asunaprevir   Click here for help

GtoPdb Ligand ID: 10882

Synonyms: BMS-650032 | BMS650032 | compound 24 [PMID: 24564672] | Sunvepra™
Approved drug PDB Ligand
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].
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
References
1. Akamatsu N, Sugawara Y, Kokudo N. (2015)
Asunaprevir (BMS-650032) for the treatment of hepatitis C virus.
Expert Rev Anti Infect Ther, 13 (11): 1307-17. [PMID:26414905]
2. Anson BJ, Chapman ME, Lendy EK, Pshenychnyi S, D’Aquila RT, Satchell KJF, Mesecar AD. (2020)
Broad-spectrum inhibition of coronavirus main and papain-like proteases by HCV drugs.
Nature Research, PrePrint, Under Review. DOI: 10.21203/rs.3.rs-26344/v1
3. Bristol Myers Squibb. 
Bristol-Myers Squibb Statement about Asunaprevir in the U.S.
Accessed on 19/05/2020. Modified on 19/05/2020. news.bms.com, https://news.bms.com/press-release/rd-news/bristol-myers-squibb-statement-about-asunaprevir-us
4. Scola PM, Sun LQ, Wang AX, Chen J, Sin N, Venables BL, Sit SY, Chen Y, Cocuzza A, Bilder DM et al.. (2014)
The discovery of asunaprevir (BMS-650032), an orally efficacious NS3 protease inhibitor for the treatment of hepatitis C virus infection.
J Med Chem, 57 (5): 1730-52. [PMID:24564672]