4-[(1S,2R,5S,7S,10R,11S,14R,15R)-5,7,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]-2,5-dihydrofuran-2-one

• ChemBase编号: 179727
• 分子式: C23H34O5
• 平均质量: 390.51306
• 单一同位素质量: 390.24062419
• SMILES: [C@@]12([C@@]([C@@H](C3=CC(=O)OC3)CC2)(CC[C@@H]2[C@@]3([C@@](C[C@H](CC3)O)(CC[C@@H]12)O)C)C)O
• Canonical SMILES: O[C@H]1CC[C@]2([C@](C1)(O)CC[C@@H]1[C@@H]2CC[C@]2([C@]1(O)CC[C@@H]2C1=CC(=O)OC1)C)C
• InChI: InChI=1S/C23H34O5/c1-20-7-3-15(24)12-22(20,26)9-5-18-17(20)4-8-21(2)16(6-10-23(18,21)27)14-11-19(25)28-13-14/h11,15-18,24,26-27H,3-10,12-13H2,1-2H3/t15-,16+,17-,18+,20+,21+,22-,23-/m0/s1
• InChIKey: QJPCKAJTLHDNCS-FBAXFMHRSA-N

名称和登记号

名称

• IUPAC标准名: 4-[(1S,2R,5S,7S,10R,11S,14R,15R)-5,7,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]-2,5-dihydrofuran-2-one
• IUPAC传统名: 4-[(1S,2R,5S,7S,10R,11S,14R,15R)-5,7,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]-2,5-dihydrofuran-2-one
• 别名: Periplogenin

登记号

• CAS号: 514-39-6
• PubChem SID: 164235637
• PubChem CID: 10574

理论计算性质

• Acid pKa: 7.1826363
• 质子受体: 4
• 质子供体: 3
• LogD (pH = 5.5): 1.826343
• LogD (pH = 7.4): 1.4129112
• Log P: 1.8352609
• 摩尔折射率: 105.1251 cm^3
• 极化性: 41.84968 Å^3
• 极化表面积: 86.99 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

药理学性质

• 生物活性机理: Apoptosis inductor

产品相关信息

• 生物来源: Aglycone from Alloemicymarin, also in seeds of Speirantha preussii
• 应用领域: Antiproliferative activity toward three human-derived (HT-1080 fibrosarcoma, lung A549 adenocarcinoma, cervix HeLa adenocarcinoma)

参考文献

• Speiser, P. et al., Experientia, 1947, 3, 323, (isol)
• Speiser, P. et al., Helv. Chim. Acta, 1948, 31, 622, (struct)
• Lichti, H. et al., Helv. Chim. Acta, 1956, 39, 1914, (Ledienoside, Periplogenin digitoxoside)
• Zelnik, R. et al., Helv. Chim. Acta, 1957, 40, 2110
• Deghenghi, R. et al., Tet. Lett., 1963, 2045, (synth)
• Shoji, J. et al., Chem. Pharm. Bull., 1967, 15, 720, (isol)
• Sauer, H.H. et al., Phytochemistry, 1968, 7, 1543, (biosynth)
• Kamano, Y. et al., J.C.S. Perkin 1, 1975, 1976, (synth)
• Pauli, G.F., Planta Med., 1995, 61, 162, (Periplorhamnoside, Periplogenin glucoside, pmr)