2.0 2012-05-31 14:34:13 -0600 2015-06-03 17:19:35 -0600 ECMDB20228 M2MDB001073 2-Thiouridine 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. 2-thiouridine is invovled in tRNA-s2U34 biosynthesis. Thionucleosides are uniquely present in tRNA. In many organisms, tRNA specific for Lys, Glu, and Gln contain hypermodified 2-thiouridine (s(2)U) derivatives at wobble position 34. The s(2) group of s(2)U34 stabilizes anticodon structure, confers ribosome binding ability to tRNA and improves reading frame maintenance. [PMID:12549933] 2-Thio-Uridine S2U S²U C9H12N2O5S 260.267 260.046692194 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1,2-dihydropyrimidine-2-thione 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxypyrimidine-2-thione 20235-78-3 [H][C@]1(CO)O[C@@]([H])(N2C=CC(O)=NC2=S)[C@]([H])(O)[C@]1([H])O InChI=1S/C9H12N2O5S/c12-3-4-6(14)7(15)8(16-4)11-2-1-5(13)10-9(11)17/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,17)/t4-,6-,7-,8-/m1/s1 GJTBSTBJLVYKAU-XVFCMESISA-N Cytoplasm Periplasm logp -1.01 ALOGPS logs -1.84 ALOGPS solubility 3.80e+00 g/l ALOGPS logp -1.2 ChemAxon pka_strongest_acidic 8.26 ChemAxon pka_strongest_basic -3 ChemAxon iupac 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1,2-dihydropyrimidine-2-thione ChemAxon average_mass 260.267 ChemAxon mono_mass 260.046692194 ChemAxon smiles [H][C@]1(CO)O[C@@]([H])(N2C=CC(O)=NC2=S)[C@]([H])(O)[C@]1([H])O ChemAxon formula C9H12N2O5S ChemAxon inchi InChI=1S/C9H12N2O5S/c12-3-4-6(14)7(15)8(16-4)11-2-1-5(13)10-9(11)17/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,17)/t4-,6-,7-,8-/m1/s1 ChemAxon inchikey GJTBSTBJLVYKAU-XVFCMESISA-N ChemAxon polar_surface_area 105.75 ChemAxon refractivity 60.88 ChemAxon polarizability 24.15 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 1084662 Specdb::NmrOneD 336318 Specdb::NmrOneD 336319 Specdb::NmrOneD 336320 Specdb::NmrOneD 336321 Specdb::NmrOneD 336322 Specdb::NmrOneD 336323 Specdb::NmrOneD 336324 Specdb::NmrOneD 336325 Specdb::NmrOneD 336326 Specdb::NmrOneD 336327 Specdb::NmrOneD 336328 Specdb::NmrOneD 336329 Specdb::NmrOneD 336330 Specdb::NmrOneD 336331 Specdb::NmrOneD 336332 Specdb::NmrOneD 336333 Specdb::NmrOneD 336334 Specdb::NmrOneD 336335 Specdb::NmrOneD 336336 Specdb::NmrOneD 336337 Specdb::MsMs 25619 Specdb::MsMs 25620 Specdb::MsMs 25621 Specdb::MsMs 32177 Specdb::MsMs 32178 Specdb::MsMs 32179 3036443 2300457 2-THIOURIDINE 2TU 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 Winder, 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. 18331064