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

• ChemBase ID: 169359
• 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[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)NC=O)O
• Canonical SMILES: O=CNc1cc(ccc1O)[C@@H](O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)CN[C@@H](Cc1ccc(cc1)OC)C
• InChI: InChI=1S/C25H32N2O10/c1-13(9-14-3-6-16(35-2)7-4-14)26-11-19(15-5-8-18(29)17(10-15)27-12-28)36-25-22(32)20(30)21(31)23(37-25)24(33)34/h3-8,10,12-13,19-23,25-26,29-32H,9,11H2,1-2H3,(H,27,28)(H,33,34)/t13-,19+,20+,21+,22-,23+,25-/m1/s1
• InChIKey: MHMCXDXGIWXFBN-KUNFAGBLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-[(1R)-1-(3-formamido-4-hydroxyphenyl)-2-{[(2R)-1-(4-methoxyphenyl)propan-2-yl]amino}ethoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-[(1R)-1-(3-formamido-4-hydroxyphenyl)-2-{[(2R)-1-(4-methoxyphenyl)propan-2-yl]amino}ethoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[3-(Formylamino)-4-hydroxyphenyl]-2-[[2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl β-D-Glucopyranosiduronic Acid; rac Formoterol 1'-O-β-D-Glucuronide

Database IDs

• CAS Number: 250336-07-3
• PubChem SID: 162263491
• PubChem CID: 71316928

CALCULATED PROPERTIES

• Acid pKa: 2.9445
• H Acceptors: 11
• H Donor: 7
• LogD (pH = 5.5): -1.8645988
• LogD (pH = 7.4): -1.8894384
• Log P: -1.8646444
• Molar Refractivity: 130.1522 cm^3
• Polarizability: 50.977837 Å^3
• Polar Surface Area: 187.04 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - F693415

A minor metabolite of Formoterol (F693400).

REFERENCES

• Rosenborg, J. et al.: Drug Metab. Disp., 27, 1104 (1999)