Showing metabocard for DG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0) (BMDB0007309)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:34:46 UTC
Update Date2020-05-21 16:27:56 UTC
BMDB IDBMDB0007309
Secondary Accession Numbers
  • BMDB07309
Metabolite Identification
Common NameDG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0)
DescriptionDG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0), also known as dg(18:3(9z,12z,15z)/18:4(6z,9z,12z,15z)/0:0) or DAG(18:3/18:4), 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. DG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). DG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0) can be biosynthesized from PA(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)) through the action of the enzyme phosphatidate phosphatase. Furthermore, DG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0) and gondoyl-CoA can be converted into TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z)); which is catalyzed by the enzyme dg(18:3(9z,12z,15z)/18:4(6z,9z,12z,15z)/0:0) O-acyltransferase. Furthermore, DG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0) can be biosynthesized from PA(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)) through the action of the enzyme phosphatidate phosphatase. Furthermore, DG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0) and meadoyl-CoA can be converted into TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)) through the action of the enzyme dg(18:3(9z,12z,15z)/18:4(6z,9z,12z,15z)/0:0) O-acyltransferase. Furthermore, DG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0) can be biosynthesized from PA(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)) through its interaction with the enzyme phosphatidate phosphatase. Finally, DG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0) and docosanoyl-CoA can be converted into TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:0); which is mediated by the enzyme dg(18:3(9z,12z,15z)/18:4(6z,9z,12z,15z)/0:0) O-acyltransferase. In cattle, DG(18:3(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(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z)) pathway, de novo triacylglycerol biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)) pathway, de novo triacylglycerol biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:0) pathway, de novo triacylglycerol biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/24:0) pathway, and phosphatidylethanolamine biosynthesis pe(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Diacylglycerol(18:3/18:4)HMDB
Diacylglycerol(36:7)HMDB
DiglycerideHMDB
DG(36:7)HMDB
DiacylglycerolHMDB
1-a-Linolenoyl-2-stearidonoyl-sn-glycerolHMDB
DAG(18:3/18:4)HMDB
DAG(36:7)HMDB
1-(9Z,12Z,15Z-Octadeatrienoyl)-2-(6Z,9Z,12Z,15Z-octadecatetraenoyl)-sn-glycerolHMDB
DG(18:3/18:4)HMDB
DG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0)Lipid Annotator
Chemical FormulaC39H62O5
Average Molecular Weight610.9066
Monoisotopic Molecular Weight610.459725094
IUPAC Name(2S)-1-hydroxy-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]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)CCCCCCC\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/C39H62O5/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/h5-8,11-14,17-20,24,26,37,40H,3-4,9-10,15-16,21-23,25,27-36H2,1-2H3/b7-5-,8-6-,13-11-,14-12-,19-17-,20-18-,26-24-/t37-/m0/s1
InChI KeyLCDYTMCBCVVTIZ-FCPNELAOSA-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 DescriptorsNot Available
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
logP8.23ALOGPS
logP11.25ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count31ChemAxon
Refractivity193.92 m³·mol⁻¹ChemAxon
Polarizability74.05 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, Positivesplash10-0a59-5491514000-f96c8367e9b73dfd9c1eView 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(18:3(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-0000009000-9df7f7dd4679af62403cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0023-0009031000-d2db05920b4bac9cebeaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0049-0009003000-116a6ed825dd23b49f83View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000009000-bce7212637845afaf154View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0023-0009031000-3548245616aae049772bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0049-0009003000-186ef4b9318c7f1dd8cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0054009000-67bc17b81fe1234d161fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05di-5094000000-f55fc646dcc98321a01fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3090000000-813eeaae2dc634bf48abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1122093000-8a7d0154e61761fd7afaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-6298050000-02a49737f7ff7ec51b0eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05cr-1794000000-7e1549efe43b3d152b09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000009000-3559a8789a479959c1c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000009000-3559a8789a479959c1c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0009000000-cde4f4609ce273dc86adView 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 IDHMDB0007309
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024502
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53478150
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(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0) → Cytidine monophosphate + PE(18:3(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(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0) + Clupanodonyl CoA → TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails