7-[2-(4-Fluoro-phenoxy)-ethoxy]-4-hydroxy-quinoline-3-carboxylic acid

ID: ALA155672

Cas Number: 78105-15-4

PubChem CID: 328537

Max Phase: Preclinical

Molecular Formula: C18H14FNO5

Molecular Weight: 343.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cnc2cc(OCCOc3ccc(F)cc3)ccc2c1O

Standard InChI:  InChI=1S/C18H14FNO5/c19-11-1-3-12(4-2-11)24-7-8-25-13-5-6-14-16(9-13)20-10-15(17(14)21)18(22)23/h1-6,9-10H,7-8H2,(H,20,21)(H,22,23)

Standard InChI Key:  NCJQXDYIMVDHDG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    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
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    6.8750   -8.5042    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
    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
   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
   -0.3458   -9.5125    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
   -1.2500  -10.0292    0.0000 F   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
   -0.3458   -8.4667    0.0000 C   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
    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
    4.1667   -7.9750    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
  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 18  1  0
 16 23  1  0
 17 15  1  0
 18 21  2  0
 19 20  1  0
 20 16  2  0
 21 16  1  0
 22 11  1  0
 23 25  1  0
 24 22  1  0
 25 24  1  0
  3  4  1  0
 14 11  2  0
 19 15  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA155672

   7-[2-(4-fluorophenoxy)ethoxy]-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: 343.31

Molecular Weight (Monoisotopic): 343.0856

AlogP: 3.24

#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: 3.76

CX LogD: 0.39

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.67

Np Likeness Score: -0.87

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. Schuster D, Markt P, Grienke U, Mihaly-Bison J, Binder M, Noha SM, Rollinger JM, Stuppner H, Bochkov VN, Wolber G..  (2011)  Pharmacophore-based discovery of FXR agonists. Part I: Model development and experimental validation.,  19  (23): [PMID:22018919] [10.1016/j.bmc.2011.09.056]

Source

Source(1):

• Scientific Literature