compound 52 [PMID: 28541707]   Click here for help

GtoPdb Ligand ID: 10001

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Compound 52 is reported as a potent and selective PI3Kδ inhibitor [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 120.62
Molecular weight 471.16
XLogP 2.27
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES N#Cc1ccc(cc1N1CCN(C(C1=O)(C)C)C(=O)C)c1cc(c2n1ncnc2N)C(F)(F)F
Isomeric SMILES N#Cc1ccc(cc1N1CCN(C(C1=O)(C)C)C(=O)C)c1cc(c2n1ncnc2N)C(F)(F)F
InChI InChI=1S/C22H20F3N7O2/c1-12(33)31-7-6-30(20(34)21(31,2)3)16-8-13(4-5-14(16)10-26)17-9-15(22(23,24)25)18-19(27)28-11-29-32(17)18/h4-5,8-9,11H,6-7H2,1-3H3,(H2,27,28,29)
InChI Key ZDXIDBRGTYDHBQ-UHFFFAOYSA-N
Bioactivity Comments
Compound 52 is active in cellular assays measuring inhibition of T cell activation and IFNγ production [2] In a kinase profile screen, off-targets with IC50s in the nanomolar range (IC50 in parentheses) are PI3Kγ (41 nM), MINK1 (66 nM), PI3Kα (370 nM), MLCK (510 nM) and CLK4 (700 nM).
Selectivity at enzymes
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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 8.8 pIC50 - 2
pIC50 8.8 (IC50 1.7x10-9 M) [2]
phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit gamma Hs Inhibitor Inhibition 6.8 pIC50 - 2
pIC50 6.8 (IC50 1.7x10-7 M) [2]
Description: Calculated based on potency being 100-fold lower for PI3Kγ than for PI3Kδ.
phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit alpha Hs Inhibitor Inhibition 5.9 pIC50 - 2
pIC50 5.9 (IC50 1.19x10-6 M) [2]
Description: Calculated based on 700-fold lower than affinity for PI3Kδ.