Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 23:52:25 UTC |
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Update Date | 2022-03-07 02:55:49 UTC |
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HMDB ID | HMDB0038549 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Toralactone |
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Description | Toralactone belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. Toralactone has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, herbs and spices, pulses, and robusta coffees (Coffea canephora). This could make toralactone a potential biomarker for the consumption of these foods. Toralactone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Toralactone. |
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Structure | COC1=CC(O)=C2C(O)=C3C(=O)OC(C)=CC3=CC2=C1 InChI=1S/C15H12O5/c1-7-3-8-4-9-5-10(19-2)6-11(16)12(9)14(17)13(8)15(18)20-7/h3-6,16-17H,1-2H3 |
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Synonyms | Value | Source |
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9,10-Dihydroxy-7-methoxy-3-methyl-1H-naphtho(2,3-c)pyran-1-one | ChEBI | 9,10-Dihydroxy-7-methoxy-3-methyl-1H-naphtho[2,3-c]pyran-1-one, 9ci | HMDB |
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Chemical Formula | C15H12O5 |
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Average Molecular Weight | 272.2528 |
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Monoisotopic Molecular Weight | 272.068473494 |
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IUPAC Name | 9,10-dihydroxy-7-methoxy-3-methyl-1H-benzo[g]isochromen-1-one |
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Traditional Name | 9,10-dihydroxy-7-methoxy-3-methylbenzo[g]isochromen-1-one |
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CAS Registry Number | 41743-74-2 |
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SMILES | COC1=CC(O)=C2C(O)=C3C(=O)OC(C)=CC3=CC2=C1 |
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InChI Identifier | InChI=1S/C15H12O5/c1-7-3-8-4-9-5-10(19-2)6-11(16)12(9)14(17)13(8)15(18)20-7/h3-6,16-17H,1-2H3 |
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InChI Key | WEHXAEGTVPWKDY-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Naphthopyrans |
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Sub Class | Naphthopyranones |
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Direct Parent | Naphthopyranones |
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Alternative Parents | |
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Substituents | - Naphthopyranone
- Isocoumarin
- 1-naphthol
- Benzopyran
- Naphthalene
- 2-benzopyran
- Anisole
- Alkyl aryl ether
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Pyranone
- Pyran
- Benzenoid
- Heteroaromatic compound
- Vinylogous acid
- Lactone
- Ether
- Oxacycle
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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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 | 252 - 254 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 34.72 mg/L @ 25 °C (est) | The Good Scents Company Information System | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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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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Toralactone,1TMS,isomer #1 | COC1=CC(O[Si](C)(C)C)=C2C(O)=C3C(=O)OC(C)=CC3=CC2=C1 | 2850.2 | Semi standard non polar | 33892256 | Toralactone,1TMS,isomer #2 | COC1=CC(O)=C2C(O[Si](C)(C)C)=C3C(=O)OC(C)=CC3=CC2=C1 | 2843.8 | Semi standard non polar | 33892256 | Toralactone,2TMS,isomer #1 | COC1=CC(O[Si](C)(C)C)=C2C(O[Si](C)(C)C)=C3C(=O)OC(C)=CC3=CC2=C1 | 2925.0 | Semi standard non polar | 33892256 | Toralactone,1TBDMS,isomer #1 | COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(O)=C3C(=O)OC(C)=CC3=CC2=C1 | 3059.4 | Semi standard non polar | 33892256 | Toralactone,1TBDMS,isomer #2 | COC1=CC(O)=C2C(O[Si](C)(C)C(C)(C)C)=C3C(=O)OC(C)=CC3=CC2=C1 | 3053.4 | Semi standard non polar | 33892256 | Toralactone,2TBDMS,isomer #1 | COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(O[Si](C)(C)C(C)(C)C)=C3C(=O)OC(C)=CC3=CC2=C1 | 3324.4 | Semi standard non polar | 33892256 |
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Spectra |
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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 - Toralactone GC-MS (Non-derivatized) - 70eV, Positive | splash10-0abc-0190000000-0b6644937e0069cfba34 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Toralactone GC-MS (2 TMS) - 70eV, Positive | splash10-0uk9-2009400000-28388824cb8fdaf3e748 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Toralactone 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 - Toralactone 10V, Positive-QTOF | splash10-00di-0090000000-af0e4aa15b772877e705 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Toralactone 20V, Positive-QTOF | splash10-00di-0090000000-67a31feccf2de0c2d09c | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Toralactone 40V, Positive-QTOF | splash10-002b-0890000000-b766d9ba09c1aa5c07ac | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Toralactone 10V, Negative-QTOF | splash10-00di-0090000000-a304bd0b8e4313937885 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Toralactone 20V, Negative-QTOF | splash10-00di-0090000000-b199e2cdf9b618446ccb | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Toralactone 40V, Negative-QTOF | splash10-004j-1980000000-284d4a71b00b8c9cc8c5 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Toralactone 10V, Positive-QTOF | splash10-00di-0090000000-031a5312b116bdf1aa4a | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Toralactone 20V, Positive-QTOF | splash10-00di-0090000000-e8cad39c3f9c861b9b61 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Toralactone 40V, Positive-QTOF | splash10-0fi9-0490000000-d32339d75f0f0ea86780 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Toralactone 10V, Negative-QTOF | splash10-00di-0090000000-d6b6f6391b4e9f4522f4 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Toralactone 20V, Negative-QTOF | splash10-00di-0090000000-d6b6f6391b4e9f4522f4 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Toralactone 40V, Negative-QTOF | splash10-00dj-3970000000-0694d792101fade0dd10 | 2021-09-24 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB017935 |
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KNApSAcK ID | C00032364 |
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Chemspider ID | 4479581 |
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KEGG Compound ID | C17673 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 5321980 |
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PDB ID | Not Available |
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ChEBI ID | 78029 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | rw1351071 |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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