Showing metabocard for Pyridine-2,6-dithiocarboxylic acid (MMDBc0005596)

Record Information
Version2.0
StatusDetected and Quantified
Creation Date2021-05-14 23:08:12 UTC
Update Date2025-10-07 16:05:03 UTC
Metabolite IDMMDBc0005596
Metabolite Identification
Common NamePyridine-2,6-dithiocarboxylic acid
DescriptionPyridine-2,6-dithiocarboxylic acid is a bacterial metabolite classified as a metal chelator. It is produced by various Pseudomonas species, including Pseudomonas stutzeri and Pseudomonas putida, and has garnered attention for its potential applications in both environmental and biomedical contexts. Notably, pyridine-2,6-dithiocarboxylic acid has been identified as a novel inhibitor of New Delhi Metallo β-Lactamase-1, highlighting its significance in combating antibiotic resistance (PMID:32498259 ). Additionally, it has been shown to modulate inflammatory responses by reducing TNF-α expression when used in conjunction with MyD88 siRNA or NF-κB inhibitors (PMID:21691078 ). The compound is also implicated in the production of siderophores, as its synthesis is coordinated with that of pyoverdine, suggesting a role in iron acquisition for bacteria (PMID:14756880 ). Furthermore, pyridine-2,6-dithiocarboxylic acid has demonstrated effectiveness in promoting the dechlorination of carbon tetrachloride, a toxic environmental pollutant (PMID:14756880 ). Overall, its multifaceted roles in microbial physiology and potential therapeutic applications underscore its importance in both chemistry and biology.
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007f2e2dbace00>


  Mrv1533004181500362D          

 12 12  0  0  0  0            999 V2000
    1.4289    2.4750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f2e2dbace00>

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3D SDF for #<Metabolite:0x00007f2e2dbace00>

  Mrv1533004181500362D          

 12 12  0  0  0  0            999 V2000
    1.4289    2.4750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0005596

> <DATABASE_NAME>
MIME

> <SMILES>
SC(=O)C1=CC=CC(=N1)C(S)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H5NO2S2/c9-6(11)4-2-1-3-5(8-4)7(10)12/h1-3H,(H,9,11)(H,10,12)

> <INCHI_KEY>
SSRIAMRLMUFTNV-UHFFFAOYSA-N

> <FORMULA>
C7H5NO2S2

> <MOLECULAR_WEIGHT>
199.24

> <EXACT_MASS>
198.976170753

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
18.493816438456705

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
pyridine-2,6-dicarbothioic diS-acid

> <ALOGPS_LOGP>
2.02

> <JCHEM_LOGP>
-2.333382060461938

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
-4.683767775254078

> <JCHEM_PKA_STRONGEST_ACIDIC>
-5.483862381404795

> <JCHEM_PKA_STRONGEST_BASIC>
10.38455036242995

> <JCHEM_POLAR_SURFACE_AREA>
47.03

> <JCHEM_REFRACTIVITY>
50.4971

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.57e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,6-pyridinedicarbothioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007f2e2dbace00>
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PDB for #<Metabolite:0x00007f2e2dbace00>
HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  S   UNK     0       2.667   4.620   0.000  0.00  0.00           S+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   12  S   UNK     0      -2.667   0.000   0.000  0.00  0.00           S+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8    4                                                       
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for #<Metabolite:0x00007f2e2dbace00>
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SMILES for #<Metabolite:0x00007f2e2dbace00>
SC(=O)C1=CC=CC(=N1)C(S)=O
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INCHI for #<Metabolite:0x00007f2e2dbace00>
InChI=1S/C7H5NO2S2/c9-6(11)4-2-1-3-5(8-4)7(10)12/h1-3H,(H,9,11)(H,10,12)
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Synonyms
ValueSource
6-(Sulphanylcarbonyl)pyridine-2-carbothioic O-acidGenerator
2,6-PYRIDINEDICARBOTHIOateGenerator
Pyridine-2,6-bis(thiocarboxylate)MeSH
Pyridine-2,6-bis(thiocarboxylic acid)MeSH
Molecular FormulaC7H5NO2S2
Average Mass199.24
Monoisotopic Mass198.976170753
IUPAC Namepyridine-2,6-dicarbothioic diS-acid
Traditional Name2,6-pyridinedicarbothioic acid
CAS Registry NumberNot Available
SMILES
SC(=O)C1=CC=CC(=N1)C(S)=O
InChI Identifier
InChI=1S/C7H5NO2S2/c9-6(11)4-2-1-3-5(8-4)7(10)12/h1-3H,(H,9,11)(H,10,12)
InChI KeySSRIAMRLMUFTNV-UHFFFAOYSA-N