Showing metabocard for DG(18:0/18:3(6Z,9Z,12Z)/0:0) (BMDB0007162)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:31:49 UTC
Update Date2020-05-21 16:27:46 UTC
BMDB IDBMDB0007162
Secondary Accession Numbers
  • BMDB07162
Metabolite Identification
Common NameDG(18:0/18:3(6Z,9Z,12Z)/0:0)
DescriptionDG(18:0/18:3(6Z,9Z,12Z)/0:0), also known as dg(18:0/18:3(6z,9z,12z)/0:0) or DAG(18:0/18:3), 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(18:0/18:3(6Z,9Z,12Z)/0:0) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). DG(18:0/18:3(6Z,9Z,12Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(18:0/18:3(6Z,9Z,12Z)/0:0) can be biosynthesized from PA(18:0/18:3(6Z,9Z,12Z)) through its interaction with the enzyme phosphatidate phosphatase. In addition, DG(18:0/18:3(6Z,9Z,12Z)/0:0) and gamma-linolenoyl-CoA can be converted into TG(18:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)); which is mediated by the enzyme dg(18:0/18:3(6z,9z,12z)/0:0) O-acyltransferase. In cattle, DG(18:0/18:3(6Z,9Z,12Z)/0:0) is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DG(36:3)HMDB
DAG(36:3)HMDB
Diacylglycerol(18:0/18:3)HMDB
DiglycerideHMDB
DAG(18:0/18:3)HMDB
DG(18:0/18:3)HMDB
DiacylglycerolHMDB
1-Stearoyl-2-g-linolenoyl-sn-glycerolHMDB
1-Octadecanoyl-2-(6Z,9Z,12Z-octadecatrienoyl)-sn-glycerolHMDB
Diacylglycerol(36:3)HMDB
DG(18:0/18:3(6Z,9Z,12Z)/0:0)Lipid Annotator
Chemical FormulaC39H70O5
Average Molecular Weight618.9701
Monoisotopic Molecular Weight618.52232535
IUPAC Name(2S)-1-hydroxy-3-(octadecanoyloxy)propan-2-yl (6Z,9Z,12Z)-octadeca-6,9,12-trienoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C39H70O5/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/h12,14,18,20,24,26,37,40H,3-11,13,15-17,19,21-23,25,27-36H2,1-2H3/b14-12-,20-18-,26-24-/t37-/m0/s1
InChI KeyUZECZIKHMHALLK-AXXSQWPMSA-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
logP10.14ALOGPS
logP12.7ChemAxon
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 Count35ChemAxon
Refractivity189.45 m³·mol⁻¹ChemAxon
Polarizability79.45 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, Positivesplash10-0470-4390305000-3d8d39d181a052ac83fdView 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(18:0/18:3(6Z,9Z,12Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000009000-8739cce7a1cf023acbb4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f7c-0009004000-89ab69e2bb962a6bebcfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-0009004000-122a6dbf337cd63da07cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000009000-643d38840e80b534f39cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000009000-643d38840e80b534f39cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bt9-0009000000-408d13ba58bf20e8f4f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-3057229000-616279b61253069a85deView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0309-6196011000-9be3b6fae20e482d0d46View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-092i-6297000000-ad60af0f5ce6f9dbd5d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000009000-16faae87ea495f60500aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f7c-0009004000-e471ed82e887b03390a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-0009004000-99fb2386c4d130335aefView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0159-2066009000-c705a0c67249c767c292View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2092000000-73c34834d32dd90a0f75View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00o0-1090000000-31eda9d9137b04d28358View 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 IDHMDB0007162
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 Compound53478050
PDB IDNot Available
ChEBI ID88511
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(18:0/18:3(6Z,9Z,12Z)/0:0) → Cytidine monophosphate + PE(18:0/18:3(6Z,9Z,12Z))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(18:0/18:3(6Z,9Z,12Z)/0:0) + Gamma-linolenoyl-CoA → TG(18:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))[iso3] + Coenzyme Adetails
DG(18:0/18:3(6Z,9Z,12Z)/0:0) + Eicosanoyl-CoA → TG(18:0/18:3(6Z,9Z,12Z)/20:0) + Coenzyme Adetails
DG(18:0/18:3(6Z,9Z,12Z)/0:0) + Gondoyl-CoA → TG(18:0/18:3(6Z,9Z,12Z)/20:1(11Z)) + Coenzyme Adetails
DG(18:0/18:3(6Z,9Z,12Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(18:0/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(18:0/18:3(6Z,9Z,12Z)/0:0) + Docosanoyl-CoA → TG(18:0/18:3(6Z,9Z,12Z)/22:0) + Coenzyme Adetails
DG(18:0/18:3(6Z,9Z,12Z)/0:0) + Erucoyl-CoA → TG(18:0/18:3(6Z,9Z,12Z)/22:1(13Z)) + Coenzyme Adetails
DG(18:0/18:3(6Z,9Z,12Z)/0:0) + Clupanodonyl CoA → TG(18:0/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails
DG(18:0/18:3(6Z,9Z,12Z)/0:0) + Tetracosanoyl-CoA → TG(18:0/18:3(6Z,9Z,12Z)/24:0) + Coenzyme Adetails