(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-3-ene-2-carboxylic acid

• ChemBase ID: 163920
• 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]1SC=C(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]1SC=C(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/h3,7,13,15H,4H2,1-2H3,(H2,18,25)(H,19,26)(H,27,28)(H,29,30)/b12-6-/t7?,13?,15-,17+/m1/s1
• InChIKey: DBSPFHNCVUTGLP-APKJNDLBSA-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-3-ene-2-carboxylic acid
• IUPAC Traditional name: (6R,7S)-7-{4-[carbamoyl(carboxy)methylidene]-1,3-dithietane-2-amido}-7-methoxy-3-{[(1-methyl-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid
• Synonyms: Δ2-Cefotetan

Database IDs

• CAS Number: 1332499-75-8
• PubChem SID: 162258055
• PubChem CID: 56847127

CALCULATED PROPERTIES

• Acid pKa: 2.9741657
• H Acceptors: 11
• H Donor: 4
• LogD (pH = 5.5): -4.459365
• LogD (pH = 7.4): -7.1222024
• Log P: -0.4682159
• Molar Refractivity: 152.2687 cm^3
• Polarizability: 50.310135 Å^3
• Polar Surface Area: 219.93 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Light Tan Solid
• Melting Point: 178-180°C

Safety Information

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

DETAILS

Toronto Research Chemicals - C242965

The Δ2-isomer of Cefotean (C242970). It is useful as intermediate in the preparation of cephalesorin compounds.

REFERENCES

• Sugioka, T., et al.: Chem. Pharm. Bull., 38, 1998 (1990)