(6R,7R)-7-[(2R)-2-amino-2-(2H5)phenylacetamido]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 163868
• Molecular Formular: C15H14ClN3O4S
• Molecular Mass: 367.80736
• Monoisotopic Mass: 367.03935462
• SMILES: [C@H]1(C(=O)N2[C@@H]1SCC(=C2C(=O)O)Cl)NC(=O)[C@@H](c1ccccc1)N
• Canonical SMILES: N[C@H](c1ccccc1)C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)Cl
• InChI: InChI=1S/C15H14ClN3O4S/c16-8-6-24-14-10(13(21)19(14)11(8)15(22)23)18-12(20)9(17)7-4-2-1-3-5-7/h1-5,9-10,14H,6,17H2,(H,18,20)(H,22,23)/t9-,10-,14-/m1/s1
• InChIKey: QYIYFLOTGYLRGG-GPCCPHFNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2R)-2-amino-2-(^2H₅)phenylacetamido]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: (6R,7R)-7-[(2R)-2-amino-2-(^2H₅)phenylacetamido]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: (6R,7R)-7-[(2-Amino-2-(phenyl-d5)acetyl)amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; Ceclor-d5; Distaclor-d5; Keflor-d5; Raniclor-d5; Cefaclor-d5

Database IDs

• PubChem SID: 162258003
• PubChem CID: 46780201

CALCULATED PROPERTIES

• Acid pKa: 3.0266292
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.3069453
• LogD (pH = 7.4): -2.5625703
• Log P: -2.3063354
• Molar Refractivity: 89.5618 cm^3
• Polarizability: 34.716232 Å^3
• Polar Surface Area: 112.73 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C235252

Second-generation labelled cephalosporin antibiotic. Antibacterial.

REFERENCES

• Gray, B.M., et al.: Antimicrob. Agents Chemother., 13, 988 (1978)
• Lorenz, L.J., et al.: Anal. Profiles Drug Subs., 9, 107 (1978)
• Hori, R., et al.: J. Pharm. Pharmacol., 40, 646 (1978)