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CHEBI:74545 - acivicin

ChEBI IDCHEBI:74545
ChEBI Nameacivicin
Stars
DefinitionAn 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.
Last Modified3 November 2017
SubmitterGareth Owen
DownloadsMolfile
FormulaC5H7ClN2O3
Net Charge0
Average Mass178.575
Monoisotopic Mass178.01452
SMILES[H][C@@]1([C@H](N)C(=O)O)CC(Cl)=NO1
InChIInChI=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
InChIKeyQAWIHIJWNYOLBE-OKKQSCSOSA-N
Wikipedia
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
antimetabolite  A substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization.
EC 2.3.2.2 (gamma-glutamyltransferase) inhibitor  An EC 2.3.2.* (aminoacyltransferase) inhibitor that interferes with the action of γ-glutamyltransferase (EC 2.3.2.2).
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
glutamine antagonist  An antagonist that acts on glutamine receptors.
antileishmanial agent  An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:
antileishmanial agent  An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
acivicin (CHEBI:74545) has role antileishmanial agent (CHEBI:70868)
acivicin (CHEBI:74545) has role antimetabolite (CHEBI:35221)
acivicin (CHEBI:74545) has role antimicrobial agent (CHEBI:33281)
acivicin (CHEBI:74545) has role antineoplastic agent (CHEBI:35610)
acivicin (CHEBI:74545) has role EC 2.3.2.2 (γ-glutamyltransferase) inhibitor (CHEBI:74570)
acivicin (CHEBI:74545) has role glutamine antagonist (CHEBI:138931)
acivicin (CHEBI:74545) has role metabolite (CHEBI:25212)
acivicin (CHEBI:74545) is a isoxazoles (CHEBI:55373)
acivicin (CHEBI:74545) is a non-proteinogenic L-α-amino acid (CHEBI:83822)
acivicin (CHEBI:74545) is a organochlorine compound (CHEBI:36683)
IUPAC Name 
(2S)-amino[(5S)-3-chloro-4,5-dihydro-1,2-oxazol-5-yl]acetic acid
INNs  Source
acivicinChemIDplus
acivicineChemIDplus
acivicinoChemIDplus
acivicinumChemIDplus
Synonyms  Source
NSC 163501ChemIDplus
AT-125ChemIDplus
(α-S,5S)-α-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acidChemIDplus
NSC-163501ChemIDplus
(αS,5S)-α-amino-3-chloro-2-isoxazoline-5-acetic acidChemIDplus
U 42126ChemIDplus
Manual XrefsDatabases
AcivicinWikipedia
CPD0-1036MetaCyc
D02755KEGG DRUG
AVNPDBeChem
Registry NumbersSources
Reaxys:1074649Reaxys
CAS:42228-92-2ChemIDplus
Citations