methane; {[hydroxy({[(2R,3R,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy}phosphonic acid

• ChemBase ID: 178604
• Molecular Formular: C11H20N2O11P2
• Molecular Mass: 418.230822
• Monoisotopic Mass: 418.05423273
• SMILES: C.[C@H]1(C[C@@H](O[C@@H]1COP(=O)(OP(=O)(O)O)O)n1c(=O)[nH]c(=O)c(c1)C)O
• Canonical SMILES: O[C@@H]1C[C@@H](O[C@@H]1COP(=O)(OP(=O)(O)O)O)n1cc(C)c(=O)[nH]c1=O.C
• InChI: InChI=1S/C10H16N2O11P2.CH4/c1-5-3-12(10(15)11-9(5)14)8-2-6(13)7(22-8)4-21-25(19,20)23-24(16,17)18;/h3,6-8,13H,2,4H2,1H3,(H,19,20)(H,11,14,15)(H2,16,17,18);1H4/t6-,7-,8-;/m1./s1
• InChIKey: CHBFWCVCWZVODZ-QTPPMTSNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methane; {[hydroxy({[(2R,3R,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy}phosphonic acid
• IUPAC Traditional name: methane; {hydroxy[(2R,3R,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3H-pyrimidin-1-yl)oxolan-2-yl]methoxyphosphoryl}oxyphosphonic acid
• Synonyms: Thymidine 5'-(Trihydrogen Diphosphate) Sodium Salt; Thymidine 5'-Diphosphate Sodium Salt

Database IDs

• CAS Number: 108322-12-9
• PubChem SID: 164234514
• PubChem CID: 71752551

CALCULATED PROPERTIES

• Acid pKa: 1.7717481
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -6.06748
• LogD (pH = 7.4): -6.6995983
• Log P: -1.6644181
• Molar Refractivity: 77.1578 cm^3
• Polarizability: 31.347305 Å^3
• Polar Surface Area: 192.16 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T412010

A nucleoside diphosphate derived from phosphorylation of Thymidine (T412000). It is produced from Thymidine monophosphate by Thymidylate kinase (TMPK), a nucleoside monophosphate kinase and can be futher phosphorylated to its active triphosphate antiviral

REFERENCES

• Baumann, E.A. et al.: Biochim. Biphys. Acta Nucleic Acid Protein Synth., 565, 107 (1979)
• Kohler, J.J. et al.: Lab. Invest., 90, 383 (1979)