3-imino-6-oxocyclohexa-1,4-diene-1-carboxylic acid

• ChemBase ID: 171566
• Molecular Formular: C7H5NO3
• Molecular Mass: 151.1195
• Monoisotopic Mass: 151.02694303
• SMILES: C1=CC(=N)C=C(C1=O)C(=O)O
• Canonical SMILES: N=C1C=CC(=O)C(=C1)C(=O)O
• InChI: InChI=1S/C7H5NO3/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8H,(H,10,11)
• InChIKey: KXVMTWOQHOHKPO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-imino-6-oxocyclohexa-1,4-diene-1-carboxylic acid
• IUPAC Traditional name: 3-imino-6-oxocyclohexa-1,4-diene-1-carboxylic acid
• Synonyms: 5-Aminosalicylic Acid-quinoneimine; 3-Imino-6-oxo-1,4-cyclohexadiene-1-carboxylic Acid

Database IDs

• CAS Number: 143228-42-6
• PubChem SID: 164227476
• PubChem CID: 15731135

CALCULATED PROPERTIES

• Acid pKa: 3.3395963
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -2.0158014
• LogD (pH = 7.4): -2.078548
• Log P: -2.0160804
• Molar Refractivity: 49.5751 cm^3
• Polarizability: 13.809647 Å^3
• Polar Surface Area: 78.22 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - I425800

The oxidation product of the anti-inflammatory agent Mesalazine (M258100).

REFERENCES

• Palsmeier, R.K. et al.: Pharmac. Res., 9, 933 (1992)
• Liu, Z.C. et al.: Drug Metab. Disp., 23, 246 (1992)