2.02012-05-31 13:51:56 -06002015-09-13 12:56:11 -0600ECMDB01406M2MDB000374NiacinamideNicotinamide, 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-Carbamoylpyridine3-Pyridinecarboxamide3-Pyridinecarboxylate amide3-Pyridinecarboxylic acid amide6-AminonicotinamideAcid amideAmid kyseliny nikotinoveAmide PPAminicotinAmixicotynAmnicotinAustrovit PPB-PyridinecarboxamideBenicotBeta-PyridinecarboxamideDelonin AmideDipegylDipigylEndobionFactor ppHansamidInovitan PPM-(Aminocarbonyl)pyridineMediatricNAMNandervit-NNiacevitNiacinamideNiamideNiavit PPNicamideNicaminaNicamindonNicasirNicobionNicofortNicogenNicomidolNicosan 2NicosylamideNicotaNicotamideNicotilamideNicotililamidoNicotinamidaNicotinamideNicotinamidumNicotinate amideNicotine acid amideNicotine amideNicotinic acid amideNicotinic amideNicotinsaureamidNicotolNicotylamideNicotylamidumNicovelNicovitNicovitinaNicovitolNicozyminNictoamideNiko-taminNikotinamidNikotinsaeureamidNiocinamideNiozyminPapulexPelminPelminePelonin amidePP-FaktorPropamine APyridine-3-carboxylate amidePyridine-3-carboxylic acid amideSavacotylVi-NicotylVi-noctylVitamin B3Vitamin PPWitamina PPβ-PyridinecarboxamideC6H6N2O122.1246122.048012824pyridine-3-carboxamidenicotinamide98-92-0NC(=O)C1=CC=CN=C1InChI=1S/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9)DFPAKSUCGFBDDF-UHFFFAOYSA-NSolidCytosollogp-0.45logs-0.39solubility5.01e+01 g/lmelting_point130 oClogp-0.39pka_strongest_acidic13.39pka_strongest_basic3.63iupacpyridine-3-carboxamideaverage_mass122.1246mono_mass122.048012824smilesNC(=O)C1=CC=CN=C1formulaC6H6N2OinchiInChI=1S/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9)inchikeyDFPAKSUCGFBDDF-UHFFFAOYSA-Npolar_surface_area55.98refractivity32.98polarizability11.71rotatable_bond_count1acceptor_count2donor_count1physiological_charge0formal_charge0Nicotinate and nicotinamide metabolismec00760Metabolic pathwayseco01100NAD 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.
PW000830MetabolicNAD salvage pathway IPYRIDNUCSAL-PWYSpecdb::CMs743Specdb::CMs744Specdb::CMs745Specdb::CMs1161Specdb::CMs1185Specdb::CMs3187Specdb::CMs27986Specdb::CMs29777Specdb::CMs30122Specdb::CMs30222Specdb::CMs30647Specdb::CMs30890Specdb::CMs31328Specdb::CMs31329Specdb::CMs31946Specdb::CMs131871Specdb::CMs139605Specdb::EiMs1017Specdb::NmrOneD1299Specdb::NmrOneD1700Specdb::NmrOneD2742Specdb::NmrOneD3436Specdb::NmrOneD4818Specdb::NmrOneD4819Specdb::NmrOneD95938Specdb::NmrOneD95939Specdb::NmrOneD95940Specdb::NmrOneD95941Specdb::NmrOneD95942Specdb::NmrOneD95943Specdb::NmrOneD95944Specdb::NmrOneD95945Specdb::NmrOneD95946Specdb::NmrOneD95947Specdb::NmrOneD95948Specdb::NmrOneD95949Specdb::NmrOneD95950Specdb::NmrOneD95951Specdb::NmrOneD95952Specdb::NmrOneD95953Specdb::NmrOneD95954Specdb::NmrOneD95955Specdb::NmrOneD95956Specdb::MsMs1559Specdb::MsMs1560Specdb::MsMs1561Specdb::MsMs5272Specdb::MsMs5273Specdb::MsMs5274Specdb::MsMs5275Specdb::MsMs5276Specdb::MsMs5277Specdb::MsMs5281Specdb::MsMs5282Specdb::MsMs5283Specdb::MsMs5284Specdb::MsMs20600Specdb::MsMs20601Specdb::MsMs20602Specdb::MsMs22151Specdb::MsMs22152Specdb::MsMs22153Specdb::MsMs446630Specdb::MsMs446631Specdb::MsMs446632Specdb::MsMs446633Specdb::MsMs446634Specdb::MsMs447320Specdb::NmrTwoD1068Specdb::NmrTwoD1641HMDB01406936911C0015317154NIACINAMIDENCANiacinamideKeseler, 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?1358462677Purine nucleoside phosphorylase deoD-typeP0ABP8DEOD_ECOLIdeoDhttp://ecmdb.ca/proteins/P0ABP8.xmlPyrazinamidase/nicotinamidaseP21369PNCA_ECOLIpncAhttp://ecmdb.ca/proteins/P21369.xmldeacetylase of acs and cheY, regulates chemotaxisP75960cobBhttp://ecmdb.ca/proteins/P75960.xmlWater + Niacinamide > Nicotinic acid + AmmoniumNiacinamide + Water <> Nicotinic acid + AmmoniaR01268Nicotinamide riboside + Phosphate <> Niacinamide + alpha-D-Ribose 1-phosphateR02294Water + NAD <> Hydrogen ion + Adenosine diphosphate ribose + NiacinamideNADNUCLEOSID-RXNNiacinamide + Water > Hydrogen ion + Nicotinic acid + AmmoniaR01268NICOTINAMID-RXNWater + Nicotinamide ribotide <> Hydrogen ion + D-Ribose-5-phosphate + NiacinamideNMNNUCLEOSID-RXNNAD + an acetylprotein > Niacinamide + O-acetyl-ADP-ribose + a proteinNiacinamide + Water > Nicotinic acid + AmmoniaR01268NICOTINAMID-RXN48 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 GlucoBioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h44.2uM0.037 oCBW25113Stationary Phase, glucose limited1768000Ishii, 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