(2R)-N-[(4R,5R)-3,11-dioxo-10-oxa-6-thia-2-azatricyclo[6.3.0.02,5]undec-1(8)-en-4-yl]-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetamide

• ChemBase ID: 166589
• Molecular Formular: C23H23N5O8S
• Molecular Mass: 529.52242
• Monoisotopic Mass: 529.12673372
• SMILES: [C@@H](NC(=O)N1CCN(C(=O)C1=O)CC)(c1ccc(cc1)O)C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC1=C2C(=O)OC1
• Canonical SMILES: CCN1CCN(C(=O)C1=O)C(=O)N[C@@H](C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC1=C2C(=O)OC1)c1ccc(cc1)O
• InChI: InChI=1S/C23H23N5O8S/c1-2-26-7-8-27(20(33)19(26)32)23(35)25-14(11-3-5-13(29)6-4-11)17(30)24-15-18(31)28-16-12(9-36-22(16)34)10-37-21(15)28/h3-6,14-15,21,29H,2,7-10H2,1H3,(H,24,30)(H,25,35)/t14-,15-,21-/m1/s1
• InChIKey: RFNBMKDSMYYHTH-VTJXTGGHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-N-[(4R,5R)-3,11-dioxo-10-oxa-6-thia-2-azatricyclo[6.3.0.0^2,^5]undec-1(8)-en-4-yl]-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetamide
• IUPAC Traditional name: (2R)-N-[(4R,5R)-3,11-dioxo-10-oxa-6-thia-2-azatricyclo[6.3.0.0^2,^5]undec-1(8)-en-4-yl]-2-(4-ethyl-2,3-dioxopiperazine-1-carbonylamino)-2-(4-hydroxyphenyl)acetamide
• Synonyms: [5aR-[5aα,6β(R*)]]-4-Ethyl-N-[1-(4-hydroxyphenyl)-2-oxo-2-[(1,4,5a,6-tetrahydro-1,7-dioxo-3H,7H-azeto[2,1-b]furo[3,4-d][1,3]thiazin-6-yl)amino]ethyl]-2,3-dioxo-1-piperazinecarboxamide; Des-(N-methyl-5-tetrazolethiolyl)furolactone Cefoperazone

Database IDs

• CAS Number: 73240-08-1
• PubChem SID: 162260722
• PubChem CID: 71315795

CALCULATED PROPERTIES

• Acid pKa: 9.470978
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -1.082709
• LogD (pH = 7.4): -1.0863103
• Log P: -1.0826629
• Molar Refractivity: 128.0102 cm^3
• Polarizability: 49.242718 Å^3
• Polar Surface Area: 165.66 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D294325

Cefoperazone impurity.

REFERENCES

• Sugiyama, I., et al.: J. Antibiot., 45,103 (1992)
• Gazdic, A., et al.: Med. Arch., 52, 207 (1992)
• Long, R., et al.: Can. Med. Assoc. J., 163, 425 (1992)