Structure of 1817-57-8
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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. : | 1817-57-8 |
Formula : | C10H8O |
M.W : | 144.17 |
SMILES Code : | CC(C#CC1=CC=CC=C1)=O |
MDL No. : | MFCD00008776 |
InChI Key : | UPEUQDJSUFHFQP-UHFFFAOYSA-N |
Pubchem ID : | 74555 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.1 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 44.19 |
TPSA ? Topological Polar Surface Area: Calculated from |
17.07 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.11 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.2 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.71 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.31 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.52 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.17 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.52 |
Solubility | 0.432 mg/ml ; 0.003 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.19 |
Solubility | 0.925 mg/ml ; 0.00642 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.79 |
Solubility | 0.233 mg/ml ; 0.00161 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 |
-5.62 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 |
2.0 |
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) |
2.4 |
* 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 |
---|---|---|
87% | With ammonium acetate; In ethanol; at 80℃; for 3h;Microwave irradiation; | General procedure: To a solution of the dinitropyridone 1 (50 mg, 0.25 mmol) in ethanol (10 mL), 4-phenyl-3-buten-2-one (4a) (36.5 mg, 0.25 mmol) and NH4OAc (578 mg, 7.5 mmol) were added, and the resultant mixture was heated at 65 C for 24 h. After removal of the solvent, the residue was washed with benzene (3 × 10 mL) to remove unreacted ketone 4a and treated with column chromatography on silica gel (eluent: hexane/ethyl acetate =95/5) to afford 5-nitro-2-(2-phenylethenyl)pyridine (5a) (41 mg, 0.18 mmol, 72%) as a yellow powder. The reactions of the dinitropyridone 1 with other ketones 4b-f or 10a-c were performed in a similar way. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With sodium carbonate; In ethanol; at 150℃; for 1.5h;Microwave irradiation; | General procedure: an ethanolic solution of <strong>[57508-48-2]ethyl 3-amino-3-iminopropionate hydrochloride</strong> (6*HCl; 1equiv) was pretreated with Na2CO3 (1 equiv) for 10 min. After filtering, the ethynyl ketone (1.05 equiv) was added and the mixture in EtOH (3.5 mL) was irradiated at 150 C for 1.5 h (holdtime) in a pressure-rated glass tube (10 mL) using a CEM Discover microwave synthesizer by moderation of the initial magnetron power (200 W). After cooling in a flow of compressed air,the solution was immobilized on a Biotage ISOLUTE SCX-2column and eluted with EtOH-NH4OH (aq; 35%; 5:1) or ethanolic NH3 (2 M) to give the title compound. |
A146468 [1350843-85-4]
1-(2-((4-Chlorophenyl)ethynyl)phenyl)ethanone
Similarity: 0.52