(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1,9-dihydroxy-15-{[(2R,3S)-2-hydroxy-3-[(2E)-2-methylbut-2-enamido]-3-phenylpropanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl benzoate

• ChemBase编号: 163979
• 分子式: C45H53NO14
• 平均质量: 831.90062
• 单一同位素质量: 831.34660538
• SMILES: C12=C([C@H](C[C@](C1(C)C)([C@H]([C@H]1[C@](C(=O)[C@@H]2OC(=O)C)([C@H](C[C@@H]2[C@]1(CO2)OC(=O)C)O)C)OC(=O)c1ccccc1)O)OC(=O)[C@@H]([C@H](c1ccccc1)NC(=O)/C(=C/C)/C)O)C
• Canonical SMILES: C/C=C(/C(=O)N[C@H]([C@H](C(=O)O[C@H]1C[C@@]2(O)[C@@H](OC(=O)c3ccccc3)[C@@H]3[C@@]4(CO[C@@H]4C[C@@H]([C@]3(C(=O)[C@@H](C(=C1C)C2(C)C)OC(=O)C)C)O)OC(=O)C)O)c1ccccc1)\C
• InChI: InChI=1S/C45H53NO14/c1-9-23(2)39(52)46-33(27-16-12-10-13-17-27)34(50)41(54)58-29-21-45(55)38(59-40(53)28-18-14-11-15-19-28)36-43(8,30(49)20-31-44(36,22-56-31)60-26(5)48)37(51)35(57-25(4)47)32(24(29)3)42(45,6)7/h9-19,29-31,33-36,38,49-50,55H,20-22H2,1-8H3,(H,46,52)/b23-9+/t29-,30-,31+,33-,34+,35+,36-,38-,43+,44-,45+/m0/s1
• InChIKey: DBXFAPJCZABTDR-WBYYIXQISA-N

名称和登记号

名称

• IUPAC标准名: (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1,9-dihydroxy-15-{[(2R,3S)-2-hydroxy-3-[(2E)-2-methylbut-2-enamido]-3-phenylpropanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^3,^1^0.0^4,^7]heptadec-13-en-2-yl benzoate
• IUPAC传统名: (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1,9-dihydroxy-15-{[(2R,3S)-2-hydroxy-3-[(2E)-2-methylbut-2-enamido]-3-phenylpropanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^3,^1^0.0^4,^7]heptadec-13-en-2-yl benzoate
• 别名: (αR,βS)-α-Hydroxy-β-[[(2E)-2-methyl-1-oxo-2-buten-1-yl]amino]benzenepropanoic Acid (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl Ester; NSC 318735; Taxol B; Cephalomannine

登记号

• CAS号: 71610-00-9
• PubChem SID: 162258114
• PubChem CID: 6436208

理论计算性质

• Acid pKa: 10.363954
• 质子受体: 10
• 质子供体: 4
• LogD (pH = 5.5): 3.2230601
• LogD (pH = 7.4): 3.2226717
• Log P: 3.223144
• 摩尔折射率: 212.3023 cm^3
• 极化性: 84.30143 Å^3
• 极化表面积: 221.29 Å^2
• 可自由旋转的化学键: 14
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: Chlorform; DMSO; Methanol
• 外观: Off-White Solid
• 熔点: 139-141°C

安全信息

• 保存条件: -20°C Freezer

详细说明

Toronto Research Chemicals - C258500

Antitumor, antiproliferative.

参考文献

• Stenken, J., et al.: J. Pharm. Sci., 86, 958 (1997)
• Kobayashi, J., et al.: Bioorg. Med. Chem. Lett., 8, 1555 (1997)
• Andreu, J., et al.: Biochemistry, 40, 11975 (1997)
• Markman, M., et al.: J. Clin. Oncol., 24, 988 (1997)