dovitinib   Click here for help

GtoPdb Ligand ID: 5962

Synonyms: Chir 258 | CHIR-258 | TKI 258 | TKI-258
Compound class: Synthetic organic
Comment: Dovitinib is a multi-targeted receptor tyrosine kinase (RTK) inhibitor, with modest selectivity for Class III RTKs (IC50s 1-2nM), with IC50s for Class IV and V RTKs in the 8-13nM range. Please note that ChEMBL represents this compound as a tautomer of our structure.
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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

dovitinib 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 3
Rotatable bonds 1
Topological polar surface area 61.93
Molecular weight 392.18
XLogP 3.52
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 CN1CCN(CC1)c1ccc2c(c1)[nH]c(=C1C(=O)N=c3c(=C1N)c(F)ccc3)[nH]2
Isomeric SMILES CN1CCN(CC1)c1ccc2c(c1)[nH]/c(=C/1\C(=O)N=c3c(=C1N)c(F)ccc3)/[nH]2
InChI InChI=1S/C21H21FN6O/c1-27-7-9-28(10-8-27)12-5-6-14-16(11-12)25-20(24-14)18-19(23)17-13(22)3-2-4-15(17)26-21(18)29/h2-6,11,24-25H,7-10,23H2,1H3/b20-18-
InChI Key KCOYQXZDFIIGCY-ZZEZOPTASA-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
Dovitinib is a reversible ATP-competitive inhibitor of several receptor tyrosine kinases, including VEGFR-2, FGFR-1, and PDGFRβ [4]
Selectivity at catalytic receptors
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
fms related receptor tyrosine kinase 3 Primary target of this compound Hs Inhibitor Inhibition 9.2 pKd - 2
⤷ pKd 9.2 (Kd 6.4x10-10 M) [2]
fms related receptor tyrosine kinase 3 Primary target of this compound Hs Inhibitor Inhibition 8.5 – 9.0 pIC50 - 4-5
⤷ pIC50 8.5 – 9.0 (IC50 3x10-9 – 1x10-9 M) [4-5]
KIT proto-oncogene, receptor tyrosine kinase Hs Inhibitor Inhibition 8.5 – 8.7 pIC50 - 4-5
⤷ pIC50 8.5 – 8.7 (IC50 3x10-9 – 2x10-9 M) [4-5]
fms related receptor tyrosine kinase 4 Hs Inhibitor Inhibition 8.1 – 8.5 pIC50 - 4-5
⤷ pIC50 8.1 – 8.5 (IC50 8x10-9 – 3x10-9 M) [4-5]
fibroblast growth factor receptor 3 Hs Inhibitor Inhibition 8.1 – 8.5 pIC50 - 4-5
⤷ pIC50 8.1 – 8.5 (IC50 9x10-9 – 3x10-9 M) [4-5]
fms related receptor tyrosine kinase 1 Hs Inhibitor Inhibition 8.0 – 8.5 pIC50 - 4-5
⤷ pIC50 8.0 – 8.5 (IC50 1x10-8 – 3x10-9 M) [4-5]
fibroblast growth factor receptor 1 Hs Inhibitor Inhibition 8.0 – 8.1 pIC50 - 4-5
⤷ pIC50 8.0 – 8.1 (IC50 1.1x10-8 – 8x10-9 M) [4-5]
colony stimulating factor 1 receptor Hs Inhibitor Inhibition 7.4 – 8.5 pIC50 - 4-5
⤷ pIC50 7.4 – 8.5 (IC50 3.6x10-8 – 3x10-9 M) [4-5]
platelet derived growth factor receptor beta Hs Inhibitor Inhibition 7.6 – 8.3 pIC50 - 4-5
⤷ pIC50 7.6 – 8.3 (IC50 2.7x10-8 – 5x10-9 M) [4-5]
platelet derived growth factor receptor alpha Hs Inhibitor Inhibition 6.7 pIC50 - 5
⤷ pIC50 6.7 (IC50 2.1x10-7 M) [5]
epidermal growth factor receptor Hs Inhibitor Inhibition 5.7 pIC50 - 5
⤷ pIC50 5.7 (IC50 2x10-6 M) [5]
Insulin receptor Hs Inhibitor Inhibition 5.7 pIC50 - 5
⤷ pIC50 5.7 (IC50 2x10-6 M) [5]
kinase insert domain receptor Hs Inhibitor Inhibition - pIC50 - 4-5
⤷ pIC50 (IC50 6.5x10-8 – 1.3x10-8 M) [4-5]