simvastatin   

GtoPdb Ligand ID: 2955

Synonyms: MK-733 | Zocor®
simvastatin is an approved drug (FDA (1991), EMA (2013))
Compound class: Synthetic organic
Comment: Simvastatin is a statin class anti-dyslipidemia drug. It is synthetically derived from a fermantation product from Aspergillus terreus.
Simvastatin is on the World Health Organisation's List of Essential Medicines. Click here to access the pdf version of the WHO's 21st Essential Medicines list (2019).
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 72.83
Molecular weight 418.27
XLogP 4.78
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CCC(C(=O)OC1CC(C)C=C2C1C(CCC1CC(O)CC(=O)O1)C(C=C2)C)(C)C
Isomeric SMILES CCC(C(=O)O[C@H]1C[C@@H](C)C=C2[C@H]1[C@@H](CC[C@@H]1C[C@@H](O)CC(=O)O1)[C@H](C=C2)C)(C)C
InChI InChI=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
InChI Key RYMZZMVNJRMUDD-HGQWONQESA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1991), EMA (2013))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name
[(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
International Nonproprietary Names
INN number INN
6147 simvastatin
Synonyms
MK-733 | Zocor®
Database Links
CAS Registry No. 79902-63-9 (source: Scifinder)
ChEBI CHEBI:9150
ChEMBL Ligand CHEMBL1064
DrugBank Ligand DB00641
DrugCentral Ligand 2445
GtoPdb PubChem SID 135651045
PubChem CID 54454
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Wikipedia Simvastatin

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Tocris
Simvastatin
Cat. No. 1965