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PE(16:0/14:1(9Z)) (M2MDB006227)

Record Information
Version2.0
Creation Date2015-09-08 17:49:23 -0600
Update Date2015-09-14 11:20:00 -0600
Secondary Accession Numbers
  • ECMDB24110
Identification
Name:PE(16:0/14:1(9Z))
DescriptionPE(16:0/14:1(9Z)) 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(16:0/14:1(9Z)), in particular, consists of one hexadecanoyl chain to the C-1 atom, and one 9Z-tetradecenoyl 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
MOLSDFPDBSMILESInChI
Synonyms:
ValueSource
Phophatidylethanolamine(16:0/14:1)HMDB
GPEtn(30:1)HMDB
PE(16:0/14:1)HMDB
Phophatidylethanolamine(30:1)HMDB
PE(30:1)HMDB
GPEtn(16:0/14:1)HMDB
1-Hexadecanoyl-2-(9Z-tetradecenoyl)-sn-glycero-3-phosphoethanolamineHMDB
1-Palmitoyl-2-myristoleoyl-sn-glycero-3-phosphoethanolamineHMDB
PE(16:0/14:1(9Z))Lipid Annotator
Chemical Formula:C35H68NO8P
Weight:Average: 661.8901
Monoisotopic: 661.468254669
InChI Key:NSRAJHJDVZNWFG-ALMVXPMNSA-N
InChI:InChI=1S/C35H68NO8P/c1-3-5-7-9-11-13-15-16-18-19-21-23-25-27-34(37)41-31-33(32-43-45(39,40)42-30-29-36)44-35(38)28-26-24-22-20-17-14-12-10-8-6-4-2/h10,12,33H,3-9,11,13-32,36H2,1-2H3,(H,39,40)/b12-10-/t33-/m1/s1
CAS number:Not Available
IUPAC Name:(2-aminoethoxy)[(2R)-3-(hexadecanoyloxy)-2-[(9Z)-tetradec-9-enoyloxy]propoxy]phosphinic acid
Traditional IUPAC Name:2-aminoethoxy((2R)-3-(hexadecanoyloxy)-2-[(9Z)-tetradec-9-enoyloxy]propoxy)phosphinic acid
SMILES:[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCC\C=C/CCCC
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
logP7.49ALOGPS
logP9.2ChemAxon
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 Count36ChemAxon
Refractivity182.92 m³·mol⁻¹ChemAxon
Polarizability79.5 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
PE(16:0/14:1(9Z)) + PG(16:0/16:0) > Ethanolamine + CL(16:0/16:1(9Z)/16:0/14:0)
SMPDB Pathways:
phospholipid biosynthesis CL(16:0/16:1(9Z)/16:0/14:0)PW001296 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 (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0030009000-8d546e170bd7a2b2deadView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0030009000-8d546e170bd7a2b2deadView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0r4i-0190303000-1fbb58132a75fff2f9d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000019000-fbd23580b5f8c70a170eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0229-0011697000-1061c71bff9052fe2849View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0011693000-6b3bcfdb4bd4a8a1ce5eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000019000-1cd30130f4f479dca1acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001l-0000019000-4423687200d2ef3d34d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0101119000-b371277a3eb57412b862View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0030009000-5b69cd33db7c3c42a5e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0030009000-5b69cd33db7c3c42a5e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0r4i-0190303000-5196cc28466aa465e278View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000019000-79e77b93d9865cb2cb9dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0229-0011697000-eb3576269855a7abc9dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0011693000-76a6e6138660a0ad9395View 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 IDHMDB0008921
Pubchem Compound ID52924209
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Cardiolipin synthase C
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