Showing metabocard for PE(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (BMDB0009078)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 17:35:18 UTC
Update Date2020-05-21 16:28:15 UTC
BMDB IDBMDB0009078
Secondary Accession Numbers
  • BMDB09078
Metabolite Identification
Common NamePE(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
DescriptionPE(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), also known as pe(18:1(9z)/22:6(4z,7z,10z,13z,16z,19z)) or GPEtn(18:1/22:6), 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(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is considered to be a glycerophosphoethanolamine lipid molecule. PE(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PE(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) participates in a number of enzymatic reactions, within cattle. In particular, PE(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) can be biosynthesized from PS(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) through the action of the enzyme phosphatidylserine decarboxylase. Furthermore, Cytidine monophosphate and PE(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) can be biosynthesized from CDP-ethanolamine and DG(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Furthermore, Cytidine monophosphate and PE(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) can be biosynthesized from CDP-ethanolamine and DG(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Finally, PE(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) can be biosynthesized from PS(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)); which is catalyzed by the enzyme phosphatidylserine decarboxylase. In cattle, PE(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) pathway and phosphatidylcholine biosynthesis PC(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Phophatidylethanolamine(18:1/22:6)HMDB
GPEtn(18:1/22:6)HMDB
PE(40:7)HMDB
Phophatidylethanolamine(40:7)HMDB
1-Oleoyl-2-docosahexaenoyl-sn-glycero-3-phosphoethanolamineHMDB
GPEtn(40:7)HMDB
1-(9Z-Octadecenoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphoethanolamineHMDB
PE(18:1/22:6)HMDB
PE(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))Lipid Annotator
Chemical FormulaC45H76NO8P
Average Molecular Weight790.0606
Monoisotopic Molecular Weight789.530854925
IUPAC Name(2-aminoethoxy)[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
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/h5,7,11,13,17-19,21-23,26,28,32,34,43H,3-4,6,8-10,12,14-16,20,24-25,27,29-31,33,35-42,46H2,1-2H3,(H,49,50)/b7-5-,13-11-,19-17-,22-21-,23-18-,28-26-,34-32-/t43-/m1/s1
InChI KeyJZSZAGWWWKKXLO-RMEBTJIYSA-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
logP11.47ChemAxon
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
Polarizability92.98 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-0011000900-7fdb7a7ec8ddd5fafb8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0011000900-7fdb7a7ec8ddd5fafb8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-005i-0399330600-e94bbec01d53cfc42080View 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, Positivesplash10-0005-0003339700-2a87d2e0eed136076493View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0003339300-6cdfcdce8a310b3ac43fView 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, Positivesplash10-0005-0003339700-5b9e30ea16c2c2a999dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0003339300-631b7b9a2bfb4fba9093View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0011000900-3f640f8b61ddaf7e346dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0011000900-3f640f8b61ddaf7e346dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-005i-0399330600-8959192a127d58e92644View 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-0100301910-97a460b1555aaef0e719View 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 IDHMDB0009078
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 Compound52922113
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(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) → Cytidine monophosphate + PE(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))details
Enzyme Details
2. Phosphatidylserine decarboxylase proenzyme, mitochondrial
General function:
Not Available
Specific function:
Catalyzes the formation of phosphatidylethanolamine (PtdEtn) from phosphatidylserine (PtdSer). Plays a central role in phospholipid metabolism and in the interorganelle trafficking of phosphatidylserine.
Gene Name:
PISD
Uniprot ID:
Q58DH2
Molecular weight:
47244.0
Reactions
PS(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) → PE(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) + Carbon dioxidedetails