(2R)-2-[4-(but-2-yn-1-yloxy)benzenesulfonamido]-3-(5-methyl-1H-indol-3-yl)propanoic acid

• ChemBase ID: 4884
• Molecular Formular: C22H22N2O5S
• Molecular Mass: 426.48548
• Monoisotopic Mass: 426.12494281
• SMILES: c1c2c(cc(c1)C)c(c[nH]2)C[C@H](C(=O)O)NS(=O)(=O)c1ccc(cc1)OCC#CC
• Canonical SMILES: CC#CCOc1ccc(cc1)S(=O)(=O)N[C@@H](C(=O)O)Cc1c[nH]c2c1cc(C)cc2
• InChI: InChI=1S/C22H22N2O5S/c1-3-4-11-29-17-6-8-18(9-7-17)30(27,28)24-21(22(25)26)13-16-14-23-20-10-5-15(2)12-19(16)20/h5-10,12,14,21,23-24H,11,13H2,1-2H3,(H,25,26)/t21-/m1/s1
• InChIKey: SFVPXERGVLDWIS-OAQYLSRUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-[4-(but-2-yn-1-yloxy)benzenesulfonamido]-3-(5-methyl-1H-indol-3-yl)propanoic acid
• IUPAC Traditional name: (2R)-2-[4-(but-2-yn-1-yloxy)benzenesulfonamido]-3-(5-methyl-1H-indol-3-yl)propanoic acid
• Synonyms: N-{[4-(but-2-yn-1-yloxy)phenyl]sulfonyl}-5-methyl-D-tryptophan

Database IDs

• PubChem SID: 160968316; 99443704
• PubChem CID: 42627769

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.2690468
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.8128592
• LogD (pH = 7.4): 0.5922105
• Log P: 4.0250516
• Molar Refractivity: 113.982 cm^3
• Polarizability: 45.139484 Å^3
• Polar Surface Area: 108.49 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.77
• LOG S: -5.27
• Solubility (Water): 2.29e-03 g/l

DETAILS

DrugBank - DB07233

Drug information: experimental