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

ID: ALA4753223

PubChem CID: 135391734

Max Phase: Preclinical

Molecular Formula: C18H11ClN4O3S

Molecular Weight: 398.83

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccccc1Cl)c1ccc2[nH]c(-c3ccc([N+](=O)[O-])s3)nc2c1

Standard InChI:  InChI=1S/C18H11ClN4O3S/c19-11-3-1-2-4-12(11)22-18(24)10-5-6-13-14(9-10)21-17(20-13)15-7-8-16(27-15)23(25)26/h1-9H,(H,20,21)(H,22,24)

Standard InChI Key:  BJBGYQJJEIOBGB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   34.5642  -14.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5631  -15.0251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2778  -15.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2759  -13.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9912  -14.1942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9960  -15.0205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7835  -15.2713    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.2653  -14.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7756  -13.9343    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.0913  -14.5941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5801  -15.2586    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   39.3631  -14.9990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3583  -14.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5722  -13.9239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0365  -15.4821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.7881  -15.1422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.9551  -16.3030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.8483  -15.4369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1343  -15.0240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.8477  -16.2618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.4196  -15.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7064  -15.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9921  -15.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9910  -16.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7101  -16.6704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4213  -16.2569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7083  -14.1958    0.0000 Cl  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
M  CHG  2  15   1  17  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4753223

   ---

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: 398.83

Molecular Weight (Monoisotopic): 398.0240

AlogP: 5.11

#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: 9.77

CX Basic pKa: 3.29

CX LogP: 4.86

CX LogD: 4.86

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.37

Np Likeness Score: -2.15

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