tabtoxin (CHEBI:156429)

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ChEBI Name	tabtoxin

ChEBI ID	CHEBI:156429

Definition	A monobactam phytotoxic dipeptide produced by Pseudomonas syringae, that causes wildfire disease in tobacco.

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	Martin Larralde

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Formula

C11H19N3O6

Net Charge

Average Mass

289.288

Monoisotopic Mass

289.12739

InChI

InChI=1S/C11H19N3O6/c1-5(15)7(9(17)18)14-8(16)6(12)2-3-11(20)4-13-10(11)19/h5-7,15,20H,2-4,12H2,1H3,(H,13,19)(H,14,16)(H,17,18)/t5-,6+,7+,11+/m1/s1

InChIKey

BFSBNVPBVGFFCF-WDOVLDDZSA-N

SMILES

C[C@@H](O)[C@H](NC(=O)[C@@H](N)CC[C@]1(O)CNC1=O)C(O)=O

Metabolite of Species	Details
Pseudomonas coronafaciens pv. coronafaciens (NCBI:txid235275)	See: PubMed
Pseudomonas amygdali pv. tabaci (NCBI:txid322)	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 )

Biological Role(s):	bacterial metabolite Any prokaryotic metabolite produced during a metabolic reaction in bacteria. toxin Poisonous substance produced by a biological organism such as a microbe, animal or plant. antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. (via heterocyclic antibiotic )

ChEBI Ontology
Outgoing	tabtoxin (CHEBI:156429) has functional parent tabtoxinine β-lactam (CHEBI:156430) tabtoxin (CHEBI:156429) has role bacterial metabolite (CHEBI:76969) tabtoxin (CHEBI:156429) has role toxin (CHEBI:27026) tabtoxin (CHEBI:156429) is a L-threonine derivative (CHEBI:84189) tabtoxin (CHEBI:156429) is a dipeptide (CHEBI:46761) tabtoxin (CHEBI:156429) is a monobactam (CHEBI:50695) tabtoxin (CHEBI:156429) is a secondary alcohol (CHEBI:35681)

IUPAC Name

N-{(2S)-2-amino-4-[(3S)-3-hydroxy-2-oxoazetidin-3-yl]butanoyl}-L-threonine

Synonyms	Sources
(2S,3R)-2-({(2S)-2-amino-4-[(3S)-3-hydroxy-2-oxoazetidin-3-yl]butanoyl}amino)-3-hydroxybutanoic acid	IUPAC
N-((2S)-2-amino-4-((3S)-3-hydroxy-2-oxo-3-azetidinyl)-1-oxobutyl)-L-threonine	ChemIDplus
wildfire toxin	ChEBI

Registry Number	Type	Source
40957-90-2	CAS Registry Number	ChemIDplus

Last Modified

18 November 2020