Molecule ID: 6234

IUPAC Name: (4R)-4-amino-1,2-oxazolidin-3-one

Description: The molecule is a 4-amino-1,2-oxazolidin-3-one that has R configuration. It is an antibiotic produced by Streptomyces garyphalus or S. orchidaceus and is used as part of a multi-drug regimen for the treatment of tuberculosis when resistance to, or toxicity from, primary drugs has developed. An analogue of D-alanine, it interferes with bacterial cell wall synthesis in the cytoplasm by competitive inhibition of L-alanine racemase (which forms D-alanine from L-alanine) and D-alanine--D-alanine ligase (which incorporates D-alanine into the pentapeptide required for peptidoglycan formation and bacterial cell wall synthesis). It has a role as an antitubercular agent, an antiinfective agent, an antimetabolite, a metabolite and a NMDA receptor agonist. It is an organooxygen heterocyclic antibiotic, an organonitrogen heterocyclic antibiotic and a 4-amino-1,2-oxazolidin-3-one. It is a conjugate base of a D-cycloserine(1+). It is an enantiomer of a L-cycloserine. It is a tautomer of a D-cycloserine zwitterion.

SMILES: N[C@@H]1CON=C1O

SELFIES: [N][C@@H1][C][O][N][=C][Ring1][Branch1][O]

InChI: InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1

Molecular Properties:
- Polar Surface Area: 64.4 Ų
- LogP: -1.5