Showing metabocard for DG(20:2(11Z,14Z)/22:0/0:0)[iso2] (BMDB0062644)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-08-29 17:09:16 UTC
Update Date2020-06-04 19:40:31 UTC
BMDB IDBMDB0062644
Secondary Accession Numbers
  • BMDB62644
Metabolite Identification
Common NameDG(20:2(11Z,14Z)/22:0/0:0)[iso2]
DescriptionDG(20:2(11Z,14Z)/22:0/0:0), also known as diacylglycerol or DAG(20:2/22:0), 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(20:2(11Z,14Z)/22:0/0:0) is considered to be a diradylglycerol lipid molecule. DG(20:2(11Z,14Z)/22:0/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(20:2(11Z,14Z)/22:0/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(20:2(11Z,14Z)/22:0/0:0) can be biosynthesized from PA(20:2(11Z,14Z)/22:0); which is catalyzed by the enzyme phosphatidate phosphatase. In addition, DG(20:2(11Z,14Z)/22:0/0:0) and adrenoyl-CoA can be converted into TG(20:2(11Z,14Z)/22:0/22:4(7Z,10Z,13Z,16Z)); which is mediated by the enzyme diacylglycerol O-acyltransferase. In cattle, DG(20:2(11Z,14Z)/22:0/0:0) is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(20:2(11Z,14Z)/22:0/22:4(7Z,10Z,13Z,16Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2R)-1-Hydroxy-3-[(11Z,14Z)-icosa-11,14-dienoyloxy]propan-2-yl docosanoic acidGenerator
Chemical FormulaC45H84O5
Average Molecular Weight705.162
Monoisotopic Molecular Weight704.631875805
IUPAC Name(2R)-1-hydroxy-3-[(11Z,14Z)-icosa-11,14-dienoyloxy]propan-2-yl docosanoate
Traditional Name(2R)-1-hydroxy-3-[(11Z,14Z)-icosa-11,14-dienoyloxy]propan-2-yl docosanoate
CAS Registry NumberNot Available
SMILES
[H][C@@](CO)(COC(=O)CCCCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCCCCCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C45H84O5/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/h12,14,18,20,43,46H,3-11,13,15-17,19,21-42H2,1-2H3/b14-12-,20-18-/t43-/m1/s1
InChI KeyKVPLVJYCAJVIFI-RNLCRUPCSA-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
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
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
logP10.76ALOGPS
logP15.72ChemAxon
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
Refractivity215.94 m³·mol⁻¹ChemAxon
Polarizability94.65 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0avm-1039001200-3195f02fb934f1b8d09fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00r5-2079002000-96318cc6d3ed0b578dc6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002b-1092112000-05015601dbc46cfc27a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052r-0039000200-4206d0f927bf68c81729View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-1049000000-48a33334bd4854d55dcdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-3039000000-7ea6520c6d197f771a3fView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen Locations
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected and Quantified1.5 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDNot Available
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 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.