Showing metabocard for DG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/0:0) (BMDB0007250)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:33:35 UTC
Update Date2020-05-21 16:27:53 UTC
BMDB IDBMDB0007250
Secondary Accession Numbers
  • BMDB07250
Metabolite Identification
Common NameDG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/0:0)
DescriptionDG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/0:0)[iso2], also known as dg(18:2(9z,12z)/18:3(9z,12z,15z)/0:0)[iso2] or DAG(18:2/18:3), 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. Thus, DG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/0:0)[iso2] is considered to be a diradylglycerol lipid molecule. DG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/0:0)[iso2] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, DG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/0:0)[iso2] is involved in several metabolic pathways, some of which include de novo triacylglycerol biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)) pathway, de novo triacylglycerol biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:0) pathway, de novo triacylglycerol biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/24:0) pathway, and phosphatidylethanolamine biosynthesis pe(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Diacylglycerol(18:2/18:3)HMDB
DG(36:5)HMDB
DiglycerideHMDB
1-Linoleoyl-2-a-linolenoyl-sn-glycerolHMDB
Diacylglycerol(36:5)HMDB
DAG(18:2/18:3)HMDB
DAG(36:5)HMDB
DiacylglycerolHMDB
DG(18:2/18:3)HMDB
1-(9Z,12Z-Octadecadienoyl)-2-(9Z,12Z,15Z-octadeatrienoyl)-sn-glycerolHMDB
DG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/0:0)Lipid Annotator
Chemical FormulaC39H66O5
Average Molecular Weight614.9383
Monoisotopic Molecular Weight614.491025222
IUPAC Name(2S)-1-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propan-2-yl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C39H66O5/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/h6,8,11-14,17-20,37,40H,3-5,7,9-10,15-16,21-36H2,1-2H3/b8-6-,13-11-,14-12-,19-17-,20-18-/t37-/m0/s1
InChI KeyPGXBELQFNRPKBC-WBVIKXMWSA-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
logP9.24ALOGPS
logP11.97ChemAxon
logS-7.6ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count33ChemAxon
Refractivity191.69 m³·mol⁻¹ChemAxon
Polarizability76.63 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, Positivesplash10-074r-6491524000-01635bcc14ee161d88cbView 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)/18:3(9Z,12Z,15Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000009000-4c32905bafde13e60792View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0009031000-953704fe46b24ac587e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0009003000-d24533feb2f3500f51f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000009000-76503681101bfbcc5bcfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0009031000-388c05f1d1934f435fa8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0009003000-e79330b37c9a60c83a79View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0imi-3096007000-5251e469ed02d9db2211View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-4093000000-d1c2ccc11ac21328dd4eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-2091000000-723bcdc8972d8802978fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-3254195000-e463777d7613f6e2fcbeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dr-3395130000-fd09cea5734aa70471b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dr-1295000000-d4d33428565c018cb523View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000009000-c292a667c0eda7d86f41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000009000-c292a667c0eda7d86f41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0009000000-80ff7186e16d1afeb6cbView 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 IDHMDB0007250
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 Compound9543737
PDB IDNot Available
ChEBI ID89198
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)/18:3(9Z,12Z,15Z)/0:0) → Cytidine monophosphate + PE(18:2(9Z,12Z)/18:3(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)/18:3(9Z,12Z,15Z)/0:0) + Eicosanoyl-CoA → TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:0) + Coenzyme Adetails
DG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/0:0) + Gondoyl-CoA → TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(11Z))[iso6] + Coenzyme Adetails
DG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/0:0) + Docosanoyl-CoA → TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:0) + Coenzyme Adetails
DG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/0:0) + Erucoyl-CoA → TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:1(13Z)) + Coenzyme Adetails
DG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/0:0) + Clupanodonyl CoA → TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails