3-(6-(aminomethyl)naphthalen-1-yl)-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione

ID: ALA4072709

PubChem CID: 11315034

Max Phase: Preclinical

Molecular Formula: C24H19N3O2

Molecular Weight: 381.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1cc(C2=C(c3cccc4cc(CN)ccc34)C(=O)NC2=O)c2ccccc21

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

Standard InChI Key:  BLYAGPCWZUKSNN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
    4.4285  -17.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2457  -17.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5000  -16.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8371  -15.9146    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1783  -16.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7226  -17.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4692  -18.6102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1298  -19.0913    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5397  -17.8343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7897  -18.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5833  -18.7774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1278  -18.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8732  -17.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0801  -17.2324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1307  -19.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7814  -17.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0073  -17.5451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3846  -18.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5353  -18.8858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9335  -18.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3150  -19.1548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4674  -19.9547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2379  -20.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8563  -19.6858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7006  -18.8878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2776  -16.1453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4010  -16.1445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3924  -21.0257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7746  -21.5607    0.0000 N   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
  3 26  2  0
  5 27  2  0
 23 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4072709

   3-[6-(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: 9.11

CX LogP: 2.64

CX LogD: 1.33

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.53

Np Likeness Score: -0.22

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