Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB006221
Name: PE(14:0/18:1(9Z))
Description:PE(14:0/18:1(9Z)) 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(14:0/18:1(9Z)), in particular, consists of one tetradecanoyl chain to the C-1 atom, and one 9Z-octadecenoyl 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.
Synonyms:Not Available
Chemical Formula: C37H72NO8P
Average Molecular Weight: 689.9432
Monoisotopic Molecular Weight: 689.499554797
CAS number: Not Available
IUPAC Name:(2-aminoethoxy)[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(tetradecanoyloxy)propoxy]phosphinic acid
Traditional IUPAC Name: 2-aminoethoxy((2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(tetradecanoyloxy)propoxy)phosphinic acid
Chemical Taxonomy
Taxonomy DescriptionThis compound 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.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Glycerophospholipids
Sub ClassGlycerophosphoethanolamines
Direct Parent Phosphatidylethanolamines
Alternative Parents
  • Diacylglycero-3-phosphoethanolamine
  • Phosphoethanolamine
  • Dialkyl phosphate
  • Fatty acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Not Available
Melting point: Not Available
Experimental Properties:
Predicted Properties
Water Solubility9.92e-05 mg/mLALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area134.38 Å2ChemAxon
Rotatable Bond Count38ChemAxon
Refractivity192.12 m3·mol-1ChemAxon
Polarizability83.63 Å3ChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
PS(14:0/19:0) + Hydrogen ion > PE(14:0/18:1(9Z)) + Carbon dioxide
PS(14:0/18:1(9Z)) + Hydrogen ion > PE(14:0/18:1(9Z)) + Carbon dioxide
PE(14:0/18:1(9Z)) + PG(14:0/16:0) > Ethanolamine + CL(14:0/16:0/14:0/18:1(9Z))
PE(14:0/18:1(9Z)) + PG(14:0/16:0) > Ethanolamine + CL(14:0/16:0/18:1(9Z)/14:0)
PG(14:0/14:0) + PE(14:0/18:1(9Z)) > Ethanolamine + CL(14:0/18:1(9Z)/14:0/14:0)
PG(14:0/16:0) + PE(14:0/18:1(9Z)) > Ethanolamine + CL(16:0/14:0/14:0/18:1(9Z))
PG(16:0/16:0) + PE(14:0/18:1(9Z)) > Ethanolamine + CL(16:0/16:0/14:0/18:1(9Z))
PG(16:0/16:0) + PE(14:0/18:1(9Z)) > Ethanolamine + CL(16:0/16:0/18:1(9Z)/14:0)
PG(16:0/16:0) + PE(14:0/18:1(9Z)) > Ethanolamine + CL(16:0/18:1(9Z)/14:0/16:0)
PG(16:0/16:0) + PE(14:0/18:1(9Z)) > Ethanolamine + CL(16:0/18:1(9Z)/16:0/14:0)
PG(16:1(9Z)/16:1(9Z)) + PE(14:0/18:1(9Z)) > Ethanolamine + CL(16:1(9Z)/16:1(9Z)/14:0/18:1(9Z))
PG(16:1(9Z)/16:1(9Z)) + PE(14:0/18:1(9Z)) > Ethanolamine + CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/14:0)
PE(14:0/18:1(9Z)) + PG(16:1(9Z)/16:1(9Z)) > Ethanolamine + CL(16:1(9Z)/18:1(9Z)/14:0/16:1(9Z))
PE(14:0/18:1(9Z)) + PG(16:1(9Z)/16:1(9Z)) > Ethanolamine + CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/14:0)
PE(14:0/18:1(9Z)) + PG(18:1(9Z)/16:0) > Ethanolamine + CL(18:1(9Z)/16:0/14:0/18:1(9Z))
PE(14:0/18:1(9Z)) + PG(18:1(9Z)/16:1(9Z)) > Ethanolamine + CL(18:1(9Z)/16:1(9Z)/14:0/18:1(9Z))
PG(18:1(9Z)/19:0cycv8c) + PE(14:0/18:1(9Z)) > Ethanolamine + CL(18:1(9Z)/19:0cycv8c/14:0/18:1(9Z))
PE(14:0/18:1(9Z)) + PG(18:1(9Z)/18:1(9Z)) > CL(18:1(9Z)/18:1(9Z)/14:0/18:1(9Z)) + Ethanolamine
PE(14:0/18:1(9Z)) + PG(14:0/17:0cycw7c) > CL(18:1(9Z)/14:0/17:0cycw7c/14:0) + Ethanolamine
PE(14:0/18:1(9Z)) + PG(19:0cycv8c/18:1(9Z)) > Ethanolamine + CL(19:0cycv8c/18:1(9Z)/14:0/18:1(9Z))
Pathways: Not Available
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9140202000-e636316e685ec74b4564View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9240001000-ce2ccbe38cfcb12976e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9270021000-4f988712c23806150d63View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-0190203000-6355a714ae227d438378View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-5490100000-66f6955ec06649610111View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9220000000-ec5ce3b3cd40cd442cfdView in MoNA
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. Thesis. Villanova University: U.S.A
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
Pubchem Compound ID52924944
Kegg IDC00350
ChemSpider ID24768333
Wikipedia IDNot Available
BioCyc IDNot Available