5,5-dimethyl-2-[(2-phenoxyacetamido)methyl]-1,3-thiazolidine-4-carboxylic acid

• ChemBase ID: 176395
• Molecular Formular: C15H20N2O4S
• Molecular Mass: 324.3953
• Monoisotopic Mass: 324.11437813
• SMILES: C1(SC(NC1C(=O)O)CNC(=O)COc1ccccc1)(C)C
• Canonical SMILES: O=C(COc1ccccc1)NCC1NC(C(S1)(C)C)C(=O)O
• InChI: InChI=1S/C15H20N2O4S/c1-15(2)13(14(19)20)17-12(22-15)8-16-11(18)9-21-10-6-4-3-5-7-10/h3-7,12-13,17H,8-9H2,1-2H3,(H,16,18)(H,19,20)
• InChIKey: NABJOXIJXQOSPN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,5-dimethyl-2-[(2-phenoxyacetamido)methyl]-1,3-thiazolidine-4-carboxylic acid
• IUPAC Traditional name: 5,5-dimethyl-2-[(2-phenoxyacetamido)methyl]-1,3-thiazolidine-4-carboxylic acid
• Synonyms: 5,5-Dimethyl-2-[[(2-phenoxyacetyl)amino]methyl]-4-thiazolidinecarboxylic Acid; Penilloic Acid V; Phenoxymethylpenilloic Acid (Mixture of Diastereomers)

Database IDs

• CAS Number: 4847-29-4
• PubChem SID: 164232305
• PubChem CID: 4188041

CALCULATED PROPERTIES

• Acid pKa: 2.8038218
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.1468276
• LogD (pH = 7.4): -1.6614703
• Log P: -1.1378448
• Molar Refractivity: 83.0159 cm^3
• Polarizability: 33.20496 Å^3
• Polar Surface Area: 87.66 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 146-148°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - P298250

A degradation product of Penicillins. A reversible competitive inhibitor of Penicillinase, β-Lactamase 1.

REFERENCES

• Kiener, P.A., et al.: Biochem. J., 169, 197 (1978)
• Hilder, E., et al.: Electrophoresis, 23, 414 (1978)
• Pajchel, G., et al.: J. Pharm. Biomed. Anal., 32, 59 (1978)