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

ID: ALA4061321

PubChem CID: 11624816

Max Phase: Preclinical

Molecular Formula: C23H17N3O2

Molecular Weight: 367.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCc1ccc2cccc(C3=C(c4c[nH]c5ccccc45)C(=O)NC3=O)c2c1

Standard InChI:  InChI=1S/C23H17N3O2/c24-11-13-8-9-14-4-3-6-16(17(14)10-13)20-21(23(28)26-22(20)27)18-12-25-19-7-2-1-5-15(18)19/h1-10,12,25H,11,24H2,(H,26,27,28)

Standard InChI Key:  BPRHUHLTGPELTP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
    4.5152  -10.3057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3323  -10.3057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5867   -9.5290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9238   -9.0469    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2650   -9.5290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8093  -10.9656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5559  -11.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2164  -12.2236    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6264  -10.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8764  -11.7406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6700  -11.9097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2145  -11.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9598  -10.5301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1668  -10.3647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8681  -10.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0940  -10.6774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4713  -11.2106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6220  -12.0181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0202  -11.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4016  -12.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5541  -13.0870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3246  -13.3556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9429  -12.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7873  -12.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7157  -13.0839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8719  -13.8860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3643   -9.2776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4877   -9.2768    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
  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
 23 25  1  0
 25 26  1  0
  3 27  2  0
  5 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4061321

   3-[7-(aminomethyl)naphthalen-1-yl]-4-(1H-indol-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: 367.41

Molecular Weight (Monoisotopic): 367.1321

AlogP: 3.35

#Rotatable Bonds: 3

Polar Surface Area: 87.98

Molecular Species: BASE

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.84

CX Basic pKa: 9.10

CX LogP: 2.42

CX LogD: 1.12

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.49

Np Likeness Score: 0.07

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