D-erythro/L-threo Lysosphingomyelin (d18:1)

Lysosphingomyelin is an endogenous bioactive sphingolipid and a constituent of lipoproteins. It is produced by the removal of the acyl group from sphingomyelin by a deacylase and acts as a precursor in the biosynthesis of sphingosine-1-phosphate (S1P, Cay-62570). D-erythro Lysosphingomyelin is an agonist of the S1P receptors S1P1, S1P2, and S1P3 (EC50s = 167.7, 368.1, and 482.6 nM, respectively, for the human receptors). It 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). 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. L-threo lysosphingomyelin is also an S1P1-3 agonist (EC50s = 19.3, 131.8, and 313.3 nM, respectively). This product is a mixture of D-erythro and L-threo lysosphingomyelin. As this product is derived from a natural source, there may be variations in the sphingoid backbone. [Matreya, LLC. Catalog No. 1321]Formal Name: 2-[[[(2-amino-3-hydroxy-4-octadecen-1-yl)oxy]hydroxyphosphinyl]oxy]-N,N,N-trimethyl-ethanaminium, inner salt. CAS Number: 82970-80-7. Synonyms: D-erythro/L-threo Lyso SM(18:1), D-erythro/L-threo Sphingosine-1-Phosphocholine (d18:1), D-erythro/L-threo-Sphingosylphosphorylcholine. Molecular Formula: C23H49N2O5P. Formula Weight: 464.6. Purity: >98%. Formulation: (Request formulation change), A solid. Solubility: Chloroform:Methanol (2:1): soluble. SMILES: NC(COP(OCC[N+](C)(C)C)([O-])=O)C(O)/C=C/CCCCCCCCCCCCC. 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+. InChi Key: JLVSPVFPBBFMBE-ISLYRVAYSA-N.