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

• ChemBase ID: 176572
• Molecular Formular: C24H24N4O5S
• Molecular Mass: 480.53616
• Monoisotopic Mass: 480.14674089
• SMILES: c1cccc(c1)[C@H](C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)C)NC(=O)[C@H](N)c1ccccc1
• Canonical SMILES: O=C([C@@H](c1ccccc1)NC(=O)[C@@H](c1ccccc1)N)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)C
• InChI: InChI=1S/C24H24N4O5S/c1-13-12-34-23-18(22(31)28(23)19(13)24(32)33)27-21(30)17(15-10-6-3-7-11-15)26-20(29)16(25)14-8-4-2-5-9-14/h2-11,16-18,23H,12,25H2,1H3,(H,26,29)(H,27,30)(H,32,33)/t16-,17-,18-,23-/m1/s1
• InChIKey: KXWHDOPHWKBQHB-YTSMVRMISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2R)-2-[(2R)-2-amino-2-phenylacetamido]-2-phenylacetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: (6R,7R)-7-[(2R)-2-[(2R)-2-amino-2-phenylacetamido]-2-phenylacetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: (6R-trans)-D-2-Phenylglycyl-N-(2-carboxy-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-7-yl)-D-2-phenylglycinamide; Phenylglycylcefalexin; D-Phenylglycyl Cephalexin

Database IDs

• CAS Number: 72528-40-6
• PubChem SID: 164232482
• PubChem CID: 71751622

CALCULATED PROPERTIES

• Acid pKa: 3.400795
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -1.3107866
• LogD (pH = 7.4): -1.5650032
• Log P: -1.3136784
• Molar Refractivity: 126.135 cm^3
• Polarizability: 49.091145 Å^3
• Polar Surface Area: 141.83 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P327140

D-Phenylglycyl Cephalexin is an impurity of Cephalexin (C256800).

REFERENCES

• Hendrix, C. et al.: Arch. Pharm., 327, 215 (1994)
• Olsen, B.A. eyt al.: J. Chrom., 648, 165 (1994)