2,3-dimethoxy-6-[(1E)-[(pyridin-4-ylformamido)imino]methyl]benzoic acid

• ChemBase ID: 179802
• Molecular Formular: C16H15N3O5
• Molecular Mass: 329.3074
• Monoisotopic Mass: 329.1011706
• SMILES: c1(c(c(ccc1/C=N/NC(=O)c1ccncc1)OC)OC)C(=O)O
• Canonical SMILES: COc1c(OC)ccc(c1C(=O)O)/C=N/NC(=O)c1ccncc1
• InChI: InChI=1S/C16H15N3O5/c1-23-12-4-3-11(13(16(21)22)14(12)24-2)9-18-19-15(20)10-5-7-17-8-6-10/h3-9H,1-2H3,(H,19,20)(H,21,22)/b18-9+
• InChIKey: HSYFNANHKYNZNI-GIJQJNRQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,3-dimethoxy-6-[(1E)-[(pyridin-4-ylformamido)imino]methyl]benzoic acid
• IUPAC Traditional name: 2,3-dimethoxy-6-[(1E)-[(pyridin-4-ylformamido)imino]methyl]benzoic acid
• Synonyms: Carboxyverazide; Saluside; Saluzid; Opiniazide

Database IDs

• CAS Number: 2779-55-7
• PubChem SID: 164235712
• PubChem CID: 6871212

CALCULATED PROPERTIES

• Acid pKa: 2.6482072
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -1.454981
• LogD (pH = 7.4): -2.3976548
• Log P: 0.48018828
• Molar Refractivity: 86.2612 cm^3
• Polarizability: 31.874949 Å^3
• Polar Surface Area: 110.11 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
• Application(s): Antibacterial (tuberculostatic) agent; Antiseptic

REFERENCES

• Japan. Pat., 1957, Shionogi, 57 8 078; CA, 52, 13805c, (synth, pharmacol)
• Veis, R.A., Antibiotiki (Moscow), 1969, 14, 1016; CA, 72, 53471v, (pharmacol)
• Akhundov, R.A., CA, 1977, 86, 50678y; 115162x, (pharmacol, tox)