CHEBI:82985 - mevinolinic acid

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ChEBI Name mevinolinic acid
ChEBI ID CHEBI:82985
Definition A polyketide obtained by hydrolysis of the pyranone ring of lovastatin.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C24H38O6
Net Charge 0
Average Mass 422.55490
Monoisotopic Mass 422.26684
InChI InChI=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
InChIKey QLJODMDSTUBWDW-BXMDZJJMSA-N
SMILES CC[C@H](C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@@H]12
Metabolite of Species Details
Aspergillus terreus (NCBI:txid33178) of strain ATCC 20542 See: PubMed
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): Aspergillus metabolite
Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
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.
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.
drug metabolite

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ChEBI Ontology
Outgoing 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 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 Sources
L 154819 ChemIDplus
L-154819 ChemIDplus
Lovastatin acid ChemIDplus
MK 819 ChemIDplus
Monacolinic K acid ChemIDplus
MSD 803 acid ChemIDplus
Registry Numbers Types Sources
4574661 Reaxys Registry Number Reaxys
75225-51-3 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11372002 PubMed citation Europe PMC
11831543 PubMed citation Europe PMC
12369143 PubMed citation Europe PMC
12434405 PubMed citation Europe PMC
12927388 PubMed citation Europe PMC
19530726 PubMed citation Europe PMC
22995742 PubMed citation Europe PMC
23227093 PubMed citation Europe PMC
23352857 PubMed citation Europe PMC
24534845 PubMed citation Europe PMC
24990555 PubMed citation Europe PMC
3988710 PubMed citation Europe PMC
6665743 PubMed citation Europe PMC
9050262 PubMed citation Europe PMC
9585793 PubMed citation Europe PMC
Last Modified
18 September 2014