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

ID: ALA1946659

Cas Number: 1364791-93-4

PubChem CID: 57381314

Max Phase: Preclinical

Molecular Formula: C15H7F4N3O3

Molecular Weight: 353.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1c(F)c(F)c(-c2ccccc2)c(F)c1F)c1nonc1O

Standard InChI:  InChI=1S/C15H7F4N3O3/c16-8-7(6-4-2-1-3-5-6)9(17)11(19)12(10(8)18)20-14(23)13-15(24)22-25-21-13/h1-5H,(H,20,23)(H,22,24)

Standard InChI Key:  AMBZERWHSFYQLK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   -1.8431  -10.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8443  -11.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1294  -11.8235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4130  -11.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4159  -10.5797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1312  -10.1705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5591  -11.8226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2732  -11.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9880  -11.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2725  -10.5845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7623  -11.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2703  -12.1853    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8089  -12.8693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0159  -12.6418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9879  -10.7416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5577  -10.1710    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1296  -12.6485    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.3021  -11.8216    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1337   -9.3455    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.2940  -10.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0103  -10.5773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7227  -10.1628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7201   -9.3369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9990   -8.9273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2896   -9.3442    0.0000 C   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
  1 16  1  0
  7  8  1  0
  3 17  1  0
  4 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
M  END

Alternative Forms

1. Parent:

   

   ALA1946659

   Dhodh-IN-14

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: 353.23

Molecular Weight (Monoisotopic): 353.0424

AlogP: 3.25

#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: 3.55

CX LogD: 1.69

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.56

Np Likeness Score: -1.10

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