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 21:45:15 UTC |
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Update Date | 2022-03-07 02:54:58 UTC |
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HMDB ID | HMDB0036595 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Luteone |
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Description | Luteone belongs to the class of organic compounds known as 6-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 6-position. Thus, luteone is considered to be a flavonoid. Luteone has been detected, but not quantified in, several different foods, such as common beans (Phaseolus vulgaris), lima beans (Phaseolus lunatus), pulses, and white lupines (Lupinus albus). This could make luteone a potential biomarker for the consumption of these foods. Luteone 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 small amount of articles have been published on Luteone. |
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Structure | CC(C)=CCC1=C(O)C2=C(OC=C(C2=O)C2=C(O)C=C(O)C=C2)C=C1O InChI=1S/C20H18O6/c1-10(2)3-5-13-16(23)8-17-18(19(13)24)20(25)14(9-26-17)12-6-4-11(21)7-15(12)22/h3-4,6-9,21-24H,5H2,1-2H3 |
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Synonyms | Value | Source |
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3-(2,4-Dihydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one | ChEBI | 3-(2,4-Dihydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one, 9ci | HMDB | Luteone? | HMDB | Ruizgenin | HMDB, MeSH | Ruizgenin, (3beta,5alpha,6alpha,25R)-isomer | MeSH | Ruizgenin, (3beta,5alpha,6alpha,25S)-isomer | MeSH | 5 beta-Spirostane-3 beta,6 alpha-diol | MeSH | Ruizgenin, (3beta,5alpha,6beta,25R)-isomer | MeSH |
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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-(2,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methylbut-2-en-1-yl)-4H-chromen-4-one |
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Traditional Name | luteone |
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CAS Registry Number | 41743-56-0 |
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SMILES | CC(C)=CCC1=C(O)C2=C(OC=C(C2=O)C2=C(O)C=C(O)C=C2)C=C1O |
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InChI Identifier | InChI=1S/C20H18O6/c1-10(2)3-5-13-16(23)8-17-18(19(13)24)20(25)14(9-26-17)12-6-4-11(21)7-15(12)22/h3-4,6-9,21-24H,5H2,1-2H3 |
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InChI Key | MMPVAPMCVABQPS-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 6-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit 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 | Isoflavonoids |
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Sub Class | Isoflavans |
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Direct Parent | 6-prenylated isoflavanones |
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Alternative Parents | |
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Substituents | - 6-prenylated isoflavanone
- Hydroxyisoflavonoid
- Isoflavone
- Chromone
- Benzopyran
- 1-benzopyran
- Resorcinol
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Pyranone
- Monocyclic benzene moiety
- Pyran
- Benzenoid
- Heteroaromatic compound
- Vinylogous acid
- 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 | 225 - 227 °C | 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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Luteone,1TMS,isomer #1 | CC(C)=CCC1=C(O)C=C2OC=C(C3=CC=C(O)C=C3O)C(=O)C2=C1O[Si](C)(C)C | 3326.9 | Semi standard non polar | 33892256 | Luteone,1TMS,isomer #2 | CC(C)=CCC1=C(O)C=C2OC=C(C3=CC=C(O)C=C3O[Si](C)(C)C)C(=O)C2=C1O | 3355.4 | Semi standard non polar | 33892256 | Luteone,1TMS,isomer #3 | CC(C)=CCC1=C(O)C=C2OC=C(C3=CC=C(O[Si](C)(C)C)C=C3O)C(=O)C2=C1O | 3370.0 | Semi standard non polar | 33892256 | Luteone,1TMS,isomer #4 | CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC=C(C3=CC=C(O)C=C3O)C(=O)C2=C1O | 3361.9 | Semi standard non polar | 33892256 | Luteone,2TMS,isomer #1 | CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC=C(C3=CC=C(O)C=C3O)C(=O)C2=C1O[Si](C)(C)C | 3243.0 | Semi standard non polar | 33892256 | Luteone,2TMS,isomer #2 | CC(C)=CCC1=C(O)C=C2OC=C(C3=CC=C(O[Si](C)(C)C)C=C3O)C(=O)C2=C1O[Si](C)(C)C | 3219.9 | Semi standard non polar | 33892256 | Luteone,2TMS,isomer #3 | CC(C)=CCC1=C(O)C=C2OC=C(C3=CC=C(O)C=C3O[Si](C)(C)C)C(=O)C2=C1O[Si](C)(C)C | 3216.3 | Semi standard non polar | 33892256 | Luteone,2TMS,isomer #4 | CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC=C(C3=CC=C(O)C=C3O[Si](C)(C)C)C(=O)C2=C1O | 3233.4 | Semi standard non polar | 33892256 | Luteone,2TMS,isomer #5 | CC(C)=CCC1=C(O)C=C2OC=C(C3=CC=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C2=C1O | 3246.7 | Semi standard non polar | 33892256 | Luteone,2TMS,isomer #6 | CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC=C(C3=CC=C(O[Si](C)(C)C)C=C3O)C(=O)C2=C1O | 3230.9 | Semi standard non polar | 33892256 | Luteone,3TMS,isomer #1 | CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC=C(C3=CC=C(O[Si](C)(C)C)C=C3O)C(=O)C2=C1O[Si](C)(C)C | 3172.6 | Semi standard non polar | 33892256 | Luteone,3TMS,isomer #2 | CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC=C(C3=CC=C(O)C=C3O[Si](C)(C)C)C(=O)C2=C1O[Si](C)(C)C | 3163.7 | Semi standard non polar | 33892256 | Luteone,3TMS,isomer #3 | CC(C)=CCC1=C(O)C=C2OC=C(C3=CC=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C2=C1O[Si](C)(C)C | 3155.4 | Semi standard non polar | 33892256 | Luteone,3TMS,isomer #4 | CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC=C(C3=CC=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C2=C1O | 3164.0 | Semi standard non polar | 33892256 | Luteone,4TMS,isomer #1 | CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC=C(C3=CC=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C2=C1O[Si](C)(C)C | 3161.6 | Semi standard non polar | 33892256 | Luteone,1TBDMS,isomer #1 | CC(C)=CCC1=C(O)C=C2OC=C(C3=CC=C(O)C=C3O)C(=O)C2=C1O[Si](C)(C)C(C)(C)C | 3651.3 | Semi standard non polar | 33892256 | Luteone,1TBDMS,isomer #2 | CC(C)=CCC1=C(O)C=C2OC=C(C3=CC=C(O)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O | 3634.5 | Semi standard non polar | 33892256 | Luteone,1TBDMS,isomer #3 | CC(C)=CCC1=C(O)C=C2OC=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O)C(=O)C2=C1O | 3642.1 | Semi standard non polar | 33892256 | Luteone,1TBDMS,isomer #4 | CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC=C(C3=CC=C(O)C=C3O)C(=O)C2=C1O | 3655.1 | Semi standard non polar | 33892256 | Luteone,2TBDMS,isomer #1 | CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC=C(C3=CC=C(O)C=C3O)C(=O)C2=C1O[Si](C)(C)C(C)(C)C | 3770.3 | Semi standard non polar | 33892256 | Luteone,2TBDMS,isomer #2 | CC(C)=CCC1=C(O)C=C2OC=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O)C(=O)C2=C1O[Si](C)(C)C(C)(C)C | 3763.8 | Semi standard non polar | 33892256 | Luteone,2TBDMS,isomer #3 | CC(C)=CCC1=C(O)C=C2OC=C(C3=CC=C(O)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O[Si](C)(C)C(C)(C)C | 3731.2 | Semi standard non polar | 33892256 | Luteone,2TBDMS,isomer #4 | CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC=C(C3=CC=C(O)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O | 3755.8 | Semi standard non polar | 33892256 | Luteone,2TBDMS,isomer #5 | CC(C)=CCC1=C(O)C=C2OC=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O | 3782.6 | Semi standard non polar | 33892256 | Luteone,2TBDMS,isomer #6 | CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O)C(=O)C2=C1O | 3784.4 | Semi standard non polar | 33892256 | Luteone,3TBDMS,isomer #1 | CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O)C(=O)C2=C1O[Si](C)(C)C(C)(C)C | 3869.4 | Semi standard non polar | 33892256 | Luteone,3TBDMS,isomer #2 | CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC=C(C3=CC=C(O)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O[Si](C)(C)C(C)(C)C | 3826.4 | Semi standard non polar | 33892256 | Luteone,3TBDMS,isomer #3 | CC(C)=CCC1=C(O)C=C2OC=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O[Si](C)(C)C(C)(C)C | 3847.5 | Semi standard non polar | 33892256 | Luteone,3TBDMS,isomer #4 | CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O | 3886.3 | Semi standard non polar | 33892256 | Luteone,4TBDMS,isomer #1 | CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O[Si](C)(C)C(C)(C)C | 3995.5 | 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 - Luteone GC-MS (Non-derivatized) - 70eV, Positive | splash10-004l-2019000000-e7c452eda2f10db25c9c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Luteone GC-MS (4 TMS) - 70eV, Positive | splash10-004i-1000039000-76d13aaed8969b7e1f29 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Luteone 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 - Luteone 10V, Positive-QTOF | splash10-0a4i-0019000000-cb91f2e2808608ed708b | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Luteone 20V, Positive-QTOF | splash10-05mk-3159000000-a8c6a86cb19263f22104 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Luteone 40V, Positive-QTOF | splash10-0gb9-9784000000-01cb188e86ce2e000521 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Luteone 10V, Negative-QTOF | splash10-0udi-0009000000-9551472e266098511e47 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Luteone 20V, Negative-QTOF | splash10-0udi-0339000000-a6058217e23e60cb0aea | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Luteone 40V, Negative-QTOF | splash10-0a4i-6911000000-38814121556ba6c764d5 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Luteone 10V, Negative-QTOF | splash10-0udi-0009000000-b3503695056246b53ddc | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Luteone 20V, Negative-QTOF | splash10-0udi-0019000000-09ce16917cfa9da61560 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Luteone 40V, Negative-QTOF | splash10-001i-2792000000-ec230273cd7094fcda33 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Luteone 10V, Positive-QTOF | splash10-0002-0090000000-0e40d1dc69d66b601127 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Luteone 20V, Positive-QTOF | splash10-0002-0090000000-f95cd7f394c37bd65111 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Luteone 40V, Positive-QTOF | splash10-009t-0190000000-062259ae8fdd318edbaf | 2021-09-24 | Wishart Lab | View Spectrum |
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