N-(oleoyl)-ceramide
Basic information
- CAS
5966-28-9- Standard SMILES
CCCCCCCC/C=C\CCCCCCCC(=O)N[C@@H](CO)[C@H](O)/C=C/CCCCCCCCCCCCC- InChIKey
OBFSLMQLPNKVRW-RHPAUOISSA-N- Molecular formula
- C36H69NO3
- Average molar mass
- 563.9 g/mol
- Monoisotopic mass
- 563.52774506
Overview
N-oleoylsphingosine is a N-acylsphingosine in which the ceramide N-acyl group is specified as oleoyl. It has a role as a mouse metabolite. It is functionally related to an oleic acid.
Names & identifiers
- Preferred name
- N-(oleoyl)-ceramide
- IUPAC
- (Z)-N-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]octadec-9-enamide
- English name
- N-OLEOYL-D-SPHINGOSINE
- Molecular formula
- C36H69NO3
- Molecular weight
- 563.94
Names & synonyms
N-(oleoyl)-ceramide(Z)-N-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]octadec-9-enamideDTXSID00415271(Z)-N-((E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl)octadec-9-enamideRefChem:1091447DTXCID903661225966-28-9C18:1-Ceramiden-oleoylsphingosineN-OLEOYL-D-SPHINGOSINEN-oleoyl-D-erythro-sphingosineN-(9Z-octadecenoyl)-sphing-4-enine
Show more names
18:1 CERAMIDEC18:1 CERAMIDEOLEOYL CERAMIDEN-CIS-OCTADECENOYL-D-SPHINGOSINED-ERYTHRO-SPHINGOSINE, N-OLEOYL-n-oleoyl-d-sphingosine semisyntheticN-(cis-9-Octadecenoyl)-D-sphingosine
Cer(d18:1/18:1(9Z))C18:1 Ceramide (d18:1/18:1(9Z))C18:1 Cer(9Z)-N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]octadec-9-enamideN-(9Z-octadecenoyl)-ceramiden-oleoyl sphingosineN-oleoyl-sphingosineLMSP02010003
Database identifiers
- CAS
Properties
Computed structural properties
- XLogP
- 13
- Topological polar surface area
- 69.6 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 31
- Heavy atoms
- 40
- Formal charge
- 0
- Complexity
- 574
Experimental & physicochemical properties
LipidsLipids -> Sphingolipids [SP] -> Ceramides [SP02] -> N-acylsphingosines (ceramides) [SP0201]
SolubilityInsoluble
Physical DescriptionSolid
Physicochemical properties
- Boiling point
- 694.255 · 694.255±55.00 °C(Press: 760.00 Torr)(predicted)
- Density
- 0.922 · 0.922±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
- storage temp.
- 20 °C · −20°C
- solubility
- 0.15 mg/ml · Chloroform: Soluble; DMF: 0.15 mg/ml
- pka
- 13.541 · 13.541±0.20(predicted)
- form
- lyophilized powder
- color
- White to off-white
- BRN
- 6283861 · 6283861
- InChIKey
- OBFSLMQLPNKVRW-RHPAUOISSA-N
- SMILES
- OC[C@]([H])(NC(CCCCCCC/C=C\CCCCCCCC)=O)[C@]([H])(O)/C=C/CCCCCCCCCCCCC
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
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
Tissue LocationsBrain
Cellular LocationsExtracellular
Applications
DescriptionC18:1 Ceramide is a naturally occurring ceramide. Levels of C18:1 ceramide are elevated in overweight and insulin-resistant mice and cattle. C18:1 Ceramide is also increased in the plasma and ovarian tissue of patients with advanced ovarian cancer.
UsesN-Oleoyl-D-erythro-sphingosine is a member of the ceramide family.
Additional notes
DefinitionChEBI: N-oleoylsphingosine is a N-acylsphingosine in which the ceramide N-acyl group is specified as oleoyl. It has a role as a mouse metabolite. It is functionally related to an oleic acid.
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