5-Chloro-N-(2-chloro-4-((3-hydroxypropyl)amino)phenyl)-2-hydroxybenzamide

ID: ALA4789868

PubChem CID: 162670304

Max Phase: Preclinical

Molecular Formula: C16H16Cl2N2O3

Molecular Weight: 355.22

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H16Cl2N2O3/c17-10-2-5-15(22)12(8-10)16(23)20-14-4-3-11(9-13(14)18)19-6-1-7-21/h2-5,8-9,19,21-22H,1,6-7H2,(H,20,23)

Standard InChI Key:  FPGYGZNDBOWJIY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   11.3540   -6.6325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1107   -7.4529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4016   -7.8615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6926   -7.4529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9876   -7.8615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9876   -8.6787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6926   -9.0873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4017   -8.6787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1107   -6.6357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8198   -7.8615    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6926   -6.6357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5248   -7.4529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2339   -7.8615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9388   -7.4529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9388   -6.6357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2339   -6.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5248   -6.6357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6479   -6.2271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3570   -7.4529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0661   -7.8615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0661   -8.6787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2339   -8.6787    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.6926   -9.9045    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  3  8  2  0
  2  9  2  0
  2 10  1  0
  4 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
  1 19  1  0
 19 20  1  0
 20 21  1  0
 18  1  1  0
 15 18  1  0
 13 22  1  0
 10 12  1  0
  7 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4789868

   ---

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: 355.22

Molecular Weight (Monoisotopic): 354.0538

AlogP: 3.75

#Rotatable Bonds: 6

Polar Surface Area: 81.59

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.39

CX Basic pKa: 4.54

CX LogP: 2.81

CX LogD: 2.51

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.60

Np Likeness Score: -1.43

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