(1S,2S,3R,4S,7R,9S,11R,13S,16S)-4,13-bis(acetyloxy)-16-{[(2R,3S)-3-{[(tert-butoxy)carbonyl]amino}-2-hydroxy-3-phenylpropanoyl]oxy}-1-hydroxy-15,18,18-trimethyl-12-oxo-6-oxapentacyclo[12.3.1.03,11.04,7.09,11]octadec-14-en-2-yl benzoate

• ChemBase编号: 172226
• 分子式: C45H53NO14
• 平均质量: 831.90062
• 单一同位素质量: 831.34660538
• SMILES: C1(=C2C([C@@](C[C@@H]1OC(=O)[C@@H]([C@@H](NC(=O)OC(C)(C)C)c1ccccc1)O)([C@H]([C@H]1[C@]3(C(=O)[C@H]2OC(=O)C)[C@H](C[C@@H]2[C@]1(CO2)OC(=O)C)C3)OC(=O)c1ccccc1)O)(C)C)C
• Canonical SMILES: CC(=O)O[C@@H]1C(=O)[C@]23C[C@H]2C[C@@H]2[C@]([C@H]3[C@@H]([C@]3(C(C1=C(C)[C@@H](OC(=O)[C@@H]([C@H](c1ccccc1)NC(=O)OC(C)(C)C)O)C3)(C)C)O)OC(=O)c1ccccc1)(CO2)OC(=O)C
• InChI: InChI=1S/C45H53NO14/c1-23-29(57-39(52)33(49)32(26-15-11-9-12-16-26)46-40(53)60-41(4,5)6)21-45(54)37(58-38(51)27-17-13-10-14-18-27)35-43(36(50)34(56-24(2)47)31(23)42(45,7)8)20-28(43)19-30-44(35,22-55-30)59-25(3)48/h9-18,28-30,32-35,37,49,54H,19-22H2,1-8H3,(H,46,53)/t28-,29+,30-,32+,33-,34+,35+,37+,43-,44+,45-/m1/s1
• InChIKey: DXOJIXGRFSHVKA-ZPXGHFPSSA-N

名称和登记号

名称

• IUPAC标准名: (1S,2S,3R,4S,7R,9S,11R,13S,16S)-4,13-bis(acetyloxy)-16-{[(2R,3S)-3-{[(tert-butoxy)carbonyl]amino}-2-hydroxy-3-phenylpropanoyl]oxy}-1-hydroxy-15,18,18-trimethyl-12-oxo-6-oxapentacyclo[12.3.1.0^3,^1^1.0^4,^7.0^9,^1^1]octadec-14-en-2-yl benzoate
• IUPAC传统名: (1S,2S,3R,4S,7R,9S,11R,13S,16S)-4,13-bis(acetyloxy)-16-{[(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoyl]oxy}-1-hydroxy-15,18,18-trimethyl-12-oxo-6-oxapentacyclo[12.3.1.0^3,^1^1.0^4,^7.0^9,^1^1]octadec-14-en-2-yl benzoate
• 别名: (αR,βS)-β-[[(1,1-Dimethylethoxy)carbonyl]amino]-α-hydroxybenzenepropanoic Acid (1S,2S,4S,7R,8aR,9aS,10aR,12aS,12bR)-7,12a-Bis(acetyloxy)-1-(benzoyloxy)-1,3,4,7,8,9,9a,10,10a,12,12a,12b-dodecahydro-2-hydroxy-5,13,13-trimethyl-8-oxo-2,6-methano-2H-cyclodeca[3,4]cyclopropa[4,5]benz[1,2-b]oxet-4-yl Ester; PNU 100940; Larotaxel

登记号

• CAS号: 156294-36-9
• PubChem SID: 164228136
• PubChem CID: 71749750

理论计算性质

• Acid pKa: 11.262049
• 质子受体: 9
• 质子供体: 3
• LogD (pH = 5.5): 4.040245
• LogD (pH = 7.4): 4.0401864
• Log P: 4.040246
• 摩尔折射率: 209.7267 cm^3
• 极化性: 83.903595 Å^3
• 极化表面积: 210.29 Å^2
• 可自由旋转的化学键: 15
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: Chloroform; Methanol
• 外观: White Solid
• 熔点: 180-182°C

安全信息

• 保存条件: -20°C Freezer

详细说明

Toronto Research Chemicals - L176000

Larotaxel (RPR 109881A) is a taxane analog with a broad spectrum of activity and different toxicity profile and with the possible advantages of surpassing some mechanisms of resistance and penetrating into the CNS.

参考文献

• Kurata, T., et al.: J. Clin. Oncol., 18, 3164 (2000)
• Kemper, E., et al.: Eur. J. Cancer, 40, 1269 (2000)
• Nyman, D., et al.: J. Clin. Oncol., 23, 7785 (2000)