LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG

Common Name

Cer(d18:0/24:0)

Systematic Name

N-(tetracosanoyl)-sphinganine

Synonyms

C24DH Cer
N-(tetracosanoyl)-dihydroceramide
N-(tetracosanoyl)-dihydroceramide
Cer[NdS]

LM ID

LMSP02020012

Formula

C₄₂H₈₅NO₃

Exact Mass

Calculate m/z

651.652944

Sum Composition

Cer 42:0;O2

Abbrev Chains

Cer 18:0;O2/24:0

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

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

Classification

Biological Context

C24 dihydro Ceramide is a sphingolipid that has been found in the stratum corneum of human skin.¹ It is found in higher concentrations in female sebum compared to male sebum.² C24 dihydro Ceramide levels positively correlate with cytotoxicity in CCRF-CEM, MOLT-4, COG-LL-317h, and COG-LL-332h T cell acute lymphoblastic leukemia (ALL) cell lines.³ Levels of C24 dihydro ceramide are increased by 149.49-fold in dihydroceramide desaturase 1 (DEGS1) knockdown UM-SCC-22A human head and neck squamous carcinoma cells in vitro. 4 C24 dihydro Ceramide levels are also increased in INS-1 β-cells incubated with glucose and palmitate .⁵

This information has been provided by Cayman Chemical

References

1. Farwanah, H., Wohlrab, J., Neubert, R.H., et al. Profiling of human stratum corneum ceramides by means of normal phase LC/APCI-MS. Anal. Bioanal. Chem. 383(4), 632-637 (2005).

2. Agrawal, K., Hassoun, L.A., Foolad, N., et al. Effects of atopic dermatitis and gender on sebum lipid mediator and fatty acid profiles. Prostaglandins Leukot. Essent. Fatty Acids 134, 7-16 (2018).

3. Holliday, M.W., Jr., Cox, S.B., Kang, M.H., et al. C22:0- and C24:0-dihydroceramides confer mixed cytotoxicity in T-cell acute lymphoblastic leukemia cell lines. PLoS One 8(9), (2013).

4. Breen, P., Jospeh, N., Thompson, K., et al. Dihydroceramide desaturase knockdown impacts sphingolipids and apoptosis after photodamage in human head and neck squamous carcinoma cells. Anticancer Res. 33(1), 77-84 (2013).

5. Véret, J., Coant, N., Berdyshev, E.V., et al. Ceramide synthase 4 and de novo production of ceramides with specific N-acyl chain lengths are involved in gluco-lipotoxicity-induced apoptosis of INS-1 β-cells. Biochem J. 438(1), 177-189 (2011).

Reactions

Filter by species:

Click on an edge to display the reaction(s).

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)

BPLYVSYSBPLDOA-WVILEFPPSA-N

InChi (Click to copy)

InChI=1S/C42H85NO3/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-42(46)43-40(39-44)41(45)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2/h40-41,44-45H,3-39H2,1-2H3,(H,43,46)/t40-,41+/m0/s1

SMILES (Click to copy)

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