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

ID: ALA4795413

PubChem CID: 7481960

Max Phase: Preclinical

Molecular Formula: C19H17BrN4O2

Molecular Weight: 413.27

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1cccc(Br)c1)N1CCC[C@H]1c1nc(-c2ccccc2)no1

Standard InChI:  InChI=1S/C19H17BrN4O2/c20-14-8-4-9-15(12-14)21-19(25)24-11-5-10-16(24)18-22-17(23-26-18)13-6-2-1-3-7-13/h1-4,6-9,12,16H,5,10-11H2,(H,21,25)/t16-/m0/s1

Standard InChI Key:  KACUQNALDUKPRH-INIZCTEOSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    0.7758   -1.3496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4346   -1.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1034   -1.3577    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8543   -0.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0339   -0.5714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4311   -2.6552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7670   -3.1356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0148   -3.9185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8361   -3.9235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0933   -3.1438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3110   -4.5886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9724   -5.3418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4521   -6.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -5.9212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6066   -5.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1249   -4.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8831   -1.6152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0479   -2.4198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4980   -1.0682    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2777   -1.3298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4380   -2.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2169   -2.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8327   -1.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645   -1.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8858   -0.7838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2733   -0.4926    0.0000 Br  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
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4795413

   (2S)-N-(3-bromophenyl)-2-(3-phenyl-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: 413.27

Molecular Weight (Monoisotopic): 412.0535

AlogP: 4.87

#Rotatable Bonds: 3

Polar Surface Area: 71.26

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.09

CX Basic pKa: ┄

CX LogP: 4.89

CX LogD: 4.89

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.67

Np Likeness Score: -2.05

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