Showing metabocard for PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:0) (BMDB0009475)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-10-03 17:43:38 UTC
Update Date2020-05-21 16:26:47 UTC
BMDB IDBMDB0009475
Secondary Accession Numbers
  • BMDB09475
Metabolite Identification
Common NamePE(20:5(5Z,8Z,11Z,14Z,17Z)/24:0)
DescriptionPE(20:5(5Z,8Z,11Z,14Z,17Z)/24:0), also known as PE(44:5) or pe(20:5(5z,8z,11z,14z,17z)/24:0), 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)/24:0) is possibly soluble (in water) and a very strong basic compound (based on its pKa). PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:0) participates in a number of enzymatic reactions, within cattle. In particular, PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:0) can be biosynthesized from PS(20:5(5Z,8Z,11Z,14Z,17Z)/24:0); which is mediated by the enzyme phosphatidylserine decarboxylase. Furthermore, Cytidine monophosphate and PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:0) can be biosynthesized from CDP-ethanolamine and DG(20:5(5Z,8Z,11Z,14Z,17Z)/24:0/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Furthermore, Cytidine monophosphate and PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:0) can be biosynthesized from CDP-ethanolamine and DG(20:5(5Z,8Z,11Z,14Z,17Z)/24:0/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Finally, PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:0) can be biosynthesized from PS(20:5(5Z,8Z,11Z,14Z,17Z)/24:0); which is mediated by the enzyme phosphatidylserine decarboxylase. In cattle, PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:0) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(20:5(5Z,8Z,11Z,14Z,17Z)/24:0) pathway and phosphatidylcholine biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
PE(44:5)HMDB
Phophatidylethanolamine(20:5/24:0)HMDB
GPEtn(44:5)HMDB
PE(20:5/24:0)HMDB
1-Eicosapentaenoyl-2-lignoceroyl-sn-glycero-3-phosphoethanolamineHMDB
Phophatidylethanolamine(44:5)HMDB
1-(5Z,8Z,11Z,14Z,17Z-Eicosapentaenoyl)-2-tetracosanoyl-sn-glycero-3-phosphoethanolamineHMDB
GPEtn(20:5/24:0)HMDB
PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:0)Lipid Annotator
Chemical FormulaC49H88NO8P
Average Molecular Weight850.1987
Monoisotopic Molecular Weight849.624755309
IUPAC Name(2-aminoethoxy)[(2R)-3-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]-2-(tetracosanoyloxy)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)CCCCCCCCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C49H88NO8P/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/h6,8,12,14,18,20,27,29,33,35,47H,3-5,7,9-11,13,15-17,19,21-26,28,30-32,34,36-46,50H2,1-2H3,(H,53,54)/b8-6-,14-12-,20-18-,29-27-,35-33-/t47-/m1/s1
InChI KeyBNKVULSWPODLQA-TUPUMFGKSA-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
logP9.75ALOGPS
logP13.98ChemAxon
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
Refractivity251.8 m³·mol⁻¹ChemAxon
Polarizability103.91 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, Negativesplash10-0002-0003000090-642bd6b6fd4ee100bdc0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0003000090-642bd6b6fd4ee100bdc0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uxt-0109110030-c88dfe4f4abd2c1d34d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000190-a1efad39682cc4033b39View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pb9-0001340970-700641e507675931c9f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0001340930-e89c38bae585632d33b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000000190-f6dd591eb08b9b20154fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000000190-a14f3475a42c7480e3d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0100110190-d1bb8457fe954c06bf7fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000190-0ee06b3c256fa85d6d56View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pb9-0001340970-5dbf5913cb2d88024f85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0001340930-254cee58a3fa9353a292View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0003000090-a515b9c72e7901b7b153View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0003000090-a515b9c72e7901b7b153View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fr2-0109110030-4f6964d03acefdb92d9bView 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 IDHMDB0009475
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB026665
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53479837
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)/24:0/0:0) → Cytidine monophosphate + PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:0)details