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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:01 UTC
Update Date2021-09-07 16:45:33 UTC
HMDB IDHMDB0002658
Secondary Accession Numbers
  • HMDB02658
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
Data?1582752253
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 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 KeyBLHCMGRVFXRYRN-UHFFFAOYSA-N
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
Ontology
Disposition

Biological location:

Source:

Process

Naturally occurring process:

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
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014i-1690000000-133fa3cce9e59e8b53a92014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-014i-2790000000-e603f3ef71d861b6c58f2014-06-16View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-0290000000-8fed092a7657e583c5d72017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-1690000000-133fa3cce9e59e8b53a92017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-2790000000-e603f3ef71d861b6c58f2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-2790000000-3e2e99cadebe36280a892017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-007a-8900000000-ec493835a384bb6435812017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-02mi-9760000000-b9c1d6de28d6f1526e6f2017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-007a-8900000000-ec493835a384bb6435812021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-1900000000-c2874566b889f07322c62012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000f-9800000000-79d5e1067ef5dc7a1ac82012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000f-9800000000-64f4c9b54adbcf50e4f22012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9400000000-c052843ee5e55f4051a92012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-4e7b7d18474bf24300d62012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0006-9100000000-a528aab22cb1f9af43802012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-1900000000-c2874566b889f07322c62017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000f-9800000000-deb0d54a79b61d71a9fc2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000f-9800000000-64f4c9b54adbcf50e4f22017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9400000000-c052843ee5e55f4051a92017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-4e7b7d18474bf24300d62017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0006-9100000000-a528aab22cb1f9af43802017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0006-9000000000-1d37eb18ba02442145542017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0fb9-9400000000-bca0e5c9a959c7a9be6c2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-056r-9300000000-03e6711f1fe2eb0fba232012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0a4i-9100000000-e0803e84466b5985c3b22012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a4i-9000000000-b9b83bf3dff7e6c924fa2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0006-9000000000-0191434ea4b20d4f055b2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0006-1900000000-349f5be72008a76679c52012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0096-9600000000-1b3d37aa49ae31d7e29c2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0fb9-9400000000-f3f7cac93e02959bf6342017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-056r-9300000000-83afe01d9035d8d824a52017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9100000000-e0803e84466b5985c3b22017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9000000000-b9b83bf3dff7e6c924fa2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-0191434ea4b20d4f055b2017-09-14View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-05View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, predicted)2012-12-05View Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified0.5 (0.0-1.0) umol/mmol creatinineAdult (>18 years old)Both
Prostate Cancer
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAutosomal dominant polycystic kidney disease (ADPKD) details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Diabetes mellitus
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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. doi: 10.1038/nature07762. [PubMed:19212411 ]
Autosomal dominant polycystic kidney disease
  1. Gronwald W, Klein MS, Zeltner R, Schulze BD, Reinhold SW, Deutschmann M, Immervoll AK, Boger CA, Banas B, Eckardt KU, Oefner PJ: Detection of autosomal dominant polycystic kidney disease by NMR spectroscopic fingerprinting of urine. Kidney Int. 2011 Jun;79(11):1244-53. doi: 10.1038/ki.2011.30. Epub 2011 Mar 9. [PubMed:21389975 ]
Diabetes mellitus type 2
  1. Llorach R, Urpi-Sarda M, Tulipani S, Garcia-Aloy M, Monagas M, Andres-Lacueva C: Metabolomic fingerprint in patients at high risk of cardiovascular disease by cocoa intervention. Mol Nutr Food Res. 2013 Jun;57(6):962-73. doi: 10.1002/mnfr.201200736. Epub 2013 May 2. [PubMed:23637065 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
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. [PubMed: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. [PubMed:3926801 ]