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

ID: ALA4789619

PubChem CID: 162669449

Max Phase: Preclinical

Molecular Formula: C19H18N4O3

Molecular Weight: 350.38

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H18N4O3/c24-15-10-8-14(9-11-15)20-19(25)23-12-4-7-16(23)18-21-17(22-26-18)13-5-2-1-3-6-13/h1-3,5-6,8-11,16,24H,4,7,12H2,(H,20,25)/t16-/m0/s1

Standard InChI Key:  AENOIPYGJSUXBL-INIZCTEOSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    9.5916  -16.4305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2544  -16.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9233  -16.4386    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6701  -15.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8496  -15.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2510  -17.7361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5828  -18.2165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8305  -18.9994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6519  -19.0044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9132  -18.2247    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1309  -19.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7882  -20.4186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2679  -21.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0861  -21.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4224  -20.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9448  -19.5839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7030  -16.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8678  -17.5006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3138  -16.1491    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0934  -16.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2538  -17.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0326  -17.4740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6485  -16.9267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4802  -16.1185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7016  -15.8647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4243  -17.1834    0.0000 O   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
M  END

Alternative Forms

1. Parent:

   

   ALA4789619

   ---

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: 350.38

Molecular Weight (Monoisotopic): 350.1379

AlogP: 3.81

#Rotatable Bonds: 3

Polar Surface Area: 91.49

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.39

CX Basic pKa: ┄

CX LogP: 3.84

CX LogD: 3.84

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.70

Np Likeness Score: -1.62

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