SU11652   

GtoPdb Ligand ID: 6043

Synonyms: SU-11652
Compound class: Synthetic organic
Comment: SU11652 is a cell-permeable compound that acts as a potent, reversible, and ATP-competitive tyrosine kinase receptor inhibitor. The synthesis and discovery of this compound is decribed in [4], where it is compound 12c.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 77.23
Molecular weight 414.18
XLogP 3.4
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CCN(CCNC(=O)c1c(C)[nH]c(c1C)C=C1C(=O)Nc2c1cc(Cl)cc2)CC
Isomeric SMILES CCN(CCNC(=O)c1c(C)[nH]c(c1C)/C=C/1\C(=O)Nc2c1cc(Cl)cc2)CC
InChI InChI=1S/C22H27ClN4O2/c1-5-27(6-2)10-9-24-22(29)20-13(3)19(25-14(20)4)12-17-16-11-15(23)7-8-18(16)26-21(17)28/h7-8,11-12,25H,5-6,9-10H2,1-4H3,(H,24,29)(H,26,28)/b17-12-
InChI Key XPLJEFSRINKZLC-ATVHPVEESA-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. Fedorov O, Marsden B, Pogacic V, Rellos P, Müller S, Bullock AN, Schwaller J, Sundström M, Knapp S. (2007)
A systematic interaction map of validated kinase inhibitors with Ser/Thr kinases.
Proc. Natl. Acad. Sci. U.S.A., 104 (51): 20523-8. [PMID:18077363]
3. 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]
4. Sun L, Liang C, Shirazian S, Zhou Y, Miller T, Cui J, Fukuda JY, Chu JY, Nematalla A, Wang X et al.. (2003)
Discovery of 5-[5-fluoro-2-oxo-1,2- dihydroindol-(3Z)-ylidenemethyl]-2,4- dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylaminoethyl)amide, a novel tyrosine kinase inhibitor targeting vascular endothelial and platelet-derived growth factor receptor tyrosine kinase.
J. Med. Chem., 46 (7): 1116-9. [PMID:12646019]