Structure of 5432-53-1
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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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CAS No. : | 5432-53-1 |
Formula : | C12H15NO |
M.W : | 189.25 |
SMILES Code : | CC(/C=C/C1=CC=C(N(C)C)C=C1)=O |
MDL No. : | MFCD00052839 |
InChI Key : | IAMOQOMGCKCSEJ-SNAWJCMRSA-N |
Pubchem ID : | 736580 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.25 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 60.55 |
TPSA ? Topological Polar Surface Area: Calculated from |
20.31 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.3 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.66 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.25 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.23 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.31 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.35 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.81 |
Solubility | 0.294 mg/ml ; 0.00155 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.74 |
Solubility | 0.346 mg/ml ; 0.00183 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.94 |
Solubility | 0.219 mg/ml ; 0.00116 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 |
Yes |
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) |
Yes |
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 |
-5.57 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 |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
1.0 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) |
2.0 |
* 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 |
---|---|---|
29.7% | With palladium 10% on activated carbon; hydrogen; In methanol; under 1551.49 Torr; for 3.0h; | General procedure: 4-Phenylbut-3-en-2-one (5 g) was dissolved in methanol (100 ml) and 10% Pd/C was added to it. The reaction mixture was shaken in a Parr shaker reactor under hydrogen pressure (30 psi) for 3 h. The reaction mixture was filtered over celite, washed with methanol (50 ml) and concentrated under reduced pressure. The crude product obtained was purified by column chromatography (Silica gel, 100-200 mesh, 9:1 hexane/ethyl acetate) to give the pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67.73% | With sodium hydroxide; In water; at 0 - 20℃; | General procedure: A solution of substituted benzaldehydes (50 mmol) in acetone (50 ml) was cooled to 0C in an ice bath. To this a 10% aqueous NaOH solution was added dropwise and the reaction mixture was allowed to attain RT. It was then stirred at room temperature till the completion of the reaction. Acetone was removed under reduced pressure and the reaction was dissolved in ethyl acetate and washed with dilute HCl. The organic layer was separated wash twice with water, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography (Silica gel, 100-200 mesh, 9:1 hexane/ethyl acetate) to give the pure product. |
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