Showing metabocard for PE(18:0/20:0) (BMDB0008998)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 17:33:41 UTC
Update Date2020-05-21 16:28:14 UTC
BMDB IDBMDB0008998
Secondary Accession Numbers
  • BMDB08998
Metabolite Identification
Common NamePE(18:0/20:0)
DescriptionPE(18:0/20:0), also known as GPEtn(38:0), 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(18:0/20:0) is considered to be a glycerophosphoethanolamine lipid molecule. PE(18:0/20:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PE(18:0/20:0) exists in all living organisms, ranging from bacteria to humans. PE(18:0/20:0) participates in a number of enzymatic reactions, within cattle. In particular, Cytidine monophosphate and PE(18:0/20:0) can be biosynthesized from CDP-ethanolamine and DG(18:0/20:0/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Furthermore, PE(18:0/20:0) can be biosynthesized from PS(18:0/20:0) through its interaction with the enzyme phosphatidylserine decarboxylase. Furthermore, PE(18:0/20:0) can be biosynthesized from PS(18:0/20:0) through its interaction with the enzyme phosphatidylserine decarboxylase. Finally, Cytidine monophosphate and PE(18:0/20:0) can be biosynthesized from CDP-ethanolamine and DG(18:0/20:0/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. In cattle, PE(18:0/20:0) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(18:0/20:0) pathway and phosphatidylethanolamine biosynthesis pe(18:0/20:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Phophatidylethanolamine(18:0/20:0)HMDB
GPEtn(18:0/20:0)HMDB
1-Stearoyl-2-arachidonyl-sn-glycero-3-phosphoethanolamineHMDB
Phophatidylethanolamine(38:0)HMDB
GPEtn(38:0)HMDB
1-Octadecanoyl-2-eicosanoyl-sn-glycero-3-phosphoethanolamineHMDB
PE(38:0)HMDB
PE(18:0/20:0)Lipid Annotator
Chemical FormulaC43H86NO8P
Average Molecular Weight776.134
Monoisotopic Molecular Weight775.609105731
IUPAC Name(2-aminoethoxy)[(2R)-2-(icosanoyloxy)-3-(octadecanoyloxy)propoxy]phosphinic acid
Traditional Name2-aminoethoxy((2R)-2-(icosanoyloxy)-3-(octadecanoyloxy)propoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C43H86NO8P/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/h41H,3-40,44H2,1-2H3,(H,47,48)/t41-/m1/s1
InChI KeyTZINTCMFTOUPSN-VQJSHJPSSA-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
logP9.2ALOGPS
logP13.12ChemAxon
logS-7.2ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area134.38 ŲChemAxon
Rotatable Bond Count45ChemAxon
Refractivity218.61 m³·mol⁻¹ChemAxon
Polarizability97.85 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0011000900-4b0862622120ab996c71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0011000900-4b0862622120ab996c71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03lr-0399410600-88923c0936b3cdd8fb63View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000001900-996a5650ae3eef48ad47View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002r-0003419700-422ddc13e256003640d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0003419300-d7605597e8ce67bf3e95View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000001900-299d3d516bc91c900ff9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052b-0000001900-5b9159548ba9c942e567View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0100201900-7ab1be3fbddeff237415View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000001900-0b1fcb7771147698de92View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002r-0003419700-f928cce44e52cfc25fc5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0003419300-46b44531606a166ba6fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0011000900-a044e06b5d24a28c67b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0011000900-a044e06b5d24a28c67b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03lr-0399410600-1375b413633373721735View 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 IDHMDB0008998
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB026188
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound449007
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(18:0/20:0/0:0) → Cytidine monophosphate + PE(18:0/20:0)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(18:0/20:0) → PE(18:0/20:0) + Carbon dioxidedetails