Structure of 553-86-6
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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. : | 553-86-6 |
Formula : | C8H6O2 |
M.W : | 134.13 |
SMILES Code : | O=C1OC2=CC=CC=C2C1 |
MDL No. : | MFCD00005856 |
InChI Key : | ACZGCWSMSTYWDQ-UHFFFAOYSA-N |
Pubchem ID : | 68382 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H317-H319 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.12 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 35.99 |
TPSA ? Topological Polar Surface Area: Calculated from |
26.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.62 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.35 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.15 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.54 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.23 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.58 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.97 |
Solubility | 1.45 mg/ml ; 0.0108 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.5 |
Solubility | 4.2 mg/ml ; 0.0313 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.54 |
Solubility | 0.383 mg/ml ; 0.00286 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 |
-6.16 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) |
1.65 |
* 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 |
---|---|---|
9.1 g | With sodium tetrahydroborate; In tetrahydrofuran; at 0 - 30℃; for 5h; | (1) The reaction bottle containing the organic solvent tetrahydrofuran is cooled to 0 C, then, 1.26 g of a reducing agent sodium borohydride and 8.9 g of a benzofuranone were successively added to the reaction flask. At a heating temperature of 30 C, the reaction was carried out for 5 h, and after the reaction was completed, the reaction solution was cooled to 0 C. And adding HCl to the cooled reaction solution for quenching,Concentrated, extracted with methyl tert-butyl ether, the organic phase is then dried over anhydrous sodium sulfate, filtered, concentrated filtrate to obtain 9.1 g of 2-hydroxyphenylethanol; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With N,N,N',N'-tetramethylguanidine; In chloroform; at 20℃; for 3h;Sealed tube; | 0.20 mmol of compound 5,0.24 mmol of compound 2t,0.02 mmol TMG and 2.0 mL chloroform were added to the sealed tube, The reaction at room temperature for 3h.After removing the solvent,The residue was purified by silica gel column chromatography to give the product 6t,The yield is 92percent. |
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