TG(18:1(9Z)/18:1(9Z)/18:1(9Z)) (YMDB01315)

Identification
YMDB IDYMDB01315
NameTG(18:1(9Z)/18:1(9Z)/18:1(9Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionTG(18:1(9Z)/18:1(9Z)/18:1(9Z)) is a trioleic 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(18:1(9Z)/18:1(9Z)/18:1(9Z)), in particular, consists of one chain of oleic acid at the C-1 position, one chain of oleic acid at the C-2 position and one chain of oleic 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-oleoyl-2-oleoyl-3-oleoyl-glycerol
  • TAG(18:1/18:1/18:1)
  • TAG(18:1n9/18:1n9/18:1n9)
  • TAG(18:1w9/18:1w9/18:1w9)
  • TAG(54:3)
  • TG(18:1/18:1/18:1)
  • TG(18:1n9/18:1n9/18:1n9)
  • TG(18:1w9/18:1w9/18:1w9)
  • TG(54:3)
  • Tracylglycerol(18:1/18:1/18:1)
  • Tracylglycerol(18:1n9/18:1n9/18:1n9)
  • Tracylglycerol(18:1w9/18:1w9/18:1w9)
  • Tracylglycerol(54:3)
  • Triacylglycerol
  • Triglyceride
  • (Z)-9-Octadecenoic acid, 1,2,3-propanetriyl ester
  • 1,2,3-Tri-(9Z-octadecenoyl)-glycerol
  • Glycerin trioleate
  • Glycerol trioleate
  • Glycerol triolein
  • Glycerol, tri(cis-9-octadecenoate)
  • Glyceryl trioleate
  • Glyceryl-1,2,3-trioleate
  • Oleic acid triglyceride
  • Oleic triglyceride
  • Olein
  • Oleyl triglyceride
  • Propane-1,2,3-triyl (9Z,9'z,9''z)tris-octadec-9-enoate
  • TG(18:1(9Z)/18:1(9Z)/18:1(9Z))[iso]
  • Trioleoylglyceride
  • Trioleoylglycerol
  • (Z)-9-Octadecenoate, 1,2,3-propanetriyl ester
  • Glycerin trioleic acid
  • Glycerol trioleic acid
  • Glycerol, tri(cis-9-octadecenoic acid)
  • Glyceryl trioleic acid
  • Glyceryl-1,2,3-trioleic acid
  • Oleate triglyceride
  • Propane-1,2,3-triyl (9Z,9'z,9''z)tris-octadec-9-enoic acid
  • Glycerol, trioleyl
  • Trioleate, glycerol
  • Trioleate-glycerin
  • Trielaidin
  • Trioleate glycerin
  • Trioleyl glycerol
  • TG(18:1(9Z)/18:1(9Z)/18:1(9Z))
  • 1-(9Z-octadecenoyl)-2-(9Z-octadecenoyl)-3-(9Z-octadecenoyl)-glycerol
  • Triolein
CAS numberNot Available
WeightAverage: 885.4321
Monoisotopic: 884.78329106
InChI KeyPHYFQTYBJUILEZ-IUPFWZBJSA-N
InChIInChI=1S/C57H104O6/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-46-49-55(58)61-52-54(63-57(60)51-48-45-42-39-36-33-30-27-24-21-18-15-12-9-6-3)53-62-56(59)50-47-44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h25-30,54H,4-24,31-53H2,1-3H3/b28-25-,29-26-,30-27-
IUPAC Name1,3-bis[(9Z)-octadec-9-enoyloxy]propan-2-yl (9Z)-octadec-9-enoate
Traditional IUPAC Nametriolein
Chemical FormulaC57H104O6
SMILES[H]C(COC(=O)CCCCCCC\C=C/CCCCCCCC)(COC(=O)CCCCCCC\C=C/CCCCCCCC)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 Solubility6.1e-06 g/LALOGPS
logP10.82ALOGPS
logP20.51ChemAxon
logS-8.2ALOGPS
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.9 ŲChemAxon
Rotatable Bond Count53ChemAxon
Refractivity272.25 m³·mol⁻¹ChemAxon
Polarizability116.96 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
8500 ± 4825 umol/L SD media with 2% raffinose24 oCBY4741PMID: 19174513
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 30V, positivesplash10-000i-0000000090-91d6e8bb3820a2b9ebdeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 46V, positivesplash10-000i-0025004090-32e831ad9bb94e656965JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 61V, positivesplash10-00kr-4689024020-7527d97fb03536363c5bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 77V, positivesplash10-00lb-6942000000-37f17691e5732c6d232bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 93V, positivesplash10-000t-7920000000-8d53f79404c44a257cbcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 109V, positivesplash10-0532-9800000000-5ddd79d8af2c416bab4dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 123V, positivesplash10-0532-9700000000-e96406e89785ef71e711JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, positivesplash10-0udi-0000019030-5f72f64cb14b99025263JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, positivesplash10-03di-0158960000-bad288273f5f0ef006e8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, positivesplash10-00or-0054190000-2d9cb5e1963a459c8830JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, positivesplash10-0002-3940000000-daf7601cc0abe13d83faJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 31V, positivesplash10-0udi-0000009000-6d75632a4c7e9871410cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 42V, positivesplash10-0uxr-5671009000-a4a6beef3d7f47884d90JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 53V, positivesplash10-015a-9830001000-493c7832f4a4288ca519JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 63V, positivesplash10-00l2-9510000000-48886ae654cd58f8e05dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 74V, positivesplash10-05o1-9400000000-50d3f5f119ff86e93d72JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 84V, positivesplash10-05o1-9300000000-c9f83ff0d877bf07548bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 95V, positivesplash10-067j-9200000000-362946f8ec43e2da1de6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 106V, positivesplash10-067j-9100000000-3cbc32304732b7cd617eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 127V, positivesplash10-067i-9100000000-975bad5ee71e2769d5a6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, positivesplash10-014i-0094041000-972891f073da867b3319JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, positivesplash10-0072-2900000000-23da0caf841c568c5920JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000009-7ebc474373ce1c8c3388JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000000009-7ebc474373ce1c8c3388JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-0000009061-c361cdac983d0cdffd59JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
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 ID53753
HMDB IDHMDB0005453
Pubchem Compound ID5497163
Kegg IDNot Available
ChemSpider ID4593733
FOODB IDFDB094046
Wikipedia IDTriolein
BioCyc IDNot Available