3-{[(5-Chloro-8-hydroxyquinolin-7-yl)methyl]amino}-N-phenylpropanamide

ID: ALA4483313

PubChem CID: 155540729

Max Phase: Preclinical

Molecular Formula: C19H18ClN3O2

Molecular Weight: 355.82

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(CCNCc1cc(Cl)c2cccnc2c1O)Nc1ccccc1

Standard InChI:  InChI=1S/C19H18ClN3O2/c20-16-11-13(19(25)18-15(16)7-4-9-22-18)12-21-10-8-17(24)23-14-5-2-1-3-6-14/h1-7,9,11,21,25H,8,10,12H2,(H,23,24)

Standard InChI Key:  QNRGVIJIAIVIHJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   17.2917   -2.6992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2905   -3.5187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9986   -3.9277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9968   -2.2903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7054   -2.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7062   -3.5146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4147   -3.9216    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1230   -3.5108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1182   -2.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4091   -2.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0005   -4.7449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9943   -1.4731    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.5825   -3.9267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8751   -3.5176    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1671   -3.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4597   -3.5165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7517   -3.9245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0443   -3.5153    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7510   -4.7417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0449   -2.6982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7520   -2.2924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7530   -1.4760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0450   -1.0660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3347   -1.4784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3372   -2.2935    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
 17 18  1  0
 17 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4483313

   ---

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: 355.82

Molecular Weight (Monoisotopic): 355.1088

AlogP: 3.71

#Rotatable Bonds: 6

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: 7.12

CX Basic pKa: 9.59

CX LogP: 2.07

CX LogD: 1.95

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.59

Np Likeness Score: -1.28

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