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Structure Database (LMSD)

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Common Name

Cer(d18:1/14:0)

Systematic Name

N-(tetradecanoyl)-sphing-4-enine

Synonyms

C14 Cer
N-(tetradecanoyl)-ceramide
N-(myristoyl)-ceramide
Cer[NS]

LM ID

LMSP02010001

Formula

C₃₂H₆₃NO₃

Exact Mass

Calculate m/z

509.480794

Sum Composition

Cer 32:1;O2

Abbrev Chains

Cer 18:1;O2/14:0

Status

Curated

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Classification

Biological Context

C14 Ceramide is an endogenous ceramide generated by ceramide synthase 6.1 During nutrient-deprivation-induced necroptosis in MEF cells, C14 ceramide levels increase in a time-dependent manner.² C14 ceramide plasma levels were reduced in obese patients with or without diabetes following a 12-week supervised exercise training program, correlating positively with weight and fat loss and negatively with an increase in insulin sensitivity.³ In contrast, plasma levels were higher in Parkinson’s disease patients with dementia than those without dementia and higher levels were correlated with deficits in memory.⁴

This information has been provided by Cayman Chemical

References

1. Grosch, S., Schiffmann, S., and Geisslinger, G. Chain length-specific properties of ceramides. Prog. Lipid Res. 51(1), 50-62 (2012).

2. Kasumov, T., Solomon, T.P., Hwang, C., et al. Improved insulin sensitivity after exercise training is linked to reduced plasma C14:0 ceramide in obesity and type 2 diabetes. Obesity (Silver Spring) 23(7), 1414-1421 (2015).

3. Sundaram, K., Mather, A.R., Marimuthu, S., et al. Loss of neutral ceramidase protects cells from nutrient- and energy -deprivation-induced cell death. Biochem J. 473(6), 43-55 (2016).

4. Xing, Y., Tang, Y., Zhao, L., et al. Associations between plasma ceramides and cognitive and neuropsychiatric manifestations in Parkinson’s disease dementia. J. Neurol. Sci. 370, 82-87 (2016).

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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

String Representations

InChiKey (Click to copy)

ZKRPGPZHULJLKJ-JHRQRACZSA-N

InChi (Click to copy)

InChI=1S/C32H63NO3/c1-3-5-7-9-11-13-15-16-18-19-21-23-25-27-31(35)30(29-34)33-32(36)28-26-24-22-20-17-14-12-10-8-6-4-2/h25,27,30-31,34-35H,3-24,26,28-29H2,1-2H3,(H,33,36)/b27-25+/t30-,31+/m0/s1

SMILES (Click to copy)

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