4-amino(2H4)benzene-1-sulfonamide

• ChemBase ID: 177920
• Molecular Formular: C6H8N2O2S
• Molecular Mass: 172.20492
• Monoisotopic Mass: 172.03064851
• SMILES: c1c(ccc(c1)S(=O)(=O)N)N
• Canonical SMILES: Nc1ccc(cc1)S(=O)(=O)N
• InChI: InChI=1S/C6H8N2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H2,8,9,10)
• InChIKey: FDDDEECHVMSUSB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino(^2H₄)benzene-1-sulfonamide
• IUPAC Traditional name: 4-amino(^2H₄)benzenesulfonamide
• Synonyms: Sulfanilamide-d4; 4-Aminophenylsulfonamide-d4; 4-Sulfamoylaniline-d4; A-349-d4; Albexan-d4; Albosal-d4; Ambeside-d4; Antistrept-d4; Astreptine-d4; Astrocid-d4; Bacteramid-d4; Bactesid-d4; Collomide-d4; Deseptyl-d4; Dipron-d4; Ergaseptine-d4; Erysipan-d4; p-Sulfamoylaniline-d4; Sulphanilamide-d4; p-Aminobenzenesulfonamide-d4; 4-(Aminosulfonyl)aniline-d4

Database IDs

• CAS Number: 77435-46-2
• PubChem SID: 164233830
• PubChem CID: 12208581

CALCULATED PROPERTIES

• Acid pKa: 10.990055
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.2499021
• LogD (pH = 7.4): -0.2497514
• Log P: -0.24964938
• Molar Refractivity: 42.9163 cm^3
• Polarizability: 16.806332 Å^3
• Polar Surface Area: 86.18 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S689102

The active labelled metabolite of the antibacterial dye, Sulfamidochrysoidine. Inhibits folic acid synthesis in prokaryotes. Antibacterial.

REFERENCES

• Colebrook, L., et al.: Lancet, 233, 1291 (1937)
• Dye, C., et al.: Nat. Rev. Microbiol., 7, 81 (1937)
• Isik, S., et al.: Bioorg. Med. Chem., 17, 1158 (1937)