Nicotinamide riboside (PAMDB000194)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000194
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
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
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
Average Molecular Weight: 255.2472
Monoisotopic Molecular Weight: 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]-1???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
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as glycosylamines. These 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 ClassOrganooxygen compounds
Class Carbohydrates and carbohydrate conjugates
Sub ClassGlycosyl compounds
Direct Parent Glycosylamines
Alternative Parents
Substituents
  • N-glycosyl compound
  • Pyridine carboxylic acid or derivatives
  • Nicotinamide
  • Pyridinium
  • Pyridine
  • Monosaccharide
  • Heteroaromatic compound
  • Vinylogous amide
  • Oxolane
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Carboxamide group
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary alcohol
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility5.45 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity60.83 m3·mol-1ChemAxon
Polarizability24.73 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
Pathways:
  • Nicotinate and nicotinamide metabolism pae00760
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
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 IDNot Available
BioCyc IDNICOTINAMIDE_RIBOSE
EcoCyc IDNICOTINAMIDE_RIBOSE
Ligand ExpoNNR

Enzymes

Protein Details
• Multifunctional protein surE
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 Pseudomonas aeruginosa in stationary growth phase
Gene Name:
surE
Locus Tag:
PA3625
Molecular weight:
26.4 kDa
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.

Transporters