Structure Database (LMSD)

Common Name
Cer(m18:0/24:0)
Systematic Name
N-(tetracosanoyl)-1-deoxysphinganine
Synonyms
  • C24DH 1-deoxyCer
LM ID
LMSP00000015
Formula
C42H85NO2
Exact Mass
Calculate m/z
635.65803
Sum Composition
Cer 42:0;O
Abbrev Chains
Cer 18:0;O/24:0
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Sphingolipids [SP]
Ceramides [SP02]
1-Deoxyceramides [SP0206]

Biological Context

24 dihydro 1-Deoxyceramide (m18:0/24:0) 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 C24 dihydro 1-Deoxyceramide (m18:0/24:0) has been found in mouse embryonic fibroblasts (MEFs) following application of 1-deoxysphinganine alkyne or 1-deoxysphinganine-d3.3 It has also been found 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).

String Representations

InChiKey (Click to copy)
PTDCLRQOABWOQP-WVILEFPPSA-N
InChi (Click to copy)
InChI=1S/C42H85NO2/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/h40-41,44H,4-39H2,1-3H3,(H,43,45)/t40-,41+/m0/s1
SMILES (Click to copy)
[C@](C)([H])(NC(CCCCCCCCCCCCCCCCCCCCCCC)=O)[C@]([H])(O)CCCCCCCCCCCCCCC

Other Databases

PubChem CID
73242206
Cayman ID
27017

Calculated Physicochemical Properties

Heavy Atoms 45
Rings 0
Aromatic Rings 0
Rotatable Bonds 38
Van der Waals Molecular Volume 761.10
Topological Polar Surface Area 49.33
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 14.51
Molar Refractivity 202.20

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Created at
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Updated at
14th Dec 2021