3-{[(8-Hydroxyquinolin-5-yl)methyl]amino}-N-phenylpropanamide

ID: ALA4529344

PubChem CID: 155545205

Max Phase: Preclinical

Molecular Formula: C19H19N3O2

Molecular Weight: 321.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(CCNCc1ccc(O)c2ncccc12)Nc1ccccc1

Standard InChI:  InChI=1S/C19H19N3O2/c23-17-9-8-14(16-7-4-11-21-19(16)17)13-20-12-10-18(24)22-15-5-2-1-3-6-15/h1-9,11,20,23H,10,12-13H2,(H,22,24)

Standard InChI Key:  JHRCJZZKBSTEIG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   18.2439   -4.1089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9520   -4.5179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6629   -3.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6637   -4.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5318   -4.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8202   -4.1078    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1081   -4.5158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3966   -4.1067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6844   -4.5147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9729   -4.1055    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6838   -5.3360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9735   -3.2842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6847   -2.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6857   -2.0538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9737   -1.6438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2592   -2.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2617   -2.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2451   -3.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9491   -2.8734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9471   -2.0576    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2418   -1.6526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5329   -2.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5384   -2.8797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3733   -2.8665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 18  1  2  0
  1  2  1  0
  2  4  2  0
  3 19  2  0
  3  4  1  0
  1  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
  3 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4529344

   ---

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: 321.38

Molecular Weight (Monoisotopic): 321.1477

AlogP: 3.06

#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: 8.51

CX Basic pKa: 9.30

CX LogP: 1.87

CX LogD: 0.99

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.61

Np Likeness Score: -1.10

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