Compound: Tabtoxin
SMILES: O=C1NC[C@@]1(O)CC[C@H](N)C(=O)N[C@H](C(=O)O)[C@H](O)C
InChIKey: BFSBNVPBVGFFCF-WDOVLDDZSA-N
Synonyms: Tabtoxin, 40957-90-2, Wildfire toxin, H3YX70R64N, (2S,3R)-2-[[(2S)-2-amino-4-[(3S)-3-hydroxy-2-oxoazetidin-3-yl]butanoyl]amino]-3-hydroxybutanoic acid, CHEBI:156429, DTXSID70961331, N-((2S)-2-Amino-4-((3S)-3-Hydroxy-2-oxo-3-azetidinyl)-1-oxobutyl)-L-threonine, L-Threonine, N-((2S)-2-amino-4-((3S)-3-Hydroxy-2-oxo-3-azetidinyl)-1-oxobutyl)-, (2S,3R)-2-(((2S)-2-amino-4-((3S)-3-hydroxy-2-oxoazetidin-3-yl)butanoyl)amino)-3-hydroxybutanoic acid, (2S,3R)-2-({(2S)-2-amino-4-[(3S)-3-hydroxy-2-oxoazetidin-3-yl]butanoyl}amino)-3-hydroxybutanoic acid, RefChem:932487, DTXCID201389162, (2S,3R)-2-(((2S)-2-azaniumyl-4-((3S)-3-hydroxy-2-oxoazetidin-3-yl)butanoyl)amino)-3-hydroxybutanoate, n-{(2s)-2-amino-4-[(3s)-3-hydroxy-2-oxoazetidin-3-yl]butanoyl}-l-threonine, beta-Tabtoxin, UNII-H3YX70R64N, WILDFIRE TOXIN [MI], orb1985276, CHEMBL3781539, SCHEMBL29388049, AKOS040754129, C20917, Q7673587, L-Threonine, 4-(3-hydroxy-2-oxo-3-azetidinyl)-L-2-aminobutanoyl-, (S)-
Theoretical properties:
molecular_formula: C11H19N3O6
molecular_weight: 289.29 g/mol
exact_mass: 289.12738533 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 6
hydrogen_bond_acceptor_count: 7
rotatable_bond_count: 7
heavy_atom_count: 20
topological_polar_surface_area: 162 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Tabtoxin is a monobactam phytotoxic dipeptide produced by Pseudomonas syringae, that causes wildfire disease in tobacco. It has a role as a toxin and a bacterial metabolite. It is a secondary alcohol, a dipeptide, a monobactam and a L-threonine derivative. It is functionally related to a tabtoxinine beta-lactam.
chebi: A monobactam phytotoxic dipeptide produced by <em>Pseudomonas syringae</em>, that causes wildfire disease in tobacco.
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Tabtoxin, also known as wildfire toxin, is a simple monobactam phytotoxin produced by Pseudomonas syringae. It is the precursor to the antibiotic tabtoxinine β-lactam (TBL). It is produced by:

Pseudomonas syringae pv. tabaci, the causal agent of the wildfire of tobacco.
P. syringae pv. coronafaciens
P. syringae pv. garcae
P. syringae BR2, causes a disease of bean (Phaseolus vulgaris) similar to tobacco wildfire. This organism is closely related to P. syringae pv. tabaci but cannot be classified in the pathovar tabaci because it is not pathogenic on tobacco.
Tabtoxin is a dipeptide precursor to the biologically active form of TBL, differing by having an extra threonine attached by a peptide bond to the C terminus. Tabtoxin is required by BR2(R) for both chlorosis and lesion formation on bean. All mutations that affected tabtoxin production, whether spontaneous deletion or transposon induced, also affected lesion formation, and in all cases, restoration of tabtoxin production also restored pathogenic symptoms. Other factors may be required for BR2 to be pathogenic on bean, but apparently these are in addition to tabtoxin production. TBL functions as a toxin by inhibition of glutamine synthetase.