Showing metabocard for DG(18:3(6Z,9Z,12Z)/22:0/0:0) (BMDB0007289)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:34:22 UTC
Update Date2020-05-21 16:27:55 UTC
BMDB IDBMDB0007289
Secondary Accession Numbers
  • BMDB07289
Metabolite Identification
Common NameDG(18:3(6Z,9Z,12Z)/22:0/0:0)
DescriptionDG(18:3(6Z,9Z,12Z)/22:0/0:0)[iso2], also known as dg(18:3(6z,9z,12z)/22:0/0:0)[iso2] or DAG(18:3/22:0), belongs to the class of organic compounds known as 1,2-dg(18:3(6z,9z,12z)/22:0/0:0)[iso2]s. These are dg(18:3(6z,9z,12z)/22:0/0:0)[iso2]s containing a glycerol acylated at positions 1 and 2. Thus, DG(18:3(6Z,9Z,12Z)/22:0/0:0)[iso2] is considered to be a diradylglycerol lipid molecule. DG(18:3(6Z,9Z,12Z)/22:0/0:0)[iso2] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, DG(18:3(6Z,9Z,12Z)/22:0/0:0)[iso2] is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/22:4(7Z,10Z,13Z,16Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-g-Linolenoyl-2-behenoyl-sn-glycerolHMDB
1-gamma-Linolenoyl-2-behenoyl-sn-glycerolHMDB
DAG(18:3/22:0)HMDB
DAG(18:3N6/22:0)HMDB
DAG(18:3W6/22:0)HMDB
DAG(40:3)HMDB
DG(18:3/22:0)HMDB
DG(18:3N6/22:0)HMDB
DG(18:3W6/22:0)HMDB
DG(40:3)HMDB
DiacylglycerolHMDB
Diacylglycerol(18:3/22:0)HMDB
Diacylglycerol(18:3n6/22:0)HMDB
Diacylglycerol(18:3W6/22:0)HMDB
Diacylglycerol(40:3)HMDB
DiglycerideHMDB
1-(6Z,9Z,12Z-Octadecatrienoyl)-2-docosanoyl-sn-glycerolHMDB
DG(18:3(6Z,9Z,12Z)/22:0/0:0)Lipid Annotator
Chemical FormulaC43H78O5
Average Molecular Weight675.0764
Monoisotopic Molecular Weight674.584925606
IUPAC Name(2S)-1-hydroxy-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propan-2-yl docosanoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CCCCCCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C43H78O5/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-43(46)48-41(39-44)40-47-42(45)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h12,14,18,23,27,29,41,44H,3-11,13,15-17,19-22,24-26,28,30-40H2,1-2H3/b14-12-,23-18-,29-27-/t41-/m0/s1
InChI KeyWHZBAPHGAMGIDL-JWYCNVSLSA-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
logP10.58ALOGPS
logP14.47ChemAxon
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 Count39ChemAxon
Refractivity207.86 m³·mol⁻¹ChemAxon
Polarizability88.01 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, Positivesplash10-0006-0000009000-c3dce39756875b552b1eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052t-0009004000-0dc6f63318461e55dabdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000n-0009004000-ef08cead21e24fb01e82View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000009000-577a9b380da668614490View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000009000-577a9b380da668614490View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0b90-0009601000-a4a7b8f5295ff27846b2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-2047009000-ae2e79a7849c0d1a072bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00g0-4049001000-362576ae5bc65327c218View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3194000000-a562422d6ce0ac2b89daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00fr-3109015000-f053352e7c145eb0d559View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-4129011000-7c0b37f3f79c0604dc38View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ea-9837000000-4c620e9e07395ec48299View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000009000-e31af479d30e7d5a40b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052t-0009004000-06d2cbbeebb2dd1e9655View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000n-0009004000-0fd6dd0d971a80bf5626View 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 IDHMDB0007289
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024482
KNApSAcK IDNot Available
Chemspider ID24766039
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53478131
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(18:3(6Z,9Z,12Z)/22:0/0:0) → Cytidine monophosphate + PE(18:3(6Z,9Z,12Z)/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(18:3(6Z,9Z,12Z)/22:0/0:0) + Docosanoyl-CoA → TG(18:3(6Z,9Z,12Z)/22:0/22:0) + Coenzyme Adetails
DG(18:3(6Z,9Z,12Z)/22:0/0:0) + Erucoyl-CoA → TG(18:3(6Z,9Z,12Z)/22:0/22:1(13Z)) + Coenzyme Adetails
DG(18:3(6Z,9Z,12Z)/22:0/0:0) + Clupanodonyl CoA → TG(18:3(6Z,9Z,12Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails