Biochanin A (BioCAD00000007461)

blood urine plant natural products microbial natural products

Metabolite Card

Formula: C16H12O5 (284.0685)
SMILES: COC1=CC=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O

Synonyms [en]

biochanin A; 5,7-Dihydroxy-4'-methoxyisoflavone; Pratensol; olmelin; 4'-Methylgenistein; genistein 4-methyl ether

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Biochanin A. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000007461). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

The phytoestrogen biochanin A is an isoflavone derivative isolated from red clover Trifolium pratense with anticarcinogenic properties. Treating MCF-7 human breast carcinoma cells with biochanin A alone caused the accumulation of CYP1A1 mRNA and an increase in CYP1A1-specific 7-ethoxyresorufin O-deethylase (EROD) activity in a dose dependent manner. Biochanin A may be a natural ligand to bind on aryl hydrocarbon receptor acting as an antagonist/agonist of the pathway. (PMID: 16903077). Biochanin A suppress nuclear factor-kappaB-driven interleukin-6 (IL6) expression. In addition to its physiologic immune function as an acute stress cytokine, sustained elevated expression levels of IL6 promote chronic inflammatory disorders, aging frailty, and tumorigenesis. (PMID: 16651441). Biochanin A induces a decrease in invasive activity of U87MG cells in a dose-related manner. (PMID: 16598420). Biochanin A activates peroxisome proliferator-activated receptors (PPAR) PPARalpha, PPARgamma, and adipocyte differentiation in vitro of 3T3-L1 preadipocytes, suggesting potential value of isoflavones, especially biochanin A and their parent botanicals, as antidiabetic agents and for use in regulating lipid metabolism. (PMID: 16549448).

Membrane
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 491-80-5
  • PubChem: 5280373
  • ChEBI: ChEBI:17574
  • HMDB: HMDB0002338
  • LipidMaps: LMPK12050229
  • KEGG: C00814
  • BioCyc: BIOCHANIN-A
  • NCBI MeSH: biochanin A
  • Wikipedia: Biochanin_A
  • DrugBank: DB15334
  • RefMet: RM0161350
  • MoNA: BML00747
  • MoNA: BML00754
  • MoNA: BML00761
  • MoNA: BML00767
  • MoNA: BML00772
  • MoNA: BML00777
  • MoNA: BML80820
  • MoNA: BML80821
  • MoNA: BML80822
  • MoNA: BML80823
  • MoNA: FiehnLib000581
  • MoNA: HMDB0002338_c_ms_2196
  • MoNA: HMDB0002338_ms_ms_285663
  • MoNA: HMDB0002338_ms_ms_285664
  • MoNA: HMDB0002338_ms_ms_285665
  • MoNA: HMDB0002338_ms_ms_285666
  • MoNA: HMDB0002338_ms_ms_285667
  • MoNA: LU096001
  • MoNA: LU096002
  • MoNA: LU096003
  • MoNA: LU096004
  • MoNA: LU096005
  • MoNA: LU096006
  • MoNA: LU096051
  • MoNA: LU096052
  • MoNA: LU096053
  • MoNA: LU096054
  • MoNA: LU096055
  • MoNA: LU096056
  • MoNA: MetaboBASE0038
  • MoNA: MetaboBASE0039
  • MoNA: MetaboBASE0040
  • MoNA: MetaboBASE0041
  • MoNA: MetaboBASE0042
  • MoNA: PB000241
  • MoNA: PB000261
  • MoNA: PB000262
  • MoNA: PB000263
  • MoNA: PB005707
  • MoNA: PB005708
  • MoNA: PB005709
  • MoNA: PB005710
  • MoNA: PB005711
  • MoNA: PM001308
  • MoNA: PN000108
  • MoNA: PN000109
  • MoNA: PR309428
  • MoNA: PR310861
  • MoNA: RIKENPlaSMA002075
  • MoNA: RIKENPlaSMA002078
  • MoNA: RIKENPlaSMA002082
  • MoNA: RIKENPlaSMA002086
  • MoNA: RIKENPlaSMA002090
  • MoNA: RIKENPlaSMA002093
  • MoNA: RIKENPlaSMA002097
  • MoNA: RIKENPlaSMA002100
  • MoNA: RIKENPlaSMA002104
  • MoNA: RIKENPlaSMA002108
  • MoNA: RIKENPlaSMA002112
  • MoNA: RIKENPlaSMA002116
  • MoNA: RIKENPlaSMA005637
  • MoNA: RIKENPlaSMA005642
  • MoNA: RIKENPlaSMA005647
  • MoNA: RIKENPlaSMA005652
  • MoNA: RIKENPlaSMA005656
  • MoNA: RIKENPlaSMA005661
  • MoNA: RIKENPlaSMA005665
  • MoNA: RIKENPlaSMA005670
  • MoNA: RIKENPlaSMA005675
  • MoNA: RIKENPlaSMA005680
  • MoNA: RIKENPlaSMA005684
  • MoNA: RIKENPlaSMA005688
  • MoNA: VF-NPL-LTQ003703
  • MoNA: VF-NPL-LTQ003704
  • MoNA: VF-NPL-LTQ003706
  • MoNA: VF-NPL-LTQ007147
  • MoNA: VF-NPL-LTQ007148
  • MoNA: VF-NPL-LTQ007150
  • MoNA: VF-NPL-QEHF013309
  • MoNA: VF-NPL-QEHF013310
  • MoNA: VF-NPL-QEHF013311
  • MoNA: VF-NPL-QEHF013312
  • MoNA: VF-NPL-QEHF013313
  • MoNA: VF-NPL-QEHF013314
  • MoNA: VF-NPL-QEHF013951
  • MoNA: VF-NPL-QEHF013952
  • MoNA: VF-NPL-QEHF013953
  • MoNA: VF-NPL-QEHF013954
  • MoNA: VF-NPL-QEHF013955
  • MoNA: VF-NPL-QEHF013956
  • MoNA: VF-NPL-QTOF006882
  • MoNA: VF-NPL-QTOF006883
  • MoNA: VF-NPL-QTOF006884
  • MoNA: VF-NPL-QTOF006885
  • MoNA: VF-NPL-QTOF006886
  • MoNA: VF-NPL-QTOF006887
  • Metlin: METLIN_43566
  • Coconut NaturalProduct: CNP0314566.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R02931 2.1.1.46 S-adenosyl-L-methionine: genistein 4'-O-methyltransferase
KEGG:R02954 1.3.1.46 dihydrobiochanin-A:NADP+ delta2-oxidoreductase
KEGG:R06561 1.14.14.90 biochanin A,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (2'-hydroxylating)
KEGG:R06795 2.4.1.170 UDP-glucose:isoflavone 7-O-beta-D-glucosyltransferase
KEGG:R07776 1.14.14.88 biochanin A,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (3'-hydroxylating)
BioCyc:BIOCHANIN-A-REDUCTASE-RXN 1.3.1.46 NADP + DIHYDROBIOCHANIN-A<=>NADPH + BIOCHANIN-A + 2 PROTON
BioCyc:RXN-3761 1.14.14.88 BIOCHANIN-A + OXYGEN-MOLECULE + Red-NADPH-Hemoprotein-Reductases --> CPD-3622 + Ox-NADPH-Hemoprotein-Reductases + WATER
BioCyc:RXN-3645 2.1.1.46 S-ADENOSYLMETHIONINE + CPD-3141 --> PROTON + BIOCHANIN-A + ADENOSYL-HOMO-CYS
BioCyc:RXN-5502 CPD-5421 --> BIOCHANIN-A + WATER
BioCyc:RXN-4705 CPD-4563 + WATER --> BIOCHANIN-A + Glucopyranose + PROTON
BioCyc:RXN-4702 2.4.1.170 CPD-12575 + BIOCHANIN-A --> CPD-4563 + UDP
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Organism Source

Taxonomy Source

  1. A new engineered strain of Bacillus subtilis [yyzE ypqE ptsG] [ncbi taxid: ]
  2. Abelia chinensis [ncbi taxid: 180068]
  3. Albizia procera [ncbi taxid: 384949]
  4. Anaxagorea luzonensis A.GRAY [ncbi taxid: ]
  5. Andira inermis [ncbi taxid: 53825]
  6. Andira parviflora [ncbi taxid: 588920]
  7. Annona squamosa [ncbi taxid: 301693]
  8. Apis mellifera ligustica [ncbi taxid: 7469]
  9. Aplophyllum alberti-regelii [ncbi taxid: ]
  10. Arachis hypogaea [ncbi taxid: 3818]
  11. Arum maximum [ncbi taxid: ]
  12. Asclepias vestita [ncbi taxid: 660014]
  13. Asimina parviflora [ncbi taxid: 137664]
  14. Aspilia parvifolia [ncbi taxid: ]
  15. Astragalus adsurgens [ncbi taxid: 20401]
  16. Astragalus membranaceus [ncbi taxid: 649199]
  17. Astragalus mongholicus [ncbi taxid: 119829]
  18. Atraphaxis spinosa [ncbi taxid: 137669]
  19. Baccharis neglecta [ncbi taxid: 41488]
  20. Baphicacanthus cusia [ncbi taxid: ]
  21. Baptisia alba [ncbi taxid: 313911]
  22. Baptisia calycosa [ncbi taxid: 1969220]
  23. Baptisia sphaerocarpa [ncbi taxid: 313914]
  24. Baptisia tinctoria [ncbi taxid: 49797]
  25. Barringtonia acutangula [ncbi taxid: 1090620]
  26. Bolusanthus specious [ncbi taxid: ]
  27. Brazilian Red Propolis [ncbi taxid: ]
  28. Cacospongia scalaris [ncbi taxid: ]
  29. Candida albicans [ncbi taxid: 5476]
  30. Caulis millettiae [ncbi taxid: ]
  31. Caulis spatholobi [ncbi taxid: ]
  32. Centaurea maculosa [ncbi taxid: 215693]
  33. Chamomilla recutita [ncbi taxid: ]
  34. Chondrodendron tomentosum [ncbi taxid: 461568]
  35. Cicer anatolicum [ncbi taxid: 242878]
  36. Cicer arietinum [ncbi taxid: 3827]
  37. Cicer bijugum [ncbi taxid: 90899]
  38. Cicer canariensis [ncbi taxid: ]
  39. Cicer chorassanicum [ncbi taxid: 107682]
  40. Cicer cuneatum [ncbi taxid: 92720]
  41. Cicer echinospermum [ncbi taxid: 90897]
  42. Cicer judaicum [ncbi taxid: 92719]
  43. Cicer judicum [ncbi taxid: ]
  44. Cicer macracanthum [ncbi taxid: 200949]
  45. Cicer microphyllum [ncbi taxid: 224826]
  46. Cicer mogolatvicum [ncbi taxid: ]
  47. Cicer montbretii [ncbi taxid: 242879]
  48. Cicer nuristanicum [ncbi taxid: 242870]
  49. Cicer oxyodon [ncbi taxid: 242871]
  50. Cicer pinnatifidum [ncbi taxid: 47088]
  51. Cicer pungens [ncbi taxid: 242872]
  52. Cicer rechingeri [ncbi taxid: 380786]
  53. Cicer reticulatum [ncbi taxid: 90898]
  54. Cicer songaricum [ncbi taxid: 242873]
  55. Cicer yamashitae [ncbi taxid: 92718]
  56. Citrus wilsonii [ncbi taxid: 475932]
  57. Clerodendrum bungei [ncbi taxid: 54211]
  58. Conus mus [ncbi taxid: 257335]
  59. Cordia leucocephala [ncbi taxid: ]
  60. Corydalis densiflora [ncbi taxid: ]
  61. Cotoneaster pannosus [ncbi taxid: 143397]
  62. Craibiodendron yunnanense [ncbi taxid: 49140]
  63. Croton megistocarpus [ncbi taxid: 425923]
  64. Cudrania tricuspidata [ncbi taxid: ]
  65. Cystoseira mediterranea [ncbi taxid: ]
  66. Dalbergia congestiflora [ncbi taxid: 77268]
  67. Dalbergia frutescens [ncbi taxid: 450026]
  68. Dalbergia lanceolaria [ncbi taxid: 1225666]
  69. Dalbergia nitidula [ncbi taxid: 1265830]
  70. Dalbergia parviflora [ncbi taxid: 1353466]
  71. Dalbergia sissoo [ncbi taxid: 107308]
  72. Dalbergia spruceana [ncbi taxid: 1353472]
  73. Dalbergia volubilis [ncbi taxid: 1544813]
  74. Dendronephthya griffini [ncbi taxid: ]
  75. Desmodium canadense [ncbi taxid: 932098]
  76. Diospyros assimilis [ncbi taxid: ]
  77. Dolabella californica [ncbi taxid: ]
  78. Echinospartum horridum [ncbi taxid: 238419]
  79. Embelia parviflora [ncbi taxid: 1341708]
  80. Embelia ribes [ncbi taxid: 459629]
  81. Embelia schimperi [ncbi taxid: 2595069]
  82. Ephedra sinica [ncbi taxid: 33152]
  83. Epilobium hirsutum [ncbi taxid: 210355]
  84. Eria anomala [ncbi taxid: ]
  85. Erysimum leptophyllum [ncbi taxid: 1492248]
  86. Erythrina melanacantha [ncbi taxid: 2590708]
  87. Esenbeckia leiocarpa [ncbi taxid: 1344466]
  88. Euphorbia nematocypha [ncbi taxid: ]
  89. Fallopia multiflora [ncbi taxid: 76025]
  90. Faramea salicifolia [ncbi taxid: ]
  91. Fructus psoraleae corylifoliae [ncbi taxid: ]
  92. Ganoderma lucidum [ncbi taxid: 5315]
  93. Ganoderma sinense [ncbi taxid: 36075]
  94. Geranium sibiricum [ncbi taxid: 345237]
  95. Glycine max [ncbi taxid: 3847]
  96. Glycyrrhiza uralensis [ncbi taxid: 74613]
  97. Gymnocalycium schickendantzii [ncbi taxid: 432501]
  98. Gynerium sagittatum [ncbi taxid: 42053]
  99. Halotydeus destructor [ncbi taxid: 2874060]
  100. Haplophyllum obtusifolium [ncbi taxid: 452779]
  101. Haplormosia monophylla [ncbi taxid: 1929972]
  102. Hedysarum multijugum [ncbi taxid: ]
  103. Helichrysum tenuifolium [ncbi taxid: 3030141]
  104. Heliotropium hirsutissimum [ncbi taxid: 168347]
  105. Herba acalyphae [ncbi taxid: ]
  106. Homo sapiens [ncbi taxid: 9606]
  107. Hypericum styphelioides [ncbi taxid: ]
  108. Inulanthera calva [ncbi taxid: 127985]
  109. Khaya grandifoliola [ncbi taxid: 859838]
  110. Klasea sogdiana [ncbi taxid: 354320]
  111. Knema glomerata [ncbi taxid: ]
  112. Lagerstroemia indica [ncbi taxid: 141186]
  113. Latrunculia magnifica [ncbi taxid: ]
  114. Lemaireocereus longispinus [ncbi taxid: ]
  115. Lupinus albus [ncbi taxid: 3870]
  116. Lycogala epidendrum [ncbi taxid: 300236]
  117. Lythrum salicaria [ncbi taxid: 13129]
  118. Mabea fistulifera [ncbi taxid: 1924986]
  119. Medicago sativa [ncbi taxid: 3879]
  120. Millettia dielsiana [ncbi taxid: ]
  121. Mirabilis jalapa [ncbi taxid: 3538]
  122. Moghania philippinensis [ncbi taxid: ]
  123. Monopterix inpae [ncbi taxid: ]
  124. Monsonia senegalensis [ncbi taxid: 163693]
  125. Morella rubra [ncbi taxid: 262757]
  126. Murraya exotica [ncbi taxid: 2901850]
  127. Murraya paniculata [ncbi taxid: 43711]
  128. Myristica malabarica [ncbi taxid: 741156]
  129. Myroxylon peruiferum [ncbi taxid: 1231556]
  130. Myxococcus stipitatus [ncbi taxid: 83455]
  131. Napoleonaea vogelii [ncbi taxid: 79577]
  132. Nicotiana raimondii [ncbi taxid: 200312]
  133. Ononis spinosa [ncbi taxid: 58890]
  134. Onopordum acanthium [ncbi taxid: 92915]
  135. Pancratium sickenbergeri [ncbi taxid: 693598]
  136. Pericopsis elata [ncbi taxid: 1079081]
  137. Pericopsis laxiflora [ncbi taxid: 1929974]
  138. Pericopsis mooniana [ncbi taxid: 53917]
  139. Persea kusanoi [ncbi taxid: ]
  140. Piper regnellii [ncbi taxid: 1427529]
  141. Planchonia grandis [ncbi taxid: ]
  142. Plathymenia reticulata [ncbi taxid: 148722]
  143. Podocarpus amarus [ncbi taxid: ]
  144. Pteridium esculentum [ncbi taxid: 32102]
  145. Pueraria montana [ncbi taxid: 132459]
  146. Pueraria montana var. lobata [ncbi taxid: 3893]
  147. Pueraria montana var. thomsonii [ncbi taxid: 174648]
  148. Retama raetam [ncbi taxid: 49837]
  149. Rhinella marina [ncbi taxid: 8386]
  150. Schleichera trijuga [ncbi taxid: 2871444]
  151. Schultesia guianensis [ncbi taxid: 84919]
  152. Scolopia chinensis [ncbi taxid: 1603833]
  153. Senecio isatideus [ncbi taxid: ]
  154. Shigella dysenteriae [ncbi taxid: 622]
  155. Simarouba glauca [ncbi taxid: 43729]
  156. Siphonaria capensis [ncbi taxid: 427274]
  157. Sophora flavescens [ncbi taxid: 49840]
  158. Sophora japonica [ncbi taxid: ]
  159. Sophora mollis [ncbi taxid: 3091532]
  160. Sophora secundiflora [ncbi taxid: ]
  161. Spatholobus suberectus [ncbi taxid: 455371]
  162. Streptomyces filamentosus [ncbi taxid: 67294]
  163. Swartzia polyphylla [ncbi taxid: 450104]
  164. Syzygium polycephaloides [ncbi taxid: ]
  165. Theonella conica [ncbi taxid: 1006816]
  166. Thermopsis macrophylla [ncbi taxid: 114322]
  167. Thermopsis rhombifolia [ncbi taxid: 61122]
  168. Tricholoma columbetta [ncbi taxid: 176010]
  169. Triclisia subcordata [ncbi taxid: 461646]
  170. Trifolium alpestre [ncbi taxid: 97007]
  171. Trifolium apertum [ncbi taxid: 361886]
  172. Trifolium canescens [ncbi taxid: 361901]
  173. Trifolium caucasicum [ncbi taxid: 200955]
  174. Trifolium incarnatum [ncbi taxid: 60916]
  175. Trifolium medium [ncbi taxid: 97028]
  176. Trifolium pannonicum [ncbi taxid: 97032]
  177. Trifolium pratense [ncbi taxid: 57577]
  178. Trifolium pratense L. [ncbi taxid: ]
  179. Trifolium repens [ncbi taxid: 3899]
  180. Trifolium repens L. [ncbi taxid: ]
  181. Trifolium repensl [ncbi taxid: ]
  182. Trifolium subterraneum [ncbi taxid: 3900]
  183. Trifolium trichocephalum [ncbi taxid: 361995]
  184. Trigonella foenum-graecum [ncbi taxid: 78534]
  185. Trollius europaeus [ncbi taxid: 212754]
  186. Vellozia nanuzae [ncbi taxid: 3373677]
  187. Vernonia fagifolia [ncbi taxid: ]
  188. Virola caducifolia [ncbi taxid: ]
  189. Virola cadudifolia [ncbi taxid: ]
  190. Virola surinamensis [ncbi taxid: 224910]
  191. Vitex negundo [ncbi taxid: 361442]
  192. Wisteria brachybotrys [ncbi taxid: 185975]

Pathway Synthetic

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