ibrutinib   Click here for help

GtoPdb Ligand ID: 6912

Synonyms: Imbruvica® | PCI-32765
Approved drug PDB Ligand Immunopharmacology Ligand
ibrutinib is an approved drug (FDA (2013), EMA (2014))
Compound class: Synthetic organic
Comment: Ibrutinib is a clinically used inhibitor of Bruton's tyrosine kinase. It was originally approved with breakthrough therapy designation through the FDA's accelerated approval program.
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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 6
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 99.16
Molecular weight 440.2
XLogP 4.12
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 C=CC(=O)N1CCCC(C1)n1nc(c2c1ncnc2N)c1ccc(cc1)Oc1ccccc1
Isomeric SMILES C=CC(=O)N1CCC[C@H](C1)n1nc(c2c1ncnc2N)c1ccc(cc1)Oc1ccccc1
InChI InChI=1S/C25H24N6O2/c1-2-21(32)30-14-6-7-18(15-30)31-25-22(24(26)27-16-28-25)23(29-31)17-10-12-20(13-11-17)33-19-8-4-3-5-9-19/h2-5,8-13,16,18H,1,6-7,14-15H2,(H2,26,27,28)/t18-/m1/s1
InChI Key XYFPWWZEPKGCCK-GOSISDBHSA-N
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
BLK proto-oncogene, Src family tyrosine kinase Hs Inhibitor Inhibition 9.3 – 10.0 pIC50 - 2-3
⤷ pIC50 10.0 (IC50 1x10-10 M) [2]
pIC50 9.3 (IC50 5x10-10 M) [3]
BMX non-receptor tyrosine kinase Hs Inhibitor Inhibition 9.1 pIC50 - 2-3
⤷ pIC50 9.1 (IC50 8x10-10 M) [3]
pIC50 9.1 (IC50 8x10-10 M) [2]
Bruton tyrosine kinase Primary target of this compound Hs Inhibitor Inhibition 8.8 – 9.3 pIC50 - 2,4
⤷ pIC50 9.3 (IC50 5x10-10 M) [4]
pIC50 8.8 (IC50 1.5x10-9 M) [2]
TXK tyrosine kinase Hs Inhibitor Inhibition 8.7 pIC50 - 2
⤷ pIC50 8.7 (IC50 2x10-9 M) [2]
YES proto-oncogene 1, Src family tyrosine kinase Hs Inhibitor Inhibition 8.4 pIC50 - 2
⤷ pIC50 8.4 (IC50 4.1x10-9 M) [2]
IL2 inducible T cell kinase Hs Inhibitor Inhibition 8.3 pIC50 - 2
⤷ pIC50 8.3 (IC50 4.9x10-9 M) [2]
LCK proto-oncogene, Src family tyrosine kinase Hs Inhibitor Inhibition 8.2 pIC50 - 2
⤷ pIC50 8.2 (IC50 6.3x10-9 M) [2]
tec protein tyrosine kinase Hs Inhibitor Inhibition 8.1 pIC50 - 2
⤷ pIC50 8.1 (IC50 7x10-9 M) [2]
SRC proto-oncogene, non-receptor tyrosine kinase Hs Inhibitor Inhibition 7.7 pIC50 - 2
⤷ pIC50 7.7 (IC50 1.9x10-8 M) [2]
LYN proto-oncogene, Src family tyrosine kinase Hs Inhibitor Inhibition 7.7 pIC50 - 2
⤷ pIC50 7.7 (IC50 2x10-8 M) [2]
FYN proto-oncogene, Src family tyrosine kinase Hs Inhibitor Inhibition 7.5 pIC50 - 2
⤷ pIC50 7.5 (IC50 2.9x10-8 M) [2]
HCK proto-oncogene, Src family tyrosine kinase Hs Inhibitor Inhibition 7.5 pIC50 - 2
⤷ pIC50 7.5 (IC50 2.9x10-8 M) [2]
Janus kinase 3 Hs Inhibitor Inhibition 7.5 pIC50 - 2
⤷ pIC50 7.5 (IC50 3.2x10-8 M) [2]
Selectivity at catalytic receptors
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
erb-b2 receptor tyrosine kinase 4 Hs Inhibitor Inhibition 8.5 pIC50 - 2
⤷ pIC50 8.5 (IC50 3.4x10-9 M) [2]
epidermal growth factor receptor Hs Inhibitor Inhibition 8.3 pIC50 - 2
⤷ pIC50 8.3 (IC50 5.3x10-9 M) [2]
erb-b2 receptor tyrosine kinase 2 Hs Inhibitor Inhibition 8.2 pIC50 - 2
⤷ pIC50 8.2 (IC50 6.4x10-9 M) [2]