5-(1H-benzo[d]imidazol-1-yl)-N-cyclobutylthiophene-2-carboxamide

ID: ALA2012825

PubChem CID: 58284878

Max Phase: Preclinical

Molecular Formula: C16H15N3OS

Molecular Weight: 297.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NC1CCC1)c1ccc(-n2cnc3ccccc32)s1

Standard InChI:  InChI=1S/C16H15N3OS/c20-16(18-11-4-3-5-11)14-8-9-15(21-14)19-10-17-12-6-1-2-7-13(12)19/h1-2,6-11H,3-5H2,(H,18,20)

Standard InChI Key:  WREVZKANZSJFPC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 24  0  0  0  0  0  0  0  0999 V2000
   -4.8143   -6.4075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3533   -5.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2654   -4.1077    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7537   -4.3007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8926   -3.3810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8056   -4.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6155   -5.4841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8675   -5.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8348   -6.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4810   -5.5489    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
   -2.1519   -3.7886    0.0000 S   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
    2.4133   -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
   -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  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  4  1  0
  2  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12  8  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 13  1  0
 21 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2012825

   5-(benzimidazol-1-yl)-N-cyclobutylthiophene-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: 297.38

Molecular Weight (Monoisotopic): 297.0936

AlogP: 3.37

#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: 4.76

CX LogP: 3.20

CX LogD: 3.20

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.81

Np Likeness Score: -1.63

References

1. Skerlj RT, Bastos CM, Booker ML, Kramer ML, Barker RH, Celatka CA, O'Shea TJ, Munoz B, Sidhu AB, Cortese JF, Wittlin S, Papastogiannidis P, Angulo-Barturen I, Jimenez-Diaz MB, Sybertz E..  (2011)  Optimization of Potent Inhibitors of P. falciparum Dihydroorotate Dehydrogenase for the Treatment of Malaria.,  2  (9): [PMID:24900364] [10.1021/ml200143c]

2.  (2014)  Small molecule inhibitors of Plasmodium falciparum dihydroorotate dehydrogenase, 

Source

Source(2):

• Scientific Literature
• BindingDB Database