TG(14:0/16:1(9Z)/16:1(9Z)) (YMDB01274)

Identification
YMDB IDYMDB01274
NameTG(14:0/16:1(9Z)/16:1(9Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionTG(14:0/16:1(9Z)/16:1(9Z)) 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(14:0/16:1(9Z)/16:1(9Z)) is made up of one tetradecanoyl(R1), one 9Z-hexadecenoyl(R2), and one 9Z-hexadecenoyl(R3).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-myristoyl-2-palmitoleoyl-3-palmitoleoyl-glycerol
  • TAG(14:0/16:1/16:1)
  • TAG(14:0/16:1n7/16:1n7)
  • TAG(14:0/16:1w7/16:1w7)
  • TAG(46:2)
  • TG(14:0/16:1/16:1)
  • TG(14:0/16:1n7/16:1n7)
  • TG(14:0/16:1w7/16:1w7)
  • TG(46:2)
  • Tracylglycerol(14:0/16:1/16:1)
  • Tracylglycerol(14:0/16:1n7/16:1n7)
  • Tracylglycerol(14:0/16:1w7/16:1w7)
  • Tracylglycerol(46:2)
  • Triacylglycerol
  • Triglyceride
  • 1-Tetradecanoyl-2-(9Z-hexadecenoyl)-3-(9Z-hexadecenoyl)-glycerol
  • TG(14:0/16:1(9Z)/16:1(9Z))
CAS numberNot Available
WeightAverage: 775.253
Monoisotopic: 774.673740618
InChI KeyXUEMVUXNOCIHLG-ZTJIGJDTSA-N
InChIInChI=1S/C49H90O6/c1-4-7-10-13-16-19-22-24-27-30-33-36-39-42-48(51)54-45-46(44-53-47(50)41-38-35-32-29-26-21-18-15-12-9-6-3)55-49(52)43-40-37-34-31-28-25-23-20-17-14-11-8-5-2/h19-20,22-23,46H,4-18,21,24-45H2,1-3H3/b22-19-,23-20-/t46-/m0/s1
IUPAC Name(2S)-1-[(9Z)-hexadec-9-enoyloxy]-3-(tetradecanoyloxy)propan-2-yl (9Z)-hexadec-9-enoate
Traditional IUPAC Name(2S)-1-[(9Z)-hexadec-9-enoyloxy]-3-(tetradecanoyloxy)propan-2-yl (9Z)-hexadec-9-enoate
Chemical FormulaC49H90O6
SMILES[H][C@](COC(=O)CCCCCCCCCCCCC)(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCC\C=C/CCCCCC
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 Solubility7.6e-06 g/LALOGPS
logP10.56ALOGPS
logP17.31ChemAxon
logS-8ALOGPS
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.9 ŲChemAxon
Rotatable Bond Count46ChemAxon
Refractivity234.32 m³·mol⁻¹ChemAxon
Polarizability101.32 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(14:0/16:1(9Z)/16:1(9Z))PW007735 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
long-chain fatty acyl-CoA + DG(14:0/16:1(9Z)/0:0) → Coenzyme A + TG(14:0/16:1(9Z)/16:1(9Z))
TG(14:0/16:1(9Z)/16:1(9Z)) + water → hydron + Fatty Acid + DG(14:0/16:1(9Z)/0:0)
KEGG ReactionsNot Available
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
123500 ± 2975 umol/L SD media with 2% raffinose24 oCBY4741PMID: 19174513
Conversion Details Here
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, Positivesplash10-0006-0000000900-ba9310e38a4cbf853f92JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000000900-ba9310e38a4cbf853f92JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ft-0000090300-e70cd3e4d2d40375be5dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090060700-dcf630649414c782728eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00o3-0090010000-94274db014ff16d8669cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kdi-0090010000-c7687058b51cab2e6b65JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000900-b857b03710576755a878JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000000900-b857b03710576755a878JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0xx0-0040090400-cfe9ef9ca7e9f06013a7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-2210053900-1e21f19219787b4e6044JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052s-9150047800-cdd2b0aefc17dbf5b441JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-2290012000-f686120c7b6b191863deJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000000900-2ff637bade4c9155f1dfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000000900-2ff637bade4c9155f1dfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ft-0010090300-55a0b69860807f4bfd08JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000000900-0c02b6c2996339968cb6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000000900-0c02b6c2996339968cb6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0000000900-0c02b6c2996339968cb6JSpectraViewer
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 IDNot Available
HMDB IDHMDB0042309
Pubchem Compound ID131753451
Kegg IDNot Available
ChemSpider IDNot Available
FOODB IDNot Available
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.