US8703811, 94

ID: ALA3694243

PubChem CID: 58284814

Max Phase: Preclinical

Molecular Formula: C19H21N3O2S

Molecular Weight: 355.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc2cc(OC(C)C)ccc2n1-c1ccc(C(=O)NC2CC2)s1

Standard InChI:  InChI=1S/C19H21N3O2S/c1-11(2)24-14-6-7-16-15(10-14)20-12(3)22(16)18-9-8-17(25-18)19(23)21-13-4-5-13/h6-11,13H,4-5H2,1-3H3,(H,21,23)

Standard InChI Key:  QJLVGSFMSOPURN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    3.6331   -3.6060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5548   -3.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 O   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
   -2.7248   -1.2135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6065    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8065    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7248    1.2135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1884    2.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5650    3.1910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4475    4.6864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9890    5.0368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2051    3.7579    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4130    6.4199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1419    7.3731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9247    6.6138    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3477    7.9992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8072    8.8281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5787    9.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14  8  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 15  1  0
 18 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3694243

   N-cyclopropyl-5-(2-methyl-5-propan-2-yloxybenzimidazol-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: 355.46

Molecular Weight (Monoisotopic): 355.1354

AlogP: 4.07

#Rotatable Bonds: 5

Polar Surface Area: 56.15

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.79

CX LogP: 3.50

CX LogD: 3.49

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.75

Np Likeness Score: -1.80

References

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

Source

Source(1):

• BindingDB Database