4-Thiouridine (4sU) - Moligand™, ≥98% , CAS No.13957-31-8

CAS: 13957-31-8 Cat. No.: T122953 Formula: C₉H₁₂N₂O₅S Molecular Weight: 260.27 EC Number: 237-735-3 PubChem CID: 3032615

GRADE & PURITY Moligand™, ≥98%

Synonyms

1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-4-thioxo-3,4-dihydropyrimidin-2(1H)-one | 1-β-D-Ribofuranosyl-4-thioxo-3,4-dihydro-2(1H)-pyrimidinone | RNA synthesis inhibitor | 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

4-Thiouridine is a photoreactive uridine analog.

Application：
4-Thiouridine has been used in labeling and isolation of nascent RNAs.

Specifications

Synonyms

1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-4-thioxo-3,4-dihydropyrimidin-2(1H)-one | 1-β-D-Ribofuranosyl-4-thioxo-3,4-dihydro-2(1H)-pyrimidinone | RNA synthesis inhibitor | 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

4-Thiouridine plays a role in assessing nascent RNA synthesis. It also enhances site-specific crosslinking. 4-Thiouridine also acts as a photoaffinity probe due to its stability even while lacking specific photoactivation. It can also be incorporated into

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

Pubchem Sid

504762339

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/504762339

Canonical Smiles

C1=CN(C(=O)NC1=S)C2C(C(C(O2)CO)O)O

IUPAC Name

1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-sulfanylidenepyrimidin-2-one

InChIKey

ZLOIGESWDJYCTF-XVFCMESISA-N

INCHI

1S/C9H12N2O5S/c12-3-4-6(13)7(14)8(16-4)11-2-1-5(17)10-9(11)15/h1-2,4,6-8,12-14H,3H2,(H,10,15,17)/t4-,6-,7-,8-/m1/s1

Isomeric SMILES

C1=CN(C(=O)NC1=S)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O

WGK Germany

3

PubChem CID

3032615

Molecular Weight

260.27

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Nucleosides, nucleotides, and analogues
    • Class Pyrimidine nucleosides

• Kingdom: Organic compounds
• Superclass: Nucleosides, nucleotides, and analogues
• Class: Pyrimidine nucleosides
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyrimidine nucleosides
• Alternative Parents: Glycosylamines Pentoses Pyrimidinethiones Pyrimidones Hydropyrimidines Tetrahydrofurans Thiolactams Heteroaromatic compounds Ureas Secondary alcohols Oxacyclic compounds Azacyclic compounds Primary alcohols Organosulfur compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Pyrimidine nucleoside - Glycosyl compound - N-glycosyl compound - Pentose monosaccharide - Pyrimidinethione - Pyrimidone - Hydropyrimidine - Monosaccharide - Pyrimidine - Heteroaromatic compound - Thiolactam - Tetrahydrofuran - Urea - Secondary alcohol - Oxacycle - Azacycle - Organoheterocyclic compound - Primary alcohol - Hydrocarbon derivative - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Organic oxide - Organopnictogen compound - Organic oxygen compound - Alcohol - Organic nitrogen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as pyrimidine nucleosides. These are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety.
• External Descriptors: thiouridine - nucleoside analogue

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Soluble in water (20 mg/ml), and methanol (10 mg/ml).
• Sensitivity: Air sensitive; Heat sensitive
• Molecular Weight: 260.269 g/mol
• XLogP3: -1.400
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 260.047 Da
• Monoisotopic Mass: 260.047 Da
• Topological Polar Surface Area: 134.000 Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 374.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1