SU9516   Click here for help

GtoPdb Ligand ID: 6045

Synonyms: AC1NRD9P | SU-9516
PDB Ligand
Compound class: Synthetic organic
Comment: SU9516 is a potent inhibitor of several cyclin-dependent kinases (CDKs) with reported selectivity for CDK2 [4]. Later analysis of SU9516's selectivity profile indicates a similar level of potency as an inhibitor of CDK5/p25 compared to CDK2 [3]. Inhibition of CDK5 was confirmed in a cellular assay measuring dephosphorylation of pFAK(S732). SU9516 also arrests cells at the G2/M phase in cells lacking CDK2, in which case it must be causing the cell cycle arrest via inhibition of CDK1 [3].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 67.01
Molecular weight 241.09
XLogP 0.97
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES COc1ccc2c(c1)C(=Cc1cnc[nH]1)C(=O)N2
Isomeric SMILES COc1ccc2c(c1)/C(=C/c1cnc[nH]1)/C(=O)N2
InChI InChI=1S/C13H11N3O2/c1-18-9-2-3-12-10(5-9)11(13(17)16-12)4-8-6-14-7-15-8/h2-7H,1H3,(H,14,15)(H,16,17)/b11-4-
InChI Key QNUKRWAIZMBVCU-WCIBSUBMSA-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. 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]
3. Jorda R, Hendrychová D, Voller J, Řezníčková E, Gucký T, Kryštof V. (2018)
How Selective Are Pharmacological Inhibitors of Cell-Cycle-Regulating Cyclin-Dependent Kinases?.
J. Med. Chem., 61 (20): 9105-9120. [PMID:30234987]
4. Lane ME, Yu B, Rice A, Lipson KE, Liang C, Sun L, Tang C, McMahon G, Pestell RG, Wadler S. (2001)
A novel cdk2-selective inhibitor, SU9516, induces apoptosis in colon carcinoma cells.
Cancer Res., 61 (16): 6170-7. [PMID:11507069]