2-{2-[(1E)-[(pyridin-4-ylformamido)imino]methyl]phenoxy}acetic acid

• ChemBase ID: 179820
• Molecular Formular: C15H13N3O4
• Molecular Mass: 299.28142
• Monoisotopic Mass: 299.09060591
• SMILES: C(=O)(N/N=C/c1c(OCC(=O)O)cccc1)c1ccncc1
• Canonical SMILES: OC(=O)COc1ccccc1/C=N/NC(=O)c1ccncc1
• InChI: InChI=1S/C15H13N3O4/c19-14(20)10-22-13-4-2-1-3-12(13)9-17-18-15(21)11-5-7-16-8-6-11/h1-9H,10H2,(H,18,21)(H,19,20)/b17-9+
• InChIKey: MDFXJBQEWLCGHP-RQZCQDPDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{2-[(1E)-[(pyridin-4-ylformamido)imino]methyl]phenoxy}acetic acid
• IUPAC Traditional name: 2-{2-[(1E)-[(pyridin-4-ylformamido)imino]methyl]phenoxy}acetic acid
• Synonyms: Isonicophen; Phenoxalid; Aconiazide

Database IDs

• CAS Number: 13410-86-1
• PubChem SID: 164235730
• PubChem CID: 6433573

CALCULATED PROPERTIES

• Acid pKa: 3.4697962
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -1.1512307
• LogD (pH = 7.4): -2.3687108
• Log P: 0.60634327
• Molar Refractivity: 78.6264 cm^3
• Polarizability: 29.349548 Å^3
• Polar Surface Area: 100.88 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Inhibitor of mycolic acid synthesis and disruption of the cell wall in susceptible organisms; Interferes with several bacterial Enzyme systems

Product Information

• Description: Isomers(~5:1)
• Application(s): Antibacterial agent; Antiseptic; Tuberculostatic

REFERENCES

• Oeriu, S. et al., Rev. Chim., Acad. Repub. Pop. Roum., 1957, 2, 81; CA, 52, 14870, (synth, pharmacol)
• Dooley, K.L. et al., J. Am. Coll. Toxicol., 1993, 12, 329, (tox)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 113
• Peloquin, C.A. et al., Pharmacotherapy (Carlisle, Mass.), 1994, 14, 415, (pharmacokinet, human)