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

ID: ALA4790279

PubChem CID: 95057764

Max Phase: Preclinical

Molecular Formula: C20H19ClN4O3

Molecular Weight: 398.85

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cccc(-c2noc([C@@H]3CCCN3C(=O)Nc3ccc(Cl)cc3)n2)c1

Standard InChI:  InChI=1S/C20H19ClN4O3/c1-27-16-5-2-4-13(12-16)18-23-19(28-24-18)17-6-3-11-25(17)20(26)22-15-9-7-14(21)8-10-15/h2,4-5,7-10,12,17H,3,6,11H2,1H3,(H,22,26)/t17-/m0/s1

Standard InChI Key:  CCFGTVGNQOBGSR-KRWDZBQOSA-N

Molfile:  

 
     RDKit          2D

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    9.4885   -9.9598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1609   -9.4817    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9063   -8.6924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0815   -8.6912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4849  -10.7863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8131  -11.2693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0622  -12.0564    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8880  -12.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1507  -11.2774    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3696  -12.7300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0251  -13.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5074  -14.1504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3300  -14.0699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6681  -13.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1879  -12.6440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9448   -9.7406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1105  -10.5495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5589   -9.1906    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3428   -9.4537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5040  -10.2637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2870  -10.5226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9063   -9.9724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7372   -9.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9542   -8.9047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6863  -10.2305    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.4855  -13.2288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9664  -13.8949    0.0000 C   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
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  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
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 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 23 26  1  0
 15 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4790279

   (2S)-N-(4-chlorophenyl)-2-[3-(3-methoxyphenyl)-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: 398.85

Molecular Weight (Monoisotopic): 398.1146

AlogP: 4.77

#Rotatable Bonds: 4

Polar Surface Area: 80.49

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.31

CX Basic pKa: ┄

CX LogP: 4.49

CX LogD: 4.49

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.68

Np Likeness Score: -2.01

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