US8703811, 96

ID: ALA3694245

PubChem CID: 58284901

Max Phase: Preclinical

Molecular Formula: C18H16ClN3OS

Molecular Weight: 357.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc(-c2ccc(Cl)cc2)cn1-c1ccc(C(=O)NC2CC2)s1

Standard InChI:  InChI=1S/C18H16ClN3OS/c1-11-20-15(12-2-4-13(19)5-3-12)10-22(11)17-9-8-16(24-17)18(23)21-14-6-7-14/h2-5,8-10,14H,6-7H2,1H3,(H,21,23)

Standard InChI Key:  HVPYHSLAUKYSHL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    6.1467   -1.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9531   -1.9978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9511   -0.8815    0.0000 N   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
    2.7343   -2.9815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2010   -3.2956    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8092   -4.6676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1521   -5.9965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2383   -7.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5578   -6.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2871   -4.8423    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.9103   -6.9623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0043   -8.1586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1475   -6.1127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5022   -6.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9154   -6.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2671   -7.9568    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
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383    1.3500    0.0000 Cl  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  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  2  1  0
  6  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  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 15  1  0
  4 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3694245

   5-[4-(4-chlorophenyl)-2-methylimidazol-1-yl]-N-cyclopropylthiophene-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: 357.87

Molecular Weight (Monoisotopic): 357.0703

AlogP: 4.45

#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: 5.49

CX LogP: 4.12

CX LogD: 4.11

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.75

Np Likeness Score: -1.76

References

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

Source

Source(1):

• BindingDB Database