Structure of 69134-53-8
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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. : | 69134-53-8 |
Formula : | C9H16O5 |
M.W : | 204.22 |
SMILES Code : | O=C(OCC)C(O)CCC(OCC)=O |
MDL No. : | MFCD16620610 |
Boiling Point : | No data available |
InChI Key : | DYLHSDCNOUDICA-UHFFFAOYSA-N |
Pubchem ID : | 13270883 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.78 |
Num. rotatable bonds | 8 |
Num. H-bond acceptors | 5.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 49.11 |
TPSA ? Topological Polar Surface Area: Calculated from |
72.83 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.1 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.41 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.25 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.42 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.88 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.81 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.84 |
Solubility | 29.8 mg/ml ; 0.146 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.51 |
Solubility | 6.37 mg/ml ; 0.0312 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.13 |
Solubility | 15.1 mg/ml ; 0.0738 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 |
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<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.85 |
* 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 |
---|---|---|
33% | In tetrahydrofuran; at 0 - 20℃; for 24.0h;Inert atmosphere; | To a solution of 2-oxoglutarate ester (0.6 mmol) intetrahydrofuran (THF) (20.0 mL) at 0 C, under argonatmosphere was added NaBH4 (2.0 eq., 1.2 mmol). Themixture was stirred 24 h at room temperature and citricacid was added until the pH reaches 5-6. Then, silicagel (250 mg) was added to the reaction mixture and thesolvent was evaporated under reduced pressure. Theresidue was purified by silica gel column chromatography(EtOAc:hexane 1:1) to afford the respective alpha-hydroxyesters as a colorless oil.Diethyl 2-hydroxyglutarate (4a)Yield 33%; 1H NMR (CDCl3, 200 MHz) d 1.23 (t,J 7.7 Hz, 3H), 1.27 (t, J 7.7 Hz, 3H), 1.84-1.98 (m, 1H),2.06-2.22 (m, 1H), 2.41-2.49 (m, 2H), 3.10 (br s, 1H),4.05-4.27 (m, 5H); 13C NMR (CDCl3, 50 MHz) d 14.1, 29.3,29.7, 60.5, 61.8, 69.5, 173.1, 174.6; IR (film) n / cm-1 3500,2954, 1732, 1440, 1215, 1107; GC (FID) tR (R): 41.3 minand tR (S): 41.8 min; TLC (EtOAc:hexane 1:1) Rf = 0.40. |
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