5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one

• ChemBase ID: 1421
• Molecular Formular: C15H10O5
• Molecular Mass: 270.2369
• Monoisotopic Mass: 270.05282342
• SMILES: c1c(O)cc(O)c2c(=O)c(coc12)c1ccc(O)cc1
• Canonical SMILES: Oc1ccc(cc1)c1coc2c(c1=O)c(O)cc(c2)O
• InChI: InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H
• InChIKey: TZBJGXHYKVUXJN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
• IUPAC Traditional name: genistein; 5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
• Brand Name: Prunetol; Sophoricol
• Synonyms: Genistein; 4',5,7-Trihydroxyisoflavone; Baichanin A; Bonistein; GeniVida; NSC 36586; Prunetol; Sophoricol; 4',5, 7-Trihydroxyisoflavone; 5,7,4'-Trihydroxyisoflavone; Genisteol; Genisterin; Genistein; 5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one; 4′,5,7-Trihydroxyisoflavone; Genistein; 4',5,7-Trihydroxyisoflavone; 4,5,7-Trihydroxyiso-flavone; 5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 4',5,7-三羟基异黄酮

Database IDs

• CAS Number: 446-72-0
• EC Number: 207-174-9
• MDL Number: MFCD00016952
• Beilstein Number: 263823
• Merck Index: 144391
• PubChem SID: 24278036; 46509060; 24895273; 160964881
• PubChem CID: 5280961
• CHEBI ID: 28088
• CHEMBL: 44
• Chemspider ID: 4444448
• DrugBank ID: DB01645
• KEGG ID: C06563
• Unique Ingredient Identifier: DH2M523P0H
• Wikipedia Title: Genistein

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.54627
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 3.0396812
• LogD (pH = 7.4): 2.1150076
• Log P: 3.0768723
• Molar Refractivity: 71.6829 cm^3
• Polarizability: 27.108362 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.04
• LOG S: -3.34
• Solubility (Water): 1.23e-01 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: soluble; ethanol: soluble; Methanol
• Apperance: off-white powder; Powder; Tan to Light Yellow Solid
• Melting Point: 297-298°C; 298-300°C (dec.); ca 300°C

Safety Information

• Storage Condition: 0°C; -20°C; -20°C Freezer
• Storage Warning: IRRITANT
• RTECS: NR2392000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• TSCA Listed: false; 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Pharmacology Properties

• Target: EGFR EGFR
• Gene Information: human ... AKT1(207), CYP19A1(1588), EGFR(1956), ESR1(2099), ESR2(2100)mouse ... Esr1(13982), Hexa(15211)rat ... Adora1(29290), Adora2a(25369), Ar(24208)
• Mechanism of Action: Against protein tyrosine kinases including those activated by epidermal growth factor (EGRF) and platelet derived growth factor (PDGF) receptors; Antioxidant; Protein kinase inhibitor

Product Information

• Purity: ~98% (HPLC); ≥97% (HPLC); ≥98% (HPLC); 97%; 98.5
• Grade: analytical standard
• Salt Data: Free Base
• Biological Source: from Glycine max (soybean); synthetic; V. widely distributed in the Leguminosae subf. Papilionoideae but also in Podocarpus spicatus (Podocarpaceae) and Prunus spp. (Rosaceae). Also prod. by microorganisms Streptomyces vulgare and other Streptomyces spp., Aspergillus niger, Mycobacterium phlei and Micromonospora halophytica. The major isoflavone in soy beans and isolated soy protein
• Shelf Life: (limited shelf life, expiry date on the label)
• Application(s): Antioxidant; Claimed antineoplastic preventative activity; Shows insect antifeedant and weak antibacterial activity against E. coli and Xanthomonas oryzae; Weak estrogen
• Empirical Formula (Hill Notation): C15H10O5

DETAILS

MP Biomedicals - 02152355

Highly specific inhibitor of tyrosine protein kinases. Also inhibits EGF-stimulated phosphorylation in cultured cells. Genistein is an isoflavone compound isolated from the fermentation broth of Pseudomonas sp.

DrugBank - DB01645

• Drug Groups: experimental
• Description: An isoflavonoid derived from soy products. It inhibits protein-tyrosine kinase and topoisomerase-II (DNA topoisomerases, type II) activity and is used as an antineoplastic and antitumor agent. Experimentally, it has been shown to induce G2 phase arrest in human and murine cell lines.
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia

Selleck Chemicals - S1342

Research Area: Prostate cancer
Biological Activity:
Genistein is a soy-derived isoflavone and phytoestrogen with antineoplastic activity. Genistein binds to and inhibits protein-tyrosine kinase, thereby disrupting signal transduction and inducing cell differentiation. This agent also inhibits topoisomerase-II, leading to DNA fragmentation and apoptosis, and induces G2/M cell cycle arrest. Genistein exhibits antioxidant, antiangiogenic, and immunosuppressive activities. [1]

Sigma Aldrich - G6649

Biochem/physiol Actions
Inhibitor of tyrosine protein kinase; competitive inhibitor of ATP in other protein kinase reactions. Antiangiogenic agent, down-regulates the transcription of genes involved in controlling angiogenesis.

Sigma Aldrich - G6776

Biochem/physiol Actions
Inhibitor of tyrosine protein kinase; competitive inhibitor of ATP in other protein kinase reactions. Antiangiogenic agent, down-regulates the transcription of genes involved in controlling angiogenesis.

Sigma Aldrich - 92136

Biochem/physiol Actions
Inhibitor of tyrosine protein kinase; competitive inhibitor of ATP in other protein kinase reactions. Antiangiogenic agent, down-regulates the transcription of genes involved in controlling angiogenesis.

Toronto Research Chemicals - G350000

Exhibits specific inhibitory activity against tyrosine kinases,including autophosphorylation of epidermal growth factor receptor kinase (IC50 - 2.6uM). Also inhibits other protein kinases through competitive inhibition of ATP. Inhibits tumor cell prolif

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