| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:45:29 UTC |
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| Update Date | 2020-06-04 20:55:32 UTC |
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| BMDB ID | BMDB0001406 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Niacinamide |
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| Description | Niacinamide, also known as nicotinamid or vitamin B3, 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 exists as a solid, possibly soluble (in water), and a strong basic compound (based on its pKa) molecule. Niacinamide exists in all living species, ranging from bacteria to humans. Niacinamide participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylmethionine and niacinamide can be converted into S-adenosylhomocysteine and 1-methylnicotinamide through the action of the enzyme nicotinamide N-methyltransferase. In addition, Niacinamide and ribose-1-arsenate can be converted into nicotinamide riboside and phosphoric acid through its interaction with the enzyme purine nucleoside phosphorylase. In cattle, niacinamide is involved in the metabolic pathway called the nicotinate and nicotinamide metabolism pathway. Niacinamide is a potentially toxic compound. |
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| Structure | |
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| Synonyms | | Value | 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 |
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| Chemical Formula | C6H6N2O |
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| Average Molecular Weight | 122.1246 |
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| Monoisotopic Molecular Weight | 122.048012824 |
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| IUPAC Name | pyridine-3-carboxamide |
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| Traditional Name | nicotinamide |
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| CAS Registry Number | 98-92-0 |
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| SMILES | NC(=O)C1=CC=CN=C1 |
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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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| Chemical Taxonomy |
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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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| Status | Detected and Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | Not Available |
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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 | 130 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 500 mg/mL at 25 °C | Not Available | | LogP | -0.37 | HANSCH,C ET AL. (1995) |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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| Biological Properties |
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| Cellular Locations | Not Available |
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| Biospecimen Locations | - Bladder
- Epidermis
- Fibroblasts
- Liver
- Mammary Gland
- Milk
- Muscle
- Neuron
- Pancreas
- Placenta
- Prostate Tissue
- Spleen
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| Pathways | |
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| Normal Concentrations |
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| Bladder | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Epidermis | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Fibroblasts | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 5.6 +/- 2.5 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 5.2 +/- 3.4 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 7.3 +/- 1.5 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 10.6 +/- 0.2 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 10.4 +/- 0.2 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 11.3 +/- 0.2 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 10.3 +/- 0.3 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 5.7 +/- 0.7 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 5.4 +/- 0.4 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 5 +/- 2 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 7 +/- 1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 135.28 +/- 8.64 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 141.86 +/- 6.17 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 90.35 +/- 6.44 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 96.76 +/- 6.23 uM | Not Specified | Not Specified | Normal | | details | | Neuron | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Pancreas | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Prostate Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Spleen | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
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| Abnormal Concentrations |
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| Not Available |
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| External Links |
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| HMDB ID | HMDB0001406 |
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| DrugBank ID | DB02701 |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB012485 |
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| KNApSAcK ID | C00000209 |
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| Chemspider ID | 911 |
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| KEGG Compound ID | C00153 |
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| BioCyc ID | NIACINAMIDE |
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| BiGG ID | 34058 |
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| Wikipedia Link | Nicotinamide |
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| METLIN ID | 1497 |
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| PubChem Compound | 936 |
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| PDB ID | Not Available |
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| ChEBI ID | 17154 |
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| References |
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| Synthesis Reference | Galat, Alexander. Nicotinamide from nicotinonitrile by catalytic hydration. Journal of the American Chemical Society (1948), 70 3945. |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - Agostini TS, Scherer R, Godoy HT: Simultaneous determination of B-group vitamins in enriched Brazilian dairy products. Crit Rev Food Sci Nutr. 2007;47(5):435-9. doi: 10.1080/10408390600846309. [PubMed:17558655 ]
- Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
- Trammell SA, Yu L, Redpath P, Migaud ME, Brenner C: Nicotinamide Riboside Is a Major NAD+ Precursor Vitamin in Cow Milk. J Nutr. 2016 May;146(5):957-63. doi: 10.3945/jn.116.230078. Epub 2016 Apr 6. [PubMed:27052539 ]
- Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
- A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
- Superfoodly [Link]
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