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

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
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 ChemicalBook:CB1454369, eMolecules:520938, MolPort-000-883-332, ZINC000000001669
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Formula C6H10O5
Net Charge 0
Average Mass 162.14060
Monoisotopic Mass 162.05282
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)
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 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
Manual Xrefs Databases
1670 DrugCentral
C00001187 KNApSAcK
C03761 KEGG COMPOUND
CPD-547 MetaCyc
D04897 KEGG DRUG
DB04377 DrugBank
HMDB0000355 HMDB
MAH PDBeChem
View more database links
Registry Numbers Types Sources
1769194 Reaxys Registry Number Reaxys
503-49-1 CAS Registry Number KEGG COMPOUND
503-49-1 CAS Registry Number ChemIDplus
Citations
Leipnitz G, Seminotti B, Haubrich J, Dalcin MB, Dalcin KB, Solano A, de Bortoli G, Rosa RB, Amaral AU, Dutra-Filho CS, Latini A, Wajner M (2008)
Evidence that 3-hydroxy-3-methylglutaric acid promotes lipid and protein oxidative damage and reduces the nonenzymatic antioxidant defenses in rat cerebral cortex.
Journal of neuroscience research 86, 683-693 [PubMed:17941049]
[show Abstract]
Koling S, Kalhoff H, Schauerte P, Lehnert W, Diekmann L (2000)
[3-hydroxy-3-methylglutaraciduria (case report of a female Turkish sisters with 3-hydroxy-3- methylglutaryl-Coenzyme A lyase deficiency].
Klinische Padiatrie 212, 113-116 [PubMed:10916782]
[show Abstract]
Eirís J, Ribes A, Fernández-Prieto R, Rodríguez-García J, Rodríguez-Segade S, Castro-Gago M (1998)
[3-hydroxy-3-methylglutaric aciduria and recurrent Reye-like syndrome].
Revista de neurologia 26, 911-914 [PubMed:9658458]
[show Abstract]
Gibson KM, Breuer J, Nyhan WL (1988)
3-Hydroxy-3-methylglutaryl-coenzyme A lyase deficiency: review of 18 reported patients.
European journal of pediatrics 148, 180-186 [PubMed:3063529]
[show Abstract]
Di Padova C, Di Padova F, Buzzetti M, Tritapepe R (1984)
Effect of 3-hydroxy-3-methylglutaric acid administration on bile lipid composition in humans.
Scandinavian journal of gastroenterology 19, 820-823 [PubMed:6083597]
[show Abstract]
Ahmad N, Siddiqi M (1973)
Bacterial metabolism of 3-hydroxy-3-methylglutaric acid.
Journal of bacteriology 115, 162-167 [PubMed:4717513]
[show Abstract]
Last Modified
20 November 2018