C18-Ceramide
Basic information
- CAS
2304-81-6- Standard SMILES
CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO)NC(=O)CCCCCCCCCCCCCCCCC- InChIKey
VODZWWMEJITOND-NXCSZAMKSA-N- Molecular formula
- C36H71NO3
- Average molar mass
- 566 g/mol
- Monoisotopic mass
- 565.54339513
Overview
N-octadecanoylsphingosine is a N-acylsphingosine in which the ceramide N-acyl group is specified as octadecanoyl (stearoyl). It has a role as a mouse metabolite. It is a N-stearoyl-sphingoid base and a N-acylsphingosine. It is functionally related to an octadecanoic acid.
Names & identifiers
- Preferred name
- C18-Ceramide
- IUPAC
- N-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]octadecanamide
- English name
- C18 CERAMIDE
- Molecular formula
- C36H71NO3
- Molecular weight
- 565.96
Names & synonyms
2304-81-6C18-CERAMIDEN-stearoyl-D-erythro-sphingosineV3Q7C63KSSDTXSID001317818RefChem:1080585DTXCID4068955C18 CeramideN-StearoylsphingosineN-Stearoyl-D-sphingosineCer(d18:1/18:0)C18 Ceramide (d18:1/18:0)
Show more names
N-STEAROYLSPHINGANINECERAMIDE NS18:0 CERAMIDEceramide c18Ceramide C18 D5C18 Ceramide NSSTEAROYL CERAMIDEN-18:0 SPHINGANINEN-STEAROYL CERAMIDE
N-octadecanoylsphingosineN-(octadecanoyl)-sphing-4-enineN-((2S,3R,E)-1,3-dihydroxyoctadec-4-en-2-yl)stearamideC18 CerN-(octadecanoyl)ceramideN-(octadecanoyl)-ceramideCeramide (d18:1/18:0)CHEBI:72961
Database identifiers
- CAS
2304-81-6- PubChem CID
- 5283565
- DTXSID
DTXSID001317818- ChEBI
CHEBI:72961
Properties
Computed structural properties
- XLogP
- 13.9
- Topological polar surface area
- 69.6 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 32
- Heavy atoms
- 40
- Formal charge
- 0
- Complexity
- 536
Experimental & physicochemical properties
Lipids
Lipids -> Sphingolipids
Lipids -> Sphingolipids [SP] -> Ceramides [SP02] -> N-acylsphingosines (ceramides) [SP0201]
SolubilityInsoluble
Physical DescriptionSolid
Collision Cross Section
257.6 Ų [M+HCOO]- [CCS Type: DT; Buffer gas: N2; Sample Type: Human bronchoalveolar lavage fluid (BALF); Dataset: Sphingolipids]
248.67 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
Physicochemical properties
- Melting point
- 99 · 99-101 °C
- Boiling point
- 630.97 °C · 630.97°C (rough estimate)
- alpha
- 20 · [α]D20 -2~-5゜ (c=0.5, CHCl3)
- Density
- 0.9512 · 0.9512 (rough estimate)
- refractive index
- 1.663 · 1.6630 (estimate)
- storage temp.
- 20 °C · −20°C
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
- 3
- hs_code
- 29225000
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
Tissue LocationsBrain
Cellular LocationsExtracellular
Metabolite PathwaysFabry disease
Applications
UsesThe sphingolipid ceramide is a potent inhibitor of the mitochondrial permeability transition pore.
Additional notes
DefinitionChEBI: N-octadecanoylsphingosine is a N-acylsphingosine in which the ceramide N-acyl group is specified as octadecanoyl (stearoyl). It has a role as a mouse metabolite. It is a N-acylsphingosine and a N-stearoyl-sphingoid base. It is functionally related to an octadecanoic acid.
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