Phosphatidylethanolamine (CHEM025892)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 22:39:57 UTC
Update Date2016-11-09 01:18:10 UTC
Accession NumberCHEM025892
Identification
Common NamePhosphatidylethanolamine
ClassSmall Molecule
DescriptionPE(P-18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)) belongs to the class of organic compounds known as 1-(1z-alkenyl),2-acylglycerophosphoethanolamines. These are glycerophosphoethanolamines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one 1Z-alkenyl chain attached through an ether linkage at the O1-position. PE(P-18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)) is possibly soluble (in water) and a very strong basic compound (based on its pKa).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2-Aminoethoxy)[(2R)-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]-3-[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]propoxy]phosphinateHMDB
1-(1Z,11Z-Octadecadienyl)-2-eicosapentaenoyl-gpeHMDB
1-(1Z,11Z-Octadecadienyl)-2-eicosapentaenoyl-sn-glycero-3-phosphoethanolamineHMDB
1-(1Z,11Z-Octadecadienyl)-2-eicosapentaenoyl-sn-glycero-phosphatidylethanolamineHMDB
GPE(18:2/20:5)HMDB
GPE(38:7)HMDB
GPE(O-18:2(1Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))HMDB
GPE(O-18:2(1Z,11Z)/20:5n3)HMDB
GPE(O-18:2(1Z,11Z)/20:5W3)HMDB
GPE(p-18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))HMDB
GPE(p-18:1(11Z)/20:5n3)HMDB
GPE(p-18:1(11Z)/20:5W3)HMDB
GPEtn(18:2/20:5)HMDB
GPEtn(38:7)HMDB
GPEtn(O-18:2(1Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))HMDB
GPEtn(O-18:2(1Z,11Z)/20:5n3)HMDB
GPEtn(O-18:2(1Z,11Z)/20:5W3)HMDB
GPEtn(p-18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))HMDB
GPEtn(p-18:1(11Z)/20:5n3)HMDB
GPEtn(p-18:1(11Z)/20:5W3)HMDB
PE(18:2/20:5)HMDB
PE(38:7)HMDB
PE(O-18:2(1Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))HMDB
PE(O-18:2(1Z,11Z)/20:5N3)HMDB
PE(O-18:2(1Z,11Z)/20:5W3)HMDB
PE(P-18:1(11Z)/20:5N3)HMDB
PE(P-18:1(11Z)/20:5W3)HMDB
Phosphatidylethanolamine(18:2/20:5)HMDB
Phosphatidylethanolamine(38:7)HMDB
Phosphatidylethanolamine(O-18:2(1Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))HMDB
Phosphatidylethanolamine(O-18:2(1Z,11Z)/20:5n3)HMDB
Phosphatidylethanolamine(O-18:2(1Z,11Z)/20:5W3)HMDB
Phosphatidylethanolamine(p-18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))HMDB
Phosphatidylethanolamine(p-18:1(11Z)/20:5n3)HMDB
Phosphatidylethanolamine(p-18:1(11Z)/20:5W3)HMDB
Chemical FormulaC43H74NO7P
Average Molecular Mass748.024 g/mol
Monoisotopic Mass747.520 g/mol
CAS Registry NumberNot Available
IUPAC Name(2-aminoethoxy)[(2R)-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]-3-[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]-3-[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]propoxyphosphinic acid
SMILES[H][C@@](CO\C=C/CCCCCCCC\C=C/CCCCCC)(COP(O)(=O)OCCN)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
InChI IdentifierInChI=1S/C43H74NO7P/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-36-43(45)51-42(41-50-52(46,47)49-39-37-44)40-48-38-35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h5,7,11,13-14,16-17,19,22,24,28,30,35,38,42H,3-4,6,8-10,12,15,18,20-21,23,25-27,29,31-34,36-37,39-41,44H2,1-2H3,(H,46,47)/b7-5-,13-11-,16-14-,19-17-,24-22-,30-28-,38-35-/t42-/m1/s1
InChI KeyRDLRIZLZWSNORN-FSOAWXQVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-(1z-alkenyl),2-acylglycerophosphoethanolamines. These are glycerophosphoethanolamines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one 1Z-alkenyl chain attached through an ether linkage at the O1-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoethanolamines
Direct Parent1-(1Z-alkenyl),2-acylglycerophosphoethanolamines
Alternative Parents
Substituents
  • 1-(1z-alkenyl),2-acylglycerophosphoethanolamine
  • Glycerol vinyl ether
  • Phosphoethanolamine
  • Fatty acid ester
  • Dialkyl phosphate
  • Fatty acyl
  • Alkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary amine
  • Primary aliphatic amine
  • Organic oxygen compound
  • Amine
  • Carbonyl group
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.1e-05 g/LALOGPS
logP8.97ALOGPS
logP11.34ChemAxon
logS-7ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area117.31 ŲChemAxon
Rotatable Bond Count38ChemAxon
Refractivity225.65 m³·mol⁻¹ChemAxon
Polarizability87.99 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9021100200-7ac23768785e8ae5ab11Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9021001000-528865017f3115ad299dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9054011000-5dc5a3edbe57b6fa9fb4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udm-2384701900-0845fc49fbfde05c89e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9661300100-03bc9e9b753e82101031Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9110000000-bc94ff42a3537e49f3e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-3300000900-7ae0dd7d06ff567a2ef9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00l5-4791800300-fb28d1d1d5a62db7f2ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-7911100000-adf716e5ab92330ea23fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-3000007900-d5a619ba6988cb546ee9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-5000019200-fdc092b14ceb5fa4e27bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-3962211000-88b96f3742975ef6559fSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0011420
FooDB IDFDB005556
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID24769304
ChEBI IDNot Available
PubChem Compound ID53480880
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Bitman J, Wood DL: Changes in milk fat phospholipids during lactation. J Dairy Sci. 1990 May;73(5):1208-16. doi: 10.3168/jds.S0022-0302(90)78784-X.
2. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78.
3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
4. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
5. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
6. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
7. Phospholipids Handbook
8. The lipid handbook with CD-ROM