Structure of 606-23-5
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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'.
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CAS No. : | 606-23-5 |
Formula : | C9H6O2 |
M.W : | 146.14 |
SMILES Code : | O=C1CC(C2=C1C=CC=C2)=O |
MDL No. : | MFCD00003779 |
InChI Key : | UHKAJLSKXBADFT-UHFFFAOYSA-N |
Pubchem ID : | 11815 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.11 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 39.91 |
TPSA ? Topological Polar Surface Area: Calculated from |
34.14 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.3 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.61 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.46 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.69 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.45 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.3 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.53 |
Solubility | 4.27 mg/ml ; 0.0292 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.9 |
Solubility | 18.4 mg/ml ; 0.126 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.98 |
Solubility | 0.152 mg/ml ; 0.00104 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 |
-6.76 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) |
1.27 |
* 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 |
---|---|---|
79% | In ethanol; at 50℃; for 4h; | By the adoption of the following formula 1a compound of the desired: the 1, 2, 3, 5, 6, 7-hexahydro-pyrido [3, 2, 1-ij] quinoline-9-formaldehyde (4.02g) and compound 1H-indene -1,3 (2H)-dione (2.92g) in ethanol solvent (150 ml) in 50 C stirring in the backflow 4 hours, the solid obtained from the same filter, the chemical purification by column chromatography, recrystallization, and a (its yield = 79%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | In butan-1-ol; at 120℃; for 2h; | General procedure: 1,3-Indandione (0.19 g, 1.3 mmol) and 4-[bis(4-methoxyphenyl)amino]benzaldehyde (a) (0.4 g 1.43 mmol) were dissolved in 22 mL of butan-1-ol and refluxed for 2 h. Then the mixture was cooled down to the room temperature. The solid precipitate was collected and recrystallized from butan-1-ol to give 0.53 g of red crystals (65percent yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | General procedure: In a round bottomed flask, indane-1,3-dione (1 mmol) was dissolvedin pyridine (5 mL) and stirred for 5-10 min. Then substituted benzaldehyde(1 mmol) was added and the reaction mixture was refluxed for1 h at 100 C. The reaction progress was monitored by TLC. Aftercompletion, the reaction mixture was brought to room temperature andthen poured onto ice cold water. The resulting precipitates were filteredand washed thoroughly with hexane. The precipitates were crystallizedfrom methanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With L-proline; In methanol; at 20℃; | General procedure: A solution of 1,3-indanedione (5 mmol, 1eq), substituted salicylaldehyde (5 mmol, 1eq) and L-proline ( 30 mol%, 1.5 mmol, 0.3eq) in methanol (15ml) was stirred at room temperature until a precipitate formed. The formed precipitate was filtered and washed several times with methanoland diethyl ether to afford the 2-hydoxybenzylidineindenediones. The products were used for the next step without further purification. |