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

ID: ALA4786187

PubChem CID: 135391763

Max Phase: Preclinical

Molecular Formula: C19H14N4O4S

Molecular Weight: 394.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cccc(NC(=O)c2ccc3[nH]c(-c4ccc([N+](=O)[O-])s4)nc3c2)c1

Standard InChI:  InChI=1S/C19H14N4O4S/c1-27-13-4-2-3-12(10-13)20-19(24)11-5-6-14-15(9-11)22-18(21-14)16-7-8-17(28-16)23(25)26/h2-10H,1H3,(H,20,24)(H,21,22)

Standard InChI Key:  FOJNIBJGLFPPCK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    7.0811  -14.7942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0799  -15.6214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7947  -16.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7929  -14.3814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5082  -14.7905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5130  -15.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3004  -15.8676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7823  -15.1962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2926  -14.5306    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6083  -15.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0972  -15.8549    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.8802  -15.5953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8753  -14.7703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0893  -14.5202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5536  -16.0785    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3052  -15.7385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4722  -16.8993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3652  -16.0332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6511  -15.6203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3645  -16.8582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9365  -16.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2231  -15.6169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5089  -16.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5078  -16.8539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2269  -17.2668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9382  -16.8532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7950  -15.6147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7961  -14.7898    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
 27 28  1  0
M  CHG  2  15   1  17  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4786187

   ---

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: 394.41

Molecular Weight (Monoisotopic): 394.0736

AlogP: 4.46

#Rotatable Bonds: 5

Polar Surface Area: 110.15

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.78

CX Basic pKa: 3.29

CX LogP: 4.10

CX LogD: 4.10

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.38

Np Likeness Score: -1.97

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