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

ID: ALA4753923

PubChem CID: 135391756

Max Phase: Preclinical

Molecular Formula: C20H16N4O4

Molecular Weight: 376.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccc(C)c(NC(=O)c2ccc3[nH]c(-c4ccc([N+](=O)[O-])o4)nc3c2)c1

Standard InChI:  InChI=1S/C20H16N4O4/c1-11-3-4-12(2)15(9-11)23-20(25)13-5-6-14-16(10-13)22-19(21-14)17-7-8-18(28-17)24(26)27/h3-10H,1-2H3,(H,21,22)(H,23,25)

Standard InChI Key:  WCVFFWJKGHCPTF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   19.0483   -2.3999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0471   -3.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7620   -3.6401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7602   -1.9872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4755   -2.3962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4804   -3.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2678   -3.4735    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7498   -2.8021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2600   -2.1364    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5759   -2.7962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0648   -3.4608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8479   -3.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8429   -2.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0569   -2.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5214   -3.6844    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.2731   -3.3444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4400   -4.5054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3324   -3.6392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6182   -3.2262    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3317   -4.4642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9035   -3.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1900   -3.2229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4758   -3.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4747   -4.4600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1938   -4.8729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9052   -4.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1920   -2.3979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1961   -5.6979    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
 22 27  1  0
 25 28  1  0
M  CHG  2  15   1  17  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4753923

   ---

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: 376.37

Molecular Weight (Monoisotopic): 376.1172

AlogP: 4.60

#Rotatable Bonds: 4

Polar Surface Area: 114.06

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.15

CX Basic pKa: 2.72

CX LogP: 4.49

CX LogD: 4.49

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.40

Np Likeness Score: -1.95

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