Showing metabocard for 6-Hydroxynicotinic acid (MMDBc0000594)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:50:42 UTC
Update Date2024-10-17 18:02:56 UTC
Metabolite IDMMDBc0000594
Metabolite Identification
Common Name6-Hydroxynicotinic acid
Description6-Hydroxynicotinic acid (6-OHNA) is exploited in the use of NMR spectroscopy or gas chromatography--mass spectrometry for the diagnosis of Pseudomonas aeruginosa in urinary tract infection. Among the common bacteria causing urinary infection, only P. aeruginosa produces 6-hydroxynicotinic acid from nicotinic acid. Pseudomonas aeruginosa infection has been reported to be the third leading cause of urinary infection, accounting for 11% of such infections, the first and second being Escherichia coli and Klebsiella pneumonia, respectively. Analyses of the NMR spectra of the bacterial media with variable cell count of P. aeruginosa, shows that the intensity of the signals of the 6-hydroxynicotinic acid increases with increasing number of bacterial cells (PMID:3926801 , 15759292 ). 6-hydroxynicotinic acid can also be found in Achromobacter and Serratia.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x0000556b667773e8>

 
  Mrv1652305271900012D          
 
 10 10  0  0  0  0            999 V2000
   13.3034   -9.4659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9711   -9.8336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5909   -9.8821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3034   -8.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9711  -10.6884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6761   -9.4212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8822   -9.4659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5909   -8.2360    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8822   -8.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1772   -8.2360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  2  0  0  0  0
  4  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8  9  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x0000556b667773e8>

HMDB0002658
     RDKit          3D
6-Hydroxynicotinic acid
 15 15  0  0  0  0  0  0  0  0999 V2000
   -2.7012   -1.4950   -0.0957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1873   -0.3947    0.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9795    0.6052    0.7068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7298   -0.2242    0.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1174    0.9646    0.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2466    1.0388    0.1621 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0062    0.0121   -0.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3832    0.1282   -0.5201 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3624   -1.1414   -0.6422 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0397   -1.2541   -0.4634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8683    0.8494    0.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7025    1.7969    0.7583 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7405    1.9620    0.4126 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9357   -0.6557   -0.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4284   -2.1921   -0.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10  4  1  0
  3 11  1  0
  5 12  1  0
  6 13  1  0
  8 14  1  0
 10 15  1  0
M  END
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3D SDF for #<Metabolite:0x0000556b667773e8>

 
  Mrv1652305271900012D          
 
 10 10  0  0  0  0            999 V2000
   13.3034   -9.4659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9711   -9.8336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5909   -9.8821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3034   -8.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9711  -10.6884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6761   -9.4212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8822   -9.4659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5909   -8.2360    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8822   -8.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1772   -8.2360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  2  0  0  0  0
  4  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8  9  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000594

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)C1=CN=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C6H5NO3/c8-5-2-1-4(3-7-5)6(9)10/h1-3H,(H,7,8)(H,9,10)

> <INCHI_KEY>
BLHCMGRVFXRYRN-UHFFFAOYSA-N

> <FORMULA>
C6H5NO3

> <MOLECULAR_WEIGHT>
139.1088

> <EXACT_MASS>
139.026943031

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
12.306860954062515

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-hydroxypyridine-3-carboxylic acid

> <ALOGPS_LOGP>
0.71

> <JCHEM_LOGP>
0.7040485053333334

> <ALOGPS_LOGS>
-1.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.482138442250873

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.771326866380843

> <JCHEM_PKA_STRONGEST_BASIC>
0.5079910491749348

> <JCHEM_POLAR_SURFACE_AREA>
70.42

> <JCHEM_REFRACTIVITY>
33.4517

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.37e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxynicotinic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x0000556b667773e8>

HMDB0002658
     RDKit          3D
6-Hydroxynicotinic acid
 15 15  0  0  0  0  0  0  0  0999 V2000
   -2.7012   -1.4950   -0.0957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1873   -0.3947    0.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9795    0.6052    0.7068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7298   -0.2242    0.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1174    0.9646    0.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2466    1.0388    0.1621 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0062    0.0121   -0.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3832    0.1282   -0.5201 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3624   -1.1414   -0.6422 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0397   -1.2541   -0.4634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8683    0.8494    0.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7025    1.7969    0.7583 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7405    1.9620    0.4126 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9357   -0.6557   -0.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4284   -2.1921   -0.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10  4  1  0
  3 11  1  0
  5 12  1  0
  6 13  1  0
  8 14  1  0
 10 15  1  0
M  END
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PDB for #<Metabolite:0x0000556b667773e8>

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      24.833 -17.670   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      26.079 -18.356   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.503 -18.447   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.833 -16.130   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      26.079 -19.952   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      27.395 -17.586   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      22.180 -17.670   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      23.503 -15.374   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      22.180 -16.130   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      20.864 -15.374   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2                                                            
CONECT    6    2                                                            
CONECT    7    3    9                                                       
CONECT    8    4    9                                                       
CONECT    9    7   10    8                                                  
CONECT   10    9                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for #<Metabolite:0x0000556b667773e8>

COMPND    HMDB0002658
HETATM    1  O1  UNL     1      -2.701  -1.495  -0.096  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.187  -0.395   0.215  1.00  0.00           C  
HETATM    3  O2  UNL     1      -2.979   0.605   0.707  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.730  -0.224   0.035  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.117   0.965   0.362  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.247   1.039   0.162  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.006   0.012  -0.334  1.00  0.00           C  
HETATM    8  O3  UNL     1       3.383   0.128  -0.520  1.00  0.00           O  
HETATM    9  N1  UNL     1       1.362  -1.141  -0.642  1.00  0.00           N  
HETATM   10  C6  UNL     1       0.040  -1.254  -0.463  1.00  0.00           C  
HETATM   11  H1  UNL     1      -3.868   0.849   0.275  1.00  0.00           H  
HETATM   12  H2  UNL     1      -0.702   1.797   0.758  1.00  0.00           H  
HETATM   13  H3  UNL     1       1.740   1.962   0.413  1.00  0.00           H  
HETATM   14  H4  UNL     1       3.936  -0.656  -0.148  1.00  0.00           H  
HETATM   15  H5  UNL     1      -0.428  -2.192  -0.724  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   11
CONECT    4    5    5   10
CONECT    5    6   12
CONECT    6    7    7   13
CONECT    7    8    9
CONECT    8   14
CONECT    9   10   10
CONECT   10   15
END
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SMILES for #<Metabolite:0x0000556b667773e8>

OC(=O)C1=CN=C(O)C=C1
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INCHI for #<Metabolite:0x0000556b667773e8>

InChI=1S/C6H5NO3/c8-5-2-1-4(3-7-5)6(9)10/h1-3H,(H,7,8)(H,9,10)
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Synonyms
ValueSource
6-HydroxynicotinateChEBI
1,6-dihydro-6-oxo-3-Pyridinecarboxylic acidHMDB
1,6-dihydro-6-oxo-Nicotinic acidHMDB
2-Hydroxy-5-carboxypyridineHMDB
2-Hydroxypyridine-5-carboxylic acidHMDB
2-Pyridone-5-carboxylic acidHMDB
5-Carboxy-2-pyridoneHMDB
6-Hydroxy-nicotinic acidHMDB
6-HydroxyniacinHMDB
6-Hydroxypyridine-3-carboxylic acidHMDB
6-Hydroxynicotinic acidKEGG
Molecular FormulaC6H5NO3
Average Mass139.1088
Monoisotopic Mass139.026943031
IUPAC Name6-hydroxypyridine-3-carboxylic acid
Traditional Name6-hydroxynicotinic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C1=CN=C(O)C=C1
InChI Identifier
InChI=1S/C6H5NO3/c8-5-2-1-4(3-7-5)6(9)10/h1-3H,(H,7,8)(H,9,10)
InChI KeyBLHCMGRVFXRYRN-UHFFFAOYSA-N