Showing metabocard for PE(20:5(5Z,8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)) (BMDB0009463)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:43:23 UTC
Update Date2020-05-11 19:41:25 UTC
BMDB IDBMDB0009463
Secondary Accession Numbers
  • BMDB09463
Metabolite Identification
Common NamePE(20:5(5Z,8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z))
DescriptionPE(20:5(5Z,8Z,11Z,14Z,17Z)/20:3(5Z,8Z,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(20:5(5Z,8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)), in particular, consists of one 5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl chain to the C-1 atom, and one 5Z,8Z,11Z-eicosatrienoyl 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
GPEtn(20:5/20:3)HMDB
GPEtn(40:8)HMDB
PE(20:5/20:3)HMDB
Phophatidylethanolamine(40:8)HMDB
1-Eicosapentaenoyl-2-meadoyl-sn-glycero-3-phosphoethanolamineHMDB
Phophatidylethanolamine(20:5/20:3)HMDB
1-(5Z,8Z,11Z,14Z,17Z-Eicosapentaenoyl)-2-(5Z,8Z,11Z-eicosatrienoyl)-sn-glycero-3-phosphoethanolamineHMDB
PE(40:8)HMDB
PE(20:5(5Z,8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z))Lipid Annotator
Chemical FormulaC45H74NO8P
Average Molecular Weight788.0447
Monoisotopic Molecular Weight787.515204861
IUPAC Name(2-aminoethoxy)[(2R)-3-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propoxy]phosphinic acid
Traditional NamePPP
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)(COP(O)(=O)OCCN)OC(=O)CCC\C=C/C\C=C/C\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C45H74NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-44(47)51-41-43(42-53-55(49,50)52-40-39-46)54-45(48)38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h5,7,11,13,17-20,23-26,29-32,43H,3-4,6,8-10,12,14-16,21-22,27-28,33-42,46H2,1-2H3,(H,49,50)/b7-5-,13-11-,19-17-,20-18-,25-23-,26-24-,31-29-,32-30-/t43-/m1/s1
InChI KeyXZCIYVSAHYFRHF-PJDWUMIWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phosphatidylethanolamines. These are glycerophosphoetahnolamines in which two fatty acids are bonded to the glycerol moiety through ester linkages.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoethanolamines
Direct ParentPhosphatidylethanolamines
Alternative Parents
Substituents
  • Diacylglycero-3-phosphoethanolamine
  • Phosphoethanolamine
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Primary amine
  • Carbonyl group
  • Organic oxide
  • 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
logP8.32ALOGPS
logP11.11ChemAxon
logS-7ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area134.38 ŲChemAxon
Rotatable Bond Count39ChemAxon
Refractivity236.74 m³·mol⁻¹ChemAxon
Polarizability91.3 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, Negativesplash10-000i-0003000900-b3840547a1b2b1f74557View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0003000900-b3840547a1b2b1f74557View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zg0-0109200300-ec0f2fe20f7cac1a4a6eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000001900-7ca2741b161e6cbdc279View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000b-0003339700-a6d09ff8523a8b3cd379View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0003339300-44a022078d8e06170f46View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000001090-e0f6f8fa5cba62868f74View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03xr-0000002290-81a80eb281fd71390d5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0100301910-4923039474b0c973d67dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000001900-c84cbff1d94824fa08f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000b-0003339700-b5d27b09b367805756bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0003339300-8893944aec2997a2eda7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0003000900-cc4072b974ca8a827d34View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0003000900-cc4072b974ca8a827d34View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zg0-0109200300-66d6e587658b857de503View 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 IDHMDB0009463
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB026653
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53479833
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available