Structure of 91-52-1
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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. : | 91-52-1 |
Formula : | C9H10O4 |
M.W : | 182.17 |
SMILES Code : | C1=C(OC)C=CC(=C1OC)C(O)=O |
MDL No. : | MFCD00002434 |
InChI Key : | GPVDHNVGGIAOQT-UHFFFAOYSA-N |
Pubchem ID : | 7052 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.22 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 46.39 |
TPSA ? Topological Polar Surface Area: Calculated from |
55.76 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.51 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.1 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.4 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.06 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.23 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.26 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.81 |
Solubility | 2.85 mg/ml ; 0.0156 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.86 |
Solubility | 2.49 mg/ml ; 0.0137 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.03 |
Solubility | 1.72 mg/ml ; 0.00942 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 |
-6.63 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) |
1.49 |
* 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 trichlorophosphate; | Example 2 8-(2,4-Dimethoxy-phenyl)-purine A mixture of 5.5 g of <strong>[13754-19-3]4,5-diaminopyrimidine</strong> and 10.9 g of 2,4-dimethoxy-benzoic acid was triturated in a mortar. The mixture was added to 100 ml of phosphorus oxychloride and refluxed for one hour. The phosphorus oxychloride was decomposed under stirring into water, and the solution obtained was neutralized with ammonia after filtration. The precipitated product was recrystallized from water and ethanol/cyclohexane (volume ratio of 1:3). Yield: 3.5 g (27% of theory), M.P.: 218-220 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With PPA; In methoxybenzene; | Step 6a: 2,4,4'-trimethoxybenzophenone. To a reaction flask were added 5.0 g (0.030 mole) of 2,4-dimethoxybenzoic acid, 3.25 g (0.030 mole) of anisole and 30 g of polyphosphoric acid. The reaction mixture was warmed to 60-70C with stirring for 2 hours and transferred into ice water. The resulting oil was extracted with ethyl acetate, the organic layer was separated, dried, evaporated and the resulting crude product was purified by column chromatography on silica using a 4:1 mixture of toluene and ethyl acetate as eluent. A light-yellow powder (3.5 g, 43%) was produced. |
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