(6R,7S)-7-{4-[carbamoyl(carboxy)methylidene]-1,3-dithietane-2-amido}-7-methoxy-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 163921
• Molecular Formular: C17H17N7O8S4
• Molecular Mass: 575.61898
• Monoisotopic Mass: 575.00214454
• SMILES: C\1(=C(/C(=O)N)\C(=O)O)/SC(S1)C(=O)N[C@@]1(C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1n(nnn1)C)OC
• Canonical SMILES: CO[C@@]1(NC(=O)C2S/C(=C(\C(=O)O)/C(=O)N)/S2)C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1nnnn1C
• InChI: InChI=1S/C17H17N7O8S4/c1-23-16(20-21-22-23)34-4-5-3-33-15-17(32-2,14(31)24(15)7(5)11(29)30)19-9(26)13-35-12(36-13)6(8(18)25)10(27)28/h13,15H,3-4H2,1-2H3,(H2,18,25)(H,19,26)(H,27,28)(H,29,30)/b12-6-/t13?,15-,17+/m1/s1
• InChIKey: SRZNHPXWXCNNDU-IXOPCIAXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7S)-7-{4-[carbamoyl(carboxy)methylidene]-1,3-dithietane-2-amido}-7-methoxy-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: cefotetan
• Synonyms: (6R,7S)-7-[[[4-(2-Amino-1-carboxy-2-oxoethylidene)-1,3-dithietan-2-yl]carbonyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; Apacef; Cefotetan

Database IDs

• CAS Number: 69712-56-7
• PubChem SID: 162258056
• PubChem CID: 53025

CALCULATED PROPERTIES

• Acid pKa: 3.2314074
• H Acceptors: 11
• H Donor: 4
• LogD (pH = 5.5): -4.074055
• LogD (pH = 7.4): -6.970815
• Log P: -0.37600145
• Molar Refractivity: 153.5523 cm^3
• Polarizability: 50.305107 Å^3
• Polar Surface Area: 219.93 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Off-White Solid
• Melting Point: 173-178°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C242970

An antibiotic related to Cephalosporin, used in the treatment of bacterial infections.

REFERENCES

• Ahmed, A., et al.: Vet. Microbiol., 136, 397 (2009)
• Kim, M., et al.: J. Bacteriol. Virol., 39, 29 (2009)
• Fourches, D., et al.: Chem. Res. Toxicol., 23, 171 (2009)