compound 15 [PMID: 32045236]   Click here for help

GtoPdb Ligand ID: 10706

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Compound 15 is a small molecule, ADP analogue-based CD73 (ecto-5'-nucleotidase) inhibitor [1]. Mechanisms to inhibit CD73 activity are being exploited for immuno-oncology potential, and are exemplified by the progress of the anti-CD73 monoclonal oleclumab and the small molecule inhibitor quemliclustat into clinical trials as treatments for advanced solid tumours.
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 13
Hydrogen bond donors 6
Rotatable bonds 6
Topological polar surface area 242.99
Molecular weight 550.95
XLogP -2.87
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES O[C@@H]1[C@@H](COP(=O)(CP(=O)(O)O)O)O[C@H]([C@@H]1O)n1cnc2c1nc(I)nc2N
Isomeric SMILES O[C@@H]1[C@@H](COP(=O)(CP(=O)(O)O)O)O[C@H]([C@@H]1O)n1cnc2c1nc(I)nc2N
InChI InChI=1S/C11H16IN5O9P2/c12-11-15-8(13)5-9(16-11)17(2-14-5)10-7(19)6(18)4(26-10)1-25-28(23,24)3-27(20,21)22/h2,4,6-7,10,18-19H,1,3H2,(H,23,24)(H2,13,15,16)(H2,20,21,22)/t4-,6-,7-,10-/m1/s1
InChI Key OJRUSAPKCPIVBY-KQYNXXCUSA-N
References
1. Bhattarai S, Pippel J, Scaletti E, Idris R, Freundlieb M, Rolshoven G, Renn C, Lee SY, Abdelrahman A, Zimmermann H et al.. (2020)
2-Substituted α,β-Methylene-ADP Derivatives: Potent Competitive Ecto-5'-nucleotidase (CD73) Inhibitors with Variable Binding Modes.
J Med Chem, 63 (6): 2941-2957. [PMID:32045236]