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

ID: ALA1946655

PubChem CID: 57381310

Max Phase: Preclinical

Molecular Formula: C15H11N3O3

Molecular Weight: 281.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccccc1-c1ccccc1)c1nonc1O

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

Standard InChI Key:  ZNKLZJHDLNMUCB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   16.1111    2.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1099    1.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8247    0.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5412    1.1773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5383    2.0078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8229    2.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3951    0.7649    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6810    1.1780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9662    0.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6816    2.0030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1918    1.0523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6839    0.4022    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1453   -0.2818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9382   -0.0543    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9663    1.8459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8264   -0.0588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1102   -0.4706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1097   -1.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8246   -1.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5415   -1.2915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5385   -0.4687    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
  3 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1946655

   4-oxo-N-(2-phenylphenyl)-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: 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