Record Information
Version1.0
Creation date2011-09-21 01:06:58 UTC
Update date2020-04-06 23:43:35 UTC
Primary IDFDB026181
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePE(18:0/18:0)
DescriptionPE(18:0/18:0) 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 positions. PE(18:0/18:0), in particular, consists of two octadecanoyl chains at positions C-1 and C-2. 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.
CAS Number1069-79-0
Structure
Thumb
Synonyms
SynonymSource
2-Ammonioethyl (2R)-2,3-bis(stearoyloxy)propyl phosphateChEBI
2-Ammonioethyl (2R)-2,3-bis(stearoyloxy)propyl phosphoric acidGenerator
1,2-Distearoylphosphatidylethanolamine, (R)-isomerHMDB
DC18PEHMDB
Distearoyl-L-phosphatidylethanolamineHMDB
1,2-Dioctadecanoyl-sn-glycero-3-phosphoethanolamineHMDB
1,2-Distearoylphosphatidylethanolamine, (S)-isomerHMDB
1,2-DistearoylphosphatidylethanolamineHMDB
1,2-Distearoylphosphatidylethanolamine, (+-)-isomerHMDB
DSPEHMDB
GPEtn(18:0/18:0)HMDB
PE(36:0)HMDB
Phophatidylethanolamine(36:0)HMDB
Phophatidylethanolamine(18:0/18:0)HMDB
GPEtn(36:0)HMDB
1,2-Dioctadecanoyl-rac-glycero-3-phosphoethanolamineHMDB
1,2-Distearoyl-rac-glycero-3-phosphoethanolamineHMDB
PE(18:0/18:0)Lipid Annotator
1,2-Distearoyl-rac-glycero-3-oethanolamineHMDB
1,2-distearoyl-rac-glycero-3-phosphoethanolaminehmdb
2-Ammonioethyl (2R)-2,3-bis(stearoyloxy)propyl ateChEBI
2-Ammonioethyl (2R)-2,3-bis(stearoyloxy)propyl ic acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility5.4e-05 g/LALOGPS
logP8.91ALOGPS
logP12.23ChemAxon
logS-7.1ALOGPS
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
Refractivity209.41 m³·mol⁻¹ChemAxon
Polarizability93.58 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC41H82NO8P
IUPAC name(2-aminoethoxy)[(2R)-2,3-bis(octadecanoyloxy)propoxy]phosphinic acid
InChI IdentifierInChI=1S/C41H82NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-40(43)47-37-39(38-49-51(45,46)48-36-35-42)50-41(44)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h39H,3-38,42H2,1-2H3,(H,45,46)/t39-/m1/s1
InChI KeyLVNGJLRDBYCPGB-LDLOPFEMSA-N
Isomeric SMILES[H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCCCCCC
Average Molecular Weight748.08
Monoisotopic Molecular Weight747.577805602
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-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPE(18:0/18:0), non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - IT 40V, negativesplash10-000t-0050400900-6cd50eaec4c5bd9cc4e1Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-001i-0090000000-2b7039a920928ec43b6bSpectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-001i-0090000000-d1c88edcedefe16702cbSpectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-001i-0090000000-ad7ef028ba66af27d4c3Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-001i-0090000000-562c4cef385ea8ac8ca6Spectrum
MS/MSLC-MS/MS Spectrum - IT 30V, positivesplash10-0a4j-0000009600-48255e2ef051be7e84ddSpectrum
MS/MSLC-MS/MS Spectrum - n/a 52V, positivesplash10-0a4i-0000009000-6eb6cd259aab68421309Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0010000900-60329d5a7c12551bbc42Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0010000900-60329d5a7c12551bbc42Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001j-0390300600-067b245407347d117669Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0010000900-6bd6d72f410de62ad700Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0010000900-6bd6d72f410de62ad700Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001j-0390300600-96208b51ba43ac55e684Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000001900-4a7b6d9013d36f909f90Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-0001309700-eeada937f3ad0f7968a8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0001309300-f72f58cbd9cb16b1f4d2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000001900-50a418c4f44c815f6289Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fr-0000001900-34619ad7f9118f8f3038Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0100101900-6718aff73f7bb076a558Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000001900-bbbbfd5d071fd445575fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-0001309700-96819fbf9850a4df1ffeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0001309300-60566be72def6d31ad0dSpectrum
NMRNot Available
ChemSpider ID394271
ChEMBL IDNot Available
KEGG Compound IDC00350
Pubchem Compound ID447078
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB08991
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET ID3PE
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