LIPID MAPS

Structure Database (LMSD)

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Common Name

SM(d18:1/26:0)

Systematic Name

N-(hexacosanoyl)-sphing-4-enine-1-phosphocholine

Synonyms

C26 Sphingomyelin

LM ID

LMSP03010010

Formula

C₄₉H₉₉N₂O₆P

Exact Mass

Calculate m/z

842.724076

Sum Composition

SM 44:1;O2

Abbrev Chains

SM 18:1;O2/26:0

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

C26 Sphingomyelin is a sphingolipid that has been found in serum and cell or brain extracts.^1,2,3 C26 sphingomyelin levels are increased in the serum of patients with hemophagocytic lymphohistiocytosis, an inflammatory condition characterized by excessive immune activation.³ C26 sphingomyelin has been used a component of monolayers to study the influence of sphingomyelin acyl chain length on sphingomyelin-sterol interactions.⁴ [Matreya, LLC. Catalog No. 2137]

This information has been provided by Cayman Chemical

References

1. Li, X.M., Momsen, M.M., Brockman, H.L., et al. Sterol structure and sphingomyelin acyl chain length modulate lateral packing elasticity and detergent solubility in model membranes. Biophys. J. 85(6), 3788-3801 (2003).

2. Jenkins, R.W., Clarke, C.J., Lucas, J.T., Jr., et al. Evaluation of the role of secretory sphingomyelinase and bioactive sphingolipids as biomarkers in hemophagocytic lymphohistiocytosis. Am. J. Hematol. 88(11), E265-E272 (2013).

3. Willmann, J., Mahlstedt, K., Leibfritz, D., et al. Characterization of sphingomyelins in lipid extracts using a HPLC-MS-offline-NMR method. Anal. Chem. 79(11), 4188-4191 (2007).

4. Wang, J.-R., Zhang, H., Yau, L.D., et al. Improved sphingolipidomic approach based on ultra-high performance liquid chromatography and multiple mass spectrometries with application to cellular neurotoxicity. Anal. Chem. 86(12), 5688-5696 (2014).

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References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Mus musculus (#10090)

Mammalia (#40674)

Subcellular organelle lipidomics in TLR-4-activated macrophages.,
J Lipid Res, 2010

Pubmed ID: 20574076

DOI: 10.1194/jlr.M008748

String Representations

InChiKey (Click to copy)

VRAWSAPVSSLIRI-MVUJCARGSA-N

InChi (Click to copy)

InChI=1S/C49H99N2O6P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-26-27-28-29-31-33-35-37-39-41-43-49(53)50-47(46-57-58(54,55)56-45-44-51(3,4)5)48(52)42-40-38-36-34-32-30-19-17-15-13-11-9-7-2/h40,42,47-48,52H,6-39,41,43-46H2,1-5H3,(H-,50,53,54,55)/b42-40+/t47-,48+/m0/s1

SMILES (Click to copy)

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