Marvin  07041312482D          

 12 12  0  0  1  0            999 V2000
    4.2917   -4.3368    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6317   -4.8191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0632   -3.5372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9844   -4.3368    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2382   -3.5372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7559   -2.8772    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.8858   -4.0218    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0080   -4.7461    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0080   -5.5711    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7187   -4.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7187   -3.5023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4422   -4.7461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  1  7  1  6  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  5  4  2  0  0  0  0
  6  5  1  0  0  0  0
  8  9  1  1  0  0  0
 10  8  1  0  0  0  0
 11 10  2  0  0  0  0
 12 10  1  0  0  0  0
  8  1  1  0  0  0  0
M  END
> <ID>
CHEBI:74545

> <NAME>
acivicin

> <DEFINITION>
An L-α-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.

> <STAR>
3

> <SYNONYM>
U-42,126; U 42126; NSC-163501; NSC 163501; AT-125; AT 125; Antibiotic AT 125; (alphaS,5S)-alpha-amino-3-chloro-2-isoxazoline-5-acetic acid; (alpha-S,5S)-alpha-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid

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

> <INN>
acivicinum; acivicino; acivicine; acivicin

> <FORMULA>
C5H7ClN2O3

> <MASS>
178.57400

> <MONOISOTOPIC_MASS>
178.01452

> <CHARGE>
0

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

> <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

> <CAS_REGISTRY_NUMBER>
42228-92-2

> <REAXYS_REGISTRY_NUMBER>
1074649

> <CHEMIDPLUS>
42228-92-2

> <KEGG_DRUG_ACCESSION>
D02755

> <METACYC_ACCESSION>
CPD0-1036

> <PDBECHEM_ACCESSION>
AVN

> <WIKIPEDIA_ACCESSION>
Acivicin

> <PUBMED_CITATION>
11478776; 14586123; 2383250; 2894949; 3112985; 3165971; 3710919; 3915184; 6102405; 7026076; 7150366; 8060335; 9829740

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