boceprevir   Click here for help

GtoPdb Ligand ID: 7876

Synonyms: EBP-520 | EBP520 | SCH-503034 | SCH503034 | Victrelis®
Approved drug
boceprevir is an approved drug (EMA & FDA (2011))
Compound class: Synthetic organic
Comment: Boceprevir is an active site-binding inhibitor of the main protease (nonstructural protein 3, NS3) of hepatitis C virus (HCV). A patent claims boceprevir for repurposing as cathepsin A modulator [3]. More recently it has been reported to inhibit the 3CL protease (Mpro) of several coronaviruses, including SARS-CoV-2 Mpro [1]. An alternative enantiomer is reported in the SARS-CoV-2 Mpro/boceprevir crystal structure 6WNP, which maps to PubChem CID 71316139.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 10
Hydrogen bond donors 4
Rotatable bonds 14
Topological polar surface area 150.7
Molecular weight 519.34
XLogP 2.83
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES O=C(NC(C)(C)C)NC(C(C)(C)C)C(=O)N1CC2C(C1C(=O)NC(C(=O)C(=O)N)CC1CCC1)C2(C)C
Isomeric SMILES O=C(NC(C)(C)C)N[C@@H](C(C)(C)C)C(=O)N1C[C@H]2[C@@H]([C@H]1C(=O)NC(C(=O)C(=O)N)CC1CCC1)C2(C)C
InChI InChI=1S/C27H45N5O5/c1-25(2,3)20(30-24(37)31-26(4,5)6)23(36)32-13-15-17(27(15,7)8)18(32)22(35)29-16(19(33)21(28)34)12-14-10-9-11-14/h14-18,20H,9-13H2,1-8H3,(H2,28,34)(H,29,35)(H2,30,31,37)/t15-,16?,17-,18-,20+/m0/s1
InChI Key LHHCSNFAOIFYRV-DOVBMPENSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (EMA & FDA (2011))
Withdrawn drug? Yes
IUPAC Name Click here for help
(1R,2S,5S)-N-(4-amino-1-cyclobutyl-3,4-dioxobutan-2-yl)-3-[(2S)-2-(tert-butylcarbamoylamino)-3,3-dimethylbutanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide
International Nonproprietary Names Click here for help
INN number INN
8840 boceprevir
Synonyms Click here for help
EBP-520 | EBP520 | SCH-503034 | SCH503034 | Victrelis®
Database Links Click here for help
CAS Registry No. 394730-60-0 (source: Scifinder)
ChEBI CHEBI:68621
ChEMBL Ligand CHEMBL218394
DrugBank Ligand DB05665
DrugCentral Ligand 4172
GtoPdb PubChem SID 223366205
PubChem CID 10324367
Search Google for chemical match using the InChIKey LHHCSNFAOIFYRV-DOVBMPENSA-N
Search Google for chemicals with the same backbone LHHCSNFAOIFYRV
Search PubMed clinical trials boceprevir
Search PubMed titles boceprevir
Search PubMed titles/abstracts boceprevir
Search UniChem for chemical match using the InChIKey LHHCSNFAOIFYRV-DOVBMPENSA-N
Search UniChem for chemicals with the same backbone LHHCSNFAOIFYRV
Wikipedia Boceprevir