acivicin (CHEBI:74545)

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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.

Supplier Information	ChemicalBook:CB5755462, eMolecules:476205, ZINC000000388314

Download	Molfile XML SDF

Wikipedia	License
Acivicin is an analog of glutamine. It is an inhibitor of gamma-glutamyl transferase. It is a fermentation product of Streptomyces sviceus. It interferes with glutamate metabolism and inhibits glutamate dependent synthesis of enzymes, and is thereby potentially helpful in treatment of solid tumors. After its discovery in 1972, acivicin was studied as an anti-cancer agent, but trials were unsuccessful due to toxicity.
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Formula

C5H7ClN2O3

Net Charge

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.

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.

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

Synonyms	Sources
(α-S,5S)-α-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid	ChemIDplus
(αS,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

Citations

Last Modified

03 November 2017