PE(14:1(9Z)/16:0) (YMDB01196)

Identification
YMDB IDYMDB01196
NamePE(14:1(9Z)/16:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPE(14:1(9Z)/16:0) 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(14:1(9Z)/16:0), in particular, consists of one 9Z-tetradecenoyl chain to the C-1 atom, and one hexadecanoyl 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
  • (3-Phosphatidyl)-ethanolamine
  • (3-Phosphatidyl)ethanolamine
  • 1-Acyl-2-acyl-sn-glycero-3-phosphoethanolamine
  • 1-myristoleoyl-2-palmitoyl-sn-glycero-3-phosphoethanolamine
  • 1,2-diacyl-sn-glycero-3-phosphoethanolamine
  • Cephalin
  • GPEtn(14:1/16:0)
  • GPEtn(14:1n5/16:0)
  • GPEtn(14:1w5/16:0)
  • GPEtn(30:1)
  • O-(1-beta-Acyl-2-acyl-sn-glycero-3-phospho)ethanolamine
  • PE(14:1/16:0)
  • PE(14:1n5/16:0)
  • PE(14:1w5/16:0)
  • PE(30:1)
  • Phophatidylethanolamine(14:1/16:0)
  • Phophatidylethanolamine(14:1n5/16:0)
  • Phophatidylethanolamine(14:1w5/16:0)
  • Phophatidylethanolamine(30:1)
  • Phosphatidylethanolamine
  • phosphatidylethanolamines
  • 1-(9Z-Tetradecenoyl)-2-hexadecanoyl-sn-glycero-3-phosphoethanolamine
  • PE(14:1(9Z)/16:0)
CAS numberNot Available
WeightAverage: 661.8901
Monoisotopic: 661.468254669
InChI KeyIXIBEFBSXYIWMP-ALMVXPMNSA-N
InChIInChI=1S/C35H68NO8P/c1-3-5-7-9-11-13-15-16-18-20-22-24-26-28-35(38)44-33(32-43-45(39,40)42-30-29-36)31-41-34(37)27-25-23-21-19-17-14-12-10-8-6-4-2/h10,12,33H,3-9,11,13-32,36H2,1-2H3,(H,39,40)/b12-10-/t33-/m1/s1
IUPAC Name(2-aminoethoxy)[(2R)-2-(hexadecanoyloxy)-3-[(9Z)-tetradec-9-enoyloxy]propoxy]phosphinic acid
Traditional IUPAC Name2-aminoethoxy(2R)-2-(hexadecanoyloxy)-3-[(9Z)-tetradec-9-enoyloxy]propoxyphosphinic acid
Chemical FormulaC35H68NO8P
SMILES[H][C@@](COC(=O)CCCCCCC\C=C/CCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCCCC
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 Solubility0.00014 g/LALOGPS
logP7.48ALOGPS
logP9.2ChemAxon
logS-6.7ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area134.38 ŲChemAxon
Rotatable Bond Count36ChemAxon
Refractivity182.92 m³·mol⁻¹ChemAxon
Polarizability79.75 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
Glycerophospholipid metabolismPW002493 ThumbThumb?image type=greyscaleThumb?image type=simple
Phosphatidylcholine biosynthesis PC(14:1(9Z)/16:0)PW002833 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycerophospholipid metabolismec00564 Map00564
Glycosylphosphatidylinositol(GPI)-anchor biosynthesisec00563 Map00563
SMPDB Reactions
PE(14:1(9Z)/16:0) + S-Adenosyl-L-methionine → PE-NMe(14:1(9Z)/16:0) + hydron + S-Adenosylhomocysteine
KEGG ReactionsNot Available
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
30250 ± 3625 umol/L SD media with 2% raffinose24 oCBY4741PMID: 19174513
Conversion Details Here
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, Negativesplash10-03di-0030009000-8d546e170bd7a2b2deadJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0030009000-8d546e170bd7a2b2deadJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0r4i-0190303000-1fbb58132a75fff2f9d7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000019000-fbd23580b5f8c70a170eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0229-0011697000-1061c71bff9052fe2849JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0011693000-6b3bcfdb4bd4a8a1ce5eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0030009000-5b69cd33db7c3c42a5e9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0030009000-5b69cd33db7c3c42a5e9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0r4i-0190303000-5196cc28466aa465e278JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000019000-79e77b93d9865cb2cb9dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0229-0011697000-eb3576269855a7abc9dbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0011693000-76a6e6138660a0ad9395JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000019000-1cd30130f4f479dca1acJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001l-0000019000-4423687200d2ef3d34d4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0101119000-b371277a3eb57412b862JSpectraViewer
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:
  • 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
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16038
HMDB IDHMDB08857
Pubchem Compound ID108229
Kegg IDC00350
ChemSpider ID24768362
FOODB IDFDB026047
WikipediaLecithin
BioCyc IDL-1-PHOSPHATIDYL-ETHANOLAMINE

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.