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
References
1. Hartman GD, Halczenko W, Duggan ME, Imagire JS, Smith RL, Pitzenberger SM, Fitzpatrick SL, Alberts AW, Bostedor R, Chao YS. (1992)
3-Hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors. 9. The synthesis and biological evaluation of novel simvastatin analogs.
J. Med. Chem., 35 (21): 3813-21. [PMID:1433193]
2. Hoffman WF, Alberts AW, Anderson PS, Chen JS, Smith RL, Willard AK. (1986)
3-Hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors. 4. Side chain ester derivatives of mevinolin.
J. Med. Chem., 29 (5): 849-52. [PMID:3634830]
3. Istvan ES, Deisenhofer J. (2001)
Structural mechanism for statin inhibition of HMG-CoA reductase.
Science, 292 (5519): 1160-4. [PMID:11349148]
4. McTaggart F, Buckett L, Davidson R, Holdgate G, McCormick A, Schneck D, Smith G, Warwick M. (2001)
Preclinical and clinical pharmacology of Rosuvastatin, a new 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitor.
Am. J. Cardiol., 87 (5A): 28B-32B. [PMID:11256847]
5. Pfefferkorn JA, Song Y, Sun KL, Miller SR, Trivedi BK, Choi C, Sorenson RJ, Bratton LD, Unangst PC, Larsen SD et al.. (2007)
Design and synthesis of hepatoselective, pyrrole-based HMG-CoA reductase inhibitors.
Bioorg. Med. Chem. Lett., 17 (16): 4538-44. [PMID:17574412]