Structure of 15206-55-0
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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. : | 15206-55-0 |
Formula : | C9H8O3 |
M.W : | 164.16 |
SMILES Code : | O=C(OC)C(C1=CC=CC=C1)=O |
MDL No. : | MFCD00008443 |
InChI Key : | YLHXLHGIAMFFBU-UHFFFAOYSA-N |
Pubchem ID : | 84835 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.11 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 42.73 |
TPSA ? Topological Polar Surface Area: Calculated from |
43.37 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.84 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.66 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.04 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.02 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.57 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.43 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.08 |
Solubility | 1.38 mg/ml ; 0.0084 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.18 |
Solubility | 1.07 mg/ml ; 0.00654 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.41 |
Solubility | 0.634 mg/ml ; 0.00386 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 |
-6.12 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 |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 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) |
1.29 |
* 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 hydrogen;chloro(1,5-cyclooctadiene)rhodium(I) dimer; C40H58FeN2O3P2; In toluene; at 25℃; under 60006.0 Torr; for 23h;Product distribution / selectivity; | The catalyst precursor and the ligand were stirred in the solvent under argon. A solution of the substrate was added, the argon is drawn off with vacuum and the vessel is connected to a hydrogen supply at the given pressure and temperature. Switching on the stirrer starts the hydrogenation. After the given time, the stirrer is switched off and the solution is placed under argon again. Conversion and enantiomeric excess (ee) are determined by gas chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | General procedure: To a stirred solution of 1a (0.36 g, 2.0mmol) in THF (5 mL) at ?78 C was added n-BuLi (1.6 M in hexane; 4.0 mmol) dropwise. After 15 min,temperature was raised to 0 C and stirring was continued for 2.5 h. Then, the mixture was cooled to ?78C and MeCOCO2Me (0.20 g, 2.0 mmol) was added dropwise. The resulting mixture was graduallywarmed to 0 C, treated with saturated aqueous NH4Cl (20 mL), and extracted with AcOEt (3 × 15 mL).The combined extracts were washed with brine (15 mL), dried (Na2SO4), and concentrated by evaporation.The residue was purified by column chromatography on SiO2 (AcOEt/hexane 1:3) to afford 2a (0.28 g,50percent); |