Showing metabocard for PE(16:1(9Z)/16:1(9Z)) (BMDB0008957)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 17:32:51 UTC
Update Date2020-05-21 16:28:13 UTC
BMDB IDBMDB0008957
Secondary Accession Numbers
  • BMDB08957
Metabolite Identification
Common NamePE(16:1(9Z)/16:1(9Z))
DescriptionPE(16:1(9Z)/16:1(9Z)), also known as GPEtn(32:2) or PE(16:1/16:1), 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(16:1(9Z)/16:1(9Z)) is considered to be a glycerophosphoethanolamine lipid molecule. PE(16:1(9Z)/16:1(9Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PE(16:1(9Z)/16:1(9Z)) exists in all living species, ranging from bacteria to humans. PE(16:1(9Z)/16:1(9Z)) participates in a number of enzymatic reactions, within cattle. In particular, PE(16:1(9Z)/16:1(9Z)) can be biosynthesized from PS(16:1(9Z)/16:1(9Z)) through the action of the enzyme phosphatidylserine decarboxylase. Furthermore, Cytidine monophosphate and PE(16:1(9Z)/16:1(9Z)) can be biosynthesized from CDP-ethanolamine and DG(16:1(9Z)/16:1(9Z)/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Furthermore, Cytidine monophosphate and PE(16:1(9Z)/16:1(9Z)) can be biosynthesized from CDP-ethanolamine and DG(16:1(9Z)/16:1(9Z)/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Finally, PE(16:1(9Z)/16:1(9Z)) can be biosynthesized from PS(16:1(9Z)/16:1(9Z)) through the action of the enzyme phosphatidylserine decarboxylase. In cattle, PE(16:1(9Z)/16:1(9Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(16:1(9Z)/16:1(9Z)) pathway and phosphatidylcholine biosynthesis PC(16:1(9Z)/16:1(9Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2-Di-(9Z-hexadecenoyl)-sn-glycero-3-phosphoethanolamineChEBI
1,2-Dipalmitoleoyl-sn-glycero-3-phosphoethanolamine zwitterionChEBI
GPEtn(32:2)HMDB
PE(32:2)HMDB
PE(16:1/16:1)HMDB
Phophatidylethanolamine(16:1/16:1)HMDB
GPEtn(16:1/16:1)HMDB
Phophatidylethanolamine(32:2)HMDB
1,2-Di(9Z-hexadecenoyl)-rac-glycero-3-phosphoethanolamineHMDB
1,2-Dipalmitoleoyl-rac-glycero-3-phosphoethanolamineHMDB
PE(16:1(9Z)/16:1(9Z))Lipid Annotator
Chemical FormulaC37H70NO8P
Average Molecular Weight687.94
Monoisotopic Molecular Weight687.483905216
IUPAC Name(2-aminoethoxy)[(2R)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy((2R)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCC\C=C/CCCCCC
InChI Identifier
InChI=1S/C37H70NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-36(39)43-33-35(34-45-47(41,42)44-32-31-38)46-37(40)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13-16,35H,3-12,17-34,38H2,1-2H3,(H,41,42)/b15-13-,16-14-/t35-/m1/s1
InChI KeyPGPMCWZMPPZJML-NAFNZUQFSA-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
logP7.89ALOGPS
logP9.73ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area134.38 ŲChemAxon
Rotatable Bond Count37ChemAxon
Refractivity193.24 m³·mol⁻¹ChemAxon
Polarizability82.09 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, Negativesplash10-000i-0010009000-9467665e0186731a29a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0010009000-9467665e0186731a29a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-0390306000-8d97c6f6993df945bdd5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000019000-7de5e69af9b79891360eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000b-0001397000-fa7705935123e40e14ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0001393000-f9f1155e5ab5c1a08747View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000010900-d60ec87cde7d1e3d1bf5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03xr-0000022900-5d7005bec5982bccbceeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0100119100-5bfce3ea4c2b943f20faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0010009000-2985386274ae208b2fe2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0010009000-2985386274ae208b2fe2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-0390306000-fe45e046f9b9e7f53f8cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000019000-8c491c4aae9d3cb0e6dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000b-0001397000-4e8f38ec1ebb24c7f11bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0001393000-89b7c4d5ec9939688f97View 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
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 IDHMDB0008957
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB026147
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9546809
PDB IDNot Available
ChEBI ID138145
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(16:1(9Z)/16:1(9Z)/0:0) → Cytidine monophosphate + PE(16:1(9Z)/16:1(9Z))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(16:1(9Z)/16:1(9Z)) → PE(16:1(9Z)/16:1(9Z)) + Carbon dioxidedetails