2-[4-(2-Methyl-benzylsulfamoyl)-phenyl]-1H-benzoimidazole-5-carboxylic acid amide

ID: ALA3983526

PubChem CID: 11281575

Max Phase: Preclinical

Molecular Formula: C22H20N4O3S

Molecular Weight: 420.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccccc1CNS(=O)(=O)c1ccc(-c2nc3cc(C(N)=O)ccc3[nH]2)cc1

Standard InChI:  InChI=1S/C22H20N4O3S/c1-14-4-2-3-5-17(14)13-24-30(28,29)18-9-6-15(7-10-18)22-25-19-11-8-16(21(23)27)12-20(19)26-22/h2-12,24H,13H2,1H3,(H2,23,27)(H,25,26)

Standard InChI Key:  HSJSRWDTQSEZSV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   19.1462  -24.2681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1503  -25.0853    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.8560  -24.6731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2098  -24.7097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2087  -25.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9167  -25.9382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9150  -24.3008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6236  -24.7061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6284  -25.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4084  -25.7731    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8858  -25.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4006  -24.4486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7010  -25.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1131  -25.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9295  -25.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3348  -25.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9176  -24.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1026  -24.3948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5020  -24.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5018  -23.4841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7944  -24.7100    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5656  -25.7933    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3828  -25.7874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7965  -26.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3924  -27.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8054  -27.9038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6235  -27.8983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0268  -27.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6114  -26.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0114  -25.7688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
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  9 10  1  0
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 11 12  2  0
 12  8  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 11 13  1  0
  4 19  1  0
 19 20  2  0
 19 21  1  0
 16  2  1  0
  2 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3983526

   2-[4-[(2-methylphenyl)methylsulfamoyl]phenyl]-3H-benzimidazole-5-carboxamide

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: 420.49

Molecular Weight (Monoisotopic): 420.1256

AlogP: 3.12

#Rotatable Bonds: 6

Polar Surface Area: 117.94

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.97

CX Basic pKa: 4.26

CX LogP: 3.20

CX LogD: 3.20

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.44

Np Likeness Score: -1.67

References

1.  (2007)  2-phenyl-benzimidazol and 2-phenyl-imidazo-4,5]-pyridine derivatives as checkpoint kinase CDS1 (CHK2) inhibitors for the treatment of cancer, 

Source

Source(1):

• Patent Bioactivity Data