4-Hydroxy-7-[2-(naphthalen-2-yloxy)-ethoxy]-quinoline-3-carboxylic acid

ID: ALA156707

Cas Number: 79807-95-7

PubChem CID: 328536

Max Phase: Preclinical

Molecular Formula: C22H17NO5

Molecular Weight: 375.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cnc2cc(OCCOc3ccc4ccccc4c3)ccc2c1O

Standard InChI:  InChI=1S/C22H17NO5/c24-21-18-8-7-17(12-20(18)23-13-19(21)22(25)26)28-10-9-27-16-6-5-14-3-1-2-4-15(14)11-16/h1-8,11-13H,9-10H2,(H,23,24)(H,25,26)

Standard InChI Key:  ASCGFMFCUMXIEK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    9.5750   -6.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6750   -6.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7750   -6.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7750   -7.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6750   -8.5042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4792   -6.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5750   -7.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8750   -6.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8750   -8.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3458   -8.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4792   -5.3875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5625   -7.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3458   -9.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9750   -7.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6750   -5.3875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5500  -10.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4625   -8.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3792   -6.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9750   -6.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4542   -9.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0667   -8.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3667   -7.9625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2458   -7.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2458  -10.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2667   -8.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1667   -7.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1458   -8.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1458   -9.5125    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 12  1  0
 11  6  2  0
 12 17  2  0
 13 16  1  0
 14  9  1  0
 15  2  1  0
 16 20  2  0
 17 22  1  0
 18  6  1  0
 19  8  1  0
 20 17  1  0
 21 14  1  0
 22 25  1  0
 23 10  2  0
 24 13  2  0
 25 26  1  0
 26 21  1  0
 27 23  1  0
 28 24  1  0
  3  4  1  0
 19 14  2  0
 10 13  1  0
 27 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA156707

   7-(2-naphthalen-2-yloxyethoxy)-4-oxo-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: 375.38

Molecular Weight (Monoisotopic): 375.1107

AlogP: 4.25

#Rotatable Bonds: 6

Polar Surface Area: 88.88

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.76

CX Basic pKa: 1.56

CX LogP: 4.61

CX LogD: 1.24

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.49

Np Likeness Score: -0.49

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]

Source

Source(1):

• Scientific Literature