Structure of Fmoc-D-Ser(Bzl)-OH
CAS No.: 122889-11-6
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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.
Synonyms: N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-(phenylmethyl)-D-serine
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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 122889-11-6 |
Formula : | C25H23NO5 |
M.W : | 417.45 |
SMILES Code : | O=C(O)[C@H](NC(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O)COCC4=CC=CC=C4 |
Synonyms : |
N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-(phenylmethyl)-D-serine
|
MDL No. : | MFCD00237032 |
InChI Key : | DYBDGLCDMLNEMJ-HSZRJFAPSA-N |
Pubchem ID : | 7019719 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 31 |
Num. arom. heavy atoms | 18 |
Fraction Csp3 | 0.2 |
Num. rotatable bonds | 10 |
Num. H-bond acceptors | 5.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 115.55 |
TPSA ? Topological Polar Surface Area: Calculated from |
84.86 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.74 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.03 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
4.04 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.82 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.98 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.52 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.74 |
Solubility | 0.00765 mg/ml ; 0.0000183 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-5.52 |
Solubility | 0.00127 mg/ml ; 0.00000305 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-7.5 |
Solubility | 0.0000133 mg/ml ; 0.0000000318 mol/l |
Class? Solubility class: Log S scale |
Poorly 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) |
Yes |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
Yes |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
Yes |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.99 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<3.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
4.31 |
* 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 |
---|---|---|
77% | With sulfuric acid; In dichloromethane; at 0℃; | Example 9. N- [ (9H-Fluoren-9-vl) methoxvcarbonyl]-O- (benzyl)-D-serine t-Butyl ester. N- [ (9H-Fluoren-9-yl) methoxycarbonyl]-O- (benzyl)-D-serine (0.710 g, 1.70 mmole) in dichloromethane (8 mL) was treated with t-butyl acetate (3 mL) and concentrated sulfuric acid (40 1L) in a sealed flask at 0 °C. Upon completion (TLC), the reaction was quenched with of dichloromethane (10 mL) and saturated aqueous potassium bicarbonate (15 mL). The organic layer was washed with distilled water, and evaporated. The resulting residue was purified by flash column chromatography (98: 2 dichloromethane/methanol) to yield the title compound as a colorless oil (0.292 g, 77percent); lH NMR (CDC13) a 1.44 (s, 9H); 3.68 (dd, J = 2.9 Hz, J = 9.3 Hz, 1H); 3.87 (dd, J = 2.9 Hz, J = 9.3 Hz, 1H); 4.22 (t, J = 7.1 Hz, 1H); 4.30-4. 60 (m, 5H) ; 5.64-5. 67 (m, 1H); 7.25- 7.39 (m, 9H); 7.58-7. 61 (m, 2H); 7.73-7. 76 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Chelmical synthesis: Peptides were synthesized on a Rink amide resin, 0.45 mmol/g [Fmoc-Cys(Trityl)-Wang; Novabiochem, San Diego, Calif.] usinig N-(9-fluorenyl)methoxycarboxyl chemistry and standard side chain protection except on cysteine residues. Cysteine residues were protected in pairs with either S-trityl on the first and third cysteines or S-acetamidomethyl on the second and fourth cysteines. Amino acid derivatives were from Advanced Chemtech (Louisville, Ky.). The peptides were removed from the resin and precipitated, and a two-step oxidation protocol was used to selectively fold the peptides as described previously (Luo et al., 1999). Briefly, the first disulfide bridge was closed by dripping the peptide into an equal volume of 20 mM potassium feliicyanide and 0.1 M Tris, pH 7.5. The solution was allowed to react for 30 min, and the monocyclic peptide was purified by reverse-phase HPLC. Simultaneous removal of the S-acetamidomethyl groups and closure of the second disulfide bridge was carried out by iodine oxidation. The monocyclic peptide and HPLC eluent was dripped into an equal volume of iodine (10 mM) in H20/trifluoroacetic acid/acetonitrile (78:2:20 by volume) and allowed to react for 10 min. The reaction was terminated by the addition of ascorbic acid diluted 20-fold with 0.1percent trifluoroacetic acid and the bicyclic product purified by HPLC. Mass Spectrometry: Measurements were performed at the Salk Institute for Biological Studies (San Diego, Calif.) under the direction of Jean Rivier. Matrix-assisted laser desorption ionization time-of-flight mass spectrometry and liquid secondary ionization mass spectrometry were used. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Steps 3 through 6 were then repeated with the following order of amino acids:Fmoc-Cys(Acm)Fmoc-Ser(Bzl)Fmoc-Gly |
A394173 [159610-93-2]
(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-methoxypropanoic acid
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