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

ID: ALA4795754

PubChem CID: 162673625

Max Phase: Preclinical

Molecular Formula: C21H23N5O4S

Molecular Weight: 441.51

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN(C)S(=O)(=O)c1ccc(NC(=O)N2CCC[C@H]2c2nc(-c3ccccc3)no2)cc1

Standard InChI:  InChI=1S/C21H23N5O4S/c1-25(2)31(28,29)17-12-10-16(11-13-17)22-21(27)26-14-6-9-18(26)20-23-19(24-30-20)15-7-4-3-5-8-15/h3-5,7-8,10-13,18H,6,9,14H2,1-2H3,(H,22,27)/t18-/m0/s1

Standard InChI Key:  SRBHKBOKOKVAST-SFHVURJKSA-N

Molfile:  

 
     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   39.0518  -17.4912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.8413  -18.2836    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   39.6329  -18.0697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.0343  -17.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6930  -18.0161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3577  -17.5406    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.1086  -16.7596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2923  -16.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6895  -18.8340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0255  -19.3103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.2732  -20.0890    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.0904  -20.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3476  -19.3184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.5653  -20.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2267  -21.5040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7023  -22.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5164  -22.0834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8527  -21.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3750  -20.6735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1333  -17.7981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2980  -18.5985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.7440  -17.2552    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.5196  -17.5127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6799  -18.3142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4546  -18.5718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0664  -18.0286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8981  -17.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1236  -16.9708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0081  -19.0853    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.7842  -19.3412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3985  -19.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  4  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13  9  2  0
  5  9  1  6
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 12 14  1  0
  6 20  1  0
 20 21  2  0
 20 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
 26  2  1  0
  2 29  1  0
 29 30  1  0
 29 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4795754

   ---

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: 441.51

Molecular Weight (Monoisotopic): 441.1471

AlogP: 3.36

#Rotatable Bonds: 5

Polar Surface Area: 108.64

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.49

CX Basic pKa: ┄

CX LogP: 3.26

CX LogD: 3.26

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.65

Np Likeness Score: -2.21

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