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CAS No. : | 987-78-0 | MDL No. : | MFCD00868097 |
Formula : | C14H26N4O11P2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 488.32 | Pubchem ID : | - |
Synonyms : |
Citicoline;Cytidine diphosphate-choline;Cytidine 5-diphosphocholine;CDP-Choline
|
Num. heavy atoms : | 31 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.71 |
Num. rotatable bonds : | 10 |
Num. H-bond acceptors : | 12.0 |
Num. H-bond donors : | 4.0 |
Molar Refractivity : | 102.47 |
TPSA : | 235.34 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -12.07 cm/s |
Log Po/w (iLOGP) : | -4.07 |
Log Po/w (XLOGP3) : | -3.93 |
Log Po/w (WLOGP) : | -1.48 |
Log Po/w (MLOGP) : | -7.59 |
Log Po/w (SILICOS-IT) : | -4.06 |
Consensus Log Po/w : | -4.23 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 1.0 |
Muegge : | 3.0 |
Bioavailability Score : | 0.11 |
Log S (ESOL) : | 0.13 |
Solubility : | 651.0 mg/ml ; 1.33 mol/l |
Class : | Highly soluble |
Log S (Ali) : | -0.42 |
Solubility : | 188.0 mg/ml ; 0.384 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | 0.47 |
Solubility : | 1450.0 mg/ml ; 2.98 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 5.23 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
115 mg | Inert atmosphere | A stirred suspensionof the free acid of CMP (100 mg, 0.31 mmol) in DMF (2 mL) and tributylamine(150 lL, 0.62 mmol) was heated for 10 min at 50 °C and allowed to cool at room temperature. Then, CDI (250 mg, 1.55 mmol) was added and the suspension turned to a clear solution after a few minutes. The anhydrous reaction mixture was stirred for 30 min at room temperature and treated with anhydrous methanol (100 lL, 2.48 mmol) to hydrolyze the CDI excess. After 30 min, anhydrous zinc chloride (59 mg, 0.43 mmol) was added followed by a solution of choline phosphate (0.77 M solution in anhydrous DMF, 2 mL,1.55 mmol). The reaction mixture was stirred for 24 h at room temperature. After evaporation of the solvents in vacuo, CDP-Cho 5 was puried by anion-exchange chromatography. The residue dissolved in waterwas puried bySephadex DEAE A-25 resin ion exchange column chromatography with a linear gradient 0–0.5 M of ammonium bicarbonate, followed by chromatography on RP-18. The triethylammonium counter ions were exchanged to sodium by passing the nucleotide solution through a Dowex 50WX8 column. 1-(b-D-ribofuranosyl)cytosine-5'-diphosphate choline (sodium salt) was obtained as a white solid after freeze-drying (115 mg, 74percent yield). HPLC: tR = 8.8 min (kmax276 nm); 1H NMR (400 MHz, D2O) d 7.86 (d, 1H, H6, J6-5 = 7.6 Hz), 6.04 (d, 1H,H5, J5-6 = 7.6 Hz), 5.92 (d, 1H, H10 , J10 -20 = 4.0 Hz), 4.31 (sl, 2H, CH2-O), 4.28–4.08(m, 5H, H20 H30 H40 H50 a H50 b), 3.60 (t, 2H, CH2-N, J = 4.2 Hz), 3.14 (s, 9H, CH3); 13CNMR (101 MHz, D2O) d 166.2 (s, C4), 157.7 (s, C2), 141.4 (s, C6), 96.6 (s, C5),89.3 (s, C10), 82.6 (d, C40, JC-P = 8.9 Hz), 74.1 (s, C20), 69.3 (s, C30), 65.9 (s, CH2N),64.7 (d, C50, JC-P = 5.1 Hz), 59.9 (s, CH2O), 53.9 (s, CH3); 31P NMR (162 MHz, D2O) d 11.35 (d, 2Jab = 21.4 Hz), 12.14 (d, 2Jab = 21.4 Hz); HRMS (ESI) m/z:[M+H]+ Calcd for C14H26N4O11NaP2 511.0971. Found 511.0973. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sulfuric acid In methanol at 50℃; for 3 h; | 2 (0.392 g, 1.0 mmol) was added to MeOH (10 mL)followed by the addition of 3 (0.310 g, 1.2 mmol) and was stirred atroom temperature for 10 min. Then 98percent H2SO4 (0.005 mL, 10 molpercent)was added. The mixture was kept at 50 °C for 3 h. The solvent wasremoved in vacuo and the residue was purified by recrystallisationfrom EtOH to give 1 as a white solid (0.410 g); yield 85percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | at 20℃; for 10 h; | Glycol phosphoryl cytidylic acid(4.29 g, 10 mmol) was added to a three-necked flask containing ethanol (50 mL)Trimethylamine gas (1.77 g, 30 mmol) was added,Stirring room temperature reaction 10h,Hydrochloric acid to pH 7,Filtered, the solvent removed under reduced pressure,Ethanol recrystallization,And the yield was 89percent. |