(1S,4S,5R,8S,9R,12R)-11-hydroxy-1,5,9-trimethyl-14,15,16-trioxa-11-azatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one

• ChemBase编号: 170137
• 分子式: C15H23NO5
• 平均质量: 297.34682
• 单一同位素质量: 297.15762284
• SMILES: [C@@H]1([C@H]2C34[C@@H](CC1)[C@H](C(=O)N([C@@H]3O[C@@](CC2)(C)OO4)O)C)C
• Canonical SMILES: O=C1N(O)[C@@H]2O[C@]3(C)CC[C@@H]4C2([C@H]([C@H]1C)CC[C@H]4C)OO3
• InChI: InChI=1S/C15H23NO5/c1-8-4-5-11-9(2)12(17)16(18)13-15(11)10(8)6-7-14(3,19-13)20-21-15/h8-11,13,18H,4-7H2,1-3H3/t8-,9-,10+,11+,13-,14+,15?/m1/s1
• InChIKey: CIMKGYLLDNUUNG-XRNKLDBLSA-N

名称和登记号

名称

• IUPAC标准名: (1S,4S,5R,8S,9R,12R)-11-hydroxy-1,5,9-trimethyl-14,15,16-trioxa-11-azatetracyclo[10.3.1.0^4,^1^3.0^8,^1^3]hexadecan-10-one
• IUPAC传统名: (1S,4S,5R,8S,9R,12R)-11-hydroxy-1,5,9-trimethyl-14,15,16-trioxa-11-azatetracyclo[10.3.1.0^4,^1^3.0^8,^1^3]hexadecan-10-one
• 别名: (3R,5aS,6R,8aS,9R,12R,12aR)-11-Hydroxydecahydro-3,6,9-trimethyl-3,12-epoxy-1,2-dioxepino[4,3-i]isoquinolin-10(3H)-one; N-Hydroxy-11-azaartemisinin

登记号

• CAS号: 1086409-82-6
• PubChem SID: 164226047
• PubChem CID: 71748824

理论计算性质

• Acid pKa: 7.3893065
• 质子受体: 5
• 质子供体: 1
• LogD (pH = 5.5): 2.3761714
• LogD (pH = 7.4): 2.0771732
• Log P: 2.3817158
• 摩尔折射率: 72.3961 cm^3
• 极化性: 29.449991 Å^3
• 极化表面积: 68.23 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: Chloroform; Methanol
• 外观: White Solid
• 熔点: 187-190°C

安全信息

• 保存条件: Amber Vial, -20°C Freezer, Under Inert Atmosphere

详细说明

Toronto Research Chemicals - H804500

A derivative of 11-Azaartemisinin which showed a high order of activity against multidrug-resistant malaria by oral route.

参考文献

• Meshnick, S.R., et al.: Microbiol. Rev., 60, 301 (1996)
• O’Neill, P.M., et al.: J. Med. Chem., 45, 1052 (1996)
• Rottmann, M., et al.: J. Med. Chem., 51, 1035 (1996)