TG(16:1(9Z)/18:1(9Z)/20:0) (YMDB01308)

Identification
YMDB IDYMDB01308
NameTG(16:1(9Z)/18:1(9Z)/20:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionTG(16:1(9Z)/18:1(9Z)/20:0) is a monoarachidic 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)/18:1(9Z)/20:0), in particular, consists of one chain of palmitoleic acid at the C-1 position, one chain of oleic 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-oleoyl-3-arachidonyl-glycerol
  • TAG(16:1/18:1/20:0)
  • TAG(16:1n7/18:1n9/20:0)
  • TAG(16:1w7/18:1w9/20:0)
  • TAG(54:2)
  • TG(16:1/18:1/20:0)
  • TG(16:1n7/18:1n9/20:0)
  • TG(16:1w7/18:1w9/20:0)
  • TG(54:2)
  • Tracylglycerol(16:1/18:1/20:0)
  • Tracylglycerol(16:1n7/18:1n9/20:0)
  • Tracylglycerol(16:1w7/18:1w9/20:0)
  • Tracylglycerol(54:2)
  • Triacylglycerol
  • triacylglycerols
  • Triglycerid
  • Triglyceride
  • triglycerides
  • Triglyzerid
  • 1-arachidonyl-2-oleoyl-3-palmitoleoyl-glycerol
  • TG(20:0/18:1(9Z)/16:1(9Z))
  • TAG(20:0/18:1/16:1)
  • Tracylglycerol(20:0/18:1/16:1)
  • 1-eicosanoyl-2-(9Z-octadecenoyl)-3-(9Z-hexadecenoyl)-glycerol
  • TG(20:0/18:1/16:1)
CAS numberNot Available
WeightAverage: 887.4479
Monoisotopic: 886.798941124
InChI KeyINYBBHQUSIBINH-OMJPTUBSSA-N
InChIInChI=1S/C57H106O6/c1-4-7-10-13-16-19-22-25-27-28-30-32-35-38-41-44-47-50-56(59)62-53-54(52-61-55(58)49-46-43-40-37-34-31-24-21-18-15-12-9-6-3)63-57(60)51-48-45-42-39-36-33-29-26-23-20-17-14-11-8-5-2/h21,24,26,29,54H,4-20,22-23,25,27-28,30-53H2,1-3H3/b24-21-,29-26-/t54-/m1/s1
IUPAC Name(2S)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propyl icosanoate
Traditional IUPAC Name(2S)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propyl icosanoate
Chemical FormulaC57H106O6
SMILES[H][C@](COC(=O)CCCCCCCCCCCCCCCCCCC)(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC
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 Solubility7.7e-06 g/LALOGPS
logP10.76ALOGPS
logP20.87ChemAxon
logS-8.1ALOGPS
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.9 ŲChemAxon
Rotatable Bond Count54ChemAxon
Refractivity271.13 m³·mol⁻¹ChemAxon
Polarizability119.25 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
4500 ± 300 umol/L SD media with 2% raffinose24 oCBY4741PMID: 19174513
1750 ± 850 umol/L SD media with 2% raffinose37 oCBY4741PMID: 19174513
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gw3-0092001010-b0a32799ce72534382a1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ik9-0094000000-32c35dbe7b1f445092c8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ikc-2092000000-06e97a180903f9f01364JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0065025090-77cd40f6613432261b16JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-0059001000-e9c2193cfd864b7e49f6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bt9-2079001000-e573b2b939e911b4b161JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0091014030-29b50c50aeeac37c5277JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0092002110-79c50e5e564778d46106JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0091000520-f09fe302c509e1b6af32JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000000090-f5c46038847a5de9a350JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000000090-f5c46038847a5de9a350JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03ec-0090099090-f6288c583077765e3815JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05n0-4270015390-532bfd0551c9bf91efcbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01b9-9380012520-7abd8f6909f301c2596eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bc-3591001000-1a32755ba2d2e6bb2ae0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000009-e6a1831b611ff124b318JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000000009-e6a1831b611ff124b318JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0000000009-e6a1831b611ff124b318JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000009-0f0a8c9c475c5b25cbc2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000000009-0f0a8c9c475c5b25cbc2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aar-0020049030-5cd1a21e93758b5b2493JSpectraViewer
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 IDHMDB05437
Pubchem Compound ID9544196
Kegg IDC00422
ChemSpider ID7823146
FOODB IDFDB112349
WikipediaTriacylglycerol
BioCyc IDTriacylglycerols