(6R,7R)-7-[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetamido]-3-[(4-methyl-5-sulfanylidene-4,5-dihydro-1H-1,2,3,4-tetrazol-1-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 166686
• Molecular Formular: C25H27N9O8S2
• Molecular Mass: 645.66738
• Monoisotopic Mass: 645.14240087
• SMILES: [C@@H](NC(=O)N1CCN(C(=O)C1=O)CC)(c1ccc(cc1)O)C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)Cn1c(=S)n(nn1)C
• 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)Cn1nnn(c1=S)C
• InChI: InChI=1S/C25H27N9O8S2/c1-3-31-8-9-32(21(39)20(31)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(11-44-22(16)34)10-33-25(43)30(2)28-29-33/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: LGKWYRNERXMLTN-XCGNWRKASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetamido]-3-[(4-methyl-5-sulfanylidene-4,5-dihydro-1H-1,2,3,4-tetrazol-1-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: (6R,7R)-7-[(2R)-2-(4-ethyl-2,3-dioxopiperazine-1-carbonylamino)-2-(4-hydroxyphenyl)acetamido]-3-[(4-methyl-5-sulfanylidene-1,2,3,4-tetrazol-1-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: (6R,7R)-3-[(4,5-Dihydro-4-methyl-5-thioxo-1H-tetrazol-1-yl)methyl]-7-[[(2R)-2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; 5-Desthiolyl-5-thioxo Cefoperazone Discontinued

Database IDs

• CAS Number: 711598-76-4
• PubChem SID: 162260819
• PubChem CID: 71315826

CALCULATED PROPERTIES

• Acid pKa: 3.7110026
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -1.4173098
• LogD (pH = 7.4): -2.9337358
• Log P: 0.37091264
• Molar Refractivity: 161.9964 cm^3
• Polarizability: 60.1373 Å^3
• Polar Surface Area: 207.86 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D297500

Cefoperazone impurity.