VPC 44116 | 857346

(R)-(3-amino-4-((3-octylphenyl)amino)-4-oxobutyl)phosphonic acid




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In addition to receptor-selective agonists such as SEW2871, competitive S1P receptor antagonists have provided insight into the physiological effects of S1P signaling, particularly involving S1P1. (R)-3-amino-(3-octylphenylamino)-4-oxobutylphosphonic acid (VPC44116) (S1P1/3 antagonist) and an analog, (R)-3-amino-(3-hexylphenylamino)-4-oxobutylphosphonic acid (W146) (S1P1 antagonist), both were found to increase capillary permeability as measured by Evans blue dye leakage in mouse lung tissue. Kennedy, P.C., et al. (2011). Also refer Sanna et al., 2006 and Foss et al., 2007.This product is covered by Patent Number US 7,888,527 B2. Avanti manufactures this under license from University of Virginia
Molecular Formula
Percent Composition
C 58.36%, H 8.44%, N 7.56%, O 17.28%, P 8.36%
1 year
CAS Number
CAS Registry Number is a Registered Trademark of the American Chemical Society
Molecular Weight
Exact Mass
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GIF Graphics File. 
MDL Molfile. 
CDX File. 
Kennedy, P.C., R. Zhu, T. Huang, J.L. Tomsig, T.P. Mathews, M. David, O. Peyruchaud, T.L. Macdonald, and K.R. Lynch. (2011). Characterization of a sphingosine 1-phosphate receptor antagonist prodrug.  J Pharmacol Exp Ther 338:879-89. [PubMed]Sanna, M.G., S.K. Wang, P.J. Gonzalez-Cabrera, A. Don, D. Marsolais, M.P. Matheu, S.H. Wei, I. Parker, E. Jo, W.C. Cheng, M.D. Cahalan, C.H. Wong, and H. Rosen. (2006). Enhancement of capillary leakage and restoration of lymphocyte egress by a chiral S1P1 antagonist in vivo.  Nat Chem Biol 2:434-41. [PubMed]Foss, F.W. Jr, A.H. Snyder, M.D. Davis, M. Rouse, M.D. Okusa, K.R. Lynch, and T.L. Macdonald. (2007). Synthesis and biological evaluation of gamma-aminophosphonates as potent, subtype-selective sphingosine 1-phosphate receptor agonists and antagonists.  Bioorg Med Chem 15:663-77. [PubMed]