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

• ChemBase ID: 178591
• Molecular Formular: C9H12N2O5S
• Molecular Mass: 260.26698
• Monoisotopic Mass: 260.04669249
• SMILES: [C@H]1(C([C@@H](O[C@@H]1CO)n1c(=S)[nH]c(=O)cc1)O)O
• Canonical SMILES: OC[C@H]1O[C@H](C([C@H]1O)O)n1ccc(=O)[nH]c1=S
• 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
• InChIKey: GJTBSTBJLVYKAU-JDNPWWSISA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 20235-78-3
• PubChem SID: 164234501
• PubChem CID: 57375564

CALCULATED PROPERTIES

• Acid pKa: 8.010366
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -1.5266962
• LogD (pH = 7.4): -1.6194216
• Log P: -1.5253725
• Molar Refractivity: 60.5565 cm^3
• Polarizability: 24.098125 Å^3
• Polar Surface Area: 102.26 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 192-197°C

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - T384000

Modified nucleotide, essential for normal cell growth in some bacterial species. This compound is also able to chelate several metal ions.

REFERENCES

• Ikeuchi, Y., et al.: Mol. Cell, 21, 97 (2006)
• Odani, A., et al.: J. Inorg. Biochem., 101, 727 (2006)
• Wohlgamuth-Benedum, J., et al.: J. Biol. Chem., 284, 23947 (2006)