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

• ChemBase ID: 163897
• Molecular Formular: C23H29N5O8S2
• Molecular Mass: 567.63506
• Monoisotopic Mass: 567.14575491
• SMILES: [C@@H]12N(C(C(=CS1)COC(=O)N)C(=O)OCOC(=O)C(C)(C)C)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]1SC=C(C2C(=O)OCOC(=O)C(C)(C)C)COC(=O)N
• InChI: InChI=1S/C23H29N5O8S2/c1-5-6-12(13-9-38-21(24)26-13)16(29)27-14-17(30)28-15(11(7-34-22(25)33)8-37-18(14)28)19(31)35-10-36-20(32)23(2,3)4/h6,8-9,14-15,18H,5,7,10H2,1-4H3,(H2,24,26)(H2,25,33)(H,27,29)/b12-6-/t14-,15?,18-/m1/s1
• InChIKey: JQAWVGMIOMFLAY-ANFSUHFESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)pent-2-enamido]-3-[(carbamoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carbonyloxy]methyl 2,2-dimethylpropanoate
• IUPAC Traditional name: [(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)pent-2-enamido]-3-[(carbamoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carbonyloxy]methyl 2,2-dimethylpropanoate
• Synonyms: (6R,7R)-3-[[(Aminocarbonyl)oxy]methyl]-7-[[(2Z)-2-(2-amino-4-thiazolyl)-1-oxo-2-pentenyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic Acid (2,2-Dimethyl-1-oxopropoxy)methyl Ester; Δ2-Cefcapene Pivoxil

Database IDs

• PubChem SID: 162258032
• PubChem CID: 71314599

CALCULATED PROPERTIES

• Acid pKa: 11.600655
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 1.7952319
• LogD (pH = 7.4): 1.8052443
• Log P: 1.8053981
• Molar Refractivity: 136.6845 cm^3
• Polarizability: 53.412083 Å^3
• Polar Surface Area: 193.24 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C242560

Cefcapene Pivoxil (C242550) derivative. Δ2-Cephalosporins are potentially related compounds in cephalosporin antibacterial compounds.

REFERENCES

• Chavette, R.R., J. Med. Chem., 9, 741 (1966)
• Miyouchi, M., et al.: J. Chem. Pharm. Bull., 38, 1906 (1966)
• Sugioka, T., et al.: Chem. Pharm. Bull., 38, 1998 (1966)