1.0 2011-09-21 01:38:15 UTC 2015-07-21 06:59:23 UTC FDB028341 1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide 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) [HMDB] 1-(b-D-Ribofuranosyl)-1,4-dihydronicotinamide 1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide 1-(beta-delta-Ribofuranosyl)-1,4-dihydronicotinamide 1-(β-D-ribofuranosyl)-1,4-dihydronicotinamide Reduced nicotinamide riboside C11H16N2O5 256.2551 256.105921632 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,4-dihydropyridine-3-carboxamide reduced nicotinamide riboside NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O 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 MAKBMGXNXXXBFE-TURQNECASA-N 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). Glycosylamines Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic heteromonocyclic compounds Azacyclic compounds Carbonyl compounds Dihydropyridines Enamines Hydrocarbon derivatives N-substituted nicotinamides Organic oxides Organopnictogen compounds Oxacyclic compounds Pentoses Primary alcohols Primary carboxylic acid amides Secondary alcohols Tetrahydrofurans Vinylogous amides Alcohol Aliphatic heteromonocyclic compound Azacycle Carbonyl group Carboxamide group Carboxylic acid derivative Dihydropyridine Enamine Hydrocarbon derivative Hydropyridine Monosaccharide N-glycosyl compound N-substituted nicotinamide Organic nitrogen compound Organic oxide Organoheterocyclic compound Organonitrogen compound Organopnictogen compound Oxacycle Pentose monosaccharide Primary alcohol Primary carboxylic acid amide Secondary alcohol Tetrahydrofuran Vinylogous amide dihydropyridine pyridine nucleoside Solid logp -1.94 ALOGPS logs -0.50 ALOGPS solubility 8.05e+01 g/l ALOGPS logp -2.1 ChemAxon pka_strongest_acidic 12.56 ChemAxon pka_strongest_basic 3.89 ChemAxon iupac 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,4-dihydropyridine-3-carboxamide ChemAxon average_mass 256.2551 ChemAxon mono_mass 256.105921632 ChemAxon smiles NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O ChemAxon formula C11H16N2O5 ChemAxon inchi 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 ChemAxon inchikey MAKBMGXNXXXBFE-TURQNECASA-N ChemAxon polar_surface_area 116.25 ChemAxon refractivity 61.84 ChemAxon polarizability 24.92 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 16486 Specdb::CMs 39740 Specdb::CMs 133201 Specdb::CMs 140935 Specdb::NmrOneD 93792 Specdb::NmrOneD 93793 Specdb::NmrOneD 93794 Specdb::NmrOneD 93795 Specdb::NmrOneD 93796 Specdb::NmrOneD 93797 Specdb::NmrOneD 93798 Specdb::NmrOneD 93799 Specdb::NmrOneD 93800 Specdb::NmrOneD 93801 Specdb::NmrOneD 93802 Specdb::NmrOneD 93803 Specdb::NmrOneD 93804 Specdb::NmrOneD 93805 Specdb::NmrOneD 93806 Specdb::NmrOneD 93807 Specdb::NmrOneD 93808 Specdb::NmrOneD 93809 Specdb::NmrOneD 93810 Specdb::NmrOneD 93811 Specdb::MsMs 302425 Specdb::MsMs 302426 Specdb::MsMs 302427 Specdb::MsMs 345151 Specdb::MsMs 345152 Specdb::MsMs 345153 Specdb::MsMs 2704703 Specdb::MsMs 2704704 Specdb::MsMs 2704705 Specdb::MsMs 3004269 Specdb::MsMs 3004270 Specdb::MsMs 3004271 HMDB11648 #<Reference:0x000055ce3214ed98> #<Reference:0x000055ce3214be40> #<Reference:0x000055ce3214bc88> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823