2.02012-05-31 14:34:40 -06002015-06-03 17:19:36 -0600ECMDB20238M2MDB0010815-Methylaminomethyl-2-thiouridine5-methylaminomethyl-2-thiouridine is a member of the chemical class known as Pyrimidine Nucleosides and Analogues. These are compounds comprising a pyrimidine base attached to a sugar. 5-methylaminomethyl-2-thiouridine is invovled in Selenouridine biosynthesis (tRNA). The selenium-modified nucleoside is 5-methyl-aminomethyl-2-selenouridine (mnm5Se2U), which is the chemical analog of 5-methylaminomethyl-2-thiouridine, a previously identified minor base of E. coli. tRNA2Glu. (PMID 6227514)2-Thio-5-methylaminomethyluridine5-((Methylamino)methyl)-2-thio-UridineC11H17N3O5S303.335303.0888913591-[(2S,3S,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-5-[(methylamino)methyl]-1,2-dihydropyrimidine-2-thione1-[(2S,3S,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-5-[(methylamino)methyl]pyrimidine-2-thione32860-54-1[H][C@@]1(CO)O[C@]([H])(N2C=C(CNC)C(O)=NC2=S)[C@@]([H])(O)[C@@]1([H])OInChI=1S/C11H17N3O5S/c1-12-2-5-3-14(11(20)13-9(5)18)10-8(17)7(16)6(4-15)19-10/h3,6-8,10,12,15-17H,2,4H2,1H3,(H,13,18,20)/t6-,7-,8-,10-/m0/s1HXVKEKIORVUWDR-GHCJXIJMSA-NCytoplasmPeriplasmlogp-1.40logs-2.07solubility2.60e+00 g/llogp-3.3pka_strongest_acidic7.74pka_strongest_basic9.22iupac1-[(2S,3S,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-5-[(methylamino)methyl]-1,2-dihydropyrimidine-2-thioneaverage_mass303.335mono_mass303.088891359smiles[H][C@@]1(CO)O[C@]([H])(N2C=C(CNC)C(O)=NC2=S)[C@@]([H])(O)[C@@]1([H])OformulaC11H17N3O5SinchiInChI=1S/C11H17N3O5S/c1-12-2-5-3-14(11(20)13-9(5)18)10-8(17)7(16)6(4-15)19-10/h3,6-8,10,12,15-17H,2,4H2,1H3,(H,13,18,20)/t6-,7-,8-,10-/m0/s1inchikeyHXVKEKIORVUWDR-GHCJXIJMSA-Npolar_surface_area117.78refractivity73.44polarizability29.61rotatable_bond_count4acceptor_count7donor_count5physiological_charge1formal_charge0Specdb::CMs1085477Specdb::EiMs3392Specdb::NmrOneD331302Specdb::NmrOneD331303Specdb::NmrOneD331304Specdb::NmrOneD331305Specdb::NmrOneD331306Specdb::NmrOneD331307Specdb::NmrOneD331308Specdb::NmrOneD331309Specdb::NmrOneD331310Specdb::NmrOneD331311Specdb::NmrOneD331312Specdb::NmrOneD331313Specdb::NmrOneD331314Specdb::NmrOneD331315Specdb::NmrOneD331316Specdb::NmrOneD331317Specdb::NmrOneD331318Specdb::NmrOneD331319Specdb::NmrOneD331320Specdb::NmrOneD331321Specdb::MsMs29033Specdb::MsMs29034Specdb::MsMs29035Specdb::MsMs35591Specdb::MsMs35592Specdb::MsMs35593303648823004885-METHYLAMINOMETHYL-2-THIOURIDINEKeseler, 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-D590.21097882van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25.17765195Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948.18331064Stadtman, T. C. (1983). "New biologic functions--selenium-dependent nucleic acids and proteins." Fundam Appl Toxicol 3:420-423.6227514tRNA 2-selenouridine synthaseP33667SELU_ECOLIselUhttp://ecmdb.ca/proteins/P33667.xml5-Methylaminomethyl-2-thiouridine + Phosphoroselenoic acid > 5-Methylaminomethyl-2-selenouridine + Inorganic phosphate