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

ID: ALA3335244

PubChem CID: 4600415

Max Phase: Preclinical

Molecular Formula: C15H11Br2N3O3

Molecular Weight: 441.08

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(Br)c(Br)c(/C=N/c2ccc3[nH]c(=O)[nH]c3c2)c1O

Standard InChI:  InChI=1S/C15H11Br2N3O3/c1-23-12-5-9(16)13(17)8(14(12)21)6-18-7-2-3-10-11(4-7)20-15(22)19-10/h2-6,21H,1H3,(H2,19,20,22)/b18-6+

Standard InChI Key:  IFGPRLKBEQJZAK-NGYBGAFCSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    8.8432   -2.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8421   -2.9203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5501   -3.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2598   -2.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2570   -2.0971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5483   -1.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9631   -1.6859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6724   -2.0918    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3785   -1.6805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0862   -2.0899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0750   -0.4555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3723   -0.8684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7892   -0.8612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7913   -1.6762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5670   -1.9261    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0444   -1.2655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5637   -0.6075    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8616   -1.2635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9681   -3.3273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5499   -4.1464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8421   -4.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1354   -1.6923    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    9.5459   -0.8747    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
  1 22  1  0
  6 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3335244

   5-[(2,3-Dibromo-6-hydroxy-5-methoxyphenyl)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: 441.08

Molecular Weight (Monoisotopic): 438.9167

AlogP: 3.85

#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: 8.32

CX Basic pKa: 0.70

CX LogP: 4.10

CX LogD: 4.05

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.54

Np Likeness Score: -0.65

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