Showing metabocard for DG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) (BMDB0007554)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:39:41 UTC
Update Date2020-05-21 16:28:04 UTC
BMDB IDBMDB0007554
Secondary Accession Numbers
  • BMDB07554
Metabolite Identification
Common NameDG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0)
DescriptionDG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0), also known as DAG(20:4/22:5) or dg(20:4(8z,11z,14z,17z)/22:5(4z,7z,10z,13z,16z)/0:0), belongs to the class of organic compounds known as 1,2-dg(20:4(8z,11z,14z,17z)/22:5(4z,7z,10z,13z,16z)/0:0)s. These are dg(20:4(8z,11z,14z,17z)/22:5(4z,7z,10z,13z,16z)/0:0)s containing a glycerol acylated at positions 1 and 2. DG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/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(4Z,7Z,10Z,13Z,16Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) can be biosynthesized from PA(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)) through the action of the enzyme phosphatidate phosphatase. Furthermore, DG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) and tetracosanoyl-CoA can be converted into TG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0) through the action of the enzyme dg(20:4(8z,11z,14z,17z)/22:5(4z,7z,10z,13z,16z)/0:0) O-acyltransferase. Furthermore, DG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) can be biosynthesized from PA(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)) through the action of the enzyme phosphatidate phosphatase. Furthermore, DG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) and clupanodonoyl-CoA can be converted into TG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) through the action of the enzyme dg(20:4(8z,11z,14z,17z)/22:5(4z,7z,10z,13z,16z)/0:0) O-acyltransferase. Finally, CDP-Ethanolamine and DG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) can be converted into cytidine monophosphate and PE(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)) through the action of the enzyme choline/ethanolaminephosphotransferase. In cattle, DG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) is involved in a few metabolic pathways, which include de novo triacylglycerol biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0) pathway, de novo triacylglycerol biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) pathway, and phosphatidylethanolamine biosynthesis pe(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DAG(20:4/22:5)HMDB
Diacylglycerol(42:9)HMDB
Diacylglycerol(20:4/22:5)HMDB
DiglycerideHMDB
DAG(42:9)HMDB
DiacylglycerolHMDB
1-Eicsoatetraenoyl-2-osbondoyl-sn-glycerolHMDB
DG(42:9)HMDB
1-(8Z,11Z,14Z,17Z-Eicosapentaenoyl)-2-(4Z,7Z,10Z,13Z,16Z-docosapentaenoyl)-sn-glycerolHMDB
DG(20:4/22:5)HMDB
DG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/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 (4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-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)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC
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/h6,8,11-14,17-20,22,24-25,27-28,30,34,36,43,46H,3-5,7,9-10,15-16,21,23,26,29,31-33,35,37-42H2,1-2H3/b8-6-,13-11-,14-12-,19-17-,20-18-,24-22-,27-25-,30-28-,36-34-/t43-/m0/s1
InChI KeyPGJUXLOMVCPELB-QVWQVYLSSA-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
logP8.68ALOGPS
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
Polarizability84.41 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-d32e8e508e42076be2beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zi9-5139000000-14fceb0844d29f493186View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-2015039000-0a024d26c26a349593cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dr-1139001000-84cfe59667a3cb8ca06aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03ei-0279000000-bb9d5c7cc3e8ad1a5883View 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, Positivesplash10-0a4i-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 IDHMDB0007554
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 Compound53478332
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(4Z,7Z,10Z,13Z,16Z)/0:0) → Cytidine monophosphate + PE(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))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(4Z,7Z,10Z,13Z,16Z)/0:0) + Clupanodonyl CoA → TG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails