Showing metabocard for PE(18:3(9Z,12Z,15Z)/22:1(13Z)) (BMDB0009172)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-10-03 17:37:11 UTC
Update Date2020-05-21 16:26:36 UTC
BMDB IDBMDB0009172
Secondary Accession Numbers
  • BMDB09172
Metabolite Identification
Common NamePE(18:3(9Z,12Z,15Z)/22:1(13Z))
DescriptionPE(18:3(9Z,12Z,15Z)/22:1(13Z)), also known as GPEtn(40:4) or GPEtn(18:3/22:1), 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(18:3(9Z,12Z,15Z)/22:1(13Z)) is possibly soluble (in water) and a very strong basic compound (based on its pKa). PE(18:3(9Z,12Z,15Z)/22:1(13Z)) participates in a number of enzymatic reactions, within cattle. In particular, PE(18:3(9Z,12Z,15Z)/22:1(13Z)) can be biosynthesized from PS(18:3(9Z,12Z,15Z)/22:1(13Z)) through its interaction with the enzyme phosphatidylserine decarboxylase. Furthermore, Cytidine monophosphate and PE(18:3(9Z,12Z,15Z)/22:1(13Z)) can be biosynthesized from CDP-ethanolamine and DG(18:3(9Z,12Z,15Z)/22:1(13Z)/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Furthermore, Cytidine monophosphate and PE(18:3(9Z,12Z,15Z)/22:1(13Z)) can be biosynthesized from CDP-ethanolamine and DG(18:3(9Z,12Z,15Z)/22:1(13Z)/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Finally, PE(18:3(9Z,12Z,15Z)/22:1(13Z)) can be biosynthesized from PS(18:3(9Z,12Z,15Z)/22:1(13Z)); which is catalyzed by the enzyme phosphatidylserine decarboxylase. In cattle, PE(18:3(9Z,12Z,15Z)/22:1(13Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(18:3(9Z,12Z,15Z)/22:1(13Z)) pathway and phosphatidylcholine biosynthesis PC(18:3(9Z,12Z,15Z)/22:1(13Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
GPEtn(40:4)HMDB
PE(40:4)HMDB
GPEtn(18:3/22:1)HMDB
Phophatidylethanolamine(40:4)HMDB
PE(18:3/22:1)HMDB
1-a-Linolenoyl-2-erucoyl-sn-glycero-3-phosphoethanolamineHMDB
1-(9Z,12Z,15Z-Octadeatrienoyl)-2-(13Z-docosenoyl)-sn-glycero-3-phosphoethanolamineHMDB
Phophatidylethanolamine(18:3/22:1)HMDB
PE(18:3(9Z,12Z,15Z)/22:1(13Z))Lipid Annotator
Chemical FormulaC45H82NO8P
Average Molecular Weight796.1082
Monoisotopic Molecular Weight795.577805117
IUPAC Name(2-aminoethoxy)[(2R)-2-[(13Z)-docos-13-enoyloxy]-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-2-[(13Z)-docos-13-enoyloxy]-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)CCCCCCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C45H82NO8P/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/h6,8,12,14,17-19,23,43H,3-5,7,9-11,13,15-16,20-22,24-42,46H2,1-2H3,(H,49,50)/b8-6-,14-12-,19-17-,23-18-/t43-/m1/s1
InChI KeyDSZLDVIMYQKWGY-JOIVCNAYSA-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
logP9.29ALOGPS
logP12.56ChemAxon
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 Count43ChemAxon
Refractivity232.28 m³·mol⁻¹ChemAxon
Polarizability96.78 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, Negativesplash10-0006-0011000900-adc25c783283c04570ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0011000900-adc25c783283c04570ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0053-0399330600-b3a62656f76cfb5ffe2bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000001900-e4c6e7b2865871b4c0cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-0003339700-376a0137a7d778308ea1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0003339300-377c5b4059d70c531775View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0011000900-be91a02dcbbeb19b4d0eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0011000900-be91a02dcbbeb19b4d0eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0053-0399330600-e44db713b077474120b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000001090-7c25145fd7409b75812bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016r-0000002290-7dd7dedffbe696e1ba65View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0100301910-73f78dbae659fdeabd59View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000001900-82b1b3b32ab43ea49702View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-0003339700-1a086484983d84864594View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0003339300-90be147c02a9d4613951View 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 IDHMDB0009172
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 Compound53479688
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)/22:1(13Z)/0:0) → Cytidine monophosphate + PE(18:3(9Z,12Z,15Z)/22:1(13Z))details