Structure of 90357-51-0
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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. : | 90357-51-0 |
Formula : | C12H9F3N2O2 |
M.W : | 270.21 |
SMILES Code : | O=C(C1(C)OC1)NC2=CC=C(C#N)C(C(F)(F)F)=C2 |
MDL No. : | MFCD08460201 |
InChI Key : | UQUQTWDUTIAAAY-UHFFFAOYSA-N |
Pubchem ID : | 10149314 |
GHS Pictogram: |
![]() ![]() |
Signal Word: | Warning |
Hazard Statements: | H302+H312+H332-H315-H319-H341 |
Precautionary Statements: | P261-P201-P264-P280-P302+P352+P312-P304+P340+P312 |
Num. heavy atoms | 19 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.33 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 6.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 59.09 |
TPSA ? Topological Polar Surface Area: Calculated from |
65.42 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.01 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.58 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.27 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.18 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.12 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.23 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.48 |
Solubility | 0.894 mg/ml ; 0.00331 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.56 |
Solubility | 0.736 mg/ml ; 0.00273 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.04 |
Solubility | 0.0248 mg/ml ; 0.0000916 mol/l |
Class? Solubility class: Log S scale |
Moderately 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) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
Yes |
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 |
-6.83 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 |
0.0 |
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<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.43 |
* 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 |
---|---|---|
40% | General procedure: To a mixture of NaH (60percent in mineral oil, 0.050 g, 1.23 mmol) in anhydrous THF (2 mL) at 0 °C under Ar atmosphere was added a solution of the differently substituted phenol or thiophenol (1.11 mmol) in 1 mL of anhydrous THF. This mixture was stirred at r.t. for 20 min. A solution of the different intermediate 17-21 (0.74 mmol) in anhydrous THF (3 mL) was added slowly. The reaction mixture was stirred at r.t. o.n. The mixture was then diluted with ethyl acetate (30 mL), washed with brine (15 mL) and water (30 mL), dried over Na2SO4 and concentrated under vacuum. The crude residue was purified by flash column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | General procedure: To a mixture of NaH (60percent in mineral oil, 0.050 g, 1.23mmol) in anhydrous THF (2 mL) at 0 °C under Ar atmosphere was added a solutionof the differently substituted phenol or thiophenol (1.11 mmol) in 1 mL ofanhydrous THF. This mixture was stirred at r.t. for 20 min. A solution of thedifferent intermediate 18-23 (0.74 mmol)in anhydrous THF (3 mL) was added slowly. The reaction mixture was stirred atr.t. o.n. The mixture was then diluted with ethyl acetate (30 mL), washed withbrine (15 mL) and water (30 mL), dried over Na2SO4 andconcentrated under vacuum. The cruderesidue was purified by flash column chromatography. |
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