LIPID MAPS

Structure Database (LMSD)

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Common Name

Cer(d18:1/26:0)

Systematic Name

N-(hexacosanoyl)-sphing-4-enine

Synonyms

C26 Cer
N-(hexacosanoyl)-ceramide
N-(hexacosanoyl)-ceramide
Cer[NS]

LM ID

LMSP02010011

Formula

C₄₄H₈₇NO₃

Exact Mass

Calculate m/z

677.668595

Sum Composition

Cer 44:1;O2

Abbrev Chains

Cer 18:1;O2/26:0

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Predict MS/MS spectrum ([M-H]-)

Classification

Biological Context

C26 Ceramide is an endogenous ceramide.¹ C26 Ceramide levels are increased in tumor tissues from patients with hepatocellular carcinoma (HCC) compared to normal liver tissues.² C26 ceramide levels are also increased in acid ceramidase deficiency, a lysosomal disorder characterized by developmental delay, myoclonic seizures, and hematological abnormalities.³ This product is fully synthetic and has no variations in the fatty acyl chain or sphingoid backbone.

This information has been provided by Cayman Chemical

References

1. Shin, K.-O., Kim, S., Park, B.D., et al. N-Palmitoyl serinol stimulates ceramide production through a CB1-dependent mechanism in in vitro model of skin inflammation. Int. J. Mol. Sci. 22(15), 8302 (2021).

2. Miura, K., Nagahashi, M., Prasoon, P., et al. Dysregulation of sphingolipid metabolic enzymes leads to high levels of sphingosine-1-phosphate and ceramide in human hepatocellular carcinoma. Hepatol. Res. 51(5), 614-626 (2021).

3. Mahmoud, I.G., Elmonem, M.A., Zaki, M.S., et al. ASAH1-related disorders: Description of 15 novel pediatric patients and expansion of the clinical phenotype. Clin. Genet. 98(6), 598-605 (2020).

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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)

CJROVRTUSFQVMR-GVOPMEMSSA-N

InChi (Click to copy)

InChI=1S/C44H87NO3/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-26-28-30-32-34-36-38-40-44(48)45-42(41-46)43(47)39-37-35-33-31-29-27-16-14-12-10-8-6-4-2/h37,39,42-43,46-47H,3-36,38,40-41H2,1-2H3,(H,45,48)/b39-37+/t42-,43+/m0/s1

SMILES (Click to copy)

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