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

ID: ALA347711

Cas Number: 28027-17-0

PubChem CID: 257714

Product Number: H183401, Order Now?

Max Phase: Preclinical

Molecular Formula: C11H9NO4

Molecular Weight: 219.20

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c(O)c(C(=O)O)cnc2c1

Standard InChI:  InChI=1S/C11H9NO4/c1-16-6-2-3-7-9(4-6)12-5-8(10(7)13)11(14)15/h2-5H,1H3,(H,12,13)(H,14,15)

Standard InChI Key:  QROPNBKULZRDMD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 16 17  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
   -0.8875   -5.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7958   -5.0250    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  6  1  0
 14  8  1  0
 15 11  1  0
 16 15  1  0
  3  4  1  0
 14 11  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA347711

   4-Hydroxy-7-methoxyquinoline-3-carboxylic acid

Molecule Features

Natural Product: Yes

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: 219.20

Molecular Weight (Monoisotopic): 219.0532

AlogP: 1.65

#Rotatable Bonds: 2

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: 3.77

CX Basic pKa: 1.58

CX LogP: 1.98

CX LogD: -1.39

Aromatic Rings: 2

Heavy Atoms: 16

QED Weighted: 0.80

Np Likeness Score: -0.37

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. Erickson EH, Hainline CF, Lenon LS, Matson CJ, Rice TK, Swingle KE, Van Winkle M..  (1979)  Inhibition of rat passive cutaneous anaphylaxis by 3-(tetrazol-5-yl)quinolines.,  22  (7): [PMID:109613] [10.1021/jm00193a013]

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