A bioactive sphingolipid
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D-erythro Lysosphingomyelin (d18:1)

Item No. 10007947

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[[[[2S-amino-3R-hydroxy-4E-octadecenyl]oxy]hydroxyphosphinyl]oxy]-N,N,N-trimethyl-ethanaminium
CAS Number
1670-26-4
Synonyms
  • D-erythro Lyso SM(18:1)
  • D-erythro-Sphingophosphorylcholine
  • D-erythro Sphingosine-1-Phosphocholine (d18:1)
  • Lyso-SM(d18:1)
  • Lysosphingomyelin (d18:1)
Molecular Formula
C23H49N2O5P
Formula Weight
464.6
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
Ethanol: 15 mg/mlPBS (pH 7.2): 5 mg/ml
SMILES
CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)COP([O-])(OCC[N+](C)(C)C)=O
InChi Code
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
InChi Key
JLVSPVFPBBFMBE-HXSWCURESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    25 mg

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    Product Description

    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]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

    2. 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).

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

    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).