5-Chloro-N-(2-chloro-4-((4-methoxybenzyl)amino)phenyl)-2-hydroxybenzamide

ID: ALA4756355

PubChem CID: 162655688

Max Phase: Preclinical

Molecular Formula: C21H18Cl2N2O3

Molecular Weight: 417.29

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(CNc2ccc(NC(=O)c3cc(Cl)ccc3O)c(Cl)c2)cc1

Standard InChI:  InChI=1S/C21H18Cl2N2O3/c1-28-16-6-2-13(3-7-16)12-24-15-5-8-19(18(23)11-15)25-21(27)17-10-14(22)4-9-20(17)26/h2-11,24,26H,12H2,1H3,(H,25,27)

Standard InChI Key:  KCNPLSBWTFOPNG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    8.7240   -7.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0217   -8.2656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3060   -7.8645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6036   -8.2804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6128   -9.0975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3243   -9.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0308   -9.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7149   -7.0326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4356   -8.2509    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3010   -7.0473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3334  -10.3158    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.1380   -7.8350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8495   -8.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5560   -7.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5469   -7.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8312   -6.6019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1288   -7.0178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8587   -9.0533    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.2493   -6.5830    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9608   -6.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6632   -6.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3747   -6.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0771   -6.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0721   -5.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3564   -5.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6540   -5.7512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7836   -5.3229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7776   -4.4979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  2  7  2  0
  1  8  2  0
  1  9  1  0
  3 10  1  0
  6 11  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 12 17  2  0
 13 18  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 21 26  2  0
 19 20  1  0
 15 19  1  0
  9 12  1  0
 24 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4756355

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 417.29

Molecular Weight (Monoisotopic): 416.0694

AlogP: 5.57

#Rotatable Bonds: 6

Polar Surface Area: 70.59

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.39

CX Basic pKa: 3.45

CX LogP: 5.01

CX LogD: 4.71

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.49

Np Likeness Score: -1.42

References

1. Xu J,Berastegui-Cabrera J,Ye N,Carretero-Ledesma M,Pachón-Díaz J,Chen H,Pachón-Ibáñez ME,Sánchez-Céspedes J,Zhou J.  (2020)  Discovery of Novel Substituted N-(4-Amino-2-chlorophenyl)-5-chloro-2-hydroxybenzamide Analogues as Potent Human Adenovirus Inhibitors.,  63  (21): [PMID:33112138] [10.1021/acs.jmedchem.0c01226]

Source

Source(1):

• Scientific Literature