Structure of 13096-31-6
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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. : | 13096-31-6 |
Formula : | C6H11NO3 |
M.W : | 145.16 |
SMILES Code : | O=C(C1NCC(O)CC1)O |
MDL No. : | MFCD08694639 |
InChI Key : | RKEYKDXXZCICFZ-UHFFFAOYSA-N |
Pubchem ID : | 151730 |
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 | 0 |
Fraction Csp3 | 0.83 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 3.0 |
Molar Refractivity | 38.49 |
TPSA ? Topological Polar Surface Area: Calculated from |
69.56 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.81 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-2.81 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-1.2 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-3.07 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.44 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
-1.34 |
Log S (ESOL):? ESOL: Topological method implemented from |
1.1 |
Solubility | 1810.0 mg/ml ; 12.5 mol/l |
Class? Solubility class: Log S scale |
Highly soluble |
Log S (Ali)? Ali: Topological method implemented from |
1.9 |
Solubility | 11600.0 mg/ml ; 80.2 mol/l |
Class? Solubility class: Log S scale |
Highly soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
0.36 |
Solubility | 336.0 mg/ml ; 2.32 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 |
-9.18 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 |
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) |
2.31 |
* 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 |
---|---|---|
100% | With 10 wt% Pd(OH)2 on carbon; hydrogen; In methanol; water; at 65.0℃; under 26252.6 Torr; for 24.0h;Autoclave; | The compound XII (350.00g, 2 . 516 muM, 1 . 0eq.) soluble in water/methanol (5L/1L) in, addingPd (OH) 2/C(50.00g),put into the autoclave, accessH2(3.5MPa),65Creaction 24h. LC - Ms detecting raw material disappears, the locating, filtering, the filtrate is concentrated with toluene several times and for water gets brown liquid 365.22g, directly cast a step, the yield (theoretical): 100%. |
With palladium 10% on activated carbon; hydrogen; acetic acid; In water; at 50.0℃; under 2585.81 Torr; for 12.0h; | To a solution of 410 5-hydroxypyridine-2-carboxylic acid (60 g, 431 mmol, 1 eq.) in 411 AcOH (200 mL)/53 H2O (600 mL) was added wet 412 Pd/C (2 g, 10% content) under N2. The suspension was degassed under vacuum and purged with H2 several times. The mixture was stirred under H2 (50 psi) at 50 C. for 12 hrs, then filtered and concentrated to give 413 5-hydroxypiperidine-2-carboxylic acid (62.61 g, crude) as a yellow oil. ESI [M+H]=146.5 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 23 1-(3-Mercaptopropanoyl)-5-Hydroxy-L-Pipecolic Acid By substituting <strong>[13096-31-6]5-hydroxy-L-pipecolic acid</strong> for L-proline in procedure of Example 13 and then treating the product by the Procedure A of Example 18, 1-(3-benzoylthiopropanoyl)-5-hydroxy-L-pipecolic, and 1-(3-mercaptopropanoyl)-<strong>[13096-31-6]5-hydroxy-L-pipecolic acid</strong> are obtained. | ||
EXAMPLE 23 1-(3-Mercaptopropanoyl)-5-Hydroxy-L-Pipecolic Acid By substituting <strong>[13096-31-6]5-hydroxy-L-pipecolic acid</strong> for L-proline in the procedure of Example 13 and then treating the product by the Procedure A of Example 18, 1-(3-benzoylthiopropanoyl)-5-hydroxy-L-pipecolic, and 1-(3-mercaptopropanoyl)-<strong>[13096-31-6]5-hydroxy-L-pipecolic acid</strong> are obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride; for 2.0h;Cooling with ice; Reflux; | The upper step of the product (365.22g, 2 . 516 muM, 1 . 0eq.) dissolved in MeOH (3000 ml) in. under the ice-bath adds by dropsSOCl2(448.99g, 3.774mol, 1.5eq.)dropping process temperature can be raised to reflux, then completing, reflux 2h. LC - Ms detection reaction is complete; reducing pressure and solvent, a brown yellow liquid 489.81g, yield (theoretical): 100%. The crude product directly into the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In 1,4-dioxane; at 25.0℃; for 18.0h; | To a mixture of 413 <strong>[13096-31-6]5-hydroxypiperidine-2-carboxylic acid</strong> (62 g, 427.13 mmol, 1 eq.) and Boc2O (102.54 g, 469.84 mmol, 107.94 mL, 1.1 eq.) in 46 dioxane (500 mL) was added 358 NaOH (34.17 g, 854.25 mmol, 2 eq.) and the mixture was stirred at 25 C. for 18 hrs. The mixture was then concentrated to remove dioxane and the pH was adjusted to 2-3 by addition of 1N HCl solution. The aqueous phase was extracted with 2-Me-THF (500 mL*3). The combined organic layers was dried over Na2SO4, filtered and concentrated to give 415 1-tert-butoxycarbonyl-<strong>[13096-31-6]5-hydroxy-piperidine-2-carboxylic acid</strong> (40 g, crude) as yellow oil. ESI [M+Na]=267.9 |