Showing metabocard for DG(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) (BMDB0007382)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:36:14 UTC
Update Date2020-05-21 16:27:59 UTC
BMDB IDBMDB0007382
Secondary Accession Numbers
  • BMDB07382
Metabolite Identification
Common NameDG(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)
DescriptionDG(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)[iso2], also known as dg(20:0/22:6(4z,7z,10z,13z,16z,19z)/0:0)[iso2] or DAG(20:0/22:6), belongs to the class of organic compounds known as 1,2-dg(20:0/22:6(4z,7z,10z,13z,16z,19z)/0:0)[iso2]s. These are dg(20:0/22:6(4z,7z,10z,13z,16z,19z)/0:0)[iso2]s containing a glycerol acylated at positions 1 and 2. Thus, DG(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)[iso2] is considered to be a diradylglycerol lipid molecule. DG(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)[iso2] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, DG(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)[iso2] is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Arachidonyl-2-docosahexaenoyl-sn-glycerolHMDB
DAG(20:0/22:6)HMDB
DAG(20:0/22:6N3)HMDB
DAG(20:0/22:6W3)HMDB
DAG(42:6)HMDB
DG(20:0/22:6)HMDB
DG(20:0/22:6N3)HMDB
DG(20:0/22:6W3)HMDB
DG(42:6)HMDB
DiacylglycerolHMDB
Diacylglycerol(20:0/22:6)HMDB
Diacylglycerol(20:0/22:6n3)HMDB
Diacylglycerol(20:0/22:6W3)HMDB
Diacylglycerol(42:6)HMDB
DiglycerideHMDB
1-Eicosanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycerolHMDB
DG(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)Lipid Annotator
Chemical FormulaC45H76O5
Average Molecular Weight697.0819
Monoisotopic Molecular Weight696.569275542
IUPAC Name(2S)-1-hydroxy-3-(icosanoyloxy)propan-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)CCCCCCCCCCCCCCCCCCC)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/C45H76O5/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-36-38-40-45(48)50-43(41-46)42-49-44(47)39-37-35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h5,7,11,13,17,19,22,24,28,30,34,36,43,46H,3-4,6,8-10,12,14-16,18,20-21,23,25-27,29,31-33,35,37-42H2,1-2H3/b7-5-,13-11-,19-17-,24-22-,30-28-,36-34-/t43-/m0/s1
InChI KeyWKXRCUYDMVQYFL-PZJJUGDGSA-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
logP10.18ALOGPS
logP14.28ChemAxon
logS-7.9ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count38ChemAxon
Refractivity220.41 m³·mol⁻¹ChemAxon
Polarizability87.88 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, Positivesplash10-03di-0000000900-4d1a8fb2902d0b1a9641View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0179-0009003000-9659dbe0083fc4047bd4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02tr-0009001300-96f41205e7c1304c94c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000000900-8a1c6226c0719bd2dacdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000000900-8a1c6226c0719bd2dacdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4o-0009600100-a1fe2caf0c575e58469cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1038029000-b3860da881a926940783View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1049011000-7ed00547a01a0c9b93baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03e9-1139000000-db26d0b3317dfc607abcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000900-0e123f184b57ffebfcd6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0179-0009003000-64ffdb4fc457ae349d85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02tr-0009001300-e9b5bf9ee6ee393c3011View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1007009000-8cff82827c2fbac49db3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-3019001000-12bfffbb8ddbb9a9528cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fu-3049000000-485cc94f6d2c3ca6f2b4View 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 IDHMDB0007382
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024575
KNApSAcK IDNot Available
Chemspider ID7822872
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543922
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(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) → Cytidine monophosphate + PE(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))details
Enzyme Details
2. Diacylglycerol O-acyltransferase 1
General function:
Not Available
Specific function:
Catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. In contrast to DGAT2 it is not essential for survival. May be involved in VLDL (very low density lipoprotein) assembly. Functions as the major acyl-CoA retinol acyltransferase (ARAT) in the skin, where it acts to maintain retinoid homeostasis and prevent retinoid toxicity leading to skin and hair disorders. In liver, plays a role in esterifying exogenous fatty acids to glycerol.
Gene Name:
DGAT1
Uniprot ID:
Q8MK44
Molecular weight:
55602.0
Reactions
DG(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) + Tetracosanoyl-CoA → TG(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0) + Coenzyme Adetails