Showing metabocard for DG(16:1(9Z)/16:1(9Z)/0:0) (BMDB0007128)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:31:08 UTC
Update Date2020-06-04 19:52:09 UTC
BMDB IDBMDB0007128
Secondary Accession Numbers
  • BMDB07128
Metabolite Identification
Common NameDG(16:1(9Z)/16:1(9Z)/0:0)
DescriptionDG(16:1(9Z)/16:1(9Z)/0:0), also known as diacylglycerol or DAG(16:1/16:1), belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2. Thus, DG(16:1(9Z)/16:1(9Z)/0:0) is considered to be a diradylglycerol lipid molecule. DG(16:1(9Z)/16:1(9Z)/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(16:1(9Z)/16:1(9Z)/0:0) exists in all living organisms, ranging from bacteria to humans. DG(16:1(9Z)/16:1(9Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, CDP-Ethanolamine and DG(16:1(9Z)/16:1(9Z)/0:0) can be converted into cytidine monophosphate and PE(16:1(9Z)/16:1(9Z)); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. In addition, CDP-Choline and DG(16:1(9Z)/16:1(9Z)/0:0) can be converted into cytidine monophosphate and PC(16:1(9Z)/16:1(9Z)) through the action of the enzyme choline/ethanolaminephosphotransferase. In cattle, DG(16:1(9Z)/16:1(9Z)/0:0) is involved in the metabolic pathway called phosphatidylcholine biosynthesis PC(16:1(9Z)/16:1(9Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2-Di-(9Z-hexadecenoyl)-sn-glycerolHMDB
DAG(16:1/16:1)HMDB
DAG(16:1N7/16:1N7)HMDB
DAG(32:2)HMDB
DG(16:1/16:1/0:0)HMDB
DG(16:1W7/16:1W7)HMDB
DG(32:2)HMDB
1,2-Dipalmitoleoyl-rac-glycerolHMDB
DiglycerideHMDB
DG(16:1/16:1)HMDB
DiacylglycerolHMDB
Diacylglycerol(16:1/16:1)HMDB
1,2-Di(9Z-hexadecenoyl)-rac-glycerolHMDB
Diacylglycerol(32:2)HMDB
DG(16:1(9Z)/16:1(9Z)/0:0)Lipid Annotator
Chemical FormulaC35H64O5
Average Molecular Weight564.8797
Monoisotopic Molecular Weight564.475375158
IUPAC Name(2S)-1-[(9Z)-hexadec-9-enoyloxy]-3-hydroxypropan-2-yl (9Z)-hexadec-9-enoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCC\C=C/CCCCCC
InChI Identifier
InChI=1S/C35H64O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(37)39-32-33(31-36)40-35(38)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13-16,33,36H,3-12,17-32H2,1-2H3/b15-13-,16-14-/t33-/m0/s1
InChI KeyHSQHRRHRYJNSOC-DWCRPSDDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerolipids
Sub ClassDiradylglycerols
Direct Parent1,2-diacylglycerols
Alternative Parents
Substituents
  • 1,2-acyl-sn-glycerol
  • Fatty acid ester
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • 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
logP9.63ALOGPS
logP11.28ChemAxon
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
Refractivity169.93 m³·mol⁻¹ChemAxon
Polarizability72.16 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, Positivesplash10-008i-4449464000-50b6a5cf704160fba39dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("DG(16:1(9Z)/16:1(9Z)/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, Positivesplash10-001i-0000090000-51d305f10f90afe4eb07View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-0009090000-367853de731f7e261d22View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03e9-0009090000-736308809e6d3cc751f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0043090000-9be462094b27393e9285View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0w2i-2092000000-a9d9a5b97c3b76b05af0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-1290000000-987ad4e1a1321117b546View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-2244390000-c5ba870493b35853231dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-7294120000-5fb9d214e1f99e650a8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06rj-9363000000-500eddc99602756cec87View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000090000-279f8e7a1315590373dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-0008090000-54ee6ee0a058250d5412View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03e9-0008090000-cd2f6f1c784cfcb067d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000090000-ec1b73afc18d0387d07fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000090000-ec1b73afc18d0387d07fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0019010000-2a8ef0425a75fbd6ee6cView 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
  • Membrane
Biospecimen Locations
  • All Tissues
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected and Quantified2.90 +/- 0.11 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified4.0 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified5.8 +/- 0.2 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.83 +/- 0.02 uMNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0007128
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 Compound9543679
PDB IDNot Available
ChEBI ID84417
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

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(16:1(9Z)/16:1(9Z)/0:0) → Cytidine monophosphate + PE(16:1(9Z)/16:1(9Z))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(16:1(9Z)/16:1(9Z)/0:0) + Palmitoleyl CoA → TG(16:1(9Z)/16:1(9Z)/16:1(9Z))[iso] + Coenzyme Adetails
DG(16:1(9Z)/16:1(9Z)/0:0) + Stearoyl-CoA → TG(16:1(9Z)/16:1(9Z)/18:0) + Coenzyme Adetails
DG(16:1(9Z)/16:1(9Z)/0:0) + Oleoyl-CoA → TG(16:1(9Z)/16:1(9Z)/18:1(9Z)) + Coenzyme Adetails
DG(16:1(9Z)/16:1(9Z)/0:0) + Gamma-linolenoyl-CoA → TG(16:1(9Z)/16:1(9Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(16:1(9Z)/16:1(9Z)/0:0) + Eicosanoyl-CoA → TG(16:1(9Z)/16:1(9Z)/20:0) + Coenzyme Adetails
DG(16:1(9Z)/16:1(9Z)/0:0) + Gondoyl-CoA → TG(16:1(9Z)/16:1(9Z)/20:1(11Z)) + Coenzyme Adetails
DG(16:1(9Z)/16:1(9Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(16:1(9Z)/16:1(9Z)/0:0) + Docosanoyl-CoA → TG(16:1(9Z)/16:1(9Z)/22:0)[iso3] + Coenzyme Adetails
DG(16:1(9Z)/16:1(9Z)/0:0) + Erucoyl-CoA → TG(16:1(9Z)/16:1(9Z)/22:1(13Z))[iso3] + Coenzyme Adetails
DG(16:1(9Z)/16:1(9Z)/0:0) + Clupanodonyl CoA → TG(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails