Structure of 90064-48-5
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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. : | 90064-48-5 |
Formula : | C9H9ClO3 |
M.W : | 200.62 |
SMILES Code : | O=CC1=CC(OC)=C(Cl)C=C1OC |
MDL No. : | MFCD12964185 |
InChI Key : | VWSPFJJLIGAHLK-UHFFFAOYSA-N |
Pubchem ID : | 11008959 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.22 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 49.82 |
TPSA ? Topological Polar Surface Area: Calculated from |
35.53 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.26 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.95 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.17 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.4 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.63 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.08 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.46 |
Solubility | 0.702 mg/ml ; 0.0035 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.32 |
Solubility | 0.958 mg/ml ; 0.00478 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.22 |
Solubility | 0.12 mg/ml ; 0.0006 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 |
-6.14 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 |
0.0 |
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) |
1.7 |
* 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 hexamethylenetetramine; In chloroform; acetone; | D. 4-Chloro-2,5-dimethoxybenzaldehyde. A solution of hexamethylenetetramine (19.05 g, 136 mmol) and 4-chloro-2,5-dimethoxybromomethylbenzene (29.75 g, 112.1 mmol) in CHCl3 (119.3 mL) was refluxed for 10 min as a precipitate formed, then for 4 hours more. One-half of the solvent was removed, acetone (59.6 mL) was added, and the solution was then cooled in ice. The precipitate was collected and air-dried. The crude salt was isolated in quantitative yield and had the following physical date, mp 195-200 C. (decomp). TLC: (Acetone insoluble) IR: 2970, 2795, 1500, 1210. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With hexamethylenetetramine; In tetrahydrofuran; at 90 - 95℃; for 2.0h; | To a mixture of compound 4 (1.0 g, 5.79 mmol) and hexamethylenetetramine (893mg, 6.37 mmol) in THF, TFA (12.89 mg, 113 mmol) was added slowly. The reactionmixture was then refluxed for 2 hours. After that, the hot reaction liquid was pouredinto ice and its pH was adjusted to 7 with NaHCO3 powder. The mixture was extractedwith ethyl acetate and the organic phase was collected, washed with brine, dried overNa2SO4, and concentrated under reduced pressure to get the reaction crude. Thereaction crude was then purified with silica gel to give 543 mg compound 5 as a whitesolid in 47 % yield. |
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