2-(5-nitrothiophen-2-yl)-N-(3,4,5-trimethoxyphenyl)-1H-benzo[d]imidazole-5-carboxamide

ID: ALA4799838

PubChem CID: 135391927

Max Phase: Preclinical

Molecular Formula: C21H18N4O6S

Molecular Weight: 454.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(NC(=O)c2ccc3[nH]c(-c4ccc([N+](=O)[O-])s4)nc3c2)cc(OC)c1OC

Standard InChI:  InChI=1S/C21H18N4O6S/c1-29-15-9-12(10-16(30-2)19(15)31-3)22-21(26)11-4-5-13-14(8-11)24-20(23-13)17-6-7-18(32-17)25(27)28/h4-10H,1-3H3,(H,22,26)(H,23,24)

Standard InChI Key:  MGMGWWPXIPRLCS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    6.6401   -2.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6389   -3.4480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3537   -3.8609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3519   -2.2079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0672   -2.6171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0721   -3.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8595   -3.6944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3415   -3.0228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8517   -2.3571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1676   -3.0171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6565   -3.6815    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.4396   -3.4220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.6486   -2.3468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1130   -3.9053    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8647   -3.5652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0317   -4.7262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9241   -3.8600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2100   -3.4469    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9235   -4.6850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4952   -3.8588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7819   -3.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0676   -3.8549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0664   -4.6807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7856   -5.0936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4969   -4.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3522   -5.0936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6376   -4.6815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7878   -5.9186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0745   -6.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3536   -3.4415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3547   -2.6165    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
 24 27  1  0
 27 28  1  0
 25 29  1  0
 29 30  1  0
 23 31  1  0
 31 32  1  0
M  CHG  2  15   1  17  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4799838

   ---

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: 454.46

Molecular Weight (Monoisotopic): 454.0947

AlogP: 4.48

#Rotatable Bonds: 7

Polar Surface Area: 128.61

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.78

CX Basic pKa: 3.29

CX LogP: 3.79

CX LogD: 3.78

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.31

Np Likeness Score: -1.48

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