(E)-5-((6-bromo-2-hydroxy-3-methoxybenzylidene)amino)-1H-benzo[d]imidazol-2(3H)-one

ID: ALA3335242

PubChem CID: 136044167

Max Phase: Preclinical

Molecular Formula: C15H12BrN3O3

Molecular Weight: 362.18

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(Br)c(/C=N/c2ccc3[nH]c(=O)[nH]c3c2)c1O

Standard InChI:  InChI=1S/C15H12BrN3O3/c1-22-13-5-3-10(16)9(14(13)20)7-17-8-2-4-11-12(6-8)19-15(21)18-11/h2-7,20H,1H3,(H2,18,19,21)/b17-7+

Standard InChI Key:  LUTIFBBSUONQTK-REZTVBANSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   18.2987   -1.8696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2976   -2.6891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0056   -3.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7153   -2.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7124   -1.8660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0038   -1.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4186   -1.4547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1279   -1.8607    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8340   -1.4494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5417   -1.8587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5305   -0.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8277   -0.6373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2447   -0.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2468   -1.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0225   -1.6950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4999   -1.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0192   -0.3764    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.3171   -1.0323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0014   -0.6435    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   20.4236   -3.0961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0054   -3.9153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2976   -4.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 14  1  0
 13 11  1  0
 11 12  2  0
 12  9  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
 16 18  2  0
  6 19  1  0
  4 20  1  0
  3 21  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3335242

   ---

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: 362.18

Molecular Weight (Monoisotopic): 361.0062

AlogP: 3.08

#Rotatable Bonds: 3

Polar Surface Area: 90.47

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.76

CX Basic pKa: 0.93

CX LogP: 3.33

CX LogD: 3.31

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.63

Np Likeness Score: -0.72

References

1. Shim HJ, Yang HR, Kim HIe, Kang SA, No KT, Jung YH, Lee ST..  (2014)  Discovery of (E)-5-(benzylideneamino)-1H-benzo[d]imidazol-2(3H)-one derivatives as inhibitors for PTK6.,  24  (19): [PMID:25205190] [10.1016/j.bmcl.2014.08.036]

Source

Source(1):

• Scientific Literature