Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:10:29 UTC
HMDB IDHMDB01406
Secondary Accession NumbersNone
Metabolite Identification
Common NameNiacinamide
DescriptionNiacinamide 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.
Structure
Thumb
Synonyms
  1. 3-Carbamoylpyridine
  2. 3-Pyridinecarboxamide
  3. 3-Pyridinecarboxylic acid amide
  4. Acid amide
  5. Amid kyseliny nikotinove
  6. Amide PP
  7. Aminicotin
  8. Amixicotyn
  9. Amnicotin
  10. Austrovit PP
  11. b-Pyridinecarboxamide
  12. Benicot
  13. beta-Pyridinecarboxamide
  14. Delonin Amide
  15. Dipegyl
  16. Dipigyl
  17. Endobion
  18. Factor pp
  19. Hansamid
  20. Inovitan PP
  21. m-(Aminocarbonyl)pyridine
  22. Mediatric
  23. NAM
  24. Nandervit-N
  25. Niacevit
  26. Niacinamide
  27. Niamide
  28. Niavit PP
  29. Nicamide
  30. Nicamina
  31. Nicamindon
  32. Nicasir
  33. Nicobion
  34. Nicofort
  35. Nicogen
  36. Nicomidol
  37. Nicosan 2
  38. Nicosylamide
  39. Nicota
  40. Nicotamide
  41. Nicotilamide
  42. Nicotililamido
  43. Nicotinamida
  44. Nicotinamide
  45. Nicotinamidum
  46. Nicotine acid amide
  47. Nicotine amide
  48. Nicotinic acid amide
  49. Nicotinic amide
  50. Nicotinsaureamid
  51. Nicotol
  52. Nicotylamide
  53. Nicotylamidum
  54. Nicovel
  55. Nicovit
  56. Nicovitina
  57. Nicovitol
  58. Nicozymin
  59. Nictoamide
  60. Niko-tamin
  61. Nikotinamid
  62. Nikotinsaeureamid
  63. Niocinamide
  64. Niozymin
  65. Papulex
  66. Pelmin
  67. Pelmine
  68. Pelonin amide
  69. PP-Faktor
  70. Propamine A
  71. Pyridine-3-carboxylic acid amide
  72. Savacotyl
  73. Vi-Nicotyl
  74. Vi-noctyl
  75. Vitamin B3
  76. Vitamin PP
  77. Witamina PP
Chemical FormulaC6H6N2O
Average Molecular Weight122.1246
Monoisotopic Molecular Weight122.048012824
IUPAC Namepyridine-3-carboxamide
Traditional IUPAC Namenicotinamide
CAS Registry Number98-92-0
SMILES
NC(=O)C1=CN=CC=C1
InChI Identifier
InChI=1S/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9)
InChI KeyDFPAKSUCGFBDDF-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteromonocyclic Compounds
ClassPyridines and Derivatives
Sub ClassN/A
Other Descriptors
  • Pyridine alkaloids(KEGG)
  • Water-soluble vitamins(KEGG)
  • a vitamin(Cyc)
  • an aliphatic amide(Cyc)
  • pyridine alkaloid(ChEBI)
  • pyridinecarboxamide(ChEBI)
Substituents
  • Carboxamide Group
  • Primary Carboxylic Acid Amide
Direct ParentPyridines and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Nicotinate and nicotinamide metabolism
ApplicationNot Available
Cellular locations
  • Extracellular
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point130 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility500 mg/mL at 25 °CNot Available
LogP-0.37HANSCH,C ET AL. (1995)
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 area55.98ChemAxon
rotatable bond count1ChemAxon
refractivity32.98ChemAxon
polarizability11.71ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Bladder
  • Fibroblasts
  • Neuron
  • Pancreas
  • Placenta
  • Prostate
  • Skin
  • Spleen
  • Stratum Corneum
Pathways
NameSMPDB LinkKEGG Link
Nicotinate and Nicotinamide MetabolismSMP00048map00760
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.44 +/- 0.0054 uMAdult (>18 years old)BothNormal
UrineDetected and Quantified0.30 +/- 0.51 umol/mmol creatinineInfant (0-1 year old)BothNormal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02701
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012485
KNApSAcK IDC00000209
Chemspider ID911
KEGG Compound IDC00153
BioCyc IDNIACINAMIDE
BiGG ID34058
Wikipedia LinkNiacinamide
NuGOwiki LinkHMDB01406
Metagene LinkHMDB01406
METLIN ID1497
PubChem Compound936
PDB IDNCA
ChEBI ID17154
References
Synthesis ReferenceGalat, Alexander. Nicotinamide from nicotinonitrile by catalytic hydration. Journal of the American Chemical Society (1948), 70 3945.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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
  2. 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
  3. 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
  4. 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
  5. Final report of the safety assessment of niacinamide and niacin. Int J Toxicol. 2005;24 Suppl 5:1-31. Pubmed: 16596767
  6. 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
  7. 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
  8. 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
  9. 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
  10. 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
  11. 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
  12. Anisimov AG, Bolotnikov IA: [Nicotinamide decreases DNA destabilization in K562 cells treated with AlF(-4)] Tsitologiia. 1997;39(9):822-8. Pubmed: 9518388
  13. 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
  14. 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
  15. 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
  16. 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
  17. 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
  18. 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
  19. 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

Enzymes

Gene Name:
NNMT
Uniprot ID:
P40261
Reactions
S-Adenosylmethionine + Niacinamide unknown S-Adenosylhomocysteine + 1-Methylnicotinamidedetails
S-Adenosylmethionine + Niacinamide + Hydrogen Ion unknown S-Adenosylhomocysteine + 1-Methylnicotinamidedetails
Gene Name:
TNKS2
Uniprot ID:
Q9H2K2
Reactions
NAD + (ADP-D-ribosyl)(n)-acceptor unknown Niacinamide + (ADP-D-ribosyl)(n+1)-acceptordetails
Gene Name:
SIRT6
Uniprot ID:
Q8N6T7
Reactions
NAD + an acetylprotein unknown Niacinamide + O-acetyl-ADP-ribose + a proteindetails
Gene Name:
PARP3
Uniprot ID:
Q9Y6F1
Reactions
NAD + (ADP-D-ribosyl)(n)-acceptor unknown Niacinamide + (ADP-D-ribosyl)(n+1)-acceptordetails
Gene Name:
ART3
Uniprot ID:
Q13508
Reactions
NAD + protein-L-arginine unknown Niacinamide + N(omega)-(ADP-D-ribosyl)-protein-L-argininedetails
NADP + protein-L-arginine unknown Niacinamide + N(omega)-((2'-phospho-ADP)-D-ribosyl)-protein-L-argininedetails
Gene Name:
ART5
Uniprot ID:
Q96L15
Reactions
NAD + protein-L-arginine unknown Niacinamide + N(omega)-(ADP-D-ribosyl)-protein-L-argininedetails
NADP + protein-L-arginine unknown Niacinamide + N(omega)-((2'-phospho-ADP)-D-ribosyl)-protein-L-argininedetails
Gene Name:
ART1
Uniprot ID:
P52961
Reactions
NAD + protein-L-arginine unknown Niacinamide + N(omega)-(ADP-D-ribosyl)-protein-L-argininedetails
NADP + protein-L-arginine unknown Niacinamide + N(omega)-((2'-phospho-ADP)-D-ribosyl)-protein-L-argininedetails
Gene Name:
TNKS
Uniprot ID:
O95271
Reactions
NAD + (ADP-D-ribosyl)(n)-acceptor unknown Niacinamide + (ADP-D-ribosyl)(n+1)-acceptordetails
Gene Name:
PARP1
Uniprot ID:
P09874
Reactions
NAD + (ADP-D-ribosyl)(n)-acceptor unknown Niacinamide + (ADP-D-ribosyl)(n+1)-acceptordetails
Gene Name:
BST1
Uniprot ID:
Q10588
Reactions
NAD + Water unknown Adenosine diphosphate ribose + Niacinamidedetails
NADP + Water unknown Niacinamide + (E)-3-(2,3-Dihydroxyphenyl)-2-propenoic aciddetails
Gene Name:
PARP2
Uniprot ID:
Q9UGN5
Reactions
NAD + (ADP-D-ribosyl)(n)-acceptor unknown Niacinamide + (ADP-D-ribosyl)(n+1)-acceptordetails
Gene Name:
CD38
Uniprot ID:
P28907
Reactions
NAD + Water unknown Adenosine diphosphate ribose + Niacinamidedetails
NADP + Water unknown Niacinamide + (E)-3-(2,3-Dihydroxyphenyl)-2-propenoic aciddetails
Gene Name:
ART4
Uniprot ID:
Q93070
Reactions
NAD + protein-L-arginine unknown Niacinamide + N(omega)-(ADP-D-ribosyl)-protein-L-argininedetails
NADP + protein-L-arginine unknown Niacinamide + N(omega)-((2'-phospho-ADP)-D-ribosyl)-protein-L-argininedetails
Gene Name:
PARP4
Uniprot ID:
Q9UKK3
Reactions
NAD + (ADP-D-ribosyl)(n)-acceptor unknown Niacinamide + (ADP-D-ribosyl)(n+1)-acceptordetails
Gene Name:
CYP3A4
Uniprot ID:
P08684
Gene Name:
CYP2E1
Uniprot ID:
P05181
Gene Name:
CYP2D6
Uniprot ID:
P10635
Gene Name:
LDHA
Uniprot ID:
P00338
Gene Name:
PNP
Uniprot ID:
P00491
Reactions
Nicotinamide riboside + Phosphoric acid unknown Niacinamide + Ribose 1-phosphatedetails
Gene Name:
NAMPT
Uniprot ID:
P43490
Reactions
beta-nicotinamide D-ribonucleotide + Pyrophosphate unknown Niacinamide + Phosphoribosyl pyrophosphatedetails
Gene Name:
PARP10
Uniprot ID:
Q53GL7
Reactions
NAD + (ADP-D-ribosyl)(n)-acceptor unknown Niacinamide + (ADP-D-ribosyl)(n+1)-acceptordetails
Gene Name:
PARP11
Uniprot ID:
Q9NR21
Reactions
NAD + (ADP-D-ribosyl)(n)-acceptor unknown Niacinamide + (ADP-D-ribosyl)(n+1)-acceptordetails
Gene Name:
PARP12
Uniprot ID:
Q9H0J9
Reactions
NAD + (ADP-D-ribosyl)(n)-acceptor unknown Niacinamide + (ADP-D-ribosyl)(n+1)-acceptordetails
Gene Name:
PARP14
Uniprot ID:
Q460N5
Reactions
NAD + (ADP-D-ribosyl)(n)-acceptor unknown Niacinamide + (ADP-D-ribosyl)(n+1)-acceptordetails
Gene Name:
PARP15
Uniprot ID:
Q460N3
Reactions
NAD + (ADP-D-ribosyl)(n)-acceptor unknown Niacinamide + (ADP-D-ribosyl)(n+1)-acceptordetails
Gene Name:
PARP16
Uniprot ID:
Q8N5Y8
Reactions
NAD + protein-L-arginine unknown Niacinamide + N(omega)-(ADP-D-ribosyl)-protein-L-argininedetails
Gene Name:
PARP6
Uniprot ID:
Q2NL67
Reactions
NAD + (ADP-D-ribosyl)(n)-acceptor unknown Niacinamide + (ADP-D-ribosyl)(n+1)-acceptordetails
Gene Name:
PARP8
Uniprot ID:
Q8N3A8
Reactions
NAD + (ADP-D-ribosyl)(n)-acceptor unknown Niacinamide + (ADP-D-ribosyl)(n+1)-acceptordetails
Gene Name:
PARP9
Uniprot ID:
Q8IXQ6
Reactions
NAD + (ADP-D-ribosyl)(n)-acceptor unknown Niacinamide + (ADP-D-ribosyl)(n+1)-acceptordetails
Gene Name:
TIPARP
Uniprot ID:
Q7Z3E1
Reactions
NAD + (ADP-D-ribosyl)(n)-acceptor unknown Niacinamide + (ADP-D-ribosyl)(n+1)-acceptordetails
Gene Name:
SIRT1
Uniprot ID:
Q96EB6
Reactions
NAD + an acetylprotein unknown Niacinamide + O-acetyl-ADP-ribose + a proteindetails
Gene Name:
SIRT2
Uniprot ID:
Q8IXJ6
Reactions
NAD + an acetylprotein unknown Niacinamide + O-acetyl-ADP-ribose + a proteindetails
Gene Name:
SIRT3
Uniprot ID:
Q9NTG7
Reactions
NAD + an acetylprotein unknown Niacinamide + O-acetyl-ADP-ribose + a proteindetails
Gene Name:
SIRT4
Uniprot ID:
Q9Y6E7
Reactions
NAD + a protein unknown Niacinamide + an N-(ADP-D-ribosyl)-proteindetails
NAD + an acetylprotein unknown Niacinamide + O-acetyl-ADP-ribose + a proteindetails
Gene Name:
SIRT5
Uniprot ID:
Q9NXA8
Reactions
NAD + a malonylprotein unknown Niacinamide + O-malonyl-ADP-ribose + a proteindetails
NAD + a succinylprotein unknown Niacinamide + O-succinyl-ADP-ribose + a proteindetails
Gene Name:
SIRT7
Uniprot ID:
Q9NRC8
Reactions
NAD + an acetylprotein unknown Niacinamide + O-acetyl-ADP-ribose + a proteindetails
Gene Name:
TRPT1
Uniprot ID:
Q86TN4
Reactions
2'-phospho-[ligated tRNA] + NAD unknown mature tRNA + ADP ribose 1'',2''-phosphate + Niacinamide + Waterdetails