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

ID: ALA4083002

PubChem CID: 137647228

Max Phase: Preclinical

Molecular Formula: C24H17N5O5

Molecular Weight: 455.43

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C24H17N5O5/c1-14-21(29(32)33)23(28(27-14)17-5-3-2-4-6-17)34-18-10-7-15(8-11-18)22-25-19-12-9-16(24(30)31)13-20(19)26-22/h2-13H,1H3,(H,25,26)(H,30,31)

Standard InChI Key:  QURHGCLYZXQURU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
   26.9122  -10.2726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9111  -11.0922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6191  -11.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6174   -9.8638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3260  -10.2690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3308  -11.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1108  -11.3361    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.5882  -10.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1030  -10.0116    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.4034  -10.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8155  -11.3726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6319  -11.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0372  -10.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6200   -9.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8050   -9.9578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8543  -10.6516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.2578   -9.9409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   34.2330   -9.0464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.5223   -8.6429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9191   -9.1941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6211  -10.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3718  -11.2252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9232  -11.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7219  -11.6505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9663  -10.8662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4132  -10.2675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1152   -9.0276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.5727   -9.6388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8571   -8.2523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.4309   -7.8308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2044   -9.8642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2042   -9.0470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4968  -10.2730    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
  1 32  1  0
 32 33  2  0
 32 34  1  0
M  CHG  2  28   1  30  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4083002

   ---

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: 455.43

Molecular Weight (Monoisotopic): 455.1230

AlogP: 5.12

#Rotatable Bonds: 6

Polar Surface Area: 136.17

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.16

CX Basic pKa: 5.47

CX LogP: 3.22

CX LogD: 1.53

Aromatic Rings: 5

Heavy Atoms: 34

QED Weighted: 0.27

Np Likeness Score: -1.36

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