EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:82985 - mevinolinic acid

ChEBI IDCHEBI:82985
ChEBI Namemevinolinic acid
Stars
DefinitionA polyketide obtained by hydrolysis of the pyranone ring of lovastatin.
Last Modified18 September 2014
SubmitterSteve
DownloadsMolfile
FormulaC24H38O6
Net Charge0
Average Mass422.562
Monoisotopic Mass422.26684
SMILES[H][C@@]12C(=C[C@H](C)C[C@@H]1OC(=O)[C@@H](C)CC)C=C[C@H](C)[C@@H]2CC[C@@H](O)C[C@@H](O)CC(=O)O
InChIInChI=1S/C24H38O6/c1-5-15(3)24(29)30-21-11-14(2)10-17-7-6-16(4)20(23(17)21)9-8-18(25)12-19(26)13-22(27)28/h6-7,10,14-16,18-21,23,25-26H,5,8-9,11-13H2,1-4H3,(H,27,28)/t14-,15-,16-,18+,19+,20-,21-,23-/m0/s1
InChIKeyQLJODMDSTUBWDW-BXMDZJJMSA-N
Species of MetaboliteComponentSourceComments
Aspergillus terreus (ncbitaxon:33178) - PubMed (24534845) Strain: ATCC 20542
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
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.
Aspergillus metabolite  Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
teratogenic agent  A role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect.
ChEBI Ontology
Outgoing Relation(s)
mevinolinic acid (CHEBI:82985) has functional parent (S)-2-methylbutyric acid (CHEBI:38655)
mevinolinic acid (CHEBI:82985) has functional parent lovastatin (CHEBI:40303)
mevinolinic acid (CHEBI:82985) has role Aspergillus metabolite (CHEBI:76956)
mevinolinic acid (CHEBI:82985) has role drug metabolite (CHEBI:49103)
mevinolinic acid (CHEBI:82985) has role EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor (CHEBI:35664)
mevinolinic acid (CHEBI:82985) has role teratogenic agent (CHEBI:50905)
mevinolinic acid (CHEBI:82985) is a carbobicyclic compound (CHEBI:36785)
mevinolinic acid (CHEBI:82985) is a dihydroxy monocarboxylic acid (CHEBI:35972)
mevinolinic acid (CHEBI:82985) is a fatty acid ester (CHEBI:35748)
mevinolinic acid (CHEBI:82985) is a polyketide (CHEBI:26188)
mevinolinic acid (CHEBI:82985) is conjugate acid of mevinolinate (CHEBI:79038)
Incoming Relation(s)
mevinolinate (CHEBI:79038) is conjugate base of mevinolinic acid (CHEBI:82985)
IUPAC Name 
(3R,5R)-7-[(1S,2S,6R,8S,8aR)-2,6-dimethyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid
Synonyms  Source
Lovastatin acidChemIDplus
L-154819ChemIDplus
Monacolinic K acidChemIDplus
MSD 803 acidChemIDplus
MK 819ChemIDplus
L 154819ChemIDplus
Registry NumbersSources
Reaxys:4574661Reaxys
CAS:75225-51-3ChemIDplus
Citations