(7S)-7-[(2R)-2-amino-2-phenylacetamido]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 172382
• Molecular Formular: C16H16ClN3O4
• Molecular Mass: 349.76894
• Monoisotopic Mass: 349.08293369
• SMILES: C12N(C(=C(CC1)Cl)C(=O)O)C(=O)[C@H]2NC(=O)[C@H](N)c1ccccc1
• Canonical SMILES: N[C@H](c1ccccc1)C(=O)N[C@H]1C2CCC(=C(N2C1=O)C(=O)O)Cl
• InChI: InChI=1S/C16H16ClN3O4/c17-9-6-7-10-12(15(22)20(10)13(9)16(23)24)19-14(21)11(18)8-4-2-1-3-5-8/h1-5,10-12H,6-7,18H2,(H,19,21)(H,23,24)/t10?,11-,12+/m1/s1
• InChIKey: JAPHQRWPEGVNBT-SAIIYOCFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7S)-7-[(2R)-2-amino-2-phenylacetamido]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: (7S)-7-[(2R)-2-amino-2-phenylacetamido]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: (6R,7S)-7-[[(2R)-2-Amino-2-phenylacetyl]amino]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; Lorabid; Loracarbef

Database IDs

• CAS Number: 76470-66-1
• PubChem SID: 164228292
• PubChem CID: 9864042

CALCULATED PROPERTIES

• Acid pKa: 3.1261737
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.3995888
• LogD (pH = 7.4): -2.6549032
• Log P: -2.3996444
• Molar Refractivity: 86.6375 cm^3
• Polarizability: 33.446136 Å^3
• Polar Surface Area: 112.73 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L469550

An antibiotic, a synthetic carbacephem analogue of cefaclor, and is more stable chemically.

REFERENCES

• Biedenbach, D., et al.: J. Clin. Microbiol., 32, 559 (1994)