(8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-8-[(1R)-1-hydroxyethyl]-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

• ChemBase编号: 165428
• 分子式: C27H31NO10
• 平均质量: 529.53574
• 单一同位素质量: 529.1947962
• SMILES: c1cc(c2c(c1)C(=O)c1c(C2=O)c(c2c(c1O)C[C@@](C[C@@H]2O[C@H]1C[C@H]([C@@H]([C@@H](O1)C)O)N)(O)[C@H](O)C)O)OC
• Canonical SMILES: COc1cccc2c1C(=O)c1c(C2=O)c(O)c2c(c1O)[C@@H](O[C@H]1C[C@@H](N)[C@@H]([C@@H](O1)C)O)C[C@](C2)(O)[C@H](O)C
• InChI: InChI=1S/C27H31NO10/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33/h4-6,10-11,14,16-17,22,29-30,32,34-35H,7-9,28H2,1-3H3/t10-,11+,14-,16-,17-,22+,27-/m0/s1
• InChIKey: HJEZFVLKJYFNQW-OXCIRTNUSA-N

名称和登记号

名称

• IUPAC标准名: (8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-8-[(1R)-1-hydroxyethyl]-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
• IUPAC传统名: dihydrodaunomycin
• 别名: (8S,10S)-10-[(3-Amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-[1-hydroxyethyl]-1-methoxy-5,12-naphthacenedione; 13-Dihydrodaunorubicin; Duborimycin; Leukaemomycin D; Daunorubicinol (Mixture of Diastereomers)

登记号

• PubChem SID: 162259561
• PubChem CID: 71315194

理论计算性质

• Acid pKa: 9.736299
• 质子受体: 11
• 质子供体: 6
• LogD (pH = 5.5): -1.0412652
• LogD (pH = 7.4): -0.02799974
• Log P: 1.2748721
• 摩尔折射率: 133.8167 cm^3
• 极化性: 52.490555 Å^3
• 极化表面积: 189.0 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: Chloroform; Dichloromethane; DMSO; Methanol
• 外观: Red Solid
• 熔点: 179-181°C

安全信息

• 保存条件: -20°C Freezer

详细说明

Toronto Research Chemicals - D194510

A metabolite of Daunorubicin. Used as an antineoplastic. Complexes with DNA. Inhibits DNA and RNA synthesis.

参考文献

• Mizuno, N.S., et al.: Cancer Res., 35, 1542 (1975)
• Munger, C., et al.: Cancer Res., 48, 2404 (1975)
• Kobayashi, Y., et al.: J. Biol. Chem., 275, 17639 ( 2000), Burke, B., et al.: Cardiovasc. Toxicol., 2, 41 (1975)