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CHEBI:173104 - narlaprevir

Default Structure
ChEBI IDCHEBI:173104
ChEBI Namenarlaprevir
Stars
DefinitionAn azabicyclohexane that is (1R,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane substituted by [(3S)-1-(cyclopropylamino)-1,2-dioxoheptan-3-yl]aminoacyl and N-({1-[(tert-butylsulfonyl)methyl]cyclohexyl}carbamoyl)-3-methyl-L-valyl groups at positions 2S and 3, respectively. It is a hepatitis C virus (HCV) NS3/4A serine protease inhibitor (Ki = 6 nM) that is used for the treatment of chronic hepatitis C.
Last Modified28 May 2021
SubmitterR. Stephan
DownloadsMolfile
FormulaC36H61N5O7S
Net Charge0
Average Mass707.979
Monoisotopic Mass707.42917
SMILES[H][C@@]12[C@@H](C(=O)N[C@@H](CCCC)C(=O)C(=O)NC3CC3)N(C(=O)[C@@H](NC(=O)NC3(CS(=O)(=O)C(C)(C)C)CCCCC3)C(C)(C)C)C[C@]1([H])C2(C)C
InChIInChI=1S/C36H61N5O7S/c1-10-11-15-24(27(42)30(44)37-22-16-17-22)38-29(43)26-25-23(35(25,8)9)20-41(26)31(45)28(33(2,3)4)39-32(46)40-36(18-13-12-14-19-36)21-49(47,48)34(5,6)7/h22-26,28H,10-21H2,1-9H3,(H,37,44)(H,38,43)(H2,39,40,46)/t23-,24-,25-,26-,28+/m0/s1
InChIKeyRICZEKWVNZFTNZ-LFGITCQGSA-N
Wikipedia
Roles Classification
Biological Roles:
antiviral drug  A substance used in the prophylaxis or therapy of virus diseases.
hepatitis C protease inhibitor  An inhibitor of hepatitis C protease, an enzyme required for production of proteins needed for viral assembly.
anticoronaviral agent  Any antiviral agent which inhibits the activity of coronaviruses.
EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor  An EC 3.4.22.* (cysteine endopeptidase) inhibitor that interferes with the action of SARS coronavirus main proteinase (EC 3.4.22.69).
Application:
antiviral drug  A substance used in the prophylaxis or therapy of virus diseases.
ChEBI Ontology
Outgoing Relation(s)
narlaprevir (CHEBI:173104) has role anticoronaviral agent (CHEBI:149553)
narlaprevir (CHEBI:173104) has role antiviral drug (CHEBI:36044)
narlaprevir (CHEBI:173104) has role EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor (CHEBI:147285)
narlaprevir (CHEBI:173104) has role hepatitis C protease inhibitor (CHEBI:64924)
narlaprevir (CHEBI:173104) is a azabicyclohexane (CHEBI:170008)
narlaprevir (CHEBI:173104) is a cyclopropanes (CHEBI:51454)
narlaprevir (CHEBI:173104) is a pyrrolidinecarboxamide (CHEBI:46770)
narlaprevir (CHEBI:173104) is a secondary carboxamide (CHEBI:140325)
narlaprevir (CHEBI:173104) is a sulfone (CHEBI:35850)
narlaprevir (CHEBI:173104) is a tertiary carboxamide (CHEBI:140326)
narlaprevir (CHEBI:173104) is a ureas (CHEBI:47857)
IUPAC Name 
(1R,2S,5S)-3-[N-({1-[(tert-butylsulfonyl)methyl]cyclohexyl}carbamoyl)-3-methyl-L-valyl]-N-[(3S)-1-(cyclopropylamino)-1,2-dioxoheptan-3-yl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide
INNs  Source
narlaprevirWHO MedNet
narlaprevirWHO MedNet
narlaprévirWHO MedNet
narlaprevirumWHO MedNet
Synonyms  Source
(1R,2S,5S)-3-{(2S)-2-[({1-[(tert-butylsulfonyl)methyl]cyclohexyl}carbamoyl)amino]-3,3-dimethylbutanoyl}-N-[(3S)-1-(cyclopropylamino)-1,2-dioxoheptan-3-yl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamideIUPAC
(1R,2S,5S)-N-[(3S)-1-(cyclopropylamino)-1,2-dioxoheptan-3-yl]-6,6-dimethyl-3-[3-methyl-N-({1-[(2-methylpropane-2-sulfonyl)methyl]cyclohexyl}carbamoyl)-L-valyl]-3-azabicyclo[3.1.0]hexane-2-carboxamideIUPAC
SCH 900518ChemIDplus
SCH-900518ChemIDplus
SCH900518ChemIDplus
Brand Name  Source
ArlansaChEBI
Manual XrefsDatabases
10031710ChemSpider
D09644KEGG DRUG
DB14760DrugBank
LSM-45473LINCS
NarlaprevirWikipedia
NNAPDBeChem
Registry NumbersSources
CAS:865466-24-6ChemIDplus
Citations