Showing metabocard for PE(22:0/22:4(7Z,10Z,13Z,16Z)) (BMDB0009504)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-10-03 17:44:15 UTC
Update Date2020-05-21 16:26:47 UTC
BMDB IDBMDB0009504
Secondary Accession Numbers
  • BMDB09504
Metabolite Identification
Common NamePE(22:0/22:4(7Z,10Z,13Z,16Z))
DescriptionPE(22:0/22:4(7Z,10Z,13Z,16Z)), also known as pe(22:0/22:4(7z,10z,13z,16z)) or PE(44:4), 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(22:0/22:4(7Z,10Z,13Z,16Z)) is considered to be a glycerophosphoethanolamine lipid molecule. PE(22:0/22:4(7Z,10Z,13Z,16Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PE(22:0/22:4(7Z,10Z,13Z,16Z)) participates in a number of enzymatic reactions, within cattle. In particular, PE(22:0/22:4(7Z,10Z,13Z,16Z)) can be biosynthesized from PS(22:0/22:4(7Z,10Z,13Z,16Z)); which is catalyzed by the enzyme phosphatidylserine decarboxylase. Furthermore, Cytidine monophosphate and PE(22:0/22:4(7Z,10Z,13Z,16Z)) can be biosynthesized from CDP-ethanolamine and DG(22:0/22:4(7Z,10Z,13Z,16Z)/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Furthermore, Cytidine monophosphate and PE(22:0/22:4(7Z,10Z,13Z,16Z)) can be biosynthesized from CDP-ethanolamine and DG(22:0/22:4(7Z,10Z,13Z,16Z)/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Finally, PE(22:0/22:4(7Z,10Z,13Z,16Z)) can be biosynthesized from PS(22:0/22:4(7Z,10Z,13Z,16Z)); which is mediated by the enzyme phosphatidylserine decarboxylase. In cattle, PE(22:0/22:4(7Z,10Z,13Z,16Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(22:0/22:4(7Z,10Z,13Z,16Z)) pathway and phosphatidylcholine biosynthesis PC(22:0/22:4(7Z,10Z,13Z,16Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Phophatidylethanolamine(44:4)HMDB
PE(44:4)HMDB
GPEtn(44:4)HMDB
PE(22:0/22:4)HMDB
Phophatidylethanolamine(22:0/22:4)HMDB
1-Behenoyl-2-adrenoyl-sn-glycero-3-phosphoethanolamineHMDB
1-Docosanoyl-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycero-3-phosphoethanolamineHMDB
GPEtn(22:0/22:4)HMDB
PE(22:0/22:4(7Z,10Z,13Z,16Z))Lipid Annotator
Chemical FormulaC49H90NO8P
Average Molecular Weight852.2146
Monoisotopic Molecular Weight851.640405373
IUPAC Name(2-aminoethoxy)[(2R)-2-[(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoyloxy]-3-(docosanoyloxy)propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-2-[(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoyloxy]-3-(docosanoyloxy)propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C49H90NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-39-41-48(51)55-45-47(46-57-59(53,54)56-44-43-50)58-49(52)42-40-38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h12,14,18,20,24,26,30,32,47H,3-11,13,15-17,19,21-23,25,27-29,31,33-46,50H2,1-2H3,(H,53,54)/b14-12-,20-18-,26-24-,32-30-/t47-/m1/s1
InChI KeyYVOGVSSSJHYLFJ-VOSZABOESA-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
logP9.79ALOGPS
logP14.34ChemAxon
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 Count47ChemAxon
Refractivity250.68 m³·mol⁻¹ChemAxon
Polarizability105.51 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-f60fea1c61ce441f1504View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0003000090-f60fea1c61ce441f1504View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f80-0109030030-4e1c3cf19f7d4f04d370View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000190-51f14322a8d5057e2e4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ik9-0003060970-24f48a9618042d9ce790View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0003060930-c370f5c93d89a4e4ee48View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000000190-999048a83983d494a21aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00e9-0000000190-8ff7d4a79dc6a46609b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0100200190-2d931015d73bdf184a76View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0003000090-f73b9befd7cd478204e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0003000090-f73b9befd7cd478204e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f80-0109030030-901c865e66b66e9d1fadView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000190-b06bbbb4b6d20d48e73cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ik9-0003060970-f7381abcf82fe09862d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0003060930-b974ae3fbcef02f56435View 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 IDHMDB0009504
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB026694
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52924739
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(22:0/22:4(7Z,10Z,13Z,16Z)/0:0) → Cytidine monophosphate + PE(22:0/22:4(7Z,10Z,13Z,16Z))details