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TG(16:0/16:0/18:0) (YMDB01285)

Identification
YMDB IDYMDB01285
NameTG(16:0/16:0/18:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionTG(16:0/16:0/18:0) belongs to the family of triradyglycerols, which are glycerolipids lipids containing a common glycerol backbone to which at least one fatty acyl group is esterified. Their general formula is [R1]OCC(CO[R2])O[R3]. TG(16:0/16:0/18:0) is made up of one hexadecanoyl(R1), one hexadecanoyl(R2), and one octadecanoyl(R3).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-palmitoyl-2-palmitoyl-3-stearoyl-glycerol
  • TAG(16:0/16:0/18:0)
  • TAG(50:0)
  • TG(16:0/16:0/18:0)
  • TG(50:0)
  • Tracylglycerol(16:0/16:0/18:0)
  • Tracylglycerol(50:0)
  • Triacylglycerol
  • triacylglycerols
  • Triglycerid
  • Triglyceride
  • triglycerides
  • Triglyzerid
  • 1-Hexadecanoyl-2-hexadecanoyl-3-octadecanoyl-glycerol
CAS numberNot Available
WeightAverage: 835.393
Monoisotopic: 834.767641004
InChI KeyDQKMNCLZNGAXNX-DPDRHGIRSA-N
InChIInChI=1S/C53H102O6/c1-4-7-10-13-16-19-22-25-26-29-31-34-37-40-43-46-52(55)58-49-50(59-53(56)47-44-41-38-35-32-28-24-21-18-15-12-9-6-3)48-57-51(54)45-42-39-36-33-30-27-23-20-17-14-11-8-5-2/h50H,4-49H2,1-3H3/t50-/m0/s1
IUPAC Name(2S)-2,3-bis(hexadecanoyloxy)propyl octadecanoate
Traditional IUPAC Name(2S)-2,3-bis(hexadecanoyloxy)propyl octadecanoate
Chemical FormulaC53H102O6
SMILES[H][C@](COC(=O)CCCCCCCCCCCCCCC)(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC
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 DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.1e-05 g/LALOGPS
logP10.63ALOGPS
logP19.81ChemAxon
logS-7.9ALOGPS
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.9 ŲChemAxon
Rotatable Bond Count52ChemAxon
Refractivity250.49 m³·mol⁻¹ChemAxon
Polarizability113.45 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Triacylglycerol metabolism TG(16:0/16:0/18:0)PW007782 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycerolipid metabolismec00561 Map00561
SMPDB Reactions
long-chain fatty acyl-CoA + DG(16:0/18:0/0:0) → Coenzyme A + TG(16:0/16:0/18:0)
TG(16:0/16:0/18:0) + water → hydron + Fatty Acid + DG(16:0/18:0/0:0)
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000090-1588421d9f01dd529931JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000000090-1588421d9f01dd529931JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ug0-0000090030-2a5e3cf65f6e0a31d894JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000090-223de51541149b3b0ccdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000000090-223de51541149b3b0ccdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0000000090-223de51541149b3b0ccdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000000090-90be60e04864d07f44ceJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000000090-90be60e04864d07f44ceJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-0090090090-4c40b86d123f23294789JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090060080-cb10e0ef2b47d6bfca59JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0091010000-fb62445a7aee1e0d2c13JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-1090010000-68063fb4cab6158b18f3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-3120040290-49387adbc8f4b9d5ba39JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0abi-9240010410-01fada46f02941741f61JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-5695102100-da86e0ab182f0055cdabJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000090-388332d7b7282853ecb1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000000090-388332d7b7282853ecb1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ug0-0010090030-4ca7598e140037e687bfJSpectraViewer
References
References:
  • Ejsing, C. S., Sampaio, J. L., Surendranath, V., Duchoslav, E., Ekroos, K., Klemm, R. W., Simons, K., Shevchenko, A. (2009). "Global analysis of the yeast lipidome by quantitative shotgun mass spectrometry." Proc Natl Acad Sci U S A 106:2136-2141.19174513
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17855
HMDB IDHMDB05357
Pubchem Compound ID3246953
Kegg IDC00422
ChemSpider ID2497485
FOODB IDFDB093898
WikipediaTriacylglycerol
BioCyc IDTriacylglycerols

Enzymes

Protein Details
1. Diacylglycerol O-acyltransferase 1
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. Required for storage lipid synthesis. May be involved in lipid particle synthesis from the endoplasmic reticulum and ergosterol biosynthesis
Gene Name:
DGA1
Uniprot ID:
Q08650
Molecular weight:
47710.89844
Reactions
Acyl-CoA + 1,2-diacylglycerol → CoA + triacylglycerol.
Protein Details
2. Sterol esterase TGL1
General function:
Involved in lipid metabolic process
Specific function:
Mediates the hydrolysis of steryl esters. Required for mobilization of steryl ester, thereby playing a central role in lipid metabolism. May have weak lipase activity toward triglycerides upon some conditions, however, the relevance of such activity is unclear in vivo
Gene Name:
TGL1
Uniprot ID:
P34163
Molecular weight:
62978.39844
Reactions
A steryl ester + H(2)O → a sterol + a fatty acid.
Protein Details
3. Lipase 2
General function:
Involved in hydrolase activity, acting on ester bonds
Specific function:
Lipolytic activity towards triacylglycerols and diacylglycerols with short-chain fatty acids
Gene Name:
TGL2
Uniprot ID:
P54857
Molecular weight:
37499.89844
Reactions
Triacylglycerol + H(2)O → diacylglycerol + a carboxylate.
Protein Details
4. Lipase 3
General function:
Involved in metabolic process
Specific function:
Releases specific fatty acids from neutral lipid triacylglycerols (TAG) thereby supplying fatty acids to a general acylation process
Gene Name:
TGL3
Uniprot ID:
P40308
Molecular weight:
73611.79688
Reactions
Triacylglycerol + H(2)O → diacylglycerol + a carboxylate.
Protein Details
5. Lipase 5
General function:
Involved in metabolic process
Specific function:
Releases specific fatty acids from neutral lipid triacylglycerols (TAG) thereby supplying fatty acids to a general acylation process. May have a specific role in sporulation
Gene Name:
TGL5
Uniprot ID:
Q12043
Molecular weight:
84715.10156
Reactions
Triacylglycerol + H(2)O → diacylglycerol + a carboxylate.
Protein Details
6. Lipase 4
General function:
Involved in metabolic process
Specific function:
Releases specific fatty acids from neutral lipid triacylglycerols (TAG) thereby supplying fatty acids to a general acylation process. May have a specific role in sporulation
Gene Name:
TGL4
Uniprot ID:
P36165
Molecular weight:
102716.0
Reactions
Triacylglycerol + H(2)O → diacylglycerol + a carboxylate.