1-{[(6R,7R)-7-[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-5H,6H,7H-cyclopenta[b]pyridin-1-ium

• ChemBase ID: 163926
• Molecular Formular: C22H22N6O5S2
• Molecular Mass: 514.57728
• Monoisotopic Mass: 514.10930983
• SMILES: [C@H]1(C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])C[n+]1cccc2c1CCC2)NC(=O)/C(=N/OC)/c1csc(n1)N
• Canonical SMILES: CO/N=C(/C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])C[n+]1cccc2c1CCC2)\c1csc(n1)N
• InChI: InChI=1S/C22H22N6O5S2/c1-33-26-15(13-10-35-22(23)24-13)18(29)25-16-19(30)28-17(21(31)32)12(9-34-20(16)28)8-27-7-3-5-11-4-2-6-14(11)27/h3,5,7,10,16,20H,2,4,6,8-9H2,1H3,(H3-,23,24,25,29,31,32)/b26-15+/t16-,20-/m1/s1
• InChIKey: DKOQGJHPHLTOJR-PUIFZAHNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{[(6R,7R)-7-[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-5H,6H,7H-cyclopenta[b]pyridin-1-ium
• IUPAC Traditional name: 1-{[(6R,7R)-7-[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-5H,6H,7H-cyclopenta[b]pyridin-1-ium
• Synonyms: 1-[[(6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-6,7-dihydro-5H-cyclopenta[b]pyrindinium Inner Salt; Broact; Cefrom; Keitin; Cefpirome Sulfate

Database IDs

• CAS Number: 98753-19-6
• PubChem SID: 162258061
• PubChem CID: 6917674

CALCULATED PROPERTIES

• Acid pKa: 3.0890388
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -3.6693666
• LogD (pH = 7.4): -3.654118
• Log P: -3.9704733
• Molar Refractivity: 141.296 cm^3
• Polarizability: 48.871773 Å^3
• Polar Surface Area: 153.92 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Crystalline Powder
• Melting Point: 198-202°C (dec)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C243500

Fourth generation cephalosporin antibiotic.

REFERENCES

• Kavi, J., et al.: J. Antimicrob. Chemother., 22, 911 (1988)
• Horstmann, G., et al.: Arzneim.-Forsch., 40, 1250 (1988)