Structure of 98-78-2
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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. : | 98-78-2 |
| Formula : | C6H8O3 |
| M.W : | 128.13 |
| SMILES Code : | O=C1CC(CC1)C(=O)O |
| MDL No. : | MFCD01320173 |
| InChI Key : | RDSNBKRWKBMPOP-UHFFFAOYSA-N |
| Pubchem ID : | 227798 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H302-H315-H319-H335 |
| Precautionary Statements: | P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 |
| Num. heavy atoms | 9 |
| Num. arom. heavy atoms | 0 |
| Fraction Csp3 | 0.67 |
| Num. rotatable bonds | 1 |
| Num. H-bond acceptors | 3.0 |
| Num. H-bond donors | 1.0 |
| Molar Refractivity | 30.81 |
| TPSA ? Topological Polar Surface Area: Calculated from |
54.37 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.7 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.43 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.44 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.11 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.74 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.27 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-0.3 |
| Solubility | 64.6 mg/ml ; 0.504 mol/l |
| Class? Solubility class: Log S scale |
Very soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-0.25 |
| Solubility | 72.6 mg/ml ; 0.567 mol/l |
| Class? Solubility class: Log S scale |
Very soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-0.26 |
| Solubility | 70.2 mg/ml ; 0.548 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 |
-7.39 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) |
2.06 |
* 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 |
|---|---|---|
| 96% | With thionyl chloride; at 15 - 20℃; | General procedure: To a solution of 3-oxocyclohexane carboxylic acid (63.0g, 0.443mol) in ethanol (950mL), SOCl2 (38.8mL, 0.532mol) was added at 15C. The reaction mixture was stirred at rt overnight, and then evaporated under reduced pressure. The residue was dissolved in CHCl3 (500mL) and stirred with saturated aq NaHCO3 (200mL) for 30min. The layers were separated, and the aqueous layer was extracted with CHCl3 (2×50mL). The combined organic phases were dried over Na2SO4 and evaporated in vacuo. The residue was distilled under reduced pressure to give 23. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 71% | With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; for 18h; | A solution of cyclopentanone-3-carboxylic acid (5.00 g, 39 mmol), caesium carbonate (12.82 g, 39 mmol) and ethyl iodide (9.12 g, 4.75 ml, 58.5 mmol) in DMF (50 ml) was stirred at RT for 18 h. The mixture was then concentrated i. vac., the residue was taken up in toluene, the mixture was concentrated again and 2 N hydrochloric acid and EtOAc were then added. The aq. phase was extracted with EtOAc (3×30 ml) and the combined organic phases were washed with aq. sodium thiosulfate soln. The organic phase was dried with Na2SO4 and concentrated i. vac.Yield: 4.34 g (71%) |
[ 98-78-2 ]
[ 785777-87-9 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 33% | With ammonium peroxydisulfate; silver nitrate; In water; acetonitrile; at 60℃; for 2h; | General procedure: Toa vial was added pyrimidine (0.42-0.65 mmol, 1.0 equiv.) (if solid), carboxylic acid (3.0 equiv.) (if solid), silver nitrate (4.0 equiv.) and ammonium persulfate (5.0equiv.). Acetonitrile (5 mL) and water(5 mL) were then added (followed by the pyrimidine and/or carboxylic acid if liquids) and the vial was capped and heated to 60 C for 2 h. The reaction mixture was monitored by TLC and LCMS. The reaction mixture was quenched by the addition of concentrated ammonium hydroxide (0.8 mL) and water (3.2 mL), diluted with brine and filtered through Celite. The filtrate was then extracted with DCM (3 x10 mL) and the organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was adsorbed onto silica and purified by flash chromatography (0-50% EtOAc in heptane) to afford the desired compound. |

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