grazoprevir   Click here for help

GtoPdb Ligand ID: 11573

Synonyms: analog 15 [PMID: 24900473] | MK-5172 | MK5172 | Zepatier® [elbasvir (NS5A inhibitor) + grazoprevir]
Approved drug PDB Ligand
grazoprevir is an approved drug (FDA (2016), UK (2021))
Compound class: Synthetic organic
Comment: Grazoprevir (MK-5172) is an HCV NS3/4A protease inhibitor class antiviral drug [2]. In vitro evidence of activity against SARS-CoV-2 helicase [1] and papain-like protease (PLpro) [3].
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 13
Hydrogen bond donors 3
Rotatable bonds 10
Topological polar surface area 203.6
Molecular weight 766.34
XLogP 4.05
No. Lipinski's rules broken 1
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]2CN1C(=O)[C@@H](NC(=O)O[C@@H]1C[C@H]1CCCCCc1c(O2)nc2cc(OC)ccc2n1)C(C)(C)C)C(=O)NS(=O)(=O)C1CC1
Isomeric SMILES C=C[C@@H]1C[C@]1(NC(=O)[C@@H]1C[C@@H]2CN1C(=O)[C@@H](NC(=O)O[C@@H]1C[C@H]1CCCCCc1c(O2)nc2cc(OC)ccc2n1)C(C)(C)C)C(=O)NS(=O)(=O)C1CC1
InChI InChI=1S/C38H50N6O9S/c1-6-22-19-38(22,35(47)43-54(49,50)25-13-14-25)42-32(45)29-18-24-20-44(29)34(46)31(37(2,3)4)41-36(48)53-30-16-21(30)10-8-7-9-11-27-33(52-24)40-28-17-23(51-5)12-15-26(28)39-27/h6,12,15,17,21-22,24-25,29-31H,1,7-11,13-14,16,18-20H2,2-5H3,(H,41,48)(H,42,45)(H,43,47)/t21-,22-,24-,29+,30-,31-,38-/m1/s1
InChI Key OBMNJSNZOWALQB-NCQNOWPTSA-N
References
1. Abidi SH, Almansour NM, Amerzhanov D, Allemailem KS, Rafaqat W, Ibrahim MAA, la Fleur P, Lukac M, Ali S. (2021)
Repurposing potential of posaconazole and grazoprevir as inhibitors of SARS-CoV-2 helicase.
Sci Rep, 11 (1): 10290. DOI: 10.1038/s41598-021-89724-0 [PMID:33986405]
2. Harper S, McCauley JA, Rudd MT, Ferrara M, DiFilippo M, Crescenzi B, Koch U, Petrocchi A, Holloway MK, Butcher JW et al.. (2012)
Discovery of MK-5172, a Macrocyclic Hepatitis C Virus NS3/4a Protease Inhibitor.
ACS Med Chem Lett, 3 (4): 332-6. [PMID:24900473]
3. Mohamed K, Yazdanpanah N, Saghazadeh A, Rezaei N. (2021)
Computational drug discovery and repurposing for the treatment of COVID-19: A systematic review.
Bioorg Chem, 106: 104490. [PMID:33261845]