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Substrate Report for: Simvastatin

Name Class
SimvastatinTypeDrug
Not A/B H target
Naphthalen
Other_NameZocor
Synvinolin
Sinvacor
Denan
Chemical_Nomenclature[(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
FormulaC25H38O5
CAS_number79902-63-9
MW418.57
PaperKnobloch_2016_Eur.J.Pharmacol_788_294
Wang_2015_Biol.Pharm.Bull_38_292
Li_2019_J.Pharm.Biomed.Anal_168_13
CommentSimvastatin is a lipid-lowering agent derived synthetically from a fermentation product of the fungus Aspergillus terreus. Hydrolyzed in vivo to an active metabolite, simvastatin competitively inhibits hepatic hydroxymethyl-glutaryl coenzyme A (HMG-CoA) reductase, the enzyme which catalyzes the conversion of HMG-CoA to mevalonate, a key step in cholesterol synthesis. This agent lowers plasma cholesterol and lipoprotein levels, and modulates immune responses by suppressing MHC II (major histocompatibility complex II) on interferon gamma-stimulated, antigen-presenting cells such as human vascular endothelial cells. Simvastatin is a prodrug hydrolysed by carboxylesterases. Simvastatin is a substrate of PON1, CES1b, PON3 and CES1c
Gene_locushuman-CES1
mouse-Ces1b
mouse-Ces1c
CID54454
FamilyCarb_B_Chordata
InChIKeyRYMZZMVNJRMUDD-HGQWONQESA-N
CanonicalSMILESCCC(C)(C)C(=O)OC1CC(C=C2C1C(C(C=C2)C)CCC3CC(CC(=O)O3)O)C
InChIInChI=1S/C25H38O5/c1-6-25(4,5)24(28)30-21-12-15(2)11-17-8-7-16(3)20(23(17)21)10-9-19-13-18(26)14-22(27)29-19/h7-8,11,15-16,18-21,23,26H,6,9-10,12-14H2,1-5H3/t15-,16-,18+,19+,20-,21-,23-/m0/s1

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Please cite: Lenfant 2013 Nucleic.Acids.Res. or Marchot Chatonnet 2012 Prot.Pept Lett.
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