SB203580   Click here for help

GtoPdb Ligand ID: 5269

Synonyms: PB 203580 | RWJ 64809 | SB-203580
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: SB203580 inhibits p38 MAPK enzymes, with some selectivity for p38α. The compound has been used to dissect the p38 signalling pathway and to determine the binding mode and differentiate functions between the four p38 MAP kinase homologues [4,6]. The hydrochloride salt is water-soluble.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 77.85
Molecular weight 377.1
XLogP 3.75
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES Fc1ccc(cc1)c1nc([nH]c1c1ccncc1)c1ccc(cc1)S(=O)C
Isomeric SMILES Fc1ccc(cc1)c1nc([nH]c1c1ccncc1)c1ccc(cc1)S(=O)C
InChI InChI=1S/C21H16FN3OS/c1-27(26)18-8-4-16(5-9-18)21-24-19(14-2-6-17(22)7-3-14)20(25-21)15-10-12-23-13-11-15/h2-13H,1H3,(H,24,25)
InChI Key CDMGBJANTYXAIV-UHFFFAOYSA-N
References
1. Anastassiadis T, Deacon SW, Devarajan K, Ma H, Peterson JR. (2011)
Comprehensive assay of kinase catalytic activity reveals features of kinase inhibitor selectivity.
Nat Biotechnol, 29 (11): 1039-45. [PMID:22037377]
2. Davis MI, Hunt JP, Herrgard S, Ciceri P, Wodicka LM, Pallares G, Hocker M, Treiber DK, Zarrinkar PP. (2011)
Comprehensive analysis of kinase inhibitor selectivity.
Nat Biotechnol, 29 (11): 1046-51. [PMID:22037378]
3. Eyers PA, Craxton M, Morrice N, Cohen P, Goedert M. (1998)
Conversion of SB 203580-insensitive MAP kinase family members to drug-sensitive forms by a single amino-acid substitution.
Chem Biol, 5 (6): 321-8. [PMID:9653550]
4. Frantz B, Klatt T, Pang M, Parsons J, Rolando A, Williams H, Tocci MJ, O'Keefe SJ, O'Neill EA. (1998)
The activation state of p38 mitogen-activated protein kinase determines the efficiency of ATP competition for pyridinylimidazole inhibitor binding.
Biochemistry, 37 (39): 13846-53. [PMID:9753474]
5. Gao Y, Davies SP, Augustin M, Woodward A, Patel UA, Kovelman R, Harvey KJ. (2013)
A broad activity screen in support of a chemogenomic map for kinase signalling research and drug discovery.
Biochem J, 451 (2): 313-28. [PMID:23398362]
6. Lee JC, Kumar S, Griswold DE, Underwood DC, Votta BJ, Adams JL. (2000)
Inhibition of p38 MAP kinase as a therapeutic strategy.
Immunopharmacology, 47 (2-3): 185-201. [PMID:10878289]
7. Wodicka LM, Ciceri P, Davis MI, Hunt JP, Floyd M, Salerno S, Hua XH, Ford JM, Armstrong RC, Zarrinkar PP et al.. (2010)
Activation state-dependent binding of small molecule kinase inhibitors: structural insights from biochemistry.
Chem Biol, 17 (11): 1241-9. [PMID:21095574]