Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:00 UTC |
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Update date | 2019-11-26 02:56:35 UTC |
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Primary ID | FDB001539 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Eupatorin |
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Description | Eupatorin, also known as 3',5-dihydroxy-4',6,7-trimethoxyflavone, is a member of the class of compounds known as 7-o-methylated flavonoids. 7-o-methylated flavonoids are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, eupatorin is considered to be a flavonoid lipid molecule. Eupatorin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Eupatorin can be found in lemon verbena, mandarin orange (clementine, tangerine), and peppermint, which makes eupatorin a potential biomarker for the consumption of these food products. |
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CAS Number | 855-96-9 |
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Structure | |
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Synonyms | Synonym | Source |
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3',5-Dihydroxy-4',6,7-trimethoxyflavone | ChEBI | Eupatorine | ChEBI | 5,3'-Dihydroxy-6,7,4'-trimethoxyflavone | biospider | Flavone, 3',5-dihydroxy-4',6, 7-trimethoxy- | biospider | Flavone, 3',5-dihydroxy-4',6,7-trimethoxy- | biospider | Flavone, 3',5-dihydroxy-4',6,7-trimethoxy- (8CI) | biospider |
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Predicted Properties | |
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Chemical Formula | C18H16O7 |
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IUPAC name | 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,7-dimethoxy-4H-chromen-4-one |
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InChI Identifier | InChI=1S/C18H16O7/c1-22-12-5-4-9(6-10(12)19)13-7-11(20)16-14(25-13)8-15(23-2)18(24-3)17(16)21/h4-8,19,21H,1-3H3 |
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InChI Key | KLAOKWJLUQKWIF-UHFFFAOYSA-N |
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Isomeric SMILES | COC1=CC=C(C=C1O)C1=CC(=O)C2=C(O)C(OC)=C(OC)C=C2O1 |
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Average Molecular Weight | 344.3154 |
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Monoisotopic Molecular Weight | 344.089602866 |
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Classification |
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Description | Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. |
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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 | O-methylated flavonoids |
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Direct Parent | 7-O-methylated flavonoids |
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Alternative Parents | |
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Substituents | - 4p-methoxyflavonoid-skeleton
- 6-methoxyflavonoid-skeleton
- 7-methoxyflavonoid-skeleton
- 3'-hydroxyflavonoid
- 5-hydroxyflavonoid
- Flavone
- Hydroxyflavonoid
- Chromone
- Benzopyran
- Methoxyphenol
- 1-benzopyran
- Phenoxy compound
- Anisole
- Methoxybenzene
- Phenol ether
- Phenol
- 1-hydroxy-2-unsubstituted benzenoid
- Pyranone
- 1-hydroxy-4-unsubstituted benzenoid
- Alkyl aryl ether
- Benzenoid
- Pyran
- Monocyclic benzene moiety
- Vinylogous acid
- Heteroaromatic compound
- Organoheterocyclic compound
- Oxacycle
- Ether
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- 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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Ontology | No ontology term |
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Physico-Chemical Properties |
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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 | Not Available | |
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Melting Point | Not Available | |
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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 | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | Eupatorin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-01t9-0519000000-a21a64441f4e00e17d9a | Spectrum | Predicted GC-MS | Eupatorin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Eupatorin, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Eupatorin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Eupatorin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Eupatorin, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Eupatorin, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Eupatorin, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0009000000-5340e255afba6b4ed13e | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-0009000000-4a7b5ae3ef36e630c402 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00dj-3973000000-a5131327978e4f05c8a1 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0009000000-64f0f0ea9b22cc6f9fb0 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-0019000000-70fe2cf3e6f503057e58 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0ar4-0191000000-63c8e1cc35fb4cdd194d | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0009000000-5dc8eb0c39637af07086 | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-0009000000-5dc6fda56294b4fda1a7 | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-0229000000-ba2b53bbc55a5305ddc8 | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0009000000-72fbd0eb75bc9ea05c55 | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0f96-0009000000-176ea7d83528de995c1f | 2021-10-12 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | Not Available |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 97214 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | 277 |
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DrugBank ID | Not Available |
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HMDB ID | Not Available |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | EUPATORIN |
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BIGG ID | Not Available |
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KNApSAcK ID | C00003894 |
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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 bacterial | 33282 | An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis. | DUKE | Anti carcinomic | 35610 | An agent that inhibits the growth and proliferation of cancer cells, playing a crucial role in cancer prevention and treatment. Therapeutically, it is used to manage and treat various types of cancer, reducing tumor size and slowing disease progression, with key medical uses in oncology and chemotherapy. | DUKE | Anti-malarial | 33281 | An agent that prevents or treats malaria, a disease caused by Plasmodium parasites. It works by targeting the parasite's life cycle, reducing symptoms and preventing transmission. Therapeutically, anti-malarials are used to treat and prevent malaria, as well as to manage related conditions such as babesiosis and toxoplasmosis. | DUKE | Cytotoxic | 52209 | An agent that kills or damages cells, playing a biological role in immune responses and therapeutic applications in cancer treatment. Key medical uses include chemotherapy, targeting and destroying cancer cells, and treating certain autoimmune diseases by eliminating harmful cells. | DUKE | Emetic | | An agent that induces vomiting, playing a biological role in expelling toxins from the body. Therapeutically, it is used to treat poisoning, overdose, or gastrointestinal obstruction. Key medical uses include managing drug toxicity and aiding in stomach pumping procedures. | DUKE | Immunostimulant | 50847 | An agent that stimulates the immune system, enhancing its response to infections and diseases. Therapeutically, it boosts the body's natural defenses, commonly used to treat immunodeficiency disorders, prevent infections, and support cancer treatment, as well as manage chronic conditions like hepatitis and HIV. | DUKE | Parasiticide | | An agent that kills parasites, used in medicine and veterinary medicine to treat parasitic infections, particularly those caused by protozoa, helminths, and ectoparasites, playing a crucial role in managing diseases such as malaria, worms, and lice infestations. | DUKE | Plasmodicide | | An agent that kills malaria parasites, playing a crucial role in treating and preventing malaria. Therapeutically, it targets Plasmodium species, and its key medical uses include prophylaxis and treatment of malaria, particularly in endemic areas, helping to reduce transmission and alleviate disease burden. | 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 | — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070. — 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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