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

• ChemBase ID: 166250
• Molecular Formular: C16H18N6O6S3
• Molecular Mass: 486.54572
• Monoisotopic Mass: 486.04499533
• SMILES: [C@H]1(C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSCC(=O)N)NC(=O)/C(=N\OC)/c1nc(sc1)N
• Canonical SMILES: CO/N=C(\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSCC(=O)N)/c1csc(n1)N
• InChI: InChI=1S/C16H18N6O6S3/c1-28-21-9(7-4-31-16(18)19-7)12(24)20-10-13(25)22-11(15(26)27)6(3-30-14(10)22)2-29-5-8(17)23/h4,10,14H,2-3,5H2,1H3,(H2,17,23)(H2,18,19)(H,20,24)(H,26,27)/b21-9-/t10-,14-/m1/s1
• InChIKey: PLZQZSMSRGAYQG-ZSDSSEDPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-{[(carbamoylmethyl)sulfanyl]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-(methoxyimino)acetamido]-3-{[(carbamoylmethyl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: (6R,7R)-3-[[(2-Amino-2-oxoethyl)thio]methyl]-7-[[(2Z)-2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; Desfuroyl Ceftiofur S-Acetamide

Database IDs

• CAS Number: 120882-25-9
• PubChem SID: 162260383
• PubChem CID: 71315646

CALCULATED PROPERTIES

• Acid pKa: 3.2757761
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -3.335297
• LogD (pH = 7.4): -4.5902066
• Log P: -2.2914653
• Molar Refractivity: 114.6908 cm^3
• Polarizability: 43.543983 Å^3
• Polar Surface Area: 190.3 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Low Melting Solid

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D289900

A 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)