(5R)-5-[(4-{[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]methoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione

• ChemBase ID: 6215
• Molecular Formular: C24H27NO5S
• Molecular Mass: 441.53988
• Monoisotopic Mass: 441.16099397
• SMILES: C1Cc2c(C)c(O)c(C)c(C)c2O[C@@]1(C)COc1ccc(cc1)C[C@H]1SC(=O)NC1=O
• Canonical SMILES: O=C1NC(=O)[C@H](S1)Cc1ccc(cc1)OC[C@@]1(C)CCc2c(O1)c(C)c(c(c2C)O)C
• InChI: InChI=1S/C24H27NO5S/c1-13-14(2)21-18(15(3)20(13)26)9-10-24(4,30-21)12-29-17-7-5-16(6-8-17)11-19-22(27)25-23(28)31-19/h5-8,19,26H,9-12H2,1-4H3,(H,25,27,28)/t19-,24-/m1/s1
• InChIKey: GXPHKUHSUJUWKP-NTKDMRAZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5R)-5-[(4-{[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]methoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione
• IUPAC Traditional name: rezulin
• Synonyms: (5R)-5-(4-{[(2R)-6-HYDROXY-2,5,7,8-TETRAMETHYL-3,4-DIHYDRO-2H-CHROMEN-2-YL]METHOXY}BENZYL)-1,3-THIAZOLIDINE-2,4-DIONE

Database IDs

• PubChem SID: 160969640; 99445078
• PubChem CID: 9824580

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.613558
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 5.463373
• LogD (pH = 7.4): 4.6721177
• Log P: 5.4952044
• Molar Refractivity: 120.9914 cm^3
• Polarizability: 46.61733 Å^3
• Polar Surface Area: 84.86 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 4.16
• LOG S: -5.56
• Solubility (Water): 1.21e-03 g/l

DETAILS

DrugBank - DB08607

Drug information: experimental