Showing metabocard for DG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/0:0) (BMDB0007461)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:37:48 UTC
Update Date2020-05-21 16:28:02 UTC
BMDB IDBMDB0007461
Secondary Accession Numbers
  • BMDB07461
Metabolite Identification
Common NameDG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/0:0)
DescriptionDG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/0:0), also known as dg(20:3(5z,8z,11z)/20:4(8z,11z,14z,17z)/0:0) or DG(20:3/20:4), belongs to the class of organic compounds known as 1,2-dg(20:3(5z,8z,11z)/20:4(8z,11z,14z,17z)/0:0)s. These are dg(20:3(5z,8z,11z)/20:4(8z,11z,14z,17z)/0:0)s containing a glycerol acylated at positions 1 and 2. DG(20:3(5Z,8Z,11Z)/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(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/0:0) can be biosynthesized from PA(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)); which is catalyzed by the enzyme phosphatidate phosphatase. Furthermore, DG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/0:0) and eicosapentaenoyl-CoA can be converted into TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)); which is catalyzed by the enzyme dg(20:3(5z,8z,11z)/20:4(8z,11z,14z,17z)/0:0) O-acyltransferase. Furthermore, DG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/0:0) can be biosynthesized from PA(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)); which is catalyzed by the enzyme phosphatidate phosphatase. Finally, DG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/0:0) and docosahexaenoyl-CoA can be converted into TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) through the action of the enzyme dg(20:3(5z,8z,11z)/20:4(8z,11z,14z,17z)/0:0) O-acyltransferase. In cattle, DG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/0:0) is involved in a couple of metabolic pathways, which include de novo triacylglycerol biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) pathway and de novo triacylglycerol biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Diacylglycerol(20:3/20:4)HMDB
DG(20:3/20:4)HMDB
DAG(40:7)HMDB
DiglycerideHMDB
DG(40:7)HMDB
DiacylglycerolHMDB
DAG(20:3/20:4)HMDB
1-Meadoyl-2-eicsoatetraenoyl-sn-glycerolHMDB
1-(5Z,8Z,11Z-Eicosatrienoyl)-2-(8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycerolHMDB
Diacylglycerol(40:7)HMDB
DG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/0:0)Lipid Annotator
Chemical FormulaC43H70O5
Average Molecular Weight667.0129
Monoisotopic Molecular Weight666.52232535
IUPAC Name(2S)-1-hydroxy-3-[(5Z,8Z,11Z)-icosa-5,8,11-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)CCC\C=C/C\C=C/C\C=C/CCCCCCCC)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C43H70O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-42(45)47-40-41(39-44)48-43(46)38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h6,8,12,14,17-20,23-26,29,31,41,44H,3-5,7,9-11,13,15-16,21-22,27-28,30,32-40H2,1-2H3/b8-6-,14-12-,19-17-,20-18-,25-23-,26-24-,31-29-/t41-/m0/s1
InChI KeyCWKVHVZKEKWSIB-FYJQDSGBSA-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
logP9.12ALOGPS
logP13.03ChemAxon
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 Count35ChemAxon
Refractivity212.32 m³·mol⁻¹ChemAxon
Polarizability82.79 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 (Non-derivatized) - 70eV, Positivesplash10-03di-5498112000-cf5c089c1280430ab1aaView in MoNA
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, Positivesplash10-03y1-1049005000-ab56e223fc020b50a8b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ds-3198112000-e86f59f686bbd252c7cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03ds-2096231000-aab3d5eda8c46f23f5c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ap0-0039003000-36d1b8aa34aa1f8eed44View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1049001000-cccd03748b755d0dd80aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3059000000-512bc21c9ffcb83daf00View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000009000-64b93739ea49f5c060aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0009004000-b68e929b078fe269c1ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0009004000-6187f5d5988d4bdb984aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-1145059000-f836c56239ed5623988bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1096031000-f2a4ad90e5216e73df7bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0596030000-0f13bb38cf159cf5b099View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000009000-280b86e4414b53facf72View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000009000-280b86e4414b53facf72View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0019-0009000000-e78571d238632ed10ea0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0017009000-84cfc2257ba85c8193efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-4029000000-2511df6d0bdb7094ac35View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-4039000000-967708751ed79c459b56View 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 IDHMDB0007461
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 Compound53478256
PDB IDNot Available
ChEBI ID89787
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(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/0:0) → Cytidine monophosphate + PE(20:3(5Z,8Z,11Z)/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(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/0:0) + Erucoyl-CoA → TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z)) + Coenzyme Adetails
DG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/0:0) + Clupanodonyl CoA → TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails