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

ID: ALA1946848

PubChem CID: 57381529

Max Phase: Preclinical

Molecular Formula: C16H8F5N3O3

Molecular Weight: 385.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1c(F)cc(-c2ccc(C(F)(F)F)cc2)cc1F)c1nonc1O

Standard InChI:  InChI=1S/C16H8F5N3O3/c17-10-5-8(7-1-3-9(4-2-7)16(19,20)21)6-11(18)12(10)22-14(25)13-15(26)24-27-23-13/h1-6H,(H,22,25)(H,24,26)

Standard InChI Key:  OGZFCOSJXCOOPX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   16.3527  -10.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3516  -10.9482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0664  -11.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7828  -10.9477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7800  -10.1172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0646   -9.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6368  -11.3601    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9226  -10.9470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2079  -11.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9233  -10.1220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4335  -11.0727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9256  -11.7228    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3869  -12.4068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1799  -12.1793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2080  -10.2791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0662  -12.1860    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.6382   -9.7085    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.4898   -9.7033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2061  -10.1148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9186   -9.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9159   -8.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1949   -8.4648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4854   -8.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6283   -8.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3448   -8.8671    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   20.6241   -7.6333    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.3375   -8.0375    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  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
  3 16  1  0
  7  8  1  0
  1 17  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
  9 11  1  0
 21 22  1  0
  2  3  1  0
 22 23  2  0
 23 18  1  0
  5 18  1  0
  5  6  2  0
 21 24  1  0
  6  1  1  0
 24 25  1  0
  1  2  2  0
 24 26  1  0
 11 12  2  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1946848

   N-[2,6-difluoro-4-[4-(trifluoromethyl)phenyl]phenyl]-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: 385.25

Molecular Weight (Monoisotopic): 385.0486

AlogP: 3.99

#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: 4.14

CX LogD: 2.28

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.67

Np Likeness Score: -1.45

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