Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2009-07-25 00:08:55 UTC |
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Update Date | 2021-09-14 14:58:52 UTC |
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HMDB ID | HMDB0012869 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 9'-Carboxy-gamma-tocotrienol |
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Description | 9'-carboxy-r-tocotrienol is a dehydrogenation carboxylate product of 9'-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. |
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Structure | C\C(CC\C=C(/C)C(O)=O)=C/CC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2 InChI=1S/C23H32O4/c1-15(8-6-10-16(2)22(25)26)9-7-12-23(5)13-11-19-14-20(24)17(3)18(4)21(19)27-23/h9-10,14,24H,6-8,11-13H2,1-5H3,(H,25,26)/b15-9+,16-10+/t23-/m1/s1 |
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Synonyms | Value | Source |
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9'-Carboxy-g-tocotrienol | Generator | 9'-Carboxy-γ-tocotrienol | Generator | gamma-CDMOenHC | HMDB | (2E,6E)-9-[(2R)-6-Hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6-dimethylnona-2,6-dienoate | Generator |
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Chemical Formula | C23H32O4 |
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Average Molecular Weight | 372.4978 |
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Monoisotopic Molecular Weight | 372.230059512 |
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IUPAC Name | (2E,6E)-9-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6-dimethylnona-2,6-dienoic acid |
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Traditional Name | (2E,6E)-9-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-1-benzopyran-2-yl]-2,6-dimethylnona-2,6-dienoic acid |
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CAS Registry Number | 17-15-2 |
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SMILES | C\C(CC\C=C(/C)C(O)=O)=C/CC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2 |
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InChI Identifier | InChI=1S/C23H32O4/c1-15(8-6-10-16(2)22(25)26)9-7-12-23(5)13-11-19-14-20(24)17(3)18(4)21(19)27-23/h9-10,14,24H,6-8,11-13H2,1-5H3,(H,25,26)/b15-9+,16-10+/t23-/m1/s1 |
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InChI Key | QSRURDPJEKTSFH-ODPFLYRHSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Monoterpenoids |
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Direct Parent | Bicyclic monoterpenoids |
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Alternative Parents | |
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Substituents | - Bicyclic monoterpenoid
- Benzopyran
- Aromatic monoterpenoid
- Chromane
- 1-benzopyran
- Medium-chain fatty acid
- Branched fatty acid
- 1-hydroxy-2-unsubstituted benzenoid
- Heterocyclic fatty acid
- Hydroxy fatty acid
- Alkyl aryl ether
- Methyl-branched fatty acid
- Unsaturated fatty acid
- Fatty acyl
- Benzenoid
- Fatty acid
- Ether
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Oxacycle
- Carboxylic acid derivative
- Organoheterocyclic compound
- Organic oxygen compound
- Carbonyl group
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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9'-Carboxy-gamma-tocotrienol,1TMS,isomer #1 | C/C(=C\CC[C@]1(C)CCC2=CC(O)=C(C)C(C)=C2O1)CC/C=C(\C)C(=O)O[Si](C)(C)C | 2973.4 | Semi standard non polar | 33892256 | 9'-Carboxy-gamma-tocotrienol,1TMS,isomer #2 | C/C(=C\CC[C@]1(C)CCC2=CC(O[Si](C)(C)C)=C(C)C(C)=C2O1)CC/C=C(\C)C(=O)O | 3076.3 | Semi standard non polar | 33892256 | 9'-Carboxy-gamma-tocotrienol,2TMS,isomer #1 | C/C(=C\CC[C@]1(C)CCC2=CC(O[Si](C)(C)C)=C(C)C(C)=C2O1)CC/C=C(\C)C(=O)O[Si](C)(C)C | 2932.0 | Semi standard non polar | 33892256 | 9'-Carboxy-gamma-tocotrienol,1TBDMS,isomer #1 | C/C(=C\CC[C@]1(C)CCC2=CC(O)=C(C)C(C)=C2O1)CC/C=C(\C)C(=O)O[Si](C)(C)C(C)(C)C | 3236.9 | Semi standard non polar | 33892256 | 9'-Carboxy-gamma-tocotrienol,1TBDMS,isomer #2 | 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)C(=O)O | 3330.6 | Semi standard non polar | 33892256 | 9'-Carboxy-gamma-tocotrienol,2TBDMS,isomer #1 | 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)C(=O)O[Si](C)(C)C(C)(C)C | 3453.5 | Semi standard non polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - 9'-Carboxy-gamma-tocotrienol GC-MS (Non-derivatized) - 70eV, Positive | splash10-0adi-5779000000-8d3c6b46692581e2ac62 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 9'-Carboxy-gamma-tocotrienol GC-MS (2 TMS) - 70eV, Positive | splash10-0udj-4159370000-7195e9af8becde263b58 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 9'-Carboxy-gamma-tocotrienol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9'-Carboxy-gamma-tocotrienol 10V, Positive-QTOF | splash10-0kmi-0429000000-dc65a95053c3e11c0e6d | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9'-Carboxy-gamma-tocotrienol 20V, Positive-QTOF | splash10-0udi-0921000000-37b3605bb8a75795fd9f | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9'-Carboxy-gamma-tocotrienol 40V, Positive-QTOF | splash10-0udi-2910000000-9ac0df4beb7e5e769087 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9'-Carboxy-gamma-tocotrienol 10V, Negative-QTOF | splash10-00di-0009000000-7bf528b3c3f60dd35755 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9'-Carboxy-gamma-tocotrienol 20V, Negative-QTOF | splash10-0092-0419000000-8a1b81b5337e6aaf5107 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9'-Carboxy-gamma-tocotrienol 40V, Negative-QTOF | splash10-01ot-4915000000-10e34dd9546dd49c4fa1 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9'-Carboxy-gamma-tocotrienol 10V, Positive-QTOF | splash10-0pbm-0596000000-27f1b5626b2f99d81401 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9'-Carboxy-gamma-tocotrienol 20V, Positive-QTOF | splash10-055f-1490000000-7975e83aea814419d5d6 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9'-Carboxy-gamma-tocotrienol 40V, Positive-QTOF | splash10-00rf-2910000000-08415f638b34c34162f8 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9'-Carboxy-gamma-tocotrienol 10V, Negative-QTOF | splash10-00fr-0009000000-1ba19b7f4d17484699cf | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9'-Carboxy-gamma-tocotrienol 20V, Negative-QTOF | splash10-002b-0369000000-bb57dbc661d9be7d070f | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9'-Carboxy-gamma-tocotrienol 40V, Negative-QTOF | splash10-0229-0953000000-31db70e8eb5dab82835e | 2021-09-23 | Wishart Lab | View Spectrum |
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