(S)-N-(4-chlorophenyl)-2-(3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboxamide

ID: ALA4791315

PubChem CID: 7361765

Max Phase: Preclinical

Molecular Formula: C19H16Cl2N4O2

Molecular Weight: 403.27

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(Cl)cc1)N1CCC[C@H]1c1nc(-c2ccc(Cl)cc2)no1

Standard InChI:  InChI=1S/C19H16Cl2N4O2/c20-13-5-3-12(4-6-13)17-23-18(27-24-17)16-2-1-11-25(16)19(26)22-15-9-7-14(21)8-10-15/h3-10,16H,1-2,11H2,(H,22,26)/t16-/m0/s1

Standard InChI Key:  VLKRJQUYGJVMDV-INIZCTEOSA-N

Molfile:  

 
     RDKit          2D

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    0.9794  -16.7869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6458  -17.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3183  -16.7950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0637  -16.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2388  -16.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6423  -18.0997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9704  -18.5827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2196  -19.3698    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0454  -19.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3082  -18.5909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5271  -20.0436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1825  -20.7969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6648  -21.4641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4876  -21.3836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8257  -20.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3455  -19.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1023  -17.0539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2680  -17.8629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7165  -16.5038    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5005  -16.7668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6617  -17.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4449  -17.8360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0641  -17.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8950  -16.4731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1120  -16.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8442  -17.5438    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9680  -22.0502    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10  6  2  0
  2  6  1  6
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  9 11  1  0
  3 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 23 26  1  0
 14 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4791315

   (2S)-N-(4-chlorophenyl)-2-[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carboxamide

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: 403.27

Molecular Weight (Monoisotopic): 402.0650

AlogP: 5.41

#Rotatable Bonds: 3

Polar Surface Area: 71.26

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.31

CX Basic pKa: ┄

CX LogP: 5.25

CX LogD: 5.25

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.63

Np Likeness Score: -1.94

References

1. Ruan B,Zhang Y,Tadesse S,Preston S,Taki AC,Jabbar A,Hofmann A,Jiao Y,Garcia-Bustos J,Harjani J,Le TG,Varghese S,Teguh S,Xie Y,Odiba J,Hu M,Gasser RB,Baell J.  (2020)  Synthesis and structure-activity relationship study of pyrrolidine-oxadiazoles as anthelmintics against Haemonchus contortus.,  190  [PMID:32018095] [10.1016/j.ejmech.2020.112100]

Source

Source(1):

• Scientific Literature