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Structure of 6-Bromohexanoic acid
CAS No.: 4224-70-8
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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. : | 4224-70-8 |
Formula : | C6H11BrO2 |
M.W : | 195.05 |
SMILES Code : | O=C(O)CCCCCBr |
MDL No. : | MFCD00004422 |
InChI Key : | NVRVNSHHLPQGCU-UHFFFAOYSA-N |
Pubchem ID : | 20210 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H314 |
Precautionary Statements: | P280-P305+P351+P338-P310 |
Class: | 8 |
UN#: | 3261 |
Packing Group: | Ⅱ |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.83 |
Num. rotatable bonds | 5 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 40.6 |
TPSA ? Topological Polar Surface Area: Calculated from |
37.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.71 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.03 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.03 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.79 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.58 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.63 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.37 |
Solubility | 8.35 mg/ml ; 0.0428 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.4 |
Solubility | 7.71 mg/ml ; 0.0395 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.13 |
Solubility | 1.43 mg/ml ; 0.00735 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 |
Yes |
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 |
-6.76 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 |
0.56 |
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) |
2.19 |
* 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 |
---|---|---|
0.37 g | suspension of 1,38 g (1,0 mmol) of 8-((4-methoxyphenyl)(phenyl)(p- polystyryl)methylthio)octanoic acid in 10 ml DMF were treated twice with 140 mg HOBt and 125 mg DIC. The obtained resin was washed 5X with 6 ml DMF and filtered. Then a solution of <strong>[6070-59-3]tert-butyl 2-amino-3-methylbutanoate</strong> [obtained by the alkaline extraction of 420 mg (2,0 mmol) of <strong>[6070-59-3]tert-butyl 2-amino-3-methylbutanoate</strong> hydrochloride] in 4 ml DMF was added and the mixture was shacked for 3 h at RT. The resin was filtered and washed 3X DMF and 6X DCM. The resin was then treated 6Xwith 5 ml of 1,5% TFA inDCM and the combined filtrates were extracted with water and brine and the DCM solution was concentrated in the RE. The obtained oil was dissolved in 5 ml DMF and to the obtained solution 260 mg DIPEA and 195 mg 6-bromohexanoic acid in 5 ml DMF were added at 5oC. The mixture was stirred for additional 1 h at 5oC and 3 h at RT. Then 260 mg DIPEA and 254 mg 3-aminopropane-1 thiol hydrochloride (cysteaminehydrochloride) were added and the mixture was stirred for additional 2 h at RT. To the obtained DMF solution was then added EtAc and brine and the EtAc layer was extracted 3X with 5%-citric acid and water, the organic layer was dryed over anhydrous Na2SO4 and concentrated in the RE. Yield: 0,37 g of a yellowish oil (83%). |