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TG(18:0/18:0/18:0) (YMDB01096)

Identification
YMDB IDYMDB01096
NameTG(18:0/18:0/18:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionTG(18:0/18:0/18:0) 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(18:0/18:0/18:0) is made up of one octadecanoyl(R1), one octadecanoyl(R2), and one octadecanoyl(R3).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-stearoyl-2-stearoyl-3-stearoyl-glycerol
  • 1,2,3-Propanetriyl trioctadecanoate
  • 2,3-Bis(stearoyloxy)propyl stearate
  • Glycerol trioctadecanoate
  • Glycerol tristearate
  • Glyceryl tristearate
  • Octadecanoic acid, 1,2,3-propanetriyl ester
  • Stearic acid triglyceride
  • Stearic acid triglycerin ester
  • Stearic triglyceride
  • Stearin
  • Stearin, tri-
  • Stearoyl triglyceride
  • Tracylglycerol(18:0/18:0/18:0)
  • Tracylglycerol(54:0)
  • Triacylglycerol
  • triacylglycerols
  • Triglycerid
  • Triglyceride
  • triglycerides
  • Triglyzerid
  • Trioctadecanoin
  • Tristearin
  • 2,3-Di(octadecanoyloxy)propyl octadecanoate
  • Trioctadecanoylglycerol
  • Tristearoyl-sn-glycerol
  • 2,3-Di(octadecanoyloxy)propyl octadecanoic acid
  • Glyceryl tristearic acid
  • Stearate triglycerin ester
  • Tristearoylglycerol
  • TG(18:0/18:0/18:0)
  • TAG(18:0/18:0/18:0)
  • TAG(54:0)
  • 1-octadecanoyl-2-octadecanoyl-3-octadecanoyl-glycerol
  • TG(54:0)
CAS number555-43-1
WeightAverage: 891.4797
Monoisotopic: 890.830241252
InChI KeyDCXXMTOCNZCJGO-UHFFFAOYSA-N
InChIInChI=1S/C57H110O6/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-46-49-55(58)61-52-54(63-57(60)51-48-45-42-39-36-33-30-27-24-21-18-15-12-9-6-3)53-62-56(59)50-47-44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h54H,4-53H2,1-3H3
IUPAC Name1,3-bis(octadecanoyloxy)propan-2-yl octadecanoate
Traditional IUPAC Namestearin
Chemical FormulaC57H110O6
SMILESCCCCCCCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCC
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
Physical Properties
StateSolid
Charge0
Melting point55 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.1e-05 g/LALOGPS
logP10.68ALOGPS
logP21.59ChemAxon
logS-7.9ALOGPS
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.9 ŲChemAxon
Rotatable Bond Count56ChemAxon
Refractivity268.9 m³·mol⁻¹ChemAxon
Polarizability122.4 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • lipid particle
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Triacylglycerol metabolism TG(18:0/18:0/18:0)PW007843 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycerolipid metabolismec00561 Map00561
SMPDB Reactions
long-chain fatty acyl-CoA + DG(18:0/18:0/0:0) → Coenzyme A + TG(18:0/18:0/18:0)
TG(18:0/18:0/18:0) + water → hydron + Fatty Acid + DG(18:0/18:0/0:0)
KEGG Reactions
acyl-CoA + DG(16:0/16:0/0:0) ↔ hydron + TG(18:0/18:0/18:0) + Coenzyme A
DG(16:0/16:0/0:0) + short-chain fatty acid ↔ TG(18:0/18:0/18:0)
DG(16:0/16:0/0:0) + fatty acid ↔ TG(18:0/18:0/18:0) + water
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0aor-1268019000-bea2c9645ee3c4900166JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0aor-1268019000-bea2c9645ee3c4900166JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0aor-1268019000-bea2c9645ee3c4900166JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0aor-1268019000-bea2c9645ee3c4900166JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000009-2e72f9bb2fcaaf828b27JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000000009-2e72f9bb2fcaaf828b27JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-0000009061-f9334cb97067aff8107cJSpectraViewer
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, Negativesplash10-053i-0043006090-aeaea3ab6b0a4236072aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bu0-0049003010-e3bfb827784335c5edd2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-2095012000-957fb0240d12665dad8eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000000090-79fc8ab666c6e84b1368JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000000090-79fc8ab666c6e84b1368JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dq-0090009090-e13cd3f8ab7c7e9c1b7bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-5120003390-7c67e17e3ae00ed1084fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0avi-9140102310-25b723724b97b6004b57JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-5397211000-3ff6387ac1ed487a7280JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000009-1ad7310063865c7c08aeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000000009-1ad7310063865c7c08aeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-0010009061-4c61e1bfc065714b1855JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000009-b360d413a092fefef62eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000009-b360d413a092fefef62eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0000000009-b360d413a092fefef62eJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
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
  • Yannai S. Dictionary of food compounds with CD-ROM: additives, flavors, and ingredients. Chapman & Hall/CRC; 2004.
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17855
HMDB IDHMDB05393
Pubchem Compound ID11146
Kegg IDC00422
ChemSpider ID10673
FOODB IDFDB002912
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.