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Chemical Compound Review

AC1O5OI3     2-[[(E,2R,3S)-2-amino-3- hydroxy-octadec-4...

Synonyms: 10216-23-6, Sphingosylphosphocholine, Sphingosine phosphorylcholine
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Disease relevance of 2-[[(E,2R,3S)-2-amino-3-hydroxy-octadec-4-enoxy]-hydroxy-phosphoryl]oxyethyl-trimethyl-azanium


Psychiatry related information on 2-[[(E,2R,3S)-2-amino-3-hydroxy-octadec-4-enoxy]-hydroxy-phosphoryl]oxyethyl-trimethyl-azanium


High impact information on 2-[[(E,2R,3S)-2-amino-3-hydroxy-octadec-4-enoxy]-hydroxy-phosphoryl]oxyethyl-trimethyl-azanium


Biological context of 2-[[(E,2R,3S)-2-amino-3-hydroxy-octadec-4-enoxy]-hydroxy-phosphoryl]oxyethyl-trimethyl-azanium


Anatomical context of 2-[[(E,2R,3S)-2-amino-3-hydroxy-octadec-4-enoxy]-hydroxy-phosphoryl]oxyethyl-trimethyl-azanium


Associations of 2-[[(E,2R,3S)-2-amino-3-hydroxy-octadec-4-enoxy]-hydroxy-phosphoryl]oxyethyl-trimethyl-azanium with other chemical compounds


Gene context of 2-[[(E,2R,3S)-2-amino-3-hydroxy-octadec-4-enoxy]-hydroxy-phosphoryl]oxyethyl-trimethyl-azanium

  • The mRNA of Scamper, a putative intracellular calcium channel activated by sphingosylphosphocholine, contains a long 5' transcript leader with several upstream AUGs [17].
  • Lysosphingomyelin has been implicated in the nervous system involvement associated with type A disease in humans and accumulations of the NPC-1 protein and apolipoprotein D have been found in murine NP-C brain [18].

Analytical, diagnostic and therapeutic context of 2-[[(E,2R,3S)-2-amino-3-hydroxy-octadec-4-enoxy]-hydroxy-phosphoryl]oxyethyl-trimethyl-azanium


  1. Sphingosylphosphocholine, a signaling molecule which accumulates in Niemann-Pick disease type A, stimulates DNA-binding activity of the transcription activator protein AP-1. Berger, A., Rosenthal, D., Spiegel, S. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
  2. Preparation of a naturally occurring D-erythro-(2S, 3R)-sphingosylphosphocholine using Shewanella alga NS-589. Sueyoshi, N., Izu, H., Ito, M. J. Lipid Res. (1997) [Pubmed]
  3. Metabolism and neurite promoting effect of exogenous sphingosylphosphocholine in cultured murine neuroblastoma cells. Sugiyama, E., Uemura, K., Hara, A., Taketomi, T. J. Biochem. (1993) [Pubmed]
  4. Sphingosylphosphorylcholine in Niemann-Pick disease brain: accumulation in type A but not in type B. Rodriguez-Lafrasse, C., Vanier, M.T. Neurochem. Res. (1999) [Pubmed]
  5. Lysosphingomyelin prevents behavioral aberrations and hippocampal neuron loss induced by the metabotropic glutamate receptor agonist quisqualate. Hodgson, D.M., Taylor, A.N., Zhang, Z., Rosenberg, A. Prog. Neuropsychopharmacol. Biol. Psychiatry (1999) [Pubmed]
  6. A novel membrane receptor with high affinity for lysosphingomyelin and sphingosine 1-phosphate in atrial myocytes. Bünemann, M., Liliom, K., Brandts, B.K., Pott, L., Tseng, J.L., Desiderio, D.M., Sun, G., Miller, D., Tigyi, G. EMBO J. (1996) [Pubmed]
  7. Sphingosylphosphocholine reduces the calcium ion requirement for activating tissue transglutaminase. Lai, T.S., Bielawska, A., Peoples, K.A., Hannun, Y.A., Greenberg, C.S. J. Biol. Chem. (1997) [Pubmed]
  8. Characteristics and partial purification of a novel cytosolic, magnesium-independent, neutral sphingomyelinase activated in the early signal transduction of 1 alpha,25-dihydroxyvitamin D3-induced HL-60 cell differentiation. Okazaki, T., Bielawska, A., Domae, N., Bell, R.M., Hannun, Y.A. J. Biol. Chem. (1994) [Pubmed]
  9. Re-evaluation of primary structure, topology, and localization of Scamper, a putative intracellular Ca2+ channel activated by sphingosylphosphocholine. Schnurbus, R., de Pietri Tonelli, D., Grohovaz, F., Zacchetti, D. Biochem. J. (2002) [Pubmed]
  10. Partial synthesis and properties of a series of N-acyl sphingomyelins. Sripada, P.K., Maulik, P.R., Hamilton, J.A., Shipley, G.G. J. Lipid Res. (1987) [Pubmed]
  11. A new wound healing agent--sphingosylphosphorylcholine. Sun, L., Xu, L., Henry, F.A., Spiegel, S., Nielsen, T.B. J. Invest. Dermatol. (1996) [Pubmed]
  12. The potent lipid mitogen sphingosylphosphocholine activates the DNA binding activity of upstream stimulating factor (USF), a basic helix-loop-helix-zipper protein. Berger, A., Cultaro, C.M., Segal, S., Spiegel, S. Biochim. Biophys. Acta (1998) [Pubmed]
  13. Sphingosylphosphocholine modulates the ryanodine receptor/calcium-release channel of cardiac sarcoplasmic reticulum membranes. Betto, R., Teresi, A., Turcato, F., Salviati, G., Sabbadini, R.A., Krown, K., Glembotski, C.C., Kindman, L.A., Dettbarn, C., Pereon, Y., Yasui, K., Palade, P.T. Biochem. J. (1997) [Pubmed]
  14. Sphingosylphosphocholine is a naturally occurring lipid mediator in blood plasma: a possible role in regulating cardiac function via sphingolipid receptors. Liliom, K., Sun, G., Bünemann, M., Virág, T., Nusser, N., Baker, D.L., Wang, D.A., Fabian, M.J., Brandts, B., Bender, K., Eickel, A., Malik, K.U., Miller, D.D., Desiderio, D.M., Tigyi, G., Pott, L. Biochem. J. (2001) [Pubmed]
  15. Effects of various lysosphingolipids on cell growth, morphology and lipid composition in three neuroblastoma cell lines. Sugiyama, E., Uemura, K., Hara, A., Taketomi, T. Biochem. Biophys. Res. Commun. (1990) [Pubmed]
  16. Lysosphingomyelin-elicited Ca2+ mobilization from rat brain microsomes. Furuya, S., Kurono, S., Hirabayashi, Y. Journal of lipid mediators and cell signalling. (1996) [Pubmed]
  17. Translational control of Scamper expression via a cell-specific internal ribosome entry site. De Pietri Tonelli, D., Mihailovich, M., Schnurbus, R., Pesole, G., Grohovaz, F., Zacchetti, D. Nucleic Acids Res. (2003) [Pubmed]
  18. Niemann-Pick disease. Kolodny, E.H. Curr. Opin. Hematol. (2000) [Pubmed]
  19. Human placental sphingomyelinase. Purification to homogeneity, antigenic properties and partial amino-acid sequences of the enzyme. Kurth, J., Stoffel, W. Biol. Chem. Hoppe-Seyler (1991) [Pubmed]
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