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Identification
YMDB IDYMDB01105
NameCer 18:0;3/22:0;0
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description

Cer 18:0;3/22:0;0 is a ceramide. Ceramides are composed of a sphingosine and a fatty acid. Ceramides are found in high concentrations within the cell membrane of cells. Caramides are known to promote transport of secretory vesicles from the ER to the Golgi apparatus. Sphingolipids like ceramide play import roles in lipid rafts which in yeast are responsible for delivering and sorting membrane bound proteins. Lipid rafts also play roles in membrane fusion during mating.[PMID: 16730802]

There are three major pathways of ceramide generation. The sphingomyelinase pathway uses an enzyme to breakdown IPC, MIPC and M(IP)2C in the cell membrane and release ceramide. The de novo pathway creates ceramide from less complex molecules. Ceramide generation can also occur through breakdown of complex sphingolipids that are ultimately broken down into sphingosine, which is then reused by reacylation to form ceramide. This latter pathway is termed the Salvage pathway.[Wikipedia, PMID: 16730802]Lipid identified in the yeast S. cerevisiae

Structure
Thumb
Synonyms
  • N-(Docosanoyl)-4-hydroxysphinganine
  • N-(Docosanoyl)-4R-hydroxysphinganine
  • N-(Docosanoyl)-phytoceramide
  • N-Behenoyl-4-hydroxysphinganine
  • N-Behenoylphytoceramide
  • N-Behenoylphytosphingosine
  • N-Docosanoylphytoceramide
  • N-Docosanoylphytosphingosine
  • PHC-b 18:0/22:0
  • Cer(t18:0/22:0)
CAS numberNot Available
WeightAverage: 640.0754
Monoisotopic: 639.616560085
InChI KeyCIMNZQFRNXDRER-HIERITDVSA-N
InChIInChI=1S/C40H81NO4/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-25-27-29-31-33-35-39(44)41-37(36-42)40(45)38(43)34-32-30-28-26-24-16-14-12-10-8-6-4-2/h37-38,40,42-43,45H,3-36H2,1-2H3,(H,41,44)/t37-,38+,40-/m0/s1
IUPAC NameN-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]docosanamide
Traditional IUPAC NameN-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]docosanamide
Chemical FormulaC40H81NO4
SMILES[H][C@@](O)([C@H](O)CCCCCCCCCCCCCC)[C@]([H])(CO)NC(=O)CCCCCCCCCCCCCCCCCCCCC
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phytoceramides. These are n-acylated 4-hydroxysphinganine.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSphingolipids
Sub ClassCeramides
Direct ParentPhytoceramides
Alternative Parents
Substituents
  • N-acyl-4-hydroxysphinganine_base
  • N-acyl-4-hydroxysphinganine
  • Fatty acyl
  • N-acyl-amine
  • Fatty amide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Polyol
  • Carboxamide group
  • 1,2-diol
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility5.7e-05 g/LALOGPS
logP9.66ALOGPS
logP12.66ChemAxon
logS-7ALOGPS
pKa (Strongest Acidic)13.26ChemAxon
pKa (Strongest Basic)0.029ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area89.79 ŲChemAxon
Rotatable Bond Count37ChemAxon
Refractivity193.78 m³·mol⁻¹ChemAxon
Polarizability87.47 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Biosynthesis of unsaturated fatty acids (docosanoyl)PW002408 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
Phytosphingosine + Docosanoyl-CoAhydron + Coenzyme A + Cer 18:0;3/22:0;0
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Ejsing, C. S., Sampaio, J. L., Surendranath, V., Duchoslav, E., Ekroos, K., Klemm, R. W., Simons, K., Shevchenko, A. (2009). "Global analysis of the yeast lipidome by quantitative shotgun mass spectrometry." Proc Natl Acad Sci U S A 106:2136-2141.19174513
  • Dickson, R. C. (2008). "Thematic review series: sphingolipids. New insights into sphingolipid metabolism and function in budding yeast." J Lipid Res 49:909-921.18296751
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID67024
HMDB IDNot Available
Pubchem Compound ID5322153
Kegg IDNot Available
ChemSpider ID4479726
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available