Showing metabocard for DG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/0:0) (BMDB0007251)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:33:36 UTC
Update Date2020-05-21 16:27:53 UTC
BMDB IDBMDB0007251
Secondary Accession Numbers
  • BMDB07251
Metabolite Identification
Common NameDG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/0:0)
DescriptionDG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/0:0), also known as DAG(18:2/18:4) or dg(18:2(9z,12z)/18:4(6z,9z,12z,15z)/0:0), 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(18:2(9Z,12Z)/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(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/0:0) can be biosynthesized from PA(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)); which is mediated by the enzyme phosphatidate phosphatase. Furthermore, DG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/0:0) and erucoyl-CoA can be converted into TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z)); which is mediated by the enzyme dg(18:2(9z,12z)/18:4(6z,9z,12z,15z)/0:0) O-acyltransferase. Furthermore, DG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/0:0) can be biosynthesized from PA(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)); which is mediated by the enzyme phosphatidate phosphatase. Furthermore, DG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/0:0) and nervonoyl-CoA can be converted into TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z)); which is mediated by the enzyme dg(18:2(9z,12z)/18:4(6z,9z,12z,15z)/0:0) O-acyltransferase. Furthermore, DG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/0:0) can be biosynthesized from PA(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)); which is mediated by the enzyme phosphatidate phosphatase. Finally, DG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/0:0) and gondoyl-CoA can be converted into TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z)); which is mediated by the enzyme dg(18:2(9z,12z)/18:4(6z,9z,12z,15z)/0:0) O-acyltransferase. In cattle, DG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/0:0) is involved in several metabolic pathways, some of which include de novo triacylglycerol biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z)) pathway, de novo triacylglycerol biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z)) pathway, de novo triacylglycerol biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z)) pathway, and de novo triacylglycerol biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DAG(18:2/18:4)HMDB
DiglycerideHMDB
Diacylglycerol(36:6)HMDB
Diacylglycerol(18:2/18:4)HMDB
DG(36:6)HMDB
1-Linoleoyl-2-stearidonoyl-sn-glycerolHMDB
DG(18:2/18:4)HMDB
DiacylglycerolHMDB
1-(9Z,12Z-Octadecadienoyl)-2-(6Z,9Z,12Z,15Z-octadecatetraenoyl)-sn-glycerolHMDB
DAG(36:6)HMDB
DG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/0:0)Lipid Annotator
Chemical FormulaC39H64O5
Average Molecular Weight612.9225
Monoisotopic Molecular Weight612.475375158
IUPAC Name(2S)-1-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]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/CCCCC)OC(=O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C39H64O5/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/h6,8,11-14,17-20,24,26,37,40H,3-5,7,9-10,15-16,21-23,25,27-36H2,1-2H3/b8-6-,13-11-,14-12-,19-17-,20-18-,26-24-/t37-/m0/s1
InChI KeyBYLXXZYUDXCZFN-YQRUEVQWSA-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
logP8.64ALOGPS
logP11.61ChemAxon
logS-7.5ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count32ChemAxon
Refractivity192.8 m³·mol⁻¹ChemAxon
Polarizability75 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, Positivesplash10-0cki-5490304000-beaef068a92a78b8c78cView 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(18:2(9Z,12Z)/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, Positivesplash10-001i-0000009000-41ed6867d946c515aebaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001s-0009031000-0e5b618c69b80653d182View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001r-0009003000-1a9bcc62ba63d8c36aa1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000009000-3d8ea9f544e62fbb777cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001s-0009031000-5dd05314fa704c2d8f7fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001r-0009003000-1a59098281383f4a2318View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1055009000-4b5140af07bd1227e1a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0200-5094000000-ad1542f72e0deccfa697View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-2090000000-a24bbdb6f1de40fbd2b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000009000-615a30fbd964efd1b181View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000009000-615a30fbd964efd1b181View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0009000000-f23ea979506c152e17c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08fr-3266195000-e58dc2fee19c21cd97f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-3696020000-c37088f968c73e8f2d91View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0560-1395000000-98c011107d0a5335e80bView 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 IDHMDB0007251
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024444
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53478106
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(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/0:0) → Cytidine monophosphate + PE(18:2(9Z,12Z)/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(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/0:0) + Eicosanoyl-CoA → TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:0)[iso6] + Coenzyme Adetails
DG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/0:0) + Clupanodonyl CoA → TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails