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

ID: ALA4089665

PubChem CID: 68682755

Max Phase: Preclinical

Molecular Formula: C24H18ClN3O2

Molecular Weight: 415.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1cc(C2=C(c3c(Cl)ccc4ccc(CN)cc34)C(=O)NC2=O)c2ccccc21

Standard InChI:  InChI=1S/C24H18ClN3O2/c1-28-12-17(15-4-2-3-5-19(15)28)21-22(24(30)27-23(21)29)20-16-10-13(11-26)6-7-14(16)8-9-18(20)25/h2-10,12H,11,26H2,1H3,(H,27,29,30)

Standard InChI Key:  RWYIXXFPIXIFNJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   13.9129  -18.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7300  -18.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9844  -17.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3215  -17.1982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6627  -17.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2070  -19.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9536  -19.8938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6141  -20.3749    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0241  -19.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2741  -19.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0677  -20.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6122  -19.4571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3575  -18.6814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5645  -18.5159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2658  -19.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4917  -18.8287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8690  -19.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0197  -20.1694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4179  -19.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7993  -20.4384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9518  -21.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7223  -21.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3406  -20.9693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1850  -20.1714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1134  -21.2351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2696  -22.0373    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7620  -17.4288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8854  -17.4281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3429  -18.0251    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.6151  -21.1921    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
 23 25  1  0
 25 26  1  0
  3 27  2  0
  5 28  2  0
 16 29  1  0
  8 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4089665

   3-[7-(Aminomethyl)-2-chloronaphthalen-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: 415.88

Molecular Weight (Monoisotopic): 415.1088

AlogP: 4.01

#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: 9.95

CX Basic pKa: 9.12

CX LogP: 3.31

CX LogD: 1.95

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.50

Np Likeness Score: -0.35

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