Structure of 519032-08-7
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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. : | 519032-08-7 |
Formula : | C17H19N3O6 |
M.W : | 361.35 |
SMILES Code : | O=C(C1=NC(C(C)(NC(OCC2=CC=CC=C2)=O)C)=NC(O)=C1O)OC |
MDL No. : | MFCD12026362 |
InChI Key : | NIVUTAZNLHLBAN-UHFFFAOYSA-N |
Pubchem ID : | 135446261 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 26 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.29 |
Num. rotatable bonds | 8 |
Num. H-bond acceptors | 8.0 |
Num. H-bond donors | 3.0 |
Molar Refractivity | 90.4 |
TPSA ? Topological Polar Surface Area: Calculated from |
130.87 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.75 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.2 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.58 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.52 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.26 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.66 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.28 |
Solubility | 0.19 mg/ml ; 0.000525 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.58 |
Solubility | 0.00945 mg/ml ; 0.0000262 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.02 |
Solubility | 0.0347 mg/ml ; 0.0000959 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 |
No |
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 |
-6.94 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<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
3.32 |
* 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 |
---|---|---|
58% | Stage #1: at 20℃; for 2 h; Stage #2: With xylene In methanol at 90 - 120℃; for 16 h; Inert atmosphere |
Benzyl 2-amino-2-(hydroxyimino)-1,1-dimethylethylcarbamate (2.0 g, 8.0 mmol) was dissolved in 30 mL MeOH, dimethyl acetylenedicarboxylate (DMAD, 1.1 mL, 9.0 mmol) was added slowly. The mixture was stirred for 2 h at room temperature, and then concentrated under reduced pressure to give a white oil. The mixture of the oil and 80 mL xylene was stirred at 90 °C for 2 h and 120 °C for 2 h, then refluxed for 12 h under nitrogen, concentrated to yield the crude product. The crude product was recrystallized with 2 mL MeOH and 10 mL tert-butyl methyl ether to afford 5 as a yellow solid (1.7 g, 58 percent): 1H-NMR (DMSO-d6) δ: 7.35 (m, 5H), 5.00 (s, 2H), 3.83 (s, 3H), 1.48 (s, 6H); ESI-MS m/z 360 (M)-, 384 (M+Na) +. |
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