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Chemical Structure| 22479-95-4 Chemical Structure| 22479-95-4

Structure of 22479-95-4

Chemical Structure| 22479-95-4

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Product Details of [ 22479-95-4 ]

CAS No. :22479-95-4
Formula : C10H10O5
M.W : 210.18
SMILES Code : O=C(OC)C1=CC=C(O)C=C1C(OC)=O
MDL No. :MFCD00060092
InChI Key :JJXVDRYFBGDXOU-UHFFFAOYSA-N
Pubchem ID :89726

Safety of [ 22479-95-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335-H412
Precautionary Statements:P261-P273-P305+P351+P338

Computational Chemistry of [ 22479-95-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 15
Num. arom. heavy atoms 6
Fraction Csp3 0.2
Num. rotatable bonds 4
Num. H-bond acceptors 5.0
Num. H-bond donors 1.0
Molar Refractivity 51.02
TPSA ?

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

72.83 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.21
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

1.24
Log Po/w (WLOGP)?

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

0.97
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.

1.26
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

1.16
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.17

Water Solubility

Log S (ESOL):?

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

-1.96
Solubility 2.32 mg/ml ; 0.0111 mol/l
Class?

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

Very soluble
Log S (Ali)?

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

-2.37
Solubility 0.902 mg/ml ; 0.00429 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

-1.98
Solubility 2.19 mg/ml ; 0.0104 mol/l
Class?

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

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

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.

-6.7 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

1.0 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<1.0
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)

1.81

Application In Synthesis of [ 22479-95-4 ]

* 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.

  • Downstream synthetic route of [ 22479-95-4 ]

[ 22479-95-4 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 19064-24-5 ]
  • [ 22479-95-4 ]
  • [ 640296-13-5 ]
  • 3
  • [ 22479-95-4 ]
  • [ 74-88-4 ]
  • [ 1885-13-8 ]
  • 4
  • [ 57641-66-4 ]
  • [ 22479-95-4 ]
  • 1,2-dimethyl 4-[2-(2-hydroxyethoxy)ethoxy]phthalate [ No CAS ]
YieldReaction ConditionsOperation in experiment
2.22 g With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 1h;Inert atmosphere; To a stirred mixture of 1, 2-dimethyl 4-hydroxyphthalate (2 g, 9.52 mmol, 1.0 equiv) and K2CO3 (2.64 g, 19.1 mmol, 2.0 equiv) in DML (30 ml), was added 2-(2- bromoethoxy)ethanol (5 g, 29.6 mmol, 3.1 equiv) under nitrogen atmosphere. The reaction mixture was stirred for 1 hr at 70 C in an oil bath, and then cooled to room temperature. The reaction was quenched by the addition of water (100 mL). The resulting mixture was extracted with EtOAc (3 x 150 mL). The combined organic layers were washed with brine (4 x lOOml), dried over anhydrous Na2S04. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluting with EtOAc/ petroleum ether (0:1 to 3:2) to afford 1, 2-dimethyl 4-[2-(2-hydroxyethoxy)ethoxy]phthalate (2.22 g) as a light yellow oil.
  • 5
  • [ 34270-90-1 ]
  • [ 22479-95-4 ]
  • C24H26O11 [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With caesium carbonate; In acetonitrile; at 80℃; for 12h; General procedure: Step (1): Carry out substitution reaction using dimethyl 4-hydroxyphthalate as raw material;Specifically: put dimethyl 4-hydroxyphthalate and dihalo compound in anhydrous acetonitrile,Add an appropriate amount of cesium carbonate solid and stir at 80 C for 12 hours.The solid was removed by filtration, the filtrate was spin-dried, and purified by silica gel chromatography using petroleum ether / ethyl acetate or dichloromethane / methanol.
  • 6
  • [ 34270-90-1 ]
  • [ 22479-95-4 ]
  • C14H17IO6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; In acetonitrile; at 80℃; for 12h; General procedure: Step (1): Carry out substitution reaction using dimethyl 4-hydroxyphthalate as raw material;Specifically: put dimethyl 4-hydroxyphthalate and dihalo compound in anhydrous acetonitrile,Add an appropriate amount of cesium carbonate solid and stir at 80 C for 12 hours.The solid was removed by filtration, the filtrate was spin-dried, and purified by silica gel chromatography using petroleum ether / ethyl acetate or dichloromethane / methanol.
 

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