Record Information |
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Version | 4.0 |
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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 | 2018-03-28 17:00:15 UTC |
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HMDB ID | HMDB0001406 |
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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 or vitamin B3 is an important compound functioning as a component of the coenzyme NAD. Its primary significance is in the prevention and/or cure of blacktongue and pellagra. Most animals cannot manufacture this compound in amounts sufficient to prevent nutritional deficiency and it therefore must be supplemented through dietary intake. Niacinamide is used to increase the effect of radiation therapy on tumor cells. Niacin (nicotinic acid) and niacinamide, while both labeled as vitamin B3 also have different applications. Niacinamide is useful in arthritis and early-onset type I diabetes while niacin is an effective reducer of high cholesterol levels. |
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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 | 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 | Nicotinamide | 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 | MeSH | Astra brand OF niacinamide | MeSH | b 3, Vitamin | MeSH | Niacinamide merck brand | MeSH | Pharmagenix brand OF niacinamide | MeSH | b3, Vitamin | MeSH | Enduramide | MeSH | Jenapharm, nicotinsäureamid | MeSH | Niacinamide jenapharm brand | MeSH | Niacinamide pharmagenix brand | MeSH | Jenapharm brand OF niacinamide | MeSH | Nicotinsäureamid jenapharm | MeSH | Vitamin b 3 | MeSH | Merck brand OF niacinamide | MeSH | Niacinamide astra brand | MeSH |
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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 | This compound 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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Process | Naturally occurring process: |
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Role | Biological role: Industrial application: |
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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 | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS) | splash10-004i-0900000000-acb6a21304b0c09c8472 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-004r-0900000000-ce86dcff0153b66dd538 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS) | splash10-004i-9500000000-790385e574240b8d39de | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-0udi-2910000000-d760b65bb76d6464038e | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (1 TMS) | splash10-004i-4900000000-47c6f72d1bb5465c1376 | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0kor-9800000000-1809e537780b814af0c9 | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0kor-9800000000-c4a5ff5285417499eff8 | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-004i-0900000000-0e84a60cc2a2d44704f4 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-004i-0900000000-acb6a21304b0c09c8472 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-004r-0900000000-ce86dcff0153b66dd538 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-004i-9500000000-790385e574240b8d39de | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0udi-2910000000-d760b65bb76d6464038e | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-004i-4900000000-47c6f72d1bb5465c1376 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-004i-0900000000-23a567506bfbc259e77c | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-05fr-8900000000-931c139355be3ef594f2 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-00di-2900000000-72a7c92eb2667f5b6c3f | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-001i-9000000000-6486d230a4a2fd4bab0e | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-001i-9000000000-6486d230a4a2fd4bab0e | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive | splash10-0kor-9800000000-89d56b6cb7e033699d24 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-00di-0900000000-eed71abbb10ba926c13d | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-00di-3900000000-0c62aa6aba6e23b6c195 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-001i-9100000000-4357a8833611d1756c59 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-001i-9000000000-c9685717817d0081fe6d | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-0fc0-9000000000-ec0ccca306f38cf72a78 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-00di-4900000000-f6d71a6c467f84ddd6ab | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive | splash10-001i-9100000000-62c4bd312efbfa37d1a1 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-00di-4900000000-05714b528dc84942b9db | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive | splash10-001i-9100000000-edb6a77c0dfdcbdacc5d | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-00di-0900000000-eed71abbb10ba926c13d | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-00di-3900000000-0c62aa6aba6e23b6c195 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-001i-9100000000-4357a8833611d1756c59 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-001i-9000000000-c9685717817d0081fe6d | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0fc0-9000000000-ec0ccca306f38cf72a78 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-00di-0900000000-960acce7ead55399b5db | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-0900000000-2c7ec333d35eb740520a | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0089-9600000000-466f98885e2efba73575 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ue9-9200000000-6ef8d7e5edcdd0b02758 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-1900000000-f38177aa475e58941088 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00fr-9800000000-6a883d82fcd7c450f6ce | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-882d0c59d946a5087b9f | View in MoNA |
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MS | Mass Spectrum (Electron Ionization) | splash10-0kor-9600000000-2b1c5667d92bc1b80b36 | View in MoNA |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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General References | - Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
- Rybak ME, Pfeiffer CM: Clinical analysis of vitamin B(6): determination of pyridoxal 5'-phosphate and 4-pyridoxic acid in human serum by reversed-phase high-performance liquid chromatography with chlorite postcolumn derivatization. Anal Biochem. 2004 Oct 15;333(2):336-44. [PubMed:15450810 ]
- Draelos ZD, Ertel K, Berge C: Niacinamide-containing facial moisturizer improves skin barrier and benefits subjects with rosacea. Cutis. 2005 Aug;76(2):135-41. [PubMed:16209160 ]
- Soma Y, Kashima M, Imaizumi A, Takahama H, Kawakami T, Mizoguchi M: Moisturizing effects of topical nicotinamide on atopic dry skin. Int J Dermatol. 2005 Mar;44(3):197-202. [PubMed:15807725 ]
- Authors unspecified: Final report of the safety assessment of niacinamide and niacin. Int J Toxicol. 2005;24 Suppl 5:1-31. [PubMed:16596767 ]
- Draelos ZD, Matsubara A, Smiles K: The effect of 2% niacinamide on facial sebum production. J Cosmet Laser Ther. 2006 Jun;8(2):96-101. [PubMed:16766489 ]
- Schulpis K, Spiropoulos A, Gavrili S, Karikas G, Grigori C, Vlachos G, Papassotiriou I: Maternal - neonatal folate and vitamin B12 serum concentrations in Greeks and in Albanian immigrants. J Hum Nutr Diet. 2004 Oct;17(5):443-8. [PubMed:15357698 ]
- Yang L, Yao Y, Shi Y, Wang X, Shi J: [Expression of nicotinamide edenine dinucleotide dehydrogenase gene in placenta of patients with pregnancy induced hypertension]. Zhonghua Fu Chan Ke Za Zhi. 2002 Nov;37(11):660-2. [PubMed:12487919 ]
- Sonee M, Martens JR, Mukherjee SK: Nicotinamide protects HCN2 cells from the free radical generating toxin, tertiary butylhydroperoxide (t-BuOOH). Neurotox Res. 2002 Nov-Dec;4(7-8):595-599. [PubMed:12709297 ]
- Bayraktar F, Dereli D, Ozgen AG, Yilmaz C: Plasma homocysteine levels in polycystic ovary syndrome and congenital adrenal hyperplasia. Endocr J. 2004 Dec;51(6):601-8. [PubMed:15644580 ]
- Sonee M, Martens JR, Evers MR, Mukherjee SK: The effect of tertiary butylhydroperoxide and nicotinamide on human cortical neurons. Neurotoxicology. 2003 Jun;24(3):443-8. [PubMed:12782109 ]
- Anisimov AG, Bolotnikov IA: [Nicotinamide decreases DNA destabilization in K562 cells treated with AlF(-4)]. Tsitologiia. 1997;39(9):822-8. [PubMed:9518388 ]
- Matuoka K, Chen KY, Takenawa T: Rapid reversion of aging phenotypes by nicotinamide through possible modulation of histone acetylation. Cell Mol Life Sci. 2001 Dec;58(14):2108-16. [PubMed:11814060 ]
- Bartalena L, Tanda ML, Piantanida E, Lai A: Oxidative stress and Graves' ophthalmopathy: in vitro studies and therapeutic implications. Biofactors. 2003;19(3-4):155-63. [PubMed:14757966 ]
- Bissett DL, Oblong JE, Berge CA: Niacinamide: A B vitamin that improves aging facial skin appearance. Dermatol Surg. 2005 Jul;31(7 Pt 2):860-5; discussion 865. [PubMed:16029679 ]
- Baeza N, Moriscot C, Figarella C, Guy-Crotte O, Vialettes B: Reg protein: a potential beta-cell-specific growth factor? Diabetes Metab. 1996 Jul;22(4):229-34. [PubMed:8767167 ]
- Hoskin PJ, Rojas AM, Phillips H, Saunders MI: Acute and late morbidity in the treatment of advanced bladder carcinoma with accelerated radiotherapy, carbogen, and nicotinamide. Cancer. 2005 Jun 1;103(11):2287-97. [PubMed:15834926 ]
- Rembold CM: Combination therapy of dyslipidemia in non-insulin-dependent diabetes mellitus and the metabolic syndrome. Curr Diab Rep. 2004 Oct;4(5):330-4. [PubMed:15461896 ]
- Kawasaki E, Abiru N, Eguchi K: Prevention of type 1 diabetes: from the view point of beta cell damage. Diabetes Res Clin Pract. 2004 Dec;66 Suppl 1:S27-32. [PubMed:15563975 ]
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