(1R,2S,8S,10S,11S,13S,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-13-(2H3)methyl-2,15-dimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-diene-14-carboxylic acid

• ChemBase编号: 169298
• 分子式: C21H26F2O5
• 平均质量: 396.4249464
• 单一同位素质量: 396.17483037
• SMILES: C1=CC(=O)C=C2[C@]1([C@@]1([C@@H](C[C@@H]2F)[C@H]2[C@](C[C@@H]1O)([C@@]([C@H](C2)C)(O)C(=O)O)C)F)C
• Canonical SMILES: O=C1C=C[C@]2(C(=C1)[C@@H](F)C[C@@H]1[C@]2(F)[C@@H](O)C[C@]2([C@H]1C[C@@H]([C@]2(O)C(=O)O)C)C)C
• InChI: InChI=1S/C21H26F2O5/c1-10-6-12-13-8-15(22)14-7-11(24)4-5-18(14,2)20(13,23)16(25)9-19(12,3)21(10,28)17(26)27/h4-5,7,10,12-13,15-16,25,28H,6,8-9H2,1-3H3,(H,26,27)/t10-,12-,13-,15-,16-,18-,19-,20-,21-/m0/s1
• InChIKey: QSVBUQTYFQFEHC-AUWFFNLJSA-N

名称和登记号

名称

• IUPAC标准名: (1R,2S,8S,10S,11S,13S,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-13-(^2H₃)methyl-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-14-carboxylic acid
• IUPAC传统名: (1R,2S,8S,10S,11S,13S,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-13-(^2H₃)methyl-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-14-carboxylic acid
• 别名: (6α,11β,16α,17α)-6,9-Difluoro-11,17-dihydroxy-16-(methyl-d3)-3-oxo-androsta-1,4-diene-17-carboxylic Acid; 6α,9α-Difluoro-11β,17α-dihydroxy-16α-(methyl-d3)pregna-3-oxo-1,4-diene-17β-carboxylic Acid; Fluticasone-d3 17β-Carboxylic Acid

登记号

• PubChem SID: 162263430
• PubChem CID: 71316899

理论计算性质

• Acid pKa: 4.3641305
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): 0.66469973
• LogD (pH = 7.4): -1.0859193
• Log P: 1.8294729
• 摩尔折射率: 97.063 cm^3
• 极化性: 37.41019 Å^3
• 极化表面积: 94.83 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Chloroform; Dichloromethane; DMF; Methanol
• 外观: Off-White to Light-Yellow Solid
• 熔点: 303-305°C

详细说明

Toronto Research Chemicals - F599492

The labelled major metabolite of Fluticasone. Anti-inflammatory agent.

参考文献

• Meltzer, E.O., et al.: J. Allergy Clin. Immunol., 86, 221 (1990)
• Mitchison, H.C., et al.: Gut, 32, 260 (1990)
• Ueno, H., et al.: J. Med. Chem., 34, 2468 (1990)
• Rachwal, S., et al.: Steroids, 63, 193 (1990)
• Phillipps, G.H., et al.: J. Med. Chem., 37, 37