Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-05-22 15:12:01 UTC |
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Update Date | 2023-02-21 17:16:27 UTC |
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HMDB ID | HMDB0002658 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 6-Hydroxynicotinic acid |
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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 ). 6-hydroxynicotinic acid can also be found in Achromobacter and Serratia. |
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Structure | 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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Synonyms | Value | Source |
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6-Hydroxynicotinate | ChEBI | 1,6-dihydro-6-oxo-3-Pyridinecarboxylic acid | HMDB | 1,6-dihydro-6-oxo-Nicotinic acid | HMDB | 2-Hydroxy-5-carboxypyridine | HMDB | 2-Hydroxypyridine-5-carboxylic acid | HMDB | 2-Pyridone-5-carboxylic acid | HMDB | 5-Carboxy-2-pyridone | HMDB | 6-Hydroxy-nicotinic acid | HMDB | 6-Hydroxyniacin | HMDB | 6-Hydroxypyridine-3-carboxylic acid | HMDB | 6-Hydroxynicotinic acid | KEGG |
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Chemical Formula | C6H5NO3 |
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Average Molecular Weight | 139.1088 |
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Monoisotopic Molecular Weight | 139.026943031 |
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IUPAC Name | 6-hydroxypyridine-3-carboxylic acid |
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Traditional Name | 6-hydroxynicotinic acid |
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CAS Registry Number | 5006-66-6 |
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SMILES | OC(=O)C1=CN=C(O)C=C1 |
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InChI Identifier | 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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InChI Key | BLHCMGRVFXRYRN-UHFFFAOYSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Pyridines and derivatives |
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Sub Class | Pyridinecarboxylic acids and derivatives |
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Direct Parent | Pyridinecarboxylic acids |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 310 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Experimental Collision Cross Sections |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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6-Hydroxynicotinic acid,1TMS,isomer #1 | C[Si](C)(C)OC(=O)C1=CC=C(O)N=C1 | 1636.8 | Semi standard non polar | 33892256 | 6-Hydroxynicotinic acid,1TMS,isomer #2 | C[Si](C)(C)OC1=CC=C(C(=O)O)C=N1 | 1639.0 | Semi standard non polar | 33892256 | 6-Hydroxynicotinic acid,2TMS,isomer #1 | C[Si](C)(C)OC(=O)C1=CC=C(O[Si](C)(C)C)N=C1 | 1581.3 | Semi standard non polar | 33892256 | 6-Hydroxynicotinic acid,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(O)N=C1 | 1890.9 | Semi standard non polar | 33892256 | 6-Hydroxynicotinic acid,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC=C(C(=O)O)C=N1 | 1876.6 | Semi standard non polar | 33892256 | 6-Hydroxynicotinic acid,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)N=C1 | 2078.9 | Semi standard non polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - 6-Hydroxynicotinic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-014i-1690000000-133fa3cce9e59e8b53a9 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 6-Hydroxynicotinic acid GC-MS (2 TMS) | splash10-014i-2790000000-e603f3ef71d861b6c58f | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 6-Hydroxynicotinic acid EI-B (Non-derivatized) | splash10-014i-0290000000-8fed092a7657e583c5d7 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 6-Hydroxynicotinic acid GC-EI-TOF (Non-derivatized) | splash10-014i-1690000000-133fa3cce9e59e8b53a9 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 6-Hydroxynicotinic acid GC-MS (Non-derivatized) | splash10-014i-2790000000-e603f3ef71d861b6c58f | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 6-Hydroxynicotinic acid GC-EI-TOF (Non-derivatized) | splash10-014i-2790000000-3e2e99cadebe36280a89 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 6-Hydroxynicotinic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-007a-8900000000-ec493835a384bb643581 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 6-Hydroxynicotinic acid GC-MS (2 TMS) - 70eV, Positive | splash10-02mi-9760000000-b9c1d6de28d6f1526e6f | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 6-Hydroxynicotinic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - 6-Hydroxynicotinic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF | splash10-000i-1900000000-c2874566b889f07322c6 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 6-Hydroxynicotinic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF | splash10-000f-9800000000-79d5e1067ef5dc7a1ac8 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 6-Hydroxynicotinic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF | splash10-000f-9800000000-64f4c9b54adbcf50e4f2 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 6-Hydroxynicotinic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF | splash10-0006-9400000000-c052843ee5e55f4051a9 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 6-Hydroxynicotinic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF | splash10-0006-9000000000-4e7b7d18474bf24300d6 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 6-Hydroxynicotinic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF | splash10-0fb9-9400000000-bca0e5c9a959c7a9be6c | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 6-Hydroxynicotinic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF | splash10-056r-9300000000-03e6711f1fe2eb0fba23 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 6-Hydroxynicotinic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF | splash10-0a4i-9100000000-e0803e84466b5985c3b2 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 6-Hydroxynicotinic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF | splash10-0a4i-9000000000-b9b83bf3dff7e6c924fa | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 6-Hydroxynicotinic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOF | splash10-0006-9000000000-0191434ea4b20d4f055b | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 6-Hydroxynicotinic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF | splash10-0006-1900000000-349f5be72008a76679c5 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 6-Hydroxynicotinic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive-QTOF | splash10-0096-9600000000-1b3d37aa49ae31d7e29c | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 6-Hydroxynicotinic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF | splash10-0006-9100000000-a528aab22cb1f9af4380 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 6-Hydroxynicotinic acid LC-ESI-QQ , negative-QTOF | splash10-000i-1900000000-c2874566b889f07322c6 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 6-Hydroxynicotinic acid LC-ESI-QQ , negative-QTOF | splash10-000f-9800000000-deb0d54a79b61d71a9fc | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 6-Hydroxynicotinic acid LC-ESI-QQ , negative-QTOF | splash10-000f-9800000000-64f4c9b54adbcf50e4f2 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 6-Hydroxynicotinic acid LC-ESI-QQ , negative-QTOF | splash10-0006-9400000000-c052843ee5e55f4051a9 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 6-Hydroxynicotinic acid LC-ESI-QQ , negative-QTOF | splash10-0006-9000000000-4e7b7d18474bf24300d6 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 6-Hydroxynicotinic acid LC-ESI-QTOF , negative-QTOF | splash10-0006-9100000000-a528aab22cb1f9af4380 | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Hydroxynicotinic acid 10V, Positive-QTOF | splash10-006x-0900000000-c48a238051ddd4bb8409 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Hydroxynicotinic acid 20V, Positive-QTOF | splash10-00dl-2900000000-4808d9beefef60fc7a30 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Hydroxynicotinic acid 40V, Positive-QTOF | splash10-02fx-9100000000-067bfb3f0aa479a4996c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Hydroxynicotinic acid 10V, Negative-QTOF | splash10-000l-5900000000-2065745b7d041addf9b2 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Hydroxynicotinic acid 20V, Negative-QTOF | splash10-0006-9400000000-9a8d921204197689240a | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Hydroxynicotinic acid 40V, Negative-QTOF | splash10-0006-9000000000-618a7376f25ea052e158 | 2017-09-01 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Experimental 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | 2012-12-05 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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Disease References | Colorectal cancer |
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- 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 ]
- 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 ]
- 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 |
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- 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 |
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- 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 |
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- 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 ]
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