vodobatinib   Click here for help

GtoPdb Ligand ID: 11191

Synonyms: SCO-088 | SCO088 | SUN-K706 | SUNK706
Compound class: Synthetic organic
Comment: The chemical structure submitted to the WHO for the INN vodobatinib is identical to that of Sun Pharma's Bcr-Abl1 inhibitor SCO-088 (SUN-K706, or simply K0706), via a PubChem structure match. SCO-088 is a third generation Bcr-Abl1 tyrosine kinase inhibitor that was developed to combat treatment resistant chronic myeloid leukemia (CML) [1].
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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

vodobatinib 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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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 5
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 71.09
Molecular weight 453.12
XLogP 7.22
No. Lipinski's rules broken 1

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 O=C(c1ccc(c(c1)C#Cc1cnc2c(c1)cccc2)C)NNC(=O)c1c(C)cccc1Cl
Isomeric SMILES O=C(c1ccc(c(c1)C#Cc1cnc2c(c1)cccc2)C)NNC(=O)c1c(C)cccc1Cl
InChI InChI=1S/C27H20ClN3O2/c1-17-10-12-22(26(32)30-31-27(33)25-18(2)6-5-8-23(25)28)15-20(17)13-11-19-14-21-7-3-4-9-24(21)29-16-19/h3-10,12,14-16H,1-2H3,(H,30,32)(H,31,33)
InChI Key ZQOBVMHBVWNVBG-UHFFFAOYSA-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
K0706 inhibits a range of clinically relevant BCR-ABL1 point mutants, but does not inhibit BCR-ABL1T315I [1].
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
ABL proto-oncogene 1, non-receptor tyrosine kinase Hs Inhibitor Inhibition 6.8 – 8.2 pIC50 - 1
⤷ pIC50 8.2 (IC50 6x10-9 M) [1]
Description: Inhibition of Abl1F311L expressed in in Ba/F3 cells.
pIC50 8.1 (IC50 7x10-9 M) [1]
Description: Inhibition of wild type Abl1 expressed in in Ba/F3 cells.
pIC50 6.8 (IC50 1.65x10-7 M) [1]
Description: Inhibition of Abl1E255V expressed in in Ba/F3 cells.