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

ID: ALA4749221

PubChem CID: 162651960

Max Phase: Preclinical

Molecular Formula: C22H21N3O4

Molecular Weight: 391.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Cc1ccccc1)NCc1ccc2c(c1)CN(C1CCC(=O)NC1=O)C2=O

Standard InChI:  InChI=1S/C22H21N3O4/c26-19-9-8-18(21(28)24-19)25-13-16-10-15(6-7-17(16)22(25)29)12-23-20(27)11-14-4-2-1-3-5-14/h1-7,10,18H,8-9,11-13H2,(H,23,27)(H,24,26,28)

Standard InChI Key:  CGGOJJPTDGHQBH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   18.8146   -7.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8135   -8.3393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5215   -8.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5197   -7.1109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2283   -7.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2286   -8.3393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0116   -8.5935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4953   -7.9274    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0112   -7.2616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3126   -7.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7202   -8.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5338   -8.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9460   -7.9337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5384   -7.2243    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.7186   -7.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7632   -7.9365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3104   -6.5130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2634   -6.4844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1054   -8.7473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3981   -8.3382    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6900   -8.7462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9826   -8.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2746   -8.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5707   -8.3351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8631   -8.7424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8621   -9.5605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5744   -9.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2790   -9.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6894   -9.5634    0.0000 O   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
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 21 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4749221

   ---

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: 391.43

Molecular Weight (Monoisotopic): 391.1532

AlogP: 1.31

#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: 11.61

CX Basic pKa: ┄

CX LogP: 0.90

CX LogD: 0.90

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.75

Np Likeness Score: -0.39

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