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

ID: ALA4072879

PubChem CID: 11604381

Max Phase: Preclinical

Molecular Formula: C25H20ClN3O2

Molecular Weight: 429.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNCc1ccc2ccc(Cl)c(C3=C(c4cn(C)c5ccccc45)C(=O)NC3=O)c2c1

Standard InChI:  InChI=1S/C25H20ClN3O2/c1-27-12-14-7-8-15-9-10-19(26)21(17(15)11-14)23-22(24(30)28-25(23)31)18-13-29(2)20-6-4-3-5-16(18)20/h3-11,13,27H,12H2,1-2H3,(H,28,30,31)

Standard InChI Key:  ZMHXVAQNZDUNOG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   31.2059  -18.6840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0231  -18.6840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2775  -17.9073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6145  -17.4252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.9558  -17.9073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5000  -19.3439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2466  -20.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9072  -20.6019    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.3172  -19.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5672  -20.1188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3608  -20.2880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9053  -19.6841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6506  -18.9084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8576  -18.7429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5589  -19.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7848  -19.0557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1621  -19.5889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3127  -20.3964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7110  -20.1329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0924  -20.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2449  -21.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0154  -21.7338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6337  -21.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4781  -20.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0550  -17.6558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1785  -17.6551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.6360  -18.2521    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   32.9082  -21.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4065  -21.4621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5627  -22.2643    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.3354  -22.5301    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
M  END

Alternative Forms

1. Parent:

   

   ALA4072879

   3-[2-Chloro-7-(methylaminomethyl)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: 429.91

Molecular Weight (Monoisotopic): 429.1244

AlogP: 4.27

#Rotatable Bonds: 4

Polar Surface Area: 63.13

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.00

CX Basic pKa: 9.31

CX LogP: 3.70

CX LogD: 2.15

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.48

Np Likeness Score: -0.32

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