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 23:30:27 UTC |
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Update Date | 2022-03-07 02:55:41 UTC |
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HMDB ID | HMDB0038225 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Glycycoumarin |
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Description | Glycycoumarin belongs to the class of organic compounds known as hydroxyisoflavonoids. These are organic compounds containing an isoflavonoid skeleton carrying one or more hydroxyl groups. Thus, glycycoumarin is considered to be a flavonoid. Glycycoumarin has been detected, but not quantified in, root vegetables. This could make glycycoumarin a potential biomarker for the consumption of these foods. Glycycoumarin 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 Glycycoumarin. |
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Structure | COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C(=O)O2)C1=C(O)C=C(O)C=C1 InChI=1S/C21H20O6/c1-11(2)4-6-14-18(24)10-19-16(20(14)26-3)9-15(21(25)27-19)13-7-5-12(22)8-17(13)23/h4-5,7-10,22-24H,6H2,1-3H3 |
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Synonyms | Value | Source |
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3-(2,4-Dihydroxy-phenyl)-7-hydroxy-5-methoxy-6-(3-methyl-but-2-enyl)-1-benzopyran-2-one | ChEBI | 3-(2,4-Dihydroxyphenyl)-7-hydroxy-5-methoxy-6-(3-methyl-2-butenyl)-2H-1-benzopyran-2-one, 9ci | HMDB |
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Chemical Formula | C21H20O6 |
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Average Molecular Weight | 368.3799 |
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Monoisotopic Molecular Weight | 368.125988372 |
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IUPAC Name | 3-(2,4-dihydroxyphenyl)-7-hydroxy-5-methoxy-6-(3-methylbut-2-en-1-yl)-2H-chromen-2-one |
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Traditional Name | glycycoumarin |
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CAS Registry Number | 94805-82-0 |
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SMILES | COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C(=O)O2)C1=C(O)C=C(O)C=C1 |
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InChI Identifier | InChI=1S/C21H20O6/c1-11(2)4-6-14-18(24)10-19-16(20(14)26-3)9-15(21(25)27-19)13-7-5-12(22)8-17(13)23/h4-5,7-10,22-24H,6H2,1-3H3 |
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InChI Key | NZYSZZDSYIBYLC-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as hydroxyisoflavonoids. These are organic compounds containing an isoflavonoid skeleton carrying one or more hydroxyl groups. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Isoflavonoids |
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Sub Class | Hydroxyisoflavonoids |
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Direct Parent | Hydroxyisoflavonoids |
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Alternative Parents | |
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Substituents | - Hydroxyisoflavonoid
- Isoflav-3-enone skeleton
- 7-hydroxycoumarin
- Hydroxycoumarin
- Coumarin
- Benzopyran
- 1-benzopyran
- Anisole
- Resorcinol
- 1-hydroxy-4-unsubstituted benzenoid
- Alkyl aryl ether
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Pyranone
- Monocyclic benzene moiety
- Pyran
- Benzenoid
- Heteroaromatic compound
- Lactone
- Ether
- Oxacycle
- Organoheterocyclic compound
- 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 | 243.5 - 244.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 4.11 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 | |
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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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Glycycoumarin,1TMS,isomer #1 | COC1=C(CC=C(C)C)C(O[Si](C)(C)C)=CC2=C1C=C(C1=CC=C(O)C=C1O)C(=O)O2 | 3294.6 | Semi standard non polar | 33892256 | Glycycoumarin,1TMS,isomer #2 | COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C1=CC=C(O)C=C1O[Si](C)(C)C)C(=O)O2 | 3250.8 | Semi standard non polar | 33892256 | Glycycoumarin,1TMS,isomer #3 | COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C)C=C1O)C(=O)O2 | 3264.5 | Semi standard non polar | 33892256 | Glycycoumarin,2TMS,isomer #1 | COC1=C(CC=C(C)C)C(O[Si](C)(C)C)=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C)C=C1O)C(=O)O2 | 3170.4 | Semi standard non polar | 33892256 | Glycycoumarin,2TMS,isomer #2 | COC1=C(CC=C(C)C)C(O[Si](C)(C)C)=CC2=C1C=C(C1=CC=C(O)C=C1O[Si](C)(C)C)C(=O)O2 | 3170.0 | Semi standard non polar | 33892256 | Glycycoumarin,2TMS,isomer #3 | COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C)C(=O)O2 | 3166.7 | Semi standard non polar | 33892256 | Glycycoumarin,3TMS,isomer #1 | COC1=C(CC=C(C)C)C(O[Si](C)(C)C)=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C)C(=O)O2 | 3154.5 | Semi standard non polar | 33892256 | Glycycoumarin,1TBDMS,isomer #1 | COC1=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C=C(C1=CC=C(O)C=C1O)C(=O)O2 | 3561.7 | Semi standard non polar | 33892256 | Glycycoumarin,1TBDMS,isomer #2 | COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C)C(=O)O2 | 3513.3 | Semi standard non polar | 33892256 | Glycycoumarin,1TBDMS,isomer #3 | COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O)C(=O)O2 | 3531.5 | Semi standard non polar | 33892256 | Glycycoumarin,2TBDMS,isomer #1 | COC1=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O)C(=O)O2 | 3662.5 | Semi standard non polar | 33892256 | Glycycoumarin,2TBDMS,isomer #2 | COC1=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C=C(C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C)C(=O)O2 | 3629.1 | Semi standard non polar | 33892256 | Glycycoumarin,2TBDMS,isomer #3 | COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C)C(=O)O2 | 3638.1 | Semi standard non polar | 33892256 | Glycycoumarin,3TBDMS,isomer #1 | COC1=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C)C(=O)O2 | 3781.9 | 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 - Glycycoumarin GC-MS (Non-derivatized) - 70eV, Positive | splash10-0fe3-1019000000-282ddd8e8c26f5157190 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Glycycoumarin GC-MS (3 TMS) - 70eV, Positive | splash10-00vi-1000090000-c783ed22b161225cef62 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Glycycoumarin GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Glycycoumarin 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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Experimental LC-MS/MS | LC-MS/MS Spectrum - Glycycoumarin 6V, Positive-QTOF | splash10-014i-0239000000-d9d32e4f7d08239440a1 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Glycycoumarin 6V, Negative-QTOF | splash10-014i-0139000000-a756c8040aba88b4cf47 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glycycoumarin 10V, Positive-QTOF | splash10-014i-0019000000-e8f5e2687e5267423792 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glycycoumarin 20V, Positive-QTOF | splash10-02t9-2019000000-d045204802bd0020e448 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glycycoumarin 40V, Positive-QTOF | splash10-014i-7192000000-e9862c4ef6e27eeb4017 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glycycoumarin 10V, Negative-QTOF | splash10-014i-0009000000-20b68087ed6e95096b14 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glycycoumarin 20V, Negative-QTOF | splash10-066r-0329000000-c3865e9020277be80782 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glycycoumarin 40V, Negative-QTOF | splash10-0a4i-4921000000-1394f8833dcd0fe74eec | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glycycoumarin 10V, Negative-QTOF | splash10-014i-0009000000-53fb202c32e20191eab9 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glycycoumarin 20V, Negative-QTOF | splash10-014r-0019000000-0adc5122ed4fb3bdacc4 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glycycoumarin 40V, Negative-QTOF | splash10-01bi-0029000000-174c1e96872b10850e45 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glycycoumarin 10V, Positive-QTOF | splash10-02t9-0009000000-ae0ab568c3686266872c | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glycycoumarin 20V, Positive-QTOF | splash10-03di-0019000000-726729680437cd2b03a4 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glycycoumarin 40V, Positive-QTOF | splash10-015a-0093000000-7fbdb116445186172827 | 2021-09-22 | Wishart Lab | View Spectrum |
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