2-[4-(Hydroxy-phenyl-methyl)-phenyl]-1H-benzoimidazole-5-carboxylic acid amide

ID: ALA3982891

PubChem CID: 11371309

Max Phase: Preclinical

Molecular Formula: C21H17N3O2

Molecular Weight: 343.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1ccc2[nH]c(-c3ccc(C(O)c4ccccc4)cc3)nc2c1

Standard InChI:  InChI=1S/C21H17N3O2/c22-20(26)16-10-11-17-18(12-16)24-21(23-17)15-8-6-14(7-9-15)19(25)13-4-2-1-3-5-13/h1-12,19,25H,(H2,22,26)(H,23,24)

Standard InChI Key:  PKXDIOFCHGEDMH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   27.2578  -23.0209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3157  -22.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3146  -23.4615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0226  -23.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0208  -22.2331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7295  -22.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7342  -23.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5143  -23.7054    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.9916  -23.0403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5065  -22.3809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.8068  -23.0350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2190  -23.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0354  -23.7374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4406  -23.0268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0235  -22.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2084  -22.3271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6079  -22.2335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6077  -21.4163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9003  -22.6423    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.6715  -23.7256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2640  -24.4326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6770  -25.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4830  -23.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6613  -22.3102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.8984  -24.4157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4961  -25.1310    0.0000 C   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  1  0
 21 22  2  0
 22 26  1  0
 25 23  1  0
 23 20  2  0
  1 24  1  0
 25 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3982891

   2-[4-(Hydroxy-phenyl-methyl)-phenyl]-1H-benzoimidazole-5-carboxylic acid amide

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: 343.39

Molecular Weight (Monoisotopic): 343.1321

AlogP: 3.41

#Rotatable Bonds: 4

Polar Surface Area: 92.00

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.03

CX Basic pKa: 4.35

CX LogP: 3.15

CX LogD: 3.15

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.53

Np Likeness Score: -0.81

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