2-chloro-4-[(furan-2-ylmethyl)amino]-5-sulfamoylbenzoic acid

• ChemBase ID: 171801
• Molecular Formular: C12H11ClN2O5S
• Molecular Mass: 330.74414
• Monoisotopic Mass: 330.00772014
• SMILES: c1ccc(o1)CNc1cc(c(cc1S(=O)(=O)N)C(=O)O)Cl
• Canonical SMILES: OC(=O)c1cc(c(cc1Cl)NCc1ccco1)S(=O)(=O)N
• InChI: InChI=1S/C12H11ClN2O5S/c13-9-5-10(15-6-7-2-1-3-20-7)11(21(14,18)19)4-8(9)12(16)17/h1-5,15H,6H2,(H,16,17)(H2,14,18,19)
• InChIKey: UXOOVYKVEXGCSH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-chloro-4-[(furan-2-ylmethyl)amino]-5-sulfamoylbenzoic acid
• IUPAC Traditional name: 2-chloro-4-[(furan-2-ylmethyl)amino]-5-sulfamoylbenzoic acid
• Synonyms: 5-(Aminosulfonyl)-2-chloro-4-[(2-furanylmethyl)amino]benzoic Acid; 2-Chloro-4-(furfurylamino)-5-sulfamoylbenzoic Acid; H 20; Isofurosemide; Isolasix; Iso Furosemide

Database IDs

• CAS Number: 4818-59-1
• PubChem SID: 164227711
• PubChem CID: 58344442

CALCULATED PROPERTIES

• Acid pKa: 3.4240375
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.96618026
• LogD (pH = 7.4): -2.2993503
• Log P: 1.098402
• Molar Refractivity: 77.4742 cm^3
• Polarizability: 29.496666 Å^3
• Polar Surface Area: 122.63 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - I818500

A Furosemide (F865000) derivative which enhanced urinary excretion of active kallikrein.

REFERENCES

• Kirk, K., et al.: J. Biol. Chem., 267, 23475 (1992)
• Kirk, K., et al.: Biochem. J., 311, 761 (1992)
• Egee, S., et al.: J. Physiol., 542, 795 ( 2002),