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

ID: ALA4102228

PubChem CID: 11247414

Max Phase: Preclinical

Molecular Formula: C25H20ClN3O2

Molecular Weight: 429.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)Cc1ccc2ccc(Cl)c(C3=C(c4c[nH]c5ccccc45)C(=O)NC3=O)c2c1

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

Standard InChI Key:  HODOOWOVFQSXBB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   23.3601  -10.1117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6145   -9.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9515   -8.8529    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.2927   -9.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8370  -10.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5836  -11.5485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2442  -12.0296    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.6542  -10.7726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9041  -11.5466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6978  -11.7157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   21.5818  -12.8931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3523  -13.1616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9707  -12.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8150  -11.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7434  -12.8899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8996  -13.6920    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.3920   -9.0836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5154   -9.0829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9730   -9.6799    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   23.2831  -14.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6724  -13.9578    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
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 12 13  1  0
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 14  9  1  0
  1 15  1  0
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 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
 26 30  1  0
 26 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4102228

   3-[2-chloro-7-[(dimethylamino)methyl]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: 429.91

Molecular Weight (Monoisotopic): 429.1244

AlogP: 4.60

#Rotatable Bonds: 4

Polar Surface Area: 65.20

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.91

CX Basic pKa: 8.91

CX LogP: 3.99

CX LogD: 2.76

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.47

Np Likeness Score: -0.43

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