2-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3-thiazole-4-carboxamide

• ChemBase ID: 178628
• Molecular Formular: C9H12N2O5S
• Molecular Mass: 260.26698
• Monoisotopic Mass: 260.04669249
• SMILES: c1([C@H]2C([C@H]([C@H](O2)CO)O)O)nc(cs1)C(=O)N
• Canonical SMILES: OC[C@H]1O[C@H](C([C@H]1O)O)c1scc(n1)C(=O)N
• InChI: InChI=1S/C9H12N2O5S/c10-8(15)3-2-17-9(11-3)7-6(14)5(13)4(1-12)16-7/h2,4-7,12-14H,1H2,(H2,10,15)/t4-,5+,6?,7-/m1/s1
• InChIKey: FVRDYQYEVDDKCR-RDCZQUQVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3-thiazole-4-carboxamide
• IUPAC Traditional name: 2-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3-thiazole-4-carboxamide
• Synonyms: Tiazofurine; 2-β-D-Ribofuranosylthiazole-4-carboxamide; Tiazofurin; 2-β-D-Ribofuranosyl-4-thiazolecarboxamide; CI 909; NSC 286-193; NSC 286193; Riboxamide; TCAR

Database IDs

• CAS Number: 60084-10-8
• PubChem SID: 164234538
• PubChem CID: 44375352

CALCULATED PROPERTIES

• Acid pKa: 12.551733
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.033101
• LogD (pH = 7.4): -2.0331037
• Log P: -2.033101
• Molar Refractivity: 56.5307 cm^3
• Polarizability: 22.310472 Å^3
• Polar Surface Area: 125.9 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T437200

Tiazofurin has antitumor activity and is a potential therapeutic agent in the treatment of cancer. Tiazofurin acts as an inhibitor of Inosine-5'-monophosphate (IMP) dehydrogenase.

REFERENCES

• Streeter, D.G. et al.: Biochem. Biophys. Res. Comm., 115, 544 (1983)
• Boritzki, T. et al.: Biochem. Pharmacol., 34, 1109 (1983)
• Malek, K. et al.: Leuk. Res., 28, 1125 (1983)