N-(docosanoyl)-sphinganine
Basic information
- CAS
147492-65-7- Standard SMILES
CCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)CCCCCCCCCCCCCCC- InChIKey
SXPRAKSDHOEHIG-ZESVVUHVSA-N- Molecular formula
- C40H81NO3
- Average molar mass
- 624.1 g/mol
- Monoisotopic mass
- 623.62164545
Overview
N-docosanoylsphinganine is a dihydroceramide in which the ceramide N-acyl group is specified as docosanoyl (behenoyl). It has a role as a mouse metabolite. It is functionally related to a docosanoic acid.
Names & identifiers
- Preferred name
- N-(docosanoyl)-sphinganine
- IUPAC
- N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]docosanamide
- English name
- C22 Dihydroceramide
- Molecular formula
- C40H81NO3
- Molecular weight
- 624.08
Names & synonyms
N-(docosanoyl)-sphinganineN-docosanoylsphinganineC22DH CerN-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]docosanamideN-(docosanoyl)-dihydroceramideCHEBI:67021N-((2S,3R)-1,3-Dihydroxyoctadecan-2-yl)docosanamideRefChem:1091424C22 Dihydroceramide147492-65-7Cer(d18:0/22:0)Cer(40:0)
Show more names
N-[(1S,2R)-2-Hydroxy-1-(hydroxymethyl)-heptadecyl]-docosanamide
Docosanamide, N-[(1S,2R)-2-hydroxy-1-(hydroxymethyl)heptadecyl]-C22 sphinganineN-behenoylsphinganineC22-DihydroceramideCeramide d40:0LMSP02020010N-behenoyldihydroceramideN-docosanoyldihydroceramide
Database identifiers
- CAS
147492-65-7- PubChem CID
- 5283575
- DTXSID
DTXSID00415276- ChEBI
CHEBI:67021- Nikkaji
- J1.195.803F
Properties
Computed structural properties
- XLogP
- 16.6
- Topological polar surface area
- 69.6 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 37
- Heavy atoms
- 44
- Formal charge
- 0
- Complexity
- 555
Experimental & physicochemical properties
Lipids
Lipids -> Sphingolipids
Lipids -> Sphingolipids [SP] -> Ceramides [SP02] -> N-acylsphinganines (dihydroceramides) [SP0202]
Physical DescriptionSolid
Collision Cross Section
275.9 Ų [M+CH3COO]- [CCS Type: DT; Buffer gas: N2; Sample Type: Human plasma; Dataset: Sphingolipids]
274.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with phosphatidylcholines (ESI+) and phosphatidylethanolamines (ESI-)]
274.03 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]
274.7 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
Physicochemical properties
- Melting point
- 97 · 97-99°C
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- Chloroform (Slightly, Heated), Methanol (Slightly, Heated)
- form
- Solid
- color
- White
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Applications
UsesC22 Dihydroceramide (cas# 147492-65-7) is a compound useful in organic synthesis.
Additional notes
DefinitionChEBI: N-docosanoylsphinganine is a dihydroceramide in which the ceramide N-acyl group is specified as docosanoyl (behenoyl). It has a role as a mouse metabolite. It is functionally related to a docosanoic acid.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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