[3-Acetyloxy-2-(hexacosanoylamino)-1-hydroxyoctadecan-4-yl] acetate
Basic information
- CAS
104404-17-3- Standard SMILES
CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)NC(CO)C(OC(C)=O)C(CCCCCCCCCCCCCC)OC(C)=O- InChIKey
XJRPTDNTEPSGLZ-UHFFFAOYSA-N- Molecular formula
- C48H93NO6
- Average molar mass
- 780.3 g/mol
Names & identifiers
- Preferred name
- [3-Acetyloxy-2-(hexacosanoylamino)-1-hydroxyoctadecan-4-yl] acetate
- IUPAC
- [3-acetyloxy-2-(hexacosanoylamino)-1-hydroxyoctadecan-4-yl] acetate
- English name
- Ceramide
- Molecular formula
- C34H66NO3R
- Molecular weight
- 536.89
Names & synonyms
Ceramide (d18:1/9Z-18:1)Ceramide (d18:1/26:1(17Z))CERAMIDEN-oleoylsphingosineCeramide (d18:1/16:0)Ceramide (d18:1/12:0)Ceramide (d18:1/18:0)Ceramide (d18:1/20:0)Ceramide (d18:1/22:0)Ceramide (d18:1/24:0)
Database identifiers
- CAS
104404-17-3
Properties
Computed structural properties
- XLogP
- 18.8
- Topological polar surface area
- 102 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 45
- Heavy atoms
- 55
- Formal charge
- 0
- Complexity
- 850
Physicochemical properties
- InChIKey
- XJRPTDNTEPSGLZ-UHFFFAOYSA-N
- SMILES
- C(OC(C)=O)(C(CCCCCCCCCCCCCC)OC(C)=O)C(CO)NC(CCCCCCCCCCCCCCCCCCCCCCCCC)=O
Chemistry & industry
Applications
UsesCeramides are a class of complex sphingolipids that act as second messengers in processes such as cell growth, differentiation, stress response, inflammatory signal transduction, and apoptosis. They are associated with the pathogenesis of various diseases and can serve as biomarkers for disease detection and prognosis, playing a significant role in diseases such as coronary heart disease, myocardial infarction, and coronary atherosclerosis in cardiovascular diseases (CVD). Furthermore, they possess moisturizing and skin-repairing properties and are widely used in skin care and cosmetic formulations.
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.
Related reactions
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Compound notes
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