SU-14813   

GtoPdb Ligand ID: 5712

Synonyms: SU014813 | SU14813
Compound class: Synthetic organic
Comment: SU-14813 is an oral, multitargeted receptor tyrosine kinase inhibitor targeting VEGFRs, PDGFRs, KIT, and FLT3 [2-3].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 8
Hydrogen bond donors 3
Rotatable bonds 7
Topological polar surface area 103.26
Molecular weight 442.2
XLogP -0.66
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES OC(CN1CCOCC1)CNC(=O)C1C(=NC(=C1C)C=C1C(=O)Nc2c1cc(F)cc2)C
Isomeric SMILES O[C@H](CN1CCOCC1)CNC(=O)C1C(=NC(=C1C)/C=C/1\C(=O)Nc2c1cc(F)cc2)C
InChI InChI=1S/C23H27FN4O4/c1-13-20(10-18-17-9-15(24)3-4-19(17)27-22(18)30)26-14(2)21(13)23(31)25-11-16(29)12-28-5-7-32-8-6-28/h3-4,9-10,16,21,29H,5-8,11-12H2,1-2H3,(H,25,31)(H,27,30)/b18-10-/t16-,21?/m0/s1
InChI Key XWPFYHDOZULRTD-ROUJOJKSSA-N
References
1. 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]
2. Hu-Lowe D, Brega N, Patyna S. (2011)
The discovery and development of SU14813, a next-generation multitargeted tyrosine kinase inhibitor for the treatment of human malignancies.
Mol. Cancer Ther., 10 (11): 2015. [PMID:22072801]
3. Patyna S, Laird AD, Mendel DB, O'farrell AM, Liang C, Guan H, Vojkovsky T, Vasile S, Wang X, Chen J et al.. (2006)
SU14813: a novel multiple receptor tyrosine kinase inhibitor with potent antiangiogenic and antitumor activity.
Mol. Cancer Ther., 5 (7): 1774-82. [PMID:16891463]
4. 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]