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

CAS: 13957-31-8 Cat. No.: T122953 Peso molecular: 260.27 Número EC: 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

Descripción general

4-Thiouridine is a photoreactive uridine analog.

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

Specifications

Sinónimos

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-

Especificaciones y pureza

Moligand™, ≥98%

Mecanismos bioquímicos y fisiológicos

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

Condiciones de almacenamiento de almacenamiento

Store at -20°C

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Grado

Moligand™

Nota

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.

Pureza

≥98%

Nombres e identificadores

• Pubchem Sid: 504762339
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504762339
• Sonrisas canónicas: 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
• Isómeros SMILES: C1=CN(C(=O)NC1=S)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
• WGK Alemania: 3
• PubChem CID: 3032615
• Peso molecular: 260.27

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Nucleosides, nucleotides, and analogues
• Clase: 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
• Descripción: 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

Propiedades químicas y físicas

• Solubilidad: Soluble in water (20 mg/ml), and methanol (10 mg/ml).
• Sensibilidad: Air sensitive; Heat sensitive
• Peso molecular: 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

Referencias

1. Xiuying Lin, Qianhui Zhang, Yichao Qin, Qisheng Zhong, Daizhu Lv, Xiaopeng Wu, Pengcheng Fu, Huan Lin.  (2022)  Potential Misidentification of Natural Isomers and Mass-Analogs of Modified Nucleosides by Liquid Chromatography–Triple Quadrupole Mass Spectrometry.  Genes,  13  (5): (878).  [PMID:35627263] [10.3390/genes13050878]

2. Yin Kun, Xu Yiling, Guo Ye, Zheng Zhong, Lin Xinrui, Zhao Meijuan, Dong He, Liang Dianyi, Zhu Zhi, Zheng Junhua, Lin Shichao, Song Jia, Yang Chaoyong.  (2024)  Dyna-vivo-seq unveils cellular RNA dynamics during acute kidney injury via in vivo metabolic RNA labeling-based scRNA-seq.  Nature Communications,  15  (1): (1-14).  [PMID:39543112] [10.1038/s41467-024-54202-4]

3. Huihui An, Yifan Hong, Yeek Teck Goh, Casslynn W.Q. Koh, Shahzina Kanwal, Yi Zhang, Zhaoqi Lu, Phoebe M.L. Yap, Suat Peng Neo, Chun-Ming Wong, Alice S.T. Wong, Yang Yu, Jessica Sook Yuin Ho, Jayantha Gunaratne, Wee Siong Sho Goh.  (2024)  m6Am sequesters PCF11 to suppress premature termination and drive neuroblastoma differentiation.  MOLECULAR CELL,      [PMID:39481383] [10.1016/j.molcel.2024.10.004]

4. Xinyi Wan, Haonan Fan, Zhuoning Li, Yixuan Du, Yu Liu, Weiwu Zeng, Zhongxing Sun, Juejia Shao, Junqi Jia, Yanjun Zhang, Dong Fang.  (2025)  MYC drives left-handed Z-DNA formation to shape gene expression.  Nature Communications,      [PMID:41326407] [10.1038/s41467-025-66886-3]