1,3-Bis-(1-methyl-1H-indol-3-yl)-propenone

ID: ALA1834570

PubChem CID: 56678496

Max Phase: Preclinical

Molecular Formula: C21H18N2O

Molecular Weight: 314.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1cc(/C=C/C(=O)c2cn(C)c3ccccc23)c2ccccc21

Standard InChI:  InChI=1S/C21H18N2O/c1-22-13-15(16-7-3-5-9-19(16)22)11-12-21(24)18-14-23(2)20-10-6-4-8-17(18)20/h3-14H,1-2H3/b12-11+

Standard InChI Key:  YAKSLYJQYXCGCH-VAWYXSNFSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    0.9957    0.9970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2797    0.5873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4332    1.0024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1171   -0.3098    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3017   -0.1838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1697    0.6305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9033    1.0078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1139    1.8054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9100    2.0219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4955    1.4408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2849    0.6431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4889    0.4266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4943   -1.0436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0133    0.2996    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4636    0.9147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7087    0.5819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7918   -0.2389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2376   -0.8499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4896   -1.6355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2959   -1.8100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8502   -1.1989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5982   -0.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8341    0.3827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4302    1.8274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  4 12  1  0
  7 12  2  0
  4 13  1  0
  3  6  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 14 22  1  0
 17 22  2  0
 14 23  1  0
  1 16  1  0
  3 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1834570

   (E)-1,3-bis(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: 314.39

Molecular Weight (Monoisotopic): 314.1419

AlogP: 4.57

#Rotatable Bonds: 3

Polar Surface Area: 26.93

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.54

CX LogD: 4.54

Aromatic Rings: 4

Heavy Atoms: 24

QED Weighted: 0.40

Np Likeness Score: -0.45

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