(2S,3S,4S,5R)-6-[1-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)-2-{[2-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)-2-hydroxyethyl]amino}ethoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 175038
• Molecular Formular: C28H33F2NO10
• Molecular Mass: 581.5591264
• Monoisotopic Mass: 581.2072527
• SMILES: c1cc(cc2c1OC(CC2)C(CNCC(C1CCc2c(O1)ccc(c2)F)O)OC1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)F
• Canonical SMILES: Fc1ccc2c(c1)CCC(O2)C(CNCC(C1CCc2c(O1)ccc(c2)F)OC1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)O
• InChI: InChI=1S/C28H33F2NO10/c29-15-3-7-18-13(9-15)1-5-20(38-18)17(32)11-31-12-22(21-6-2-14-10-16(30)4-8-19(14)39-21)40-28-25(35)23(33)24(34)26(41-28)27(36)37/h3-4,7-10,17,20-26,28,31-35H,1-2,5-6,11-12H2,(H,36,37)/t17?,20?,21?,22?,23-,24-,25+,26-,28?/m0/s1
• InChIKey: UCVWRMDTTYGOAE-JASWYMMZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R)-6-[1-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)-2-{[2-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)-2-hydroxyethyl]amino}ethoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R)-6-[1-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)-2-{[2-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)-2-hydroxyethyl]amino}ethoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 6-Fluoro-3,4-dihydro-2H-1-benzopyran-2-yl]-2-[2-[6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl]-2-hydroxyethyl]amino]ethyl β-D-Glucopyranosiduronic Acid; Nebivolol O-β-D-Glucuronide(Mixture of 4 Diastereomers)

Database IDs

• PubChem SID: 164230948
• PubChem CID: 71750961

CALCULATED PROPERTIES

• Acid pKa: 3.065775
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -0.7149363
• LogD (pH = 7.4): -0.72751987
• Log P: -0.71442163
• Molar Refractivity: 135.5979 cm^3
• Polarizability: 53.967106 Å^3
• Polar Surface Area: 167.17 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - N387880

Nebivolol (N387896) metabolite.