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

ID: ALA4100980

PubChem CID: 137658886

Max Phase: Preclinical

Molecular Formula: C25H16N6O5

Molecular Weight: 480.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nn(-c2ccc(C#N)cc2)c(Oc2ccc(-c3nc4cc(C(=O)O)ccc4[nH]3)cc2)c1[N+](=O)[O-]

Standard InChI:  InChI=1S/C25H16N6O5/c1-14-22(31(34)35)24(30(29-14)18-7-2-15(13-26)3-8-18)36-19-9-4-16(5-10-19)23-27-20-11-6-17(25(32)33)12-21(20)28-23/h2-12H,1H3,(H,27,28)(H,32,33)

Standard InChI Key:  UVJAHTQJJBTJDW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 36 40  0  0  0  0  0  0  0  0999 V2000
   37.8040   -9.9590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8029  -10.7785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5109  -11.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5091   -9.5501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2177   -9.9554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2225  -10.7740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0026  -11.0224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.4799  -10.3573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9948   -9.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.2951  -10.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7073  -11.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.5237  -11.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9289  -10.3438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.5118   -9.6362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6967   -9.6441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7461  -10.3379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.1496   -9.6273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.9606   -9.5333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   45.1248   -8.7327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   44.4141   -8.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.8108   -8.8805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.5128  -10.1356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.2635  -10.9115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.8150  -11.5136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.6137  -11.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.8580  -10.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.3049   -9.9539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0069   -8.7140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.4645   -9.3252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.7488   -7.9386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.3227   -7.5171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0962   -9.5505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0960   -8.7333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.3886   -9.9593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   47.1682  -11.9360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.7212  -12.5376    0.0000 N   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
 35 36  3  0
 25 35  1  0
M  CHG  2  28   1  30  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4100980

   ---

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: 480.44

Molecular Weight (Monoisotopic): 480.1182

AlogP: 4.99

#Rotatable Bonds: 6

Polar Surface Area: 159.96

Molecular Species: ACID

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.16

CX Basic pKa: 5.47

CX LogP: 3.08

CX LogD: 1.39

Aromatic Rings: 5

Heavy Atoms: 36

QED Weighted: 0.25

Np Likeness Score: -1.54

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