Showing metabocard for TG(16:0/16:0/16:0)[iso] (BMDB0005356)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:15:38 UTC
Update Date2020-05-21 16:27:36 UTC
BMDB IDBMDB0005356
Secondary Accession Numbers
  • BMDB05356
Metabolite Identification
Common NameTG(16:0/16:0/16:0)[iso]
DescriptionTG(16:0/16:0/16:0), also known as tripalmitoylglycerol or glyceryl tripalmitate, 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(16:0/16:0/16:0) is considered to be a triradylglycerol lipid molecule. TG(16:0/16:0/16:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. TG(16:0/16:0/16:0) exists in all eukaryotes, ranging from yeast to humans. In cattle, TG(16:0/16:0/16:0) is involved in the metabolic pathway called the glycerolipid metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2,3-Propanetriol trihexadecanoateChEBI
1,2,3-Propanetriyl trihexadecanoateChEBI
1,2,3-TrihexadecanoylglycerolChEBI
Glycerin tripalmitateChEBI
Glycerol tripalmitateChEBI
Glyceryl trihexadecanoateChEBI
Glyceryl tripalmitateChEBI
Hexadecanoic acid, 1,2,3-propanetriyl esterChEBI
Palmitic acid triglycerin esterChEBI
Palmitic triglycerideChEBI
TG 16:0/16:0/16:0ChEBI
Triglyceryl palmitateChEBI
TrihexadecanoylglycerolChEBI
TripalmitoylglycerolChEBI
1,2,3-Propanetriol trihexadecanoic acidGenerator
1,2,3-Propanetriyl trihexadecanoic acidGenerator
Glycerin tripalmitic acidGenerator
Glycerol tripalmitic acidGenerator
Glyceryl trihexadecanoic acidGenerator
Glyceryl tripalmitic acidGenerator
Hexadecanoate, 1,2,3-propanetriyl esterGenerator
Palmitate triglycerin esterGenerator
Triglyceryl palmitic acidGenerator
1,2,3-Trihexadecanoyl-sn-glycerolHMDB
Barolub LCDHMDB
Dynasan 116HMDB
Dynosan 114HMDB
Spezialfett 116HMDB
Triglyceride PPPHMDB
TripalmitateHMDB
TripalmitinHMDB
Tripalmitoyl glycerolHMDB
Glycero-tripalmitateHMDB
TripalmitylglycerolHMDB
1-Palmitoyl-2-palmitoyl-3-palmitoyl-glycerolHMDB
TG(48:0)HMDB
TriglycerideHMDB
Tracylglycerol(48:0)HMDB
TAG(16:0/16:0/16:0)HMDB
Tracylglycerol(16:0/16:0/16:0)HMDB
TAG(48:0)HMDB
1-Hexadecanoyl-2-hexadecanoyl-3-hexadecanoyl-glycerolHMDB
TriacylglycerolHMDB
TG(16:0/16:0/16:0)Lipid Annotator, ChEBI
Chemical FormulaC51H98O6
Average Molecular Weight807.3202
Monoisotopic Molecular Weight806.736340868
IUPAC Name1,3-bis(hexadecanoyloxy)propan-2-yl hexadecanoate
Traditional Nametripalmitin
CAS Registry Number555-44-2
SMILES
[H]C(COC(=O)CCCCCCCCCCCCCCC)(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C51H98O6/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/h48H,4-47H2,1-3H3
InChI KeyPVNIQBQSYATKKL-UHFFFAOYSA-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 but not 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
logP10.59ALOGPS
logP18.92ChemAxon
logS-7.8ALOGPS
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.9 ŲChemAxon
Rotatable Bond Count50ChemAxon
Refractivity241.29 m³·mol⁻¹ChemAxon
Polarizability109.39 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udr-4266090000-d72def42ee8b15e7d8abView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-5255090000-f2b69e4c01f94e964a8eView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udr-4266090000-d72def42ee8b15e7d8abView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-5255090000-f2b69e4c01f94e964a8eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0udr-4266090000-d72def42ee8b15e7d8abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0udi-5255090000-08a84d0a82ce5839332eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (ACQUITY UPLC System, Waters) 30V, Positivesplash10-0udi-0000090000-b971f7be0932cc17d4fcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (ACQUITY UPLC System, Waters) 30V, Positivesplash10-0udi-0000090000-ba2f475d5deb56cbcb0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000000090-2dcd9d1c90fb060e2d76View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000000090-2dcd9d1c90fb060e2d76View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-0000090070-5e4488c43f4273c179ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0070080190-e59a843e2ac9eb401541View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-053r-0090020000-1e6cc9453781ea6f2f0eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-1090010000-52dbd7332c4689b8becbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000090-497b97a123d4ddbee56bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000090-497b97a123d4ddbee56bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fr-0090090090-3d1ee4df7694f2a67b63View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000090-feacb9716f0cce2e39b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000000090-feacb9716f0cce2e39b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0000000090-feacb9716f0cce2e39b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000000090-c9b5cf0ac5a5011ec584View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000000090-c9b5cf0ac5a5011ec584View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-0010090070-13293a79e092976cb1e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-4130052390-48f5c7a747823dfa0644View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-059i-9150123400-dde2539447879b15fbf1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-4496013000-d20d940fe1d4244aa3e7View in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Membrane
Biospecimen Locations
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
HMDB IDHMDB0005356
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002911
KNApSAcK IDNot Available
Chemspider ID10674
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID3857
PubChem Compound11147
PDB IDNot Available
ChEBI ID77393
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3. [PubMed:1779072 ]

Enzymes

Enzyme Details
1. Hepatic triacylglycerol lipase
General function:
Involved in heparin binding
Specific function:
Hepatic lipase has the capacity to catalyze hydrolysis of phospholipids, mono-, di-, and triglycerides, and acyl-CoA thioesters. It is an important enzyme in HDL metabolism. Hepatic lipase binds heparin (By similarity).
Gene Name:
LIPC
Uniprot ID:
Q3SZ79
Molecular weight:
56826.0
Reactions
TG(16:0/16:0/16:0)[iso] + Water → DG(16:0/16:0/0:0) + Palmitic aciddetails
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(16:0/16:0/0:0) + Palmityl-CoA → TG(16:0/16:0/16:0)[iso] + Coenzyme Adetails