| Revision as of 23:21, 6 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,044 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEBI').← Previous edit |
Latest revision as of 16:36, 23 September 2024 edit undoJWBE (talk | contribs)Extended confirmed users10,129 edits added Category:4-Methoxyphenyl compounds using HotCat |
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{{chembox |
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{{chembox |
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| verifiedrevid = 414030019 |
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| verifiedrevid = 443423335 |
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| name = Biochanin A |
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| ImageFile = Biochanin A.svg |
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| Name = Biochanin A |
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| ImageFile = Biochanin A.svg |
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| ImageSize = 250px |
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| ImageSize = 220px |
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| ImageFile1 = Biochanin-A-3D-balls.png |
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| IUPACName = 5,7-dihydroxy-3-(4-methoxyphenyl)chromen-4-one |
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| ImageSize1 = 220 |
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| OtherNames = Biochanin<br>4'-Methylgenistein<br>olmelin<br>Biochanine A<br>Biochanin-A<br>Genistein 4-methyl ether<br>5,7-Dihydroxy-4'-methoxyisoflavone |
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| ImageAlt1 = Biochanin A molecule |
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| Section1= {{Chembox Identifiers |
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| IUPACName = 5,7-Dihydroxy-4′-methoxyisoflavone |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| SystematicName = 5,7-Dihydroxy-3-(4-methoxyphenyl)-4''H''-1-benzopyran-4-one |
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| OtherNames = Biochanin<br />4′-Methylgenistein<br />olmelin<br />Biochanine A<br />Biochanin-A<br />Genistein 4-methyl ether |
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|Section1={{Chembox Identifiers |
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| IUPHAR_ligand = 2829 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 4444068 |
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| ChemSpiderID = 4444068 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 491-80-5 |
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| CASNo = 491-80-5 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem = 5280373 |
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| ChEBI = 17574 |
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| UNII = U13J6U390T |
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| PubChem = 5280373 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 17574 |
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| SMILES = O=C\1c3c(O/C=C/1c2ccc(OC)cc2)cc(O)cc3O |
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| SMILES = O=C\1c3c(O/C=C/1c2ccc(OC)cc2)cc(O)cc3O |
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| Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=16 | H=12 | O=5 |
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| Formula = C<sub>16</sub>H<sub>12</sub>O<sub>5</sub> |
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| Appearance = |
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| MolarMass = 284.26 g/mol |
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| Density = |
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| ExactMass = 284.068473 |
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| Solubility= |
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| MeltingPt = <!-- °C --> |
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|Section3= {{Chembox Hazards |
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'''Biochanin A''' is an ]. It is a natural organic compound in the class of ]s known as flavonoids. Biochanin A can be found in ] <ref> |
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'''Biochanin A''' is an ]. It is a natural organic compound in the class of ]s known as flavonoids. Biochanin A can be found in ]<ref>{{ cite journal |author1=Medjakovic, S. |author2=Jungbauer, A. | title = Red clover isoflavones biochanin A and formononetin are potent ligands of the human aryl hydrocarbon receptor | journal = The Journal of Steroid Biochemistry and Molecular Biology | year = 2008 | volume = 108 | issue = 1–2 | pages = 171–177 | pmid = 18060767 | doi = 10.1016/j.jsbmb.2007.10.001 |s2cid=206495959 }}</ref> in ], in ] sprouts, in ]s, in ] (''Cicer arietinum'') and in other legumes. |
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Biochanin A is classified as a ] and has putative benefits in dietary ]. |
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Biochanin A is classified as a ] and has putative benefits in dietary ].{{medcn|date=November 2015}} It has also been found to be a weak ] of ] '']''.<ref>{{cite journal | vauthors=Thors L, Burston JJ, Alter BJ, McKinney MK, Cravatt BF, Ross RA, Pertwee RG, Gereau RW, Wiley JL, Fowler CJ | title = Biochanin A, a naturally occurring inhibitor of fatty acid amide hydrolase | journal = British Journal of Pharmacology | year = 2010 | volume = 160 | issue = 3 | pages = 549–560 | doi = 10.1111/j.1476-5381.2010.00716.x | pmid = 20590565 | pmc = 2931556 }}</ref> |
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==Metabolism== |
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==Metabolism== |
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The enzyme ] uses ] and NADP+ to produce biochanin A, NADPH, and H+. |
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The enzyme ] uses dihydrobiochanin A and NADP<sup>+</sup> to produce biochanin A, NADPH, and H<sup>+</sup>. The enzyme ] uses malonyl-CoA and biochanin A 7-O-β-<small>D</small>-glucoside to produce CoA and biochanin A 7-O-(6-O-malonyl-β-<small>D</small>-glucoside). |
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The enzyme ] uses malonyl-CoA and biochanin A 7-O-beta-D-] to produce CoA and biochanin A 7-O-(6-O-]-beta-D-glucoside). |
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==References== |
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{{reflist}} |
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==See also== |
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==See also== |
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* ] |
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==References== |
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{{Isoflavone}} |
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{{Reflist}} |
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] |
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{{Isoflavones}} |
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{{Cannabinoid receptor modulators}} |
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] |
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{{Estrogen receptor modulators}} |
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] |
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{{Estrogen-related receptor modulators}} |
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