Showing metabocard for PE(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)) (BMDB0009570)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-10-03 17:45:37 UTC
Update Date2020-05-21 16:26:48 UTC
BMDB IDBMDB0009570
Secondary Accession Numbers
  • BMDB09570
Metabolite Identification
Common NamePE(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))
DescriptionPE(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)), also known as GPEtn(44:6) or pe(22:2(13z,16z)/22:4(7z,10z,13z,16z)), 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(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)) is considered to be a glycerophosphoethanolamine lipid molecule. PE(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PE(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)) participates in a number of enzymatic reactions, within cattle. In particular, PE(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)) can be biosynthesized from PS(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)); which is catalyzed by the enzyme phosphatidylserine decarboxylase. Furthermore, Cytidine monophosphate and PE(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)) can be biosynthesized from CDP-ethanolamine and DG(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Furthermore, Cytidine monophosphate and PE(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)) can be biosynthesized from CDP-ethanolamine and DG(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Finally, PE(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)) can be biosynthesized from PS(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)) through its interaction with the enzyme phosphatidylserine decarboxylase. In cattle, PE(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)) pathway and phosphatidylcholine biosynthesis PC(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
GPEtn(44:6)HMDB
1-Docosadienoyl-2-adrenoyl-sn-glycero-3-phosphoethanolamineHMDB
PE(44:6)HMDB
Phophatidylethanolamine(22:2/22:4)HMDB
GPEtn(22:2/22:4)HMDB
Phophatidylethanolamine(44:6)HMDB
1-(13Z,16Z-Docosadienoyl)-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycero-3-phosphoethanolamineHMDB
PE(22:2/22:4)HMDB
PE(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))Lipid Annotator
Chemical FormulaC49H86NO8P
Average Molecular Weight848.1828
Monoisotopic Molecular Weight847.609105245
IUPAC Name(2-aminoethoxy)[(2R)-3-[(13Z,16Z)-docosa-13,16-dienoyloxy]-2-[(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoyloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-3-[(13Z,16Z)-docosa-13,16-dienoyloxy]-2-[(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoyloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCCC\C=C/C\C=C/CCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C49H86NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-39-41-48(51)55-45-47(46-57-59(53,54)56-44-43-50)58-49(52)42-40-38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h11-14,17-20,24,26,30,32,47H,3-10,15-16,21-23,25,27-29,31,33-46,50H2,1-2H3,(H,53,54)/b13-11-,14-12-,19-17-,20-18-,26-24-,32-30-/t47-/m1/s1
InChI KeyNNAMTGGOGLHJAZ-CHWHTWQNSA-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
logP9.47ALOGPS
logP13.61ChemAxon
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
Refractivity252.92 m³·mol⁻¹ChemAxon
Polarizability102.47 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, Negativesplash10-0002-0003000090-02fb0841d7f92f1c702eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0003000090-02fb0841d7f92f1c702eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001s-0109030030-b32b16007e98c76a0b5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000000190-21e530eaf5009fe9421aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a5a-0003060970-88a8abd24da9efc892a0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-0003060930-50aa25cb66f7616a2e9bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000000190-c945684e79f85b506c7dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fr-0000000190-5607e59b4d0900f2f414View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0100200190-17bc7021bccdad5f13b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0003000090-4a35bfac9a15367d6af7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0003000090-4a35bfac9a15367d6af7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001s-0109030030-317e6ca2081ef2f5f82aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000000190-fc70873a7b0e3203c96cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a5a-0003060970-b8040fddf7e31e14f269View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-0003060930-26941f54edce85ac22adView 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 IDHMDB0009570
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB026760
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52924801
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(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/0:0) → Cytidine monophosphate + PE(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))details