(2S,3S,4S,5R,6S)-6-(1-{[4-cyano-3-(trifluoromethyl)phenyl]carbamoyl}-2-[4-fluoro(2H4)benzenesulfonyl]-1-methylethoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 162038
• Molecular Formular: C24H22F4N2O10S
• Molecular Mass: 606.4974928
• Monoisotopic Mass: 606.09312879
• SMILES: c1c(c(ccc1NC(=O)C(CS(=O)(=O)c1ccc(cc1)F)(O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)C)C#N)C(F)(F)F
• Canonical SMILES: N#Cc1ccc(cc1C(F)(F)F)NC(=O)C(CS(=O)(=O)c1ccc(cc1)F)(O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)C
• InChI: InChI=1S/C24H22F4N2O10S/c1-23(10-41(37,38)14-6-3-12(25)4-7-14,40-21-18(33)16(31)17(32)19(39-21)20(34)35)22(36)30-13-5-2-11(9-29)15(8-13)24(26,27)28/h2-8,16-19,21,31-33H,10H2,1H3,(H,30,36)(H,34,35)/t16-,17-,18+,19-,21-,23?/m0/s1
• InChIKey: OYKHNYWINRLUAP-CQNXPSKISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-(1-{[4-cyano-3-(trifluoromethyl)phenyl]carbamoyl}-2-[4-fluoro(^2H₄)benzenesulfonyl]-1-methylethoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-(1-{[4-cyano-3-(trifluoromethyl)phenyl]carbamoyl}-2-[4-fluoro(^2H₄)benzenesulfonyl]-1-methylethoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 2-[[4-Cyano-3-(trifluoromethyl)phenyl]amino]-1-[[(4-fluorophenyl)sulfonyl]methyl]-1-methyl-2-oxoethyl β-D-Glucopyranosiduronic Acid; Bicalutamide Glucuronide; Casodex Glucuronide; Bicalutamide O-β-D-Glucuronide

Database IDs

• CAS Number: 151262-59-8
• PubChem SID: 162256173
• PubChem CID: 71313965

CALCULATED PROPERTIES

• Acid pKa: 2.7488427
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -1.4262686
• LogD (pH = 7.4): -2.2391179
• Log P: 1.2587345
• Molar Refractivity: 128.8702 cm^3
• Polarizability: 50.00692 Å^3
• Polar Surface Area: 203.48 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - B382015

A metabolite of the non-steroidal peripherally active antiandrogen Bicalutamide (B382000).

REFERENCES

• McKillop, D. et al.: Xenobiot., 23, 1241 (1993)
• McKillop, D. et al.: Xenobiotica, 25, 623 (1993)