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CHEBI:39508 - mevinic acid

ChEBI IDCHEBI:39508
ChEBI Namemevinic acid
Stars
DefinitionA 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.
Last Modified23 September 2018
DownloadsMolfile
FormulaC23H36O6
Net Charge0
Average Mass408.535
Monoisotopic Mass408.25119
SMILES[H][C@@]12C(=CCC[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/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
InChIKeyBOZILQFLQYBIIY-INTXDZFKSA-N
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
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.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
mevastatin (acid form)ChemIDplus
ML 236B acidChemIDplus
mevastatin hydroxy acidChemIDplus
ML-236B acidChemIDplus
compactin acidChemIDplus
mevastatin acidChemIDplus
Manual XrefsDatabases
114PDBeChem
EP0401784Patent
EP0428094Patent
Registry NumbersSources
CAS:84064-38-0ChemIDplus
Citations