LIPID MAPS

Structure Database (LMSD)

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Common Name

Cer(m18:0/24:1(15Z))

Systematic Name

N-(15Z-tetracosenoyl)-1-deoxysphinganine

Synonyms

C24:1DH 1-deoxyCer

LM ID

LMSP00000013

Formula

C₄₂H₈₃NO₂

Exact Mass

Calculate m/z

633.642379

Sum Composition

Cer 42:1;O

Abbrev Chains

Cer 18:0;O/24:1

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

C24:1 dihydro 1-Deoxyceramide (m18:0/24:1) is a very long-chain atypical ceramide containing a 1-deoxysphinganine (m18:0) backbone. 1-Deoxysphingolipids are formed when serine palmitoyltransferase condenses palmitoyl-CoA with alanine instead of serine during sphingolipid synthesis.^1,2 C24:1 dihydro 1-Deoxyceramide (m18:0/24:1) has been found as a major 1-deoxyceramide species in mouse embryonic fibroblasts (MEFs) following application of 1-deoxysphinganine alkyne or 1-deoxysphinanine-d3.3

This information has been provided by Cayman Chemical

References

1. Steiner, R., Saied, E.M., Othman, A., et al. Elucidating the chemical structure of native 1-deoxysphingosine. J. Lipid Res. 57(7), 1194-1203 (2016).

2. Alecu, I., Tedeschi, A., Behler, N., et al. Localization of 1-deoxysphingolipids to mitochondria induces mitochondrial dysfunction. J. Lipid. Res. 58(1), 42-59 (2017).

3. Alecu, I., Othman, A., Penno, A., et al. Cytotoxic 1-deoxysphingolipids are metabolized by a cytochrome P450-dependent pathway. J. Lipid Res. 58(1), 60-71 (2017).

String Representations

InChiKey (Click to copy)

XBNZFPFCTSJHRI-FIIAPBGQSA-N

InChi (Click to copy)

InChI=1S/C42H83NO2/c1-4-6-8-10-12-14-16-18-19-20-21-22-23-24-25-27-29-31-33-35-37-39-42(45)43-40(3)41(44)38-36-34-32-30-28-26-17-15-13-11-9-7-5-2/h18-19,40-41,44H,4-17,20-39H2,1-3H3,(H,43,45)/b19-18-/t40-,41+/m0/s1

SMILES (Click to copy)

[C@](C)([H])(NC(CCCCCCCCCCCCC/C=C\CCCCCCCC)=O)[C@]([H])(O)CCCCCCCCCCCCCCC