Showing metabocard for PE(24:0/P-18:1(11Z)) (BMDB0009743)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:49:22 UTC
Update Date2020-05-11 19:45:18 UTC
BMDB IDBMDB0009743
Secondary Accession Numbers
  • BMDB09743
Metabolite Identification
Common NamePE(24:0/P-18:1(11Z))
DescriptionPE(24:0/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(24:0/P-18:1(11Z)), in particular, consists of one tetracosanoyl 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
GlycerophosphoethanolamineMetBuilder, HMDB
1-Tetracosanoyl-2-(1Z,11Z-octadecadienyl)-sn-glycero-3-phosphoethanolamineMetBuilder, HMDB
Glycerophosphoethanolamine(24:0/p-18:1(11Z))MetBuilder, HMDB
PE(24:1)MetBuilder, HMDB
GPEtn(24:1)MetBuilder, HMDB
Phophatidylethanolamine(24:1)MetBuilder, HMDB
PE(24:0/P-18:1)MetBuilder, HMDB
GPEtn(24:0/P-18:1)MetBuilder, HMDB
Phophatidylethanolamine(24:0/p-18:1)MetBuilder, HMDB
(2-Aminoethoxy)[(2R)-2-[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]-3-(tetracosanoyloxy)propoxy]phosphinateGenerator, HMDB
Chemical FormulaC47H92NO7P
Average Molecular Weight814.2096
Monoisotopic Molecular Weight813.661140815
IUPAC Name(2-aminoethoxy)[(2R)-2-[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]-3-(tetracosanoyloxy)propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-2-[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]-3-(tetracosanoyloxy)propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)O\C=C/CCCCCCCC\C=C/CCCCCC
InChI Identifier
InChI=1S/C47H92NO7P/c1-3-5-7-9-11-13-15-17-19-21-22-23-24-25-26-28-30-32-34-36-38-40-47(49)53-44-46(45-55-56(50,51)54-43-41-48)52-42-39-37-35-33-31-29-27-20-18-16-14-12-10-8-6-4-2/h14,16,39,42,46H,3-13,15,17-38,40-41,43-45,48H2,1-2H3,(H,50,51)/b16-14-,42-39-/t46-/m1/s1
InChI KeyPUVBEVMEGFFJNG-RWLNHGTRSA-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
logP9.94ALOGPS
logP14.93ChemAxon
logS-7.3ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area117.31 ŲChemAxon
Rotatable Bond Count47ChemAxon
Refractivity238.47 m³·mol⁻¹ChemAxon
Polarizability104.79 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, Positivesplash10-0006-9002101010-b8daed4b4d9fd4974819View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9002000100-21e344bf254617530a92View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9014003100-d18fa3872d8425844ebeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02ta-1119110220-662b2d412655d8837253View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016v-6309100000-c45ee45376d2986edefeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9101000000-77a7bfeb1f754f42d640View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-3100003290-aee746a2709777ed14d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9200017400-4338713cd1147948e22eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-5913220000-1b41d85eae81da41420fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03g0-5600000190-28eb1801058feb54e66dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02bg-9831111030-4c8542b8c87d8bba0206View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9300000000-d6f812323dfca6799482View 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 IDHMDB0009743
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24769183
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480015
PDB IDNot Available
ChEBI ID172834
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available