N-(4-chlorophenyl)-8-hydroxyquinoline-5-sulfonamide

ID: ALA5271301

Max Phase: Preclinical

Molecular Formula: C15H11ClN2O3S

Molecular Weight: 334.78

Names and Identifiers

Canonical SMILES:  O=S(=O)(Nc1ccc(Cl)cc1)c1ccc(O)c2ncccc12

Standard InChI:  InChI=1S/C15H11ClN2O3S/c16-10-3-5-11(6-4-10)18-22(20,21)14-8-7-13(19)15-12(14)2-1-9-17-15/h1-9,18-19H

Standard InChI Key:  ROHAVZBFQQNXEN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -1.3592    0.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0737    0.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7881    0.4122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7881   -0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0737   -0.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3592   -0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0737    1.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6452    1.9796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3592    2.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6448    1.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6448    0.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0700    0.4119    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0700   -0.4133    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7853   -0.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4990   -0.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2159   -0.8232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2159   -1.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5023   -2.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7853   -1.6511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7881   -1.9770    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.8967    0.4119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4826    1.1266    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
  7  2  1  0
  7  8  1  0
  9  7  2  0
 10  9  1  0
 11 10  2  0
  1 11  1  0
 12 11  1  0
 13 12  1  0
 14 13  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 14  2  0
 20 17  1  0
 12 21  2  0
 12 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5271301

   ---

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: 334.78

Molecular Weight (Monoisotopic): 334.0179

AlogP: 3.39

#Rotatable Bonds: 3

Polar Surface Area: 79.29

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.54

CX Basic pKa: 2.23

CX LogP: 2.92

CX LogD: 2.69

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.77

Np Likeness Score: -1.51

References

1. Joaquim AR, Gionbelli MP, Gosmann G, Fuentefria AM, Lopes MS, Fernandes de Andrade S..  (2021)  Novel Antimicrobial 8-Hydroxyquinoline-Based Agents: Current Development, Structure-Activity Relationships, and Perspectives.,  64  (22.0): [PMID:34779640] [10.1021/acs.jmedchem.1c01318]

Source

Source(1):

• Scientific Literature