Structure of 6270-46-8
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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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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 6270-46-8 |
Formula : | C5H7N3O2 |
M.W : | 141.13 |
SMILES Code : | CC1=C(N)C(O)=NC(O)=N1 |
MDL No. : | MFCD00053572 |
InChI Key : | FNSSATCDUXTALE-UHFFFAOYSA-N |
Pubchem ID : | 80453 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.2 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 3.0 |
Molar Refractivity | 35.45 |
TPSA ? Topological Polar Surface Area: Calculated from |
92.26 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.78 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.12 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-0.21 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-1.05 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.28 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
-0.18 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.08 |
Solubility | 11.6 mg/ml ; 0.0825 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.36 |
Solubility | 6.1 mg/ml ; 0.0432 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-0.51 |
Solubility | 44.1 mg/ml ; 0.313 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 |
-7.25 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 |
0.0 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) |
1.95 |
* 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 |
---|---|---|
18%; 18%; 25% | With 1,4-dioxane; 2,2'-azobis(isobutyronitrile); at 60.0℃; for 3.75h; | A glass reactor was charged with 1,4-dioxane (127 ml) containing <strong>[6270-46-8]5-amino-6-methyluracil</strong> (1) (50.0 mg, 0.35 mmol), and a solution of AIBN (248.0 mg, 1.50 mmol) in 1,4-dioxane (12.6 ml). The oxidation was performed at 60 C temperature for 225 min with constant stirring and bubbling of air until complete consumption of compound 1, determined photometrically at 290 nm wavelength. 1,4-Dioxane was removed from the reaction mixture under vacuum, the residue was washed with hot benzene (5×3 ml) to remove AIBN and the products of 1,4-dioxane oxidation. A mixture of oxidation products was obtained (44.2 mg) and separated by HPLC. 5,5,6-Trihydroxy-6-methyldihydropyrimidine-2,4(1H,3H)-dione (2). Yield 25%.* White crystals, mp 122-123 C.17,21 UV spectrum, lambdamax, nm: 203. 13C NMR spectrum, delta, ppm: 19.9 (CH3); 83.2 (C-6); 88.4 (C-5); 151.8 (C-2); 172.9 (C-4). Mass spectrum, m/z (Irel, %): 215 [M+K]+ (0.4). 6-Hydroxy-6-methyldihydropyrimidine-2,4,5(3H)-trione (3). Yield 18%. White crystals.17,21 UV spectrum, lambdamax, nm: 210. 13C NMR spectrum, delta, ppm: 25.7 (CH3); 86.9 (C-6); 157.0 (C-2); 174.7 (C-4); 207.0 (C-5). Mass spectrum, m/z (Irel, %): 197 [M+K]+ (1). 6-Hydroxy-5-hydroxyimino-6-methyldihydropyrimidine-2,4(1H,3H)-dione (4). Yield 18%, pale-yellow crystalline powder, mp 136 C (decomp.). UV spectrum, lambdamax, nm: 208, 274. 1H NMR spectrum, delta, ppm: 2.16 (3, s, CH3); 5.43 (1, br. s, 1-NH); 8.46 (2, br. s, 2OH). 13C NMR spectrum, delta, ppm: 20.8 (CH3); 94.7 (C-6); 152.0 (C-4); 153.9 (C-5); 160.7 (C-2). Mass spectrum, m/z (Irel,%): 230 [M+K+H2O]+ (61). |
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