4-Hydroxy-N-(biphenyl-4-yl)-1,2,5-oxadiazole-3-carboxamide

ID: ALA1946654

Cas Number: 1364791-88-7

PubChem CID: 57381309

Max Phase: Preclinical

Molecular Formula: C15H11N3O3

Molecular Weight: 281.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(-c2ccccc2)cc1)c1nonc1O

Standard InChI:  InChI=1S/C15H11N3O3/c19-14(13-15(20)18-21-17-13)16-12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9H,(H,16,19)(H,18,20)

Standard InChI Key:  AIEVBDCDOIKIIK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    6.7402    1.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7391    0.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4539    0.3973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1703    0.8106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1675    1.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4521    2.0503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0243    0.3982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3101    0.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5954    0.3996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3108    1.6363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8210    0.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3131    0.0355    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7744   -0.6485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5674   -0.4210    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5955    1.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8809    2.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5973    1.6415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3097    2.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3070    2.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5860    3.2915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8765    2.8746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  7  8  1  0
 16 17  2  0
 17 18  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
 21 16  1  0
  5 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1946654

   Dhodh-IN-15

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: 281.27

Molecular Weight (Monoisotopic): 281.0800

AlogP: 2.69

#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: 2.98

CX LogD: 1.12

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.77

Np Likeness Score: -1.30

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