LIPID MAPS

Structure Database (LMSD)

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Common Name

Sphingosine-1-phosphocholine

Systematic Name

Sphing-4-enine-1-phosphocholine

Synonyms

SM(d18:1/0:0)

LM ID

LMSP01060001

Formula

C₂₃H₄₉N₂O₅P

Exact Mass

Calculate m/z

464.337911

Sum Composition

LSM 18:1;O2

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

D-erythro Lysosphingomyelin is a bioactive sphingolipid.¹ It is an agonist of sphingosine-1-phosphate receptor 1 (S1P1), S1P2, and S1P3 (EC50s = 167.7, 368.1, and 482.6 nM, respectively, for the human receptors). D-erythro Lysosphingomyelin is also an agonist of the orphan receptor ovarian cancer G protein-coupled receptor 1 (ORG1) that induces calcium accumulation in cells overexpressing OGR1 (EC50 = ~35 nM).² Levels of D-erythro lysosphingomyelin are increased in skin isolated from patients with atopic dermatitis, as well as postmortem brain from patients with Niemann-Pick disease type A, but not type B.^3,4 As this product is derived from a natural source, there may be variations in the sphingoid backbone. [Matreya, LLC. Catalog No. 1318]

This information has been provided by Cayman Chemical

References

1. Nixon, G.F., Mathieson, F.A., and Hunter, I. The multi-functional role of sphingosylphosphorylcholine. Prog. Lipid Res. 47(1), 62-75 (2008).

2. Im, D.-S., Clemens, J., Macdonald, T.L., et al. Characterization of the human and mouse sphingosine 1-phosphate receptor, S1P5 (Edg-8): Structure-activity relationship of sphingosine1-phosphate receptors. Biochemistry 40(46), 14053-14060 (2001).

3. Meyer zu Heringdorf, D., Himmel, H.M., and Jakobs, K.H. Sphingosylphosphorylcholine-biological functions and mechanisms of action. Biochim. Biophys. Acta 1582(1-3), 178-189 (2002).

4. Rodriguez-Lafrasse, C., and Vanier, M.T. Sphingosylphosphorylcholine in Niemann-Pick disease brain: Accumulation in type A but not in type B. Neurochem. Res. 24(2), 199-205 (1999).

String Representations

InChiKey (Click to copy)

JLVSPVFPBBFMBE-HXSWCURESA-N

InChi (Click to copy)

InChI=1S/C23H49N2O5P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(26)22(24)21-30-31(27,28)29-20-19-25(2,3)4/h17-18,22-23,26H,5-16,19-21,24H2,1-4H3/b18-17+/t22-,23+/m0/s1

SMILES (Click to copy)

[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(N)[C@]([H])(O)/C=C/CCCCCCCCCCCCC