Showing metabocard for DG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0) (BMDB0007404)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:36:40 UTC
Update Date2020-05-21 16:28:00 UTC
BMDB IDBMDB0007404
Secondary Accession Numbers
  • BMDB07404
Metabolite Identification
Common NameDG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0)
DescriptionDG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0)[iso2], also known as dg(20:1(11z)/20:5(5z,8z,11z,14z,17z)/0:0)[iso2] or DAG(20:1/20:5), belongs to the class of organic compounds known as 1,2-dg(20:1(11z)/20:5(5z,8z,11z,14z,17z)/0:0)[iso2]s. These are dg(20:1(11z)/20:5(5z,8z,11z,14z,17z)/0:0)[iso2]s containing a glycerol acylated at positions 1 and 2. Thus, DG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0)[iso2] is considered to be a diradylglycerol lipid molecule. DG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0)[iso2] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, DG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0)[iso2] is involved in a couple of metabolic pathways, which include de novo triacylglycerol biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0) pathway and de novo triacylglycerol biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Eicosenoyl-2-eicosapentaenoyl-sn-glycerolHMDB
DAG(20:1/20:5)HMDB
DAG(20:1N9/20:5N3)HMDB
DAG(20:1W9/20:5W3)HMDB
DAG(40:6)HMDB
DG(20:1/20:5)HMDB
DG(20:1N9/20:5N3)HMDB
DG(20:1W9/20:5W3)HMDB
DG(40:6)HMDB
DiacylglycerolHMDB
Diacylglycerol(20:1/20:5)HMDB
Diacylglycerol(20:1n9/20:5n3)HMDB
Diacylglycerol(20:1W9/20:5W3)HMDB
Diacylglycerol(40:6)HMDB
DiglycerideHMDB
1-(11-Eicosenoyl)-2-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycerolHMDB
DG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0)Lipid Annotator
Chemical FormulaC43H72O5
Average Molecular Weight669.0288
Monoisotopic Molecular Weight668.537975414
IUPAC Name(2S)-1-hydroxy-3-[(11Z)-icos-11-enoyloxy]propan-2-yl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
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/C\C=C/C\C=C/CC
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/h6,8,12,14,17-20,24,26,30,32,41,44H,3-5,7,9-11,13,15-16,21-23,25,27-29,31,33-40H2,1-2H3/b8-6-,14-12-,19-17-,20-18-,26-24-,32-30-/t41-/m0/s1
InChI KeyKXSTZGDSFQAWPR-KFALEISNSA-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
logP9.73ALOGPS
logP13.39ChemAxon
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 Count36ChemAxon
Refractivity211.21 m³·mol⁻¹ChemAxon
Polarizability83.83 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, Positivesplash10-069c-3294101000-43c84911dd4dd37257efView 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, Positivesplash10-014r-1089006000-954dcd2177bf87a7d572View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gbl-2094001000-e6f86e5f92b57ad7b139View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-1093020000-eab3eefeb7eef25a152aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-066u-0059003000-e92b5373dbbc8e385803View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1059001000-7fda7c18d192a722c6ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-4069000000-33901b8e90377b9fd7fbView 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, Positivesplash10-0ldi-0009004000-c4b3c2785ba4c9cfa10bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0670-0009004000-ac90f72f7e45eb957395View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0008009000-4e38750cd3ee2a0dfbc3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-3029001000-456b4fc03ba1daed6634View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-4059000000-69a491879894a5022352View 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-e9e31557a66bffa64e9cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-1095047000-811efedf69aed90e8dc0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1193010000-040448323cbe62e7e854View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1298000000-a8c637a3281dab997919View 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 IDHMDB0007404
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024597
KNApSAcK IDNot Available
Chemspider ID7822803
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543853
PDB IDNot Available
ChEBI ID89055
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)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0) → Cytidine monophosphate + PE(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))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)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0) + Erucoyl-CoA → TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)) + Coenzyme Adetails
DG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0) + Clupanodonyl CoA → TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails