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Chemical Compound Review

AC1NR9T0     [(2R)-1-(hydroxy-oxido- phosphoryl)oxy-3...

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Disease relevance of [(2R)-2-pentadecanoyloxy-3-tridecanoyloxy-propoxy]phosphonic acid


Psychiatry related information on [(2R)-2-pentadecanoyloxy-3-tridecanoyloxy-propoxy]phosphonic acid


High impact information on [(2R)-2-pentadecanoyloxy-3-tridecanoyloxy-propoxy]phosphonic acid


Chemical compound and disease context of [(2R)-2-pentadecanoyloxy-3-tridecanoyloxy-propoxy]phosphonic acid


Biological context of [(2R)-2-pentadecanoyloxy-3-tridecanoyloxy-propoxy]phosphonic acid


Anatomical context of [(2R)-2-pentadecanoyloxy-3-tridecanoyloxy-propoxy]phosphonic acid

  • Our evidence suggests that in neutrophils, PI breakdown and PA labelling are both consequences and not causes of a rise in intracellular Ca2+ [22].
  • Both biochemical and genetic data indicate that regulation of the membrane content of phosphatidic acid, diacylglycerol and phosphoinositides is necessary for protein traffic from the Golgi complex [23].
  • On the other hand, phosphatidic acid, the physiologic product of phospholipase D action on phospholipids, was found to mimic the effect of anti-Kp43 monoclonal antibody regarding tumor necrosis factor alpha (TNF-alpha) biosynthesis and secretion by NK cells [24].
  • This study examines two calcium-dependent membrane processes that have been observed in erythrocytes from healthy individuals: calcium-stimulated phosphatidic acid accumulation and calcium-induced potassium leak [25].
  • Phospholipase D-modified low density lipoprotein is taken up by macrophages at increased rate. A possible role for phosphatidic acid [26].

Associations of [(2R)-2-pentadecanoyloxy-3-tridecanoyloxy-propoxy]phosphonic acid with other chemical compounds


Gene context of [(2R)-2-pentadecanoyloxy-3-tridecanoyloxy-propoxy]phosphonic acid


Analytical, diagnostic and therapeutic context of [(2R)-2-pentadecanoyloxy-3-tridecanoyloxy-propoxy]phosphonic acid


  1. Phosphatidic acid signaling mediates lung cytokine expression and lung inflammatory injury after hemorrhage in mice. Abraham, E., Bursten, S., Shenkar, R., Allbee, J., Tuder, R., Woodson, P., Guidot, D.M., Rice, G., Singer, J.W., Repine, J.E. J. Exp. Med. (1995) [Pubmed]
  2. Protection from endotoxic shock in mice by pharmacologic inhibition of phosphatidic acid. Rice, G.C., Brown, P.A., Nelson, R.J., Bianco, J.A., Singer, J.W., Bursten, S. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  3. Myotonic dystrophy: calcium-dependent phosphatidic acid synthesis in erythrocytes. Moore, R.B., Appel, S.H., Plishker, G.A. Ann. Neurol. (1981) [Pubmed]
  4. Phospholipid metabolism of hypothermically stored rat hepatocytes. Kim, J.S., Southard, J.H. Hepatology (1999) [Pubmed]
  5. Activation of phospholipase D in human platelets by collagen and thrombin and its relationship to platelet aggregation. Chiang, T.M. Biochim. Biophys. Acta (1994) [Pubmed]
  6. Abnormal phosphatidylinositol-cycle of platelet membrane in schizophrenia--a preliminary study. Kaiya, H., Takeuchi, K., Namba, M., Imai, A., Nakashima, S., Nozawa, Y. Folia psychiatrica et neurologica japonica. (1984) [Pubmed]
  7. Regulation of eukaryotic phosphatidylinositol-specific phospholipase C and phospholipase D. Singer, W.D., Brown, H.A., Sternweis, P.C. Annu. Rev. Biochem. (1997) [Pubmed]
  8. Phosphatidylinositol 4-phosphate 5-kinase alpha is a downstream effector of the small G protein ARF6 in membrane ruffle formation. Honda, A., Nogami, M., Yokozeki, T., Yamazaki, M., Nakamura, H., Watanabe, H., Kawamoto, K., Nakayama, K., Morris, A.J., Frohman, M.A., Kanaho, Y. Cell (1999) [Pubmed]
  9. Regulation of PLC-mediated signalling in vivo by CDP-diacylglycerol synthase. Wu, L., Niemeyer, B., Colley, N., Socolich, M., Zuker, C.S. Nature (1995) [Pubmed]
  10. Involvement of Ral GTPase in v-Src-induced phospholipase D activation. Jiang, H., Luo, J.Q., Urano, T., Frankel, P., Lu, Z., Foster, D.A., Feig, L.A. Nature (1995) [Pubmed]
  11. Failure of phosphatidic acid to translocate Ca2+ across phosphatidylcholine membranes. Holmes, R.P., Yoss, N.L. Nature (1983) [Pubmed]
  12. Serine phospholipid-specific phospholipase A that is secreted from activated platelets. A new member of the lipase family. Sato, T., Aoki, J., Nagai, Y., Dohmae, N., Takio, K., Doi, T., Arai, H., Inoue, K. J. Biol. Chem. (1997) [Pubmed]
  13. Phosphatidic acid and lysophosphatidic acid induce haptotactic migration of human monocytes. Zhou, D., Luini, W., Bernasconi, S., Diomede, L., Salmona, M., Mantovani, A., Sozzani, S. J. Biol. Chem. (1995) [Pubmed]
  14. Cholinergic stimulation of arachidonic acid and phosphatidic acid metabolism in C62B glioma cells. DeGeorge, J.J., Morell, P., McCarthy, K.D., Lapetina, E.G. J. Biol. Chem. (1986) [Pubmed]
  15. Involvement of a pertussis toxin-sensitive G protein in the mitogenic signaling pathways of sphingosine 1-phosphate. Goodemote, K.A., Mattie, M.E., Berger, A., Spiegel, S. J. Biol. Chem. (1995) [Pubmed]
  16. Stimulation of phosphatidic acid of calcium influx and cyclic GMP synthesis in neuroblastoma cells. Ohsako, S., Deguchi, T. J. Biol. Chem. (1981) [Pubmed]
  17. Phospholipase D: enzymology, mechanisms of regulation, and function. Exton, J.H. Physiol. Rev. (1997) [Pubmed]
  18. ADP-ribosylation factor, a small GTP-dependent regulatory protein, stimulates phospholipase D activity. Brown, H.A., Gutowski, S., Moomaw, C.R., Slaughter, C., Sternweis, P.C. Cell (1993) [Pubmed]
  19. Cytotoxicity of short-chain alcohols. Baker, R.C., Kramer, R.E. Annu. Rev. Pharmacol. Toxicol. (1999) [Pubmed]
  20. Acyl-phosphates initiate membrane phospholipid synthesis in Gram-positive pathogens. Lu, Y.J., Zhang, Y.M., Grimes, K.D., Qi, J., Lee, R.E., Rock, C.O. Mol. Cell (2006) [Pubmed]
  21. Phospholipase D and cell signaling. Billah, M.M. Curr. Opin. Immunol. (1993) [Pubmed]
  22. Stimulus-secretion coupling in rabbit neutrophils is not mediated by phosphatidylinositol breakdown. Cockcroft, S., Bennett, J.P., Gomperts, B.D. Nature (1980) [Pubmed]
  23. Lipid regulators of membrane traffic through the Golgi complex. Roth, M.G. Trends Cell Biol. (1999) [Pubmed]
  24. Phospholipase D activation in human natural killer cells through the Kp43 and CD16 surface antigens takes place by different mechanisms. Involvement of the phospholipase D pathway in tumor necrosis factor alpha synthesis. Balboa, M.A., Balsinde, J., Aramburu, J., Mollinedo, F., López-Botet, M. J. Exp. Med. (1992) [Pubmed]
  25. Myotonic muscular dystrophy: defective phospholipid metabolism in the erythrocyte plasma membrane. Grey, J.E., Gitelman, H.J., Roses, A.D. J. Clin. Invest. (1980) [Pubmed]
  26. Phospholipase D-modified low density lipoprotein is taken up by macrophages at increased rate. A possible role for phosphatidic acid. Aviram, M., Maor, I. J. Clin. Invest. (1993) [Pubmed]
  27. Regulation of Ras-GAP and the neurofibromatosis-1 gene product by eicosanoids. Han, J.W., McCormick, F., Macara, I.G. Science (1991) [Pubmed]
  28. Interleukin 4 receptor signaling in human monocytes and U937 cells involves the activation of a phosphatidylcholine-specific phospholipase C: a comparison with chemotactic peptide, FMLP, phospholipase D, and sphingomyelinase. Ho, J.L., Zhu, B., He, S., Du, B., Rothman, R. J. Exp. Med. (1994) [Pubmed]
  29. Involvement of a phospholipase D in the mechanism of action of granulocyte-macrophage colony-stimulating factor (GM-CSF): priming of human neutrophils in vitro with GM-CSF is associated with accumulation of phosphatidic acid and diradylglycerol. Bourgoin, S., Plante, E., Gaudry, M., Naccache, P.H., Borgeat, P., Poubelle, P.E. J. Exp. Med. (1990) [Pubmed]
  30. Effects of glucose on sorbitol pathway activation, cellular redox, and metabolism of myo-inositol, phosphoinositide, and diacylglycerol in cultured human retinal pigment epithelial cells. Thomas, T.P., Porcellati, F., Kato, K., Stevens, M.J., Sherman, W.R., Greene, D.A. J. Clin. Invest. (1994) [Pubmed]
  31. The GTPase stimulatory activities of the neurofibromatosis type 1 and the yeast IRA2 proteins are inhibited by arachidonic acid. Golubić, M., Tanaka, K., Dobrowolski, S., Wood, D., Tsai, M.H., Marshall, M., Tamanoi, F., Stacey, D.W. EMBO J. (1991) [Pubmed]
  32. Phospholipase D activity is required for suppression of yeast phosphatidylinositol transfer protein defects. Xie, Z., Fang, M., Rivas, M.P., Faulkner, A.J., Sternweis, P.C., Engebrecht, J.A., Bankaitis, V.A. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  33. Phospholipase D alpha 1-derived phosphatidic acid interacts with ABI1 phosphatase 2C and regulates abscisic acid signaling. Zhang, W., Qin, C., Zhao, J., Wang, X. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  34. Regulation of neurite outgrowth in N1E-115 cells through PDZ-mediated recruitment of diacylglycerol kinase zeta. Yakubchyk, Y., Abramovici, H., Maillet, J.C., Daher, E., Obagi, C., Parks, R.J., Topham, M.K., Gee, S.H. Mol. Cell. Biol. (2005) [Pubmed]
  35. Phospholipase D prevents etoposide-induced apoptosis by inhibiting the expression of early growth response-1 and phosphatase and tensin homologue deleted on chromosome 10. Kim, J., Lee, Y.H., Kwon, T.K., Chang, J.S., Chung, K.C., Min, d.o. .S. Cancer Res. (2006) [Pubmed]
  36. Evidence of lung surfactant abnormality in respiratory failure. Study of bronchoalveolar lavage phospholipids, surface activity, phospholipase activity, and plasma myoinositol. Hallman, M., Spragg, R., Harrell, J.H., Moser, K.M., Gluck, L. J. Clin. Invest. (1982) [Pubmed]
  37. Monoclonal anti-DNA IgM kappa in neuropathy binds to myelin and to a conformational epitope formed by phosphatidic acid and gangliosides. Freddo, L., Hays, A.P., Nickerson, K.G., Spatz, L., McGinnis, S., Lieberson, R., Vedeler, C.A., Shy, M.E., Autilio-Gambetti, L., Grauss, F.C. J. Immunol. (1986) [Pubmed]
  38. Phosphorylation of rat liver nuclear envelopes. II. Characterization of in vitro lipid phosphorylation. Smith, C.D., Wells, W.W. J. Biol. Chem. (1983) [Pubmed]
  39. Exercise-induced translocation of protein kinase C and production of diacylglycerol and phosphatidic acid in rat skeletal muscle in vivo. Relationship to changes in glucose transport. Cleland, P.J., Appleby, G.J., Rattigan, S., Clark, M.G. J. Biol. Chem. (1989) [Pubmed]
  40. Stimulation of Na+-Ca2+ exchange in cardiac sarcolemmal vesicles by phospholipase D. Philipson, K.D., Nishimoto, A.Y. J. Biol. Chem. (1984) [Pubmed]
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