Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:09:56 UTC |
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Update date | 2019-11-26 03:05:54 UTC |
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Primary ID | FDB011998 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Medicagol |
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Description | Medicagol belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. Thus, medicagol is considered to be a flavonoid lipid molecule. Medicagol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Medicagol has been detected, but not quantified in, several different foods, such as chickpea, pulses, herbs and spices, alfalfa, and cereals and cereal products. This could make medicagol a potential biomarker for the consumption of these foods. |
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CAS Number | 1983-72-8 |
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Structure | |
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Synonyms | Synonym | Source |
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3-Hydroxy-6H-[1,3]dioxolo[5,6]benzofuro[3,2-c][1]-benzopyran-6-one, 9ci | HMDB | 3-Hydroxy-8,9-methylenedioxycoumestan | HMDB | 7-Hydroxy-11,12-methylenedioxycoumestan | HMDB | 7-Hydroxy-5',6'-methylenedioxybenzofurano[3',2':3,4]coumarin | HMDB | 3-Hydroxy-6H-[1,3]dioxolo[5,6]benzofuro[3,2-c][1]-benzopyran-6-one, 9CI | db_source |
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Predicted Properties | |
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Chemical Formula | C16H8O6 |
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IUPAC name | 16-hydroxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2,4(8),9,13(18),14,16-heptaen-20-one |
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InChI Identifier | InChI=1S/C16H8O6/c17-7-1-2-8-10(3-7)22-16(18)14-9-4-12-13(20-6-19-12)5-11(9)21-15(8)14/h1-5,17H,6H2 |
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InChI Key | URMVEUAWRUQHON-UHFFFAOYSA-N |
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Isomeric SMILES | OC1=CC2=C(C=C1)C1=C(C3=CC4=C(OCO4)C=C3O1)C(=O)O2 |
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Average Molecular Weight | 296.2311 |
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Monoisotopic Molecular Weight | 296.032087988 |
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Classification |
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Description | belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. |
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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 | Coumestans |
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Direct Parent | Coumestans |
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Alternative Parents | |
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Substituents | - Coumestan
- Angular furanocoumarin
- Furanocoumarin
- Coumarin
- Benzopyran
- 1-benzopyran
- Benzodioxole
- Benzofuran
- Furopyran
- 1-hydroxy-2-unsubstituted benzenoid
- Pyranone
- Benzenoid
- Pyran
- Heteroaromatic compound
- Furan
- Lactone
- Acetal
- Oxacycle
- Organoheterocyclic compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Organooxygen 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: Source: Biological location: |
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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 64.87%; H 2.72%; O 32.41% | DFC |
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Melting Point | Mp 324-325° (337°) | 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 | Not Available | |
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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 | splash10-0002-0090000000-a27156413a82b2896b34 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00di-5239000000-a9c7b2d5e4247055cf19 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0090000000-9e260f2a78964c96d248 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-0090000000-f3ea38dbbb02ebbaa19d | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0uxr-0090000000-66fc3c899f2a8ff81a72 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0090000000-07cbe8cbbe681a4d18ed | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-0090000000-12c8d5ab4a4d80ea5677 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0002-1090000000-b9e2a75b068f0418b327 | JSpectraViewer |
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External Links |
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ChemSpider ID | 4477641 |
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ChEMBL ID | CHEMBL99941 |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 5319322 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB33831 |
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CRC / DFC (Dictionary of Food Compounds) ID | HCK71-E:HCK71-E |
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EAFUS ID | Not Available |
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Dr. Duke ID | MEDICAGOL |
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BIGG ID | Not Available |
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KNApSAcK ID | C00009760 |
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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 ulcer | 49201 | One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract. | 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 |
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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 | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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