(1R)-1-[(2S)-6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl]-2-{[(2R)-2-[(2S)-6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl]-2-hydroxyethyl]amino}ethan-1-ol

• ChemBase ID: 175048
• Molecular Formular: C22H25F2NO4
• Molecular Mass: 405.4350064
• Monoisotopic Mass: 405.17516473
• SMILES: c1cc(cc2c1O[C@@H](CC2)[C@@H](CNC[C@H]([C@@H]1CCc2c(O1)ccc(c2)F)O)O)F
• Canonical SMILES: O[C@@H]([C@@H]1CCc2c(O1)ccc(c2)F)CNC[C@H]([C@@H]1CCc2c(O1)ccc(c2)F)O
• InChI: InChI=1S/C22H25F2NO4/c23-15-3-7-19-13(9-15)1-5-21(28-19)17(26)11-25-12-18(27)22-6-2-14-10-16(24)4-8-20(14)29-22/h3-4,7-10,17-18,21-22,25-27H,1-2,5-6,11-12H2/t17-,18-,21+,22+/m1/s1
• InChIKey: KOHIRBRYDXPAMZ-UBBRYJJRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R)-1-[(2S)-6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl]-2-{[(2R)-2-[(2S)-6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl]-2-hydroxyethyl]amino}ethan-1-ol
• IUPAC Traditional name: nuβ
• Synonyms: [2S-[2R*[S*[S*(R*)]]]]-α,α'-[Iminobis(methylene)]bis[6-fluoro-3,4-dihydro-2H-1-benzopyran-2-methanol; R 65260; (S,R,R,S)-Nebivolol

Database IDs

• CAS Number: 119365-23-0
• PubChem SID: 164230958
• PubChem CID: 14577197

CALCULATED PROPERTIES

• Acid pKa: 13.520145
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 0.19658114
• LogD (pH = 7.4): 1.7054241
• Log P: 3.208403
• Molar Refractivity: 103.3172 cm^3
• Polarizability: 40.23752 Å^3
• Polar Surface Area: 70.95 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N387910

The S,R,R,S-enantiomer of Nebivolol (N387900), a metabolite in vitro which acts as a β-adrenergic blocker.

REFERENCES

• Pauwels, P.J., et al.: Mol. Pharmacol., 34, 843 (1988)