1-[2-(4-{[5-hydroxy-2-(4-hydroxyphenyl)-3-methyl-1H-indol-1-yl]methyl}phenoxy)ethyl]azepan-1-ium-1-olate

• ChemBase ID: 161159
• Molecular Formular: C30H34N2O4
• Molecular Mass: 486.60196
• Monoisotopic Mass: 486.25185758
• SMILES: c1(ccc(cc1)O)c1n(Cc2ccc(cc2)OCC[N+]2(CCCCCC2)[O-])c2ccc(cc2c1C)O
• Canonical SMILES: Oc1ccc2c(c1)c(C)c(n2Cc1ccc(cc1)OCC[N+]1([O-])CCCCCC1)c1ccc(cc1)O
• InChI: InChI=1S/C30H34N2O4/c1-22-28-20-26(34)12-15-29(28)31(30(22)24-8-10-25(33)11-9-24)21-23-6-13-27(14-7-23)36-19-18-32(35)16-4-2-3-5-17-32/h6-15,20,33-34H,2-5,16-19,21H2,1H3
• InChIKey: CFBANWAZVCOMGU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[2-(4-{[5-hydroxy-2-(4-hydroxyphenyl)-3-methyl-1H-indol-1-yl]methyl}phenoxy)ethyl]azepan-1-ium-1-olate
• IUPAC Traditional name: 1-[2-(4-{[5-hydroxy-2-(4-hydroxyphenyl)-3-methylindol-1-yl]methyl}phenoxy)ethyl]azepan-1-ium-1-olate
• Synonyms: 1-[[4-[2-(Hexahydro-1-oxido-1H-azepin-1-yl)ethoxy]phenyl]methyl]-2-(4-hydroxyphenyl)-3-methyl-1H-indol-5-ol; Bazedoxifene N-Oxide

Database IDs

• CAS Number: 1174289-22-5
• PubChem SID: 162255294
• PubChem CID: 59499290

CALCULATED PROPERTIES

• Acid pKa: 9.424062
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 5.525108
• LogD (pH = 7.4): 5.521135
• Log P: 5.525207
• Molar Refractivity: 143.9407 cm^3
• Polarizability: 57.173676 Å^3
• Polar Surface Area: 81.5 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - B129280

Bazedoxifene N-Oxide is a metabolite of the selective estrogen receptor modulator, Bazedoxifene (B129250)

REFERENCES

• Chandrasekaran, A. et al.: Drug Metab. Dispos., 37, 1219 (2009)