(4S,7R,8S,9S,13Z)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione

• ChemBase编号: 168109
• 分子式: C27H41NO5S
• 平均质量: 491.68314
• 单一同位素质量: 491.27054442
• SMILES: C\1=C(\CCC[C@@H]([C@@H]([C@H](C(=O)C([C@H](CC(=O)OC(C1)/C(=C/c1csc(n1)C)/C)O)(C)C)C)O)C)/C
• Canonical SMILES: O=C1OC(C/C=C(/C)\CCC[C@@H]([C@@H]([C@H](C(=O)C([C@H](C1)O)(C)C)C)O)C)/C(=C/c1csc(n1)C)/C
• InChI: InChI=1S/C27H41NO5S/c1-16-9-8-10-17(2)25(31)19(4)26(32)27(6,7)23(29)14-24(30)33-22(12-11-16)18(3)13-21-15-34-20(5)28-21/h11,13,15,17,19,22-23,25,29,31H,8-10,12,14H2,1-7H3/b16-11-,18-13+/t17-,19+,22?,23-,25-/m0/s1
• InChIKey: XOZIUKBZLSUILX-AEEURSPKSA-N

名称和登记号

名称

• IUPAC标准名: (4S,7R,8S,9S,13Z)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione
• IUPAC传统名: (4S,7R,8S,9S,13Z)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione
• 别名: (4S,7R,8S,9S,13Z,16S)-4,8-Dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]oxacyclohexadec-13-ene-2,6-dione; (-)-Desoxyepothilone B; (-)-Epothilone D; 12,13-Deoxyepothilone B; 12,13-Desoxyepothilone B; Desoxyepothilone B; Epo D; Epothilone D; KOS 862; NSC 703147; Epothilone D (synthetic)

登记号

• CAS号: 189453-10-9
• PubChem SID: 162262241
• PubChem CID: 6440032

理论计算性质

• Acid pKa: 14.086924
• 质子受体: 5
• 质子供体: 2
• LogD (pH = 5.5): 5.0955997
• LogD (pH = 7.4): 5.0963
• Log P: 5.096309
• 摩尔折射率: 136.0431 cm^3
• 极化性: 53.16778 Å^3
• 极化表面积: 96.72 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: Chloroform; DMSO; Ether; Ethyl Acetate; Methanol
• 外观: White Solid
• 熔点: 63-66°C

安全信息

• 保存条件: -20°C Freezer

详细说明

Toronto Research Chemicals - E589000

Epothilones are polyketide natural products that inhibit cancer cells by a mechanism similar to paclitaxel, and also are effective against paclitaxel-resistant tumours. Epothilone D is in phase I clinical testing of in patients with advanced solid tumou

参考文献

• Bollag, D.M., et al.: Cancer. Res., 55, 2325 (1995)
• Hardt, I.H., et al.: J. Nat. Prod., 64, 847 (1995)
• Gerth, K., et al.: J. Antibiot., 55, 41, 45 (2002)