2.0 2012-05-31 13:51:56 -0600 2015-09-13 12:56:11 -0600 ECMDB01406 M2MDB000374 Niacinamide Nicotinamide, also known as niacinamide and nicotinic acid amide, is the amide of nicotinic acid (vitamin B3). Nicotinamide is a water-soluble vitamin and is part of the vitamin B group. In cells, niacin is incorporated into nicotinamide adenine dinucleotide (NAD) and nicotinamide adenine dinucleotide phosphate (NADP), although the pathways for nicotinamide and nicotinic acid are very similar. NAD+ and NADP+ are coenzymes in a wide variety of enzymatic oxidation-reduction reactions. (Wikipedia) 3-Carbamoylpyridine 3-Pyridinecarboxamide 3-Pyridinecarboxylate amide 3-Pyridinecarboxylic acid amide 6-Aminonicotinamide Acid amide Amid kyseliny nikotinove Amide PP Aminicotin Amixicotyn Amnicotin Austrovit PP B-Pyridinecarboxamide Benicot Beta-Pyridinecarboxamide Delonin Amide Dipegyl Dipigyl Endobion Factor pp Hansamid Inovitan PP M-(Aminocarbonyl)pyridine Mediatric NAM Nandervit-N Niacevit Niacinamide Niamide Niavit PP Nicamide Nicamina Nicamindon Nicasir Nicobion Nicofort Nicogen Nicomidol Nicosan 2 Nicosylamide Nicota Nicotamide Nicotilamide Nicotililamido Nicotinamida Nicotinamide Nicotinamidum Nicotinate amide Nicotine acid amide Nicotine amide Nicotinic acid amide Nicotinic amide Nicotinsaureamid Nicotol Nicotylamide Nicotylamidum Nicovel Nicovit Nicovitina Nicovitol Nicozymin Nictoamide Niko-tamin Nikotinamid Nikotinsaeureamid Niocinamide Niozymin Papulex Pelmin Pelmine Pelonin amide PP-Faktor Propamine A Pyridine-3-carboxylate amide Pyridine-3-carboxylic acid amide Savacotyl Vi-Nicotyl Vi-noctyl Vitamin B3 Vitamin PP Witamina PP β-Pyridinecarboxamide C6H6N2O 122.1246 122.048012824 pyridine-3-carboxamide nicotinamide 98-92-0 NC(=O)C1=CC=CN=C1 InChI=1S/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9) DFPAKSUCGFBDDF-UHFFFAOYSA-N Solid Cytosol logp -0.45 ALOGPS logs -0.39 ALOGPS solubility 5.01e+01 g/l ALOGPS melting_point 130 oC logp -0.39 ChemAxon pka_strongest_acidic 13.39 ChemAxon pka_strongest_basic 3.63 ChemAxon iupac pyridine-3-carboxamide ChemAxon average_mass 122.1246 ChemAxon mono_mass 122.048012824 ChemAxon smiles NC(=O)C1=CC=CN=C1 ChemAxon formula C6H6N2O ChemAxon inchi InChI=1S/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9) ChemAxon inchikey DFPAKSUCGFBDDF-UHFFFAOYSA-N ChemAxon polar_surface_area 55.98 ChemAxon refractivity 32.98 ChemAxon polarizability 11.71 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Nicotinate and nicotinamide metabolism ec00760 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 NAD salvage pathway I PYRIDNUCSAL-PWY Specdb::CMs 743 Specdb::CMs 744 Specdb::CMs 745 Specdb::CMs 1161 Specdb::CMs 1185 Specdb::CMs 3187 Specdb::CMs 27986 Specdb::CMs 29777 Specdb::CMs 30122 Specdb::CMs 30222 Specdb::CMs 30647 Specdb::CMs 30890 Specdb::CMs 31328 Specdb::CMs 31329 Specdb::CMs 31946 Specdb::CMs 131871 Specdb::CMs 139605 Specdb::EiMs 1017 Specdb::NmrOneD 1299 Specdb::NmrOneD 1700 Specdb::NmrOneD 2742 Specdb::NmrOneD 3436 Specdb::NmrOneD 4818 Specdb::NmrOneD 4819 Specdb::NmrOneD 95938 Specdb::NmrOneD 95939 Specdb::NmrOneD 95940 Specdb::NmrOneD 95941 Specdb::NmrOneD 95942 Specdb::NmrOneD 95943 Specdb::NmrOneD 95944 Specdb::NmrOneD 95945 Specdb::NmrOneD 95946 Specdb::NmrOneD 95947 Specdb::NmrOneD 95948 Specdb::NmrOneD 95949 Specdb::NmrOneD 95950 Specdb::NmrOneD 95951 Specdb::NmrOneD 95952 Specdb::NmrOneD 95953 Specdb::NmrOneD 95954 Specdb::NmrOneD 95955 Specdb::NmrOneD 95956 Specdb::MsMs 1559 Specdb::MsMs 1560 Specdb::MsMs 1561 Specdb::MsMs 5272 Specdb::MsMs 5273 Specdb::MsMs 5274 Specdb::MsMs 5275 Specdb::MsMs 5276 Specdb::MsMs 5277 Specdb::MsMs 5281 Specdb::MsMs 5282 Specdb::MsMs 5283 Specdb::MsMs 5284 Specdb::MsMs 20600 Specdb::MsMs 20601 Specdb::MsMs 20602 Specdb::MsMs 22151 Specdb::MsMs 22152 Specdb::MsMs 22153 Specdb::MsMs 446630 Specdb::MsMs 446631 Specdb::MsMs 446632 Specdb::MsMs 446633 Specdb::MsMs 446634 Specdb::MsMs 447320 Specdb::NmrTwoD 1068 Specdb::NmrTwoD 1641 HMDB01406 936 911 C00153 17154 NIACINAMIDE NCA Niacinamide Keseler, I. 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Journal of the American Chemical Society (1948), 70 3945. http://hmdb.ca/system/metabolites/msds/000/001/268/original/HMDB01406.pdf?1358462677 Purine nucleoside phosphorylase deoD-type P0ABP8 DEOD_ECOLI deoD http://ecmdb.ca/proteins/P0ABP8.xml Pyrazinamidase/nicotinamidase P21369 PNCA_ECOLI pncA http://ecmdb.ca/proteins/P21369.xml deacetylase of acs and cheY, regulates chemotaxis P75960 cobB http://ecmdb.ca/proteins/P75960.xml Water + Niacinamide > Nicotinic acid + Ammonium Niacinamide + Water <> Nicotinic acid + Ammonia R01268 Nicotinamide riboside + Phosphate <> Niacinamide + alpha-D-Ribose 1-phosphate R02294 Water + NAD <> Hydrogen ion + Adenosine diphosphate ribose + Niacinamide NADNUCLEOSID-RXN Niacinamide + Water > Hydrogen ion + Nicotinic acid + Ammonia R01268 NICOTINAMID-RXN Water + Nicotinamide ribotide <> Hydrogen ion + D-Ribose-5-phosphate + Niacinamide NMNNUCLEOSID-RXN NAD + an acetylprotein > Niacinamide + O-acetyl-ADP-ribose + a protein Niacinamide + Water > Nicotinic acid + Ammonia R01268 NICOTINAMID-RXN 48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L Gluco Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h 44.2 uM 0.0 37 oC BW25113 Stationary Phase, glucose limited 176800 0 Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. 17379776