Showing metabocard for PE(22:2(13Z,16Z)/22:0) (BMDB0009567)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:45:33 UTC
Update Date2020-05-11 19:42:52 UTC
BMDB IDBMDB0009567
Secondary Accession Numbers
  • BMDB09567
Metabolite Identification
Common NamePE(22:2(13Z,16Z)/22:0)
DescriptionPE(22:2(13Z,16Z)/22:0) 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(22:2(13Z,16Z)/22:0), in particular, consists of one 13Z,16Z-docosadienoyl chain to the C-1 atom, and one docosanoyl 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
PE(22:2/22:0)HMDB
Phophatidylethanolamine(22:2/22:0)HMDB
GPEtn(22:2/22:0)HMDB
1-Docosadienoyl-2-behenoyl-sn-glycero-3-phosphoethanolamineHMDB
GPEtn(44:2)HMDB
PE(44:2)HMDB
1-(13Z,16Z-Docosadienoyl)-2-docosanoyl-sn-glycero-3-phosphoethanolamineHMDB
Phophatidylethanolamine(44:2)HMDB
PE(22:2(13Z,16Z)/22:0)Lipid Annotator
Chemical FormulaC49H94NO8P
Average Molecular Weight856.2463
Monoisotopic Molecular Weight855.671705501
IUPAC Name(2-aminoethoxy)[(2R)-3-[(13Z,16Z)-docosa-13,16-dienoyloxy]-2-(docosanoyloxy)propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-3-[(13Z,16Z)-docosa-13,16-dienoyloxy]-2-(docosanoyloxy)propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCCC\C=C/C\C=C/CCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C49H94NO8P/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/h11,13,17,19,47H,3-10,12,14-16,18,20-46,50H2,1-2H3,(H,53,54)/b13-11-,19-17-/t47-/m1/s1
InChI KeyINEGCSSQPPHJAY-GIBQJYIPSA-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
logP9.81ALOGPS
logP15.06ChemAxon
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 Count49ChemAxon
Refractivity248.45 m³·mol⁻¹ChemAxon
Polarizability108.21 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0003000090-cba1995dab0d51b66a13View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0003000090-cba1995dab0d51b66a13View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0109030030-1718a9570bac883b7c29View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000190-dcdf1ccf743b54145b5cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-066r-0003060970-a02498a707532cdb2d53View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0003060930-928b9be9ca23c72c4efbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000190-cb7782176473c22144d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-066r-0003060970-65af89afeb5c735aafc6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0003060930-6a355c8e48df53dc64aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000190-7de1692df5664ad6b2cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004r-0000000190-33d78b7e143098200596View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0100200190-7fc398877e5632cba8c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0003000090-4db8bd601a5233e2d047View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0003000090-4db8bd601a5233e2d047View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0109030030-94c7bc9168d35493646aView 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 IDHMDB0009567
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB026757
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52924798
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available