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Chemical Structure| 122889-11-6 Chemical Structure| 122889-11-6

Structure of Fmoc-D-Ser(Bzl)-OH
CAS No.: 122889-11-6

Chemical Structure| 122889-11-6

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Synonyms: N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-(phenylmethyl)-D-serine

4.5 *For Research Use Only !

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Product Details of [ 122889-11-6 ]

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

Safety of [ 122889-11-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 122889-11-6 ] Show Less

Physicochemical Properties

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
Ertl P. et al. 2000 J. Med. Chem.

84.86 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.74
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

4.03
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

4.04
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

2.82
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

3.98
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.52

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-4.74
Solubility 0.00765 mg/ml ; 0.0000183 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-5.52
Solubility 0.00127 mg/ml ; 0.00000305 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-7.5
Solubility 0.0000133 mg/ml ; 0.0000000318 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Poorly soluble

Pharmacokinetics

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)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

Yes
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

Yes
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

Yes
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

Yes
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.99 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.56

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<3.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

4.31

Application In Synthesis of [ 122889-11-6 ]

* 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.

  • Downstream synthetic route of [ 122889-11-6 ]

[ 122889-11-6 ] Synthesis Path-Downstream   1~39

  • 2
  • [ 5350-57-2 ]
  • [ 122889-11-6 ]
  • [ 98694-89-4 ]
  • 3
  • [ 122889-11-6 ]
  • [ 125827-94-3 ]
  • (S)-3-Benzyloxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid (2S,3R,4S,5S,6R)-5-benzyloxy-6-benzyloxymethyl-3-iodo-4-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl ester [ No CAS ]
  • (S)-3-Benzyloxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid (2R,3R,4S,5S,6R)-5-benzyloxy-6-benzyloxymethyl-3-iodo-4-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl ester [ No CAS ]
  • (S)-3-Benzyloxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid (2R,3S,4S,5S,6R)-5-benzyloxy-6-benzyloxymethyl-3-iodo-4-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl ester [ No CAS ]
  • 4
  • [ 122889-11-6 ]
  • [ 2748-02-9 ]
  • [ 118235-08-8 ]
  • 5
  • [ 122889-11-6 ]
  • [ 83345-52-2 ]
  • 6
  • [ 122889-11-6 ]
  • [ 157506-72-4 ]
  • 9
  • [ 29022-11-5 ]
  • [ 122889-11-6 ]
  • [ 35661-40-6 ]
  • [ 108-24-7 ]
  • [ 198561-07-8 ]
  • Ac-Ser(Bzl)-Asp-Phe-Gly-OH [ No CAS ]
  • 10
  • [ 122889-11-6 ]
  • [ 202868-77-7 ]
  • 11
  • [ 122889-11-6 ]
  • 3-(6-azidomethyl-2,2-dimethyl-tetrahydro-furo[3,4-<i>d</i>][1,3]dioxol-4-yloxy)-2-(9<i>H</i>-fluoren-9-ylmethoxycarbonylamino)-propionic acid <i>tert</i>-butyl ester [ No CAS ]
  • 12
  • [ 122889-11-6 ]
  • 3-(6-azidomethyl-2,2-dimethyl-tetrahydro-furo[3,4-<i>d</i>][1,3]dioxol-4-yloxy)-2-(9<i>H</i>-fluoren-9-ylmethoxycarbonylamino)-propionic acid <i>tert</i>-butyl ester [ No CAS ]
  • 13
  • [ 122889-11-6 ]
  • [ 110797-35-8 ]
  • 14
  • [ 122889-11-6 ]
  • [ 849063-79-2 ]
  • 15
  • [ 122889-11-6 ]
  • [ 849063-78-1 ]
  • 17
  • [ 122889-11-6 ]
  • [ 675882-23-2 ]
  • 18
  • [ 122889-11-6 ]
  • H-Glo[-Ser(Bzl)-Gly-OH]-OH*TFA [ No CAS ]
  • 19
  • [ 122889-11-6 ]
  • Cbz-His-OH [ No CAS ]
  • (S,Z)-(1-benzyloxymethyl-3-methoxyallyl)carbamic acid 9H-fluoren-9-yl methyl ester [ No CAS ]
  • 20
  • [ 122889-11-6 ]
  • Cbz-His-OH [ No CAS ]
  • (S,E)-(1-benzyloxymethyl-3-methoxyallyl)carbamic acid 9H-fluoren-9-yl methyl ester [ No CAS ]
  • 23
  • [ 122889-11-6 ]
  • [ 84000-14-6 ]
  • 24
  • [ 122889-11-6 ]
  • [ 84000-16-8 ]
  • 25
  • [ 122889-11-6 ]
  • [ 118235-08-8 ]
  • 26
  • [ 540-88-5 ]
  • [ 122889-11-6 ]
  • [ 305836-50-4 ]
YieldReaction ConditionsOperation 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).
  • 27
  • C34H28N2O7 [ No CAS ]
  • [ 29022-11-5 ]
  • [ 68858-20-8 ]
  • [ 35661-60-0 ]
  • [ 35661-39-3 ]
  • [ 122889-11-6 ]
  • [ 71989-31-6 ]
  • [ 71989-18-9 ]
  • [ 103213-32-7 ]
  • [ 86060-81-3 ]
  • [ 116611-64-4 ]
  • [ 223416-45-3 ]
YieldReaction ConditionsOperation 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.
YieldReaction ConditionsOperation in experiment
Steps 3 through 6 were then repeated with the following order of amino acids:Fmoc-Cys(Acm)Fmoc-Ser(Bzl)Fmoc-Gly
  • 29
  • [ 10065-72-2 ]
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  • [ 1013917-04-8 ]
  • 30
  • [ 2627-86-3 ]
  • [ 122889-11-6 ]
  • [ 877669-40-4 ]
  • 31
  • [ 3886-69-9 ]
  • [ 122889-11-6 ]
  • [ 877669-42-6 ]
  • 32
  • [ 122889-11-6 ]
  • [ 618-36-0 ]
  • [ 877669-39-1 ]
  • 33
  • C41H42ClN2O7Pol [ No CAS ]
  • [ 122889-11-6 ]
  • C66H63ClN3O11Pol [ No CAS ]
  • 34
  • C36H46ClO3Pol [ No CAS ]
  • [ 122889-11-6 ]
  • C61H67ClNO7Pol [ No CAS ]
  • C61H67ClNO7Pol [ No CAS ]
  • 35
  • C36H46ClO3Pol [ No CAS ]
  • [ 122889-11-6 ]
  • C61H67ClNO7Pol [ No CAS ]
  • C61H67ClNO7Pol [ No CAS ]
  • 36
  • C36H46ClO3Pol [ No CAS ]
  • [ 122889-11-6 ]
  • C61H67ClNO7Pol [ No CAS ]
  • C61H67ClNO7Pol [ No CAS ]
  • 37
  • C36H46ClO3Pol [ No CAS ]
  • [ 122889-11-6 ]
  • C61H67ClNO7Pol [ No CAS ]
  • C61H67ClNO7Pol [ No CAS ]
  • 39
  • C14H17N2O2Pol [ No CAS ]
  • [ 122889-11-6 ]
  • C39H38N3O6Pol [ No CAS ]
 

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Technical Information

Categories

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[ 122889-11-6 ]

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