Structure of 6939-11-3
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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. : | 6939-11-3 |
Formula : | C5H6N2O2S |
M.W : | 158.18 |
SMILES Code : | O=C(C(OC)=CN1)NC1=S |
MDL No. : | MFCD00094470 |
InChI Key : | CDFYFTSELDPCJA-UHFFFAOYSA-N |
Pubchem ID : | 2763759 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.2 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 38.74 |
TPSA ? Topological Polar Surface Area: Calculated from |
89.97 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.0 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.19 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.44 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.93 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.68 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.6 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.08 |
Solubility | 13.2 mg/ml ; 0.0834 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.24 |
Solubility | 9.03 mg/ml ; 0.0571 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.78 |
Solubility | 2.6 mg/ml ; 0.0164 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 |
-7.4 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 |
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) |
2.17 |
* 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 |
---|---|---|
69% | With water; nickel; for 8h;Heating / reflux; | 3.9 g of Raney nickel (slurry) are added to a hot solution of 4.1 g (0.026 mol) of 2-mercapto- 5-methoxy-3H-pyrimidin-4-one (Example P1) in 60 ml of water. After vigorous stirring for 8 hours at reflux temperature, the reaction mixture is filtered and the combined filtrates and washing fractions are concentrated by evaporation on a hot water bath. The residue obtained is recrystallised from ethanol in the presence of activated carbon. The desired target compound is obtained in a yield of 1.9 g (69 % of theory) in the form of needles having a melting point of 206-208C. 1 H NMR (300 MHz, DMSO-d6) : 7.828 ppm (s, 1H) ; 7.527 ppm (s, 1H) ; 3.728 ppm (s, 3H). |
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