Showing metabocard for PE(20:0/18:1(11Z)) (BMDB0009223)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:38:13 UTC
Update Date2020-05-11 19:38:06 UTC
BMDB IDBMDB0009223
Secondary Accession Numbers
  • BMDB09223
Metabolite Identification
Common NamePE(20:0/18:1(11Z))
DescriptionPE(20:0/18:1(11Z)) 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(20:0/18:1(11Z)), in particular, consists of one eicosanoyl chain to the C-1 atom, and one 11Z-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
Phophatidylethanolamine(38:1)HMDB
PE(38:1)HMDB
GPEtn(20:0/18:1)HMDB
Phophatidylethanolamine(20:0/18:1)HMDB
GPEtn(38:1)HMDB
1-Arachidonyl-2-vaccenoyl-sn-glycero-3-phosphoethanolamineHMDB
PE(20:0/18:1)HMDB
1-Eicosanoyl-2-(11Z-octadecenoyl)-sn-glycero-3-phosphoethanolamineHMDB
PE(20:0/18:1(11Z))Lipid Annotator
Chemical FormulaC43H84NO8P
Average Molecular Weight774.1027
Monoisotopic Molecular Weight773.593455181
IUPAC Name(2-aminoethoxy)[(2R)-3-(icosanoyloxy)-2-[(11Z)-octadec-11-enoyloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-3-(icosanoyloxy)-2-[(11Z)-octadec-11-enoyloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCC\C=C/CCCCCC
InChI Identifier
InChI=1S/C43H84NO8P/c1-3-5-7-9-11-13-15-17-19-20-22-23-25-27-29-31-33-35-42(45)49-39-41(40-51-53(47,48)50-38-37-44)52-43(46)36-34-32-30-28-26-24-21-18-16-14-12-10-8-6-4-2/h14,16,41H,3-13,15,17-40,44H2,1-2H3,(H,47,48)/b16-14-/t41-/m1/s1
InChI KeyXYHIPPZFNNOMQL-MITQYPHISA-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
logP9.16ALOGPS
logP12.76ChemAxon
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 Count44ChemAxon
Refractivity219.73 m³·mol⁻¹ChemAxon
Polarizability96.58 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, Negativesplash10-00di-0011000900-754f7e0d9653c3d67ca8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0011000900-754f7e0d9653c3d67ca8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03l0-0399410600-fbefcfbcc7c4a1fc5878View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000001900-aa6a5c403040a5d512f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0089-0003419700-1e0748aa8026eb7be7f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0003419300-bba8268e9ad8f8a9b8f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000001900-a07764cbc04c28d46e5fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000001900-36ca3d18a885334ba357View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0100201900-f0a1388265758fbcbf3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000001900-ec60a8ee25ef12c2f40aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0089-0003419700-424913a2a279316e4a14View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0003419300-47b9531bbd2d8f031572View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0011000900-f39525b1e90dfe056af8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0011000900-f39525b1e90dfe056af8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03l0-0399410600-5dfe65da65306828e277View 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 IDHMDB0009223
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB026413
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9546838
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available