3-[1-(3-Dimethylamino-propyl)-1H-indol-3-yl]-4-(1-methyl-1H-indol-3-yl)-pyrrole-2,5-dione

ID: ALA268769

PubChem CID: 5327726

Max Phase: Preclinical

Molecular Formula: C26H26N4O2

Molecular Weight: 426.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)CCCn1cc(C2=C(c3cn(C)c4ccccc34)C(=O)NC2=O)c2ccccc21

Standard InChI:  InChI=1S/C26H26N4O2/c1-28(2)13-8-14-30-16-20(18-10-5-7-12-22(18)30)24-23(25(31)27-26(24)32)19-15-29(3)21-11-6-4-9-17(19)21/h4-7,9-12,15-16H,8,13-14H2,1-3H3,(H,27,31,32)

Standard InChI Key:  WHOOZDLAJIKMBZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   16.1232  -14.9879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2925  -15.7978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6766  -16.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3424  -14.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7252  -15.2745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8884  -16.0845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1684  -16.4902    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5601  -15.9308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9042  -15.1794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0476  -15.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0464  -16.4466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7612  -16.8594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7594  -15.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4747  -15.6157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4795  -16.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2669  -16.6928    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2591  -15.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7444  -16.0197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5873  -14.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3981  -14.5112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5580  -13.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8461  -13.3111    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2462  -13.8649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3074  -13.3659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5286  -17.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9818  -18.0928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2435  -18.8752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6968  -19.4929    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9584  -20.2752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8884  -19.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0735  -17.3096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4372  -13.7033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0
 15 16  1  0
 16 18  1  0
 17 14  1  0
  6  7  1  0
  7  8  1  0
 17 18  2  0
  9 20  1  0
 19 17  1  0
 19 20  2  0
  8  9  2  0
  9  5  1  0
  4  1  1  0
  5  6  1  0
 10 11  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 19  1  0
 21 24  2  0
 11 12  1  0
 16 25  1  0
 12 15  2  0
 25 26  1  0
  2  3  1  0
 26 27  1  0
 14 13  2  0
 27 28  1  0
 13 10  1  0
 28 29  1  0
 14 15  1  0
 28 30  1  0
  3  6  2  0
  7 31  1  0
  1  2  2  0
 23 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA268769

   2-[1-(3-Dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleimide

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: 426.52

Molecular Weight (Monoisotopic): 426.2056

AlogP: 3.65

#Rotatable Bonds: 6

Polar Surface Area: 59.27

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.99

CX Basic pKa: 9.39

CX LogP: 2.80

CX LogD: 1.18

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.48

Np Likeness Score: -0.69

References

1. Davis PD, Elliott LH, Harris W, Hill CH, Hurst SA, Keech E, Kumar MK, Lawton G, Nixon JS, Wilkinson SE..  (1992)  Inhibitors of protein kinase C. 2. Substituted bisindolylmaleimides with improved potency and selectivity.,  35  (6): [PMID:1552513] [10.1021/jm00084a004]

2. McGovern SL, Shoichet BK..  (2003)  Kinase inhibitors: not just for kinases anymore.,  46  (8): [PMID:12672248] [10.1021/jm020427b]

3. Olla S, Manetti F, Crespan E, Maga G, Angelucci A, Schenone S, Bologna M, Botta M..  (2009)  Indolyl-pyrrolone as a new scaffold for Pim1 inhibitors.,  19  (5): [PMID:19179076] [10.1016/j.bmcl.2009.01.005]

Source

Source(1):

• Scientific Literature