You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.

TG(18:0/18:0/20:0) (YMDB15878)

Identification
YMDB IDYMDB15878
NameTG(18:0/18:0/20:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionTG(18:0/18:0/20:0) 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(18:0/18:0/20:0) is made up of one octadecanoyl(R1), one octadecanoyl(R2), and one eicosanoyl(R3).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-Stearoyl-2-stearoyl-3-arachidonyl-glycerol
  • Triacylglycerol
  • Triglyceride
  • TAG(56:0)
  • TAG(18:0/18:0/20:0)
  • Tracylglycerol(18:0/18:0/20:0)
  • TG(56:0)
  • 1-Octadecanoyl-2-octadecanoyl-3-eicosanoyl-glycerol
  • Tracylglycerol(56:0)
  • TG(18:0/18:0/20:0)
CAS numberNot Available
WeightAverage: 919.555
Monoisotopic: 918.861541391
InChI KeyJFGIMQPGGNOOHN-UWGNJQTFSA-N
InChIInChI=1S/C59H114O6/c1-4-7-10-13-16-19-22-25-28-29-32-34-37-40-43-46-49-52-58(61)64-55-56(65-59(62)53-50-47-44-41-38-35-31-27-24-21-18-15-12-9-6-3)54-63-57(60)51-48-45-42-39-36-33-30-26-23-20-17-14-11-8-5-2/h56H,4-55H2,1-3H3/t56-/m0/s1
IUPAC Name(2S)-2,3-bis(octadecanoyloxy)propyl icosanoate
Traditional IUPAC Name(2S)-2,3-bis(octadecanoyloxy)propyl icosanoate
Chemical FormulaC59H114O6
SMILES[H][C@](COC(=O)CCCCCCCCCCCCCCCCC)(COC(=O)CCCCCCCCCCCCCCCCCCC)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 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
logP10.68ALOGPS
logP22.48ChemAxon
logS-7.9ALOGPS
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.9 ŲChemAxon
Rotatable Bond Count58ChemAxon
Refractivity278.1 m³·mol⁻¹ChemAxon
Polarizability126.33 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Triacylglycerol metabolism TG(18:0/18:0/20:0)PW007880 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
long-chain fatty acyl-CoA + DG(18:0/20:0/0:0) → Coenzyme A + TG(18:0/18:0/20:0)
TG(18:0/18:0/20:0) + water → hydron + Fatty Acid + DG(18:0/20:0/0:0)
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03do-0000009000-4e9a2fd6de20240d1465JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02u3-0093002001-524cd65140dca973ed95JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02ai-0095001000-3a07807cf1011b371431JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02al-2093000000-3463608937c68613b742JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-5130003109-0de81a2e4cf96c04e1b9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06di-9230001201-93b9e2a9cf0e5c21e67aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06di-6497100100-fc0cf84f2f359066a18fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000000009-6318c3c954b2878c323dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000000009-6318c3c954b2878c323dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0000000009-6318c3c954b2878c323dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000009-d5436771aefd9ce48bb2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000000009-d5436771aefd9ce48bb2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05n0-0010009003-004c0855dca4d42ca809JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0159-0045006009-e794c50823419b1f34c8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08gi-0039002000-0b006d065b329993b590JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06si-2098003000-89d866985090c46e4b4bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000009-8b6e3ec12cecf7aa7febJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000000009-8b6e3ec12cecf7aa7febJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0196-0009009009-96edbad34e224005fd98JSpectraViewer
References
References:
  • Rattray JB, Schibeci A, Kidby DK. (1975). "Lipids of yeasts." Bacteriol Rev. 1975 Sep;39(3):197-231.240350
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB0005394
Pubchem Compound ID131750361
Kegg IDNot Available
ChemSpider IDNot Available
FOODB IDFDB094719
Wikipedia IDNot Available
BioCyc IDNot Available

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.