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
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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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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
InChI Key OAOYKSGPQULCDH-WHZCJLAPSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
Benzyl ((((E)-4-((tert-Butyldimethylsilyl)oxy)-3-methylbut-2-en-1-yl)oxy)(phenoxy)phosphoryl)-L-alaninate
Database Links Click here for help
GtoPdb PubChem SID 363894129
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