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

• ChemBase编号: 1421
• 分子式: C15H10O5
• 平均质量: 270.2369
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
• IUPAC传统名: genistein; 5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
• 商标名: Prunetol; Sophoricol
• 别名: 4',5,7-三羟基异黄酮; 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

登记号

• CAS号: 446-72-0
• EC号: 207-174-9
• MDL号: MFCD00016952
• Beilstein号: 263823
• 默克索引号: 144391
• PubChem SID: 46509060; 24278036; 24895273; 160964881
• PubChem CID: 5280961
• CHEBI ID: 28088
• CHEMBL: 44
• Chemspider ID: 4444448
• DrugBank ID: DB01645
• KEGG ID: C06563
• 美国药典/FDA物质标识码: DH2M523P0H
• 维基百科标题: Genistein

理论计算性质

JChem

• Acid pKa: 6.54627
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): 3.0396812
• LogD (pH = 7.4): 2.1150076
• Log P: 3.0768723
• 摩尔折射率: 71.6829 cm^3
• 极化性: 27.108362 Å^3
• 极化表面积: 86.99 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.04
• LOG S: -3.34
• 溶解度: 1.23e-01 g/l

分子性质

理化性质

• 溶解度: DMSO; DMSO: soluble; ethanol: soluble; Methanol
• 外观: off-white powder; Powder; Tan to Light Yellow Solid
• 熔点: 297-298°C; 298-300°C (dec.); ca 300°C

安全信息

• 保存条件: 0°C; -20°C; -20°C Freezer
• 保存注意事项: IRRITANT
• RTECS编号: NR2392000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22
• TSCA收录: false; 是
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 个人保护装置: Eyeshields, Faceshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C; 2-8°C

药理学性质

• 作用靶点: EGFR EGFR
• 相关基因信息: human ... AKT1(207), CYP19A1(1588), EGFR(1956), ESR1(2099), ESR2(2100)mouse ... Esr1(13982), Hexa(15211)rat ... Adora1(29290), Adora2a(25369), Ar(24208)
• 生物活性机理: Against protein tyrosine kinases including those activated by epidermal growth factor (EGRF) and platelet derived growth factor (PDGF) receptors; Antioxidant; Protein kinase inhibitor

产品相关信息

• 纯度: ~98% (HPLC); ≥97% (HPLC); ≥98% (HPLC); 97%; 98.5
• 级别: analytical standard
• 成盐信息: Free Base
• 生物来源: 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
• 有效期: (limited shelf life, expiry date on the label)
• 应用领域: 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

详细说明

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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