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

ID: ALA3335236

PubChem CID: 4603900

Max Phase: Preclinical

Molecular Formula: C16H15N3O3

Molecular Weight: 297.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOc1cccc(/C=N/c2ccc3[nH]c(=O)[nH]c3c2)c1O

Standard InChI:  InChI=1S/C16H15N3O3/c1-2-22-14-5-3-4-10(15(14)20)9-17-11-6-7-12-13(8-11)19-16(21)18-12/h3-9,20H,2H2,1H3,(H2,18,19,21)/b17-9+

Standard InChI Key:  ZSEAHTRIEMNDGU-RQZCQDPDSA-N

Molfile:  

     RDKit          2D

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   23.7249  -12.6729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4329  -13.0819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1426  -12.6724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1398  -11.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4311  -11.4445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8459  -11.4385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5552  -11.8444    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.2613  -11.4332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9690  -11.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9578  -10.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2551  -10.6210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6720  -10.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6741  -11.4288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4498  -11.6787    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.9272  -11.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4465  -10.3602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.7444  -11.0161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.8509  -13.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4327  -13.8991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7249  -14.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7247  -15.1247    0.0000 C   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
M  END

Alternative Forms

1. Parent:

   

   ALA3335236

   5-[(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: 297.31

Molecular Weight (Monoisotopic): 297.1113

AlogP: 2.71

#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: 9.33

CX Basic pKa: 1.46

CX LogP: 2.92

CX LogD: 2.91

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.65

Np Likeness Score: -1.24

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