Showing metabocard for DG(22:0/22:0/0:0) (BMDB0007608)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:40:46 UTC
Update Date2020-05-21 16:28:05 UTC
BMDB IDBMDB0007608
Secondary Accession Numbers
  • BMDB07608
Metabolite Identification
Common NameDG(22:0/22:0/0:0)
DescriptionDG(22:0/22:0/0:0), also known as DG(22:0/22:0) or dg(22:0/22:0/0:0), belongs to the class of organic compounds known as 1,2-dg(22:0/22:0/0:0)s. These are dg(22:0/22:0/0:0)s containing a glycerol acylated at positions 1 and 2. Thus, DG(22:0/22:0/0:0) is considered to be a diradylglycerol lipid molecule. DG(22:0/22:0/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(22:0/22:0/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(22:0/22:0/0:0) can be biosynthesized from PA(22:0/22:0); which is mediated by the enzyme phosphatidate phosphatase. In addition, DG(22:0/22:0/0:0) and docosanoyl-CoA can be converted into TG(22:0/22:0/22:0) through the action of the enzyme dg(22:0/22:0/0:0) O-acyltransferase. In cattle, DG(22:0/22:0/0:0) is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(22:0/22:0/22:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DG(22:0/22:0)HMDB
Diacylglycerol(44:0)HMDB
DAG(44:0)HMDB
DG(44:0)HMDB
DiglycerideHMDB
Diacylglycerol(22:0/22:0)HMDB
DiacylglycerolHMDB
1,2-Dibehenoyl-rac-glycerolHMDB
1,2-Didocosanoyl-rac-glycerolHMDB
DAG(22:0/22:0)HMDB
DG(22:0/22:0/0:0)Lipid Annotator
Chemical FormulaC47H92O5
Average Molecular Weight737.2304
Monoisotopic Molecular Weight736.694476054
IUPAC Name(2S)-1-(docosanoyloxy)-3-hydroxypropan-2-yl docosanoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C47H92O5/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/h45,48H,3-44H2,1-2H3/t45-/m0/s1
InChI KeyGNWCZBXSKIIURR-GWHBCOKCSA-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
logP10.79ALOGPS
logP17.34ChemAxon
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 Count46ChemAxon
Refractivity222.91 m³·mol⁻¹ChemAxon
Polarizability101.12 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, Positivesplash10-0udi-0000000900-471203bec85cd15112fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-0009000900-fead69d10c2fbcd099c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6t-0009000900-7df3e603928b5082b0ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000900-a2748a9f97c9302a930fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-0008000900-e4d816dd5e0e9d2f9d31View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6t-0008000900-f50fd5f75d6a0c79c7c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000900-18f8c50dd7f77c625b40View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000000900-18f8c50dd7f77c625b40View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0001900100-f23e752164d5b79c15eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00rj-1009100700-9a122489d0822b3e358aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dj-1119000200-aecb16b97332634bb5a0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dj-6409000000-880038e102f17f37c30dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1006300900-0f747e8417d239c24af0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-1009000000-e1746df5a41e53f4ce72View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0079-0009000000-971c9938e107ab8035e5View 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 IDHMDB0007608
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024801
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543923
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(22:0/22:0/0:0) → Cytidine monophosphate + PE(22:0/22:0)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(22:0/22:0/0:0) + Docosanoyl-CoA → TG(22:0/22:0/22:0) + Coenzyme Adetails
DG(22:0/22:0/0:0) + Erucoyl-CoA → TG(22:0/22:0/22:1(13Z)) + Coenzyme Adetails
DG(22:0/22:0/0:0) + Clupanodonyl CoA → TG(22:0/22:0/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails
DG(22:0/22:0/0:0) + Tetracosanoyl-CoA → TG(22:0/22:0/24:0) + Coenzyme Adetails
DG(22:0/22:0/0:0) + Tridecanoyl-CoA → TG(22:0/22:0/13:0) + Coenzyme Adetails
DG(22:0/22:0/0:0) + Lauroyl-CoA → TG(22:0/22:0/12:0) + Coenzyme Adetails
DG(22:0/22:0/0:0) + Heptadecanoyl CoA → TG(22:0/22:0/17:0) + Coenzyme Adetails