Structure of 944392-68-1
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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. : | 944392-68-1 |
Formula : | C16H21BO6 |
M.W : | 320.15 |
SMILES Code : | O=C(OC)C1=CC(B2OC(C)(C)C(C)(C)O2)=CC(C(OC)=O)=C1 |
MDL No. : | MFCD11858596 |
InChI Key : | IGSNWXAGFXHYOG-UHFFFAOYSA-N |
Pubchem ID : | 42614529 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 23 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.5 |
Num. rotatable bonds | 5 |
Num. H-bond acceptors | 6.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 85.48 |
TPSA ? Topological Polar Surface Area: Calculated from |
71.06 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.0 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.61 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.56 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.4 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.78 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.47 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.33 |
Solubility | 0.149 mg/ml ; 0.000465 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.75 |
Solubility | 0.0567 mg/ml ; 0.000177 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.13 |
Solubility | 0.0238 mg/ml ; 0.0000745 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) |
Yes |
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 |
-6.4 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 |
2.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
3.34 |
* 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 |
---|---|---|
86.5% | With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In 1,3-dioxane; at 90℃; for 12h;Inert atmosphere; | IV) as shown in Figure 4:in 250 ml of the three-port are added respectively in the bottle C (4.8g, 1 . 5eq), 4-bromo-naphthalene, methyl formate (2.65g, 10mmol), K3PO4(6.4g, 30mmol), 90mL1,4-dioxane, access N230 min rear, plus four (triphenylphosphine) palladium (0.2g, mol2%), 90 C reaction 12h, distilled end of the reaction of 1,4-dioxane, diluted with water (30 ml), dichloromethane (60 ml) is extracted 3 times, collection of the lower organic layer, anhydrous Na2SO3drying, distilling solvent resulting reaction of the crude product, after drying with silica gel column chromatography (eluant: petroleum ether/ethyl acetate = 9/1) purification, bombycinous D obtained (3.26g), yield 86.5%. Melting point: 368-369C. |
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