TG(16:1(9Z)/16:1(9Z)/22:0) (YMDB01302)

Identification
YMDB IDYMDB01302
NameTG(16:1(9Z)/16:1(9Z)/22:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionTG(16:1(9Z)/16:1(9Z)/22:0) 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)/22:0), 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 behenic 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-behenoyl-glycerol
  • TAG(16:1/16:1/22:0)
  • TAG(16:1n7/16:1n7/22:0)
  • TAG(16:1w7/16:1w7/22:0)
  • TAG(54:2)
  • TG(16:1/16:1/22:0)
  • TG(16:1n7/16:1n7/22:0)
  • TG(16:1w7/16:1w7/22:0)
  • TG(54:2)
  • Tracylglycerol(16:1/16:1/22:0)
  • Tracylglycerol(16:1n7/16:1n7/22:0)
  • Tracylglycerol(16:1w7/16:1w7/22:0)
  • Tracylglycerol(54:2)
  • Triacylglycerol
  • Triglyceride
  • TAG(22:0/16:1/16:1)
  • TG(22:0/16:1/16:1)
  • Tracylglycerol(22:0/16:1/16:1)
  • 1-Behenoyl-2-palmitoleoyl-3-palmitoleoyl-glycerol
  • 1-Docosanoyl-2-(9Z-hexadecenoyl)-3-(9Z-hexadecenoyl)-glycerol
  • TG(22:0/16:1(9Z)/16:1(9Z))
CAS numberNot Available
WeightAverage: 887.4479
Monoisotopic: 886.798941124
InChI KeyGOLXXQRKCMOJGT-KXSDLMDJSA-N
InChIInChI=1S/C57H106O6/c1-4-7-10-13-16-19-22-25-26-27-28-29-30-33-35-38-41-44-47-50-56(59)62-53-54(63-57(60)51-48-45-42-39-36-32-24-21-18-15-12-9-6-3)52-61-55(58)49-46-43-40-37-34-31-23-20-17-14-11-8-5-2/h20-21,23-24,54H,4-19,22,25-53H2,1-3H3/b23-20-,24-21-/t54-/m1/s1
IUPAC Name(2S)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propyl docosanoate
Traditional IUPAC Name(2S)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propyl docosanoate
Chemical FormulaC57H106O6
SMILES[H][C@](COC(=O)CCCCCCCCCCCCCCCCCCCCC)(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 Solubility7.7e-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
Polarizability118.96 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 PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
10000 ± 675 umol/L SD media with 2% raffinose24 oCBY4741PMID: 19174513
4000 ± 1900 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, Positivesplash10-0019-0076039060-6e3bdf6b89714c68861eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-007t-0097014330-f7716d6b25123ad6c86eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-007a-0074002930-781ffbf1a93251cc6391JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0098003020-bed69b1fa79ac0bdb5dbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f79-0097001000-e1faf8200e561c459d7eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-2095000000-50cd2459b3cb2fdd67baJSpectraViewer
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, Negativesplash10-000i-0063025090-e8f43486429142bb65f9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-0094001000-08dfe597f21b0ddb722aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kbr-1095001000-b5acf856e102aff832beJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-4121015490-b5fe1696863af3de353eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-059j-9041014820-21b00909e2c7cdd68da4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-2290002000-17c73060cdb992ddc040JSpectraViewer
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, Positivesplash10-001t-0011099061-3fbb8ca2729a4e937b35JSpectraViewer
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, Positivesplash10-0xro-0090099090-5d1b82f34ac584bcaf9fJSpectraViewer
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 IDHMDB0046459
Pubchem Compound ID9544288
Kegg IDNot Available
ChemSpider ID7823238
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available