CHEBI:156430 - tabtoxinine β-lactam

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
This entity has been annotated by a third party. If you would like more information added to this entry, please contact ChEBI via email or GitHub.
ChEBI Name tabtoxinine β-lactam
ChEBI ID CHEBI:156430
ChEBI ASCII Name tabtoxinine beta-lactam
Definition A L-α-amino acid with a 3-hydroxy-2-oxoazetidin-propyl side chain. It is a monobactam antibiotic derived from tabtoxin with an inhibitory effect over glutamine synthetase.
Stars This entity has been manually annotated by a third party.
Submitter Martin Larralde
Supplier Information
Download Molfile XML SDF
Formula C7H12N2O4
Net Charge 0
Average Mass 188.183
Monoisotopic Mass 188.07971
InChI InChI=1S/C7H12N2O4/c8-4(5(10)11)1-2-7(13)3-9-6(7)12/h4,13H,1-3,8H2,(H,9,12)(H,10,11)/t4-,7-/m0/s1
InChIKey BSUXZTMOMIFYBF-FFWSUHOLSA-N
SMILES C1[C@](C(=O)N1)(CC[C@@H](C(=O)O)N)O
Metabolite of Species Details
Pseudomonas syringae (NCBI:txid317) See: PubMed
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): EC 6.3.1.2 (glutamate--ammonia ligase) inhibitor
An EC 6.3.* (C1N bond-forming ligase) inhibitor that interferes with the action of glutamateammonia ligase (EC 6.3.1.2).
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via heterocyclic antibiotic )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing tabtoxinine β-lactam (CHEBI:156430) has role apoptosis inducer (CHEBI:68495)
tabtoxinine β-lactam (CHEBI:156430) has role bacterial metabolite (CHEBI:76969)
tabtoxinine β-lactam (CHEBI:156430) has role EC 6.3.1.2 (glutamate—ammonia ligase) inhibitor (CHEBI:24319)
tabtoxinine β-lactam (CHEBI:156430) is a β-lactam antibiotic (CHEBI:27933)
tabtoxinine β-lactam (CHEBI:156430) is a monobactam (CHEBI:50695)
tabtoxinine β-lactam (CHEBI:156430) is a non-proteinogenic L-α-amino acid (CHEBI:83822)
tabtoxinine β-lactam (CHEBI:156430) is a tertiary α-hydroxy ketone (CHEBI:139592)
Incoming tabtoxin (CHEBI:156429) has functional parent tabtoxinine β-lactam (CHEBI:156430)
IUPAC Name
(S)-2-amino-4-((S)-3-hydroxy-2-oxoazetidin-3-yl)butanoic acid
Manual Xref Database
Tabtoxinine_%CE%B2-lactam Wikipedia accession
View more database links
Registry Number Type Source
65709-93-5 CAS Registry Number SUBMITTER
Citation Waiting for Citations Type Source
16662928 PubMed citation SUBMITTER