2.0 2012-05-31 13:53:23 -0600 2015-09-13 12:56:11 -0600 ECMDB01488 M2MDB000399 Nicotinic acid Nicotinic acid, also known as niacin or vitamin B3, is a derivative of pyridine, with a carboxyl group (COOH) at the 3-position. Other forms of vitamin B3 include the corresponding amide, nicotinamide ("niacinamide"), where the carboxyl group has been replaced by a carboxamide group (CONH2), as well as more complex amides and a variety of esters. The uptake of nicotinic acid by Escherichia coli is dependent on the presence of the enzyme nicotinic acid phosphoribosyl transferase and a source of energy. 3-Carboxylpyridine 3-Carboxypyridine 3-Pyridinecarboxylate 3-Pyridinecarboxylic acid 3-Pyridylcarboxylate 3-Pyridylcarboxylic acid Akotin Apelagrin Daskil Efacin Enduracin Linic Niac Niacin Niacine Niacor Nicacid Nicamin Nicangin Nico-400- Nico-Span Nicobid Nicocap Nicodelmine Nicolar Niconacid Nicosan 3 Nicotinate Nicotinic acid Nicotinipca Nicyl Nyclin Pellagrin Pelonin Slo-niacin Vitamin B3 Vitamin B₃ Wampocap C6H5NO2 123.1094 123.032028409 pyridine-3-carboxylic acid niacin 59-67-6 OC(=O)C1=CN=CC=C1 InChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9) PVNIIMVLHYAWGP-UHFFFAOYSA-N Solid Cytosol Extra-organism Periplasm logp 0.29 ALOGPS logs -0.17 ALOGPS solubility 8.31e+01 g/l ALOGPS melting_point 236.6 oC logp -0.17 ChemAxon pka_strongest_acidic 2.79 ChemAxon pka_strongest_basic 4.19 ChemAxon iupac pyridine-3-carboxylic acid ChemAxon average_mass 123.1094 ChemAxon mono_mass 123.032028409 ChemAxon smiles OC(=O)C1=CN=CC=C1 ChemAxon formula C6H5NO2 ChemAxon inchi InChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9) ChemAxon inchikey PVNIIMVLHYAWGP-UHFFFAOYSA-N ChemAxon polar_surface_area 50.19 ChemAxon refractivity 31.16 ChemAxon polarizability 11.3 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Porphyrin and chlorophyll metabolism ec00860 Nicotinate and nicotinamide metabolism ec00760 Riboflavin metabolism ec00740 Metabolic pathways eco01100 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 adenosylcobalamin salvage from cobinamide Cobinamide 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 B12 PW001884 Metabolic NAD salvage pathway I PYRIDNUCSAL-PWY adenosylcobalamin salvage from cobinamide I COBALSYN-PWY-1 Specdb::CMs 754 Specdb::CMs 755 Specdb::CMs 756 Specdb::CMs 757 Specdb::CMs 1037 Specdb::CMs 2756 Specdb::CMs 27987 Specdb::CMs 30223 Specdb::CMs 30321 Specdb::CMs 30648 Specdb::CMs 30893 Specdb::CMs 31339 Specdb::CMs 32373 Specdb::CMs 38091 Specdb::CMs 132627 Specdb::CMs 140361 Specdb::EiMs 446 Specdb::NmrOneD 1716 Specdb::NmrOneD 2514 Specdb::NmrOneD 3213 Specdb::NmrOneD 4801 Specdb::NmrOneD 4802 Specdb::NmrOneD 147860 Specdb::NmrOneD 147861 Specdb::NmrOneD 147862 Specdb::NmrOneD 147863 Specdb::NmrOneD 147864 Specdb::NmrOneD 147865 Specdb::NmrOneD 147866 Specdb::NmrOneD 147867 Specdb::NmrOneD 147868 Specdb::NmrOneD 147869 Specdb::NmrOneD 147870 Specdb::NmrOneD 147871 Specdb::NmrOneD 147872 Specdb::NmrOneD 147873 Specdb::NmrOneD 147874 Specdb::NmrOneD 147875 Specdb::NmrOneD 147876 Specdb::NmrOneD 147877 Specdb::NmrOneD 147878 Specdb::NmrOneD 147879 Specdb::MsMs 1604 Specdb::MsMs 1605 Specdb::MsMs 1606 Specdb::MsMs 5336 Specdb::MsMs 5337 Specdb::MsMs 5338 Specdb::MsMs 5339 Specdb::MsMs 5340 Specdb::MsMs 5341 Specdb::MsMs 5342 Specdb::MsMs 5343 Specdb::MsMs 5344 Specdb::MsMs 5345 Specdb::MsMs 5346 Specdb::MsMs 5351 Specdb::MsMs 5352 Specdb::MsMs 5353 Specdb::MsMs 178800 Specdb::MsMs 178801 Specdb::MsMs 178802 Specdb::MsMs 181119 Specdb::MsMs 181120 Specdb::MsMs 181121 Specdb::MsMs 438191 Specdb::MsMs 438192 Specdb::NmrTwoD 1075 Specdb::NmrTwoD 1656 HMDB01488 938 913 C00253 15940 NIACINE NIO Nicotinic acid Keseler, I. 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Journal of the American Chemical Society (1941), 63 2283-4. http://hmdb.ca/system/metabolites/msds/000/001/350/original/HMDB01488.pdf?1358461732 Purine nucleoside phosphorylase deoD-type P0ABP8 DEOD_ECOLI deoD http://ecmdb.ca/proteins/P0ABP8.xml Nicotinate phosphoribosyltransferase P18133 PNCB_ECOLI pncB http://ecmdb.ca/proteins/P18133.xml Pyrazinamidase/nicotinamidase P21369 PNCA_ECOLI pncA http://ecmdb.ca/proteins/P21369.xml Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase P36562 COBT_ECOLI cobT http://ecmdb.ca/proteins/P36562.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Adenosine triphosphate + Water + Nicotinic acid + Phosphoribosyl pyrophosphate > ADP + Nicotinamide ribotide + Phosphate + Pyrophosphate Water + Niacinamide > Nicotinic acid + Ammonium Dimethylbenzimidazole + Nicotinamide ribotide <> N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole + Hydrogen ion + Nicotinic acid R04148 DMBPPRIBOSYLTRANS-RXN Niacinamide + Water <> Nicotinic acid + Ammonia R01268 Nicotinamide ribotide + Pyrophosphate + Adenosine triphosphate + Water <> Nicotinic acid + Phosphoribosyl pyrophosphate + ADP + Phosphate R01724 Nicotinate D-ribonucleoside + Phosphate <> Nicotinic acid + alpha-D-Ribose 1-phosphate + Hydrogen ion R02295 Nicotinamide ribotide + Dimethylbenzimidazole > Hydrogen ion + Nicotinic acid + N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole DMBPPRIBOSYLTRANS-RXN Niacinamide + Water > Hydrogen ion + Nicotinic acid + Ammonia R01268 NICOTINAMID-RXN Nicotinamide ribotide + Pyrophosphate < Hydrogen ion + Nicotinic acid + Phosphoribosyl pyrophosphate R01724 NICOTINATEPRIBOSYLTRANS-RXN Nicotinamide ribotide + Dimethylbenzimidazole > Nicotinic acid + N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole Niacinamide + Water > Nicotinic acid + Ammonia R01268 NICOTINAMID-RXN Nicotinamide ribotide + Pyrophosphate > Nicotinic acid + Phosphoribosyl pyrophosphate R01724 NICOTINATEPRIBOSYLTRANS-RXN Nicotinic acid + Water + Adenosine triphosphate + Phosphoribosyl pyrophosphate > Phosphate + Adenosine diphosphate + Pyrophosphate + nicotinate beta-D-ribonucleotide + ADP + Nicotinamide ribotide PW_R003016 Dimethylbenzimidazole + nicotinate beta-D-ribonucleotide + Nicotinamide ribotide > Hydrogen ion + Nicotinic acid + N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole PW_R005142 Nicotinamide ribotide + Pyrophosphate + Adenosine triphosphate + Water <> Nicotinic acid + Phosphoribosyl pyrophosphate + ADP + Phosphate Nicotinamide ribotide + Pyrophosphate + Adenosine triphosphate + Water <> Nicotinic acid + Phosphoribosyl pyrophosphate + ADP + Phosphate