TG(16:1(9Z)/16:1(9Z)/18:0) (YMDB01299)

Identification
YMDB IDYMDB01299
NameTG(16:1(9Z)/16:1(9Z)/18:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionTG(16:1(9Z)/16:1(9Z)/18:0) 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)/18:0), 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 stearic 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-stearoyl-glycerol
  • TAG(16:1/16:1/18:0)
  • TAG(16:1n7/16:1n7/18:0)
  • TAG(16:1w7/16:1w7/18:0)
  • TAG(50:2)
  • TG(16:1/16:1/18:0)
  • TG(16:1n7/16:1n7/18:0)
  • TG(16:1w7/16:1w7/18:0)
  • TG(50:2)
  • Tracylglycerol(16:1/16:1/18:0)
  • Tracylglycerol(16:1n7/16:1n7/18:0)
  • Tracylglycerol(16:1w7/16:1w7/18:0)
  • Tracylglycerol(50:2)
  • Triacylglycerol
  • triacylglycerols
  • Triglycerid
  • Triglyceride
  • triglycerides
  • Triglyzerid
  • TAG(18:0/16:1/16:1)
  • TG(18:0/16:1/16:1)
  • Tracylglycerol(18:0/16:1/16:1)
  • TG(18:0/16:1(9Z)/16:1(9Z))
  • 1-octadecanoyl-2-(9Z-hexadecenoyl)-3-(9Z-hexadecenoyl)-glycerol
  • 1-stearoyl-2-palmitoleoyl-3-palmitoleoyl-glycerol
CAS numberNot Available
WeightAverage: 831.3416
Monoisotopic: 830.736340868
InChI KeyQEZWFCZNHWUARW-XQCAQTCHSA-N
InChIInChI=1S/C53H98O6/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/h20-21,23-24,50H,4-19,22,25-49H2,1-3H3/b23-20-,24-21-/t50-/m1/s1
IUPAC Name(2S)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propyl octadecanoate
Traditional IUPAC Name(2S)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propyl octadecanoate
Chemical FormulaC53H98O6
SMILES[H][C@](COC(=O)CCCCCCCCCCCCCCCCC)(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 Solubility7.3e-06 g/LALOGPS
logP10.72ALOGPS
logP19.09ChemAxon
logS-8.1ALOGPS
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.9 ŲChemAxon
Rotatable Bond Count50ChemAxon
Refractivity252.73 m³·mol⁻¹ChemAxon
Polarizability110.87 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
273500 ± 8600 umol/L SD media with 2% raffinose24 oCBY4741PMID: 19174513
110500 ± 5750 umol/L SD media with 2% raffinose37 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, Positivesplash10-0002-0000000090-93c3165e66d5b5243c09JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000000090-93c3165e66d5b5243c09JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0032-0000090030-3f459e9a6c8373be2206JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090070070-395d6f35227e2f52674eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-0092010000-201dd6e8901d522225b0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kcr-1091000000-0499cc0f943b61ed0672JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000000090-e912eed63cc2639af7e3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000000090-e912eed63cc2639af7e3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0032-0010090030-7ee831c808f732b5e3a4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000090-eaf1283b223bf1dc361cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000000090-eaf1283b223bf1dc361cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0xt0-0040090040-600a9ad771ad3bb15babJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-3320070490-47866fa07326ecf88b4bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-9430030610-40db40c123f8e00c4470JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059l-2390010000-b3a67a8c6d32d37a6568JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000090-b9fd22a0b4e270d0d856JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000000090-b9fd22a0b4e270d0d856JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0000000090-b9fd22a0b4e270d0d856JSpectraViewer
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 IDHMDB05430
Pubchem Compound ID9544010
Kegg IDC00422
ChemSpider ID7822960
FOODB IDFDB112345
WikipediaTriacylglycerol
BioCyc IDTriacylglycerols