Structure of 939-89-9
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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. : | 939-89-9 |
Formula : | C10H10O2 |
M.W : | 162.19 |
SMILES Code : | OC(=O)[C@@H]1C[C@@H]1C1=CC=CC=C1 |
MDL No. : | MFCD03413442 |
Boiling Point : | No data available |
InChI Key : | AHDDRJBFJBDEPW-RKDXNWHRSA-N |
Pubchem ID : | 778516 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.3 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 45.49 |
TPSA ? Topological Polar Surface Area: Calculated from |
37.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.4 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.64 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.87 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.89 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.86 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.73 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.12 |
Solubility | 1.24 mg/ml ; 0.00764 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.04 |
Solubility | 1.49 mg/ml ; 0.0092 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.13 |
Solubility | 1.21 mg/ml ; 0.00743 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) |
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 |
-6.12 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) |
1.81 |
* 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 |
---|---|---|
i) c/s-(+/-)-2-Phenyl-cyclopropanecarboxylic acid; A solution of c/s-(+/-)-2-phenyl-cyclopropanecarboxylic acid ethyl ester (330 mg, 1.87 mmol) in MeOH (1 mL) was added to KOH (314 mg, 5.61 mmol) in MeOH (2 mL) at 0 °C. The mixture was stirred at room temperature overnight and then poured into water and extracted with CH2CI2. The organic layer was discarded and the aqueous phase was acidified with 10percent HCI and extracted with CH2CI2 (x2). The combined organic phases were dried over Na2SO4 and all volatiles were removed under EPO <DP n="75"/>vacuum. The acid was isolated as white powders and further purified by recrystallization from hexane (233 mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water; sodium hydroxide; In methanol; at 0 - 20℃; for 16h; | General procedure: Intermediate U; (Trans)-2-(pyridin-3-yl)cycloA solution of N.aOH (7.116 g in 45 mL of H20, 177.92 mmol) was added to a solution of (frans)-ethy. 2-(pyridin- 3-yl) cyclopropanecarboxylate (Intermediate T, 17 g, 88.96 mmol) in Methanol (170 mL) at 0 °C and stirred at RT for 16 h. After completion, the solvent was evaporated, the residue was diluted with water (50 mL), neutralized with Acetic acid and extracted with EtOAc (4 x 100 mL). The combined extracts were washed with water (100 mL), brine ( 100 mL), dried over anhydrous Na^SO^ filtered and evaporated to afford {trans)-2- (pyridin-3-yl)cyclopropanecarboxylic acid (9 g, 62.06 percent) as off white solid. The crude was carried to next step without further purification |
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