US8703811, 93

ID: ALA3694242

PubChem CID: 58284867

Max Phase: Preclinical

Molecular Formula: C20H17N3OS

Molecular Weight: 347.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc2cc3ccccc3cc2n1-c1ccc(C(=O)NC2CC2)s1

Standard InChI:  InChI=1S/C20H17N3OS/c1-12-21-16-10-13-4-2-3-5-14(13)11-17(16)23(12)19-9-8-18(25-19)20(24)22-15-6-7-15/h2-5,8-11,15H,6-7H2,1H3,(H,22,24)

Standard InChI Key:  PVNHHMFKZMVEEV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 29  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    3.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2991    3.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981    3.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981    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  2  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 13  2  0
 13  4  1  0
 13 14  1  0
 14  2  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:

   

   ALA3694242

   N-cyclopropyl-5-(2-methylbenzo[f]benzimidazol-3-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: 347.44

Molecular Weight (Monoisotopic): 347.1092

AlogP: 4.44

#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: 5.23

CX LogP: 3.87

CX LogD: 3.87

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.60

Np Likeness Score: -1.42

References

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

Source

Source(1):

• BindingDB Database