Coumestrol
PubChem CID: 5281707
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| Compound Synonyms | COUMESTROL, 479-13-0, Cumoestrol, Cumoesterol, Cumostrol, 3,9-Dihydroxy-6H-[1]benzofuro[3,2-c]chromen-6-one, 3,9-Dihydroxycoumestan, 7,12-Dihydroxycoumestan, NSC 22842, CCRIS 7311, Cumestrol, EINECS 207-525-6, UNII-V7NW98OB34, BRN 0266702, CHEBI:3908, V7NW98OB34, 3,9-dihydroxy-6H-benzofuro[3,2-c]chromen-6-one, 3,9-dihydroxy-[1]benzofuro[3,2-c]chromen-6-one, DTXSID6022399, NSC22842, 6H-Benzofuro[3,2-c][1]benzopyran-6-one, 3,9-dihydroxy-, MFCD00016885, NSC-22842, CHEMBL30707, 3,9-Dihydroxy-6H-benzofuro(3,2-c)(1)benzopyran-6-one, MLS000738006, DTXCID102399, 5-19-06-00405 (Beilstein Handbook Reference), 6H-Benzofuro(3,2-c)(1)benzopyran-6-one, 3,9-dihydroxy-, 3-Benzofurancarboxylic acid, 2-(2,4-dihydroxyphenyl)-6-hydroxy-, delta-lactone, Coumesterol, SMR000059001, 3,9-dihydroxy-6H-(1)benzofuro(3,2-c)chromen-6-one, Coumestrol?, Coumestrol (COU), Coumestrol (Standard), COUMESTROL [MI], 3,9-dihydroxybenzofuro[3,2-c]chromen-6-one, NCIMech_000078, Oprea1_222511, SCHEMBL22012, MLS000069446, BIDD:ER0114, BDBM23451, GTPL12437, HY-N2335R, HMS2235B05, HMS3374A07, 6H-Benzofuro[3, 3,9-dihydroxy-, Coumestrol, >=95.0% (HPLC), HY-N2335, Tox21_200032, CCG-35536, CCG-36200, LMPK12090018, MSK159856, AKOS028111776, CS-6343, FC20578, SMP2_000163, NCGC00018124-01, NCGC00018124-02, NCGC00018124-03, NCGC00018124-04, NCGC00018124-05, NCGC00018124-06, NCGC00023462-03, NCGC00023462-04, NCGC00257586-01, AS-81377, CAS-479-13-0, NCI60_001863, DB-051484, NS00004410, D85092, S00280, US8552057, 3, 3,9-dihydroxy-[1]benzoxolo[3,2-c]chromen-6-one, Q908865, A1-00298, BRD-K97509413-001-01-8, 3,9-Dihydroxy-6H-[1]benzofuro[3,2-c]chromen-6-one #, 6H-Benzofuro(3,2-c)(1)benzopyran-6-one, 3,9-dihdyroxy-, Coumestrol, BioReagent, suitable for fluorescence, >=97.5% (HPLC), 3-Benzofurancarboxylic acid,4-dihydroxyphenyl)-6-hydroxy-, .delta.-lactone, 3-Benzofurancarboxylic acid, 2-(2,4-dihydroxyphenyl)-6-hydroxy-, .delta.-lactone, CoumestrolCumoesterol, Cumostrol, 3,9-Dihydroxy-6H-[1]benzofuro[3,2-c]chromen-6-one, 207-525-6, 5,14-dihydroxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one |
|---|---|
| Ghose Rule | True |
| Classyfire Kingdom | Organic compounds |
| Topological Polar Surface Area | 79.9 |
| Hydrogen Bond Donor Count | 2.0 |
| Pfizer 3 75 Rule | False |
| Scaffold Graph Level | CC1CC2CCCCC2C2CC3CCCCC3C12 |
| Np Classifier Class | Coumestan |
| Deep Smiles | Occcccc6)oc=O)cc6occ5cccc6)O |
| Heavy Atom Count | 20.0 |
| Classyfire Class | Isoflavonoids |
| 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. |
| Scaffold Graph Node Level | OC1OC2CCCCC2C2OC3CCCCC3C12 |
| Classyfire Subclass | Coumestans |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 411.0 |
| Database Name | cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;imppat_phytochem;npass_chem_all;pubchem |
| Defined Atom Stereocenter Count | 0.0 |
| Uniprot Id | P22309, P03372, Q92731, P15207, P56937, P02545, P10828, P46063, B2RXH2, Q9NUW8, P10636, Q16665, P00352, P10253, P02791, Q03164, P00811, P15428, P06280, P54132, P06746, Q96QE3, P19793, P10275, P39748, Q9UNA4, Q9Y253, Q9UBT6, Q03181, P08659, P11473, O89049, P19838, O75496, P35869, Q16236, Q9H0H5, P17405, P63165, O94925, Q14191, Q13526, O94956, Q9NPD5, Q9Y6L6, O42275, P81908, O94782, P53350, P27695, O75469, n.a., P68400, Q8NEV1, P04792 |
| Iupac Name | 3,9-dihydroxy-[1]benzofuro[3,2-c]chromen-6-one |
| Prediction Hob | 1.0 |
| Class | Isoflavonoids |
| Veber Rule | True |
| Classyfire Superclass | Phenylpropanoids and polyketides |
| Target Id | NPT108, NPT248, NPT483, NPT46, NPT47, NPT48, NPT50, NPT51, NPT211, NPT94, NPT60, NPT151, NPT501, NPT58, NPT59, NPT543, NPT1598 |
| Xlogp | 2.8 |
| Superclass | Phenylpropanoids and polyketides |
| Subclass | Coumestans |
| Gsk 4 400 Rule | True |
| Molecular Formula | C15H8O5 |
| Scaffold Graph Node Bond Level | O=c1oc2ccccc2c2oc3ccccc3c12 |
| Prediction Swissadme | 0.0 |
| Inchi Key | ZZIALNLLNHEQPJ-UHFFFAOYSA-N |
| Silicos It Class | Moderately soluble |
| Fcsp3 | 0.0 |
| Logs | -4.123 |
| Rotatable Bond Count | 0.0 |
| State | Solid |
| Logd | 2.908 |
| Synonyms | 3,9-Dihydroxy-6-oxopterocarpen (obsol.), 3,9-Dihydroxy-6H-[1]benzofuro[3,2-c]chromen-6-one, 3,9-Dihydroxy-6H-benzofuro(3,2-c)(1)benzopyran-6-one, 3,9-Dihydroxy-6H-benzofuro[3,2-c][1]benzopyran-6-one, 9CI, 3,9-Dihydroxycoumestan, 6',7-Dihydroxybenzofuro[3',2',3,4]coumarin (obsol.), 6H-Benzofuro(3,2-c)(1)benzopyran-6-one, 3,9-dihydroxy-, 6H-Benzofuro[3,2-c][1]benzopyran-6-one, 3,9-dihydroxy-, 7,12-Dihydroxycoumestan, 7,12-Dihydroxycoumestan (obsol.), Chrysanthin, Cumoesterol, Cumoestrol, Cumostrol, Coumestrol, coumesterol, coumestrol, cumestrol |
| Substituent Name | Furanocoumarin, Coumestan, Angular furanocoumarin, Coumarin, 1-benzopyran, Benzopyran, Furopyran, Benzofuran, Pyranone, Benzenoid, Pyran, Heteroaromatic compound, Furan, Lactone, Oxacycle, Organoheterocyclic compound, Hydrocarbon derivative, Organooxygen compound, Aromatic heteropolycyclic compound |
| Esol Class | Soluble |
| Functional Groups | c=O, cO, coc |
| Compound Name | Coumestrol |
| Kingdom | Organic compounds |
| Prediction Hob Swissadme | 0.0 |
| Exact Mass | 268.037 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 268.037 |
| Hydrogen Bond Acceptor Count | 5.0 |
| Molecular Weight | 268.22 |
| Gi Absorption | True |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 0.0 |
| Total Bond Stereocenter Count | 0.0 |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Lipinski Rule Of 5 | True |
| Esol | -4.1731888 |
| Inchi | 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 |
| Smiles | C1=CC2=C(C=C1O)OC3=C2C(=O)OC4=C3C=CC(=C4)O |
| Nring | 4.0 |
| Np Classifier Biosynthetic Pathway | Shikimates and Phenylpropanoids |
| Defined Bond Stereocenter Count | 0.0 |
| Egan Rule | True |
| Taxonomy Direct Parent | Coumestans |
| Np Classifier Superclass | Isoflavonoids |
- 1. Outgoing r'ship
FOUND_INto/from Anacyclus Pyrethrum (Plant) Rel Props:Reference:ISBN:9770972795006 - 2. Outgoing r'ship
FOUND_INto/from Brassica Oleracea (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all;npass_chem_all - 3. Outgoing r'ship
FOUND_INto/from Cullen Corylifolium (Plant) Rel Props:Reference:ISBN:9780387706375; ISBN:9788185042114 - 4. Outgoing r'ship
FOUND_INto/from Elettaria Cardamomum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 5. Outgoing r'ship
FOUND_INto/from Glycine Max (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all;npass_chem_all - 6. Outgoing r'ship
FOUND_INto/from Hedysarum Polybotrys (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 7. Outgoing r'ship
FOUND_INto/from Lepidium Sativum (Plant) Rel Props:Reference:ISBN:9770972795006 - 8. Outgoing r'ship
FOUND_INto/from Macrotyloma Uniflorum (Plant) Rel Props:Reference:ISBN:9788172360481 - 9. Outgoing r'ship
FOUND_INto/from Medicago Sativa (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 10. Outgoing r'ship
FOUND_INto/from Phaseolus Coccineus (Plant) Rel Props:Source_db:fooddb_chem_all - 11. Outgoing r'ship
FOUND_INto/from Phaseolus Lunatus (Plant) Rel Props:Source_db:fooddb_chem_all - 12. Outgoing r'ship
FOUND_INto/from Phaseolus Vulgaris (Plant) Rel Props:Source_db:fooddb_chem_all - 13. Outgoing r'ship
FOUND_INto/from Pisum Sativum (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all;npass_chem_all - 14. Outgoing r'ship
FOUND_INto/from Pueraria Lobata (Plant) Rel Props:Source_db:npass_chem_all - 15. Outgoing r'ship
FOUND_INto/from Pueraria Montana (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 16. Outgoing r'ship
FOUND_INto/from Punica Granatum (Plant) Rel Props:Source_db:fooddb_chem_all - 17. Outgoing r'ship
FOUND_INto/from Sphagneticola Calendulacea (Plant) Rel Props:Reference:ISBN:9780387706375 - 18. Outgoing r'ship
FOUND_INto/from Spinacia Oleracea (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all;npass_chem_all - 19. Outgoing r'ship
FOUND_INto/from Tacca Leontopetaloides (Plant) Rel Props:Source_db:npass_chem_all - 20. Outgoing r'ship
FOUND_INto/from Taraxacum Officinale (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all;npass_chem_all - 21. Outgoing r'ship
FOUND_INto/from Teucrium Polium (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 22. Outgoing r'ship
FOUND_INto/from Trifolium Fragiferum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 23. Outgoing r'ship
FOUND_INto/from Trifolium Pratense (Plant) Rel Props:Reference:ISBN:9788185042084 - 24. Outgoing r'ship
FOUND_INto/from Trifolium Repens (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 25. Outgoing r'ship
FOUND_INto/from Vicia Faba (Plant) Rel Props:Source_db:fooddb_chem_all - 26. Outgoing r'ship
FOUND_INto/from Vigna Radiata (Plant) Rel Props:Source_db:fooddb_chem_all - 27. Outgoing r'ship
FOUND_INto/from Vigna Unguiculata (Plant) Rel Props:Source_db:fooddb_chem_all - 28. Outgoing r'ship
FOUND_INto/from Ziziphus Jujuba (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all