PE(18:1(9Z)/14:0) (ECMDB24122) (M2MDB006239)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (2)
Record Information
Version2.0
Creation Date2015-09-08 17:49:29 -0600
Update Date2015-09-14 11:20:00 -0600
Secondary Accession Numbers
  • ECMDB24122
Identification
Name:PE(18:1(9Z)/14:0)
DescriptionPE(18:1(9Z)/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(9Z)/14:0), in particular, consists of one 9Z-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
MOLSDFPDBSMILESInChI
Synonyms:
ValueSource
1-(9Z)-Octadecenoyl-2-tetradecanoyl-sn-glycero-3-phosphoethanolamineChEBI
1-(9Z)-Octadecenoyl-2-tetradecanoyl-sn-glycero-3-phosphoethanolamine zwitterionChEBI
GPEtn(18:1/14:0)HMDB
Phophatidylethanolamine(18:1/14:0)HMDB
PE(18:1/14:0)HMDB
1-Oleoyl-2-myristoyl-sn-glycero-3-phosphoethanolamineHMDB
GPEtn(32:1)HMDB
Phophatidylethanolamine(32:1)HMDB
1-(9Z-Octadecenoyl)-2-tetradecanoyl-sn-glycero-3-phosphoethanolamineHMDB
PE(32:1)HMDB
PE(18:1(9Z)/14:0)Lipid Annotator
Chemical Formula:C37H72NO8P
Weight:Average: 689.9432
Monoisotopic: 689.499554797
InChI Key:MFWTZMQSTYTELL-XHYHITGYSA-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/h16-17,35H,3-15,18-34,38H2,1-2H3,(H,41,42)/b17-16-/t35-/m1/s1
CAS number:Not Available
IUPAC Name:(2-aminoethoxy)[(2R)-3-[(9Z)-octadec-9-enoyloxy]-2-(tetradecanoyloxy)propoxy]phosphinic acid
Traditional IUPAC Name:2-aminoethoxy((2R)-3-[(9Z)-octadec-9-enoyloxy]-2-(tetradecanoyloxy)propoxy)phosphinic acid
SMILES:[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(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 Descriptors
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility9.9e-05 g/LALOGPS
logP8.01ALOGPS
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
Polarizability83.66 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
PS(18:1(9Z)/14:0) + Hydrogen ion > PE(18:1(9Z)/14:0) + Carbon dioxide
PG(19:iso/19:0cycv8c) + PE(18:1(9Z)/14:0) > Ethanolamine + CL(18:1(9Z)/14:0/19:0cycv8c/19:0cycv8c)
PE(18:1(9Z)/14:0) + PG(14:0/14:0) > Ethanolamine + CL(18:1(9Z)/14:0/14:0/14:0)
PE(18:1(9Z)/14:0) + PG(18:1(9Z)/18:1(9Z)) > Ethanolamine + CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/14:0)
PE(18:1(9Z)/14:0) + PG(18:1(9Z)/16:0) > Ethanolamine + CL(18:1(9Z)/16:0/18:1(9Z)/14:0)
PE(18:1(9Z)/14:0) + PG(18:1(9Z)/16:1(9Z)) > Ethanolamine + CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/14:0)
SMPDB Pathways:
phospholipid biosynthesis (CL(18:1(9Z)/14:0/14:0/14:0))PW001493 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(18:1(9Z)/14:0/19:0cycv8c/19:0cycv8c) 2)PW001781 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(18:1(9Z)/16:0/18:1(9Z)/14:0))PW001587 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/14:0))PW001620 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/14:0))PW001686 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_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0030009000-a9e907e9bfd07ce2135fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0030009000-a9e907e9bfd07ce2135fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-005i-0190303000-cc54394b3ca262da6029View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000019000-a15ebcb20c9e09cf37dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0005-0011697000-2884cd6144c3bb1aec5cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0011693000-e15f22a4f276d8bbed83View 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, 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
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
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 ID78814
HMDB IDHMDB0009052
Pubchem Compound ID52924900
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Phosphatidylserine decarboxylase proenzyme
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).
Protein Details
2. 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