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Record Information
Version	2.0
Creation Date	2012-05-31 14:34:13 -0600
Update Date	2015-06-03 17:19:35 -0600
Secondary Accession Numbers	ECMDB20228
Identification
Name:	2-Thiouridine
Description	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]
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa71cede4> Close
Synonyms:	2-Thio-Uridine S2U S2U
Chemical Formula:	C9H12N2O5S
Weight:	Average: 260.267 Monoisotopic: 260.046692194
InChI Key:	GJTBSTBJLVYKAU-XVFCMESISA-N
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
CAS number:	20235-78-3
IUPAC Name:	1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1,2-dihydropyrimidine-2-thione
Traditional IUPAC Name:	1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxypyrimidine-2-thione
SMILES:	[H][C@]1(CO)O[C@@]([H])(N2C=CC(O)=NC2=S)[C@]([H])(O)[C@]1([H])O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as pyrimidine nucleosides. Pyrimidine nucleosides are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety.
Kingdom	Organic compounds
Super Class	Nucleosides, nucleotides, and analogues
Class	Pyrimidine nucleosides
Sub Class	Not Available
Direct Parent	Pyrimidine nucleosides
Alternative Parents	Glycosylamines Pentoses Pyrimidones Pyrimidinethiones 2-Thiopyrimidines Hydropyrimidines Vinylogous amides Tetrahydrofurans Heteroaromatic compounds Thioureas Secondary alcohols Lactams Oxacyclic compounds Azacyclic compounds Hydrocarbon derivatives Organic oxides Organonitrogen compounds Organopnictogen compounds Primary alcohols
Substituents	Pyrimidine nucleoside Glycosyl compound N-glycosyl compound Pentose monosaccharide Pyrimidinethione Pyrimidone 2-thiopyrimidine Thiopyrimidine Hydropyrimidine Pyrimidine Monosaccharide Vinylogous amide Heteroaromatic compound Tetrahydrofuran Secondary alcohol Thiourea Lactam Oxacycle Azacycle Organoheterocyclic compound Alcohol Organosulfur compound Organooxygen compound Organonitrogen compound Hydrocarbon derivative Organic oxide Organopnictogen compound Organic oxygen compound Primary alcohol Organic nitrogen compound Aromatic heteromonocyclic compound
Molecular Framework	Aromatic heteromonocyclic compounds
External Descriptors	thiouridine (CHEBI:60731 ) nucleoside analogue (CHEBI:60731 )
Physical Properties
State:	Not Available
Charge:	0
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 3.8 g/L ALOGPS logP -1 ALOGPS logP -1.2 ChemAxon logS -1.8 ALOGPS pKa (Strongest Acidic) 8.26 ChemAxon pKa (Strongest Basic) -3 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 105.75 Ų ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 60.88 m³·mol⁻¹ ChemAxon Polarizability 24.15 ų ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-004i-2940000000-32e460d66f652f5c9c27 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-004i-3910000000-cbd209a958722ab0756f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-00fr-9300000000-d060eac9afadd0aff7b0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0a4l-3590000000-4f4a4c0d815fed4bb0ed View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004l-7920000000-d64c330520eeb160cc3d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4i-9100000000-aa68d2267505e6d45c7f View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	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. Pubmed: 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. Pubmed: 18331064
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 60731 HMDB ID Not Available Pubchem Compound ID 3036443 Kegg ID Not Available ChemSpider ID 2300457 Wikipedia ID Not Available BioCyc ID 2-THIOURIDINE EcoCyc ID 2-THIOURIDINE Ligand Expo 2TU