Showing metabocard for PE(22:1(13Z)/P-18:1(11Z)) (BMDB0009545)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:45:06 UTC
Update Date2020-05-11 19:42:33 UTC
BMDB IDBMDB0009545
Secondary Accession Numbers
  • BMDB09545
Metabolite Identification
Common NamePE(22:1(13Z)/P-18:1(11Z))
DescriptionPE(22:1(13Z)/P-18:1(11Z)) 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(22:1(13Z)/P-18:1(11Z)), in particular, consists of one 13Z-docosenoyl chain to the C-1 atom, and one 1Z,11Z-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-(13Z-Docosenoyl)-2-(1Z,11Z-octadecadienyl)-sn-glycero-3-phosphoethanolamineHMDB
Glycerophosphoethanolamine(22:1(13Z)/p-18:1(11Z))HMDB
PE(22:2)HMDB
GPEtn(22:2)HMDB
Phophatidylethanolamine(22:2)HMDB
PE(22:1/P-18:1)HMDB
GPEtn(22:1/P-18:1)HMDB
Phophatidylethanolamine(22:1/p-18:1)HMDB
(2-Aminoethoxy)[(2R)-3-[(13Z)-docos-13-enoyloxy]-2-[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]propoxy]phosphinateHMDB
Chemical FormulaC45H86NO7P
Average Molecular Weight784.1406
Monoisotopic Molecular Weight783.614190623
IUPAC Name(2-aminoethoxy)[(2R)-3-[(13Z)-docos-13-enoyloxy]-2-[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-3-[(13Z)-docos-13-enoyloxy]-2-[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCCC\C=C/CCCCCCCC)(COP(O)(=O)OCCN)O\C=C/CCCCCCCC\C=C/CCCCCC
InChI Identifier
InChI=1S/C45H86NO7P/c1-3-5-7-9-11-13-15-17-19-21-22-23-24-26-28-30-32-34-36-38-45(47)51-42-44(43-53-54(48,49)52-41-39-46)50-40-37-35-33-31-29-27-25-20-18-16-14-12-10-8-6-4-2/h14,16-17,19,37,40,44H,3-13,15,18,20-36,38-39,41-43,46H2,1-2H3,(H,48,49)/b16-14-,19-17-,40-37-/t44-/m1/s1
InChI KeyQNAFMLUXQLBFIC-YLDKWXJFSA-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
logP9.76ALOGPS
logP13.68ChemAxon
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 Count44ChemAxon
Refractivity230.38 m³·mol⁻¹ChemAxon
Polarizability98.8 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, Positivesplash10-0006-9002101200-bcdd0802a77f27e70d12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9012001100-348030c40420a5b80226View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9033004100-7e1a3bc663aaa269908eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00li-1129110500-c43bd8d7345c25b12cb9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00n3-6419100100-11b5ff02fbe4777b3cb5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9201000000-1c2bc706ba1f61e8c2cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001l-5300005900-5dc5aa2aceb85e03c7c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9200028500-c33f893aecfa0787bc36View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-5904100000-d76584a294d8b4dc7b2aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0040-4500000900-4132eda8840eec95aed0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9833221300-48ba75b117fd9ff13e00View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9300000000-e979870ee41b43027413View 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 IDHMDB0009545
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 Compound53479883
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available