Coumestrol
From DrugPedia: A Wikipedia for Drug discovery
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| - | == | + | [http://crdd.osdd.net/raghava/hmrbase/test_extract.php?db=arun&table=nphormonet&id=1034&show=SHOW-3D Show 3-D Structure] |
| - | A daidzein derivative occurring naturally in forage crops which has some estrogenic activity. | + | {{Drugbox |
| + | | IUPAC_name = 3,9-dihydroxy-[1]benzoxolo[3,2-c]chromen-6-one | ||
| + | | CAS_number = 479-13-0 | ||
| + | | CAS_supplemental = | ||
| + | | ATC_suffix = | ||
| + | | ATC_supplemental = | ||
| + | | PubChem = 5281707 | ||
| + | | ChemSpiderID = | ||
| + | | chemical_formula =C<sub>1</sub><sub>5</sub>H<sub>8</sub>O<sub>5</sub> | ||
| + | | molecular_weight = 268.22 | ||
| + | | smiles = C1=CC2=C(C=C1O)OC3=C2C(=O)OC4=C3C=CC(=C4)O | ||
| + | | synonyms =Chrysanthin | ||
| + | | density = | ||
| + | | melting_point = 385(EXP) | ||
| + | | boiling_point = | ||
| + | | solubility = | ||
| + | | specific_rotation = | ||
| + | | sec_combustion = | ||
| + | | bioavailability = | ||
| + | | protein_bound = | ||
| + | | metabolism = | ||
| + | | elimination_half-life = | ||
| + | | excretion = | ||
| + | | pregnancy_category= | ||
| + | | dependency_liability = | ||
| + | | routes_of_administration = | ||
| + | }} | ||
| + | A daidzein derivative occurring naturally in forage crops which has some estrogenic activity.'''Coumestrol''' is a natural [[organic compound]] in the class of [[phytochemical]]s known as [[coumestan]]s. It has garnered research interest because of its estrogenic activity and its prevalence in some foods, such as [[soybean]]s and herbs such as [[Pueraria mirifica]]. | ||
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| + | Coumestrol was first identified by E. M. Bickoff in [[alfalfa]] in 1957.<ref>{{cite journal|title=Coumestrol, a New Estrogen Isolated from Forage Crops|author=E. M. Bickoff, A. N. Booth, R. L. Lyman, A. L. Livingston, C. R. Thompson, and F. Deeds|journal=Science|year=1957|volume=126|pages=969–970|doi=10.1126/science.126.3280.969-a}}</ref> It has since be found in a variety of [[legume]]s, [[soybean]]s, [[brussels sprout]]s, and [[spinach]]. [[Clover]] and soybeans have the highest concentrations.<ref name="Amin">{{cite journal|author=Amr Amin and Michael Buratovich|title="The Anti-Cancer Charm of Flavonoids: A Cup-of-Tea Will Do!|journal=Recent Patents on Anti-Cancer Drug Discovery|year=2007|issue=2|pages=109–117|doi=10.2174/157489207780832414|volume=2}}</ref> | ||
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| + | Coumestrol is a [[phytoestrogen]], mimicking the biological activity of [[estrogen]]s. The chemical shape of coumestrol orients its two [[hydroxy]] groups in the same position as the two hydroxy groups in [[estradiol]], allowing it to [[enzyme inhibition|inhibit]] the activity of [[aromatase]] and [[hydroxysteroid dehydrogenase]].<ref>{{cite journal|author=Blomquist CH, Lima PH, Hotchkiss JR|title=Inhibition of 3a-hydroxysteoid dehydogenase (3a-HSD) activity of human lung microsomes by genistein, daidzein, coumestrol and C18-, C19- and C21 hydroxysteroids and ketosteroids|journal=Steroids|year=2005|volume=70|issue=8|pages=507–514|doi=10.1016/j.steroids.2005.01.004}}</ref> These enzymes are involved in the biosynthesis of [[steroid]] hormones, and inhibition of these enzymes results in the modulation of hormone production.<ref name="Amin"/> | ||
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| + | '''Pueraria mirifica''' or White Kawo Krua has been found to contain concentration of Coumestrol where Cu<sup>2+</sup> at 1000 ppm the highest concentration was to be found where CuCl<sub>2</sub>, MnCl<sub>2</sub> and FeCl<sub>2</sub> at 1,000 ppm can in fact stimulate coumestrol accumulation. | ||
==General Properties== | ==General Properties== | ||
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<b>*Melting Point</b> | <b>*Melting Point</b> | ||
| - | 385(EXP | + | 385(EXP) |
<b>*LogP</b> | <b>*LogP</b> | ||
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| - | [[ | + | [[Category:Hormones]] |
| + | [[Category:HMRbase]] | ||
| + | [[Category:Flavonoids]] | ||
Current revision
|
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| Coumestrol
| |
| Systematic (IUPAC) name | |
| 3,9-dihydroxy-[1]benzoxolo[3,2-c]chromen-6-one | |
| Identifiers | |
| CAS number | |
| ATC code | ? |
| PubChem | |
| Chemical data | |
| Formula | C15H8O5 |
| Mol. mass | 268.22 |
| SMILES | & |
| Synonyms | Chrysanthin |
| Physical data | |
| Melt. point | 385(EXP) °C |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | ? |
| Half life | ? |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
? |
| Legal status | |
| Routes | ? |
A daidzein derivative occurring naturally in forage crops which has some estrogenic activity.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 was first identified by E. M. Bickoff in alfalfa in 1957.<ref>E. M. Bickoff, A. N. Booth, R. L. Lyman, A. L. Livingston, C. R. Thompson, and F. Deeds (1957). "Coumestrol, a New Estrogen Isolated from Forage Crops". Science 126: 969–970. doi:.</ref> It has since be found in a variety of legumes, soybeans, brussels sprouts, and spinach. Clover and soybeans have the highest concentrations.<ref name="Amin">Amr Amin and Michael Buratovich (2007). ""The Anti-Cancer Charm of Flavonoids: A Cup-of-Tea Will Do!". Recent Patents on Anti-Cancer Drug Discovery 2 (2): 109–117. doi:.</ref>
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.<ref>Blomquist CH, Lima PH, Hotchkiss JR (2005). "Inhibition of 3a-hydroxysteoid dehydogenase (3a-HSD) activity of human lung microsomes by genistein, daidzein, coumestrol and C18-, C19- and C21 hydroxysteroids and ketosteroids". Steroids 70 (8): 507–514. doi:.</ref> These enzymes are involved in the biosynthesis of steroid hormones, and inhibition of these enzymes results in the modulation of hormone production.<ref name="Amin"/>
Pueraria mirifica or White Kawo Krua has been found to contain concentration of Coumestrol where Cu2+ at 1000 ppm the highest concentration was to be found where CuCl2, MnCl2 and FeCl2 at 1,000 ppm can in fact stimulate coumestrol accumulation.
[edit] General Properties
*Molecular Weight
268.22
*Molecular Formula
C15H8O5
*IUPAC NAME
3,9-dihydroxy-[1]benzoxolo[3,2-c]chromen-6-one
*Canonical Smiles
C1=CC2=C(C=C1O)OC3=C2C(=O)OC4=C3C=CC(=C4)O
*Isomeric Smiles
[edit] PhysioChemical Properties
*Melting Point
385(EXP)
*LogP
1.57(EST)
*Water Solubility
