3-(4-sulfamoylphenyl)quinoline-5,8-dicarboxylic acid

ID: ALA5269222

Max Phase: Preclinical

Molecular Formula: C17H12N2O6S

Molecular Weight: 372.36

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)c1ccc(-c2cnc3c(C(=O)O)ccc(C(=O)O)c3c2)cc1

Standard InChI:  InChI=1S/C17H12N2O6S/c18-26(24,25)11-3-1-9(2-4-11)10-7-14-12(16(20)21)5-6-13(17(22)23)15(14)19-8-10/h1-8H,(H,20,21)(H,22,23)(H2,18,24,25)

Standard InChI Key:  NWFCZYSMPRVXCN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   -3.1997    0.0557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1997   -0.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4862   -1.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7787   -0.7657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7787    0.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4879    0.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4879    1.2882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1997    1.6991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7760    1.6991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0689    0.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568    0.0545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568   -0.7632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0638   -1.1781    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3550    0.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0667    0.0540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7762    0.4641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7766    1.2863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0684    1.6955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3554    1.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4862   -1.9978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7742   -2.4087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1979   -2.4087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4881    1.6971    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.1997    1.2863    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0773    2.4087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8990    2.4087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  1  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  5 10  1  0
 11 10  2  0
 12 11  1  0
 13 12  2  0
  4 13  1  0
 11 14  1  0
 15 14  2  0
 16 15  1  0
 17 16  2  0
 18 17  1  0
 19 18  2  0
 14 19  1  0
  3 20  1  0
 20 21  2  0
 20 22  1  0
 17 23  1  0
 23 24  1  0
 23 25  2  0
 23 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5269222

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 372.36

Molecular Weight (Monoisotopic): 372.0416

AlogP: 1.95

#Rotatable Bonds: 4

Polar Surface Area: 147.65

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.30

CX Basic pKa: 0.20

CX LogP: 1.70

CX LogD: -4.95

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.63

Np Likeness Score: -0.71

References

1. Van de Walle T, Cools L, Mangelinckx S, D'hooghe M..  (2021)  Recent contributions of quinolines to antimalarial and anticancer drug discovery research.,  226  [PMID:34655985] [10.1016/j.ejmech.2021.113865]

Source

Source(1):

• Scientific Literature