US8703811, 82

ID: ALA3694232

PubChem CID: 58284906

Max Phase: Preclinical

Molecular Formula: C20H16N4S

Molecular Weight: 344.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1c(-c2ccc(-c3nc4ccccc4n3C)s2)nc2ccccc21

Standard InChI:  InChI=1S/C20H16N4S/c1-23-15-9-5-3-7-13(15)21-19(23)17-11-12-18(25-17)20-22-14-8-4-6-10-16(14)24(20)2/h3-12H,1-2H3

Standard InChI Key:  RYUCIOYLAHJCPK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 29  0  0  0  0  0  0  0  0999 V2000
   -0.4916   -3.8582    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
    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
    2.5536   -4.4230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0412   -5.8141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2310   -6.7275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4674   -5.8782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0417   -4.4398    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.8820   -6.3795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0247   -5.4261    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2815   -6.2435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7306   -5.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7907   -6.9171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4018   -8.3658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9527   -8.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8926   -7.6922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3954   -7.7702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7353   -8.7723    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  2  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  2  1  0
 10  5  1  0
  3 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 11  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 23 24  1  0
 24 16  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3694232

   1-Methyl-2-[5-(1-methylbenzimidazol-2-yl)thiophen-2-yl]benzimidazole

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: 344.44

Molecular Weight (Monoisotopic): 344.1096

AlogP: 4.86

#Rotatable Bonds: 2

Polar Surface Area: 35.64

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.42

CX LogP: 4.82

CX LogD: 4.82

Aromatic Rings: 5

Heavy Atoms: 25

QED Weighted: 0.46

Np Likeness Score: -0.68

References

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

Source

Source(1):

• BindingDB Database