| Record Information |
|---|
| Version | 1.0 |
|---|
| Creation date | 2010-04-08 22:09:45 UTC |
|---|
| Update date | 2019-11-26 03:05:13 UTC |
|---|
| Primary ID | FDB011663 |
|---|
| Secondary Accession Numbers | Not Available |
|---|
| Chemical Information |
|---|
| FooDB Name | Coumestrol |
|---|
| Description | Isolated from Medicago subspecies, Glycine max (soybean), Pisum sativum (pea), Spinacia oleracea (spinach), Brassica oleracea (cabbage), Dolichos biflorus (papadi), Melilotus alba (white melilot), Phaseolus subspecies (inc. lima beans, pinto beans) and Vigna unguiculata (all Leguminosae). Potential nutriceutical
Coumestrol is a natural organic compound in the class of phytochemicals known as coumestans. It has garnered research interest because of its estrogenic activity and its prevalence in some foods, such as soybeans and herbs such as Pueraria mirifica.; Coumestrol is a phytoestrogen, mimicking the biological activity of estrogens. The chemical shape of coumestrol orients its two hydroxy groups in the same position as the two hydroxy groups in estradiol, allowing it to inhibit the activity of aromatase and hydroxysteroid dehydrogenase. These enzymes are involved in the biosynthesis of steroid hormones, and inhibition of these enzymes results in the modulation of hormone production.; Coumestrol, a coumestan isoflavone, has estrogenic properties (phytoestrogens are compounds structurally and functionally similar to 17-estradiol) and is an isoflavonoid phytoalexin produced by soybeans, a low molecular weight antimicrobial compound that is synthesized de novo and accumulates in plants after exposure to microorganisms (i.e.: phytoalexin induction and accumulation in soybean cotyledon tissue is observed with four species of Aspergillus: A. sojae, A. oryzae, A. niger, and A. flavus.). (PMID: 10888516); Coumestrol is a naturally occurring plant coumarin that displays high affinity for the hormone-binding site of the human estrogen receptor (hER), for which it serves as a potent non-steroidal agonist. Coumestrol emits intense blue fluorescence when bound to this protein, making it ideally suited for use as a cytological stain to detect ER in fixed and intact cells. Such observations illustrate the potential for using coumestrol to investigate real-time effects of a variety of physiological stimuli on the subcellular distribution of hER in living cells. (PMID: 8315272). Coumestrol is found in many foods, some of which are green bean, miso, other soy product, and fruits. |
|---|
| CAS Number | 479-13-0 |
|---|
| Structure | |
|---|
| Synonyms | | Synonym | Source |
|---|
| 3,9-Dihydroxycoumestan | ChEBI | | Chrysanthin | ChEBI | | 3,9-Dihydroxy-6H-[1]benzofuro[3,2-c]chromen-6-one | HMDB | | Coumestrol | HMDB | | Cumoesterol | HMDB | | 3,9-Dihydroxy-6-oxopterocarpen (obsol.) | db_source | | 3,9-Dihydroxy-6H-benzofuro(3,2-c)(1)benzopyran-6-one | biospider | | 3,9-Dihydroxy-6H-benzofuro[3,2-c][1]benzopyran-6-one, 9CI | db_source | | 6',7-Dihydroxybenzofuro[3',2',3,4]coumarin (obsol.) | db_source | | 6H-Benzofuro(3,2-c)(1)benzopyran-6-one, 3,9-dihydroxy- | biospider | | 6H-Benzofuro[3,2-c][1]benzopyran-6-one, 3,9-dihydroxy- | biospider | | 7,12-Dihydroxycoumestan | biospider | | 7,12-Dihydroxycoumestan (obsol.) | db_source | | Cumoestrol | biospider | | Cumostrol | db_source |
|
|---|
| Predicted Properties | |
|---|
| Chemical Formula | C15H8O5 |
|---|
| IUPAC name | 5,14-dihydroxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-9-one |
|---|
| InChI Identifier | InChI=1S/C15H8O5/c16-7-1-3-9-11(5-7)19-14-10-4-2-8(17)6-12(10)20-15(18)13(9)14/h1-6,16-17H |
|---|
| InChI Key | ZZIALNLLNHEQPJ-UHFFFAOYSA-N |
|---|
| Isomeric SMILES | OC1=CC2=C(C=C1)C1=C(O2)C2=C(OC1=O)C=C(O)C=C2 |
|---|
| Average Molecular Weight | 268.224 |
|---|
| Monoisotopic Molecular Weight | 268.037173358 |
|---|
| Classification |
|---|
| 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. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Phenylpropanoids and polyketides |
|---|
| Class | Isoflavonoids |
|---|
| Sub Class | Coumestans |
|---|
| Direct Parent | Coumestans |
|---|
| Alternative Parents | |
|---|
| Substituents | - Coumestan
- Angular furanocoumarin
- Furanocoumarin
- Coumarin
- Benzopyran
- 1-benzopyran
- Benzofuran
- Furopyran
- 1-hydroxy-2-unsubstituted benzenoid
- Pyranone
- Pyran
- Benzenoid
- Furan
- Heteroaromatic compound
- Lactone
- Organoheterocyclic compound
- Oxacycle
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Aromatic heteropolycyclic compound
|
|---|
| Molecular Framework | Aromatic heteropolycyclic compounds |
|---|
| External Descriptors | |
|---|
| Ontology |
|---|
|
| Disposition | Route of exposure: Source: Biological location: |
|---|
| Physico-Chemical Properties |
|---|
| Physico-Chemical Properties - Experimental | | Property | Value | Reference |
|---|
| Physical state | Solid | |
|---|
| Physical Description | Not Available | |
|---|
| Mass Composition | C 67.17%; H 3.01%; O 29.82% | DFC |
|---|
| Melting Point | Mp 385° | DFC |
|---|
| Boiling Point | Not Available | |
|---|
| Experimental Water Solubility | Not Available | |
|---|
| Experimental logP | Not Available | |
|---|
| Experimental pKa | Not Available | |
|---|
| Isoelectric point | Not Available | |
|---|
| Charge | Not Available | |
|---|
| Optical Rotation | Not Available | |
|---|
| Spectroscopic UV Data | 385 () (NaOH) (Berdy) | DFC |
|---|
| Density | Not Available | |
|---|
| Refractive Index | Not Available | |
|---|
|
|---|
| Spectra |
|---|
| Spectra | |
|---|
| EI-MS/GC-MS | | Type | Description | Splash Key | View |
|---|
| Predicted GC-MS | Coumestrol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00rf-0090000000-24d398554cf83008a0b2 | Spectrum | | Predicted GC-MS | Coumestrol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00di-3029000000-09e31fd7995c1524643c | Spectrum | | Predicted GC-MS | Coumestrol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
|
|---|
| MS/MS | | Type | Description | Splash Key | View |
|---|
| MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-014i-0090000000-3b007f8a59433c8c8102 | 2017-08-14 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-014i-0090000000-3b007f8a59433c8c8102 | 2017-08-14 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-014i-0090000000-5a91822fb14572c010a0 | 2017-08-14 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - ESI-TOF 40V, Negative | splash10-014i-0290000000-75cc1c58769101835d99 | 2017-08-14 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-014i-0290000000-75cc1c58769101835d99 | 2017-08-14 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - ESI-TOF 50V, Negative | splash10-0159-0960010000-fe04b8935dfef822b8ba | 2017-08-14 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-014i-0090000000-2a1a393fb92c1f28256e | 2017-09-12 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-014i-0090000000-606e78910a0367fb9798 | 2017-09-12 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-014i-0090000000-5a91822fb14572c010a0 | 2017-09-12 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - ESI-TOF 40V, Negative | splash10-014i-0290000000-75cc1c58769101835d99 | 2017-09-12 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-014i-0090000000-895c91406544dc79d34d | 2017-09-12 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - ESI-TOF 50V, Negative | splash10-0159-0960010000-fe04b8935dfef822b8ba | 2017-09-12 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-0904-3940000000-5bc2aef444fc6910fc19 | 2017-09-14 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-014i-0090000000-9fa59481d26b0a93d7c8 | 2017-09-14 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-014i-0090000000-2a1a393fb92c1f28256e | 2017-09-14 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-014i-0090000000-606e78910a0367fb9798 | 2017-09-14 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-014i-0090000000-5a91822fb14572c010a0 | 2017-09-14 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-014i-0290000000-75cc1c58769101835d99 | 2017-09-14 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-0159-0960010000-fe04b8935dfef822b8ba | 2017-09-14 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014i-0090000000-121d9805507777b81a75 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-014i-0090000000-b99e1506236f0fb0601d | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-004i-1490000000-9ba6d9042addda981b5b | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0090000000-a481cda3a4b436df23dd | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-0090000000-3606deabc4ddf6ecce16 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00di-0390000000-71b617f0a4545c7f72cc | 2016-08-03 | View Spectrum |
|
|---|
| NMR | Not Available |
|---|
| External Links |
|---|
| ChemSpider ID | 4445024 |
|---|
| ChEMBL ID | CHEMBL30707 |
|---|
| KEGG Compound ID | C10205 |
|---|
| Pubchem Compound ID | 5281707 |
|---|
| Pubchem Substance ID | Not Available |
|---|
| ChEBI ID | Not Available |
|---|
| Phenol-Explorer ID | 399 |
|---|
| DrugBank ID | Not Available |
|---|
| HMDB ID | HMDB02326 |
|---|
| CRC / DFC (Dictionary of Food Compounds) ID | GXS80-A:GXS80-A |
|---|
| EAFUS ID | Not Available |
|---|
| Dr. Duke ID | COUMESTROL |
|---|
| BIGG ID | Not Available |
|---|
| KNApSAcK ID | C00002514 |
|---|
| HET ID | CUE |
|---|
| Food Biomarker Ontology | Not Available |
|---|
| VMH ID | Not Available |
|---|
| Flavornet ID | Not Available |
|---|
| GoodScent ID | Not Available |
|---|
| SuperScent ID | Not Available |
|---|
| Wikipedia ID | Coumestrol |
|---|
| Phenol-Explorer Metabolite ID | 399 |
|---|
| Duplicate IDS | Not Available |
|---|
| Old DFC IDS | Not Available |
|---|
| Associated Foods |
|---|
| Food | Content Range | Average | Reference |
|---|
| Food | | | Reference |
|---|
|
| Biological Effects and Interactions |
|---|
| Health Effects / Bioactivities | | Descriptor | ID | Definition | Reference |
|---|
| Anti lipedemic | | An agent that reduces lipid levels in the blood, playing a crucial role in managing hyperlipidemia. Therapeutically, it helps prevent cardiovascular diseases by lowering cholesterol and triglyceride levels, making it a key treatment for conditions like atherosclerosis and hypertriglyceridemia. | DUKE | | Anti microbial | 33281 | An agent that inhibits the growth of microorganisms, such as bacteria, viruses, and fungi, playing a crucial role in preventing infections. Therapeutically, it is used to treat various infectious diseases, with key medical applications including wound care, respiratory infections, and gastrointestinal infections, ultimately reducing the risk of infection and promoting healing. | DUKE | | Anti osteoporotic | 52217 | An agent that prevents or treats osteoporosis by promoting bone density, reducing bone resorption, and increasing calcium absorption, commonly used in managing osteoporosis, osteopenia, and preventing fractures. | DUKE | | Estrogenic | | An agent that mimics the effects of estrogen, regulating female reproductive processes and development. Therapeutically, estrogenic agents are used in hormone replacement therapy, contraception, and treating menopausal symptoms, as well as certain cases of osteoporosis and infertility. | DUKE | | Fungicide | 24127 | An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage. | DUKE | | Hypocholesterolemic | | An agent that lowers cholesterol levels in the blood, playing a crucial role in preventing cardiovascular disease. Therapeutically, it is used to manage hyperlipidemia and reduce the risk of heart disease, with key medical applications including the treatment of high cholesterol, atherosclerosis, and coronary artery disease. | DUKE | | Nematicide | 25491 | An agent that kills nematodes, a type of parasitic worm, used to control infestations in crops and animals, with therapeutic applications in veterinary medicine to treat parasitic infections and promote livestock health. | DUKE | | Nematistat | | An agent that disorients, paralyzes, or confuses nematodes, preventing root infestation, with potential therapeutic applications in agriculture and key medical uses in managing parasitic nematode infections. | DUKE | | Peroxidase inhibitor | 23924 | An agent that blocks the activity of peroxidase enzymes, reducing oxidative stress and inflammation. Therapeutically, it has applications in managing conditions like cancer, neurodegenerative diseases, and cardiovascular disorders, where oxidative damage plays a key role. | DUKE | | Pesticide | 25944 | An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections. | DUKE | | Phytoalexin | 26115 | A plant-derived compound that plays a biological role in defense against pathogens. It has therapeutic applications as an antimicrobial, antioxidant, and anti-inflammatory agent, with key medical uses in managing infections, cancer, and neurodegenerative diseases. | DUKE | | Utero trophic | 52217 | A hormone that stimulates uterine growth and development, playing a crucial role in pregnancy. Therapeutically, it's used to support embryonic implantation and fetal development, with key medical applications in infertility treatments, such as in vitro fertilization (IVF) and recurrent miscarriage prevention. | DUKE | | Anti-oxidant | 22586 | An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects. | CHEBI |
|
|---|
| Enzymes | Not Available |
|---|
| Pathways | Not Available |
|---|
| Metabolism | Not Available |
|---|
| Biosynthesis | Not Available |
|---|
| Organoleptic Properties |
|---|
| Flavours | | Flavor | Citations |
|---|
| bitter |
- Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
|
|
|---|
| Files |
|---|
| MSDS | show |
|---|
| References |
|---|
| Synthesis Reference | Not Available |
|---|
| General Reference | Not Available |
|---|
| Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— 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.
|
|---|
