2-{4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy}acetic acid

• ChemBase ID: 153300
• Molecular Formular: C12H9NO5S
• Molecular Mass: 279.26856
• Monoisotopic Mass: 279.02014339
• SMILES: c1cc(ccc1/C=C\1/C(=O)NC(=O)S1)OCC(=O)O
• Canonical SMILES: OC(=O)COc1ccc(cc1)/C=C/1\SC(=O)NC1=O
• InChI: InChI=1S/C12H9NO5S/c14-10(15)6-18-8-3-1-7(2-4-8)5-9-11(16)13-12(17)19-9/h1-5H,6H2,(H,14,15)(H,13,16,17)
• InChIKey: WXMCOLGPDOYHNK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy}acetic acid
• IUPAC Traditional name: 4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxyacetic acid
• Synonyms: 2-[4-[(2,4-Dioxo-5-thiazolidinylidene)methyl]phenoxy]-acetic acid; GPR35 Agonist, Compound 10

Database IDs

• CAS Number: 123021-85-2
• PubChem SID: 162247439
• PubChem CID: 2295463

CALCULATED PROPERTIES

• Acid pKa: 3.3918242
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.9268017
• LogD (pH = 7.4): -2.3518353
• Log P: 1.170271
• Molar Refractivity: 68.7688 cm^3
• Polarizability: 26.170153 Å^3
• Polar Surface Area: 92.7 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥5 mg/mL at ~60 °C
• Apperance: white to tan powder

Safety Information

• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C12H9NO5S

DETAILS

Sigma Aldrich - SML0174

Biochem/physiol Actions
GPR35 agonist Compound 10 is a GPR35 agonist the binds with higher affinity than other known agonists, such as kynurenic acid and zaprinast. Compound 10 was more potent than zaniprast (pEC50 = 5.3 vs 4.18) for recombinantly expressed human GPR35, and unlike zaprinast, is equipotent for human and rat GPR35