3-(2-chloro-7-((4-methylpiperazin-1-yl)methyl)naphthalen-1-yl)-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione

ID: ALA4068028

PubChem CID: 11547825

Max Phase: Preclinical

Molecular Formula: C29H27ClN4O2

Molecular Weight: 499.01

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCN(Cc2ccc3ccc(Cl)c(C4=C(c5cn(C)c6ccccc56)C(=O)NC4=O)c3c2)CC1

Standard InChI:  InChI=1S/C29H27ClN4O2/c1-32-11-13-34(14-12-32)16-18-7-8-19-9-10-23(30)25(21(19)15-18)27-26(28(35)31-29(27)36)22-17-33(2)24-6-4-3-5-20(22)24/h3-10,15,17H,11-14,16H2,1-2H3,(H,31,35,36)

Standard InChI Key:  BNAXHIOTDMDOLF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 36 41  0  0  0  0  0  0  0  0999 V2000
   14.0325   -2.1957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8497   -2.1957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1041   -1.4190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4411   -0.9369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7824   -1.4190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3266   -2.8556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0732   -3.6325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7338   -4.1136    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1438   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3938   -3.6305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1874   -3.7997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7319   -3.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4772   -2.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6842   -2.2546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3855   -2.8429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6114   -2.5674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9887   -3.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1393   -3.9081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5376   -3.6446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9190   -4.1771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0715   -4.9770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8420   -5.2456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4603   -4.7081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3047   -3.9101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8817   -1.1676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0051   -1.1668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4626   -1.7639    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.7348   -4.9308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2331   -4.9739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3893   -5.7760    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7702   -6.3076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9238   -7.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6955   -7.3765    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3141   -6.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1610   -6.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8487   -8.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  6  7  2  0
  7  8  1  0
  8 10  1  0
  9  6  1  0
  2  6  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  1 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 20  1  0
 19 15  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 19  2  0
  3 25  2  0
  5 26  2  0
 16 27  1  0
  8 28  1  0
 23 29  1  0
 29 30  1  0
 30 31  1  0
 30 35  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 33 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4068028

   3-[2-Chloro-7-[(4-methylpiperazin-1-yl)methyl]naphthalen-1-yl]-4-(1-methylindol-3-yl)pyrrole-2,5-dione

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: 499.01

Molecular Weight (Monoisotopic): 498.1823

AlogP: 4.30

#Rotatable Bonds: 4

Polar Surface Area: 57.58

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.87

CX Basic pKa: 7.95

CX LogP: 4.40

CX LogD: 3.74

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.43

Np Likeness Score: -0.75

References

1. van Eis MJ, Evenou J, Schuler W, Zenke G, Vangrevelinghe E, Wagner J, von Matt P..  (2017)  Indolyl-naphthyl-maleimides as potent and selective inhibitors of protein kinase C-α/β.,  27  (4): [PMID:28131714] [10.1016/j.bmcl.2017.01.038]

Source

Source(1):

• Scientific Literature