Showing metabocard for DG(20:1(11Z)/22:0/0:0) (BMDB0007405)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:36:41 UTC
Update Date2020-05-21 16:28:00 UTC
BMDB IDBMDB0007405
Secondary Accession Numbers
  • BMDB07405
Metabolite Identification
Common NameDG(20:1(11Z)/22:0/0:0)
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
Synonyms
ValueSource
1-Eicosenoyl-2-behenoyl-sn-glycerolHMDB
DAG(20:1/22:0)HMDB
DAG(20:1N9/22:0)HMDB
DAG(20:1W9/22:0)HMDB
DAG(42:1)HMDB
DG(20:1/22:0)HMDB
DG(20:1N9/22:0)HMDB
DG(20:1W9/22:0)HMDB
DG(42:1)HMDB
DiacylglycerolHMDB
Diacylglycerol(20:1/22:0)HMDB
Diacylglycerol(20:1n9/22:0)HMDB
Diacylglycerol(20:1W9/22:0)HMDB
Diacylglycerol(42:1)HMDB
DiglycerideHMDB
1-(11-Eicosenoyl)-2-docosanoyl-sn-glycerolHMDB
DG(20:1(11Z)/22:0/0:0)Lipid Annotator
Chemical FormulaC45H86O5
Average Molecular Weight707.1613
Monoisotopic Molecular Weight706.647525862
IUPAC Name(2S)-1-hydroxy-3-[(11Z)-icos-11-enoyloxy]propan-2-yl docosanoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H]\C(CCCCCCCC)=C(/[H])CCCCCCCCCC(=O)OC[C@]([H])(CO)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-/m0/s1
InChI KeyKKUJWTOLSKTBLP-QGWKGAMHSA-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
logP10.77ALOGPS
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
Polarizability94.19 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, Positivesplash10-00di-0000000900-015317c8359692a7e8a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014t-0009003100-400256e1a14e877c54ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bb-0009000300-e9153d81a31aa4a6ea1aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052r-2009100300-d456b4568e686cc6e0a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-2009000000-a0aa52ba96556ece4129View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-2149000000-3ceaacc7a6502cd56ba4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000000900-bbabbadc5a75f85bb41eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014t-0009003100-f7f82fdaeb34b19af78eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bb-0009000300-d75836898d4047bcfaa9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000900-77b49398252260036544View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000000900-77b49398252260036544View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0150-0009600100-502355532c27af995ec0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05tk-0109001200-2a1cd1db5db0c14fedd6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dj-1139000000-7e482536f1e41acc15b2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dm-7944000000-d5dcf9e961b143096246View 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 IDHMDB0007405
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024598
KNApSAcK IDNot Available
Chemspider ID7822825
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543875
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(20:1(11Z)/22:0/0:0) → Cytidine monophosphate + PE(20:1(11Z)/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(20:1(11Z)/22:0/0:0) + Docosanoyl-CoA → TG(20:1(11Z)/22:0/22:0) + Coenzyme Adetails
DG(20:1(11Z)/22:0/0:0) + Erucoyl-CoA → TG(20:1(11Z)/22:0/22:1(13Z)) + Coenzyme Adetails
DG(20:1(11Z)/22:0/0:0) + Clupanodonyl CoA → TG(20:1(11Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails