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Showing NP-Card for 6-Hydroxynicotinic acid (NP0000362)

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Record Information
Version1.0
Created at2006-05-22 15:12:01 UTC
Updated at2024-04-19 09:50:41 UTC
NP-MRD IDNP0000362
Secondary Accession NumbersNone
Natural Product 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
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000362 (6-Hydroxynicotinic acid)

 
  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
Download

3D MOL for NP0000362 (6-Hydroxynicotinic acid)

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
Download

3D SDF for NP0000362 (6-Hydroxynicotinic acid)

 
  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>
NP0000362

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
Download

3D-SDF for NP0000362 (6-Hydroxynicotinic acid)

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
Download

PDB for NP0000362 (6-Hydroxynicotinic acid)

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 NP0000362 (6-Hydroxynicotinic acid)

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 NP0000362 (6-Hydroxynicotinic acid)

OC(=O)C1=CN=C(O)C=C1
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INCHI for NP0000362 (6-Hydroxynicotinic acid)

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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View in JSmol
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
Chemical FormulaC6H5NO3
Average Mass139.1088 Da
Monoisotopic Mass139.02694 Da
IUPAC Name6-hydroxypyridine-3-carboxylic acid
Traditional Name6-hydroxynicotinic acid
CAS Registry Number5006-66-6
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduNot AvailableNot Available2023-08-11View Spectrum
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduNot AvailableNot Available2023-08-11View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Arabidopsis thalianaKNApSAcK Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mus musculusLOTUS Database
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridinecarboxylic acids and derivatives
Direct ParentPyridinecarboxylic acids
Alternative Parents
Substituents
  • Pyridine carboxylic acid
  • Hydroxypyridine
  • Heteroaromatic compound
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point310 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility13.7 g/LALOGPS
logP0.71ALOGPS
logP0.7ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)3.77ChemAxon
pKa (Strongest Basic)0.51ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70.42 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity33.45 m³·mol⁻¹ChemAxon
Polarizability12.31 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002658
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023041
KNApSAcK IDC00007415
Chemspider ID65756
KEGG Compound IDC01020
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound72924
PDB IDNot Available
ChEBI ID16168
Good Scents IDNot Available
References
General References
  1. Gupta A, Dwivedi M, Nagana Gowda GA, Ayyagari A, Mahdi AA, Bhandari M, Khetrapal CL: (1)H NMR spectroscopy in the diagnosis of Pseudomonas aeruginosa-induced urinary tract infection. NMR Biomed. 2005 Aug;18(5):293-9. [PubMed:15759292 ]
  2. Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C: Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Anal Chem. 2012 Aug 7;84(15):6429-37. doi: 10.1021/ac300829f. Epub 2012 Jul 17. [PubMed:22770225 ]
  3. Shiraishi S, Sakamoto N, Maeda K, Ohki T, Hosoi M, Ohta K, Yamanaka N: Availability of 6-hydroxynicotinic acid for rapid identification of Pseudomonas aeruginosa and Serratia marcescens. J Chromatogr. 1985 Feb 27;338(1):51-9. [PubMed:3926801 ]
  4. Hu X, Xia Y, Liu Y, Zhao F, Zeng B: Determination of patulin using dual-dummy templates imprinted electrochemical sensor with PtPd decorated N-doped porous carbon for amplification. Mikrochim Acta. 2021 Apr 2;188(5):148. doi: 10.1007/s00604-021-04812-2. [PubMed:33797604 ]
  5. Li SS, Niu M, Jing J, Huang Y, Zhang ZT, Chen SS, Shi GZ, He X, Zhang HZ, Xiao XH, Zou ZS, Yu YC, Wang JB: Metabolomic Signatures of Autoimmune Hepatitis in the Development of Cirrhosis. Front Med (Lausanne). 2021 Mar 12;8:644376. doi: 10.3389/fmed.2021.644376. eCollection 2021. [PubMed:33777984 ]
  6. Booth WT, Davis RR, Deora R, Hollis T: Structural mechanism for regulation of DNA binding of BpsR, a Bordetella regulator of biofilm formation, by 6-hydroxynicotinic acid. PLoS One. 2019 Nov 7;14(11):e0223387. doi: 10.1371/journal.pone.0223387. eCollection 2019. [PubMed:31697703 ]
  7. Liu X, Zhao K, Yang X, Zhao Y: Gut Microbiota and Metabolome Response of Decaisnea insignis Seed Oil on Metabolism Disorder Induced by Excess Alcohol Consumption. J Agric Food Chem. 2019 Sep 25;67(38):10667-10677. doi: 10.1021/acs.jafc.9b04792. Epub 2019 Sep 16. [PubMed:31483636 ]
  8. Zhao M, Shao H, He Y, Li H, Yan M, Jiang Z, Wang J, Abd El-Aty AM, Hacimuftuoglu A, Yan F, Wang Y, She Y: The determination of patulin from food samples using dual-dummy molecularly imprinted solid-phase extraction coupled with LC-MS/MS. J Chromatogr B Analyt Technol Biomed Life Sci. 2019 Sep 1;1125:121714. doi: 10.1016/j.jchromb.2019.121714. Epub 2019 Jul 18. [PubMed:31357106 ]
  9. Sun G, Zhang M, Liu X, Gao Q, Jiang W, Zhou Y, Wang H, Cui M, Qiu J, Xu J, Hong Q: Isolation and Characterization of the Pymetrozine-Degrading Strain Pseudomonas sp. BYT-1. J Agric Food Chem. 2019 Apr 17;67(15):4170-4176. doi: 10.1021/acs.jafc.8b06155. Epub 2019 Apr 2. [PubMed:30912660 ]