CHEBI:74846 - azaserine

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ChEBI Name azaserine
ChEBI ID CHEBI:74846
Definition A carboxylic ester resulting from the formal condensation of the carboxy group of diazoacetic acid with the alcoholic hydroxy group of L-serine. An antibiotic produced by a Streptomyces species.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C5H7N3O4
Net Charge 0
Average Mass 173.12680
Monoisotopic Mass 173.04366
InChI InChI=1S/C5H7N3O4/c6-3(5(10)11)2-12-4(9)1-8-7/h1,3H,2,6H2,(H,10,11)/t3-/m0/s1
InChIKey MZZGOOYMKKIOOX-VKHMYHEASA-N
SMILES N[C@@H](COC(=O)C=[N+]=[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.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
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.
immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
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.
immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing azaserine (CHEBI:74846) has role antifungal agent (CHEBI:35718)
azaserine (CHEBI:74846) has role antimetabolite (CHEBI:35221)
azaserine (CHEBI:74846) has role antimicrobial agent (CHEBI:33281)
azaserine (CHEBI:74846) has role antineoplastic agent (CHEBI:35610)
azaserine (CHEBI:74846) has role glutamine antagonist (CHEBI:138931)
azaserine (CHEBI:74846) has role immunosuppressive agent (CHEBI:35705)
azaserine (CHEBI:74846) has role metabolite (CHEBI:25212)
azaserine (CHEBI:74846) is a L-serine derivative (CHEBI:84135)
azaserine (CHEBI:74846) is a carboxylic ester (CHEBI:33308)
azaserine (CHEBI:74846) is a diazo compound (CHEBI:39444)
azaserine (CHEBI:74846) is a non-proteinogenic L-α-amino acid (CHEBI:83822)
IUPAC Name
O-(diazoacetyl)-L-serine
INNs Sources
azaserina ChemIDplus
azaserine ChemIDplus
azasérine WHO MedNet
azaserinum ChemIDplus
Synonyms Sources
L-azaserine ChemIDplus
L-β-(diazoacetoxy)alanin ChemIDplus
L-β-(diazoacetoxy)alanine ChEBI
L-serine diazoacetate ChemIDplus
L-serine diazoacetate ester ChemIDplus
Manual Xrefs Databases
Azaserine Wikipedia
AZS PDBeChem
C19194 KEGG COMPOUND
D03032 KEGG DRUG
L-AZASERINE MetaCyc
US2996435 Patent
US3030388 Patent
View more database links
Registry Number Type Source
115-02-6 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
19136606 PubMed citation Europe PMC
23101568 PubMed citation Europe PMC
23301939 PubMed citation Europe PMC
4951003 PubMed citation Europe PMC
7048085 PubMed citation Europe PMC
791808 PubMed citation Europe PMC
Last Modified
03 November 2017