Showing metabocard for PE(16:1(9Z)/18:2(9Z,12Z)) (BMDB0008961)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 17:32:56 UTC
Update Date2020-05-21 16:28:14 UTC
BMDB IDBMDB0008961
Secondary Accession Numbers
  • BMDB08961
Metabolite Identification
Common NamePE(16:1(9Z)/18:2(9Z,12Z))
DescriptionPE(16:1(9Z)/18:2(9Z,12Z)), also known as GPEtn(34:3) or pe(16:1(9z)/18:2(9z,12z)), 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)/18:2(9Z,12Z)) is considered to be a glycerophosphoethanolamine lipid molecule. PE(16:1(9Z)/18:2(9Z,12Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PE(16:1(9Z)/18:2(9Z,12Z)) participates in a number of enzymatic reactions, within cattle. In particular, PE(16:1(9Z)/18:2(9Z,12Z)) can be biosynthesized from PS(16:1(9Z)/18:2(9Z,12Z)); which is catalyzed by the enzyme phosphatidylserine decarboxylase. Furthermore, Cytidine monophosphate and PE(16:1(9Z)/18:2(9Z,12Z)) can be biosynthesized from CDP-ethanolamine and DG(16:1(9Z)/18:2(9Z,12Z)/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Furthermore, Cytidine monophosphate and PE(16:1(9Z)/18:2(9Z,12Z)) can be biosynthesized from CDP-ethanolamine and DG(16:1(9Z)/18:2(9Z,12Z)/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Finally, PE(16:1(9Z)/18:2(9Z,12Z)) can be biosynthesized from PS(16:1(9Z)/18:2(9Z,12Z)); which is catalyzed by the enzyme phosphatidylserine decarboxylase. In cattle, PE(16:1(9Z)/18:2(9Z,12Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(16:1(9Z)/18:2(9Z,12Z)) pathway and phosphatidylcholine biosynthesis PC(16:1(9Z)/18:2(9Z,12Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Palmitoleoyl-2-linoleoyl-sn-glycero-3-phosphoethanolamineHMDB
GPEtn(34:3)HMDB
Phophatidylethanolamine(16:1/18:2)HMDB
Phophatidylethanolamine(34:3)HMDB
PE(34:3)HMDB
GPEtn(16:1/18:2)HMDB
PE(16:1/18:2)HMDB
1-(9Z-Hexadecenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphoethanolamineHMDB
PE(16:1(9Z)/18:2(9Z,12Z))Lipid Annotator
Chemical FormulaC39H72NO8P
Average Molecular Weight713.9646
Monoisotopic Molecular Weight713.499554797
IUPAC Name(2-aminoethoxy)[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C39H72NO8P/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/h11,13-14,16-18,37H,3-10,12,15,19-36,40H2,1-2H3,(H,43,44)/b13-11-,16-14-,18-17-/t37-/m1/s1
InChI KeySSRRIJSEUKHYFB-DFCPKGTFSA-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
logP8.27ALOGPS
logP10.25ChemAxon
logS-6.9ALOGPS
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
Refractivity203.56 m³·mol⁻¹ChemAxon
Polarizability85.1 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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0030000900-32c8fc08c1934555367bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0030000900-32c8fc08c1934555367bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0w4i-0190300300-86657b8b78a96b59b119View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0030000900-3e4359ccb841275e012fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0030000900-3e4359ccb841275e012fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0w4i-0190300300-a090cd2415ea0fa32b1cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000011900-95cc383c6d1d01e7967cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03r0-0003691600-2608430d4ebdcd7c402cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0229-0003691100-418c96145d1d6f04d8e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000011900-134506c18d94e4a087a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03k9-0003691600-a30e1e1c153022c74d01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0229-0003691100-dcf5ad66193bba345f84View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000010900-c9e6a88a4b1083f19d41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000022900-c22730aa7d46e7968fe6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0100319100-a50add63ef8555162f13View 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 IDHMDB0008961
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB026151
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52924917
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(16:1(9Z)/18:2(9Z,12Z)/0:0) → Cytidine monophosphate + PE(16:1(9Z)/18:2(9Z,12Z))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)/18:2(9Z,12Z)) → PE(16:1(9Z)/18:2(9Z,12Z)) + Carbon dioxidedetails