EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:74545 - acivicin

Default Structure
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:
antileishmanial agent  An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
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.
glutamine antagonist  An antagonist that acts on glutamine receptors.
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).
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
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
Antibiotic AT 125ChemIDplus
AT 125ChemIDplus
AT-125ChemIDplus
NSC 163501ChemIDplus
NSC-163501ChemIDplus
U 42126ChemIDplus
Manual XrefsDatabases
AcivicinWikipedia
AVNPDBeChem
CPD0-1036MetaCyc
D02755KEGG DRUG
Registry NumbersSources
Reaxys:1074649Reaxys
CAS:42228-92-2ChemIDplus
Citations