Record Information
Version2.0
Creation Date2012-05-31 14:13:40 -0600
Update Date2015-09-14 11:19:22 -0600
Secondary Accession Numbers
  • ECMDB09019
Identification
Name:PE(18:1(11Z)/14:0)
DescriptionPE(18:1(11Z)/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(18:1(11Z)/14:0), in particular, consists of one 11Z-octadecenoyl 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
Synonyms:
  • 1-(11Z-octadecenoyl)-2-tetradecanoyl-sn-glycero-3-phosphoethanolamine
  • 1-phosphatidylethanolamine
  • 1-Vaccenoyl-2-myristoyl-sn-glycero-3-phosphoethanolamine
  • O-(1-β-acyl-2-acyl-sn-glycero-3-phospho)-ethanolamine
  • A 1-phosphatidylethanolamine
  • A phosphatidylethenolamine
  • An L-1-phosphotidylethanolamine
  • Glycerophosphoethanolamine
  • GPEtn(18:1/14:0)
  • GPEtn(18:1n7/14:0)
  • GPEtn(18:1w7/14:0)
  • GPEtn(32:1)
  • L-1-phosphotidylethanolamine
  • O-(1-β-acyl-2-acyl-sn-glycero-3-phospho)-ethanolamine
  • PE(18:1/14:0)
  • PE(18:1n7/14:0)
  • PE(18:1w7/14:0)
  • PE(32:1)
  • Phophatidylethanolamine(18:1/14:0)
  • Phophatidylethanolamine(18:1n7/14:0)
  • Phophatidylethanolamine(18:1w7/14:0)
  • Phophatidylethanolamine(32:1)
  • Phosphatidylethanolamine
  • Phosphatidylethanolamine (ecoli)
  • PtdEtn
Chemical Formula:C37H72NO8P
Weight:Average: 689.9432
Monoisotopic: 689.499554797
InChI Key:ONLSYXWRWGUPKV-JUOLSMOWSA-N
InChI:InChI=1S/C37H72NO8P/c1-3-5-7-9-11-13-15-16-17-18-20-21-23-25-27-29-36(39)43-33-35(34-45-47(41,42)44-32-31-38)46-37(40)30-28-26-24-22-19-14-12-10-8-6-4-2/h13,15,35H,3-12,14,16-34,38H2,1-2H3,(H,41,42)/b15-13-/t35-/m1/s1
CAS number:Not Available
IUPAC Name:(2-aminoethoxy)[(2R)-3-[(11Z)-octadec-11-enoyloxy]-2-(tetradecanoyloxy)propoxy]phosphinic acid
Traditional IUPAC Name:2-aminoethoxy((2R)-3-[(11Z)-octadec-11-enoyloxy]-2-(tetradecanoyloxy)propoxy)phosphinic acid
SMILES:[H][C@@](COC(=O)CCCCCCCCC\C=C/CCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCC
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 DescriptorsNot Available
Physical Properties
State:Solid
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility9.9e-05 g/LALOGPS
logP7.99ALOGPS
logP10.09ChemAxon
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 Count38ChemAxon
Refractivity192.12 m³·mol⁻¹ChemAxon
Polarizability84.09 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(19:0/18:1(11Z)/14:0/14:0))PW001986 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 (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9140102000-24e4695b0eada7a78affView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9230001000-cfdb06ae4dd0bf7b6e6aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9142021000-133e67b43dbb5fc02128View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03gi-0190203000-49d602a08527211c4059View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01u3-4390101000-7294570b99c4f8f4ecfeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9220000000-7df03e29796babe99c08View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000010900-d71570caf7eecd1218c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000022900-87a2cd13fd62a0ed0a6fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0101119100-6e3906429c04a1a377c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0030009000-ed1ec79aac8617fccfdaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0030009000-ed1ec79aac8617fccfdaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-005i-0190303000-6dd7480aa09504760a1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000019000-97c11016ea748a8c68d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0005-0011697000-c8c712c46be915d12b75View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0011693000-e443eb3bcb9668a96fb9View 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 IDHMDB09019
Pubchem Compound ID53479618
Kegg IDC00350
ChemSpider ID24768492
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

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