GSK-3beta inhibitor VIII   Click here for help

GtoPdb Ligand ID: 5979

Synonyms: AR-A014418 | GSK-3b inhibitor VIII
PDB Ligand
Compound class: Synthetic organic
Comment: This is an experimental cell-permeable, ATP-competitive inhibitor of glycogen synthase kinase-3β (GSK-3β) [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 134.63
Molecular weight 308.06
XLogP 1
No. Lipinski's rules broken 0
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Canonical SMILES COc1ccc(cc1)CNC(=O)Nc1ncc(s1)[N+](=O)[O-]
Isomeric SMILES COc1ccc(cc1)CNC(=O)Nc1ncc(s1)[N+](=O)[O-]
InChI InChI=1S/C12H12N4O4S/c1-20-9-4-2-8(3-5-9)6-13-11(17)15-12-14-7-10(21-12)16(18)19/h2-5,7H,6H2,1H3,(H2,13,14,15,17)
Bioactivity Comments
In a mouse model of amyotrophic lateral sclerosis (ALS) treatment with this compound delays the onset of symptoms, improves motor activity and slows down progression of the disease, delaying terminal disease state [7]. These results confirm the role of GSK-3β in a neurodegenerative disease other than Alzheimer's disease. This compound does not significantly inhibit CDK2 or CDK5 which are phylogenetic close relatives of GSK-3 [2].
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 7.4 pKi - 2
pKi 7.4 (Ki 3.8x10-8 M) [2]