CHIR-99021   

GtoPdb Ligand ID: 8014

Synonyms: CHIR 99021 | CHIR99021 | CT-99021 | CT99021
Compound class: Synthetic organic
Comment: CHIR-99021 is an ATP-competitive inhibitor of glycogen synthase kinase-3α and β (GSK-3α/β), equipotent at both isozymes [5]. It was tested in preclinical studies.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 7
Hydrogen bond donors 3
Rotatable bonds 7
Topological polar surface area 115.2
Molecular weight 464.1
XLogP 4.16
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES N#Cc1ccc(nc1)NCCNc1ncc(c(n1)c1ccc(cc1Cl)Cl)c1ncc([nH]1)C
Isomeric SMILES N#Cc1ccc(nc1)NCCNc1ncc(c(n1)c1ccc(cc1Cl)Cl)c1ncc([nH]1)C
InChI InChI=1S/C22H18Cl2N8/c1-13-10-29-21(31-13)17-12-30-22(32-20(17)16-4-3-15(23)8-18(16)24)27-7-6-26-19-5-2-14(9-25)11-28-19/h2-5,8,10-12H,6-7H2,1H3,(H,26,28)(H,29,31)(H,27,30,32)
InChI Key AQGNHMOJWBZFQQ-UHFFFAOYSA-N
Bioactivity Comments
Oral administration of CHIR-99021 (30 mg/kg) increases glucose metabolism in a rodent model of type 2 diabetes [5]. In additional in vivo experiments, CHIR-99021 treatment improves glucose tolerance and reduces hyperglycemia [5].
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
glycogen synthase kinase 3 beta Hs Inhibitor Inhibition 8.2 pIC50 - 5
pIC50 8.2 (IC50 6.7x10-9 M) [5]
glycogen synthase kinase 3 alpha Hs Inhibitor Inhibition 8.0 pIC50 - 5
pIC50 8.0 (IC50 9.8x10-9 M) [5]
cyclin dependent kinase 1 Hs Inhibitor Inhibition 5.1 pIC50 - 5
pIC50 5.1 (IC50 8.8x10-6 M) [5]
mitogen-activated protein kinase 1 Hs Inhibitor Inhibition <5.0 pIC50 - 5
pIC50 <5.0 (IC50 >1x10-5 M) [5]