Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:10:12 UTC |
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Update date | 2020-09-17 15:38:55 UTC |
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Primary ID | FDB012485 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Nicotinamide |
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Description | Niacinamide, also known as nicotinamid or nicovit, belongs to the class of organic compounds known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group. Niacinamide is a strong basic compound (based on its pKa). Niacinamide exists in all living species, ranging from bacteria to humans. niacinamide and phosphoribosyl pyrophosphate can be converted into nicotinic acid mononucleotide and phosphate through the action of the enzyme nicotinamide phosphoribosyltransferase. In humans, niacinamide is involved in the metabolic disorder called the nad+ signalling pathway (cancer). Niacinamide is an odorless tasting compound. Outside of the human body, Niacinamide is found, on average, in the highest concentration within a few different foods, such as common sages, milk (cow), and cocoa beans and in a lower concentration in common pea and beers. Niacinamide has also been detected, but not quantified in, several different foods, such as pineappple sages, boysenberries, cashew nuts, macadamia nut (m. tetraphylla), and sweet marjorams. This could make niacinamide a potential biomarker for the consumption of these foods. Niacinamide is a potentially toxic compound. A pyridinecarboxamide that is pyridine in which the hydrogen at position 3 is replaced by a carboxamide group. |
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CAS Number | 98-92-0 |
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Structure | |
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Synonyms | Synonym | Source |
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3-Pyridinecarboxamide | ChEBI | beta-Pyridinecarboxamide | ChEBI | Niacin | ChEBI | Nicotinamid | ChEBI | Nicotinic acid amide | ChEBI | Nicotinsaeureamid | ChEBI | Nikotinamid | ChEBI | Nikotinsaeureamid | ChEBI | Vitamin b3 | ChEBI | Vitamin PP | ChEBI | Nicotinamide | Kegg | b-Pyridinecarboxamide | Generator | Β-pyridinecarboxamide | Generator | Nicotinate amide | Generator | 3-Carbamoylpyridine | HMDB | 3-Pyridinecarboxylic acid amide | HMDB | Acid amide | HMDB | Amid kyseliny nikotinove | HMDB | Amide PP | HMDB | Aminicotin | HMDB | Amixicotyn | HMDB | Amnicotin | HMDB | Austrovit PP | HMDB | Benicot | HMDB | Delonin amide | HMDB | Dipegyl | HMDB | Dipigyl | HMDB | Endobion | HMDB | Factor PP | HMDB | Hansamid | HMDB | Inovitan PP | HMDB | m-(Aminocarbonyl)pyridine | HMDB | Mediatric | HMDB | NAM | HMDB | Nandervit-N | HMDB | Niacevit | HMDB | Niamide | HMDB | Niavit PP | HMDB | Nicamide | HMDB | Nicamina | HMDB | Nicamindon | HMDB | Nicasir | HMDB | Nicobion | HMDB | Nicofort | HMDB | Nicogen | HMDB | Nicomidol | HMDB | Nicosan 2 | HMDB | Nicosylamide | HMDB | Nicota | HMDB | Nicotamide | HMDB | Nicotilamide | HMDB | Nicotililamido | HMDB | Nicotinamida | HMDB | Nicotinamidum | HMDB | Nicotine acid amide | HMDB | Nicotine amide | HMDB | Nicotinic amide | HMDB | Nicotinsaureamid | HMDB | Nicotol | HMDB | Nicotylamide | HMDB | Nicotylamidum | HMDB | Nicovel | HMDB | Nicovit | HMDB | Nicovitina | HMDB | Nicovitol | HMDB | Nicozymin | HMDB | Nictoamide | HMDB | Niko-tamin | HMDB | Niocinamide | HMDB | Niozymin | HMDB | Papulex | HMDB | Pelmin | HMDB | Pelmine | HMDB | Pelonin amide | HMDB | PP-Faktor | HMDB | Propamine a | HMDB | Pyridine-3-carboxylic acid amide | HMDB | Savacotyl | HMDB | Vi-nicotyl | HMDB | Vi-noctyl | HMDB | Witamina PP | HMDB | 3 Pyridinecarboxamide | HMDB | Astra brand OF niacinamide | HMDB | b 3, Vitamin | HMDB | Niacinamide merck brand | HMDB | Pharmagenix brand OF niacinamide | HMDB | b3, Vitamin | HMDB | Enduramide | HMDB | Jenapharm, nicotinsäureamid | HMDB | Niacinamide jenapharm brand | HMDB | Niacinamide pharmagenix brand | HMDB | Jenapharm brand OF niacinamide | HMDB | Nicotinsäureamid jenapharm | HMDB | Vitamin b 3 | HMDB | Merck brand OF niacinamide | HMDB | Niacinamide astra brand | HMDB | Niacinamide | ChEBI | β-Pyridinecarboxamide | biospider | 3-(Aminocarbonyl)pyridine | biospider | 3-Amidopyridine | biospider | 6-Aminonicotinamide | biospider | Vitamin B3 (Nicotinamide) | biospider | Vitamin PP (Nicotinamide) | biospider | β-pyridinecarboxamide | Generator |
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Predicted Properties | |
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Chemical Formula | C6H6N2O |
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IUPAC name | pyridine-3-carboxamide |
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InChI Identifier | InChI=1S/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9) |
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InChI Key | DFPAKSUCGFBDDF-UHFFFAOYSA-N |
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Isomeric SMILES | NC(=O)C1=CC=CN=C1 |
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Average Molecular Weight | 122.1246 |
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Monoisotopic Molecular Weight | 122.048012824 |
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Classification |
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Description | Belongs to the class of organic compounds known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide 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 | Nicotinamides |
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Alternative Parents | |
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Substituents | - Nicotinamide
- Heteroaromatic compound
- Primary carboxylic acid amide
- Carboxamide group
- Azacycle
- 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 | Biological role: Industrial application: |
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Physico-Chemical Properties - Experimental |
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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 59.01%; H 4.95%; N 22.94%; O 13.10% | DFC |
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Melting Point | Mp 129-130° | DFC |
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Boiling Point | Bp0.0005 150-160° | DFC |
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Experimental Water Solubility | 500 mg/mL at 25 oC | MERCK INDEX (1996) |
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Experimental logP | -0.37 | HANSCH,C ET AL. (1995) |
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Experimental pKa | pKa 3.33 (20°) | 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-9600000000-2b1c5667d92bc1b80b36 | Spectrum | GC-MS | Nicotinamide, 1 TMS, GC-MS Spectrum | splash10-004i-0900000000-acb6a21304b0c09c8472 | Spectrum | GC-MS | Nicotinamide, non-derivatized, GC-MS Spectrum | splash10-004r-0900000000-ce86dcff0153b66dd538 | Spectrum | GC-MS | Nicotinamide, 1 TMS, GC-MS Spectrum | splash10-004i-9500000000-790385e574240b8d39de | Spectrum | GC-MS | Nicotinamide, 2 TMS, GC-MS Spectrum | splash10-0udi-2910000000-d760b65bb76d6464038e | Spectrum | GC-MS | Nicotinamide, 1 TMS, GC-MS Spectrum | splash10-004i-4900000000-47c6f72d1bb5465c1376 | Spectrum | GC-MS | Nicotinamide, non-derivatized, GC-MS Spectrum | splash10-0kor-9800000000-1809e537780b814af0c9 | Spectrum | GC-MS | Nicotinamide, non-derivatized, GC-MS Spectrum | splash10-0kor-9800000000-c4a5ff5285417499eff8 | Spectrum | GC-MS | Nicotinamide, non-derivatized, GC-MS Spectrum | splash10-004i-0900000000-0e84a60cc2a2d44704f4 | Spectrum | GC-MS | Nicotinamide, non-derivatized, GC-MS Spectrum | splash10-004i-0900000000-acb6a21304b0c09c8472 | Spectrum | GC-MS | Nicotinamide, non-derivatized, GC-MS Spectrum | splash10-004r-0900000000-ce86dcff0153b66dd538 | Spectrum | GC-MS | Nicotinamide, non-derivatized, GC-MS Spectrum | splash10-004i-9500000000-790385e574240b8d39de | Spectrum | GC-MS | Nicotinamide, non-derivatized, GC-MS Spectrum | splash10-0udi-2910000000-d760b65bb76d6464038e | Spectrum | GC-MS | Nicotinamide, non-derivatized, GC-MS Spectrum | splash10-004i-4900000000-47c6f72d1bb5465c1376 | Spectrum | GC-MS | Nicotinamide, non-derivatized, GC-MS Spectrum | splash10-004i-0900000000-23a567506bfbc259e77c | Spectrum | Predicted GC-MS | Nicotinamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-05fr-8900000000-931c139355be3ef594f2 | Spectrum | Predicted GC-MS | Nicotinamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Nicotinamide, 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-2900000000-72a7c92eb2667f5b6c3f | Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-001i-9000000000-6486d230a4a2fd4bab0e | Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-001i-9000000000-6486d230a4a2fd4bab0e | Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive | splash10-0kor-9800000000-89d56b6cb7e033699d24 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-00di-0900000000-eed71abbb10ba926c13d | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-00di-3900000000-0c62aa6aba6e23b6c195 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-001i-9100000000-4357a8833611d1756c59 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-001i-9000000000-c9685717817d0081fe6d | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-0fc0-9000000000-ec0ccca306f38cf72a78 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-00di-4900000000-f6d71a6c467f84ddd6ab | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive | splash10-001i-9100000000-62c4bd312efbfa37d1a1 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-00di-4900000000-05714b528dc84942b9db | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive | splash10-001i-9100000000-edb6a77c0dfdcbdacc5d | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-00di-0900000000-eed71abbb10ba926c13d | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-00di-3900000000-0c62aa6aba6e23b6c195 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-001i-9100000000-4357a8833611d1756c59 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-001i-9000000000-c9685717817d0081fe6d | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0fc0-9000000000-ec0ccca306f38cf72a78 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-00di-0900000000-960acce7ead55399b5db | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-0900000000-2c7ec333d35eb740520a | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0089-9600000000-466f98885e2efba73575 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ue9-9200000000-6ef8d7e5edcdd0b02758 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-1900000000-f38177aa475e58941088 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00fr-9800000000-6a883d82fcd7c450f6ce | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-882d0c59d946a5087b9f | Spectrum |
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NMR | |
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External Links |
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ChemSpider ID | 911 |
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ChEMBL ID | CHEMBL1140 |
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KEGG Compound ID | C00153 |
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Pubchem Compound ID | 936 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 17154 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB02701 |
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HMDB ID | HMDB01406 |
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CRC / DFC (Dictionary of Food Compounds) ID | HHJ27-Z:HHJ27-Z |
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EAFUS ID | 2662 |
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Dr. Duke ID | NICOTINIC-ACID-AMIDE|NICOTINAMIDE |
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BIGG ID | 34058 |
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KNApSAcK ID | C00000209 |
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HET ID | NCA |
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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 | rw1068911 |
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SuperScent ID | Not Available |
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Wikipedia ID | Niacinamide |
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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 | Descriptor | ID | Definition | Reference |
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cancer preventive | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | depressant | | | DUKE | antioxidant | 22586 | A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. | CHEBI |
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Enzymes | Name | Gene Name | UniProt ID |
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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 | Flavor | Citations |
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odorless |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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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 | — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181. — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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