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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:02:58 UTC
Update Date2022-03-07 02:51:26 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?1582753065
Synonyms
ValueSource
13'-Hydroxy-g-tocotrienolGenerator
13'-Hydroxy-γ-tocotrienolGenerator
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
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
  • 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
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+204.18631661259
DarkChem[M-H]-196.99631661259
DeepCCS[M+H]+219.98930932474
DeepCCS[M-H]-217.59330932474
DeepCCS[M-2H]-250.47730932474
DeepCCS[M+Na]+225.90130932474
AllCCS[M+H]+214.832859911
AllCCS[M+H-H2O]+212.632859911
AllCCS[M+NH4]+216.932859911
AllCCS[M+Na]+217.532859911
AllCCS[M-H]-207.532859911
AllCCS[M+Na-2H]-209.332859911
AllCCS[M+HCOO]-211.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
13'-Hydroxy-gamma-tocotrienolC\C(CO)=C/CC\C(C)=C\CC\C(C)=C\CC[C@@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C24111.2Standard polar33892256
13'-Hydroxy-gamma-tocotrienolC\C(CO)=C/CC\C(C)=C\CC\C(C)=C\CC[C@@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C23341.2Standard non polar33892256
13'-Hydroxy-gamma-tocotrienolC\C(CO)=C/CC\C(C)=C\CC\C(C)=C\CC[C@@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C23513.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
13'-Hydroxy-gamma-tocotrienol,1TMS,isomer #1C/C(=C\CC/C(C)=C/CC[C@@]1(C)CCC2=CC(O)=C(C)C(C)=C2O1)CC/C=C(\C)CO[Si](C)(C)C3282.6Semi standard non polar33892256
13'-Hydroxy-gamma-tocotrienol,1TMS,isomer #2C/C(=C\CC/C(C)=C/CC/C(C)=C/CC[C@@]1(C)CCC2=CC(O[Si](C)(C)C)=C(C)C(C)=C2O1)CO3281.1Semi standard non polar33892256
13'-Hydroxy-gamma-tocotrienol,2TMS,isomer #1C/C(=C\CC/C(C)=C/CC[C@@]1(C)CCC2=CC(O[Si](C)(C)C)=C(C)C(C)=C2O1)CC/C=C(\C)CO[Si](C)(C)C3245.3Semi standard non polar33892256
13'-Hydroxy-gamma-tocotrienol,1TBDMS,isomer #1C/C(=C\CC/C(C)=C/CC[C@@]1(C)CCC2=CC(O)=C(C)C(C)=C2O1)CC/C=C(\C)CO[Si](C)(C)C(C)(C)C3525.9Semi standard non polar33892256
13'-Hydroxy-gamma-tocotrienol,1TBDMS,isomer #2C/C(=C\CC/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)=C2O1)CO3519.2Semi standard non polar33892256
13'-Hydroxy-gamma-tocotrienol,2TBDMS,isomer #1C/C(=C\CC/C(C)=C/CC[C@@]1(C)CCC2=CC(O[Si](C)(C)C(C)(C)C)=C(C)C(C)=C2O1)CC/C=C(\C)CO[Si](C)(C)C(C)(C)C3726.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 13'-Hydroxy-gamma-tocotrienol GC-MS (Non-derivatized) - 70eV, Positivesplash10-01vx-2689400000-f0f45afc9c6b0f3c9b042017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 13'-Hydroxy-gamma-tocotrienol GC-MS (2 TMS) - 70eV, Positivesplash10-0a4i-1274590000-85d672033253c88fa3fc2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 13'-Hydroxy-gamma-tocotrienol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocotrienol 10V, Positive-QTOFsplash10-0kdi-0532900000-147e78c3eea17197cdf92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocotrienol 20V, Positive-QTOFsplash10-0udi-0921000000-c63749dfb46f43958ae62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocotrienol 40V, Positive-QTOFsplash10-0udi-1910000000-b2f76881968c5f753b672017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocotrienol 10V, Negative-QTOFsplash10-004i-0000900000-7a12acca59807953034e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocotrienol 20V, Negative-QTOFsplash10-002b-0714900000-1231ef4fa29f185062d12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocotrienol 40V, Negative-QTOFsplash10-002b-3928100000-da0467995e252474cbd02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocotrienol 10V, Positive-QTOFsplash10-056s-1496600000-aa6abdb3e7525a5733992021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocotrienol 20V, Positive-QTOFsplash10-0002-2693000000-21881151d86350524d152021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocotrienol 40V, Positive-QTOFsplash10-0006-4910000000-d515ae4ba205803ea8892021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocotrienol 10V, Negative-QTOFsplash10-0a4i-0106900000-ef2f1c1214df1d834d4b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocotrienol 20V, Negative-QTOFsplash10-002b-0409200000-e34b7a2a93bb647031902021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Hydroxy-gamma-tocotrienol 40V, Negative-QTOFsplash10-00b9-1719000000-76f0b5cdf15492e1c3392021-09-24Wishart LabView Spectrum
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
FooDB IDFDB029128
KNApSAcK IDNot Available
Chemspider ID30776636
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481468
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDCE7074
MarkerDB IDNot Available
Good Scents 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.