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

ID: ALA1946656

PubChem CID: 57381311

Max Phase: Preclinical

Molecular Formula: C16H10F3N3O3

Molecular Weight: 349.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(-c2ccc(C(F)(F)F)cc2)cc1)c1nonc1O

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

Standard InChI Key:  NKEASJIPNFEXOM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -1.9984   -5.4190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2836   -5.8319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5672   -5.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5700   -4.5880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2854   -4.1789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7132   -5.8309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4274   -5.4179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1421   -5.8295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4267   -4.5929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9165   -5.5435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4244   -6.1937    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9631   -6.8777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1701   -6.6501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1420   -4.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1398   -4.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8561   -4.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5686   -4.1711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5659   -3.3453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8449   -2.9356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1354   -3.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2783   -2.9291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9948   -3.3380    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.2741   -2.1041    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.9875   -2.5083    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
 19 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:

   

   ALA1946656

   4-oxo-N-[4-[4-(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: -1.43

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