{"ymdb_id":"YMDB00224","created_at":"2011-05-29T16:08:42.000Z","updated_at":"2016-10-18T17:11:21.000Z","name":"Nicotinic acid","cas":"59-67-6","state":"Solid","melting_point":"236.6 oC","description":"Nicotinic acid (niacin or vitamin B3) is a water-soluble vitamin. It is a precursor to NAD+/NADH and NADP+/NADPH, which play essential metabolic roles in living cells. It is involved in both DNA repair, and the production of steroid hormones in the adrenal gland.","experimental_water_solubility":"18 mg/mL at 20 oC [YALKOWSKY,SH \u0026 HE,Y (2003)]","experimental_logp_hydrophobicity":"0.36 [SANGSTER (1993)]","location":"Cytoplasm, Extracellular, Mitochondrion","synthesis_reference":"McElvain, S. M.; Goese, M. A. Preparation of nicotinic acid from pyridine. Journal of the American Chemical Society (1941), 63 2283-4.","chebi_id":"15940","hmdb_id":"HMDB01488","kegg_id":"C00253","pubchem_id":"938","cs_id":"913","foodb_id":null,"wikipedia_link":"Niacin","biocyc_id":"NIACINE","iupac":"pyridine-3-carboxylic acid","traditional_iupac":"niacin","logp":"-0.16644564754087304","pka":null,"alogps_solubility":"8.31e+01 g/l","alogps_logp":"0.29","alogps_logs":"-0.17","acceptor_count":"3","donor_count":"1","rotatable_bond_count":"1","polar_surface_area":"50.19","refractivity":"31.157299999999996","polarizability":"11.303434426527051","formal_charge":"0","physiological_charge":"-1","pka_strongest_basic":"4.193250855836253","pka_strongest_acidic":"2.785610419861248","bioavailability":"1","number_of_rings":"1","rule_of_five":"1","ghose_filter":"0","veber_rule":"0","mddr_like_rule":"0","synonyms":["3-Carboxylpyridine","3-Carboxypyridine","3-Pyridinecarboxylate","3-Pyridinecarboxylic acid","3-Pyridylcarboxylate","3-Pyridylcarboxylic acid","Akotin","anti-Pellagra vitamin","Apelagrin","b-Pyridinecarboxylic acid","Daskil","Davitamon PP","Diacin","Direktan","Efacin","Enduracin","Kyselina nikotinova","Linic","M-Pyridinecarboxylic Acid","NAH","Naotin","Niac","niacin","niacine","Niacor","Nicacid","nicamin","Nicangin","NICO","Nico-Span","nicobid","nicocap","Nicocidin","Nicocrisina","Nicodan","Nicodelmine","Nicodon","nicolar","Niconacid","Niconat","Niconazid","Nicorol","Nicosan 3","Nicoside","Nicosyl","Nicotamin","Nicotene","Nicotil","Nicotinate","Nicotine Acid","Nicotinic acid","Nicotinipca","Nicotinsaure","Nicovasan","Nicovasen","Nicovel","Nicyl","Nipellen","Nyclin","Pellagramin","Pellagrin","Pelonin","Peviton","Pyridine-3-carbonic acid","Pyridine-3-carboxylic acid","Pyridine-beta-carboxylic acid","Pyridine-carboxylique-3","Pyridinecarboxylic Acid","Pyridylcarboxylic Acid","SK-Niacin","Slo-niacin","Tega-Span","Tinic","Vitamin B","Vitamin B3","Vitaplex N","wampocap"],"pathways":[{"name":"Nicotinate and nicotinamide metabolism","kegg_map_id":"00760"},{"name":"NAD metabolism","kegg_map_id":null}],"growth_conditions":[{"growth_media":"hops, malted barley","concentration":"2843.0","concentration_units":"\u0026#181;M","error":"0.0"},{"growth_media":"hops, malted barley","concentration":"42.0","concentration_units":"\u0026#181;M","error":"2.0"},{"growth_media":"grape juice","concentration":"18.0","concentration_units":"\u0026#181;M","error":"0.0"}],"references":[{"pubmed_id":21051339,"citation":"UniProt Consortium (2011). \"Ongoing and future developments at the Universal Protein Resource.\" Nucleic Acids Res 39:D214-D219."},{"pubmed_id":21062828,"citation":"Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). \"BRENDA, the enzyme information system in 2011.\" Nucleic Acids Res 39:D670-D676."},{"pubmed_id":18846089,"citation":"Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). \"A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology.\" Nat Biotechnol 26:1155-1160."},{"pubmed_id":19001417,"citation":"Belenky, P., Christensen, K. C., Gazzaniga, F., Pletnev, A. A., Brenner, C. (2009). \"Nicotinamide riboside and nicotinic acid riboside salvage in fungi and mammals. Quantitative basis for Urh1 and purine nucleoside phosphorylase function in NAD+ metabolism.\" J Biol Chem 284:158-164."},{"pubmed_id":21729004,"citation":"de Figueiredo, L. F., Gossmann, T. I., Ziegler, M., Schuster, S. (2011). \"Pathway Analysis of NAD+ metabolism.\" Biochem J :."},{"pubmed_id":null,"citation":"Alcoholic beverage, beer, regular, all - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. \u003ca href = http://www.ars.usda.gov/ba/bhnrc/ndl\u003eNutrient Data Laboratory Home Page\u003c/a\u003e"},{"pubmed_id":null,"citation":"Alcoholic beverage, wine, table, red - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. \u003ca href = http://www.ars.usda.gov/ba/bhnrc/ndl\u003eNutrient Data Laboratory Home Page\u003c/a\u003e"}],"proteins":[{"created_at":"2011-05-26T18:09:25.000Z","updated_at":"2011-05-27T15:01:03.000Z","name":"Nicotinamidase","uniprot_id":"P53184","uniprot_name":"PNC1_YEAST","enzyme":true,"transporter":false,"gene_name":"PNC1","num_residues":216,"molecular_weight":"24993.19922","theoretical_pi":"6.23","general_function":"Involved in catalytic activity","specific_function":"Catalyzes the deamidation of nicotinamide, an early step in the NAD(+) salvage pathway. Positively regulates SIR2-mediated silencing and longevity by preventing the accumulation of intracellular nicotinamide, an inhibitor of SIR2, during times of stress. Acts also on nicotinyl hydroxamate","reactions":[{"id":1775,"direction":"\u003c\u003e","locations":"mitochondrion;cytoplasm","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":2511,"direction":"\u003e","locations":"Cytoplasm. Nucleus. Peroxisome.","altext":"Nicotinamide + H(2)O = nicotinate + NH(3).","export":false,"pw_reaction_id":null,"source":null},{"id":4194,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006493","source":"Smpdb"}],"signal_regions":"None","transmembrane_regions":"None","pdb_id":null,"cellular_location":"Cytoplasm. Nucleus. Peroxisome.","genbank_gene_id":"AY558481","genbank_protein_id":"45270852","gene_card_id":"PNC1","chromosome_location":"chromosome 7","locus":"YGL037C","synonyms":["Nicotine deamidase","NAMase"],"enzyme_classes":["3.5.1.19"],"go_classes":[{"category":"Component","description":" Not Available"},{"category":"Function","description":" catalytic activity"},{"category":"Process","description":" metabolic process"}],"pfams":[{"name":"Isochorismatase","identifier":"PF00857"}],"pathways":[{"name":"Nicotinate and nicotinamide metabolism","kegg_map_id":"00760"},{"name":"NAD metabolism","kegg_map_id":null}],"gene_sequence":"ATGAAGACTTTAATTGTTGTTGATATGCAAAATGATTTTATTTCACCTTTAGGTTCCTTGACTGTTCCAAAAGGTGAGGAATTAATCAATCCTATCTCGGATTTGATGCAAGATGCTGATAGAGACTGGCACAGGATTGTGGTCACCAGAGATTGGCACCCTTCCAGACATATTTCGTTCGCAAAGAACCATAAAGATAAAGAACCCTATTCAACATACACCTACCACTCTCCAAGGCCAGGCGATGATTCCACGCAAGAGGGTATTTTGTGGCCCGTACACTGTGTGAAAAACACCTGGGGTAGTCAATTGGTTGACCAAATAATGGACCAAGTGGTCACTAAGCATATTAAGATTGTCGACAAGGGTTTCTTGACTGACCGTGAATACTACTCCGCCTTCCACGACATCTGGAACTTCCATAAGACCGACATGAACAAGTACTTAGAAAAGCATCATACAGACGAGGTTTACATTGTCGGTGTAGCTTTGGAGTATTGTGTCAAAGCCACCGCCATTTCCGCTGCAGAACTAGGTTATAAGACCACTGTCCTGCTGGATTACACAAGACCCATCAGCGATGATCCCGAAGTCATCAATAAGGTTAAGGAAGAGTTGAAGGCCCACAACATCAATGTCGTGGATAAATAA","protein_sequence":"MKTLIVVDMQNDFISPLGSLTVPKGEELINPISDLMQDADRDWHRIVVTRDWHPSRHISFAKNHKDKEPYSTYTYHSPRPGDDSTQEGILWPVHCVKNTWGSQLVDQIMDQVVTKHIKIVDKGFLTDREYYSAFHDIWNFHKTDMNKYLEKHHTDEVYIVGVALEYCVKATAISAAELGYKTTVLLDYTRPISDDPEVINKVKEELKAHNINVVDK"},{"created_at":"2011-05-27T03:22:51.000Z","updated_at":"2011-05-27T15:01:20.000Z","name":"Nicotinate phosphoribosyltransferase","uniprot_id":"P39683","uniprot_name":"NPT1_YEAST","enzyme":true,"transporter":false,"gene_name":"NPT1","num_residues":429,"molecular_weight":"49018.19922","theoretical_pi":"6.92","general_function":"Involved in nicotinate phosphoribosyltransferase activity","specific_function":"Essential for growth under anaerobic conditions","reactions":[{"id":1768,"direction":"\u003e","locations":"mitochondrion;cytoplasm","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":2722,"direction":"\u003e","locations":"Cytoplasm. Nucleus","altext":"Nicotinate D-ribonucleotide + diphosphate = nicotinate + 5-phospho-alpha-D-ribose 1-diphosphate.","export":false,"pw_reaction_id":null,"source":null},{"id":4193,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006492","source":"Smpdb"}],"signal_regions":"None","transmembrane_regions":"None","pdb_id":"1VLP","cellular_location":"Cytoplasm. Nucleus","genbank_gene_id":"Z75117","genbank_protein_id":"1420489","gene_card_id":"NPT1","chromosome_location":"chromosome 15","locus":"YOR209C","synonyms":["NAPRTase"],"enzyme_classes":["2.4.2.11"],"go_classes":[{"category":"Component","description":" intracellular part"},{"category":"Component","description":" cytoplasm"},{"category":"Component","description":" cell part"},{"category":"Function","description":" transferase activity, transferring pentosyl groups"},{"category":"Function","description":" catalytic activity"},{"category":"Function","description":" transferase activity"},{"category":"Function","description":" transferase activity, transferring glycosyl groups"},{"category":"Function","description":" nicotinate phosphoribosyltransferase activity"},{"category":"Process","description":" nucleotide metabolic process"},{"category":"Process","description":" cellular metabolic process"},{"category":"Process","description":" cofactor metabolic process"},{"category":"Process","description":" coenzyme metabolic process"},{"category":"Process","description":" coenzyme biosynthetic process"},{"category":"Process","description":" pyridine nucleotide biosynthetic process"},{"category":"Process","description":" metabolic process"},{"category":"Process","description":" nicotinamide nucleotide biosynthetic process"},{"category":"Process","description":" NAD biosynthetic process"},{"category":"Process","description":" nitrogen compound metabolic process"},{"category":"Process","description":" nucleotide biosynthetic process"},{"category":"Process","description":" cellular nitrogen compound metabolic process"},{"category":"Process","description":" nucleobase, nucleoside, nucleotide and nucleic acid metabolic process"},{"category":"Process","description":" nicotinate nucleotide biosynthetic process"},{"category":"Process","description":" nucleobase, nucleoside and nucleotide metabolic process"},{"category":"Process","description":" nucleoside phosphate metabolic process"}],"pfams":[{"name":"NAPRTase","identifier":"PF04095"}],"pathways":[{"name":"Nicotinate and nicotinamide metabolism","kegg_map_id":"00760"},{"name":"NAD metabolism","kegg_map_id":null}],"gene_sequence":"ATGTCAGAACCAGTGATAAAGTCTCTTTTGGACACAGACATGTACAAGATTACGATGCATGCTGCTGTCTTCACTAATTTTCCAGATGTTACAGTTACTTATAAATATACCAACAGGTCGTCCCAATTGACCTTCAATAAGGAAGCCATTAATTGGTTGAAAGAGCAATTTTCGTATTTGGGAAATTTGAGGTTCACAGAAGAGGAAATTGAATACTTAAAACAGGAAATCCCATATTTGCCATCGGCATATATTAAGTATATTAGCAGTTCTAATTACAAACTACACCCTGAAGAGCAGATTTCCTTCACTTCAGAAGAAATCGAGGGCAAGCCCACCCACTACAAATTGAAAATTTTAGTCAGTGGTAGTTGGAAGGATACTATCCTTTATGAGATCCCCTTACTGTCCCTAATATCAGAAGCGTATTTTAAATTTGTTGACATCGACTGGGACTACGAAAACCAATTAGAACAAGCTGAGAAGAAGGCGGAAACTTTGTTTGATAATGGTATTAGATTCAGTGAATTTGGTACAAGACGTCGTAGATCTCTGAAGGCTCAAGATCTAATTATGCAAGGAATCATGAAAGCTGTGAACGGTAACCCAGACAGAAACAAATCGCTATTATTAGGCACATCAAATATTTTATTTGCCAAGAAATATGGAGTCAAGCCAATCGGTACTGTGGCTCACGAGTGGGTTATGGGAGTCGCTTCTATTAGTGAAGATTATTTGCATGCCAATAAAAATGCAATGGATTGTTGGATCAATACTTTTGGTGCAAAAAATGCTGGTTTAGCATTAACGGATACTTTTGGAACTGATGACTTTTTAAAATCATTCCGTCCACCATATTCTGATGCTTACGTCGGTGTTAGACAAGATTCTGGAGACCCAGTTGAGTATACCAAAAAGATTTCCCACCATTACCATGACGTGTTGAAATTGCCTAAATTCTCGAAGATTATCTGTTATTCCGATTCTTTGAACGTCGAAAAGGCAATAACTTACTCCCATGCAGCTAAAGAGAATGGAATGCTAGCCACATTCGGTATTGGCACAAACTTTACTAATGATTTTCGTAAGAAGTCAGAACCCCAGGTTAAAAGTGAGCCGTTAAACATCGTTATCAAACTATTAGAAGTAAATGGTAATCACGCTATCAAAATTTCTGATAACTTAGGTAAAAATATGGGAGATCCTGCCACTGTGAAGAGAGTGAAAGAGGAATTGGGATATACTGAACGAAGTTGGAGTGGTGATAACGAAGCGCACAGATGGACCTAA","protein_sequence":"MSEPVIKSLLDTDMYKITMHAAVFTNFPDVTVTYKYTNRSSQLTFNKEAINWLKEQFSYLGNLRFTEEEIEYLKQEIPYLPSAYIKYISSSNYKLHPEEQISFTSEEIEGKPTHYKLKILVSGSWKDTILYEIPLLSLISEAYFKFVDIDWDYENQLEQAEKKAETLFDNGIRFSEFGTRRRRSLKAQDLIMQGIMKAVNGNPDRNKSLLLGTSNILFAKKYGVKPIGTVAHEWVMGVASISEDYLHANKNAMDCWINTFGAKNAGLALTDTFGTDDFLKSFRPPYSDAYVGVRQDSGDPVEYTKKISHHYHDVLKLPKFSKIICYSDSLNVEKAITYSHAAKENGMLATFGIGTNFTNDFRKKSEPQVKSEPLNIVIKLLEVNGNHAIKISDNLGKNMGDPATVKRVKEELGYTERSWSGDNEAHRWT"},{"created_at":"2011-05-27T09:34:55.000Z","updated_at":"2011-05-27T15:01:30.000Z","name":"High-affinity nicotinic acid transporter","uniprot_id":"P53322","uniprot_name":"TNA1_YEAST","enzyme":false,"transporter":true,"gene_name":"TNA1","num_residues":534,"molecular_weight":"60134.30078","theoretical_pi":"6.83","general_function":"Involved in transmembrane transport","specific_function":"Involved in the uptake of nicotinic acid","reactions":[],"signal_regions":"None","transmembrane_regions":"131-151;153-173;188-208;218-238;251-271;324-344;356-376;385-405;411-431;445-465;475-495","pdb_id":null,"cellular_location":"Membrane; Multi-pass membrane protein","genbank_gene_id":"Y07777","genbank_protein_id":"1536952","gene_card_id":"TNA1","chromosome_location":"chromosome 7","locus":"YGR260W","synonyms":["Nicotinic acid permease"],"enzyme_classes":[],"go_classes":[{"category":"Component","description":" Not Available"},{"category":"Function","description":" Not Available"},{"category":"Process","description":" transmembrane transport"},{"category":"Process","description":" establishment of localization"},{"category":"Process","description":" transport"}],"pfams":[{"name":"MFS_1","identifier":"PF07690"}],"pathways":[],"gene_sequence":"ATGAGCAACAAATTTACAATGGAGTCACCTAAGCATTTGGTGGATGATGTGCTTTTCATATCACCCACCAATGATGGATCAGAAGAAAAGCCTACGGAAGTCACGTTCCAGGAAGATGAAGGCCATGACGCTAGCTTGCATAATCGCAGCCATGACAAGAAGTCGGAACTTGCCACCGAACGGGAAATTATGGCTACTACCACGGATGATGACGGCATCCCCTCCCCTTCCCATCCAATGGAAAAGCGTGTCTTGCGCAAAATGGATATATACTTGATTCCTCTTATGGGGATGCTATATTTCCTTTCTAACCTGGATAAATCGAATATTGGTAACGCAGAAGTTGCAGGTCTATCCAAGGATATCCACCTTGTAGGAACGCAATATAACACATGTGTCACAGTTTTTTTCGCGACGTATGTTCTTTTCGACCCCATAGGTACTAACCTTCTGAAAATTATGGGTCCGCCATTAATGATGAGTATCTGTTTGACCTGTTTCGGTGCTATTTCGCTCGGAACTGCTTGGGTTAAGAATTATGCTCAATTGATCGTTGTCAGACTACTACTGGGTGCCTTTGAAGGTATGATTTATCCCGCTATTAACATGTACCTTTCAGTCTGCTATAGAAGAGAACAATATGCTCTGAGGTTCGCTTTTGTCTTCAGTGCAGCCTGTTTGTCTTCATCTTTTGGTGGGCTGATTGCTTATGGTTGTTCCAAAATCAGCGGTTCTCTAAAGGACTGGCAATACATTTACATTGTCGAAGGTTGTATCTCTTTGGGGTTCGTACCATTCTATGCCTTCGGGTTGAGCAAAAATTTGGAGGATTCGTGGTTTTTCAATAAGGAGGAAAAAGAGTACATTTCCGAAAGATACAAGACTATGAACACTTTTGACCCGGACGAAAAATTTGAATGGTTCCAAGTGTGGCAAGCAGTTAAGGATGTCAAGACTTGGGCTAGTGCTGTGGCATTATTCGGTATCGATTTGACTACTTTTGGTCTAACAGTCTTCTTGCCGATCATCATTACCAGTATGGGGTTCACTAATGTCAGAGCTCAATTAATGACCGTGCCCATCTATTTCCTTACAGCAATTGTGTTCTTCATTTGTGCCGTTTGGTCTGATCGTATAAAGTTGAGATCTCCATTCATCCTGGGTGCTTGTCTGACGACTTCGATAGGCATAGCTATCGTCCTTGGTTCTCAAGTTCATGGTGTGAGATATTTTGGCGTTTACATTCTTTGTATGGGTATTTACGTTAATGCTGCCTGTAACTGTTTATGGTTAAGTGGTAACACTGGTAATTACTTCAAGAGAGCCACCGCTTTAGGAATTAATCTATTTTTCGGGTCTGGTTCAGGGTTGGTCTCTGGTCAAATTTTTGTTGCCAAAGACAAGCCAAGATATATCAAAGGGCTGTCGATTAGTCTGGCCTTTCAAGTCTTCTCCATATTTATGACGGTTGTGCAAATTTTCCTATACAAGAGGGAAAACGATAAAAAGAAAGCAATAATAGATCGCTGTAATGAATTGGGAGAGCCTATTCCATACGACGAAAGGTTAAGCGACAAAAACCCTGAGTTTAAGTACATGTATTAG","protein_sequence":"MSNKFTMESPKHLVDDVLFISPTNDGSEEKPTEVTFQEDEGHDASLHNRSHDKKSELATEREIMATTTDDDGIPSPSHPMEKRVLRKMDIYLIPLMGMLYFLSNLDKSNIGNAEVAGLSKDIHLVGTQYNTCVTVFFATYVLFDPIGTNLLKIMGPPLMMSICLTCFGAISLGTAWVKNYAQLIVVRLLLGAFEGMIYPAINMYLSVCYRREQYALRFAFVFSAACLSSSFGGLIAYGCSKISGSLKDWQYIYIVEGCISLGFVPFYAFGLSKNLEDSWFFNKEEKEYISERYKTMNTFDPDEKFEWFQVWQAVKDVKTWASAVALFGIDLTTFGLTVFLPIIITSMGFTNVRAQLMTVPIYFLTAIVFFICAVWSDRIKLRSPFILGACLTTSIGIAIVLGSQVHGVRYFGVYILCMGIYVNAACNCLWLSGNTGNYFKRATALGINLFFGSGSGLVSGQIFVAKDKPRYIKGLSISLAFQVFSIFMTVVQIFLYKRENDKKKAIIDRCNELGEPIPYDERLSDKNPEFKYMY"}]}