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

ID: ALA4791236

PubChem CID: 7237768

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(-c2cccc(Cl)c2)no1

Standard InChI:  InChI=1S/C19H16Cl2N4O2/c20-13-6-8-15(9-7-13)22-19(26)25-10-2-5-16(25)18-23-17(24-27-18)12-3-1-4-14(21)11-12/h1,3-4,6-9,11,16H,2,5,10H2,(H,22,26)/t16-/m0/s1

Standard InChI Key:  IACPIXDWEXUXKP-INIZCTEOSA-N

Molfile:  

 
     RDKit          2D

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   24.7357   -1.4690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4022   -1.9552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0746   -1.4772    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.8200   -0.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9952   -0.6865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3986   -2.7817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7268   -3.2647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9760   -4.0517    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.8017   -4.0569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0644   -3.2728    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.2833   -4.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9388   -5.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4211   -6.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2438   -6.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5818   -5.3076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1016   -4.6394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8585   -1.7361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0242   -2.5449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4726   -1.1860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.2566   -1.4490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4177   -2.2591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2007   -2.5181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8200   -1.9678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6509   -1.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8679   -0.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6000   -2.2259    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   28.3992   -5.2243    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
 15 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4791236

   (2S)-N-(4-chlorophenyl)-2-[3-(3-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: -2.16

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