(2E)-but-2-enedioic acid; N-[2-hydroxy-5-(1-hydroxy-2-{[1-(4-methoxyphenyl)propan-2-yl]amino}ethyl)phenyl]formamide

• ChemBase ID: 169211
• Molecular Formular: C23H28N2O8
• Molecular Mass: 460.47702
• Monoisotopic Mass: 460.18456587
• SMILES: c1c(c(cc(c1)C(CNC(Cc1ccc(cc1)OC)C)O)NC=O)O.C(=C\C(=O)O)/C(=O)O
• Canonical SMILES: OC(=O)/C=C/C(=O)O.O=CNc1cc(ccc1O)C(CNC(Cc1ccc(cc1)OC)C)O
• InChI: InChI=1S/C19H24N2O4.C4H4O4/c1-13(9-14-3-6-16(25-2)7-4-14)20-11-19(24)15-5-8-18(23)17(10-15)21-12-22;5-3(6)1-2-4(7)8/h3-8,10,12-13,19-20,23-24H,9,11H2,1-2H3,(H,21,22);1-2H,(H,5,6)(H,7,8)/b;2-1+
• InChIKey: ZDUPYZMAPCZGJO-WLHGVMLRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-but-2-enedioic acid; N-[2-hydroxy-5-(1-hydroxy-2-{[1-(4-methoxyphenyl)propan-2-yl]amino}ethyl)phenyl]formamide
• IUPAC Traditional name: formoterol; fumaric acid
• Synonyms: N-[2-Hydroxy-5-[1-hydroxy-2-[[2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]-formamide (2E)-2-Butenedioate Salt; Formoterol Fumarate(Mixture of Diastereomers)

Database IDs

• CAS Number: 169375-55-7
• PubChem SID: 162263343
• PubChem CID: 9912089

CALCULATED PROPERTIES

• Acid pKa: 8.607353
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -1.1008605
• LogD (pH = 7.4): 0.03789571
• Log P: 1.0566727
• Molar Refractivity: 97.8715 cm^3
• Polarizability: 37.3542 Å^3
• Polar Surface Area: 90.82 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F693401

Formoterol fumarate (mixture of diastereomers) is an impurity of Formoterol fumarate dihydrate (F693400).

REFERENCES

• Yoshida, T., et al.: Pharmacometrics, 26, 811 (1983)
• Bartow, R.A., et al.: Drugs, 55, 303 (1983)