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

ID: ALA1834562

PubChem CID: 56657918

Max Phase: Preclinical

Molecular Formula: C23H25N3O

Molecular Weight: 359.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCN(c2ccc(/C=C/C(=O)c3cn(C)c4ccccc34)cc2)CC1

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

Standard InChI Key:  JPKIGFYTIQXJOX-FMIVXFBMSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   -1.9715   -9.4378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9726  -10.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2581  -10.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2599   -9.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5448   -9.4342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5399  -10.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2516  -10.5170    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7360   -9.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2437   -9.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5110  -11.2999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2910   -8.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0275   -7.9780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3985   -7.8968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7171   -8.4303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4536   -8.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1414   -8.5129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8773   -8.1426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9247   -7.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2302   -6.8659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4970   -7.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6578   -6.9474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3477   -7.4010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0814   -7.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4416   -5.7553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7016   -6.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1316   -6.2089    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8461   -5.7964    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
 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
 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
 18 21  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1834562

   (E)-1-(1-methylindol-3-yl)-3-[4-(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: 7.90

CX LogP: 4.17

CX LogD: 3.55

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.52

Np Likeness Score: -0.81

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