disodium [(2R,3S,5R)-3-fluoro-5-[5-(2H3)methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl]oxolan-2-yl]methyl phosphate

• ChemBase ID: 165944
• Molecular Formular: C10H12FN2Na2O7P
• Molecular Mass: 368.1631842
• Monoisotopic Mass: 368.01615415
• SMILES: [C@@H]1(C[C@@H](O[C@@H]1COP(=O)([O-])[O-])n1c(=O)[nH]c(=O)c(c1)C)F.[Na+].[Na+]
• Canonical SMILES: F[C@H]1C[C@@H](O[C@@H]1COP(=O)([O-])[O-])n1cc(C)c(=O)[nH]c1=O.[Na+].[Na+]
• InChI: InChI=1S/C10H14FN2O7P.2Na/c1-5-3-13(10(15)12-9(5)14)8-2-6(11)7(20-8)4-19-21(16,17)18;;/h3,6-8H,2,4H2,1H3,(H,12,14,15)(H2,16,17,18);;/q;2*+1/p-2/t6-,7+,8+;;/m0../s1
• InChIKey: KVBSTKVGADGIGP-ZJWYQBPBSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium [(2R,3S,5R)-3-fluoro-5-[5-(^2H₃)methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl]oxolan-2-yl]methyl phosphate
• IUPAC Traditional name: disodium [(2R,3S,5R)-3-fluoro-5-[5-(^2H₃)methyl-2,4-dioxo-3H-pyrimidin-1-yl]oxolan-2-yl]methyl phosphate
• Synonyms: 3'-Deoxy-3'-fluoro-5'-thymidylic Acid-d3 Disodium; 2',3'-Dideoxy-3'-fluoro-5-methyluridine-d3 5'-(Dihydrogen Phosphate) Disodium; 3'-Deoxy-3'-fluoro-thymidine-d3 Monophosphate Disodium; 3'-Fluoro-3'-deoxythymidine-d3 Monophosphate Disodium; 3'-Deoxy-3'-fluorothymidine-5'-monophosphate-d3 Disodium Salt

Database IDs

• PubChem SID: 162260077
• PubChem CID: 71315469

CALCULATED PROPERTIES

• Acid pKa: 1.2178723
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): -2.7943237
• LogD (pH = 7.4): -3.8901477
• Log P: -0.35152784
• Molar Refractivity: 62.3494 cm^3
• Polarizability: 25.512207 Å^3
• Polar Surface Area: 131.06 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 169-171°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D235482

A thymidine-5'-O-monophosphate analogue as inhibitors of Mycobacterium tuberculosis thymidylate kinase.

REFERENCES

• Jong, A., et al.: J. Biol. Chem., 259, 11052 ( 1984), Choi, Y., et al.: J. Med. Chem., 43, 2538 (2000)
• Stokstad, E., et al.: Science, 287, 2391 (2000)
• Li de La Sierra, I., et al.: J. Mol. Biol., 311, 87 (2000)