Showing metabocard for PE(16:0/20:3(8Z,11Z,14Z)) (BMDB0008936)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 17:32:24 UTC
Update Date2020-05-21 16:28:13 UTC
BMDB IDBMDB0008936
Secondary Accession Numbers
  • BMDB08936
Metabolite Identification
Common NamePE(16:0/20:3(8Z,11Z,14Z))
DescriptionPE(16:0/20:3(8Z,11Z,14Z)), also known as PE(16:0/20:3) or GPEtn(36:3), 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. Thus, PE(16:0/20:3(8Z,11Z,14Z)) is considered to be a glycerophosphoethanolamine lipid molecule. PE(16:0/20:3(8Z,11Z,14Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PE(16:0/20:3(8Z,11Z,14Z)) participates in a number of enzymatic reactions, within cattle. In particular, PE(16:0/20:3(8Z,11Z,14Z)) can be biosynthesized from PS(16:0/20:3(8Z,11Z,14Z)) through its interaction with the enzyme phosphatidylserine decarboxylase. Furthermore, Cytidine monophosphate and PE(16:0/20:3(8Z,11Z,14Z)) can be biosynthesized from CDP-ethanolamine and DG(16:0/20:3(8Z,11Z,14Z)/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Furthermore, Cytidine monophosphate and PE(16:0/20:3(8Z,11Z,14Z)) can be biosynthesized from CDP-ethanolamine and DG(16:0/20:3(8Z,11Z,14Z)/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Finally, PE(16:0/20:3(8Z,11Z,14Z)) can be biosynthesized from PS(16:0/20:3(8Z,11Z,14Z)) through its interaction with the enzyme phosphatidylserine decarboxylase. In cattle, PE(16:0/20:3(8Z,11Z,14Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(16:0/20:3(8Z,11Z,14Z)) pathway and phosphatidylcholine biosynthesis PC(16:0/20:3(8Z,11Z,14Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Hexadecanoyl-2-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphoethanolamineChEBI
1-Hexadecanoyl-2-[(8Z,11Z,14Z)-eicosatrienoyl]-sn-glycero-3-phosphoethanolamineChEBI
1-Hexadecanoyl-2-[(8Z,11Z,14Z)-icosatrienoyl]-sn-glycero-3-phosphoethanolamineChEBI
1-Palmitoyl-2-(8Z,11Z,14Z-eicosatrienoyl)-sn-glycero-3-phosphoethanolamineChEBI
1-Palmitoyl-2-(8Z,11Z,14Z-icosatrienoyl)-sn-glycero-3-phosphoethanolamineChEBI
GPE(16:0/20:3)ChEBI
GPEtn(16:0/20:3)ChEBI
GPEtn(16:0/20:3n6)ChEBI
GPEtn(16:0/20:3W6)ChEBI
GPEtn(36:3)ChEBI
PE(16:0/20:3)ChEBI
PE(16:0/20:3N6)ChEBI
PE(16:0/20:3W6)ChEBI
PE(36:3)ChEBI
Phosphatidylethanolamine(16:0/20:3)ChEBI
Phosphatidylethanolamine(16:0/20:3n6)ChEBI
Phosphatidylethanolamine(16:0/20:3W6)ChEBI
Phosphatidylethanolamine(36:3)ChEBI
Phophatidylethanolamine(36:3)HMDB
Phophatidylethanolamine(16:0/20:3)HMDB
1-Palmitoyl-2-homo-g-linolenoyl-sn-glycero-3-phosphoethanolamineHMDB
1-Hexadecanoyl-2-(8Z,11Z,14Z-eicosatrienoyl)-sn-glycero-3-phosphoethanolamineHMDB
PE(16:0/20:3(8Z,11Z,14Z))Lipid Annotator
Chemical FormulaC41H76NO8P
Average Molecular Weight742.0178
Monoisotopic Molecular Weight741.530854925
IUPAC Name(2-aminoethoxy)[(2R)-3-(hexadecanoyloxy)-2-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-3-(hexadecanoyloxy)-2-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C41H76NO8P/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-41(44)50-39(38-49-51(45,46)48-36-35-42)37-47-40(43)33-31-29-27-25-23-21-16-14-12-10-8-6-4-2/h11,13,17-18,20,22,39H,3-10,12,14-16,19,21,23-38,42H2,1-2H3,(H,45,46)/b13-11-,18-17-,22-20-/t39-/m1/s1
InChI KeyLMWFNZUKABEGHS-CISNCOODSA-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 Descriptors
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
logP8.77ALOGPS
logP11.14ChemAxon
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 Count40ChemAxon
Refractivity212.76 m³·mol⁻¹ChemAxon
Polarizability89.78 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, Positivesplash10-0006-9040200200-965db4f619ca0f6141eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9140001000-26ed667c27e88302f92cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9172012000-0a9832fdcf3e0c98b7cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4r-1192201200-c6c4731ae679bfe594f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a73-5391100000-aeb6f2794e03fef70f6dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9110000000-e359d8953dc4c37f1639View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000001900-14741bc15c899010122fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udl-0003419700-6d5a75ad64a5f6fa1dadView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0003419300-597ae8ca6a6814e67813View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0011000900-11a0b288c5d04d939ca3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0011000900-11a0b288c5d04d939ca3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0399410600-f27f730f32000e91d8bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000001900-b5faf9a389ddc4f385f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03k9-0000001900-76cbb35947be695c5de5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0100201900-fd25f9bcca6c9257d40dView 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 IDHMDB0008936
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB026126
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52924920
PDB IDNot Available
ChEBI ID133655
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(16:0/20:3(8Z,11Z,14Z)/0:0) → Cytidine monophosphate + PE(16:0/20:3(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(16:0/20:3(8Z,11Z,14Z)) → PE(16:0/20:3(8Z,11Z,14Z)) + Carbon dioxidedetails