5-Chloro-N-(2-chloro-4-(propylamino)phenyl)-2-hydroxybenzamide

ID: ALA4757265

PubChem CID: 162656559

Max Phase: Preclinical

Molecular Formula: C16H16Cl2N2O2

Molecular Weight: 339.22

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCNc1ccc(NC(=O)c2cc(Cl)ccc2O)c(Cl)c1

Standard InChI:  InChI=1S/C16H16Cl2N2O2/c1-2-7-19-11-4-5-14(13(18)9-11)20-16(22)12-8-10(17)3-6-15(12)21/h3-6,8-9,19,21H,2,7H2,1H3,(H,20,22)

Standard InChI Key:  LKHHYCQJKRLODE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    9.9705   -6.6424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2601   -7.0486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5523   -6.6376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8460   -7.0439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8433   -7.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5510   -8.2720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2615   -7.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9691   -5.8252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6741   -7.0533    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5551   -5.8205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3846   -6.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0923   -7.0540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7986   -6.6477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8013   -5.8305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0936   -5.4196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3873   -5.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5118   -5.4243    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2154   -5.8353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9258   -5.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0895   -7.8711    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.5483   -9.0892    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.6336   -5.8334    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
M  END

Alternative Forms

1. Parent:

   

   ALA4757265

   ---

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: 339.22

Molecular Weight (Monoisotopic): 338.0589

AlogP: 4.77

#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: 7.39

CX Basic pKa: 4.54

CX LogP: 4.32

CX LogD: 4.02

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.74

Np Likeness Score: -1.67

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