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

ID: ALA2012942

PubChem CID: 70695831

Max Phase: Preclinical

Molecular Formula: C17H18N4OS

Molecular Weight: 326.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)c1nc2ccccc2n1-c1ccc(C(=O)NC2CC2)s1

Standard InChI:  InChI=1S/C17H18N4OS/c1-20(2)17-19-12-5-3-4-6-13(12)21(17)15-10-9-14(23-15)16(22)18-11-7-8-11/h3-6,9-11H,7-8H2,1-2H3,(H,18,22)

Standard InChI Key:  OCWAYGPQFPSDJP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   -3.0977    0.9219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3082    1.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6477    0.6636    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9711    1.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2116    1.9258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367    1.9409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7600    1.4220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4365    0.9493    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3708    0.1446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1956    0.1608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6202   -0.5442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2211   -1.2660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3932   -1.2783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9723   -0.5725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1910    0.8668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0343    0.0563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4325    1.4076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7458   -0.2132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7446    2.2472    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0223    2.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4516    2.6730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2843   -0.8330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5538   -0.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
  5  6  1  0
 11 12  2  0
  6  2  2  0
 12 13  1  0
  1  7  1  0
 13 14  2  0
 14  9  1  0
  1  2  1  0
  4 15  1  0
  2  3  1  0
 15 16  1  0
  7  8  2  0
 15 17  2  0
  8 10  1  0
 16 18  1  0
  9  1  1  0
  7 19  1  0
 19 20  1  0
  3  4  1  0
 19 21  1  0
 22 18  1  0
 23 22  1  0
 18 23  1  0
  9 10  2  0
  4  5  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2012942

   N-cyclopropyl-5-[2-(dimethylamino)benzimidazol-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: 326.43

Molecular Weight (Monoisotopic): 326.1201

AlogP: 3.05

#Rotatable Bonds: 4

Polar Surface Area: 50.16

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.12

CX LogP: 3.55

CX LogD: 3.55

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.80

Np Likeness Score: -1.61

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]

Source

Source(1):

• Scientific Literature