Nicotinamide riboside

Nicotinamide riboside
Names
IUPAC name
3-Carbamoyl-1-(β-D-ribofuranosyl)pyridin-1-ium
Systematic IUPAC name
3-Carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyridin-1-ium
Other names
1-(β-D-Ribofuranosyl)nicotinamide; N-Ribosylnicotinamide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C11H14N2O5/c12-10(17)6-2-1-3-13(4-6)11-9(16)8(15)7(5-14)18
  • c1cc(c[n+](c1)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)C(=O)N
Properties
C11H15N2O5+
Molar mass 255.25 g/mol
Melting point Complete thermal degradation occurs above 130°C (chloride salt)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Nicotinamide riboside (NR, SR647) is a pyridine-nucleoside and a form of vitamin B3. It functions as a precursor to nicotinamide adenine dinucleotide, or NAD+,[2] through a two-step and a three-step pathway.[3]

  1. ^ Campbell, MT; Jones, DS; Andrews, GP; Li, S (2019). "Understanding the physicochemical properties and degradation kinetics of nicotinamide riboside chloride" (PDF). Food & Nutrition Research. 63: 3419. doi:10.29219/fnr.v63.3419.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  2. ^ Bogan, KL; Brenner, C (2008). "Nicotinic acid, nicotinamide, and nicotinamide riboside: a molecular evaluation of NAD+ precursor vitamins in human nutrition". Annu. Rev. Nutr. 28: 115–130. doi:10.1146/annurev.nutr.28.061807.155443. PMID 18429699.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. ^ Mehmel, M; Jovanović, N; Spitz, U (31 May 2020). "Nicotinamide Riboside-The Current State of Research and Therapeutic Uses". Nutrients. 12 (6): 1616. doi:10.3390/nu12061616. PMC 7352172. PMID 32486488.