Showing metabocard for DG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/0:0) (BMDB0007431)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:37:12 UTC
Update Date2020-05-21 16:28:01 UTC
BMDB IDBMDB0007431
Secondary Accession Numbers
  • BMDB07431
Metabolite Identification
Common NameDG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/0:0)
DescriptionDG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/0:0)[iso2], also known as dg(20:2(11z,14z)/20:4(5z,8z,11z,14z)/0:0)[iso2] or DAG(20:2/20:4), belongs to the class of organic compounds known as 1,2-dg(20:2(11z,14z)/20:4(5z,8z,11z,14z)/0:0)[iso2]s. These are dg(20:2(11z,14z)/20:4(5z,8z,11z,14z)/0:0)[iso2]s containing a glycerol acylated at positions 1 and 2. Thus, DG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/0:0)[iso2] is considered to be a diradylglycerol lipid molecule. DG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/0:0)[iso2] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, DG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/0:0)[iso2] is involved in several metabolic pathways, some of which include de novo triacylglycerol biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/24:0) pathway, de novo triacylglycerol biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:0) pathway, de novo triacylglycerol biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z)) pathway, and de novo triacylglycerol biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Eicosadienoyl-2-arachidonoyl-sn-glycerolHMDB
DAG(20:2/20:4)HMDB
DAG(20:2N6/20:4N6)HMDB
DAG(20:2W6/20:4W6)HMDB
DAG(40:6)HMDB
DG(20:2/20:4)HMDB
DG(20:2N6/20:4N6)HMDB
DG(20:2W6/20:4W6)HMDB
DG(40:6)HMDB
DiacylglycerolHMDB
Diacylglycerol(20:2/20:4)HMDB
Diacylglycerol(20:2n6/20:4n6)HMDB
Diacylglycerol(20:2W6/20:4W6)HMDB
Diacylglycerol(40:6)HMDB
DiglycerideHMDB
1-(11Z,14Z-Eicosadienoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerolHMDB
DG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/0:0)Lipid Annotator
Chemical FormulaC43H72O5
Average Molecular Weight669.0288
Monoisotopic Molecular Weight668.537975414
IUPAC Name(2S)-1-hydroxy-3-[(11Z,14Z)-icosa-11,14-dienoyloxy]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)CCCCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C43H72O5/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/h11-14,17-20,24,26,30,32,41,44H,3-10,15-16,21-23,25,27-29,31,33-40H2,1-2H3/b13-11-,14-12-,19-17-,20-18-,26-24-,32-30-/t41-/m0/s1
InChI KeyXWQMGVSLXBIWRI-SXIWVUKCSA-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
logP9.68ALOGPS
logP13.39ChemAxon
logS-7.7ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count36ChemAxon
Refractivity211.21 m³·mol⁻¹ChemAxon
Polarizability84.07 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, Positivesplash10-03di-1295133000-669ce4a538900609f1a2View 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, Positivesplash10-014i-1049015000-d352e0019381e428970eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0296-3098053000-7321cf712b788d22d4a0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-2094251000-126eb578615669057701View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ap0-0039003000-00e2b0f93a7015bd9479View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1049000000-7c3893cdbced2e9105baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3059000000-d03d15d6816554aaf8d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000009000-d8fc180957e9e2b5f8d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000009000-d8fc180957e9e2b5f8d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001r-0009000000-039b12d2021efbfb41d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0i09-5296068000-d5414c464442a7f49453View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-2294010000-74bd6bc8a88144559ba5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06ri-3298010000-82c5c1655ab70b377227View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1019008000-5de7e7f23f7cc076f152View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-4029000000-db16b38766d8a6fb1e0bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3039000000-0fdd4187868be627d88dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000009000-e2329eb25be3f42c3a5dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0i00-0009004000-8532eded8bef1ece3508View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02ti-0009004000-33cfe68e362aedcb64f6View 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 IDHMDB0007431
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024624
KNApSAcK IDNot Available
Chemspider ID7822802
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543852
PDB IDNot Available
ChEBI ID89045
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(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/0:0) → Cytidine monophosphate + PE(20:2(11Z,14Z)/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(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(20:2n6/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/0:0) + Clupanodonyl CoA → TG(20:2n6/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails