JAK inhibitor 20a   Click here for help

GtoPdb Ligand ID: 10147

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Inhibitor 20a represents a novel chemotype for Janus kinase inhibitors; benzo[ c]pyrrolo[2,3- h][1,6]naphthyridin-5-one (BPN) [1]. It was identified using sequential palladium catalysis.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 113.24
Molecular weight 445.18
XLogP 2.34
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES N#CC1CN(C1)C(=O)C(n1c(=O)c2cc(OC)c(cc2c2c1c1cc[nH]c1nc2)OC)CC
Isomeric SMILES N#CC1CN(C1)C(=O)[C@H](n1c(=O)c2cc(OC)c(cc2c2c1c1cc[nH]c1nc2)OC)CC
InChI InChI=1S/C24H23N5O4/c1-4-18(24(31)28-11-13(9-25)12-28)29-21-14-5-6-26-22(14)27-10-17(21)15-7-19(32-2)20(33-3)8-16(15)23(29)30/h5-8,10,13,18H,4,11-12H2,1-3H3,(H,26,27)/t18-/m1/s1
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Janus kinase 1 Hs Inhibitor Inhibition 8.5 pIC50 - 1
pIC50 8.5 (IC50 3.37x10-9 M) [1]
Janus kinase 2 Hs Inhibitor Inhibition 7.5 pIC50 - 1
pIC50 7.5 (IC50 2.96x10-8 M) [1]
tyrosine kinase 2 Hs Inhibitor Inhibition 7.1 pIC50 - 1
pIC50 7.1 (IC50 7.37x10-8 M) [1]
Janus kinase 3 Hs Inhibitor Inhibition 6.9 pIC50 - 1
pIC50 6.9 (IC50 1.144x10-7 M) [1]