copanlisib   Click here for help

GtoPdb Ligand ID: 7875

Synonyms: Aliqopa® | BAY 80-6946 | BAY80-6946
Approved drug PDB Ligand
copanlisib is an approved drug (FDA (2017))
Compound class: Synthetic organic
Comment: Copanlisib is a phosphoinositide 3-kinase (PI3K) inhibitor [2], preferentially inhibiting PI3Kα and PI3Kβ, and with significant antineoplastic activity [3]. The compound has less potent mTOR activity.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 142.01
Molecular weight 480.22
XLogP 1.76
No. Lipinski's rules broken 0
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Canonical SMILES COc1c(OCCCN2CCOCC2)ccc2c1nc(=NC(=O)c1cnc(nc1)N)n1c2NCC1
Isomeric SMILES COc1c(OCCCN2CCOCC2)ccc2c1nc(=NC(=O)c1cnc(nc1)N)n1c2NCC1
InChI InChI=1S/C23H28N8O4/c1-33-19-17(35-10-2-6-30-8-11-34-12-9-30)4-3-16-18(19)28-23(31-7-5-25-20(16)31)29-21(32)15-13-26-22(24)27-14-15/h3-4,13-14,25H,2,5-12H2,1H3,(H2,24,26,27)
Bioactivity Comments
Copanlisib inhibits PI3Kα-dependent phosphorylation of Akt with an IC50 of 0.4-0.6 nM in KPL4 cells [2]. In LPA stimulated PC3 cells, the IC50 for PI3Kβ-dependent Akt phosphorylation was 7.8-10 nM [2].
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 alpha Hs Inhibitor Inhibition 9.3 pIC50 - 2
pIC50 9.3 (IC50 5x10-10 M) [2]
phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit delta Hs Inhibitor Inhibition 9.1 pIC50 - 2
pIC50 9.1 (IC50 7x10-10 M) [2]
phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit beta Hs Inhibitor Inhibition 8.4 pIC50 - 2
pIC50 8.4 (IC50 3.7x10-9 M) [2]
phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit gamma Hs Inhibitor Inhibition 8.2 pIC50 - 2
pIC50 8.2 (IC50 6.4x10-9 M) [2]
mechanistic target of rapamycin kinase Hs Inhibitor Inhibition 7.3 pIC50 - 2
pIC50 7.3 (IC50 4.5x10-8 M) [2]