MG-132   Click here for help

GtoPdb Ligand ID: 8616

Synonyms: compound 5b [PMID: 16686537] | MG132 | N-benzyloxycarbonyl-L-leucyl-L-leucyl-L-leucinal | Z-Leu-leu-leu-al | Z-LLL-CHO
PDB Ligand
Compound class: Peptide
Comment: Compound 5b is reported to inhibit the enzymatic activity of proteasome macropain [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

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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 O=CC(NC(=O)C(NC(=O)C(NC(=O)OCc1ccccc1)CC(C)C)CC(C)C)CC(C)C
Isomeric SMILES O=C[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)CC(C)C)CC(C)C)CC(C)C
InChI InChI=1S/C26H41N3O5/c1-17(2)12-21(15-30)27-24(31)22(13-18(3)4)28-25(32)23(14-19(5)6)29-26(33)34-16-20-10-8-7-9-11-20/h7-11,15,17-19,21-23H,12-14,16H2,1-6H3,(H,27,31)(H,28,32)(H,29,33)/t21-,22-,23-/m0/s1
InChI Key TZYWCYJVHRLUCT-VABKMULXSA-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/)
Bioactivity Comments
Compound 5b also inhibits cathepsin B activity with a Ki of 12nM. In vitro, compound 5b inhibits growth of human prostate PC3 tumour cells [2]. We have mapped this compound to the β5 macropain subunit, as this is the subunit commented on by Rydzewski et al. (2006) [2].
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
proteasome 20S subunit beta 5 Hs Inhibitor Inhibition 8.4 pKi - 2
⤷ pKi 8.4 (Ki 3.7x10-9 M) [2]
Description: Inhibition of the chymotrypsin-like activity of proteasome macropain.
proteasome 20S subunit beta 2 N/A Inhibitor Inhibition 6.5 pKi - 2
⤷ pKi 6.5 (Ki 3x10-7 M) [2]
Selectivity at other protein targets
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
CoV 3C-like (main) protease SARS-CoV-2 Inhibitor Inhibition 5.4 pIC50 - 1
⤷ pIC50 5.4 (IC50 3.9x10-6 M) [1]