Showing metabocard for PE(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (BMDB0009572)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-10-03 17:45:40 UTC
Update Date2020-05-21 16:26:49 UTC
BMDB IDBMDB0009572
Secondary Accession Numbers
  • BMDB09572
Metabolite Identification
Common NamePE(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))
DescriptionPE(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)), also known as GPEtn(44:7) or PE(22:2/22:5), 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. PE(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) is possibly soluble (in water) and a very strong basic compound (based on its pKa). PE(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) participates in a number of enzymatic reactions, within cattle. In particular, PE(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) can be biosynthesized from PS(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) through the action of the enzyme phosphatidylserine decarboxylase. Furthermore, Cytidine monophosphate and PE(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) can be biosynthesized from CDP-ethanolamine and DG(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Furthermore, Cytidine monophosphate and PE(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) can be biosynthesized from CDP-ethanolamine and DG(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Finally, PE(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) can be biosynthesized from PS(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) through its interaction with the enzyme phosphatidylserine decarboxylase. In cattle, PE(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) pathway and phosphatidylcholine biosynthesis PC(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
GPEtn(44:7)HMDB
PE(22:2/22:5)HMDB
PE(44:7)HMDB
GPEtn(22:2/22:5)HMDB
Phophatidylethanolamine(22:2/22:5)HMDB
Phophatidylethanolamine(44:7)HMDB
1-Docosadienoyl-2-docosapentaenoyl-sn-glycero-3-phosphoethanolamineHMDB
1-(13Z,16Z-Docosadienoyl)-2-(7Z,10Z,13Z,16Z,19Z-docosapentaenoyl)-sn-glycero-3-phosphoethanolamineHMDB
PE(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))Lipid Annotator
Chemical FormulaC49H84NO8P
Average Molecular Weight846.1669
Monoisotopic Molecular Weight845.593455181
IUPAC Name(2-aminoethoxy)[(2R)-3-[(13Z,16Z)-docosa-13,16-dienoyloxy]-2-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-3-[(13Z,16Z)-docosa-13,16-dienoyloxy]-2-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]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/C\C=C/CC
InChI Identifier
InChI=1S/C49H84NO8P/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/h6,8,11-14,17-20,24,26,30,32,47H,3-5,7,9-10,15-16,21-23,25,27-29,31,33-46,50H2,1-2H3,(H,53,54)/b8-6-,13-11-,14-12-,19-17-,20-18-,26-24-,32-30-/t47-/m1/s1
InChI KeyLYDMBIIRDDVUSG-BKTJFRPDSA-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 DescriptorsNot Available
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
logP9.26ALOGPS
logP13.25ChemAxon
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
Refractivity254.03 m³·mol⁻¹ChemAxon
Polarizability100.89 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, Negativesplash10-0006-0003000090-583192ae5ce9849fdd0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0003000090-583192ae5ce9849fdd0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004u-0109030030-c6a9ac49f66713af0f0bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000000190-d5b0cf14ff8b4de06aa1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-0003060970-019d8d61415b50e10b02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0003060930-5896084b2725584cf291View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000000190-c5862192ca4cad37a31eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016r-0000000190-ec31fe29cb8e3c5d6b0eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0100200190-5c888f7d4a40955ddf75View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000000190-e8a022a818e1bdd264c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-0003060970-f0390170a8ffa0836716View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0003060930-a58f240431814e6addbeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0003000090-7d41b28ade470c18f78aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0003000090-7d41b28ade470c18f78aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004u-0109030030-ec2b461fd949d7edb796View 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 IDHMDB0009572
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 Compound53479890
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)/22:5(7Z,10Z,13Z,16Z,19Z)/0:0) → Cytidine monophosphate + PE(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))details