Structure of 4971-56-6
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 4971-56-6 |
Formula : | C4H4O3 |
M.W : | 100.07 |
SMILES Code : | O=C(C1)OCC1=O |
MDL No. : | MFCD00010086 |
Boiling Point : | No data available |
InChI Key : | JCGNDDUYTRNOFT-UHFFFAOYSA-N |
Pubchem ID : | 521261 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319 |
Precautionary Statements: | P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 |
Num. heavy atoms | 7 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.5 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 20.71 |
TPSA ? Topological Polar Surface Area: Calculated from |
43.37 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.63 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.14 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-0.5 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.89 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.07 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.03 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.37 |
Solubility | 42.5 mg/ml ; 0.424 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.32 |
Solubility | 48.3 mg/ml ; 0.482 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-0.43 |
Solubility | 37.4 mg/ml ; 0.373 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-7.01 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
2.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.19 |
* 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 |
---|---|---|
96% | In ethanol; for 1h;Reflux; | General procedure: The compound tetronic acid (102 mg, 1.02 mmol) was dissolved in 4 mL of ethanol, followed by addition of 3,4,5-trimethoxybenzaldehyde (200 mg, 1.02 mmol) and 2,4-dimethoxypyrimidine-5-amine (158 mg, 1.02 mmol). The reaction mixture was reflux at ethanol temperature for 1 h. Then reaction mixture was allowed to cool to room temperature, and the precipitated product was collected by vacuum filtration and washed with ethanol (3 mL) then recrystallized from ethanol to afford pure compound 11a as a white solid in 390 mg, 92percent yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | In ethanol; for 1h;Reflux; | General procedure: The compound tetronic acid (102 mg, 1.02 mmol) was dissolved in 4 mL of ethanol, followed by addition of 3,4,5-trimethoxybenzaldehyde (200 mg, 1.02 mmol) and 2,4-dimethoxypyrimidine-5-amine (158 mg, 1.02 mmol). The reaction mixture was reflux at ethanol temperature for 1 h. Then reaction mixture was allowed to cool to room temperature, and the precipitated product was collected by vacuum filtration and washed with ethanol (3 mL) then recrystallized from ethanol to afford pure compound 11a as a white solid in 390 mg, 92percent yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | In ethanol; for 1h;Reflux; | General procedure: The compound tetronic acid (100 mg, 1 mmol) was dissolved in 4 mL of ethanol, followed by the addition of 3,4,5-trimethoxybenzaldehyde (5a) (196 mg, 1 mmol) and 3-phenyl-1H-pyrazol-5-amine (159 mg, 1 mmol). The reaction mixture was reflux at ethanol temperature for 1 h. The reaction mixture was allowed to cool to room temperature. Now, the precipitated product was collected by vacuum filtration, washed with ethanol (3 mL) and then recrystallized from acetone to afford pure compound 8a as in 390 mg, 93 % yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With 1-butyl-3-methylimidazolium hydroxide; In water; at 20.0℃; for 7.0h;Green chemistry; | General procedure: A mixture of 2-iodophenol 1 (2.0 mmol), tetronic acid 2 (2.0 mmol), water 3 ml and [bmIm]OH (10 mol%) was stirred at room temperature for 5 h. After completion of reaction as indicated by TLC, 20 mL of water was added to the reaction mixture and stirred well. The product was extracted with EtOAc (3 * 20 mL). The combined organic layer were dried over anhydrous Na2SO4 to afford the crude product and recrystallized from ethanol to obtain analytically pure compound 4 (75-90%). After isolation of the product, the remaining aqueous layer containing the ionic liquid was washed with ether (2x10 mL) to remove organic impurity and filtered. The filtrate was extracted with dichloro methane (2 * 10 mL), dried over MgSO4 and evaporated under reduced pressure to afford [bmIm]OH, which was reused thrice in subsequent runs without further purification. |