N-(15Z-tetracosenoyl)-sphinganine
Basic information
- CAS
352518-80-0- Standard SMILES
CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)CCCCCCCCCCCCCCC- InChIKey
YUULKFVZRXQHPM-ATHUGRIKSA-N- Molecular formula
- C42H83NO3
- Average molar mass
- 650.1 g/mol
- Monoisotopic mass
- 649.63729551
Overview
N-[(15Z)-tetracosenoyl]sphinganine is a dihydroceramide in which the ceramide N-acyl group is specified as (15Z)-tetracosenoyl (nervonoyl). It has a role as a mouse metabolite. It is a C24:1-sphinganine and a Cer(d42:1). It is functionally related to a (15Z)-tetracosenoic acid.
Names & identifiers
- Preferred name
- N-(15Z-tetracosenoyl)-sphinganine
- IUPAC
- (Z)-N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]tetracos-15-enamide
- English name
- N-nervonoyl-D-erythro-sphinganine
- Molecular formula
- C42H83NO3
- Molecular weight
- 650.11
Names & synonyms
N-(15Z-tetracosenoyl)-sphinganine352518-80-0N-nervonoyl-D-erythro-sphinganineC24:1 Dihydroceramide (d18:0/24:1(15Z))C24:1-dihydro-CeramideCer(d18:0/24:1(15Z))C24:1DH CerN-[(15Z)-tetracosenoyl]sphinganineN-(15Z-tetracosenoyl)-dihydroceramide(15Z)-N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]tetracos-15-enamideC24:1 SphinganineN-24:1 Sphinganine
Show more names
15-Tetracosenamide, N-[(1S,2R)-2-hydroxy-1-(hydroxymethyl)heptadecyl]-, (15Z)-
C24:1 dihydrosphingosine(Z)-N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]tetracos-15-enamideLMSP02020011N-nervonoylsphinganineN-nervonyl-sphinganineN-nervonoyldihydrosphingosineN-15Z-C24:1 sphinganineSCHEMBL29472490
Database identifiers
- CAS
352518-80-0- PubChem CID
- 5283576
- DTXSID
DTXSID60415277- ChEBI
CHEBI:74130
Properties
Computed structural properties
- XLogP
- 16.8
- Topological polar surface area
- 69.6 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 38
- Heavy atoms
- 46
- Formal charge
- 0
- Complexity
- 622
Experimental & physicochemical properties
LipidsLipids -> Sphingolipids [SP] -> Ceramides [SP02] -> N-acylsphinganines (dihydroceramides) [SP0202]
Physical DescriptionSolid
Physicochemical properties
- Boiling point
- 750 · 750.0±50.0 °C(Predicted)
- Density
- 0.906 · 0.906±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- pka
- 14.3 · 14.30±0.20(Predicted)
- form
- powder
- InChIKey
- YUULKFVZRXQHPM-ATHUGRIKSA-N
- SMILES
- OC[C@]([H])(NC(CCCCCCCCCCCCC/C=C\CCCCCCCC)=O)[C@]([H])(O)CCCCCCCCCCCCCCC
- UNSPSC Code
- 12352211 · 12352211
- NACRES
- 25 · NA.25
- WGK Germany
- 3 · WGK 3
- Storage Class
- 11 · 11 - Combustible Solids
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
- wgk
- WGK 3
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Applications
UsesC24:1 Dihydroceramide has been used as a standard in quadrupole time-of-flight (Q-TOF) mass spectrometry for the measurement of sphingolipid metabolites in adipose tissue. It has also been used a standard in diacylglycerol kinase (DGK) assay to quantify dihydroceramides in CLN9-deficient cells.
Additional notes
DefinitionChEBI: N-[(15Z)-tetracosenoyl]sphinganine is a dihydroceramide in which the ceramide N-acyl group is specified as (15Z)-tetracosenoyl (nervonoyl). It has a role as a mouse metabolite. It is a C24:1-sphinganine and a Cer(d42:1). It is functionally related to a (15Z)-tetracosenoic acid.
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