(E)-5-((2,3-dibromo-5-ethoxy-6-hydroxybenzylidene)amino)-1H-benzo[d]imidazol-2(3H)-one

ID: ALA3335245

PubChem CID: 1128774

Max Phase: Preclinical

Molecular Formula: C16H13Br2N3O3

Molecular Weight: 455.11

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H13Br2N3O3/c1-2-24-13-6-10(17)14(18)9(15(13)22)7-19-8-3-4-11-12(5-8)21-16(23)20-11/h3-7,22H,2H2,1H3,(H2,20,21,23)/b19-7+

Standard InChI Key:  CWDLJPOSYGJLKO-FBCYGCLPSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   16.9367   -2.8643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9356   -3.6838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6436   -4.0928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3533   -3.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3505   -2.8607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6418   -2.4554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0566   -2.4494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7659   -2.8553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.4720   -2.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1797   -2.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1685   -1.2190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4658   -1.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8827   -1.6248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8848   -2.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6605   -2.6896    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.1379   -2.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6572   -1.3711    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.9551   -2.0270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0616   -4.0908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6434   -4.9100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3510   -5.3187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3508   -6.1359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2289   -2.4558    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   17.6394   -1.6382    0.0000 Br  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
  6 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3335245

   5-[(2,3-Dibromo-5-ethoxy-6-hydroxyphenyl)methylideneamino]-1,3-dihydrobenzimidazol-2-one

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: 455.11

Molecular Weight (Monoisotopic): 452.9324

AlogP: 4.24

#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: 8.31

CX Basic pKa: 0.70

CX LogP: 4.45

CX LogD: 4.40

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.51

Np Likeness Score: -0.84

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