2-[(5E)-5-[(2E)-2-methyl-3-phenylprop-2-en-1-ylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid

• ChemBase ID: 168023
• Molecular Formular: C15H13NO3S2
• Molecular Mass: 319.39862
• Monoisotopic Mass: 319.03368528
• SMILES: c1cccc(c1)/C=C(/C=C/1\C(=O)N(C(=S)S1)CC(=O)O)\C
• Canonical SMILES: C/C(=C\c1ccccc1)/C=C\1/SC(=S)N(C1=O)CC(=O)O
• InChI: InChI=1S/C15H13NO3S2/c1-10(7-11-5-3-2-4-6-11)8-12-14(19)16(9-13(17)18)15(20)21-12/h2-8H,9H2,1H3,(H,17,18)/b10-7+,12-8+
• InChIKey: CHNUOJQWGUIOLD-SMTGYRLFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(5E)-5-[(2E)-2-methyl-3-phenylprop-2-en-1-ylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid
• IUPAC Traditional name: [(5E)-5-[(2E)-2-methyl-3-phenylprop-2-en-1-ylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid
• Synonyms: (5Z)-5-[(2E)-2-Methyl-3-phenyl-2-propen-1-ylidene]-4-oxo-2-thioxo-3-thiazolidineacetic Acid; Eabeth; Kinedak; ONO 2235; Sorbistat; Epalrestat

Database IDs

• CAS Number: 82159-09-9
• PubChem SID: 162262155
• PubChem CID: 1584822

CALCULATED PROPERTIES

• Acid pKa: 3.6996162
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.4128873
• LogD (pH = 7.4): -0.093563095
• Log P: 3.212065
• Molar Refractivity: 89.7938 cm^3
• Polarizability: 34.027493 Å^3
• Polar Surface Area: 57.61 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; DMSO
• Apperance: Red Solid
• Melting Point: 218-221°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - E565300

An aldose reductase inhibitor. It is used in treatment of diabetic neuropathy.

REFERENCES

• Terashima, H., et al.: J. Pharmacol. Exp. Ther., 229, 226 (1983)
• Kikkawa, R., et al.: Diabetologia, 24, 290 (1983)
• Kojima, K., et al.: Jpn. J. Ophthalmol., 29, 99 (1983)