(1S,3R,6S,8R,11S,12S,14R,15S,16R)-7,7,12,16-tetramethyl-6-(methylamino)-15-[(1S)-1-(methylamino)ethyl]pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-14-ol

• ChemBase编号: 73022
• 分子式: C26H46N2O
• 平均质量: 402.65624
• 单一同位素质量: 402.3610141
• SMILES: C1[C@@H](C([C@H]2[C@]3(C1)[C@]1([C@@H](CC2)[C@]2([C@](CC1)([C@H]([C@@H](C2)O)[C@H](C)NC)C)C)C3)(C)C)NC
• Canonical SMILES: CN[C@H]([C@H]1[C@H](O)C[C@@]2([C@]1(C)CC[C@@]13[C@H]2CC[C@@H]2[C@]3(C1)CC[C@@H](C2(C)C)NC)C)C
• InChI: InChI=1S/C26H46N2O/c1-16(27-6)21-17(29)14-24(5)19-9-8-18-22(2,3)20(28-7)10-11-25(18)15-26(19,25)13-12-23(21,24)4/h16-21,27-29H,8-15H2,1-7H3/t16-,17+,18-,19-,20-,21-,23+,24-,25+,26-/m0/s1
• InChIKey: GMNAPBAUIVITMI-ABNIRSKTSA-N

名称和登记号

名称

• IUPAC标准名: (1S,3R,6S,8R,11S,12S,14R,15S,16R)-7,7,12,16-tetramethyl-6-(methylamino)-15-[(1S)-1-(methylamino)ethyl]pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-14-ol
• IUPAC传统名: (1S,3R,6S,8R,11S,12S,14R,15S,16R)-7,7,12,16-tetramethyl-6-(methylamino)-15-[(1S)-1-(methylamino)ethyl]pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-14-ol
• 别名: Bebuxine; Cyclovirobuxine; Cyclovirobuxine D; NSC 91722; Cyclovirobuxin D(Bebuxine)

登记号

• CAS号: 860-79-7
• PubChem SID: 162037942
• PubChem CID: 260439

理论计算性质

• Acid pKa: 14.865901
• 质子受体: 3
• 质子供体: 3
• LogD (pH = 5.5): -2.9480493
• LogD (pH = 7.4): -2.2235258
• Log P: 3.5204458
• 摩尔折射率: 119.7864 cm^3
• 极化性: 48.67277 Å^3
• 极化表面积: 44.29 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

安全信息

• 保存条件: -20°C

产品相关信息

• 成盐信息: Free Base

详细说明

Selleck Chemicals - S2402

Research Area: Cardiovascular Disease
Biological Activity:
Cyclovirobuxine D (bebuxine; Cyclovirobuxine) is an active compound extracted from Buxus microphylla, which has been used for treating acute myocardial ischemia. Cyclovirobuxine D (bebuxine; Cyclovirobuxine) significantly increased cardiomyocytes viability injured by oxidation or hypoxia. It significantly reduced the infarct size induced by ligating the coronary artery in rats, and the effect was almost abolished by glibenclamide, a blocker of ATP sensitive potassium channel, but it was not influenced by cyclooxygenase-2 inhibitor celecoxib or estrogen receptor antagonist tamoxifen. In addition, cyclovirobuxine D (bebuxine; Cyclovirobuxine) significantly protected rat aorta endothelial cells against hypoxia and enhanced nitric oxide (NO) release from endothelial cells, which was inhibited by nitric oxide synthase (NOS) inhibitor N-nitro-l-arginine methyl ester (L-NAME). Furthermore, cyclovirobuxine D (bebuxine; Cyclovirobuxine) significantly decreased the weight of venous thrombus in rats. [1][2]

参考文献

• Grossini E et al. Life Sci. 1999;65(5):PL59-65.