Showing metabocard for DG(20:0/20:4(5Z,8Z,11Z,14Z)/0:0) (BMDB0007373)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:36:03 UTC
Update Date2020-05-21 16:27:58 UTC
BMDB IDBMDB0007373
Secondary Accession Numbers
  • BMDB07373
Metabolite Identification
Common NameDG(20:0/20:4(5Z,8Z,11Z,14Z)/0:0)
DescriptionDG(20:0/20:4(5Z,8Z,11Z,14Z)/0:0)[iso2], also known as dg(20:0/20:4(5z,8z,11z,14z)/0:0)[iso2] or DAG(20:0/20:4), belongs to the class of organic compounds known as 1,2-dg(20:0/20:4(5z,8z,11z,14z)/0:0)[iso2]s. These are dg(20:0/20:4(5z,8z,11z,14z)/0:0)[iso2]s containing a glycerol acylated at positions 1 and 2. Thus, DG(20:0/20:4(5Z,8Z,11Z,14Z)/0:0)[iso2] is considered to be a diradylglycerol lipid molecule. DG(20:0/20:4(5Z,8Z,11Z,14Z)/0:0)[iso2] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, DG(20:0/20:4(5Z,8Z,11Z,14Z)/0:0)[iso2] is involved in the metabolic pathway called phosphatidylcholine biosynthesis PC(20:0/20:4(5Z,8Z,11Z,14Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2-DG 20:0/20:4(omega-6)ChEBI
1-Arachidoyl-2-arachidonoyl-sn-glycerolChEBI
1-Eicosanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycerolChEBI
1-Eicosanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerolChEBI
1-Icosanoyl-2-(5Z,8Z,11Z,14Z)-icosatetraenoyl-sn-glycerolChEBI
DAG(20:0/20:4)ChEBI
DAG(20:0/20:4N6)ChEBI
DAG(20:0/20:4OMEGA6)ChEBI
DAG(40:4)ChEBI
DG(20:0/20:4)ChEBI
DG(20:0/20:4/0:0)ChEBI
DG(20:0/20:4N6)ChEBI
DG(20:0/20:4OMEGA6)ChEBI
DG(40:4)ChEBI
Diacylglycerol(20:0/20:4)ChEBI
Diacylglycerol(20:0/20:4n6)ChEBI
Diacylglycerol(20:0/20:4omega6)ChEBI
Diacylglycerol(40:4)ChEBI
1-Arachidonyl-2-arachidonoyl-sn-glycerolHMDB
DiglycerideHMDB
DiacylglycerolHMDB
DG(20:0/20:4(5Z,8Z,11Z,14Z)/0:0)Lipid Annotator, ChEBI
Chemical FormulaC43H76O5
Average Molecular Weight673.0605
Monoisotopic Molecular Weight672.569275542
IUPAC Name(2S)-1-hydroxy-3-(icosanoyloxy)propan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCCCCCCCCCCCCCC)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C43H76O5/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/h12,14,18,20,24,26,30,32,41,44H,3-11,13,15-17,19,21-23,25,27-29,31,33-40H2,1-2H3/b14-12-,20-18-,26-24-,32-30-/t41-/m0/s1
InChI KeyOUGXERRDRINUQU-AICYSBPGSA-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
logP10.45ALOGPS
logP14.11ChemAxon
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 Count38ChemAxon
Refractivity208.97 m³·mol⁻¹ChemAxon
Polarizability86.91 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, Positivesplash10-014i-3094112000-0708639594e111a0ba2bView 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, Positivesplash10-07p1-1089005000-3df06ce992f1ab964f87View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014s-2094001000-41fd7576ec94655e18f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gba-1093021000-f165689d9470f09d4832View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03kc-0049003000-dac3a755b1ac54605a00View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-1059000000-597d3dd5488412b8e02aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dl-4059000000-621f7665e06a1f63733cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000009000-7879d85c13086e66b079View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-09k9-0009004000-c2fcf1124137c932a0c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-04i3-0009004000-f29f052049acd35f1947View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000009000-d45cdcefb72f30be67fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000009000-d45cdcefb72f30be67fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001o-0009000000-e6c563422fc7320e75bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1007009000-9f9229adab9de18177ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-2029001000-d6de75c3423703ff9932View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0r03-2049000000-84c85cea711b407eaaa4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01w0-2097027000-593e4b0bb0a9f73fcbd4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01pa-2195001000-707b41356060099a2600View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06ri-3269000000-b7ed1c106a322b9a1904View 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 IDHMDB0007373
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 Compound9543830
PDB IDNot Available
ChEBI ID77093
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(20:0/20:4(5Z,8Z,11Z,14Z)/0:0) → Cytidine monophosphate + PE(20:0/20:4(5Z,8Z,11Z,14Z))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(20:0/20:4(5Z,8Z,11Z,14Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(20:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(20:0/20:4(5Z,8Z,11Z,14Z)/0:0) + Docosanoyl-CoA → TG(20:0/20:4(5Z,8Z,11Z,14Z)/22:0) + Coenzyme Adetails
DG(20:0/20:4(5Z,8Z,11Z,14Z)/0:0) + Erucoyl-CoA → TG(20:0/20:4(5Z,8Z,11Z,14Z)/22:1(13Z)) + Coenzyme Adetails
DG(20:0/20:4(5Z,8Z,11Z,14Z)/0:0) + Clupanodonyl CoA → TG(20:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails
DG(20:0/20:4(5Z,8Z,11Z,14Z)/0:0) + Tetracosanoyl-CoA → TG(20:0/20:4(5Z,8Z,11Z,14Z)/24:0) + Coenzyme Adetails