simeprevir   Click here for help

GtoPdb Ligand ID: 7367

Synonyms: Olysio® | simeprevir sodium | TMC 435 | TMC 435350 | TMC-435 | TMC435
Approved drug PDB Ligand
simeprevir is an approved drug (FDA (2013), EMA (2014))
Compound class: Synthetic organic
Comment: Simeprevir is a hepatitis C virus NS3/4A protease inhibitor.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 10
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 193.51
Molecular weight 749.29
XLogP 3.33
No. Lipinski's rules broken 0
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Canonical SMILES COc1ccc2c(c1C)nc(cc2OC1CC2C(C1)C(=O)N(C)CCCCC=CC1C(NC2=O)(C1)C(=O)NS(=O)(=O)C1CC1)c1scc(n1)C(C)C
Isomeric SMILES COc1ccc2c(c1C)nc(cc2O[C@@H]1C[C@@H]2[C@@H](C1)C(=O)N(C)CCCC/C=C\[C@H]1[C@](NC2=O)(C1)C(=O)NS(=O)(=O)C1CC1)c1scc(n1)C(C)C
InChI InChI=1S/C38H47N5O7S2/c1-21(2)30-20-51-35(40-30)29-18-32(26-13-14-31(49-5)22(3)33(26)39-29)50-24-16-27-28(17-24)36(45)43(4)15-9-7-6-8-10-23-19-38(23,41-34(27)44)37(46)42-52(47,48)25-11-12-25/h8,10,13-14,18,20-21,23-25,27-28H,6-7,9,11-12,15-17,19H2,1-5H3,(H,41,44)(H,42,46)/b10-8-/t23-,24-,27-,28-,38-/m1/s1
1. Raboisson P, de Kock H, Rosenquist A, Nilsson M, Salvador-Oden L, Lin TI, Roue N, Ivanov V, Wähling H, Wickström K et al.. (2008)
Structure-activity relationship study on a novel series of cyclopentane-containing macrocyclic inhibitors of the hepatitis C virus NS3/4A protease leading to the discovery of TMC435350.
Bioorg Med Chem Lett, 18 (17): 4853-8. [PMID:18678486]