1-azakenpaullone   Click here for help

GtoPdb Ligand ID: 8018

Synonyms: azakenpaullone
Compound class: Synthetic organic
Comment: 1-azakenpaullone is a potent and selective ATP-competitive inhibitor of glycogen synthase kinase-3β (GSK-3β) [4]. In contrast to other paullones, this analogue has insignificant activity at the phylogenetically related cyclin-dependent kinases (CDKs) CDK1 and CDK5. 1-azakenpaullone is compound 16 in [4].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 0
Topological polar surface area 57.78
Molecular weight 327
XLogP 2.6
No. Lipinski's rules broken 0
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Canonical SMILES O=C1Nc2cccnc2c2c(C1)c1cc(Br)ccc1[nH]2
Isomeric SMILES O=C1Nc2cccnc2c2c(C1)c1cc(Br)ccc1[nH]2
InChI InChI=1S/C15H10BrN3O/c16-8-3-4-11-9(6-8)10-7-13(20)18-12-2-1-5-17-15(12)14(10)19-11/h1-6,19H,7H2,(H,18,20)
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
glycogen synthase kinase 3 beta Primary target of this compound Hs Inhibitor Inhibition 7.7 pIC50 - 4
pIC50 7.7 (IC50 1.8x10-8 M) [4]
cyclin dependent kinase 1 Hs Inhibitor Inhibition 5.7 pIC50 - 4
pIC50 5.7 (IC50 2x10-6 M) [4]
Description: CDK1/cyclin B complex in assay
cyclin dependent kinase 5 Hs Inhibitor Inhibition 5.4 pIC50 - 4
pIC50 5.4 (IC50 4.2x10-6 M) [4]
Description: CDK5/p25 complex in assay