Record Information
Version1.0
Creation date2011-09-21 01:16:56 UTC
Update date2015-07-21 06:58:55 UTC
Primary IDFDB026886
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))
DescriptionPE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)) is a phosphatidylethanolamine (PE or GPEtn). 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 at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)), in particular, consists of one chain of docosahexaenoic acid at the C-1 position and one chain of arachidonic acid at the C-2 position. The docosahexaenoic acid moiety is derived from fish oils, while the arachidonic acid moiety is derived from animal fats and eggs. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. 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. [HMDB]
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
1-Docosahexaenoyl-2-arachidonoyl-sn-glycero-3-oethanolamineHMDB
1-docosahexaenoyl-2-arachidonoyl-sn-glycero-3-phosphoethanolaminehmdb
GPEtn(22:6/20:4)HMDB
GPEtn(22:6n3/20:4n6)hmdb
GPEtn(22:6w3/20:4w6)hmdb
PE(22:6/20:4)HMDB
PE(22:6n3/20:4n6)hmdb
PE(22:6w3/20:4w6)hmdb
Phophatidylethanolamine(22:6/20:4)HMDB
Phophatidylethanolamine(22:6n3/20:4n6)hmdb
Phophatidylethanolamine(22:6w3/20:4w6)hmdb
Predicted Properties
PropertyValueSource
Water Solubility9.5e-05 g/LALOGPS
logP8.07ALOGPS
logP11.28ChemAxon
logS-6.9ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area134.38 ŲChemAxon
Rotatable Bond Count39ChemAxon
Refractivity248.18 m³·mol⁻¹ChemAxon
Polarizability92.84 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC47H74NO8P
IUPAC name(2-aminoethoxy)[(2R)-3-(docosa-4,7,10,13,16,19-hexaenoyloxy)-2-(icosa-5,8,11,14-tetraenoyloxy)propoxy]phosphinic acid
InChI IdentifierInChI=1S/C47H74NO8P/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/h5,7,11-14,17-20,22,24,26-29,32-35,45H,3-4,6,8-10,15-16,21,23,25,30-31,36-44,48H2,1-2H3,(H,51,52)/t45-/m1/s1
InChI KeyZEMOTHAYXPPBGC-WBVITSLISA-N
Isomeric SMILES[H][C@@](COC(=O)CCC=CCC=CCC=CCC=CCC=CCC=CCC)(COP(O)(=O)OCCN)OC(=O)CCCC=CCC=CCC=CCC=CCCCCC
Average Molecular Weight812.0661
Monoisotopic Molecular Weight811.515204861
Classification
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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID24769140
ChEMBL IDNot Available
KEGG Compound IDC00350
Pubchem Compound ID52924855
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB09696
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDLecithin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Phospholipase D2PLD2O14939
Phospholipase D3PLD3Q8IV08
Phospholipase D4PLD4Q96BZ4
Phosphatidylserine decarboxylase proenzymePISDQ9UG56
Phosphatidylethanolamine-binding protein 1PEBP1P30086
Phosphatidylethanolamine-binding protein 4PEBP4Q96S96
Abhydrolase domain-containing protein 4ABHD4Q8TB40
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference