Showing metabocard for DG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/0:0) (BMDB0007316)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:34:54 UTC
Update Date2020-05-21 16:27:56 UTC
BMDB IDBMDB0007316
Secondary Accession Numbers
  • BMDB07316
Metabolite Identification
Common NameDG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/0:0)
DescriptionDG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/0:0), also known as DG(18:3/20:4) or dg(18:3(9z,12z,15z)/20:4(8z,11z,14z,17z)/0:0), belongs to the class of organic compounds known as 1,2-dg(18:3(9z,12z,15z)/20:4(8z,11z,14z,17z)/0:0)s. These are dg(18:3(9z,12z,15z)/20:4(8z,11z,14z,17z)/0:0)s containing a glycerol acylated at positions 1 and 2. DG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/0:0) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). DG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/0:0) can be biosynthesized from PA(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)) through its interaction with the enzyme phosphatidate phosphatase. Furthermore, DG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/0:0) and eicosatetraenoyl-CoA can be converted into TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)) through the action of the enzyme dg(18:3(9z,12z,15z)/20:4(8z,11z,14z,17z)/0:0) O-acyltransferase. Furthermore, DG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/0:0) can be biosynthesized from PA(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)) through the action of the enzyme phosphatidate phosphatase. Finally, DG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/0:0) and adrenoyl-CoA can be converted into TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)); which is catalyzed by the enzyme dg(18:3(9z,12z,15z)/20:4(8z,11z,14z,17z)/0:0) O-acyltransferase. In cattle, DG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/0:0) is involved in a couple of metabolic pathways, which include de novo triacylglycerol biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)) pathway and de novo triacylglycerol biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DG(18:3/20:4)HMDB
DG(38:7)HMDB
DAG(38:7)HMDB
Diacylglycerol(38:7)HMDB
1-a-Linolenoyl-2-eicsoatetraenoyl-sn-glycerolHMDB
DAG(18:3/20:4)HMDB
DiacylglycerolHMDB
Diacylglycerol(18:3/20:4)HMDB
1-(9Z,12Z,15Z-Octadeatrienoyl)-2-(8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycerolHMDB
DiglycerideHMDB
DG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/0:0)Lipid Annotator
Chemical FormulaC41H66O5
Average Molecular Weight638.9597
Monoisotopic Molecular Weight638.491025222
IUPAC Name(2S)-1-hydroxy-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propan-2-yl (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C41H66O5/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/h5-8,11-14,17-19,21-22,24,39,42H,3-4,9-10,15-16,20,23,25-38H2,1-2H3/b7-5-,8-6-,13-11-,14-12-,19-17-,21-18-,24-22-/t39-/m0/s1
InChI KeyKRRJLZAVCIHCJZ-BIWBDPSSSA-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
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
logP8.58ALOGPS
logP12.14ChemAxon
logS-7.5ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count33ChemAxon
Refractivity203.12 m³·mol⁻¹ChemAxon
Polarizability78.07 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(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1045009000-ffac10838dbbb2ddcdcbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05di-6095000000-d943d8b4393913ab2709View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kdi-6194000000-96d60c03dc97f5aa2710View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000009000-e35648bd7441f03ca43dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01w0-0009004000-981b6c509ea3d621d729View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06ri-0009004000-6e105c290024d08a4c4fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000009000-a3bdf4283133ae4a6142View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000009000-a3bdf4283133ae4a6142View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a60-0009000000-44411647114c10c727d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1142094000-b62858128cacd03aa422View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-3195030000-ae3048d56154f930c6f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06ri-1797010000-5882ba1cefa96cfebedbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000009000-38ae02c951d911581b96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01w0-0009004000-e09ce3df97bbbf499862View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06ri-0009004000-d01b00aa0d895836b31aView 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 IDHMDB0007316
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 Compound53478152
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(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/0:0) → Cytidine monophosphate + PE(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))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(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/0:0) + Clupanodonyl CoA → TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails