Showing metabocard for PE(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (BMDB0009137)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-10-03 17:36:29 UTC
Update Date2020-05-21 16:26:35 UTC
BMDB IDBMDB0009137
Secondary Accession Numbers
  • BMDB09137
Metabolite Identification
Common NamePE(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))
DescriptionPE(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)), also known as PE(18:3/20:5) or PE(38:8), 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)/20:5(5Z,8Z,11Z,14Z,17Z)) is considered to be a glycerophosphoethanolamine lipid molecule. PE(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PE(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) participates in a number of enzymatic reactions, within cattle. In particular, PE(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) can be biosynthesized from PS(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)); which is catalyzed by the enzyme phosphatidylserine decarboxylase. Furthermore, Cytidine monophosphate and PE(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) can be biosynthesized from CDP-ethanolamine and DG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Furthermore, Cytidine monophosphate and PE(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) can be biosynthesized from CDP-ethanolamine and DG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Finally, PE(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) can be biosynthesized from PS(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) through its interaction with the enzyme phosphatidylserine decarboxylase. In cattle, PE(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) pathway and phosphatidylcholine biosynthesis PC(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
PE(18:3/20:5)HMDB
PE(38:8)HMDB
GPEtn(38:8)HMDB
1-g-Linolenoyl-2-eicosapentaenoyl-sn-glycero-3-phosphoethanolamineHMDB
GPEtn(18:3/20:5)HMDB
Phophatidylethanolamine(18:3/20:5)HMDB
1-(6Z,9Z,12Z-Octadecatrienoyl)-2-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycero-3-phosphoethanolamineHMDB
Phophatidylethanolamine(38:8)HMDB
PE(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))Lipid Annotator
Chemical FormulaC43H70NO8P
Average Molecular Weight759.9916
Monoisotopic Molecular Weight759.483904733
IUPAC Name(2-aminoethoxy)[(2R)-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxy]phosphinic acid
Traditional NamePPP
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)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C43H70NO8P/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/h5,7,11-14,17-19,21-22,24-25,27-28,30,41H,3-4,6,8-10,15-16,20,23,26,29,31-40,44H2,1-2H3,(H,47,48)/b7-5-,13-11-,14-12-,19-17-,21-18-,24-22-,27-25-,30-28-/t41-/m1/s1
InChI KeyLAXOJOQXUPOBND-HSHOEZBASA-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
logP7.82ALOGPS
logP10.22ChemAxon
logS-6.9ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area134.38 ŲChemAxon
Rotatable Bond Count37ChemAxon
Refractivity227.54 m³·mol⁻¹ChemAxon
Polarizability86.9 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, Negativesplash10-0a4i-0011000900-8231bfbd50c93b5c75f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0011000900-8231bfbd50c93b5c75f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zi0-0399600600-1e514fe4b67f5bae5a66View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000001900-258072797f24bff0cbb4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02t9-0003419700-6c9f49308fa57e4d2e4bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0003419300-3b5ab365caf57da88052View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000001900-3b0b28ecd0c257ba9637View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000001900-a53c1cd07c6b9b831b4fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0100201900-5157e9bd45b72ba37dadView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0011000900-4214950f756660d2dfe0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0011000900-4214950f756660d2dfe0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zi0-0399600600-6c32f6fa98773f63a0eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000001900-00d0b37fd153e95db980View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02t9-0003419700-253ae5286ab9772df2e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0003419300-2a95eb64b694d755dd8eView 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 IDHMDB0009137
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 Compound52924404
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)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0) → Cytidine monophosphate + PE(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))details