Showing metabocard for PE(16:1(9Z)/20:3(8Z,11Z,14Z)) (BMDB0008969)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 17:33:05 UTC
Update Date2020-05-21 16:28:14 UTC
BMDB IDBMDB0008969
Secondary Accession Numbers
  • BMDB08969
Metabolite Identification
Common NamePE(16:1(9Z)/20:3(8Z,11Z,14Z))
DescriptionPE(16:1(9Z)/20:3(8Z,11Z,14Z)), also known as GPEtn(36:4) or pe(16:1(9z)/20:3(8z,11z,14z)), 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. PE(16:1(9Z)/20:3(8Z,11Z,14Z)) is possibly soluble (in water) and a very strong basic compound (based on its pKa). PE(16:1(9Z)/20:3(8Z,11Z,14Z)) participates in a number of enzymatic reactions, within cattle. In particular, PE(16:1(9Z)/20:3(8Z,11Z,14Z)) can be biosynthesized from PS(16:1(9Z)/20:3(8Z,11Z,14Z)) through the action of the enzyme phosphatidylserine decarboxylase. Furthermore, Cytidine monophosphate and PE(16:1(9Z)/20:3(8Z,11Z,14Z)) can be biosynthesized from CDP-ethanolamine and DG(16:1(9Z)/20:3(8Z,11Z,14Z)/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Furthermore, Cytidine monophosphate and PE(16:1(9Z)/20:3(8Z,11Z,14Z)) can be biosynthesized from CDP-ethanolamine and DG(16:1(9Z)/20:3(8Z,11Z,14Z)/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Finally, PE(16:1(9Z)/20:3(8Z,11Z,14Z)) can be biosynthesized from PS(16:1(9Z)/20:3(8Z,11Z,14Z)); which is catalyzed by the enzyme phosphatidylserine decarboxylase. In cattle, PE(16:1(9Z)/20:3(8Z,11Z,14Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(16:1(9Z)/20:3(8Z,11Z,14Z)) pathway and phosphatidylcholine biosynthesis PC(16:1(9Z)/20:3(8Z,11Z,14Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
GPEtn(36:4)HMDB
PE(36:4)HMDB
Phophatidylethanolamine(16:1/20:3)HMDB
1-Palmitoleoyl-2-homo-g-linolenoyl-sn-glycero-3-phosphoethanolamineHMDB
GPEtn(16:1/20:3)HMDB
PE(16:1/20:3)HMDB
1-(9Z-Hexadecenoyl)-2-(8Z,11Z,14Z-eicosatrienoyl)-sn-glycero-3-phosphoethanolamineHMDB
Phophatidylethanolamine(36:4)HMDB
PE(16:1(9Z)/20:3(8Z,11Z,14Z))Lipid Annotator
Chemical FormulaC43H78NO8P
Average Molecular Weight768.0551
Monoisotopic Molecular Weight767.546504989
IUPAC Name(2-aminoethoxy)[(2R)-2-[(10Z,13Z,16Z)-docosa-10,13,16-trienoyloxy]-3-[(9Z)-hexadec-9-enoyloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-2-[(10Z,13Z,16Z)-docosa-10,13,16-trienoyloxy]-3-[(9Z)-hexadec-9-enoyloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCC\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C43H78NO8P/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-26-28-30-32-34-36-43(46)52-41(40-51-53(47,48)50-38-37-44)39-49-42(45)35-33-31-29-27-25-23-16-14-12-10-8-6-4-2/h11,13-14,16-18,20-21,41H,3-10,12,15,19,22-40,44H2,1-2H3,(H,47,48)/b13-11-,16-14-,18-17-,21-20-/t41-/m1/s1
InChI KeyJQKIMGMIMCFLFR-IEECDEBMSA-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
logP8.93ALOGPS
logP11.67ChemAxon
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 Count41ChemAxon
Refractivity223.08 m³·mol⁻¹ChemAxon
Polarizability92.81 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, Negativesplash10-014i-0011000900-42f06c363b373829be56View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0011000900-42f06c363b373829be56View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uz9-0399330600-bb780f7955d288bd8798View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000001900-a80ac2397e57004baca7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00or-0003339700-20d5f7619d6e0b7f0166View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0003339300-145187606a4979276280View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0011000900-3dec0489f66430c38b0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0011000900-3dec0489f66430c38b0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uz9-0399330600-2a16fc210a631916722eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000001900-6605169b5cd24413c472View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0007-0000001900-c91b6bc5b76b3e4c8c04View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0100201900-02b60139521a212f53ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000001900-49e279451bfe98179b71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00or-0003339700-0ce5dd775c46bbf250d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0003339300-db17f0f73da8d88036c0View 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 IDHMDB0008969
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB026159
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53479598
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Ethanolaminephosphotransferase 1
General function:
Involved in ethanolaminephosphotransferase activity
Specific function:
Catalyzes phosphatidylethanolamine biosynthesis from CDP-ethanolamine. It thereby plays a central role in the formation and maintenance of vesicular membranes. Involved in the foramtion of phosphatidylethanolamine via 'Kennedy' pathway (By similarity).
Gene Name:
SELENOI
Uniprot ID:
Q17QM4
Molecular weight:
45214.0
Reactions
CDP-Ethanolamine + DG(16:1(9Z)/20:3(8Z,11Z,14Z)/0:0) → Cytidine monophosphate + PE(16:1(9Z)/20:3(8Z,11Z,14Z))details
Enzyme Details
2. Phosphatidylserine decarboxylase proenzyme, mitochondrial
General function:
Not Available
Specific function:
Catalyzes the formation of phosphatidylethanolamine (PtdEtn) from phosphatidylserine (PtdSer). Plays a central role in phospholipid metabolism and in the interorganelle trafficking of phosphatidylserine.
Gene Name:
PISD
Uniprot ID:
Q58DH2
Molecular weight:
47244.0
Reactions
PS(16:1(9Z)/20:3(8Z,11Z,14Z)) → PE(16:1(9Z)/20:3(8Z,11Z,14Z)) + Carbon dioxidedetails