Structure of 625-51-4
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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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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 625-51-4 |
Formula : | C3H7NO2 |
M.W : | 89.09 |
SMILES Code : | CC(NCO)=O |
MDL No. : | MFCD00014417 |
InChI Key : | HWJHZLJIIWOTGZ-UHFFFAOYSA-N |
Pubchem ID : | 69365 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 6 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.67 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 20.7 |
TPSA ? Topological Polar Surface Area: Calculated from |
49.33 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.88 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-1.05 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-0.93 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-1.25 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.8 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
-0.63 |
Log S (ESOL):? ESOL: Topological method implemented from |
0.4 |
Solubility | 224.0 mg/ml ; 2.52 mol/l |
Class? Solubility class: Log S scale |
Highly soluble |
Log S (Ali)? Ali: Topological method implemented from |
0.5 |
Solubility | 283.0 mg/ml ; 3.18 mol/l |
Class? Solubility class: Log S scale |
Highly soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
0.0 |
Solubility | 89.5 mg/ml ; 1.0 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 |
-7.59 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) |
1.0 |
* 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 potassium hydroxide; In 1,4-dioxane; water; at 25 - 70℃; | Add the compound of formula (H) (5.62 mmol)And KOH (0.66mmol) in 20mL H2O / dioxane (1: 3v / v) mixed solution,To the above mixed solution was added formaldehyde (35% aqueous solution, 8.43mmol),The reaction solution was reacted at 70 C for 5 min, and then cooled to 25 C and stirred overnight.Adjust the pH to 7 with 1N HCl,Concentrated under reduced pressure. The residue was dissolved with acetone,Dry over anhydrous sodium sulfate, filter, and concentrate,To a compound of formula (G),Used directly in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In a round-bottom f[ask equipped with a mechanica[ stirrer, a thermometer and a condenser 3.56 g (40 mmo[e) N-hydroxymethy[acetamide was mixed with 10 m[ acetonitri[e. S[ow[y, 2.20 g (10 mmo[e) P406 was added. Afterwards the reaction mixture was heated to 80 C for 1 hour. Then 0.15 g (1 mmo[e)trif[uoromethanesu[fonic acid was added and stirring was continued for 2 hours at 80 C. A[[ vo[ati[es were removed in vacuum and the residue was disso[ved in 5 m[ H20 and 10 m[ NaOH so[ution (50 %w/w in H20) and heated to 100 C for 2 hours. The obtained so[ution was ana[ysed by 31P-NMR spectroscopy. Aminomethy[phosphonic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With phosphorus pentachloride; trichlorophosphate; for 2.5h;Reflux; | A compound of formula (G) (3.0 mmol) was dissolved in 10 mL of POCl3,Heat to reflux and carefully add PCl5 (6.0 mmol) in portions.The reaction was refluxed for 2.5 h, and the reaction was completed by TLC.The temperature was lowered to room temperature, and the reaction solution was poured into 200 mL of ice water. The pH of the 1NNaOH solution was adjusted to neutrality, extracted with CH2Cl2, and dried over anhydrous sodium sulfate.Filtration, concentration and purification by column chromatography provided the compound of formula (F). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trifluoroacetic acid; | 3-((acetamidomethyl)sulphanyl)propanoic acid (Acm) (IV.2) 3-mercaptopropanoic acid (1.64 ml; 19 mmol) is dissolved into trifluoroacetic acid (30 ml). <strong>[625-51-4]N-(hydroxymethyl)acetamide</strong> (1.6 g; 19 mmol) is next added. After stirring for 30 minutes at room temperature, TFA is evaporated off to obtain IV.2: HPLC tR 7.1 min. (linear gradient, 5-65% B, 20 min); 1H NMR (300 MHz, CDCl3, 298 K) delta 12.4 (s, COOH, 1H); 7.74 (d, NH, J=5.8 Hz, 1H); 4.34 (d, SCH2NH, J=6 Hz, 2H); 2.81 (t, CH2SCH2NH, J=6.4 Hz, 2H); 2.67 (t, CH2COOH, J=6.4 Hz, 2H); 2.1 (s, NHCOCH3, 3H); 13C NMR (300 MHz, CDCl3, 298 K) 177.45 (CO); 174.63 (CO); 41.60 (CH2); 34.37 (CH2); 25.67 (CH2); 21.46 (CH3). |