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

• ChemBase ID: 163976
• Molecular Formular: C16H17N3O4S
• Molecular Mass: 347.38888
• Monoisotopic Mass: 347.09397704
• SMILES: c1cccc(c1)[C@@H](C(=O)N[C@@H]1C(=O)N2C1SCC(=C2C(=O)O)C)N
• Canonical SMILES: N[C@@H](c1ccccc1)C(=O)N[C@@H]1C(=O)N2C1SCC(=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/h2-6,10-11,15H,7,17H2,1H3,(H,18,20)(H,22,23)/t10-,11+,15?/m0/s1
• InChIKey: ZAIPMKNFIOOWCQ-FEBOZLGHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7R)-7-[(2S)-2-amino-2-phenylacetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: (7R)-7-[(2S)-2-amino-2-phenylacetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: (6R,7R)-7-[[(2S)-2-amino-2-phenylacetyl]amino]-3-methyl-8-oxo-5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; [6R-[6α,7β(S*)]]-7-[(Aminophenylacetyl)amino]-3-methyl-8-oxo-5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; 7-(α-Amino-L-phenylacetamido)-3-deacetoxycephalosporanic Acid; L-Cephalexin

Database IDs

• CAS Number: 34632-04-7
• PubChem SID: 162258111
• PubChem CID: 44318507

CALCULATED PROPERTIES

• Acid pKa: 3.4520106
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.1413963
• LogD (pH = 7.4): -2.3951817
• Log P: -2.145041
• Molar Refractivity: 88.9736 cm^3
• Polarizability: 34.625595 Å^3
• Polar Surface Area: 112.73 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C256805

The L-diastereomer of the β-lactam antibiotic Cephalexin (C256800). It is is transported by PEPT1 (the oligopeptide transporter responsible for absorption of peptide nutrients in the small intestine) with high affinity, but is not metabolized by PEPT1 its

REFERENCES

• Mitsuoka, K. et al.: Biol. Pharmac. Bull., 32, 1459 (2009)
• Snyder, N.J. et al.: Antimicrob. Agents Chemother., 41, 1649 (2009)