Showing metabocard for DG(20:1(11Z)/22:0/0:0)[iso2] (BMDB0062642)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-08-29 17:09:14 UTC
Update Date2020-06-04 19:25:55 UTC
MCDB ID BMDB0062642
Secondary Accession Numbers
  • BMDB62642
Metabolite Identification
Common NameDG(20:1(11Z)/22:0/0:0)[iso2]
DescriptionDG(20:1(11Z)/22:0/0:0), also known as diacylglycerol or DAG(20:1/22:0), belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2. Thus, DG(20:1(11Z)/22:0/0:0) is considered to be a diradylglycerol lipid molecule. DG(20:1(11Z)/22:0/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(20:1(11Z)/22:0/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(20:1(11Z)/22:0/0:0) can be biosynthesized from PA(20:1(11Z)/22:0) through its interaction with the enzyme phosphatidate phosphatase. Furthermore, DG(20:1(11Z)/22:0/0:0) and adrenoyl-CoA can be converted into TG(20:1(11Z)/22:0/22:4(7Z,10Z,13Z,16Z)); which is mediated by the enzyme diacylglycerol O-acyltransferase. Finally, CDP-Ethanolamine and DG(20:1(11Z)/22:0/0:0) can be converted into cytidine monophosphate and PE(20:1(11Z)/22:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. In cattle, DG(20:1(11Z)/22:0/0:0) is involved in a couple of metabolic pathways, which include de novo triacylglycerol biosynthesis TG(20:1(11Z)/22:0/22:4(7Z,10Z,13Z,16Z)) pathway and phosphatidylethanolamine biosynthesis pe(20:1(11Z)/22:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC45H86O5
Average Molecular Weight707.178
Monoisotopic Molecular Weight706.647525869
IUPAC Name(2R)-1-hydroxy-3-[(11Z)-icos-11-enoyloxy]propan-2-yl docosanoate
Traditional Name(2R)-1-hydroxy-3-[(11Z)-icos-11-enoyloxy]propan-2-yl docosanoate
CAS Registry NumberNot Available
SMILES
[H][C@@](CO)(COC(=O)CCCCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C45H86O5/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/h18,20,43,46H,3-17,19,21-42H2,1-2H3/b20-18-/t43-/m1/s1
InChI KeyKKUJWTOLSKTBLP-KAKKGSANSA-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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP10.77ALOGPS
logP16.09ChemAxon
logS-7.7ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count43ChemAxon
Refractivity214.83 m³·mol⁻¹ChemAxon
Polarizability95.91 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot Available2022-08-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02ft-0009200100-3d5e184ec156ff1541312016-09-19View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.16 +/- 0.01 uM details
Detected and Quantified0.26 +/- 0.01 uM details
Detected and Quantified0.33 +/- 0.02 uM details
Detected and Quantified0.12 +/- 0.01 uM details
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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 CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.