Structure of Boc-NH-PEG4-CH2CH2COOH
CAS No.: 756525-91-4
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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. : | 756525-91-4 |
Formula : | C16H31NO8 |
M.W : | 365.42 |
SMILES Code : | CC(C)(C)OC(NCCOCCOCCOCCOCCC(O)=O)=O |
MDL No. : | MFCD07781254 |
InChI Key : | YEIYIPDFZMLJQH-UHFFFAOYSA-N |
Pubchem ID : | 2756001 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 25 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.88 |
Num. rotatable bonds | 18 |
Num. H-bond acceptors | 8.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 89.65 |
TPSA ? Topological Polar Surface Area: Calculated from |
112.55 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
3.73 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.16 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.05 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.44 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.75 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.19 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.82 |
Solubility | 55.7 mg/ml ; 0.152 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.75 |
Solubility | 6.52 mg/ml ; 0.0178 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.17 |
Solubility | 0.25 mg/ml ; 0.000684 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 |
-8.64 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
1.0 |
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 |
0.56 |
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<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
3.63 |
* 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 |
---|---|---|
1.4 g | Example 33. Bis(piperidineazepino)-6-((2-(2-(2-(2-(6-carboxyamido-2- cyanobenzothiazolyl)ethoxy)ethoxy)ethoxy)ethyl)carbamoyl)rhodamine (PBI 5122) [00194] To a solution of t-boc-N-amido-dPEG®4-acid (Quanta BioDesign, lg) and N- methylmorpholine (0.3 mL) in THF (25 mL), isobutyl chloroformate (0.36 mL) was added. After stirring for 30min, <strong>[7724-12-1]6-amino-2-cyanobenzothiazole</strong> (White et. al., J. Am. Chem. Soc. 88, 2015 (1966), 0.48g) was added, and the reaction stirred overnight. The reaction was then filtered, and the eluent concentrated. The crude reaction purified over silica gel (gradient of MeOH in CH2C12) to provide a clear oil (1.4 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.227 g | Synthesis of linker-drugReferring to the scheme of synthesis of Compound O, β-alanine was treated with maleic anhydride in DMF and the acid so obtained was reacted with N-hydroxysuccinimide (NHS) under DCC coupling to give NHS-ester. The BOC protective group in commercially available t-boc-N-amido-dPEG4-acid was removed by treatment with TFA to give the TFA salt of the amine, which was reacted with previously synthesized NHS ester. The carboxylic acid so obtained was isolated and was coupled with N-hydroxysuccinimide using EDCI to furnish NHS ester Compound O. |
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