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

ID: ALA4791057

PubChem CID: 162672094

Max Phase: Preclinical

Molecular Formula: C19H20Cl2N2O2

Molecular Weight: 379.29

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(NCC2CCCC2)cc1Cl)c1cc(Cl)ccc1O

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

Standard InChI Key:  UONOIMILWQNVBH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    7.6455   -5.9135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9364   -6.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2274   -5.9135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5224   -6.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5224   -7.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2274   -7.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9364   -7.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6455   -5.0963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3505   -6.3221    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2274   -5.0963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0596   -5.9135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7687   -6.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4736   -5.9135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4736   -5.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7687   -4.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0596   -5.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1827   -4.6877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8918   -5.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8918   -5.9135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7687   -7.1392    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.2274   -8.3650    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.2313   -6.3922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4838   -7.1694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3011   -7.1694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5535   -6.3922    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
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 11 16  2  0
 18 19  1  0
 17 18  1  0
 14 17  1  0
 12 20  1  0
  9 11  1  0
  6 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4791057

   ---

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: 5.55

#Rotatable Bonds: 5

Polar Surface Area: 61.36

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.39

CX Basic pKa: 4.72

CX LogP: 5.11

CX LogD: 4.81

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.64

Np Likeness Score: -1.29

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]

2. Xu J, Wu W, Chen H, Xue Y, Bao X, Zhou J..  (2021)  Substituted N-(4-amino-2-chlorophenyl)-5-chloro-2-hydroxybenzamide analogues potently inhibit respiratory syncytial virus (RSV) replication and RSV infection-associated inflammatory responses.,  39  [PMID:33895704] [10.1016/j.bmc.2021.116157]

Source

Source(1):

• Scientific Literature