1.0 2016-09-30 22:37:34 UTC 2020-05-21 16:28:55 UTC BMDB0000855 BMDB00855 Nicotinamide riboside Nicotinamide riboside, also known as N-ribosylnicotinamide or SRT-647, 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). Nicotinamide riboside is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Nicotinamide riboside exists in all living species, ranging from bacteria to humans. Nicotinamide riboside participates in a number of enzymatic reactions, within cattle. In particular, Nicotinamide riboside and phosphoric acid can be biosynthesized from niacinamide and ribose-1-arsenate; which is mediated by the enzyme purine nucleoside phosphorylase. In addition, Nicotinamide riboside can be converted into nicotinamide ribotide; which is catalyzed by the enzyme cytosolic purine 5'-nucleotidase. In cattle, nicotinamide riboside is involved in the metabolic pathway called the nicotinate and nicotinamide metabolism pathway. 1-(beta-D-Ribofuranosyl)nicotinamide beta-Nicotinamide D-riboside Nicotinamide ribonucleoside Nicotinamide ribose Nicotinamide-beta-riboside N-Ribosylnicotinamide 1-(b-D-Ribofuranosyl)nicotinamide 1-(Β-D-ribofuranosyl)nicotinamide b-Nicotinamide D-riboside Β-nicotinamide D-riboside Nicotinamide-b-riboside Nicotinamide-β-riboside 1-b-D-Ribosyl-3-pyridinecarboxamide 1-beta-D-Ribosyl-3-pyridinecarboxamide 1-beta-delta-Ribosyl-3-pyridinecarboxamide 3-(Aminocarbonyl)-1-beta-D-ribofuranosyl-pyridinium 3-(Aminocarbonyl)-1-beta-delta-ribofuranosyl-pyridinium Ribosylnicotinamide SRT-647 SRT 647 C11H15N2O5 255.2472 255.0980966 3-carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1lambda5-pyridin-1-ylium 3-carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1lambda5-pyridin-1-ylium 1341-23-7 NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O 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 JLEBZPBDRKPWTD-TURQNECASA-O 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). Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Glycosylamines Azacyclic compounds Heteroaromatic compounds Hydrocarbon derivatives Nicotinamides Organic cations Organic oxides Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Pentoses Primary alcohols Primary carboxylic acid amides Pyridinium derivatives Secondary alcohols Tetrahydrofurans Vinylogous amides Alcohol Aromatic heteromonocyclic compound Azacycle Carboxamide group Carboxylic acid derivative Heteroaromatic compound Hydrocarbon derivative Monosaccharide N-glycosyl compound Nicotinamide Organic cation Organic nitrogen compound Organic oxide Organoheterocyclic compound Organonitrogen compound Organopnictogen compound Oxacycle Pentose monosaccharide Primary alcohol Primary carboxylic acid amide Pyridine Pyridine carboxylic acid or derivatives Pyridinium Secondary alcohol Tetrahydrofuran Vinylogous amide Aromatic heteromonocyclic compounds N-glycosylnicotinamide pyridine nucleoside Solid logp -2.27 ALOGPS logs -1.73 ALOGPS logp -6.1 ChemAxon pka_strongest_acidic 11.39 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac 3-carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1lambda5-pyridin-1-ylium ChemAxon average_mass 255.2472 ChemAxon mono_mass 255.0980966 ChemAxon smiles NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O ChemAxon formula C11H15N2O5 ChemAxon 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 ChemAxon inchikey JLEBZPBDRKPWTD-TURQNECASA-O ChemAxon polar_surface_area 116.89 ChemAxon refractivity 60.83 ChemAxon polarizability 24.83 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge 1 ChemAxon formal_charge 1 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Nicotinate and Nicotinamide Metabolism SMP0087241 Specdb::MsMs 26606 Specdb::MsMs 26607 Specdb::MsMs 26608 Specdb::MsMs 33164 Specdb::MsMs 33165 Specdb::MsMs 33166 Specdb::MsMs 1476600 Specdb::MsMs 1476601 Specdb::MsMs 1476602 Specdb::MsMs 1476603 Specdb::MsMs 1476604 Specdb::MsMs 1476605 Specdb::MsMs 1476606 Specdb::MsMs 1476607 Specdb::MsMs 1476608 Specdb::MsMs 1476609 Specdb::MsMs 1476610 Specdb::MsMs 1476611 Specdb::MsMs 1476612 Specdb::MsMs 1476613 Specdb::MsMs 1476614 Specdb::MsMs 1476615 Specdb::MsMs 1476616 Specdb::MsMs 1476617 Specdb::MsMs 1476618 Specdb::NmrOneD 145570 Specdb::NmrOneD 145571 Specdb::NmrOneD 145572 Specdb::NmrOneD 145573 Specdb::NmrOneD 145574 Specdb::NmrOneD 145575 Specdb::NmrOneD 145576 Specdb::NmrOneD 145577 Specdb::NmrOneD 145578 Specdb::NmrOneD 145579 Specdb::NmrOneD 145580 Specdb::NmrOneD 145581 Specdb::NmrOneD 145582 Specdb::NmrOneD 145583 Specdb::NmrOneD 145584 Specdb::NmrOneD 145585 Specdb::NmrOneD 145586 Specdb::NmrOneD 145587 Specdb::NmrOneD 145588 Specdb::NmrOneD 145589 Specdb::CMs 2996 Specdb::CMs 37806 Specdb::CMs 164946 Specdb::CMs 1080280 Specdb::CMs 1080281 Specdb::CMs 1080283 Specdb::CMs 1080285 Specdb::CMs 1080287 Specdb::CMs 1080289 Specdb::CMs 1080290 Specdb::CMs 1080292 Specdb::CMs 1080294 Specdb::CMs 1080296 Specdb::CMs 1080297 Specdb::CMs 1080299 Specdb::CMs 1080301 Specdb::CMs 1080303 Specdb::CMs 1080305 Specdb::CMs 1080307 Specdb::CMs 1080309 Specdb::CMs 1080310 Specdb::CMs 1080312 Specdb::CMs 1080314 Specdb::CMs 1080316 Specdb::CMs 1080318 Liver Metabolomics analysis was performed using GC-MS/LC-MS in multiparous Holstein dairy cows Shahzad K, Lopreiato V, Liang Y, Trevisi E, Osorio JS, Xu C, Loor JJ: Hepatic metabolomics and transcriptomics to study susceptibility to ketosis in response to prepartal nutritional management. J Anim Sci Biotechnol. 2019 Dec 18;10:96. doi: 10.1186/s40104-019-0404-z. eCollection 2019. 31867104 Milk Detected but not quantified in conventional whole milk Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386 Milk Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8 Placenta Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 FDB022281 388956 439924 C03150 15927 Nicotinamide riboside NICOTINAMIDE_RIBOSE 41300 5818 Franchetti, Palmarisa; Pasqualini, Michela; Petrelli, Riccardo; Ricciutelli, Massimo; Vita, Patrizia; Cappellacci, Loredana. Stereoselective synthesis of nicotinamide b-riboside and nucleoside analogs. Bioorganic & Medicinal Chemistry Letters (2004), 14(18), 4655-4658 Yang, T, Chan NY, Sauve AA. Syntheses of nicotinamide riboside and deriviatives.. J. Med Chem. 50:6458-61 (2007).. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386 Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8 BMDBP00149 Cytosolic purine 5'-nucleotidase O46411 NT5C2 Enzyme BMDBP00698 Purine nucleoside phosphorylase P55859 PNP Enzyme