Showing metabocard for DG(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) (BMDB0007670)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:42:03 UTC
Update Date2020-05-21 16:28:07 UTC
BMDB IDBMDB0007670
Secondary Accession Numbers
  • BMDB07670
Metabolite Identification
Common NameDG(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0)
DescriptionDG(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0), also known as DAG(22:2/22:5) or dg(22:2(13z,16z)/22:5(4z,7z,10z,13z,16z)/0:0), belongs to the class of organic compounds known as 1,2-dg(22:2(13z,16z)/22:5(4z,7z,10z,13z,16z)/0:0)s. These are dg(22:2(13z,16z)/22:5(4z,7z,10z,13z,16z)/0:0)s containing a glycerol acylated at positions 1 and 2. DG(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). DG(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) can be biosynthesized from PA(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)); which is catalyzed by the enzyme phosphatidate phosphatase. In addition, DG(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) and osbondoyl-CoA can be converted into TG(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) through the action of the enzyme dg(22:2(13z,16z)/22:5(4z,7z,10z,13z,16z)/0:0) O-acyltransferase. In cattle, DG(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DG(44:7)HMDB
DAG(22:2/22:5)HMDB
DiglycerideHMDB
1-Docosadienoyl-2-osbondoyl-sn-glycerolHMDB
Diacylglycerol(22:2/22:5)HMDB
DiacylglycerolHMDB
DAG(44:7)HMDB
Diacylglycerol(44:7)HMDB
DG(22:2/22:5)HMDB
1-(13Z,16Z-Docosadienoyl)-2-(4Z,7Z,10Z,13Z,16Z-docosapentaenoyl)-sn-glycerolHMDB
DG(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0)Lipid Annotator
Chemical FormulaC47H78O5
Average Molecular Weight723.1192
Monoisotopic Molecular Weight722.584925606
IUPAC Name(2S)-1-[(13Z,16Z)-docosa-13,16-dienoyloxy]-3-hydroxypropan-2-yl (4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C47H78O5/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/h11-14,17-20,24,26,30,32,36,38,45,48H,3-10,15-16,21-23,25,27-29,31,33-35,37,39-44H2,1-2H3/b13-11-,14-12-,19-17-,20-18-,26-24-,32-30-,38-36-/t45-/m0/s1
InChI KeyWQCGJEYJCWPUNB-JQABRDIGSA-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
logP9.99ALOGPS
logP14.8ChemAxon
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
Refractivity230.73 m³·mol⁻¹ChemAxon
Polarizability91.23 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, Positivesplash10-0006-0000000900-9ad362d348b230114d67View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052o-0009000400-325b91481524ed88e820View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-0009000400-3076d96e458eae5d40bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1008300900-db0aa125d70f4e00db37View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-3009000000-20f5b1b904a942fa06faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05n0-3109000000-a7008149152fb70a7e21View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-074r-4139223800-d627369e4b4e54db7aecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03xr-1009000000-99a2517077771b4f8ab9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0219000000-6ab0f1888e4618c381dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000000900-23c6224e656e3a1fccebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052o-0009000400-1b00c8ad024657df3811View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-0009000400-73b4e1deeb4873adec9fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000000900-deaa9c89a27cd482add9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000000900-deaa9c89a27cd482add9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-0001900000-3cc6d3024f7adda119cfView 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 IDHMDB0007670
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024863
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53478428
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. 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)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) + Clupanodonyl CoA → TG(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails