(2S,5R,6R)-6-[3-(2-chloro-6-fluorophenyl)-5-(hydroxymethyl)-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

• ChemBase ID: 170842
• Molecular Formular: C19H17ClFN3O6S
• Molecular Mass: 469.8711832
• Monoisotopic Mass: 469.05106218
• SMILES: c1cc(c(c(c1)F)c1noc(c1C(=O)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C)CO)Cl
• Canonical SMILES: OCc1onc(c1C(=O)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C)c1c(F)cccc1Cl
• InChI: InChI=1S/C19H17ClFN3O6S/c1-19(2)14(18(28)29)24-16(27)13(17(24)31-19)22-15(26)11-9(6-25)30-23-12(11)10-7(20)4-3-5-8(10)21/h3-5,13-14,17,25H,6H2,1-2H3,(H,22,26)(H,28,29)/t13-,14+,17-/m1/s1
• InChIKey: ZUBWLMQDPXVIGD-JKIFEVAISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,5R,6R)-6-[3-(2-chloro-6-fluorophenyl)-5-(hydroxymethyl)-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• IUPAC Traditional name: (2S,5R,6R)-6-[3-(2-chloro-6-fluorophenyl)-5-(hydroxymethyl)-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• Synonyms: (2S,5R,6R)-6-[[[3-(2-Chloro-6-fluorophenyl)-5-(hydroxymethyl)-4-isoxazolyl]carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid; 5-Hydroxymethyl FlucloxacillinDISCONTINUED

Database IDs

• CAS Number: 75524-31-1
• PubChem SID: 164226752
• PubChem CID: 64708

CALCULATED PROPERTIES

• Acid pKa: 3.7055068
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -0.39595583
• LogD (pH = 7.4): -1.9057314
• Log P: 1.3975316
• Molar Refractivity: 108.3972 cm^3
• Polarizability: 42.47276 Å^3
• Polar Surface Area: 132.97 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H947840

A metabolite of Flucloxacillin.

REFERENCES

• Thijssen, H., et al.: J. Antibiot., 32, 1033 (1979)
• Ayres, R., et al.: J. Immunol. Methods, 141, 117 (1979)
• Bensoussan, C., et al.: Biochem. Pharmacol., 49, 591 (1979)
• Kostrubsky, V., et al.: Drug Metab. Dispos., 27, 887 (1979)