Structure of 734529-57-8
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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. : | 734529-57-8 |
Formula : | C9H10N2O4 |
M.W : | 210.19 |
SMILES Code : | O=C(O)C[C@H](N)C1=CC=CC([N+]([O-])=O)=C1 |
MDL No. : | MFCD04113693 |
InChI Key : | SJBFILRQMRECCK-QMMMGPOBSA-N |
Pubchem ID : | 706689 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.22 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 5.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 54.32 |
TPSA ? Topological Polar Surface Area: Calculated from |
109.14 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.72 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-2.14 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.74 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.08 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-1.24 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
-0.37 |
Log S (ESOL):? ESOL: Topological method implemented from |
0.17 |
Solubility | 313.0 mg/ml ; 1.49 mol/l |
Class? Solubility class: Log S scale |
Highly soluble |
Log S (Ali)? Ali: Topological method implemented from |
0.38 |
Solubility | 501.0 mg/ml ; 2.39 mol/l |
Class? Solubility class: Log S scale |
Highly soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.25 |
Solubility | 11.7 mg/ml ; 0.0558 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 |
No |
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 |
-9.1 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 |
2.0 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) |
2.21 |
* 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 hydrogenchloride; In 1,4-dioxane; | 34A: (S)-ethyl 3-amino-3-(3-nitrophenyl)propanoate hydrochloride salt; [00367] (S)-3-Amino-3-(3-nitrophenyl)propanoic acid (500 mg, 2.4 mmol) was dissolved in 2.0 HCl in dioxane (2 mL) and concentrated in vacuo. In a separate flask thionyl chloride (0.21 mL, 2.8 mmol) was added to ethanol at -100C. The ethanolic solution was stirred for 20 min at -10 0C then added to the HCl salt of (S)-3~amino-3- (3-nitrophenyl)propanoic acid. The resulting solution was stirred at ambient temperature for 1 h and at 40 C for 3 h. The reaction mixture was concentrated in vacuo to yield 34A (600 mg, 92%) as a white solid. MS (ESI) m/z 239.09 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70 g | With hydrogenchloride; In ethyl acetate; at 5 - 20℃; for 2.0h; | The intermediate (V-1) (120 g) was added to ethyl acetate (200 mL).2N HCl in ethyl acetate (200 mL) was added dropwise at 5 C and stirred at room temperature for 2 h.TLC showed the reaction was complete.The organic phase was concentrated to 200 mL and then washed with water (100 ml* 2).After combining the aqueous phases, adjust the pH to 6 with 2N aqueous sodium hydroxide solution.There is a lot of solid precipitation,After filtration and drying, a pure product of the formula (I-1) is obtained.(70 g, total yield 40.3%). |
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