(2S,3S,4S,5R,6S)-6-{2-formamido-4-[(1R)-1-hydroxy-2-{[(2R)-1-(4-methoxyphenyl)propan-2-yl]amino}ethyl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 169213
• Molecular Formular: C25H32N2O10
• Molecular Mass: 520.52898
• Monoisotopic Mass: 520.20569523
• SMILES: c1c(c(cc(c1)[C@H](CN[C@@H](Cc1ccc(cc1)OC)C)O)NC=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: O=CNc1cc(ccc1O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)[C@H](CN[C@@H](Cc1ccc(cc1)OC)C)O
• InChI: InChI=1S/C25H32N2O10/c1-13(9-14-3-6-16(35-2)7-4-14)26-11-18(29)15-5-8-19(17(10-15)27-12-28)36-25-22(32)20(30)21(31)23(37-25)24(33)34/h3-8,10,12-13,18,20-23,25-26,29-32H,9,11H2,1-2H3,(H,27,28)(H,33,34)/t13-,18+,20+,21+,22-,23+,25-/m1/s1
• InChIKey: CHNNYXWDVZXHPK-WUTHJAFQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{2-formamido-4-[(1R)-1-hydroxy-2-{[(2R)-1-(4-methoxyphenyl)propan-2-yl]amino}ethyl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{2-formamido-4-[(1R)-1-hydroxy-2-{[(2R)-1-(4-methoxyphenyl)propan-2-yl]amino}ethyl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 2-(Formylamino)-4-[(1RS)-1-hydroxy-2-[[(1RS)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl β-D-Glucopyranosiduronic Acid; Formoterol O-β-D-Glucuronide (mixture of diastereomers)

Database IDs

• CAS Number: 615551-59-2
• PubChem SID: 162263345
• PubChem CID: 71316866

CALCULATED PROPERTIES

• Acid pKa: 2.7946548
• H Acceptors: 11
• H Donor: 7
• LogD (pH = 5.5): -2.3612583
• LogD (pH = 7.4): -2.3626835
• Log P: -2.360832
• Molar Refractivity: 129.8833 cm^3
• Polarizability: 50.975338 Å^3
• Polar Surface Area: 187.04 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - F693410

A major metabolite of Formoterol (F693400). Used in study of the effect of gender on the stereoselective metabolism and pharmacokinetics of Formoterol.

REFERENCES

• Zhang, M. et al.: Br. J. Clin. Pharmac., 54, 246 (2002)
• Yoshida, T., et al.: Pharmacometrics, 26, 811 (2002)
• Bartow, R.A., et al.: Drugs, 55, 303 (1998)