voxtalisib   Click here for help

GtoPdb Ligand ID: 7964

Synonyms: SAR-245409 | SAR245409 | XL765
Compound class: Synthetic organic
Comment: Voxtalisib is an orally bioavailable small molecule inhibitor of phosphatidylinositol 3 kinase (PI3K) and mammalian target of rapamycin (mTOR) kinases in the PI3K/mTOR signaling pathway, with potential antineoplastic activity [1].
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 8
Hydrogen bond donors 3
Rotatable bonds 11
Topological polar surface area 149.15
Molecular weight 599.18
XLogP 5.26
No. Lipinski's rules broken 1
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 COc1cc(OC)cc(c1)Nc1nc2ccccc2nc1NS(=O)(=O)c1ccc(cc1)NC(=O)c1ccc(c(c1)OC)C
Isomeric SMILES COc1cc(OC)cc(c1)Nc1nc2ccccc2nc1NS(=O)(=O)c1ccc(cc1)NC(=O)c1ccc(c(c1)OC)C
InChI InChI=1S/C31H29N5O6S/c1-19-9-10-20(15-28(19)42-4)31(37)33-21-11-13-25(14-12-21)43(38,39)36-30-29(34-26-7-5-6-8-27(26)35-30)32-22-16-23(40-2)18-24(17-22)41-3/h5-18H,1-4H3,(H,32,34)(H,33,37)(H,35,36)
InChI Key HJSSPYJVWLTYHG-UHFFFAOYSA-N
Bioactivity Comments
There is no publicly available peer-reveiwed bioactivity data for this compound to support its molecular mechanism of action. Some data is provided online and appears to be taken from meeting abstracts, although the abstracts themselves do not contain the quoted information. For example Garcia-Echeverria and Sellers (2008) [1] quote IC50s for XL765 at PI3Kα, (39nM), β (113nM), γ (9nM) and δ (43nM) and DNA-PK (150nM) and mTOR (157nM) and reference this to two AACR meeting abstracts; Patnaik et al. (2007) Biomarker development for XL765, a potent and selective oral dual inhibitor of PI3K and mTOR currently being administered to patients in a Phase I clinical trial (Abstract B265) and Laird (2007) XL765 targets tumor growth, survival, and angiogenesis in preclinical models by dual inhibition of PI3K and mTOR, (Abstract B250), but neither of these abstracts contain this quoted data.