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

ID: ALA4789862

PubChem CID: 135391760

Max Phase: Preclinical

Molecular Formula: C20H16N4O3S

Molecular Weight: 392.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(C)cc(NC(=O)c2ccc3[nH]c(-c4ccc([N+](=O)[O-])s4)nc3c2)c1

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

Standard InChI Key:  VTOPSQLVFRSHMB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   20.0066  -12.7539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0054  -13.5812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7202  -13.9941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7184  -12.3411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4338  -12.7503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4387  -13.5767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2261  -13.8276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.7081  -13.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2183  -12.4904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.5342  -13.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0230  -13.8147    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.8061  -13.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8013  -12.7302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0151  -12.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4797  -14.0385    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.2313  -13.6984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3982  -14.8594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907  -13.9932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5765  -13.5801    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2900  -14.8182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8617  -13.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1484  -13.5768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4341  -13.9881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4330  -14.8139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1521  -15.2268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8635  -14.8132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7202  -13.5747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1544  -16.0518    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
 25 28  1  0
M  CHG  2  15   1  17  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4789862

   ---

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: -1.89

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