US8703811, 91

ID: ALA3694240

PubChem CID: 58284883

Max Phase: Preclinical

Molecular Formula: C17H16FN3O

Molecular Weight: 297.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCNC(=O)c1ccc(-n2c(C)nc3cc(F)ccc32)cc1

Standard InChI:  InChI=1S/C17H16FN3O/c1-3-19-17(22)12-4-7-14(8-5-12)21-11(2)20-15-10-13(18)6-9-16(15)21/h4-10H,3H2,1-2H3,(H,19,22)

Standard InChI Key:  IAZDRWAHHDMWAI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -7.6289   -7.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4777   -7.7931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3902   -6.7589    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9504   -7.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6687   -8.3492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8628   -6.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4233   -6.5700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3384   -5.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6928   -4.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1327   -3.6551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2175   -4.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3114   -2.9665    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8032   -3.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4032   -4.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4133   -1.7530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.7000    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 22 12  1  0
 22 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3694240

   N-ethyl-4-(5-fluoro-2-methylbenzimidazol-1-yl)benzamide

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: 297.33

Molecular Weight (Monoisotopic): 297.1277

AlogP: 3.22

#Rotatable Bonds: 3

Polar Surface Area: 46.92

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.49

CX LogP: 2.84

CX LogD: 2.83

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.81

Np Likeness Score: -2.11

References

1.  (2014)  Small molecule inhibitors of Plasmodium falciparum dihydroorotate dehydrogenase, 

Source

Source(1):

• BindingDB Database