Structure of 3923-52-2
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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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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 3923-52-2 |
Formula : | C15H12O |
M.W : | 208.26 |
SMILES Code : | C#CC(C1=CC=CC=C1)(C2=CC=CC=C2)O |
MDL No. : | MFCD00041570 |
InChI Key : | SMCLTAARQYTXLW-UHFFFAOYSA-N |
Pubchem ID : | 92976 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 16 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.07 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 64.72 |
TPSA ? Topological Polar Surface Area: Calculated from |
20.23 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.53 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.84 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.53 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.52 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.48 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.98 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.34 |
Solubility | 0.0945 mg/ml ; 0.000454 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.92 |
Solubility | 0.249 mg/ml ; 0.00119 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.48 |
Solubility | 0.00694 mg/ml ; 0.0000333 mol/l |
Class? Solubility class: Log S scale |
Moderately 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) |
Yes |
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 |
-5.55 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) |
2.36 |
* 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 |
---|---|---|
94% | A mixture of ruthenium(III)chloride hydrate (8.05 g ≈0.03 mol) and triphenylphosphane (39.3 g, 0.15 mol) wasplaced in a Schlenk flask, which was purged with argon. Methanol (300 mL) wasadded into the flask and the resulting mixture was heated at reflux for 4 h undercontinuous stirring. After cooling of the reaction mixture to rt, the precipitate wasfiltered off, washed with Et2O (3 × 100 mL) and air-dried to give 30.93 g of theWilkinson complex as black powder.Dichloro(3-phenyl-1H-inden-1-ylidene)bis(tricyclohexylphosphane)ruthenate(8). A solution of RuCl2(PPh3)3-4 (40.0 g, ≈41.7 mmol) and 1,1-diphenyl-2-propyn-1-ol(10.4 g, 50.1 mmol) in abs. THF (300 mL) was placed into a Schlenk flask under anargon atmosphere. A 5.4 M solution of HCl in dioxane (6.2 mL, 33.4 mmol) wasadded and then the mixture was heated at reflux for 30 min under continuous stirringand an argon atmosphere. After cooling to rt, around 50% of mixture volume wasevaporated under reduced pressure. Acetone (280 mL) and tricyclohexylphosphane25.7 g (91.9 mmol) were added to the residue and the resulting suspension wasstirred until thickening (≈0.5 h). After holding at -20 for 10 h the precipitate wasfiltered off and washed sequentially by methanol (2 × 80 mL), acetone (2 × 100 mL)and hexane (100 mL), then dried under vacuum at rt to give indenylidene-rutheniumcomplex 8 in 94% yield (36.3 g, 39.2 mmol) as red-brown powder.Complex 8 can be obtained by an analogical procedure in 90% yield (34.8 g)using absolute dioxane as a solvent instead absolute THF. |
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