6,7-difluoro-2-((3-fluorophenyl)amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

ID: ALA5287693

Max Phase: Preclinical

Molecular Formula: C16H9F3N2O3

Molecular Weight: 334.25

Names and Identifiers

Canonical SMILES:  O=C(O)c1c(Nc2cccc(F)c2)[nH]c2cc(F)c(F)cc2c1=O

Standard InChI:  InChI=1S/C16H9F3N2O3/c17-7-2-1-3-8(4-7)20-15-13(16(23)24)14(22)9-5-10(18)11(19)6-12(9)21-15/h1-6H,(H,23,24)(H2,20,21,22)

Standard InChI Key:  CRCRMWLBMSSVRX-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   -2.1421    1.2364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4275    1.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7156    1.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7156    0.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4257   -0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1421    0.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0009    1.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7137    1.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7137    0.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0009   -0.0010    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0009    2.4746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4283    1.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4283    2.4746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1430    1.2367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4283   -0.0010    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4283   -0.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1429   -1.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1421   -2.0618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4273   -2.4746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7153   -2.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7106   -1.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8568   -2.4744    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8568    1.6490    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8568   -0.0047    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  3  7  1  0
  8  7  1  0
  9  8  2  0
 10  9  1  0
  4 10  1  0
  7 11  2  0
  8 12  1  0
 12 13  2  0
 12 14  1  0
  9 15  1  0
 15 16  1  0
 17 16  2  0
 18 17  1  0
 19 18  2  0
 20 19  1  0
 21 20  2  0
 16 21  1  0
 18 22  1  0
  1 23  1  0
  6 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5287693

   ---

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: 334.25

Molecular Weight (Monoisotopic): 334.0565

AlogP: 3.39

#Rotatable Bonds: 3

Polar Surface Area: 82.19

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.52

CX Basic pKa: ┄

CX LogP: 3.54

CX LogD: 1.66

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.69

Np Likeness Score: -0.95

References

1. Shin YS, Lee JY, Jeon S, Myung S, Gong HJ, Kim S, Kim HR, Jeong LS, Park CM..  (2023)  Discovery of 2-aminoquinolone acid derivatives as potent inhibitors of SARS-CoV-2.,  85  [PMID:36870624] [10.1016/j.bmcl.2023.129214]

Source

Source(1):

• Scientific Literature