3-(4-((4-methylbenzyl)amino)-1-oxoisoindolin-2-yl)piperidine-2,6-dione

ID: ALA4095889

PubChem CID: 137655477

Max Phase: Preclinical

Molecular Formula: C21H21N3O3

Molecular Weight: 363.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(CNc2cccc3c2CN(C2CCC(=O)NC2=O)C3=O)cc1

Standard InChI:  InChI=1S/C21H21N3O3/c1-13-5-7-14(8-6-13)11-22-17-4-2-3-15-16(17)12-24(21(15)27)18-9-10-19(25)23-20(18)26/h2-8,18,22H,9-12H2,1H3,(H,23,25,26)

Standard InChI Key:  GKNIZGJYLWKLMB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   12.4526  -11.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4514  -11.8938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1662  -12.3067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1644  -10.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8798  -11.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8846  -11.8893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6721  -12.1400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1540  -11.4686    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6643  -10.8029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9782  -11.4624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3936  -12.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2150  -12.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6272  -11.4584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2117  -10.7445    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3840  -10.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1672  -13.1317    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4533  -13.5451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4544  -14.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9146  -10.0169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9681  -10.0333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4522  -11.4566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7411  -14.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7418  -15.6037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4573  -16.0161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1736  -15.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1694  -14.7753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4594  -16.8411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
 10 11  1  0
 10 15  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  8 10  1  0
  3 16  1  0
 16 17  1  0
 17 18  1  0
  9 19  2  0
 15 20  2  0
 13 21  2  0
 18 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 18  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4095889

   ---

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: 363.42

Molecular Weight (Monoisotopic): 363.1583

AlogP: 2.37

#Rotatable Bonds: 4

Polar Surface Area: 78.51

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.61

CX Basic pKa: 2.29

CX LogP: 1.83

CX LogD: 1.83

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.82

Np Likeness Score: -0.39

References

1. Hu S, Yuan L, Yan H, Li Z..  (2017)  Design, synthesis and biological evaluation of Lenalidomide derivatives as tumor angiogenesis inhibitor.,  27  (17): [PMID:28757066] [10.1016/j.bmcl.2017.07.046]

Source

Source(1):

• Scientific Literature