(E)-5-((5-chloro-3-ethoxy-2-hydroxybenzylidene)amino)-1H-benzo[d]imidazol-2(3H)-one

ID: ALA3335237

PubChem CID: 136044171

Max Phase: Preclinical

Molecular Formula: C16H14ClN3O3

Molecular Weight: 331.76

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOc1cc(Cl)cc(/C=N/c2ccc3[nH]c(=O)[nH]c3c2)c1O

Standard InChI:  InChI=1S/C16H14ClN3O3/c1-2-23-14-6-10(17)5-9(15(14)21)8-18-11-3-4-12-13(7-11)20-16(22)19-12/h3-8,21H,2H2,1H3,(H2,19,20,22)/b18-8+

Standard InChI Key:  OKSAVGBTXALUEE-QGMBQPNBSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    0.9272   -7.3093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9261   -8.1288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6341   -8.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3438   -8.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3409   -7.3057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6323   -6.9004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0471   -6.8944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7563   -7.3004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4625   -6.8891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1702   -7.2984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1590   -5.6640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4562   -6.0769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8732   -6.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8753   -6.8847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6510   -7.1346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1284   -6.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6477   -5.8161    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9456   -6.4720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0521   -8.5358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6339   -9.3550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9261   -9.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9259  -10.5806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2194   -6.9009    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  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
  4 19  1  0
  3 20  1  0
 20 21  1  0
 21 22  1  0
  1 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3335237

   ---

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: 331.76

Molecular Weight (Monoisotopic): 331.0724

AlogP: 3.36

#Rotatable Bonds: 4

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: 8.82

CX Basic pKa: 1.15

CX LogP: 3.52

CX LogD: 3.50

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.64

Np Likeness Score: -1.42

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