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

ID: ALA4782333

PubChem CID: 7294555

Max Phase: Preclinical

Molecular Formula: C19H17ClN4O2

Molecular Weight: 368.82

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(Cl)cc1)N1CCC[C@@H]1c1nc(-c2ccccc2)no1

Standard InChI:  InChI=1S/C19H17ClN4O2/c20-14-8-10-15(11-9-14)21-19(25)24-12-4-7-16(24)18-22-17(23-26-18)13-5-2-1-3-6-13/h1-3,5-6,8-11,16H,4,7,12H2,(H,21,25)/t16-/m1/s1

Standard InChI Key:  AXXUHIDVIKIKLD-MRXNPFEDSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   28.1517   -5.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8146   -5.9811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4834   -5.5056    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.2302   -4.7205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4098   -4.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8111   -6.8031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1429   -7.2835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3907   -8.0664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.2120   -8.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4733   -7.2917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.6910   -8.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3483   -9.4855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8280  -10.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6463  -10.0690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9825   -9.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5049   -8.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2631   -5.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4279   -6.5676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.8739   -5.2160    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.6536   -5.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8139   -6.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5928   -6.5409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2086   -5.9936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0404   -5.1855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2617   -4.9317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9844   -6.2503    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  1
 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
M  END

Alternative Forms

1. Parent:

   

   ALA4782333

   (2R)-N-(4-chlorophenyl)-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: 368.82

Molecular Weight (Monoisotopic): 368.1040

AlogP: 4.76

#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: 13.31

CX Basic pKa: ┄

CX LogP: 4.69

CX LogD: 4.69

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.72

Np Likeness Score: -2.08

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