Compound: genistein
SMILES: O=c1c2c(occ1-c3ccc(O)cc3)cc(O)cc2O
InChIKey: TZBJGXHYKVUXJN-UHFFFAOYSA-N
Synonyms: genistein, 446-72-0, Prunetol, 4',5,7-Trihydroxyisoflavone, Genisterin, Genisteol, Sophoricol, 5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one, 5,7-dihydroxy-3-(4-hydroxyphenyl)chromen-4-one, 5,7,4'-Trihydroxyisoflavone, Bonistein, Genestein, 4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-hydroxyphenyl)-, 5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, 4',5, 7-Trihydroxyisoflavone, DTXSID5022308, NSC36586, NSC-36586, DH2M523P0H, NPI-031L, CHEBI:28088, BIO-300, SIPI-807-1, FW-635I-2, DTXCID002308, 5,7-dihydroxy-3-(4-hydroxyphenyl)-chromen-4-one, RefChem:5853, TEMPO HOT FLASH RELIEF, alpha-ISOSPARTEINE, (-)-, SPARTEINE L-alpha-ISOSPARTEINE, 207-174-9, NSC-366737, Differenol A, NPI 031L, MFCD00016952, C.I. 75610, SIPI 807-1, NSC 36586, Genistein [USAN], 5,7-Dihydroxy-3-(4-hydroxyphenyl)-4-benzopyrone, Genistein (Standard), CHEMBL44, Bio 300, ISOFLAVONE, 4',5,7-TRIHYDROXY-, MLS000738127, Genistein (USAN), s1342, GEN, NCGC00015479-09, 690224-00-1, CAS-446-72-0, Lactoferrin-genistein, CCRIS 7675, 1x7r, SR-01000075498, EINECS 207-174-9, BRN 0263823, UNII-DH2M523P0H, Genisteina, Genistein?, STO514, 4',5,7-Trihydroxy isoflavone, HSDB 7475, PTI G4660, PTI-G4660, SIPI-9764-I, AgeGuard GN, 3kgt, 3kgu, Genistein, 8, PTI-G 4660, Genistein (GEN), TNP00151, Spectrum_000320, Tocris-1110, 2qa8, Genistein 85% HPLC, GENISTEIN [INN], SpecPlus_000305, GENISTEIN [MI], GENISTEIN [HSDB], Spectrum2_000638, Spectrum3_000678, Spectrum4_001543, Spectrum5_000106, Lopac-G-6649, 4',7-Trihydroxyisoflavone, Epitope ID:613462, GENISTEIN [MART.], MolMap_000022, UPCMLD-DP096, G 6649, G10000, GENISTEIN [USP-RS], GENISTEIN [WHO-DD], Isoflavone,5,7-trihydroxy-, Lopac0_000520, Oprea1_224620, Oprea1_437815, SCHEMBL19166, BSPBio_002375, KBioGR_002006, KBioGR_002564, KBioSS_000800, KBioSS_002573, NPI031L, SPECTRUM210296, 5-18-04-00594 (Beilstein Handbook Reference), BIDD:ER0113, DivK1c_006401, Genistein, analytical standard, SPBio_000636, 4',5,7-.Trihydroxyisoflavone, 4',5,7-trihydroxy-Isoflavone, GTPL2826, MEGxp0_000568, orb1307572, orb3025503, 4,5,7-Trihydroxy Iso-Flavone, SCHEMBL29352944, UPCMLD-DP096:001, ACon1_001065, BDBM19459, cid_5280961, KBio1_001345, KBio2_000800, KBio2_002564, KBio2_003368, KBio2_005132, KBio2_005936, KBio2_007700, KBio3_001595, KBio3_003042, CHEBI: 28088, cMAP_000086, Bio1_000445, Bio1_000934, Bio1_001423, GLXC-06701, HMS2271K09, HMS3261H21, HMS3267K14, HMS3412I13, HMS3428M01, HMS3649B22, HMS3654D17, HMS3676I13, HMS3742I07, HMS5079F13, ALBB-015886, MSK40142, Tox21_110161, Tox21_201428, Tox21_300585, Tox21_500520, 5,7,4'-trihydroxy dihydroisoflavone, AC-472, BBL010484, CCG-38551, EBC-11079, HB2775, HY-14596R, LMPK12050218, SBB066115, STK801619, WHO 11073, AKOS001590147, Tox21_110161_1, CS-1534, DB01645, FG09961, KS-5128, LP00520, SB17235, SDCCGSBI-0050503.P003, SMP1_000133, Genistein; 4',5,7-Trihydroxyisoflavone, NCGC00015479-01, NCGC00015479-02, NCGC00015479-04, NCGC00015479-05, NCGC00015479-06, NCGC00015479-07, NCGC00015479-08, NCGC00015479-10, NCGC00015479-11, NCGC00015479-12, NCGC00015479-13, NCGC00015479-14, NCGC00015479-15, NCGC00015479-16, NCGC00015479-17, NCGC00015479-18, NCGC00015479-19, NCGC00015479-20, NCGC00015479-38, NCGC00025005-01, NCGC00025005-02, NCGC00025005-03, NCGC00025005-04, NCGC00025005-05, NCGC00025005-06, NCGC00025005-07, NCGC00169711-01, NCGC00169711-02, NCGC00254275-01, NCGC00258979-01, NCGC00261205-01, HY-14596, NCI60_003369, SMR000112580, ST056352, SY050124, CS-0694819, EU-0100520, G0272, NS00009870, SW203763-2, C06563, D11680, EN300-210743, G-2535, Genistein, synthetic, >=98% (HPLC), powder, K00046, M01798, US8552057, 2, AB00052696_09, AB00052696_12, AE-848/20772043, Q415957, GENISTEIN (CONSTITUENT OF RED CLOVER) [DSC], Genistein, primary pharmaceutical reference standard, SR-01000075498-1, SR-01000075498-3, SR-01000075498-6, BRD-K43797669-001-02-3, BRD-K43797669-001-03-1, BRD-K43797669-001-10-6, BRD-K43797669-001-28-8, BRD-K43797669-001-29-6, BRD-K43797669-001-30-4, Genistein, from Glycine max (soybean), ~98% (HPLC), SR-01000075498-10, F0001-2388, GENISTEIN (CONSTITUENT OF SOY ISOFLAVONES) [DSC], 4H-1-Benzopyran-4-one,7-dihydroxy-3-(4-hydroxyphenyl)-, Genistein, United States Pharmacopeia (USP) Reference Standard, Genistein, Pharmaceutical Secondary Standard; Certified Reference Material
Theoretical properties:
molecular_formula: C15H10O5
molecular_weight: 270.24 g/mol
exact_mass: 270.05282342 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 1
heavy_atom_count: 20
topological_polar_surface_area: 87 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Rectangular or six-sided rods from 60% alcohol. Dendritic needles from ether
color: Rectangular or six-sided rods from 60% alcohol. Dendritic needles from ether
solubility: Soluble in the usual organic solvents; soluble in dilute alkalies with yellow color. Practically insoluble in water.
Descriptions:
pubchem: Genistein is a 7-hydroxyisoflavone with additional hydroxy groups at positions 5 and 4'. It is a phytoestrogenic isoflavone with antioxidant properties. It has a role as a geroprotector, an antineoplastic agent, a tyrosine kinase inhibitor, an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor, a plant metabolite, a phytoestrogen and a human urinary metabolite. It is a conjugate acid of a genistein(1-).
chebi: A 7-hydroxyisoflavone with additional hydroxy groups at positions 5 and 4'. It is a phytoestrogenic isoflavone with antioxidant properties.
chembl: GENISTEIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: Genistein (C15H10O5) is a plant-derived, aglycone isoflavone. Genistein has the highest content of all isoflavones in soybeans and soy products, such as tempeh. As a type of phytoestrogen, genistein is classed as an endocrine disrupting chemical due to its estrogenic activity in vitro and in vivo. Consequently, excessive consumption of soy products has been linked to disruption of the reproductive organs, such as the uterus, breast, and testis.
It was first isolated in 1899 from the dyer's broom, Genista tinctoria; hence, the chemical name. The compound structure was established in 1926, when it was found to be identical with that of prunetol. It was chemically synthesized in 1928. Genistein is a primary secondary metabolite of the Trifolium species and Glycine max (soy).