Showing metabocard for PE(20:2(11Z,14Z)/20:0) (BMDB0009295)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:39:40 UTC
Update Date2020-05-11 19:39:06 UTC
BMDB IDBMDB0009295
Secondary Accession Numbers
  • BMDB09295
Metabolite Identification
Common NamePE(20:2(11Z,14Z)/20:0)
DescriptionPE(20:2(11Z,14Z)/20:0) 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(20:2(11Z,14Z)/20:0), in particular, consists of one 11Z,14Z-eicosadienoyl chain to the C-1 atom, and one eicosanoyl 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-Eicosadienoyl-2-arachidonyl-sn-glycero-3-phosphoethanolamineHMDB
GPEtn(20:2/20:0)HMDB
Phophatidylethanolamine(40:2)HMDB
GPEtn(40:2)HMDB
PE(20:2/20:0)HMDB
Phophatidylethanolamine(20:2/20:0)HMDB
1-(11Z,14Z-Eicosadienoyl)-2-eicosanoyl-sn-glycero-3-phosphoethanolamineHMDB
PE(40:2)HMDB
PE(20:2(11Z,14Z)/20:0)Lipid Annotator
Chemical FormulaC45H86NO8P
Average Molecular Weight800.14
Monoisotopic Molecular Weight799.609105245
IUPAC Name(2-aminoethoxy)[(2R)-3-[(11Z,14Z)-icosa-11,14-dienoyloxy]-2-(icosanoyloxy)propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-3-[(11Z,14Z)-icosa-11,14-dienoyloxy]-2-(icosanoyloxy)propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCC\C=C/C\C=C/CCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C45H86NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-44(47)51-41-43(42-53-55(49,50)52-40-39-46)54-45(48)38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h11,13,17,19,43H,3-10,12,14-16,18,20-42,46H2,1-2H3,(H,49,50)/b13-11-,19-17-/t43-/m1/s1
InChI KeyLZGKJVBQJZESKW-MTFJKWJPSA-N
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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP9.44ALOGPS
logP13.28ChemAxon
logS-7.2ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area134.38 ŲChemAxon
Rotatable Bond Count45ChemAxon
Refractivity230.05 m³·mol⁻¹ChemAxon
Polarizability99.7 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0003000900-42ab812c54dcec726256View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0003000900-42ab812c54dcec726256View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bta-0109110300-c47301bceca8a32f4718View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000001190-434befa9b460fec0a1d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pb9-0003339160-1ba1e90a9d8d952e8904View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0003339110-9932e1b38c3808f73427View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000001090-51bfd56d984eba5a77edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000002290-dcdd17417c746e23e7aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0100301910-7a0abf7c60a9c4fd2424View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000001190-747ff52061625a754b28View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pb9-0003339160-b3bd4516cd36fe8b5849View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0003339110-655ec7627cbe44c718e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0003000900-c3d64e69aea5252b0e6bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0003000900-c3d64e69aea5252b0e6bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bta-0109110300-957d84f4bc81c097babaView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Brain
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0009295
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52924591
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available