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

• ChemBase ID: 176830
• Molecular Formular: C16H20FN3O6
• Molecular Mass: 369.3449032
• Monoisotopic Mass: 369.1336136
• SMILES: N(c1ccc(cc1F)N1C[C@@H](OC1=O)CNC(=O)C)CCOCC(=O)O
• Canonical SMILES: CC(=O)NC[C@H]1CN(C(=O)O1)c1ccc(c(c1)F)NCCOCC(=O)O
• InChI: InChI=1S/C16H20FN3O6/c1-10(21)19-7-12-8-20(16(24)26-12)11-2-3-14(13(17)6-11)18-4-5-25-9-15(22)23/h2-3,6,12,18H,4-5,7-9H2,1H3,(H,19,21)(H,22,23)/t12-/m0/s1
• InChIKey: GEFZWBCMTWREOP-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[2-({4-[(5S)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl}amino)ethoxy]acetic acid
• IUPAC Traditional name: [2-({4-[(5S)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl}amino)ethoxy]acetic acid
• Synonyms: N-[4-[(5S)-5-[(Acetylamino)methyl]-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-N-(2-hydroxyethyl)glycine; PNU 142300

Database IDs

• CAS Number: 368891-69-4
• PubChem SID: 164232740
• PubChem CID: 71751719

CALCULATED PROPERTIES

• Acid pKa: 3.6575322
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -2.3079321
• LogD (pH = 7.4): -3.7135267
• Log P: -0.6102082
• Molar Refractivity: 88.2936 cm^3
• Polarizability: 33.405357 Å^3
• Polar Surface Area: 117.2 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P653400

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)