Showing metabocard for DG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0) (BMDB0007338)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:35:20 UTC
Update Date2020-05-21 16:27:57 UTC
BMDB IDBMDB0007338
Secondary Accession Numbers
  • BMDB07338
Metabolite Identification
Common NameDG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0)
DescriptionDG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0), also known as dg(18:4(6z,9z,12z,15z)/18:4(6z,9z,12z,15z)/0:0) or DAG(18:4/18:4), belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Thus, DG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0) is considered to be a diradylglycerol lipid molecule. DG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0) can be biosynthesized from PA(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)); which is catalyzed by the enzyme phosphatidate phosphatase. Furthermore, DG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0) and stearidonoyl-CoA can be converted into TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)); which is catalyzed by the enzyme dg(18:4(6z,9z,12z,15z)/18:4(6z,9z,12z,15z)/0:0) O-acyltransferase. Furthermore, DG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0) can be biosynthesized from PA(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)) through its interaction with the enzyme phosphatidate phosphatase. Furthermore, DG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0) and eicosatetraenoyl-CoA can be converted into TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)) through its interaction with the enzyme dg(18:4(6z,9z,12z,15z)/18:4(6z,9z,12z,15z)/0:0) O-acyltransferase. Furthermore, DG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0) can be biosynthesized from PA(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)) through the action of the enzyme phosphatidate phosphatase. Finally, DG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0) and adrenoyl-CoA can be converted into TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)); which is catalyzed by the enzyme dg(18:4(6z,9z,12z,15z)/18:4(6z,9z,12z,15z)/0:0) O-acyltransferase. In cattle, DG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0) is involved in several metabolic pathways, some of which include de novo triacylglycerol biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)) pathway, de novo triacylglycerol biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)) pathway, de novo triacylglycerol biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)) pathway, and de novo triacylglycerol biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2-Distearidonoyl-rac-glycerolHMDB
DAG(18:4/18:4)HMDB
DAG(18:4N3/18:4N3)HMDB
DAG(18:4W3/18:4W3)HMDB
DAG(36:8)HMDB
DG(18:4/18:4)HMDB
DG(18:4N3/18:4N3)HMDB
DG(18:4W3/18:4W3)HMDB
DG(36:8)HMDB
DiacylglycerolHMDB
Diacylglycerol(18:4/18:4)HMDB
Diacylglycerol(18:4n3/18:4n3)HMDB
Diacylglycerol(18:4W3/18:4W3)HMDB
Diacylglycerol(36:8)HMDB
DiglycerideHMDB
1,2-Di(6Z,9Z,12Z,15Z-octadecatetraenoyl)-rac-glycerolHMDB
DG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0)Lipid Annotator
Chemical FormulaC39H60O5
Average Molecular Weight608.8907
Monoisotopic Molecular Weight608.44407503
IUPAC Name(2S)-1-hydroxy-3-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]propan-2-yl (6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C39H60O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(41)43-36-37(35-40)44-39(42)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h5-8,11-14,17-20,23-26,37,40H,3-4,9-10,15-16,21-22,27-36H2,1-2H3/b7-5-,8-6-,13-11-,14-12-,19-17-,20-18-,25-23-,26-24-/t37-/m0/s1
InChI KeyZXBDMMYPYQQALX-BJXCJIDGSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassLineolic acids and derivatives
Direct ParentLineolic acids and derivatives
Alternative Parents
Substituents
  • Octadecanoid
  • 1,2-acyl-sn-glycerol
  • Diacylglycerol
  • Diradylglycerol
  • Fatty acid ester
  • Glycerolipid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Primary alcohol
  • 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
  • Cytoplasm
  • 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
logP8ALOGPS
logP10.89ChemAxon
logS-7.2ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count30ChemAxon
Refractivity195.04 m³·mol⁻¹ChemAxon
Polarizability73.36 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 (1 TMS) - 70eV, Positivesplash10-0pvi-5451914000-561caf442cfd62997e10View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("DG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000009000-d4526ce0de599a07374aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001l-0009063000-eebedfa5e1b0aa52e08eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003r-0009017000-61e78816d19269b8f846View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000009000-7df180102dd87d77a63eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000009000-7df180102dd87d77a63eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0019001000-c3696cbf1ff8a39a3c54View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1023093000-bffe894a60374d459dd6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-5197050000-cab489afe530e36e635fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-0392110000-c641eea01373d61b45ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000009000-86f2dd8797e9e8907ea2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001l-0009063000-2cccebffc54bac412517View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003r-0009017000-fae3ea3b53db9b5f454eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0066009000-3e37ecb85e145782ba5dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05di-5095000000-b624c8e4b7fa5eb09385View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-3090000000-e51b946ee93184e73077View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • 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 IDHMDB0007338
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024531
KNApSAcK IDNot Available
Chemspider ID24766075
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53478167
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(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0) → Cytidine monophosphate + PE(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))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(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0) + Clupanodonyl CoA → TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails