5-[(E)-2-{4-[(2-carboxyethyl)carbamoyl]phenyl}diazen-1-yl]-2-hydroxy(2H3)benzoic acid

• ChemBase ID: 161106
• Molecular Formular: C17H15N3O6
• Molecular Mass: 357.3175
• Monoisotopic Mass: 357.09608522
• SMILES: c1cc(c(cc1/N=N/c1ccc(cc1)C(=O)NCCC(=O)O)C(=O)O)O
• Canonical SMILES: OC(=O)CCNC(=O)c1ccc(cc1)/N=N/c1ccc(c(c1)C(=O)O)O
• InChI: InChI=1S/C17H15N3O6/c21-14-6-5-12(9-13(14)17(25)26)20-19-11-3-1-10(2-4-11)16(24)18-8-7-15(22)23/h1-6,9,21H,7-8H2,(H,18,24)(H,22,23)(H,25,26)/b20-19+
• InChIKey: IPOKCKJONYRRHP-FMQUCBEESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(E)-2-{4-[(2-carboxyethyl)carbamoyl]phenyl}diazen-1-yl]-2-hydroxy(^2H₃)benzoic acid
• IUPAC Traditional name: 5-[(E)-2-{4-[(2-carboxyethyl)carbamoyl]phenyl}diazen-1-yl]-2-hydroxy(^2H₃)benzoic acid
• Synonyms: 5-[(1E)-2-[4-[[(2-Carboxyethyl)amino]carbonyl]phenyl]diazenyl]-2-hydroxy-benzoic Acid-d3; Balsalazido-d3; Balsalazidum-d3; Colazide-d3; Balsalazide-d3

Database IDs

• PubChem SID: 162255241
• PubChem CID: 71313614

CALCULATED PROPERTIES

• Rotatable Bonds: 7
• Lipinski's Rule of Five: true
• Acid pKa: 3.0649273
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.0041051
• LogD (pH = 7.4): -3.6215541
• Log P: 3.1724694
• Molar Refractivity: 94.3732 cm^3
• Polarizability: 33.546432 Å^3
• Polar Surface Area: 148.65 Å^2

DETAILS

Toronto Research Chemicals - B116302

Labelled Balsalazide. An analogue of Sulfasalazine (S699084). A prodrug of 5-aminosalicylic acid where carrier molecule is 4-aminobenzoyl-β-alanine. Anti-inflammatory (gastrointestinal).

REFERENCES

• Prakash, A., et al.: Drugs, 56, 83 (1998)
• Coyne, C., et al.: Mol. Biol. Cell, 13, 3218 (1998)
• Willemsen, L., et al.: Clin. Exp. Immunol., 142, 275 (1998)