Structure of 198904-85-7
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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. : | 198904-85-7 |
Formula : | C17H21N3O2 |
M.W : | 299.37 |
SMILES Code : | O=C(NNCC1=CC=C(C2=NC=CC=C2)C=C1)OC(C)(C)C |
MDL No. : | MFCD04035550 |
InChI Key : | GIMJTKJSKPENNG-UHFFFAOYSA-N |
Pubchem ID : | 9796325 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 22 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.29 |
Num. rotatable bonds | 7 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 85.99 |
TPSA ? Topological Polar Surface Area: Calculated from |
63.25 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
3.04 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.78 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.13 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.16 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.47 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.71 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.39 |
Solubility | 0.122 mg/ml ; 0.000408 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.76 |
Solubility | 0.0515 mg/ml ; 0.000172 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.94 |
Solubility | 0.000345 mg/ml ; 0.00000115 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) |
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 |
-6.15 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 |
0.0 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) |
2.72 |
* 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 |
---|---|---|
Sodium iodide (12.4 g, 83 mmol) was added to 2-methyltetrahydrogen containing compound II (22.6 g, 76 mmol) at room temperatureIn furan (250 ml), after stirring for 30 minutes, a solution of compound I (24.8 g, 83 mmol mmol) in 2-methyltetrahydrofuran (350 ml) was added and stirring was continued for 30 min. Sodium hydroxide (6.1 g, 152 mmol) was added at room temperature. After stirring for 12 h, 2-methyltetrahydrofuran was removed under reduced pressure. The system was diluted with ethyl acetate (800 ml), washed twice with saturated potassium hydrogen sulfate (300 ml), washed with brine (600 ml), dried, and concentrated to give a crude product. After refluxing with ethanol/water = 1:2, the system gradually became transparent and was allowed to come to room temperature. The ethanol was evaporated under reduced pressure and the aqueous phase was extracted three times with ethyl acetate (200 ml). The organic phases were combined, dried and concentrated to give compound III. |
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