4-Hydroxy-N-[(2,3,5,6-tetrafluoro-3'-(trifluoromethoxy))biphenyl-4-yl]-1,2,5-oxadiazole-3-carboxamide

ID: ALA1946851

PubChem CID: 57381532

Max Phase: Preclinical

Molecular Formula: C16H6F7N3O4

Molecular Weight: 437.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1c(F)c(F)c(-c2cccc(OC(F)(F)F)c2)c(F)c1F)c1nonc1O

Standard InChI:  InChI=1S/C16H6F7N3O4/c17-8-7(5-2-1-3-6(4-5)29-16(21,22)23)9(18)11(20)12(10(8)19)24-14(27)13-15(28)26-30-25-13/h1-4H,(H,24,27)(H,26,28)

Standard InChI Key:  CGEIKBLLWKMFGW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   16.8402  -16.8416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8391  -17.6690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5539  -18.0819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2703  -17.6685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2675  -16.8380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5521  -16.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1243  -18.0809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4101  -17.6679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6954  -18.0795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4108  -16.8429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9210  -17.7935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4131  -18.4437    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8744  -19.1277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6674  -18.9001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6955  -17.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5537  -18.9069    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.9855  -18.0799    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.1257  -16.4293    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.5496  -15.6039    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.9773  -16.4241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6936  -16.8356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4061  -16.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4034  -15.5953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6824  -15.1856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9729  -15.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1219  -16.8313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1246  -17.6563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8404  -18.0664    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   20.4115  -18.0711    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.1167  -18.4792    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  7  1  0
 11 15  1  0
  3  4  2  0
  3 16  1  0
  7  8  1  0
  4 17  1  0
  1 18  1  0
  8  9  1  0
  6 19  1  0
  4  5  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
  5  6  2  0
 23 24  1  0
  6  1  1  0
 24 25  2  0
 25 20  1  0
  5 20  1  0
  1  2  2  0
 22 26  1  0
 11 12  2  0
 26 27  1  0
 12 13  1  0
 27 28  1  0
 13 14  1  0
 27 29  1  0
 14  9  2  0
 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1946851

   4-oxo-N-[2,3,5,6-tetrafluoro-4-[3-(trifluoromethoxy)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: 437.23

Molecular Weight (Monoisotopic): 437.0247

AlogP: 4.15

#Rotatable Bonds: 4

Polar Surface Area: 97.48

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.37

CX Basic pKa: ┄

CX LogP: 4.98

CX LogD: 3.12

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.47

Np Likeness Score: -1.16

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]

2. Sainas S, Pippione AC, Giorgis M, Lupino E, Goyal P, Ramondetti C, Buccinnà B, Piccinini M, Braga RC, Andrade CH, Andersson M, Moritzer AC, Friemann R, Mensa S, Al-Kadaraghi S, Boschi D, Lolli ML..  (2017)  Design, synthesis, biological evaluation and X-ray structural studies of potent human dihydroorotate dehydrogenase inhibitors based on hydroxylated azole scaffolds.,  129  [PMID:28235702] [10.1016/j.ejmech.2017.02.017]

Source

Source(1):

• Scientific Literature