Mevinic Acid

HCID 446154CAS 84064-38-0

基本情報

標準SMILES: CC[C@H](C)C(=O)O[C@H]1CCC=C2C=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(=O)O)[C@H]21
InChIKey: BOZILQFLQYBIIY-INTXDZFKSA-N
分子式: C23H36O6
平均分子量: 408.5 g/mol

概要

Mevinic acid is 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. It has a role as an EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor. It is a member of hexahydronaphthalenes, a polyketide, a carboxylic ester and a 3-hydroxy carboxylic acid. It is a conjugate acid of a mevinic acid anion.

名称と識別子

優先名称: Mevinic Acid
IUPAC: (3R,5R)-7-[(1S,2S,8S,8aR)-2-methyl-8-[(2S)-2-methylbutanoyl]oxy-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid

名称と別名

Mevinic acidMevastatin acidCompactin acidMevastatin hydroxy acidMevastatin (acid form)ML 236B acid1R89KK61YIML-236B acid84064-38-0UNII-1R89KK61YICHEBI:39508(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

名称をさらに表示

(3R,5R)-7-[(1S,2S,8S,8aR)-2-methyl-8-[(2S)-2-methylbutanoyl]oxy-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid1-Naphthaleneheptanoic acid, 1,2,6,7,8,8a-hexahydro-beta,delta-dihydroxy-2-methyl-8-((2S)-2-methyl-1-oxobutoxy)-, (betaR,deltaR,1S,2S,8S,8aR)-1-NAPHTHALENEHEPTANOIC ACID, 1,2,6,7,8,8A-HEXAHYDRO-.BETA.,.DELTA.-DIHYDROXY-2-METHYL-8-((2S)-2-METHYL-1-OXOBUTOXY)-, (.BETA.R,.DELTA.R,1S,2S,8S,8AR)-DTXSID40875476(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(3R,5R)-7-((1S,2S,8S,8aR)-2-methyl-8-((2S)-2-methylbutanoyl)oxy-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)-3,5-dihydroxyheptanoic acidRefChem:158427DTXCID70950649

データベース識別子

CAS: 84064-38-0
PubChem CID: 446154
ChEMBL: CHEMBL503456
ChEBI: CHEBI:39508
UNII: 1R89KK61YI
Nikkaji: J386.673D

物性

構造計算による物性

XLogP: 3.1
極性表面積: 104 Å²
水素結合供与体数: 3
水素結合受容体数: 6
回転可能結合数: 11
重原子数: 29
形式電荷: 0
複雑度: 625