3-{[(5-Chloro-8-hydroxyquinolin-7-yl)methyl]amino}-N-[2-(2-methyl-1H-indol-3-yl)ethyl]propanamide

ID: ALA4526272

PubChem CID: 155544079

Max Phase: Preclinical

Molecular Formula: C24H25ClN4O2

Molecular Weight: 436.94

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1[nH]c2ccccc2c1CCNC(=O)CCNCc1cc(Cl)c2cccnc2c1O

Standard InChI:  InChI=1S/C24H25ClN4O2/c1-15-17(18-5-2-3-7-21(18)29-15)8-12-27-22(30)9-11-26-14-16-13-20(25)19-6-4-10-28-23(19)24(16)31/h2-7,10,13,26,29,31H,8-9,11-12,14H2,1H3,(H,27,30)

Standard InChI Key:  GOABROPOBRHMRM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   17.9768  -14.3297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9756  -15.1534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6878  -15.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6860  -13.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3946  -14.3261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3954  -15.1492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1081  -15.5563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.8205  -15.1455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8157  -14.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1025  -13.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6897  -16.3836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6836  -13.0954    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.2635  -15.5614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5520  -15.1522    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8398  -15.5603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1283  -15.1511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4161  -15.5592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7046  -15.1500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4155  -16.3805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7053  -14.3287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4174  -13.9165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4181  -13.0952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0065  -11.8270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7494  -12.6081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8279  -11.8276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0777  -12.6074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8769  -12.7817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4271  -12.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1685  -11.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3699  -11.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9721  -12.8645    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  1  0
 21 22  1  0
 22 26  1  0
 25 23  1  0
 23 24  1  0
 24 22  2  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 24 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4526272

   ---

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: 436.94

Molecular Weight (Monoisotopic): 436.1666

AlogP: 4.22

#Rotatable Bonds: 8

Polar Surface Area: 90.04

Molecular Species: BASE

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.12

CX Basic pKa: 9.59

CX LogP: 2.36

CX LogD: 2.24

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.31

Np Likeness Score: -0.97

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