Structure of 5856-33-7
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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. : | 5856-33-7 |
Formula : | C14H14O2 |
M.W : | 214.26 |
SMILES Code : | CCCC(OC1=CC=C2C=CC=CC2=C1)=O |
MDL No. : | MFCD00046464 |
InChI Key : | KCWQXDQUKLJUEU-UHFFFAOYSA-N |
Pubchem ID : | 347991 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 16 |
Num. arom. heavy atoms | 10 |
Fraction Csp3 | 0.21 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 65.06 |
TPSA ? Topological Polar Surface Area: Calculated from |
26.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.58 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.56 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.55 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.45 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.56 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.34 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.61 |
Solubility | 0.0526 mg/ml ; 0.000246 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.8 |
Solubility | 0.0341 mg/ml ; 0.000159 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.97 |
Solubility | 0.00232 mg/ml ; 0.0000108 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) |
Yes |
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) |
Yes |
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 |
-5.08 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<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.68 |
* 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 |
---|---|---|
General procedure: Kobayashi silylaryl triflate 1 (0.68 mmol) and aliphatic carboxylic acid 2 (3.4 mmol) in acetonitrile(4.0 mL) was added sodium hydroxide (80 mg, 2.0 mmol) under nitrogen atmosphere. After stirringfor 10 minutes at room temperature, cesium fluoride (410 mg, 2.7 mmol) was then introduced. Themixture was stirred at 80 oC for 4 h. After removal of the solvent, the residue was then purified byflash column chromatography on silica gel (eluent = petroleum ether/ethyl acetate 10:1 v/v) to givethe desired product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
106.9 mg | With sodium carbonate; In acetonitrile; at 120℃; for 24h;Schlenk technique; | General procedure: A mixture of phenol 1 (0.50 mmol), Na2CO3 (10.6 mg, 0.10mmol, 20 mol%), and alkenyl carboxylate (2.0 mmol, 4.0 equiv)in MeCN (3 mL) was added to a Schlenk flask (25 mL) and stirredat r.t. The mixture was stirred at 120 C until the reaction wasfinished. Then, the solvent was evaporated under reduced pressureand the residue was purified by column chromatography(petroleum ether/ethyl acetate 20:1 to 10:1) to afford theproduct 3. |
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