Molecule ID: 294641

IUPAC Name: (2S)-2-amino-2-[(5S)-3-chloro-4,5-dihydro-1,2-oxazol-5-yl]acetic acid

Description: The molecule is an L-alpha-amino acid that is L-alanine in which the methyl group is replaced by a (5S)-3-chloro-4,5-dihydro-1,2-oxazol-5-yl group. A glutamine analogue antimetabolite, it interferes with glutamate metabolism and several glutamate-dependent synthetic enzymes. It is obtained as a fermentation product of Streptomyces sviceus bacteria. It has a role as an antimetabolite, a metabolite, an antineoplastic agent, an EC 2.3.2.2 (gamma-glutamyltransferase) inhibitor, an antimicrobial agent, an antileishmanial agent and a glutamine antagonist. It is a member of isoxazoles, an organochlorine compound and a non-proteinogenic L-alpha-amino acid.

SMILES: N[C@H](C(=O)O)[C@@H]1CC(Cl)=NO1

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

InChI: InChI=1S/C5H7ClN2O3/c6-3-1-2(11-8-3)4(7)5(9)10/h2,4H,1,7H2,(H,9,10)/t2-,4-/m0/s1

Molecular Properties:
- Polar Surface Area: 84.9 Ų
- LogP: -2.7