3-[(4-sulfamoylphenyl)carbamoyl]propanoic acid

• ChemBase ID: 179791
• Molecular Formular: C10H12N2O5S
• Molecular Mass: 272.27768
• Monoisotopic Mass: 272.04669249
• SMILES: S(=O)(=O)(c1ccc(NC(=O)CCC(=O)O)cc1)N
• Canonical SMILES: O=C(Nc1ccc(cc1)S(=O)(=O)N)CCC(=O)O
• InChI: InChI=1S/C10H12N2O5S/c11-18(16,17)8-3-1-7(2-4-8)12-9(13)5-6-10(14)15/h1-4H,5-6H2,(H,12,13)(H,14,15)(H2,11,16,17)
• InChIKey: RXXXPZYBZLDQKP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(4-sulfamoylphenyl)carbamoyl]propanoic acid
• IUPAC Traditional name: 3-[(4-sulfamoylphenyl)carbamoyl]propanoic acid
• Synonyms: Succinylsulfanilamide; Ambesid; Anaseptil-Colirio; Derganil; Erysipan-soluble; Sulfasuccinamide

Database IDs

• CAS Number: 3563-14-2
• PubChem SID: 164235701
• PubChem CID: 60582

CALCULATED PROPERTIES

• Acid pKa: 3.3723063
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.4721885
• LogD (pH = 7.4): -3.7684138
• Log P: -0.3581503
• Molar Refractivity: 63.9722 cm^3
• Polarizability: 24.855154 Å^3
• Polar Surface Area: 126.56 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Folic acid biosynthesis antagonist

Product Information

• Application(s): Antibacterial agent; Antiseptic

REFERENCES

• Fr. Pat., 1951, 992 364; CA, 51, 3663e, (synth, pharmacol)
• Kho, B.T. et al., J. Pharm. Sci., 1963, 52, 404, (tlc)