Showing Metabocard for 1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide (BASm0002519)
| Common Name | 1-(beta-d-ribofuranosyl)-1,4-dihydronicotinamide |
|---|---|
| Description | 1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide is the reduced form of nicotinamide riboside. Nicotinamide riboside or NR is a natural product found in milk. It can exist in both the oxidized and reduced form. Nicotinamide riboside is a newly discovered precursor to NAD ( nicotinamide adenine dinucleotide). Nicotinamide riboside kinases (Nrks) are essential for this NAD synthesis pathway. Nrks actually constitute a distinct pathway of NAD biosynthesis and it appears that nicotinamide riboside may be the only vitamin precursor that supports neuronal NAD synthesis (PMID: 18429699 ). NAD homeostasis is related to the free radical-mediated production of reactive oxygen species responsible for irreversible cellular damage in infectious disease, diabetes, inflammatory syndromes, neurodegeneration and cancer. (PMID: 18508649 ). Baseline requirements for NAD synthesis can be met either with dietary tryptophan or with less than 20 mg of daily niacin, which consists of nicotinic acid and/or nicotinamide. Reduced nicotinamide riboside is also known to be a substrate for ribosyldihydronicotinamide dehydrogenase (EC 1.10.99.2). It is also a substrate for purine-nucleoside phosphorylase (PNP) - (PMID: 9030766 ). |
| Structure | |
| Molecular Formula | C11H16N2O5 |
| Average Mass | 256.25510 |
| Monoisotopic Mass | 256.10592 |
| IUPAC Name | 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,4-dihydropyridine-3-carboxamide |
| Traditional Name | 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4h-pyridine-3-carboxamide |
| CAS Registry Number | Not Available |
| SMILES | NC(=O)C1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C=CC1 |
| InChI Identifier | InChI=1S/C11H16N2O5/c12-10(17)6-2-1-3-13(4-6)11-9(16)8(15)7(5-14)18-11/h1,3-4,7-9,11,14-16H,2,5H2,(H2,12,17)/t7-,8-,9-,11-/m1/s1 |
| InChI Key | MAKBMGXNXXXBFE-TURQNECASA-N |
| CHEBI ID | CHEBI:55458 |
| HMDB ID | HMDB0011648 |
| State | Solid |
| Water Solubility | 8.05e+01 g/l |
| logP | -1.94 |
| logS | -0.50 |
| pKa (Strongest Acidic) | 12.56 |
| pKa (Strongest Basic) | 3.89 |
| Hydrogen Acceptor Count | 6 |
| Hydrogen Donor Count | 4 |
| Polar Surface Area | 116.25 Ų |
| Rotatable Bond Count | 3 |
| Physiological Charge | 0 |
| Formal Charge | 0 |
| Refractivity | 61.84 m³·mol⁻¹ |
| Polarizability | 24.92 |