PE(14:0/18:0) (YMDB14118)

Identification
YMDB IDYMDB14118
NamePE(14:0/18:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPE(14:0/18:0) is a phosphatidylethanolamine. It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 atoms. PE(14:0/18:0), in particular, consists of one tetradecanoyl chain to the C-1 atom, and one octadecanoyl to the C-2 atom. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • Phophatidylethanolamine(14:0/18:0)
  • PE(32:0)
  • 1-Myristoyl-2-stearoyl-sn-glycero-3-phosphoethanolamine
  • GPEtn(32:0)
  • GPEtn(14:0/18:0)
  • Phophatidylethanolamine(32:0)
  • 1-Tetradecanoyl-2-octadecanoyl-sn-glycero-3-phosphoethanolamine
  • PE(14:0/18:0)
CAS numberNot Available
WeightAverage: 691.972
Monoisotopic: 691.515205345
InChI KeyAUSLLMXXJBCZGL-PGUFJCEWSA-N
InChIInChI=1S/C37H74NO8P/c1-3-5-7-9-11-13-15-16-17-18-20-22-24-26-28-30-37(40)46-35(34-45-47(41,42)44-32-31-38)33-43-36(39)29-27-25-23-21-19-14-12-10-8-6-4-2/h35H,3-34,38H2,1-2H3,(H,41,42)/t35-/m1/s1
IUPAC Name(2-aminoethoxy)[(2R)-2-(octadecanoyloxy)-3-(tetradecanoyloxy)propoxy]phosphinic acid
Traditional IUPAC Name2-aminoethoxy((2R)-2-(octadecanoyloxy)-3-(tetradecanoyloxy)propoxy)phosphinic acid
Chemical FormulaC37H74NO8P
SMILES[H][C@@](COC(=O)CCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCCCCCC
Chemical Taxonomy
Description belongs to the class of organic compounds known as phosphatidylethanolamines. These are glycerophosphoetahnolamines in which two fatty acids are bonded to the glycerol moiety through ester linkages.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoethanolamines
Direct ParentPhosphatidylethanolamines
Alternative Parents
Substituents
  • Diacylglycero-3-phosphoethanolamine
  • Phosphoethanolamine
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Primary amine
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility9.4e-05 g/LALOGPS
logP8.09ALOGPS
logP10.45ChemAxon
logS-6.9ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area134.38 ŲChemAxon
Rotatable Bond Count39ChemAxon
Refractivity191 m³·mol⁻¹ChemAxon
Polarizability85.09 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Endoplasmic reticulum
  • Mitochondria
Organoleptic PropertiesNot Available
SMPDB Pathways
Phosphatidylcholine biosynthesis PC(14:0/18:0)PW002911 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
PE(14:0/18:0) + S-Adenosyl-L-methionine → PE-NMe(14:0/18:0) + hydron + S-Adenosylhomocysteine
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0030009000-77898e5f947e9886f85dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0030009000-77898e5f947e9886f85dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003u-0190303000-25cf0e7e688a39eabf0bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000019000-814aefc198261f6d39f6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udl-0011697000-6586f57e237c949468f5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0011693000-a856f7dac6b6572c1779JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000010900-bb7978dcbee6464346dfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03k9-0000022900-6efdc1241c22750b2501JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0101119100-d2d0f98e110799bce34bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000019000-9ed53d8418cab57ddd34JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udl-0011697000-2a7126832e1c5328a1f1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0011693000-c77ae7c5971d8bc6285fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0030009000-7afb12c6b041105990c6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0030009000-7afb12c6b041105990c6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003u-0190303000-135217e3eb23caae22ecJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Rattray JB, Schibeci A, Kidby DK. (1975). "Lipids of yeasts." Bacteriol Rev. 1975 Sep;39(3):197-231.240350
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB0008826
Pubchem Compound ID49786976
Kegg IDNot Available
ChemSpider IDNot Available
FOODB IDFDB026016
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Phosphatidylethanolamine N-methyltransferase
General function:
Involved in phosphatidylethanolamine N-methyltransferas
Specific function:
S-adenosyl-L-methionine + phosphatidylethanolamine = S-adenosyl-L-homocysteine + phosphatidyl-N-methylethanolamine
Gene Name:
PEM1
Uniprot ID:
P05374
Molecular weight:
101203.0
Reactions
S-adenosyl-L-methionine + phosphatidylethanolamine → S-adenosyl-L-homocysteine + phosphatidyl-N-methylethanolamine.