Showing metabocard for PE(18:3(6Z,9Z,12Z)/P-18:0) (BMDB0009148)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:36:42 UTC
Update Date2020-05-11 19:37:03 UTC
BMDB IDBMDB0009148
Secondary Accession Numbers
  • BMDB09148
Metabolite Identification
Common NamePE(18:3(6Z,9Z,12Z)/P-18:0)
DescriptionPE(18:3(6Z,9Z,12Z)/P-18:0) 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(18:3(6Z,9Z,12Z)/P-18:0), in particular, consists of one 6Z,9Z,12Z-octadecatrienoyl chain to the C-1 atom, and one 1Z-octadecenyl 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-g-Linolenoyl-2-(1-enyl-stearoyl)-sn-glycero-3-phosphoethanolamineHMDB
1-gamma-Linolenoyl-2-(1-enyl-stearoyl)-sn-glycero-3-phosphoethanolamineHMDB
GPEtn(18:3/18:0)HMDB
GPEtn(18:3n6/18:0)HMDB
GPEtn(18:3W6/18:0)HMDB
GPEtn(36:3)HMDB
PE(18:3/18:0)HMDB
PE(18:3N6/18:0)HMDB
PE(18:3W6/18:0)HMDB
PE(36:3)HMDB
Phophatidylethanolamine(18:3/18:0)HMDB
Phophatidylethanolamine(18:3n6/18:0)HMDB
Phophatidylethanolamine(18:3W6/18:0)HMDB
Phophatidylethanolamine(36:3)HMDB
(2-Aminoethoxy)[(2R)-2-[(1Z)-octadec-1-en-1-yloxy]-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxy]phosphinateHMDB
Chemical FormulaC41H76NO7P
Average Molecular Weight726.0184
Monoisotopic Molecular Weight725.535940303
IUPAC Name(2-aminoethoxy)[(2R)-2-[(1Z)-octadec-1-en-1-yloxy]-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-2-[(1Z)-octadec-1-en-1-yloxy]-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC)(COP(O)(=O)OCCN)O\C=C/CCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C41H76NO7P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-36-46-40(39-49-50(44,45)48-37-35-42)38-47-41(43)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h12,14,18,20,24,26,33,36,40H,3-11,13,15-17,19,21-23,25,27-32,34-35,37-39,42H2,1-2H3,(H,44,45)/b14-12-,20-18-,26-24-,36-33-/t40-/m1/s1
InChI KeySYCLSGAGTPLKOH-GMDHOFCPSA-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
logP9.26ALOGPS
logP11.54ChemAxon
logS-7ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area117.31 ŲChemAxon
Rotatable Bond Count39ChemAxon
Refractivity213.1 m³·mol⁻¹ChemAxon
Polarizability89.14 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, Positivesplash10-0006-9030110200-ea9ca7ab74a6bd96208bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9030001000-948d23b2dfc1812d2d8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9062011000-132cd5f08d1cff9fcda3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05i0-1190201200-44213341b5137cc6b901View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-5390100000-3923b57d670f96a2cfcaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9110000000-b60321d0f4455a14ab18View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00g0-5600001900-07f59416d5307099764dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004v-9733510200-aa21759af5aaaf29e8d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9300000000-97178ba694d7110e2d3cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-6300035900-e09b1991ef67bb71d0c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-9200065000-0369f8f5d45ebfa007faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-3931200000-a105294173d5d9cea1c4View 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 IDHMDB0009148
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB026338
KNApSAcK IDNot Available
Chemspider ID24768611
KEGG Compound IDC00350
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53479682
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available