Showing metabocard for PE(P-18:1(11Z)/22:2(13Z,16Z)) (BMDB0011423)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:18:15 UTC
Update Date2020-05-11 19:52:10 UTC
BMDB IDBMDB0011423
Secondary Accession Numbers
  • BMDB11423
Metabolite Identification
Common NamePE(P-18:1(11Z)/22:2(13Z,16Z))
DescriptionPE(P-18:1(11Z)/22:2(13Z,16Z)) 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(P-18:1(11Z)/22:2(13Z,16Z)), in particular, consists of one 1Z,11Z-octadecadienyl chain to the C-1 atom, and one 13Z,16Z-docosadienoyl 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
1-(1-Enyl-vaccenoyl)-2-docosadienoyl-sn-glycero-3-phosphoethanolamineHMDB
(2-Aminoethoxy)[(2R)-2-[(13Z,16Z)-docosa-13,16-dienoyloxy]-3-[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]propoxy]phosphinateHMDB
1-(1Z,11Z-Octadecadienyl)-2-docosadienoyl-gpeHMDB
1-(1Z,11Z-Octadecadienyl)-2-docosadienoyl-sn-glycero-3-phosphoethanolamineHMDB
1-(1Z,11Z-Octadecadienyl)-2-docosadienoyl-sn-glycero-phosphatidylethanolamineHMDB
GPE(18:2/22:2)HMDB
GPE(40:4)HMDB
GPE(O-18:2(1Z,11Z)/22:2(13Z,16Z))HMDB
GPE(O-18:2(1Z,11Z)/22:2n6)HMDB
GPE(O-18:2(1Z,11Z)/22:2W6)HMDB
GPE(p-18:1(11Z)/22:2(13Z,16Z))HMDB
GPE(p-18:1(11Z)/22:2n6)HMDB
GPE(p-18:1(11Z)/22:2W6)HMDB
GPEtn(18:2/22:2)HMDB
GPEtn(40:4)HMDB
GPEtn(O-18:2(1Z,11Z)/22:2(13Z,16Z))HMDB
GPEtn(O-18:2(1Z,11Z)/22:2n6)HMDB
GPEtn(O-18:2(1Z,11Z)/22:2W6)HMDB
GPEtn(p-18:1(11Z)/22:2(13Z,16Z))HMDB
GPEtn(p-18:1(11Z)/22:2n6)HMDB
GPEtn(p-18:1(11Z)/22:2W6)HMDB
PE(18:2/22:2)HMDB
PE(40:4)HMDB
PE(O-18:2(1Z,11Z)/22:2(13Z,16Z))HMDB
PE(O-18:2(1Z,11Z)/22:2N6)HMDB
PE(O-18:2(1Z,11Z)/22:2W6)HMDB
PE(P-18:1(11Z)/22:2N6)HMDB
PE(P-18:1(11Z)/22:2W6)HMDB
Phosphatidylethanolamine(18:2/22:2)HMDB
Phosphatidylethanolamine(40:4)HMDB
Phosphatidylethanolamine(O-18:2(1Z,11Z)/22:2(13Z,16Z))HMDB
Phosphatidylethanolamine(O-18:2(1Z,11Z)/22:2n6)HMDB
Phosphatidylethanolamine(O-18:2(1Z,11Z)/22:2W6)HMDB
Phosphatidylethanolamine(p-18:1(11Z)/22:2(13Z,16Z))HMDB
Phosphatidylethanolamine(p-18:1(11Z)/22:2n6)HMDB
Phosphatidylethanolamine(p-18:1(11Z)/22:2W6)HMDB
Chemical FormulaC45H84NO7P
Average Molecular Weight782.1247
Monoisotopic Molecular Weight781.598540559
IUPAC Name(2-aminoethoxy)[(2R)-2-[(13Z,16Z)-docosa-13,16-dienoyloxy]-3-[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-2-[(13Z,16Z)-docosa-13,16-dienoyloxy]-3-[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](CO\C=C/CCCCCCCC\C=C/CCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C45H84NO7P/c1-3-5-7-9-11-13-15-17-19-21-22-23-24-26-28-30-32-34-36-38-45(47)53-44(43-52-54(48,49)51-41-39-46)42-50-40-37-35-33-31-29-27-25-20-18-16-14-12-10-8-6-4-2/h11,13-14,16-17,19,37,40,44H,3-10,12,15,18,20-36,38-39,41-43,46H2,1-2H3,(H,48,49)/b13-11-,16-14-,19-17-,40-37-/t44-/m1/s1
InChI KeyMYDAVUXDFNNDHX-XAGFNEJISA-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
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
logP9.71ALOGPS
logP13.31ChemAxon
logS-7.2ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area117.31 ŲChemAxon
Rotatable Bond Count43ChemAxon
Refractivity231.5 m³·mol⁻¹ChemAxon
Polarizability96.53 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-4200007900-709cf33983239a138d26View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-5100009200-f3b98eadcea618a73643View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-3923210000-c98af31d0217b074ce45View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2300000900-84e8fc9b52844566964cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-015c-3756910300-a5bd12ac963b17aae64dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002o-9803300000-b7855710b68191bc0596View 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 IDHMDB0011423
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028150
KNApSAcK IDNot Available
Chemspider ID24769307
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480883
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available