3-(2,4-Dimethoxy-phenyl)-1-(1-methyl-1H-indol-3-yl)-propenone

ID: ALA1834564

PubChem CID: 56675195

Max Phase: Preclinical

Molecular Formula: C20H19NO3

Molecular Weight: 321.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C/C(=O)c2cn(C)c3ccccc23)c(OC)c1

Standard InChI:  InChI=1S/C20H19NO3/c1-21-13-17(16-6-4-5-7-18(16)21)19(22)11-9-14-8-10-15(23-2)12-20(14)24-3/h4-13H,1-3H3/b11-9+

Standard InChI Key:  WLEGJNUYSIGWDD-PKNBQFBNSA-N

Molfile:  

     RDKit          2D

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    5.3545  -15.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5679  -16.7543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3665  -16.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9307  -15.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7288  -15.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9481  -16.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7788  -16.4171    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0693  -15.6395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4187  -15.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2350  -17.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4565  -14.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1852  -13.9201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7407  -13.8905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9008  -14.3305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6151  -13.9171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3342  -14.3517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0354  -13.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0240  -13.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3008  -12.6755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5978  -13.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8764  -12.7012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1712  -13.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7279  -12.6528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7136  -11.8289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 14  2  0
  1  2  2  0
 14 15  1  0
  5  4  2  0
 15 16  2  0
  6  7  1  0
 16 17  1  0
  7  8  1  0
 17 18  2  0
  8  9  2  0
 18 19  1  0
  9  5  1  0
 19 20  2  0
 20 15  1  0
  4  1  1  0
  7 10  1  0
  5  6  1  0
  9 11  1  0
 11 12  1  0
  2  3  1  0
 21 22  1  0
 20 21  1  0
 11 13  2  0
  3  6  2  0
 23 24  1  0
 18 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1834564

   (E)-3-(2,4-dimethoxyphenyl)-1-(1-methylindol-3-yl)prop-2-en-1-one

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 321.38

Molecular Weight (Monoisotopic): 321.1365

AlogP: 4.09

#Rotatable Bonds: 5

Polar Surface Area: 40.46

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.90

CX LogD: 3.90

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.52

Np Likeness Score: -0.40

References

1. Martel-Frachet V, Kadri M, Boumendjel A, Ronot X..  (2011)  Structural requirement of arylindolylpropenones as anti-bladder carcinoma cells agents.,  19  (20): [PMID:21908193] [10.1016/j.bmc.2011.08.015]

2. Valdameri G, Gauthier C, Terreux R, Kachadourian R, Day BJ, Winnischofer SM, Rocha ME, Frachet V, Ronot X, Di Pietro A, Boumendjel A..  (2012)  Investigation of chalcones as selective inhibitors of the breast cancer resistance protein: critical role of methoxylation in both inhibition potency and cytotoxicity.,  55  (7): [PMID:22449016] [10.1021/jm2016528]

Source

Source(1):

• Scientific Literature