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

ID: ALA157710

Cas Number: 17825-22-8

PubChem CID: 328505

Max Phase: Preclinical

Molecular Formula: C17H13NO4

Molecular Weight: 295.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cnc2cc(OCc3ccccc3)ccc2c1O

Standard InChI:  InChI=1S/C17H13NO4/c19-16-13-7-6-12(22-10-11-4-2-1-3-5-11)8-15(13)18-9-14(16)17(20)21/h1-9H,10H2,(H,18,19)(H,20,21)

Standard InChI Key:  ABQKYBVDVAXVNO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  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
   -0.8958   -5.5417    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
   -1.7958   -5.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6958   -5.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5875   -4.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6958   -6.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5958   -7.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4958   -5.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5000   -6.5542    0.0000 C   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 11  1  0
 14  6  1  0
 15  8  1  0
 16 13  1  0
 17 16  1  0
 18 17  2  0
 19 17  1  0
 20 19  2  0
 21 18  1  0
 22 20  1  0
  3  4  1  0
 15 11  2  0
 21 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA157710

   4-Hydroxy-7-benzyloxyquinoline-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: 295.29

Molecular Weight (Monoisotopic): 295.0845

AlogP: 3.22

#Rotatable Bonds: 4

Polar Surface Area: 79.65

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.76

CX Basic pKa: 1.56

CX LogP: 3.70

CX LogD: 0.33

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.77

Np Likeness Score: -0.55

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. PubChem BioAssay data set, 

3. PubChem BioAssay data set, 

4. PubChem BioAssay data set, 

5. 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(2):

• Scientific Literature
• PubChem BioAssays