dezapelisib   Click here for help

GtoPdb Ligand ID: 9728

Synonyms: compound 67 [PMID: 22924688] | example 15 [WO2011008487] [2] | INCB 40093 | INCB40093
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Dezapelisib (INCB 40093) is a potent and selective PIK3δ inhibitor that was being developed as a potential therapy for B cell malignancies [1]. Claimed as example 15 in patent WO2011008487, although only binned IC50 values are contained in this patent document [2].
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 129.1
Molecular weight 421.11
XLogP 3.56
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
Click here for help

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/)

✖
Canonical SMILES Fc1cccc(c1)c1c(nc2n(c1=O)c(C)cs2)C(Nc1ncnc2c1nc[nH]2)C
Isomeric SMILES Fc1cccc(c1)c1c(nc2n(c1=O)c(C)cs2)[C@@H](Nc1ncnc2c1nc[nH]2)C
InChI InChI=1S/C20H16FN7OS/c1-10-7-30-20-27-15(11(2)26-18-16-17(23-8-22-16)24-9-25-18)14(19(29)28(10)20)12-4-3-5-13(21)6-12/h3-9,11H,1-2H3,(H2,22,23,24,25,26)/t11-/m0/s1
InChI Key RSIWALKZYXPAGW-NSHDSACASA-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/)
Bioactivity Comments
Dezapelisib inhibits proliferation of isolated human B cells and Pfeiffer diffuse large B cell lymphoma cells with IC50 values of <50 nM [2].
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit delta Primary target of this compound Hs Inhibitor Inhibition >7.3 pIC50 - 2
⤷ pIC50 >7.3 (IC50 <5x10-8 M) [2]
Description: The same value was obtained using an enzyme activity assay and a scintillation proximity assay.
phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit alpha Hs Inhibitor Inhibition <6.3 pIC50 - 2
⤷ pIC50 <6.3 (IC50 >5x10-7 M) [2]
phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit beta Hs Inhibitor Inhibition <6.3 pIC50 - 2
⤷ pIC50 <6.3 (IC50 >5x10-7 M) [2]
phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit gamma Hs Inhibitor Inhibition <6.3 pIC50 - 2
⤷ pIC50 <6.3 (IC50 >5x10-7 M) [2]