PE(17:0/14:0) (PAMDB001444)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB001444
Identification
Name: PE(17:0/14:0)
Description:PE(17:0/14:0) 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(17:0/14:0), in particular, consists of one heptadecanoyl chain to the C-1 atom, and one tetradecanoyl 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
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 1-heptadecanoyl-2-myristoyl-sn-glycero-3-phosphoethanolamine
  • 1-heptadecanoyl-2-tetradecanoyl-glycero-3-phosphoethanolamine
  • 1-margaroyl-2-tetradecanoyl-sn-glycero-3-phosphoethanolamine
  • GPEtn(17:0/14:0)
  • GPEtn(31:0)
  • PE(31:0)
  • Phophatidylethanolamine(17:0/14:0)
  • Phophatidylethanolamine(31:0)
Chemical Formula: C36H72NO8P
Average Molecular Weight: 677.9325
Monoisotopic Molecular Weight: 677.499554797
InChI Key: LDXXKNJVIYWBQC-UUWRZZSWSA-N
InChI:InChI=1S/C36H72NO8P/c1-3-5-7-9-11-13-15-16-17-19-20-22-24-26-28-35(38)42-32-34(33-44-46(40,41)43-31-30-37)45-36(39)29-27-25-23-21-18-14-12-10-8-6-4-2/h34H,3-33,37H2,1-2H3,(H,40,41)/t34-/m1/s1
CAS number: Not Available
IUPAC Name:(2-aminoethoxy)[(2R)-3-(heptadecanoyloxy)-2-(tetradecanoyloxy)propoxy]phosphinic acid
Traditional IUPAC Name: 2-aminoethoxy((2R)-3-(heptadecanoyloxy)-2-(tetradecanoyloxy)propoxy)phosphinic acid
SMILES:[H][C@@](COC(=O)CCCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCC
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 Solubility0.000106 mg/mLALOGPS
logP7.84ALOGPS
logP10.01ChemAxon
logS-6.8ALOGPS
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
Refractivity186.4 m3·mol-1ChemAxon
Polarizability82.97 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
PS(17:0/14:0) + Hydrogen ion > PE(17:0/14:0) + Carbon dioxide
PE(17:0/14:0) + PG(16:0/14:0) > Ethanolamine + CL(19:0cycv8c/18:1(9Z)/14:0/14:0)
PE(17:0/14:0) + PG(14:0/14:0) > Ethanolamine + CL(18:1(9Z)/14:0/17:0cycw7c/14:0)
PE(17:0/14:0) + PG(16:0/14:0) > Ethanolamine + CL(17:0cycw7c/17:0cycw7c/14:0/17:0cycw7c)
PE(17:0/14:0) + PG(16:0/14:0) > Ethanolamine + CL(17:0cycw7c/17:0cycw7c/17:0cycw7c/14:0)
PG(14:0/14:0) + PE(17:0/14:0) > Ethanolamine + CL(14:0/18:1(9Z)/14:0/17:0cycw7c)
PE(17:0/14:0) + PG(16:1(9Z)/16:1(9Z)) > Ethanolamine + CL(16:1(9Z)/18:1(9Z)/17:0cycw7c/16:1(9Z))
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9040102000-76f7c3af889a3c8f75deView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9130001000-2fa01ea04a6f833a3f89View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9042030000-67e5ec9d710d26b7cf64View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gdi-0190203000-93a356fc54cc7cdfa825View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00or-4390100000-d17f09a46517e4633a97View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9220000000-58e0105254d4373c7cacView 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 ID52924243
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

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