LIPID MAPS

Structure Database (LMSD)

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Common Name

Cer(d18:1/22:0)

Systematic Name

N-(docosanoyl)-sphing-4-enine

Synonyms

C22 Cer
N-(docosanoyl)-ceramide
N-(docosanoyl)-ceramide
N-behenoyl-sphingosine
Cer[NS]

LM ID

LMSP02010008

Formula

C₄₀H₇₉NO₃

Exact Mass

Calculate m/z

621.605994

Sum Composition

Cer 40:1;O2

Abbrev Chains

Cer 18:1;O2/22:0

Status

Curated

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Classification

Biological Context

C22 ceramide is an endogenous bioactive sphingolipid. Ceramides are involved in permeabilization of the mitochondrial outer membrane during apoptosis via the intrinsic pathway.¹ C22 ceramide forms small channels in liposomes, whereas C16 ceramide forms channels that can grow in size, suggesting that acyl chain length of ceramides is important in mitochondrial-mediated apoptosis. In addition, the mitochondrial-to-cytosolic stress response (MCSR) in C. elegans fed C22 ceramide decreases following inhibition of Hsp6 (mortalin/Grp75/mtHsp70) using RNAi.²

This information has been provided by Cayman Chemical

References

1. Kim, H.E., Grant, A.R., Simic, M.S., et al. Lipid biosynthesis coordinates a mitochondrial-to-cytosolic stress response. Cell 166(6), 1539-1552 (2016).

2. Stiban, J., and Perera, M. Very long chain ceramides interfere with C16-ceramide-induced channel formation: A plausible mechanism for regulating the initiation of intrinsic apoptosis. Biochim. Biophys. Acta 1848(2), 561-567 (2015).

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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)

KEPQASGDXIEOIL-GLQCRSEXSA-N

InChi (Click to copy)

InChI=1S/C40H79NO3/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-26-28-30-32-34-36-40(44)41-38(37-42)39(43)35-33-31-29-27-25-23-16-14-12-10-8-6-4-2/h33,35,38-39,42-43H,3-32,34,36-37H2,1-2H3,(H,41,44)/b35-33+/t38-,39+/m0/s1

SMILES (Click to copy)

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