SP600125   Click here for help

GtoPdb Ligand ID: 5273

Synonyms: 1,9-pyrazoloanthrone | JNK Inhibitor II | SP-600125
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: SP600125 is an ATP-competitive, pan JNK inhibitor with potent activity against JNK1, JNK2 and JNK3 [2]. Off targets including the aryl hydrocarbon receptor (AhR; agonist) [5], Mps1 (TTK, a tyrosine, serine and threonine kinase) [6], and some serine/threonine kinases (Aurora kinase A, FLT3, MELK, and TRKA) [3] have been identified.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 0
Topological polar surface area 45.75
Molecular weight 220.06
XLogP 4.1
No. Lipinski's rules broken 0
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Canonical SMILES O=c1c2ccccc2c2c3c1cccc3[nH]n2
Isomeric SMILES O=c1c2ccccc2c2c3c1cccc3[nH]n2
InChI InChI=1S/C14H8N2O/c17-14-9-5-2-1-4-8(9)13-12-10(14)6-3-7-11(12)15-16-13/h1-7H,(H,15,16)
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. Bennett BL, Sasaki DT, Murray BW, O'Leary EC, Sakata ST, Xu W, Leisten JC, Motiwala A, Pierce S, Satoh Y et al.. (2001)
SP600125, an anthrapyrazolone inhibitor of Jun N-terminal kinase.
Proc Natl Acad Sci USA, 98 (24): 13681-6. [PMID:11717429]
3. Colombo R, Caldarelli M, Mennecozzi M, Giorgini ML, Sola F, Cappella P, Perrera C, Depaolini SR, Rusconi L, Cucchi U et al.. (2010)
Targeting the mitotic checkpoint for cancer therapy with NMS-P715, an inhibitor of MPS1 kinase.
Cancer Res, 70 (24): 10255-64. [PMID:21159646]
4. 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]
5. Joiakim A, Mathieu PA, Palermo C, Gasiewicz TA, Reiners Jr JJ. (2003)
The Jun N-terminal kinase inhibitor SP600125 is a ligand and antagonist of the aryl hydrocarbon receptor.
Drug Metab Dispos, 31 (11): 1279-82. [PMID:14570754]
6. Schmidt M, Budirahardja Y, Klompmaker R, Medema RH. (2005)
Ablation of the spindle assembly checkpoint by a compound targeting Mps1.
EMBO Rep, 6 (9): 866-72. [PMID:16113653]