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Chemical Structure| 1082750-59-1 Chemical Structure| 1082750-59-1

Structure of 1082750-59-1

Chemical Structure| 1082750-59-1

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Product Details of [ 1082750-59-1 ]

CAS No. :1082750-59-1
Formula : C17H19NO4
M.W : 301.34
SMILES Code : O=C(O)[C@@H](NC(OC(C)(C)C)=O)C1=CC=C2C=CC=CC2=C1
MDL No. :MFCD07371920
InChI Key :MQCLXWDVGKUKHB-AWEZNQCLSA-N
Pubchem ID :51441081

Safety of [ 1082750-59-1 ]

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

Computational Chemistry of [ 1082750-59-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 22
Num. arom. heavy atoms 10
Fraction Csp3 0.29
Num. rotatable bonds 6
Num. H-bond acceptors 4.0
Num. H-bond donors 2.0
Molar Refractivity 84.04
TPSA ?

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

75.63 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.63
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

3.47
Log Po/w (WLOGP)?

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

3.17
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.

2.51
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

2.38
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.83

Water Solubility

Log S (ESOL):?

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

-3.83
Solubility 0.0441 mg/ml ; 0.000146 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.

-4.74
Solubility 0.00548 mg/ml ; 0.0000182 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

-4.43
Solubility 0.0111 mg/ml ; 0.0000367 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.

-5.67 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<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)

2.76

Application In Synthesis of [ 1082750-59-1 ]

* 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.

  • Upstream synthesis route of [ 1082750-59-1 ]

[ 1082750-59-1 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 1393112-52-1 ]
  • [ 1082750-59-1 ]
YieldReaction ConditionsOperation in experiment
91.5% With Tri-n-octylamine; sodium hydroxide; subtilisin In tert-butyl methyl ether; water at 37℃; for 216 h; Resolution of racemate; Enzymatic reaction General procedure: The DKR of 2a and 4a was carried out in a biphasic system. The reaction was carried out in an automatic titrator. To a solution of d,l-N-Boc-AA-SEt (6.5 mmol) in 50 mL of MTBE, water (100 mL) and trioctylamine (3.25 mmol) were added. The pH was adjusted to 8 with NaOH (0.5 M) and 500 U of subtilisin was added. The reaction was kept at pH 8 by the automatic addition of NaOH (0.5 M), at 37 °C with vigorous mechanical stirring. After 2 days, the consumption of NaOH 0.5 M reached 100percent of the theoretical. The water phase was separated from the organic layer and again extracted (at pH 8) with 30 mL of diethyl ether. The aqueous phase was brought to pH 3 by the dropwise addition of 6 M HCl. Next, 30 mL of ethyl acetate was added, and the resulting mixture was suction-filtered through a Celite bed. The organic phase was separated, and the aqueous layer was extracted twice with further 30 mL of ethyl acetate. The organic fractions were combined, dried, and evaporation of the solvent gave a quantitative amount of l-N-Boc-AA-OH. Enantiomeric excess analyzed by chiral HPLC was >99percent. l-N-Boc-AA-OH was deprotected with dioxane saturated with HCl at 60 °C to give of l-AA-OH*HCl as a white solid.
References: [1] Tetrahedron Asymmetry, 2012, vol. 23, # 13, p. 938 - 944.
  • 2
  • [ 1393112-56-5 ]
  • [ 1082750-59-1 ]
References: [1] Tetrahedron Asymmetry, 2012, vol. 23, # 13, p. 938 - 944.
  • 3
  • [ 33741-79-6 ]
  • [ 1082750-59-1 ]
References: [1] Tetrahedron Asymmetry, 2012, vol. 23, # 13, p. 938 - 944.
 

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