N-Cyclopropyl-5-(2-propyl-1H-benzo[d]imidazol-1-yl)thiophene-2-carboxamide

ID: ALA2012831

PubChem CID: 58284898

Max Phase: Preclinical

Molecular Formula: C18H19N3OS

Molecular Weight: 325.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCc1nc2ccccc2n1-c1ccc(C(=O)NC2CC2)s1

Standard InChI:  InChI=1S/C18H19N3OS/c1-2-5-16-20-13-6-3-4-7-14(13)21(16)17-11-10-15(23-17)18(22)19-12-8-9-12/h3-4,6-7,10-12H,2,5,8-9H2,1H3,(H,19,22)

Standard InChI Key:  WLURKKZKBITTHW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
    4.6580   -5.4551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0559   -4.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5551   -4.4192    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
   -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
    0.3114   -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  1  0
  3  4  1  0
  4  5  2  0
  5  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
 11 12  1  0
 12  4  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:

   

   ALA2012831

   N-cyclopropyl-5-(2-propylbenzimidazol-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: 325.44

Molecular Weight (Monoisotopic): 325.1249

AlogP: 3.93

#Rotatable Bonds: 5

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: 5.20

CX LogP: 4.03

CX LogD: 4.03

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.77

Np Likeness Score: -1.75

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