N-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)-4-methylbenzenesulfonamide

ID: ALA4088165

PubChem CID: 137642073

Max Phase: Preclinical

Molecular Formula: C20H19N3O5S

Molecular Weight: 413.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(S(=O)(=O)Nc2cccc3c2CN(C2CCC(=O)NC2=O)C3=O)cc1

Standard InChI:  InChI=1S/C20H19N3O5S/c1-12-5-7-13(8-6-12)29(27,28)22-16-4-2-3-14-15(16)11-23(20(14)26)17-9-10-18(24)21-19(17)25/h2-8,17,22H,9-11H2,1H3,(H,21,24,25)

Standard InChI Key:  INSBIAPVHBCNHS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   29.5035  -13.6314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.3282  -13.6355    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   29.9195  -12.9194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.3309  -11.1616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3297  -11.9887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0442  -12.4013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0424  -10.7491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7574  -11.1580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7623  -11.9840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5494  -12.2348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0311  -11.5636    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.5416  -10.8982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8550  -11.5575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2702  -12.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0912  -12.2681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5032  -11.5533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0879  -10.8398    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.2606  -10.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0452  -13.2259    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.3327  -14.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7919  -10.1124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.8449  -10.1289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.3279  -11.5516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.6197  -14.8730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6204  -15.6969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3356  -16.1092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0516  -15.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0473  -14.8690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3378  -16.9338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  8  1  0
 13 14  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 11 13  1  0
  6 19  1  0
 19  2  1  0
  2 20  1  0
 12 21  2  0
 18 22  2  0
 16 23  2  0
 20 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 20  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4088165

   ---

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: 413.46

Molecular Weight (Monoisotopic): 413.1045

AlogP: 1.56

#Rotatable Bonds: 4

Polar Surface Area: 112.65

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.71

CX Basic pKa: ┄

CX LogP: 1.12

CX LogD: 0.97

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.74

Np Likeness Score: -0.72

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