SGX-523   Click here for help

GtoPdb Ligand ID: 5709

Synonyms: SGX523
PDB Ligand
Compound class: Synthetic organic
Comment: SGX-523 is an ATP-competitive, highly selective inhibitor of the receptor tyrosine kinase, hepatocyte growth factor receptor (MET) [1] [2]. While Buchanan et al. [1] include three PDB structures linked via PubMed to MMDB entries, two of them depict a charge-state tautomer of SGX-523. These thus point to a different compound PubChem CID 42628064 but the PDB link above points to the correct ligand structure. Note also, becasue of its established specificity, this now has a SGC Probe Portal entry SGX-523.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 99.09
Molecular weight 359.1
XLogP 4.78
No. Lipinski's rules broken 0
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Canonical SMILES Cn1ncc(c1)c1ccc2n(n1)c(nn2)Sc1ccc2c(c1)cccn2
Isomeric SMILES Cn1ncc(c1)c1ccc2n(n1)c(nn2)Sc1ccc2c(c1)cccn2
InChI InChI=1S/C18H13N7S/c1-24-11-13(10-20-24)16-6-7-17-21-22-18(25(17)23-16)26-14-4-5-15-12(9-14)3-2-8-19-15/h2-11H,1H3
1. Buchanan SG, Hendle J, Lee PS, Smith CR, Bounaud PY, Jessen KA, Tang CM, Huser NH, Felce JD, Froning KJ et al.. (2009)
SGX523 is an exquisitely selective, ATP-competitive inhibitor of the MET receptor tyrosine kinase with antitumor activity in vivo.
Mol Cancer Ther, 8 (12): 3181-90. [PMID:19934279]
2. Chemicalprobes team. 
Accessed on 11/07/2016. Modified on 11/07/2016.,
3. 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]
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]