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 00:02:52 UTC |
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Update Date | 2022-03-07 02:51:26 UTC |
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HMDB ID | HMDB0012557 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 13'-Carboxy-gamma-tocopherol |
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Description | 13'-Carboxy-gamma-tocopherol is a dehydrogenation carboxylate product of 13'-hydroxy-r-tocopherol by an unidentified microsomal enzyme(s) probably via an aldehyde intermediate. r-Tocopherol provides different antioxidant activities in food and in-vitro studies and showed higher activity in trapping lipophilic electrophiles and reactive nitrogen and oxygen species. From the metabolism end product, only that of r-tocopherol (2,7,8-trimethyl-2-(b-carboxyethyl)-6-hydroxychroman), but not that of a-tocopherol, was identified to provide natriuretic activity. Only the r-tocopherol plasma level served as biomarker for cancer and cardiovascular risk. |
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Structure | C[C@H](CCC[C@H](C)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2)CCCC(C)C(O)=O InChI=1S/C28H46O4/c1-19(12-8-14-21(3)27(30)31)10-7-11-20(2)13-9-16-28(6)17-15-24-18-25(29)22(4)23(5)26(24)32-28/h18-21,29H,7-17H2,1-6H3,(H,30,31)/t19-,20+,21?,28-/m1/s1 |
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Synonyms | Value | Source |
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13'-Carboxy-g-tocopherol | Generator | 13'-Carboxy-γ-tocopherol | Generator | (6R,10S)-13-[(2R)-6-Hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6,10-trimethyltridecanoate | HMDB |
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Chemical Formula | C28H46O4 |
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Average Molecular Weight | 446.6624 |
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Monoisotopic Molecular Weight | 446.33960996 |
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IUPAC Name | (6R,10S)-13-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6,10-trimethyltridecanoic acid |
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Traditional Name | (6R,10S)-13-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-1-benzopyran-2-yl]-2,6,10-trimethyltridecanoic acid |
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CAS Registry Number | Not Available |
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SMILES | C[C@H](CCC[C@H](C)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2)CCCC(C)C(O)=O |
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InChI Identifier | InChI=1S/C28H46O4/c1-19(12-8-14-21(3)27(30)31)10-7-11-20(2)13-9-16-28(6)17-15-24-18-25(29)22(4)23(5)26(24)32-28/h18-21,29H,7-17H2,1-6H3,(H,30,31)/t19-,20+,21?,28-/m1/s1 |
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InChI Key | WPZHQZIUOXUCOK-PXUFRVCMSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as tocopherols. These are vitamin E derivatives containing a saturated trimethyltridecyl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocotrienols that contain an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain. |
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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 | Quinone and hydroquinone lipids |
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Direct Parent | Tocopherols |
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Alternative Parents | |
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Substituents | - Tocopherol
- Diterpenoid
- Long-chain fatty acid
- Chromane
- Benzopyran
- 1-benzopyran
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Branched fatty acid
- Methyl-branched fatty acid
- Heterocyclic fatty acid
- Hydroxy fatty acid
- Fatty acyl
- Fatty acid
- Benzenoid
- Oxacycle
- Carboxylic acid derivative
- Carboxylic acid
- Organoheterocyclic compound
- Ether
- Monocarboxylic acid or derivatives
- Organic oxide
- Hydrocarbon derivative
- Organic oxygen compound
- Organooxygen compound
- Carbonyl group
- 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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13'-Carboxy-gamma-tocopherol,1TMS,isomer #1 | CC1=C(O[Si](C)(C)C)C=C2CC[C@@](C)(CCC[C@@H](C)CCC[C@@H](C)CCCC(C)C(=O)O)OC2=C1C | 3273.3 | Semi standard non polar | 33892256 | 13'-Carboxy-gamma-tocopherol,1TMS,isomer #2 | CC1=C(O)C=C2CC[C@@](C)(CCC[C@@H](C)CCC[C@@H](C)CCCC(C)C(=O)O[Si](C)(C)C)OC2=C1C | 3243.5 | Semi standard non polar | 33892256 | 13'-Carboxy-gamma-tocopherol,2TMS,isomer #1 | CC1=C(O[Si](C)(C)C)C=C2CC[C@@](C)(CCC[C@@H](C)CCC[C@@H](C)CCCC(C)C(=O)O[Si](C)(C)C)OC2=C1C | 3212.6 | Semi standard non polar | 33892256 | 13'-Carboxy-gamma-tocopherol,1TBDMS,isomer #1 | CC1=C(O[Si](C)(C)C(C)(C)C)C=C2CC[C@@](C)(CCC[C@@H](C)CCC[C@@H](C)CCCC(C)C(=O)O)OC2=C1C | 3544.1 | Semi standard non polar | 33892256 | 13'-Carboxy-gamma-tocopherol,1TBDMS,isomer #2 | CC1=C(O)C=C2CC[C@@](C)(CCC[C@@H](C)CCC[C@@H](C)CCCC(C)C(=O)O[Si](C)(C)C(C)(C)C)OC2=C1C | 3525.9 | Semi standard non polar | 33892256 | 13'-Carboxy-gamma-tocopherol,2TBDMS,isomer #1 | CC1=C(O[Si](C)(C)C(C)(C)C)C=C2CC[C@@](C)(CCC[C@@H](C)CCC[C@@H](C)CCCC(C)C(=O)O[Si](C)(C)C(C)(C)C)OC2=C1C | 3742.4 | 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 - 13'-Carboxy-gamma-tocopherol GC-MS (Non-derivatized) - 70eV, Positive | splash10-000x-2396300000-1dd473dc02ea4da18972 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 13'-Carboxy-gamma-tocopherol GC-MS (2 TMS) - 70eV, Positive | splash10-004i-2167490000-94e2372e73651916e47e | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 13'-Carboxy-gamma-tocopherol 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 - 13'-Carboxy-gamma-tocopherol 10V, Positive-QTOF | splash10-0ufs-0412900000-63565c5e56d90f943080 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocopherol 20V, Positive-QTOF | splash10-0udi-0911100000-4ffe5ea923b2a30ef492 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocopherol 40V, Positive-QTOF | splash10-0udi-1910000000-29ba2d9e2ab77c9f8873 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocopherol 10V, Negative-QTOF | splash10-0002-0000900000-51d8122a565eb68a3eec | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocopherol 20V, Negative-QTOF | splash10-0002-0502900000-e3e6e354d3bb0c65e49f | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocopherol 40V, Negative-QTOF | splash10-007a-7915200000-83fbd3fa7e65ad5850df | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocopherol 10V, Negative-QTOF | splash10-0002-0000900000-560a373e8cd7a465d30d | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocopherol 20V, Negative-QTOF | splash10-0f6t-2328900000-2634c1da4c560ea61f17 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocopherol 40V, Negative-QTOF | splash10-0076-1809200000-6bc39ab36366dcce3a65 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocopherol 10V, Positive-QTOF | splash10-0zmi-0429300000-22647b146ed6d5e17619 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocopherol 20V, Positive-QTOF | splash10-0frb-3956000000-1defc3696e7a013bbd86 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 13'-Carboxy-gamma-tocopherol 40V, Positive-QTOF | splash10-0005-7920000000-088b17bb8a1e7d4289c2 | 2021-09-25 | Wishart Lab | View Spectrum |
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