Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB001481
Identification
Name: PE(16:1(9Z)/17:0)
Description:PE(16:1(9Z)/17:0) 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(16:1(9Z)/17:0), in particular, consists of one 9Z-hexadecenoyl chain to the C-1 atom, and one heptadecanoyl 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
Synonyms:
  • 1-(9Z-hexadecenoyl)-2-heptadecanoyl-glycero-3-phosphoethanolamine
  • 1-(9Z-hexadecenoyl)-2-margaroyl-sn-glycero-3-phosphoethanolamine
  • 1-palmitoleoyl-2-heptadecanoyl-sn-glycero-3-phosphoethanolamine
  • GPEtn(16:1/17:0)
  • GPEtn(33:1)
  • PE(16:1/17:0)
  • PE(33:1)
  • Phophatidylethanolamine(16:1/17:0)
  • Phophatidylethanolamine(33:1)
Chemical Formula: C38H74NO8P
Average Molecular Weight: 703.9698
Monoisotopic Molecular Weight: 703.515204861
InChI Key: WSLONBAGRNPTKG-ZYODFBQNSA-N
InChI:InChI=1S/C38H74NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-38(41)47-36(35-46-48(42,43)45-33-32-39)34-44-37(40)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h14,16,36H,3-13,15,17-35,39H2,1-2H3,(H,42,43)/b16-14-/t36-/m1/s1
CAS number: Not Available
IUPAC Name:(2-aminoethoxy)[(2R)-2-(heptadecanoyloxy)-3-[(9Z)-hexadec-9-enoyloxy]propoxy]phosphinic acid
Traditional IUPAC Name: 2-aminoethoxy((2R)-2-(heptadecanoyloxy)-3-[(9Z)-hexadec-9-enoyloxy]propoxy)phosphinic acid
SMILES:[H]\C(CCCCCC)=C(/[H])CCCCCCCC(=O)OC[C@]([H])(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCCCCC
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
Substituents
  • 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
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility8.3e-05 mg/mLALOGPS
logP8.23ALOGPS
logP10.53ChemAxon
logS-6.9ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area134.38 Å2ChemAxon
Rotatable Bond Count39ChemAxon
Refractivity196.72 m3·mol-1ChemAxon
Polarizability85.44 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9040200100-2f7661965268b50f6058View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9140001000-42ae2f327c8e4b632605View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9162010000-419d4e7c39c1b7159e23View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0190201100-f1233930dc1f13c7672bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ug3-4390100000-73477f20b77c91b270a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9220000000-303cd1028bfb168bf1c1View in MoNA
References
References:
  • Ames, G. F. (1968). "Lipids of Salmonella typhimurium and Escherichia coli: structure and metabolism." J Bacteriol 95:833-843. Pubmed: 4868364
  • 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. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID52924224
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in phosphatidylserine decarboxylase activity
Specific function:
Phosphatidyl-L-serine = phosphatidylethanolamine + CO(2)
Gene Name:
psd
Locus Tag:
PA4957
Molecular weight:
32 kDa
Reactions
Phosphatidyl-L-serine = phosphatidylethanolamine + CO(2).

Transporters

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:
mlaE
Locus Tag:
PA4455
Molecular weight:
28.4 kDa