| Record Information |
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:10:29 -0700 |
| HMDB ID |
HMDB01406 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
| Common Name |
Niacinamide |
| 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. |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- 3-Carbamoylpyridine
- 3-Pyridinecarboxamide
- 3-Pyridinecarboxylic acid amide
- 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
- 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-carboxylic acid amide
- Savacotyl
- Vi-Nicotyl
- Vi-noctyl
- Vitamin B3
- Vitamin PP
- Witamina PP
|
| Chemical Formula |
C6H6N2O |
| Average Molecular Weight |
122.1246 |
| Monoisotopic Molecular Weight |
122.048012824 |
| IUPAC Name |
pyridine-3-carboxamide |
| Traditional IUPAC Name |
nicotinamide |
| CAS Registry Number |
98-92-0 |
| 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 Key |
DFPAKSUCGFBDDF-UHFFFAOYSA-N |
| Chemical Taxonomy |
| Kingdom |
Organic Compounds |
| Super Class |
Aromatic Heteromonocyclic Compounds |
| Class |
Pyridines and Derivatives |
| Sub Class |
N/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 Parent |
Pyridines and Derivatives |
| Ontology |
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
- Component of Nicotinate and nicotinamide metabolism
|
| Application |
Not Available |
| Cellular locations |
|
| Physical Properties |
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| 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) |
|
| Predicted Properties |
|
| Spectra |
|
| 13C NMR Spectrum |
| 1H NMR Spectrum |
| MS/MS Spectrum Quattro_QQQ 10 |
| MS/MS Spectrum Quattro_QQQ 25 |
| MS/MS Spectrum Quattro_QQQ 40 |
| MS/MS Spectrum EI-B (HITACHI M-80) |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50 |
| MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) |
| MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies ) |
| MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) |
| MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) |
| MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30 |
| MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) |
| [1H,1H] 2D NMR Spectrum |
| [1H,13C] 2D NMR Spectrum |
|
| Biological Properties |
| Cellular Locations |
|
| Biofluid Locations |
|
| Tissue Location |
- Bladder
- Fibroblasts
- Neuron
- Pancreas
- Placenta
- Prostate
- Skin
- Spleen
- Stratum Corneum
|
| Pathways |
| Name |
SMPDB Link |
KEGG Link |
| Nicotinate and Nicotinamide Metabolism |
SMP00048
|
map00760
|
|
| Normal Concentrations |
|
| Blood |
Detected and Quantified |
|
0.44 +/- 0.0054 uM |
Adult (>18 years old) |
Both |
Normal
|
|
| Urine |
Detected and Quantified |
|
0.30 +/- 0.51 umol/mmol creatinine |
Infant (0-1 year old) |
Both |
Normal
|
|
|
| Abnormal Concentrations |
|
Not Available |
| Associated Disorders and Diseases |
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
| DrugBank ID |
DB02701  |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB012485 |
| KNApSAcK ID |
C00000209  |
| Chemspider ID |
911  |
| KEGG Compound ID |
C00153  |
| BioCyc ID |
NIACINAMIDE  |
| BiGG ID |
34058  |
| Wikipedia Link |
Niacinamide  |
| NuGOwiki Link |
HMDB01406  |
| Metagene Link |
HMDB01406  |
| METLIN ID |
1497  |
| PubChem Compound |
936  |
| PDB ID |
NCA  |
| ChEBI ID |
17154  |
| References |
| 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)
|
| General References |
- 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
- 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;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
- 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
- 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
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| Enzymes |
| Name: |
Nicotinamide N-methyltransferase
|
| Reactions: |
- S-Adenosylmethionine + Niacinamide unknown S-Adenosylhomocysteine + 1-Methylnicotinamide
- S-Adenosylmethionine + Niacinamide + Hydrogen Ion unknown S-Adenosylhomocysteine + 1-Methylnicotinamide
|
| Gene Name: |
NNMT |
| Uniprot ID: |
P40261  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
Tankyrase-2
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| Reactions: |
- NAD + (ADP-D-ribosyl)(n)-acceptor unknown Niacinamide + (ADP-D-ribosyl)(n+1)-acceptor
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| Gene Name: |
TNKS2 |
| Uniprot ID: |
Q9H2K2  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Ecto-ADP-ribosyltransferase 3
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| Reactions: |
- NAD + protein-L-arginine unknown Niacinamide + N(omega)-(ADP-D-ribosyl)-protein-L-arginine
- NADP + protein-L-arginine unknown Niacinamide + N(omega)-((2'-phospho-ADP)-D-ribosyl)-protein-L-arginine
|
| Gene Name: |
ART3 |
| Uniprot ID: |
Q13508  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
Ecto-ADP-ribosyltransferase 5
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| Reactions: |
- NAD + protein-L-arginine unknown Niacinamide + N(omega)-(ADP-D-ribosyl)-protein-L-arginine
- NADP + protein-L-arginine unknown Niacinamide + N(omega)-((2'-phospho-ADP)-D-ribosyl)-protein-L-arginine
|
| Gene Name: |
ART5 |
| Uniprot ID: |
Q96L15  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
|
|
| Name: |
Tankyrase-1
|
| Reactions: |
- NAD + (ADP-D-ribosyl)(n)-acceptor unknown Niacinamide + (ADP-D-ribosyl)(n+1)-acceptor
|
| Gene Name: |
TNKS |
| Uniprot ID: |
O95271  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
ADP-ribosyl cyclase 2
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| Reactions: |
- NAD + Water unknown Adenosine diphosphate ribose + Niacinamide
- NADP + Water unknown Niacinamide + (E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid
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| Gene Name: |
BST1 |
| Uniprot ID: |
Q10588  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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|
| Name: |
ADP-ribosyl cyclase 1
|
| Reactions: |
- NAD + Water unknown Adenosine diphosphate ribose + Niacinamide
- NADP + Water unknown Niacinamide + (E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid
|
| Gene Name: |
CD38 |
| Uniprot ID: |
P28907  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
Ecto-ADP-ribosyltransferase 4
|
| Reactions: |
- NAD + protein-L-arginine unknown Niacinamide + N(omega)-(ADP-D-ribosyl)-protein-L-arginine
- NADP + protein-L-arginine unknown Niacinamide + N(omega)-((2'-phospho-ADP)-D-ribosyl)-protein-L-arginine
|
| Gene Name: |
ART4 |
| Uniprot ID: |
Q93070  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Cytochrome P450 3A4
|
| Reactions: |
- Quinine + NADPH + Oxygen unknown 3-Hydroxyquinine + NADP + Water
- Taurochenodesoxycholic acid + NADPH + Oxygen unknown Taurohyocholate + NADP + Water
- Lithocholic acid + NADPH + Oxygen unknown Hyodeoxycholic acid + NADP + Water
- Albendazole + NADPH + Oxygen unknown albendazole S-oxide + NADP + Water
- Eucalyptol + NADPH + Oxygen unknown 2-exo-hydroxy-1,8-cineole + NADP + Water
|
| Gene Name: |
CYP3A4 |
| Uniprot ID: |
P08684  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
Cytochrome P450 2E1
|
| Reactions: |
- 4-Nitrophenol + NADPH + Oxygen unknown 4-Nitrocatechol + NADP + Water
|
| Gene Name: |
CYP2E1 |
| Uniprot ID: |
P05181  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
Cytochrome P450 2D6
|
| Reactions: |
- RH + reduced flavoprotein + Oxygen unknown ROH + oxidized flavoprotein + Water
|
| Gene Name: |
CYP2D6 |
| Uniprot ID: |
P10635  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
L-lactate dehydrogenase A chain
|
| Reactions: |
- L-Lactic acid + NAD unknown Pyruvic acid + NADH
- L-Lactic acid + NAD unknown Pyruvic acid + NADH + Hydrogen Ion
- 2-Hydroxybutyric acid + NAD unknown 2-Ketobutyric acid + NADH + Hydrogen Ion
- 3-Mercaptolactic acid + NAD unknown 3-Mercaptopyruvic acid + NADH + Hydrogen Ion
|
| Gene Name: |
LDHA |
| Uniprot ID: |
P00338  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
Purine nucleoside phosphorylase
|
| Reactions: |
- Nebularine + Phosphoric acid unknown Purine + Ribose 1-phosphate
- Adenosine + Phosphoric acid unknown Adenine + Ribose 1-phosphate
- Inosine + Phosphoric acid unknown Hypoxanthine + Ribose 1-phosphate
- Deoxyguanosine + Phosphoric acid unknown Guanine + Deoxyribose 1-phosphate
- Guanosine + Phosphoric acid unknown Guanine + Ribose 1-phosphate
- Nicotinamide riboside + Phosphoric acid unknown Niacinamide + Ribose 1-phosphate
- Nicotinate D-ribonucleoside + Phosphoric acid unknown Nicotinic acid + Ribose 1-phosphate + Hydrogen Ion
- Xanthosine + Phosphoric acid unknown Xanthine + Ribose 1-phosphate
- Deoxyuridine + Phosphoric acid unknown Uracil + Deoxyribose 1-phosphate
- Deoxyadenosine + Phosphoric acid unknown Adenine + Deoxyribose 1-phosphate
- Deoxyinosine + Phosphoric acid unknown Hypoxanthine + Deoxyribose 1-phosphate
|
| Gene Name: |
PNP |
| Uniprot ID: |
P00491  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
tRNA 2'-phosphotransferase 1
|
| Reactions: |
- 2'-phospho-[ligated tRNA] + NAD unknown mature tRNA + ADP ribose 1'',2''-phosphate + Niacinamide + Water
|
| Gene Name: |
TRPT1 |
| Uniprot ID: |
Q86TN4  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|