N-(3,4-dimethylphenyl)-2-(5-nitrothiophen-2-yl)-1H-benzo[d]imidazole-5-carboxamide

ID: ALA4796858

PubChem CID: 135391778

Max Phase: Preclinical

Molecular Formula: C20H16N4O3S

Molecular Weight: 392.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccc(NC(=O)c2ccc3[nH]c(-c4ccc([N+](=O)[O-])s4)nc3c2)cc1C

Standard InChI:  InChI=1S/C20H16N4O3S/c1-11-3-5-14(9-12(11)2)21-20(25)13-4-6-15-16(10-13)23-19(22-15)17-7-8-18(28-17)24(26)27/h3-10H,1-2H3,(H,21,25)(H,22,23)

Standard InChI Key:  KGKCNAYNWSNWQX-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   19.3813   -7.2914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3802   -8.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0950   -8.5316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0933   -6.8787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8086   -7.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8135   -8.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6009   -8.3651    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0828   -7.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5931   -7.0279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9089   -7.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3977   -8.3522    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.1808   -8.0927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1760   -7.2677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3899   -7.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8544   -8.5759    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.6060   -8.2359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7729   -9.3969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6655   -8.5307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9513   -8.1176    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6648   -9.3557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2366   -8.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5232   -8.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8089   -8.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8078   -9.3514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5270   -9.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2383   -9.3507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0950   -8.1122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0936   -9.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 10  2  0
  8 10  1  0
 15 16  2  0
 15 17  1  0
 12 15  1  0
  2 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 23 27  1  0
 24 28  1  0
M  CHG  2  15   1  17  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4796858

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 392.44

Molecular Weight (Monoisotopic): 392.0943

AlogP: 5.07

#Rotatable Bonds: 4

Polar Surface Area: 100.92

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.78

CX Basic pKa: 3.29

CX LogP: 5.29

CX LogD: 5.28

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.37

Np Likeness Score: -2.07

References

1. Sharma, Mousmee, Prasher, Parteek.  (2020)  An epigrammatic status of the azole-based antimalarial drugs,  11  (2): [PMID:33479627] [10.1039/c9md00479c]

Source

Source(1):

• Scientific Literature