Record Information
Version2.0
Creation Date2012-05-31 13:01:40 -0600
Update Date2015-06-03 15:53:36 -0600
Secondary Accession Numbers
  • ECMDB00855
Identification
Name:Nicotinamide riboside
DescriptionNicotinamide 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
Thumb
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]-1λ⁵-pyridin-1-ylium
Traditional IUPAC Name:nicotinamide ribose
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).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentGlycosylamines
Alternative Parents
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 FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility5.45 g/LALOGPS
logP-2.3ALOGPS
logP-6.1ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)11.39ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.89 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity60.83 m³·mol⁻¹ChemAxon
Polarizability24.73 ųChemAxon
Number of Rings2ChemAxon
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:
  • Nicotinate and nicotinamide metabolism ec00760
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-070f-9530000000-71d9e02ee640bb800185View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0a6r-9825400000-99de0fc632f408e32a12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-e25d1beb47cb1fe9e4cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-3090000000-03687e9ef697eda1d6c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052g-9300000000-2755bde4df843d2227f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-809be1146b2a2c8d96a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1390000000-2fc72cf0619f182e044fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0k96-9300000000-4d5b96b192f3484b1b8aView in MoNA
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
External Links:
ResourceLink
CHEBI ID15927
HMDB IDHMDB00855
Pubchem Compound ID439924
Kegg IDC03150
ChemSpider ID388956
Wikipedia IDNicotinamide riboside
BioCyc IDNICOTINAMIDE_RIBOSE
EcoCyc IDNICOTINAMIDE_RIBOSE
Ligand ExpoNNR

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Degradation of external UDP-glucose to uridine monophosphate and glucose-1-phosphate, which can then be used by the cell
Gene Name:
ushA
Uniprot ID:
P07024
Molecular weight:
60824
Reactions
UDP-sugar + H(2)O = UMP + alpha-D-aldose 1-phosphate.
A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate.
General function:
Involved in hydrolase activity
Specific function:
Nucleotidase with a broad substrate specificity as it can dephosphorylate various ribo- and deoxyribonucleoside 5'- monophosphates and ribonucleoside 3'-monophosphates with highest affinity to 3'-AMP. Also hydrolyzes polyphosphate (exopolyphosphatase activity) with the preference for short-chain- length substrates (P20-25). Might be involved in the regulation of dNTP and NTP pools, and in the turnover of 3'-mononucleotides produced by numerous intracellular RNases (T1, T2, and F) during the degradation of various RNAs. Also plays a significant physiological role in stress-response and is required for the survival of E.coli in stationary growth phase
Gene Name:
surE
Uniprot ID:
P0A840
Molecular weight:
26900
Reactions
A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate.
A 3'-ribonucleotide + H(2)O = a ribonucleoside + phosphate.
(Polyphosphate)(n) + H(2)O = (polyphosphate)(n-1) + phosphate.
General function:
Involved in catalytic activity
Specific function:
Nucleotidase that shows high phosphatase activity toward three nucleoside 5'-monophosphates, UMP, dUMP, and dTMP, and very low activity against TDP, IMP, UDP, GMP, dGMP, AMP, dAMP, and 6- phosphogluconate. Is strictly specific to substrates with 5'- phosphates and shows no activity against nucleoside 2'- or 3'- monophosphates. Might be involved in the pyrimidine nucleotide substrate cycles
Gene Name:
yjjG
Uniprot ID:
P0A8Y1
Molecular weight:
25300
Reactions
A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate.
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 negative regulation of transcription, DNA-dependent
Specific function:
NadR is bifunctional; it interacts with pnuC at low internal NAD levels, permitting transport of NMN intact into the cell. As NAD levels increase within the cell, the affinity of nadR for the operator regions of nadA, nadB, and pncB increases, repressing the transcription of these genes
Gene Name:
nadR
Uniprot ID:
P27278
Molecular weight:
47346
Reactions
ATP + nicotinamide ribonucleotide = diphosphate + NAD(+).
ATP + N-ribosylnicotinamide = ADP + nicotinamide ribonucleotide.
General function:
Involved in catalytic activity
Specific function:
Nucleotidase that shows strict specificity toward deoxyribonucleoside 5'-monophosphates and does not dephosphorylate 5'-ribonucleotides or ribonucleoside 3'-monophosphates. Might be involved in the regulation of all dNTP pools in E.coli
Gene Name:
yfbR
Uniprot ID:
P76491
Molecular weight:
22708
Reactions
A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate.

Transporters

General function:
Involved in transport
Specific function:
Required for nicotinamide riboside transport across the inner membrane
Gene Name:
pnuC
Uniprot ID:
P0AFK2
Molecular weight:
26996