Showing metabocard for PE(24:1(15Z)/22:2(13Z,16Z)) (BMDB0009767)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:49:51 UTC
Update Date2020-05-11 19:45:38 UTC
BMDB IDBMDB0009767
Secondary Accession Numbers
  • BMDB09767
Metabolite Identification
Common NamePE(24:1(15Z)/22:2(13Z,16Z))
DescriptionPE(24:1(15Z)/22:2(13Z,16Z)) 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(24:1(15Z)/22:2(13Z,16Z)), in particular, consists of one 15Z-tetracosenoyl chain to the C-1 atom, and one 13Z,16Z-docosadienoyl 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(46:3)Lipid Annotator, HMDB
1-nervonoyl-2-docosadienoyl-sn-glycero-3-phosphoethanolamineLipid Annotator, HMDB
Phophatidylethanolamine(24:1/22:2)Lipid Annotator, HMDB
GPEtn(46:3)Lipid Annotator, HMDB
PE(24:1(15Z)/22:2(13Z,16Z))Lipid Annotator
Phophatidylethanolamine(46:3)Lipid Annotator, HMDB
PE(24:1/22:2)Lipid Annotator, HMDB
1-(15Z-tetracosanoyl)-2-(13Z,16Z-docosadienoyl)-sn-glycero-3-phosphoethanolamineLipid Annotator, HMDB
GPEtn(24:1/22:2)Lipid Annotator, HMDB
Chemical FormulaC51H96NO8P
Average Molecular Weight882.2836
Monoisotopic Molecular Weight881.687355565
IUPAC Name(2-aminoethoxy)[(2R)-2-[(13Z,16Z)-docosa-13,16-dienoyloxy]-3-[(15Z)-tetracos-15-enoyloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-2-[(13Z,16Z)-docosa-13,16-dienoyloxy]-3-[(15Z)-tetracos-15-enoyloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCC\C=C/CCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C51H96NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-24-26-27-29-31-33-35-37-39-41-43-50(53)57-47-49(48-59-61(55,56)58-46-45-52)60-51(54)44-42-40-38-36-34-32-30-28-25-22-20-18-16-14-12-10-8-6-4-2/h12,14,17-20,49H,3-11,13,15-16,21-48,52H2,1-2H3,(H,55,56)/b14-12-,19-17-,20-18-/t49-/m1/s1
InChI KeyRNFHVQZPAYLGCQ-DGQABRSQSA-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
logP9.92ALOGPS
logP15.59ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area134.38 ŲChemAxon
Rotatable Bond Count50ChemAxon
Refractivity258.77 m³·mol⁻¹ChemAxon
Polarizability110.77 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, Negativesplash10-001i-0003000090-b884d20f895084850b0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0003000090-b884d20f895084850b0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-015r-0109030030-2f14c4aca040f7e9bce2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000190-e2cc513fdd423a3ee6dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-0001160970-c86fbb234713d5a9f62cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0001160930-2b28ce8422c357eb3bbaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000109-87d44aa06464c6161466View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w29-0000000229-90f17d3861bd4349c289View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0100110191-b234a3e4a1ac69895759View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0003000090-9fec3b67ed2601474edcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0003000090-9fec3b67ed2601474edcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-015r-0109030030-399b25f6f6f5199a9b5bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000190-dd8bc1aaf6184b1d1a87View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-0001160970-0f2cd05b4cf1d4ff500dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0001160930-2a353d9259a2b8062ea4View 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 IDHMDB0009767
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24769207
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480039
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available