Cer(d18:1/14:0) (CHEM040470)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 20:39:38 UTC
Update Date2016-11-09 01:22:15 UTC
Accession NumberCHEM040470
Identification
Common NameCer(d18:1/14:0)
ClassSmall Molecule
DescriptionCeramides (N-acylsphingosine) are one of the hydrolysis byproducts of sphingomyelin by the enzyme sphingomyelinase (sphingomyelin phosphorylcholine phosphohydrolase E.C.3.1.4.12) which has been identified in the subcellular fractions of human epidermis (PMID 25935) and many other tissues. They can also be synthesized from serine and palmitate in a de novo pathway and are regarded as important cellular signals for inducing apoptosis (PMID 14998372). Is key in the biosynthesis of glycosphingolipids and gangliosides.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
C14 CerChEBI
N-(Myristoyl)ceramideChEBI
N-(Tetradecanoyl)ceramideChEBI
N-(Tetradecanoyl)sphing-4-enineChEBI
N-Myristoylsphing-4-enineChEBI
N-MyristoylsphingosineChEBI
N-Tetradecanoylsphing-4-enineChEBI
CeramideMetBuilder
N-(Tetradecanoyl)-sphing-4-enineMetBuilder
Ceramide(D18:1/14:0)MetBuilder
N-(Tetradecanoyl)-sphingosineMetBuilder
N-(Tetradecanoyl)-D-erythro-sphingosineMetBuilder
N-(Tetradecanoyl)-4-sphingenineMetBuilder
N-(Tetradecanoyl)-D-sphingosineMetBuilder
N-(Tetradecanoyl)-sphingenineMetBuilder
N-(Tetradecanoyl)-erythro-4-sphingenineMetBuilder
Chemical FormulaC32H63NO3
Average Molecular Mass509.848 g/mol
Monoisotopic Mass509.481 g/mol
CAS Registry NumberNot Available
IUPAC NameN-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]tetradecanamide
Traditional NameC14 cer
SMILESCCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](CO)NC(=O)CCCCCCCCCCCCC
InChI IdentifierInChI=1S/C32H63NO3/c1-3-5-7-9-11-13-15-16-18-19-21-23-25-27-31(35)30(29-34)33-32(36)28-26-24-22-20-17-14-12-10-8-6-4-2/h25,27,30-31,34-35H,3-24,26,28-29H2,1-2H3,(H,33,36)/b27-25+/t30-,31+/m0/s1
InChI KeyZKRPGPZHULJLKJ-JHRQRACZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as long-chain ceramides. These are ceramides bearing a long chain fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSphingolipids
Sub ClassCeramides
Direct ParentLong-chain ceramides
Alternative Parents
Substituents
  • Long-chain ceramide
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.8e-05 g/LALOGPS
logP9.1ALOGPS
logP9.98ChemAxon
logS-6.9ALOGPS
pKa (Strongest Acidic)13.62ChemAxon
pKa (Strongest Basic)0.02ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.56 ŲChemAxon
Rotatable Bond Count28ChemAxon
Refractivity156.57 m³·mol⁻¹ChemAxon
Polarizability68.55 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-022i-4016359000-20baf0ecf44d3da99bdaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000190000-83d83551bd85e2f61e90Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0060190000-0d216e69530b1868d9b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03ec-0090500000-7cc0e43da512bde81d35Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000090000-c391f358d8500a2694c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0010090000-92b5f813747623efeac9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a90-0090990000-b1b71e927687daed4bafSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000090000-e5bc1b9e2ad6e0903dadSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000090000-e5bc1b9e2ad6e0903dadSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0000910000-3b5c9426ac32d93af42fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000190000-76a46de188bfc8f7f75dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0060190000-e9d3327e0af8956ff47aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03ec-0090500000-14ccfa4bc4df5eb911f3Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0011773
FooDB IDFDB028443
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4445481
ChEBI ID72957
PubChem Compound ID5282310
Kegg Compound IDC13916
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Bowser PA, Gray GM: Sphingomyelinase in pig and human epidermis. J Invest Dermatol. 1978 Jun;70(6):331-5.
2. Tserng KY, Griffin RL: Ceramide metabolite, not intact ceramide molecule, may be responsible for cellular toxicity. Biochem J. 2004 Jun 15;380(Pt 3):715-22.
3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
4. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
5. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
6. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
7. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78.
8. Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50.
9. Pruett ST, Bushnev A, Hagedorn K, Adiga M, Haynes CA, Sullards MC, Liotta DC, Merrill AH Jr: Biodiversity of sphingoid bases ("sphingosines") and related amino alcohols. J Lipid Res. 2008 Aug;49(8):1621-39. doi: 10.1194/jlr.R800012-JLR200. Epub 2008 May 21.
10. Hannun YA, Obeid LM: Ceramide: an intracellular signal for apoptosis. Trends Biochem Sci. 1995 Feb;20(2):73-7.
11. Phospholipids Handbook
12. The lipid handbook with CD-ROM