-conjugate amidase and MDF dehydrogenase;. mycothiol S-conjugate : Any S-conjugate of mycothiol.. mycothiol : A pseudodisaccharide, 1D-myo-inosityl-alpha-D-glucopyranoside, in which the hydroxy group at the 2-position of the glucose moiety is replaced by an (N-acetyl-L-cysteinyl)amido group.	2.02	1	0
cefoxitin Cefoxitin: A semisynthetic cephamycin antibiotic resistant to beta-lactamase.. cefoxitin : A semisynthetic cephamycin antibiotic which, in addition to the methoxy group at the 7alpha position, has 2-thienylacetamido and carbamoyloxymethyl side-groups. It is resistant to beta-lactamase.	2.08	1	0	beta-lactam antibiotic allergen; cephalosporin; cephamycin; semisynthetic derivative	antibacterial drug
plasminogen activator inhibitor 2 N-butyrylhomoserine lactone: quorum sensing compound biosynthesized by LasI protein; structure given in first source	1.99	1	0	N-acyl-amino acid
sodium arsenite sodium arsenite : An inoganic sodium salt with formula with formula NaAsO2.	2.77	3	0	arsenic molecular entity; inorganic sodium salt	antibacterial agent; antifungal agent; antineoplastic agent; carcinogenic agent; herbicide; insecticide; rodenticide
isoshinanolone isoshinanolone: from crude extracts; structure in first source	2.41	1	0	tetralins
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	2.02	1	0	cyclodextrin
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.	2.36	2	0	butenedioic acid	algal metabolite; mouse metabolite; plant metabolite
dephosphocoenzyme a 3'-dephospho-CoA : An adenosine 5'-phosphate that is coenzyme A in which the phosphate group at position 3' has been replaced by a hydrogen atom. It is an intermediate metabolite in pantothenate and CoA biosynthesis.	2.95	4	0	adenosine 5'-phosphate	Escherichia coli metabolite; human metabolite; mouse metabolite
ergosterol [no description available]	3.22	6	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; ergostanoid; phytosterols	fungal metabolite; Saccharomyces cerevisiae metabolite
trichostatin a trichostatin A: chelates zinc ion in the active site of histone deacetylases, resulting in preventing histone unpacking so DNA is less available for transcription; do not confuse with TRICHOSANTHIN which is a protein; found in STREPTOMYCES	2.44	2	0	antibiotic antifungal agent; hydroxamic acid; trichostatin	bacterial metabolite; EC 3.5.1.98 (histone deacetylase) inhibitor; geroprotector
tretinoin Tretinoin: An important regulator of GENE EXPRESSION during growth and development, and in NEOPLASMS. Tretinoin, also known as retinoic acid and derived from maternal VITAMIN A, is essential for normal GROWTH; and EMBRYONIC DEVELOPMENT. An excess of tretinoin can be teratogenic. It is used in the treatment of PSORIASIS; ACNE VULGARIS; and several other SKIN DISEASES. It has also been approved for use in promyelocytic leukemia (LEUKEMIA, PROMYELOCYTIC, ACUTE).. retinoic acid : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraenoic acid substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).. all-trans-retinoic acid : A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry.	4	4	0	retinoic acid; vitamin A	anti-inflammatory agent; antineoplastic agent; antioxidant; AP-1 antagonist; human metabolite; keratolytic drug; retinoic acid receptor agonist; retinoid X receptor agonist; signalling molecule
carboxymethyl-coenzyme a carboxymethyl-coenzyme A: structure given in first source. carboxymethyl-CoA : An S-alkyl-CoA having carboxymethyl as the S-alkyl component.	2.67	3	0	S-alkyl-CoA	Brassica napus metabolite; EC 2.3.3.1 [citrate (Si)-synthase] inhibitor
arachidonic acid icosa-5,8,11,14-tetraenoic acid : Any icosatetraenoic acid with the double bonds at positions 5, 8, 11 and 14.. arachidonate : A long-chain fatty acid anion resulting from the removal of a proton from the carboxy group of arachidonic acid.	2.71	3	0	icosa-5,8,11,14-tetraenoic acid; long-chain fatty acid; omega-6 fatty acid	Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite; mouse metabolite
alpha-cyclodextrin alpha-cyclodextrin : A cycloamylose composed of six alpha-(1->4) linked D-glucopyranose units.	2.02	1	0	cyclodextrin
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.	2.42	2	0	butenedioic acid	food acidity regulator; fundamental metabolite; geroprotector
farnesol Farnesol: A colorless liquid extracted from oils of plants such as citronella, neroli, cyclamen, and tuberose. It is an intermediate step in the biological synthesis of cholesterol from mevalonic acid in vertebrates. It has a delicate odor and is used in perfumery. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). (2-trans,6-trans)-farnesol : The (2-trans,6-trans)-stereoisomer of farnesol.. farnesol : A farnesane sesquiterpenoid that is dodeca-2,6,10-triene substituted by methyl groups at positions 3, 7 and 11 and a hydroxy group at position 1.	2.35	2	0	farnesol	plant metabolite
3-hydroxy-3-methylglutaryl-coenzyme a 3-hydroxy-3-methylglutaryl-coenzyme A: RN given refers to cpd without isomeric designation. 3-hydroxy-3-methylglutaryl-CoA : An alpha,omega dicarboxyacyl-CoA that results from the formal condensation of the thiol group of coenzyme A with one of the carboxy groups of 3-hydroxy-3-methylglutaric acid.. (3S)-3-hydroxy-3-methylglutaryl-CoA : A 3-hydroxy-3-methylglutaryl-CoA where the 3-hydroxy-3-methylglutaryl component has (S)-configuration.	6.55	20	0	3-hydroxy-3-methylglutaryl-CoA; 3-hydroxy fatty acyl-CoA	human metabolite; mouse metabolite
resveratrol trans-resveratrol : A resveratrol in which the double bond has E configuration.	4.43	4	0	resveratrol	antioxidant; phytoalexin; plant metabolite; quorum sensing inhibitor; radical scavenger
retinol Vitamin A: Retinol and derivatives of retinol that play an essential role in metabolic functioning of the retina, the growth of and differentiation of epithelial tissue, the growth of bone, reproduction, and the immune response. Dietary vitamin A is derived from a variety of CAROTENOIDS found in plants. It is enriched in the liver, egg yolks, and the fat component of dairy products.. vitamin A : Any member of a group of fat-soluble retinoids produced via metabolism of provitamin A carotenoids that exhibit biological activity against vitamin A deficiency. Vitamin A is involved in immune function, vision, reproduction, and cellular communication.. all-trans-retinol : A retinol in which all four exocyclic double bonds have E- (trans-) geometry.. retinol : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraen-1-ol substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).	3.64	2	0	retinol; vitamin A	human metabolite; mouse metabolite; plant metabolite
oleic acid Oleic Acid: An unsaturated fatty acid that is the most widely distributed and abundant fatty acid in nature. It is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. (Stedman, 26th ed). oleic acid : An octadec-9-enoic acid in which the double bond at C-9 has Z (cis) stereochemistry.	5.06	16	0	octadec-9-enoic acid	antioxidant; Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; Escherichia coli metabolite; mouse metabolite; plant metabolite; solvent
farnesyl pyrophosphate farnesyl pyrophosphate: a sesquiterpene that dimerizes to SQUALENE; RN given refers to cpd without isomeric designation. 2-trans,6-trans-farnesyl diphosphate : The trans,trans-stereoisomer of farnesyl diphosphate.	4.05	4	0	farnesyl diphosphate	Escherichia coli metabolite; mouse metabolite
ferulic acid ferulate : A monocarboxylic acid anion obtained by the deprotonation of the carboxy group of ferulic acid.	2.42	2	0	ferulic acids	anti-inflammatory agent; antioxidant; apoptosis inhibitor; cardioprotective agent; MALDI matrix material; plant metabolite
pectins Pectins: High molecular weight polysaccharides present in the cell walls of all plants. Pectins cement cell walls together. They are used as emulsifiers and stabilizers in the food industry. They have been tried for a variety of therapeutic uses including as antidiarrheals, where they are now generally considered ineffective, and in the treatment of hypercholesterolemia.. alpha-D-galacturonic acid : The alpha-anomer of D-galacturonic acid.	2.63	2	0	D-galactopyranuronic acid
1,5-dihydro-fad 1,5-dihydro-FAD: chromophore component of E coli DNA photolyase	3.31	1	0	flavin adenine dinucleotide	Escherichia coli metabolite; mouse metabolite
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.	2.91	4	0	icosapentaenoic acid; omega-3 fatty acid	anticholesteremic drug; antidepressant; antineoplastic agent; Daphnia galeata metabolite; fungal metabolite; micronutrient; mouse metabolite; nutraceutical
lycopene [no description available]	2.94	3	0	acyclic carotene	antioxidant; plant metabolite
geranylgeranyl pyrophosphate geranylgeranyl pyrophosphate: RN given refers to (E,E,E)-isomer. geranylgeranyl diphosphate : A polyprenol diphosphate having geranylgeranyl as the polyprenyl component.. 2-trans,6-trans,10-trans-geranylgeranyl diphosphate : The all-trans-isomer of geranylgeranyl diphosphate.	1.98	1	0	geranylgeranyl diphosphate	mouse metabolite
cytidine monophosphate n-acetylneuraminic acid Cytidine Monophosphate N-Acetylneuraminic Acid: A nucleoside monophosphate sugar which donates N-acetylneuraminic acid to the terminal sugar of a ganglioside or glycoprotein.. CMP-N-acetyl-beta-neuraminic acid : A nucleotide sugar used as a donor by glycosyltransferases for the synthesis of sugar chains	3.08	5	0	CMP-N-acyl-beta-neuraminic acid	mouse metabolite
pantethine pantethine: RN given refers to cpd without isomeric designation; structure. pantethine : An organic disulfide that consists of two molecules of pantothenic acid linked by amide bonds to a cysteamine disulfide bridging group.	2.4	2	0	organic disulfide	coenzyme; nutraceutical
dactinomycin Dactinomycin: A compound composed of a two CYCLIC PEPTIDES attached to a phenoxazine that is derived from STREPTOMYCES parvullus. It binds to DNA and inhibits RNA synthesis (transcription), with chain elongation more sensitive than initiation, termination, or release. As a result of impaired mRNA production, protein synthesis also declines after dactinomycin therapy. (From AMA Drug Evaluations Annual, 1993, p2015)	2.35	2	0	actinomycin	mutagen
streptothricins Streptothricins: A group of antibiotic aminoglycosides differing only in the number of repeating residues in the peptide side chain. They are produced by Streptomyces and Actinomyces and may have broad spectrum antimicrobial and some antiviral properties.. streptothricin : An N-glycosyl compound consisting of 2-amino-4-O-carbamoyl-2-deoxy-N-[(3aS,7R,7aS)-7-hydroxy-4-oxooctahydro-2H-imidazo[4,5-c]pyridin-2-ylidene]-beta-D-gulopyranosylamine in which the amino group at position 2 of the gulopyranosyl moiety is acylated by a peptide unit made up of between 1 and 7 N(epsilon)-linked units of beta-lysine.	1.99	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).	2.71	3	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.	1.97	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.	2.96	4	0	organic sodium salt	NMR chemical shift reference compound
sodium cyanate sodium cyanate: used in treatment of sickle cell anemia; RN given refers to cyanic acid, Na salt	2.07	1	0	cyanate salt; one-carbon compound
ammonium acetate ammonium acetate : An ammonium salt obtained by reaction of ammonia with acetic acid. A deliquescent white crystalline solid, it has a relatively low melting point (114degreeC) for a salt. Used as a food acidity regulator, although no longer approved for this purpose in the EU.	2.37	2	0	acetate salt; ammonium salt	buffer; food acidity regulator
methyl thioacetate [no description available]	2.4	2	0	thionoester
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.	2.17	1	0	2-butenoic acid	plant metabolite
geraniol [no description available]	2.13	1	0	3,7-dimethylocta-2,6-dien-1-ol; monoterpenoid; primary alcohol	allergen; fragrance; plant metabolite; volatile oil component
glycosides [no description available]	2.66	3	0
isomethyleugenol Methylation: Addition of methyl groups. In histo-chemistry methylation is used to esterify carboxyl groups and remove sulfate groups by treating tissue sections with hot methanol in the presence of hydrochloric acid. (From Stedman, 25th ed)	6.68	30	0	isomethyleugenol
beta-ionone beta-ionone: stimulator of carotenogenesis; carotenoid inhibitor; intermediate in synthesis of Vit A; RN given refers to cpd without isomeric designation; structure. beta-ionone : An ionone that is but-3-en-2-one substituted by a 2,6,6-trimethylcyclohex-1-en-1-yl group at position 4.	2.25	1	0	ionone	antioxidant; fragrance
squalene Addavax: an oil-water nanoemulsion and adjuvant containing squalene, Tween 80, and sorbitane trioleate	4.79	10	0	triterpene	human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	4.2	3	0	stilbene
averufin averufin: isolated from Aspergillus sp.; has antifungal activity	3.12	1	0	cyclic ketal; organic heteropentacyclic compound; polyketide; polyphenol	fungal metabolite
ricinoleic acid ricinoleic acid: RN given refers to (R-(Z))-isomer; structure in Merck Index, 9th ed, #8005. ricinoleic acid : A (9Z)-12-hydroxyoctadec-9-enoic acid in which the 12-hydroxy group has R-configuration..	2.03	1	0	(9Z)-12-hydroxyoctadec-9-enoic acid
citraconic acid citraconic acid: was MH 1975-92 (see under MALEATES 1975-90); METHYLMALEIC ACID was see CITRACONIC ACID 1975-92; use MALEATES to search CITRACONIC ACID 1975-92; RN refers to (Z)-isomer; SO refers to (E)-isomer. citraconic acid : A dicarboxylic acid consisting of maleic acid having a methyl substituent at the 2-position.	2.49	2	0	dicarboxylic acid; dicarboxylic fatty acid	human metabolite
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)	6.34	13	0	flavin adenine dinucleotide; vitamin B2	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; prosthetic group
3-hydroxybutyryl-coenzyme a 3-hydroxybutyryl-coenzyme A: RN given refers to cpd without isomeric designation. 3-hydroxybutanoyl-CoA : A hydroxybutanoyl-CoA having 3-hydroxybutanoyl as the S-acyl component.	3.1	5	0	3-hydroxyacyl-CoA; hydroxybutanoyl-CoA	mouse 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.	9.64	181	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.	9.65	8	0	diphosphate ion
palmitoyl coenzyme a Palmitoyl Coenzyme A: A fatty acid coenzyme derivative which plays a key role in fatty acid oxidation and biosynthesis.. palmitoyl-CoA : A long-chain fatty acyl-CoA resulting from the formal condensation of the carboxy group of hexadecanoic acid with the thiol group of coenzyme A.	4.23	18	0	11,12-saturated fatty acyl-CoA; 3-substituted propionyl-CoA; long-chain fatty acyl-CoA; palmitoyl bioconjugate	Escherichia coli metabolite; mouse metabolite
acetyl-aspartyl-glutamyl-valyl-aspartal acetyl-aspartyl-glutamyl-valyl-aspartal: a capase inhibitor. Ac-Asp-Glu-Val-Asp-H : A tetrapeptide consisting of two L-aspartic acid residues, an L-glutamyl residue and an L-valine residue with an acetyl group at the N-terminal and with the C-terminal carboxy group reduced to an aldehyde. It is an inhibitor of caspase-3/7.	2.02	1	0	tetrapeptide	protease inhibitor
isopropyl thiogalactoside Isopropyl Thiogalactoside: A non-metabolizable galactose analog that induces expression of the LAC OPERON.. isopropyl beta-D-thiogalactopyranoside : An S-glycosyl compound consisting of beta-D-1-thiogalactose having an isopropyl group attached to the anomeric sulfur.	3.06	4	0	S-glycosyl compound
sesquiterpenes [no description available]	5.25	15	0
3,3',4,5'-tetrahydroxystilbene 3,3',4,5'-tetrahydroxystilbene: demethyl derivative of isorhapontigenin; structure in first source; a Syk kinase inhibitor; found in heartwood of FABACEAE; inhibitor of photosynthesis in spinach chloroplasts; may be inhibitor of plant growth; RN given refers to (E)-isomer. piceatannol : A stilbenol that is trans-stilbene in which one of the phenyl groups is substituted by hydroxy groups at positions 3 and 4, while the other phenyl group is substituted by hydroxy groups at positions 3 and 5.	2.17	1	0	catechols; polyphenol; resorcinols; stilbenol	antineoplastic agent; apoptosis inducer; geroprotector; hypoglycemic agent; plant metabolite; protein kinase inhibitor; tyrosine kinase inhibitor
caffeic acid trans-caffeic acid : The trans-isomer of caffeic acid.	2.03	1	0	caffeic acid	geroprotector; mouse metabolite
curcumin Curcumin: A yellow-orange dye obtained from tumeric, the powdered root of CURCUMA longa. It is used in the preparation of curcuma paper and the detection of boron. Curcumin appears to possess a spectrum of pharmacological properties, due primarily to its inhibitory effects on metabolic enzymes.. curcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa.	4.43	4	0	aromatic ether; beta-diketone; diarylheptanoid; enone; polyphenol	anti-inflammatory agent; antifungal agent; antineoplastic agent; biological pigment; contraceptive drug; dye; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; EC 1.8.1.9 (thioredoxin reductase) inhibitor; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; flavouring agent; food colouring; geroprotector; hepatoprotective agent; immunomodulator; iron chelator; ligand; lipoxygenase inhibitor; metabolite; neuroprotective agent; nutraceutical; radical scavenger
rhodanine 2-mercaptothiazolinone: metabolite in urine from persons exposed to CS2; structure	2.03	1	0	thiazolidinone
methimazole Methimazole: A thioureylene antithyroid agent that inhibits the formation of thyroid hormones by interfering with the incorporation of iodine into tyrosyl residues of thyroglobulin. This is done by interfering with the oxidation of iodide ion and iodotyrosyl groups through inhibition of the peroxidase enzyme.. methimazole : A member of the class of imidazoles that it imidazole-2-thione in which a methyl group replaces the hydrogen which is attached to a nitrogen.	1.96	1	0	1,3-dihydroimidazole-2-thiones	antithyroid drug
3-methylglutaconic acid (E)-3-methylglutaconic acid : A dicarboxylic acid comprising (E)-glutaconic acid carrying a 3-methyl substituent.	4.37	3	0	dicarboxylic acid
chlorogenic acid caffeoylquinic acid: Antiviral Agent; structure in first source. chlorogenate : A monocarboxylic acid anion that is the conjugate base of chlorogenic acid; major species at pH 7.3.	2.41	1	0	cinnamate ester; tannin	food component; plant metabolite
sodium propionate sodium propionate: was term of propionic acid (1986-2006). sodium propionate : An organic sodium salt comprising equal numbers of sodium and propionate ions.	2.25	1	0	organic sodium salt	antifungal drug; food preservative
D-fructopyranose [no description available]	5.26	20	0	cyclic hemiketal; D-fructose; fructopyranose	sweetening agent
thioacetamide Thioacetamide: A crystalline compound used as a laboratory reagent in place of HYDROGEN SULFIDE. It is a potent hepatocarcinogen.. thioacetamide : A thiocarboxamide consiting of acetamide having the oxygen replaced by sulfur.	2.25	1	0	thiocarboxamide	hepatotoxic agent
unithiol Unithiol: A chelating agent used as an antidote to heavy metal poisoning.	2.45	2	0
succimer Succimer: A mercaptodicarboxylic acid used as an antidote to heavy metal poisoning because it forms strong chelates with them.. succimer : A sulfur-containing carboxylic acid that is succinic acid bearing two mercapto substituents at positions 2 and 3. A lead chelator used as an antedote to lead poisoning.	2.45	2	0	dicarboxylic acid; dithiol; sulfur-containing carboxylic acid	chelator
fumonisin b2 fumonisin B2: produced by Fusarium moniliforme MRC 826; structure given in first source; has cancer-promoting ability. fumonisin B2 : A fumonisin that is (2S,3S,12S,14S,15R,16R)-2-amino-12,16-dimethylicosane-3,14,15-triol in which the hydroxy groups at positions 14 and 15 have each been esterified by condensation with the 1-carboxy group of 3-carboxyglutaric acid (giving a 3-carboxyglutarate ester group with R configuration in each case).	2.05	1	0	diester; diol; fumonisin; primary amino compound	Aspergillus metabolite; carcinogenic agent
nadp [no description available]	10.43	122	0
8-azidoadenosine 5'-triphosphate [no description available]	1.98	1	0
5-carboxytetramethylrhodamine succinimidyl ester [no description available]	2.31	1	0
camphorquinone-10-sulfonic acid camphorquinone-10-sulfonic acid: structure given in first source	1.96	1	0
oxalomalic acid oxalomalic acid: structure	2.04	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.	2.65	3	0	alkali metal atom
cobaltous chloride cobaltous chloride: RN given refers to unlabeled cpd; RN in Chemline for cobalt trichloride: 10241-04-0; RN for 60-labeled cpd: 14543-09-0; RN for 57-labeled cpd: 164113-89-1; RN for 58-labeled cpd: 29377-09-1; structure. cobalt dichloride : A cobalt salt in which the cobalt metal is in the +2 oxidation state and the counter-anion is chloride. It is used as an indicator for water in desiccants.	2.08	1	0	cobalt salt; inorganic chloride	allergen; calcium channel blocker; sensitiser; two-colour indicator
1,2-bis(2-aminophenoxy)ethane n,n,n',n'-tetraacetic acid acetoxymethyl ester [no description available]	2.1	1	0
mdl 72527 MDL 72527: RN given refers to di-HCl; RN for parent cpd not available 6/85; polyamine oxidase inhibitor	2.02	1	0
cystine [no description available]	2.41	1	0
isobutyryl-coenzyme a [no description available]	2.01	1	0	methyl-branched fatty acyl-CoA; short-chain fatty acyl-CoA	human metabolite; mouse metabolite
safingol safingol: RN given refers to the (R-(R,S))-isomer	1.99	1	0	amino alcohol
glutaryl-coenzyme a [no description available]	2.66	3	0	glutaryl-CoAs	mouse metabolite
chloroacetyl coenzyme a [no description available]	3.22	6	0
nafenopin-coenzyme a nafenopin-coenzyme A: rat liver microsomal thioester metabolite	1.98	1	0
lactoyl-coenzyme a lactoyl-coenzyme A: used by Clostridium propionicum in the conversion of lactate to propionate	2.21	1	0	hydroxyacyl-CoA
citryl-coenzyme a [no description available]	2.66	3	0
succinyl phosphate succinyl phosphate: RN given refers to parent cpd	2.41	1	0
pimeloyl-coenzyme a pimeloyl-CoA : An omega carboxyacyl-CoA that is the S-pimeloyl derivative of coenzyme A.	2.43	2	0	omega-carboxyacyl-CoA	metabolite
acetyldithio-coenzyme a acetyldithio-coenzyme A: RN given in first source	2.02	1	0
allatostatin 1 allatostatin 1: inhibits juvenile hormone synthesis; from reproductively active females	1.99	1	0
phosphothreonine Phosphothreonine: The phosphoric acid ester of threonine. Used as an identifier in the analysis of peptides, proteins, and enzymes.. O-phospho-L-threonine : A L-threonine derivative phosphorylated at the side-chain hydroxy function.	1.99	1	0	L-threonine derivative; non-proteinogenic L-alpha-amino acid; O-phosphoamino acid	Escherichia coli metabolite
ovalbumin Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.	2.87	4	0
sodium dodecyl sulfate Sodium Dodecyl Sulfate: An anionic surfactant, usually a mixture of sodium alkyl sulfates, mainly the lauryl; lowers surface tension of aqueous solutions; used as fat emulsifier, wetting agent, detergent in cosmetics, pharmaceuticals and toothpastes; also as research tool in protein biochemistry.. sodium dodecyl sulfate : An organic sodium salt that is the sodium salt of dodecyl hydrogen sulfate.	3.21	6	0	organic sodium salt	detergent; protein denaturant
2,4-dinitrophenylhydrazine 2,4-dinitrophenylhydrazine: structure. 2,4-dinitrophenylhydrazine : A C-nitro compound that is phenylhydrazine substituted at the 2- and 4-positions by nitro groups.	1.98	1	0	C-nitro compound; phenylhydrazines	reagent
homoserine lactone homoserine lactone: a putative signal for starvation in E. coli; structure in first source. homoserinium lactone : The conjugate acid of homoserine lactone; major species at pH 7.3.. homoserine lactone : A butan-4-olide having an amino substituent at the 2-position.	1.99	1	0	ammonium ion derivative; organic cation
alpha-chymotrypsin Chymotrypsin: A serine endopeptidase secreted by the pancreas as its zymogen, CHYMOTRYPSINOGEN and carried in the pancreatic juice to the duodenum where it is activated by TRYPSIN. It selectively cleaves aromatic amino acids on the carboxyl side.	3.75	3	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.	2.41	1	0
citramalate citramalate: RN given refers to cpd without isomeric designation. citramalate(2-) : A dicarboxylic acid dianion that is obtained by removal of a proton from both of the carboxylic acid groups of citramalic acid.	3.51	8	0	dicarboxylic acid dianion	human metabolite; plant metabolite
2-mercaptoacetate 2-mercaptoacetate: RN given refers to parent cpd	2.36	2	0	monocarboxylic acid anion
sphingosine sphing-4-enine : A sphingenine in which the C=C double bond is located at the 4-position.. sphingenine : A 2-aminooctadecene-1,3-diol having (2S,3R)-configuration.. sphingoid : Sphinganine, its homologs and stereoisomers, and the hydroxy and unsaturated derivatives of these compounds.. 2-aminooctadec-4-ene-1,3-diol : A 2-aminooctadecene-1,3-diol having its double bond at position 4.	2.92	4	0	sphing-4-enine	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.	2.21	1	0	prostaglandins E	human metabolite; mouse metabolite; oxytocic
sterigmatocystin [no description available]	3.52	2	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.	3.03	4	0	carotenoid beta-end derivative; cyclic carotene	antioxidant; biological pigment; cofactor; ferroptosis inhibitor; human metabolite; mouse metabolite; plant metabolite; provitamin A
8,11,14-eicosatrienoic acid 8,11,14-Eicosatrienoic Acid: A 20-carbon-chain fatty acid, unsaturated at positions 8, 11, and 14. It differs from arachidonic acid, 5,8,11,14-eicosatetraenoic acid, only at position 5.. all-cis-icosa-8,11,14-trienoic acid : An icosatrienoic acid having three cis double bonds at positions 8, 11 and 14.	2.01	1	0	fatty acid 20:3; long-chain fatty acid	fungal metabolite; human metabolite; nutraceutical
(all-e) phytoene (all-E) phytoene: C40 carotenoid biosynthesized in bacteria; minor descriptor (75-84); EP to CAROTENOIDS (85); on-line & Index Medicus search CAROTENOIDS (75-85); RN given refers to (all-trans)-isomer; RN for cpd without isomeric designation. all-trans-phytoene : The all-trans-isomer of phytoene.	3.07	1	0	phytoene	plant metabolite
rutin Hydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders.	1.95	1	0	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite
lipoxin a4 lipoxin A4: an antifibrolytic agent; structure given in first source; a role in ASPIRIN antiinflammatory activity. lipoxin A4 : A C20 hydroxy fatty acid having (5S)-, (6R)- and (15S)-hydroxy groups as well as (7E)- (9E)-, (11Z)- and (13E)-double bonds.	2.17	1	0	hydroxy polyunsaturated fatty acid; lipoxin; long-chain fatty acid	human metabolite; metabolite
gamma-linolenic acid gamma-Linolenic Acid: An omega-6 fatty acid produced in the body as the delta 6-desaturase metabolite of linoleic acid. It is converted to dihomo-gamma-linolenic acid, a biosynthetic precursor of monoenoic prostaglandins such as PGE1. (From Merck Index, 11th ed). gamma-linolenic acid : A C18, omega-6 acid fatty acid comprising a linolenic acid having cis- double bonds at positions 6, 9 and 12.	2.77	3	0	linolenic acid; omega-6 fatty acid	human metabolite; mouse metabolite; plant metabolite
alpha-linolenic acid linolenic acid : A two-membered subclass of octadecatrienoic acid comprising the (9Z,12Z,15Z)- and (6Z,9Z,12Z)-isomers. Linolenic acids are nutrients essential to the formation of prostaglandins and are also used in making paints and synthetic resins.. linolenate : A polyunsaturated fatty acid anion obtained by deprotonation of the carboxy group of either alpha- or gamma-linolenic acid.	2.02	1	0	linolenic acid; omega-3 fatty acid	micronutrient; mouse metabolite; nutraceutical
clavulanic acid Clavulanic Acid: A beta-lactam antibiotic produced by the actinobacterium Streptomyces clavuligerus. It is a suicide inhibitor of bacterial beta-lactamase enzymes. Administered alone, it has only weak antibacterial activity against most organisms, but given in combination with other beta-lactam antibiotics it prevents antibiotic inactivation by microbial lactamase.. clavulanate : The conjugate base of clavulanic acid.. clavulanic acid : Antibiotic isolated from Streptomyces clavuligerus. It acts as a suicide inhibitor of bacterial beta-lactamase enzymes.	2.47	2	0	oxapenam	antibacterial drug; anxiolytic drug; bacterial metabolite; EC 3.5.2.6 (beta-lactamase) inhibitor
jasmonic acid jasmonic acid: a derivative of alpha-linolenic acid that has a role in plant response to herbivory analogous to the role of prostanoids in inflammation in mammals;. jasmonic acid : An oxo monocarboxylic acid that is (3-oxocyclopentyl)acetic acid substituted by a (2Z)-pent-2-en-1-yl group at position 2 of the cyclopentane ring.	2.03	1	0	oxo monocarboxylic acid	jasmonates; plant metabolite
astaxanthine astaxanthine: a keto form of carotene; pigment in flesh of Scottish salmon (Salmo salar) crustacoa-lobster (Homarus gammarus, flamingo feathers; structure; a carotenoid without vitamin A activity, has shown anti-oxidant and anti-inflammatory activities. astaxanthin : A carotenone that consists of beta,beta-carotene-4,4'-dione bearing two hydroxy substituents at positions 3 and 3' (the 3S,3'S diastereomer). A carotenoid pigment found mainly in animals (crustaceans, echinoderms) but also occurring in plants. It can occur free (as a red pigment), as an ester, or as a blue, brown or green chromoprotein.	2.11	1	0	carotenol; carotenone	animal metabolite; anticoagulant; antioxidant; food colouring; plant metabolite
alpha-farnesene alpha-farnesene: structure given in first source. alpha-farnesene : A farnesene that is 1,3,6,10-tetraene substituted by methyl groups at positions 3, 7 and 11 respectively.. farnesene : A sesquiterpene that is any of the four possible isomers of 3,7,11-trimethyl-1,3,6,10-dodecatetraene (alpha-farnesene) or of the two possible isomers of 7,11-dimethyl-3-methylene-1,6,10-dodecatriene.	2.25	1	0	alpha-farnesene
garcinol garcinol: from stem bark of Garcinia huillensis; has chemotherapeutic activity against gram-positive & gram-negative cocci, mycobacteria & fungi	3.89	2	0
chicoric acid chicoric acid: inhibits HIV-1 integrase	2.17	1	0	organooxygen compound	geroprotector; HIV-1 integrase inhibitor
caffeic acid phenethyl ester phenethyl caffeate : An alkyl caffeate ester in which 2-phenylethyl is the alkyl component.	2.15	1	0	alkyl caffeate ester	anti-inflammatory agent; antibacterial agent; antineoplastic agent; antioxidant; antiviral agent; immunomodulator; metabolite; neuroprotective agent
ellagic acid [no description available]	1.99	1	0	catechols; cyclic ketone; lactone; organic heterotetracyclic compound; polyphenol	antioxidant; EC 1.14.18.1 (tyrosinase) inhibitor; EC 2.3.1.5 (arylamine N-acetyltransferase) inhibitor; EC 2.4.1.1 (glycogen phosphorylase) inhibitor; EC 2.5.1.18 (glutathione transferase) inhibitor; EC 2.7.1.127 (inositol-trisphosphate 3-kinase) inhibitor; EC 2.7.1.151 (inositol-polyphosphate multikinase) inhibitor; EC 2.7.4.6 (nucleoside-diphosphate kinase) inhibitor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; EC 5.99.1.2 (DNA topoisomerase) inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; food additive; fungal metabolite; geroprotector; plant metabolite; skin lightening agent
soraphen a [no description available]	3.57	2	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.	1.99	1	0	ubiquinones	antioxidant; ferroptosis inhibitor; human metabolite
curacin a curacin A: RN refers to curacin A (the Z,E,E-isomer), the major lipid component of a strain of the marine cyanobacterium Lyngbya majuscula; structure given in first source	2.47	2	0	thiazoles
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.	3.68	10	0	epoxide; monocarboxylic acid amide	antifungal agent; antiinfective agent; antilipemic drug; antimetabolite; antimicrobial agent; fatty acid synthesis inhibitor
turimycin turimycin: macrolide antibiotic from Streptomyces hygroscopicus JA 6599; structure. leucomycin V : A macrolide antibiotic produced by Streptomyces kitasatoensis, showing activity against a wide spectrum of pathogens.	1.95	1	0	leucomycin; macrolide antibiotic	bacterial metabolite
menaquinone 6 menaquinone 6: RN given refers to (all-E)-isomer	2.11	1	0
sirolimus Sirolimus: A macrolide compound obtained from Streptomyces hygroscopicus that acts by selectively blocking the transcriptional activation of cytokines thereby inhibiting cytokine production. It is bioactive only when bound to IMMUNOPHILINS. Sirolimus is a potent immunosuppressant and possesses both antifungal and antineoplastic properties.. sirolimus : A macrolide lactam isolated from Streptomyces hygroscopicus consisting of a 29-membered ring containing 4 trans double bonds, three of which are conjugated. It is an antibiotic, immunosupressive and antineoplastic agent.	2.42	2	0	antibiotic antifungal drug; cyclic acetal; cyclic ketone; ether; macrolide lactam; organic heterotricyclic compound; secondary alcohol	antibacterial drug; anticoronaviral agent; antineoplastic agent; bacterial metabolite; geroprotector; immunosuppressive agent; mTOR inhibitor
menaquinone 7 menaquinone-7 : A menaquinone whose side-chain contains seven isoprene units in an all-trans-configutation.	2.11	1	0	menaquinone	bone density conservation agent; cofactor; Escherichia coli metabolite; human blood serum metabolite; Mycoplasma genitalium metabolite
anhydrovitamin a anhydrovitamin A: RN given refers to (all-E)-isomer; structure given in first source	3.17	1	0	sesquiterpenoid
xylulose [no description available]	1.99	1	0	xylulose	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
lysophosphatidic acid lysophosphatidic acid: RN given refers to parent cpd. 1-oleoyl-sn-glycerol 3-phosphate : A 1-acyl-sn-glycerol 3-phosphate having oleoyl as the 1-O-acyl group.. lysophosphatidic acid : A member of the class of lysophosphatidic acids obtained by hydrolytic removal of one of the two acyl groups of any phosphatidic acid. A 'closed' class.	2.03	1	0	1-acyl-sn-glycerol 3-phosphate
lysophosphatidylcholines lysophosphatidylcholine : An acylglycerophosphocholine resulting from partial hydrolysis of a phosphatidylcholine, which removes one of the fatty acyl groups. The structure is depicted in the image where R1 = acyl, R2 = H or where R1 = H, R2 = acyl.	3.35	7	0	1-O-acyl-sn-glycero-3-phosphocholine
beta-farnesene beta-farnesene: structure given in first source	2.54	2	0	beta-farnesene
caryophyllene caryophyllene: RN given refers to cpd without isomeric designation; structure given in first source	2.13	1	0
malealdehyde malealdehyde: RN given refers to cpd without isomeric designation; fumaraldehyde refers to (E)-isomer	1.96	1	0	but-2-enedial
casein kinase ii Casein Kinase II: A ubiquitous casein kinase that is comprised of two distinct catalytic subunits and dimeric regulatory subunit. Casein kinase II has been shown to phosphorylate a large number of substrates, many of which are proteins involved in the regulation of gene expression.	2.41	1	0
lead Lead: A soft, grayish metal with poisonous salts; atomic number 82, atomic weight 207.2, symbol Pb.	2.66	3	0	carbon group element atom; elemental lead; metal atom	neurotoxin
antimony Antimony: A metallic element that has the atomic symbol Sb, atomic number 51, and atomic weight 121.75. It is used as a metal alloy and as medicinal and poisonous salts. It is toxic and an irritant to the skin and the mucous membranes.	1.96	1	0	metalloid atom; pnictogen
aluminum Aluminum: A metallic element that has the atomic number 13, atomic symbol Al, and atomic weight 26.98.	5.73	11	0	boron group element atom; elemental aluminium; metal atom
arsenic Arsenic: A shiny gray element with atomic symbol As, atomic number 33, and atomic weight 75. It occurs throughout the universe, mostly in the form of metallic arsenides. Most forms are toxic. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), arsenic and certain arsenic compounds have been listed as known carcinogens. (From Merck Index, 11th ed)	3.35	7	0	metalloid atom; pnictogen	micronutrient
cefuroxime [no description available]	2.08	1	0
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.	3.68	9	0	chalcogen; nonmetal atom	macronutrient
4-phenyl-3-butenoic acid 4-phenyl-3-butenoic acid: an inhibitor of peptidyl glycine hydroxylase (peptide amidating enzyme); RN given refers to cpd without isomeric designation	3.1	1	0
plastoquinone [no description available]	1.99	1	0	plastoquinone
pederin pederin: isolated from beetles, Paederus fuscipes; minor descriptor (75-84); on-line & Index Medicus search PYRANS (75-84); RN given refers to (2S-(2alpha(R(R(2S,5S,6S))),4beta,6beta(R)))-isomer. pederin : A polyketide and carboxamide produced by a (Pseudomonas) bacterial endosymbiont of certain rove beetles (genus Paederus). Pederin is the agent responsible for the vesicant effects (linear or Paederus dermatitis) when the beetle is crushed against the skin. It is a powerful inhibitor of protein biosynthesis and mitosis and a potent antitumour agent.	2.5	2	0	cyclic ketal; diol; oxanes; polyketide; secondary alcohol; secondary carboxamide	antimitotic; antineoplastic agent; bacterial metabolite; vesicant
3-acetyldeoxynivalenol 3-acetyldeoxynivalenol : A trichothecene mycotoxin that is deoxynivalenol acetylated on the oxygen at C-3. A skin and eye irritant, along with its 15-acetyl regioisomer and its parent deoxynivalenol it is considered among the most commonly and widely distributed cereal contaminants.	2.08	1	0	trichothecene	epitope; mycotoxin
streptogramin a Streptogramin A: A specific streptogramin group A antibiotic produced by Streptomyces graminofaciens and other bacteria.	2.1	1	0	1,3-oxazoles; cyclic ketone; enamide; lactam; macrolide antibiotic; macrolide; pyrroline; secondary alcohol; secondary carboxamide; tertiary carboxamide	antibacterial drug; Mycoplasma genitalium metabolite
dimyristoylphosphatidylcholine 1,2-di-O-myristoyl-sn-glycero-3-phosphocholine : A 1,2-diacyl-sn-glycero-3-phosphocholine where the two phosphatidyl acyl groups are specified as tetradecanoyl (myristoyl).. dimyristoyl phosphatidylcholine : A phosphatidylcholine where the phosphatidyl acyl groups are specified as tetradecanoyl (myristoyl).	2.48	2	0	1,2-diacyl-sn-glycero-3-phosphocholine; phosphatidylcholine 28:0; tetradecanoate ester	antigen; mouse metabolite
fumarates Fumarates: Compounds based on fumaric acid.. fumarate(2-) : A C4-dicarboxylate that is the E-isomer of but-2-enedioate(2-)	5.23	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.	11.25	46	0	cysteinium	fundamental metabolite
isophthalate isophthalate: RN given refers to parent cpd	2.41	1	0	dicarboxylic acid dianion
7-mercaptoheptanoylthreonine phosphate 7-mercaptoheptanoylthreonine phosphate: component B of the methylcoenzyme M methylreductase system of Methanobacterium thermoautotrophicum; structure given in first source	1.99	1	0	L-threonine derivative	coenzyme
phosphorus Phosphorus: A non-metal element that has the atomic symbol P, atomic number 15, and atomic weight 31. It is an essential element that takes part in a broad variety of biochemical reactions.	3.09	5	0	monoatomic phosphorus; nonmetal atom; pnictogen	macronutrient
naphthylvinylpyridine Naphthylvinylpyridine: 4(1-Naphthylvinyl)pyridine hydrochloride. Cholinesterase inhibitor. Synonym: YuB 25.	2.38	2	0
cefuroxime [no description available]	2.08	1	0	3-(carbamoyloxymethyl)cephalosporin; furans; oxime O-ether	drug allergen
3-hydroxyamino-1-methyl-5h-pyrido(4,3-b)indole 3-hydroxyamino-1-methyl-5H-pyrido(4,3-b)indole: active metabolite of potent mutagen Trp-P-2	2.37	2	0
oleoyl-coenzyme a oleoyl-coenzyme A: RN given refers to (Z)-isomer	2.38	2	0	octadecenoyl-CoA	Escherichia coli metabolite; mouse metabolite
n-acetylsphingosine N-acetylsphingosine: inhibits phospholipase D. N-acetylsphingosine : A N-acylsphingosine that has an acetamido group at position 2.	2.25	1	0	N-acylsphingosine
crotonyl-coenzyme a crotonoyl-CoA : The (E)-isomer of but-2-enoyl-CoA.	4.66	8	0	but-2-enoyl-CoA
docosapentaenoic acid docosapentaenoic acid : Any straight-chain, C22 fatty acid having five C=C double bonds.. (7Z,10Z,13Z,16Z,19Z)-docosapentaenoic acid : The all-cis-isomer of a C22 polyunsaturated fatty acid having five double bonds in the 7-, 10-, 13-, 16- and 19-positions.	2	1	0	docosapentaenoic acid; omega-3 fatty acid	algal metabolite; human metabolite
cefotaxime Cefotaxime: Semisynthetic broad-spectrum cephalosporin.. cefotaxime : A cephalosporin compound having acetoxymethyl and [2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino side groups.	2.08	1	0	1,3-thiazoles; cephalosporin; oxime O-ether	antibacterial drug; drug allergen
germacrene a germacrene A: RN given for (S-(E,E))-isomer; structure in first source	2.6	1	0	germacrene; sesquiterpene
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.	3.82	12	0	ammonium salt; inorganic sulfate salt	fertilizer
bisabolol bisabolol: monocyclic sesquiterpene alcohol with strong bacteriocidal effects, especilly against M. Tuberc.; isolated from seed plant Populus tacamacaha; RN given refers to cpd without isomeric desigation	2.21	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.	1.95	1	0	chalcogen; nonmetal atom	micronutrient
oxalates Oxalates: Derivatives of OXALIC ACID. Included under this heading are a broad variety of acid forms, salts, esters, and amides that are derived from the ethanedioic acid structure.	3.47	8	0
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.	1.95	1	0	amidobenzoic acid
dolichols Dolichols: A class of polyprenols which contain approximately 20 isoprene residues. Although considered ISOPRENOIDS, they terminate with an alpha-saturated isoprenoid group at the hydroxy end of the molecule.	3.51	2	0	polyterpene
n,n',n''-triacetylfusarinine c N,N',N''-triacetylfusarinine C: from Mycelia sterilia; ferric ionophore for this organism; structure given in first source	2.06	1	0	iron coordination entity; organonitrogen compound
2-cyano-3-(1-phenylindol-3-yl)acrylate 2-cyano-3-(1-phenylindol-3-yl)acrylate: inhibits pyruvate transport into mitochondria	2.15	1	0
4-coumaroyl-coenzyme a 4-coumaroyl-coenzyme A: structure given in first source. trans-4-coumaroyl-CoA : A 4-coumaroyl-CoA in which the double bond of the coumaroyl group has trans-geochemistry.. 4-coumaroyl-CoA : The S-(4-coumaroyl) derivative of coenzyme A.	2.03	1	0	4-coumaroyl-CoA
antibiotic 1233a antibiotic 1233A: beta-lactone antibiotic from Cephalosporium; hydroxymethylglutaryl-CoA synthase & 3C protease, viral inhibitor; structure in first source	2.38	2	0	long-chain fatty acid
tiglylglycine tiglylglycine: RN is from 9th CI. tiglylglycine : An N-acylglycine that is glycine with an amine hydrogen substituted by a 2-methylbut-2-enoyl (tiglyl) group.	1.96	1	0	N-acylglycine	metabolite
cinnamoyl-coenzyme a (E)-cinnamoyl-CoA : The (E)-isomer of cinnamoyl-CoA.	1.99	1	0	cinnamoyl-CoA
vernoleate vernolic acid : A monounsaturated epoxy fatty acid composed of cis-9-octadecenoic acid having a 12,13-epoxy group.. (+)-vernolic acid : An optically active form of vernolic acid having (12S,13R)-configuration.	2.03	1	0	oxylipin; vernolic acid
ganglioside, gd2 [no description available]	1.98	1	0
i(3)so3-galactosylceramide Sulfoglycosphingolipids: GLYCOSPHINGOLIPIDS with a sulfate group esterified to one of the sugar groups.. 1-(3-O-sulfo-beta-D-galactosyl)-N-tetracosanoylsphingosine : A D-galactosyl-N-acylsphingosine having a sulfo group at the 3-position on the galactose ring and tetracosanoyl as the N-acyl group.	2.35	2	0	galactosylceramide sulfate; N-acyl-beta-D-galactosylsphingosine
ergoline Ergolines: A series of structurally-related alkaloids that contain the ergoline backbone structure.. ergoline : An indole alkaloid whose structural skeleton is found in many naturally occurring and synthetic ergolines which are known to bind to neurotransmitter receptors, such as dopamine, noradrenaline and serotonin receptors and function as unselective agonists or antagonists at these receptors.	1.98	1	0	diamine; ergoline alkaloid; indole alkaloid fundamental parent; indole alkaloid; organic heterotetracyclic compound
beta-elemene beta-elemene: increases tumor cell immunogenicity by inducing, at least in part, elevated expression of heat shock protein 70 on tumor cell surface. beta-elemene : A sesquiterpene that consists of cyclohexane bearing methyl and vinyl substituents at position 1 as well as two isopropenyl substituents at positions 2 and 4.. (-)-beta-elemene : The (-)-enantiomer of beta-elemene that has (1S,2S,4R)-configuration.	2.6	1	0	beta-elemene	antineoplastic agent
bromopyruvate [no description available]	3.07	5	0	2-oxo monocarboxylic acid anion
aminomethyltransferase Aminomethyltransferase: A one-carbon group transferase that transfers lipoamide-linked methylamine groups to tetrahydrofolate (TETRAHYDROFOLATES) to form methylenetetrahydrofolate and AMMONIA. It is one of four components of the glycine decarboxylase complex.	2.25	1	0
1-deoxy-2-pentulose [no description available]	1.99	1	0	deoxypentose	Escherichia coli metabolite
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.	7.84	13	3	phosphagen; phosphoamino acid	human metabolite; mouse metabolite
etomoxir [no description available]	1.98	1	0	aromatic ether
pentagastrin Pentagastrin: A synthetic pentapeptide that has effects like gastrin when given parenterally. It stimulates the secretion of gastric acid, pepsin, and intrinsic factor, and has been used as a diagnostic aid.	1.95	1	0	organic molecular entity
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.	2.1	1	0	aromatic amide; lactam; monocarboxylic acid amide; morpholines; organochlorine compound; oxazolidinone; thiophenes	anticoagulant; EC 3.4.21.6 (coagulation factor Xa) inhibitor
lipid a Lipid A: Lipid A is the biologically active component of lipopolysaccharides. It shows strong endotoxic activity and exhibits immunogenic properties.. lipid A : The glycolipid moiety of bacterial lipopolysaccharide (R can be either hydrogen or a fatty acyl group).	7.42	2	0	dodecanoate ester; lipid A; tetradecanoate ester	Escherichia coli metabolite
4-methylene-2-octyl-5-oxofuran-3-carboxylic acid 4-methylene-2-octyl-5-oxofuran-3-carboxylic acid: an anorectic fatty acid synthase inhibitor; structure in first source. (2R,3S)-C75 : A 4-methylidene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid that has 2R,3S-configuration.	2.46	2	0	4-methylidene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid; gamma-lactone
estin geodin: structure given in first source. (+)-geodin : An oxaspiro compound that is 3H,4'H-spiro[[1]benzofuran-2,1'-cyclohexa[2,5]diene]-3,4'-dione substituted by methoxycarbonyl, hydroxy, chloro, methyl, methoxy and chloro groups at positions 2', 4, 5, 6, 6' and 7, respectively. It is a fungal metabolite isolated from Aspergillus terreus and Penicillium glabrum.	2.69	2	0	1-benzofurans; ether; methyl ester; organochlorine compound; oxaspiro compound; phenols	Aspergillus metabolite; Penicillium metabolite
dapagliflozin [no description available]	2.6	1	0	aromatic ether; C-glycosyl compound; monochlorobenzenes	hypoglycemic agent; sodium-glucose transport protein subtype 2 inhibitor
gw 4064 [no description available]	2.15	1	0	stilbenoid
monacolin j monacolin J: isolated from Monascus ruber; structure given in first source. monacolin J : A polyketide that is monacolin L bearing an additional hydroxy substituent at position 8.	2.21	1	0	2-pyranones; carbobicyclic compound; hexahydronaphthalenes; polyketide; secondary alcohol	antimicrobial agent; EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor; fungal metabolite
medigoxin spirotetramat: for the control of a broad spectrum of sucking insects; structure in first source. spirotetramat : An azaspiro compound that is methoxycyclohexane which is fused at position 4 to the 5-position of a 1,5-dihydro-2H-pyrrol-2-one that is substituted at positions 3 and 4 by 2,5-dimethylphenyl and (ethoxycarbonyl)oxy groups, respectively (the cis isomer). It is a proinsecticide (via hydrolysis of the ethyl carbonate group to give the corresponding 4-hydroxypyrrol-2-one, "spirotetramat-enol") and is used for the control of a wide range of sucking insects on fruit and potato crops.	2.15	1	0
n-hexanoyl-l-homoserine lactone N-hexanoyl-L-homoserine lactone: structure in first source	1.99	1	0	N-acyl-amino acid
holomycin holomycin: structure. holomycin : A dithiolopyrrolone antibiotic that is 4,5-dihydro[1,2]dithiolo[4,3-b]pyrrole in which the hydrogens at positions 5 and 6 have been replaced by oxo and acetamido groups, respectively. It is an inhibitor of DNA-dependent RNA polymerase, and exhibits antibacterial and antitumour properties.	2.07	1	0	acetamides; dithiolopyrrolone antibiotic	antibacterial agent; antineoplastic agent; bacterial metabolite; chelator; EC 2.7.7.6 (RNA polymerase) inhibitor; marine metabolite
sb 204990 [no description available]	2.02	1	0
n-pentylpantothenamide N-pentylpantothenamide: converted to ethyldethia-coenzyme A, an antimetabolite; structure in first source	2.47	2	0
ribose ribopyranose : The pyranose form of ribose.	2.06	1	0	D-ribose; ribopyranose
acebutolol alpha-D-glucosyl-(1->4)-alpha-D-mannose : An alpha-D-glucosyl-(1->4)-D-mannopyranose in which the anomeric hydroxy group has alpha configuration.	2.4	2	0	alpha-D-glucosyl-(1->4)-D-mannopyranose
dorsomorphin dorsomorphin: an AMPK inhibitor. dorsomorphin : A pyrazolopyrimidine that is pyrazolo[1,5-a]pyrimidine which is substituted at positions 3 and 6 by pyridin-4-yl and p-[2-(piperidin-1-yl)ethoxy]phenyl groups, respectively. It is a potent, selective, reversible, and ATP-competitive inhibitor of AMPK (AMP-activated protein kinase, EC 2.7.11.31) and a selective inhibitor of bone morphogenetic protein (BMP) signaling.	2.08	1	0	aromatic ether; piperidines; pyrazolopyrimidine; pyridines	bone morphogenetic protein receptor antagonist; EC 2.7.11.31 {[hydroxymethylglutaryl-CoA reductase (NADPH)] kinase} inhibitor
azinomycin a azinomycin A: from Streptomyces griseofuscus S42227; structure given in first source; (but Biochemistry. 2000 Dec 5;39(48):14968-75 says Azinomycin B = carzinophilin A)	2.15	1	0
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).	2.88	4	0	O-palmitoylcarnitine; saturated fatty acyl-L-carnitine	EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; human metabolite; mouse metabolite
dihydromonacolin l dihydromonacolin L: isolated from Monaseus ruber; MF: C19-H30-O3; structure given in first source. dihydromonacolin L : A pyranone obtained by selective hydrogenation of the 4a,5-double bond in monacolin L.	2.21	1	0	2-pyranones; octahydronaphthalenes
calcimycin Calcimycin: An ionophorous, polyether antibiotic from Streptomyces chartreusensis. It binds and transports CALCIUM and other divalent cations across membranes and uncouples oxidative phosphorylation while inhibiting ATPase of rat liver mitochondria. The substance is used mostly as a biochemical tool to study the role of divalent cations in various biological systems.	3.58	9	0	benzoxazole
valeryl-coenzyme a pentanoyl-CoA : A short-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of pentanoic acid.	2.03	1	0	short-chain fatty acyl-CoA
s-tetradecanoyl-coenzyme a myristoyl-CoA : A long-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of myristic acid.	2.41	1	0	11,12-saturated fatty acyl-CoA; long-chain fatty acyl-CoA	Escherichia coli metabolite; mouse metabolite
4-hydroxybutyryl-coenzyme a 4-hydroxybutyryl-coenzyme A: structure given in first source. 4-hydroxybutyryl-CoA : An acyl-CoA resulting from the formal condensation of the thiol group of coenzyme A with the carboxy group of 4-hydroxybutyric acid.	2.74	3	0	hydroxyacyl-CoA
sepharose agarose : A linear polysaccharide made up from alternating D-galactose and 3,6-anhydro-alpha-L-galactopyranose residues joined by alpha-(1->3)- and beta-(1->4)-linkages.	2.69	3	0
vindoline [no description available]	1.97	1	0
phytosterols Phytosterols: A class of organic compounds known as sterols or STEROIDS derived from plants.. phytosterols : Sterols similar to cholesterol which occur in plants and vary only in carbon side chains and/or presence or absence of a double bond.	1.95	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.	2.38	2	0
azinomycin b azinomycin B: C31H33N3O11; from Streptomyces griseofuscus S42227; structure given in first source	2.15	1	0
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	11.87	186	0	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
cytochrome c-t Cytochromes c: Cytochromes of the c type that are found in eukaryotic MITOCHONDRIA. They serve as redox intermediates that accept electrons from MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX III and transfer them to MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX IV.	3.82	3	0
cholecystokinin Cholecystokinin: A peptide, of about 33 amino acids, secreted by the upper INTESTINAL MUCOSA and also found in the central nervous system. It causes gallbladder contraction, release of pancreatic exocrine (or digestive) enzymes, and affects other gastrointestinal functions. Cholecystokinin may be the mediator of satiety.	1.95	1	0
thymalfasin Thymalfasin: A thymus hormone polypeptide found in thymosin fraction 5 (a crude thymus gland extract) but now produced by synthesis. It is used alone or with interferon as an immunomodulator for the treatment of CHRONIC HEPATITIS B and HEPATITIS C. Thymalfasin is also used for the treatment of chemotherapy-induced immunosuppression, and to enhance the efficacy of influenza and hepatitis B vaccines in immunocompromised patients.	1.96	1	0	polypeptide
humanin humanin: suppresses neuronal cell death induced by the Swedish mutant of amyloid precursor protein; suppresses neuronal cell death induced by three different types of FAD genes and amyloid beta; amino acid sequence in first source	2.15	1	0
glucagon Glucagon: A 29-amino acid pancreatic peptide derived from proglucagon which is also the precursor of intestinal GLUCAGON-LIKE PEPTIDES. Glucagon is secreted by PANCREATIC ALPHA CELLS and plays an important role in regulation of BLOOD GLUCOSE concentration, ketone metabolism, and several other biochemical and physiological processes. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1511). glucagon : A 29-amino acid peptide hormone consisting of His, Ser, Gln, Gly, Thr, Phe, Thr, Ser, Asp, Tyr, Ser, Lys, Tyr, Leu, Asp, Ser, Arg, Arg, Ala, Gln, Asp, Phe, Val, Gln, Trp, Leu, Met, Asn and Thr residues joined in sequence.	5.28	10	0	peptide hormone
oligonucleotides [no description available]	2.07	1	0
anticodon Anticodon: The sequential set of three nucleotides in TRANSFER RNA that interacts with its complement in MESSENGER RNA, the CODON, during translation in the ribosome.	2.05	1	0
cellulose DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.	4.34	5	0	glycoside
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	5.18	9	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.	1.95	1	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.	2.38	2	0	chlorophyll; methyl ester	cofactor
azd 7545 AZD 7545: an anilide tertiary carbinol; a pyruvate dehydrogenase kinase 2 inhibitor. AZD7545 : A sulfone that is benzene substituted by [4-(dimethylcarbamoyl)phenyl]sulfonyl, chloro and [(2R)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoyl]amino groups at positions 1, 3 and 4, respectively. It is a potent and non-ATP-competitive inhibitor of pyruvate dehydrogenase kinase 2 (PDHK2) with IC50 of 6.4 nM and exhibits glucose-lowering activity. Also inhibits PDHK1 at higher levels (IC50 = 36.8 nM).	2.17	1	0	benzamides; monochlorobenzenes; organofluorine compound; secondary carboxamide; sulfone; tertiary alcohol; tertiary carboxamide	EC 2.7.11.2 - [pyruvate dehydrogenase (acetyl-transferring)] kinase inhibitor; hypoglycemic agent
didymin didymin: a dietary glycoside from citrus fruits that induces Fas-mediated apoptotic pathway in human non-small-cell lung cancer cells in vitro and in vivo; structure in first source	2.31	1	0	flavonoids; glycoside
ubiquinone Ubiquinone: A lipid-soluble benzoquinone which is involved in ELECTRON TRANSPORT in mitochondrial preparations. The compound occurs in the majority of aerobic organisms, from bacteria to higher plants and animals.	3.78	3	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.	2.1	1	0
arphamenine a arphamenine A: from Chromobacterium violaceum; structure given in second source	1.96	1	0
chitosan [no description available]	2.31	1	0
perylenequinone perylenequinone: structure in first source	2.41	1	0
n-acetylgalactosamine-1-phosphate N-acetyl-D-galactosamine 1-phosphate : A D-galactosamine 1-phosphate compound having an N-acetyl substituent.	2.05	1	0	D-galactosamine 1-phosphate	human metabolite
mesna Mesna: A sulfhydryl compound used to prevent urothelial toxicity by inactivating metabolites from ANTINEOPLASTIC AGENTS, such as IFOSFAMIDE or CYCLOPHOSPHAMIDE.	4.52	4	0	organosulfonic acid
sodium oxybate Sodium Oxybate: The sodium salt of 4-hydroxybutyric acid. It is used for both induction and maintenance of ANESTHESIA.	2.52	2	0
bucladesine Bucladesine: A cyclic nucleotide derivative that mimics the action of endogenous CYCLIC AMP and is capable of permeating the cell membrane. It has vasodilator properties and is used as a cardiac stimulant. (From Merck Index, 11th ed). bucladesine : A 3',5'-cyclic purine nucleotide that is the 2'-butanoate ester and 6-N-butanoyl derivative of 3',5'-cyclic AMP.	3.22	6	0	3',5'-cyclic purine nucleotide
4-hydroxymercuribenzoate [no description available]	1.96	1	0
stearates Stearates: Salts and esters of the 18-carbon saturated, monocarboxylic acid--stearic acid.	1.95	1	0
s-adenosylmethionine (R)-S-adenosyl-L-methionine : An S-adenosyl-L-methionine that has R-configuration.. S-adenosyl-L-methionine zwitterion : A zwitterionic tautomer of S-adenosyl-L-methionine arising from shift of the proton from the carboxy group to the amino group.. (R)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has R-configuration; major species at pH 7.3.. (S)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has S-configuration; major species at pH 7.3.. S-adenosyl-L-methionine : A sulfonium compound that is the S-adenosyl derivative of L-methionine. It is an intermediate in the metabolic pathway of methionine.	7.09	20	0	organic cation; sulfonium compound	coenzyme; cofactor; human metabolite; micronutrient; Mycoplasma genitalium metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
cpi 613 devimistat: has antineoplastic activity; structure in first source	2.25	1	0
2',3'-o-(2,4,6-trinitrophenyl)adenosine 5'-triphosphate 2',3'-O-(2,4,6-trinitrophenyl)adenosine 5'-triphosphate: analog of ATP; do not confuse with TNP-ATP record	2.53	2	0	C-nitro compound; spiroketal	antagonist
fluorosalinosporamide fluorosalinosporamide: structure in first source	3.21	1	0
egg white Egg White: The white of an egg, especially a chicken's egg, used in cooking. It contains albumin. (Random House Unabridged Dictionary, 2d ed)	1.93	1	0
cardiovascular agents Cardiovascular Agents: Agents that affect the rate or intensity of cardiac contraction, blood vessel diameter, or blood volume.	3.41	1	0
bacillaene bacillaene: an inhibitor of procaryotic protein synthesis; produced by the PksX megacomplex; isolated from Bacillus subtilis; a hexaene with molecular formula C35-H48-O7. bacillaene : A polyene antibiotic obtained from Bacillus subtilis 168 that is active against a broad spectrum of bacteria. It is notoriously unstable.	2.07	1	0	enamine; monocarboxylic acid amide; polyene antibiotic; polyketide; secondary alcohol	antibacterial agent; antimicrobial agent; bacterial metabolite
mannans [no description available]	2.44	2	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.	1.95	1	0
J147 J147: neurotrophic curcumin derivative compound that has enhanced stability and bioavailability over curcumin	2.21	1	0	anilide
glycolipids [no description available]	3.07	5	0
feruloyl-coa feruloyl-CoA(4-) : An acyl-CoA(4-) that is the tetraanion of feruloyl-CoA arising from deprotonation of the phosphate and diphosphate OH groups.. trans-feruloyl-CoA(4-) : An acyl-CoA(4-) obtained by deprotonation of the phosphate and diphosphate OH groups of 3-trans-feruloyl-CoA. Major structure at pH 7.3.	2.04	1	0	feruloyl-CoA(4-)
piperidines Piperidines: A family of hexahydropyridines.	2.4	2	0
thymosin Thymosin: Thymosin. A family of heat-stable, polypeptide hormones secreted by the thymus gland. Their biological activities include lymphocytopoiesis, restoration of immunological competence and enhancement of expression of T-cell characteristics and function. They have therapeutic potential in patients having primary or secondary immunodeficiency diseases, cancer or diseases related to aging.	1.96	1	0
bm 42304 [no description available]	1.96	1	0
hydroxocobalamin Hydroxocobalamin: Injectable form of VITAMIN B 12 that has been used therapeutically to treat VITAMIN B 12 DEFICIENCY.	2.06	1	0
jadomycin b jadomycin B: structure given in first source; isolated from Streptomyces venezuelae. jadomycin B : A jadomycin that is jadomycin A in which the phenolic hydroxy group at position 12 has been converted to the corresponding 2,6-dideoxy-alpha-L-ribo-hexopyranoside, isolated from Streptomyces venezuelae. It exists as a diastereoisomeric mixture consisting of both 3aS and 3aR isomers.	2	1	0	glycoside; jadomycin; organic heteropentacyclic compound	antibacterial agent; antineoplastic agent; apoptosis inducer; Aurora kinase inhibitor; bacterial metabolite
uridine diphosphate n-acetylgalactosamine Uridine Diphosphate N-Acetylgalactosamine: A nucleoside diphosphate sugar which serves as a source of N-acetylgalactosamine for glycoproteins, sulfatides and cerebrosides.. UDP-N-acetyl-D-galactosamine(2-) : Dianion of UDP-N-acetyl-D-galactosamine arising from deprotonation of the diphosphate OH groups; major species at pH 7.3.. UDP-N-acetyl-D-galactosamine : A UDP-sugar having N-acetyl-D-galactosamine as the sugar component.	2.11	1	0	nucleotide-sugar oxoanion	human metabolite
methylmalonyl-coenzyme a [no description available]	3.52	8	0
fructose-1,6-diphosphate fructose-1,6-diphosphate: RN refers to (D)-isomer	3.12	5	0
fluoroacetyl-coenzyme a fluoroacetyl-CoA : An acyl-CoA that results from the formal condensation of the thiol group of Co-A with the carboxylic acid group of fluoroacetic acid.	5.04	13	0	haloacyl-CoA
natriuretic peptide, brain Natriuretic Peptide, Brain: A PEPTIDE that is secreted by the BRAIN and the HEART ATRIA, stored mainly in cardiac ventricular MYOCARDIUM. It can cause NATRIURESIS; DIURESIS; VASODILATION; and inhibits secretion of RENIN and ALDOSTERONE. It improves heart function. It contains 32 AMINO ACIDS.	3.16	1	0	polypeptide
heme Heme: The color-furnishing portion of hemoglobin. It is found free in tissues and as the prosthetic group in many hemeproteins.. ferroheme : Any iron(II)--porphyrin coordination complex.. ferroheme b : Heme b in which the iron has oxidation state +2.. heme : A heme is any tetrapyrrolic chelate of iron.	2.03	1	0
2,4-diacetamido-2,4,6-trideoxyglucopyranose [no description available]	2.08	1	0
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	2.66	3	0	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
4-hydroxy-6-methyl-2-pyrone 4-hydroxy-6-methyl-2-pyrone: structure in first source	3.27	6	0	2-pyranones
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.	1.95	1	0
salicylates Salicylates: The salts or esters of salicylic acids, or salicylate esters of an organic acid. Some of these have analgesic, antipyretic, and anti-inflammatory activities by inhibiting prostaglandin synthesis.. hydroxybenzoate : Any benzoate derivative carrying a single carboxylate group and at least one hydroxy substituent.. salicylates : Any salt or ester arising from reaction of the carboxy group of salicylic acid, or any ester resulting from the condensation of the phenolic hydroxy group of salicylic acid with an organic acid.. salicylate : A monohydroxybenzoate that is the conjugate base of salicylic acid.	3.23	6	0	monohydroxybenzoate	plant metabolite
dicumarol Dicumarol: An oral anticoagulant that interferes with the metabolism of vitamin K. It is also used in biochemical experiments as an inhibitor of reductases.	1.96	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.	3.39	7	0	benzenes; hydroxycoumarin; methyl ketone
transforming growth factor beta Transforming Growth Factor beta: A factor synthesized in a wide variety of tissues. It acts synergistically with TGF-alpha in inducing phenotypic transformation and can also act as a negative autocrine growth factor. TGF-beta has a potential role in embryonal development, cellular differentiation, hormone secretion, and immune function. TGF-beta is found mostly as homodimer forms of separate gene products TGF-beta1, TGF-beta2 or TGF-beta3. Heterodimers composed of TGF-beta1 and 2 (TGF-beta1.2) or of TGF-beta2 and 3 (TGF-beta2.3) have been isolated. The TGF-beta proteins are synthesized as precursor proteins.	2.66	2	0
okadaic acid Okadaic Acid: A specific inhibitor of phosphoserine/threonine protein phosphatase 1 and 2a. It is also a potent tumor promoter. It is produced by DINOFLAGELLATES and causes diarrhetic SHELLFISH POISONING.. okadaic acid : A polycyclic ether that is produced by several species of dinoflagellates, and is known to accumulate in both marine sponges and shellfish. A polyketide, polyether derivative of a C38 fatty acid, it is one of the primary causes of diarrhetic shellfish poisoning (DSP). It is a potent inhibitor of specific protein phosphatases and is known to have a variety of negative effects on cells.	1.98	1	0	ketal
ferricrocin ferricrocin: close structural analog of ferrichrome, mediating iron uptake with same rate. ferricrocin : A member of the class of ferrichromes that is an iron(III) chelate of the homodetic cyclic hexapeptide cyclo(glycyl-L-serylglycyl-N(5)-acetyl-N(5)-hydroxy-L-ornithyl-N(5)-acetyl-N(5)-hydroxy-L-ornithyl-N(5)-acetyl-N(5)-hydroxy-L-ornithyl).	2.06	1	0
olivine olivine: sand of primarily magnesium iron silicate, containing low levels of free silica; suggested as a less injurious substitute for silica quartz in foundries; RN in Chemline for unspecified composition: 1317-71-1	2.25	1	0
hirudin Hirudin: A 65-residue polypeptide from LEECHES.	1.96	1	0
formycin triphosphate formycin triphosphate: formycin ATP analog	1.98	1	0
2',3'-(o-(2,4,6-trinitrocyclohexadienylidine))adenosine 5'-diphosphate 2',3'-(O-(2,4,6-trinitrocyclohexadienylidine))adenosine 5'-diphosphate: structure given in first source	2.31	1	0
glutaminase [no description available]	1.95	1	0
cyclin d1 Cyclin D1: Protein encoded by the bcl-1 gene which plays a critical role in regulating the cell cycle. Overexpression of cyclin D1 is the result of bcl-1 rearrangement, a t(11;14) translocation, and is implicated in various neoplasms.	2.05	1	0
ganoderic acid ganoderic acid: from the fruiting body of Ganoderma; structure in first source	2.6	1	0
caseins Caseins: A mixture of related phosphoproteins occurring in milk and cheese. The group is characterized as one of the most nutritive milk proteins, containing all of the common amino acids and rich in the essential ones.	1.95	1	0
oligomycins Oligomycins: A closely related group of toxic substances elaborated by various strains of Streptomyces. They are 26-membered macrolides with lactone moieties and double bonds and inhibit various ATPases, causing uncoupling of phosphorylation from mitochondrial respiration. Used as tools in cytochemistry. Some specific oligomycins are RUTAMYCIN, peliomycin, and botrycidin (formerly venturicidin X).	3.2	6	0
nitrophenols Nitrophenols: PHENOLS carrying nitro group substituents.	2.93	4	0
cobinamide [no description available]	2	1	0
formycin diphosphate formycin diphosphate: analog of ADP	1.98	1	0
ginkgolide b [no description available]	1.98	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.	4.77	10	0
humulin s Insulin, Regular, Human: Regular insulin preparations that contain the HUMAN insulin peptide sequence.. insulin (human) : An insulin that is produced in the pancreas and involved in regulating the metabolism of carbohydrates (particularly glucose) and fats. Commonly thought of as a protein, it consists of two peptide chains, one containing 21 amino acid residues and the other containing 30; the chains are joined together by 2 disulfide bonds. Recombinant insulin is identical to human insulin, but is synthesised by inserting the human insulin gene into E. coli, which then produces insulin for human use. It is used in the treatment of type I and type II diabetes.	3.92	2	0
flavin mononucleotide Flavin Mononucleotide: A coenzyme for a number of oxidative enzymes including NADH DEHYDROGENASE. It is the principal form in which RIBOFLAVIN is found in cells and tissues.	3.22	6	0
digitonin Digitonin: A glycoside obtained from Digitalis purpurea; the aglycone is digitogenin which is bound to five sugars. Digitonin solubilizes lipids, especially in membranes and is used as a tool in cellular biochemistry, and reagent for precipitating cholesterol. It has no cardiac effects.. digitonin : A spirostanyl glycoside that is digitogenin in which the 3-hydroxy group is substituted by a beta-D-glucopyranosyl-(1->3)-beta-D-galactopyranosyl-(1->2)-[beta-D-xylopyranosyl-(1->3)]-beta-D-glucopyranosyl-(1->4)-beta-D-galactopyranosyl group. It is a steroidal saponin isolated from the foxglove plant, Digitalis purpurea. It is used extensively as a mild non-ionic detergent for extracting proteins from membranes for structure and function studies.	3.06	5	0
apyrase Apyrase: A calcium-activated enzyme that catalyzes the hydrolysis of ATP to yield AMP and orthophosphate. It can also act on ADP and other nucleoside triphosphates and diphosphates. EC 3.6.1.5.	2.04	1	0
muramidase Muramidase: A basic enzyme that is present in saliva, tears, egg white, and many animal fluids. It functions as an antibacterial agent. The enzyme catalyzes the hydrolysis of 1,4-beta-linkages between N-acetylmuramic acid and N-acetyl-D-glucosamine residues in peptidoglycan and between N-acetyl-D-glucosamine residues in chitodextrin. EC 3.2.1.17.	2.31	1	0
cyclic gmp Cyclic GMP: Guanosine cyclic 3',5'-(hydrogen phosphate). A guanine nucleotide containing one phosphate group which is esterified to the sugar moiety in both the 3'- and 5'-positions. It is a cellular regulatory agent and has been described as a second messenger. Its levels increase in response to a variety of hormones, including acetylcholine, insulin, and oxytocin and it has been found to activate specific protein kinases. (From Merck Index, 11th ed). 3',5'-cyclic GMP : A 3',5'-cyclic purine nucleotide in which the purine nucleobase is specified as guanidine.	2.96	4	0	3',5'-cyclic purine nucleotide; guanyl ribonucleotide	Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
deoxyguanosine [no description available]	2.96	4	0	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
guanosine diphosphate Guanosine Diphosphate: A guanine nucleotide containing two phosphate groups esterified to the sugar moiety.	2.48	2	0	guanosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	Escherichia coli metabolite; mouse metabolite; uncoupling protein inhibitor
guanosine diphosphate glucose guanosine diphosphate glucose: acts as a source of glucose for cellulose synthesis in some plants; minor descriptor (75-83); on-line & Index Medicus search GUANOSINE DIPHOSPHATE SUGARS (75-83); RN given refers to (alpha-D)-isomer. GDP-alpha-D-glucose : A GDP-D-glucose having alpha-configuration at the anomeric centre.	1.98	1	0	GDP-D-glucose
guanosine diphosphate mannose Guanosine Diphosphate Mannose: A nucleoside diphosphate sugar which can be converted to the deoxy sugar GDPfucose, which provides fucose for lipopolysaccharides of bacterial cell walls. Also acts as mannose donor for glycolipid synthesis.. GDP-D-mannose : A GDP-mannose in which the mannose fragment has D-configuration.. GDP-alpha-D-mannose : The alpha-anomer of GDP-D-mannose.	1.98	1	0	GDP-D-mannose	Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite
guanosine triphosphate Guanosine Triphosphate: Guanosine 5'-(tetrahydrogen triphosphate). A guanine nucleotide containing three phosphate groups esterified to the sugar moiety.	3.6	9	0	guanosine 5'-phosphate; purine ribonucleoside 5'-triphosphate	Escherichia coli metabolite; mouse metabolite; uncoupling protein inhibitor
hypoxanthine [no description available]	3.12	1	0	nucleobase analogue; oxopurine; purine nucleobase	fundamental metabolite
inosine [no description available]	2.45	2	0	inosines; purines D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
inosine triphosphate Inosine Triphosphate: Inosine 5'-(tetrahydrogen triphosphate). An inosine nucleotide containing three phosphate groups esterified to the sugar moiety. Synonym: IRPPP.	2.04	1	0	inosine phosphate; purine ribonucleoside 5'-triphosphate	Escherichia coli metabolite; human metabolite; mouse metabolite
folic acid folcysteine: used to promote fertility in chickens. vitamin B9 : Any B-vitamin that exhibits biological activity against vitamin B9 deficiency. Vitamin B9 refers to the many forms of folic acid and its derivatives, including tetrahydrofolic acid (the active form), methyltetrahydrofolate (the primary form found in blood), methenyltetrahydrofolate, folinic acid amongst others. They are present in abundance in green leafy vegetables, citrus fruits, and animal products. Lack of vitamin B9 leads to anemia, a condition in which the body cannot produce sufficient number of red blood cells. Symptoms of vitamin B9 deficiency include fatigue, muscle weakness, and pale skin.	2.67	3	0	folic acids; N-acyl-amino acid	human metabolite; mouse metabolite; nutrient
5,6,7,8-tetrahydromethanopterin [no description available]	1.97	1	0	tetrahydromethanopterin
rifampin Rifampin: A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)	2.67	3	0	cyclic ketal; hydrazone; N-iminopiperazine; N-methylpiperazine; rifamycins; semisynthetic derivative; zwitterion	angiogenesis inhibitor; antiamoebic agent; antineoplastic agent; antitubercular agent; DNA synthesis inhibitor; EC 2.7.7.6 (RNA polymerase) inhibitor; Escherichia coli metabolite; geroprotector; leprostatic drug; neuroprotective agent; pregnane X receptor agonist; protein synthesis inhibitor
thiolactomycin thiolactomycin: from actinomycetes; structure given in first source	2.68	3	0
forodesine forodesine: structure in first source	2.05	1	0	dihydroxypyrrolidine; pyrrolopyrimidine
5,6,7,8-tetrahydrofolic acid 5,6,7,8-tetrahydrofolic acid: RN given refers to (DL)-isomer	3.31	1	0	tetrahydrofolic acid
trypan blue Trypan Blue: A diazo-naphthalene sulfonate that is widely used as a stain.. trypan blue : An organosulfonate salt that is the tetrasodium salt of 3,3'-[(3,3'-dimethylbiphenyl-4,4'-diyl)didiazene-2,1-diyl]bis(5-amino-4-hydroxynaphthalene-2,7-disulfonic acid).	2.94	4	0
bis(3',5')-cyclic diguanylic acid [no description available]	2.21	1	0	cyclic purine dinucleotide; guanyl ribonucleotide	immunomodulator; signalling molecule
8-hydroxy-2'-deoxyguanosine 8-Hydroxy-2'-Deoxyguanosine: Common oxidized form of deoxyguanosine in which C-8 position of guanine base has a carbonyl group.. 8-hydroxy-2'-deoxyguanosine : Guanosine substituted at the purine 8-position by a hydroxy group. It is used as a biomarker of oxidative DNA damage.	2.55	2	0	guanosines	biomarker
formycins Formycins: Pyrazolopyrimidine ribonucleosides isolated from Nocardia interforma. They are antineoplastic antibiotics with cytostatic properties.	1.98	1	0
5-methyltetrahydrofolate 5-methyltetrahydrofolate : A group of heterocyclic compounds based on the 5-methyl-5,6,7,8-tetrahydropteroic acid skeleton conjugated with one or more L-glutamic acid or L-glutamate units.	4.33	6	0
n-(deoxyguanosin-8-yl)-2-aminofluorene N-(deoxyguanosin-8-yl)-2-aminofluorene : Guanosine substituted at the purine 8-position by a (9H-fluoren-2-yl)amino group.	1.98	1	0	guanosines
dehydroluciferin dehydroluciferin: synthesized from luciferin in a reaction catalyzed by firefly luciferase. dehydroluciferin : A member of the class of 1,3-thiazolemonocarboxylic acids that is 1,3-thiazole-4-carboxylic acid in which the hydrogen at position 2 has been replaced by a 6-hydroxy-1,3-benzothiazol-2-yl group.	2.02	1	0	1,3-thiazolemonocarboxylic acid; benzothiazoles; biaryl; phenols	animal metabolite; luciferin
cholestyramine resin Cholestyramine Resin: A strongly basic anion exchange resin whose main constituent is polystyrene trimethylbenzylammonium Cl(-) anion.	2.87	4	0
eye [no description available]	2.66	3	0
tauromuricholate tauromuricholic acid: RN given refers to (3 alpha,5 beta,6 beta,7 beta)-isomer	2.15	1	0
decanoyl-coenzyme a [no description available]	2.37	2	0
concanavalin a Concanavalin A: A MANNOSE/GLUCOSE binding lectin isolated from the jack bean (Canavalia ensiformis). It is a potent mitogen used to stimulate cell proliferation in lymphocytes, primarily T-lymphocyte, cultures.	2.67	3	0
phosphorus radioisotopes Phosphorus Radioisotopes: Unstable isotopes of phosphorus that decay or disintegrate emitting radiation. P atoms with atomic weights 28-34 except 31 are radioactive phosphorus isotopes.	4.15	5	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.	2.99	4	0
pyrimidinones Pyrimidinones: Heterocyclic compounds known as 2-pyrimidones (or 2-hydroxypyrimidines) and 4-pyrimidones (or 4-hydroxypyrimidines) with the general formula C4H4N2O.	2.05	1	0
filipin Filipin: A complex of polyene antibiotics obtained from Streptomyces filipinensis. Filipin III alters membrane function by interfering with membrane sterols, inhibits mitochondrial respiration, and is proposed as an antifungal agent. Filipins I, II, and IV are less important.	1.96	1	0
phenanthrenes Phenanthrenes: POLYCYCLIC AROMATIC HYDROCARBONS composed of three fused BENZENE rings.. phenanthrenes : Any benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof.	2.39	2	0

Condition	Relationship Strength	Studies	Trials
Hepatocellular Carcinoma [description not available]	6.38	27	0
Cancer of Liver [description not available]	6.8	40	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.	6.38	27	0
Liver Neoplasms Tumors or cancer of the LIVER.	6.8	40	0
Benign Neoplasms [description not available]	10.84	60	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.	10.84	60	0
Dominant Hereditary Sensory Neuropathy, Type III [description not available]	2.31	1	0
Dysautonomia, Familial An autosomal disorder of the peripheral and autonomic nervous systems limited to individuals of Ashkenazic Jewish descent. Clinical manifestations are present at birth and include diminished lacrimation, defective thermoregulation, orthostatic hypotension (HYPOTENSION, ORTHOSTATIC), fixed pupils, excessive SWEATING, loss of pain and temperature sensation, and absent reflexes. Pathologic features include reduced numbers of small diameter peripheral nerve fibers and autonomic ganglion neurons. (From Adams et al., Principles of Neurology, 6th ed, p1348; Nat Genet 1993;4(2):160-4)	2.31	1	0
Benign Neoplasms, Brain [description not available]	4.79	11	0
Astrocytoma, Grade IV [description not available]	5.98	8	0
Glial Cell Tumors [description not available]	3.24	5	0
Brain Neoplasms Neoplasms of the intracranial components of the central nervous system, including the cerebral hemispheres, basal ganglia, hypothalamus, thalamus, brain stem, and cerebellum. Brain neoplasms are subdivided into primary (originating from brain tissue) and secondary (i.e., metastatic) forms. Primary neoplasms are subdivided into benign and malignant forms. In general, brain tumors may also be classified by age of onset, histologic type, or presenting location in the brain.	4.79	11	0
Glioblastoma A malignant form of astrocytoma histologically characterized by pleomorphism of cells, nuclear atypia, microhemorrhage, and necrosis. They may arise in any region of the central nervous system, with a predilection for the cerebral hemispheres, basal ganglia, and commissural pathways. Clinical presentation most frequently occurs in the fifth or sixth decade of life with focal neurologic signs or seizures.	5.98	8	0
Glioma Benign and malignant central nervous system neoplasms derived from glial cells (i.e., astrocytes, oligodendrocytes, and ependymocytes). Astrocytes may give rise to astrocytomas (ASTROCYTOMA) or glioblastoma multiforme (see GLIOBLASTOMA). Oligodendrocytes give rise to oligodendrogliomas (OLIGODENDROGLIOMA) and ependymocytes may undergo transformation to become EPENDYMOMA; CHOROID PLEXUS NEOPLASMS; or colloid cysts of the third ventricle. (From Escourolle et al., Manual of Basic Neuropathology, 2nd ed, p21)	3.24	5	0
Hospital-Acquired Condition [description not available]	3.23	1	0
Lassitude [description not available]	2.45	2	0
Complication, Postoperative [description not available]	2.41	1	0
Fatigue The state of weariness following a period of exertion, mental or physical, characterized by a decreased capacity for work and reduced efficiency to respond to stimuli.	2.45	2	0
Postoperative Complications Pathologic processes that affect patients after a surgical procedure. They may or may not be related to the disease for which the surgery was done, and they may or may not be direct results of the surgery.	2.41	1	0
Acidemia Propionic [description not available]	2.41	1	0
Hyperammonemia Elevated level of AMMONIA in the blood. It is a sign of defective CATABOLISM of AMINO ACIDS or ammonia to UREA.	2.84	3	0
Propionic Acidemia Autosomal recessive metabolic disorder caused by mutations in PROPIONYL-COA CARBOXYLASE genes that result in dysfunction of branch chain amino acids and of the metabolism of certain fatty acids. Neonatal clinical onset is characterized by severe metabolic acidemia accompanied by hyperammonemia, HYPERGLYCEMIA, lethargy, vomiting, HYPOTONIA; and HEPATOMEGALY. Survivors of the neonatal onset propionic acidemia often show developmental retardation, and intolerance to dietary proteins. Late-onset form of the disease shows mild mental and/or developmental retardation, sometimes without metabolic acidemia.	2.41	1	0
Cardiovascular Stroke [description not available]	3.62	3	0
Myocardial Infarction NECROSIS of the MYOCARDIUM caused by an obstruction of the blood supply to the heart (CORONARY CIRCULATION).	3.62	3	0
Arthritis, Degenerative [description not available]	2.41	1	0
Osteoarthritis A progressive, degenerative joint disease, the most common form of arthritis, especially in older persons. The disease is thought to result not from the aging process but from biochemical changes and biomechanical stresses affecting articular cartilage. In the foreign literature it is often called osteoarthrosis deformans.	2.41	1	0
Metastase [description not available]	4.61	5	0
Colorectal Cancer [description not available]	3.52	7	0
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	4.61	5	0
Colorectal Neoplasms Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.	3.52	7	0
Lung Adenocarcinoma [description not available]	2.9	2	0
Cancer of Lung [description not available]	3.73	8	0
Adenocarcinoma of Lung A carcinoma originating in the lung and the most common lung cancer type in never-smokers. Malignant cells exhibit distinct features such as glandular epithelial, or tubular morphology. Mutations in KRAS, EGFR, BRAF, and ERBB2 genes are associated with this cancer.	2.9	2	0
Lung Neoplasms Tumors or cancer of the LUNG.	3.73	8	0
Acute Brain Injuries [description not available]	2.82	3	0
Hemorrhage, Subarachnoid [description not available]	2.41	1	0
Brain Injuries Acute and chronic (see also BRAIN INJURIES, CHRONIC) injuries to the brain, including the cerebral hemispheres, CEREBELLUM, and BRAIN STEM. Clinical manifestations depend on the nature of injury. Diffuse trauma to the brain is frequently associated with DIFFUSE AXONAL INJURY or COMA, POST-TRAUMATIC. Localized injuries may be associated with NEUROBEHAVIORAL MANIFESTATIONS; HEMIPARESIS, or other focal neurologic deficits.	2.82	3	0
Subarachnoid Hemorrhage Bleeding into the intracranial or spinal SUBARACHNOID SPACE, most resulting from INTRACRANIAL ANEURYSM rupture. It can occur after traumatic injuries (SUBARACHNOID HEMORRHAGE, TRAUMATIC). Clinical features include HEADACHE; NAUSEA; VOMITING, nuchal rigidity, variable neurological deficits and reduced mental status.	2.41	1	0
Obesity A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).	6.28	22	0
Autism Spectrum Disorder Wide continuum of associated cognitive and neurobehavioral disorders, including, but not limited to, three core-defining features: impairments in socialization, impairments in verbal and nonverbal communication, and restricted and repetitive patterns of behaviors. (from DSM-V)	2.9	3	0
Autism [description not available]	2.41	1	0
Autistic Disorder A disorder beginning in childhood. It is marked by the presence of markedly abnormal or impaired development in social interaction and communication and a markedly restricted repertoire of activity and interest. Manifestations of the disorder vary greatly depending on the developmental level and chronological age of the individual. (DSM-V)	2.41	1	0
Degenerative Diseases, Central Nervous System [description not available]	5.15	7	0
Hallervorden-Spatz Disease [description not available]	2.63	2	0
Pantothenate Kinase-Associated Neurodegeneration A rare autosomal recessive degenerative disorder which usually presents in late childhood or adolescence. Clinical manifestations include progressive MUSCLE SPASTICITY; hyperreflexia; MUSCLE RIGIDITY; DYSTONIA; DYSARTHRIA; and intellectual deterioration which progresses to severe dementia over several years. (From Adams et al., Principles of Neurology, 6th ed, p972; Davis & Robertson, Textbook of Neuropathology, 2nd ed, pp972-929)	2.63	2	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.	5.15	7	0
Diseases of Immune System [description not available]	2.41	1	0
Immune System Diseases Disorders caused by abnormal or absent immunologic mechanisms, whether humoral, cell-mediated, or both.	2.41	1	0
Idiopathic Parkinson Disease [description not available]	2.41	1	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)	2.41	1	0
ER-Negative PR-Negative HER2-Negative Breast Cancer [description not available]	2.89	3	0
Triple Negative Breast Neoplasms Breast neoplasms that do not express ESTROGEN RECEPTORS; PROGESTERONE RECEPTORS; and do not overexpress the NEU RECEPTOR/HER-2 PROTO-ONCOGENE PROTEIN.	2.89	3	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	5.38	23	0
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	7.45	47	0
Carcinogenesis The origin, production or development of cancer through genotypic and phenotypic changes which upset the normal balance between cell proliferation and cell death. Carcinogenesis generally requires a constellation of steps, which may occur quickly or over a period of many years.	5.94	19	0
Fatty Liver, Nonalcoholic [description not available]	5.58	13	0
Non-alcoholic Fatty Liver Disease Fatty liver finding without excessive ALCOHOL CONSUMPTION.	5.58	13	0
Anoxemia [description not available]	7.69	16	1
Hypoxia Sub-optimal OXYGEN levels in the ambient air of living organisms.	7.69	16	1
Mental Retardation, X-Linked A class of genetic disorders resulting in INTELLECTUAL DISABILITY that is associated either with mutations of GENES located on the X CHROMOSOME or aberrations in the structure of the X chromosome (SEX CHROMOSOME ABERRATIONS).	2.41	1	0
Neoplastic Processes The pathological mechanisms and forms taken by tissue during degeneration into a neoplasm and its subsequent activity.	2.41	1	0
Hyperglycemia, Postprandial Abnormally high BLOOD GLUCOSE level after a meal.	3.83	10	0
Cancer of Pancreas [description not available]	3.57	7	0
Hyperglycemia Abnormally high BLOOD GLUCOSE level.	3.83	10	0
Pancreatic Neoplasms Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).	3.57	7	0
Hypergonadotropic Hypogonadism [description not available]	3.9	3	0
Insulin Sensitivity [description not available]	7.5	23	0
Acetonemia [description not available]	5.45	9	0
Hypogonadism Condition resulting from deficient gonadal functions, such as GAMETOGENESIS and the production of GONADAL STEROID HORMONES. It is characterized by delay in GROWTH, germ cell maturation, and development of secondary sex characteristics. Hypogonadism can be due to a deficiency of GONADOTROPINS (hypogonadotropic hypogonadism) or due to primary gonadal failure (hypergonadotropic hypogonadism).	3.9	3	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.	7.5	23	0
Iron Overload An excessive accumulation of iron in the body due to a greater than normal absorption of iron from the gastrointestinal tract or from parenteral injection. This may arise from idiopathic hemochromatosis, excessive iron intake, chronic alcoholism, certain types of refractory anemia, or transfusional hemosiderosis. (From Churchill's Illustrated Medical Dictionary, 1989)	2.41	1	0
Diabetes Mellitus, Adult-Onset [description not available]	7.19	17	0
Diabetes Mellitus, Type 2 A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.	7.19	17	0
Cardiovascular Diseases Pathological conditions involving the CARDIOVASCULAR SYSTEM including the HEART; the BLOOD VESSELS; or the PERICARDIUM.	4.7	4	0
Symptom Cluster [description not available]	2.41	1	0
Syndrome A characteristic symptom complex.	2.41	1	0
Infections, Legionella pneumophila [description not available]	2.41	1	0
Autoimmune Disease [description not available]	3.57	2	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	6.87	43	0
Acute Bacterial Prostatitis [description not available]	2.41	1	0
Pelvic Pain Pain in the pelvic region of genital and non-genital origin.	2.41	1	0
Autoimmune Diseases Disorders that are characterized by the production of antibodies that react with host tissues or immune effector cells that are autoreactive to endogenous peptides.	3.57	2	0
Depression Depressive states usually of moderate intensity in contrast with MAJOR DEPRESSIVE DISORDER present in neurotic and psychotic disorders.	2.61	2	0
Prostatitis Infiltration of inflammatory cells into the parenchyma of PROSTATE. The subtypes are classified by their varied laboratory analysis, clinical presentation and response to treatment.	2.41	1	0
Dehydration The condition that results from excessive loss of water from a living organism.	2.4	2	0
Genetic Predisposition [description not available]	2.78	3	0
EBV Infections [description not available]	2.41	1	0
Epstein-Barr Virus Infections Infection with human herpesvirus 4 (HERPESVIRUS 4, HUMAN); which may facilitate the development of various lymphoproliferative disorders. These include BURKITT LYMPHOMA (African type), INFECTIOUS MONONUCLEOSIS, and oral hairy leukoplakia (LEUKOPLAKIA, HAIRY).	2.41	1	0
Alloxan Diabetes [description not available]	4.45	23	0
Liver Steatosis [description not available]	5.11	15	0
Fatty Liver Lipid infiltration of the hepatic parenchymal cells resulting in a yellow-colored liver. The abnormal lipid accumulation is usually in the form of TRIGLYCERIDES, either as a single large droplet or multiple small droplets. Fatty liver is caused by an imbalance in the metabolism of FATTY ACIDS.	5.11	15	0
Deficiency, Thiamine [description not available]	4.4	8	0
Thiamine Deficiency A nutritional condition produced by a deficiency of THIAMINE in the diet, characterized by anorexia, irritability, and weight loss. Later, patients experience weakness, peripheral neuropathy, headache, and tachycardia. In addition to being caused by a poor diet, thiamine deficiency in the United States most commonly occurs as a result of alcoholism, since ethanol interferes with thiamine absorption. In countries relying on polished rice as a dietary staple, BERIBERI prevalence is very high. (From Cecil Textbook of Medicine, 19th ed, p1171)	4.4	8	0
Weight Reduction [description not available]	2.99	4	0
Weight Loss Decrease in existing BODY WEIGHT.	2.99	4	0
Alcoholic Liver Diseases [description not available]	2.6	1	0
Alcoholic Fatty Liver [description not available]	2.6	1	0
Liver Diseases, Alcoholic Liver diseases associated with ALCOHOLISM. It usually refers to the coexistence of two or more subentities, i.e., ALCOHOLIC FATTY LIVER; ALCOHOLIC HEPATITIS; and ALCOHOLIC CIRRHOSIS.	2.6	1	0
2019 Novel Coronavirus Disease [description not available]	2.6	1	0
Koch's Disease [description not available]	2.84	3	0
Tuberculosis Any of the infectious diseases of man and other animals caused by species of MYCOBACTERIUM TUBERCULOSIS.	2.84	3	0
Hyperlipemia [description not available]	5.79	8	1
Hyperlipidemias Conditions with excess LIPIDS in the blood.	5.79	8	1
Acute Confusional Senile Dementia [description not available]	7.29	17	0
Alzheimer Disease A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)	7.29	17	0
Malignant Melanoma [description not available]	2.72	3	0
Melanoma A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)	2.72	3	0
Chronic Kidney Diseases [description not available]	2.6	1	0
Cachexia General ill health, malnutrition, and weight loss, usually associated with chronic disease.	2.43	2	0
Renal Insufficiency, Chronic Conditions in which the KIDNEYS perform below the normal level for more than three months. Chronic kidney insufficiency is classified by five stages according to the decline in GLOMERULAR FILTRATION RATE and the degree of kidney damage (as measured by the level of PROTEINURIA). The most severe form is the end-stage renal disease (CHRONIC KIDNEY FAILURE). (Kidney Foundation: Kidney Disease Outcome Quality Initiative, 2002)	2.6	1	0
Cognitive Decline [description not available]	2.6	1	0
Cognitive Dysfunction Diminished or impaired mental and/or intellectual function.	2.6	1	0
Cardiac Remodeling, Ventricular [description not available]	2.61	2	0
Cardiac Failure [description not available]	8.28	18	0
Heart Failure A heterogeneous condition in which the heart is unable to pump out sufficient blood to meet the metabolic need of the body. Heart failure can be caused by structural defects, functional abnormalities (VENTRICULAR DYSFUNCTION), or a sudden overload beyond its capacity. Chronic heart failure is more common than acute heart failure which results from sudden insult to cardiac function, such as MYOCARDIAL INFARCTION.	8.28	18	0
T-Cell Lymphoma [description not available]	2.6	1	0
Lymphoma, T Cell, Peripheral [description not available]	2.6	1	0
Lymphoma, T-Cell A group of heterogeneous lymphoid tumors representing malignant transformations of T-lymphocytes.	2.6	1	0
Lymphoma, T-Cell, Peripheral A group of malignant lymphomas thought to derive from peripheral T-lymphocytes in lymph nodes and other nonlymphoid sites. They include a broad spectrum of lymphocyte morphology, but in all instances express T-cell markers admixed with epithelioid histiocytes, plasma cells, and eosinophils. Although markedly similar to large-cell immunoblastic lymphoma (LYMPHOMA, LARGE-CELL, IMMUNOBLASTIC), this group's unique features warrant separate treatment.	2.6	1	0
Breast Cancer [description not available]	4.84	12	0
Breast Neoplasms Tumors or cancer of the human BREAST.	4.84	12	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.	4.41	8	0
Innate Inflammatory Response [description not available]	5.13	15	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.	5.13	15	0
Starvation Lengthy and continuous deprivation of food. (Stedman, 25th ed)	8.05	30	0
Local Neoplasm Recurrence [description not available]	2.6	1	0
Age-Related Memory Disorders [description not available]	3.34	2	0
Memory Disorders Disturbances in registering an impression, in the retention of an acquired impression, or in the recall of an impression. Memory impairments are associated with DEMENTIA; CRANIOCEREBRAL TRAUMA; ENCEPHALITIS; ALCOHOLISM (see also ALCOHOL AMNESTIC DISORDER); SCHIZOPHRENIA; and other conditions.	3.34	2	0
Disease Resistance The capacity of an organism to defend itself against pathological processes or the agents of those processes. This most often involves innate immunity whereby the organism responds to pathogens in a generic way. The term disease resistance is used most frequently when referring to plants.	2.21	1	0
Parasitemia The presence of parasites (especially malarial parasites) in the blood. (Dorland, 27th ed)	2.21	1	0
Plasmodium falciparum Malaria [description not available]	2.66	2	0
Malaria, Falciparum Malaria caused by PLASMODIUM FALCIPARUM. This is the severest form of malaria and is associated with the highest levels of parasites in the blood. This disease is characterized by irregularly recurring febrile paroxysms that in extreme cases occur with acute cerebral, renal, or gastrointestinal manifestations.	2.66	2	0
Cryptogenic Fibrosing Alveolitis [description not available]	2.21	1	0
Idiopathic Pulmonary Fibrosis A common interstitial lung disease of unknown etiology, usually occurring between 50-70 years of age. Clinically, it is characterized by an insidious onset of breathlessness with exertion and a nonproductive cough, leading to progressive DYSPNEA. Pathological features show scant interstitial inflammation, patchy collagen fibrosis, prominent fibroblast proliferation foci, and microscopic honeycomb change.	2.21	1	0
Inborn Errors of Metabolism [description not available]	4.96	6	0
Metabolism, Inborn Errors Errors in metabolic processes resulting from inborn genetic mutations that are inherited or acquired in utero.	4.96	6	0
Acute Myelogenous Leukemia [description not available]	2.87	3	0
Leukemia, Myeloid, Acute Clonal expansion of myeloid blasts in bone marrow, blood, and other tissue. Myeloid leukemias develop from changes in cells that normally produce NEUTROPHILS; BASOPHILS; EOSINOPHILS; and MONOCYTES.	2.87	3	0
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	7.61	31	0
Encephalopathy, Traumatic [description not available]	2.21	1	0
Brain Injuries, Traumatic A form of acquired brain injury which occurs when a sudden trauma causes damage to the brain.	2.21	1	0
Alcohol Drinking Behaviors associated with the ingesting of ALCOHOLIC BEVERAGES, including social drinking.	2.73	3	0
Viral Diseases [description not available]	3.12	1	0
Virus Diseases A general term for diseases caused by viruses.	3.12	1	0
Impaired Glucose Tolerance [description not available]	4.37	2	0
Enlarged Liver [description not available]	2.25	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.	4.37	2	0
Metabolic Acidosis [description not available]	4.61	6	0
Cancer of Kidney [description not available]	3.92	4	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.	4.61	6	0
Kidney Neoplasms Tumors or cancers of the KIDNEY.	3.92	4	0
Aerobic Glycolysis, Oncologic [description not available]	3.6	2	0
Liver Dysfunction [description not available]	4.33	4	0
Liver Diseases Pathological processes of the LIVER.	4.33	4	0
African Sleeping Sickness [description not available]	2.25	1	0
Trypanosomiasis, African A disease endemic among people and animals in Central Africa. It is caused by various species of trypanosomes, particularly T. gambiense and T. rhodesiense. Its second host is the TSETSE FLY. Involvement of the central nervous system produces African sleeping sickness. Nagana is a rapidly fatal trypanosomiasis of horses and other animals.	2.25	1	0
Menopause The last menstrual period. Permanent cessation of menses (MENSTRUATION) is usually defined after 6 to 12 months of AMENORRHEA in a woman over 45 years of age. In the United States, menopause generally occurs in women between 48 and 55 years of age.	2.25	1	0
Cardiometabolic Syndrome A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components not only include metabolic dysfunctions of METABOLIC SYNDROME but also HYPERTENSION, and ABDOMINAL OBESITY.	2.89	3	0
Metabolic Syndrome A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components of metabolic syndrome include ABDOMINAL OBESITY; atherogenic DYSLIPIDEMIA; HYPERTENSION; HYPERGLYCEMIA; INSULIN RESISTANCE; a proinflammatory state; and a prothrombotic (THROMBOSIS) state.	2.89	3	0
Alveolitis, Fibrosing [description not available]	2.25	1	0
Pulmonary Fibrosis A process in which normal lung tissues are progressively replaced by FIBROBLASTS and COLLAGEN causing an irreversible loss of the ability to transfer oxygen into the bloodstream via PULMONARY ALVEOLI. Patients show progressive DYSPNEA finally resulting in death.	2.25	1	0
Endotoxemia A condition characterized by the presence of ENDOTOXINS in the blood. On lysis, the outer cell wall of gram-negative bacteria enters the systemic circulation and initiates a pathophysiologic cascade of pro-inflammatory mediators.	2.25	1	0
Cirrhosis [description not available]	3.83	3	0
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	3.83	3	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)	3.17	1	0
Nasopharyngeal Carcinoma A carcinoma that originates in the EPITHELIUM of the NASOPHARYNX and includes four subtypes: keratinizing squamous cell, non-keratinizing, basaloid squamous cell, and PAPILLARY ADENOCARCINOMA. It is most prevalent in Southeast Asian populations and is associated with EPSTEIN-BARR VIRUS INFECTIONS. Somatic mutations associated with this cancer have been identified in NPCR, BAP1, UBAP1, ERBB2, ERBB3, MLL2, PIK3CA, KRAS, NRAS, and ARID1A genes.	2.25	1	0
Chronic Pancreatitis [description not available]	2.31	1	0
Pancreatitis, Chronic INFLAMMATION of the PANCREAS that is characterized by recurring or persistent ABDOMINAL PAIN with or without STEATORRHEA or DIABETES MELLITUS. It is characterized by the irregular destruction of the pancreatic parenchyma which may be focal, segmental, or diffuse.	2.31	1	0
Blood Poisoning [description not available]	2.42	2	0
Sepsis Systemic inflammatory response syndrome with a proven or suspected infectious etiology. When sepsis is associated with organ dysfunction distant from the site of infection, it is called severe sepsis. When sepsis is accompanied by HYPOTENSION despite adequate fluid infusion, it is called SEPTIC SHOCK.	2.42	2	0
Encephalopathy, Hepatic [description not available]	2.45	2	0
Hepatic Encephalopathy A syndrome characterized by central nervous system dysfunction in association with LIVER FAILURE, including portal-systemic shunts. Clinical features include lethargy and CONFUSION (frequently progressing to COMA); ASTERIXIS; NYSTAGMUS, PATHOLOGIC; brisk oculovestibular reflexes; decorticate and decerebrate posturing; MUSCLE SPASTICITY; and bilateral extensor plantar reflexes (see REFLEX, BABINSKI). ELECTROENCEPHALOGRAPHY may demonstrate triphasic waves. (From Adams et al., Principles of Neurology, 6th ed, pp1117-20; Plum & Posner, Diagnosis of Stupor and Coma, 3rd ed, p222-5)	2.45	2	0
Rheumatoid Arthritis [description not available]	2.25	1	0
Arthritis, Rheumatoid A chronic systemic disease, primarily of the joints, marked by inflammatory changes in the synovial membranes and articular structures, widespread fibrinoid degeneration of the collagen fibers in mesenchymal tissues, and by atrophy and rarefaction of bony structures. Etiology is unknown, but autoimmune mechanisms have been implicated.	2.25	1	0
B Virus Infection [description not available]	3.17	1	0
Cancer of Colon [description not available]	3.11	5	0
Colonic Neoplasms Tumors or cancer of the COLON.	3.11	5	0
Adjuvant Arthritis [description not available]	2.31	1	0
Colitis Gravis [description not available]	6.33	10	0
Colitis, Ulcerative Inflammation of the COLON that is predominantly confined to the MUCOSA. Its major symptoms include DIARRHEA, rectal BLEEDING, the passage of MUCUS, and ABDOMINAL PAIN.	6.33	10	0
MELAS [description not available]	2.31	1	0
Chronic Progressive External Ophthalmoplegia [description not available]	2.31	1	0
Electron Transport Chain Deficiencies, Mitochondrial [description not available]	4.26	6	0
MELAS Syndrome A mitochondrial disorder characterized by focal or generalized seizures, episodes of transient or persistent neurologic dysfunction resembling strokes, and ragged-red fibers on muscle biopsy. Affected individuals tend to be normal at birth through early childhood, then experience growth failure, episodic vomiting, and recurrent cerebral insults resulting in visual loss and hemiparesis. The cortical lesions tend to occur in the parietal and occipital lobes and are not associated with vascular occlusion. VASCULAR HEADACHE is frequently associated and the disorder tends to be familial. (From Joynt, Clinical Neurology, 1992, Ch56, p117)	2.31	1	0
Mitochondrial Diseases Diseases caused by abnormal function of the MITOCHONDRIA. They may be caused by mutations, acquired or inherited, in mitochondrial DNA or in nuclear genes that code for mitochondrial components. They may also be the result of acquired mitochondria dysfunction due to adverse effects of drugs, infections, or other environmental causes.	4.26	6	0
Infections, Helicobacter [description not available]	2.31	1	0
Helicobacter Infections Infections with organisms of the genus HELICOBACTER, particularly, in humans, HELICOBACTER PYLORI. The clinical manifestations are focused in the stomach, usually the gastric mucosa and antrum, and the upper duodenum. This infection plays a major role in the pathogenesis of type B gastritis and peptic ulcer disease.	2.31	1	0
Bladder Cancer [description not available]	2.73	3	0
Urinary Bladder Neoplasms Tumors or cancer of the URINARY BLADDER.	2.73	3	0
Campylobacter Infection [description not available]	2.15	1	0
Diabetic Glomerulosclerosis [description not available]	2.51	2	0
Diabetic Nephropathies KIDNEY injuries associated with diabetes mellitus and affecting KIDNEY GLOMERULUS; ARTERIOLES; KIDNEY TUBULES; and the interstitium. Clinical signs include persistent PROTEINURIA, from microalbuminuria progressing to ALBUMINURIA of greater than 300 mg/24 h, leading to reduced GLOMERULAR FILTRATION RATE and END-STAGE RENAL DISEASE.	2.51	2	0
Ataxia with Lactic Acidosis [description not available]	3.82	4	0
Pyruvate Dehydrogenase Complex Deficiency Disease An inherited metabolic disorder caused by deficient enzyme activity in the PYRUVATE DEHYDROGENASE COMPLEX, resulting in deficiency of acetyl CoA and reduced synthesis of acetylcholine. Two clinical forms are recognized: neonatal and juvenile. The neonatal form is a relatively common cause of lactic acidosis in the first weeks of life and may also feature an erythematous rash. The juvenile form presents with lactic acidosis, alopecia, intermittent ATAXIA; SEIZURES; and an erythematous rash. (From J Inherit Metab Dis 1996;19(4):452-62) Autosomal recessive and X-linked forms are caused by mutations in the genes for the three different enzyme components of this multisubunit pyruvate dehydrogenase complex. One of the mutations at Xp22.2-p22.1 in the gene for the E1 alpha component of the complex leads to LEIGH DISEASE.	3.82	4	0
Genome Instability [description not available]	2.8	3	0
B16 Melanoma [description not available]	2.15	1	0
Cardiac Toxicity [description not available]	2.15	1	0
Cardiac Diseases [description not available]	3.35	2	0
Heart Diseases Pathological conditions involving the HEART including its structural and functional abnormalities.	3.35	2	0
Cardiotoxicity Damage to the HEART or its function secondary to exposure to toxic substances such as drugs used in CHEMOTHERAPY; IMMUNOTHERAPY; or RADIATION.	2.15	1	0
Hepatoblastoma A malignant neoplasm occurring in young children, primarily in the liver, composed of tissue resembling embryonal or fetal hepatic epithelium, or mixed epithelial and mesenchymal tissues. (Stedman, 25th ed)	2.78	3	0
Hematologic Malignancies [description not available]	2.15	1	0
Androgen-Independent Prostatic Cancer [description not available]	2.15	1	0
Hematologic Neoplasms Neoplasms located in the blood and blood-forming tissue (the bone marrow and lymphatic tissue). The commonest forms are the various types of LEUKEMIA, of LYMPHOMA, and of the progressive, life-threatening forms of the MYELODYSPLASTIC SYNDROMES.	2.15	1	0
Prostatic Neoplasms, Castration-Resistant Tumors or cancer of the PROSTATE which can grow in the presence of low or residual amount of androgen hormones such as TESTOSTERONE.	2.15	1	0
Carcinoma, Anaplastic [description not available]	2.46	2	0
Cancer of Stomach [description not available]	2.15	1	0
Carcinoma A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.	2.46	2	0
Stomach Neoplasms Tumors or cancer of the STOMACH.	2.15	1	0
Diseases, Metabolic [description not available]	6.39	3	1
Metabolic Diseases Generic term for diseases caused by an abnormal metabolic process. It can be congenital due to inherited enzyme abnormality (METABOLISM, INBORN ERRORS) or acquired due to disease of an endocrine organ or failure of a metabolically important organ such as the liver. (Stedman, 26th ed)	6.39	3	1
Cerebral Infarction, Middle Cerebral Artery [description not available]	2.17	1	0
Apoplexy [description not available]	2.17	1	0
Cerebral Ischemia [description not available]	2.71	3	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.	2.71	3	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.	2.17	1	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)	2.17	1	0
Cancer of Prostate [description not available]	4.59	9	0
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	4.59	9	0
Disease Exacerbation [description not available]	3.96	4	0
Dyslipidemia [description not available]	2.17	1	0
Dyslipidemias Abnormalities in the serum levels of LIPIDS, including overproduction or deficiency. Abnormal serum lipid profiles may include high total CHOLESTEROL, high TRIGLYCERIDES, low HIGH DENSITY LIPOPROTEIN CHOLESTEROL, and elevated LOW DENSITY LIPOPROTEIN CHOLESTEROL.	2.17	1	0
Lymph Node Metastasis [description not available]	2.17	1	0
Atherogenesis [description not available]	2.17	1	0
Weight Gain Increase in BODY WEIGHT over existing weight.	2.81	3	0
Atherosclerosis A thickening and loss of elasticity of the walls of ARTERIES that occurs with formation of ATHEROSCLEROTIC PLAQUES within the ARTERIAL INTIMA.	2.17	1	0
Osteoarthritis of Knee [description not available]	2.17	1	0
Osteoarthritis, Knee Noninflammatory degenerative disease of the knee joint consisting of three large categories: conditions that block normal synchronous movement, conditions that produce abnormal pathways of motion, and conditions that cause stress concentration resulting in changes to articular cartilage. (Crenshaw, Campbell's Operative Orthopaedics, 8th ed, p2019)	2.17	1	0
Cell Transformation, Neoplastic Cell changes manifested by escape from control mechanisms, increased growth potential, alterations in the cell surface, karyotypic abnormalities, morphological and biochemical deviations from the norm, and other attributes conferring the ability to invade, metastasize, and kill.	2.5	2	0
Adamantiades-Behcet Disease [description not available]	2.17	1	0
Behcet Syndrome Rare chronic inflammatory disease involving the small blood vessels. It is of unknown etiology and characterized by mucocutaneous ulceration in the mouth and genital region and uveitis with hypopyon. The neuro-ocular form may cause blindness and death. SYNOVITIS; THROMBOPHLEBITIS; gastrointestinal ulcerations; RETINAL VASCULITIS; and OPTIC ATROPHY may occur as well.	2.17	1	0
Hutchinson Gilford Progeria Syndrome [description not available]	2.17	1	0
Progeria An abnormal congenital condition, associated with defects in the LAMIN TYPE A gene, which is characterized by premature aging in children, where all the changes of cell senescence occur. It is manifested by premature graying; hair loss; hearing loss (DEAFNESS); cataracts (CATARACT); ARTHRITIS; OSTEOPOROSIS; DIABETES MELLITUS; atrophy of subcutaneous fat; skeletal hypoplasia; elevated urinary HYALURONIC ACID; and accelerated ATHEROSCLEROSIS. Many affected individuals develop malignant tumors, especially SARCOMA.	2.17	1	0
Edema-Proteinuria-Hypertension Gestosis [description not available]	2.21	1	0
Pre-Eclampsia A complication of PREGNANCY, characterized by a complex of symptoms including maternal HYPERTENSION and PROTEINURIA with or without pathological EDEMA. Symptoms may range between mild and severe. Pre-eclampsia usually occurs after the 20th week of gestation, but may develop before this time in the presence of trophoblastic disease.	2.21	1	0
Carcinoma, Ductal, Pancreatic [description not available]	2.21	1	0
Carcinoma, Pancreatic Ductal Carcinoma that arises from the PANCREATIC DUCTS. It accounts for the majority of cancers derived from the PANCREAS.	2.21	1	0
Colitis, Granulomatous [description not available]	6.33	10	0
E coli Infections [description not available]	2.42	2	0
Crohn Disease A chronic transmural inflammation that may involve any part of the DIGESTIVE TRACT from MOUTH to ANUS, mostly found in the ILEUM, the CECUM, and the COLON. In Crohn disease, the inflammation, extending through the intestinal wall from the MUCOSA to the serosa, is characteristically asymmetric and segmental. Epithelioid GRANULOMAS may be seen in some patients.	6.33	10	0
Escherichia coli Infections Infections with bacteria of the species ESCHERICHIA COLI.	2.42	2	0
Adenoma, Basal Cell [description not available]	2.21	1	0
Cancer of Intestines [description not available]	2.21	1	0
Adenomatous Polyposis Coli, Familial [description not available]	2.21	1	0
Adenoma A benign epithelial tumor with a glandular organization.	2.21	1	0
Intestinal Neoplasms Tumors or cancer of the INTESTINES.	2.21	1	0
Adenomatous Polyposis Coli A polyposis syndrome due to an autosomal dominant mutation of the APC genes (GENES, APC) on CHROMOSOME 5. The syndrome is characterized by the development of hundreds of ADENOMATOUS POLYPS in the COLON and RECTUM of affected individuals by early adulthood.	2.21	1	0
Diffuse Large B-Cell Lymphoma [description not available]	3.43	2	0
Lymphoma, Large B-Cell, Diffuse Malignant lymphoma composed of large B lymphoid cells whose nuclear size can exceed normal macrophage nuclei, or more than twice the size of a normal lymphocyte. The pattern is predominantly diffuse. Most of these lymphomas represent the malignant counterpart of B-lymphocytes at midstage in the process of differentiation.	3.43	2	0
Invasiveness, Neoplasm [description not available]	4.24	3	0
Affective Psychosis, Bipolar [description not available]	2.48	2	0
Aura [description not available]	2.21	1	0
Bipolar Disorder A major affective disorder marked by severe mood swings (manic or major depressive episodes) and a tendency to remission and recurrence.	2.48	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)	2.21	1	0
Leucocythaemia [description not available]	2.08	1	0
Leukemia A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)	2.08	1	0
Moniliasis, Oral [description not available]	2.08	1	0
Carcinoma, Epidermoid [description not available]	2.49	2	0
Cancer of Mouth [description not available]	2.08	1	0
AIRE Deficiency [description not available]	2.08	1	0
Candidiasis, Chronic Mucocutaneous A clinical syndrome characterized by development, usually in infancy or childhood, of a chronic, often widespread candidiasis of skin, nails, and mucous membranes. It may be secondary to one of the immunodeficiency syndromes, inherited as an autosomal recessive trait, or associated with defects in cell-mediated immunity, endocrine disorders, dental stomatitis, or malignancy.	2.08	1	0
Candidiasis, Oral Infection of the mucous membranes of the mouth by a fungus of the genus CANDIDA. (Dorland, 27th ed)	2.08	1	0
Carcinoma, Squamous Cell A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed)	2.49	2	0
Mouth Neoplasms Tumors or cancer of the MOUTH.	2.08	1	0
Neuroblastoma A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)	4.17	16	0
Lethargy A general state of sluggishness, listless, or uninterested, with being tired, and having difficulty concentrating and doing simple tasks. It may be related to DEPRESSION or DRUG ADDICTION.	2.08	1	0
Fasting Hypoglycemia HYPOGLYCEMIA expressed in the postabsorptive state, after prolonged FASTING, or an overnight fast.	4.27	4	0
Hypoglycemia A syndrome of abnormally low BLOOD GLUCOSE level. Clinical hypoglycemia has diverse etiologies. Severe hypoglycemia eventually lead to glucose deprivation of the CENTRAL NERVOUS SYSTEM resulting in HUNGER; SWEATING; PARESTHESIA; impaired mental function; SEIZURES; COMA; and even DEATH.	4.27	4	0
Diabetes Mellitus A heterogeneous group of disorders characterized by HYPERGLYCEMIA and GLUCOSE INTOLERANCE.	8.88	19	0
7-Dehydrocholesterol Reductase Deficiency [description not available]	3.38	2	0
Chorea Disorders [description not available]	3.01	1	0
Autosomal Dominant Hereditary Spastic Paraplegia [description not available]	3.01	1	0
Chorea Involuntary, forcible, rapid, jerky movements that may be subtle or become confluent, markedly altering normal patterns of movement. Hypotonia and pendular reflexes are often associated. Conditions which feature recurrent or persistent episodes of chorea as a primary manifestation of disease are referred to as CHOREATIC DISORDERS. Chorea is also a frequent manifestation of BASAL GANGLIA DISEASES.	3.01	1	0
Optic Atrophy Atrophy of the optic disk which may be congenital or acquired. This condition indicates a deficiency in the number of nerve fibers which arise in the RETINA and converge to form the OPTIC DISK; OPTIC NERVE; OPTIC CHIASM; and optic tracts. GLAUCOMA; ISCHEMIA; inflammation, a chronic elevation of intracranial pressure, toxins, optic nerve compression, and inherited conditions (see OPTIC ATROPHIES, HEREDITARY) are relatively common causes of this condition.	3.01	1	0
Spastic Paraplegia, Hereditary A group of inherited diseases that share similar phenotypes but are genetically diverse. Different genetic loci for autosomal recessive, autosomal dominant, and x-linked forms of hereditary spastic paraplegia have been identified. Clinically, patients present with slowly progressive distal limb weakness and lower extremity spasticity. Peripheral sensory neurons may be affected in the later stages of the disease. (J Neurol Neurosurg Psychiatry 1998 Jan;64(1):61-6; Curr Opin Neurol 1997 Aug;10(4):313-8)	3.01	1	0
Smith-Lemli-Opitz Syndrome An autosomal recessive disorder of CHOLESTEROL metabolism. It is caused by a deficiency of 7-dehydrocholesterol reductase, the enzyme that converts 7-dehydrocholesterol to cholesterol, leading to an abnormally low plasma cholesterol. This syndrome is characterized by multiple CONGENITAL ABNORMALITIES, growth deficiency, and INTELLECTUAL DISABILITY.	3.38	2	0
Injury, Ischemia-Reperfusion [description not available]	2.42	2	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.	2.42	2	0
Adenocarcinoma, Basal Cell [description not available]	3.11	5	0
Carcinoma, Intraepithelial [description not available]	2.1	1	0
Carcinoma, Non-Small Cell Lung [description not available]	3.4	2	0
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	3.11	5	0
Carcinoma in Situ A lesion with cytological characteristics associated with invasive carcinoma but the tumor cells are confined to the epithelium of origin, without invasion of the basement membrane.	2.1	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.	3.4	2	0
Infection [description not available]	2.41	2	0
Nerve Degeneration Loss of functional activity and trophic degeneration of nerve axons and their terminal arborizations following the destruction of their cells of origin or interruption of their continuity with these cells. The pathology is characteristic of neurodegenerative diseases. Often the process of nerve degeneration is studied in research on neuroanatomical localization and correlation of the neurophysiology of neural pathways.	2.94	4	0
Infections Invasion of the host organism by microorganisms or their toxins or by parasites that can cause pathological conditions or diseases.	2.41	2	0
Chronic Primary Open Angle Glaucoma [description not available]	2.1	1	0
Glaucoma An ocular disease, occurring in many forms, having as its primary characteristics an unstable or a sustained increase in the intraocular pressure which the eye cannot withstand without damage to its structure or impairment of its function. The consequences of the increased pressure may be manifested in a variety of symptoms, depending upon type and severity, such as excavation of the optic disk, hardness of the eyeball, corneal anesthesia, reduced visual acuity, seeing of colored halos around lights, disturbed dark adaptation, visual field defects, and headaches. (Dictionary of Visual Science, 4th ed)	2.1	1	0
Glaucoma, Open-Angle Glaucoma in which the angle of the anterior chamber is open and the trabecular meshwork does not encroach on the base of the iris.	2.1	1	0
Intraocular Pressure The pressure of the fluids in the eye.	2.1	1	0
Diabetic Angiopathies VASCULAR DISEASES that are associated with DIABETES MELLITUS.	2.1	1	0
Acidosis, Diabetic [description not available]	4.14	6	0
Diabetic Ketoacidosis A life-threatening complication of diabetes mellitus, primarily of TYPE 1 DIABETES MELLITUS with severe INSULIN deficiency and extreme HYPERGLYCEMIA. It is characterized by KETOSIS; DEHYDRATION; and depressed consciousness leading to COMA.	4.14	6	0
Diabetic Coma A state of unconsciousness as a complication of diabetes mellitus. It occurs in cases of extreme HYPERGLYCEMIA or extreme HYPOGLYCEMIA as a complication of INSULIN therapy.	3.01	1	0
Cancer of Skin [description not available]	3.4	2	0
Skin Neoplasms Tumors or cancer of the SKIN.	3.4	2	0
Infections, Salmonella [description not available]	2.1	1	0
Anoxia-Ischemia, Brain [description not available]	2.52	2	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.	2.52	2	0
Cold Panniculitis [description not available]	2.52	2	0
Autoimmune Diabetes [description not available]	4.05	5	0
Diabetes Mellitus, Type 1 A subtype of DIABETES MELLITUS that is characterized by INSULIN deficiency. It is manifested by the sudden onset of severe HYPERGLYCEMIA, rapid progression to DIABETIC KETOACIDOSIS, and DEATH unless treated with insulin. The disease may occur at any age, but is most common in childhood or adolescence.	4.05	5	0
Infection, Toxoplasma gondii [description not available]	2.11	1	0
Toxoplasmosis The acquired form of infection by Toxoplasma gondii in animals and man.	2.11	1	0
Delayed Effects, Prenatal Exposure [description not available]	2.46	2	0
Cancer of Ovary [description not available]	2.69	3	0
Ovarian Neoplasms Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.	2.69	3	0
Inborn Urea Cycle Disorder [description not available]	2.13	1	0
Urea Cycle Disorders, Inborn Rare congenital metabolism disorders of the urea cycle. The disorders are due to mutations that result in complete (neonatal onset) or partial (childhood or adult onset) inactivity of an enzyme, involved in the urea cycle. Neonatal onset results in clinical features that include irritability, vomiting, lethargy, seizures, NEONATAL HYPOTONIA; RESPIRATORY ALKALOSIS; HYPERAMMONEMIA; coma, and death. Survivors of the neonatal onset and childhood/adult onset disorders share common risks for ENCEPHALOPATHIES, METABOLIC, INBORN; and RESPIRATORY ALKALOSIS due to HYPERAMMONEMIA.	2.13	1	0
Dementia Praecox [description not available]	2.13	1	0
Schizophrenia A severe emotional disorder of psychotic depth characteristically marked by a retreat from reality with delusion formation, HALLUCINATIONS, emotional disharmony, and regressive behavior.	2.13	1	0
Infections, Retroviridae [description not available]	2.15	1	0
Fibroma, Shope [description not available]	2.15	1	0
Experimental Mammary Neoplasms [description not available]	3.8	4	0
Retroviridae Infections Virus diseases caused by the RETROVIRIDAE.	2.15	1	0
Cytomegalic Inclusion Disease [description not available]	2.15	1	0
Cytomegalovirus Infections Infection with CYTOMEGALOVIRUS, characterized by enlarged cells bearing intranuclear inclusions. Infection may be in almost any organ, but the salivary glands are the most common site in children, as are the lungs in adults.	2.15	1	0
Cytomegalovirus A genus of the family HERPESVIRIDAE, subfamily BETAHERPESVIRINAE, infecting the salivary glands, liver, spleen, lungs, eyes, and other organs, in which they produce characteristically enlarged cells with intranuclear inclusions. Infection with Cytomegalovirus is also seen as an opportunistic infection in AIDS.	2.15	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
Leukemia, Lymphoblastic, Acute, T Cell [description not available]	2.05	1	0
Leukemia, Pre-B-Cell [description not available]	2.05	1	0
Precursor B-Cell Lymphoblastic Leukemia-Lymphoma A leukemia/lymphoma found predominately in children and adolescents and characterized by a high number of lymphoblasts and solid tumor lesions. Frequent sites involve LYMPH NODES, skin, and bones. It most commonly presents as leukemia.	2.05	1	0
Precursor T-Cell Lymphoblastic Leukemia-Lymphoma A leukemia/lymphoma found predominately in children and young adults and characterized LYMPHADENOPATHY and THYMUS GLAND involvement. It most frequently presents as a lymphoma, but a leukemic progression in the bone marrow is common.	2.05	1	0
Candida Infection [description not available]	2.44	2	0
Candidiasis Infection with a fungus of the genus CANDIDA. It is usually a superficial infection of the moist areas of the body and is generally caused by CANDIDA ALBICANS. (Dorland, 27th ed)	2.44	2	0
Heart Disease, Ischemic [description not available]	4.77	7	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).	4.77	7	0
Kahler Disease [description not available]	2.05	1	0
Multiple Myeloma A malignancy of mature PLASMA CELLS engaging in monoclonal immunoglobulin production. It is characterized by hyperglobulinemia, excess Bence-Jones proteins (free monoclonal IMMUNOGLOBULIN LIGHT CHAINS) in the urine, skeletal destruction, bone pain, and fractures. Other features include ANEMIA; HYPERCALCEMIA; and RENAL INSUFFICIENCY.	2.05	1	0
Lead Poisoning, Nervous System Injury to the nervous system secondary to exposure to lead compounds. Two distinct clinical patterns occur in children (LEAD POISONING, NERVOUS SYSTEM, CHILDHOOD) and adults (LEAD POISONING, NERVOUS SYSTEM, ADULT). In children, lead poisoning typically produces an encephalopathy. In adults, exposure to toxic levels of lead is associated with a peripheral neuropathy.	2.04	1	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)	3.5	8	0
Injury, Myocardial Reperfusion [description not available]	2.76	3	0
Deficiency, Glucosephosphatase [description not available]	2.05	1	0
Glycogen Storage Disease Type I An autosomal recessive disease in which gene expression of glucose-6-phosphatase is absent, resulting in hypoglycemia due to lack of glucose production. Accumulation of glycogen in liver and kidney leads to organomegaly, particularly massive hepatomegaly. Increased concentrations of lactic acid and hyperlipidemia appear in the plasma. Clinical gout often appears in early childhood.	2.05	1	0
Diabetic Retinopathy Disease of the RETINA as a complication of DIABETES MELLITUS. It is characterized by the progressive microvascular complications, such as ANEURYSM, interretinal EDEMA, and intraocular PATHOLOGIC NEOVASCULARIZATION.	2.05	1	0
Experimental Hepatoma [description not available]	4.05	3	0
Cardiomyopathies, Primary [description not available]	2.94	4	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).	2.94	4	0
Alcoholic Hepatitis [description not available]	2.05	1	0
Hepatitis, Alcoholic INFLAMMATION of the LIVER due to ALCOHOL ABUSE. It is characterized by NECROSIS of HEPATOCYTES, infiltration by NEUTROPHILS, and deposit of MALLORY BODIES. Depending on its severity, the inflammatory lesion may be reversible or progress to LIVER CIRRHOSIS.	2.05	1	0
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	6.42	11	0
Beriberi, Cerebral [description not available]	2.05	1	0
Dental Plaque A film that attaches to teeth, often causing DENTAL CARIES and GINGIVITIS. It is composed of MUCINS, secreted from salivary glands, and microorganisms.	2.05	1	0
Ovine Diseases [description not available]	2.06	1	0
Trichostrongyloidiasis Infection by roundworms of the superfamily TRICHOSTRONGYLOIDEA, including the genera TRICHOSTRONGYLUS; OSTERTAGIA; Cooperia, HAEMONCHUS; Nematodirus, Hyostrongylus, and DICTYOCAULUS.	2.06	1	0
Recrudescence [description not available]	3.38	2	0
Brill-Symmers Disease [description not available]	2.98	1	0
B-Cell Lymphoma [description not available]	2.98	1	0
Lymphoma, Follicular Malignant lymphoma in which the lymphomatous cells are clustered into identifiable nodules within the LYMPH NODES. The nodules resemble to some extent the GERMINAL CENTER of lymph node follicles and most likely represent neoplastic proliferation of lymph node-derived follicular center B-LYMPHOCYTES.	2.98	1	0
Lymphoma, B-Cell A group of heterogeneous lymphoid tumors generally expressing one or more B-cell antigens or representing malignant transformations of B-lymphocytes.	2.98	1	0
Cystic Fibrosis of Pancreas [description not available]	2.06	1	0
Cystic Fibrosis An autosomal recessive genetic disease of the EXOCRINE GLANDS. It is caused by mutations in the gene encoding the CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR expressed in several organs including the LUNG, the PANCREAS, the BILIARY SYSTEM, and the SWEAT GLANDS. Cystic fibrosis is characterized by epithelial secretory dysfunction associated with ductal obstruction resulting in AIRWAY OBSTRUCTION; chronic RESPIRATORY INFECTIONS; PANCREATIC INSUFFICIENCY; maldigestion; salt depletion; and HEAT PROSTRATION.	2.06	1	0
Bacillus anthracis Infection [description not available]	2.06	1	0
Anthrax An acute infection caused by the spore-forming bacteria BACILLUS ANTHRACIS. It commonly affects hoofed animals such as sheep and goats. Infection in humans often involves the skin (cutaneous anthrax), the lungs (inhalation anthrax), or the gastrointestinal tract. Anthrax is not contagious and can be treated with antibiotics.	2.06	1	0
Pulmonary Consumption [description not available]	2.06	1	0
Tuberculosis, Pulmonary MYCOBACTERIUM infections of the lung.	2.06	1	0
Hibernation, Myocardial [description not available]	2.06	1	0
Coronary Artery Stenosis [description not available]	2.06	1	0
Coronary Stenosis Narrowing or constriction of a coronary artery.	2.06	1	0
Atypical Mycobacterial Infection, Disseminated [description not available]	2.06	1	0
Cancer of the Uterus [description not available]	2.06	1	0
Leiomyomatosis The state of having multiple leiomyomas throughout the body. (Stedman, 25th ed)	2.06	1	0
Cancer Syndromes, Hereditary [description not available]	2.06	1	0
Uterine Neoplasms Tumors or cancer of the UTERUS.	2.06	1	0
Primary Graft Dysfunction A form of ischemia-reperfusion injury occurring in the early period following transplantation. Significant pathophysiological changes in MITOCHONDRIA are the main cause of the dysfunction. It is most often seen in the transplanted lung, liver, or kidney and can lead to GRAFT REJECTION.	2.07	1	0
Proteinuria The presence of proteins in the urine, an indicator of KIDNEY DISEASES.	2.38	2	0
Adenocarcinoma Of Kidney [description not available]	3.38	2	0
Carcinoma, Renal Cell A heterogeneous group of sporadic or hereditary carcinoma derived from cells of the KIDNEYS. There are several subtypes including the clear cells, the papillary, the chromophobe, the collecting duct, the spindle cells (sarcomatoid), or mixed cell-type carcinoma.	3.38	2	0
Diabetic Cardiomyopathies Diabetes complications in which VENTRICULAR REMODELING in the absence of CORONARY ATHEROSCLEROSIS and hypertension results in cardiac dysfunctions, typically LEFT VENTRICULAR DYSFUNCTION. The changes also result in myocardial hypertrophy, myocardial necrosis and fibrosis, and collagen deposition due to impaired glucose tolerance.	2.99	1	0
Cardiac Hypertrophy Enlargement of the HEART due to chamber HYPERTROPHY, an increase in wall thickness without an increase in the number of cells (MYOCYTES, CARDIAC). It is the result of increase in myocyte size, mitochondrial and myofibrillar mass, as well as changes in extracellular matrix.	6.5	12	0
Cardiomegaly Enlargement of the HEART, usually indicated by a cardiothoracic ratio above 0.50. Heart enlargement may involve the right, the left, or both HEART VENTRICLES or HEART ATRIA. Cardiomegaly is a nonspecific symptom seen in patients with chronic systolic heart failure (HEART FAILURE) or several forms of CARDIOMYOPATHIES.	6.5	12	0
Absence Seizure [description not available]	9.03	37	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.	9.03	37	0
C gattii Infection [description not available]	2.07	1	0
Cryptococcosis Fungal infection caused by genus CRYPTOCOCCUS.	2.07	1	0
Extravascular Hemolysis [description not available]	2.07	1	0
Hemolysis The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.	2.07	1	0
Muscle Relaxation That phase of a muscle twitch during which a muscle returns to a resting position.	2.08	1	0
Left Ventricular Hypertrophy [description not available]	2.08	1	0
Blood Pressure, High [description not available]	3.6	3	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.	3.6	3	0
Hypertrophy, Left Ventricular Enlargement of the LEFT VENTRICLE of the heart. This increase in ventricular mass is attributed to sustained abnormal pressure or volume loads and is a contributor to cardiovascular morbidity and mortality.	2.08	1	0
Muscle Contraction A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.	5.8	8	0
Basophilic Leukemia, Acute [description not available]	2.01	1	0
Leukemia, Basophilic, Acute A rare acute myeloid leukemia in which the primary differentiation is to BASOPHILS. It is characterized by an extreme increase of immature basophilic granulated cells in the bone marrow and blood. Mature basophils are usually sparse.	2.01	1	0
Manganese Poisoning Manganese poisoning is associated with chronic inhalation of manganese particles by individuals who work with manganese ore. Clinical features include CONFUSION; HALLUCINATIONS; and an extrapyramidal syndrome (PARKINSON DISEASE, SECONDARY) that includes rigidity; DYSTONIA; retropulsion; and TREMOR. (Adams, Principles of Neurology, 6th ed, p1213)	2.01	1	0
Cryptosporidium Infection [description not available]	2.01	1	0
Canine Diseases [description not available]	2.01	1	0
Cholera Infantum [description not available]	2.01	1	0
Cryptosporidiosis Intestinal infection with organisms of the genus CRYPTOSPORIDIUM. It occurs in both animals and humans. Symptoms include severe DIARRHEA.	2.01	1	0
Adrenoleukodystrophy, Autosomal Neonatal Form [description not available]	2.93	1	0
Peroxisomal Disorders A heterogeneous group of inherited metabolic disorders marked by absent or dysfunctional PEROXISOMES. Peroxisomal enzymatic abnormalities may be single or multiple. Biosynthetic peroxisomal pathways are compromised, including the ability to synthesize ether lipids and to oxidize long-chain fatty acid precursors. Diseases in this category include ZELLWEGER SYNDROME; INFANTILE REFSUM DISEASE; rhizomelic chondrodysplasia (CHONDRODYSPLASIA PUNCTATA, RHIZOMELIC); hyperpipecolic acidemia; neonatal adrenoleukodystrophy; and ADRENOLEUKODYSTROPHY (X-linked). Neurologic dysfunction is a prominent feature of most peroxisomal disorders.	2.93	1	0
Diseases, Peripheral Vascular [description not available]	3.85	1	0
Peripheral Vascular Diseases Pathological processes involving any one of the BLOOD VESSELS in the vasculature outside the HEART.	3.85	1	0
Compensatory Hyperinsulinemia A GLUCOSE-induced HYPERINSULINEMIA, a marker of insulin-resistant state. It is a mechanism to compensate for reduced sensitivity to insulin.	3.59	3	0
Hyperinsulinism A syndrome with excessively high INSULIN levels in the BLOOD. It may cause HYPOGLYCEMIA. Etiology of hyperinsulinism varies, including hypersecretion of a beta cell tumor (INSULINOMA); autoantibodies against insulin (INSULIN ANTIBODIES); defective insulin receptor (INSULIN RESISTANCE); or overuse of exogenous insulin or HYPOGLYCEMIC AGENTS.	3.59	3	0
Abnormalities, Multiple Congenital abnormalities that affect more than one organ or body structure.	2.94	1	0
Amino Acid Metabolism Disorders, Inborn [description not available]	3.99	5	0
Adenoma, Prostatic [description not available]	2.42	2	0
Prostatic Hyperplasia Increase in constituent cells in the PROSTATE, leading to enlargement of the organ (hypertrophy) and adverse impact on the lower urinary tract function. This can be caused by increased rate of cell proliferation, reduced rate of cell death, or both.	7.42	2	0
Hyperuricemia Excessive URIC ACID or urate in blood as defined by its solubility in plasma at 37 degrees C; greater than 0.42mmol per liter (7.0mg/dL) in men or 0.36mmol per liter (6.0mg/dL) in women. This condition is caused by overproduction of uric acid or impaired renal clearance. Hyperuricemia can be acquired, drug-induced or genetically determined (LESCH-NYHAN SYNDROME). It is associated with HYPERTENSION and GOUT.	2.94	1	0
Bleeding [description not available]	2.03	1	0
Fatty Liver with Encephalopathy [description not available]	3.31	2	0
Hemorrhage Bleeding or escape of blood from a vessel.	2.03	1	0
Acetyl-CoA:alpha-Glucosaminide N-Acetyltransferase Deficiency [description not available]	2.39	2	0
Mucopolysaccharidosis III Mucopolysaccharidosis characterized by heparitin sulfate in the urine, progressive mental retardation, mild dwarfism, and other skeletal disorders. There are four clinically indistinguishable but biochemically distinct forms, each due to a deficiency of a different enzyme.	2.39	2	0
ANS (Autonomic Nervous System) Diseases [description not available]	2.03	1	0
Amentia [description not available]	1.95	1	0
Dementia An acquired organic mental disorder with loss of intellectual abilities of sufficient severity to interfere with social or occupational functioning. The dysfunction is multifaceted and involves memory, behavior, personality, judgment, attention, spatial relations, language, abstract thought, and other executive functions. The intellectual decline is usually progressive, and initially spares the level of consciousness.	1.95	1	0
BH4 Deficiency [description not available]	2.65	3	0
Phenylketonurias A group of autosomal recessive disorders marked by a deficiency of the hepatic enzyme PHENYLALANINE HYDROXYLASE or less frequently by reduced activity of DIHYDROPTERIDINE REDUCTASE (i.e., atypical phenylketonuria). Classical phenylketonuria is caused by a severe deficiency of phenylalanine hydroxylase and presents in infancy with developmental delay; SEIZURES; skin HYPOPIGMENTATION; ECZEMA; and demyelination in the central nervous system. (From Adams et al., Principles of Neurology, 6th ed, p952).	2.65	3	0
Experimental Neoplasms [description not available]	3.34	7	0
Mucopolysaccharidosis [description not available]	2.36	2	0
Mucopolysaccharidoses Group of lysosomal storage diseases each caused by an inherited deficiency of an enzyme involved in the degradation of glycosaminoglycans (mucopolysaccharides). The diseases are progressive and often display a wide spectrum of clinical severity within one enzyme deficiency.	2.36	2	0
Bilharziasis [description not available]	1.96	1	0
Schistosomiasis Infection with flukes (trematodes) of the genus SCHISTOSOMA. Three species produce the most frequent clinical diseases: SCHISTOSOMA HAEMATOBIUM (endemic in Africa and the Middle East), SCHISTOSOMA MANSONI (in Egypt, northern and southern Africa, some West Indies islands, northern 2/3 of South America), and SCHISTOSOMA JAPONICUM (in Japan, China, the Philippines, Celebes, Thailand, Laos). S. mansoni is often seen in Puerto Ricans living in the United States.	1.96	1	0
Alcohol Abuse [description not available]	3.28	2	0
Alcoholism A primary, chronic disease with genetic, psychosocial, and environmental factors influencing its development and manifestations. The disease is often progressive and fatal. It is characterized by impaired control over drinking, preoccupation with the drug alcohol, use of alcohol despite adverse consequences, and distortions in thinking, most notably denial. Each of these symptoms may be continuous or periodic. (Morse & Flavin for the Joint Commission of the National Council on Alcoholism and Drug Dependence and the American Society of Addiction Medicine to Study the Definition and Criteria for the Diagnosis of Alcoholism: in JAMA 1992;268:1012-4)	3.28	2	0
Hyperthyroid [description not available]	2.87	4	0
Hyperthyroidism Hypersecretion of THYROID HORMONES from the THYROID GLAND. Elevated levels of thyroid hormones increase BASAL METABOLIC RATE.	2.87	4	0
Acidosis, Respiratory Respiratory retention of carbon dioxide. It may be chronic or acute.	2.87	1	0
Ataxia Impairment of the ability to perform smoothly coordinated voluntary movements. This condition may affect the limbs, trunk, eyes, pharynx, larynx, and other structures. Ataxia may result from impaired sensory or motor function. Sensory ataxia may result from posterior column injury or PERIPHERAL NERVE DISEASES. Motor ataxia may be associated with CEREBELLAR DISEASES; CEREBRAL CORTEX diseases; THALAMIC DISEASES; BASAL GANGLIA DISEASES; injury to the RED NUCLEUS; and other conditions.	3.34	1	1
Cerebellar Diseases Diseases that affect the structure or function of the cerebellum. Cardinal manifestations of cerebellar dysfunction include dysmetria, GAIT ATAXIA, and MUSCLE HYPOTONIA.	3.34	1	1
Spider Veins [description not available]	3.34	1	1
Atrophy Decrease in the size of a cell, tissue, organ, or multiple organs, associated with a variety of pathological conditions such as abnormal cellular changes, ischemia, malnutrition, or hormonal changes.	3.34	1	1
Telangiectasis Permanent dilation of preexisting blood vessels (CAPILLARIES; ARTERIOLES; VENULES) creating small focal red lesions, most commonly in the skin or mucous membranes. It is characterized by the prominence of skin blood vessels, such as vascular spiders.	3.34	1	1
Deficiency, Protein [description not available]	2.87	1	0
Bovine Diseases [description not available]	2.87	1	0
Adult Fanconi Syndrome [description not available]	1.96	1	0
Sarcoma 180 An experimental sarcoma of mice.	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.	2.36	2	0
Carbon Tetrachloride Poisoning Poisoning that results from ingestion, injection, inhalation, or skin absorption of CARBON TETRACHLORIDE.	1.95	1	0
Adipocere [description not available]	1.95	1	0
Arsenic Encephalopathy [description not available]	1.98	1	0
Lipid Metabolism, Inborn Error [description not available]	3.78	2	0
Vascular Diseases Pathological processes involving any of the BLOOD VESSELS in the cardiac or peripheral circulation. They include diseases of ARTERIES; VEINS; and rest of the vasculature system in the body.	2.9	1	0
Deficiency Disease, Ornithine Carbamoyltransferase [description not available]	2.39	2	0
Ornithine Carbamoyltransferase Deficiency Disease An inherited urea cycle disorder associated with deficiency of the enzyme ORNITHINE CARBAMOYLTRANSFERASE, transmitted as an X-linked trait and featuring elevations of amino acids and ammonia in the serum. Clinical features, which are more prominent in males, include seizures, behavioral alterations, episodic vomiting, lethargy, and coma. (Menkes, Textbook of Child Neurology, 5th ed, pp49-50)	2.39	2	0
Lactic Acidosis [description not available]	2.38	2	0
Beriberi A disease caused by a deficiency of thiamine (vitamin B1) and characterized by polyneuritis, cardiac pathology, and edema. The epidemic form is found primarily in areas in which white (polished) rice is the staple food, as in Japan, China, the Philippines, India, and other countries of southeast Asia. (Dorland, 27th ed)	1.98	1	0
Acidosis, Lactic Acidosis caused by accumulation of lactic acid more rapidly than it can be metabolized. It may occur spontaneously or in association with diseases such as DIABETES MELLITUS; LEUKEMIA; or LIVER FAILURE.	2.38	2	0
Chronic Illness [description not available]	2.65	3	0
Chronic Disease Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).	2.65	3	0
Arrhythmia [description not available]	2.9	1	0
Coronary Heart Disease [description not available]	3.8	4	0
Arrhythmias, Cardiac Any disturbances of the normal rhythmic beating of the heart or MYOCARDIAL CONTRACTION. Cardiac arrhythmias can be classified by the abnormalities in HEART RATE, disorders of electrical impulse generation, or impulse conduction.	2.9	1	0
Coronary Disease An imbalance between myocardial functional requirements and the capacity of the CORONARY VESSELS to supply sufficient blood flow. It is a form of MYOCARDIAL ISCHEMIA (insufficient blood supply to the heart muscle) caused by a decreased capacity of the coronary vessels.	3.8	4	0
Brain Disorders [description not available]	4.39	3	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.	4.39	3	0
Addison Disease and Cerebral Sclerosis [description not available]	2.9	1	0
Adrenoleukodystrophy An X-linked recessive disorder characterized by the accumulation of saturated very long chain fatty acids in the LYSOSOMES of ADRENAL CORTEX and the white matter of CENTRAL NERVOUS SYSTEM. This disease occurs almost exclusively in the males. Clinical features include the childhood onset of ATAXIA; NEUROBEHAVIORAL MANIFESTATIONS; HYPERPIGMENTATION; ADRENAL INSUFFICIENCY; SEIZURES; MUSCLE SPASTICITY; and DEMENTIA. The slowly progressive adult form is called adrenomyeloneuropathy. The defective gene ABCD1 is located at Xq28, and encodes the adrenoleukodystrophy protein (ATP-BINDING CASSETTE TRANSPORTERS).	2.9	1	0
Anesthesia A state characterized by loss of feeling or sensation. This depression of nerve function is usually the result of pharmacologic action and is induced to allow performance of surgery or other painful procedures.	1.99	1	0
Nephrotic Syndrome A condition characterized by severe PROTEINURIA, greater than 3.5 g/day in an average adult. The substantial loss of protein in the urine results in complications such as HYPOPROTEINEMIA; generalized EDEMA; HYPERTENSION; and HYPERLIPIDEMIAS. Diseases associated with nephrotic syndrome generally cause chronic kidney dysfunction.	2.37	2	0
Di Guglielmo Disease [description not available]	1.99	1	0
Leukemia, Erythroblastic, Acute A myeloproliferative disorder characterized by neoplastic proliferation of erythroblastic and myeloblastic elements with atypical erythroblasts and myeloblasts in the peripheral blood.	1.99	1	0
Granulocytic Leukemia, Chronic [description not available]	1.99	1	0
Leukemia, Myelogenous, Chronic, BCR-ABL Positive Clonal hematopoetic disorder caused by an acquired genetic defect in PLURIPOTENT STEM CELLS. It starts in MYELOID CELLS of the bone marrow, invades the blood and then other organs. The condition progresses from a stable, more indolent, chronic phase (LEUKEMIA, MYELOID, CHRONIC PHASE) lasting up to 7 years, to an advanced phase composed of an accelerated phase (LEUKEMIA, MYELOID, ACCELERATED PHASE) and BLAST CRISIS.	1.99	1	0
Gastroduodenal Ulcer [description not available]	1.99	1	0
Peptic Ulcer Ulcer that occurs in the regions of the GASTROINTESTINAL TRACT which come into contact with GASTRIC JUICE containing PEPSIN and GASTRIC ACID. It occurs when there are defects in the MUCOSA barrier. The common forms of peptic ulcers are associated with HELICOBACTER PYLORI and the consumption of nonsteroidal anti-inflammatory drugs (NSAIDS).	1.99	1	0
Asymmetric Diabetic Proximal Motor Neuropathy [description not available]	2.91	1	0
Diabetic Neuropathies Peripheral, autonomic, and cranial nerve disorders that are associated with DIABETES MELLITUS. These conditions usually result from diabetic microvascular injury involving small blood vessels that supply nerves (VASA NERVORUM). Relatively common conditions which may be associated with diabetic neuropathy include third nerve palsy (see OCULOMOTOR NERVE DISEASES); MONONEUROPATHY; mononeuropathy multiplex; diabetic amyotrophy; a painful POLYNEUROPATHY; autonomic neuropathy; and thoracoabdominal neuropathy. (From Adams et al., Principles of Neurology, 6th ed, p1325)	2.91	1	0
Encephalopathy, Toxic [description not available]	2.92	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.	2.92	1	0
Hemorrhagic Shock [description not available]	2	1	0
Embryopathies [description not available]	2.92	1	0
Complications, Pregnancy [description not available]	2.92	1	0
Cot Death [description not available]	3.77	2	0
Colitis Inflammation of the COLON section of the large intestine (INTESTINE, LARGE), usually with symptoms such as DIARRHEA (often with blood and mucus), ABDOMINAL PAIN, and FEVER.	2	1	0
Cancer of Nose [description not available]	2	1	0
Hyperoxia An abnormal increase in the amount of oxygen in the tissues and organs.	3.39	1	1
Alveolar Echinococcosis, Hepatic [description not available]	2.01	1	0
Choline Deficiency A condition produced by a deficiency of CHOLINE in animals. Choline is known as a lipotropic agent because it has been shown to promote the transport of excess fat from the liver under certain conditions in laboratory animals. Combined deficiency of choline (included in the B vitamin complex) and all other methyl group donors causes liver cirrhosis in some animals. Unlike compounds normally considered as vitamins, choline does not serve as a cofactor in enzymatic reactions. (From Saunders Dictionary & Encyclopedia of Laboratory Medicine and Technology, 1984)	2.87	1	0
Ache [description not available]	2.87	1	0
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	2.87	1	0
Anoxia, Brain [description not available]	1.95	1	0
Adult Refsum Disease [description not available]	2.86	1	0
Central Hypothyroidism [description not available]	1.95	1	0
Hypothyroidism A syndrome that results from abnormally low secretion of THYROID HORMONES from the THYROID GLAND, leading to a decrease in BASAL METABOLIC RATE. In its most severe form, there is accumulation of MUCOPOLYSACCHARIDES in the SKIN and EDEMA, known as MYXEDEMA. It may be primary or secondary due to other pituitary disease, or hypothalamic dysfunction.	1.95	1	0
Chemical Dependence [description not available]	1.95	1	0
Drug Withdrawal Symptoms [description not available]	1.95	1	0
Substance Withdrawal Syndrome Physiological and psychological symptoms associated with withdrawal from the use of a drug after prolonged administration or habituation. The concept includes withdrawal from smoking or drinking, as well as withdrawal from an administered drug.	1.95	1	0
Substance-Related Disorders Disorders related to substance use or abuse.	1.95	1	0
Angor Pectoris [description not available]	1.95	1	0
Carditis [description not available]	1.95	1	0
Angina Pectoris The symptom of paroxysmal pain consequent to MYOCARDIAL ISCHEMIA usually of distinctive character, location and radiation. It is thought to be provoked by a transient stressful situation during which the oxygen requirements of the MYOCARDIUM exceed that supplied by the CORONARY CIRCULATION.	1.95	1	0
Myocarditis Inflammatory processes of the muscular walls of the heart (MYOCARDIUM) which result in injury to the cardiac muscle cells (MYOCYTES, CARDIAC). Manifestations range from subclinical to sudden death (DEATH, SUDDEN). Myocarditis in association with cardiac dysfunction is classified as inflammatory CARDIOMYOPATHY usually caused by INFECTION, autoimmune diseases, or responses to toxic substances. Myocarditis is also a common cause of DILATED CARDIOMYOPATHY and other cardiomyopathies.	1.95	1	0
Hypertension, Renal Persistent high BLOOD PRESSURE due to KIDNEY DISEASES, such as those involving the renal parenchyma, the renal vasculature, or tumors that secrete RENIN.	1.95	1	0
Arteriosclerosis Thickening and loss of elasticity of the walls of ARTERIES of all sizes. There are many forms classified by the types of lesions and arteries involved, such as ATHEROSCLEROSIS with fatty lesions in the ARTERIAL INTIMA of medium and large muscular arteries.	4.43	5	0
Asystole [description not available]	1.95	1	0
Heart Arrest Cessation of heart beat or MYOCARDIAL CONTRACTION. If it is treated within a few minutes, heart arrest can be reversed in most cases to normal cardiac rhythm and effective circulation.	1.95	1	0
Deficiency, Pyridoxine [description not available]	2.35	2	0
Leukemia, Lymphocytic [description not available]	1.95	1	0
Leukemia, Lymphoid Leukemia associated with HYPERPLASIA of the lymphoid tissues and increased numbers of circulating malignant LYMPHOCYTES and lymphoblasts.	1.95	1	0
Condition, Preneoplastic [description not available]	1.98	1	0
Precancerous Conditions Pathological conditions that tend eventually to become malignant.	1.98	1	0
Infections, Mycobacterium [description not available]	1.97	1	0
Mycobacterium Infections Infections with bacteria of the genus MYCOBACTERIUM.	1.97	1	0
Hypothermia, Accidental [description not available]	1.97	1	0
Hypothermia Lower than normal body temperature, especially in warm-blooded animals.	1.97	1	0
Muscle Disorders [description not available]	2.89	1	0
Muscular Diseases Acquired, familial, and congenital disorders of SKELETAL MUSCLE and SMOOTH MUSCLE.	2.89	1	0
Deficiency, Vitamin E [description not available]	1.97	1	0
Germinoblastoma [description not available]	1.97	1	0
Fibrosarcoma A sarcoma derived from deep fibrous tissue, characterized by bundles of immature proliferating fibroblasts with variable collagen formation, which tends to invade locally and metastasize by the bloodstream. (Stedman, 25th ed)	1.97	1	0
Lymphoma A general term for various neoplastic diseases of the lymphoid tissue.	1.97	1	0
Adverse Drug Event [description not available]	2.88	1	0
Disease A definite pathologic process with a characteristic set of signs and symptoms. It may affect the whole body or any of its parts, and its etiology, pathology, and prognosis may be known or unknown.	2.88	1	0
Drug-Related Side Effects and Adverse Reactions Disorders that result from the intended use of PHARMACEUTICAL PREPARATIONS. Included in this heading are a broad variety of chemically-induced adverse conditions due to toxicity, DRUG INTERACTIONS, and metabolic effects of pharmaceuticals.	2.88	1	0
Elevated Cholesterol [description not available]	2.36	2	0
Hypercholesterolemia A condition with abnormally high levels of CHOLESTEROL in the blood. It is defined as a cholesterol value exceeding the 95th percentile for the population.	2.36	2	0
Muscular Dystrophy [description not available]	1.97	1	0
Muscular Dystrophies A heterogeneous group of inherited MYOPATHIES, characterized by wasting and weakness of the SKELETAL MUSCLE. They are categorized by the sites of MUSCLE WEAKNESS; AGE OF ONSET; and INHERITANCE PATTERNS.	1.97	1	0
Cell Transformation, Viral An inheritable change in cells manifested by changes in cell division and growth and alterations in cell surface properties. It is induced by infection with a transforming virus.	1.96	1	0
Atypical Ductal Hyperplasia [description not available]	1.96	1	0
Carcinoma, Intraductal, Noninfiltrating A noninvasive (noninfiltrating) carcinoma of the breast characterized by a proliferation of malignant epithelial cells confined to the mammary ducts or lobules, without light-microscopy evidence of invasion through the basement membrane into the surrounding stroma.	1.96	1	0
Encephalomyelitis, Subacute Necrotizing [description not available]	3.29	2	0
Dyskinesia Syndromes [description not available]	2.88	1	0
Nervous System Disorders [description not available]	2.88	1	0
Leigh Disease A group of metabolic disorders primarily of infancy characterized by the subacute onset of psychomotor retardation, hypotonia, ataxia, weakness, vision loss, eye movement abnormalities, seizures, dysphagia, and lactic acidosis. Pathological features include spongy degeneration of the neuropile of the basal ganglia, thalamus, brain stem, and spinal cord. Patterns of inheritance include X-linked recessive, autosomal recessive, and mitochondrial. Leigh disease has been associated with mutations in genes for the PYRUVATE DEHYDROGENASE COMPLEX; CYTOCHROME-C OXIDASE; ATP synthase subunit 6; and subunits of mitochondrial complex I. (From Menkes, Textbook of Child Neurology, 5th ed, p850).	3.29	2	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.	2.88	1	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.	2.88	1	0
Acute Liver Injury, Drug-Induced [description not available]	2.65	3	0
Chemical and Drug Induced Liver Injury A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.	2.65	3	0
Cognition Disorders Disorders characterized by disturbances in mental processes related to learning, thinking, reasoning, and judgment.	2.88	1	0
Ataxia with Lactic Acidosis 2 [description not available]	1.96	1	0
Fat Necrosis A condition in which the death of adipose tissue results in neutral fats being split into fatty acids and glycerol.	1.97	1	0
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	3.29	2	0
Bacteroides Infections Infections with bacteria of the genus BACTEROIDES.	1.96	1	0
Abscess Accumulation of purulent material in tissues, organs, or circumscribed spaces, usually associated with signs of infection.	1.96	1	0
Acute Edematous Pancreatitis [description not available]	2.88	1	0
Pancreatitis INFLAMMATION of the PANCREAS. Pancreatitis is classified as acute unless there are computed tomographic or endoscopic retrograde cholangiopancreatographic findings of CHRONIC PANCREATITIS (International Symposium on Acute Pancreatitis, Atlanta, 1992). The two most common forms of acute pancreatitis are ALCOHOLIC PANCREATITIS and gallstone pancreatitis.	2.88	1	0
Glycosuria The appearance of an abnormally large amount of GLUCOSE in the urine, such as more than 500 mg/day in adults. It can be due to HYPERGLYCEMIA or genetic defects in renal reabsorption (RENAL GLYCOSURIA).	1.97	1	0
Circulatory Collapse [description not available]	1.96	1	0
Shock A pathological condition manifested by failure to perfuse or oxygenate vital organs.	1.96	1	0
Amyotonia Congenita [description not available]	1.97	1	0
Neuromuscular Diseases A general term encompassing lower MOTOR NEURON DISEASE; PERIPHERAL NERVOUS SYSTEM DISEASES; and certain MUSCULAR DISEASES. Manifestations include MUSCLE WEAKNESS; FASCICULATION; muscle ATROPHY; SPASM; MYOKYMIA; MUSCLE HYPERTONIA, myalgias, and MUSCLE HYPOTONIA.	1.97	1	0
Abnormalities, Drug-Induced Congenital abnormalities caused by medicinal substances or drugs of abuse given to or taken by the mother, or to which she is inadvertently exposed during the manufacture of such substances. The concept excludes abnormalities resulting from exposure to non-medicinal chemicals in the environment.	1.96	1	0
Deficiency, Vitamin B 12 [description not available]	2.35	2	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)	2.35	2	0
Avitaminosis A condition due to a deficiency of one or more essential vitamins. (Dorland, 27th ed)	1.95	1	0
Health Care Associated Infection [description not available]	1.95	1	0
Cross Infection Any infection which a patient contracts in a health-care institution.	1.95	1	0
Cirrhosis, Liver [description not available]	6.33	10	0
Malabsorption Syndromes General term for a group of MALNUTRITION syndromes caused by failure of normal INTESTINAL ABSORPTION of nutrients.	6.23	9	0
Batten Turner Congenital Myopathy [description not available]	6.23	9	0
Anorexia Nervosa An eating disorder that is characterized by the lack or loss of APPETITE, known as ANOREXIA. Other features include excess fear of becoming OVERWEIGHT; BODY IMAGE disturbance; significant WEIGHT LOSS; refusal to maintain minimal normal weight; and AMENORRHEA. This disorder occurs most frequently in adolescent females. (APA, Thesaurus of Psychological Index Terms, 1994)	6.23	9	0
Liver Cirrhosis Liver disease in which the normal microcirculation, the gross vascular anatomy, and the hepatic architecture have been variably destroyed and altered with fibrous septa surrounding regenerated or regenerating parenchymal nodules.	6.33	10	0
Hepatitis INFLAMMATION of the LIVER.	1.95	1	0
Arbovirus Infections Infections caused by arthropod-borne viruses, general or unspecified.	1.94	1	0
Injuries Used with anatomic headings, animals, and sports for wounds and injuries. Excludes cell damage, for which pathology is used.	1.94	1	0
Burns Injuries to tissues caused by contact with heat, steam, chemicals (BURNS, CHEMICAL), electricity (BURNS, ELECTRIC), or the like.	1.94	1	0
Wounds and Injuries Damage inflicted on the body as the direct or indirect result of an external force, with or without disruption of structural continuity.	1.94	1	0
Alcoholic Intoxication An acute brain syndrome which results from the excessive ingestion of ETHANOL or ALCOHOLIC BEVERAGES.	1.95	1	0
Acute Disease Disease having a short and relatively severe course.	1.95	1	0
Central Nervous System Disease [description not available]	1.95	1	0
Central Nervous System Diseases Diseases of any component of the brain (including the cerebral hemispheres, diencephalon, brain stem, and cerebellum) or the spinal cord.	1.95	1	0

acetyl coenzyme a

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