(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[2-methyl-3-(2-methylphenyl)-4-oxo-3,4-dihydroquinazolin-6-yl]oxy}oxane-2-carboxylic acid

• ChemBase编号: 172723
• 分子式: C22H22N2O8
• 平均质量: 442.41868
• 单一同位素质量: 442.13761567
• SMILES: c1c(cc2c(c1)nc(n(c2=O)c1c(cccc1)C)C)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](Oc2ccc3c(c2)c(=O)n(c(n3)C)c2ccccc2C)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C22H22N2O8/c1-10-5-3-4-6-15(10)24-11(2)23-14-8-7-12(9-13(14)20(24)28)31-22-18(27)16(25)17(26)19(32-22)21(29)30/h3-9,16-19,22,25-27H,1-2H3,(H,29,30)/t16-,17-,18+,19-,22+/m0/s1
• InChIKey: WKXWFAVXGQVYFU-KSSXRGRSSA-N

名称和登记号

名称

• IUPAC标准名: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[2-methyl-3-(2-methylphenyl)-4-oxo-3,4-dihydroquinazolin-6-yl]oxy}oxane-2-carboxylic acid
• IUPAC传统名: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[2-methyl-3-(2-methylphenyl)-4-oxoquinazolin-6-yl]oxy}oxane-2-carboxylic acid
• 别名: 3,4-Dihydro-2-methyl-3-(2-methylphenyl)-4-oxo-6-quinazolinyl β-D-Glucopyranosiduronic Acid; Methaqualone 6-O-β-D-Glucuronide

登记号

• CAS号: 67982-37-0
• PubChem SID: 164228633
• PubChem CID: 71749991

理论计算性质

• Acid pKa: 2.762668
• 质子受体: 9
• 质子供体: 4
• LogD (pH = 5.5): -1.7561164
• LogD (pH = 7.4): -2.5797336
• Log P: 0.9171375
• 摩尔折射率: 111.0981 cm^3
• 极化性: 42.5725 Å^3
• 极化表面积: 149.12 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

详细说明

Toronto Research Chemicals - M225985

A glucuronide metabolite Methaqualone (M225900). Controlled substance.

参考文献

• Ericsson, O., et al.: Acta Pharmaceut. Suecica, 15, 81 (1978)
• Wilson, K., et al.: Eur. J. Drug Metab. Pharmacokinet., 9, 301 (1978)