Showing metabocard for PE(20:1(11Z)/20:3(5Z,8Z,11Z)) (BMDB0009265)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-10-03 17:39:04 UTC
Update Date2020-05-21 16:26:40 UTC
BMDB IDBMDB0009265
Secondary Accession Numbers
  • BMDB09265
Metabolite Identification
Common NamePE(20:1(11Z)/20:3(5Z,8Z,11Z))
DescriptionPE(20:1(11Z)/20:3(5Z,8Z,11Z)), also known as PE(40:4) or GPEtn(20:1/20:3), 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(20:1(11Z)/20:3(5Z,8Z,11Z)) is possibly soluble (in water) and a very strong basic compound (based on its pKa). PE(20:1(11Z)/20:3(5Z,8Z,11Z)) participates in a number of enzymatic reactions, within cattle. In particular, PE(20:1(11Z)/20:3(5Z,8Z,11Z)) can be biosynthesized from PS(20:1(11Z)/20:3(5Z,8Z,11Z)); which is catalyzed by the enzyme phosphatidylserine decarboxylase. Furthermore, Cytidine monophosphate and PE(20:1(11Z)/20:3(5Z,8Z,11Z)) can be biosynthesized from CDP-ethanolamine and DG(20:1(11Z)/20:3(5Z,8Z,11Z)/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Furthermore, Cytidine monophosphate and PE(20:1(11Z)/20:3(5Z,8Z,11Z)) can be biosynthesized from CDP-ethanolamine and DG(20:1(11Z)/20:3(5Z,8Z,11Z)/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Finally, PE(20:1(11Z)/20:3(5Z,8Z,11Z)) can be biosynthesized from PS(20:1(11Z)/20:3(5Z,8Z,11Z)); which is mediated by the enzyme phosphatidylserine decarboxylase. In cattle, PE(20:1(11Z)/20:3(5Z,8Z,11Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(20:1(11Z)/20:3(5Z,8Z,11Z)) pathway and phosphatidylcholine biosynthesis PC(20:1(11Z)/20:3(5Z,8Z,11Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
PE(40:4)HMDB
GPEtn(20:1/20:3)HMDB
PE(20:1/20:3)HMDB
Phophatidylethanolamine(40:4)HMDB
Phophatidylethanolamine(20:1/20:3)HMDB
1-Eicosenoyl-2-meadoyl-sn-glycero-3-phosphoethanolamineHMDB
1-(11-Eicosenoyl)-2-(5Z,8Z,11Z-eicosatrienoyl)-sn-glycero-3-phosphoethanolamineHMDB
GPEtn(40:4)HMDB
PE(20:1(11Z)/20:3(5Z,8Z,11Z))Lipid Annotator
Chemical FormulaC45H82NO8P
Average Molecular Weight796.1082
Monoisotopic Molecular Weight795.577805117
IUPAC Name(2-aminoethoxy)[(2R)-3-[(11Z)-icos-11-enoyloxy]-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-3-[(11Z)-icos-11-enoyloxy]-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCC\C=C/CCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCC\C=C/C\C=C/C\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C45H82NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-44(47)51-41-43(42-53-55(49,50)52-40-39-46)54-45(48)38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h17-20,24,26,30,32,43H,3-16,21-23,25,27-29,31,33-42,46H2,1-2H3,(H,49,50)/b19-17-,20-18-,26-24-,32-30-/t43-/m1/s1
InChI KeyFEPPCXIJSFVQDL-IKEWFQJZSA-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
logP9.37ALOGPS
logP12.56ChemAxon
logS-7.1ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area134.38 ŲChemAxon
Rotatable Bond Count43ChemAxon
Refractivity232.28 m³·mol⁻¹ChemAxon
Polarizability97.17 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, Negativesplash10-0006-0003000900-63b15272f9d6cd532dd3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0003000900-63b15272f9d6cd532dd3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0109110300-f6469d91d74e4f6e7cebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000001900-e4c6e7b2865871b4c0cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-0003339700-74d86d1d36d4c7aec6dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0003339300-1e09d9a53b337b52a505View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0003000900-3a396c12cf93fe44ff2aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0003000900-3a396c12cf93fe44ff2aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0109110300-728b4aaae5eb4d93927bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000001900-82b1b3b32ab43ea49702View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-0003339700-6a3e5292bd5fba0c507fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0003339300-8a87b1c4404ff0ec5550View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000001090-7c25145fd7409b75812bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016r-0000002290-7dd7dedffbe696e1ba65View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0100301910-40324598c75cff0b9269View 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 IDHMDB0009265
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 Compound53479719
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(20:1(11Z)/20:3(5Z,8Z,11Z)/0:0) → Cytidine monophosphate + PE(20:1(11Z)/20:3(5Z,8Z,11Z))details