GSK583   

GtoPdb Ligand ID: 9134

Synonyms: GSK'583
Compound class: Synthetic organic
Comment: GSK583 is a potent and selective next generation inhibitor of receptor interacting serine/threonine kinase 2 (RIP2 kinase) [2]. It is compound 27 in [2] and compound 89 claimed in patent WO2011140442 [1]. GSK583 can be used as a tool compound to investigate the role played by RIP2 kinase in NOD1 and NOD2 mediated pathology.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 96.12
Molecular weight 398.12
XLogP 4.52
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES Fc1ccc2c(c1)c(n[nH]2)Nc1ccnc2c1cc(cc2)S(=O)(=O)C(C)(C)C
Isomeric SMILES Fc1ccc2c(c1)c(n[nH]2)Nc1ccnc2c1cc(cc2)S(=O)(=O)C(C)(C)C
InChI InChI=1S/C20H19FN4O2S/c1-20(2,3)28(26,27)13-5-7-16-14(11-13)17(8-9-22-16)23-19-15-10-12(21)4-6-18(15)24-25-19/h4-11H,1-3H3,(H2,22,23,24,25)
InChI Key XLOGLWKOHPIJLV-UHFFFAOYSA-N
Bioactivity Comments
A kinome scan shows that at 1µM GSK583 is selective for RIP2 kinase in the panel of 300 kinases tested [2]. GSK583 is effective in cellular asays assessing its ability to inhibit pro-inflammatory cytokine release in response to NOD2 pathway actvation by muramyldipeptide (MDP).
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
receptor interacting serine/threonine kinase 2 Rn Inhibitor Inhibition 8.7 pIC50 - 2
pIC50 8.7 (IC50 2x10-9 M) [2]
receptor interacting serine/threonine kinase 2 Hs Inhibitor Inhibition 8.3 pIC50 - 2
pIC50 8.3 (IC50 5x10-9 M) [2]