Showing metabocard for DG(20:0/20:0/0:0) (BMDB0007368)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:35:57 UTC
Update Date2020-05-21 16:27:58 UTC
BMDB IDBMDB0007368
Secondary Accession Numbers
  • BMDB07368
Metabolite Identification
Common NameDG(20:0/20:0/0:0)
DescriptionDG(20:0/20:0/0:0), also known as DAG(20:0/20:0) or dg(20:0/20:0/0:0), belongs to the class of organic compounds known as 1,2-dg(20:0/20:0/0:0)s. These are dg(20:0/20:0/0:0)s containing a glycerol acylated at positions 1 and 2. Thus, DG(20:0/20:0/0:0) is considered to be a diradylglycerol lipid molecule. DG(20:0/20:0/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(20:0/20:0/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(20:0/20:0/0:0) can be biosynthesized from PA(20:0/20:0); which is mediated by the enzyme phosphatidate phosphatase. In addition, DG(20:0/20:0/0:0) and eicosanoyl-CoA can be converted into TG(20:0/20:0/20:0); which is catalyzed by the enzyme dg(20:0/20:0/0:0) O-acyltransferase. In cattle, DG(20:0/20:0/0:0) is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(20:0/20:0/20:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DG(40:0)HMDB
DAG(40:0)HMDB
1,2-Diarachidonyl-rac-glycerolHMDB
DiglycerideHMDB
Diacylglycerol(20:0/20:0)HMDB
DAG(20:0/20:0)HMDB
DiacylglycerolHMDB
DG(20:0/20:0)HMDB
Diacylglycerol(40:0)HMDB
1,2-Dieicosanoyl-rac-glycerolHMDB
DG(20:0/20:0/0:0)Lipid Annotator
Chemical FormulaC43H84O5
Average Molecular Weight681.1241
Monoisotopic Molecular Weight680.631875798
IUPAC Name(2S)-1-hydroxy-3-(icosanoyloxy)propan-2-yl icosanoate
Traditional Name1,2-dieicosanoyl-sn-glycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C43H84O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-42(45)47-40-41(39-44)48-43(46)38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h41,44H,3-40H2,1-2H3/t41-/m0/s1
InChI KeyAGUTXIBMYVFOMK-RWYGWLOXSA-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
logP10.62ALOGPS
logP15.56ChemAxon
logS-7.7ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count42ChemAxon
Refractivity204.51 m³·mol⁻¹ChemAxon
Polarizability92.48 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, Positivesplash10-0002-0000009000-a996981cc7eab232c7d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02t9-0009009000-cfcfe7c1186acc2f7717View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-0009009000-7f96576c37486f595556View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ls-1049008000-1b82b6c4c5c338e149b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0292-2198003000-119f7667f36a107cdf0cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9777000000-88c1d57d322a1827b4aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1009007000-f9eca941a2efcca2e135View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-1029000000-1666fd8a65984321be39View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dl-1049000000-7776b7a72b068794290dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000009000-f14e65ae75b5f7d9ae8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02t9-0008009000-969afe07eb970f0aea68View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-0008009000-019455c2bf5bbbb7e16dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000900-f13f4fb2a7eb01fe42d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000000900-f13f4fb2a7eb01fe42d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0009000100-801c6a81480730dbcc60View 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 IDHMDB0007368
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024561
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543782
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(20:0/20:0/0:0) → Cytidine monophosphate + PE(20:0/20:0)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(20:0/20:0/0:0) + Eicosanoyl-CoA → TG(20:0/20:0/20:0) + Coenzyme Adetails
DG(20:0/20:0/0:0) + Gondoyl-CoA → TG(20:0/20:0/20:1(11Z)) + Coenzyme Adetails
DG(20:0/20:0/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(20:0/20:0/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(20:0/20:0/0:0) + Docosanoyl-CoA → TG(20:0/20:0/22:0) + Coenzyme Adetails
DG(20:0/20:0/0:0) + Erucoyl-CoA → TG(20:0/20:0/22:1(13Z)) + Coenzyme Adetails
DG(20:0/20:0/0:0) + Heptadecanoyl CoA → TG(20:0/20:0/17:0) + Coenzyme Adetails
DG(20:0/20:0/0:0) + Tridecanoyl-CoA → TG(20:0/20:0/13:0) + Coenzyme Adetails
DG(20:0/20:0/0:0) + Lauroyl-CoA → TG(20:0/20:0/12:0) + Coenzyme Adetails