2-(2,6-Dioxopiperidin-3-yl)-4-((2-(2-(2-methoxyethoxy)ethoxy)ethyl)amino)isoindoline-1,3-dione

ID: ALA5195174

PubChem CID: 139441794

Max Phase: Preclinical

Molecular Formula: C20H25N3O7

Molecular Weight: 419.43

Names and Identifiers

Canonical SMILES:  COCCOCCOCCNc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O

Standard InChI:  InChI=1S/C20H25N3O7/c1-28-9-10-30-12-11-29-8-7-21-14-4-2-3-13-17(14)20(27)23(19(13)26)15-5-6-16(24)22-18(15)25/h2-4,15,21H,5-12H2,1H3,(H,22,24,25)

Standard InChI Key:  RPYMUKUTWBEVRQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    3.6106   -3.1950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1949   -2.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3699   -2.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9564   -3.1950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3722   -3.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2014   -3.9125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9586   -4.6264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1314   -3.1950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6430   -3.8673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1471   -3.6104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8979   -1.7384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8632   -2.3605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5793   -2.7796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5793   -3.6094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8632   -1.5355    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5777   -1.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5777   -0.2981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2922    0.1144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2922    0.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0066    1.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0066    2.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7210    2.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7210    3.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4356    3.8269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4356    4.6519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8978   -4.6519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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  4  3  1  0
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  9 13  1  0
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 12 15  1  0
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 17 18  2  0
 11 18  1  0
 19 15  1  0
 20 19  1  0
 20 21  1  0
 22 21  1  0
 23 22  1  0
 23 24  1  0
 25 24  1  0
 26 25  1  0
 26 27  1  0
 28 27  1  0
 29 28  1  0
 10 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5195174

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 419.43

Molecular Weight (Monoisotopic): 419.1693

AlogP: 0.18

#Rotatable Bonds: 11

Polar Surface Area: 123.27

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.59

CX Basic pKa: 1.29

CX LogP: 0.00

CX LogD: 0.00

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.38

Np Likeness Score: -0.70

References

1. Zhu CL, Luo X, Tian T, Rao Z, Wang H, Zhou Z, Mi T, Chen D, Xu Y, Wu Y, Che J, Zhou Y, Li J, Dong X..  (2022)  Structure-based rational design enables efficient discovery of a new selective and potent AKT PROTAC degrader.,  238  [PMID:35635954] [10.1016/j.ejmech.2022.114459]

Source

Source(1):

• Scientific Literature