Showing metabocard for DG(16:0/18:2(9Z,12Z)/0:0) (BMDB0007103)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:30:38 UTC
Update Date2020-05-21 16:27:38 UTC
BMDB IDBMDB0007103
Secondary Accession Numbers
  • BMDB07103
Metabolite Identification
Common NameDG(16:0/18:2(9Z,12Z)/0:0)
DescriptionDG(16:0/18:2(9Z,12Z)/0:0)[iso2], also known as dg(16:0/18:2(9z,12z)/0:0)[iso2] or DAG(16:0/18:2), 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(16:0/18:2(9Z,12Z)/0:0)[iso2] is considered to be a diradylglycerol lipid molecule. DG(16:0/18:2(9Z,12Z)/0:0)[iso2] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, DG(16:0/18:2(9Z,12Z)/0:0)[iso2] is involved in the metabolic pathway called phosphatidylcholine biosynthesis PC(16:0/18:2(9Z,12Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycerolChEBI
DAG(16:0/18:2)ChEBI
DAG(16:0/18:2N6)ChEBI
DAG(16:0/18:2OMEGA6)ChEBI
DAG(34:2)ChEBI
DG(16:0/18:2)ChEBI
DG(16:0/18:2/0:0)ChEBI
DG(16:0/18:2N6)ChEBI
DG(16:0/18:2OMEGA6)ChEBI
DG(34:2)ChEBI
Diacylglycerol(16:0/18:2)ChEBI
Diacylglycerol(16:0/18:2n6)ChEBI
Diacylglycerol(16:0/18:2omega6)ChEBI
Diacylglycerol(34:2)ChEBI
1-Palmitoyl-2-linoleoyl-sn-glycerolHMDB
DAG(16:0/18:2W6)HMDB
DG(16:0/18:2W6)HMDB
DiacylglycerolHMDB
Diacylglycerol(16:0/18:2W6)HMDB
DiglycerideHMDB
DAG(16:0/18:2(9Z,12Z)/0:0)HMDB
Diacylglycerol(16:0/18:2(9Z,12Z)/0:0)HMDB
DG(16:0/18:2(9Z,12Z)/0:0)Lipid Annotator, ChEBI
Chemical FormulaC37H68O5
Average Molecular Weight592.9328
Monoisotopic Molecular Weight592.506675286
IUPAC Name(2S)-1-(hexadecanoyloxy)-3-hydroxypropan-2-yl (9Z,12Z)-octadeca-9,12-dienoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C37H68O5/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-37(40)42-35(33-38)34-41-36(39)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h11,13,17-18,35,38H,3-10,12,14-16,19-34H2,1-2H3/b13-11-,18-17-/t35-/m0/s1
InChI KeySVXWJFFKLMLOHO-YAIZGCQRSA-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
logP10ALOGPS
logP12.17ChemAxon
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 Count34ChemAxon
Refractivity179.13 m³·mol⁻¹ChemAxon
Polarizability76.9 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, Positivesplash10-03ds-4492114000-aca6ecd98f70ae608635View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("DG(16:0/18:2(9Z,12Z)/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, Positivesplash10-03di-0000009000-f509faf22d917fb30fd3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03g0-0009030000-a900151cd1f35176cc44View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dr-0009013000-3e5f421bbb44019cebecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-2094080000-0439040dd4ce84469eecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-2091000000-4ab71ebb8116ee877b32View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a70-2190000000-bf9844edafc7854d105fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000009000-9c0b9b803bf5ae3e9b28View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03g0-0009030000-98227925d45ae661c0b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dr-0009013000-21a9695ac35ca8a17a46View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03du-1297280000-552f87fdd423fcd69deeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3592000000-836ce144c669a8030143View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-7895000000-edc7dfc5af642bee9672View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000009000-5799a9dd05585a00daf0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000009000-5799a9dd05585a00daf0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a50-0009000000-fb07468d5faff5171d2fView in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • All Tissues
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0007103
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024297
KNApSAcK IDNot Available
Chemspider ID7822645
KEGG Compound IDC00165
BioCyc IDDIACYLGLYCEROL
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543695
PDB IDNot Available
ChEBI ID82927
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(16:0/18:2(9Z,12Z)/0:0) → Cytidine monophosphate + PE(16:0/18:2(9Z,12Z))details
Enzyme Details
2. Lipin 1
General function:
Not Available
Specific function:
Not Available
Gene Name:
LPIN1
Uniprot ID:
E1BPE8
Molecular weight:
102857.0
Reactions
PA(16:0/18:2(9Z,12Z)) + Water → DG(16:0/18:2(9Z,12Z)/0:0) + Hydrogen phosphatedetails
Enzyme Details
3. 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(16:0/18:2(9Z,12Z)/0:0) + Gamma-linolenoyl-CoA → TG(16:0/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))[iso6] + Coenzyme Adetails
DG(16:0/18:2(9Z,12Z)/0:0) + Eicosanoyl-CoA → TG(16:0/18:2(9Z,12Z)/20:0) + Coenzyme Adetails
DG(16:0/18:2(9Z,12Z)/0:0) + Gondoyl-CoA → TG(16:0/18:2(9Z,12Z)/20:1(11Z)) + Coenzyme Adetails
DG(16:0/18:2(9Z,12Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(16:0/18:2(9Z,12Z)/0:0) + Docosanoyl-CoA → TG(16:0/18:2(9Z,12Z)/22:0) + Coenzyme Adetails
DG(16:0/18:2(9Z,12Z)/0:0) + Erucoyl-CoA → TG(16:0/18:2(9Z,12Z)/22:1(13Z)) + Coenzyme Adetails
DG(16:0/18:2(9Z,12Z)/0:0) + Clupanodonyl CoA → TG(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails
DG(16:0/18:2(9Z,12Z)/0:0) + Tetracosanoyl-CoA → TG(16:0/18:2(9Z,12Z)/24:0) + Coenzyme Adetails