5-Chloro-N-(4-(cyclopentylamino)-2-fluorophenyl)-2-hydroxybenzamide

ID: ALA4765085

PubChem CID: 162662220

Max Phase: Preclinical

Molecular Formula: C18H18ClFN2O2

Molecular Weight: 348.81

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(NC2CCCC2)cc1F)c1cc(Cl)ccc1O

Standard InChI:  InChI=1S/C18H18ClFN2O2/c19-11-5-8-17(23)14(9-11)18(24)22-16-7-6-13(10-15(16)20)21-12-3-1-2-4-12/h5-10,12,21,23H,1-4H2,(H,22,24)

Standard InChI Key:  UKVQKOLCLPJBCU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   10.8961   -9.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1912  -10.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4821   -9.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7730  -10.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7730  -10.8785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4821  -11.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1912  -10.8785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8961   -8.8355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6052  -10.0613    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4821   -8.8355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3143   -9.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0193  -10.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7284   -9.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7284   -8.8355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0193   -8.4269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3143   -8.8355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4375   -8.4269    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1424   -8.8355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2306   -9.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0290   -9.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4376   -9.1117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8897   -8.5053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4821  -12.1043    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.0193  -10.8863    0.0000 F   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
 19 20  1  0
 20 21  1  0
 21 22  1  0
 18 22  1  0
 17 18  1  0
 14 17  1  0
  9 11  1  0
  6 23  1  0
 12 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4765085

   ---

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: 348.81

Molecular Weight (Monoisotopic): 348.1041

AlogP: 4.79

#Rotatable Bonds: 4

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: 4.33

CX LogP: 4.34

CX LogD: 4.03

Aromatic Rings: 2

Heavy Atoms: 24

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]

Source

Source(1):

• Scientific Literature