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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:08:33 UTC
Update Date2020-02-26 21:37:54 UTC
HMDB IDHMDB0012851
Secondary Accession Numbers
  • HMDB12851
Metabolite Identification
Common Name7'-Carboxy-gamma-tocotrienol
Description7'-carboxy-r-tocotrienol is a dehydrogenation carboxylate product of 7'-hydroxy-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?1582753074
Synonyms
ValueSource
7'-Carboxy-g-tocotrienolGenerator
7'-Carboxy-γ-tocotrienolGenerator
gamma-CMHenHCHMDB
Γ-cmhenhcHMDB
γ-Carboxymethylhexenyl hydroxychromanHMDB
γ-CarboxymethylhexenylhydroxychromanHMDB
gamma-Carboxymethylhexenyl hydroxychromanHMDB
gamma-CarboxymethylhexenylhydroxychromanHMDB
(4E)-7-[(2R)-6-Hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-4-methylhept-4-enoateGenerator
Chemical FormulaC20H28O4
Average Molecular Weight332.4339
Monoisotopic Molecular Weight332.198759384
IUPAC Name(4E)-7-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-4-methylhept-4-enoic acid
Traditional Name(4E)-7-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-1-benzopyran-2-yl]-4-methylhept-4-enoic acid
CAS Registry Number1221262-26-5
SMILES
C\C(CCC(O)=O)=C/CC[C@]1(C)CCC2=CC(O)=C(C)C(C)=C2O1
InChI Identifier
InChI=1S/C20H28O4/c1-13(7-8-18(22)23)6-5-10-20(4)11-9-16-12-17(21)14(2)15(3)19(16)24-20/h6,12,21H,5,7-11H2,1-4H3,(H,22,23)/b13-6+/t20-/m1/s1
InChI KeyNECINJBBPZOJSN-QARGNGGGSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct Parent1-benzopyrans
Alternative Parents
Substituents
  • 1-benzopyran
  • Medium-chain fatty acid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Branched fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Methyl-branched fatty acid
  • Unsaturated fatty acid
  • Fatty acyl
  • Fatty acid
  • Benzenoid
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

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 Solubility0.005 g/LALOGPS
logP4.47ALOGPS
logP5.03ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)4.59ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity96.15 m³·mol⁻¹ChemAxon
Polarizability38.53 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kf-6793000000-1f4f7e996607646580d8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03ki-9226700000-4ad9ef42d5fed71097e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0539000000-c24b18697e6615eaac51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-1911000000-0757b6d1d9deb8db59daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-5900000000-c32bf0a50ecc39c82f83Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0119000000-dc6e16f6c4bfd399878aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01pt-1749000000-1d14d6e939c0373bc7dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4j-9731000000-5018e8a422c062384d6dSpectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
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 IDFDB029188
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481532
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDCE5848
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Birringer M, Pfluger P, Kluth D, Landes N, Brigelius-Flohe R: Identities and differences in the metabolism of tocotrienols and tocopherols in HepG2 cells. J Nutr. 2002 Oct;132(10):3113-8. [PubMed:12368403 ]
  2. Zhao Y, Lee MJ, Cheung C, Ju JH, Chen YK, Liu B, Hu LQ, Yang CS: Analysis of multiple metabolites of tocopherols and tocotrienols in mice and humans. J Agric Food Chem. 2010 Apr 28;58(8):4844-52. doi: 10.1021/jf904464u. [PubMed:20222730 ]