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(2S)-OMPT
Cayman Chemical Item Number 10005707
Description
Lysophosphatidic acid (LPA) is a potent lipid mediator that elicits its effect through four distinct receptors - LPA1/EDG-2, LPA2/EDG-4, LPA3/EDG-7 and LPA4/GPR23.1↗,2↗ OMPT is a selective agonist of the LPA3 receptor. It exhibits EC50 values of 68 nM and >6.8 µM for calcium mobilization in LPA3 and LPA2-expressing Sf9 cells, respectively.3↗ The (2S)-OMPT enantiomer is 5- to 20-fold more active than (2R)-OMPT in calcium release assays in both LPA3-transfected Sf9 and rat hepatoma Rh7777 cells.4↗
1 Chun, J., Goetzl, E.J., Hla, T., et al. International union of pharmacology. XXXIV. Lysophospholipid receptor nomenclature. Pharmacol Rev 54 265-269 (2002).
2 Niu, S., Mitchell, D.C., and Litman, B.J. Trans fatty acid derived phospholipids show increased membrane cholesterol and reduced receptor activation as compared to their cis analogs. Biochemistry 44 4458-4465 (2005).
3 Hasegawa, Y., Erickson, J.R., Goddard, G.J., et al. Identification of a phosphothionate analogue of lysophosphatidic acid (LPA) as a selective agonist of the LPA3 receptor. J Biol Chem 278(14) 11962-11969 (2003).
4 Qian, L., Xu, Y., Hasegawa, Y., et al. Enantioselective responses to a phosphorothioate analogue of lysophosphatidic acid with LPA3 receptor-selective agonist activity. J Med Chem 46 5575-5578 (2003).
Formal Name (2S)-3-[(hydroxymercaptophosphinyl)oxy]-2-methoxypropyl ester, 9Z-octadecenoic acid, triethyl ammonium salt
CAS Number 1217471-69-6
Molecular Formula C22H43O6PS • 2(C2H5)3N
Formula Weight 669.0
Formulation A solution in ethanol:chloroform (1:1)
Purity ≥98%
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES O=C(OC[C@H](OC)COP(O)(O)=S)CCCCCCC/C=C\CCCCCCCC
InCHI Code 1S/C22H43O6PS/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-22(23)27-19-21(26-2)20-28-29(24,25)30/h10-11,21H,3-9,12-20H2,1-2H3,(H2,24,25,30)/b11-10-/t21-/m0/s1
InCHI Key FCVJYKICQNLXAX-XPTLAUCJSA-N |