Structure of 17994-25-1
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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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CAS No. : | 17994-25-1 |
Formula : | C4H6O3 |
M.W : | 102.09 |
SMILES Code : | O=C(C1(O)CC1)O |
MDL No. : | MFCD00010797 |
InChI Key : | GQXURJDNDYACGE-UHFFFAOYSA-N |
Pubchem ID : | 2733160 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 7 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.75 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 22.2 |
TPSA ? Topological Polar Surface Area: Calculated from |
57.53 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.59 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.52 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-0.47 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.79 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.01 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
-0.23 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.08 |
Solubility | 85.0 mg/ml ; 0.833 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.22 |
Solubility | 61.6 mg/ml ; 0.603 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
0.58 |
Solubility | 386.0 mg/ml ; 3.78 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 |
-7.29 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 |
2.0 |
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) |
1.0 |
* 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 |
---|---|---|
With thionyl chloride; triethylamine; In methanol; | Preparation of Methyl 1-hydroxy-1-cyclopropanecarboxylate 1-Hydroxy-1-cyclopropanecarboxylic acid (587 mg, 5.75 mmol) was dissolved in methanol (20 mL) under nitrogen. Thionyl chloride (4 drops) were added and the reaction was stirred overnight at room temperature. Triethylamine was then added until the reaction was alkaline as judged by moistened pH paper. The solvent was then removed on the rotary evaporator. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.2% | With lithium hydroxide; In tetrahydrofuran; water; at 30℃; for 12h; | Compound 2 (900.0g, 7.76mol, 1.0eq) was dissolved in 9L of tetrahydrofuran and water(5: 2) into the mixed solution, then add lithium hydroxide in batches(1862.4g, 77.6mol, 10eq). The reaction solution was heated to 30 C in an oil bath and reacted for 12 hours.After the reaction is complete, cool to room temperature and adjust the pH of the reaction to 5-6 with aqueous hydrochloric acid (2N).Extract three times with ethyl acetate (3 * 5L), combine the organic phases, dry over anhydrous magnesium sulfate, filter,The organic phase was concentrated to obtain the target compound 3 (673.2g, 6.6mol),White solid, yield 85.2%. |
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