C16-Ceramide
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Basic information
- CAS
24696-26-2- Standard SMILES
CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO)NC(=O)CCCCCCCCCCCCCCC- InChIKey
YDNKGFDKKRUKPY-TURZORIXSA-N- Molecular formula
- C34H67NO3
- Average molar mass
- 537.9 g/mol
- Monoisotopic mass
- 537.512095
Overview
N-hexadecanoylsphingosine is a N-acylsphingosine in which the ceramide N-acyl group is specified as hexadecanoyl (palmitoyl). It has a role as a Mycoplasma genitalium metabolite and a human blood serum metabolite. It is a Cer(d34:1), a N-palmitoyl-sphingoid base and a N-acylsphingosine. It is functionally related to a hexadecanoic acid.
Names & identifiers
- Preferred name
- C16-Ceramide
- IUPAC
- N-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]hexadecanamide
- English name
- C16 CERAMIDE
- Molecular formula
- C34H67NO3
- Molecular weight
- 537.9
Names & synonyms
C16-ceramideC16 CeramideDTXSID301317974RefChem:573083DTXCID501747767640-541-524696-26-2N-palmitoyl-D-erythro-sphingosineN-(hexadecanoyl)-sphing-4-enineCer(d18:1/16:0)N-palmitoyl-sphingosineN-acylsphingosine
Show more names
N-PALMITOYL-D-SPHINGOSINEN-Palmitoylsphingosine16:0 CERAMIDEC16 Ceramide (d18:1/16:0)CERAMIDE-C16PALMITOYL CERAMIDEN-PALMITOYL CERAMIDE
N-hexadecanoylsphingosineN-hexadecanoyl-D-erythro-sphingosineC16 CerCeramide (Egg, Chicken)N-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]hexadecanamideCHEMBL35292N-((2S,3R,E)-1,3-dihydroxyoctadec-4-en-2-yl)palmitamideCHEBI:72959
Database identifiers
- CAS
24696-26-2- PubChem CID
- 5283564
- DTXSID
DTXSID301317974- ChEMBL
CHEMBL35292- ChEBI
CHEBI:72959- UNII
- FD38GFZ87C
- EC Number
- 640-541-5
- Nikkaji
- J2.856.006K、J525.581C
Properties
Computed structural propertiesFilling in
- XLogP
- 12.9
- Topological polar surface area
- 69.6 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 30
- Heavy atoms
- 38
- Formal charge
- 0
- Complexity
- 508
Experimental & physicochemical properties
Lipids
Lipids -> Sphingolipids
Lipids -> Sphingolipids [SP] -> Ceramides [SP02] -> N-acylsphingosines (ceramides) [SP0201]
SolubilityInsoluble
Physical DescriptionSolid
Collision Cross Section251.1 Ų [M+HCOO]- [CCS Type: DT; Buffer gas: N2; Sample Type: Human bronchoalveolar lavage fluid (BALF); Dataset: Sphingolipids]
Physicochemical properties
- Melting point
- 94 · 94-95 °C
- Boiling point
- 614.41 °C · 614.41°C (rough estimate)
- Density
- 0.9596 · 0.9596 (rough estimate)
- refractive index
- 1.663 · 1.6630 (estimate)
- storage temp.
- 20 °C · −20°C
- solubility
- 0.15 mg/ml · Soluble in DMF at 0.15mg/ml
- pka
- 13.54 · 13.54±0.20(Predicted)
- form
- Crystalline Powder
- color
- White
- InChIKey
- YDNKGFDKKRUKPY-TURZORIXSA-N
- SMILES
- C(N[C@@H](CO)[C@H](O)/C=C/CCCCCCCCCCCCC)(=O)CCCCCCCCCCCCCCC
- CAS DataBase Reference
- 24696 · 24696-26-2
- UNSPSC Code
- 12352211 · 12352211
- NACRES
- 85 · NA.85
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P280a-P304+P340-P305+P351+P338-P405-P501a
- Hazard Codes
- Xi
- Safety Statements
- 24 · 24/25
- WGK Germany
- 3 · 3
- HS Code
- 29225000 · 29225000
- 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.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- wgk
- 3
- hs_code
- 29225000
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Chemistry & industry
Pharmacology
Tissue LocationsBrain
Cellular LocationsExtracellular
Applications
UsesA predominant, rather hydrophobic natural ceramide. Activates a cytosolic serine/threonine protein phosphatase in T9 cells; induces EGF receptor phosphorylation in A-431 cells; stimulates ceramide-activated protein kinase
UsesAn endogenous ceramide that acts as a lipid second messenger to regulate apoptosis and stress signaling.
Additional notes
DefinitionChEBI: N-hexadecanoylsphingosine is a N-acylsphingosine in which the ceramide N-acyl group is specified as hexadecanoyl (palmitoyl). It has a role as a Mycoplasma genitalium metabolite and a human blood serum metabolite. It is a N-acylsphingosine, a Cer(d34:1) and a N-palmitoyl-sphingoid base. It is functionally related to a hexadecanoic acid.
Related reactions
1 records
Compound notes
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