Showing metabocard for DG(20:3(5Z,8Z,11Z)/22:0/0:0) (BMDB0007463)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:37:51 UTC
Update Date2020-05-21 16:28:02 UTC
BMDB IDBMDB0007463
Secondary Accession Numbers
  • BMDB07463
Metabolite Identification
Common NameDG(20:3(5Z,8Z,11Z)/22:0/0:0)
DescriptionDG(20:3(5Z,8Z,11Z)/22:0/0:0), also known as dg(20:3(5z,8z,11z)/22:0/0:0) or DAG(20:3/22:0), belongs to the class of organic compounds known as 1,2-dg(20:3(5z,8z,11z)/22:0/0:0)s. These are dg(20:3(5z,8z,11z)/22:0/0:0)s containing a glycerol acylated at positions 1 and 2. DG(20:3(5Z,8Z,11Z)/22:0/0:0) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). DG(20:3(5Z,8Z,11Z)/22:0/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(20:3(5Z,8Z,11Z)/22:0/0:0) can be biosynthesized from PA(20:3(5Z,8Z,11Z)/22:0); which is catalyzed by the enzyme phosphatidate phosphatase. Furthermore, DG(20:3(5Z,8Z,11Z)/22:0/0:0) and docosadienoyl-CoA can be converted into TG(20:3(5Z,8Z,11Z)/22:0/22:2(13Z,16Z)) through the action of the enzyme dg(20:3(5z,8z,11z)/22:0/0:0) O-acyltransferase. Furthermore, DG(20:3(5Z,8Z,11Z)/22:0/0:0) can be biosynthesized from PA(20:3(5Z,8Z,11Z)/22:0) through its interaction with the enzyme phosphatidate phosphatase. Finally, DG(20:3(5Z,8Z,11Z)/22:0/0:0) and osbondoyl-CoA can be converted into TG(20:3(5Z,8Z,11Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z)) through its interaction with the enzyme dg(20:3(5z,8z,11z)/22:0/0:0) O-acyltransferase. In cattle, DG(20:3(5Z,8Z,11Z)/22:0/0:0) is involved in a couple of metabolic pathways, which include de novo triacylglycerol biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/22:2(13Z,16Z)) pathway and de novo triacylglycerol biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Meadoyl-2-behenoyl-sn-glycerolHMDB
DAG(20:3/22:0)HMDB
DAG(20:3N9/22:0)HMDB
DAG(20:3W9/22:0)HMDB
DAG(42:3)HMDB
DG(20:3/22:0)HMDB
DG(20:3N9/22:0)HMDB
DG(20:3W9/22:0)HMDB
DG(42:3)HMDB
DiacylglycerolHMDB
Diacylglycerol(20:3/22:0)HMDB
Diacylglycerol(20:3n9/22:0)HMDB
Diacylglycerol(20:3W9/22:0)HMDB
Diacylglycerol(42:3)HMDB
DiglycerideHMDB
1-(5Z,8Z,11Z-Eicosatrienoyl)-2-docosanoyl-sn-glycerolHMDB
DG(20:3(5Z,8Z,11Z)/22:0/0:0)Lipid Annotator
Chemical FormulaC45H82O5
Average Molecular Weight703.1296
Monoisotopic Molecular Weight702.616225734
IUPAC Name(2S)-1-hydroxy-3-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propan-2-yl docosanoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCC\C=C/C\C=C/C\C=C/CCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C45H82O5/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/h18,20,25,27,31,33,43,46H,3-17,19,21-24,26,28-30,32,34-42H2,1-2H3/b20-18-,27-25-,33-31-/t43-/m0/s1
InChI KeyZEHUKAZVLGGOII-VTXASNIHSA-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
logP10.75ALOGPS
logP15.36ChemAxon
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 Count41ChemAxon
Refractivity217.06 m³·mol⁻¹ChemAxon
Polarizability93.24 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, Negativesplash10-0udi-1009000700-5f3e867817071b74ac33View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05g0-2009000000-b186127a0679637ed548View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-2019000000-6e7939edf3ce3e0f1928View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000000900-b20fb29c74200eb98819View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dt-0009003100-258cdc9caff53fa0e43bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03kb-0009000300-51e5245bcaed57ec954fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000900-dc58ed4880ceba2a5802View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000000900-dc58ed4880ceba2a5802View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0150-0009600100-d927304ca1c113191c36View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-1119011300-22ab31de011da095f840View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-3029000000-0c2fe5d64096b6c1dc89View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-4938000000-d7885eef78ac3d09a6f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000000900-f6417bf3893e2e9d6b11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dt-0009003100-1a14f6fb8ac7a70b4158View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03kb-0009000300-a539f16ec656e5e91b4eView 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 IDHMDB0007463
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024656
KNApSAcK IDNot Available
Chemspider ID24766166
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53478258
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(20:3(5Z,8Z,11Z)/22:0/0:0) → Cytidine monophosphate + PE(20:3(5Z,8Z,11Z)/22:0)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)/22:0/0:0) + Erucoyl-CoA → TG(20:3(5Z,8Z,11Z)/22:0/22:1(13Z)) + Coenzyme Adetails
DG(20:3(5Z,8Z,11Z)/22:0/0:0) + Clupanodonyl CoA → TG(20:3(5Z,8Z,11Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails