Showing metabocard for PE(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)) (BMDB0009100)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-10-03 17:35:45 UTC
Update Date2020-05-21 16:26:33 UTC
BMDB IDBMDB0009100
Secondary Accession Numbers
  • BMDB09100
Metabolite Identification
Common NamePE(18:2(9Z,12Z)/20:3(5Z,8Z,11Z))
DescriptionPE(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)), also known as GPEtn(18:2/20:3) or pe(18:2(9z,12z)/20:3(5z,8z,11z)), 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(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)) is possibly soluble (in water) and a very strong basic compound (based on its pKa). PE(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)) participates in a number of enzymatic reactions, within cattle. In particular, PE(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)) can be biosynthesized from PS(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)) through the action of the enzyme phosphatidylserine decarboxylase. Furthermore, Cytidine monophosphate and PE(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)) can be biosynthesized from CDP-ethanolamine and DG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Furthermore, Cytidine monophosphate and PE(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)) can be biosynthesized from CDP-ethanolamine and DG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Finally, PE(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)) can be biosynthesized from PS(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)); which is catalyzed by the enzyme phosphatidylserine decarboxylase. In cattle, PE(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)) pathway and phosphatidylcholine biosynthesis PC(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
GPEtn(18:2/20:3)HMDB
Phophatidylethanolamine(18:2/20:3)HMDB
Phophatidylethanolamine(38:5)HMDB
PE(18:2/20:3)HMDB
1-Linoleoyl-2-meadoyl-sn-glycero-3-phosphoethanolamineHMDB
PE(38:5)HMDB
1-(9Z,12Z-Octadecadienoyl)-2-(5Z,8Z,11Z-eicosatrienoyl)-sn-glycero-3-phosphoethanolamineHMDB
GPEtn(38:5)HMDB
PE(18:2(9Z,12Z)/20:3(5Z,8Z,11Z))Lipid Annotator
Chemical FormulaC43H76NO8P
Average Molecular Weight766.0392
Monoisotopic Molecular Weight765.530854925
IUPAC Name(2-aminoethoxy)[(2R)-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)(COP(O)(=O)OCCN)OC(=O)CCC\C=C/C\C=C/C\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C43H76NO8P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-43(46)52-41(40-51-53(47,48)50-38-37-44)39-49-42(45)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h12,14,17-19,21-22,24,28,30,41H,3-11,13,15-16,20,23,25-27,29,31-40,44H2,1-2H3,(H,47,48)/b14-12-,19-17-,21-18-,24-22-,30-28-/t41-/m1/s1
InChI KeyIXWDETUUUCHRRC-JASSPJQVSA-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
logP8.82ALOGPS
logP11.31ChemAxon
logS-7ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area134.38 ŲChemAxon
Rotatable Bond Count40ChemAxon
Refractivity224.19 m³·mol⁻¹ChemAxon
Polarizability91.46 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, Negativesplash10-03di-0011000900-0fd2a4d2e83be8c0dff2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0011000900-0fd2a4d2e83be8c0dff2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bxr-0399410600-accd414fa67c4adf9e85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000001900-7ee1f9262bf4b52ebb58View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00or-0003419700-e161e2f5cd7420ce6d6dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0003419300-51b6f32097531323ab7eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000001900-9fe007eaf888ac746f47View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000j-0000001900-d99ae6e4c65266940edaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0100201900-5104655692a99661c0edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0011000900-f374d9be1a1c83139aa8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0011000900-f374d9be1a1c83139aa8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bxr-0399410600-46a2abe3667b373957a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000001900-05647fd5fc9d523027f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00or-0003419700-648b4d0c64e81470edc3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0003419300-0313c997610ecbe3fc2aView 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 IDHMDB0009100
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB026290
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53479662
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(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/0:0) → Cytidine monophosphate + PE(18:2(9Z,12Z)/20:3(5Z,8Z,11Z))details