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

ID: ALA4083182

PubChem CID: 11639520

Max Phase: Preclinical

Molecular Formula: C24H19N3O2

Molecular Weight: 381.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1cc(C2=C(c3cccc4ccc(CN)cc34)C(=O)NC2=O)c2ccccc21

Standard InChI:  InChI=1S/C24H19N3O2/c1-27-13-19(16-6-2-3-8-20(16)27)22-21(23(28)26-24(22)29)17-7-4-5-15-10-9-14(12-25)11-18(15)17/h2-11,13H,12,25H2,1H3,(H,26,28,29)

Standard InChI Key:  IYPFXBNRYNDIDC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
    4.3996   -2.8808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2168   -2.8808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4712   -2.1041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8082   -1.6220    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1494   -2.1041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6937   -3.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4403   -4.3176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1009   -4.7987    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5109   -3.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7608   -4.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5545   -4.4848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0989   -3.8809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8443   -3.1053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0512   -2.9398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1018   -5.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7525   -3.5281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9785   -3.2525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3558   -3.7857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5064   -4.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9046   -4.3298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2861   -4.8622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4385   -5.6622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2090   -5.9307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8274   -5.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6717   -4.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6001   -5.6590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7563   -6.4611    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2487   -1.8527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3721   -1.8520    0.0000 O   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
  8 15  1  0
  1 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 21  1  0
 20 16  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 20  2  0
 24 26  1  0
 26 27  1  0
  3 28  2  0
  5 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4083182

   3-[7-(Aminomethyl)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: 381.44

Molecular Weight (Monoisotopic): 381.1477

AlogP: 3.36

#Rotatable Bonds: 3

Polar Surface Area: 77.12

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.84

CX Basic pKa: 9.10

CX LogP: 2.64

CX LogD: 1.34

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.53

Np Likeness Score: -0.21

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