{"ymdb_id":"YMDB00178","created_at":"2011-05-29T16:04:13.000Z","updated_at":"2016-09-08T18:35:08.000Z","name":"5'-Methylthioadenosine","cas":"2457-80-9","state":"Solid","melting_point":"","description":"5'-Methylthioadenosine (MTA) is a side product in the biosynthesis of several important compounds. An important case is polyamine synthesis, where L-methionine is consumed through the utilization of S-adenosyl-L-methionine (SAM) in a reaction that releases MTA in the superpathway of polyamine biosynthesis. Polyamines (e.g. spermidine, putrescine, spermine) are a ubiquitous group of compounds involved in many biological processes, including binding to nucleic acids, stabilizing membranes, and stimulating several enzymes. MTA is recycled back to L-methionine during the methionine salvage pathway, which is found in a wide variety of organisms, including bacteria, protozoa, plants and mammals. [Biocyc PWY-6754 and POLYAMINSYN3-PWY and PWY-4361]","experimental_water_solubility":"","experimental_logp_hydrophobicity":"","location":"cytoplasm","synthesis_reference":"Sufrin, Janice R.; Spiess, Arthur J.; Kramer, Debora L.; Libby, Paul R.; Porter, Carl W. Synthesis and antiproliferative effects of novel 5'-fluorinated analogs of 5'-deoxy-5'-(methylthio)adenosine. Journal of Medicinal Chemistry (1989), 32(5), 997-1001.","chebi_id":"17509","hmdb_id":"HMDB01173","kegg_id":"C00170","pubchem_id":"149","cs_id":"388321","foodb_id":null,"wikipedia_link":null,"biocyc_id":"5-METHYLTHIOADENOSINE","iupac":"(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[(methylsulfanyl)methyl]oxolane-3,4-diol","traditional_iupac":"methylthioadenosine","logp":"-0.6084927256666669","pka":"14.012986053228548","alogps_solubility":"6.50e+00 g/l","alogps_logp":"-0.14","alogps_logs":"-1.66","acceptor_count":"7","donor_count":"3","rotatable_bond_count":"3","polar_surface_area":"119.31","refractivity":"74.02919999999999","polarizability":"29.256574959298177","formal_charge":"0","physiological_charge":"0","pka_strongest_basic":"3.9212883219836336","pka_strongest_acidic":"12.47183133876813","bioavailability":"1","number_of_rings":"3","rule_of_five":"1","ghose_filter":"0","veber_rule":"0","mddr_like_rule":"0","synonyms":["1-(6-amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio-beta-D-Ribofuranose","1-(6-amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio-beta-delta-Ribofuranose","5-Methylthioadenosine","5'-(Methylthio)-5'-deoxyadenosine","5'-(Methylthio)adenosine","5'-Deoxy-5'-(methylthio)adenosine","5'-Methylthioadenosine","5'-S-methyl-5'-thio-Adenosine","5'-S-Methyl-5'-thioadenosine","Methylthioadenosine","MTA","S-methyl-5-thioadenosine","S-methyl-5'-thioadenosine","Thiomethyladenosine"],"pathways":[{"name":"Cysteine and methionine metabolism","kegg_map_id":"00270"},{"name":"beta-Alanine metabolism","kegg_map_id":"00410"},{"name":"Methionine metabolism and salvage","kegg_map_id":null}],"growth_conditions":[],"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":18625006,"citation":"Pirkov, I., Norbeck, J., Gustafsson, L., Albers, E. (2008). \"A complete inventory of all enzymes in the eukaryotic methionine salvage pathway.\" FEBS J 275:4111-4120."},{"pubmed_id":14506228,"citation":"Subhi, A. L., Diegelman, P., Porter, C. W., Tang, B., Lu, Z. J., Markham, G. D., Kruger, W. D. (2003). \"Methylthioadenosine phosphorylase regulates ornithine decarboxylase by production of downstream metabolites.\" J Biol Chem 278:49868-49873."}],"proteins":[{"created_at":"2011-05-27T02:18:28.000Z","updated_at":"2011-05-27T15:01:17.000Z","name":"Spermine synthase","uniprot_id":"Q12455","uniprot_name":"SPSY_YEAST","enzyme":true,"transporter":false,"gene_name":"SPE4","num_residues":300,"molecular_weight":"34090.5","theoretical_pi":"4.77","general_function":"Involved in catalytic activity","specific_function":"S-adenosylmethioninamine + spermidine = 5'- methylthioadenosine + spermine","reactions":[{"id":1971,"direction":"\u003e","locations":"cytoplasm","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":2669,"direction":"\u003e","locations":null,"altext":"S-adenosylmethioninamine + spermidine = 5'-methylthioadenosine + spermine.","export":false,"pw_reaction_id":null,"source":null},{"id":3762,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006286","source":"Smpdb"}],"signal_regions":"None","transmembrane_regions":"None","pdb_id":null,"cellular_location":null,"genbank_gene_id":"AF067970","genbank_protein_id":"3201943","gene_card_id":"SPE4","chromosome_location":"chromosome 12","locus":"YLR146C","synonyms":["SPMSY","Spermidine aminopropyltransferase"],"enzyme_classes":["2.5.1.22"],"go_classes":[{"category":"Component","description":" Not Available"},{"category":"Function","description":" catalytic activity"},{"category":"Process","description":" Not Available"}],"pfams":[{"name":"Spermine_synth","identifier":"PF01564"}],"pathways":[{"name":"Cysteine and methionine metabolism","kegg_map_id":"00270"},{"name":"Arginine and proline metabolism","kegg_map_id":"00330"},{"name":"beta-Alanine metabolism","kegg_map_id":"00410"},{"name":"Glutathione metabolism","kegg_map_id":"00480"}],"gene_sequence":"ATGGTTAATAATTCACAGCATCCTTACATCAAAGATGGATGGTTTAGAGAGATTAATGATAAAAGTTTTCCGGGCCAGGCCTTTACTATGACCGTGGACTCAATACTTTATGAAGCCCGCAGTGAATTTCAGGACATCTTAATCTTCCGTAACAAGGTATACGGTACTGTTTTGGTCCTCGATGGTATTGTCCAATGTACGGAATTTGATGAGTTTGCCTATCAAGAGATGATCACCCACATTGCCATGTTTGCGCATTCTAATCCCAAGCGTGTACTTATCATTGGCGGTGGGGACGGAGGTGTCTTAAGGGAAGTAGCCAAGCACAGCTGTGTAGAAGATATCACTATGGTAGAAATTGACTCATCAGTGATCGAATTATCCCGTAAGTTCTTGCCCACATTGAGTAATGGTGCTTTCGATGACGAAAGGTTGGACTTGAAACTTTGCGATGGCTTCAAGTTCTTACAAGATATAGGTGCTTCCGACGTCCATAAGAAATTTGACGTCATTATTACAGATAGTTCTGATCCTGAAGGTCCAGCTGAAGCGTTTTTTCAAGAGAGGTATTTCGAACTATTGAAAGATGCTTTAAATCCTAATGGCGTTGTTATTATGCAAAGCTCTGAAAATTTTTGGTTAAATTTAAAATACTTACATGATTTGAAAAATACAGCCAAAAAGGTATTTCCTAATACAGAATATTGCTATACCATGGTTCCAACCTATACATCTGGCCAATTAGGTTTAATTGTTTGCAGTAATAACGCCAATATACCGTTGAACATTCCGCAAAGAAAGATATCTGAGCAAGAACAAGGGAAGCTGAAGTACTATAATCCTCAAATACATTCTAGTGCGTTTGTTTTGCCTACTTGGGCAGACAAGGTCATTAATGAATGA","protein_sequence":"MVNNSQHPYIKDGWFREINDKSFPGQAFTMTVDSILYEARSEFQDILIFRNKVYGTVLVLDGIVQCTEFDEFAYQEMITHIAMFAHSNPKRVLIIGGGDGGVLREVAKHSCVEDITMVEIDSSVIELSRKFLPTLSNGAFDDERLDLKLCDGFKFLQDIGASDVHKKFDVIITDSSDPEGPAEAFFQERYFELLKDALNPNGVVIMQSSENFWLNLKYLHDLKNTAKKVFPNTEYCYTMVPTYTSGQLGLIVCSNNANIPLNIPQRKISEQEQGKLKYYNPQIHSSAFVLPTWADKVINE"},{"created_at":"2011-05-27T02:18:58.000Z","updated_at":"2011-05-27T15:01:17.000Z","name":"Spermidine synthase","uniprot_id":"Q12074","uniprot_name":"SPEE_YEAST","enzyme":true,"transporter":false,"gene_name":"SPE3","num_residues":293,"molecular_weight":"33323.80078","theoretical_pi":"5.24","general_function":"Involved in catalytic activity","specific_function":"S-adenosylmethioninamine + putrescine = 5'-S- methyl-5'-thioadenosine + spermidine","reactions":[{"id":1970,"direction":"\u003e","locations":"cytoplasm","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":2670,"direction":"\u003e","locations":null,"altext":"S-adenosylmethioninamine + putrescine = 5'-S-methyl-5'-thioadenosine + spermidine.","export":false,"pw_reaction_id":null,"source":null},{"id":3759,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006283","source":"Smpdb"}],"signal_regions":"None","transmembrane_regions":"None","pdb_id":null,"cellular_location":null,"genbank_gene_id":"U27519","genbank_protein_id":"1326074","gene_card_id":"SPE3","chromosome_location":"chromosome 16","locus":"YPR069C","synonyms":["SPDSY","Putrescine aminopropyltransferase"],"enzyme_classes":["2.5.1.16"],"go_classes":[{"category":"Component","description":" Not Available"},{"category":"Function","description":" catalytic activity"},{"category":"Process","description":" Not Available"}],"pfams":[{"name":"Spermine_synth","identifier":"PF01564"}],"pathways":[{"name":"Cysteine and methionine metabolism","kegg_map_id":"00270"},{"name":"Arginine and proline metabolism","kegg_map_id":"00330"},{"name":"beta-Alanine metabolism","kegg_map_id":"00410"},{"name":"Glutathione metabolism","kegg_map_id":"00480"}],"gene_sequence":"ATGGCACAAGAAATCACTCACCCAACTATTGTAGACGGCTGGTTCAGAGAAATTTCTGATACCATGTGGCCAGGCCAGGCCATGACTTTAAAAGTGGAGAAAGTTTTACACCATGAGAAGTCAAAATATCAAGACGTTTTGATCTTCAAATCCACTACATATGGTAATGTTCTAGTTTTAGATAATGTAATTCAAGCCACCGAAAGGGATGAATTTGCCTACCAAGAAATGATTGCCCATCTTGCCTTGAATTCCCATCCAAATCCTAAGAAGGTTCTTGTTATTGGTGGGGGTGATGGTGGTGTTTTGAGAGAGGTTGTCAAGCATGATTCCGTTGAGGAAGCCTGGTTATGTGACATTGATGAAGCTGTTATTAGACTATCAAAGGAGTACCTACCAGAAATGGCTGCCTCTTATTCTCACCCAAAGGTTAAGACCCACATTGGTGATGGTTTCCAATTTTTAAGAGATTACCAAAACACATTTGACGTAATCATTACTGACTCTTCTGACCCAGAAGGTCCAGCTGAAACCCTTTTCCAAAAGGAATATTTCCAATTGTTGAACAGTGCGTTGACAGAAAAGGGTGTAATCACTACACAAGCAGAAAGTATGTGGATTCACTTGCCAATCATTAAGGACTTAAAGAAAGCCTGTTCTGAAGTTTTCCCAGTTGCAGAATACTCTTTCGTTACTATTCCAACTTACCCAACTGGTACGATTGGTTTTATGGTTTGCTCCAAAGATAAAACTTGCAATGTCAAGAAGCCACTACGTGAAATCTCTGATGAGAAGGAGGCTGAATTATACAGATACTATAACAAGAAAATTCACGAAGCTTCCTTTGTTCTACCAACCTGGGCAGCCAAGGAATTAAATTAG","protein_sequence":"MAQEITHPTIVDGWFREISDTMWPGQAMTLKVEKVLHHEKSKYQDVLIFKSTTYGNVLVLDNVIQATERDEFAYQEMIAHLALNSHPNPKKVLVIGGGDGGVLREVVKHDSVEEAWLCDIDEAVIRLSKEYLPEMAASYSHPKVKTHIGDGFQFLRDYQNTFDVIITDSSDPEGPAETLFQKEYFQLLNSALTEKGVITTQAESMWIHLPIIKDLKKACSEVFPVAEYSFVTIPTYPTGTIGFMVCSKDKTCNVKKPLREISDEKEAELYRYYNKKIHEASFVLPTWAAKELN"},{"created_at":"2011-05-27T03:18:34.000Z","updated_at":"2011-07-22T17:53:49.000Z","name":"Multicopy enhancer of UAS2","uniprot_id":"Q07938","uniprot_name":"MEU1_YEAST","enzyme":true,"transporter":false,"gene_name":"MEU1","num_residues":337,"molecular_weight":"37856.30078","theoretical_pi":"7.89","general_function":"Involved in catalytic activity","specific_function":"Seems to be implicated in the regulation of the expression of the ADH2 gene","reactions":[{"id":1200,"direction":"\u003e","locations":"cytoplasm","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":2714,"direction":"\u003e","locations":null,"altext":"S-methyl-5'-thioadenosine + phosphate = adenine + S-methyl-5-thio-alpha-D-ribose 1-phosphate","export":false,"pw_reaction_id":null,"source":null},{"id":3795,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006314","source":"Smpdb"}],"signal_regions":"None","transmembrane_regions":"None","pdb_id":null,"cellular_location":null,"genbank_gene_id":"X90564","genbank_protein_id":"975224","gene_card_id":"MEU1","chromosome_location":"chromosome 12","locus":"YLR017W","synonyms":[],"enzyme_classes":["2.4.2.28"],"go_classes":[{"category":"Component","description":" Not Available"},{"category":"Function","description":" transferase activity, transferring glycosyl groups"},{"category":"Function","description":" transferase activity, transferring pentosyl groups"},{"category":"Function","description":" catalytic activity"},{"category":"Function","description":" transferase activity"},{"category":"Process","description":" metabolic process"},{"category":"Process","description":" nitrogen compound metabolic process"},{"category":"Process","description":" cellular nitrogen compound metabolic process"},{"category":"Process","description":" nucleobase, nucleoside, nucleotide and nucleic acid metabolic process"},{"category":"Process","description":" nucleobase, nucleoside and nucleotide metabolic process"},{"category":"Process","description":" nucleoside metabolic process"}],"pfams":[{"name":"PNP_UDP_1","identifier":"PF01048"}],"pathways":[{"name":"Methionine metabolism and salvage","kegg_map_id":null}],"gene_sequence":"ATGAACAGGATTAAGAATACATTTTCTGTTGCTAAGAGATTAAAACTAAGCAAAGTTATGACGAACTCAGAATTACCGAGCATATTCGAAGGAACTGTTGATTTAGGGATTATTGGTGGTACAGGTTTATATAACCTTGACTGTCTGGAGCCCATCGCTTTGGTTCCACCCATGGTAACACCATGGGGTACCACATCGTCTCCTGTCACAATCTCTCAGTTCGTAGGAACTAACAGCCACTTTCACGTTGCGTTCATAGCCAGACACGGTATTAACCACGAATACCCACCCACTAAAGTCCCATTTAGAGCAAACATGGCGGCCTTAAAGAACTTAAATTGTAAAGCCGTTCTTTCTTTTAGTGCCGTGGGGTCTTTACAACCCCATATAAAGCCTAGAGATTTTGTGTTACCACAGCAAATAATCGACAGAACTAAAGGCATAAGACATTCTTCATATTTCAACGATGAAGGCTTGGTAGGTCACGTTGGTTTCGGACAGCCGTTCTCTCAAAAATTCGCAGAGTATATCTATCAATTCAAGAACGAGATAACAAATCCTGAATCCGAAGAACCGTGCCATTTGCATTACGACAAGGATATGACCGTTGTGTGTATGGAAGGCCCACAATTCTCCACGCGCGCTGAATCCAAGATGTACAGAATGTTTGGTGGCCATGTTATTAACATGAGTGTTATTCCAGAAGCCAAATTGGCGCGTGAGTGTGAGCTGCCTTACCAGATGATTTGTATGTCTACCGATTACGACGCATGGAGAGATGAGGCAGAACCTGTTACCGTAGAAACCGTTATTGGTAATTTGACGAATAATGGGCGCAATGCAAATATTTTAGCTTCTAAGATCATCGTCTCAATGGCCAAGGAAATCCCAGAGTTCATGCATACTGGCGATGGGCTGCGCGGTTCCATCAAGAAATCTATCTCTACCAAACCAGAGGCTATGTCCAAGGAAACCTTAGAAAGACTAAGATACTTATTTCCAAACTATTGGTAA","protein_sequence":"MNRIKNTFSVAKRLKLSKVMTNSELPSIFEGTVDLGIIGGTGLYNLDCLEPIALLPPMVTPWGTTSSPVTISQFVGTNSHFHVAFIARHGINHEYPPTKVPFRANMAALKNLNCKAVLSFSAVGSLQPHIKPRDFVLPQQIIDRTKGIRHSSYFNDEGLVGHVGFGQPFSQKFAEYIYQFKNEITNPESEEPCHLHYDKDMTVVCMEGPQFSTRAESKMYRMFGGHVINMSVIPEAKLARECELPYQMICMSTDYDAWRDEAEPVTVETVIGNLTNNGRNANILASKIIVSMAKEIPEFMHTGDGLRGSIKKSISTKPEAMSKETLERLRYLFPNYW"}]}