1-(2-(((4-methoxyphenyl)amino)methyl)-1,3-dioxoisoindolin-5-yl)-3-phenylurea

ID: ALA3780618

PubChem CID: 127030459

Max Phase: Preclinical

Molecular Formula: C23H20N4O4

Molecular Weight: 416.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(NCN2C(=O)c3ccc(NC(=O)Nc4ccccc4)cc3C2=O)cc1

Standard InChI:  InChI=1S/C23H20N4O4/c1-31-18-10-7-15(8-11-18)24-14-27-21(28)19-12-9-17(13-20(19)22(27)29)26-23(30)25-16-5-3-2-4-6-16/h2-13,24H,14H2,1H3,(H2,25,26,30)

Standard InChI Key:  VIIJGMMTRBMJDR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   -3.6217    1.4865    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9153    0.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9050   -0.4745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2216    1.4644    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5151    0.7033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8219    1.4399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1132    0.6766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0978   -0.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7911   -1.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4999   -0.7967    0.0000 C   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
    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
    2.0825    2.3453    0.0000 O   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
    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
   10.8222    1.4161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4326    0.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  5 10  2  0
  4  5  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 11 19  1  0
 14 19  2  0
 13 20  2  0
 11 21  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 24 29  2  0
 30 31  1  0
 27 30  1  0
 23 24  1  0
 22 23  1  0
 12 22  1  0
  1 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3780618

   ---

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: 416.44

Molecular Weight (Monoisotopic): 416.1485

AlogP: 4.00

#Rotatable Bonds: 6

Polar Surface Area: 99.77

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.15

CX Basic pKa: 3.84

CX LogP: 3.29

CX LogD: 3.29

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.53

Np Likeness Score: -1.22

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