CHEBI:74545 - acivicin

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ChEBI Name acivicin
ChEBI ID CHEBI:74545
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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C5H7ClN2O3
Net Charge 0
Average Mass 178.57400
Monoisotopic Mass 178.01452
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
SMILES [H][C@]1(CC(Cl)=NO1)[C@H](N)C(O)=O
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): 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 gamma-glutamyltransferase (EC 2.3.2.2).
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
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.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
(via L-alpha-amino acid )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
antileishmanial agent
An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
acivicin ChemIDplus
acivicine ChemIDplus
acivicino ChemIDplus
acivicinum ChemIDplus
Synonyms Sources
(α-S,5S)-α-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid ChemIDplus
S,5S)-α-amino-3-chloro-2-isoxazoline-5-acetic acid ChemIDplus
Antibiotic AT 125 ChemIDplus
AT 125 ChemIDplus
AT-125 ChemIDplus
NSC 163501 ChemIDplus
NSC-163501 ChemIDplus
U 42126 ChemIDplus
U-42,126 ChemIDplus
Manual Xrefs Databases
Acivicin Wikipedia
AVN PDBeChem
CPD0-1036 MetaCyc
D02755 KEGG DRUG
View more database links
Registry Numbers Types Sources
1074649 Reaxys Registry Number Reaxys
42228-92-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
03 November 2017