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

ID: ALA1946658

PubChem CID: 57381313

Max Phase: Preclinical

Molecular Formula: C15H9F2N3O3

Molecular Weight: 317.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1c(F)cc(-c2ccccc2)cc1F)c1nonc1O

Standard InChI:  InChI=1S/C15H9F2N3O3/c16-10-6-9(8-4-2-1-3-5-8)7-11(17)12(10)18-14(21)13-15(22)20-23-19-13/h1-7H,(H,18,21)(H,20,22)

Standard InChI Key:  MDNBGOKZECKOET-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   18.7694   -3.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7682   -4.5773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4831   -4.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1995   -4.5769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1966   -3.7463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4813   -3.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0534   -4.9893    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3393   -4.5762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6245   -4.9879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3400   -3.7512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8502   -4.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3422   -5.3520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8036   -6.0360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5966   -5.8085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6246   -3.9083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9065   -3.3324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6228   -3.7440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3352   -3.3295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3326   -2.5036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6115   -2.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9021   -2.5108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4829   -5.8152    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.0548   -3.3376    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  2  0
  6  1  1  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
  3 22  1  0
  2  3  1  0
  1 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1946658

   N-(2,6-difluoro-4-phenylphenyl)-4-oxo-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: 317.25

Molecular Weight (Monoisotopic): 317.0612

AlogP: 2.97

#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: 3.26

CX LogD: 1.41

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.78

Np Likeness Score: -1.40

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