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PE(16:0/18:1(9Z)) (M2MDB006230)

Record Information
Version2.0
Creation Date2015-09-08 17:49:26 -0600
Update Date2015-09-14 11:20:00 -0600
Secondary Accession Numbers
  • ECMDB24113
Identification
Name:PE(16:0/18:1(9Z))
DescriptionPE(16:0/18:1(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(16:0/18:1(9Z)), in particular, consists of one hexadecanoyl chain to the C-1 atom, and one 9Z-octadecenoyl 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-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamineChEBI
1-Hexadecanoyl-2-oleoyl-sn-glycero-3-phosphoethanolamine zwitterionChEBI
1-Palmitoyl-2-oleoyl-gpeChEBI
1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphoethanolamine zwitterionChEBI
GPE(16:0/18:1(9Z))ChEBI
GPE(16:0/18:1)ChEBI
GPE(34:1)ChEBI
1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphoethanolamineHMDB
Phophatidylethanolamine(16:0/18:1)HMDB
PE(34:1)HMDB
PE(16:0/18:1)HMDB
GPEtn(34:1)HMDB
Phophatidylethanolamine(34:1)HMDB
GPEtn(16:0/18:1)HMDB
1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphorylethanolamineHMDB
1-Palmitoyl-2-oleoyl-sn-glycero-phosphatidylethanolamineHMDB
1-Palmitoyl-2-oleoyl-sn-glyceryl-3-phosphorylethanolamineHMDB
1-Palmitoyl-2-oleoylcephalinHMDB
1-Palmitoyl-2-oleoylphosphatidylethanolamineHMDB
2-Oleoyl-1-palmitoyl-sn-glycero-3-phosphatidylethanolamineHMDB
GPE(16:0/18:1n9)HMDB
GPE(16:0/18:1W9)HMDB
GPEtn(16:0/18:1(9Z))HMDB
GPEtn(16:0/18:1n9)HMDB
GPEtn(16:0/18:1W9)HMDB
L-alpha-1-Palmitoyl-2-oleoylglycerophosphoethanolamineHMDB
L-Α-1-palmitoyl-2-oleoylglycerophosphoethanolamineHMDB
PE(16:0/18:1N9)HMDB
PE(16:0/18:1W9)HMDB
POPEHMDB
Phosphatidylethanolamine (16:0/18:1)HMDB
Phosphatidylethanolamine(16:0/18:1(9Z))HMDB
Phosphatidylethanolamine(16:0/18:1)HMDB
Phosphatidylethanolamine(16:0/18:1n9)HMDB
Phosphatidylethanolamine(16:0/18:1W9)HMDB
Phosphatidylethanolamine(34:1)HMDB
Alpha'-palmitoyl-beta-oleoylglycerophosphorylethanolamineHMDB
Α'-palmitoyl-β-oleoylglycerophosphorylethanolamineHMDB
Α’-palmitoyl-β-oleoylglycerophosphorylethanolamineHMDB
PE(16:0/18:1(9Z))Lipid Annotator
Chemical Formula:C39H76NO8P
Weight:Average: 717.9964
Monoisotopic: 717.530854925
InChI Key:FHQVHHIBKUMWTI-OTMQOFQLSA-N
InChI:InChI=1S/C39H76NO8P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-39(42)48-37(36-47-49(43,44)46-34-33-40)35-45-38(41)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h17-18,37H,3-16,19-36,40H2,1-2H3,(H,43,44)/b18-17-/t37-/m1/s1
CAS number:Not Available
IUPAC Name:(2-aminoethoxy)[(2R)-3-(hexadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphinic acid
Traditional IUPAC Name:2-aminoethoxy((2R)-3-(hexadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propoxy)phosphinic acid
SMILES:[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCC\C=C/CCCCCCCC
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 Solubility6.9e-05 g/LALOGPS
logP8.44ALOGPS
logP10.98ChemAxon
logS-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 Count40ChemAxon
Refractivity201.32 m³·mol⁻¹ChemAxon
Polarizability88.32 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
PS(16:0/18:1(9Z)) + Hydrogen ion > PE(16:0/18:1(9Z)) + Carbon dioxide
PE(16:0/18:1(9Z)) + PG(14:0/14:0) > Ethanolamine + CL(16:0/14:0/18:1(9Z)/14:0)
PG(16:0/16:0) + PE(16:0/18:1(9Z)) > Ethanolamine + CL(16:0/16:0/16:0/18:1(9Z))
PG(16:0/16:0) + PE(16:0/18:1(9Z)) > CL(16:0/16:0/18:1(9Z)/16:0) + Ethanolamine
PG(16:1(9Z)/16:1(9Z)) + PE(16:0/18:1(9Z)) > Ethanolamine + CL(16:0/16:1(9Z)/16:1(9Z)/18:1(9Z))
PG(16:1(9Z)/16:1(9Z)) + PE(16:0/18:1(9Z)) > Ethanolamine + CL(16:0/16:1(9Z)/18:1(9Z)/16:1(9Z))
PG(14:0/14:0) + PE(16:0/18:1(9Z)) > CL(16:0/18:1(9Z)/14:0/14:0) + Ethanolamine
PG(16:1(9Z)/16:1(9Z)) + PE(16:0/18:1(9Z)) > CL(16:0/18:1(9Z)/16:1(9Z)/16:1(9Z)) + Ethanolamine
PG(18:1(9Z)/18:1(9Z)) + PE(16:0/18:1(9Z)) > Ethanolamine + CL(16:0/18:1(9Z)/18:1(9Z)/18:1(9Z))
PG(16:1(9Z)/16:1(9Z)) + PE(16:0/18:1(9Z)) > Ethanolamine + CL(16:1(9Z)/16:0/16:1(9Z)/18:1(9Z))
PG(16:1(9Z)/16:1(9Z)) + PE(16:0/18:1(9Z)) > CL(16:1(9Z)/16:0/18:1(9Z)/16:1(9Z)) + Ethanolamine
PG(16:1(9Z)/16:1(9Z)) + PE(16:0/18:1(9Z)) > CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/16:0) + Ethanolamine
SMPDB Pathways:
phospholipid biosynthesis CL(16:0/14:0/18:1(9Z)/14:0)PW001216 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/16:0/16:0/18:1(9Z))PW001258 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/16:0/18:1(9Z)/16:0)PW001280 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:1(9Z))PW001313 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/16:1(9Z))PW001329 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/18:1(9Z)/14:0/14:0)PW001355 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/16:1(9Z))PW001362 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:1(9Z))PW001371 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:1(9Z))PW001489 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/16:1(9Z))PW001503 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/16:0)PW001546 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_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - QqQ 1V, negativesplash10-001i-0090000100-2e9d9a8d8feca579aacaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - IT 40V, negativesplash10-05o0-0090300300-5dca79ab504547b01f82View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 43V, positivesplash10-0159-0001493600-5907ebc5c0953d384058View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 2V, positivesplash10-014i-0000010900-c9437cd99b6b171adfdcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-014i-0000030900-bd57a871db71d1bf70dfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 6V, positivesplash10-016r-0001070900-d2f866f61d4f92564a28View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 8V, positivesplash10-00or-0001090600-dd0bbf82cb7b06430dfcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-004i-0001090300-a607c44099ff83629c56View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 12V, positivesplash10-004i-0001090300-82b4814349c972c80cdeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 16V, positivesplash10-004i-1002090100-497394a1af38d43c2314View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 18V, positivesplash10-004i-0002090000-5f6262b8cc3cf72935c6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-004i-2011090000-cd010912f5172b6da54fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 23V, positivesplash10-004i-3213090000-1548550e35e3d9c8fcf9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 27V, positivesplash10-004i-5032090000-9b380fedebc72ca568c7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - IT 30V, positivesplash10-004i-0000090200-c4efcd6150cb11f1fb9aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 20V, positivesplash10-016r-0000040900-a387fa9204d6a9e5d009View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 30V, positivesplash10-004i-0000090100-fb4b6d8a1afa5d49f1e0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 40V, positivesplash10-004i-0000090000-ad39b1973c677a1cdd07View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 50V, positivesplash10-004i-1110090000-4175c9cf5ace54980f84View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0030000900-dd1a62d29ee1a90ddd63View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0030000900-dd1a62d29ee1a90ddd63View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05o0-0190300300-262655b873a3fd0a874cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000010900-6f573d993dec08dd3c88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00or-0003690700-f71e3df43eaec8018c6fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0003690300-952c4e3ba35083fefda6View 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 ID73007
HMDB IDHMDB0008927
Pubchem Compound ID5283496
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