LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG

Common Name

SM(d18:1/16:0)

Systematic Name

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

Synonyms

C16 Sphingomyelin

LM ID

LMSP03010003

Formula

C₃₉H₇₉N₂O₆P

Exact Mass

Calculate m/z

702.567576

Sum Composition

SM 34:1;O2

Abbrev Chains

SM 18:1;O2/16:0

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

C16 Sphingomyelin is a naturally occurring sphingolipid.^1,2,3 Levels of C16 sphingomyelin are elevated in the prefrontal cortex and cerebellum in a rat model of diabetes induced by streptozotocin (STZ), as well as in the liver in mouse models of Niemann-Pick type C1 disease.^1,2 Plasma levels of C16 sphingomyelin are decreased in patients with prostate cancer.³ Model membranes containing C16 sphingomyelin, 1-palmitoyl-2-oleoyl-sn-glycero-3-PC (POPC), and cholesterol have been used in the study of lipid raft dynamics and membrane organization.^4,5

This information has been provided by Cayman Chemical

References

1. 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).

2. 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).

3. 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).

4. de Almeida, R.F.M., Loura, L.M.S., Fedorov, A., et al. Lipid rafts have different sizes depending on membrane composition: A time-resolved fluorescence resonance energy transfer study. J. Mol. Biol. 346(4), 1109-1120 (2005).

5. Halling, K.K., Ramstedt, B., Nyström, J.H., et al. Cholesterol interactions with fluid-phase phospholipids: Effect on the lateral organization of the bilayer. Biophys. J. 95(8), 3861-3871 (2008).

Reactions

Filter by species:

Click on an edge to display the reaction(s).

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)

RWKUXQNLWDTSLO-GWQJGLRPSA-N

InChi (Click to copy)

InChI=1S/C39H79N2O6P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-38(42)37(36-47-48(44,45)46-35-34-41(3,4)5)40-39(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h30,32,37-38,42H,6-29,31,33-36H2,1-5H3,(H-,40,43,44,45)/b32-30+/t37-,38+/m0/s1

SMILES (Click to copy)

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