Structure of 808-57-1
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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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Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
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CAS No. : | 808-57-1 |
Formula : | C24H24O6 |
M.W : | 408.44 |
SMILES Code : | COC1=C(OC)C=C2C3=CC(OC)=C(OC)C=C3C4=CC(OC)=C(OC)C=C4C2=C1 |
MDL No. : | MFCD00075571 |
InChI Key : | TXROZCSFVVIBFI-UHFFFAOYSA-N |
Pubchem ID : | 4607363 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 30 |
Num. arom. heavy atoms | 18 |
Fraction Csp3 | 0.25 |
Num. rotatable bonds | 6 |
Num. H-bond acceptors | 6.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 117.91 |
TPSA ? Topological Polar Surface Area: Calculated from |
55.38 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
4.07 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.71 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
5.2 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.62 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
5.32 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
4.38 |
Log S (ESOL):? ESOL: Topological method implemented from |
-5.39 |
Solubility | 0.00167 mg/ml ; 0.0000041 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-5.6 |
Solubility | 0.00102 mg/ml ; 0.0000025 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-8.11 |
Solubility | 0.00000321 mg/ml ; 0.0000000079 mol/l |
Class? Solubility class: Log S scale |
Poorly 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) |
Yes |
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 |
-5.45 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) |
2.24 |
* 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 |
---|---|---|
90.1% | at 25℃; for 24 h; | A type B crystal of 2,3,6,7,10,11-hexahydroxytriphenylene monohydrate was synthesized according to the process described in Synthesis, 477, 1994 and JP-A-8-119894. Namely, 1,2-dimethoxybenzene (31.78 g, 0.23 moles) and anhydrous ferric chloride (120 g, 0.74 moles) were dissolved in 70percent sulfuric acid, and the solution was reacted at 25°C for 24 hours with stirring. After completion of the reaction, the solution was poured into ice water (500 g), and the precipitated crystal was collected by filtration. After the resultant crystal was washed with water (1 L), and then dried to give pale purple colored 2,3,6,7,10,11-hexamethoxytriphenylene (28.2 g, theoretical yield from 1,2-dimethoxybenzene: 90.1percent) (the method of Synthesis, 477, 1994). |
85.4% | at 10 - 15℃; for 6 h; | 600 ml of ethyl acetate was added into a 1000ml four-necked flask, sodium peroxydisulfate 102.4g (0.43 mol) and o-xylene 45.7 g (0.43 mol) were added, stirred and cooled at internal temperature of 10 degrees C. Anhydrous iron(III) chloride 345.4g (2.10 mol) was added little by little, reacted at an internal temperature of 10-15 degrees C for 6 hours. After completion of the reaction, reaction mixture was cooled, 2000 ml of water was added and stirred for 10minutes. The aqueous layer of the solution was separated, and the organic layer was washed with 800 ml of salt solution. 600 ml of methanol was added to the organic layer and crystallized at 15-25 degrees C for 1 hour, the crystals were filtered, and dried to obtain 19.5 g (43.6percent of yield) of objects as gray crystal. |
82% | With trifluorormethanesulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane at 20℃; for 10 h; Inert atmosphere | General procedure: An oven-dried 20 mL scintillation vial, equipped with a magnetic stir-bar, was charged with the starting material (1.0 equiv), DDQ (1.0 equiv), trifluoromethanesulfonic acid (1.4percent v/v, 3.0 equiv), and 1,2-dichloroethane (0.05 M). The reaction mixture was then allowed to stir at ambient temperature for 10 h. After this time, methanol (0.05M) was added, and the solution was then allowed to stir at ambient temperature for an additional hour. Upon addition of the methanol, some solids precipitated out of the solution. Then, the solvent was removed from the heterogeneous mixture under reduced pressure. The crude material was purified by either recrystallization (methanol/DCM) or silica-gel column chromatography (hexanes/DCM) to give the title compounds. |
80% | With iron(III) chloride; sulfuric acid In dichloromethane at 20℃; for 3 h; | A solution of 1,2-dimethoxybenzene (10 g, 72.4 mmol) in dichloromethane(50 ml) was added dropwise to a suspension of anhydrous FeCl3 (35.22 g, 217.2 mmol) in dichloromethane (100 ml) and concentrated sulphuric acid (0.5 ml). After complete addition (15 min), the reaction mixture was further stirred for 3 h at room temperature. 200 ml of methanol were then slowly added under vigorous stirring. The obtained mixture was further stirred for additional 30 min. And the precipitate was filtered off, washed with methanol (5 × 100 ml) and dried under reduced pressure to give a purple solid. Yield: 80percent, 1HNMR (CDCl3) δ/ppm: 4.10 (s, 18H, OCH3), 7.80 (s, 6H, ArH). |