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

• ChemBase ID: 163977
• Molecular Formular: C16H17N3O4S
• Molecular Mass: 347.38888
• Monoisotopic Mass: 347.09397704
• SMILES: c1cccc(c1)[C@H](C(=O)N[C@@H]1C(=O)N2[C@@H]1SC=C(C2C(=O)O)C)N
• Canonical SMILES: N[C@H](c1ccccc1)C(=O)N[C@@H]1C(=O)N2[C@@H]1SC=C(C2C(=O)O)C
• InChI: InChI=1S/C16H17N3O4S/c1-8-7-24-15-11(14(21)19(15)12(8)16(22)23)18-13(20)10(17)9-5-3-2-4-6-9/h2-7,10-12,15H,17H2,1H3,(H,18,20)(H,22,23)/t10-,11-,12?,15-/m1/s1
• InChIKey: UALOAEFJDPITFY-XOGJBXBPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2R)-2-amino-2-phenylacetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid
• IUPAC Traditional name: (6R,7R)-7-[(2R)-2-amino-2-phenylacetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid
• Synonyms: (6R,7R)-7-[[(2R)-Aminophenylacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic Acid; Cephalexin Impurity F; Delta 2 Cephalexin; [6R-[6α,7β(R*)]]-7-[(Aminophenylacetyl)amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic Acid; Δ2-Cephalexin

Database IDs

• CAS Number: 79750-46-2
• PubChem SID: 162258112
• PubChem CID: 14031068

CALCULATED PROPERTIES

• Acid pKa: 3.1449423
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.2360756
• LogD (pH = 7.4): -2.4912856
• Log P: -2.236275
• Molar Refractivity: 87.69 cm^3
• Polarizability: 34.630867 Å^3
• Polar Surface Area: 112.73 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C256810

Δ2-Cephalexin is an isomeric impurity of the semi-synthetic antibiotic Cephalexin (C256800).

REFERENCES

• Marincel, J. et al.: Acta Pharmacol Jugo., 38, 35 (1988)
• Hendrix, C. et al.: Arck. Pharm., 327, 215 (1988)