Showing metabocard for PE(22:5(4Z,7Z,10Z,13Z,16Z)/20:3(5Z,8Z,11Z)) (BMDB0009628)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:46:54 UTC
Update Date2020-05-11 19:43:42 UTC
BMDB IDBMDB0009628
Secondary Accession Numbers
  • BMDB09628
Metabolite Identification
Common NamePE(22:5(4Z,7Z,10Z,13Z,16Z)/20:3(5Z,8Z,11Z))
DescriptionPE(22:5(4Z,7Z,10Z,13Z,16Z)/20:3(5Z,8Z,11Z)) is a phosphatidylethanolamine. It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 atoms. PE(22:5(4Z,7Z,10Z,13Z,16Z)/20:3(5Z,8Z,11Z)), in particular, consists of one 4Z,7Z,10Z,13Z,16Z-docosapentaenoyl chain to the C-1 atom, and one 5Z,8Z,11Z-eicosatrienoyl to the C-2 atom. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Osbondoyl-2-meadoyl-sn-glycero-3-phosphoethanolamineHMDB
Phophatidylethanolamine(42:8)HMDB
PE(22:5/20:3)HMDB
GPEtn(22:5/20:3)HMDB
Phophatidylethanolamine(22:5/20:3)HMDB
PE(42:8)HMDB
1-(4Z,7Z,10Z,13Z,16Z-Docosapentaenoyl)-2-(5Z,8Z,11Z-eicosatrienoyl)-sn-glycero-3-phosphoethanolamineHMDB
GPEtn(42:8)HMDB
PE(22:5(4Z,7Z,10Z,13Z,16Z)/20:3(5Z,8Z,11Z))Lipid Annotator
Chemical FormulaC47H78NO8P
Average Molecular Weight816.0979
Monoisotopic Molecular Weight815.546504989
IUPAC Name(2-aminoethoxy)[(2R)-3-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-3-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC)(COP(O)(=O)OCCN)OC(=O)CCC\C=C/C\C=C/C\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C47H78NO8P/c1-3-5-7-9-11-13-15-17-19-21-22-24-25-27-29-31-33-35-37-39-46(49)53-43-45(44-55-57(51,52)54-42-41-48)56-47(50)40-38-36-34-32-30-28-26-23-20-18-16-14-12-10-8-6-4-2/h11,13,17-20,22,24,26-29,32-35,45H,3-10,12,14-16,21,23,25,30-31,36-44,48H2,1-2H3,(H,51,52)/b13-11-,19-17-,20-18-,24-22-,28-26-,29-27-,34-32-,35-33-/t45-/m1/s1
InChI KeyNCAIHLKBGGDTEK-HIZOEKCOSA-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
logP8.79ALOGPS
logP12ChemAxon
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
Refractivity245.95 m³·mol⁻¹ChemAxon
Polarizability95.21 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, Negativesplash10-03di-0003000090-10ff75edac76dd528e07View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0003000090-10ff75edac76dd528e07View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bxr-0109020030-bc8ac8a26e2e19643a37View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000001190-d62122a10fa208d470b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00or-0003149160-30ffe56cd0273c1da460View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0003149110-831e5a51d09674021dbbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000001190-689500b4c5a9846566e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00or-0003149160-93e96f643d5bb692ec67View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0003149110-0754962ccaa146fd5689View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0003000090-52cee48794e65e8e4af9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0003000090-52cee48794e65e8e4af9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bxr-0109020030-5947a99d6994b309ff11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000001090-2c80d86c7b8a88878684View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000j-0000002290-9227a6968af23594dd64View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0100301910-03836c72ad543e8ecd86View 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 IDHMDB0009628
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB026818
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53479924
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available