Showing metabocard for PE(P-18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (BMDB0011420)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:18:11 UTC
Update Date2020-06-04 20:50:31 UTC
BMDB IDBMDB0011420
Secondary Accession Numbers
  • BMDB11420
Metabolite Identification
Common NamePE(P-18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))
DescriptionPE(P-18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 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-18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)), in particular, consists of one 1Z,11Z-octadecadienyl chain to the C-1 atom, and one 5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl 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
(2-Aminoethoxy)[(2R)-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]-3-[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]propoxy]phosphinateHMDB
1-(1Z,11Z-Octadecadienyl)-2-eicosapentaenoyl-gpeHMDB
1-(1Z,11Z-Octadecadienyl)-2-eicosapentaenoyl-sn-glycero-3-phosphoethanolamineHMDB
1-(1Z,11Z-Octadecadienyl)-2-eicosapentaenoyl-sn-glycero-phosphatidylethanolamineHMDB
GPE(18:2/20:5)HMDB
GPE(38:7)HMDB
GPE(O-18:2(1Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))HMDB
GPE(O-18:2(1Z,11Z)/20:5n3)HMDB
GPE(O-18:2(1Z,11Z)/20:5W3)HMDB
GPE(p-18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))HMDB
GPE(p-18:1(11Z)/20:5n3)HMDB
GPE(p-18:1(11Z)/20:5W3)HMDB
GPEtn(18:2/20:5)HMDB
GPEtn(38:7)HMDB
GPEtn(O-18:2(1Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))HMDB
GPEtn(O-18:2(1Z,11Z)/20:5n3)HMDB
GPEtn(O-18:2(1Z,11Z)/20:5W3)HMDB
GPEtn(p-18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))HMDB
GPEtn(p-18:1(11Z)/20:5n3)HMDB
GPEtn(p-18:1(11Z)/20:5W3)HMDB
PE(18:2/20:5)HMDB
PE(38:7)HMDB
PE(O-18:2(1Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))HMDB
PE(O-18:2(1Z,11Z)/20:5N3)HMDB
PE(O-18:2(1Z,11Z)/20:5W3)HMDB
PE(P-18:1(11Z)/20:5N3)HMDB
PE(P-18:1(11Z)/20:5W3)HMDB
Phosphatidylethanolamine(18:2/20:5)HMDB
Phosphatidylethanolamine(38:7)HMDB
Phosphatidylethanolamine(O-18:2(1Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))HMDB
Phosphatidylethanolamine(O-18:2(1Z,11Z)/20:5n3)HMDB
Phosphatidylethanolamine(O-18:2(1Z,11Z)/20:5W3)HMDB
Phosphatidylethanolamine(p-18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))HMDB
Phosphatidylethanolamine(p-18:1(11Z)/20:5n3)HMDB
Phosphatidylethanolamine(p-18:1(11Z)/20:5W3)HMDB
Chemical FormulaC43H74NO7P
Average Molecular Weight748.0239
Monoisotopic Molecular Weight747.520290239
IUPAC Name(2-aminoethoxy)[(2R)-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]-3-[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]-3-[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](CO\C=C/CCCCCCCC\C=C/CCCCCC)(COP(O)(=O)OCCN)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C43H74NO7P/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/h5,7,11,13-14,16-17,19,22,24,28,30,35,38,42H,3-4,6,8-10,12,15,18,20-21,23,25-27,29,31-34,36-37,39-41,44H2,1-2H3,(H,46,47)/b7-5-,13-11-,16-14-,19-17-,24-22-,30-28-,38-35-/t42-/m1/s1
InChI KeyRDLRIZLZWSNORN-FSOAWXQVSA-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 DescriptorsNot Available
Ontology
StatusDetected and 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
logP8.97ALOGPS
logP11.34ChemAxon
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 Count38ChemAxon
Refractivity225.65 m³·mol⁻¹ChemAxon
Polarizability87.99 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, Positivesplash10-0006-9021100200-7ac23768785e8ae5ab11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9021001000-528865017f3115ad299dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9054011000-5dc5a3edbe57b6fa9fb4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udm-2384701900-0845fc49fbfde05c89e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9661300100-03bc9e9b753e82101031View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9110000000-bc94ff42a3537e49f3e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-3300000900-7ae0dd7d06ff567a2ef9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00l5-4791800300-fb28d1d1d5a62db7f2ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-7911100000-adf716e5ab92330ea23fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-3000007900-d5a619ba6988cb546ee9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-5000019200-fdc092b14ceb5fa4e27bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-3962211000-88b96f3742975ef6559fView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Brain
  • Milk
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
MilkDetected and Quantified105.612 uMNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0011420
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB005556
KNApSAcK IDNot Available
Chemspider ID24769304
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480880
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bitman J, Wood DL: Changes in milk fat phospholipids during lactation. J Dairy Sci. 1990 May;73(5):1208-16. doi: 10.3168/jds.S0022-0302(90)78784-X. [PubMed:2365882 ]