2-{4-[(3-Bromo-4,5-dimethoxy-phenyl)-hydroxy-methyl]-phenyl}-1H-benzoimidazole-5-carboxylic acid amide

ID: ALA3985771

PubChem CID: 11352125

Max Phase: Preclinical

Molecular Formula: C23H20BrN3O4

Molecular Weight: 482.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C(O)c2ccc(-c3nc4cc(C(N)=O)ccc4[nH]3)cc2)cc(Br)c1OC

Standard InChI:  InChI=1S/C23H20BrN3O4/c1-30-19-11-15(9-16(24)21(19)31-2)20(28)12-3-5-13(6-4-12)23-26-17-8-7-14(22(25)29)10-18(17)27-23/h3-11,20,28H,1-2H3,(H2,25,29)(H,26,27)

Standard InChI Key:  BLXMMBJSCDOVAB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    8.1075   -2.3517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1654   -1.9728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1642   -2.7923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8723   -3.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705   -1.5639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5791   -1.9692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5839   -2.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3639   -3.0362    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8413   -2.3711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3562   -1.7117    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6565   -2.3658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0687   -3.0727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8851   -3.0683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2903   -2.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8731   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0581   -1.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4576   -1.5644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4574   -0.7472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -1.9731    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5212   -3.0564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1137   -3.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5267   -4.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3447   -4.4622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7480   -3.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3327   -3.0452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5110   -1.6411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5652   -3.7378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9813   -4.4411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7594   -5.1664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3568   -5.8776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1229   -5.1781    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10  6  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  9 11  1  0
  2 17  1  0
 17 18  2  0
 17 19  1  0
 14  1  1  0
  1 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
  1 26  1  0
 24 27  1  0
 27 28  1  0
 23 29  1  0
 29 30  1  0
 22 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3985771

   2-[4-[(3-bromo-4,5-dimethoxyphenyl)-hydroxymethyl]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: 482.33

Molecular Weight (Monoisotopic): 481.0637

AlogP: 4.19

#Rotatable Bonds: 6

Polar Surface Area: 110.46

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.03

CX Basic pKa: 4.35

CX LogP: 3.61

CX LogD: 3.60

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.38

Np Likeness Score: -0.48

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