Showing metabocard for PE(18:0/18:4(6Z,9Z,12Z,15Z)) (BMDB0008997)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-10-03 17:33:40 UTC
Update Date2020-05-21 16:26:27 UTC
BMDB IDBMDB0008997
Secondary Accession Numbers
  • BMDB08997
Metabolite Identification
Common NamePE(18:0/18:4(6Z,9Z,12Z,15Z))
DescriptionPE(18:0/18:4(6Z,9Z,12Z,15Z)), also known as GPEtn(36:4) or GPEtn(18:0/18:4), 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(18:0/18:4(6Z,9Z,12Z,15Z)) is considered to be a glycerophosphoethanolamine lipid molecule. PE(18:0/18:4(6Z,9Z,12Z,15Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PE(18:0/18:4(6Z,9Z,12Z,15Z)) participates in a number of enzymatic reactions, within cattle. In particular, PE(18:0/18:4(6Z,9Z,12Z,15Z)) can be biosynthesized from PS(18:0/18:4(6Z,9Z,12Z,15Z)); which is mediated by the enzyme phosphatidylserine decarboxylase. Furthermore, Cytidine monophosphate and PE(18:0/18:4(6Z,9Z,12Z,15Z)) can be biosynthesized from CDP-ethanolamine and DG(18:0/18:4(6Z,9Z,12Z,15Z)/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Furthermore, Cytidine monophosphate and PE(18:0/18:4(6Z,9Z,12Z,15Z)) can be biosynthesized from CDP-ethanolamine and DG(18:0/18:4(6Z,9Z,12Z,15Z)/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Finally, PE(18:0/18:4(6Z,9Z,12Z,15Z)) can be biosynthesized from PS(18:0/18:4(6Z,9Z,12Z,15Z)) through its interaction with the enzyme phosphatidylserine decarboxylase. In cattle, PE(18:0/18:4(6Z,9Z,12Z,15Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(18:0/18:4(6Z,9Z,12Z,15Z)) pathway and phosphatidylcholine biosynthesis PC(18:0/18:4(6Z,9Z,12Z,15Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Phophatidylethanolamine(18:0/18:4)HMDB
GPEtn(36:4)HMDB
GPEtn(18:0/18:4)HMDB
PE(18:0/18:4)HMDB
PE(36:4)HMDB
1-Stearoyl-2-stearidonoyl-sn-glycero-3-phosphoethanolamineHMDB
1-Octadecanoyl-2-(6Z,9Z,12Z,15Z-octadecatetraenoyl)-sn-glycero-3-phosphoethanolamineHMDB
Phophatidylethanolamine(36:4)HMDB
PE(18:0/18:4(6Z,9Z,12Z,15Z))Lipid Annotator
Chemical FormulaC41H74NO8P
Average Molecular Weight740.0019
Monoisotopic Molecular Weight739.515204861
IUPAC Name(2-aminoethoxy)[(2R)-2-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]-3-(octadecanoyloxy)propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-2-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]-3-(octadecanoyloxy)propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C41H74NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-40(43)47-37-39(38-49-51(45,46)48-36-35-42)50-41(44)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h6,8,12,14,18,20,24,26,39H,3-5,7,9-11,13,15-17,19,21-23,25,27-38,42H2,1-2H3,(H,45,46)/b8-6-,14-12-,20-18-,26-24-/t39-/m1/s1
InChI KeyKZLUVTCXBFEIFJ-XGLJQOENSA-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
logP8.64ALOGPS
logP10.78ChemAxon
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 Count39ChemAxon
Refractivity213.87 m³·mol⁻¹ChemAxon
Polarizability88.13 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, Negativesplash10-000i-0030000900-3ba09dd753cebdbabbb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0030000900-3ba09dd753cebdbabbb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0040-0190300300-3a8bb20586fc133418aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000010900-7a7f24af2fd6d0accc42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0005-0003690700-edc009e10cf1f6053be9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0003690300-7fce7999157c6be037b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000001900-e8c336bb746e73b15694View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000001900-3c0250af56fb910b1448View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0100201900-938a69e1d7edcb018ca9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0030000900-ad12525e5fbbeb125bc6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0030000900-ad12525e5fbbeb125bc6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0040-0190300300-36b51d4f77589e19ed6eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000010900-430baf43f79ec38a2862View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0005-0003690700-32fa906a7b89a69f5736View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0003690300-33d8094bd80d6b490244View 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 IDHMDB0008997
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 Compound52924904
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(18:0/18:4(6Z,9Z,12Z,15Z)/0:0) → Cytidine monophosphate + PE(18:0/18:4(6Z,9Z,12Z,15Z))details