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CHEBI:173104 - narlaprevir

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.
anticoronaviral agent  Any antiviral agent which inhibits the activity of coronaviruses.
hepatitis C protease inhibitor  An inhibitor of hepatitis C protease, an enzyme required for production of proteins needed for viral assembly.
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
narlaprévirWHO MedNet
narlaprevirumWHO MedNet
narlaprevirWHO MedNet
narlaprevirWHO MedNet
Synonyms  Source
SCH 900518ChemIDplus
(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
(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
SCH900518ChemIDplus
SCH-900518ChemIDplus
Brand Name  Source
ArlansaChEBI
Manual XrefsDatabases
NarlaprevirWikipedia
NNAPDBeChem
DB14760DrugBank
D09644KEGG DRUG
LSM-45473LINCS
10031710ChemSpider
Registry NumbersSources
CAS:865466-24-6ChemIDplus
Citations