2.02012-05-31 13:44:57 -06002015-06-03 15:53:43 -0600ECMDB01087M2MDB0002495-MethylthioriboseS-methyl-5-thio-D-ribose is a product of the enzyme 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase. This enzyme catalyzes the irreversible cleavage of the glycosidic bond in 5'-methylthioadenosine (MTA) to produce adenine and the corresponding thioribose, 5'-methylthioribose.5-Deoxy-5-(methylthio)ribose5-Methylthio-D-ribose5-Methylthioribose<i>S</i>-methyl-5-thio-D-ribofuranoseMTRS(5)-Methyl-5-thio-D-riboseS-Methyl-5-thio-D-ribofuranoseS5-Methyl-5-thio-D-riboseC6H12O4S180.222180.045629562(2R,3R,4S,5S)-5-[(methylsulfanyl)methyl]oxolane-2,3,4-triol5-methylthio-D-ribose23656-67-9CSC[C@H]1O[C@@H](O)[C@H](O)[C@@H]1OInChI=1S/C6H12O4S/c1-11-2-3-4(7)5(8)6(9)10-3/h3-9H,2H2,1H3/t3-,4-,5-,6-/m1/s1OLVVOVIFTBSBBH-KVTDHHQDSA-NSolidCytosolExtra-organismPeriplasmlogp-1.39logs-0.01solubility1.76e+02 g/llogp-0.82pka_strongest_acidic11.31pka_strongest_basic-3.7iupac(2R,3R,4S,5S)-5-[(methylsulfanyl)methyl]oxolane-2,3,4-triolaverage_mass180.222mono_mass180.045629562smilesCSC[C@H]1O[C@@H](O)[C@H](O)[C@@H]1OformulaC6H12O4SinchiInChI=1S/C6H12O4S/c1-11-2-3-4(7)5(8)6(9)10-3/h3-9H,2H2,1H3/t3-,4-,5-,6-/m1/s1inchikeyOLVVOVIFTBSBBH-KVTDHHQDSA-Npolar_surface_area69.92refractivity40.79polarizability17.67rotatable_bond_count2acceptor_count4donor_count3physiological_charge0formal_charge0Cysteine and methionine metabolismec00270S-adenosyl-L-methionine biosynthesisS-adenosyl-L-methionine biosynthesis(SAM) is synthesized in the cytosol of the cell from L-methionine and ATP. This reaction is catalyzed by methionine adenosyltransferase. L methione is taken up from the environment through a complex reaction coupled transport and then proceeds too synthesize the s adenosylmethionine through a adenosylmethionine synthase. The S-adenosylmethionine then interacts with a hydrogen ion through a adenosylmethionine decarboxylase resulting in a carbon dioxide and a S-adenosyl 3-methioninamine.This compound interacts with a putrescine through a spermidine synthase resulting in a spermidine, a hydrogen ion and a S-methyl-5'-thioadenosine. The latter compound is degraded by interacting with a water molecule through a 5' methylthioadenosine nucleosidase resulting in a adenine and a S-methylthioribose which is then release into the environmentPW000837MetabolicSpermidine biosynthesis and metabolismSpermidine metabolism starts with S-adenosyl-L-methionine reacting with a hydrogen ion through a adenosylmethionine decarboxylase resulting in the release of a carbon dioxide and a S-adenosyl 3-(methylthio)propylamine. The later compound in turn reacts with putrescine resulting in the release of a hydrogen ion, a spermidine and a S-methyl-5'-thioadenosine. S-methyl-5'-thioadenosine in turn reacts with a water molecule through a 5-methylthioadenosine nucleosidase resulting in the release of a adenine and a S-methyl-5-thio-D-ribose which in in turn is released into the environment. PW002085Metabolic<i>S</i>-methyl-5'-thioadenosine degradation IVPWY0-1391Specdb::CMs17120Specdb::CMs37921Specdb::CMs169297Specdb::NmrOneD8562Specdb::NmrOneD8563Specdb::NmrOneD8564Specdb::NmrOneD8565Specdb::NmrOneD8566Specdb::NmrOneD8567Specdb::NmrOneD8568Specdb::NmrOneD8569Specdb::NmrOneD8570Specdb::NmrOneD8571Specdb::NmrOneD8572Specdb::NmrOneD8573Specdb::NmrOneD8574Specdb::NmrOneD8575Specdb::NmrOneD8576Specdb::NmrOneD8577Specdb::NmrOneD8578Specdb::NmrOneD8579Specdb::NmrOneD8580Specdb::NmrOneD8581Specdb::MsMs28586Specdb::MsMs28587Specdb::MsMs28588Specdb::MsMs35144Specdb::MsMs35145Specdb::MsMs35146Specdb::MsMs3053183Specdb::MsMs3053184Specdb::MsMs3053185Specdb::MsMs3114494Specdb::MsMs3114495Specdb::MsMs3114496HMDB01087494388938C0308916895CPD-560Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590.21097882Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.22080510Gianotti AJ, Tower PA, Sheley JH, Conte PA, Spiro C, Ferro AJ, Fitchen JH, Riscoe MK: Selective killing of Klebsiella pneumoniae by 5-trifluoromethylthioribose. Chemotherapeutic exploitation of the enzyme 5-methylthioribose kinase. J Biol Chem. 1990 Jan 15;265(2):831-7.2153115Della Ragione F, Carteni-Farina M, Gragnaniello V, Schettino MI, Zappia V: Purification and characterization of 5'-deoxy-5'-methylthioadenosine phosphorylase from human placenta. J Biol Chem. 1986 Sep 15;261(26):12324-9.3091600Carteni-Farina M, della Ragione F, Cacciapuoti G, Porcelli M, Zappia V: Transport and metabolism of 5'-methylthioadenosine in human erythrocytes. Biochim Biophys Acta. 1983 Jan 19;727(2):221-9.68388675'-methylthioadenosine/S-adenosylhomocysteine nucleosidaseP0AF12MTNN_ECOLImtnNhttp://ecmdb.ca/proteins/P0AF12.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xml5'-Methylthioadenosine + Water > 5-Methylthioribose + AdenineR01401METHYLTHIOADENOSINE-NUCLEOSIDASE-RXN5'-Methylthioadenosine + Water <> Adenine + 5-MethylthioriboseR014015'-S-methyl-5'-thioadenosine + Water > 5-Methylthioribose + AdeninePW_R005167