bosutinib   Click here for help

GtoPdb Ligand ID: 5710

Synonyms: Bosulif® | SK 606 | SK-606 | SKI 606
Approved drug PDB Ligand Immunopharmacology Ligand
bosutinib is an approved drug (FDA (2012), EMA (2013))
Compound class: Synthetic organic
Comment: Bosutinib is a Type-1 kinase inhibitor. This compound is a dual inhibitor of Src family kinases and Abl kinase activity [8].
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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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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 CDK toolkit. 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 1
Rotatable bonds 9
Topological polar surface area 82.88
Molecular weight 529.16
XLogP 3.63
No. Lipinski's rules broken 0
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.

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Canonical SMILES COc1cc2c(cc1OCCCN1CCN(CC1)C)ncc(c2Nc1cc(OC)c(cc1Cl)Cl)C#N
Isomeric SMILES COc1cc2c(cc1OCCCN1CCN(CC1)C)ncc(c2Nc1cc(OC)c(cc1Cl)Cl)C#N
InChI InChI=1S/C26H29Cl2N5O3/c1-32-6-8-33(9-7-32)5-4-10-36-25-13-21-18(11-24(25)35-3)26(17(15-29)16-30-21)31-22-14-23(34-2)20(28)12-19(22)27/h11-14,16H,4-10H2,1-3H3,(H,30,31)
InChI Key UBPYILGKFZZVDX-UHFFFAOYSA-N
Bioactivity Comments
A large set of screening data for bosutinib is reported by Remsing et al (2009) [9]. This provides a range of kinases where bosutinib is active, in addition to its originally reported molecular kinase targets. Two of the newly identified target families are the TEC and STK20 kinase families and in addition, this is the first report of a compound able to inhibit kinase activity of calcium/calmodulin-dependent protein kinase II gamma subunit (CAMK2G). It is suggested by the authors that inhibition of this latter enzyme may be partially responsible for bosutinib's beneficial effect in chronic myeloid leukemia (CML). This data set was produced from cellular growth-inhibition assays in vitro and from biochemical kinase assays.
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
mitogen-activated protein kinase kinase kinase kinase 5 Hs Inhibitor Inhibition 9.5 pIC50 - 9
⤷ pIC50 9.5 (IC50 3x10-10 M) [9]
TXK tyrosine kinase Hs Inhibitor Inhibition 9.5 pIC50 - 9
⤷ pIC50 9.5 (IC50 3x10-10 M) [9]
ABL proto-oncogene 1, non-receptor tyrosine kinase Primary target of this compound Hs Inhibitor Inhibition 9.0 pIC50 - 6
⤷ pIC50 9.0 (IC50 1x10-9 M) [6]
SRC proto-oncogene, non-receptor tyrosine kinase Hs Inhibitor Inhibition 9.0 pIC50 - 2
⤷ pIC50 9.0 (IC50 1x10-9 M) [2]
FYN proto-oncogene, Src family tyrosine kinase Hs Inhibitor Inhibition 8.7 pIC50 - 9
⤷ pIC50 8.7 (IC50 1.8x10-9 M) [9]
fyn related Src family tyrosine kinase Hs Inhibitor Inhibition 8.7 pIC50 - 9
⤷ pIC50 8.7 (IC50 2.2x10-9 M) [9]
tyrosine kinase non receptor 2 Hs Inhibitor Inhibition 8.6 pIC50 - 9
⤷ pIC50 8.6 (IC50 2.7x10-9 M) [9]
salt inducible kinase 1 Hs Inhibitor Inhibition >8.5 pIC50 - 7
⤷ pIC50 >8.5 (IC50 <3x10-9 M) [7]
salt inducible kinase 2 Hs Inhibitor Inhibition >8.5 pIC50 - 7
⤷ pIC50 >8.5 (IC50 <3x10-9 M) [7]
serine/threonine kinase 24 Hs Inhibitor Inhibition 8.4 pIC50 - 9
⤷ pIC50 8.4 (IC50 3.9x10-9 M) [9]
LYN proto-oncogene, Src family tyrosine kinase Hs Inhibitor Inhibition 8.1 pIC50 - 9
⤷ pIC50 8.1 (IC50 8x10-9 M) [9]
SIK family kinase 3 Hs Inhibitor Inhibition 7.7 pIC50 - 7
⤷ pIC50 7.7 (IC50 1.8x10-8 M) [7]
serine/threonine kinase 10 Hs Inhibitor - 7.3 pIC50 - 9
⤷ pIC50 7.3 (IC50 5.2x10-8 M) [9]
calcium/calmodulin dependent protein kinase ID Hs Inhibitor Inhibition 7.0 pIC50 - 9
⤷ pIC50 7.0 (IC50 9.2x10-8 M) [9]
calcium/calmodulin-dependent protein kinase II gamma subunit Hs Inhibitor Inhibition 6.7 pIC50 - 9
⤷ pIC50 6.7 (IC50 1.84x10-7 M) [9]
serine/threonine kinase 4 Hs Inhibitor Inhibition 6.7 pIC50 - 9
⤷ pIC50 6.7 (IC50 1.91x10-7 M) [9]