LIPID MAPS

Structure Database (LMSD)

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Common Name

Cer(d18:0/18:0)

Systematic Name

N-(octadecanoyl)-sphinganine

Synonyms

C18DH Cer
N-(octadecanoyl)-dihydroceramide
N-(stearoyl)-dihydroceramide
Cer[NdS]

LM ID

LMSP02020008

Formula

C₃₆H₇₃NO₃

Exact Mass

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567.559044

Sum Composition

Cer 36:0;O2

Abbrev Chains

Cer 18:0;O2/18:0

Status

Curated

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Classification

Biological Context

C18 dihydro Ceramide is a bioactive sphingolipid and precursor in the de novo synthesis of C18 ceramide that lacks the 4,5-trans double bond.¹ Increased C18 dihydroceramide lipid levels lead to increased triacylglycerol storage and autophagosome accumulation as well as upregulation of the fibrosis markers α-SMA and FGF2 in Chang and LX-2 liver cells. C18 dihydro Ceramide is elevated in the plasma of pre-diabetics up to 9 years prior to the onset of type 2 diabetes.² It is also elevated in the skin of patients with lesional atopic dermatitis.³

This information has been provided by Cayman Chemical

References

1. Joo, J.-M., Hwang, J.-H., Bae, S., et al. Relationship of ceramide-, and free fatty acid-cholesterol ratios in the stratum corneum with skin barrier function of normal, atopic dermatitis lesional and non-lesional skins. J. Dermatol. Sci. 77(1), 71-74 (2015).

2. Lee, A.Y., Lee, J.W., Kim, J.-E., et al. Dihydroceramide is a key metabolite that regulates autophagy and promotes fibrosis in hepatic steatosis model. Biochem. Biophys. Res. Commun. 494(3-4), 460-469 (2017).

3. Wigger, L., Cruciani-Guglielmacci, C., Nicolas, A., et al. Plasma dihydroceramides are diabetes susceptibility biomarker candidates in mice and humans. Cell Rep. 18(9), 2269-2279 (2017).

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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)

KZTJQXAANJHSCE-OIDHKYIRSA-N

InChi (Click to copy)

InChI=1S/C36H73NO3/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-36(40)37-34(33-38)35(39)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h34-35,38-39H,3-33H2,1-2H3,(H,37,40)/t34-,35+/m0/s1

SMILES (Click to copy)

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