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Chemical Structure| 42406-77-9 Chemical Structure| 42406-77-9

Structure of H-Tyr-OBzl
CAS No.: 42406-77-9

Chemical Structure| 42406-77-9

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Product Details of [ 42406-77-9 ]

CAS No. :42406-77-9
Formula : C16H17NO3
M.W : 271.31
SMILES Code : [H][C@](N)(CC1=CC=C(O)C=C1)C(=O)OCC1=CC=CC=C1
MDL No. :MFCD00191034
InChI Key :BVCTWRNVKLXEQC-HNNXBMFYSA-N
Pubchem ID :104541

Safety of [ 42406-77-9 ]

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

Computational Chemistry of [ 42406-77-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 20
Num. arom. heavy atoms 12
Fraction Csp3 0.19
Num. rotatable bonds 6
Num. H-bond acceptors 4.0
Num. H-bond donors 2.0
Molar Refractivity 76.33
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

72.55 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.76
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

1.86
Log Po/w (WLOGP)?

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

1.85
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.

2.19
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

2.51
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.03

Water Solubility

Log S (ESOL):?

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

-2.74
Solubility 0.492 mg/ml ; 0.00181 mol/l
Class?

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

Soluble
Log S (Ali)?

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

-3.0
Solubility 0.268 mg/ml ; 0.000989 mol/l
Class?

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

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

-4.53
Solubility 0.00804 mg/ml ; 0.0000296 mol/l
Class?

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

Moderately 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

Yes
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

No
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

No
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

No
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

No
Log Kp (skin permeation)?

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

-6.63 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.

0.55

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<0.0
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)

2.44

Application In Synthesis of [ 42406-77-9 ]

* 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 [ 42406-77-9 ]

[ 42406-77-9 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 66065-85-8 ]
  • [ 42406-77-9 ]
  • [ 82911-82-8 ]
  • 2
  • [ 6624-49-3 ]
  • [ 42406-77-9 ]
  • [ 1184612-44-9 ]
YieldReaction ConditionsOperation in experiment
56% With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 0 - 20℃; for 14h;Inert atmosphere; General procedure: At 0 °C and with stirring to the solution of 865 mg (5.0 mmol) of <strong>[6624-49-3]isoquinoline-3-carboxylic acid</strong> in 10 ml of anhydrous THF 675 mg (5.0 mmol) of HOBt was added to form reaction mixture A. The solution of 5.5 mmol of l-amino acid benzylester in 5 ml of anhydrous THF was adjusted pH 9 with triethylamine and stirred for 30 min to form mixture B. At 0 °C the mixtures A and B were mixed and then 1339 mg (6.5 mmol) of DCC was added. The reaction mixture was stirred at 0 °C for 2 h, at room temperature for12 h and TLC (ethyl acetate/petroleum ether, 1:2) indicated the complete disappearance of <strong>[6624-49-3]isoquinoline-3-carboxylic acid</strong>. The formed precipitates of DCU were removed by filtration and the filtrate was evaporated under vacumm. The residue was dissolved in 50 ml of ethyl acetate and the formed solution was washed successively with saturated aqueous solution of NaHCO3 (30 ml .x. 3), 5percent aqueous solution of KHSO4 (30 ml .x. 3) and saturated aqueous solution of NaCl (30 ml .x. 3) and dried over anhydrous Na2SO4. After filtration the filtrate was evaporated under vacumm and the residure was purified on silica gel chromatography (CHCl3:MeOH, 20:1) to give the title compounds.
  • 3
  • [ 42406-77-9 ]
  • [ 13122-90-2 ]
  • C39H43N3O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: A flask was charged with 3-(N-phthalimidoadamantane)-1-carboxylic acid 6 (175 mg, 0.54 mmol), HBTU (224 mg, 0.59 mmol), HOBT (80 mg, 0.59 mmol), triethylamine (TEA; 157 lL, 1.13 mmol) and CH2Cl2 (dried over molecular sieves 4A). After stirring for 10 min at rt under inert N2-atmosphere, L-tyrosine benzyl ester (228 mg, 0.59 mmol) was added and the reaction was stirred for 3 days. When the reaction was completed, brine (30 mL) was added to the reaction mixture. The product was extracted with ethyl acetate (3 x 20 mL), and the extracts were washed with HCl (1 M, 15 mL), H2O (15 mL), saturated aqueous NaHCO3 (15 mL) and H2O (15 mL). The organic extracts were dried over anhydrous Na2SO4 and filtered, and the solvent was removed on a rotary evaporator, furnishing the product (270 mg, 87 %) which was purified by column chromatography on silica gel using CH2Cl2/MeOH (0-10 %) as eluent.
 

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