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Showing Compound PE(22:0/22:0) (FDB026691)

Record Information
Version1.0
Creation date2011-09-21 01:14:09 UTC
Update date2020-04-06 23:43:36 UTC
Primary IDFDB026691
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePE(22:0/22:0)
DescriptionPE(22:0/22:0) 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(22:0/22:0), in particular, consists of two chains of behenic acid at the C-1 and C-2 positions. The behenic acid moieties are derived from groundnut oil. 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
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Phophatidylethanolamine(44:0)HMDB
1,2-Dibehenoyl-rac-glycero-3-phosphoethanolamineHMDB
PE(44:0)HMDB
GPEtn(44:0)HMDB
Phophatidylethanolamine(22:0/22:0)HMDB
1,2-Didocosanoyl-rac-glycero-3-phosphoethanolamineHMDB
GPEtn(22:0/22:0)HMDB
PE(22:0/22:0)Lipid Annotator
1,2-Dibehenoyl-rac-glycero-3-oethanolamineHMDB
1,2-dibehenoyl-rac-glycero-3-phosphoethanolaminehmdb
Predicted Properties
PropertyValueSource
Water Solubility3.7e-05 g/LALOGPS
logP9.72ALOGPS
logP15.79ChemAxon
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 Count51ChemAxon
Refractivity246.22 m³·mol⁻¹ChemAxon
Polarizability111.24 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC49H98NO8P
IUPAC name(2-aminoethoxy)[(2R)-2,3-bis(docosanoyloxy)propoxy]phosphinic acid
InChI IdentifierInChI=1S/C49H98NO8P/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/h47H,3-46,50H2,1-2H3,(H,53,54)/t47-/m1/s1
InChI KeyTZFNCLDMKUFURD-QZNUWAOFSA-N
Isomeric SMILES[H][C@@](COC(=O)CCCCCCCCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCCCCCCCCCC
Average Molecular Weight860.2781
Monoisotopic Molecular Weight859.703005629
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 Descriptors
Ontology
Physiological effect

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0001000090-766e0e9dddbaafdc83412017-10-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0001000090-766e0e9dddbaafdc83412017-10-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052r-0309030060-806dd95d39920109a9022017-10-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000190-addb6e018e1b5df881ee2017-10-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02t9-0001030970-0fab841f2dab392fed852017-10-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0001030930-fd11a49d9e432b4808592017-10-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000190-0c46c36afa57013d98a12021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000000190-383c77aa0c34fa77cddc2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0100100190-dc7115d746b9d4b229212021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000190-e203f7104b20ec2c84ff2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02t9-0001030970-2f11b46b8028ae2f83a12021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0001030930-8412dbb5f836260f0cc52021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0001000090-309d87b03eb266297b572021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0001000090-309d87b03eb266297b572021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052r-0309030060-fe0a9d1892a4b35005da2021-09-24View Spectrum
NMRNot Available
ChemSpider ID7825817
ChEMBL IDNot Available
KEGG Compound IDC00350
Pubchem Compound ID9546867
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB09501
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