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

• ChemBase ID: 70016
• Molecular Formular: C15H13NO3S2
• Molecular Mass: 319.39862
• Monoisotopic Mass: 319.03368528
• SMILES: C(=O)(CN1C(=S)S/C(=C\C(=C\c2ccccc2)\C)/C1=O)O
• 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-NFZZJPOKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(5Z)-5-[(2E)-2-methyl-3-phenylprop-2-en-1-ylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid
• IUPAC Traditional name: kinedak; 2-[(5Z)-5-[(2E)-2-methyl-3-phenylprop-2-en-1-ylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid
• Synonyms: Epalrestat; 2-((Z)-5-((E)-2-methyl-3-phenylallylidene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid; Ropestatin; Kinedak; Epalrestat

Database IDs

• CAS Number: 82159-09-9
• MDL Number: MFCD00865484
• PubChem SID: 162035741
• PubChem CID: 1549120

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

Safety Information

• Storage Condition: -20°C
• Storage Warning: IRRITANT
• TSCA Listed: false

Pharmacology Properties

• Mechanism of Action: Aldose reductase inhibitor

Product Information

• Purity: 95+%
• Salt Data: Free Base
• Description: Isomers
• Application(s): Used against diabetic neuropathy

DETAILS

Selleck Chemicals - S2035

Research Area: Metabolic Disease
Biological Activity:

InterBioScreen - BB_SC-9906

Isomers

REFERENCES

• Eur. Pat., 1982, 47 109; CA, 97, 23781x, (synth)
• Asano, T. et al., CA, 1984, 100, 132471x
• Terashima, H. et al., J. Pharmacol. Exp. Ther., 1984, 229, 226, (pharmacol)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 279