NP-MRD: Showing NP-Card for (2s,3r)-2-{[(2s)-2-amino-4-[(3s)-2,3-dihydroxy-4h-azet-3-yl]-1-hydroxybutylidene]amino}-3-hydroxybutanoic acid (NP0163068)

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Record Information

Version

2.0

Created at

2022-09-02 21:36:25 UTC

Updated at

2022-09-02 21:36:25 UTC

NP-MRD ID

NP0163068

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r)-2-{[(2s)-2-amino-4-[(3s)-2,3-dihydroxy-4h-azet-3-yl]-1-hydroxybutylidene]amino}-3-hydroxybutanoic acid

Description

Tabtoxin, also known as wildfire toxin, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Tabtoxin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (2s,3r)-2-{[(2s)-2-amino-4-[(3s)-2,3-dihydroxy-4h-azet-3-yl]-1-hydroxybutylidene]amino}-3-hydroxybutanoic acid is found in Pseudomonas syringae. (2s,3r)-2-{[(2s)-2-amino-4-[(3s)-2,3-dihydroxy-4h-azet-3-yl]-1-hydroxybutylidene]amino}-3-hydroxybutanoic acid was first documented in 2011 (PMID: 22069758). Based on a literature review a significant number of articles have been published on tabtoxin (PMID: 35510837) (PMID: 29307827) (PMID: 28403565) (PMID: 29733155) (PMID: 23770908) (PMID: 22994681).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 39  0  0  0  0  0  0  0  0999 V2000
   -3.0899    2.1395    1.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9626    0.9665    0.6319 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3123    1.1153   -0.7261 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1721   -0.3375    0.7867 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9790   -0.3230   -0.0045 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9106   -0.9830    0.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9066   -1.7615    1.4228 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2413   -0.8841   -0.6105 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0172   -0.0178   -1.7187 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5089   -0.4277    0.0898 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5952   -0.3759   -0.9489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9243    0.0659   -0.3952 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8810    0.0897   -1.4158 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4216   -0.6276    0.7993 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3956    0.6508    1.4117 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9705    1.2558    0.3969 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6623    2.6087    0.1579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0071   -1.4831    0.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1193   -1.7256    0.8837 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5973   -2.3307   -0.6712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4141    2.5648    1.9835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1500    2.9376    0.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0420    1.7908    1.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8668    0.9536    1.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9122    0.3722   -1.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9219   -0.4368    1.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5239   -1.3771    2.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4627   -1.9243   -0.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4983   -0.3952   -2.5469 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2902    0.9479   -1.4679 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3786    0.5035    0.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7489   -1.2179    0.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7342   -1.3892   -1.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3410    0.2974   -1.7924 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5330    0.7530   -2.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4319   -1.0849    0.6803 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7273   -1.3326    1.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4445    3.2338   -0.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2864   -2.8113   -1.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  6
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
  4 18  1  0
 18 20  1  0
 18 19  2  0
 16 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  1
  3 25  1  0
  4 26  1  1
  7 27  1  0
  8 28  1  6
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 17 38  1  0
 20 39  1  0
M  END


  Mrv1652309022223362D          

 20 20  0  0  1  0            999 V2000
    0.5116    6.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7251    5.3501    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5220    5.1366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1418    4.7668    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3553    3.9699    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2281    3.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0250    3.6001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0146    2.5896    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5979    2.0063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7823    2.3761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9959    1.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.9959    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1709    1.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9959    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.1709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1709    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9959    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6551    4.9803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2385    4.3969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8687    5.7772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  1  0  0  0
  2  4  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  2  0  0  0  0
  6  7  1  4  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
  4 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0163068

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](O)[C@H](N=C(O)[C@@H](N)CC[C@]1(O)CN=C1O)C(O)=O

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
BFSBNVPBVGFFCF-WDOVLDDZSA-N

> <FORMULA>
C11H19N3O6

> <MOLECULAR_WEIGHT>
289.288

> <EXACT_MASS>
289.127385344

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
28.17111773739474

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R)-2-{[(2S)-2-amino-4-[(3S)-3,4-dihydroxy-2,3-dihydroazet-3-yl]-1-hydroxybutylidene]amino}-3-hydroxybutanoic acid

> <ALOGPS_LOGP>
-2.93

> <JCHEM_LOGP>
-4.843558787438739

> <ALOGPS_LOGS>
-2.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.193369700511474

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.0301500480735988

> <JCHEM_PKA_STRONGEST_BASIC>
9.310202430005807

> <JCHEM_POLAR_SURFACE_AREA>
168.95999999999998

> <JCHEM_REFRACTIVITY>
66.39880000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.52e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tabtoxin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       0.955  11.474   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.354   9.987   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.841   9.588   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.265   8.898   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       0.663   7.410   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -0.426   6.322   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.913   6.720   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.027   4.834   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -1.116   3.745   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       1.460   4.435   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.859   2.948   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.770   1.859   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.319   2.948   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.859   0.770   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       0.770  -0.319   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      -0.319   0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.859   0.770   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.223   9.297   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.312   8.208   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.621  10.784   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   18                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   16                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12   17                                                  
CONECT   17   16                                                            
CONECT   18    4   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R)-2-({(2S)-2-amino-4-[(3S)-3-hydroxy-2-oxoazetidin-3-yl]butanoyl}amino)-3-hydroxybutanoic acid	ChEBI
N-((2S)-2-Amino-4-((3S)-3-hydroxy-2-oxo-3-azetidinyl)-1-oxobutyl)-L-threonine	ChEBI
Wildfire toxin	ChEBI
(2S,3R)-2-({(2S)-2-amino-4-[(3S)-3-hydroxy-2-oxoazetidin-3-yl]butanoyl}amino)-3-hydroxybutanoate	Generator

Chemical Formula

C₁₁H₁₉N₃O₆

Average Mass

289.2880 Da

Monoisotopic Mass

289.12739 Da

IUPAC Name

(2S,3R)-2-{[(2S)-2-amino-4-[(3S)-3,4-dihydroxy-2,3-dihydroazet-3-yl]-1-hydroxybutylidene]amino}-3-hydroxybutanoic acid

Traditional Name

tabtoxin

CAS Registry Number

Not Available

SMILES

C[C@@H](O)[C@H](N=C(O)[C@@H](N)CC[C@]1(O)CN=C1O)C(O)=O

InChI Identifier

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

InChI Key

BFSBNVPBVGFFCF-WDOVLDDZSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pseudomonas syringae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Monobactam
N-acyl-l-alpha-amino acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
Beta-hydroxy acid
Heterocyclic fatty acid
Hydroxy fatty acid
Short-chain hydroxy acid
Fatty amide
Hydroxy acid
N-acyl-amine
Fatty acyl
Fatty acid
Tertiary alcohol
Beta-lactam
Secondary carboxylic acid amide
Secondary alcohol
Amino acid or derivatives
Azetidine
Carboxamide group
Amino acid
Lactam
Organoheterocyclic compound
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Alcohol
Organooxygen compound
Amine
Carbonyl group
Organic nitrogen compound
Organopnictogen compound
Primary amine
Organic oxygen compound
Organonitrogen compound
Organic oxide
Hydrocarbon derivative
Primary aliphatic amine
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.9	ALOGPS
logP	-4.8	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	1.03	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	168.96 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	66.4 m³·mol⁻¹	ChemAxon
Polarizability	28.17 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

96964

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tabtoxin

METLIN ID

Not Available

PubChem Compound

107817

PDB ID

Not Available

ChEBI ID

156429

Good Scents ID

Not Available

References

General References

Lyu J, Ushimaru R, Abe I: Characterization of Enzymes Catalyzing the Initial Steps of the beta-Lactam Tabtoxin Biosynthesis. Org Lett. 2022 May 13;24(18):3337-3341. doi: 10.1021/acs.orglett.2c00878. Epub 2022 May 5. [PubMed:35510837 ]
Manning ME, Danson EJ, Calderone CT: Functional chararacterization of the enzymes TabB and TabD involved in tabtoxin biosynthesis by Pseudomonas syringae. Biochem Biophys Res Commun. 2018 Jan 29;496(1):212-217. doi: 10.1016/j.bbrc.2018.01.028. Epub 2018 Jan 4. [PubMed:29307827 ]
Carezzano ME, Sotelo JP, Primo E, Reinoso EB, Paletti Rovey MF, Demo MS, Giordano WF, Oliva MLM: Inhibitory effect of Thymus vulgaris and Origanum vulgare essential oils on virulence factors of phytopathogenic Pseudomonas syringae strains. Plant Biol (Stuttg). 2017 Jul;19(4):599-607. doi: 10.1111/plb.12572. Epub 2017 May 14. [PubMed:28403565 ]
Cheng DD, Sun JP, Chai Y, Zhu YY, Zhao M, Sun GY, Sun XB: [Effects of Pseudomonas syringae pv. tabaci infection on tobacco photosynthetic apparatus under light or dark conditions.]. Ying Yong Sheng Tai Xue Bao. 2016 Aug;27(8):2655-2662. doi: 10.13287/j.1001-9332.201608.006. [PubMed:29733155 ]
Arai T, Arimura Y, Ishikura S, Kino K: L-amino acid ligase from Pseudomonas syringae producing tabtoxin can be used for enzymatic synthesis of various functional peptides. Appl Environ Microbiol. 2013 Aug;79(16):5023-9. doi: 10.1128/AEM.01003-13. Epub 2013 Jun 14. [PubMed:23770908 ]
Wencewicz TA, Walsh CT: Pseudomonas syringae self-protection from tabtoxinine-beta-lactam by ligase TblF and acetylase Ttr. Biochemistry. 2012 Oct 2;51(39):7712-25. doi: 10.1021/bi3011384. Epub 2012 Sep 19. [PubMed:22994681 ]
Kong HS, Roberts DP, Patterson CD, Kuehne SA, Heeb S, Lakshman DK, Lydon J: Effect of overexpressing rsmA from Pseudomonas aeruginosa on virulence of select phytotoxin-producing strains of P. syringae. Phytopathology. 2012 Jun;102(6):575-87. doi: 10.1094/PHYTO-09-11-0267. [PubMed:22568815 ]
Arrebola E, Cazorla FM, Perez-Garcia A, de Vicente A: Chemical and metabolic aspects of antimetabolite toxins produced by Pseudomonas syringae pathovars. Toxins (Basel). 2011 Sep;3(9):1089-110. doi: 10.3390/toxins3091089. Epub 2011 Aug 31. [PubMed:22069758 ]
Duke SO, Dayan FE: Modes of action of microbially-produced phytotoxins. Toxins (Basel). 2011 Aug;3(8):1038-1064. doi: 10.3390/toxins3081038. Epub 2011 Aug 22. [PubMed:22069756 ]
Yang HJ, Lee JS, Cha JY, Baik HS: Negative regulation of pathogenesis in Pseudomonas syringae pv. tabaci 11528 by ATP-dependent Lon protease. Mol Cells. 2011 Oct;32(4):317-23. doi: 10.1007/s10059-011-1017-3. Epub 2011 Sep 6. [PubMed:21904881 ]
LOTUS database [Link]

Showing NP-Card for (2s,3r)-2-{[(2s)-2-amino-4-[(3s)-2,3-dihydroxy-4h-azet-3-yl]-1-hydroxybutylidene]amino}-3-hydroxybutanoic acid (NP0163068)

MOL for NP0163068 ((2s,3r)-2-{[(2s)-2-amino-4-[(3s)-2,3-dihydroxy-4h-azet-3-yl]-1-hydroxybutylidene]amino}-3-hydroxybutanoic acid)

3D MOL for NP0163068 ((2s,3r)-2-{[(2s)-2-amino-4-[(3s)-2,3-dihydroxy-4h-azet-3-yl]-1-hydroxybutylidene]amino}-3-hydroxybutanoic acid)

3D SDF for NP0163068 ((2s,3r)-2-{[(2s)-2-amino-4-[(3s)-2,3-dihydroxy-4h-azet-3-yl]-1-hydroxybutylidene]amino}-3-hydroxybutanoic acid)

3D-SDF for NP0163068 ((2s,3r)-2-{[(2s)-2-amino-4-[(3s)-2,3-dihydroxy-4h-azet-3-yl]-1-hydroxybutylidene]amino}-3-hydroxybutanoic acid)

PDB for NP0163068 ((2s,3r)-2-{[(2s)-2-amino-4-[(3s)-2,3-dihydroxy-4h-azet-3-yl]-1-hydroxybutylidene]amino}-3-hydroxybutanoic acid)

3D PDB for NP0163068 ((2s,3r)-2-{[(2s)-2-amino-4-[(3s)-2,3-dihydroxy-4h-azet-3-yl]-1-hydroxybutylidene]amino}-3-hydroxybutanoic acid)

SMILES for NP0163068 ((2s,3r)-2-{[(2s)-2-amino-4-[(3s)-2,3-dihydroxy-4h-azet-3-yl]-1-hydroxybutylidene]amino}-3-hydroxybutanoic acid)

INCHI for NP0163068 ((2s,3r)-2-{[(2s)-2-amino-4-[(3s)-2,3-dihydroxy-4h-azet-3-yl]-1-hydroxybutylidene]amino}-3-hydroxybutanoic acid)

Structure for NP0163068 ((2s,3r)-2-{[(2s)-2-amino-4-[(3s)-2,3-dihydroxy-4h-azet-3-yl]-1-hydroxybutylidene]amino}-3-hydroxybutanoic acid)

3D Structure for NP0163068 ((2s,3r)-2-{[(2s)-2-amino-4-[(3s)-2,3-dihydroxy-4h-azet-3-yl]-1-hydroxybutylidene]amino}-3-hydroxybutanoic acid)