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

• ChemBase ID: 165586
• Molecular Formular: C24H30N2O8
• Molecular Mass: 474.5036
• Monoisotopic Mass: 474.20021593
• SMILES: c1c(c(cc(c1)C(CNC(Cc1ccc(cc1)OC)C)O)NC(=O)C)O.C(=C\C(=O)O)/C(=O)O
• Canonical SMILES: OC(=O)/C=C/C(=O)O.COc1ccc(cc1)CC(NCC(c1ccc(c(c1)NC(=O)C)O)O)C
• InChI: InChI=1S/C20H26N2O4.C4H4O4/c1-13(10-15-4-7-17(26-3)8-5-15)21-12-20(25)16-6-9-19(24)18(11-16)22-14(2)23;5-3(6)1-2-4(7)8/h4-9,11,13,20-21,24-25H,10,12H2,1-3H3,(H,22,23);1-2H,(H,5,6)(H,7,8)/b;2-1+
• InChIKey: FAPZFUZYRHHHLH-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]acetamide
• IUPAC Traditional name: N-[2-hydroxy-5-(1-hydroxy-2-{[1-(4-methoxyphenyl)propan-2-yl]amino}ethyl)phenyl]acetamide; fumaric acid
• Synonyms: N-[2-Hydroxy-5-[1-hydroxy-2-[[2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]acetamide (2E)-2-Butenedioate Salt; N-Deformyl-N-acetyl Formoterol Fumarate (Mixture of Diastereomers)

Database IDs

• PubChem SID: 162259719
• PubChem CID: 71315284

CALCULATED PROPERTIES

• Acid pKa: 8.595098
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -1.050977
• LogD (pH = 7.4): 0.092323594
• Log P: 1.1029431
• Molar Refractivity: 102.362 cm^3
• Polarizability: 39.194225 Å^3
• Polar Surface Area: 90.82 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D229065

N-Deformyl-N-acetyl Formoterol fumarate is an impurity of Formoterol fumarate dihydrate (F693400).

REFERENCES

• van Den Berg, B., et al.: Ther. Drug Monit., 16, 196 (1994)
• Bartow, R., et al.: Drug, 1998, 55, 303 (1994)
• Benhamou, D., et al.: Respir. Med., 95, 817 (1994)