(2R,4S)-2-[(S)-carboxy({[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: 169023
• Molecular Formular: C19H19ClFN3O6S
• Molecular Mass: 471.8870632
• Monoisotopic Mass: 471.06671224
• SMILES: C1(S[C@@H](N[C@H]1C(=O)O)[C@@H](NC(=O)c1c(noc1C)c1c(cccc1Cl)F)C(=O)O)(C)C
• Canonical SMILES: OC(=O)[C@@H]([C@@H]1N[C@H](C(S1)(C)C)C(=O)O)NC(=O)c1c(C)onc1c1c(F)cccc1Cl
• InChI: InChI=1S/C19H19ClFN3O6S/c1-7-10(12(24-30-7)11-8(20)5-4-6-9(11)21)15(25)22-13(17(26)27)16-23-14(18(28)29)19(2,3)31-16/h4-6,13-14,16,23H,1-3H3,(H,22,25)(H,26,27)(H,28,29)/t13-,14+,16-/m1/s1
• InChIKey: OYRPOONYKNQRKD-IJEWVQPXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4S)-2-[(S)-carboxy({[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: (2R,4S)-2-[(S)-carboxy({[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]formamido})methyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
• Synonyms: (αR,2R,4S)-4-Carboxy-α-[[[3-(2-chloro-6-fluorophenyl)-5-methyl-4-isoxazolyl]carbonyl]amino]-5,5-dimethyl-2-thiazolidineacetic Acid; [2R-[2α(R*),4β]]-4-carboxy-α-[[[3-(2-Chloro-6-fluorophenyl)-5-methyl-4-isoxazolyl]carbonyl]amino]-5,5-dimethyl-2-thiazolidineacetic Acid; (5R)-Flucloxacillin Penilloic Acid

Database IDs

• CAS Number: 42947-70-6
• PubChem SID: 162263155
• PubChem CID: 71316778

CALCULATED PROPERTIES

• Acid pKa: 2.9939663
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -1.0387609
• LogD (pH = 7.4): -3.4751234
• Log P: 0.22989024
• Molar Refractivity: 109.9313 cm^3
• Polarizability: 43.29958 Å^3
• Polar Surface Area: 141.76 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F419190

(5R)-Flucloxacillin Penilloic Acid is a metabolite and impurity of Flucloxacillin (F419200).

REFERENCES

• Keun, H.C. et al.: Anal. Chem., 80, 1073 (2008)
• Everett, J.R. et al.: J. Pharmac. Biomed. Anal., 7, 397 (2008)