(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,5S,13R,14S,17R)-14-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraen-10-yl]oxy}oxane-2-carboxylic acid

• ChemBase编号: 174807
• 分子式: C23H27NO9
• 平均质量: 461.46178
• 单一同位素质量: 461.16858145
• SMILES: c1(c2c3c(cc1)C[C@H]1[C@H]4[C@@]3([C@H]([C@H](C=C4)O)O2)CCN1C)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: O[C@@H]1[C@H](O)[C@@H](O[C@H]([C@H]1O)C(=O)O)Oc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@@H](C2)[C@@H]4C=C[C@@H]1O)C
• InChI: InChI=1S/C23H27NO9/c1-24-7-6-23-10-3-4-12(25)20(23)32-18-13(5-2-9(14(18)23)8-11(10)24)31-22-17(28)15(26)16(27)19(33-22)21(29)30/h2-5,10-12,15-17,19-20,22,25-28H,6-8H2,1H3,(H,29,30)/t10-,11-,12-,15-,16-,17+,19-,20-,22+,23-/m0/s1
• InChIKey: WAEXKFONHRHFBZ-MYIQFFIVSA-N

名称和登记号

名称

• IUPAC标准名: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,5S,13R,14S,17R)-14-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10,15-tetraen-10-yl]oxy}oxane-2-carboxylic acid
• IUPAC传统名: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,5S,13R,14S,17R)-14-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10,15-tetraen-10-yl]oxy}oxane-2-carboxylic acid
• 别名: (5α,6α)-7,8-Didehydro-4,5-epoxy-6-hydroxy-17-methylmorphinan-3-yl β-d-Glucopyranosiduronic Acid; 3-Glucuronosidomorphine; Morphine 3-O-Glucuronide; Morphine 3-β-D-Glucuronide

登记号

• CAS号: 20290-09-9
• PubChem SID: 164230717
• PubChem CID: 104879

理论计算性质

• Acid pKa: 2.673982
• 质子受体: 10
• 质子供体: 5
• LogD (pH = 5.5): -3.4821389
• LogD (pH = 7.4): -3.4876406
• Log P: -3.4819388
• 摩尔折射率: 112.1342 cm^3
• 极化性: 44.3441 Å^3
• 极化表面积: 149.15 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO; Water
• 外观: White Solid
• 熔点: >200°C (dec.)

安全信息

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

详细说明

Toronto Research Chemicals - M652300

A metabolite of Morphine. Analog of Morphine as molecular chameleon with unexpected lipophilicity.Controlled substance.

参考文献

• Christensen, C.B., et al.: Pharmacol. Toxicol., 60, 75 (1987)
• Coughtrie, M.W., et al.: Biochem. Pharmacol., 38, 3273 (1987)