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 23:47:57 UTC |
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Update Date | 2022-03-07 02:55:47 UTC |
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HMDB ID | HMDB0038479 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Licoflavonol |
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Description | Licoflavonol belongs to the class of organic compounds known as 6-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 6-position. Thus, licoflavonol is considered to be a flavonoid. Licoflavonol has been detected, but not quantified in, herbs and spices. This could make licoflavonol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Licoflavonol. |
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Structure | CC(C)=CCC1=C(O)C2=C(OC(=C(O)C2=O)C2=CC=C(O)C=C2)C=C1O InChI=1S/C20H18O6/c1-10(2)3-8-13-14(22)9-15-16(17(13)23)18(24)19(25)20(26-15)11-4-6-12(21)7-5-11/h3-7,9,21-23,25H,8H2,1-2H3 |
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Synonyms | Value | Source |
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3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one | HMDB | 3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one, 9ci | HMDB | 4',5,7-Trihydroxy-6-prenylflavonol | HMDB |
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Chemical Formula | C20H18O6 |
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Average Molecular Weight | 354.3533 |
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Monoisotopic Molecular Weight | 354.110338308 |
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IUPAC Name | 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-en-1-yl)-4H-chromen-4-one |
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Traditional Name | licoflavonol |
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CAS Registry Number | 60197-60-6 |
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SMILES | CC(C)=CCC1=C(O)C2=C(OC(=C(O)C2=O)C2=CC=C(O)C=C2)C=C1O |
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InChI Identifier | InChI=1S/C20H18O6/c1-10(2)3-8-13-14(22)9-15-16(17(13)23)18(24)19(25)20(26-15)11-4-6-12(21)7-5-11/h3-7,9,21-23,25H,8H2,1-2H3 |
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InChI Key | TVMHBSODLWMMMV-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 6-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 6-position. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Flavonoids |
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Sub Class | Flavones |
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Direct Parent | 6-prenylated flavones |
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Alternative Parents | |
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Substituents | - 6-prenylated flavone
- 3-hydroxyflavone
- 3-hydroxyflavonoid
- 4'-hydroxyflavonoid
- 5-hydroxyflavonoid
- 7-hydroxyflavonoid
- Hydroxyflavonoid
- Chromone
- Benzopyran
- 1-benzopyran
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Pyranone
- Monocyclic benzene moiety
- Pyran
- Benzenoid
- Heteroaromatic compound
- Vinylogous acid
- Polyol
- Organoheterocyclic compound
- Oxacycle
- Organic oxygen compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- 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 | 185 - 187 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 4.61 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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Licoflavonol,1TMS,isomer #1 | CC(C)=CCC1=C(O)C=C2OC(C3=CC=C(O)C=C3)=C(O)C(=O)C2=C1O[Si](C)(C)C | 3426.3 | Semi standard non polar | 33892256 | Licoflavonol,1TMS,isomer #2 | CC(C)=CCC1=C(O)C=C2OC(C3=CC=C(O)C=C3)=C(O[Si](C)(C)C)C(=O)C2=C1O | 3420.7 | Semi standard non polar | 33892256 | Licoflavonol,1TMS,isomer #3 | CC(C)=CCC1=C(O)C=C2OC(C3=CC=C(O[Si](C)(C)C)C=C3)=C(O)C(=O)C2=C1O | 3486.8 | Semi standard non polar | 33892256 | Licoflavonol,1TMS,isomer #4 | CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=C(O)C=C3)=C(O)C(=O)C2=C1O | 3488.8 | Semi standard non polar | 33892256 | Licoflavonol,2TMS,isomer #1 | CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=C(O)C=C3)=C(O)C(=O)C2=C1O[Si](C)(C)C | 3332.1 | Semi standard non polar | 33892256 | Licoflavonol,2TMS,isomer #2 | CC(C)=CCC1=C(O)C=C2OC(C3=CC=C(O[Si](C)(C)C)C=C3)=C(O)C(=O)C2=C1O[Si](C)(C)C | 3324.6 | Semi standard non polar | 33892256 | Licoflavonol,2TMS,isomer #3 | CC(C)=CCC1=C(O)C=C2OC(C3=CC=C(O)C=C3)=C(O[Si](C)(C)C)C(=O)C2=C1O[Si](C)(C)C | 3287.5 | Semi standard non polar | 33892256 | Licoflavonol,2TMS,isomer #4 | CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=C(O)C=C3)=C(O[Si](C)(C)C)C(=O)C2=C1O | 3311.0 | Semi standard non polar | 33892256 | Licoflavonol,2TMS,isomer #5 | CC(C)=CCC1=C(O)C=C2OC(C3=CC=C(O[Si](C)(C)C)C=C3)=C(O[Si](C)(C)C)C(=O)C2=C1O | 3321.8 | Semi standard non polar | 33892256 | Licoflavonol,2TMS,isomer #6 | CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=C(O[Si](C)(C)C)C=C3)=C(O)C(=O)C2=C1O | 3372.2 | Semi standard non polar | 33892256 | Licoflavonol,3TMS,isomer #1 | CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=C(O[Si](C)(C)C)C=C3)=C(O)C(=O)C2=C1O[Si](C)(C)C | 3287.8 | Semi standard non polar | 33892256 | Licoflavonol,3TMS,isomer #2 | CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=C(O)C=C3)=C(O[Si](C)(C)C)C(=O)C2=C1O[Si](C)(C)C | 3230.7 | Semi standard non polar | 33892256 | Licoflavonol,3TMS,isomer #3 | CC(C)=CCC1=C(O)C=C2OC(C3=CC=C(O[Si](C)(C)C)C=C3)=C(O[Si](C)(C)C)C(=O)C2=C1O[Si](C)(C)C | 3227.7 | Semi standard non polar | 33892256 | Licoflavonol,3TMS,isomer #4 | CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=C(O[Si](C)(C)C)C=C3)=C(O[Si](C)(C)C)C(=O)C2=C1O | 3264.4 | Semi standard non polar | 33892256 | Licoflavonol,4TMS,isomer #1 | CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=C(O[Si](C)(C)C)C=C3)=C(O[Si](C)(C)C)C(=O)C2=C1O[Si](C)(C)C | 3279.7 | Semi standard non polar | 33892256 | Licoflavonol,1TBDMS,isomer #1 | CC(C)=CCC1=C(O)C=C2OC(C3=CC=C(O)C=C3)=C(O)C(=O)C2=C1O[Si](C)(C)C(C)(C)C | 3692.7 | Semi standard non polar | 33892256 | Licoflavonol,1TBDMS,isomer #2 | CC(C)=CCC1=C(O)C=C2OC(C3=CC=C(O)C=C3)=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O | 3689.8 | Semi standard non polar | 33892256 | Licoflavonol,1TBDMS,isomer #3 | CC(C)=CCC1=C(O)C=C2OC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)=C(O)C(=O)C2=C1O | 3713.9 | Semi standard non polar | 33892256 | Licoflavonol,1TBDMS,isomer #4 | CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=C(O)C=C3)=C(O)C(=O)C2=C1O | 3733.1 | Semi standard non polar | 33892256 | Licoflavonol,2TBDMS,isomer #1 | CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=C(O)C=C3)=C(O)C(=O)C2=C1O[Si](C)(C)C(C)(C)C | 3856.8 | Semi standard non polar | 33892256 | Licoflavonol,2TBDMS,isomer #2 | CC(C)=CCC1=C(O)C=C2OC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)=C(O)C(=O)C2=C1O[Si](C)(C)C(C)(C)C | 3845.1 | Semi standard non polar | 33892256 | Licoflavonol,2TBDMS,isomer #3 | CC(C)=CCC1=C(O)C=C2OC(C3=CC=C(O)C=C3)=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O[Si](C)(C)C(C)(C)C | 3819.0 | Semi standard non polar | 33892256 | Licoflavonol,2TBDMS,isomer #4 | CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=C(O)C=C3)=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O | 3847.4 | Semi standard non polar | 33892256 | Licoflavonol,2TBDMS,isomer #5 | CC(C)=CCC1=C(O)C=C2OC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O | 3864.8 | Semi standard non polar | 33892256 | Licoflavonol,2TBDMS,isomer #6 | CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)=C(O)C(=O)C2=C1O | 3884.1 | Semi standard non polar | 33892256 | Licoflavonol,3TBDMS,isomer #1 | CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)=C(O)C(=O)C2=C1O[Si](C)(C)C(C)(C)C | 4072.8 | Semi standard non polar | 33892256 | Licoflavonol,3TBDMS,isomer #2 | CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=C(O)C=C3)=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O[Si](C)(C)C(C)(C)C | 3943.5 | Semi standard non polar | 33892256 | Licoflavonol,3TBDMS,isomer #3 | CC(C)=CCC1=C(O)C=C2OC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O[Si](C)(C)C(C)(C)C | 3968.8 | Semi standard non polar | 33892256 | Licoflavonol,3TBDMS,isomer #4 | CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O | 4039.1 | Semi standard non polar | 33892256 | Licoflavonol,4TBDMS,isomer #1 | CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O[Si](C)(C)C(C)(C)C | 4164.3 | 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 - Licoflavonol GC-MS (Non-derivatized) - 70eV, Positive | splash10-004u-3039000000-183dc706a98c626c477b | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Licoflavonol GC-MS (4 TMS) - 70eV, Positive | splash10-004i-1000049000-e489cfd57a80662ca3ba | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Licoflavonol 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 - Licoflavonol 10V, Positive-QTOF | splash10-0a4i-0019000000-d8c640c9acec68b50410 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Licoflavonol 20V, Positive-QTOF | splash10-05mk-4069000000-43380ae555389ce529f3 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Licoflavonol 40V, Positive-QTOF | splash10-0100-6920000000-55834342d4fa547a52bc | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Licoflavonol 10V, Negative-QTOF | splash10-0udi-0019000000-1df2a7cc85a66e265345 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Licoflavonol 20V, Negative-QTOF | splash10-0udi-1139000000-71accf4da223a86aa27b | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Licoflavonol 40V, Negative-QTOF | splash10-054o-2911000000-9e28025ba9cf9ff708d0 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Licoflavonol 10V, Negative-QTOF | splash10-0udi-0009000000-d107cce4cd92eaf9a31e | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Licoflavonol 20V, Negative-QTOF | splash10-0udi-0049000000-65698d2a734eb4d92652 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Licoflavonol 40V, Negative-QTOF | splash10-0gi3-3493000000-204240cd34fe0a8989b7 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Licoflavonol 10V, Positive-QTOF | splash10-0a4i-0009000000-b1e99b126fa654ba9739 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Licoflavonol 20V, Positive-QTOF | splash10-0a4i-0009000000-4ad7ea5de243b6382682 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Licoflavonol 40V, Positive-QTOF | splash10-05fr-2194000000-89057208954378d066e9 | 2021-09-25 | Wishart Lab | View Spectrum |
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