acivicin

CHEBI:74545 ·resolve ·ANTIPROTOZOAL ·EXACT SEEDED

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. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:36683 CHEBI:36683
CHEBI:55373 CHEBI:55373
CHEBI:83822 CHEBI:83822

Chemical structure

Computed structure properties
Molecular formula	C5H7ClN2O3
Charge	0
Average mass	178.575 Da
Monoisotopic mass	178.01452 Da
Source	ChEBI
InChIKey	QAWIHIJWNYOLBE-OKKQSCSOSA-N

SMILES

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

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

Also called

acivicine (INN)— chebi
acivicino (INN)— chebi
acivicinum (INN)— chebi
(2S)-amino[(5S)-3-chloro-4,5-dihydro-1,2-oxazol-5-yl]acetic acid (EXACT_SYNONYM)— chebi
(α-S,5S)-α-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid (EXACT_SYNONYM)— chebi
(αS,5S)-α-amino-3-chloro-2-isoxazoline-5-acetic acid (EXACT_SYNONYM)— chebi
AT 125 (EXACT_SYNONYM)— chebi
AT-125 (EXACT_SYNONYM)— chebi
Antibiotic AT 125 (EXACT_SYNONYM)— chebi
NSC 163501 (EXACT_SYNONYM)— chebi
NSC-163501 (EXACT_SYNONYM)— chebi
U 42126 (EXACT_SYNONYM)— chebi
U-42,126 (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:42228-92-2
kegg.drug:D02755
metacyc.compound:CPD0-1036
pdb-ccd:AVN
reaxys:1074649
wikipedia.en:Acivicin

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:33281 CHEBI:33281
CHEBI:70868 CHEBI:70868

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:74545`	acivicin	`antibioticmech:chebi-407396530d`	2026-08-30

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.