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

• ChemBase ID: 133036
• Molecular Formular: C9H12N2O5S
• Molecular Mass: 260.26698
• Monoisotopic Mass: 260.04669249
• SMILES: c1cn(c(=O)[nH]c1=S)[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1ccc(=S)[nH]c1=O
• InChI: 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
• InChIKey: ZLOIGESWDJYCTF-XVFCMESISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-sulfanylidene-1,2,3,4-tetrahydropyrimidin-2-one
• IUPAC Traditional name: thiouridine
• Synonyms: 4-Thiouridine

Database IDs

• CAS Number: 13957-31-8
• EC Number: 237-735-3
• MDL Number: MFCD00006538
• PubChem SID: 162227313; 24900212
• PubChem CID: 3032615

CALCULATED PROPERTIES

• Acid pKa: 7.8987784
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -1.5270832
• LogD (pH = 7.4): -1.6434304
• Log P: -1.5253725
• Molar Refractivity: 60.5565 cm^3
• Polarizability: 24.094425 Å^3
• Polar Surface Area: 102.26 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98%

DETAILS

Sigma Aldrich - T4509

Application
4-Thiouridine is a photoreactive (crosslinking) uridine analogue that upon phosphorylation to 4-thioUTP may be incorporated into RNA structures. 4-Thiouridine may be used to study the specificity and kinetics of uridine-cytidine kinases.