US8703811, 95

ID: ALA3694244

PubChem CID: 58284877

Max Phase: Preclinical

Molecular Formula: C16H13F2N3OS

Molecular Weight: 333.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc2cc(F)c(F)cc2n1-c1ccc(C(=O)NC2CC2)s1

Standard InChI:  InChI=1S/C16H13F2N3OS/c1-8-19-12-6-10(17)11(18)7-13(12)21(8)15-5-4-14(23-15)16(22)20-9-2-3-9/h4-7,9H,2-3H2,1H3,(H,20,22)

Standard InChI Key:  FBZQWYOZXKENJW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
    2.4032   -4.1625    0.0000 C   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
    2.4133   -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
   -2.3383    1.3500    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
    0.0000   -1.5000    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
   -0.6928   -4.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1742   -4.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6753   -5.4380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4855   -6.3515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2491   -5.5022    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5220   -7.8493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5757   -8.4234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2414   -8.6319    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2780  -10.1323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4398  -11.3594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0597  -11.3196    0.0000 C   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  7  1  0
  6  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11  4  1  0
 11 12  1  0
 12  2  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 13  1  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3694244

   N-cyclopropyl-5-(5,6-difluoro-2-methylbenzimidazol-1-yl)thiophene-2-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: 333.36

Molecular Weight (Monoisotopic): 333.0747

AlogP: 3.57

#Rotatable Bonds: 3

Polar Surface Area: 46.92

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.57

CX LogP: 3.17

CX LogD: 3.16

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.80

Np Likeness Score: -1.94

References

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

Source

Source(1):

• BindingDB Database