Cer 18:0;3/16:0;0 (YMDB01102)

Identification
YMDB IDYMDB01102
NameCer 18:0;3/16:0;0
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description

Cer 18:0;3/16:0;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]

Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • N-(Hexadecanoyl)-4S-hydroxysphinganine
  • N-(Hexadecanoyl)-phytoceramide
  • N-(Palmitoyl)-phytoceramide
  • N-Hexadecanoyl-4-hydroxysphinganine
  • Cer(t18:0/16:0)
  • N-(Hexadecanoyl)-4R-hydroxysphinganine
CAS numberNot Available
WeightAverage: 555.916
Monoisotopic: 555.522659701
InChI KeyIVBULNXGVIHEKN-MVIDNBQJSA-N
InChIInChI=1S/C34H69NO4/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-33(38)35-31(30-36)34(39)32(37)28-26-24-22-20-18-16-14-12-10-8-6-4-2/h31-32,34,36-37,39H,3-30H2,1-2H3,(H,35,38)/t31-,32+,34-/m0/s1
IUPAC NameN-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]hexadecanamide
Traditional IUPAC NameN-(palmitoyl)-phytoceramide
Chemical FormulaC34H69NO4
SMILES[H][C@@](O)([C@H](O)CCCCCCCCCCCCCC)[C@]([H])(CO)NC(=O)CCCCCCCCCCCCCCC
Chemical Taxonomy
Description 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
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Polyol
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Organic nitrogen compound
  • Carbonyl group
  • Primary alcohol
  • Hydrocarbon derivative
  • 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 Solubility0.00013 g/LALOGPS
logP8.76ALOGPS
logP10ChemAxon
logS-6.6ALOGPS
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 Count31ChemAxon
Refractivity166.17 m³·mol⁻¹ChemAxon
Polarizability73.89 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 PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05n0-0025090000-fbaa290f8d7609218d60JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08gj-6192010000-6b251d870dbc2b4e41cbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-6792000000-1a28fbbbb9a61abc648eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-0052090000-bfe226fb5d99bd01ed83JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kaa-1091010000-73a742135fc960b6db47JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9170000000-7187875d2a3672092ee2JSpectraViewer
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 ID65107
HMDB IDNot Available
Pubchem Compound ID10506988
Kegg IDNot Available
ChemSpider ID24765759
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available