rigosertib   Click here for help

GtoPdb Ligand ID: 7833

Synonyms: Estybon® (proposed trade name) | ON-01910 | ON01910.Na
PDB Ligand
Compound class: Synthetic organic
Comment: Rigosertib is a dual kinase inhibitor, affecting the phosphoinositide 3-kinase (PI3K) and polo-like kinase 1 (PLK1) pathways. Note that the inhibitory action on PLK1 has been disputed [2]. It is a non-ATP-competitive inhibitor, meaning it inhibits substrate binding to the enzyme.
Note that some bioactivity data may be associated with the sodium salt, PubChem CID 23696523.
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 2
Rotatable bonds 11
Topological polar surface area 128.77
Molecular weight 451.13
XLogP 2.28
No. Lipinski's rules broken 1

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 COc1cc(OC)cc(c1C=CS(=O)(=O)Cc1ccc(c(c1)NCC(=O)O)OC)OC
Isomeric SMILES COc1cc(OC)cc(c1/C=C/S(=O)(=O)Cc1ccc(c(c1)NCC(=O)O)OC)OC
InChI InChI=1S/C21H25NO8S/c1-27-15-10-19(29-3)16(20(11-15)30-4)7-8-31(25,26)13-14-5-6-18(28-2)17(9-14)22-12-21(23)24/h5-11,22H,12-13H2,1-4H3,(H,23,24)/b8-7+
InChI Key OWBFCJROIKNMGD-BQYQJAHWSA-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. Lu T, Laughton CA, Wang S, Bradshaw TD. (2015)
In vitro antitumor mechanism of (E)-N-(2-methoxy-5-(((2,4,6-trimethoxystyryl)sulfonyl)methyl)pyridin-3-yl)methanesulfonamide.
Mol Pharmacol, 87 (1): 18-30. [PMID:25316768]
2. Steegmaier M, Hoffmann M, Baum A, Lénárt P, Petronczki M, Krssák M, Gürtler U, Garin-Chesa P, Lieb S, Quant J et al.. (2007)
BI 2536, a potent and selective inhibitor of polo-like kinase 1, inhibits tumor growth in vivo.
Curr Biol, 17 (4): 316-22. [PMID:17291758]