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

ID: ALA1946653

Cas Number: 1364791-86-5

PubChem CID: 57381308

Max Phase: Preclinical

Molecular Formula: C10H6F3N3O3

Molecular Weight: 273.17

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C10H6F3N3O3/c11-10(12,13)5-1-3-6(4-2-5)14-8(17)7-9(18)16-19-15-7/h1-4H,(H,14,17)(H,16,18)

Standard InChI Key:  SYZRMPPEMZWUSK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
   -1.2598    1.4959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2609    0.6685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5461    0.2556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1703    0.6690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1675    1.4995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5479    1.9086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9757    0.2566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899    0.6696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4046    0.2580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6892    1.4946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1790    0.5440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6869   -0.1062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2256   -0.7902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4326   -0.5626    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4045    1.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8804    1.9147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5964    1.5049    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.8773    2.7397    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.5917    2.3333    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  8 10  2  0
  9 11  1  0
  2  3  1  0
  5  6  2  0
  6  1  1  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
  5 16  1  0
  7  8  1  0
 16 17  1  0
 16 18  1  0
  8  9  1  0
 16 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1946653

   Dhodh-IN-13

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: 273.17

Molecular Weight (Monoisotopic): 273.0361

AlogP: 2.05

#Rotatable Bonds: 2

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: 2.21

CX LogD: 0.35

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.87

Np Likeness Score: -1.81

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