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Chemical substance record

Acivicin

42228-92-2C5H7ClN2O3178.575 g/mol

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

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Identity & molecular properties

Source-linked values
CAS number42228-92-2ChEBI ↗
Molecular formulaC5H7ClN2O3ChEBI ↗
Molar mass178.575 g/molChEBI ↗
Monoisotopic mass178.01452 DaChEBI ↗
Formal charge0ChEBI ↗
ChEBI identifierCHEBI:74545ChEBI ↗

Cross-source molecular data

PubChem
Molar mass178.57 g/molPubChem ↗
Exact mass178.0145198 DaPubChem ↗
Computed XLogP-2.7PubChem ↗
Topological polar surface area (Ų)84.9PubChem ↗
H-bond donors2PubChem ↗
H-bond acceptors5PubChem ↗
Rotatable bonds2PubChem ↗

PubChem computed values are shown separately from the ChEBI record. An exact InChIKey match was used to connect the records. Molecular descriptors do not describe a supplied product’s purity, particle size or performance.

Names & structural identifiers

Copy any identifier
acivicin
(2S)-amino[(5S)-3-chloro-4,5-dihydro-1,2-oxazol-5-yl]acetic acid
QAWIHIJWNYOLBE-OKKQSCSOSA-N
[H][C@@]1([C@H](N)C(=O)O)CC(Cl)=NO1
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

Names & synonyms

(2S)-amino[(5S)-3-chloro-4,5-dihydro-1,2-oxazol-5-yl]acetic acidacivicineacivicinoacivicinum

Names are supplied by ChEBI. Trade names and related synonyms may describe a broader product context.

Classification & relationships

ChEBI ontology

Roles recorded in ChEBI

glutamine antagonistmetaboliteantimicrobial agentantimetaboliteantineoplastic agentantileishmanial agentEC 2.3.2.2 (gamma-glutamyltransferase) inhibitor

Database role annotations describe reported biological or chemical roles; they are not product approvals or recommendations for use.

Mass ↔ amount of substance

Calculated from sourced mass
Equivalent amount
0.00559989 mol

Uses 178.575 g/mol from ChEBI. Assumes the substance described by this record; no purity or concentration correction is applied.

Elemental composition

Theoretical mass fractions
C
Carbon · 5 atoms
33.63%
O
Oxygen · 3 atoms
26.88%
Cl
Chlorine · 1 atom
19.85%
N
Nitrogen · 2 atoms
15.69%
H
Hydrogen · 7 atoms
3.95%

Calculated theoretical mass fractions from the reported formula and PubChem periodic-table atomic masses. These are not assay or purity results.

Research & patent references

Selected source associations
Acivicin induces apoptosis independently of gamma-glutamyltranspeptidase activity. ↗Biochemical and biophysical research communications · 2001 Aug 3 · PMID 11478776
Acivicin induce filamentous growth of Saccharomyces cerevisiae. ↗Bioscience, biotechnology, and biochemistry · 2003 Oct · PMID 14586123

Sources & record history

Checked 27 Sep 2026
EMBL-EBI ChEBI · CHEBI:74545

Release 255, 9 September 2026. ChEBI three-star (manually annotated) source entry. View original record ↗ · CC BY 4.0

NCBI PubChem · CID 294641 · retrieved 2026-09-27

PubCAS formats source data, connects references and computes explicitly labelled conversions. CAS cross-references are supplied by ChEBI; they do not constitute CAS verification or endorsement.