Flubendazole

ID: ALA5188842

PubChem CID: 168280046

Max Phase: Preclinical

Molecular Formula: C17H16FN3O

Molecular Weight: 297.33

Names and Identifiers

Canonical SMILES:  CC(C)Nc1nc2cc(C(=O)c3ccc(F)cc3)ccc2[nH]1

Standard InChI:  InChI=1S/C17H16FN3O/c1-10(2)19-17-20-14-8-5-12(9-15(14)21-17)16(22)11-3-6-13(18)7-4-11/h3-10H,1-2H3,(H2,19,20,21)

Standard InChI Key:  PLIGRAOYQXJABZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -3.4361    0.5147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4361   -0.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7228   -0.7166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0156   -0.3065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0156    0.5151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7245    0.9253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3040   -0.7173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5924   -0.3065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5924    0.5152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1176    0.9242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8309    0.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8309   -0.3043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1221   -0.7191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6072   -0.5465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0935    0.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257    0.7626    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9151    0.1158    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3260    0.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1477    0.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9151    1.5391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3040   -1.5391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1477    0.9256    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  1  2  0
  4  7  1  0
  7  8  1  0
  9  8  2  0
 10  9  1  0
 11 10  2  0
 12 11  1  0
 13 12  2  0
  8 13  1  0
 12 14  1  0
 14 15  2  0
 16 15  1  0
 11 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
  7 21  2  0
  1 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5188842

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 297.33

Molecular Weight (Monoisotopic): 297.1277

AlogP: 3.75

#Rotatable Bonds: 4

Polar Surface Area: 57.78

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.86

CX Basic pKa: 6.10

CX LogP: 3.79

CX LogD: 3.77

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.72

Np Likeness Score: -1.22

References

1. Hawryluk N, Robinson D, Shen Y, Kyne G, Bedore M, Menon S, Canan S, von Geldern T, Townson S, Gokool S, Ehrens A, Koschel M, Lhermitte-Vallarino N, Martin C, Hoerauf A, Hernandez G, Dalvie D, Specht S, Hübner MP, Scandale I..  (2022)  Discovery of Substituted Di(pyridin-2-yl)-1,2,4-thiadiazol-5-amines as Novel Macrofilaricidal Compounds for the Treatment of Human Filarial Infections.,  65  (16.0): [PMID:35972896] [10.1021/acs.jmedchem.2c00960]

Source

Source(1):

• Scientific Literature