Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2022-03-07 02:49:10 UTC |
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HMDB ID | HMDB0001488 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Nicotinic acid |
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Description | Nicotinic acid, also known as niacin or vitamin B3, is a water-soluble vitamin whose derivatives such as NADH, NAD, NAD+, and NADP play essential roles in energy metabolism in the living cell and DNA repair. The designation vitamin B3 also includes the amide form, nicotinamide or niacinamide. Severe lack of niacin causes the deficiency disease pellagra, whereas a mild deficiency slows down the metabolism decreasing cold tolerance. The recommended daily allowance of niacin is 2-12 mg a day for children, 14 mg a day for women, 16 mg a day for men, and 18 mg a day for pregnant or breast-feeding women. It is found in various animal and plant tissues and has pellagra-curative, vasodilating, and antilipemic properties. The liver can synthesize niacin from the essential amino acid tryptophan, but the synthesis is extremely slow and requires vitamin B6; 60 mg of tryptophan are required to make one milligram of niacin. Bacteria in the gut may also perform the conversion but are inefficient. |
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Structure | InChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9) |
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Synonyms | Value | Source |
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3-Carboxypyridine | ChEBI | 3-Pyridinecarboxylic acid | ChEBI | 3-Pyridylcarboxylic acid | ChEBI | Acide nicotinique | ChEBI | Acido nicotinico | ChEBI | Acidum nicotinicum | ChEBI | Anti-pellagra vitamin | ChEBI | beta-Pyridinecarboxylic acid | ChEBI | m-Pyridinecarboxylic acid | ChEBI | Niacin | ChEBI | Nikotinsaeure | ChEBI | P.P. factor | ChEBI | Pellagra preventive factor | ChEBI | PP Factor | ChEBI | Pyridine-beta-carboxylic acid | ChEBI | Vitamin b3 | ChEBI | Niacor | Kegg | Niaspan | Kegg | 3-Pyridinecarboxylate | Generator | 3-Pyridylcarboxylate | Generator | b-Pyridinecarboxylate | Generator | b-Pyridinecarboxylic acid | Generator | beta-Pyridinecarboxylate | Generator | Β-pyridinecarboxylate | Generator | Β-pyridinecarboxylic acid | Generator | m-Pyridinecarboxylate | Generator | Pyridine-b-carboxylate | Generator | Pyridine-b-carboxylic acid | Generator | Pyridine-beta-carboxylate | Generator | Pyridine-β-carboxylate | Generator | Pyridine-β-carboxylic acid | Generator | Nicotinate | Generator | 3-Carboxylpyridine | HMDB | Akotin | HMDB | Apelagrin | HMDB | Daskil | HMDB | Efacin | HMDB | Enduracin | HMDB | Linic | HMDB | Niac | HMDB | Niacine | HMDB | Nicacid | HMDB | Nicamin | HMDB | Nicangin | HMDB | Nico-span | HMDB | Nicobid | HMDB | Nicocap | HMDB | Nicodelmine | HMDB | Nicolar | HMDB | Niconacid | HMDB | Nicosan 3 | HMDB | Nicotinipca | HMDB | Nicyl | HMDB | Nyclin | HMDB | Pellagrin | HMDB | Pelonin | HMDB | Slo-niacin | HMDB | Wampocap | HMDB | Aluminum salt, niacin | HMDB | Induracin | HMDB | Niacin cobalt (2+) salt | HMDB | Niacin iron (2+) salt | HMDB | Niacin lithium salt | HMDB | Niacin magnesium salt | HMDB | Niacin sodium salt | HMDB | Nico-400 | HMDB | Potassium salt, niacin | HMDB | Sodium salt, niacin | HMDB | Tosylate, niacin | HMDB | Nicotinate, lithium | HMDB | Hydrochloride, niacin | HMDB | Niacin aluminum salt | HMDB | Niacin calcium salt | HMDB | Niacin copper (2+) salt | HMDB | Niacin hydrochloride | HMDB | Niacin lithium salt, hemihydrate | HMDB | Nico400 | HMDB | Tartrate, niacin | HMDB | 3 Pyridinecarboxylic acid | HMDB | Lithium nicotinate | HMDB | Niacin ammonium salt | HMDB | Niacin manganese (2+) salt | HMDB | Niacin potassium salt | HMDB | Niacin tartrate | HMDB | Niacin tosylate | HMDB | Niacin zinc salt | HMDB | Nico 400 | HMDB |
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Chemical Formula | C6H5NO2 |
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Average Molecular Weight | 123.1094 |
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Monoisotopic Molecular Weight | 123.032028409 |
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IUPAC Name | pyridine-3-carboxylic acid |
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Traditional Name | niacin |
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CAS Registry Number | 59-67-6 |
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SMILES | OC(=O)C1=CN=CC=C1 |
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InChI Identifier | InChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9) |
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InChI Key | PVNIIMVLHYAWGP-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
- 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 | |
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Disposition | Biological locationRoute of exposureSourceEndogenousExogenousFood- Food (HMDB: HMDB0001488)
Animal originHerb and spiceVegetableFruitNutCereal and cereal productPulseGourdCoffee and coffee productSoyTeaBaking goodDishBeverageAquatic originEggConfectioneryMilk and milk productOther milk productFermented milkFermented milk productUnfermented milk- Milk (Other mammals) (FooDB: FOOD00690)
- Milk (Human) (FooDB: FOOD00666)
- Milk (Cow) (FooDB: FOOD00618)
- Cow milk, pasteurized, vitamin A + D added, 0% fat (FooDB: FOOD00889)
- Cow milk, pasteurized, vitamin A + D added, 1% fat (FooDB: FOOD00890)
- Cow milk, pasteurized, vitamin A + D added, 2% fat (FooDB: FOOD00891)
- Cow milk, pasteurized, vitamin D added, 3.25% fat (FooDB: FOOD00892)
Fat and oilCocoa and cocoa productBaby foodUnclassified food or beverageSnack Synthetic |
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Process | |
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Role | |
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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 | 236.6 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 18 mg/mL | Not Available | LogP | 0.36 | SANGSTER (1993) |
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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 IndicesUnderivatizedDerivatized |
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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 - Nicotinic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS) | splash10-053i-0900000000-5daf0093df6c21c7279f | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Nicotinic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS) | splash10-053i-0900000000-f38b6609b45de8c74565 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Nicotinic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0540-0900000000-4f55c81a6cd42f1b961d | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Nicotinic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS) | splash10-057r-5900000000-00bf3662b5b9db533c0a | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Nicotinic acid GC-MS (1 TMS) | splash10-0569-2900000000-7820ea736b03b71d2cb8 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Nicotinic acid EI-B (Non-derivatized) | splash10-0kmi-7900000000-9e4efda763cce5ddfe57 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Nicotinic acid GC-EI-TOF (Non-derivatized) | splash10-053i-0900000000-5daf0093df6c21c7279f | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Nicotinic acid GC-EI-TOF (Non-derivatized) | splash10-053i-0900000000-f38b6609b45de8c74565 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Nicotinic acid GC-EI-TOF (Non-derivatized) | splash10-0540-0900000000-4f55c81a6cd42f1b961d | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Nicotinic acid GC-EI-TOF (Non-derivatized) | splash10-057r-5900000000-00bf3662b5b9db533c0a | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Nicotinic acid GC-MS (Non-derivatized) | splash10-0569-2900000000-7820ea736b03b71d2cb8 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Nicotinic acid GC-EI-TOF (Non-derivatized) | splash10-0540-0900000000-a701904fe6ded0abd98f | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Nicotinic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-05i0-9700000000-d7620f1dc8f42d1498b9 | 2016-09-22 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Nicotinic acid GC-MS (1 TMS) - 70eV, Positive | splash10-05fr-9600000000-c3303cf4e83870b3e656 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Nicotinic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Nicotinic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0kor-8900000000-7d3f033a49f5fad75f33 | 2014-09-20 | Not Available | 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 - Nicotinic acid Quattro_QQQ 10V, Positive-QTOF (Annotated) | splash10-00di-1900000000-27508608b33f1fb9f221 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nicotinic acid Quattro_QQQ 25V, Positive-QTOF (Annotated) | splash10-003r-9100000000-a2037c9695659dceabd1 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nicotinic acid Quattro_QQQ 40V, Positive-QTOF (Annotated) | splash10-0ufr-9100000000-4a2649a83ad2a40e5194 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nicotinic acid EI-B (HITACHI M-80) , Positive-QTOF | splash10-0kmi-7900000000-1bc47d1b1850f54fb7c2 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nicotinic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF | splash10-00di-1900000000-a352c5ce16d4b682b052 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nicotinic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF | splash10-004i-9000000000-ab23ecb032e387b40bd9 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nicotinic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF | splash10-004i-9000000000-02e37a1cfd3947037579 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nicotinic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF | splash10-004i-9000000000-75d7e6658d2d6eca736e | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nicotinic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF | splash10-0udi-9000000000-21a2d68d4f364c596f1d | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nicotinic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF | splash10-0ab9-0900000000-a74db528f61c435876c8 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nicotinic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF | splash10-00di-6900000000-773c08ab92ace4d48a9c | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nicotinic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF | splash10-00aj-9100000000-07b12fbe942e6c7fb12d | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nicotinic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF | splash10-005a-9000000000-66e0a5ba2ca8dbba1ed5 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nicotinic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOF | splash10-004i-9000000000-fbf8ba47b56d7cc7be81 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nicotinic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF | splash10-00di-0900000000-eaf82f6ab0befde118e9 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nicotinic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive-QTOF | splash10-00di-0900000000-eaf82f6ab0befde118e9 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nicotinic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF | splash10-004i-9300000000-b1a48f694fba565108a1 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nicotinic acid LC-ESI-QQ , negative-QTOF | splash10-00di-1900000000-a352c5ce16d4b682b052 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nicotinic acid LC-ESI-QQ , negative-QTOF | splash10-004i-9000000000-ab23ecb032e387b40bd9 | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nicotinic acid 10V, Positive-QTOF | splash10-00di-0900000000-25068c42378f72756922 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nicotinic acid 20V, Positive-QTOF | splash10-00di-3900000000-6278a1e122005f48fcaf | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nicotinic acid 40V, Positive-QTOF | splash10-0ue9-9000000000-e4e41ed9bef32955889e | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nicotinic acid 10V, Negative-QTOF | splash10-00di-4900000000-85d44ecd8ad348eeacd1 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nicotinic acid 20V, Negative-QTOF | splash10-004i-9300000000-4911305982583ae20895 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nicotinic acid 40V, Negative-QTOF | splash10-004i-9000000000-4dea4a2d4a55907605ea | 2016-09-12 | 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) | 2012-12-04 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
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