Showing metabocard for PE(18:3(6Z,9Z,12Z)/P-16:0) (BMDB0009147)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:36:41 UTC
Update Date2020-05-11 19:37:02 UTC
BMDB IDBMDB0009147
Secondary Accession Numbers
  • BMDB09147
Metabolite Identification
Common NamePE(18:3(6Z,9Z,12Z)/P-16:0)
DescriptionPE(18:3(6Z,9Z,12Z)/P-16:0) 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-16:0), in particular, consists of one 6Z,9Z,12Z-octadecatrienoyl chain to the C-1 atom, and one 1Z-hexadecenyl 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-(6Z,9Z,12Z-Octadecatrienoyl)-2-(1Z-hexadecenyl)-sn-glycero-3-phosphoethanolamineHMDB
Glycerophosphoethanolamine(18:3(6Z,9Z,12Z)/p-16:0)HMDB
PE(18:3)HMDB
GPEtn(18:3)HMDB
Phophatidylethanolamine(18:3)HMDB
PE(18:3/P-16:0)HMDB
GPEtn(18:3/P-16:0)HMDB
Phophatidylethanolamine(18:3/p-16:0)HMDB
(2-Aminoethoxy)[(2R)-2-[(1Z)-hexadec-1-en-1-yloxy]-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxy]phosphinateHMDB
Chemical FormulaC39H72NO7P
Average Molecular Weight697.9652
Monoisotopic Molecular Weight697.504640175
IUPAC Name(2-aminoethoxy)[(2R)-2-[(1Z)-hexadec-1-en-1-yloxy]-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-2-[(1Z)-hexadec-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/CCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C39H72NO7P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-39(41)45-36-38(37-47-48(42,43)46-35-33-40)44-34-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h11,13,17,19,22,24,31,34,38H,3-10,12,14-16,18,20-21,23,25-30,32-33,35-37,40H2,1-2H3,(H,42,43)/b13-11-,19-17-,24-22-,34-31-/t38-/m1/s1
InChI KeyHIBHCGGDRIJXQH-KDBKAMDRSA-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
logP8.87ALOGPS
logP10.65ChemAxon
logS-6.9ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area117.31 ŲChemAxon
Rotatable Bond Count37ChemAxon
Refractivity203.89 m³·mol⁻¹ChemAxon
Polarizability84.83 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, Positivesplash10-0lz9-6850609000-1357c5866915c68f1507View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9020112000-8475b94d106f69301912View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9030001000-df55678b4ece9a627e36View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9070021000-b5fb7be910f91dd8a46eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-056s-1190204000-0523aa07591c0d6ed6c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-5390101000-332edde637b12a875434View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9110000000-b2e3c76cf2e4cc1376adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-4100039000-dadf82a4f81d154a8f54View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-7200092000-670aa64738f70f779a4aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-3941100000-b6a62cb5dbc3ac9864e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000b-4500009000-d4528eddca7bb9236314View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004m-9733413000-45de3ddd5abdbe42d935View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9300000000-97178ba694d7110e2d3cView 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 IDHMDB0009147
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB026337
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53479681
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available