Showing metabocard for DG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/0:0) (BMDB0007555)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:39:42 UTC
Update Date2020-05-21 16:28:05 UTC
BMDB IDBMDB0007555
Secondary Accession Numbers
  • BMDB07555
Metabolite Identification
Common NameDG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/0:0)
DescriptionDG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/0:0), also known as DG(20:4/22:5) or dg(20:4(8z,11z,14z,17z)/22:5(7z,10z,13z,16z,19z)/0:0), belongs to the class of organic compounds known as 1,2-dg(20:4(8z,11z,14z,17z)/22:5(7z,10z,13z,16z,19z)/0:0)s. These are dg(20:4(8z,11z,14z,17z)/22:5(7z,10z,13z,16z,19z)/0:0)s containing a glycerol acylated at positions 1 and 2. DG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/0:0) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). DG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/0:0) can be biosynthesized from PA(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)) through its interaction with the enzyme phosphatidate phosphatase. Furthermore, DG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/0:0) and docosahexaenoyl-CoA can be converted into TG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) through the action of the enzyme dg(20:4(8z,11z,14z,17z)/22:5(7z,10z,13z,16z,19z)/0:0) O-acyltransferase. Furthermore, DG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/0:0) can be biosynthesized from PA(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)); which is catalyzed by the enzyme phosphatidate phosphatase. Furthermore, DG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/0:0) and nervonoyl-CoA can be converted into TG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z)); which is mediated by the enzyme dg(20:4(8z,11z,14z,17z)/22:5(7z,10z,13z,16z,19z)/0:0) O-acyltransferase. Furthermore, DG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/0:0) can be biosynthesized from PA(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)) through the action of the enzyme phosphatidate phosphatase. Finally, DG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/0:0) and clupanodonoyl-CoA can be converted into TG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) through the action of the enzyme dg(20:4(8z,11z,14z,17z)/22:5(7z,10z,13z,16z,19z)/0:0) O-acyltransferase. In cattle, DG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/0:0) is involved in a few metabolic pathways, which include de novo triacylglycerol biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) pathway, de novo triacylglycerol biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z)) pathway, and de novo triacylglycerol biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DG(20:4/22:5)HMDB
DAG(20:4/22:5)HMDB
Diacylglycerol(42:9)HMDB
Diacylglycerol(20:4/22:5)HMDB
DiglycerideHMDB
DAG(42:9)HMDB
DiacylglycerolHMDB
DG(42:9)HMDB
1-(8Z,11Z,14Z,17Z-Eicosapentaenoyl)-2-(7Z,10Z,13Z,16Z,19Z-docosapentaenoyl)-sn-glycerolHMDB
1-Eicsoatetraenoyl-2-docosapentaenoyl-sn-glycerolHMDB
DG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/0:0)Lipid Annotator
Chemical FormulaC45H70O5
Average Molecular Weight691.0343
Monoisotopic Molecular Weight690.52232535
IUPAC Name(2S)-1-hydroxy-3-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]propan-2-yl (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C45H70O5/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/h5-8,11-14,17-20,22,24-25,27-28,30,43,46H,3-4,9-10,15-16,21,23,26,29,31-42H2,1-2H3/b7-5-,8-6-,13-11-,14-12-,19-17-,20-18-,24-22-,27-25-,30-28-/t43-/m0/s1
InChI KeyFQRITGZWODRJRD-FAFYFKLOSA-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
logP8.61ALOGPS
logP13.19ChemAxon
logS-7.6ALOGPS
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
Refractivity223.76 m³·mol⁻¹ChemAxon
Polarizability83.89 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, Positivesplash10-0a4i-0000000900-add90c975ba308f59ee0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03kr-0009003000-c3ba7efabbb01433d354View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08g9-0009001300-d1657d80f0d893091f85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0019007000-500ae82696cda41ce6f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uki-4019000000-5916b3dda466228ebf7bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zi9-5139000000-4115ca182c37b57ecfebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000900-813db042689ca343bc09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000900-813db042689ca343bc09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a60-0009600100-de7d132de3677b45f9c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1014039000-8e4dab1f58a951d273ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dr-2049002000-1f2876331af49c23ef92View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03ei-0289000000-0c00de65f2b6a0deeb4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000900-0160669cdc989893514bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03kr-0009003000-1928b32572930e5b8614View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08g9-0009001300-96b6ed238465af1a2b00View 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 IDHMDB0007555
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 Compound53478333
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(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/0:0) → Cytidine monophosphate + PE(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))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(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/0:0) + Clupanodonyl CoA → TG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails