Showing metabocard for DG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/0:0) (BMDB0007429)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:37:10 UTC
Update Date2020-05-21 16:28:01 UTC
BMDB IDBMDB0007429
Secondary Accession Numbers
  • BMDB07429
Metabolite Identification
Common NameDG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/0:0)
DescriptionDG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/0:0), also known as dg(20:2(11z,14z)/20:3(5z,8z,11z)/0:0) or DAG(20:2/20:3), belongs to the class of organic compounds known as 1,2-dg(20:2(11z,14z)/20:3(5z,8z,11z)/0:0)s. These are dg(20:2(11z,14z)/20:3(5z,8z,11z)/0:0)s containing a glycerol acylated at positions 1 and 2. DG(20:2(11Z,14Z)/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(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/0:0) can be biosynthesized from PA(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)); which is catalyzed by the enzyme phosphatidate phosphatase. Furthermore, DG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/0:0) and erucoyl-CoA can be converted into TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/22:1(13Z)); which is mediated by the enzyme dg(20:2(11z,14z)/20:3(5z,8z,11z)/0:0) O-acyltransferase. Furthermore, DG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/0:0) can be biosynthesized from PA(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)); which is mediated by the enzyme phosphatidate phosphatase. Furthermore, DG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/0:0) and adrenoyl-CoA can be converted into TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z)); which is catalyzed by the enzyme dg(20:2(11z,14z)/20:3(5z,8z,11z)/0:0) O-acyltransferase. Furthermore, DG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/0:0) can be biosynthesized from PA(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)); which is mediated by the enzyme phosphatidate phosphatase. Finally, DG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/0:0) and nervonoyl-CoA can be converted into TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/24:1(15Z)); which is catalyzed by the enzyme dg(20:2(11z,14z)/20:3(5z,8z,11z)/0:0) O-acyltransferase. In cattle, DG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/0:0) is involved in a few metabolic pathways, which include de novo triacylglycerol biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/22:1(13Z)) pathway, de novo triacylglycerol biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z)) pathway, and de novo triacylglycerol biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/24:1(15Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Eicosadienoyl-2-meadoyl-sn-glycerolHMDB
DAG(20:2/20:3)HMDB
DAG(20:2N6/20:3N9)HMDB
DAG(20:2W6/20:3W9)HMDB
DAG(40:5)HMDB
DG(20:2/20:3)HMDB
DG(20:2N6/20:3N9)HMDB
DG(20:2W6/20:3W9)HMDB
DG(40:5)HMDB
DiacylglycerolHMDB
Diacylglycerol(20:2/20:3)HMDB
Diacylglycerol(20:2n6/20:3n9)HMDB
Diacylglycerol(20:2W6/20:3W9)HMDB
Diacylglycerol(40:5)HMDB
DiglycerideHMDB
1-(11Z,14Z-Eicosadienoyl)-2-(5Z,8Z,11Z-eicosatrienoyl)-sn-glycerolHMDB
DG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/0:0)Lipid Annotator
Chemical FormulaC43H74O5
Average Molecular Weight671.0447
Monoisotopic Molecular Weight670.553625478
IUPAC Name(2S)-1-hydroxy-3-[(11Z,14Z)-icosa-11,14-dienoyloxy]propan-2-yl (5Z,8Z,11Z)-icosa-5,8,11-trienoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCC\C=C/C\C=C/C\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C43H74O5/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/h11,13,17-20,24,26,30,32,41,44H,3-10,12,14-16,21-23,25,27-29,31,33-40H2,1-2H3/b13-11-,19-17-,20-18-,26-24-,32-30-/t41-/m0/s1
InChI KeySPGHLBKMJHHORH-XASTUVSNSA-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
logP10.12ALOGPS
logP13.75ChemAxon
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 Count37ChemAxon
Refractivity210.09 m³·mol⁻¹ChemAxon
Polarizability85.5 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, Positivesplash10-000i-0000009000-952711fd2112e55cd8a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0jor-0009004000-74afbbbbe120f85cf485View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-04i9-0009004000-74cc7c1ba5e9f91f9fccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-4254049000-69b0315484a73f3fce95View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1194021000-0cd047b5cb5cfa2eeadeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053i-3389100000-9f399608e1c722d13282View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-067i-1019005000-f48f8362a730d95f80c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-4039000000-ff7924e4273c48a188aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-2039000000-bbee1983581bbea57fcaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000009000-d863793907e0818673abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000009000-d863793907e0818673abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0009000000-43d8527e17a35a581fe1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000009000-8c89de08aef23f3e4e34View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0jor-0009004000-1ff18a9dfd27ade4aeb9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-04i9-0009004000-b626cba25b48fb5864afView 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 IDHMDB0007429
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024622
KNApSAcK IDNot Available
Chemspider ID24766141
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53478233
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(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/0:0) → Cytidine monophosphate + PE(20:2(11Z,14Z)/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(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(20:2n6/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/0:0) + Clupanodonyl CoA → TG(20:2n6/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails