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
SMILES / InChI / InChIKey
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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
InChI Key JTZZSQYMACOLNN-VDWJNHBNSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2013), EMA (2014))
International Nonproprietary Names Click here for help
INN number INN
9432 simeprevir
Synonyms Click here for help
Olysio® | simeprevir sodium | TMC 435 | TMC 435350 | TMC-435 | TMC435
Database Links Click here for help
CAS Registry No. 923604-59-5 (source: Scifinder)
ChEMBL Ligand CHEMBL501849
DrugBank Ligand DB06290
DrugCentral Ligand 4812
GtoPdb PubChem SID 178103939
PubChem CID 24873435
RCSB PDB Ligand 30B
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Wikipedia Simeprevir