2.0 2012-05-31 13:44:57 -0600 2015-06-03 15:53:43 -0600 ECMDB01087 M2MDB000249 5-Methylthioribose S-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)ribose 5-Methylthio-D-ribose 5-Methylthioribose <i>S</i>-methyl-5-thio-D-ribofuranose MTR S(5)-Methyl-5-thio-D-ribose S-Methyl-5-thio-D-ribofuranose S5-Methyl-5-thio-D-ribose C6H12O4S 180.222 180.045629562 (2R,3R,4S,5S)-5-[(methylsulfanyl)methyl]oxolane-2,3,4-triol 5-methylthio-D-ribose 23656-67-9 CSC[C@H]1O[C@@H](O)[C@H](O)[C@@H]1O InChI=1S/C6H12O4S/c1-11-2-3-4(7)5(8)6(9)10-3/h3-9H,2H2,1H3/t3-,4-,5-,6-/m1/s1 OLVVOVIFTBSBBH-KVTDHHQDSA-N Solid Cytosol Extra-organism Periplasm logp -1.39 ALOGPS logs -0.01 ALOGPS solubility 1.76e+02 g/l ALOGPS logp -0.82 ChemAxon pka_strongest_acidic 11.31 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac (2R,3R,4S,5S)-5-[(methylsulfanyl)methyl]oxolane-2,3,4-triol ChemAxon average_mass 180.222 ChemAxon mono_mass 180.045629562 ChemAxon smiles CSC[C@H]1O[C@@H](O)[C@H](O)[C@@H]1O ChemAxon formula C6H12O4S ChemAxon inchi InChI=1S/C6H12O4S/c1-11-2-3-4(7)5(8)6(9)10-3/h3-9H,2H2,1H3/t3-,4-,5-,6-/m1/s1 ChemAxon inchikey OLVVOVIFTBSBBH-KVTDHHQDSA-N ChemAxon polar_surface_area 69.92 ChemAxon refractivity 40.79 ChemAxon polarizability 17.67 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Cysteine and methionine metabolism ec00270 S-adenosyl-L-methionine biosynthesis S-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 environment PW000837 Metabolic Spermidine biosynthesis and metabolism Spermidine 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. PW002085 Metabolic <i>S</i>-methyl-5'-thioadenosine degradation IV PWY0-1391 Specdb::CMs 17120 Specdb::CMs 37921 Specdb::CMs 169297 Specdb::NmrOneD 8562 Specdb::NmrOneD 8563 Specdb::NmrOneD 8564 Specdb::NmrOneD 8565 Specdb::NmrOneD 8566 Specdb::NmrOneD 8567 Specdb::NmrOneD 8568 Specdb::NmrOneD 8569 Specdb::NmrOneD 8570 Specdb::NmrOneD 8571 Specdb::NmrOneD 8572 Specdb::NmrOneD 8573 Specdb::NmrOneD 8574 Specdb::NmrOneD 8575 Specdb::NmrOneD 8576 Specdb::NmrOneD 8577 Specdb::NmrOneD 8578 Specdb::NmrOneD 8579 Specdb::NmrOneD 8580 Specdb::NmrOneD 8581 Specdb::MsMs 28586 Specdb::MsMs 28587 Specdb::MsMs 28588 Specdb::MsMs 35144 Specdb::MsMs 35145 Specdb::MsMs 35146 Specdb::MsMs 3053183 Specdb::MsMs 3053184 Specdb::MsMs 3053185 Specdb::MsMs 3114494 Specdb::MsMs 3114495 Specdb::MsMs 3114496 HMDB01087 494 388938 C03089 16895 CPD-560 Keseler, 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. 21097882 Kanehisa, 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. 22080510 Gianotti 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. 2153115 Della 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. 3091600 Carteni-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. 6838867 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI mtnN http://ecmdb.ca/proteins/P0AF12.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml 5'-Methylthioadenosine + Water > 5-Methylthioribose + Adenine R01401 METHYLTHIOADENOSINE-NUCLEOSIDASE-RXN 5'-Methylthioadenosine + Water <> Adenine + 5-Methylthioribose R01401 5'-S-methyl-5'-thioadenosine + Water > 5-Methylthioribose + Adenine PW_R005167