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

• ChemBase编号: 164883
• 分子式: C31H37NO12
• 平均质量: 615.62498
• 单一同位素质量: 615.23157563
• SMILES: [C@H]12[C@H](C=C[C@@H]3[C@]41c1c(C[C@@H]3N(CC4)C)ccc(c1O2)OC)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)OC)OC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](O[C@H]2C=C[C@@H]3[C@@]45[C@H]2Oc2c5c(C[C@@H]3N(CC4)C)ccc2OC)[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C31H37NO12/c1-14(33)39-24-25(40-15(2)34)27(41-16(3)35)30(44-26(24)29(36)38-6)42-21-10-8-18-19-13-17-7-9-20(37-5)23-22(17)31(18,28(21)43-23)11-12-32(19)4/h7-10,18-19,21,24-28,30H,11-13H2,1-6H3/t18-,19-,21-,24-,25-,26-,27+,28-,30+,31-/m0/s1
• InChIKey: TWBYONVUJYLYAT-GMFRFZEASA-N

名称和登记号

名称

• IUPAC标准名: methyl (2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-{[(1S,5S,13R,14S,17R)-10-methoxy-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-14-yl]oxy}oxane-2-carboxylate
• IUPAC传统名: methyl (2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-{[(1S,5S,13R,14S,17R)-10-methoxy-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-14-yl]oxy}oxane-2-carboxylate
• 别名: 7,8-Didehydro-4,5α-epoxy-3-methoxy-17-methylmorphinan-6α-yl β-D-Glucopyranosiduronic Acid 2,3,4-Τriacetate Μethyl Εster; 7,8-Didehydro-4,5α-epoxy-6α-(β-D-glucopyranuronosyloxy)-3-methoxy-17-methyl-morphinan 2',3',4'-Triacetate Μethyl Εster; Codeine 6-(Tri-O-acetyl-6-methyl-β-D-glucopyranuronoside); Codeine β-D-Glucuronide Triacetate Methyl Ester

登记号

• CAS号: 20736-10-1
• PubChem SID: 162259017
• PubChem CID: 71314938

理论计算性质

• 质子受体: 9
• 质子供体: 0
• LogD (pH = 5.5): -1.924027
• LogD (pH = 7.4): -0.42965174
• Log P: 1.3616605
• 摩尔折射率: 149.109 cm^3
• 极化性: 59.869606 Å^3
• 极化表面积: 145.36 Å^2
• 可自由旋转的化学键: 11
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: Dichloromethane; Methanol
• 外观: Brown Solid

详细说明

Toronto Research Chemicals - C634120

A protected metabolite of Codeine (C634075).

参考文献

• Frances, B., et al.: J. Pharm. Exp. Ther., 25, 262 (1992)
• Osborne, R., et al.: Br. J. Clin. Pharm., 34, 130, (1992)