PE(18:1(9Z)/16:0) (ECMDB24124) (M2MDB006241)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (2)
Record Information
Version2.0
Creation Date2015-09-08 17:49:30 -0600
Update Date2015-09-14 11:20:00 -0600
Secondary Accession Numbers
  • ECMDB24124
Identification
Name:PE(18:1(9Z)/16:0)
DescriptionPE(18:1(9Z)/16:0) 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)/16:0), in particular, consists of one 9Z-octadecenoyl chain to the C-1 atom, and one hexadecanoyl 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-hexadecanoyl-sn-glycero-3-phosphoethanolamine zwitterionChEBI
1-(9Z-Octadecenoyl)-2-hexadecanoyl-sn-glycero-3-phosphoethanolamineChEBI
2-Azaniumylethyl (2R)-3-[(9Z)-octadec-9-enoyloxy]-2-(palmitoyloxy)propyl phosphateChEBI
2-Azaniumylethyl (2R)-3-[(9Z)-octadec-9-enoyloxy]-2-(palmitoyloxy)propyl phosphoric acidGenerator
PE(34:1)HMDB
Phophatidylethanolamine(18:1/16:0)HMDB
1-Oleoyl-2-palmitoyl-sn-glycero-3-phosphoethanolamineHMDB
Phophatidylethanolamine(34:1)HMDB
PE(18:1/16:0)HMDB
GPEtn(18:1/16:0)HMDB
GPEtn(34:1)HMDB
PE(18:1(9Z)/16:0)Lipid Annotator
Chemical Formula:C39H76NO8P
Weight:Average: 717.9964
Monoisotopic: 717.530854925
InChI Key:DVXMEPWDARXHCX-OTMQOFQLSA-N
InChI:InChI=1S/C39H76NO8P/c1-3-5-7-9-11-13-15-17-18-20-21-23-25-27-29-31-38(41)45-35-37(36-47-49(43,44)46-34-33-40)48-39(42)32-30-28-26-24-22-19-16-14-12-10-8-6-4-2/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)-2-(hexadecanoyloxy)-3-[(9Z)-octadec-9-enoyloxy]propoxy]phosphinic acid
Traditional IUPAC Name:2-aminoethoxy((2R)-2-(hexadecanoyloxy)-3-[(9Z)-octadec-9-enoyloxy]propoxy)phosphinic acid
SMILES:[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCCCC
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
logP8.43ALOGPS
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
Polarizability87.86 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)/16:0) + Hydrogen ion > PE(18:1(9Z)/16:0) + Carbon dioxide
PG(16:0/19:iso) + PE(18:1(9Z)/16:0) > CL(18:1(9Z)/16:0/16:0/19:0cycv8c) + Ethanolamine
PG(16:0/14:0) + PE(18:1(9Z)/16:0) > Ethanolamine + CL(18:1(9Z)/16:0/16:0/14:0)
PG(16:0/17:0cycw7c) + PE(18:1(9Z)/16:0) > Ethanolamine + CL(18:1(9Z)/16:0/16:0/17:0cycw7c)
PE(18:1(9Z)/16:0) + PG(16:1(9Z)/18:1(9Z)) > Ethanolamine + CL(18:1(9Z)/16:0/16:1(9Z)/18:1(9Z))
SMPDB Pathways:
phospholipid biosynthesis (CL(18:1(9Z)/16:0/16:0/14:0))PW002011 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(18:1(9Z)/16:0/16:0/17:0cycw7c))PW002012 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(18:1(9Z)/16:0/16:0/19:0cycv8c) 2)PW001783 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(18:1(9Z)/16:0/16:1(9Z)/18:1(9Z)))PW002013 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_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0030000900-e2be313438f7b292fc76View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0030000900-e2be313438f7b292fc76View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05o0-0190300300-de84ed72de7818dd083fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000010900-4384bbfae935cffc95d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0007-0000022900-ad5dbee97cbecdd5b53aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0100319100-e6b2bcab57e92fa6966fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000010900-371a20b1ba3d80b384eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00or-0003690700-939d6395b3fec7521b7fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0003690300-53cb79d652bc5ebdf66eView in MoNA
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 ID78813
HMDB IDHMDB0009055
Pubchem Compound ID9546802
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