LIPID MAPS

Structure Database (LMSD)

Download as... MDLMOL SDF CSV TSV PNG SVG

Common Name

Cer(m18:0/22:0)

Systematic Name

N-(docosanoyl)-1-deoxysphinganine

Synonyms

C22DH 1-deoxyCer

LM ID

LMSP00000016

Formula

C₄₀H₈₁NO₂

Exact Mass

Calculate m/z

607.62673

Sum Composition

Cer 40:0;O

Abbrev Chains

Cer 18:0;O/22:0

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

C22 dihydro 1-Deoxyceramide (m18:0/22:0) 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 C22 dihydro 1-Deoxyceramide (m18:0/22:0) has been found in mouse embryonic fibroblasts (MEFs) following application of 1-deoxysphinganine alkyne or 1-deoxysphinganine-d3.3 It has also been found as the most prevalent dihydro deoxyceramide species in mouse brain, spinal cord, and sciatic nerve at one, three, and six months of age.⁴

This information has been provided by Cayman Chemical

References

1. Schwartz, N.U., Mileva, I., Gurevich, M., et al. Quantifying 1-deoxydihydroceramides and 1-deoxyceramides in mouse nervous system tissue. Prostaglandins Other Lipid Mediat. 141, 40-48 (2019).

2. 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).

3. 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).

4. 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).

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)

Elucidating the chemical structure of native 1-deoxysphingosine.,
J Lipid Res, 2016

Pubmed ID: 27165858

DOI: 10.1194/jlr.M067033

String Representations

InChiKey (Click to copy)

ILZRBDCCCUQGLC-ZESVVUHVSA-N

InChi (Click to copy)

InChI=1S/C40H81NO2/c1-4-6-8-10-12-14-16-18-19-20-21-22-23-25-27-29-31-33-35-37-40(43)41-38(3)39(42)36-34-32-30-28-26-24-17-15-13-11-9-7-5-2/h38-39,42H,4-37H2,1-3H3,(H,41,43)/t38-,39+/m0/s1

SMILES (Click to copy)

[C@](C)([H])(NC(CCCCCCCCCCCCCCCCCCCCC)=O)[C@]([H])(O)CCCCCCCCCCCCCCC