Showing metabocard for PE(20:3(8Z,11Z,14Z)/24:0) (BMDB0009376)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-10-03 17:41:27 UTC
Update Date2020-05-21 16:26:44 UTC
BMDB IDBMDB0009376
Secondary Accession Numbers
  • BMDB09376
Metabolite Identification
Common NamePE(20:3(8Z,11Z,14Z)/24:0)
DescriptionPE(20:3(8Z,11Z,14Z)/24:0), also known as GPEtn(20:3/24:0) or GPEtn(44:3), 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(20:3(8Z,11Z,14Z)/24:0) is possibly soluble (in water) and a very strong basic compound (based on its pKa). PE(20:3(8Z,11Z,14Z)/24:0) participates in a number of enzymatic reactions, within cattle. In particular, PE(20:3(8Z,11Z,14Z)/24:0) can be biosynthesized from PS(20:3(8Z,11Z,14Z)/24:0); which is mediated by the enzyme phosphatidylserine decarboxylase. Furthermore, Cytidine monophosphate and PE(20:3(8Z,11Z,14Z)/24:0) can be biosynthesized from CDP-ethanolamine and DG(20:3(8Z,11Z,14Z)/24:0/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Furthermore, Cytidine monophosphate and PE(20:3(8Z,11Z,14Z)/24:0) can be biosynthesized from CDP-ethanolamine and DG(20:3(8Z,11Z,14Z)/24:0/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Finally, PE(20:3(8Z,11Z,14Z)/24:0) can be biosynthesized from PS(20:3(8Z,11Z,14Z)/24:0); which is mediated by the enzyme phosphatidylserine decarboxylase. In cattle, PE(20:3(8Z,11Z,14Z)/24:0) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(20:3(8Z,11Z,14Z)/24:0) pathway and phosphatidylcholine biosynthesis PC(20:3(8Z,11Z,14Z)/24:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Homo-g-linolenoyl-2-lignoceroyl-sn-glycero-3-phosphoethanolamineHMDB
1-Homo-gamma-linolenoyl-2-lignoceroyl-sn-glycero-3-phosphoethanolamineHMDB
GPEtn(20:3/24:0)HMDB
GPEtn(20:3n6/24:0)HMDB
GPEtn(20:3W6/24:0)HMDB
GPEtn(44:3)HMDB
PE(20:3/24:0)HMDB
PE(20:3N6/24:0)HMDB
PE(20:3W6/24:0)HMDB
PE(44:3)HMDB
Phophatidylethanolamine(20:3/24:0)HMDB
Phophatidylethanolamine(20:3n6/24:0)HMDB
Phophatidylethanolamine(20:3W6/24:0)HMDB
Phophatidylethanolamine(44:3)HMDB
1-(8Z,11Z,14Z-Eicosatrienoyl)-2-tetracosanoyl-sn-glycero-3-phosphoethanolamineHMDB
PE(20:3(8Z,11Z,14Z)/24:0)Lipid Annotator
Chemical FormulaC49H92NO8P
Average Molecular Weight854.2304
Monoisotopic Molecular Weight853.656055437
IUPAC Name(2-aminoethoxy)[(2R)-3-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]-2-(tetracosanoyloxy)propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-3-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]-2-(tetracosanoyloxy)propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCC\C=C/C\C=C/C\C=C/CCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C49H92NO8P/c1-3-5-7-9-11-13-15-17-19-21-22-23-24-26-28-30-32-34-36-38-40-42-49(52)58-47(46-57-59(53,54)56-44-43-50)45-55-48(51)41-39-37-35-33-31-29-27-25-20-18-16-14-12-10-8-6-4-2/h12,14,18,20,27,29,47H,3-11,13,15-17,19,21-26,28,30-46,50H2,1-2H3,(H,53,54)/b14-12-,20-18-,29-27-/t47-/m1/s1
InChI KeyMAYDWIZSJUSDNQ-GMVQFAJDSA-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
logP9.83ALOGPS
logP14.7ChemAxon
logS-7.3ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area134.38 ŲChemAxon
Rotatable Bond Count48ChemAxon
Refractivity249.57 m³·mol⁻¹ChemAxon
Polarizability106.77 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, Negativesplash10-0udi-0003000090-289979d438b811f51243View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0003000090-289979d438b811f51243View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-15mi-0109020030-dd0aabf06b8b6adaeabcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000190-f25f486d6d47f13e3826View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ik9-0001340970-8d7d424c3c7a57195ae7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0001340930-306cac732d87246a0efdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000190-fccec362e4d7b3c7c9fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000000190-7aee38c99dc40e08da76View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0100110190-ddee02612aea63c42b3fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000190-196de677ddeba022bb3fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ik9-0001340970-42a9c72df53e8c7248f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0001340930-4ec61ac25b62ad627993View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0003000090-020989c26d0c0e99f8e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0003000090-020989c26d0c0e99f8e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-1000-0109020030-f4dc714348faab55df5eView 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 IDHMDB0009376
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB026566
KNApSAcK IDNot Available
Chemspider ID24768827
KEGG Compound IDC00350
BioCyc IDL-1-PHOSPHATIDYL-ETHANOLAMINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53479781
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(20:3(8Z,11Z,14Z)/24:0/0:0) → Cytidine monophosphate + PE(20:3(8Z,11Z,14Z)/24:0)details