Showing metabocard for PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z)) (BMDB0009476)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-10-03 17:43:39 UTC
Update Date2020-05-21 16:26:47 UTC
BMDB IDBMDB0009476
Secondary Accession Numbers
  • BMDB09476
Metabolite Identification
Common NamePE(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))
DescriptionPE(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z)), also known as PE(44:6) or GPEtn(20:5/24:1), 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)/24:1(15Z)) is possibly soluble (in water) and a very strong basic compound (based on its pKa). PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z)) participates in a number of enzymatic reactions, within cattle. In particular, PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z)) can be biosynthesized from PS(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z)); which is mediated by the enzyme phosphatidylserine decarboxylase. Furthermore, Cytidine monophosphate and PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z)) can be biosynthesized from CDP-ethanolamine and DG(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z)/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Furthermore, Cytidine monophosphate and PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z)) can be biosynthesized from CDP-ethanolamine and DG(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z)/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Finally, PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z)) can be biosynthesized from PS(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z)); which is mediated by the enzyme phosphatidylserine decarboxylase. In cattle, PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z)) pathway and phosphatidylcholine biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
PE(44:6)HMDB
GPEtn(20:5/24:1)HMDB
GPEtn(44:6)HMDB
PE(20:5/24:1)HMDB
Phophatidylethanolamine(20:5/24:1)HMDB
1-Eicosapentaenoyl-2-nervonoyl-sn-glycero-3-phosphoethanolamineHMDB
Phophatidylethanolamine(44:6)HMDB
1-(5Z,8Z,11Z,14Z,17Z-Eicosapentaenoyl)-2-(15Z-tetracosanoyl)-sn-glycero-3-phosphoethanolamineHMDB
PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))Lipid Annotator
Chemical FormulaC49H86NO8P
Average Molecular Weight848.1828
Monoisotopic Molecular Weight847.609105245
IUPAC Name(2-aminoethoxy)[(2R)-3-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]-2-[(15Z)-tetracos-15-enoyloxy]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)CCCCCCCCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C49H86NO8P/c1-3-5-7-9-11-13-15-17-19-21-22-23-24-26-28-30-32-34-36-38-40-42-49(52)58-47(46-57-59(53,54)56-44-43-50)45-55-48(51)41-39-37-35-33-31-29-27-25-20-18-16-14-12-10-8-6-4-2/h6,8,12,14,17-20,27,29,33,35,47H,3-5,7,9-11,13,15-16,21-26,28,30-32,34,36-46,50H2,1-2H3,(H,53,54)/b8-6-,14-12-,19-17-,20-18-,29-27-,35-33-/t47-/m1/s1
InChI KeyJWOCZZMDIHXGFP-OIJZNSFSSA-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
logP9.55ALOGPS
logP13.61ChemAxon
logS-7.3ALOGPS
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
Polarizability102.11 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, Negativesplash10-0002-0003000090-26cb2c11510eab6fe9d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0003000090-26cb2c11510eab6fe9d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uxs-0109110030-5580eeb68abbd03d15fbView 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, Positivesplash10-0a4j-0001340970-316e86606d8c9e2f293fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0001340930-3b22e1b004b1dbb726adView 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, Positivesplash10-0a4j-0001340970-7efa77c8dbc3c6d578f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0001340930-515ca8aa7e6a2b382b6dView 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-0100110190-44665a2cc104726c8d94View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0003000090-7ecea0ab463a3d0bcbc3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0003000090-7ecea0ab463a3d0bcbc3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uxs-0109110030-dd5e7c63830d9c055152View 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 IDHMDB0009476
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 Compound53479838
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)/24:1(15Z)/0:0) → Cytidine monophosphate + PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))details