disodium (2R,5R)-2-[(hydrogen phosphonatooxy)methyl]-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-3-yl hydrogen phosphate

• ChemBase ID: 178598
• Molecular Formular: C10H14N2Na2O11P2
• Molecular Mass: 446.152022
• Monoisotopic Mass: 445.9868211
• SMILES: [nH]1c(=O)c(cn(c1=O)[C@H]1CC([C@H](O1)COP(=O)(O)[O-])OP(=O)(O)[O-])C.[Na+].[Na+]
• Canonical SMILES: O=c1[nH]c(=O)n(cc1C)[C@H]1CC([C@H](O1)COP(=O)(O)[O-])OP(=O)(O)[O-].[Na+].[Na+]
• InChI: InChI=1S/C10H16N2O11P2.2Na/c1-5-3-12(10(14)11-9(5)13)8-2-6(23-25(18,19)20)7(22-8)4-21-24(15,16)17;;/h3,6-8H,2,4H2,1H3,(H,11,13,14)(H2,15,16,17)(H2,18,19,20);;/q;2*+1/p-2/t6?,7-,8-;;/m1../s1
• InChIKey: RSEWRJOJVLPPMM-YEFJJUMZSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium (2R,5R)-2-[(hydrogen phosphonatooxy)methyl]-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-3-yl hydrogen phosphate
• IUPAC Traditional name: disodium (2R,5R)-2-[(hydrogen phosphonatooxy)methyl]-5-(5-methyl-2,4-dioxo-3H-pyrimidin-1-yl)oxolan-3-yl hydrogen phosphate
• Synonyms: 3'-Thymidylic Acid 5'-(Dihydrogen Phosphate) Disodium Salt; 2'-Deoxythymidine 3',5'-Diphosphate Disodium; 3',5'-Bisphospho-2'-deoxythymidine Disodium; 3',5'-TDP Disodium; Deoxythymidine 3',5'-Diphosphate Disodium; PTP Disodium; Thymidine 3',5'-Bisphosphate Disodium; Thymidine 3',5'-Diphosphate Disodium Salt

Database IDs

• CAS Number: 386229-77-2
• PubChem SID: 164234508
• PubChem CID: 71752550

CALCULATED PROPERTIES

• Acid pKa: 0.853058
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): -6.27177
• LogD (pH = 7.4): -8.533905
• Log P: -1.3661857
• Molar Refractivity: 74.9144 cm^3
• Polarizability: 30.953115 Å^3
• Polar Surface Area: 197.82 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White to Pale Gray Solid
• Melting Point: 178-180°C

Safety Information

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

DETAILS

Toronto Research Chemicals - T410000

A metabolite of Thymidine (T412000). Thymidine-3',5'-diphosphate (pTp) was used as a model compound for studies of reactions leading to strand breaks in DNA.

REFERENCES

• Iwahashi, K., et al.: J. Biochem., 90, 1685 (1981)
• Folkman, W., et al.: Chem. Res. Toxicol., 3, 536 (1981)