GSK864   Click here for help

GtoPdb Ligand ID: 8961

Synonyms: compound 4 [PMID: 26436839]
Compound class: Synthetic organic
Comment: GSK864 is a potent and selective allosteric inhibitor of mutant isocitrate dehydrogenase 1 (IDH1) [1]. The compound is available from the Structural Genomics Consortium, from their Epigenetics Probes Collection.
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 CDK toolkit. 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 7
Hydrogen bond donors 3
Rotatable bonds 9
Topological polar surface area 135.34
Molecular weight 558.24
XLogP 3.02
No. Lipinski's rules broken 0
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.

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Canonical SMILES COc1c(C)cc(cc1C)NC(=O)c1nn(c2c1CN(CC2(C)C(=O)N)C(=O)c1[nH]ccc1)Cc1ccc(cc1)F
Isomeric SMILES COc1c(C)cc(cc1C)NC(=O)c1nn(c2c1CN(C[C@]2(C)C(=O)N)C(=O)c1[nH]ccc1)Cc1ccc(cc1)F
InChI InChI=1S/C30H31FN6O4/c1-17-12-21(13-18(2)25(17)41-4)34-27(38)24-22-15-36(28(39)23-6-5-11-33-23)16-30(3,29(32)40)26(22)37(35-24)14-19-7-9-20(31)10-8-19/h5-13,33H,14-16H2,1-4H3,(H2,32,40)(H,34,38)/t30-/m0/s1
InChI Key DUCNNEYLFOQFSW-PMERELPUSA-N
References
1. Okoye-Okafor UC, Bartholdy B, Cartier J, Gao EN, Pietrak B, Rendina AR, Rominger C, Quinn C, Smallwood A, Wiggall KJ et al.. (2015)
New IDH1 mutant inhibitors for treatment of acute myeloid leukemia.
Nat Chem Biol, 11 (11): 878-86. [PMID:26436839]
2. SGC. 
GSK864 Inhibitor for mutant isocitrate dehydrogenase.
Accessed on 16/12/2015. Modified on 04/08/2023. thesgc.org, https://www.thesgc.org/chemical-probes/GSK864