vaniprevir   Click here for help

GtoPdb Ligand ID: 11570

Synonyms: analog 35b [PMID: 20163176] | MK-7009 | MK7009 | Vanihep®
Approved drug PDB Ligand
vaniprevir is an approved drug (Japan 2014)
Compound class: Synthetic organic
Comment: Vaniprevir (MK-7009) is a non-covalent competitive, macrocyclic hepatitis C virus (HCV, genotype 1a and 1b) NS3/4A protease inhibitor [2-3]. It has also been reported to inhibit SARS CoV-2 papain-like protease (PL-pro) in vitro [1].
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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 14
Hydrogen bond donors 3
Rotatable bonds 9
Topological polar surface area 188.9
Molecular weight 757.37
XLogP 4.72
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CC[C@@H]1C[C@]1(NC(=O)[C@@H]1C[C@@H]2CN1C(=O)[C@@H](NC(=O)OCC(C)(C)CCCCc1c3CN(C(=O)O2)Cc3ccc1)C(C)(C)C)C(=O)NS(=O)(=O)C1CC1
Isomeric SMILES CC[C@@H]1C[C@]1(NC(=O)[C@@H]1C[C@@H]2CN1C(=O)[C@@H](NC(=O)OCC(C)(C)CCCCc1c3CN(C(=O)O2)Cc3ccc1)C(C)(C)C)C(=O)NS(=O)(=O)C1CC1
InChI InChI=1S/C38H55N5O9S/c1-7-25-18-38(25,33(46)41-53(49,50)27-14-15-27)40-31(44)29-17-26-20-43(29)32(45)30(36(2,3)4)39-34(47)51-22-37(5,6)16-9-8-11-23-12-10-13-24-19-42(21-28(23)24)35(48)52-26/h10,12-13,25-27,29-30H,7-9,11,14-22H2,1-6H3,(H,39,47)(H,40,44)(H,41,46)/t25-,26-,29+,30-,38-/m1/s1
InChI Key KUQWGLQLLVFLSM-ONAXAZCASA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (Japan 2014)
IUPAC Name Click here for help
(1R,21S,24S)-21-tert-butyl-N-[(1R,2R)-1-(cyclopropylsulfonylcarbamoyl)-2-ethylcyclopropyl]-16,16-dimethyl-3,19,22-trioxo-2,18-dioxa-4,20,23-triazatetracyclo[21.2.1.14,7.06,11]heptacosa-6(11),7,9-triene-24-carboxamide
International Nonproprietary Names Click here for help
INN number INN
9219 vaniprevir
Synonyms Click here for help
analog 35b [PMID: 20163176] | MK-7009 | MK7009 | Vanihep®
Database Links Click here for help
BindingDB Ligand 103836
CAS Registry No. 923590-37-8 (source: PubChem)
ChEMBL Ligand CHEMBL4525964
DrugBank Ligand DB11929
GtoPdb PubChem SID 441604942
PubChem CID 24765256
RCSB PDB Ligand SU3
Search Google for chemical match using the InChIKey KUQWGLQLLVFLSM-ONAXAZCASA-N
Search Google for chemicals with the same backbone KUQWGLQLLVFLSM
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UniChem Compound Search for chemical match using the InChIKey KUQWGLQLLVFLSM-ONAXAZCASA-N
UniChem Connectivity Search for chemical match using the InChIKey KUQWGLQLLVFLSM-ONAXAZCASA-N