Coumestrol (BioCAD00000008934)

blood urine

Metabolite Card

Formula: C15H8O5 (268.0372)
SMILES: OC1=CC2=C(C=C1)C1=C(O2)C2=C(OC1=O)C=C(O)C=C2

Synonyms [en]

Coumestrol; 3,9-Dihydroxycoumestan; Coumesterol; 3,9-Dihydroxy-6H-[1]benzofuro[3,2-c]chromen-6-one; V7NW98OB34; SMP2_000163

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Coumestrol. 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: BioCAD00000008934). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Cumoesterol (or 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).

Membrane
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 479-13-0
  • CAS Registry Number: 6561-60-0
  • PubChem: 5281707
  • ChEBI: ChEBI:3908
  • HMDB: HMDB0002326
  • LipidMaps: LMPK12090018
  • KEGG: C10205
  • BioCyc: CPD-11779
  • NCBI MeSH: Coumestrol
  • Wikipedia: Coumestrol
  • RefMet: RM0128448
  • MoNA: HMDB0002326_ms_ms_285843
  • MoNA: HMDB0002326_ms_ms_285844
  • MoNA: HMDB0002326_ms_ms_285845
  • MoNA: HMDB0002326_ms_ms_285846
  • MoNA: HMDB0002326_ms_ms_285847
  • MoNA: HMDB0002326_ms_ms_285848
  • MoNA: MetaboBASE0252
  • MoNA: MetaboBASE0253
  • MoNA: MetaboBASE0254
  • MoNA: MetaboBASE0255
  • MoNA: MetaboBASE0256
  • MoNA: MetaboBASE0257
  • MoNA: VF-NPL-LTQ000455
  • MoNA: VF-NPL-LTQ000456
  • Metlin: METLIN_48332
  • Coconut NaturalProduct: CNP0328371.0
  • Coconut NaturalProduct: CNP0345258.0
  • Coconut NaturalProduct: CNP0598708.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R07726 C10200<=>C10205
BioCyc:RXN-11643 CPD-11782 --> CPD-11779
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Organism Source

Taxonomy Source

  1. Beilschmiedia fulva [ncbi taxid: ]
  2. Bituminaria morisiana [ncbi taxid: ]
  3. Brassica oleracea [ncbi taxid: 3712]
  4. Cullen corylifolium [ncbi taxid: 429560]
  5. Dolichos biflorus [ncbi taxid: ]
  6. ducrosia ismaelis [ncbi taxid: ]
  7. Elettaria cardamomum [ncbi taxid: 105181]
  8. Glycine canescens [ncbi taxid: 48924]
  9. Glycine clandestina [ncbi taxid: 45687]
  10. Glycine falcata [ncbi taxid: 45690]
  11. Glycine latifolia [ncbi taxid: 45691]
  12. Glycine max [ncbi taxid: 3847]
  13. Glycine max (L.) Merr. [ncbi taxid: ]
  14. Glycine tabacina [ncbi taxid: 44016]
  15. Glycine tomentella [ncbi taxid: 44015]
  16. Hedysarum polybotrys [ncbi taxid: 119828]
  17. Homo sapiens [ncbi taxid: 9606]
  18. Medicago sativa [ncbi taxid: 3879]
  19. Medicago spp. [ncbi taxid: ]
  20. Melilotus alba [ncbi taxid: ]
  21. Melilotus messanensis [ncbi taxid: 1279044]
  22. Phaseolus coccineus [ncbi taxid: 3886]
  23. Phaseolus lunatus [ncbi taxid: 3884]
  24. Phaseolus spp. [ncbi taxid: ]
  25. Phaseolus vulgaris [ncbi taxid: 3885]
  26. Pisum sativum [ncbi taxid: ]
  27. Pueraria lobata [ncbi taxid: ]
  28. Pueraria mirifica [ncbi taxid: ]
  29. Pueraria montana [ncbi taxid: 132459]
  30. Pueraria montana var. lobata [ncbi taxid: 3893]
  31. Punica granatum [ncbi taxid: 22663]
  32. Spinacia oleracea [ncbi taxid: 3562]
  33. Tacca leontopetaloides [ncbi taxid: 72648]
  34. Taraxacum officinale [ncbi taxid: 50225]
  35. Teucrium polium [ncbi taxid: 1117157]
  36. Trifolium fragiferum [ncbi taxid: 97023]
  37. Trifolium pratense [ncbi taxid: 57577]
  38. Trifolium pratense L. [ncbi taxid: ]
  39. Trifolium repens [ncbi taxid: 3899]
  40. Trifolium repens L. [ncbi taxid: ]
  41. Trifolium subterraneum [ncbi taxid: 3900]
  42. Vigna radiata [ncbi taxid: 157791]
  43. Vigna unguiculata [ncbi taxid: 3917]
  44. Ziziphus jujuba [ncbi taxid: 326968]
  45. Ziziphus jujuba var. spinosa [ncbi taxid: 714518]

Pathway Synthetic

pathway id name
BioCyc:META_PWY-2002 isoflavonoid biosynthesis I
BioCyc:META_PWY-6332 coumestrol biosynthesis
PlantCyc:PLANT_PWY-6332 coumestrol biosynthesis
View All Pathways