N-[(10S)-3,4,14-trimethoxy-13-oxo-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tricyclo[9.5.0.02,7]hexadeca-1(16),2(7),3,5,11,14-hexaen-10-yl]acetamide

• ChemBase编号: 164946
• 分子式: C27H33NO11
• 平均质量: 547.55102
• 单一同位素质量: 547.20536088
• SMILES: c12c([C@H](CCc3c1c(c(c(c3)O[C@H]1[C@@H]([C@@H]([C@@H]([C@H](O1)CO)O)O)O)OC)OC)NC(=O)C)cc(=O)c(cc2)OC
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2cc3CC[C@@H](c4c(c3c(c2OC)OC)ccc(c(=O)c4)OC)NC(=O)C)[C@@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C27H33NO11/c1-12(30)28-16-7-5-13-9-19(38-27-24(34)23(33)22(32)20(11-29)39-27)25(36-3)26(37-4)21(13)14-6-8-18(35-2)17(31)10-15(14)16/h6,8-10,16,20,22-24,27,29,32-34H,5,7,11H2,1-4H3,(H,28,30)/t16-,20+,22+,23-,24+,27+/m0/s1
• InChIKey: UXAFRQPVHYZDED-ZZEDUEFDSA-N

名称和登记号

名称

• IUPAC标准名: N-[(10S)-3,4,14-trimethoxy-13-oxo-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tricyclo[9.5.0.0^2,^7]hexadeca-1(16),2(7),3,5,11,14-hexaen-10-yl]acetamide
• IUPAC传统名: N-[(10S)-3,4,14-trimethoxy-13-oxo-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tricyclo[9.5.0.0^2,^7]hexadeca-1(16),2(7),3,5,11,14-hexaen-10-yl]acetamide
• 别名: (S)-N-[3-(β-D-Glucopyranosyloxy)-5,6,7,9-tetrahydro-1,2,10-trimethoxy-9-oxobenzo[a]heptalen-7-yl]acetamide; N-[(7S)-3-(β-D-Glucopyranosyloxy)-5,6,7,9-tetrahydro-1,2,10-trimethoxy-9-oxobenzo[a]heptalen-7-yl]acetamide; 3-Demethylcolchicine Glucoside; Colchicoside

登记号

• CAS号: 477-29-2
• PubChem SID: 162259080
• PubChem CID: 92763

理论计算性质

• Acid pKa: 12.199023
• 质子受体: 11
• 质子供体: 5
• LogD (pH = 5.5): -0.9519749
• LogD (pH = 7.4): -0.9519805
• Log P: -0.95197356
• 摩尔折射率: 139.0377 cm^3
• 极化性: 53.51496 Å^3
• 极化表面积: 173.24 Å^2
• 可自由旋转的化学键: 7
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: DMSO; Methanol
• 外观: Pale Yellow Solid
• 熔点: 194-197°C

安全信息

• 保存条件: Refrigerator

详细说明

Toronto Research Chemicals - C640050

A significantly toxic Colchicine analog with no anti-inflammatory properties.

参考文献

• Chaudhuri, P., et al.: J. Nat. Prod., 56, 1174 (1993)
• Gomez, D., et al.: J. Chem. Ecol., 29, 1117 (1993)
• Poutaraud, A., et al.: Environ. Exper. Botany, 54, 101 (1993)