(2S,3S,4S,5R,6S)-6-[4-(2-{[2-(3,5-dihydroxyphenyl)-2-hydroxyethyl]amino}propyl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 168909
• Molecular Formular: C23H29NO10
• Molecular Mass: 479.47706
• Monoisotopic Mass: 479.17914613
• SMILES: c1c(cc(cc1O)C(CNC(Cc1ccc(cc1)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)C)O)O
• Canonical SMILES: CC(Cc1ccc(cc1)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)NCC(c1cc(O)cc(c1)O)O
• InChI: InChI=1S/C23H29NO10/c1-11(24-10-17(27)13-7-14(25)9-15(26)8-13)6-12-2-4-16(5-3-12)33-23-20(30)18(28)19(29)21(34-23)22(31)32/h2-5,7-9,11,17-21,23-30H,6,10H2,1H3,(H,31,32)/t11?,17?,18-,19-,20+,21-,23+/m0/s1
• InChIKey: VPLCRUFRMASDFW-IWKWYPLWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[4-(2-{[2-(3,5-dihydroxyphenyl)-2-hydroxyethyl]amino}propyl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-[4-(2-{[2-(3,5-dihydroxyphenyl)-2-hydroxyethyl]amino}propyl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 4-[2-[[2-(3,5-Dihydroxyphenyl)-2-hydroxyethyl]amino]propyl]phenyl β-D-Glucopyranosiduronic Acid; Fenoterol O-β-D-Glucuronide

Database IDs

• CAS Number: 61046-78-4
• PubChem SID: 162263041
• PubChem CID: 71316731

CALCULATED PROPERTIES

• Acid pKa: 2.9798524
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -2.0002396
• LogD (pH = 7.4): -2.013227
• Log P: -1.9998893
• Molar Refractivity: 117.0094 cm^3
• Polarizability: 46.630108 Å^3
• Polar Surface Area: 189.17 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - F248860

A metabolite of Fenoterol (F248850).

REFERENCES

• Koster, A.S. et al.: Biochem. Pharmacol., 35, 1981 (1986)
• Pook, K.H. et al.: J. Pharmac. Sci., 65, 1513 (1986)