PE(17:0/17:0) (PAMDB001431)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB001431
Identification
Name: PE(17:0/17:0)
Description:PE(17:0/17:0) 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 positions. PE(17:0/17:0), in particular, consists of two heptadecanoyl chains at positions C-1 and C-2. 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
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 1,2-diheptadecanoyl-rac-glycero-3-phosphoethanolamine
  • 1,2-dimargaroyl-rac-glycero-3-phosphoethanolamine
  • GPEtn(17:0/17:0)
  • GPEtn(34:0)
  • Heptadecanoate
  • Heptadecanoate, 1-[[[(2-aminoethoxy)hydroxyphosphinyl]oxy]methyl]-1,2-ethanediyl esterl-a-phosphatidylethanolamine, diheptadecanoylp8664_sigma
  • Heptadecanoate, 1-[[[(2-aminoethoxy)hydroxyphosphinyl]oxy]methyl]-1,2-ethanediyl esterL-alpha-phosphatidylethanolamine, diheptadecanoylP8664_SIGMA
  • Heptadecanoate, 1-[[[(2-aminoethoxy)hydroxyphosphinyl]oxy]methyl]-1,2-ethanediyl esterl-α-phosphatidylethanolamine, diheptadecanoylp8664_sigma
  • Heptadecanoic acid
  • Heptadecanoic acid, 1-[[[(2-aminoethoxy)hydroxyphosphinyl]oxy]methyl]-1,2-ethanediyl esterl-a-phosphatidylethanolamine, diheptadecanoylp8664_sigma
  • Heptadecanoic acid, 1-[[[(2-aminoethoxy)hydroxyphosphinyl]oxy]methyl]-1,2-ethanediyl esterL-alpha-phosphatidylethanolamine, diheptadecanoylP8664_SIGMA
  • Heptadecanoic acid, 1-[[[(2-aminoethoxy)hydroxyphosphinyl]oxy]methyl]-1,2-ethanediyl esterl-α-phosphatidylethanolamine, diheptadecanoylp8664_sigma
  • Margarate
  • Margaric acid
  • PE(34:0)
  • Phophatidylethanolamine(17:0/17:0)
  • Phophatidylethanolamine(34:0)
Chemical Formula: C39H78NO8P
Average Molecular Weight: 720.026
Monoisotopic Molecular Weight: 719.546505474
InChI Key: YSFFAUPDXKTJMR-DIPNUNPCSA-N
InChI:InChI=1S/C39H78NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-38(41)45-35-37(36-47-49(43,44)46-34-33-40)48-39(42)32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h37H,3-36,40H2,1-2H3,(H,43,44)/t37-/m1/s1
CAS number: Not Available
IUPAC Name:(2-aminoethoxy)[(2R)-2,3-bis(heptadecanoyloxy)propoxy]phosphinic acid
Traditional IUPAC Name: 2-aminoethoxy((2R)-2,3-bis(heptadecanoyloxy)propoxy)phosphinic acid
SMILES:[H][C@@](COC(=O)CCCCCCCCCCCCCCCC)(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
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Organic oxide
  • Organic zwitterion
  • Organic salt
  • Hydrocarbon derivative
  • 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 Solubility7.25e-05 mg/mLALOGPS
logP8.55ALOGPS
logP11.34ChemAxon
logS-7ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area134.38 Å2ChemAxon
Rotatable Bond Count41ChemAxon
Refractivity200.21 m3·mol-1ChemAxon
Polarizability89.38 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
PS(17:0/17:0) + Hydrogen ion > Carbon dioxide + PE(17:0/17:0)
Pathways:
Spectra
Spectra:
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 ID5092815
Kegg IDNot Available
ChemSpider ID4268713
Wikipedia IDNot Available
BioCyc IDCPD-7830
EcoCyc IDCPD-7830

Enzymes

Protein Details
• Phosphatidylserine decarboxylase proenzyme
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

Protein Details
• Probable phospholipid ABC transporter permease protein mlaE
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