PE(18:0/16:1(9Z)) (YMDB01205)

Identification
YMDB IDYMDB01205
NamePE(18:0/16:1(9Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPE(18:0/16:1(9Z)) is a phosphatidylethanolamine (PE or GPEtn). 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 at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(18:0/16:1(9Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of palmitoleic acid at the C-2 position. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. 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-stearoyl-2-palmitoleoyl-sn-glycero-3-phosphoethanolamine
  • 1,2-diacyl-sn-glycero-3-phosphoethanolamine
  • Cephalin
  • GPEtn(18:0/16:1)
  • GPEtn(18:0/16:1n7)
  • GPEtn(18:0/16:1w7)
  • GPEtn(34:1)
  • O-(1-beta-Acyl-2-acyl-sn-glycero-3-phospho)ethanolamine
  • PE(18:0/16:1)
  • PE(18:0/16:1n7)
  • PE(18:0/16:1w7)
  • PE(34:1)
  • Phophatidylethanolamine(18:0/16:1)
  • Phophatidylethanolamine(18:0/16:1n7)
  • Phophatidylethanolamine(18:0/16:1w7)
  • Phophatidylethanolamine(34:1)
  • Phosphatidylethanolamine
  • phosphatidylethanolamines
  • 1-Octadecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphoethanolamine
  • PE(18:0/16:1(9Z))
CAS numberNot Available
WeightAverage: 717.9964
Monoisotopic: 717.530854925
InChI KeyXQWOAWVAWAXMKM-UHGNNPBBSA-N
InChIInChI=1S/C39H76NO8P/c1-3-5-7-9-11-13-15-17-18-20-21-23-25-27-29-31-38(41)45-35-37(36-47-49(43,44)46-34-33-40)48-39(42)32-30-28-26-24-22-19-16-14-12-10-8-6-4-2/h14,16,37H,3-13,15,17-36,40H2,1-2H3,(H,43,44)/b16-14-/t37-/m1/s1
IUPAC Name(2-aminoethoxy)[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(octadecanoyloxy)propoxy]phosphinic acid
Traditional IUPAC Name2-aminoethoxy((2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(octadecanoyloxy)propoxy)phosphinic acid
Chemical FormulaC39H76NO8P
SMILES[H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCC\C=C/CCCCCC
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 Solubility6.9e-05 g/LALOGPS
logP8.44ALOGPS
logP10.98ChemAxon
logS-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 Count40ChemAxon
Refractivity201.32 m³·mol⁻¹ChemAxon
Polarizability87.65 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
KEGG Pathways
Glycerophospholipid metabolismec00564 Map00564
Glycosylphosphatidylinositol(GPI)-anchor biosynthesisec00563 Map00563
SMPDB ReactionsNot Available
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, Negativesplash10-014i-0030000900-1d55c34c613ed752ae23JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0030000900-1d55c34c613ed752ae23JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uz9-0190300300-17ba9d13223ca070e431JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000010900-6f573d993dec08dd3c88JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00or-0003690700-9f2871fa29874bca4f07JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0003690300-a87449819311c699e0b7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000010900-4384bbfae935cffc95d1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0007-0000022900-ad5dbee97cbecdd5b53aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0100319100-92cc1db712e5b21d4dc0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000010900-371a20b1ba3d80b384eeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00or-0003690700-e89184f9dea01a79fdc4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0003690300-669f6c1c361b0b712d73JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0030000900-4891e765e8769ea0f50dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0030000900-4891e765e8769ea0f50dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uz9-0190300300-f840baf0258c45155c7fJSpectraViewer
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 IDHMDB08990
Pubchem Compound ID108229
Kegg IDC00350
ChemSpider ID24768474
FOODB IDFDB026180
WikipediaLecithin
BioCyc IDL-1-PHOSPHATIDYL-ETHANOLAMINE