| In ZINC since | Heavy atoms | Benign functionality |
|---|---|---|
| October 14th, 2008 | 20 | Yes |
Popular Name: Genistein Genistein
Find On: PubMed — Wikipedia — Google
CAS Numbers: 446-72-0 , CAS# 446-72-0 , [446-72-0]
4 inverted exclamation marka,5,7-Trihydroxyisoflavone
4',5,7-trihydroxyisoflavone; 5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; Differenol A
446-72-0; 5,7,4'-Trihydroxyisoflavone; C06563; Genistein
4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-hydroxyphenyl)-
5,7,4'-Trihydroxyisoflavone [446-72-0]; (Genistein, 98%)
5,7,4'-trihydroxyisoflavone; CPD-3141; genistein; isoflavone
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-one
5,7-Dihydroxy-3-(4-hydroxyphenyl)-4-benzopyrone
5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
5,7-dihydroxy-3-(4-hydroxyphenyl)chromen-4-one
5-18-04-00594 (Beilstein Handbook Reference)
CHEBI:42763; CHEBI:5302; CHEBI:24204
DIHYDROXYHYDROXYPHENYLCHROMENON
ENDOCRINE DISRUPTOR (GENISTEIN) (SEE ALSO GENISTEIN (446-72-0))
GENISTEIN (ENDOCRINE DISRUPTER)
Genistein [446-72-0]; (5,7,4'-Trihydroxyisoflavone)
| Type pH range | xlogP | Des A‑Pol Apolar desolvation (kcal/mol) | Des Pol Polar desolvation (kcal/mol) | H Don H-bond donors | H Acc H-bond acceptors | Chg Net charge | tPSA (Ų) | MWT Molecular weight (g/mol) | RB Rotatable bonds | DL |
|---|---|---|---|---|---|---|---|---|---|---|
| Ref Reference (pH 7) | 2.27 | 1.08 | -13.3 | 3 | 5 | 0 | 91 | 270.24 | 1 | ↓ |
| Note Type | Comments | Provided By |
|---|---|---|
| biological_source | V. widely distributed in the Leguminosae subf. Papilionoideae but also in Podocarpus spicatus (Podocarpaceae) and Prunus spp. (Rosaceae). Also prod. by microorganisms Streptomyce | ZereneX Building Blocks |
| Molecular_Solubility | 2.344 | Bitter DB |
| mechanism | . | ZereneX Building Blocks |
| ALOGPS_SOLUBILITY | 1.23e-01 g/l | DrugBank-experimental |
| Mp [°C] | 297 - 298 | Acros Organics |
| M.P | 306C | Indofine |
| UniProt Database Links | 7OMT6_MEDSA; 7OMT8_MEDSA; 7OMT9_MEDSA; AOXA_RAT; DHRS4_BOVIN; DHRS4_HUMAN; DHRS4_MOUSE; DHRS4_PIG; DHRS4_PONAB; DHRS4_RABIT; DHRS4_RAT; GBA3_HUMAN; HGGL_SECCE; HIDH_SOYBN; HIDM_GLYEC; I4OMT_MEDTR; I7GT1_SOYBN; NOLA_BRADU; SHB_MOUSE; SOMT2_SOYBN; U73B2_ARA | ChEBI |
| Purity | 99% | APIChem |
| Purity | >98% | Fluorochem |
| mechanism | Against protein tyrosine kinases including those activated by epidermal growth factor (EGRF) and platelet derived growth factor (PDGF) receptors | IBScreen Bioactives |
| biological_use | Antioxidant | IBScreen Bioactives |
| biological_use | Claimed antineoplastic preventative activity | IBScreen Bioactives |
| Therapy | Cytotoxic inhibitor of tyrosine kinase and topoisomerase II kinase | SMDC Iconix |
| Patent Database Links | EP0827698; EP0829261; EP1038531; EP1046396; EP1166643; EP1174144; EP1232756; EP1566176; EP1634601; EP1634607; EP1656942; EP1669080; EP1767215; EP1779858; EP1806135; EP1808169; EP1808172; EP1834636; EP1842567; EP1854462; EP1878445; EP1897530; EP1897551; EP | ChEBI |
| therap | increases bone mineral density | MicroSource Spectrum |
| Notes | Inhibitor of tyrosine protein kinase | Apollo Scientific Bioactives |
| Warnings | IRRITANT | Matrix Scientific |
| Indications | natural flavonoid food suppliment | KeyOrganics Bioactives |
| APPEARANCE | Pale yellow powder | Indofine |
| mechanism | Protein kinase inhibitor | IBScreen Bioactives IBScreen Bioactives |
| S phrase | S24/25: Avoid contact with skin and eyes. | Acros Organics |
| Target | Serine/threonine-protein kinase PLK2(Q9NYY3)&G2/mitotic-specific cyclin-B1(P14635)&Telomerase protein component 1(Q99973)&Signal transducer and activator of transcription 3(P40763)&Estrogen receptor(P03372)&Estrogen receptor beta(Q92731)&Scaffold attachme | Herbal Ingredients Targets |
| biological_use | Shows insect antifeedant and weak antibacterial activity against E. coli and Xanthomonas oryzae | IBScreen Bioactives |
| SOLUBILITY | Soluble in DMSO | Indofine |
| SOLUBILITY | Soluble in DMSO and ethanol | Indofine |
| Target | Topoisomerase; EGFR | Selleck Chemicals |
| biological_use | Weak estrogen | IBScreen Bioactives IBScreen Bioactives |
| APPEARANCE | White powder | Indofine |
| M.P. | ~306-308 C (dec) | Indofine |
| MP | ~306-308o C | Indofine |
| Code | Description | Organism Class | Affinity (nM) | LE (kcal/mol/atom) | Type |
|---|---|---|---|---|---|
| AA1R-2-E | Adenosine A1 Receptor (cluster #2 Of 4), Eukaryotic | Eukaryotes | 5000 | 0.37 | Binding ≤ 10μM |
| ABCG2-1-E | ATP-binding Cassette Sub-family G Member 2 (cluster #1 Of 2), Eukaryotic | Eukaryotes | 8800 | 0.35 | Binding ≤ 10μM |
| ABL1-1-E | Tyrosine-protein Kinase ABL (cluster #1 Of 1), Eukaryotic | Eukaryotes | 10000 | 0.35 | Binding ≤ 10μM |
| AOFA-4-E | Monoamine Oxidase A (cluster #4 Of 8), Eukaryotic | Eukaryotes | 900 | 0.42 | Binding ≤ 10μM |
| AOFB-4-E | Monoamine Oxidase B (cluster #4 Of 8), Eukaryotic | Eukaryotes | 900 | 0.42 | Binding ≤ 10μM |
| DHB1-1-E | Estradiol 17-beta-dehydrogenase 1 (cluster #1 Of 1), Eukaryotic | Eukaryotes | 2210 | 0.40 | Binding ≤ 10μM |
| EGFR-2-E | Epidermal Growth Factor Receptor ErbB1 (cluster #2 Of 4), Eukaryotic | Eukaryotes | 2600 | 0.39 | Binding ≤ 10μM |
| ERR1-1-E | Estrogen-related Receptor Alpha (cluster #1 Of 1), Eukaryotic | Eukaryotes | 10 | 0.56 | Binding ≤ 10μM |
| ERR2-1-E | Estrogen-related Receptor Beta (cluster #1 Of 1), Eukaryotic | Eukaryotes | 395 | 0.45 | Binding ≤ 10μM |
| ESR1-1-E | Estrogen Receptor Alpha (cluster #1 Of 5), Eukaryotic | Eukaryotes | 990 | 0.42 | Binding ≤ 10μM |
| ESR2-4-E | Estrogen Receptor Beta (cluster #4 Of 4), Eukaryotic | Eukaryotes | 990 | 0.42 | Binding ≤ 10μM |
| MGA-3-E | Maltase-glucoamylase (cluster #3 Of 3), Eukaryotic | Eukaryotes | 2610 | 0.39 | Binding ≤ 10μM |
| Q965D7-2-E | Fatty Acid Synthase (cluster #2 Of 2), Eukaryotic | Eukaryotes | 7000 | 0.36 | Binding ≤ 10μM |
| ESR1-1-E | Estrogen Receptor Alpha (cluster #1 Of 3), Eukaryotic | Eukaryotes | 950 | 0.42 | Functional ≤ 10μM |
| ESR2-2-E | Estrogen Receptor Beta (cluster #2 Of 2), Eukaryotic | Eukaryotes | 956 | 0.42 | Functional ≤ 10μM |
| ADO-1-E | Aldehyde Oxidase (cluster #1 Of 3), Eukaryotic | Eukaryotes | 340 | 0.45 | ADME/T ≤ 10μM |
| Z50420-1-O | Trypanosoma Brucei Brucei (cluster #1 Of 7), Other | Other | 4200 | 0.38 | Functional ≤ 10μM |
| Z80030-1-O | ANN-1 (cluster #1 Of 2), Other | Other | 8000 | 0.36 | Functional ≤ 10μM |
| Z80037-1-O | Balb/MK (cluster #1 Of 1), Other | Other | 9100 | 0.35 | Functional ≤ 10μM |
| Z80224-1-O | MCF7 (Breast Carcinoma Cells) (cluster #1 Of 14), Other | Other | 1000 | 0.42 | Functional ≤ 10μM |
| Z81068-1-O | Ishikawa (Uterine Carcinoma Cells) (cluster #1 Of 1), Other | Other | 510 | 0.44 | Functional ≤ 10μM |
| Z81247-2-O | HeLa (Cervical Adenocarcinoma Cells) (cluster #2 Of 9), Other | Other | 956 | 0.42 | Functional ≤ 10μM |
| Uniprot | Swissprot | Description | Affinity (nM) | LE (kcal/mol/atom) | Type |
|---|---|---|---|---|---|
| EGFR_HUMAN | P00533 | Epidermal Growth Factor Receptor ErbB1, Human | 1000 | 0.42 | Binding ≤ 1μM |
| ESR1_HUMAN | P03372 | Estrogen Receptor Alpha, Human | 20 | 0.54 | Binding ≤ 1μM |
| ESR2_HUMAN | Q92731 | Estrogen Receptor Beta, Human | 1.3 | 0.62 | Binding ≤ 1μM |
| ERR1_HUMAN | P11474 | Estrogen-related Receptor Alpha, Human | 10 | 0.56 | Binding ≤ 1μM |
| ERR2_HUMAN | O95718 | Estrogen-related Receptor Beta, Human | 395 | 0.45 | Binding ≤ 1μM |
| AOFA_HUMAN | P21397 | Monoamine Oxidase A, Human | 900 | 0.42 | Binding ≤ 1μM |
| AOFB_HUMAN | P27338 | Monoamine Oxidase B, Human | 900 | 0.42 | Binding ≤ 1μM |
| AA1R_RAT | P25099 | Adenosine A1 Receptor, Rat | 5000 | 0.37 | Binding ≤ 10μM |
| ABCG2_HUMAN | Q9UNQ0 | ATP-binding Cassette Sub-family G Member 2, Human | 6900 | 0.36 | Binding ≤ 10μM |
| EGFR_HUMAN | P00533 | Epidermal Growth Factor Receptor ErbB1, Human | 1000 | 0.42 | Binding ≤ 10μM |
| DHB1_HUMAN | P14061 | Estradiol 17-beta-dehydrogenase 1, Human | 2210 | 0.40 | Binding ≤ 10μM |
| ESR1_HUMAN | P03372 | Estrogen Receptor Alpha, Human | 1145 | 0.42 | Binding ≤ 10μM |
| ESR2_HUMAN | Q92731 | Estrogen Receptor Beta, Human | 1.3 | 0.62 | Binding ≤ 10μM |
| ERR1_HUMAN | P11474 | Estrogen-related Receptor Alpha, Human | 10 | 0.56 | Binding ≤ 10μM |
| ERR2_HUMAN | O95718 | Estrogen-related Receptor Beta, Human | 395 | 0.45 | Binding ≤ 10μM |
| Q965D7_PLAFA | Q965D7 | Fatty Acid Synthase, Plafa | 7000 | 0.36 | Binding ≤ 10μM |
| MGA_HUMAN | O43451 | Maltase-glucoamylase, Human | 2610 | 0.39 | Binding ≤ 10μM |
| AOFA_HUMAN | P21397 | Monoamine Oxidase A, Human | 900 | 0.42 | Binding ≤ 10μM |
| AOFB_HUMAN | P27338 | Monoamine Oxidase B, Human | 900 | 0.42 | Binding ≤ 10μM |
| ABL1_HUMAN | P00519 | Tyrosine-protein Kinase ABL, Human | 10000 | 0.35 | Binding ≤ 10μM |
| Z80030 | Z80030 | ANN-1 | 8000 | 0.36 | Functional ≤ 10μM |
| Z80037 | Z80037 | Balb/MK | 9100 | 0.35 | Functional ≤ 10μM |
| ESR1_HUMAN | P03372 | Estrogen Receptor Alpha, Human | 810 | 0.43 | Functional ≤ 10μM |
| ESR2_HUMAN | Q92731 | Estrogen Receptor Beta, Human | 1.7 | 0.61 | Functional ≤ 10μM |
| Z81247 | Z81247 | HeLa (Cervical Adenocarcinoma Cells) | 73 | 0.50 | Functional ≤ 10μM |
| Z81068 | Z81068 | Ishikawa (Uterine Carcinoma Cells) | 510 | 0.44 | Functional ≤ 10μM |
| Z80224 | Z80224 | MCF7 (Breast Carcinoma Cells) | 1000 | 0.42 | Functional ≤ 10μM |
| Z50420 | Z50420 | Trypanosoma Brucei Brucei | 4200 | 0.38 | Functional ≤ 10μM |
| ADO_HUMAN | Q06278 | Aldehyde Oxidase, Human | 340 | 0.45 | ADME/T ≤ 10μM |
| Description | Species |
|---|---|
| Abacavir transmembrane transport | |
| Adenosine P1 receptors | |
| CDO in myogenesis | |
| Constitutive PI3K/AKT Signaling in Cancer | |
| Digestion of dietary carbohydrate | |
| EGFR downregulation | |
| EGFR interacts with phospholipase C-gamma | |
| EGFR Transactivation by Gastrin | |
| Enzymatic degradation of dopamine by COMT | |
| Enzymatic degradation of Dopamine by monoamine oxidase | |
| Estrogen biosynthesis | |
| Factors involved in megakaryocyte development and platelet production | |
| G alpha (i) signalling events | |
| GAB1 signalosome | |
| GRB2 events in EGFR signaling | |
| GRB2 events in ERBB2 signaling | |
| Iron uptake and transport | |
| Metabolism of serotonin | |
| Monoamines are oxidized to aldehydes by MAOA and MAOB, producing NH3 and H2O2 | |
| Norepinephrine Neurotransmitter Release Cycle | |
| Nuclear Receptor transcription pathway | |
| Nuclear signaling by ERBB4 | |
| PI3K events in ERBB2 signaling | |
| PIP3 activates AKT signaling | |
| PLCG1 events in ERBB2 signaling | |
| PPARA activates gene expression | |
| Regulation of actin dynamics for phagocytic cup formation | |
| Role of Abl in Robo-Slit signaling | |
| SHC1 events in EGFR signaling | |
| SHC1 events in ERBB2 signaling | |
| Signal transduction by L1 | |
| Signaling by constitutively active EGFR | |
| Signaling by EGFR | |
| Signaling by ERBB2 | |
| Signaling by ERBB4 | |
| The canonical retinoid cycle in rods (twilight vision) | |
| Transcriptional activation of mitochondrial biogenesis | |
| Vitamins B6 activation to pyridoxal phosphate |
