3-hydroxy-2-[(6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-5-pentylcyclohexa-2,5-diene-1,4-dione

• ChemBase编号: 163586
• 分子式: C21H28O3
• 平均质量: 328.44522
• 单一同位素质量: 328.20384476
• SMILES: C1=C(C(=O)C(=C(C1=O)C1[C@@H](CCC(=C1)C)C(=C)C)O)CCCCC
• Canonical SMILES: CCCCCC1=CC(=O)C(=C(C1=O)O)C1C=C(C)CC[C@H]1C(=C)C
• InChI: InChI=1S/C21H28O3/c1-5-6-7-8-15-12-18(22)19(21(24)20(15)23)17-11-14(4)9-10-16(17)13(2)3/h11-12,16-17,24H,2,5-10H2,1,3-4H3/t16-,17?/m0/s1
• InChIKey: WDXXEUARVHTWQF-BHWOMJMDSA-N

名称和登记号

名称

• IUPAC标准名: 3-hydroxy-2-[(6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-5-pentylcyclohexa-2,5-diene-1,4-dione
• IUPAC传统名: 3-hydroxy-2-[(6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-5-pentylcyclohexa-2,5-diene-1,4-dione
• 别名: 3-Hydroxy-2-[(1R,6R)-3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-2,5-Cyclohexadiene-1,4-dione; (1R-trans)-3-Hydroxy-2-[3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-2,5-cyclohexadiene-1,4-dione; HU 331; Cannabidiol Hydroxyquinone

登记号

• CAS号: 137252-25-6
• PubChem SID: 162257721
• PubChem CID: 126249

理论计算性质

• Acid pKa: 8.866102
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 5.2286134
• LogD (pH = 7.4): 5.2142043
• Log P: 5.2288003
• 摩尔折射率: 100.1391 cm^3
• 极化性: 37.75317 Å^3
• 极化表面积: 54.37 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: DMSO; Methanol
• 外观: Orange Solid
• 熔点: 48-50°C

安全信息

• 保存条件: Controlled Substance, Amber Vial, -20°C Freezer, Under Inert Atmosphere

详细说明

Toronto Research Chemicals - C175315

A cannabinoid anticancer quinone, HU-331, is more potent and less cardiotoxic than Doxorubicin and thus it has a high potential for development as a new anticancer drug.

参考文献

• Dana, B., et al.: J. Clin. Oncol., 11, 644 (1993)
• Feleszko, W., et al.: Clin. Cancer Res., 6, 2044 (1993)
• Kogan, N., et al.: J. Med. Chem., 47, 3800 (1993)