Showing metabocard for DG(20:0/22:2(13Z,16Z)/0:0) (BMDB0007378)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:36:09 UTC
Update Date2020-05-21 16:27:59 UTC
BMDB IDBMDB0007378
Secondary Accession Numbers
  • BMDB07378
Metabolite Identification
Common NameDG(20:0/22:2(13Z,16Z)/0:0)
DescriptionDG(20:0/22:2(13Z,16Z)/0:0)[iso2], also known as dg(20:0/22:2(13z,16z)/0:0)[iso2] or DAG(20:0/22:2), belongs to the class of organic compounds known as 1,2-dg(20:0/22:2(13z,16z)/0:0)[iso2]s. These are dg(20:0/22:2(13z,16z)/0:0)[iso2]s containing a glycerol acylated at positions 1 and 2. Thus, DG(20:0/22:2(13Z,16Z)/0:0)[iso2] is considered to be a diradylglycerol lipid molecule. DG(20:0/22:2(13Z,16Z)/0:0)[iso2] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, DG(20:0/22:2(13Z,16Z)/0:0)[iso2] is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(20:0/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Arachidonyl-2-docosadienoyl-sn-glycerolHMDB
DAG(20:0/22:2)HMDB
DAG(20:0/22:2N6)HMDB
DAG(20:0/22:2W6)HMDB
DAG(42:2)HMDB
DG(20:0/22:2)HMDB
DG(20:0/22:2N6)HMDB
DG(20:0/22:2W6)HMDB
DG(42:2)HMDB
DiacylglycerolHMDB
Diacylglycerol(20:0/22:2)HMDB
Diacylglycerol(20:0/22:2n6)HMDB
Diacylglycerol(20:0/22:2W6)HMDB
Diacylglycerol(42:2)HMDB
DiglycerideHMDB
1-Eicosanoyl-2-(13Z,16Z-docosadienoyl)-sn-glycerolHMDB
DG(20:0/22:2(13Z,16Z)/0:0)Lipid Annotator
Chemical FormulaC45H84O5
Average Molecular Weight705.1455
Monoisotopic Molecular Weight704.631875798
IUPAC Name(2S)-1-hydroxy-3-(icosanoyloxy)propan-2-yl (13Z,16Z)-docosa-13,16-dienoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCC\C=C/C\C=C/CCCCC
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/h11,13,17,19,43,46H,3-10,12,14-16,18,20-42H2,1-2H3/b13-11-,19-17-/t43-/m0/s1
InChI KeyPYAZOTPSRUDMOJ-SLORSEGHSA-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
logP10.76ALOGPS
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
Polarizability93.87 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-f57912e5a3115d4646feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014x-0009003100-365b449e983160c4af38View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bf-0009000300-737ba75e32beaae6116bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000000900-46bb7b8edeb864cb1e02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014x-0009003100-ec405fe02b8fde81baf6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bf-0009000300-5fe494f5e1a8dd6ee96dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066r-1019001300-d788248072a1433c0739View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1139000000-c68e25817d8f1578a979View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-4239000000-44a7dbe0dedca793c27aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000900-22a8e38c4a96cde10ac8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000000900-22a8e38c4a96cde10ac8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014o-0009600100-8ff0f2855d99fd52180aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udr-2009000500-92c7b415e78f57687dbfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-2019000000-bb0a723773352d096d3fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08g3-2039000000-e7f7d04afc71c45d286bView 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 IDHMDB0007378
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024571
KNApSAcK IDNot Available
Chemspider ID7822846
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543896
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(20:0/22:2(13Z,16Z)/0:0) → Cytidine monophosphate + PE(20:0/22:2(13Z,16Z))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(20:0/22:2(13Z,16Z)/0:0) + Clupanodonyl CoA → TG(20:0/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails
DG(20:0/22:2(13Z,16Z)/0:0) + Tetracosanoyl-CoA → TG(20:0/22:2(13Z,16Z)/24:0) + Coenzyme Adetails