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

ID: ALA4085837

PubChem CID: 11362429

Max Phase: Preclinical

Molecular Formula: C25H20ClN3O2

Molecular Weight: 429.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)Cc1ccc2c(C3=C(c4c[nH]c5ccccc45)C(=O)NC3=O)c(Cl)ccc2c1

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

Standard InChI Key:  VDBJPTBJJMQNOW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   22.3902  -18.4611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2074  -18.4611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4617  -17.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7988  -17.2023    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1400  -17.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6843  -19.1210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4309  -19.8979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0915  -20.3790    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.5014  -19.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7514  -19.8960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5450  -20.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0895  -19.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8349  -18.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0418  -18.5201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7431  -19.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9690  -18.8328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3463  -19.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4970  -20.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8952  -19.9100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2767  -20.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4291  -21.2424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1996  -21.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8180  -20.9735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6623  -20.1755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2393  -17.4330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3627  -17.4322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8203  -18.0293    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   22.3541  -22.3134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7363  -22.8484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8907  -23.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9641  -22.5809    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
 22 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4085837

   3-[2-chloro-6-[(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: 8.92

CX LogP: 3.99

CX LogD: 2.75

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.47

Np Likeness Score: -0.42

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