asunaprevir   

GtoPdb Ligand ID: 10882

Synonyms: BMS-650032 | BMS650032 | compound 24 [PMID: 24564672] | Sunvepra™
asunaprevir is an approved drug (Japan (2014), Canada (2016))
Compound class: Synthetic organic
Comment: Asunaprevir (BMS-650032) is an orally bioavailable, oligopeptide-based inhibitor of the nonstructural protein 3 (NS3), from hepatitis C virus (HCV) [4]. NS3, is a serine protease that is essential for proteolytic cleavages within the HCV polyprotein, a function that is key during HCV viral RNA replication. More recently asunaprevir has been reported to inhibit the papain-like protease (PL-pro, nsp3) in a number of coronaviruses [2].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 12
Hydrogen bond donors 3
Rotatable bonds 18
Topological polar surface area 190.71
Molecular weight 747.27
XLogP 4.41
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Canonical SMILES C=C[C@@H]1C[C@]1(NC(=O)[C@@H]1C[C@H](CN1C(=O)[C@H](C(C)(C)C)NC(=O)OC(C)(C)C)Oc1ncc(c2c1cc(Cl)cc2)OC)C(=O)NS(=O)(=O)C1CC1
Isomeric SMILES C=C[C@@H]1C[C@]1(NC(=O)[C@@H]1C[C@H](CN1C(=O)[C@H](C(C)(C)C)NC(=O)OC(C)(C)C)Oc1ncc(c2c1cc(Cl)cc2)OC)C(=O)NS(=O)(=O)C1CC1
InChI InChI=1S/C35H46ClN5O9S/c1-9-19-16-35(19,31(44)40-51(46,47)22-11-12-22)39-28(42)25-15-21(49-29-24-14-20(36)10-13-23(24)26(48-8)17-37-29)18-41(25)30(43)27(33(2,3)4)38-32(45)50-34(5,6)7/h9-10,13-14,17,19,21-22,25,27H,1,11-12,15-16,18H2,2-8H3,(H,38,45)(H,39,42)(H,40,44)/t19-,21-,25+,27-,35-/m1/s1
InChI Key XRWSZZJLZRKHHD-WVWIJVSJSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (Japan (2014), Canada (2016))
IUPAC Name
tert-butyl N-[(2S)-1-[(2S,4R)-4-(7-chloro-4-methoxyisoquinolin-1-yl)oxy-2-[[(1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-ethenylcyclopropyl]carbamoyl]pyrrolidin-1-yl]-3,3-dimethyl-1-oxobutan-2-yl]carbamate
International Nonproprietary Names
INN number INN
9472 asunaprevir
Synonyms
BMS-650032 | BMS650032 | compound 24 [PMID: 24564672] | Sunvepra™
Database Links
CAS Registry No. 630420-16-5 (source: WHO INN recod)
ChEMBL Ligand CHEMBL2105735
DrugBank Ligand DB11586
GtoPdb PubChem SID 405560323
PubChem CID 16076883
RCSB PDB Ligand 2R9
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