AZ2   Click here for help

GtoPdb Ligand ID: 10233

PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: AZ2 is a highly selective inhibitor of the lipid kinase PI3Kγ [1]. It represents a novel chemotype that binds to a conserved part of the ATP-binding pocket (Type I inhibitor-like), but once bound the inhibitor induces a DFG-out (active state) conformational change and rearrangement of the activation loop (analogous to Type II protein kinase inhibitors). This mechanism occurs only in PI3Kγ. Analogues of this novel class of PI3Kγ inhibitors, with enhanced pharmacokinetic properties and in vivo potency (e.g. Compound 15 [PMID: 29852070]), have been reported [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 90.54
Molecular weight 369.15
XLogP 2.83
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CC(=O)Nc1sc(c(n1)C)c1cc(C)c2c(c1)CN(C2=O)C(C1CC1)C
Isomeric SMILES CC(=O)Nc1sc(c(n1)C)c1cc(C)c2c(c1)CN(C2=O)[C@H](C1CC1)C
InChI InChI=1S/C20H23N3O2S/c1-10-7-15(18-11(2)21-20(26-18)22-13(4)24)8-16-9-23(19(25)17(10)16)12(3)14-5-6-14/h7-8,12,14H,5-6,9H2,1-4H3,(H,21,22,24)/t12-/m0/s1
InChI Key CNCRCDLWUGCPSJ-LBPRGKRZSA-N
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Molecular structure representations generated using Open Babel