Showing metabocard for DG(20:1(11Z)/22:1(13Z)/0:0) (BMDB0007406)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:36:42 UTC
Update Date2020-05-21 16:28:00 UTC
BMDB IDBMDB0007406
Secondary Accession Numbers
  • BMDB07406
Metabolite Identification
Common NameDG(20:1(11Z)/22:1(13Z)/0:0)
DescriptionDG(20:1(11Z)/22:1(13Z)/0:0), also known as DAG(20:1/22:1) or diacylglycerol(20:1/22:1), belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2. Thus, DG(20:1(11Z)/22:1(13Z)/0:0) is considered to be a diradylglycerol lipid molecule. DG(20:1(11Z)/22:1(13Z)/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(20:1(11Z)/22:1(13Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(20:1(11Z)/22:1(13Z)/0:0) can be biosynthesized from PA(20:1(11Z)/22:1(13Z)) through its interaction with the enzyme phosphatidate phosphatase. Furthermore, DG(20:1(11Z)/22:1(13Z)/0:0) and docosadienoyl-CoA can be converted into TG(20:1(11Z)/22:1(13Z)/22:2(13Z,16Z)); which is mediated by the enzyme diacylglycerol O-acyltransferase. Furthermore, DG(20:1(11Z)/22:1(13Z)/0:0) can be biosynthesized from PA(20:1(11Z)/22:1(13Z)) through the action of the enzyme phosphatidate phosphatase. Finally, DG(20:1(11Z)/22:1(13Z)/0:0) and tetracosanoyl-CoA can be converted into TG(20:1(11Z)/22:1(13Z)/24:0); which is catalyzed by the enzyme diacylglycerol O-acyltransferase. In cattle, DG(20:1(11Z)/22:1(13Z)/0:0) is involved in a couple of metabolic pathways, which include de novo triacylglycerol biosynthesis TG(20:1(11Z)/22:1(13Z)/22:2(13Z,16Z)) pathway and de novo triacylglycerol biosynthesis TG(20:1(11Z)/22:1(13Z)/24:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DAG(20:1/22:1)HMDB
1-Eicosenoyl-2-erucoyl-sn-glycerolHMDB
DAG(42:2)HMDB
DiglycerideHMDB
Diacylglycerol(20:1/22:1)HMDB
DG(42:2)HMDB
DiacylglycerolHMDB
DG(20:1/22:1)HMDB
Diacylglycerol(42:2)HMDB
1-(11-Eicosenoyl)-2-(13Z-docosenoyl)-sn-glycerolHMDB
DG(20:1(11Z)/22:1(13Z)/0:0)Lipid Annotator
Chemical FormulaC45H84O5
Average Molecular Weight705.1455
Monoisotopic Molecular Weight704.631875798
IUPAC Name(2S)-1-hydroxy-3-[(11Z)-icos-11-enoyloxy]propan-2-yl (13Z)-docos-13-enoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H]\C(CCCCCCCC)=C(/[H])CCCCCCCCCCCC(=O)O[C@@]([H])(CO)COC(=O)CCCCCCCCC\C([H])=C(\[H])CCCCCCCC
InChI Identifier
InChI=1S/C45H84O5/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/h17-20,43,46H,3-16,21-42H2,1-2H3/b19-17-,20-18-/t43-/m0/s1
InChI KeyTXSPVVDGQJIPFG-ALXJKLDESA-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
logP10.74ALOGPS
logP15.72ChemAxon
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 Count42ChemAxon
Refractivity215.94 m³·mol⁻¹ChemAxon
Polarizability92.67 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, Positivesplash10-00di-0000000900-f57912e5a3115d4646feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014t-0009003100-ed6450d3613f5f52d018View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bb-0009000300-77999fb1251df0539e4fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000900-22a8e38c4a96cde10ac8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000000900-22a8e38c4a96cde10ac8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0150-0009600100-ce97e5dbcde58cb35030View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0129112600-4085718b7b5780e4a9ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06dl-0169000000-e0f2cc21a5b425579e74View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0597-6913000000-2cd5f8fd896caedc1264View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000000900-46bb7b8edeb864cb1e02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014t-0009003100-7159e798dcce034976a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bb-0009000300-e80280fd3254f006dc7bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-0009000300-aa24a8f5220131c7d267View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ap3-2019000100-31184bacac4329bdb91eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-2039000000-dbb0247218b0378083bfView 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 IDHMDB0007406
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543885
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(20:1(11Z)/22:1(13Z)/0:0) → Cytidine monophosphate + PE(20:1(11Z)/22:1(13Z))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(20:1(11Z)/22:1(13Z)/0:0) + Erucoyl-CoA → TG(20:1(11Z)/22:1(13Z)/22:1(13Z)) + Coenzyme Adetails
DG(20:1(11Z)/22:1(13Z)/0:0) + Clupanodonyl CoA → TG(20:1(11Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails