6-Fluoro-4-((4-((3-morpholinopropyl)amino)phenyl)amino)quinoline-3-carboxylic acid

ID: ALA3628520

PubChem CID: 122193521

Max Phase: Preclinical

Molecular Formula: C23H25FN4O3

Molecular Weight: 424.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cnc2ccc(F)cc2c1Nc1ccc(NCCCN2CCOCC2)cc1

Standard InChI:  InChI=1S/C23H25FN4O3/c24-16-2-7-21-19(14-16)22(20(15-26-21)23(29)30)27-18-5-3-17(4-6-18)25-8-1-9-28-10-12-31-13-11-28/h2-7,14-15,25H,1,8-13H2,(H,26,27)(H,29,30)

Standard InChI Key:  HAVLBPZXTFNRAU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    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
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   -2.5870   -3.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -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 O   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
    3.6321   -1.3486    0.0000 F   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
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 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
  7 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3628520

   ---

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: 424.48

Molecular Weight (Monoisotopic): 424.1911

AlogP: 3.95

#Rotatable Bonds: 8

Polar Surface Area: 86.72

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.24

CX Basic pKa: 7.42

CX LogP: 1.51

CX LogD: 1.42

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.47

Np Likeness Score: -1.63

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