Cer 18:0;3/26:0;0 (YMDB01108)

Identification
YMDB IDYMDB01108
NameCer 18:0;3/26:0;0
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description

Cer 18:0;3/26:0;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
  • Cer2_26
  • Ceramide-2 (phytosphingosine:n-C26:0)
  • N-(Hexacosanoyl)-4-hydroxysphinganine
  • N-Hexacosanoyl-4-hydroxysphinganine
  • N-(Hexacosanoyl)-(4R)-hydroxysphinganine
CAS numberNot Available
WeightAverage: 696.1818
Monoisotopic: 695.679160341
InChI KeyGKRXVCWVXYHWOD-KZRDWULCSA-N
InChIInChI=1S/C44H89NO4/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-26-27-29-31-33-35-37-39-43(48)45-41(40-46)44(49)42(47)38-36-34-32-30-28-16-14-12-10-8-6-4-2/h41-42,44,46-47,49H,3-40H2,1-2H3,(H,45,48)/t41-,42+,44-/m0/s1
IUPAC NameN-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]hexacosanamide
Traditional IUPAC NameN-hexacosanoylphytosphingosine
Chemical FormulaC44H89NO4
SMILES[H][C@@](O)([C@H](O)CCCCCCCCCCCCCC)[C@]([H])(CO)NC(=O)CCCCCCCCCCCCCCCCCCCCCCCCC
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 Solubility3.8e-05 g/LALOGPS
logP10.02ALOGPS
logP14.44ChemAxon
logS-7.3ALOGPS
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 Count41ChemAxon
Refractivity212.18 m³·mol⁻¹ChemAxon
Polarizability95.98 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 Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
6750 ± 150 umol/L SD media with 2% raffinose37 oCBY4741PMID: 19174513
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00mk-0005009000-2756de8f0da56e85afccJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0nti-9227804000-109fb26b06482c440616JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uds-7937503000-ddf573884fa37cab40c8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0021309000-df2a2c7a1ec1415c4d8dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4u-2055903000-65e55d4d03be58bc1a66JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9133000000-cbf8d2b8773728cdeb01JSpectraViewer
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 ID52980
HMDB IDNot Available
Pubchem Compound ID10417280
Kegg IDNot Available
ChemSpider IDNot Available
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available