(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(2H3)methoxyimino]acetamido]-3-({[(2R)-2-amino-2-carboxyethyl]disulfanyl}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 166268
• Molecular Formular: C17H20N6O7S4
• Molecular Mass: 548.6367
• Monoisotopic Mass: 548.02763101
• SMILES: [C@H]1(C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSSC[C@H](N)C(=O)O)NC(=O)/C(=N\OC)/c1nc(sc1)N
• Canonical SMILES: CO/N=C(/c1csc(n1)N)\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSSC[C@@H](C(=O)O)N
• InChI: InChI=1S/C17H20N6O7S4/c1-30-22-9(8-5-32-17(19)20-8)12(24)21-10-13(25)23-11(16(28)29)6(2-31-14(10)23)3-33-34-4-7(18)15(26)27/h5,7,10,14H,2-4,18H2,1H3,(H2,19,20)(H,21,24)(H,26,27)(H,28,29)/b22-9-/t7-,10+,14+/m0/s1
• InChIKey: JOKBPDNPVWSNNL-YOFCFWCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(^2H₃)methoxyimino]acetamido]-3-({[(2R)-2-amino-2-carboxyethyl]disulfanyl}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(^2H₃)methoxyimino]acetamido]-3-({[(2R)-2-amino-2-carboxyethyl]disulfanyl}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: (6R,7R)-3-[[[(2R)-2-Amino-2-carboxyethyl]dithio]methyl]-7-[[(2Z)-2-(2-amino-4-thiazolyl)-2-(methoxyimino-d3)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; Desfuroylceftiofur Cysteine Disulfide-d3; DFC-CYS-d3; Desfuroyl Ceftiofur Cysteine Disulfide-d3

Database IDs

• PubChem SID: 162260401
• PubChem CID: 71315661

CALCULATED PROPERTIES

• Acid pKa: 1.6428663
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -5.0376835
• LogD (pH = 7.4): -6.358942
• Log P: -3.9965653
• Molar Refractivity: 128.6772 cm^3
• Polarizability: 49.340904 Å^3
• Polar Surface Area: 210.53 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dil. HCl
• Apperance: Pale Yellow Solid
• Melting Point: >203°C (dec.)

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D289907

A labelled Desfuroyl Ceftiofur-related metabolite that have the potential to be microbiologic active in swine muscle, kidney, liver and fat.

REFERENCES

• Gilbertson, T., et al.: J. Agric. Food Chem., 43, 229 (1995)
• Olson, S., et al.: Vet. Pharmacol. Therap., 21, 112 (1995)
• Hornish, R., et al.: Curr. Top Med. Chem., 2, 717 (1995)