2-[4-(4-chloro-phenoxy)-phenyl]-1H-benzoimidazole-5-carboxylic acid methylamide

ID: ALA3982809

PubChem CID: 10110159

Max Phase: Preclinical

Molecular Formula: C21H16ClN3O2

Molecular Weight: 377.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)c1ccc2[nH]c(-c3ccc(Oc4ccc(Cl)cc4)cc3)nc2c1

Standard InChI:  InChI=1S/C21H16ClN3O2/c1-23-21(26)14-4-11-18-19(12-14)25-20(24-18)13-2-7-16(8-3-13)27-17-9-5-15(22)6-10-17/h2-12H,1H3,(H,23,26)(H,24,25)

Standard InChI Key:  SPMJCKLIOKTQLW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   10.8421   -7.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5927   -7.7682    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1437   -7.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7309   -6.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9275   -6.6148    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9650   -7.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3736   -6.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9650   -5.7331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1437   -5.7331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1949   -6.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6076   -7.1567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6076   -5.7331    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1949   -5.0212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1302   -7.8444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1302   -8.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4184   -9.0743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7065   -8.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7065   -7.8444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4184   -7.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9988   -9.0743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2870   -8.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5752   -9.0743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8633   -8.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8633   -7.8444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5752   -7.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2870   -7.8444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1515   -7.4316    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  1  5  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  4  9  2  0
  3  6  2  0
 10 11  2  0
 12 13  1  0
 10 12  1  0
  7 10  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 14 19  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 21 26  2  0
 20 21  1  0
 24 27  1  0
 17 20  1  0
  1 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3982809

   2-[4-(4-chlorophenoxy)phenyl]-N-methyl-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: 377.83

Molecular Weight (Monoisotopic): 377.0931

AlogP: 5.04

#Rotatable Bonds: 4

Polar Surface Area: 67.01

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.07

CX Basic pKa: 4.39

CX LogP: 4.46

CX LogD: 4.46

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.52

Np Likeness Score: -1.28

References

1.  (2007)  2-phenyl benzimidazoles and imidazo-4,5|-pyridines as CDS1/CHK2-inhibitors and adjuvants to chemotherapy or radiation therapy in the treatment of cancer, 

Source

Source(1):

• Patent Bioactivity Data