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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2009-07-25 00:10:35 UTC
Update Date2022-03-07 02:51:27 UTC
HMDB IDHMDB0012958
Secondary Accession Numbers
  • HMDB12958
Metabolite Identification
Common Namegamma-Tocotrienol
Descriptiongamma-Tocotrienol, also known as 7,8-dimethyltocotrienol, belongs to the class of organic compounds known as tocotrienols. These are vitamin E derivatives containing an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain attached to the C6 atom of a benzopyran ring system. They differ from tocopherols that contain a saturated trimethyltridecyl chain. Thus, gamma-tocotrienol is considered to be a quinone lipid molecule. gamma-Tocotrienol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. gamma-Tocotrienol targets cancer cells by inhibiting Id1, a key cancer-promoting protein. gamma-Tocotrienol was shown to trigger cell apoptosis and well as anti-proliferation of cancer cells. This mechanism was also observed in separate prostate cancer and melanoma cell line studies.
Structure
Data?1584461508
Synonyms
ValueSource
(2R)-2,7,8-Trimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-olChEBI
g-TocotrienolGenerator
Γ-tocotrienolGenerator
Tocotrienol, gammaHMDB
(2R)-3,4-Dihydro-2,7,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrien-1-yl]-2H-1-benzopyran-6-olHMDB
(R)-gamma-TocotrienolHMDB
(R)-Γ-tocotrienolHMDB
7,8-DimethyltocotrienolHMDB
D-gamma-TocotrienolHMDB
D-Γ-tocotrienolHMDB
Plastochromanol 3HMDB
gamma-TocotrienolHMDB
Chemical FormulaC28H42O2
Average Molecular Weight410.6319
Monoisotopic Molecular Weight410.318480588
IUPAC Name(2R)-2,7,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol
Traditional Namegamma-tocotrienol
CAS Registry Number14101-61-2
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC[C@]1(C)CCC2=CC(O)=C(C)C(C)=C2O1
InChI Identifier
InChI=1S/C28H42O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-19-26(29)23(5)24(6)27(25)30-28/h11,13,15,19,29H,8-10,12,14,16-18H2,1-7H3/b21-13+,22-15+/t28-/m1/s1
InChI KeyOTXNTMVVOOBZCV-WAZJVIJMSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tocotrienols. These are vitamin E derivatives containing an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocopherols that contain a saturated trimethyltridecyl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct ParentTocotrienols
Alternative Parents
Substituents
  • Tocotrienol
  • Diterpenoid
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point530.80 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1.9e-06 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP10.300 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00034 g/LALOGPS
logP7.71ALOGPS
logP8.78ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)10.47ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity132.88 m³·mol⁻¹ChemAxon
Polarizability52.51 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+198.81331661259
DarkChem[M-H]-197.93531661259
DeepCCS[M+H]+204.82930932474
DeepCCS[M-H]-202.47130932474
DeepCCS[M-2H]-236.33430932474
DeepCCS[M+Na]+211.56330932474
AllCCS[M+H]+212.332859911
AllCCS[M+H-H2O]+209.932859911
AllCCS[M+NH4]+214.432859911
AllCCS[M+Na]+215.132859911
AllCCS[M-H]-202.132859911
AllCCS[M+Na-2H]-203.432859911
AllCCS[M+HCOO]-204.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
gamma-TocotrienolCC(C)=CCC\C(C)=C\CC\C(C)=C\CC[C@]1(C)CCC2=CC(O)=C(C)C(C)=C2O13922.2Standard polar33892256
gamma-TocotrienolCC(C)=CCC\C(C)=C\CC\C(C)=C\CC[C@]1(C)CCC2=CC(O)=C(C)C(C)=C2O13116.4Standard non polar33892256
gamma-TocotrienolCC(C)=CCC\C(C)=C\CC\C(C)=C\CC[C@]1(C)CCC2=CC(O)=C(C)C(C)=C2O13220.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
gamma-Tocotrienol,1TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC[C@]1(C)CCC2=CC(O[Si](C)(C)C)=C(C)C(C)=C2O13058.4Semi standard non polar33892256
gamma-Tocotrienol,1TBDMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC[C@]1(C)CCC2=CC(O[Si](C)(C)C(C)(C)C)=C(C)C(C)=C2O13303.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - gamma-Tocotrienol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4m-5689000000-0d7bfe0a60d4ee1a21092017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - gamma-Tocotrienol GC-MS (1 TMS) - 70eV, Positivesplash10-014i-5434900000-88e1ef1d491000736dfa2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - gamma-Tocotrienol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - gamma-Tocotrienol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocotrienol LC-ESI-QTOF , positive-QTOFsplash10-03di-0000900000-9ea294ff4831f39965a62017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Tocotrienol 10V, Positive-QTOFsplash10-0ik9-0952700000-a647628546759321e97f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Tocotrienol 20V, Positive-QTOFsplash10-0udi-0920000000-5f57114e0b44fb382e342017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Tocotrienol 40V, Positive-QTOFsplash10-0udi-3920000000-61a9fdea487cbd6093ef2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Tocotrienol 10V, Negative-QTOFsplash10-0a4i-0100900000-893e3a2bd3a1a3a2f3362017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Tocotrienol 20V, Negative-QTOFsplash10-0a4j-0932800000-da33f54bd082556fef712017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Tocotrienol 40V, Negative-QTOFsplash10-000e-1933000000-4941dbd0b8867df99c572017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Tocotrienol 10V, Positive-QTOFsplash10-08fs-5295600000-7c0dc451a62c5aa801b92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Tocotrienol 20V, Positive-QTOFsplash10-0udj-6893000000-24e47314ac2c35b77a8b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Tocotrienol 40V, Positive-QTOFsplash10-0006-9800000000-741a3827b0fb740c39e92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Tocotrienol 10V, Negative-QTOFsplash10-0a4i-0000900000-01a5cd11479be7bee1be2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Tocotrienol 20V, Negative-QTOFsplash10-052b-0901300000-ffe985ef6c11eebe38f32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Tocotrienol 40V, Negative-QTOFsplash10-004i-1903000000-8f9de8bc5233fa1f04192021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001298
KNApSAcK IDC00035101
Chemspider ID4445514
KEGG Compound IDC14155
BioCyc IDCPD-15838
BiGG IDNot Available
Wikipedia LinkGamma-Tocotrienol
METLIN IDNot Available
PubChem Compound5282349
PDB IDNot Available
ChEBI ID33277
Food Biomarker OntologyNot Available
VMH IDM01938
MarkerDB IDNot Available
Good Scents IDrw1679281
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.