NARLAPREVIR

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Synonyms	Narlaprevir SCH 900518 SCH-900518
Status
Molecule Category	UNKNOWN
UNII	2857LA2O07


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	RICZEKWVNZFTNZ-LFGITCQGSA-N
Smiles	CCCC[C@H](NC(=O)[C@@H]1[C@@H]2[C@H](CN1C(=O)[C@@H](NC(=O)NC1(CS(=O)(=O)C(C)(C)C)CCCCC1)C(C)(C)C)C2(C)C)C(=O)C(=O)NC1CC1
InChI	InChI=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

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C36H61N5O7S
Molecular Weight	707.98
AlogP	3.62
Hydrogen Bond Acceptor	7.0
Hydrogen Bond Donor	4.0
Number of Rotational Bond	13.0
Polar Surface Area	170.85
Molecular species	NEUTRAL
Aromatic Rings	0.0
Heavy Atoms	49.0

Bioactivity

Mechanism of Action	Action	Reference
Hepatitis C virus serine protease, NS3/NS4A inhibitor	INHIBITOR	PubMed

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Protease Serine protease Serine protease PA clan Serine protease S29 family Serine protease S29 regulatory subfamily	-	-	-	6	-
Enzyme Protease Serine protease Serine protease PA clan Serine protease S29 family	-	-	-	6	-

Assay Description	Organism	Bioactivity	Reference
Inhibition of Hepatitis C virus genotype 3a NS3 protease	Hepatitis C virus subtype 3a	7.0 nM
Inhibition of Hepatitis C virus genotype 1a NS3 protease	Hepatitis C virus subtype 1a	0.7 nM
Inhibition of Hepatitis C virus genotype 2a NS3 protease	Hepatitis C virus subtype 2a	3.0 nM
Inhibition of Hepatitis C virus genotype 1b NS3 protease	Hepatitis C virus subtype 1b	7.0 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	7.98 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	-6.556 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.01 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.01 %
Inhibition of HCV NS3/4a protease using Ac-DE-Dap(QXL520)-EE-Abu-shi-[COO]AS-C(5-FAMsp)-NH2 as substrate after 15 mins	Hepatitis C virus	6.0 nM
Antiviral activity against HCV	Hepatitis C virus	40.0 nM

Cross References

Resources	Reference
ChEBI	173104
ChEMBL	CHEMBL1255891
FDA SRS	2857LA2O07
PubChem	11857239
SureChEMBL	SCHEMBL583183
ZINC	ZINC000068151111

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).