Showing metabocard for PE(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)) (BMDB0009165)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-10-03 17:37:03 UTC
Update Date2020-05-21 16:26:36 UTC
BMDB IDBMDB0009165
Secondary Accession Numbers
  • BMDB09165
Metabolite Identification
Common NamePE(18:3(9Z,12Z,15Z)/20:2(11Z,14Z))
DescriptionPE(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)), also known as pe(18:3(9z,12z,15z)/20:2(11z,14z)) or PE(18:3/20:2), 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. Thus, PE(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)) is considered to be a glycerophosphoethanolamine lipid molecule. PE(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PE(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)) participates in a number of enzymatic reactions, within cattle. In particular, PE(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)) can be biosynthesized from PS(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)); which is mediated by the enzyme phosphatidylserine decarboxylase. Furthermore, Cytidine monophosphate and PE(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)) can be biosynthesized from CDP-ethanolamine and DG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Furthermore, Cytidine monophosphate and PE(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)) can be biosynthesized from CDP-ethanolamine and DG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Finally, PE(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)) can be biosynthesized from PS(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)) through the action of the enzyme phosphatidylserine decarboxylase. In cattle, PE(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)) pathway and phosphatidylcholine biosynthesis PC(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-a-Linolenoyl-2-eicosadienoyl-sn-glycero-3-phosphoethanolamineHMDB
Phophatidylethanolamine(38:5)HMDB
Phophatidylethanolamine(18:3/20:2)HMDB
PE(18:3/20:2)HMDB
GPEtn(18:3/20:2)HMDB
PE(38:5)HMDB
1-(9Z,12Z,15Z-Octadeatrienoyl)-2-(11Z,14Z-eicosadienoyl)-sn-glycero-3-phosphoethanolamineHMDB
GPEtn(38:5)HMDB
PE(18:3(9Z,12Z,15Z)/20:2(11Z,14Z))Lipid Annotator
Chemical FormulaC43H76NO8P
Average Molecular Weight766.0392
Monoisotopic Molecular Weight765.530854925
IUPAC Name(2-aminoethoxy)[(2R)-2-[(11Z,14Z)-icosa-11,14-dienoyloxy]-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-2-[(11Z,14Z)-icosa-11,14-dienoyloxy]-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCC\C=C/C\C=C/CCCCC
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/h6,8,11-14,17-19,21,41H,3-5,7,9-10,15-16,20,22-40,44H2,1-2H3,(H,47,48)/b8-6-,13-11-,14-12-,19-17-,21-18-/t41-/m1/s1
InChI KeyFGAIGMYJGVYYEI-GYEARLHBSA-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 Descriptors
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
logP8.73ALOGPS
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
Polarizability90.95 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-0011000900-6342824d2da3f702fd06View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0011000900-6342824d2da3f702fd06View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bvi-0399410600-4986fc654950d9ebbb2eView 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-0003419700-745def48f2279d72fb8eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0003419300-1ccb208a89cfa83430aeView 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-fff2545eb66645067222View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0003419300-5546ba28c9c906ba839cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0011000900-3561f9a25e30578c2b0bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0011000900-3561f9a25e30578c2b0bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bvi-0399410600-10aec6a7d702d8d2253cView 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-d79f0305bf1fce44e41fView 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 IDHMDB0009165
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB026355
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52924429
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(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/0:0) → Cytidine monophosphate + PE(18:3(9Z,12Z,15Z)/20:2(11Z,14Z))details