Showing metabocard for PE(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)) (BMDB0009141)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-10-03 17:36:34 UTC
Update Date2020-05-21 16:26:35 UTC
BMDB IDBMDB0009141
Secondary Accession Numbers
  • BMDB09141
Metabolite Identification
Common NamePE(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))
DescriptionPE(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)), also known as GPEtn(18:3/22:4) or GPEtn(40:7), 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(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)) is considered to be a glycerophosphoethanolamine lipid molecule. PE(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PE(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)) participates in a number of enzymatic reactions, within cattle. In particular, PE(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)) can be biosynthesized from PS(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)); which is mediated by the enzyme phosphatidylserine decarboxylase. Furthermore, Cytidine monophosphate and PE(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)) can be biosynthesized from CDP-ethanolamine and DG(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Furthermore, Cytidine monophosphate and PE(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)) can be biosynthesized from CDP-ethanolamine and DG(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Finally, PE(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)) can be biosynthesized from PS(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)) through the action of the enzyme phosphatidylserine decarboxylase. In cattle, PE(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)) pathway and phosphatidylcholine biosynthesis PC(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-g-Linolenoyl-2-adrenoyl-sn-glycero-3-phosphoethanolamineHMDB
1-gamma-Linolenoyl-2-adrenoyl-sn-glycero-3-phosphoethanolamineHMDB
GPEtn(18:3/22:4)HMDB
GPEtn(18:3n6/22:4n6)HMDB
GPEtn(18:3W6/22:4W6)HMDB
GPEtn(40:7)HMDB
PE(18:3/22:4)HMDB
PE(18:3N6/22:4N6)HMDB
PE(18:3W6/22:4W6)HMDB
PE(40:7)HMDB
Phophatidylethanolamine(18:3/22:4)HMDB
Phophatidylethanolamine(18:3n6/22:4n6)HMDB
Phophatidylethanolamine(18:3W6/22:4W6)HMDB
Phophatidylethanolamine(40:7)HMDB
1-(6Z,9Z,12Z-Octadecatrienoyl)-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycero-3-phosphoethanolamineHMDB
PE(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))Lipid Annotator
Chemical FormulaC45H76NO8P
Average Molecular Weight790.0606
Monoisotopic Molecular Weight789.530854925
IUPAC Name(2-aminoethoxy)[(2R)-2-[(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoyloxy]-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-2-[(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoyloxy]-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C45H76NO8P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-45(48)54-43(42-53-55(49,50)52-40-39-46)41-51-44(47)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h11-14,17-19,21-23,26-29,43H,3-10,15-16,20,24-25,30-42,46H2,1-2H3,(H,49,50)/b13-11-,14-12-,19-17-,22-21-,23-18-,28-26-,29-27-/t43-/m1/s1
InChI KeyCJBHVSFSJIZOSI-CCQVWZKGSA-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
logP8.61ALOGPS
logP11.47ChemAxon
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 Count40ChemAxon
Refractivity235.63 m³·mol⁻¹ChemAxon
Polarizability92.54 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, Negativesplash10-000i-0011000900-2f10fbcdd1c41ccb0d61View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0011000900-2f10fbcdd1c41ccb0d61View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-005i-0399330600-360d9209ce28879cf593View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000001900-f589f0a7bb6b411ef675View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0005-0003339700-0d460fb4cf2902a50eaaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0003339300-01c37776a8486983839eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0011000900-1c7b4a3fc6593ee5fd60View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0011000900-1c7b4a3fc6593ee5fd60View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-005i-0399330600-073fdb2fcd8fc2263c53View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000001090-48f5d3082db8beb7d972View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000002290-a32d09d9a3ee2eb21d57View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0100301910-b86efb5f6c9c376ae4d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000001900-12f6afb806b6f1d2e121View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0005-0003339700-3fe9a2fb9cd88a73bb71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0003339300-2c9830a9174263498cebView 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 IDHMDB0009141
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB026331
KNApSAcK IDNot Available
Chemspider ID24768604
KEGG Compound IDC00350
BioCyc IDL-1-PHOSPHATIDYL-ETHANOLAMINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52924409
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(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0) → Cytidine monophosphate + PE(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))details