5-Chloro-N-(2-chloro-4-(cyclopentylamino)benzyl)-2-hydroxybenzamide

ID: ALA4756349

PubChem CID: 156811522

Max Phase: Preclinical

Molecular Formula: C19H20Cl2N2O2

Molecular Weight: 379.29

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(NCc1ccc(NC2CCCC2)cc1Cl)c1cc(Cl)ccc1O

Standard InChI:  InChI=1S/C19H20Cl2N2O2/c20-13-6-8-18(24)16(9-13)19(25)22-11-12-5-7-15(10-17(12)21)23-14-3-1-2-4-14/h5-10,14,23-24H,1-4,11H2,(H,22,25)

Standard InChI Key:  VERBNWDEJMSTPT-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   10.5437   -9.2481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8346   -9.6567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1255   -9.2481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4205   -9.6567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4205  -10.4739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1255  -10.8825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8346  -10.4739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5437   -8.4309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2486   -9.6567    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1255   -8.4309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9577   -9.2481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6668   -9.6567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6668  -10.4739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3718  -10.8825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0809  -10.4739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0809   -9.6567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3718   -9.2481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7899  -10.8825    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4949  -10.4739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2422  -10.8041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7900  -10.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3814   -9.4886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5831   -9.6593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9577  -10.8825    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.1255  -11.6997    0.0000 Cl  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
 11 12  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
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 19 23  1  0
 18 19  1  0
 15 18  1  0
 13 24  1  0
  9 11  1  0
  6 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4756349

   ---

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: 379.29

Molecular Weight (Monoisotopic): 378.0902

AlogP: 4.98

#Rotatable Bonds: 5

Polar Surface Area: 61.36

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.66

CX Basic pKa: 4.49

CX LogP: 5.15

CX LogD: 4.97

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.69

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