(6R,7S)-7-[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetamido]-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: 163917
• Molecular Formular: C25H27N9O8S2
• Molecular Mass: 645.66738
• Monoisotopic Mass: 645.14240087
• SMILES: [C@@H]1(C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1nnnn1C)NC(=O)[C@H](NC(=O)N1C(=O)C(=O)N(CC1)CC)c1ccc(cc1)O
• Canonical SMILES: CCN1CCN(C(=O)C1=O)C(=O)N[C@H](c1ccc(cc1)O)C(=O)N[C@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1nnnn1C
• InChI: InChI=1S/C25H27N9O8S2/c1-3-32-8-9-33(21(39)20(32)38)24(42)27-15(12-4-6-14(35)7-5-12)18(36)26-16-19(37)34-17(23(40)41)13(10-43-22(16)34)11-44-25-28-29-30-31(25)2/h4-7,15-16,22,35H,3,8-11H2,1-2H3,(H,26,36)(H,27,42)(H,40,41)/t15-,16+,22-/m1/s1
• InChIKey: GCFBRXLSHGKWDP-ZMPRRUGASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7S)-7-[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetamido]-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: (6R,7S)-7-[(2R)-2-(4-ethyl-2,3-dioxopiperazine-1-carbonylamino)-2-(4-hydroxyphenyl)acetamido]-3-{[(1-methyl-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: (6R,7S)-7-[[(2R)-2-[[(4-Ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; (6R,7S)-Cefoperazone

Database IDs

• CAS Number: 1315481-36-7
• PubChem SID: 162258052
• PubChem CID: 7048630

CALCULATED PROPERTIES

• Acid pKa: 3.3837204
• H Acceptors: 11
• H Donor: 4
• LogD (pH = 5.5): -3.0036721
• LogD (pH = 7.4): -4.3111243
• Log P: -0.9004894
• Molar Refractivity: 169.0571 cm^3
• Polarizability: 59.325363 Å^3
• Polar Surface Area: 220.26 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C242890

(6R,7S)-Cefoperazone is the enantiomer of Cefoperazone (C242900) as an impurity.

REFERENCES

• Fabre, H., et al.: J. Pharm. Sci., 73, 611 (1984)
• Strasters, J., et al.: Anal. Chem., 63, 2503 (1984)
• Chen, Z., et al.: World Notes Antibiot., 25, 249 (1984)