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Record Information
Version3.6
Creation Date2006-05-22 15:12:01 UTC
Update Date2016-02-11 01:05:44 UTC
HMDB IDHMDB02658
Secondary Accession NumbersNone
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 ).
Structure
Thumb
Synonyms
ValueSource
6-HydroxynicotinateChEBI
6-Hydroxynicotinic acidGenerator
6-oxo-1H-Pyridine-3-carboxylateGenerator
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
Chemical FormulaC6H5NO3
Average Molecular Weight139.1088
Monoisotopic Molecular Weight139.026943031
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 KeyInChIKey=BLHCMGRVFXRYRN-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pyridinecarboxylic acids. These 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity33.45 m3·mol-1ChemAxon
Polarizability12.31 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-014i-1690000000-133fa3cce9e59e8b53a9View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-014i-2790000000-e603f3ef71d861b6c58fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-1900000000-c2874566b889f07322c6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000f-9800000000-79d5e1067ef5dc7a1ac8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000f-9800000000-64f4c9b54adbcf50e4f2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9400000000-c052843ee5e55f4051a9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-4e7b7d18474bf24300d6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0fb9-9400000000-bca0e5c9a959c7a9be6cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-056r-9300000000-03e6711f1fe2eb0fba23View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0a4i-9100000000-e0803e84466b5985c3b2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a4i-9000000000-b9b83bf3dff7e6c924faView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0006-9000000000-0191434ea4b20d4f055bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0006-1900000000-349f5be72008a76679c5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0096-9600000000-1b3d37aa49ae31d7e29cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0006-9100000000-a528aab22cb1f9af4380View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.5 (0.0-1.0) umol/mmol creatinineAdult (>18 years old)Both
Prostate Cancer
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothAutosomal dominant polycystic kidney disease (ADPKD) details
Associated Disorders and Diseases
Disease References
Prostate cancer
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. [19212411 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023041
KNApSAcK IDNot Available
Chemspider ID65756
KEGG Compound IDC01020
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02658
Metagene LinkHMDB02658
METLIN IDNot Available
PubChem Compound72924
PDB IDNot Available
ChEBI ID16168
References
Synthesis ReferenceBoyer, J. H.; Schoen, W. 6-Hydroxynicotinic acid. Organic Syntheses (1956), 36 44-6.
Material Safety Data Sheet (MSDS)Download (PDF)
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. [15759292 ]
  2. 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. [3926801 ]