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.

Label unavailable CHEBI:36683
Label unavailable CHEBI:55373
Label unavailable 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

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

kegg.drug:D02755

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

wikipedia.en:Acivicin

Activity roles

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

antimicrobial agent CHEBI:33281
antileishmanial agent 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
RESEEDED_FROM_SOURCES 2026-09-10 · 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 (YAML).

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