3-[(5S)-1-benzyl-4-hydroxy-2-oxo-5-(propan-2-yl)-2,5-dihydro-1H-pyrrol-3-yl]-1$l^{6},2-benzothiazole-1,1-dione

• ChemBase ID: 5063
• Molecular Formular: C21H20N2O4S
• Molecular Mass: 396.4595
• Monoisotopic Mass: 396.11437813
• SMILES: O=S1(=O)c2ccccc2C(=N1)C1=C([C@@H](N(C1=O)Cc1ccccc1)C(C)C)O
• Canonical SMILES: CC([C@@H]1N(Cc2ccccc2)C(=O)C(=C1O)C1=NS(=O)(=O)c2c1cccc2)C
• InChI: InChI=1S/C21H20N2O4S/c1-13(2)19-20(24)17(21(25)23(19)12-14-8-4-3-5-9-14)18-15-10-6-7-11-16(15)28(26,27)22-18/h3-11,13,19,24H,12H2,1-2H3/t19-/m0/s1
• InChIKey: XKOAFAIRGVAHRA-IBGZPJMESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(5S)-1-benzyl-4-hydroxy-2-oxo-5-(propan-2-yl)-2,5-dihydro-1H-pyrrol-3-yl]-1$l^{6},2-benzothiazole-1,1-dione
• IUPAC Traditional name: 3-[(5S)-1-benzyl-4-hydroxy-5-isopropyl-2-oxo-5H-pyrrol-3-yl]-1$l^{6},2-benzothiazole-1,1-dione
• Synonyms: (5S)-1-benzyl-3-(1,1-dioxido-1,2-benzisothiazol-3-yl)-4-hydroxy-5-(1-methylethyl)-1,5-dihydro-2H-pyrrol-2-one

Database IDs

• PubChem SID: 160968494; 99443885
• PubChem CID: 46937070

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.078705
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.5806415
• LogD (pH = 7.4): 1.3434359
• Log P: 2.682462
• Molar Refractivity: 107.0196 cm^3
• Polarizability: 41.47933 Å^3
• Polar Surface Area: 87.04 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.85
• LOG S: -4.14
• Solubility (Water): 2.89e-02 g/l

DETAILS

DrugBank - DB07414

Drug information: experimental