Record Information
Version2.0
Creation Date2012-05-31 13:51:56 -0600
Update Date2015-09-13 12:56:11 -0600
Secondary Accession Numbers
  • ECMDB01406
Identification
Name:Niacinamide
DescriptionNicotinamide, also known as niacinamide and nicotinic acid amide, is the amide of nicotinic acid (vitamin B3). Nicotinamide is a water-soluble vitamin and is part of the vitamin B group. In cells, niacin is incorporated into nicotinamide adenine dinucleotide (NAD) and nicotinamide adenine dinucleotide phosphate (NADP), although the pathways for nicotinamide and nicotinic acid are very similar. NAD+ and NADP+ are coenzymes in a wide variety of enzymatic oxidation-reduction reactions. (Wikipedia)
Structure
Thumb
Synonyms:
  • 3-Carbamoylpyridine
  • 3-Pyridinecarboxamide
  • 3-Pyridinecarboxylate amide
  • 3-Pyridinecarboxylic acid amide
  • 6-Aminonicotinamide
  • Acid amide
  • Amid kyseliny nikotinove
  • Amide PP
  • Aminicotin
  • Amixicotyn
  • Amnicotin
  • Austrovit PP
  • B-Pyridinecarboxamide
  • Benicot
  • Beta-Pyridinecarboxamide
  • Delonin Amide
  • Dipegyl
  • Dipigyl
  • Endobion
  • Factor pp
  • Hansamid
  • Inovitan PP
  • M-(Aminocarbonyl)pyridine
  • Mediatric
  • NAM
  • Nandervit-N
  • Niacevit
  • Niacinamide
  • Niamide
  • Niavit PP
  • Nicamide
  • Nicamina
  • Nicamindon
  • Nicasir
  • Nicobion
  • Nicofort
  • Nicogen
  • Nicomidol
  • Nicosan 2
  • Nicosylamide
  • Nicota
  • Nicotamide
  • Nicotilamide
  • Nicotililamido
  • Nicotinamida
  • Nicotinamide
  • Nicotinamidum
  • Nicotinate amide
  • Nicotine acid amide
  • Nicotine amide
  • Nicotinic acid amide
  • Nicotinic amide
  • Nicotinsaureamid
  • Nicotol
  • Nicotylamide
  • Nicotylamidum
  • Nicovel
  • Nicovit
  • Nicovitina
  • Nicovitol
  • Nicozymin
  • Nictoamide
  • Niko-tamin
  • Nikotinamid
  • Nikotinsaeureamid
  • Niocinamide
  • Niozymin
  • Papulex
  • Pelmin
  • Pelmine
  • Pelonin amide
  • PP-Faktor
  • Propamine A
  • Pyridine-3-carboxylate amide
  • Pyridine-3-carboxylic acid amide
  • Savacotyl
  • Vi-Nicotyl
  • Vi-noctyl
  • Vitamin B3
  • Vitamin PP
  • Witamina PP
  • β-Pyridinecarboxamide
Chemical Formula:C6H6N2O
Weight:Average: 122.1246
Monoisotopic: 122.048012824
InChI Key:DFPAKSUCGFBDDF-UHFFFAOYSA-N
InChI:InChI=1S/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9)
CAS number:98-92-0
IUPAC Name:pyridine-3-carboxamide
Traditional IUPAC Name:nicotinamide
SMILES:NC(=O)C1=CC=CN=C1
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridinecarboxylic acids and derivatives
Direct ParentNicotinamides
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Solid
Charge:0
Melting point:130 °C
Experimental Properties:
PropertyValueSource
Water Solubility:500 mg/mL at 25 oC [MERCK INDEX (1996)]PhysProp
LogP:-0.37 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility50.1 g/LALOGPS
logP-0.45ALOGPS
logP-0.39ChemAxon
logS-0.39ALOGPS
pKa (Strongest Acidic)13.39ChemAxon
pKa (Strongest Basic)3.63ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.98 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity32.98 m³·mol⁻¹ChemAxon
Polarizability11.71 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
NAD salvagePW000830 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
44± 0 uMBW2511348 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L GlucoStationary Phase, glucose limitedBioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h37 oCPMID: 17379776
Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-004i-0900000000-acb6a21304b0c09c8472View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-004r-0900000000-ce86dcff0153b66dd538View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-004i-9500000000-790385e574240b8d39deView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0udi-2910000000-d760b65bb76d6464038eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-004i-4900000000-47c6f72d1bb5465c1376View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0kor-9800000000-1809e537780b814af0c9View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0kor-9800000000-c4a5ff5285417499eff8View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-0900000000-0e84a60cc2a2d44704f4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0900000000-acb6a21304b0c09c8472View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004r-0900000000-ce86dcff0153b66dd538View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-9500000000-790385e574240b8d39deView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-2910000000-d760b65bb76d6464038eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004i-4900000000-47c6f72d1bb5465c1376View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0900000000-23a567506bfbc259e77cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fr-8900000000-931c139355be3ef594f2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-2900000000-72a7c92eb2667f5b6c3fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-6486d230a4a2fd4bab0eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-6486d230a4a2fd4bab0eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0kor-9800000000-89d56b6cb7e033699d24View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00di-0900000000-eed71abbb10ba926c13dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-3900000000-0c62aa6aba6e23b6c195View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-001i-9100000000-4357a8833611d1756c59View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-001i-9000000000-c9685717817d0081fe6dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0fc0-9000000000-ec0ccca306f38cf72a78View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-4900000000-f6d71a6c467f84ddd6abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-001i-9100000000-62c4bd312efbfa37d1a1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-4900000000-05714b528dc84942b9dbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-001i-9100000000-edb6a77c0dfdcbdacc5dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-0900000000-eed71abbb10ba926c13dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-3900000000-0c62aa6aba6e23b6c195View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9100000000-4357a8833611d1756c59View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-c9685717817d0081fe6dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0fc0-9000000000-ec0ccca306f38cf72a78View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0900000000-960acce7ead55399b5dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-2c7ec333d35eb740520aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0089-9600000000-466f98885e2efba73575View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-9200000000-6ef8d7e5edcdd0b02758View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1900000000-f38177aa475e58941088View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fr-9800000000-6a883d82fcd7c450f6ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-882d0c59d946a5087b9fView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0kor-9600000000-2b1c5667d92bc1b80b36View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Anisimov AG, Bolotnikov IA: [Nicotinamide decreases DNA destabilization in K562 cells treated with AlF(-4)] Tsitologiia. 1997;39(9):822-8. Pubmed: 9518388
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • Final report of the safety assessment of niacinamide and niacin. Int J Toxicol. 2005;24 Suppl 5:1-31. Pubmed: 16596767
  • 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
  • Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • 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
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • Sonee M, Martens JR, Mukherjee SK: Nicotinamide protects HCN2 cells from the free radical generating toxin, tertiary butylhydroperoxide (t-BuOOH). Neurotox Res. 2002 Nov;4(7-8):595-599. Pubmed: 12709297
  • 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. Pubmed: 19212411
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • 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
Synthesis Reference:Galat, Alexander. Nicotinamide from nicotinonitrile by catalytic hydration. Journal of the American Chemical Society (1948), 70 3945.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID17154
HMDB IDHMDB01406
Pubchem Compound ID936
Kegg IDC00153
ChemSpider ID911
WikipediaNiacinamide
BioCyc IDNIACINAMIDE
EcoCyc IDNIACINAMIDE
Ligand ExpoNCA

Enzymes

General function:
Involved in purine-nucleoside phosphorylase activity
Specific function:
Cleavage of guanosine or inosine to respective bases and sugar-1-phosphate molecules
Gene Name:
deoD
Uniprot ID:
P0ABP8
Molecular weight:
25950
Reactions
Purine nucleoside + phosphate = purine + alpha-D-ribose 1-phosphate.
General function:
Involved in catalytic activity
Specific function:
Nicotinamide + H(2)O = nicotinate + NH(3)
Gene Name:
pncA
Uniprot ID:
P21369
Molecular weight:
23362
Reactions
Nicotinamide + H(2)O = nicotinate + NH(3).
General function:
Not Available
Specific function:
Not Available
Gene Name:
cobB
Uniprot ID:
P75960
Molecular weight:
Not Available