N-(2,4-dimethoxyphenyl)-2-(5-nitrofuran-2-yl)-1H-benzo[d]imidazole-5-carboxamide

ID: ALA4753662

PubChem CID: 162653981

Max Phase: Preclinical

Molecular Formula: C20H16N4O6

Molecular Weight: 408.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(NC(=O)c2ccc3[nH]c(-c4ccc([N+](=O)[O-])o4)nc3c2)c(OC)c1

Standard InChI:  InChI=1S/C20H16N4O6/c1-28-12-4-6-14(17(10-12)29-2)23-20(25)11-3-5-13-15(9-11)22-19(21-13)16-7-8-18(30-16)24(26)27/h3-10H,1-2H3,(H,21,22)(H,23,25)

Standard InChI Key:  QPHACVMFZUZEIP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    6.9646   -8.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9635   -9.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6782  -10.1435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6764   -8.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3917   -8.8997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3965   -9.7261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1840   -9.9768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6658   -9.3055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1761   -8.6398    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4920   -9.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9808   -9.9641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7638   -9.7046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7590   -8.8796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9729   -8.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4372  -10.1877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1889   -9.8477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3559  -11.0086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2487  -10.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5346   -9.7295    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2481  -10.9674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8199  -10.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1066   -9.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3923  -10.1374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3912  -10.9632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1103  -11.3761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8216  -10.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6771  -11.3761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9624  -10.9639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1085   -8.9013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8239   -8.4905    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
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  9  5  1  0
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 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
 24 27  1  0
 27 28  1  0
 22 29  1  0
 29 30  1  0
M  CHG  2  15   1  17  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4753662

   ---

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: 408.37

Molecular Weight (Monoisotopic): 408.1070

AlogP: 4.00

#Rotatable Bonds: 6

Polar Surface Area: 132.52

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.15

CX Basic pKa: 2.72

CX LogP: 3.15

CX LogD: 3.14

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.36

Np Likeness Score: -1.63

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