compound 5b [PMID: 29457898]   Click here for help

GtoPdb Ligand ID: 9835

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Vβ9/Vδ2 T-cells have been shown to be activated by small molecule phosphoantigens (PAgs). The aryloxy triester phosphoramidate prodrug ProPAgen 5b is a potent and specific activator of these cells as a potential immunotherapeutic agent [1]. The molecular mechanism of action is unkown but evidence supports PAgs binding the intracellular B30.2 domain of butyrophilin 3A1.
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 15
Topological polar surface area 92.9
Molecular weight 533.24
XLogP 5.9
No. Lipinski's rules broken 2
Click here for help
Canonical SMILES CC(=CCOP(=O)(NC(C(=O)OCc1ccccc1)C)Oc1ccccc1)CO[Si](C(C)(C)C)(C)C
Isomeric SMILES C/C(=C\COP(=O)(N[C@H](C(=O)OCc1ccccc1)C)Oc1ccccc1)/CO[Si](C(C)(C)C)(C)C
InChI InChI=1S/C27H40NO6PSi/c1-22(20-33-36(6,7)27(3,4)5)18-19-32-35(30,34-25-16-12-9-13-17-25)28-23(2)26(29)31-21-24-14-10-8-11-15-24/h8-18,23H,19-21H2,1-7H3,(H,28,30)/b22-18+/t23-,35?/m0/s1
1. Davey MS, Malde R, Mykura RC, Baker AT, Taher TE, Le Duff CS, Willcox BE, Mehellou Y. (2018)
Synthesis and Biological Evaluation of ( E)-4-Hydroxy-3-methylbut-2-enyl Phosphate (HMBP) Aryloxy Triester Phosphoramidate Prodrugs as Activators of Vγ9/Vδ2 T-Cell Immune Responses.
J Med Chem, 61 (5): 2111-2117. [PMID:29457898]