2-({4-[(5S)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl}(2-hydroxyethyl)amino)acetic acid

• ChemBase ID: 176831
• Molecular Formular: C16H20FN3O6
• Molecular Mass: 369.3449032
• Monoisotopic Mass: 369.1336136
• SMILES: N(c1ccc(cc1F)N1C[C@@H](OC1=O)CNC(=O)C)(CCO)CC(=O)O
• Canonical SMILES: OCCN(c1ccc(cc1F)N1C[C@@H](OC1=O)CNC(=O)C)CC(=O)O
• InChI: InChI=1S/C16H20FN3O6/c1-10(22)18-7-12-8-20(16(25)26-12)11-2-3-14(13(17)6-11)19(4-5-21)9-15(23)24/h2-3,6,12,21H,4-5,7-9H2,1H3,(H,18,22)(H,23,24)/t12-/m0/s1
• InChIKey: JGOXQNABWWZJSO-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-({4-[(5S)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl}(2-hydroxyethyl)amino)acetic acid
• IUPAC Traditional name: ({4-[(5S)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl}(2-hydroxyethyl)amino)acetic acid
• Synonyms: N-[4-[(5S)-5-[(Acetylamino)methyl]-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-N-(2-hydroxyethyl)glycine; PNU 142586

Database IDs

• CAS Number: 368891-70-7
• PubChem SID: 164232741
• PubChem CID: 71751720

CALCULATED PROPERTIES

• Acid pKa: 3.6611593
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -2.1933033
• LogD (pH = 7.4): -3.6776705
• Log P: -0.3569546
• Molar Refractivity: 87.7772 cm^3
• Polarizability: 33.337765 Å^3
• Polar Surface Area: 119.41 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P653405

PNU 142586 is an inactive metabolite of Linezolid (L466500).

REFERENCES

• Shinabarger, D., et al.: Antimicrob. Agents Chemother., 41, 2132 (1997)
• Wynalda, M., et al.: Drug Metab. Dispos., 28, 1014 (1997)