LIPID MAPS

Structure Database (LMSD)

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Common Name

Sphingosine

Systematic Name

Sphing-4-enine

Synonyms

Sphingosine
4-Sphingenine
D-erythro-Sphingosine
(2S,3R,4E)-2-Amino-4-octadecene-1,3-diol
4-trans-Sphingenine
Sphingenine
2S-Amino-4E-octadecene-1,3R-diol

LM ID

LMSP01010001

Formula

C₁₈H₃₇NO₂

Exact Mass

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299.282429

Sum Composition

SPB 18:1;O2

Status

Curated

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Classification

Biological Context

Sphingosine (d18:1) is formed primarily from the breakdown of ceramide.¹ Sphingosine inhibits protein kinase C and phosphatidic acid phosphohydrolase, whereas it activates phospholipase D and diacylglycerol (DAG) kinase.¹ Phosphorylation of sphingosine by sphingosine kinases 1 and 2 (SPHK 1, SPHK 2) produces sphingosine-1-phosphate, a potent bioactive lipid that exhibits a broad spectrum of biological activities including cell proliferation, survival, migration, cytoskeletal organization, and morphogenesis.^2,3,4

This information has been provided by Cayman Chemical

References

1. Kluk, M.J., and Hla, T. Signaling of sphingosine-1-phosphate via the S1P/EDG-family of G-protein-coupled receptors. Biochim. Biophys. Acta 1582(1-3), 72-80 (2002).

2. Takuwa, Y., Takuwa, N., and Sugimoto, N. The Edg family G protein-coupled receptors for lysophospholipids: Their signaling properties and biological activities. J. Biochem. 131(6), 767-771 (2002).

3. Ishii, I., Fukushima, N., Ye, X., et al. Lysophospholipid receptors: Signaling and biology. Annu. Rev. Biochem. 73, 321-354 (2004).

4. Hannun, Y.A., Luberto, C., and Argraves, K.M. Enzymes of sphingolipid metabolism: From modular to integrative signaling. Biochemistry 40(16), 4893-4903 (2001).