CHEBI:74846 - azaserine

ChEBI IDCHEBI:74846
ChEBI Nameazaserine
Stars
DefinitionA 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.
Last Modified3 November 2017
SubmitterGareth Owen
DownloadsMolfile
FormulaC5H7N3O4
Net Charge0
Average Mass173.128
Monoisotopic Mass173.04366
SMILES[N-]=[N+]=CC(=O)OC[C@H](N)C(=O)O
InChIInChI=1S/C5H7N3O4/c6-3(5(10)11)2-12-4(9)1-8-7/h1,3H,2,6H2,(H,10,11)/t3-/m0/s1
InChIKeyMZZGOOYMKKIOOX-VKHMYHEASA-N
Wikipedia
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
glutamine antagonist  An antagonist that acts on glutamine receptors.
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.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
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.
Applications:
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.
ChEBI Ontology
Outgoing Relation(s)
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  Source
azaserinumChemIDplus
azaserinaChemIDplus
azaserineChemIDplus
azasérineWHO MedNet
Synonyms  Source
L-serine diazoacetate esterChemIDplus
L-serine diazoacetateChemIDplus
L-azaserineChemIDplus
L-β-(diazoacetoxy)alanineChEBI
L-β-(diazoacetoxy)alaninChemIDplus
Manual XrefsDatabases
AzaserineWikipedia
C19194KEGG COMPOUND
D03032KEGG DRUG
AZSPDBeChem
L-AZASERINEMetaCyc
US2996435Patent
US3030388Patent
Registry NumbersSources
CAS:115-02-6ChemIDplus
CAS:115-02-6KEGG COMPOUND
Citations