| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2006-05-22 09:12:01 -0600 |
| Update Date |
2013-02-08 17:12:02 -0700 |
| HMDB ID |
HMDB02658 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
6-Hydroxynicotinic acid |
| Description |
6-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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- 1,6-Dihydro-6-oxo-3-pyridinecarboxylic acid
- 1,6-Dihydro-6-oxo-Nicotinic acid
- 2-Hydroxy-5-carboxypyridine
- 2-Hydroxypyridine-5-carboxylic acid
- 2-Pyridone-5-carboxylic acid
- 5-Carboxy-2-pyridone
- 6-Hydroxy-Nicotinic acid
- 6-Hydroxyniacin
- 6-Hydroxynicotinate
- 6-Hydroxynicotinic acid
- 6-Hydroxypyridine-3-carboxylic acid
|
| Chemical Formula |
C6H5NO3 |
| Average Molecular Weight |
139.1088 |
| Monoisotopic Molecular Weight |
139.026943031 |
| IUPAC Name |
6-hydroxypyridine-3-carboxylic acid |
| Traditional IUPAC Name |
6-hydroxynicotinic acid |
| CAS Registry Number |
5006-66-6 |
| 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 Key |
BLHCMGRVFXRYRN-UHFFFAOYSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Aromatic Heteromonocyclic Compounds |
| Class |
Pyridines and Derivatives |
| Sub Class |
Pyridinecarboxylic Acids and Derivatives |
| Other Descriptors |
- Pyridine alkaloids(KEGG)
- Pyridines and Derivatives
- monohydroxypyridine(ChEBI)
|
| Substituents |
- Carboxylic Acid
- Pyridinone
|
| Direct Parent |
Pyridinecarboxylic Acids and Derivatives |
| Ontology |
|---|
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
Not Available |
| Application |
Not Available |
| Cellular locations |
Not Available |
| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
310 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
Not Available |
Not Available |
|
| Predicted Properties |
|
| Spectra |
|---|
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| 1H NMR Spectrum |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50 |
| MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies ) |
| MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) |
| MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30 |
| MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) |
| MS/MS Spectrum GC-MS |
| [1H,13C] 2D NMR Spectrum |
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| Biological Properties |
|---|
| Cellular Locations |
Not Available
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| Biofluid Locations |
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| Tissue Location |
Not Available
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| Pathways |
Not Available
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| Normal Concentrations |
|---|
|
| Urine |
Detected and not Quantified |
|
Not Applicable |
Adult (>18 years old) |
Both |
Normal |
Not Available |
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| Abnormal Concentrations |
|---|
|
| Urine |
Detected and Quantified |
|
0.5 (0.0-1.0) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Prostate Cancer |
Estimated concentration
|
| Urine |
Detected and not Quantified |
|
Not Applicable |
Adult (>18 years old) |
Both |
Autosomal dominant polycystic kidney disease |
Not Available |
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| Associated Disorders and Diseases |
|---|
| Disease References |
| Prostate cancer |
|---|
- 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.
Pubmed: 19212411
|
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| Associated OMIM IDs |
|
| External Links |
|---|
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB023041 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
65756 |
| KEGG Compound ID |
C01020 |
| BioCyc ID |
Not Available |
| BiGG ID |
Not Available |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB02658 |
| Metagene Link |
HMDB02658 |
| METLIN ID |
Not Available |
| PubChem Compound |
72924 |
| PDB ID |
Not Available |
| ChEBI ID |
16168 |
| References |
|---|
| Synthesis Reference |
Boyer, J. H.; Schoen, W. 6-Hydroxynicotinic acid. Organic Syntheses (1956), 36 44-6. |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- 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
|
