Nicotinamide riboside

Nicotinamide riboside

Names
Other names 1-(β-D-Ribofuranosyl)nicotinamide; N-Ribosylnicotinamide
Identifiers
CAS Number	1341-23-7
3D model (JSmol)	Interactive image
ChEBI	CHEBI:15927
ChemSpider	388956
KEGG	C03150
PubChem CID	439924
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 Key: JLEBZPBDRKPWTD-TURQNECASA-O
SMILES c1cc(c[n+](c1)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)C(=O)N
Properties
Chemical formula	C11H15N2O5+
Molar mass	255.25 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Nicotinamide riboside (NR) is a pyridine-nucleoside form of vitamin B₃ that functions as a precursor to nicotinamide adenine dinucleotide or NAD+. According to the peer-reviewed literature, NR was discovered as a human vitamin precursor of NAD+ in 2004 and as a sirtuin-activating compound in 2007 by Charles Brenner.

In 2016 the FDA granted generally recognized as safe (GRAS) status for NR as a food ingredient in enhanced water products, protein shakes, nutrition bars, gum and chews at no more than 0.027% of NR by weight. The NOAEL and LOAEL in rodents are 300 and 1000 mg/kg/day respectively.

While the molecular weight of nicotinamide riboside is 255.25 g/mol, that of its chloride salt is 290.70 g/mol. As such, 100 mg of nicotinamide riboside chloride provides 88 mg of nicotinamide riboside.

NR was first described in 1944 as a growth factor, termed Factor V, for Haemophilus influenza, a bacterium that lives in and depends on blood. Factor V, purified from blood was shown to exist in three forms: NAD+, NMN and NR. NR was the compound that led to the most rapid growth of this bacterium. Notably, H. influenza cannot grow on nicotinic acid, nicotinamide, tryptophan or aspartic acid, which were the previously known precursors of NAD+.

In 2000, yeast Sir2 was shown to be an NAD+-dependent protein lysine deacetylase, which led several groups to probe yeast NAD+ metabolism for genes and enzymes that might regulate lifespan. Biosynthesis of NAD+ in yeast was thought to flow exclusively through NAMN (nicotinic acid mononucleotide).