compound 25c [PMID: 23747811]   Click here for help

GtoPdb Ligand ID: 11641

Compound class: Peptide
Comment: Compound 25c was originally reported as an inhibitor of SARS-CoV 3CL protease (Mpro) [1]. It is virtually inactive against SARS-CoV-2 Mpro (IC50 >10 μM) [2].
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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.

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View interactive charts of activity data across species
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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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 CC(C[C@@H](C(=O)N[C@H](C(=O)c1nc2c(s1)cccc2)C[C@@H]1CCNC1=O)NC(=O)OCc1ccccc1)C
Isomeric SMILES CC(C[C@@H](C(=O)N[C@H](C(=O)c1nc2c(s1)cccc2)C[C@@H]1CCNC1=O)NC(=O)OCc1ccccc1)C
InChI InChI=1S/C28H32N4O5S/c1-17(2)14-22(32-28(36)37-16-18-8-4-3-5-9-18)26(35)30-21(15-19-12-13-29-25(19)34)24(33)27-31-20-10-6-7-11-23(20)38-27/h3-11,17,19,21-22H,12-16H2,1-2H3,(H,29,34)(H,30,35)(H,32,36)/t19-,21-,22-/m0/s1
InChI Key AJRQIXBBIDPNGK-BVSLBCMMSA-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. Thanigaimalai P, Konno S, Yamamoto T, Koiwai Y, Taguchi A, Takayama K, Yakushiji F, Akaji K, Kiso Y, Kawasaki Y et al.. (2013)
Design, synthesis, and biological evaluation of novel dipeptide-type SARS-CoV 3CL protease inhibitors: structure-activity relationship study.
Eur J Med Chem, 65: 436-47. [PMID:23747811]
2. Vankadara S, Wong YX, Liu B, See YY, Tan LH, Tan QW, Wang G, Karuna R, Guo X, Tan ST et al.. (2021)
A head-to-head comparison of the inhibitory activities of 15 peptidomimetic SARS-CoV-2 3CLpro inhibitors.
Bioorg Med Chem Lett, 48: 128263. [PMID:34271072]