2.02012-05-31 10:24:17 -06002015-09-13 12:56:07 -0600ECMDB00229M2MDB000095Nicotinamide ribotideNicotinamide ribotide (NMN) is an important intermediate metabolite in the nicotinate and nicotinamide metabolism pathway. Nicotinamide is directly converted to NMN by nicotinamide phosphoribosyltransferase (NAMPT, EC 2.4.2.12). The enzyme nicotinamide mononucleotide adenylyltransferase (NMNAT, EC 2.7.7.1), a member of the nucleotidyltransferase alpha/beta-phosphodiesterase superfamily, catalyzes the reaction NMN + ATP = Nicotinamide adenine dinucleotide (NAD) + PPi, representing the final step in the biosynthesis of NAD, a molecule playing a fundamental role as a cofactor in cellular redox reactions. Thus NMN is an important metabolite for the maintenance of normal NAD biosynthesis, and circulating NMN levels may play an important role in regulating cell function in physiological and pathophysiological conditions. (PMID: 15078171, 17983582)β-nicotinamide mononucleotideβ-nicotinamide nucleotideβ-nicotinamide ribonucleotide3-(Aminocarbonyl)-1-(5-O-phosphono-b-D-ribofuranosyl)-Pyridinium hydroxide inner salt3-(Aminocarbonyl)-1-(5-O-phosphono-b-D-ribofuranosyl)-Pyridinium inner salt3-(Aminocarbonyl)-1-(5-O-phosphono-b-delta-ribofuranosyl)-pyridinium hydroxide inner salt3-(Aminocarbonyl)-1-(5-O-phosphono-b-delta-ribofuranosyl)-pyridinium inner salt3-(Aminocarbonyl)-1-(5-O-phosphono-b-δ-ribofuranosyl)-pyridinium hydroxide inner salt3-(Aminocarbonyl)-1-(5-O-phosphono-b-δ-ribofuranosyl)-pyridinium inner salt3-(Aminocarbonyl)-1-(5-O-phosphono-beta-delta-ribofuranosyl)-Pyridinium hydroxide inner salt3-(Aminocarbonyl)-1-(5-O-phosphono-beta-delta-ribofuranosyl)-Pyridinium inner salt3-(Aminocarbonyl)-1-(5-O-phosphono-β-δ-ribofuranosyl)-pyridinium hydroxide inner salt3-(Aminocarbonyl)-1-(5-O-phosphono-β-δ-ribofuranosyl)-pyridinium inner salt3-Carbamoyl-1-b-D-ribofuranosylpyridinium hydroxide 5'-phosphate inner salt3-Carbamoyl-1-b-D-ribofuranosylpyridinium hydroxide 5'-phosphoric acid inner salt3-Carbamoyl-1-b-delta-ribofuranosylpyridinium hydroxide 5'-phosphate inner salt3-Carbamoyl-1-b-delta-ribofuranosylpyridinium hydroxide 5'-phosphoric acid inner salt3-Carbamoyl-1-b-δ-ribofuranosylpyridinium hydroxide 5'-phosphate inner salt3-Carbamoyl-1-b-δ-ribofuranosylpyridinium hydroxide 5'-phosphoric acid inner salt3-Carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-phosphate inner salt3-Carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-phosphoric acid inner salt3-Carbamoyl-1-β-δ-ribofuranosylpyridinium hydroxide 5'-phosphate inner salt3-Carbamoyl-1-β-δ-ribofuranosylpyridinium hydroxide 5'-phosphoric acid inner salt3-Carboxy-1-(5-O-phosphono-b-D-ribofuranosyl)-Pyridinium inner salt3-Carboxy-1-(5-O-phosphono-b-delta-ribofuranosyl)-pyridinium inner salt3-Carboxy-1-(5-O-phosphono-b-δ-ribofuranosyl)-pyridinium inner salt3-Carboxy-1-(5-O-phosphono-beta-D-ribofuranosyl)-Pyridinium inner salt3-Carboxy-1-(5-O-phosphono-beta-delta-ribofuranosyl)-Pyridinium inner salt3-Carboxy-1-(5-O-phosphono-β-D-ribofuranosyl)-pyridinium inner salt3-Carboxy-1-(5-O-phosphono-β-δ-ribofuranosyl)-pyridinium inner salt3-Carboxy-1-b-D-ribofuranosylpyridinium hydroxide 5'-phosphate inner salt3-Carboxy-1-b-D-ribofuranosylpyridinium hydroxide 5'-phosphoric acid inner salt3-Carboxy-1-b-delta-ribofuranosylpyridinium hydroxide 5'-phosphate inner salt3-Carboxy-1-b-delta-ribofuranosylpyridinium hydroxide 5'-phosphoric acid inner salt3-Carboxy-1-b-δ-ribofuranosylpyridinium hydroxide 5'-phosphate inner salt3-Carboxy-1-b-δ-ribofuranosylpyridinium hydroxide 5'-phosphoric acid inner salt3-Carboxy-1-beta-D-ribofuranosylpyridinium hydroxide 5'-phosphate inner salt3-Carboxy-1-beta-D-ribofuranosylpyridinium hydroxide 5'-phosphoric acid inner salt3-Carboxy-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-phosphate inner salt3-Carboxy-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-phosphoric acid inner salt3-Carboxy-1-β-D-ribofuranosylpyridinium hydroxide 5'-phosphate inner salt3-Carboxy-1-β-D-ribofuranosylpyridinium hydroxide 5'-phosphoric acid inner salt3-Carboxy-1-β-δ-ribofuranosylpyridinium hydroxide 5'-phosphate inner salt3-Carboxy-1-β-δ-ribofuranosylpyridinium hydroxide 5'-phosphoric acid inner salt3-Pyridinecarboxylate mononucleotide3-Pyridinecarboxylic acid mononucleotideB-D-NMNb-delta-NMNb-Nicotinamide mononucleotideb-Nicotinamide nucleotideb-Nicotinamide ribonucleotideb-Nicotinamide-D-ribonucleotideb-Nicotinate D-ribonucleotideb-Nicotinate mononucleotideb-Nicotinate-D-nucleotideb-Nicotinic acid D-ribonucleotideb-Nicotinic acid mononucleotideb-Nicotinic acid-D-nucleotideB-NMNb-δ-NMNBeta-delta-NMNBeta-Nicotinamide mononucleotideBeta-Nicotinamide nucleotideBeta-Nicotinamide ribonucleotideBeta-Nicotinamide-D-ribonucleotideBeta-Nicotinate D-ribonucleotideBeta-Nicotinate mononucleotideBeta-Nicotinate-D-nucleotideBeta-Nicotinic acid D-ribonucleotideBeta-Nicotinic acid mononucleotidebeta-Nicotinic acid-D-nucleotideBeta-NMNDeamido nicotinamide ribonucleotideDeamido-nicotinamide mononucleotideDeamido-NMNNaMNNicotinamide D-ribonucleotideNicotinamide mononucleotideNicotinamide ribonucleoside 5'-phosphateNicotinamide ribonucleoside 5'-phosphoric acidNicotinamide ribonucleotideNicotinate D-ribonucleosideNicotinate D-ribonucleotideNicotinate dinucleotideNicotinate mononucleotideNicotinate nucleotideNicotinate ribonucleotideNicotinate ribotideNicotinate-D-ribonucleotideNicotinate-delta-ribonucleotideNicotinate-δ-ribonucleotideNicotinic acid D-ribonucleosideNicotinic acid D-ribonucleotideNicotinic acid dinucleotideNicotinic acid mononucleotideNicotinic acid nucleotideNicotinic acid ribonucleotideNicotinic acid ribotideNicotinic acid-D-ribonucleotideNicotinic acid-delta-ribonucleotideNicotinic acid-δ-ribonucleotideNicotinic mononucleotideNMNβ-Nicotinamide mononucleotideβ-Nicotinamide nucleotideβ-Nicotinamide ribonucleotideβ-Nicotinamide-D-ribonucleotideβ-Nicotinate D-ribonucleotideβ-Nicotinate mononucleotideβ-Nicotinate-D-nucleotideβ-Nicotinic acid D-ribonucleotideβ-Nicotinic acid mononucleotideβ-Nicotinic acid-D-nucleotideβ-NMNβ-δ-NMNC11H15NO9P336.2119336.0484425953-carboxy-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1lambda5-pyridin-1-ylium3-carboxy-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1lambda5-pyridin-1-ylium1094-61-7O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)[N+]1=CC=CC(=C1)C(O)=OInChI=1S/C11H14NO9P/c13-8-7(5-20-22(17,18)19)21-10(9(8)14)12-3-1-2-6(4-12)11(15)16/h1-4,7-10,13-14H,5H2,(H2-,15,16,17,18,19)/p+1/t7-,8-,9-,10-/m1/s1JOUIQRNQJGXQDC-ZYUZMQFOSA-OSolidCytosolExtra-organismPeriplasmlogp-0.99logs-2.34solubility1.71e+00 g/llogp-5.4pka_strongest_acidic1.2pka_strongest_basic-3.7iupac3-carboxy-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1lambda5-pyridin-1-yliumaverage_mass336.2119mono_mass336.048442595smilesO[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)[N+]1=CC=CC(=C1)C(O)=OformulaC11H15NO9PinchiInChI=1S/C11H14NO9P/c13-8-7(5-20-22(17,18)19)21-10(9(8)14)12-3-1-2-6(4-12)11(15)16/h1-4,7-10,13-14H,5H2,(H2-,15,16,17,18,19)/p+1/t7-,8-,9-,10-/m1/s1inchikeyJOUIQRNQJGXQDC-ZYUZMQFOSA-Opolar_surface_area157.63refractivity69.89polarizability28.66rotatable_bond_count5acceptor_count8donor_count5physiological_charge-2formal_charge1Porphyrin and chlorophyll metabolismec00860Nicotinate and nicotinamide metabolismec00760Riboflavin metabolismec00740Metabolic pathwayseco01100NAD biosynthesisNicotinamide adenine dinucleotide (NAD) can be biosynthesized from L-aspartic acid.This amino acid reacts with oxygen through an L-aspartate oxidase resulting in a hydrogen ion, hydrogen peroxide and an iminoaspartic acid. The latter compound interacts with dihydroxyacetone phosphate through a quinolinate synthase A, resulting in a phosphate, water, and a quinolic acid. Quinolic acid interacts with phosphoribosyl pyrophosphate and hydrogen ion through a quinolinate phosphoribosyltransferase resulting in pyrophosphate, carbon dioxide and nicotinate beta-D-ribonucleotide. This last compound is adenylated through an ATP driven nicotinate-mononucleotide adenylyltransferase releasing a pyrophosphate and resulting in a nicotinic acid adenine dinucleotide.
Nicotinic acid adenine dinucleotide is processed through an NAD synthetase, NH3-dependent in two different manners.
In the first case, Nicotinic acid adenine dinucleotide interacts with ATP, L-glutamine and water through the enzyme and results in hydrogen ion, AMP, pyrophosphate, L-glutamic acid and NAD.
In the second case, Nicotinic acid adenine dinucleotide interacts with ATP and ammonium through the enzyme resulting in a pyrophosphate, AMP, hydrogen ion and NAD.
NAD then proceeds to regulate its own pathway by repressing L-aspartate oxidase.
As a general rule, most prokaryotes utilize the aspartate de novo pathway, in which the nicotinate moiety of NAD is synthesized from aspartate , while in eukaryotes, the de novo pathway starts with tryptophan.
PW000829MetabolicNAD salvageEven 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.
PW000830Metabolicadenosylcobalamin salvage from cobinamideCobinamide is incorporated from the extracellular space through a transport system into the cytosol. Once inside the cytosol, cobinamide interacts with ATP through a cobinamide adenosyl transferase resulting in the release of a triphosphate and an adenosylcobinamide. The latter compound is then phosphorylated through an ATP-dependent cobinamide kinase resulting in the release of ADP, a hydrogen ion and adenosyl-cobinamide phosphate. This last compound then interacts with GTP and a hydrogen ion through a cobinamide-P guanylyltransferase resulting in the release of a pyrophosphate and an adenosylcobinamide-GDP.
A dimethylbenzimidazole interacts with a nicotinate D-ribonucleotide through a nicotinate-nucleotide dimethylbenzumidazole phosphoribosyltransferase resulting in the release of a nicotinate, a hydrogen ion and an alpha-ribazole 5' phosphate.
The adenosylcobinamide-GDP and the alpha-ribazole 5' phosphate interact together through a cobalamin 5' phosphate synthase resulting in the release of a hydrogen ion, a GMP and Adenosylcobalamin 5'-phosphate. The latter compound then interacts with a water molecule through an adenosylcbalamin 5' phosphate phosphatase resulting in the release of a phosphate and a coenzyme B12.
Likewise a cobalamin molecule can interact with ATP through a cobalamin adenosyltransferase resulting in the release of a triphosphate and a coenzyme B12PW001884MetabolicNAD salvage pathway IPYRIDNUCSAL-PWYNAD biosynthesis I (from aspartate)PYRIDNUCSYN-PWYadenosylcobalamin salvage from cobinamide ICOBALSYN-PWY-1Specdb::CMs2925Specdb::CMs47837Specdb::CMs154102Specdb::NmrOneD8722Specdb::NmrOneD8723Specdb::NmrOneD8724Specdb::NmrOneD8725Specdb::NmrOneD8726Specdb::NmrOneD8727Specdb::NmrOneD8728Specdb::NmrOneD8729Specdb::NmrOneD8730Specdb::NmrOneD8731Specdb::NmrOneD8732Specdb::NmrOneD8733Specdb::NmrOneD8734Specdb::NmrOneD8735Specdb::NmrOneD8736Specdb::NmrOneD8737Specdb::NmrOneD8738Specdb::NmrOneD8739Specdb::NmrOneD8740Specdb::NmrOneD8741Specdb::MsMs27119Specdb::MsMs27120Specdb::MsMs27121Specdb::MsMs33677Specdb::MsMs33678Specdb::MsMs33679Specdb::MsMs2520494Specdb::MsMs2520495Specdb::MsMs2520496HMDB002291418013553C0118516171NICOTINAMIDE_NUCLEOTIDENCNKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25.17765195Magni, G., Amici, A., Emanuelli, M., Orsomando, G., Raffaelli, N., Ruggieri, S. (2004). "Structure and function of nicotinamide mononucleotide adenylyltransferase." Curr Med Chem 11:873-885.15078171Liu, Rihe; Visscher, Johannes. A novel preparation of nicotinamide mononucleotide. Nucleosides & Nucleotides (1994), 13(5), 1215-16.http://hmdb.ca/system/metabolites/msds/000/000/166/original/HMDB00229.pdf?1358463254Protein ushAP07024USHA_ECOLIushAhttp://ecmdb.ca/proteins/P07024.xmlNicotinate-nucleotide adenylyltransferaseP0A752NADD_ECOLInadDhttp://ecmdb.ca/proteins/P0A752.xmlMultifunctional protein surEP0A840SURE_ECOLIsurEhttp://ecmdb.ca/proteins/P0A840.xml5'-nucleotidase yjjGP0A8Y1YJJG_ECOLIyjjGhttp://ecmdb.ca/proteins/P0A8Y1.xmlDNA ligaseP15042DNLJ_ECOLIligAhttp://ecmdb.ca/proteins/P15042.xmlNicotinate phosphoribosyltransferaseP18133PNCB_ECOLIpncBhttp://ecmdb.ca/proteins/P18133.xmlDNA ligase BP25772LIGB_ECOLIligBhttp://ecmdb.ca/proteins/P25772.xmlTranscriptional regulator nadRP27278NADR_ECOLInadRhttp://ecmdb.ca/proteins/P27278.xmlNicotinate-nucleotide pyrophosphorylase [carboxylating]P30011NADC_ECOLInadChttp://ecmdb.ca/proteins/P30011.xmlNADH pyrophosphataseP32664NUDC_ECOLInudChttp://ecmdb.ca/proteins/P32664.xmlNicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferaseP36562COBT_ECOLIcobThttp://ecmdb.ca/proteins/P36562.xml5'-nucleotidase yfbRP76491YFBR_ECOLIyfbRhttp://ecmdb.ca/proteins/P76491.xmlNicotinamide-nucleotide amidohydrolase PncCP0A6G3PNCC_ECOLIpncChttp://ecmdb.ca/proteins/P0A6G3.xmlNicotinamide riboside transporter pnuCP0AFK2PNUC_ECOLIpnuChttp://ecmdb.ca/proteins/P0AFK2.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlWater + NAD <> Adenosine monophosphate +2 Hydrogen ion + Nicotinamide ribotide + NMNR00103NADPYROPHOSPHAT-RXNAdenosine triphosphate + Hydrogen ion + Nicotinamide ribotide + NMN <> NAD + PyrophosphateR001372.7.7.1-RXN2 Hydrogen ion + Phosphoribosyl pyrophosphate + Quinolinic acid <> Carbon dioxide + Nicotinamide ribotide + PyrophosphateR03348QUINOPRIBOTRANS-RXNAdenosine triphosphate + Hydrogen ion + Nicotinamide ribotide <> Nicotinic acid adenine dinucleotide + PyrophosphateR03005NICONUCADENYLYLTRAN-RXNAdenosine triphosphate + Water + Nicotinic acid + Phosphoribosyl pyrophosphate > ADP + Nicotinamide ribotide + Phosphate + PyrophosphateDimethylbenzimidazole + Nicotinamide ribotide <> N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole + Hydrogen ion + Nicotinic acidR04148DMBPPRIBOSYLTRANS-RXNNAD + Water <> Adenosine monophosphate + Nicotinamide ribotideR00103NADPYROPHOSPHAT-RXNAdenosine triphosphate + Nicotinamide ribotide <> Pyrophosphate + NADR001372.7.7.1-RXNNicotinamide ribotide + Pyrophosphate + Adenosine triphosphate + Water <> Nicotinic acid + Phosphoribosyl pyrophosphate + ADP + PhosphateR01724Nicotinamide ribotide + Water <> Nicotinamide riboside + PhosphateR02323Nicotinic acid adenine dinucleotide + Water <> Adenosine monophosphate + Nicotinamide ribotideR03004Adenosine triphosphate + Nicotinamide ribotide <> Pyrophosphate + Nicotinic acid adenine dinucleotideR03005Nicotinamide ribotide + Water <> Nicotinate D-ribonucleoside + PhosphateR03346Nicotinamide ribotide + Pyrophosphate + Carbon dioxide <> Quinolinic acid + Phosphoribosyl pyrophosphateR03348Hydrogen ion + Nicotinamide ribotide + Adenosine triphosphate <> NAD + Pyrophosphate2.7.7.1-RXNNicotinamide ribotide + Dimethylbenzimidazole > Hydrogen ion + Nicotinic acid + N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazoleDMBPPRIBOSYLTRANS-RXNDNA<sub><i>n</i></sub> + (deoxynucleotides)<sub>(m)</sub> + NAD > (deoxynucleotides)<sub>(m)</sub> + Nicotinamide ribotide + Adenosine monophosphateDNA-LIGASE-NAD+-RXNWater + NAD > Hydrogen ion + Nicotinamide ribotide + Adenosine monophosphateNADPYROPHOSPHAT-RXNHydrogen ion + Adenosine triphosphate + Nicotinamide ribotide > Pyrophosphate + Nicotinic acid adenine dinucleotideNICONUCADENYLYLTRAN-RXNNicotinamide ribotide + Pyrophosphate < Hydrogen ion + Nicotinic acid + Phosphoribosyl pyrophosphateR01724NICOTINATEPRIBOSYLTRANS-RXNNicotinamide ribotide + Water > Hydrogen ion + Nicotinamide ribotide + AmmoniaNMNAMIDOHYDRO-RXNNicotinamide ribotide + Water > Hydrogen ion + Nicotinamide ribotide + AmmoniaNMNAMIDOHYDRO-RXNWater + Nicotinamide ribotide <> Hydrogen ion + D-Ribose-5-phosphate + NiacinamideNMNNUCLEOSID-RXNNicotinamide ribotide + Pyrophosphate + Carbon dioxide < Phosphoribosyl pyrophosphate + Quinolinic acid + Hydrogen ionQUINOPRIBOTRANS-RXNNicotinamide riboside + Adenosine triphosphate > Hydrogen ion + Nicotinamide ribotide + ADPRIBOSYLNICOTINAMIDE-KINASE-RXNNicotinamide ribotide + Dimethylbenzimidazole > Nicotinic acid + N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazoleNicotinamide ribotide + Pyrophosphate + Carbon dioxide > Quinolinic acid + Phosphoribosyl pyrophosphateAdenosine triphosphate + Nicotinamide ribotide > Pyrophosphate + Nicotinic acid adenine dinucleotideNicotinamide ribotide + Pyrophosphate > Nicotinic acid + Phosphoribosyl pyrophosphateR01724NICOTINATEPRIBOSYLTRANS-RXNNMN + Water <> Nicotinamide ribotide + AmmoniaR02322 Quinolinic acid + Hydrogen ion + Phosphoribosyl pyrophosphate > Carbon dioxide + Pyrophosphate + nicotinate beta-D-ribonucleotide + Nicotinamide ribotidePW_R003009nicotinate beta-D-ribonucleotide + Adenosine triphosphate + Hydrogen ion + Nicotinamide ribotide > Pyrophosphate + Nicotinic acid adenine dinucleotidePW_R003010Nicotinic acid + Water + Adenosine triphosphate + Phosphoribosyl pyrophosphate > Phosphate + Adenosine diphosphate + Pyrophosphate + nicotinate beta-D-ribonucleotide + ADP + Nicotinamide ribotidePW_R003016beta-nicotinamide D-ribonucleotide + Water + NMN > Ammonium + nicotinate beta-D-ribonucleotide + Nicotinamide ribotidePW_R003017Dimethylbenzimidazole + nicotinate beta-D-ribonucleotide + Nicotinamide ribotide > Hydrogen ion + Nicotinic acid + N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazolePW_R005142Water + NAD <> Adenosine monophosphate +2 Hydrogen ion + Nicotinamide ribotide + NMNNAD + Water <> Adenosine monophosphate + Nicotinamide ribotideNMN + Water <> Nicotinamide ribotide + AmmoniaAdenosine triphosphate + Hydrogen ion + Nicotinamide ribotide + NMN <> NAD + Pyrophosphate2 Hydrogen ion + Phosphoribosyl pyrophosphate + Quinolinic acid <> Carbon dioxide + Nicotinamide ribotide + PyrophosphateNicotinamide ribotide + Pyrophosphate + Adenosine triphosphate + Water <> Nicotinic acid + Phosphoribosyl pyrophosphate + ADP + PhosphateWater + NAD <> Adenosine monophosphate +2 Hydrogen ion + Nicotinamide ribotide + NMN2 Hydrogen ion + Phosphoribosyl pyrophosphate + Quinolinic acid <> Carbon dioxide + Nicotinamide ribotide + PyrophosphateNicotinamide ribotide + Pyrophosphate + Adenosine triphosphate + Water <> Nicotinic acid + Phosphoribosyl pyrophosphate + ADP + Phosphate