TG(16:1(9Z)/16:1(9Z)/20:0) (YMDB01301)

Identification
YMDB IDYMDB01301
NameTG(16:1(9Z)/16:1(9Z)/20:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionTG(16:1(9Z)/16:1(9Z)/20:0) is a dipalmitoleic acid triglyceride. Triglycerides (TGs or TAGs) are also known as triacylglycerols or triacylglycerides, meaning that they are glycerides in which the glycerol is esterified with three fatty acid groups (i.e. fatty acid trimesters of glycerol). TGs may be divided into three general types with respect to their acyl substituents. They are simple or monoacid if they contain only one type of fatty acid, diacid if they contain two types of fatty acids and triacid if three different acyl groups. Chain lengths of the fatty acids in naturally occurring triglycerides can be of varying lengths and saturations but 16, 18 and 20 carbons are the most common. TG(16:1(9Z)/16:1(9Z)/20:0), in particular, consists of one chain of palmitoleic acid at the C-1 position, one chain of palmitoleic acid at the C-2 position and one chain of arachidic acid at the C-3 position. TGs are the main constituent of vegetable oil and animal fats. They contain more than twice the energy (9 kcal/g) of carbohydrates and proteins. (www.cyberlipid.org, www.wikipedia.org)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-palmitoleoyl-2-palmitoleoyl-3-arachidonyl-glycerol
  • TAG(16:1/16:1/20:0)
  • TAG(16:1n7/16:1n7/20:0)
  • TAG(16:1w7/16:1w7/20:0)
  • TAG(52:2)
  • TG(16:1/16:1/20:0)
  • TG(16:1n7/16:1n7/20:0)
  • TG(16:1w7/16:1w7/20:0)
  • TG(52:2)
  • Tracylglycerol(16:1/16:1/20:0)
  • Tracylglycerol(16:1n7/16:1n7/20:0)
  • Tracylglycerol(16:1w7/16:1w7/20:0)
  • Tracylglycerol(52:2)
  • Triacylglycerol
  • triacylglycerols
  • Triglycerid
  • Triglyceride
  • triglycerides
  • Triglyzerid
  • TG(20:0/16:1(9Z)/16:1(9Z))
  • Tracylglycerol(20:0/16:1/16:1)
  • 1-arachidonyl-2-palmitoleoyl-3-palmitoleoyl-glycerol
  • TG(20:0/16:1/16:1)
  • 1-eicosanoyl-2-(9Z-hexadecenoyl)-3-(9Z-hexadecenoyl)-glycerol
  • TAG(20:0/16:1/16:1)
CAS numberNot Available
WeightAverage: 859.3948
Monoisotopic: 858.767640996
InChI KeyKKJVTOLWRSMFEP-RLVGKUCASA-N
InChIInChI=1S/C55H102O6/c1-4-7-10-13-16-19-22-25-26-27-28-31-33-36-39-42-45-48-54(57)60-51-52(61-55(58)49-46-43-40-37-34-30-24-21-18-15-12-9-6-3)50-59-53(56)47-44-41-38-35-32-29-23-20-17-14-11-8-5-2/h20-21,23-24,52H,4-19,22,25-51H2,1-3H3/b23-20-,24-21-/t52-/m1/s1
IUPAC Name(2S)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propyl icosanoate
Traditional IUPAC Name(2S)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propyl icosanoate
Chemical FormulaC55H102O6
SMILES[H][C@](COC(=O)CCCCCCCCCCCCCCCCCCC)(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 Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility7.6e-06 g/LALOGPS
logP10.74ALOGPS
logP19.98ChemAxon
logS-8ALOGPS
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.9 ŲChemAxon
Rotatable Bond Count52ChemAxon
Refractivity261.93 m³·mol⁻¹ChemAxon
Polarizability115.12 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 PathwaysNot Available
KEGG Pathways
Glycerolipid metabolismec00561 Map00561
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
4750 ± 100 umol/L SD media with 2% raffinose24 oCBY4741PMID: 19174513
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000090-2cd5fc1386d560f964faJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000000090-2cd5fc1386d560f964faJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-0000099070-a1d05060075d4b47dc41JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-5230015490-cfe30d512139167ff666JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05g0-9140012820-83af08e55a3ca6d526c2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-007c-3490001000-eeb1fce7b7fcc2c4e483JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000000090-d19de471e852da520bd5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000000090-d19de471e852da520bd5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0j4i-0090099090-911d80dde7b28f49cad2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000090-8124134fd02fc15952b3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000000090-8124134fd02fc15952b3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0000000090-8124134fd02fc15952b3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-0073034090-35afe15766a3811f7c57JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003u-0094001000-cf040887477c4d652cb7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0r2c-1094000000-dc02402b8101258c4a60JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000090-737f74f071afb11b73a8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000000090-737f74f071afb11b73a8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-0030099070-b02faca68dda42a059ccJSpectraViewer
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 IDHMDB05431
Pubchem Compound ID9544078
Kegg IDC00422
ChemSpider ID7823028
FOODB IDFDB112348
WikipediaTriacylglycerol
BioCyc IDTriacylglycerols