2-hydroxy-3-[(E)-2-{4-[(pyridin-2-yl)sulfamoyl]phenyl}diazen-1-yl]benzoic acid

• ChemBase ID: 177999
• Molecular Formular: C18H14N4O5S
• Molecular Mass: 398.39256
• Monoisotopic Mass: 398.06849057
• SMILES: c1(c(c(ccc1)C(=O)O)O)/N=N/c1ccc(cc1)S(=O)(=O)Nc1ncccc1
• Canonical SMILES: OC(=O)c1cccc(c1O)/N=N/c1ccc(cc1)S(=O)(=O)Nc1ccccn1
• InChI: InChI=1S/C18H14N4O5S/c23-17-14(18(24)25)4-3-5-15(17)21-20-12-7-9-13(10-8-12)28(26,27)22-16-6-1-2-11-19-16/h1-11,23H,(H,19,22)(H,24,25)/b21-20+
• InChIKey: RQKGJJSJEOATBZ-QZQOTICOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxy-3-[(E)-2-{4-[(pyridin-2-yl)sulfamoyl]phenyl}diazen-1-yl]benzoic acid
• IUPAC Traditional name: 2-hydroxy-3-[(E)-2-{4-[(pyridin-2-yl)sulfamoyl]phenyl}diazen-1-yl]benzoic acid
• Synonyms: 2-Hydroxy-3-[2-[4-[(2-pyridinylamino)sulfonyl]phenyl]diazenyl]benzoic Acid; 2-Hydroxy-3-[[4-[(2-pyridinylamino)sulfonyl]phenyl]azo]benzoic Acid; 3-[[p-(2-Pyridylsulfamoyl)phenyl]azo]salicylic Acid; Sulfasalazine Impurity F; Sulfasalazine 3-Isomer

Database IDs

• CAS Number: 66364-71-4
• PubChem SID: 164233909
• PubChem CID: 23344743

CALCULATED PROPERTIES

• Acid pKa: 3.326888
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): 2.0077825
• LogD (pH = 7.4): 0.25519457
• Log P: 3.9501588
• Molar Refractivity: 104.6029 cm^3
• Polarizability: 38.553684 Å^3
• Polar Surface Area: 141.31 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S699130

A positional isomeric impurity of Sulfasalazine (S699084).

REFERENCES

• Zalipsky, J.J. et al.: J. Pharmac. Sci., 67, 387 (1978)