CHEBI:39508 - mevinic acid

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ChEBI Name mevinic acid
ChEBI ID CHEBI:39508
Definition A member of the class of hexahydronaphthalenes that is 1,2,6,7,8,8a-hexahydronaphthalene which is substituted by a (3R,5R)-6-carboxy-3,5-dihydroxyhexyl group at position 1, a methyl group at position 2, and a (2S)-2-methylbutanoyloxy group at position 8 (the 1S,2S,8S,8aR isomer). Lactonisation of the hydroxy-carboxylic acid chain at position 1 affords mevastatin.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C23H36O6
Net Charge 0
Average Mass 408.529
Monoisotopic Mass 408.25119
InChI InChI=1S/C23H36O6/c1-4-14(2)23(28)29-20-7-5-6-16-9-8-15(3)19(22(16)20)11-10-17(24)12-18(25)13-21(26)27/h6,8-9,14-15,17-20,22,24-25H,4-5,7,10-13H2,1-3H3,(H,26,27)/t14-,15-,17+,18+,19-,20-,22-/m0/s1
InChIKey BOZILQFLQYBIIY-INTXDZFKSA-N
SMILES [C@@]12([C@H](CCC=C1C=C[C@@H]([C@@H]2CC[C@H](C[C@H](CC(=O)O)O)O)C)OC([C@H](CC)C)=O)[H]
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): 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.
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ChEBI Ontology
Outgoing mevinic acid (CHEBI:39508) has role EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor (CHEBI:35664)
mevinic acid (CHEBI:39508) is a 3-hydroxy carboxylic acid (CHEBI:61355)
mevinic acid (CHEBI:39508) is a carboxylic ester (CHEBI:33308)
mevinic acid (CHEBI:39508) is a hexahydronaphthalenes (CHEBI:142348)
mevinic acid (CHEBI:39508) is a polyketide (CHEBI:26188)
mevinic acid (CHEBI:39508) is conjugate acid of mevinic acid anion (CHEBI:142050)
Incoming mevinic acid anion (CHEBI:142050) is conjugate base of mevinic acid (CHEBI:39508)
IUPAC Name
(3R,5R)-3,5-dihydroxy-7-[(1S,2S,8S,8aR)-2-methyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]heptanoic acid
Synonyms Sources
compactin acid ChemIDplus
mevastatin (acid form) ChemIDplus
mevastatin acid ChemIDplus
mevastatin hydroxy acid ChemIDplus
ML 236B acid ChemIDplus
ML-236B acid ChemIDplus
Manual Xrefs Databases
114 PDBeChem
EP0401784 Patent
EP0428094 Patent
View more database links
Registry Number Type Source
84064-38-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
1010803 PubMed citation Europe PMC
16042349 PubMed citation Europe PMC
Last Modified
23 September 2018