3-(5-fluoro-2-methoxyphenyl)quinoline-5,8-dicarboxylic acid

ID: ALA5266075

Max Phase: Preclinical

Molecular Formula: C18H12FNO5

Molecular Weight: 341.29

Names and Identifiers

Canonical SMILES:  COc1ccc(F)cc1-c1cnc2c(C(=O)O)ccc(C(=O)O)c2c1

Standard InChI:  InChI=1S/C18H12FNO5/c1-25-15-5-2-10(19)7-13(15)9-6-14-11(17(21)22)3-4-12(18(23)24)16(14)20-8-9/h2-8H,1H3,(H,21,22)(H,23,24)

Standard InChI Key:  IBLMIBIZDDHULI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   -2.4890    0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4890   -0.8235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7755   -1.2301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0680   -0.8199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0680    0.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7771    0.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7771    1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4890    1.6448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0653    1.6448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3582    0.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539    0.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539   -0.8174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3531   -1.2324    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0657    0.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7774   -0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4869    0.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4873    1.2320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7791    1.6413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0661    1.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7755   -2.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0635   -2.4629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4872   -2.4629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7791    2.4629    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.7774   -0.8219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4890   -1.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  1  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  5 10  1  0
 11 10  2  0
 12 11  1  0
 13 12  2  0
  4 13  1  0
 11 14  1  0
 15 14  2  0
 16 15  1  0
 17 16  2  0
 18 17  1  0
 19 18  2  0
 14 19  1  0
  3 20  1  0
 20 21  2  0
 20 22  1  0
 18 23  1  0
 15 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5266075

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 341.29

Molecular Weight (Monoisotopic): 341.0700

AlogP: 3.45

#Rotatable Bonds: 4

Polar Surface Area: 96.72

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.30

CX Basic pKa: 0.08

CX LogP: 3.08

CX LogD: -3.57

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.75

Np Likeness Score: -0.54

References

1. Van de Walle T, Cools L, Mangelinckx S, D'hooghe M..  (2021)  Recent contributions of quinolines to antimalarial and anticancer drug discovery research.,  226  [PMID:34655985] [10.1016/j.ejmech.2021.113865]

Source

Source(1):

• Scientific Literature