Showing Metabocard for beta-nicotinamide D-riboside (BASm0000462)
| Common Name | Beta-nicotinamide d-riboside | ||||
|---|---|---|---|---|---|
| Description | Nicotinamide riboside is involved in nicotinate and nicotinamide metabolism. Nicotinamide riboside was originally identified as a nutrient in milk. It is a useful compound for the elevation of NAD+ levels in humans. Nicotinamide riboside has recently been discovered to be an NAD(+) precursor that is converted into nicotinamide mononucleotide by specific nicotinamide riboside kinases, Nrk1 and Nrk2. It has been shown that exogenous nicotinamide riboside promotes Sir2-dependent repression of recombination, improves gene silencing, and extends the lifespan of certain animal models without calorie restriction (PMID: 17482543 ). Supplementation in mammalian cells and mouse tissues increases NAD(+) levels and activates SIRT1 and SIRT3, culminating in enhanced oxidative metabolism and protection against high-fat diet-induced metabolic abnormalities (PMID: 22682224 ). Recent data suggest that nicotinamide riboside may be the only vitamin precursor that supports neuronal NAD+ synthesis (PMID: 18429699 ). Nicotinamide riboside kinase has an essential role in the phosphorylation of nicotinamide riboside and the cancer drug tiazofurin (PMID: 15137942 ). | ||||
| Structure | |||||
| Molecular Formula | C11H15N2O5 | ||||
| Average Mass | 255.24720 | ||||
| Monoisotopic Mass | 255.09810 | ||||
| IUPAC Name | 3-carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1$l^{5}-pyridin-1-ylium | ||||
| Traditional Name | Nicotinamide ribose | ||||
| CAS Registry Number | 1341-23-7 | ||||
| SMILES | NC(=O)c1ccc[n+]([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c1 | ||||
| InChI Identifier | 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 | ||||
| InChI Key | JLEBZPBDRKPWTD-TURQNECASA-O | ||||
| CHEBI ID | CHEBI:15927 | ||||
| HMDB ID | HMDB0000855 | ||||
| Pathways |
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| State | Solid | ||||
| Water Solubility | 5.45e+00 g/l | ||||
| logP | -2.27 | ||||
| logS | -1.73 | ||||
| pKa (Strongest Acidic) | 11.39 | ||||
| pKa (Strongest Basic) | -2.23 | ||||
| Hydrogen Acceptor Count | 5 | ||||
| Hydrogen Donor Count | 4 | ||||
| Polar Surface Area | 116.89 Ų | ||||
| Rotatable Bond Count | 3 | ||||
| Physiological Charge | 1 | ||||
| Formal Charge | 1 | ||||
| Refractivity | 60.83 m³·mol⁻¹ | ||||
| Polarizability | 24.73 |