4-Hydroxy-7-sulfo-quinoline-3-carboxylic acid

ID: ALA1161215

Cas Number: 63463-28-5

PubChem CID: 328524

Max Phase: Preclinical

Molecular Formula: C10H7NO6S

Molecular Weight: 269.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cnc2cc(S(=O)(=O)O)ccc2c1O

Standard InChI:  InChI=1S/C10H7NO6S/c12-9-6-2-1-5(18(15,16)17)3-8(6)11-4-7(9)10(13)14/h1-4H,(H,11,12)(H,13,14)(H,15,16,17)

Standard InChI Key:  RJBZLMIRRDZOGV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
    3.3792   -3.6292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.9750   -2.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4542   -2.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9375   -2.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9375   -3.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9000   -3.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4542   -3.6167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4917   -2.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9750   -3.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4167   -3.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7250   -4.1292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4167   -2.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9042   -4.2042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8417   -2.9542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9000   -2.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4917   -1.8167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4542   -1.8167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125   -2.7167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4 12  2  0
  5 10  2  0
  6  1  1  0
  7  5  1  0
  8  2  1  0
  9  7  2  0
 10  6  1  0
 11  1  1  0
 12 15  1  0
 13  1  2  0
 14  1  2  0
 15  6  2  0
 16  8  2  0
 17  3  1  0
 18  8  1  0
  5  4  1  0
  2  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1161215

   4-oxo-7-sulfo-1H-quinoline-3-carboxylic acid

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: 269.23

Molecular Weight (Monoisotopic): 268.9994

AlogP: 0.89

#Rotatable Bonds: 2

Polar Surface Area: 124.79

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -4.32

CX Basic pKa: 1.20

CX LogP: -1.17

CX LogD: -4.44

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.69

Np Likeness Score: -0.68

References

1. Dove S, Coats E, Scharfenberg P, Franke R..  (1985)  7-substituted-4-hydroxyquinoline-3-carboxylic acids as inhibitors of dehydrogenase enzymes and of the respiration of Ehrlich ascites tumor cells: multivariate analysis and quantitative structure-activity relationship for polar substituents.,  28  (4): [PMID:3981536] [10.1021/jm00382a010]

2. Coats EA, Shah KJ, Milstein SR, Genther CS, Nene DM, Roesener J, Schmidt J, Pleiss M, Wagner E, Baker JK..  (1982)  4-hydroxyquinoline-3-carboxylic acids as inhibitors of cell respiration. 2. Quantitative structure-activity relationship of dehydrogenase enzyme and Ehrlich ascites tumor cell inhibitions.,  25  (1): [PMID:7086823] [10.1021/jm00343a011]

3. Shah KJ, Coats EA..  (1977)  Design, synthesis, and correlation analysis of 7-substituted 4-hydroxyquinoline-3-carboxylic acids as inhibitors of cellular respiration.,  20  (8): [PMID:894670] [10.1021/jm00218a003]

Source

Source(1):

• Scientific Literature