Showing metabocard for DG(15:0/18:3(9Z,12Z,15Z)/0:0) (BMDB0007076)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:30:01 UTC
Update Date2020-05-21 16:27:32 UTC
BMDB IDBMDB0007076
Secondary Accession Numbers
  • BMDB07076
Metabolite Identification
Common NameDG(15:0/18:3(9Z,12Z,15Z)/0:0)
DescriptionDG(15:0/18:3(9Z,12Z,15Z)/0:0)[iso2], also known as dg(15:0/18:3(9z,12z,15z)/0:0)[iso2] or DAG(15:0/18:3), 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. Thus, DG(15:0/18:3(9Z,12Z,15Z)/0:0)[iso2] is considered to be a diradylglycerol lipid molecule. DG(15:0/18:3(9Z,12Z,15Z)/0:0)[iso2] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, DG(15:0/18:3(9Z,12Z,15Z)/0:0)[iso2] is involved in a couple of metabolic pathways, which include de novo triacylglycerol biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)) pathway and de novo triacylglycerol biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/20:2(11Z,14Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Pentadecanoyl-2-a-linolenoyl-sn-glycerolHMDB
1-Pentadecanoyl-2-alpha-linolenoyl-sn-glycerolHMDB
DAG(15:0/18:3)HMDB
DAG(15:0/18:3N3)HMDB
DAG(15:0/18:3W3)HMDB
DAG(33:3)HMDB
DG(15:0/18:3)HMDB
DG(15:0/18:3N3)HMDB
DG(15:0/18:3W3)HMDB
DG(33:3)HMDB
DiacylglycerolHMDB
Diacylglycerol(15:0/18:3)HMDB
Diacylglycerol(15:0/18:3n3)HMDB
Diacylglycerol(15:0/18:3W3)HMDB
Diacylglycerol(33:3)HMDB
DiglycerideHMDB
1-Pentadecanoyl-2-(9Z,12Z,15Z-octadeatrienoyl)-sn-glycerolHMDB
DG(15:0/18:3(9Z,12Z,15Z)/0:0)Lipid Annotator
Chemical FormulaC36H64O5
Average Molecular Weight576.8904
Monoisotopic Molecular Weight576.475375158
IUPAC Name(2S)-1-hydroxy-3-(pentadecanoyloxy)propan-2-yl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCCCCCCCCC)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C36H64O5/c1-3-5-7-9-11-13-15-17-18-19-21-23-25-27-29-31-36(39)41-34(32-37)33-40-35(38)30-28-26-24-22-20-16-14-12-10-8-6-4-2/h5,7,11,13,17-18,34,37H,3-4,6,8-10,12,14-16,19-33H2,1-2H3/b7-5-,13-11-,18-17-/t34-/m0/s1
InChI KeyUARHXHPRJDJCKE-QECOYPFHSA-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
logP9.57ALOGPS
logP11.36ChemAxon
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 Count32ChemAxon
Refractivity175.65 m³·mol⁻¹ChemAxon
Polarizability73.31 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, Positivesplash10-000t-6962204000-693f70bf6366a395371bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("DG(15:0/18:3(9Z,12Z,15Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000090000-1cbb27a90e650523547bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052t-0099090000-eca62e280c5595793e4dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000n-0099090000-a6866049c39b7067d929View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000090000-70867ade9b27f237daa1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000090000-70867ade9b27f237daa1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ai0-0009000000-c275f36e2b4e95468f57View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000090000-1dffb1eae7d06d9e56e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052t-0088090000-99b936e00e4e72c0c7c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000n-0088090000-e6633f8c1ee15aa1e4fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1166390000-f8d4e3ef3a70c7352587View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08g0-4292010000-5f27b8fd494dee5b3c67View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08i9-6795000000-6e42aef54995b4594d3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2094080000-c5cc0cdc1ab3e6a35c98View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-2090000000-d11e45bc577845051ee0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00bc-2190000000-eec2760e5a2a689c5e47View 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 IDHMDB0007076
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024270
KNApSAcK IDNot Available
Chemspider ID24765909
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14275371
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(15:0/18:3(9Z,12Z,15Z)/0:0) → Cytidine monophosphate + PE(15:0/18:3(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(15:0/18:3(9Z,12Z,15Z)/0:0) + Eicosanoyl-CoA → TG(15:0/18:3(9Z,12Z,15Z)/20:0)[iso6] + Coenzyme Adetails
DG(15:0/18:3(9Z,12Z,15Z)/0:0) + Gondoyl-CoA → TG(15:0/18:3(9Z,12Z,15Z)/20:1(11Z))[iso6] + Coenzyme Adetails
DG(15:0/18:3(9Z,12Z,15Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(15:0/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(15:0/18:3(9Z,12Z,15Z)/0:0) + Docosanoyl-CoA → TG(15:0/18:3(9Z,12Z,15Z)/22:0) + Coenzyme Adetails
DG(15:0/18:3(9Z,12Z,15Z)/0:0) + Erucoyl-CoA → TG(15:0/18:3(9Z,12Z,15Z)/22:1(13Z)) + Coenzyme Adetails
DG(15:0/18:3(9Z,12Z,15Z)/0:0) + Clupanodonyl CoA → TG(15:0/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))[iso6] + Coenzyme Adetails
DG(15:0/18:3(9Z,12Z,15Z)/0:0) + Tetracosanoyl-CoA → TG(15:0/18:3(9Z,12Z,15Z)/24:0) + Coenzyme Adetails