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Structure Database (LMSD)

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Common Name

Cer(t18:0/18:0)

Systematic Name

N-(octadecanoyl)-4R-hydroxysphinganine

Synonyms

N-(octadecanoyl)-phytoceramide
N-(stearoyl)-phytoceramide
Cer[NP]

LM ID

LMSP02030006

Formula

C₃₆H₇₃NO₄

Exact Mass

Calculate m/z

583.553959

Sum Composition

Cer 36:0;O3

Abbrev Chains

Cer 18:0;O3/18:0

Status

Curated

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Classification

Biological Context

C18 Phytoceramide (t18:0/18:0) (Cer(t18:0/18:0)) is a bioactive sphingolipid found in S. cerevisiae, wheat grains, and the stratum corneum layer of mammalian epidermis.^1,2,3,4 Cer(t18:0/18:0) is composed of a phytosphingosine backbone amine-linked to a C18 fatty acid chain. Cer(t18:0/18:0) has a role in regulation of apoptosis, cell differentiation, proliferation of smooth muscle cells, and inhibition of the mitochondrial respiratory chain.^5,6,7 It also inhibits expression of the allergic cytokines IL-4, TNF-α, and transcription factors c-Jun and NF-κB in histone-stimulated murine skin tissue.¹ Formulations containing cer(t18:0/18:0) have been used used in cosmetics as a skin protectants as they reduce water loss to prevent epidermal dehydration and irritation.^2,3 [Matreya, LLC. Catalog No. 2034]

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

3. 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).

4. Ryu, K.-R., Lee, B., Lee, I.-A., et al. Anti-scratching behavioral effects of N-stearoyl-phytosphingosine and 4-hydroxysphinganine in mice. Lipids 45(7), 613-618 (2010).

5. Huang, H.-C., and Chang, T.-M. Ceramide 1 and ceramide 3 act synergistically on skin hydration and the transepidermal water loss of sodium lauryl sulfate-irritated skin. Int. J. Dermatol. 47(8), 812-819 (2008).

6. Corcoran, C., and Hendry, J. Ceramide cosmetic compositions. (1994).

7. Bizot-Foulon, V., Godeau, G., Guessous, F., et al. Inhibition of human neutrophil elastase by wheat ceramides. Int. J. Cosmet. Sci. 17(6), 255-264 (1995).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Saccharomyces cerevisiae (#4932)

Saccharomycetes (#4891)

Mass spectrometry-based profiling of phospholipids and sphingolipids in extracts from Saccharomyces cerevisiae.,
Yeast, 2006

Pubmed ID: 16652392

String Representations

InChiKey (Click to copy)

IEZRNEGTKRQRFV-LFBNJJMOSA-N

InChi (Click to copy)

InChI=1S/C36H73NO4/c1-3-5-7-9-11-13-15-17-18-19-21-23-25-27-29-31-35(40)37-33(32-38)36(41)34(39)30-28-26-24-22-20-16-14-12-10-8-6-4-2/h33-34,36,38-39,41H,3-32H2,1-2H3,(H,37,40)/t33-,34+,36-/m0/s1

SMILES (Click to copy)

[C@](CO)([H])(NC(CCCCCCCCCCCCCCCCC)=O)[C@]([H])(O)[C@H](O)CCCCCCCCCCCCCC