(2R,3R,4R,5S,6S)-6-{[(5E)-2,2-dimethyl-7-[methyl(naphthalen-1-ylmethyl)amino]hept-5-en-3-yn-1-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase编号: 171345
• 分子式: C27H33NO7
• 平均质量: 483.55342
• 单一同位素质量: 483.2257024
• SMILES: c12c(cccc1CN(C/C=C/C#CC(CO[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)C(=O)O)(C)C)C)cccc2
• Canonical SMILES: CN(Cc1cccc2c1cccc2)C/C=C/C#CC(CO[C@H]1O[C@H](C(=O)O)[C@@H]([C@H]([C@H]1O)O)O)(C)C
• InChI: InChI=1S/C27H33NO7/c1-27(2,17-34-26-23(31)21(29)22(30)24(35-26)25(32)33)14-7-4-8-15-28(3)16-19-12-9-11-18-10-5-6-13-20(18)19/h4-6,8-13,21-24,26,29-31H,15-17H2,1-3H3,(H,32,33)/b8-4+/t21-,22-,23+,24-,26+/m1/s1
• InChIKey: XWKOYVRIRYSRSH-DSRSGAICSA-N

名称和登记号

名称

• IUPAC标准名: (2R,3R,4R,5S,6S)-6-{[(5E)-2,2-dimethyl-7-[methyl(naphthalen-1-ylmethyl)amino]hept-5-en-3-yn-1-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC传统名: (2R,3R,4R,5S,6S)-6-{[(5E)-2,2-dimethyl-7-[methyl(naphthalen-1-ylmethyl)amino]hept-5-en-3-yn-1-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• 别名: (E)-2,2-Dimethyl-7-[methyl(1-naphthalenylmethyl)amino]-5-hepten-3-ynyl β-D-Glucopyranosiduronic Acid; Hydroxy Terbinafine β-D-Glucuronide

登记号

• CAS号: 99473-12-8
• PubChem SID: 164227255
• PubChem CID: 71749360

理论计算性质

• Acid pKa: 3.1297202
• 质子受体: 8
• 质子供体: 4
• LogD (pH = 5.5): 0.063984066
• LogD (pH = 7.4): 0.05529527
• Log P: 0.06474626
• 摩尔折射率: 132.1306 cm^3
• 极化性: 52.348145 Å^3
• 极化表面积: 119.69 Å^2
• 可自由旋转的化学键: 10
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Methanol
• 外观: Yellow Solid
• 熔点: 105-107°C

详细说明

Toronto Research Chemicals - H956175

A metabolite of Terbinafine, an orally active, antimycotic allylamine related to naftifine. A specfic inhibitor of squalene epoxidase, a key enzyme in fungal ergosterol biosynthesis.

参考文献

• Gazinger, U., et al.: Proc. 13th Int. Congr. Chemother., 6, 116/52 (1983)
• Shadomy, S., et al.: Sabouraudia, 23, 125 (1983)
• Evans, E.G.V., et al.: Brit. Med. J., 318, 1031 (1999)