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Record Information
Version1.0
Creation Date2016-09-30 23:31:58 UTC
Update Date2020-05-21 16:27:47 UTC
BMDB IDBMDB0007170
Secondary Accession Numbers
  • BMDB07170
Metabolite Identification
Common NameDG(18:0/20:4(5Z,8Z,11Z,14Z)/0:0)
DescriptionDG(18:0/20:4(5Z,8Z,11Z,14Z)/0:0), also known as DAG(18:0/20:4) or Dg(18:0/20:4(5z,8z,11z,14z)/0:0), belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2. Thus, DG(18:0/20:4(5Z,8Z,11Z,14Z)/0:0) is considered to be a diradylglycerol lipid molecule. DG(18:0/20:4(5Z,8Z,11Z,14Z)/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(18:0/20:4(5Z,8Z,11Z,14Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, CDP-Ethanolamine and DG(18:0/20:4(5Z,8Z,11Z,14Z)/0:0) can be converted into cytidine monophosphate and PE(18:0/20:4(5Z,8Z,11Z,14Z)) through the action of the enzyme choline/ethanolaminephosphotransferase. In addition, CDP-Choline and DG(18:0/20:4(5Z,8Z,11Z,14Z)/0:0) can be converted into cytidine monophosphate and PC(18:0/20:4(5Z,8Z,11Z,14Z)); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. In cattle, DG(18:0/20:4(5Z,8Z,11Z,14Z)/0:0) is involved in the metabolic pathway called phosphatidylcholine biosynthesis PC(18:0/20:4(5Z,8Z,11Z,14Z)) pathway.
Structure
Thumb
Synonyms
ValueSource
(2S)-1-Hydroxy-3-(stearoyloxy)propan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoateHMDB
1-Octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerolHMDB
1-Stearoyl-2-arachidonoylglycerolHMDB
DAG(18:0/20:4)HMDB
DAG(18:0/20:4OMEGA6)HMDB
DAG(38:4)HMDB
DG(18:0/20:4(5Z,8Z,11Z,14Z)/0:0)[iso2]HMDB
DG(18:0/20:4(OMEGA-6)/0:0)HMDB
DG(18:0/20:4)HMDB
DG(18:0/20:4/0:0)[iso2]HMDB
DG(18:0/20:4OMEGA6)HMDB
DG(38:4)HMDB
Diacylglycerol(18:0/20:4)HMDB
Diacylglycerol(18:0/20:4omega6)HMDB
Diacylglycerol(38:4)HMDB
(2S)-1-Hydroxy-3-(stearoyloxy)propan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acidHMDB
1-Stearoyl-2-arachidonoyl-sn-glycerolHMDB
DAG(18:0/20:4N6)HMDB
DAG(18:0/20:4W6)HMDB
DG(18:0/20:4N6)HMDB
DG(18:0/20:4W6)HMDB
DiacylglycerolHMDB
Diacylglycerol(18:0/20:4n6)HMDB
Diacylglycerol(18:0/20:4W6)HMDB
DiglycerideHMDB
DG(18:0/20:4(5Z,8Z,11Z,14Z)/0:0)Lipid Annotator
Chemical FormulaC41H72O5
Average Molecular Weight645.0074
Monoisotopic Molecular Weight644.537975414
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number65914-84-3
SMILESNot Available
InChI Identifier
InChI=1S/C41H72O5/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-41(44)46-39(37-42)38-45-40(43)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h11,13,17,19,22,24,28,30,39,42H,3-10,12,14-16,18,20-21,23,25-27,29,31-38H2,1-2H3/b13-11-,19-17-,24-22-,30-28-/t39-/m0/s1
InChI KeyNSXLMTYRMFVYNT-IUJDHQGTSA-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 PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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 IDHMDB0007170
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024364
KNApSAcK IDNot Available
Chemspider ID4943054
KEGG Compound IDC00165
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6438587
PDB IDNot Available
ChEBI ID75728
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

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(18:0/20:4(5Z,8Z,11Z,14Z)/0:0) → Cytidine monophosphate + PE(18:0/20:4(5Z,8Z,11Z,14Z))details
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(18:0/20:4(5Z,8Z,11Z,14Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails