Structure of 1124-29-4
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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. : | 1124-29-4 |
Formula : | C7H7NO2 |
M.W : | 137.14 |
SMILES Code : | CC(C1=CC=C(O)N=C1)=O |
MDL No. : | MFCD10697705 |
InChI Key : | OMNAPXPEWSOPER-UHFFFAOYSA-N |
Pubchem ID : | 15882189 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 36.45 |
TPSA ? Topological Polar Surface Area: Calculated from |
50.19 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.13 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.51 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.99 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.08 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.17 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.75 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.39 |
Solubility | 5.59 mg/ml ; 0.0408 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.13 |
Solubility | 10.1 mg/ml ; 0.0734 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.76 |
Solubility | 2.41 mg/ml ; 0.0175 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 |
-6.77 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 |
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) |
1.43 |
* 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 |
---|---|---|
In acetic anhydride; for 64.0h;Reflux; | Step 2: 3-Acetyl-lH-pyridin-2-one and 5-acetyl-lH-pyridin-2-one[00182] A suspension of 1 -( 1 -oxidopyridin- 1 -ium-3 -yl)ethanone (1.93 g, 14.0 mmol) in acetic anhydride (21.6 mL, 229 mmol) was heated at reflux for 64 hours. The solvent was evaporated under reduced pressure and the crude residue was dissolved in ethyl acetate. Silica gel was added and the slurry was stirred. The slurry was filtered using ethyl acetate and the filtrate was evaporated under reduced pressure to give a mixture of 3-acetylpyridin-2(lH)- one and 5-acetylpyridin-2(lH)-one. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | With pyrrolidine; In toluene; at 110℃; for 17.0h; | Step 2: 3-Acetyl-lH-pyridin-2-one and 5-acetyl-lH-pyridin-2-one[00182] A suspension of 1 -( 1 -oxidopyridin- 1 -ium-3 -yl)ethanone (1.93 g, 14.0 mmol) in acetic anhydride (21.6 mL, 229 mmol) was heated at reflux for 64 hours. The solvent was evaporated under reduced pressure and the crude residue was dissolved in ethyl acetate. Silica gel was added and the slurry was stirred. The slurry was filtered using ethyl acetate and the filtrate was evaporated under reduced pressure to give a mixture of 3-acetylpyridin-2(lH)- one and 5-acetylpyridin-2(lH)-one. To the mixture was added tert-butyl 4-oxopiperidine-l- carboxylate (2.78 g, 14.0 mmol), pyrrolidine (2.57 mL, 30.7 mmol) and toluene (19 mL).Molecular sieves (1 g) were added and the mixture was heated at 110 C for 17 hours. The mixture was cooled to room temperature and was filtered using ethyl acetate. The filtrate was washed with water (2 x 50 mL). The combined organics were dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure. The crude residue was purified on silica gel utilizing a gradient of 0-100% ethyl acetate in hexane to yield tert-butyl 4- oxospiro[3H-pyrano[2,3-b]pyridine-2,4'-piperidine]- -carboxylate (614 mg, 14%). ESI-MS m/z calc. 318.2, found 319.5 (M+l)+; Retention time: 1.32 minutes (3 min run). |
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