Showing metabocard for DG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/0:0) (BMDB0007465)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:37:53 UTC
Update Date2020-05-21 16:28:02 UTC
BMDB IDBMDB0007465
Secondary Accession Numbers
  • BMDB07465
Metabolite Identification
Common NameDG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/0:0)
DescriptionDG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/0:0), also known as DAG(20:3/22:2) or dg(20:3(5z,8z,11z)/22:2(13z,16z)/0:0), belongs to the class of organic compounds known as 1,2-dg(20:3(5z,8z,11z)/22:2(13z,16z)/0:0)s. These are dg(20:3(5z,8z,11z)/22:2(13z,16z)/0:0)s containing a glycerol acylated at positions 1 and 2. DG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/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)/22:2(13Z,16Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/0:0) can be biosynthesized from PA(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)) through the action of the enzyme phosphatidate phosphatase. In addition, DG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/0:0) and nervonoyl-CoA can be converted into TG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/24:1(15Z)) through its interaction with the enzyme dg(20:3(5z,8z,11z)/22:2(13z,16z)/0:0) O-acyltransferase. In cattle, DG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/0:0) is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/24:1(15Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DAG(20:3/22:2)HMDB
1-Meadoyl-2-docosadienoyl-sn-glycerolHMDB
DG(20:3/22:2)HMDB
DiglycerideHMDB
Diacylglycerol(42:5)HMDB
DAG(42:5)HMDB
DiacylglycerolHMDB
Diacylglycerol(20:3/22:2)HMDB
1-(5Z,8Z,11Z-Eicosatrienoyl)-2-(13Z,16Z-docosadienoyl)-sn-glycerolHMDB
DG(42:5)HMDB
DG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/0:0)Lipid Annotator
Chemical FormulaC45H78O5
Average Molecular Weight699.0978
Monoisotopic Molecular Weight698.584925606
IUPAC Name(2S)-1-hydroxy-3-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propan-2-yl (13Z,16Z)-docosa-13,16-dienoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCC\C=C/C\C=C/C\C=C/CCCCCCCC)OC(=O)CCCCCCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C45H78O5/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/h11,13,17-20,25,27,31,33,43,46H,3-10,12,14-16,21-24,26,28-30,32,34-42H2,1-2H3/b13-11-,19-17-,20-18-,27-25-,33-31-/t43-/m0/s1
InChI KeyKYBNFHHRRWYEHE-NMWOAREWSA-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
logP10.37ALOGPS
logP14.64ChemAxon
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 Count39ChemAxon
Refractivity219.29 m³·mol⁻¹ChemAxon
Polarizability89.85 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, Positivesplash10-014i-0000000900-106fba633af2f7bac685View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ef-0009003000-d5dfd43ab72ad7f6eb53View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03xx-0009001300-fdd963078db977f3039eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00l2-2249038000-c956798d74a941182a6aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1039001000-26c7b6120986546b0f73View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-1639000000-c062d420bcde0719a322View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000000900-05421be3ec5289cbf5d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000000900-05421be3ec5289cbf5d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0150-0009600100-fc378a84060dc02baa84View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-2009107000-5fa2d1fb248fe70eda7cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0abi-4019000000-9fd77fdaa6774b685666View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3019000000-a00dbd59eac6c28fd74cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000000900-9de81be7e33732c423a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ef-0009003000-315545d9a360b7d42997View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03xx-0009001300-120019c281dea139f478View 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 IDHMDB0007465
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 Compound53478260
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(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/0:0) → Cytidine monophosphate + PE(20:3(5Z,8Z,11Z)/22:2(13Z,16Z))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)/22:2(13Z,16Z)/0:0) + Clupanodonyl CoA → TG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails