Showing metabocard for DG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/0:0) (BMDB0007523)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:39:04 UTC
Update Date2020-05-21 16:28:04 UTC
BMDB IDBMDB0007523
Secondary Accession Numbers
  • BMDB07523
Metabolite Identification
Common NameDG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/0:0)
DescriptionDG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/0:0)[iso2], also known as DAG(20:4/22:2) or dg(20:4(5z,8z,11z,14z)/22:2(13z,16z)/0:0)[iso2], belongs to the class of organic compounds known as 1,2-dg(20:4(5z,8z,11z,14z)/22:2(13z,16z)/0:0)[iso2]s. These are dg(20:4(5z,8z,11z,14z)/22:2(13z,16z)/0:0)[iso2]s containing a glycerol acylated at positions 1 and 2. Thus, DG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/0:0)[iso2] is considered to be a diradylglycerol lipid molecule. DG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/0:0)[iso2] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, DG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/0:0)[iso2] is involved in a couple of metabolic pathways, which include de novo triacylglycerol biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) pathway and de novo triacylglycerol biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DAG(20:4/22:2)HMDB
DG(42:6)HMDB
DiglycerideHMDB
Diacylglycerol(42:6)HMDB
DG(20:4/22:2)HMDB
DiacylglycerolHMDB
DAG(42:6)HMDB
1-Arachidonoyl-2-docosadienoyl-sn-glycerolHMDB
1-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-2-(13Z,16Z-docosadienoyl)-sn-glycerolHMDB
Diacylglycerol(20:4/22:2)HMDB
DG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/0:0)Lipid Annotator
Chemical FormulaC45H76O5
Average Molecular Weight697.0819
Monoisotopic Molecular Weight696.569275542
IUPAC Name(2S)-1-hydroxy-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propan-2-yl (13Z,16Z)-docosa-13,16-dienoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CCCCCCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C45H76O5/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/h11-14,17-20,25,27,31,33,43,46H,3-10,15-16,21-24,26,28-30,32,34-42H2,1-2H3/b13-11-,14-12-,19-17-,20-18-,27-25-,33-31-/t43-/m0/s1
InChI KeyVKEYYLBMEUEXFX-HFPOVAENSA-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
logP10.05ALOGPS
logP14.28ChemAxon
logS-7.9ALOGPS
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
Refractivity220.41 m³·mol⁻¹ChemAxon
Polarizability88.15 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, Positivesplash10-03di-0000000900-4d1a8fb2902d0b1a9641View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fu-0009003000-ba5028dbb88ca80d4cc2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-0009001300-eb29a5beb4e9e00e13a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000000900-8a1c6226c0719bd2dacdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000000900-8a1c6226c0719bd2dacdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0159-0009600100-8c5e518eab24b2248f54View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1009006000-78987024dbb216331da4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uki-4019000000-a4c3f9e08f024cf9c346View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-3019000000-7ca51e5960f1e697b1b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00mk-5238049000-305bef295aba4fb198f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1129000000-ddb3e83e89b0240c5379View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-3439000000-159631269514eaa38a12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000900-0e123f184b57ffebfcd6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fu-0009003000-7bc6b9d167fdb945d7fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-0009001300-9c96452b7e76abe0774eView 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 IDHMDB0007523
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 Compound9543926
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(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/0:0) → Cytidine monophosphate + PE(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))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(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/0:0) + Clupanodonyl CoA → TG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails