4-((4-(3-(4-Ethylpiperazin-1-yl)propoxy)phenyl)amino)quinoline-3-carboxylic acid

ID: ALA3628522

PubChem CID: 122193523

Max Phase: Preclinical

Molecular Formula: C25H30N4O3

Molecular Weight: 434.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN1CCN(CCCOc2ccc(Nc3c(C(=O)O)cnc4ccccc34)cc2)CC1

Standard InChI:  InChI=1S/C25H30N4O3/c1-2-28-13-15-29(16-14-28)12-5-17-32-20-10-8-19(9-11-20)27-24-21-6-3-4-7-23(21)26-18-22(24)25(30)31/h3-4,6-11,18H,2,5,12-17H2,1H3,(H,26,27)(H,30,31)

Standard InChI Key:  FSPXQXFCDSPPRX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   -1.2964    1.4973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9122   -1.4966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9506   -0.8952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2907   -2.9981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5870   -3.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5835   -5.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8807   -6.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1815   -5.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1852   -3.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8880   -3.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4810   -6.0117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7815   -5.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0810   -6.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3815   -5.2644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2755   -7.5217    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2791   -6.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9819   -5.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6810   -6.0154    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6774   -7.5154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9746   -8.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9138   -2.4966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -15.5719   -8.2779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.5672   -9.4779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  1 10  1  0
  5 10  1  0
 11 12  2  0
  3 11  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 14 19  2  0
 21 22  1  0
 22 23  1  0
 20 21  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 24 29  1  0
 23 27  1  0
 17 20  1  0
 13 14  1  0
  4 13  1  0
 11 30  1  0
 24 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3628522

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 434.54

Molecular Weight (Monoisotopic): 434.2318

AlogP: 4.08

#Rotatable Bonds: 9

Polar Surface Area: 77.93

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.02

CX Basic pKa: 8.34

CX LogP: 2.08

CX LogD: 2.02

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.49

Np Likeness Score: -1.30

References

1. Medapi B, Suryadevara P, Renuka J, Sridevi JP, Yogeeswari P, Sriram D..  (2015)  4-Aminoquinoline derivatives as novel Mycobacterium tuberculosis GyrB inhibitors: Structural optimization, synthesis and biological evaluation.,  103  [PMID:26318054] [10.1016/j.ejmech.2015.06.032]

Source

Source(1):

• Scientific Literature