Showing metabocard for DG(22:2(13Z,16Z)/22:2(13Z,16Z)/0:0) (BMDB0007668)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:42:00 UTC
Update Date2020-05-21 16:28:07 UTC
BMDB IDBMDB0007668
Secondary Accession Numbers
  • BMDB07668
Metabolite Identification
Common NameDG(22:2(13Z,16Z)/22:2(13Z,16Z)/0:0)
DescriptionDG(22:2(13Z,16Z)/22:2(13Z,16Z)/0:0), also known as dg(22:2(13z,16z)/22:2(13z,16z)/0:0) or DAG(22:2/22:2), belongs to the class of organic compounds known as 1,2-dg(22:2(13z,16z)/22:2(13z,16z)/0:0)s. These are dg(22:2(13z,16z)/22:2(13z,16z)/0:0)s containing a glycerol acylated at positions 1 and 2. Thus, DG(22:2(13Z,16Z)/22:2(13Z,16Z)/0:0) is considered to be a diradylglycerol lipid molecule. DG(22:2(13Z,16Z)/22:2(13Z,16Z)/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(22:2(13Z,16Z)/22:2(13Z,16Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(22:2(13Z,16Z)/22:2(13Z,16Z)/0:0) can be biosynthesized from PA(22:2(13Z,16Z)/22:2(13Z,16Z)); which is mediated by the enzyme phosphatidate phosphatase. Furthermore, DG(22:2(13Z,16Z)/22:2(13Z,16Z)/0:0) and adrenoyl-CoA can be converted into TG(22:2(13Z,16Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)); which is catalyzed by the enzyme dg(22:2(13z,16z)/22:2(13z,16z)/0:0) O-acyltransferase. Furthermore, DG(22:2(13Z,16Z)/22:2(13Z,16Z)/0:0) can be biosynthesized from PA(22:2(13Z,16Z)/22:2(13Z,16Z)) through its interaction with the enzyme phosphatidate phosphatase. Finally, DG(22:2(13Z,16Z)/22:2(13Z,16Z)/0:0) and nervonoyl-CoA can be converted into TG(22:2(13Z,16Z)/22:2(13Z,16Z)/24:1(15Z)) through its interaction with the enzyme dg(22:2(13z,16z)/22:2(13z,16z)/0:0) O-acyltransferase. In cattle, DG(22:2(13Z,16Z)/22:2(13Z,16Z)/0:0) is involved in a couple of metabolic pathways, which include de novo triacylglycerol biosynthesis TG(22:2(13Z,16Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)) pathway and de novo triacylglycerol biosynthesis TG(22:2(13Z,16Z)/22:2(13Z,16Z)/24:1(15Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2-Didocosadienoyl-rac-glycerolHMDB
DAG(22:2/22:2)HMDB
DAG(22:2N6/22:2N6)HMDB
DAG(22:2W6/22:2W6)HMDB
DAG(44:4)HMDB
DG(22:2/22:2)HMDB
DG(22:2N6/22:2N6)HMDB
DG(22:2W6/22:2W6)HMDB
DG(44:4)HMDB
DiacylglycerolHMDB
Diacylglycerol(22:2/22:2)HMDB
Diacylglycerol(22:2n6/22:2n6)HMDB
Diacylglycerol(22:2W6/22:2W6)HMDB
Diacylglycerol(44:4)HMDB
DiglycerideHMDB
1,2-Di(13Z,16Z-docosadienoyl)-rac-glycerolHMDB
DG(22:2(13Z,16Z)/22:2(13Z,16Z)/0:0)Lipid Annotator
Chemical FormulaC47H84O5
Average Molecular Weight729.1669
Monoisotopic Molecular Weight728.631875798
IUPAC Name(2S)-1-[(13Z,16Z)-docosa-13,16-dienoyloxy]-3-hydroxypropan-2-yl (13Z,16Z)-docosa-13,16-dienoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCCCCCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C47H84O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-39-41-46(49)51-44-45(43-48)52-47(50)42-40-38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h11-14,17-20,45,48H,3-10,15-16,21-44H2,1-2H3/b13-11-,14-12-,19-17-,20-18-/t45-/m0/s1
InChI KeySCVNSJLHAHBZQT-TWWVEEIUSA-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
logP10.69ALOGPS
logP15.89ChemAxon
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
Refractivity227.38 m³·mol⁻¹ChemAxon
Polarizability95.09 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, Positivesplash10-0002-0000000900-87fa0b8a80e34f648f7aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-0009000900-97998851f40ba73aae78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-0009000900-b8fe1cdceb72a5b86958View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000900-3d176dd72e2a86160706View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000000900-3d176dd72e2a86160706View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0001900100-788ff255a6bbe5cd3481View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-056r-2007400900-3eb4efbdc7405ea2492cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ri-4009000000-76fbdf165ae8ecf8d887View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-2009000000-96b628f61dfc1638618dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-4337203900-5f8659b13fce2a20443cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02tc-1119100100-e32a0807e66b183dc973View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-3319100000-976d25e35317db663863View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000000900-3079377e63427db38714View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-0008000900-ac416f78eb11615e6376View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-0008000900-5cc4e2629baf10a32771View 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 IDHMDB0007668
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024861
KNApSAcK IDNot Available
Chemspider ID7822906
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543956
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(22:2(13Z,16Z)/22:2(13Z,16Z)/0:0) → Cytidine monophosphate + PE(22:2(13Z,16Z)/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(22:2(13Z,16Z)/22:2(13Z,16Z)/0:0) + Clupanodonyl CoA → TG(22:2(13Z,16Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails