1.0 2016-09-30 22:45:29 UTC 2020-06-04 20:55:32 UTC BMDB0001406 BMDB01406 Niacinamide Niacinamide, also known as nicotinamid or vitamin B3, belongs to the class of organic compounds known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group. Niacinamide exists as a solid, possibly soluble (in water), and a strong basic compound (based on its pKa) molecule. Niacinamide exists in all living species, ranging from bacteria to humans. Niacinamide participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylmethionine and niacinamide can be converted into S-adenosylhomocysteine and 1-methylnicotinamide through the action of the enzyme nicotinamide N-methyltransferase. In addition, Niacinamide and ribose-1-arsenate can be converted into nicotinamide riboside and phosphoric acid through its interaction with the enzyme purine nucleoside phosphorylase. In cattle, niacinamide is involved in the metabolic pathway called the nicotinate and nicotinamide metabolism pathway. Niacinamide is a potentially toxic compound. 3-Pyridinecarboxamide beta-Pyridinecarboxamide Niacin Nicotinamid Nicotinic acid amide Nicotinsaeureamid Nikotinamid Nikotinsaeureamid Vitamin b3 Vitamin PP Nicotinamide b-Pyridinecarboxamide Β-pyridinecarboxamide Nicotinate amide 3-Carbamoylpyridine 3-Pyridinecarboxylic acid amide Acid amide Amid kyseliny nikotinove Amide PP Aminicotin Amixicotyn Amnicotin Austrovit PP Benicot Delonin amide Dipegyl Dipigyl Endobion Factor PP Hansamid Inovitan PP m-(Aminocarbonyl)pyridine Mediatric NAM Nandervit-N Niacevit Niamide Niavit PP Nicamide Nicamina Nicamindon Nicasir Nicobion Nicofort Nicogen Nicomidol Nicosan 2 Nicosylamide Nicota Nicotamide Nicotilamide Nicotililamido Nicotinamida Nicotinamidum Nicotine acid amide Nicotine amide Nicotinic amide Nicotinsaureamid Nicotol Nicotylamide Nicotylamidum Nicovel Nicovit Nicovitina Nicovitol Nicozymin Nictoamide Niko-tamin Niocinamide Niozymin Papulex Pelmin Pelmine Pelonin amide PP-Faktor Propamine a Pyridine-3-carboxylic acid amide Savacotyl Vi-nicotyl Vi-noctyl Witamina PP 3 Pyridinecarboxamide Astra brand OF niacinamide b 3, Vitamin Niacinamide merck brand Pharmagenix brand OF niacinamide b3, Vitamin Enduramide Jenapharm, nicotinsäureamid Niacinamide jenapharm brand Niacinamide pharmagenix brand Jenapharm brand OF niacinamide Nicotinsäureamid jenapharm Vitamin b 3 Merck brand OF niacinamide Niacinamide astra brand Niacinamide 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 belongs to the class of organic compounds known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group. Organic compounds Organoheterocyclic compounds Pyridines and derivatives Pyridinecarboxylic acids and derivatives Nicotinamides Azacyclic compounds Heteroaromatic compounds Hydrocarbon derivatives Organic oxides Organonitrogen compounds Organooxygen compounds Organopnictogen compounds Primary carboxylic acid amides Aromatic heteromonocyclic compound Azacycle Carboxamide group Carboxylic acid derivative Heteroaromatic compound Hydrocarbon derivative Nicotinamide Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary carboxylic acid amide Aromatic heteromonocyclic compounds Pyridine alkaloids Water-soluble vitamins a vitamin an aliphatic amide pyridine alkaloid pyridinecarboxamide Solid melting_point 130 °C water_solubility 500 mg/mL at 25 °C logp -0.37 HANSCH,C ET AL. (1995) logp -0.45 ALOGPS logs -0.39 ALOGPS 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 number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Nicotinate and Nicotinamide Metabolism SMP0087241 Specdb::MsIr 1251 Specdb::MsIr 1252 Specdb::MsIr 1253 Specdb::EiMs 1017 Specdb::NmrTwoD 1068 Specdb::NmrTwoD 1641 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::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 Bladder Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Epidermis Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Fibroblasts Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Liver Metabolomics analysis was performed using GC-MS/LC-MS in multiparous Holstein dairy cows Shahzad K, Lopreiato V, Liang Y, Trevisi E, Osorio JS, Xu C, Loor JJ: Hepatic metabolomics and transcriptomics to study susceptibility to ketosis in response to prepartal nutritional management. J Anim Sci Biotechnol. 2019 Dec 18;10:96. doi: 10.1186/s40104-019-0404-z. eCollection 2019. 31867104 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Milk 5.6 +/- 2.5 uM Organic milk Superfoodly: https://www.superfoodly.com/nicotinamide-riboside-food-sources/ Milk 5.2 +/- 3.4 uM Conventional milk Superfoodly: https://www.superfoodly.com/nicotinamide-riboside-food-sources/ Milk 7.3 +/- 1.5 uM Raw milk (n=18) Trammell SA, Yu L, Redpath P, Migaud ME, Brenner C: Nicotinamide Riboside Is a Major NAD+ Precursor Vitamin in Cow Milk. J Nutr. 2016 May;146(5):957-63. doi: 10.3945/jn.116.230078. Epub 2016 Apr 6. 27052539 Milk Commercial, conventional whole milk Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8 Milk 10.6 +/- 0.2 uM Quantified by LC-MS/MS in 1% milk Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 10.4 +/- 0.2 uM Quantified by LC-MS/MS in 2% milk Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 11.3 +/- 0.2 uM Quantified by LC-MS/MS in 3.25% milk Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 10.3 +/- 0.3 uM Quantified by LC-MS/MS in skim milk Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 5.7 +/- 0.7 uM 1% milk by NMR Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 5.4 +/- 0.4 uM 2% milk by NMR Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 5 +/- 2 uM 3.25% milk by NMR Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 7 +/- 1 uM Skim milk by NMR Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk Samples collected from 1035 Friesian Holstein cows Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. 23438684 Muscle 135.28 +/- 8.64 uM Detected by NMR in Korean commercial beef sirloin. Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t. 20831251 Muscle 141.86 +/- 6.17 uM Detected by NMR in New Zealand commercial beef sirloin. Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t. 20831251 Muscle 90.35 +/- 6.44 uM Detected by NMR in Australian commercial beef sirloin. Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t. 20831251 Muscle 96.76 +/- 6.23 uM Detected by NMR in US commercial beef sirloin Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t. 20831251 Neuron Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Pancreas Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Placenta Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Prostate Tissue Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Spleen Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 C00153 FDB012485 DB02701 911 936 17154 C00000209 NIACINAMIDE 34058 Nicotinamide 1497 Galat, Alexander. Nicotinamide from nicotinonitrile by catalytic hydration. Journal of the American Chemical Society (1948), 70 3945. Agostini TS, Scherer R, Godoy HT: Simultaneous determination of B-group vitamins in enriched Brazilian dairy products. Crit Rev Food Sci Nutr. 2007;47(5):435-9. doi: 10.1080/10408390600846309. 17558655 Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. 23438684 Trammell SA, Yu L, Redpath P, Migaud ME, Brenner C: Nicotinamide Riboside Is a Major NAD+ Precursor Vitamin in Cow Milk. J Nutr. 2016 May;146(5):957-63. doi: 10.3945/jn.116.230078. Epub 2016 Apr 6. 27052539 Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation) Superfoodly: https://www.superfoodly.com/nicotinamide-riboside-food-sources/ BMDBP00100 Phenylethanolamine N-methyltransferase P10938 PNMT Enzyme BMDBP00136 tRNA 2'-phosphotransferase 1 Q3ZBM7 TRPT1 Enzyme BMDBP00698 Purine nucleoside phosphorylase P55859 PNP Enzyme BMDBP00830 Ecto-ADP-ribosyltransferase 5 Q0VC22 ART5 Enzyme BMDBP00831 NAD-dependent protein deacetylase sirtuin-7 Q0P595 SIRT7 Enzyme BMDBP00832 Poly [ADP-ribose] polymerase 1 P18493 PARP1 Enzyme BMDBP00833 NAD-dependent protein deacylase sirtuin-5, mitochondrial Q3ZBQ0 SIRT5 Enzyme BMDBP02942 Nicotinamide phosphoribosyltransferase F1MJ80 NAMPT Enzyme BMDBP02943 Bone marrow stromal cell antigen 1 F1MLP3 BST1 Enzyme