Compound: Glycitein
SMILES: O=c1c(-c2ccc(O)cc2)coc3c1cc(OC)c(c3)O
InChIKey: DXYUAIFZCFRPTH-UHFFFAOYSA-N
Synonyms: Glycitein, 40957-83-3, 7,4'-Dihydroxy-6-methoxyisoflavone, 4H-1-Benzopyran-4-one, 7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-, 7-Hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-1-benzopyran-4-one, 7-hydroxy-3-(4-hydroxyphenyl)-6-methoxychromen-4-one, 92M5F28TVF, DTXSID40193960, CHEBI:34778, RefChem:143895, DTXCID80116451, 6-methoxy-7,4'-dihydroxyisoflavone, 7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-chromen-4-one, 4',7-Dihydroxy-6-methoxyisoflavone, MFCD00016679, CHEMBL513024, UNII-92M5F28TVF, Gycitein, 7-Hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-1-benzopyran-4-one; 7,4'-Dihydroxy-6-methoxyisoflavone; Glycetein; Glycitein; Glycitin aglycon, Glycitein (Standard), GLYCITEIN [USP-RS], SCHEMBL19720, BIDD:ER0470, Glycitein, analytical standard, orb1300254, orb3140037, Glycitein, >=97% (HPLC), SCHEMBL29497281, HY-N0016R, HMS3886N16, HY-N0016, MSK40160, AC-998, BDBM50241530, LMPK12050104, s9107, SBB065744, AKOS015892762, CCG-267294, EBC-615358, FG09960, AS-71538, DB-049688, NS00014840, ST50331727, Q3109347, BRD-K78303961-001-02-3, 4-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-chromen-7-one, 7-hydroxy-3-(4-hydroxyphenyl)-6-methoxychromen-4H-one, GLYCITEIN (CONSTITUENT OF SOY ISOFLAVONES) [DSC], Glycitein, United States Pharmacopeia (USP) Reference Standard
Theoretical properties:
molecular_formula: C16H12O5
molecular_weight: 284.26 g/mol
exact_mass: 284.06847348 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 2
heavy_atom_count: 21
topological_polar_surface_area: 76 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": "Glycitein is a methoxyisoflavone that is isoflavone substituted by a methoxy group at position 6 and hydroxy groups at positions 7 and 4'. It has been isolated from the mycelia of the fungus Cordyceps sinensis. It has a role as a plant metabolite, a fungal metabolite and a phytoestrogen. It is a 7-hydroxyisoflavone and a methoxyisoflavone. It is functionally related to an isoflavone.", "chebi": "A  methoxyisoflavone that is isoflavone substituted by a methoxy group at position 6 and hydroxy groups at positions 7 and 4'. It has been isolated from the mycelia of the fungus <em>Cordyceps sinensis</em>.", "chembl": "GLYCITEIN is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "Glycitein is an O-methylated isoflavone which accounts for 5-10% of the total isoflavones in soy food products. Glycitein is a phytoestrogen with weak estrogenic activity, comparable to that of the other soy isoflavones.  Like other isoflavonoids, glycitein is synthesized as a glycoside conjugate to a monosaccharide (typically glucose).  The glycoside is hydrolyzed during digestion to the biologically-active free isoflavonoid.\nGlycitein is synthesized from phenylalanine, similarly to other isoflavonoids.  The biosynthesis involves 8 steps, resulting in free glycitein; a subsequent glucosyltransferase-catalyzed reaction results in the corresponding glucoside, glycitin.  This product may be further malonylated to malonylglycitin.\nGlycitein has been investigated for its benefits to human health.  It binds to the human estrogen receptor (as do other isoflavonoids), and while it does so with lower affinity than other isoflavonoids, it is thought to be overall more potent as an estrogen receptor agonist due to its high bioavailability and its breakdown into further estrogenic products.  The estrogenic activity of glycitein is thought to underlie its suppression of oxidative stress and its promotion of decreased blood pressure, though other mechanisms are likely also involved."}