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
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (Japan 2014)
IUPAC Name Click here for help
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
Search Google for chemical match using the InChIKey KUQWGLQLLVFLSM-ONAXAZCASA-N
Search Google for chemicals with the same backbone KUQWGLQLLVFLSM
Search PubMed clinical trials vaniprevir
Search PubMed titles vaniprevir
Search PubMed titles/abstracts vaniprevir
UniChem Compound Search for chemical match using the InChIKey KUQWGLQLLVFLSM-ONAXAZCASA-N
UniChem Connectivity Search for chemical match using the InChIKey KUQWGLQLLVFLSM-ONAXAZCASA-N