Cer(d18:1/22:0)
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Basic information
- CAS
27888-44-4- Standard SMILES
CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO)NC(=O)CCCCCCCCCCCCCCCCCCCCC- InChIKey
KEPQASGDXIEOIL-GLQCRSEXSA-N- Molecular formula
- C40H79NO3
- Average molar mass
- 622.1 g/mol
- Monoisotopic mass
- 621.60599538
Overview
N-docosanoylsphingosine is a N-acylsphingosine in which the ceramide N-acyl group is specified as docosanoyl. It has a role as a mouse metabolite. It is a Cer(d40:1) and a N-acylsphingosine. It is functionally related to a docosanoic acid.
Names & identifiers
- Preferred name
- Cer(d18:1/22:0)
- IUPAC
- N-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]docosanamide
- English name
- N-behenoyl-D-erythro-sphingosine
- Molecular formula
- C40H79NO3
- Molecular weight
- 622.06
Names & synonyms
Cer(d18:1/22:0)N-(docosanoyl)-sphing-4-enineC22 CerRefChem:1081344C22 Ceramide27888-44-4N-docosanoylsphingosine869501-30-4C22-CeramideC22 Ceramide (d18:1/22:0)N-Behenoyl-D-erythro-sphingosineN-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]docosanamide
Show more names
C22 Ceramide (d18:1/22:0) (Standard)C22 Ceramide-Stable isotope(d18:1-d7/22:0)Cer(d18:1/22:0)/N-(docosanoyl)-sphing-4-enineCer(d18:1/22:0)|||C22 Ceramide|||Ceramide (d18:1/22:0)Docosanamide, N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-
N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]docosanamideN-((2S,3R,E)-1,3-Dihydroxyoctadec-4-en-2-yl)docosanamideN-behenoylsphingosineCeramide d40:1LMSP02010008N-behenoyl-sphingosineN-(docosanoyl)ceramideN-(docosanoyl)-ceramide
Database identifiers
Properties
Computed structural propertiesFilling in
- XLogP
- 16.1
- Topological polar surface area
- 69.6 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 36
- Heavy atoms
- 44
- Formal charge
- 0
- Complexity
- 593
Experimental & physicochemical properties
LipidsLipids -> Sphingolipids [SP] -> Ceramides [SP02] -> N-acylsphingosines (ceramides) [SP0201]
SolubilityInsoluble
Physical DescriptionSolid
Physicochemical properties
- Boiling point
- 731.8 · 731.8±60.0 °C(Predicted)
- Density
- 0.909 · 0.909±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- 0.15 mg/ml · DMF: 0.15 mg/ml
- form
- A crystalline solid
- pka
- 13.54 · 13.54±0.20(Predicted)
- color
- White to off-white
- InChIKey
- KEPQASGDXIEOIL-GLQCRSEXSA-N
- SMILES
- C(N[C@@H](CO)[C@H](O)/C=C/CCCCCCCCCCCCC)(=O)CCCCCCCCCCCCCCCCCCCCC
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
Tissue LocationsBrain
Cellular LocationsExtracellular
Applications
UsesC22 Ceramide (d18:1/22:0) has been used:as a standard to measure ceramide concentrations in muscle tissue samples using high-performance liquid chromatography/tandem mass spectrometry (LC/MS2)as a standard for the quantitation of sphingolipid metabolitesto study its effects on mitochondrial-to-cytosolic stress response (MCSR) induction
Additional notes
DefinitionChEBI: N-docosanoylsphingosine is a N-acylsphingosine in which the ceramide N-acyl group is specified as docosanoyl. It has a role as a mouse metabolite. It is a N-acylsphingosine and a Cer(d40:1). It is functionally related to a docosanoic acid.
Related reactions
0 records
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Compound notes
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