GSK2256098   Click here for help

GtoPdb Ligand ID: 7939

Synonyms: GSK-2256098
Compound class: Synthetic organic
Comment: GSK2256098 is a small molecule focal adhesion kinase (FAK) inhibitor with potential antiangiogenic and antineoplastic activity [1,3-4].
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 93.1
Molecular weight 414.16
XLogP 4.67
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CONC(=O)c1ccccc1Nc1cc(ncc1Cl)Nc1cc(nn1C(C)C)C
Isomeric SMILES CONC(=O)c1ccccc1Nc1cc(ncc1Cl)Nc1cc(nn1C(C)C)C
InChI InChI=1S/C20H23ClN6O2/c1-12(2)27-19(9-13(3)25-27)24-18-10-17(15(21)11-22-18)23-16-8-6-5-7-14(16)20(28)26-29-4/h5-12H,1-4H3,(H,26,28)(H2,22,23,24)
InChI Key BVAHPPKGOOJSPU-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Auger KR , Smitheman KN , Korenchuk S, McHugh C, Kruger R , Van Aller GS , Smallwood A, Gontarek RR, Faitg T , Johnson N. (2012)
387 The Focal Adhesion Kinase Inhibitor GSK2256098: a Potent and Selective Inhibitor for the Treatment of Cancer [Abstract].
European Journal of Cancer, 28 (Supplement 6).
2. GSK. 
Mesothelioma drug slows disease progression in patients with an inactive NF2 gene.
Accessed on 18/11/2014. Modified on 18/11/2014. sciencedaily.com, http://www.sciencedaily.com/releases/2012/11/121108181445.htm
3. Lee BY, Timpson P, Horvath LG, Daly RJ. (2015)
FAK signaling in human cancer as a target for therapeutics.
Pharmacol Ther, 146: 132-49. [PMID:25316657]
4. Schultze A, Fiedler W. (2011)
Clinical importance and potential use of small molecule inhibitors of focal adhesion kinase.
Anticancer Agents Med Chem, 11 (7): 593-9. [PMID:21787277]
5. Zhang J, He DH, Zajac-Kaye M, Hochwald SN. (2014)
A small molecule FAK kinase inhibitor, GSK2256098, inhibits growth and survival of pancreatic ductal adenocarcinoma cells.
Cell Cycle, 13 (19): 3143-9. [PMID:25486573]