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Record Information
Version1.0
Creation Date2016-10-03 17:35:16 UTC
Update Date2020-05-21 16:26:32 UTC
BMDB IDBMDB0009076
Secondary Accession Numbers
  • BMDB09076
Metabolite Identification
Common NamePE(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))
DescriptionPE(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)), also known as PE(40:6) or GPEtn(18:1/22:5), 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(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) is possibly soluble (in water) and a very strong basic compound (based on its pKa). PE(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) participates in a number of enzymatic reactions, within cattle. In particular, PE(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) can be biosynthesized from PS(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) through its interaction with the enzyme phosphatidylserine decarboxylase. Furthermore, Cytidine monophosphate and PE(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) can be biosynthesized from CDP-ethanolamine and DG(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Furthermore, Cytidine monophosphate and PE(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) can be biosynthesized from CDP-ethanolamine and DG(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Finally, PE(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) can be biosynthesized from PS(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) through the action of the enzyme phosphatidylserine decarboxylase. In cattle, PE(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) pathway and phosphatidylcholine biosynthesis PC(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) pathway.
Structure
Thumb
Synonyms
ValueSource
1-Oleoyl-2-osbondoyl-sn-glycero-3-phosphoethanolamineHMDB
PE(40:6)HMDB
GPEtn(18:1/22:5)HMDB
Phophatidylethanolamine(40:6)HMDB
Phophatidylethanolamine(18:1/22:5)HMDB
GPEtn(40:6)HMDB
1-(9Z-Octadecenoyl)-2-(4Z,7Z,10Z,13Z,16Z-docosapentaenoyl)-sn-glycero-3-phosphoethanolamineHMDB
PE(18:1/22:5)HMDB
PE(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))Lipid Annotator
Chemical FormulaC45H78NO8P
Average Molecular Weight792.0765
Monoisotopic Molecular Weight791.546504989
IUPAC Name(2-aminoethoxy)[(2R)-2-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-2-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]-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/CCCCC
InChI Identifier
InChI=1S/C45H78NO8P/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/h11,13,17-19,21-23,26,28,32,34,43H,3-10,12,14-16,20,24-25,27,29-31,33,35-42,46H2,1-2H3,(H,49,50)/b13-11-,19-17-,22-21-,23-18-,28-26-,34-32-/t43-/m1/s1
InChI KeyRXUUAZTYMDTFAY-LMJZRCAFSA-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
logP9.01ALOGPS
logP11.84ChemAxon
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 Count41ChemAxon
Refractivity234.51 m³·mol⁻¹ChemAxon
Polarizability94.24 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0011000900-5f8cc095d6d77759175dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0011000900-5f8cc095d6d77759175dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-005c-0399330600-0c994df8253d2d88347dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000001900-ec03134855921e78879dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udl-0003339700-43a8e7a665cc6ee24c8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0003339300-400fa835fc10fbadb167View 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 IDHMDB0009076
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 Compound53479653
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

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)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) → Cytidine monophosphate + PE(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))details