3-[6-fluoro-2-[4-(2-fluorophenyl)phenyl]-3-methyl-4-quinolyl]-4H-1,2,4-oxadiazol-5-one

ID: ALA4763950

PubChem CID: 162661576

Max Phase: Preclinical

Molecular Formula: C24H15F2N3O2

Molecular Weight: 415.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1c(-c2ccc(-c3ccccc3F)cc2)nc2ccc(F)cc2c1-c1noc(=O)[nH]1

Standard InChI:  InChI=1S/C24H15F2N3O2/c1-13-21(23-28-24(30)31-29-23)18-12-16(25)10-11-20(18)27-22(13)15-8-6-14(7-9-15)17-4-2-3-5-19(17)26/h2-12H,1H3,(H,28,29,30)

Standard InChI Key:  DZAOTDUJXDMXSW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
   20.5315  -12.8398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5304  -13.6593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2384  -14.0683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2367  -12.4309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9453  -12.8362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9460  -13.6552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6546  -14.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3628  -13.6514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3581  -12.8293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6490  -12.4259    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.0721  -14.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0633  -12.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7744  -12.8262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4791  -12.4140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4746  -11.5959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7594  -11.1918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0576  -11.6064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1772  -11.1828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8882  -11.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5924  -11.1747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5867  -10.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8711   -9.9535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1698  -10.3690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4580   -9.9676    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.8224  -14.0673    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.6563  -14.8794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9984  -15.3606    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.2525  -16.1372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0698  -16.1355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3206  -15.3578    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7736  -16.7994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  8 11  1  0
  9 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 15 18  1  0
 23 24  1  0
  2 25  1  0
  7 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 26  2  0
 28 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4763950

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 415.40

Molecular Weight (Monoisotopic): 415.1132

AlogP: 5.50

#Rotatable Bonds: 3

Polar Surface Area: 71.78

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.05

CX Basic pKa: 1.34

CX LogP: 6.30

CX LogD: 5.48

Aromatic Rings: 5

Heavy Atoms: 31

QED Weighted: 0.42

Np Likeness Score: -1.16

References

1. DeRatt LG,Christine Pietsch E,Tanner A,Shaffer P,Jacoby E,Wang W,Kazmi F,Zhang X,Attar RM,Edwards JP,Kuduk SD.  (2020)  A carboxylic acid isostere screen of the DHODH inhibitor Brequinar.,  30  (22): [PMID:33007394] [10.1016/j.bmcl.2020.127589]

Source

Source(1):

• Scientific Literature