Record Information |
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Version | 1.0 |
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Created at | 2020-04-17 18:50:23 UTC |
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Updated at | 2020-12-07 19:11:16 UTC |
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CannabisDB ID | CDB004918 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound Identification |
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Common 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. Nicotinic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it. |
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Structure | |
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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 | 123.11 |
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Monoisotopic Molecular Weight | 123.032 |
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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 | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Industrial application: Biological role: |
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Physical Properties |
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State | Solid |
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Experimental 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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Predicted Properties | [] |
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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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Pathways |
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Pathways | Name | SMPDB/Pathwhiz | KEGG | Nicotinate and Nicotinamide Metabolism | | |
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Protein Targets |
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Enzymes | |
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Transporters | |
Monocarboxylate transporter 1 | SLC16A1 | 1p12 | P53985 | details | Solute carrier family 22 member 5 | SLC22A5 | 5q31 | O76082 | details | Solute carrier organic anion transporter family member 2B1 | SLCO2B1 | 11q13 | O94956 | details |
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Metal Bindings | |
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Receptors | |
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Transcriptional Factors | Not Available |
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Concentrations Data |
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External Links |
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HMDB ID | HMDB0001488 |
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DrugBank ID | DB00627 |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB001014 |
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KNApSAcK ID | C00000208 |
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Chemspider ID | 913 |
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KEGG Compound ID | C00253 |
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BioCyc ID | NIACINE |
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BiGG ID | 34401 |
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Wikipedia Link | Niacin |
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METLIN ID | 6272 |
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PubChem Compound | 938 |
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PDB ID | Not Available |
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ChEBI ID | 15940 |
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References |
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General References | Not Available |
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