Structure of Boc-Trp-OH
CAS No.: 13139-14-5
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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. : | 13139-14-5 |
Formula : | C16H20N2O4 |
M.W : | 304.34 |
SMILES Code : | O=C(O)[C@H](CC1=CNC2=CC=CC=C12)NC(OC(C)(C)C)=O |
MDL No. : | MFCD00065595 |
InChI Key : | NFVNYBJCJGKVQK-ZDUSSCGKSA-N |
Pubchem ID : | 83169 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 22 |
Num. arom. heavy atoms | 9 |
Fraction Csp3 | 0.38 |
Num. rotatable bonds | 7 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 3.0 |
Molar Refractivity | 83.2 |
TPSA ? Topological Polar Surface Area: Calculated from |
91.42 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.68 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.97 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.69 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.37 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.28 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.0 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.81 |
Solubility | 0.473 mg/ml ; 0.00155 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.52 |
Solubility | 0.0929 mg/ml ; 0.000305 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.05 |
Solubility | 0.0272 mg/ml ; 0.0000893 mol/l |
Class? Solubility class: Log S scale |
Moderately 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) |
Yes |
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 |
0.0 |
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<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.94 |
* 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 |
---|---|---|
General procedure: All protected amino acids were coupled in CH2Cl2 (5 ml) using DCC (2.5 equiv.) and HOBt (2.5 equiv.) until completion (3 h) judged by Kaiser [15] ninhydrin test. After coupling of the appropriate amino acid, Boc deprotection was effected by use of TFA/CH2Cl2 (1:1, 5 ml)) for 5 min first then repeated for 25 min. Following neutralization with 10% TEA/CH2Cl2 three times (5-5 ml of each), the synthetic cycle was repeated to assemble the resin-bond protected peptide. The peptides were cleaved from the resin with simultaneous side chain deprotection by acidolysis with anhydrous hydrogen fluoride (5 ml) containing 2% anisole, 8% dimethyl sulfide and indole at 5 C for 45 min. The crude peptides were dissolved in aqueous acetic acid and lyophilized. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.1 g | With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; for 1.16667h;Cooling with ice; | Example 2Boc-L-Trp-L-Arg-OMe (KP-3-2)To a stirred solution of Boc-L-Trp-OH (761 mg, 2.5 mmoles), H-L-Arg-OMe dihydrochloride (718 mg, 2.75 mmoles), HOBt (1378 mg, 9 mmoles) and DIPEA (2.05 ml, 12 mmoles) in DMF (5 ml) and dichloromethane (2 ml) cooled on ice was added HBTU (1138 mg, 3 mmoles) in small portions over 10 minutes. The mixture was stirred on ice for 1 hour, 40 ml ethyl acetate was added and the organic phase washed successively with 3×40 ml saturated NaHCO3, 2×30 ml 5% citric acid, 50 ml water and 2×30 ml brine. Evaporation afforded 1.1 g of a white solid |
A321815 [112525-72-1]
2-((tert-Butoxycarbonyl)amino)-3-(1H-indol-3-yl)propanoic acid
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