Record Information
Version2.0
Creation Date2012-05-31 14:13:34 -0600
Update Date2015-09-14 11:19:22 -0600
Secondary Accession Numbers
  • ECMDB08957
Identification
Name:PE(16:1(9Z)/16:1(9Z))
DescriptionPE(16:1(9Z)/16:1(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 positions. PE(16:1(9Z)/16:1(9Z)), in particular, consists of two 9Z-hexadecenoyl 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:
  • 1,2-di(9Z-hexadecenoyl)-rac-glycero-3-phosphoethanolamine
  • 1,2-Dipalmitoleoyl-rac-glycero-3-phosphoethanolamine
  • 1-phosphatidylethanolamine
  • O-(1-β-acyl-2-acyl-sn-glycero-3-phospho)-ethanolamine
  • A 1-phosphatidylethanolamine
  • A phosphatidylethenolamine
  • An L-1-phosphotidylethanolamine
  • Glycerophosphoethanolamine
  • GPEtn(16:1/16:1)
  • GPEtn(16:1n7/16:1n7)
  • GPEtn(16:1w7/16:1w7)
  • GPEtn(32:2)
  • L-1-phosphotidylethanolamine
  • O-(1-β-acyl-2-acyl-sn-glycero-3-phospho)-ethanolamine
  • PE(16:1/16:1)
  • PE(16:1n7/16:1n7)
  • PE(16:1w7/16:1w7)
  • PE(32:2)
  • Phophatidylethanolamine(16:1/16:1)
  • Phophatidylethanolamine(16:1n7/16:1n7)
  • Phophatidylethanolamine(16:1w7/16:1w7)
  • Phophatidylethanolamine(32:2)
  • Phosphatidylethanolamine
  • Phosphatidylethanolamine (ecoli)
  • PtdEtn
Chemical Formula:C37H70NO8P
Weight:Average: 687.9274
Monoisotopic: 687.483904733
InChI Key:PGPMCWZMPPZJML-NAFNZUQFSA-N
InChI:InChI=1S/C37H70NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-36(39)43-33-35(34-45-47(41,42)44-32-31-38)46-37(40)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13-16,35H,3-12,17-34,38H2,1-2H3,(H,41,42)/b15-13-,16-14-/t35-/m1/s1
CAS number:Not Available
IUPAC Name:(2-aminoethoxy)[(2R)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propoxy]phosphinic acid
Traditional IUPAC Name:2-aminoethoxy((2R)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propoxy)phosphinic acid
SMILES:[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCC\C=C/CCCCCC
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:Solid
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.0001 g/LALOGPS
logP7.89ALOGPS
logP9.73ChemAxon
logS-6.8ALOGPS
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
Refractivity193.24 m³·mol⁻¹ChemAxon
Polarizability82.09 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
SMPDB Pathways:
phospholipid biosynthesis CL(14:0/16:1(9Z)/14:0/16:1(9Z))PW001039 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/14:0/16:1(9Z)/16:1(9Z))PW001214 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/16:0/16:1(9Z)/16:1(9Z))PW001265 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/16:1(9Z)/16:0/16:1(9Z))PW001297 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/16:0)PW001308 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/14:0/14:0/16:1(9Z))PW001416 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/14:0/16:1(9Z)/14:0)PW001419 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/16:0)PW001486 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/14:0/14:0)PW001510 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0010009000-9467665e0186731a29a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0010009000-9467665e0186731a29a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-0390306000-8d97c6f6993df945bdd5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000019000-7de5e69af9b79891360eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000b-0001397000-fa7705935123e40e14ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0001393000-f9f1155e5ab5c1a08747View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000010900-d60ec87cde7d1e3d1bf5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03xr-0000022900-5d7005bec5982bccbceeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0100119100-5bfce3ea4c2b943f20faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0010009000-2985386274ae208b2fe2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0010009000-2985386274ae208b2fe2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-0390306000-fe45e046f9b9e7f53f8cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000019000-8c491c4aae9d3cb0e6dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000b-0001397000-4e8f38ec1ebb24c7f11bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0001393000-89b7c4d5ec9939688f97View 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 ID138145
HMDB IDHMDB08957
Pubchem Compound ID9546730
Kegg IDC00350
ChemSpider ID7825759
WikipediaLecithin
BioCyc IDL-1-PHOSPHATIDYL-ETHANOLAMINE
EcoCyc IDL-1-PHOSPHATIDYL-ETHANOLAMINE

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:
Involved in transferase activity, transferring acyl groups
Specific function:
Plays a role in lysophospholipid acylation. Transfers fatty acids to the 1-position via an enzyme-bound acyl-ACP intermediate in the presence of ATP and magnesium. Its physiological function is to regenerate phosphatidylethanolamine from 2-acyl-glycero-3-phosphoethanolamine (2-acyl-GPE) formed by transacylation reactions or degradation by phospholipase A1
Gene Name:
aas
Uniprot ID:
P31119
Molecular weight:
80699
Reactions
Acyl-[acyl-carrier-protein] + O-(2-acyl-sn-glycero-3-phospho)ethanolamine = [acyl-carrier-protein] + O-(1-beta-acyl-2-acyl-sn-glycero-3-phospho)ethanolamine.
ATP + an acid + [acyl-carrier-protein] = AMP + diphosphate + acyl-[acyl-carrier-protein].
General function:
Not Available
Specific function:
Not known; overproduction leads to camphor resistance and chromosome condensation
Gene Name:
crcA
Uniprot ID:
P37001
Molecular weight:
21770
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

Transporters

General function:
Involved in phospholipid transporter activity
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:
mlaB
Uniprot ID:
P64602
Molecular weight:
10680
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:
mlaD
Uniprot ID:
P64604
Molecular weight:
19576
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
Uniprot ID:
P64606
Molecular weight:
27863