Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:11:53 UTC |
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Update date | 2019-11-26 03:11:43 UTC |
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Primary ID | FDB015507 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Luteone |
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Description | Luteone, also known as ruizgenin, 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 lipid molecule. Luteone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Luteone has been detected, but not quantified in, several different foods, such as common beans, lima beans, pulses, and white lupines. This could make luteone a potential biomarker for the consumption of these foods. |
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CAS Number | 41743-56-0 |
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Structure | |
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Synonyms | Synonym | 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 | 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 | 3-(2,4-Dihydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one, 9CI | db_source | Luteone | biospider | Luteone (isoflavone) | biospider |
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Predicted Properties | |
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Chemical Formula | C20H18O6 |
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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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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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Isomeric 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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Average Molecular Weight | 354.3533 |
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Monoisotopic Molecular Weight | 354.110338308 |
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Classification |
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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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Disposition | Route of exposure: Biological location: Source: |
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Role | Biological role: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | C 67.79%; H 5.12%; O 27.09% | DFC |
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Melting Point | Mp 225-227° | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | 337 () (MeOH-NaOH) (Berdy) | DFC |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-004l-2019000000-e7c452eda2f10db25c9c | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive | splash10-004i-1000039000-76d13aaed8969b7e1f29 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-0019000000-cb91f2e2808608ed708b | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-05mk-3159000000-a8c6a86cb19263f22104 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0gb9-9784000000-01cb188e86ce2e000521 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0009000000-9551472e266098511e47 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0339000000-a6058217e23e60cb0aea | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-6911000000-38814121556ba6c764d5 | JSpectraViewer |
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External Links |
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ChemSpider ID | 4445109 |
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ChEMBL ID | CHEMBL549617 |
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KEGG Compound ID | C10498 |
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Pubchem Compound ID | 5281797 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 27917 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB36595 |
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CRC / DFC (Dictionary of Food Compounds) ID | KCW78-A:KCW78-A |
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EAFUS ID | Not Available |
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Dr. Duke ID | LUTEONE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00002545 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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anti feedant | | | DUKE | fungicide | 24127 | A substance used to destroy fungal pests. | DUKE | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | phytoalexin | 26115 | A toxin made by a plant that acts against an organism attacking it. | DUKE |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181. — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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