N-(4-(((5-Bromothiophen-2-yl)methyl)amino)-2-chlorophenyl)-5-chloro-2-hydroxybenzamide

ID: ALA4757217

PubChem CID: 162657056

Max Phase: Preclinical

Molecular Formula: C18H13BrCl2N2O2S

Molecular Weight: 472.19

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(NCc2ccc(Br)s2)cc1Cl)c1cc(Cl)ccc1O

Standard InChI:  InChI=1S/C18H13BrCl2N2O2S/c19-17-6-3-12(26-17)9-22-11-2-4-15(14(21)8-11)23-18(25)13-7-10(20)1-5-16(13)24/h1-8,22,24H,9H2,(H,23,25)

Standard InChI Key:  FRNFXFUGYIUNDA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    9.8610   -8.2623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1556   -8.6772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4470   -8.2709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7416   -8.6858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7449   -9.5030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4535   -9.9052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1589   -9.4944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8578   -7.4451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5738   -8.6686    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4438   -7.4537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4608  -10.7224    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.2792   -8.2536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9878   -8.6600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6932   -8.2450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6858   -7.4279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9772   -7.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2718   -7.4365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9910   -9.4771    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.3912   -7.0170    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1040   -7.4192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8094   -7.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5555   -7.3361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0979   -6.7247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6870   -6.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8902   -6.1931    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.0147   -5.2732    0.0000 Br  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
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 21 25  1  0
 24 26  1  0
 20 21  1  0
 19 20  1  0
 15 19  1  0
  9 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4757217

   ---

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: 472.19

Molecular Weight (Monoisotopic): 469.9258

AlogP: 6.39

#Rotatable Bonds: 5

Polar Surface Area: 61.36

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.39

CX Basic pKa: 3.12

CX LogP: 6.01

CX LogD: 5.71

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.40

Np Likeness Score: -2.10

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