(2S,3S,4S,5R,6S)-6-{[1-({4-[2-(azepan-1-yl)ethoxy]phenyl}methyl)-2-(4-hydroxyphenyl)-3-methyl-1H-indol-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 161158
• Molecular Formular: C36H42N2O9
• Molecular Mass: 646.72668
• Monoisotopic Mass: 646.28903093
• SMILES: c1(ccc(cc1)O)c1n(Cc2ccc(cc2)OCCN2CCCCCC2)c2ccc(cc2c1C)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](Oc2ccc3c(c2)c(C)c(n3Cc2ccc(cc2)OCCN2CCCCCC2)c2ccc(cc2)O)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C36H42N2O9/c1-22-28-20-27(46-36-33(42)31(40)32(41)34(47-36)35(43)44)14-15-29(28)38(30(22)24-8-10-25(39)11-9-24)21-23-6-12-26(13-7-23)45-19-18-37-16-4-2-3-5-17-37/h6-15,20,31-34,36,39-42H,2-5,16-19,21H2,1H3,(H,43,44)/t31-,32-,33+,34-,36+/m0/s1
• InChIKey: PAAXRVKIJQNQMY-VNOFEJHXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[1-({4-[2-(azepan-1-yl)ethoxy]phenyl}methyl)-2-(4-hydroxyphenyl)-3-methyl-1H-indol-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{[1-({4-[2-(azepan-1-yl)ethoxy]phenyl}methyl)-2-(4-hydroxyphenyl)-3-methylindol-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[[4-[2-(Hexahydro-1H-azepin-1-yl)ethoxy]phenyl]methyl]-2-(4-hydroxyphenyl)-3-methyl-1H-indol-5-yl β-D-Glucopyranosiduronic Acid; Bazedoxifene 5-β-D-Glucuronide

Database IDs

• CAS Number: 328933-56-8
• PubChem SID: 162255293
• PubChem CID: 9895767

CALCULATED PROPERTIES

• Acid pKa: 3.0481045
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): 1.9697088
• LogD (pH = 7.4): 1.9659389
• Log P: 1.9704382
• Molar Refractivity: 173.9076 cm^3
• Polarizability: 70.44556 Å^3
• Polar Surface Area: 154.08 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - B129275

A metabolite of Bazedoxifene (B129250).

REFERENCES

• Kemp, D., et al.: Drug Metab. Dispos., 30, 694 (2002)
• Komm, B., et al.: Endocrinology, 146, 3999 (2002)