(1R,3R,5S,8R)-8-{[4-(2H9)butoxyphenyl]methyl}-3-{[(2S)-3-hydroxy-2-phenylpropanoyl]oxy}-8-methyl-8-azabicyclo[3.2.1]octan-8-ium bromide

• ChemBase ID: 163134
• Molecular Formular: C28H38BrNO4
• Molecular Mass: 532.50962
• Monoisotopic Mass: 531.1984207
• SMILES: [Br-].[C@@H]12CC[C@@H]([N@+]1(Cc1ccc(cc1)OCCCC)C)C[C@@H](C2)OC(=O)[C@H](CO)c1ccccc1
• Canonical SMILES: CCCCOc1ccc(cc1)C[N@+]1(C)[C@@H]2CC[C@H]1C[C@H](C2)OC(=O)[C@@H](c1ccccc1)CO.[Br-]
• InChI: InChI=1S/C28H38NO4.BrH/c1-3-4-16-32-25-14-10-21(11-15-25)19-29(2)23-12-13-24(29)18-26(17-23)33-28(31)27(20-30)22-8-6-5-7-9-22;/h5-11,14-15,23-24,26-27,30H,3-4,12-13,16-20H2,1-2H3;1H/q+1;/p-1/t23-,24+,26+,27-,29-;/m1./s1
• InChIKey: JABDOYKGZCPHPX-AAXVZCMHSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3R,5S,8R)-8-{[4-(^2H₉)butoxyphenyl]methyl}-3-{[(2S)-3-hydroxy-2-phenylpropanoyl]oxy}-8-methyl-8-azabicyclo[3.2.1]octan-8-ium bromide
• IUPAC Traditional name: (1R,3R,5S,8R)-8-{[4-(^2H₉)butoxyphenyl]methyl}-3-{[(2S)-3-hydroxy-2-phenylpropanoyl]oxy}-8-methyl-8-azabicyclo[3.2.1]octan-8-ium bromide
• Synonyms: [3(S)-endo]-8-[(4-Butoxyphenyl-d9)methyl]-3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-azoniabicyclo[3.2.1]octane Bromide; (p-Butoxybenzyl-d9)hyoscyaminium Bromide; N-(Butoxybenzyl-d9)hyoscyamine Bromide; BHB-d9; Coliopan-d9; Butropium Bromide-d9

Database IDs

• PubChem SID: 162257269
• PubChem CID: 71314325

CALCULATED PROPERTIES

• Acid pKa: 15.144456
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.29960528
• LogD (pH = 7.4): 0.29960543
• Log P: 0.29960528
• Molar Refractivity: 141.6794 cm^3
• Polarizability: 51.445194 Å^3
• Polar Surface Area: 55.76 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - B690082

Anticholinergic. Antispasmodic.

REFERENCES

• Fujita, et al.: J. Labelled Compd., 9, 149 (1972)
• Tanaka, et al.: J. Pharm. Soc. Jpn., 92, 510 (1972)
• Kawamoto H., et al.: Arzneim.-Forsch., 35, 1475 (1972)