5-cyclopropyl-2-(4-fluorophenyl)-6-[N-(2-hydroxyethyl)methanesulfonamido]-N-methyl-1-benzofuran-3-carboxamide

• ChemBase ID: 4889
• Molecular Formular: C22H23FN2O5S
• Molecular Mass: 446.4918232
• Monoisotopic Mass: 446.13117107
• SMILES: C1C(C1)c1c(cc2c(c1)c(c(c1ccc(cc1)F)o2)C(=O)NC)N(S(=O)(=O)C)CCO
• Canonical SMILES: OCCN(S(=O)(=O)C)c1cc2oc(c(c2cc1C1CC1)C(=O)NC)c1ccc(cc1)F
• InChI: InChI=1S/C22H23FN2O5S/c1-24-22(27)20-17-11-16(13-3-4-13)18(25(9-10-26)31(2,28)29)12-19(17)30-21(20)14-5-7-15(23)8-6-14/h5-8,11-13,26H,3-4,9-10H2,1-2H3,(H,24,27)
• InChIKey: WTDWVLJJJOTABN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-cyclopropyl-2-(4-fluorophenyl)-6-[N-(2-hydroxyethyl)methanesulfonamido]-N-methyl-1-benzofuran-3-carboxamide
• IUPAC Traditional name: nesbuvir
• Synonyms: 5-cyclopropyl-2-(4-fluorophenyl)-6-[(2-hydroxyethyl)(methylsulfonyl)amino]-N-methyl-1-benzofuran-3-carboxamide

Database IDs

• PubChem SID: 99443709; 160968321
• PubChem CID: 11561383

CALCULATED PROPERTIES

JChem

• Acid pKa: 15.337882
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.6046104
• LogD (pH = 7.4): 1.6046104
• Log P: 1.6046104
• Molar Refractivity: 114.3651 cm^3
• Polarizability: 46.171165 Å^3
• Polar Surface Area: 99.85 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.34
• LOG S: -3.85
• Solubility (Water): 6.31e-02 g/l

DETAILS

DrugBank - DB07238

Drug information: experimental