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Chemical Structure| 5432-53-1 Chemical Structure| 5432-53-1

Structure of 5432-53-1

Chemical Structure| 5432-53-1

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Product Details of [ 5432-53-1 ]

CAS No. :5432-53-1
Formula : C12H15NO
M.W : 189.25
SMILES Code : CC(/C=C/C1=CC=C(N(C)C)C=C1)=O
MDL No. :MFCD00052839
InChI Key :IAMOQOMGCKCSEJ-SNAWJCMRSA-N
Pubchem ID :736580

Safety of [ 5432-53-1 ]

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

Computational Chemistry of [ 5432-53-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 6
Fraction Csp3 0.25
Num. rotatable bonds 3
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 60.55
TPSA ?

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

20.31 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.3
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

2.66
Log Po/w (WLOGP)?

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

2.25
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.

2.23
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

2.31
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.35

Water Solubility

Log S (ESOL):?

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

-2.81
Solubility 0.294 mg/ml ; 0.00155 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.

-2.74
Solubility 0.346 mg/ml ; 0.00183 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

-2.94
Solubility 0.219 mg/ml ; 0.00116 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

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

Yes
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.

-5.57 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

1.0
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.

1.0 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)

2.0

Application In Synthesis of [ 5432-53-1 ]

* 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.

  • Downstream synthetic route of [ 5432-53-1 ]

[ 5432-53-1 ] Synthesis Path-Downstream   1~35

  • 2
  • [ 5432-53-1 ]
  • [ 3119-93-5 ]
  • 3-ethyl-2-[4-(4-dimethylamino-phenyl)-2-methyl-buta-1,3-dienyl]-benzothiazolium; iodide [ No CAS ]
  • 3
  • [ 5432-53-1 ]
  • [ 30780-30-4 ]
YieldReaction ConditionsOperation in experiment
29.7% With palladium 10% on activated carbon; hydrogen; In methanol; under 1551.49 Torr; for 3.0h; General procedure: 4-Phenylbut-3-en-2-one (5 g) was dissolved in methanol (100 ml) and 10% Pd/C was added to it. The reaction mixture was shaken in a Parr shaker reactor under hydrogen pressure (30 psi) for 3 h. The reaction mixture was filtered over celite, washed with methanol (50 ml) and concentrated under reduced pressure. The crude product obtained was purified by column chromatography (Silica gel, 100-200 mesh, 9:1 hexane/ethyl acetate) to give the pure product.
  • 4
  • [ 5432-53-1 ]
  • [ 6673-14-9 ]
  • 5
  • [ 5432-53-1 ]
  • [ 3274-63-3 ]
  • 5-[3-(4-dimethylamino-phenyl)-1-methyl-allylidene]-2-methyl-4-phenyl-5<i>H</i>-pyrrole-3-carboxylic acid ethyl ester [ No CAS ]
  • 6
  • [ 5432-53-1 ]
  • [ 91-56-5 ]
  • [ 108135-89-3 ]
  • 7
  • [ 5432-53-1 ]
  • [ 141-97-9 ]
  • [ 861316-02-1 ]
  • 8
  • [ 5432-53-1 ]
  • [ 555-16-8 ]
  • [ 6597-45-1 ]
  • 11
  • [ 5432-53-1 ]
  • [ 90-02-8 ]
  • [ 97355-64-1 ]
  • 12
  • [ 5432-53-1 ]
  • [ 97-51-8 ]
  • 1-(4-dimethylamino-phenyl)-5-(2-hydroxy-5-nitro-phenyl)-penta-1,4-dien-3-one [ No CAS ]
  • 14
  • [ 64-17-5 ]
  • furan-2,3,5(4H)-trione pyridine (1:1) [ No CAS ]
  • [ 100-10-7 ]
  • [ 67-64-1 ]
  • [ 5432-53-1 ]
  • 15
  • [ 100-10-7 ]
  • [ 67-64-1 ]
  • [ 5432-53-1 ]
YieldReaction ConditionsOperation in experiment
67.73% With sodium hydroxide; In water; at 0 - 20℃; General procedure: A solution of substituted benzaldehydes (50 mmol) in acetone (50 ml) was cooled to 0C in an ice bath. To this a 10% aqueous NaOH solution was added dropwise and the reaction mixture was allowed to attain RT. It was then stirred at room temperature till the completion of the reaction. Acetone was removed under reduced pressure and the reaction was dissolved in ethyl acetate and washed with dilute HCl. The organic layer was separated wash twice with water, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography (Silica gel, 100-200 mesh, 9:1 hexane/ethyl acetate) to give the pure product.
  • 16
  • [ 5432-53-1 ]
  • [ 708-06-5 ]
  • 3-(4-dimethylamino-styryl)-benzo[<i>f</i>]chromenylium; perchlorate [ No CAS ]
  • 17
  • [ 5432-53-1 ]
  • [ 24777-76-2 ]
  • <i>N</i>'-[3-(4-dimethylamino-phenyl)-1-methyl-allylidene]-morpholine-4-carbohydrazonic acid amide [ No CAS ]
  • 18
  • [ 5432-53-1 ]
  • [ 20064-94-2 ]
  • <i>N</i>,<i>N</i>-dimethyl-4-[3-methyl-4-(6-methyl-benzothiazol-2-yl)-buta-1,3-dienyl]-aniline [ No CAS ]
  • 19
  • [ 98-01-1 ]
  • [ 5432-53-1 ]
  • [ 6673-14-9 ]
  • 20
  • [ 5432-53-1 ]
  • [ 151-50-8 ]
  • [ 82323-84-0 ]
  • 21
  • [ 5432-53-1 ]
  • [ 30780-30-4 ]
  • [ 120049-61-8 ]
  • [ 134747-44-7 ]
  • 22
  • [ 5432-53-1 ]
  • [ 57727-79-4 ]
  • Dimethyl-{4-[(E)-2-(3-quinolin-2-yl-benzo[f]quinolin-2-yl)-vinyl]-phenyl}-amine [ No CAS ]
  • 23
  • [ 100573-13-5 ]
  • [ 5432-53-1 ]
  • 24
  • [ 5432-53-1 ]
  • [ 105-53-3 ]
  • Sodium; 5-(4-dimethylamino-phenyl)-6-ethoxycarbonyl-3-oxo-cyclohex-1-enolate [ No CAS ]
  • 25
  • [ 5432-53-1 ]
  • [ 5305-00-0 ]
  • (E)-4-<4-(4-Dimethylaminophenyl)-3-buten-2-yliden>-2-phenylisoxazolidin-3,5-dion [ No CAS ]
  • (Z)-4-<4-(4-Dimethylaminophenyl)-3-buten-2-yliden>-2-phenylisoxazolidin-3,5-dion [ No CAS ]
  • 26
  • [ 934-32-7 ]
  • [ 5432-53-1 ]
  • Dimethyl-[4-(2-methyl-1,4-dihydro-benzo[4,5]imidazo[1,2-a]pyrimidin-4-yl)-phenyl]-amine [ No CAS ]
  • 27
  • [ 5432-53-1 ]
  • [ 2582-30-1 ]
  • C13H19N5 [ No CAS ]
  • 28
  • [ 5432-53-1 ]
  • [ 861296-59-5 ]
  • 29
  • [ 5432-53-1 ]
  • [ 55420-64-9 ]
  • 30
  • [ 5432-53-1 ]
  • [ 109-77-3 ]
  • 3-amino-2,4-dicyano-4'-dimethylamino-5-methylbiphenyl [ No CAS ]
  • 34
  • [ 5432-53-1 ]
  • aqueous-alcoholic NaOH-solution [ No CAS ]
  • [ 6673-14-9 ]
  • 35
  • [ 5432-53-1 ]
  • [ 141-97-9 ]
  • aqueous-alcoholic NaOH-solution [ No CAS ]
  • [ 861316-02-1 ]
 

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