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Structure Database (LMSD)

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Common Name

Cer(d18:1/2:0)

Systematic Name

N-(acetyl)-sphing-4-enine

Synonyms

C2-ceramide
N-(acetyl)-ceramide
N-(acetyl)-ceramide
N-acetylsphingosine
Cer[NS]

LM ID

LMSP02010014

Formula

C₂₀H₃₉NO₃

Exact Mass

Calculate m/z

341.292994

Sum Composition

Cer 20:1;O2

Abbrev Chains

Cer 18:1;O2/2:0

Status

Curated

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Classification

Biological Context

C2 ceramide is a cell-permeable analog of naturally occurring ceramides. It mediates many diverse biological activities, as do natural ceramides. These processes include differentiation of HL-60 cells,1 induction of apoptosis,2 activation of protein phosphatase 2A,3 and inhibition of the mitochondrial respiratory chain.⁴ C2 ceramide also enhances the expression of COX-2 in human dermal fibroblasts5 and stimulates the growth of bovine aortic smooth muscle cells.⁶ The ability of C2 ceramide to destabilize membranes may be responsible for its inhibition of platelet aggregation.⁷

This information has been provided by Cayman Chemical

References

1. Obeid, L.M., Linardic, C.M., Karolak, L.A., et al. Programmed cell death induced by ceramide. Science 259, 1769-1771 (1993).

2. Okazaki, T., Bielawska, A., Bell, R.M., et al. Role of ceramide as a lipid mediator of 1α,25-dihydroxyvitamin D3-induced HL-60 cell differentiation. The Journal of Biological Chemisty 265, 15823-15831 (1990).

3. Dobrowsky, R.T., Kamibayashi, C., Mumby, M.C., et al. Ceramide activates heterotrimeric protein phosphatase 2A. The Journal of Biological Chemisty 268(21), 15523-15530 (1993).

4. Ballou, L.R., Chao, C.P., Holness, M.A., et al. Interleukin-1-mediated PGE2 production and sphingomyelin metabolism. Evidence for the regulation of cyclooxygenase gene expression by sphingosine and ceramide. The Journal of Biological Chemisty 267, 20044-20050 (1992).

5. 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).

6. 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).

7. Simon, C.G., Jr., and Gear, A.R.L. Membrane-destabilizing properties of C2-ceramide may be responsible for its ability to inhibit platelet aggregation. Biochemistry 37, 2059-2069 (1998).

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String Representations

InChiKey (Click to copy)

BLTCBVOJNNKFKC-QUDYQQOWSA-N

InChi (Click to copy)

InChI=1S/C20H39NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20(24)19(17-22)21-18(2)23/h15-16,19-20,22,24H,3-14,17H2,1-2H3,(H,21,23)/b16-15+/t19-,20+/m0/s1

SMILES (Click to copy)

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