narlaprevir   Click here for help

GtoPdb Ligand ID: 11572

Synonyms: Arlansa® | SCH 900518 | SCH-900518 | SCH900518
Approved drug
narlaprevir is an approved drug (Russia (2016))
Compound class: Synthetic organic
Comment: Narlaprevir (SCH90051) is an oral HCV NS3 serine protease inhibitor [1,3]. It is structurally related to boceprevir. Narlaprevir forms a reversible covalent bond with the protease's active-site serine. It has also been reported to inhibit SARS-CoV-2 coronavirus main cysteine protease (3CLpro or Mpro) in vitro [2].

narlaprevir is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 12
Hydrogen bond donors 4
Rotatable bonds 20
Topological polar surface area 179.23
Molecular weight 707.43
XLogP 5.97
No. Lipinski's rules broken 3

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. Russia (2016)
IUPAC Name Click here for help
narlaprevir
International Nonproprietary Names Click here for help
INN number INN
9227 narlaprevir
Synonyms Click here for help
Arlansa® | SCH 900518 | SCH-900518 | SCH900518
Database Links Click here for help
CAS Registry No. 865466-24-6 (source: PubChem)
ChEMBL Ligand CHEMBL1255891
GtoPdb PubChem SID 441604944
PubChem CID 11857239
Search Google for chemical match using the InChIKey RICZEKWVNZFTNZ-LFGITCQGSA-N
Search Google for chemicals with the same backbone RICZEKWVNZFTNZ
Search PubMed clinical trials narlaprevir
Search PubMed titles narlaprevir
Search PubMed titles/abstracts narlaprevir
UniChem Compound Search for chemical match using the InChIKey RICZEKWVNZFTNZ-LFGITCQGSA-N
UniChem Connectivity Search for chemical match using the InChIKey RICZEKWVNZFTNZ-LFGITCQGSA-N

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MedChemExpress
Narlaprevir (links to external site)
Cat. No. HY-10300