4-{[(5-Chloro-8-hydroxyquinolin-7-yl)methyl]amino}-N-[2-(2-methyl-1H-indol-3-yl)ethyl]butanamide

ID: ALA4574404

PubChem CID: 155563771

Max Phase: Preclinical

Molecular Formula: C25H27ClN4O2

Molecular Weight: 450.97

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1[nH]c2ccccc2c1CCNC(=O)CCCNCc1cc(Cl)c2cccnc2c1O

Standard InChI:  InChI=1S/C25H27ClN4O2/c1-16-18(19-6-2-3-8-22(19)30-16)10-13-28-23(31)9-5-11-27-15-17-14-21(26)20-7-4-12-29-24(20)25(17)32/h2-4,6-8,12,14,27,30,32H,5,9-11,13,15H2,1H3,(H,28,31)

Standard InChI Key:  WPNHTKMCALCYSY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   33.6231  -13.8179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6220  -14.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3300  -15.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3282  -13.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0368  -13.8143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0376  -14.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7461  -15.0404    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.4544  -14.6296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4497  -13.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7406  -13.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3319  -15.8636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.3258  -12.5919    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   32.9139  -15.0455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2066  -14.6363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.4985  -15.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7911  -14.6352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0831  -15.0433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3757  -14.6341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6677  -15.0421    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.3764  -13.8169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9603  -14.6330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9610  -13.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2536  -13.4066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9591  -13.1326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.5055  -13.7402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3682  -12.4251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1662  -12.5959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7110  -11.9909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4592  -11.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6573  -11.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1160  -11.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3355  -14.5395    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
 18 19  1  0
 18 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 27  1  0
 26 24  1  0
 24 25  1  0
 25 23  2  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 25 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4574404

   ---

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: 450.97

Molecular Weight (Monoisotopic): 450.1823

AlogP: 4.61

#Rotatable Bonds: 9

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: 7.10

CX Basic pKa: 10.24

CX LogP: 2.65

CX LogD: 2.50

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.28

Np Likeness Score: -0.86

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