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

ID: ALA3335235

PubChem CID: 5240683

Max Phase: Preclinical

Molecular Formula: C16H14BrN3O3

Molecular Weight: 376.21

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H14BrN3O3/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:  IWFRXGXODAQTRT-QGMBQPNBSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   15.9544  -11.6140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9533  -12.4335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6613  -12.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3710  -12.4330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3682  -11.6104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6596  -11.2051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0743  -11.1991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7836  -11.6051    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4898  -11.1938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1974  -11.6031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1862   -9.9687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4835  -10.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9005  -10.3745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9025  -11.1894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6782  -11.4393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1556  -10.7788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6749  -10.1208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9728  -10.7767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0794  -12.8405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6611  -13.6597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9533  -14.0681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9531  -14.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2466  -11.2056    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
M  END

Alternative Forms

1. Parent:

   

   ALA3335235

   5-[(5-Bromo-3-ethoxy-2-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: 376.21

Molecular Weight (Monoisotopic): 375.0219

AlogP: 3.47

#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: 8.90

CX Basic pKa: 1.13

CX LogP: 3.68

CX LogD: 3.67

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.61

Np Likeness Score: -1.17

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