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CAS No. : | 19545-26-7 | MDL No. : | MFCD00133927 |
Formula : | C23H24O8 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QDLHCMPXEPAAMD-QAIWCSMKSA-N |
M.W : | 428.43 | Pubchem ID : | 312145 |
Synonyms : |
SL-2052;KY 12420;NSC 627609;BRN 0067676
|
Chemical Name : | (1S,6bR,9aS,11R,11bR)-1-(Methoxymethyl)-9a,11b-dimethyl-3,6,9-trioxo-1,6,6b,7,8,9,9a,10,11,11b-decahydro-3H-furo[4,3,2-de]indeno[4,5-h]isochromen-11-yl acetate |
Num. heavy atoms : | 31 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.57 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 8.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 105.71 |
TPSA : | 109.11 Ų |
GI absorption : | High |
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) : | -8.08 cm/s |
Log Po/w (iLOGP) : | 2.7 |
Log Po/w (XLOGP3) : | 1.18 |
Log Po/w (WLOGP) : | 2.54 |
Log Po/w (MLOGP) : | 0.94 |
Log Po/w (SILICOS-IT) : | 3.64 |
Consensus Log Po/w : | 2.2 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.1 |
Solubility : | 0.344 mg/ml ; 0.000803 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.07 |
Solubility : | 0.367 mg/ml ; 0.000857 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -5.15 |
Solubility : | 0.00301 mg/ml ; 0.00000703 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 5.66 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P271 | UN#: | N/A |
Hazard Statements: | H302+H332 | 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 |
---|---|---|
In dimethyl sulfoxide at 20 - 58℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With triethylamine In dimethyl sulfoxide at 20℃; | 2 Wortmannin (42.8 mg, 0.1 mmol), 6-aminohexanonic acid, referred to as 6-NH-hexanoic acid (65.5 mg, 0.5 mmol) and triethylamine (20 μl) were mixed in anhydrous DMSO (1 mL). The mixture was stirred at room temperature till complete (TLC monitoring). The final solution was purified by reverse phase HPLC with acetonitrile and water as solvents. The injection mixture was made by mixing reaction mixture with acetonitrile (containing 50% water) by 1 : 1 ratio just before the injection. After lyophilization, a yellow powder is obtained. 42.5 mg, 76.0%. MS: C29H37NOi0, cal. 560.2495 (M+H1"), found 560.2499; IH NMR, (CDCl3): 0.828 (3H, s, Cl 8-CH3), 1.430-1.507 (2H, m, -CH2CH2CH2-), 1.532 (3H, s, C19-CH3), 1.677-1.751 (4H, m, - CH2CH2CH2-), 1.859-1.904 (IH, dd, Jl=14.8Hz, J2=2.8Hz, H-12), 2.050 (3H5 s, CH3CO), 2.238-2.373 (3H, m, H-15, H-16), 2.416 (2H, t, J=7.4Hz, CH2CH2COOH), 2.542-2.629 (IH, m, H-12), 2.835-2.880(1H, m, CH3OCH2), 2.944-2.989 (IH, m, H-14), 3.137-3.259 (2H, m, H-15, CH3OCH2), 3.275 (3H, s, CH3OCH2), 3.417 (2H, q, Jl=13.0Hz, J2=6.5Hz), 4.328-4.345 (IH, m, H-I), 4.840 (2H, broad, OH), 5.982-6.009 (IH, m, H-11), 8.553 (IH, d, J=I 3.9Hz, H- 20), 9.810-9.920 (IH, m, NH). 13C NMR: 16 .839, 21.143, 22.593, 24.287, 26.049, 26.431, 30.452, 33.619, 36.710, 38.594, 42.356, 42.410, 50.041,59.419, 67.294, 73.330, 81.373, 88.431, 129.058, 137.093, 137.566, 151.134, 159.627, 166.403, 170.272, 178.010, 178.689, 218.285. This compound is 2b, see Figure 4. |
In dimethyl sulfoxide at 20 - 58℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98.7% | In dimethyl sulfoxide; at 20℃; for 0.5h; | WmC20-N-methyl-glucamine was prepared by combining wortmannin(21.4 mg, 0.05 mmol) and N-methyl-glucamine (19.5 mg, 0.1 mmol) in anhydrous DMSO (0.5 mL) at room temperature with stirring for 0.5 hours. The product was purified by HPLC and lyophilized. Yield 30.7 mg, 98.7%. A BSA wortmannin conjugate can be prepared by combining WmC20- N-methyl-glucamine (2.4 mg, 3.79chilO~3 mmol) with BSA (25 mg, 3.79xlO"4 mmol) in phosphate buffered saline (0.4 mL) at 37" C with stirring overnight. The mixture can be purified by size exclusion chromatography. The ratio of Wm to BSA in the product can be calculated using a standard curve.; A mixture of wortmannin (21.4 mg, 0.05 mmol) andN-methyl glucamine (19.5 mg, 0.1 mmol) in anhydrous DMSO (0.5 mL) was stirred at room temperature for 0.5 hours. The mixture was purified by HPLC. A yellow powder, termed WmC20N(Me) glucamine, was obtained after lyophilization. Yield, 30.7mg, 98.7%. A solution of Erbitux (aka cetuximab, 30mg) and WmC20N(Me)glucamine (1.36 mg, 2.18xlO'3 mmol) were combined in PBS (5 mL) at 37 C for 20 hours. Unreacted WmC20N(Me)glucamine was removed with a Sephadex G-50 column in ImM phosphate buffer at pH 7. After lyophilization, a yellow powder was obtained. The ratio of Wm to cetuximab (6.0 Wm/mole) was obtained from the absorbances of certuximab at 280nm and conjugated Wm at 408 ran. The coupling efficiency was 55%. The WmC20-centuximab can be checked for immunoreactivity by using A549 cells and erbitux. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | In dichloromethane at 20℃; for 15h; |