Showing metabocard for DG(18:3(6Z,9Z,12Z)/20:0/0:0) (BMDB0007281)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:34:12 UTC
Update Date2020-05-21 16:27:54 UTC
BMDB IDBMDB0007281
Secondary Accession Numbers
  • BMDB07281
Metabolite Identification
Common NameDG(18:3(6Z,9Z,12Z)/20:0/0:0)
DescriptionDG(18:3(6Z,9Z,12Z)/20:0/0:0)[iso2], also known as DAG(18:3/20:0) or dg(18:3(6z,9z,12z)/20:0/0:0)[iso2], belongs to the class of organic compounds known as 1,2-dg(18:3(6z,9z,12z)/20:0/0:0)[iso2]s. These are dg(18:3(6z,9z,12z)/20:0/0:0)[iso2]s containing a glycerol acylated at positions 1 and 2. Thus, DG(18:3(6Z,9Z,12Z)/20:0/0:0)[iso2] is considered to be a diradylglycerol lipid molecule. DG(18:3(6Z,9Z,12Z)/20:0/0:0)[iso2] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, DG(18:3(6Z,9Z,12Z)/20:0/0:0)[iso2] is involved in a few metabolic pathways, which include de novo triacylglycerol biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/20:3(5Z,8Z,11Z)) pathway, de novo triacylglycerol biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/22:2(13Z,16Z)) pathway, and de novo triacylglycerol biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/24:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DG(38:3)HMDB
1-g-Linolenoyl-2-arachidonyl-sn-glycerolHMDB
DAG(18:3/20:0)HMDB
Diacylglycerol(38:3)HMDB
DiglycerideHMDB
Diacylglycerol(18:3/20:0)HMDB
DG(18:3/20:0)HMDB
DiacylglycerolHMDB
1-(6Z,9Z,12Z-Octadecatrienoyl)-2-eicosanoyl-sn-glycerolHMDB
DAG(38:3)HMDB
DG(18:3(6Z,9Z,12Z)/20:0/0:0)Lipid Annotator
Chemical FormulaC41H74O5
Average Molecular Weight647.0233
Monoisotopic Molecular Weight646.553625478
IUPAC Name(2S)-1-hydroxy-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propan-2-yl icosanoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CCCCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C41H74O5/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-41(44)46-39(37-42)38-45-40(43)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h12,14,18,21,25,27,39,42H,3-11,13,15-17,19-20,22-24,26,28-38H2,1-2H3/b14-12-,21-18-,27-25-/t39-/m0/s1
InChI KeyAHFXSFABMNMUBM-WIYORBNSSA-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
logP10.39ALOGPS
logP13.58ChemAxon
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 Count37ChemAxon
Refractivity198.65 m³·mol⁻¹ChemAxon
Polarizability83.7 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 GC-MSPredicted GC-MS Spectrum - GC-MS ("DG(18:3(6Z,9Z,12Z)/20:0/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000009000-2259905083239ea1ecd7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0179-0009004000-14cd690d005919543c39View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02tr-0009004000-56cbbdc7194190cd02baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-2047009000-6cd3c819839c0350a1dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-020c-4069001000-4a72ad7f614a3f653136View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-2093000000-6af4fe4c16c757708b3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000009000-63265ec42c7a24551d59View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0179-0009004000-f7b13d3ba6b725631963View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02tr-0009004000-9b0bff1bd6a043e7ebd8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-3195026000-a17086be3ad1dd4db100View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-4193011000-c92ae65b86b74d6fc818View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9652000000-ab785dcf3f0dcf5e41a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000009000-d37410aaac9880d0864dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000009000-d37410aaac9880d0864dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4o-0009000000-136129b666cf37486f7bView 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 IDHMDB0007281
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024474
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53478123
PDB IDNot Available
ChEBI ID89159
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(18:3(6Z,9Z,12Z)/20:0/0:0) → Cytidine monophosphate + PE(18:3(6Z,9Z,12Z)/20:0)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(18:3(6Z,9Z,12Z)/20:0/0:0) + Eicosanoyl-CoA → TG(18:3(6Z,9Z,12Z)/20:0/20:0) + Coenzyme Adetails
DG(18:3(6Z,9Z,12Z)/20:0/0:0) + Gondoyl-CoA → TG(18:3(6Z,9Z,12Z)/20:0/20:1(11Z)) + Coenzyme Adetails
DG(18:3(6Z,9Z,12Z)/20:0/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(18:3(6Z,9Z,12Z)/20:0/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(18:3(6Z,9Z,12Z)/20:0/0:0) + Docosanoyl-CoA → TG(18:3(6Z,9Z,12Z)/20:0/22:0) + Coenzyme Adetails
DG(18:3(6Z,9Z,12Z)/20:0/0:0) + Erucoyl-CoA → TG(18:3(6Z,9Z,12Z)/20:0/22:1(13Z)) + Coenzyme Adetails
DG(18:3(6Z,9Z,12Z)/20:0/0:0) + Clupanodonyl CoA → TG(18:3(6Z,9Z,12Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails