(S)-1-(2-Benzyl-3-oxoisoindoline-4-carbonyl)-4,4-difluoropyrrolidine-2-carbonitrile

ID: ALA4474579

PubChem CID: 155537130

Max Phase: Preclinical

Molecular Formula: C21H17F2N3O2

Molecular Weight: 381.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#C[C@@H]1CC(F)(F)CN1C(=O)c1cccc2c1C(=O)N(Cc1ccccc1)C2

Standard InChI:  InChI=1S/C21H17F2N3O2/c22-21(23)9-16(10-24)26(13-21)19(27)17-8-4-7-15-12-25(20(28)18(15)17)11-14-5-2-1-3-6-14/h1-8,16H,9,11-13H2/t16-/m0/s1

Standard InChI Key:  SVZJKAXGIPHYOI-INIZCTEOSA-N

Molfile:  

 
     RDKit          2D

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   31.3711  -15.6628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0814  -16.0677    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   29.3691  -14.1673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0787  -13.7579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0759  -12.9352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3673  -12.5300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6610  -13.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6623  -12.9418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8861  -12.6883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4051  -13.3482    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.8841  -14.0095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3689  -14.9845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6611  -15.3929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.0765  -15.3933    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.1647  -16.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9640  -16.3742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8260  -15.0593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6304  -14.7863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5879  -13.3470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1803  -12.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5934  -11.9337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1865  -11.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3685  -11.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9590  -11.9364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3682  -12.6413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5530  -16.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9466  -17.2992    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  8  4  1  0
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  5  6  1  0
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  4 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
  2 18  1  0
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 11 20  1  0
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 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 27 28  3  0
 16 27  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4474579

   ---

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: 381.38

Molecular Weight (Monoisotopic): 381.1289

AlogP: 3.22

#Rotatable Bonds: 3

Polar Surface Area: 64.41

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.53

CX Basic pKa: ┄

CX LogP: 2.59

CX LogD: 2.59

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.82

Np Likeness Score: -0.70

References

1. Plescia J, De Cesco S, Patrascu MB, Kurian J, Di Trani J, Dufresne C, Wahba AS, Janmamode N, Mittermaier AK, Moitessier N..  (2019)  Integrated Synthetic, Biophysical, and Computational Investigations of Covalent Inhibitors of Prolyl Oligopeptidase and Fibroblast Activation Protein α.,  62  (17): [PMID:31393718] [10.1021/acs.jmedchem.9b00642]

Source

Source(1):

• Scientific Literature