Showing metabocard for PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (BMDB0009472)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-10-03 17:43:34 UTC
Update Date2020-05-21 16:26:47 UTC
BMDB IDBMDB0009472
Secondary Accession Numbers
  • BMDB09472
Metabolite Identification
Common NamePE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))
DescriptionPE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)), also known as GPEtn(20:5/22:5) or pe(20:5(5z,8z,11z,14z,17z)/22:5(4z,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. PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)) is possibly soluble (in water) and a very strong basic compound (based on its pKa). PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)) participates in a number of enzymatic reactions, within cattle. In particular, PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)) can be biosynthesized from PS(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)); which is mediated by the enzyme phosphatidylserine decarboxylase. Furthermore, Cytidine monophosphate and PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)) can be biosynthesized from CDP-ethanolamine and DG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Furthermore, Cytidine monophosphate and PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)) can be biosynthesized from CDP-ethanolamine and DG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Finally, PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)) can be biosynthesized from PS(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)) through its interaction with the enzyme phosphatidylserine decarboxylase. In cattle, PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)) pathway and phosphatidylcholine biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Eicosapentaenoyl-2-osbondoyl-sn-glycero-3-phosphoethanolamineHMDB
GPEtn(20:5/22:5)HMDB
Phophatidylethanolamine(20:5/22:5)HMDB
PE(42:10)HMDB
PE(20:5/22:5)HMDB
Phophatidylethanolamine(42:10)HMDB
1-(5Z,8Z,11Z,14Z,17Z-Eicosapentaenoyl)-2-(4Z,7Z,10Z,13Z,16Z-docosapentaenoyl)-sn-glycero-3-phosphoethanolamineHMDB
GPEtn(42:10)HMDB
PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))Lipid Annotator
Chemical FormulaC47H74NO8P
Average Molecular Weight812.0661
Monoisotopic Molecular Weight811.515204861
IUPAC Name(2-aminoethoxy)[(2R)-2-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]-3-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propoxy]phosphinic acid
Traditional NamePPP
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)(COP(O)(=O)OCCN)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C47H74NO8P/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/h6,8,11-14,17-20,22,24-25,27-28,30-31,33-34,36,45H,3-5,7,9-10,15-16,21,23,26,29,32,35,37-44,48H2,1-2H3,(H,51,52)/b8-6-,13-11-,14-12-,19-17-,20-18-,24-22-,27-25-,30-28-,33-31-,36-34-/t45-/m1/s1
InChI KeyIOWGRRHLDCONTO-UPNCUQEWSA-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
logP8.07ALOGPS
logP11.28ChemAxon
logS-6.9ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area134.38 ŲChemAxon
Rotatable Bond Count39ChemAxon
Refractivity248.18 m³·mol⁻¹ChemAxon
Polarizability92.94 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, Negativesplash10-03di-0003000090-9df576106086c35cc8b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0003000090-9df576106086c35cc8b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0w6r-0109110030-7f132a104e2558e505a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000001190-a925c6378f75248a3ec0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0229-0003149160-7f9678dd809ada818394View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0003149110-6803407679ca11e3c669View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000001090-7f85ba2914c3b6529cc0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001l-0000002290-89ba690c21ca931b3663View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0100301910-038d215b54c778a7f592View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0003000090-ae8d9b86246fc444859fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0003000090-ae8d9b86246fc444859fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0w6r-0109110030-91b1de86b08c3574eaedView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000001190-267b579aaa6d8a56a821View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0229-0003149160-261c7674923159e5f3c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0003149110-7701353f3bab289e9f33View 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 IDHMDB0009472
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 Compound53479836
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(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) → Cytidine monophosphate + PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))details