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
References
1. Bury JM et al.. (2011)
Amino-quinolines as kinase inhibitors.
Patent number: WO2011140442 A1. Assignee: Glaxo Group Limited. Priority date: 07/05/2010. Publication date: 10/11/2011.
2. Haile PA, Votta BJ, Marquis RW, Bury MJ, Mehlmann JF, Singhaus Jr R, Charnley AK, Lakdawala AS, Convery MA, Lipshutz DB et al.. (2016)
The Identification and Pharmacological Characterization of 6-(tert-Butylsulfonyl)-N-(5-fluoro-1H-indazol-3-yl)quinolin-4-amine (GSK583), a Highly Potent and Selective Inhibitor of RIP2 Kinase.
J. Med. Chem., 59 (10): 4867-80. [PMID:27109867]