2.0 2012-05-31 13:01:40 -0600 2015-06-03 15:53:36 -0600 ECMDB00855 M2MDB000194 Nicotinamide riboside Nicotinamide riboside is involved in nicotinate and nicotinamide metabolism. It is a reducible moiety of the coenzyme NAD+. Nicotinamide riboside kinase has an essential role for phosphorylation of nicotinamide riboside (PMID 15137942). 1-(&beta;-D ribofuranosyl)nicotinamide 1-(b-D Ribofuranosyl)nicotinamide 1-(b-D-Ribofuranosyl)-nicotinamide 1-(b-D-Ribofuranosyl)nicotinamide 1-(beta-D Ribofuranosyl)nicotinamide 1-(beta-D-ribofuranosyl)-nicotinamide 1-(beta-D-Ribofuranosyl)nicotinamide 1-(β-D Ribofuranosyl)nicotinamide 1-(β-D-Ribofuranosyl)-nicotinamide 1-(β-D-Ribofuranosyl)nicotinamide 1-b-D-Ribosyl-3-Pyridinecarboxamide 1-b-delta-Ribosyl-3-pyridinecarboxamide 1-b-δ-Ribosyl-3-pyridinecarboxamide 1-beta-D-Ribosyl-3-Pyridinecarboxamide 1-beta-delta-Ribosyl-3-Pyridinecarboxamide 1-β-D-Ribosyl-3-pyridinecarboxamide 1-β-δ-Ribosyl-3-pyridinecarboxamide 3-(Aminocarbonyl)-1-b-D-ribofuranosyl-pyridinium 3-(Aminocarbonyl)-1-b-delta-ribofuranosyl-pyridinium 3-(Aminocarbonyl)-1-b-δ-ribofuranosyl-pyridinium 3-(Aminocarbonyl)-1-beta-D-ribofuranosyl-Pyridinium 3-(Aminocarbonyl)-1-beta-delta-ribofuranosyl-Pyridinium 3-(Aminocarbonyl)-1-β-D-ribofuranosyl-pyridinium 3-(Aminocarbonyl)-1-β-δ-ribofuranosyl-pyridinium <i>N</i>-ribosyl-nicotinamide N-Ribosyl-nicotinamide N-Ribosylnicotinamide Nicotinamide ribonucleoside Nicotinamide ribose Nicotinamide riboside Nicotinamide-b-riboside Nicotinamide-beta-riboside Nicotinamide-β-riboside Ribosylnicotinamide 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 Solid Cytoplasm Periplasm logp -2.27 ALOGPS logs -1.73 ALOGPS solubility 5.45e+00 g/l 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 Nicotinate and nicotinamide metabolism ec00760 NAD salvage Even though NAD molecules are not consumed during oxidation reactions, they have a relatively short half-life. For example, in E. coli the NAD+ half-life is 90 minutes. Once enzymatically degraded, the pyrimidine moiety of the molecule can be recouped via the NAD salvage cycles. This pathway is used for two purposes: it recycles the internally degraded NAD products nicotinamide D-ribonucleotide (also known as nicotinamide mononucleotide, or NMN) and nicotinamide, and it is used for the assimilation of exogenous NAD+. NAD reacts spontaneously with water resulting in the release of hydrogen ion, AMP and beta-nicotinamide D-ribonucleotide. This enzyme can either interact spontaneously with water resulting in the release of D-ribofuranose 5-phosphate, hydrogen ion and Nacinamide. On the other hand beta-nicotinamide D-ribonucleotide can also react with water through NMN amidohydrolase resulting in ammonium, and Nicotinate beta-D-ribonucleotide. Also it can interact with water spontaneously resulting in the release of phosphate resulting in a Nicotinamide riboside. Niacinamide interacts with water through a nicotinamidase resulting in a release of ammonium and nicotinic acid. This compound interacts with water and phosphoribosyl pyrophosphate through an ATP driven nicotinate phosphoribosyltransferase resulting in the release of ADP, pyrophosphate and phosphate and nicotinate beta-D-ribonucleotide. Nicotinamide riboside interacts with an ATP driven NadR DNA-binding transcriptional repressor and NMN adenylyltransferase (Escherichia coli) resulting in a ADP, hydrogen ion and beta-nicotinamide D-ribonucleotide. This compound interacts with ATP and hydrogen ion through NadR DNA-binding transcriptional repressor and NMN adenylyltransferase resulting in pyrophosphate and NAD. Nicotinate beta-D-ribonucleotide is adenylated through the interaction with ATP and a hydrogen ion through a nicotinate-mononucleotide adenylyltransferase resulting in pyrophosphate and Nicotinic acid adenine dinucleotide. Nicotinic acid adenine dinucleotide interacts with L-glutamine and water through an ATP driven NAD synthetase, NH3-dependent resulting in AMP, pyrophosphate, hydrogen ion, L-glutamic acid and NAD. PW000830 Metabolic 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 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::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 HMDB00855 439924 388956 C03150 15927 NICOTINAMIDE_RIBOSE NNR Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 Bieganowski, P., Brenner, C. (2004). "Discoveries of nicotinamide riboside as a nutrient and conserved NRK genes establish a Preiss-Handler independent route to NAD+ in fungi and humans." Cell 117:495-502. 15137942 Wall KA, Klis M, Kornet J, Coyle D, Ame JC, Jacobson MK, Slama JT: Inhibition of the intrinsic NAD+ glycohydrolase activity of CD38 by carbocyclic NAD analogues. 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Bioorganic & Medicinal Chemistry Letters (2004), 1 Protein ushA P07024 USHA_ECOLI ushA http://ecmdb.ca/proteins/P07024.xml Multifunctional protein surE P0A840 SURE_ECOLI surE http://ecmdb.ca/proteins/P0A840.xml 5'-nucleotidase yjjG P0A8Y1 YJJG_ECOLI yjjG http://ecmdb.ca/proteins/P0A8Y1.xml Purine nucleoside phosphorylase deoD-type P0ABP8 DEOD_ECOLI deoD http://ecmdb.ca/proteins/P0ABP8.xml Transcriptional regulator nadR P27278 NADR_ECOLI nadR http://ecmdb.ca/proteins/P27278.xml 5'-nucleotidase yfbR P76491 YFBR_ECOLI yfbR http://ecmdb.ca/proteins/P76491.xml Nicotinamide riboside transporter pnuC P0AFK2 PNUC_ECOLI pnuC http://ecmdb.ca/proteins/P0AFK2.xml Nicotinamide riboside + Phosphate <> Niacinamide + alpha-D-Ribose 1-phosphate R02294 Nicotinamide ribotide + Water <> Nicotinamide riboside + Phosphate R02323 Nicotinamide riboside + Adenosine triphosphate > Hydrogen ion + Nicotinamide ribotide + ADP RIBOSYLNICOTINAMIDE-KINASE-RXN Adenosine triphosphate + Nicotinamide riboside > ADP + NMN Nicotinamide riboside + Adenosine triphosphate > Adenosine diphosphate + Hydrogen ion + beta-nicotinamide D-ribonucleotide + ADP + NMN PW_R003022