(E)-5-((2,4-dihydroxybenzylidene)amino)-1H-benzo[d]imidazol-2(3H)-one

ID: ALA3335239

PubChem CID: 683690

Max Phase: Preclinical

Molecular Formula: C14H11N3O3

Molecular Weight: 269.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]c2ccc(/N=C/c3ccc(O)cc3O)cc2[nH]1

Standard InChI:  InChI=1S/C14H11N3O3/c18-10-3-1-8(13(19)6-10)7-15-9-2-4-11-12(5-9)17-14(20)16-11/h1-7,18-19H,(H2,16,17,20)/b15-7+

Standard InChI Key:  AOJDVIAMXNDJLT-VIZOYTHASA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   11.5094  -10.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5083  -11.2862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2163  -11.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9260  -11.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9232  -10.4630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2145  -10.0578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6293  -10.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3386  -10.4577    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0447  -10.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7524  -10.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7412   -8.8214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0385   -9.2343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4554   -9.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4575  -10.0420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2332  -10.2920    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7106   -9.6314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2299   -8.9734    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5278   -9.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6343  -11.6932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8002  -11.6942    0.0000 O   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
  2 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3335239

   5-[(2,4-Dihydroxyphenyl)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: 269.26

Molecular Weight (Monoisotopic): 269.0800

AlogP: 2.02

#Rotatable Bonds: 2

Polar Surface Area: 101.47

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.52

CX Basic pKa: 1.74

CX LogP: 2.41

CX LogD: 2.38

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.54

Np Likeness Score: -0.67

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