Showing metabocard for PE(16:0/18:1(9Z)) (BMDB0008927)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
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Record Information
Version1.0
Creation Date2016-10-03 17:32:12 UTC
Update Date2020-05-21 16:28:13 UTC
BMDB IDBMDB0008927
Secondary Accession Numbers
  • BMDB08927
Metabolite Identification
Common NamePE(16:0/18:1(9Z))
DescriptionPE(16:0/18:1(9Z)), also known as pe(16:0/18:1(9z)) or pe(16:0/18:1(9z)), 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(16:0/18:1(9Z)) is considered to be a glycerophosphoethanolamine lipid molecule. PE(16:0/18:1(9Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PE(16:0/18:1(9Z)) exists in all living species, ranging from bacteria to humans. PE(16:0/18:1(9Z)) participates in a number of enzymatic reactions, within cattle. In particular, Cytidine monophosphate and PE(16:0/18:1(9Z)) can be biosynthesized from CDP-ethanolamine and DG(16:0/18:1(9Z)/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Furthermore, PE(16:0/18:1(9Z)) can be biosynthesized from PS(16:0/18:1(9Z)); which is mediated by the enzyme phosphatidylserine decarboxylase. Furthermore, PE(16:0/18:1(9Z)) can be biosynthesized from PS(16:0/18:1(9Z)); which is catalyzed by the enzyme phosphatidylserine decarboxylase. Finally, Cytidine monophosphate and PE(16:0/18:1(9Z)) can be biosynthesized from CDP-ethanolamine and DG(16:0/18:1(9Z)/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. In cattle, PE(16:0/18:1(9Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(16:0/18:1(9Z)) pathway and phosphatidylethanolamine biosynthesis pe(16:0/18:1(9Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Chemical FormulaC39H76NO8P
Average Molecular Weight718.01
Monoisotopic Molecular Weight717.530855409
IUPAC Name(2-aminoethoxy)[(2R)-3-(hexadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy((2R)-3-(hexadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C39H76NO8P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-39(42)48-37(36-47-49(43,44)46-34-33-40)35-45-38(41)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h17-18,37H,3-16,19-36,40H2,1-2H3,(H,43,44)/b18-17-/t37-/m1/s1
InChI KeyFHQVHHIBKUMWTI-OTMQOFQLSA-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
logP8.44ALOGPS
logP10.98ChemAxon
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
Refractivity201.32 m³·mol⁻¹ChemAxon
Polarizability88.32 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_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - QqQ 1V, negativesplash10-001i-0090000100-2e9d9a8d8feca579aacaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - IT 40V, negativesplash10-05o0-0090300300-5dca79ab504547b01f82View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 43V, positivesplash10-0159-0001493600-5907ebc5c0953d384058View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 2V, positivesplash10-014i-0000010900-c9437cd99b6b171adfdcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-014i-0000030900-bd57a871db71d1bf70dfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 6V, positivesplash10-016r-0001070900-d2f866f61d4f92564a28View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 8V, positivesplash10-00or-0001090600-dd0bbf82cb7b06430dfcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-004i-0001090300-a607c44099ff83629c56View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 12V, positivesplash10-004i-0001090300-82b4814349c972c80cdeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 16V, positivesplash10-004i-1002090100-497394a1af38d43c2314View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 18V, positivesplash10-004i-0002090000-5f6262b8cc3cf72935c6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-004i-2011090000-cd010912f5172b6da54fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 23V, positivesplash10-004i-3213090000-1548550e35e3d9c8fcf9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 27V, positivesplash10-004i-5032090000-9b380fedebc72ca568c7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - IT 30V, positivesplash10-004i-0000090200-c4efcd6150cb11f1fb9aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 20V, positivesplash10-016r-0000040900-a387fa9204d6a9e5d009View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 30V, positivesplash10-004i-0000090100-fb4b6d8a1afa5d49f1e0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 40V, positivesplash10-004i-0000090000-ad39b1973c677a1cdd07View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 50V, positivesplash10-004i-1110090000-4175c9cf5ace54980f84View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0030000900-dd1a62d29ee1a90ddd63View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0030000900-dd1a62d29ee1a90ddd63View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05o0-0190300300-262655b873a3fd0a874cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000010900-6f573d993dec08dd3c88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00or-0003690700-f71e3df43eaec8018c6fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0003690300-952c4e3ba35083fefda6View in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
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 IDHMDB0008927
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB026117
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283496
PDB IDNot Available
ChEBI ID73007
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(16:0/18:1(9Z)/0:0) → Cytidine monophosphate + PE(16:0/18:1(9Z))details
Enzyme Details
2. Phosphatidylethanolamine N-methyltransferase
General function:
Involved in phosphatidylethanolamine N-methyltransferas
Specific function:
Catalyzes the three sequential steps of the methylation pathway of phosphatidylcholine biosynthesis, the SAM-dependent methylation of phosphatidylethanolamine (PE) to phosphatidylmonomethylethanolamine (PMME), PMME to phosphatidyldimethylethanolamine (PDME), and PDME to phosphatidylcholine (PC).
Gene Name:
PEMT
Uniprot ID:
Q7YRH6
Molecular weight:
22018.0
Reactions
S-Adenosylmethionine + PE(16:0/18:1(9Z)) → S-Adenosylhomocysteine + PE-NMe(16:0/18:1(9Z))details
Enzyme Details
3. 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(16:0/18:1(9Z)) → PE(16:0/18:1(9Z)) + Carbon dioxidedetails