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

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ChEBI Name 3-hydroxy-3-methylglutaric acid
ChEBI ID CHEBI:16831
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:391, CHEBI:1524, CHEBI:20043, CHEBI:43804, CHEBI:11044, CHEBI:30919, CHEBI:18746
Supplier Information
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Formula C6H10O5
Net Charge 0
Average Mass 162.14060
Monoisotopic Mass 162.053
InChI InChI=1S/C6H10O5/c1-6(11,2-4(7)8)3-5(9)10/h11H,2-3H2,1H3,(H,7,8)(H,9,10)
InChIKey NPOAOTPXWNWTSH-UHFFFAOYSA-N
SMILES CC(O)(CC(O)=O)CC(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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.
Application(s): anticholesteremic drug
A substance used to lower plasma cholesterol levels.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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)
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 Sources
meglutol ChemIDplus
méglutol WHO MedNet
meglutol WHO MedNet
meglutolum WHO MedNet
Synonyms Sources
(S)-3-Hydroxy-3-methylglutaric acid KEGG COMPOUND
(S)-Meglutol KEGG COMPOUND
3-HYDROXY-3-METHYL-GLUTARIC ACID PDBeChem
3-Hydroxy-3-methylpentanedioic acid KEGG COMPOUND
beta-Hydroxy-beta-methylglutaric acid KEGG COMPOUND
β-hydroxy-β-methylglutaric acid ChEBI
Dicrotalic acid KEGG COMPOUND
Database Links Databases
1670 DrugCentral
C00001187 KNApSAcK
C03761 KEGG COMPOUND
CPD-547 MetaCyc
D04897 KEGG DRUG
DB04377 DrugBank
HMDB00355 HMDB
MAH PDBeChem
View more database links
Registry Numbers Types Sources
1769194 Beilstein Registry Number Beilstein
1769194 Reaxys Registry Number Reaxys
503-49-1 CAS Registry Number KEGG COMPOUND
503-49-1 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10916782 PubMed citation Europe PMC
17941049 PubMed citation Europe PMC
3063529 PubMed citation Europe PMC
4717513 PubMed citation Europe PMC
6083597 PubMed citation Europe PMC
9658458 PubMed citation Europe PMC
Last Modified
22 February 2017