LIPID MAPS

Structure Database (LMSD)

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Common Name

Cer(d18:1/24:1(15Z))

Systematic Name

N-(15Z-tetracosenoyl)-sphing-4-enine

Synonyms

C24:1 Cer
N-(15Z-tetracosenoyl)-ceramide
N-(15Z-tetracosenoyl)-ceramide
N-nervonyl-sphingosine
Cer[NS]

LM ID

LMSP02010009

Formula

C₄₂H₈₁NO₃

Exact Mass

Calculate m/z

647.621644

Sum Composition

Cer 42:2;O2

Abbrev Chains

Cer 18:1;O2/24:1

Status

Curated

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Classification

Biological Context

C24:1 Ceramide (d18:1/24:1(15Z)) is one of the most abundant naturally occurring ceramides.^1,2,3 Ceramides mediate many diverse biological activities, as has been demonstrated in studies utilizing cell-permeable ceramide analogs. A few of the processes regulated by ceramides include apoptosis, cell differentiation, proliferation of smooth muscle cells, and inhibition of the mitochondrial respiratory chain.^4,5,6

This information has been provided by Cayman Chemical

References

1. Augé, N., Andrieu, N., Nègre-Salvayre, A., et al. The sphingomyelin-ceramide signaling pathway is involved in oxidized low density lipoprotein-induced cell proliferation. The Journal of Biological Chemisty 271(32), 19251-19255 (1996).

2. Gu, Q., Kerwin, J.L., Watts, J.D., et al. Ceramide profiling of complex lipid mixtures by electrospray ionization mass spectrometry. Anal. Biochem. 244(2), 347-356 (1997).

3. Testi, R. Sphingomyelin breakdown and cell fate. Trends Biochem. Sci. 21(12), 468-471 (1996).

4. Gudz, T.I., Tserng, K.Y., and Hoppel, C.L. Direct inhibition of mitochondrial respiratory chain complex III by cell-permeable ceramide. The Journal of Biological Chemisty 272(39), 24154-24158 (1997).

5. Krivit, W., and Hammarström, S. Identification and quantitation of free ceramides in human platelets. J. Lipid Res. 13(4), 525-530 (1972).

6. Clayton, R.B., Cooper, J.M., Curstedt, T., et al. Stimulation of erythroblast maturation in vitro by sphingolipids. J. Lipid Res. 15(6), 557-562 (1974).

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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

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)

VJSBNBBOSZJDKB-KPEYJIHVSA-N

InChi (Click to copy)

InChI=1S/C42H81NO3/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-42(46)43-40(39-44)41(45)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2/h17-18,35,37,40-41,44-45H,3-16,19-34,36,38-39H2,1-2H3,(H,43,46)/b18-17-,37-35+/t40-,41+/m0/s1

SMILES (Click to copy)

[C@](CO)([H])(NC(CCCCCCCCCCCCC/C=C\CCCCCCCC)=O)[C@]([H])(O)/C=C/CCCCCCCCCCCCC