obatoclax   Click here for help

GtoPdb Ligand ID: 11086

Synonyms: GX-15-070 | GX15-070 | obatoclax mesylate | SB16622
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Obatoclax is a small molecule inhibitor of Bcl-2 family proteins. Bcl-2 inhibition induces apoptosis in cancer cells [3-4,7]. We have matched the chemical structure to PubChem using the CAS number assigned in the WHO INN record for this drug, but note that various cis/trans isomers have been submitted to PubChem, and also thta the INN record does not in fact stipulate bond rotations. Enclosure of obatoclax in red blood-cell membrane-derived nanoparticles has been tested to overcome the compound's poor solubility [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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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 2
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 49.41
Molecular weight 317.15
XLogP 4.12
No. Lipinski's rules broken 0

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 COc1c/c(=C\2/C=c3c(=N2)cccc3)/[nH]/c/1=C\c1[nH]c(cc1C)C
Isomeric SMILES COc1c/c(=C\2/C=c3c(=N2)cccc3)/[nH]/c/1=C\c1[nH]c(cc1C)C
InChI InChI=1S/C20H19N3O/c1-12-8-13(2)21-16(12)10-19-20(24-3)11-18(23-19)17-9-14-6-4-5-7-15(14)22-17/h4-11,21,23H,1-3H3/b18-17+,19-10-
InChI Key CVCLJVVBHYOXDC-LKIBBAOUSA-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
Note that bioactivity may be assigned to the parent molecule or its mesylate salt.

Obatoclax is reported to rescue SARS-CoV-2 infected Vero-E6 cells from death, with an EC50 of 500 nM in a plaque assay [5].
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
BCL2 apoptosis regulator Hs Antagonist Antagonist 6.0 pKi - 9
⤷ pKi 6.0 (Ki 1.1x10-6 M) [9]
Description: In vitro antagonism determined in a fluorescence polarisation assay.
MCL1 apoptosis regulator, BCL2 family member Hs Antagonist Antagonist 5.5 pKi - 9
⤷ pKi 5.5 (Ki 2.9x10-6 M) [9]
Description: In vitro antagonism determined in a fluorescence polarisation assay.
Bcl-2-like 1 Hs Antagonist Antagonist 5.3 pKi - 9
⤷ pKi 5.3 (Ki 4.69x10-6 M) [9]
Description: In vitro antagonism determined in a fluorescence polarisation assay.