Structure of H-DL-Trp(7-Cl)-OH
CAS No.: 153-97-9
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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. : | 153-97-9 |
Formula : | C11H11ClN2O2 |
M.W : | 238.67 |
SMILES Code : | O=C(O)C(N)CC1=CNC2=C1C=CC=C2Cl |
MDL No. : | MFCD09264324 |
InChI Key : | DMQFGLHRDFQKNR-UHFFFAOYSA-N |
Pubchem ID : | 643956 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H317 |
Precautionary Statements: | P280 |
Num. heavy atoms | 16 |
Num. arom. heavy atoms | 9 |
Fraction Csp3 | 0.18 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 3.0 |
Molar Refractivity | 62.37 |
TPSA ? Topological Polar Surface Area: Calculated from |
79.11 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.46 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.43 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.78 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-1.11 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.17 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.77 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.27 |
Solubility | 12.9 mg/ml ; 0.0541 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.77 |
Solubility | 40.9 mg/ml ; 0.171 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.37 |
Solubility | 0.101 mg/ml ; 0.000423 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 |
-8.06 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 |
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) |
2.25 |
* 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 |
---|---|---|
With hydrogenchloride; In water; at 100℃; for 6.0h; | (S)-7'-Chlorotryptophan, 3. Method A: (S)-N-acetyl-7'-chlorotryptophan was refluxed in 3 N HCl for 6 h to remove the acetyl group. Concentration of the reaction mixture gave x mg of (S)-7'-chlorotryptophan ( %). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.4%Chromat.; 4.5%Chromat. | With disodium hydrogenphosphate; Rhodococcus ruber alcohol dehydrogenase; flavin reductase PrnF; tryptophan 6-halogenase from Streptomyces albogriseolus RebH5 variant; NAD; flavin adenine dinucleotide; sodium chloride; In isopropyl alcohol; at 25℃; for 86.0h;pH 7.4;Enzymatic reaction; | Enzymatic chlorination was assayed in a total volume of 500lwhileshakinggentlyat25C.Substrate L -tryptophan wasadded to a final concentration of 5 m M together with 1 m MNAD, 0.01 m M FAD, 1 unit ml 1RR-ADH, 2.5 units ml 1flavin reductase PrnF, 5% (v/v) isopropyl alcohol, 10 m MNa 2 HPO 4 , pH 7.4, and 30 m M NaCl. Purified halogenase wasadded to a final concentration of 89M . Reactions were per-formed as triplicates, and reaction progress was monitored byHPLC-MS or analytical HPLC. Aliquots of 30lweretakenfrom the reaction mixture at different time points andquenched by adding an equal volume of methanol. The mixturewas centrifuged (12,000 g, 10 min), and the supernatant wasanalyzed via HPLC-MS or analytical HPLC. |