Record Information
Version2.0
Creation Date2015-09-08 17:49:21 -0600
Update Date2015-09-14 11:20:00 -0600
Secondary Accession Numbers
  • ECMDB24106
Identification
Name:PE(15:0/15:0)
DescriptionPE(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:
ValueSource
Phophatidylethanolamine(30:0)HMDB
GPEtn(30:0)HMDB
Phophatidylethanolamine(15:0/15:0)HMDB
GPEtn(15:0/15:0)HMDB
PE(30:0)HMDB
1,2-Dipentadecanoyl-rac-glycero-3-phosphoethanolamineHMDB
PE(15:0/15:0)Lipid Annotator
Chemical Formula:C35H70NO8P
Weight:Average: 663.906
Monoisotopic: 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
Description 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoethanolamines
Direct ParentPhosphatidylethanolamines
Alternative Parents
Substituents
  • Diacylglycero-3-phosphoethanolamine
  • Phosphoethanolamine
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Primary amine
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00014 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count37ChemAxon
Refractivity181.8 m³·mol⁻¹ChemAxon
Polarizability81.18 ųChemAxon
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)
SMPDB Pathways:
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/15:0cyclo/18:1(9Z))PW001064 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/15:0cyclo/19:0cycv8c)PW001065 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/18:1(9Z)/15:0cyclo)PW001082 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(18:1(9Z)/15:0cyclo/14:0/15:0cyclo))PW001507 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(18:1(9Z)/15:0cyclo/17:0cycw7c/15:0cyclo))PW001527 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(18:1(9Z)/15:0cyclo/18:1(9Z)/15:0cyclo))PW001531 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(18:1(9Z)/15:0cyclo/19:0cycv8c/15:0cyclo))PW001577 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/16:1(9Z)/16:1(9Z))PW001068 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/18:1(9Z)/18:1(9Z))PW001085 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/19:0cycv8c/15:0cyclo)PW001088 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/15:0cyclo/16:1(9Z))PW001120 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/16:1(9Z)/15:0cyclo)PW001127 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/18:1(9Z)/15:0cyclo/18:1(9Z))PW001163 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/18:1(9Z)/18:1(9Z)/15:0cyclo)PW001173 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/14:0/15:0cyclo)PW001431 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/15:0cyclo/14:0) )PW001724 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/15:0cyclo/17:0cycw7c)PW001440 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/15:0cyclo/18:1(9Z))PW001441 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/16:1(9Z)/15:0cyclo)PW001451 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/18:1(9Z)/15:0cyclo)PW001460 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0010009000-bf29f526b3dc0d75633cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0010009000-bf29f526b3dc0d75633cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ox-0390306000-fd0bac05e999301c30aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000019000-3f586d70d000f4c90456View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0229-0010397000-b713a42cf9979cdc673aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0010393000-52febe36836d24fa12c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000019000-27a6d8e9e665f36a6b5dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000019000-9ea22d3f36be46f12634View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0100119000-650225973346e61e9fe9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000019000-c3fe7ec191a9b8064e7bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0229-0010397000-921c36e50d223c4dc0caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0010393000-c16f7bf68f2bba11abd4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0010009000-8e6a6ac250ece931a464View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0010009000-8e6a6ac250ece931a464View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ox-0390306000-a2e8b4c198b5caa82b49View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
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 IDHMDB0008889
Pubchem Compound ID9546807
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
Uniprot ID:
P0A8K1
Molecular weight:
35934
Reactions
Phosphatidyl-L-serine = phosphatidylethanolamine + CO(2).
General function:
cardiolipin biosynthetic process
Specific function:
Catalyzes the synthesis of cardiolipin (CL) (diphosphatidylglycerol) from phosphatidylglycerol (PG) and phosphatidylethanolamine (PE).
Gene Name:
clsC
Uniprot ID:
P75919
Molecular weight:
53665
Reactions
Phosphatidylglycerol + phosphatidylethanolamine = diphosphatidylglycerol + ethanolamine