calpeptin   Click here for help

GtoPdb Ligand ID: 11643

Synonyms: benzylcarbonyl-Leu-nLeu-H | N-benzyloxycarbonyl-L-leucyl-L-norleucinal
Compound class: Peptide
Comment: Calpeptin is a dipeptidyl inhibitor of calpain cysteine proteases.
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species

calpeptin is commercially available from our sponsors

2D Structure
Click here for help

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.

✖
Click here for structure editor
SMILES / InChI / InChIKey
Click here for help

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/)

✖
Canonical SMILES CCCC[C@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)CC(C)C)C=O
Isomeric SMILES CCCC[C@@H](C=O)NC(=O)[C@H](CC(C)C)NC(=O)OCc1ccccc1
InChI InChI=1S/C20H30N2O4/c1-4-5-11-17(13-23)21-19(24)18(12-15(2)3)22-20(25)26-14-16-9-7-6-8-10-16/h6-10,13,15,17-18H,4-5,11-12,14H2,1-3H3,(H,21,24)(H,22,25)/t17-,18-/m0/s1
InChI Key PGGUOGKHUUUWAF-ROUUACIJSA-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/)
References
1. Catalano JG, Deaton DN, Long ST, McFadyen RB, Miller LR, Payne JA, Wells-Knecht KJ, Wright LL. (2004)
Design of small molecule ketoamide-based inhibitors of cathepsin K.
Bioorg Med Chem Lett, 14 (3): 719-22. [PMID:14741275]
2. Iqbal M, Messina PA, Freed B, Das M, Chatterjee S, Tripathy R, Ming Tao, Josef KA, Dembofsky B, Dunn D et al.. (1997)
Subsite requirements for peptide aldehyde inhibitors of human calpain I.
Bioorg Med Chem Lett, 7: 539-544. DOI: 10.1016/S0960-894X(97)00063-2
3. Ma C, Sacco MD, Hurst B, Townsend JA, Hu Y, Szeto T, Zhang X, Tarbet B, Marty MT, Chen Y et al.. (2020)
Boceprevir, GC-376, and calpain inhibitors II, XII inhibit SARS-CoV-2 viral replication by targeting the viral main protease.
Cell Res, 30 (8): 678-692. DOI: 10.1038/s41422-020-0356-z [PMID:32541865]