5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

• ChemBase编号: 5003
• 分子式: C15H10O5
• 平均质量: 270.2369
• 单一同位素质量: 270.05282342
• SMILES: c1cc(O)ccc1c1oc2c(c(=O)c1)c(cc(c2)O)O
• Canonical SMILES: Oc1ccc(cc1)c1cc(=O)c2c(o1)cc(cc2O)O
• InChI: InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-7,16-18H
• InChIKey: KZNIFHPLKGYRTM-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
• IUPAC传统名: chamomile; 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
• 别名: 4',5,7-三羟基黄酮; 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one; 4',5,7-Trihydroxyflavone; N-[4-(1-Cyanocyclopentyl)phenyl]-2-[[(1-oxido-4-pyridinyl)methyl]amino]-3-pyridinecarboxamide; Apatinib 25-N-Oxide Hydrochloride; Apigenine; Chamomile; Apigenol; Spigenin; Versulin; C.I. Natural Yellow 1; 4′,5,7-Trihydroxyflavone; Apigenin; Apigenin; Apigenin; 4',5,7-Trihydroxyflavone; Pelargidenone

登记号

• CAS号: 520-36-5; 520-36-5
• EC号: 208-292-3
• MDL号: MFCD00006831
• Beilstein号: 262620
• 默克索引号: 14730
• PubChem SID: 24846790; 24278212; 99443823; 160968435
• PubChem CID: 5280443
• CHEBI ID: 18388
• CHEMBL: 28
• Chemspider ID: 4444100
• DrugBank ID: DB07352
• KEGG ID: C01477
• 维基百科标题: Apigenin

理论计算性质

JChem

• Acid pKa: 6.574692
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): 2.671756
• LogD (pH = 7.4): 1.7656507
• Log P: 2.7066891
• 摩尔折射率: 72.9139 cm^3
• 极化性: 27.10717 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: 3.07
• LOG S: -3.36
• 溶解度: 1.18e-01 g/l

分子性质

理化性质

• 溶解度: 1 M KOH: soluble50 mg/mL; DMSO: soluble27 mg/mL; H2O: insoluble
• 外观: Yellow crystalline solid; yellow powder; Yellow powder; yellow to green
• 熔点: >300 °C(lit.); 300°C; 345–350 °C; ca 315°C dec.
• 密度: 0.905 g/ml

安全信息

• 保存条件: -20°C
• 保存注意事项: Irritant
• RTECS编号: LK9276000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26-36; 26-37
• TSCA收录: 否
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: -20°C; 2-8°C

药理学性质

• 相关基因信息: human ... ADORA3(140), CDC2(983), CDK5(1020), CDK6(1021), CYP1A2(1544), ESR1(2099), ESR2(2100), GSK3A(2931)mouse ... Hexa(15211)rat ... Adora1(29290), Adora2a(25369), Il4(287287), Tnf(24835)
• 生物活性机理: Tyrosine kinase inhibitor

产品相关信息

• 纯度: ≥75% (HPLC); ≥95.0% (HPLC); ≥97% (TLC); ≥99% (HPLC); 95%; 97%; 99.0
• 级别: analytical standard
• 成盐信息: Free Base
• 杂质: ~2% water; <5% acetic acid; ≤2% water
• 生物来源: Found free or as glycosides in the stems, roots, leaves, seeds or fruit of a very wide range of plant spp. Found also in some fossil leaf tissues; from parsley
• 有效期: (limited shelf life, expiry date on the label)
• 应用领域: Antispasmolytic agent; Shows antineoplastic activity in vitro
• Empirical Formula (Hill Notation): C15H10O5

详细说明

DrugBank - DB07352

Drug information: experimental

Apollo Scientific Ltd - OR7265T

A MAP kinase inhibitor. Also inhibits the proliferation of malignant tumor cells.

Selleck Chemicals - S2262

Research Area: Cancer
Biological Activity:
Apigenin is a potent CYP2C9 inhibitor with an IC50 of 23 pM. CYP2C9 is an enzyme responsible for the metabolism of many pharmaceutical compounds in the body. Apigenin is commonly recognised as to mediate at least part of the chemopreventive action of vegetables and fruits in the cancerous process. Recently it was shown that apigenin induces a process called autophagia (a kind of cellular dormancy) which may well explain it chemopreventive properties but at the same time induces resistance against chemotherapy. Apigenin is a flavone that is the aglycone of several glycosides. [1][2]References on Apigenin[1] http://en.wikipedia.org/wiki/Apigenin, , [2] Drug Metab Dispos., 2009 Mar, 37(3):629-34

Sigma Aldrich - 460745

Biochem/physiol Actions
A plant flavonoid that has been found to inhibit cell proliferation by arresting the cell cycle at the G2/M phase. Inhibition of growth through cell cycle arrest and induction of apoptosis appear to be related to induction of p53.Inhibits PMA-mediated tumor promotion by inhibiting protein kinase C1 and the resulting suppression of oncogene expression. It has also been reported to inhibit topoisomerase I-catalyzed DNA re-ligation and enhance gap junctional intercellular communication.

Sigma Aldrich - A281

Biochem/physiol Actions
A plant flavonoid that has been found to inhibit cell proliferation by arresting the cell cycle at the G2/M phase. Inhibition of growth through cell cycle arrest and induction of apoptosis appear to be related to induction of p53.Inhibits PMA-mediated tumor promotion by inhibiting protein kinase C1 and the resulting suppression of oncogene expression. It has also been reported to inhibit topoisomerase I-catalyzed DNA re-ligation and enhance gap junctional intercellular communication.

Sigma Aldrich - 42251

Biochem/physiol Actions
A plant flavonoid that has been found to inhibit cell proliferation by arresting the cell cycle at the G2/M phase. Inhibition of growth through cell cycle arrest and induction of apoptosis appear to be related to induction of p53.Inhibits PMA-mediated tumor promotion by inhibiting protein kinase C1 and the resulting suppression of oncogene expression. It has also been reported to inhibit topoisomerase I-catalyzed DNA re-ligation and enhance gap junctional intercellular communication.

Sigma Aldrich - 10793

Biochem/physiol Actions
A plant flavonoid that has been found to inhibit cell proliferation by arresting the cell cycle at the G2/M phase. Inhibition of growth through cell cycle arrest and induction of apoptosis appear to be related to induction of p53.Inhibits PMA-mediated tumor promotion by inhibiting protein kinase C1 and the resulting suppression of oncogene expression. It has also been reported to inhibit topoisomerase I-catalyzed DNA re-ligation and enhance gap junctional intercellular communication.

Sigma Aldrich - A3145

Biochem/physiol Actions
A plant flavonoid that has been found to inhibit cell proliferation by arresting the cell cycle at the G2/M phase. Inhibition of growth through cell cycle arrest and induction of apoptosis appear to be related to induction of p53.Inhibits PMA-mediated tumor promotion by inhibiting protein kinase C1 and the resulting suppression of oncogene expression. It has also been reported to inhibit topoisomerase I-catalyzed DNA re-ligation and enhance gap junctional intercellular communication.

Sigma Aldrich - 10798

Other Notes
Inhibitor of human estrogen synthetase2
Biochem/physiol Actions
A plant flavonoid that has been found to inhibit cell proliferation by arresting the cell cycle at the G2/M phase. Inhibition of growth through cell cycle arrest and induction of apoptosis appear to be related to induction of p53.Inhibits PMA-mediated tumor promotion by inhibiting protein kinase C1 and the resulting suppression of oncogene expression. It has also been reported to inhibit topoisomerase I-catalyzed DNA re-ligation and enhance gap junctional intercellular communication.

Toronto Research Chemicals - A726160

Apatinib 25-N-Oxide is a metabolite of the antiangiogenic agent and selective VEGFR2 inhibitor Apatinib (A726150).

参考文献

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