4-Hydroxy-7-(naphthalen-2-ylmethoxy)-quinoline-3-carboxylic acid

ID: ALA160455

Cas Number: 79807-93-5

PubChem CID: 328526

Max Phase: Preclinical

Molecular Formula: C21H15NO4

Molecular Weight: 345.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cnc2cc(OCc3ccc4ccccc4c3)ccc2c1O

Standard InChI:  InChI=1S/C21H15NO4/c23-20-17-8-7-16(10-19(17)22-11-18(20)21(24)25)26-12-13-5-6-14-3-1-2-4-15(14)9-13/h1-11H,12H2,(H,22,23)(H,24,25)

Standard InChI Key:  QUXDLMJXPRKFCH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    7.6417   -3.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7417   -4.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7417   -5.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6417   -5.6042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4500   -3.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5417   -5.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8417   -3.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8417   -5.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4417   -5.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4500   -2.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417   -5.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9417   -5.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4292   -6.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6417   -2.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3375   -7.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0417   -5.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375   -5.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3500   -4.0500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9417   -4.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417   -5.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375   -6.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4500   -5.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4708   -7.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3583   -5.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3583   -6.6042    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 18  2  0
 13  9  1  0
 14 16  1  0
 15  2  1  0
 16 22  2  0
 17 13  1  0
 18 21  1  0
 19  6  1  0
 20  8  1  0
 21 17  1  0
 22 18  1  0
 23 10  2  0
 24 14  2  0
 25 23  1  0
 26 24  1  0
  3  4  1  0
 20 13  2  0
 14 10  1  0
 25 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA160455

   7-(naphthalen-2-ylmethoxy)-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: 345.35

Molecular Weight (Monoisotopic): 345.1001

AlogP: 4.37

#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: 4.69

CX LogD: 1.32

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.57

Np Likeness Score: -0.48

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