4-({2-[(4-carboxyphenyl)amino]ethyl}amino)benzoic acid

• ChemBase ID: 168559
• Molecular Formular: C16H16N2O4
• Molecular Mass: 300.30924
• Monoisotopic Mass: 300.111007
• SMILES: c1c(ccc(c1)NCCNc1ccc(cc1)C(=O)O)C(=O)O
• Canonical SMILES: OC(=O)c1ccc(cc1)NCCNc1ccc(cc1)C(=O)O
• InChI: InChI=1S/C16H16N2O4/c19-15(20)11-1-5-13(6-2-11)17-9-10-18-14-7-3-12(4-8-14)16(21)22/h1-8,17-18H,9-10H2,(H,19,20)(H,21,22)
• InChIKey: PLRTXWVDXUGELT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-({2-[(4-carboxyphenyl)amino]ethyl}amino)benzoic acid
• IUPAC Traditional name: 4-({2-[(4-carboxyphenyl)amino]ethyl}amino)benzoic acid
• Synonyms: 4,4’-(1,2-Ethanediyldiimino)bisbenzoic Acid; 4,4'-(Ethylenediimino)dibenzoic Acid

Database IDs

• CAS Number: 95627-01-3
• PubChem SID: 162262691
• PubChem CID: 53434978

CALCULATED PROPERTIES

• Acid pKa: 4.494128
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 0.33775485
• LogD (pH = 7.4): -3.1984713
• Log P: 1.7206609
• Molar Refractivity: 85.047 cm^3
• Polarizability: 30.563866 Å^3
• Polar Surface Area: 98.66 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E917810

A N,N'-diarylethylenediamine derivative as models of tetrahydrofolic acid in nonenzymic reactions.

REFERENCES

• Bodor, et al.: Pharmacol. Therap., 19(3)
• 337, 1983,