Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:04:48 UTC |
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Update date | 2020-09-17 15:38:56 UTC |
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Primary ID | FDB001014 |
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Secondary Accession Numbers | |
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Chemical Information |
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FooDB Name | Nicotinic acid |
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Description | Nicotinic acid, also known as niacin or 3-carboxypyridine, belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group. A pyridinemonocarboxylic acid that is pyridine in which the hydrogen at position 3 is replaced by a carboxy group. Nicotinic acid is a strong basic compound (based on its pKa). Nicotinic acid exists in all living species, ranging from bacteria to humans. nicotinic acid and ribose 1-phosphate can be biosynthesized from nicotinate D-ribonucleoside through its interaction with the enzyme purine nucleoside phosphorylase. In humans, nicotinic acid is involved in nicotinate and nicotinamide metabolism. Outside of the human body, Nicotinic acid is found, on average, in the highest concentration within a few different foods, such as beers, leavening agents, and yellowfin tuna and in a lower concentration in greater sturgeons, groundcherries, and muskmelons. Nicotinic acid has also been detected, but not quantified in, several different foods, such as chinese bayberries, pineappple sages, green vegetables, brassicas, and cupuaçus. This could make nicotinic acid a potential biomarker for the consumption of these foods. Nicotinic acid is a potentially toxic compound. |
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CAS Number | 59-67-6 |
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Structure | |
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Synonyms | Synonym | 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 | Niacin, USAN | db_source | Niacor (TN) | biospider | Niaspan (TN) | biospider | Nicagin | biospider | Nico-Span | biospider | Nicotinic acid, INN | db_source | Pyridine-β-carboxylic acid | biospider | Pyridine-3-carbonic acid | biospider | Pyridine-3-carboxylic acid | biospider | Pyridinecarboxylic acid, 3- | biospider | Vitamin B3 (Niacin) | manual | Vitamin PP (Niacin) | manual | β-pyridinecarboxylate | Generator | β-pyridinecarboxylic acid | Generator |
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Predicted Properties | |
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Chemical Formula | C6H5NO2 |
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IUPAC name | pyridine-3-carboxylic acid |
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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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Isomeric SMILES | OC(=O)C1=CN=CC=C1 |
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Average Molecular Weight | 123.1094 |
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Monoisotopic Molecular Weight | 123.032028409 |
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Classification |
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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 | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 58.54%; H 4.09%; N 11.38%; O 25.99% | DFC |
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Melting Point | Mp 236° (225-227°) | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | 18 mg/mL at 20 oC | YALKOWSKY,SH & HE,Y (2003) |
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Experimental logP | 0.36 | SANGSTER (1993) |
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Experimental pKa | pKa2 4.82 (25°) | DFC |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-0kor-8900000000-7d3f033a49f5fad75f33 | 2014-09-20 | View Spectrum | GC-MS | Nicotinic acid, 1 TMS, GC-MS Spectrum | splash10-053i-0900000000-5daf0093df6c21c7279f | Spectrum | GC-MS | Nicotinic acid, 1 TMS, GC-MS Spectrum | splash10-053i-0900000000-f38b6609b45de8c74565 | Spectrum | GC-MS | Nicotinic acid, non-derivatized, GC-MS Spectrum | splash10-0540-0900000000-4f55c81a6cd42f1b961d | Spectrum | GC-MS | Nicotinic acid, 1 TMS, GC-MS Spectrum | splash10-057r-5900000000-00bf3662b5b9db533c0a | Spectrum | GC-MS | Nicotinic acid, 1 TMS, GC-MS Spectrum | splash10-0569-2900000000-7820ea736b03b71d2cb8 | Spectrum | GC-MS | Nicotinic acid, non-derivatized, GC-MS Spectrum | splash10-0kmi-7900000000-9e4efda763cce5ddfe57 | Spectrum | GC-MS | Nicotinic acid, non-derivatized, GC-MS Spectrum | splash10-053i-0900000000-5daf0093df6c21c7279f | Spectrum | GC-MS | Nicotinic acid, non-derivatized, GC-MS Spectrum | splash10-053i-0900000000-f38b6609b45de8c74565 | Spectrum | GC-MS | Nicotinic acid, non-derivatized, GC-MS Spectrum | splash10-0540-0900000000-4f55c81a6cd42f1b961d | Spectrum | GC-MS | Nicotinic acid, non-derivatized, GC-MS Spectrum | splash10-057r-5900000000-00bf3662b5b9db533c0a | Spectrum | GC-MS | Nicotinic acid, non-derivatized, GC-MS Spectrum | splash10-0569-2900000000-7820ea736b03b71d2cb8 | Spectrum | GC-MS | Nicotinic acid, non-derivatized, GC-MS Spectrum | splash10-0540-0900000000-a701904fe6ded0abd98f | Spectrum | Predicted GC-MS | Nicotinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-05i0-9700000000-d7620f1dc8f42d1498b9 | Spectrum | Predicted GC-MS | Nicotinic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-05fr-9600000000-c3303cf4e83870b3e656 | Spectrum | Predicted GC-MS | Nicotinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Nicotinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-00di-1900000000-27508608b33f1fb9f221 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-003r-9100000000-a2037c9695659dceabd1 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0ufr-9100000000-4a2649a83ad2a40e5194 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive | splash10-0kmi-7900000000-1bc47d1b1850f54fb7c2 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-00di-1900000000-a352c5ce16d4b682b052 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-004i-9000000000-ab23ecb032e387b40bd9 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-004i-9000000000-02e37a1cfd3947037579 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-004i-9000000000-75d7e6658d2d6eca736e | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0udi-9000000000-21a2d68d4f364c596f1d | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-0ab9-0900000000-a74db528f61c435876c8 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-00di-6900000000-773c08ab92ace4d48a9c | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-00aj-9100000000-07b12fbe942e6c7fb12d | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-005a-9000000000-66e0a5ba2ca8dbba1ed5 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-004i-9000000000-fbf8ba47b56d7cc7be81 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-00di-0900000000-eaf82f6ab0befde118e9 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive | splash10-00di-0900000000-eaf82f6ab0befde118e9 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-004i-9300000000-b1a48f694fba565108a1 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00di-1900000000-a352c5ce16d4b682b052 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-9000000000-ab23ecb032e387b40bd9 | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-0900000000-25068c42378f72756922 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00di-3900000000-6278a1e122005f48fcaf | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ue9-9000000000-e4e41ed9bef32955889e | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-4900000000-85d44ecd8ad348eeacd1 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9300000000-4911305982583ae20895 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-4dea4a2d4a55907605ea | 2016-09-12 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 2D NMR | [1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 913 |
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ChEMBL ID | CHEMBL573 |
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KEGG Compound ID | C00253 |
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Pubchem Compound ID | 938 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 15940 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB00627 |
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HMDB ID | HMDB01488 |
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CRC / DFC (Dictionary of Food Compounds) ID | BPB04-S:BPB04-S |
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EAFUS ID | 2661 |
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Dr. Duke ID | NICOTINIC-ACID|NIACIN |
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BIGG ID | 34401 |
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KNApSAcK ID | C00000208 |
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HET ID | NIO |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Niacin |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | |
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Enzymes | Name | Gene Name | UniProt ID |
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G-protein coupled receptor 109B | GPR109B | P49019 | G-protein coupled receptor 109A | GPR109A | Q8TDS4 | Purine nucleoside phosphorylase | PNP | P00491 |
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Pathways | |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008). — U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page. — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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