Compound: COUMESTROL
SMILES: O=c1oc2c(ccc(c2)O)c3c1c4c(cc(O)cc4)o3
InChIKey: ZZIALNLLNHEQPJ-UHFFFAOYSA-N
Synonyms: COUMESTROL, 479-13-0, Cumoestrol, Cumostrol, 3,9-Dihydroxycoumestan, DTXSID6022399, V7NW98OB34, 3,9-dihydroxy-[1]benzofuro[3,2-c]chromen-6-one, 3,9-Dihydroxy-6H-benzofuro(3,2-c)(1)benzopyran-6-one, 6H-Benzofuro[3,2-c][1]benzopyran-6-one, 3,9-dihydroxy-, NSC-22842, CHEBI:3908, DTXCID102399, 6H-Benzofuro(3,2-c)(1)benzopyran-6-one, 3,9-dihydroxy-, 3,9-dihydroxy-(1)benzofuro(3,2-c)chromen-6-one, RefChem:33625, 207-525-6, Cumoesterol, 3,9-Dihydroxy-6H-[1]benzofuro[3,2-c]chromen-6-one, NSC 22842, Cumestrol, MFCD00016885, 3,9-dihydroxy-6H-benzofuro[3,2-c]chromen-6-one, NSC22842, CHEMBL30707, MLS000738006, 3,9-dihydroxybenzofuro[3,2-c]chromen-6-one, Coumesterol, SMR000059001, CCRIS 7311, EINECS 207-525-6, BRN 0266702, UNII-V7NW98OB34, Coumestrol?, Coumestrol (COU), Coumestrol (Standard), COUMESTROL [MI], NCIMech_000078, Oprea1_222511, SCHEMBL22012, 5-19-06-00405 (Beilstein Handbook Reference), MLS000069446, BIDD:ER0114, orb1296071, orb3140751, SCHEMBL29453366, 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, EBC-436047, FC20578, 3-Benzofurancarboxylic acid, 2-(2,4-dihydroxyphenyl)-6-hydroxy-, delta-lactone, 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, ST50320052, D85092, S00280, US8552057, 3, 3,9-dihydroxy-[1]benzoxolo[3,2-c]chromen-6-one, 3,9-dihydroxybenzo[d]chromeno[4,3-b]furan-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-, 3,9-Dihydroxy-6H-[1]benzofuro[3,2-c][1]benzopyran-6-one, 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, 5,14-dihydroxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-9-one, 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
Theoretical properties:
molecular_formula: C15H8O5
molecular_weight: 268.22 g/mol
exact_mass: 268.03717335 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 0
heavy_atom_count: 20
topological_polar_surface_area: 79.9 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 385 °C
Descriptions:
{"pubchem": "Coumestrol is a member of the class of coumestans that is coumestan with hydroxy substituents at positions 3 and 9. It has a role as an antioxidant, an anti-inflammatory agent and a plant metabolite. It is a delta-lactone, a polyphenol and a member of coumestans. It is functionally related to a coumestan.", "chebi": "A member of the class of coumestans that is coumestan with hydroxy substituents at positions 3 and 9.", "chembl": "COUMESTROL is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "Coumestrol is a natural organic compound in the class of phytochemicals known as coumestans. Coumestrol was first identified as a compound with estrogenic properties by E. M. Bickoff in ladino clover and alfalfa in 1957.  It has garnered research interest because of its estrogenic activity and prevalence in some foods, including soybeans, brussels sprouts, spinach and a variety of legumes. The highest concentrations of coumestrol are found in clover, Kala Chana (a type of chick pea), and Alfalfa sprouts.\nCoumestrol is a phytoestrogen, mimicking the biological activity of estrogens. Phytoestrogens are able to pass through cell membranes due to their low molecular weight and stable structure, and they are able to interact with the enzymes and receptors of cells. Coumestrol binds to the ER\u03b1 and ER\u03b2 with similar affinity to that of estradiol (94% and 185% of the relative binding affinity of estradiol at the ER\u03b1 and ER\u03b2, respectively), although the estrogenic activity of coumestrol at both receptors is much less than that of estradiol. In any case, coumestrol has estrogenic activity that is 30 to 100 times greater than that of isoflavones.\nThe 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 3\u03b1-hydroxysteroid dehydrogenase. These enzymes are involved in the biosynthesis of steroid hormones, and inhibition of these enzymes results in interference with hormone metabolism."}