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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. : | 3387-26-6 | 
| Formula : | C6H4O5 | 
| M.W : | 156.09 | 
| SMILES Code : | O=C(C1=COC=C1C(O)=O)O | 
| MDL No. : | MFCD00022465 | 
| InChI Key : | SYLAFCZSYRXBJF-UHFFFAOYSA-N | 
| Pubchem ID : | 76923 | 
| GHS Pictogram: |   | 
| Signal Word: | Warning | 
| Hazard Statements: | H302-H315-H319-H335 | 
| Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | 
| Num. heavy atoms | 11 | 
| Num. arom. heavy atoms | 5 | 
| Fraction Csp3 | 0.0 | 
| Num. rotatable bonds | 2 | 
| Num. H-bond acceptors | 5.0 | 
| Num. H-bond donors | 2.0 | 
| Molar Refractivity | 32.63 | 
| TPSA ? Topological Polar Surface Area: Calculated from  | 87.74 Ų | 
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from  | 0.43 | 
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by  | 0.04 | 
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from  | 0.68 | 
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from  | -0.67 | 
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by  | 0.06 | 
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions | 0.11 | 
| Log S (ESOL):? ESOL: Topological method implemented from  | -1.04 | 
| Solubility | 14.3 mg/ml ; 0.0918 mol/l | 
| Class? Solubility class: Log S scale  | Very soluble | 
| Log S (Ali)? Ali: Topological method implemented from  | -1.44 | 
| Solubility | 5.73 mg/ml ; 0.0367 mol/l | 
| Class? Solubility class: Log S scale  | Very soluble | 
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by  | -0.34 | 
| Solubility | 70.7 mg/ml ; 0.453 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 | No | 
| 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  | -7.22 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  | 0.56 | 
| 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<1.0 | 
| Synthetic accessibility? Synthetic accessibility score:  from 1 (very easy) to 10 (very difficult) | 2.33 | 
* 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 | 
|---|---|---|
| The corresponding monobenzyl esters or their sodium or potassium salts are obtained from the following dicarboxylic acid anhydrides by the above procedure. ... glutaric anhydride (refluxed in toluene overnight) cis-1,2-cyclobutanecarboxylic anhydride phthalic anhydride 1,2-naphthalenedicarboxylic anhydride 3,4-furandicarboxylic acid 2,3-pyridinedicarboxylic acid 2,3-pyrazinedicarboxylic acid | ||
| In the same manner as in Example 5 except that furan-3,4-dicarboxylic acid was used in place of cyclohexene-1,4-dicarboxylic acid, the entitled compound was prepared. Yielded amount: 2.29 g (3.26 mmol). Yield based on furan-3,4-dicarboxylic acid: 46.1 %. H-NMR (δppm, CDCl3): 1.35-1.65 (m, 18H), 2.74 (s, 12H), 2.80-3.10 (m, 8H), 4.13 (m, 2H), 5.60-5.90 (m, 8H), 8.51 (s, 2H). | 
 [ 3387-26-6 ]
                                                    
                                                    [ 3387-26-6 ]
 [ 3387-26-6 ]
                                                    
                                                    [ 3387-26-6 ]

| Yield | Reaction Conditions | Operation in experiment | 
|---|---|---|
| 92.4% | Furan-3,4-dicarboxylic acid (1) (16.7 mmol, 2.61 g)Add 30 mL of glacial acetic acid to a constant pressure dropping funnel,In a 100 mL three-necked flask with a reflux condenser and a tail gas absorption device,Warm up to 50oC and stir for 0.5 hours.Cool to room temperature.Slowly add liquid bromine (133.6 mmol, 21.4 g, 6.85 mL).After the addition was completed, the mixture was warmed to reflux and stirred overnight.Cool to room temperature and squeeze off most of the solvent under reduced pressure.Add a small amount of deionized water and slowly add sodium thiosulfate.Until the reaction no longer produces gas, filter,The filter cake was rinsed 3 times with a small amount of deionized water.The resulting solid is added to deionized water for recrystallization.Filter and dry under vacuum at 65 oC for 48 h,The object product was obtained as an off-white (4.84 g, 92.4%). The resulting solid was used in the next step without characterization. | 

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