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.
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2D Structure
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Physico-chemical Properties
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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
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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
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]