LIPID MAPS

Structure Database (LMSD)

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Common Name

SM(d18:1/20:0)

Systematic Name

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

Synonyms

C20 Sphingomyelin

LM ID

LMSP03010005

Formula

C₄₃H₈₇N₂O₆P

Exact Mass

Calculate m/z

758.630176

Sum Composition

SM 38:1;O2

Abbrev Chains

SM 18:1;O2/20:0

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

C20 Sphingomyelin is a naturally occurring sphingolipid.^1,2,3,4 Levels of C20 sphingomyelin are upregulated in the hippocampus of rats with diabetes induced by streptozotocin and in human plasma where it is positively correlated with insulin resistance in obese humans.² C20 sphingomyelin is also upregulated in the liver of a mouse model of Niemann-Pick type C1 disease, a neurodegenerative cholesterol-sphingolipid lysosomal storage disorder.¹ The plasma concentration of C20 sphingomyelin is decreased in men with prostate cancer.³ As this product is derived from a natural source, there may be variations in the sphingoid backbone. [Matreya, LLC. Catalog No. 1917]

This information has been provided by Cayman Chemical

References

1. Hanamatsu, H., Ohnishi, S., Sakai, S., et al. Altered levels of serum sphingomyelin and ceramide containing distinct acyl chains in young obese adults. Nutr. Diabetes 4(10), e141 (2014).

2. Awwad, H.M., Ohlmann, C.H., Stoeckle, M., et al. Choline-phospholipids inter-conversion is altered in elderly patients with prostate cancer. Biochimie 126, 108-114 (2016).

3. Fiedorowicz, A., Prokopiuk, S., Zendzian-Piotrowska, M., et al. Sphingolipid profiles are altered in prefrontal cortex of rats under acute hyperglycemia. Neuroscience 256, 282-291 (2014).

4. Praggastis, M., Tortelli, B., Zhang, J., et al. A murine Niemann-Pick C1 I1061T knock-in model recapitulates the pathological features of the most prevalent human disease allele. J. Neurosci. 35(21), 8091-8106 (2015).

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References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010

Pubmed ID: 20671299

DOI: 10.1194/jlr.M009449

String Representations

InChiKey (Click to copy)

AADLTHQNYQJHQV-SVLGDMRNSA-N

InChi (Click to copy)

InChI=1S/C43H87N2O6P/c1-6-8-10-12-14-16-18-20-21-22-23-25-27-29-31-33-35-37-43(47)44-41(40-51-52(48,49)50-39-38-45(3,4)5)42(46)36-34-32-30-28-26-24-19-17-15-13-11-9-7-2/h34,36,41-42,46H,6-33,35,37-40H2,1-5H3,(H-,44,47,48,49)/b36-34+/t41-,42+/m0/s1

SMILES (Click to copy)

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