N-((2-(2,6-Dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)-methyl)benzamide

ID: ALA4742231

PubChem CID: 44539606

Max Phase: Preclinical

Molecular Formula: C21H19N3O4

Molecular Weight: 377.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1CCC(N2Cc3cc(CNC(=O)c4ccccc4)ccc3C2=O)C(=O)N1

Standard InChI:  InChI=1S/C21H19N3O4/c25-18-9-8-17(20(27)23-18)24-12-15-10-13(6-7-16(15)21(24)28)11-22-19(26)14-4-2-1-3-5-14/h1-7,10,17H,8-9,11-12H2,(H,22,26)(H,23,25,27)

Standard InChI Key:  IKUDMBCBGPFJRR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   32.4097   -7.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4086   -8.3847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1166   -8.7937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1148   -7.1563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8234   -7.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8237   -8.3847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6067   -8.6389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0904   -7.9728    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.6063   -7.3070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9076   -7.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3153   -8.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1289   -8.6852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5411   -7.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1334   -7.2697    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.3136   -7.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3582   -7.9819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.9055   -6.5584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.8585   -6.5298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.7005   -8.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9931   -8.3836    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.2851   -8.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5777   -8.3825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2845   -9.6088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.5831   -7.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8766   -7.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1676   -7.5633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1696   -8.3847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8767   -8.7901    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
 13 16  2  0
 15 17  2  0
  9 18  2  0
  2 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 22 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4742231

   N-[2-(2,6-dioxo-piperidin-3-yl)-1-oxo-2,3-dihydro-1H-isoindol-5-ylmethyl]-benzamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 377.40

Molecular Weight (Monoisotopic): 377.1376

AlogP: 1.38

#Rotatable Bonds: 4

Polar Surface Area: 95.58

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.61

CX Basic pKa: ┄

CX LogP: 0.92

CX LogD: 0.92

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.79

Np Likeness Score: -0.40

References

1. Hansen JD,Correa M,Alexander M,Nagy M,Huang D,Sapienza J,Lu G,LeBrun LA,Cathers BE,Zhang W,Tang Y,Ammirante M,Narla RK,Piccotti JR,Pourdehnad M,Lopez-Girona A.  (2021)  CC-90009: A Cereblon E3 Ligase Modulating Drug That Promotes Selective Degradation of GSPT1 for the Treatment of Acute Myeloid Leukemia.,  64  (4.0): [PMID:33591756] [10.1021/acs.jmedchem.0c01489]

Source

Source(1):

• Scientific Literature