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

• ChemBase ID: 125616
• Molecular Formular: C5H7ClN2O3
• Molecular Mass: 178.57368
• Monoisotopic Mass: 178.01451977
• SMILES: ClC1=NO[C@H]([C@@H](C(=O)O)N)C1
• Canonical SMILES: N[C@H](C(=O)O)[C@@H]1CC(=NO1)Cl
• 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
• InChIKey: QAWIHIJWNYOLBE-OKKQSCSOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-2-[(5S)-3-chloro-4,5-dihydro-1,2-oxazol-5-yl]acetic acid
• IUPAC Traditional name: acivicin
• Synonyms: Antibiotic AT 125; Acivicin; (αS,5S)-α-Amino-3-chloro-4,5-dihydro-5-isoxazoleacetic Acid; [S-(R*,R*)]-α-Amino-3-chloro-4,5-dihydro-5-isoxazoleacetic Acid; AT 125; NSC 163501; U 42126; (+)-Acivicin

Database IDs

• CAS Number: 42228-92-2
• PubChem SID: 162219966
• PubChem CID: 294641
• Chemspider ID: 259938
• Wikipedia Title: Acivicin

CALCULATED PROPERTIES

• Acid pKa: 1.3971863
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -2.6740096
• LogD (pH = 7.4): -2.6993408
• Log P: -2.673843
• Molar Refractivity: 36.3964 cm^3
• Polarizability: 14.775068 Å^3
• Polar Surface Area: 84.91 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Off-White Solid
• Melting Point: >200°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A190150

Azaserine and Acivicin are classical and irreversible inhibitors of γ-Glutamyltranspeptidase (GGT).

REFERENCES

• Hanigan, M., et al.: Biochemistry, 32, 6302 (1993)
• Suzuki, H., et al.: J. Bacteriol., 175, 6038 (1993)
• Suzuki, H., et al.: J. Biol. Chem., 277, 43536 (1993)