Showing metabocard for TG(16:1(9Z)/16:1(9Z)/16:1(9Z))[iso] (BMDB0005432)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:17:08 UTC
Update Date2020-06-04 20:29:25 UTC
BMDB IDBMDB0005432
Secondary Accession Numbers
  • BMDB05432
Metabolite Identification
Common NameTG(16:1(9Z)/16:1(9Z)/16:1(9Z))[iso]
DescriptionTG(16:1(9Z)/16:1(9Z)/16:1(9Z)), also known as TG or 1,2,3-tri-(9Z)-hexadecenoylglycerol, belongs to the class of organic compounds known as triacylglycerols. These are glycerides consisting of three fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Thus, TG(16:1(9Z)/16:1(9Z)/16:1(9Z)) is considered to be a triradylglycerol lipid molecule. TG(16:1(9Z)/16:1(9Z)/16:1(9Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. TG(16:1(9Z)/16:1(9Z)/16:1(9Z)) exists in all eukaryotes, ranging from yeast to humans. In cattle, TG(16:1(9Z)/16:1(9Z)/16:1(9Z)) is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(16:1(9Z)/16:1(9Z)/16:1(9Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2,3-Tri-(9Z)-hexadecenoylglycerolChEBI
1,2,3-Tri-(9Z-hexadecenoyl)glycerolChEBI
Palmitoleoyl triglycerideChEBI
TGChEBI
TG(16:1/16:1/16:1)ChEBI
TripalmitoleoinChEBI
TriacylglycerolLipid Annotator, HMDB
Tracylglycerol(16:1/16:1/16:1)Lipid Annotator, HMDB
TriglycerideLipid Annotator, HMDB
TG(16:1(9Z)/16:1(9Z)/16:1(9Z))Lipid Annotator, ChEBI
Tracylglycerol(48:3)Lipid Annotator, HMDB
TAG(16:1/16:1/16:1)Lipid Annotator, HMDB
TAG(48:3)Lipid Annotator, HMDB
1-palmitoleoyl-2-palmitoleoyl-3-palmitoleoyl-glycerolLipid Annotator, HMDB
1-(9Z-hexadecenoyl)-2-(9Z-hexadecenoyl)-3-(9Z-hexadecenoyl)-glycerolLipid Annotator, HMDB
TG(48:3)Lipid Annotator, HMDB
1,2,3-Propanetriyl ester hexadecenoateHMDB
1,2,3-Propanetriyl ester hexadecenoic acidHMDB
1,2,3-Tri-(9Z-hexadecenoyl)-sn-glycerolHMDB
Chemical FormulaC51H92O6
Average Molecular Weight801.2726
Monoisotopic Molecular Weight800.689390676
IUPAC Name1,3-bis[(9Z)-hexadec-9-enoyloxy]propan-2-yl (9Z)-hexadec-9-enoate
Traditional Name1,3-bis[(9Z)-hexadec-9-enoyloxy]propan-2-yl (9Z)-hexadec-9-enoate
CAS Registry Number30773-83-2
SMILES
[H]C(COC(=O)CCCCCCC\C=C/CCCCCC)(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCC\C=C/CCCCCC
InChI Identifier
InChI=1S/C51H92O6/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-49(52)55-46-48(57-51(54)45-42-39-36-33-30-27-24-21-18-15-12-9-6-3)47-56-50(53)44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h19-24,48H,4-18,25-47H2,1-3H3/b22-19-,23-20-,24-21-
InChI KeySKGWNZXOCSYJQL-BUTYCLJRSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as triacylglycerols. These are glycerides consisting of three fatty acid chains covalently bonded to a glycerol molecule through ester linkages.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerolipids
Sub ClassTriradylcglycerols
Direct ParentTriacylglycerols
Alternative Parents
Substituents
  • Triacyl-sn-glycerol
  • Tricarboxylic acid or derivatives
  • Fatty acid ester
  • Fatty acyl
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Adiposome
  • 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
logP10.62ALOGPS
logP17.84ChemAxon
logS-8.1ALOGPS
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.9 ŲChemAxon
Rotatable Bond Count47ChemAxon
Refractivity244.64 m³·mol⁻¹ChemAxon
Polarizability104.42 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00sj-9610000000-65f50759ee5ed4366df4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00sj-9610000000-7bc9c835ef084d134585View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000000090-612725bdbcd3cfd85e96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000000090-612725bdbcd3cfd85e96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6t-0000090070-2ded13575a72e625234bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000000090-9145dd70e958cc4d5a40View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000000090-9145dd70e958cc4d5a40View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0000000090-9145dd70e958cc4d5a40View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udj-5140094680-7d26a95012c7a83e282dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-9140022500-a9283a1746dcb7db461bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052u-2390021000-10d55c3db16bc6e7008aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000090-1a2aeef18385fa2f907bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000000090-1a2aeef18385fa2f907bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-17vi-0090090090-ab2a95a2c5338d50d092View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090080800-554f5acc9980621b7628View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f9y-0090010000-060f426ac58ad79ff6dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zi0-1090010000-e1c163c1ae7079df73efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000000090-d28701a31408a8caadacView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000000090-d28701a31408a8caadacView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6t-0010090070-f4fe31f869021574231eView in MoNA
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Membrane
Biospecimen Locations
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected and Quantified76 +/- 4 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified124 +/- 13 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified573 +/- 9 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.6 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0005432
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB112224
KNApSAcK IDNot Available
Chemspider ID7822939
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID4719
PubChem Compound9543989
PDB IDNot Available
ChEBI ID75841
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. 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