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

ID: ALA4753799

PubChem CID: 135391762

Max Phase: Preclinical

Molecular Formula: C20H16N4O3S

Molecular Weight: 392.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccc(C)c(NC(=O)c2ccc3[nH]c(-c4ccc([N+](=O)[O-])s4)nc3c2)c1

Standard InChI:  InChI=1S/C20H16N4O3S/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:  BARZUAPTZZGEIG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   19.5067   -2.0790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5054   -2.9065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2203   -3.3194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2185   -1.6663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9338   -2.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9387   -2.9019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7261   -3.1527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.2081   -2.4813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7184   -1.8156    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.0342   -2.4754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5231   -3.1400    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.3062   -2.8804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3013   -2.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5152   -1.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9797   -3.3636    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.7314   -3.0236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8983   -4.1845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7907   -3.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0765   -2.9054    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7900   -4.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3618   -3.3173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6483   -2.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9341   -3.3132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9330   -4.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6522   -4.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3635   -4.1384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6504   -2.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6544   -5.3770    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:

   

   ALA4753799

   ---

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: -2.11

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