Structure via PubChem · Public domain (PubChem)
azaserine
Sign in to saveAzaserine is a naturally occurring toxic serine derivative diazo compound with antineoplastic and antibiotic properties deriving from its action as a purinergic antagonist and structural similarity to glutamine. Azaserine acts by competitively inhibiting glutamine amidotransferase, a key enzyme responsible for glutamine metabolism.
In the Vinony graph
Within Vinony's link graph, azaserine is referenced by 6 other articles, and connects out to antibiotic, digital object identifier and chemical formula.
Vinony files it under Antineoplastic drugs, Chemical pages without DrugBank identifier and Diazo compounds.
Its subject is documented across 6 Wikipedia language editions.
Chemical data
- Formula
- C5H7N3O4
- Molecular weight
- 173.13 g/mol
- IUPAC name
- (2S)-2-amino-3-[(2E)-2-diazoacetyl]oxypropanoic acid
- SMILES
- C([C@@H](C(=O)O)N)OC(=O)C=[N+]=[N-]
- InChIKey
- MZZGOOYMKKIOOX-VKHMYHEASA-N
- XLogP
- -3.2
- Polar surface area
- 91.6 Ų
- H-bond donors
- 2
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
859 papers- Azaserine.Antibiotics and chemotherapy · 1971
- Azaserine.IARC monographs on the evaluation of the carcinogenic risk of chemicals to man · 1976
- Azaserine, DON, and azotomycin: three diazo analogs of L-glutamine with clinical antitumor activity.Cancer treatment reports · 1979
- Azaserine: microbiological studies.Antibiotics & chemotherapy (Northfield, Ill.) · 1954
- Discovery of the Azaserine Biosynthetic Pathway Uncovers a Biological Route for α-Diazoester Production.Angewandte Chemie (International ed. in English) · 2023
via PubMed
Wikidata facts
- Mass
- 173.043655704
Show 5 more facts
- chemical formula
- C₅H₇N₃O₄
- canonical SMILES
- C(C(C(=O)O)N)OC(=O)C=[N+]=[N-]
- subject has role
- carcinogen
- isomeric SMILES
- C([C@@H](C(=O)O)N)OC(=O)C=[N+]=[N-]
- found in taxon
- Streptomyces
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Mechanism of Action
- Properties
- References
Azaserine is a naturally occurring toxic serine derivative diazo compound with antineoplastic and antibiotic properties deriving from its action as a purinergic antagonist and structural similarity to glutamine. Azaserine acts by competitively inhibiting glutamine amidotransferase, a key enzyme responsible for glutamine metabolism.
== Mechanism of Action ==
Excerpted from Wikipedia’s “azaserine” article, available under the CC BY-SA 4.0 licence.