Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB002009
Name: PE(15:0/17:0cycw7c)
Description:PE(15:0/17:0cycw7c) 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(15:0/17:0cycw7c), in particular, consists of one pentadecanoyl chain to the C-1 atom, and one heptadec-9-10-cyclo-anoyl 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.
  • 1-pentadecanoyl-2-heptadec-9-10-cyclo-anoyl-sn-glycero-3-phosphoethanolamine
  • 1-pentadecanoyl-2-heptadec-cyclopropanol-sn-glycero-3-phosphoethanolamine
  • 1-pentadecanoyl-2-NULL-sn-glycero-3-phosphoethanolamine
  • GPEtn(15:0/17:0)
  • GPEtn(32:0)
  • PE(15:0/17:0)
  • PE(32:0)
  • Phophatidylethanolamine(15:0/17:0)
  • Phophatidylethanolamine(32:0)
Chemical Formula: C37H72NO8P
Average Molecular Weight: 689.9432
Monoisotopic Molecular Weight: 689.499554797
CAS number: Not Available
IUPAC Name:(2-aminoethoxy)[(2R)-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-3-(pentadecanoyloxy)propoxy]phosphinic acid
Traditional IUPAC Name: 2-aminoethoxy(2R)-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-3-(pentadecanoyloxy)propoxyphosphinic 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
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Amine
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Aliphatic homomonocyclic compound
Molecular Framework Aliphatic homomonocyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Melting point: Not Available
Experimental Properties:
Predicted Properties
Water Solubility7.26e-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 Count37ChemAxon
Refractivity189.1 m3·mol-1ChemAxon
Polarizability83.57 Å3ChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Water + PS(15:0/19:iso) > Carbon dioxide + PE(15:0/17:0cycw7c)
PS(15:0/19:iso) + Hydrogen ion > PE(15:0/17:0cycw7c) + Coenzyme A
PS(17:0/16:0) + Hydrogen ion > PE(15:0/17:0cycw7c) + Carbon dioxide
PS(16:0/17:0) + Hydrogen ion > PE(15:0/17:0cycw7c) + Carbon dioxide
PG(14:0/14:0) + PE(15:0/17:0cycw7c) > Ethanolamine + CL(14:0/15:0cyclo/17:0cycw7c/14:0)
PG(15:0/16:1) + PE(15:0/17:0cycw7c) > Ethanolamine + CL(15:0cyclo/15:0cyclo/16:0/17:0cycw7c)
PG(15:0/16:1) + PE(15:0/17:0cycw7c) > CL(15:0cyclo/15:0cyclo/16:1(9Z)/17:0cycw7c) + Ethanolamine
PE(15:0/17:0cycw7c) + PG(15:0/16:1) > Ethanolamine + CL(15:0cyclo/15:0cyclo/17:0cycw7c/16:0)
PG(15:0/16:1) + PE(15:0/17:0cycw7c) > Ethanolamine + CL(15:0cyclo/15:0cyclo/17:0cycw7c/16:1(9Z))
PE(15:0/17:0cycw7c) + PG(15:0/17:0cycw7c) > CL(15:0cyclo/15:0cyclo/17:0cycw7c/17:0cycw7c) + Ethanolamine
PE(15:0/17:0cycw7c) + PG(15:0/16:1) > CL(15:0cyclo/16:0/15:0cyclo/17:0cycw7c) + Ethanolamine
PE(15:0/17:0cycw7c) + PG(15:0/16:1) > Ethanolamine + CL(15:0cyclo/16:0/17:0cycw7c/15:0cyclo)
PG(16:0/16:0) + PE(15:0/17:0cycw7c) > Ethanolamine + CL(15:0cyclo/16:0/16:0/17:0cycw7c)
PG(16:0/16:0) + PE(15:0/17:0cycw7c) > Ethanolamine + CL(15:0cyclo/16:0/17:0cycw7c/16:0)
PE(15:0/17:0cycw7c) + PG(15:0/16:1) > Ethanolamine + CL(15:0cyclo/16:1(9Z)/15:0cyclo/17:0cycw7c)
PE(15:0/17:0cycw7c) + PG(16:1(9Z)/16:1(9Z)) > Ethanolamine + CL(15:0cyclo/16:1(9Z)/16:1(9Z)/17:0cycw7c)
PE(15:0/17:0cycw7c) + PG(15:0/16:1) > Ethanolamine + CL(15:0cyclo/16:1(9Z)/17:0cycw7c/15:0cyclo)
PG(16:1(9Z)/16:1(9Z)) + PE(15:0/17:0cycw7c) > Ethanolamine + CL(15:0cyclo/16:1(9Z)/17:0cycw7c/16:1(9Z))
PE(15:0/17:0cycw7c) + PG(14:0/14:0) > Ethanolamine + CL(15:0cyclo/17:0cycw7c/14:0/14:0)
PG(15:0/17:0cycw7c) + PE(15:0/17:0cycw7c) > Ethanolamine + CL(15:0cyclo/17:0cycw7c/15:0cyclo/17:0cycw7c)
PG(16:0/16:0) + PE(15:0/17:0cycw7c) > Ethanolamine + CL(15:0cyclo/17:0cycw7c/16:0/16:0)
PE(15:0/17:0cycw7c) + PG(16:1(9Z)/16:1(9Z)) > Ethanolamine + CL(15:0cyclo/17:0cycw7c/16:1(9Z)/16:1(9Z))
PG(15:0/17:0cycw7c) + PE(15:0/17:0cycw7c) > Ethanolamine + CL(15:0cyclo/17:0cycw7c/17:0cycw7c/14:0)
PE(15:0/17:0cycw7c) + PG(15:0/17:0cycw7c) > Ethanolamine + CL(15:0cyclo/17:0cycw7c/17:0cycw7c/15:0cyclo)
PE(15:0/17:0cycw7c) + PG(17:0/19:0) > Ethanolamine + CL(15:0cyclo/17:0cycw7c/17:0cycw7c/19:0cycv8c)
PG(18:1(9Z)/18:1(9Z)) + PE(15:0/17:0cycw7c) > Ethanolamine + CL(15:0cyclo/17:0cycw7c/18:1(9Z)/18:1(9Z))
PG(17:0/19:0) + PE(15:0/17:0cycw7c) > Ethanolamine + CL(15:0cyclo/17:0cycw7c/19:0cycv8c/17:0cycw7c)
PE(15:0/17:0cycw7c) + PG(18:1(9Z)/18:1(9Z)) > Ethanolamine + CL(15:0cyclo/18:1(9Z)/17:0cycw7c/18:1(9Z))
PG(18:1(9Z)/18:1(9Z)) + PE(15:0/17:0cycw7c) > Ethanolamine + CL(15:0cyclo/18:1(9Z)/18:1(9Z)/17:0cycw7c)
PE(15:0/17:0cycw7c) + PG(15:0/19:iso) > Ethanolamine + CL(15:0cyclo/19:0cycv8c/17:0cycw7c/15:0cyclo)
PG(17:0/19:0) + PE(15:0/17:0cycw7c) > Ethanolamine + CL(15:0cyclo/19:0cycv8c/17:0cycw7c/17:0cycw7c)
PG(15:0/16:1) + PE(15:0/17:0cycw7c) > Ethanolamine + CL(16:0/15:0cyclo/15:0cyclo/17:0cycw7c)
PG(16:0/16:0) + PE(15:0/17:0cycw7c) > Ethanolamine + CL(16:0/15:0cyclo/16:0/17:0cycw7c)
PG(15:0/16:1) + PE(15:0/17:0cycw7c) > Ethanolamine + CL(16:0/15:0cyclo/17:0cycw7c/15:0cyclo)
PE(15:0/17:0cycw7c) + PG(16:0/16:0) > Ethanolamine + CL(16:0/15:0cyclo/17:0cycw7c/16:0)
PG(16:0/16:0) + PE(15:0/17:0cycw7c) > CL(16:0/16:0/16:0/17:0cycw7c) + Ethanolamine
PG(16:0/16:0) + PE(15:0/17:0cycw7c) > Ethanolamine + CL(16:0/16:0/17:0cycw7c/15:0cyclo)
PG(16:0/16:0) + PE(15:0/17:0cycw7c) > Ethanolamine + CL(16:0/16:0/17:0cycw7c/16:0)
PG(16:1(9Z)/16:1(9Z)) + PE(15:0/17:0cycw7c) > Ethanolamine + CL(16:0/16:1(9Z)/16:1(9Z)/17:0cycw7c)
PG(16:1(9Z)/16:1(9Z)) + PE(15:0/17:0cycw7c) > Ethanolamine + CL(16:0/16:1(9Z)/17:0cycw7c/16:1(9Z))
PE(15:0/17:0cycw7c) + PG(16:1(9Z)/16:1(9Z)) > CL(16:0/17:0cycw7c/16:1(9Z)/16:1(9Z)) + Ethanolamine
PG(18:1(9Z)/18:1(9Z)) + PE(15:0/17:0cycw7c) > Ethanolamine + CL(16:0/17:0cycw7c/18:1(9Z)/18:1(9Z))
PG(18:1(9Z)/18:1(9Z)) + PE(15:0/17:0cycw7c) > CL(16:0/18:1(9Z)/17:0cycw7c/18:1(9Z)) + Ethanolamine
PE(15:0/17:0cycw7c) + PG(18:1(9Z)/18:1(9Z)) > Ethanolamine + CL(16:0/18:1(9Z)/18:1(9Z)/17:0cycw7c)
PG(16:1(9Z)/16:1(9Z)) + PE(15:0/17:0cycw7c) > Ethanolamine + CL(16:1(9Z)/15:0cyclo/16:1(9Z)/17:0cycw7c)
PE(15:0/17:0cycw7c) + PG(15:0/16:1) > Ethanolamine + CL(16:1(9Z)/15:0cyclo/17:0cycw7c/15:0cyclo)
PG(16:1(9Z)/16:1(9Z)) + PE(15:0/17:0cycw7c) > Ethanolamine + CL(16:1(9Z)/15:0cyclo/17:0cycw7c/16:1(9Z))
PG(16:1(9Z)/16:1(9Z)) + PE(15:0/17:0cycw7c) > Ethanolamine + CL(16:1(9Z)/16:0/16:1(9Z)/17:0cycw7c)
PG(16:1(9Z)/16:1(9Z)) + PE(15:0/17:0cycw7c) > CL(16:1(9Z)/16:0/17:0cycw7c/16:1(9Z)) + Ethanolamine
PG(16:1(9Z)/16:1(9Z)) + PE(15:0/17:0cycw7c) > Ethanolamine + CL(16:1(9Z)/16:1(9Z)/17:0cycw7c/15:0cyclo)
PG(16:1(9Z)/16:1(9Z)) + PE(15:0/17:0cycw7c) > Ethanolamine + CL(16:1(9Z)/16:1(9Z)/17:0cycw7c/16:0)
PG(14:0/14:0) + PE(15:0/17:0cycw7c) > CL(17:0cycw7c/15:0cyclo/14:0/14:0) + Ethanolamine
PG(15:0/17:0cycw7c) + PE(15:0/17:0cycw7c) > CL(17:0cycw7c/15:0cyclo/17:0cycw7c/15:0cyclo) + Ethanolamine
PG(17:0/19:0) + PE(15:0/17:0cycw7c) > CL(17:0cycw7c/15:0cyclo/17:0cycw7c/19:0cycv8c) + Ethanolamine
PE(15:0/17:0cycw7c) + PG(17:0/19:0) > CL(17:0cycw7c/15:0cyclo/19:0cycv8c/17:0cycw7c) + Ethanolamine
PG(18:1(9Z)/18:1(9Z)) + PE(15:0/17:0cycw7c) > Ethanolamine + CL(18:1(9Z)/16:0/18:1(9Z)/17:0cycw7c)
PG(18:1(9Z)/18:1(9Z)) + PE(15:0/17:0cycw7c) > Ethanolamine + CL(18:1(9Z)/16:0/17:0cycw7c/18:1(9Z))
PE(15:0/17:0cycw7c) + PG(18:1(9Z)/18:1(9Z)) > CL(18:1(9Z)/18:1(9Z)/17:0cycw7c/15:0cyclo) + Ethanolamine
PG(18:1(9Z)/18:1(9Z)) + PE(15:0/17:0cycw7c) > CL(18:1(9Z)/18:1(9Z)/17:0cycw7c/16:0) + Ethanolamine
PE(15:0/17:0cycw7c) + PG(15:0/19:iso) > CL(19:0cycv8c/15:0cyclo/17:0cycw7c/15:0cyclo) + Ethanolamine

Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9140200100-0fa7d9910730311c6e02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9140001000-8702fc3883cbd2b3322cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9260011000-b420ade01114196c39d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dl-0190201100-bc0cb3fb2cb95d8178faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-5490100000-8808de1230947eaf53d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9220000000-b398318b928fdbf2fd22View 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
  • Oursel, D., Loutelier-Bourhis, C., Orange, N., Chevalier, S., Norris, V., Lange, C. M. (2007). "Lipid composition of membranes of Escherichia coli by liquid chromatography/tandem mass spectrometry using negative electrospray ionization." Rapid Commun Mass Spectrom 21:1721-1728. Pubmed: 17477452
  • 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:
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available


General function:
Involved in phosphatidylserine decarboxylase activity
Specific function:
Phosphatidyl-L-serine = phosphatidylethanolamine + CO(2)
Gene Name:
Locus Tag:
Molecular weight:
32 kDa
Phosphatidyl-L-serine = phosphatidylethanolamine + CO(2).
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
Catalyzes the reversible phosphatidyl group transfer from one phosphatidylglycerol molecule to another to form cardiolipin (CL) (diphosphatidylglycerol) and glycerol. Affects resistance to the gyrase inhibitor novobiocin
Gene Name:
Locus Tag:
Molecular weight:
54.6 kDa
2 Phosphatidylglycerol = diphosphatidylglycerol + glycerol.
General function:
Involved in catalytic activity
Specific function:
Catalyzes, in vitro, the phosphatidyl group transfer from one phosphatidylglycerol molecule to another to form cardiolipin (CL) (diphosphatidylglycerol) and glycerol. Can also catalyze phosphatidyl group transfer to water to form phosphatidate. Catalyzes little, if any, cardiolipin synthesis in vivo, even when the expression level is very high
Gene Name:
Locus Tag:
Molecular weight:
46.5 kDa
2 Phosphatidylglycerol = diphosphatidylglycerol + glycerol.


General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Part of the ABC transporter complex mlaFEDB that actively prevents phospholipid accumulation at the cell surface. Probably maintains lipid asymmetry in the outer membrane by retrograde trafficking of phospholipids from the outer membrane to the inner membrane
Gene Name:
Locus Tag:
Molecular weight:
28.4 kDa