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

• ChemBase ID: 163733
• Molecular Formular: C27H24N4O9
• Molecular Mass: 548.50086
• Monoisotopic Mass: 548.15432837
• SMILES: c1cc(c(cc1/N=N/c1ccc(cc1)C(=O)NCCC(=O)O)C(=O)O)Oc1ccc(cc1)C(=O)NCCC(=O)O
• Canonical SMILES: OC(=O)CCNC(=O)c1ccc(cc1)/N=N/c1ccc(c(c1)C(=O)O)Oc1ccc(cc1)C(=O)NCCC(=O)O
• InChI: InChI=1S/C27H24N4O9/c32-23(33)11-13-28-25(36)16-1-5-18(6-2-16)30-31-19-7-10-22(21(15-19)27(38)39)40-20-8-3-17(4-9-20)26(37)29-14-12-24(34)35/h1-10,15H,11-14H2,(H,28,36)(H,29,37)(H,32,33)(H,34,35)(H,38,39)/b31-30+
• InChIKey: BXJNXRKWSCKIFA-NVQSTNCTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{4-[(2-carboxyethyl)carbamoyl]phenoxy}-5-[(E)-2-{4-[(2-carboxyethyl)carbamoyl]phenyl}diazen-1-yl]benzoic acid
• IUPAC Traditional name: 2-{4-[(2-carboxyethyl)carbamoyl]phenoxy}-5-[(E)-2-{4-[(2-carboxyethyl)carbamoyl]phenyl}diazen-1-yl]benzoic acid
• Synonyms: 5-[(1E)-2-[4-[[(2-carboxyethyl)amino]carbonyl]phenyl]diazenyl]-2-[[(2-carboxyethyl)amino]carbonyl]phenoxy]benzoic Acid; (E)-2-[4-(2-Carboxyethylcarbamoyl)phenoxy]-5-[[4-(2-carboxyethylcarbamoyl)]phenylazo]benzoic Acid; Balsalazide USP Impurity 4; 2-O-[4-[[(2-carboxyethyl)amino]carbonyl]phenyl] Balsalazide

Database IDs

• PubChem SID: 162257868
• PubChem CID: 71314535

CALCULATED PROPERTIES

• Acid pKa: 3.2312121
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -2.1309958
• LogD (pH = 7.4): -6.699179
• Log P: 3.1156344
• Molar Refractivity: 143.3922 cm^3
• Polarizability: 52.161514 Å^3
• Polar Surface Area: 204.05 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C178010

An impurity of the anti-inflammatory drug Balsalazide (B116300).