methyl 3-{[2-methoxy-4-(phenylamino)phenyl]sulfamoyl}thiophene-2-carboxylate

• ChemBase ID: 154344
• Molecular Formular: C19H18N2O5S2
• Molecular Mass: 418.48662
• Monoisotopic Mass: 418.06571369
• SMILES: COc1cc(ccc1NS(=O)(=O)c1ccsc1C(=O)OC)Nc1ccccc1
• Canonical SMILES: COC(=O)c1sccc1S(=O)(=O)Nc1ccc(cc1OC)Nc1ccccc1
• InChI: InChI=1S/C19H18N2O5S2/c1-25-16-12-14(20-13-6-4-3-5-7-13)8-9-15(16)21-28(23,24)17-10-11-27-18(17)19(22)26-2/h3-12,20-21H,1-2H3
• InChIKey: NDFKBGWLUHKMFY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 3-{[2-methoxy-4-(phenylamino)phenyl]sulfamoyl}thiophene-2-carboxylate
• IUPAC Traditional name: methyl 3-{[2-methoxy-4-(phenylamino)phenyl]sulfamoyl}thiophene-2-carboxylate
• Synonyms: 3-(((2-Methoxy-4-(phenylamino)phenyl)amino]sulfonyl)-2-thiophenecarboxylic acid methyl ester; GSK0660

Database IDs

• CAS Number: 1014691-61-2
• MDL Number: MFCD12828770
• PubChem SID: 162248483
• PubChem CID: 46233311

CALCULATED PROPERTIES

• Acid pKa: 6.270565
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 3.5997849
• LogD (pH = 7.4): 2.9032
• Log P: 3.659524
• Molar Refractivity: 106.7548 cm^3
• Polarizability: 41.62059 Å^3
• Polar Surface Area: 93.73 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: tan solid

Safety Information

• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H18N2O5S2

DETAILS

Sigma Aldrich - G5797

Biochem/physiol Actions
GSK0660 is a potent PPARβ/δ antagonist with a pIC50 of 6.8 (160 nM). GSK0660 is nearly inactive on PPARα and PPARγ with IC50s greater than 10 μM.