US8703811, 90

ID: ALA3694239

PubChem CID: 68317968

Max Phase: Preclinical

Molecular Formula: C17H15N3O3S

Molecular Weight: 341.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc2cc3c(cc2n1-c1ccc(C(=O)NC2CC2)s1)OCO3

Standard InChI:  InChI=1S/C17H15N3O3S/c1-9-18-11-6-13-14(23-8-22-13)7-12(11)20(9)16-5-4-15(24-16)17(21)19-10-2-3-10/h4-7,10H,2-3,8H2,1H3,(H,19,21)

Standard InChI Key:  JNZYEACJHJLZHW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 28  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
   -0.3115    2.9665    0.0000 O   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 O   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
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10  6  2  0
 10 11  1  0
 11 12  2  0
 12  4  1  0
 12 13  1  0
 13  2  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 14  1  0
 17 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3694239

   N-cyclopropyl-5-(6-methyl-[1,3]dioxolo[4,5-f]benzimidazol-7-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: 341.39

Molecular Weight (Monoisotopic): 341.0834

AlogP: 3.02

#Rotatable Bonds: 3

Polar Surface Area: 65.38

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.00

CX LogP: 2.51

CX LogD: 2.49

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.80

Np Likeness Score: -1.40

References

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

Source

Source(1):

• BindingDB Database