(7R)-7-[(2R)-2-amino-2-phenylacetamido]-3-methyl-5,8-dioxo-5λ4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 163978
• Molecular Formular: C16H17N3O5S
• Molecular Mass: 363.38828
• Monoisotopic Mass: 363.08889166
• SMILES: c1cccc(c1)[C@H](C(=O)N[C@@H]1C(=O)N2C1S(=O)CC(=C2C(=O)O)C)N
• Canonical SMILES: N[C@H](c1ccccc1)C(=O)N[C@@H]1C(=O)N2C1S(=O)CC(=C2C(=O)O)C
• InChI: InChI=1S/C16H17N3O5S/c1-8-7-25(24)15-11(14(21)19(15)12(8)16(22)23)18-13(20)10(17)9-5-3-2-4-6-9/h2-6,10-11,15H,7,17H2,1H3,(H,18,20)(H,22,23)/t10-,11-,15?,25?/m1/s1
• InChIKey: GAMHLNJQISGSQF-KBHJFDKPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7R)-7-[(2R)-2-amino-2-phenylacetamido]-3-methyl-5,8-dioxo-5λ^4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: (7R)-7-[(2R)-2-amino-2-phenylacetamido]-3-methyl-5,8-dioxo-5λ^4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: [6R-[6α,7β(R*)]]-7-[(Aminophenylacetyl)amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid 5-Oxide; Cephalexin Sulfoxide

Database IDs

• CAS Number: 56193-21-6
• PubChem SID: 162258113
• PubChem CID: 71314641

CALCULATED PROPERTIES

• Acid pKa: 3.1632507
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -3.903818
• LogD (pH = 7.4): -4.251756
• Log P: -3.9023092
• Molar Refractivity: 90.4993 cm^3
• Polarizability: 35.21938 Å^3
• Polar Surface Area: 129.8 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C256820

Cephalosporin derivative with bactericidal activity.

REFERENCES

• Muggleton, et al.: Antimicrob. Agents Chemother., 253 (1968)
• Marrelli, L.P., et al.: Anal. Profiles Drug Subs., 4, 21 (1968)