Showing metabocard for PE(O-18:1(1Z)/20:4(5Z,8Z,11Z,14Z)) (BMDB0005779)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:18:25 UTC
Update Date2020-05-11 20:41:21 UTC
BMDB IDBMDB0005779
Secondary Accession Numbers
  • BMDB05779
Metabolite Identification
Common NamePE(O-18:1(1Z)/20:4(5Z,8Z,11Z,14Z))
DescriptionPE(P-18:0/20:4(5Z,8Z,11Z,14Z)) 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(P-18:0/20:4(5Z,8Z,11Z,14Z)), in particular, consists of one 1Z-octadecenyl chain to the C-1 atom, and one 5Z,8Z,11Z,14Z-eicosatetraenoyl 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-(1Z-Octadecenyl)-2-(5Z,8Z,11Z,14Z- eicosatetraenoyl)-sn-glycero-3-phosphoethanolamineChEBI
1-(1Z-Octadecenyl)-2-(5Z,8Z,11Z,14Z-icosatetraenoyl)-sn-glycero-3-phosphoethanolamine zwitterionChEBI
1-(1-Enyl-stearoyl)-2-arachidonoyl-sn-glycero-3-phosphoethanolamineHMDB
1-(1Z-Octadecenyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamineHMDB
1-Alkenyl-2-acyl-glycerophosphoethanolamineHMDB
GPE(O-18:1(1Z)/20:4(5Z,8Z,11Z,14Z))HMDB
GPE(O-18:1(1Z)/20:4)HMDB
GPE(O-18:1(1Z)/20:4n6)HMDB
GPE(O-18:1(1Z)/20:4W6)HMDB
GPE(p-18:0/20:4(5Z,8Z,11Z,14Z))HMDB
GPE(p-18:0/20:4n6)HMDB
GPE(p-18:0/20:4W6)HMDB
GPEtn(38:5)HMDB
GPEtn(O-18:1(1Z)/20:4(5Z,8Z,11Z,14Z))HMDB
GPEtn(O-18:1(1Z)/20:4)HMDB
GPEtn(O-18:1(1Z)/20:4n6)HMDB
GPEtn(O-18:1(1Z)/20:4W6)HMDB
GPEtn(p-18:0/20:4(5Z,8Z,11Z,14Z))HMDB
GPEtn(p-18:0/20:4)HMDB
GPEtn(p-18:0/20:4n6)HMDB
GPEtn(p-18:0/20:4W6)HMDB
PE(38:5)HMDB
PE(O-18:1(1Z)/20:4(5Z,8Z,11Z,14Z))HMDB
PE(O-18:1(1Z)/20:4)HMDB
PE(O-18:1(1Z)/20:4N6)HMDB
PE(O-18:1(1Z)/20:4W6)HMDB
PE(P-18:0/20:4)HMDB
PE(P-18:0/20:4N6)HMDB
PE(P-18:0/20:4W6)HMDB
Phophatidylethanolamine(38:5)HMDB
Phophatidylethanolamine(O-18:1(1Z)/20:4(5Z,8Z,11Z,14Z))HMDB
Phophatidylethanolamine(O-18:1(1Z)/20:4)HMDB
Phophatidylethanolamine(O-18:1(1Z)/20:4n6)HMDB
Phophatidylethanolamine(O-18:1(1Z)/20:4W6)HMDB
Phophatidylethanolamine(p-18:0/20:4(5Z,8Z,11Z,14Z))HMDB
Phophatidylethanolamine(p-18:0/20:4)HMDB
Phophatidylethanolamine(p-18:0/20:4n6)HMDB
Phophatidylethanolamine(p-18:0/20:4W6)HMDB
GPE(38:5)HMDB
PE(P-18:0/20:4(5Z,8Z,11Z,14Z))HMDB
Chemical FormulaC43H78NO7P
Average Molecular Weight752.0557
Monoisotopic Molecular Weight751.551590367
IUPAC Name(2-aminoethoxy)[(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-[(1Z)-octadec-1-en-1-yloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy((2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-[(1Z)-octadec-1-en-1-yloxy]propoxy)phosphinic acid
CAS Registry Number103597-60-0
SMILES
[H][C@@](CO\C=C/CCCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C43H78NO7P/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-36-43(45)51-42(41-50-52(46,47)49-39-37-44)40-48-38-35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h11,13,17,19,22,24,28,30,35,38,42H,3-10,12,14-16,18,20-21,23,25-27,29,31-34,36-37,39-41,44H2,1-2H3,(H,46,47)/b13-11-,19-17-,24-22-,30-28-,38-35-/t42-/m1/s1
InChI KeyURPXXNCTXCOATD-FXMFQVEGSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-(1z-alkenyl),2-acylglycerophosphoethanolamines. These are glycerophosphoethanolamines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one 1Z-alkenyl chain attached through an ether linkage at the O1-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoethanolamines
Direct Parent1-(1Z-alkenyl),2-acylglycerophosphoethanolamines
Alternative Parents
Substituents
  • 1-(1z-alkenyl),2-acylglycerophosphoethanolamine
  • Glycerol vinyl ether
  • Phosphoethanolamine
  • Fatty acid ester
  • Dialkyl phosphate
  • Fatty acyl
  • Alkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary amine
  • Primary aliphatic amine
  • Organic oxygen compound
  • Amine
  • Carbonyl group
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
  • 1-(alk-1-enyl)-2-acyl-sn-glycero-3-phosphoethanolamine (CHEBI:79207 )
  • 1-(1Z-alkenyl),2-acylglycerophosphoethanolamines (LMGP02030003 )
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
logP9.4ALOGPS
logP12.06ChemAxon
logS-7.1ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area117.31 ŲChemAxon
Rotatable Bond Count40ChemAxon
Refractivity223.41 m³·mol⁻¹ChemAxon
Polarizability90.28 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, Positivesplash10-0006-9021101200-09deeefa2d4acc25b467View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9031001000-4eab33bf274405f87152View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9053002000-3bd90e2a302a4ac60777View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3375600900-3567dfd8fb570a78d29dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9551300100-48d9fed485f0b8163864View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9100000000-56001c4ee49886d1ba03View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-3000006900-5408a4cb69aa5ad7df27View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0c03-7100039200-d776b540c3b61929b485View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-3932310000-1606a2bb4e452e445561View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3300000900-c521f75762a51af60f3bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udm-4631900300-7e505f4bd4a4fc79948eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f96-9712200000-e8cc9485e88ebbe382d9View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Brain
  • Placenta
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
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0005779
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023768
KNApSAcK IDNot Available
Chemspider ID7826008
KEGG Compound IDC00350
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6548
PubChem Compound9547058
PDB IDNot Available
ChEBI ID78342
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available