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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:02:58 UTC
Update Date2019-07-23 05:58:10 UTC
HMDB IDHMDB0012562
Secondary Accession Numbers
  • HMDB12562
Metabolite Identification
Common Name13'-Hydroxy-gamma-tocotrienol
Description13'-hydroxy-r-tocotrienol is a precursor in dehydrogenation to form 13'-carboxy-r-tocotrienol by an unidentified microsomal enzyme(s) probably via an aldehyde intermediate. 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?1563861490
Synonyms
ValueSource
13OHgammaTEHMDB
Chemical FormulaC28H42O3
Average Molecular Weight426.6313
Monoisotopic Molecular Weight426.31339521
IUPAC Name(2S)-2-[(3E,7E,11E)-13-hydroxy-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-6-ol
Traditional Name(2S)-2-[(3E,7E,11E)-13-hydroxy-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-2,7,8-trimethyl-3,4-dihydro-1-benzopyran-6-ol
CAS Registry NumberNot Available
SMILES
C\C(CO)=C/CC\C(C)=C\CC\C(C)=C\CC[C@@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2
InChI Identifier
InChI=1S/C28H42O3/c1-20(12-8-13-22(3)19-29)10-7-11-21(2)14-9-16-28(6)17-15-25-18-26(30)23(4)24(5)27(25)31-28/h10,13-14,18,29-30H,7-9,11-12,15-17,19H2,1-6H3/b20-10+,21-14+,22-13+/t28-/m0/s1
InChI KeyBUWYMGRHXZROTQ-XYSSNJNPSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Long chain fatty alcohol
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Fatty alcohol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Fatty acyl
  • Benzenoid
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00057 g/LALOGPS
logP6.85ALOGPS
logP7.5ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)10.47ChemAxon
pKa (Strongest Basic)-2.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity134.66 m³·mol⁻¹ChemAxon
Polarizability53.53 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01vx-2689400000-f0f45afc9c6b0f3c9b04JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0a4i-1274590000-85d672033253c88fa3fcJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0kdi-0532900000-147e78c3eea17197cdf9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0921000000-c63749dfb46f43958ae6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-1910000000-b2f76881968c5f753b67JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-7a12acca59807953034eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-0714900000-1231ef4fa29f185062d1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002b-3928100000-da0467995e252474cbd0JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029128
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481468
PDB IDNot Available
ChEBI IDNot Available
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.