Molecular Identity
Simvastatin
[(1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2,2-dimethylbutanoate
PubChem CID: 54454
Simvastatin is a member of the class of hexahydronaphthalenes that is lovastatin in which the 2-methylbutyrate ester moiety has been replaced by a 2,2-dimethylbutyrate ester group. It is used as a cholesterol-lowering and anti-cardiovascular disease drug. It has a role as a ferroptosis inducer, a geroprotector, an EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor, a prodrug and an EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor. It is a member of hexahydronaphthalenes, a delta-lactone, a fatty acid ester and a statin (semi-synthetic). It is functionally related to a lovastatin.
2D Structure
Properties
C25H38O5
Molecular Formula
418.60
Molecular Weight
g/mol
418.2719
Exact Mass
Da
4.7
XLogP
Drug-like (Lipinski: < 5)
72.8
TPSA
Good oral absorption (< 140 A²)
1
H-Bond Donors
5
H-Bond Acceptors
706
Complexity
SMILES
Canonical SMILES
SMILES: CCC(C)(C)C(=O)OC1CC(C=C2C1C(C(C=C2)C)CCC3CC(CC(=O)O3)O)CIsomeric SMILES
SMILES: CCC(C)(C)C(=O)O[C@H]1C[C@H](C=C2[C@H]1[C@H]([C@H](C=C2)C)CC[C@@H]3C[C@H](CC(=O)O3)O)CSynonyms(20)
simvastatin79902-63-9ZocorSynvinolinMK-733SinvacorDenanLipexSimvastatineSivastinLodalesCholestatSimvastatinaColeminMedipo
Data from PubChem (NCBI)
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Drug Network
Trials and conditions connected to Simvastatin
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