Showing metabocard for DG(20:1(11Z)/20:3(5Z,8Z,11Z)/0:0) (BMDB0007400)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:36:35 UTC
Update Date2020-05-21 16:27:59 UTC
BMDB IDBMDB0007400
Secondary Accession Numbers
  • BMDB07400
Metabolite Identification
Common NameDG(20:1(11Z)/20:3(5Z,8Z,11Z)/0:0)
DescriptionDG(20:1(11Z)/20:3(5Z,8Z,11Z)/0:0), also known as dg(20:1(11z)/20:3(5z,8z,11z)/0:0) or DAG(20:1/20:3), belongs to the class of organic compounds known as 1,2-dg(20:1(11z)/20:3(5z,8z,11z)/0:0)s. These are dg(20:1(11z)/20:3(5z,8z,11z)/0:0)s containing a glycerol acylated at positions 1 and 2. DG(20:1(11Z)/20:3(5Z,8Z,11Z)/0:0) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). DG(20:1(11Z)/20:3(5Z,8Z,11Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(20:1(11Z)/20:3(5Z,8Z,11Z)/0:0) can be biosynthesized from PA(20:1(11Z)/20:3(5Z,8Z,11Z)); which is catalyzed by the enzyme phosphatidate phosphatase. Furthermore, DG(20:1(11Z)/20:3(5Z,8Z,11Z)/0:0) and meadoyl-CoA can be converted into TG(20:1(11Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)) through the action of the enzyme dg(20:1(11z)/20:3(5z,8z,11z)/0:0) O-acyltransferase. Furthermore, DG(20:1(11Z)/20:3(5Z,8Z,11Z)/0:0) can be biosynthesized from PA(20:1(11Z)/20:3(5Z,8Z,11Z)) through the action of the enzyme phosphatidate phosphatase. Finally, DG(20:1(11Z)/20:3(5Z,8Z,11Z)/0:0) and docosanoyl-CoA can be converted into TG(20:1(11Z)/20:3(5Z,8Z,11Z)/22:0) through its interaction with the enzyme dg(20:1(11z)/20:3(5z,8z,11z)/0:0) O-acyltransferase. In cattle, DG(20:1(11Z)/20:3(5Z,8Z,11Z)/0:0) is involved in a couple of metabolic pathways, which include de novo triacylglycerol biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)) pathway and de novo triacylglycerol biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/22:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Eicosenoyl-2-meadoyl-sn-glycerolHMDB
DAG(20:1/20:3)HMDB
DAG(20:1N9/20:3N9)HMDB
DAG(20:1W9/20:3W9)HMDB
DAG(40:4)HMDB
DG(20:1/20:3)HMDB
DG(20:1N9/20:3N9)HMDB
DG(20:1W9/20:3W9)HMDB
DG(40:4)HMDB
DiacylglycerolHMDB
Diacylglycerol(20:1/20:3)HMDB
Diacylglycerol(20:1n9/20:3n9)HMDB
Diacylglycerol(20:1W9/20:3W9)HMDB
Diacylglycerol(40:4)HMDB
DiglycerideHMDB
1-(11-Eicosenoyl)-2-(5Z,8Z,11Z-eicosatrienoyl)-sn-glycerolHMDB
DG(20:1(11Z)/20:3(5Z,8Z,11Z)/0:0)Lipid Annotator
Chemical FormulaC43H76O5
Average Molecular Weight673.0605
Monoisotopic Molecular Weight672.569275542
IUPAC Name(2S)-1-hydroxy-3-[(11Z)-icos-11-enoyloxy]propan-2-yl (5Z,8Z,11Z)-icosa-5,8,11-trienoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCCCC\C=C/CCCCCCCC)OC(=O)CCC\C=C/C\C=C/C\C=C/CCCCCCCC
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/h17-20,24,26,30,32,41,44H,3-16,21-23,25,27-29,31,33-40H2,1-2H3/b19-17-,20-18-,26-24-,32-30-/t41-/m0/s1
InChI KeyXNHZTAPDVIWTFP-MTVOCPQASA-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
logP10.41ALOGPS
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
Polarizability87.26 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, Positivesplash10-0313-1195152000-a274f75c7ffe5b76a2e4View 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, Positivesplash10-07ou-1049006000-6cae21102cd403ff4f27View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0693-3097043000-3f861c2800d35c8ddd50View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbd-1094242000-6a4b7bf710fa7b049f7eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0abc-0049003000-fa0263aec0595bac12eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-1049001000-9982ea59a3544fe40f7bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3059000000-2458e4f5be51600fe573View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fr-1009006000-97f9957805541d5c69f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-3029000000-bca5b0a8bbe21ecf71b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-2039000000-f414dc00257b657b1077View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-2144029000-bd3a67cfc2ba34c2ab01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-3196011000-53ee2fbc8daadab09c41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06rl-3369000000-87ceb36dffb546406249View 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, Positivesplash10-000i-0009000000-0cc96865835bc2572d2aView 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, Positivesplash10-09k9-0009004000-5d92dcbd56dbb4ea85afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-04i3-0009004000-b7683857543eb39eff19View 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 IDHMDB0007400
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024593
KNApSAcK IDNot Available
Chemspider ID24766122
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53478214
PDB IDNot Available
ChEBI ID89056
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(20:1(11Z)/20:3(5Z,8Z,11Z)/0:0) → Cytidine monophosphate + PE(20:1(11Z)/20:3(5Z,8Z,11Z))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(20:1(11Z)/20:3(5Z,8Z,11Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(20:1(11Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(20:1(11Z)/20:3(5Z,8Z,11Z)/0:0) + Erucoyl-CoA → TG(20:1(11Z)/20:3(5Z,8Z,11Z)/22:1(13Z)) + Coenzyme Adetails
DG(20:1(11Z)/20:3(5Z,8Z,11Z)/0:0) + Clupanodonyl CoA → TG(20:1(11Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails