Structure of 502764-52-5
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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. : | 502764-52-5 |
Formula : | C14H12O4S3 |
M.W : | 340.44 |
SMILES Code : | O=C(C(S1)=CC2=C1C3=C(C=C(C(OCC)=O)S3)S2)OCC |
MDL No. : | MFCD23103811 |
InChI Key : | SXBIAKZMSXMKTA-UHFFFAOYSA-N |
Pubchem ID : | 11290764 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 21 |
Num. arom. heavy atoms | 11 |
Fraction Csp3 | 0.29 |
Num. rotatable bonds | 6 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 87.26 |
TPSA ? Topological Polar Surface Area: Calculated from |
137.32 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
3.58 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.92 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
4.53 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.06 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
6.51 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
4.52 |
Log S (ESOL):? ESOL: Topological method implemented from |
-5.04 |
Solubility | 0.00309 mg/ml ; 0.00000908 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-7.54 |
Solubility | 0.00000981 mg/ml ; 0.0000000288 mol/l |
Class? Solubility class: Log S scale |
Poorly soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.49 |
Solubility | 0.0111 mg/ml ; 0.0000327 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
Low |
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) |
Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
Yes |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
Yes |
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 |
-4.88 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 |
1.0 |
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<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
3.06 |
* 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 |
---|---|---|
70.9% | With potassium carbonate; In N,N-dimethyl-formamide; for 72.0h; | 187.6 g (0.630 mol) of the compound represented by the formula 3-b obtained from the above reaction formula 16 and 5.8 L of N, N-dimethylformamide were added to a 10 L round bottom flask, and 226.3 g (1.637 mol) of potassium carbonate was added 155.1 g (1.291 mol) of ethyl 2-mercaptoacetate was added thereto, followed by stirring for 3 days. The reaction mixture was poured into water and extracted with methylene chloride. The organic layer was separated, concentrated under reduced pressure, and dried to obtain 152.0 g (70.9%) of the compound represented by the formula (3-c). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88.2% | With lithium hydroxide; In tetrahydrofuran; water; for 6.5h;Reflux; | 152.0 g (0.446 mol) of the compound represented by the formula 3-c obtained from the above reaction formula 17 and 2.3 L of tetrahydrofuran were added to a 5 L round bottom flask, and then 95.5 g (2,277 mol) of lithium hydroxide was dissolved in 2.3 L of water, The reaction mixture was stirred for 30 minutes and then refluxed for 6 hours. After the temperature was lowered to room temperature, 3 L of 1 N hydrochloric acid was poured, and the solid was filtered, washed with methanol and dried to obtain 112.0 g (88.2%) of the compound represented by the formula 3-d. |
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