Showing metabocard for PE(16:0/16:1(9Z)) (BMDB0008924)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 17:32:09 UTC
Update Date2020-05-21 16:28:13 UTC
BMDB IDBMDB0008924
Secondary Accession Numbers
  • BMDB08924
Metabolite Identification
Common NamePE(16:0/16:1(9Z))
DescriptionPE(16:0/16:1(9Z)), also known as PE(32:1) or PE(16:0/16:1), 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(16:0/16:1(9Z)) is considered to be a glycerophosphoethanolamine lipid molecule. PE(16:0/16:1(9Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PE(16:0/16:1(9Z)) exists in all living species, ranging from bacteria to humans. PE(16:0/16:1(9Z)) participates in a number of enzymatic reactions, within cattle. In particular, Cytidine monophosphate and PE(16:0/16:1(9Z)) can be biosynthesized from CDP-ethanolamine and DG(16:0/16:1(9Z)/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Furthermore, PE(16:0/16:1(9Z)) can be biosynthesized from PS(16:0/16:1(9Z)); which is mediated by the enzyme phosphatidylserine decarboxylase. Furthermore, PE(16:0/16:1(9Z)) can be biosynthesized from PS(16:0/16:1(9Z)) through its interaction with the enzyme phosphatidylserine decarboxylase. Finally, Cytidine monophosphate and PE(16:0/16:1(9Z)) can be biosynthesized from CDP-ethanolamine and DG(16:0/16:1(9Z)/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. In cattle, PE(16:0/16:1(9Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(16:0/16:1(9Z)) pathway and phosphatidylethanolamine biosynthesis pe(16:0/16:1(9Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-C16:0-2-C16:1(Omega-7)-phosphatidylethanolamine zwitterionChEBI
1-Hexadecanoyl-2-(9Z)-hexadecenoyl-sn-glycero-3-phosphoethanolamineChEBI
1-Hexadecanoyl-2-(9Z)-hexadecenoyl-sn-glycero-3-phosphoethanolamine zwitterionChEBI
1-Hexadecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphoethanolamine zwitterionChEBI
1-Palmitoyl-2-palmitoleoyl-sn-glycero-3-phosphoethanolamine zwitterionChEBI
2-Ammonioethyl (2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(palmitoyloxy)propyl phosphateChEBI
2-Ammonioethyl (2R)-3-(hexadecanoyloxy)-2-[(9Z)-hexadec-9-enoyloxy]propyl phosphateChEBI
2-Ammonioethyl (2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(palmitoyloxy)propyl phosphoric acidGenerator
2-Ammonioethyl (2R)-3-(hexadecanoyloxy)-2-[(9Z)-hexadec-9-enoyloxy]propyl phosphoric acidGenerator
PE(32:1)HMDB
PE(16:0/16:1)HMDB
Phophatidylethanolamine(16:0/16:1)HMDB
GPEtn(32:1)HMDB
1-Palmitoyl-2-palmitoleoyl-sn-glycero-3-phosphoethanolamineHMDB
Phophatidylethanolamine(32:1)HMDB
1-Hexadecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphoethanolamineHMDB
GPEtn(16:0/16:1)HMDB
PE(16:0/16:1(9Z))Lipid Annotator
Chemical FormulaC37H72NO8P
Average Molecular Weight689.956
Monoisotopic Molecular Weight689.49955528
IUPAC Name(2-aminoethoxy)[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(hexadecanoyloxy)propoxy]phosphinic acid
Traditional Name2-aminoethoxy((2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(hexadecanoyloxy)propoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCC\C=C/CCCCCC
InChI Identifier
InChI=1S/C37H72NO8P/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/h14,16,35H,3-13,15,17-34,38H2,1-2H3,(H,41,42)/b16-14-/t35-/m1/s1
InChI KeyCZOSTDZGCCEZTJ-WMHOIYFHSA-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
logP8ALOGPS
logP10.09ChemAxon
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 Count38ChemAxon
Refractivity192.12 m³·mol⁻¹ChemAxon
Polarizability83.77 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 (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-000i-0000139000-b12e4aaaccc2681e66a5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-014i-0000139000-aa6307b3dfee3b43db6eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0030009000-12171a3732af456627d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0030009000-12171a3732af456627d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfr-0190303000-0015dd32be51ac7e92d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000019000-a15ebcb20c9e09cf37dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0005-0003697000-56ae16fcf42feff14d35View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0003693000-109aa247e11666ca7e10View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000010900-d71570caf7eecd1218c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000022900-87a2cd13fd62a0ed0a6fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0100319100-0c628913e7998dddb2caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000019000-97c11016ea748a8c68d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0005-0003697000-787394904a63675b1ebeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0003693000-b1ca674f177c2eb63907View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0030009000-1e8abad5bcb849708214View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0030009000-1e8abad5bcb849708214View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfr-0190303000-dec081ccf7e7ad5e92b1View 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 IDHMDB0008924
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB026114
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52924925
PDB IDNot Available
ChEBI ID73999
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(16:0/16:1(9Z)/0:0) → Cytidine monophosphate + PE(16:0/16:1(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(16:0/16:1(9Z)) → PE(16:0/16:1(9Z)) + Carbon dioxidedetails