2-(4-(3-methyl-4-nitro-1-phenyl-1H-pyrazol-5-yloxy)phenyl)-5-nitro-1H-benzo[d]imidazole

ID: ALA4076911

PubChem CID: 137650479

Max Phase: Preclinical

Molecular Formula: C23H16N6O5

Molecular Weight: 456.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nn(-c2ccccc2)c(Oc2ccc(-c3nc4cc([N+](=O)[O-])ccc4[nH]3)cc2)c1[N+](=O)[O-]

Standard InChI:  InChI=1S/C23H16N6O5/c1-14-21(29(32)33)23(27(26-14)16-5-3-2-4-6-16)34-18-10-7-15(8-11-18)22-24-19-12-9-17(28(30)31)13-20(19)25-22/h2-13H,1H3,(H,24,25)

Standard InChI Key:  CQFZJNWGLMMMCF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
    2.6152  -10.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6141  -11.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3221  -11.4351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3204   -9.7977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0290  -10.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0338  -11.0216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8138  -11.2701    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2912  -10.6049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8061   -9.9455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1064  -10.5996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5185  -11.3065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3349  -11.3021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7402  -10.5914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3230   -9.8838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5080   -9.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5573  -10.5855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.9360   -8.9803    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    8.6221   -9.1281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3241  -10.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0748  -11.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6262  -11.7612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4249  -11.5844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6693  -10.8002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1162  -10.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8182   -8.9616    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2757   -9.5728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5601   -8.1863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1340   -7.7648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9067   -9.7984    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1991  -10.2072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9065   -8.9812    0.0000 O   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  1  0
  8  9  2  0
  9  5  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  8 10  1  0
 13 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 17  2  0
 18 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 28 29  2  0
 28 30  1  0
 21 28  1  0
 20 31  1  0
 32 33  2  0
 32 34  1  0
  1 32  1  0
M  CHG  4  28   1  30  -1  32   1  34  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4076911

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 456.42

Molecular Weight (Monoisotopic): 456.1182

AlogP: 5.33

#Rotatable Bonds: 6

Polar Surface Area: 142.01

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.90

CX Basic pKa: 3.32

CX LogP: 4.97

CX LogD: 4.97

Aromatic Rings: 5

Heavy Atoms: 34

QED Weighted: 0.27

Np Likeness Score: -1.51

References

1. Galal SA, Abdelsamie AS, Shouman SA, Attia YM, Ali HI, Tabll A, El-Shenawy R, El Abd YS, Ali MM, Mahmoud AE, Abdel-Halim AH, Fyiad AA, Girgis AS, El-Diwani HI..  (2017)  Part I: Design, synthesis and biological evaluation of novel pyrazole-benzimidazole conjugates as checkpoint kinase 2 (Chk2) inhibitors with studying their activities alone and in combination with genotoxic drugs.,  134  [PMID:28433679] [10.1016/j.ejmech.2017.03.090]

Source

Source(1):

• Scientific Literature