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Nicotinamide riboside (YMDB00103)

Identification
YMDB IDYMDB00103
NameNicotinamide riboside
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionNicotinamide riboside, also known as N-ribosylnicotinamide or SRT-647, 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). Nicotinamide riboside is an extremely weak basic (essentially neutral) compound (based on its pKa). Nicotinamide riboside exists in all living species, ranging from bacteria to humans. Within yeast, nicotinamide riboside participates in a number of enzymatic reactions. In particular, nicotinamide riboside can be converted into nicotinamide ribotide; which is mediated by the enzyme nicotinamide riboside kinase. In addition, nicotinamide riboside can be converted into D-ribose and niacinamide through its interaction with the enzyme uridine nucleosidase. In yeast, nicotinamide riboside is involved in the metabolic pathway called the nad metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-(beta-D-Ribofuranosyl)nicotinamide
  • 1-b-D-ribosyl-3-Pyridinecarboxamide
  • 1-beta-D-ribosyl-3-Pyridinecarboxamide
  • 1-beta-delta-ribosyl-3-Pyridinecarboxamide
  • 3-(aminocarbonyl)-1-beta-D-ribofuranosyl-Pyridinium
  • 3-(aminocarbonyl)-1-beta-delta-ribofuranosyl-Pyridinium
  • N-Ribosylnicotinamide
  • Nicotinamide ribonucleoside
  • Nicotinamide ribose
  • Nicotinamide riboside
  • nicotinamide-beta-riboside
  • Ribosylnicotinamide
  • beta-Nicotinamide D-riboside
  • 1-(b-D-Ribofuranosyl)nicotinamide
  • 1-(Β-D-ribofuranosyl)nicotinamide
  • b-Nicotinamide D-riboside
  • Β-nicotinamide D-riboside
  • Nicotinamide-b-riboside
  • Nicotinamide-β-riboside
  • SRT-647
  • SRT 647
CAS number1341-23-7
WeightAverage: 255.2472
Monoisotopic: 255.0980966
InChI KeyJLEBZPBDRKPWTD-TURQNECASA-O
InChIInChI=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
IUPAC Name3-carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1lambda5-pyridin-1-ylium
Traditional IUPAC Name3-carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1lambda5-pyridin-1-ylium
Chemical FormulaC11H15N2O5
SMILES[H]OC([H])([H])[C@@]1([H])O[C@@]([H])([N+]2=C([H])C([H])=C([H])C(=C2[H])C(=O)N([H])[H])[C@]([H])(O[H])[C@]1([H])O[H]
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
StateSolid
Charge1
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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)-1.6ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.89 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity60.83 m³·mol⁻¹ChemAxon
Polarizability24.83 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
NAD metabolismPW002421 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Nicotinate and nicotinamide metabolismec00760 Map00760
SMPDB Reactions
Nicotinamide riboside + Adenosine triphosphate → Nicotinamide ribotide + ADP + hydron
Nicotinamide riboside + water → hydron + D-Ribose + Niacinamide
KEGG Reactions
phosphate + Nicotinamide riboside ↔ hydron + Niacinamide + Ribose 1-phosphate
Adenosine triphosphate + Nicotinamide riboside → hydron + Nicotinamide ribotide + ADP
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-070f-9530000000-71d9e02ee640bb800185JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0a6r-9825400000-99de0fc632f408e32a12JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_5) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_6) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_7) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0a4i-0190000000-51bf764225f08b566d36JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0a4i-0290000000-ffbe280293f874204044JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-05fr-0970000000-1714e669425e34d3754aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-00di-0920000000-77ef12950b3152d752c8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-00di-0900000000-b14d15851532222ba74aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-00di-0900000000-277d95be8f0485eb3ce5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-00di-0900000000-354c1f3978635e5109bbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-00di-0900000000-ea5e376f71c6414964bcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-00di-0900000000-6b289ae1c5f53e92f774JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-00di-1900000000-6ad92fa16e2cca17f959JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 12V, positivesplash10-00di-1900000000-cee8757ed6b406ccf044JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 15V, positivesplash10-00di-2900000000-78f21d967892a0d9ab85JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 19V, positivesplash10-00di-3900000000-cd1f66bfc8ded7bd098eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 22V, positivesplash10-00e9-8900000000-5a6bc8100043575c6a58JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 28V, positivesplash10-00ai-9200000000-aedd3c5bf179b666a6aeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 33V, positivesplash10-003r-9000000000-22053c801abdfaf5f562JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 41V, positivesplash10-0fai-9000000000-b6b4b7e819e08c863a9aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 17V, positivesplash10-00di-0900000000-3364e345334aa7f5a742JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 17V, positivesplash10-004i-9000000000-3bf262f96423e85a1756JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-e25d1beb47cb1fe9e4cbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-3090000000-03687e9ef697eda1d6c8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052g-9300000000-2755bde4df843d2227f2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-809be1146b2a2c8d96a7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1390000000-2fc72cf0619f182e044fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0k96-9300000000-4d5b96b192f3484b1b8aJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Belenky, P., Christensen, K. C., Gazzaniga, F., Pletnev, A. A., Brenner, C. (2009). "Nicotinamide riboside and nicotinic acid riboside salvage in fungi and mammals. Quantitative basis for Urh1 and purine nucleoside phosphorylase function in NAD+ metabolism." J Biol Chem 284:158-164.19001417
  • de Figueiredo, L. F., Gossmann, T. I., Ziegler, M., Schuster, S. (2011). "Pathway Analysis of NAD+ metabolism." Biochem J :.21729004
  • 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 117:495-502.15137942
  • Belenky, P., Racette, F. G., Bogan, K. L., McClure, J. M., Smith, J. S., Brenner, C. (2007). "Nicotinamide riboside promotes Sir2 silencing and extends lifespan via Nrk and Urh1/Pnp1/Meu1 pathways to NAD+." Cell 129:473-484.17482543
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
External Links:
ResourceLink
CHEBI ID15927
HMDB IDHMDB00855
Pubchem Compound ID439924
Kegg IDC03150
ChemSpider ID388956
FOODB IDFDB022281
WikipediaNicotinamide_riboside
BioCyc IDNICOTINAMIDE_RIBOSE

Enzymes

Protein Details
1. Nicotinamide riboside kinase
General function:
Involved in ATP binding
Specific function:
Catalyzes the phosphorylation of nicotinamide riboside (NR) and nicotinic acid riboside (NaR) to form nicotinamide mononucleotide (NMN) and nicotinic acid mononucleotide (NaMN)
Gene Name:
NRK1
Uniprot ID:
P53915
Molecular weight:
27689.30078
Reactions
ATP + N-ribosylnicotinamide → ADP + nicotinamide ribonucleotide.
ATP + D-ribosylnicotinate → ADP + nicotinate D-ribonucleotide.
Protein Details
2. Uridine nucleosidase
General function:
Involved in hydrolase activity, hydrolyzing N-glycosyl compounds
Specific function:
Also acts on cytidine
Gene Name:
URH1
Uniprot ID:
Q04179
Molecular weight:
37960.0
Reactions
Uridine + H(2)O → D-ribose + uracil.