Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB006223
Identification
Name: PE(15:0/15:0)
Description:PE(15:0/15:0) 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(15:0/15:0), in particular, consists of two pentadecanoyl 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
Synonyms:Not Available
Chemical Formula: C35H70NO8P
Average Molecular Weight: 663.906
Monoisotopic Molecular Weight: 663.483904733
InChI Key: SKVKIGSFTGVBOX-MGBGTMOVSA-N
InChI:InChI=1S/C35H70NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-34(37)41-31-33(32-43-45(39,40)42-30-29-36)44-35(38)28-26-24-22-20-18-16-14-12-10-8-6-4-2/h33H,3-32,36H2,1-2H3,(H,39,40)/t33-/m1/s1
CAS number: Not Available
IUPAC Name:(2-aminoethoxy)[(2R)-2,3-bis(pentadecanoyloxy)propoxy]phosphinic acid
Traditional IUPAC Name: 2-aminoethoxy((2R)-2,3-bis(pentadecanoyloxy)propoxy)phosphinic acid
SMILES:[H][C@@](COC(=O)CCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCCC
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 Solubility0.000139 mg/mLALOGPS
logP7.58ALOGPS
logP9.56ChemAxon
logS-6.7ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area134.38 Å2ChemAxon
Rotatable Bond Count37ChemAxon
Refractivity181.8 m3·mol-1ChemAxon
Polarizability81.2 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
PS(16:0/14:1(9Z)) + Hydrogen ion > PE(15:0/15:0) + Carbon dioxide
PE(15:0/15:0) + PG(15:0/16:1) > Ethanolamine + CL(15:0cyclo/15:0cyclo/15:0cyclo/18:1(9Z))
PE(15:0/15:0) + PG(15:0/19:iso) > Ethanolamine + CL(15:0cyclo/15:0cyclo/15:0cyclo/19:0cycv8c)
PG(16:1(9Z)/16:1(9Z)) + PE(15:0/15:0) > Ethanolamine + CL(15:0cyclo/15:0cyclo/16:1(9Z)/16:1(9Z))
PE(15:0/15:0) + PG(15:0/19:iso) > Ethanolamine + CL(15:0cyclo/15:0cyclo/18:1(9Z)/15:0cyclo)
PE(15:0/15:0) + PG(18:1(9Z)/18:1(9Z)) > Ethanolamine + CL(15:0cyclo/15:0cyclo/18:1(9Z)/18:1(9Z))
PE(15:0/15:0) + PG(15:0cyclo/19:iso) > Ethanolamine + CL(15:0cyclo/15:0cyclo/19:0cycv8c/15:0cyclo)
PG(16:1(9Z)/16:1(9Z)) + PE(15:0/15:0) > Ethanolamine + CL(15:0cyclo/16:1(9Z)/15:0cyclo/16:1(9Z))
PG(16:1(9Z)/16:1(9Z)) + PE(15:0/15:0) > Ethanolamine + CL(15:0cyclo/16:1(9Z)/16:1(9Z)/15:0cyclo)
PG(18:1(9Z)/18:1(9Z)) + PE(15:0/15:0) > Ethanolamine + CL(15:0cyclo/18:1(9Z)/15:0cyclo/18:1(9Z))
PG(18:1(9Z)/18:1(9Z)) + PE(15:0/15:0) > Ethanolamine + CL(15:0cyclo/18:1(9Z)/18:1(9Z)/15:0cyclo)
PE(15:0/15:0) + PG(14:0/16:1(9Z)) > Ethanolamine + CL(16:1(9Z)/15:0cyclo/14:0/15:0cyclo)
PE(15:0/15:0) + PG(14:0/16:1(9Z)) > Ethanolamine + CL(16:1(9Z)/15:0cyclo/15:0cyclo/14:0)
PE(15:0/15:0) + PG(16:1(9Z)/17:0) > Ethanolamine + CL(16:1(9Z)/15:0cyclo/15:0cyclo/17:0cycw7c)
PE(15:0/15:0) + PG(16:1(9Z)/18:1(9Z)) > Ethanolamine + CL(16:1(9Z)/15:0cyclo/15:0cyclo/18:1(9Z))
PE(15:0/15:0) + PG(16:1(9Z)/16:1(9Z)) > Ethanolamine + CL(16:1(9Z)/15:0cyclo/16:1(9Z)/15:0cyclo)
PG(16:1(9Z)/18:1(9Z)) + PE(15:0/15:0) > CL(16:1(9Z)/15:0cyclo/18:1(9Z)/15:0cyclo) + Ethanolamine
PG(18:1(9Z)/18:1(9Z)) + PE(15:0/15:0) > Ethanolamine + CL(18:1(9Z)/15:0cyclo/18:1(9Z)/15:0cyclo)
PG(18:1(9Z)/19:iso) + PE(15:0/15:0) > Ethanolamine + CL(18:1(9Z)/15:0cyclo/19:0cycv8c/15:0cyclo)
PE(15:0/15:0) + PG(18:1(11Z)/17:0) > Ethanolamine + CL(18:1(9Z)/15:0cyclo/17:0cycw7c/15:0cyclo)
PE(15:0/15:0) + PG(18:1(9Z)/14:0(3-OH)) > Ethanolamine + CL(18:1(9Z)/15:0cyclo/14:0/15:0cyclo)
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9120202000-cb57d81a0d28f0f5ef40View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9220001000-6a559a5aad641ea1bc6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9250030000-dcbd9d8138732ed47f09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dl-1290305000-aa8fcf418de3df039c35View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0096-6591101000-14626ff7a7e64bc2800cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9210000000-4f6c0c30aacbc3cf07eaView in MoNA
References
References:
  • 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 IDHMDB08889
Pubchem Compound ID9546807
Kegg IDC00350
ChemSpider ID7825757
Wikipedia IDNot Available
BioCyc IDNot Available