Showing metabocard for PE(20:1(11Z)/22:2(13Z,16Z)) (BMDB0009272)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-10-03 17:39:13 UTC
Update Date2020-05-21 16:26:40 UTC
BMDB IDBMDB0009272
Secondary Accession Numbers
  • BMDB09272
Metabolite Identification
Common NamePE(20:1(11Z)/22:2(13Z,16Z))
DescriptionPE(20:1(11Z)/22:2(13Z,16Z)), also known as GPEtn(42:3) or GPEtn(20:1/22:2), 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. Thus, PE(20:1(11Z)/22:2(13Z,16Z)) is considered to be a glycerophosphoethanolamine lipid molecule. PE(20:1(11Z)/22:2(13Z,16Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PE(20:1(11Z)/22:2(13Z,16Z)) participates in a number of enzymatic reactions, within cattle. In particular, PE(20:1(11Z)/22:2(13Z,16Z)) can be biosynthesized from PS(20:1(11Z)/22:2(13Z,16Z)); which is catalyzed by the enzyme phosphatidylserine decarboxylase. Furthermore, Cytidine monophosphate and PE(20:1(11Z)/22:2(13Z,16Z)) can be biosynthesized from CDP-ethanolamine and DG(20:1(11Z)/22:2(13Z,16Z)/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Furthermore, Cytidine monophosphate and PE(20:1(11Z)/22:2(13Z,16Z)) can be biosynthesized from CDP-ethanolamine and DG(20:1(11Z)/22:2(13Z,16Z)/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Finally, PE(20:1(11Z)/22:2(13Z,16Z)) can be biosynthesized from PS(20:1(11Z)/22:2(13Z,16Z)); which is catalyzed by the enzyme phosphatidylserine decarboxylase. In cattle, PE(20:1(11Z)/22:2(13Z,16Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(20:1(11Z)/22:2(13Z,16Z)) pathway and phosphatidylcholine biosynthesis PC(20:1(11Z)/22:2(13Z,16Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
GPEtn(42:3)HMDB
1-Eicosenoyl-2-docosadienoyl-sn-glycero-3-phosphoethanolamineHMDB
PE(42:3)HMDB
GPEtn(20:1/22:2)HMDB
PE(20:1/22:2)HMDB
Phophatidylethanolamine(42:3)HMDB
1-(11-Eicosenoyl)-2-(13Z,16Z-docosadienoyl)-sn-glycero-3-phosphoethanolamineHMDB
Phophatidylethanolamine(20:1/22:2)HMDB
PE(20:1(11Z)/22:2(13Z,16Z))Lipid Annotator
Chemical FormulaC47H88NO8P
Average Molecular Weight826.1773
Monoisotopic Molecular Weight825.624755309
IUPAC Name(2-aminoethoxy)[(2R)-2-[(13Z,16Z)-docosa-13,16-dienoyloxy]-3-[(11Z)-icos-11-enoyloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-2-[(13Z,16Z)-docosa-13,16-dienoyloxy]-3-[(11Z)-icos-11-enoyloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCC\C=C/CCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C47H88NO8P/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-36-38-40-47(50)56-45(44-55-57(51,52)54-42-41-48)43-53-46(49)39-37-35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h11,13,17-20,45H,3-10,12,14-16,21-44,48H2,1-2H3,(H,51,52)/b13-11-,19-17-,20-18-/t45-/m1/s1
InChI KeyXOOQPCRWQRXZSU-RLWNNFTMSA-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
logP9.6ALOGPS
logP13.81ChemAxon
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 Count46ChemAxon
Refractivity240.36 m³·mol⁻¹ChemAxon
Polarizability102.14 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0003000090-8a9d46669021f017a949View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0003000090-8a9d46669021f017a949View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abr-0109020030-99f8b2b2e7c62f9a8ba3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000001090-91c3f888e5ff27cb4cd6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002r-0003149070-9f107d14bd1bbae310a0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0003149030-502ec5904fef99f36073View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000000190-1355bc21999067439122View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052b-0000000190-726bdf6f7558756df70aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0100200190-bc0901b1ea37d72cd0bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000001090-75946b7ca0320ffe853fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002r-0003149070-867ce47b3822eb27edccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0003149030-8cafb3a0f1e27c41c5d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0003000090-b0cb1b3f776767894799View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0003000090-b0cb1b3f776767894799View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abr-0109020030-97ea8dd577fb6ab6ff11View 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 IDHMDB0009272
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 Compound52924569
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Ethanolaminephosphotransferase 1
General function:
Involved in ethanolaminephosphotransferase activity
Specific function:
Catalyzes phosphatidylethanolamine biosynthesis from CDP-ethanolamine. It thereby plays a central role in the formation and maintenance of vesicular membranes. Involved in the foramtion of phosphatidylethanolamine via 'Kennedy' pathway (By similarity).
Gene Name:
SELENOI
Uniprot ID:
Q17QM4
Molecular weight:
45214.0
Reactions
CDP-Ethanolamine + DG(20:1(11Z)/22:2(13Z,16Z)/0:0) → Cytidine monophosphate + PE(20:1(11Z)/22:2(13Z,16Z))details