(4S)-2-({[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]formamido}methyl)-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid

• ChemBase ID: 169022
• Molecular Formular: C18H19ClFN3O4S
• Molecular Mass: 427.8775632
• Monoisotopic Mass: 427.076883
• SMILES: C1(SC(N[C@H]1C(=O)O)CNC(=O)c1c(noc1C)c1c(cccc1Cl)F)(C)C
• Canonical SMILES: OC(=O)[C@@H]1NC(SC1(C)C)CNC(=O)c1c(C)onc1c1c(F)cccc1Cl
• InChI: InChI=1S/C18H19ClFN3O4S/c1-8-12(14(23-27-8)13-9(19)5-4-6-10(13)20)16(24)21-7-11-22-15(17(25)26)18(2,3)28-11/h4-6,11,15,22H,7H2,1-3H3,(H,21,24)(H,25,26)/t11?,15-/m0/s1
• InChIKey: GBFSDMWQIFGGKS-MHTVFEQDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-2-({[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]formamido}methyl)-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
• IUPAC Traditional name: (4S)-2-({[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]formamido}methyl)-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
• Synonyms: 2-[[[[3-(2-Chloro-6-fluorophenyl)-5-methyl-4-isoxazolyl]carbonyl]amino]methyl]-5,5-dimethyl-4-thiazolidinecarboxylic Acid; Flucloxacillin Penilloic Acid(Mixture of Diastereomers)

Database IDs

• PubChem SID: 162263154
• PubChem CID: 71316777

CALCULATED PROPERTIES

• Acid pKa: 3.1545298
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 0.6300282
• LogD (pH = 7.4): 0.05727876
• Log P: 0.6390213
• Molar Refractivity: 104.1014 cm^3
• Polarizability: 40.82314 Å^3
• Polar Surface Area: 104.46 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F419180

A degradation product/impurity of Flucloxacillin (F419200).

REFERENCES

• Aboul K.A., et al.: Anal. Lett., 17, 1667 (1984)