compound 4g [PMID: 21316219]   

GtoPdb Ligand ID: 8211

Compound class: Synthetic organic
Comment: Compound 4g is an alkoxy derivative of compound 4a [1] and was reported in a medicinal chemistry/structure aided design study to identify improved inhibitors of interleukin-2 inducible T-cell kinase (ITK).
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 74.43
Molecular weight 352.13
XLogP 4.42
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES O=C(c1ccccc1)Cc1ccc2c(c1)[nH]c(c2)c1n[nH]c2c1nccc2
Isomeric SMILES O=C(c1ccccc1)Cc1ccc2c(c1)[nH]c(c2)c1n[nH]c2c1nccc2
InChI InChI=1S/C22H16N4O/c27-20(15-5-2-1-3-6-15)12-14-8-9-16-13-19(24-18(16)11-14)22-21-17(25-26-22)7-4-10-23-21/h1-11,13,24H,12H2,(H,25,26)
InChI Key CDVMXMZPDJHSCC-UHFFFAOYSA-N
Bioactivity Comments
0.1μM of compound 4g inhibits seven kinases (out of a selectivity profiling set of 108) by >80%, inhibiting ITK by 79% in this screen [1]. These off-targets are RSK1, TrkA, PIM1, FLT3, RET, JAK2 and Aurora kinase A. KDR is inhibited by 75% in the same assay [1].
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
IL2 inducible T cell kinase Hs Inhibitor Inhibition 7.2 pIC50 - 1
pIC50 7.2 (IC50 6x10-8 M) [1]