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

ID: ALA1946660

PubChem CID: 57381315

Max Phase: Preclinical

Molecular Formula: C16H8F5N3O3

Molecular Weight: 385.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1c(F)cc(-c2cccc(C(F)(F)F)c2)cc1F)c1nonc1O

Standard InChI:  InChI=1S/C16H8F5N3O3/c17-10-5-8(7-2-1-3-9(4-7)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:  ZEODWPRNPIYOIX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    6.1807  -11.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8956  -11.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6120  -11.5519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6091  -10.7213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8938  -10.3122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4659  -11.9643    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7518  -11.5512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0370  -11.9629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7525  -10.7262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2627  -11.6769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7547  -12.3270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2161  -13.0110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0091  -12.7835    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0371  -10.8833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4673  -10.3126    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.8954  -12.7902    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.3190  -10.3074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0353  -10.7190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7477  -10.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7451   -9.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0240   -9.0690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3146   -9.4858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4636  -10.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4663  -11.5396    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.1767  -10.2998    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.1750  -11.1250    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
  1 16  1  0
  7  8  1  0
  3 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
 20 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:

   

   ALA1946660

   N-[2,6-difluoro-4-[3-(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: -1.58

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