6-Hydroxynicotinic acid (CHEM020749)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 07:23:26 UTC
Update Date2016-11-09 01:16:15 UTC
Accession NumberCHEM020749
Identification
Common Name6-Hydroxynicotinic acid
ClassSmall Molecule
DescriptionA monohydroxypyridine that is the 6-hydroxy derivative of nicotinic acid.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass139.109 g/mol
Monoisotopic Mass139.027 g/mol
CAS Registry Number5006-66-6
IUPAC Name6-hydroxypyridine-3-carboxylic acid
Traditional Name6-hydroxynicotinic acid
SMILESOC(=O)C1=CN=C(O)C=C1
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014i-1690000000-133fa3cce9e59e8b53a9Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-014i-2790000000-e603f3ef71d861b6c58fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-0290000000-8fed092a7657e583c5d7Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-1690000000-133fa3cce9e59e8b53a9Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-2790000000-e603f3ef71d861b6c58fSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-2790000000-3e2e99cadebe36280a89Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-007a-8900000000-ec493835a384bb643581Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-02mi-9760000000-b9c1d6de28d6f1526e6fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-1900000000-c2874566b889f07322c6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000f-9800000000-79d5e1067ef5dc7a1ac8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000f-9800000000-64f4c9b54adbcf50e4f2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9400000000-c052843ee5e55f4051a9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-4e7b7d18474bf24300d6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0fb9-9400000000-bca0e5c9a959c7a9be6cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-056r-9300000000-03e6711f1fe2eb0fba23Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0a4i-9100000000-e0803e84466b5985c3b2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a4i-9000000000-b9b83bf3dff7e6c924faSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0006-9000000000-0191434ea4b20d4f055bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0006-1900000000-349f5be72008a76679c5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0096-9600000000-1b3d37aa49ae31d7e29cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0006-9100000000-a528aab22cb1f9af4380Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-1900000000-c2874566b889f07322c6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000f-9800000000-deb0d54a79b61d71a9fcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000f-9800000000-64f4c9b54adbcf50e4f2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9400000000-c052843ee5e55f4051a9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-4e7b7d18474bf24300d6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0006-9100000000-a528aab22cb1f9af4380Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0900000000-c48a238051ddd4bb8409Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-2900000000-4808d9beefef60fc7a30Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02fx-9100000000-067bfb3f0aa479a4996cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000l-5900000000-2065745b7d041addf9b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9400000000-9a8d921204197689240aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-618a7376f25ea052e158Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002658
FooDB IDFDB023041
Phenol Explorer IDNot Available
KNApSAcK IDC00007415
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID65756
ChEBI ID16168
PubChem Compound ID72924
Kegg Compound IDC01020
YMDB IDNot Available
ECMDB IDECMDB23803
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=13463004
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=14389240
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15759292
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=18338586
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21389975
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22770225
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=30810301
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=31697703
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=3926801
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=5079068
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=5128334
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=5128335
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=5498533
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=5767303
15. Boyer, J. H.; Schoen, W. 6-Hydroxynicotinic acid. Organic Syntheses (1956), 36 44-6.
16. Boyer, J. H.; Schoen, W. 6-Hydroxynicotinic acid. Organic Syntheses (1956), 36 44-6.
17. 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.
18. 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.