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

ID: ALA4748085

PubChem CID: 118647258

Max Phase: Preclinical

Molecular Formula: C22H19F2N3O4

Molecular Weight: 427.41

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H19F2N3O4/c23-22(24,15-4-2-1-3-5-15)21(31)25-11-13-6-7-16-14(10-13)12-27(20(16)30)17-8-9-18(28)26-19(17)29/h1-7,10,17H,8-9,11-12H2,(H,25,31)(H,26,28,29)

Standard InChI Key:  XGBDIBOYKIRRPQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   30.1123  -12.9843    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   30.5250  -13.6941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9334  -12.9818    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   33.3590  -12.8769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3578  -13.6965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0659  -14.1054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0641  -12.4681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7727  -12.8733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7730  -13.6965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5559  -13.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0396  -13.2845    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.5555  -12.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8569  -13.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2645  -13.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0781  -13.9969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4903  -13.2909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0827  -12.5815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.2629  -12.5782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3075  -13.2937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.8548  -11.8702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.8078  -11.8415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.6498  -14.1045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9424  -13.6953    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.2344  -14.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8190  -14.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1150  -13.6922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4075  -14.0996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4064  -14.9176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1188  -15.3266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8234  -14.9169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2337  -14.9206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  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
 16 19  2  0
 18 20  2  0
 12 21  2  0
  5 22  1  0
 22 23  1  0
 23 24  1  0
 24  2  1  0
  2 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 24 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4748085

   ---

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: 427.41

Molecular Weight (Monoisotopic): 427.1344

AlogP: 1.86

#Rotatable Bonds: 5

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: 9.48

CX Basic pKa: ┄

CX LogP: 1.67

CX LogD: 1.66

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.71

Np Likeness Score: -0.35

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