US8703811, 89

ID: ALA3694238

PubChem CID: 58284812

Max Phase: Preclinical

Molecular Formula: C17H19N3OS

Molecular Weight: 313.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC/C(=N\OC)c1ccc(-n2cnc3ccccc32)s1

Standard InChI:  InChI=1S/C17H19N3OS/c1-3-4-7-14(19-21-2)16-10-11-17(22-16)20-12-18-13-8-5-6-9-15(13)20/h5-6,8-12H,3-4,7H2,1-2H3/b19-14+

Standard InChI Key:  ZXDJHCBHUPCLQE-XMHGGMMESA-N

Molfile:  

     RDKit          2D

 22 24  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 C   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
   -4.9327   -6.6841    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4213   -6.8754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8846   -7.9824    0.0000 C   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
    2.4133   -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
  6  7  1  0
  7  8  1  0
  5  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13  9  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 14  1  0
 22 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3694238

   (E)-1-[5-(benzimidazol-1-yl)thiophen-2-yl]-N-methoxypentan-1-imine

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: 313.43

Molecular Weight (Monoisotopic): 313.1249

AlogP: 4.63

#Rotatable Bonds: 6

Polar Surface Area: 39.41

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.77

CX LogP: 4.75

CX LogD: 4.75

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.49

Np Likeness Score: -1.13

References

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

Source

Source(1):

• BindingDB Database