Showing metabocard for DG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/0:0) (BMDB0007458)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:37:45 UTC
Update Date2020-05-21 16:28:02 UTC
BMDB IDBMDB0007458
Secondary Accession Numbers
  • BMDB07458
Metabolite Identification
Common NameDG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/0:0)
DescriptionDG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/0:0), also known as dg(20:3(5z,8z,11z)/20:3(5z,8z,11z)/0:0) or DAG(20:3/20:3), belongs to the class of organic compounds known as 1,2-dg(20:3(5z,8z,11z)/20:3(5z,8z,11z)/0:0)s. These are dg(20:3(5z,8z,11z)/20:3(5z,8z,11z)/0:0)s containing a glycerol acylated at positions 1 and 2. DG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/0:0) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). DG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/0:0) can be biosynthesized from PA(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)) through the action of the enzyme phosphatidate phosphatase. Furthermore, DG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/0:0) and meadoyl-CoA can be converted into TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)); which is mediated by the enzyme dg(20:3(5z,8z,11z)/20:3(5z,8z,11z)/0:0) O-acyltransferase. Furthermore, DG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/0:0) can be biosynthesized from PA(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)); which is catalyzed by the enzyme phosphatidate phosphatase. Furthermore, DG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/0:0) and docosadienoyl-CoA can be converted into TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z)); which is mediated by the enzyme dg(20:3(5z,8z,11z)/20:3(5z,8z,11z)/0:0) O-acyltransferase. Furthermore, DG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/0:0) can be biosynthesized from PA(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)) through its interaction with the enzyme phosphatidate phosphatase. Finally, DG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/0:0) and tetracosanoyl-CoA can be converted into TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/24:0); which is mediated by the enzyme dg(20:3(5z,8z,11z)/20:3(5z,8z,11z)/0:0) O-acyltransferase. In cattle, DG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/0:0) is involved in a few metabolic pathways, which include de novo triacylglycerol biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)) pathway, de novo triacylglycerol biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z)) pathway, and de novo triacylglycerol biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/24:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2-Dimeadoyl-rac-glycerolHMDB
DAG(20:3/20:3)HMDB
DAG(20:3N9/20:3N9)HMDB
DAG(20:3W9/20:3W9)HMDB
DAG(40:6)HMDB
DG(20:3/20:3)HMDB
DG(20:3N9/20:3N9)HMDB
DG(20:3W9/20:3W9)HMDB
DG(40:6)HMDB
DiacylglycerolHMDB
Diacylglycerol(20:3/20:3)HMDB
Diacylglycerol(20:3n9/20:3n9)HMDB
Diacylglycerol(20:3W9/20:3W9)HMDB
Diacylglycerol(40:6)HMDB
DiglycerideHMDB
1,2-Di(5Z,8Z,11Z-eicosatrienoyl)-rac-glycerolHMDB
DG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/0:0)Lipid Annotator
Chemical FormulaC43H72O5
Average Molecular Weight669.0288
Monoisotopic Molecular Weight668.537975414
IUPAC Name(2S)-1-hydroxy-3-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propan-2-yl (5Z,8Z,11Z)-icosa-5,8,11-trienoate
Traditional Name1,2-dimeadoyl-rac-glycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCC\C=C/C\C=C/C\C=C/CCCCCCCC)OC(=O)CCC\C=C/C\C=C/C\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C43H72O5/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/h17-20,23-26,29-32,41,44H,3-16,21-22,27-28,33-40H2,1-2H3/b19-17-,20-18-,25-23-,26-24-,31-29-,32-30-/t41-/m0/s1
InChI KeyVIGULOPHPJPIAO-XIUQCZDVSA-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 DescriptorsNot Available
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
logP9.77ALOGPS
logP13.39ChemAxon
logS-7.8ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count36ChemAxon
Refractivity211.21 m³·mol⁻¹ChemAxon
Polarizability84.4 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, Positivesplash10-03di-4079272000-1452b4c04d21aa44603cView in MoNA
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, Positivesplash10-03y0-1049005000-50a192a99b2ab5fb44e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ds-3098332000-2ca0bf4a99e33cc66d7fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p2-2094451000-c9bbefef710580c85a3fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0cdr-0049003000-269e62259ed8f196f7f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-1049001000-bb15ddff44425fd8aa9fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3049000000-e839239f2f8d9f8da7aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000009000-d8fc180957e9e2b5f8d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000009000-d8fc180957e9e2b5f8d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0009001000-e43ff6d4c84f52f82f25View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1019008000-3997b8c167a291791e2dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-4029000000-301248d9b4704b632514View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-2029000000-80557a4300bf6e0add7aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1344039000-ffdc2e86a3822c4ad0feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-4096041000-706e189f2b6982ba773dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-2796010000-7a4769566d4e69890e45View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000009000-e2329eb25be3f42c3a5dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ik9-0008009000-08f6aa9139963f241f0cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dr-0008009000-a957edddd5db72d49b60View 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 IDHMDB0007458
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024651
KNApSAcK IDNot Available
Chemspider ID24766161
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53478253
PDB IDNot Available
ChEBI ID89786
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(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/0:0) → Cytidine monophosphate + PE(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))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(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/0:0) + Erucoyl-CoA → TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/22:1(13Z)) + Coenzyme Adetails
DG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/0:0) + Clupanodonyl CoA → TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails