1-(1-Methyl-1H-indol-3-yl)-3-[2-(4-methyl-piperazin-1-yl)-phenyl]-propenone

ID: ALA1834563

PubChem CID: 56671788

Max Phase: Preclinical

Molecular Formula: C23H25N3O

Molecular Weight: 359.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCN(c2ccccc2/C=C/C(=O)c2cn(C)c3ccccc23)CC1

Standard InChI:  InChI=1S/C23H25N3O/c1-24-13-15-26(16-14-24)21-9-5-3-7-18(21)11-12-23(27)20-17-25(2)22-10-6-4-8-19(20)22/h3-12,17H,13-16H2,1-2H3/b12-11+

Standard InChI Key:  PDSODPRWKCNFBT-VAWYXSNFSA-N

Molfile:  

     RDKit          2D

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   -2.6479   -1.8687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8507   -2.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2844   -0.4863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4875   -0.6939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2655   -1.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4360   -1.5303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1452   -0.7524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7950   -0.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0193   -2.2183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7591    0.5886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0273    0.9696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4741    1.0001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6877    0.5580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4016    0.9715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1215    0.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8270    0.9929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8140    1.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0885    2.2183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3847    1.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1342   -0.2863    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4248   -0.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4353   -1.5289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8631   -1.5122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8542   -0.6852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1538   -1.9340    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1538   -2.7590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
 11 13  2  0
  3  6  2  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
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  7  8  1  0
 17 18  2  0
  8  9  2  0
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  9  5  1  0
 19 20  2  0
 20 15  1  0
 21 22  1  0
  4  1  1  0
  7 10  1  0
  5  6  1  0
  9 11  1  0
 11 12  1  0
 21 25  1  0
 22 23  1  0
 23 26  1  0
 26 24  1  0
 24 25  1  0
 16 21  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1834563

   (E)-1-(1-methylindol-3-yl)-3-[2-(4-methylpiperazin-1-yl)phenyl]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: 359.47

Molecular Weight (Monoisotopic): 359.1998

AlogP: 3.83

#Rotatable Bonds: 4

Polar Surface Area: 28.48

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.10

CX LogP: 4.17

CX LogD: 3.99

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.52

Np Likeness Score: -0.76

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]

Source

Source(1):

• Scientific Literature