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Chemical Structure| 6322-83-4 Chemical Structure| 6322-83-4
Chemical Structure| 6322-83-4

2-(4-Benzoylphenoxy)acetic acid

CAS No.: 6322-83-4

4.5 *For Research Use Only !

Cat. No.: A173830 Purity: 97%

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Product Details of [ 6322-83-4 ]

CAS No. :6322-83-4
Formula : C15H12O4
M.W : 256.25
SMILES Code : O=C(O)COC1=CC=C(C(C2=CC=CC=C2)=O)C=C1
MDL No. :MFCD02725448
InChI Key :FQPOVZIKEBLFNG-UHFFFAOYSA-N
Pubchem ID :80609

Safety of [ 6322-83-4 ]

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

Calculated chemistry of [ 6322-83-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 19
Num. arom. heavy atoms 12
Fraction Csp3 0.07
Num. rotatable bonds 5
Num. H-bond acceptors 4.0
Num. H-bond donors 1.0
Molar Refractivity 69.39
TPSA ?

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

63.6 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.89
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

2.68
Log Po/w (WLOGP)?

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

2.38
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.

1.86
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

2.69
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.3

Water Solubility

Log S (ESOL):?

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

-3.25
Solubility 0.143 mg/ml ; 0.000556 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.

-3.67
Solubility 0.0551 mg/ml ; 0.000215 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

-4.39
Solubility 0.0105 mg/ml ; 0.0000411 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.

-5.96 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)

1.85

Application In Synthesis of [ 6322-83-4 ]

* 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 [ 6322-83-4 ]
  • Downstream synthetic route of [ 6322-83-4 ]

[ 6322-83-4 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 51848-56-7 ]
  • [ 6322-83-4 ]
YieldReaction ConditionsOperation in experiment
74%
Stage #1: With sodium hydroxide In ethanol at 20℃;
Stage #2: With hydrogenchloride In water at 0℃;
General procedure: A solution of NaOH 1N (3.9 mmol) was added to esters 7-16(3.0 mmol) in EtOH (20 mL), and the mixture was stirred at r.t. for 10-15 h. The solvent was removed under reducedpressure and the residue was poured into water (20 mL) andacidified with conc HCl at 0 °C. The aqueous layer was extractedwith dichloromethane (3 20 mL) and then the organiclayer was dried over Na2SO4 and concentrated underreduced pressure. The residue was purified by crystallizationwith cyclohexane or chloroform affording desired acids 17-26 with good yields.
References: [1] Medicinal Chemistry, 2014, vol. 10, # 1, p. 59 - 65.
[2] Anales de la Real Sociedad Espanola de Fisica y Quimica, vol. 24, p. 88[3] Chemisches Zentralblatt, 1926, vol. 97, # II, p. 21.
[4] Tetrahedron Letters, 2004, vol. 45, # 10, p. 2239 - 2241.
[5] Journal of Peptide Science, 2010, vol. 16, # 10, p. 551 - 557.
  • 2
  • [ 57682-09-4 ]
  • [ 6322-83-4 ]
YieldReaction ConditionsOperation in experiment
95% With water; lithium hydroxide In tetrahydrofuran; methanolHeating General procedure: To a solution of 5a-i (1.0 eq.) in a mixture of equal amounts of THF and methanol (0.5 M solution) was added an aqueous 1 M solution of LiOH (5.0 eq.). After 1 hour at 100 °C th esaponification of the esters 6a-q was completed shown by TLC (EtOAc/Pet. ether 1/3). While the mixture was cooled on ice, the pH was adjusted to pH = 1 using a 2 M HCl solution (aq.). The resulting precipitate was collected by filtration, washed with water, Pet. ether and co-evaporated with acetone to dryness. 1.7.1. 2-(4-Benzoylphenoxy)acetic acid (6a).[21] White solids 1.37 g, yield = 95percent. 1H NMR (400 MHz, CDCl3 + drop of DMSO): δ 9.50 (s br, 1H), 7.82 (d, J = 8.4 Hz, 2H), 7.75 (d, J = 7.6 Hz, 2H), 7.58 (t, J = 7.6 Hz, 1H), 7.47 (t, J = 7.6 Hz, 2H), 7.00 (d, J = 8.8 Hz, 2H), 4.69 (s, 2H) ppm.
References: [1] Journal of Mass Spectrometry, 2015, vol. 50, # 2, p. 407 - 417.
[2] European Journal of Medicinal Chemistry, 2015, vol. 106, p. 50 - 59.
[3] Patent: US2016/214967, 2016, A1, . Location in patent: Paragraph 0336; 0337.
  • 3
  • [ 1137-42-4 ]
  • [ 6322-83-4 ]
References: [1] Tetrahedron Letters, 2004, vol. 45, # 10, p. 2239 - 2241.
[2] Anales de la Real Sociedad Espanola de Fisica y Quimica, vol. 24, p. 88[3] Chemisches Zentralblatt, 1926, vol. 97, # II, p. 21.
[4] Medicinal Chemistry, 2014, vol. 10, # 1, p. 59 - 65.
[5] Journal of Mass Spectrometry, 2015, vol. 50, # 2, p. 407 - 417.
[6] European Journal of Medicinal Chemistry, 2015, vol. 106, p. 50 - 59.
  • 4
  • [ 2555-49-9 ]
  • [ 6322-83-4 ]
References: [1] Journal of Peptide Science, 2010, vol. 16, # 10, p. 551 - 557.
  • 5
  • [ 122-59-8 ]
  • [ 6322-83-4 ]
References: [1] Journal of Peptide Science, 2010, vol. 16, # 10, p. 551 - 557.
  • 6
  • [ 578-57-4 ]
  • [ 6322-83-4 ]
References: [1] European Journal of Medicinal Chemistry, 2015, vol. 106, p. 50 - 59.
  • 7
  • [ 98-88-4 ]
  • [ 6322-83-4 ]
References: [1] European Journal of Medicinal Chemistry, 2015, vol. 106, p. 50 - 59.
  • 8
  • [ 116413-49-1 ]
  • [ 6322-83-4 ]
References: [1] European Journal of Medicinal Chemistry, 2015, vol. 106, p. 50 - 59.
 

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