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Record Information
Version	2.0
Creation Date	2012-05-31 13:01:40 -0600
Update Date	2015-06-03 15:53:36 -0600
Secondary Accession Numbers	ECMDB00855
Identification
Name:	Nicotinamide riboside
Description	Nicotinamide riboside is involved in nicotinate and nicotinamide metabolism. It is a reducible moiety of the coenzyme NAD+. Nicotinamide riboside kinase has an essential role for phosphorylation of nicotinamide riboside (PMID 15137942).
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xb0f69694> Close
Synonyms:	1-(β-D ribofuranosyl)nicotinamide 1-(b-D Ribofuranosyl)nicotinamide 1-(b-D-Ribofuranosyl)-nicotinamide 1-(b-D-Ribofuranosyl)nicotinamide 1-(beta-D Ribofuranosyl)nicotinamide 1-(beta-D-ribofuranosyl)-nicotinamide 1-(beta-D-Ribofuranosyl)nicotinamide 1-(β-D Ribofuranosyl)nicotinamide 1-(β-D-Ribofuranosyl)-nicotinamide 1-(β-D-Ribofuranosyl)nicotinamide 1-b-D-Ribosyl-3-Pyridinecarboxamide 1-b-delta-Ribosyl-3-pyridinecarboxamide 1-b-δ-Ribosyl-3-pyridinecarboxamide 1-beta-D-Ribosyl-3-Pyridinecarboxamide 1-beta-delta-Ribosyl-3-Pyridinecarboxamide 1-β-D-Ribosyl-3-pyridinecarboxamide 1-β-δ-Ribosyl-3-pyridinecarboxamide 3-(Aminocarbonyl)-1-b-D-ribofuranosyl-pyridinium 3-(Aminocarbonyl)-1-b-delta-ribofuranosyl-pyridinium 3-(Aminocarbonyl)-1-b-δ-ribofuranosyl-pyridinium 3-(Aminocarbonyl)-1-beta-D-ribofuranosyl-Pyridinium 3-(Aminocarbonyl)-1-beta-delta-ribofuranosyl-Pyridinium 3-(Aminocarbonyl)-1-β-D-ribofuranosyl-pyridinium 3-(Aminocarbonyl)-1-β-δ-ribofuranosyl-pyridinium N-ribosyl-nicotinamide N-Ribosyl-nicotinamide N-Ribosylnicotinamide Nicotinamide ribonucleoside Nicotinamide ribose Nicotinamide riboside Nicotinamide-b-riboside Nicotinamide-beta-riboside Nicotinamide-β-riboside Ribosylnicotinamide
Chemical Formula:	C11H15N2O5
Weight:	Average: 255.2472 Monoisotopic: 255.0980966
InChI Key:	JLEBZPBDRKPWTD-TURQNECASA-O
InChI:	InChI=1S/C11H14N2O5/c12-10(17)6-2-1-3-13(4-6)11-9(16)8(15)7(5-14)18-11/h1-4,7-9,11,14-16H,5H2,(H-,12,17)/p+1/t7-,8-,9-,11-/m1/s1
CAS number:	1341-23-7
IUPAC Name:	3-carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1lambda5-pyridin-1-ylium
Traditional IUPAC Name:	3-carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1lambda5-pyridin-1-ylium
SMILES:	NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).
Kingdom	Organic compounds
Super Class	Organic oxygen compounds
Class	Organooxygen compounds
Sub Class	Carbohydrates and carbohydrate conjugates
Direct Parent	Glycosylamines
Alternative Parents	Pentoses Nicotinamides Pyridinium derivatives Vinylogous amides Tetrahydrofurans Heteroaromatic compounds Secondary alcohols Primary carboxylic acid amides Azacyclic compounds Oxacyclic compounds Organic oxides Primary alcohols Hydrocarbon derivatives Organonitrogen compounds Organopnictogen compounds Organic cations
Substituents	N-glycosyl compound Pentose monosaccharide Nicotinamide Pyridine carboxylic acid or derivatives Monosaccharide Pyridine Pyridinium Vinylogous amide Heteroaromatic compound Tetrahydrofuran Secondary alcohol Carboxamide group Primary carboxylic acid amide Organoheterocyclic compound Oxacycle Azacycle Carboxylic acid derivative Hydrocarbon derivative Primary alcohol Organic oxide Organonitrogen compound Organopnictogen compound Alcohol Organic nitrogen compound Organic cation Aromatic heteromonocyclic compound
Molecular Framework	Aromatic heteromonocyclic compounds
External Descriptors	N-glycosylnicotinamide (CHEBI:15927 ) pyridine nucleoside (CHEBI:15927 )
Physical Properties
State:	Solid
Charge:	1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 5.45 g/L ALOGPS logP -2.3 ALOGPS logP -6.1 ChemAxon logS -1.7 ALOGPS pKa (Strongest Acidic) 11.39 ChemAxon pKa (Strongest Basic) -1.6 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 116.89 Ų ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 60.83 m³·mol⁻¹ ChemAxon Polarizability 24.83 ų ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	Nicotinamide riboside + Phosphate <> Niacinamide + alpha-D-Ribose 1-phosphate Nicotinamide ribotide + Water <> Nicotinamide riboside + Phosphate Nicotinamide riboside + Adenosine triphosphate > Hydrogen ion + Nicotinamide ribotide + ADP Adenosine triphosphate + Nicotinamide riboside > ADP + NMN Nicotinamide riboside + Adenosine triphosphate > Adenosine diphosphate + Hydrogen ion + beta-nicotinamide D-ribonucleotide + ADP + NMN
SMPDB Pathways:	NAD salvage PW000830
KEGG Pathways:	Nicotinate and nicotinamide metabolism ec00760
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-070f-9530000000-71d9e02ee640bb800185 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive splash10-0a6r-9825400000-99de0fc632f408e32a12 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_3_5) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_3_6) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_3_7) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - Orbitrap 0V, positive splash10-0a4i-0190000000-51bf764225f08b566d36 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 1V, positive splash10-0a4i-0290000000-ffbe280293f874204044 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 2V, positive splash10-05fr-0970000000-1714e669425e34d3754a View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 3V, positive splash10-00di-0920000000-77ef12950b3152d752c8 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 5V, positive splash10-00di-0900000000-b14d15851532222ba74a View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 6V, positive splash10-00di-0900000000-277d95be8f0485eb3ce5 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 7V, positive splash10-00di-0900000000-354c1f3978635e5109bb View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 8V, positive splash10-00di-0900000000-ea5e376f71c6414964bc View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 10V, positive splash10-00di-0900000000-6b289ae1c5f53e92f774 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 11V, positive splash10-00di-1900000000-6ad92fa16e2cca17f959 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 12V, positive splash10-00di-1900000000-cee8757ed6b406ccf044 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 15V, positive splash10-00di-2900000000-78f21d967892a0d9ab85 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 19V, positive splash10-00di-3900000000-cd1f66bfc8ded7bd098e View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 22V, positive splash10-00e9-8900000000-5a6bc8100043575c6a58 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 28V, positive splash10-00ai-9200000000-aedd3c5bf179b666a6ae View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 33V, positive splash10-003r-9000000000-22053c801abdfaf5f562 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 41V, positive splash10-0fai-9000000000-b6b4b7e819e08c863a9a View in MoNA LC-MS/MS LC-MS/MS Spectrum - n/a 17V, positive splash10-00di-0900000000-3364e345334aa7f5a742 View in MoNA LC-MS/MS LC-MS/MS Spectrum - n/a 17V, positive splash10-004i-9000000000-3bf262f96423e85a1756 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0a4i-0090000000-e25d1beb47cb1fe9e4cb View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-002b-3090000000-03687e9ef697eda1d6c8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-052g-9300000000-2755bde4df843d2227f2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0udi-0090000000-809be1146b2a2c8d96a7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0udi-1390000000-2fc72cf0619f182e044f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0k96-9300000000-4d5b96b192f3484b1b8a View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	Belenky P, Racette FG, Bogan KL, McClure JM, Smith JS, Brenner C: Nicotinamide riboside promotes Sir2 silencing and extends lifespan via Nrk and Urh1/Pnp1/Meu1 pathways to NAD+. Cell. 2007 May 4;129(3):473-84. Pubmed: 17482543 Bieganowski, P., Brenner, C. (2004). "Discoveries of nicotinamide riboside as a nutrient and conserved NRK genes establish a Preiss-Handler independent route to NAD+ in fungi and humans." Cell 117:495-502. Pubmed: 15137942 Bogan KL, Brenner C: Nicotinic acid, nicotinamide, and nicotinamide riboside: a molecular evaluation of NAD+ precursor vitamins in human nutrition. Annu Rev Nutr. 2008;28:115-30. doi: 10.1146/annurev.nutr.28.061807.155443. Pubmed: 18429699 Canto C, Houtkooper RH, Pirinen E, Youn DY, Oosterveer MH, Cen Y, Fernandez-Marcos PJ, Yamamoto H, Andreux PA, Cettour-Rose P, Gademann K, Rinsch C, Schoonjans K, Sauve AA, Auwerx J: The NAD(+) precursor nicotinamide riboside enhances oxidative metabolism and protects against high-fat diet-induced obesity. Cell Metab. 2012 Jun 6;15(6):838-47. doi: 10.1016/j.cmet.2012.04.022. Pubmed: 22682224 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 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 Magni G, Amici A, Emanuelli M, Orsomando G, Raffaelli N, Ruggieri S: Enzymology of NAD+ homeostasis in man. Cell Mol Life Sci. 2004 Jan;61(1):19-34. Pubmed: 14704851 Pankiewicz KW, Watanabe KA, Lesiak-Watanabe K, Goldstein BM, Jayaram HN: The chemistry of nicotinamide adenine dinucleotide (NAD) analogues containing C-nucleosides related to nicotinamide riboside. Curr Med Chem. 2002 Apr;9(7):733-41. Pubmed: 11966436 Schalk-Hihi C, Zhang YZ, Markham GD: The conformation of NADH bound to inosine 5'-monophosphate dehydrogenase determined by transferred nuclear Overhauser effect spectroscopy. Biochemistry. 1998 May 19;37(20):7608-16. Pubmed: 9585576 Wall KA, Klis M, Kornet J, Coyle D, Ame JC, Jacobson MK, Slama JT: Inhibition of the intrinsic NAD+ glycohydrolase activity of CD38 by carbocyclic NAD analogues. Biochem J. 1998 Nov 1;335 ( Pt 3):631-6. Pubmed: 9794804
Synthesis Reference:	Franchetti, Palmarisa; Pasqualini, Michela; Petrelli, Riccardo; Ricciutelli, Massimo; Vita, Patrizia; Cappellacci, Loredana. Stereoselective synthesis of nicotinamide b-riboside and nucleoside analogs. Bioorganic & Medicinal Chemistry Letters (2004), 1
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 15927 HMDB ID HMDB00855 Pubchem Compound ID 439924 Kegg ID C03150 ChemSpider ID 388956 Wikipedia ID Nicotinamide riboside BioCyc ID NICOTINAMIDE_RIBOSE EcoCyc ID NICOTINAMIDE_RIBOSE Ligand Expo NNR

Enzymes

Transporters