Showing metabocard for PE(20:2(11Z,14Z)/P-18:1(9Z)) (BMDB0009315)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:40:07 UTC
Update Date2020-05-11 19:39:22 UTC
BMDB IDBMDB0009315
Secondary Accession Numbers
  • BMDB09315
Metabolite Identification
Common NamePE(20:2(11Z,14Z)/P-18:1(9Z))
DescriptionPE(20:2(11Z,14Z)/P-18:1(9Z)) 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(20:2(11Z,14Z)/P-18:1(9Z)), in particular, consists of one 11Z,14Z-eicosadienoyl chain to the C-1 atom, and one 1Z,9Z-octadecadienyl 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
GlycerophosphoethanolamineHMDB
1-(11Z,14Z-Eicosadienoyl)-2-(1Z,9Z-octadecadienyl)-sn-glycero-3-phosphoethanolamineHMDB
Glycerophosphoethanolamine(20:2(11Z,14Z)/p-18:1(9Z))HMDB
PE(20:3)HMDB
GPEtn(20:3)HMDB
Phophatidylethanolamine(20:3)HMDB
PE(20:2/P-18:1)HMDB
GPEtn(20:2/P-18:1)HMDB
Phophatidylethanolamine(20:2/p-18:1)HMDB
(2-Aminoethoxy)[(2R)-3-[(11Z,14Z)-icosa-11,14-dienoyloxy]-2-[(1Z,9Z)-octadeca-1,9-dien-1-yloxy]propoxy]phosphinateHMDB
Chemical FormulaC43H80NO7P
Average Molecular Weight754.0716
Monoisotopic Molecular Weight753.567240431
IUPAC Name(2-aminoethoxy)[(2R)-3-[(11Z,14Z)-icosa-11,14-dienoyloxy]-2-[(1Z,9Z)-octadeca-1,9-dien-1-yloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-3-[(11Z,14Z)-icosa-11,14-dienoyloxy]-2-[(1Z,9Z)-octadeca-1,9-dien-1-yloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCC\C=C/C\C=C/CCCCC)(COP(O)(=O)OCCN)O\C=C/CCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C43H80NO7P/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-36-43(45)49-40-42(41-51-52(46,47)50-39-37-44)48-38-35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h11,13,17-20,35,38,42H,3-10,12,14-16,21-34,36-37,39-41,44H2,1-2H3,(H,46,47)/b13-11-,19-17-,20-18-,38-35-/t42-/m1/s1
InChI KeyIBIDTCQKTHZZPM-ZTCNOODVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as glycerophosphoethanolamines. These are glycerolipids characterized by an ethanolamine ester of glycerophosphoric acid. 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoethanolamines
Direct ParentGlycerophosphoethanolamines
Alternative Parents
Substituents
  • Sn-glycero-3-phosphoethanolamine
  • Glycerol vinyl ether
  • Phosphoethanolamine
  • Fatty acid ester
  • Dialkyl phosphate
  • Fatty acyl
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Phosphoric acid ester
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Primary amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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
logP9.47ALOGPS
logP12.43ChemAxon
logS-7.1ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area117.31 ŲChemAxon
Rotatable Bond Count41ChemAxon
Refractivity222.3 m³·mol⁻¹ChemAxon
Polarizability93.01 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, Positivesplash10-0006-9020101200-bb9f8e3e509745929b3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9020002000-2500e115ca51437866b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9043013000-64433dcb5ea6518fc132View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pbi-2298210600-57df742c6004c10daf52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a73-9567200100-f1ac0fa15ea2ad8236fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9100000000-bdc252f9ee8984f61dffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-9200007800-4042f9a7696291e40307View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9300048300-6c33522f642fc537d988View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-4913100000-65838f49bc964a9b846bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ug0-4500000900-f2242846e41d752fd5bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002p-8933501200-a6e32fba482f524261d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9300000000-aa7cfe17dd5ac43f2377View 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 IDHMDB0009315
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53479741
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available