7-Fluoro-4-hydroxy-quinoline-3-carboxylic acid

ID: ALA345688

Cas Number: 63463-20-7

PubChem CID: 328521

Product Number: F337568, Order Now?

Max Phase: Preclinical

Molecular Formula: C10H6FNO3

Molecular Weight: 207.16

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C10H6FNO3/c11-5-1-2-6-8(3-5)12-4-7(9(6)13)10(14)15/h1-4H,(H,12,13)(H,14,15)

Standard InChI Key:  FWIYSXZSVUTDIK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 15 16  0  0  0  0  0  0  0  0999 V2000
    3.6125   -3.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7125   -3.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8125   -3.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8125   -5.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7125   -5.5417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5167   -3.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6125   -5.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9125   -3.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9125   -5.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5167   -2.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0125   -5.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7125   -2.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4167   -3.9875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0125   -3.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8958   -5.5417    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  5  1  0
  5  7  2  0
  6  1  1  0
  7  1  1  0
  8  3  2  0
  9  4  2  0
 10  6  2  0
 11  9  1  0
 12  2  1  0
 13  6  1  0
 14  8  1  0
 15 11  1  0
  3  4  1  0
 14 11  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA345688

   7-Fluoro-4-hydroxyquinoline-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: 207.16

Molecular Weight (Monoisotopic): 207.0332

AlogP: 1.78

#Rotatable Bonds: 1

Polar Surface Area: 70.42

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.56

CX Basic pKa: 1.08

CX LogP: 2.28

CX LogD: -1.10

Aromatic Rings: 2

Heavy Atoms: 15

QED Weighted: 0.75

Np Likeness Score: -0.95

References

1. 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]

2. 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]

3. Zhang H, Daněk O, Makarov D, Rádl S, Kim D, Ledvinka J, Vychodilová K, Hlaváč J, Lefèbre J, Denis M, Rademacher C, Ménová P..  (2022)  Drug-like Inhibitors of DC-SIGN Based on a Quinolone Scaffold.,  13  (6.0): [PMID:35707152] [10.1021/acsmedchemlett.2c00067]

Source

Source(1):

• Scientific Literature