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

• ChemBase ID: 161156
• Molecular Formular: C42H50N2O15
• Molecular Mass: 822.8508
• Monoisotopic Mass: 822.32111891
• SMILES: c1(ccc(cc1)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)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]2O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]2O)O)O)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C42H50N2O15/c1-22-28-20-27(57-42-36(50)32(46)34(48)38(59-42)40(53)54)14-15-29(28)44(21-23-6-10-25(11-7-23)55-19-18-43-16-4-2-3-5-17-43)30(22)24-8-12-26(13-9-24)56-41-35(49)31(45)33(47)37(58-41)39(51)52/h6-15,20,31-38,41-42,45-50H,2-5,16-19,21H2,1H3,(H,51,52)(H,53,54)/t31-,32-,33-,34-,35+,36+,37-,38-,41+,42+/m0/s1
• InChIKey: FMPLVZPGUJCCCC-FOIJVJNNSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 328933-67-1
• PubChem SID: 162255291
• PubChem CID: 9875830

CALCULATED PROPERTIES

• Rotatable Bonds: 13
• Lipinski's Rule of Five: false
• Acid pKa: 2.794281
• H Acceptors: 16
• H Donor: 8
• LogD (pH = 5.5): -2.0622382
• LogD (pH = 7.4): -3.3832798
• Log P: -0.23825794
• Molar Refractivity: 205.9194 cm^3
• Polarizability: 84.005196 Å^3
• Polar Surface Area: 250.3 Å^2

DETAILS

Toronto Research Chemicals - B129265

A metabolite of Bazedoxifene (B129250).

REFERENCES

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