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CHEBI:16831 - 3-hydroxy-3-methylglutaric acid

ChEBI IDCHEBI:16831
ChEBI Name3-hydroxy-3-methylglutaric acid
Stars
DefinitionA 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.
Secondary ChEBI IDsCHEBI:391, CHEBI:1524, CHEBI:11044, CHEBI:18746, CHEBI:20043, CHEBI:30919, CHEBI:43804
Last Modified20 November 2018
SubmitterKirill Degtyarenko
DownloadsMolfile
FormulaC6H10O5
Net Charge0
Average Mass162.141
Monoisotopic Mass162.05282
SMILESCC(O)(CC(=O)O)CC(=O)O
InChIInChI=1S/C6H10O5/c1-6(11,2-4(7)8)3-5(9)10/h11H,2-3H2,1H3,(H,7,8)(H,9,10)
InChIKeyNPOAOTPXWNWTSH-UHFFFAOYSA-N
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
human metabolite  Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
antimetabolite  A substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization.
EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor  Any EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that inhibits HMG-CoA reductases. Hydroxymethylglutaryl-CoA reductase inhibitors have been shown to lower directly cholesterol synthesis. The Enzyme Commission designation is EC 1.1.1.34 for the NADPH-dependent enzyme and EC 1.1.1.88 for an NADH-dependent enzyme.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application:
anticholesteremic drug  A substance used to lower plasma cholesterol levels.
ChEBI Ontology
Outgoing Relation(s)
3-hydroxy-3-methylglutaric acid (CHEBI:16831) has functional parent glutaric acid (CHEBI:17859)
3-hydroxy-3-methylglutaric acid (CHEBI:16831) has role anticholesteremic drug (CHEBI:35821)
3-hydroxy-3-methylglutaric acid (CHEBI:16831) has role antimetabolite (CHEBI:35221)
3-hydroxy-3-methylglutaric acid (CHEBI:16831) has role EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor (CHEBI:35664)
3-hydroxy-3-methylglutaric acid (CHEBI:16831) has role human metabolite (CHEBI:77746)
3-hydroxy-3-methylglutaric acid (CHEBI:16831) has role plant metabolite (CHEBI:76924)
3-hydroxy-3-methylglutaric acid (CHEBI:16831) is a 3-hydroxy carboxylic acid (CHEBI:61355)
3-hydroxy-3-methylglutaric acid (CHEBI:16831) is a dicarboxylic acid (CHEBI:35692)
3-hydroxy-3-methylglutaric acid (CHEBI:16831) is a tertiary alcohol (CHEBI:26878)
3-hydroxy-3-methylglutaric acid (CHEBI:16831) is conjugate acid of 3-hydroxy-3-methylglutarate(1−) (CHEBI:30920)
Incoming Relation(s)
3-hydroxy-3-methylglutaryl-CoA (CHEBI:11814) has functional parent 3-hydroxy-3-methylglutaric acid (CHEBI:16831)
dianversicoside A (CHEBI:65755) has functional parent 3-hydroxy-3-methylglutaric acid (CHEBI:16831)
dianversicoside B (CHEBI:65756) has functional parent 3-hydroxy-3-methylglutaric acid (CHEBI:16831)
dianversicoside C (CHEBI:65757) has functional parent 3-hydroxy-3-methylglutaric acid (CHEBI:16831)
dianversicoside D (CHEBI:65758) has functional parent 3-hydroxy-3-methylglutaric acid (CHEBI:16831)
licoagroside B (CHEBI:142266) has functional parent 3-hydroxy-3-methylglutaric acid (CHEBI:16831)
viscumneoside IV (CHEBI:132858) has functional parent 3-hydroxy-3-methylglutaric acid (CHEBI:16831)
viscumneoside VII (CHEBI:132861) has functional parent 3-hydroxy-3-methylglutaric acid (CHEBI:16831)
yanuthone D (CHEBI:133841) has functional parent 3-hydroxy-3-methylglutaric acid (CHEBI:16831)
yanuthone E (CHEBI:133840) has functional parent 3-hydroxy-3-methylglutaric acid (CHEBI:16831)
yanuthone J (CHEBI:133838) has functional parent 3-hydroxy-3-methylglutaric acid (CHEBI:16831)
3-hydroxy-3-methylglutarate(1−) (CHEBI:30920) is conjugate base of 3-hydroxy-3-methylglutaric acid (CHEBI:16831)
IUPAC Name 
3-hydroxy-3-methylpentanedioic acid
INNs  Source
meglutolChemIDplus
meglutolWHO MedNet
méglutolWHO MedNet
meglutolumWHO MedNet
Synonyms  Source
3-HYDROXY-3-METHYL-GLUTARIC ACIDPDBeChem
3-Hydroxy-3-methylpentanedioic acidKEGG COMPOUND
beta-Hydroxy-beta-methylglutaric acidKEGG COMPOUND
Dicrotalic acidKEGG COMPOUND
(S)-3-Hydroxy-3-methylglutaric acidKEGG COMPOUND
(S)-MeglutolKEGG COMPOUND
Manual XrefsDatabases
1670DrugCentral
C00001187KNApSAcK
C03761KEGG COMPOUND
CPD-547MetaCyc
D04897KEGG DRUG
DB04377DrugBank
HMDB0000355HMDB
MAHPDBeChem
Registry NumbersSources
Reaxys:1769194Reaxys
CAS:503-49-1ChemIDplus
CAS:503-49-1KEGG COMPOUND
Citations