US8703811, 12

ID: ALA3690111

PubChem CID: 44480862

Max Phase: Preclinical

Molecular Formula: C16H17N3OS

Molecular Weight: 299.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCNC(=O)c1ccc(-n2c(C)nc3ccccc32)s1

Standard InChI:  InChI=1S/C16H17N3OS/c1-3-10-17-16(20)14-8-9-15(21-14)19-11(2)18-12-6-4-5-7-13(12)19/h4-9H,3,10H2,1-2H3,(H,17,20)

Standard InChI Key:  KBBUJPFPTIFZBX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   -8.8558   -3.2631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6658   -3.1088    0.0000 C   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
   -5.2654   -4.1077    0.0000 N   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
   -4.8143   -6.4075    0.0000 O   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
    2.4032   -4.1625    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  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11  7  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 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 12  1  0
 21 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3690111

   5-(2-methyl-1h-benzimidazol-1-yl)-N-propylthiophene-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: 299.40

Molecular Weight (Monoisotopic): 299.1092

AlogP: 3.54

#Rotatable Bonds: 4

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: 5.35

CX LogP: 3.30

CX LogD: 3.29

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.80

Np Likeness Score: -1.89

References

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

Source

Source(1):

• BindingDB Database