Showing metabocard for DG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) (BMDB0007788)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:44:25 UTC
Update Date2020-05-21 16:26:50 UTC
BMDB IDBMDB0007788
Secondary Accession Numbers
  • BMDB07788
Metabolite Identification
Common NameDG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)
DescriptionDG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0), also known as DAG(22:6/22:6) or DAG(22:6OMEGA3/22:6OMEGA3), belongs to the class of organic compounds known as 1,2-dg(22:6(4z,7z,10z,13z,16z,19z)/22:6(4z,7z,10z,13z,16z,19z)/0:0)s. These are dg(22:6(4z,7z,10z,13z,16z,19z)/22:6(4z,7z,10z,13z,16z,19z)/0:0)s containing a glycerol acylated at positions 1 and 2. Thus, DG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) is considered to be a diradylglycerol lipid molecule. DG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, CDP-Ethanolamine and DG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) can be converted into cytidine monophosphate and PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Furthermore, CDP-Choline and DG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) can be converted into cytidine monophosphate and PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Furthermore, DG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) can be biosynthesized from PA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)); which is mediated by the enzyme phosphatidate phosphatase. Finally, DG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) and nervonoyl-CoA can be converted into TG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z)); which is mediated by the enzyme dg(22:6(4z,7z,10z,13z,16z,19z)/22:6(4z,7z,10z,13z,16z,19z)/0:0) O-acyltransferase. In cattle, DG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) pathway and de novo triacylglycerol biosynthesis TG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2-Di-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycerolChEBI
1,2-Didocosahexaenoyl-sn-glycerolChEBI
DAG(22:6/22:6)ChEBI
DAG(22:6N3/22:6N3)ChEBI
DAG(22:6OMEGA3/22:6OMEGA3)ChEBI
DAG(44:12)ChEBI
DG(22:6/22:6)ChEBI
DG(22:6/22:6/0:0)ChEBI
DG(22:6N3/22:6N3)ChEBI
DG(22:6OMEGA3/22:6OMEGA3)ChEBI
DG(44:12)ChEBI
Diacylglycerol(22:6/22:6)ChEBI
Diacylglycerol(22:6n3/22:6n3)ChEBI
Diacylglycerol(22:6omega3/22:6omega3)ChEBI
Diacylglycerol(44:12)ChEBI
1,2-Didocosahexaenoyl-rac-glycerolHMDB
DAG(22:6W3/22:6W3)HMDB
DG(22:6W3/22:6W3)HMDB
DiacylglycerolHMDB
Diacylglycerol(22:6W3/22:6W3)HMDB
DiglycerideHMDB
1,2-Di(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-rac-glycerolHMDB
DG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)Lipid Annotator
Chemical FormulaC47H68O5
Average Molecular Weight713.0398
Monoisotopic Molecular Weight712.506675286
IUPAC Name(2S)-1-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-hydroxypropan-2-yl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C47H68O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-39-41-46(49)51-44-45(43-48)52-47(50)42-40-38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h5-8,11-14,17-20,23-26,29-32,35-38,45,48H,3-4,9-10,15-16,21-22,27-28,33-34,39-44H2,1-2H3/b7-5-,8-6-,13-11-,14-12-,19-17-,20-18-,25-23-,26-24-,31-29-,32-30-,37-35-,38-36-/t45-/m0/s1
InChI KeyXIAZEYRSKHAPND-CYDJSWNTSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerolipids
Sub ClassDiradylglycerols
Direct Parent1,2-diacylglycerols
Alternative Parents
Substituents
  • 1,2-acyl-sn-glycerol
  • Fatty acid ester
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • 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
  • 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
logP12.99ChemAxon
logS-7.3ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count34ChemAxon
Refractivity236.31 m³·mol⁻¹ChemAxon
Polarizability85.13 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_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dr-1009112200-0a7f8e5f7335220c501bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03y0-2039343000-e3a0ecfe78043d2f6ba9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02t9-3079365000-f80ce3b2b9df91665bbbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-06w9-0009100200-1118aa29877759f7e71bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-1009100000-41de257f3296e4a6e18bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-2019000000-eeab2e58dcb175c3c68fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ik9-1004209300-7f039f1ba69763059f4aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2019013000-3cf90cb609d733464b64View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01u0-0289012000-bf30012cf6a6b8cd1598View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000900-0c422b3a9482ba4ce7edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000000900-0c422b3a9482ba4ce7edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0001900100-2efccd1fec7e3c4a8d89View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000900-4f4d9a1266aaf0b49f39View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000j-0009006300-8f49bbcb1e3b93a4db1bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0019-0009001700-d79153a6facb6caefb43View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03fr-0009100500-11345a326c97c722d608View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-5009000000-1ab27c2be3a3d02a9325View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-2039000000-b2cd04a371f19759a4b1View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0007788
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024981
KNApSAcK IDNot Available
Chemspider ID7822921
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543971
PDB IDNot Available
ChEBI ID82925
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(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) → Cytidine monophosphate + PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))details