(1S,2R,8S)-14-oxa-7-azatetracyclo[6.6.1.01,11.02,7]pentadeca-9,11-dien-13-one

• ChemBase编号: 155034
• 分子式: C13H15NO2
• 平均质量: 217.2637
• 单一同位素质量: 217.11027873
• SMILES: C1CCN2[C@H](C1)[C@]13C[C@@H]2C=CC1=CC(=O)O3
• Canonical SMILES: O=C1C=C2[C@@]3(O1)C[C@H](C=C2)N1[C@@H]3CCCC1
• InChI: InChI=1S/C13H15NO2/c15-12-7-9-4-5-10-8-13(9,16-12)11-3-1-2-6-14(10)11/h4-5,7,10-11H,1-3,6,8H2/t10-,11-,13+/m1/s1
• InChIKey: SWZMSZQQJRKFBP-WZRBSPASSA-N

名称和登记号

名称

• IUPAC标准名: (1S,2R,8S)-14-oxa-7-azatetracyclo[6.6.1.0^1,^1^1.0^2,^7]pentadeca-9,11-dien-13-one
• IUPAC传统名: (-)-securinine
• 别名: Securinine

登记号

• CAS号: 5610-40-2
• MDL号: MFCD00078775
• PubChem SID: 162249172
• PubChem CID: 442872

理论计算性质

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): -1.9773666
• LogD (pH = 7.4): -0.68543625
• Log P: 1.4055138
• 摩尔折射率: 61.3191 cm^3
• 极化性: 23.567463 Å^3
• 极化表面积: 29.54 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO: ≥25 mg/mL
• 外观: yellow powder
• 比旋光度: [α]/D -980 to -1015 ( C=1, MeOH)

安全信息

• RTECS编号: VS4115000
• 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
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C13H15NO2
• 分类: Genuine Natural Compounds

详细说明

Sigma Aldrich - SML0055

Biochem/physiol Actions
Securinine is an alkaloid widely in traditional folk medicine. Long known as a GABAA antagonist, securinine was recently found to up-regulate p53 protein and to modulate the related family member p73 protein in a p53-dependent fashion, inducing p73 in the HCT116 p53(-) cells and down-regulating it in the p53(+) cells. Induction of proapoptotic protein p73 only in p53 cells could be used to target cancer cells preferentially. Securinine has been found to induce p53-independent, p73-dependent apoptosis in RKO colon cancer cells.