Showing metabocard for PE(22:2(13Z,16Z)/16:0) (BMDB0009550)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:45:12 UTC
Update Date2020-05-11 19:42:38 UTC
BMDB IDBMDB0009550
Secondary Accession Numbers
  • BMDB09550
Metabolite Identification
Common NamePE(22:2(13Z,16Z)/16:0)
DescriptionPE(22:2(13Z,16Z)/16:0) 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)/16:0), in particular, consists of one 13Z,16Z-docosadienoyl chain to the C-1 atom, and one hexadecanoyl 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(38:2)Lipid Annotator, HMDB
Phophatidylethanolamine(22:2/16:0)Lipid Annotator, HMDB
PE(22:2/16:0)Lipid Annotator, HMDB
GPEtn(38:2)Lipid Annotator, HMDB
PE(22:2(13Z,16Z)/16:0)Lipid Annotator
Phophatidylethanolamine(38:2)Lipid Annotator, HMDB
GPEtn(22:2/16:0)Lipid Annotator, HMDB
1-(13Z,16Z-docosadienoyl)-2-hexadecanoyl-sn-glycero-3-phosphoethanolamineLipid Annotator, HMDB
1-docosadienoyl-2-palmitoyl-sn-glycero-3-phosphoethanolamineLipid Annotator, HMDB
Chemical FormulaC43H82NO8P
Average Molecular Weight772.0868
Monoisotopic Molecular Weight771.577805117
IUPAC Name(2-aminoethoxy)[(2R)-3-[(13Z,16Z)-docosa-13,16-dienoyloxy]-2-(hexadecanoyloxy)propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-3-[(13Z,16Z)-docosa-13,16-dienoyloxy]-2-(hexadecanoyloxy)propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCCC\C=C/C\C=C/CCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C43H82NO8P/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-25-27-29-31-33-35-42(45)49-39-41(40-51-53(47,48)50-38-37-44)52-43(46)36-34-32-30-28-26-23-16-14-12-10-8-6-4-2/h11,13,17-18,41H,3-10,12,14-16,19-40,44H2,1-2H3,(H,47,48)/b13-11-,18-17-/t41-/m1/s1
InChI KeyXNZHFYSLNIZKJP-PYPPRJKTSA-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
logP9.18ALOGPS
logP12.39ChemAxon
logS-7.2ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area134.38 ŲChemAxon
Rotatable Bond Count43ChemAxon
Refractivity220.84 m³·mol⁻¹ChemAxon
Polarizability95.34 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, Negativesplash10-00di-0011000900-c73611c9b1a20b6fc3a0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0011000900-c73611c9b1a20b6fc3a0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abr-0399330600-8be05b9c8ed97c476817View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000001900-6c7e06d23a611a3c1e7aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0089-0003339700-aac288f626912c3547a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0003339300-a669ef0a7f5377944af7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000001900-bae13b9b3cc7d7e251d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0089-0003339700-bb3f43a341ab648d04b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0003339300-2166784be86134fc52ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0011000900-7b32ef39e5c07be3614fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0011000900-7b32ef39e5c07be3614fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abr-0399330600-fc372d8c3a85552e7a78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000001900-d3c5ab252c393ddcfcf0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f6x-0000001900-734c95f48b4fb6e56406View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0100201900-8f0c0cdbc99043561da0View 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 IDHMDB0009550
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB026740
KNApSAcK IDNot Available
Chemspider ID24768994
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52924778
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available