US8703811, 98

ID: ALA3694247

PubChem CID: 58284838

Max Phase: Preclinical

Molecular Formula: C22H19N3OS

Molecular Weight: 373.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc2ccc(-c3ccccc3)cc2n1-c1ccc(C(=O)NC2CC2)s1

Standard InChI:  InChI=1S/C22H19N3OS/c1-14-23-18-10-7-16(15-5-3-2-4-6-15)13-19(18)25(14)21-12-11-20(27-21)22(26)24-17-8-9-17/h2-7,10-13,17H,8-9H2,1H3,(H,24,26)

Standard InChI Key:  YYMRCRSHWQIADO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 31  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
   -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
   -2.5987    1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6012    3.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9015    3.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1993    2.9963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1969    1.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8967    0.7484    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  4  1  0
  9 10  1  0
 10  2  1  0
 10 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
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 19  1  0
  7 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3694247

   N-cyclopropyl-5-(2-methyl-6-phenylbenzimidazol-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: 373.48

Molecular Weight (Monoisotopic): 373.1249

AlogP: 4.95

#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: 5.33

CX LogP: 4.53

CX LogD: 4.53

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.55

Np Likeness Score: -1.46

References

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

Source

Source(1):

• BindingDB Database