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

• ChemBase ID: 178592
• Molecular Formular: C9H12N2O5S
• Molecular Mass: 260.26698
• Monoisotopic Mass: 260.04669249
• SMILES: [C@H]1(C([C@@H](O[C@@H]1CO)n1c(=O)[nH]c(=S)cc1)O)O
• Canonical SMILES: OC[C@H]1O[C@H](C([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-JDNPWWSISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-sulfanylidene-1,2,3,4-tetrahydropyrimidin-2-one
• IUPAC Traditional name: 1-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-sulfanylidene-3H-pyrimidin-2-one
• Synonyms: Thiouridine; NSC 518132; 4-Thiouridine

Database IDs

• CAS Number: 13957-31-8
• PubChem SID: 164234502
• PubChem CID: 71199448

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

DETAILS

Toronto Research Chemicals - T384010

Nucleotide analogue, essential for cell growth in certain bacterial species. This compound is also able to chelate with certain metal ions, and in tRNA it can act as a built-in antiphotomutagenic agent that protects Escherichia coli cells against mutagene

REFERENCES

• Caldeira de Araujo, A., et al.: Embo J., 5, 175 (1986)
• Mishima, Y., et al.: Embo J., 14, 2679 (1986)