| Stereochemistry | ACHIRAL |
| Molecular Formula | C18H15OP |
| Molecular Weight | 278.2849 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O=P(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3
InChI
InChIKey=FIQMHBFVRAXMOP-UHFFFAOYSA-N
InChI=1S/C18H15OP/c19-20(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H
Triphenylphosphine oxide (TPPO) is a neurotoxic very stable polar compound present in waste organic solutions from the chemical and pharmaceutical industry. The acute toxicity of TPPO LC50=12.2µg/mL, LC90=29.5µg/mL is higher than triphenyltin acetate so that a correct management in the relationship with sustainable chemistry is strongly required. TPPO was identified as a selective and potent inhibitor of transient receptor potential melastatin-5 (TRPM5), but at the same moment, it had no effect (up to 100 μM) on the membrane potential responses of TRPA1, TRPV1, or TRPM4b.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 12.0 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
Sample Use Guides
Using recombinant transient receptor potential melastatin-5 (TRPM5) -expressing cells in a fluorescence imaging plate reader-based membrane potential assay, was identified triphenylphosphine oxide (TPPO) as a selective and potent inhibitor of TRPM5. TPPO inhibited both human (IC₅₀ = 12 μM) and murine TRPM5 (IC₅₀ = 30 μM) heterologously expressed in HEK293 cells, but had no effect (up to 100 μM) on the membrane potential responses of TRPA1, TRPV1, or TRPM4b. TPPO also inhibited a calcium-gated TRPM5-dependent conductance in taste cells isolated from the tongues of transgenic TRPM5(+/)⁻ mice.
SUBSTANCE RECORD
