4-Hydroxy-N-[3'-(trifluoromethyl)biphenyl-4-yl]-1,2,5-oxadiazole-3-carboxamide

ID: ALA1946657

PubChem CID: 57381312

Max Phase: Preclinical

Molecular Formula: C16H10F3N3O3

Molecular Weight: 349.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(-c2cccc(C(F)(F)F)c2)cc1)c1nonc1O

Standard InChI:  InChI=1S/C16H10F3N3O3/c17-16(18,19)11-3-1-2-10(8-11)9-4-6-12(7-5-9)20-14(23)13-15(24)22-25-21-13/h1-8H,(H,20,23)(H,22,24)

Standard InChI Key:  YMUYZQQEKZNGQM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    7.3361   -4.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3349   -5.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0497   -5.4610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7662   -5.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7633   -4.2172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0479   -3.8080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6201   -5.4601    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9060   -5.0470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1912   -5.4587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9066   -4.2220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4168   -5.1727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9089   -5.8228    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3703   -6.5068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1632   -6.2793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1913   -4.3791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4732   -3.8033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1895   -4.2148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9019   -3.8003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8992   -2.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1782   -2.5648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4687   -2.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6177   -4.2105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6204   -5.0355    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.3308   -3.7956    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.3292   -4.6208    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14  9  2  0
  2  7  1  0
 11 15  1  0
  3  4  2  0
  7  8  1  0
 16 17  2  0
 17 18  1  0
  8  9  1  0
 18 19  2  0
  4  5  1  0
 19 20  1  0
  8 10  2  0
 20 21  2  0
 21 16  1  0
  5 16  1  0
  9 11  1  0
 18 22  1  0
  2  3  1  0
 22 23  1  0
  5  6  2  0
 22 24  1  0
  6  1  1  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1946657

   4-oxo-N-[4-[3-(trifluoromethyl)phenyl]phenyl]-1,2,5-oxadiazole-3-carboxamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 349.27

Molecular Weight (Monoisotopic): 349.0674

AlogP: 3.71

#Rotatable Bonds: 3

Polar Surface Area: 88.25

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.37

CX Basic pKa: ┄

CX LogP: 3.86

CX LogD: 2.00

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.75

Np Likeness Score: -1.62

References

1. Lolli ML, Giorgis M, Tosco P, Foti A, Fruttero R, Gasco A..  (2012)  New inhibitors of dihydroorotate dehydrogenase (DHODH) based on the 4-hydroxy-1,2,5-oxadiazol-3-yl (hydroxyfurazanyl) scaffold.,  49  [PMID:22245049] [10.1016/j.ejmech.2011.12.038]

Source

Source(1):

• Scientific Literature