1.0 2010-04-08 22:09:45 UTC 2019-11-26 03:05:13 UTC FDB011663 Coumestrol 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. 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 C15H8O5 268.224 268.037173358 5,14-dihydroxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-9-one coumestrol 479-13-0 OC1=CC2=C(C=C1)C1=C(O2)C2=C(OC1=O)C=C(O)C=C2 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 ZZIALNLLNHEQPJ-UHFFFAOYSA-N belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. Coumestans Organic compounds Phenylpropanoids and polyketides Isoflavonoids Coumestans Aromatic heteropolycyclic compounds 1-benzopyrans 1-hydroxy-2-unsubstituted benzenoids Angular furanocoumarins Benzofurans Furans Furopyrans Heteroaromatic compounds Hydrocarbon derivatives Lactones Organic oxides Organooxygen compounds Oxacyclic compounds Pyranones and derivatives 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid Angular furanocoumarin Aromatic heteropolycyclic compound Benzenoid Benzofuran Benzopyran Coumarin Coumestan Furan Furanocoumarin Furopyran Heteroaromatic compound Hydrocarbon derivative Lactone Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Pyran Pyranone Coumestan flavonoids Coumestan flavonoids Coumestanes an isoflavone coumestans delta-lactone polyphenol Solid logp 2.43 ALOGPS logs -2.98 ALOGPS solubility 2.81e-01 g/l ALOGPS melting_point Mp 385° logp 2.4 ChemAxon pka_strongest_acidic 7.11 ChemAxon pka_strongest_basic -3.1 ChemAxon iupac 5,14-dihydroxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-9-one ChemAxon average_mass 268.224 ChemAxon mono_mass 268.037173358 ChemAxon smiles OC1=CC2=C(C=C1)C1=C(O2)C2=C(OC1=O)C=C(O)C=C2 ChemAxon formula C15H8O5 ChemAxon 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 ChemAxon inchikey ZZIALNLLNHEQPJ-UHFFFAOYSA-N ChemAxon polar_surface_area 79.9 ChemAxon refractivity 69.62 ChemAxon polarizability 26.41 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 5549 Specdb::CMs 38365 Specdb::CMs 146684 Specdb::MsMs 81933 Specdb::MsMs 81934 Specdb::MsMs 81935 Specdb::MsMs 143163 Specdb::MsMs 143164 Specdb::MsMs 143165 Specdb::MsMs 285843 Specdb::MsMs 285844 Specdb::MsMs 285845 Specdb::MsMs 285846 Specdb::MsMs 285847 Specdb::MsMs 285848 Specdb::MsMs 373737 Specdb::MsMs 373738 Specdb::MsMs 373739 Specdb::MsMs 373740 Specdb::MsMs 373741 Specdb::MsMs 373742 Specdb::MsMs 374885 Specdb::MsMs 439961 Specdb::MsMs 440250 Specdb::MsMs 440251 Specdb::MsMs 440252 Specdb::MsMs 440253 Specdb::MsMs 440254 HMDB02326 CUE #<Reference:0x000055ce33116460> #<Reference:0x000055ce33116190> Black-eyed pea Type 1 specific Vigna unguiculata ssp. unguiculata 3920 Brassicas Unknown generic 3705 Broad bean Type 1 specific Vicia faba 3906 Brussel sprouts Type 1 specific Brassica oleracea var. gemmifera 178616 40.0 40.0 40.0 mg/100 g Common bean Type 1 specific Phaseolus vulgaris 3885 Common pea Type 1 specific Pisum sativum 3888 15.03 30.0 0.06 mg/100 g Cowpea Type 1 specific Vigna unguiculata 3917 Dandelion Type 1 specific Taraxacum officinale 50225 Fruits Unknown generic Green bean Type 1 specific Phaseolus vulgaris 3885 Green vegetables Unknown generic Herbs and Spices Unknown generic Lima bean Type 1 specific Phaseolus lunatus 3884 Miso Type 2 specific 0.0024 0.0024 0.0024 mg/100 g Mung bean Type 1 specific Vigna radiata 157791 Other soy product Type 2 specific 0.000267 0.0006 0.0 mg/100 g Pomegranate Type 1 specific Punica granatum 22663 Pulses Unknown generic Scarlet bean Type 1 specific Phaseolus coccineus 3886 Soy bean Type 1 specific Glycine max 3847 0.012367 0.037099998 0.0 mg/100 g Soy milk Type 2 specific 0.0006 0.0006 0.0006 mg/100 g Soy sauce Type 2 specific 0.0004 0.0004 0.0004 mg/100 g Soy yogurt Type 2 specific 0.0005 0.0005 0.0005 mg/100 g Spinach Type 1 specific Spinacia oleracea 3562 Sunflower Type 1 specific Helianthus annuus 4232 0.0 0.0 0.0 mg/100 g Tofu Type 2 specific 0.0007 0.0007 0.0007 mg/100 g Yellow wax bean Type 1 specific Phaseolus vulgaris 3885 Yogurt Type 2 specific 0.0005 0.0005 0.0005 mg/100 g bitter Anti lipedemic 403 Anti microbial 436 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. Anti osteoporotic 495 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti-oxidant 502 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. Estrogenic 922 Fungicide 940 A substance used to destroy fungal pests. Hypocholesterolemic 1016 Nematicide 1141 A substance used to destroy pests of the phylum Nematoda (roundworms). Nematistat 1143 Peroxidase inhibitor 1208 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Pesticide 1210 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. Phytoalexin 1223 A toxin made by a plant that acts against an organism attacking it. Utero trophic 1406 Any substance introduced into a living organism with therapeutic or diagnostic purpose.