6-Methoxy-4-((4-(3-morpholinopropoxy)phenyl)amino)quinoline-3-carboxylic acid

ID: ALA3628456

PubChem CID: 122193470

Max Phase: Preclinical

Molecular Formula: C24H27N3O5

Molecular Weight: 437.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2ncc(C(=O)O)c(Nc3ccc(OCCCN4CCOCC4)cc3)c2c1

Standard InChI:  InChI=1S/C24H27N3O5/c1-30-19-7-8-22-20(15-19)23(21(16-25-22)24(28)29)26-17-3-5-18(6-4-17)32-12-2-9-27-10-13-31-14-11-27/h3-8,15-16H,2,9-14H2,1H3,(H,25,26)(H,28,29)

Standard InChI Key:  OMFICQJAXLCFDK-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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    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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  -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
    3.8942   -1.4964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9326   -0.8949    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
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  3 11  1  0
 14 15  1  0
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 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
 31 32  1  0
  7 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3628456

   ---

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: 437.50

Molecular Weight (Monoisotopic): 437.1951

AlogP: 3.79

#Rotatable Bonds: 9

Polar Surface Area: 93.15

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.26

CX Basic pKa: 7.58

CX LogP: 2.02

CX LogD: 2.04

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.49

Np Likeness Score: -1.29

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