2-{[(5-Chloro-8-hydroxyquinolin-7-yl)methyl]amino}-N-phenylacetamide

ID: ALA4558237

PubChem CID: 155557598

Max Phase: Preclinical

Molecular Formula: C18H16ClN3O2

Molecular Weight: 341.80

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(CNCc1cc(Cl)c2cccnc2c1O)Nc1ccccc1

Standard InChI:  InChI=1S/C18H16ClN3O2/c19-15-9-12(18(24)17-14(15)7-4-8-21-17)10-20-11-16(23)22-13-5-2-1-3-6-13/h1-9,20,24H,10-11H2,(H,22,23)

Standard InChI Key:  ZUFWYNDCNPXQNR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    7.5225   -2.5960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5214   -3.4155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2294   -3.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2276   -2.1871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9363   -2.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9370   -3.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6455   -3.8185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3538   -3.4076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3491   -2.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6400   -2.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2313   -4.6417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2252   -1.3699    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.8133   -3.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1060   -3.4144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3979   -3.8224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6905   -3.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9825   -3.8213    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6912   -2.5961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2751   -3.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2808   -2.5970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5742   -2.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8652   -2.5960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8672   -3.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5743   -3.8228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  3 11  1  0
  4 12  1  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4558237

   ---

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: 341.80

Molecular Weight (Monoisotopic): 341.0931

AlogP: 3.32

#Rotatable Bonds: 5

Polar Surface Area: 74.25

Molecular Species: BASE

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.20

CX Basic pKa: 8.64

CX LogP: 2.00

CX LogD: 1.91

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.67

Np Likeness Score: -1.36

References

1. Chen C, Yang X, Fang H, Hou X..  (2019)  Design, synthesis and preliminary bioactivity evaluations of 8-hydroxyquinoline derivatives as matrix metalloproteinase (MMP) inhibitors.,  181  [PMID:31415980] [10.1016/j.ejmech.2019.111563]

Source

Source(1):

• Scientific Literature