Showing metabocard for PE(18:0/20:4(5Z,8Z,11Z,14Z)) (BMDB0009003)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 17:33:47 UTC
Update Date2020-05-21 16:28:14 UTC
BMDB IDBMDB0009003
Secondary Accession Numbers
  • BMDB09003
Metabolite Identification
Common NamePE(18:0/20:4(5Z,8Z,11Z,14Z))
DescriptionPE(18:0/20:4(5Z,8Z,11Z,14Z)), also known as PE(18:0/20:4) or Pe(18:0/20:4(5z,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. Thus, PE(18:0/20:4(5Z,8Z,11Z,14Z)) is considered to be a glycerophosphoethanolamine lipid molecule. PE(18:0/20:4(5Z,8Z,11Z,14Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PE(18:0/20:4(5Z,8Z,11Z,14Z)) participates in a number of enzymatic reactions, within cattle. In particular, PE(18:0/20:4(5Z,8Z,11Z,14Z)) can be biosynthesized from PS(18:0/20:4(5Z,8Z,11Z,14Z)); which is catalyzed by the enzyme phosphatidylserine decarboxylase. Furthermore, Cytidine monophosphate and PE(18:0/20:4(5Z,8Z,11Z,14Z)) can be biosynthesized from CDP-ethanolamine and DG(18:0/20:4(5Z,8Z,11Z,14Z)/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Furthermore, Cytidine monophosphate and PE(18:0/20:4(5Z,8Z,11Z,14Z)) can be biosynthesized from CDP-ethanolamine and DG(18:0/20:4(5Z,8Z,11Z,14Z)/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Finally, PE(18:0/20:4(5Z,8Z,11Z,14Z)) can be biosynthesized from PS(18:0/20:4(5Z,8Z,11Z,14Z)); which is mediated by the enzyme phosphatidylserine decarboxylase. In cattle, PE(18:0/20:4(5Z,8Z,11Z,14Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(18:0/20:4(5Z,8Z,11Z,14Z)) pathway and phosphatidylcholine biosynthesis PC(18:0/20:4(5Z,8Z,11Z,14Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamineChEBI
1-Octadecanoyl-2-(5Z,8Z,11Z,14Z)-icosatetraenoyl-sn-glycero-3-phosphoethanolamine zwitterionChEBI
1-Stearoyl-2-arachidonoyl-gpeChEBI
1-Stearoyl-2-arachidonoyl-gpe (18:0/20:4)ChEBI
GPE(18:0/20:4(5Z,8Z,11Z,14Z))ChEBI
GPE(18:0/20:4)ChEBI
PE(18:0/20:4)ChEBI
GPEtn(38:4)HMDB
Phophatidylethanolamine(38:4)HMDB
1-Stearoyl-2-arachidonoyl-sn-glycero-3-phosphoethanolamineHMDB
GPEtn(18:0/20:4)HMDB
PE(38:4)HMDB
1-Octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamineHMDB
Phophatidylethanolamine(18:0/20:4)HMDB
1-Stearoyl-2-arachidonoyl phosphatidylethanolamineHMDB
1-Stearoyl-2-arachidonoyl-sn-glycero-3-phosphorylethanolamineHMDB
1-Stearoyl-2-arachidonoyl-sn-glycero-phosphatidylethanolamineHMDB
GPE(18:0/20:4n6)HMDB
GPE(18:0/20:4W6)HMDB
GPE(38:4)HMDB
GPEtn(18:0/20:4(5Z,8Z,11Z,14Z))HMDB
GPEtn(18:0/20:4n6)HMDB
GPEtn(18:0/20:4W6)HMDB
PE(18:0/20:4N6)HMDB
PE(18:0/20:4W6)HMDB
Phosphatidylethanolamine(18:0/20:4(5Z,8Z,11Z,14Z))HMDB
Phosphatidylethanolamine(18:0/20:4)HMDB
Phosphatidylethanolamine(18:0/20:4n6)HMDB
Phosphatidylethanolamine(18:0/20:4W6)HMDB
Phosphatidylethanolamine(38:4)HMDB
SAPEHMDB
PE(18:0/20:4(5Z,8Z,11Z,14Z))Lipid Annotator
Chemical FormulaC43H78NO8P
Average Molecular Weight768.0551
Monoisotopic Molecular Weight767.546504989
IUPAC Name(2-aminoethoxy)[(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-(octadecanoyloxy)propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-(octadecanoyloxy)propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C43H78NO8P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-43(46)52-41(40-51-53(47,48)50-38-37-44)39-49-42(45)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h11,13,17,19,22,24,28,30,41H,3-10,12,14-16,18,20-21,23,25-27,29,31-40,44H2,1-2H3,(H,47,48)/b13-11-,19-17-,24-22-,30-28-/t41-/m1/s1
InChI KeyANRKEHNWXKCXDB-BHFWLYLHSA-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
logP9.04ALOGPS
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
Polarizability92.68 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-ac48aac8efee764d40aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0011000900-ac48aac8efee764d40aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uz9-0399410600-7f2f1c0d304acb650115View 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-0003419700-6e990e436ab77e2a70a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0003419300-9cd0ac4bc79a967fb37bView 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-f1dd1ff78582d65cb7deView 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-0003419700-52b30028f0abf43cc9ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0003419300-22e70d3183d8d280b6a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0011000900-7a09e4713c6f6f61b5bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0011000900-7a09e4713c6f6f61b5bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uz9-0399410600-13aeee9170c7d2fe2cceView 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 IDHMDB0009003
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5289133
PDB IDNot Available
ChEBI ID78268
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(18:0/20:4(5Z,8Z,11Z,14Z)/0:0) → Cytidine monophosphate + PE(18:0/20:4(5Z,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(18:0/20:4(5Z,8Z,11Z,14Z)) → PE(18:0/20:4(5Z,8Z,11Z,14Z)) + Carbon dioxidedetails