(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)(4,4,5,5,5-2H5)pent-2-enamido]-3-[(carbamoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 163893
• Molecular Formular: C17H19N5O6S2
• Molecular Mass: 453.49266
• Monoisotopic Mass: 453.07767535
• SMILES: [C@@H]12N(C(=C(CS1)COC(=O)N)C(=O)O)C(=O)[C@H]2NC(=O)/C(=C\CC)/c1csc(n1)N
• Canonical SMILES: CC/C=C(/c1csc(n1)N)\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)COC(=O)N
• InChI: InChI=1S/C17H19N5O6S2/c1-2-3-8(9-6-30-16(18)20-9)12(23)21-10-13(24)22-11(15(25)26)7(4-28-17(19)27)5-29-14(10)22/h3,6,10,14H,2,4-5H2,1H3,(H2,18,20)(H2,19,27)(H,21,23)(H,25,26)/b8-3-/t10-,14-/m1/s1
• InChIKey: HJJRIJDTIPFROI-NVKITGPLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)(4,4,5,5,5-^2H₅)pent-2-enamido]-3-[(carbamoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)(4,4,5,5,5-^2H₅)pent-2-enamido]-3-[(carbamoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: (6R,7R)-3-[[(Aminocarbonyl)oxy]methyl]-7-[[(2Z)-2-(2-amino-4-thiazolyl)-1-oxo-2-penten-1-yl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid-d5; Cefcamate-d5; Cefcapene Pivoxil Free Acid-d5; S 1006-d5; Cefcapene-d5

Database IDs

• PubChem SID: 162258028
• PubChem CID: 71314598

CALCULATED PROPERTIES

• Acid pKa: 3.1114602
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -2.0197608
• LogD (pH = 7.4): -3.3143232
• Log P: -0.9117881
• Molar Refractivity: 109.2433 cm^3
• Polarizability: 41.350983 Å^3
• Polar Surface Area: 177.94 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C242547

Labelled Cefcapene (C242545). Cefcapene is a metabolite of Cefcapene Pivoxil (C242550). Antibacterial, orally absorbed cephalosporin.

REFERENCES

• Neu, H.C., et al.: Antimicrob.Agents Chemother., 36, 1336 (1992)
• Ishikura, K., et al.: J. Antibiot., 47, 466 (1992)