2-(((4-(diethylamino)-2-methylphenyl)amino)methyl)isoindoline-1,3-dione

ID: ALA3781117

PubChem CID: 304956

Max Phase: Preclinical

Molecular Formula: C20H23N3O2

Molecular Weight: 337.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC)c1ccc(NCN2C(=O)c3ccccc3C2=O)c(C)c1

Standard InChI:  InChI=1S/C20H23N3O2/c1-4-22(5-2)15-10-11-18(14(3)12-15)21-13-23-19(24)16-8-6-7-9-17(16)20(23)25/h6-12,21H,4-5,13H2,1-3H3

Standard InChI Key:  GFZMGVOOUHJBBS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    1.7138   -1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0907   -2.3426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0825    2.3453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0872    0.0382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8208    1.3475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3215    1.3677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0567    2.6752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5566    2.6924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3214    1.4020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5863    0.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0864    0.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4449    3.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8222    1.4161    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5856    0.1239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7855    0.1351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5627    2.7215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7626    2.7314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  1  9  1  0
  4  9  2  0
  1 10  2  0
  3 11  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 14 19  2  0
 15 20  1  0
 22 23  1  0
 21 22  1  0
 24 25  1  0
 21 24  1  0
 17 21  1  0
 13 14  1  0
 12 13  1  0
  2 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3781117

   2-[[4-(Diethylamino)-2-methylanilino]methyl]isoindole-1,3-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: 337.42

Molecular Weight (Monoisotopic): 337.1790

AlogP: 3.51

#Rotatable Bonds: 6

Polar Surface Area: 52.65

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.53

CX LogP: 3.64

CX LogD: 3.27

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.82

Np Likeness Score: -1.48

References

1. Zhou W, Li S, Lu W, Yuan J, Xu Y, Li H, Huang J, Zhao Z.  (2016)  Isoindole-1,3-dione derivatives as RSK2 inhibitors: synthesis, molecular docking simulation and SAR analysis,  7  (2): [10.1039/C5MD00469A]

Source

Source(1):

• Scientific Literature